sign in sign up
<<
Home , Butafenacil, Sulfentrazone

US 20140087947A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2014/0087947 A1 Michel (43) Pub. Date: Mar. 27, 2014

(54) HERBICIDAL COMPOSITIONS (52) U.S. Cl. CPC ...... A0IN 25/32 (2013.01); A0IN 41/06 (75) Inventor: Albrecht Michel, Basel (CH) (2013.01); A0IN 43/84 (2013.01); A0IN 43/653 (2013.01); A0IN 37/48 (2013.01); A0IN33/22 (2013.01) (73) Assignee: SYNGENTA PARTICIPATIONS AG, USPC ...... SO4/112 Basel (CH) (57) ABSTRACT The present invention provides, interalia, a herbicidal com (21) Appl. No.: 14/119,515 position comprising: (i) a protoporphyrinogen oxidase inhib iting selected from the group consisting flumiox (22) PCT Filed: May 31, 2012 azin, , and a diphenyl ether selected from the group consisting of (including acifluro (86). PCT No.: PCT/EP2012/06O234 fen-Sodium), (including fomesafen-Sodium), S371 (c)(1) and oxyfluorfen: oran agronomically acceptable salt (2), (4) Date: Nov. 22, 2013 of said herbicide; and (ii) a safener of Formula (II) or an agronomically acceptable salt of said compound, wherein:— is selected from the group consisting of halogen, nitro, C-C, (30) Foreign Application Priority Data alkyl, C-Chaloalkyl, C-Chaloalkoxy, C-C cycloalkyl, phenyl, C-C alkoxy, cyano, C-C alkylthio, C-C alkyl Jun. 1, 2011 (EP) ...... 11092392 sulfinyl, C-C alkylsulfonyl, C-C alkoxycarbonyl and C-C alkylcarbonyl; and R and R are independently selected from the group consisting of hydrogen, C-C alkyl, Publication Classification C-C cycloalkyl, C-C alkenyl and C-C alkynyl. (II) (51) Int. Cl. O O AOIN 25/32 (2006.01) | Ji AOIN33/22 (2006.01) N-S N AOIN 43/653 (2006.01) ka i? ( N-R AOIN 37/48 (2006.01) O AOIN 4I/06 (2006.01) O RC AOIN 43/84 (2006.01) US 2014/0O87947 A1 Mar. 27, 2014

HERBICIDAL COMPOSITIONS luoroethoxy O 2.2.2-trichloroethoxy, preferably difluoromethoxy, 2-chloroethoxy or trifluoromethoxy. 0001. The present invention relates to improved herbicid 0012 Alkylthio is, for example, methylthio, ethylthio. ally active compositions comprising certain protoporphy propylthio, isopropylthio, n-butylthio, isobutylthio. Sec-bu rinogen oxidase (PPGO) inhibiting and certain tylthio or tert-butylthio, preferably methylthio or ethylthio. defined herbicide safeners. The present invention further Alkylsulfinyl is, for example, methylsulfinyl, ethylsulfinyl, relates to the use of the improved herbicidal compositions for propylsulfinyl, isopropylsulfinyl. n-butylsulfinyl, isobutyl controlling weeds, in particular in crop plants, which are safer sulfinyl, sec-butylsulfinyl or tert-butylsulfinyl, preferably to crop plants (i.e. exhibit less phytotoxicity). methylsulfinyl or ethylsulfinyl. 0002 Protoporphyrinogen oxidase inhibiting herbicides 0013 Alkylsulfonyl is, for example, methylsulfonyl, eth are known in the art. However, these herbicides can exhibit ylsulfonyl, propylsulfonyl, isopropylsulfonyl. n-butylsulfo unacceptable levels of phytotoxicity in crop plants. There nyl, isobutylsulfonyl, sec-butylsulfonyl or tert-butylsulfonyl, exists a need therefore to provide improved herbicidal com preferably methylsulfonyl or ethylsulfonyl. positions which exhibit reduced crop phytotoxicity—and it has now been discovered that certain N-acylsulfamoylpheny 0014 Cycloalkyl groups preferably have from 3 to 6 ring lurea safeners—hitherto not taught in combination with these carbon atoms and may be substituted by one or more methyl herbicides—are surprisingly effective in Safening these com groups; they are preferably unsubstituted, for example cyclo pounds in crop plants. propyl, cyclobutyl, cyclopentyl or cyclohexyl. 