OA17164A - Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl) pyridine-2-carboxylic acid - Google Patents

Abstract

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

Description

This patent application daims the benefit of United States provisional patent application number 61/675,056, filed on July 24,2012, and United States utility patent application number 13/833,315, filed on March 15,2013 each of which is incorporated herein by reference in its entirety.

Field

Provided herein are herbicidal compositions comprising (a) 4-amino-3-chloro-5fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl) pyridine-2-carboxylîc acid or an âgriculturally acceptable ester or sait thereof and (b) clomazone. Provided herein are also methods of controlling undesirable végétation comprising applying (a) 4-amino-3-chIoro-5-fluoro-6-(4chloro-2-fluoro-3-methoxyphenyI)pyridine-2-carboxylic acid or an agriculturally acceptable ester or sait thereof and (b) clomazone.

Background

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

» Summarv

A first embodiment of the invention provided herein includes herbicidal compositions comprising an herbicidally effective amount of (a) a compound of the formula (I)

H<° (» or an agriculturally acceptable sait or ester thereof, and (b) clomazone.

A second embodiment includes the mixture of the first embodiment in which formula (I) îs présent in at least one of the following forms: a carboxylic acid, a carboxylate sait, an aralkyl, an alkyl ester, an unsubstituted benzyl, a substituted benzyl, aCm alkyl, an n-butyl ester or a benzyl ester.

A third embodiment includes the mixture according to the first or second embodiments wherein the weight ratio of the compound of formula (I) to clomazone given in units of gae/ha to gai/ha or gae/ha to gae/ha is selected from the group of ranges of ratios and ratios consisting of: from about 1:153 to 1:0.8,1:12.8,1:25.6, 1:51.1,1:3.2,1:6.4,1:14,1:28, 1:38,1:6.25, 1:20, 1:7, 1:14,1:26, 1:12,8,1:84, and 1:773 to 6:1

A fourth embodiment includes methods of controlling undesirable végétation comprising the step of applying or otherwise contacting végétation and/or soi!, and/ or water with a herbicidally effective amount of at least one mixture according to the first through the third embodiments.

A fîfth embodiment includes methods according to the fourth embodiment wherein undesirable végétation is controlled by practicing at least one of the methods in at least one member of the group consisting of: in direct-seeded, water-seeded, and/or transplanted rice, cereals, wheat, barley, oats, rye, sorghum, com/maize, sugarcane, sunflower, oilseed râpe, canola, sugar beet, soybean, cotton, pineapple, pastures, grasslands, rangelands, fallowland, turf, tree and vine orchards, aquatics, plantation crops, vegetables, industrial végétation management (IVM), or rights-of-way (ROVV).

A sixth embodiment includes methods according to the fourth and/or fîfth embodiments wherein a herbicidally effective amount of the mixture is applied either pre- or post-emergently to at least one of the following: a crop, a field, a ROW, or a rice paddy.

A seventh embodiment includes methods according to the fourth through the sixth embodiments wherein the undesirable végétation may be controlled by practicing at least one of the methods in plants that are résistant or tolérant to at least one agent or an agent that acts by at least one mode of action selected from the group consisting of: in glyphosate-, 5enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitor-, glufosinate-, glutamine synthetase inhibitor-, dicamba-, phenoxy auxin-, pyridyloxy auxin-, synthetic auxin-, auxin transport inhibitor-, aryloxyphenoxypropionate-, cyclohexanedione-, phenylpyrazoline-, acetyl CoA carboxylase (ACCase) inhibitor-, imidazolinone-, sulfonylurea-, pyrimidinylthiobenzoate-, triazolopyrimidine-, sulfonylaminocarbonyltriazolinone-, acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) iinhibitor-, 4hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor-, phytoene desaturase inhibitor-, carotenoid biosynthesis inhibitor-, protoporphyrinogen oxidase (PPO) inhibitor-, cellulose biosynthesis inhibitor-, mitosis inhibitor-, microtubule inhibitor-, very long chain fatty acid inhibitor-, fatty acid and lipid biosynthesis inhibitor-, photosystem I inhibitor-, photosystem II inhibitor-, protoporphyrinogen oxidase (PPO) inhibitor-, triazine-, or bromoxynil.

An eighth embodiment includes a at least one method according to the fourth through the seventh embodiments wherein a plant that is résistant or tolérant to at least one herbicide is treated, and where the résistant or tolérant crop possesses multiple or stacked traits conferring tolérance to multiple herbicides or inhibitors of multiple herbicide modes of action, in some embodiments the treated plant that expresses résistance to a herbicide is a itself undesirable végétation.

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

A tenth embodiment includes at least one of the methods according to the eighth or ninth embodiments, wherein the résistant or tolérant undesirable plant is a biotype résistant or tolérant to at least one agent that acts by at least one mode of action selected from the group consisting of: acetolactate synthase (ALS) inhibitors or acetohydroxy acid synthase (AHAS), photosystem II inhibitors, acetyl CoA carboxylase (ACCase) inhibitors, synthetic auxins, auxîn transport inhibitors, photosystem I inhibitors, 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, microtubule assembly inhibitors, fatfy acid and lîpid synthesis inhibitors, protoporphyrinogen oxîdase (PPO) inhibitors, carotenoid biosynthesis inhibitors, very long chain fatty acid (VLCFA) inhibitors, phytoene desaturase (PDS) inhibitors, glutamine synthetase inhibitors, 4-hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitors, mitosis inhibitors, cellulose biosynthesis inhibitors, herbicides with multiple modes-of-action, quinclorac, arylaminopropionic acids, difenzoquat, endothall, or organoarsenicals.

An eleventh embodiment includes methods of controlling undesirable végétation comprising the step of applying a herbicidally effective amount of at least one mixture according to the first or second embodiments wherein the amount of the mixture is applied at a rate, expressed in ai/ha of clomazone selected from the group of rates and ranges of rates consisting of, about: 1,2,25,56, 112,224,448,670, 840, and the range 1:1000.

A twelfth embodiment includes methods according to the first, third, and eleventh embodiments wherein the controlled plant is at least one plant selected from the group consisting of: DIGSA, LEFCH, IPOHE, ECHCG, ECHCO, CYPRO, CYPDI, and SCPMA, still other embodiments include controlling plants from the généra consisting of: Dlgitaria, Lcptochloa, Ipomoea, Echinochloa, Bolboschoenus, and Cyperus.

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

or an agriculturally acceptable sait or ester of thereof, and (b) clomazone. The compositions may also contain an agriculturally acceptable adjuvant or carrier.

Provided herein are also methods of controlling undesirable végétation comprising applying (a) a compound of formula (I) or an agriculturally acceptable ester or sait thereof and (b) clomazone or an agriculturally acceptable sait or ester thereof.

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

As used herein, clomazone is 2-[(2-chlorophenyl)methyl]-4,4-dimethyl-3isoxazolidinone and possesses the following structure:

O

Its herbicidal activity is exemplified in Tomlin, C., ed. A Worid Compendium The Pesticide Manual. I5^lhed. Alton: BCPC Publications, 2009. Exemplary uses of clomazone include its use for pre-emergence, pre-plant incorporated, or very early post-emergence control of small-seeded broadleaf and annual grass weeds, e.g., in rice, soybean, peas, maize, oilseed râpe, sugar cane, cassava, pumpkins, potatoes, tobacco and other vegetables. Clomazone can be applied, e.g., pre-plant incorporated or pre-emergence to the soil, or as an early post-emergence treatment to undesirable végétation. As another example, clomazone can be applied pre-emergence to the soil before or after planting rice and into flooded rice paddies/fields to control, e.g., annual grasses.

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

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

As used herein, controlling undesirable végétation means preventing, reducing, killing, or otherwise adversely modifying the development of plants and végétation.

