US 20140.031228A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2014/0031228A1 Mann et al. (43) Pub. Date: Jan. 30, 2014

(54) HERBICIDAL COMPOSITIONS (52) U.S. Cl. COMPRISING CPC ...... A0IN 43/40 (2013.01) 4-AMINO-3-CHLORO-5-FLUORO-6-(4- USPC ...... SO4/130 CHLORO-2-FLUORO-3-METHOXYPHENYL) (57) ABSTRACT PYRONE-2-CARBOXYLIC ACID ORA Provided herein are synergistic herbicidal compositions con DERVATIVE THEREOF AND ACETYL-COA taining and methods utilizing (a) a compound of formula (I): CARBOXYLASE (ACCASE) INHIBITORS (71) Applicant: DOWAGROSCIENCES LLC, Indianapolis, IN (US) (I) (72) Inventors: Richard K. Mann, Franklin, IN (US); Carla N. Yerkes, Crawfordsville, IN (US); Monte R. Weimer, Pittsboro, IN (US); Nelson M. Carranza, Ibague (CO) (73) Assignee: DOWAGROSCIENCES LLC, Indianapolis, IN (US) (21) Appl. No.: 13/839,043 or an agriculturally acceptable salt or thereof and (b) an (22) Filed: Mar 15, 2013 ACCase inhibitors, including. e.g., clethodim, clodinafop propargyl, cyhalofop-R-butyl, diclofop-methyl, fenoxaprop Related U.S. Application Data P-ethyl, -P-butyl, haloxyfop-R-methyl, metamifop, pinoxaden, profoxydim, quizalofop-P-ethyl, Sethoxydimand (60) Provisional application No. 61/675,103, filed on Jul. tralkoxydim, provide synergistic weed control of undesirable 24, 2012. Vegetation in rice, cereals, wheat, barley, oats, rye, Sorghum, corn/maize, Sugarcane, Sunflower, oilseed rape, canola, Sugar Publication Classification beet, soybean, cotton, pineapple, pastures, grasslands, range lands, fallowland, turf, tree and vine orchards, aquatics, plan (51) Int. Cl. tation crops, vegetables, industrial vegetation management AOIN 43/40 (2006.01) (IVM) or rights of way (ROW). US 2014/003 1228A1 Jan. 30, 2014

HERBICIDAL COMPOSITIONS 0008 A fifth embodiment includes compositions of the COMPRISING first, second, third, or fourth embodiments, wherein (b) is 4-AMINO-3-CHLORO-5-FLUORO-6-(4- selected from the group consisting of clethodim, clodinafop CHLORO-2-FLUORO-3-METHOXYPHENYL) propargyl, cyhalofop-R-butyl, diclofop-methyl, fenoxaprop PYRONE-2-CARBOXYLIC ACID ORA P-ethyl, fluazifop-P-butyl, haloxyfop-R-methyl, metamifop, DERVATIVE THEREOF AND ACETYL-COA pinoxaden, profoxydim, quizalofop-P-ethyl, or CARBOXYLASE (ACCASE) INHIBITORS tralkoxydim. 0009. A sixth embodiment includes a composition of the PRIORITY CLAIM first embodiment, wherein (a) is the compound of formula (I) 0001. This application claims the benefit of U.S. provi or an agriculturally acceptable benzyl ester and (b) is sional patent application No. 61/675,103 filed on Jul. 24. clethodim. 2012, this provisional application is incorporated herein by 0010. A seventh embodiment includes a composition of the reference in its entirety. first embodiment, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is clodin FIELD afop-propargyl. 0002 Provided herein are herbicidal compositions com 0011. An eighth embodiment includes a compositon of the prising and methods of controlling undesirable vegetation first embodiment, wherein (a) is the compound of formula (I) utilizing (a) 4-amino-3-chloro-5-fluoro-6-(4-chloro-2- or an agriculturally acceptable benzyl ester and (b) is cyha fluoro-3-methoxyphenyl)-2-carboxylic acid or an lofop-R-butyl. 0012. An ninth embodiment includes a composition of the agriculturally acceptable ester or salt thereof and (b) an first embodiment, wherein (a) is the compound of formula (I) acetyl-CoA carboxylase (ACCase) inhibitor. or an agriculturally acceptable benzyl ester and (b) is diclo BACKGROUND fop-methyl. 0013 Antenth embodiment includes a composition of the 0003. The protection of crops from weeds and other veg first embodiment, wherein (a) is the compound of formula (I) etation which inhibit crop growth is a constantly recurring or an agriculturally acceptable benzyl ester and (b) is fenox problem in agriculture. To help combat this problem, aprop-P-ethyl. researchers in the field of synthetic chemistry have produced 0014. An eleventh embodiment includes a composition of an extensive variety of chemicals and chemical formulations the first embodiment, wherein(a) is the compound of formula effective in the control of such unwanted growth. Chemical (I) or an agriculturally acceptable benzyl ester and (b) is of many types have been disclosed in the literature fluazifop-P-butyl. and a large number are in commercial use. However, there 0015. An twelfth embodiment includes a composition of remains a need for compositions and methods that are effec the first embodiment, wherein (a) is the compound of formula tive in controlling undesirable vegetation. (I) or an agriculturally acceptable benzyl ester and (b) is SUMMARY haloxyfop-R-methyl. 0016. A thirteenth embodiment includes a composition of 0004. A first embodiment includes herbicidal composi the first embodiment, wherein (a) is the compound of formula tions, comprising: a herbicidally effective amount of (a) a (I) or an agriculturally acceptable benzyl ester and (b) is compound of the formula (I) metamifop. 0017. A fourteenth embodiment includes a composition of the first embodiment, wherein (a) is the compound of formula (I) (I) or an agriculturally acceptable benzyl ester and (b) is pinoxaden. 0018. A fifteenth embodiment includes a composition of the first embodiment, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is profoxydim. 0019. A sixteenth embodiment includes a composition of the first embodiment, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is quizalofop-P-ethyl. 0020. A seventeenth embodiment includes a composition of the first embodiment, wherein (a) is the compound of or an agriculturally acceptable salt or ester thereof: and (b) formula (I) or an agriculturally acceptable benzyl ester and ACCase inhibitors, or a salt or ester thereof. (b) sethoxydim. 0005. A second embodiment includes a composition of 0021. An eighteenth embodiment includes a composition according to the first embodiment, wherein (a) is a C alkyl of the first embodiment, wherein (a) is the compound of or benzyl ester of compound (I). formula (I) or an agriculturally acceptable benzyl ester and 0006. A third embodiment includes a composition of (b) is tralkyoxydim. according to the first embodiment wherein (a) is a benzyl ester 0022. A nineteenth embodiment includes composition of compound (I). according to the first through the eighteenth embodiments 0007. A fourth embodiment includes a composition of further comprising a Safener. according to the first embodiment wherein (a) is the com 0023. A twenth embodiment includes a composition pound of formula (I), which is the carboxylic acid. according to the first embodiment wherein the ratios the com US 2014/003 1228A1 Jan. 30, 2014 pound of formula (I) or agriculturally acceptable salt or ester 0032. A twenty-ninth embodiment includes a composition thereof to clethodim or an agriculturally acceptable salt or according to the first embodiment wherein the ratios the com ester thereof, expressed in units of weigthto weight (g rog), pound of formula (I) or agriculturally acceptable salt or ester gae/ha to gai/ha, or gae/ha to gae/ha, are within the range of thereof toprofoxydim or an agriculturally acceptable salt or about 1:140 to about 9:1. ester thereof, expressed in units of weight to weight (g tog), 0024. A twenty-first embodiment includes a composition gae/ha to gai/ha, or gae/ha to gae/ha, are within the range of according to the first embodiment wherein the ratios the com about 1:70 to about 29:1. pound of formula (I) or agriculturally acceptable salt or ester 0033. A thirtieth embodiment includes a composition thereof to clodinafop-propargyl or an agriculturally accept according to the first embodiment wherein the ratios the com able salt or ester thereof, expressed in units of weight to pound of formula (I) or agriculturally acceptable salt or ester Weight (g to g), gae/ha to gai/ha, or gae/ha to gae/ha, are thereof to quizalofop-P-ethyl or an agriculturally acceptable within the range of about 1:40 to about 60:1. salt or ester thereof, expressed in units of weight to weight (g 0025 A twenty-second embodiment includes a composi to g), gae?ha to gai/ha, or gae/ha to gae/ha, are within the tion according to the first embodiment wherein the ratios the range of about 1:100 to about 12:1. compound of formula (I) or agriculturally acceptable salt or 0034. A thirty-first embodiment includes a composition ester thereof to cyhalofop-R-butyl oran agriculturally accept according to the first embodiment wherein the ratios the com able salt or ester thereof, expressed in units of weigth to pound of formula (I) or agriculturally acceptable salt or ester Weight (g to g), gae/ha to gai/ha, or gae/ha to gae/ha, are thereof to Sethoxydim or an agriculturally acceptable salt or ester thereof, expressed in units of weight to weight (g tog), within the range of about 1:155 to about 6:1. gae/ha to gai/ha, or gae/ha to gae/ha, are within the range of 0026. A twenty-third embodiment includes a composition about 1:70 to about 29:1. according to the first embodiment wherein the ratios the com 0035 A thirty-second embodiment includes a composi pound of formula (I) or agriculturally acceptable salt or ester tion according to the first embodiment wherein the ratios the thereof to diclofop-methyl or an agriculturally acceptable salt compound of formula (I) or agriculturally acceptable salt or orester thereof, expressed in units of weight to weight (g tog), ester thereof to tralkoxydim or an agriculturally acceptable gae/ha to gai/ha, or gae/ha to gae/ha, are within the range of salt or ester thereof, expressed in units of weight to weight (g about 1:560 to about 5:1. to g), gae?ha to gai/ha, or gae/ha to gae/ha, are within the 0027. A twenty-fourth embodiment includes a composi range of about 1:38 to about 60:1. tion according to the first embodiment wherein the ratios the 0036) A thirty-third embodiment includes any composi compound of formula (I) or agriculturally acceptable salt or tion according to the first through the thirty-second embodi ester thereof to fenoxaprop-P-ethyl or an agriculturally ments that, further comprising an agriculturally acceptable acceptable Saltorester thereof, expressed in units of weight to adjuvant, and/or carrier and/or herbicide Safener. Weight (g to g), gae/ha to gai/ha, or gae/ha to gae/ha, are 0037. A thirty-fourth embodiment includes any composi within the range of about 1:170 to about 30:1, and the crop tion according to the first through the thirty-third embodi safeners isoxadifen-methyl and mefenpyr-diethyl are incor ments, wherein synergy between herbicides is determined by porated into the product. the Colby equation. 0028. A twenty-fifth embodiment includes a composition 0038 A thirty-fifth embodiment includes any composi according to the first embodiment wherein the ratios the com tion according to the first embodiment wherein (b) is cyhalo pound of formula (I) or agriculturally acceptable salt or ester fop-butyl or carboxylic acid, carboxylate salt, orester thereof, thereof to fluazifop-P-butyl or an agriculturally acceptable wherein the composition further comprises penoXSulam, ben salt or ester thereof, expressed in units of weight to weight (g taZon-sodium, , bispyribac-Sodium, imaZamox, ben to g), gae?ha to gai/ha, or gae/ha to gae/ha, are within the Zobicyclon, , , , benfuresate, range of about 1:210 to about 3:1. fentraZamide, indanofan, ipfencarbazone, mefenacet, 0029. A twenty-sixth embodiment includes a composition oxazichlomefone, pretilachlor, propyrisulfuron, pyraclonil. according to the first embodiment wherein the ratios the com pyriftalid, or pyrimisulfan, or an agriculturally acceptable pound of formula (I) or agriculturally acceptable salt or ester salt, carboxylic acid, carboxylate salt, or ester thereof, in thereof to haloxyfop-R-methyl or an agriculturally accept combination as a synergistic 3 way/ternary mixture. able salt or ester thereof, expressed in units of weight to 0039. A thirty-sixth embodiment includes any composi Weight (g to g), gae/ha to gai/ha, or gae/ha to gae/ha, are tion according to the first embodiment wherein (b) is fenox within the range of about 1:45 to about 10:1. aprop, metamifop, or profoxydim, or agriculturally accept 0030. A twenty-seventh embodiment includes a composi able salt, ester, carboxylate salt, or carboxylic acid thereof, tion according to the first embodiment wherein the ratios the wherein the composition further comprises penoXSulam, or compound of formula (I) or agriculturally acceptable salt or an agriculturally acceptable salt, carboxylic acid, carboxylate ester thereof to metamifop or an agriculturally acceptable salt salt, or ester thereof, in combination as a synergistic 3 way/ orester thereof, expressed in units of weight to weight (g tog), ternary mixture. gae/ha to gai/ha, or gae/ha to gae/ha, are within the range of 0040. A thirty-seventh embodiment includes methods for about 1:150 to about 6:1. controlling undesirable vegetation comprising the steps of 0031. A twenty-eighth embodiment includes a composi contacting the vegetation or the locus thereof with or applying tion according to the first embodiment wherein the ratios the to the soil or water to prevent the emergence or growth of compound of formula (I) or agriculturally acceptable salt or Vegetation the at least one composition according to the first ester thereof to pinoxaden oran agriculturally acceptable salt through the thirty-sixth embodiments. orester thereof, expressed in units of weight to weight (g tog), 0041. A thirty-eighth embodiment includes methods for gae/ha to gai/ha, or gae/ha to gae/ha, are within the range of controlling undesirable vegetation comprising the steps of about 1:30 to about 150:1. contacting the vegetation or the locus thereof with or applying US 2014/003 1228A1 Jan. 30, 2014 to the Soil or water to prevent the emergence or growth of lipid biosynthesis inhibitor-, photosystem I inhibitor-, photo Vegetation utilizing a herbicidally effective amount of (a) a system II inhibitor-, triazine-, or -tolerant crops. compound of the formula (I) 0049. The forty-sixth embodiment includes methods according to the forty-fifth embodiment, wherein the tolerant (I) crop possesses multiple or stacked traits conferring tolerance to multiple herbicides or multiple modes of action. 0050. The forty-seventh embodiment includes methods according to the thirty-seventh and thirty-eighth embodi ments, wherein the undesirable vegetation comprises a her bicide resistant or tolerant weed. 0051. The forty-eighth embodiment includes methods according to the forty-seventh embodiment, wherein the resistant or tolerant weed is a biotype with resistance or tolerance to multiple herbicides, multiple chemical classes, or multiple herbicide modes-of-action or via multiple resistance mechanisms. or an agriculturally acceptable salt or ester of thereof, and (b) an ACCase inhibitor. 0.052 The forty-ninth embodiment includes methods according to the forty-seventh embodiment wherein the resis 0042. The thirty-ninth embodiment includes methods of tant or tolerant weed is a biotype resistant or tolerant to the thirty-seventh and thirty-eighth embodiments, wherein acetolactate synthase (ALS) or acetohydroxy acid synthase the undesirable vegetation is controlled in rice, cereals, wheat, barley, oats, rye, Sorghum, corn/maize, Sugarcane, (AHAS) inhibitors, photosystem II inhibitors, acetyl CoA Sunflower, oilseed rape, canola, Sugar beet, soybean, cotton, carboxylase (ACCase) inhibitors, synthetic , pineapple, pastures, grasslands, rangelands, fallowland, turf, transport inhibitors, photosystem I inhibitors, 5-enolpyru tree and vine orchards, aquatics, plantation crops, vegetables, vylshikimate-3-phosphate (EPSP) synthase inhibitors, industrial vegetation management (IVM) or rights of way microtubule assembly inhibitors, fatty acid and lipid synthe sis inhibitors, protoporphyrinogen oxidase (PPO) inhibitors, (ROW). carotenoid biosynthesis inhibitors, very long chain fatty acid 0043 wherein the undesirable vegetation is immature. (VLCFA) inhibitors, phytoene desaturase (PDS) inhibitors, 0044) The forty-first embodiment includes methods of the glutamine synthetase inhibitors, 4-hydroxyphenyl-pyruvate thirty-seventh and thirty-eighth embodiments wherein the dioxygenase (HPPD) inhibitors, mitosis inhibitors, cellulose compounds (a) and (b) are applied to water. biosynthesis inhibitors, herbicides with multiple modes-of action, quinclorac, arylaminopropionic acids, difenZoquat, 0045. The forty-second embodiment includes methods according to the forty-first embodiment, wherein the water is , or organoarsenicals. part of a flooded rice paddy. 0053 Provided herein are herbicidal compositions com 0046. The forty-third embodiment includes methods prising a methods of controlling undesirable vegetation uti according to the thirty-seventh and thirty-eighth embodi lizing a herbicidally effective amount of (a) a compound of ments, wherein compounds (a) and (b) are applied pre-emer the formula (I). gently to the weed or crop.

0047. The forty-fourth embodiment includes methods (I) according to the thirty-seventh and thirty-eighth embodi ments, wherein compounds (a) and (b) are applied post-emer gently to the weed or crop. 0048. The forty-fifth embodiment includes methods according to the thirty-seventh and thirty-eighth embodi ments, wherein the undesirable vegetation is controlled in glyphosate-, 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitor-, glufosinate-, glutamine synthetase inhibitor-, -, phenoxy auxin-, pyridyloxy auxin-, synthetic auxin-, auxin transport inhibitor-, aryloxyphenox ypropionate-, cyclohexanedione-, phenylpyrazoline-, acetyl CoA carboxylase (ACCase) inhibitor-, imidazolinone-, sul fonylurea-, pyrimidinylthiobenzoate-, triazolopyrimidine-, or an agriculturally acceptable salt or ester of thereof, and (b) Sulfonylaminocarbonyltriazolinone-, acetolactate synthase an ACCase inhibitor. Exemplary ACCase inhibitors include, (ALS) or acetohydroxy acid synthase (AHAS) inhibitor but are not limited to, clethodim, clodinafop-propargyl, cyha 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor lofop-R-butyl, diclofop-methyl, fenoxaprop-P-ethyl, fluazi phytoene desaturase inhibitor-, carotenoid biosynthesis fop-P-butyl, haloxyfop-R-methyl, metamifop, pinoxaden, inhibitor-, protoporphyrinogen oxidase (PPO) inhibitor-, cel profoxydim, quizalofop-P-ethyl, Sethoxydim ortralkoxydim. lulose biosynthesis inhibitor-, mitosis inhibitor-, microtubule The compositions may also contain an agriculturally accept inhibitor-, very long chain fatty acid inhibitor-, fatty acid and able adjuvant or carrier. US 2014/003 1228A1 Jan. 30, 2014

DETAILED DESCRIPTION O Definitions C F O 0054 As used herein, the compound of formula (I) has the following structure: C2 O CH Sr. N O

(IH) 0059. This compound is described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of clodin afop-propargyl include its use as a herbicide for, e.g., post emergence control of annual grasses, including, e.g., Avena, Lolium, Setaria, Phalaris and Alopecurus spp., in cereals. 0060. As used herein, cyhalofop-butyl is butyl (2R)-2-4- (4-cyano-2-fluorophenoxy)phenoxypropanoate and pos sesses the following structure:

O NC O 1n 1\ The compound of formula (I) can be identified by the name O CH3 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)- CH 5-fluoropyridine-2-carboxylic acid and has been described in O U.S. Pat. No. 7,314,849 (B2), which is incorporated herein by reference in its entirety. Exemplary uses of the compound of F the formula (I) include controlling undesirable vegetation, including grass, broadleaf and sedge weeds, in multiple non 0061 This compound is described in The Pesticide crop and cropping situations. Manual, Fifteenth Edition, 2009. Exemplary uses of cyhalo 0055 Without being limited to any theory, ACCase inhibi fop-butyl include its use as a herbicide for, e.g., post-emer tors believed to inhibit to any extent acetyl coenzyme A gence control of annual and perennial grass weeds in seeded carboxylase (ACCase), an enzyme involved in fatty acid syn and transplanted rice. thesis. Exemplary ACCase inhibitors include, but are not 0062. As used herein, diclofop-methyl is methyl 2-4-(2, limited to aryloxyphenoxy propionates and the cyclohex 4-dichlorophenoxy)phenoxypropanoate and possesses the anediones. Further examples include, but are not limited to, following structure: clethodim, clodinafop-propargyl, cyhalofop-R-butyl, diclo fop-methyl, fenoxaprop-P-ethyl, fluazifop-P-butyl, haloxy fop-R-methyl, metamifop, pinoxaden, profoxydim, quizalo fop-P-ethyl, sethoxydim and tralkoxydim. 0056. As used herein, clethodim is 2-1-(2E)-3-chloro C C O CH3 2-propen-1-yloxy)iminopropyl-5-2-(ethylthio)propyl-3- hydroxy-2-cyclohexen-1-one and possesses the following CH3 Structure: O 0063. This compound is described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of diclo fop-methyl include its use as a herbicide for, e.g., post-emer O 's-n-CH gence control of wild oats, wild millets, and other annual CH3 grass weeds in wheat, barley, rye, red fescue, and broadleaf CropS. S OH 0064. As used herein, fenoxaprop-P-ethyl is ethyl (2R)-2- 4-(6-chloro-2-benzoxazolyl)oxyphenoxypropanoate and possesses the following structure: ls CH3

0057 This compound is described in Tomlin, C., ed. A C World Compendium The Pesticide Manual. 15" ed. Alton: O BCPC Publications, 2009 (hereafter “The Pesticide Manual, Fifteenth Edition, 2009.). Exemplary uses of clethodim O include its use as a herbicide for, e.g., post-emergence control O Sr. of annual and perennial grasses in broadleaf crops, Veg als CH etables, trees and vines. N O 0058 As used herein, clodinafop-propargyl is 2-propynyl (2R)-2-[4-(5-chloro-3-fluoro-2-pyridinyl)oxyphenoxy 0065. This compound is described in The Pesticide propanoate and possesses the following structure: Manual, Fifteenth Edition, 2009. Exemplary uses offenox US 2014/003 1228A1 Jan. 30, 2014 aprop-P-ethyl include its use as a herbicide for, e.g., control of 0072. As used herein, pinoxaden is 8-(2,6-diethyl-4-me annual and perennial grass weeds in crops including rice. thylphenyl)-1,2,4,5-tetrahydro-7-oxo-7H-pyrazolo 1,2-d1, 4.5oxadiazepin-9-yl-2,2-dimethylpropanoate and possesses 0066. As used herein, fluazifop-P-butyl is butyl (2R)-2-4- 5-(trifluoromethyl)-2-pyridinyloxyphenoxypropanoate the following structure: and possesses the following structure: CH

O

FC 21 NN --~~ O CH3 N O CH \U- /

CH3 0067. This compound is described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of fluazi CH3 fop-P-butyl include its use as a herbicide for, e.g., post-emer gence control of wild oats, Volunteer cereals, and annual and perennial grass weeds in oilseed rape, Sugar beet, fodderbeet, This compound is described in The Pesticide Manual, Fif potatoes, vegetables, cotton, Soya beans, pome fruit, stone teenth Edition, 2009. Exemplary uses of pinoxaden include fruit, bush fruit, vines, citrus fruit, pineapples, bananas, its use as a herbicide for, e.g., post-emergence control of Strawberries, Sunflowers, alfalfa, coffee, ornamentals and annual grasses, including Alopecurus, Apera, Avena, Lolium, other broadleaf crops. Fluazifop-P-butyl can be used in com Phalaris and Setaria spp., in wheat and barley. bination with Safeners, e.g., isoxadifen-ethyl or mefenpyr 0073. As used herein, profoxydim is 2-1-2-(4-chlo diethyl. rophenoxy)propoxyliminobutyl-3-hydroxy-5-(tetrahydro 0068. As used herein, haloxyfop-P-methyl is methyl (2R)- 2H-thiopyran-3-yl)-2-cyclohexen-1-one and possesses the 2-4-3-chloro-5-(trifluoromethyl)-2-pyridinyloxyphe following structure: noxypropanoate and possesses the following structure: C

N CH

C CH3

0069. This compound is described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of haloxy fop-P-methyl include its use as a herbicide for, e.g., post emergence control of annual and perennial grasses in a vari ety of crops. 0074 This compound is described in The Pesticide 0070. As used herein, metamifop is (2R)-2-[4-(6-chloro Manual, Fifteenth Edition, 2009. Exemplary uses of profoxy 2-benzoxazolyl)oxyphenoxy-N-(2-fluorophenyl)-N-meth dim include its use as a herbicide for, e.g., control of grass ylpropanamide and possesses the following structure: weeds in rice. 0075. As used herein, quizalofop-P-ethyl is ethyl (2R)-2- 4-(6-chloro-2-quinoxalinyl)oxyphenoxypropanoate and possesses the following structure:

C O

O 1N

0071. This compound is described in The Pesticide susCOrrN O CH3 Manual, Fifteenth Edition, 2009. Exemplary uses of metami fop include its use as a herbicide for, e.g., post-emergence control of annual and perennial grasses in a variety of crops, 0076. This compound is described in The Pesticide including rice. Manual, Fifteenth Edition, 2009. Exemplary uses of quizalo US 2014/003 1228A1 Jan. 30, 2014

fop-P-ethyl include its use as a herbicide for, e.g., selective broadcast, granular spot, shaker bottle, or stream spray) via post-emergence control of annual and perennial grass weeds hand, backpack, machine, tractor, or aerial (airplane and heli in crops. copter) application methods. 0077. As used herein, sethoxydim is 2-1-(ethoxyimino) I0084 As used herein, plants and vegetation include, but butyl-5-2-(ethylthio)propyl)-3-hydroxy-2-cyclohexen-1- are not limited to, germinant seeds, emerging seedlings, one and possesses the following structure: plants emerging from vegetative propagules, immature veg etation, and established vegetation. I0085. As used herein, agriculturally acceptable salts and refer to salts and esters that exhibit herbicidal activity, O N-" or that are or can be converted in plants, water, or soil to the CH CH referenced herbicide. Exemplary agriculturally acceptable esters are those that are or can be hydrolyzed, oxidized, S OH metabolized, or otherwise converted, e.g., in plants, water, or soil, to the corresponding carboxylic acid which, depending on the pH, may be in the dissociated or undissociated form. ls CH I0086 Exemplary salts include those derived from alkali or alkaline earth metals and those derived from ammonia and 0078. This compound is described in The Pesticide amines. Exemplary cations include sodium, potassium, mag Manual, Fifteenth Edition, 2009. Exemplary uses of sethoxy nesium, and aminium cations of the formula: dim include its use as a herbicide for, e.g., control of annual and perennial grasses in broadleaf crops. 0079. As used herein, tralkoxydim is 2-1-(ethoxyimino) wherein R', R, R and R' each, independently represents propyl)-3-hydroxy-5-(2,4,6-trimethylphenyl)-2-cyclohexen hydrogen or C-C alkyl, C-C alkenyl or C-C alkynyl, 1-one and possesses the following structure: each of which is optionally substituted by one or more hydroxy, C-C alkoxy, C-C alkylthio or phenyl groups, provided that R', R, R and R are sterically compatible. /NCH, Additionally, any two of R', R, R and R together may CH 3 OHH O V represent an aliphatic difunctional moiety containing one to N twelve carbon atoms and up to two oxygen or Sulfur atoms. / Salts can be prepared by treatment with a metal hydroxide, Such as Sodium hydroxide, with an amine, Such as ammonia, CH3 trimethylamine, diethanolamine, 2-methylthiopropylamine, CH 3 O bisallylamine, 2-butoxyethylamine, morpholine, cyclodode cylamine, or benzylamine or with a tetraalkylammonium hydroxide, Such as tetramethylammonium hydroxide or cho 0080. This compound is described in The Pesticide line hydroxide. Manual, Fifteenth Edition, 2009. Exemplary uses of tralkoxydim include its use as a herbicide for, e.g., post I0087 Exemplary esters include those derived from emergence control of annual grass weeds in wheat and barley. C-C alkyl, C-C alkenyl, C-C alkynyl or C7-Caryl Substituted alkyl alcohols, such as methyl alcohol, isopropyl 0081. As used herein, herbicide means a compound, e.g., alcohol, 1-butanol, 2-ethylhexanol, butoxyethanol, methox active ingredient that kills, controls or otherwise adversely ypropanol, allyl alcohol, propargyl alcohol, cyclohexanol or modifies the growth of plants. unsubstituted or substituted benzyl alcohols. Benzyl alcohols 0082. As used herein, a herbicidally effective or vegeta may be substituted with from 1-3 substituents independently tion controlling amount is an amount of active ingredient selected from halogen, C-C alkyl or C-C alkoxy. Esters which causes an adversely modifying effect to the vegetation can be prepared by coupling of the acids with the alcohol e.g., causing deviations from natural development, killing, using any number of Suitable activating agents such as those effecting regulation, causing desiccation, causing retarda used for peptide couplings such as dicyclohexylcarbodiimide tion, and the like. (DCC) or carbonyl diimidazole (CDI); by reacting the acids 0083. As used herein, controlling undesirable vegetation with alkylating agents such as alkylhalides or alkylsulfonates means preventing, reducing, killing, or otherwise adversely in the presence of a base Such as triethylamine or lithium modifying the development of plants and vegetation. carbonate; by reacting the corresponding acid chloride of an Described herein are methods of controlling undesirable veg acid with an appropriate alcohol; by reacting the correspond etation through the application of certain herbicide combina ing acid with an appropriate alcohol in the presence of an acid tions or compositions. Methods of application include, but catalyst or by transesterification. are not limited to applications to the vegetation or locus thereof, e.g., application to the area adjacent to the vegetation, Compositions and Methods as well as preemergence, postemergence, foliar (broadcast, directed, banded, spot, mechanical, over-the-top, or rescue), I0088 Provided herein are herbicidal compositions com and in-water applications (emerged and Submerged vegeta prising a herbicidally effective amount of (a) a compound of tion, broadcast, spot, mechanical, water-injected, granular the formula (I) US 2014/003 1228A1 Jan. 30, 2014