0015. In a preferred embodiment of the present invention 0003. Thus, according to the present invention there is the protoporphyrinogen oxidase inhibiting herbicide is provided a herbicidal composition comprising: selected from the group consisting of flumioxazin, Sulfentra 0004 (i) a protoporphyrinogen oxidase inhibiting herbi Zone and fomesafen (including fomesafen-Sodium). In an cide selected from the group consisting flumioxazin, Sulfen especially preferred embodiment the protoporphyrinogen traZone, butafenacil and a diphenyl ether selected from the oxidase inhibiting herbicide is fomesafen (or fomesafen-So group consisting of acifluorfen (including aciflurofen-So dium). dium), fomesafen (including fomesafen-Sodium), lactofen 0016 Safeners of Formula (II) are known from EP-A- and oxyfluorfen: or an agronomically acceptable salt of said 365484. In a preferred embodiment the safener of is of For herbicide; and mula (II)in which R" is C-C alkoxy, preferably methoxy; R' 0005 (ii) a safener of Formula (II): is C-C alkyl, preferably methyl and R is hydrogen or methyl. In a particularly preferred embodiment the safener is 1-4-(N-2-methoxybenzoylsulfamoyl) phenyl-3-methy (II) O lurea. O H 0017. The herbicide: safener ratio in the herbicidal com A position may vary depending on the exact nature of the N-S N intended application. Typically the ratio will be from 100:1 to 1:100 on a weight for weight basis, preferably from 100:1 to Ra ? O y-N-R 1:50, more preferably from 25:1 to 1:25. 4 0018. The herbicidal compositions of the present inven tion will typically be formulated using in the art recognised formulation adjuvants, such as carriers, solvents and Surface 0006 or an agronomically acceptable salt of said com active agents (SFAS). Thus, the present invention further pro pound, wherein: vides a herbicidal composition further comprising an agricul 0007 R is selected from the group consisting of halogen, turally acceptable formulationadjuvant. The composition can nitro, C-C alkyl, C-Chaloalkyl, C-Chaloalkoxy, C-C, be in the form of concentrates which are diluted prior to use, cycloalkyl, phenyl, C-C alkoxy, cyano, C-C alkylthio. although ready-to-use compositions can also be made. The C-C alkylsulfinyl, C-C alkylsulfonyl, C-C alkoxycarbo final dilution is usually made with water, but can be made nyl and C-C alkylcarbonyl; and instead of, or in addition to, water, with, for example, liquid I0008 RandR are independently selected from the group fertilisers, micronutrients, biological organisms, oil or Sol consisting of hydrogen, C-C alkyl, C-C cycloalkyl, C-C, VentS. alkenyl and C-C alkynyl. 0019. The compositions can be chosen from a number of 0009 Halogen encompasses fluorine, chlorine, bromine formulation types, many of which are known from the or iodine. The same correspondingly applies to halogen in the Manual on Development and Use of FAO Specifications for context of other definitions, such as haloalkyl. Haloalkyl Plant Protection Products, 5th Edition, 1999. These include groups are thus, for example, fluoromethyl, difluoromethyl, dustable powders (DP), soluble powders (SP), water soluble trifluoromethyl, chloromethyl, dichloromethyl, trichlorom granules (SG), water dispersible granules (WG), wettable ethyl, 2.2.2-trifluoroethyl 2-fluoroethyl, 2-chloroethyl, pen powders (WP), granules (GR) (slow or fast release), soluble tafluoroethyl, 1,1-difluoro-2.2.2-trichloroethyl, 2.2.3,3-tet concentrates (SL), oil miscible liquids (OL), ultra low volume rafluoroethyl and 2.2.2-trichloroethyl and heptafluoro-n- liquids (UL), emulsifiable concentrates (EC), dispersible propyl. concentrates (DC), emulsions (both oil in water (EW) and 0010 Alkoxy is, for example, methoxy, ethoxy, propoxy, water in oil (EO)), micro-emulsions (ME), Suspension con isopropoxy, n-butoxy, isobutoxy, Sec-butoxy or tert-butoxy, centrates (SC), Suspo-emulsions (SE), aerosols, capsule Sus preferably methoxy and ethoxy. pensions (CS) and seed treatment formulations. 