OA17280A - Herbicidal compositions comprising 4-amino3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxylphenyl) pyridine-2-carboxylic acid or a derivative thereof and certain PS II inhibitors. - Google Patents

Herbicidal compositions comprising 4-amino3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxylphenyl) pyridine-2-carboxylic acid or a derivative thereof and certain PS II inhibitors. Download PDF

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Publication number
OA17280A
OA17280A OA1201500032 OA17280A OA 17280 A OA17280 A OA 17280A OA 1201500032 OA1201500032 OA 1201500032 OA 17280 A OA17280 A OA 17280A
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OA
OAPI
Prior art keywords
compound
sait
formula
ester
inhibitor
Prior art date
Application number
OA1201500032
Inventor
Clara YERKES
Richard Mann
Paul Schmitzer
Norbert Satchivi
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Dow Agrosciences Llc
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Publication of OA17280A publication Critical patent/OA17280A/en

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Abstract

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

Description

Provided herein are herbicidal compositions comprising and methods for controlling undesirable végétation utilizing (a) 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3methoxyphenyl)pyridine-2-carboxylic acid or an agriculturally acceptable ester or sait thereof and (b) a photosystem (PS) II inhibitor selected from the group consisting of: atrazine, bentazonsodium, bromoxynil, chlorotoluron, cyanazine, diuron, hexazinone, ioxynil, isoproturon, linuron, methibenzuron, metribuzin, propanil, pyridate, siduron, simazine, simetryne, tebuthiuron and terbuthylazine, or dérivative, e.g., sait or ester thereof.
Background
The protection of crops from weeds and other végétation which inhibit crop growth is a constantly recurring problem in agriculture. To help combat this problem, researchers in the field of synthetic chemistry hâve produced an extensive variety of chemicals and chemical formulations effective in the control of such unwanted growth. Chemical herbicides of many types hâve been disclosed in the literature and a large number are in commercial use. However, there remains a need for compositions and methods that are effective in controlling undesirable végétation.
Summarv
Several embodiments are recited below. In the embodiments, the ratio of compound (a) to compound (b) can be expressed in units 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 synergistic herbicidal composition comprising a herbicidally effective amount of (a) a compound of the formula (I)
OH (I) or an agriculturally acceptable sait or ester thereof and (b) atrazine, bentazon, bentazon-sodium, bromoxynil, chlorotoluron, cyanazine, diuron, hexazinone, ioxynil, isoproturon, linuron, methibenzuron, metribuzin, propanil, pyridate, siduron, simazine, simetryne, tebuthiuron or terbuthylazine or agriculturally acceptable sait or ester thereof.
A second embodiment includes the mixture of the first embodiment in winch (a) is a Cm alkyl or benzyl ester of compound (I).
I
A third embodiment includes the mixture of the first embodiment in which (a) is a Cm alkyl ester of compound (I).
A fourth embodiment includes the mixture of the second embodiment in which (a) is a benzyl ester of compound (I). !
A fifth embodiment includes the mixture of the first embodiment in which (a) is the compound of formula (I), which is the carboxylic acid.
A sixth embodiment includes the mixture of the first embodiment in which (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is atrazine.
A seventh embodiment includes the mixture of the first embodiment in which (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is bentazon or bentazon-sodium.
An eighth embodiment includes the mixture of the first embodiment in which (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is bromoxynil or bromoxynil octanoate.
A ninth embodiment includes the mixture of the first embodiment in which (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is chlorotoluron.
A tenth embodiment includes the mixture of the first embodiment in which (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is cyanazine.
An eleventh embodiment includes the mixture of the first embodiment in which (a) is the
I compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is diuron.
A twelfth embodiment includes the mixture of the first embodiment in which (a) is the i
compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is hexazinone.
-3A thirteenth embodiment includes the mixture of the first embodiment in which (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is ioxynil.
A fourteenth embodiment includes the mixture of the first embodiment in which (a) is the
I compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is isoproturon.
A fifteenth embodiment includes the mixture of the first embodiment in which (a) is the
I compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is linuron.
A sixteenth embodiment includes the mixture of the first embodiment in which (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is methibenzuron.
I
A seventeenth embodiment includes the mixture of the first embodiment in which (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is metribuzin.
An eighteenth embodiment includes the mixture of the first embodiment in which (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is propanil.
A nineteenth embodiment includes the mixture of the first embodiment in which (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is pyridate.
A twentieth embodiment includes the mixture of the first embodiment in which (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is siduron.
A twenty-first embodiment includes the mixture of the first embodiment in which (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is simazine.
A twenty-second embodiment includes the mixture of the first embodiment in which (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is simetryne.
A twenty-third embodiment includes the mixture ofthe first embodiment in which (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is tebuthiuron.
A twenty-fourth embodiment includes the mixture of the first embodiment in which (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is terbuthylazine.
A twenty-fifth embodiment includes the mixture of any of the first through twenty-fourth embodiments, further comprising an herbicide safener.
A twenty-sixth embodiment includes the mixture of the second embodiment in which the weight ratio of compound of formula (I) or agriculturally acceptable sait or ester thereof to atrazine or agriculturally acceptable sait thereof is selected from the group of ranges of ratios and ratios consisting of: about 1:2240 to about 6:1, about 1:1120 to about 3:1, about 1:256 to
I about 1:16, about 6:1, about 1:7, about 1:9, about 1:16, about 1:17.5, about 1:32, about 1:35, about 1:64, about 1:70, about 1:128, about 1:140, about 1:256, and about 1:2240, or within any range defined between any pair of the foregoing values. !
-4A twenty-seventh embodiment includes the mixture of the second embodiment in which the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to bentazon, bentazon-sodium, or agriculturally acceptable sait thereof is selected from the group of ranges of ratios and ratios consisting of: about 1:1120 to about 3:1, about 1:560 to about 2:1, about 1:256 to about 1.4:1, about 1:96 to about 1:3.4, about 3:1, about 1:3.4, about 1:6, about 1:7, about 1:12, about 1:14, about 1:16, about 1:20, about 1:24, about 1:26, about 1:32, about 1:40, about 1:48, about 1:52.5, about 1:96, about 1:256, and about 1:1120, or within any range defined between any pair of the foregoing values.
A twenty-eighth embodiment includes the mixture of the second embodiment in which the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to bromoxynil or agriculturally acceptable sait or ester thereof is selected from the group of ranges of ratios and ratios consisting of: from about 1:280 to about 12:1, about 1:140 to about 6:1, about 1:70 to about 3:1, about 1:35 to about 2:1, about 1:17.5 to about 1:1, about 12:1, about 1:1, about 1:2, about 1:4, about 1:4.4, about 1:8, about 1:12.5, about 1:17.5, and about 1:280, or within any range defined between any pair of the foregoing values.
A twenty-ninth embodiment includes the mixture of the second embodiment in which the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to chlorotoluron or agriculturally acceptable sait or ester thereof is from about 1:1750 to about 1.5:1.
A thirtieth embodiment includes the mixture of the second embodiment in which the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to cyanazine or agriculturally acceptable sait thereof is selected from the group of ranges of ratios and ratios consisting of: about 1:2650 to about 6:1, about 1:1325 to about 3:1, about 1:662 to about 2:1, about 1:110 to about 1:5.3, about 6:1, about 1:5.3, about 1:8.6, about 1:13.8, about 1:17.2, about 1:25, about 1:27.5, about 1:34.4, about 1:110, about 1:662, about 1:1325, and about 1:2650, or within any range defined between any pair of the foregoing values.
A thirty-first embodiment includes the mixture of the second embodiment in which the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to diuron or agriculturally acceptable sait thereof is selected from the group of ranges of ratios and ratios consisting of: about 1:3600 to about 6:1, about 1:1800 to about 3:1, about 1:900 to about 1:2, about 1:70 to about 1:9, about 6:1, about 1:9, about 1:17.5, about 1:35, about 1:70, about 1:900, about 1:1800, and about 1:3600, or within any range defined between any pair of the foregoing values.
-5A thirty-second embodiment includes the mixture of the second embodiment in which the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to hexazinone or agriculturally acceptable sait thereof is selected from the group of ranges of ratios and ratios consisting of: about 1:2500 to about 12:1, about 1:1250 to about 2:1, about 1:625 to about 1:1, about 1:156 to about 1:20, about 12:1, about 1:20, about 1:39, about 1:78, about 1:156, and about 1:2500, or within any range defined between any pair of the foregoing values.
A thirty-third embodiment includes the mixture of the second embodiment in which the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to ioxynil or agriculturally acceptable sait or ester thereof is selected from the group of ranges of ratios and ratios consisting of: about 1:200 to about 12:1, about 1:100 to about 1:1, about 1:37.5 to about 1:9, about 12:1, about 1:9.4, about 1:19, about 1:37.5, and about 1:200, or within any range defined between any pair of the foregoing values.
A thirty-fourth embodiment includes the mixture of the second embodiment in which the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to isoproturon or agriculturally acceptable sait thereof is selected from the group of ranges of ratios and ratios consisting of: about 1:750 to about 12:1, about 1:375 to about 6:1, about 1:600 to about 1:37.5, about 1:300 to about 1:75, about 1:750, about 1:600, about 1:375, about 1:300, about 1:150, about 1:75, about 1:37.5, about 1:1, about 6:1, and about 12:1.
A thirty-fifth embodiment includes the mixture of the second embodiment in which the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to linuron or agriculturally acceptable sait thereof is selected from the group of ranges of ratios and ratios consisting of: from about 1:2250 to about 6:1, about 1:1125 to about 3:1, about 1:562 to about 1:1, about 1:39 to about 1:19, about 6:1, about 3:1, about 1:19.4, about 1:38.8, about 1:562, about 1:1125, and about 1:2250, or within any range defined between any pair of the foregoing values.
A thirty-sixth embodiment includes the mixture of the second embodiment in which the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to methibenzuron or agriculturally acceptable sait thereof is selected from the group of ranges of ratios and ratios consisting of: about 1:1400 to about 4:1, about 1:700 to about 2:1, and about 1:350 to about 1:1.
A thirty-seventh embodiment includes the mixture of the second embodiment in which the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to metribuzin or agriculturally acceptable sait thereof is selected from the group of ranges of
-6ratios and ratios consisting of: about 1:2800 to about 6:1, about 1:1400 to about 3:1, about 1:700 to about 2:1, about 1:168 to about 1.3:1, about 1:26 to about 1:5, about 6:1, about 3:1, about 2:1, about 1:3, about 1:5, about 1:6.7, about 1:10, about 1:13, about 1:20, about 1:26, about 1:168, about 1:700, about 1:1400, and about 1:2800, or within any range defined between any pair of the foregoing values.
A thirty-eighth embodiment includes the mixture of the second embodiment in which the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to propanil or agriculturally acceptable sait thereof is selected from the group of ranges of ratios and ratios consisting of: about 1:2800 to about 1:1, about 1:1400 to about 1:4, about 1:767 to about 1:24, about 1:767 to about 1:12, about 1:384 to about 1:48, about 1:1, about 1:4, about 1:12, about 1:24, about 1:48, about 1:96, about 1:173, about 1:192, about 1:210, about 1:384, about 1:560, about 1:767, about 1:1400, and about 1:2800, or within any range defined between any pair of the foregoing values.
A thirty-ninth embodiment includes the mixture of the second embodiment in which the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to pyridate or agriculturally acceptable sait thereof is selected from the group of ranges of ratios and ratios consisting of: about 1:800 to about 12:1, about 1:800 to about 6:1, about 1:800 to about 3:1, about 1:800 to about 1:1, about 1:400 to about 6:1, about 1:400 to about 3:1, about 1:400 to about 1:1,and about 1:200 to about 1:16.
A fortieth embodiment includes the mixture of the second embodiment in which the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to siduron or agriculturally acceptable sait thereof is from selected from the group of ranges of ratios and ratios consisting of: about 1:4500 to about 2:1, about 1:2250 to about 1:1, about 1:1125 to about 1:5: and about 1:625 to about 1:50.
A forty-first embodiment includes the mixture of the second embodiment in which the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to simazine or agriculturally acceptable sait thereof is selected from the group of ranges of ratios and ratios consisting of: about 1:4250 to about 2:1, about 1:2125 to about 1:1, about 1:560 to about 1:8, about 1:280 to about 1:17.5, about 1:140 to about 1:17.5, about 2:1, about 1:8, about 1;17.5, about 1:35, about 1:70, about 1:140, about 1:280, about 1:560, about 1:2125, and about 1:4250, or within any range defined between any pair of the foregoing values.
A forty-second embodiment includes the mixture of the second embodiment in which the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to simetryne or agriculturally acceptable sait thereof is selected from the group of ranges of ratios
-7and ratios consisting of: about 1:1000 to about 12:1, about 1:500 to about 6:1, about 1:250 to about 1:1, about 1:56 to about 1:3.5, about 12:1, about 6:1, about 1.3.5, about 1:1, about 1:7, about 1:14, about 1:28, about 1:56, about 1:250, about 1:500, and about 1:1000, or within any range defîned between any pair of the foregoing values.
A forty-third embodiment includes the mixture of the second embodiment in which the weight ratio of the compound of formula (I) or âgriculturally acceptable sait or ester thereof to tebuthiuron or âgriculturally acceptable sait thereof is selected from the group of ranges of ratios and ratios consisting of: about 1:2240 to about 2:1, about 1:1120 to about 1:1, about 1:840 to about 1:6, about 1:210 to about 1:6, about 2:1, about 1:1, about 1:2, about 1:3, about 1:6, about 1:9, about 1:13, about 1:17.5, about 1:26, about 1:35, about 1:52.5, about 1:70, about 1:105, about 1:140, abouti :210, about 1:840, and about 1:2240, or within any range defîned between any pair of the foregoing values.
A forty-fourth embodiment includes the mixture of the second embodiment in which the weight ratio of the compound of formula (I) or âgriculturally acceptable sait or ester thereof to terbuthylazine or âgriculturally acceptable thereof is selected from the group of ranges of ratios and ratios consisting of: about 1:1500 to about 2.4:1, about 1:750 to about 1:1, about 1:375 to about 1:3, about 1:200 to about 1:10, about 1:62.5 to about 1:31, about 2.4:1, about 1:31.3, about 1:62.5, and about 1:1500, or within any range defîned between any pair of the foregoing values.
A forty-fifth embodiment includes the mixture of any of the first though forty-fourth embodiments father comprising an âgriculturally acceptable adjuvant or carrier.
A forty-sixth embodiments includes the mixture of any of the first though forty-fourth embodiments which is synergistic as determined by the Colby équation.
A forty-seventh embodiment includes 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 the composition of any of first to fortysixth embodiments.
A forty-eighth embodiment includes 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)
-8NH2
Cl
OH or an agriculturally acceptable sait or ester thereof and (b) atrazine, bentazon, bentazon-sodium, bromoxynil, chlorotoluron, cyanazine, diuron, hexazinone, ioxynil, isoproturon, linuron, methibenzuron, metribuzin, propanil, pyridate, siduron, simazine, simetryne, tebuthiuron or terbuthylazine or agriculturally acceptable sait or ester thereof.
A forty-ninth embodiment includes the method of the forty-seventh or forty-eighth embodiment, wherein the method is practiced in at least one member of the group consisting of direct-seeded, water-seeded and transplanted rice, cereals, wheat, barley, oats, rye, sorghum, com/maize, sugarcane, sunflower, oilseed râpe, canola, sugar beet, soybean, cotton, pineapple, pastures, grasslands, rangelands, fallowland, turf, tree and vine orchards, aquatics, industrial végétation management (IVM) or rights of way (ROW).
A fiftieth embodiment includes the method of the forty seventh embodiment or fortyeighth embodiment, wherein the undesirable végétation is immature.
A fifty-first embodiment includes the method of the forty-seventh or forty-eighth embodiment, wherein the (a) and (b) are applied to water.
A fifty-second embodiment includes the method of the fifty-first embodiment, wherein the water is part of a flooded rice paddy.
A fifty-third embodiment includes the method of the forty-seventh or forty-eighth embodiment, wherein the (a) and (b) are applied pre-emergently to the weed or the crop.
A fifty-fourth embodiment includes the method of forty-seventh or forty eighth embodiment, wherein the (a) and (b) are applied post-emergently to the weed or the crop.
A fifty-fifth embodiment includes the method of forty-seventh or forty-eighth embodiment, wherein the undesirable végétation is controlled in glyphosate-, 5enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitor-, glufosinate-, glutamine synthetase inhibitor-, dicamba-, phenoxy auxin-, pyridyloxy auxin-, synthetic auxin-, auxin transport inhibitor-, aryloxyphenoxypropionate-, cyclohexanedione-, phenylpyrazoline-, acetyl CoA carboxylase (ACCase) inhibitor-, imidazolinone-, sulfonylurea-, pyrimidinylthiobenzoate-, triazolopyrimidine-, sulfonylaminocarbonyltriazolinone-, acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors-, 4-hydroxyphenyl-pyruvate dioxygenase
-9(HPPD) inhibitor-, phytoene desaturase inhibitor-, carotenoid biosynthesis inhibitor-, protoporphyrinogen oxidase (PPO) inhibitor-, cellulose biosynthesis inhibitor-, mitosis inhibitor, microtubule inhibitor-, very long chain fatty acid inhibitor-, fatty acid and lipid biosynthesis inhibitor-, photosystem I inhibitor-, photosystem II inhibitor-, triazine-, or bromoxynil- tolérant crops.
A fifty-sixth embodiment includes the method of the fifty fifth embodiment, wherein the tolérant crop possesses multiple or stacked traits conferring résistance or tolérance to multiple herbicides or multiple modes of action.
A fifty-seventh embodiment includes the method of the forty-seventh or forty-eighth embodiment, wherein the undesirable végétation comprises a herbicide résistant or tolérant weed.
A fifty-eighth embodiment includes the method of the fifty-seventh embodiment, wherein the résistant or tolérant weed is a biotype with résistance or tolérance to multiple herbicides, multiple chemical classes, multiple herbicide modes-of-action or via multiple résistance mechanisms.
A fifty-ninth embodiment includes the method of the fifty-seventh embodiment, wherein the résistant or tolérant weed is a biotype résistant or tolérant to acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors, photosystem II inhibitors, acetyl CoA carboxylase (ACCase) inhibitors, synthetic auxins, auxin transport inhibitors, photosystem I inhibitors, 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, microtubule assembly inhibitors, fatty acid and lipid synthesis inhibitors, protoporphyrinogen oxidase (PPO) inhibitors, carotenoid biosynthesis inhibitors, very long chain fatty acid (VLCFA) inhibitors, phytoene desaturase (PDS) inhibitors, glutamine synthetase inhibitors, 4-hydroxyphenylpyruvate-dioxygenase (HPPD) inhibitors, mitosis inhibitors, cellulose biosynthesis inhibitors, herbicides with multiple modes-of-action, quinclorac, arylaminopropionic acids, difenzoquat, endothall, or organoarsenicals.
A sixtieth embodiment includes the method of controlling undesirable végétation including the step of applying a herbicidally effective amount of at least one mixture according to the twenty-sixth embodiment wherein the amount of the mixture is applied at a rate, expressed in gai/ha or gae/ha of atrazine selected from the group of rates and ranges of rates consisting of, about: 50,140,280, 560,1120,2240, and 4400 or within any range defined between any pair of the foregoing values.
