OA17275A

OA17275A - Herbicidal compositions comprising 4-amino -3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3methoxyphenyl) pyridine-2-carboxylic acid.

Info

Publication number: OA17275A
Application number: OA1201500024
Authority: OA
Inventors: Carla N. YERKES; Norber SATCHIVI; Richard K. Mann; Nelson M. CARRANZA GARZON; Monte R. WEIMER
Original assignee: Dow Agrosciences Llc
Priority date: 2012-07-24
Filing date: 2013-07-19
Publication date: 2016-04-29

Abstract

Provided herein are synergistic herbicidal compositions containing and methods utilizing (a) a compound of formula (I)

Description

HERBICIDAL COMPOSITIONS COMPRISING 4-AMINO-3-CHLORO-5-FLUORO-6-(4CHLORO-2-FLUORO-3-METHOXYPHENYL) PYRIDINE-2-CARBOXYLIC ACID .

Priority Claim

This application claims the benefit of United States provisional patent application number 61/675,103 filed on July 24, 2012 and United States patent application number 13/839,043 filed on March 15, 2013, the disclosure of each of which is incorporated herein by reference in its entirety.

Field

Provided herein are herbicidal compositions comprising and methods of controlling undesirable végétation utilizing (a) 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3methoxyphenyl)pyridine-2-carboxylic acid or an agriculturally acceptable ester or sait thereof and (b) an acetyl-CoA carboxylase (ACCase) inhibitor.

Background

The protection of crops from weeds and other végétation which inhibit crop growth is a constantly recurring problem in agriculture. To help combat this problem, researchers in the field of synthetic chemistry hâve produced an extensive variety of chemicals and chemical formulations effective in the control of such unwanted growth. Chemical herbicides of many types hâve been disclosed in the literature and a large number are in commercial use. However, there remains a need for compositions and methods that are effective in controlling undesirable végétation.

Summary

A first embodiment includes herbicidal compositions, comprising: a herbicidally effective amount of (a) a compound of the formula (I)

or an agriculturally acceptable sait or ester thereof: and (b) ACCase inhibitors, or a sait or ester thereof.

A second embodiment includes a composition of according to the first embodiment, wherein (a) is a Cm alkyl or benzyl ester of compound (I).

A third embodiment includes a composition of according to the first embodiment wherein (a) is a benzyl ester of compound (I).

A fourth embodiment includes a composition of according to the first embodiment wherein (a) is the compound of formula (I), which is the carboxylic acid.

A fifth embodiment includes compositions of the first, second, third, or fourth embodiments, wherein (b) is selected from the group consisting of: clethodim, clodinafoppropargyl, cyhalofop-R-butyl, diclofop-methyl, fenoxaprop-P-ethyl, fluazifop-P-butyl, haloxyfop-R-methyl, metamifop, pinoxaden, profoxydim, quizalofop-P-ethyl, sethoxydim or tralkoxydim.

A sixth 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 clethodim.

A seventh 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 clodinafoppropargyl.

An eighth 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 cyhalofop-Rbutyl.

A ninth embodiment includes a composition ofthe first embodiment, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is diclofop-methyl.

A tenth 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 fenoxaprop-Pethyl.

An eleventh 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 fluazifop-Pbutyl.

A twelfth 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 haloxyfop-Rmethyl.

A thirteenth 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 metamifop.

A fourteenth 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 pinoxaden.

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.

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-Pethyl.

A seventeenth embodiment includes a composition of the first embodiment, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) sethoxydim.

An eighteenth 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 tralkyoxydim.

A nineteenth embodiment includes composition according to the first through the eighteenth embodiments further comprising a herbicide safener.

A twentieth embodiment includes a composition according to the first embodiment wherein the ratios the compound of formula (I) or agriculturally acceptable sait or ester thereof to clethodim or an agriculturally acceptable sait or ester thereof, expressed in units of weight to weight (g to g), gae/ha to gai/ha, or gae/ha to gae/ha, are within the range of about 1:140 to about 9:1, from about 1:35 to about 2.2:1 and from about 1:9 to about 1:8.

A twenty-first embodiment includes a composition according to the first embodiment wherein the ratios the compound of formula (I) or agriculturally acceptable sait or ester thereof to clodinafop-propargyl or an agriculturally acceptable sait or ester thereof, expressed in units of weight to weight (g to g), gae/ha to gai/ha, or gae/ha to gae/ha, are within the range of about 1:40 to about 60:1, from about 1/6 to about 2:3 and from about 1:3 to about 1:4.

A twenty-second embodiment includes a composition according to the first embodiment wherein the ratios the compound of formula (I) or agriculturally acceptable sait or ester thereof to cyhalofop-R-butyl or an agriculturally acceptable sait or ester thereof, expressed in units of weight to weight (g to g), gae/ha to gai/ha, or gae/ha to gae/ha, are within the range of about 1:155 to about 6:1, from about 1:34 to about 1:2, from about 1:10 to about 1:70,4:1,0.5:1,1:7 and about 1:9.

A twenty-third embodiment includes a composition according to the first embodiment wherein the ratios the compound of formula (I) or agriculturally acceptable sait or ester thereof to diclofop-methyl or an agriculturally acceptable sait or ester thereof, expressed in units of weight to weight (g to g), gae/ha to gai/ha, or gae/ha to gae/ha, are within the range of about 1:560 to about 5:1, from about 1:140 to 1:9 and 1:35.

A twenty-fourth embodiment includes a composition according to the first embodiment wherein the ratios the compound of formula (I) or agriculturally acceptable sait or ester thereof to fenoxaprop-P-ethyl or an agriculturally acceptable sait or ester thereof, expressed in units of weight to weight (g to g), gae/ha to gai/ha, or gae/ha to gae/ha, are within the range of about 1:170 to about 30:1, from about 1:16 to about 4:1, from about 0.4:1 to about 0.6:1,0.25:1 and 0.6:1 and the crop safeners isoxadifen-methyl and mefenpyr-diethyl are incorporated into the product.

A twenty-fifth embodiment includes a composition according to the first embodiment wherein the ratios the compound of formula (I) or agriculturally acceptable sait or ester thereof to fluazifop-P-butyl or an agriculturally acceptable sait or ester thereof, expressed in units of weight to weight (g to g), gae/ha to gai/ha, or gae/ha to gae/ha, are within the range of about 1:210 to about 3:1, from about 1:41 to 0.8:1 and from about 1:10 to about 1:5.

A twenty-sixth embodiment includes a composition according to the first embodiment wherein the ratios the compound of formula (I) or agriculturally acceptable sait or ester thereof to haloxyfop-R-methyl or an agriculturally acceptable sait or ester thereof, expressed in units of weight to weight (g to g), gae/ha to gai/ha, or gae/ha to gae/ha, are within the range of about 1:45 to about 10:1, from about 1:6 to about 1:5, from about 0.65:1 and about 1.3:1.

A twenty-seventh embodiment includes a composition according to the first embodiment wherein the ratios the compound of formula (I) or agriculturally acceptable sait or ester thereof to metamifop or an agriculturally acceptable sait or ester thereof, expressed in units of weight to weight (g to g), gae/ha to gai/ha, or gae/ha to gae/ha, are within the range of about 1:150 to about 6:1, from about 1:34 to about 10:1, from about 1:2 to about 0.64:1, 0.6:1,1:1,1:4, and 3:1.

A twenty-eighth embodiment includes a composition according to the first embodiment wherein the ratios the compound of formula (I) or agriculturally acceptable sait or ester thereof to pinoxaden or an agriculturally acceptable sait or ester thereof, expressed in units of weight to weight (g to g), gae/ha to gai/ha, or gae/ha to gae/ha, are within the range of about 1:30 to about 150:1, from about 1:12 to about 2:1, from about 1:3 to about 1:2,2:1 and 1:2.

A twenty-ninth embodiment includes a composition according to the first embodiment wherein the ratios the compound of formula (I) or agriculturally acceptable sait or ester thereof to profoxydim or an agriculturally acceptable sait or ester thereof, expressed in units of weight to weight (g to g), gae/ha to gai/ha, or gae/ha to gae/ha, are within the range of about 1:70 to about 29:1, from about 1:23 to about 3:1, from about 3:1 to about 1:3, 0.35:1, 0.17:1,2.8:1 and 1,4:1.

A thirtieth embodiment includes a composition according to the first embodiment wherein the ratios the compound of formula (I) or agriculturally acceptable sait or ester thereof to quizalofop-P-ethyl or an agriculturally acceptable sait or ester thereof, expressed in units of weight to weight (g to g), gae/ha to gai/ha, or gae/ha to gae/ha, are within the range of about

1:100 to about 12:1, from about 1:8 to about 19:1,5:1,1.16:1, 0.6:1, 9:1,2.33:1 and 1.2:1.

A thirty-first embodiment includes a composition according to the first embodiment wherein the ratios the compound of formula (I) or agriculturally acceptable sait or ester thereof to sethoxydim or an agriculturally acceptable sait or ester thereof, expressed in units of weight to weight (g to g), gae/ha to gai/ha, or gae/ha to gae/ha, are within the range of about 1:70 to about 29:1, from about 1:62 to about 0.6:1, from about 13:1 to about 1:8.5,1:7.7,1:30.9,0.5:1 and 1:8.5.

A thirty-second embodiment includes a composition according to the first embodiment wherein the ratios the compound of formula (I) or agriculturally acceptable sait or ester thereof to tralkoxydim or an agriculturally acceptable sait or ester thereof, expressed in units of weight to weight (g to g), gae/ha to gai/ha, or gae/ha to gae/ha, are within the range of about 1:38 to about 60:1, from about 1:40 to about 0.6:1, from about 1:10 to about 1:6.3,1:3,1:6 and 1:1.5.

A thirty-third embodiment includes any composition according to the first through the thirty-second embodiments that, further comprising an agriculturally acceptable adjuvant, and/or carrier and/or herbicide safener.

A thirty-fourth embodiment includes any composition according to the first through the thirty-third embodiments, wherein synergy between herbicides is determined by the Colby équation.

A thirty-fifth embodiment includes any composition according to the first embodiment wherein (b) is cyhalofop-butyl or carboxylic acid, carboxylate sait, or ester thereof, wherein the composition further comprises penoxsulam, bentazon-sodium, triclopyr, bispyribac-sodium, imazamox, benzobicyclon, quinclorac, glyphosate, glufosinate, benfuresate, fentrazamide, indanofan, ipfencarbazone, mefenacet, oxazichlomefone, pretilachlor, propyrisulfuron, pyraclonil, pyriftalid, or pyrimisulfàn, or an agriculturally acceptable sait, carboxylic acid, carboxylate sait, or ester thereof, in combination as a synergistic 3 way/temary mixture.

A thirty-sixth embodiment includes any composition according to the first embodiment wherein (b) is fenoxaprop, metamifop, or profoxydim, or agriculturally acceptable sait, ester, carboxylate sait, or carboxylic acid thereof, wherein the composition further comprises penoxsulam, bentazon-sodium, triclopyr, bispyribac-sodium, imazamox, benzobicyclon, quinclorac, glyphosate, glufosinate, benfuresate, fentrazamide, indanofan, ipfencarbazone, mefenacet, oxazichlomefone, pretilachlor, propyrisulfuron, pyraclonil, pyriftalid, or pyrimisulfàn, or an agriculturally acceptable sait, carboxylic acid, carboxylate sait, or ester thereof, in combination as a synergistic 3 way/temary mixture.

A thirty-seventh embodiment includes methods for controlling undesirable végétation comprising the steps of contacting the végétation or the locus thereof with or applying to the soil or water to prevent the emergence or growth of végétation the at least one composition according to the first through the thirty-sixth embodiments.

A thirty-eighth embodiment includes methods for controlling undesirable végétation comprising the steps of contacting the végétation or the locus thereof with or applying to the soil or water to prevent the emergence or growth of végétation utilizing a herbicidally effective

amount of (a) a compound of the formula (I)
Fx	nh₂ . A. /Cl
	A Y A <A/0h N H
	_% 0
cr γ	F
H,c'⁰	(I)

or an agriculturally acceptable sait or ester of thereof, and (b) an ACCase inhibitor.

A thirty-ninth embodiment includes methods of the thirty-seventh and thirty-eighth embodiments, wherein the undesirable végétation is controlled in rice, cereals, wheat, barley, oats, rye, sorghum, com/maize, sugarcane, sunflower, oilseed râpe, canola, sugar beet, soybean, cotton, pineapple, pastures, grasslands, rangelands, fallowland, turf, tree and vine orchards, aquatics, plantation crops, vegetables, industrial végétation management (IVM) or rights of way (ROW).

A fortieth embodiment includes methods of the thirty-seventh and thirty-eighth embodiments wherein the undesirable végétation is immature.

A forty-first embodiment includes methods of the thirty-seventh and thirty-eighth embodiments wherein the compounds (a) and (b) are applied to water.

A forty-second embodiment includes methods according to the forty-first embodiment, wherein the water is part of a flooded rice paddy.

A forty-third embodiment includes methods according to the thirty-seventh and thirtyeighth embodiments, wherein compounds (a) and (b) are applied pre-emergently to the weed or crop.

A forty-fourth embodiment includes methods according to the thirty-seventh and thirtyeighth embodiments, wherein compounds (a) and (b) are applied post-emergently to the weed or crop.

A forty-fifth embodiment includes methods according to the thirty-seventh and thirtyeighth embodiments, wherein the undesirable végétation is controlled in glyphosate-, 5enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitor-, glufosinate-, glutamine synthetase inhibitor-, dicamba-, phenoxy auxin-, pyridyloxy auxin-, synthetic auxin-, auxin transport inhibitor-, aryloxyphenoxypropionate-, cyclohexanedione-, phenylpyrazoline-, acetyl CoA carboxylase (ACCase) inhibitor-, imidazolinone-, sulfonylurea-, pyrimidinylthiobenzoate-, triazolopyrimidine-, sulfonylaminocarbonyltriazolinone-, acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitor-, 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor-, phytoene desaturase inhibitor-, carotenoid biosynthesis inhibitor-, protoporphyrinogen oxidase (PPO) inhibitor-, cellulose biosynthesis inhibitor-, mitosis inhibitor-, microtubule inhibitor-, very long chain fatty acid inhibitor-, fatty acid and lipid biosynthesis inhibitor-, photosystem I inhibitor-, photosystem II inhibitor-, triazine-, or bromoxynil- tolérant crops.

A forty-sixth embodiment includes methods according to the forty-fifth embodiment, wherein the résistant or tolérant crop possesses multiple or stacked traits conferring résistance or tolérance to multiple herbicides or multiple modes of action.

A forty-seventh embodiment includes methods according to the thirty-seventh and thirtyeighth embodiments, wherein the undesirable végétation comprises a herbicide résistant or tolérant weed.

A forty-eighth embodiment includes methods according to the forty-seventh embodiment, wherein the résistant or tolérant weed is a biotype with résistance or tolérance to multiple herbicides, multiple chemical classes, or multiple herbicide modes-of-action or via multiple résistance mechanisms.

A forty-ninth embodiment includes methods according to the forty-seventh embodiment wherein the résistant or tolérant weed is a biotype résistant or tolérant to acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors, photosystem II inhibitors, acetyl CoA carboxylase (ACCase) inhibitors, synthetic auxins, auxin transport inhibitors, photosystem I inhibitors, 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, microtubule assembly inhibitors, fatty acid and lipid synthesis inhibitors, protoporphyrinogen oxidase (PPO) inhibitors, carotenoid biosynthesis inhibitors, very long chain fatty acid (VLCFA) inhibitors, phytoene desaturase (PDS) inhibitors, glutamine synthetase inhibitors, 4-hydroxyphenylpyruvate-dioxygenase (HPPD) inhibitors, mitosis inhibitors, cellulose biosynthesis inhibitors, herbicides with multiple modes-of-action, quinclorac, arylaminopropionic acids, difenzoquat, endothall, or organoarsenicals.

A fiftieth embodiment includes the composition according to any of embodiments 1-4, wherein the ratio of compound (a) to compound (b) is such that the composition exhibits synergy.

A fifty-first embodiment includes the composition according to any of embodiments 1-4 or 50, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to clethodim or agriculturally acceptable sait or ester thereof is from about 1:140 to about 9:1.

A fifty-second embodiment includes the composition according to any of embodiments 1-4 or 50, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to clodinafop-propargyl or agriculturally acceptable sait or ester thereof is from about 1:40 to about 60:1.

A fifty-third embodiment includes the composition according to any of embodiments 1-4 or 50, wherein the weight ratio of compound of formula (I) or agriculturally acceptable sait or ester thereof to cyhalofop-R-butyl or agriculturally acceptable sait or ester thereof is from about 1:155 to about 6:1.

A fifty-fourth embodiment includes the composition according to any of embodiments 14 or 50, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to diclofop-methyl or agriculturally acceptable sait or ester thereof is from about 1:560 to about 5:1.

A fifty-fifth embodiment includes the composition according to any of embodiments 1-4 or 50» wherein the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to fenoxaprop-P-ethyl of agriculturally acceptable sait or ester thereof is from about 1:170 to about 30:1, and the crop safeners isoxadifen-methyl and mefenpyr-diethyl are incorporated into the product.

A fifty-sixth embodiment includes the composition according to any of embodiments 1-4 or 50, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to fluazifop-P-butyl or agriculturally acceptable sait or ester thereof is from about 1:210 to about 3:1.

A fifty-seventh embodiment includes the composition according to any of embodiments 1-4 or 50, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to haloxyfop-R-methyl or agriculturally acceptable sait or ester thereof is from about 1:45 to about 10:1.

A fifty-eighth embodiment includes the composition according to any of embodiments 14 or 50, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to metamifop or agriculturally acceptable sait or ester thereof is from about 1:150 to about 6:1.

A fifty-ninth embodiment includes the composition according to any of embodiments 1-4 or 50, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to pinoxaden or agriculturally acceptable sait or ester thereof is from about 1:30 to about 150:1.

A sixtieth embodiment includes the composition according to any of embodiments 1-4 or 50, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to profoxydim or agriculturally acceptable sait or ester thereof is from about 1:70 to about 29:1.

A sixty-first embodiment includes the composition according to any of embodiments 1-4 or 50, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to quizalofop-P-ethyl or agriculturally acceptable sait or ester thereof is from about 1:100 to about 12:1.

A sixty-second embodiment includes the composition according to any of embodiments 1-4 or 50, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to sethoxydim or agriculturally acceptable sait or ester thereof is from about 1:70 to about 29:1.

A sixty-third embodiment includes the composition according to any of embodiments 1-4 or 50, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to tralkoxydim or agriculturally acceptable sait or ester thereof is from about 1:38 to about 60:1.

Provided herein are herbicidal compositions comprising a methods of controlling undesirable végétation utilizing a herbicidally effective amount of (a) a compound of the formula (I).

NH-,

Cl

OH or an agriculturally acceptable sait or ester of thereof, and (b) an ACCase inhibitor. Exemplary

ACCase inhibitors include, but are not limited to, clethodim, clodinafop-propargyl, cyhalofop-Rbutyl, diclofop-methyl, fenoxaprop-P-ethyl, fluazifop-P-butyl, haloxyfop-R-methyl, metamifop, pinoxaden, profoxydim, quizalofop-P-ethyl, sethoxydim or tralkoxydim. The compositions may also contain an agriculturally acceptable adjuvant or carrier.

Detailed Description

DEFINITIONS

As used herein, the compound of formula (I) has the following structure:

(IH)

The compound of formula (I) can be identified by the name 4-amino-3-chloro-6-(4-chloro-2fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylic acid and has been described in U.S. Patent 7,314,849 (B2), which is incorporated herein by reference in its entirety. Exemplary uses of the compound of the formula (I) include controlling undesirable végétation, including grass, broadleaf and sedge weeds, in multiple non-crop and cropping situations.

Without being limited to any theory, ACCase inhibitors believed to inhibit to any extent acetyl coenzyme A carboxylase (ACCase), an enzyme involved in fatty acid synthesis. Exemplary ACCase inhibitors include, but are not limited to aryloxyphenoxy propionates and the cyclohexanediones. Further examples include, but are not limited to, clethodim, clodinafoppropargyl, cyhalofop-R-butyl, diclofop-methyl, fenoxaprop-P-ethyl, fluazifop-P-butyl, haloxyfop-R-methyl, metamifop, pinoxaden, profoxydim, quizalofop-P-ethyl, sethoxydim and tralkoxydim.

As used herein, clethodim is 2-[l-[[[(2E)-3-chloro-2-propen-l-yl]oxy]imino]propyl]-5[2-(ethylthio)propyl]-3-hydroxy-2-cyclohexen-l-one and possesses the following structure:

This compound is described in Tomlin, C., ed. A World Compendium The Pesticide

Manuai. 15^th ed. Alton: BCPC Publications, 2009 (hereafter “The Pesticide Manuai, Fifteenth

Edition, 2009.”). Exemplary uses of clethodim include its use as a herbicide for, e.g., postemergence control of annual and perennial grasses in broadleaf crops, vegetables, trees and vines.

As used herein, clodinafop-propargyl is 2-propynyl (27?)-2-[4-[(5-chloro-3-fluoro-2pyridinyl)oxy]phenoxy]propanoate and possesses the following structure:

O

This compound is described in The Pesticide Manual, Fifteenth Edition, 2009.

Exemplary uses of clodinafop-propargyl inciude 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.

As used herein, cyhalofop-butyl is butyl (2R)-2-[4-(4-cyano-2fluorophenoxy)phenoxy]propanoate and possesses the following structure:

NC •3

This compound is described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of cyhalofop-butyl inciude its use as a herbicide for, e.g., post-emergence control of annual and perennial grass weeds in seeded and transplanted rice.

As used herein, diclofop-methyl is methyl 2-(4-(2,4dichlorophenoxy)phenoxy]propanoate and possesses the following structure:

Cl

This compound is described in The Pesticide Manual, Fifteenth Edition, 2009.

Exemplary uses of diclofop-methyl inciude its use as a herbicide for, e.g., post-emergence control of wild oats, wild millets, and other annual grass weeds in wheat, barley, rye, red fescue, and broadleaf crops.

As used herein, fenoxaprop-P-ethyl is ethyl (27?)-2-[4-[(6-chloro-2benzoxazolyl)oxy]phenoxy]propanoate and possesses the following structure:

O

This compound is described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of fenoxaprop-P-ethyl include its use as a herbicide for, e.g., control of annual and perennial grass weeds in crops inciuding rice.

As used herein, fluazifop-P-butyl is butyl (27?)-2-[4-[[5-(trifluoromethyl)-2pyridinyl]oxy]phenoxy]propanoate and possesses the following structure:

O

This compound is described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of fluazifop-P-butyl include its use as a herbicide for, e.g., post-emergence control of wild oats, volunteer cereals, and annual and perennial grass weeds in oilseed râpe, sugar beet, fodder beet, potatoes, vegetables, cotton, soya beans, pome fruit, stone fruit, bush fruit, vines, citrus fruit, pineapples, bananas, strawberries, sunflowers, alfalfa, coffee, omamentals and other broadleaf crops. Fluazifop-P-butyl can be used in combination with safeners, e.g., isoxadifen-ethyl or mefenpyr-diethyl.

As used herein, haloxyfop-P-methyl is methyl (27?)-2-[4-[[3-chloro-5-(trifluoromethyl)-2pyridinyl]oxy]phenoxy]propanoate and possesses the following structure:

O

Cl

This compound is described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of haloxyfop-P-methyl include its use as a herbicide for, e.g., post-emergence control of annual and perennial grasses in a variety of crops.

As used herein, metamifop is (27?)-2-[4-[(6-chloro-2-benzoxazolyl)oxy]phenoxy]-?/-(2fluorophenyl)-JV-methylpropanamide and possesses the following structure:

This compound is described in The Pesticide Manual, Fifteenth Edition, 2009.

Exemplary uses of metamifop include its use as a herbicide for, e.g., post-emergence control of annual and perennial grasses in a variety of crops, inciuding rice.

As used herein, pinoxaden is 8-(2,6-diethyl-4-methylphenyl)-1,2,4,5-tetrahydro-7-oxo72/-pyrazolo[l,2-<Z][l,4,5]oxadiazepin-9-yl 2,2-dimethylpropanoate and possesses the following structure:

This compound is described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of pinoxaden include its use as a herbicide for, e.g., post-emergence control of annual grasses, inciuding Alopecurus, Apera, Avena, Lolium, Phalaris and Setaria spp., in wheat and barley.

As used herein, profoxydim is 2-[l-[[2-(4-chlorophenoxy)propoxy]imino]butyl]-3hydroxy-5-(tetrahydro-2H-thiopyran-3-yl)-2-cyclohexen-l-one and possesses the following 10 structure:

This compound is described in The Pesticide Manual, Fifteenth Edition, 2009.

Exemplary uses of profoxydim include its use as a herbicide for, e.g., control of grass weeds in rice.

As used herein, quizalofop-P-ethyl is ethyl (2Æ)-2-[4-[(6-chloro-2quinoxalinyl)oxy]phenoxy]propanoate and possesses the following structure:

This compound is described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of quizalofop-P-ethyl include its use as a herbicide for, e.g., sélective postemergence control of annual and perennial grass weeds in crops.

As used herein, sethoxydim is 2-[l-(ethoxyimino)butyl]-5-[2-(ethylthio)propyl]-3hydroxy-2-cyclohexen-l-one and possesses the following structure:

This compound is described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of sethoxydim include its use as a herbicide for, e.g., control of annual and perennial grasses in broadleaf crops.

As used herein, tralkoxydim is 2-[l-(ethoxyimino)propyl]-3-hydroxy-5-(2,4,6trimethylphenyl)-2-cyclohexen-l-one and possesses the following structure:

This compound is described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of tralkoxydim include its use as a herbicide for, e.g., post-emergence control of annual grass weeds in wheat and barley.

As used herein, herbicide means a compound, e.g., active ingrédient that kills, controls or otherwise adversely modifies the growth of plants.

As used herein, a herbicidally effective or végétation controlling amount is an amount of active ingrédient which causes an adversely modifying effect to the végétation e.g., causing déviations from natural development, killing, effecting régulation, causing desiccation, causing retardation, and the like.

As used herein, controlling undesirable végétation means preventing, reducing, killing, or otherwise adversely modifying the development of plants and végétation. Described herein are methods of controlling undesirable végétation through the application of certain herbicide combinations or compositions. Methods of application include, but are not Iimited to applications to the végétation or locus thereof, e.g., application to the area adjacent to the végétation, as well as preemergence, postemergence, foliar (broadcast, directed, banded, spot, mechanical, over-the-top, or rescue), and in-water applications (emerged and submerged végétation, broadcast, spot, mechanical, water-injected, granular broadcast, granular spot, shaker bottle, or stream spray) via hand, backpack, machine, tractor, or aerial (airplane and helicopter) application methods..

As used herein, plants and végétation include, but are not limited to, germinant seeds, emerging seedlings, plants emerging from végétative propagules, immature végétation, and established végétation.

As used herein, agriculturally acceptable salts and esters refer to salts and esters that exhibit herbicidal activity, or that are or can be converted in plants, water, or soil to the referenced herbicide. Exemplary agriculturally acceptable esters are those that are or can be hydrolyzed, oxidized, metabolized, or otherwise converted, e.g., in plants, water, or soil, to the correspondîng carboxylic acid which, depending on the pH, may be in the dissociated or undissociated form.