0011 Haloalkoxy is, for example, fluoromethoxy, difluo 0020. The herbicidal composition of the present invention romethoxy, trifluoromethoxy, 2.2.2-trifluoroethoxy, 1.1.2.2- may further comprise at least one additional pesticide, for tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2-dif example a nematicide, an insecticide, a fungicide and/or a US 2014/0O87947 A1 Mar. 27, 2014 herbicide. Examples of suitable pesticides are listed in “The 0031 (i) a protoporphyrinogen oxidase inhibiting herbi Pesticide Manual, Fourteenth Edition (2006), Editor, C. D. cide selected from the group consisting flumioxazin, Sulfen S. Tomlin. Preferably, the additional pesticide is one or more traZone, butafenacil and a diphenyl ether selected from the herbicides selected from the group consisting of , group consisting of acifluorfen (including aciflurofen-so , cafentraZone-ethyl, fluthiacet, flumiclorac, dium), fomesafen (including fomesafen-Sodium), lactofen , S-metolachlor, , , pyroxasul and oxyfluorfen: or an agronomically acceptable Salt of said fone, flufenacet, , dimethenamid-P bromoxy herbicide; and nil, , , , , diuron, 0032 (ii) a safener of Formula (II): , clethodim, fenoxaprop, haloxyflop, benSulfuron, nicosulfuron, rimsulfuron, primisulfuron, thifensulfuron, foramsulfuron, chlorSulfuron, halosulfuron, imaziquin, (II) , imaZapic, imaZethapyr, imaZamox, O iodosulfuron, metsulfuron, mesosulfuron sulfosulfuron tri O H floxysulfuron tribenuron methyl, , thiazopyr. A , cloranSulam-methyl, flucarbazone, flumetSulam N-S N amicarbaZone, thiencarbazone, chlorimuron-ethyl, , Re H/ || ( N-R 2,4-D, 2,4-DB, , diflufenzopry, tirclopry, , O ) , and ; or agrochemically O RC acceptable salts thereof. 0021. In a particular embodiment the herbicidal composi 0033 or an agronomically acceptable salt of said com tion does not comprise a herbicidal compound of Formula (I): pound, wherein: 0034) R' is selected from the group consisting of halogen, nitro, C-C alkyl, C-Chaloalkyl, C-Chaloalkoxy, C-C, (I) cycloalkyl, phenyl, C-C alkoxy, cyano, C-C alkylthio. C-C alkylsulfinyl, C-C alkylsulfonyl, C-C alkoxycarbo nyl and C-C alkylcarbonyl; and I0035) RandR are independently selected from the group consisting of hydrogen, C-C alkyl, C-C cycloalkyl, C-C, R5 / alkenyl and C-C alkynyl. O N R6 0036 Controlling means killing, reducing or retarding V M growth or preventing or reducing germination. Generally the O OS-N plants to be controlled are unwanted plants (weeds). Locus O Y. means the area in which the plants are growing or will grow. 0037 Components (i) and (ii) can be independently 0022 or an agronomically acceptable salt of said com applied to the locus pre-planting, pre-emergence and/or post pound, wherein: emergence. By “pre-planting it is meant that the herbicidal composition is applied before the crop is planted at the locus, 0023 R' is methyl or NH: by “pre-emergence it is meant that the herbicidal composi 0024 R is C-C, haloalkyl: tion is applied before the germinating crop plant seed emerges 0025 R is hydrogen of halogen; above the locus Surface and by “post-emergence it is meant I0026 R is halogen or cyano; that the herbicide composition is applied once the crop plant I0027 R is selected from the group consisting of hydro is