-10A sixty-first embodiment includes the methods according to either of the twenty-sixth or sixtieth embodiments wherein the controlled plant is at least one plant selected from the group consisting of: BRAPP, CYPIR, ECHCG, ECHCO, and XANST, still other embodiments include controlling plants from the généra consisting of: Brachiaria or Urochloa, Echinochloa, Bolboschoenus, and Xanthium.
A sixty-second embodiment includes the method of controlling undesirable végétation comprising the step of applying a herbicidally effective amount of at least one mixture according to the twenty-seventh embodiment wherein the amount of the mixture is applied at a rate, expressed in gai/ha or gae/ha of bentazon or bentazon-sodium selected from the group of rates and ranges of rates consisting of, about: 60,105,120,210,420, 840,1120, and 2240, or within any range defined between any pair of the foregoing values.
A sixty-third embodiment includes the methods according to either ofthe twenty-seventh or sixty-second embodiments wherein the controlled plant is at least one plant selected from the group consisting of: BRSNW, COMBE, ECHCG, ECHOR, IPOHE, LEFCH, SCPMA, and SETFA, still other embodiments include controlling plants from the généra consisting of: Brassica, Commelina, Echinochloa, Ipomoea, Leptochloa, Bolboschoenus or Schoenoplectus, and Xanthium.
A sixty-fouth embodiment includes the methods of controlling undesirable végétation comprising the step of applying a herbicidally effective amount of at least one mixture according to the twenty-eighth embodiment wherein the amount of the mixture is applied at a rate, expressed in gai/ha or gae/ha of bromoxynil selected from the group of rates and ranges of rates consisting of, about: 25, 35,70,140,280, or 560 within any range defined between any pair of the foregoing values.
A sixty-fifth embodiment includes the methods according to either of the twenty-eighth or sixty-fourth embodiments wherein the controlled plant is at least one plant selected from the
-11 group consisting of: AMARE, ECHCG, IPOHE, and SETFA, still other embodiments include controliing plants from the généra consisting of: Amaranthus, Echinochloa, Ipomoea, and Setaria.
A sixty-sixth embodiment includes the methods of controliing undesirable végétation comprising the step of applying a herbicidally effective amount of at least one mixture according to the twenty-ninth embodiment wherein the amount of the mixture is applied at a rate, expressed in gai/ha or gae/ha of chlorotoluron seiected from the group of rates and ranges of rates consisting of, about: 200,400, 800,1600, or 3500 within any range defined between any pair of the foregoing values.
A sixty-seventh embodiment includes the methods of controliing undesirable végétation comprising the step of applying a herbicidally effective amount of at least one mixture according to the thirtieth embodiment wherein the amount of the mixture is applied at a rate, expressed in gai/ha or gae/ha of cyanazine seiected from the group of rates and ranges of rates consisting of, about: 50,170,275,440, 880,1325,2650, or 5300 within any range defined between any pair of the foregoing values.
A sixty-eighth embodiment includes the methods according to either of the thirtieth or sixty-seventh embodiments wherein the controlled plant is at least one plant seiected from the group consisting of: BRAPP and IPOHE, still other embodiments include controliing plants from the généra consisting of: Brachiaria or Urochloa and Ipomoea.
A sixty-ninth embodiment includes the methods of controliing undesirable végétation comprising the step of applying a herbicidally effective amount of at least one mixture according to the thirty-first embodiment wherein the amount of the mixture is applied at a rate, expressed in gai/ha or gae/ha of diuron seiected from the group of rates and ranges of rates consisting of, about: 50,100,140,280, 560,1120,2240,4480, or 7200 within any range defined between any pair of the foregoing values.
-12A seventieth embodiment includes the methods according to either of the thirty-first or sixty-ninth embodiments wherein the controlled plant is at least one plant selected from the group consisting of: ABUTH, BRAPP, ECHCG, ECHCO, SETFA, and SETVI, still other embodiments include controlling plants from the généra consisting of: Abutilon, Brachiaria or Urochloa, Echinochloa, and Setaria.
A seventy-first embodiment includes the methods of controlling undesirable végétation comprising the step of applying a herbicidally effective amount of at least one mixture according to the thirty-second embodiment wherein the amount of the mixture is applied at a rate, expressed in gai/ha or gae/ha of hexazinone selected from the group of rates and ranges of rates consisting of, about: 25, 50,100,200,400,625,1250,2500, or 5000 within any range defined between any pair of the foregoing values.
A seventy-second embodiment includes the methods according to either of the thirtysecond or seventy-first embodiments wherein the controlled plant is at least one plant selected from the group consisting of: ECHCG, ECHCO, and IPOHE, still other embodiments include controlling plants from the généra consisting of: Echinochloa and Ipomoea.
A seventy-third embodiment includes the methods of controlling undesirable végétation comprising the step of applying a herbicidally effective amount of at least one mixture according to the thirty-third embodiment wherein the amount of the mixture is applied at a rate, expressed in gai/ha or gae/ha of ioxynil selected from the group of rates and ranges of rates consisting of, about: 25, 50,100,200,300, or 400 within any range defined between any pair of the foregoing values.
A seventy-forth embodiment includes the methods according to either of the thirty-third or seventy-third embodiments wherein the controlled plant is at least one plant selected from the group consisting of: IPOHE, still other embodiments include controlling plants from the généra consisting of: Ipomoea.
-13A seventy-fifth embodiment includes the methods of controlling undesirable végétation comprising the step of applying a herbicidally effective amount of at least one mixture according to the thirty-fourth embodiment wherein the amount of the mixture is applied at a rate, expressed in gai/ha or gae/ha of isoproturon selected from the group of rates and ranges of rates consisting of, about: 25,50,100,200,400, 800, or 1500 within any range defined between any pair of the foregoing values.
A seventy-sixth embodiment includes the methods of controlling undesirable végétation comprising the step of applying a herbicidally effective amount of at least one mixture according to the thirty-fifth embodiment wherein the amount of the mixture is applied at a rate, expressed in gai/ha or gae/ha of linuron selected from the group of rates and ranges of rates consisting of, about: 50,100,200,400,620,1125,2250, or 4500 within any range defined between any pair ofthe foregoing values.
A seventy-seventh embodiment includes the methods according to either of the thirtyfifth or seventy-sixth embodiments wherein the controlled plant is at least one plant selected from the group consisting of: BRAPP, still other embodiments include controlling plants from the généra consisting of: Brachiaria or Urochloa.
A seventy-eighth embodiment includes the methods of controlling undesirable végétation comprising the step of applying a herbicidally effective amount of at least one mixture according to the thirty-sixth embodiment wherein the amount of the mixture is applied at a rate, expressed in gai/ha or gae/ha of methibenzuron selected from the group of rates and ranges of rates consisting of, about: 35, 70,140,280,560,700,1400, or 2800 within any range defined between any pair of the foregoing values.
A seventy-ninth embodiment includes the methods of controlling undesirable végétation comprising the step of applying a herbicidally effective amount of at least one mixture according to the thirty-seventh embodiment wherein the amount of the mixture is applied at a rate,
- 14expressed in gai/ha or gae/ha of metribuzin selected from the group of rates and ranges of rates consisting of, about: 25, 50,100,210,420, 840,1680,3360, or 5600 within any range defined between any pair of the foregoing values.
A eightieth embodiment includes the methods according to either of the thirty-seventh or seventy-ninth embodiments wherein the controlled plant is at least one plant selected from the group consisting of: CHEAL, KCHSC, LAMPU, SASKR, SETFA, SINAR, still other embodiments include controlling plants from the généra consisting of: Chenopodium, Kochia, Lamium, Salsola, Setaria, and Sinapsis.
A eighty-first embodiment includes the methods of controlling undesirable végétation comprising the step of applying a herbicidally effective amount of at least one mixture according to the thirty-eighth embodiment wherein the amount of the mixture is applied at a rate, expressed in gai/ha or gae/ha of propanil selected from the group of rates and ranges of rates consisting of, about: 60,120,420, 840,1680, 3360, or 5600 within any range defined between any pair of the foregoing values.
A eighty-second embodiment includes the methods according to either ofthe thirtyeighth or eighty-first embodiments wherein the controlled plant is at least one plant selected from the group consisting of: COMBE, ECHCG, ECHCO, IPOHE, and SCPMA, still other embodiments include controlling plants from the généra consisting of: Commelina, Echinochloa, Ipomoea, and Bolboschoenus or Schoenoplectus.
A eighty-third embodiment includes the methods of controlling undesirable végétation comprising the step of applying a herbicidally effective amount of at least one mixture according to the thirty-ninth embodiment wherein the amount of the mixture is applied at a rate, expressed in gai/ha or gae/ha of pyridate selected from the group of rates and ranges of rates consisting of, about: 25, 50,100,200,400, 800, or 1600 within any range defined between any pair of the foregoing values.
-15A eighty-fourth embodiment includes the methods of controlling undesirable végétation comprising the step of applying a herbicidally effective amount of at least one mixture according to the fortieth embodiment wherein the amount of the mixture is applied at a rate, expressed in gai/ha or gae/ha of siduron selected from the group of rates and ranges of rates consisting of, about: 70,140,280, 560,1120, 2240,4480, or 9000 within any range defined between any pair of the foregoing values.
A eighty-fifth embodiment includes the methods of controlling undesirable végétation comprising the step of applying a herbicidally effective amount of at least one mixture according to the forty-first embodiment wherein the amount of the mixture is applied at a rate, expressed in gai/ha or gae/ha of simazine selected from the group of rates and ranges of rates consisting of, about: 70,140,280, 560,1120, 2240,4480, or 8500 within any range defined between any pair of the foregoing values.
A eighty-sixth embodiment includes the methods according to either of the forty-first or eighty-fifth embodiments wherein the controlled plant is at least one plant selected from the group consisting of: BRAPP, ECHCG, ECHCO, CYPIR, and XANST, still other embodiments include controlling plants from the généra consisting of: Brachiaria or Urochloa, Echinochloa, Cyperus, and Xanthium.
A eighty-seventh embodiment includes the methods of controlling undesirable végétation comprising the step of applying a herbicidally effective amount of at least one mixture according to the forty-second embodiment wherein the amount of the mixture is applied at a rate, expressed in gai/ha or gae/ha of simetryne selected from the group of rates and ranges of rates consisting of, about: 25, 50, 112.5,225,450,900,1350, and 2000 within any range defined between any pair of the foregoing values.
A eighty-eighth embodiment includes the methods according to either of the forty-second or eighty-seventh embodiments wherein the controlled plant is at least one plant selected from
-16the group consisting of: CYPIR, CYPRO, ECHCO, ECHOR, FIMMI, and LEFCH, still other embodiments include controlling plants from the généra consisting of: Cyperus, Echinochloa, Fimbristylis, and Leptochloa.
A eighty-ninth embodiment inciudes the methods of controlling undesirable végétation comprising the step of applying a herbicidally effective amount of at least one mixture according to the forty-third embodiment wherein the amount of the mixture is applied at a rate, expressed in gai/ha or gae/ha of tebuthiuron selected from the group of rates and ranges of rates consisting of, about: 70,140,210,280,420,560, 840,1680,3360, and 4480 within any range defined between any pair of the foregoing values.
A ninetieth embodiment inciudes the methods according to either of the forty-third or eighty-ninth embodiments wherein the controlled plant is at least one plant selected from the group consisting of: BRSNN, CIRAR, CYPES, IPOHE, and XANST, still other embodiments include controlling plants from the généra consisting of: Brassica, Cirsium, Cyperus, Ipomoea, and Xanthium.
A ninety-first embodiment inciudes the methods of controlling undesirable végétation comprising the step of applying a herbicidally effective amount of at least one mixture according to the forty-fourth embodiment wherein the amount of the mixture is applied at a rate, expressed in gai/ha or gae/ha of terbuthylazine selected from the group of rates and ranges of rates consisting of, about: 60,125, 250,500,1000,1500, and 3000 within any range defined between any pair of the foregoing values.
A ninety-second embodiment inciudes the methods according to either of the forty-fourth or ninety-first embodiments wherein the controlled plant is at least one plant selected from the group consisting of: XANST, still other embodiments include controlling plants from the généra consisting of: Xanthium.
-17A ninety-third embodiment includes the composition of the first embodiment, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is atrazine.
A ninety-fourth embodiment includes the composition of the first embodiment, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is bentazon-sodium.
A ninety-fifth embodiment includes sition of the first embodiment, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is bromoxynil.
A ninety-sixth embodiment includes the composition of the first embodiment, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is chlorotoluron.
A ninety-seventh embodiment includes the composition of the first embodiment, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is cyanazine.
A ninety-eighth embodiment includes the composition of the first embodiment, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is diuron.
A ninety-ninth embodiment includes the composition of the first embodiment, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is hexazinone.
A one-hundredth embodiment includes the composition of the first embodiment, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is ioxynil.
A one-hundred-first embodiment includes the composition of the first embodiment, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is isoproturon.
-18A one-hundred-second embodiment includes the composition of the first embodiment, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is linuron.
A one-hundred-third embodiment includes the composition of the first embodiment, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is methibenzuron.
A one-hundred-fourth embodiment includes the composition of the first embodiment, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is metribuzin.
I
A one-hundred-fifth embodiment includes the composition of the first embodiment, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is propanil.
A one-hundred-sixth embodiment includes the composition of the first embodiment, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is pyridate.
A one-hundred-seventh embodiment includes the composition of the first embodiment, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is siduron.
A one-hundred-eighth embodiment includes the composition of the first embodiment, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is simazine.
A one-hundred-ninth embodiment includes the composition of the first embodiment, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b is simetryne.
-19A one-hundred-tenth embodiment includes the composition of the first embodiment, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is tebuthiuron.
A one-hundred-eleventh embodiment includes the composition of the first embodiment, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is terbuthylazine.
A one-hundred-twelfth embodiment includes the composition of the first embodiment, wherein the weight ratio of compound of formula (I) or agriculturally acceptable sait or ester thereof to atrazine or agriculturally acceptable sait or ester thereof is from about 1:2240 to about 6:1.
A one-hundred-thirteenth embodiment includes the composition of the first embodiment, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to bentazon or agriculturally acceptable sait thereof is from about 1:1120 to about 3:1.
A one-hundred-fourteenth embodiment includes the composition of the first embodiment, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to bromoxynil or agriculturally acceptable sait thereof is from about 1:280 to about 12:1.
A one-hundred-fifteenth embodiment includes the composition of the first embodiment, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to chlorotoluron or agriculturally acceptable sait or ester thereof is from about 1:1750 to about 1.5:1.
A one-hundred-sixteenth embodiment includes the composition ofthe first embodiment, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to cyanazine or agriculturally acceptable sait thereof is from about 1:2650 to about 6:1.
A one-hundred-seventeenth embodiment includes the composition of the first embodiment, wherein the weight ratio of the compound of formula (I) or agriculturally
-20acceptable sait or ester thereof to diuron of agriculturally acceptable thereof is from about
1:3600 to about 6:1.
A one-hundred-eighteenth embodiment includes the composition of the first embodiment, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to hexazinone or agriculturally acceptable sait thereof is from about 1:2500 to about 12:1.
A one-hundred-nineteenth embodiment includes the composition of the first embodiment, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to ioxynil or agriculturally acceptable sait thereof is from about 1:200 to about 12:1.
A one-hundred-twentieth embodiment includes the composition of the first embodiment, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to isoproturon or agriculturally acceptable sait thereof is from about 1:750 to about 12:1.
A one-hundred-twenty-first embodiment includes the composition of the first embodiment, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to linuron or agriculturally acceptable sait thereof is from about 1:2250 to about 6:1.
A one-hundred-twenty-second embodiment includes the composition of the first embodiment wherein the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to methibenzuron or agriculturally acceptable sait thereof is from about 1:1400 to about 4:1.
A one-hundred-twenty-third embodiment includes the composition of the first embodiment, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to metribuzin or agriculturally acceptable sait thereof is from about 1:2800 to about 6:1.
-21 A one-hundred-twenty-fourth embodiment includes the composition of the first embodiment, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to propanil or agriculturally acceptable sait thereof is from about 1:2800 to about 1:1.
A one-hundred-twenty-fifth embodiment includes the composition of the first embodiment, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to pyridate or agriculturally acceptable sait thereof is from about 1:800 to about 12:1.
A one-hundred-twenty-sixth embodiment includes the composition of the first embodiment, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to siduron or agriculturally acceptable sait thereof is from about 1:4500 to about 2:1.
A one-hundred-twenty-seventh embodiment includes the composition of the first embodiment, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to simazine or agriculturally acceptable sait thereof is from about 1:4250 to about 2:1.
A one-hundred-twenty-eighth embodiment includes the composition of the first embodiment, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to simetryne or agriculturally acceptable sait thereof is from about 1:1000 to about 12:1.
A one-hundred-twenty-ninth embodiment includes the composition of the first embodiment, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable sait or ester thereof to tebuthiuron or agriculturally acceptable sait thereof is from about 1:2240 to about 2:1.
-22A one-hundred-thirtieth embodiment includes the composition of the first embodiment, wherein the weight ratio of the compound of formula (I) or âgriculturally acceptable sait or ester thereof to terbuthylazine or âgriculturally acceptable thereof is from about 1:1500 to about 3:1.
A one-hundred-thirty-first embodiment includes the composition of any of ninety fourth to one-hundred-thirtieth embodiments which is synergistic as determined by the Colby équation.
Provided herein are herbicidal compositions comprising and methods of controlling undesirable végétation utilizing a herbicidally effective amount of(a) a compound ofthe formula (I)
NH,
Cl
OH or an âgriculturally acceptable sait or ester of thereof, and (b) a PS II inhibitor selected from the group consisting of: atrazine, bentazon, bentazon-sodium, bromoxynil, bromoxynil octanoate, chlorotoluron, cyanazine, diuron, hexazinone, ioxynil, isoproturon, linuron, methibenzuron, metribuzin, propanil, pyridate, siduron, simazine, simetryne, tebuthiuron and terbuthylazine, or dérivative, e.g., sait or ester thereof. The compositions may also contain an âgriculturally acceptable adjuvant or carrier.
Detailed Description
DEFINITIONS
As used herein, the compound of formula (I) has the following structure:
NH,
Cl
OH
The compound of formula (I) can be identified by the name 4-amino-3-chloro-6-(4-chloro-2fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylic acid and has been described in U.S. Patent 7,314,849 (B2), which is incorporated herein by reference in its entirety. Exemplary uses
-23of the compound of the formula (I) include controlling undesirable végétation, including grass, broadleaf and sedge weeds, in multiple non-crop and cropping situations.
