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US008298.992B2

(12) United States Patent (10) Patent No.: US 8,298,992 B2 Stern et al. (45) Date of Patent: Oct. 30, 2012

(54) LOW ODOR, LOW VOLATILITY SOLVENT (56) References Cited FOR AGRICULTURAL CHEMICALS U.S. PATENT DOCUMENTS (75) Inventors: Alan J. Stern, Magnolia, TX (US); 2,778,826 A * 1/1957 Schmidle ...... 546,192 David Ferguson, Spring, TX (US); 3,074,940 A * 1/1963 Benzing ...... 544,178 Howard Stridde, George West, TX (US) 3,342,673 A * 9, 1967 Kaufman et al...... 514,443 5,283,229 A 2/1994 Narayanan et al. (73) Assignee: Huntsman Petrochemical LLC. The 2005, 0137091 A1 6, 2005 Herold et al. Woodlands, TX (US) 2005/0215433 A1 9, 2005 Benitez et al. (*) Notice: Subject to any disclaimer, the term of this OTHER PUBLICATIONS patent is extended or adjusted under 35 Masuyama A. Preparation and Surface Active Properties of Terminal U.S.C. 154(b) by 743 days. Type of Alcohol Ethoxylates, Jun. 1989, JAOCS, vol. 66, No. (21) Appl. No.: 12/300,482 6, pppp. 834-837.* * cited by examiner (22) PCT Filed: May 25, 2007 86) PCT No.: PCT/US2007/069793 Primary Examiner — Brian-Yong S Kwon (86) O Assistant Examiner — Andriae M Holt S371 (c)(1), (74) Attorney, Agent, or Firm — Huntsman International (2), (4) Date: Nov. 12, 2008 LLC

(87) PCT Pub. No.: WO2007/140332 (57) ABSTRACT PCT Pub. Date: Dec. 6, 2007 A composition includes an agricultural component in an (65) Prior Publication Data amount of at least about 27% by weight and a solvent com position in an amount not greater than about 55% by weight. US 2009/0181850 A1 Jul 16, 2009 The solvent composition includes an amide having a structure of Formula I: Related U.S. Application Data (60) Provisional application No. 60/809,100, filed on May 26, 2006. O (I) (51) Int. Cl. ul - R2 AOIN 43/40 (2006.01) R. N. AOIN 43/44 (2006.01) R3 AOIN 43/36 (2006.01) (52) U.S. Cl...... 504/130; 514/65; 514/237.5; 514/317; 514/423 wherein R comprises a C to Cs hydrocarbon group, and (58) Field of Classification Search ...... so4/320, wherein R, and Rs comprise a C, or higher hydrocarbon 504/130; 54.4/106; 546/184: 548/500: 514/65, group. 514/237.5, 317,423 See application file for complete search history. 18 Claims, No Drawings US 8,298.992 B2 1. LOW ODOR, LOW VOLATILITY SOLVENT FOR AGRICULTURAL CHEMICALS

CROSS-REFERENCE TO RELATED APPLICATION(S) This application is the National Phase Of International Application PCT/US2007/069793 filed May 25, 2007 which wherein R comprises a C to Cs hydrocarbon group, and designated the U.S. and claims priority to U.S. Utility Provi wherein R and R comprise a C or higher hydrocarbon sional Patent Application No. 60/809,100, filed May 26, 10 group. 2006, entitled “LOW ODOR, LOW VOLATILITY SOL In a further exemplary embodiment, a composition VENT FOR AGRICULTURAL CHEMICALS. naming includes an agricultural component and a morpholine amide inventors Alan J. Stern, Dave Ferguson, and Howard Stridde, in an amount not greater than about 55% by weight of the which application is incorporated by reference herein in its 15 composition. The ratio of the amount of agricultural compo entirety. nent to the amount of morpholine amide is at least about 0.8. In another exemplary embodiment, a composition includes TECHNICAL FIELD an herbicidal component and a solvent composition including a morpholine amide component. This invention, in general, relates to solvents, and more In an additional embodiment, a composition includes an particularly to the field of organic solvents for pesticides. insecticidal component and a solvent composition including a morpholine amide component. BACKGROUND In another exemplary embodiment, a method of preparing an agricultural composition includes blending an amide Sol Solvents have typically been used in a preparation of agri 25 vent in an amount not greater than about 55% by weight with cultural chemical formulations. For example, organic Sol an agricultural component in an amount of at least about 27% vents were frequently used in various formulation types since by weight to form a solution and blending an emulsifier with at least the 1950s when pesticide products were first devel the solution. The amide solvent has a structure of oped and used on a large scale. However, many common solvents exhibit either high water solubility or poor solvency 30 of agricultural chemicals. O Those typical solvents that exhibit high water solubility provide an environmental risk when used in large quantities, us R2 Such as in agriculture. For example, such water soluble sol R y R3 vents may enter the water system, such as rivers, lakes, and 35 aquifers, contaminating water Supplies. On the other hand, those traditional solvents that have low wherein R comprises a C to Cs hydrocarbon group, and water solubility may also exhibit poor solvent characteristics where at R and R comprise a C or higher hydrocarbon with respect to particular agricultural chemicals. As such, a group. low ratio of agricultural chemicals to solvent is used, resulting 40 in a large quantity of Solvent being used to deliver a small DESCRIPTION OF THE PREFERRED quantity of an agricultural chemical. EMBODIMENT(S) Consequently, an improved organic solvent would be desirable. In a particular embodiment, an agricultural composition 45 includes an agricultural component and a solvent composi SUMMARY OF THE INVENTION tion. For example, the agricultural component may be a pes ticide. Such as an herbicide, plant growth regulator, an insec In a particular embodiment, a composition includes an ticide, or . The solvent composition NTF pesticide and a solvent composition in an amount not may include one or more solvents and, in particular, may greater than about 55% by weight. The solvent composition 50 include an amide solvent. For example, the amide solvent includes an amide having a structure of may be derived from a (e.g., C-C fatty acid) combined with an . In particular, the fatty acid amide may include a morpholine fatty acid amide. O The composition may take the form of an emulsifiable 55 concentrate, water based emulsion, Suspo-emulsion, or ul R2 micro-emulsifiable concentrate. In particular, the agricultural R N composition may include an agricultural component, a sol R3 vent composition, and an emulsifier or emulsifier blend. In addition, the agricultural composition may include a second wherein R comprises a C to Cs hydrocarbon group, and 60 agricultural component in the form of a liquid or Solid. wherein R and R comprise a C or higher hydrocarbon The agricultural component may be a pesticide. In an group. exemplary embodiment, the pesticide includes a fungicide, a In another exemplary embodiment, a composition includes bactericide, an herbicide, a plant growth regulator, an insec an agricultural component in an amount of at least about 27% ticide, or an insect growth regulator. In an example, the fun by weight and a solvent composition in an amount not greater 65 gicide may include an aliphatic fungicide, an amide than about 55% by weight. The solvent composition