employed, the specific adjuvants and carriers employed, the

(I) soil type, and the like, as well as the amount of chemical applied. These and other factors can be adjusted to promote non-selective or selective herbicidal action. In some embodi ments, the compositions described herein are applied as a post-emergence application, pre-emergence application, or in-water application to flooded paddy rice or water bodies (e.g., ponds, lakes and streams), to relatively immature unde sirable vegetation to achieve the maximum control of weeds. 0094. In some embodiments, the compositions and meth ods provided herein are utilized to control weeds in crops, including but not limited to direct-seeded, water-seeded and transplanted rice, cereals, wheat, barley, oats, rye, Sorghum, corn/maize, Sugarcane, Sunflower, oilseed rape, canola, Sugar or an agriculturally acceptable salt or ester of thereof, and (b) beet, soybean, cotton, pineapple, pastures, grasslands, range an ACCase inhibitor. In certain embodiments, the ACCase lands, fallowland, turf, tree and vine orchards, aquatics, plan inhibitor is clethodim, clodinafop-propargyl, cyhalofop-R- tation crops, vegetables, industrial vegetation management butyl, diclofop-methyl, fenoxaprop-P-ethyl, fluazifop-P-bu tyl, haloxyfop-R-methyl, metamifop, pinoxaden, profoxy (IVM) and rights of way (ROW). dim, quizalofop-P-ethyl, Sethoxydim or tralkoxydim or 0095. In certain embodiments, the compositions and methods provided herein are utilized to control weeds in rice. derivative thereof, e.g., salt, carboxylic acid, carboxylate salt, In certain embodiments, the rice is direct-seeded, water or ester thereof. seeded, or transplanted rice. 0089 Provided herein are also methods of controlling undesirable vegetation comprising contacting the vegetation 0096. The compositions and methods described herein be or the locus thereof, i.e., are adjacent to the vegetation, with or used to control undesirable vegetation in glyphosate-toler applying to the Soil or water to prevent the emergence or ant-, 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase growth of vegetation a herbicidally effective amount of the inhibitor-tolerant-, glufosinate-tolerant-, glutamine Syn thetase inhibitor-tolerant-, dicamba-tolerant-, phenoxy compound of formula (I) and (b) an ACCase inhibitor. In auxin-tolerant-, pyridyloxy auxin-tolerant-, auxin-tolerant-, certain embodiments, the methods employ the compositions auxin transport inhibitor-tolerant-, aryloxyphenoxypropi described herein. onate-tolerant-, cyclohexanedione-tolerant-, phenylpyrazo 0090. Furthermore, in some embodiments, the combina line-tolerant-, acetyl CoA carboxylase (ACCase) inhibitor tion of compound (I) or agriculturally acceptable salt or ester tolerant-, imidazolinone-tolerant-, sulfonylurea-tolerant-, thereof and ACCase inhibitors, or an agriculturally accept pyrimidinylthiobenzoate-tolerant-, triazolopyrimidine-toler able salt or ester thereof exhibits synergism, e.g., the herbi ant-, Sulfonylaminocarbonyltriazolinone-tolerant-, triazol cidal active ingredients are more effective in combination opyrimidine-tolerant-, sulfonylaminocarbonyltriazolinone than when applied individually. Synergism has been defined tolerant-, acetolactate synthase (ALS) or acetohydroxy acid as “an interaction of two or more factors such that the effect synthase (AHAS) inhibitor-tolerant-, 4-hydroxyphenyl when combined is greater than the predicted effect based on pyruvate dioxygenase (HPPD) inhibitor-tolerant-, phytoene the response of each factor applied separately. Senseman, S., desaturase inhibitor-tolerant-, carotenoid biosynthesis inhibi ed. Herbicide Handbook. 9" ed. Lawrence: Weed Science tor-tolerant-, protoporphyrinogen oxidase (PPO) inhibitor Society of America, 2007. In certain embodiments, the com tolerant-, cellulose biosynthesis inhibitor-tolerant-, mitosis positions exhibit synergy as determined by the Colby's equa inhibitor-tolerant-, microtubule inhibitor-tolerant-, very long tion. Colby, S. R. 1967. Calculation of the synergistic and chain fatty acid inhibitor-tolerant-, fatty acid and lipid bio antagonistic response of herbicide combinations. Weeds synthesis inhibitor-tolerant-, photosystem I inhibitor-toler 15:20-22. ant-, photosystem II inhibitor-tolerant-, triazine-tolerant- and 0091. In certain embodiments of the compositions and bromoxynil-tolerant-crops (such as, but not limited to, Soy methods described herein, the compound of formula (I), i.e., bean, cotton, canola/oilseed rape, rice, cereals, corn, Sor the carboxylic acid, is employed. In certain embodiments, a ghum, Sunflower, Sugar beet, Sugarcane, turf, etc.), for carboxylate salt of the compound of formula (I) is employed. example, in conjunction with glyphosate, EPSP synthase In certain embodiments, anaralkyl or alkyl ester is employed. inhibitors, glufosinate, glutamine synthase inhibitors, In certain embodiments, a benzyl, Substituted benzyl, or Ca dicamba, phenoxy auxins, pyridyloxy auxins, synthetic aux alkyl, e.g., n-butyl esteris employed. In certain embodiments, ins, auxin transport inhibitors, aryloxyphenoxypropionates, the benzyl ester is employed. cyclohexanediones, phenylpyrazolines, ACCase inhibitors, 0092. In some embodiments, the compound of formula (I) imidazolinones, Sulfonylureas, pyrimidinylthiobenzoates, or saltorester thereof and ACCase inhibitor are formulated in triazolopyrimidines, Sulfonylaminocarbonyltriazolinones, one composition, tank mixed, applied simultaneously, or ALS or AHAS inhibitors, HPPD inhibitors, phytoene desatu applied sequentially. rase inhibitors, carotenoid biosynthesis inhibitors, PPO 0093. Herbicidal activity is exhibited by the compounds inhibitors, cellulose biosynthesis inhibitors, mitosis inhibi when they are applied directly to the plant or to the locus of tors, microtubule inhibitors, very long chain fatty acid inhibi the plant at any stage of growth. The effect observed depends tors, fatty acid and lipid biosynthesis inhibitors, photosystem upon the plant species to be controlled, the stage of growth of I inhibitors, photosystem II inhibitors, PPO inhibitors, triaz the plant, the application parameters of dilution and spray ines, and bromoxynil The compositions and methods may be drop size, the particle size of solid components, the environ used in controlling undesirable vegetation in crops possess mental conditions at the time of use, the specific compound ing multiple or stacked traits conferring tolerance to multiple US 2014/003 1228A1 Jan. 30, 2014

chemistries and/or inhibitors of multiple modes of action. In ALSPA), Amaranthus species, (pigweeds and amaranths, Some embodiments, the compound of formula (I) or salt or AMASS), Ammannia coccinea Rottb. (redstem, AMMCO). ester thereof and complementary herbicide or salt or ester Commelina benghalensis L. (Benghal dayflower, COMBE), thereofare used in combination with herbicides that are selec Eclipta alba (L.) Hassk. (American false daisy, ECLAL). tive for the crop being treated and which complement the Heteranthera limosa (SW.) Willd./Vahl (ducksalad, HETLI), spectrum of weeds controlled by these compounds at the Heteranthera reniformis R. & P. (roundleaf mudplantain, application rate employed. In some embodiments, the com HETRE), Ipomoea species (morning glories, IPOSS), Ipo positions described herein and other complementary herbi moea hederacea (L.) Jacq. (ivyleaf morning glory, IPOHE), cides are applied at the same time, either as a combination Lindernia dubia (L.) Pennell (low false pimpernel, LIDDU), formulation, tank mix or sequentially. Ludwigia species (LUDSS), Ludwigia linifolia Poir. (south 0097. The compositions and methods may be used in con eastern primrose-willow, LUDLI), Ludwigia Octovalvis trolling undesirable vegetation in crops possessing agro (Jacq.) Raven (longfruited primrose-willow, LUDOC), nomic stress tolerance (including but not limited to drought, Monochoria korsakowii Regel & Maack (monochoria, cold, heat, salt, water, nutrient, fertility, pH), pest tolerance MOOKA), Monochoria vaginalis (Burm. F.) C. Preslex (including but not limited to insects, fungi and pathogens) and Kuhth, (monochoria, MOOVA), Murdannia nudiflora (L.) crop improvement traits (including but not limited to yield; Brenan (doveweed, MUDNU), Polygonum pensylvanicum protein, carbohydrate, or oil content; protein, carbohydrate, L., (Pennsylvania Smartweed, POLPY), Polygonum persi or oil composition; plant stature and plant architecture). caria L. (ladysthumb, POLPE), Polygonum hydropiperoides 0098. The compositions and methods provided herein are Michx. (POLHP. mild smartweed), Rotala indica (Willd.) utilized to control undesirable vegetation. Undesirable veg Koehne (Indian toothcup, ROTIN), Sagittaria species, (ar etation includes, but is not limited to, undesirable vegetation rowhead, SAGSS), Sesbania exaltata (Raf.) Cory/Rydb. Ex that occurs in rice, cereals, wheat, barley, oats, rye, Sorghum, Hill (hemp sesbania, SEBEX), or Sphenoclea zeylanica corn/maize, Sugarcane, Sunflower, oilseed rape, canola, Sugar Gaertn. (gooseweed, SPDZE). beet, soybean, cotton, pineapple, range and pasture, grass 0100. In some embodiments, the methods provided herein lands, fallowland, turf, tree and vine orchards, aquatics, plan are utilized to control undesirable vegetation in cereals. In tation crops, vegetables, industrial vegetation management certain embodiments, the undesirable vegetation is Alopecu (IVM) and rights of way (ROW). rus myosuroides Huds. (blackgrass, ALOMY), Apera spica 0099. In some embodiments, the methods provided herein venti (L.) Beauv. (windgrass, APESV), Avena fatua L. (wild are utilized to control undesirable vegetation in rice. In cer oat, AVEFA), Bromus tectorum L. (downy brome, BROTE), tain embodiments, the undesirable vegetation is Brachiaria Lolium multiflorum Lam. (Italian ryegrass, LOLMU), platyphylla (Groseb.) Nash or Urochloa platyphylla (Nash) Phalaris minor Retz. (littleseed canarygrass, PHAMI), Poa R. D. Webster (broadleaf signalgrass, BRAPP), Digitaria annua L. (annual bluegrass, POANN), Setaria pumila (Poir.) sanguinalis (L.) Scop. (large crabgrass, DIGSA), Echi Roemer & J. A. Schultes (yellow foxtail, SETLU), Setaria nochloa species (ECHSS), Echinochloa crus-galli (L.) P. viridis (L.) Beauv. (green foxtail, SETVI), Amaranthus ret Beauv. (barnyardgrass, ECHCG), Echinochloa crus-pavonis roflexus L. (redroot pigweed, AMARE), Brassica species (Kunth) Schuh. (gulf cockspur, ECHCV), Echinochloa (BRSSS), Chenopodium album L. (common lambsquarters, colonium (L.) LINK (junglerice, ECHCO), Echinochloa CHEAL), Cirsium arvense (L.) Scop. (Canada thistle, Oryzoides (Ard.) Fritsch (early watergrass, ECHOR), Echi CIRAR), Galium aparine L. (catchweedbedstraw, GALAP), nochloa Oryzicola (Vasinger) Vasinger (late watergrass, Kochia scoparia (L.) Schrad. (kochia, KCHSC), Lamium ECHPH), Echinochloa phyllopogon (Stapf) Koso-Pol. (rice purpureum L. (purple deadnettle, LAMPU), Matricaria barnyardgrass, ECHPH), Echinochloa polystachya (Kunth) recutita L. (wild chamomile, MATCH), Matricaria matri Hitchc. (creeping river grass, ECHPO), Ischaemum rugosum carioides (Less.) Porter (pineappleweed, MATMT), Papaver Salisb. (saramollagrass, ISCRU), Leptochloa chinensis (L.) rhoeas L. (common poppy, PAPRH), Polygonum convolvulus Nees (Chinese sprangletop, LEFCH), Leptochloa fascicu L. (wild buckwheat, POLCO), Salsola tragus L. (Russian laris (Lam.) Gray (bearded sprangletop, LEFFA), Leptochloa thistle, SASKR), Sinapis species (SINSS). Sinapis arvensis panicoides (Presl.) Hitchc. (Amazon sprangletop, LEFPA), L. (wild mustard, SINAR) Stellaria media (L.) Vill. (common Oryza species (red and weedy rice, ORYSS), Panicum chickweed, STEME), Veronica persica Poir. (Persian speed dichotomiflorum (L.) Michx. (fall panicum, PANDI), well, VERPE), Viola arvensis Murr. (field violet, VIOAR), or Paspalum dilatatum Poir. (dallisgrass, PASDI), Rottboellia Viola tricolor L. (wild violet, VIOTR). cochinchinensis (Lour.) W. D. Clayton (itchgrass, ROOEX), 0101. In some embodiments, the methods provided herein Cyperus species (CYPSS), Cyperus diformis L. (smallflower are utilized to control undesirable vegetation in range and flatsedge, CYPDI), Cyperus dubius Rottb. (MAPDU), Cype pasture, fallowland, IVM and ROW. In certain embodiments, rus esculentus L. (yellow nutsedge, CYPES), Cyperus iria L. the undesirable vegetation is Ambrosia artemisiifolia L. (rice flatsedge, CYPIR), Cyperus rotundus L. (purple nut (common ragweed, AMBEL), Cassia obtusifolia (sickle pod, sedge, CYPRO), Cyperus serotinus ROTTB./C. B. Clarke CASOB), Centaurea maculosa auct. non Lam. (spottedknap (CYPSE), Eleocharis species (ELOSS), Fimbristylis mili weed, CENMA), Cirsium arvense (L.) Scop. (Canada thistle, acea (L.) Vahl (globe fringerush, FIMMI), Schoenoplectus CIRAR), Convolvulus arvensis L. (field bindweed, CONAR). species (SCPSS), Schoenoplectus juncoides Roxb. (Japanese Daucus carota L. (wild carrot, DAUCA), Euphorbia estula L. bulrush, SCPJU), Bolboschoenus maritimus (L.) Palla or (leafy spurge, EPHES), Lactuca serriola L./Torn. (prickly Schoenoplectus maritimus L. Lye (sea clubrush, SCPMA), lettuce, LACSE), Plantago lanceolata L. (buckhornplantain, Schoenoplectus mucronatus L. (ricefield bulrush, SCPMU), PLALA), Rumex obtusifolius L. (broadleaf dock, RUMOB), Aeschynomene species, (jointvetch, AESSS), Alternanthera Sida spinosa L. (prickly sida, SIDSP). Sinapis arvensis L. philoxeroides (Mart.) Griseb. (alligatorweed, ALRPH), (wild mustard, SINAR), Sonchus arvensis L. (perennial Alisma plantago-aquatica L. (common waterplantain, sowthistle, SONAR), Solidago species (goldenrod, SOOSS), US 2014/003 1228A1 Jan. 30, 2014

Taraxacum officinale G. H. Weber ex Wiggers (dandelion, TROPR), Tridax procumbens L. (coat buttons, TROPR), or TAROF), Trifolium repens L. (white clover, TRFRE), or Xanthium strumarium L. (common cocklebur, XANST). Urtica dioica L. (common nettle, URTDI). 0103) In some embodiments, the methods provided herein 0102. In some embodiments, the methods provided herein are utilized to control undesirable vegetation in turf. In certain are utilized to control undesirable vegetation found in row embodiments, the undesirable vegetation is Bellisperennis L. crops, tree and vine crops and perennial crops. In certain (English daisy, BELPE), Cyperus esculentus L. (yellow nut embodiments, the undesirable vegetation is Alopecurus myo sedge, CYPES), Cyperus species (CYPSS). Digitaria san suroides Huds. (blackgrass, ALOMY), Avena fatua L. (wild guinalis (L.) Scop. (large crabgrass, DIGSA), Diodia virgini oat, AVEFA), Brachiaria decumbens Stapf. or Urochloa ana L. (Virginia buttonweed, DIQVI), Euphorbia species decumbens (Stapf) R. D. Webster (Surinam grass, BRADC), (spurge, EPHSS), Glechoma hederacea L. (ground ivy, Brachiaria brizantha (Hochst. ex A. Rich.) Stapf. or Uro GLEHE), Hydrocotyle umbellata L. (dollarweed, HYDUM), chloa brizantha (Hochst. ex A. Rich.) R. D. (beard grass, Kyllinga species (kyllinga, KYLSS), Lamium amplexicaule BRABR), Brachiaria platyphylla (Groseb.) Nash or Uro L. (henbit, LAMAM), Murdannia nudiflora (L.) Brenan chloa platyphylla (Nash) R. D. Webster (broadleaf signal (doveweed, MUDNU), Oxalis species (woodsorrel, grass, BRAPP), Brachiaria plantaginea (Link) Hitchc. or OXASS), Plantago major L. (broadleaf plantain, PLAMA), Urochloa plantaginea (Link) R. D. Webster (alexandergrass, Plantago lanceolata L. (buckhorn/narrowleaf plantain, BRAPL), Cenchrus echinatus L. (southern sandbar, PLALA), Phyllanthus urinaria L. (chamberbitter, PYLTE), CENEC), Digitaria horizontalis Willd. (Jamaican crabgrass, Rumex obtusifolius L. (broadleaf dock, RUMOB), Stachys DIGHO), Digitaria insularis (L.) Mez, ex Ekman (sourgrass, floridana Shuttlew. (Florida betony, STAFL), Stellaria media TRCIN), Digitaria sanguinalis (L.) Scop. (large crabgrass, (L.) Vill. (common chickweed, STEME), Taraxacum offici DIGSA), Echinochloa crus-galli (L.) P. Beauv. (barn male G. H. Weber ex Wiggers (dandelion, TAROF), Trifolium yardgrass, ECHCG), Echinochloa colonium (L.) Link (un repens L. (white clover, TRFRE), or Viola species (wild vio glerice, ECHCO), Eleusine indica (L.) Gaertn. (goosegrass, let, VIOSS). ELEIN), Lolium multiflorum Lam. (Italian ryegrass, 0104. In some embodiments, the compositions and meth LOLMU), Panicum dichotomiflorum Michx. (fall panicum, ods provided herein are utilized to control undesirable veg PANDI), Panicum miliaceum L. (wild-proso millet, PANMI), etation consisting of grass, broadleaf and sedge weeds. In Setaria faberi Herrm. (giant foxtail, SETFA), Setaria viridis certain embodiments, the compositions and methods pro (L.) Beauv. (green foxtail, SETVI), Sorghum halepense (L.) vided herein are utilized to control undesirable vegetation Pers. (Johnsongrass, SORHA), Sorghum bicolor (L.) Moench including Avena, Brachiaria, Cyperus, Digitaria, Echi ssp. Arundinaceum (shattercane, SORVU), Cyperus esculen nochloa, Fimbristylis, Ipomoea, Ischaemum, Leptochloa, tus L. (yellow nutsedge, CYPES), Cyperus rotundus L. Lolium, Schoenoplectus and Sesbania. (purple nutsedge, CYPRO), Abutilon theophrasti Medik. 0105. In some embodiments, the combination of com (velvetleaf, ABUTH), Amaranthus species (pigweeds and pound (I) or agriculturally acceptable ester or salt thereofand amaranths, AMASS), Ambrosia artemisiifolia L. (common ACCase inhibitors or agriculturally acceptable salt or ester ragweed, AMBEL), Ambrosia psilostachya DC. (western thereof is used to control Avena fatua L. (wild oat, AVEFA). ragweed, AMBPS), Ambrosia trifida L. (giant ragweed, Brachiaria platyphylla (Griseb.) Nash (broadleaf signal AMBTR). Anoda cristata (L.) Schlecht. (spurred anoda, grass, BRAPP), Cyperus diformis L. (smallflower umbrella ANVCR), Asclepias Syriaca L. (common milkweed, sedge, CYPDI), Cyperus esculentus L. (yellow nutsedge, ASCSY), Bidens pilosa L. (hairy beggarticks, BIDPI), Bor CYPES), Cyperus iria L. (rice flatsedge, CYPIR), Cyperus reria species (BOISS), Borreria alata (Aubl.) DC. or Sper rotundus L. (purple nutsedge, CYPRO), Digitaria san macoce alata Aubl. (broadleaf buttonweed, BOILF). Sper guinalis (L.) Scop. (large crabgrass, DIGSA), Echinochloa macose latifolia (broadleaved button weed, BOILF), crus-galli (L.) Beauv. (barnyardgrass, ECHCG), Echi Chenopodium album L. (common lambsquarters, CHEAL), nochloa colona (L.) Link (junglerice, ECHCO), Fimbristylis Cirsium arvense (L.) Scop. (Canada thistle, CIRAR), Com miliacea (L.) Vahl (globe fringerush, FIMMI), Ipomoea hed melina benghalensis L. (tropical spiderwort, COMBE), eracea Jacq. (ivyleaf morning glory, IPOHE), Ischaemum Datura Stramonium L. (jimsonweed, DATST), Daucus rugosum Salisb. (Saramollagrass, ISCRU), Leptochloa chin carota L. (wild carrot, DAUCA), Euphorbia heterophylla L. ensis (L.) Nees (Chinese sprangletop, LEFCH), Lolium mul (wild poinsettia, EPHHL), Euphorbia hirta L. or Chamae tiflorum Lam. (Italian ryegrass, LOLMU), Schoenoplectus Syce hirta (L.) Millsp. (garden spurge, EPHHI), Euphorbia juncoides (Roxb.) Palla (Japanese bulrush, SCPJU), Schoe dentata Michx. (toothed spurge, EPHDE), Erigeron bonar noplectus maritimus (L.) Lye (sea clubrush, SCPMA), Schoe iensis L. or Conyza bonariensis (L.) Cronq. (hairy fleabane, noplectus mucronatus (ricefield bulrush, SCPMU) and Ses ERIBO), Erigeron Canadensis L. or Conyza Canadensis (L.) bania exaltata (hemp sesbania, SEBEX). Cronq. (Canadian fleabane, ERICA), Conyza Sumatrensis 0106 The compounds of formula I or agriculturally (Retz.) E. H. Walker (tall fleabane, ERIFL), Helianthus acceptable salt or ester thereof may be used to control herbi annuus L. (common Sunflower, HELAN), Jacquemontia tam cide resistant or tolerant weeds. The methods employing the nifolia (L.) Griseb. (Smallflower morning glory, IAQTA), Ipo combination of a compound of formula I or agriculturally moea hederacea (L.) Jacq. (ivyleaf morning glory, IPOHE), acceptable Salt or ester thereof and the compositions Ipomoea lacunosa L. (white morning glory, IPOLA), Lactuca described herein may also be employed to control herbicide serriola L./Torn. (prickly lettuce, LACSE), Portulaca olera resistant or tolerant weeds. Exemplary resistant or tolerant cea L. (common purslane, POROL), Richardia species (pus weeds include, but are not limited to, biotypes resistant or ley, RCHSS), Sida species (sida, SIDSS), Sida spinosa L. tolerant to acetolactate synthase (ALS) or acetohydroxy acid (prickly sida, SIDSP). Sinapis arvensis L. (wild mustard, synthase (AHAS) inhibitors, (e.g., imidazolinones, Sulfony SINAR), Solanum ptychanthum Dunal (eastern black night lureas, pyrimidinylthiobenzoates, triazolopyrimidines, Sulfo shade, SOLPT), Tridax procumbens L. (coat buttons, nylaminocarbonyltriazolinones), photosystem II inhibitors US 2014/003 1228A1 Jan. 30, 2014

(e.g., phenylcarbamates, pyridaZinones, triazines, triazino the total amount of active ingredients in the composition. In nes, uracils, amides, , benzothiadiazinones, nitriles, certain embodiments, the composition is applied at an appli phenylpyridazines), acetyl CoA carboxylase (ACCase) cation rate of from about 20 grams active ingredient per inhibitors (e.g., aryloxyphenoxypropionates, cyclohexanedi hectare (gai?ha) to about 260 gai?habased on the total amount ones, phenylpyrazolines), synthetic auxins, (e.g., benzoic of active ingredients in the composition. In some embodi acids, phenoxycarboxylic acids, pyridine carboxylic acids, ments, the methods comprise contacting the undesirable veg quinoline carboxylic acids), auxin transport inhibitors (e.g., etation or locus thereof or applying to the soil or water to phthalamates, semicarbazones), photosystem I inhibitors, prevent the emergence or growth of vegetation with a com (e.g., bipyridyliums), 5-enolpyruvylshikimate-3-phosphate pound of formula (I) or salt or ester thereof and clethodimor (EPSP) synthase inhibitors, (e.g., glyphosate), glutamine salt thereof, e.g., sequentially or simultaneously. In some synthetase inhibitors (e.g., glufosinate, bialafos), microtu embodiments, the clethodim or salt thereof is applied at a rate bule assembly inhibitors, (e.g., benzamides, benzoic acids, from about 17.5 gai/ha to about 280 gai/ha and the compound dinitroanilines, phosphoramidates, ), mitosis inhibi of formula (I) of salt or ester thereof is applied at a rate from tors (e.g., carbamates), very long chain fatty acid (VLCFA) about 2 gae/ha to about 300 gae/ha. In some embodiments, the inhibitors (e.g., acetamides, chloroacetamides, oxyaceta clethodim or salt thereof is applied at a rate from about 70 mides, tetrazolinones), fatty acid and lipid synthesis inhibi gai/ha to about 280 gai/ha and the compound of formula (I) of tors, (e.g., phosphorodithioates, thiocarbamates, benzo salt or ester thereof is applied at a rate from about 8 gae/ha to furanes, chlorocarbonic acids), protoporphyrinogen oxidase about 32 gae/ha. In certain embodiments, the methods utilize (PPO) inhibitors (e.g., diphenylethers, N-phenylphthalim the compound of formula (I), or its benzylor n-butyl ester and ides, oxadiazoles, oxazolidinediones, phenylpyrazoles, pyri clethodim for the control of BRAPP, DIGSA, CYPES and midindiones, thiadiazoles, triazolinones), carotenoid biosyn SCPJU. thesis inhibitors, phytoene desaturase (PDS) inhibitors (e.g., amides, anilidex, furanones, phenoxybutan-amides, pyridi 0109. In certain embodiments of the compositions and aZinones, pyridines), 4-hydroxyphenyl-pyruvate-dioxyge methods described herein, the compound of formula (I) or salt nase (HPPD) inhibitors, (e.g., callistemones, isoxazoles, or ester thereof is used in combination with clodinafop-pro pyrazoles, triketones), cellulose biosynthesis inhibitors (e.g., pargyl or salt, carboxylate salt, carboxylic acid, or ester nitriles, benzamides, quinclorac, triazolocarboxamides), thereof. With regard to the compositions, in some embodi mitosis inhibitors, cellulose biosynthesis inhibitors, herbi ments, the weight ratio of the compound of formula (I) or salt cides with multiple modes-of-action Such as quinclorac, and or ester thereof to clodinafop-propargyl or salt, carboxylate unclassified herbicides such as arylaminopropionic acids, salt, carboxylic acid, or ester thereof is within the range of difenZoquat, endothall, and organoarsenicals. Exemplary from about 1:40 to about 60:1. In certain embodiments, the resistant or tolerant weeds include, but are not limited to, weight ratio of the compound of formula (I) or salt or ester biotypes with resistance or tolerance to multiple herbicides, thereof to clodinafop-propargyl or salt, carboxylate salt, car biotypes with resistance or tolerance to multiple chemical boxylic acid, or ester thereof is within the range of from 1:36 to about 10:1. In certain embodiments, the weight ratio of the classes, biotypes with resistance or tolerance to multiple her compound of formula (I) or saltorester thereofto clodinafop bicide modes-of-action and biotypes with multiple resistance propargyl or salt, carboxylate salt, carboxylic acid, or ester or tolerance mechanisms (e.g., target site resistance or meta thereof is within the range of from 1:6 to about 1:1.5. In bolic resistance). certain embodiments, the compositions provided herein com 0107. In some embodiments, an agriculturally acceptable prise the compound of formula (I) or its benzyl or n-butyl ester or salt of compound (I) is employed. In certain embodi ester and clodinafop-propargyll. With respect to the methods, ments, an agriculturally acceptable ester is employed. In cer in certain embodiments, the methods comprise contacting the tain embodiments, the ester is a C alkyl ester. In certain undesirable vegetation or locus thereof or applying to the soil embodiments, the ester is an n-butyl ester. In certain embodi or water to prevent the emergence or growth of vegetation a ments, the ester is a benzyl ester. In certain embodiments, composition described herein. In some embodiments, the compound (I), which is a carboxylic acid, is employed. composition is applied at an application rate of from about 7 0108. In certain embodiments of the compositions and grams active ingredient per hectare (gai?ha) to about 380 methods described herein, the compound of formula (I) or salt gai/ha based on the total amount of active ingredients in the or ester thereof is used in combination with clethodim or salt composition. In certain embodiments, the composition is or ester thereof. With respect to the compositions, in some applied at an application rate of from about 20 grams active embodiments, the weight ratio of the compound of formula ingredient perhectare (gai/ha) to about 40 gai/habased on the (I) or salt or ester thereof to clethodim or salt or ester thereof total amount of active ingredients in the composition. In some is within the range of from about 1:140 to about 9:1. In certain embodiments, the methods comprise contacting the undesir embodiments, the weight ratio of the compound of formula able vegetation or locus thereof or applying to the Soil or (I) or salt or ester thereof to clethodim or salt or ester thereof water to prevent the emergence or growth of vegetation with is within the range of from about 1:48 to about 3:1. In certain a compound of formula (I) or salt or ester thereof and clod embodiments, the compositions provided herein comprise inafop-propargyl or salt, carboxylate salt, carboxylic acid, or the compound of formula (I) or its benzyl or n-butyl ester and ester thereof, e.g., sequentially or simultaneously. In some clethodim. With respect to the methods, in certain embodi embodiments, the clodinafop-propargyl or salt, carboxylate ments, the methods comprise contacting the undesirable veg salt, carboxylic acid, or ester thereof is applied at a rate from etation or locus thereof or applying to the soil or water to about 5 gai/ha to about 80 gai/ha and the compound of for prevent the emergence or growth of vegetation a composition mula (I) of salt or ester thereof is applied at a rate from about described herein. In some embodiments, the composition is 2 gae/ha to about 300 gae/ha. In some embodiments, the applied at an application rate of from about 20 grams active clodinafop-propargyl or salt, carboxylate salt, carboxylic ingredient per hectare (gai/ha) to about 580 gai/ha based on acid, or ester thereof is applied at a rate from about 15 gai/ha US 2014/003 1228A1 Jan. 30, 2014

to about 30 gai/ha and the compound of formula (I) of salt or 300 gai/ha and the compound of formula (I) of salt or ester ester thereof is applied at a rate from about 5 gae/ha to about thereof is applied at a rate from about 8 g acid equivalent per 10 gae/ha. In one embodiment, the methods utilize the benzyl hectare (gae/ha) to about 42 gae/ha. In certain embodiments, ester of the compound of formula (I) and clodinafop-propar the methods utilize the compound of formula (I), or its benzyl gy1 are used to control LOLMU, KCHSC, PHAMI, APESV ester and cyhalofop-R-butyl. In one embodiment, the meth and ALOMY. ods utilize the compound of formula (I) and cyhalofop-R- 0110. In certain embodiments of the compositions and butyl, wherein the compound of formula (I) is applied at a rate methods described herein, the compound of formula (I) or salt of from about 8.75 g acid equivalent per hectare (gae/ha) to or ester thereof is used in combination with cyhalofop-R- about 42.4 gae?ha, and cyhalofop-R-butyl is applied at a rate butyl or carboxylic acid, carboxylate salt, or ester thereof. of about 90 gai/ha to about 280 gai/ha. In one embodiment, With respect to the compositions, in some embodiments, the the methods utilize the benzyl ester of the compound of weight ratio of the compound of formula (I) or salt or ester formula (I) and cyhalofop-R-butyl, wherein the benzyl ester thereof to cyhalofop-R-butyl carboxylic acid, carboxylate of the compound of formula (I) is applied at a rate of from salt, or ester thereof is within the range of from about 1:155 to about 8.75 g acid equivalent per hectare (gae/ha) to about 35 about 6:1. In certain embodiments, the weight ratio of the gae/ha, and cyhalofop-R-butyl is applied at a rate of about 90 compound of formula (I) or salt or ester thereof to cyhalofop gai/ha to about 300 gai/ha. In certain embodiments, the meth R-butyl or carboxylic acid, carboxylate salt, or ester thereof is ods and compositions utilizing the compound of formula (I) within the range of from 1:32 to about 1:4. In certain embodi or saltorester thereof in combination with cyhalofop-R-butyl ments, the weight ratio of the compound of formula (I) or salt or carboxylic acid, carboxylate salt, or ester thereof are used or ester thereof to cyhalofop-R-butyl or carboxylic acid, car to control ISCRU, IPOHE, ECHOR, SCPSU, LEFCH, boxylate salt, orester thereofis within the range of from about SCPMA, CYPIR, FIMMI, SEBEX, CYPDI, ECHCG, 1:42 to about 10:1. In certain embodiments, the weight ratio ECHSS, or SCPMU. of the compound of formula (I) or salt or ester thereof to 0111. In certain embodiments of the compositions and cyhalofop-R-butyl or carboxylic acid, carboxylate salt, or methods described herein, the compound of formula (I) or salt ester thereof is within the range of from about 1:21 to about or ester thereof is used in combination with diclofop-methyl 5:1. In certain embodiments, the compositions provided or carboxylic acid, carboxylate salt, or ester thereof. With herein comprise the compound of formula (I) or its benzyl regard to the compositions, in Some embodiments, the weight ester and cyhalofop-R-butyl. In one embodiment, the compo ratio of the compound of formula (I) or salt or ester thereof to sition comprises the compound of formula (I) and cyhalofop diclofop-methyl or carboxylic acid, carboxylate salt, or ester R-butyl, wherein the weight ratio of the compound of formula thereof is within the range of from about 1:560 to about 5:1. (I) to cyhalofop-R-butyl is about 1:20.6 to about 1:2.5. In one In certain embodiments, the weight ratio of the compound of embodiment, the composition comprises the benzyl ester of formula (I) or salt or ester thereof to diclofop-methyl or the compound of formula (I) and cyhalofop-R-butyl, wherein carboxylic acid, carboxylate salt, or ester thereof is within the the weight ratio of the benzyl ester of the compound of for range of from 1:255 to about 1:1. In certain embodiments, the mula (I) to cyhalofop-R-butyl is about 1:23 to about 5:1. With weight ratio of the compound of formula (I) or salt or ester respect to the methods, in certain embodiments, the methods thereof to diclofop-methyl or carboxylic acid, carboxylate comprise contacting the undesirable vegetation or locus salt, orester thereof is within the range of from 1:140 to about thereof or applying to the soil or water to prevent the emer 1:9. In certain embodiments, the compositions provided gence or growth of vegetation a composition described herein comprise the compound of formula (I) or its benzyl or herein. In some embodiments, the composition is applied at n-butyl ester and diclofop-methyl. With respect to the meth an application rate of from about 52 grams active ingredient ods, in certain embodiments, the methods comprise contact per hectare (gai?ha) to about 610 gai/ha based on the total ing the undesirable vegetation or locus thereof or applying to amount of active ingredients in the composition. In certain the soil or water to prevent the emergence or growth of veg embodiments, the composition is applied at an application etation a composition described herein. In some embodi rate of from about 99 grams active ingredient per hectare ments, the composition is applied at an application rate of (gai/ha) to about 320 gai/ha based on the total amount of from about 72 grams active ingredient per hectare (gai?ha) to active ingredients in the composition. In some embodiments, about 1,420 gai?habased on the total amount of active ingre the methods comprise contacting the undesirable vegetation dients in the composition. In certain embodiments, the com or locus thereof or applying to the soil or water to prevent the position is applied at an application rate of from about 73 emergence or growth of vegetation with a compound of for grams active ingredient per hectare (gai?ha) to about 610 mula (I) or salt or ester thereof and cyhalofop-R-butyl or gai/ha based on the total amount of active ingredients in the carboxylic acid, carboxylate salt, or ester thereof, e.g., composition. In some embodiments, the methods comprise sequentially or simultaneously. In some embodiments, the contacting the undesirable vegetation or locus thereof or cyhalofop-R-butyl or salt or ester thereof is applied at a rate applying to the Soil or water to prevent the emergence or from about 50 gai?ha to about 310 gai/ha and the compound of growth of vegetation with a compound of formula (I) or salt or formula (I) of salt or ester thereof is applied at a rate from ester thereof and diclofop-methyl or salt or ester thereof, e.g., about 2 gae/ha to about 300 gae/ha. In some embodiments, the sequentially or simultaneously. In some embodiments, the cyhalofop-R-butyl or carboxylic acid, carboxylate salt, or diclofop-methyl or salt or ester thereof is applied at a rate ester thereof is applied at a rate from about 45 gai/ha to about from about 70 gai/ha to about 1,120 gai/ha and the compound 600 gai/ha and the compound of formula (I) of salt or ester of formula (I) of salt or ester thereof is applied at a rate from thereof is applied at a rate from about 4 g acid equivalent per about 2 gae/ha to about 300 gae/ha. In certain embodiments, hectare (gae/ha) to about 85 gae/ha. In some embodiments, the methods utilize the compound of formula (I), or its benzyl the cyhalofop-R-butyl or carboxylic acid, carboxylate salt, or or n-butyl ester and diclofop-methyl are used to control ester thereof is applied at a rate from about 90 gai/ha to about APESV, CYPIR, KCHSC and PHAMI. US 2014/003 1228A1 Jan. 30, 2014

