HERBICIDE COMPOSITIONS UNDERSTANDING 4-AMINO-3-CHLOR-5-FLUORO-6- (4-CHLOR-2-FLUORO-3-METOXYPHENYL) P

专利摘要:
"Herbicide compositions comprising 4-amino-3-chloro-5-fluoro-6- (4-chloro-2-fluoro-3-methoxyphenyl) pyridine-2-carboxylic acid or a derivative thereof. mo and certain ps ii inhibitors ". In this application synergistic herbicide compositions containing (a) a compound of formula (I) are provided. or an agriculturally acceptable salt or ester thereof and (b) a ps ii inhibitor, including but not limited to atrazine, bentazon sodium, bromoxinil, chlorotoluron, cyanazine, diuron, hexazinone, ioxinyl, isoproturon, linuron, methyl 10 benzuron, metribuzin, propanyl, pyridate, siduron, simazine, symmetrine, tebutyron and terbuthylazine, or a salt or ester thereof. The compositions and methods provided in this application provide undesirable vegetation control, for example in directly sown, water-sown and transplanted rice, cereals, wheat, barley, oats, rye, sorghum, maize or maize, 15 cane. -sugar, sunflower, rapeseed, canola, beet, soybean, cotton, pineapple, grassland, grassland, natural grassland, fallow, lawn, vine orchard, aquatic, large crops, vegetables, industrial vegetation management (ivm) or tracks of servitude (row).
公开号:BR102013018536A2
申请号:R102013018536-1
申请日:2013-07-19
公开日:2018-05-15
发明作者:Yerkes Carla；Mann Richard；Schmitzer Paul；Satchivi Norbert
申请人:Dow Agrosciences Llc；
IPC主号:

专利说明:

Invention Patent Descriptive Report for "COMPOSITIONS OF HERBICIDE COMPRISING ACID 4-AMINO-3-CHLORINE-5-FLUOR-6- (4-CHLORINE-2-FLUOR-3-METOXYphenyl) PYRIDINE-2-CARBOXYLI-CO OR A DERIVED OF THE SAME AND CERTAIN INHIBITORS OF PS II ".
Priority claim This patent application claims the benefit of United States Provisional Patent Application No. 61 / 675,089 filed on July 24, 2012, and United States Patent Application No. Serial 13 / 840,488, filed on March 15, 2013, the disclosure of each of which is incorporated in this order by reference in its entirety. Field Herbicide compositions comprising and methods for controlling undesirable vegetation using (a) 4-amino-3-chloro-5-fluoro-6- (4-chloro-2-fluoro-3-methoxyphenyl) acid are provided in this application ) pyridine-2-carboxylic or an agriculturally acceptable ester or salt thereof and (b) a photosystem (PS) II inhibitor selected from the group consisting of: atrazine, bentazon-sodium, bromoxynil, chlorotoluron, cyanazine, diuron, hexazi -nona, ioxinil, isoproturon, linuron, metibenzuron, metribuzin, propanil, pyrida-to, siduron, simazine, symmetry, tebutiuron and terbuthylazine, or derivative, for example, salt or ester thereof.
Background The protection of crops from weeds and other vegetation that inhibit crop growth is a problem that constantly occurs in agriculture. To help combat this problem, researchers in the field of synthetic chemistry have produced an extensive variety of chemicals and chemical formulations effective in controlling such unwanted growth. Chemical herbicides of many types have been described in the literature and a large number are in commercial use. However, there remains a need for compositions and methods that are effective in controlling undesirable vegetation.
Summary Several modalities are mentioned below.  In the embodiments, the ratio of compound (a) to compound (b) can be expressed in units of weight by weight (g to g), gae / ha to gae / ha or gae / ha to gai / ha.  1.  A synergistic herbicidal composition comprising a herbicidally effective amount of (a) a compound of formula (I) or an agriculturally acceptable salt or ester thereof and (b) atrazine, bentazon, bentazon-sodium, bromoxynil, chlorotoluron, cyanazine, diuron, hexazinone, ioxynil, isoproturon, linuron, metibenzuron, metribuzin, propanil, pyridate, siduron, simazine, symmetry, tebutiuron or terbuthylazine or agriculturally acceptable salt or ester thereof.  2.  The composition of modality 1, wherein (a) is a C1-4 alkyl or benzyl ester of compound (I).  3.  The composition of modality 1, wherein (a) is a C1-4 alkyl ester of compound (I).  4.  The composition of modality 2, wherein (a) is a benzyl ester of compound (I).  5.  The composition of modality 1, wherein (a) is the compound of formula (I), which is carboxylic acid.  6.  The composition of modality 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is atrazine.  7.  The composition of modality 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is bentazon or bentazon-sodium.  8.  The composition of modality 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is bromoxynil or bromoxynil octanoate.  9.  The composition of modality 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is chlorotoluron.  10.  The composition of modality 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is cyanazine.  11.  The composition of modality 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is diuron.  12.  The composition of modality 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is hexazino-na.  13.  The composition of modality 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is ioxynil.  14.  The composition of modality 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is isoproturon.  15.  The composition of modality 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is linuron.  16.  The composition of modality 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is metibenzuron.  17.  The composition of modality 1, where (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is metribuzin.  18.  The composition of modality 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is propanyl.  19.  The composition of modality 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is pyridate.  20.  The composition of modality 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is siduron.  21.  The composition of modality 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is simazine.  22.  The composition of modality 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is symmetry.  23.  The composition of modality 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is tebutiuron.  24.  The composition of mode 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is terbuthylazin.  25.  The composition of any one of embodiments 1 to 24, further comprising a herbicide phytoprotectant.  26.  The composition of modality 2, in which the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to atrazine or agriculturally acceptable salt thereof is selected from the group of proportions and proportions ranges consisting of: approximately 1: 2240 to approximately 6: 1, approximately 1: 1120 to approximately 3: 1, approximately 1: 256 to approximately 1:16, approximately 6: 1, approximately 1: 7, approximately 1: 9, approximately 1:16, approximately 1: 17.5, approximately 1:32, approximately 1:35, approximately 1:64, approximately 1:70, approximately 1: 128, approximately 1: 140, approximately 1: 256, and a-approximately 1: 2240, or within any defined range between any pair of preceding values.  27.  The composition of modality 2, in which the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to bentazon, bentazon-sodium or agriculturally acceptable salt thereof is selected from the group of ratios and ratios consisting of: approximately 1: 1120 to approximately 3: 1, to-approximately 1: 560 to approximately 2: 1, approximately 1: 256 to approximately 1.4: 1, approximately 1:96 to approximately 1: 3, 4, approximately 3: 1, approximately 1: 3. 4, approximately 1: 6, approximately 1: 7, approximately 1:12, approximately 1:14, approximately 1:16, approximately 1:20, approximately 1:24, approximately 1:26, approximately 1:32, approximately 1: 40, approximately 1:48, approximately 1: 52.5, approximately 1:96, approximately 1: 256, and approximately 1: 1120, or within any defined range between any pair of the preceding values.  28.  The composition of modality 2, in which the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to bromoxynil or agriculturally acceptable salt or ester thereof is selected from the group of ranges of proportions and proportions consisting in: from approximately 1: 280 to approximately 12: 1, approximately 1: 140 to approximately 6: 1, approximately 1:70 to approximately 3: 1, approximately 1:35 to approximately 2: 1, approximately 1: 17.5 to approximately 1: 1, approximately 12: 1, approximately 1: 1, approximately 1: 2, approximately 1: 4, approximately 1: 4.4, approximately 1: 8, approximately 1: 12.5, approximately 1: 17.5 , and approximately 1: 280, or within any defined range between any pair of the preceding values.  29.  The composition of embodiment 2, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to chlorotoluron or agriculturally acceptable salt or ester thereof is approximately 1: 1750 to approximately 1.5: 1 .  30.  The composition of modality 2, in which the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to cyanazine or agriculturally acceptable salt thereof is selected from the group of proportions and proportions ranges consisting of: approximately 1: 2650 to approximately 6: 1, approximately 1: 1325 to approximately 3: 1, approximately 1: 662 to approximately 2: 1, approximately 1: 110 to approximately 1: 5.3, approximately 6: 1, approximately 1: 5.3, approximately 1: 8.6, approximately 1: 13.8, approximately 1: 17.2, approximately 1:25, approximately 1:27 ,. 5, approximately 1: 34.4, approximately 1: 110, approximately 1: 662, approximately 1: 1325, and approximately 1: 2650, or within any defined range between any pair of the preceding values.  31.  The composition of modality 2, in which the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to diuron or agriculturally acceptable salt thereof is selected from the group of proportions and proportions ranges consisting of: a-approximately 1: 3600 to approximately 6: 1, approximately 1: 1800 to approximately 3: 1, approximately 1: 900 to approximately 1: 2, approximately 1:70 to approximately 1: 9, approximately 6: 1, a-approximately 1: 9, approximately 1: 17.5, approximately 1:35, to approximately 1:70, approximately 1: 900, approximately 1: 1800, and approximately 1: 3600, or within any defined range between any pair of values precedents.  32.  The composition of modality 2, in which the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to hexazinone or agriculturally acceptable salt thereof is selected from the group of proportions and proportions ranges consisting of: approximately 1: 2500 to approximately 12: 1, approximately 1: 1250 to approximately 2: 1, approximately 1: 625 to approximately 1: 1, approximately 1: 156 to approximately 1:20, approximately 12: 1, approximately 1:20, approximately 1:39, approximately 1:78, approximately 1: 156, and approximately 1: 2500, or within any defined range between any pair of the preceding values.  33.  The composition of modality 2, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to ioxynil or agriculturally acceptable salt or ester thereof is selected from the group of proportions and proportions ranges consisting of at: approximately 1: 200 to approximately 12: 1, approximately 1: 100 to approximately 1: 1, approximately 1: 37.5 to approximately 1: 9, approximately 12: 1, approximately 1: 9.4, approximately 1:19 , approximately 1: 37.5, and approximately 1: 200, or within any defined range between any pair of the preceding values.  34.  The composition of modality 2, in which the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to isoproturon or agriculturally acceptable salt thereof is selected from the group of proportions and proportions ranges consisting of: approximately 1: 750 to approximately 12: 1, approximately 1: 375 to approximately 6: 1, approximately 1: 600 to approximately 1: 37.5, approximately 1: 300 to approximately 1:75, approximately 1: 750, approximately 1: 600, approximately 1: 375, approximately 1: 300, approximately 1: 150, approximately 1:75, approximately 1: 37.5, approximately 1: 1, approximately 6: 1, and approximately 12: 1.  35.  The composition of modality 2, in which the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to linuron or agriculturally acceptable salt thereof is selected from the group of proportions and proportions ranges consisting of: from approximately 1: 2250 to approximately 6: 1, approximately 1: 1125 to approximately 3: 1, approximately 1: 562 to approximately 1: 1, approximately 1:39 to approximately 1:19, approximately 6: 1, a-approximately 3 : 1, approximately 1: 19.4, approximately 1: 38.8, approximately 1: 562, approximately 1: 1125, and approximately 1: 2250, or within any defined range between any pair of the preceding values.  36.  The composition of modality 2, in which the weight ratio of the compound of the formula (I) or agriculturally acceptable salt or ester thereof to metibenzuron or agriculturally acceptable salt thereof is selected from the group of proportions and proportions ranges consisting of: approximately 1: 1400 to approximately 4: 1, approximately 1: 700 to approximately 2: 1, and approximately 1: 350 to approximately 1: 1.  37.  Composition mode 2 in which the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to metribuzin or agriculturally acceptable salt thereof is selected from the group of proportions and proportions ranges consisting of: approximately 1: 2800 to approximately 6: 1, approximately 1: 1400 to approximately 3: 1, approximately 1: 700 to approximately 2: 1, approximately 1: 168 to approximately 1.3: 1, approximately 1:26 to approximately 1: 5 approximately 6: 1, approximately 3: 1, approximately 2: 1, approximately 1: 3, approximately 1: 5, approximately 1: 6.7, approximately 1:10, approximately 1:13, approximately 1:20, approximately 1 : 26, approximately 1: 168, approximately 1: 700, approximately 1: 1400, and approximately 1: 2800, or within any defined range between any pair of the preceding values.  38.  The composition of modality 2 in which the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to propanyl or agriculturally acceptable salt thereof is selected from the group of proportions and proportions ranges consisting of: approximately 1: 2800 to approximately 1: 1, approximately 1: 1400 to approximately 1: 4, approximately 1: 767 to approximately 1:24, approximately 1: 767 to approximately 1:12, approximately 1: 384 to approximately 1:48, approximately 1: 1, approximately 1: 4, approximately 1:12, approximately 1:24, approximately 1:48, approximately 1:96, approximately 1: 173, approximately 1: 192, approximately 1: 210, approximately 1 : 384, approximately 1: 560, approximately 1: 767, approximately 1: 1400, and approximately 1: 2800, or within any defined range between any pair of previous values.  39.  The composition of modality 2, in which the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to pyridate or agriculturally acceptable salt thereof is selected from the group of proportions and proportions ranges consisting of: a-approximately 1: 800 to approximately 12: 1, approximately 1: 800 to approximately 6: 1, approximately 1: 800 to approximately 3: 1, a-approximately 1: 800 to approximately 1: 1, approximately 1: 400 to approximately 6: 1, approximately 1: 400 to approximately 3: 1, to-approximately 1: 400 to approximately 1: 1, and approximately 1: 200 to approximately 1:16.  40.  The composition of modality 2, in which the weight ratio of the compound of the formula (I) or agriculturally acceptable salt or ester thereof to siduron or agriculturally acceptable salt thereof is selected from the group of proportions and proportions ranges consisting of: a-approximately 1: 4500 to approximately 2: 1, approximately 1: 2250 to approximately 1: 1, approximately 1: 1125 to approximately 1: 5: and approximately 1: 625 to approximately 1:50.  41.  The composition of modality 2, in which the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to simazine or agriculturally acceptable salt thereof is selected from the group of proportions and proportions ranges consisting of: approximately 1: 4250 to approximately 2: 1, approximately 1: 2125 to approximately 1: 1, approximately 1: 560 to approximately 1: 8, approximately 1: 280 to approximately 1: 17.5, approximately 1: 140 to approximately 1: 17.5, approximately 2: 1, approximately 1: 8, approximately 1: 17.5, approximately 1:35, approximately 1:70, approximately 1: 140, approximately 1: 280, approximately 1: 560, approximately 1: 2125 , and approximately 1: 4250, or within any defined range between any pair of preceding values.  42.  The composition of modality 2, in which the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to symmetry or agriculturally acceptable salt thereof is selected from the group of proportions and proportions ranges consisting of: approximately 1: 1000 to approximately 12: 1, approximately 1: 500 to approximately 6: 1, approximately 1: 250 to approximately 1: 1, approximately 1:56 to approximately 1: 3.5, approximately 12: 1, approximately 6: 1, approximately 1. 3.5, approximately 1: 1, approximately 1: 7, approximately 1:14, approximately 1:28, approximately 1:56, approximately 1: 250, approximately 1: 500, and approximately 1: 1000, or within any range defined between any pair of preceding values.  43.  The composition of modality 2, in which the weight ratio of the compound of the formula (I) or agriculturally acceptable salt or ester thereof to tebutiuron or agriculturally acceptable salt thereof is selected from the group of proportions and proportions ranges consisting of: approximately 1: 2240 to approximately 2: 1, approximately 1: 1120 to approximately 1: 1, approximately 1: 840 to approximately 1: 6, approximately 1: 210 to approximately 1: 6, approximately 2: 1, approximately - 1: 1, approximately 1: 2, approximately 1: 3, approximately 1: 6, approximately 1: 9, approximately 1:13, approximately 1: 17.5, approximately 1:26, approximately 1:35, approximately 1: 52.5 approximately 1:70, approximately 1: 105, approximately 1: 140, approximately 1: 210, approximately 1: 840, and approximately 1: 2240, or within any defined range between any pair of the preceding values.  