includes fungicide, an antibiotic fungicide, an aromatic fungicide, a an amide having a structure of benzimidazole fungicide, a benzimidazole precursor fungi US 8,298.992 B2 3 4 cide, a benzothiazole fungicide, a bridged diphenyl fungicide, In another example, a dicarboximide fungicide may a fungicide, a conazole fungicide, a dicarboximide include famoxadone; fluoroimide; chlozolinate; dichloZo fungicide, a dinitrophenol fungicide, dithiocarbamate fungi line; iprodione; isovaledione, mycloZolin; procymidone; Vin cide, an imidazole fungicide, a morpholine fungicide, an cloZolin; captafol; captan; ditalimfos; folpet; thiochlorfen organophosphate fungicide, an oxathiin fungicide, an phim; or any combination thereof. In a further example, a oxazole fungicide, a pyridine fungicide, a pyrimidine fungi dinitrophenol fungicide may include binapacryl; dinobuton; cide, a pyrrole fungicide, a quinoline fungicide, a quinone dinocap: dinocap-4; dinocap-6; dinocton, dinopenton; dino fungicide, a quinioxaline fungicide, a thiazole fungicide, a sulfon; dinoterbon; DNOC; or any combination thereof. In an thiocarbamate fungicide, a thiophene fungicide, a triazine additional example, a dithiocarbamate fungicide may include fungicide, a triazole fungicide, a urea fungicide, or another 10 azithiram; carbamorph, cufraneb, cuprobam, disulfiram; fer bam; metam; nabam; tecoram; thiram: Ziram; dazomet; etem; fungicide, or any combination thereof. milineb; mancopper, mancoZeb; maneb, metiram; polycar In an example, the aliphatic nitrogen fungicide may bamate; propineb, Zineb; or any combination thereof. include butylamine; cymoxanil; dodicin; dodine; guazatline; In an additional example, an imidazole fungicide may iminoctadine; or any combination thereof. In a further 15 include cyaZofanid; fenamidone; fenapanil; glyodin; iprodi example, an amide fungicide may include carpropamid; chlo one; isovaledione; pefurazoate; traZoxide; or any combina raniformethan; cyaZofamid; cyflufenamid; diclocymet; tion thereof. In another example, a morpholine fungicide may ethaboxam, fenoxanil; flumetover, furametpyr; prochloraZ; include aldimorph; benzamorph; carbamorph; dimetho quinazamid; silthiofam; triforine; benalaxyl; benalaxyl-M; morph; dodemorph; fempropimorph; flumorph; tridemorph; furalaxyl: metalaxyl: metalaxyl-M; pefurazoate; benzohy or any combination thereof. droxamic acid, tioxymid; thrichlamide; Zarilamid; Zoxamide; In another example, an organophosphate fungicide may cyclaburamid; furmecyclox dichlofluanid; tolylfluanid; include ampropylfos; ditalimfos; edifenphos; fosetyl; hexy benthiavalicarb; iprovalicarb; benalaxyl; benalaxyl-M; bos lthiofos; iprobenfos; phosdiphen; pyrazophos; tolclofoS-me calid; carboxin; fenhexamid; metSulfovax, ofurace; oxadixyl; thyl; triamiphos; or any combination thereof. In a further oxycarboxin; pyracarbolid; thifluzamide: tiadinil; benodanil; 25 example, an oxathlin fungicide may include carboxin; oxy flutolanil; mebenil; melpronil; salicylanilide; tecloftalam carboxin; or any combination thereof. In an additional fenfuram; furalaxyl; furcarbanil; methfuroxam; flusulfa example, an oxazole fungicide may include chloZolinate; mide; or any combination thereof. dichloZoline; draZOXolon; famoxadone; hymexaZol; meta In a further example, an antibiotic fungicide may include ZOXolon; mycloZolin, oxadixyl; Vinclozalin; or any combina aureofungin; blasticidin-S, cycloheximide; griseofulvin; 30 tion thereof. In an additional example, a pyridine fungicide kasugamycin; natamycin; polyoxins; polyoxorim; Strepto may include boscalid; buthiobate; dipyrithione; fluazinam; mycin; validamycin; azoxystrobin; dimoxystrobin: fluoxas pyridinitril; pyrifenox; pyroxychlor; pyroxyfur, or any com trobin, kresoxim-methy; metominostrobin; orysastrobin; bination thereof. picoxystrobin, pyraclostrobin; trifloxystrobin; or any combi In a further example, a pyrimidine fungicide may include nation thereof. In another exemplary embodiment, an aro 35 bupirimate; cyprodinil, diflumetorim; dimethirimol; ethiri matic fungicide may include biphenyl; chlorodinitronaphtha mol; fenarimol; ferimZone; mepanipyrim, nuarimol; lene; chloroneb; chlorothalonil; cresol; dicloran; pyrimethanil; triarimol; or any combination thereof. In an hexachlorobenzene; pentachlorophenol; quintoZene; sodium additional example, a pyrrole fungicide may include fempi pentachlorophenoxide; tecnaZene; or any combination clonil; fludioxonil; fluoroimide; or any combination thereof. thereof. In an additional example, a benzimidazole fungicide 40 In another example, a quinoline fungicide may include ethox may include benomyl; ; chlorfenazole; cypenda youin; halacrinate, 8-hydroxyquinoline Sulfate; quinacetol; Zole; debacarb; fuberidazole; mecarbinzid; rabenzazole; thia quinoxyfen; or any combination thereof. Inafurther example, bendazole; or any combination thereof. In another example, a a quinone fungicide may include benquinox; chloranil; benzimidazole precursor fungicide may include furophanate; dichlone; dithianon; or any combination thereof. thiophanate; thiophanate-methyl; or any combination 45 In another example, a quinoxaline fungicide may include thereof. chinomethionat, chlorquinox; thioquinox; or any combina In an additional example, a benzothiazole fungicide may tion thereof. In a further example, a thiazole fungicide may include bentaluron; chlobenthiazone; TCMTB; or any com include ethaboxam, etridiazole; metSulfovax; octhillinone; bination thereof. In another example, a bridged diphenyl fun thiabendazole; thiadifluor; thifluzamide; or any combination gicide may include bithionol; dichlorophen; diphenylamine; 50 thereof. In an additional example, a thiocarbamate fungicides or any combination thereof. In a further example, a carbamate may include methasulfocarb; prothiocarb; or any combina fungicide may include benthiavalicarb; furophanate, iprov tion thereof. In a further example, a thiophene fungicide may alicarb; ; thiophanate; thiophanate-methyl; include ethaboxam; silthiofam; or any combination thereof. benomyl; carbendazim, cypendazole; debacarb; mecarbin In a further example, a triazine fungicide may include anila Zid; diethofencarb, iodopropynyl butylcarbamate; or any 55 Zine. In another example, a triazole fungicide may include combination thereof. In a further example, a conazole fungi bitertanol; fluotrimazole; triazbutil; or any combination cide may include climbazole; clotrimazole; imazalil; Oxpo thereof. In an additional example, a urea fungicide may conazole; prochloraZ; triflumizole; azaconazole; bromucona include bentaluron; pencycuron; quinaZamid; or any combi Zole; cyproconazole; diclobutraZol; difenoconazole; nation thereof. Another fungicide may include acibenzolar; diniconazole; diniconazole-M; epoxiconazole; etaconazole; 60 acypetacs; allyl alcohol benzalkonium chloride; benzamacril; fenbuconazole; fluguinconazole; flusilazole; flutriafol; fur bethoxazin; carvone; chloropicrin; DBCP dehydroacetic conazole; furconazole-cis hexaconazole; imibenconazole; acid diclomeZine; diethyl