0112. In certain embodiments of the compositions and late salt thereof or other ester is applied at a rate from about methods described herein, the compound of formula (I) or salt 11.5 gai/ha to about 140 gai/ha and the compound of formula or ester thereof is used in combination with fenoxaprop-P- (I) of salt or ester thereof is applied at a rate from about 4.38 ethyl or carboxylic acid or carboxylate salt thereof or other gacid equivalent per hectare (gae/ha) to about 42.4 gae/ha. In ester, and fenoxaprop-P-ethyl can be applied alone or in com certain embodiments, the methods utilize the compound of bination with the safeners isoxadifen-ethyl or mefenpyr-di formula (I), or its benzyl ester and fenoxaprop-P-ethyl. In one ethyl. With regard to the compositions, in some embodi embodiment, the methods utilize the compound of formula (I) ments, the weight ratio of the compound of formula (I) or salt and fenoxaprop-P-ethyl, wherein the compound of formula or ester thereof to fenoxaprop-P-ethyl or carboxylic acid or (I) is applied at a rate of from about 4.38 g acid equivalent per carboxylate salt thereof or other ester is within the range of hectare (gae/ha) to about 42.4 gae?ha, and fenoxaprop-P- from about 1:170 to about 30:1. In certain embodiments, the ethyl is applied at a rate of about 11.5 gai?ha to about 140 weight ratio of the compound of formula (I) or salt or ester gai/ha. In one embodiment, the methods utilize the benzyl thereof to fenoxaprop-P-ethyl or carboxylic acid or carboxy ester of the compound of formula (I) and fenoxaprop-P-ethyl, late salt thereoforother ester is within the range of from 1:16 wherein the benzyl ester of the compound of formula (I) is to about 1.5:1. In certain embodiments, the weight ratio of the applied at a rate of from about 4.38 g acid equivalent per compound of formula (I) or salt or ester thereof to fenox hectare (gae/ha) to about 35 gae/ha, and fenoxaprop-P-ethyl aprop-P-ethyl or carboxylic acid or carboxylate salt thereofor is applied at a rate of about 17.5 gai/ha to about 70 gai/ha. In other ester is within the range of from 1:16 to about 3:1. In certain embodiments, the methods and compositions utilizing certain embodiments, the weight ratio of the compound of the compound of formula (I) or salt or ester thereof in com formula (I) or salt or ester thereof to fenoxaprop-P-ethyl or bination with fenoxaprop-P-ethyl or carboxylic acid or car carboxylic acid or carboxylate salt thereof or other ester is boxylate salt thereoforotherester are used to control CYPIR, within the range of from about 1:32 to about 4:1. In certain ECHOR, FIMMI, SCPJU, CYPES, KCHSC, PHAMI and embodiments, the weight ratio of the compound of formula APESV. (I) or saltorester thereof to fenoxaprop-P-ethyl or carboxylic 0113. In certain embodiments of the compositions and acid or carboxylate salt thereof or other ester is within the methods described herein, the compound of formula (I) or salt range of from about 1:16 to about 2:1. In certain embodi or ester thereof is used in combination with fluazifop-P-butyl ments, the compositions provided herein comprise the com or carboxylic acid or carboxylate salt thereof or other ester. pound of formula (I) or its benzyl ester and fenoxaprop-P- With regard to the compositions, in some embodiments, the ethyl. In one embodiment, the composition comprises the weight ratio of the compound of formula (I) or salt or ester compound of formula (I) and fenoxaprop-P-ethyl, wherein thereof to fluazifop-P-butyl or carboxylic acid or carboxylate the weight ratio of the compound of formula (I) to fenox salt thereof or other ester is within the range of from about aprop-P-ethyl is about 1:14 to about 2:1. In one embodiment, 1:210 to about 3:1. In certain embodiments, the weight ratio the composition comprises the benzyl ester of the compound of the compound of formula (I) or salt or ester thereof to of formula (I) and fenoxaprop-P-ethyl, wherein the weight fluazifop-P-butyl or carboxylic acid or carboxylate salt ratio of the benzyl ester of the compound of formula (I) to thereof or otherester is within the range of from 1:41 to about fenoxaprop-P-ethyl is about 1:16 to about 1:1. With respect to 2.5:1. In certain embodiments, the weight ratio of the com the methods, in certain embodiments, the methods comprise pound of formula (I) or salt or ester thereof to fluazifop-P- contacting the undesirable vegetation or locus thereof or butyl or carboxylic acid or carboxylate salt thereof or other applying to the Soil or water to prevent the emergence or ester is within the range of from 1:41 to about 1:1. In certain growth of vegetation a composition described herein. In some embodiments, the weight ratio of the compound of formula embodiments, the composition is applied at an application (I) or salt or ester thereof to fluazifop-P-butyl or salt or ester rate of from about 13 grams active ingredient per hectare thereof is within the range of from about 1:80 to about 1:1. In (gai/ha) to about 440 gai/ha based on the total amount of certain embodiments, the weight ratio of the compound of active ingredients in the composition. In certain embodi formula (I) or salt or ester thereof to fluazifop-P-butyl or salt ments, the composition is applied at an application rate of orester thereof is within the range of from about 1:36 to about from about 15 grams active ingredient per hectare (gai/ha) to 1:2.5. In certain embodiments, the compositions provided about 90 gai/ha based on the total amount of active ingredi herein comprise the compound of formula (I) or its benzyl ents in the composition. In some embodiments, the methods ester and fluazifop-P-butyl. In one embodiment, the compo comprise contacting the undesirable vegetation or locus sition comprises the compound of formula (I) and fluazifop thereof or applying to the soil or water to prevent the emer P-butyl, wherein the weight ratio of the compound of formula gence or growth of vegetation with a compound of formula (I) (I) to fluazifop-P-butyl is about 1:36 to about 1:2.5. In one or salt or ester thereof and fenoxaprop-P-ethyl or salt or ester embodiment, the composition comprises the benzyl ester of thereof, e.g., sequentially or simultaneously. In some the compound of formula (I) and fluazifop-P-butyl, wherein embodiments, the fenoxaprop-P-ethyl or carboxylic acid or the weight ratio of the benzyl ester of the compound of for carboxylate salt thereof or other ester is applied at a rate from mula (I) to fluazifop-P-butyl is about 1:36 to about 1:5.1. With about 11 gai/ha to about 140 gai/ha and the compound of respect to the methods, in certain embodiments, the methods formula (I) of salt or ester thereof is applied at a rate from comprise contacting the undesirable vegetation or locus about 2 gae/ha to about 300 gae/ha. In some embodiments, the thereof or applying to the soil or water to prevent the emer fenoxaprop-P-ethyl or carboxylic acid or carboxylate salt gence or growth of vegetation a composition described thereoforotherester is applied at a rate from about 5 gai/ha to herein. In some embodiments, the composition is applied at about 300 gai/ha and the compound of formula (I) of salt or an application rate of from about 47 grams active ingredient ester thereof is applied at a rate from about 2 g acid equivalent per hectare (gai?ha) to about 720gai/ha based on the total per hectare (gae/ha) to about 90 gae/ha. In some embodi amount of active ingredients in the composition. In certain ments, the fenoxaprop-P-ethyl or carboxylic acid or carboxy embodiments, the composition is applied at an application US 2014/003 1228A1 Jan. 30, 2014 rate of from about 50 grams active ingredient per hectare prises the compound of formula (I) and haloxyfop-R-methyl, (gai/ha) to about 200 gai/ha based on the total amount of wherein the weight ratio of the compound of formula (I) to active ingredients in the composition. In some embodiments, haloxyfop-R-methyl is about 1:6.2 to about 2.6:1. In one the methods comprise contacting the undesirable vegetation embodiment, the composition comprises the benzyl ester of or locus thereof or applying to the soil or water to prevent the the compound of formula (I) and haloxyfop-R-methyl, emergence or growth of vegetation with a compound of for wherein the weight ratio of the benzyl ester of the compound mula (I) or salt orester thereof and fluazifop-P-butyl or salt or of formula (I) to haloxyfop-R-methyl is about 1:7 to about ester thereof, e.g., sequentially or simultaneously. In some 1.3:1. With respect to the methods, in certain embodiments, embodiments, the fluazifop-P-butyl or carboxylic acid or car the methods comprise contacting the undesirable vegetation boxylate salt thereof or other ester is applied at a rate from or locus thereof or applying to the soil or water to prevent the about 45 gae/ha to about 420 gae/ha and the compound of emergence or growth of vegetation a composition described formula (I) of salt or ester thereof is applied at a rate from herein. In some embodiments, the composition is applied at about 2 gae/ha to about 300 gae/ha. In some embodiments, the an application rate of from about 32 grams active ingredient fluazifop-P-butyl or carboxylic acid or carboxylate salt per hectare (gai/ha) to about 420 gai/ha based on the total thereof or other ester is applied at a rate from about 20 gai?ha amount of active ingredients in the composition. In certain to about 400 gai/ha and the compound of formula (I) of salt or embodiments, the composition is applied at an application ester thereof is applied at a rate from about 2 g acid equivalent rate of from about 10 grams active ingredient per hectare per hectare (gae/ha) to about 70 gae/ha. In some embodi (gai?ha) to about 60 gai?habased on the total amount of active ments, the fluazifop-P-butyl or carboxylic acid or carboxylate ingredients in the composition. In some embodiments, the salt thereof or other ester is applied at a rate from about 45 methods comprise contacting the undesirable vegetation or gai?ha to about 180 gai/ha and the compound of formula (I) of locus thereof or applying to the soil or water to prevent the salt or ester thereof is applied at a rate from about 4.38 g acid emergence or growth of vegetation with a compound of for equivalent per hectare (gae/ha) to about 35 gae/ha. In certain mula (I) or salt or ester thereof and haloxyfop-R-methyl or embodiments, the methods utilize the compound of formula carboxylic acid or carboxylate Salt thereof or otherester, e.g., (I), or its benzyl ester and fluazifop-P-butyl. In one embodi sequentially or simultaneously. In some embodiments, the ment, the methods utilize the compound of formula (I) and haloxyfop-R-methyl or carboxylic acid or carboxylate salt fluazifop-P-butyl, wherein the compound of formula (I) is thereof or other ester is applied at a rate from about 6.75 applied at a rate of from about 4.38 g acid equivalent per gae/ha to about 120 gae/ha and the compound of formula (I) hectare (gae/ha) to about 35 gae/ha, and fluazifop-P-butyl is of salt or ester thereof is applied at a rate from about 2 gae?ha applied at a rate of about 45 gai/ha to about 180 gai/ha. In one to about 300 gae/ha. In some embodiments, the haloxyfop embodiment, the methods utilize the benzyl ester of the com R-methyl or carboxylic acid or carboxylate salt thereof or pound of formula (I) and fluazifop-P-butyl, wherein the ben otherester is applied at a rate from about 3 gai/ha to about 140 Zyl ester of the compound of formula (I) is applied at a rate of gai/ha and the compound of formula (I) of saltorester thereof from about 4.38 g acid equivalent per hectare (gae/ha) to is applied at a rate from about 2 g acid equivalent per hectare about 8.75 gae/ha, and fluazifop-P-butyl is applied at a rate of (gae/ha) to about 45 gae/ha. In some embodiments, the about 45 gai/ha to about 180 gai/ha. In certain embodiments, haloxyfop-R-methyl or carboxylic acid or carboxylate salt the methods and compositions utilizing the compound of thereof or other ester is applied at a rate from about 6.75 formula (I) or salt or ester thereof in combination with flu gai/ha to about 70 gai/ha and the compound of formula (I) of azifop-P-butyl or carboxylic acid or carboxylate salt thereof salt or ester thereof is applied at a rate from about 4.38 g acid or other ester are used to control IPOHE, ECHOR, or equivalent per hectare (gae/ha) to about 17.5 gae/ha. In cer CYPRO. tain embodiments, the methods utilize the compound of for 0114. In certain embodiments of the compositions and mula (I), or its benzyl or n-butyl ester and haloxyfop-R- methods described herein, the compound of formula (I) or salt methyl. In one embodiment, the methods utilize the or ester thereof is used in combination with haloxyfop-R- compound of formula (I) and haloxyfop-R-methyl, wherein methyl or carboxylic acid or carboxylate salt thereof or other the compound of formula (I) is applied at a rate of from about ester. With regard to the compositions, in some embodiments, 4.38 g acid equivalent per hectare (gae/ha) to about 35 gae/ha, the weight ratio of the compound of formula (I) or saltorester and haloxyfop-R-methyl is applied at a rate of about 6.75 thereof to haloxyfop-R-methyl or carboxylic acid or carboxy gai/ha to about 70 gai/ha. In one embodiment, the methods late salt thereoforotheresteris within the range of from about utilize the benzyl ester of the compound of formula (I) and 1:45 to about 10:1. In certain embodiments, the weight ratio haloxyfop-R-methyl, wherein the benzyl ester of the com of the compound of formula (I) or salt or ester thereof to pound of formula (I) is applied at a rate of from about 4.38g haloxyfop-R-methyl or carboxylic acid or carboxylate salt acid equivalent per hectare (gae/ha) to about 17.5 gae/ha, and thereof or other ester is within the range of from 1:6 to about haloxyfop-R-methyl is applied at a rate of about 6.75 gai?ha to 2.5:1. In certain embodiments, the weight ratio of the com about 27 gai/ha. In certain embodiments, the methods and pound of formula (I) or salt or ester thereof to haloxyfop-R- compositions utilizing the compound of formula (I) or salt or methyl or carboxylic acid or carboxylate salt thereof or other ester thereof in combination with haloxyfop-R-methyl or car ester is within the range of from about 1:15 to about 6:1. In boxylic acid or carboxylate salt thereoforotherester are used certain embodiments, the weight ratio of the compound of to control ECHCO, IPOHE, SCPJU, BRAPP, or CYPRO. formula (I) or salt or ester thereof to haloxyfop-R-methyl or 0.115. In certain embodiments of the compositions and carboxylic acid or carboxylate salt thereof or other ester is methods described herein, the compound of formula (I) or salt within the range of from about 1:7 to about 2.6:1. In certain or ester thereof is used in combination with metamifop or salt embodiments, the compositions provided herein comprise or ester thereof. With regard to the compositions, in some the compound of formula (I) or its benzyl ester and haloxy embodiments, the weight ratio of the compound of formula fop-R-methyl. In one embodiment, the composition com (I) or salt or ester thereof to metamifop or salt orester thereof US 2014/003 1228A1 Jan. 30, 2014

is within the range of from about 1:150 to about 6:1. In certain certain embodiments, the methods and compositions utilizing embodiments, the weight ratio of the compound of formula the compound of formula (I) or salt or ester thereof in com (I) or salt or ester thereofto metamifop or salt orester thereof bination with metamifop or salt or ester thereof are used to is within the range of from 1:34 to about 10:1. In certain control IPOHE, ECHCG, ECHOR, IPOHE, FIMMI, embodiments, the weight ratio of the compound of formula SCPMA, or SCPJU. (I) or salt or ester thereofto metamifop or salt orester thereof 0116. In certain embodiments of the compositions and is within the range of from 1:34 to about 1:2. In certain methods described herein, the compound of formula (I) or salt embodiments, the weight ratio of the compound of formula or ester thereof is used in combination with pinoxaden or salt (I) or salt or ester thereofto metamifop or salt orester thereof or ester thereof. With regard to the compositions, in some is within the range of from about 1:60 to about 1:1. In certain embodiments, the weight ratio of the compound of formula embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to pinoxaden or salt or ester thereof (I) or salt or ester thereofto metamifop or salt orester thereof is within the range of from about 1:30 to about 150: 1. In is within the range of from about 1:30 to about 1:2.1. In certain embodiments, the weight ratio of the compound of certain embodiments, the compositions provided hereincom formula (I) or saltorester thereof to pinoxaden or salt or ester prise the compound of formula (I) or its benzyl ester and thereof is within the range of from 1:27 to about 25:1. In metamifop. In one embodiment, the composition comprises certain embodiments, the weight ratio of the compound of the compound of formula (I) and metamifop, wherein the formula (I) or saltorester thereof to pinoxaden or salt or ester weight ratio of the compound of formula (I) to metamifop is thereof is within the range of from 1:12 to about 2:1. In certain about 1:30 to about 1:2.1. In one embodiment, the composi embodiments, the compositions comprise the compound of tion comprises the benzyl ester of the compound of formula formula (I) or its benzyl or n-butyl ester and pinoxaden. With (I) and metamifop, wherein the weight ratio of the benzyl respect to the methods, in certain embodiments, the methods ester of the compound of formula (I) to metamifop is about comprise contacting the undesirable vegetation or locus 1:30 to about 1:15. With respect to the methods, in certain thereof or applying to the soil or water to prevent the emer embodiments, the methods comprise contacting the undesir gence or growth of vegetation a composition described able vegetation or locus thereof or applying to the Soil or herein. In some embodiments, the composition is applied at water to prevent the emergence or growth of vegetation a an application rate of from about 4 grams active ingredient composition described herein. In some embodiments, the per hectare (gai?ha) to about 360 gai/ha based on the total composition is applied at an application rate of from about 52 amount of active ingredients in the composition. In certain grams active ingredient per hectare (gai?ha) to about 600 embodiments, the composition is applied at an application gai/ha based on the total amount of active ingredients in the rate of from about 8 grams active ingredient per hectare composition. In certain embodiments, the composition is (gai?ha) to about 110 gai/ha based on the total amount of applied at an application rate of from about 40 grams active active ingredients in the composition. In some embodiments, ingredient per hectare (gai/ha) to about 170 gai/ha based on the methods comprise contacting the undesirable vegetation the total amount of active ingredients in the composition. In or locus thereof or applying to the soil or water to prevent the Some embodiments, the methods comprise contacting the emergence or growth of vegetation with a compound of for undesirable vegetation or locus thereof or applying to the soil mula (I) or salt or ester thereof and pinoxaden or salt thereof, or water to prevent the emergence or growth of vegetation e.g., sequentially or simultaneously. In some embodiments, with a compound of formula (I) or salt or ester thereof and the pinoxaden or salt or ester thereof is applied at a rate from metamifop or salt orester thereof, e.g., sequentially or simul about 2 gai/ha to about 60 gai/ha and the compound of for taneously. In some embodiments, the metamifop or salt or mula (I) of salt or ester thereof is applied at a rate from about ester thereof is applied at a rate from about 50 gai/ha to about 2 gae/ha to about 300 gae/ha. In some embodiments, the 300 gai/ha and the compound of formula (I) of salt or ester pinoxaden or salt or ester thereof is applied at a rate from thereof is applied at a rate from about 2 gae/ha to about 300 about 15 gai/ha to about 60 gai/ha and the compound of gae/ha. In some embodiments, the metamifop or salt or ester formula (I) of salt or ester thereof is applied at a rate from thereof is applied at a rate from about 30 gai/ha to about 300 about 5 gae?ha to about 32 gae/ha. In certain embodiments, gai/ha and the compound of formula (I) of saltorester thereof the methods utilize the compound of formula (I) or its benzyl is applied at a rate from about 2 g acid equivalent per hectare or n-butyl ester and pinoxaden for the control of ECHCO, (gae/ha) to about 70 gae/ha. In some embodiments, the IPOHE, KCHSC, PHAMI and SCPJU. metamifop or salt or ester thereof is applied at a rate from 0117. In certain embodiments of the compositions and about 75 gai/ha to about 150 gai/ha and the compound of methods described herein, the compound of formula (I) or salt formula (I) of salt or ester thereof is applied at a rate from or ester thereof is used in combination with profoxydim or about 4.38 g acid equivalent per hectare (gae/ha) to about 35 saltorester thereof. With regard to the compositions, in some gae/ha. In certain embodiments, the methods utilize the com embodiments, the weight ratio of the compound of formula pound of formula (I), or its benzyl ester and metamifop. In (I) or salt or ester thereof to profoxydimor saltorester thereof one embodiment, the methods utilize the compound of for is within the range of from about 1:70 to about 29:1. In certain mula (I) and metamifop, wherein the compound of formula embodiments, the weight ratio of the compound of formula (I) is applied at a rate of from about 4.38 gacid equivalent per (I) or salt or ester thereof to profoxydimor saltorester thereof hectare (gae/ha) to about 35 gae/ha, and metamifop is applied is within the range of from 1:8 to about 2:1. In certain embodi at a rate of about 75 gai/ha to about 150 gai/ha. In one ments, the weight ratio of the compound of formula (I) or salt embodiment, the methods utilize the benzyl ester of the com or ester thereof to profoxydim or saltorester thereof is within pound of formula (I) and metamifop, wherein the benzyl ester the range of from about 1:10 to about 3:1. In certain embodi of the compound of formula (I) is applied at a rate of about ments, the weight ratio of the compound of formula (I) or salt 4.38 g acid equivalent per hectare (gae/ha), and metamifop is or ester thereof to profoxydim or saltorester thereof is within applied at a rate of about 75 gai/ha to about 150 gai/ha. In the range of from about 1:23 to about 3:1. In certain embodi US 2014/003 1228A1 Jan. 30, 2014 ments, the weight ratio of the compound of formula (I) or salt thereof to quizalofop-P-ethyl or carboxylic acid or carboxy or ester thereof to profoxydim or saltorester thereof is within late salt thereoforotheresteris within the range of from about the range of from about 1:5 to about 1.4:1. In certain embodi 1:100 to about 12:1. In certain embodiments, the weight ratio ments, the compositions provided herein comprise the com of the compound of formula (I) or salt or ester thereof to pound of formula (I) or its benzyl ester and profoxydim. In quizalofop-P-ethyl or carboxylic acid or carboxylate salt one embodiment, the composition comprises the compound thereof or other ester is within the range of from 1:8 to about of formula (I) and profoxydim, wherein the weight ratio of the 19:1. In certain embodiments, the weight ratio of the com compound of formula (I) to profoxydim is about 1:3. In one pound of formula (I) or salt or ester thereof to quizalofop-P- embodiment, the composition comprises the benzyl ester of ethyl or carboxylic acid or carboxylate salt thereof or other the compound of formula (I) and profoxydim, wherein the ester is within the range of from 1:6 to about 1:1. In certain weight ratio of the benzyl ester of the compound of formula embodiments, the weight ratio of the compound of formula (I) to profoxydim is about 1:5 to about 1.4:1. With respect to (I) or salt or ester thereof to quizalofop-P-ethyl or carboxylic the methods, in certain embodiments, the methods comprise acid or carboxylate salt thereof or other ester is within the contacting the undesirable vegetation or locus thereof or range of from about 1:12 to about 10:1. In certain embodi applying to the Soil or water to prevent the emergence or ments, the weight ratio of the compound of formula (I) or salt growth of vegetation a composition described herein. In some or ester thereof to quizalofop-P-ethyl or carboxylic acid or embodiments, the composition is applied at an application carboxylate salt thereof or other ester is within the range of rate of from about 15 grams active ingredient per hectare from about 1:6 to about 5:1. In certain embodiments, the (gai/ha) to about 500 gai/ha based on the total amount of compositions provided herein comprise the compound of active ingredients in the composition. In certain embodi formula (I) or its benzyl ester and quizalofop-P-ethyl. In one ments, the composition is applied at an application rate of embodiment, the composition comprises the compound of from about 16 grams active ingredient per hectare (gai/ha) to formula (I) and quizalofop-P-ethyl, wherein the weight ratio about 50 gai/ha based on the total amount of active ingredi of the compound of formula (I) to quizalofop-P-ethyl is about ents in the composition. In some embodiments, the methods 1:6 to about 5:1. In one embodiment, the composition com comprise contacting the undesirable vegetation or locus prises the benzyl ester of the compound of formula (I) and thereof or applying to the soil or water to prevent the emer quizalofop-P-ethyl, wherein the weight ratio of the benzyl gence or growth of vegetation with a compound of formula (I) ester of the compound of formula (I) to quizalofop-P-ethyl is or saltorester thereof and profoxydimor saltorester thereof, about 1:6 to about 5:1. With respect to the methods, in certain e.g., sequentially or simultaneously. In some embodiments, embodiments, the methods comprise contacting the undesir the profoxydimor saltorester thereof is applied at a rate from able vegetation or locus thereof or applying to the Soil or about 12 gai/ha to about 200 gai/ha and the compound of water to prevent the emergence or growth of vegetation a formula (I) of salt or ester thereof is applied at a rate from composition described herein. In some embodiments, the about 2 gae/ha to about 300 gae/ha. In some embodiments, the composition is applied at an application rate of from about 6 profoxydim or salt or ester thereof is applied at a rate from grams active ingredient per hectare (gai?ha) to about 400 about 4 gai/ha to about 140 gai/ha and the compound of gai/ha based on the total amount of active ingredients in the formula (I) of salt or ester thereof is applied at a rate from composition. In certain embodiments, the composition is about 2 g acid equivalent per hectare (gae/ha) to about 45 applied at an application rate of from about 8 grams active gae/ha. In some embodiments, the profoxydim or salt or ester ingredient perhectare (gai/ha) to about 50 gai/habased on the thereof is applied at a rate from about 12.5 gai/ha to about 25 total amount of active ingredients in the composition. In some gai/ha and the compound of formula (I) of saltorester thereof embodiments, the methods comprise contacting the undesir is applied at a rate from about 4.38 g acid equivalent per able vegetation or locus thereof or applying to the Soil or hectare (gae/ha) to about 17.5 gae/ha. In certain embodi water to prevent the emergence or growth of vegetation with ments, the methods utilize the compound of formula (I), or its a compound of formula (I) or salt or ester thereof and quiza benzyl or n-butyl ester and profoxydim. In one embodiment, lofop-P-ethyl or carboxylic acid or carboxylate salt thereofor the methods utilize the compound of formula (I) and profoxy other ester, e.g., sequentially or simultaneously. In some dim, wherein the compound of formula (I) is applied at a rate embodiments, the quizalofop-P-ethyl or carboxylic acid or of about 4.38 g acid equivalent per hectare (gae/ha), and carboxylate salt thereof or other ester is applied at a rate from profoxydim is applied at a rate of about 12.5 gai/ha. In one about 4 gai/ha to about 100 gae/ha and the compound of embodiment, the methods utilize the benzyl ester of the com formula (I) of salt or ester thereof is applied at a rate from pound of formula (I) and profoxydim, wherein the benzyl about 2 gae/ha to about 300 gae/ha. In some embodiments, the ester of the compound of formula (I) is applied at a rate of quizalofop-P- or carboxylic acid or carboxylate salt thereofor from about 4.38 g acid equivalent per hectare (gae/ha) to other ester is applied at a rate from about 2 gai?ha to about 60 about 17.5 gae/ha, and profoxydim is applied at a rate of about gai/ha and the compound of formula (I) of saltorester thereof 12.5 gai/ha to about 25 gai/ha. In certain embodiments, the is applied at a rate from about 2 g acid equivalent per hectare methods and compositions utilizing the compound of formula (gae/ha) to about 70 gae/ha. In some embodiments, the quiza (I) or salt or ester thereof in combination with profoxydimor lofop-P-ethyl or carboxylic acid or carboxylate salt thereofor salt or ester thereof are used to control ECHCO, ECHCO, other ester is applied at a rate from about 3.56 gai/ha to about SCPU or LEFCH. 30 gai/ha and the compound of formula (I) of salt or ester 0118. In certain embodiments of the compositions and thereof is applied at a rate from about 3.75 g acid equivalent methods described herein, the compound of formula (I) or salt per hectare (gae/ha) to about 35 gae/ha. In certain embodi or ester thereof is used in combination with quizalofop-P- ments, the methods utilize the compound of formula (I), or its ethyl or carboxylic acid or carboxylate salt thereof or other benzyl ester and quizalofop-P-ethyl. In one embodiment, the ester. With regard to the compositions, in some embodiments, methods utilize the compound of formula (I) and quizalofop the weight ratio of the compound of formula (I) or saltorester P-ethyl, wherein the compound of formula (I) is applied at a US 2014/003 1228A1 Jan. 30, 2014