Exemplary salts include those derived from alkali or alkaline earth metals and those derived from ammonia and amines. Exemplary cations include sodium, potassium, magnésium, and aminium cations of the formula:

R¹R²R³R⁴N⁺ wherein R¹, R², R³ and R⁴ each, independently represents hydrogen or C1-C12 alkyl, C3-C12 alkenyl or C3-C12 alkynyl, each of which is optionally substituted by one or more hydroxy, C1-C4 alkoxy, C1-C4 alkylthio or phenyl groups, provided that R¹, R², R³ and R⁴ are sterically compatible. Additionally, any two of R¹, R², R³ and R⁴ together may represent an aliphatic difunctional moiety containing one to twelve carbon atoms and up to two oxygen or sulfur atoms. Salts can be prepared by treatment with a métal hydroxide, such as sodium hydroxide, with an amine, such as ammonia, trimethylamine, diethanolamine, 2-methylthiopropylamine, bisallylamine, 2-butoxyethylamine, morpholine, cyclododecylamine, or benzylamine or with a tetraalkylammonium hydroxide, such as tétraméthylammonium hydroxide or choline hydroxide.

Exemplary esters include those derived from C1-C12 alkyl, C3-C12 alkenyl, C3-C12 alkynyl or C7-C10 aryl-substituted alkyl alcohols, such as methyl alcohol, isopropyl alcohol, 1-butanol, 2ethylhexanol, butoxyethanol, methoxypropanol, allyl alcohol, propargyl alcohol, cyclohexanol or unsubstituted or substituted benzyl alcohols. Benzyl alcohols may be substituted with from 1-3 substituents independently selected from halogen, C1-C4 alkyl or C1-C4 alkoxy. Esters can be prepared by coupling of the acids with the alcohol using any number of suitabie activating agents such as those used for peptide couplings such as dicyclohexylcarbodiimide (DCC) or carbonyl diimidazole (CDI); by reacting the acids with alkylating agents such as alkylhalides or alkylsulfonates in the presence of a base such as triethylamine or lithium carbonate; by reacting the corresponding acid chloride of an acid with an appropriate alcohol; by reacting the corresponding acid with an appropriate alcohol in the presence of an acid catalyst orby transestérification.

COMPOSITIONS AND METHODS

Provided herein are herbicidal compositions comprising a herbicidally effective amount of (a) a compound of the formula (I)

NH,

Cl

OH or an agriculturally acceptable sait or ester of thereof, and (b) an ACCase inhibitor. In certain embodiments, the ACCase inhibitor is clethodim, clodinafop-propargyl, cyhalofop-R-butyl, diclofop-methyl, fenoxaprop-P-ethyl, fluazifop-P-butyl, haloxyfop-R-methyl, metamifop, pinoxaden, profoxydim, quizalofop-P-ethyl, sethoxydim or tralkoxydim or dérivative thereof, e.g., sait, carboxylic acid, carboxylate sait, or ester thereof.

Provided herein are also methods of controlling undesirable végétation comprising contacting the végétation or the locus thereof, i.e., are adjacent to the végétation, with or applying to the soil or water to prevent the emergence or growth of végétation a herbicidally effective amount of the compound of formula (I) and (b) an ACCase inhibitor. In certain embodiments, the methods employ the compositions described herein.

Furthermore, in some embodiments, the combination of compound (I) or agriculturally acceptable sait or ester thereof and ACCase inhibitors, or an agriculturally acceptable sait or ester thereof exhibits synergism, e.g., the herbicidal active ingrédients are more effective in combination than when applied individually. Synergism has been defined as “an interaction of two or more factors such that the effect when combined is greater than the predicted effect based on the response of each factor applied separately.” Senseman, S., ed. Herbicide Handbook. 9^thed. Lawrence: Weed Science Society of America, 2007. In certain embodiments, the compositions exhibit synergy as determined by the Colby’s équation. Colby, S.R. 1967.

Calculation of the synergistic and antagonistic response of herbicide combinations. Weeds

15:20-22.

In certain embodiments of the compositions and methods described herein, the compound of formula (I), i.e., the carboxylic acid, is employed. In certain embodiments, a carboxylate sait of the compound of formula (I) is employed. In certain embodiments, an aralkyl or alkyl ester is employed. In certain embodiments, a benzyl, substituted benzyl, or Cm alkyl, e.g., n-butyl ester is employed. In certain embodiments, the benzyl ester is employed.

In some embodiments, the compound of formula (I) or sait or ester thereof and ACCase inhibitor are formulated in one composition, tank mixed, applied simultaneously, or applied sequentially.

Herbicidal activity is exhibited by the compounds when they are applied directly to the plant or to the locus of the plant at any stage of growth. The effect observed dépends upon the plant species to be controlled, the stage of growth of the plant, the application parameters of dilution and spray drop size, the particle size of solid components, the environmental conditions at the time of use, the spécifie compound employed, the spécifie adjuvants and carriers employed, the 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 sélective herbicidal action. In some embodiments, 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 undesirable végétation to achieve the maximum control of weeds.

In some embodiments, the compositions and methods 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, com/maize, sugarcane, sunflower, oilseed râpe, canola, sugar beet, soybean, cotton, pineapple, pastures, grasslands, rangelands, fallowland, turf, tree and vine orchards, aquatics, plantation crops, vegetables, industrial végétation management (IVM) and rights of way (ROW).

In certain embodiments, the compositions and methods provided herein are utilized to control weeds in rice. In certain embodiments, the rice is direct-seeded, water-seeded, or transplanted rice.

The compositions and methods described herein may be used to control undesirable végétation in glyphosate-tolerant-, 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitor-tolerant-, glufosinate-tolerant-, glutamine synthetase inhibitor-tolerant-, dicambatolerant-, phenoxy auxin-tolerant-, pyridyloxy auxin-tolerant-, auxin-tolerant-, auxin transport inhibitor-tolerant-, aryloxyphenoxypropionate-tolerant-, cyclohexanedione-tolerant-, phenylpyrazoline-tolerant-, acetyl CoA carboxylase (ACCase) inhibitor-tolerant-, imidazolinonetolerant-, sulfonylurea-tolerant-, pyrimidinylthiobenzoate-tolerant-, triazolopyrimidine-tolerant-, sulfonylaminocarbonyltriazolinone-tolerant-, triazolopyrimidine-tolerant-, sulfonylaminocarbonyltriazolinone-tolerant-, acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitor-tolerant-, 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor tolérant-, phytoene desaturase inhibitor-tolerant-, carotenoid biosynthesis inhibitor-tolerant-, protoporphyrinogen oxidase (PPO) inhibitor -tolérant-, cellulose biosynthesis inhibitor-tolerant-, mitosis inhibitor-tolerant-, microtubule inhibitor-tolerant-, very long chain fatty acid inhibitortolerant-, fatty acid and lipid biosynthesis inhibitor-tolerant-, photosystem I inhibitor-tolerant-, photosystem II inhibitor-tolerant-, triazine-tolerant- and bromoxynil-tolerant- crops (such as, but not limited to, soybean, cotton, canola/oilseed râpe, rice, cereals, corn, sorghum, sunflower, sugar beet, sugarcane, turf, etc.), for example, in conjunction with glyphosate, EPSP synthase inhibitors, glufosinate, glutamine synthase inhibitors, dicamba, phenoxy auxins, pyridyloxy auxins, synthetic auxins, auxin transport inhibitors, aryloxyphenoxypropionates, cyclohexanediones, phenylpyrazolines, ACCase inhibitors, imidazolinones, sulfonylureas, pyrimidinylthiobenzoates, dimethoxy-pyrimidines, triazolopyrimidine sulfonamides, sulfonylaminocarbonyltriazolinones, ALS or AHAS inhibitors, HPPD inhibitors, phytoene desaturase inhibitors, carotenoid biosynthesis inhibitors, PPO inhibitors, cellulose biosynthesis inhibitors, mitosis inhibitors, microtubule inhibitors, very long chain fatty acid inhibitors, fatty acid and lipid biosynthesis inhibitors, photosystem I inhibitors, photosystem II inhibitors, PPO inhibitors, triazines, and bromoxynil The compositions and methods may be used in controlling undesirable végétation in crops possessing multiple or stacked traits conferring tolérance to multiple chemistries and/or inhibitors of multiple modes of action. In some embodiments, the compound of formula (I) or sait or ester thereof and complementary herbicide or sait or ester thereof are used in combination with herbicides that are sélective for the crop being treated and which complément the spectrum of weeds controlled by these compounds at the application rate employed. In some embodiments, the compositions described herein and other complementary herbicides are applied at the same time, either as a combination formulation, tank mix or sequentially.

The compositions and methods may be used in controlling undesirable végétation in crops possessing agronomie stress tolérance (including but not limited to drought, cold, heat, sait, water, nutrient, fertility, pH), pest tolérance (including but not limited to insects, fungi and pathogens) and crop improvement traits (including but not limited to yield; protein, carbohydrate, or oil content; protein, carbohydrate, or oil composition; plant stature and plant architecture).

The compositions and methods provided herein are utilized to control undesirable végétation. Undesirable végétation includes, but is not limited to, undesirable végétation that occurs in rice, cereals, wheat, barley, oats, rye, sorghum, com/maize, sugarcane, sunflower, oilseed râpe, canola, sugar beet, soÿbean, cotton, pineapple, range and pasture, grasslands, fallowland, turf, tree and vine orchards, aquatics, plantation crops, vegetables, industrial végétation management (IVM) and rights of way (ROW).

In some embodiments, the methods provided herein are utilized to control undesirable végétation in rice. In certain embodiments, the undesirable végétation is Brachiariaplatyphylla (Groseb.) Nash or Urochloaplatyphylla (Nash) R.D. Webster (broadleaf signalgrass, BRAPP), Digitaria sanguin ali s (L.) Scop. (large crabgrass, DIGSA), Echinochloa species (ECHSS), Echinochloa crus-galli (L.) P. Beauv. (bamyardgrass, ECHCG), Echinochloa crus-pavonis (Kunth) Schult. (gulf cockspur, ECHCV), Echinochloa colonum (L.) LINK (junglerice, ECHCO), Echinochloa oryzoides (Ard.) Fritsch (early watergrass, ECHOR), Echinochloa oryzicola (Vasinger) Vasinger (late watergrass, ECHPH), Echinochloa phyllopogon (Stapf) Koso-Pol. (rice bamyardgrass, ECHPH), Echinochloapolystachya (Kunth) Hitchc. (creeping river grass, ECHPO), Ischaemum rugosum Salisb. (saramollagrass, ISCRU), Leptochloa chinensis (L.) Nees (Chinese sprangletop, LEFCH), Leptochloa fascicularis (Lam.) Gray (bearded sprangletop, LEFFA), Leptochloa panicoides (Presl.) Hitchc. (Amazon sprangletop, LEFPA), Oryza species (red and weedy rice, ORYSS), Panicum dichotomiflorum (L.) Michx. (fall panicum, PANDI), Paspalum dilatatum Poir. (dallisgrass, PASDI), Rottboellia cochinchinensis (Lour.) W.D. Clayton (itchgrass, ROOEX), Cyperus species (CYPSS), Cyperus difformis L. (smallflower flatsedge, CYPDI), Cyperus dubius Rottb. (MAPDU), Cyperus esculentus L. (yellow nutsedge, CYPES), Cyperus iria L. (rice flatsedge, CYPIR), Cyperus rotundus L. (purple nutsedge, CYPRO), Cyperus serotinus ROTTB./C.B.Claike (CYPSE), Eleocharis species (ELOSS), Fimbristylis miliacea (L.) Vahl (globe fringerush, FIMMI), Schoenoplectus species (SCPSS), Schoenoplectus juncoides Roxb. (Japanese bulrush, SCPJU), Bolboschoenus maritimus (L.) Palla or Schoenoplectus maritimus L. Lye (sea clubrush, SCPMA), Schoenoplectus mucronatus L. (ricefield bulrush, SCPMU), Aeschynomene species, (jointvetch, AESSS), Altemanthera philoxeroides (Mart.) Griseb. (alligatorweed, ALRPH), Alismaplantago-aquatica L. (common waterplantain, ALSPA), Amaranthus species, (pigweeds and amaranths, AMASS), Ammannia coccinea Rottb. (redstem, AMMCO), Commelina benghalensïs L. (Benghal dayflower, COMBE), Eclipta alba (L.) Hassk. (American false daisy, ECLAL), Heteranthera limosa (SW.) Willd./Vahl (ducksalad, HETLI), Heteranthera reniformis R. & P. (roundleaf mudplantain, HETRE), Ipomoea species (momingglories, IPOSS), Ipomoea hederacea (L.) Jacq. (ivyleaf momingglory, IPOHE), Lindemia dubia (L.) Pennell (low false pimpemel, LIDDU), Ludwigia species (LUDSS), Ludwigia linifolia Poir. (southeastem primrose-willow, LUDLI), Ludwigia octovalvis (Jacq.) Raven (longfruited primrose-willow, LUDOC), Monochoria korsakowii Regel & Maack (monochoria, MOOKA), Monochoria vaginalis (Burm. F.) C. Presl ex Kuhth, (monochoria, MOOVA), Murdannia nudiflora (L.) Brenan (doveweed, MUDNU), Polygonum pensylvanicum L., (Pennsylvania smartweed, POLPY), Polygonum persicaria L. (ladysthumb, POLPE), Polygonum hydropiperoides Michx. (POLHP, mild smartweed), Rotala indica (Willd.) Koehne (Indian toothcup, ROTIN), Sagittaria species, (arrowhead, SAGSS), Sesbania exaltata (Raf.) Cory/Rydb. Ex Hill (hemp sesbania, SEBEX), or Sphenoclea zeylanica Gaertn. (gooseweed, SPDZE).

In some embodiments, the methods provided herein are utilized to control undesirable végétation in cereals. In certain embodiments, the undesirable végétation is Alopecurus myosuroides Huds. (blackgrass, ALOMY), Apera spica-venti (L.) Beauv. (windgrass, APESV), Avena fatua L. (wild oat, AVEFA), Bromus tectorum L. (downy brome, BROTE), Lolium multiflorum Lam. (Italian ryegrass, LOLMU), Phalaris minor Retz, (littleseed canarygrass, PHAMI), Poa annua L. (annual bluegrass, POANN), Setaria pumila (Poir.) Roemer & J.A. Schultes (yellow foxtail, SETLU), Setaria viridis (L.) Beauv. (green foxtail, SETVI), Amaranthus retroflexus L. (redroot pigweed, AMARE), Brassica species (BRSSS), Chenopodium album L. (common lambsquarters, CHEAL), Cirsium arvense (L.) Scop. (Canada thistle, CIRAR), Galium aparine L. (catchweed bedstraw, GALAP), Kochia scoparia (L.) Schrad. (kochia, KCHSC), Lamium purpureum L. (purple deadnettle, LAMPU), Matricaria recutita L. (wild chamomile, MATCH), Matricaria matricarioides (Less.) Porter (pineappleweed, MATMT), Papaver rhoeas L. (common poppy, PAPRH), Polygonum convolvulus L. (wild buckwheat, POLCO), Salsola tragus L. (Russian thistle, SASKR), Sinapis species (SINSS), Sinapis arvensis L. (wild mustard, SINAR) Stellaria media (L.) Vill. (common chickweed, STEME), Veronica persica Poir. (Persian speedwell, VERPE), Viola arvensis Murr. (field violet, VIOAR), or Viola tricolor L. (wild violet, VIOTR).

In some embodiments, the methods provided herein are utilized to control undesirable végétation in range and pasture, fallowland, IVM and ROW. In certain embodiments, the undesirable végétation is Ambrosia artemisiifolia L. (common ragweed, AMBEL), Cassia obtusifolia (sickle pod, CASOB), Centaurea maculosa auct. non Lam. (spotted knapweed, CENMA), Cirsium arvense (L.) Scop. (Canada thistle, CIRAR), Convolvulus arvensis L. (field bindweed, CONAR), Daucus carota L. (wild canot, DAUCA), Euphorbia esula L. (leafy spurge, EPHES), Lactuca serriola L./Tom. (prickly lettuce, LACSE), Plantago lanceolata L. (buckhom plantain, PLALA), Rumex obtusifolius L. (broadleaf dock, RUMOB), Sida spinosa L. (prickly sida, SIDSP), Sinapis arvensis L. (wild mustard, SINAR), Sonchus arvensis L. (perennial sowthistle, SONAR), Solidago species (goldenrod, SOOSS), Taraxacum officinale G.H. Weber ex Wiggers (dandelion, TAROF), Trifolium repens L. (white clover, TRFRE), or Urtica dioica L. (common nettle, URTDI).

In some embodiments, the methods provided herein are utilized to control undesirable végétation found in row crops, tree and vine crops and perennial crops. In certain embodiments, the undesirable végétation is Alopecurus myosuroides Huds. (blackgrass, ALOMY), Avena fatua L. (wild oat, AVEFA), Brachiaria decumbens Stapf. or Urochloa decumbens (Stapf) R.D. Webster (Surinam grass, BRADC), Brachiaria brizantha (Hochst. ex A. Rich.) Stapf. or Urochloa brizantha (Hochst. ex A. Rich.) R.D. (beard grass, BRABR), Brachiaria platyphylla (Groseb.) Nash or Urochloa platyphylla (Nash) R.D. Webster (broadleaf signalgrass, BRAPP), Brachiaria plantaginea (Link) Hitchc. or Urochloaplantaginea (Link) R.D. Webster (alexandergrass, BRAPL), Cenchrus echinatus L. (southem sandbur, CENEC), Digitaria horizontalis Willd. (Jamaican crabgrass, DIGHO), Digitaria insularis (L.) Mez ex Ekman (sourgrass, TRCIN), Digitaria sanguinalis (L.) Scop. (large crabgrass, DIGSA), Echinochloa crus-galli (L.) P. Beauv. (bamyardgrass, ECHCG), Echinochloa colonum (L.) Link (junglerice, ECHCO), Eleusine indica (L.) Gaertn. (goosegrass, ELEIN), Lolium multiflorum Lam. (Italian iyegrass, LOLMU), Panicum dichotomiflorum Michx. (fall panicum, PANDI), Panicum miliaceum L. (wild-proso millet, PANMI), Setaria faberi Herrm. (giant foxtail, SETFA), Setaria viridis (L.) Beauv. (green foxtail, SETVI), Sorghum halepense (L.) Pers. (Johnsongrass, SORHA), Sorghum bicolor (L.) Moench ssp. Arundinaceum (shattercane, SORVU), Cyperus esculentus L. (yellow nutsedge, CYPES), Cyperus rotundus L. (purple nutsedge, CYPRO), Abutilon theophrasti Medik. (velvetleaf, ABUTH), Amaranthus species (pigweeds and amaranths, AMAS S), Ambrosia artemisiifolia L. (common ragweed, AMBEL), Ambrosia psilostachya DC. (western ragweed, AMBPS), Ambrosia trifida L. (giant ragweed, AMBTR), Anoda cristata (L.) Schlecht. (spurred anoda, ANVCR), Asclepias syriaca L. (common milkweed, ASCSY), Bidenspilosa L. (haiiy beggarticks, BIDPI), Borreria species (BOISS), Borreria alata (Aubl.) DC. or Spermacoce alata Aubl. (broadleaf buttonweed, BOILF), Spermacose latifolia (broadleaved button weed, BOILF), Chenopodium album L. (common lambsquarters, CHEAL), Cirsium arvense (L.) Scop. (Canada thistle, CIRAR), Commelina benghalensis L. (tropical spiderwort, COMBE), Datura stramonium L. (jimsonweed, DATST), Daucus carota L. (wild carrot, DAUCA), Euphorbia heterophylla L. (wild poinsettia, EPHHL), Euphorbia hirta L. or Chamaesyce hirta (L.) Millsp. (garden spurge, EPHHI), Euphorbia dentata Michx. (toothed spurge, EPHDE), Erigeron bonariensis L. or Conyza bonariensis (L.) Cronq. (hairy fleabane, ERIBO), Erigeron canadensis L. or Conyza canadensis (L.) Cronq. (Canadien fleabane, ERICA), Conyza sumatrensis (Retz.) E. H. Walker (tall fleabane, ERIFL), Helianthus annuus L. (common sunflower, HELAN), Jacquemontia tamnifolia (L.) Griseb. (smallflower momingglory, IAQTA), Ipomoea hederacea (L.) Jacq. (ivyleaf momingglory, IPOHE), Ipomoea lacunosa L. (white momingglory, IPOLA), Lactuca serriola L./Tom. (prickly lettuce, LACSE), Portulaca oleracea L. (common purslane, POROL), Richardia species (pusley, RCHSS), Sida species (sida, SIDSS), Sida spinosa L. (prickly sida, SIDSP), Sinapis arvensis L. (wild mustard, SINAR), Solanum ptychanthum Dunal (eastem black nightshade, SOLPT), Tridax procumbens L. (coat buttons, TRQPR), Tridax procumbens L. (coat buttons, TRQPR), or Xanthium strumarium L. (common cocklebur, XANST).

In some embodiments, the methods provided herein are utilized to control undesirable végétation in turf. In certain embodiments, the undesirable végétation is Bellis perennis L. (English daisy, BELPE), Cyperus esculentus L. (yellow nutsedge, CYPES), Cyperus species (CYPSS), Digitaria sanguinalis (L.) Scop. (large crabgrass, DIGSA), Diodia virginiana L. (Virginia buttonweed, DIQVI), Euphorbia species (spurge, EPHSS), Glechoma hederacea L. (ground ivy, GLEHE), Hydrocotyle umbellata L. (dollarweed, HYDUM), Kyllinga species (kyllinga, KYLSS), Lamium amplexicaule L. (henbit, LAMAM), Murdannia nudiflora (L.) Brenan (doveweed, MUDNU), Oxalis species (woodsorrel, OXASS), Plantago major L. (broadleaf plantain, PLAMA), Plantago lanceolata L. (buckhom/narrowleaf plantain, PLALA), Phyllanthus urinaria L. (chamberbitter, PYLTE), Rumex obtusifolius L. (broadleaf dock, RUMOB), Stachys floridana Shuttlew. (Florida betony, STAFL), Stellaria media (L.) Vill. (common chickweed, STEME), Taraxacum officinale G.H. Weber ex Wiggers (dandelion, TAROF), Trifolium repens L. (white clover, TRFRE), or Viola species (wild violet, VIOSS).

In some embodiments, the compositions and methods provided herein are utilized to control undesirable végétation consisting of grass, broadleaf and sedge weeds. In certain embodiments, the compositions and methods provided herein are utilized to control undesirable végétation including Avena, Brachiaria, Cyperus, Digitaria, Echinochloa, Fimbristylis,

Ipomoea, Ischaemum, Leptochloa, Lolium, Schoenoplectus and Sesbania.

In some embodiments, the combination of compound (I) or agriculturally acceptable ester or sait thereof and ACCase inhibitors or agriculturally acceptable sait or ester thereof is used to control Avena fatua L.(wild oat, AVEFA), Brachiaria platyphylla (Griseb.) Nash (broadleaf signalgrass, BRAPP), Cyperus difformis L. (smallflower umbrella sedge, CYPDI), Cyperus esculentus L. (yellow nutsedge, CYPES), Cyperus iria L. (rice flatsedge, CYPIR), Cyperus rotundus L. (purple nutsedge, CYPRO), Digitaria sanguinalis (L.) Scop. (large crabgrass, DIGSA), Echinochloa crus-galli (L.) Beauv. (bamyardgrass, ECHCG), Echinochloa colona (L.) Link (junglerice, ECHCO), Fimbristylis miliacea (L.) Vahl (globe fringerush, FIMMI), Ipomoea hederacea Jacq. (ivyleaf momingglory, IPOHE), Ischaemum rugosum Salisb. (saramollagrass, ISCRU), Leptochloa chinensis (L.) Nees (Chinese sprangletop, LEFCH), Lolium multiflorum Lam. (Italian ryegrass, LOLMU), Schoenoplectus juncoides (Roxb.) Palla (Japanese bulrush, SCPJU), Schoenoplectus maritimus (L.) Lye (sea clubrush, SCPMA), Schoenoplectus mucronatus (ricefield bulrush, SCPMU) and Sesbania exaltata (hemp sesbania, SEBEX).

The compounds of formula I or agriculturally acceptable sait or ester thereof may be used to control herbicide résistant or tolérant weeds. The methods employing the combination of a compound of formula I or agriculturally acceptable sait or ester thereof and the compositions described herein may also be employed to control herbicide résistant or tolérant weeds. Exemplary résistant or tolérant weeds include, but are not limited to, biotypes résistant or tolérant to acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors, (e.g., imidazolinones, sulfonylureas, pyrimidinylthiobenzoates, triazolopyrimidines, sulfonylaminocarbonyltriazolinones), photosystem II inhibitors (e.g., phenylcarbamates, pyridazinones, triazines, triazinones, uracils, amides, ureas, benzothiadiazinones, nitriles, phenylpyridazines), acetyl CoA carboxylase (ACCase) inhibitors (e.g·, aryloxyphenoxypropionates, cyclohexanediones, phenylpyrazolines), synthetic auxins, (e.g., benzoic acids, phenoxycarboxylic acids, pyridine carboxylic acids, quinoline carboxylic acids), auxin transport inhibitors (e.g., phthalamates, semicarbazones), photosystem I inhibitors, (e.g., bipyridyliums), 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, (e.g., glyphosate), glutamine synthetase inhibitors (e.g., glufosinate, bialafos), microtubule assembly inhibitors, (e.g., benzamides, benzoic acids, dinitroanilines, phosphoramidates, pyridines), mitosis inhibitors (e.g., carbamates), very long chain fatty acid (VLCFA) inhibitors (e.g., acetamides, chloroacetamides, oxyacetamides, tetrazolinones), fatty acid and lipid synthesis inhibitors, (e.g., phosphorodithioates, thiocarbamates, benzofuranes, chlorocarbonic acids), protoporphyrinogen oxidase (PPO) inhibitors (e.g., diphenylethers, N-phenylphthalimides, oxadiazoles, oxazolidinediones, phenylpyrazoles, pyrimidindiones, thiadiazoles, triazolinones), carotenoid biosynthesis inhibitors,, phytoene desaturase (PDS) inhibitors (e.g., amides, anilidex, furanones, phenoxybutan-amides, pyridiazinones, pyridines), 4-hydroxyphenyl-pyruvatedioxygenase (HPPD) inhibitors, (e.g., callistemones, isoxazoles, pyrazoles, triketones), cellulose biosynthesis inhibitors (e.g., nitriles, benzamides, quinclorac, triazolocarboxamides), mitosis inhibitors, cellulose biosynthesis inhibitors, herbicides with multiple modes-of-action such as quinclorac, and unclassified herbicides such as arylaminopropionic acids, difenzoquat, endothall, and organoarsenicals. Exemplary résistant or tolérant weeds include, but are not limited to, biotypes with résistance or tolérance to multiple herbicides, biotypes with résistance or tolérance to multiple chemical classes, biotypes with résistance or tolérance to multiple herbicide modesof-action and biotypes with multiple résistance or tolérance mechanisms (e.g., target site résistance or metabolic résistance).

In some embodiments, an agriculturally acceptable ester or sait of compound (I) is employed. In certain embodiments, an agriculturally acceptable ester is employed. In certain embodiments, the ester is a Cm alkyl ester. In certain embodiments, the ester is an n-butyl ester. In certain embodiments, the ester is a benzyl ester. In certain embodiments, compound (I), which is a carboxylic acid, is employed.