44.  The composition of modality 2, in which the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to terbuthylazine or agriculturally acceptable thereof is selected from the group of proportions and proportions ranges consisting of: approximately 1: 1500 to approximately 2.4: 1, approximately 1: 750 to approximately 1: 1, approximately 1: 375 to approximately 1: 3, approximately 1: 200 to approximately 1:10, approximately 1: 62.5 to approximately 1 : 31, approximately 2.4: 1, approximately 1: 31.3, approximately 1: 62.5, and approximately 1: 1500, or within any defined range between any pair of the preceding values.  45.  The composition of any one of embodiments 1 to 44, further comprising an agriculturally acceptable adjuvant or vehicle.  46.  The composition of any of modalities 1 to 44 that is synergistic as determined by Colby's equation.  47.  A method of controlling undesirable vegetation that comprises contact with vegetation or its locus or application to soil or water to prevent the emergence or growth of vegetation in the composition of any of modalities 1 to 46.  48.  A method of controlling undesirable vegetation comprising contact with vegetation or the locus thereof or application to soil or water to prevent the appearance or growth of vegetation of a herbicidally effective amount of (a) a compound of formula (I) or an agriculturally acceptable salt or ester thereof and (b) atrazine, bentazon, bentazon-sodium, bromoxynil, chlorotoluron, cyanazine, diuron, hexazinone, ioxynil, isoproturon, linuron, metibenzuron, metribuzin, propanyl, pyridate, siduron, pyridate, siduron symmetry, tebutiuron or terbuthylazine or agriculturally acceptable salt or ester thereof.  49.  The 47 or 48 method, in which the method is practiced on at least one member of the group consisting of rice directly sown, sown in water and transplanted, cereals, wheat, barley, oatmeal, rye, sorghum, corn / maize , sugar cane, sunflower, rapeseed, canola, beet, soy, cotton, pineapple, pasture, pasture, natural pasture, fallow, lawn, tree and vine orchards, aquatic, industrial vegetation management (IVM) or strips of servitude (ROW).  50.  The 47 or 48 method, in which the undesirable vegetation is immature.  51.  The 47 or 48 method, in which (a) and (b) are applied to water.  52.  The 51 method, in which the water is part of a flooded rice field.  53.  The method of modality 47 or 48, in which (a) and (b) are applied pre-emergence to weed or crop.  54.  The 47 or 48 modality method, in which (a) and (b) are applied post-emergence to weed or crop.  55.  The 47 or 48 modality method, in which undesirable vegetation is controlled in glyphosate-tolerant cultures, 5-enolpyruvylshikimato-3-phosphate synthase (EPSP) inhibitor, glufosinate, glutamine-synthetase inhibitor, dicamba, auxin phenoxy, pyridyloxy auxin, synthetic auxin, auxin transport inhibitor, aryloxyphenoxypropionate, cyclohexanedione, phenylpyrazoline, acetyl CoA carboxylase inhibitor (ACCase), imidazolinone, sulfonylurea, pyrimidinylthiobenzoate, triazolopyrimidine, acetonyl acid, sulfonyl acetate, sulfonyl acid) synthase (AHAS), 4-hydroxyphenyl-pyruvate dioxigenase (HPPD) inhibitor, phytoene desaturase inhibitor, carotenoid biosynthesis inhibitor, protoporphyrinogen oxidase (PPO) inhibitor, cellulose biosynthesis inhibitor, mitosis inhibitor, microtubule inhibitor, microtubule inhibitor very long chain fatty acid inhibitor, fatty acid and lipid biosynthesis inhibitor, fo-t inhibitor ossystem I, photosystem II inhibitor, triazine or bromoxynil.  56.  The method of modality 55, in which the tolerant crop has multiple or stacked traits conferring resistance or tolerance to multiple herbicides or multiple modes of action.  57.  The 47 or 48 method, wherein the undesirable vegetation comprises a herbicide resistant or tolerant weed.  58.  The method of modality 57, in which the resistant or tolerant weed is a biotype with resistance or tolerance to multiple herbicides, multiple chemical classes, multiple modes of herbicide action or through multiple resistance mechanisms.  59.  The method of modality 57, in which the resistant or tolerant weed is a biotype resistant or tolerant to acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors, photosystem II inhibitors, acetyl CoA carboxylase inhibitors (ACCase), synthetic auxins, auxin transport inhibitors, photosystem I inhibitors, 5-enolpyruvylshikimato-3-phosphate synthase (EPSP) inhibitors, microtubule assembly inhibitors, fatty acid and lipid synthesis inhibitors, protoporphyrinogen oxidase (PPO) inhibitors , carotenoid biosynthesis inhibitors, very long chain fatty acid inhibitors (VLCFA), phytene desaturase (PDS) inhibitors, glutamine synthetase inhibitors, 4-hydroxyphenyl-pyruvate dioxigenase (HPPD) inhibitors, mitosis inhibitors, biosynthesis inhibitors cellulose, herbicides with multiple modes of action, quinclo-rac, arylaminopropionic acids, difenzoquat, endothall or organoarsenic.  60.  Methods of controlling undesirable vegetation including the step of applying a herbicidally effective amount of at least one mixture according to the twenty-sixth modality in which the amount of the mixture is applied in a rate, expressed in gai / ha or ga-e / ha of atrazine selected from the group of rates and rate ranges consisting of approximately: 50, 140, 280, 560, 1120, 2240, and 4400 or within any range defined between any pair of the preceding values.  61.  The methods according to the twenty-sixth or twenty-seventh modalities in which the controlled plant is at least one plant selected from the group consisting of: BRAPP, CYPIR, ECHCG, ECHCO and XANST, yet other modalities include control of plants of the genera consisting in: Brachiaria or Urochloa, Echinochloa, Bulbos-choenus and Xanthium.  62.  Methods for controlling undesirable vegetation comprising the step of applying a herbicidally effective amount of at least one mixture according to the twenty-seventh modality in which the amount of the mixture is applied in a rate, expressed in gai / ha or gae / ha of bentazon or bentazon-sodium selected from the group of rates and rate ranges consisting of approximately: 60, 105, 120, 210, 420, 840, 1120, and 2240, or within any range defined between any pair of the preceding values.  63.  The methods according to the twenty-seventh or sixty-second modalities in which the controlled plant is at least one plant selected from the group consisting of: BRSNW, COMBE, E-CHCG, ECHOR, IPOHE, LEFCH, SCPMA and SETFA, yet others modalities include control of plants of the genera consisting of: Brassica, Commelina, Echinochloa, Ipomoea, Leptochloa, Bolboschoenus or Schoe-noplectus and Xanthium.  64.  Methods of controlling undesirable vegetation comprising the step of applying a herbicidally effective amount of at least one mixture according to the twenty-eighth modality in which the amount of the mixture is applied in a rate, expressed in gai / ha or gae / ha of bromoxynil selected from the group of rates and rate ranges consisting of approximately: 25, 35, 70, 140, 280, or 560 within any defined range between any pair of the preceding values.  65.  The methods according to the twenty-eighth or sixty-fourth modalities in which the controlled plant is at least one plant selected from the group consisting of: AMARE, ECHCG, IPOHE and SETFA, yet other modalities include control of plants of the genera consisting of: Amaranthus, Echinochloa, Ipomoea and Setaria.  66.  Methods of controlling undesirable vegetation comprising the step of applying a herbicidally effective amount of at least one mixture according to the twenty-ninth modality in which the amount of the mixture is applied in a rate, expressed in gai / ha or gae / ha of chlorotoluron selected from the group of rates and rate ranges consisting of approximately: 200, 400, 800, 1600, or 3500 within any defined range between any pair of the preceding values.  67.  Methods for controlling undesirable vegetation comprising the step of applying a herbicidally effective amount of at least one mixture according to the thirtieth modality in which the amount of the mixture is applied in a rate, expressed in gai / ha or gae / ha of cyanazine selected from the group of rates and rate ranges consisting of approximately: 50, 170, 275, 440, 880, 1325, 2650, or 5300 within any range defined between any pair of the preceding values.  68.  The methods according to the thirty or sixty-seventh modalities in which the controlled plant is at least one plant selected from the group consisting of: BRAPP and IPOHE, yet other modalities include control of plants of the genera consisting of: Bra-chiaria or Urochloa and Ipomoea.  69.  Methods for controlling undesirable vegetation comprising the step of applying a herbicidally effective amount of at least one mixture according to the thirty-first modality in which the amount of the mixture is applied at a rate, expressed in gai / ha or gae / ha of diuron selected from the group of rates and rate ranges consisting of approximately: 50, 100, 140, 280, 560, 1120, 2240, 4480, or 7200 within any range defined between any pair of the preceding values.  70.  Methods according to the thirty-first or sixty-ninth modalities in which the controlled plant is at least one plant selected from the group consisting of: ABUTH, BRAPP, ECHCG, E-CHCO, SETFA and SETVI, yet other modalities include plant control of the genres consisting of: Abutilon, Brachiaria or Urochloa, Echinoc-hloa and Seta ria.  71.  Methods of controlling undesirable vegetation comprising the step of applying a herbicidally effective amount of at least one mixture according to the thirty-second modality in which the amount of the mixture is applied in a rate, expressed in gai / ha or gae / ha of hexazinone selected from the group of rates and rate ranges consisting of approximately: 25, 50, 100, 200, 400, 625, 1250, 2500, or 5000 within any range defined between any pair of the preceding values.  72.  Methods according to the thirty-second or seventy-first modalities in which the controlled plant is at least one plant selected from the group consisting of: ECHCG, ECHCO and I-POHE, yet other modalities include control of plants of the genera consisting of: Echinochloa and Ipomoea.  73.  Methods of controlling undesirable vegetation comprising the step of applying a herbicidally effective amount of at least one mixture according to the thirty-third modality in which the amount of the mixture is applied in a rate, expressed in gai / ha or gae / ha of ioxinil selected from the group of rates and rate ranges consisting of approximately: 25, 50, 100, 200, 300, or 400 within any range defined between any pair of the preceding values.  74.  Methods according to the thirty-third or seventy-third modalities in which the controlled plant is at least one plant selected from the group consisting of: IPOHE, yet other modalities include control of plants of the genera consisting of: Ipo-moea.  75.  Methods of controlling undesirable vegetation comprising the step of applying a herbicidically effective amount of at least one mixture according to the thirty-fourth modality in which the amount of the mixture is applied in a rate, expressed in gai / ha or gae / ha of isoproturon selected from the group of rates and rate ranges consisting of approximately: 25, 50, 100, 200, 400, 800, or 1500 within any defined range between any pair of the preceding values.  76.  Methods for controlling undesirable vegetation comprising the step of applying a herbicidally effective amount of at least one mixture according to the thirty-fifth modality in which the amount of the mixture is applied in a rate, expressed in gai / ha or gae / ha of linuron selected from the group of rates and rate ranges consisting of approximately: 50, 100, 200, 400, 620, 1125, 2250, or 4500 within any range defined between any pair of the preceding values.  77.  Methods according to the thirty-fifth or seventy-sixth modalities in which the controlled plant is at least one plant selected from the group consisting of: BRAPP, yet other modalities include control of plants of the genera consisting of: Brachiaria or Urochloa.  78.  Methods of controlling undesirable vegetation comprising the step of applying a herbicidically effective amount of at least one mixture according to the thirty-sixth modality in which the amount of the mixture is applied in a rate, expressed in gai / ha or gae / ha of metibenzuron selected from the group of rates and rate ranges consisting of approximately: 35, 70, 140, 280, 560, 700, 1400, or 2800 within any range defined between any pair of the preceding values.  79.  Methods of controlling undesirable vegetation comprising the step of applying a herbicidically effective amount of at least one mixture according to the thirty-seventh modality in which the amount of the mixture is applied in a rate, expressed in gai / ha or gae / ha of metribuzin selected from the group of rates and rate ranges consisting of approximately: 25, 50, 100, 210, 420, 840, 1680, 3360, or 5600 within any range defined between any pair of the preceding values.  80.  Methods according to the thirty-seventh or seventy-ninth modalities in which the controlled plant is at least one plant selected from the group consisting of: CHEAL, KCHSC, LAMPU, SAS-KR, SETFA, SINAR, yet other modalities include plant control of the genera consisting of: Chenopodium, Kochia, Lamium, Salsola, Seta-ria and Sinapsis.  81.  Methods of controlling undesirable vegetation comprising the step of applying a herbicidally effective amount of at least one mixture according to the thirty-eighth modality in which the amount of the mixture is applied in a rate, expressed in gai / ha or gae / ha of propanil selected from the group of rates and rate ranges consisting of approximately: 60, 120, 420, 840, 1680, 3360, or 5600 within any range defined between any pair of the preceding values.  82.  Methods according to the thirty-eighth or eighty-first modalities that the controlled plant is at least one plant selected from the group consisting of: COMBE, ECHCG, ECHCO, I-POHE and SCPMA, yet other modalities include control of plants of the genera consisting in: Commelina, Echinochloa, Ipomoea, and Bolboschoe-nus or Schoenoplectus.  83.  Methods of controlling undesirable vegetation comprising the step of applying a herbicidally effective amount of at least one mixture according to the thirty-ninth modality in which the amount of the mixture is applied in a rate, expressed in gai / ha or gae / ha of pyridate selected from the group of rates and rate ranges consisting of approximately: 25, 50, 100, 200, 400, 800, or 1600 within any range defined between any pair of the preceding values.  84.  Methods of controlling undesirable vegetation comprising the step of applying a herbicidically effective amount of at least one mixture according to the fortieth modality in which the amount of the mixture is applied in a rate, expressed in gai / ha or gae / ha of siduron selected from the group of rates and rate ranges consisting of approximately: 70, 140, 280, 560, 1120, 2240, 4480, or 9000 within any range defined between any pair of the preceding values.  85.  Methods of controlling undesirable vegetation comprising the step of applying a herbicidally effective amount of at least one mixture according to the forty-first modality in which the amount of the mixture is applied in a rate, expressed in gai / ha or gae / ha of simazine selected from the group of rates and rate ranges consisting of approximately: 70, 140, 280, 560, 1120, 2240, 4480, or 8500 within any range defined between any pair of the preceding values.  86.  Methods according to the forty-first or eighty-fifth modalities in which the controlled plant is at least one plant selected from the group consisting of: BRAPP, ECHCG, E-CHCO, CYPIR and XANST, yet other modalities include plant control of the genera consisting of: Brachiaria or Urochloa, Echinochloa, Cyperus and Xanthium.  87.  Methods of controlling undesirable vegetation comprising the step of applying a herbicidally effective amount of at least one mixture according to the forty-second modality in which the amount of the mixture is applied in a rate, expressed in gai / ha or gae / ha of symmetrine selected from the group of rates and rate ranges consisting of approximately: 25, 50, 112. 5, 225, 450, 900, 1350, and 2000 within any defined range between any pair of preceding values.  88.  Methods according to the forty-second or eight-seventh modalities in which the controlled plant is at least one plant selected from the group consisting of: CYPIR, CYPRO, ECH-CO, ECHOR, FIMMI and LEFCH, yet other modalities include control of plants of the genera consisting of: Cyperus, Echinochloa, Fimbristylis and Leptochloa.  89.  Methods of controlling undesirable vegetation comprising the step of applying a herbicidally effective amount of at least one mixture according to the forty-third modality in which the amount of the mixture is applied in a rate, expressed in gai / ha or gae / ha of tebutiuron selected from the group of rates and rate ranges consisting of approximately: 70, 140, 210, 280, 420, 560, 840, 1680, 3360, and 4480 within any range defined between any pair of the preceding values.  90.  Methods according to the forty-third or eight-ninth modalities in which the controlled plant is at least one plant selected from the group consisting of: BRSNN, CIRAR, CYPES, IPOHE and XANST, yet other modalities include control of plants of the genera consisting of: Brassica, Cirsium, Cyperus, Ipomoea and Xanthium.  91.  