rate of from about 3.75 g acid equivalent per hectare (gae/ha) thereof is applied at a rate from about 30 gai/ha to about 600 to about 35 gae/ha, and quizalofop-P-ethyl is applied at a rate gai/ha and the compound of formula (I) of saltorester thereof of about 3.56 gai/ha to about 30 gai/ha. In one embodiment, is applied at a rate from about 2 g acid equivalent per hectare the methods utilize the benzyl ester of the compound of (gae/ha) to about 45 gae/ha. In some embodiments, the set formula (I) and quizalofop-P-ethyl, wherein the benzyl ester hoxydimor saltorester thereof is applied at a rate from about of the compound of formula (I) is applied at a rate of from 67.5 gai/ha to about 270 gai/ha and the compound of formula about 3.75g acid equivalent per hectare (gae/ha) to about 17.5 (I) of salt or ester thereof is applied at a rate from about 4.38 gae/ha, and quizalofop-P-ethyl is applied at a rate of about gacid equivalent per hectare (gae/ha) to about 17.5 gae/ha. In 3.56 gai/ha to about 30 gai/ha. In certain embodiments, the certain embodiments, the methods utilize the compound of methods and compositions utilizing the compound of formula formula (I), or its benzyl ester and sethoxydim. In one (I) or salt or ester thereof in combination with quizalofop-P- embodiment, the methods utilize the compound of formula (I) ethyl or carboxylic acid or carboxylate salt thereof or other and Sethoxydim, wherein the compound of formula (I) is ester are used to control IPOHE, ECHOR, CYPRO, ECHCG, applied at a rate of from about 4.38 g acid equivalent per AVEFA, LOLMU. hectare (gae/ha) to about 17.5 gae?ha, and Sethoxydim is 0119. In certain embodiments of the compositions and applied at a rate of about 67.5 gai/ha to about 270 gai/ha. In methods described herein, the compound of formula (I) or salt one embodiment, the methods utilize the benzyl ester of the orester thereofis used in combination with sethoxydimor salt compound of formula (I) and sethoxydim, wherein the benzyl or ester thereof. With regard to the compositions, in some ester of the compound of formula (I) is applied at a rate of embodiments, the weight ratio of the compound of formula from about 4.38 g acid equivalent per hectare (gae/ha) to (I) or saltorester thereof to sethoxydimor salt or ester thereof about 8.75 gae/ha, and sethoxydim is applied at a rate of about is within the range of from about 1:70 to about 29:1. In certain 135 gai/ha. In certain embodiments, the methods and com embodiments, the weight ratio of the compound of formula positions utilizing the compound of formula (I) or Saltorester (I) or saltorester thereof to sethoxydimor salt or ester thereof thereof in combination with sethoxydim or salt or ester is within the range of from 1:8 to about 2:1. I In certain thereofare used to control CYPES, CYPDI, CYPIR, SCPJU, embodiments, the weight ratio of the compound of formula LEFCH, FIMMI, or ECHCG. (I) or saltorester thereof to sethoxydimor salt or ester thereof I0120 In certain embodiments of the compositions and is within the range of from about 1:61 to about 1:2. In certain methods described herein, the compound of formula (I) or salt embodiments, the weight ratio of the compound of formula or ester thereof is used in combination with tralkoxydim or (I) or saltorester thereofto sethoxydimor saltoresterthereof saltorester thereof. With regard to the compositions, in some is within the range of from about 1:120 to about 1:3. In certain embodiments, the weight ratio of the compound of formula embodiments, the weight ratio of the compound of formula (I) or saltorester thereof to tralkoxydimor saltorester thereof (I) or saltorester thereof to sethoxydimor salt or ester thereof is within the range of from about 1:38 to about 60:1. In certain is within the range of from about 1:54 to about 1:7.7. In embodiments, the weight ratio of the compound of formula certain embodiments, the compositions provided hereincom (I) or saltorester thereof to tralkoxydimor saltorester thereof prise the compound of formula (I) or its benzyl ester and is within the range of from 1:23 to about 10:1. In certain Sethoxydim. In one embodiment, the composition comprises embodiments, the weight ratio of the compound of formula the compound of formula (I) and sethoxydim, wherein the (I) or saltorester thereof to tralkoxydimor saltorester thereof weight ratio of the compound of formula (I) to sethoxydim is is within the range of from 1:40 to about 1:2. In certain about 1:54 to about 1:7.7. In one embodiment, the composi embodiments, the compositions comprise the compound of tion comprises the benzyl ester of the compound of formula formula (I) or its benzyl or n-butyl ester and tralkoxydim. (I) and sethoxydim, wherein the weight ratio of the benzyl With respect to the methods, in certain embodiments, the ester of the compound of formula (I) to sethoxydim is about methods comprise contacting the undesirable vegetation or 1:27 to about 1:15.4. With respect to the methods, in certain locus thereof or applying to the soil or water to prevent the embodiments, the methods comprise contacting the undesir emergence or growth of vegetation a composition described able vegetation or locus thereof or applying to the Soil or herein. In some embodiments, the composition is applied at water to prevent the emergence or growth of vegetation a an application rate of from about 7 grams active ingredient composition described herein. In some embodiments, the per hectare (gai?ha) to about 375 gai/ha based on the total composition is applied at an application rate of from about 55 amount of active ingredients in the composition. In certain grams active ingredient per hectare (gai/ha) to about 825 embodiments, the composition is applied at an application gai/ha based on the total amount of active ingredients in the rate of from about 8 grams active ingredient per hectare composition. In certain embodiments, the composition is (gai/ha) to about 100 gai/ha based on the total amount of applied at an application rate of from about 55 grams active active ingredients in the composition. In some embodiments, ingredient per hectare (gai/ha) to about 300 gai/ha based on the methods comprise contacting the undesirable vegetation the total amount of active ingredients in the composition. In or locus thereof or applying to the soil or water to prevent the Some embodiments, the methods comprise contacting the emergence or growth of vegetation with a compound of for undesirable vegetation or locus thereof or applying to the soil mula (I) or salt or ester thereof and tralkoxydim or salt or water to prevent the emergence or growth of vegetation thereof, e.g., sequentially or simultaneously. In some with a compound of formula (I) or salt or ester thereof and embodiments, the tralkoxydim or salt or ester thereof is Sethoxydimor saltorester thereof, e.g., sequentially or simul applied at a rate from about 5 gai/ha to about 75 gai/ha and the taneously. In some embodiments, the Sethoxydim or salt or compound of formula (I) of salt or ester thereof is applied at ester thereof is applied at a rate from about 50 gai/ha to about a rate from about 2 gae/ha to about 300 gae/ha. In certain 525 gai/ha and the compound of formula (I) of salt or ester embodiments, the methods utilize the compound of formula thereof is applied at a rate from about 2 gae/ha to about 300 (I) or its benzyl or n-butyl ester and tralkoxydim are used to gae/ha. In some embodiments, the Sethoxydim or salt or ester control AVEFA, CYPIR, KCHSC and LOLMU. US 2014/003 1228A1 Jan. 30, 2014

0121 The components of the mixtures described herein flupoxam, flupropacil, flupropanate, flupyrsulfuron, fluri can be applied either separately or as part of a multipart done, fluorochloridone, fluoroxypyr, fluoroxypyr-meptyl, herbicidal system. flurtamone, fluthiacet, , foramsulfuron, fosamine, 0122) The mixtures described herein can be applied in fumiclorac, furyloxyfen, glufosinate, glufosinate-ammo conjunction with one or more other herbicides to control a nium, glufosinate-P-ammonium, glyphosate salts and esters, wider variety of undesirable vegetation. When used in con halauXifen, halauXifen-methyl, halosafen, halosulfuron-me junction with other herbicides, the composition can be for thyl, haloxydine, hexachloroacetone, hexaflurate, hexazi mulated with the other herbicide or herbicides, tank mixed none, imazamethabenZ, imaZamox, , , with the other herbicide or herbicides or applied sequentially imaZaquin, imaZoSulfuron, imazethapyr, indanofan, indazi with the other herbicide or herbicides. Some of the herbicides flam, iodobonil, iodomethane, iodosulfuron, iodosulfuron that can be employed in conjunction with the compositions ethyl-Sodium, iofensulfuron, ioxynil, ipazine, ipfencarba and methods described herein include, but are not limited to: Zone, iprymidam, isocarbamid, isocil, isomethiozin, 4-CPA: 4-CPB: 4-CPP; 2,4-D; 2,4-D choline salt, 2,4-D isonoruron, isopolinate, isopropalin, isoproturon, isouron, esters and amines, 2,4-DB; 3,4-DA, 3,4-DB; 2,4-DEB; 2,4- isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, karbuti DEP: 3,4-DP: 2,3,6-TBA; 2,4,5-T; 2,4,5-TB; , aci late, ketospiradox, , lenacil, , MAA, MAMA, fluorfen, , acrolein, , allidochlor, alloxydim, MCPA esters and amines, MCPA-thioethyl, MCPB, meco allyl alcohol, alorac, ametridione, ametryn, amibuzin, ami prop, -P, medinoterb, mefenacet, mefluidide, meso carbazone, amidosulfuron, , aminopy prazine, mesosulfuron, , metam, metamitron, ralid, amiprofoS-methyl, amitrole, ammonium Sulfamate, metaZachlor, metazosulfuron, metflurazon, methabenzthia anilofos, anisuron, , atraton, , azafenidin, Zuron, methalpropalin, , methiobencarb, methio azimsulfuron, aziprotryne, barban, BCPC, beflubutamid, Zolin, methiuron, methometon, methoprotryne, methyl bro benazolin, bencarbazone, , benfuresate, bensulfu mide, methyl isothiocyanate, methyldymron, metobenzuron, ron-methyl, , benthiocarb, -Sodium, ben Zadox, benzfendizone, benzipram, benzobicyclon, ben metobromuron, , metoSulam, metoXuron, Zofenap, benzofluor, benzoylprop, benzthiazuron, , , metSulfuron, metSulfuron-methyl, molinate, bicyclopyrone, , bilanafos, bispyribac-Sodium, borax, monalide, monisouron, monochloroacetic acid, monolinu bromacil, bromobonil, bromobutide, bromofenoxim, bro ron, monuron, morfamquat, MSMA, naproanilide, napropa moxynil, brompyrazon, , , butamifos, mide, naptalam, neburon, nicosulfuron, nipyraclofen, nitra butenachlor, buthidazole, buthiuron, butralin, butroxydim, lin, , nitrofluorfen, norflurazon, noruron, OCH, buturon, butylate, , cafenstrole, calcium chlo orbencarb, ortho-dichlorobenzene, orthosulfamuron, oryza rate, calcium cyanamide, cambendichlor, carbasulam, carbe lin, oxadiargyl, oxadiazon, oxapyrazon, oxasulfuron, oxazi tamide, carboxazole chlorprocarb, carfentraZone-ethyl, clomefone, oxyfluorfen, paraflufen-ethyl, parafluoron, CDEA, CEPC, chlomethoxyfen, , chloranocryl, , pebulate, pelargonic acid, , penoXSu chlorazifop, chlorazine, chlorbromuron, chlorbufam, chlore lam, pentachlorophenol, pentanochlor, pentoxazone, perflui turon, chlorfenac, chlorfenprop, chlorflurazole, chlorflure done, pethoxamid, phenisopham, phenmedipham, phenme nol, chloridazon, chlorimuron, chlornitrofen, chloropon, dipham-ethyl, phenobenzuron, phenylmercury acetate, chlorotoluron, , chloroxynil, chlorpropham, , picolinafen, piperophos, potassium arsenite, potas chlorsulfuron, chlorthal, chlorthiamid, cinidon-ethyl, cinm sium azide, potassium cyanate, pretilachlor, primisulfuron ethylin, cinosulfuron, cisanilide, cliodinate, clofop, cloma methyl, procyazine, prodiamine, profluaZol, profluralin, pro Zone, clomeprop, cloprop, cloproxydim, , cloran glinazine, prohexadione-calcium, , prometryn, Sulam-methyl, CMA, copper sulfate, CPMF, CPPC, pronamide, , , propaquizafop, propazine, credazine, cresol, cumyluron, cyanatryn, , cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, propham, propisochlor, propoxycarbazone, propyrisulfuron, cycluron, cyperquat, cyprazine, cyprazole, cypromid, daimu propyZamide, prosulfalin, prosulfocarb, prosulfuron, proxan, ron, dalapon, dazomet, delachlor, desmedipham, desmetryn, prynachlor, pydanon, pyraclonil, pyraflufen-ethyl, pyrasulfo di-allate, dicamba, dichlobenil, dichloralurea, dichlormate, tole, pyrazogyl, pyrazolynate, pyrazosulfuron-ethyl, pyra , dichlorprop-P, dicloSulam, diethamduat, ZOxyfen, , pyributicarb, pyriclor, pyridafol. diethatyl, difenopenten, difenoXuron, difenZoquat, diflufeni pyridate, pyriftalid, pyriminobac, pyrimisulfan, pyrithiobac can, diflufenZopyr, dimefuron, dimepiperate, dimethachlor, Sodium, pyroxasulfone, pyroxSulam, quinclorac, quinmerac, dimethametryn, , dimethenamid-P, dimexano, quinoclamine, quinonamid, rhodethanil, rimsulfuron, dimidazon, dinitramine, dinofenate, dinoprop, dinosam, . S-metolachlor, Sebuthylazine, secbumeton, , dinoterb, diphenamid, dipropetryn, diduat, disul, siduron, , simeton, simetryn, SMA, Sodium arsenite, , diuron, DMPA, DNOC, DSMA, EBEP, eglinazine, Sodium azide, Sodium chlorate, Sulcotrione, Sulfallate, Sulfen endothal, epronaz, EPTC, erbon, esprocarb, ethal fluralin, eth traZone, Sulfometuron, Sulfosate, Sulfosulfuron, Sulfuric acid, benzamide, ethametSulfuron, ethidimuron, ethiolate, Sulglycapin, swep, SYN-523, TCA, tebutam, , ethobenzamid, etobenzamid, ethofumesate, ethoxyfen, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, ethoxysulfuron, etinofen, etnipromid, etobenzanid, EXD, terbuchlor, terbumeton, , terbutryn, tetrafluo fenasulam, , fenoxasulfone, fenteracol, fenthiaprop, ron, thenylchlor, thiazafluoron, thiazopyr, thidiazimin, thidi fentraZamide, fenuron, ferrous Sulfate, flamprop, flamprop aZuron, thiencarbazone-methyl, thifensulfuron, thifensul M, , florasulam, fluazolate, flucarbazone, fluc furn-methyl, thiobencarb, tiocarbazil, tioclorim, etosulfuron, fluchloralin, flufenacet, flufenican, flufenpyr toprameZone, triafamone, tri-allate, triasulfuron, triaziflam, ethyl, flumetSulam, flumezin, flumiclorac-pentyl, tribenuron, tribenuron-methyl, tricamba, triclopyr choline flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoro salt, triclopyr esters and salts, tridiphane, trietazine, triflox glycofen, fluoromidine, fluoronitrofen, fluothiuron, ysulfuron, , triflusulfuron, trifop, trifopsime, trihy US 2014/003 1228A1 Jan. 30, 2014 droxytriazine, trimeturon, tripropindan, tritac tritosulfuron, is utilized to antagonize harmful effects of the compositions Vernolate, Xylachlorand salts, esters, optically active isomers on rice and cereals. In some embodiments, the Safener is and mixtures thereof. cloquintocet (mexyl). 0.125. In some embodiments, the compositions described 0123. The compositions and methods described herein, herein are employed in combination with one or more plant can further be used in conjunction with glyphosate, growth regulators, such as 2.3.5-tri-iodobenzoic acid, IAA, 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase IBA, naphthaleneacetamide, C.-naphthaleneacetic acids, ben inhibitors, glufosinate, glutamine synthetase inhibitors, Zyladenine, 4-hydroxyphenethyl alcohol, kinetin, Zeatin, dicamba, phenoxy auxins, pyridyloxy auxins, synthetic aux endothal, , pentachlorophenol, thidiaZuron, tribu ins, auxin transport inhibitors, aryloxyphenoxypropionates, fos, aviglycine, maleic hydrazide, gibberellins, gibberellic cyclohexanediones, phenylpyrazolines, acetyl CoA carboxy acid, abscisic acid, ancymidol, fosamine, glyphosine, isopy lase (ACCase) inhibitors, imidazolinones, Sulfonylureas, rimol, jasmonic acid, maleic hydrazide, mepiquat, 2.3.5-tri pyrimidinylthiobenzoates, triazolopyrimidines, Sulfonylami iodobenzoic acid, morphactins, dichlorflurenol, flurprimidol, nocarbonyltriazolinones, acetolactate synthase (ALS) or mefluidide, paclobutraZol, tetcyclacis, uniconazole, brassino acetohydroxy acid synthase (AHAS) inhibitors, 4-hydrox lide, brassinolide-ethyl, cycloheximide, ethylene, methasul yphenyl-pyruvate dioxygenase (HPPD) inhibitors, phytoene focarb, prohexadione, triapenthenol and trinexapac. desaturase inhibitors, carotenoid biosynthesis inhibitors, pro I0126. In some embodiments, the plant growth regulators toporphyrinogen oxidase (PPO) inhibitors, cellulose biosyn are employed in one or more crops or settings, such as rice, thesis inhibitors, mitosis inhibitors, microtubule inhibitors, cereal crops, corn, maize, broadleaf crops, oilseed rape/ very long chain fatty acid inhibitors, fatty acid and lipid canola, turf pineapple, Sugarcane, Sunflower, pastures, grass biosynthesis inhibitors, photosystem I inhibitors, photosys lands, rangelands, fallowland, tree and vine orchards, planta tem II inhibitors, triazines, and bromoxynil on glyphosate tion crops, vegetables, and non-crop (ornamentals) settings. tolerant, EPSP synthase inhibitor-tolerant, glufosinate-toler In some embodiments, the plant growth regulator is mixed ant, glutamine synthetase inhibitor-tolerant, dicamba with the compound of formula (I), or mixed with the com tolerant, phenoxy auxin-tolerant, pyridyloxy auxin-tolerant, pound of formula (I) and ACCase inhibitors to cause a pref auxin-tolerant, auxin transport inhibitor-tolerant, arylox erentially advantageous effect on plants. yphenoxypropionate-tolerant, cyclohexanedione-tolerant, I0127. In certain embodiments, the compositions comprise phenylpyrazoline-tolerant, ACCase-tolerant, imidazolinone or the methods utilize (a) the compound of formula I or tolerant, Sulfonylurea-tolerant, pyrimidinylthiobenzoate-tol agriculturally acceptable salt or ester thereof; (b) an ACCase inhibitor; and (c) a third herbicide. In some embodiments, the erant, triazolopyrimidine-tolerant, Sulfonylaminocarbonyl compositions comprise or the methods utilize a compound of triazolinone-tolerant, ALS- or AHAS-tolerant, HPPD Formula I or agriculturally acceptable salt or ester thereof, tolerant, phytoene desaturase inhibitor-tolerant, carotenoid cyhalofop-butyl, and penoXSulam. In some embodiments, the biosynthesis inhibitor tolerant, PPO-tolerant, cellulose bio compound of formula I or agriculturally acceptable salt or synthesis inhibitor-tolerant, mitosis inhibitor-tolerant, micro ester thereof is from about 7 to about 45 weight percent of the tubule inhibitor-tolerant, very long chain fatty acid inhibitor total composition; cyhalofop-butyl is from about 48 to about tolerant, fatty acid and lipid biosynthesis inhibitor-tolerant, 89 weight percent of the total composition, and penoXSulam is photosystem I inhibitor-tolerant, photosystem II inhibitor from about 4 to about 7 weight percent of the total composi tolerant, triazine-tolerant, bromoxynil-tolerant, and crops tion. In certain embodiments, the compound of formula I or possessing multiple or stacked traits conferring tolerance to agriculturally acceptable salt or ester thereof is from about 9 multiple chemistries and/or multiple modes of action via to about 28 weight percent of the total composition; cyhalo single and/or multiple resistance mechanisms. In some fop-butyl is from about 62 to about 88 weight percent of the embodiments, the compound of formula (I) or salt or ester total composition, and penoXSulam is from about 2 to about thereof and complementary herbicide or salt or ester thereof 10 weight percent of the total composition. In some embodi are used in combination with herbicides that are selective for ments, the compound of formula I or agriculturally accept the crop being treated and which complement the spectrum of able salt or ester thereof, or salt or ester thereof, is applied at weeds controlled by these compounds at the application rate a rate from about 2 to about 300 gae/ha (grams acid equiva employed. In some embodiments, the compositions lent/ha); cyhalofop-butyl salt or ester thereof is applied at a described herein and other complementary herbicides are rate from about 25 to about 320 gai/ha (grams active ingre applied at the same time, either as a combination formulation dient/ha), and penoxsulam is applied from about 1 to about 50 or as a tank mix. grai/ha (grams active ingredient/ha). In a further embodi 0.124. In some embodiments, the compositions described ment, the compound of formula I or agriculturally acceptable herein are employed in combination with one or more herbi salt or ester thereof, is applied at a rate from about 1 to about cide safeners, such as AD-67 (MON 4660), benoxacor, 32 gae?ha; cyhalofop-butyl salt or ester thereof is applied at a benthiocarb, brassinolide, cloquintocet (mexyl), cyometrinil, rate from about 25 to about 280 gai/ha, and penoxsulam is daimuron, dichlormid, dicyclonon, dimepiperate, disulfoton, applied from about 2 to about 35 grai/ha. In certain embodi fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furila ments, the methods and compositions utilizing the compound Zole, harpin proteins, isoxadifen-ethyl, jiecaowan, jiecaoxi, of formula (I) or salt or ester thereof in combination with mefenpyr-diethyl, mephenate, naphthalic anhydride (NA), cyhalofop-butyl and penoXSulam, or salt or ester thereof, are oxabetrinil, R291.48 and N-phenyl-sulfonylbenzoic acid used to control ECHCG, CYPRO and FIMMI. amides, to enhance their selectivity. In some embodiments, I0128. In some embodiments, the compositions comprise the safeners are employed in rice, cereal, corn, or maize or the methods utilize a compound of formula I or agricultur settings. In some embodiments, the safener is cloquintocet or ally acceptable salt or ester thereof, cyhalofop-butyl, and an ester or salt thereof. In certain embodiments, cloquintocet bentaZon-sodium. In some embodiments, the compound of US 2014/003 1228A1 Jan. 30, 2014 formula I or agriculturally acceptable salt or ester thereof is to about 28 weight percent of the total composition; cyhalo from about 2 to about 13 weight percent of the total compo fop-butyl is from about 60 to about 63 weight percent of the sition; cyhalofop-butyl is from about 14 to about 20 weight total composition, and bispyribac-Sodium is from about 11 to percent of the total composition, and bentaZon-sodium is about 30 weight percent of the total composition. In some from about 73 to about 78 weight percent of the total compo embodiments, the compound of formula I, or salt or ester sition. In certain embodiments, the compound of formula I or thereof, is applied at a rate from about 2 to about 300 gae?ha; agriculturally acceptable salt or ester thereof is from about 1 cyhalofop-butyl is applied at a rate from about 25 to about 320 to about 9 weight percent of the total composition; cyhalofop gai/ha, and bispyribac-Sodium is applied from about 20 to butyl is from about 15 to about 18 weight percent of the total about 90 grai/ha. In a further embodiment, the compound of composition, and bentazon-sodium is from about 78 to about 84 weight percent of the total composition. In some embodi formula I or agriculturally acceptable salt or ester thereof, is ments, the compound of Formula I, or salt or ester thereof, is applied at a rate from about 1 to about 32 gae?ha; cyhalofop applied at a rate from about 2 to about 300 gae?ha; cyhalofop butyl salt or ester thereof is applied at a rate from about 25 to butyl is applied at a rate from about 25 to about 320 gai/ha, about 280 gai/ha, and bispyribac-Sodium is applied from and bentazon-sodium is applied from about 1 to about 1,500 about 25 to about 75 grai/ha. In certain embodiments, the grai/ha. In a further embodiment, the compound of formula I methods and compositions utilizing the compound of formula or agriculturally acceptable salt or ester thereof, is applied at (I) or salt or ester thereof in combination with cyhalofop a rate from about 1 to about 32 gae?ha; cyhalofop-butyl salt or butyl and bispyribac-sodium, or salt or ester thereof, are used ester thereof is applied at a rate from about 25 to about 280 to control ECHCG and SCPJU. gai/ha, and bentaZon-Sodium is applied from about 210 to I0131. In some embodiments, the compositions comprise about 1,200 grai/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or or the methods utilize the compound of formula I, cyhalofop salt or ester thereof in combination with cyhalofop-butyl and butyl, and imaZamox. In some embodiments, the compound bentaZone sodium, or salt or ester thereof, are used to control of formula I or agriculturally acceptable saltorester thereof is ECHCG and FIMMI. from about 5 to about 44 weight percent of the total compo sition; cyhalofop-butyl is from about 46 to about 77 weight 0129. In some embodiments, the compositions comprise or the methods utilize a compound of the formula I or agri percent of the total composition, and imaZamox is from about culturally acceptable salt or ester thereof, cyhalofop-butyl, 10 to about 18 weight percent of the total composition. In and triclopyr. In some embodiments, the compound of for certain embodiments, the compound of formula I or agricul mula I or agriculturally acceptable saltorester thereofis from turally acceptable saltorester thereof is from about 8 to about about 2 to about 20 weight percent of the total composition; 28 weight percent of the total composition; cyhalofop-butyl is cyhalofop-butyl is from about 20 to about 22 weight percent from about 58 to about 80 weight percent of the total compo of the total composition, and bentaZon-Sodium is from about sition, and imaZamox is from about 12 to about 14 weight 58 to about 78 weight percent of the total composition. In percent of the total composition. In some embodiments, the certain embodiments, the compound of formula I or agricul compound of Formula I, or salt or ester thereof, is applied at turally acceptable saltorester thereof is from about 1 to about a rate from about 2 to about 300 gai/ha; cyhalofop-butyl is 11 weight percent of the total composition; cyhalofop-butyl is applied at a rate from about 25 to about 320 gai/ha, and from about 15 to about 25 weight percent of the total compo imazamox is applied from about 6 to about 70 grai/ha. sition, and triclopyr is from about 64 to about 84 weight 0.132. In some embodiments, the compositions comprise percent of the total composition. In some embodiments, the or the methods utilize a compound of the formula I or agri compound of Formula I, or salt or ester thereof, is applied at culturally acceptable salt or ester thereof, cyhalofop-butyl, a rate from about 2 to about 300 gae/ha; cyhalofop-butyl is and benzobicyclon. In some embodiments, the compound of applied at a rate from about 25 to about 320 gai/ha, and formula I or agriculturally acceptable salt or ester thereof is triclopyr is applied from about 100 to about 840 grae/ha. In a from about 3 to about 33 weight percent of the total compo further embodiment, the compound of formula I or agricul sition; cyhalofop-butyl is from about 32 to about 35 weight turally acceptable saltorester thereof, is applied at a rate from percent of the total composition, and benzobicyclon is from about 1 to about 32 gae/ha; cyhalofop-butyl salt or ester about 33 to about 65 weight percent of the total composition. thereof is applied at a rate from about 25 to about 280 gai/ha, In certain embodiments, the compound of formula I or agri and triclopyr is applied from about 210 to about 560 grae/ha. culturally acceptable salt or ester thereof is from about 3 to In certain embodiments, the methods and compositions uti about 19 weight percent of the total composition; cyhalofop lizing the compound of formula (I) or salt or ester thereof in butyl is from about 32 to about 42 weight percent of the total combination with cyhalofop-butyl and triclopyr, or salt or composition, and benzobicyclon is from about 39 to about 65 ester thereof, are used to control ECHCG and SCPJU. weight percent of the total composition. In some embodi 0130. In some embodiments, the compositions comprise ments, the compound of Formula I, or salt or ester thereof, is or the methods utilize a compound of formula I or agricultur applied at a rate from about 2 to about 300 gai?ha; cyhalofop ally acceptable salt or ester thereof, cyhalofop-butyl, and butyl is applied at a rate from about 25 to about 320 gai/ha, bispyribac-Sodium. In some embodiments, the compound of and benzobicyclon is applied from about 50 to about 300 gr formula I or agriculturally acceptable salt or ester thereof is ai/ha. In a further embodiment, the compound of formula I or from about 4 to about 44 weight percent of the total compo agriculturally acceptable salt or ester thereof, is applied at a sition; cyhalofop-butyl is from about 47 to about 53 weight rate from about 1 to about 32 gae?ha; cyhalofop-butyl salt or percent of the total composition, and bispyribac-Sodium is ester thereof is applied at a rate from about 25 to about 280 from about 9 to about 43 weight percent of the total compo gai/ha, and benzobicyclon is applied from about 50 to about sition. In certain embodiments, the compound of formula I or 300 grai/ha. In certain embodiments, the methods and com agriculturally acceptable salt or ester thereof is from about 6 positions utilizing the compound of formula (I) or Saltorester US 2014/003 1228A1 Jan. 30, 2014 20 thereof in combination with cyhalofop-butyl and bispyribac culturally acceptable salt or ester thereof, fenoxaprop, and sodium, or salt or ester thereof, are used to control ECHCG, penoXSulam. In some embodiments, the compound of for ECHOR and FIMMI. mula I or agriculturally acceptable saltorester thereofis from 0133. In some embodiments, the compositions comprise about 7 to about 61 weight percent of the total composition; or the methods utilize a compound of the formula I or agri fenoxaprop is from about 89 to about 29 weight percent of the culturally acceptable salt or ester thereof, cyhalofop-butyl, total composition, and penoXSulam is from about 4 to about and quinclorac. In some embodiments, the compound of for 10 weight percent of the total composition. In certain embodi mula I or agriculturally acceptable saltorester thereofis from ments, the compound of formula I or agriculturally accept about 2 to about 25 weight percent of the total composition; able salt or ester thereof is from about 9 to about 44 weight cyhalofop-butyl is from about 25 to about 27 weight percent percent of the total composition; fenoxaprop is from about 41 of the total composition, and quinclorac is from about 48 to to about 88 weight percent of the total composition, and about 72 weight percent of the total composition. In certain embodiments, the compound of formula I or agriculturally penoxsulam is from about 3 to about 15 weight percent of the acceptable salt or ester thereof is from about 3 to about 14 total composition. In some embodiments, the compound of weight percent of the total composition; cyhalofop-butyl is Formula I, or salt or ester thereof, is applied at a rate from from about 25 to about 26 weight percent of the total compo about 2 to about 300 gae?ha; fenoxaprop is applied at a rate sition, and quinclorac is from about 54 to about 71 weight from about 25 to about 140 gr ae/ha, and penoXSulam is percent of the total composition. In some embodiments, the applied from about 1 to about 50 grai/ha. compound of formula I, or salt or ester thereof, is applied at a 0.137 In some embodiments, the compositions comprise rate from about 2 to about 300 gae?ha; cyhalofop-butyl is or the methods utilize a compound of the formula I or agri applied at a rate from about 25 to about 320 gai/ha, and culturally acceptable Salt or ester thereof, metamifop, and Quinclorac is applied from about 70 to about 560 grai/ha. penoXSulam. In some embodiments, the compound of for 0134. In some embodiments, the compositions comprise mula I or agriculturally acceptable saltorester thereofis from or the methods utilize a compound of the formula I or agri about 4 to about 46 weight percent of the total composition; culturally acceptable salt or ester thereof, cyhalofop-butyl, metamifop is from about 46 to about 94 weight percent of the and glyphosate. In some embodiments, the compound of total composition, and penoXSulam is from about 2 to about 8 formula I or agriculturally acceptable salt or ester thereof is weight percent of the total composition. In certain embodi from about 1 to about 11 weight percent of the total compo ments, the compound of formula I or agriculturally accept sition; cyhalofop-butyl is from about 11 to about 13 weight able salt or ester thereof is from about 7 to about 30 weight percent of the total composition, and glyphosate is from about percent of the total composition; metamifop is from about 60 78 to about 86 weight percent of the total composition. In to about 90 weight percent of the total composition, and certain embodiments the compound of formula I or agricul penoxsulam is from about 3 to about 10 weight percent of the turally acceptable salt or ester thereof is from about 1.5 to total composition. In some embodiments, the compound of about 5.5 weight percent of the total composition; cyhalofop Formula I, or salt or ester thereof, is applied at a rate from butyl is from about 15 to about 11.5 weight percent of the total about 2 to about 300 gae/ha; metamifop is applied at a rate composition, and glyphosate is from about 83 to about 83.5 from about 10 to about 300 gr ae/ha, and penoxsulam is weight percent of the total composition. In some embodi applied from about 1 to about 50 grai/ha. In a further embodi ments, the compound of Formula I, or salt or ester thereof, is ment, the compound of formula I or agriculturally acceptable applied at a rate from about 2 to about 300 gae?ha; cyhalofop salt or ester thereof, is applied at a rate from about 1 to about butyl is applied at a rate from about 25 to about 320 gai/ha, 32 gae?ha; metamifop salt or ester thereof, is applied at a rate and glyphosate is applied from about 160 to about 2240 gr from about 25 to about 100 gai/ha, and penoxsulam is applied ae/ha. from about 5 to about 35 grai?ha. In certain embodiments, the 0135) In some embodiments, the compositions comprise methods and compositions utilizing the compound of formula or the methods utilize a compound of the formula I or agri (I) or saltorester thereof in combination with metamifop and culturally acceptable salt or ester thereof, cyhalofop-butyl, penoXSulam, or salt or ester thereof, are used to control and glufosinate. In some embodiments, the compound of ECHCG. formula I or agriculturally acceptable salt or ester thereof is 0.138. In some embodiments, the compositions comprise from about 4 to about 14 weight percent of the total compo or the methods utilize a compound of the formula I or agri sition; cyhalofop-butyl is from about 15 to about 45 weight culturally acceptable salt or ester thereof, profoxydim, and percent of the total composition, and glufosinate is from penoXSulam. In some embodiments, the compound of for about 51 to about 71 weight percent of the total composition. mula I or agriculturally acceptable saltorester thereofis from In certain embodiments, the compound of formula I or agri about 13 to about 55 weight percent of the total composition; culturally acceptable salt or ester thereof is from about 4 to profoxydim is from about 36 to about 80 weight percent of the about 7 weight percent of the total composition; cyhalofop total composition, and penoXSulam idiments, the compound butyl is from about 16 to about 38 weight percent of the total of formula I or agriculturally acceptable saltorester thereof is composition, and glufosinate is from about 58 to about 77 from about 19 to about 39 weight percent of the total compo weight percent of the total composition. In some embodi sition; profoxydim is from about 50 to about 74 weight per ments, the compound of Formula I, or salt or ester thereof, is cent of the total composition, and penoXSulam is from about applied at a rate from about 2 to about 300 gae?ha; cyhalofop 3 to about 10 weight percent of the total composition. In some butyl is applied at a rate from about 25 to about 320 gai/ha, embodiments, the compound of Formula I, or salt or ester and glufosinate is applied from about 28 to about 1560 gr thereof, is applied at a rate from about 2 to about 300 gae?ha; ai/ha. profoxydim is applied at a rate from about 12 to about 200 gr 0136. In some embodiments, the compositions comprise ai/ha, and penoXSulam is applied from about 1 to about 50 gr or the methods utilize a compound of the formula I or agri ai/ha. US 2014/003 1228A1 Jan. 30, 2014