In certain embodiments of the compositions and methods described herein, the compound of formula (I) or sait or ester thereof is used in combination with clethodim or sait or ester thereof. With respect to the compositions, in some embodiments, the weight ratio ofthe compound of formula (I) or sait or ester thereof to clethodim or sait or ester thereof is within the range of from about 1:140 to about 9:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to clethodim or sait or ester thereof is within the range of from about 1:48 to about 3:1. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl or n-butyl ester and clethodim. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 20 grams active ingrédient per hectare (gai/ha) to about 580 gai/ha based on the total amount of active ingrédients in the composition. In certain embodiments, the composition is applied at an application rate of from about 20 grams active ingrédient per hectare (gai/ha) to about 260 gai/ha based on the total amount of active ingrédients in the composition. In some embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation with a compound of formula (I) or sait or ester thereof and clethodim or sait thereof,

e.g., sequentially or simultaneously. In some embodiments, the clethodim or sait thereof is applied at a rate from about 17.5 gai/ha to about 280 gai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the clethodim or sait thereof is applied at a rate from about 70 gai/ha to about 280 gai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 8 gae/ha to about 32 gae/ha. In certain embodiments, the methods utilize the compound of formula (I), or its benzyl or n-butyl ester and clethodim for the control of BRAPP, DIGSA, CYPES and SCPJU.

In certain embodiments of the compositions and methods described herein, the compound of formula (I) or sait or ester thereof is used in combination with clodinafop-propargyl or sait, carboxylate sait, carboxylic acid, or ester thereof. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to clodinafop-propargyl or sait, carboxylate sait, carboxylic acid, or ester thereof is within the range of from about 1:40 to about 60:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to clodinafop-propargyl or sait, carboxylate sait, carboxylic acid, or ester thereof is within the range of from 1:36 to about 10:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to clodinafop-propargyl or sait, carboxylate sait, carboxylic acid, or ester thereof is within the range of from 1:6 to about 1:1.5. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl or n-butyl ester and clodinafop-propargyl. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 7 grams active ingrédient per hectare (gai/ha) to about 380 gai/ha based on the total amount of active ingrédients in the composition. In certain embodiments, the composition is applied at an application rate of from about 20 grams active ingrédient per hectare (gai/ha) to about 40 gai/ha based on the total amount of active ingrédients in the composition. In some embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation with a compound of formula (I) or sait or ester thereof and clodinafop-propargyl or sait, carboxylate sait, carboxylic acid, or ester thereof, e.g., sequentially or simultaneously. In some embodiments, the clodinafop-propargyl or sait, carboxylate sait, carboxylic acid, or ester thereof is applied at a rate from about 5 gai/ha to about 80 gai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the clodinafop-propargyl or sait, carboxylate sait, carboxylic acid, or ester thereof is appiied at a rate from about 15 gai/ha to about 30 gai/ha and the compound of formula (I) of sait or ester thereof is appiied at a rate from about 5 gae/ha to about 10 gae/ha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and clodinafoppropargyl are used to control LOLMU, KCHSC, PHAMI, APESV and ALOMY.

In certain embodiments of the compositions and methods described herein, the compound of formula (I) or sait or ester thereof is used in combination with cyhalofop-R-butyl or carboxylic acid, carboxylate sait, or ester thereof. With respect to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to cyhalofop-R-butyl carboxylic acid, carboxylate sait, or ester thereof is within the range of from about 1:155 to about 6:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to cyhalofop-R-butyl or carboxylic acid, carboxylate sait, or ester thereof is within the range of from 1:32 to about 1:4. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to cyhalofop-R-butyl or carboxylic acid, carboxylate sait, or ester thereof is within the range of from about 1:42 to about 10:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to cyhalofop-R-butyl or carboxylic acid, carboxylate sait, or ester thereof is within the range of from about 1:21 to about 5:1. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl ester and cyhalofop-R-butyl. In one embodiment, the composition comprises the compound of formula (I) and cyhalofop-R-butyl, wherein the weight ratio of the compound of formula (I) to cyhalofop-R-butyl is about 1:20.6 to about 1:2.5. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and cyhalofop-R-butyl, wherein the weight ratio of the benzyl ester of the compound of formula (I) to cyhalofop-R-butyl is about 1:23 to about 5:1. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation a composition described herein. In some embodiments, the composition is appiied at an application rate of from about 52 grams active ingrédient per hectare (gai/ha) to about 610 gai/ha based on the total amount of active ingrédients in the composition. In certain embodiments, the composition is appiied at an application rate of from about 99 grams active ingrédient per hectare (gai/ha) to about 320 gai/ha based on the total amount of active ingrédients in the composition. In some embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation with a compound of formula (I) or sait or ester thereof and cyhalofop-R-butyl or carboxylic acid, carboxylate sait, or ester thereof, e.g., sequentially or simultaneously. In some embodiments, the cyhalofop-R-butyl or sait or ester thereof is applied at a rate from about 50 gai/ha to about 310 gai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the cyhalofop-R-butyl or carboxylic acid, carboxylate sait, or ester thereof is applied at a rate from about 45 gai/ha to about 600 gai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 4 g acid équivalent per hectare (gae/ha) to about 85 gae/ha. In some embodiments, the cyhalofop-R-butyl or carboxylic acid, carboxylate sait, or ester thereof is applied at a rate from about 90 gai/ha to about 300 gai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 8 g acid équivalent per hectare (gae/ha) to about 42 gae/ha. In certain embodiments, the methods utilize the compound of formula (I), or its benzyl ester and cyhalofop-R-butyl. In one embodiment, the methods utilize the compound of formula (I) and cyhalofop-R-butyl, wherein the compound of formula (I) is applied at a rate of from about 8.75 g acid équivalent per hectare (gae/ha) to about 42.4 gae/ha, and cyhalofop-R-butyl is applied at a rate of about 90 gai/ha to about 280 gai/ha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and cyhalofop-R-butyl, wherein the benzyl ester of the compound of formula (I) is applied at a rate of from about 8.75 g acid équivalent per hectare (gae/ha) to about 35 gae/ha, and cyhalofop-R-butyl is applied at a rate of about 90 gai/ha to about 300 gai/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or sait or ester thereof in combination with cyhalofop-R-butyl or carboxylic acid, carboxylate sait, or ester thereof are used to controi ISCRU, IPOHE, ECHOR, SCPSU, LEFCH, SCPMA, CYPIR, FIMMI, SEBEX, CYPDI, ECHCG, ECHSS, or SCPMU.

In certain embodiments of the compositions and methods described herein, the compound of formula (I) or sait or ester thereof is used in combination with diclofop-methyl or carboxylic acid, carboxylate sait, or ester thereof. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to diclofop-methyl or carboxylic acid, carboxylate sait, or ester thereof is within the range of from about 1:560 to about 5:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to diclofop-methyl or carboxylic acid, carboxylate sait, or ester thereof is within the range of from 1:255 to about 1:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to diclofop-methyl or carboxylic acid, carboxylate sait, or ester thereof is within the range of from 1:140 to about 1:9 . In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl or n-butyl ester and diclofop-methyl. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 72 grams active ingrédient per hectare (gai/ha) to about 1,420 gai/ha based on the total amount of active ingrédients in the composition. In certain embodiments, the composition is applied at an application rate of from about 73 grams active ingrédient per hectare (gai/ha) to about 610 gai/ha based on the total amount of active ingrédients in the composition. In some embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation with a compound of formula (I) or sait or ester thereof and diclofop-methyl or sait or ester thereof, e.g., sequentially or simultaneously. In some embodiments, the diclofop-methyl or sait or ester thereof is applied at a rate from about 70 gai/ha to about 1,120 gai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In certain embodiments, the methods utilize the compound of formula (I), or its benzyl or π-butyl ester and diclofop-methyl are used to control APESV, CYPIR, KCHSC and PHAMI.

In certain embodiments of the compositions and methods described herein, the compound of formula (I) or sait or ester thereof is used in combination with fenoxaprop-P-ethyl or carboxylic acid or carboxylate sait thereof or other ester, and fenoxaprop-P-ethyl can be applied alone or in combination with the safeners isoxadifen-ethyl or mefenpyr-diethyl. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to fenoxaprop-P-ethyl or carboxylic acid or carboxylate sait thereof or other ester is within the range of from about 1:170 to about 30:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to fenoxaprop-P-ethyl or carboxylic acid or carboxylate sait thereof or other ester is within the range of from 1:16 to about 1.5:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to fenoxaprop-P-ethyl or carboxylic acid or carboxylate sait thereof or other ester is within the range of from 1:16 to about 3:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to fenoxaprop-P-ethyl or carboxylic acid or carboxylate sait thereof or other ester is within the range of from about 1:32 to about 4:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to fenoxaprop-P-ethyl or carboxylic acid or carboxylate sait thereof or other ester is within the range of from about 1:16 to about 2:1. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl ester and fenoxaprop-P-ethyl. In one embodiment, the composition comprises the compound of formula (I) and fenoxaprop-P-ethyl, wherein the weight ratio of the compound of formula (I) to fenoxaprop-P-ethyl is about 1:14 to about 2:1. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and fenoxaprop-P-ethyl, wherein the weight ratio of the benzyl ester of the compound of formula (I) to fenoxaprop-P-ethyl is about 1:16 to about 1:1. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 13 grams active ingrédient per hectare (gai/ha) to about 440 gai/ha based on the total amount of active ingrédients in the composition. In certain embodiments, the composition is applied at an application rate of from about 15 grams active ingrédient per hectare (gai/ha) to about 90 gai/ha based on the total amount of active ingrédients in the composition. In some embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation with a compound of formula (I) or sait or ester thereof and fenoxaprop-P-ethyl or sait or ester thereof, e.g., sequentially or simultaneously. In some embodiments, the fenoxaprop-P-ethyl or carboxylic acid or carboxylate sait thereof or other ester is applied at a rate from about 11 gai/ha to about 140 gai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the fenoxaprop-P-ethyl or carboxylic acid or carboxylate sait thereof or other ester is applied at a rate from about 5 gai/ha to about 300 gai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 g acid équivalent per hectare (gae/ha) to about 90 gae/ha. In some embodiments, the fenoxaprop-P-ethyl or carboxylic acid or carboxylate sait thereof or other ester is applied at a rate from about 11.5 gai/ha to about 140 gai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 4.38 g acid équivalent per hectare (gae/ha) to about 42.4 gae/ha. In certain embodiments, the methods utilize the compound of formula (I), or its benzyl ester and fenoxaprop-P-ethyl. In one embodiment, the methods utilize the compound offormula (I) and fenoxaprop-P-ethyl, wherein the compound of formula (I) is applied at a rate of from about 4.38 g acid équivalent per hectare (gae/ha) to about 42.4 gae/ha, and fenoxaprop-P-ethyl is applied at a rate of about 11.5 gai/ha to about 140 gai/ha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and fenoxaprop-P-ethyl, wherein the benzyl ester of the compound of formula (I) is applied at a rate of from about 4.38 g acid équivalent per hectare (gae/ha) to about 35 gae/ha, and fenoxaprop-P-ethyl is applied at a rate of about 17.5 gai/ha to about 70 gai/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or sait or ester thereof in combination with fenoxaprop-P-ethyl or carboxylic acid or carboxylate sait thereof or other ester are used to control CYPIR, ECHOR, FIMMI, SCPJU, CYPES, KCHSC, PHAMI and APESV.

In certain embodiments of the compositions and methods described herein, the compound of formula (I) or sait or ester thereof is used in combination with fluazifop-P-butyl or carboxylic acid or carboxylate sait thereof or other ester. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to fluazifop-P-butyl or carboxylic acid or carboxylate sait thereof or other ester is within the range of from about 1:210 to about 3:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to fluazifop-P-butyl or carboxylic acid or carboxylate sait thereof or other ester is within the range of from 1:41 to about 2.5:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to fluazifop-P-butyl or carboxylic acid or carboxylate sait thereof or other ester is within the range of from 1:41 to about 1:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to fluazifop-P-butyl or sait or ester thereof is within the range of from about 1:80 to about 1:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to fluazifop-P-butyl or sait or ester thereof is within the range of from about 1:36 to about 1:2.5. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl ester and fluazifop-P-butyl. In one embodiment, the composition comprises the compound of formula (I) and fluazifop-P-butyl, wherein the weight ratio of the compound of formula (I) to fluazifop-P-butyl is about 1:36 to about 1:2.5. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and fluazifop-Pbutyl, wherein the weight ratio of the benzyl ester of the compound of formula (I) to fluazifop-Pbutyl is about 1:36 to about 1:5.1. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 47 grams active ingrédient per hectare (gai/ha) to about 720 gai/ha based on the total amount of active ingrédients in the composition. In certain embodiments, the composition is applied at an application rate of from about 50 grams active ingrédient per hectare (gai/ha) to about 200 gai/ha based on the total amount of active ingrédients in the composition. In some embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation with a compound of formula (I) or sait or ester thereof and fluazifop-P-butyl or sait or ester thereof, e.g., sequentialiy or slmultaneously. In some embodiments, the fluazifop-P-butyl or carboxylic acid or carboxylate sait thereof or other ester is applied at a rate from about 45 gae/ha to about 420 gae/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the fluazifop-P-butyl or carboxylic acid or carboxylate sait thereof or other ester is applied at a rate from about 20 gai/ha to about 400 gai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 g acid équivalent per hectare (gae/ha) to about 70 gae/ha. In some embodiments, the fluazifop-P-butyl or carboxylic acid or carboxylate sait thereof or other ester is applied at a rate from about 45 gai/ha to about 180 gai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 4.38 g acid équivalent per hectare (gae/ha) to about 35 gae/ha. In certain embodiments, the methods utilize the compound of formula (I), or its benzyl ester and fluazifop-P-butyl. In one embodiment, the methods utilize the compound of formula (I) and fluazifop-P-butyl, wherein the compound of formula (I) is applied at a rate of from about 4.38g acid équivalent per hectare (gae/ha) to about 35 gae/ha, and fluazifop-P-butyl is applied at a rate of about 45 gai/ha to about 180 gai/ha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and fluazifop-P-butyl, wherein the benzyl ester of the compound of formula (I) is applied at a rate of from about 4.38 g acid équivalent per hectare (gae/ha) to about 8.75 gae/ha, and fluazifop-P-butyl is applied at a rate of about 45 gai/ha to about 180 gai/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or sait or ester thereof in combination with fluazifop-P-butyl or carboxylic acid or carboxylate sait thereof or other ester are used to control IPOHE, ECHOR, or CYPRO.

In certain embodiments of the compositions and methods described herein, the compound of formula (I) or sait or ester thereof is used in combination with haloxyfop-R-methyl or carboxylic acid or carboxylate sait thereof or other ester. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to haloxyfop-R-methyl or carboxylic acid or carboxylate sait thereof or other ester is within the range of from about 1:45 to about 10:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to haloxyfop-R-methyl or carboxylic acid or carboxylate sait thereof or other ester is within the range of from 1:6 to about 2.5:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to haloxyfop-R-methyl or carboxylic acid or carboxylate sait thereof or other ester is within the range of from about 1:15 to about 6:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to haloxyfop-R-methyl or carboxylic acid or carboxylate sait thereof or other ester is within the range of from about 1:7 to about 2.6:1. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl ester and haloxyfop-R-methyl. In one embodiment, the composition comprises the compound of formula (I) and haloxyfop-R-methyl, wherein the weight ratio of the compound of formula (I) to haloxyfop-R-methyl is about 1:6.2 to about 2.6:1. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and haloxyfop-R-methyl, wherein the weight ratio of the benzyl ester of the compound of formula (I) to haloxyfop-Rmethyl is about 1:7 to about 1.3:1. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 32 grams active ingrédient per hectare (gai/ha) to about 420 gai/ha based on the total amount of active ingrédients in the composition. In certain embodiments, the composition is applied at an application rate of from about 10 grams active ingrédient per hectare (gai/ha) to about 60 gai/ha based on the total amount of active ingrédients in the composition. In some embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation with a compound of formula (I) or sait or ester thereof and haloxyfop-R-methyl or carboxylic acid or carboxyiate sait thereof or other ester, e.g., sequentially or simultaneously. In some embodiments, the haloxyfop-R-methyl or carboxylic acid or carboxyiate sait thereof or other ester is applied at a rate from about 6.75 gae/ha to about 120 gae/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the haloxyfop-R-methyl or carboxylic acid or carboxyiate sait thereof or other ester is applied at a rate from about 3 gai/ha to about 140 gai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 g acid équivalent per hectare (gae/ha) to about 45 gae/ha. In some embodiments, the haloxyfop-R-methyl or carboxylic acid or carboxyiate sait thereof or other ester is applied at a rate from about 6.75 gai/ha to about 70 gai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 4.38 g acid équivalent per hectare (gae/ha) to about 17.5 gae/ha. In certain embodiments, the methods utilize the compound of formula (I), or its benzyl or n-butyl ester and haloxyfop-R-methyl. In one embodiment, the methods utilize the compound of formula (I) and haloxyfop-R-methyl, wherein the compound of formula (I) is applied at a rate of from about 4.38 g acid équivalent per hectare (gae/ha) to about 35 gae/ha, and haloxyfop-Rmethyl is applied at a rate of about 6.75 gai/ha to about 70 gai/ha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and haloxyfop-R-methyl, wherein the benzyl ester of the compound of formula (I) is applied at a rate of from about 4.38 g acid équivalent per hectare (gae/ha) to about 17.5 gae/ha, and haloxyfop-R-methyl is applied at a rate of about 6.75 gai/ha to about 27 gai/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or sait or ester thereof in combination with haloxyfop-R-methyl or carboxylic acid or carboxylate sait thereof or other ester are used to control ECHCO, IPOHE, SCPJU, BRAPP, or CYPRO.

In certain embodiments of the compositions and methods described herein, the compound of formula (I) or sait or ester thereof is used in combination with metamifop or sait or ester thereof. With regard to the compositions, in some embodiments, the weight ratio ofthe compound of formula (I) or sait or ester thereof to metamifop or sait or ester thereof is within the range of from about 1:150 to about 6:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to metamifop or sait or ester thereof is within the range of from 1:34 to about 10:1. In certain embodiments, the weight ratio ofthe compound of formula (I) or sait or ester thereof to metamifop or sait or ester thereof is within the range of from 1:34 to about 1:2. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to metamifop or sait or ester thereof is within the range of from about 1:60 to about 1:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to metamifop or sait or ester thereof is within the range of from about 1:30 to about 1:2.1. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl ester and metamifop. In one embodiment, the composition comprises the compound of formula (I) and metamifop, wherein the weight ratio ofthe compound of formula (I) to metamifop is about 1:30 to about 1:2.1. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and metamifop, wherein the weight ratio of the benzyl ester of the compound of formula (I) to metamifop is about 1:30 to about 1:15. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 52 grams active ingrédient per hectare (gai/ha) to about 600 gai/ha based on the total amount of active ingrédients in the composition. In certain embodiments, the composition is applied at an application rate of from about 40 grams active ingrédient per hectare (gai/ha) to about 170 gai/ha based on the total amount of active ingrédients in the composition. In some embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation with a compound of formula (I) or sait or ester thereof and metamifop or sait or ester thereof, e.g., sequentially or simultaneously. In some embodiments, the metamifop or sait or ester thereof is applied at a rate from about 50 gai/ha to about 300 gai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the metamifop or sait or ester thereof is applied at a rate from about 30 gai/ha to about 300 gai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 g acid équivalent per hectare (gae/ha) to about 70 gae/ha. In some embodiments, the metamifop or sait or ester thereof is applied at a rate from about 75 gai/ha to about 150 gai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 4.38 g acid équivalent per hectare (gae/ha) to about 35 gae/ha. In certain embodiments, the methods utilize the compound of formula (I), or its benzyl ester and metamifop. In one embodiment, the methods utilize the compound of formula (I) and metamifop, wherein the compound of formula (I) is applied at a rate of from about 4.38 g acid équivalent per hectare (gae/ha) to about 35 gae/ha, and metamifop is applied at a rate of about 75 gai/ha to about 150 gai/ha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and metamifop, wherein the benzyl ester of the compound of formula (I) is applied at a rate of about 4.38 g acid équivalent per hectare (gae/ha), and metamifop is applied at a rate of about 75 gai/ha to about 150 gai/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or sait or ester thereof in combination with metamifop or sait or ester thereof are used to control IPOHE, ECHCG, ECHOR, IPOHE, FIMMI, SCPMA, or SCPJU.

In certain embodiments of the compositions and methods described herein, the compound of formula (I) or sait or ester thereof is used in combination with pinoxaden or sait or ester thereof. With regard to the compositions, in some embodiments, the weight ratio ofthe compound of formula (I) or sait or ester thereof to pinoxaden or sait or ester thereof is within the range of from about 1:3 0 to about 150:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to pinoxaden or sait or ester thereof is within the range of from 1:27 to about 25:1.. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to pinoxaden or sait or ester thereof is within the range of from 1:12 to about 2:1. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and pinoxaden. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 4 grams active ingrédient per hectare (gai/ha) to about 360 gai/ha based on the total amount of active ingrédients in the composition. In certain embodiments, the composition is applied at an application rate of from about 8 grams active ingrédient per hectare (gai/ha) to about 110 gai/ha based on the total amount of active ingrédients in the composition. In some embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation with a compound of formula (I) or sait or ester thereof and pinoxaden or sait thereof, e.g., sequentially or simultaneously. In some embodiments, the pinoxaden or sait or ester thereof is applied at a rate from about 2 gai/ha to about 60 gai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha.. In some embodiments, the pinoxaden or sait or ester thereof is applied at a rate from about 15 gai/ha to about 60 gai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 5 gae/ha to about 32 gae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and pinoxaden for the control of ECHCO, IPOHE, KCHSC, PHAMI and SCPJU.

In certain embodiments of the compositions and methods described herein, the compound of formula (I) or sait or ester thereof is used in combination with profoxydim or sait or ester thereof. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to profoxydim or sait or ester thereof is within the range of from about 1:70 to about 29:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to profoxydim or sait or ester thereof is within the range of from 1:8 to about 2:1. In certain embodiments, the weight ratio ofthe compound of formula (I) or sait or ester thereof to profoxydim or sait or ester thereof is within the range of from about 1:10 to about 3:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to profoxydim or sait or ester thereof is within the range of from about 1:23 to about 3:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to profoxydim or sait or ester thereof is within the range of from about 1:5 to about 1.4:1. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl ester and profoxydim. In one embodiment, the composition comprises the compound of formula (I) and profoxydim, wherein the weight ratio of the compound of formula (I) to profoxydim is about 1:3. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and profoxydim, wherein the weight ratio of the benzyl ester of the compound of formula (I) to profoxydim is about 1:5 to about 1.4:1. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 15 grams active ingrédient per hectare (gai/ha) to about 500 gai/ha based on the total amount of active ingrédients in the composition. In certain embodiments, the composition is applied at an application rate of from about 16 grams active ingrédient per hectare (gai/ha) to about 50 gai/ha based on the total amount of active ingrédients in the composition. In some embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation with a compound of formula (I) or sait or ester thereof and profoxydim or sait or ester thereof, e.g., sequentially or simultaneously. In some embodiments, the profoxydim or sait or ester thereof is applied at a rate from about 12 gai/ha to about 200 gai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the profoxydim or sait or ester thereof is applied at a rate from about 4 gai/ha to about 140 gai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 g acid équivalent per hectare (gae/ha) to about 45 gae/ha. In some embodiments, the profoxydim or sait or ester thereof is applied at a rate from about 12.5 gai/ha to about 25 gai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 4.38 g acid équivalent per hectare (gae/ha) to about 17.5 gae/ha. In certain embodiments, the methods utilize the compound of formula (I), or its benzyl or n-butyl ester and profoxydim. In one embodiment, the methods utilize the compound of formula (I) and profoxydim, wherein the compound of formula (I) is applied at a rate of about 4.38 g acid équivalent per hectare (gae/ha), and profoxydim is applied at a rate of about 12.5 gai/ha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and profoxydim, wherein the benzyl ester of the compound of formula (I) is applied at a rate of from about 4.38 g acid équivalent per hectare (gae/ha) to about 17.5 gae/ha, and profoxydim is applied at a rate of about 12.5 gai/ha to about 25 gai/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or sait or ester thereof in combination with profoxydim or sait or ester thereof are used to control ECHCO, ECHCO, SCPJU or LEFCH.

In certain embodiments of the compositions and methods described herein, the compound of formula (I) or sait or ester thereof is used in combination with quizalofop-P-ethyl or carboxylic acid or carboxylate sait thereof or other ester. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to quizalofop-P-ethyl or carboxylic acid or carboxylate sait thereof or other ester is within the range of from about 1:100 to about 12:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to quizalofop-P-ethyl or carboxylic acid or carboxylate sait thereof or other ester is within the range of from 1:8 to about 19:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to quizalofop-P-ethyl or carboxylic acid or carboxylate sait thereof or other ester is within the range of from 1:6 to about 1:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to quizalofop-P-ethyl or carboxylic acid or carboxylate sait thereof or other ester is within the range of from about 1:12 to about 10:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to quizalofop-P-ethyl or carboxylic acid or carboxylate sait thereof or other ester is within the range of from about 1:6 to about 5:1. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl ester and quizalofop-P-ethyl. In one embodiment, the composition comprises the compound of formula (I) and quizalofop-P-ethyl, wherein the weight ratio of the compound of formula (I) to quizalofop-P-ethyl is about 1:6 to about 5:1. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and quizalofop-P-ethyl, wherein the weight ratio of the benzyl ester of the compound of formula (I) to quizalofop-P-ethyl is about 1:6 to about 5:1. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 6 grams active ingrédient per hectare (gai/ha) to about 400 gai/ha based on the total amount of active ingrédients in the composition. In certain embodiments, the composition is applied at an application rate of from about 8 grams active ingrédient per hectare (gai/ha) to about 50 gai/ha based on the total amount of active ingrédients in the composition. In some embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation with a compound of formula (I) or sait or ester thereof and quizalofop-P-ethyl or carboxylic acid or carboxylate sait thereof or other ester, e.g., sequentially or simultaneously. In some embodiments, the quizalofop-P-ethyl or carboxylic acid or carboxylate sait thereof or other ester is applied at a rate from about 4 gai/ha to about 100 gae/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the quizalofop-P- or carboxylic acid or carboxylate sait thereof or other ester is applied at a rate from about 2 gai/ha to about 60 gai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 g acid équivalent per hectare (gae/ha) to about 70 gae/ha. In some embodiments, the quizalofop-Pethyl or carboxylic acid or carboxylate sait thereof or other ester is applied at a rate from about 3.56 gai/ha to about 30 gai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 3.75 g acid équivalent per hectare (gae/ha) to about 35 gae/ha. In certain embodiments, the methods utilize the compound of formula (I), or its benzyl ester and quizalofop-P-ethyl. In one embodiment, the methods utilize the compound of formula (I) and quizalofop-P-ethyl, wherein the compound of formula (I) is appiied at a rate of from about 3.75 g acid équivalent per hectare (gae/ha) to about 35 gae/ha, and quizalofop-P-ethyl is appiied at a rate of about 3.56 gai/ha to about 30 gai/ha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and quizalofop-P-ethyl, wherein the benzyl ester of the compound of formula (I) is appiied at a rate of from about 3.75 g acid équivalent per hectare (gae/ha) to about 17.5 gae/ha, and quizalofop-P-ethyl is appiied at a rate of about 3.56 gai/ha to about 30 gai/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or sait or ester thereof in combination with quizalofop-P-ethyl or carboxylic acid or carboxylate sait thereof or other ester are used to control IPOHE, ECHOR, CYPRO, ECHCG, AVEFA, LOLMU.