Atrazine is 6-chloro-2V-ethyl-JV'-(l-methylethyl)-l,3,5-triazine-2,4-diamine. Its herbicidal activity is described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of atrazine include its use for pre-emergence and post-emergence control of broadleaf and grass weeds, e.g., in corn, sorghum, turf, sugar cane and other crops. Atrazine possesses the following structure:
h3c
Cl
H H
Bentazon is 3-(l-methylethyl)-177-2,l,3-benzothiadiazin-4(377)-one 2,2-dioxide. Its herbicidal activity is described in The Pesticide Manual, Fifteenth Edition, 2009. It is also known as bentazone. Bentazon has been used as its sodium sait, bentazon sodium. Exemplary uses of bentazon include its use for control of broadleaf and sedge weeds in broadleaf and grass crops. Bentazon possesses the following structure:
Bromoxynil is 3,5-dibromo-4-hydroxybenzonitrile. Its herbicidal activity is described in The Pesticide Manual, Fifteenth Edition, 2009. Bromoxynil has been used as its octanoate ester, bromoxynil octanoate. Exemplary uses of bromoxynil include its use for post-emergence control ofbroad-leaved weeds, e.g., in cereals, ryegrass-seed crops, turf, maize, and sorghum. It possesses the following structure:
Br
Chlorotoluron is 2V'-(3-chloro-4-methylphenyl)-2V,Ar-dimethylurea. Its herbicidal activity is described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of chlorotoluron include its use for control of broad-leaved and grass weeds, e.g., in winter cereals. It possesses the following structure:
Cyanazine is 2-[[4-chloro-6-(ethylamino)-l,3,5-triazin-2-yl]amino]-2methylpropanenitrile. Its herbicidal activity is described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of cyanazine include its use for pre-emergent control of weeds in beans, maize and peas and post-emergent control of weeds in early barley and wheat. It possesses the following structure:
Diuron is W-CS^-dichlorophenylJ-W.W-dimethylurea. Its herbicidal activity is described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of diuron include its use for pre-emergence and post-emergence control of broadleaf and grass weeds in, e.g., com, sorghum, sugar cane, citrus and other crops. Diuron possesses the following structure:
Hexazinoneis 3-cyclohexyl-6-(dimethylamino)-l-methyl-l,3,5-triazine-2,4(1//,3//)dione. Its herbicidal activity is described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of hexazinone include its use for post-emergent control of annual, biennial and perennial weeds in alfalfa, pineapples, sugar cane and conifers. It possesses the following structure:
ÇH3
Ioxynil is 4-hydroxy-3,5-diiodobenzonitrile. Its herbicidal activity is described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of ioxynil include its use for postemergence control of annual broad-leaved weeds in cereals, onions, leeks, garlic, shallots, flax, sugar cane, forage grasses, lawns and newly-sown turf. It possesses the following structure:
Isoproturon is Ar,A7-dimethyl-7V’-[4-(l-methylethyl)phenyl]urea. Its herbicidal activity is described in The Pesticide Manuai, Fifteenth Edition, 2009. Exemplary uses of isoproturon include its use for pre- and post-emergence control of annual grasses and annual broad-leaved weeds, e.g., in spring and winter wheat, spring and winter barley, winter rye and tritcale. It possesses the following structure:
O
Linuron is ^-(S^-dichlorophenylj-TV-methoxy-TV-methylurea. Its herbicidal activity is described in The Pesticide Manuai, Fifteenth Edition, 2009. Exemplary uses of linuron include its use for pre- and post-emergence control of annual grass and broad-leaved weeds, as well as seedling perennial weeds in asparagus, artichokes, carrots, parsley, fennel, parsnips, herbs and spices, celery, celeriac, onions, leeks, garlic, potatoes, peas, field beans, soya beans, cereals, maize, sorghum, cotton, flax, sunflowers, sugar cane, omamentals, established vines, bananas, cassava, coffee, tea, rice, peanuts, omamental trees and shrubs, and other crops. It possesses the following structure:
Cl
Cl
Methibenzuron is N-2-benzothiazolyl-N,N'-dimethylurea. Methibenzuron is also known as methabenzthiazuron. The herbicidal activity methibenzuron is described in The Pesticide Manuai, Fifteenth Edition, 2009. Exemplary uses of methibenzuron include its use for broadspectrum control of broad-leaved weeds and grasses, e.g., in cereals, legumes, maize, garlic and onions. It possesses the following structure:
Metribuzin is 4-amino-6-(l, 1 -dimethylethyl)-3-(methylthio)-1,2,4-triazin-5(477)-one. Its herbicidal activity is described in The Pesticide Manuai, Fifteenth Edition, 2009. Exemplary
-26uses of metribuzin include its use for pre-emergence and post-emergence control of broadleaf weeds, e.g., in soybeans, potatoes, corn, vegetables and other crops. Metribuzin possesses the following structure:
H3C h3c
Propanil is N-(3,4-dichlorophenyl)propanamide. Its herbicidal activity is described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of propanil include its use for post-emergence control of broadleaf and grass weeds in, e.g., rice. It possesses the following structure:
Pyridate is 0-(6-chloro-3-phenyl-4-pyridazinyl) S-octyl carbonothioate. Its herbicidal activity is described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of pyridate include its use for post-emergence control of annual broad-leaved weeds and grass weeds, e.g., in maize, sweet corn, oilseed râpe, cereals, rice, peanuts and vegetables. It possesses the following structure:
Cl
Siduron is AL(2-methylcyclohexyl)-Ar-phenylurea. Its herbicidal activity is described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of siduron include its use for pre-emergence control of Digitaria spp. and annual grass weeds in, e.g., turf farms, grass seed production and established turf. It possesses the following structure:
H H
Simazine is 6-chloro-Æ,N'-diethyl-1,3,5-triazine-2,4-diamine. Its herbicidal activity is described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of simazine include its use for control of germinating annual grasses and broad-leaved weeds in, e.g., pome fruit,
-27stone fruit, bush and cane fruit, citrus fruit, vines, strawberries, nuts, olives, pineapples, field beans, French beans, pea, maize, sweet com, asparagus, hops, alfalfa, lupins, oilseed râpe, artichokes, sugar cane, cocoa, coffee, rubber, oil palms, tea, turf and omamentals. It possesses the following structure:
Simetryne is W'-diethyl-6-(methylthio)-l,3,5-triazine-2,4-diamine. Simetryne is simetryn. Its herbicidal activity is described in The Pesticide Manual, Fifteenth Edition, 2009.
Exemplary uses of simetryn include its use for control of broad-leaved weeds, e.g., in rice. It possesses the following structure:
h3c\ 3 S
Tebuthiuron is TV-[5-( 1,1 -dimethylethyl)-1,3,4-thiadi azol-2-yl] -N,N-dimethylurea. Its herbicidal activity is described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of tebuthiuron include its use for control of herbaceous and woody plants, annual weeds, and many perennial grass and undersirable woody plants in pastures and rangeland, and control of grass and broadleaved weeds in sugar cane. It possesses the following structure:
Terbuthylazine is 6-chloro-7V-(l,l-dimethylethyl)-7V-ethyl-l,3,5-triazine-2,4-diamine. Its herbicidal activity is described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of terbuthylazine include its use for pre and post-emergence weed control, e.g., in maize, sorghum, vines, fruit trees, citrus, coffee, oil palm, cocoa, olives, potatoes, peas, beans, sugarcane, rubber, and forestry (tree nurseries and new plantings). It possesses the following structure:
L·
-28C1 N^N CH, il A 1^¾ H,C N N N CH, H H
As used herein, herbicide means a compound, e.g., active ingrédient that kills, controls or otherwise adversely modifies the growth of plants.
As used herein, a herbicidally effective or végétation controlling amount is an amount of active ingrédient which causes an adversely modifying effect to the végétation e.g., causing déviations from natural development, killing, effecting régulation, causing desiccation, causing retardation, and the like.
As used herein, controlling undesirable végétation means preventing, reducing, killing, or otherwise adversely modifying the development of plants and végétation. Described herein are methods of controlling undesirable végétation through the application of certain herbicide combinations or compositions. Methods of application include, but are not limited to applications to the végétation or locus thereof, e.g., application to the area adjacent to the végétation, as well as pre-emergence, post-emergence, foliar (broadcast, directed, banded, spot, mechanical, over-the-top, or rescue), and in-water applications (emerged and submerged végétation, broadcast, spot, mechanical, water-injected, granular broadcast, granular spot, shaker bottle, or stream spray) via hand, backpack, machine, tractor, or aerial (airplane and helicopter) application methods.
As used herein, plants and végétation include, but are not limited to, germinant seeds, emerging seedlings, plants emerging from végétative propagules, immature végétation, and established végétation.
As used herein, agriculturally acceptable salts and esters refer to salts and esters that exhibit herbicidal activity, or that are or can be converted in plants, water, or soil to the referenced herbicide. Exemplary agriculturally acceptable esters are those that are or can be hydrolyzed, oxidized, metabolized, or otherwise converted, e.g., in plants, water, or soil, to the corresponding carboxylic acid which, depending on the pH, may be in the dissociated or undissociated form.
Exemplary salts include those derived from alkali or alkaline earth metals and those derived from ammonia and amines. Exemplary cations include sodium, potassium, magnésium, and aminium cations of the formula:
r'r2r3r4n+
-29wherein R1, R2, R3 and R4 each, independently represents hydrogen or C1-C12 alkyl, C3-C12 alkenyl or C3-C12 alkynyl, each of which is optionally substituted by one or more hydroxy, C1-C4 alkoxy, C1-C4 alkylthio or phenyl groups, provided that R1, R2, R3 and R4 are sterically compatible. Additionally, any two of R1, R2, R3 and R4 together may represent an aliphatic difunctional moiety containing one to twelve carbon atoms and up to two oxygen or sulfur atoms. Salts can be prepared by treatment with a métal hydroxide, such as sodium hydroxide, with an amine, such as ammonia, trimethylamine, diethanolamine, 2-methylthiopropylamine, bisallylamine, 2-butoxyethylamine, morpholine, cyclododecylamine, or benzylamine or with a tetraalkylammonium hydroxide, such as tétraméthylammonium hydroxide or choline hydroxide.
Exemplary esters include those derived from C1-C12 alkyl, C3-C12 alkenyl, C3-C12 alkynyl or C7-C10 aryl-substituted alkyl alcohols, such as methyl alcohol, isopropyl alcohol, 1-butanol, 2ethylhexanol, butoxyethanol, methoxypropanol, allyl alcohol, propargyl alcohol, cyclohexanol or unsubstituted or substituted benzyl alcohols. Benzyl alcohols may be substituted with from 13 substituents independently seiected 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)
NH,
Cl
OH or an agriculturally acceptable sait or ester of thereof, and (b) a PS II inhibitor seiected from the group consisting of atrazine, bentazon, bentazon-sodium, bromoxynil, bromoxyml octanoate, chlorotoluron, cyanazine, diuron, hexazinone, ioxynil, isoproturon, linuron,
-30methibenzuron, metribuzin, propanil, pyridate, siduron, simazine, simetryne, tebuthiuron and terbuthylazine, or a sait or ester thereof.
Provided herein are also methods of controlling undesirable végétation comprising contacting the végétation or the locus thereof, i.e., the area adjacent to the undesirable végétation, with or applying to the soil or water to prevent the emergence or growth of végétation a herbicidally effective amount of the compound of formula (I) or agriculturally acceptable sait or ester thereof and (b) a PS II inhibitor selected from the group consisting of atrazine, bentazon, bentazon-sodium, bromoxynil, bromoxynil octanoate, chlorotoluron, cyanazine, diuron, hexazinone, ioxynil, isoproturon, linuron, methibenzuron, metribuzin, propanil, pyridate, siduron, simazine, simetryne, tebuthiuron and terbuthylazine, or a sait or ester thereof. In certain embodiments, the methods employ the compositions described herein.
Furthermore, in some embodiments, the combination of compound (I) or agriculturally acceptable sait or ester thereof and a PS II inhibitor or an agriculturally acceptable sait or ester thereof exhibits synergism, e.g., the herbicidal active ingrédients are more effective in combination than when applied individually. The Herbicide Handbook of the Weed Science Society of America, Ninth Edition, 2007, p. 429 notes that “‘synergism’ [is] 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.” 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 carboxyiate sait of the compound of formula (I) is employed. In certain embodiments, an aralkyl or alkyl ester is employed. In certain embodiments, a benzyl, substituted benzyl, or Cm alkyl, e.g., n-butyl ester is employed. In certain embodiments, the benzyl ester is employed.
In some embodiments, the compound of formula (I) or sait or ester thereof and a PS II inhibitor, or an agriculturally acceptable sait or ester thereof are formulated in one composition, tank mixed, applied simultaneously, or applied sequentially.
Herbicidal activity is exhibited by the compounds when they are applied dîrectly to the plant or to the locus of the plant at any stage of growth. The effect observed dépends upon the plant species to be controlled, the stage of growth of the plant, the application parameters of dilution and spray drop size, the particle size of solid components, the environmental conditions at the time of use, the spécifie compound employed, the spécifie adjuvants and carriers employed, the soil type, and the like, as well as the amount of chemical applied. These and other
-31 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, sugarbeet, 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 on 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-, triazolopyrimidine-tolerant-, sulfonylaminocarbonyltriazolinone-tolerant-, acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitor-tolerant-, 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor -tolérant-, phytoene desaturase inhibitor-tolerant-, carotenoid biosynthesis inhibitor-tolerant-, protoporphyrinogen oxidase (PPO) inhibitor -tolérant-, cellulose biosynthesis inhibitor-tolerant-, mitosis inhibitor-tolerant-, microtubule inhibitor-tolerant-, very long chain fatty acid inhibitor-tolerant-, fatty acid and lipid biosynthesis inhibitor-tolerant-, photosystem I inhibitor-tolerant-, photosystem II inhibitor-tolerant-, triazine-tolerant-, and bromoxynil-tolerant- crops (such as, but not limited to, soybean, cotton, canola/oilseed râpe, rice, cereals, com, sorghum, sunflower, sugarbeet, 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, ACCase inhibitors, cyclohexanediones, phenylpyrazolines, imidazolinones, sulfonylureas, pyrimidinylthiobenzoates,
-32triazolopyrimidines, sulfonylaminocarbonyltriazolinones, ALS or AHAS inhibitors, HPPD inhibitors, phytoene desaturase inhibitors, carotenoid biosynthesis inhibitors, PPO inhibitors, cellulose biosynthesis inhibitors, mitosis inhibitors, microtubule inhibitors, very long chain fatty acid inhibitors, fatty acid and lipid biosynthesis inhibitors, photosystem I inhibitors, photosystem II inhibitors, triazines, and bromoxynil. The compositions and methods may be used in controlling undesirable végétation in crops possessing multiple or stacked traits conferring tolérance to multiple chemistries and/or inhibitors of multiple modes of action.
In some embodiments, the compound of formula (I) or sait or ester thereof and complementary herbicide or sait or ester thereof are used in combination with herbicides that are sélective for the crop being treated and which complément the spectrum of weeds controlled by these compounds at the application rate 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, or sequentially.
The compositions and methods may be used in controlling undesirable végétation in crops possessing agronomie stress tolérance (including but not limited to drought, cold, heat, sait, water, nutrient, fertility, pH), pest tolérance (including but not limited to insects, fungi and pathogens) and crop improvement traits (including but not limited to yield; protein, carbohydrate, or oil content; protein, carbohydrate, or oil composition; plant stature and plant architecture).
The compositions and methods provided herein are utilized to control undesirable végétation. Undesirable végétation includes, but is not limited to, undesirable végétation that occurs in rice, cereals, wheat, barley, oats, rye, sorghum, com/maize, sugarcane, sunflower, oilseed râpe, canola, sugar beet, 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 some embodiments, the methods provided herein are utilized to control undesirable végétation in rice. In certain embodiments, the undesirable végétation 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. (bamyardgrass, ECHCG), Echinochloa crus-pavonis (Kunth) Schult. (gulf cockspur, ECHCV), Echinochloa colonum (L.) LINK (junglerice, ECHCO), Echinochloa oryzoides (Ard.) Fritsch (early watergrass, ECHOR), Echinochloa oryzicola (Vasinger) Vasinger (late watergrass, ECHPH), Echinochloa phyllopogon (Stapf) Koso-Pol. (rice bamyardgrass, ECHPH), Echinochloa polystachya (Kunth) Hitchc. (creeping
-33river 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 dilatation 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 firingerush, 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), Altemantheraphiloxeroides (Mart.) Griseb. (alligatorweed, ALRPH), Alismaplantago-aquatica L. (common waterplantain, ALSPA), Amaranthus species, (pigweeds and amaranths, AMASS), Ammannia coccinea Rottb. (redstem, AMMCO), Commelina benghalensis L. (Benghal dayflower, COMBE), Eclipta alba (L.) Hassk. (American false daisy, ECLAL), Heteranthera limosa (SW.) Willd./Vahl (ducksalad, HETLI), Heteranthera reniformis R. & P. (roundleaf mudplantain, HETRE), Ipomoea species (momingglories, IPOSS), Ipomoea hederacea (L.) Jacq. (ivyleaf momingglory, IPOHE), Lindemia dubia (L.) Pennell (low false pimpemel, LIDDU), Ludwigia species (LUDSS), Ludwigia linifolia Poir. (southeastem primrose-willow, LUDLI), Ludwigia octovalvis (Jacq.) Raven (longfruited primrose-willow, LUDOC), Monochoria korsakowii Regel & Maack (monochoria, MOOKA), Monochoria vaginalis (Burm. F.) C. Presl ex Kuhth, (monochoria, MOOVA), Murdannia nudiflora (L.) Brenan (doveweed, MUDNU), Polygonum pensylvanicum L., (Pennsylvania smartweed, POLPY), Polygonum persicaria L. (ladysthumb, POLPE), Polygonum hydropiperoides Michx. (POLHP, mild smartweed), Rotala indica (Willd.) Koehne (Indian toothcup, ROTIN), Sagittaria species, (arrowhead, SAGSS), Sesbania exaltata (Raf.) Cory/Rydb. Ex Hill (hemp sesbania, SEBEX), or Sphenoclea zeylanica Gaertn. (gooseweed, SPDZE).
In some embodiments, the methods provided herein are utilized to control undesirable végétation in cereals. In certain embodiments, the undesirable végétation is Alopecurus myosuroides Huds. (blackgrass, ALOMY), Apera spica-venti (L.) Beauv. (windgrass, APESV), Avena fatua L. (wild oat, AVEFA), Bromus tectorum L. (downy brome, BROTE), Lolium
-34multiflorum 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, CIRARJ, 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), Veronicapersica Poir. (Persian speedwell, VERPE), Viola arvensis Murr. (field violet, VIOAR), or Viola tricolor L. (wild violet, VIOTR).
In some embodiments, the methods provided herein are utilized to control undesirable végétation in range and pasture, fallowland, IVM and ROW. In certain embodiments, the undesirable végétation is Ambrosia artemisiifolia L. (common ragweed, AMBEL), Cassia obtusifolia (sickle pod, CASOB), Centaurea maculosa auct. non Lam. (spotted knapweed, CENMA), Cirsium arvense (L.) Scop. (Canada thistle, CIRAR), Convolvulus arvensis L. (field bindweed, CONAR), Daucus carota L. (wild carrot, DAUCA), Euphorbia esula L. (leafy spurge, EPHES), Lactuca serriola L./Tom. (prickly lettuce, LACSE), Plantago lanceolata L. (buckhom plantain, PLALA), Rumex obtusifolius L. (broadleaf dock, RUMOB), Sida spinosa L. (prickly sida, SIDSP), Sinapis arvensis L. (wild mustard, SINAR), Sonchus arvensis L. (perennial sowthistle, SONAR), Solidago species (goldenrod, SOOSS), Taraxacum officinale G.H. Weber ex Wiggers (dandelion, TAROF), Trifolium repens L. (white clover, TRFRE), or Urtica dioica L. (common nettle, URTDI).