0.139. In some embodiments, the compositions comprise sition; cyhalofop-butyl is from about 9 to about 28 weight or the methods utilize a compound of the formula I or agri percent of the total composition, and ipfencarbazone is from culturally acceptable salt or ester thereof, cyhalofop-butyl, about 45 to about 90 weight percent of the total composition. and benfuresate. In some embodiments, the compound of In certain embodiments, the compound of formula I or agri formula I or agriculturally acceptable salt or ester thereof is culturally acceptable salt or ester thereof is from about 1 to from about 2 to about 32 weight percent of the total compo about 15 weight percent of the total composition; cyhalofop sition; cyhalofop-butyl is from about 34 to about 35 weight butyl is from about 14 to about 33 weight percent of the total percent of the total composition, and benfuresate is from composition, and ipfencarbazone is from about 52 to about 85 about 33 to about 64 weight percent of the total composition. weight percent of the total composition. In some embodi In certain embodiments, the compound of formula I or agri ments, the compound of Formula I, or salt or ester thereof, is culturally acceptable salt or ester thereof is from about 3 to applied at a rate from about 2 to about 300 gae?ha; cyhalofop about 19 weight percent of the total composition; cyhalofop butyl is applied at a rate from about 25 to about 320 gai/ha, butyl is from about 32 to about 42 weight percent of the total and ipfencarbazone is applied from about 250 to about 500 gr composition, and benfuresate is from about 39 to about 64 ai/ha. weight percent of the total composition. In some embodi 0143. In some embodiments, the compositions comprise ments, the compound of Formula I, or salt or ester thereof, is or the methods utilize a compound of the formula I or agri applied at a rate from about 2 to about 300 gae?ha; cyhalofop culturally acceptable salt or ester thereof, cyhalofop-butyl, butyl, is applied at a rate from about 25 to about 320 gai/ha, and mefenacet. In some embodiments, the compound of for and benfuresate is applied from about 50 to 300 grai/ha. mula I or agriculturally acceptable saltorester thereofis from 0140. In some embodiments, the compositions comprise about 1 to about 14 weight percent of the total composition; or the methods utilize a compound of the formula I or agri cyhalofop-butyl is from about 9 to about 14 weight percent of culturally acceptable salt or ester there of cyhalofop-butyl, the total composition, and mefenacet is from about 72 to and fentraZamide. In some embodiments, the compound of about 90 weight percent of the total composition. In certain formula I or agriculturally acceptable salt or ester thereof is embodiments. Formula I is from about 2 to about 7 weight from about 5 to about 33 weight percent of the total compo percent of the total composition; cyhalofop-butyl is from sition; cyhalofop-butyl is from about 35 to about 58 weight about 14 to about 16 weight percent of the total composition, percent of the total composition, and fentraZamide is from and mefenacet is from about 77 to about 85 weight percent of about 32 to about 37 weight percent of the total composition. the total composition. In some embodiments, the compound In certain embodiments, the compound of formula I or agri of Formula I, or salt or ester thereof, is applied at a rate from culturally acceptable salt or ester thereof is from about 6 to about 2 to about 300 gae?ha; cyhalofop-butyl is applied at a about 19 weight percent of the total composition; cyhalofop rate from about 25 to about 320 gai/ha, and mefenacet is butyl is from about 39 to about 63 weight percent of the total applied from about 250 to about 1600 grai/ha. In a further composition, and fentraZamide is from about 31 to about 40 embodiment, the compound of formula I or agriculturally weight percent of the total composition. In some embodi acceptable salt or ester thereof, is applied at a rate from about ments, the compound of Formula I, or salt or ester thereof, is 1 to about 32 gae?ha; cyhalofop-butyl salt or ester thereof is applied at a rate from about 2 to about 300 gae?ha; cyhalofop applied at a rate from about 25 to about 280 gai/ha, and butyl is applied at a rate from about 25 to about 320 gai/ha, mefenacet is applied from about 75 to about 560 grai/ha. and fentraZamide is applied from about 16 to about 300 gr 0144. In some embodiments, the compositions comprise ai/ha. or the methods utilize a compound of the formula I or agri 0141. In some embodiments, the compositions comprise culturally acceptable salt or ester thereof, cyhalofop-butyl, or the methods utilize a compound of the formula I or agri and oxazichlomafone. In some embodiments, the compound culturally acceptable salt or ester thereof, cyhalofop-butyl, of formula I or agriculturally acceptable saltorester thereof is and indanofan. In some embodiments, the compound of for from about 6 to about 43 weight percent of the total compo mula I or agriculturally acceptable saltorester thereofis from sition; cyhalofop-butyl is from about 42 to about 76 weight about 4 to about 33 weight percent of the total composition; percent of the total composition, and oxazichlomafone is cyhalofop-butyl is from about 35 to about 48 weight percent from about 11 to about 18 weight percent of the total compo of the total composition, and indanofan is from about 32 to sition. In certain embodiments, the compound of formula I or about 48 weight percent of the total composition. In certain agriculturally acceptable salt or ester thereof is from about 7 embodiments, the compound of formula I or agriculturally to about 27 weight percent of the total composition; cyhalo acceptable salt or ester thereof si from about 5 to about 19 fop-butyl is from about 58 to about 77 weight percent of the weight percent of the total composition; cyhalofop-butyl is total composition, and oxazichlomafone is from about 14 to from about 42 to about 48 weight percent of the total compo about 15 weight percent of the total composition. In some sition, and indanofan is from about 39 to about 48 weight embodiments, the compound of Formula I, or salt or ester percent of the total composition. In some embodiments, the thereof, is applied at a rate from about 2 to about 300 gae?ha; compound of Formula I, or salt or ester thereof, is applied at cyhalofop-butyl is applied at a rate from about 25 to about 320 a rate from about 2 to about 300 gae/ha; cyhalofop-butyl is gai/ha, and oxazichlomafone is applied from about 6 to about applied at a rate from about 25 to about 320 gai/ha, and 80 grai/ha. In some embodiments, the compositions com indanofan is applied from about 25 to about 300 grai/ha. prise or the methods utilize a compound of the formula I or 0142. In some embodiments, the compositions comprise agriculturally acceptable salt or ester thereof, cyhalofop-bu or the methods utilize a compound of the formula I or agri tyl, or pretilachlor. culturally acceptable salt or ester thereof, cyhalofop-butyl, 0145. In some embodiments, the compound of formula I and ipfencarbazone. In some embodiments, the compound of or agriculturally acceptable salt or ester thereof is from about formula I or agriculturally acceptable salt or ester thereof is 3 to about 22 weight percent of the total composition; cyha from about 1 to about 27 weight percent of the total compo lofop-butyl iss from about 23 to about 38 weight percent of US 2014/003 1228A1 Jan. 30, 2014 22 the total composition, and pretilachlor is from about 55 to a rate from about 2 to about 300 gae/ha; cyhalofop-butyl is about 58 weight percent of the total composition. In certain applied at a rate from about 25 to about 320 gai/ha, and embodiments, the compound of formula I or agriculturally pyriftalid is applied from about 45 to about 90 grai?ha. acceptable salt or ester thereof is from about 3 to about 13 0149. In some embodiments, the compound of formula I weight percent of the total composition; cyhalofop-butyl is or agriculturally acceptable salt or ester thereof, cyhalofop from about 26 to about 32 weight percent of the total compo butyl, and pyrimisulfan. In some embodiments, the com sition, and pretilachlor is from about 61 to about 65 weight pound of formula I or agriculturally acceptable Salt or ester percent of the total composition. In some embodiments, the thereof is from about 7 to about 46 weight percent of the total compound of Formula I, or salt or ester thereof, is applied at composition; cyhalofop-butyl is from about 48 to about 85 a rate from about 2 to about 300 gae/ha; cyhalofop-butyl is weight percent of the total composition, and pyrimisulfan is applied at a rate from about 25 to about 320 gai/ha, and from about 6 to about 8 weight percent of the total composi pretilachlor is applied from about 38 to about 750 grai/ha. tion. In certain embodiments, Formula I is from about 9 to 0146 In some embodiments, the compound of formula I about 29 weight percent of the total composition; cyhalofop or agriculturally acceptable salt or ester thereof, cyhalofop butyl is from about 63 to about 84 weight percent of the total butyl, and propyrisulfuron. In some embodiments, the com composition, and pyrimisulfan is from about 7 to about 8 pound of formula I or agriculturally acceptable Salt or ester weight percent of the total composition. In some embodi thereof is from about 5 to about 42 weight percent of the total ments, the compound of Formula I, or salt or ester thereof, is composition; cyhalofop-butyl is from about 44 to about 66 applied at a rate from about 2 to about 300 gae?ha; cyhalofop weight percent of the total composition, and propyrisulfuron butyl is applied at a rate from about 25 to about 320 gai/ha, is from about 14 to about 29 weight percent of the total and pyrimisulfan is applied from about 2.5 to about 40 gr composition. In certain embodiments, the compound of for ai/ha. mula I or agriculturally acceptable saltorester thereofis from 0150. In some embodiments, the compositions described about 7 to about 26 weight percent of the total composition; herein are employed in combination with one or more herbi cyhalofop-butyl is from about 56 to about 66 weight percent cide safeners, such as AD-67 (MON 4660), benoxacor, of the total composition, and propyrisulfuron is from about 18 benthiocarb, brassinolide, cloquintocet (mexyl), cyometrinil, to about 27 weight percent of the total composition. In some daimuron, dichlormid, dicyclonon, dimepiperate, disulfoton, embodiments, the compound of Formula I, or salt or ester fenchlorazole-ethyl, fenclorim, furilazole, fluxofenim, furila thereof, is applied at a rate from about 2 to about 300 gae?ha; Zole, harpin proteins, isoxadifen-ethyl, jiecaowan, jiecaoxi, cyhalofop-butyl is applied at a rate from about 25 to about 320 mefenpyr-diethyl, mephenate, naphthalic anhydride (NA), gai/ha, and propyrisulfuron is applied from about 11 to about oxabetrinil, R291.48 and N-phenyl-sulfonylbenzoic acid 100 grai/ha. amides, to enhance their selectivity. In some embodiments, 0147 In some embodiments, the compound of formula I the Safener is cloquintocet or an ester or salt thereof. In certain or agriculturally acceptable salt or ester thereof, cyhalofop embodiments, cloquintocet is utilized to antagonize harmful butyl, and pyraclonil. In some embodiments, the compound effects of the compositions on rice and cereals. In some of formula I or agriculturally acceptable saltorester thereof is embodiments, the safener is cloquintocet (mexyl). from about 1 to about 33 weight percent of the total compo 0151. In some embodiments, compositions provided sition; cyhalofop-butyl is from about 12 to about 33 weight herein further comprise at least one agriculturally acceptable percent of the total composition, and pyraclonil is from about adjuvant or carrier. Suitable adjuvants or carriers should not 33 to about 87 weight percent of the total composition. In be phytotoxic to valuable crops, particularly at the concen certain embodiments, the compound of formula I or agricul trations employed in applying the compositions for selective turally acceptable saltorester thereof is from about 2 to about weed control in the presence of crops, and should not react 19 weight percent of the total composition; cyhalofop-butyl is chemically with herbicidal components or other composition from about 20 to about 42 weight percent of the total compo ingredients. Such mixtures can be designed for application sition, and pyraclonil is from about 39 to about 78 weight directly to weeds or their locus or can be concentrates or percent of the total composition. In some embodiments, the formulations that are normally diluted with additional carri compound of Formula I, or salt or ester thereof, is applied at ers and adjuvants before application. They can be solids, Such a rate from about 2 to about 300 gae/ha; cyhalofop-butyl is as, for example, dusts, granules, water-dispersible granules, applied at a rate from about 25 to about 320 gai/ha, and or wettable powders, or liquids, such as, for example, emul pyraclonil is applied from about 180 to about 300 grai/ha. sifiable concentrates, Solutions, emulsions or Suspensions. 0148. In some embodiments, the compound of formula I They can also be provided as a pre-mix or tank mixed. or agriculturally acceptable salt or ester thereof, cyhalofop 0152 Suitable agricultural adjuvants and carriers include, butyl, and pyriftalid. In some embodiments, the compound of but are not limited to, crop oil concentrate; nonylphenol formula I or agriculturally acceptable salt or ester thereof is ethoxylate; benzylcocoalkyldimethyl quaternary ammonium from about 3 to about 42 weight percent of the total compo salt, blend of petroleum hydrocarbon, alkyl esters, organic sition; cyhalofop-butyl is from about 35 to about 45 weight acid, and anionic surfactant; C-C alkylpolyglycoside: percent of the total composition, and pyriftalid is from about phosphated alcohol ethoxylate; natural primary alcohol (C- 13 to about 62 weight percent of the total composition. In C) ethoxylate; di-sec-butylphenol EO-PO block copoly certain embodiments, the compound of formula I or agricul mer, polysiloxane-methyl cap: nonylphenol ethoxylate- turally acceptable saltorester thereof is from about 5 to about ammonium nitrate; emulsified methylated seed oil; tridecyl 27 weight percent of the total composition; cyhalofop-butyl is alcohol (synthetic) ethoxylate (8EO); tallow amine ethoxy from about 47 to about 57 weight percent of the total compo late (15 EO); PEG(400) dioleate-99. sition, and pyriftalid is from about 16 to about 48 weight 0153. Liquid carriers that can be employed include water percent of the total composition. In some embodiments, the and organic solvents. The organic solvents include, but are compound of Formula I, or salt or ester thereof, is applied at not limited to, petroleum fractions or hydrocarbons such as US 2014/003 1228A1 Jan. 30, 2014

mineral oil, aromatic solvents, paraffinic oils, and the like; 0157. Other exemplary additives for use in the composi Vegetable oils such as Soybean oil, rapeseed oil, olive oil, tions provided herein include but are not limited to compati castor oil, Sunflower seed oil, coconut oil, corn oil, cottonseed bilizing agents, antifoam agents, sequestering agents, neu oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tralizing agents and buffers, corrosion inhibitors, dyes, tung oil and the like; esters of the above vegetable oils; esters odorants, spreading agents, penetration aids, Sticking agents, of monoalcohols or dihydric, trihydric, or other lower poly dispersing agents, thickening agents, freezing point depres alcohols (4-6 hydroxy containing). Such as 2-ethyl hexyl sants, antimicrobial agents, and the like. The compositions Stearate, n-butyl oleate, isopropyl myristate, propylene glycol may also contain other compatible components, for example, dioleate, di-octyl Succinate, di-butyl adipate, di-octyl phtha other herbicides, plant growth regulants, fungicides, insecti late and the like; esters of mono, di and polycarboxylic acids cides, and the like and can be formulated with liquid fertiliz and the like. Specific organic solvents include, but are not ers or Solid, particulate fertilizer carriers such as ammonium limited to toluene, Xylene, petroleum naphtha, crop oil, nitrate, urea and the like. acetone, methyl ethyl ketone, cyclohexanone, trichloroethyl 0158. In some embodiments, the concentration of the ene, perchloroethylene, ethyl acetate, amyl acetate, butyl active ingredients in the compositions described herein is acetate, propylene glycol monomethyl and diethylene from about 0.0005 to 98 percent by weight. In some embodi glycol monomethyl ether, methyl alcohol, ethyl alcohol, iso ments, the concentration is from about 0.0006 to 90 percent propyl alcohol, amyl alcohol, ethylene glycol, propylene gly by weight. In compositions designed to be employed as con col, glycerine, N-methyl-2-pyrrolidinone, N,N-dimethyl centrates, the active ingredients, in certain embodiments, are alkylamides, dimethyl sulfoxide, liquid fertilizers and the present in a concentration from about 0.1 to 98 weight per like. In certain embodiments, Water is the carrier for the cent, and in certain embodiment’s about 0.5 to 90 weight dilution of concentrates. percent. Such compositions are, in certain embodiments, diluted with an inert carrier, such as water, before application. 0154 Suitable solid carriers include but are not limited to The diluted compositions usually applied to weeds or the talc, pyrophyllite clay, silica, attapulgus clay, kaolin clay, locus of weeds contain, in certain embodiments, about 0.0006 kieselguhr, chalk, diatomaceous earth, lime, calcium carbon to 10.0 weight percent active ingredient and in certain ate, bentonite clay, Fuller's earth, cottonseed hulls, wheat embodiments contain about 0.01 to 5.0 weight percent. flour, soybean flour, pumice, wood flour, walnut shell flour, 0159. The present compositions can be applied to weeds lignin, cellulose, and the like. or their locus by the use of conventional ground or aerial 0155. In some embodiments, the compositions described dusters, sprayers, and granule applicators, by addition to irri herein further comprise one or more surface-active agents. In gation or paddy water, and by other conventional means Some embodiments, such surface-active agents are employed known to those skilled in the art. in both solid and liquid compositions, and in certain embodi 0160 The described embodiments and following ments those designed to be diluted with carrier before appli examples are for illustrative purposes and are not intended to cation. The Surface-active agents can be anionic, cationic or limit the scope of the claims. Other modifications, uses, or nonionic in character and can be employed as emulsifying combinations with respect to the compositions described agents, wetting agents, Suspending agents, or for other pur herein will be apparent to a person of ordinary skill in the art poses. Surfactants which may also be used in the present without departing from the spirit and scope of the claimed formulations are described, inter alia, in “McCutcheon's Subject matter. Detergents and Emulsifiers Annual MC Publishing Corp., Ridgewood, N.J., 1998 and in “Encyclopedia of Surfactants.” EXAMPLES Vol. I-III, Chemical Publishing Co., New York, 1980-81. Surface-active agents include, but are not limited to salts of (0161 Results in Examples I, II, III, IV VI, and VII are alkyl sulfates, such as diethanolammonium lauryl Sulfate; greenhouse trial results. alkylarylsulfonate salts, such as calcium dodecylbenzene Sulfonate; alkylphenol-alkylene oxide addition products, Example I Such as nonylphenol-Cs ethoxylate; alcohol-alkylene oxide addition products, such as tridecyl alcohol-C ethoxylate: Evaluation of Postemergence Foliar-Applied Soaps, such as Sodium Stearate; alkyl-naphthalene-Sulfonate Herbicidal Mixtures for Weed Control in Direct salts, such as Sodium dibutylnaphthalenesulfonate; dialkyl Seeded Rice esters of sulfo Succinate salts, such as sodium di(2-ethylhexyl) 0162 Seeds or nutlets of the desired test plant species SulfoSuccinate; Sorbitol esters, such as Sorbitol oleate; qua were planted in a Soil matrix prepared by mixing a loam or ternary amines, such as lauryl trimethylammonium chloride; sandy loam soil (e.g., 28.6 percent silt, 18.8 percent clay, and polyethylene glycol esters offatty acids, such as polyethylene 52.6 percent sand, with a pH of about 5.8 and an organic glycol Stearate; block copolymers of ethylene oxide and pro matter content of about 1.8 percent) and calcareous grit in an pylene oxide; salts of mono and dialkyl phosphate esters; 80 to 20 ratio. The soil matrix was contained in plastic pots Vegetable or seed oils such as Soybean oil, rapeseed/canola with a Volume of 1 quart and a Surface area of 83.6 square oil, olive oil, castor oil, Sunflower seed oil, coconut oil, corn centimeters (cm). When required to ensure good germina oil, cottonseed oil, linseed oil, palm oil, peanut oil, safflower tion and healthy plants, a fungicide treatment and/or other oil, Sesame oil, tung oil and the like; and esters of the above chemical or physical treatment was applied. The plants were Vegetable oils, and in certain embodiments, methyl esters. grown for 8-22 days in a greenhouse with an approximate 14 0156. In some embodiments, these materials, such as Veg hr photoperiod which was maintained at about 29° C. during etable or seed oils and their esters, can be used interchange the day and 26°C. during the night. Nutrients (Peters Excel(R) ably as an agricultural adjuvant, as a liquid carrier or as a 15-5-15 5-Ca 2-Mg and iron chelate) were applied in the Surface active agent. irrigation Solution as needed and water was added on a regular US 2014/003 1228A1 Jan. 30, 2014 24 basis. Supplemental lighting was provided with overhead Solutions. If a test compound did not dissolve readily, the metal halide 1000-Watt lamps as necessary. The plants were mixture was warmed and/or Sonicated. Application solutions employed for testing when they reached the first through were prepared by adding an appropriate amount of each stock fourth true leaf stage. Solution (e.g., 1 mL) and diluted to the appropriate final 0163 Treatments consisted of the acid or esters of concentrations with the addition of 10 mL of an aqueous 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-meth mixture of 1.25% (v/v) crop oil concentrate so that the final oxy-phenyl)pyridine-2-carboxylic acid (Compound A), each spray solutions contained 1.25+/-0.05% (v/v) crop oil con formulated as an SC (Suspension concentrate), and various Centrate. herbicidal components alone and in combination. Forms of compound A were applied on an acid equivalent basis. 0.167 For treatments comprised of technical compounds, Forms of compound A (compound of formula I) tested weighed amounts can be placed individually in 25 mL glass include: vials and dissolved in a volume of 97:3 V/vacetone/DMSO to obtain 12x Stock solutions. If a test compound does not dis Solve readily, the mixture can be warmed and/or Sonicated.

Compound A Application Solutions can be prepared by adding an appro priate amount of each stock solution (e.g., 1 mL) and diluted to the appropriate final concentrations with the addition of 10 mL of an aqueous mixture of 1.5% (v/v) crop oil concentrate so that the final spray solutions contain 1.25% (v/v) crop oil concentrate. When technical materials are used, the concen trated Stock Solutions can be added to the spray Solutions so that the final acetone and DMSO concentrations of the appli cation solutions are 16.2% and 0.5%, respectively. 0168 For treatments comprised of formulated and techni cal compounds, weighed amounts of the technical materials can be placed individually in 25 mL glass vials and dissolved Compound A in a volume of 97:3 V/v acetone/DMSO to obtain 12x stock Solutions, and measured amounts of the formulated com pounds can be placed individually in 25 mL glass vials and diluted in a volume of 1.5% (v/v) crop oil concentrate or water to obtain 12x Stock solutions. If a test compound does not dissolve readily, the mixture can be warmed and/or Sonicated. Application Solutions can be prepared by adding an appro priate amount of each stock solution (e.g., 1 mL) and diluted to the appropriate final concentrations with the addition of an appropriate amount of an aqueous mixture of 1.5% (v/v) crop oil concentrate so that the final spray solutions contain 1.25% (v/v) crop oil concentrate. As required, additional water and/ Benzyl Ester or 97:3 V/vacetone/DMSO can be added to individual appli cation solutions so that the final acetone and DMSO concen 0164. Other herbicidal components were applied on an trations of the application solutions being compared are 8.1% acid equivalent (ae) or active ingredient (ai) basis and and 0.25%, respectively. included acetyl coA carboxylase (ACCase)-inhibiting herbi 0169 All stock solutions and applications solutions were cides (cyclohexanedione and aryloxyphenoxypropionate visually inspected for compound compatibility prior to appli chemical classes) cyhalofop-butyl formulated as Clincher(R) cation. Spray Solutions were applied to the plant material with SF (285 grai/LEC), diclofop-methyl formulated as Hoelon(R) an overhead Mandel track sprayer equipped with a 8002E 3EC, fenoxaprop-p-ethyl--isoxadifen-ethyl formulated as nozzles calibrated to deliver 187L/ha over an application area RiceStar R. HT (0.58 lb/gal EC), fenoxaprop-p-ethyl-mefen of 0.503 m at a spray height of 18 to 20 inches (46 to 50 cm) pyr diethyl formulated as Puma(R) 1EC, metamifop formu above average plant canopy height. Control plants were lated as Metamifop EC, haloxyfop-methyl formulated as Gal sprayed in the same manner with the solvent blank. lant Super(R), fluazifop-p-butyl formulated as Fusilade(RDX, quizalofop-p-ethyl formulated as Assure R II, profoxydim 0170 The treated plants and control plants were placed in formulated as Aura.R. 20EC, clethodim applied as Intensity(R), a greenhouse as described above and watered by Sub-irriga sethoxydim formulated as Poast(R), and tralkoxydim formu tion to prevent wash-off of the test compounds. After approxi lated as Achieve R. mately 3 weeks, the condition of the test plants as compared 0.165 Treatment requirements were calculated based upon with that of the untreated plants was determined visually and the rates being tested, the concentration of active ingredientor scored on a scale of 0 to 100 percent where 0 corresponds to acid equivalent in the formulation, and a 12 mL application no injury or growth inhibition and 100 corresponds to com Volume at a rate of 187 L/ha. plete kill. 0166 For treatments comprised of formulated com 0171 Colby's equation was used to determine the herbi pounds, measured amounts of compounds were placed indi cidal effects expected from the mixtures (Colby, S. R. 1967. vidually in 25 mL glass vials and diluted in a volume of 1.25% Calculation of the synergistic and antagonistic response of (v/v) Agri-Dex(R) crop oil concentrated to obtain 12x stock herbicide combinations. Weeds 15:20-22.). US 2014/003 1228A1 Jan. 30, 2014 25

0172. The following equation was used to calculate the TABLE 3 expected activity of mixtures containing two active ingredi Synergistic Activity of Foliar-Applied Compound A Acid ents, A and B: and Fenoxaprop-p-ethyl + Isoxadifen-ethyl Herbicidal Expected=A+B-(AxB/100) Compositions on Weed Control in a Rice Cropping System. Fenoxaprop Visual Weed 0173 A observed efficacy of active ingredient A at the p-ethyl + Control (%)- same concentration as used in the mixture. Compound Isoxadifen 2ODAA AAcid ethyl CYPDI 0.174 B-observed efficacy of active ingredient B at the same concentration as used in the mixture. gae/ha. Obs Exp 0.175. The compounds tested, application rates employed, 4.38 O 8O O 17.5 O plant species tested, and results are given in Tables 1-21. O 35 O O 70 O TABLE 1. 4.38 17.5 70 8O 4.38 35 99 8O 4.38 70 95 8O Synergistic Activity of Foliar-Applied Compound AAcid and Cyhalofop-Butyl Herbicidal Compositions Fenoxaprop Visual Weed p-ethyl + Control (%)- on Weed Control in a Rice Cropping System. Compound Isoxadifen 2ODAA AAcid ethyl CYPES Visual Weed Control (%)- gae/ha. Obs Exp Compound Cyhalofop- 26 DAA 4.38 O 30 AAcid butyl ISCRU 8.75 O 70 O 17.5 O gae?ha gai?ha Obs Exp O 35 O O 70 O 4.38 17.5 30 30 8.75 O 37 8.75 17.5 1OO 70 4.38 35 40 30 17.5 O 63 8.75 35 90 70 O 140 10 4.38 70 8O 30 8.75 140 63 43 8.75 70 99 70 17.5 140 82 67 Fenoxaprop Visual Weed p-ethyl + Control (%)- Visual Weed Compound Isoxadifen 2ODAA AAcid ethyl SCPU Control (%)- Compound Cyhalofop- 2ODAA gae/ha. Obs Exp AAcid butyl IPOHE 4.38 O 60 O 17.5 50 gae?ha gai?ha Obs Exp O 35 30 O 70 30 19.4 O 15 4.38 17.5 1OO 8O 4.38 35 95 72 O 28O O 4.38 70 95 72 19.4 28O 55 15 gaitha refers to concentration offenoxaprop-p-ethyl