In certain embodiments of the compositions and methods described herein, the compound of formula (I) or sait or ester thereof is used in combination with sethoxydim or sait or ester thereof. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to sethoxydim or sait or ester thereof is within the range of from about 1:70 to about 29:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to sethoxydim or sait or ester thereof is within the range of from 1:8 to about 2:1.1 In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to sethoxydim or sait or ester thereof is within the range of from about 1:61 to about 1:2. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to sethoxydim or sait or ester thereof is within the range of from about 1:120 to about 1:3. In certain embodiments, the weight ratio ofthe compound of formula (I) or sait or ester thereof to sethoxydim or sait or ester thereof is within the range of from about 1:54 to about 1:7.7. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl ester and sethoxydim. In one embodiment, the composition comprises the compound of formula (I) and sethoxydim, wherein the weight ratio of the compound of formula (I) to sethoxydim is about 1:54 to about 1:7.7. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and sethoxydim, wherein the weight ratio of the benzyl ester of the compound of formula (I) to sethoxydim is about 1:27 to about 1:15.4. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation a composition described herein. In some embodiments, the composition is appiied at an application rate of from about 55 grams active ingrédient per hectare (gai/ha) to about 825 gai/ha based on the total amount of active ingrédients in the composition. In certain embodiments, the composition is applied at an application rate of from about 55 grams active ingrédient per hectare (gai/ha) to about 300 gai/ha based on the total amount of active ingrédients in the composition. In some embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation with a compound of formula (I) or sait or ester thereof and sethoxydim or sait or ester thereof, e.g., sequentially or simultaneously. In some embodiments, the sethoxydim or sait or ester thereof is applied at a rate from about 50 gai/ha to about 525 gai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the sethoxydim or sait or ester thereof is applied at a rate from about 30 gai/ha to about 600 gai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 g acid équivalent per hectare (gae/ha) to about 45 gae/ha. In some embodiments, the sethoxydim or sait or ester thereof is applied at a rate from about 67.5 gai/ha to about 270 gai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 4.38 g acid équivalent per hectare (gae/ha) to about 17.5 gae/ha. In certain embodiments, the methods utilize the compound of formula (I), or its benzyl ester and sethoxydim. In one embodiment, the methods utilize the compound of formula (I) and sethoxydim, wherein the compound of formula (I) is applied at a rate of from about 4.38 g acid équivalent per hectare (gae/ha) to about 17.5 gae/ha, and sethoxydim is applied at a rate of about 67.5 gai/ha to about 270 gai/ha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and sethoxydim, wherein the benzyl ester of the compound of formula (I) is applied at a rate of from about 4.38 g acid équivalent per hectare (gae/ha) to about 8.75 gae/ha, and sethoxydim is applied at a rate of about 135 gai/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or sait or ester thereof in combination with sethoxydim or sait or ester thereof are used to control CYPES, CYPDI, CYPIR, SCPJU, LEFCH, FIMMI, or ECHCG.

In certain embodiments of the compositions and methods described herein, the compound of formula (I) or sait or ester thereof is used in combination with tralkoxydim or sait or ester thereof. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to tralkoxydim or sait or ester thereof is within the range of from about 1:38 to about 60:1. In certain embodiments, the weight ratio ofthe compound of formula (I) or sait or ester thereof to tralkoxydim or sait or ester thereof is within the range of from 1:23 to about 10:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to tralkoxydim or sait or ester thereof is within the range of from 1:40 to about 1:2. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and tralkoxydim. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 7 grams active ingrédient per hectare (gai/ha) to about 375 gai/ha based on the total amount of active ingrédients in the composition. In certain embodiments, the composition is applied at an application rate of from about 8 grams active ingrédient per hectare (gai/ha) to about 100 gai/ha based on the total amount of active ingrédients in the composition. In some embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation with a compound of formula (I) or sait or ester thereof and tralkoxydim or sait thereof, e.g., sequentially or simultaneously. In some embodiments, the tralkoxydim or sait or ester thereof is applied at a rate from about 5 gai/ha to about 75 gai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and tralkoxydim are used to control AVEFA, CYPIR, KCHSC and LOLMU.

The components of the mixtures described herein can be applied either separately or as part of a multipart herbicidal system.

The mixtures described herein can be applied in conjunction with one or more other herbicides to control a wider variety of undesirable végétation. When used in conjunction with other herbicides, the composition can be formulated with the other herbicide or herbicides, tank mixed with the other herbicide or herbicides or applied sequentially with the other herbicide or herbicides. Some of the herbicides that can be employed in conjunction with the compositions and methods described herein include, but are not limited to: 4-CPA; 4-CPB; 4-CPP; 2,4-D; 2,4D choline sait, 2,4-D esters and amines, 2,4-DB; 3,4-DA; 3,4-DB; 2,4-DEB; 2,4-DEP; 3,4-DP; 2,3,6-TBA; 2,4,5-T; 2,4,5-TB; acetochlor, acifluorfen, aclonifen, acrolein, alachlor, allidochlor, alloxydim, allyl alcohol, alorac, ametridione, ametryn, amibuzin, amicarbazone, amidosulfuron, aminocyclopyrachlor, aminopyralid, amiprofos-methyl, amitrole, ammonium sulfamate, anilofos, anisuron, asulam, atraton, atrazine, azafenidin, azimsulfuron, aziprotryne, barban, BCPC, beflubutamid, benazolin, bencarbazone, benfluralin, benfuresate, bensulfuron-methyl, bensulide, benthiocarb, bentazon-sodium, benzadox, benzfendizone, benzipram, benzobicyclon, benzofenap, benzofluor, benzoylprop, benzthiazuron, bialaphos, bicyclopyrone, bifenox, bilanafos, bispyribac-sodium, borax, bromacil, bromobonil, bromobutide, bromofenoxim, bromoxynil, brompyrazon, butachlor, butafenacil, butamifos, butenachlor, buthidazole, buthiuron, butralin, butroxydim, buturon, butylate, cacodylic acid, cafenstrole, calcium chlorate, calcium cyanamide, cambendichlor, carbasulam, carbetamide, carboxazole chlorprocarb, carfentrazone-ethyl, CDEA, CEPC, chlomethoxyfen, chloramben, chloranocryl, chlorazifop, chlorazine, chlorbromuron, chlorbufam, chloreturon, chlorfenac, chlorfenprop, chlorflurazole, chlorflurenol, chloridazon, chlorimuron, chlomitrofen, chloropon, chlorotoluron, chloroxuron, chloroxynil, chlorpropham, chlorsulfuron, chlorthal, chlorthiamid, cinidon-ethyl, cinmethylin, cinosulfuron, cisanilide, cliodinate, clofop, clomazone, clomeprop, cloprop, cloproxydim, clopyralid, cloransulam-methyl, CMA, copper sulfate, CPMF, CPPC, credazine, cresol, cumyluron, cyanatryn, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cycluron, cyperquat, cyprazine, cyprazole, cypromid, daimuron, dalapon, dazomet, delachlor, desmedipham, desmetryn, di-allate, dicamba, dichlobenil, dichloralurea, dichlormate, dichlorprop, dichlorprop-P, diclosulam, diethamquat, diethatyl, difenopenten, difenoxuron, difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimexano, dimidazon, dinitramine, dinofenate, dinoprop, dinosam, dinoseb, dinoterb, diphenamid, dipropetryn, diquat, disul, dithiopyr, diuron, DMP A, DNOC, DSMA, EBEP, eglinazine, endothal, epronaz, EPTC, erbon, esprocarb, ethalfluralin, ethbenzamide, ethametsulfuron, ethidimuron, ethiolate, ethobenzamid, etobenzamid, ethofumesate, ethoxyfen, ethoxysulfuron, etinofen, etnipromid, etobenzanid, EXD, fenasulam, fenoprop, fenoxasulfone, fenteracol, fenthiaprop, fentrazamide, fenuron, ferrous sulfate, flamprop, flamprop-M, flazasulfuron, florasulam, fluazolate, flucarbazone, flucetosulfuron, fluchloralin, flufenacet, flufenican, flufenpyr-ethyl, flumetsulam, flumezin, flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, fluoromidine, fluoronitrofen, fluothiuron, flupoxam, flupropacil, flupropanate, flupyrsulfuron, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fomesafen, foramsulfuron, fosamine, fumiclorac, furyloxyfen, glufosinate, glufosinate-ammonium, glufosinate-P-ammonium, glyphosate salts and esters, halauxifen, halauxifen-methyl, halosafen, halosulfuron-methyl, haloxydine, hexachloroacetone, hexaflurate, hexazinone, imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazosulfuron, imazethapyr, indanofan, indaziflam, iodobonil, iodomethane, iodosulfuron, iodosulfuron-ethyl-sodium, iofensulfuron, ioxynil, ipazine, ipfencarbazone, iprymidam, isocarbamid, isocil, isomethiozin, isonoruron, isopolinate, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, karbutilate, ketospiradox, lactofen, lenacil, linuron, MAA, ΜΑΜΑ, MCPA esters and amines, MCPA-thioethyl, MCPB, mecoprop, mecoprop-P, medinoterb, mefenacet, mefluidide, mesoprazine, mesosulfuron, mesotrione, metam, metamitron, metazachlor, metazosulfuron, metflurazon, methabenzthiazuron, methalpropalin, methazole, methiobencarb, methiozolin, methiuron, methometon, methoprotryne, methyl bromide, methyl isothiocyanate, methyldymron, metobenzuron, metobromuron, metolachlor, metosulam, metoxuron, metribuzin, metsulfiiron, metsulfiiron-methyl, molinate, monalide, monisouron, monochloroacetic acid, monolinuron, monuron, morfamquat, MSMA, naproanilide, napropamide, naptalam, neburon, nicosulfiiron, nipyraclofen, nitralin, nitrofen, nitrofluorfen, norflurazon, noruron, OCH, orbencarb, orthodichlorobenzene, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxapyrazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraflufen-ethyl, parafluron, paraquat, pebulate, pelargonic acid, pendimethalin, penoxsulam, pentachlorophenol, pentanochlor, pentoxazone, perfluidone, pethoxamid, phenisopham, phenmedipham, phenmedipham-ethyl, phenobenzuron, phenylmercury acetate, picloram, picolinafen, piperophos, potassium arsenite, potassium azide, potassium cyanate, pretilachlor, primisulfuron-methyl, procyazine, prodiamine, profluazol, profluralin, proglinazine, prohexadione-calcium, prometon, prometryn, pronamide, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propyrisulfuron, propyzamide, prosulfalin, prosulfocarb, prosulfuron, proxan, prynachlor, pydanon, pyraclonil, pyraflufen-ethyl, pyrasulfotole, pyrazogyl, pyrazolynate, pyrazosulfuron-ethyl, pyrazoxyfen, pyribenzoxim, pyributicarb, pyriclor, pyridafol, pyridate, pyriftalid, pyriminobac, pyrimisulfan, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quinonamid, rhodethanil, rimsulfuron, saflufenacil, S-metolachlor, sebuthylazine, secbumeton, siduron, simazine, simeton, simetryn, SMA, sodium arsenite, sodium azide, sodium chlorate, sulcotrione, sulfallate, sulfentrazone, sulfometuron, sulfosate, sulfosulfuron, sulfuric acid, sulglycapin, swep, SYN-523, TCA, tebutam, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbuchlor, terbumeton, terbuthylazine, terbutryn, tetrafluron, thenylchlor, thiazafluron, thiazopyr, thidiazimin, thidiazuron, thiencarbazone-methyl, thifensulfuron, thifensulfum-methyl, thiobencarb, tiocarbazil, tioclorim, topramezone, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, tricamba, triclopyr choline sait, triclopyr esters and salts, tridiphane, trietazine, trifloxysulfuron, trifluralin, triflusulfuron, trifop, trifopsime, trihydroxytriazine, trimeturon, tripropindan, tritac tritosulfuron, vemolate, xylachlor and salts, esters, optîcally active isomers and mixtures thereof.

The compositions and methods described herein, can further be used in conjunction with glyphosate, 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, glufosinate, glutamine synthetase inhibitors, dicamba, phenoxy auxins, pyridyloxy auxins, synthetic auxins, auxin transport inhibitors, aryloxyphenoxypropionates, cyclohexanediones, phenylpyrazolines, acetyl CoA carboxylase (ACCase) inhibitors, imidazolinones, sulfonylureas, pyrimidinylthiobenzoates, triazolopyrimidine sulfonamides, sulfonylaminocarbonyltriazolinones, acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors, 4hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, phytoene desaturase inhibitors, carotenoid biosynthesis inhibitors, protoporphyrinogen oxidase (PPO) inhibitors, cellulose biosynthesis inhibitors, mitosis inhibitors, microtubule inhibitors, very long chain fatty acid inhibitors, fatty acid and lipid biosynthesis inhibitors, photosystem I inhibitors, photosystem II inhibitors, triazines, and bromoxynil on glyphosate-tolerant, EPSP synthase inhibitor-tolerant, glufosinate-tolerant, glutamine synthetase inhibitor-tolerant, dicamba-tolerant, phenoxy auxintolerant, pyridyloxy auxin-tolerant, auxin-tolerant, auxin transport inhibitor-tolerant, aryloxyphenoxypropionate-tolerant, cyclohexanedione-tolerant, phenylpyrazoline-tolerant, ACCase-tolerant, imidazolinone-tolerant, sulfonylurea-tolerant, pyrimidinylthiobenzoatetolerant, triazolopyrimidine-tolerant, sulfonylaminocarbonyltriazolinone-tolerant, ALS- or AHAS-tolerant, HPPD-tolerant, phytoene desaturase inhibitor-tolerant, carotenoid biosynthesis inhibitor tolérant, PPO-tolerant, cellulose biosynthesis inhibitor-tolerant, mitosis inhibitortolerant, microtubule inhibitor-tolerant, very long chain fatty acid inhibitor-tolerant, fatty acid and lipid biosynthesis inhibitor-tolerant, photosystem I inhibitor-tolerant, photosystem II inhibitor-tolerant, triazine-tolerant, bromoxynil-tolerant, and crops possessing multiple or stacked traits conferring tolérance to multiple chemistries and/or multiple modes of action via single and/or multiple résistance mechanisms. In some embodiments, the compound of formula (I) or sait or ester thereof and complementary herbicide or sait or ester thereof are used in combination with herbicides that are sélective for the crop being treated and which complément the spectrum of weeds controlled by these compounds at the application rate employed. In some embodiments, the compositions described herein and other complementary herbicides are applied at the same time, either as a combination formulation or as a tank mix.

In some embodiments, the compositions described herein are employed in combination with one or more herbicide safeners, such as AD-67 (MON 4660), benoxacor, benthiocarb, brassinolide, cloquintocet (mexyl), cyometrinil, daimuron, dichlormid, dicyclonon, dimepiperate, disulfoton, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, harpin proteins, isoxadifen-ethyl, jiecaowan, jiecaoxi, mefenpyr-diethyl, mephenate, naphthalic anhydride (NA), oxabetrinil, R29148 and 7V-phenyl-sulfonylbenzoic acid amides, to enhance their selectivity. In some embodiments, the safeners are employed in rice, cereal, corn, or maize settings. In some embodiments, the safener is cloquintocet or an ester or sait thereof. In certain embodiments, cloquintocet is utilized to antagonize harmful effects of the compositions on rice and cereals. In some embodiments, the safener is cloquintocet (mexyl).

In some embodiments, the compositions described herein are employed in combination with one or more plant growth regulators, such as 2,3,5-tri-iodobenzoic acid, IAA, IBA, naphthaleneacetamide, α-naphthaleneacetic acids, benzyladenine, 4-hydroxyphenethyl alcohol, kinetin, zeatin, endothal, ethephon, pentachlorophenol, thidiazuron, tribufos, aviglycine, maleic hydrazide, gibberellins, gibberellic acid, abscisic acid, ancymidol, fosamine, glyphosine, isopyrimol, jasmonic acid, maleic hydrazide, mepiquat, 2,3,5-tri-iodobenzoic acid, morphactins, dichlorflurenol, flurprimidol, mefluidide, paclobutrazol, tetcyclacis, uniconazole, brassinolide, brassinolide-ethyl, cycloheximide, ethylene, methasulfocarb, prohexadione, triapenthenol and trinexapac.

In some embodiments, the plant growth regulators are employed in one or more crops or settings, such as rice, cereal crops, corn, maize , broadleaf crops, oilseed rape/canola, turf, pineapple, sugarcane, sunflower, pastures, grasslands, rangelands, fallowland, tree and vine orchards, plantation crops, vegetables, and non-crop (omamentals) settings. In some embodiments, the plant growth regulator is mixed with the compound of formula (I), or mixed with the compound of formula (I) and ACCase inhibitors to cause a preferentially advantageous effect on plants.

In certain embodiments, the compositions comprise or the methods utilize (a) the compound of formula I or agriculturally acceptable sait or ester thereof; (b) an ACCase inhibitor; and (c) a third herbicide. In some embodiments, the compositions comprise or the methods utilize a compound of Formula I or agriculturally acceptable sait or ester thereof, cyhalofopbutyl, and penoxsulam. In some embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 7 to about 45 weight percent of the total composition; cyhalofop-butyl is from about 48 to about 89 weight percent of the total composition, and penoxsulam is from about 4 to about 7 weight percent of the total composition. In certain embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 9 to about 28 weight percent of the total composition; cyhalofop-butyl is from about 62 to about 88 weight percent of the total composition, and penoxsulam is from about 2 to about 10 weight percent of the total composition. In some embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof, or sait or ester thereof, is applied at a rate from about 2 to about 300 gae/ha (grams acid equivalent/ha); cyhalofop-butyl sait or ester thereof is applied at a rate from about 25 to about 400 gai/ha (grams active ingredient/ha), and penoxsulam is applied from about 1 to about 50 gr ai/ha (grams active ingredient/ha). In a further embodiment, the compound of formula I or agriculturally acceptable sait or ester thereof, is applied at a rate from about 1 to about 32 gae/ha; cyhalofop-butyl sait or ester thereof is applied at a rate from about 25 to about 280 gai/ha, and penoxsulam is applied from about 2 to about 35 gr ai/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or sait or ester thereof in combination with cyhalofopbutyl and penoxsulam, or sait or ester thereof, are used to control ECHCG, CYPRO and FIMMI.

In some embodiments, the compositions comprise or the methods utilize a compound of formula I or agriculturally acceptable sait or ester thereof, cyhalofop-butyl, and bentazonsodium. In some embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 2 to about 13 weight percent ofthe total composition; cyhalofop-butyl is from about 14 to about 20 weight percent of the total composition, and bentazon-sodium is from about 73 to about 78 weight percent of the total composition. In certain embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 1 to about 9 weight percent ofthe total composition; cyhalofop-butyl is from about 15 to about 18 weight percent of the total composition, and bentazon-sodium is from about 78 to about 84 weight percent of the total composition. In some embodiments, the compound of Formula I, or sait or ester thereof, is applied at a rate from about 2 to about 300 gae/ha; cyhalofop-butyl is applied at a rate from about 25 to about 400 gai/ha, and bentazon-sodium is applied from about 1 to about 1,500 gr ai/ha. In a further embodiment, the compound of formula I or agriculturally acceptable sait or ester thereof, is applied at a rate from about 1 to about 32 gae/ha; cyhalofop-butyl sait or ester thereof is applied at a rate from about 25 to about 280 gai/ha, and bentazon-sodium is applied from about 210 to about 1,200 gr ai/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or sait or ester thereof in combination with cyhalofop-butyl and bentazone sodium, or sait or ester thereof, are used to control ECHCG and FIMMI.

In some embodiments, the compositions comprise or the methods utilize a compound of the formula I or agriculturally acceptable sait or ester thereof, cyhalofop-butyl, and triclopyr. In some embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 2 to about 20 weight percent of the total composition; cyhalofop-butyl is from about 20 to about 22 weight percent of the total composition, and bentazon-sodium is from about 58 to about 78 weight percent of the total composition. In certain embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 1 to about 11 weight percent of the total composition; cyhalofop-butyl is from about 15 to about 25 weight percent of the total composition, and triclopyr is from about 64 to about 84 weight percent ofthe total composition. In some embodiments, the compound of Formula I, or sait or ester thereof, is applied at a rate from about 2 to about 300 gae/ha; cyhalofop-butyl is applied at a rate from about to about 400 gai/ha, and triclopyr is applied from about 100 to about 840 gr ae/ha. In a further embodiment, the compound of formula I or agriculturally acceptable sait or ester thereof, is applied at a rate from about 1 to about 32 gae/ha; cyhalofop-butyl sait or ester thereof is applied at a rate from about 25 to about 280 gai/ha, and triclopyr is applied from about 210 to about 560 gr ae/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or sait or ester thereof in combination with cyhalofop-butyl and triclopyr, or sait or ester thereof, are used to control ECHCG and SCPJU.

In some embodiments, the compositions comprise or the methods utilize a compound of formula I or agriculturally acceptable sait or ester thereof, cyhalofop-butyl, and bispyribacsodium. In some embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 4 to about 44 weight percent of the total composition; cyhalofop-butyl is from about 47 to about 53 weight percent of the total composition, and bispyribac-sodium is from about 9 to about 43 weight percent of the total composition. In certain embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 6 to about 28 weight percent of the total composition; cyhalofop-butyl is from about 60 to about 63 weight percent of the total composition, and bispyribac-sodium is from about 11 to about 30 weight percent of the total composition. In some embodiments, the compound of formula I, or sait or ester thereof, is applied at a rate from about 2 to about 300 gae/ha; cyhalofop-butyl is applied at a rate from about 25 to about 400 gai/ha, and bispyribac-sodium is applied from about 20 to about 90 gr ai/ha. In a further embodiment, the compound of formula I or agriculturally acceptable sait or ester thereof, is applied at a rate from about 1 to about 32 gae/ha; cyhalofop-butyl sait or ester thereof is applied at a rate from about 25 to about 280 gai/ha, and bispyribac-sodium is applied from about 25 to about 75 gr ai/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or sait or ester thereof in combination with cyhalofopbutyl and bispyribac-sodium, or sait or ester thereof, are used to control ECHCG and SCPJU.

In some embodiments, the compositions comprise or the methods utilize the compound of formula I, cyhalofop-butyl, and imazamox. In some embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 5 to about 44 weight percent of the total composition; cyhalofop-butyl is from about 46 to about 77 weight percent of the total composition, and imazamox is from about 10 to about 18 weight percent of the total composition. In certain embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 8 to about 28 weight percent of the total composition; cyhalofop-butyl is from about 58 to about 80 weight percent of the total composition, and imazamox is from about 12 to about 14 weight percent of the total composition. In some embodiments, the compound of Formula I, or sait or ester thereof, is applied at a rate from about 2 to about 300 gai/ha; cyhalofop-butyl is applied at a rate from about 25 to about 400 gai/ha, and imazamox is applied from about 6 to about 70 gr ai/ha.

In some embodiments, the compositions comprise or the methods utilize a compound of the formula I or agriculturally acceptable sait or ester thereof, cyhalofop-butyl, and benzobicyclon. In some embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 3 to about 33 weight percent of the total composition; cyhalofop-butyl is from about 32 to about 35 weight percent of the total composition, and benzobicyclon is from about 33 to about 65 weight percent of the total composition. In certain embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 3 to about 19 weight percent ofthe total composition; cyhalofop-butyl is from about 32 to about 42 weight percent of the total composition, and benzobicyclon is from about 39 to about 65 weight percent of the total composition. In some embodiments, the compound of Formula I, or sait or ester thereof, is applied at a rate from about 2 to about 300 gai/ha; cyhalofop-butyl is applied at a rate from about 25 to about 400 gai/ha, and benzobicyclon is applied from about 50 to about 300 gr ai/ha. In a further embodiment, the compound of formula I or agriculturally acceptable sait or ester thereof, is applied at a rate from about 1 to about 32 gae/ha; cyhalofopbutyl sait or ester thereof is applied at a rate from about 25 to about 280 gai/ha, and benzobicyclon is applied from about 50 to about 300 gr ai/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or sait or ester thereof in combination with cyhalofop-butyl and bispyribac-sodium, or sait or ester thereof, are used to control ECHCG, ECHOR and FIMMI.

In some embodiments, the compositions comprise or the methods utilize a compound of the formula I or agriculturally acceptable sait or ester thereof, cyhalofop-butyl, and quinclorac. In some embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 2 to about 25 weight percent of the total composition; cyhalofop-butyl is from about 25 to about 27 weight percent of the total composition, and quinclorac is from about 48 to about 72 weight percent of the total composition. In certain embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 3 to about 14 weight percent of the total composition; cyhalofop-butyl is from about 25 to about 26 weight percent of the total composition, and quinclorac is from about 54 to about 71 weight percent of the total composition. In some embodiments, the compound of formula I, or sait or ester thereof, is applied at a rate from about 2 to about 300 gae/ha; cyhalofop-butyl is applied at a rate from about 25 to about 400 gai/ha, and Quinclorac is applied from about 70 to about 560 gr ai/ha.

In some embodiments, the compositions comprise or the methods utilize a compound of the formula I or agriculturally acceptable sait or ester thereof, cyhalofop-butyl, and glyphosate. In some embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 1 to about 11 weight percent of the total composition; cyhalofopbutyl is from about 11 to about 13 weight percent of the total composition, and glyphosate is from about 78 to about 86 weight percent of the total composition. In certain embodiments the compound of formula I or agriculturally acceptable sait or ester thereof is from about 1.5 to about 5.5 weight percent of the total composition; cyhalofop-butyl is from about 15 to about 11.5 weight percent of the total composition, and glyphosate is from about 83 to about 83.5 weight percent of the total composition. In some embodiments, the compound of Formula I, or sait or ester thereof, is applied at a rate from about 2 to about 300 gae/ha; cyhalofop-butyl is applied at a rate from about 25 to about 400 gai/ha, and glyphosate is applied from about 160 to about 2240 gr ae/ha.

In some embodiments, the compositions comprise or the methods utilize a compound of the formula I or agriculturally acceptable sait or ester thereof, cyhalofop-butyl, and glufosinate. In some embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 4 to about 14 weight percent of the total composition; cyhalofopbutyl is from about 15 to about 45 weight percent of the total composition, and glufosinate is from about 51 to about 71 weight percent of the total composition. In certain embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 4 to about 7 weight percent of the total composition; cyhalofop-butyl is from about 16 to about 38 weight percent of the total composition, and glufosinate is from about 58 to about 77 weight percent of the total composition. In some embodiments, the compound of Formula I, or sait or ester thereof, is applied at a rate from about 2 to about 300 gae/ha; cyhalofop-butyl is applied at a rate from about 25 to about 400 gai/ha, and glufosinate is applied from about 28 to about 1560 gr ai/ha.

In some embodiments, the compositions comprise or the methods utilize a compound of the formula I or agriculturally acceptable sait or ester thereof, fenoxaprop, and penoxsulam. In some embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 7 to about 61 weight percent of the total composition; fenoxaprop is from about 89 to about 29 weight percent of the total composition, and penoxsulam is from about 4 to about 10 weight percent of the total composition. In certain embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 9 to about 44 weight percent of the total composition; fenoxaprop is from about 41 to about 88 weight percent of the total composition, and penoxsulam is from about 3 to about 15 weight percent of the total composition. In some embodiments, the compound of Formula I, or sait or ester thereof, is applied at a rate from about 2 to about 300 gae/ha; fenoxaprop is applied at a rate from about 25 to about 140 gr ae/ha, and penoxsulam is applied from about 1 to about 50 gr ai/ha.