Methods of controlling undesirable vegetation comprising the step of applying a herbicidally effective amount of at least one mixture according to the forty-fourth modality in which the amount of the mixture is applied in a rate, expressed in gai / ha or gae / ha of terbuthylazine selected from the group of rates and rate ranges consisting of approximately: 60, 125, 250, 500, 1000, 1500, and 3000 within any defined range between any pair of the preceding values.  93.  Methods according to the forty-fourth or ninety-first modalities in which the controlled plant is at least one plant selected from the group consisting of: XANST, yet other modalities include control of plants of the genera consisting of: Xanthium.  94.  The composition of modality 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is atrazine.  95.  The composition of modality 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is bentazon-sodium.  96.  The composition of modality 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is bromoxynil.  97.  The composition of modality 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is chlorotoluron.  98.  The composition of modality 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is cyanazine.  99.  The composition of modality 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is diuron.  100.  The composition of modality 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is hexazonone.  101.  The composition of modality 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is ioxynil.  102.  The composition of modality 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is isopro-turon.  103.  The composition of modality 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is linuron.  104.  The composition of modality 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is methyl benzuron.  105.  The composition of modality 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is metri-buzin.  106.  The composition of modality 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is propanyl.  107.  The composition of modality 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is pyridate.  108.  The composition of modality 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is siduron.  109.  The composition of modality 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is simazine.  110.  The composition of modality 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b is symmetrical.  111.  The composition of modality 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is tebutiu-ron.  112.  The composition of modality 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is terbuti-lazine.  113.  The composition of embodiment 1, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to atrazine or agriculturally acceptable salt or ester thereof is approximately 1: 2240 to approximately 6: 1.  114.  The composition of embodiment 1, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to bentazon or agriculturally acceptable salt thereof is approximately 1: 1120 to approximately 3: 1.  115.  The composition of mode 1, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to bromoxynil or agriculturally acceptable salt thereof is approximately 1: 280 to approximately 12: 1.  116.  The composition of mode 1, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to chlorotoluron or agriculturally acceptable salt or ester thereof is approximately 1: 1750 to approximately 1.5: 1 .  117.  The composition of mode 1, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to cyanazine or agriculturally acceptable salt thereof is approximately 1: 2650 to approximately 6: 1.  118.  The composition of embodiment 1, wherein the weight ratio of the compound of the formula (I) or agriculturally acceptable salt or ester thereof to the agriculturally acceptable diuron thereof is approximately 1: 3600 to approximately 6: 1.  119.  The composition of embodiment 1, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to hexazinone or agriculturally acceptable salt thereof is from approximately 1: 2500 to approximately 12: 1.  120.  The composition of embodiment 1, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to ioxynil or agriculturally acceptable salt thereof is approximately 1: 200 to approximately 12: 1.  121.  The composition of mode 1, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to isoproturon or agriculturally acceptable salt thereof is from approximately 1: 750 to approximately 12: 1.  122.  The composition of embodiment 1, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to linuron or agriculturally acceptable salt thereof is approximately 1: 2250 to approximately 6: 1.  123.  The composition of mode 1, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to metibenzuron or agriculturally acceptable salt thereof is approximately 1: 1400 to approximately 4: 1.  124.  The composition of mode 1, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to metribuzin or agriculturally acceptable salt thereof is approximately 1: 2800 to approximately 6: 1.  125.  The composition of mode 1, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to propanyl or agriculturally acceptable salt thereof is approximately 1: 2800 to approximately 1: 1.  126.  The composition of embodiment 1, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to pyridate or agriculturally acceptable salt thereof is approximately 1: 800 to approximately 12: 1.  127.  The composition of embodiment 1, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to siduron or agriculturally acceptable salt thereof is approximately 1: 4500 to approximately 2: 1.  128.  The composition of embodiment 1, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to simazine or agriculturally acceptable salt thereof is approximately 1: 4250 to approximately 2: 1.  129.  The composition of embodiment 1, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to symmetry or agriculturally acceptable salt thereof is approximately 1: 1000 to approximately 12: 1.  130.  The composition of mode 1, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to tebutiuron or agriculturally acceptable salt thereof is approximately 1: 2240 to approximately 2: 1.  131.  The composition of embodiment 1, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to terbuthylazine or agriculturally acceptable thereof is approximately 1: 1500 to approximately 3: 1.  132.  The composition of any of modalities 94 to 131 which is synergistic as determined by Colby's equation.  Herbicide compositions comprising and methods of controlling undesirable vegetation using a herbicidally effective amount of (a) a compound of formula (I) or an agriculturally acceptable salt or ester thereof and (b) a PS II inhibitor are provided in this application selected from the group consisting of: atrazine, ben-tazon, bentazon-sodium, bromoxynil, bromoxynil octanoate, chlorotoluron, cyano-zine, diuron, hexazinone, ioxynil, isoproturon, linuron, metibenzuron, metribu-zin, propanil, pyridate , simazine, symmetrine, tebutiuron and terbuthylazine, or derivatives, for example, salt or ester thereof.  The compositions can also contain an agriculturally acceptable adjuvant or vehicle.  Detailed Description Definitions As used in this application, the compound of formula (I) has the following structure: The compound of formula (I) can be identified by the name 4-amino-3-chloro-6- (4-chloro-2- acid) fluorine-3-methoxyphenyl) -5-fluoropyridine-2-carboxylic and has been described in U.S. Patent. S.  7. 314. 849 (B2), which is incorporated in this application by reference in its entirety.  Exemplary uses of the compound of formula (I) include control of undesirable vegetation, including grass, broadleaved weeds and ciperaceae, in multiple situations of non-harvest and harvest.
Atrazine is 6-chloro-A / -ethyl- / V '- (1-methylethyl) -1,3,5-triazine-2,4-diamine. Its herbicidal activity is described in The Pesticide Manual, Fifte-enth Edition, 2009. Exemplary uses of atrazine include its use for post-emergence and pre-emergence control of broadleaf and grass weeds, for example, in corn, sorghum, lawn , sugar cane and other crops. Atrazine has the following structure: Bentazon is 3- (1-methylethyl) - // - / - 2,1,3-benzothiadiazin-4 (3H) -one 2,2 dioxide. Its herbicidal activity is described in The Pesticide Manual, Fifteen-th Edition, 2009. It is also known as bentazone. Bentazon was used as its sodium salt, sodium bentazon. Exemplary uses of bentazon include its use for the control of broadleaf and cyperaceous weeds in grass and broadleaf cultures. Bentazon has the following structure: Bromoxynil is 3,5-dibromo-4-hydroxybenzonitrile. Its herbicidal activity is described in The Pesticide Manual, Fifteenth Edition, 2009. Bromoxynil was used as its octanoate ester, bromoxynil octanoate. E-xemplar uses of bromoxynil include its use for post-emergence control of broadleaf weeds, for example, in cereals, ryegrass seed crops, lawn, corn and sorghum. It has the following structure: Chlorotoluron is / V- (3-chloro-4-methylphenyl) - / /, / / - dimethylurea. Its herbicidal activity is described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of chlorotoluron include its use for the control of broadleaf weeds and grasses, for example, in winter cereals. It has the following structure: Cyanazine is 2 - [[4-chloro-6- (ethylamino) -1,3,5-triazin-2-yl] amino] -2-methylpropanonitrile. Its herbicidal activity is described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of cyanazine include its use for the pre-emergence control of weeds in beans, corn and peas and post-emergence control of weeds in early barley and wheat . It has the following structure: Diuron is A / ’- (3,4-dichlorophenyl) -A /, A / -dimethylurea. Its herbicidal activity is described in The Pesticide Manual, Fifteenth Edition, 2009. E-xemplar uses of diuron include its use for post-emergence and pre-emergence control of broadleaved weeds and grasses in, for example, corn, sorghum, sugar cane, citrus and other crops. Diuron has the following structure: Hexazinone is 3-cyclohexyl-6- (dimethylamino) -1-methyl-1,3,5-triazine-2,4 (1H, 3H) -dione. Its herbicidal activity is described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of hexazinone include its use for the post-emergence control of annual, biennial and perennial weeds in alfalfa, pineapples, sugar cane and conifers. It has the following structure: loxynil 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 the post-emergence control of annual broadleaf weeds in cereals, onions, leeks, garlic, chalo-tas, flax, sugar cane, forage grams, lawns and recently sown lawn. It has the following structure: Isoproturon is / V, / V-ó / mef // - / V44- (1-methylethyl) phenyl] urea. Its herbicidal activity is described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of isoproturon include its use for pre- and post-emergence control of annual grass and annual broadleaf weeds, for example, in spring and winter wheat. winter, spring and winter barley, winter rye and triticale. It has the following structure: Linuron is A / - (3,4-dichlorophenyl) -A / -methoxy - / / - methylurea. Its herbicidal activity is described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of linuron include its use for pre- and post-emergence control of annual and broadleaf grass weeds, as well as perennial weeds in asparagus seedlings, artichokes, carrots, parsley, fennel, parsnips, herbs and spices, celery, horseradish, onions, leeks, garlic, potatoes, peas, fava beans, soybeans, cereals, corn, sorghum, cotton, flax, sunflowers, cane sugar, ornamentals, established vines, bananas, cassava, coffee, tea, rice, peanuts, ornamental trees and shrubs and other crops. It has the following structure: Metibenzuron is / V-2-benzothiazolyl- / V, / V-dimethylurea. Metibenzu-ron is also known as metabenztiazuron. The herbicidal activity of metibenzuron is described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of metibenzuron include its use for the control of a broad spectrum of broadleaf and grass weeds, for example in cereals, vegetables, corn, garlic and onions. It has the following structure: Metribuzin is 4-amino-6- (1,1-dimethylethyl) -3- (methylthio) -1,2,4-triazin-5 (4H) -one. Its herbicidal activity is described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of metribuzin include its use for post-emergence and pre-emergence control of broadleaf weeds, for example, in soybeans, potatoes, corn, vegetables and others cultures. Metribuzin has the following structure: Propanil is A / - (3,4-dichlorophenyl) propanamide. Its herbicidal activity is described in The Pesticide Manual, Fifteenth Edition, 2009. e-Xemplar uses of propanil include its use for the post-emergence control of broadleaf weeds and grasses in, for example, rice. It has 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 broadleaf weeds and grass weeds, for example, in more, sweet corn, rapeseed, cereals, rice, peanuts and vegetables. It has the following structure: Siduron is / V- (2-methylcyclohexyl) - / V-phenylurea. Its herbicidal activity is described in The Pesticide Manual, Fifteenth Edition, 2009. e-xemplares uses of siduron include its use for the pre-emergence control of Digitaria spp. and annual grass weeds on, for example, lawn farms, grass seed production and established lawn. It has the following structure: Simazine is 6-chloro-N, 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 to control the germination of annual grass and broadleaf weeds in, for example, pome, prumoid, shrub and cane, citrus fruits, vines, strawberries, nuts, olives, pineapples, fava beans, beans, peas, plus, sweet corn, asparagus, hops, alfalfa, lupines, rapeseed, artichokes, sugar cane, cocoa, coffee, rubber, oil palm, tea, lawn and ornamentals. It has the following structure: Simetrina is A /, A / -d / ef // - 6- (methylthio) -1,3,5-triazine-2,4-diamine. Si-metrina is simetrin. Its herbicidal activity is described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of simetrin include its use for the control of broadleaf weeds, for example, in rice. It has the following structure: Tebutiuron is A / - [5- (1,1-dimethylethyl) -1,3,4-thiadiazol-2-yl] -A /, / / - dimethylurea. Its herbicidal activity is described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of tebutiuron include its use for the control of herbaceous and woody plants, annual weeds and many perennial grasses and unwanted woody plants in pastures and natural pasture and control of grass and broadleaved weeds in sugar cane. It has the following structure: Terbuthylazine is 6-chloro-A / - (1,1-dimethylethyl) - / V-ethyl-1,3,5-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, for example, in corn, sorghum, vines, fruit trees, citrus, coffee, oil palm, cocoa, olives, potatoes, peas, beans, sugar cane, rubber and forestry (tree nurseries and new plantations). It has the following structure: As used in this application, the herbicide means a compound, for example, an active ingredient that eliminates, controls, or otherwise adversely modifies the growth of plants.
As used in this application, herbicidally effective or vegetation control quantity is an amount of the active ingredient that causes an effect that adversely modifies vegetation, for example, causing deviations from natural development, elimination, affecting regulation, causing desiccation, causing the delay, and the like.
As used in this application, controlling undesirable vegetation means preventing, reducing, eliminating or otherwise adversely modifying the development of plants and vegetation. Described in this application are methods of controlling undesirable vegetation by applying certain combinations of herbicide or compositions. Application methods include, but are not limited to, applications to the vegetation or locus thereof, for example, application to the area adjacent to the vegetation, as well as pre-emergence, post-emergence, leaf applications (diffused, directed, banded, punctual , mechanical, superior or rescue), and in water (vegetation emerged and submerged, diffused, punctual, mechanical, injected in water, granular, punctual granular, agitated flask or spray flow) through methods of manual application, backpack, machine, tractor or aerial (plane and helicopter).
As used in this application, plants and vegetation include, but are not limited to, germinating seeds, emerging seedlings, plants that emerge from vegetative propagules, immature vegetation and established vegetation.
As used in this application, agriculturally acceptable salts and esters refer to salts and esters that exhibit herbicidal activity, or that are or can be converted into plants, water or soil to the herbicide referred to. Exemplary agriculturally acceptable esters are those that are or can be hydrolyzed, oxidized, metabolized, or otherwise converted, for example, in plants, water or soil, to the corresponding carboxylic acid which, depending on the pH, may be in dissociated form or not dissociated.
Exemplary salts include those derived from alkali or alkaline earth metals and those derived from ammonia and amines. Exemplary cations include sodium, potassium, magnesium and amine cations of the formula: where R1, R2, R3 and R4 each independently represent 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. In addition, any two of R1, R2, R3 and R4 together can represent an aliphatic difunctional moiety that contains one to twelve carbon atoms and up to two sulfur or oxygen atoms. Salts can be prepared by treatment with a metal hydroxide, such as sodium hydroxide, with an amine, such as ammonia, trimethylamine, diethanolamine, 2-methylthiopropylamine, bisalylamine, 2-butoxyethylamine, morpholine, cyclododecylamine, or benzylamine or with a hydroxide tetraalkylammonium, such as tetramethylammonium hydroxide or choline hydroxide.