TABLE 2 TABLE 4 Synergistic Activity of Foliar-Applied Compound A Synergistic Activity of Foliar-Applied Compound A Benzyl Benzyl Ester and Cyhalofop-Butyl Herbicidal Compositions Ester and Fenoxaprop-p-ethyl + Isoxadifen-ethyl Herbicidal On Weed Control in a Rice Cropping System. Compositions on Weed Control in a Rice Cropping System. Visual Weed Fenoxaprop- Visual Weed Compound Control (%)- Compound p-ethyl + Control (%)- A Benzyl Cyhalofop- 26 DAA A Benzyl Isoxadifen- 2ODAA Ester butyl ISCRU Ester ethyl CYPES gae?ha gai?ha Obs Exp gae/ha. gai?ha Obs Exp 8.75 O 18 4.38 O 70 17.5 O 33 8.75 O 8O O 140 10 17.5 O 95 8.75 140 53 27 O 17.5 O 17.5 140 40 40 O 35 O O 70 O 4.38 17.5 8O 70 US 2014/003 1228A1 Jan. 30, 2014 26

TABLE 4-continued TABLE 6-continued Synergistic Activity of Foliar-Applied Compound A Benzyl Synergistic Activity of Foliar-Applied Compound A Acid Ester and Fenoxaprop-p-ethyl -- Isoxadi?en-ethyl Herbicidal and Haloxyfop-methyl Herbicidal Compositions on Control Compositions on Weed Control in a Rice Cropping System. of Weeds Common to Rice Cropping Systems. 8.75 17.5 95 8O 17.5 17.5 95 95 4.38 13.5 60 40 30 10 4.38 35 8O 70 8.75 13.5 85 60 35 30 8.75 35 90 8O 17.5 13.5 95 85 55 40 17.5 35 99 95 4.38 27 40 40 2O 10 4.38 70 8O 70 8.75 27 75 60 40 30 8.75 70 95 8O 17.5 27 99 85 60 40 17.5 70 100 95 Fenoxaprop- Visual Weed Visual Weed Compound p-ethyl + Control (%)- Control (%)- A Benzyl Isoxadifen- 2ODAA Compound Haloxyfop- 2ODAA Ester ethyl CYPIR AAcid methyl SCPU gae?ha gai?ha Obs Exp gae/ha. gai?ha Obs Exp

4.38 O 15 4.38 O 70 O 17.5 O 8.75 O 95 O 35 O O 6.75 O O 70 O O 13.5 O 4.38 17.5 70 15 4.38 35 60 15 O 27 O 4.38 70 70 15 4.38 6.75 1OO 70 8.75 6.75 1OO 95 gaitha refers to concentration offenoxaprop-p-ethyl 4.38 13.5 1OO 70 8.75 13.5 1OO 95 4.38 27 1OO 70 TABLE 5 8.75 27 1OO 95 Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Fenoxaprop-p-ethyl + Mefenpyr-diethyl Herbicidal Compositions On Control of Weeds Common to Rice Cropping Systems. TABLE 7 Fenoxaprop- Visual Weed Synergistic Activity of Foliar-Applied Compound A Benzyl Compound p-ethyl + Control (%)- Ester and Haloxyfop-methyl Herbicidal Compositions on A Benzyl Mefenpyr- 2ODAA Control of Weeds Common to Rice Cropping Systems. Ester diethyl CYPIR Visual Weed gae?ha gai?ha Obs Exp Compound Control (%)- A Benzyl Haloxyfop- 2ODAA 8.75 O 35 Ester methyl BRAPP O 11.5 O O 4623 O gae/ha. gai?ha Obs Exp 8.75 11.5 8O 35 4.38 O 50 8.75 23 85 35 8.75 O 70 8.75 46 50 35 O 6.75 O O 13.5 O gaitha refers to concentration offenoxaprop-p-ethyl 4.38 6.75 60 50 8.75 6.75 70 70 4.38 13.5 70 50 TABLE 6 8.75 13.5 85 70 Synergistic Activity of Foliar-Applied Compound A Acid Visual Weed and Haloxyfop-methyl Herbicidal Compositions on Control Compound Control (%)- of Weeds Common to Rice Cropping Systems. A Benzyl Haloxyfop- 2ODAA Ester methyl SCPU Compound Haloxyfop- Visual Weed Control (%) - 20 DAA gae/ha. gai?ha Obs Exp AAcid methyl ECHCO IPOHE 4.38 O 30 gae/ha. gai?ha Obs Exp Obs Exp 8.75 O 60 O 6.75 O 4.38 O 40 10 O 13.5 O 8.75 O 60 30 O 27 O 17.5 O 85 40 4.38 6.75 1OO 30 O 6.75 O O 8.75 6.75 1OO 60 O 13.5 O O 4.38 13.5 99 30 O 27 O O 8.75 13.5 1OO 60 4.38 6.75 60 40 10 10 4.38 27 90 30 8.75 6.75 65 60 30 30 8.75 27 1OO 60 17.5 6.75 70 85 60 40 US 2014/003 1228A1 Jan. 30, 2014 27

TABLE 8 TABLE 10 Synergistic Activity of Foliar-Applied Compound A Acid Synergistic Activity of Foliar-Applied Compound and Fluazifop-p-butyl Herbicidal Compositions on Control AAcid and Metamifop Herbicidal Compositions of Weeds Common to Rice Cropping Systems. on Weed Control in a Rice Cropping System. Visual Weed Control (%)- Compound Fluazifop 19 DAA Visual Weed AAcid p-butyl IPOHE Control (%)- gae/ha. gae/ha. Obs Exp Compound 24 DAA 4.38 O O AAcid Metamifop IPOHE 8.75 O 10 17.5 O 35 O 45 O gae?ha gai?ha Obs Exp O 90 O O 18O O 4.38 O 10 4.38 45 10 O 8.75 45 10 10 8.75 O 10 17.5 45 50 35 17.5 O 30 4.38 90 10 O 8.75 90 25 10 O 150 17.5 90 15 35 4.38 150 15 10 4.38 18O 10 O 8.75 18O 35 10 8.75 150 25 10 17.5 18O 40 35 17.5 150 40 30

TABLE 11 TABLE 9 Synergistic Activity of Foliar-Applied Compound A Benzyl Synergistic Activity of Foliar-Applied Compound Ester and Fluazifop-p-butyl Herbicidal Compositions on A Benzyl Ester and Metamifop Herbicidal Compositions Control of Weeds Common to Rice Cropping Systems. on Weed Control in a Rice Cropping System. Visual Weed Visual Weed Compound Control (%)- Compound Control (%)- A Benzyl Fluazifop 19 DAA A Benzyl 22 DAA Ester p-butyl IPOHE Ester Metamifop ECHCG gae/ha. gae/ha. gae?ha gai?ha Obs Exp 4.38 O 8 O 35 8.75 O 16 O 65 O 45 O 90 32 O 8O O 18O O 9.38 O 4.38 45 O 18.75 40 8.75 45 O 37.5 70 4.38 90 8 9.38 60 35 8.75 90 16 9.38 8O 65 4.38 18O 32 9.38 90 8O 8.75 18O 8 18.75 85 61 16 18.75 95 79 32 18.75 99 88 8 37.5 100 81 TABLE 12 16 37.5 100 90 32 37.5 99 94 Synergistic Activity of Foliar-Applied Compound A Acid and Quizalofop-p-ethyl Herbicidal Compositions on Control Visual Weed of Weeds Common to Rice Cropping Systems. Compound Control (%)- A Benzyl 22 DAA Visual Weed Ester Metamifop IPOHE Control (%)- Compound Quizalofop- 2ODAA gae?ha gai?ha Obs Exp AAcid p-ethyl IPOHE

32 O 45 gae/ha. gai?ha Obs Exp O 9.38 O 4.38 O O O 18.75 O 8.75 O 2O O 37.5 O 17.5 O 40 32 9.38 50 45 O 15 O 32 18.75 60 45 O 30 O 32 37.5 65 45 4.38 15 NT O 8.75 15 45 2O US 2014/003 1228A1 Jan. 30, 2014 28

TABLE 12-continued TABLE 14-continued Synergistic Activity of Foliar-Applied Compound A Acid and Quizalofop-p-ethyl Herbicidal Compositions on Control Synergistic Activity of Foliar-Applied Compound A Benzyl of Weeds Common to Rice Cropping Systems. Ester and Diclofop-methyl Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems. Visual Weed Control (%)- Compound Quizalofop- 2ODAA Visual Weed AAcid p-ethyl IPOHE Compound Control (%)- A Benzyl Diclofop- 22 DAA gae?ha gai?ha Obs Exp Ester methyl CYPIR

17.5 15 70 40 gae/ha. gai?ha Obs Exp 4.38 30 60 O 8.75 30 90 2O 17.5 30 70 40 O 28O O O S60 O O 1120 O 8 28O 30 2O TABLE 13 16 28O 1OO 85 Synergistic Activity of Foliar-Applied Compound A Benzyl 32 28O 1OO 100 Ester and Quizalofop-p-ethyl Herbicidal Compositions on 8 S60 35 2O Control of Weeds Common to Rice Cropping Systems. 16 S60 75 85 32 S60 1OO 100 Visual Weed Compound Control (%)- 8 1120 50 2O A Benzyl Quizalofop- 22 DAA 16 1120 1OO 85 Ester p-ethyl ECHCG 32 1120 1OO 100 gae?ha gai?ha Obs Exp

8 O 35 16 O 65 TABLE 1.5 32 O 8O O 3.75 2O Synergistic Activity of Foliar-Applied Compound O 7.5 30 AAcid and Profoxydim Herbicidal Compositions 8 3.75 85 48 on Weed Control in a Rice Cropping System. 16 3.75 65 72 32 3.75 85 84 Visual Weed 8 7.5 85 55 Control (%)- 16 7.5 100 76 Compound 2ODAA 32 7.5 100 86 AAcid Profoxydim ECHCO Visual Weed gae/ha. gai?ha Obs Exp Compound Control (%)- A Benzyl Quizalofop- 22 DAA 4.38 O 40 Ester p-ethyl IPOHE O 12.5 70 4.38 12.5 99 82 gae?ha gai?ha Obs Exp

32 O 45 O 1.88 O TABLE 16 O 3.75 O O 7.5 O Synergistic Activity of Foliar-Applied Compound 32 1.88 60 45 A Benzyl Ester and Profoxydim Herbicidal Compositions 32 3.75 60 45 32 7.5 50 45 on Weed Control in a Rice Cropping System. Visual Weed Comopund Control (%)- A Benzyl 2ODAA TABLE 1.4 Ester Profoxydim LEFCEH Synergistic Activity of Foliar-Applied Compound A Benzyl gae/ha. gai?ha Obs Exp Ester and Diclofop-methyl Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems. 4.38 O O 8.75 O 10 Visual Weed 17.5 O 25 Compound Control (%)- O 12.5 O A Benzyl Diclofop- 22 DAA O 25 40 Ester methyl CYPIR 4.38 12.5 10 O 8.75 12.5 30 10 gae?ha gai?ha Obs Exp 17.5 12.5 50 25 4.38 25 50 40 8 O 2O 8.75 25 50 46 16 O 85 17.5 25 70 55 32 O 100 US 2014/003 1228A1 Jan. 30, 2014 29

TABLE 17 TABLE 19 Synergistic Activity of Follar-Applied Compound A. Synergistic Activity of Foliar-Applied Compound A Benzyl Acid and Sethoxydim Herbicidal Compositions on Control Ester and Tralkoxydim Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems. of Weeds Common to Rice Cropping Systems. Compound Visual Weed Control (%) - 22 DAA AAcid Sethoxydim CYPES Visual Weed Compound Control (%)- gae/ha. gai?ha Obs Exp A Benzyl 22 DAA Ester Tralkoxydim CYPIR 4.38 O 50 8.75 O 75 gae/ha. gai?ha Obs Exp O 67.5 O O 135 O 8 O 2O '. 38 2. 5 s so 16 O 85 8.75 67.5 8O 75 32 O 1OO 4.38 135 70 50 O 1OO O 8.75 135 1OO 75 O 2OO O 4.38 270 1OO 50 8 1OO 2O 2O 8.75 270 70 75 16 1OO 1OO 85 32 1OO 90 100 Compound Visual Weed Control (%) - 22 DAA 8 2OO 1OO 2O 16 2OO 60 85 AAcid Sethoxydim CYPDI CYPIR SCPU 32 2OO 1OO 100 gae/ha. gai?ha Obs Exp Obs Exp Obs Exp

4.38 O 60 – 15 – 60 — O 67.5 O — O — O — TABLE 20 O 135 O — O — O — O 270 O O O Synergistic Activity of Follar-Applied Compound A Benzyl 4.38 67.5 100 60 8O 15 8O 60 Ester and Pinoxaden Herbicidal Compositions on Control 4.38 135 100 60 8O 15 85 60 of Weeds Common to Rice Cropping Systems. 4.38 270 90 60 60 15 70 60 Visual Weed Compound Control (%)- A Benzyl 21 DAA Ester Pinoxaden ECHCO TABLE 18 gae/ha. gai?ha Obs Exp Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Sethoxydim Herbicidal Compositions on Control 8 O 40 of Weeds Common to Rice Cropping Systems. 16 O 70 32 O 95 Visual Weed O 15 15 Compound Control (%)- O 30 85 A Benzyl 22 DAA O 60 95 Ester Sethoxydim ECHCG 8 15 75 49 16 15 85 75 gae?ha gai?ha Obs Exp 32 15 95 96 8 30 95 91 8 O 35 16 30 95 96 16 O 65 32 30 95 99 32 O 8O 8 60 1OO 97 O 56 30 16 60 1OO 99 O 112 90 32 60 1OO 100 8 56 90 55 16 56 99 76 Visual Weed 32 56 95 86 Compound Control (%)- 8 112 100 94 A Benzyl 21 DAA 16 112 99 97 Ester Pinoxaden IPOHE 32 112 100 98 gae/ha. gai?ha Obs Exp Visual Weed Compound Control (%)- 16 O 10 A Benzyl 22 DAA 32 O 25 Ester Sethoxydim LEFCEH O 15 10 O 30 10 gae?ha gai?ha Obs Exp O 60 O 16 15 2O 19 8 O 15 32 15 60 33 16 O 50 16 30 25 19 O 112 70 32 30 40 33 8 112 100 75 16 60 15 10 16 112 100 85 32 60 50 25 US 2014/003 1228A1 Jan. 30, 2014 30

TABLE 20-continued TABLE 21-continued Synergistic Activity of Foliar-Applied Compound A Benzyl Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Pinoxaden Herbicidal Compositions on Control Ester and Clethodim Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems. of Weeds Common to Rice Cropping Systems. 8 28O 1OO 70 Visual Weed 16 28O 85 85 Compound Control (%)- A Benzyl 21 DAA BRAPP Brachiaria platyphylla signalgrass, Ester Pinoxaden SCPU (Griseb.) Nash broadleaf CYPDI Cyperus diformis L. Sedge, Smallflower gae?ha gai?ha Obs Exp umbrella CYPES Cyperus esculentus L. nutsedge, yellow CYPIR Cyperus iria L. flatsedge, rice 8 O 85 DIGSA Digitaria sanguinalis (L.) Scop. crabgrass, large O 15 O ECHCG Echinochloa crusgalli (L.) Beauv. barnyardgrass O 30 O ECHCO Echinochloa colona (L.) Link junglerice O 60 O IPOHE Ipomoea hederacea Jacq. morningglory, 8 15 99 85 ivyleaf ISCRU Ischaemum rugosum Salisb. Saramollagrass 8 30 100 85 LEFCH Leptochloa chinensis (L.) Nees sprangletop, 8 60 100 85 Chinese SCPJU Schoenopiectus iuncoides bulrush, Japanese (Roxb.) Palla gae/ha = grams acid equivalent per hectare TABLE 21 gai?ha = grams active ingredient per hectare Obs = observed value Synergistic Activity of Foliar-Applied Compound A Benzyl Exp = expected value as calculated by Colby's equation Ester and Clethodim Herbicidal Compositions on Control DAA = days after application of Weeds Common to Rice Cropping Systems. NT = not tested Compound A Benzyl Visual Weed Control (%) - 20 DAA Example II Ester Clethodim BRAPP DIGSA Evaluation of In-Water Applied Herbicidal Mixtures gae/ha. gai?ha Obs Exp Obs Exp for Weed Control in Transplanted Paddy Rice 8 O 70 15 0176 Weed seeds or nutlets of the desired test plant spe 16 O 75 25 cies were planted in puddled soil (mud) prepared by mixing a 32 O 90 35 O 70 10 50 shredded, non-sterilized mineral soil (50.5 percent silt, 25.5 8 70 100 73 75 58 percent clay, and 24 percent sand, with a pH of about 7.6 and 16 70 100 78 8O 63 an organic matter content of about 2.9 percent) and water at a 32 70 100 91 85 68 1:1 volumetric ratio. The prepared mud was dispensed in 365 Visual Weed mL aliquots into 16-ounce (oZ.) non-perforated plastic pots Compound Control (%)- with a surface area of 86.59 square centimeters (cm) leaving A Benzyl 2ODAA a headspace of 3 centimeters (cm) in each pot. Mud was Ester Clethodim CYPES allowed to dry overnight prior to planting or transplanting. gae?ha gai?ha Obs Exp Rice seeds were planted in Sun Gro MetroMix R. 306 planting mixture, which typically has a pH of 6.0 to 6.8 and an organic 8 O O matter content of about 30 percent, in plastic plug trays. 16 O 75 O 70 O Seedlings at the second or third leaf stage of growth were O 140 O transplanted into 860 mL of mud contained in 32-oZ. non O 28O O perforated plastic pots with a surface area of 86.59 cm 4 days 8 70 60 O prior to herbicide application. The paddy was created by 16 70 85 75 8 140 8O O filling the headspace of the pots with 2.5 to 3 cm of water. 16 140 95 75 When required to ensure good germination and healthy 8 28O 95 O plants, a fungicide treatment and/or other chemical or physi 16 28O 90 75 cal treatment was applied. The plants were grown for 4-22 days in a greenhouse with an approximate 14 hr photoperiod Visual Weed Compound Control (%)- which was maintained at about 29C during the day and 26°C. A Benzyl 2ODAA during the night. Nutrients were added as Osmocote(R) (19:6: Ester Clethodim SCPU 12, N:P:K+minor nutrients) at 2 g per 16-oZ. pot and 4g per 32-oZ. pot. Water was added on a regular basis to maintain the gae?ha gai?ha Obs Exp paddy flood, and Supplemental lighting was provided with 8 O 70 overhead metal halide 1000-Watt lamps as necessary. The 16 O 85 plants were employed for testing when they reached the first O 140 O O 28O O through fourth true leaf stage. 8 140 100 70 0177 Treatments consisted of the acid or esters of 16 140 100 85 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-meth oxy-phenyl)pyridine-2-carboxylic acid (compound A) each US 2014/003 1228A1 Jan. 30, 2014

formulated as an SC (Suspension concentrate) and various stock solutions obtained can be diluted with an equivalent herbicidal components alone and in combination. Forms of Volume of an aqueous mixture containing 2.5% (v/v) crop oil compound A were applied on an acid equivalent basis. concentrate so that the final application Solutions contain Forms of compound A (compound of formula I) tested 1.25% (v/v) crop oil concentrate. include: 0182. Applications were made by injecting with a pipetter appropriate amounts of the application Solutions, individu ally and sequentially, into the aqueous layer of the paddy.

Compound A Control plants were treated in the same manner with the Solvent blank. Applications were made so that all treated plant material received the same concentrations of acetone and crop oil concentrate. 0183 The treated plants and control plants were placed in a greenhouse as described above and water was added as needed to maintain a paddy flood. After approximately 3 weeks the condition of the test plants as compared with that of the untreated plants was determined visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury or growth inhibition and 100 corresponds to complete kill. 0.184 Colby's equation was used to determine the herbi cidal effects expected from the mixtures (Colby, S. R. 1967. Compound A Calculation of the synergistic and antagonistic response of herbicide combinations. Weeds 15:20-22.). 0185. The following equation was used to calculate the expected activity of mixtures containing two active ingredi ents, A and B: Expected=A+B-(AxB/100) 0186 A observed efficacy of active ingredient A at the same concentration as used in the mixture. 0187 B-observed efficacy of active ingredient B at the same concentration as used in the mixture. Benzyl Ester 0188 Some of the compounds tested, application rates employed, plant species tested, and results are given in Tables 22-39. 0178. Other herbicidal components were applied on an acid equivalent (ae) or active ingredient (ai) basis as to normal TABLE 22 practice used in the market, and included acetyl CoA car boxylase (ACCase) inhibiting herbicides (cyclohexanedione Synergistic Activity of In-Water Applications of Compound and aryloxyphenoxypropionate chemical classes) cyhalofop AAcid and Cyhalofop-butyl Herbicidal Compositions butyl formulated as Clincher R. EC, fenoxaprop-p-ethyl on Weed Control in a Rice Cropping System. isoxadifen-ethyl formulated as RiceStar(RHT, fenoxaprop-p- Visual Weed Control (%)- ethyl-mefenpyr diethyl formulated as Puma 1EC, metamifop Compound Cyhalofop- 25 DAA formulated as Metamifop EC, haloxyfop-methyl formulated AAcid butyl ECHOR as Gallant SuperR), fluazifop-p-butyl formulated as Fusi lade(RDX, quizalofop-p-ethylformulated as Assure(RII, pro gae/ha. gai?ha Obs Exp foxydim formulated as Aura.R. 20EC, and sethoxydim formu 8.75 O O lated as Poast(R). 17.5 O O 0179 Treatment requirements for each compound or her 35 O 40 bicidal component were calculated based upon the rates being O 90 O 8.75 90 1OO O tested, the concentration of active ingredient or acid equiva 17.5 90 1OO O lent in the formulation, an application Volume of 2 mL per 35 90 1OO 40 component perpot, and an application area of 86.59 cm per pot. Visual Weed Control (%)- 0180 For formulated compounds, a measured amount Compound Cyhalofop- 25 DAA was placed in an individual 100 or 200 mL. glass vial and was AAcid butyl SCPU dissolved in a volume of 1.25% (v/v) Agri-Dex(R) crop oil concentrate to obtain application Solutions. If the test com gae/ha. gai?ha Obs Exp pound did not dissolve readily, the mixture was warmed and/ 8.75 O 65 or Sonicated. 17.5 O 8O 0181 For technical grade compounds, a weighed amount 35 O 95 O 90 O can be placed in an individual 100 to 200 mL. glass vial and O 18O O dissolved in a Volume of acetone to obtain concentrated Stock 8.75 90 95 65 solutions. If the test compound does not dissolve readily, the 17.5 90 95 8O mixture can be warmed and/or Sonicated. The concentrated US 2014/003 1228A1 Jan. 30, 2014 32

TABLE 22-continued TABLE 24-continued Synergistic Activity of In-Water Applications of Compound Synergistic Activity of In-Water Applications of Compound AAcid and Cyhalofop-butyl Herbicidal Compositions AAcid and Fenoxaprop-p-ethyl + Isoxadifen-ethyl Herbicidal on Weed Control in a Rice Cropping System. Compositions on Weed Control in a Rice Cropping System. 35 90 100 95 8.75 18O 95 65 17.5 70 50 55 17.5 18O 95 8O 35 70 1OO 58 35 18O 95 95 Fenoxaprop Visual Weed Visual Weed p-ethyl + Control (%)- Control (%)- Compound Isoxadifen 21 DAA Compound Cyhalofop- 19 DAA AAcid butyl LEFCEH AAcid ethyl FIMMI gae?ha gai?ha Obs Exp gae/ha. Obs Exp

42.4 O 10 8.75 O 2O O 18O 75 O 35 O 42.4 18O 90 78 O 70 O 8.75 35 1OO 2O 8.75 70 60 2O

Fenoxaprop Visual Weed TABLE 23 p-ethyl + Control (%)- Compound Isoxadifen 21 DAA Synergistic Activity of In-Water Applications of Compound AAcid ethyl SCPU A Benzyl Ester and Cyhalofop-butyl Herbicidal Compositions on Weed Control in a Rice Cropping System. gae/ha. Obs Exp Visual Weed Compound Control (%)- 8.75 65 A Benzyl Cyhalofop- 25 DAA 17.5 90 Ester butyl ECHOR O 35 O O 70 O gae?ha gai?ha Obs Exp 8.75 35 8O 65 8.75 O 85 17.5 35 99 90 17.5 O 90 8.75 70 85 65 35 O 100 17.5 70 95 90 O 90 O 8.75 90 100 85 17.5 90 100 90 35 90 100 100 TABLE 25 Visual Weed Compound Control (%)- Synergistic Activity of In-Water Applications of Compound A A Benzyl Cyhalofop- 19 DAA Benzyl Ester and Fenoxaprop-p-ethyl + Isoxadifen-ethyl Ester butyl SCPMA Herbicidal Compositions on Weed Control in a Rice Cropping System. Fenoxaprop Visual Weed gae?ha gai?ha Obs Exp Compound p-ethyl + Control (%)- A Benzyl Isoxadifen 21 DAA 35 O O Ester ethyl ECHOR O 18O O 35 18O 50 O gae/ha. Obs Exp

4.38 O O 8.75 O 10 TABLE 24 17.5 O 60 O 70 50 Synergistic Activity of In-Water Applications of Compound 4.38 70 1OO 50 AAcid and Fenoxaprop-p-ethyl + Isoxadifen-ethyl Herbicidal 8.75 70 1OO 55 Compositions on Weed Control in a Rice Cropping System. 17.5 70 1OO 8O Fenoxaprop- Visual Weed Fenoxaprop Visual Weed p-ethyl + Control (%)- Compound p-ethyl + Control (%)- Compound Isoxadifen- 21 DAA A Benzyl Isoxadifen 21 DAA AAcid ethyl ECHOR Ester ethyl CYPRO gae?ha gai?ha Obs Exp gae/ha. Obs Exp

8.75 O O 4.38 O 2O 17.5 O 10 O 35 O 35 O 15 O 70 O O 70 50 4.38 35 99 2O 8.75 70 100 50 4.38 70 50 2O US 2014/003 1228A1 Jan. 30, 2014 33

TABLE 26 TABLE 29 Synergistic Activity of In-Water Applications of Compound Synergistic Activity of In-Water Applications of Compound AAcid A Benzyl Ester and Haloxyfop-methyl Herbicidal Compositions and Fenoxaprop-p-ethyl + Mefenpyr-diethyl Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems on Control of Weeds Common to Rice Cropping Systems. Visual Weed Fenoxaprop- Visual Weed Compound Control (%)- A Benzyl Haloxyfop- 2ODAA p-ethyl + Control (%)- Ester methyl CYPRO Compound Mefenpyr 21 DAA AAcid diethyl ECHOR gae/ha. gai?ha Obs Exp

gae?ha gai?ha Obs Exp 4.38 O 50 8.75 O 1OO 17.5 O 1OO 10.6 O O 13.5 O 21.2 O 15 O 27 O 42.4 O 15 4.38 13.5 75 50 O 23 O 8.75 13.5 95 100 10.6 23 25 O 17.5 13.5 1OO 100 4.38 27 8O 50 21.2 23 15 15 8.75 27 95 100 42.4 23 40 15 17.5 27 1OO 100

TABLE 27 TABLE 30 Synergistic Activity of In-Water Applications of Synergistic Activity of In-Water Applications of Compound A Benzyl Ester and Fenoxaprop-p-ethyl + Compound A Acid and Metamifop Herbicidal Compositions Mefenpyr-diethyl Herbicidal Compositions on On Weed Control in a Rice Cropping System. Control of Weeds Common to Rice Cropping Systems. Compound Visual Weed Control (%) - 21 DAA Fenoxaprop- Visual Weed Compound p-ethyl + Control (%)- AAcid Metamifop FIMMI SCPMA A Benzyl Mefenpyr- 21 DAA Ester diethyl ECHOR gae/ha. gai?ha Obs Exp Obs Exp gae?ha gai?ha Obs Exp 35 O 85 O O 75 O O 8 O 10 O 150 O O 16 O 25 35 75 100 85 60 O 32 O 35 35 150 100 85 50 O O 23 15 8 23 100 24 16 23 2O 36 32 23 75 45 TABLE 31 Synergistic Activity of In-Water Applications of Compound A Benzyl Ester and Metamifop Herbicidal Compositions TABLE 28 on Weed Control in a Rice Cropping System. Synergistic Activity of In-Water Applications of Compound Visual Weed AAcid and Haloxyfop-methyl Herbicidal Compositions on Compound Control (%)- Control of Weeds Common to Rice Cropping Systems. A Benzyl 21 DAA Ester Metamifop SCPU Visual Weed Control (%)- gae/ha. gai?ha Obs Exp Compound Haloxyfop- 2ODAA AAcid methyl SCPU 4.38 O 70 O 75 O gae?ha gai?ha Obs Exp O 150 O 4.38 75 99 70 8.75 O 70 4.38 150 1OO 70 17.5 O 95 35 O 95 Visual Weed O 13.5 O Compound Control (%)- O 27 O A Benzyl 21 DAA 8.75 13.5 90 70 Ester Metamifop ECHOR 17.5 13.5 95 95 35 13.5 95 95 gae/ha. gai?ha Obs Exp 8.75 27 95 70 17.5 27 100 95 48 O 78 35 27 100 95 96 O O 50 US 2014/003 1228A1 Jan. 30, 2014 34

TABLE 31-continued TABLE 34

Synergistic Activity of In-Water Applications of Compound Synergistic Activity of In-Water Applications of Compound A Benzyl Ester and Metamifop Herbicidal Compositions AAcid and Quizalofop-p-ethyl Herbicidal Compositions on on Weed Control in a Rice Cropping System. Control of Weeds Common to Rice Cropping Systems.

48 50 75 82 Visual Weed 96 50 100 84 Control (%)- Compound Quizalofop- 21 DAA AAcid p-ethyl ECHOR

TABLE 32 gae/ha. gai?ha Obs Exp Synergistic Activity of In-Water Applications of Compound AAcid and Fluazifop-p-butyl Herbicidal Compositions 17.5 O 25 on Control of Weeds Common to Rice Cropping Systems. 35 O 30 Visual Weed O 15 O Control (%)- Compound Fluazifop 21 DAA O 30 60 AAcid P-butyl ECHOR 17.5 15 50 25 gae/ha. Obs Exp 35 15 50 30 17.5 30 60 70 8.75 O 10 17.5 O 15 35 30 1OO 72 35 O 2O O 90 25 8.75 90 45 33 Visual Weed 17.5 90 15 36 35 90 100 40 Control (%)- Compound Quizalofop- 21 DAA Visual Weed AAcid p-ethyl CYPRO Control (%)- Compound Fluazifop 21 DAA AAcid P-butyl CYPRO gae/ha. gai?ha Obs Exp gae/ha. Obs Exp 8.75 O O 8.75 O 17.5 30 O 15 O 35 . 85 O 30 O O 90 O O 18O O 8.75 15 2O O 8.75 90 70 O 8.75 30 2O O 17.5 90 30 30 35 90 95 85 8.75 18O 2O O 17.5 18O 2O 30 35 18O 90 85 TABLE 35 Synergistic Activity of In-Water Applications of Compound A Benzyl Ester and Quizalofop-p-ethyl Herbicidal Compositions TABLE 33 on Control of Weeds Common to Rice Cropping Systems. Compound Synergistic Activity of In-Water Applications of Compound A Benzyl Quizalofop- Visual Weed Control (%) - 21 DAA A Benzyl Ester and Fluazifop-p-butyl Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems. Ester p-ethyl ECHCG ECHOR Visual Weed gae/ha. gai?ha Obs Exp Obs Exp Compound Control (%)- A Benzyl Fluazifop 21 DAA 4.38 O 15 O Ester P-butyl ECHOR 8.75 O 2O 15 17.5 O 75 10 Obs Exp O 15 50 O O 30 100 60 8 O 8 4.38 15 100 58 60 O 16 O 5 8.75 15 100 60 30 15 32 O 13 17.5 15 100 88 50 10 O 45 O 4.38 30 100 100 100 60 8 45 O 8.75 30 100 100 100 66 16 45 15 17.5 30 100 100 100 64 32 45 30 1 US 2014/003 1228A1 Jan. 30, 2014 35

TABLE 36 TABLE 37-continued Synergistic Activity of In-Water Applications of Compound AAcid and Profoxydim Herbicidal Compositions on Control Synergistic Activity of In-Water Applications of Compound of Weeds Common to Rice Cropping Systems. A Benzyl Ester and Profoxydim Herbicidal Compositions on Visual Weed Control of Weeds Common to Rice Cropping Systems. Control (%)- Compound 21 DAA AAcid Profoxydim LEFCEH O 50 30 gae?ha gai?ha Obs Exp 8 50 1OO 65 16 50 1OO 72 17.5 O O 32 50 1OO 99 35 O 2O O 25 85 17.5 25 100 85 35 25 100 88 TABLE 38 Visual Weed Control (%)- Compound 22 DAA Synergistic Activity of In-Water Applications of Compound AAcid Profoxydim ECHCG AAcid and Sethoxydim Herbicidal Compositions on Control gae?ha gai?ha Obs Exp of Weeds Common to Rice Cropping Systems.