In some embodiments, the compositions comprise or the methods utilize a compound of the formula I or agriculturally acceptable sait or ester thereof, metamifop, and penoxsulam. In some embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 4 to about 46 weight percent of the total composition; metamifop is from about 46 to about 94 weight percent of the total composition, and penoxsulam is from about 2 to about 8 weight percent of the total composition. In certain embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 7 to about 30 weight percent of the total composition; metamifop is from about 60 to about 90 weight percent of the total composition, and penoxsulam is from about 3 to about 10 weight percent of the total composition. In some embodiments, the compound of Formula I, or sait or ester thereof, is applied at a rate from about 2 to about 300 gae/ha; metamifop is applied at a rate from about 10 to about 300 gr ae/ha, and penoxsulam is applied from about 1 to about 50 gr ai/ha. In a further embodiment, the compound of formula I or agriculturally acceptable sait or ester thereof, is applied at a rate from about 1 to about 32 gae/ha; metamifop sait or ester thereof, is applied at a rate from about 25 to about 100 gai/ha, and penoxsulam is applied from about 5 to about 35 gr ai/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or sait or ester thereof in combination with metamifop and penoxsulam, or sait or ester thereof, are used to control ECHCG.

In some embodiments, the compositions comprise or the methods utilize a compound of the formula I or agriculturally acceptable sait or ester thereof, profoxydim, and penoxsulam. In some embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 13 to about 55 weight percent of the total composition; profoxydim is from about 36 to about 80 weight percent of the total composition, and penoxsulam embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 19 to about 39 weight percent of the total composition; profoxydim is from about 50 to about 74 weight percent of the total composition, and penoxsulam is from about 3 to about 10 weight percent ofthe total composition. In some embodiments, the compound of Formula I, or sait or ester thereof, is applied at a rate from about 2 to about 300 gae/ha; profoxydim is applied at a rate from about 12 to about 200 gr ai/ha, and penoxsulam is applied from about 1 to about 50 gr ai/ha.

In some embodiments, the compositions comprise or the methods utilize a compound of the formula I or agriculturally acceptable sait or ester thereof, cyhalofop-butyl, and benfuresate. In some embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 2 to about 32 weight percent of the total composition; cyhalofopbutyl is from about 34 to about 35 weight percent of the total composition, and benfuresate is from about 33 to about 64 weight percent of the total composition. In certain embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 3 to about 19 weight percent of the total composition; cyhalofop-butyl is from about 32 to about 42 weight percent of the total composition, and benfuresate is from about 39 to about 64 weight percent of the total composition. In some embodiments, the compound of Formula I, or sait or ester thereof, is applied at a rate from about 2 to about 300 gae/ha; cyhalofop-butyl, is applied at a rate from about 25 to about 400 gai/ha, and benfuresate is applied from about 50 to 300 gr ai/ha.

In some embodiments, the compositions comprise or the methods utilize a compound of the formula I or agriculturally acceptable sait or ester there of cyhalofop-butyl, and fentrazamide. In some embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 5 to about 33 weight percent of the total composition; cyhalofopbutyl is from about 35 to about 58 weight percent of the total composition, and fentrazamide is from about 32 to about 37 weight percent of the total composition. In certain embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 6 to about 19 weight percent of the total composition; cyhalofop-butyl is from about 39 to about 63 weight percent of the total composition, and fentrazamide is from about 31 to about 40 weight percent of the total composition. In some embodiments, the compound of Formula I, or sait or ester thereof, is applied at a rate from about 2 to about 300 gae/ha; cyhalofop-butyl is applied at a rate from about 25 to about 400 gai/ha, and fentrazamide is applied from about 16 to about 300 gr ai/ha.

In some embodiments, the compositions comprise or the methods utilize a compound of the formula I or agriculturally acceptable sait or ester thereof, cyhalofop-butyl, and indanofan. In some embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 4 to about 33 weight percent of the total composition; cyhalofop-butyl is from about 35 to about 48 weight percent of the total composition, and indanofan is from about 32 to about 48 weight percent of the total composition. In certain embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 5 to about 19 weight percent of the total composition; cyhalofop-butyl is from about 42 to about 48 weight percent of the total composition, and indanofan is from about 39 to about 48 weight percent of the total composition. In some embodiments, the compound of Formula I, or sait or ester thereof, is applied at a rate from about 2 to about 300 gae/ha; cyhalofop-butyl is applied at a rate from about 25 to about 400 gai/ha, and indanofan is applied from about 25 to about 300 gr ai/ha.

In some embodiments, the compositions comprise or the methods utilize a compound of the formula I or agriculturally acceptable sait or ester thereof, cyhalofop-butyl, and ipfencarbazone. In some embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 1 to about 27 weight percent of the total composition; cyhalofop-butyl is from about 9 to about 28 weight percent of the total composition, and ipfencarbazone is from about 45 to about 90 weight percent of the total composition. In certain embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 1 to about 15 weight percent of the total composition; cyhalofop-butyl is from about 14 to about 33 weight percent of the total composition, and ipfencarbazone is from about 52 to about 85 weight percent of the total composition. In some embodiments, the compound of Formula I, or sait or ester thereof, is applied at a rate from about 2 to about 300 gae/ha; cyhalofop-butyl is applied at a rate from about 25 to about 400 gai/ha, and ipfencarbazone is applied from about 250 to about 500 gr ai/ha.

In some embodiments, the compositions comprise or the methods utilize a compound of the formula I or agriculturally acceptable sait or ester thereof, cyhalofop-butyl, and mefenacet. In some embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 1 to about 14 weight percent of the total composition; cyhalofop-butyl is from about 9 to about 14 weight percent of the total composition, and mefenacet is from about 72 to about 90 weight percent of the total composition. In certain embodiments, Formula I is from about 2 to about 7 weight percent of the total composition; cyhalofop-butyl is from about 14 to about 16 weight percent of the total composition, and mefenacet is from about 77 to about 85 weight percent of the total composition. In some embodiments, the compound of Formula I, or sait or ester thereof, is applied at a rate from about 2 to about 300 gae/ha; cyhalofop-butyl is applied at a rate from about 25 to about 400 gai/ha, and mefenacet is applied from about 250 to about 1600 gr ai/ha. In a further embodiment, the compound of formula I or agriculturally acceptable sait or ester thereof, is applied at a rate from about 1 to about 32 gae/ha; cyhalofopbutyl sait or ester thereof is applied at a rate from about 25 to about 280 gai/ha, and mefenacet is applied from about 75 to about 560 gr ai/ha.

In some embodiments, the compositions comprise or the methods utilize a compound of the formula I or agriculturally acceptable sait or ester thereof, cyhalofop-butyl, and oxazichlomafone. In some embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 6 to about 43 weight percent of the total composition;

cyhalofop-butyl is from about 42 to about 76 weight percent of the total composition, and oxazichlomafone is from about 11 to about 18 weight percent of the total composition. In certain embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 7 to about 27 weight percent of the total composition; cyhalofop-butyl is from about 58 to about 77 weight percent of the total composition, and oxazichlomafone is from about 14 to about 15 weight percent of the total composition. In some embodiments, the compound of Formula I, or sait or ester thereof, is applied at a rate from about 2 to about 300 gae/ha; cyhalofop-butyl is applied at a rate from about 25 to about 400 gai/ha, and oxazichlomafone is applied from about 6 to about 80 gr ai/ha. In some embodiments, the compositions comprise or the methods utilize a compound of the formula I or agriculturally acceptable sait or ester thereof, cyhalofop-butyl, or pretilachlor.

In some embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 3 to about 22 weight percent of the total composition; cyhalofop-butyl is from about 23 to about 38 weight percent of the total composition, and pretilachlor is from about 55 to about 58 weight percent of the total composition. In certain embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 3 to about 13 weight percent of the total composition; cyhalofop-butyl is from about 26 to about 32 weight percent of the total composition, and pretilachlor is from about 61 to about 65 weight percent of the total composition. In some embodiments, the compound of Formula I, or sait or ester thereof, is applied at a rate from about 2 to about 300 gae/ha; cyhalofop-butyl is applied at a rate from about 25 to about 400 gai/ha, and pretilachlor is applied from about 38 to about 750 gr ai/ha.

In some embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof, cyhalofop-butyl, and propyrisulfuron. In some embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 5 to about 42 weight percent of the total composition; cyhalofop-butyl is from about 44 to about 66 weight percent of the total composition, and propyrisulfuron is from about 14 to about 29 weight percent of the total composition. In certain embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 7 to about 26 weight percent of the total composition; cyhalofop-butyl is from about 56 to about 66 weight percent of the total composition, and propyrisulfuron is from about 18 to about 27 weight percent of the total composition. In some embodiments, the compound of Formula I, or sait or ester thereof, is applied at a rate from about 2 to about 300 gae/ha; cyhalofop-butyl is applied at a rate from about 25 to about 400 gai/ha, and propyrisulfuron is applied from about 11 to about 100 gr ai/ha.

In some embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof, cyhalofop-butyl, and pyraclonil. In some embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 1 to about 33 weight percent of the total composition; cyhalofop-butyl is from about 12 to about 33 weight percent of the total composition, and pyraclonil is from about 33 to about 87 weight percent of the total composition. In certain embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 2 to about 19 weight percent of the total composition; cyhalofop-butyl is from about 20 to about 42 weight percent of the total composition, and pyraclonil is from about 39 to about 78 weight percent of the total composition. In some embodiments, the compound of Formula I, or sait or ester thereof, is appiied at a rate from about 2 to about 300 gae/ha; cyhalofop-butyl is appiied at a rate from about 25 to about 400 gai/ha, and pyraclonil is appiied from about 180 to about 300 gr ai/ha.

In some embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof, cyhalofop-butyl, and pyriftalid. In some embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 3 to about 42 weight percent of the total composition; cyhalofop-butyl is from about 35 to about 45 weight percent of the total composition, and pyriftalid is from about 13 to about 62 weight percent of the total composition. In certain embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 5 to about 27 weight percent of the total composition; cyhalofop-butyl is from about 47 to about 57 weight percent of the total composition, and pyriftalid is from about 16 to about 48 weight percent of the total composition. In some embodiments, the compound of Formula I, or sait or ester thereof, is appiied at a rate from about 2 to about 300 gae/ha; cyhalofop-butyl is appiied at a rate from about 25 to about 400 gai/ha, and pyriftalid is appiied from about 45 to about 90 gr ai/ha.

In some embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof, cyhalofop-butyl, and pyrimisulfan. In some embodiments, the compound of formula I or agriculturally acceptable sait or ester thereof is from about 7 to about 46 weight percent of the total composition; cyhalofop-butyl is from about 48 to about 85 weight percent of the total composition, and pyrimisulfan is from about 6 to about 8 weight percent of the total composition. In certain embodiments, Formula I is from about 9 to about 29 weight percent of the total composition; cyhalofop-butyl is from about 63 to about 84 weight percent of the total composition, and pyrimisulfan is from about 7 to about 8 weight percent of the total composition. In some embodiments, the compound of Formula I, or sait or ester thereof, is applied at a rate from about 2 to about 300 gae/ha; cyhalofop-butyl is applied at a rate from about 25 to about 320 gai/ha, and pyrimisulfan is applied from about 2.5 to about 40 gr ai/ha.

In some embodiments, the compositions described herein are employed in combination with one or more herbicide safeners, such as AD-67 (MON 4660), benoxacor, benthiocarb, brassinolide, cloquintocet (mexyl), cyometrinil, daimuron, dichlormid, dicyclonon, dimepiperate, disulfoton, fenchlorazole-ethyl, fenclorim, furilazole, fluxofenim, furilazole, harpin proteins, isoxadifen-ethyl, jiecaowan, jiecaoxi, mefenpyr-diethyl, mephenate, naphthalic anhydride (NA), oxabetrinil, R29148 and W-phenyl-sulfonylbenzoic acid amides, to enhance their selectivity. In some embodiments, the safener is cloquintocet or an ester or sait thereof. In certain embodiments, cloquintocet is utilized to antagonize harmful effects of the compositions on rice and cereals. In some embodiments, the safener is cloquintocet (mexyl).

In some embodiments, compositions provided herein further comprise at least one agriculturally acceptable adjuvant or carrier. Suitable adjuvants or carriers should not be phytotoxic to valuable crops, particularly at the concentrations employed in applying the compositions for sélective weed control in the presence of crops, and should not react chemically with herbicidal components or other composition ingrédients. Such mixtures can be designed for application directly to weeds or their locus or can be concentrâtes or formulations that are normally diluted with additional carriers and adjuvants before application. They can be solids, such as, for example, dusts, granules, water-dispersible granules, or wettable powders, or liquids, such as, for example, emulsifiable concentrâtes, solutions, émulsions or suspensions. They can also be provided as a pre-mix or tank mixed.

Suitable agricultural adjuvants and carriers include, but are not limited to, crop oil concentrate; nonylphenol ethoxylate; benzylcocoalkyldimethyl quatemary ammonium sait; blend of petroleum hydrocarbon, alkyl esters, organic acid, and anionic surfactant; C9-C11 alkylpolyglycoside; phosphated alcohol ethoxylate; naturel primary alcohol (Cn-Ciô) ethoxylate; di-sec-butylphenol EO-PO block copolymer; polysiloxane-methyl cap; nonylphenol ethoxylate + urea ammonium nitrate; emulsified methylated seed oil; tridecyl alcohol (synthetic) ethoxylate (8EO); tallow amine ethoxylate (15 EO); PEG(400) dioleate-99.

Liquid carriers that can be employed include water and organic solvents. The organic solvents include, but are not limited to, petroleum fractions or hydrocarbons such as minerai oil, aromatic solvents, paraffinic oils, and the like; vegetable oils such as soybean oil, rapeseed oil, olive oil, castor oil, sunflower seed oil, coconut oil, com oil, cottonseed oil, linseed oil, palm oil, peanut oil, safïlower oil, sesame oil, tung oil and the like; esters of the above vegetable oils;

esters of monoalcohols or dihydric, trihydric, or other lower polyalcohols (4-6 hydroxy containing), such as 2-ethyl hexyl stéarate, n-butyl oleate, isopropyl myristate, propylene glycol dioleate, di-octyl succinate, di-butyl adipate, di-octyl phthalate and the like; esters of mono, di and polycarboxylic acids and the like. Spécifie organic solvents include, but are not limited to toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol monomethyl ether and diethylene glycol monomethyl ether, methyl alcohol, ethyl alcohol, isopropyl alcohol, amyl alcohol, ethylene glycol, propylene glycol, glycérine, W-methyl-2pyrrolidinone, W,JV-dimethyl alkylamides, dimethyl sulfoxide, liquid fertilizers and the like. In certain embodiments, Water is the carrier for the dilution of concentrâtes.

Suitable solid carriers include but are not limited to talc, pyrophyllite clay, silica, attapulgus clay, kaolin clay, kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, Fuller's earth, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, lignin, cellulose, and the like.

In some embodiments, the compositions described herein further comprise one or more surface-active agents. In some embodiments, such surface-active agents are employed in both solid and liquid compositions, and in certain embodiments those designed to be diluted with carrier before application. The surface-active agents can be anionic, cationic or nonionic in character and can be employed as emulsifying agents, wetting agents, suspending agents, or for other purposes. Surfactants which may also be used in the présent formulations are described, inter alia, in “McCutcheon’s Détergents and Emulsifiers Annual,” MC Publishing Corp., Ridgewood, New Jersey, 1998 and in “Encyclopedia of Surfactants,” Vol. I-III, Chemical Publishing Co., New York, 1980-81. Surface-active agents include, but are not limited to salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide additionproducts, such as nonylphenol-Cig ethoxylate; alcohol-alkylene oxide addition products, such as tridecyl alcoholCi6 ethoxylate; soaps, such as sodium stéarate; alkylnaphthalene-sulfonate salts, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl) sulfosuccinate; sorbitol esters, such as sorbitol oleate; quatemary amines, such as lauryl trimethylammonium chloride; polyethylene glycol esters of fatty acids, such as polyethylene glycol stéarate; block copolymers of ethylene oxide and propylene oxide; salts of mono and dialkyl phosphate esters; vegetable or seed oils such as soybean oil, rapeseed/canola oil, olive oil, castor oil, sunflower seed oil, coconut oil, corn oil, cottonseed oil, linseed oil, palm oil, peanut oil, safïlower oil, sesame oil, tung oil and the like; and esters of the above vegetable oils, and in certain embodiments, methyl esters.

In some embodiments, these materials, such as vegetable or seed oils and their esters, can be used interchangeably as an agricultural adjuvant, as a liquid carrier or as a surface active agent.

Other exemplary additives for use in the compositions provided herein include but are not limited to compatibilizing agents, antifoam agents, sequestering agents, neutralizing agents and buffers, corrosion inhibitors, dyes, odorants, spreading agents, pénétration aids, sticking agents, dispersing agents, thickening agents, freezing point depressants, antimicrobial agents, and the like. The compositions may also contain other compatible components, for example, other herbicides, plant growth régulants, fongicides, insecticides, and the like and can be formulated with liquid fertilizers or solid, particulate fertilizer carriers such as ammonium nitrate, urea and the like.

In some embodiments, the concentration of the active ingrédients in the compositions described herein is from about 0.0005 to 98 percent by weight. In some embodiments, the concentration is from about 0.0006 to 90 percent by weight. In compositions designed to be employed as concentrâtes, the active ingrédients, in certain embodiments, are présent in a concentration from about 0.1 to 98 weight percent, and in certain embodiment’s about 0.5 to 90 weight percent. Such compositions are, in certain embodiments, diluted with an inert carrier, such as water, before application. The diluted compositions usually applied to weeds or the locus of weeds contain, in certain embodiments, about 0.0006 to 10.0 weight percent active ingrédient and in certain embodiments contain about 0.01 to 5.0 weight percent.

The présent compositions can be applied to weeds or their locus by the use of conventional ground or aerial dusters, sprayers, and granule applicators, by addition to irrigation or paddy water, and by other conventional means known to those skilled in the art.

The described embodiments and following examples are for illustrative purposes and are not intended to limit the scope of the claims. Other modifications, uses, or combinations with respect to the compositions described herein will be apparent to a person of ordinary skill in the art without departing from the spirit and scope of the claimed subject matter.

Examples

Results in Examples I, II, III, IV VI, and VII are greenhouse trial results. Example I. Evaluation of Postemergence Foliar-Applied Herbicidal Mixtures for Weed Control in Direct Seeded Rice

Seeds or nutlets of the desired test plant species were planted in a soil matrix prepared by mixing a loam or sandy loam soil (e.g., 28.6 percent silt, 18.8 percent clay, and 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 80 to 20 ratio. The soil matrix was contained in plastic pots with a volume of 1 quart and a surface area of 83.6 square centimeters (cm²). When required to ensure good germination and healthy plants, a fongicide treatment and/or other chemical or physical treatment was applied. The plants were grown for 8-22 days in a greenhouse with an approximate 14 hr. photoperiod which was maintained at about 29° C during the day and 26° C during the night. Nutrients (Peters Excel® 15-5-15 5-Ca 2-Mg and iron chelate) were applied in the irrigation solution as needed and water was added on a regular basis. Supplémentai lighting was provided with overhead métal halide 1000-Watt lamps as necessary. The plants were empioyed for testing when they reached the first through fourth true leaf stage.

Treatments consisted of the acid or esters of 4-amino-3-chloro-5-fluoro-6-(4-chloro-2fluoro-3-methoxy-phenyl)pyridine-2-carboxylic acid (Compound A), each formulated as an SC (suspension concentrate), and various herbicidal components alone and in combination. Forms of compound A were applied on an acid équivalent basis.

Forms of compound A (compound of formula I) tested include:

nh₂

JL

JL YL .oh N il

O

F h₃ct

Compound A Acid

Compound A Benzyl Ester

Other herbicidal components were applied on an acid équivalent (ae) or active ingrédient (ai) basis and included acetyl coA carboxylase (ACCase)-inhibiting herbicides (cyclohexanedione and aryloxyphenoxypropionate chemical classes) cyhalofop-butyl formulated as Clincher® SF (285 gr ai/L EC), diclofop-methyl formulated as Hoelon® 3EC, fenoxaprop-pethyl + isoxadifen-ethyl formulated as RiceStar® HT (0.58 lb./gal EC), fenoxaprop-p-ethyl + mefenpyr diethyl formulated as Puma® IEC, metamifop formulated as Metamifop EC, haloxyfop-methyl formulated as Gallant Super®, fluazifop-p-butyl formulated as Fusilade® DX, quizalofop-p-ethyl formulated as Assure® II, profoxydim formulated as Aura® 20EC, clethodim applied as Intensity®, sethoxydim formulated as Poast®,and tralkoxydim formulated as Achieve®.

Treatment requirements were calculated based upon the rates being tested, the concentration of active ingrédient or acid équivalent in the formulation, and a 12 mL application volume at a rate of 187 L/ha.

For treatments comprised of formulated compounds, measured amounts of compounds were placed individually in 25 mL glass vials and diluted in a volume of 1.25% (v/v) Agri-Dex® crop oil concentrated to obtain 12X stock solutions. If a test compound did not dissolve readily, the mixture was warmed and/or sonicated. Application solutions were prepared by adding an appropriate 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 1.25% (v/v) crop oil concentrate so that the final spray solutions contained 1.25+/-0.05% (v/v) crop oil concentrate.

For treatments comprised of technical compounds, weighed amounts can be placed individually in 25 mL glass vials and dissolved in a volume of 97:3 v/v acetone/DMSO 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 appropriate 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 concentrated stock solutions can be added to the spray solutions so that the final acetone and DMSO concentrations of the application solutions are 16.2% and 0.5%, respectively.

For treatments comprised of formulated and technical compounds, weighed amounts of the technical materials can be placed individually in 25 mL glass vials and dissolved in a volume of 97:3 v/v acetone/DMSO to obtain 12X stock solutions, and measured amounts ofthe formulated compounds 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 appropriate 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/or 97:3 v/v acetone/DMSO can be added to individual application solutions so that the final acetone and DMSO concentrations of the application solutions being compared are 8.1 % and 0.25%, respectively.

All stock solutions and applications solutions were visually inspected for compound compatibility prior to application. Spray solutions were applied to the plant material with an overhead Mandel track sprayer equipped with a 8002E nozzles calibrated to deliver 187 L/ha over an application area of 0.503 m² at a spray height of 18 to 20 inches (46 to 50 cm) above average plant canopy height. Control plants were sprayed in the same manner with the solvent blank.

The treated plants and control plants were placed in a greenhouse as described above and watered by sub-irrigation to prevent wash-off of the test compounds. 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 complété kill.

Colby’s équation was used to détermine the herbicidal effects expected from the mixtures (Colby, S.R. 1967. Calculation of the synergistic and antagonistic response of herbicide combinations. Weeds 15:20-22.).

The following équation was used to calculate the expected activity of mixtures containing two active ingrédients, A and B:

Expected = A + B - (A x B/100)

A = observed efficacy of active ingrédient A at the same concentration as used in the mixture.

B = observed efficacy of active ingrédient B at the same concentration as used in the mixture.

The compounds tested, application rates employed, plant species tested, and results are given in Tables 1 -21.

Table 1. Synergistic Activity ofFoliar-Applied Compound A Acid and Cyhalofop-Butyl Herbicidal Compositions on Weed Control in a Rice Cropping System.

Compound A Acid	Cyhalofopbutyl	Visual Weed Control (%) - 26 DAA
		ISCRU
gae/ha	gai/ha	Obs	Exp
8.75	0	37	-
17.5	0	63	-
0	140	10	-

8.75	140	63	43
17.5	140	82	67

Compound A Acid	Cyhalofopbutyl	Visual Weed Control (%) - 20 DAA
		IPOHE
gae/ha	gai/ha	Obs	Exp
19.4	0	15	-
0	280	0	-
19.4	280	55	15

Table 2. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Cyhalofop-Butyl Herbicidal Compositions on Weed Control in a Rice Cropping System.

Compound A Benzyl Ester	Cyhalofopbutyl	Visual Weed Control (%) - 26 DAA
		ISCRU
gae/ha	gai/ha	Obs	Exp
8.75	0	18	-
17.5	0	33	-
0	140	10	-
8.75	140	53	27
17.5	140	40	40

Table 3. Synergistic Activity of Foliar-Applied Compound A Acid and Fenoxaprop-p-ethyl + Isoxadifen-ethyl Herbicidal Compositions on Weed Control in a Rice Cropping System.

Compound A Acid	Fenoxapropp-ethyl + Isoxadifenethyl	Visual Weed Control (%) - 20 DAA
		CYPDI
gae/ha	gai/ha*	Obs	Exp
4.38	0	80	-
0	17.5	0	-
0	35	0	-
0	70	0	-
4.38	17.5	70	80
4.38	35	99	80
4.38	70	95	80

Compound A Acid	Fenoxapropp-ethyl + Isoxadifenethyl	Visual Weed Control (%) - 20 DAA
		CYPES
gae/ha	gai/ha*	Obs	Exp
4.38	0	30
8.75	0	70
0	17.5	0
0	35	0
0	70	0
4.38	17.5	30	30
8.75	17.5	100	70
4.38	35	40	30
8.75	35	90	70
4.38	70	80	30
8.75	70	99	70

Compound A Acid	Fenoxapropp-ethyl + Isoxadifenethyl	Visual Weed Control (%) - 20 DAA
		SCPJU
gae/ha	gai/ha*	Obs	Exp
4.38	0	60	-
0	17.5	50	-
0	35	30	-
0	70	30	-
4.38	17.5	100	80
4.38	35	95	72
4.38	70	95	72

*gai/ha refers to concentration of fenoxaprop-p-ethyl

Table 4. Synergistic Activity ofFoliar-Applied Compound A Benzyl Ester and Fenoxaprop-pethyl + Isoxadifen-ethyl Herbicidal Compositions on Weed Control in a Rice Cropping System.

Compound A Benzyl Ester	Fenoxaprop-pethyl + Isoxadifenethyl	Visual Weed Control (%) - 20 DAA
		CYPES
gae/ha	gai/ha*	Obs	Exp
4.38	0	70
8.75	0	80
17.5	0	95
0	17.5	0
0	35	0
0	70	0
4.38	17.5	80	70
8.75	17.5	95	80
17.5	17.5	95	95
4.38	35	80	70
8.75	35	90	80
17.5	35	99	95
4.38	70	80	70
8.75	70	95	80
17.5	70	100	95

Compound A Benzyl Ester	Fenoxaprop-pethyl + Isoxadifenethyl	Visual Weed Control (%) - 20 DAA
		CYPIR
gae/ha	gai/ha*	Obs	Exp

4.38	0	15	-
0	17.5	0	-
0	35	0	-
0	70	0	-
4.38	17.5	70	15
4.38	35	60	15
4.38	70	70	15

*gai/ha refers to concentration of fenoxaprop-p-ethyl

Table 5. Synergistic Activity ofFoliar-Applied Compound A Benzyl Ester and Fenoxaprop-p· ethyl + Mefenpyr-diethyl Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.

Compound A Benzyl Ester	Fenoxaprop-pethyl + Mefenpyrdiethyl	Visual Weed Control (%) - 20 DAA
		CYPIR
gae/ha	gai/ha*	Obs	Exp
8.75	0	35	-
0	11.5	0	-
0	23	0	-
0	46	0	-
8.75	11.5	80	35
8.75	23	85	35
8.75	46	50	35

♦gai/ha refers to concentration of fenoxaprop-p-ethyl

Table 6. Synergistic Activity ofFoliar-Applied Compound A Acid and Haloxyfop-methyl Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.