Described herein are methods of controlling undesirable végétation through the application of certain herbicide combinations or compositions. Methods of application include, but are not limited to applications to the végétation or locus thereof, e.g., application to the area adjacent to the végétation, as well as pre-emergence, post-emergence, foliar (broadcast, directed, 20 banded, spot, mechanical, over-the-top, or rescue), and in-water applications (emerged and submerged végétation, broadcast, spot, mechanical, water-injected, granular broadcast, granular spot, shaker bottle, or stream spray) via hand, backpack, machine, tractor, or aerial (airplane and helicopter) application methods.

As used herein, plants and végétation include, but are not limited to, germinant seeds, 25 emerging seedlings, plants emerging from végétative propagules, immature végétation, and established végétation.

As used herein, agriculturally acceptable salts and esters refer to salts and esters that exhibit herbicidal actîvity, 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 30 hydrolyzed, oxidized, metabolized, or otherwise converted, e.g., in plants, water, or soil, to the corresponding carboxylic acid which, dependîng on the pH, may be in the dissociated or undissociated form.

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

r’r^r⁴^ wherein R¹, R², R³ and R⁴ each, independently represents hydrogen or C|-Ct₂ alkyl, C₃-C|₂ alkenyl or C₃-Cj₂ alkynyl, each of which is optionally substituted by one or more hydroxy, C1-C4 alkoxy, C1-C4 alkylthio or phenyl groups, provided that R¹, R², R³ and R⁴ are sterically compatible. Additionally, any two of R¹, R², R³ and R⁴ together may represent an aliphatic difunctional moiety containing one to twelve carbon atoms and up to two oxygen or sulfur atoms. Salts can be prepared by treatment with a métal hydroxide, such as sodium hydroxide, with an amine, such as ammonia, trimethylamine, diethanolamine, 2-methylthiopropylamine, bisallylamine, 2-butoxyethylamine, morpholine, cyclododecylamine, or benzylamine or with a tetraalkylammonium hydroxide, such as tétraméthylammonium hydroxide or choline hydroxide.

Exemplary esters include those derived from Ci-C₎₂ alkyl, C₃-C|₂ alkenyl, C₃-C|₂ 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 transestérification.

Compositions and Methods

Provided herein are herbicidal compositions comprising a herbicidally effective

amount of (a) a compound of the formula (I)
R	nh2 tV
(TV	ΛΖγ0Η
	_ ο
cr γ	F
H1C°	(I)

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

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

Furthermore, in some embodiments, the combination of compound (1) or agriculturally acceptable sait or ester thereof and clomazone exhibits synergism, e.g., the herbicidal active ingrédients are more effective in combination than when applied individually. Synergism has been defined as “an interaction of two or more factors such that the effect when combined is greater than the predicted effect based on the response of each factor applied separately.” Senseman, S., ed. Herbicide Handbook. 9^,h ed. Lawrence: Weed Science Society of America, 2007. In certain embodiments, the compositions exhibit synergy as determined by the Colby’s équation. Colby, S.R. 1967. Calculation of the synergistic and antagonistic response of herbicide combinations. Weeds 15:20-22.

In certain embodiments of the compositions and methods described herein, the compound of formula (I), i.e., the carboxylic acid, is employed. In certain embodiments, a carboxylate sait of the compound of formula (I) is employed. In certain embodiments, an aralkyl or alkyl ester is employed. In certain embodiments, a benzyl, substituted benzyl, or C[4 alkyl, e.g., n-butyl ester is employed. In certain embodiments, the benzyl ester is employed.

S

In some embodiments, the compound of formula (I) or sait or ester thereof and clomazone are formulated ïn 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 area adjacent to the plant at any stage of growth. The effect observed dépends upon the plant species to be controlled, the stage of growth of the plant, the application parameters of dilution and spray drop size, the particle size of solid components, the environmental conditions at the time of use, the spécifie compound employed, the spécifie adjuvants and carriers employed, the soil type, and the like, as well as the amount of chemical applied. These and other factors can be adjusted to promote non-selective or sélective herbicidal action. In some embodiments, the compositions described herein are applied as a post-emergence application, pre-emergence application, or in-water application to flooded paddy rice or water bodies (e.g., ponds, lakes and streams), to relatively immature undesirable végétation to achieve the maximum control of weeds.

In some embodiments, the compositions and methods provided herein are utilized to control weeds in crops, including but not limited to direct-seeded, water-seeded and transplanted rice, cereals, wheat, barley, oats, rye, sorghum, com/maize, sugarcane, sunflower, oilseed râpe, canola, sugar beet, soybean, cotton, pineapple, pastures, grasslands, rangelands, fallowland, turf, tree and vine orchards, aquatics, plantation crops, vegetables, industrial végétation management (IVM) and rights of way (ROW).

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

The compositions and methods described herein may be used to control undesirable végétation in glyphosate-tolerant-, 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitor-tolerant-, glufosinate-tolerant-, glutamine synthetase inhibitor-tolerant-, dicambatolerant-, phenoxy auxin-tolerant-, pyridyloxy auxin-tolerant-, auxin-tolerant-, auxin transport inhibitor-tolerant-, aryloxyphenoxypropionate-tolerant-, cyclohexanedione-tolerant-, phenylpyrazoline-tolerant-, acetyl CoA carboxylase (ACCase) inhibitor-tolerant-, imidazolinone-tolerant-, sulfonylurea-tolerant-, pyrimidinylthiobenzoate-tolerant-, tri azo lopyrimi dine-tolerant-, sul fonyl ami nocarbonyl triazol inone-tolerant-, acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitor-tolerant-, 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitor-tolerant-, phytoene desaturase inhibitor-tolerant-, carotenoid biosynthesis inhibitor-tolerant-, protoporphyrinogen oxidase (PPO) inhibitor tolérant-, cellulose biosynthesis inhibitor-tolerant-, mitosis inhibitor-tolerant-, microtubule inhibitor-tolerant-, very long chain fatty acid inhibitor-tolerant-, fatty acid and lipîd biosynthesis inhibitor-tolerant-, photosystem I inhibitor-tolerant-, photosystem II inhibitortolerant-, triazine-tolerant- and bromoxynil-tolerant-crops (such as, but not limited to, soybean, cotton, canola/oilseed râpe, rice, cereals, corn, sorghum, sunflower, sugar beet, sugarcane, turf, etc.), for example, in conjunction with glyphosate, EPSP synthase inhibitors, glufosinate, glutamine synthase inhibitors, dicamba, phenoxy auxins, pyridyloxy auxins, synthetic auxins, auxin transport inhibitors, aryloxyphenoxypropionates, cyclohexanediones, phenylpyrazolines, ACCase inhibitors, imidazolînones, sulfonylureas, pyrimidinylthiobenzoates, dimethoxy-pyrimidines, triazolopyrimîdine sulfonamides, sulfonylaminocarbonyltriazolinones, ALS or AHAS inhibitors, HPPD inhibitors, phytoene desaturase inhibitors, carotenoid biosynthesis inhibitors, PPO inhibitors, cellulose biosynthesis inhibitors, mitosis inhibitors, microtubule inhibitors, very long chain fatty acid inhibitors, fatty acid and lipîd biosynthesis inhibitors, photosystem I inhibitors, photosystem II inhibitors, triazines, and bromoxynil. The compositions and methods may be used in controlling undesirable végétation in crops possessing multiple or stacked traits conferring tolérance to multiple chemistries and/or inhibitors of multiple modes of action. In some embodiments, the compound of formula (1) or sait or ester thereof and complementary herbicide or sait or ester thereof are used in combination with herbicides that are sélective for the crop being treated and which complément the spectrum of weeds controlled by these compounds at the application rate employed. In some embodiments, the compositions described herein and other complementary heibicides are applied at the same time, either as a combination formulation or as a tank mix, or sequentially.