In some embodiments, the methods provided herein are utilized to control undesirable végétation found in row crops, tree and vine crops, and perennial crops. In certain embodiments, the undesirable végétation is Alopecurus myosuroides Huds. (blackgrass, ALOMY), Avenafatua 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), Brachiariaplantaginea (Link) Hitchc. or Urochloaplantaginea (Link) R.D. Webster (alexandergrass, BRAPL), Cenchrus echinatus L. (southem sandbur, CENEC), Digitaria
-35horizontalis Willd. (Jamaican crabgrass, DIGHO), Digitaria insularis (L.) Mez ex Ekman (sourgrass, TRCIN), Digitaria sanguinalis (L.) Scop. (large crabgrass, DIGSA), Echinochloa crus-galli (L.) P. Beauv. (bamyardgrass, ECHCG), Echinochloa colonum (L.) Link (junglerice, ECHCO), Eletisine indica (L.) Gaertn. (goosegrass, ELEIN), Lolitim multiflorum Lam. (Italian ryegrass, LOLMU), Panicum dichotomiflorum Michx. (fall panicum, PANDI), Panicwn 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. (puiple 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), Asclépios syriaca L. (common milkweed, ASCSY), Bidenspilosa L. (hairy beggarticks, BIDPI), Borreria species (BOISS), Borreria alata (Aubl.) DC. or Spermacoce alata Aubl. (broadleaf buttonweed, BOILF), Spermacose latifolia (broadleaved button weed, BOILF), Chenopodium album L. (common lambsquarters, CHEAL), Cirsium arvense (L.) Scop. (Canada thistle, CIRAR), Commelina benghalensis L. (tropical spiderwort, COMBE), Datura stramonium L. (jimsonweed, DATST), Daucus carota L. (wild 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 momingglory, IAQTA), Ipomoea hederacea (L.) Jacq. (ivyleaf momingglory, IPOHE), Ipomoea lacunosa L. (white momingglory, IPOLA), Lactuca serriola L./Tom. (prickly lettuce, LACSE), Portulaca oleracea L. (common purslane, POROL), Richardia species (pusley, RCHSS), Sida species (sida, SIDSS), Sida spinosa L. (prickly sida, SIDSP), Sinapis arvensis L. (wild mustard, SINAR), Solanum ptychanthum Dunal (eastem black nightshade, SOLPT), Tridax procumbens L. (coat buttons, TRQPR), or Xanthium strumarium L. (common cocklebur, XANST).
In some embodiments, the methods provided herein are utîlized to control undesirable végétation in turf. In certain embodiments, the undesirable végétation is Bellis perennis L. (English daisy, BELPE), Cyperus esculentus L. (yellow nutsedge, CYPES), Cyperus species
-36(CYPSS), Digitaria sanguinalis (L.) Scop. (large crabgrass, DIGSA), Diodia virginiana L. (Virginia buttonweed, DIQVI), Euphorbia species (spurge, EPHSS), Glechoma hederacea L. (ground ivy, GLEHE), Hydrocotyle umbellata L. (dollarweed, HYDUM), Kyllinga species (kyllinga, KYLSS), Lamium amplexicaule L. (henbit, LAMAM), Murdannia nudiflora (L.) Brenan (doveweed, MUDNU), Oxalis species (woodsorrel, OXASS), Plantago major L. (broadleaf plantain, PLAMA), Plantago lanceolata L. (buckhom/narrowleaf plantain, PLALA), Phyllanthus urinaria L. (chamberbitter, PYLTE), Rumex obtusifolius L. (broadleaf dock, RUMOB), Stachys floridana Shuttlew. (Florida betony, STAFL), Stellaria media (L.) Vill. (common chickweed, STEME), Taraxacum officinale G.H. Weber ex Wiggers (dandelion, TAROF), Trifolium repens L. (white clover, TRFRE), or Viola species (wild violet, VIOSS).
In some embodiments, the compositions and methods provided herein are utilized to control undesirable végétation consisting of grass, broadleaf and sedge weeds. In certain embodiments, the compositions and methods provided herein are utilized to control undesirable végétation including Abutilon, Amaranthus, Brachiaria or Urochloa, Brassica, Chenopodium, Commelina, Cyperus, Echinochloa, Fimbristylis, Galium, Ipomoea, Kochia, Lamium, Leptochïoa, Salsola, Setaria, Sinapis, Veronica, Xanthium, Bolboschoenus, Schoenoplectus, Sinapis, Veronica, and Xanthium species.
In some embodiments, the combination of compound (I) or agriculturally acceptable ester or sait thereof and a PS II inhibitor or an agriculturally acceptable sait or ester thereof is used to control Abutilon theophrasti Medik. (velvetleaf, ABUTH), Amaranthus retroflexus L. (redroot pigweed, AMARE), Brachiaria platyphylla (Groseb.) Nash or Urochloa platyphylla (Nash) R.D. Webster (broadleaf signalgrass, BRAPP), Brassica napus L. (oilseed râpe, BRSNW), Chenopodium album L. (common lambsquarters, CHEAL), Commelina benghalensis L. (Benghal dayflower, COMBE), Cyperus iria L. (rice flatsedge, CYPIR), Cyperus rotundus L. (purple nutsedge, CYPRO), Echinochloa crus-galli (L.) Beauv. (bamyardgrass, 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 momingglory, IPOHE), Kochia scoparia (L.) Schrad. (kochia, KCHSC), Lamium purptireum L. (purple deadnettle, LAMPU), Leptochïoa chinensis (L.) Nees (Chinese sprangletop, LEFCH), Bolboschoenus maritimus (L.) Palla or Schoenoplectus maritimus (L.) Lye (sea clubrush, SCPMA), Salsola tragus L. (Russian thistle, SASKR), Setaria faberi Herrm. (giant foxtail, SETFA), Setaria viridis (L.) Beauv. (green foxtail, SETVI), Sinapis arvensis L. (wild mustard, SINAR), and Veronica
-37persica Poir. (Persian speedwell, VERPE), Xanthium strumarium L. (common cocklebur, XANST).
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) inhibltors (e.g., imidazolinones, sulfonylureas, pyrimidinylthiobenzoates, triazolopyrimidines, sulfonylaminocarbonyltriazolinones), photosystem II inhibltors (e.g., phenylcarbamates, pyridazinones, triazines, triazinones, uracils, amides, ureas, benzothiadiazinones, nitriles, phenylpyridazines), acetyl CoA carboxylase (ACCase) inhibltors (e.g., aryloxyphenoxypropionates, cyclohexanediones, phenylpyrazolines), synthetic auxins, (e.g., benzoic acids, phenoxycarboxylic acids, pyridine carboxylic acids, quinoline carboxylic acids), auxin transport inhibltors (e.g., phthalamates, semicarbazones), photosystem I inhibltors (e.g., bipyridyliums), 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibltors, (e.g., glyphosate), glutamine synthetase inhibltors (e.g., glufosinate, bialafos), microtubule assembly inhibltors, (e.g., benzamides, benzoic acids, dinitroanilines, phosphoramidates, pyridines), mitosis inhibltors (e.g., carbamates), very long chain fatty acid (VLCFA) inhibltors (e.g., acetamides, chloroacetamides, oxyacetamides, tetrazolinones), fatty acid and lipid synthesis inhibltors (e.g., phosphorodithioates, thiocarbamates, benzofiiranes, chlorocarbonic acids), protoporphyrinogen oxidase (PPO) inhibltors (e.g., diphenylethers, N-phenylphthalimides, oxadiazoles, oxazolidinediones, phenylpyrazoles, pyrimidindiones, thiadiazoles, triazolinones), carotenoid biosynthesis inhibltors (e.g., clomazone, amitrole, aclonifen), phytoene desaturase (PDS) inhibltors (e.g., amides, anilidex, fiiranones, phenoxybutan-amides, pyridiazinones, pyridines), 4-hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibltors (e.g., callistemones, isoxazoles, pyrazoles, triketones), cellulose biosynthesis inhibltors (e.g., nitriles, benzamides, quinclorac, triazolocarboxamides), herbicides with multiple modes-of-action such as quinclorac, and unclassified herbicides such as arylaminopropionic acids, difenzoquat, endothall, and organoarsenicals. Exemplary résistant or tolérant weeds include, but are not limited to, biotypes with résistance or tolérance to multiple herbicides, biotypes with résistance or tolérance to multiple chemical classes, biotypes with résistance or tolérance to multiple herbicide modes-ofaction, and biotypes with multiple résistance or tolérance mechanisms (e.g., target site résistance or metabolic résistance).
-38In some embodiments, an agriculturally acceptable ester or sait of bentazon is employed in the methods or compositions described herein. In certain embodiments, the sodium sait of bentazon is employed.
In some embodiments, an agriculturally acceptable ester or sait of ioxynil is employed in the methods or compositions described herein. In certain embodiments, the sodium sait of ioxynil is employed. In certain embodiments, the potassium sait of ioxynil is employed. In certain embodiments, the octanoate ester of ioxynil is employed.
In some embodiments, an agriculturally acceptable ester or sait of bromoxynil is employed in the methods or compositions described herein. In certain embodiments, the potassium sait of bromoxynil is employed. In certain embodiments, the butyl ester of bromoxynil is employed. In certain embodiments, the heptyl ester of bromoxynil is employed. In certain embodiments, the octanoate ester of bromoxynil is employed.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or sait or ester thereof is used in combination with atrazine or sait thereof. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to atrazine or sait thereof is within the range from about 1:2200 to about 6:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to atrazine or sait thereof is within the range from 1:509 to about 1:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to atrazine or sait thereof is within the range from about 1:512 to about 1:8. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to atrazine or sait thereof is within the range from about 1:256 to about 1:16. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to atrazine or sait thereof is within the range from about 1:256 to about 1:9. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl ester and atrazine or sait thereof. In one embodiment, the composition comprises the compound of formula (I) and atrazine or sait thereof, wherein the weight ratio of the compound of formula (I) to atrazine or sait thereof is about 1:256 to about 1:32. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and atrazine or sait thereof, wherein the weight ratio of the benzyl ester of the compound of formula (I) to atrazine or sait thereof is about 1:130 to about 1:16. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and atrazine or sait thereof, wherein the weight ratio of the benzyl ester of the compound of formula (I) to atrazine or sait thereof is about 1:140 to about 1:17.5. With respect to the methods, in certain embodiments, the methods comprise contacting the
-39undesirable 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 from about 52 grams active ingrédient per hectare (g ai/ha) to about 4700 g ai/ha based on the total amount of active ingrédients in the composition. In certain embodiments, the composition is applied at an application rate from about 60 grams active ingrédient per hectare (g ai/ha) to about 2300 g ai/ha based on the total amount of active ingrédients in the composition. In some embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation with a compound of formula (I) or sait or ester thereof and atrazine or sait thereof, e.g., sequentially or simultaneously. In some embodiments, the atrazine or sait thereof is applied at a rate from about 50 g ai/ha to about 4400 g ai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 g ae/ha to about 300 g ae/ha. In some embodiments, the atrazine or sait thereof is applied at a rate from about 140 g ai/ha to about 2240 g ai/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 (g ae/ha) to about 35 g ae/ha. In some embodiments, the atrazine or sait thereof is applied at a rate from about 280 g ai/ha to about 1120 g ai/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 (g ae/ha) to about 35 g ae/ha. In certain embodiments, the methods utilize the compound of formula (I), or its benzyl ester and atrazine or sait thereof. In one embodiment, the methods utilize the compound of formula (I) and atrazine or sait thereof, wherein the compound of formula (I) is applied at a rate from about 4.38 g acid équivalent per hectare (g ae/ha) to about 8.75 g ae/ha, and atrazine or sait thereof is applied at a rate of about 280 g ai/ha to about 1120 g ai/ha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and atrazine or sait thereof, wherein the benzyl ester of the compound of formula (I) is applied at a rate from about 4.38 g acid équivalent per hectare (g ae/ha) to about 17.5 g ae/ha, and atrazine or sait thereof is applied at a rate of about 280 g ai/ha to about 560 g ai/ha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and atrazine or sait thereof, wherein the benzyl ester of the compound of formula (I) is applied at a rate from about 8 g acid équivalent per hectare (g ae/ha) to about 32 g ae/ha, and atrazine or sait thereof is applied at a rate of about 560 g ai/ha to about 1120 g ai/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or sait or ester thereof in combination with atrazine or sait thereof are used to control BRAPP, CYPIR, ECHCG, XANST orECHCO.
-40In certain embodiments of the compositions and methods described herein, the compound of formula (I) or sait or ester thereof is used in combination with bentazon or sait thereof. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to bentazon or sait thereof is within the range from about 1:1120 to about 3:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to bentazon or sait thereof is within the range from about 1:256 to about 1:1.2. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to bentazon or sait thereof is within the range from about 1:192 to about 1:3. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to is within the range from about 1:96 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 bentazon-sodium. In one embodiment, the composition comprises the compound of formula (I) and bentazon-sodium, wherein the weight ratio of the compound of formula (I) to bentazonsodium is about 1:96 to about 1:13. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and bentazon-sodium, wherein the weight ratio of the benzyl ester ofthe compound offormula (I) to bentazon-sodium is about 1:96 to about 1:3.4. In one embodiment, the composition comprises the n-butyl ester of the compound of formula (I) and bentazon-sodium, wherein the weight ratio of the n-butyl ester of the compound of formula (I) to bentazon-sodium is about 1:48 to about 1:16. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and bentazon-sodium, wherein the weight ratio of the benzyl ester of the compound of formula (I) to bentazon-sodium is about 1:13.7 to about 1:3.4. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation a composition described herein. In some embodiments, the composition is applied at an application rate from about 107 grams active ingrédient per hectare (g ai/ha) to about 2540 g ai/ha based on the total amount of active ingrédients in the composition. In certain embodiments, the composition is applied at an application rate from about 110 grams active ingrédient per hectare (g ai/ha) to about 1205 g ai/ha based on the total amount of active ingrédients in the composition. In some embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation with a compound of formula (I) or sait or ester thereof and bentazon or sait thereof, e.g., sequentially or simultaneously. In some embodiments, the bentazon or sait thereof is applied at a rate from about 105 g ai/ha to about 2240 g ai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from
-41 about 2 g ae/ha to about 300 g ae/ha. In some embodiments, the bentazon or sait thereof is applied at a rate from about 50 g ai/ha to about 2240 g ai/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 (g ae/ha) to about 140 g ae/ha. In some embodiments, the bentazon or sait thereof is applied at a rate from about 60 g ai/ha to about 1120 g ai/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 (g ae/ha) to about 84.4 g ae/ha. In certain embodiments, the methods utilize the compound of formula (I), or its benzyl or n-butyl ester and bentazon-sodium. In one embodiment, the methods utilize the compound of formula (I) and bentazon-sodium, wherein the compound of formula (I) is applied at a rate from about 4.38 g acid équivalent per hectare (g ae/ha) to about 84.8 g ae/ha, and bentazon-sodium is applied at a rate of about 105 g ai/ha to about 1120 g ai/ha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and bentazon-sodium, wherein the benzyl ester of the compound of formula (I) is applied at a rate from about 4.38 g acid équivalent per hectare (g ae/ha) to about 70 g ae/ha, and bentazon-sodium is applied at a rate of about 105 g ai/ha to about 1120 g ai/ha. In one embodiment, the methods utilize the n-butyl ester of the compound of formula (I) and bentazon-sodium, wherein the n-butyl ester of the compound of formula (I) is applied at a rate of about 17.5 g acid équivalent per hectare (g ae/ha) to about 70 g ae/ha, and bentazon-sodium is applied at a rate of about 840 g ai/ha to about 1120 g ai/ha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and bentazon-sodium, wherein the benzyl ester of the compound of formula (I) is applied at a rate from about 8.75 g acid équivalent per hectare (g ae/ha) to about 17.5 g ae/ha, and bentazonsodium is applied at a rate of about 60 g ai/ha to about 120 g ai/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or sait or ester thereof in combination with bentazon or sait thereof are used to control BRSNW, COMBE, ECHCG, ECHOR, IPOHE, LEFCH, SCPMA, or SETFA.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or sait or ester thereof is used in combination with bromoxynil or sait thereof. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to bromoxynil or sait thereof is within the range from about 1:280 to about 12:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to bromoxynil or sait thereof is within the range from about 1:254 to about 2:1. In certain embodiments, the weight ratio ofthe compound of formula (I) or sait or ester thereof to bromoxynil or sait thereof is within the range from about 1:18 to about 1:4. In certain embodiments, the compositions comprise the compound of formula (I) or its
-42benzyl or n-butyl ester and bromoxynil or sait thereof. 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 from about 27 grams active ingrédient per hectare (g ai/ha) to about 860 g ai/ha based on the total amount of active ingrédients in the composition. In certain embodiments, the composition is applied at an application rate from about 50 grams active ingrédient per hectare (g ai/ha) to about 610 g ai/ha based on the total amount of active ingrédients in the composition. In some embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation with a compound of formula (I) or sait or ester thereof and bromoxynil or sait thereof or sait thereof, e.g., sequentially or simultaneously. In some embodiments, the bromoxynil or sait thereof is applied at a rate from about 25 g ai/ha to about 560 g ai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 g ae/ha to about 300 g ae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and bromoxynil or sait thereof can be used to control AMARE, ECHCG, IPOHE, or SETFA.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or sait or ester thereof is used in combination with chlorotoluron or sait thereof. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to chlorotoluron or sait thereof is within the range from about 1:1750 to about 1.5:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to chlorotoluron or sait thereof is within the range from about 1:909 to about 1:4. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and chlorotoluron or sait thereof. 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 from about 202 grams active ingrédient per hectare (g ai/ha) to about 3800 g ai/ha based on the total amount of active ingrédients in the composition. In certain embodiments, the composition is applied at an application rate from about 203 grams active ingrédient per hectare (g ai/ha) to about 2500 g ai/ha based on the total amount of active ingrédients in the composition. In some embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation with a compound of formula (I) or sait or ester thereof and chlorotoluron
-43or sait thereof or sait thereof, e.g., sequentially or simultaneously. In some embodiments, the chlorotoluron or sait thereof is applied at a rate from about 200 g ai/ha to about 3500 g ai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 g ae/ha to about 300 g ae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and chlorotoluron or sait thereof.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or sait or ester thereof is used in combination with cyanazine or sait thereof. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to cyanazine or sait thereof is within the range from about 1:2650 to about 6:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to cyanazine or sait thereof is within the range from about 1:1600 to about 1:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to cyanazine or sait thereof is within the range from about 1:110 to about 1:5.3. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and cyanazine or sait thereof. 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 from about 52 grams active ingrédient per hectare (g ai/ha) to about 5600 g ai/ha based on the total amount of active ingrédients in the composition. In certain embodiments, the composition is applied at an application rate from about 53 grams active ingrédient per hectare (g ai/ha) to about 3550 g ai/ha based on the total amount of active ingrédients in the composition. In some embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation with a compound of formula (I) or sait or ester thereof and cyanazine or sait thereof, e.g., sequentially or simultaneously. In some embodiments, the cyanazine or sait thereof is applied at a rate from about 50 g ai/ha to about 5300 g ai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 g ae/ha to about 300 g ae/ha. In some embodiments, the cyanazine or sait thereof is applied at a rate from about 170 g ai/ha to about 880 g ai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 8 g ae/ha to about 32 g ae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and cyanazine or sait thereof for the control of BRAPP or IPOHE.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or sait or ester thereof is used in combination with diuron or sait
-44thereof. With regard to the compositions, in some embodiments, the weight ratio ofthe compound of formula (I) or sait or ester thereof to diuron or sait thereof is within the range from about 1: 3600 to about 6:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to diuron or sait thereof is within the range from about 1:509 to about 1:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to diuron or sait thereof is within the range from about 1:70 to about 1:9. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and diuron or sait thereof. 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 from about 52 grams active ingrédient per hectare (g ai/ha) to about 7500 g ai/ha based on the total amount of active ingrédients in the composition. In certain embodiments, the composition is applied at an application rate from about 55 grams active ingrédient per hectare (g ai/ha) to about 2300 g ai/ha based on the total amount of active ingrédients in the composition. In some embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation with a compound of formula (I) or sait or ester thereof and diuron or sait thereof or sait thereof, e.g., sequentially or simultaneously. In some embodiments, the diuron or sait thereof is applied at a rate from about 50 g ai/ha to about 7200 g ai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 g ae/ha to about 300 g ae/ha. In some embodiments, the diuron or sait thereof is applied at a rate from about 280 g ai/ha to about 1,120 g ai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 16g ae/ha to about 32 g ae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and diuron or sait thereof for the control of ABUTH, BRAPP, ECHCG, ECHCO, SETFA or SETVI.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or sait or ester thereof is used in combination with hexazinone or sait thereof. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to hexazinone or sait thereof is within the range from about 1:2500 to about 12:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to hexazinone or sait thereof is within the range from about 1:1360 to about 2:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to hexazinone or sait thereof is within the range from about 1:156 to about 1:19. In certain embodiments, the compositions comprise the compound of formula (I) or its
