OA17277A - Herbicidal compositions comprising 4-amino3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3methoxyphenyl) pyridine-2-carboxylic acid. - Google Patents

Herbicidal compositions comprising 4-amino3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3methoxyphenyl) pyridine-2-carboxylic acid. Download PDF

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Publication number
OA17277A
OA17277A OA1201500026 OA17277A OA 17277 A OA17277 A OA 17277A OA 1201500026 OA1201500026 OA 1201500026 OA 17277 A OA17277 A OA 17277A
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OAPI
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compound
ester
formula
sait
inhibitor
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OA1201500026
Inventor
Carla N. YERKES
Richard K. Mann
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Dow Agrosciences Llc
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Abstract

Provided herein are synergistic herbicidal compositions containing (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 numbers 61/675,109 filed on July 24,2012 and 61/675,117 filed on July 24,2012, and United States utility patent application number 13/833,362 filed on March 15, 2013, each of these applications is incorporated herein by reference in its entirety.
Field
Provided herein are herbicidal compositions comprising (a) 4-amino-3-chloro-5-fluoro-6(4-chloro-2-fluoro-3-methoxyphenyl) pyridine-2-carboxylic acid or an agriculturally acceptable ester or sait thereof and (b) a dimethoxy-pyrimidine, such as a pyrimidinyloxybenzoic acid or a pyrimidinylthiobenzoic acid or agriculturally acceptable sait or esters thereof.
Provided herein are also methods of controlling undesirable végétation comprising applying (a) 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2carboxylic acid or an agriculturally acceptable ester or sait thereof and (b) a dimethoxypyrimidine, such as pyrimidinyloxybenzoic acids or pyrimidinylthiobenzoic acids or agriculturally acceptable salts or esters thereof.
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 of the invention provided herein includes herbicidal compositions comprising an herbicidally effective amount of (a) a compound of the formula (I)
or an agriculturally acceptable sait or ester thereof, and (b) at least one a dimethoxy-pyrimidine selected from the group consisting of: pyrimidinyloxybenzoic acids, pyrmidinylthiobenzoic acids, and agriculturally acceptable salts and esters thereof.
A second embodiment includes the mixture of the first embodiment in which formula (I) is présent in at least one of the following forms: a carboxylic acid, a carboxylate sait, an aralkyl, an alkyl ester, an unsubstituted benzyl, a substituted benzyl, a C1.C4 alkyl, and/or an n-butyl ester.
A third embodiment includes the mixture according to either the first or second embodiments wherein the (b) at least one dimethoxy-pyrimidine selected from the group consisting of: bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac-methyl or pyrimisulfan, or an agriculturally acceptable sait, carboxylic acid, carboxylate sait, or ester thereof of at least one of the aforementioned dimethoxy-pyrimidines.
A fourth embodiment includes the mixtures according to any of the first, second, or third embodiments in which the dimethoxy-pyrimidine in the mixture is bispyribac-sodium wherein the weight ratio of the compound of formula (I) to bispyribac-sodium given in units of gae/ha to gai/ha or gae/ha to gae/ha is selected from the group of ranges of ratios and ratios consisting of about: 1:75 to 43:1,1:0.8,1:0.4,1:1.6,1:1.4,1:0.6,1:0.3, 1:2.3,1:3,1:1.1,1:4.6,1.75:1, 2.5:1,
5:1, 1:70 to 40:1, 1:60 to 30:1,1:50 to 20:1,1:40 to 15:1,1:30 to 10:1,1:20 to 5:1,1:10 to 4:1, 1:5 to 1:1 and 10:1 to 1:9, or within any range defined between any pair of the foregoing values.
A fifth embodiment includes the mixtures according to any of the first, second, or third embodiments in which the dimethoxy-pyrimidine in the mixture is pyribenzoxim wherein the weight ratio of the compound of formula (I) to pyribenzoxim given in units of gae/ha to gai/ha or gae/ha to gae/ha is selected from the group of ranges of ratios and ratios consisting of about: 1:45 to 10:1, 1:8.8,1:4.4,1:2.2, 1:40 to 9:1,1:30 to 7:1,1:20 to 5:1,1:10 to 4:1 and 1:9, and 1:45, or within any range defined between any pair of the foregoing values.
A sixth embodiment includes the mixtures according to any of the first, second, or third embodiments in which the dimethoxy-pyrimidine in the mixture is pyriftalid wherein the weight ratio of the compound of formula (I) to pyriftalid given in units of gae/ha to gai/ha or gae/ha to gae/ha is selected from the group of ranges of ratios and ratios consisting of about: 1:150 to 3:1, 1:10, 1:21,1:2.6,1:5.2,1:2.5,1:10, 1:20,1:26, 1:10.3,1:6,1:100 to 2.5:1,1:75 to2:l, 1:50 to 1.5:1,1:30 to 1:1 and 1:21 to 0.75:1, or within any range defined between any pair ofthe foregoing values.
A seventh embodiment includes the mixtures according to any of the first, second, or third embodiments in which the dimethoxy-pyrimidine in the mixture is pyriminobac-methyl wherein the weight ratio of the compound of formula (I) to pyriminobac-methyl given in units of gae/ha to gai/ha or gae/ha to gae/ha is selected from the group of ranges of ratios and ratios consisting of about: 1:45 to 27:1, 1:9,1:4.4, 1:40 to 25:1,1:30 to 20:1,1:20 to 10:1,1:10 to 5:1 and 1:21 to 6:1 or within any range defined between any pair of the foregoing values.
An eighth embodiment includes the mixtures according to any of the first, second, or third embodiments in which the dimethoxy-pyrimidine in the mixture is pyrimisulfan wherein the weight ratio of the compound of formula (I) to pyrimisulfan given in units of gae/ha to gai/ha or gae/ha to gae/ha is selected from the group of ranges of ratios and ratios consisting of about:
1:100 to 30:1, 1:70 to 25:1,1:50 to 22:1,1:20 to 20:1,1:10 to 10:1,1:7 to 7;1 and 1:5 to 5:1, or within any range defined between any pair of the foregoing values.