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

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

In some embodiments, the methods provided herein are utilized to control undesirable végétation in rice. In certain embodiments, the undesirable végétation is Brachîaria 5 platyphylla (Groseb.) Nash or Urochloa platyphylla (Nash) R.D. Webster (broadleaf signalgrass, BRAPP), Digitaria sanguinalis (L.) Scop. (large crabgrass, DIGSA), Echinochloa species (ECHSS), Echinochloa cnis-galli (L.) P. Beauv. (bamyardgrass, ECHCG), Echinochloa crus~pavonis (Kunth) Schult. (gulf cockspur, ECHCV), Echinochloa colonum (L.) LINK (junglerice, ECHCO), Echinochloa oryzoides (Ard.) Fritsch (early 10 watergrass, ECHOR), Echinochloa oryzlcola (Vasînger) Vasinger (late watergrass, ECHPH), Echinochloa phyllopogon (Stapf) Koso-Pol. (rice bamyardgrass, ECHPH), Echinochloa polystachya (Kunth) Hitchc. (creeping river grass, ECHPO), Ischaemum nigosum Salisb. (saramollagrass, ISCRU), Leptochloa chinensis (L.) Nees (Chinese sprangletop, LEFCH), Leptochloa fascicularis (Lam.) Gray (bearded sprangletop, LEFFA), Leptochloa panicoides 15 (Presl.) Hitchc. (Amazon sprangletop, LEFPA), Oryza species (red and weedy rice, ORYSS), Panicum dichotomifiomm (L.) Michx. (fall panîcum, PANDI), Paspalum dilatation Poir. (dallisgrass, PASDI), Rottboellia cochinchinensis (Lour.) W.D. Clayton (itchgrass, ROOEX), Cypenis species (CYPSS), Cypenis dijformis L. (smallflower flatsedge, CYPDI), Cypenis dubius Rottb. (MAPDU), Cypenis esculentus L. (yellow nutsedge, CYPES), Cypenis iria L 20 (rice flatsedge, CYPIR), Cypenis rotundus L. (purple nutsedge, CYPRO), Cypenis serotinus RottbJC.B.Clarke (tidalmarsh flatsedge, CYPSE), Eleocharis species (ELOSS), Fimbristylis müiacea (L.) Vahl (globe fringerush, FIMMI), Schoenoplectus species (SCPSS), Schoenoplectiis juncoides Roxb. (Japanese bulrush, SCPJU), Bolboschoenus maritimus (L.) Palla or Schoenoplectus maritimus L. Lye (sea clubrush, SCPMA), Schoenoplectus 25 mucronatus L. (ricefield bulrush, SCPMU), Aeschynomene species, (jointvetch, AESSS), Altemanthera phlloxeroides (Mart.) Griseb. (alligatorweed, ALRPH), Alîsma plantagoaquatica 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 30 daisy, ECLAL), Heteranthera limosa (SW.) WilldWahl (ducksalad, HETL1), Heteranthera reniformis R. & P. (roundleaf mudplantain, HETRE), Ipomoea species (momingglories, IPOSS), Ipomoea hederacea (L.) Jacq. (ivyleaf momingglory, IPOHE), Lindernia dtibia (L.) Pennell (low false pimpemel, LIDDU), Ludwigia species (LUDSS), Ludwigia linifolia Poir. (southeastem primrose-willow, LUDLI), Ludwigia octovalvis (Jacq.) Raven (longfruited primrose-willow, LUDOC), Monochoria korsakowii Regel & Maack (monochoria, MOOKA), Monochoria vaginalis (Burm. F.) C. Presl ex Kuhth, (monochoria, MOOVA), Mtirdannîa nudiflora (L.) Brenan (doveweed, MUDNU), Polygonum pensylvanicum L., (Pennsylvania smartweed, POLPY), Polygonum persicaria L. (ladysthumb, POLPE), Polygonum hydroplperoldes Michx. (POLHP, mîld smartweed), Rotala indica (Willd.) Koehne (Indian toothcup, ROTIN), Sagitlaria species, (arrowhead, SAGSS), Sesbania exallata (Raf.) Cory/Rydb. Ex Hill (hemp sesbania, SEBEX), or Sphenoclea zeylanica Gaertn. (gooseweed, SPDZE).

In some embodiments, the methods provided herein are utilized to control undesirable végétation in cereals. In certain embodiments, the undesirable végétation is Alopeairus myosuroides Huds. (blackgrass, ALOMY), Apera spica-venti (L.) Beauv. (windgrass, APESV), Avenafatua L. (wild oat, AVEFA), Bromus tectorum L. (downy brome, BROTE), Loliiim multiflorum Lam. (Italian ryegrass, LOLMU), Phalaris mînor Retz, (littleseed canarygrass, PHAMI), Poa annua L. (annual bluegrass, POANN), Setaria ptimila (Poir.) Roemer & J.A. Schultes (yellow foxtail, SETLU), Setaria viridis (L.) Beauv. (green foxtail, SETVI), Amaranthus retroflexus L. (redroot pigweed, AMARE), Brasslca species (BRSSS), Chenopodium album L. (common lambsquarters, CHEAL), Cirsium arvense (L.) Scop. (Canada thîstle, CI RA R/ Galium aparine L. (catchweed bedstraw, GALAP), Kochia scoparia (L.) Schrad. (kochia, KCHSC), Lamiumpurpureum L. (purple deadnettle, LAMPU), Matricaria reaitita L. (wild chamomile, MATCH), Matricaria matricarioides (Less.) Porter (pîneappleweed, MATMT), Papaver rhoeas L. (common poppy, PAPRH), Polygonum convolvtilus L. (wild buckwheat, POLCO), Salsola tragus L. (Russian thîstle, SASKR), Sinapis species (SINSS), Sinapis arvensis L. (wild mustard, SINAR), Stellaria media (L.) Vill. (common chickweed, STEME), Veronicapersica Poir. (Persian speedwell, VERPE), Viola arvensis Murr. (field violet, V1OAR), or Γ/ο/α tricolor L. (wild violet, VIOTR).

In some embodiments, the methods provided herein are utilized to control undesirable végétation in range and pasture, fallowland, 1VM and ROW. In certain embodiments, the undesirable végétation is Ambrosia artemisiifolia L. (common ragweed, AMBEL), Cassia obtusifolia (sickle pod, CASOB), Centaurea maculosa auct. non Lam. (spotted knapweed, CENMA), Cirsium arvense (L.) Scop. (Canada thîstle, CIRAR), Convohmlus arvensis L. (field bindweed, CONAR), Douais carota L. (wild carrot, DAUCA), Euphorbia esula L. (leafy spurge, EPHES), Lactuca serriola L/Tom. (prickly lettuce, LACSE), Plantago lanceolata L. (buckhom plantain, PLALA), Rumex obtusifolius L. (broadleaf dock,

RUMOB), Sida spinosa L. (prickly sida, SIDSP), Sinapis arvensis L. (wild mustard, SINAR), Sonchus arvensis L. (perennial sowthistle, SONAR), Solidago species (goldenrod, SOOSS), Taraxacum officinale G.H. Weber ex Wiggers (dandelion, TAROF), Trifolium repens L. (white clover, TRFRE), or Urtica dioica L. (common nettle, URTDI).