Compound A Acid	Haloxyfopmethyl	Visual Weed Control (%) - 20 DAA
		ECHCO	IPOHE
gae/ha	gai/ha	Obs	Exp	Obs	Exp
4.38	0	40		10	-
8.75	0	60		30	-
17.5	0	85		40	-
0	6.75	0		0	-
0	13.5	0		0	-
0	27	0		0	-
4.38	6.75	60	40	10	10
8.75	6.75	65	60	30	30
17.5	6.75	70	85	60	40

4.38	13.5	60	40	30	10
8.75	13.5	85	60	35	30
17.5	13.5	95	85	55	40
4.38	27	40	40	20	10
8.75	27	75	60	40	30
17.5	27	99	85	60	40

Compound A Acid	Haloxyfopmethyl	Visual Weed Control (%) - 20 DAA
		SCPJU
gae/ha	gai/ha	Obs	Exp
4.38	0	70
8.75	0	95
0	6.75	0
0	13.5	0
0	27	0
4.38	6.75	100	70
8.75	6.75	100	95
4.38	13.5	100	70
8.75	13.5	100	95
4.38	27	100	70
8.75	27	100	95

Table 7. Synergistic Activity ofFoliar-Applied Compound A Benzyl Ester and Haloxyfopmethyl Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.

Compound A Benzyl Ester	Haloxyfopmethyl	Visual Weed Control (%) - 20 DAA
		BRAPP
gae/ha	gai/ha	Obs	Exp
4.38	0	50	-
8.75	0	70	-
0	6.75	0	-
0	13.5	0	-
4.38	6.75	60	50
8.75	6.75	70	70
4.38	13.5	70	50
8.75	13.5	85	70

Compound A Benzyl Ester

Haloxyfopmethyl

Visual Weed Control (%) - 20 DAA

		SCPJU
gae/ha	gai/ha	Obs	Exp
4.38	0	30
8.75	0	60
0	6.75	0
0	13.5	0
0	27	0
4.38	6.75	100	30
8.75	6.75	100	60
4.38	13.5	99	30
8.75	13.5	100	60
4.38	27	90	30
8.75	27	100	60

Table 8. Synergistic Activity of Foliar-Applied Compound A Acid and Metamifop Herbicidal Compositions on Weed Control in a Rice Cropping System.

Compound A Acid	Metamifop	Visual Weed Control (%) - 24 DAA
		IPOHE
gae/ha	gai/ha	Obs	Exp
4.38	0	10	-
8.75	0	10	-
17.5	0	30	-
0	150	0	-
4.38	150	15	10
8.75	150	25	10
17.5	150	40	30

Table 9. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Metamifop Herbicidal Compositions on Weed Control in a Rice Cropping System.

Compound A Benzyl Ester	Metamifop	Visual Weed Control (%) - 22 DAA
		ECHCG
gae/ha	gai/ha	Obs	Exp
8	0	35
16	0	65
32	0	80
0	9.38	0
0	18.75	40
0	37.5	70

8	9.38	60	35
16	9.38	80	65
32	9.38	90	80
8	18.75	85	61
16	18.75	95	79
32	18.75	99	88
8	37.5	100	81
16	37.5	100	90
32	37.5	99	94

Compound A Benzyl Ester	Metamifop	Visual Weed Control (%) - 22 DAA
		IPOHE
gae/ha	gai/ha	Obs	Exp
32	0	45	-
0	9.38	0	-
0	18.75	0	-
0	37.5	0	-
32	9.38	50	45
32	18.75	60	45
32	37.5	65	45

Table 10. Synergistic Activity ofFoliar-Applied Compound A Acid and Fluazifop-p-butyl

Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.

Compound A Acid	Fluazifop-pbutyl	Visual Weed Control (%) -19 DAA
		IPOHE
gae/ha	gae/ha	Obs	Exp
4.38	0	0
8.75	0	10
17.5	0	35
0	45	0
0	90	0
0	180	0
4.38	45	10	0
8.75	45	10	10
17.5	45	50	35
4.38	90	10	0
8.75	90	25	10
17.5	90	15	35
4.38	180	10	0

8.75	180	35	10
17.5	180	40	35

Table 11. Synergistic Activity ofFoliar-Applied Compound A Benzyl Ester and Fluazifop-p butyl Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.

Compound A Benzyl Ester	Fluazifop-pbutyl	Visual Weed Control (%) -19 DAA
		IPOHE
gae/ha	gae/ha	Obs	Exp
4.38	0	0
8.75	0	0
0	45	0
0	90	0
0	180	0
4.38	45	10	0
8.75	45	20	0
4.38	90	15	0
8.75	90	20	0
4.38	180	20	0
8.75	180	10	0

Table 12. Synergistic Activity ofFoliar-Applied Compound A Acid and Quizalofop-p-ethyl Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.

Compound A Acid	Quizalofopp-ethyl	Visual Weed Control (%) - 20 DAA
		IPOHE
gae/ha	gai/ha	Obs	Exp
4.38	0	0
8.75	0	20
17.5	0	40
0	15	0
0	30	0
4.38	15	NT	0
8.75	15	45	20
17.5	15	70	40
4.38	30	60	0
8.75	30	90	20
17.5	30	70	40

Table 13. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Quizalofop-pethyl Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.

Compound A Benzyl Ester	Quizalofopp-ethyl	Visual Weed Control (%) - 22 DAA
		ECHCG
gae/ha	gai/ha	Obs	Exp
8	0	35
16	0	65
32	0	80
0	3.75	20
0	7.5	30
8	3.75	85	48
16	3.75	65	72
32	3.75	85	84
8	7.5	85	55
16	7.5	100	76
32	7.5	100	86

Compound A Benzyl Ester	Quizalofopp-ethyl	Visual Weed Control (%) - 22 DAA
		IPOHE
gae/ha	gai/ha	Obs	Exp
32	0	45	-
0	1.88	0	-
0	3.75	0	-
0	7.5	0	-
32	1.88	60	45
32	3.75	60	45
32	7.5	50	45

Table 14. Synergistic Activity ofFoliar-Applied Compound A Benzyl Ester and Diclofopmethyl Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.

Compound A Benzyl Ester	Diclofopmethyl	Visual Weed Control (%) - 22 DAA
		CYPIR
gae/ha	gai/ha	Obs	Exp
8	0	20
16	0	85
32	0	100
0	280	0
0	560	0
0	1120	0
8	280	30	20
16	280	100	85
32	280	100	100
8	560	35	20
16	560	75	85
32	560	100	100
8	1120	50	20
16	1120	100	85
32	1120	100	100

Table 15. Synergistic Activity ofFoliar-Applied Compound A Acid and Profoxydim Herbicidal Compositions on Weed Control in a Rice Cropping System.

Compound A Acid	Profoxydim	Visual Weed Control (%) - 20 DAA
		ECHCO
gae/ha	gai/ha	Obs	Exp
4.38	0	40	-
0	12.5	70	-
4.38	12.5	99	82

Table 16. Synergistic ActivityofFoliar-Applied Compound A Benzyl Ester and Profoxydim 10 Herbicidal Compositions on Weed Control in a Rice Cropping System.

Compound A Benzyl Ester	Profoxydim	Visual Weed Control (%) - 20 DAA
		LEFCH

gae/ha	gai/ha	Obs	Exp
4.38	0	0
8.75	0	10
17.5	0	25
0	12.5	0
0	25	40
4.38	12.5	10	0
8.75	12.5	30	10
17.5	12.5	50	25
4.38	25	50	40
8.75	25	50	46
17.5	25	70	55

Table 17. Synergistic Activity of Foliar-Applied Compound A Acid and Sethoxydim Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.

Compound A Acid	Sethoxydim	Visual Weed Control (%) - 22 DAA
		CYPES
gae/ha	gai/ha	Obs	Exp
4.38	0	50
8.75	0	75
0	67.5	0
0	135	0
0	270	0
4.38	67.5	80	50
8.75	67.5	80	75
4.38	135	70	50
8.75	135	100	75
4.38	270	100	50
8.75	270	70	75

Compound A Acid	Sethoxydim	Visual Weed Control (%) - 22 DAA
		CYPDI	CYPIR	SCPJU
gae/ha	gai/ha	Obs	Exp	Obs	Exp	Obs	Exp
4.38	0	60	-	15	-	60	-
0	67.5	0	-	0	-	0	-
0	135	0	-	0	-	0	-
0	270	0	-	0	-	0	-
4.38	67.5	100	60	80	15	80	60
4.38	135	100	60	80	15	85	60

4.38 270

60 60 15 70 60

Table 18. Synergistic Activity ofFoliar-Applied Compound A Benzyl Ester and Sethoxydim Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.

Compound A Benzyl Ester	Sethoxydim	Visual Weed Control (%) - 22 DAA
		ECHCG
gae/ha	gai/ha	Obs	Exp
8	0	35
16	0	65
32	0	80
0	56	30
0	112	90
8	56	90	55
16	56	99	76
32	56	95	86
8	112	100	94
16	112	99	97
32	112	100	98

Compound A Benzyl Ester	Sethoxydim	Visual Weed Control (%) - 22 DAA
		LEFCH
gae/ha	gai/ha	Obs	Exp
8	0	15	-
16	0	50	-
0	112	70	-
8	112	100	75
16	112	100	85

Table 19. Synergistic Activity ofFoliar-Applied Compound A Benzyl Ester and Tralkoxydim Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.

Compound A Benzyl Ester	Tralkoxydim	Visual Weed Control (%) - 22 DAA
		CYPIR
gae/ha	gai/ha	Obs	Exp
8	0	20	-
16	0	85	-

32	0	100	-
0	100	0	. -
0	200	0	-
8	100	20	20
16	100	100	85
32	100	90	100
8	200	100	20
16	200	60	85
32	200	100	100

Table 20. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Pinoxaden Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.

Compound A Benzyl Ester	Pinoxaden	Visual Weed Control (%) - 21 DAA
		ECHCO
gae/ha	gai/ha	Obs	Exp
8	0	40
16	0	70
32	0	95
0	15	15
0	30	85
0	60	95
8	15	75	49
16	15	85	75
32	15	95	96
8	30	95	91
16	30	95	96
32	30	95	99
8	60	100	97
16	60	100	99
32	60	100	100

Compound A Benzyl Ester	Pinoxaden	Visual Weed Control (%) - 21 DAA
		IPOHE
gae/ha	gai/ha	Obs	Exp
16	0	10
32	0	25
0	15	10
0	30	10
0	60	0

16	15	20	19
32	15	60	33
16	30	25	19
32	30	40	33
16	60	15	10
32	60	50	25

Compound A Benzyl Ester	Pinoxaden	Visual Weed Control (%) - 21 DAA
		SCPJU
gae/ha	gai/ha	Obs	Exp
8	0	85	-
0	15	0	-
0	30	0	-
0	60	0	-
8	15	99	85
8	30	100	85
8	60	100	85

Table 21. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Clethodim Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.

Compound A Benzyl Ester	Clethodim	Visual Weed Control (%) - 20 DAA
		BRAPP	DIGSA
gae/ha	gai/ha	Obs	Exp	Obs	Exp
8	0	70	-	15	-
16	0	75	-	25	-
32	0	90	-	35	-
0	70	10	-	50	-
8	70	100	73	75	58
16	70	100	78	80	63
32	70	100	91	85	68

Compound A Benzyl Ester	Clethodim	Visual Weed Control (%) - 20 DAA
		CYPES
gae/ha	gai/ha	Obs	Exp
8	0	0	-
16	0	75	-
0	70	0	-

0	140	0	-
0	280	0	-
8	70	60	0
16	70	85	75
8	140	80	0
16	140	95	75
8	280	95	0
16	280	90	75

Compound A Benzyl Ester	Clethodim	Visual Weed Control (%) - 20 DAA
		SCPJU
gae/ha	gai/ha	Obs	Exp
8	0	70	-
16	0	85	-
0	140	0	-
0	280	0	-
8	140	100	70
16	140	100	85
8	280	100	70
16	280	85	85

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BRAPP Brachiaria platyphylla (Griseb.) Nash

CYPDI Cyperus difformis L.

CYPES Cyperus esculentus L.

CYPIR Cyperus iria L.

DIGSA Digitaria sanguinalis (L.) Scop.

ECHCG Echinochloa crusgalli (L.) Beauv.

ECHCO Echinochloa colona (L.) Link

IPOHE Ipomoea hederacea Jacq.

ISCRU Ischaemum rugosum Salisb.

LEFCH Leptochloa chinensis (L.) Nees

SCPJU Schoenoplectus juncoides (Roxb.) Palla gae/ha = grams acid équivalent per hectare gai/ha = grams active ingrédient per hectare Obs = observed value

Exp = expected value as calculated by Colby’s équation DAA = days after application

NT = not tested signalgrass, broadleaf sedge, smallflower umbrella nutsedge, yellow flatsedge, rice crabgrass, large bamyardgrass junglerice momingglory, ivyleaf saramollagrass sprangletop, Chinese bulrush, Japanese

Exampie II. Evaluation ofln-Water Applied Herbicidal Mixtures for Weed Control in Transplanted Paddy Rice

Weed seeds or nutlets of the desired test plant species were planted in puddled soil (mud) prepared by mixing a shredded, non-sterilized minerai soil (50.5 percent silt, 25.5 percent clay, and 24 percent sand, with a pH of about 7.6 and an organic matter content of about 2.9 percent) and water at a 1:1 volumétrie ratio. The prepared mud was dispensed in 365 mL aliquots into

A 16-ounce (oz.) non-perforated plastic pots with a surface area of 86.59 square centimeters (cm ) leaving a headspace of 3 centimeters (cm) in each pot. Mud was allowed to dry ovemight prior to planting or transplanting. Rice seeds were planted in Sun Gro MetroMix® 306 planting mixture, which typically has a pH of 6.0 to 6.8 and an organic matter content of about 30 percent, in plastic plug trays. Seedlings at the second or third leaf stage of growth were transplanted into 860 mL of mud contained in 32-oz. non-perforated plastic pots with a surface area of 86.59 cm² 4 days prior to herbicide application. The paddy was created by filling the headspace of the pots with 2.5 to 3 cm of water. When required to ensure good germination and healthy plants, a fungicide treatment and/or other chemical or physical treatment was applied. The plants were grown for 4-22 days in a greenhouse with an approximate 14 hr. photoperiod which was maintained at about 29 C during the day and 26°C during the night. Nutrients were added as Osmocote® (19:6:12, N:P:K + minor nutrients) at 2 g per 16-oz. pot and 4 g per 32-oz. pot. Water was added on a regular basis to maintain the paddy flood, and supplémentai lighting was provided with overhead métal halide 1000-Watt lamps as necessary. The plants were employed for testing when they reached the first through fourth true leaf stage.

Treatments consisted ofthe acid or esters of4-amino-3-chloro-5-fluoro-6-(4-chloro-2fluoro-3-methoxy-phenyl)pyridine-2-carboxylic acid (compound A) each formulated as an SC (suspension concentrate) and various herbicidal components alone and in combination. Forms of compound A were applied on an acid équivalent basis.

Forms of compound A (compound of formula I) tested include:

Compound A Acid

Compound A Benzyl Ester

Other herbicidal components were appiied on an acid équivalent (ae) or active ingrédient (ai) basis as to normal practice used in the market, and included acetyl CoA carboxylase (ACCase) inhibiting herbicides (cyclohexanedione and aryloxyphenoxypropionate chemical classes) cyhalofop-butyl formulated as Clincher® EC, fenoxaprop-p-ethyl + isoxadifen-ethyl formulated as RiceStar® HT, fenoxaprop-p-ethyl + mefenpyr diethyl formulated as Puma IEC, metamifop formulated as Metamifop EC, haloxyfop-methyl formulated as Gallant Super®, fluazifop-p-butyl formulated as Fusilade® DX, quizalofop-p-ethyl formulated as Assure® II, profoxydim formulated as Aura® 20EC, and sethoxydim formulated as Poast®.

Treatment requirements for each compound or herbicidal component were calculated based upon the rates being tested, the concentration of active ingrédient or acid équivalent in the formulation, an application volume of 2 mL per component per pot, and an application area of 86.59 cm² per pot.

For formulated compounds, a measured amount was placed in an individual 100 or 200 mL glass vial and was dissolved in a volume of 1.25% (v/v) Agri-Dex® crop oil concentrate to obtain application solutions. If the test compound did not dissolve readily, the mixture was warmed and/or sonicated.

For technical grade compounds, a weighed amount can be placed in an individual 100 to 200 mL glass vial and dissolved in a volume of acetone to obtain concentrated stock solutions. If the test compound does not dissolve readily, the mixture can be warmed and/or sonicated. The concentrated stock solutions obtained can be diluted with an équivalent volume of an aqueous mixture containing 2.5% (v/v) crop oil concentrate so that the final application solutions contain 1.25% (v/v) crop oil concentrate.

Applications were made by injecting with a pipetter appropriate amounts of the application solutions, individually and sequentially, into the aqueous layer of the paddy. Control plants were treated in the same manner with the solvent blank. Applications were made so that ail treated plant material received the same concentrations of acetone and crop oil concentrate.

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 complété kill.

The following équation was used to calculate the expected activity of mixtures containîng two active ingrédients, A and B:

Expected = A + B - (A x B/l 00)

A = observed efïicacy of active ingrédient A at the same concentration as used in the mixture.

B = observed efïicacy of active ingrédient B at the same concentration as used in the mixture.

Some of the compounds tested, application rates employed, plant species tested, and results are given in Tables 22-39.

Table 22. Synergistic Activity of In-Water Applications of Compound A Acid and Cyhalofopbutyl Herbicidal Compositions on Weed Control in a Rice Cropping System.

Compound A Acid	Cyhalofopbutyl	Visual Weed Control (%) - 25 DAA
		ECHOR
gae/ha	gai/ha	Obs	Exp
8.75	0	0	-
17.5	0	0	-
35	0	40	-
0	90	0	-
8.75	90	100	0
17.5	90	100	0
35	90	100	40

Compound A Acid	Cyhalofopbutyl	Visual Weed Control (%) - 25 DAA
		SCPJU
gae/ha	gai/ha	Obs	Exp
8.75	0	65	-
17.5	0	80	-

35	0	95	-
0	90	0	-
0	180	0	-
8.75	90	95	65
17.5	90	95	80
35	90	100	95
8.75	180	95	65
17.5	180	95	80
35	180	95	95

Compound A Acid	Cyhalofopbutyl	Visual Weed Control (%) -19 DAA
		LEFCH
gae/ha	gai/ha	Obs	Exp
42.4	0	10	-
0	180	75	-
42.4	180	90	78

Table 23. Synergistic Activity of In-Water Applications of Compound A Benzyl Ester and Cyhalofop-butyl Herbicidal Compositions on Weed Control in a Rice Cropping System.

Compound A Benzyl Ester	Cyhalofopbutyl	Visual Weed Control (%) - 25 DAA
		ECHOR
gae/ha	gai/ha	Obs	Exp
8.75	0	85	-
17.5	0	90	-
35	0	100	-
0	90	0	-
8.75	90	100	85
17.5	90	100	90
35	90	100	100

Compound A Benzyl Ester	Cyhalofopbutyl	Visual Weed Control (%) -19 DAA
		SCPMA
gae/ha	gai/ha	Obs	Exp
35	0	0	-
0	180	0	-
35	180	50	0

Table 24. Synergistic Activity of In-Water Applications of Compound A Acid and Fenoxaprop p-ethyl + Isoxadifen-ethyl Herbicidal Compositions on Weed Control in a Rice Cropping System.

Compound A Acid	Fenoxapropp-ethyl + Isoxadifenethyl	Visual Weed Control (%) - 21 DAA
		ECHOR
gae/ha	gai/ha	Obs	Exp
8.75	0	0	-
17.5	0	10	-
35	0	15	-
0	70	50	-
8.75	70	100	50
17.5	70	50	55
35	70	100	58

Compound A Acid	Fenoxapropp-ethyl + Isoxadifenethyl	Visual Weed Control (%) - 21 DAA
		FIMMI
gae/ha	gai/ha	Obs	Exp
8.75	0	20	-
0	35	0	-
0	70	0	-
8.75	35	100	20
8.75	70	60	20

Compound A Acid	Fenoxapropp-ethyl + Isoxadifenethyl	Visual Weed Control (%) - 21 DAA
		SCPJU
gae/ha	gai/ha	Obs	Exp
8.75	0	65	-
17.5	0	90	-
0	35	0	-
0	70	0	-
8.75	35	80	65
17.5	35	99	90
8.75	70	85	65
17.5	70	95	90

Table 25. Synergistic Activity of In-Water Applications of Compound A Benzyl Ester and Fenoxaprop-p-ethyl + Isoxadifen-ethyl Herbicidal Compositions on Weed Control in a Rice Cropping System.

Compound A Benzyl Ester	Fenoxaprop-p-ethyl + Isoxadifen-ethyl	Visual Weed Control (%) - 21 DAA
		ECHOR
gae/ha	gai/ha	Obs	Exp
4.38	0	0	-
8.75	0	10	-
17.5	0	60	-
0	70	50	-
4.38	70	100	50
8.75	70	100	55
17.5	70	100	80

Compound A Benzyl Ester	Fenoxapropp-ethyl + Isoxadifenethyl	Visual Weed Control (%) - 21 DAA
		CYPRO
gae/ha	gai/ha	Obs	Exp
4.38	0	20	-
0	35	0	-
0	70	0	-
4.38	35	99	20
4.38	70	50	20

Table 26. Synergistic Activity of In-Water Applications of Compound A Acid and Fenoxapropp-ethyl + Mefenpyr-diethyl Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.

Compound A Acid	Fenoxaprop-pethyl + Mefenpyr diethyl	Visual Weed Control (%) - 21 DAA
		ECHOR
gae/ha	gai/ha	Obs	Exp
10.6	0	0	-
21.2	0	15	-
42.4	0	15	-
0	23	0	-

10.6	23	25	0
21.2	23	15	15
42.4	23	40	15

Table 27. Synergistic Activity of In-Water Applications of Compound A Benzyl Ester and Fenoxaprop-p-ethyl + Mefenpyr-diethyl Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.

Compound A Benzyl Ester	Fenoxaprop-pethyl + Mefenpyrdiethyl	Visual Weed Control (%) - 21 DAA
		ECHOR
gae/ha	gai/ha	Obs	Exp
8	0	10	-
16	0	25	-
32	0	35	-
0	23	15	-
8	23	100	24
16	23	20	36
32	23	75	45

Table 28. Synergistic Activity of In-Water Applications of Compound A Acid and Haloxyfopmethyl Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.

Compound A Acid	Haloxyfopmethyl	Visual Weed Control (%) - 20 DAA
		SCPJU
gae/ha	gai/ha	Obs	Exp
8.75	0	70
17.5	0	95
35	0	95
0	13.5	0
0	27	0
8.75	13.5	90	70
17.5	13.5	95	95
35	13.5	95	95
8.75	27	95	70
17.5	27	100	95
35	27	100	95

Table 29. Synergistic Activity of In-Water Applications of Compound A Benzyl Ester and Haloxyfop-methyl Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems

Compound A Benzyl Ester	Haloxyfopmethyl	Visual Weed Control (%) - 20 DAA
		CYPRO
gae/ha	gai/ha	Obs	Exp
4.38	0	50
8.75	0	100
17.5	0	100
0	13.5	0
0	27	0
4.38	13.5	75	50
8.75	13.5	95	100
17.5	13.5	100	100
4.38	27	80	50
8.75	27	95	100
17.5	27	100	100

Table 30. Synergistic Activity of In-Water Applications of Compound A Acid and Metamifop Herbicidal Compositions on Weed Control in a Rice Cropping System.

Compound A Acid	Metamifop	Visual Weed Control (%) - 21 DAA
		FIMMI	SCPMA
gae/ha	gai/ha	Obs	Exp	Obs	Exp
35	0	85	-	0	-
0	75	0	-	0	-
0	150	0	-	0	-
35	75	100	85	60	0
35	150	100	85	50	0

Table 31. Synergistic Activity of In-Water Applications of Compound A Benzyl Ester and Metamifop Herbicidal Compositions on Weed Control in a Rice Cropping System.

Compound A Benzyl Ester	Metamifop	Visual Weed Control (%) - 21 DAA
		SCPJU
gae/ha	gai/ha	Obs	Exp
4.38	0	70	-

0	75	0	-
0	150	0	-
4.38	75	99	70
4.38	150	100	70

Compound A Benzyl Ester	Metamifop	Visual Weed Control (%) - 21 DAA
		ECHOR
gae/ha	gai/ha	Obs	Exp
48	0	78	-
96	0	80	-
0	50	20	-
48	50	75	82
96	50	100	84

Table 32. Synergistic Activity of In-Water Applications of Compound A Acid and Fluazifop-pbutyl Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.

Compound A Acid	Fluazifop-Pbutyl	Visual Weed Control (%) - 21 DAA
		ECHOR
gae/ha	gae/ha	Obs	Exp
8.75	0	10	-
17.5	0	15	-
35	0	20	-
0	90	25	-
8.75	90	45	33
17.5	90	15	36
35	90	100	40

Compound A Acid	Fluazifop-Pbutyl	Visual Weed Control (%) - 21 DAA
		CYPRO
gae/ha	gae/ha	Obs	Exp
8.75	0	0
17.5	0	30
35	0	85
0	90	0
0	180	0
8.75	90	70	0
17.5	90	30	30

35	90	95	85
8,75	180	20	0
17.5	180	20	30
35	180	90	85

Table 33. Synergistic Activity of In-Water Applications of Compound A Benzyl Ester and Fluazifop-p-butyl Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.

Compound A Benzyl Ester	FluazifopP-butyl	Visual Weed Control (%) - 21 DAA
		ECHOR
gae/ha	gai/ha	Obs	Exp
8	0	8	-
16	0	5	-
32	0	13	-
0	45	0	-
8	45	0	8
16	45	15	5
32	45	30	13

Table 34. Synergistic Activity of In-Water Applications of Compound A Acid and Quizalofop-pethyl Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.

Compound A Acid	Quizalofopp-ethyl	Visual Weed Control (%) - 21 DAA
		ECHOR
gae/ha	gai/ha	Obs	Exp
17.5	0	25	-
35	0	30	-
0	15	0	-
0	30	60	-
17.5	15	50	25
35	15	50	30
17.5	30	60	70
35	30	100	72

Compound A Acid	Quizalofopp-ethyl	Visual Weed Control (%) - 21 DAA
		CYPRO
gae/ha	gai/ha	Obs	Exp

8.75	0	0	-
0	15	0	- .
0	30	0	-
8.75	15	20	0
8.75	30	20	0

Table 35. Synergistic Activity of In-Water Applications of Compound A Benzyl Ester and Quizalofop-p-ethyl Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.

Compound A Benzyl Ester	Quizalofopp-ethyl	Visual Weed Control (%) - 21 DAA
		ECHCG	ECHOR
gae/ha	gai/ha	Obs	Exp	Obs	Exp
4.38	0	15		0
8.75	0	20		15
17.5	0	75		10
0	15	50		0
0	30	100		60
4.38	15	100	58	60	0
8.75	15	100	60	30	15
17.5	15	100	88	50	10
4.38	30	100	100	100	60
8.75	30	100	100	100	66
17.5	30	100	100	100	64

Table 36. Synergistic Activity of In-Water Applications of Compound A Acid and Profoxydim Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.

Compound A Acid	Profoxydim	Visual Weed Control (%) - 21 DAA
		LEFCH
gae/ha	gai/ha	Obs	Exp
17.5	0	0	-
35	0	20	-
0	25	85	-
17.5	25	100	85
35	25	100	88

Compound A Acid

Visual Weed

Profoxydim Control (%) - 22 DAA

		ECHCG
gae/ha	gai/ha	Obs	Exp
16	0	20	-
32	0	25	-
0	50	30	-
16	50	70	44
32	50	100	48

Compound A Acid	Profoxydim	Visual Weed Control (%) - 22 DAA
		SCPJU
gae/ha	gai/ha	Obs	Exp
16	0	70	-
0	50	0	-
0	100	0	-
16	50	95	70
16	100	100	70

Table 37. Synergistic Activity of In-Water Applications of Compound A Benzyl Ester and Profoxydim Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.