A ninth embodiment includes any composition according to any of the first through the eighth embodiments wherein the mixture further comprises at least one an agriculturally acceptable agent seiected from the group consisting of an adjuvant, a carrier, or a safener.
A tenth embodiment includes methods of controliing undesirable végétation comprising the steps of applying or otherwise contacting végétation and/or soil, and/ or water with a herbicidally effective amount of at least one mixture according to any of the first through the ninth embodiments.
An eleventh embodiment includes methods according to the tenth embodiment wherein undesirable végétation is controlled by practicing at least one of the methods in at least one member of the group consisting of: in: direct-seeded, water-seeded, and/or 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), or rights-of-way (ROW).
A twelfth embodiment includes methods according to either of the tenth and eleventh embodiments wherein a herbicidally effective amount of the mixture is applied either pre- or post emergently to at least one of the following: a crop, a field, a ROW, or a rice paddy.
A thirteenth embodiment includes methods according to any of the tenth through the twelfth embodiments wherein the undesirable végétation may be controlled by practicing at least one of the methods on at least one plant that is résistant or tolérant to the members of the group consisting of: 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) 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-, protoporphyrinogen oxidase (PPO) inhibitor-, triazine-, and bromoxynil.
A fourteenth embodiment includes a at least one method according to any of the tenth through the thirteenth embodiments wherein a plant that is résistant or tolérant to at least one herbicide is treated, and where the résistant or tolérant crop possesses multiple or stacked traits conferring tolérance to multiple herbicides or inhibitors of multiple herbicide modes of action, in some embodiments the treated plant that expresses résistance to a herbicide is a itself undesirable végétation.
A fifteenth embodiment includes methods according to the fourteenth embodiment, wherein the résistant or tolérant weed is a biotype with résistance or tolérance to multiple herbicides, multiple chemical classes, inhibitors of multiple herbicide modes-of-action, or via multiple résistance mechanisms.
A sixteenth embodiment includes at least one of the methods according to either the fourteenth or fifteenth embodiments, wherein the résistant or tolérant undesirable plant is a biotype résistant or tolérant to at least one or more compounds that act according to at least one mode of action selected from the group consisting of: acetolactate synthase (ALS) inhibitors or acetohydroxy acid synthase (AHAS), photosystem II inhibitors, acetyl CoA carboxylase (ACCase) inhibitors, synthetic auxins, auxin transport inhibitors, photosystem I inhibitors, 5enolpyruvylshikimate-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-hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitors, mitosis inhibitors, cellulose biosynthesis inhibitors, herbicides with multiple modes-of-action, quinclorac, arylaminopropionic acids, difenzoquat, endothall, or organoarsenicals.
A seventeenth embodiment includes methods of controlling undesirable végétation comprising the step of applying a herbicidally effective amount of at least one mixture according to the fourth embodiment wherein the amount of the mixture is applied at a rate, expressed in gai/ha or gae/ha of bispyribac-sodium selected from the group of rates and ranges of rates consisting of, about: 1, 5, 7,10,14,20,40,70, 80, and 100, or within any range defined between any pair of the foregoing values.
A eighteenth embodiment includes methods according to either of the fourth and sixteenth embodiments wherein the controlled plant is at least one plant selected from the group consisting of: LEFCH, ECHCG, ECHOR, SCPMA, and CYPRO, still other embodiments include controlling plants from the généra consisting of: Leptochloa, Echinochloa, Bolboschoenus, and Cyperus.
An nineteenth embodiment includes methods of controlling undesirable végétation comprising the step of applying a herbicidally effective amount of at least one a mixture according to the fifth embodiment wherein the amount of the mixture is applied at a rate, expressed in gai/ha or gae/ha of pyribenzoxim selected from the group of rates and ranges of rates consisting of, about: 70,15 to 60, and 2 to 300, or within any range defined between any pair of the foregoing values.
A twentieth embodiment includes methods according to either of the fifth and nineteenth embodiments wherein the controlled plant is at least one plant selected from the group consisting of: ECHCG, still other embodiments include controlling plants from the généra consisting of: Echinochloa.
A twenty-first embodiment inciudes methods of controlling undesirable végétation comprising the step of applying a herbicidally effective amount of at least one a mixture according to the sixth embodiment wherein the amount of the mixture is applied at a rate, expressed in gai/ha or gae/ha of pyriftalid selected from the group of rates and ranges of rates consisting of, about: 1:150 to 3:1,1:10.3,1:21,1:2.6,1:5.2,1:2.5 and 1:21 to 0.75:1 or within any range defined between any pair of the foregoing values.
A twenty-second embodiment inciudes methods according to either of the sixth and twenty-second embodiments wherein the controlled plant is at least one plant selected from the group consisting of: BRAPP, LEFCH, CYPRO and FIMMI, still other embodiments include controlling plants from the généra consisting of: Leptochloa, Cypenis, Fimbristylis and Brachiaria.
A twenty-third embodiment inciudes methods of controlling undesirable végétation comprising the step of applying a herbicidally effective amount of at least one a mixture according to the seventh embodiment wherein the amount of the mixture is applied at a rate, expressed in gai/ha or gae/ha of pyriminobac-methyl selected from the group of rates and ranges of rates consisting of, about: 1:45 to 27:1, 5.5,11.25,22.5,45,90,180 and 1:21 to 6:1 or within any range defined between any pair of the foregoing values.