-45benzyl or n-butyl ester and hexazinone or sait thereof. 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 from about 27 grams active ingrédient per hectare (g ai/ha) to about 5300 g ai/ha based on the total amount of active ingrédients in the composition. In certain embodiments, the composition is applied at an application rate from about 28 grams active ingrédient per hectare (g ai/ha) to about 3050 g ai/ha based on the total amount of active ingrédients in the composition. In some embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation with a compound of formula (I) or sait or ester thereof and hexazinone or sait thereof, e.g., sequentially or simultaneously. In some embodiments, the hexazinone or sait thereof is applied at a rate from about 25 g ai/ha to about 5000 g ai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 g ae/ha to about 300 g ae/ha. In some embodiments, the hexazinone or sait thereof is applied at a rate from about 625 g ai/ha to about 1,250 g ai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 8 g ae/ha to about 32 g ae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and hexazinone or sait thereof for the control of ECHCO, ECHCG or IPOHE.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or sait or ester thereof is used in combination with ioxynil or sait thereof. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to ioxynil or sait thereof is within the range from about 1:200 to about 12:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to ioxynil or sait thereof is within the range from about 1:136 to about 6:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to ioxynil or sait thereof is within the range from about 1:38 to about 1:9. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and ioxynil or sait thereof. 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 from about 27 grams active ingrédient per hectare (g ai/ha) to about 700 g ai/ha based on the total amount of active ingrédients in the composition. In certain embodiments, the composition is applied at an
-46application rate from about 28 grams active ingrédient per hectare (g ai/ha) to about 450 g ai/ha based on the total amount of active ingrédients in the composition. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and ioxynil or sait thereof. 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 ioxynil or sait thereof is applied at a rate from about 25 g ai/ha to about 400 g ai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 g ae/ha to about 300 g ae/ha. In some embodiments, the ioxynil or sait thereof is applied at a rate from about 300 g ai/ha to about 400 g ai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 8 g ae/ha to about 32 g ae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and ioxynil or sait thereof for the control of IPOHE.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or sait or ester thereof is used in combination with isoproturon or sait thereof. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to isoproturon or sait thereof is within the range from about 1:750 to about 12:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to isoproturon or sait thereof is within the range from about 1:600 to about 1:37.5. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to isoproturon or sait thereof is within the range from about 1:455 to about 2:1. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and isoproturon or sait thereof. 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 from about 27 grams active ingrédient per hectare (g ai/ha) to about 1800 g ai/ha based on the total amount of active ingrédients in the composition. In certain embodiments, the composition is applied at an application rate from about 28 grams active ingrédient per hectare (g ai/ha) to about 1050 g ai/ha based on the total amount of active ingrédients in the composition. In some embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation with a compound of formula (I) or sait or ester thereof and isoproturon or sait thereof, e.g., sequentially or simultaneously. In some embodiments, the isoproturon or sait thereof is applied at a rate from
-47âbout 25 g ai/ha to about 1500 g ai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 g ae/ha to about 300 g ae/ha. In some embodiments, the isoproturon or sait thereof is applied at a rate from about 375 g ai/ha to about 1500 g ai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2.5 g ae/ha to about 10 g ae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and isoproturon or sait thereof for the control of AMARE, SINAR, GALAP, LAMPU or VERPE.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or sait or ester thereof is used in combination with linuron or sait thereof. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to linuron or sait thereof is within the range from about 1:2250 to about 6:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to linuron or sait thereof is within the range from about 1:39 to about 1:19. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to linuron or sait thereof is within the range from about 1:1364 to about 1:1. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and linuron or sait thereof. 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 from about 52 grams active ingrédient per hectare (g ai/ha) to about 4800 g ai/ha based on the total amount of active ingrédients in the composition. In certain embodiments, the composition is applied at an application rate from about 53 grams active ingrédient per hectare (g ai/ha) to about 3050 g ai/ha based on the total amount of active ingrédients in the composition. In some embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation with a compound of formula (I) or sait or ester thereof and linuron or sait thereof, e.g., sequentially or simultaneously. In some embodiments, the linuron or sait thereof is applied at a rate from about 50 g ai/ha to about 4500 g ai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 g ae/ha to about 300 g ae/ha. In some embodiments, the linuron or sait thereof is applied at a rate from about 50 g ai/ha to about 620 g ai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 16 g ae/ha to about 32 g ae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and linuron or sait thereof for the control of BRAPP.
-48In certain embodiments of the compositions and methods described herein, the compound of formula (I) or sait or ester thereof is used in combination with methibenzuron or sait thereof. With regard to the compositions, in some embodiments, the weight ratio ofthe compound of formula (I) or sait or ester thereof to methibenzuron or sait thereof is within the range from about 1:1400 to about 4:1. In certain embodiments, the weight ratio ofthe compound of formula (I) or sait or ester thereof to methibenzuron or sait thereof is within the range from about 1:909 to about 1:1. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and methibenzuron or sait thereof. 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 from about 72 grams active ingrédient per hectare (g ai/ha) to about 3100 g ai/ha based on the total amount of active ingrédients in the composition. In certain embodiments, the composition is applied at an application rate from about 73 grams active ingrédient per hectare (g ai/ha) to about 2050 g ai/ha based on the total amount of active ingrédients in the composition. In some embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation with a compound of formula (I) or sait or ester thereof and methibenzuron or sait thereof, e.g., sequentially or simultaneously. In some embodiments, the methibenzuron or sait thereof is applied at a rate from about 70 g ai/ha to about 2800 g ai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 g ae/ha to about 300 g ae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and methibenzuron or sait thereof.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or sait or ester thereof is used in combination with metribuzin or sait thereof. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to metribuzin or sait thereof is within the range from about 1:2800 to about 6:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to metribuzin or sait thereof is within the range from about 1:509 to about 1:1. In certain embodiments, the weight ratio ofthe compound of formula (I) or sait or ester thereof to metribuzin or sait thereof is within the range from about 1:168 to about 1:1. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and metribuzin or sait thereof. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable végétation or locus thereof or
-49applying 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 from about 52 grams active ingrédient per hectare (g ai/ha) to about 5900 g ai/ha based on the total amount of active ingrédients in the composition. In certain embodiments, the composition is applied at an application rate from about 55 grams active ingrédient per hectare (g ai/ha) to about 2300 g ai/ha based on the total amount of active ingrédients in the composition. In some embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation with a compound of formula (I) or sait or ester thereof and metribuzin or sait thereof, e.g., sequentially or simultaneously. In some embodiments, the metribuzin or sait thereof is applied at a rate from about 50 g ai/ha to about 5600 g ai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 g ae/ha to about 300 g ae/ha. In some embodiments, the metribuzin or sait thereof is applied at a rate from about 25 g ai/ha to about 420 g ai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2.5 g ae/ha to about 32 g ae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and metribuzin or sait thereof for the control of SETFA, KCHSC, LAMPU, SASKR, CHEAL or SINAR.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or sait or ester thereof is used in combination with propanil or sait thereof. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to propanil or sait thereof is within the range from about 1:2800 to about 1:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to propanil or sait thereof is within the range from about 1:767 to about 1:12. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to propanil or sait thereof is within the range from about 1:772 to about 1:12. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to propanil or sait thereof is within the range from about 1:384 to about 1:24. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl or n-butyl ester and propanil. In one embodiment, the composition comprises the compound of formula (I) and propanil, wherein the weight ratio of the compound of formula (I) to propanil is about 1:384 to about 1:48. In one embodiment, the composition comprises the compound of formula (I) and propanil, wherein the weight ratio of the compound of formula (I) to propanil is about 1:384 to about 1:48. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and propanil, wherein the weight ratio of the benzyl
-50ester of the compound of formula (I) to propanil is about 1:767 to about 1:24. In one embodiment, the composition comprises the π-butyl ester of the compound of formula (I) and propanil, wherein the weight ratio of the n-butyl ester of the compound of formula (I) to propanil is about 1:210. 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 from about 422 grams active ingrédient per hectare (g ai/ha) to about 5900 g ai/ha based on the total amount of active ingrédients in the composition. In certain embodiments, the composition is applied at an application rate from about 425 grams active ingrédient per hectare (g ai/ha) to about 3400 g ai/ha based on the total amount of active ingrédients in the composition. In some embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation with a compound of formula (I) or sait or ester thereof and propanil or sait thereof, e.g., sequentially or simultaneously. In some embodiments, the propanil or sait thereof is applied at a rate from about 420 g ai/ha to about 5600 g ai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 g ae/ha to about 300 g ae/ha. In some embodiments, the propanil or sait thereof is applied at a rate from about 210g ai/ha to about 6720 g ai/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 (g ae/ha) to about 70 g ae/ha. In some embodiments, the propanil or sait thereof is applied at a rate from about 420 g ai/ha to about 3360 g ai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 4 g acid équivalent per hectare (g ae/ha) to about 35 g ae/ha. In some embodiments, the propanil or sait thereof is applied at a rate from about 420 g ai/ha to about 3360 g ai/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 (g ae/ha) to about 35 g ae/ha. In certain embodiments, the methods utilize the compound of formula (I), or its benzyl or n-butyl ester and propanil. In one embodiment, the methods utilize the compound of formula (I) and propanil, wherein the compound of formula (I) is applied at a rate from about 4.38 g acid équivalent per hectare (g ae/ha) to about 35 g ae/ha, and propanil is applied at a rate of about 420 g ai/ha to about 3360 g ai/ha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and propanil, wherein the benzyl ester of the compound of formula (I) is applied at a rate from about 4.38 g acid équivalent per hectare (g ae/ha) to about 35 g ae/ha, and propanil is applied at a rate of about 420 g ai/ha to about 3360 g ai/ha. In one embodiment, the methods utilize the n-butyl ester ofthe compound of formula (I) and propanil, wherein the n-butyl ester of the compound of formula (I) is applied
-51 at a rate of about 16 g acid équivalent per hectare (g ae/ha), and propanil is applied at a rate of about 3360 g ai/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or sait or ester thereof in combination with propanil are used to control ECHCG, ECHCO, COMBE, IPOHE, or SCPMA.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or sait or ester thereof is used in combination with pyridate. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to pyridate is within the range from about 1:800 to about 12:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to pyridate is within the range from about 1:545 to about 6:1. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and pyridate. 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 from about 27 grams active ingrédient per hectare (g ai/ha) to about 1800 g ai/ha based on the total amount of active ingrédients in the composition. In certain embodiments, the composition is applied at an application rate from about 28 grams active ingrédient per hectare (g ai/ha) to about 1350 g ai/ha based on the total amount of active ingrédients in the composition. In some embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation with a compound of formula (I) or sait or ester thereof and pyridate, e.g., sequentially or simultaneously. In some embodiments, the pyridate is applied at a rate from about 25 g ai/ha to about 1600 g ai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 g ae/ha to about 300 g ae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and pyridate.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or sait or ester thereof is used in combination with siduron or sait thereof. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to siduron or sait thereof is within the range from about 1:4500 to about 2:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to siduron or sait thereof is within the range from about 1:2728 to about 1:3. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and siduron or sait thereof. With respect to the methods, in certain
-52embodiments, 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 from about 142 grams active ingrédient per hectare (g ai/ha) to about 9300 g ai/ha based on the total amount of active ingrédients in the composition. In certain embodiments, the composition is applied at an application rate from about 143 grams active ingrédient per hectare (g ai/ha) to about 6050 g ai/ha based on the total amount of active ingrédients in the composition. In some embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation with a compound of formula (I) or sait or ester thereof and siduron or sait thereof, e.g., sequentially or simultaneously. In some embodiments, the siduron or sait thereof is applied at a rate from about 140 g ai/ha to about 9000 g ai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 g ae/ha to about 300 g ae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and siduron or sait thereof.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or sait or ester thereof is used in combination with simazine or sait thereof. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to simazine or sait thereof is within the range from about 1:4250 to about 2:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to simazine or sait thereof is within the range from about 1:2728 to about 1:3. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to simazine or sait thereof is within the range from about 1:280 to about 1:17.5. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and simazine or sait thereof. 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 from about 142 grams active ingrédient per hectare (g ai/ha) to about 8800 g ai/ha based on the total amount of active ingrédients in the composition. In certain embodiments, the composition is applied at an application rate from about 143 grams active ingrédient per hectare (g ai/ha) to about 6050 g ai/ha based on the total amount of active ingrédients in the composition. In certain embodiments, the composition is applied at an application rate from about 568 grams active ingrédient per hectare (g ai/ha) to about 2272 g ai/ha based on the total amount of active ingrédients in the composition. In some embodiments, the methods comprise contacting the
-53undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation with a compound of formula (I) or sait or ester thereof and simazine or sait thereof, e.g., sequentially or simultaneously. In some embodiments, the simazine or sait thereof is applied at a rate from about 140 g ai/ha to about 8500 g ai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 g ae/ha to about 300 g ae/ha. In some embodiments, the simazine or sait thereof is applied at a rate from about 560 g ai/ha to about 2240 g ai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 8 g ae/ha to about 32 g ae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and simazine or sait thereof for the controi of BRAPP, ECHCG, ECHCO, CYPIR or XANST.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or sait or ester thereof is used in combination with simetryne or sait thereof. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to simetryne or sait thereof is within the range from about 1:1000 to about 12:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to simetryne or sait thereof is within the range from about 1:682 to about 6:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to simetryne or sait thereof is within the range from about 1:56 to about 1:3.5. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and simetryne or sait thereof. 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 from about 27 grams active ingrédient per hectare (g ai/ha) to about 2300 g ai/ha based on the total amount of active ingrédients in the composition. In certain embodiments, the composition is applied at an application rate from about 28 grams active ingrédient per hectare (g ai/ha) to about 1650 g ai/ha based on the total amount of active ingrédients in the composition. In some embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation with a compound of formula (I) or sait or ester thereof and simetryne or sait thereof, e.g., sequentially or simultaneously. In some embodiments, the simetryne or sait thereof is applied at a rate from about 25 g ai/ha to about 2000 g ai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 g ae/ha to about 300 g ae/ha. In some embodiments, the simetryne or sait thereof is applied at a rate from about 110 g ai/ha to about 450 g ai/ha and the compound
-54of formula (I) of sait or ester thereof is applied at a rate from about 8 g ae/ha to about 32 g ae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and simetryne or sait thereof for the control of ECHCO, ECHOR, CYPIR, CYPRO, FIMMI orLEFCH.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or sait or ester thereof is used in combination with tebuthiuron or sait thereof. With regard to the compositions, in some embodiments, the weight ratio ofthe compound of formula (I) or sait or ester thereof to tebuthiuron or sait thereof is within the range from about 1:2240 to about 2:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to tebuthiuron or sait thereof is within the range from about 1:1818 to about 1:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to tebuthiuron or sait thereof is within the range from about 1:420 to about 1:6.5. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and tebuthiuron or sait thereof. 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 from about 142 grams active ingrédient per hectare (g ai/ha) to about 4780 g ai/ha based on the total amount of active ingrédients in the composition. In certain embodiments, the composition is applied at an application rate from about 143 grams active ingrédient per hectare (g ai/ha) to about 4100 g ai/ha based on the total amount of active ingrédients in the composition. In some embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation with a compound of formula (I) or sait or ester thereof and tebuthiuron or sait thereof, e.g., sequentialiy or simultaneously. In some embodiments, the tebuthiuron or sait thereof is applied at a rate from about 140 g ai/ha to about 4480 g ai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 g ae/ha to about 300 g ae/ha. In some embodiments, the tebuthiuron or sait thereof is applied at a rate from about 140 g ai/ha to about 3360 g ai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 4 g ae/ha to about 32 g ae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and tebuthiuron or sait thereof for the control of BRSNN, CIRAR, CYPES, ECHCG, IPOHE, orXANST.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or sait or ester thereof is used in combination with terbuthylazine or
-55salt thereof. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to terbuthylazine or sait thereof is within the range from about 1:1500 to about 3:1. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to terbuthylazine or sait thereof is within the range from about 1:1018 to about 1:2.5. In certain embodiments, the weight ratio of the compound of formula (I) or sait or ester thereof to terbuthylazine or sait thereof is within the range from about 1:62 to about 1:31. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and terbuthylazine or sait thereof. 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 from about 127 grams active ingrédient per hectare (g ai/ha) to about 3300 g ai/ha based on the total amount of active ingrédients in the composition. In certain embodiments, the composition is applied at an application rate from about 128 grams active ingrédient per hectare (g ai/ha) to about 2290 g ai/ha based on the total amount of active ingrédients in the composition. In some embodiments, the methods comprise contacting the undesirable végétation or locus thereof or applying to the soil or water to prevent the emergence or growth of végétation with a compound of formula (I) or sait or ester thereof and terbuthylazine or sait thereof, e.g., sequentially or simultaneously. In some embodiments, the terbuthylazine or sait thereof is applied at a rate from about 125 g ai/ha to about 3000 g ai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 2 g ae/ha to about 300 g ae/ha. In some embodiments, the terbuthylazine or sait thereof is applied at a rate from about 125 g ai/ha to about 1000 g ai/ha and the compound of formula (I) of sait or ester thereof is applied at a rate from about 16g ae/ha to about 32 g ae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and terbuthylazine or sait thereof for the control of XANST.