visible above the locus surface. Component (ii) may also be gen, cyano, C-C alkyl, C-C alkoxy, C-C alkoxy-C- applied to the seed of the crop plant as a seed treatment prior Calkyl, C-C-7 cycloalkyl, C-Calkenyl, C-C alkynyl and to sowing. Such seed treatment has added utility in that it benzyl which is optionally substituted by halogen and/or helps protect the seed from any residual herbicide of Formula C-C alkyl; and (I) which may be present at the locus, for example from I0028. RandR are independently selected from the group previous applications of herbicide to the locus. Thus, in pre consisting of hydrogen, C-C alkyl, C-C alkoxy, C-C, ferred embodiments of the described method seeds treated alkenyl, C-C alkynyl, C-C, cycloalkyl, C-C, cycloalk with component (ii) are sown at the locus, followed by the enyl, phenyl and benzyl, wherein each of the eight above application of component (i) optionally combined with an mentioned substituents is optionally substituted by one to six additional component (ii) application. Alternatively, compo halogen atoms and/or by one, two or three groups selected nents (i) and (ii) will be applied to the locus in a single from: OH, NH, CN, CONH2, C-C alkoxy, C-C, combined pre or post-emergence application. haloalkoxy, C-C alkylthio, C-C haloalkylthio. 0038. The rates of application of components (i) and (ii) C-C alkylsulfonyl, C-C haloalkylsulfonyl, C-C alky will vary depending on the particular application (e.g. method lamino, di(C-C-alkyl)amino, formyl, C-C alkylcarbonyl, of application (pre- or post-emergence; seed dressing; appli C-C alkoxycarbonyl, C-C alkylaminocarbonyl, di(C-C, cation to the seed furrow; no tillage application etc.), the crop alkyl)aminocarbonyl, C-C cycloalkyl, phenyl and benzyl. plant, the weed(s) to be controlled, the prevailing climatic 0029. The herbicidal composition applied to the locus may conditions, and other factors governed by the method of also further comprise an additional herbicide safener. application, the time of application and the target crop). Typi 0030 The present invention still further provides a method cally, the rate of application of herbicide (i) will be from 10 to of selectively controlling weeds at a locus comprising crop 4000 gha, suitably from 10 to 2500 g/ha, more suitably from plants and weeds, wherein the method comprises application 50 to 500 g/ha. The rate of application of the safener compo to the locus of a weed controlling amount of: nent (ii) is suitably from 5 to 500 g/ha, more suitably from 10 US 2014/0O87947 A1 Mar. 27, 2014

to 100 g/ha. If the safener is to be applied as a seed treatment, four replications. Fomesafen (as ReflexTM) is applied pre then it can suitably be applied from 0.1 to 10 g safener per kg emergence (after planting) using a backpack sprayer. Herbi seed—typically 1 g safener per kg seed. cidal damage to the emerged wheat plants is assessed and the 0039. The application is generally made by spraying the results obtained are summarized in Table 1 below. These composition, typically by tractor mounted sprayer for large results indicate that the safener applied provides highly effec areas, but other methods such as dusting (for powders), drip or tive safening of the diphenyl ether herbicide fomesafen, even drench can also be used. at the highest application rate tested of 560 g/ha. 004.0 Useful plants in which the composition according to the invention can be used include crops such as cereals, for TABLE 1 example barley and wheat, cotton, oilseed rape, Sunflower, maize, rice, soybeans, Sugar beet, Sorghum, Switch grass and % Phytotoxicity Sugar