pyrocarbonate; fenaminosulf: femi ipconazole; metconazole, myclobutanil; penconazole; propi tropan; fenpropidin; formaldehyde furfural; hexachlorobuta conazole; prothioconazole; quinconazole; Simeconazole; diene; iodomethane; isoprothiolane; methyl bromide; methyl tebuconazole; tetraconazole; triadimefon; triadimenol; triti 65 ; metrafenone; nitrostyrene; nitrothal-isopro conazole; uniconazole; uniconazole-P; or any combination pyl OCH; 2 phenylphenol phthalide; piperalin; probenazole; thereof. produinazid, pyroquilon; sodium orthophenylphenoxide; US 8,298.992 B2 5 6 spiroxamine; Sultropen; thicyofen; tricyclazole; chitin; chito In an additional example, an antibiotic herbicide may san: 4-cumylphenol, 4-alpha-cumylphenol; or any combina include bilanafos. Other herbicides include aromatic acid tion thereof. herbicides. In an example, the fungicide may be a non-triazole func In another example, a benzoic acid herbicide may include tional (NTF) fungicide, including a fungicide other than a chloramben; dicamba; 2.3.6-TBA; tricamba; or any combi triazole fungicide and triazole-functional conazole fungi nation thereof. cides. Non-triazole functional compounds excludes those In an additional example, a pyrimidinyloxybenzoic acid compounds that include a triazole group. Furthermore, the herbicide may include bispyribac; pyriminobac; or any com pesticide may bean NTF pesticide, including NTF fungicide, bination thereof. Further, a pyrimidinylthiobenzoic acid her NTF bactericide, NTF herbicide, NTF plant growth regulator, 10 NTF , NTF insect growth regulator, or any combi bicide may include pyrithiobac. nation thereof. In particular, the inventors have discovered In a further example, a phthalic acid herbicide may include that particular solvent compositions exhibit advantageous chlorthal. In addition, a picolinic acid herbicide may include solvent properties for particular NTF pesticides and particu aminopyralid; clopyralid; picloram; or any combination thereof. lar classes of NTF pesticides. 15 For example, the herbicide may bean amide oranilide type In another example, a quinolinecarboxylic acid herbicide herbicide, a phenoxy type herbicide, a sulfonylurea type her may include quinclorac; quinmerac, or any combination bicide, an aryloxyalkanoic acid type herbicide, a cyclohex thereof. An arsenical herbicide may include cacodylic acid; anedione type herbicide, urethane type herbicides, CMA; DSMA; hexaflurate; MAA; MAMA; MSMA; potas isoxazolidinone type herbicide, pyridinyloxyacetic acid type sium arsenite; sodium arsenite; or any combination thereof. herbicide, or any combination thereof. In a particular embodi In a further example, a benzoylcyclolhexanedione herbi ment, the herbicide is an amide type herbicide or an anilide cide may include mesotrione; Sulcotrione; tefuryltrione; tem type herbicide, such as propanil. In another exemplary botrione; or any combination thereof. A benzofuranylalkyl embodiment, the herbicide is a phenoxy type herbicide, such sulfonate herbicide may include benfuresate; ethofumesate: as 2,4-dichlorophenoxyacetic acid (2,4-D acid). In a further 25 or any combination thereof. example, the composition may include a Sulfonylurea type Further, a carbamate herbicide may include asulam; car herbicide. Such as chlolosulfuron. In an additional example, boxazole; chlorprocarb; dichlormate; fenasulam; karbutilate: the herbicide may include an aryloxyalklanoic acid type her terbucarb; or any combination thereof. bicide. In another example, the herbicide may include a In addition, a carbanilate herbicide may include barban; cyclohexanedione oxime type herbicide. In a further 30 example, the herbicide may include a urethane type herbi BCPC; carbasulam; carbetamide; CEPC; chlorbufam; chlor cide, such as phenmediphan or desmediphan. In another propham; CPPC: desmedipham; phenisopham; phenme example, the herbicide may include an isoxazolidinone type dipham, phenmedipham-ethyl, propham; Swep; or any com herbicide. Such as clomaZone. In an additional example, the bination thereof. herbicide may include a pyridinyloxyacetic acid type herbi 35 In another example, a cyclohexene oxime herbicide may cide, such as triclopyr. Further, the herbicide may be selected include alloxydim; butroxydim; clethodim; cloproxydim; from an herbicide of the classes and subclasses listed below. cycloxydim; profoxydim; Sethoxydim; tepraloxydim; In an example, an amide type herbicide may include alli tralkoxydim; or any combination thereof. dochlor; beflubutamid; benzadox; benzipram; bromobutide: In a further example, a cyclopropylisoxazole herbicide cafenstrole; CDEA; cyprazole; dimethenamid; dimethena 40 may include isoxachlortole; isoxaflutole; or any combination mid-P, diphenamid; epronaZ: etnipromid; fentraZamide; thereof. flupoxam, fomesafen; halosafen; isocarbamid; isoxaben; In an additional example, a dicarboximide herbicide may napropamide; naptalam, pethoxamid; propyZamide; include benzfendizone: cinidon-ethyl; flumezin; flumiclorac: quinonamid; tebutam; or any combination thereof. flumioxazin; flumipropyn, or any combination thereof. In a further example, an anilide herbicide may include 45 Further, a dinitroaniline herbicide may include benfluralin; chloranocryl; cisanilide; clomeprop; cypromid; diflufenican; butralin; dinitramine; ethal fluralin; fluchloralin; isopropalin; etobenzanid; fenasulam; flufenacet; flufenican, mefenacet; methalpropalin: nitiralin; oryzalin; pendimethalin; prodi mefluidide; metamifop, monalide; naproanilide; pen amine; profluralin; trifluralin; or any combination thereof. tanochlor, picolinafen; propanil; or any combination thereof. In addition, a dinitrophenol herbicide may include In an additional example, an arylalanine herbicide may 50 dinofenate; dinoprop: dinosam; dinoseb; dinoterb; DNOC: include benzoylprop; flamprop; flamprop-M; or any combi etinofen; medinoterb; or any combination thereof. nation thereof. In a further example, adiphenyl herbicide may In another example, a chloroacetanilide herbicide may include ethoxyfen. Further, a nitrophenyl ether herbicide may include acetochlor; alachlor; butachlor; butenachlor; include acifluorfen: aclonifen; bifenox; chlomethoxyfen; delachlor; diethatyl; dimethachlor; metazachlor; meto 55 chlornitrofen: etnipromid; fluorodifen; fluoroglycofen; fluo lachlor; S-metolachlor; pretilachlor; propachlor; propisoch ronitrofen; fomesafen; furyloxyfen; halosafen; lactofen; lor; prynachlor; terbuchlor; thenylchlor; xylachlor; or any nitrofen; nitrofluorfen: oxyfluorfen: or any combination combination thereof. thereof. In an example, a Sulfonanilide herbicide may include ben In another example, a dithiocarbamate herbicide may Zofluor; cloranSulam; diclostulam, florasulam; flumetSulam; 60 include dazomet; metam; or any combination thereof. metoSulam, perfluidone; pyrimisulfan, profluaZol; or any In a further example, a halogenated aliphatic herbicide may combination thereof. include alorac, chloropon; dalapon; flupropanate; hexachlo In another example, a herbicide may include roacetone; iodomethane; methyl bromide; monochloroacetic asulam; carbasulam, fenasulam; oryzalin; penoXSulam; acid; SMA, TCA; or any combination thereof. pyroxSulam, or any combination thereof. 