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; 2,417280
-56D choline sait, 2,4-D esters and amines, 2,4-DB; 3,4-DA; 3,4-DB; 2,4-DEB; 2,4-DEP; 3,4-DP; 2,3,6-TBA; 2,4,5-T; 2,4,5-TB; acetochlor, acifluorfen, aclonifen, acrolein, alachlor, allidochlor, alloxydim, allyl alcohol, alorac, ametridione, ametryn, amibuzin, amicarbazone, amidosulfuron, aminocyclopyrachlor, aminopyralid, amiprofos-methyl, amitrole, ammonium sulfamate, anilofos, anisuron, asulam, atraton, azafenidin, azimsulfuron, aziprotryne, barban, BCPC, beflubutamid, benazolin, bencarbazone, benfluralin, benfuresate, bensulfuron-methyl, bensulide, benthiocarb, benzadox, benzfendizone, benzipram, benzobicyclon, benzofenap, benzofluor, benzoylprop, benzthiazuron, bialaphos, bicyclopyrone, bifenox, bilanafos, bispyribac-sodium, borax, bromacil, bromobonil, bromobutide, bromofenoxim, 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, 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, cyclopyrimorate, cycloate, cyclosulfamuron, cycloxydim, cycluron, cyhalofop-butyl, cyperquat, cyprazine, cyprazole, cypromid, daimuron, dalapon, dazomet, delachlor, desmedipham, desmetryn, diallate, dicamba, dichlobenil, dichloralurea, dichlormate, dichlorprop, dichlorprop-P, diclofopmethyl, diclosulam, diethamquat, diethatyl, difenopenten, difenoxuron, difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimexano, dimidazon, dinitramine, dinofenate, dinoprop, dinosam, dinoseb, dinoterb, diphenamid, dipropetryn, diquat, disul, dithiopyr, DMP A, DNOC, DSMA, EBEP, eglinazine, endothal, epronaz, EPTC, erbon, esprocarb, ethalfluralin, ethbenzamide, ethametsulfuron, ethidimuron, ethiolate, ethobenzamid, etobenzamid, ethofumesate, ethoxyfen, ethoxysulfuron, etinofen, etnipromid, etobenzanid, EXD, fenasulam, fenoprop, fenoxaprop, fenoxaprop-P-ethyl, fenoxaprop-P-ethyl + isoxadifen-ethyl, fenoxasulfone, fenteracol, fenthiaprop, fentrazamide, fenuron, ferrous sulfate, flamprop, flamprop-M, flazasulfuron, florasulam, fluazifop, fluazifop-P-butyl, fluazolate, flucarbazone, flucetosulfuron, fluchloralin, flufenacet, flufenican, flufenpyr-ethyl, flumetsulam, flumezin, flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, fluoromidine, fluoronitrofen, fluothiuron, flupoxam, flupropacil, flupropanate, flupyrsulfuron,
-57fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fomesafen, foramsulfuron, fosamine, fumiclorac, fiiryloxyfen, glufosinate, glufosinate-ammonium, glufosinate-P-ammonium, glyphosate, halauxifen, halauxifen-methyl, halosafen, halosulfuronmethyl, haloxydine, haloxyfop-methyl, haloxyfop-P-methyl, hexachloroacetone, hexaflurate, imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazosulfuron, imazethapyr, indanofan, indaziflam, iodobonil, iodomethane, iodosulfuron, iodosulfuron-ethyl-sodium, iofensulfuron, ipazine, ipfencarbazone, iprymidam, isocarbamid, isocil, isomethiozin, isonoruron, isopolinate, isopropalin, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, karbutilate, ketospiradox, lactofen, lenacil, MAA, ΜΑΜΑ, MCPA esters and amines, MCPA-thioethyl, MCPB, mecoprop, mecoprop-P, medinoterb, mefenacet, mefluidide, mesoprazine, mesosulfiiron, 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, metsulfiiron, metsulfuron-methyl, molinate, monalide, monisouron, monochloroacetic acid, monolinuron, monuron, morfamquat, MSMA, naproanilide, napropamide, naptalam, neburon, nicosulfuron, nipyraclofen, nitralin, nitrofen, nitrofluorfen, norflurazon, noruron, OCH, orbencarb, or/Ao-dichlorobenzene, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxapyrazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraflufen-ethyl, parafluron, paraquat, pebulate, pelargonic acid, pendimethalin, penoxsulam, pentachlorophenol, pentanochlor, pentoxazone, perfluidone, pethoxamid, phenisopham, phenmedipham, phenmedipham-ethyl, phenobenzuron, phenylmercury acetate, picloram, picolinafen, pinoxaden, piperophos, potassium arsenite, potassium azide, potassium cyanate, pretilachlor, primisulfuron-methyl, procyazine, prodiamine, profluazol, profluralin, profoxydim, proglinazine, prohexadionecalcium, prometon, prometryn, pronamide, propachlor, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propyrisulfuron, propyzamide, prosulfalin, prosulfocarb, prosulfuron, proxan, prynachlor, pydanon, pyraclonil, pyraflufen-ethyl, pyrasulfotole, pyrazogyl, pyrazolynate, pyrazosulfuron-ethyl, pyrazoxyfen, pyribenzoxim, pyributicarb, pyriclor, pyridafol, pyriftalid, pyriminobac, pyrimisulfan, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quinonamid, quizalofop, quizalofop-P-ethyl, rhodethanil, rimsulfuron, saflufenacil, S-metolachlor, sebuthylazine, secbumeton, sethoxydim, simeton, SMA, sodium arsenite, sodium azide, sodium chlorate, sulcotrione, sulfallate, sulfentrazone, sulfometuron, sulfosate, sulfosulfuron, sulfuric acid, sulglycapin, swep, SYN-523, TCA, tebutam, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbuchlor,
-58terbumeton, terbutryn, tetrafluron, thenylchlor, thiazafluron, thiazopyr, thidiazimin, thidiazuron, thiencarbazone-methyl, thifensulfuron, thifensulfum-methyl, thiobencarb, tiocarbazil, tioclorim, topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron, tribenuronmethyl, tricamba, triclopyr choline sait, triclopyr esters and salts, tridiphane, trietazine, trifloxysulfuron, trifluralin, triflusulfuron, trifop, trifopsime, trihydroxytriazine, trimeturon, tripropindan, tritac tritosulfuron, vemolate, xylachlor and salts, esters, optically active isomers and mixtures thereof.
The compositions and methods described herein, can further be used in conjunction with glyphosate, 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, glufosinate, glutamine synthetase inhibitors, dicamba, phenoxy auxins, pyridyloxy auxins, synthetic auxins, auxin transport inhibitors, aryloxyphenoxypropionates, cyclohexanediones, phenylpyrazolines, acetyl CoA carboxylase (ACCase) inhibitors, imidazolinones, sulfonylureas, pyrimidinylthiobenzoates, triazolopyrimidines, sulfonylaminocarbonyltriazolinones, acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors, 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, phytoene desaturase inhibitors, carotenoid biosynthesis inhibitors, protoporphyrinogen oxidase (PPO) inhibitors, cellulose biosynthesis inhibitors, mitosis inhibitors, microtubule inhibitors, very long chain fatty acid inhibitors, fatty acid and lipid biosynthesis inhibitors, photosystem I inhibitors, photosystem II inhibitors, triazines, and bromoxynil on glyphosate-tolerant, EPSP synthase inhibitor-tolerant, glufosinate-tolerant, glutamine synthetase inhibitor-tolerant, dicamba-tolerant, phenoxy auxin-tolerant, pyridyloxy auxin-tolerant, auxin-tolerant, auxin transport inhibitor-tolerant, aryloxyphenoxypropionatetolerant, cyclohexanedione-tolerant, phenylpyrazoline-tolerant, ACCase-tolerant, imidazolinonetolerant, sulfonylurea-tolerant, pyrimidinylthiobenzoate-tolerant, triazolopyrimidine-tolerant, sulfonylaminocarbonyltriazolinone-tolerant, ALS- or AHAS-tolerant, HPPD-tolerant, phytoene desaturase inhibitor-tolerant, carotenoid biosynthesis inhibitor tolérant, PPO-tolerant, cellulose biosynthesis inhibitor-tolerant, mitosis inhibitor-tolerant, microtubule inhibitor-tolerant, very long chain fatty acid inhibitor-tolerant, fatty acid and lipid biosynthesis inhibitor-tolerant, photosystem I inhibitor-tolerant, photosystem II inhibitor-tolerant, triazine-tolerant, and bromoxynil-tolerant crops, 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
-59described 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 Ύ-phenyl-sulfonylbenzoic acid amides, to enhance their selectivity. In some embodiments, the safeners are employed in rice, cereal, corn, or maize settings. In some embodiments, the safener is cloquintocet or an ester or sait thereof. In certain embodiments, cloquintocet is utilized to antagonize harmful effects of the compositions on rice and cereals. In some embodiments, the safener is cloquintocet (mexyl).
In some embodiments, the compositions described herein are employed in combination with one or more plant growth regulators, such as 2,3,5-tri-iodobenzoic acid, IAA, IB A, naphthaleneacetamide, α-naphthaleneacetic acids, benzyladenine, 4-hydroxyphenethyl alcohol, kinetin, zeatin, endothal, ethephon, pentachlorophenol, thidiazuron, tribufos, aviglycine, 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 (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 PSII 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 sélective weed control in the presence of crops, and should not react chemically with herbicidal components or other composition ingrédients. Such mixtures can be designed for application directly to weeds or their locus or can be concentrâtes or formulations
-60that are normally diluted with additional carriers and adjuvants before application. They can be solids, such as, for example, dusts, granules, water-dispersible granules, or wettable powders, or liquids, such as, for example, emulsifiable concentrâtes, solutions, émulsions or suspensions. They can also be provided as a pre-mix or tank mixed.
Suitable agricultural adjuvants and carriers include, but are not limited to, crop oil concentrate; nonylphenol ethoxylate; benzylcocoalkyldimethyl quatemary ammonium sait; blend of petroleum hydrocarbon, alkyl esters, organic acid, and anionic surfactant; C9-C11 alkylpolyglycoside; phosphated alcohol ethoxylate; natural primary alcohol (Cp-Ciô) ethoxylate; di-sec-butylphenol EO-PO block copolymer; polysiloxane-methyl cap; nonylphenol ethoxylate + urea ammonium nitrate; emulsified methylated seed oil; tridecyl alcohol (synthetic) ethoxylate (8EO); tallow amine ethoxylate (15 EO); PEG(400) dioleate-99.
Liquid carriers that can be employed include water and organic solvents. The organic solvents include, but are not limited to, petroleum fractions or hydrocarbons such as minerai oil, aromatic solvents, paraffinic oils, and the like; vegetable oils such as soÿbean 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 stéarate, n-butyl oleate, isopropyl myristate, propylene glycol dioleate, di-octyl succinate, di-butyl adipate, di-octyl phthalate and the like; esters of mono, di and polycarboxylic acids and the like. Spécifie organic solvents include, but are not limited to toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol monomethyl ether and diethylene glycol monomethyl ether, methyl alcohol, ethyl alcohol, isopropyl alcohol, amyl alcohol, ethylene glycol, propylene glycol, glycérine, 7V-methyl-2pyrrolidinone, jV./V-dimethyl alkylamides, dimethyl sulfoxide, liquid fertilizers and the like. In certain embodiments, water is the carrier for the dilution of concentrâtes.
Suitable solid carriers include but are not limited to talc, pyrophyllite clay, silica, attapulgus clay, kaolin clay, kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, Fuller's earth, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, lignin, cellulose, and the like.
In some embodiments, the compositions described herein further comprise one or more surface-active agents. In some embodiments, such surface-active agents are employed in both solid and liquid compositions, and in certain embodiments those designed to be diluted with carrier before application. The surface-active agents can be anionic, cationic or nonionic in
-61 character and can be empioyed as emulsifying agents, wetting agents, suspending agents, or for other purposes. Surfactants which may also be used in the présent formulations are described, inter alia, in “McCutcheon’s Détergents and Emulsifiers Annual,” MC Publishing Corp., Ridgewood, New Jersey, 1998 and in “Encyclopedia of Surfactants,” Vol. I-III, Chemical Publishing Co., New York, 1980-81. Surface-active agents include, but are not limited to salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide additionproducts, such as nonylphenol-Cig ethoxylate; alcohol-alkylene oxide addition products, such as tridecyl alcoholCi6 ethoxylate; soaps, such as sodium stéarate; alkylnaphthalene-sulfonate salts, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl) sulfosuccinate; sorbitol esters, such as sorbitol oleate; quatemary amines, such as lauryl trimethylammonium chloride; polyethylene glycol esters of fatty acids, such as polyethylene glycol stéarate; block copolymers of ethylene oxide and propylene oxide; salts of mono and dialkyl phosphate esters; vegetable or seed oils such as soybean oil, rapeseed/canola oil, olive oil, castor oil, sunflower seed oil, coconut oil, com oil, cottonseed oil, linseed oil, palm oil, peanut oil, safïlower oil, sesame oil, tung oil and the like; and esters of the above vegetable oils, and in certain embodiments, methyl esters.
In some embodiments, these materials, such as vegetable or seed oils and their esters, can be used interchangeably as an agricultural adjuvant, as a liquid carrier or as a surface active agent.
Other exemplary additives for use in the compositions provided herein include but are not limited to compatibilizing agents, antifoam agents, sequestering agents, neutralizing agents and buffers, corrosion inhibitors, dyes, odorants, spreading agents, pénétration aids, sticking agents, dispersing agents, thickening agents, freezing point depressants, antimicrobial agents, and the like. The compositions may also contain other compatible components, for example, other herbicides, plant growth régulants, fongicides, insecticides, and the like and can be formulated with liquid fertilizers or solid, particulate fertilizer carriers such as ammonium nitrate, urea and the like.
In some embodiments, the concentration of the active ingrédients in the compositions described herein is from 0.0005 to 98 percent by weight. In some embodiments, the concentration is from 0.0006 to 90 percent by weight. In compositions designed to be empioyed as concentrâtes, the active ingrédients, in certain embodiments, are présent in a concentration from 0.1 to 98 weight percent, and in certain embodiments 0.2 to 90 weight percent. Such compositions are, in certain embodiments, diluted with an inert carrier, such as water, before
-62application. The diluted compositions usually appiied to weeds or the locus of weeds contain, in certain embodiments, 0.0052 to 25.0 weight percent active ingrédient and in certain embodiments contain 0.01 to 15 weight percent active ingrédient.
The présent compositions can be appiied to weeds or their locus by the use of conventional ground or aerial dusters, sprayers, and granule applicators, by addition to irrigation or paddy water, and by other conventional means known to those skilled in the art.
The described embodiments and following examples are for illustrative purposes and are not intended to limit the scope of the claims. Other modifications, uses, or combinations with respect to the compositions described herein will be apparent to a person of ordinary skill in the art without departing from the spirit and scope of the claimed subject matter.
Examples Results in Examples I, II, III, IV, and V are greenhouse trial results. Exampie 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 appiied. 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 appiied in the irrigation solution as needed and water was added on a regular basis. Supplémentai lighting was provided with overhead métal halide 1000-Watt lamps as necessary. The plants were employed for testing when they reached the first through fourth true leaf stage.
Treatments consisted of the acid or esters of 4-amino-3-chloro-5-fluoro-6-(4-chloro-2fluoro-3-methoxy-phenyl) pyridine-2-carboxylic acid (Compound A), each formulated as an SC (suspension concentrate), and various herbicidal components alone and in combination. Forms of compound A were appiied on an acid équivalent basis.
-63Forms of compound A (compound of formula I) tested include:
Compound A Acid
Compound A n-Butyl Ester
Compound A Benzyl Ester
Other herbicidal components were applied on an active ingrédient basis and included Photosystem II (PSII)-inhibiting herbicides propanil formulated as Stam® M4 EC, bentazon10 sodium formulated as Basagran®, atrazine formulated as Atrazine 90 WDG, bromoxynil octanoate ester formulated as Buctril®, simetryne (technical grade material), simazine formulated as Princep® Caliber 90, ioxynil (technical grade material), cyanazine (technical grade material), and hexazinone (technical grade material).
Treatment requirements were calculated based upon the rates being tested, the concentration of active ingrédient or acid équivalent in the formulation, and a 12 mL application volume at a rate of 187 L/ha.
-64For treatments comprised of formulated compounds, measured amounts of compounds were placed individually in 25 mL glass vials and diluted in a volume of 1.25% (v/v) Agri-Dex® crop oil concentrated to obtain 12X stock solutions. If a test compound did not dissolve readily, the mixture was warmed and/or sonicated. Application solutions were prepared by adding an appropriate amount of each stock solution (e.g., 1 mL) and diluted to the appropriate final concentrations with the addition of 10 mL of an aqueous mixture of 1.25% (v/v) crop oil concentrate so that the final spray solutions contained 1.25+/-0.05% (v/v) crop oil concentrate.
For treatments comprised of technical compounds, weighed amounts can be placed individually in 25 mL glass vials and dissolved in a volume of 97:3 v/v acetone/DMSO to obtain 12X stock solutions. If a test compound does not dissolve readily, the mixture can be warmed and/or sonicated. Application solutions can be prepared by adding an appropriate amount of each stock solution (e.g., 1 mL) and diluted to the appropriate final concentrations with the addition of 10 mL of an aqueous mixture of 1.5% (v/v) crop oil concentrate so that the final spray solutions contain 1.25% (v/v) crop oil concentrate. When technical materials are used, the concentrated stock solutions can be added to the spray solutions so that the final acetone and DMSO concentrations of the application solutions are 16.2% and 0.5%, respectively.
For treatments comprised of formulated and technical compounds, weighed amounts of the technical materials were placed individually in 25 mL glass vials and dissolved in a volume of 97:3 v/v acetone/DMSO to obtain 12X stock solutions, and measured amounts of the formulated compounds were placed individually in 25 mL glass vials and diluted in a volume of 1.5% (v/v) crop oil concentrate or water to obtain 12X stock solutions. If a test compound did not dissolve readily, the mixture was warmed and/or sonicated. Application solutions were prepared by adding an appropriate amount of each stock solution (eg, 1 mL) and diluted to the appropriate final concentrations with the addition of an appropriate amount of an aqueous mixture of 1.5% (v/v) crop oil concentrate so that the final spray solutions contained 1.25% (v/v) crop oil concentrate. As required, additional water and/or 97:3 v/v acetone/DMSO was added to individual application solutions so that the final acetone and DMSO concentrations of the application solutions being compared were 8.1% and 0.25%, respectively.
Ail stock solutions and applications solutions were visually inspected for compound compatibility prior to application. Spray solutions were applied to the plant material with an overhead Mandel track sprayer equipped with a 8002E nozzles calibrated to deliver 187 L/ha over an application area of 0.503 m2 at a spray height of 18 to 20 inches (46 to 50 cm) above average plant canopy height. Control plants were sprayed in the same manner with the solvent blank.
-65The 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 and 100 corresponds to complété kill.
Colby’s équation was used to détermine the herbicidal effects expected from the mixtures (Colby, S.R. 1967. Calculation ofthe synergistic and antagonistic response ofherbicide combinations. Weeds 15:20-22.).
The following équation was used to calculate the expected activity of mixtures containîng two active ingrédients, A and B:
Expected = A + B - (A x B/100)
A = observed efficacy of active ingrédient A at the same concentration as used in the mixture.
B = observed efficacy of active ingrédient B at the same concentration as used in the mixture.
The compounds tested, application rates employed, plant species tested, and results are given in Tables 1-14.
