# Patent

## Title
Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl) pyridine-2-carboxylic acid or a derivative thereof and VLCFA and lipid synthesis inhibiting herbicides

## Abstract

A synergistic herbicidal composition containing (a) a compound of formula (I):




or an agriculturally acceptable salt or ester thereof and (b) VLCFA and fatty acid/lipid synthesis inhibiting herbicides, including but not limited to, acetochlor, alachlor, anilofos, benfuresate, cafenstrole, dimethenamid-P, fentrazamide, indanofan, flufenacet, mefenacet, s-metolachlor, molinate, pethoxamid, pretilachlor, prosulfocarb, pyroxasulfone, thenylchlor and thiobencarb, or a salt or ester thereof, provide synergistic weed control of undesirable vegetation in direct-seeded, water-seeded and transplanted rice, cereals, wheat, barley, oats, rye, sorghum, corn or maize, sugarcane, sunflower, oilseed rape, canola, sugar beet, soybean, cotton, pineapple, pastures, grasslands, rangelands, fallowland, turf, tree and vine orchards, aquatics, plantation crops, vegetables, industrial vegetation management (IVM) or rights-of-way (ROW).

## Background
PRIORITY CLAIM
This application claims the benefit of U.S. provisional patent application No. 61/675,105 filed on Jul. 24, 2012, this provisional application 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 salt thereof and (b) very long chain fatty acid (VLCFA) synthesis-inhibiting herbicides and fatty acid/lipid synthesis inhibiting herbicides.
Provided herein are also methods of controlling undesirable vegetation comprising applying (a) 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid or an agriculturally acceptable ester or salt thereof and (b) VLCFA and fatty acid/lipid synthesis inhibiting herbicides.
BACKGROUND
The protection of crops from weeds and other vegetation which inhibit crop growth is a constantly recurring problem in agriculture. To help combat this problem, researchers in the field of synthetic chemistry have produced an extensive variety of chemicals and chemical formulations effective in the control of such unwanted growth. Chemical herbicides of many types have 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 vegetation.
SUMMARY
Several embodiments are recited below. In the embodiments, the ratio of compound (a) to compound (b) can be expressed in terms of weight to weight (g to g), gae/ha to gae/ha, or gae/ha to gai/ha.
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 salt or ester thereof and (b) VLCFA and fatty acid/lipid synthesis inhibiting herbicides.

A second embodiment of the invention provided herein includes a method of controlling undesirable vegetation which comprises contacting the vegetation or the locus thereof with or applying to the soil or water to prevent the emergence or growth of vegetation the composition of embodiment 1.

A third embodiment of the invention provided herein includes a method of controlling undesirable vegetation which comprises contacting the vegetation or the locus thereof with or applying to the soil or water to prevent the emergence or growth of vegetation a herbicidally effective amount of (a) a compound of the formula (I)





or an agriculturally acceptable salt or ester thereof and (b) a VLCFA and fatty acid/lipid synthesis inhibiting herbicide.

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




or an agriculturally acceptable salt or ester of thereof, and (b) VLCFA and fatty acid/lipid synthesis inhibiting herbicides. Exemplary inhibiting herbicides include, but are not limited to, acetochlor, alachlor, anilofos, butachlor, benfuresate, cafenstrole, dimethenamid-P, fentrazamide, indanofan, flufenacet, mefenacet, s-metolachlor, molinate, pethoxamid, pretilachlor, prosulfocarb, pyroxasulfone, thenylchlor and thiobencarb, or acceptable salts and esters thereof. The compositions may also contain an agriculturally acceptable adjuvant or carrier.

Provided herein are also methods of controlling undesirable vegetation comprising applying (a) a compound of formula (I) or an agriculturally acceptable ester or salt thereof and (b) VLCFA and fatty acid/lipid synthesis inhibiting herbicides.


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




The compound of formula (I) can be identified by the name 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylic acid and has been described in U.S. Pat. No. 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 vegetation, including grass, broadleaf and sedge weeds, in multiple non-crop and cropping situations.

Exemplary VLCFA and fatty acid/lipid synthesis inhibiting herbicides include the chemical classes of acetamides, chloroacetamides, oxyacetamides, tetrazolinones, benzofuranes, thiocarbamates, and phosphorodithioates. Without being limited to any theory, their herbicidal activity is attributed to inhibition of very-long-chain fatty acid (VLCFA, fatty acids, e.g., >C18) synthesis and fatty acid/lipid synthesis. Exemplary VLCFA and fatty acid/lipid synthesis inhibiting herbicides include, but are not limited to acetochlor, alachlor, anilofos, butachlor, benfuresate, cafenstrole, dimethenamid-P, fentrazamide, indanofan, flufenacet, mefenacet, s-metolachlor, molinate, pethoxamid, pretilachlor, prosulfocarb, pyroxasulfone, thenylchlor and thiobencarb, or a salts thereof.
As used herein, acetochlor is 2-chloro-N-(ethoxymethyl)-N-(2-ethyl-6-methylphenyl)acetamide and possesses the following structure:




Its herbicidal activity is exemplified 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 of acetochlor include its use for pre-emergence or pre-plant control of grasses, certain broadleaf weeds and yellow nutsedge, e.g., in maize, soybeans, peanuts, cotton, potatoes and sugar cane.
As used herein, alachlor is 2-chloro-N-(2,6-diethylphenyl)-N-(methoxymethyl)acetamide and possesses the following structure:




Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of alachlor include its use for pre-emergence control of annual grasses and many broadleaf weeds, e.g., in cotton, brassica's, maize, oilseed rape, peanuts, radish, soybeans and sugar cane.
As used herein, anilofos is S-[2-[(4-chlorophenyl)(1-methylethyl)amino]-2-oxoethyl]O,O-dimethyl phosphorodithioate and possesses the following structure:




Its herbicidal activity is described in Journal of Applied Toxicology 2007, 27, 255-261. Exemplary uses of anilofos include, e.g., its use for control of annual grassy weeds and sedges, e.g., in transplanted rice.
As used herein, benfuresate is 2,3-dihydro-3,3-dimethyl-5-benzofuranyl ethanesulfonate and possesses the following structure:




Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of benfuresate include its use for post-emergence control of grass and broadleaf weeds, e.g., in paddy rice, fruit, beans, maize, sugar cane and perennial crops.
As used herein, butachlor is N-(butoxymethyl)-2-chloro-N-(2,6-diethylphenyl)acetamide and possesses the following structure:




Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of butachlor include its use for pre-emergence control of annual grasses and certain broadleaf weeds, e.g., in rice, both seeded and transplanted.
As used herein, cafenstrole is N,N-diethyl-3-[(2,4,6-trimethylphenyl)sulfonyl]-1H-1,2,4-triazole-1-carboxamide and possesses the following structure:




Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of cafenstrole include its use for pre- and post-emergence control of Echinochloa oryzicola, Cyperus difformis and other weeds, e.g., in paddy rice.
As used herein, dimethenamid is (RS)-2-chloro-N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-1-methylethyl)acetamide and possesses the following structure:




The S isomer, i.e., (S) 2-chloro-N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-1-methylethyl)acetamide has also been used as a herbicide. Herbicidal activity for dimethenamid is exemplified 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 of dimethenamid include its use for pre- or early post-emergence control of annual grass and broadleaf weeds, e.g., in maize, soybeans, sugar beet, potatoes, dry beans and other crops.

As used herein, fentrazamide is 4-(2-chlorophenyl)-N-cyclohexyl-N-ethyl-4,5-dihydro-5-oxo-1H-tetrazole-1-carboxamide and possesses the following structure:





Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of fentrazamide include its use for control of barnyard grass (Echinochloa spp.) and annual sedges, from weed pre-emergence, e.g., in rice.
As used herein, flufenacet is N-(4-fluorophenyl)-N-(1-methylethyl)-2-[[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]oxy]acetamide and possesses the following structure:




Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of flufenacet include its use for broad-spectrum grass control and control of broadleaf weeds.
As used herein, indanofan is (RS)-2-[[2-(3-chlorophenyl)oxiranyl]methyl]-2-ethyl-1H-indene-1,3(2H)-dione and possesses the following structure:




Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of indanofan include its use for pre-emergence and post-emergence weed control, e.g., in transplanted rice, and pre-emergence weed control in turf.
As used herein, mefenacet is 2-(2-benzothiazolyloxy)-N-methyl-N-phenylacetamide and possesses the following structure:




Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of mefenacet include its use for pre-emergence and early post-emergence control of grass weeds, e.g., in transplanted rice.
As used herein, S-metolachlor is a mixture of 2-chloro-N-(2-ethyl-6-methylphenyl)-N-[(1S)-2-methoxy-1-methyl ethyl]acetamide and 2-chloro-N-(2-ethyl-6-methylphenyl)-N-[(1R)-2-methoxy-1-methylethyl]acetamide, wherein the mixture contains predominantly S-isomer, e.g., 80-100%. Metolachlor has the following formula:




Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of S-metolachlor include its use for control of annual grasses and broadleaf weeds, e.g., in maize, sorghum, cotton, sugar beet, fodder beet, sugar cane, potatoes, peanuts, soybeans, safflowers, sunflowers, various vegetables, fruit and nut trees, and woody ornamentals.
As used herein, molinate is S-ethyl hexahydro-1H-azepine-1-carbothioate and possesses the following structure:




Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of molinate include its use for control of germinating broadleaf and grass weeds, e.g., in rice.
As used herein, pethoxamid is 2-Chloro-N-(2-ethoxyethyl)-N-(2-methyl-1-phenyl-1-propen-1-yl)acetamide and possesses the following structure:




Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of pethoxamid include its use for pre-emergence to early post-emergence control of Echinochloa, Digitaria, Setaria, Amaranthus and Chenopodium spp., and other monocotyledonous and annual broadleaf weeds, e.g., in corn/maize, oilseed rape and soybeans.
As used herein, pretilachlor is 2-chloro-N-(2,6-diethylphenyl)-N-(2-propoxyethyl)acetamide and possesses the following structure:




Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of pretilachlor include its use for control of annual grasses, broadleaf weeds and sedges, e.g., in transplanted and seeded rice.
As used herein, prosulfocarb is S-(phenylmethyl) dipropylcarbamothioate and possesses the following structure:




Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of prosulfocarb include its use for pre- and early post-emergence control of grass and broadleaf weeds, e.g., in winter wheat, winter barley and rye.
As used herein, pyroxasulfone is 3-[[[5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl]sulfonyl]-4,5-dihydro-5,5-dimethylisoxazole and possesses the following structure:




Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Pyroxasulfone provides, e.g., pre-emergence control of annual grasses and some broadleaf weeds in maize, soybeans, wheat and other crops.
As used herein, thenylchlor is 2-chloro-N-(2,6-dimethylphenyl)-N-[(3-methoxy-2-thienyl)methyl]acetamide and possesses the following structure:




Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of thenylchlor include its use for pre-emergence control of annual grass and broadleaf weeds, e.g., in paddy rice.
As used herein, thiobencarb is S-[(4-chlorophenyl)methyl]N,N-diethylcarbamothioate and possesses the following structure:




Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of thiobencarb include its use for pre-emergence to early post-emergence control of Echinochloa, Leptochloa and Cyperus spp., and other monocotyledonous and annual broadleaf weeds, e.g., in direct-seeded and transplanted rice.
As used herein, herbicide means a compound, e.g., active ingredient that kills, controls or otherwise adversely modifies the growth of plants.
As used herein, a herbicidally effective or vegetation controlling amount is an amount of active ingredient which causes an adversely modifying effect to the vegetation e.g., causing deviations from natural development, killing, effecting regulation, causing desiccation, causing retardation, and the like.
As used herein, controlling undesirable vegetation means preventing, reducing, killing, or otherwise adversely modifying the development of plants and vegetation. Described herein are methods of controlling undesirable vegetation through the application of certain herbicide combinations or compositions. Methods of application include, but are not limited to applications to the vegetation or locus thereof, e.g., application to the area adjacent to the vegetation, 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 vegetation, 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 vegetation include, but are not limited to, germinant seeds, emerging seedlings, plants emerging from vegetative propagules, immature vegetation, and established vegetation.
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 include those derived from alkali or alkaline earth metals and those derived from ammonia and amines. Exemplary cations include sodium, potassium, magnesium, and aminium cations of the formula:

R1R2R3R4N+

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

Exemplary esters include those derived from C1-C12 alkyl, C3-C12 alkenyl, C3-C12 alkynyl or C7-C10 aryl-substituted alkyl alcohols, such as methyl alcohol, isopropyl alcohol, 1-butanol, 2-ethylhexanol, butoxyethanol, methoxypropanol, allyl alcohol, propargyl alcohol, cyclohexanol or unsubstituted or substituted benzyl alcohols. Benzyl alcohols may be substituted with from 1-3 substituents independently selected from halogen, C1-C4 alkyl or C1-C4 alkoxy. Esters can be prepared by coupling of the acids with the alcohol using any number of 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 or by transesterification.
Compositions and Methods
Provided herein are herbicidal compositions comprising a herbicidally effective amount of (a) a compound of the formula (I)




or an agriculturally acceptable salt or ester of thereof, and (b) VLCFA and fatty acid/lipid synthesis inhibiting herbicides. In some embodiments, the VLCFA and fatty acid/lipid synthesis inhibiting herbicide is acetochlor, alachlor, anilofos, butachlor, benfuresate, cafenstrole, dimethenamid, fentrazamide, indanofan, flufenacet, mefenacet, s-metolachlor, molinate, pethoxamid, pretilachlor, prosulfocarb, pyroxasulfone, thenylchlor and thiobencarb, or a salt thereof.