A twenty-fourth embodiment inciudes methods according to either of the seventh and twenty-third embodiments wherein the controlled plant is at least one plant selected from the group consisting of: DIGSA, IPOHE, LEFCH, ECHCO, FIMMI, SCPMA and CYPRO, still other embodiments include controlling plants from the généra consisting of: Digitaria, Ipomoea, Leptochloa, Echinochloa, Fimbristylis, Bolboschoenus and Cyperus.
A twenty-fifth embodiment inciudes methods of controlling undesirable végétation comprising the step of applying a herbicidally effective amount of at least one a mixture according to the seventh embodiment wherein the amount of the mixture is applied at a rate, expressed in gai/ha or gae/ha of pyrimisulfan selected from the group of rates and ranges of rates consisting of, about: 5,20, 50,100,150,200, and 300, or within any range defined between any pair of the foregoing values.
A twenty-sixth embodiment includes methods according to either of the seventh and twenty-fifth embodiments wherein the controlled plant is at least one plant selected from the group consisting of: CYPRO, ECHCG, ECHCO, LEFCH, SCPMA, DIGSA, IPOHE, and FIMMI, still other embodiments include controlling plants from the généra consisting of: Cyperus, Digitaria, Echinochloa, Fimbristylis, Ipomoea, Leptochloa, Schoenoplectus, and Bolboschoenus.
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) a dimethoxy-pyrimidine. The compositions may also include an agriculturally acceptable adjuvant or carrier.
Provided herein are also methods of controlling undesirable végétation comprising applying (a) a compound of formula (I) or an agriculturally acceptable ester or sait thereof and (b) a dimethoxy-pyrimidine herbicide or an agriculturally acceptable sait or ester thereof. Detailed Description
DEFINITIONS
As used herein, the compound of formula (I) has the following structure:
NH2
Cl
OH
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.
Pyrimidineoxycarboxylic acids contain in certain embodiments the following core structure:
which can be substituted with one or more substituents, and salts and esters thereof. The phenyl and pyrimidine may independently be part of a multicyclic ring system. The oxygen connected to both the pyrimidine and phenyl may be replaced with another heteroatom, e.g., S. Without being limited to any theory, the compounds inhibit acetolactate synthase (ALS) or (AHAS) acetohydroxyacid synthase (AHAS), the first common enzyme in the biosynthesis of the branched chain amino acids.
Exemplary pyrimidinylthiobenzoate acids or salts or esters thereof include, but are not limited to bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac-methyl and pyrimisulfan, agriculturally acceptable dérivatives, e.g., carboxylic acid, carboxylate sait, or ester thereof.
As used herein, bispyribac-sodium is sodium 2,6-bis[(4,6-dimethoxy-2pyrimidinyl)oxy]benzoate and possesses the following structure:
The compound has been described in Tomlin, C., ed. A World Compendium The Pesticide Manual. 15th ed. Alton: BCPC Publications, 2009 (hereafter “The Pesticide Manual, Fifteenth Edition, 2009.”). Exemplary uses ofbispyribac-sodium include its use to control grasses, sedges and broadleaf weeds, e.g., in direct-seeded and water-seeded rice and in turf.
As used herein, pyribenzoxim is diphenylmethanone 0-[2,6-bis[(4,6-dimethoxy-2pyrimidinyl)oxy]benzoyl]oxime and possesses the following structure:
The compound is described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of pyribenzoxim include its use for post-emergence control of bamyard grass, blackgrass and polygonums, e.g., in rice, wheat and zoysiagrass.
As used herein, pyriftalid is 7-[(4,6-dimethoxy-2-pyrimidinyl)thio]-3-methyl-l(3/7)isobenzofuranone and possesses the following structure:
in the compound is described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of pyriftalid include its use for post-emergence, broad-spectrum control of weed, e.g., in rice.
As used herein, pyriminobac-methyl is methyl 2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]-6[l-(methoxyimino)ethyl]benzoate and possesses the following structure:
The compound is described in The Pesticide Manual, Fifteenth Edition, 2009.
Exemplary uses of pyriminobac-methyl include its use for early post-emergence control of bamyard grass, e.g., in paddy rice.
As used herein, pyrimisulfan is 7V-[2-[(4,6-dimethoxy-2-pyrimidinyl)hydroxymethyl]-6(methoxymethyl)phenyl]-l,l-difluoromethanesulfonamide and possesses the following structure:
CF2H
Its herbicidal activity is exemplified in the Journal of Pesticide Science (Tokyo, Japan) (2012), 37(1), 62-68. Pyrimisulfan can be used, e.g., as a herbicide for the control of rice weeds in rice fields. 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 ofplants 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 limited to applications to the végétation or locus thereof, e.g., application to the area adjacent to the végétation, as well as pre-emergence, post-emergence, 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 corresponding carboxylic acid which, depending on the pH, may be in the dissociated or undissociated form.
Exemplary salts inciude those derived from alkali or alkaline earth metals and those derived from ammonia and amines. Exemplary cations inciude sodium, potassium, magnésium, and aminium cations of the formula:
r'r2r3r4n+ 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 substîtuted by one or more hydroxy, C1-C4 alkoxy, C1-C4 alkylthio orphenyl 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, orbenzylamine or with a tetraalkylammonium hydroxide, such as tétraméthylammonium hydroxide or choline hydroxide.
Exemplary esters inciude 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 substîtuted benzyl alcohols. Benzyl alcohols may be substîtuted with from 1 -3 substituents independently selected from halogen, C1-C4 alkyl or Ct-C4 alkoxy. Esters can be prepared by coupling of the acids with the alcohol using any number of suitable 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) nh2
Cl
OH or an agriculturally acceptable sait or ester of thereof, and (b) a dimethoxy-pyrmidine or agriculturally acceptable sait or ester thereof.