Table 1. Synergistic Activity of Foliar-Applied Compound A Acid and Propanil Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound A Acid Propanil Visual Weed Control (%) - 21 DAA
ECHCG ECHCO IPOHE
gae/ha gai/ha Obs Exp Obs Exp Obs Exp
4.38 0 33 43 - 15 -
8.75 0 55 63 - 35 -
0 420 10 10 - 0 -
0 840 10 25 - 0 -
0 1680 40 25 - 0 -
4.38 420 90 39 75 48 25 15
8.75 420 95 60 85 66 50 35
4.38 840 90 39 75 57 50 15
8.75 840 95 60 90 72 65 35
4.38 1680 95 60 90 57 60 15
8.75 1680 95 73 100 72 55 35
Compound A Acid Propanil Visual Weed Control (%) - 20
DAA
IPOHE
gae/ha gai/ha Obs Exp
19.4 0 15 -
0 3360 40 -
19.4 3360 73 49
Table 2. Synergistic Activity ofFoliar-Applied Compound A Benzyl Ester and Propanil Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound A Benzyl Ester Propanil Visual Weed Control (%) - 21 DAA
ECHCG ECHCO IPOHE
gae/ha gai/ha Obs Exp Obs Exp Obs Exp
4.38 0 48 - 60 0
8.75 0 55 - 68 15
17.5 0 85 - 83 38
0 420 10 - 10 0
0 840 10 - 25 0
0 1680 40 - 25 0
4.38 420 60 53 75 64 15 0
8.75 420 90 60 90 71 50 15
17.5 420 95 87 95 84 60 38
4.38 840 90 53 85 70 20 0
8.75 840 95 60 80 76 35 15
17.5 840 95 87 99 87 65 38
4.38 1680 70 69 100 70 50 0
8.75 1680 90 73 100 76 50 15
17.5 1680 95 91 100 87 65 38
Compound A Benzyl Ester Propanil Visual Weed Control (%) - 20 DAA
IPOHE
gae/ha gai/ha Obs Exp
16 0 18 -
0 3360 40 -
16 · 3360 85 51
Compound A Benzyl Ester Propanil Visual Weed Control (%) - 20 DAA
COMBE
gae/ha g ai/ha Obs Exp
6 0 80 -
24 0 0 -
0 3360 10 -
6 3360 80 80
24 3360 95 82
Table 3. Synergistic Activity of Foliar-Applied Compound A η-Butyl Ester and Propanil Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound A n-Butyl Ester Propanil Visual Weed Control (%) - 20 DAA
IPOHE
gae/ha gai/ha Obs Exp
16 0 15 -
0 3360 40 -
16 3360 70 49
Table 4. Synergistic Activity of Foliar-Applied Compound A Acid and Bentazon-sodium Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound A Acid Bentazonsodium Visual Weed Control (%) - 21 DAA
IPOHE
gae/ha gai/ha Obs Exp
4.38 0 15 -
0 105 0 -
0 210 0 -
0 420 10 -
4.38 105 30 15
4.38 210 60 15
4.38 420 50 24
Compound A Acid Bentazonsodium Visual Weed Control (%) - 20 DAA
IPOHE
gae/ha gaeha Obs Exp
21.2 0 35 -
42.4 0 55 -
0 840 13 -
21.2 840 73 43
42.4 840 80 61
Table 5. Synergistic Activity ofFoliar-Applied Compound A Benzyl Ester and Bentazon-sodium Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound A Benzyl Ester Bentazonsodium Visual Weed Control (%) - 21 DAA
IPOHE
g ae/ha gai/ha Obs Exp
4.38 0 0
8.75 0 15
17.5 0 38
0 105 0
0 210 0
0 420 10
4.38 105 40 0
8.75 105 65 15
17.5 105 60 38
4.38 210 30 0
8.75 210 40 15
17.5 210 65 38
4.38 420 30 10
8.75 420 60 24
17.5 420 65 44
Compound A Benzyl Ester Bentazonsodium Visual Weed Control (%) - 20 DAA
IPOHE
gae/ha g aeha Obs Exp
17.5 0 38 -
35 0 55 -
0 840 13 -
17.5 840 60 45
35 840 78 61
Compound A Benzyl Ester Bentazon sodium Visual Weed Control (%) - 20 DAA
COMBE
g ae/ha gai/ha Obs Exp
6 0 70 -
24 0 80 -
0 280 10 -
6 280 75 73
24 280 95 82
Table 6. Synergistic Activity of Foliar-Applied Compound A n-Butyl Ester and Bentazonsodium Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound A n-Butyl Ester Bentazonsodium Visual Weed Control (%) - 20 DAA
IPOHE
gae/ha gaeha Obs Exp
17.5 0 48 -
0 840 13 -
17.5 840 85 54
Table 7. Synergistic Activity of Foliar-Applied Compound A Acid and Atrazine Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.
Compound A Acid Atrazine Visual Weed Control (%) - 22 DAA
BRAPP
gae/ha gai/ha Obs Exp
4.38 0 45 -
8.75 0 70 -
0 280 0 -
0 560 0 -
4.38 280 60 45
8.75 280 85 70
4.38 560 70 45
8.75 560 75 70
Compound A Acid Atrazine Visual Weed Control (%) - 22 DAA
ECHCG ECHCO CYPIR
gae/ha gai/ha Obs Exp Obs Exp Obs Exp
4.38 0 20 - 20 - 15 -
0 280 0 - 10 - 0 -
0 560 20 - 10 - 100 -
0 1120 70 - 60 - 80 -
4.38 280 50 20 50 28 100 15
4.38 560 80 36 70 28 100 100
4.38 1120 100 76 99 68 100 83
-71Table 8. Synergistic Activity ofFoliar-Applied Compound A Benzyl Ester and Atrazine Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.
Compound A Benzyl Ester Atrazine Visual Weed Control (%) - 22 DAA
BRAPP
gae/ha gai/ha Obs Exp
4.38 0 55
8.75 0 70
17.5 0 75
0 280 0
0 560 0
4.38 280 55 55
8.75 280 80 70
17.5 280 85 75
4.38 560 65 55
8.75 560 85 70
17.5 560 95 75
Table 9. Synergistic Activity ofFoliar-Applied Compound A Benzyl Ester and Bromoxynil
Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.
Compound A Benzyl Ester Bromoxynil Octanoate Ester Visual Weed Control (%) - 22 DAA
ECHCG
gae/ha gai/ha Obs Exp
8 0 35 -
16 0 65 -
32 0 80 -
0 140 0 -
8 140 50 35
16 140 80 65
32 140 90 80
Table 10. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Simetryne 10 Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.
Compound A Benzyl Ester Simetryne Visual Weed Control (%) - 21 DAA
ECHCO
gae/ha g ai/ha Obs Exp
8 0 75 -
16 0 85 -
32 0 95 -
0 450 45 -
8 450 100 86
16 450 95 92
32 450 100 97
Compound A Benzyl Ester Simetryne Visual Weed Control (%)-22 DAA
LEFCH
gae/ha gai/ha Obs Exp
8 0 35 -
16 0 40 -
0 225 40 -
8 225 80 61
16 225 70 64
Compound A Benzyl Ester Simetryne Visual Weed Control (%)-22DAA
CYPIR
gae/ha gai/ha Obs Exp
8 0 10
16 0 60
0 112.5 0
0 225 0
0 450 30
8 112.5 100 10
16 112.5 90 60
8 225 60 10
16 225 100 60
8 450 100 37
16 450 100 72
Table 11. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Simazine
Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.
Compound A Benzyl Ester Simazine Visual Weed Control (%) - 20 DAA
BRAPP ECHCG ECHCO CYPIR
gae/ha gai/ha Obs Exp Obs Exp Obs Exp Obs Exp
8 0 55 70 65 70
16 0 90 90 85 90
32 0 90 90 95 90
0 560 0 0 0 0
0 1120 0 0 0 0
0 2240 0 0 0 30
8 560 80 55 95 70 80 65 100 70
16 560 90 90 95 90 85 85 85 90
32 560 95 90 99 90 95 95 100 90
8 1120 80 55 85 70 75 65 100 70
16 1120 80 90 100 90 85 85 100 90
32 1120 95 90 99 90 95 95 100 90
8 2240 60 55 95 70 80 65 100 79
16 2240 95 90 95 90 90 85 100 93
32 2240 95 90 90 90 99 95 100 93
Table 12. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Cyanazine Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.
Compound A Benzyl Ester Cyanazine Visual Weed Control (%) - 20 DAA
IPOHE
gae/ha gai/ha Obs Exp
8 0 20 -
16 0 40 -
32 0 55 -
0 275 50 -
8 275 80 60
16 275 90 70
32 275 80 78
Table 13. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Ioxynil Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.
Compound A Benzyl Ester Ioxynil Visual Weed Control (%) - 20 DAA
IPOHE
gae/ha gai/ha Obs Exp
8 0 0 -
16 0 15 -
32 0 55 -
0 300 50 -
8 300 50 50
16 300 90 58
32 300 90 78
Table 14. Synergistic Activity ofFoliar-Applied Compound A Benzyl Ester and Hexazinone Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.
Compound A Benzyl Ester Hexazinone Visual Weed Control (%) - 21 DAA
ECHCO
gae/ha gai/ha Obs Exp
8 0 50
16 0 65
32 0 85
0 625 25
0 1250 55
8 625 100 63
16 625 100 74
32 625 100 89
8 1250 90 78
16 1250 100 84
32 1250 100 93
Compound A Benzyl Ester Hexazinone Visual Weed Control (%) - 21 DAA
ECHCG IPOHE
gae/ha gai/ha Obs Exp Obs Exp
8 0 45 - 10 -
16 0 85 - 25 -
32 0 90 - 60 -
0 625 20 - 80 -
8 625 85 56 90 82
16 625 90 88 99 85
32 625 90 92 100 92
BRAPP Brachiaria platyphylla (Griseb.) Nash signalgrass, broadleaf
COMBE Commelina benghalensis L. dayflower, Benghal
CYPIR Cyperus iria L. flatsedge, rice
10 CYPES Cyperus esculentus L. nutsedge, yellow
-75ECHCG Echinochloa crusgalli (L.) Beauv.
ECHCO Echinochloa colona (L.) Link
IPOHE Ipomoea hederacea Jacq.
LEFCH Leptochloa chinensis (L.) Nees g ae/ha = grams acid équivalent per hectare g ai/ha = grams active ingrédient per hectare Obs = observed value bamyardgrass junglerice momingglory, ivyleaf sprangletop, Chinese
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 dispensed in 365 mL aliquots into
Λ 16-ounce (oz.) non-perforated plastic pots with a surface area of 86.59 square centimeters (cm ) leaving a headspace of 3 centimeters (cm) in each pot Mud was allowed to dry 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 h photoperiod which was maintained at about 29°C during the day and 26°C during the night. Nutrients were added as Osmocote® (19:6:12, N:P:K + minor nutrients) at 2 g per 16-oz. pot and 4 g per 32-oz. pot. Water was added on a regular basis to maintain the paddy flood, and supplémentai lighting was provided with overhead métal halide 1000-Watt lamps as necessary. The plants were employed for testing when they reached the first through fourth true leaf stage.
Treatments consisted of the 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
-76(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 n-Butyl Ester
Compound A Benzyl Ester
Other herbicidal components were applied on an active ingrédient basis and included photosystem II (PSII)-inhibits propanil formulated as Stam® 4M EC bentazon-sodium formulated as Basagran®, and simetryne (technical grade material).
Treatment requirements for each compound or herbicidal component were calculated based upon the rates being tested, the concentration of active ingrédient or acid équivalent in the
-77formulation, 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 équivalent volume of an aqueous mixture containing 2.5% (v/v) crop oil concentrate so that the final application solutions contained 1.25% (v/v) crop oil concentrate.
Applications were made by injecting with a pipetter appropriate amounts of the application solutions, individually and sequentially, into the aqueous layer of the paddy. Control plants were treated in the same manner with the solvent blank. Applications were made so that ail treated plant material received the same concentrations of acetone and crop oil concentrate.
The treated plants and control plants were placed in a greenhouse as described above and water was added as needed to maintain a paddy flood. After approximately 3 weeks the condition of the test plants as compared with that of the untreated plants was determined visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury or growth inhibition and 100 corresponds to complété kill.
Colby’s équation was used to détermine the herbicidal effects expected from the mixtures (Colby, S.R. 1967. Calculation of the synergistic and antagonistic response of herbicide combinations. Weeds 15:20-22.).
The following équation was used to calculate the expected activity of mixtures containing two active ingrédients, A and B:
Expected = A + B - (A x B/100)
A = observed efficacy of active ingrédient A at the same concentration as used in the mixture.
B = observed efficacy of active ingrédient B at the same concentration as used in the mixture.
Some of the compounds tested, application rates employed, plant species tested, and results are given in Tables 15-20.
-78Table 15. Synergistic Activity of In-Water Applications of Compound À Acid and Propanil Herbicidal Compositions on Weed Controi in a Rice Cropping System.
Compound A Acid Propanil Visual Weed Controi (%) - 21 DAA
SCPMA
gae/ha g ai/ha Obs Exp
8.75 0 0
17.5 0 0
35 0 0
0 1680 50
0 3360 90
8.75 1680 50 50
17.5 1680 100 50
35 1680 100 50
8.75 3360 100 90
17.5 3360 100 90
35 3360 100 90
Table 16. Synergistic Activity of In-Water Applications of Compound A Benzyl Ester and Propanil Herbicidal Compositions on Weed Controi in a Rice Cropping System.
Compound A Benzyl Ester Propanil Visual Weed Controi (%) - 21 DAA
SCPMA
g ae/ha g ai/ha Obs Exp
8.75 0 0
17.5 0 0
35 0 0
0 1680 50
0 3360 90
8.75 1680 99 50
17.5 1680 100 50
35 1680 70 50
8.75 3360 100 90
17.5 3360 100 90
35 3360 100 90
Table 17. Synergistic Activity of In-Water Applications of Compound A Acid and Bentazonsodium Herbicidal Compositions on Weed Controi in a Rice Cropping System.
Compound A Acid Bentazonsodium Visual Weed Control (%) - 21 DAA
ECHCG LEFCH
gae/ha gae/ha Obs Exp Obs Exp
8.75 0 0 - 0 -
17.5 0 0 - 0 -
0 420 0 - 0 -
0 840 0 - 0 -
8.75 420 30 0 20 0
17.5 420 20 0 30 0
8.75 840 10 0 30 0
17.5 840 25 0 40 0
Compound A Acid Bentazonsodium Visual Weed Control (%) - 20 DAA
LEFCH SCPMA
gae/ha gae/ha Obs Exp Obs Exp
42.4 0 15 - 0 -
84.8 0 55 - 0 -
0 1120 0 - 0 -
42.4 1120 38 15 80 0
84.8 1120 63 55 100 0
Table 18. Synergistic Activity of In-Water Applications of Compound A Benzyl Ester and Bentazon-sodium Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound A Benzyl Ester Bentazonsodium Visual Weed Control (%) - 21 DAA
LEFCH
g ae/ha gae/ha Obs Exp
8.75 0 20 -
17.5 0 30 -
35 0 55 -
0 420 0 -
0 840 0 -
8.75 420 30 20
17.5 420 50 30
35 420 70 55
8.75 840 50 20
17.5 840 65 30
35 840 50 55
Compound A Benzyl Ester Bentazonsodium Visual Weed Control (%) - 20 DAA
LEFCH
gae/ha gae/ha Obs Exp
70 0 80 -
0 1120 0 -
70 1120 93 80
Compound A Benzyl Ester Bentazonsodium Visua Control Ό/ Weed (%) - 20
SCPMA
gae/ha gae/ha Obs Exp
35 0 0 -
70 0 0 -
0 1120 0 -
35 1120 100 0
70 1120 43 0
Table 19. Synergistic Activity of In-Water Applications of Compound A η-Butyl Ester and Bentazon-sodium Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound A η-Butyl Ester Bentazonsodium Visual Weed Control (%) - 20 DAA
ECHOR
gae/ha gae/ha Obs Exp
70 0 40 -
0 1120 0 -
70 1120 60 40
Compound A η-Butyl Ester Bentazonsodium Visual Weed Control (%) - 20 DAA
SCPMA
gae/ha gae/ha Obs Exp
35 0 0 -
70 0 0 -
0 1120 0 -
35 1120 100 0
70 1120 50 0
-81Table 20. Synergistic Activity of In-Water Applications of Compound A Benzyl Ester and Simetryne Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound A Benzyl Ester Simetryne Visual Weed Control (%) - 19 DAA
ECHOR FIMMI
gae/ha gai/ha Obs Exp Obs Exp
8 0 10 0
16 0 20 0
32 0 25 85
0 112.5 0 45
0 225 10 90
8 112.5 20 10 100 45
16 112.5 50 20 100 45
32 112.5 20 25 100 92
8 225 50 19 100 90
16 225 50 28 100 90
32 225 100 33 100 99
Compound A Benzyl Ester Simetryne Visual Weed Control (%) -19 DAA
CYPRO
gae/ha gai/ha Obs Exp
8 0 50
16 0 85
32 0 90
0 112.5 0
0 225 0
0 450 0
8 112.5 90 50
16 112.5 100 85
32 112.5 100 90
8 225 80 50
16 225 85 85
32 225 100 90
8 450 85 50
16 450 100 85
32 450 100 90
CYPRO
ECHCG
Cyperus rotundus L.
Echinochloa crusgalli (L.) Beauv.
nutsedge, purple bamyardgrass
-82ECHOR Echinochloa oryzoides (Ard.) Fritsch
FIMMI Fimbristylis miliacea (L.) Vahl
LEFCH Leptochloa chinensis (L.) Nees
SCPMA Schoenoplectus maritimus (L.) Lye g ae/ha = grams acid équivalent per hectare g ai/ha = grams active ingrédient per hectare Obs = observed value watergrass, early fringerush, globe sprangletop, Chinese clubrush, sea
Exp = expected value as calculated by Colby’s équation
DAA = days after application
Example III. Evaluation of Postemergence Herbicidal Activity of Mixtures in Cereal Crops in the Greenhouse.
Seeds of the desired test plant species were planted in Sun Gro MetroMix® 306 planting mixture, which typically has a pH of 6.0 to 6.8 and an organic matter content of about 30 percent, in plastic pots with a surface area of 103.2 square centimeters (cm2). When required to ensure good germination and healthy plants, a fongicide treatment and/or other chemical or physical treatment was applied. The plants were grown for 7-36 days in a greenhouse with an approximate 14 hour photoperiod which was maintained at about 18° C during the day and about 17° C during the night. Nutrients and water were added on a regular basis and supplémentai lighting was provided with overhead métal halide 1000-Watt lamps as necessary. The plants were 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-2fluoro-3-methoxy-phenyl)pyridine-2-carboxylic acid (Compound A), formulated as an SC, a second cereal herbicide alone and then both in combination.
Forms of compound A (compound of formula I) tested include:
Compound A Benzyl Ester
-83Other herbicidal components were applied on an active ingrédient basis and included PSII-inhibiting herbicides.
Measured aliquots of benzyl ester of 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3methoxy-phenyl)pyridine-2-carboxylic acid (Compound A) were placed in 25 milliliter (mL) glass vials and diluted in a volume of 1.25% (v/v) Agri-Dex® crop oil concentrate to obtain stock solutions. Compound requirements are based upon a 12 mL application volume at a rate of 187 liters per hectare (L/ha). Spray solutions of the second cereal herbicide and experimental compound mixtures were prepared by adding the stock solutions to the appropriate amount of dilution solution to form 12 mL spray solution with active ingrédients in two- and three-way combinations. Formulated compounds were applied to the plant material with an overhead Mandel track sprayer equipped with an 8002E nozzle calibrated to deliver 187 L/ha over an application area of 0.503 square meters (m2) at a spray height of 18 inches (46 cm) above average plant canopy. Control plants were sprayed in the same manner with the solvent blank.