In some embodiments, the methods provided herein are utilized to control undesirable végétation found in row crops, tree and vine crops, and perennial crops. In certain embodiments, the undesirable végétation is Alopecurus myosuroides Huds. (blackgrass, ALOMY), Avena fa tua 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. (southem sandbur, CENEC), Digitaria horizontalis Willd. (Jamaican crabgrass, DIGHO), Digitaria insularis (L.) Mez ex Ekman (sourgrass, TRCIN), Digitaria sanguinalis (L.) Scop. (large crabgrass, DIGSA), Echinochloa crtts-galli (L.) P. Beauv. (bamyardgrass, ECHCG), Echinochloa colonum (L.) Link (junglerice, ECHCO), Eletisine indica (L) Gaertn. (goosegrass, ELEIN), Lolium multiflorum Lam. (Italian ryegrass, LOLMU), Panicum dichotomifîorum Mîchx. (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), Cypertts esculentus L. (yellow nutsedge, CYPES), Cypertts rotundus L. (purple nutsedge, CYPRO), Abutilon theophrasti Medik. (velvetleaf, ABUTH), Amaranthus species (pigweeds and amaranths, AMASS), Ambrosia artemisiîfolia L. (common ragweed, AMBEL), Ambrosiapsilostachya DC. (western ragweed, AMBPS),/f mbrosia trifida L. (giant ragweed, AMBTR), Anoda cristata (L.) Schlecht. (spurred anoda, ANVCR), Asclepias syriaca L. (common milkweed, ASCSY), Bidenspilosa L. (hairy beggarticks, BIDPI), Borreria species (BOISS), Borreria alata (Aubl.) DC. or Spermacoce alata Aubl. (broadleaf buttonweed, BOILF), Spermacose latifolia (broadleaved button weed, BOILF), Chenopodium album L. (common lambsquarters, CHEAL), Cirsittm arvense (L.) Scop. (Canada thistle, CIRAR), Commelina benghalensis L. (tropical spiderwort, COMBE), Datura stramonium L. (jimsonweed, DATST), Dauctts carota L. (wild carrot, DAUCA), Euphorbia heterophylla L. (wild poinsettia, EPHHL), Ettphorbia 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), Helianthtis annuus L. (common sunflower, HELAN)> Jacquemontia tamnifolia (L.)

Griseb. (smallflower momingglory, IAQTA), Ipomoea hederacea (L.) Jacq. (ivyleaf momingglory, IPOHE), Ipomoea lacunosa L. (white momingglory, IPOLA), Lactuca serriola L/Tom. (prickly lettuce, LACSE), Portttlaca oleracea L. (common purslane, POROL), Richardia species (pusley, RCHSS), Sida species (sida, SIDSS), Sidaspinosa L. (prickly sida, SIDSP), Sinapis arvensis L. (wild mustard, SINAR), Solanumptychanthum

Dunal (eastem black nightshade, SOLPT), Tridaxprocumbens L. (coat buttons, TRQPR), or

Xanthium strumaritim L. (common cocklebur, XANST).

In s orne embodiments, the methods provided herein are utilized to control undesirable végétation in turf. In certain embodiments, the undesirable végétation is Bellisperennis L. (English daisy, BELPE), Cyperus esculentus L. (yellow nutsedge, CYPES), Cyperus species (CYPSS), Digitaria sanguinalis (L.) Scop. (large crabgrass, DIGSA), Diodia vîrginiana L.

(Virginia buttonweed, DIQVI), Euphorbia species (spurge, EPHSS), Glechoma hederacea L. (ground ivy, GLEHE), Hydrocotyle umbellata L. (dollarweed, HYDUM), Kyllinga species (kyllinga, KYLSS), Lamium amplexicaule L. (henbit, LAMAM), Murdannia nudiflora (L.) Brenan (doveweed, MUDNU), Oxalis species (woodsorrel, OXASS), Plantago major L.

(broadleaf plantain, PLAMA), Plantago lanceolata L. (buckhom/narrowleaf plantain,

PLALA), Phyllanthus tirinaria L. (chamberbitter, PYLTE), Rumex obtiisifolins L. (broadleaf dock, RUMOB), Stachys floridana Shuttlew. (Florida betony, STAFL), Stellaria media (L.) Vill. (common chickweed, STEME), Taraxacum officinale G.H. Weber ex Wiggers (dandelion, TAROF), Trifolium repens L. (white clover, TRFRE), or Viola species (wild violet, VIOSS).

In some embodiments, the compositions and methods provided herein are utilized to control undesirable végétation consisting of grass, broadleaf and sedge weeds. In certain embodiments, the compositions and methods provided herein are utilized to control undesirable grass, broadleaf and sedge végétation including but not limited to Bolboschoenus, 30 Cyperus, Digitaria, Echinochloa, Ipomoea, andLeptochloa,

In some embodiments, the combination of compound (I) or agriculturally acceptable ester or sait thereof and clomazone are used to control, including but not limited to large crabgrass (Digitaria sanguinalis), bamyardgrass (Echinochloa crus-galli), jungle rice (Echinochloa colona), ivyleaf momingglory (Ipomoea hederacea), Chinese sprangletop (Leptochloa chinensis), smallflower umbrella sedge (Cyperus difformis), purple nutsedge (Cyperus rotimdus) and sea clubrush (Bolboschoenus maritimus or Schoenoplectus maritimus).

The compounds of formula I or agriculturally acceptable sait or ester thereof may be used to control herbicide résistant or tolérant weeds. The methods employing the combination of a compound of formula I or agriculturally acceptable sait or ester thereof and the compositions described herein may also be employed to control herbicide résistant or tolérant weeds. Exemplary résistant or tolérant weeds include, but are not limited to, biotypes résistant or tolérant to acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) )0 inhibitors (e.g., imidazolînones, sulfonylureas, pyrimidinylthiobenzoates, dimethoxypyrimidines, triazolopyrimidine sulfonamides, sulfonylaminocarbonyltriazolinones), photosystem II inhibitors (e.g., phenylcarbamates, pyridazinones, triazines, triazinones, uracîls, amides, ureas, benzothiadiazinones, nitrites, phenylpyridazines), acetyl CoA carboxylase (ACCase) inhibitors (e.g., aryloxyphenoxypropionates, cyclohexanediones, phenylpyrazolines), synthetic auxins (e.g., benzoic acids, phenoxycarboxylic acids, pyridine «

carboxylîc acids, quinoline carboxylic acids), auxin transport inhibitors (e.g., phthalamates, semicarbazones), photosystem I inhibitors (e.g., bipyridyliums), 5-enolpyruvylshîkimate-3phosphate (EPSP) synthase inhibitors (e.g., glyphosate), glutamine synthetase inhibitors (e.g., glufosinate, bialafos), microtubule assembly inhibitors (e.g., benzamides, benzoic acids, dinitroanîlines, 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 oxîdase (PPO) inhibitors (e.g., diphenylethers, N-phenylphthalimides, oxadiazoles, oxazolidinediones, phenylpyrazoles, pyrimidindiones, thiadiazoles, triazolinones), carotenoid biosynthesis inhibitors (e.g., clomazone, amitrole, aclonifen), phytoene desaturase (PDS) inhibitors (e.g., amides, anîlidex, furanones, phenoxybutan-amîdes, pyridiazinones, pyridines), 4· hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitors (e.g., callistemones, isoxazoles, pyrazoles, triketones), cellulose biosynthesis inhibitors (e.g., nitrites, benzamides, quinclorac, triazolocarboxamides), herbicides with multiple modes-of-action such as quinclorac, and unclassified herbicides such as arylaminopropîonic acids, difenzoquat, endothall, and organoarsenicals. Exemplary résistant or tolérant weeds include, but are not limited to, biotypes with résistance or tolérance to multiple herbicides, biotypes with résistance or tolérance to multiple chemical classes, biotypes with résistance or tolérance to multiple herbicide modes-of-action, and biotypes with multiple résistance or tolérance mechanisms (e.g., target site résistance or metabolic résistance).

In certain embodiments of the compositions and methods described herein, the compound of formula (1) or sait or ester thereof is used in combination with clomazone.