Exemplary esters include C1-C12 alkyl derivatives, C3-C12 alkenyl, C3-C12 alkynyl or C7-C10 alkyl alcohols substituted by aryl, such as methyl alcohol, isopropyl alcohol, 1-butanol, 2-ethylhexanol, bu-toxiethanol , methoxypropanol, allyl alcohol, propargyl alcohol, cyclohexanol or benzyl alcohols not substituted or substituted. Benzyl alcohols can be substituted by 1 to 3 substituents independently selected from halogen, C1-C4 alkyl or C1-C4 alkoxy. Esters can be prepared by coupling acids with 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 alkyl halides or alkyl sulfonates in the presence of a base such as triethylamine or lithium carbonate; by reacting the corresponding acid chloride of an acid with an appropriate alcohol; by reacting the corresponding acid with an appropriate alcohol in the presence of an acid catalyst or by transesterification.
Compositions and Methods Herbicide compositions comprising an herbicidally effective amount of (a) a compound of formula (I) or an agriculturally acceptable salt or ester thereof and (b) a PS II inhibitor selected from the group consisting of in atrazine, ben-tazon, bentazon-sodium, bromoxynil, bromoxynil octanoate, chlorotoluron, cyanozine, diuron, hexazinone, ioxynil, isoproturon, linuron, metibenzuron, metribu-zin, propanil, pyridate, siduretron, syurebon, sima terbuthylazine, or a salt or ester thereof. Also provided in this application are the methods of controlling undesirable vegetation which includes contact of the vegetation or the locus thereof, that is, the area adjacent to the undesirable vegetation, or application to the soil or water to prevent the appearance or growth of the vegetation of an herbicidically effective amount of the compound of formula (I) or an agriculturally acceptable salt 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, metibenzuron, metribuzin, propanil, pyridate, siduron, simazine, symmetrine, tebutiuron and terbutilazine, or a salt or ester thereof. In certain embodiments, the methods employ the compositions described in this application.
In addition, in some embodiments, the combination of compound (I) or an agriculturally acceptable salt or ester thereof and a PS II inhibitor or an agriculturally acceptable salt or ester thereof exhibits synergy, for example, the herbicidal active ingredients are more effective in combination than when applied individually. The Weed Science Society of America Herbicide Handbook, Ninth Edition, 2007, p. 429 note that "‘ synergy ’[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 Colby's equation. Colby, S.R. 1967. Calculation of the synergistic and antagonistic response of herbicide combi-nations. Weeds 15: 20-22.
In certain embodiments of the compositions and methods described in this application, the compound of formula (I), i.e., carboxylic acid, is employed. In certain embodiments, a carboxylate salt of the compound of formula (I) is employed. In certain embodiments, an aralkyl or alkyl ester is employed. In certain embodiments, benzyl, substituted benzyl or C1-4 alkyl, for example, the n-butyl ester is employed. In certain embodiments, the benzyl ester is used.
In some embodiments, the compound of formula (I) or salt or ester thereof and a PS II inhibitor, or an agriculturally acceptable salt or ester thereof are formulated in a composition, mixing tank, applied simultaneously or applied sequentially. Herbicidal activity is exhibited by the compounds when they are applied directly to the plant or to the plant's locus at any stage of growth. The observed effect depends on the plant species to be controlled, the plant's growth stage, the applied dilution parameters and spray droplet size, the particle size of solid components, the environmental conditions at the time of use, the specific compound employed, the specific adjuvants and vehicles employed, type of soil, and the like, as well as the amount of chemical applied. These and other factors can be adjusted to promote non-selective or selective herbicidal action. In some embodiments, the compositions described in this application are applied as a post-emergence application, pre-emergence application, or water application in flooded rice fields or bodies of water (for example, ponds, lakes and streams), to relatively undesirable vegetation immature to achieve maximum weed control.
In some embodiments, the compositions and methods provided in this application are used to control weeds in crops, including but not limited to rice directly sown, sown in water and transplanted, cereals, wheat, barley, oats, rye, sorghum, corn, sugar cane, sunflower, rapeseed, canola, beet, soy, cotton, pineapple, pasture, pasture, natural pasture, fallow, lawn, tree and vine orchards, aquatic, plantation crops, vegetables , management of industrial vegetation (IVM) and easements (ROW).
In certain embodiments, the compositions and methods provided in this application are used to control weeds in rice. In certain modalities, rice is directly sown, sown in water, or transplanted rice.
The compositions and methods described in this application can be used to control undesirable vegetation in cultures tolerant to glyphosate, tolerant to the 5-enolpyruvylshikimato-3-phosphate synthase (EPSP) inhibitor, tolerant to glufosinate, tolerant to the glutamine inhibitor -tase, tolerant to dicamba, tolerant to phenoxy auxin, tolerant to pyridyloxy auxin, tolerant to auxin, tolerant to auxin transport inhibitor, tolerant to aryloxyphenoxypropionate, tolerant to cyclohexanedione, tolerant to phenylpyrazoline, tolerant to acetyl CoA carboxylase inhibitor ( ACCase), imidazolinone tolerant, sulfonylurea tolerant, pyrimidinyl thiobenzoate tolerant, triazolopyrimidine tolerant, sulfonylaminocarbon-niltriazolinone tolerant, tolerant to acetolactate synthase (ALS) inhibitor or acetohydroxy acid inhibitor (4) hydroxyphenyl-pyruvate dioxigenase (HPPD), tolerant to the desaturated phytoene inhibitor rase, tolerant to carotenoid biosynthesis inhibitor, tolerant to protoporphyrinogen oxidase inhibitor (PPO), tolerant to cellulose biosynthesis inhibitor, tolerant to mitosis inhibitor, tolerant to microtubule inhibitor, tolerant to fatty acid inhibitor very long, tolerant to fatty acid and lipid biosynthesis inhibitor, tolerant to photosynthesis inhibitor I, tolerant to photosystem inhibitor II, tolerant to triazine and tolerant to bromoxynil (such as, but not limited to soy, cotton, pipe it / rapeseed, rice, cereals, corn, sorghum, sunflower, beet, sugar cane, lawn, etc.). For example, in conjunction with glyphosate, EPSP synthase inhibitors, glufosinate, glutamine synthase inhibitors, dicamba, phenoxy auxins, pyridyloxy auxins, synthetic auxins, au- xine transport inhibitors, aryloxyphenoxypropionates, ACCase inhibitors, cyclohexanodiones , phenylpyrazolines, imidazolinones, sulfonylureas, pyrimidinylthiobenzoates, triazo-lopyrimidines, sulfonylaminocarbonyltriazolinones, ALS or AHAS inhibitors, HPPD inhibitors, phytene desaturations inhibitors, carotenoid biosynthesis inhibitors, carotenoid inhibitors, inhibitors of carotenoids mitosis, 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 can be used to control undesirable vegetation in crops that have multiple or stacked traits, giving tolerance to multiple chemicals and / or inhibitors of multiple modes of action.
In some embodiments, the compound of formula (I) or salt or ester thereof and complementary herbicide or salt or ester thereof is used in combination with herbicides that are selective for the crop being treated and that complete the spectrum of controlled weeds by these compounds at the application rate employed. In some embodiments, the compositions described in this application and other complementary herbicides are applied at the same time, as a combination formulation or as a tank mixture, or sequentially.
The compositions and methods can be used in the control of undesirable vegetation in crops that have tolerance to a-gronomic stress (including but not limited to drought, cold, heat, salt, water, nutrients, fertility, pH), tolerance to pests ( including but not limited to insects, fungi and pathogens) and traits of crop improvement (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 in this application are used to control undesirable vegetation. Undesirable vegetation includes, but is not limited to, undesirable vegetation that occurs in rice, cereals, wheat, barley, oats, rye, sorghum, corn / maize, sugar cane, sunflower, rapeseed, canola, beet, soy, cotton, pineapple, pasture, pasture, natural pasture, fallow, lawn, tree and vine orchards, aquatic, plantation crops, vegetables, industrial vegetation management (IVM) and easements (ROW).
In some embodiments, the methods provided in this application are used to control undesirable vegetation in rice. In certain embodiments, the undesirable vegetation is Brachiaria platyphylla (Groseb). Nash or Urochloa platyphylla (Nash) R.D. Webster (broadleaf brachiaria grass, BRAPP), Digitaria sanguinalis (L). Scop. (large mattress grass, DIGSA), Echinochloa species (ECHSS), Echinochloa crus-galli (L). P. Beauv. (ca-pim-capybara, ECHCG), Echinochloa crus-pavonis (Kunth) Schult. (rice grass, ECHCV), Echinochloa colonum (L). LINK (jaú grass, ECHCO), Echinochloa oryzoides (Ard). Fritsch (early watergrass, ECHOR), Echinochloa oryzicola (Vasinger) Vasinger (late watergrass, ECHPH), Echinochloa phyl-lopogon (Stapf) Koso-Pol. (capybara grass, ECHPH), Echinochloa polystachya (Kunth) Hitchc. (beach grass, ECHPO), Ischaemum rugosum Salisb. (male grass, ISCRU), Leptochloa chinensis (L). Nees (Chinese spring top, LEFCH), Leptochloa fascicularis (Lam). Gray (grass-fat, LEFFA), Leptochloa panicoides (Presl). Hitchc. (Amazon spring top, LEFPA), Oryza species (red and weed rice, ORYSS), Panicum dichotomiflorum (L). Michx. (swamp grass, PANDI), Paspalum dilatatum Poir. (honeygrass, PASDI), Rottboellia cochinchinen-sis (honeygrass). W.D. Clayton (camalote grass, ROOEX), Cy-turkey species (CYPSS), Cyperus difformis L. (junquinho, CYPDI), Cyperus dubius Rottb. (MAPDU), Cyperus esculentus L. (yellow sedge, CYPES), Cyperus would L. (marsh sedge, CYPIR), Cyperus rotundus L. (purple tiririca, CY-PRO), Cyperus serotinus Rottb./CBCIarke (red tiririca , CYPSE), Eleocharis species (ELOSS), Fimbristylis miliacea (L). Vahl (false cumin, FIMMI), Schoenoplectus species (SCPSS), Schoenoplectus juncoides Roxb. (Button junco, SCPJU), Bolboschoenus maritimus (L). Palia or S-choenoplectus maritimus L. Lye (garlicgrass, SCPMA), Schoenoplectus mu-cronatus L. (rice paddy, SCPMU), Aeschynomene species, (jointvetch, AESSS), Alternanthera philoxeroides (Mart). Griseb. (alternanthera, ALRPH), Alisma plantago-aquatica L. (common alisma, ALSPA), Amaranthus species, (carurus and amaranth, AMASS), Ammannia coccinea Rottb. (redstem, AMM-CO), Commelina benghalensis L. (trapoeraba, COMBE), Eclipta alba (L). Hassk. (Buttonweed, ECLAL), Heteranthera limosa (SW). Willd.A / ahl (open grass, HETLI), Heteranthera reniformis R. & P. (marsh cress, HETRE), Ipomoea species (ipomeias, IPOSS), Ipomoea hederacea (L). Jacq. (viola string, IPOHE), Lindernia dubia (L). Pennell (low false morass, LIDDU), Ludwigia species (LUDSS), Ludwigia linifolia Poir. (Maltese cross, LUDLI), Ludwigia octovalvis (Jacq). Raven (ludwigia, LUDOC), Monochoria korsakowii Regei & Maack (monorail, MOOKA), Monochoria vaginalis (Burm. F.) C. Presl ex Kuhth, (monorail, MOOVA), Murdannia nudiflora (L). Brenan (trapoerabinha, MUDNU), Polygonum pensylvanicum L., (Pennsylvania smartweed, POLPY), Polygonum persicaria L. (ladysthumb, POLPE), Polygonum hydropiperoides Michx. (POLHP, mild smartweed), Ro-tala indica (Willd). Koehne (Rotala indica, ROTIN), Sagittaria species, (arrowhead, SAGSS), Sesbania exaltata (Raf). Cory / Rydb. Ex Hill (sesbania hemp, SEBEX), or Sphenoclea zeylanica Gaertn. (gooseweed, SPDZE).
In some embodiments, the methods provided in this application are used to control undesirable vegetation on cereals. In certain embodiments, the undesirable vegetation is Alopecurus myosuroides Huds. (field fox-tailed fox, ALOMY), Apera spica-venti (L). Beauv. (silky-feather grass, APESV), Avena fatua L. (wild oats, AVEFA), Bromus tectorum L. (barley grass, BROTE), Lolium multiflorum Lam. (ryegrass, LOLMU), Phalaris Retz minor, (talaceiro, PFIAMI), Poa annua L. (winter pasture, POANN), Setaria pumila (Poir). Roemer & J.A. Schul-tes (capintinga, SETLU), Setaria viridis (L). Beauv. (green grass, SETVI), Amaranthus retroflexus L. (giant caruru, AMARE), Brassica species (BRSSS), Chenopodium album L. (white anarch, CFIEAL), Cirsium ar-vense (L). Scop. (Canada thistle, CIRARJ, Galium aparine L. (aparina, GALAP), Kochia scoparia (L). Schrad. (Kochia, KCFISC), Lamium purpureum L. (purple lamina, LAMPU), Matricaria recutita L. (chamomile, MATCFI ), Matrica-ria matricarioides (Less.) Porter (wild chamomile, MATMT), Papaver rhoeas L. (common poppy, PAPRH), Polygonum convolvulus L. (wild buckwheat, POLCO), Salsola tragus L. (Russian thistle, SASKR) , Sina-pis species (SINSS), Sinapis arvensis L. (wild mustard, SINAR), Stellaria media (L). Vill. (morugem, STEME), Veronica Persian Poir. (Veronica da Persia, VERPE), Viola arvensis Murr. (field violet, VIOAR), or Viola tricolor L. (wild violet, VIOTR).
In some modalities, the methods provided in this application are used to control undesirable vegetation in range and pasture, fallow, IVM and ROW. In certain modalities, the undesirable vegetation is Ambrosia artemisiifolia L. (common snail, AMBEL), Cassia obtusifolia (sickle pod, CASOB), Centaurea maculosa auct. not Lam. (spotted cornflower, CENMA), Cirsium arvense (L). Scop. (Canada thistle, Cl-RAR), Convolvulus arvensis L. (bell, CONAR), Daucus carota L. (wild carrot, DAUCA), Euphorbia esula L. (leafy spurge, EPHES), Lactuca serriola L./Torn. (wild lettuce, LACSE), Plantago lanceolata L. (tancha-gem, PLALA), Rumex obtusifolius L. (cow-tongue, RUMOB), Sida spinosa L. (thorn guanxuma, SIDSP), Sinapis arvensis L. (wild mustard, SINAR), Sonchus arvensis L. (milkweed, SONAR), Solidago species (solida-go, SOOSS), Taraxacum offícinale GH Weber ex Wiggers (dandelion, TAROF), Trifolium repens L. (white clover, TRFRE), or Urtica dioica L. (nettle, URTDI).