65 In an additional example, a imidazolinone herbicide may In a further example, a thioamide herbicide may include include imazamethabenz; imaZamox, imazapic; imazapyr; bencarbazone; chlorthiamid; or any combination thereof. imaZaquin; imazethapyr; or any combination thereof. US 8,298.992 B2 7 8 Further, a herbicide may include bromobonil; bro In an example, a chlorotriazine herbicide may include atra moxynil; chloroxynil; dichlobenil; iodobonil; ioxynil; pyra Zine; chlorazine; cyanazine; cyprazine; eglinazine; ipazine; clonil; or any combination thereof. mesoprazine; procyazine; proglinazine; propazine; Sebuthy In another example, an organophosphorus herbicide may lazine; simazine; terbuthlylazine; trietazine; or any combina include amiprofos-methyl; anilofos; ; bilanafos: tion thereof. butamifos; 2,4-DEP: DMPA: EBEP; fosamine; glufosinate: In another example, a methoxytriazine herbicide may glyphosate; piperophos; or any combination thereof. include atraton; methometon; prometon; secbumeton; sim In a further example, an oxadiazolone herbicide may eton; terbumeton; or any combination thereof. include dimefuron; methazole; oxadiargyl, oxadiaZon; or any In an additional example, a methylthiotriazine herbicide combination thereof. 10 may include ametryn; aZiprotryne; cyanatryn; desmetryn; In an additional example, a phenoxy herbicide may include dimethametryn; methoprotryne; prometryn; simetryn; ter bromofenoxim; clomeprop; 2,4-DEB; 2,4-DEP; difeno butryn; or any combination thereof. penten; disul; erbon: etnipromid; fenteracol; trifopsime; or In a further example, a triazinone herbicide may include any combination thereof. 15 ametridione; amibuzin; hexazinone; isomethioZin; In an example, a phenoxyacetic herbicide may include metamitron; metribuzin, or any combination thereof. 4-CPA; 2,4-D, 3,4-DA: MCPA: MCPA-thioethyl; 2,4,5-T; or In another example, a triazole herbicide may include ami any combination thereof. trole; cafenstrole, epronaZ; flupoxam, or any combination In another example, a phenoxybutyric herbicide may thereof. include 4-CPB: 2,4-DB: 3,4-DB: MCPB: 2,4,5-TB; or any In an example, a triazolone herbicide may include amicar combination thereof. baZone; bencarbazone; carfentraZone; flucarbazone; pro In an additional example, a phenoxypropionic herbicide poxycarbazone; SulfentraZone; thiencarbazone; or any com may include cloprop: 4-CPP; dichlorprop; dichlorprop-P: bination thereof. 3,4-DP, fenoprop; mecoprop; mecoprop-P, or any combina Further, a triazolopyrimidine herbicide may include clo tion thereof. 25 ranSulam, dicloSulam; floraSulam; flumetSulam; metoSulam; In a further example, an aryloxyphenoxypropionic herbi penoXSulam, pyroxSulam; or any combination thereof. cide may include chlorazifop, clodinafop; clofop, cyhalofop; In addition, a uracil herbicide may include butafenacil; diclofop, fenoxaprop; fenoxaprop-P, fenthiaprop; fluazifop; bromacil; flupropacil; isocil; lenacil; terbacil; or any combi fluazifop-P; haloxyfop; haloxyfop-P; isoxapyrifop; metami nation thereof. fop; propaquizafop; quizalofop; quizalofop-P; trifop, or any 30 In another example, aurea herbicide may include benzthia combination thereof. Zuron; cumyluron; cycluron; dichloralurea; diflufenZopyr; In another example, a phenylenediamine herbicide may isonoruron; isouron; methabenzthiaZuron; monisouron; include dinitramine; prodiamine; or any combination thereof. noruron; or any combination thereof. Further, a pyrazole herbicide may include azimsulfuron; In a further example, a phenylurea herbicide may include difenZoquat; halosulfuron; metaZachlor; pyrazosulfuron; 35 anisuron; buturon; chlorbromuron; chloreturon; chlorotolu pyroxasulfone; or any combination thereof. ron; chloroXuron; daimuron; difenoXuron; dimefuron; diu In addition, a benzoylpyrazole herbicide may include ben ron; fenuron; fluometuron; fluothiuron; isoproturon; linuron; Zofenap; pyrasulfotole; pyrazolynate; pyrazoxyfen; topram methiuron; methyldymron; metobenzuron; metobromuron; eZone; or any combination thereof. metoxuron; monolinuron; monuron; neburon; parafluron; In another example, a phenylpyrazole herbicide may 40 phenobenzuron; Siduron; tetrafluron; thidiaZuron; or any include fluaZolate; nipyraclofen; pyraflufen, or any combina combination thereof. tion thereof. Further, the herbicide may be a sulfonylurea herbicide. For In a further example, a pyridazine herbicide may include example, a pyrimidinylsulfonylurea herbicide may include credazine; pyridafol; pyridate; or any combination thereof. amidosulfuron; azim Sulfuron; benSulfuron; chlorimuron; In an additional example, a pyridaZinone herbicide may 45 cyclosulfamuron; ethoxysulfuron; flaZaSulfuron; flucetosul include brompyrazon; chloridazon; dimidazon; flufenpyr; furon; flupyrsulfuron; foramsulfuron; halosulfuron; imaZo metflurazon; norflurazon, oxapyrazon; pydanon; or any com Sulfuron; mesosulfuron; nicosulfuron; orthosulfamuron: Oxa bination thereof. Sulfuron; primisulfuron; pyrazosulfuron; rimsulfuron; Further, a pyridine herbicide may include aminopyralid: sulfometuron; sulfosulfuron; trifloxysulfuron; or any combi cliodinate; clopyralid; dithiopyr; fluroxypyr; haloxydine; 50 nation thereof. In addition, a triazinylsulfonylurea herbicide picloram, picolinafen; pyriclor; pyroxSulam; thiazopyr; tri may include chlorSulfuron; cinosulfuron; ethametSulfuron; clopyr; or any combination thereof. iodosulfuron; metsulfuron; prosulfuron; thifensulfuron; tria In addition, a pyrimidinediamine herbicide may include sulfuron; tribenuron; triflusulfuron; tritosulfuron; or any iprymidam, tioclorim; or any combination thereof. combination thereof. In an example, a quaternary ammonium herbicide may 55 In another example, thiadiazolylurea herbicides may include cyperquat; diethamquat; difenZoquat, diduat; mor include buthiuron; ethidimuron; tebuthiuron; thiazafluron; famduat; paraquat, or any combination thereof. thidiaZuron; or any combination thereof. In another example, a thiocarbamate herbicide may include In a further example, an unclassified herbicide may include butylate; cycloate; di-allate; EPTC; esprocarb; ethiolate; iso acrolein; allyl alcohol; azafenidin; benazolin; bentaZone; polinate; methiobencarb; molinate; orbencarb; pebulate; pro 60 benzobicyclon; buthidazole; calcium cyanamide; camben sulfocarb: pyributicarb; sulfallate; thiobencarb: tiocarbazil; dichlor; chlorfenac; chlorfemprop; chlorflurazole; chloflure tri-allate; vernolate; or any combination thereof. nol; cinmethylin; clomazone: CPMF; cresol; ortho-dichlo In another example, a thiocarbonate herbicide may include robenzene: dimepiperate; endothal; fluoromidine; fluridone; dimexano; EXD; proxan; or any combination thereof. flurochloridone; flurtamone; fluthiacet; indanofan; methyl Further, a thiourea herbicide may include methiuron. In 65 isothiocyanate; OCH; oxaziclomefone; pentachlorophenol; addition, a triazine herbicide