With respect to the compositions, in some embodiments, the weight ratio of the compound of formula (1) or sait or ester thereof to clomazone is within the ranges of from about 1:773 to about 6:1 or from about 1:850 to about 3:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to clomazone is within the range of from about 1:153 to about 1:1 or about 1:32 to about 1:1. In certain embodiments, the weight ratio of the compound of formula (1) or sait or ester thereof to clomazone is within the range of from about 1:1.6 to about 1:52 or about 1:16 to about 1:10. In certain embodiments, the weight ratio of the compound of formula (1) or sait or ester thereof to clomazone is within the ranges of from about 1:1.6 to about 1:51, or 1:3.2 to about 1:51. In certain embodiments, the compositions provided herein comprise the compound of formula (1) or its benzyl ester and clomazone. In one embodiment, the composition comprises the compound of formula (1) and clomazone, wherein the weight ratios of the compound of formula (1) to clomazone is about 1:773 to about 6:1, or about 1:3.2 to about 1:56. In one embodiment, the composition comprises the benzyl ester of the compound of formula (1) and clomazone, wherein the weight ratio of the benzyl ester of the compound of formula (1) to clomazone is about 1:153 to about 1:1, or about 1:3.2 to about 1:56. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 52 or about 102 grams active ingrédient per hectare (gai/ha) to about 2,100 gai/ha based on the total amount of active ingrédients in the composition. In certain embodiments, the composition is applied at an application rate of from about 60 grams active ingrédient per hectare (gai/ha) to about 734 gai/ha or 110 gai/ha to about 1,000 gai/ha based on the total amount of active ingrédients in the composition. In some embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation with a compound of formula (1) or sait or ester thereof and clomazone, e.g., sequentially or sîmultaneously. In some embodiments, clomazone is applied at a rate from about 100 to about 1,700 or about 50 gai/ha to about 1,700 gai/ha and the compound of formula (1) ofsalt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, clomazone is applied at a rate from about 54 gai/ha to about 1,000 gai/ha or from about 28 gai/ha to about 448 gai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 g acid équivalent per hectare (gae/ha) to about 200 gae/ha or to about 706 gae/ha. In some embodiments, clomazone is applied at a rate from about 56 gai/ha to about 670 gai/ha or to about 224 gai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 4.38 g acid équivalent per hectare (gae/ha) to about 64 gae/ha or about 4.38 gae/ha to about 35 gae/ha. In certain embodiments, the methods utilize the compound of formula (I), or its benzyl ester and clomazone. In one embodiment, the methods utilize the compound of formula (I) and clomazone, wherein the compound of formula (I) is applied at a rate of from about 4.38 g acid équivalent per hectare (gae/ha) to about 64 gae/ha, and clomazone is applied at a rate of about 56 gai/ha to about 670 gai/ha, or (1) is applied at a rate of from about 4.38 g acid équivalent per hectare (gae/ha) to about 64 gae/ha or about 4.38 to about 35 gae/ha, and clomazone is applied at a rate of about 56 gai/ha to about 670 gai/ha or about 56 gai/ha to about 224 gae/ha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and clomazone, wherein the benzyl ester of the compound of formula (I) is applied at a rate of from about 4.38 g acid équivalent per hectare (gae/ha) to about 64 gae/ha, and clomazone is applied at a rate of about 56 gai/ha to about 670 gai/ha or the benzyl ester of the compound of formula (I) and clomazone, wherein the benzyl ester of the compound of formula (1) is applied at a rate of from about 4.38 g acid équivalent per hectare (gae/ha) to about 64 gae/ha, and clomazone is applied at a rate ofabout 56 gai/ha to about 670 gai/ha. In some embodiments, the methods utilize the benzyl ester of the compound of Formula (I) and clomazone, where the benzyl ester of compound of Formula (1) is applied at a rate from about 4.38 gae/ha to about 17.5 gae/ha and clomazone is applied at a rate of about 56 gai/ha to about 224 gai/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or sait or ester thereof in combination with clomazone are used to control CYPD1, CYPRO, DIGSA, ECHCG, ECHCO, IPOHE, LEFCH and SCPMA.

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

The mixtures described herein can be applied in conjunction with one or more other herbicides to control a wider variety of undesirable végétation. When used in conjunction with other herbicides, the composition can be formulated with the other herbicide or herbicides, tank mixed with the other herbicide or herbicides or applied sequentially with the other herbicide or herbicides. Some of the herbicides that can be employed in conjunction with the compositions and methods described herein include, but are not limited to: 4-CPA;

4-CPB; 4-CPP; 2,4-D; 2,4-D choline sait, 2,4-D esters and amines, 2,4-DB; 3,4-DA; 3,4-DB;

2,4-DEB; 2,4-DEP; 3,4-DP; 2,3,6-TBA; 2,4,5-T; 2,4,5-TB; acetochlor, acifluorfen, aclonifen, acrolein, alachlor, allidochlor, alloxydim, allyl alcohol, alorac, ametridione, ametryn, amibuzin, amicarbazone, amidosulfuron, aminocyclopyrachlor, aminopyralîd, amiprofosmethyl, amitrole, ammonium sulfamate, anilofos, anisuron, asulam, atraton, atrazine, azafenidin, azimsulfuron, azîprotryne, barban, BCPC, beflubutamid, benazolin, bencarbazone, benfluralin, benfuresate, bensulfuron-methyl, bensulide, benthiocarb, bentazon-sodium, benzadox, benzfendizone, benzipram, benzobicyclon, benzofenap, benzofluor, benzoylprop, benzthîazuron, bialaphos, bicyclopyrone, bifenox, bilanafos, bispyribac-sodium, borax, bromacil, bromobonil, bromobutide, bromofenoxim, bromoxynil, brompyrazon, butachlor, butafenacil, butamifos, butenachlor, buthidazole, buthiuron, butralin, butroxydim, buturon, butylate, cacodylic acid, cafenstrole, calcium chlorate, calcium cyanamide, cambendichlor, carbasulam, carbetamide, carboxazole chlorprocarb, carfentrazone-ethyl, CDEA, CEPC, chlomethoxyfen, chloramben, chloranocryl, chlorazifop, chlorazine, chlorbromuron, chlorbufam, chloreturon, chlorfenac, chlorfenprop, chlorflurazole, chlorflurenol, chloridazon, chlorimuron, chlomitrofen, chloropon, chlorotoluron, chloroxuron, chloroxynil, chlorpropham, chlorsulfuron, chlorthal, chlorthiamid, cinidon-ethyl, cinmethylin, cinosulfuron, cisanilide, clethodim, clîodinate, 20 clodinafop-propargyl, clofop, clomeprop, cloprop, cloproxydim, clopyralid, cloransulammethyl, CMA, copper sulfate, CPMF, CPPC, credazine, cresol, cumyluron, cyanatryn, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cycluron, cyhalofopbutyl, 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, dîfenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimexano, dimidazon, dinitramine, dinofenate, dinoprop, dinosam, dinoseb, dinoterb, dîphenamid, dipropetryn, diquat, disul, dithiopyr, diuron, DMP A, DNOC, DSMA, EBEP, eglinazine, 30 endothal, epronaz, EPTC, erbon, esprocarb, ethalfluralin, ethbenzamide, ethametsulfuron, ethidimuron, ethiolate, ethobenzamid, etobenzamid, ethofumesate, ethoxyfen, ethoxysulfuron, etinofen, etnipromid, etobenzanid, EXD, fenasulam, fenoprop, fenoxaprop, fenoxaprop-P-ethyl, fenoxaprop-P-ethyl + isoxadifen-ethyl, fenoxasulfone, fenteracol, fenthiaprop, fentrazamide, fenuron, fcrrous sulfate, flamprop, flamprop-M, flazasulfùron, florasulam, fluazifop, fluazifop-P-butyl, fluazolate, flucaAazone, flucetosulfuron, fluchloralin, flufenacet, flufenican, flufenpyr-ethyl, flumetsulàm, flumezin, flumicloracpentyl, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, fluoromidine, fluoronitrofen, fluothiuron, flupoxam, flupropacil, flupropanate, flupyrsulfuron, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fomesafen, foramsulfuron, fosamine, fumiclorac, furyloxyfen, glufosinate, glufosinate-ammonium, glufosinate-P-ammonium, glyphosate salts and esters, halauxifen, halauxifen-methyl, halosafen, halosulfuron-methyl, haloxydine, haloxyfop-methyl, haloxyfop-P-methyl, hexachloroacetone, hexaflurate, hexazinone, imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazosulfuron, imazethapyr, indanofan, indaziflam, iodobonil, iodomethane, iodosulfuron, iodosulfuron-ethyl-sodium, iofensulfuron, ioxynil, ipazine, ipfencarbazone, iprymidam, isocarbamid, isocil, isomethiozin, isonoruron, isopolînate, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, karbutilate, ketospîradox, lactofen, lenacil, linuron, MAA, ΜΑΜΑ, MCPA esters and amines, MCPA-thioethyl, MCPB, mecoprop, mecoprop-P, medinoterb, mefenacet, mefluidide, mesoprazine, mesosulfuron, mesotrione, metam, metamifop, metamitron, metazachlor, metazosulfuron, metflurazon, methabenzthiazuron, methalpropalin, methazole, methiobencarb, methiozolin, methiuron, methometon, methoprotryne, methyl bromide, methyl isothiocyanate, methyldymron, metobenzuron, metobromuron, metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monalide, monisouron, monochloroacetic acid, monolinuron, monuron, morfamquat, MSMA, naproanilide, napropamide, naptalam, neburon, nicosulfuron, nipyraclofen, nitralin, nitrofen, nitrofluorfen, norflurazon, noruron, OCH, orbencarb, or/Ao-dichlorobenzene, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxapyrazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraflufen-ethyl, parafluron, paraquat, pebulate, pelargpnic acid, pendimethalin, penoxsulam, pentachlorophenol, pentanochlor, pentoxazone, perfluidone, pethoxamid, phenisopham, phenmedipham, phenmedipham-ethyl, phenobenzuron, phenylmercury acetate, picloram, picolinafen, pinoxaden, piperophos, potassium arsenite, potassium azide, potassium cyanate, pretilachlor, primisulfuron-methyl, procyazine, prodiamine, profluazol, profluralin, profoxydim, progünazine, prohexadione-calcium, prometon, prometryn, pronamide, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycaibazone, propyrisulfuron, propyzamide, prosulfalin, prosulfocaib, prosulfuron, proxan, prynachlor, pydanon, pyraclonil, pyraflufen-ethyl, pyrasulfotole, pyrazogyl, pyrazolynate, pyrazosulfuron-ethyl, pyrazoxyfen, pyribenzoxim, pyributicarb, pyriclor, pyridafol, pyridate, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithîobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quinonamid, quizalofop, quizalofop-Pethyl, rhodethanil, rimsulfuron, saflufenacil, S-metolachlor, sebuthylazîne, secbumeton, sethoxydim, siduron, simazine, sîmeton, simetryn, SMA, sodium arsenite, sodium azide, sodium chlorate, sulcotrione, sulfallate, sulfentrazone, sulfometuron, sulfosate, sulfosulfuron, sulfuric acid, sulglycapin, swep, SYN-523, TCA, tebutam, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbuchlor, terbumeton, terbuthylazine, terbutryn, tetrafluron, thenylchlor, thiazafluron, thiazopyr, thidiazimin, thidiazuron, thiencarbazone-methyl, thifensulfuron, thifensulfum-methyl, thiobencarb, tiocarbazil, tioclorim, topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, tricamba, triclopyr choline sait, triclopyr esters and amines, tridiphane, trietazîne, trifloxysulfuron, trifluralin, triflusulfuron, trifop, trifopsime, trihydroxytriazine, trimeturon, tripropindan, tritac tritosulfuron, vemolate, xylachlor and salts, esters, optically active isomers and mixtures thereof.