16 O 2O Visual Weed 32 O 25 O 50 30 Control (%)- 16 50 70 44 Compound 21 DAA 32 50 100 48 AAcid Sethoxydim FIMMI

Visual Weed gae/ha. gai?ha Obs Exp Control (%)- Compound 22 DAA AAcid Profoxydim SCPU 8.75 O 2O O 135 50 gae?ha gai?ha Obs Exp O 270 30 16 O 70 8.75 135 1OO 60 O 50 O 8.75 270 1OO 44 O 1OO O 16 50 95 70 16 1OO 100 70 Visual Weed Control (%)- Compound 21 DAA AAcid Sethoxydim SCPU TABLE 37 Synergistic Activity of In-Water Applications of Compound gae/ha. gai?ha Obs Exp A Benzyl Ester and Profoxydim Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems. 8.75 O 65 Visual Weed 17.5 O 90 Compound Control (%)- A Benzyl 21 DAA O 135 O Ester Profoxydim ECHOR 8.75 135 95 65 gae?ha gai?ha Obs Exp 17.5 135 1OO 90

4.38 O O 8.75 O 15 17.5 O 10 TABLE 39 O 25 O 4.38 25 30 O Synergistic Activity of In-Water Applications of Compound 8.75 25 100 15 A Benzyl Ester and Sethoxydim Herbicidal Compositions on 17.5 25 100 10 Control of Weeds Common to Rice Cropping Systems. Visual Weed Visual Weed Compound Control (%)- Compound Control (%)- A Benzyl 22 DAA A Benzyl 21 DAA Ester Profoxydim ECHCG Ester Sethoxydim ECHCG gae?ha gai?ha Obs Exp gae/ha. gai?ha Obs Exp

8 O 50 4.38 O 15 16 O 60 8.75 O 60 32 O 99 O 135 60 US 2014/003 1228A1 Jan. 30, 2014 36

TABLE 39-continued Forms of compound A (compound of formula I) tested include: Synergistic Activity of In-Water Applications of Compound A Benzyl Ester and Sethoxydim Herbicidal Compositions on Compound A Control of Weeds Common to Rice Cropping Systems.

4.38 135 75 66 8.75 135 100 84

CYPRO Cyperus rotundus L. nutsedge, purple ECHCG Echinochloa crusgali (L.) Beauv. barnyardgrass ECHOR Echinochloa oryzoides (Ard.) Fritsch watergrass, early FIMMI Fimbristylis miliacea (L.) Vahl fringerush, globe LEFCH Leptochloa chinensis (L.) Nees sprangletop, Chinese SCPJU Schoenopiectus iuncoides (Roxb.) Palla bulrush, Japanese

SCPMA Bolboschoenus maritimus (L.) Palla or Compound A Schoenopiectus maritimus (L.) Lye clubrush, Sea gae/ha = grams acid equivalent per hectare gai?ha = grams active ingredient per hectare Obs = observed value Exp = expected value as calculated by Colby's equation DAA = days after application

Example III

Evaluation of Postemergence Foliar-Applied Benzyl Ester Herbicidal Mixtures for Control of Weeds Common to Row Crops such as Corn and Soybeans 0.192 Other herbicidal components were applied on an acid equivalent basis and included acetyl coA carboxylase 0189 Seeds or nutlets of the desired test plant species (ACCase)-inhibiting herbicide (cyclohexanedione and ary were planted in a Soil matrix prepared by mixing a loam or loxyphenoxypropionate chemical classes) quizalofop-p- sandy loam Soil (e.g., 28.6 percent silt, 18.8 percent clay, and ethyl formulated as Assure(R) II. 52.6 percent sand, with a pH of about 5.8 and an organic matter content of about 1.8 percent) and calcareous grit in an 0193 For treatments comprised of formulated com 80 to 20 ratio. The soil matrix was contained in plastic pots pounds, measured amounts of compounds were placed indi vidually in 25 mL glass vials and diluted in a volume of 1.5% with a surface area of 84.6 square centimeters (cm) and a (v/v) Agri-Dex(R) crop oil concentrated to obtain 6x stock volume of 560 cubic centimeters (cm). When required to Solutions. If a test compound did not dissolve readily, the ensure good germination and healthy plants, a fungicide treat mixture was warmed and/or Sonicated. Application solutions ment and/or other chemical or physical treatment was were prepared by adding an appropriate amount of each stock applied. The plants were grown for 7-31 days (d) in a green Solution (typically 2 mL) and diluted to the appropriate final house with an approximate 15 hour (h) photoperiod which concentrations with the addition of an appropriate amount of was maintained at about 23-29° C. during the day and 22-28° 1.5% (v/v) crop oil concentrate and an appropriate amount of C. during the night. Nutrients (Peters Excel(R) 15-5-15 5-Ca water so that the final spray solutions contained 1.25+/-0. 2-Mg) and water were added on a regular basis and Supple 05% (v/v) crop oil concentrate. mental lighting was provided with overhead metal halide 0194 For treatments comprised of technical compounds, 1000-Watt lamps as necessary. The plants were employed for weighed amounts can be placed individually in 25 mL glass testing when they reached the first, second, or third true leaf vials and dissolved in a volume of 97:3 V/vacetone/DMSO to Stage. obtain 12x Stock solutions. If a test compound does not dis 0190. Treatment requirements were calculated based upon Solve readily, the mixture can be warmed and/or Sonicated. the rates being tested, the concentration of active ingredientor Application Solutions can be prepared by adding an appro acid equivalent in the formulation, and a 12 mL application priate amount of each stock solution (e.g., 1 mL) and diluted Volume at a rate of 187 L/ha. to the appropriate final concentrations with the addition of an appropriate amount of 1.5% (v/v) crop oil concentrate and an 0191 Treatments consisted of the acid or esters of appropriate amount of water so that the final spray solutions 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-meth contain 1.25% (v/v) crop oil concentrate. When technical oxy-phenyl)pyridine-2-carboxylic acid (Compound A), each materials are used, the concentrated Stock solutions can be formulated as an SC (Suspension concentrate), and various added to the spray solutions so that the final acetone and herbicidal components alone and in combination. Forms of DMSO concentrations of the application solutions are 16.2% compound A were applied on an acid equivalent basis. and 0.5%, respectively. US 2014/003 1228A1 Jan. 30, 2014 37

0.195 For treatments comprised of formulated and techni TABLE 40 cal compounds, weighed amounts of the technical materials Synergistic Activity of Foliar-Applied Compound can be placed individually in 25 mL glass vials and dissolved AAcid and Quizalofop-p-ethyl Herbicidal Compositions in a volume of 97.3 V/v acetone/DMSO to obtain 6x stock on Control of Weeds Common to Row Crops Such as Solutions, and measured amounts of the formulated com Corn and Soybean Cropping Systems. pounds can be placed individually in 25 mL glass vials and Visual Weed Control (%)- diluted in a volume of 1.5% (v/v) crop oil concentrate or water Compound Quizalofop 14 DAA to obtain 6x stock Solutions. If a test compound does not AAcid p-ethyl AVEFA dissolve readily, the mixture can be warmed and/or Sonicated. gae/ha. gae/ha. Obs Exp Application Solutions can be prepared by adding an appro 3.75 O O priate amount of each stock solution (e.g., 2 mL) and diluted 7.5 O O to the appropriate final concentrations with the addition of an 15 O O appropriate amount of an aqueous mixture of 1.5% (v/v) crop O 14.25 40 3.75 14.25 85 40 oil concentrate so that the final spray solutions contained 7.5 14.25 70 40 1.25% (v/v) crop oil concentrate. When required, additional 15 14.25 55 40 water and/or 97:3 V/v acetone/DMSO can be added to indi Visual Weed vidual application solutions so that the final acetone and Control (%)- Compound Quizalofop 14 DAA DMSO concentrations of the application solutions being AAcid p-ethyl LOLMU compared are 16.2% and 0.5%, respectively. gae/ha. gae/ha. Obs Exp 0196. All stock solutions and applications solutions were visually inspected for compound compatibility prior to appli 3.75 O O cation. Compound requirements are based upon a 12 mL 7.5 O 10 15 O 10 application volume at a rate of 187 liters per hectare (L/ha). O 3.56 O Formulated compounds were applied to the plant material O 7.125 60 3.75 3.56 50 O with an overhead Mandel track sprayer equipped with 8002E 7.5 3.56 30 1O nozzles calibrated to deliver 187L/ha over an application area 15 3.56 40 10 of 0.503 square meters (m) at a spray height of 18 to 20 3.75 7.125 70 60 7.5 7.125 8O 64 inches (46 to 50 cm) above the average plant canopy height. 15 7.125 70 64 Control plants were sprayed in the same manner with the solvent blank. 0197) The treated plants and control plants were placed in TABLE 41 a greenhouse as described above and watered by Sub-irriga Synergistic Activity of Foliar-Applied Compound A Benzyl Ester tion to prevent wash-off of the test compounds. After approxi and Quizalofop-p-ethyl Herbicidal Compositions on Weeds Common mately 2 weeks, the condition of the test plants as compared to Row Crops Such as Corn and Soybean Cropping Systems. with that of the untreated plants was determined visually and Visual Weed scored on a scale of 0 to 100 percent where 0 corresponds to Compound Control (%)- A Benzyl Quizalofop 14 DAA no injury or growth inhibition and 100 corresponds to com Ester p-ethyl AVEFA plete kill. gae/ha. gae/ha. Obs Exp 0198 Colby's equation was used to determine the herbi 3.75 O 10 cidal effects expected from the mixtures (Colby, S.R. 1967. 7.5 O O Calculation of the synergistic and antagonistic response of 15 O 10 O 14.25 40 herbicide combinations. Weeds 15:20-22.). 3.75 14.25 75 46 0199 The following equation was used to calculate the 7.5 14.25 99 40 expected activity of mixtures containing two active ingredi 15 14.25 40 46 ents, A and B: Visual Weed Compound Control (%)- Expected=A+B-(AxB/100) A Benzyl Quizalofop 14 DAA Ester p-ethyl LOLMU 0200 A observed efficacy of active ingredient A at the gae/ha. gae/ha. Obs Exp same concentration as used in the mixture. 3.75 O O 0201 B-observed efficacy of active ingredient B at the 7.5 O 10 same concentration as used in the mixture. 15 O 10 O 3.56 O O 7.125 60 0202 Some of the compounds tested, application rates 3.75 3.56 60 O employed, plant species tested, and results are given in Tables 7.5 3.56 40 10 40-41. US 2014/003 1228A1 Jan. 30, 2014 38

TABLE 41-continued 0206 Measured aliquots of benzyl ester of 4-amino-3- chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxy-phenyl) Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Quizalofop-p-ethyl Herbicidal Compositions on Weeds Common pyridine-2-carboxylic acid (Compound A) were placed in 25 to Row Crops Such as Corn and Soybean Cropping Systems. milliliter (mL) glass vials and diluted in a volume of 1.25% (v/v) Agri-Dex(R) crop oil concentrate to obtain stock solu 15 3.56 35 10 3.75 7.125 70 60 tions. Compound requirements are based upon a 12 mL appli 7.5 7.125 75 64 cation volume at a rate of 187 liters per hectare (L/ha). Spray 15 7.125 8O 64 solutions of the second cereal herbicide and experimental AVEFA Avenafatua L. oat, wild compound mixtures were prepared by adding the Stock solu LOLMU. Lolium multiflorum Lam. ryegrass, Italian tions to the appropriate amount of dilution solution to form 12 gae/ha = grams acid equivalent per hectare mL spray Solution with active ingredients in two- and three gai?ha = grams active ingredient per hectare Obs = observed value way combinations. Formulated compounds were applied to Exp = expected value as calculated by Colby's equation the plant material with an overhead Mandel track sprayer DAA = days after application equipped with an 8002E nozzle calibrated to deliver 187 L/ha overan application area of 0.503 square meters (m)ata spray height of 18 inches (4.6 cm) above average plant canopy. Example IV Control plants were sprayed in the same manner with the solvent blank. Evaluation of Postemergence Herbicidal Activity of 0207. The treated plants and control plants were placed in Mixtures in Cereal Crops in the Greenhouse a greenhouse as described above and watered by Sub-irriga 0203. Seeds of the desired test plant species were planted tion to prevent wash-off of the test compounds. After 20-22 in Sun Gro MetroMix 306 planting mixture, which typically days, the condition of the test plants as compared with that of has a pH of 6.0 to 6.8 and an organic matter content of about the control plants was determined visually and scored on a 30 percent, in plastic pots with a surface area of 103.2 square scale of 0 to 100 percent where 0 corresponds to no injury and centimeters (cm). When required to ensure good germina 100 corresponds to complete kill. tion and healthy plants, a fungicide treatment and/or other 0208 Colby's equation was used to determine the herbi chemical or physical treatment was applied. The plants were cidal effects expected from the mixtures (Colby, S. R. 1967. grown for 7-36 days in a greenhouse with an approximate 14 Calculation of the synergistic and antagonistic response of hour photoperiod which was maintained at about 18°C. dur ing the day and about 17°C. during the night. Nutrients and herbicide combinations. Weeds 15:20-22.). water were added on a regular basis and Supplemental light 0209. The following equation was used to calculate the ing was provided with overhead metal halide 1000-Watt expected activity of mixtures containing two active ingredi lamps as necessary. The plants were employed for testing ents, A and B: when they reached the second or third true leaf stage. Expected=A+B-(AxB/100) 0204 Treatments consisted of the benzyl ester of 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-meth 0210 A observed efficacy of active ingredient A at the oxy-phenyl)pyridine-2-carboxylic acid (Compound A), for same concentration as used in the mixture. mulated as an SC, a second cereal herbicide alone and then both in combination. 0211 B-observed efficacy of active ingredient B at the same concentration as used in the mixture. Forms of compound A (compound of formula I) tested include: The compounds tested, application rates employed, plant spe cies tested, and results are given in Tables 42-45.

Compound A TABLE 42 Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Clodinafop-propargyl Herbicidal Compositions on Weed Control in a Cereals Cropping System. Compound A Benzyl Clodinofop- Visual Weed Control (%) - 21 DAA Ester propargyl LOLMU KCHSC gai?ha gai?ha Obs Exp Obs Exp

5 O O 2O 10 O O 30 Benzyl Ester O 15 60 O O 30 48 10 5 15 60 60 70 2O 10 15 65 60 8O 30 0205. Other herbicidal components were applied on an 5 30 73 48 70 28 active ingredient basis and included acetyl-CoA carboxylase 10 30 78 48 8O 37 (ACCase)-inhibiting herbicides clodinafop-propargyl. fenoxaprop-P-ethyl, pinoxaden and tralkoxydim. US 2014/003 1228A1 Jan. 30, 2014 39

TABLE 42-continued TABLE 45 Synergistic Activity of Foliar-Applied Compound A Synergistic Activity of Foliar-Applied Compound A Benzyl Benzyl Ester and Tralkoxydim Herbicidal Compositions Ester and Clodinafop-propargyl Herbicidal Compositions on Weed Control in a Cereals Cropping System. on Weed Control in a Cereals Cropping System. Compound A Benzyl Visual Weed Control (%) - 21 DAA Compound Ester Tralkoxydim AVEFA LOLMU KCHSC A Benzyl Clodinofop- Visual Weed Control (%) - 21 DAA gai?ha gai?ha Obs Exp Obs Exp Obs Exp Ester propargyl PHAMI APESV ALOMY 5 O O O 2O 10 O O O 30 gai?ha gai?ha Obs Exp Obs Exp Obs Exp O 50 78 86 10 O 100 99 96 O 5 50 95 78 95 86 55 28 5 O O O O 10 50 96 78 94 86 65 37 5 100 97 99 97 96 65 2O 10 O O O O 10 100 97 99 95 96 73 30 O 15 48 15 8O ALOMY Alopecurus myosuroides Huds. blackgrass O 30 55 68 82 APESV Apera spica-venti (L.) Beauv. windgrass 5 15 73 48 55 15 90 8O AVEFA Avena fatua L. wild oat 10 15 73 48 55 15 88 8O KCHSC Kochia scoparia (L.) Schrad. kochia LOLMU. Lolium multiflorum Lam. ryegrass, Italian 5 30 55 55 78 68 94 82 PHAMI Phaiaris minor Retz. Canarygrass, littleseed 10 30 45 55 8O 68 87 82 gae/ha = grams acid equivalent per hectare gai?ha = grams active ingredient per hectare Obs = observed value Exp = expected value as calculated by Colby's equation DAA = days after application TABLE 43 Synergistic Activity of Foliar-Applied Compound A Benzyl Example V Ester and Fenoxaprop-P-ethyl Herbicidal Compositions on Weed Control in a Cereals Cropping System. Evaluation of Post-Emergence Herbicidal Activity of Compound Mixtures Applied Under Field Conditions to Seeded A Benzyl Fenoxaprop- Visual Weed Control (%) - 21 DAA Rice Ester P-ethyl KCHSC PHAMI APESV 0212 Multiple field trials were conducted under commer cial grower field conditions in Tolima, Colombia; Thessal gai?ha gai?ha Obs Exp Obs Exp Obs Exp oniki, Greece; Bianze and Copiano, Italy; and Humphrey, 5 O 2O O O Ark., USA. Trials sites were located in commercially grown 10 O 30 O O fields of direct-seeded rice (Oryza sativa) using standard O 23 O 10 50 herbicide small plot research methodology. Plots varied from O 46 O 45 83 5 23 60 2O 10 10 65 50 2 to 3 meter (m)x5 to 8 m (width}xlength) with 4 replicates per 10 23 68 30 10 10 63 50 treatment. The rice crop was grown using normal cultural 5 46 70 2O 55 45 81 83 practices for fertilization, seeding, watering, flooding and 10 46 70 30 55 45 83 83 maintenance to ensure good growth of the crop and the weeds. 0213 All treatments in the field trials were applied using a backpack compressed air/gas sprayer with flat fan nozzles TABLE 44 (80° or 110°) calibrated to apply 187 to 300 L/ha spray volume at approximately 200-400 kPa nozzle pressure. Com Synergistic Activity of Foliar-Applied Compound A mercially available products of cyhalofop-butyl (Clincher Benzyl Ester and Pinoxaden Herbicidal Compositions 180EC, Clincher 200EC, and Clincher SF (285 grai/L EC)) on Weed Control in a Cereals Cropping System. were mixed in water at appropriate formulated product rates Compound to achieve the desired rates based on a unit area of application A Benzyl Visual Weed Control (%) - 21 DAA (hectare) to achieve the desired rates as shown. Treatments were rate at 19 to 58 days after application (DAA) as com Ester Pinoxaden KCHSC PHAMI pared to the untreated control plants. Visual weed control was gai?ha gai?ha Obs Exp Obs Exp scored on a scale of 0 to 100 percent where 0 corresponds to no injury and 100 corresponds to complete kill. 5 O 2O O 10 O 30 O 0214 All treatment results, both for the single product and O 15 O 78 mixtures, are an average of 4 replicates. The trial sites had O 30 15 94 naturally occurring populations of weeds. The weed spectrum 5 15 75 2O 88 78 included, but was not limited to, rice flatsedge (Cyperus iria, 10 15 75 30 87 78 5 30 75 32 94 94 CYPIR); smallflower umbrellaplant (Cyperus diformis, 10 30 78 41 94 94 CYPDI), junglerice (Echinochloa colona, ECHCO), barn yardgrass (Echinochloa crus-galli, ECHCG); multiple Echi nochloa species in the same field (ECHSS), grasslike fimbri US 2014/003 1228A1 Jan. 30, 2014 40 stylis (Fimbristylis miliacea, FIMMI); ricefield bulrush Example V (Schoenoplectus mucronatus, SCPMU) and hemp Sesbania (Sesbania exaltata, SEBEX). All synergistic interactions Evaluation of Postemergence Foliar-Applied Ternary were significant at the P-0.01 level. Herbicidal Mixtures for Weed Control in Direct 0215. Some of the compounds tested, application rates Seeded Rice employed, plant species tested, and results are given in Tables 0216 Seeds or nutlets of the desired test plant species 46-48. were planted in a soil matrix prepared by mixing a sandy loam or loam soil (e.g., 32 percent silt, 23 percent clay, and 45 TABLE 46 percent sand, with a pH of about 6.5 and an organic matter content of about 1.9 percent) and calcareous grit in an 80 to 20 Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Cyhalofop-butyl Herbicidal Compositions on Weed ratio. The soil matrix was contained in plastic pots with a Control in a Rice Cropping System when evaluated 19 DAA Volume of 1 quart and a surface area of 83.6 square centime Days After Application) in Tolina, Colombia. ters (cm). When required to ensure good germination and healthy plants, a fungicide treatment and/or other chemical or Compound Cyhal physical treatment was applied. The plants were grown for A Benzyl ofop- Visual Weed Control (%) - 19 DAA 8-22 days in a greenhouse with an approximate 14 hr photo Ester butyl CYPIR ECHCO FIMMI period which was maintained at about 29° C. during the day and 26°C. during the night. Nutrients (Peters Excel(R) 15-5-15 gae/ha. gai?ha Obs Exp Obs Exp Obs Exp 5-Ca 2-Mg and iron chelate) were applied in the irrigation 12 O 69 76 Solution as needed and water was added on a regular basis. O 28O O O Supplemental lighting was provided with overhead metal 12 28O 85 69 90 76 halide 1000-Watt lamps as necessary. The plants were 24 O 39 employed for testing when they reached the first through O 190 16 fourth true leaf stage. 24 190 63 48 0217 Treatments consisted of the benzyl ester of 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-meth oxy-phenyl)pyridine-2-carboxylic acid (Compound A), for TABLE 47 mulated as an SC (Suspension concentrate), an ACCase inhibitor, and a third herbicidal component, each applied Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Cyhalofop-butyl Herbicidal Compositions on Weed alone and in ternary combination. Forms of compound A Control in a Rice Cropping System when evaluated 7 DAA (Days were applied on an acid equivalent basis. After Application) in Humphrew, Arkansas, USA. Forms of compound A (compound of formula I) tested include: Visual Weed Compound Control (%)- A Benzyl Cyhalofop- 7 DAA

Ester butyl SEBEX Compound A gaeha gai?ha Obs Exp 24 O 8O O 28O O 24 28O 90 8O 32 O 78 O 28O O 32 28O 93 78

TABLE 48 Synergistic Activity of Foliar-Applied Compound A Benzyl Benzyl Ester Ester and Cyhalofop-butyl Herbicidal Compositions on Weed Control in a Rice Cropping System when evaluated 55 to 58 DAA (Days After Application) in Greece (CYPDI 0218. The ACCase inhibitor component was applied on an and ECHCG) and Italy (ECHSS and SCPMU). active ingredient basis and included cyhalofop-R-butyl for Com- Cy mulated as Clincher(R) SF, fenoxaprop-p-ethyl formulated as pound hal- Visual Weed Control RiceStar R HT, and profoxydim formulated as Aura.R. 20EC. A. ofop- %) - SS-58DAA Otherherbicidal components were applied on an active ingre dient or acid equivalent basis depending on the compound Benzyl butyl and included penoxsulam formulated as GraspR SC, benta Ester gaif CYPDI ECHCG ECHSS SCPMU Zon Sodium formulated as Basagran triclopyr trimethylam gae/ha ha Obs Exp Obs Exp Obs Exp Obs Exp monium (TEA) salt formulated as Grandstand(R) R, bispyri 24 O 81 6 40 27 bac sodium formulated as Regiment(R) 80WP, imazamox O 300 O 29 37 6 ammonium formulated as BeyondR, benzobicyclon, quin 24 300 90 81 60 33 89 62 56 27 clorac formulated as Facet(R) 75DF, glyphosate dimethylam monium (DMA) salt formulated as Durango(R DMA, glufo sinate ammonium formulated as IgniteR 280, fentraZamide US 2014/003 1228A1 Jan. 30, 2014

formulated as an emSulsifiable concentrate (EC), propyrisul 0228 C-observed efficacy of active ingredient C at the furon formulated as Zeta One(R), and indanofan (technical same concentration as used in the mixture. grade material). 0219 Treatment requirements were calculated based upon 0229. The compounds tested, application rates employed, the rates being tested, the concentration of active ingredientor plant species tested, and results are given in Tables 49-62. acid equivalent in the formulation, and a 12 mL application Volume at a rate of 187 L/ha. TABLE 49 0220. For treatments comprised of formulated com Synergistic Activity of Foliar-Applied Compound A Benzyl pounds, measured amounts of compounds were placed indi Ester, Cyhalofop-Butyl, and PenoxSulam Ternary Herbicidal vidually in 25 mL glass vials and diluted in a volume of 1.25% Compositions on Weed Control in a Rice Cropping System. (v/v) Agri-Dex(R) crop oil concentrate to obtain 12x stock Solutions. If a test compound did not dissolve readily, the Visual Weed mixture was warmed and/or Sonicated. Application solutions Compound Control (%)- were prepared by adding an appropriate amount of each stock A Benzyl Cyhalofop- 21 DAA Solution (e.g., 1 mL) and diluted to the appropriate final Ester butyl Penoxsulam IPOHE concentrations with the addition of 9 mL of an aqueous mix gae/ha. gai?ha gai?ha Obs Exp ture of 1.25% (v/v) crop oil concentrate so that the final spray 8 O O 15 solutions contained 1.25% (v/v) crop oil concentrate. 16 O O 33 0221 For treatments comprised of formulated and techni O 35 O O cal compounds, weighed amounts of the technical materials O O 8.75 48 were placed individually in 25 mL glass vials and dissolved in 8 35 8.75 62 56 a volume of 97:3 V/v acetone/DMSO to obtain 12x Stock 16 35 8.75 90 66 Solutions, and measured amounts of the formulated com pounds were placed individually in 25 mL glass vials and diluted in a volume of 1.5% (v/v) crop oil concentrate to obtain 12x Stock solutions. If a test compound does not dis TABLE 50 Solve readily, the mixture was warmed and/or Sonicated. Synergistic Activity of Foliar-Applied Compound A Benzyl Application Solutions were prepared by adding an appropri Ester, Cyhalofop-Butyl, and Bentazon Ternary Herbicidal ate amount of each Stock Solution (e.g., 1 mL) and diluted to Compositions on Weed Control in a Rice Cropping System. the appropriate final concentrations with the addition of an Visual Weed appropriate amount of an aqueous mixture of 1.5% (v/v) crop Compound Control (%)- oil concentrate so that the final spray solutions contained A Benzyl Cyhalofop- Bentazon 21 DAA 1.25% (v/v) crop oil concentrate. As required, additional Ester butyl sodium IPOHE water and/or 97.3 V/vacetone/DMSO was added to individual application solutions so that the final acetone and DMSO gae/ha. gai?ha gae/ha. Obs Exp concentrations of the application Solutions being compared 2.19 O O 30 were 8.1% and 0.25%, respectively. 4.38 O O 38 0222 All stock solutions and applications solutions were O 35 O O visually inspected for compound compatibility prior to appli O O 420 53 2.19 35 420 70 67 cation. Spray solutions were applied to the plant material with 4.38 35 420 82 71 an overhead Mandel track sprayer equipped with a 8002E 8 O O 15 nozzles calibrated to deliver 187L/ha over an application area 16 O O 33 of 0.503 m at a spray height of 18 inches (46 cm) above O 35 O O average plant canopy height. Control plants were sprayed in O O 420 75 the same manner with the solvent blank. 8 35 420 85 79 0223) The treated plants and control plants were placed in 16 35 420 93 83 a greenhouse as described above and watered by Sub-irriga tion to prevent wash-off of the test compounds. After approxi mately 3 weeks, the condition of the test plants as compared TABLE 51 with that of the untreated plants was determined visually and Synergistic Activity of Foliar-Applied Compound A Benzyl Ester, scored on a scale of 0 to 100 percent where 0 corresponds to Cyhalofop-Butyl, and Triclopyr TEA Salt Ternary Herbicidal no injury or growth inhibition and 100 corresponds to com Compositions on Weed Control in a Rice Cropping System. plete kill. Com 0224 Colby's equation was used to determine the herbi pound Cy- Tri cidal effects expected from the mixtures (Colby, S.R. 1967. A. hal- clopyr Visual Weed Control Calculation of the synergistic and antagonistic response of Benzyl ofop- TEA (%) - 21 DAA herbicide combinations. Weeds 15:20-22.). 0225. The following equation was used to calculate the Ester butyl Salt ECHCG ECHCO SCPU expected activity of mixtures containing three active ingredi gae/ha. gai?ha gae?ha Obs Exp Obs Exp Obs Exp ents, A, B, and C: 2.19 O O 5 10 65 Expected=A+B+C-((AxB+AxC+BxC)/100)+(AxBxC/ 4.38 O O 27 25 96 10000) O 35 O 2O 37 O O O 17.5 O 3 43 0226 A observed efficacy of active ingredient A at the 2.19 35 17.5 35 24 45 45 98 8O same concentration as used in the mixture. 4.38 35 17.5 37 41 90 S4 100 98 0227 B-observed efficacy of active ingredient B at the same concentration as used in the mixture. US 2014/003 1228A1 Jan. 30, 2014 42

TABLE 51-continued TABLE 54

Synergistic Activity of Foliar-Applied Compound A Benzyl Ester, Synergistic Activity of Foliar-Applied Compound A Benzyl Ester, Cyhalofop-Butyl, and Benzobicyclon Ternary Herbicidal Compositions Cyhalofop-Butyl, and Triclopyr TEA Salt Ternary Herbicidal on Weed Control in a Rice Cropping System. Compositions on Weed Control in a Rice Cropping System. Visual Weed Com Compound Control (%)- pound Cyhal Tri Visual Weed Control A Benzyl Cyhalofop- 21 DAA A Benzyl ofop clopyr (%) - 21 DAA Ester butyl Benzobicyclon ECHCG Ester butyl TEA Salt CYPIR gae/ha. gai?ha gai?ha Obs Exp gae/ha. gai?ha gae/ha. Obs Exp 8 O O 38 O 35 O 2O 8 53 O O 200 O 16 95 8 35 200 90 50 O 35 O O O 17.5 O Visual Weed 8 35 17.5 100 53 Compound Control (%)- A Benzyl Cyhalofop- 21 DAA 16 35 17.5 100 95 Ester butyl Benzobicyclon IPOHE

gae/ha. gai?ha gai?ha Obs Exp

TABLE 52 8 O O 10 Synergistic Activity of Foliar-Applied Compound A Benzyl Ester, 16 O O 30 Cyhalofop-Butyl, and Bispyribac Sodium Ternary Herbicidal O 35 O O Compositions on Weed Control in a Rice Cropping System. O O 200 55 8 35 200 78 60 Compound Cyhal- Bispyr- Visual Weed Control 16 35 2OO 85 69 A Benzyl ofop- ibac %) - 21 DAA