Provided herein are also methods of controlling undesirable végétation comprising contacting the végétation or the locus thereof, i.e., the area 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) or agriculturally acceptable sait or ester thereof and (b) a dimethoxy-pyrimidine. 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 dimethoxy-pyrimidine, 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. 9th ed. 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 antagoniste 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 certain embodiments, the dimethoxy-pyrimidine is bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac-methyl or pyrimisulfan or an agriculturally acceptable dérivative thereof.
In some embodiments, the compound of formula (I) or sait or ester thereof and bispyribac sodium, pyribenzoxim, pyriftalid, pyriminobac-methyl and pyrimisulfan or an agriculturally acceptable sait or ester thereof, are formulated in one composition, tank mixed, applied simultaneously, or applied sequentially.
Herbicidal activity is exhibited by the compounds when they are applied dîrectly 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 can 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-, 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 inhibitor14 tolérant-, 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, triazolopyrimidines, 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, 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 empioyed. In some embodiments, the compositions described herein and other complementary herbicides are applied at the same time, either as a combination formulation, as a 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, range and pasture, fallowland, row crops (e.g., com/maize, sugarcane, sunflower, oilseed râpe, canola, sugar beet, soybean, cotton), turf, tree and vine orchards, plantation crops, vegetables,and omamental species, aquatic or non-crop settings, (e.g., rights-of-way, industrial végétation management).
In some embodiments, the methods provided herein are utilized to control undesirable végétation in rice. In certain embodiments, the undesirable végétation is Brachiariaplatyphylla
Y (Groseb.) Nash or Urochloa platyphylla (Nash) R.D. Webster (broadleaf signalgrass, BRAPP), Digitaria sanguinalis (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), Echinochloa polystachya (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.Clarke (tidalmarsh flatsedge, 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), Alternantheraphiloxeroides (Mart.) Griseb. (alligatorweed, ALRPH), Alisma plantago-aquatica L. (common waterplantain, ALSPA), Amaranthus species, (pigweeds and amaranths, AMASS), Ammannia coccinea Rottb. (redstem, AMMCO), Commelina benghalensis 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), Lindernia 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
L· (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 midtiflorum 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), Lamiumpurpureum 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 carrot, 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. Ri ch.) Stapf. or Urochloa brizantha (Hochst. ex A. Rich.) R.D. (beard grass, BRABR), Brachiaria platyphylla (Groseb.) Nash or Urochloaplatyphylla (Nash) R.D. Webster (broadleaf signalgrass, BRAPP), Brachiariaplantaginea (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 midtiflorum Lam. (Italian ryegrass, 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, AMASS), 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. (hairy 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 canot, 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. (Canadian 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), Solarium ptychanthum Dunal (eastem black nightshade, SOLPT), Tridaxprocumbens L. (coat buttons, TRQPR), orXanthium 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 Bellisperennis 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 inciuding Cyperus, Digitaria, Echinochloa, Fimbristylis, Ipomoea, Leptochloa, and Schoenoplectus.
In some embodiments, the combination of compound (I) or agriculturally acceptable ester or sait thereof and bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac-methyl and pyrimisulfan or agriculturally acceptable sait or ester thereof are used to control Cyperus rotundus, Digitaria sanguinalis, Echinochloa crus-galli, Echinochloa colona, Fimbristylis miliacea, Ipomoea hederacea, Leptochloa chinensis, and Schoenoplectus maritimus or Bolboschoenus maritimus.
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, dimethoxy-pyrimidines, triazolopyrimidines, and 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 (e.g., clomazone, amitrole, aclonifen), phytoene desaturase (PDS) inhibitors (e.g., amides, anilidex, furanones, phenoxybutan-amides, pyridiazinones, pyridines), 4-hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitors (e.g., callistemones, isoxazoles, pyrazoles, triketones), cellulose biosynthesis inhibitors (e.g., nitriles, benzamides, quinclorac, triazolocarboxamides), 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 modes-ofaction, 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 a 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 some embodiments, an agriculturally acceptable ester or sait of bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac-methyl and pyrimisulfàn is employed in the methods or compositions described herein. In certain embodiments, the sodium sait of bispyribac 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 bispyribac-sodium or carboxylic acid or ester thereof or other bispyribac sait. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to bispyribac-sodium or carboxylic acid or ester thereof or other bispyribac sait is within the range of from about 1:75 to about 43:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to bispyribac-sodium or sait or ester thereof is within the range of from about 1:9 to about 10:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to bispyribac-sodium or carboxylic acid or ester thereof or other bispyribac sait is within the range of from about 1:10 to about 7:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to bispyribac-sodium or carboxylic acid or ester thereof or other bispyribac sait is within the range of from about 1:5 to about 3.5:1. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl or n-butyl ester and bispyribac-sodium. In one embodiment, the composition comprises the compound of formula (I) and bispyribacsodium, wherein the weight ratio of the compound of formula (I) to the bispyribac-sodium is about 1:3 to about 3.5:1. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and bispyribac-sodium, wherein the weight ratio of the benzyl ester of the compound of formula (I) to bispyribac-sodium is about 1:5 to about 2.5:1. In one embodiment, the composition comprises the n-butyl ester of the compound of formula (I) and bispyribac-sodium, wherein the weight ratio of the n-butyl ester of the compound of formula (I) to bispyribac-sodium is about 1:1.1 to about 1.75:1. 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 9 grams active ingrédient per hectare (gai/ha) to about 450 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 12 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 bispyribac-sodium or carboxylic acid or ester thereof or other bispyribac sait, e.g., sequentialiy or simultaneously. In some embodiments, the bispyribacsodium or carboxylic acid or ester thereof or other bispyribac sait is applied at a rate from about 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 2 g acid équivalent (ae)/ha to about 300 gae/ha. In some embodiments, the bispyribac-sodium or carboxylic acid or ester thereof or other bispyribac sait is applied at a rate from about 3 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 4 g acid équivalent per hectare (gae/ha) to about 150 gae/ha. In some embodiments, the bispyribac-sodium or carboxylic acid or ester thereof or other bispyribac sait is applied at a rate from about 7 gai/ha to about 40 gai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 8.75 g acid équivalent per hectare (gae/ha) to about 70 gae/ha. In certain embodiments, the methods utilize the compound of formula (I), or its benzyl or n-butyl ester and bispyribac-sodium. In one embodiment, the methods utilize the compound of formula (I) and bispyribac-sodium, 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 bispyribac-sodium is applied at a rate of about 10 gai/ha to about 40 gai/ha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and bispyribac-sodium, 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 70 gae/ha, and bispyribac-sodium is applied at a rate of about 7 gai/ha to about 40 gai/ha. In one embodiment, the methods utilize the n-butyl ester of the compound of formula (I) and bispyribac-sodium, wherein the n-butyl ester of the compound of formula (I) is applied at a rate of about 35 g acid équivalent per hectare (gae/ha) to about 70 gae/ha, and bispyribac-sodium is applied at a rate of about 40 gai/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or sait or ester thereof in combination with bispyribac-sodium or carboxylic acid or ester thereof or other bispyribac sait are used to control LEFCH, ECHCG, ECHOR, CYPRO, or SCPMA.