In some embodiments, the methods provided in this application are used to control the undesirable vegetation found in row crops, tree and vine crops and perennial crops. In certain embodiments, the undesirable vegetation is Alopecurus myosuroides Huds. (field fox-tail grass, ALOMY), Avena fatua L. (wild oats, A-VEFA), Brachiaria decumbens Stapf. or Urochloa decumbens (Stapf) R.D. Webster (brachiaria, BRADC), Brachiaria brizantha (Flochst. ex A. Rich.) Stapf. or Urochloa brizantha (Flochst. ex A. Rich.) R.D. (broom grass, BRABR), Brachiaria platyphylla (Groseb). Nash or Urochloa platyphylla (Nash) R.D. Webster (broadleaf brachiaria grass, BRAPP), Brachiaria plantagi-nea (Link) Hitchc. or Urochloa plantaginea (Link) R.D. Webster (sweet grass, BRAPL), Cenchrus echinatus L. (sweet grass, CENEC), Digitaria horizon-talis Willd. (Jamaican mattress grass, DIGHO), Digitaria insularis (L). Mez ex Ekman (sourgrass, TRCIN), Digitaria sanguinalis (L). Scop. (large mattress grass, DIGSA), Echinochloa crus-galli (L). P. Beauv. (capybara grass, E-CHCG), Echinochloa colonum (L). Link (jaú grass, ECHCO), Eleusine indica (L). Gaertn. (crowfoot grass, ELEIN), Lolium multiflorum Lam. (Azevém, LOLMU), Panicum dichotomiflorum Michx. (wet grass, PANDI), Pa-nicum miliaceum L. (wild millet, PANMI), Setaria faberi Herrm. (fox-tailed grass, SETFA), Setaria viridis (L). Beauv. (green grass, SETVI), Sorghum halepense (L). Pers. (Johnsongrass, SORHA), Sorghum bicolor (L). Mo-ench ssp. Arundinaceum (shattercane, SORVU), Cyperus esculentus L. (yellow tiririca, CYPES), Cyperus rotundus L. (purple tiririca, CYPRO), Abu-tilon theophrasti Medik. (jute-da-china, ABUTH), Amaranthus species (caru-rus and amarantos, AMASS), Ambrosia artemisiifolia L. (common hedge, AM-BEL), Ambrosia psilostachya DC. (western hull, AMBPS), Ambrosia trifida L. (giant hull, AMBTR), Anoda cristata (L). Schlecht. (esoda poroda, ANVCR), Asclepias syriaca L. (milky chaff, ASCSY), Bidens pilosa L. (black pick, BIDPI), Borreria species (BOISS), Borreria alata (Aubl). A.D. or Spermacoce alata Aubl. (hot grass, BOILF), Spermacose latifolia (po-aia-da-praia, BOILF), Chenopodium album L. (white anch, CHEAL), Cirsium arvense (L). Scop. (Canada thistle, CIRAR), Commelina bengha-lensis L. (tropical cornflower, COMBE), Datura stramonium L. (trumpet, DATST), Daucus carota L. (wild carrot, DAUCA), Euphorbia hetero-phylla L. (poinsetia EPHHL), Euphorbia hirta L. or Chamaesyce hirta (L). Millsp. (Santa Luzia herb, EPHHI), Euphorbia dentata Michx. (toothed spurge, EPHDE), Erigeron bonariensis L. or Conyza bonariensis (L). Cronq. (avoadinha, ERIBO), Erigeron canadensis L. or Conyza cana-densis (L). Cronq. (Canadian avoadinha, ERICA), Conyza sumatrensis (Retz). E. H. Walker (avocado ivory, ERIFL), Helianthus annuus L. (common sunflower, HELAN), Jacquemontia tamnifolia (L). Griseb. (small morning glory, IAQTA), Ipomoea hederacea (L). Jacq. (viola-string, IPOHE), / -pomoea lacunosa L. (white morning glory, IPOLA), Lactuca serriola L./Torn. (wild-faced, LACSE), Portulaca oleracea L. (purslane, POROL), Richardia species (pusley, RCHSS), Sida species (sida, SIDSS), Sida spinosa L. (thorn guanxuma, SIDSP), Sinapis arvensis L. (wild mustard, SINAR), Solanum ptychanthum Dunal (eastern black nightshade, SOLPT), Tridax procumbens L. (bull herb, TRQPR), or Xanthium strumarium L. (broom, XANST).
In some embodiments, the methods provided in this application are used to control undesirable vegetation on the lawn. In certain modalities, the undesirable vegetation is Bellis perermis L. (English daisy, BELPE), Cyperus esculentus L. (yellow sedge, CYPES), Cy-turkey species (CYPSS), Digitaria sanguinaiis (L). Scop. (large mattress grass, DIGSA), Diodia virginiana L. (buttonweed, DIQVI), Euphorbia species (spurge, EPHSS), Glechoma hederacea L. (terrestrial ivy, GLEHE), Hydro-cotyle umbellata L. (dollarweed, HYDUM), Kyllinga species (kyllinga, K-YLSS), Lamium amplexicaule L. (henbit, LAMAM), Murdannia nudiflora (L). Brenan (trapoerabinha, MUDNU), Oxalis species (woodsorrel, OXASS), Plantago major L (broadleaf plantain, PLAMA), Plantago lanceolata L. (banana plantain, PLALA), Phyllanthus urinaria L. (stone breaker, PYLTE), Rumex obtusifolius L. (cow-tongue, RUMOB), Stachys floridana Shuttlew. (Florida concrete, STAFL), Stellaria media (L). Vill. (morugem, STEME), Taraxacum offícinale G.FI. Weber ex Wiggers (dandelion, TA-ROF), Trifolium repens L. (white clover, TRFRE), or Viola species (wild violet, VIOSS).
In some embodiments, the compositions and methods provided in this application are used to control undesirable vegetation consisting of grass, broadleaved weeds and cyperaceae. In certain embodiments, the compositions and methods provided in this application are used to control undesirable vegetation including species Abutilon, Amaranthus, Brachiaria or Urochloa, Brassica, Chenopodium, Commelina, Cyperus, Echinochloa, Fimbristylis, Galium, Ipomoea, Kochia, Lamium, Lep -tochloa, Salsola, Setaria, Sinapis, Verônica, Xanthium, Bolboschoenus, S-choenoplectus, Sinapis, Verônica and Xanthium.
In some embodiments, the combination of compound (I) is either an agriculturally acceptable ester or salt thereof and a PS II inhibitor or an agriculturally acceptable salt or ester thereof is used to control Abutilon theophrasti Medik. (jute-da-china, ABUTH), Amaranthus retroflexus L. (giant caruru, AMARE), Brachiaria platyphylla (Groseb). Nash or Uroc-hloa platyphylla (Nash) RD Webster (latifoliate brachiaria grass, BRAPP), Brassica napus L. (rapeseed, BRSNW), Chenopodium album L. (white anch, CHEAL), Commelina benghalensis L. (trapoeraba, COMBE), Cyperus would L. (marsh sedge, CYPIR), Cyperus rotundus L. (purple sedge, CYPRO), Echinochloa crus-galli (L). Beauv. (capybara grass, ECHCG), Echinochloa colona (L). Link (jaú grass, ECHCO), Echinochloa oryzoides (Ard). Fritsch (early watergrass, ECHOR), Fimbristylis miliacea (L). Vahl (false cumin, FIMMI), Galium aparine L. (aparina, GALAP), Ipomoea hederacea Jacq. (viola string, IPOHE), Kochia scoparia (L). Schrad. (kochia, KCFISC), La-mium purpureum L. (purple lamina, LAMPU), Leptochloa chinensis (L). Nees (Chinese spring top, LEFCH), Bolboschoenus maritimus (L). Palia or Schoenoplectus maritimus (L). Bleach (garlic grass, SCPMA), Salsola tragus L. (Russian thistle, SASKR), Setaria faberi Herrm. (fox-tailed grass, SETFA), Setaria viridis (L). Beauv. (green grass, SETVI), Sinapis arvensis L. (wild mustard, SINAR), and Veronica Persian Poir. (Veronica da Persia, VERPE), and Xanthium strumarium L. (burr, XANST).
The compounds of formula I or an agriculturally acceptable salt or ester thereof can be used to control herbicide resistant or tolerant weeds. The methods employing the combination of a compound of formula I or an agriculturally acceptable salt or ester thereof and the compositions described in this application can also be employed to control herbicide resistant or tolerant weeds. Exemplary resistant or tolerant weeds include, but are not limited to, biotypes resistant to or tolerant to acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors (e.g., imidazolinones, sulfonylureas, pyrimidinylthiobenzoates, triazolopyrimidines, sulfonylaminaminols) , photosystem II inhibitors (e.g., phenylcarbamates, pyridazinones, triazines, triazinones, uracils, amides, urea, benzothiadiazines, nitriles, phenylpyridazines), acetyl CoA carboxylase (ACCase) inhibitors (e.g., aryloxyphenyloxypropionates, hexyloxyphenionylpropionates phenylpyrazolines), synthetic auxins, (eg benzoic acids, phenoxycarboxylic acids, pyridine carboxylic acids, quinoline carboxylic acids), auxin transport inhibitors (eg phthalates, semicarbazones), photosystem I inhibitors (eg bipyridyls ), 5-enolpyruvylshikimato-3-phosphate synthase (EPSP) inhibitors, (for example o, glyphosate), glutamine synthetase inhibitors (eg, glufosinate, bialaphos), microtubule assembly inhibitors, (eg, benzamides, benzoic acids, dinitroanilines, phosphoramidates, pyridines), mitosis inhibitors (for example, carbamates ), very long-chain fatty acid (VLC-FA) inhibitors (eg acetamides, chloroacetamides, oxyacetamides, tetrazolines), fatty acid and lipid synthesis inhibitors (eg phosphorodithiates, thiocarbamates, benzofurans, chlorocarbonic acids), protoporphyrinogen oxidase (PPO) inhibitors (for example, diphenylethers, N-phenylphthalimides, oxadiazoles, oxazolidinediones, phenylpyrazoles, pyrimidindiones, thiadiazoles, triazolinones), carotenozide, amidone, and xoxinone biosynthesis inhibitors, by and ), phytene desaturase (PDS) inhibitors (eg, amides, anilidex, furanones, phenoxybutan-amides, pyri-diazinones, pyridines), 4-hydroxyphenyl-pyruvate dioxigen inhibitors if (HPPD) (for example, calistemones, isoxazoles, pyrazoles, tricetones), cellulose biosynthesis inhibitors (for example, nitriles, benzamides, quinclo-rac, triazolocarboxamides), herbicides with multiple modes of action such as quinclorac and herbicides not classified as arylaminopropionic acids, difenzoquat, endothall, and organoarsenic acids. Exemplary resistant or tolerant weeds include, but are not limited to, biotypes with resistance or tolerance to multiple herbicides, biotypes with resistance or tolerance to multiple chemical classes, biotypes with resistance or tolerance to multiple modes of herbicide action and biotypes with multiple tolerance or resistance mechanisms (eg target site resistance or metabolic resistance).
In some embodiments, an agriculturally acceptable ester or salt of bentazon is employed in the methods or compositions described in this application. In certain embodiments, bentazon sodium salt is used.
In some embodiments, an agriculturally acceptable ester or salt of ioxynil is employed in the methods or compositions described in this application. In certain embodiments, the sodium salt of ioxynil is used. In certain embodiments, the potassium salt of ioxynil is used. In certain embodiments, the ioxynil octanoate ester is used.
In some embodiments, an agriculturally acceptable ester or salt of bromoxynil is employed in the methods or compositions described in this application. In certain embodiments, the potassium salt of bromoxynil is used. In certain embodiments, the bromoxynil butyl ester is used. In certain embodiments, the bromoxynil heptyl ester is employed. In certain embodiments, the bromoxynil octanoate ester is used.
In certain embodiments of the compositions and methods described in this application, the compound of formula (I) or salt or ester thereof is used in combination with atrazine or salt thereof. As for the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to atrazine or salt thereof is within the range of approximately 1: 2200 to approximately 6: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to atrazine or salt thereof is within the range of 1: 509 to approximately 1: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to atrazine or salt thereof is within the range of approximately 1: 512 to approximately 1: 8. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to atrazine or salt thereof is within the range of approximately 1: 256 to approximately 1:16. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to atrazine or salt thereof is within the range of approximately 1: 256 to approximately 1: 9. In certain embodiments, the compositions provided in this application comprise the compound of formula (I) or its benzyl and atrazine ester or salt thereof. In one embodiment, the composition comprises the compound of formula (I) and atrazine or salt thereof, wherein the weight ratio of the compound of formula (I) to atrazine or salt thereof is approximately 1: 256 to approximately 1:32 . In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and atrazine or salt thereof, wherein the weight ratio of the benzyl ester of the compound of formula (I) to atrazine or salt thereof is approximately 1: 130 to approximately 1:16. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and atrazine or salt thereof, wherein the weight ratio of the benzyl ester of the compound of formula (I) to atrazine or salt thereof is approximately 1: 140 to approximately 1: 17.5. With respect to the methods, in certain modalities, the methods comprise contact of undesirable vegetation or locus thereof or application to the soil or water of a composition described in this application to prevent the appearance or growth of vegetation. In some embodiments, the composition is applied at an application rate of approximately 52 grams per hectare (g ai / ha) to approximately 4,700 g ai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of the active ingredient of approximately 60 grams per hectare (g ai / ha) to approximately 2,300 g ai / ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contact of undesirable vegetation or locus thereof or application to soil or water to prevent the appearance or growth of vegetation with a compound of formula (I) or salt or ester thereof and atrazine or salt thereof , for example, sequentially or simultaneously. In some embodiments, atrazine or salt thereof is applied at a rate of approximately 50 g ai / ha to approximately 4,400 g ai / ha and the compound of formula (I) of salt or ester thereof is applied at a rate of approximately 2 g ae / ha to approximately 300 g ae / ha. In some embodiments, atrazine or salt thereof is applied at a rate of approximately 140 g ai / ha to approximately 2,240 g ai / ha and the compound of formula (I) of salt or ester thereof is applied at a rate of approximately 2 g equivalent of acid per hectare (g ae / ha) to approximately 35 g ae / ha. In some embodiments, atrazine or salt thereof is applied at a rate of approximately 280 g ai / ha to approximately 1,120 g ai / ha and the compound of formula (I) of salt or ester thereof is applied at a rate of approximately 4 , 38 g equivalent of acid per hectare (g ae / ha) to approximately 35 g ae / ha. In certain embodiments, the methods use the compound of formula (I), or its benzyl and atrazine ester or salt thereof. In one embodiment, the methods use the compound of formula (I) and atrazine or salt thereof, where the compound of formula (I) is applied at a rate of approximately 4.38 g equivalent of acid per hectare (g ae / ha) at approximately 8.75 g ae / ha, and atrazine or salt thereof are applied at a rate of approximately 280 g ai / ha to approximately 1,120 g ai / ha. In one embodiment, the methods use the benzyl ester of the compound of formula (I) and atrazine or salt thereof, in which the benzyl ester of the compound of formula (I) is applied at a rate of approximately 4.38 g equivalents of acid per hectare (g ae / ha) to approximately 17.5 g ae / ha, and atrazine or salt thereof is applied at a rate of approximately 280 g ai / ha to approximately 560 g ai / ha. In one embodiment, the methods use the benzyl ester of the compound of formula (I) and atrazine or salt thereof, in which the benzyl ester of the compound of formula (I) is applied at a rate of a-approximately 8 g equivalents of acid per hectare (g ae / ha) to approximately 32 g ae / ha, and atrazine or salt thereof is applied at a rate of approximately 560 g ai / ha to approximately 1,120 g ai / ha. In certain embodiments, methods and compositions using the compound of formula (I) or salt or ester thereof in combination with atrazine or salt thereof are used to control BRAPP, CYPIR, ECHCG, XANST or E-CHCO.