Provided herein are also methods of controlling undesirable vegetation comprising contacting the vegetation or the locus thereof, i.e., the area adjacent to the vegetation with or applying to the soil or water to prevent the emergence or growth of vegetation a herbicidally effective amount of the compound of formula (I) or salt of ester thereof and (b) VLCFA and fatty acid/lipid synthesis inhibiting herbicides. In certain embodiments, the methods employ the compositions described herein.
Furthermore, in some embodiments, the combination of compound (I) or agriculturally acceptable salt or ester thereof and VLCFA and fatty acid/lipid synthesis inhibiting herbicides, or an agriculturally acceptable salt or ester thereof exhibits synergism, e.g., the herbicidal active ingredients 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 equation. Colby, S. R. 1967. Calculation of the synergistic and antagonistic response of herbicide combinations. Weeds 15:20-22.
In certain embodiments of the compositions and methods described herein, the compound of formula (I), i.e., the carboxylic acid, is employed. In certain embodiments, a carboxylate salt 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 C1-4 alkyl, e.g., n-butyl ester is employed. In certain embodiments, the benzyl ester is employed.
In some embodiments, the compound of formula (I) or salt or ester thereof and acetochlor, alachlor, anilofos, butachlor, benfuresate, cafenstrole, dimethenamid, fentrazamide, indanofan, flufenacet, mefenacet, s-metolachlor, molinate, pethoxamid, pretilachlor, prosulfocarb, pyroxasulfone, thenylchlor and thiobencarb, or an agriculturally acceptable salt thereof are formulated in one composition, tank mixed, applied simultaneously, or applied sequentially.
Herbicidal activity is exhibited by the compounds when they are applied directly to the plant or to the locus of the plant at any stage of growth. The effect observed depends 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 specific compound employed, the specific 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 selective 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 vegetation 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, corn/maize, sugarcane, sunflower, oilseed rape, canola, sugar beet, soybean, cotton, pineapple, pastures, grasslands, rangelands, fallowland, turf, tree and vine orchards, aquatics, plantation crops, vegetables, industrial vegetation management (IVM) and rights-of-way (ROW).
In certain embodiments, the compositions and methods provided herein are utilized to control weeds in rice. In certain embodiments, the rice is direct-seeded, water-seeded, or transplanted rice.
The compositions and methods described herein may be used to control undesirable vegetation in glyphosate-tolerant-, 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitor-tolerant-, glufosinate-tolerant-, glutamine synthetase inhibitor-tolerant-, dicamba-tolerant-, phenoxy auxin-tolerant-, pyridyloxy auxin-tolerant-, auxin-tolerant-, auxin transport inhibitor-tolerant-, aryloxyphenoxypropionate-tolerant-, cyclohexanedione-tolerant-, phenylpyrazoline-tolerant-, acetyl CoA carboxylase (ACCase) inhibitor-tolerant-, imidazolinone-tolerant-, sulfonylurea-tolerant-, pyrimidinylthiobenzoate-tolerant-, triazolopyrimidine-tolerant-, sulfonylaminocarbonyltriazolinone-tolerant-, acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitor-tolerant-, 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor-tolerant-, phytoene desaturase inhibitor-tolerant-, carotenoid biosynthesis inhibitor-tolerant-, protoporphyrinogen oxidase (PPO) inhibitor-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-, bromoxynil-tolerant-crops (such as, but not limited to, soybean, cotton, canola/oilseed rape, 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 vegetation in crops possessing multiple or stacked traits conferring tolerance to multiple chemistries and/or inhibitors of multiple modes of action. In some embodiments, the compound of formula (I) or salt or ester thereof and complementary herbicide or salt or ester thereof are used in combination with herbicides that are selective for the crop being treated and which complement 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 sequentially.
The compositions and methods may be used in controlling undesirable vegetation in crops possessing agronomic stress tolerance (including but not limited to drought, cold, heat, salt, water, nutrient, fertility, pH), pest tolerance (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 vegetation. Undesirable vegetation includes, but is not limited to, undesirable vegetation that occurs in direct-seeded, water-seeded, and transplanted rice, cereals, wheat, barley, oats, rye, sorghum, corn/maize, sugarcane, sunflower, oilseed rape, canola, sugar beet, soybean, cotton, pineapple, pastures, grasslands, rangelands, fallowland, turf, tree and vine orchards, ornamental species, aquatics, plantation crops, vegetables, industrial vegetation management (IVM) and rights of way (ROW).
In some embodiments, the methods provided herein are utilized to control undesirable vegetation in rice. In certain embodiments, the undesirable vegetation is Brachiaria platyphylla (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. (barnyardgrass, 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 barnyardgrass, 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), Alternanthera philoxeroides (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 (morningglories, IPOSS), Ipomoea hederacea (L.) Jacq. (ivyleaf morningglory, IPOHE), Lindernia dubia (L.) Pennell (low false pimpernel, LIDDU), Ludwigia species (LUDSS), Ludwigia linifolia Poir. (southeastern primrose-willow, LUDLI), Ludwigia octovalvis (Jacq.) Raven (longfruited primrose-willow, LUDOC), Monochoria korsakowii Regel & Maack (monochoria, MOOKA), Monochoria vaginalis (Burm. F.) C. Presl ex Kuhth, (monochoria, MOOVA), Murdannia nudiflora (L.) Brenan (doveweed, MUDNU), Polygonum pensylvanicum L., (Pennsylvania smartweed, POLPY), Polygonum persicaria L. (ladysthumb, POLPE), Polygonum hydropiperoides Michx. (POLHP, mild smartweed), Rotala indica (Willd.) Koehne (Indian toothcup, ROTIN), Sagittaria species, (arrowhead, SAGSS), Sesbania exaltata (Raf.) Cory/Rydb. Ex Hill (hemp sesbania, SEBEX), or Sphenoclea zeylanica Gaertn. (gooseweed, SPDZE).
In some embodiments, the methods provided herein are utilized to control undesirable vegetation in cereals. In certain embodiments, the undesirable vegetation 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 multflorum Lam. (Italian ryegrass, LOLMU), Phalaris minor Retz. (littleseed canarygrass, PHAMI), Poa annua L. (annual bluegrass, POANN), Setaria pumila (Poir.) Roemer & J. A. Schultes (yellow foxtail, SETLU), Setaria viridis (L.) Beauv. (green foxtail, SETVI), Amaranthus retroflexus L. (redroot pigweed, AMARE), Brassica species (BRSSS), Chenopodium album L. (common lambsquarters, CHEAL), Cirsium arvense (L.) Scop. (Canada thistle, CIRAR), Galium aparine L. (catchweed bedstraw, GALAP), Kochia scoparia (L.) Schrad. (kochia, KCHSC), Lamium purpureum L. (purple deadnettle, LAMPU), Matricaria recutita L. (wild chamomile, MATCH), Matricaria matricarioides (Less.) Porter (pineappleweed, MATMT), Papaver rhoeas L. (common poppy, PAPRH), Polygonum convolvulus L. (wild buckwheat, POLCO), Salsola tragus L. (Russian thistle, SASKR), Sinapis species (SINSS), Sinapis arvensis L. (wild mustard, SINAR), Stellaria media (L.) Vill. (common chickweed, STEME), Veronica persica Poir. (Persian speedwell, VERPE), Viola arvensis Murr. (field violet, VIOAR), or Viola tricolor L. (wild violet, VIOTR).
In some embodiments, the methods provided herein are utilized to control undesirable vegetation in range and pasture, fallowland, IVM and ROW. In certain embodiments, the undesirable vegetation 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./Torn. (prickly lettuce, LACSE), Plantago lanceolata L. (buckhorn 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 vegetation found in row crops, tree and vine crops and perennial crops. In certain embodiments, the undesirable vegetation is Alopecurus myosuroides Huds. (blackgrass, ALOMY), Avena fatua L. (wild oat, AVEFA), Brachiaria decumbens Stapf. or Urochloa decumbens (Stapf) R. D. Webster (Surinam grass, BRADC), Brachiaria brizantha (Hochst. ex A. Rich.) Stapf. or Urochloa brizantha (Hochst. ex A. Rich.) R. D. (beard grass, BRABR), Brachiaria platyphylla (Groseb.) Nash or Urochloa platyphylla (Nash) R. D. Webster (broadleaf signalgrass, BRAPP), Brachiaria plantaginea (Link) Hitchc. or Urochloa plantaginea (Link) R. D. Webster (alexandergrass, BRAPL), Cenchrus echinatus L. (southern sandbar, 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. (barnyardgrass, ECHCG), Echinochloa colonum (L.) Link (junglerice, ECHCO), Eleusine indica (L.) Gaertn. (goosegrass, ELEIN), Lolium multiflorum 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), Bidens pilosa 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 carrot, DAUCA), Euphorbia heterophylla L. (wild poinsettia, EPHHL), Euphorbia hirta L. or Chamaesyce hirta (L.) Millsp. (garden spurge, EPHHI), Euphorbia dentata Michx. (toothed spurge, EPHDE), Erigeron bonariensis L. or Conyza bonariensis (L.) Cronq. (hairy fleabane, ERIBO), Erigeron canadensis L. or Conyza canadensis (L.) Cronq. (Canadian fleabane, ERICA), Conyza sumatrensis (Retz.) E. H. Walker (tall fleabane, ERIFL), Helianthus annuus L. (common sunflower, HELAN), Jacquemontia tamnifolia (L.) Griseb. (smallflower morningglory, IAQTA), Ipomoea hederacea (L.) Jacq. (ivyleaf morningglory, IPOHE), Ipomoea lacunosa L. (white morningglory, IPOLA), Lactuca serriola L./Torn. (prickly lettuce, LACSE), Portulaca oleracea L. (common purslane, POROL), Richardia species (pusley, RCHSS), Sida species (sida, SIDSS), Sida spinosa L. (prickly sida, SIDSP), Sinapis arvensis L. (wild mustard, SINAR), Solanum ptychanthum Dunal (eastern black nightshade, SOLPT), Tridax procumbens L. (coat buttons, TRQPR), or Xanthium strumarium L. (common cocklebur, XANST).
In some embodiments, the methods provided herein are utilized to control undesirable vegetation in turf. In certain embodiments, the undesirable vegetation is Bellis perennis L. (English daisy, BELPE), Cyperus esculentus L. (yellow nutsedge, CYPES), Cyperus species (CYPSS), Digitaria sanguinalis (L.) Scop. (large crabgrass, DIGSA), Diodia virginiana L. (Virginia buttonweed, DIQVI), Euphorbia species (spurge, EPHSS), Glechoma hederacea L. (ground ivy, GLEHE), Hydrocotyle umbellata L. (dollarweed, HYDUM), Kylling a 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. (buckhorn/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 vegetation consisting of grass, broadleaf and sedge weeds. In certain embodiments, the compositions and methods provided herein are utilized to control undesirable vegetation including Bolboschoenus, Brachiaria, Chenopodium, Cirsium, Cyperus, Digitaria, Echinochloa, Fimbristylis, Galium, Ipomoea, Ischaemum, Kochia, Leptochloa, Papaver, Polygonum, Salsola, Schoenoplectus, Sinapis, Stellaria and Xanthium. 
In some embodiments, the combination of compound (I) or agriculturally acceptable ester or salt thereof and VLCFA and fatty acid/lipid synthesis inhibiting herbicides or agriculturally acceptable salt or ester thereof is used to control Brachiaria platyphylla (Griseb.) Nash, or Urochloa platyphylla (Nash) R. D. Webster (broadleaf signalgrass, BRAPP), Cyperus esculentus L. (yellow nutsedge, CYPES), Cyperus iria L. (rice flatsedge, CYPIR), Cyperus rotundus L. (purple nutsedge, CYPRO), Digitaria sanguinalis (L.) Scop. (large crabgrass, DIGSA), Echinochloa crus-galli (L.) Beauv. (barnyardgrass, ECHCG), Echinochloa colona (L.) Link, (junglerice, ECHCO), Echinochloa oryzoides (Ard.) Fritsch (early watergrass, ECHOR), Fimbristylis miliacea (L.) Vahl (globe fringerush, FIMMI), Galium aparine L. (catchweed bedstraw, GALAP), Ipomoea hederacea Jacq. (ivyleaf morningglory, IPOHE), Ischaemum rugosum Salisb. (saramollagrass, ISCRU), Kochia scoparia (L.) Schrad. (kochia, KCHSC), Leptochloa chinensis (L.) Nees (Chinese sprangletop, LEFCH) Papaver rhoeas L. (common poppy, PAPRH), Polygonum hydropiperoides Michx. (POLHP, mild smartweed), Salsola tragus L. (Russian thistle, SASKR), Schoenoplectus juncoides (Roxb.) Palla (Japanese bulrush, SCPJU), Sinapis arvensis L. (wild mustard, SINAR), Stellaria media (L.) Vill. (common chickweed, STEME) and Xanthium strumarium L. (common cocklebur, XANST).
The compounds of formula I or agriculturally acceptable salt or ester thereof may be used to control herbicide resistant or tolerant weeds. The methods employing the combination of a compound of formula I or agriculturally acceptable salt or ester thereof and the compositions described herein may also be employed to control herbicide resistant or tolerant weeds. Exemplary resistant or tolerant weeds include, but are not limited to, biotypes resistant or tolerant to acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors (e.g., imidazolinones, sulfonylureas, pyrimidinylthiobenzoates, triazolopyrimidines, sulfonylaminocarbonyltriazolinones), photosystem II inhibitors (e.g., phenylcarbamates, pyridazinones, triazines, triazinones, uracils, amides, ureas, benzothiadiazinones, nitriles, phenylpyridazines), acetyl CoA carboxylase (ACCase) inhibitors (e.g., aryloxyphenoxypropionates, cyclohexanediones, phenylpyrazolines), synthetic auxins, (e.g., benzoic acids, phenoxycarboxylic acids, pyridine carboxylic acids, quinoline carboxylic acids), auxin transport inhibitors (e.g., phthalamates, semicarbazones), photosystem I inhibitors (e.g., bipyridyliums), 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors (e.g., glyphosate), glutamine synthetase inhibitors (e.g., glufosinate, bialafos), microtubule assembly inhibitors (e.g., benzamides, benzoic acids, dinitroanilines, phosphoramidates, pyridines), mitosis inhibitors (e.g., carbamates), very long chain fatty acid (VLCFA) inhibitors (e.g., acetamides, chloroacetamides, oxyacetamides, tetrazolinones), fatty acid and lipid synthesis inhibitors (e.g., phosphorodithioates, thiocarbamates, benzofuranes, chlorocarbonic acids), protoporphyrinogen oxidase (PPO) inhibitors (e.g., diphenylethers, N-phenylphthalimides, oxadiazoles, oxazolidinediones, phenylpyrazoles, pyrimidindiones, thiadiazoles, triazolinones), carotenoid biosynthesis inhibitors (e.g., clomazone, amitrole, aclonifen), inhibitors, 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), mitosis inhibitors, 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 resistant or tolerant weeds include, but are not limited to, biotypes with resistance or tolerance to multiple herbicides, biotypes with resistance or tolerance to multiple chemical classes, biotypes with resistance or tolerance to multiple herbicide modes-of-action, and biotypes with multiple resistance or tolerance mechanisms (e.g., target site resistance or metabolic resistance).
In some embodiments, an agriculturally acceptable salt of acetochlor, alachlor, anilofos, butachlor, benfuresate, cafenstrole, dimethenamid-P, fentrazamide, indanofan, flufenacet, mefenacet, s-metolachlor, molinate, pethoxamid, pretilachlor, prosulfocarb, pyroxasulfone, thenylchlor and thiobencarb is employed in the methods or compositions described herein.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with acetochlor. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to acetochlor is within the range of from about 1:1680 to about 6:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to acetochlor is within the range of from about 1:46 to about 1:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to acetochlor is within the range of from about 1:90 to about 1:2. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to acetochlor is within the range of from about 1:46 to about 1:5.5. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl ester and acetochlor. In one embodiment, the composition comprises the compound of formula (I) and acetochlor, wherein the weight ratio of the compound of formula (I) to acetochlor is about 1:46 to about 1:5.5. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and acetochlor, wherein the weight ratio of the benzyl ester of the compound of formula (I) to acetochlor is about 1:23 to about 1:5.5. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 52 grams active ingredient per hectare (gai/ha) to about 3,660 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 54 grams active ingredient per hectare (gai/ha) to about 235 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and acetochlor, e.g., sequentially or simultaneously. In some embodiments, the acetochlor is applied at a rate from about 50 gai/ha to about 3360 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 grams acid equivalent per hectare (gae/ha) to about 300 gae/ha. In some embodiments, the acetochlor is applied at a rate from about 50 gai/ha to about 400 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 g acid equivalent per hectare (gae/ha) to about 45 gae/ha. In some embodiments, the acetochlor is applied at a rate from about 100 gai/ha to about 200 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha. In certain embodiments, the methods utilize the compound of formula (I), or its benzyl ester and acetochlor. In one embodiment, the methods utilize the compound of formula (I) and acetochlor, wherein the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 35 gae/ha, and acetochlor is applied at a rate of about 50 gai/ha to about 200 gai/ha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and acetochlor, wherein the benzyl ester of the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 35 gae/ha, and acetochlor is applied at a rate of about 50 gai/ha to about 200 gai/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with acetochlor are used to control BRAPP, DIGSA, ECHCG, ECHOR, CYPRO, LEFCH or FIMMI.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with alachlor. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to alachlor is within the range of from about 1:3350 to about 2:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to alachloror salt or ester thereof is within the range of from about 1:1000 to about 1:3. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to alachloror salt or ester thereof is within the range of from about 1:39 to about 1:78. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and alachlor. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 172 grams active ingredient per hectare (gai/ha) to about 7000 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 174 grams active ingredient per hectare (gai/ha) to about 2290 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 1272 grams active ingredient per hectare (gai/ha) to about 2512 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and alachlor, e.g., sequentially or simultaneously. In some embodiments, the alachlor is applied at a rate from about 170 gai/ha to about 6700 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and alachlor. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with alachlor are used to control IPOHE.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with anilofos. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to anilofos or salt or ester thereof is within the range of from about 1:250 to about 1.5:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to anilofos is within the range of from about 1:45 to about 1:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to anilofos is within the range of from about 1:50 to about 1:3. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and anilofos. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 52 grams active ingredient per hectare (gai/ha) to about 750 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 54 grams active ingredient per hectare (gai/ha) to about 235 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and anilofos, e.g., sequentially or simultaneously. In some embodiments, the anilofos is applied at a rate from about 50 gai/ha to about 450 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the anilofos is applied at a rate from about 100 gai/ha to about 400 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 8 gae/ha to about 32 gae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and anilofos. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with aniliphos are used to control ECHCG, ECHOR, CYPRO or FIMMI.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with benfuresate. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to benfuresate is within the range of from about 1:150 to about 2:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to benfuresate is within the range of from about 1:113 to about 1.33:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to benfuresate is within the range of from about 1:70 to about 1:1 In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to benfuresate is within the range of from about 1:70 to about 1:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to benfuresate is within the range of from about 1:36 to about 1:1.8. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl ester and benfuresate. In one embodiment, the composition comprises the compound of formula (I) and benfuresate, wherein the weight ratio of the compound of formula (I) to benfuresate is about 1:36 to about 1:1.8. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and benfuresate, wherein the weight ratio of the benzyl ester of the compound of formula (I) to benfuresate is about 1:36 to about 1:2. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 52 grams active ingredient per hectare (gai/ha) to about 600 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 55 grams active ingredient per hectare (gai/ha) to about 242 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and benfuresate or salt or ester thereof, e.g., sequentially or simultaneously. In some embodiments, benfuresate is applied at a rate from about 50 gai/ha to about 300 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the benfuresate is applied at a rate from about 25 gai/ha to about 1200 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 g acid equivalent per hectare (gae/ha) to about 200 gae/ha. In some embodiments, the benfuresate is applied at a rate from about 50 gai/ha to about 600 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 5.3 g acid equivalent per hectare (gae/ha) to about 100 gae/ha. In certain embodiments, the methods utilize the compound of formula (I), or its benzyl ester and benfuresate. In one embodiment, the methods utilize the compound of formula (I) and benfuresate, wherein the compound of formula (I) is applied at a rate of from about 5.3 g acid equivalent per hectare (gae/ha) to about 42.4 gae/ha, and benfuresate is applied at a rate of about 50 gai/ha to about 200 gai/ha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and benfuresate, wherein the benzyl ester of the compound of formula (I) is applied at a rate of from about 5.3 g acid equivalent per hectare (gae/ha) to about 100 gae/ha, and benfuresate is applied at a rate of about 50 gai/ha to about 600 gai/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with benfuresate are used to control ECHCG, ECHCO, LEFCH, CYPIR, POLHP, SCPJU or ECHOR.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with butachlor. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to butachlor is within the range of from about 1:750 to about 3:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to butachlor is within the range of from about 1:103 to about 1:6. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to butachlor is within the range of from about 1:200 to about 1:3. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to butachlor is within the range of from about 1:102 to about 1:6. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl or n-butyl ester and butachlor. In one embodiment, the composition comprises the compound of formula (I) and butachlor, wherein the weight ratio of the compound of formula (I) to butachlor is about 1:102 to about 1:6. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and butachlor, wherein the weight ratio of the benzyl ester of the compound of formula (I) to butachlor is about 1:102 to about 1:6. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 115 grams active ingredient per hectare (gai/ha) to about 1800 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 117 grams acid active ingredient per hectare (gai/ha) to about 468 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and butachlor, e.g., sequentially or simultaneously. In some embodiments, the butachlor is applied at a rate from about 113 gai/ha to about 1500 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the butachloror salt or ester thereof is applied at a rate from about 50 gai/ha to about 900 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 g acid equivalent per hectare (gae/ha) to about 45 gae/ha. In some embodiments, the butachloror salt or ester thereof is applied at a rate from about 112.5 gai/ha to about 450 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha. In certain embodiments, the methods utilize the compound of formula (I), or its benzyl or n-butyl ester and butachlor. In one embodiment, the methods utilize the compound of formula (I) and butachlor, wherein the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 35 gae/ha, and butachlor is applied at a rate of about 112.5 gai/ha to about 450 gai/ha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and butachlor, wherein the benzyl ester of the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 35 gae/ha, and butachlor is applied at a rate of about 112.5 gai/ha to about 450 gai/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with butachlor are used to control ECHCO, LEFCH, BRAPP, IPOHE, ECHCG, ECHOR, or CYPRO.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with cafenstrole. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to cafenstrole is within the range of from about 1:150 to about 2:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to cafenstrole is within the range of from about 1:24 to about 1:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to cafenstrole is within the range of from about 1:50 to about 2:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to cafenstrole is within the range of from about 1:24 to about 1:1.5. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl ester and cafenstrole. In one embodiment, the composition comprises the compound of formula (I) and cafenstrole, wherein the weight ratio of the compound of formula (I) to cafenstrole is about 1:24 to about 1:1.5. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and cafenstrole, wherein the weight ratio of the benzyl ester of the compound of formula (I) to cafenstrole is about 1:24 to about 1:1.5. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and cafenstrole, wherein the weight ratio of the benzyl ester of the compound of formula (I) to cafenstrole is about 1:47 to about 2.7:1. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 28 grams active ingredient per hectare (gai/ha) to about 600 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 30 grams active ingredient per hectare (gai/ha) to about 150 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and cafenstrole, e.g., sequentially or simultaneously. In some embodiments, the cafenstrole is applied at a rate from about 26 gai/ha to about 300 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the cafenstrole is applied at a rate from about 10 gai/ha to about 200 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 g acid equivalent per hectare (gae/ha) to about 45 gae/ha. In some embodiments, the cafenstrole is applied at a rate from about 26.3 gai/ha to about 105 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha. In certain embodiments, the methods utilize the compound of formula (I), or its benzyl ester and cafenstrole. In one embodiment, the methods utilize the compound of formula (I) and cafenstrole, wherein the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha, and cafenstrole is applied at a rate of about 26.3 gai/ha to about 105 gai/ha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and cafenstrole, wherein the benzyl ester of the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha, and cafenstrole is applied at a rate of about 26.3 gai/ha to about 105 gai/ha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and cafenstrole, wherein the benzyl ester of the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 70 gae/ha, and cafenstrole is applied at a rate of about 26.3 gai/ha to about 210 gai/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with cafenstrole are used to control BRAPP, ECHCG, ECHCO, LEFCH, IPOHE, CYPIR, ECHOR, SCPJU or CYPRO.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with dimethenamid-P. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to dimethenamid-P is within the range of from about 1:850 to about 1:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to dimethenamid-P is within the range of from about 1:205 to about 1:8. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and dimethenamid-P. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 282 grams active ingredient per hectare (gai/ha) to about 2,000 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 283 grams active ingredient per hectare (gai/ha) to about 1,670 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and dimethenamid-P, e.g., sequentially or simultaneously. In some embodiments, the dimethenamid-P is applied at a rate from about 280 gai/ha to about 1,700 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the dimethenamid-P is applied at a rate from about 275 gai/ha to about 1,640 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 8 gae/ha to about 32 gae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and dimethenamid-P are used to control ECHCO and XANST.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with fentrazamide. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to fentrazamide 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 salt or ester thereof to fentrazamide is within the range of from about 1:15 to about 1:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to fentrazamide is within the range of from about 1:68 to about 2:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to fentrazamide is within the range of from about 1:32 to about 2:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to fentrazamide is within the range of from about 1:16 to about 1:1.5. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl ester and fentrazamide. In one embodiment, the composition comprises the compound of formula (I) and fentrazamide, wherein the weight ratio of the compound of formula (I) to fentrazamide is about 1:16 to about 1:1.5. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and fentrazamide, wherein the weight ratio of the benzyl ester of the compound of formula (I) to fentrazamide is about 1:8 to about 1:2. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 18 grams active ingredient per hectare (gai/ha) to about 600 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 20 grams active ingredient per hectare (gai/ha) to about 150 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and fentrazamide, e.g., sequentially or simultaneously. In some embodiments, fentrazamide is applied at a rate from about 16 gai/ha to about 300 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the fentrazamide is applied at a rate from about 7 gai/ha to about 140 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 g acid equivalent per hectare (gae/ha) to about 45 gae/ha. In some embodiments, the fentrazamide is applied at a rate from about 16.9 gai/ha to about 67.5 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha. In certain embodiments, the methods utilize the compound of formula (I), or its benzyl ester and fentrazamide. In one embodiment, the methods utilize the compound of formula (I) and fentrazamide, wherein the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha, and fentrazamide is applied at a rate of about 16.9 gai/ha to about 67.5 gai/ha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and fentrazamide, wherein the benzyl ester of the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 35 gae/ha, and fentrazamide is applied at a rate of about 33.8 gai/ha to about 300 gai/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with fentrazamide are used to control BRAPP, ECHCG, ECHCO, LEFCH, DIGSA, or ECHOR.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with flufenacet. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to flufenacet is within the range of from about 1:125 to about 12:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to flufenacet is within the range of from about 1:68 to about 6:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to flufenacet is within the range of from about 1:300 to about 1:2. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and flufenacet. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 27 grams active ingredient per hectare (gai/ha) to about 550 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the composition is applied at an application rate of from about 62 grams active ingredient per hectare (gai/ha) to about 800 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 28 grams active ingredient per hectare (gai/ha) to about 300 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and flufenacet, e.g., sequentially or simultaneously. In some embodiments, the flufenacet is applied at a rate from about 25 gai/ha to about 1,250 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the flufenacet is applied at a rate from about 60 gai/ha to about 750 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 8 gae/ha to about 32 gae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and flufenacet. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with flufenacet are used to control BRAPP, CIRAR, CHEAL, KCHSC, PAPRH, SASKR, SINAR and STEME
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with indanofan. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to indanofan is within the range of from about 1:150 to about 12:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to indanofan is within the range of from about 1:136 to about 6:1. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and indanofan. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 27 grams active ingredient per hectare (gai/ha) to about 600 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 30 grams acid active ingredient per hectare (gai/ha) to about 450 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and indanofan, e.g., sequentially or simultaneously. In some embodiments, the indanofan is applied at a rate from about 25 gai/ha to about 300 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the indanofan is applied at a rate from about 37.5 gai/ha to about 150 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 8 gae/ha to about 32 gae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and indanofan. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with indanofan are used to control ECHCO and LEFCH.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with mefenacet. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to mefenacet is within the range of from about 1:800 to about 1:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to mefenacet is within the range of from about 1:727 to about 1:2. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to mefenacet is within the range of from about 1:150 to about 1:2. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and mefenacet. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 252 grams active ingredient per hectare (gai/ha) to about 1900 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 255 grams acid active ingredient per hectare (gai/ha) to about 1750 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and mefenacet or salt thereof, e.g., sequentially or simultaneously. In some embodiments, the mefenacet is applied at a rate from about 250 gai/ha to about 1600 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the mefenacet is applied at a rate from about 50 gai/ha to about 1200 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 8 gae/ha to about 32 gae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and mefenacet. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with mefenacet are used to control BRAPP, LEFCH, CYPIR or ECHOR.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with s-metolachlor. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to s-metolachlor is within the range of from about 1:1500 to about 4:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to s-metolachlor is within the range of from about 1:1000 to about 1:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to s-metolachlor is within the range of from about 1:194 to about 1:12. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and s-metolachlor. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 72 grams active ingredient per hectare (gai/ha) to about 3300 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 73 grams active ingredient per hectare (gai/ha) to about 2290 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and s-metolachlor, e.g., sequentially or simultaneously. In some embodiments, the s-metolachlor is applied at a rate from about 70 gai/ha to about 3000 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the s-metolachlor is applied at a rate from about 387 gai/ha to about 1550 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 8 gae/ha to about 32 gae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and s-metolachlor. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with s-metolachlor are used to control ECHCG or IPOHE.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with molinate. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to molinate is within the range of from about 1:2780 to about 1:4. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to molinate is within the range of from about 1:255 to about 1:8. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to molinate is within the range of from about 1:194 to about 1:44. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and molinate. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 282 grams active ingredient per hectare (gai/ha) to about 5860 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 284 grams active ingredient per hectare (gai/ha) to about 1155 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 1408 grams active ingredient per hectare (gai/ha) to about 2832 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and molinate, e.g., sequentially or simultaneously. In some embodiments, the molinate is applied at a rate from about 280 gai/ha to about 5560 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the molinate is applied at a rate from about 1400 gai/ha to about 2800 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 8 gae/ha to about 32 gae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and molinate. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with s-molinate are used to control ECHOR.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with pethoxamid. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to pethoxamid is within the range of from about 1:625 to about 1:10. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to pethoxamid is within the range of from about 1:150 to about 1:38. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and pethoxamid. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 202 grams active ingredient per hectare (gai/ha) to about 1,550 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 313 grams acid active ingredient per hectare (gai/ha) to about 1,252 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and pethoxamid, e.g., sequentially or simultaneously. In some embodiments, the pethoxamid is applied at a rate from about 200 gai/ha to about 1,250 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the pethoxamid is applied at a rate from about 305 gai/ha to about 1,220 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 8 gae/ha to about 32 gae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester in combination with pethoxamid are used to control LEFCH, CYPRO or CYPIR.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with pretilachlor. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to pretilachlor is within the range of from about 1:375 to about 2:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to pretilachlor is within the range of from about 1:34 to about 1:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to pretilachlor is within the range of from about 1:64 to about 1:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to pretilachlor is within the range of from about 1:32 to about 1:2. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to pretilachlor is within the range of from about 1:91 to about 2.7:1. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl ester and pretilachlor. In one embodiment, the composition comprises the compound of formula (I) and pretilachlor, wherein the weight ratio of the compound of formula (I) to pretilachlor is about 1:32 to about 1:2. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and pretilachlor, wherein the weight ratio of the benzyl ester of the compound of formula (I) to pretilachlor is about 1:32 to about 1:4. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and pretilachlor, wherein the weight ratio of the benzyl ester of the compound of formula (I) to pretilachlor is about 1:91 to about 2>7:1. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 40 grams active ingredient per hectare (gai/ha) to about 1050 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 43 grams active ingredient per hectare (gai/ha) to about 500 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and pretilachlor, e.g., sequentially or simultaneously. In some embodiments, the pretilachlor is applied at a rate from about 38 gai/ha to about 750 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the pretilachlor is applied at a rate from about 18 gai/ha to about 300 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 g acid equivalent per hectare (gae/ha) to about 45 gae/ha. In some embodiments, the pretilachlor is applied at a rate from about 37.5 gai/ha to about 150 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha. In some embodiments, the pretilachlor is applied at a rate from about 37.5 gai/ha to about 400 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 4.38 g acid equivalent per hectare (gae/ha) to about 100 gae/ha. In certain embodiments, the methods utilize the compound of formula (I), or its benzyl ester and pretilachlor. In one embodiment, the methods utilize the compound of formula (I) and pretilachlor, wherein the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha, and pretilachlor is applied at a rate of about 37.5 gai/ha to about 150 gai/ha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and pretilachlor, wherein the benzyl ester of the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 100 gae/ha, and pretilachlor is applied at a rate of about 37.5 gai/ha to about 400 gai/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with pretilachlor are used to control BRAPP, ECHCO, DIGSA, CYPIR, ECHCG, ECHOR, CYPRO, FIMMI, or SCPJU.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with prosulfocarb. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to prosulfocarb is within the range of from about 1:2000 to about 1:1.5. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to prosulfocarb is within the range of from about 1:1818 to about 1:10. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to prosulfocarb is within the range of from about 1:1600 to about 1:100. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and prosulfocarb. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 502 grams active ingredient per hectare (gai/ha) to about 4300 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 510 grams acid active ingredient per hectare (gai/ha) to about 4050 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 1,002 grams acid active ingredient per hectare (gai/ha) to about 4010 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and prosulfocarb, e.g., sequentially or simultaneously. In some embodiments, the prosulfocarb is applied at a rate from about 500 gai/ha to about 4000 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the prosulfocarb is applied at a rate from about 1,000 gai/ha to about 4,000 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2.0 gae/ha to about 100 gae/ha. In some embodiments, the prosulfocarb is applied at a rate from about 1,000 gai/ha to about 4,000 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2.5 gae/ha to about 10 gae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and prosulfocarb. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with prosulfocarb are used to control CHEAL, GALAP, KCHSC, PAPRH, SASKR, SINAR and STEME.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with pyroxasulfone. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to pyroxasulfone is within the range of from about 1:200 to about 12:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to pyroxasulfone is within the range of from about 1:15 to about 1:1. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and pyroxasulfone. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 27 grams active ingredient per hectare (gai/ha) to about 600 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 37 grams acid active ingredient per hectare (gai/ha) to about 150 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and pyroxasulfone, e.g., sequentially or simultaneously. In some embodiments, the pyroxasulfone is applied at a rate from about 500 gai/ha to about 4000 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the pyroxasulfone is applied at a rate from about 30 gai/ha to about 120 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 8 gae/ha to about 32 gae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and pyroxasulfone. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with pyroxasulfone are used to control ECHCG or BRAPP.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with thenylchlor. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to thenylchlor is within the range of from about 1:375 to about 4:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to thenylchlor is within the range of from about 1:341 to about 1:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to thenylchlor is within the range of from about 1:34 to about 1:1. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and thenylchlor. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 77 grams active ingredient per hectare (gai/ha) to about 1050 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 79 grams acid active ingredient per hectare (gai/ha) to about 800 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 143 grams acid active ingredient per hectare (gai/ha) to about 302 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and thenylchlor, e.g., sequentially or simultaneously. In some embodiments, the thenylchlor is applied at a rate from about 75 gai/ha to about 750 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the thenylchlor is applied at a rate from about 135 gai/ha to about 270 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 8 gae/ha to about 32 gae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and thenylchlor. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with thenychloror salt or ester thereof are used to control ECHOR and LEFCH.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with thiobencarb. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to thiobencarb is within the range of from about 1:2250 to about 1:4. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to thiobencarb is within the range of from about 1:511 to about 1:32. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to thiobencarb is within the range of from about 1:510 to about 1:17 In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to thiobencarb is within the range of from about 1:1000 to about 1:16. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to thiobencarb is within the range of from about 1:511 to about 1:32. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl ester and thiobencarb. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and thiobencarb, wherein the weight ratio of the benzyl ester of the compound of formula (I) to thiobencarb is about 1:511 to about 1:17. In one embodiment, the composition comprises the compound of formula (I) and thiobencarb, wherein the weight ratio of the compound of formula (I) to thiobencarb is about 1:511 to about 1:32. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and thiobencarb, wherein the weight ratio of the benzyl ester of the compound of formula (I) to thiobencarb is about 1:511 to about 1:64. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 562 grams active ingredient per hectare (gai/ha) to about 4,800 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 564 grams active ingredient per hectare (gai/ha) to about 2275 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and thiobencarb, e.g., sequentially or simultaneously. In some embodiments, the thiobencarb is applied at a rate from about 560 gai/ha to about 4500 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the thiobencarb is applied at a rate from about 280 gai/ha to about 5000 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 g acid equivalent per hectare (gae/ha) to about 45 gae/ha. In some embodiments, the thiobencarb is applied at a rate from about 560 gai/ha to about 2240 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha. In certain embodiments, the methods utilize the compound of formula (I), or its benzyl ester and thiobencarb. In one embodiment, the methods utilize the compound of formula (I) and thiobencarb, wherein the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha, and thiobencarb is applied at a rate of about 560 gai/ha to about 2240 gai/ha. In one embodiment, the methods utilize the compound of formula (I) and thiobencarb, wherein the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 35 gae/ha, and thiobencarb is applied at a rate of about 560 gai/ha to about 2240 gai/ha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and thiobencarb, wherein the benzyl ester of the compound of formula (I) is applied at a rate of from about 4.83 g acid equivalent per hectare (gae/ha) to about 35 gae/ha, and thiobencarb is applied at a rate of about 560 gai/ha to about 2240 gai/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with thiobencarb or salt or ester thereof are used to control ECHOR, CYPRO, DIGSA, CYPIR, ISCRU or ECHCO.
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 vegetation. When used in conjunction with other herbicides, the composition can be formulated with the other herbicide or herbicides, tank mixed with the other herbicide or herbicides or applied sequentially with the other herbicide or herbicides. Some of the herbicides that can be employed in conjunction with the compositions and methods described herein include, but are not limited to: 4-CPA; 4-CPB; 4-CPP; 2,4-D; 2,4-D choline salt, 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; acifluorfen, aclonifen, acrolein, alachlor, allidochlor, alloxydim, allyl alcohol, alorac, ametridione, ametryn, amibuzin, amicarbazone, amidosulfuron, aminocyclopyrachlor, aminopyralid, amiprofos-methyl, amitrole, ammonium sulfamate, anisuron, asulam, atraton, atrazine, azafenidin, azimsulfuron, aziprotryne, barban, BCPC, beflubutamid, benazolin, bencarbazone, benfluralin, bensulfuron-methyl, bensulide, benthiocarb, bentazon-sodium, benzadox, benzfendizone, benzipram, benzobicyclon, benzofenap, benzofluor, benzoylprop, benzthiazuron, bialaphos, bicyclopyrone, bifenox, bilanafos, bispyribac-sodium, borax, bromacil, bromobonil, bromobutide, bromofenoxim, bromoxynil, brompyrazon, butafenacil, butamifos, butenachlor, buthidazole, buthiuron, butralin, butroxydim, buturon, butylate, cacodylic acid, 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, chlornitrofen, 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, dimexano, dimidazon, dinitramine, dinofenate, dinoprop, dinosam, dinoseb, dinoterb, diphenamid, dipropetryn, diquat, disul, dithiopyr, diuron, DMPA, DNOC, DSMA, EBEP, eglinazine, endothal, epronaz, EPTC, erbon, 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, fenuron, ferrous sulfate, flamprop, flamprop-M, flazasulfuron, florasulam, fluazifop, fluazifop-P-butyl, fluazolate, flucarbazone, flucetosulfuron, fluchloralin, flufenican, flufenpyr-ethyl, flumetsulam, flumezin, flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, fluoromidine, fluoronitrofen, fluothiuron, flupoxam, flupropacil, flupropanate, flupyrsulfuron, fluridone, fluorochloridone, fluoroxypyr, fluoroxypyr-meptyl, flurtamone, fluthiacet, fomesafen, foramsulfuron, fosamine, fumiclorac, furyloxyfen, glufosinate, glufosinate-ammonium, glufosinate-P-ammonium, glyphosate salts and esters, halauxifen, halauxifen-methyl, halosafen, halosulfuron-methyl, haloxydine, haloxyfop-methyl, haloxyfop-P-methyl, hexachloroacetone, hexaflurate, hexazinone, imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazosulfuron, imazethapyr, 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, MAMA, MCPA esters and amines, MCPA-thioethyl, MCPB, mecoprop, mecoprop-P, medinoterb, 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, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, monalide, monisouron, monochloroacetic acid, monolinuron, monuron, morfamquat, MSMA, naproanilide, napropamide, naptalam, neburon, nicosulfuron, nipyraclofen, nitralin, nitrofen, nitrofluorfen, norflurazon, noruron, OCH, orbencarb, ortho-dichlorobenzene, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxapyrazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraflufen-ethyl, parafluoron, paraquat, pebulate, pelargonic acid, pendimethalin, penoxsulam, pentachlorophenol, pentanochlor, pentoxazone, perfluidone, phenisopham, phenmedipham, phenmedipham-ethyl, phenobenzuron, phenylmercury acetate, picloram, picolinafen, pinoxaden, piperophos, potassium arsenite, potassium azide, potassium cyanate, primisulfuron-methyl, procyazine, prodiamine, profluazol, profluralin, profoxydim, proglinazine, prohexadione-calcium, prometon, prometryn, pronamide, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propyrisulfuron, propyzamide, prosulfalin, prosulfuron, proxan, prynachlor, pydanon, pyraclonil, pyraflufen-ethyl, pyrasulfotole, pyrazogyl, pyrazolynate, pyrazosulfuron-ethyl, pyrazoxyfen, pyribenzoxim, pyributicarb, pyriclor, pyridafol, pyridate, pyriftalid, pyriminobac, pyrimisulfan, pyrithiobac-sodium, pyroxsulam, quinclorac, quinmerac, quinoclamine, quinonamid, quizalofop, quizalofop-P-ethyl, rhodethanil, rimsulfuron, saflufenacil, S-metolachlor, 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, tetrafluoron, thiazafluoron, thiazopyr, thidiazimin, thidiazuron, thiencarbazone-methyl, thifensulfuron, thifensulfurn-methyl, tiocarbazil, tioclorim, topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, tricamba, triclopyr choline salt, triclopyr esters and salts, tridiphane, trietazine, trifloxysulfuron, trifluralin, triflusulfuron, trifop, trifopsime, trihydroxytriazine, trimeturon, tripropindan, tritac tritosulfuron, vernolate, 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, aryloxyphenoxypropionate-tolerant, cyclohexanedione-tolerant, phenylpyrazoline-tolerant, ACCase-tolerant, imidazolinone-tolerant, sulfonylurea-tolerant, pyrimidinylthiobenzoate-tolerant, triazolopyrimidine-tolerant, sulfonylaminocarbonyltriazolinone-tolerant, ALS- or AHAS-tolerant, HPPD-tolerant, phytoene desaturase inhibitor-tolerant, carotenoid biosynthesis inhibitor tolerant, 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, bromoxynil-tolerant, and crops possessing multiple or stacked traits conferring tolerance to multiple chemistries and/or multiple modes of action via single and/or multiple resistance mechanisms. In some embodiments, the compound of formula (I) or salt or ester thereof and complementary herbicide or salt or ester thereof are used in combination with herbicides that are selective for the crop being treated and which complement 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 N-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 salt thereof. In certain embodiments, cloquintocet is utilized to antagonize harmful effects of the compositions on rice and cereals. In some embodiments, the safener is cloquintocet (mexyl).
In some embodiments, the compositions described herein are employed in combination with one or more plant growth regulators, such as 2,3,5-tri-iodobenzoic acid, IAA, IBA, naphthaleneacetamide, α-naphthaleneacetic acids, benzyladenine, 4-hydroxyphenethyl alcohol, kinetin, zeatin, endothal, ethephon, pentachlorophenol, thidiazuron, tribufos, aviglycine, maleic hydrazide, gibberellins, gibberellic acid, abscisic acid, ancymidol, fosamine, glyphosine, isopyrimol, jasmonic acid, maleic hydrazide, mepiquat, 2,3,5-tri-iodobenzoic acid, morphactins, dichlorflurenol, flurprimidol, mefluidide, paclobutrazol, tetcyclacis, uniconazole, brassinolide, brassinolide-ethyl, cycloheximide, ethylene, methasulfocarb, prohexadione, triapenthenol and trinexapac.
In some embodiments, the plant growth regulators are employed in one or more crops or settings, such as rice, cereal crops, corn, maize, broadleaf crops, oilseed rape/canola, turf, pineapple, sugarcane, sunflower, pastures, grasslands, rangelands, fallowland, turf, tree and vine orchards, plantation crops, vegetables, and non-crop (ornamentals) 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 VLCFA inhibitors or fatty acid/lipid synthesis inhibitors 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 selective weed control in the presence of crops, and should not react chemically with herbicidal components or other composition ingredients. Such mixtures can be designed for application directly to weeds or their locus or can be concentrates 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 concentrates, solutions, emulsions 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 quaternary ammonium salt; blend of petroleum hydrocarbon, alkyl esters, organic acid, and anionic surfactant; C9-C11 alkylpolyglycoside; phosphated alcohol ethoxylate; natural primary alcohol (C12-C16) 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 mineral 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, corn oil, cottonseed oil, linseed oil, palm oil, peanut oil, safflower 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 stearate, n-butyl oleate, isopropyl myristate, propylene glycol dioleate, di-octyl succinate, di-butyl adipate, di-octyl phthalate and the like; esters of mono, di and polycarboxylic acids and the like. Specific 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, glycerine, N-methyl-2-pyrrolidinone, N,N-dimethyl alkylamides, dimethyl sulfoxide, liquid fertilizers and the like. In certain embodiments, Water is the carrier for the dilution of concentrates.
Suitable solid carriers include but are not limited to talc, pyrophyllite clay, silica, attapulgus clay, kaolin clay, kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, Fuller's earth, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, lignin, cellulose, and the like.
In some embodiments, the compositions described herein further comprise one or more surface-active agents. In some embodiments, such surface-active agents are employed in both solid and liquid compositions, and in certain embodiments those designed to be diluted with carrier before application. The surface-active agents can be anionic, cationic or nonionic in character and can be employed as emulsifying agents, wetting agents, suspending agents, or for other purposes. Surfactants which may also be used in the present formulations are described, inter alia, in “McCutcheon's Detergents and Emulsifiers Annual,” MC Publishing Corp., Ridgewood, N.J., 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 addition products, such as nonylphenol-C18 ethoxylate; alcohol-alkylene oxide addition products, such as tridecyl alcohol-C16 ethoxylate; soaps, such as sodium stearate; alkyl-naphthalene-sulfonate salts, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl) sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryl trimethylammonium chloride; polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; 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, penetration 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 regulants, fungicides, 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 ingredients in the compositions described herein is from about 0.0005 to 98 percent by weight. In some embodiments, the concentration is from about 0.0006 to 90 percent by weight. In compositions designed to be employed as concentrates, the active ingredients, in certain embodiments, are present in a concentration from about 0.1 to 98 weight percent, and in certain embodiment's about 0.5 to 90 weight percent. Such compositions are, in certain embodiments, diluted with an inert carrier, such as water, before application. The diluted compositions usually applied to weeds or the locus of weeds contain, in certain embodiments, about 0.0006 to 10.0 weight percent active ingredient and in certain embodiments contain about 0.01 to 7.0 weight percent.
The present compositions can be applied to weeds or their locus by the use of conventional ground or aerial dusters, sprayers, and granule applicators, by addition to irrigation or paddy water, and by other conventional means known to those skilled in the art.
The described embodiments and following examples are for illustrative purposes and are not intended to limit the scope of the claims. Other modifications, uses, or combinations with respect to the compositions described herein will be apparent to a person of ordinary skill in the art without departing from the spirit and scope of the claimed subject matter.
EXAMPLES
Results in Examples I, II, III, and IV 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. Supplemental lighting was provided with overhead metal 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-2-fluoro-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 equivalent basis.
Forms of compound A (compound of formula I) tested include:




Other herbicidal components were applied on an active ingredient basis and included very long chain fatty acid (VLCFA) synthesis-inhibiting and fatty acid/lipid synthesis-inhibiting herbicides acetochlor (technical grade material), acetochlor+dichlormid formulated as Topnotch®, pretilachlor (technical grade material), butachlor formulated as Butachlor EC, fentrazamide formulated as Fentrazamide EC, thiobencarb formulated as Bolero® 8EC, cafenstrole formulated as Himeadow® WP or Lapost® Flowable, benfuresate formulated as Full Shot®, dimethenamid-P formulated as Outlook®, indanofan (technical grade material), flufenacet formulated as Define® DF, mefenacet (technical grade material), S-metolachlor formulated as Dual® II Magnum, pethoxamid formulated as Successor® 600, and pyroxasulfone (technical grade material).
Treatment requirements were calculated based upon the rates being tested, the concentration of active ingredient or acid equivalent 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 12× stock solutions. If a test compound did not dissolve readily, the mixture was warmed and/or sonicated. Application solutions were prepared by adding an appropriate amount of each stock solution (e.g., 1 mL) and diluted to the appropriate final concentrations with the addition of 10 mL of an aqueous mixture of 1.25% (v/v) crop oil concentrate so that the final spray solutions contained 1.25+/−0.05% (v/v) crop oil concentrate.
For treatments comprised of technical compounds, weighed amounts can be placed individually in 25 mL glass vials and dissolved in a volume of 97:3 v/v acetone/DMSO to obtain 12× 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 12× 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 12× 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.
All stock solutions and applications solutions were visually inspected for compound compatibility prior to application. Spray solutions were applied to the plant material with an overhead Mandel track sprayer equipped with a 8002E nozzles calibrated to deliver 187 L/ha over an application area of 0.503 m2 at a spray height of 18 to 20 inches (46 to 50 cm) above average plant canopy height. Control plants were sprayed in the same manner with the solvent blank.
The treated plants and control plants were placed in a greenhouse as described above and watered by sub-irrigation to prevent wash-off of the test compounds. After approximately 3 weeks, the condition of the test plants as compared with that of the untreated plants was determined visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury or growth inhibition and 100 corresponds to complete kill.
Colby's equation was used to determine 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 equation was used to calculate the expected activity of mixtures containing two active ingredients, A and B:

Expected=A+B−(A×B/100)

A=observed efficacy of active ingredient A at the same concentration as used in the mixture.
B=observed efficacy of active ingredient 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 1-25.







TABLE 1





Synergistic Activity of Foliar-Applied Compound A


Acid and Acetochlor Herbicidal Compositions on Control


of Weeds Common to Rice Cropping Systems.






















Visual Weed Control




Compound A

(%) - 20 DAA



Acid
Acetochlor
BRAPP












gae/ha
gai/ha
Obs
Exp







4.38
0
50
—



8.75
0
70
—



0
100
20
—



0
200
30
—



4.38
100
65
60



8.75
100
90
76



4.38
200
85
65



8.75
200
95
79

















Visual Weed Control



Compound A

(%) - 20 DAA



Acid
Acetochlor
DIGSA












gae/ha
gai/ha
Obs
Exp







4.38
0
30
—



17.5
0
40
—



0
100
20
—



0
200
20
—



4.38
100
50
44



17.5
100
75
52



4.38
200
60
44



17.5
200
80
52

















TABLE 2





Synergistic Activity of Foliar-Applied Compound A Benzyl


Ester and Acetochlor Herbicidal Compositions on Control


of Weeds Common to Rice Cropping Systems.






















Visual Weed Control




Compound A

(%) - 20 DAA



Benzyl Ester
Acetochlor
DIGSA












gae/ha
gai/ha
Obs
Exp







4.38
0
50
—



8.75
0
60
—



0
200
20
—



4.38
200
75
60



8.75
200
95
68

















Visual Weed Control



Compound A

(%) - 20 DAA



Benzyl Ester
Acetochlor
ECHCG












gae/ha
gai/ha
Obs
Exp







4.38
0
70
—



8.75
0
70
—



0
50
0
—



0
100
10
—



4.38
50
85
70



8.75
50
90
70



4.38
100
90
73



8.75
100
90
73

















TABLE 3





Synergistic Activity of Foliar-Applied Compound A Acid


and Acetochlor + Dichlormid Herbicidal Compositions


on Control of Weeds Common to Rice Cropping Systems.






















Visual Weed Control




Compound A
Acetochlor +
(%) - 20 DAA



Acid
dichlormid
ECHCG












gae/ha
gai/ha*
Obs
Exp







4.38
0
60
—



0
50
0
—



0
100
40
—



0
200
80
—



4.38
50
80
60



4.38
100
95
76



4.38
200
95
92

















Visual Weed Control



Compound A
Acetochlor +
(%) - 20 DAA



Acid
dichlormid
LEFCH












gae/ha
gai/ha*
Obs
Exp







4.38
0
0
—



8.75
0
30
—



17.5
0
30
—



0
50
0
—



0
100
0
—



0
200
40
—



4.38
50
60
 0



8.75
50
65
30



17.5
50
60
30



4.38
100
55
 0



8.75
100
55
30



17.5
100
70
30



4.38
200
60
40



8.75
200
70
58



17.5
200
65
58







*gai/ha refers to active ingredient of acetachlor.













TABLE 4





Synergistic Activity of Foliar-Applied Compound A Benzyl


Ester and Acetochlor + Dichlormid Herbicidal Compositions


on Control of Weeds Common to Rice Cropping Systems.






















Visual Weed Control




Compound A
Acetochlor +
(%) - 20 DAA



Benzyl Ester
dichlormid
DIGSA












gae/ha
gai/ha*
Obs
Exp







4.38
0
40
—



8.75
0
40
—



0
200
40
—



4.38
200
85
64



8.75
200
75
64

















Visual Weed Control



Compound A
Acetochlor +
(%) - 20 DAA



Benzyl Ester
dichlormid
LEFCH












gae/ha
gai/ha*
Obs
Exp







4.38
0
15
—



8.75
0
30
—



17.5
0
50
—



0
50
0
—



0
100
0
—



0
200
40
—



4.38
50
50
15



8.75
50
60
30



17.5
50
70
50



4.38
100
30
15



8.75
100
45
30



17.5
100
50
50



4.38
200
65
49



8.75
200
70
58



17.5
200
75
70







*gai/ha refers to active ingredient of acetachlor.













TABLE 5





Synergistic Activity of Foliar-Applied Compound


A Acid and Pretilachlor Herbicidal Compositions


on Weed Control in a Rice Cropping System.



















Visual Weed Control


Compound A

(%) - 20 DAA










Acid
Pretilachlor
BRAPP
ECHCO












gae/ha
gai/ha
Obs
Exp
Obs
Exp





4.38
0
50
—
65
—


8.75
0
70
—
85
—


0
37.5
0
—
0
—


0
75
0
—
0
—


0
150
0
—
0
—


4.38
37.5
65
50
95
65


8.75
37.5
80
70
90
85


4.38
75
65
50
85
65


8.75
75
70
70
95
85


4.38
150
70
50
95
65


8.75
150
90
70
90
85
















Visual Weed Control



Compound A

(%) - 20 DAA



Acid
Pretilachlor
DIGSA












gae/ha
gai/ha
Obs
Exp







4.38
0
30
—



17.5
0
40
—



0
37.5
0
—



0
75
0
—



0
150
0
—



4.38
37.5
50
30



17.5
37.5
50
40



4.38
75
40
30



17.5
75
85
40



4.38
150
50
30



17.5
150
75
40

















Visual Weed Control



Compound A

(%) - 20 DAA



Acid
Pretilachlor
CYPIR












gae/ha
gai/ha
Obs
Exp







4.38
0
40
—



0
37.5
0
—



0
75
0
—



0
150
0
—



4.38
37.5
100
40



4.38
75
99
40



4.38
150
100
40

















TABLE 6





Synergistic Activity of Foliar-Applied Compound A


Benzyl Ester and Pretilachlor Herbicidal Compositions


on Weed Control in a Rice Cropping System.






















Visual Weed Control




Compound A

(%) - 20 DAA



Benzyl Ester
Pretilachlor
DIGSA












gae/ha
gai/ha
Obs
Exp







4.38
0
50
—



8.75
0
60
—



0
75
0
—



0
150
0
—



4.38
75
80
50



8.75
75
75
60



4.38
150
50
50



8.75
150
75
60















Visual Weed Control


Compound A

(%) - 20 DAA










Benzyl Ester
Pretilachlor
ECHCO
ECHCG












gae/ha
gai/ha
Obs
Exp
Obs
Exp





4.38
0
60
—
70
—


8.75
0
85
—
70
—


0
37.5
0
—
10
—


0
75
0
—
10
—


0
150
0
—
0
—


4.38
37.5
80
60
80
73


8.75
37.5
95
85
95
73


4.38
75
80
60
85
73


8.75
75
95
85
99
73


4.38
150
90
60
80
70


8.75
150
90
85
85
70
















Visual Weed Control



Compound A

(%) - 20 DAA



Benzyl Ester
Pretilachlor
CYPIR












gae/ha
gai/ha
Obs
Exp







4.38
0
80
—



0
37.5
0
—



0
75
0
—



4.38
37.5
95
80



4.38
75
100
80

















TABLE 7





Synergistic Activity of Foliar-Applied Compound


A Acid and Butachlor Herbicidal Compositions


on Weed Control in a Rice Cropping System.




