The compositions and methods described herein, can further be used in conjunction with glyphosate, 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, glufosinate, glutamine synthetase inhibitors, dicamba, phenoxy auxins, pyridyloxy auxins, synthetîc 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-hydroxyphcnyl-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 bromoxynîl on glyphosatetolerant, EPSP synthase inhibîtor-tolerant, glufosinate-toierant, glutamine synthetase inhibitor-tolerant, dicamba-tolerant, phenoxy auxîn-tolerant, pyridyloxy auxin-tolerant, auxin-tolerant, auxin transport inhibitor-tolerant, aryloxyphenoxypropionate-tolerant, cyclohexanedione-tolerant, phenylpyrazoline-tolérant, ACCase-tolerant, imîdazolinonetolerant, sulfonylurea-tolerant, pyrimidinylthîobenzoate-tolerant, triazolopyrimidine-tolerant, sulfonylaminocarbonyltriazolinone-tolerant, ALS- or AHAS-to!erant, HPPD-tolerant, phytoene desaturase inhibitor-tolerant, carotenoid biosynthesis inhibitor tolérant, PPOtolerant, 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 inhibitortolerant, triazine-tolerant, bromoxynil-tolerant, and crops possessing multiple or stacked traits conferring tolérance to multiple chemistries and/or multiple modes of action via single and/or multiple résistance mechanisms. In some embodiments, the compound of formula (I) or sait or ester thereof and complementary herbicide or sait or ester thereof are used in combination with herbicides that are sélective for the crop being treated and which complément the spectrum of weeds controlled by these compounds at the application rate employed. In some embodiments, the compositions described herein and other complementary herbicides are applied at the same time, either as a combination formulation or as a tank mix.

In some embodiments, the compositions described herein are employed in combination with one or more herbicide safeners, such as AD-67 (MON 4660), benoxacor, benthiocarb, brassinolide, cloquintocet (mexyl), cyometrinil, daimuron, dichlormid, dicyclonon, dimepiperate, disulfoton, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, fiirilazole, harpin proteins, isoxadifen-ethyl, jiecaowan, jiecaoxi, mefenpyr-diethyl, mephenate, naphthalic anhydride (NA), oxabetrinil, R29148 and /V-phenyl-sulfonylbenzoic acid amides, to enhance their sdectivity. In some embodiments, the safeners are employed in rice, cereal, com, or maize settings. In some embodiments, the safener is cloquintocet or an ester or sait thereof. In certain embodiments, cloquintocet is utilized to antagonize harmfiil 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, ethephon, 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, unîconazole, 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, com, maize, broadleaf crops, oilseed rape/canola, turf, pineapple, sugarcane, sunflower, pastures, grasslands, rangelands, fallowland, tree and vine orchards, plantation crops, vegetables, and non-crop (omamentals) settings. In some embodiments, the plant growth regulator is mixed with the compound of formula (I), or mixed with the compound of formula (I) and clomazone to cause a preferentially advantageous effect on plants.

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

Suitable agricultural adjuvants and carriers include, but are not limited to, crop oi! concentrate; nonylphenol ethoxylate; benzylcocoalkyldimethyl quatemary ammonium sait; blend of petroleum hydrocarbon, alkyl esters, organic acid, and anionic surfactant; Cç-Cn alkylpolyglycoside; phosphated alcohol ethoxylate; natural primary alcohol (Cn-Cie) ethoxylate; di-sec-butylpheno! EO-PO block copolymer, polysiloxane-methyl cap; nonylphenol ethoxylate + urea ammonium nitrate; emulsifîed methylated seed oil; tridecyl alcohol (synthetic) ethoxylate (8EO); tallow amine ethoxylate (15 EO); PEG(400) dioleate99.

Liquid carriers that can be employed include water and organic solvents. The organic solvents include, but are not limited to, petroleum fractions or hydrocarbons such as minerai oil, aromatic solvents, parafiinic oils, and the like; vegetable oils such as soybean oil, rapeseed oil, olive oil, castor oil, sunflower seed oil, coconut oil, com oil, cottonseed oil, linseed oil, palm oil, peanut oil, 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 stéarate, n-butyl oleate, isopropyl myristate, propylene glycol dioleate, di-octyl succinate, di-butyl adipate, di-octyl phthalate and the like; esters ofmono, di and polycarboxylic acids and the like. Spécifie organic solvents include, but are not limited to toluene, xylene, petroleum naphtha, crop oil, acetone, methy! ethyl ketone, cyclohexanone, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol monomethyl ether and diethylene glycol monomethyl ether, methyl alcohol, ethyl alcohol, isopropyl alcohol, amyl alcohol, ethylene glycol, propylene glycol, glycérine, JV-methyl-2-pyrrolidinone, jV, 77-dimethyl alkylamides, di methyl sulfoxide, liquîd fertilizers and the like. In certain embodiments, water is the carrier for the dilution of concentrâtes.

Suitable solid carriers includebut 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, pumicc, wood flour, walnut shell flour, lignin, cellulose, and the like.