may include dipropetryn; triazi pentoxazone; phenylmercury acetate; pinoxaden; prosulfa flam; trihydroxytriazine; or any combination thereof. lin; pyribenzoxim; pyriftalid; quinoclamine; rhodethanil; US 8,298.992 B2 9 10 Sulglycapin; thidiazimin; tridiphane; trimeturon; tripropin ethyl-DDD: HCH; gamma-HCH; ; ; dan; tritac.; or any combination thereof. pentachlorophenol; TDE; ; bromocyclen; chlorbicy In a further exemplary embodiment, the agricultural com clen; ; ; ; dilor, ; ponent may include an insecticide. For example, the agricul ; HEOD; ; HHDN: isobenzan; isodrin; kele tural component may include an antibiotic insecticide, a van; ; or any combination thereof. botanically-derived insecticide, a carbamate insecticide, a In a further exemplary embodiment, the organophosphate dinitrophenol insecticide, a formamide insecticide, a fumi insecticide may include bromfenvinfos; : gant insecticide, an insect growth regulator, a crotoxyphos; ; ; dimethylvinphos; fos analogue, an organochlorine insecticide, an organophosphate pirate; heptenophos; methocrotophos; ; monocro insecticide, an oxadiazine insecticide, a phthalimide insecti 10 tophos; ; naftalofos; ; propaphos: cide, a pyrazole insecticide, a insecticide, a pyri ; TEPP; ; dioxabenzofos; fosme midinamine insecticide, a pyrrole insecticide, a tetronic acid thilan; ; acethion; amiton; cadusafos, chlore insecticide, a thiourea insecticide, a urea insecticide, among thoxyfos; chlormephos; ; demephion-O; deme others, or any combination thereof. For example, an antibiotic phion-S; ; demeton-O; demeton-S; demeton-methyl: insecticide may include allosamidin; thuringiensin; ; 15 demeton-O-methyl; demeton-S-methyl; demeton-S-methyl abamectin; doramectin; emamectin, eprinomectin; ivermec sulplhon; ; ; ; IPSP; isothioate: tin: Selamectin; milbemectin; milbemycin oxime; moxidec malathionl; methacrifos; Oxydemeton-methyl, Oxydeprofos; tin, or any combination thereof. oxydisulfoton; ; ; terbulos; thiometon; In another example, a botanically-derived insecticide may amidithion; cyanthoate; ; ethoate-methyl; for include anabasine; ; d-; nicotine; pyre mothion; mecarbam; ; ; Sophamide; thrins cinerins; cinerin I; cinerin II: jasmolin I; jasmolin II; vamidothion chlorphoxim; ; phoxim-methyl; azame I; pyrethrin II; quassia; rotenone; ryania sabadilla; thiphos; ; coumithoate; ; ; or any combination thereof. menaZOn; morphothion; ; pyraclofos; In a further embodiment, the carbamate insecticide may pyridaphenthion; quinothion; dithicrofos; thicrofos; azin include ; ; benfuracarb; ; car 25 phos-ethyl, azinphos-methyl; dialifos; , ; bosulfan; decarbofuran; furathiocarb; dimetan; ; Zolaprofos; chlorpraZophos; pyrazophos; , chlo hyduinicarb; ; alanycarb; ; aldoxycarb; rpyrifos-methyl; butathiofos; ; etrimfos: lirimfos: ; butoxycarboxim; ; nitrilacarb: pirimiphos-ethyl; pirimiphos methyl; primidophos; pyrimi ; taZimcarb; thiocarboxime; thiodicarb; ; tate; ; ; quinallphos-methyl; athi allyxycarb : bufencarb; butacarb; carbanolate; clo 30 dathion; lythidathion; ; prothidathion; isazofos: ethocarb; dicresyli; dioxacarb; EMPC; ; feneth triaZophos; azothoate; bromophos; bromophos-ethyl; car acarb; ; isoprocarb: : : mex bophenothion; chlorthiophos; ; cythioate; dicap acarbate; promacyl: ; , trimethacarb; thon; dichlofenthion; etaphos; famphur; fenchlorphos; femi XMC; xylylcarb; or any combination thereof. trothion; fensulfothion; ; fenthion-etlhyl: In an additional embodiment, the dinitrophenol insecticide 35 heterophos: jodfenphos; mesulfenfos; ; parathion may include dinex; dinoprop; dinosam; DNOC: cryolite; methyl; phenkapton; phosnichlor; ; prothiofos; Sodium hexafluorosilicate; sulfluramid; or any combination sulprofos; temephos; trichlorimetaphos-3; trifenofos; buto thereof. nate; trichlorfon, mecarphon; ; trichloronat: In another exemplary embodiment, the formamide insec cyanofenphos; EPN. : crufomate; ; fos ticide may include : ; ; 40 thietan; mephosfolan, phosfolan, pirimetaphos; : ; or any combination thereof. In an additional isocarbophos; isofenphos; ; propetamphos: embodiment, the fumigant insecticide may include acryloni , mazidox, ; or any combination thereof. trile; carbon ; ; chloroform; In an additional embodiment, the oxadiazine insecticide chloropicrin; para-dichlorobenzene, 1,2-dichloropropane; may include . In a further embodiment, the phthal ethyl formate; ethylene dibromide; ethylene dichloride; eth 45 insecticide may include dialifos; phosmet, tet ylene oxide, hydrogen cyanide; iodomethane; methyl bro ramethrin; or any combination thereof. In an example, the mide; methylchloroform; methylene chloride; naphthalene; pyrazole insecticide may include acetoprole; ethiprole; phosphine; Sulfuryl fluoride; tetrachloroethane; or any com ; ; tolfenpyrad; Vaniliprole; or any com bination thereof. bination thereof. In a further exemplary embodiment, the insect growth 50 In an additional embodiment, the pyrethroid insecticide regulators may include bistrifluron; ; chlorfluazu may include ; allethrin; ; barthrin; ron; ; ; flucycloXuron; flufenoXu ; bioethanomethrin; cyclothrin; cycloprothrin; ron; hexaflumuron; ; novaluron, noviflumuron; ; beta-cyfluthrin; ; gamma-cyhalothrin; penfluron, teflubenZuron; triflumuron; epolfenonane; fenoxy lambda-cyhalothrin; ; alpha-cypermethrin; carb; ; kinoprene; , ; tri 55 beta-cypermethrin; theta-cypermethrin; Zeta-cypermethnn; prene; juvenile hormone I; juvenile hormone II; juvenile hor ; ; dimefluthrin; dimethrin; mone III; chromafenozide; halofenozide; methoxyfenozide: ; fenfluthrin; fempirithrin; fempropathrin; fenval tebutenozide, C.-ecdysone; ecdysterone; diofenolan; pre erate; ; flucythrinate; fluvalinate; tau-fluvali cocene I; precocene II; precocene III; dicyclanil; or any com nate; furethrin; ; ; ; bio bination thereof. 60 pennethrin; transpermethnn; ; ; In another exemplary embodiment, the nereistoxin ana profluthrin; pyresmethrin; ; bioresimethrin; cis logue may include benSultap; cartap; thiocyclam; thiosultap: methrin; ; terallethrin; ; ; flonicamid; ; , ; thia : ; flufenprox; halfenprox; protrifen methoxam, ; ; nitenpyram; bute; ; or any combination thereof. In another ; or any combination thereof. 