Visual Weed Control



Compound A

(%) - 20 DAA












Acid
Butachlor
BRAPP

ECHCG













gae/ha
gai/ha
Obs
Exp
Obs
Exp





4.38
0
60
—
50
—


0
112.5
0
—
0
—


0
225
0
—
0
—


0
450
0
—
0
—


4.38
112.5
75
60
90
50


4.38
225
65
60
85
50


4.38
450
80
60
85
50
















Visual Weed Control



Compound A

(%) - 20 DAA



Acid
Butachlor
ECHCO












gae/ha
gai/ha
Obs
Exp







4.38
0
40
—



8.75
0
60
—



0
112.5
0
—



0
225
0
—



0
450
0
—



4.38
112.5
75
40



8.75
112.5
85
60



4.38
225
80
40



8.75
225
90
60



4.38
450
85
40



8.75
450
95
60

















Visual Weed Control



Compound A

(%) - 20 DAA



Acid
Butachlor
LEFCH












gae/ha
gai/ha
Obs
Exp







4.38
0
0
—



8.75
0
10
—



17.5
0
30
—



0
112.5
0
—



0
225
0
—



0
450
0
—



4.38
112.5
10
 0



8.75
112.5
20
10



17.5
112.5
65
30



4.38
225
NT
 0



8.75
225
30
10



17.5
225
60
30



4.38
450
75
 0



8.75
450
50
10



17.5
450
85
30

















Visual Weed Control



Compound A

(%) - 20 DAA



Acid
Butachlor
IPOHE












gae/ha
gai/ha
Obs
Exp







4.38
0
0
—



8.75
0
20
—



0
112.5
20
—



0
450
30
—



4.38
112.5
20
20



8.75
112.5
50
36



4.38
450
80
30



8.75
450
50
44

















TABLE 8





Synergistic Activity of Foliar-Applied Compound


A Benzyl and Butachlor Herbicidal Compositions


on Weed Control in a Rice Cropping System.




















Visual Weed Control



Compound A

(%) - 20 DAA












Benzyl Ester
Butachlor
BRAPP

ECHCO













gae/ha
gai/ha
Obs
Exp
Obs
Exp





4.38
0
60
—
60
—


8.75
0
65
—
70
—


0
112.5
0
—
0
—


0
225
0
—
0
—


0
450
0
—
0
—


4.38
112.5
80
60
70
60


8.75
112.5
85
65
85
70


4.38
225
65
60
80
60


8.75
225
80
65
85
70


4.38
450
70
60
80
60


8.75
450
95
65
80
70
















Visual Weed Control



Compound A

(%) - 20 DAA



Benzyl Ester
Butachlor
LEFCH












gae/ha
gai/ha
Obs
Exp







4.38
0
0
—



8.75
0
10
—



17.5
0
25
—



0
112.5
0
—



0
225
0
—



0
450
0
—



4.38
112.5
20
 0



8.75
112.5
45
10



17.5
112.5
40
25



4.38
225
20
 0



8.75
225
30
10



17.5
225
40
25



4.38
450
30
 0



8.75
450
30
10



17.5
450
45
25

















Visual Weed Control



Compound A

(%) - 20 DAA



Benzyl Ester
Butachlor
IPOHE












gae/ha
gai/ha
Obs
Exp







4.38
0
10
—



8.75
0
15
—



17.5
0
25
—



0
112.5
20
—



0
450
30
—



4.38
112.5
60
28



8.75
112.5
25
32



17.5
112.5
80
40



4.38
450
70
37



8.75
450
70
41



17.5
450
25
48

















TABLE 9





Synergistic Activity of Foliar-Applied Compound


A Acid and Fentrazamide Herbicidal Compositions


on Weed Control in a Rice Cropping System.






















Visual Weed Control




Compound A

(%) - 20 DAA



Acid
Fentrazamide
BRAPP












gae/ha
gai/ha
Obs
Exp







4.38
0
75
—



8.75
0
80
—



0
16.88
0
—



0
33.75
0
—



0
67.5
55
—



4.38
16.88
90
75



8.75
16.88
90
80



4.38
33.75
90
75



8.75
33.75
95
80



4.38
67.5
95
89



8.75
67.5
99
91















Visual Weed Control


Compound A

(%) - 20 DAA










Acid
Fentrazamide
ECHCG
ECHCO












gae/ha
gai/ha
Obs
Exp
Obs
Exp





4.38
0
60
—
70
—


0
16.88
0
—
0
—


0
33.75
0
—
15
—


0
67.5
20
—
10
—


4.38
16.88
90
60
95
70


4.38
33.75
90
60
95
75


4.38
67.5
90
68
95
73
















Visual Weed Control



Compound A

(%) - 20 DAA



Acid
Fentrazamide
LEFCH












gae/ha
gai/ha
Obs
Exp







4.38
0
15
—



8.75
0
30
—



17.5
0
50
—



0
33.75
0
—



0
67.5
0
—



4.38
33.75
10
15



8.75
33.75
50
30



17.5
33.75
60
50



4.38
67.5
30
15



8.75
67.5
40
30



17.5
67.5
65
50

















TABLE 10





Synergistic Activity of Foliar-Applied Compound A


Benzyl Ester and Fentrazamide Herbicidal Compositions


on Weed Control in a Rice Cropping System.






















Visual Weed Control




Compound A

(%) - 20 DAA



Benzyl Ester
Fentrazamide
DIGSA












gae/ha
gai/ha
Obs
Exp







8.75
0
30
—



17.5
0
30
—



0
33.75
0
—



0
67.5
30
—



8.75
33.75
45
30



17.5
33.75
45
30



8.75
67.5
90
51



17.5
67.5
85
51

















Visual Weed Control



Compound A

(%) - 20 DAA



Benzyl Ester
Fentrazamide
ECHCG












gae/ha
gai/ha
Obs
Exp







16
0
78
—



32
0
83
—



0
75
0
—



0
150
5
—



0
300
13
—



16
75
95
78



32
75
95
83



16
150
90
79



32
150
95
83



16
300
95
80



32
300
95
85

















TABLE 11





Synergistic Activity of Foliar-Applied Compound


A Acid and Thiobencarb Herbicidal Compositions


on Weed Control in a Rice Cropping System.






















Visual Weed Control




Compound A

(%) - 20 DAA



Acid
Thiobencarb
DIGSA












gae/ha
gai/ha
Obs
Exp







4.38
0
30
—



17.5
0
40
—



0
560
20
—



4.38
560
60
44



17.5
560
70
52

















Visual Weed Control



Compound A

(%) - 20 DAA



Acid
Thiobencarb
CYPIR












gae/ha
gai/ha
Obs
Exp







4.38
0
40
—



0
560
0
—



0
1120
0
—



0
2240
0
—



4.38
560
70
40



4.38
1120
95
40



4.38
2240
95
40

















TABLE 12





Synergistic Activity of Foliar-Applied Compound


A Benzyl Ester and Thiobencarb Herbicidal Compositions


on Weed Control in a Rice Cropping System.






















Visual Weed Control




Compound A

(%) - 20 DAA



Benzyl Ester
Thiobencarb
ECHCO












gae/ha
gai/ha
Obs
Exp







4.38
0
60
—



8.75
0
85
—



0
560
45
—



0
1120
40
—



4.38
560
90
78



8.75
560
95
92



4.38
1120
90
76



8.75
1120
95
91

















Visual Weed Control



Compound A

(%) - 21 DAA



Benzyl Ester
Thiobencarb
ISCRU












gae/ha
gai/ha
Obs
Exp







8
0
20
—



16
0
0
—



0
1120
0
—



0
2240
0
—



8
1120
0
20



16
1120
85
 0



8
2240
100
20



16
2240
100
 0

















TABLE 13





Synergistic Activity of Foliar-Applied Compound A Acid


and Cafenstrole (Himeadow ® WP) Herbicidal


Compositions on Weed Control in a Rice Cropping System.






















Visual Weed Control




Compound A

(%) - 20 DAA



Acid
Cafenstrole
ECHCG












gae/ha
gai/ha
Obs
Exp







4.38
0
50
—



0
26.25
10
—



0
52.5
15
—



0
105
15
—



4.38
26.25
65
55



4.38
52.5
70
58



4.38
105
70
58

















Visual Weed Control



Compound A

(%) - 20 DAA



Acid
Cafenstrole
ECHCO












gae/ha
gai/ha
Obs
Exp







4.38
0
40
—



8.75
0
60
—



0
26.25
10
—



0
52.5
10
—



0
105
10
—



4.38
26.25
40
46



8.75
26.25
75
64



4.38
52.5
60
46



8.75
52.5
85
64



4.38
105
75
46



8.75
105
90
64

















Visual Weed Control



Compound A

(%) - 20 DAA



Acid
Cafenstrole
LEFCH












gae/ha
gai/ha
Obs
Exp







4.38
0
0
—



8.75
0
10
—



17.5
0
30
—



0
52.5
0
—



0
105
0
—



4.38
52.5
30
 0



8.75
52.5
20
10



17.5
52.5
45
30



4.38
105
45
 0



8.75
105
30
10



17.5
105
30
30

















Visual Weed Control



Compound A

(%) - 20 DAA



Acid
Cafenstrole
IPOHE












gae/ha
gai/ha
Obs
Exp







4.38
0
0
—



8.75
0
20
—



17.5
0
40
—



0
26.25
0
—



0
105
30
—



4.38
26.25
20
 0



8.75
26.25
30
20



17.5
26.25
70
40



4.38
105
20
30



8.75
105
60
44



17.5
105
65
58

















TABLE 14





Synergistic Activity of Foliar-Applied Compound A Acid


and Cafenstrole (Lapost ® Flowable) Herbicidal


Compositions on Weed Control in a Rice Cropping System.






















Visual Weed Control




Compound A

(%) - 21 DAA



Acid
Cafenstrole
CYPIR












gae/ha
gai/ha
Obs
Exp







4.38
0
70
—



0
26.25
0
—



0
52.5
0
—



0
105
0
—



4.38
26.25
80
70



4.38
52.5
90
70



4.38
105
95
70















Visual Weed Control


Compound A

(%) - 21 DAA










Acid
Cafenstrole
ECHCG
LEFCH












gae/ha
gai/ha
Obs
Exp
Obs
Exp





17.5
0
88
—
20
—


35
0
85
—
45
—


0
210
0
—
23
—


17.5
210
90
88
68
38


35
210
97
85
73
57
















TABLE 15





Synergistic Activity of Foliar-Applied Compound A Benzyl


Ester and Cafenstrole (Himeadow ® WP) Herbicidal


Compositions on Weed Control in a Rice Cropping System.






















Visual Weed Control




Compound A

(%) - 20 DAA



Benzyl Ester
Cafenstrole
BRAPP












gae/ha
gai/ha
Obs
Exp







4.38
0
60
—



8.75
0
65
—



0
26.25
0
—



0
52.5
0
—



0
105
0
—



4.38
26.25
65
60



8.75
26.25
85
65



4.38
52.5
70
60



8.75
52.5
85
65



4.38
105
75
60



8.75
105
75
65

















Visual Weed Control



Compound A

(%) - 20 DAA



Benzyl Ester
Cafenstrole
LEFCH












gae/ha
gai/ha
Obs
Exp







4.38
0
0
—



8.75
0
10
—



17.5
0
25
—



0
26.25
0
—



0
52.5
0
—



0
105
0
—



4.38
26.25
20
 0



8.75
26.25
30
10



17.5
26.25
35
25



4.38
52.5
25
 0



8.75
52.5
20
10



17.5
52.5
35
25



4.38
105
20
 0



8.75
105
25
10



17.5
105
50
25

















Visual Weed Control



Compound A

(%) - 20 DAA



Benzyl Ester
Cafenstrole
IPOHE












gae/ha
gai/ha
Obs
Exp







17.5
0
25
—



0
26.25
0
—



0
105
30
—



17.5
26.25
50
25



17.5
105
90
48

















TABLE 16





Synergistic Activity of Foliar-Applied Compound A Benzyl


Ester and Cafenstrole (Lapost ® Flowable) Herbicidal


Compositions on Weed Control in a Rice Cropping System.






















Visual Weed Control




Compound A

(%) - 21 DAA



Benzyl Ester
Cafenstrole
IPOHE












gae/ha
gai/ha
Obs
Exp







4.38
0
0
—



8.75
0
10
—



17.5
0
30
—



0
26.25
0
—



4.38
26.25
20
 0



8.75
26.25
40
10



17.5
26.25
45
30

















Visual Weed Control



Compound A

(%) - 21 DAA



Benzyl Ester
Cafenstrole
IPOHE












gae/ha
gai/ha
Obs
Exp







17.5
0
10
—



0
210
10
—



17.5
210
30
19

















Visual Weed Control



Compound A

(%) - 21 DAA



Benzyl Ester
Cafenstrole
SCPJU












gae/ha
gai/ha
Obs
Exp







4.38
0
40
—



0
26.25
0
—



0
52.5
0
—



0
105
0
—



4.38
26.25
100
40



4.38
52.5
100
40



4.38
105
100
40

















TABLE 17





Synergistic Activity of Foliar-Applied Compound


A Acid and Benfuresate Herbicidal Compositions


on Weed Control in a Rice Cropping System.



















Visual Weed Control


Compound A

(%) - 22 DAA










Acid
Benfuresate
ECHCG
ECHCO












gae/ha
gai/ha
Obs
Exp
Obs
Exp





5.3
0
65
—
65
—


10.6
0
55
—
65
—


0
75
0
—
0
—


0
150
0
—
0
—


0
300
0
—
0
—


5.3
75
65
65
80
65


10.6
75
80
55
80
65


5.3
150
75
65
85
65


10.6
150
90
55
85
65


5.3
300
90
65
85
65


10.6
300
90
55
90
65
















Visual Weed Control



Compound A

(%) - 22 DAA



Acid
Benfuresate
LEFCH












gae/ha
gai/ha
Obs
Exp







10.6
0
10
—



21.2
0
10
—



0
300
10
—



10.6
300
50
19



21.2
300
60
19

















Visual Weed Control



Compound A

(%) - 22 DAA



Acid
Benfuresate
CYPIR












gae/ha
gai/ha
Obs
Exp







5.3
0
60
—



0
150
0
—



0
300
10
—



5.3
150
99
60



5.3
300
100
64

















TABLE 18





Synergistic Activity of Foliar-Applied Compound


A Benzyl Ester and Benfuresate Herbicidal Compositions


on Weed Control in a Rice Cropping System.



















Visual Weed Control


Compound A

(%) - 22 DAA










Benzyl Ester
Benfuresate
ECHCG
ECHCO












gae/ha
gai/ha
Obs
Exp
Obs
Exp





5.3
0
40
—
30
—


10.6
0
60
—
55
—


0
75
0
—
0
—


0
150
0
—
0
—


0
300
0
—
0
—


5.3
75
40
40
55
30


10.6
75
55
60
60
55


5.3
150
65
40
85
30


10.6
150
85
60
70
55


5.3
300
85
40
75
30


10.6
300
90
60
85
55
















Visual Weed Control



Compound A

(%) - 21 DAA



Benzyl Ester
Benfuresate
LEFCH












gae/ha
gai/ha
Obs
Exp







5.3
0
0
—



10.6
0
20
—



21.2
0
35
—



0
75
0
—



0
150
10
—



0
300
10
—



5.3
75
40
 0



10.6
75
40
20



21.2
75
75
35



5.3
150
20
10



10.6
150
60
28



21.2
150
80
42



5.3
300
70
10



10.6
300
40
28



21.2
300
70
42

















TABLE 19





Synergistic Activity of Foliar-Applied Compound A


Benzyl Ester and Dimethenamid-P Herbicidal Compositions


on Weed Control in a Rice Cropping System.






















Visual Weed Control




Compound A

(%) - 20 DAA



Benzyl Ester
Dimethenamid-P
ECHCO












gae/ha
gai/ha
Obs
Exp







8
0
40



16
0
60



32
0
90



0
275
70



8
275
95
82



16
275
95
88



32
275
95
97

















Visual Weed Control



Compound A

(%) - 20 DAA



Benzyl Ester
Dimethenamid-P
CYPES












gae/ha
gai/ha
Obs
Exp







8
0
0
—



16
0
75
—



0
275
0
—



8
275
100
 0



16
275
100
75

















TABLE 20







Synergistic Activity of Foliar-Applied Compound


A Benzyl Ester and Flufenacet Herbicidal Compositions


on Weed Control in a Rice Cropping System.














Visual Weed Control




Compound A

(%) - 22 DAA



Benzyl Ester
Flufenacet
BRAPP












gae/ha
gai/ha
Obs
Exp
















8
0
60
—



16
0
60
—



32
0
90
—



0
187.5
10
—



0
375
20
—



0
750
40
—



8
187.5
80
64



16
187.5
90
64



32
187.5
90
91



8
375
75
68



16
375
90
68



32
375
95
92



8
750
80
76



16
750
95
76



32
750
95
94

















TABLE 21





Synergistic Activity of Foliar-Applied Compound


A Benzyl Ester and Indanofan Herbicidal Compositions


on Weed Control in a Rice Cropping System.






