cane. Maize, along with wheat, are however particu Fomesafen Safener A larly preferred. Crop plants can also include turf and trees, Rate g?ha Control Treated Seed Such as fruit trees, palm trees, coconut trees or other nuts. Also Ogiha O O included are vines such as grapes, fruit bushes, fruit plants 70 g/ha O O and vegetables. It should be understood that the crop plants 140 g/ha 1 O also include those which have been genetically engineered so 280 g?ha 18 O as to be tolerant to one or more additional herbicides, insects, 560 g/ha 71 O fungal, bacterial and/or viral infections. Examples are crop plants which comprise glyphosate tolerant 5-enol-pyru vylshikimate-3-phosphate synthase (EPSPS) (for example as Experiment 2 disclosed in U.S. Pat. No. 5,804,425, U.S. Pat. No. 6,566, 587), glyphosate N-acetyl transferase (GAT) (for example as 0043. A greenhouse study is performed to evaluate the disclosed in WO02/036782), herbicide tolerant 4-hydroxy safener response of various maize varieties to various PPGO pyruvyldioxgenase (HPPD) (for example as disclosed in inhibiting herbicides. Seeds from various maize varieties WO02/.46387), phosphinothricin acetyl transferase (PAT) (LEXXOR, PACTOL, CLAXXON, GARLAND and SUN (for example as disclosed in U.S. Pat. No. 5.273,894), cyto DANCE) are treated with either safener A (1-4-(N-2-meth chrome P450 (for example as disclosed in WO 07/103567), oxybenzoylsulfamoyl)phenyl-3-methylurea) or benoxacor glutathione S-transferase (GST) (for example as disclosed in at a rate of 1 g safener/kg of seed. Control seed is also WO01/21770), herbicide tolerant acetyl-COA-carboxylase included in the test which contains no safener seed treatment. (ACCase), herbicide tolerant acetolactate synthase (ALS) Herbicide treatments are applied pre-emergence, at the indi (for example as disclosed in U.S. Pat. No. 5,013,659), herbi cated application rates, using a laboratory tracksprayer with a cide tolerant protoporphyrinogen oxidase (PPGO) (for TeeJet 11002VS nozzle. The sprayer is set to deliver an output example as disclosed in WO95/34659), nitrilase of 200 L/ha by applying an air pressure of 2 bar. The treated (for example, as disclosed in WO89/00193), herbicide toler and control seeds are then planted in the treated Sandy loam ant phytoene desaturase (for example as disclosed in soil contained in 10 cm deep plastic trays and watered from EP03.93690), aryloxyalkanoate dioxygenase (for example as the top of the trays as needed. Herbicidal damage to the disclosed in WO2005/107437 and WO2007/053482) and emerged maize plants is then assessed 8 days after application dicamba degrading enzymes (for example as disclosed in (DAA) of the herbicide and the results obtained are summa WO98/45424); including known mutagenised or otherwise rized in Table 2 below (averaged values across the various modified variants of these polypeptides. maize lines used are provided). These results indicate that 0041. The compositions can be used to control unwanted safener A provides highly effective safening of the various plants (collectively, weeds). The weeds to be controlled PPGO inhibiting herbicides tested with particularly good may be both monocotyledonous species, for example Agros safening observed against SulfentraZone. tis, Alopecurus, Avena, Bromus, Cyperus, Digitaria, Echi nochloa, Lolium, Monochoria, Rottboelia, Sagittaria, Scir pus, Setaria, Sida and Sorghum, and dicotyledonous species, for example Abutilon, Amaranthus, Chenopodium, Chrysan Rate themum, Conyza, Galium, Ipomoea, Nasturtium, Sinapis, Product gai?ha untreated Benoxacor Safener A Solanum, Stellaria, Veronica, Viola