65 example, the pyrimidinamine insecticide may include flufen In an additional embodiment, the organochlorine insecti erim; pyrimidifen; or any combination thereof. In a further cide may include bromo-DDT; camphechlor; DDT, pp'-DDT; example, the pyrrole may include . US 8,298.992 B2 11 12 In an additional example, the tetronic acid insecticide may combinations thereof. In another example, R and R may include spiromesifen, the thiourea insecticide may include form a ring hydrocarbon group selected from the group con diafenthiuron, and the urea insecticide may include flucofu sisting of —CH2CHOCH2CH2—, —CH2CH2CHCH . ron; sulcofuron; or any combination thereof. Other insecti and —CH2CH2CH2CH2CH2—. cides may include closantel; clorpyrifos, crotamiton; EXD; In an exemplary embodiment, the amide solvent may be fenaZaflor; fenoxacrim; , isoprothiolane; formed through reaction of a fatty acid with an amine. In a malonoben, metoxadiaZone; nifluridde; pyridaben; pyridalyl; particular example, the amine is di-substituted, which may rafoxanide; triarathene; triazamate; or any combination result in a liquid amide derivative. For example, the amine thereof. may include diallyl or ring structures, such as mor In a particular example, the insecticide may include a pyre 10 pholine, dimethylamine, diethylamine, dibutylamine, diiso throid insecticide. For example, a pyrethroid type insecticide propylamine, pyrrolidine, piperidine, or any combination may be a cypermethrin orbifenthrin insecticide. thereof. The desired may also be prepared from other The agricultural composition may include the agricultural raw materials including and acid halides. component in an amount between about 0.5% and about 95% In a particular embodiment, the amide solvent is a morpho by weight, such as greater than about 25% by weight, or at 15 line amide, Such as an amide derived from a fatty acid and least about 27% by weight based oil the total organic compo morpholine. For example, the morpholine amide may con sition of the agricultural composition, excluding water. For form to the structure of Formula II. example, the agricultural composition may include at least about 35% by weight of the agricultural component, such as at least about 38% by weight, or at least about 40% by weight (II) of the agricultural component. The agricultural composition includes the agricultural component and a solvent composition. In an exemplary embodiment, the solvent composition includes one or more 25 ~OO Solvents. In particular, the solvent composition includes an amide solvent having a structure according to Formula I. In a further example, the amide solvent may be a dialkyl amide solvent, Such as a dimethylamide solvent, diethyla (I) O mide solvent, dipropylamide solvent, or any combination 30 thereof, such as illustrated in Formula III. R ul - R V R3 (III) 35 In an example, R may be a hydrocarbon group. Such as a C. to Cs hydrocarbon group. For example, R may be a C, C or less hydrocarbon group. In another example, R may include a Cs to C hydrocarbon group, such as a C7 to Co hydrocarbon group. Alternatively, R may be a Cs to C 40 In a particular embodiment, the amide solvent has a melt hydrocarbon group. In an embodiment, R may include a ing point not greater than about 20° C. Such as not greater hydrocarbon group. Such as an group, an unsaturation, than about 15°C., or even not greater than about 10°C. In an one or more heteroatom, an aromatic ring system, a Saturated exemplary embodiment, the amide solvent has a molecular ring system, a second amide group, or any combination weight between about 150 and 270. In particular, the amide thereof. 45 solvent may have a molecular weight between about 170 and In an embodiment in which the amide is formed through 240. reaction of a fatty acid with an amine, R may be derived from In addition, the amide solvent may exhibit low water solu a single fatty acid or a blend of fatty acids. For example, the bility and desirable solvency properties. For example, the fatty acids may include a short or medium chain fatty acid. amide solvent may be soluble in water to an amount not Embodiments include C-C acids, such as C-C acids, 50 greater than about 2 wt %, such as not greater than about 1.5 Co-Co acids, or even Cs-Co acids, or alternatively C-C, wt %, or even not greater than about 1.0 wt %. In particular, acids, or any combinations thereof. An example of a Suitable the amide solvent may be soluble in water to an amount not short chain fatty acid includes hexanioic, octanoic, decanoic greater than about 5000 ppm. acid, or any combination thereof. In a particular embodiment, In addition, the solvent composition may include other the amide solvent is formed from a blend offatty acids within 55 Solvents, such as alkylbenzenes, alkyl naphthalenes, methyl the ranges above. esters of fatty acids, aliphatic hydrocarbons, cycloaliphatic In an embodiment, R or Rs may independently include hydrocarbons, fuel oils, isophorone, methyl ethyl , alkyl groups, amine groups, ether groups, or any combination N-methylpyrolidone, butyl lactate, dimethyl , thereof. In a particular embodiment, R or Rs may indepen acetophenone, or any combination thereof. In general, any dently include an , such as a methyl, ethyl, propyl. 60 Solvent or solvents that provide homogenous solutions when or , or any combination thereof. In a further used in combination the amide solvent may be used. example, the R or Rs may form a ring incorporating the Inaparticular embodiment, a solvent composition includes nitrogen of the amide. For example, RandR may act to form a significant amount of the amide solvent. In an example, the a morpholine group, a Saturated ring, an unsaturated ring, a solvent composition may include at least about 50% by pyrrolidine group, or a piperidine group. In particular, R or 65 weight of the amide solvent based on the weight of the solvent R independently may be a hydrocarbon group selected from composition. For example, the solvent composition may the group consisting of methyl, ethyl, propyl, butyl, and any include at least about 75% of the amide solvent, such as at US 8,298.992 B2 13 14 least about 90% by weight, or even at least about 95% by Many suitable emulsifiers are available from Huntsman weight of the amide solvent based on the weight of the solvent Petrochemical Corporation under the tradenames Surfonic R, composition. In a particular embodiment, the solvent compo Nansa R, TermulR), or any combination thereof. sition consists essentially of the amide solvent, such as In particular, the emulsifier blend may be included in an amount not greater than about 50% by weight based on the including about 100% by weight of the amide solvent based total organic composition, excluding water. For example, the on 1 the weight of the solvent composition. In a further emulsifier or emulsifier blend may be included in an amount example, the solvent composition is Substantially free of not greater than about 35% by weight, such as not greater than water. In an exemplary embodiment, a solvent composition about 20% by weight, not greater than about 15% by weight, includes a second solvent in an amount not greater than about not greater than about 10% by weight, or even as low as 5% by 75% by weight, Such as an amount not greater than about 10 weight or lower based on the total composition weight, 50%, not greater than about 25%, not greater than about 15%, excluding water. The amount of emulsifier included in the not greater than 10% by weight, or not greater than about 5% agricultural composition is typically driven by the type of by weight. In a particular example, the solvent composition is agricultural composition or the desired performance of the agricultural composition. substantially free of a solvent other than the amide solvent. In 15 In an exemplary embodiment, a method for preparing an particular, the solvent composition may be a morpholine agricultural composition