Visual Weed Control




Compound A

(%) - 19 DAA



Benzyl Ester
Indanofan
ECHCO












gae/ha
gai/ha
Obs
Exp







8
0
65
—



0
37.5
0
—



0
75
0
—



0
150
35
—



8
37.5
80
65



8
75
85
65



8
150
90
77

















Visual Weed Control



Compound A

(%) - 19 DAA



Benzyl Ester
Indanofan
LEFCH












gae/ha
gai/ha
Obs
Exp







16
0
45
—



32
0
50
—



0
37.5
0
—



0
75
0
—



16
37.5
60
45



32
37.5
50
50



16
75
65
45



32
75
60
50

















TABLE 22





Synergistic Activity of Foliar-Applied Compound


A Benzyl Ester and Mefenacet Herbicidal Compositions


on Weed Control in a Rice Cropping System.






















Visual Weed Control




Compound A

(%) - 22 DAA



Benzyl Ester
Mefenacet
BRAPP












gae/ha
gai/ha
Obs
Exp







8
0
65
—



16
0
80
—



32
0
85
—



0
50
0
—



0
100
0
—



0
200
0
—



8
50
80
65



16
50
90
80



32
50
85
85



8
100
75
65



16
100
90
80



32
100
99
85



8
200
80
65



16
200
90
80



32
200
90
85

















Visual Weed Control



Compound A

(%) - 22 DAA



Benzyl Ester
Mefenacet
LEFCH












gae/ha
gai/ha
Obs
Exp







8
0
35
—



16
0
40
—



0
50
10
—



0
100
0
—



8
50
20
42



16
50
60
46



8
100
55
35



16
100
40
40

















Visual Weed Control



Compound A

(%) - 22 DAA



Benzyl Ester
Mefenacet
CYPIR












gae/ha
gai/ha
Obs
Exp







16
0
60
—



0
100
0
—



0
200
20
—



16
100
100
60



16
200
100
68

















TABLE 23







Synergistic Activity of Foliar-Applied Compound A


Benzyl Ester and S-Metolachlor Herbicidal Compositions


on Weed Control in a Rice Cropping System.














Visual Weed Control




Compound A

(%) - 20 DAA



Benzyl Ester
S-metolachlor
ECHCG












gae/ha
gai/ha
Obs
Exp
















8
0
63
—



16
0
78
—



32
0
83
—



0
387.5
20
—



0
775
55
—



8
387.5
95
70



16
387.5
95
82



32
387.5
95
86



8
775
90
83



16
775
95
90



32
775
95
92

















TABLE 24





Synergistic Activity of Foliar-Applied Compound


A Benzyl Ester and Pethoxamid Herbicidal Compositions


on Weed Control in a Rice Cropping System.






















Visual Weed Control




Compound A

(%) - 21 DAA



Benzyl Ester
Pethoxamid
LEFCH












gae/ha
gai/ha
Obs
Exp







8
0
20
—



0
305
10
—



0
610
10
—



8
305
40
28



8
610
45
28















Visual Weed Control


Compound A

(%) - 21 DAA










Benzyl Ester
Pethoxamid
CYPES
CYPIR












gae/ha
gai/ha
Obs
Exp
Obs
Exp





8
0
85
—
30
—


0
305
0
—
40
—


0
610
25
—
80
—


0
1220
65
—
85
—


8
305
100
85
100
58


8
610
100
89
100
86


8
1220
95
95
100
90
















TABLE 25





Synergistic Activity of Foliar-Applied Compound A


Benzyl Ester and Pyroxasulfone Herbicidal Compositions


on Weed Control in a Rice Cropping System.






















Visual Weed Control




Compound A

(%) - 22 DAA



Benzyl Ester
Pyroxasulfone
BRAPP












gae/ha
gai/ha
Obs
Exp







8
0
60
—



16
0
60
—



32
0
90
—



0
29.5
0
—



0
59
0
—



0
118
20
—



8
29.5
75
60



16
29.5
50
60



32
29.5
90
90



8
59
75
60



16
59
85
60



32
59
99
90



8
118
80
68



16
118
95
68



32
118
99
92

















Visual Weed Control



Compound A

(%) - 22 DAA



Benzyl Ester
Pyroxasulfone
ECHCG












gae/ha
gai/ha
Obs
Exp







8
0
25
—



16
0
50
—



32
0
85
—



0
59
70
—



8
59
90
78



16
59
85
85



32
59
99
96













BRAPP
Urochloa platyphylla (Nash)
signalgrass, broadleaf



R. D. Webster or Brachiaria



platyphylla (Griseb.) Nash


CYPIR
Cyperus iria L.
flatsedge, rice


CYPES
Cyperus esculentus L.
nutsedge, yellow


DIGSA
Digitaria sanguinalis (L.) Scop.
crabgrass, large


ECHCG
Echinochloa crusgalli (L.) Beauv.
barnyardgrass


ECHCO
Echinochloa colona (L.) Link
junglerice


IPOHE
Ipomoea hederacea Jacq.
morningglory, ivyleaf


ISCRU
Ischaemum rugosum Salisb.
saramollagrass


LEFCH
Leptochloa chinensis (L.) Nees
sprangletop, Chinese


SCPJU
Schoenoplectus juncoides (Roxb.) Palla
bulrush, Japanese





gae/ha = grams acid equivalent per hectare


gai/ha = grams active ingredient per hectare


Obs = observed value


Exp = expected value as calculated by Colby's equation


DAA = days after application


NT = not tested






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 mineral 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 volumetric 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 overnight 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 840 mL of mud contained in 32-oz. non-perforated plastic pots with a surface area of 86.59 cm2 4 days prior to herbicide application. The paddy was created by filling the headspace of the pots with 2.5 to 3 cm of water. When required to ensure good germination and healthy plants, a fungicide treatment and/or other chemical or physical treatment was applied. The plants were grown for 4-22 days in a greenhouse with an approximate 14 hr photoperiod which was maintained at about 29′C during the day and 26° C. during the night. Nutrients were added as Osmocote® (19:6:12, N:P:K+ minor nutrients) at 2 g per 16-oz. pot and 4 g per 32-oz. pot. Water was added on a regular basis to maintain the paddy flood, and supplemental lighting was provided with overhead metal 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-2-fluoro-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 equivalent basis.
Forms of compound A (compound of formula I) tested include:




The herbicidal components were applied on an active ingredient basis and included very long chain fatty acid (VLCFA) synthesis-inhibiting and fatty acid/lipid synthesis-inhibiting herbicides acetochlor (technical grade material), acetochlor+dichlormid formulated as Topnotch®, pretilachlor (technical grade material), butachlor formulated as Butachlor EC, fentrazamide formulated as Fentrazamide EC, thiobencarb formulated as Bolero® 8EC, cafenstrole formulated as Himeadow® WP or Lapost® Flowable, benfuresate formulated as Full Shot®, anilofos (technical grade material), mefenacet (technical grade material), molinate (technical grade material), and thenylchlor (technical grade material).

Treatment requirements for each compound or herbicidal component were calculated based upon the rates being tested, the concentration of active ingredient or acid equivalent 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. If the test compound did not dissolve readily, the mixture was warmed and/or sonicated. The concentrated stock solutions obtained were diluted with an equivalent 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. Control plants were treated in the same manner with the solvent blank. Applications were made so that all treated plant material received the same concentrations of acetone and crop oil concentrate.
The treated plants and control plants were placed in a greenhouse as described above and water was added as needed to maintain a paddy flood. After approximately 3 weeks the condition of the test plants as compared with that of the untreated plants was determined visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury or growth inhibition and 100 corresponds to complete kill.
Colby's equation was used to determine 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 equation was used to calculate the expected activity of mixtures containing two active ingredients, A and B:

Expected=A+B−(A×B/100)

A=observed efficacy of active ingredient A at the same concentration as used in the mixture.
B=observed efficacy of active ingredient 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 26-48.







TABLE 26





Synergistic Activity of In-Water Applications of Compound


A Acid and Acetochlor Herbicidal Compositions on Control


of Weeds Common to Rice Cropping Systems.






















Visual Weed Control




Compound A

(%) - 20 DAA



Acid
Acetochlor
ECHOR












gae/ha
gai/ha
Obs
Exp







8.75
0
10
—



17.5
0
25
—



35
0
25
—



0
100
80
—



8.75
100
100
82



17.5
100
100
85



35
100
100
85

















Visual Weed Control



Compound A

(%) - 22 DAA



Acid
Acetochlor
ECHCG












gae/ha
gai/ha
Obs
Exp







8.75
0
0
—



17.5
0
15
—



35
0
15
—



0
100
65
—



8.75
100
99
65



17.5
100
100
70



35
100
100
70

















Visual Weed Control



Compound A

(%) - 20 DAA



Acid
Acetochlor
CYPRO












gae/ha
gai/ha
Obs
Exp







8.75
0
0
—



17.5
0
70
—



0
100
20
—



0
200
75
—



8.75
100
100
20



17.5
100
100
76



8.75
200
100
75



17.5
200
99
93

















TABLE 27





Synergistic Activity of In-Water Applications of Compound


A Benzyl Ester and Acetochlor Herbicidal Compositions on


Control of Weeds Common to Rice Cropping Systems.



















Visual Weed Control


Compound A

(%) - 20 DAA










Benzyl Ester
Acetochlor
ECHOR
CYPRO












gae/ha
gai/ha
Obs
Exp
Obs
Exp





4.38
0
10
—
0
—


8.75
0
20
—
20
—


17.5
0
50
—
95
—


0
100
80
—
20
—


4.38
100
100
82
95
20


8.75
100
100
84
99
36


17.5
100
100
90
100
96
















Visual Weed Control



Compound A

(%) - 22 DAA



Benzyl Ester
Acetochlor
ECHCG












gae/ha
gai/ha
Obs
Exp







4.38
0
10
—



8.75
0
25
—



17.5
0
60
—



0
100
65
—



4.38
100
100
69



8.75
100
100
74



17.5
100
100
86

















Visual Weed Control



Compound A

(%) - 20 DAA



Benzyl Ester
Acetochlor
FIMMI












gae/ha
gai/ha
Obs
Exp







4.38
0
30
—



8.75
0
60
—



0
100
80
—



0
200
20
—



4.38
100
100
86



8.75
100
100
92



4.38
200
100
44



8.75
200
100
68

















TABLE 28







Synergistic Activity of In-Water Applications of Compound


A Acid and Acetochlor + Dichlormid Herbicidal Compositions


on Control of Weeds Common to Rice Cropping Systems.














Visual Weed Control




Compound A
Acetochlor +
(%) - 20 DAA



Acid
dichlormid
CYPRO












gae/ha
gai/ha*
Obs
Exp
















8.75
0
0
—



17.5
0
20
—



35
0
80
—



0
100
0
—



0
200
70
—



8.75
100
90
 0



17.5
100
100
20



35
100
95
80



8.75
200
100
70



17.5
200
100
76



35
200
100
94







*gai/ha refers to active ingredient of acetachlor.













TABLE 29







Synergistic Activity of In-Water Applications of Compound A


Benzyl Ester and Acetochlor + Dichlormid Herbicidal Compositions


on Control of Weeds Common to Rice Cropping Systems.














Visual Weed Control




Compound A
Acetochlor +
(%) - 20 DAA



Benzyl Ester
dichlormid
CYPRO












gae/ha
gai/ha*
Obs
Exp
















4.38
0
70
—



8.75
0
30
—



0
100
0
—



0
200
70
—



4.38
100
99
70



8.75
100
100
30



4.38
200
100
91



8.75
200
100
79







*gai/ha refers to active ingredient of acetachlor.













TABLE 30





Synergistic Activity of In-Water Applications of


Compound A Acid and Pretilachlor Herbicidal Compositions


on Weed Control in a Rice Cropping System.



















Visual Weed Control


Compound A

(%) - 20 DAA










Acid
Pretilachlor
ECHOR
CYPRO












gae/ha
gai/ha
Obs
Exp
Obs
Exp





8.75
0
10
—
0
—


17.5
0
25
—
70
—


35
0
25
—
90
—


0
75
0
—
0
—


0
150
30
—
0
—


8.75
75
35
10
0
0


17.5
75
85
25
100
70


35
75
80
25
100
90


8.75
150
95
37
75
0


17.5
150
80
48
100
70


35
150
100
48
100
90














Visual Weed Control


Compound A

(%) - 20 DAA










Acid
Pretilachlor
FIMMI
SCPJU












gae/ha
gai/ha
Obs
Exp
Obs
Exp





8.75
0
50
—
40
—


0
75
40
—
50
—


0
150
45
—
20
—


8.75
75
100
70
90
70


8.75
150
100
73
95
52
















TABLE 31





Synergistic Activity of In-Water Applications of Compound


A Benzyl Ester and Pretilachlor Herbicidal Compositions


on Weed Control in a Rice Cropping System.






















Visual Weed Control




Compound A

(%) - 20 DAA



Benzyl Ester
Pretilachlor
ECHOR












gae/ha
gai/ha
Obs
Exp







4.38
0
10
—



8.75
0
20
—



17.5
0
50
—



0
75
0
—



0
150
30
—



4.38
75
85
10



8.75
75
75
20



17.5
75
95
50



4.38
150
85
37



8.75
150
95
44



17.5
150
99
65















Visual Weed Control


Compound A

(%) - 20 DAA










Benzyl Ester
Pretilachlor
CYPRO
FIMMI












gae/ha
gai/ha
Obs
Exp
Obs
Exp





4.38
0
0
—
30
—


8.75
0
20
—
60
—


0
75
0
—
40
—


0
150
0
—
45
—


4.38
75
0
0
100
58


8.75
75
85
20
100
76


4.38
150
40
0
100
62


8.75
150
75
20
100
78
















TABLE 32





Synergistic Activity of In-Water Applications of


Compound A Acid and Butachlor Herbicidal Compositions


on Weed Control in a Rice Cropping System.




















Visual Weed Control



Compound A

(%) - 21 DAA












Acid
Butachlor
ECHCG

ECHOR













gae/ha
gai/ha
Obs
Exp
Obs
Exp





8.75
0
0
—
30
—


17.5
0
0
—
25
—


35
0
20
—
30
—


0
225
40
—
0
—


0
450
20
—
20
—


8.75
225
20
40
85
30


17.5
225
40
40
95
25


35
225
95
52
95
30


8.75
450
50
20
70
44


17.5
450
60
20
99
40


35
450
95
36
99
44
















Visual Weed Control



Compound A

(%) - 21 DAA



Acid
Butachlor
CYPRO












gae/ha
gai/ha
Obs
Exp







8.75
0
0
—



0
225
0
—



0
450
0
—



8.75
225
70
0



8.75
450
15
0

















TABLE 33





Synergistic Activity of In-Water Applications of Compound


A Benzyl Ester and Butachlor Herbicidal Compositions


on Weed Control in a Rice Cropping System.




















Visual Weed Control



Compound A

(%) - 21 DAA












Benzyl Ester
Butachlor
ECHCG

ECHOR













gae/ha
gai/ha
Obs
Exp
Obs
Exp





4.38
0
15
—
0
—


8.75
0
20
—
15
—


17.5
0
75
—
10
—


0
225
40
—
0
—


0
450
20
—
20
—


4.38
225
45
49
75
 0


8.75
225
75
52
99
15


17.5
225
95
85
95
10


4.38
450
50
32
50
20


8.75
450
70
36
95
32


17.5
450
95
80
95
28
















Visual Weed Control



Compound A

(%) - 21 DAA



Benzyl Ester
Butachlor
CYPRO












gae/ha
gai/ha
Obs
Exp







4.38
0
0
—



8.75
0
30
—



0
225
0
—



0
450
0
—



4.38
225
30
0



8.75
225
85
30



4.38
450
80
0



8.75
450
60
30

















TABLE 34







Synergistic Activity of In-Water Applications of


Compound A Acid and Fentrazamide Herbicidal Compositions


on Weed Control in a Rice Cropping System.














Visual Weed Control




Compound A

(%) - 21 DAA



Acid
Fentrazamide
ECHOR












gae/ha
gai/ha
Obs
Exp
















8.75
0
10
—



17.5
0
20
—



35
0
35
—



0
50
50
—



8.75
50
90
55



17.5
50
80
60



35
50
95
68

















TABLE 35







Synergistic Activity of In-Water Applications of Compound


A Benzyl Ester and Fentrazamide Herbicidal Compositions


on Weed Control in a Rice Cropping System.














Visual Weed Control




Compound A

(%) - 21 DAA



Benzyl Ester
Fentrazamide
ECHOR












gae/ha
gai/ha
Obs
Exp
















4.38
0
25
—



8.75
0
25
—



17.5
0
60
—



0
50
50
—



4.38
50
70
63



8.75
50
85
63



17.5
50
95
80

















TABLE 36







Synergistic Activity of In-Water Applications of


Compound A Acid and Thiobencarb Herbicidal Compositions


on Weed Control in a Rice Cropping System.














Visual Weed Control




Compound A

(%) - 20 DAA



Acid
Thiobencarb
ECHOR












gae/ha
gai/ha
Obs
Exp
















8.75
0
10
—



17.5
0
25
—



35
0
25
—



0
1120
60
—



8.75
1120
85
64



17.5
1120
99
70



35
1120
99
70

















TABLE 37





Synergistic Activity of In-Water Applications of Compound


A Benzyl Ester and Thiobencarb Herbicidal Compositions


on Weed Control in a Rice Cropping System.






