Compound A Benzyl Ester	Profoxydim	Visual Weed Control (%) - 21 DAA
		ECHOR
gae/ha	gai/ha	Obs	Exp
4.38	0	0	-
8.75	0	15	-
17.5	0	10	-
0	25	0	-
4.38	25	30	0
8.75	25	100	15
17.5	25	100	10

Compound A Benzyl Ester	Profoxydim	Visual Weed Control (%) - 22 DAA
		ECHCG
gae/ha	gai/ha	Obs	Exp
8	0	50	-
16	0	60	-
32	0	99	-
0	50	30	-
8	50	100	65

16	50	100	72
32	50	100	99

Table 38. Synergistic Activity of In-Water Applications of Compound A Acid and Sethoxydim Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.

Compound A Acid	Sethoxydim	Visual Weed Control (%) - 21 DAA
		FIMMI
gae/ha	gai/ha	Obs	Exp
8.75	0	20
0	135	50	-
0	270	30	-
8.75	135	100	60
8.75	270	100	44

Compound A Acid	Sethoxydim	Visual Weed Control (%) 21DAA
		SCPJU
gae/ha	gai/ha	Obs	Exp
8.75	0	65	-
17.5	0	90	-
0	135	0	-
8.75	135	95	65
17.5	135	100	90

Table 39. Synergistic Activity of In-Water Applications of Compound A Benzyl Ester and Sethoxydim Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.

Compound A Benzyl Ester	Sethoxydim	Visual Weed Control (%) - 21 DAA
		ECHCG
gae/ha	gai/ha	Obs	Exp
4.38	0	15	-
8.75	0	60	-
0	135	60	-
4.38	135	75	66
8.75	135	100	84

CYPRO Cyperus rotundus L.

ECHCG Echinochloa crusgalli (L.) Beauv.

ECHOR Echinochloa oryzoides (Ard.) Fritsch nutsedge, purple bamyardgrass watergrass, early

FIMMI	Fimbristylis miliacea (L.) Vahl	fringerush, globe
LEFCH	• Leptochloa chinensis (L.) Nees	sprangletop, Chinese
SCPJU	Schoenoplectus juncoides (Roxb.) Palla	bulrush, Japanese
SCPMA	Bolboschoenus maritimus (L.) Palla or
	Schoenoplectus maritimus (L.) Lye	clubrush, sea

gae/ha = grams acid équivalent per hectare gai/ha = grams active ingrédient per hectare Obs = observed value

Example III. Evaluation of Postemergence Foliar-Applied Herbicidal Mixtures for Control of Weeds Common to Row Crops such as Com and Soybeans

Seeds or nutlets of the desired test plant species were planted in a soil matrix prepared by mixing a loam or sandy loam soil (e.g., 28.6 percent silt, 18.8 percent clay, and 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 80 to 20 ratio. The soil matrix was contained in plastic pots with a surface area of 84.6 square centimeters (cm²) and a volume of 560 cubic centimeters (cm³). When required to ensure good germination and healthy plants, a fungicide treatment and/or other chemical or physical treatment was applied. The plants were grown for 7-31 days (d) in a greenhouse with an approximate 15 hour (h) photoperiod which was maintained at about 23-29 °C during the day and 22-28 °C during the night. Nutrients (Peters Excel® 15-5-15 5-Ca 2-Mg) and water were added on a regular basis and supplémentai lighting was provided with overhead métal halide 1000-Watt lamps as necessary. The plants were employed for testing when they reached the first, second, or third true leaf stage.

Forms of compound A (compound of formula I) tested include:

Compound A Acid nh₂

Compound A Benzyl Ester

Other herbicidal components were applied on an acid équivalent basis and included acetyl coA carboxylase (ACCase)-inhibiting herbicide (cyclohexanedione and aryloxyphenoxypropionate chemical classes) quizalofop-p-ethyl formulated as Assure® II.

For treatments comprised of formulated compounds, measured amounts of compounds were placed individually in 25 mL glass vials and diluted in a volume of 1.5% (v/v) Agri-Dex® crop oil concentrated to obtain 6X stock solutions. If a test compound did not dissolve readily, the mixture was warmed and/or sonicated. Application solutions were prepared by adding an appropriate amount of each stock solution (typically 2 mL) and diluted to the appropriate final concentrations with the addition of an appropriate amount of 1.5% (v/v) crop oil concentrate and an appropriate amount of water so that the final spray solutions contained 1.25+/-0.05% (v/v) crop oil concentrate.

For treatments comprised of technical compounds, weighed amounts can be placed individually in 25 mL glass vials and dissolved in a volume of 97:3 v/v acetone/DMSO 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 appropriate amount of each stock solution (e.g., 1 mL) and diluted to the appropriate final concentrations with the addition of an appropriate amount of 1.5% (v/v) crop oil concentrate and an appropriate amount of water so that the final spray solutions contain 1.25% (v/v) crop oil concentrate. When technical materials are used, the concentrated stock solutions can be added to the spray solutions so that the final acetone and DMSO concentrations of the application solutions are 16.2% and 0.5%, respectively.

For treatments comprised of formulated and technical compounds, weighed amounts of the technical materials can be placed individually in 25 mL glass vials and dissolved in a volume of 97:3 v/v acetone/DMSO to obtain 6X stock solutions, and measured amounts of the formulated compounds 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 6X 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 appropriate amount of each stock solution (e.g., 2 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 contained 1.25% (v/v) crop oil concentrate. When required, additional water and/or 97:3 v/v acetone/DMSO can be added to individual application solutions so that the final acetone and DMSO concentrations of the application solutions being compared are 16.2% and 0.5%, respectively.

Ail stock solutions and applications solutions were visually inspected for compound compatibility prior to application. Compound requirements are based upon a 12 mL application volume at a rate of 187 liters per hectare (L/ha). Formulated compounds were applied to the plant material with an overhead Mandel track sprayer equipped with 8002E nozzles calibrated to deliver 187 L/ha over an application area of0.503 square meters (m²) at a spray height of 18 to 20 inches (46 to 50 cm) above the average plant canopy height. Controi plants were sprayed in the same manner with the solvent blank.

The treated plants and controi plants were placed in a greenhouse as described above and watered by sub-irrigation to prevent wash-off of the test compounds. After approximately 2 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 complété kill.

Expected = A + B - (A x B/100)

Some of the compounds tested, application rates employed, plant species tested, and results are given in Tables 40-41.

Table 40. Synergistic Activity of Foliar-Applied Compound A Acid and Quizalofop-p-ethyl Herbicidal Compositions on Control of Weeds Common to Row Crops Such as Com and Soybean Cropping Systems.

Compound A Acid	Quizalofopp-ethyl	Visual Weed Control (%) -14 DAA
		AVEFA
gae/ha	gae/ha	Obs	Exp
3.75	0	0	-
7.5	0	0	-
15	0	0	-
0	14.25	40	-
3.75	14.25	85	40
7.5	14.25	70	40
15	14.25	55	40

Compound A Acid	Quizalofopp-ethyl	Visual Weed Control (%) -14 DAA
		LOLMU
gae/ha	gae/ha	Obs	Exp
3.75	0	0	-
7.5	0	10	-
15	0	10	-
0	3.56	0	-
0	7.125	60	-
3.75	3.56	50	0
7.5	3.56	30	10
15	3.56	40	10
3.75	7.125	70	60
7.5	7.125	80	64
15	7.125	70	64

Table 41. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Quizalofop-p ethyl Herbicidal Compositions on Weeds Common to Row Crops Such as Com and Soybean 15 Cropping Systems.

Compound A Benzyl Ester	Quizalofopp-ethyl	Visual Weed Control (%) -14 DAA
		AVEFA
gae/ha	gae/ha	Obs	Exp
3.75	0	10	-
7.5	0	0	-
15	0	10	-
0	14.25	40	-
3.75	14.25	75	46
7.5	14.25	99	40
15	14.25	40	46

Compound A Benzyl Ester	Quizalofopp-ethyl	Visual Weed Control (%) -14 DAA
		LOLMU
gae/ha	gae/ha	Obs	Exp
3.75	0	0
7.5	0	10
15	0	10
0	3.56	0
0	7.125	60
3.75	3.56	60	0
7.5	3.56	40	10
15	3.56	35	10
3.75	7.125	70	60
7.5	7.125	75	64
15	7.125	80	64

AVEFA Avena fatua L. oat, wild

LOLMU Lolium midtiflorum Lam. ryegrass, Italian gae/ha = grams acid équivalent per hectare gai/ha = grams active ingrédient per hectare

Obs = observed value

Exp = expected value as calculated by Colby’s équation

DAA = days after application

Example IV. Evaluation of Postemergence Herbicidal Activity of Mixtures in Cereal Crops in the Greenhouse.

Seeds of the desired test plant species were planted in Sun Gro MetroMix® 306 planting mixture, which typically has a pH of 6.0 to 6.8 and an organic matter content of about 30 percent, in plastic pots with a surface area of 103.2 square centimeters (cm²). When required to ensure good germination and healthy plants, a fongicide treatment and/or other chemical or physical treatment was applied. The plants were grown for 7-36 days in a greenhouse with an approximate 14 hour photoperiod which was maintained at about 18° C during the day and about 17° C during the night. Nutrients and water were added on a regular basis and supplémentai lighting was provided with overhead métal halide 1000-Watt lamps as necessary. The plants were empioyed for testing when they reached the second or third true leaf stage.

Treatments consisted of the benzyl ester of 4-amino-3-chloro-5-fluoro-6-(4-chloro-2fluoro-3-methoxy-phenyl)pyridine-2-carboxylic acid (Compound A), formulated as an SC, a second cereal herbicide alone and then both in combination.

Forms of compound A (compound of formula I) tested include:

Compound A Benzyl Ester

Other herbicidal components were applied on an active ingrédient basis and included acetyl-CoA carboxylase (ACCase)-inhibiting herbicides clodinafop-propargyl, fenoxaprop-Pethyl, pinoxaden and tralkoxydim.

Measured aliquots of benzyl ester of 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3methoxy-phenyl)pyridine-2-carboxylic acid (Compound A) were placed in 25 milliliter (mL) glass vials and diluted in a volume of 1.25% (v/v) Agri-Dex® crop oil concentrate to obtain stock solutions. Compound requirements are based upon a 12 mL application volume at a rate of 187 liters per hectare (L/ha). Spray solutions of the second cereal herbicide and experimental compound mixtures were prepared by adding the stock solutions to the appropriate amount of dilution solution to form 12 mL spray solution with active ingrédients in two- and three-way combinations. Formulated compounds were applied to the plant material with an overhead Mandel track sprayer equipped with an 8002E nozzle calibrated to deliver 187 L/ha over an application area of 0.503 square meters (m²) at a spray height of 18 inches (46 cm) above average plant canopy. Control plants were sprayed in the same manner with the solvent blank.

The treated plants and control plants were placed in a greenhouse as described above and watered by sub-irrigation to prevent wash-off of the test compounds. After 20-22 days, the condition of the test plants as compared with that of the control plants was determined visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury and 100 corresponds to complété kill.

Colby’s équation was used to détermine the herbicidal effects expected from the mixtures 5 (Colby, S.R. 1967. Calculation ofthe synergistic and antagoniste response ofherbicide combinations. Weeds 15:20-22.).

Expected = A + B - (A x B/100)

The compounds tested, application rates employed, plant species tested, and results are given in 15 Tables 42-45.

Table 42. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Clodinafoppropargyl Herbicidal Compositions on Weed Control in a Cereals Cropping System.

Compound A Benzyl Ester	Clodinofoppropargyl	Visual Weed Control (%) - 21 DAA
		LOLMU	KCHSC
gai/ha	gai/ha	Obs	Exp	Obs	Exp
5	0	0	-	20	-
10	0	0	-	30	-
0	15	60	-	0	-
0	30	48	-	10	-
5	15	60	60	70	20
10	15	65	60	80	30
5	30	73	48	70	28
10	30	78	48	80	37

Compound A Benzyl Ester	Clodinofoppropargyl	Visual Weed Control (%) - 21 DAA
		PHAMI	APESV	ALOMY
gai/ha	gai/ha	Obs	Exp	Obs	Exp	Obs	Exp
5	0	0	-	0	-	0	-
10	0	0	-	0	-	0	-
0	15	48	-	15	-	80	-

0	30	55	-	68	-	82	-
5	15	73	48	55	15	90	80
10	15	73	48	55	15	88	80
5	30	55	55	78	68	94	82
10	30	45	55	80	68	87	82

Table 43. Synergistic Activity ofFoliar-Applied Compound A Benzyl Ester and Fenoxaprop-Pethyl Herbicidal Compositions on Weed Control in a Cereals Cropping System.

Compound A Benzyl Ester	FenoxapropP-ethyl	Visual Weed Control (%) - 21 DAA
		KCHSC	PHAMI	APESV
gai/ha	gai/ha	Obs	Exp	Obs	Exp	Obs	Exp
5	0	20	-	0	-	0	-
10	0 .	30	-	0	-	0	-
0	23	0	-	10	-	50	-
0	46	0	-	45	-	83	-
5	23	60	20	10	10	65	50
10	23	68	30	10	10	63	50
5	46	70	20	55	45	81	83
10	46	70	30	55	45	83	83

Table 44. Synergistic Activity ofFoliar-Applied Compound A Benzyl Ester and Pinoxaden Herbicidal Compositions on Weed Control in a Cereals Cropping System.

Compound A Benzyl Ester	Pinoxaden	Visual Weed Control (%) - 21 DAA
		KCHSC	PHAMI
gai/ha	gai/ha	Obs	Exp	Obs	Exp
5	0	20	-	0	-
10	0	30	-	0	-
0	15	0	-	78	-
0	30	15	-	94	-
5	15	75	20	88	78
10	15	75	30	87	78
5	30	75	32	94	94
10	30	78	41	94	94

Table 45. Synergistic Activity ofFoliar-Applied Compound A Benzyl Ester and Tralkoxydim Herbicidal Compositions on Weed Control in a Cereals Cropping System.

Compound A Benzyl Ester	Tralkoxydim	Visual Weed Control (%) - 21 DAA
		AVEFA	LOLMU	KCHSC
gai/ha	gai/ha	Obs ·	Exp	Obs	Exp	Obs	Exp
5	0	0	-	0	-	20	-
10	0	0	-	0	-	30	-
0	50	78	-	86	-	10	-
0	100	99	-	96	-	0	-
5	50	95	78	95	86	55	28
10	50	96	78	94	86	65	37
5	100	97	99	97	96	65	20
10	100	97	99	95	96	73	30

ALOMY	Alopecurus myosuroides Huds.	blackgrass
APESV	Apera spica-venti (L.) Beauv.	windgrass
AVEFA	Avena fatua L.	wild oat
KCHSC	Kochia scoparia (L.) Schrad.	kochia
LOLMU	Lolium multiflorum Lam.	ryegrass, Italian

PHAMI Phalaris minor Retz.

Canarygrass, littleseed gae/ha = grams acid équivalent per hectare gai/ha = grams active ingrédient per hectare

Obs = observed value

Exp = expected value as calculated by Colby’s équation

DAA = days after application

Example V. Evaluation of Post-emergence Herbicidal Activity of Mixtures Applied Under Field Conditions to Seeded Rice

Multiple field trials were conducted under commercial grower field conditions in Tolima, Colombia; Thessaloniki, Greece; Bianze and Copiano, Italy; and Humphrey, Arkansas, USA. Trials sites were located in commercially grown fïelds of direct-seeded rice (Oryza sativa) using standard herbicide small plot research methodology. Plots varied from 2 to 3 meter (m) x 5 to 8 m (width x length) with 4 replicates per treatment. The rice crop was grown using normal cultural practices for fertilization, seeding, watering, flooding and maintenance to ensure good growth of the crop and the weeds.

Ail treatments in the field trials were applied using a backpack compressed air/gas sprayer with fiat fan nozzles (80° or 110°) calibrated to apply 187 to 300 L/ha spray volume at approximately 200-400 kPa nozzle pressure. Commercially available products of cyhalofopbutyl (Clincher 180EC, Clincher 200EC, and Clincher SF (285 gr ai/L EC)) were mixed in water at appropriate formulated product rates to achieve the desired rates based on a unit area of application (hectare) to achieve the desired rates as shown. Treatments were rate at 19 to 58 days after application (DAA) as compared to the untreated control plants. Visual weed control was scored on a scale of 0 to 100 percent where 0 corresponds to no injury and 100 corresponds to complété kill.

Ail treatment results, both for the single product and mixtures, are an average of 4 replicates. The trial sites had naturally occurring populations of weeds. The weed spectrum included, but was not limited to, rice flatsedge (Cyperus iria, CYPIR); smallflower umbrellaplant (Cyperus difformis, CYPDI), junglerice (Echinochloa colona, ECHCO), bamyardgrass (Echinochloa crus-galli, ECHCG); multiple Echinochloa species in the same field (ECHSS), grasslike fimbristylis (Fimbristylis miliacea, FIMMI); ricefield bulrush (Schoenoplectus mucronatus, SCPMU) and hemp Sesbania (Sesbania exaltata, SEBEX). Ail synergistic interactions were significant at the P>0.01 Ievel.

Some of the compounds tested, application rates employed, plant species tested, and results are given in Tables 46-48.

Table 46. Synergistic Activity ofFoliar-Applied Compound A Benzyl Ester and Cyhalofop-butyl

Herbicidal Compositions on Weed Control in a Rice Cropping System when evaluated 19 DAA (Days After Application) in Tolima, Colombia.

Compound A Benzyl Ester	Cyhalofopbutyl	Visual Weed Control (%) -19 DAA
		CYPIR	ECHCO	FIMMI
gae/ha	gai/ha	Obs	Exp	Obs	Exp	Obs	Exp
12	0	69	-	76	-	-	-
0	280	0	-	0	-	-	-
12	280	85	69	90	76	-	-
24	0	-	-	-	-	39	-
0	190	-	-	-	-	16	-
24	190	-	-	-	-	63	48

Table 47. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Cyhalofopbutyl Herbicidal Compositions on Weed Control in a Rice Cropping System when evaluated 7DAA (Days After Application) in Humphrey, Arkansas, USA.

Compound A Benzyl Ester	Cyhalofopbutyl	Visual Weed Control (%) - 7 DAA
		SEBEX
gae/ha	gai/ha	Obs	Exp
24	0	80	-
0	280	0	-
24	280	90	80
32	0	78	-
0	280	0	-
32	280	93	78

Table 48. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Cyhalofopbutyl Herbicidal Compositions on Weed Control in a Rice Cropping System when evaluated 55 10 to 58 DAA (Days After Application) in Greece (CYPDI and ECHCG) and Italy (ECHSS and

SCPMU).

Compound A Benzyl Ester	Cyhalofopbutyl	Visual Weed Control (%) - 55-58 DAA
		CYPDI	ECHCG	ECHSS	SCPMU


gae/ha	gai/ha	Obs	Exp	Obs	Exp	Obs	Exp	Obs	Exp
24	0	81	-	6	-	40	-	27	-
0	300	0	-	29	-	37	-	6	-
24	300	90	81	60	33	89	62	56	27

Example V. Evaluation of Postemergence Foliar-Applied Temary Herbicidal Mixtures for Weed Control in Direct Seeded Rice

Seeds or nutlets of the desired test plant species 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 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 ratio. The soil matrix was contained in plastic pots with a volume of 1 quart and a surface area of 83.6 square centimeters (cm²). When required to ensure good germination and healthy plants, a fongicide treatment and/or other chemical or physical treatment was applied. The plants were grown for 8-22 days in a greenhouse with an approximate 14 hr. photoperiod which was maintained at about 29° C during the day and 26° C during the night. Nutrients (Peters Excel® 15-5-15 5-Ca 2-Mg and iron chelate) were applied in the irrigation solution as needed and water was added on a regular basis. Supplémentai lighting was provided with overhead métal halide 1000-Watt lamps as necessary. The plants were employed for testing when they reached the first through fourth true leaf stage.

Treatments consisted of the benzyl ester of 4-amino-3-chloro-5-fluoro-6-(4-chloro-2fluoro-3-methoxy-phenyl)pyridine-2-carboxylic acid (Compound A), formulated as an SC (suspension concentrate), an ACCase inhibitor, and a third herbicidal component, each applied alone and in temary combination. Forms of compound A were applied on an acid équivalent basis.

Forms of compound A (compound of formula I) tested include:

Compound A Benzyl Ester

The ACCase inhibitor component was applied on an active ingrédient basis and included cyhalofop-R-butyl formulated as Clincher® SF, fenoxaprop-p-ethyl formulated as RiceStar® HT, and profoxydim formulated as Aura® 20EC. Other herbicidal components were applied on an active ingrédient or acid équivalent basis depending on the compound and included penoxsulam formulated as Grasp® SC, bentazon sodium formulated as Basagran®, triclopyr trimethylammonium (TEA) sait formulated as Grandstand® R, bispyribac sodium formulated as Régiment® 80WP, imazamox ammonium formulated as Beyond®, benzobicyclon, quinclorac formulated as Facet® 75DF, glyphosate dimethylammonium (DMA) sait formulated as Durango® DMA, glufosinate ammonium formulated as Ignite® 280, fentrazamide formulated as an emsulsifiable concentrate (EC), propyrisulfuron formulated as Zêta One®, and indanofan (technical grade material).

For treatments comprised of formulated compounds, measured amounts of compounds were piaced individually in 25 mL glass vials and diluted in a volume of 1.25% (v/v) Agri-Dex® crop oil concentrate to obtain 12X stock solutions. If a test compound did not dissolve readily, the mixture was warmed and/or sonicated. Application solutions were prepared by adding an appropriate amount of each stock solution (e.g., 1 mL) and diluted to the appropriate final concentrations with the addition of 9 mL of an aqueous mixture of 1.25% (v/v) crop oil concentrate so that the final spray solutions contained 1.25% (v/v) crop oil concentrate.

For treatments comprised of formulated and technical compounds, weighed amounts of the technical materials were piaced individually in 25 mL glass vials and dissolved in a volume of 97:3 v/v acetone/DMSO to obtain 12X stock solutions, and measured amounts of the formulated compounds were piaced 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 dissolve readily, the mixture was warmed and/or sonicated. Application solutions were prepared by adding an appropriate 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 contained 1.25% (v/v) crop oil concentrate. As required, additional water and/or 97:3 v/v acetone/DMSO was added to individual application solutions so that the final acetone and DMSO concentrations of the application solutions being compared were 8.1% and 0.25%, respectively.

Ail stock solutions and applications solutions were visually inspected for compound compatibility prior to application. Spray solutions were applied to the plant material with an overhead Mandel track sprayer equipped with a 8002E nozzles calibrated to deliver 187 L/ha

100 over an application area of 0.503 m² at a spray height of 18 inches (46 cm) above average plant canopy height. Control plants were sprayed in the same manner with the solvent blank.

The following équation was used to calculate the expected activity of mixtures containing three active ingrédients, A, B, and C:

Expected = A + B + C-((A x B + A x C + B x C)/100) + (A x B x C/10000)

C = observed efficacy of active ingrédient C at the same concentration as used in the mixture.

The compounds tested, application rates employed, plant species tested, and results are given in Tables 49-62.

Table 49. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester, Cyhalofop-Butyl, and Penoxsulam Temary Herbicidal Compositions on Weed Control in a Rice Cropping System.

Compound A Benzyl Ester	Cyhalofopbutyl	Penoxsulam	Visual Weed Control (%) - 21 DAA
			IPOHE
gae/ha	gai/ha	gai/ha	Obs	Exp
8	0	0	15	-
16	0	0	33	-
0	35	0	0	-
0	0	8.75	48	-
8	35	8.75	62	56
16	35	8.75	90	66

101

Table 50. Synergistic Activity ofFoliar-Applied Compound A Benzyl Ester, Cyhalofop-Butyl, and Bentazon Temary Herbicidal Compositions on Weed Control in a Rice Cropping System.

Compound A Benzyl Ester	Cyhalofopbutyl	Bentazon sodium	Visual Weed Control (%) - 21 DAA
			IPOHE
gae/ha	gai/ha	gae/ha	Obs	Exp
2.19	0	0	30	-
4.38	0	0	38	-
0	35	0	0	-
0	0	420	53	-
2.19	35	420	70	67
4.38	35	420	82	71

Compound A Benzyl Ester	Cyhalofopbutyl	Bentazon sodium	Visual Weed Control (%) - 21 DAA
			IPOHE
gae/ha	gai/ha	gae/ha	Obs	Exp
8	0	0	15	-
16	0	0	33	-
0	35	0	0	-
0	0	420	75	-
8	35	420	85	79
16	35	420	93	83

Table 51. Synergistic Activity ofFoliar-Applied Compound A Benzyl Ester, Cyhalofop-Butyl, and Triclopyr TEA Sait Temary Herbicidal Compositions on Weed Control in a Rice Cropping System.

Compound A Benzyl Ester	Cyhalofop - butyl	Triclopyr TEA Sait	Visual Weed Control (%) - 21 DAA
			ECHCG	ECHCO	SCPJU
gae/ha	gai/ha	gae/ha	Obs	Exp	Obs	Exp	Obs	Exp
2.19	0	0	5	-	10	-	65	-
4.38	0	0	27	-	25	-	96	-
0	35	0	20	-	37	-	0	-
0	0	17.5	0	-	3	-	43	-
2.19	35	17.5	35	24	45	45	98	80
4.38	35	17.5	37	41	90	54	100	98

102

Compound A Benzyl Ester	Cyhalofopbutyl	Triclopyr TEA Sait	Visual Weed Control (%) - 21 DAA
			CYP IR
gae/ha	gai/ha	gae/ha	Obs	Exp
8	0	0	53	-
16	0	0	95	-
0	35	0	0	-
0	0	17.5	0	-
8	35	17.5	100	53
16	35	17.5	100	95

Table 52. Synergistic Activity ofFoliar-Applied Compound A Benzyl Ester, Cyhalofop-Butyl, and Bispyribac Sodium Temary Herbicidal Compositions on Weed Control in a Rice Cropping System.

Compound A Benzyl Ester	Cyhalofopbutyl	Bispyribac sodium	Visual Weed Control (%) - 21 DAA
			IPOHE	CYPES
gae/ha	gai/ha	gai/ha	Obs	Exp	Obs	Exp
8	0	0	10	-	70	-
0	35	0	0	-	0	-
0	0	28	60	-	20	-
8	35	28	83	64	90	76

Table 53. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester, Cyhalofop-Butyl, and Imazamox Ammonium Temary Herbicidal Compositions on Weed Control in a Rice Cropping System.

Compound A Benzyl Ester	Cyhalofopbutyl	Imazamox ammonium	Visual Weed Control (%) - 21 DAA
			CYPES
gae/ha	gai/ha	gai/ha	Obs	Exp
8	0	0	70
0	35	0	0
0	0	12	60
8	35	12	95	88

Compound A Benzyl Ester

Cyhalofopbutyl

Imazamox ammonium

Visual Weed Control (%) - 21 DAA

103

			IPOHE
gae/ha	gai/ha	gae/ha	Obs	Exp
8	0	0	20	-
0	17.5	0	0	-
0	0	6	65	-
8	17.5	6	85	72

Table 54. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester, Cyhalofop-Butyl, and Benzobicyclon Temary Herbicidal Compositions on Weed Control in a Rice Cropping System.