includes blending an amide solvent amide solvent. in an amount not greater than about 55% by weight of an Further, the solvent composition exhibits desirable sol agricultural component to form a solution. The amide solvent Vency relative to particular agricultural compositions or com may have a structure according to Formula I, wherein R ponents. For example, the solvency of the agricultural com comprises a C to Cs hydrocarbon group, and where an R. ponent in the Solvent composition may be expressed as a ratio and R comprise a C1 or higher hydrocarbon group. The of the highest amount of an agricultural component that dis method may further include blending an emulsifier with the Solves to the amount of solvent composition in an agricultural Solution. Further, other solvents or agricultural components may be blended with the solution to form the agricultural composition. In a particular embodiment, the ratio may be at composition. least about 0.5. In further example, the ratio may be at least 25 In a particular embodiment, the agricultural composition about 0.8, such as at least about 1.0, or even at least about 1.1. may be formed as an emulsifiable concentrate including the In an exemplary embodiment, the ratio may be less than about agricultural component, the amide solvent, and an emulsifier. 10, such as less than about 5. In a further example, the agricultural composition may be In an exemplary embodiment, the agricultural composition formed as a water-based emulsion. For example, a solution includes not greater than about 55% by weight of the solvent 30 including the amide solvent, an agricultural component, and composition based on the total weight of the organic compo emulsifiers may be blended with a portion of water. In a nents in the composition, excluding water. For example, the further exemplary embodiment, the agricultural composition composition may include not greater than about 50% by may be formed as a Suspo-emulsion, including Suspended weight of the Solvent composition, such as not greater than Solids within the solution of agricultural component, amide 35 Solvent, and emulsifiers. For example, an additional agricul about 45% by weight of the solvent composition. Further, the tural component may be included in solid form within the Solvent composition may be included in the agricultural com Solution to form the Suspo-emulsion. Further, the agricultural position in an amount of at least about 5% by weight based on composition may be formulated as a micro-emulsifiable con the total weight of the organic components in the agricultural Centrate. composition, excluding water. For example, the solvent com 40 Particular embodiments of the above composition exhibit position may be included in an amount of at least about 10% advantageous technical features relative to typical agricul by weight, such as at least about 20% by weight, at least about tural compositions. For example, the agricultural composi 25% by weight, or even at least about 30% by weight. tion exhibits low odorand low volatile organic carbon content In addition, the agricultural composition may include an (low VOC content), such as when measured by the California emulsifier or an emulsifier blend. For example, the emulsifier 45 VOC-TGA analytical method, EPA Reference Method 24. may include an anionic calcium, sodium, or amine neutral Further, solvent compositions including the amide solvent ized linear alkylsulfonate type Surfactant, a phosphate of exhibit lower toxicity and more facile bidegradation when nonionic Surfactant, cationic tallow amine Surfactant, non compared to traditional Solvents. Such solvent compositions ionic Surfactant, or any combination thereof. An example of exhibit low water solubility, low toxicity, low odor, higher an anionic Surfactant includes the alkali metal, alkaline earth 50 flash point, low volatility, while simultaneously exhibiting or amine salt of dodecyl benzene Sulphonic acid or another higher solvency for particular agricultural components. alkylarylsulphonic acid, sodium dialkyl Sulphosuccinate, In a particular example, a morpholine derivative of a fatty Such as Sodium diisoctylsulphosuccinate, an amine salt of an acid amide exhibits desirable solvency for agricultural com ether Sulphate, or any combination thereof. ponents such as propanil, bifenthrin, 2,4-D acid, delta An example of a nonionic Surfactant includes a condensa 55 methrin, clomaZone, or any combination thereof. tion product of a fatty acid ester, a linear or branched fatty alcohol, a fatty amine with ethylene or propylene oxide, an EXAMPLES alkyl-, alkenyl, or polyaryl-substituted phenol with ethylene or propylene oxide, a fatty ester of a polyhydric alcohol ester Example 1 (e.g., a sorbitan fatty acid ester), a condensation product of 60 Such an ester with ethylene oxide (e.g., polyoxyethylene Sor An amide solvent is formed from “C-810' fatty acid, which bitan fatty acid ester), a block copolymer of ethylene oxide is a light cut fatty acid commercially available from Proctor & and propylene oxide, an ethoxylated lanolin alcohol, an Gamble. “C-810” includes 3-5 wt.% C fatty acid, 53-60 wt. ethoxylated lanolin acid, or any combination thereof. An % Cs fatty acid, 34-42 wt.% Cofatty acid, and 0-2 wt.% C. example of a cationic Surfactant includes, for example, an 65 fatty acid. The “C-810 is reacted with morpholine to form acetate or oleate of aliphatic mono-, di- or polyamines, or any the amide solvent, referred to herein as “C-810 morpholine combination thereof. Anionic/inionionic blends may be used. amide solvent.” US 8,298.992 B2 15 Morpholine (552 g. 6.35 moles) and “C810” (978 g. 6.35 TABLE 2 moles) are placed in a 3-liter glass reactor equipped with an overhead stirrer and a Dean-Stark trap for removing water. Propanil EC The mixture is heated to 150° C. and is stirred for 6 hours, during which time the reaction bi-product (water) is continu Propanil, technical 45% ously removed by means of the Dean-Stark trap. After water C-810 morpholine amide solvent 40% ceases to be collected, an additional amount of morpholine is Emulsifier blend 15% added to the reactor (approximately 52 g, 0.6 moles). The temperature is held at 150° C. for 2 additional hours with stirring. The temperature is raised to 170° C. and the remain 10 TABLE 3 ing morpholine, if any, is removed by passing agentle stream of nitrogen through the reactor for a period of 2 hours before Chlorosurfuron EC cooling to ambient temperature. Chlorsulfuron, technical 190 C-810 morpholine amide solvent 89% 15 Emulsifier blend 10% Example 2

The C-810 morpholine amide solvent is mixed with the TABLE 4 following components to form a herbicide emulsifiable con centrate (propanil EC): propanil, technical 45 wt.%: morpho Cypermethrin EC line amide 43 wt.%; and emulsifier blend 12 wt.%. Cypermethrin, technical 44% C-810 morpholine amide solvent 44% Emulsifier blend 12% Example 3 25