and Xanthium. Weeds can Fomesafen - Reflex 31.25 O 1 O (SL240) 62.5 7 17 2 also include plants which may be considered crop plants but 125 36 34 19 which are growing outside a crop area (escapes), or which 250 74 73 51 grow from seed left over from a previous planting of a differ 500 86 88 69 ent crop (Volunteers). Such volunteers or escapes may be Fumioxazin - Valor 15.625 7 7 4 tolerant to certain other herbicides. (WG51) 31.25 25 12 7 62.5 31 32 14 125 48 43 34 BIOLOGICAL, EXAMPLES 250 70 53 51 SulfentraZone - Authority 31.25 1 O 1 Experiment 1 (SC500) 62.5 5 O O 125 10 9 2 0042 Winter wheat seed is treated with safener A (1-4- 250 51 55 7 (N-2-methoxybenzoylsulfamoyl)phenyl-3-methylurea) at 500 73 89 9 Butafenacil (WG71.4) 125 21 27 10 100 g safener/100 kg of seed. Control seed is also included 250 36 37 11 which contains no safener seed treatment. The wheat seed is 500 65 63 32 then planted in a field as a randomized block design including US 2014/0O87947 A1 Mar. 27, 2014

-continued or an agronomically acceptable salt of said compound, wherein: Rate R" is selected from the group consisting of halogen, nitro, Product gai?ha untreated Benoxacor Safener A C-C alkyl, C-Chaloalkyl, C-Chaloalkoxy, C-C, 1OOO 92 88 53 cycloalkyl, phenyl, C-C alkoxy, cyano, C-C alky 2OOO 98 97 76 lthio, C-C alkylsulfinyl, C-C alkylsulfonyl, C-C, Acifluorfen - Blazer 312.5 3 9 7 alkoxycarbonyl and C-C alkylcarbonyl; and (SL188.6) 625 24 22 24 12SO 56 60 47 R” and R are independently selected from the group con 2SOO 81 75 71 sisting of hydrogen, C-C alkyl, C-C cycloalkyl, SOOO 92 92 81 C-C alkenyl and C-C alkynyl. Lactofen - Cobra 312.5 15 18 13 (EC240) 625 27 25 23 2. A herbicidal composition accordingly to claim 1, 12SO 44 51 40 wherein the protoporphyrinogen oxidase inhibiting herbicide 2SOO S4 63 52 is selected from the group consisting flumioxazin, Sulfentra SOOO 66 61 53 Zone, and fomesafen (including fomesafen-sodium). Oxyfluorfen - Goal 125 44 47 26 (EC240) 250 67 66 50 3. A herbicidal composition according to claim 1, wherein 500 85 81 72 diphenyl ether herbicide is fomesafen (including fomesafen 1OOO 95 90 85 Sodium). 2OOO 98 95 91 4. A herbicidal composition according to claim 1, wherein the safener is a compound of Formula (II) wherein: 1. A herbicidal composition comprising: R" is C-C alkoxy; (i) a protoporphyrinogen oxidase inhibiting herbicide R’ is C-C alkyl; and Selected from the group consisting flumioxazin, Sulfen R is hydrogen. traZone, butafenacil and a diphenyl ether selected from 5. A herbicidal composition according to claim 1, further the group consisting of acifluorfen (including acifluro comprising at least one additional pesticide. fen-Sodium), fomesafen (including fomesafen-Sodium), 6. A method of selectively controlling weeds at a locus lactofen and oxyfluorfen: or an agronomically accept comprising crop plants and weeds, wherein the method com able salt of said herbicide; and prises application to the locus of a weed controllingamount of (ii) a safener of Formula (II): a herbicidal composition according to claim 1. 7. A method according to claim 6, wherein the crop plants are selected from the group consisting of barley, oats, Sor (II) ghum, wheat, cotton, maize, rice, Switchgrass and Sugarcane. O 8. A method according to claim 7, wherein the crop plant is O H wheat or maize. 9. A method according to claim 6, wherein component (ii) N-S N is applied as a seed treatment to the crop plant prior to Sowing. Re H/ O|| ) N-R 10. A method according to claim 6, whereincomponents (i) and (ii) are applied to the locus as a single, pre-emergence O RC application.