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

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

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

In some embodiments, the concentration of the active ingrédients in the compositions described herein is from about 0.0005 to 98 percent by weight. In some embodiments, the concentration is from about 0.0006 to 90 percent by weight. In compositions designed to be employed as concentrâtes, the active ingrédients, in certain embodiments, are présent in a concentration from about 0.1 to 98 weight percent, and in certain embodiment’s about 0.5 to 90 weight percent. Such compositions are, in certain embodiments, diluted with an inert carrier, such as water, before application. The diluted compositions usually applied to weeds or the locus of weeds contain, in certain embodiments, about 0.0006 to 10.0 weight percent active ingrédient and in certain embodiments contain about 0.001 to 6.0 weight percent.

The présent compositions can be applied to undesirable végétation (weeds) or the area adjacent to the weeds 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 daims. Other modifications, uses, or combinations with respect to the compositions described herein will be apparent to a person of ordinary skill in the art without departing from the spirit and scope of the claimed subject matter.

Examples

Results in Examples I and II are greenhouse trial results.

Example I. Evaluation ofPostemergenceFoliar-Applïed Herbicïdal Mixtures forWeed Control in Dîrect-Seeded Rice

Seeds or nutlets of the desired test plant species were planted in a soil matrix prepared by mixîng aloam or sandy loam soil (e.g., 28.6 percent silt, 18.8 percent clay, and 52.6 percent sand, with a pH of abouts.8 and an organic matter content of about 1.8 percent) and calcareous grit in an 80 to 20 ratio. The soil matrix was contained in plastic pots with a volume of 1 quart and a surface area of 83.6 square centimeters (cm²). When required to ensure good germination and healthy plants, a fongicide treatment and/or other chemical or physical treatment was applied. The plants were grown for 8-22 days in a greenhouse with an approximate 14 h photoperiod which was maintained at about 29° C during the day and 26° C during the night. Nutrients (Peters Excel® 15-5-15 5-Ca 2-Mg and iron chelate) were applied in the irrigation solution as needed and water was added on a regular basis. Supplémentai lighting was provided with overhead métal halide 1000-Watt lamps as necessary. The plants were employed for testing when they reached the first through fourth true leaf stage.

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

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

NH₂

Λ .OH ^N 11

O F

Hjcr

Compound A Acid

Compound A Benzyl Ester

Other herbicidal components were applied on an active ingrédient basis and consisted of clomazone formulated as Command® 3ME. Treatment requirements were calculated based upon the rates being tested, the concentration of active ingrédient or acid équivalent in the formulation, and a 12 mL application volume at a rate of 187 L/ha.

For treatments comprised of formulated compounds, measured amounts of compounds were placed individually in 25 mL glass vials and diluted in a volume of 1.25% (v/v) Agri-Dex* crop oil concentrated to obtain 12X stock solutions. If a test compound did not dissolve readily, the mixture was warmed and/or sonicated. Application solutions were prepared by adding an appropriate amount of each stock solution (e.g., 1 mL) and diluted to the appropriate final concentrations with the addition of 10 mL of an aqueous mixture of 1.25% (v/v) crop oil concentrate so that the final spray solutions contained 1.25+/-0.05% (v/v) crop oil concentrate.

For treatments comprised of technical compounds, weighed amounts can be placed individually in 25 mL glass vials and dissolved in a volume of 97:3 v/v acetone/DMSO to obtain 12X stock solutions. If a test compound does not dissolve readily, the mixture can be warmed and/or sonicated. Application solutions can be prepared by adding an appropriate amount of each stock solution (e.g., 1 mL) and diluted to the appropriate final concentrations with the addition of 10 mL of an aqueous mixture of 1.5% (v/v) crop oil concentrate so that the final spray solutions contain 1.25% (v/v) crop oil concentrate. When technical matériels are used, the concentrated stock solutions can be added to the spray solutions so that the final acetone and DMSO concentrations of the application solutions are 16.2% and 0.5%, respectively.

For treatments comprised of formulated and technical compounds, weighed amounts of the technical materials can be placed individually in 25 mL glass vials and dissolved in a volume of 97:3 v/v acetone/DMSO to obtain 12X stock solutions, and measured amounts of the formulated compounds can be placed individually in 25 mL glass vials and diluted in a volume of 1.5% (v/v) crop oil concentrate or water to obtain 12X stock solutions. If a test compound does not dissolve readily, the mixture can be warmed and/or sonicated. Application solutions can be prepared by adding an appropriate amount of each stock solution (e.g., I mL) and diluted to the appropriate final concentrations with the addition of an appropriate amount of an aqueous mixture of 1.5% (v/v) crop oil concentrate so that the final spray solutions contain 1.25% (v/v) crop oil concentrate. As required, additional water and/or 97:3 v/v acetone/DMSO can be added to individual application solutions so that the final acetone and DMSO concentrations of the application solutions being compared are 8.1% and 0.25%, respectively.

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

The treated plants and control plants were placed in a greenhouse as described above and watered by sub-ïrrigation to prevent wash-offof the test compounds. After approximately 3 weeks, the condition of the test plants as compared with that of the untreated plants was determîned visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury or growth inhibition and 100 corresponds to complété kill.

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

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

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

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

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

The compounds tested, application rates employed, plant species tested, and results are given in Tables 1-2.

Table 1. Synergistic Activity of Foliar-Applied Compound A Acid and Clomazone Herbicidal Compositions on Weed Control in a Rice Cropping System.

Compound A Acid	Clomazone	Visual Weed Control (%) -19 DAA
		DIGSA
gae/ha	gai/ha	Obs	Exp
4.38	0	30	-
0	56	0	-
0	112	0	-
0	224	0	-
4.38	56	45	30
4.38	112	40	30
4.38	224	45	30

Compound A Acid	Clomazone	Visual Weed Control (%)-19 DAA
		LEFCH
gae/ha	gai/ha	Obs	Exp
17.5	0	55	-
0	56	0	-
0	112	0	-
0	224	15	-
17.5	56	55	55
17.5	112	70	55
17.5	224	80	62

Compound A Acid	Clomazone	Visual Weed Control (%) -19 DAA
		IPOHE
gae/ha	gai/ha	Obs	Exp
4.38	0	0	•
8.75	0	10	-
0	112	20	-
0	224	20	-
4.38	112	15	20
8.75	112	60	28
4.38	224	60	20
8.75	224	50	28

Table 2. Synergistic Activity of Folîar-Applied Compound A Benzyl Ester and Clomazone Herbicidal Compositions on Weed Control in a Rîce Croppîng System.

Compound A Benzyl Ester	Clomazone	Visual Weed Control (%)-19 DAA
		ECHCG
gae/ha	gai/ha	Obs	Exp
4.38	0	55	-
0	56	10	-
0	112	10	-
0	224	10	-
4.38	56	85	60
4.38	112	80	60
4.38	224	75	60

Compound A Benzyl Ester	Clomazone	Visual Weed Control (%) -19 DAA
		ECHCO
gae/ha	gai/ha	Obs	Exp
4.38	0	65	-
0	56	10	-
0	112	10	-
0	224	10	-
4.38	56	70	69
4.38	112	90	69
4.38	224	90	69

Compound A Benzyl Ester	Clomazone	Visual Weed Control (%) -19 DAA
		LEFCH
gae/ha	gai/ha	Obs	Exp
17.5	0	30	-
0	56	0	-
0	112	0	-
0	224	15	-
17.5	56	45	30
17.5	112	55	30
17.5	224	75	41

ιο

D1GSA Dîgitaria sanguinalis (L.) Scop.; crabgrass, large

ECHCG Echinochloa crus-gallî (L.) Beauv.; bamyardgrass

ECHCO Echinochloa colona (L.) Link; junglerice

IPOHE Ipomoea hederacea Jacq.; momingglory, ivyleaf

LEFCH Leptochloa chinensis (L.) Nees; sprangletop, Chinese gae/ha = grains acid équivalent per hectare gai/ha = grams active ingrédient per hectare