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 pyribenzoxim 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 pyribenzoxim or sait or ester thereof 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 pyribenzoxim 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 pyribenzoxim. 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 17 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 20 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 pyribenzoxim, e.g., sequentially or simultaneously. In some embodiments, the pyribenzoxim 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 2 g acid équivalent (ae)/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 pyribenzoxim.
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 pyribenzoxim 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 pyribenzoxim or sait or ester thereof 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 pyribenzoxim or sait or ester thereof is within the range of from 1:9 to about 1:4. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and pyribenzoxim. 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 17 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 20 grams active ingrédient per hectare (gai/ha) to about 200 gai/ha based on the total amount of active ingrédients in the composition. In further spécial embodiments, the composition is applied at an application rate of from about 78 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 pyribenzoxim, e.g., sequentially or simultaneously. In some embodiments, the pyribenzoxim 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 2 g acid équivalent (ae)/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 pyribenzoxim and are used to control 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 pyriftalid 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 pyriftalid or carboxylic acid or carboxylate sait thereof or other ester is within the range of from about 1:150 to about 3:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to pyriftalid or carboxylic acid or carboxylate sait thereof or other ester is within the range of from about 1:20 to about 1:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to pyriftalid or carboxylic acid or carboxylate sait thereof or other ester is within the range of from about 1:36 to about 2:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to pyriftalid or carboxylic acid or carboxylate sait thereof or other ester is within the range of from about 1:18 to about 1:1.4. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl or n-butyl ester and pyriftalid. In one embodiment, the composition comprises the compound of formula (I) and pyriftalid, wherein the weight ratio of the compound of formula (I) to pyriftalid is about 1:18 to about 1:1.4. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and pyriftalid, wherein the weight ratio of the benzyl ester of the compound of formula (I) to pyriftalid is about 1:18 to about 1:2.6. 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 102 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 49 grams active ingrédient per hectare (gai/ha) to about 125 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 pyriftalid or carboxylic acid or carboxylate sait thereof or other ester, e.g., sequentially or simultaneously. In some embodiments, the pyriftalid or carboxylic acid or carboxylate sait thereof or other ester is applied at a rate from about 45 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 (ae)/ha to about 300 gae/ha. In some embodiments, the pyriftalid or carboxylic acid or carboxylate sait thereof or other ester is applied at a rate from about 20 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 2 g acid équivalent per hectare (gae/ha) to about 70 gae/ha. In some embodiments, the pyriftalid or carboxylic acid or carboxylate sait thereof or other ester is applied at a rate from about 45 gai/ha to about 90 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 or n-butyl ester and pyriftalid. In one embodiment, the methods utilize the compound of formula (I) and pyriftalid, 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 pyriftalid is applied at a rate of about 45 gai/ha to about 90 gai/ha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and pyriftalid, 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 pyriftalid is applied at a rate of about 45 gai/ha to about 90 gai/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or sait or ester thereof in combination with pyriftalid or carboxylic acid or carboxylate sait thereof or other ester are used to control BRAPP, LEFCH, CYPRO, or FIMMI.
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 pyriminobac-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 pyriminobac-methyl or carboxylic acid or carboxylate sait thereof or other ester is within the range of from about 1:45 to about 27:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to pyriminobac-methyl or carboxylic acid or carboxylate sait thereof or other ester is within the range of from about 1:20 to about 3:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to pyriminobac-methyl or carboxylic acid or carboxylate sait thereof or other ester is within the range of from about 1:20 to about 4:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to pyriminobac-methyl or carboxylic acid or carboxylate sait thereof or other ester is within the range of from about 1:9 to about 1.6:1. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl or n-butyl ester and pyriminobac-methyl. In one embodiment, the composition comprises the compound of formula (I) and pyriminobac-methyl, wherein the weight ratio of the compound of formula (I) to pyriminobac-methyl is about 1:5 to about 1.6:1. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and pyriminobacmethyl, wherein the weight ratio of the benzyl ester of the compound of formula (I) to pyriminobac-methyl is about 1:9 to about 1.6:1. 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 390 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 125 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 pyriminobac-methyl or carboxylic acid or carboxylate sait thereof or other ester, e.g., sequentially or simultaneously. In some embodiments, the pyriminobac-methyl or carboxylic acid or carboxylate sait thereof or other ester is applied at a rate from about 11 gr ai/ha to about 90 gai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 gai/ha to about 300 g acid équivalent (ae)/ha. In some embodiments, the pyriminobac-methyl or carboxylic acid or carboxylate sait thereof or other ester is applied at a rate from about 5 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 2 g acid équivalent per hectare (gae/ha) to about 140 gae/ha. In some embodiments, the pyriminobac-methyl or carboxylic acid or carboxylate sait thereof or other ester is applied at a rate from about 11.25 gai/ha to about 90 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 70 gae/ha. In certain embodiments, the methods utilize the compound of formula (I), or its benzyl or n-butyl ester and pyriminobacmethyl. In one embodiment, the methods utilize the compound of formula (I) and pyriminobacmethyl, 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 70 gae/ha, and pyriminobac-methyl is applied at a rate of about 11.25 gai/ha to about 90 gai/ha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and pyriminobac-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 35 gae/ha, and pyriminobac-methyl is applied at a rate of about 11.25 gai/ha to about 90 gai/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or sait or ester thereof in combination with pyriminobac-methyl or carboxylic acid or carboxyiate sait thereof or other ester are used to control DIGSA, IPOHE, LEFCH, ECHCO, FIMMI, SCPMA, 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 pyrimisulfan or 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 pyrimisulfan or sait or ester thereof is within the range of from about 1:100 to about 30:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to pyrimisulfan or sait or ester thereof is within the range of from 1:45 to about 10:1. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl or n-butyl ester and pyrimisulfan. 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 12 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 15 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 pyrimisulfan or sait or ester thereof, e.g., sequentially or simultaneously. In some embodiments, the pyrimisulfan or sait or ester thereof is applied at a rate from about 10 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 certain embodiments, the methods utilize compound of formula (I) or its benzyl or n-butyl ester and pyrimisulfan.