Compound A Benzyl Ester	Cyhalofopbutyl	Benzobicyclon	Visual Weed Control (%) - 21 DAA
			ECHCG
gae/ha	gai/ha	gai/ha	Obs	Exp
8	0	0	38	-
0	35	0	20	-
0	0	200	0	-
8	35	200	90	50

Compound A Benzyl Ester	Cyhalofopbutyl	Benzobicyclon	Visual Weed Control (%) - 21 DAA
			IPOHE
gae/ha	gai/ha	gai/ha	Obs	Exp
8	0	0	10	-
16	0	0	30	-
0	35	0	0	-
0	0	200	55	-
8	35	200	78	60
16	35	200	85	69

Table 55. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester, Cyhalofop-Butyl, and Quinclorac Temary Herbicidal Compositions on Weed Control in a Rice Cropping System.

Compound A Benzyl Ester	Cyhalofopbutyl	Quinclorac	Visual Weed Control (%) - 21 DAA
			ECHCG	CYPES
gae/ha	gai/ha	gai/ha	Obs	Exp	Obs	Exp
8	0	0	38	-	70	-
0	35	0	20	-	0	-

104

0	0	280	10	-	0	-
8	35	280	92	55	85	70

Table 56. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester, Cyhalofop-Butyl, and Glyphosate Dimethylammonium (DMA) Sait Temary Herbicidal Compositions on Weed Control in a Rice Cropping System.

Compound A Benzyl Ester	Cyhalofopbutyl	Glyphosate DMA	Visual Weed Control (%) - 21 DAA
			LEFCH
gae/ha	gai/ha	gai/ha	Obs	Exp
16	0	0	25	-
0	35	0	68	-
0	0	420	45	-
16	35	420	93	87

Compound A Benzyl Ester	Cyhalofopbutyl	Glyphosate DMA	Visual Weed Control (%) - 21 DAA
			ECHCG
gae/ha	gai/ha	gae/ha	Obs	Exp
8	0	0	45	-
0	17.5	0	33	-
0	0	105	23	-
8	17.5	105	83	71

Table 57. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester, Cyhalofop-Butyl, and Glufosinate Ammonium Temary Herbicidal Compositions on Weed Control in a Rice Cropping System.

Compound A Benzyl Ester	Cyhalofopbutyl	Glufosinate ammonium	Visual Weed Control (%) - 21 DAA
			ECHCO
gae/ha	gai/ha	gai/ha	Obs	Exp
8	0	0	45	-
0	35	0	40	-
0	0	115	0	-
8	35	115	80	67

105

Table 58. Synergistic Activity ofFoliar-Appiied Compound A Benzyl Ester, Cyhalofop-Butyl, and Fentrazamide Temary Herbicidal Compositions on Weed Control in a Rice Cropping System.

Compound A Benzyl Ester	Cyhalofopbutyl	Fentrazamide	Visual Weed Control (%) - 22 DAA
			ECHCG	ECHOR
gae/ha	gai/ha	gai/ha	Obs	Exp	Obs	Exp
8	0	0	40		13
16	0	0	58		40
0	17.5	0	0		0
0	35	0	12		15
0	0	33.75	0		3
0	0	67.5	0		0
8	17.5	33.75	40	40	25	16
8	17.5	67.5	67	40	52	13
8	35	33.75	48	47	63	29
8	35	67.5	65	47	55	26
16	17.5	33.75	83	58	60	42
16	17.5	67.5	80	58	82	40
16	35	33.75	92	63	80	51
16	35	67.5	87	63	87	49

Table 59. Synergistic Activity ofFoliar-Appiied Compound A Benzyl Ester, Cyhalofop-Butyl, and Propyrisulfuron Temary Herbicidal Compositions on Weed Control in a Rice Cropping System.

Compound A Benzyl Ester	Cyhalofopbutyl	Propyrisulfuron	Visual Weed Control (%) 22 DAA
			ECHOR
gae/ha	gai/ha	gai/ha	Obs	Exp
8	0	0	13	-
0	35	0	15	-
0	0	22.5	55	-
8	35	22.5	78	67

Table 60. Synergistic Activity of Foliar-Appiied Compound A Benzyl Ester, Fenoxaprop-pEthyl + Isoxadifen-ethyl, and Penoxsulam Temary Herbicidal Compositions on Weed Control in a Rice Cropping System.

106

Compound A Benzyl Ester	Penoxsulam	Fenoxapropp-ethyl + Isoxadifenethyl	Visual Weed Control (%) - 22 DAA
			ECHOR
gae/ha	gai/ha	gai/ha	Obs	Exp
8	0	0	25
16	0	0	35
0	4.38	0	45
0	8.75	0	53
0	0	4.38	0
8	4.38	4.38	73	59
8	8.75	4.38	62	65
16	4.38	4.38	82	64
16	8.75	4.38	87	70

Compound A Benzyl Ester	Penoxsulam	Fenoxapropp-ethyl + Isoxadifenethyl	Visual Weed Control (%) - 22 DAA
			CYPIR
gae/ha	gai/ha	gai/ha	Obs	Exp
8	0	0	37	-
0	4.38	0	50	-
0	0	4.38	0	-
0	0	8.75	0	-
8	4.38	4.38	83	68
8	4.38	8.75	88	68

Table 61. Synergistic Activity ofFoliar-Applied Compound A Benzyl Ester, Profoxydim, and Penoxsulam Temary Herbicidal Compositions on Weed Control in a Rice Cropping System.

Compound A Benzyl Ester	Penoxsulam	Profoxydim	Visual Weed Control (%) - 22 DAA
			ECHOR
gae/ha	gai/ha	gai/ha	Obs	Exp
8	0	0	25	-
16	0	0	35	-
0	4.38	0	45	-
0	0	3.12	0	-
8	4.38	3.12	73	59
16	4.38	3.12	70	64

107

Compound A Benzyl Ester	Penoxsulam	Profoxydim	Visual Weed Control (%) - 22 DAA
			CYPIR
gae/ha	gai/ha	gai/ha	Obs	Exp
8	0	0	37	-
0	4.38	0	50	-
0	0	3.12	0	-
0	0	6.25	0	-
8	4.38	3.12	87	68
8	4.38	6.25	87	68

Table 62. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester, Cyhalofop-butyl, and Indanofan Temary Herbicidal Compositions on Weed Control in a Rice Cropping System.

Compound A Benzyl Ester	Cyhalofopbutyl	Indanofan	Visual Weed Control (%) - 22 DAA
			LEFCH
gae/ha	gai/ha	gai/ha	Obs	Exp
8	0	0	28	-
0	35	0	70	-
0	0	72.5	30	-
0	0	145	38	-
8	35	72.5	95	85
8	35	145	98	86

CYPES

CYP IR

ECHCG

ECHCO

ECHOR

IPOHE

LEFCH

Cyperus esculentus L.

Cyperus iria L.

Echinochloa crusgalli (L.) Beauv.

Echinochloa colona (L.) Link

Echinochloa oryzoides (Ard.) Fritsch Ipomoea hederacea Jacq.

Leptochloa chinensis (L.) Nees

Schoenoplectus juncoides (Roxb.) Palla

SCPJU gae/ha = grams acid équivalent per hectare gai/ha = grams active ingrédient per hectare Obs = observed value nutsedge, yellow flatsedge, rice bamyardgrass junglerice early watergrass momingglory, ivyleaf sprangletop, Chinese bulrush, Japanese

Exp = expected value as calculated by Colby’s équation

DAA = days after application

108

Example VI. Evaluation of In-Water Applied Temary Herbicidal Mixtures for Weed Controi in Transplanted Paddy Rice

Weed seeds or nutlets of the desired test plant species were planted in puddled soil (mud) prepared by mixing a shredded, non-sterilized minerai soil (50.5 percent silt, 25.5 percent clay, and 24 percent sand, with a pH of about 7.6 and an organic matter content of about 2.9 percent) and water at a 1:1 volumétrie ratio. The prepared mud was dispensed in 365 mL aliquots into 16-ounce (oz.) non-perforated plastic pots with a surface area of 86.59 square centimeters (cm²) leaving a headspace of 3 centimeters (cm) in each pot. Mud was allowed to dry ovemight prior to planting or transplanting. Rice seeds were planted in Sun Gro MetroMix® 306 planting mixture, which typically has a pH of 6.0 to 6.8 and an organic matter content of about 30 percent, in plastic plug trays. Seedlings at the second or third leaf stage of growth were transplanted into 860 mL of mud contained in 32-oz. non-perforated plastic pots with a surface area of 86.59 cm² 4 days prior to herbicide application. The paddy was created by filling the headspace of the pots with 2.5 to 3 cm of water. When required to ensure good germination and healthy plants, a fongicide treatment and/or other chemical or physical treatment was applied. The plants were grown for 4-22 days in a greenhouse with an approximate 14 hr. photoperiod which was maintained at about 29°C during the day and 26°C during the night. Nutrients were added as Osmocote® (19:6:12, N:P:K + minor nutrients) at 2 g per 16-oz. pot and 4 g per 32-oz. pot. Water was added on a regular basis to maintain the paddy flood, and supplémentai lighting was provided with overhead métal halide 1000-Watt lamps as necessary. The plants were employed for testing when they reached the first through fourth true leaf stage.

Treatments consisted of the benzyl ester of 4-amino-3-chloro-5-fluoro-6-(4-chloro-2fluoro-3-methoxy-phenyl)pyridine-2-carboxylic acid (Compound A), formulated as an SC (suspension concentrate), an ACCase inhibitor herbicide, and a third herbicidal component, each applied alone and in temary combination. Forms of compound A were applied on an acid équivalent basis.

Forms of compound A (compound of formula I) tested include:

Compound A Benzyl Ester

109

The ACCase inhibitor component was applied on an active ingrédient basis and included cyhalofop-R-butyl formulated as Clincher® G and metamifop formulated as Metamifop EC. Other herbicidal components were applied on an active ingrédient or acid équivalent basis depending on the compound and included penoxsulam formulated as Grasp® SC, bentazon sodium formulated as Basagran®, triclopyr trimethylammonium (TEA) sait formulated as Grandstand® R, benzobicyclon formulated as Benzobicyclon, benfuresate formulated as Full Slot® WG, pyraclonil formulated as Pyraclon® Flowable, mefenacet (technical grade material), and pretilachlor (technical grade material).

Treatment requirements for each compound or herbicidal component were calculated based upon the rates being tested, the concentration of active ingrédient or acid équivalent in the formulation, an application volume of 1 mL per component per pot, and an application area of 86.59 cm² per pot.

For technical grade compounds, a weighed amount was placed in an individual 100 to 200 mL glass vial and was dissolved in a volume of acetone to obtain concentrated stock solutions. If the test compound did not dissolve readily, the mixture was warmed and/or sonicated. The concentrated stock solutions obtained were diluted with an équivalent volume of an aqueous mixture containing 2.5% (v/v) oil concentrate so that the final application solutions contained 1.25% (v/v) crop oil concentrate.

Applications were made by injecting with a pipetter appropriate amounts of the application solutions, into the aqueous layer of the paddy. Control plants were treated in the same manner with the solvent blank. Applications were made so that ail treated plant material received the same concentrations of acetone and crop oil concentrate.

110

Expected = A + B + C-((A xB + AxC + Bx C)/100) + (A x B x C/10000) A = observed efficacy of active ingrédient A at the same concentration as used in the 5 mixture.

The compounds tested, application rates employed, plant species tested, and results are given in Tables 63-71.

Table 63. Synergistic Activity of In-Water Applications of Compound A Benzyl Ester, Cyhalofop-butyl, and Penoxsulam Temary Herbicidal Compositions on Weed Control in a Rice Cropping System.

________________________

Compound A Benzyl Ester	Cyhalofopbutyl	Penoxsulam	Visual Weed Control (%) - 21 DAA
			FIMMI	ECHCG
gae/ha	gai/ha	gai/ha	Obs	Exp	Obs	Exp
1.09	0	0	8		0
2.19	0	0	33		7
0	22.5	0	33		0
0	45	0	0		3
0	0	1.25	33		17
1.09	22.5	1.25	70	59	28	17
2.19	22.5	1.25	95	70	58	22
1.09	45	1.25	65	39	45	19
2.19	45	1.25	87	56	87	25

Compound A Benzyl Ester	Cyhalofopbutyl	Penoxsulam	Visual Weed Control (%) - 21 DAA
			ECHCG
gae/ha	gai/ha	gai/ha	Obs	Exp
4	0	0	25	-
8	0	0	45	-
16	0	0	99	-
0	45	0	30	-
0	0	2.5	55	-
4	45	2.5	85	76

111

8	45	2.5	100	83
16	45	2.5	100	100

Compound A Benzyl Ester	Cyhalofopbutyl	Penoxsulam	Visual Weed Control (%) - 21 DAA
			CYPRO
gae/ha	gai/ha	gai/ha	Obs	Exp
2.19	0	0	0	-
0	22.5	0	0	-
0	45	0	0	-
0	0	1.25	0	-
2.19	22.5	1.25	23	0
2.19	45	1.25	28	0

Compound A Benzyl Ester	Cyhalofopbutyl	Penoxsulam	Visual Weed Control (%) - 24 DAA
			CYPRO
gae/ha	gai/ha	gai/ha	Obs	Exp
4	0	0	40
8	0	0	60
16	0	0	85
0	90	0	0
0	180	0	0
0	. 0	2.5	0
0	0	5	0
4	90	2.5	60	40
8	90	2.5	55	60
16	90	2.5	90	85
4	90	5	68	40
8	90	5	90	60
16	90	5	85	85
4	180	2.5	60	40
8	180	2.5	90	60
16	180	2.5	100	85
4	180	5	50	40
8	180	5	95	60
16	180	5	100	85

Compound A Benzyl Ester	Cyhalofopbutyl	Penoxsulam	Visual Weed Control (%) - 24 DAA
			FIMMI
gae/ha	gai/ha	gai/ha	Obs	Exp
4	0	0	0	-

112

8	0	0	50	-
16	0	0	30	-
0	90	0	0	-
0	180	0	20	-
0	0	2.5	60	-
4	90	2.5	78	60
8	90	2.5	95	80
16	90	2.5	100	72
4	180	2.5	90	68
8	180	2.5	80	84
16	180	2.5	99	78

Compound A Benzyl Ester	Cyhalofopbutyl	Penoxsulam	Visual Weed Control (%) - 24 DAA
			SCPMA
gae/ha	gai/ha	gai/ha	Obs	Exp
4	0	0	0
8	0	0	0
16	0	0	0
0	180	0	0
0	0	5	30
4	180	5	25	30
8	180	5	70	30
16	180	5	80	30

Table 64. Synergistic Activity of In-Water Applications of Compound A Benzyl Ester, Cyhalofop-butyl, and Bentazon Sodium Temary Herbicidal Compositions on Weed Control in a 5 Rice Cropping System.

Compound A Benzyl Ester	Cyhalofopbutyl	Bentazon Sodium	Visual Weed Control (%) - 21 DAA
			ECHCG
gae/ha	gai/ha	gae/ha	Obs	Exp
1.09	0	0	0
2.19	0	0	7
0	22.5	0	0
0	45	0	3
0	0	210	0
1.09	22.5	210	20	0
2.19	22.5	210	17	7
1.09	45	210	13	3
2.19	45	210	72	10

113

Compound A Benzyl Ester	Cyhalofopbutyl	Bentazon Sodium	Visual Weed Control (%) - 21 DAA
			ECHCG
gae/ha	gai/ha	gae/ha	Obs	Exp
4	0	0	25
8	0	0	45
16	0	0	99
0	45	0	30
0	0	420	15
4	45	420	85	55
8	45	420	100	67
16	45	420	100	99

Compound A Benzyl Ester	Cyhalofopbutyl	Bentazon Sodium	Visual Weed Control (%) - 21 DAA
			FIMMI
gae/ha	gai/ha	gae/ha	Obs	Exp
1.09	0	0	8	-
2.19	0	0	33	-
0	45	0	0	-
0	0	210	17	-
1.09	45	210	33	24
2.19	45	210	68	44

Compound A Benzyl Ester	Cyhalofopbutyl	Bentazon Sodium	Visual Weed Control (%) - 21 DAA
			FIMMI
gae/ha	gai/ha	gae/ha	Obs	Exp
4	0	0	62	-
0	22.5	0	0	-
0	45	0	0	-
0	0	420	30	-
4	22.5	420	93	73
4	45	420	100	73

Table 65. Synergistic Activity of In-Water Applications of Compound A Benzyl Ester,

Cyhalofop-butyl, and Triclopyr Trimethylammonium (TEA) Sait Temary Herbicidal Compositions on Weed Control in a Rice Cropping System.

Compound A Benzyl Ester

Cyhalofopbutyl

Triclopyr TEA

Visual Weed Control (%) - 21 DAA

114

			ECHCG
gae/ha	gai/ha	gae/ha	Obs	Exp
1.09	0	0	0
2.19	0	0	7
0	22.5	0	0
0	45	0	3
0	0	17.5	0
1.09	22.5	17.5	25	0
2.19	22.5	17.5	48	7
1.09	45	17.5	37	3
2.19	45	17.5	48	10

Compound A Benzyl Ester	Cyhalofopbutyl	Triclopyr TEA	Visual Weed Control (%) - 21 DAA
			ECHCG
gae/ha	gai/ha	gai/ha	Obs	Exp
4	0	0	25
8	0	0	45
16	0	0	99
0	45	0	30
0	0	35	0
4	45	35	100	48
8	45	35	100	62
16	45	35	95	99

Compound A Benzyl Ester	Cyhalofopbutyl	Triclopyr TEA	Visual Weed Control (%) - 21 DAA
			SCPJU
gae/ha	gai/ha	gae/ha	Obs	Exp
2.19	0	0	77	-
0	22.5	0	0	-
0	45	0	0	-
0	0	17.5	8	-
2.19	22.5	17.5	93	79
2.19	45	17.5	88	79

Table 66. Synergistic Activity of In-Water Applications of Compound A Benzyl Ester, Cyhalofop-butyl, and Benfuresate Temary Herbicidal Compositions on Weed Control in a Rice 5 Cropping System.

Compound A Benzyl Ester	Cyhalofopbutyl	Benfuresate	Visual Weed Control (%) - 21 DAA
			ECHCG

115

gae/ha	gai/ha	gai/ha	Obs	Exp
4	0	0	25
8	0	0	45
16	0	0	99
0	45	0	30
0	0	150	0
4	45	150	95	48
8	45	150	95	62
16	45	150	100	99

Table 67. Synergistic Activity of In-Water Applications of Compound A Benzyl Ester, Cyhalofop-butyl, and Benzobicyclon Temary Herbicidal Compositions on Weed Control in a 5 Rice Cropping System.

Compound A Benzyl Ester	Cyhalofopbutyl	Benzobicyclon	Visual Weed Control (%) - 21 DAA
			ECHCG
gae/ha	gai/ha	gai/ha	Obs	Exp
4	0	0	25	-
0	45	0	30	-
0	0	100	20	-
4	45	100	100	58

Compound A Benzyl Ester	Cyhalofopbutyl	Benzobicyclon	Visual Weed Control (%) - 24 DAA
			ECHOR
gae/ha	gai/ha	gai/ha	Obs	Exp
4	0	0	0
8	0	0	0
16	0	0	10
0	90	0	25
0	0	25	10
0	0	50	10
4	90	25	35	33
8	90	25	40	33
16	90	25	100	39
4	90	50	20	33
8	90	50	100	33
16	90	50	85	39

Compound A Benzyl

Cyhalofopbutyl

Benzobicyclon

Visual Weed Control (%) - 24

116

Ester			DAA
			FIMMI
gae/ha	gai/ha	gai/ha	Obs	Exp
4	0	0	0
8	0	0	50
16	0	0	30
0	180	0	20
0	0	50	68
4	180	50	88	74
8	180	50	100	87
16	180	50	100	82

Table 68. Synergistic Activity of In-Water Applications of Compound A Benzyl Ester, Cyhalofop-butyl, and Pyraclonil Temary Herbicidal Compositions on Weed Control in a Rice Cropping System.

Compound A Benzyl Ester	Cyhalofopbutyl	Pyraclonil	Visual Weed Control (%) - 21 DAA
			ECHCG
gae/ha	gai/ha	gai/ha	Obs	Exp
4	0	0	25
8	0	0	45
16	0	0	99
0	45	0	30
0	0	22.5	30
4	45	22.5	100	63
8	45	22.5	100	73
16	45	22.5	100	100

Compound A Benzyl Ester	Cyhalofopbutyl	Pyraclonil	Visual Weed Control (%) - 21 DAA
			SCPMA
gae/ha	gai/ha	gai/ha	Obs	Exp
4	0	0	0
8	0	0	0
16	0	0	0
0	22.5	0	0
0	45	0	0
0	0	22.5	78
4	22.5	22.5	83	78
8	22.5	22.5	100	78

117

16	22.5	22.5	93	78
4	45	22.5	95	78
8	45	22.5	98	78
16	45	22.5	90	78

Table 69. Synergistic Activity of In-Water Applications of Compound A Benzyl Ester, Cyhalofop-butyl, and Mefenacet Temary Herbicidal Compositions on Weed Control in a Rice Cropping System.

Compound A Benzyl Ester	Cyhalofopbutyl	Mefenacet	Visual Weed Control (%) - 21 DAA
			CYPRO
gae/ha	gai/ha	gai/ha	Obs	Exp
4	0	0	3
8	0	0	33
0	90	0	0
0	180	0	0
0	0	75	0
0	0	150	0
4	90	75	15	3
8	90	75	55	33
4	90	150	75	3
8	90	150	50	33
4	180	75	68	3
8	180	75	60	33
4	180	150	35	3
8	180	150	63	33

Table 70. Synergistic Activity of In-Water Applications of Compound A Benzyl Ester, Cyhalofop-butyl, and Pretilachlor.

Compound A Benzyl Ester	Cyhalofopbutyl	Pretilachlor	Visual Weed Control (%) - 21 DAA
			CYPRO
gae/ha	gai/ha	gai/ha	Obs	Exp
4	0	0	3
8	0	0	33
0	180	0	0
0	0	25	0
0	0	50	0
4	180	25	30	3
8	180	25	100	33

118

4	180	50	35	3
8	180	50	55	33

Table 71. Synergistic Activity of In-Water Applications of Compound A Benzyl Ester, Metamifop, and Penoxsulam Temary Herbicidal Compositions on Weed Control in a Rice Cropping System.

Compound A Benzyl Ester	Penoxsulam	Metamifop	Visual Weed Control (%) - 24 DAA
			ECHOR
gae/ha	gai/ha	gai/ha	Obs	Exp
8	0	0	10
16	0	0	25
0	5	0	65
0	10	0	93
0	0	25	10
0	0	50	18
8	5	25	83	72
16	10	25	83	95
8	5	50	100	74
16	10	50	100	95

CYPRO	Cyperus rotundus L.	nutsedge, purple
ECHCG	Echinochloa crusgalli (L.) Beauv.	bamyardgrass
ECHOR	Echinochloa oryzoides (Ard.) Fritsch	watergrass, early
10 FIMMI	Fimbristylis miliacea (L.) Vahl	fringerush, globe
SCPJU	Schoenoplectus juncoides (Roxb.) Palla	bulrush, Japanese
SCPMA	Bolboschoenus maritimus (L.) Palla or
	Schoenoplectus maritimus (L.) Lye	clubrush, sea
gae/ha =	grams acid équivalent per hectare
15 gai/ha =	grams active ingrédient per hectare

Obs = observed value

Exp = expected value as calculated by Colby’s équation

DAA = days after application

Claims

1. A synergistic herbicidal composition comprising a herbicidally effective amount of (a) a or an agriculturally acceptable sait or ester thereof and (b) an ACCase inhibitor.

2. The composition of claim 1, wherein (a) is the compound of formula (I), a Cm alkyl ester of the compound of formula (I), or a benzyl ester of the compound of formula (I).

3. The composition of any of claims 1-2, wherein (b) is at least one compound, or an agriculturally acceptable sait, carboxylic acid, carboxylate sait, or ester thereof, selected from the group consisting of: clethodim, clodinafop-propargyl, cyhalofop-R-butyl, diclofop-methyl, fenoxaprop-P-ethyl, fluazifop-P-butyl, haloxyfop-R-methyl, metamifop, pinoxaden, profoxydim, quizalofop-P-ethyl, sethoxydim, and tralkoxydim.

4. The composition of any of claims 1-3, further comprising an agriculturally acceptable adjuvant or carrier.

5. The composition of any of claims 1 -4, further comprising a herbicide safener.

6. A method of controlling undesirable végétation which comprises contacting the végétation or the locus thereof with or applying to the soil or water to prevent the emergence or growth of végétation a herbicidally effective amount of (a) a compound of the formula (I)

nh₂ R zCl Τι ί ΌΗ il ΊΓ ⁿ 0 cr γ f H,C'° ®

or an agriculturally acceptable sait or ester thereof and (b) an ACCase inhibitor

7. The method of claim 6, wherein (a) is the compound of formula (I), a Cm alkyl ester of the compound of formula (I), or a benzyl ester of the compound of formula (I).

8. The method of any of claims 6-7, wherein (b) is at least one compound, or an agriculturally acceptable sait, carboxylic acid, carboxylate sait, or ester thereof, selected from the

120 group consisting of: clethodim, clodinafop-propargyl, cyhalofop-R-butyl, diclofop-methyl, fenoxaprop-P-ethyl, fluazifop-P-butyl, haloxyfop-R-methyl, metamifop, pinoxaden, profoxydim, quizalofop-P-ethyl, sethoxydim, and tralkoxydim.

9. The method of any of claims 6-8, wherein the undesirable végétation is controlled in direct-seeded, water-seeded and transplanted rice, cereals, wheat, barley, oats, rye, sorghum, com/maize, sugarcane, sunflower, oilseed râpe, canola, sugar beet, soybean, cotton, pineapple, pastures, grasslands, rangelands, fallowland, turf, tree and vine orchards, aquatics, industrial végétation management (IVM) or rights of way (ROW).

10. The method of any of claims 6-9, wherein the (a) and (b) are applied pre-emergently to the weed or the crop.

11. The method of any of claims 6-10, wherein the undesirable végétation is controlled in glyphosate-, 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitor-, glufosinate-, glutamine synthetase inhibitor-, dicamba-, phenoxy auxin-, pyridyloxy auxin-, synthetic auxin-, auxin transport inhibitor-, aryloxyphenoxypropionate-, cyclohexanedione-, phenylpyrazoline-, acetyl CoA carboxylase (ACCase) inhibitor-, imidazolinone-, sulfonylurea-, pyrimidinylthiobenzoate-, triazolopyrimidine-, sulfonylaminocarbonyltriazolinone-, acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors-, 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor-, phytoene desaturase inhibitor-, carotenoid biosynthesis inhibitor-, protoporphyrinogen oxidase (PPO) inhibitor-, cellulose biosynthesis inhibitor-, mitosis inhibitor-, microtubule inhibitor-, very long chain fatty acid inhibitor-, fatty acid and lipid biosynthesis inhibitor-, photosystem I inhibitor-, photosystem II inhibitor-, triazine-, or bromoxynil- tolérant crops.

12. The method of claim 11, wherein the tolérant crop possesses multiple or stacked traits conferring tolérance to multiple herbicides or multiple modes of action.

13. The method of any of claims 6-12, wherein the undesirable végétation comprises a herbicide résistant or tolérant weed.

14. The composition of any of claims 1-5, further comprising at least one compound selected from the group consisting of penoxsulam, bentazon-sodium, triclopyr, bispyribac-sodium, imazamox, benzobicyclon, quinclorac, glyphosate, glufosinate, benfuresate, fentrazamide, indanofan, ipfencarbazone, mefenacet, oxazichlomefone, pretilachlor, propyrisulfuron, pyraclonil, pyriftalid, and pyrimisulfan, or an âgriculturally acceptable sait, carboxylic acid, carboxylate sait, or ester thereof, in combination as a synergistic 3 way/temary mixture.