In certain embodiments of the compositions and methods described in this application, the compound of formula (I) or salt or ester thereof is used in combination with bentazon or salt thereof. As for the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to bentazon or salt thereof is within the range of approximately 1: 1120 to approximately 3: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to bentazon or salt thereof is within the range of approximately 1: 256 to approximately 1: 1.2. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to bentazon or salt thereof is within the range of approximately 1: 192 to approximately 1: 3. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof is within the range of approximately 1:96 to approximately 1: 6. In certain embodiments, the compositions provided in this application 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 the formula (I) and bentazon-sodium, wherein the weight ratio of the compound of the formula (I) to bentazon-sodium is approximately 1:96 to approximately 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 of the compound of formula (I) to bentazon-sodium is approximately 1:96 a approximately 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 approximately 1:48 to approximately 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 approximately 1:13, 7 to approximately 1: 3.4. With respect to the methods, in certain modalities, the methods comprise contact of undesirable vegetation or locus thereof or application to the soil or water of a composition described in this application to prevent the appearance or growth of vegetation. In some embodiments, the composition is applied at an active ingredient application rate of approximately 107 grams per hectare (g ai / ha) to approximately 2,540 g ai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of the active ingredient of approximately 110 grams per hectare (g ai / ha) to approximately 1,205 g ai / ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contact of undesirable vegetation or locus thereof or application to soil or water to prevent the appearance or growth of vegetation with a compound of formula (I) or salt or ester thereof and bentazon or salt thereof , for example, sequentially or simultaneously. In some embodiments, bentazon or salt thereof is applied at a rate of approximately 105 g ai / ha to approximately 2,240 g ai / ha and the compound of formula (I) of salt or ester thereof is applied at a rate of approximately 2 g ae / ha to approximately 300 g ae / ha. In some embodiments, bentazon or salt thereof is applied at a rate of approximately 50 g ai / ha to approximately 2,240 g ai / ha and the compound of formula (I) of salt or ester thereof is applied at a rate of approximately 2 g equivalent of acid per hectare (g ae / ha) at approximately 140 g ae / ha. In some embodiments, bentazon or salt thereof is applied at a rate of approximately 60 g ai / ha to approximately 1,120 g ai / ha and the compound of formula (I) of salt or ester thereof is applied at a rate of approximately 4.38 g equivalent of acid per hectare (g ae / ha) to approximately 84.4 g ae / ha. In certain embodiments, the methods use the compound of the formula (I), or its benzyl or n-butyl ester and bentazon-sodium. In one embodiment, the methods use the compound of the formula (I) and bentazon-sodium, in which the compound of the formula (I) is applied at a rate of approximately 4.38 g equivalent of acid per hectare (g ae / ha) at approximately 84.8 g ae / ha, and bentazon-sodium is applied at a rate of approximately 105 g ai / ha to approximately 1,120 g ai / ha. In one embodiment, the methods use the benzyl ester of the compound of formula (I) and bentazon-sodium, in which the benzyl ester of the compound of formula (I) is applied at a rate of approximately 4.38 g equivalents of acid per hectare (g ae / ha) at approximately 70 g ae / ha, and bentazon-sodium is applied at a rate of approximately 105 g ai / ha to approximately 1,120 g ai / ha. In one embodiment, the methods use 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 approximately 17.5 g equivalents of acid per hectare (g ae / ha) at approximately 70 g ae / ha, and bentazon-sodium is applied at a rate of approximately 840 g ai / ha to approximately 1,120 g ai / ha. In one embodiment, the methods use 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 of approximately 8.75 g equivalent of acid per hectare (g ae / ha) at approximately 17.5 g ae / ha, and bentazon-sodium is applied at a rate of approximately 60 g ai / ha to approximately 120 g ai / ha. In certain embodiments, methods and compositions using the compound of formula (I) or salt or ester thereof in combination with bentazon or salt thereof are used to control BRSNW, COMBE, ECHCG, ECHOR, IPOHE, LEFCH, SCPMA or SETFA.
In certain embodiments of the compositions and methods described in this application, the compound of formula (I) or salt or ester thereof is used in combination with bromoxynil or salt thereof. As for the compositions, in some embodiments, the weight ratio of the compound of the formula (I) or salt or ester thereof to bromoxynil or salt thereof is within the range of approximately 1: 280 to approximately 12: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to bromoxynil or salt thereof is within the range of approximately 1: 254 to approximately 2: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to bromoxynil or salt thereof is within the range of approximately 1: 18a to approximately 1: 4. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and bromoxynil or salt thereof. With respect to the methods, in certain modalities, the methods comprise contact of undesirable vegetation or locus thereof or application to the soil or water of a composition described in this application to prevent the appearance or growth of vegetation. In some embodiments, the composition is applied at an application rate of approximately 27 grams per hectare (g ai / ha) to approximately 860 g ai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of the active ingredient of approximately 50 grams per hectare (g ai / ha) to approximately 610 g ai / ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contact of undesirable vegetation or locus thereof or application to soil or water to prevent the appearance or growth of vegetation with a compound of formula (I) or salt or ester thereof and bromoxynil or salt thereof , for example, sequentially or simultaneously. In some embodiments, bromoxynil or salt thereof is applied at a rate of approximately 25 g ai / ha to approximately 560 g ai / ha and the compound of formula (I) of salt or ester thereof is applied at a rate of approximately 2 g ae / ha to approximately 300 g a-elha. In certain embodiments, the methods use the compound of formula (I) or its benzyl or n-butyl ester and bromoxynil or salt thereof can be used to control AMARE, ECHCG, IPOHE or SETFA.
In certain embodiments of the compositions and methods described in this application, the compound of formula (I) or salt or ester thereof is used in combination with chlorotoluron or salt thereof. As for the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to chlorotoluron or salt thereof is within the range of approximately 1: 1750 to approximately 1.5: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to chlorotoluron or salt thereof is within the range of approximately 1: 909 to approximately 1: 4. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and chlorotoluron or salt thereof. With respect to the methods, in certain modalities, the methods comprise contact of undesirable vegetation or locus thereof or application to the soil or water of a composition described in this application to prevent the appearance or growth of vegetation. In some embodiments, the composition is applied at an application rate of the active ingredient of approximately 202 grams per hectare (g ai / ha) to approximately 3,800 g ai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of the active ingredient of approximately 203 grams per hectare (g ai / ha) to approximately 2,500 g ai / ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contact of undesirable vegetation or locus thereof or application to soil or water to prevent the appearance or growth of vegetation with a compound of formula (I) or salt or ester thereof and chlorotoluron or salt thereof , for example, sequentially or simultaneously. In some embodiments, chlorotoluron or its salt is applied at a rate of approximately 200 g ai / ha to approximately 3,500 g ai / ha and the compound of formula (I) of salt or ester thereof is applied at a rate of approximately 2 g ae / ha to approximately 300 g ae / ha. In certain embodiments, the methods use the compound of formula (I) or its benzyl or n-butyl ester and chlorotoluron or salt thereof.
In certain embodiments of the compositions and methods described in this application, the compound of formula (I) or salt or ester thereof is used in combination with cyanazine or salt thereof. As for the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to cyanazine or salt thereof is within the range of approximately 1: 2650 to approximately 6: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to cyanazine or salt thereof is within the range of approximately 1: 1600 to approximately 1: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to cyanazine or salt thereof is within the range of approximately 1: 110 to approximately 1: 5.3. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and cyanozine or salt thereof. With respect to the methods, in certain modalities, the methods comprise contact of undesirable vegetation or locus thereof or application to the soil or water of a composition described in this application to prevent the appearance or growth of vegetation. In some embodiments, the composition is applied at an application rate of the active ingredient of approximately 52 grams per hectare (g ai / ha) to approximately 5,600 g ai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of the active ingredient of approximately 53 grams per hectare (g ai / ha) to approximately 3,550 g ai / ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contact of undesirable vegetation or locus thereof or application to soil or water to prevent the appearance or growth of vegetation with a compound of formula (I) or salt or ester thereof and cyanazine or salt thereof , for example, sequentially or simultaneously. In some embodiments, cyanazine or salt thereof is applied at a rate of approximately 50 g ai / ha to approximately 5,300 g ai / ha and the compound of formula (I) of salt or ester thereof is applied at a rate of approximately 2 g ae / ha to approximately 300 g ae / ha. In some embodiments, cyanazine or salt thereof is applied at a rate of approximately 170 g ai / ha to approximately 880 g ai / ha and the compound of formula (I) of salt or ester thereof is applied at a rate of approximately 8 g ae / ha to approximately 32 g ae / ha. In certain embodiments, the methods use the compound of formula (I) or its benzyl or n-butyl ester and cyanazine or salt thereof for the control of BRAPP or IPOHE.
In certain embodiments of the compositions and methods described in this application, the compound of formula (I) or salt or ester thereof is used in combination with diuron or salt thereof. As for the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to diuron or salt thereof is within the range of approximately 1: 3600 to approximately 6: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to diuron or salt thereof is within the range of approximately 1: 509 to approximately 1: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to diuron or salt thereof is within the range of approximately 1:70 to approximately 1: 9. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and diuron or salt thereof. With respect to the methods, in certain modalities, the methods comprise contact of undesirable vegetation or locus thereof or application to the soil or water of a composition described in this application to prevent the appearance or growth of vegetation. In some embodiments, the composition is applied at an application rate of approximately 52 grams per hectare (g ai / ha) to approximately 7,500 g ai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of the active ingredient of approximately 55 grams per hectare (g ai / ha) to approximately 2,300 g ai / ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contact of undesirable vegetation or locus thereof or application to soil or water to prevent the appearance or growth of vegetation with a compound of formula (I) or salt or ester thereof and diuron or salt thereof , for example, sequentially or simultaneously. In some embodiments, diuron or salt thereof is applied at a rate of approximately 50 g ai / ha to approximately 7,200 g ai / ha and the compound of formula (I) of salt or ester thereof is applied at a rate of approximately 2 g ae / ha to approximately 300 g ae / ha. In some embodiments, diuron or salt thereof is applied at a rate of approximately 280 g ai / ha to approximately 1,120 g ai / ha and the compound of formula (I) of salt or ester thereof is applied at a rate of approximately 16 g ae / ha to approximately 32 g ae / ha. In certain modalities, the methods use the compound of formula (I) or its benzyl or n-butyl ester and diuron or salt thereof for the control of ABUTH, BRAPP, ECHCG, ECHCO, SETFA or SETVI.
In certain embodiments of the compositions and methods described in this application, the compound of formula (I) or salt or ester thereof is used in combination with hexazinone or salt thereof. As for the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to hexazinone or salt thereof is within the range of approximately 1: 2500 to approximately 12: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to hexazinone or salt thereof is within the range of approximately 1: 1360 to approximately 2: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to hexazinone or salt thereof is within the range of approximately 1: 156 to approximately 1:19. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and hexazinone or salt thereof. With respect to the methods, in certain modalities, the methods comprise contact of undesirable vegetation or locus thereof or application to the soil or water of a composition described in this application to prevent the appearance or growth of vegetation. In some embodiments, the composition is applied at an application rate of the active ingredient of approximately 27 grams per hectare (g ai / ha) to approximately 5,300 g ai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of the active ingredient of approximately 28 grams per hectare (g ai / ha) to approximately 3,050 g ai / ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contact of undesirable vegetation or locus thereof or application to soil or water to prevent the appearance or growth of vegetation with a compound of formula (I) or salt or ester thereof and hexazinone or salt thereof , for example, sequentially or simultaneously. In some embodiments, hexazinone or salt thereof is applied at a rate of approximately 25 g ai / ha to approximately 5,000 g ai / ha and the compound of formula (I) of salt or ester thereof is applied at a rate of approximately 2 g ae / ha to approximately 300 g ae / ha. In some embodiments, hexazinone or salt thereof is applied at a rate of approximately 625 g ai / ha to approximately 1,250 g ai / ha and the compound of formula (I) of salt or ester thereof is applied at a rate of approximately 8 g ae / ha to approximately 32 g ae / ha. In certain embodiments, the methods use the compound of formula (I) or its benzyl or n-butyl ester and hexazinone or salt thereof for the control of ECHCO, ECHCG or IPOHE.
In certain embodiments of the compositions and methods described in this application, the compound of formula (I) or salt or ester thereof is used in combination with ioxynil or salt thereof. As for the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to ioxynil or salt thereof is within the range of approximately 1: 200 to approximately 12: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to ioxynil or salt thereof is within the range of approximately 1: 136 to approximately 6: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to ioxynil or salt thereof is within the range of approximately 1:38 to approximately 1: 9. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and ioxynil or salt thereof. With respect to the methods, in certain modalities, the methods comprise contact of undesirable vegetation or locus thereof or application to the soil or water of a composition described in this application to prevent the appearance or growth of vegetation. In some embodiments, the composition is applied at an application rate of the active ingredient of approximately 27 grams per hectare (g ai / ha) to approximately 700 g ai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an active ingredient application rate of approximately 28 grams per hectare (g ai / ha) to approximately 450 g ai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and ioxynil or salt thereof. With respect to the methods, in certain modalities, the methods comprise contact of undesirable vegetation or locus thereof or application to the soil or water of a composition described in this application to prevent the appearance or growth of vegetation. In some embodiments, ioxynil or salt thereof is applied at a rate of approximately 25 g ai / ha to approximately 400 g ai / ha and the compound of formula (I) of salt or ester thereof is applied at a rate of approximately 2 g ae / ha to approximately 300 g ae / ha. In some embodiments, ioxynil or salt thereof is applied at a rate of approximately 300 g ai / ha to approximately 400 g ai / ha and the compound of formula (I) of salt or ester thereof is applied at a rate of approximately 8 g ae / ha to approximately 32 g ae / ha. In certain embodiments, the methods use the compound of the formula (I) or its benzyl or n-butyl ester and ioxynil or its salt to control IPOHE.
In certain embodiments of the compositions and methods described in this application, the compound of formula (I) or salt or ester thereof is used in combination with isoproturon or salt thereof. As for the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to isoproturon or salt thereof is within the range of approximately 1: 750 to approximately 12: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to isoproturon or salt thereof is within the range of approximately 1: 600 to approximately 1: 37.5. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to isoproturon or salt thereof is within the range of approximately 1: 455 to approximately 2: 1. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and isoproturon or salt thereof. With respect to the methods, in certain modalities, the methods comprise contact of undesirable vegetation or locus thereof or application to the soil or water of a composition described in this application to prevent the appearance or growth of vegetation. In some embodiments, the composition is applied at an application rate of the active ingredient of approximately 27 grams per hectare (g ai / ha) to approximately 1,800 g ai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of the active ingredient of approximately 28 grams per hectare (g ai / ha) to approximately 1,050 g ai / ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contact of undesirable vegetation or locus thereof or application to soil or water to prevent the appearance or growth of vegetation with a compound of formula (I) or salt or ester thereof and isoproturon or salt thereof , for example, sequentially or simultaneously. In some embodiments, the isoproturon or salt thereof is applied at a rate of approximately 25 g ai / ha to approximately 1,500 g ai / ha and the compound of formula (I) of salt or ester thereof is applied at a rate of approximately 2 g ae / ha to approximately 300 g ae / ha. In some embodiments, the isoproturon or salt thereof is applied at a rate of approximately 375 g ai / ha to approximately 1,500 g ai / ha and the compound of formula (I) of salt or ester thereof is applied at a rate of approximately 2.5 g ae / ha to approximately 10 g ae / ha. In certain modalities, the methods use the compound of the formula (I) or its benzyl or n-butyl ester and isoproturon or salt thereof for the control of AMARE, SINAR, GALAP, LAMPU or VERPE.