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 inciude, 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, 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, clethodim, cliodinate, clodinafop-propargyl, clofop, clomazone, clomeprop, cloprop, cloproxydim, clopyralid, cloransulam-methyl, CMA, copper sulfate, CPMF, CPPC, credazine, cresol, cumyluron, cyanatryn, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cycluron, cyhalofop-butyl, cyperquat, cyprazine, cyprazole, cypromid, daimuron, dalapon, dazomet, delachlor, desmedipham, desmetryn, di-allate, dicamba, dichlobenil, dichloralurea, dichlormate, dichlorprop, dichlorprop-P, diclofop-methyl, 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, DMPA, 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, fenoxaprop, fenoxaprop-P-ethyl, fenoxaprop-P-ethyl + isoxadifen-ethyl, fenoxasulfone, fenteracol, fenthiaprop, fentrazamide, fenuron, ferrous sulfate, flamprop, flamprop-M, flazasulfuron, florasulam, fluazifop, fluazifop-P-butyl, 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, halosafen, halauxifen, halauxifen-methyl, halosulfuron-methyl, haloxydine, haloxyfop-methyl, haloxyfop-P-methyl, 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, metamifop, metamitron, metazachlor, metazosulfuron, metflurazon, methabenzthiazuron, methalpropalin, methazole, methiobencarb, methiozolin, methiuron, methometon, methoprotryne, methyl bromide, methyl isothiocyanate, methyldymron, metobenzuron, metobromuron, metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monalide, monisouron, monochloroacetic acid, monolinuron, monuron, morfamquat, MSMA, naproanilide, napropamide, naptalam, neburon, nicosulfuron, nipyraclofen, nitralin, nitrofen, nitrofluorfen, norflurazon, noruron, OCH, orbencarb, or/Ao-dichlorobenzene, 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, pinoxaden, piperophos, potassium arsenite, potassium azide, potassium cyanate, pretilachlor, primisulfuron-methyl, procyazine, prodiamine, profluazol, profluralin, profoxydim, 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, pyributicarb, pyriclor, pyridafol, pyridate, pyrimisulfan, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quinonamid, quizalofop, quizalofop-P-ethyl, rhodethanil, rimsulfuron, saflufenacil, Smetolachlor, sebuthylazine, secbumeton, sethoxydim, 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, tralkoxydim, 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, optically 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, triazolopyrimidines, sulfonylaminocarbonyltriazolinones, acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors, 4-hydroxyphenyl-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 auxin-tolerant, pyridyloxy auxin-tolerant, auxin-tolerant, auxin transport inhibitor-tolerant, aryloxyphenoxypropionatetolerant, cyclohexanedione-tolerant, phenylpyrazoline-tolerant, ACCase-tolérant, imidazolinonetolerant, sulfonylurea-tolerant, pyrimidinylthiobenzoate-tolerant, 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 inhibitor-tolerant, 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, bromoxyniltolerant, 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, as a tank mix or as a sequential application.
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 JV-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, a-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, ethyl ene, 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 a dimethoxy-pyrimidine to cause a preferentially advantageous effect on plants.
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 directiy 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; natural 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, π-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, JV-methyl-2pyrrolidinone, A/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 empioyed 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 alcoholCj6 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 trimethyl ammonium 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, safflower 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 empioyed 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 3.0 weight percent active ingrédient and in certain embodiments contain about 0.01 to 1.0 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 and II 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 fungicide 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 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
OH
Compound A Acid nh2
Compound A Benzyl Ester
Other herbicidal components were applied on an active ingrédient basis and included the dimethoxy-pyrimidine acid acetolactate synthase (ALS)-inhibiting herbicides bispyribac-sodium formulated as Régiment® 80WP, pyribenzoxim (technical grade material), pyriminobac-methyl formulated as Hie-Clean® 1.2% GR dissolved in water, and pyriftalid (technical grade material).
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+/-0.005% (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 were 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 of the formulated compounds were 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 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 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 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 ofthe synergistic and antagonistic response ofherbicide 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 1-6.