The treated plants and control plants were placed in a greenhouse as described above and watered by sub-irrigation to prevent wash-off of the test compounds. After 20-22 days, the condition of the test plants as compared with that of the control plants was determined visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury and 100 corresponds to complété kill.
Colby’s équation was used to détermine the herbicidal effects expected from the mixtures (Colby, S.R. 1967. Calculation of the synergistic and antagonistic response of herbicide combinations. Weeds 15:20-22.).
The following équation was used to calculate the expected activity of mixtures containing two active ingrédients, A and B:
Expected = A + B - (A x B/100)
A = observed efficacy of active ingrédient A at the same concentration as used in the mixture.
B = observed efficacy of active ingrédient B at the same concentration as used in the mixture.
The compounds tested, application rates employed, plant species tested, and results are given in Tables 21-24.
Table 21. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Metribuzin Herbicidal Compositions on Weed Control in a Cereals Cropping System.
Compound A Benzyl Ester Metribuzin Visual Weed Control (%) - 21 DAA
SASKR KCHSC LAMPU
g ai/ha gai/ha Obs Exp Obs Exp Obs Exp
2.5 0 15 20 80
5 0 50 41 86
10 0 67 62 94
0 25 8 0 3
0 50 8 8 15
0 100 67 88 23
2.5 25 25 21 45 20 90 81
2.5 50 20 21 35 26 89 83
5 25 38 54 58 41 91 86
5 50 63 54 43 45 98 88
5 100 100 83 100 93 99 89
10 100 97 89 100 96 100 95
Compound A Benzyl Ester Metribuzin Visual Weed Control (%) - 21 DAA
CHEAL SINAR
gai/ha gai/ha Obs Exp Obs Exp
2.5 0 50 - 70 -
5 0 58 - 73 -
0 25 0 - 8 -
0 50 55 - 15 -
2.5 25 68 50 90 72
2.5 50 70 78 95 75
5 25 78 58 93 75
5 50 83 81 95 77
Table 22. Synergistic Activity ofFoliar-Applied Compound A Benzyl Ester and Isoproturon Herbicidal Compositions on Weed Control in a Cereals Cropping System.
Compound A Benzyl Ester Isoproturon Visual Weed Control (%) - 21 DAA
AMARE SINAR
gai/ha g ai/ha Obs Exp Obs Exp
2.5 0 20 - 70 -
5 0 38 - 73 -
0 375 3 - 13 -
0 750 10 - 40 -
2.5 375 43 22 84 74
2.5 750 60 28 88 82
5 375 55 39 89 76
5 750 70 44 84 84
Compound A Benzyl Ester Isoproturon Visual Weed Control (%) - 21 DAA
GALAP VERPE
gai/ha gai/ha Obs Exp Obs Exp
5 0 66 17
10 0 77 23
0 375 5 8
0 750 5 10
0 1500 27 13
5 375 68 68 18 23
5 750 80 68 28 25
5 1500 99 75 60 28
10 1500 97 83 70 34
Compound A Benzyl Ester Isoproturon Visual Weed Control (%) - 21 DAA
LAMPU
gai/ha g ai/ha Obs Exp
2.5 0 80
5 0 86
10 0 94
0 375 3
0 750 3
0 1500 13 -
2.5 375 83 81
2.5 750 89 81
5 375 89 86
5 750 91 86
5 1500 97 88
10 1500 97 95
Table 23. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Bentazon5 sodium Herbicidal Compositions on Weed Control in a Cereals Cropping System.
Compound A Benzyl Ester BentazonSodium Visual Weed Control (%) - 21 DAA
L·
IPC •HE
g ai/ha gai/ha Obs Exp
17.5 0 33 -
0 60 7 -
0 120 10 -
17.5 60 67 38
17.5 120 67 40
Compound A Benzyl Ester BentazonSodium Visual Weed Control (%) - 21 DAA
SE1 [TA BRSNW
gai/ha gai/ha Obs Exp Obs Exp
8.75 0 13 - 0 -
0 120 0 - 0 -
8.75 120 63 13 28 0
Table 24. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Bromoxynil Herbicidal Compositions on Weed Control in a Cereals Cropping System.
Compound A Benzyl Ester Bromoxynil Visual Weed Control (%) - 21 DAA
AMARE IPOHE
g ai/ha gai/ha Obs Exp Obs Exp
8.75 0 57 - 33 -
17.5 0 85 - 33 -
0 35 3 - 50 -
0 70 17 - 35 -
8.75 35 75 58 42 67
8.75 70 88 64 63 57
17.5 35 98 86 60 67
17.5 70 99 88 75 57
Compound A Benzyl Ester Bromoxynil Visual Weed Control (%) - 21 DAA
SETFA
gai/ha gai/ha Obs Exp
8.75 0 13 -
0 70 0 -
8.75 70 63 13
AMARE Amaranthus retrqflexus L. pigweed, redioot
BRSNW Brassica napus L. râpe, oilseed (winter)
CHEAL Chenopodium album L. lambsquarters, common
GALAP Galium aparine L. bedstraw, catchweed
IPOHE Ipomoea hederacea Jacq. momingglory, ivyleaf
KCHSC Kochia scoparia (L.) Schrad. kochia
LAMPU Lamium purpureum L. deadnettle, purple
SASKR Salsola tragus L. thistle, Russian
SETFA Setaria faberi Herrm. foxtail, giant
SINAR Sinapis arvensis L. mustard, wild
VERPE Veronica persica Poir. Speedwell, Persian
g ae/ha = grams acid équivalent per hectare g ai/ha = grams active ingrédient per hectare Obs = observed value
Exp = expected value as calculated by Colby’s équation DAA = days after application
Example IV. Evaluation of 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-2fluoro-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 équivalent basis.
Forms of compound A (compound of formula I) tested include:
Compound A Benzyl Ester
Other herbicidal components were appiied on an acid équivalent or active ingrédient basis and included the PSII-inhibiting herbicides, atrazine formulated as Atrazine® 90WDG, metribuzin formulated as Metribuzin 75DF, simazine formulated as Princep Caliber 90, tebuthiuron formulated as Spike 80DF, cyanazine (technical grade material), hexazinone (technical grade material), linuron (technical grade material), terbuthylazine (technical grade material), and diuron formulated as Diuron 4L.
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 concentrate (COC) 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) 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 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) 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.
-89For treatments comprised of formulated and technical compounds, weighed amounts of the technical materials can be piaced individually in 25 mL glass vials and dissolved in a volume of 97:3 (v/v) acetone/DMSO to obtain 12X stock solutions, and measured amounts of the formulated compounds can be piaced individually in 25 mL glass vials and diluted in a volume of 1.5% (v/v) COC or water to obtain 12X stock solutions. If a test compound does not dissolve readily, the mixture can be warmed and/or sonicated. Application solutions can be prepared by adding an appropriate amount of each stock solution (e.g., 1 mL) and diluted to the appropriate final concentrations with the addition of an appropriate amount of an aqueous mixture of 1.5% (v/v) COC so that the final spray solutions contain 1.25% (v/v) COC. As required, additional water and/or 97:3 (v/v) acetone/DMSO canbe 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 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 piaced 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. Supplémentai lighting was provided with overhead métal halide 1000-Watt lamps as necessary. After approximately 4 weeks, the condition ofthe test plants as compared with that of the untreated plants was determined visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury or growth inhibition and 100 corresponds to complété kill.
Colby’s équation was used to détermine the herbicidal effects expected from the mixtures (Colby, S.R. 1967. Calculation of the synergistic and antagonistic response of herbicide combinations. Weeds 15:20-22.).
The following équation was used to calculate the expected activity of mixtures containing two active ingrédients, A and B:
Expected = A + B - (A x B/l 00)
-90A = observed efficacy of active ingrédient A at the same concentration as used in the mixture.
B = observed efficacy of active ingrédient B at the same concentration as used in the mixture.
Some of the compounds tested, application rates employed, plant species tested, and results are given in Tables 25-32.
Table 25. Synergistic Activity of Soil-applied, Pre-emergence Applications of Compound A Benzyl Ester and Atrazine Herbicidal Compositions on Weed Control
Compound A Benzyl Ester Atrazine Visual Weed Control (%) - 32 DAA
XANST
g ae/ha g ai/ha Obs Exp
8 0 33
16 0 35
32 0 65
0 560 68
0 1120 40
8 560 95 78
16 560 100 79
• 32 ’ 560 - 75 • 89
8 1120 100 60
16 1120 100 61
32 1120 100 79
-91 Table 26. Synergistic Activity of Soil-applied, Pre-emergence Applications of Compound A
Benzyl Ester and Metribuzin Herbicidal Compositions on Weed Control
Compound A Benzyl Ester Metribuzin Visual Weed Control (%) - 27 DAA
SETFA
g ae/ha gai/ha Obs Exp
16 0 8 -
32 0 15 -
0 210 43 -
0 420 83 -
16 210 100 48
32 210 100 52
16 420 95 85
32 420 100 86
Table 27. Synergistic Activity of Soil-applied, Pre-emergence Applications of Compound A Benzyl Ester and Simazine Herbicidal Compositions on Weed Control
Compound A Benzyl Ester Simazine Visual Weed Control (%) - 33 DAA
XANST
gae/ha gai/ha Obs Exp
16 0 38 -
32 0 35 -
0 1120 70 -
0 2240 92 -
16 1120 77 82
32 1120 95 81
16 2240 100 95
32 2240 100 95
Table 28. Synergistic Activity of Soil-applied, Pre-emergence Applications of Compound A
Benzyl Ester and Tebuthiuron Herbicidal Compositions on Weed Control
Compound A Benzyl Ester Tebuthiuron Visual Weed Control (%) - 33 DAA
IPOHE
gae/ha gai/ha Obs Exp
16 0 0 -
32 0 5 -
0 420 87 -
0 840 90 -
16 420 93 87
32 420 93 87
16 840 100 90
32 840 100 91
Compound A Benzyl Ester Tebuthiuron Visual Weed Control (%) - 29 DAA
XANST
gae/ha gai/ha Obs Exp
16 0 0 -
32 0 5 -
0 210 40 -
0 3360 95 -
16 210 63 40
32 210 55 43
16 3360 100 95
32 3360 100 95
Table 29. Synergistic Activity of Soil-applied, Pre-emergence Applications of Compound A Benzyl Ester and Cyanazine Herbicidal Compositions on Weed Control
Compound A Benzyl Ester Cyanazine Visual Weed Control (%) - 27 DAA
BRAPP
gae/ha gai/ha Obs Exp
32 0 0 -
0 170 0 -
0 440 15 -
0 880 10 -
32 170 10 0
32 440 28 15
32 880 40 10
Table 30. Synergistic Activity of Soil-applied, Pre-emergence Applications of Compound A Benzyl Ester and Linuron Herbicidal Compositions on Weed Control
Compound A Benzyl Ester Linuron Visual Weed Control (%) - 27 DAA
BRAPP
gae/ha g ai/ha Obs Exp
16 0 0 -
32 0 0 -
0 620 0 -
16 620 15 0
32 620 20 0
Table 31. Synergistic Activity of Soil-applied, Pre-emergence Applications of Compound A Benzyl Ester and Tebuthylazine Herbicidal Compositions on Weed Control
Compound A Benzyl Ester Terbuthylazine Visual Weed Control (%) - 27 DAA
XANST
g ae/ha g ai/ha Obs Exp
16 0 10 -
32 0 25 -
0 1000 45 -
16 1000 83 51
32 1000 75 59
Table 32. Synergistic Activity of Soil-applied, Pre-emergence Applications of Compound A Benzyl Ester and Diuron Herbicidal Compositions on Weed Control
Compound A Benzyl Ester Diuron Visual Weed Control (%) - 29 DAA
ABUTH
g ae/ha g ai/ha Obs Exp
16 0 65
32 0 93
0 280 30
0 560 70
0 1120 90
16 280 90 76
32 280 100 95
16 560 100 90
32 560 100 98
16 1120 100 97
32 1120 100 99
Compound A Benzyl Ester Diuron Visual Weed Control (%) - 28 DAA
BRAPP ECHCG
g ae/ha gai/ha Obs Exp Obs Exp
16 0 0 - 0 -
32 0 5 - 0 -
0 280 0 - 25 -
0 560 35 - 65 -
16 280 45 0 35 25
32 280 25 5 23 25
16 560 100 35 80 65
32 560 100 38 98 65
Compound A Benzyl Ester Diuron Visual Weed Control (%) - 29 DAA
ECHCO SETFA SETVI
g ae/ha gai/ha Obs Exp Obs Exp Obs Exp
16 0 0 - 0 - 10 -
32 0 5 - 0 - 10 -
0 280 15 - 5 - 0 -
16 280 60 15 13 5 48 10
32 280 80 19 30 5 25 10
ABUTH BRAPP Abutilon theophrasti Medik. Brachiaria platyphylla (Groseb.) Nash or velvetleaf
5 Urochloa platyphylla (Nash) R.D. Webster signalgrass, broadleaf
ECHCG Echinochloa crus-galli (L.) P. Beauv. bamyardgrass
ECHCO Echinochloa colonum (L.) Link junglerice
IPOHE Ipomoea hederacea (L.) Jacq. momingglory, ivyleaf
SETFA Setaria faberi Herrm. foxtail, giant
10 SETVI Setaria viridis (L.) Beauv. foxtail, green
XANST Xanthium strumarium L. cocklebur, common
g ae/ha = grams acid équivalent per hectare
g ai/ha = grams active ingrédient per hectare
Obs = observed value
Exp = expected value as calculated by Colby’s équation
DAA = days after application
-95Example V. Evaluation of Postemergence Foliar-Applied Herbicidal Mixtures for General Weed Control
Seeds or root cuttings 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 126.6 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 9-30 days in a greenhouse with an approximate 14 hour photoperiod which was maintained at approximately 28° C during the day and 24° C during the night. Nutrients and water were added on a regular basis and supplémentai lighting was provided with overhead métal halide 1000-Watt lamps as necessary. The plants were employed for testing when they reached the BBCH11 to BBCH14 leaf stage.
Treatments consisted of the benzyl ester of 4-amino-3-chloro-5-fluoro-6-(4-chloro-2fluoro-3-methoxy-phenyl)pyridine-2-carboxylic acid (Compound A), formulated as a SC and a tebuthiuron containing herbicide (Spike® 80DF). A measured aliquot of Compound A was placed in 25 milliliter (mL) glass vial and diluted in a volume of distilled water or 1.25% volume/volume (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 glyphosate-containing herbicide and experimental compound mixtures were prepared by adding the stock solutions to the appropriate amount of dilution solution to form 12 mL spray solution with active ingrédients in two-way combinations. Formulated compounds were applied to the plant material with an overhead Mandel track sprayer equipped with 8002E nozzles calibrated to deliver 187 L/ha over an application area of 0.503 square meters (m2) at a spray height of 18 inches (43 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 approximately 14 days, the condition of the test plants, as compared with that of the control plants, was determined visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury and 100 corresponds to complété kill.
Colby’s équation was used to détermine the herbicidal effects expected from the mixtures (Colby, S.R. 1967. Calculation ofthe synergistic and antagonistic response ofherbicide combinations. Weeds 15:20-22.).
-96The following équation was used to calculate the expected activity of mixtures containing two active ingrédients, A and B:
Expected = A + B - (A x B/100)
A = observed efficacy of active ingrédient A at the same concentration as used in the mixture.
B = observed efficacy of active ingrédient B at the same concentration as used in the mixture.
Some of the compounds tested, application rates employed, plant species tested, and results are given in Table 33.
Table 33. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Spike 80DF (Tebuthiuron) Herbicidal Compositions formulated in 1.25% (v/v) crop oil concentrate in water on General Weed Controi.
Application Rate (g/ha) ECHCG CIRAR BRSNN CYPES
Compound A Benzyl Ester Spike Obs Exp Obs Exp Obs Exp Obs Exp
4 0 30 - 35 10 - 0 -
8 0 50 - 40 15 - 65 -
16 0 60 - 50 30 - 85 -
0 140 0 - 25 10 - 0 -
0 280 0 - 30 20 - 0 -
0 560 0 - 55 15 - 0 -
4 140 75 30 55 51 30 19 85 0
8 140 85 50 75 54 65 23 80 65
16 140 95 60 95 71 70 37 90 85
4 280 80 30 85 55 65 28 80 0
8 280 80 50 90 58 80 32 85 65
16 280 90 60 95 73 95 44 95 85
4 560 85 30 90 62 80 23 60 0
8 560 80 50 95 65 90 44 75 65
16 560 90 60 100 77 100 41 100 85
ECHCG
CIRAR BRSNN CYPES
Echinochloa crus-galli L. Cirsium arvense (L.) Scop.
Brassica napus L. Cyperus esculentus L.
bamyardgrass thistle, Canada râpe, oilseed nutsedge, yellow

Claims (11)

  1. WHAT IS CLAIMED IS:
    1. A synergistic herbicidal composition comprising a herbicidally effective amount of (a) a compound of the formula (I)
    NH,
    OH or an agriculturally acceptable sait or ester thereof and (b) at least one compound, or an agriculturally acceptable sait, carboxylic acid, carboxylate sait, or ester thereof, selected from the group consisting ofatrazine, bentazon, bentazon-sodium, bromoxynil, chlorotoluron, cyanazine, diuron, hexazinone, ioxynil, isoproturon, linuron, methibenzuron, metribuzin, propanil, pyridate, siduron, simazine, simetryne, tebuthiuron, and terbuthylazine.
  2. 2. The composition of claim 1, wherein (a) is the compound of formula (I), a Cm alkyl ester of the compound of formula (I), or a benzyl ester of the compound of formula (I).
  3. 3. The composition of any of claims 1 -2, further comprising an agriculturally acceptable adjuvant or carrier.
  4. 4. The composition of any of claims 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)
    NH,
    Cl
    OH or an agriculturally acceptable sait or ester thereof and (b) is at least one compound, or an agriculturally acceptable sait, carboxylic acid, carboxylate sait, or ester thereof, selected from the group consisting of: atrazine, bentazon, bentazon-sodium, bromoxynil, chlorotoluron, cyanazine, diuron, hexazinone, ioxynil, isoproturon, linuron, methibenzuron, metribuzin, propanil, pyridate, siduron, simazine, simetryne, tebuthiuron, and terbuthylazine.
  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 claims 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, canola, sugar beet, soybean, cotton, pineapple, pastures, grasslands, rangelands, fallowland, turf, tree and vine orchards, aquatics, industrial végétation management (IVM) or rights of way (ROW).
  8. 8. The method of any of claims 5-7, wherein the (a) and (b) are appiied pre-emergently to the weed or the crop.
  9. 9. The method of any of claims 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 I inhibitor-, photosystem II 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 any of claims 5-10, wherein the undesirable végétation comprises a herbicide résistant or tolérant weed.
OA1201500032 2012-07-24 2013-07-19 Herbicidal compositions comprising 4-amino3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxylphenyl) pyridine-2-carboxylic acid or a derivative thereof and certain PS II inhibitors. OA17280A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US61/675,089 2012-07-24
US13/840,488 2013-03-15

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Publication Number Publication Date
OA17280A true OA17280A (en) 2016-04-29

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