A series of experiments are performed to determine an TABLE 5 amount of an agricultural component to be included in an emulsifiable concentrate without recrystallization of the agri Bifenthrin EC cultural component. Table 1 illustrates the highest test 30 Bifenthrin, technical 25% amount of agricultural component that dissolves in the Sol C-810 morpholine amide solvent 67% vent composition at approximately 25°C. The amount that Emulsifier blend 8% dissolves is determined through blending an amount of the agricultural component with the solvent composition and an emulsifier blend, and storing the resulting solution at 0°C. for 35 TABLE 6 2 weeks. If no crystal growth is observed, the amount is determined to have dissolved. 2,4-D acid EC 2,4-D acid, technical 40% Table 1 illustrates the parts agricultural component, the C-810 morpholine amide solvent 48% pairs solvent composition, and the ratio of the parts agricul Emulsifier blend 12% tural component to the parts solvent composition. In this 40 example, the solvent composition is the C-810 morpholine amide solvent. TABLE 7

TABLE 1. 45 Phenmediphan & Desmediphan EC Solvency of Agricultural Component (AC) Phenmediphan 10% Desmediphan 10% Agricultural Solvent C-810 morpholine amide solvent 70% Agricultural Component Composition Ratio Emulsifier blend 10% Component (parts) (parts) (AC:solvent) 50

Propanil 45 40 1.12 TABLE 8 Chlorsulfuron 1 89 O.O1 Cypermethrin 44 44 1.O Clomazone EC Bifenthrin 25 67 0.37 55 2,4-D acid 40 48 O.83 Clomazone, technical 45% 1:1 Phenmediphant 2O 70 O.28 C-810 morpholine amide solvent 45% Desmediphan Emulsifier blend 10% Clomazone 45 45 1.O Triclopyr 4 86 O.04 Alachlor 50 50 1.O 60 TABLE 9 Triclopyr EC Example agricultural compositions are formed based on the highest tested amount of agricultural component to dis Triclopyr, technical 4% C-810 morpholine amide solvent 86% solve in the solvent composition as determined above. Such 65 Emulsifier blend 10% example agricultural compositions are provided in Tables 2-9. Amounts are expressed in weight percent. US 8,298.992 B2 17 18 TABLE 10 The invention claimed is: 1. A composition comprising: Fluoxastrobin EC a non-triazole functional pesticide; and a solvent composition in an amount not greater than about Fluoxastrobin 3% 55% by weight, the solvent composition including an C-810 morpholine amide solvent 89% amide having a structure of Emulsifier blend 8%

10 O TABLE 11 R ul y R R3 Alachlor EC 15

Allochlor 45% wherein R is a C to Cs hydrocarbon group selected from C-810 morpholine amide solvent 45% the group consisting of —CHCHOCH2CH , —CH2CH2CHCH . and Emulsifier blend 10% —CHCHCHCHCH , and wherein R and R. form a ring hydrocarbon group. 2. The composition of claim 1, wherein R comprises an TABLE 12 alkyl group. 3. The composition of claim 1, wherein R and R form a Cypermethrin EC 25 morpholine group, a saturated ring, an unsaturated ring, a pyrrolidine group, or a piperidine group. Cypermethrin 44% 4. The composition of claim 1, wherein the amide is C-810 morpholine amide solvent 22% derived from C-C fatty acids. Aromatic 150 (ExxonMobil) 22% 30 5. The composition of claim 1, wherein the amide com Emulsifier blend 12% prises a morpholine amide. 6. The composition of claim 1, wherein the amount of solvent composition is not greater than about 50% by weight TABLE 13 of the composition. 35 Propanil EC 7. The composition of claim 1, wherein a ratio of the amount of the non-triazole functional pesticide to the amount Propanil 40% C-810 morpholine amide solvent 30% of the solvent composition is at least about 0.5. Propylene carbonate (Huntsman) 15% 8. The composition of claim 7, wherein the ratio is at least Emulsifier blend 15% 40 O8. 9. The composition of claim 1, wherein the solvent com position includes at least 50% by weight of the amide based Example 5 on the weight of the solvent composition. 10. The composition of claim 1, wherein the solvent com 45 position is substantially free of water. The C-810 morpholine amide solvent is tested to determine water solubility. The water solubility is compared with solu 11. The composition of claim 1, wherein the amide has a bility data available for a dimethyamide. water solubility not greater than about 2.0 wt %. 12. The composition of claim 1, comprising greater than TABLE 13 50 about 25% by weight of the non-triazole functional pesticide. 13. The composition of claim 1, wherein the non-triazole Water Solubility functional pesticide is an amide or anilide type herbicide. Solvent Solubility in Water (wt %) 14. The composition of claim 1, wherein the non-triazole C-810 morpholine amide solvent <1% 55 functional pesticide comprises a pyrethroid type insecticide. N,N-dimethyldecanamide 3.8% 15. The composition of claim 1, wherein the non-triazole functional pesticide is included in the amount of at least 27% by weight. The above-disclosed subject matter is to be considered 16. The composition of claim 1, wherein the solvent com illustrative, and not restrictive, and the appended claims are 60 intended to cover all Such modifications, enhancements, and position is included in an amount of at least 10% by weight. other embodiments, which fall within the true scope of the 17. A method of preparing an agricultural composition, the present invention, Thus, to the maximum extent allowed by method comprising: law, the scope of the present invention is to be determined by blending an amide solvent in an amount not greater than the broadest permissible interpretation of the following 65 about 55% by weight with an agricultural component in claims and their equivalents, and shall not be restricted or an amount of at least 27% by weight to form a solution, limited by the foregoing detailed description. the amide solvent having a structure of US 8,298.992 B2 19 20 —CH2CH2CHCH . and O —CHCHCHCHCH , and wherein R and R. ul R form a ring hydrocarbon group; and R N1 2 blending an emulsifier with the solution. Y. 5 18. The method of claim 17, wherein the amide solvent is 3 a morpholine amide solvent. wherein R is a C to Cs hydrocarbon group selected from the group consisting of —CH2CH2OCH2CH2—, k . . . . UNITED STATES PATENT AND TRADEMARK OFFICE CERTIFICATE OF CORRECTION PATENT NO. : 8,298.992 B2 Page 1 of 1 APPLICATIONNO. : 12/300.482 DATED : October 30, 2012 INVENTOR(S) : Stern et al. It is certified that error appears in the above-identified patent and that said Letters Patent is hereby corrected as shown below:

In the Claims:

Column 18, Claim 1, Lines 17-20, delete “selected from the group consisting of -CH2CH2OCH2CH2-, - CH2CH2CH2CH2-, and -CH2CH2CH2CH2CH2 and insert -- selected from the group consisting of -CH2CH2OCH2CH2-, -CH2CH2CH2CH2-, and -CH2CH2CH2CH2CH2--- after “ring hydrocarbon group' therefor; Columns 19, Lines 9-10, Column 20, Lines 1-2, Claim 17, delete “selected from the group consisting of -CH2CH2OCH2CH2-, -CH2CH2CH2CH2-, and -CH2CH2CH2CH2CH2 and insert -- Selected from the group consisting of -CH2CH2OCH2CH2-, -CH2CH2CH2CH2-, and -CH2CH2CH2CH2CH2--- after “ring hydrocarbon group therefor.

Signed and Sealed this Twenty-second Day of October, 2013

Teresa Stanek Rea Deputy Director of the United States Patent and Trademark Office