Table 1. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and BispyribacSodium Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound A Benzyl Ester BispyribacSodium Visual Weed Control (%) - 20 DAA
LEFCH
gae/ha gai/ha Obs Exp
8.75 0 10 -
17.5 0 20 -
0 7 0 -
0 14 0 -
8.75 7 25 10
17.5 7 40 20
8.75 14 25 10
17.5 14 60 20
Table 2. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Pyribenzoxim Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound A Benzyl Ester Pyribenzoxim Visual Weed Control (%) - 20 DAA
ECHCG
gae/ha gai/ha Obs Exp
8 0 75 -
16 0 85 -
0 70 85 -
8 70 99 96
16 70 99 98
Table 3. Synergistic Activity of Foliar-Applied Compound A Acid and Pyriminobac-methyl
Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound A Acid Pyriminobacmethyl Visual Weed Control (%) - 24 DAA
DIGSA IPOHE
gae/ha gai/ha Obs Exp Obs Exp
4.38 0 20 10
8.75 0 25 10
17.5 0 25 30
0 11.25 0 10
0 22.5 0 10
4.38 11.25 30 20 15 19
8.75 11.25 45 25 30 19
17.5 11.25 60 25 60 37
4.38 22.5 15 20 20 19
8.75 22.5 40 25 20 19
17.5 22.5 40 25 45 37
Compound A Acid Pyriminobacmethyl Visual Weed Control (%) - 24 DAA
IPOHE
gae/ha gai/ha Obs Exp
17.5 0 25 -
35 0 48 -
0 90 20 -
17.5 90 43 40
35 90 70 58
Table 4. Synergistic Activity ofFoliar-Applied Compound A Benzyl Ester and Pyriminobacmethyl Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound A Benzyl Ester Pyriminobacmethyl Visual Weed Control (%) - 24 DAA
LEFCH IPOHE
gae/ha gai/ha Obs Exp Obs Exp
4.38 0 0 10 -
8.75 0 0 15 -
17.5 0 10 30 -
0 11.25 0 10 -
0 22.5 0 10 -
4.38 11.25 20 0 25 19
8.75 11.25 15 0 40 24
17.5 11.25 40 10 30 37
4.38 22.5 15 0 40 19
8.75 22.5 15 0 20 24
17.5 22.5 40 10 40 37
Compound A Benzyl Ester Pyriminobacmethyl Visual Weed Control (%) - 21 DAA
IPOHE
gae/ha gai/ha Obs Exp
17.5 0 43 -
0 90 20 -
17.5 90 65 54
Table 5. Synergistic Activity of Foliar-Applied Compound A Acid and Pyriftalid Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound A Acid Pyriftalid Visual Weed Control (%) - 22 DAA
BRAPP
gae/ha gai/ha Obs Exp
4.38 0 45 -
0 45 0 -
0 90 0 -
4.38 45 65 45
4.38 90 65 45
Table 6. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Pyriftalid Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound A Benzyl Ester Pyriftalid Visual Weed Control (%) - 22 DAA
LEFCH
gae/ha gai/ha Obs Exp
17.5 0 25 -
0 45 0 -
0 90 0 -
17.5 45 40 25
17.5 90 35 25
BRAPP
DIGSA
ECHCG
IPOHE
Brachiaria platyphylla (Griseb.) Nash Digitaria sanguinalis (L.) Scop. Echinochloa crusgalli (L.) Beauv. Ipomoea hederacea Jacq. Leptochloa chinensis (L.) Nees
LEFCH 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 signalgrass, broadleaf crabgrass, large Bamyardgrass momingglory, ivyleaf sprangletop, Chinese
Example II. Evaluation of In-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 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 cm 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 1 ighting 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 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 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:
<3 h3ct
Compound A Acid
Compound A η-Butyl Ester
Compound A Benzyl Ester
Other herbicidal components were applied on an active ingrédient basis and included the dimethoxy-pyrimidine acid acetolactate synthase (ALS)-inhibiting herbicides bispyribac-sodium formulated as Régiment® 80 WP,, pyriminobac-methyl formulated as Hie-Clean®, and pyriftalid (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 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 was placed in an individual 100 to 200 mL glass vial and was dissolved in a volume of acetone to obtain concentrated stock solutions. Ifthe 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) crop 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, individually and sequentially, into the aqueous layer of the paddy. Controi 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 controi 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.
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. .
Some of the compounds tested, application rates employed, plant species tested, and results are given in Tables 7-13.
Table 7. Synergistic Activity of In-Water Applications of Compound A Acid and BispyribacSodium Herbicidal Compositions on Weed Controi in a Rice Cropping System.