Ester butyl sodium IPOHE CYPES gae/ha. gai?ha gai?ha Obs Exp Obs Exp TABLE 55 O O 10 70 Synergistic Activity of Foliar-Applied Compound A Benzyl 35 O O O Ester, Cyhalofop-Butyl, and Quinclorac Ternary Herbicidal O 28 60 2O Compositions on Weed Control in a Rice Cropping System. 35 28 83 64 90 76 Compound Cyhal- Visual Weed Control A Benzyl ofop- Quin- %) - 21 DAA TABLE 53 Ester butyl clorac ECHCG CYPES Synergistic Activity of Foliar-Applied Compound A Benzyl Ester, gae/ha. gai?ha gai?ha Obs Exp Obs Exp Cyhalofop-Butyl, and Imazamox Ammonium Ternary Herbicidal Compositions on Weed Control in a Rice Cropping System. 8 O O 38 70 O 35 O 2O O Visual Weed O O 28O 10 O Compound Control (%)- 8 35 28O 92 55 85 70 A Benzyl Cyhalofop Imazamox 21 DAA Ester butyl ammonium CYPES gae/ha. Obs Exp TABLE 56 O O 70 Synergistic Activity of Foliar-Applied Compound A 35 O O Benzyl Ester, Cyhalofop-Butyl, and Glyphosate Dimethylammonium O 12 60 (DMA) Salt Ternary Herbicidal Compositions on Weed 35 12 95 88 Control in a Rice Cropping System. Visual Weed Visual Weed Compound Control (%)- Compound Control (%)- A Benzyl Cyhalofop Imazamox 21 DAA A Benzyl Cyhalofop- Glyphosate 21 DAA Ester butyl ammonium IPOHE Ester butyl DMA LEFCEH gae/ha. gae/ha. Obs Exp gae/ha. gai?ha gai?ha Obs Exp

O 2O 16 O O 25 17.5 O O 35 O 68 O 65 O O 420 45 17.5 85 72 16 35 420 93 87 US 2014/003 1228A1 Jan. 30, 2014

TABLE 56-continued TABLE 59 Synergistic Activity of Foliar-Applied Compound A Benzyl Ester, Synergistic Activity of Foliar-Applied Compound A Cyhalofop-Butyl, and Propyrisulfuron Ternary Herbicidal Compositions Benzyl Ester, Cyhalofop-Butyl, and Glyphosate Dimethylammonium on Weed Control in a Rice Cropping System. (DMA) Salt Ternary Herbicidal Compositions on Weed Visual Weed Control in a Rice Cropping System. Compound Control (%)- A Benzyl Cyhalofop- 22 DAA Ester butyl Propyrisulfuron ECHOR Visual Weed Compound Control (%)- gae/ha. gai?ha gai?ha Obs Exp A Benzyl Cyhalofop- Glyphosate 21 DAA 8 O O 13 Ester butyl DMA ECHCG O 35 O 15 O O 22.5 55 gae/ha. gai?ha gae/ha. Obs Exp 8 35 22.5 78 67

8 O O 45 O 17.5 O 33 TABLE 60 O O 105 23 Synergistic Activity of Foliar-Applied Compound A Benzyl Ester, Fenoxaprop-p-Ethyl + Isoxadifen 8 17.5 105 83 71 ethyl, and PenoxSulam Ternary Herbicidal Compositions on Weed Control in a Rice Cropping System. Fenoxaprop- Visual Weed Compound p-ethyl + Control (%)- TABLE 57 A Benzyl Isoxadifen- 22 DAA Synergistic Activity of Foliar-Applied Compound A Benzyl Ester, Ester PenoxSulam ethyl ECHOR Cyhalofop-Butyl, and Glufosinate Ammonium Ternary Herbicidal Compositions on Weed Control in a Rice Cropping System. gae/ha. gai?ha gai?ha Obs Exp 8 O O 25 Visual Weed 16 O O 35 Compound Control (%)- O 4.38 O 45 A Benzyl Cyhalofop- Glufosinate 21 DAA O 8.75 O 53 Ester butyl ammonium ECHCO O O 4.38 O 8 4.38 4.38 73 59 gae/ha. gai?ha gai?ha Obs Exp 8 8.75 4.38 62 65 16 4.38 4.38 82 64 8 O O 45 16 8.75 4.38 87 70 O 35 O 40 O O 115 O Fenoxaprop- Visual Weed 8 35 115 8O 67 Compound p-ethyl + Control (%)- A Benzyl Isoxadifen- 22 DAA Ester PenoxSulam ethyl CYPIR

TABLE 58 gae/ha. gai?ha gai?ha Obs Exp Synergistic Activity of Foliar-Applied Compound A Benzyl 8 O O 37 Ester, Cyhalofop-Butyl, and FentraZamide Ternary Herbicidal O 4.38 O 50 O O 4.38 O Compositions on Weed Control in a Rice Cropping System. O O 8.75 O Compound Cyhal- Fen- Visual Weed Control 8 4.38 4.38 83 68 A Benzyl ofop- traZa- %) - 22 DAA 8 4.38 8.75 88 68

Ester butyl mide ECHCG ECHOR gae/ha. gai?ha gai?ha Obs Exp Obs Exp TABLE 61 8 O O 40 13 Synergistic Activity of Foliar-Applied Compound A Benzyl 16 O O 58 40 Ester, Profoxydim, and PenoxSulam Ternary Herbicidal Compositions O 17.5 O O O on Weed Control in a Rice Cropping System. O 35 O 12 15 O O 33.75 O 3 Visual Weed O O 67.5 O O Compound Control (%)- 8 17.5 33.75 40 40 25 16 A Benzyl 22 DAA 8 17.5 67.5 67 40 52 13 Ester PenoxSulam Profoxydim ECHOR 8 35 33.75 48 47 63 29 8 35 67.5 65 47 55 26 gae/ha. gai?ha gai?ha Obs Exp 16 17.5 33.75 83 58 60 42 16 17.5 67.5 8O 58 82 40 8 O O 25 16 35 33.75 92 63 8O 51 16 O O 35 16 35 67.5 87 63 87 49 O 4.38 O 45 O O 3.12 O US 2014/003 1228A1 Jan. 30, 2014 44

TABLE 61-continued Rice seeds were planted in Sun Gro MetroMix R. 306 planting mixture, which typically has a pH of 6.0 to 6.8 and an organic Synergistic Activity of Foliar-Applied Compound A Benzyl matter content of about 30 percent, in plastic plug trays. Ester, Profoxydim, and PenoxSulam Ternary Herbicidal Compositions Seedlings at the second or third leaf stage of growth were on Weed Control in a Rice Cropping System. transplanted into 860 mL of mud contained in 32-oZ. non 8 4.38 3.12 73 59 perforated plastic pots with a surface area of 86.59 cm 4 days 16 4.38 3.12 70 64 prior to herbicide application. The paddy was created by Visual Weed filling the headspace of the pots with 2.5 to 3 cm of water. Compound Control (%)- When required to ensure good germination and healthy A Benzyl 22 DAA plants, a fungicide treatment and/or other chemical or physi Ester PenoxSulam Profoxydim CYPIR cal treatment was applied. The plants were grown for 4-22 gae/ha. gai?ha gai?ha Obs Exp days in a greenhouse with an approximate 14 hr photoperiod which was maintained at about 29C during the day and 26°C. 8 O O 37 during the night. Nutrients were added as Osmocote(R) (19:6: O 4.38 O 50 O O 3.12 O 12, N:P:K+minor nutrients) at 2 g per 16-oZ. pot and 4g per O O 6.25 O 32-oZ. pot. Water was added on a regular basis to maintain the 8 4.38 3.12 87 68 paddy flood, and Supplemental lighting was provided with 8 4.38 6.25 87 68 overhead metal halide 1000-Watt lamps as necessary. The plants were employed for testing when they reached the first through fourth true leaf stage. TABLE 62 0231. Treatments consisted of the benzyl ester of Synergistic Activity of Foliar-Applied Compound A Benzyl 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-meth Ester, Cyhalofop-butyl, and Indianofan Ternary Herbicidal oxy-phenyl)pyridine-2-carboxylic acid (Compound A), for Compositions on Weed Control in a Rice Cropping System. mulated as an SC (Suspension concentrate), an ACCase inhibitor herbicide, and a third herbicidal component, each Visual Weed Compound Control (%)- applied alone and in ternary combination. Forms of com A Benzyl Cyhalofop- 22 DAA pound A were applied on an acid equivalent basis. Ester butyl Indanofan LEFCEH Forms of compound A (compound of formula I) tested gae/ha. gai?ha gai?ha Obs Exp include:

8 O O 28 O 35 O 70 Compound A O O 72.5 30 O O 145 38 8 35 72.5 95 85 8 35 145 98 86 CYPES Cyperus esculentus L. nutsedge, yellow CYPIR Cyperus iria L. flatsedge, rice ECHCG Echinochloa crusgalli (L.) Beauv. barnyardgrass ECHCO Echinochloa colona (L.) Link junglerice ECHOR Echinochloa oryzoides (Ard.) Fritsch early watergrass IPOHE Ipomoea hederacea Jacq. morning glory, ivyleaf LEFCH Leptochloa chinensis (L.) Nees sprangletop, Chinese SCPJU Schoenopiectus iuncoides (Roxb.) Palla bulrush, Japanese gae/ha = grams acid equivalent per hectare gai?ha = grams active ingredient per hectare Benzyl Ester Obs = observed value Exp = expected value as calculated by Colby's equation DAA = days after application 0232. The ACCase inhibitor component was applied on an active ingredient basis and included cyhalofop-R-butyl for Example VI mulated as Clincher R G and metamifop formulated as Metamifop EC. Other herbicidal components were applied on an active ingredient or acid equivalent basis depending on Evaluation of In-Water Applied Ternary Herbicidal the compound and included penoXSulam formulated as Mixtures for Weed Control in Transplanted Paddy GraspR SC, bentazon sodium formulated as BasagranR), tri Rice clopyr trimethylammonium (TEA) salt formulated as Grand 0230 Weed seeds or nutlets of the desired test plant spe stand(R) R, benzobicyclon formulated as Benzobicyclon, ben cies were planted in puddled soil (mud) prepared by mixing a furesate formulated as Full Slot(R) WG, pyraclonil formulated shredded, non-sterilized mineral soil (50.5 percent silt, 25.5 as Pyraclonr) Flowable, mefenacet (technical grade mate percent clay, and 24 percent sand, with a pH of about 7.6 and rial), and pretilachlor (technical grade material). an organic matter content of about 2.9 percent) and water at a 0233 Treatment requirements for each compound or her 1:1 volumetric ratio. The prepared mud was dispensed in 365 bicidal component were calculated based upon the rates being mL aliquots into 16-ounce (oZ.) non-perforated plastic pots tested, the concentration of active ingredient or acid equiva with a surface area of 86.59 square centimeters (cm) leaving lent in the formulation, an application Volume of 1 mL per a headspace of 3 centimeters (cm) in each pot. Mud was component perpot, and an application area of 86.59 cm per allowed to dry overnight prior to planting or transplanting. pot. US 2014/003 1228A1 Jan. 30, 2014 45

0234 For formulated compounds, a measured amount TABLE 63-continued was placed in an individual 100 or 200 mL. glass vial and was dissolved in a volume of 1.25% (v/v) Agri-Dex(R) crop oil Synergistic Activity of In-Water Applications of Compound A Benzyl Ester, Cyhalofop-butyl, and PenoxSulam Ternary Herbicidal concentrate to obtain application Solutions. If the test com- Compositions on Weed Control in a Rice Cropping System. pound did not dissolve readily, the mixture was warmed and/ or Sonicated. 1.09 45 1.25 65 39 45 19 0235 For technical grade compounds, a weighed amount 2.19 45 1.25 87 56 87 25 was placed in an individual 100 to 200 mL. glass vial and was Compound Cyhal dissolved in a Volume of acetone to obtain concentrated Stock A Benzyl ofop- Penox- Visual Weed Control (%) - 21 DAA solutions. If the test compound did not dissolve readily, the Ester butyl Sulam ECHCG mixture was warmed and/or Sonicated. The concentrated gae/ha. gai?ha gai?ha Obs Exp stock solutions obtained were diluted with an equivalent vol ume of an aqueous mixture containing 2.5% (v/v) oil concen- 4 O O 25 trate so that the final application solutions contained 1.25% 8 O O 45 (V/v) crop oil concentrate. 1. 4. g 0236. Applications were made by injecting with a pipetter O O 2.5 55 appropriate amounts of the application Solutions, into the 4 45 2.5 85 76 aqueous layer of the paddy. Control plants were treated in the 8 45 2.5 100 83 same manner with the solvent blank. Applications were made 16 45 2.5 100 1OO so that all treated plant material received the same concentra- Compound Cyhal tions of acetone and crop oil concentrate. A Benzyl ofop- Penox- Visual Weed Control (%) - 21 DAA 0237. The treated plants and control plants were placed in Ester butyl Sulam CYPRO a greenhouse as described above and water was added as gae/ha. gai?ha gai?ha Obs Exp needed to maintain a paddy flood. After approximately 3 weeks the condition of the test plants as compared with that of 2.19 O O O the untreated plants was determined visually and scored on a g g g scale of 0 to 100 percent where 0 corresponds to no injury or O O 1.25 O growth inhibition and 100 corresponds to complete kill. 2.19 22.5 1.25 23 O 0238 Colby's equation was used to determine the herbi- 2.19 45 1.25 28 O cidal effects expected from the mixtures (Colby, S.R. 1967. Compoundpoun Cwhalyna Calculation of the synergistic and antagonistic response of A Benzyl ofop- Penox- Visual Weed Control (%) - 24 DAA herbicide combinations. Weeds 15:20-22.). Ester butyl Sulam CYPRO 0239) The following equation was used to calculate the gae/ha. gai?ha gai?ha Obs Exp expected activity of mixtures containing three active ingredi ents, A, B, and C: 4 O O 40 8 O O 60 Expected=A+B+C-((AxB+AxC+BxC)/100)+(AxBxC/ 16 O O 85 10000) O 90 O O 0240 A observed efficacy of active ingredient A at the g 1s 5 g same concentration as used in the mixture. O O 5 O 0241 B-observed efficacy of active ingredient B at the 4 90 2.5 60 40 same concentration as used in the mixture. . g 3. 3. 0242 C-observed efficacy of active ingredient C at the 4 90 s 68 40 same concentration as used in the mixture. 8 90 5 90 60 0243 The compounds tested, application rates employed, g r 5 plant species tested, and results are given in Tables 63-71. 8 18O 2.5 90 60 16 18O 2.5 100 85 TABLE 63 4 18O 5 50 40 8 18O 5 95 60 Synergistic Activity of In-Water Applications of Compound A 16 18O 5 100 85 Benzyl Ester, Cyhalofop-butyl, and PenoxSulam Ternary Herbicidal Compositions on Weed Control in a Rice Cropping System. Compound Cyhal A Benzyl ofop- Penox- Visual Weed Control (%) - 24 DAA Compound Cyhal- Ester butyl Sulam FIMMI A Benzyl ofop- Penox- Visual Weed Control (%) - 21 DAA gae/ha. gai?ha gai?ha Obs Exp Ester butyl Sulam FIMMI ECHCG 4 O O O gae/ha. gai?ha gai?ha Obs Exp Obs Exp 8 O O 50 16 O O 30 1.09 O O 8 O O 90 O O 2.19 O O 33 7 O 18O O 2O O 22.5 O 33 O O O 2.5 60 O 45 O O 3 4 90 2.5 78 60 O O 1.25 33 17 8 90 2.5 95 8O 1.09 22.5 1.25 70 59 28 17 16 90 2.5 100 72 2.19 22.5 1.25 95 70 58 22 4 18O 2.5 90 68 US 2014/003 1228A1 Jan. 30, 2014 46

TABLE 63-continued TABLE 65 Synergistic Activity of In-Water Applications of Compound A Synergistic Activity of In-Water Applications of Compound Benzyl Ester, Cyhalofop-butyl, and PenoxSulam Ternary Herbicidal A Benzyl Ester, Cyhalofop-butyl, and Triclopyr Trimethylammonium Compositions on Weed Control in a Rice Cropping System. (TEA) Salt Ternary Herbicidal Compositions on Weed Control in a Rice Cropping System. 8 18O 2.5 8O 84 Visual Weed 16 18O 2.5 99 78 Compound Control (%)- A Benzyl Cyhalofop- Triclopyr 21 DAA Compound Cyhal Ester butyl TEA ECHCG A Benzyl ofop- Penox- Visual Weed Control (%) - 24 DAA Ester butyl Sulam SCPMA gae/ha. gai?ha gae/ha. Obs Exp

gae/ha. gai?ha gai?ha Obs Exp 1.09 O O O 2.19 O O 7 4 O O O O 22.5 O O 8 O O O O 45 O 3 16 O O O O O 17.5 O O 18O O O 1.09 22.5 17.5 25 O O O 5 30 2.19 22.5 17.5 48 7 1.09 45 17.5 37 3 4 18O 5 25 30 2.19 45 17.5 48 10 8 18O 5 70 30 16 18O 5 8O 30 Visual Weed Compound Control (%)- A Benzyl Cyhalofop- Triclopyr 21 DAA Ester butyl TEA ECHCG TABLE 64 gae/ha. gai?ha gai?ha Obs Exp Synergistic Activity of In-Water Applications of Compound A Benzyl Ester, Cyhalofop-butyl, and Bentazon Sodium Ternary Herbicidal 4 O O 25 Compositions on Weed Control in a Rice Cropping System. 8 O O 45 16 O O 99 Visual Weed O 45 O 30 Compound Control (%)- O O 35 O A Benzyl Cyhalofop- Bentazon 21 DAA 4 45 35 1OO 48 Ester butyl Sodium ECHCG 8 45 35 1OO 62 16 45 35 95 99 gae/ha. gai?ha gae/ha. Obs Exp Visual Weed 1.09 O O O Compound Control (%)- 2.19 O O 7 A Benzyl Cyhalofop- Triclopyr 21 DAA O 22.5 O O Ester butyl TEA SCPU O 45 O 3 O O 210 O gae/ha. gai?ha gae/ha. Obs Exp 1.09 22.5 210 2O O 2.19 22.5 210 17 7 2.19 O O 77 1.09 45 210 13 3 O 22.5 O O 2.19 45 210 72 10 O 45 O O 4 O O 25 8 O O 45 O O 17.5 8 16 O O 99 2.19 22.5 17.5 93 79 O 45 O 30 2.19 45 17.5 88 79 O O 420 15 4 45 420 85 55 8 45 420 1OO 67 16 45 420 1OO 99 TABLE 66 Visual Weed Synergistic Activity of In-Water Applications of Compound A Compound Control (%)- Benzyl Ester, Cyhalofop-butyl, and Benfuresate Ternary Herbicidal A Benzyl Cyhalofop- Bentazon 21 DAA Compositions on Weed Control in a Rice Cropping System. Ester butyl Sodium FIMMI Visual Weed gae/ha. gai?ha gae/ha. Obs Exp Compound Control (%) - 21 A Benzyl Cyhalofop- DAA 1.09 O O 8 Ester butyl Benfuresate ECHCG 2.19 O O 33 O 45 O O gae/ha. gai?ha gai?ha Obs Exp O O 210 17 1.09 45 210 33 24 4 O O 25 2.19 45 210 68 44 8 O O 45 4 O O 62 16 O O 99 O 22.5 O O O 45 O 30 O 45 O O O O 150 O O O 420 30 4 45 150 95 48 4 22.5 420 93 73 8 45 150 95 62 4 45 420 1OO 73 16 45 150 100 99 US 2014/003 1228A1 Jan. 30, 2014 47

TABLE 67 TABLE 68-continued Synergistic Activity of In-Water Applications of Compound A Benzyl Synergistic Activity of In-Water Applications of Compound A Ester, Cyhalofop-butyl, and Benzobicyclon Ternary Herbicidal Benzyl Ester, Cyhalofop-butyl, and Pyraclonil Ternary Herbicidal Compositions on Weed Control in a Rice Cropping System. Compositions on Weed Control in a Rice Cropping System. Visual Weed Visual Weed Compound Control (%)- A Benzyl Cyhalofop- 21 DAA Compound Control (%)- Ester butyl Benzobicyclon ECHCG A Benzyl Cyhalofop- 21 DAA Ester butyl Pyraclonil SCPMA gae/ha. gai?ha gai?ha Obs Exp gae/ha. gai?ha gai?ha Obs Exp 4 O O 25 O 45 O 30 4 O O O O O 100 2O 8 O O O 4 45 100 100 58 16 O O O O 22.5 O O Visual Weed O 45 O O Compound Control (%)- O O 22.5 78 A Benzyl Cyhalofop- 24 DAA 4 22.5 22.5 83 78 Ester butyl Benzobicyclon ECHOR 8 22.5 22.5 1OO 78 16 22.5 22.5 93 78 gae/ha. gai?ha gai?ha Obs Exp 4 45 22.5 95 78 8 45 22.5 98 78 4 O O O 16 45 22.5 90 78 8 O O O 16 O O 10 O 90 O 25 O O 25 10 O O 50 10 TABLE 69 4 90 25 35 33 8 90 25 40 33 Synergistic Activity of In-Water Applications of Compound A 16 90 25 100 39 Benzyl Ester, Cyhalofop-butyl, and Mefenacet Ternary Herbicidal 4 90 50 2O 33 Compositions on Weed Control in a Rice Cropping System. 8 90 50 100 33 16 90 50 85 39 Visual Weed Compound Control (%)- Visual Weed A Benzyl Cyhalofop- 21 DAA Compound Control (%)- Ester butyl Mefenacet CYPRO A Benzyl Cyhalofop- 24 DAA Ester butyl Benzobicyclon FIMMI gae/ha. gai?ha gai?ha Obs Exp gae/ha. gai?ha gai?ha Obs Exp 4 O O 3 8 O O 33 O 90 O O 4 O O O O 18O O O 8 O O 50 O O 75 O 16 O O 30 O O 150 O O 18O O 2O 4 90 75 15 3 O O 50 68 8 90 75 55 33 4 18O 50 88 74 4 90 150 75 3 8 18O 50 100 87 8 90 150 50 33 16 18O 50 100 82 4 18O 75 68 3 8 18O 75 60 33 4 18O 150 35 3 8 18O 150 63 33 TABLE 68 Synergistic Activity of In-Water Applications of Compound A Benzyl Ester, Cyhalofop-butyl, and Pyraclonil Ternary Herbicidal TABLE 70 Compositions on Weed Control in a Rice Cropping System. Synergistic Activity of In-Water Applications of Compound Visual Weed A Benzyl Ester, Cyhalofop-butyl, and Pretilachlor. Compound Control (%)- A Benzyl Cyhalofop- 21 DAA Visual Weed Ester butyl Pyraclonil ECHCG Compound Control (%)- A Benzyl Cyhalofop- 21 DAA gae/ha. gai?ha gai?ha Obs Exp Ester butyl Pretilachlor CYPRO 4 O O 25 gae/ha. gai?ha gai?ha Obs Exp 8 O O 45 16 O O 99 4 O O 3 O 45 O 30 8 O O 33 O O 22.5 30 O 18O O O 4 45 22.5 1OO 63 O O 25 O 8 45 22.5 1OO 73 O O 50 O 16 45 22.5 1OO 100 4 18O 25 30 3 8 18O 25 1OO 33 US 2014/003 1228A1 Jan. 30, 2014 48

TABLE 70-continued 2. The composition of claim 1, wherein (a) is a Calkyl or benzyl ester of compound (I). Synergistic Activity of In-Water Applications of Compound 3. The composition of claim 2, wherein (a) is a benzyl ester A BenZVI Ester, Cyhalofop-butyl, and Pretilachlor. of compound (I). Visual Weed 4. The composition of claim 1, wherein (a) is the compound Compound Control (%)- of formula (I), which is the carboxylic acid. A Benzyl Cyhalofop- 21 DAA 5. The composition of claim 1, wherein (b) is clethodim, Ester butyl Pretilachlor CYPRO clodinafop-propargyl, cyhalofop-R-butyl, diclofop-methyl, gae/ha. gai?ha gai?ha Obs Exp fenoxaprop-P-ethyl, fluazifop-P-butyl, haloxyfop-R-methyl, metamifop, pinoxaden, profoxydim, quizalofop-P-ethyl, set 4 18O 50 35 3 8 18O 50 55 33 hoxydim or tralkoxydim. 6. The composition according to claim 5, wherein the ratio of compound (a) to compound (b) is such that the composition exhibits herbicidal synergy. TABLE 71 6. The composition of claim 1, wherein (b) is cyhalofop Synergistic Activity of In-Water Applications of Compound butyl or carboxylic acid, carboxylate salt, or ester thereof, A Benzyl Ester, Metamifop, and PenoxSulam Ternary Herbicidal wherein the composition further comprises penoXSulam, ben Compositions on Weed Control in a Rice Cropping System. taZon-sodium, triclopyr, bispyribac-Sodium, imaZamox, ben Visual Weed Zobicyclon, quinclorac, glyphosate, glufosinate, benfuresate, Compound Control (%)- fentraZamide, indanofan, ipfencarbazone, mefenacet, A Benzyl 24 DAA oxazichlomefone, pretilachlor, propyrisulfuron, pyraclonil. Ester PenoxSulam Metamifop ECHOR pyriftalid, or pyrimisulfan, or an agriculturally acceptable salt, carboxylic acid, carboxylate salt, or ester thereof, in gae/ha. gai?ha gai?ha Obs Exp combination as a synergistic 3 way/ternary mixture. 8 O O 10 8. The composition of claim 1, wherein (b) is fenoxaprop, 16 O O 25 O 5 O 65 metamifop, or profoxydim, or agriculturally acceptable salt, O 10 O 93 ester, carboxylate salt, or carboxylic acid thereof, wherein the O O 25 10 composition further comprises penoXSulam, or an agricultur O O 50 18 ally acceptable salt, carboxylic acid, carboxylate salt, or ester 8 5 25 83 72 16 10 25 83 95 thereof, in combination as a synergistic 3 way/ternary mix 8 5 50 1OO 74 ture. 16 10 50 1OO 95 9. A method of controlling undesirable vegetation which comprises contacting the vegetation or the locus thereof with CYPRO Cyperus rotundus L. nutsedge, purple ECHCG Echinochloa crusgalli (L.) Beauv. barnyardgrass or applying to the Soil or water to prevent the emergence or ECHOR Echinochloa oryzoides (Ard.) Fritsch watergrass, early growth of vegetation the composition of claim 1. FIMMI Fimbristylis miliacea (L.) Vahl fringerush, globe 10. A method of controlling undesirable vegetation which SCPJU Schoenopiectus iuncoides (Roxb.) Palla bulrush, Japanese comprises contacting the vegetation or the locus thereof with SCPMA Bolboschoenus maritimus (L.) Palla or clubrush, sea Schoenopiectus maritimus (L.) Lye or applying to the Soil or water to prevent the emergence or gae/ha = grams acid equivalent per hectare growth of vegetation utilizing a herbicidally effective amount gai?ha = grams active ingredient per hectare of (a) a compound of the formula (I) Obs = observed value Exp = expected value as calculated by Colby's equation DAA = days after application

(I) What is claimed is: 1. A herbicidal composition, comprising: a herbicidally effective amount of (a) a compound of the formula (I)

(I)

or an agriculturally acceptable salt or ester of thereof, and (b) an ACCase inhibitor. 11. The method of claim 10, wherein the undesirable veg etation is controlled in rice, cereals, wheat, barley, oats, rye, Sorghum, corn/maize, Sugarcane, Sunflower, oilseed rape, canola, Sugar beet, soybean, cotton, pineapple, pastures, grasslands, rangelands, fallowland, turf, tree and vine or an agriculturally acceptable salt or ester thereof: and orchards, aquatics, plantation crops, vegetables, industrial (b) ACCase inhibitors, or a salt or ester thereof. vegetation management (IVM) or rights of way (ROW). US 2014/003 1228A1 Jan. 30, 2014 49

12. The method of claim 10, wherein the undesirable veg 17. The method of claim 16, wherein the tolerant crop etation is immature. possesses multiple or stacked traits conferring tolerance to 13. The method of claim 10, wherein the (a) and (b) are multiple herbicides or multiple modes of action. applied to water. 18. The method of claim 10, wherein the undesirable veg 14. The method of claim 13, wherein the water is part of a etation comprises a herbicide resistant or tolerant weed. flooded rice paddy. 19. The method of claim 18, wherein the resistant or toler 15. The method of claim 10, wherein the (a) and (b) are ant weed is a biotype with resistance or tolerance to multiple applied post-emergently and/or post emergently to the weed herbicides, multiple chemical classes, or multiple herbicide or crop. 16. The method of claim 10, wherein the undesirable veg modes-of-action or via multiple resistance mechanisms. etation is controlled in glyphosate-, 5-enolpyruvylshikimate 20. The method of claim 18, wherein the resistant or toler 3-phosphate (EPSP) synthase inhibitor-, glufosinate ant weed is a biotype resistant or tolerant to acetolactate glutamine synthetase inhibitor-, dicamba-, phenoxy auxin-, synthase (ALS) or acetohydroxy acid synthase (AHAS) pyridyloxy auxin-, synthetic auxin-, auxin transport inhibi inhibitors, photosystem II inhibitors, acetyl CoA carboxylase tor-, aryloxyphenoxypropionate-, cyclohexanedione-, phe (ACCase) inhibitors, synthetic auxins, auxin transport inhibi nylpyrazoline-, acetyl CoA carboxylase (ACCase) inhibitor tors, photosystem I inhibitors, 5-enolpyruvylshikimate-3- imidazolinone-, Sulfonylurea-, pyrimidinylthiobenzoate-, phosphate (EPSP) synthase inhibitors, microtubule assembly triazolopyrimidine-, Sulfonylaminocarbonyltriazolinone-, inhibitors, fatty acid and lipid synthesis inhibitors, protopor acetolactate synthase (ALS) or acetohydroxy acid synthase phyrinogen oxidase (PPO) inhibitors, carotenoid biosynthe (AHAS) inhibitor-, 4-hydroxyphenyl-pyruvate dioxygenase sis inhibitors, very long chain fatty acid (VLCFA) inhibitors, (HPPD) inhibitor-, phytoene desaturase inhibitor-, caro phytoene desaturase (PDS) inhibitors, glutamine synthetase tenoid biosynthesis inhibitor-, protoporphyrinogen oxidase inhibitors, 4-hydroxyphenyl-pyruvate-dioxygenase (HPPD) (PPO) inhibitor-, cellulose biosynthesis inhibitor-, mitosis inhibitors, mitosis inhibitors, cellulose biosynthesis inhibi inhibitor-, microtubule inhibitor-, very long chain fatty acid tors, herbicides with multiple modes-of-action, quinclorac, inhibitor-, fatty acid and lipid biosynthesis inhibitor-, photo arylaminopropionic acids, difenZoquat, endothall, or orga system I inhibitor-, photosystem II inhibitor-, triazine-, or noarsenicals. bromoxynil-tolerant crops.