Visual Weed Control




Compound A

(%) - 20 DAA



Benzyl Ester
Thiobencarb
ECHOR












gae/ha
gai/ha
Obs
Exp







4.38
0
10
—



8.75
0
20
—



17.5
0
50
—



0
1120
60
—



0
2240
90
—



4.38
1120
99
64



8.75
1120
95
68



17.5
1120
100
80



4.38
2240
99
91



8.75
2240
99
92



17.5
2240
100
95

















Visual Weed Control



Compound A

(%) - 20 DAA



Benzyl Ester
Thiobencarb
CYPRO












gae/ha
gai/ha
Obs
Exp







4.38
0
0
—



8.75
0
20
—



17.5
0
95
—



0
1120
0
—



0
2240
0
—



4.38
1120
0
0



8.75
1120
95
20



17.5
1120
95
95



4.38
2240
90
0



8.75
2240
85
20



17.5
2240
100
95

















TABLE 38







Synergistic Activity of In-Water Applications of Compound


A Acid and Cafenstrole (Himeadow ® WP) Herbicidal


Compositions on Weed Control in a Rice Cropping System.











Visual Weed Control


Compound A

(%) - 21 DAA










Acid
Cafenstrole
ECHCG
ECHOR












gae/ha
gai/ha
Obs
Exp
Obs
Exp















8.75
0
0
—
30
—


17.5
0
0
—
25
—


35
0
20
—
30
—


0
52.5
20
—
10
—


0
105
25
—
30
—


8.75
52.5
50
20
75
37


17.5
52.5
45
20
50
33


35
52.5
99
36
100
37


8.75
105
80
25
100
51


17.5
105
95
25
99
48


35
105
100
40
95
51
















TABLE 39





Synergistic Activity of In-Water Applications of Compound


A Benzyl Ester and Cafenstrole (Himeadow ® WP) Herbicidal


Compositions on Weed Control in a Rice Cropping System.



















Visual Weed Control


Compound A

(%) - 21 DAA










Benzyl Ester
Cafenstrole
ECHCG
ECHOR












gae/ha
gai/ha
Obs
Exp
Obs
Exp





4.38
0
15
—
0
—


8.75
0
20
—
15
—


17.5
0
75
—
10
—


0
52.5
20
—
10
—


0
105
25
—
30
—


4.38
52.5
95
32
50
10


8.75
52.5
95
36
100
24


17.5
52.5
100
80
100
19


4.38
105
60
36
85
30


8.75
105
99
40
100
41


17.5
105
100
81
99
37
















Visual Weed Control



Compound A

(%) - 21 DAA



Benzyl Ester
Cafenstrole
CYPRO












gae/ha
gai/ha
Obs
Exp







4.38
0
0
—



8.75
0
30
—



0
52.5
0
—



0
105
0
—



4.38
52.5
0
0



8.75
52.5
90
30



4.38
105
20
0



8.75
105
80
30

















TABLE 40





Synergistic Activity of In-Water Applications of Compound


A Acid and Cafenstrole (Lapost ® Flowable) Herbicidal


Compositions on Weed Control in a Rice Cropping System.






















Visual Weed Control




Compound A

(%) - 21 DAA



Acid
Cafenstrole
ECHOR












gae/ha
gai/ha
Obs
Exp







8.75
0
10
—



17.5
0
10
—



35
0
15
—



0
52.5
70
—



8.75
52.5
95
73



17.5
52.5
99
73



35
52.5
95
75

















Visual Weed Control



Compound A

(%) - 21 DAA



Acid
Cafenstrole
CYPRO












gae/ha
gai/ha
Obs
Exp







8.75
0
0
—



17.5
0
20
—



0
52.5
0
—



0
105
0
—



8.75
52.5
95
0



17.5
52.5
100
20



8.75
105
95
0



17.5
105
90
20

















Visual Weed Control



Compound A

(%) - 21 DAA



Acid
Cafenstrole
LEFCH












gae/ha
gai/ha
Obs
Exp







35
0
5
—



70
0
23
—



0
210
38
—



35
210
58
41



70
210
55
52

















TABLE 41





Synergistic Activity of In-Water Applications of Compound


A Benzyl Ester and Cafenstrole (Lapost ® Flowable)


Herbicidal Compositions on Weed Control in a Rice Cropping System.






















Visual Weed Control




Compound A

(%) - 21 DAA



Benzyl Ester
Cafenstrole
ECHOR












gae/ha
gai/ha
Obs
Exp







4.38
0
25
—



8.75
0
25
—



17.5
0
25
—



0
52.5
70
—



4.38
52.5
90
78



8.75
52.5
99
78



17.5
52.5
99
78

















Visual Weed Control



Compound A

(%) - 21 DAA



Benzyl
Cafenstrole
LEFCH












gae/ha
gai/ha
Obs
Exp







35
0
50
—



70
0
50
—



0
210
38
—



35
210
88
69



70
210
80
69

















TABLE 42





Synergistic Activity of In-Water Applications of Compound


A Acid and Benfuresate (Full Slot ®) Herbicidal


Compositions on Weed Control in a Rice Cropping System.






















Visual Weed Control




Compound A

(%) - 22 DAA



Acid
Benfuresate
ECHCG












gae/ha
gai/ha
Obs
Exp







42.4
0
30
—



0
75
0
—



0
150
0
—



42.4
75
50
30



42.4
150
95
30

















Visual Weed Control



Compound A

(%) - 22 DAA



Acid
Benfuresate
LEFCH












gae/ha
gai/ha
Obs
Exp







10.6
0
20
—



21.2
0
40
—



42.4
0
60
—



0
75
0
—



0
150
0
—



10.6
75
20
20



21.2
75
40
40



42.4
75
100
60



10.6
150
60
20



21.2
150
80
40



42.4
150
100
60

















TABLE 43





Synergistic Activity of In-Water Applications of Compound


A Benzyl Ester and Benfuresate (Full Slot) Herbicidal Compositions


on Weed Control in a Rice Cropping System.






















Visual Weed Control




Compound A

(%) - 22 DAA



Benzyl Ester
Benfuresate
ECHOR












gae/ha
gai/ha
Obs
Exp







8.75
0
35
—



17.5
0
30
—



0
75
0
—



0
150
0
—



8.75
75
15
35



17.5
75
95
30



8.75
150
80
35



17.5
150
95
30

















Visual Weed Control



Compound A

(%) - 22 DAA



Benzyl Ester
Benfuresate
LEFCH












gae/ha
gai/ha
Obs
Exp







4.38
0
20
—



0
75
0
—



0
150
0
—



4.38
75
45
20



4.38
150
100
20

















TABLE 44





Synergistic Activity of In-Water Applications of Compound


A Benzyl Ester and Anilofos Herbicidal Compositions


on Weed Control in a Rice Cropping System.






















Visual Weed Control




Compound A

(%) - 19 DAA



Benzyl Ester
Anilofos
ECHCG












gae/ha
gai/ha
Obs
Exp







8
0
30
—



16
0
20
—



32
0
40
—



0
100
20
—



8
100
20
44



16
100
95
36



32
100
99
52

















Visual Weed Control



Compound A

(%) - 19 DAA



Benzyl Ester
Anilofos
ECHOR












gae/ha
gai/ha
Obs
Exp







8
0
10
—



16
0
20
—



32
0
25
—



0
100
40
—



0
200
80
—



8
100
60
46



16
100
50
52



32
100
50
55



8
200
95
82



16
200
99
84



32
200
95
85

















Visual Weed Control



Compound A

(%) - 19 DAA



Benzyl Ester
Anilofos
CYPRO












gae/ha
gai/ha
Obs
Exp







8
0
50
—



0
100
0
—



0
200
0
—



0
400
0
—



8
100
85
50



8
200
100
50



8
400
80
50

















Visual Weed Control



Compound A

(%) - 19 DAA



Benzyl Ester
Anilofos
FIMMI












gae/ha
gai/ha
Obs
Exp







8
0
0
—



16
0
0
—



32
0
85
—



0
100
0
—



0
200
0
—



0
400
10
—



8
100
0
 0



16
100
20
 0



32
100
100
85



8
200
10
 0



16
200
40
 0



32
200
100
85



8
400
25
10



16
400
30
10



32
400
100
87

















TABLE 45







Synergistic Activity of In-Water Applications of Compound


A Benzyl Ester and Indanofan Herbicidal Compositions


on Weed Control in a Rice Cropping System.














Visual Weed Control




Compound A

(%) - 19 DAA



Benzyl Ester
Indanofan
LEFCH












gae/ha
gai/ha
Obs
Exp
















8
0
0
—



16
0
0
—



32
0
15
—



0
37.5
10
—



0
75
20
—



0
150
95
—



8
37.5
15
10



16
37.5
25
10



32
37.5
25
24



8
75
30
20



16
75
20
20



32
75
60
32



8
150
100
95



16
150
40
95



32
150
100
96

















TABLE 46







Synergistic Activity of In-Water Applications of Compound


A Benzyl Ester and Mefenacet Herbicidal Compositions


on Weed Control in a Rice Cropping System.














Visual Weed Control




Compound A

(%) - 21 DAA



Benzyl Ester
Mefenacet
ECHOR












gae/ha
gai/ha
Obs
Exp
















8
0
75
—



16
0
95
—



32
0
100
—



0
300
80



0
600
100



0
1200
100



8
300
100
48



16
300
99
64



32
300
100
74



8
600
100
68



16
600
100
78



32
600
100
84



8
1200
100
84



16
1200
100
89



32
1200
100
92

















TABLE 47







Synergistic Activity of In-Water Applications of Compound


A Benzyl Ester and Molinate Herbicidal Compositions


on Weed Control in a Rice Cropping System.














Visual Weed Control




Compound A

(%) - 21 DAA



Benzyl Ester
Molinate
ECHOR












gae/ha
gai/ha
Obs
Exp
















8
0
25
—



16
0
30
—



32
0
45
—



0
1400
55
—



0
2800
85
—



8
1400
65
66



16
1400
75
69



32
1400
90
75



8
2800
90
89



16
2800
99
90



32
2800
99
92

















TABLE 48





Synergistic Activity of In-Water Applications of Compound


A Benzyl Ester and Thenylchlor Herbicidal Compositions


on Weed Control in a Rice Cropping System.



















Visual Weed Control


Compound A

(%) - 19 DAA










Benzyl Ester
Thenylchlor
ECHOR
LEFCH












gae/ha
gai/ha
Obs
Exp
Obs
Exp





8
0
30
—
0
—


16
0
95
—
0
—


32
0
70
—
15
—


0
135
35
—
15
—


0
270
90
—
25
—


8
135
99
55
60
15


16
135
95
97
30
15


32
135
95
81
50
28


8
270
99
93
20
25


16
270
99
100 
80
25


32
270
99
97
90
36












CYPRO
Cyperus rotundus L.
nutsedge, purple


ECHCG
Echinochloa crusgalli (L.) Beauv.
barnyardgrass


ECHOR
Echinochloa oryzoides (Ard.) Fritsch
watergrass, early


FIMMI
Fimbristylis miliacea (L.) Vahl
fringerush, globe


LEFCH
Leptochloa chinensis (L.) Nees
sprangletop, Chinese


SCPJU
Schoenoplectus juncoides (Roxb.) Palla
bulrush, Japanese





gae/ha = grams acid equivalent per hectare


gai/ha = grams active ingredient per hectare


Obs = observed value


Exp = expected value as calculated by Colby's equation


DAA = days after application






Example III
Evaluation of Post-Emergence Foliar-Applied Herbicidal Mixtures for Weed Control in Cereal Crops in the Greenhouse
Seeds of the desired test plant species were planted in Sun Gro MetroMix® 306 planting mixture, which typically has a pH of 6.0 to 6.8 and an organic matter content of about 30 percent, in plastic pots with a surface area of 103.2 square centimeters (cm2). When required to ensure good germination and healthy plants, a fungicide treatment and/or other chemical or physical treatment was applied. The plants were grown for 7-36 days in a greenhouse with an approximate 14 hour photoperiod which was maintained at about 18° C. during the day and 17° C. during the night. Nutrients and water were added on a regular basis and supplemental lighting was provided with overhead metal halide 1000-Watt lamps as necessary. The plants were employed for testing when they reached the second or third true leaf stage.
Treatments consisted of the benzyl ester of 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)pyridine-2-carboxylic acid (Compound A), formulated as an SC (suspension concentrate), and a second cereal herbicide alone and in combination.
Forms of compound A (compound of formula I) tested include:




Measured aliquots of the benzyl ester of 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)pyridine-2-carboxylic acid (Compound A) were placed in 25 milliliter (mL) glass vials and diluted in a volume of 1.25% (v/v) Agri-dex crop oil concentrated to obtain stock solutions. Compound requirements are based upon a 12 mL application volume at a rate of 187 liters per hectare (L/ha). Spray solutions of the second cereal herbicide and experimental compound mixtures were prepared by adding the stock solutions to the appropriate amount of dilution solution to form 12 mL spray solution with active ingredients in two- and three-way combinations. Formulated compounds were applied to the plant material with an overhead Mandel track sprayer equipped with an 8002E nozzle calibrated to deliver 187 L/ha over an application area of 0.503 square meters (m2) at a spray height of 18 inches (46 cm) above average plant canopy. Control plants were sprayed in the same manner with the solvent blank.
The treated plants and control plants were placed in a greenhouse as described above and watered by sub-irrigation to prevent wash-off of the test compounds. After 20-22 days, the condition of the test plants as compared with that of the control plants was determined visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury and 100 corresponds to complete kill.
Colby's equation was used to determine 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 equation was used to calculate the expected activity of mixtures containing two active ingredients, A and B:

Expected=A+B−(A×B/100)

A=observed efficacy of active ingredient A at the same concentration as used in the mixture.
B=observed efficacy of active ingredient 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 49-50.







TABLE 49





Synergistic Activity of Foliar-Applied Compound A


Benzyl Ester and Flufenacet Herbicidal Compositions


on Weed Control in a Cereal Cropping System.

















Compound




A Benzyl

Visual Weed Control (%) - 21 DAA











Ester
Flufenacet
CIRAR
KCHSC
PAPRH














gai/ha
gai/ha
Obs
Exp
Obs
Exp
Obs
Exp





2.5
0
48
—
20
—
48
—


5
0
39
—
41
—
28
—


10
0
60
—
62
—
35
—


0
60
0
—
5
—
0
—


0
120
0
—
5
—
5
—


0
240
17
—
17
—
7
—


2.5
60
53
48
63
24
50
48


2.5
120
48
48
70
24
63
50


5
60
60
39
55
44
40
28


5
120
63
39
73
44
73
32


5
240
70
49
84
51
43
33


10
240
80
67
86
68
84
39












Compound




A Benzyl

Visual Weed Control (%) - 21 DAA










Ester
Flufenacet
SASKR
STEME












gai/ha
gai/ha
Obs
Exp
Obs
Exp





2.5
0
15
—
25
—


5
0
50
—
25
—


10
0
67
—
27
—


0
60
5
—
0
—


0
120
5
—
5
—


0
240
13
—
42
—


2.5
60
38
19
75
25


2.5
120
50
19
68
29


5
60
68
53
78
25


5
120
63
53
83
29


5
240
77
57
72
56


10
240
85
71
73
57












Compound




A Benzyl

Visual Weed Control (%) - 21 DAA










Ester
Flufenacet
CHEAL
SINAR












gai/ha
gai/ha
Obs
Exp
Obs
Exp





2.5
0
50
—
70
—


5
0
58
—
73
—


0
60
0
—
5
—


0
120
0
—
8
—


2.5
60
75
50
83
72


2.5
120
75
50
88
72


5
60
83
58
84
74


5
120
80
58
85
75
















TABLE 50





Synergistic Activity of Foliar-Applied Compound A


Benzyl Ester and Prosulfocarb Herbicidal Compositions


on Weed Control in a Cereal Cropping System.

