Compound A Acid Bispyribac sodium Visual Weed Controi (%) - 20 DAA
ECHCG
gae/ha gai/ha Obs Exp
8.75 0 0 -
17.5 0 35 -
35 0 55 -
0 10 20 -
0 20 35 -
8.75 10 45 20
17.5 10 30 48
35 10 80 64
8.75 20 60 35
17.5 20 100 58
35 20 99 71
Compound A Acid Bispyribac sodium Visual Weed Control (%) - 20 DAA
ECHOR LEFCH SCPMA
gae/ha gai/ha Obs Exp Obs Exp Obs Exp
42.4 0 18 - 15 - 0 -
0 40 30 - 28 - 38 -
42.4 40 62 42 58 38 90 38
Table 8. Synergistic Activity of In-Water Applications of Compound A Benzyl Ester and
Bispyribac-Sodium Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound A Benzyl Ester Bispyribac sodium Visual Weed Control (%) - 20 DAA
CYPRO
gae/ha gai/ha Obs Exp
4.38 0 50 -
0 10 0 -
0 20 0 -
4.38 10 70 50
4.38 20 95 50
Compound A Benzyl Ester Bispyribac sodium Visual Weed Control (%) - 20 DAA
SCPMA
gae/ha gai/ha Obs Exp
35 0 0 -
70 0 0 -
0 40 38 -
35 40 100 38
70 40 95 38
Table 9. Synergistic Activity of In-Water Applications of Compound A n-Butyl Ester and Bispyribac-Sodium Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound A n-Butyl Ester Bispyribac sodium Visual Weed Control (%) - 20 DAA
ECHOR
gae/ha gai/ha Obs Exp
35 0 35 -
70 0 40 -
0 40 30 -
35 40 68 55
70 40 100 58
Compound A n-Butyl Ester Bispyribac sodium Visual Weed Control (%) - 20 DAA
SCPMA
gae/ha gai/ha Obs Exp
70 0 0 -
0 40 38 -
70 40 75 38
Table 10. Synergistic Activity of In-Water Applications of Compound A Acid and Pyriminobacmethyl Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound A Acid Pyriminobacmethyl Visual Weed Control (%) - 21 DAA
ECHCO
gae/ha gai/ha Obs Exp
8.75 0 0 -
17.5 0 20 -
0 22.5 40 -
8.75 22.5 100 40
17.5 22.5 95 52
Compound A Acid Pyriminobacmethyl Visual Weed Control (%) - 21 DAA
LEFCH
gae/ha gai/ha Obs Exp
8.75 0 0 -
17.5 0 0 -
0 45 80 -
8.75 45 100 80
17.5 45 100 80
Compound A Acid Pyriminobacmethyl Visual Weed Control (%) - 21 DAA
FIMMI SCPMA
gae/ha gai/ha Obs Exp Obs Exp
8.75 0 50 0 -
17.5 0 85 0 -
35 0 85 0 -
0 22.5 0 0 -
0 45 0 0 -
8.75 22.5 80 50 0 0
17.5 22.5 100 85 30 0
35 22.5 100 85 100 0
8.75 45 85 50 95 0
17.5 45 100 85 30 0
35 45 100 85 95 0
Compound A Acid Pyriminobacmethyl Visual Weed Control (%) - 20 DAA
SCPMA
gae/ha gai/ha Obs Exp
35 0 0 -
70 0 0 -
0 90 43 -
35 90 53 43
70 90 85 43
Table 11. Synergistic Activity of In-Water Applications of Compound A Benzyl Ester and
Pyriminobac-methyl Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound A Benzyl Ester Pyriminobacmethyl Visual Weed Control (%) - 21 DAA
CYPRO
gae/ha gai/ha Obs Exp
4.38 0 0 -
8.75 0 20 -
17.5 0 10 -
0 22.5 0 -
4.38 22.5 30 0
8.75 22.5 40 20
17.5 I 22.5 I 90 I 10 I
Compound A Benzyl Ester Pyriminobacmethyl Visual Weed Control (%) - 21 DAA
SCPMA
gae/ha gai/ha Obs Exp
4.38 0 0 -
8.75 0 0 -
0 22.5 0 -
0 45 0 -
4.38 22.5 60 0
8.75 22.5 20 0
4.38 45 20 0
8.75 45 20 0
Compound A Benzyl Ester Pyriminobacmethyl Visual Weed Control (%) - 20 DAA
SCPMA
gae/ha gai/ha Obs Exp
35 0 0 -
0 90 43 -
35 90 65 43
Table 12. Synergistic Activity of In-Water Applications of Compound A Acid and Pyriftalid Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound A Acid Pyriftalid Visual Weed Control (%) - 21 DAA
CYPRO
gae/ha gai/ha Obs Exp
8.75 0 30
17.5 0 40
35 0 70
0 45 0
0 90 0
8.75 45 85 30
17.5 45 20 40
35 45 80 70
8.75 90 50 30
17.5 90 50 40
35 90 85 70
Table 13. Synergistic Activity of In-Water Applications of Compound A Benzyl Ester and Pyriftalid Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound A Benzyl Ester Pyriftalid Visual Weed Control (%) - 21 DAA
CYPRO
gae/ha gai/ha Obs Exp
4.38 0 30 -
8.75 0 60 -
0 45 0 -
0 90 0 -
4.38 45 40 30
8.75 45 85 60
4.38 90 50 30
8.75 90 100 60
Compound A Benzyl Ester Pyriftalid Visual Weed Control (%) - 21 DAA
FIMMI
gae/ha gai/ha Obs Exp
4.38 0 20 -
0 45 50 -
0 90 30 -
4.38 45 100 60
4.38 90 90 44
ίο
CYPRO Cyperus rotundus L. nutsedge, purple
ECHCG Echinochloa crusgalli (L.) Beauv. bamyardgrass
ECHCO Echinochloa colona (L.) Link junglerice
FIMMI Fimbristylis miliacea (L.) Vahl fringerush, globe
LEFCH Leptochloa chinensis (L.) Nees sprangletop, Chinese
SCPMA Bolboschoenus maritimus (L.) Palla clubrush, sea •
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

Claims (13)

1. A synergistic herbicidal composition comprising a herbicidally effective amount of (a) a compound of the formula (I) or an agriculturally acceptable sait or ester thereof and (b) a dimethoxy-pyrimidine or an agriculturally acceptable sait, carboxylic acid, carboxylate sait, or ester thereof.
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: a pyrimidinylthiobenzoic acid and a pyrimidinyloxybenzoic acid.
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)
H,C'° ® or an agriculturally acceptable sait or ester thereof and (b) a dimethoxy-pyrimidine, or salts or esters thereof.
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 group consisting of: a pyrimidinylthiobenzoic acid and a pyrimidinyloxybenzoic acid.
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 claims 6-12, wherein the undesirable végétation comprises a herbicide résistant or tolérant weed.
OA1201500026 2012-07-24 2013-07-19 Herbicidal compositions comprising 4-amino3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3methoxyphenyl) pyridine-2-carboxylic acid. OA17277A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US61/675,117 2012-07-24
US61/675,109 2012-07-24
US13/833,362 2013-03-15

Publications (1)

Publication Number Publication Date
OA17277A true OA17277A (en) 2016-04-29

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