In certain embodiments of the compositions and methods described in this application, the compound of formula (I) or salt or ester thereof is used in combination with linuron or salt thereof. As for the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to linuron or salt thereof is within the range of approximately 1: 2250 to approximately 6: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to linuron or salt thereof is within the range of approximately 1:39 to approximately 1:19. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to linuron or salt thereof is within the range of approximately 1: 1364 to approximately 1: 1. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and linuron or salt thereof. With respect to the methods, in certain modalities, the methods comprise contact of undesirable vegetation or locus thereof or application to the soil or water of a composition described in this application to prevent the appearance or growth of vegetation. In some embodiments, the composition is applied at an application rate of approximately 52 grams per hectare (g ai / ha) to approximately 4,800 g ai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of the active ingredient of approximately 53 grams per hectare (g ai / ha) to approximately 3,050 g ai / ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contact of undesirable vegetation or locus thereof or application to soil or water to prevent the appearance or growth of vegetation with a compound of formula (I) or salt or ester thereof and linuron or salt thereof , for example, sequentially or simultaneously. In some embodiments, linuron or salt thereof is applied at a rate of approximately 50 g ai / ha to approximately 4,500 g ai / ha and the compound of formula (I) of salt or ester thereof is applied at a rate of approximately 2 g ae / ha to approximately 300 g ae / ha. In some embodiments, linuron or salt thereof is applied at a rate of approximately 50 g ai / ha to approximately 620 g ai / ha and the compound of formula (I) of salt or ester thereof is applied at a rate of approximately 16 g ae / ha to approximately 32 g ae / ha. In certain embodiments, the methods use the compound of the formula (I) or its benzyl or n-butyl ester and linuron or salt thereof for the control of BRAPP.
In certain embodiments of the compositions and methods described in this application, the compound of formula (I) or salt or ester thereof is used in combination with metibenzuron or salt thereof. As for the compositions, in some embodiments, the weight ratio of the compound of the formula (I) or salt or ester thereof to metibenzuron or salt thereof is within the range of approximately 1: 1400 to approximately 4: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to metibenzuron or salt thereof is within the range of approximately 1: 909 to approximately 1: 1. In certain embodiments, the compositions comprise the compound of the formula (I) or its benzyl or n-butyl ester and metibenzuron or salt thereof. With respect to the methods, in certain modalities, the methods comprise contact of undesirable vegetation or locus thereof or application to the soil or water of a composition described in this application to prevent the appearance or growth of vegetation. In some embodiments, the composition is applied at an application rate of the active ingredient of approximately 72 grams per hectare (g ai / ha) to approximately 3,100 g ai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of the active ingredient of approximately 73 grams per hectare (g ai / ha) to approximately 2,050 g ai / ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contact of undesirable vegetation or locus thereof or application to soil or water to prevent the appearance or growth of vegetation with a compound of formula (I) or salt or ester thereof and metibenzuron or salt thereof , for example, sequentially or simultaneously. In some embodiments, metibenzuron or its salt is applied at a rate of approximately 70 g ai / ha to approximately 2,800 g ai / ha and the compound of formula (I) of salt or ester thereof is applied at a rate of approximately 2 g ae / ha to approximately 300 g ae / ha. In certain embodiments, the methods use the compound of formula (I) or its benzyl or n-butyl ester and metibenzuron or salt thereof.
In certain embodiments of the compositions and methods described in this application, the compound of formula (I) or salt or ester thereof is used in combination with metribuzin or salt thereof. As for the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to metribuzin or salt thereof is within the range of approximately 1: 2800 to approximately 6: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to metribuzin or salt thereof is within the range of approximately 1: 509 to approximately 1: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to metribuzin or salt thereof is within the range of approximately 1: 168 to approximately 1: 1. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and metribuzin or salt thereof. With respect to the methods, in certain modalities, the methods comprise contact of undesirable vegetation or locus thereof or application to the soil or water of a composition described in this application to prevent the appearance or growth of vegetation. In some embodiments, the composition is applied at an application rate of approximately 52 grams per hectare (g ai / ha) to approximately 5,900 g ai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of the active ingredient of approximately 55 grams per hectare (g ai / ha) to approximately 2,300 g ai / ha based on the total amount of active ingredients in the composition. In some modalities, the methods include contact of undesirable vegetation or locus thereof or application to soil or water to prevent the appearance or growth of vegetation with a compound of formula (I) or salt or ester thereof and metribuzin or salt thereof , for example, sequentially or simultaneously. In some embodiments, metribuzin or salt thereof is applied at a rate of approximately 50 g ai / ha to approximately 5,600 g ai / ha and the compound of formula (I) of salt or ester thereof is applied at a rate of approximately 2 g ae / ha to approximately 300 g ae / ha. In some embodiments, metribuzin or salt thereof is applied at a rate of approximately 25 g ai / ha to approximately 420 g ai / ha and the compound of formula (I) of salt or ester thereof is applied at a rate of approximately 2 , 5 g ae / ha to approximately 32 g ae / ha. In certain modalities, the methods use the compound of the formula (I) or its benzyl or n-butyl ester and metribuzin or its salt for the control of SETFA, KCHSC, LAMPU, SASKR, CHEAL or SINAR.
In certain embodiments of the compositions and methods described in this application, the compound of formula (I) or salt or ester thereof is used in combination with propanyl or salt thereof. As for the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to propanyl or salt thereof is within the range of approximately 1: 2800 to approximately 1: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to propanyl or salt thereof is within the range of approximately 1: 767 to approximately 1:12. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to propanyl or salt thereof is within the range of approximately 1: 772 to approximately 1:12. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to propanyl or salt thereof is within the range of approximately 1: 384 to approximately 1:24. In certain embodiments, the compositions provided in this application comprise the compound of formula (I) or its benzyl or n-butyl and propanyl ester. In one embodiment, the composition comprises the compound of the formula (I) and propanyl, wherein the weight ratio of the compound of the formula (I) to propanyl is approximately 1: 384 to approximately 1:48. In one embodiment, the composition comprises the compound of the formula (I) and propanyl, wherein the weight ratio of the compound of the formula (I) to propanyl is approximately 1: 384 to approximately 1:48. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and propanyl, wherein the weight ratio of the benzyl ester of the compound of formula (I) to propanyl is approximately 1: 767 to approximately 1:24 . In one embodiment, the composition comprises the n-butyl ester of the compound of formula (I) and propanyl, wherein the weight ratio of the n-butyl ester of the compound of formula (I) to propanyl is approximately 1: 210.
With respect to the methods, in certain modalities, the methods comprise contact of undesirable vegetation or locus thereof or application to the soil or water of a composition described in this application to prevent the appearance or growth of vegetation. In some embodiments, the composition is applied at an active ingredient application rate of approximately 422 grams per hectare (g ai / ha) to approximately 5,900 g ai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of approximately 425 grams per hectare (g ai / ha) to approximately 3,400 g ai / ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contact of undesirable vegetation or locus thereof or application to soil or water to prevent the appearance or growth of vegetation with a compound of formula (I) or salt or ester thereof and propane or salt of it, for example, sequentially or simultaneously. In some embodiments, propanyl or salt thereof is applied at a rate of approximately 420 g ai / ha to approximately 5,600 g ai / ha and the compound of formula (I) of salt or ester thereof is applied at a rate of approximately 2 g ae / ha to approximately 300 g ae / ha. In some embodiments, propanyl or salt thereof is applied at a rate of approximately 210 g ai / ha to approximately 6,720 g ai / ha and the compound of formula (I) of salt or ester thereof is applied at a rate of approximately 2 g equivalent of acid per hectare (g ae / ha) at approximately 70 g ae / ha. In some embodiments, propanyl or salt thereof is applied at a rate of approximately 420 g ai / ha to approximately 3,360 g ai / ha and the compound of formula (I) of salt or ester thereof is applied at a rate from approximately 4 g equivalents of acid per hectare (g ae / ha) to approximately 35 g ae / ha. In some embodiments, propanyl or salt thereof is applied at a rate of approximately 420 g ai / ha to approximately 3,360 g ai / ha and the compound of formula (I) of salt or ester thereof is applied at a rate of approximately 4.38 g equivalent of acid per hectare (g ae / ha) to approximately 35 g a- e / ha. In certain embodiments, the methods use the compound of formula (I), or its benzyl ester or n-butyl and propanyl. In one embodiment, the methods use the compound of the formula (I) and propanyl, where the compound of the formula (I) is applied at a rate of approximately 4.38 g equivalent of acid per hectare (g ae / ha) to approximately 35 g ae / ha, and propanil is applied at a rate of approximately 420 g ai / ha to approximately 3,360 g ai / ha. In one embodiment, the methods use the benzyl ester of the compound of formula (I) and propanyl, in which the benzyl ester of the compound of formula (I) is applied at a rate of approximately 4.38 g equivalents of acid per hectare (g ae / ha) to approximately 35 g ae / ha, and propanyl is applied at a rate of approximately 420 g ai / ha to approximately 3,360 g ai / ha. In one embodiment, the methods use the n-butyl ester of the compound of formula (I) and propanyl, in which the n-butyl ester of the compound of formula (I) is applied at a rate of approximately 16 g equivalents of acid per hectare (g ae / ha), and propanil is applied at a rate of approximately 3,360 g ai / ha. In certain embodiments, the methods and compositions using the compound of formula (I) or salt 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 in this application, the compound of formula (I) or salt or ester thereof is used in combination with pyridate. As for the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to pyridate is within the range of approximately 1: 800 to approximately 12: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to pyridate is within the range of approximately 1: 545 to approximately 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 modalities, the methods comprise contact of undesirable vegetation or locus thereof or application to the soil or water of a composition described in this application to prevent the appearance or growth of vegetation. In some embodiments, the composition is applied at an application rate of the active ingredient of approximately 27 grams per hectare (g ai / ha) to approximately 1,800 g ai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of the active ingredient of approximately 28 grams per hectare (g ai / ha) to approximately 1,350 g ai / ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contact of undesirable vegetation or locus thereof or application to soil or water to prevent the appearance or growth of vegetation with a compound of formula (I) or salt or ester thereof and pyridate, for example, sequentially or simultaneously. In some embodiments, pyridate is applied at a rate of a-approximately 25 g ai / ha to approximately 1,600 g ai / ha and the compound of formula (I) of salt or ester thereof is applied at a rate of approximately 2 g ae / ha to approximately 300 g ae / ha. In certain embodiments, the methods use the compound of formula (I) or its benzyl or n-butyl ester and pyridate.
In certain embodiments of the compositions and methods described in this application, the compound of formula (I) or salt or ester thereof is used in combination with siduron or salt thereof. As for the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to siduron or salt thereof is within the range of approximately 1: 4500 to approximately 2: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to siduron or salt thereof is within the range of approximately 1: 2728 to approximately 1: 3. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and siduron or salt thereof. With respect to the methods, in certain modalities, the methods comprise contact of undesirable vegetation or locus thereof or application to the soil or water of a composition described in this application to prevent the appearance or growth of vegetation. In some embodiments, the composition is applied at an application rate of the active ingredient of approximately 142 grams per hectare (g ai / ha) to approximately 9,300 g ai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of the active ingredient of approximately 143 grams per hectare (g ai / ha) to approximately 6,050 g ai / ha based on the total amount of active ingredients in the composition. In some modalities, the methods comprise contact of undesirable vegetation or locus thereof or application to soil or water to prevent the appearance or growth of vegetation with a compound of formula (I) or salt or ester thereof and siduron or salt thereof , for example, sequentially or simultaneously. In some embodiments, siduron or salt thereof is applied at a rate of approximately 140 g ai / ha to approximately 9,000 g ai / ha and the compound of formula (I) of salt or ester thereof is applied at a rate of approximately 2 g ae / ha to approximately 300 g ae / ha. In certain embodiments, the methods use the compound of formula (I) or its benzyl or n-butyl ester and siduron or salt thereof.
In certain embodiments of the compositions and methods described in this application, the compound of formula (I) or salt or ester thereof is used in combination with simazine or salt thereof. As for the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to simazine or salt thereof is within the range of approximately 1: 4250 to approximately 2: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to simazine or salt thereof is within the range of approximately 1: 2728 to approximately 1: 3. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to simazine or salt thereof is within the range of approximately 1: 280 to approximately 1: 17.5. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and simazine or salt thereof. With respect to the methods, in certain modalities, the methods comprise contact of undesirable vegetation or locus thereof or application to the soil or water of a composition described in this application to prevent the appearance or growth of vegetation. In some embodiments, the composition is applied at an application rate of approximately 142 grams per hectare (g ai / ha) to approximately 8,800 g ai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of the active ingredient of approximately 143 grams per hectare (g ai / ha) to approximately 6,050 g ai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of approximately 568 grams per hectare (g ai / ha) to approximately 2,272 g ai / ha based on the total amount of active ingredients in the composition. In some modalities, the methods comprise contact of undesirable vegetation or locus thereof or application to soil or water to prevent the appearance or growth of vegetation with a compound of formula (I) or salt or ester thereof and simazine or salt thereof , for example, sequentially or simultaneously. In some embodiments, simazine or salt thereof is applied at a rate of approximately 140 g ai / ha to approximately 8,500 g ai / ha and the compound of formula (I) of salt or ester thereof is applied at a rate of approximately 2 g ae / ha to approximately 300 g ae / ha. In some embodiments, simazine or salt thereof is applied at a rate of approximately 560 g ai / ha to approximately 2,240 g ai / ha and the compound of formula (I) of salt or ester thereof is applied at a rate of approximately 8 g ae / ha to approximately 32 g ae / ha. In certain modalities, the methods use the compound of the formula (I) or its benzyl or n-butyl ester and simazine or salt thereof for the control of BRAPP, ECHCG, ECHCO, CYPIR or XANST.
In certain embodiments of the compositions and methods described in this application, the compound of formula (I) or salt or ester thereof is used in combination with symmetrine or salt thereof. As for the compositions, in some embodiments, the weight ratio of the compound of formula (I) or its salt or ester to symmetrine or its salt is within the range of approximately 1: 1000 to approximately 12: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to symmetry or salt thereof is within the range of approximately 1: 682 to approximately 6: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to symmetry or salt thereof is within the range of approximately 1:56 to approximately 1: 3.5. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and symmetrine or salt thereof. With respect to the methods, in certain modalities, the methods comprise contact of undesirable vegetation or locus thereof or application to the soil or water of a composition described in this application to prevent the appearance or growth of vegetation. In some embodiments, the composition is applied at an application rate of approximately 27 grams per hectare (g ai / ha) to approximately 2,300 g ai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of the active ingredient of approximately 28 grams per hectare (g ai / ha) to approximately 1,650 g ai / ha based on the total amount of active ingredients in the composition. In some modalities, the methods comprise contact of undesirable vegetation or locus thereof or application to soil or water to prevent the appearance or growth of vegetation with a compound of formula (I) or salt or ester thereof and symmetry or salt thereof , for example, sequentially or simultaneously. In some embodiments, symmetrine or salt thereof is applied at a rate of approximately 25 g ai / ha to approximately 2,000 g ai / ha and the compound of formula (I) of salt or ester thereof is applied at a rate of approximately 2 g ae / ha to approximately 300 g ae / ha. In some embodiments, symmetrine or salt thereof is applied at a rate of approximately 110 g ai / ha to approximately 450 g ai / ha and the compound of formula (I) of salt or ester thereof is applied at a rate of approximately 8 g ae / ha to approximately 32 g ae / ha. In certain modalities, the methods use the compound of the formula (I) or its benzyl or n-butyl ester and symmetry or salt thereof for the control of ECHCO, ECHOR, CYPIR, CYPRO, FIMMI or LEFCH.