Compound




A Benzyl

Visual Weed Control (%) - 21 DAA










Ester
Prosulfocarb
GALAP
KCHSC












gai/ha
gai/ha
Obs
Exp
Obs
Exp





2.5
0
55
—
20
—


5
0
66
—
41
—


10
0
77
—
62
—


0
1000
15
—
10
—


0
2000
40
—
15
—


0
4000
67
—
75
—


2.5
1000
78
62
65
28


2.5
2000
78
73
73
32


5
1000
88
71
75
47


5
2000
88
80
78
50


5
4000
93
89
88
85


10
4000
94
92
92
90












Compound




A Benzyl

Visual Weed Control (%) - 21 DAA











Ester
Prosulfocarb
PAPRH
SASKR
STEME














gai/ha
gai/ha
Obs
Exp
Obs
Exp
Obs
Exp





2.5
0
48
—
15
—
25
—


5
0
28
—
50
—
25
—


10
0
35
—
67
—
27
—


0
1000
5
—
5
—
0
—


0
2000
10
—
5
—
10
—


0
4000
13
—
63
—
73
—


2.5
1000
48
50
45
19
50
25


2.5
2000
50
53
65
19
58
33


5
1000
85
32
58
53
55
25


5
2000
60
35
73
53
35
33


5
4000
63
38
80
82
91
80


10
4000
93
44
85
88
81
80












Compound




A Benzyl

Visual Weed Control (%) - 21 DAA










Ester
Prosulfocarb
CHEAL
SINAR












gai/ha
gai/ha
Obs
Exp
Obs
Exp





2.5
0
50
—
70
—


5
0
58
—
73
—


0
1000
10
—
13
—


0
2000
15
—
18
—


2.5
1000
83
55
88
74


2.5
2000
75
58
83
75


5
1000
83
62
86
76


5
2000
88
64
89
77























CHEAL
Chenopodium album L.
lambsquarters, common


CIRAR
Cirsium arvense (L.) Scop.
thistle, Canada


GALAP
Galium aparine L.
cleavers, catchweed bedstraw


KCHSC
Kochia scoparia (L.) Schrad.
kochia


PAPRH
Papaver rhoeas L.
poppy, common


SASKR
Salsola tragus L.
thistle, Russian


SINAR
Sinapis arvensis L.
mustard, wild


STEME
Stellaria media (L.) Vill.
chickweed, common









Example IV
Evaluation of Pre-emergence Soil-Applied Herbicidal Mixtures for Weed Control
Seeds or nutlets of the desired test plant species were planted in a soil matrix prepared by mixing a loam soil (32 percent silt, 23 percent clay, and 45 percent sand, with a pH of about 6.5 and an organic matter content of about 1.9 percent) and calcareous grit in an 80 to 20 ratio. The soil matrix was contained in plastic pots with a volume of 1 quart and a surface area of 83.6 square centimeters (cm2).
Treatments consisted of the benzyl ester of 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)pyridine-2-carboxylic acid (compound A) formulated as an SC (suspension concentrate) and various herbicidal components alone and in combination. Forms of compound A were applied on an acid equivalent basis.
Forms of compound A (compound of formula I) tested include:




Other herbicidal components were applied on an active ingredient basis and included very long chain fatty acid (VLCFA) synthesis-inhibiting and fatty acid/lipid synthesis-inhibiting herbicides alachlor (technical grade material), dimethenamid-P formulated as Outlook®, and S-metolachlor formulated as Dual® II Magnum.
Treatment requirements were calculated based upon the rates being tested, the concentration of active ingredient or acid equivalent 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 concentrate (COC) to obtain 12× 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) COC so that the final spray solutions contained 1.25% (v/v) COC.
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 12× 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) COC so that the final spray solutions contain 1.25% (v/v) COC. 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 12× 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) COC or water to obtain 12× 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) COC so that the final spray solutions contained 1.25% (v/v) COC. 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.
All stock solutions and applications solutions were visually inspected for compound compatibility prior to application. Spray solutions were applied to the soil 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 inches (46 cm) above average pot height. Control pots were sprayed in the same manner with the solvent blank.
The treated and control pots were placed in a greenhouse and top watered as needed. When required to ensure good germination and healthy plants, a fungicide treatment and/or other chemical or physical treatment was applied. The pots were maintained 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) were applied in the irrigation solution as needed and water was added on a regular basis. Supplemental lighting was provided with overhead metal halide 1000-Watt lamps as necessary. After approximately 4 weeks, the condition of the test plants as compared with that of the untreated plants was determined visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury or growth inhibition and 100 corresponds to complete kill.
Colby's equation was used to determine 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 equation was used to calculate the expected activity of mixtures containing two active ingredients, A and B:

Expected=A+B−(A×B/100)

A=observed efficacy of active ingredient A at the same concentration as used in the mixture.
B=observed efficacy of active ingredient 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 51-53.







TABLE 51







Synergistic Activity of Soil-applied, Pre-emergence


Applications of Compound A Benzyl Ester and Alachlor


Herbicidal Compositions on Weed Control














Visual Weed Control




Compound A

(%) - 27 DAA



Benzyl Ester
Alachlor
IPOHE












gae/ha
gai/ha
Obs
Exp
















32
0
28
—



0
1240
5
—



0
2480
13
—



32
1240
35
31



32
2480
55
37

















TABLE 52







Synergistic Activity of Soil-applied, Pre-emergence


Applications of Compound A Benzyl Ester and Dimethenamid-P


Herbicidal Compositions on Weed Control














Visual Weed Control




Compound A

(%) - 29 DAA



Benzyl Ester
Dimethenamid-P
XANST












gae/ha
gai/ha
Obs
Exp
















32
0
5
—



0
410
23
—



0
820
30
—



0
1640
50
—



32
410
48
26



32
820
43
34



32
1640
68
53

















TABLE 53





Synergistic Activity of Soil-applied, Pre-emergence


Applications of Compound A Benzyl Ester and S-Metolachlor


Herbicidal Compositions on Weed Control






















Visual Weed Control




Compound A

(%) - 28 DAA



Benzyl Ester
S-metolachlor
IPOHE












gae/ha
gai/ha
Obs
Exp







16
0
13
—



32
0
23
—



0
387.5
25
—



0
775
0
—



0
1550
33
—



16
387.5
48
34



32
387.5
53
42



16
775
45
13



32
775
38
23



16
1550
65
41



32
1550
53
48













IPOHE
Ipomoea hederacea (L.) Jacq.
morningglory, ivyleaf


XANST
Xanthium strumarium L.
cocklebur, common





gae/ha = grams acid equivalent per hectare


gai/ha = grams active ingredient per hectare


Obs = observed value


Exp = expected value as calculated by Colby's equation


DAA = days after application






Example V
Evaluation of Herbicidal Activity of Mixtures Applied Under Field Conditions to Transplanted Rice
Post and pre-emergence field trials were conducted in Niigata, Japan. Trial sites were located in commercially grown fields of transplanted rice (Oryza sativa, variety: Koshihikari) using standard herbicide small plot research methodology. The trial plot size was 2 meters (m)×2 m with 3 replications. The nursery plants were grown in the greenhouse using practical methods and transplanted into the field at the 2.5-leaf stage on May 7, 2012. The row and in-row spaces were 30 cm and 17 cm, respectively. The crop was grown using normal cultural practices for fertilization, water management and maintenance to ensure good growth of the crop and the weeds.
Treatments consisted of the benzyl ester of 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid (Compound A) formulated as an SC (suspension concentrate) and various herbicidal components alone and in combination. Compound A benzyl ester was applied on an active ingredient basis. The herbicidal components were applied on an active ingredient basis and included very long chain fatty acid (VLCFA) synthesis-inhibiting and fatty acid/lipid biosynthesis herbicides pretilachlor formulated as a commercially available granular formulation and benfuresate formulated as a commercially available flowable formulation.
Compound A benzyl ester SC was once diluted in 100 mL water in the 200 mL bottle/plot to achieve the desired rates and applied by water injection. Water injection applications were made by hand as evenly as possible. Pretilachlor was applied by hand, and benfuresate was applied using a pipette to achieve the desired rates. Each compound in mixture treatments was applied separately and successively. Water depth was 3 cm at application. Treatments were rated at 25 and 40 days after application (DAA) for post and pre-emergence trials respectively as compared to the untreated control plants. Visual weed control was scored on a scale of 0 to 100 percent where 0 corresponds to no injury and 100 corresponds to complete kill.
All treatment results, both for the single product and mixtures, are an average of 3 replicates. The trial sites had naturally occurring populations of weeds. The weed spectrum included, but was not limited to, common barnyardgrass (Echinochloa crus-galli, ECHCG), monochoria (Monochoria vaginalis, MOOVA), Japanese bulrush (Scirpus juncoides, SCPJU), kuroguwai (Eleocharis kuroguwai, ELOKU), common falsepimpernel (Lindernia pyxidaria, LIDPY), Souchet tardif (Cyperus serotinus, CYPSE), small-flower flatsedge (Cyperus difformis, CYPDI), American waterwort (Elatine triandra, ELTTR), and swamp smartweed (Polygonum hydropiperoides, POLHP).
Colby's equation was used to determine 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 equation was used to calculate the expected activity of mixtures containing two active ingredients, A and B:

Expected=A+B−(A×B/100)

A=observed efficacy of active ingredient A at the same concentration as used in the mixture.
B=observed efficacy of active ingredient B at the same concentration as used in the mixture.
Some of the compounds tested, application rates employed, plant species tested, and results for submerged (weeds have not yet emerged from the flood water) weed control are given in Table 54.
Some of the compounds tested, application rates employed, plant species tested, and results for early postemergence weed control are given in Tables 55-56.







TABLE 54







Synergistic Activity of In-Water Applied Compound A Benzyl


Ester and Benfuresate Herbicidal Compositions on Submerged


Weed Control in a Transplanted Rice Cropping System when


Evaluated 31 DAA (Days After Application) in Japan.











Visual Weed Control


Compound A

(%) - 31 DAA










Benzyl Ester
Benfuresate
SCPJU
POLHP












gai/ha
gai/ha
Obs
Exp
Obs
Exp















100
0
87.7
—
68.3
—


0
600
64.3
—
94.3
—


100
600
99.7
95.6
100.0
98.2
















TABLE 55







Synergistic Activity of In-Water Applied Compound A Benzyl Ester


and Benfuresate Herbicidal Compositions on Early Post-emergence


Weed Control in a Transplanted Rice Cropping System when Evaluated


11-16 DAA (Days After Application) in Japan.









Visual Weed Control



(%) - 11 & 16 DAA










Compound A

ECHCG
ECHCG


Benzyl Ester
Benfuresate
(11 DAA)
(16 DAA)












gai/ha
gai/ha
Obs
Exp
Obs
Exp















100
0
3.3
—
20.0
—


0
600
6.7
—
20.0
—


100
600
82.3
9.8
89.3
36.0
















TABLE 56





Synergistic Activity of In-Water Applied Compound A Benzyl Ester


and Pretilachlor Herbicidal Compositions on Early Post-emergence


Weed Control in a Transplanted Rice Cropping System when Evaluated


11 DAA (Days After Application) in Japan.






















Visual Weed Control




Compound A

(%) - 11 DAA



Benzyl Ester
Pretilachlor
ECHCG












gai/ha
gai/ha
Obs
Exp







100
0
6.7
—



0
400
46.7
—



100
400
89.3
50.3













ECHCG
Echinochloa crusgalli (L.) Beauv.
barnyardgrass


POLHP
Polygonum hydropiperoides Michx.
smartweed, swamp


SCPJU
Schoenoplectus juncoides (Roxb.) Palla
bulrush, Japanese





gai/ha = grams active ingredient per hectare


Obs = observed value


Exp = expected value as calculated by Colby's equation


DAA = days after application

## Claims

1. A herbicidal composition comprising a herbicidally effective amount of (a) a compound of the formula (I)



or C1-4 alkyl or benzyl ester thereof and (b) at least one herbicide, wherein the at least one herbicide inhibits very long chain fatty acid and fatty acid synthesis, wherein (b) is selected from the group consisting of: acetochlor, alachlor, anilofos, benfuresate, cafenstrole, dimethenamid-P, fentrazamide, indanofan, flufenacet, mefenacet, s-metolachlor, molinate, pethoxamid, pretilachlor, prosulfocarb, pyroxasulfone, thenylchlor, butachlor, and thiobencarb, or an agriculturally acceptable salt thereof, wherein (a) and (b) are present in the composition in a ratio such that the composition exhibits herbicidal synergy, and wherein the ratio between (a):(b) is from about 1:1 to about 1:800.

2. The composition of claim 1, wherein (a) is a C1-4 alkyl ester of compound (I).

3. The composition of claim 1, wherein (a) is a benzyl ester of compound (I).

4. The composition of claim 1, wherein (a) is the compound of formula (I), which is the carboxylic acid.

5. The composition of claim 1, further comprising at least one compound selected from the group consisting of agriculturally acceptable herbicide safeners, adjuvants, and carriers.

6. The composition according to claim 1, wherein the ratio between (a):(b) is selected from the group consisting of: from about 1:46 to about 1:3 when (b) is acetochlor; from about 1:78 to about 1:39 when (b) is alachlor; from about 1:50 to about 1:3 when (b) is anilofos; from about 1:57 to about 1:2 when (b) is benfuresate; from about 1:24 to about 1:2 when (b) is cafenstrole; from about 1:51 to about 1:9 when (b) is dimethenamid-P; from about 1:19 to about 1:1 when (b) is fentrazamide; from about 1:19 to about 1:2 when (b) is indanofan; from about 1:94 to about 1:12 when (b) is flufenacet; from about 1:150 to about 1:2 when (b) is mefenacet; from about 1:97 to about 1:12 when (b) is s-metolachlor; from about 1:350 to about 1:44 when (b) is molinate; from about 1:153 to about 1:38 when (b) is pethoxamid; from about 1:34 to about 1:2 when (b) is pretilachlor; from about 1:800 to about 1:200 when (b) is prosulfocarb; from about 1:15 to about 1:4 when (b) is pyroxasulfone; from about 1:34 to about 1:4 when (b) is thenylchlor; from about 1:6 to about 1:103 when (b) is butachlor, and from about 1:511 to about 1:32 when (b) is thiobencarb, and wherein any aforementioned compound for (b) may be an agriculturally acceptable salt thereof.

7. The composition of claim 1, wherein (b) is selected from the group consisting of: acetochlor, alachlor, anilofos, benfuresate, cafenstrole, dimethenamid-P, fentrazamide, indanofan, flufenacet, mefenacet, s-metolachlor, molinate, pethoxamid, pretilachlor, prosulfocarb, pyroxasulfone, thenylchlor, and thiobencarb, or an agriculturally acceptable salt thereof.

8. A method of controlling undesirable vegetation, comprising the steps of: contacting a plant, wherein the plant is undesirable vegetation, or the locus thereof, soil or water, wherein the soil or the water allows for the growth of the undesirable vegetation, with a herbicidally effective amount of a combination comprising (a) a compound of the formula (I):



or C1-4 alkyl or benzyl ester thereof and (b) at least one herbicide, wherein the at least one herbicide inhibits very long chain fatty acid and fatty acid synthesis, wherein (b) is selected from the group consisting of: acetochlor, alachlor, anilofos, benfuresate, cafenstrole, dimethenamid-P, fentrazamide, indanofan, flufenacet, mefenacet, s-metolachlor, molinate, pethoxamid, pretilachlor, prosulfocarb, pyroxasulfone, thenylchlor, butachlor, and thiobencarb, or an agriculturally acceptable salt thereof, wherein (a) and (b) are present in the composition in a ratio such that the composition exhibits herbicidal synergy, and wherein the ratio between (a):(b) is from about 1:1 to about 1:800.

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

10. The method of claim 8, wherein the (a) and (b) are applied to water.

11. The method of claim 10 wherein the water is part of a flooded rice paddy.

12. The method of claim 8, wherein the (a) and (b) are applied pre-emergently to undesirable vegetation.

13. The method of claim 8, wherein the (a) and (b) are applied post-emergently to undesirable vegetation.

14. The method of claim 8, wherein the undesirable vegetation is controlled in glyphosate-, 5-enolpyruvylshikimate-3-phosphate synthase inhibitor-, glufosinate-, glutamine synthetase inhibitor-, dicamba-, phenoxy auxin-, pyridyloxy auxin-, synthetic auxin-, auxin transport inhibitor-, aryloxyphenoxypropionate-, cyclohexanedione-, phenylpyrazoline-, acetyl CoA carboxylase inhibitor-, imidazolinone-, sulfonylurea-, pyrimidinylthiobenzoate-, triazolopyrimidine-, sulfonylaminocarbonyltriazolinone-, acetolactate synthase or acetohydroxy acid synthase inhibitors-, 4-hydroxyphenyl-pyruvate dioxygenase inhibitor-, phytoene desaturase inhibitor-, carotenoid biosynthesis inhibitor-, protoporphyrinogen oxidase 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-tolerant crops.

15. The method of claim 13, wherein the undesirable vegetation possesses multiple or stacked traits conferring tolerance to multiple herbicides or herbicides that exhibit multiple modes of action.

16. The method of claim 8, wherein the undesirable vegetation comprises a herbicide resistant or tolerant weed.

17. The method of claim 15, wherein the undesirable vegetation is a biotype with resistance or tolerance to multiple herbicides, multiple chemical classes, multiple herbicide modes-of-action or via multiple resistance mechanisms.

18. The method of claim 15, wherein the undesirable vegetation is a biotype resistant or tolerant to acetolactate synthase or acetohydroxy acid synthase inhibitors, photosystem II inhibitors, acetyl CoA carboxylase inhibitors, synthetic auxins, auxin transport inhibitors, photosystem I inhibitors, 5-enolpyruvylshikimate-3-phosphate synthase inhibitors, microtubule assembly inhibitors, fatty acid and lipid synthesis inhibitors, protoporphyrinogen oxidase inhibitors, carotenoid biosynthesis inhibitors, very long chain fatty acid inhibitors, phytoene desaturase inhibitors, glutamine synthetase inhibitors, 4-hydroxyphenyl-pyruvate-dioxygenase inhibitors, mitosis inhibitors, cellulose biosynthesis inhibitors, herbicides with multiple modes-of-action, quinclorac, arylaminopropionic acids, difenzoquat, endothall, or organoarsenicals.

19. The method according to claim 8, wherein the ratio between (a):(b) is selected from the group consisting of: from about 1:46 to about 1:3 when (b) is acetochlor; from about 1:78 to about 1:39 when (b) is alachlor; from about 1:50 to about 1:3 when (b) is anilofos; from about 1:57 to about 1:2 when (b) is benfuresate; from about 1:24 to about 1:2 when (b) is cafenstrole; from about 1:51 to about 1:9 when (b) is dimethenamid-P; from about 1:19 to about 1:1 when (b) is fentrazamide; from about 1:19 to about 1:2 when (b) is indanofan; from about 1:94 to about 1:12 when (b) is flufenacet; from about 1:150 to about 1:2 when (b) is mefenacet; from about 1:97 to about 1:12 when (b) is s-metolachlor; from about 1:350 to about 1:44 when (b) is molinate; from about 1:153 to about 1:38 when (b) is pethoxamid; from about 1:34 to about 1:2 when (b) is pretilachlor; from about 1:800 to about 1:200 when (b) is prosulfocarb; from about 1:15 to about 1:4 when (b) is pyroxasulfone; from about 1:34 to about 1:4 when (b) is thenylchlor; from about 1:6 to about 1:103 when (b) is butachlor, and from about 1:511 to about 1:32 when (b) is thiobencarb, and wherein any aforementioned compound for (b) may be an agriculturally acceptable salt thereof.

20. The method according to claim 8, wherein (b) is selected from the group consisting of: acetochlor, alachlor, anilofos, benfuresate, cafenstrole, dimethenamid-P, fentrazamide, indanofan, flufenacet, mefenacet, s-metolachlor, molinate, pethoxamid, pretilachlor, prosulfocarb, pyroxasulfone, thenylchlor, and thiobencarb, or an agriculturally acceptable salt thereof.