Obs = observed value

Exp = expected value as calculated by Colby’s équation

DAA — days after application

Example II. Evaluation of In-Water Applied Herbicidal Mixtures for Weed Control in Transplanted Paddy Rice

Weed seeds or nutlets of the desired test plant species were planted in puddled soil (mud) prepared by mixing a shredded, non-sterilized minerai soil (50.5 percent silt, 25.5 percent clay, and 24 percent sand, with a pH of about 7.6 and an organic matter content of about 2.9 percent) and water at a 1:1 volumétrie ratio. The prepared mud was dîspensed in 365 mL aliquots into 16-ounce (oz.) non-perforated plastic pots with a surface area of 86.59 square centîmeters (cm²) leaving a headspace of 3 centimeters (cm) in each pot. Rice seeds were planted in Sun Gro MetroMix® 306 planting mixture, which typically has a pH of 6.0 to

6.8 and an organic matter content of about 30 percent, in plastic plug trays. Seedlings at the second or third leaf stage of growth were transplanted into 860 mL of mud contaîned in 32oz. non-perforated plastic pots with a surface area of 86.59 cm² 4 days prior to herbicide application. The paddy was created by filling the headspace of the pots with 2.5 to 3 cm of water. When required to ensure good germination and healthy plants, a fongicide treatment and/or other chemical or physical treatment was applied. The plants were grown for 4-22 days in a greenhouse with an approximate 14 h photoperiod which was maintained at about 29*C during the day and about 26°C during the nîght. Nutrients were added as Osmocote® (17:6:10, N:P:K + minor nutrients) at 2 g per 16-oz. pot and 4 g per 32-oz. pot. Water was added on a regular basis to maintain the paddy flood, and supplémentai lighting was provided with overhead métal halide 1000-Watt lamps as necessary. The plants were employed for testing when they reached the first through fourth true leaf stage.

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

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

Compound A Acid

Compound A Benzyl Ester Other herbicidal components were applied on an active ingrédient basis and consisted of clomazone formulated as Command® 3ME

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

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

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

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

The treated plants and control plants were placed in a greenhouse as described above and water was added as needed to maintaîn a paddy flood. After approximately 3 weeks the condition of the test plants as compared with that of the untreated plants was determined visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury or growth inhibition and 100 corresponds to complété kill.

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

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

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

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

B = observed efïïcacy of active ingrédient B at the same concentration as used in the 10 mixture.

Some of the compounds tested, application rates employed, plant species tested, and résulte are given in Tables 3-4.

Table 3. Synergistic Activity of In-Water Applications of Compound A Acid and Clomazone Herbicidal Compositions on Weed Control in a Rice Cropping System.

Compound A Acid	Clomazone	Visual Weed Control (%) - 21 DAA
		CYPRO
gae/ha	gai/ha	Obs	Exp
8.75	0	0	-
17.5	0	30	-
35	0	85	-
0	112	0	-
8.75	112	30	0
17.5	112	30	30
35	112	100	85

Compound A Acid	Clomazone	Visual Weed Control (%) - 21 DAA
		CYPDI
gae/ha	gai/ha	Obs	Exp
16	0	30	-
0	224	20	-
0	448	40	-
16	224	85	44
16	448	100	58

Compound A Acid	Clomazone	Visual Weed Control (%)-22 DAA
		SCPMA
gae/ha	gai/ha	Obs	Exp
16	0	0	-
32	0	0	-
64	0	30	-
0	448	25	-
16	448	20	25
32	448	50	25
64	448	60	48

Table 4. Synergistic Activity of In-Water Applications of Compound A Benzyl Ester and Clomazone Herbicidal Compositions on Weed Control in a Rice Cropping System.

Compound A Benzyl Ester	Clomazone	Visual Weed Control (%) - 21 DAA
		SCPMA
gae/ha	gai/ha	Obs	Exp
4.38	0	0
8.75	0	0
17.5	0	0
0	112	0
4.38	112	20	0
8.75	112	20	0
17.5	112	100	0

Compound A Benzyl Ester	Clomazone	Visual Weed Control (%) - 21 DAA
		CYPRO
gae/ha	gai/ha	Obs	Exp
8	0	70	-
16	0	95	-
32	0	90	-
0	448	0	-
8	448	95	70
16	448	100	95
32	448	100	90

Compound A Benzyl

Clomazone

Visual Weed Control (%)- 19

Ester		DAA
		SCPMA
gae/ha	gai/ha	Obs	Exp
8	0	0	-
16	0	0	-
32	0	0	-
0	670	0	-
8	670	10	0
16	670	10	0
32	670	90	0

CYPDI Cypertis difformis L.

CYPRO Cyperus rotundus L.

SCPMA Bolboschoenus maritimiis (L.) Palla gae/ha ® grams acid équivalent per hectare gai/ha = grams active ingrédient per hectare Obs = observed value

Exp = expected value as calculated by Colby’s équation DAA - days after application sedge, smallflower umbrella nutsedge, purple clubrush, sea

Claims (11)

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

   H,C'° O or an agriculturally acceptable sait or ester thereof and (b) clomazone or an agriculturally acceptable sait, carboxylic acid, carboxylate sait, or ester thereof.
2. 2. The composition of claim 1, wherein (a) is the compound of formula (I), a Cm alkyl ester of the compound of formula (1), or a benzyl ester of the compound of formula (I).
3. 3. The composition of any of daims 1-2, further comprising an agriculturally acceptable adjuvant or carrier.
4. 4. The composition of any of daims 1 -3, further comprising a herbicide safener.
5. 5. A method of controlling undesirable végétation which comprises contacting the végétation or the locus thereof with or applying to the soil or water to prevent the emergence or growth of végétation a herbicidally effective amount of (a) a compound of the formula (I) _H]c'° ω or an agriculturally acceptable sait or ester thereof and (b) clomazone or an agriculturally acceptable sait, carboxylic acid, carboxylate sait, or ester thereof.
6. 6. The method of claim 5, wherein (a) is the compound of formula (I), a Cm alkyl ester of the compound of formula (I), or a benzyl ester of the compound of formula (I).
7. 7. The method of any of daims 5-6, wherein the undesirable végétation is controlled in direct-seeded, water-seeded and transplanted rice, cereals, wheat, barley, oats, rye, sorghum, com/maize, sugarcane, sunflower, oilseed râpe, canota, sugar beet, soybean, cotton, pineapple, pastures, grasslands, rangelands, fallowland, turf, tree and vine orchards, aquatîcs, industrial végétation management (IVM) or rights of way (ROW).
8. 8. The method of any of claîms 5-7, wherein the (a) and (b) are applied pre-emergently to the weed or the crop.
9. 9. The method of any of daims 5-8, wherein the undesirable végétation is controlled in glyphosate-, 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitor-, glufosinate-, glutamine synthetase inhibitor-, dicamba-, phenoxy auxin-, pyridyloxy auxin-, synthetic auxin-, auxin transport inhibitor-, aryloxyphenoxypropionate-, cyclohexanedione-, phenylpyrazoline-, acetyl CoA carboxylase (ACCase) inhibitor-, imidazolinone-, sulfonylurea-, pyrimidinylthiobenzoate-, triazolopyrimidine-, sulfonylaminocarbonyltriazolinone-, acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors-, 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor-, phytoene desaturase inhibitor-, carotenoid biosynthesis inhibitor-, protoporphyrinogen oxidase (PPO) inhibitor-, cellulose biosynthesis inhibitor-, mitosis inhibitor-, microtubule inhibitor-, very long chain fatty acid inhibitor-, fatty acid and lipid biosynthesis inhibitor-, photosystem 1 inhibitor-, photosystem 11 inhibitor-, triazine-, or bromoxynil- tolérant crops.
10. 10. The method of claim 9, wherein the tolérant crop possesses multiple or stacked traits conferring tolérance to multiple herbicides or multiple modes of action.
11. 11. The method of daims 5-10, wherein the undesirable végétation comprises a herbicide résistant or tolérant weed.