In certain embodiments of the compositions and methods described in this application, the compound of formula (I) or salt or ester thereof is used in combination with tebutiuron or salt thereof. As for the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to tebutiuron or salt thereof is within the range of approximately 1: 2240 to approximately 2: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to tebutiuron or salt thereof is within the range of approximately 1: 1818 to approximately 1: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to tebutiuron or salt thereof is within the range of approximately 1: 420 to approximately 1: 6.5. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and tebutiuron or salt thereof. With respect to the methods, in certain modalities, the methods comprise contact of undesirable vegetation or locus thereof or application to the soil or water of a composition described in this application to prevent the appearance or growth of vegetation. In some embodiments, the composition is applied at an application rate of the active ingredient of approximately 142 grams per hectare (g ai / ha) to approximately 4,780 g ai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an active ingredient application rate of approximately 143 grams per hectare (g ai / ha) to approximately 4,100 g ai / ha based on the total amount of active ingredients in the composition. In some modalities, the methods comprise contact of undesirable vegetation or locus thereof or application to soil or water to prevent the appearance or growth of vegetation with a compound of formula (I) or salt or ester thereof and tebutiuron or salt thereof , for example, sequentially or simultaneously. In some embodiments, tebutiuron or salt thereof is applied at a rate of approximately 140 g ai / ha to approximately 4,480 g ai / ha and the compound of formula (I) of salt or ester thereof is applied at a rate of approximately 2 g ae / ha to approximately 300 g ae / ha. In some embodiments, tebutiuron or salt thereof is applied at a rate of approximately 140 g ai / ha to approximately 3,360 g ai / ha and the compound of formula (I) of salt or ester thereof is applied at a rate of approximately 4 g ae / ha to approximately 32 g ae / ha. In certain modalities, the methods use the compound of the formula (I) or its benzyl or n-butyl ester and tebutiuron or salt thereof to control BRSNN, CIRAR, CYPES, ECHCG, IPOHE or XANST.
In certain embodiments of the compositions and methods described in this application, the compound of formula (I) or salt or ester thereof is used in combination with terbuthylazine or salt thereof. As for the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to terbuthylazine or salt thereof is within the range of approximately 1: 1500 to approximately 3: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to terbuthylazine or salt thereof is within the range of approximately 1: 1018 to approximately 1: 2.5. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to terbuthylazine or salt thereof is within the range of approximately 1:62 to approximately 1:31. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and terbuthylazine or salt thereof. With respect to the methods, in certain modalities, the methods comprise contact of undesirable vegetation or locus thereof or application to the soil or water of a composition described in this application to prevent the appearance or growth of vegetation. In some embodiments, the composition is applied at an application rate of the active ingredient of approximately 127 grams per hectare (g ai / ha) to approximately 3,300 g ai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of the active ingredient of approximately 128 grams per hectare (g ai / ha) to approximately 2,290 g ai / ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contact of undesirable vegetation or locus thereof or application to soil or water to prevent the appearance or growth of vegetation with a compound of formula (I) or salt or ester thereof and terbuthylazine or salt thereof , for example, sequentially or simultaneously. In some embodiments, terbuthylazine or salt thereof is applied at a rate of approximately 125 g ai / ha to approximately 3,000 g ai / ha and the compound of formula (I) of salt or ester thereof is applied at a rate of approximately 2 g ae / ha to approximately 300 g ae / ha. In some embodiments, terbuthylazine or salt thereof is applied at a rate of approximately 125 g ai / ha to approximately 1,000 g ai / ha and the compound of formula (I) of salt or ester thereof is applied at a rate of approximately 16 g ae / ha to approximately 32 g ae / ha. In certain embodiments, the methods use the compound of formula (I) or its benzyl or n-butyl ester and terbuthylazine or salt thereof for the control of XANST.
The components of the mixtures described in this application can be applied separately or as part of a multipart herbicide system.
The mixtures described in this application can be applied in conjunction with one or more herbicides to control a wider variety of undesirable vegetation. When used in conjunction with other herbicides, the composition can be formulated with another herbicide or herbicides, mixing tank with another herbicide or herbicides or applied sequentially with another herbicide or herbicides. Some herbicides that can be used in conjunction with the compositions and methods described in this application include, but are not limited to: 4-CPA; 4-CPB; 4-CPP; 2,4-D; 2,4-D choline salt, 2,4-D, 2,4-DB esters and amines; 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, acloni-fen, acrolein, alachlor, allidochlor, alloxidim, allyl alcohol, alorac, ametridione, amethrine, amibuzin, amicarbazone, amidosulfuron, aminocyclopyrachlor, ami-nopiralid, amiprofos-methyl, amitrol, amitrol, amitrol, sulfamide , asulam, atraton, azafenidin, azimsulfuron, aziprotrine, barban, BCPC, be-flubutamide, benazoline, bencarbazone, benfluralin, benfuresate, bensulfu-ron-methyl, bensulide, bentiocarb, benzadox, benzfen, benzofen, benzpram , benzoylprop, benztiazuron, bialafos, bicyclopyrone, bifenox, bilanafos, bispiribac-sodium, borax, bromacil, bromobonyl, bromobutide, bromophenoxim, brompirazon, butachlor, butafenacil, butamidon, butanidone, butenachlor, butenachlor, butenachlor , cacodylic acid, cafenstrol, calcium chlorate, calcium cyanamide, cambendichlor, carbasulam, carbetamide, carboxazole chlorprocarb, carfentrazone-ethyl, CDEA, CEPC, clomethoxyfen, chloramben, clo ranocril, clorazifop, chlorazin, chlorinuron, chlorinate, chloreturon, chlorfenac, chlorfenprop, chlorflurazole, chlorflurenol, chloridazon, chlorimuron, chlorornitrophen, chloropon, chloroxuron, chloroxynil, chlorpro-fam, clorsulfuron, chloride, chlortil, chloride cinosulfuron, cisanilide, cletodim, cliodinate, clodinafop-propargil, clofop, clomazone, clo-meprop, cloprop, cloproxidim, clopyralid, chloransulam-methyl, CMA, copper sulphate, CPMF, CPPC, credazine, cresol, cumiluron, cyclol, cumiluron to, cycloate, cyclosulfamuron, cycloxidim, cycluron, cihalofop-butyl, cyiperquat, cyprazine, cyprazole, cipromid, daimuron, dalapon, dazomet, delaclor, desme-difam, demetrine, di-alate, dicamba, dichlorohydrate, dichloride, dichloride, dichloride, dichloride, dichloride, dichloride, dichloride dichlorprop-P, diclofop-methyl, diclosulam, dietamquat, dietathyl, dife-nopentene, diphenoxuron, difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimetachlor, dimetamethrin, dimetenamid, dimetenamid-di, dimetenamid-di, dimetenamid-P, dimetenamid-di nitramine, dinofenate, dinoprop, dinosam, dinoseb, dinoterb, diphenamid, dipropetrin, diquat, disul, dithiopir, DMPA, DNOC, DS-MA, EBEP, eglinazine, endotal, epronaz, EPTC, erbon, esprocarb, etalflurali-na, etbenzam etametsulfuron, etidimuron, etiolate, etobenzamid, etoben-zamid, etofumesate, ethoxyfen, ethoxysulfuron, ethinofen, etnipromid, etobenza-nid, EXD, fenasulam, feneno, fenoxaprop, phenoxaprop-P-ethyl-isoxy-propyl, phenoxaprop fenoxasulfone, fenteracol, fentiaprop, fentrazamide, fe-nuron, ferrous sulfate, flamprop, flamprop-M, flazasulfuron, florasulam, fluazi-fop, fluazifop-P-butyl, fluazolate, flucarbazone, flucetosulfuron, flucloren, fluorine, fluorine -ethyl, flumetsulam, flumezin, flumiclorac-pentil, flumioxazin, flumipropin, fluometuron, fluorodifen, fluoroglycofen, fluoromidine, fluoronitrofen, fluotiuron, flupoxam, flupropacil, flupropanate, flupirsuroxon, flupirsuroxon, flupirsulfuron, flutiacet fomesafen, foramsulfuron, fosamina, fumiclorac, furiloxifen, glufosinate, ammonium glu-phosinate, glufosinate-P-ammonium, glyphosate, halauxifene, halauxife-no-methyl, halosafen, halosulfuron-methyl, haloxidine, haloxidine, haloxifin P-methyl, hexachloroacetone, hexaflurate, imazametabenz, imazamox, ima-zapic, imazapyr, imazaquin, imazosulfuron, imazetapyr, indanofan, indaziflam, iodobonyl, iodomethane, iodosulfuron, iodosulfuron, iodine sulfate isocil, isometiozin, isonoru-ron, isopolinate, isopropalin, isouron, isoxaben, isoxaclortol, isoxaflutol, iso-xapirifop, carbutilate, cetospiradox, lactophen, lenacil, esters and amines of MAA, MMA, MCAP, MCMA, MCPA, MCPA, MCAP, MCPA, MCAP, MCPA, MCPA, MCAP, MCPA, MCAP, MCPA mecoprop-P, medino-terb, mefenacet, mefluidide, mesoprazine, mesosulfuron, mesotrione, metam, metamifop, metamitron, metazachlor, metazosulfuron, metflurazon, me-tabenztiazuron, metalpropalin, metazol, metiobencon, metiobenconb, metiobencarb, metiobencarb, metiobencarb, metiobencarb oprotrin, methyl bromide, methyl isothiocyanate, methyl-dimron, metobenzuron, metobromuron, metolachlor, metosulam, methoxyuron, metsulfuron, metsulfuron-methyl, molinate, monalide, monisouron, mo-nocloroacetic acid, monolinuronide, monolinuron, monolinuron, monolinuron, monolinuron, , napropamide, naptalam, neburon, nicosulfuron, nipyraclofen, nitralin, nitro-hay, nitrofluorfen, norflurazon, noruron, OCH, orbencarb, ortho-dichlorobenzene, ortosulfamuron, orizalin, oxadiargil, oxiruroxy, oxirazuronoxoxazone , parafluron, para-quat, pebulate, pelargonic acid, pendimethalin, penoxsulam, pentachlorophenol, pentanochlor, pentoxazone, perfluidone, petoxamid, phenisofam, fenmedi-fam, fenmedifam-ethyl, phenobenzuron, phenylphenyl acetate, pylamine PEGxaden, piperophos, potassium arsenite, potassium azide, potassium cyanide, pretilachlor, primisulfuron-methyl, prociazine, prodiamine, proflu-azole, profluralin, profoxidine, progli nazine, prohexadione-calcium, prometon, promethrin, pronamide, propachlor, propaquizafop, propazine, profam, propi-soclor, propoxycarbazone, propyrisulfuron, propizamide, prosulfaline, prosul-focarb, prosulfuron, proxan, prinaclor, pidanon, pidanon, pyranon, piraclon pyrazulfotol, pyrazogyl, pyrazolinate, pirazosulfuron-ethyl, pyrazoxifen, piribenzoxim, piributicarb, piriclor, pyridafol, piriftalid, piriminobac, pirimisulfan, piritiobac-sodium, pyroxasulfone, piroxsulam, quinclorac, quinofac, quinmeric, quinofac P-ethyl, rodetanil, rimsulfuron, saflufenacil, S-metolachlor, sebutilazine, secbumeton, setoxidim, simeton, SMA, sodium arsenite, sodium azide, sodium chlorate, sulcotrione, sulfalate, sulfentrazone, sulfometuron, sulfosate, sulfosulfuron, sulfosulfuron , sulglicapin, swep, SIN-523, TCA, tebutam, tefuriltrione, tembotrione, tepraloxidim, terbacil, terbu-carb, terbuclor, terbumeton, terbutrin, tetrafluron, tenilclor, tiazafluron, tiazo-p ir, tidiazimin, tidiazuron, tiencarbazone-methyl, tifensulfuron, tifensulfurn-methyl, thiobencarb, tiocarbazil, thioclorin, topramezone, tralcoxidim, triafamone, tri-alate, triasulfuron, triaziflamine, tribur, triaziflamine, triben, triaziflamine and salts of triclopyr, tridifan, trietazine, trifloxisulfuron, trifluralin, triflusulfuron, trifop, trifopsima, trihydroxytriazine, trimeturon, tripro-pindan, tritac tritosulfuron, vernolate, xylachlor and the same isomers, and isomers, and esters.
The compositions and methods described in this application, can also be used together with glyphosate, 5-enolpyruvylshikimato-3-phosphate synthase (EPSP) inhibitors, glufosinate, glutamine syntetase inhibitors, dicamba, phenoxy auxins, pyridyloxy auxins, synthetic auxins, auxin transport inhibitors, aryloxyphenoxypropionates, cyclohexanediones, phenylpyrazolines, acetyl CoA carboxylase inhibitors (ACCa se), imidazolinones, sulfonylureas, pyrimidinylthiobenzoates, triazolopyrimidines (acetonyl acid) sulfonyl oxides AHAS), 4-hydroxyphenyl-pyruvate dioxigenase (HPPD) inhibitors, phytene desaturase inhibitors, carotenoid biosynthesis inhibitors, protoporphyrinogen oxidase (PPO) inhibitors, cellulose biosynthesis inhibitors, mitosis inhibitors, microtubu- inhibitors them, very long chain fatty acid inhibitors, fatty acid biosynthesis inhibitors lipid, photosystem I inhibitors, photosystem II inhibitors, triazines, and bromoxynil in cultures tolerant to glyphosate, tolerant to EPSP synthase inhibitor, tolerant to glufosinate, tolerant to glutamine synthetase inhibitor, tolerant to dicamba, tolerant phenoxy auxin, tolerant to pyridyloxy auxin, tolerant to auxin, tolerant to auxin transport inhibitor, tolerant to aryloxyphenoxypropionate, tolerant to cyclohexanedione, tolerant to phenylpyrazoline, tolerant to ACCase, tolerant to imidazolinone, tolerant to sulfonylurea, tolerant to sulfonylurea to pyrimidinylthiobenzoate, tolerant to triazolopyrimidine, tolerant to sulfonylaminocarbonyltriazolinone, tolerant to ALS or AHAS, tolerant to HPPD, tolerant to the phyto-ene desaturase inhibitor, tolerant to the carotenoid biosynthesis inhibitor, tolerant to cellulose inhibitors, tolerant to cellulose inhibitors tolerant to mitosis inhibitor, tolerant to microt inhibitor ubulae, tolerant to very long chain fatty acid inhibitor, tolerant to lipid and fatty acid biosynthesis inhibitor, tolerant to photosystem I inhibitor, tolerant to photosystem II inhibitor, tolerant to triazine and tolerant to bromo-xinil and cultures that they have multiple or stacked lines giving tolerance to multiple chemicals and / or multiple modes of action through single and / or multiple resistance mechanisms. In some embodiments, the compound of formula (I) or salt or ester thereof and complementary herbicide or salt or ester thereof is used in combination with herbicides that are selective for the crop being treated and that complete the spectrum of controlled weeds by these compounds at the application rate employed. In some embodiments, the compositions described in this application and other complementary herbicides are applied at the same time, as a combination formulation, as a tank mix, or as a sequential application.
In some embodiments, the compositions described in this application are used in combination with one or more herbicide phytoprotectors, such as AD 67 (MON 4660), benoxacor, bentiocarb, brassinolide, cloquintocet (mexil), ciometrinil, daimuron, diclormid, diciclonon, dimepipera- to, disulfoton, fenclorazol-ethyl, fenclorim, flurazol, fluxofenim, furilazol, proteins harpina, isoxadifen-ethyl, jiecaowan, jiecaoxi, mefenpir-diethyl, mefenato, naphthalic anhydride (NA), oxabetrinyl acid, R29148 and am298 -sulfonylbenzoic, to increase its selectivity. In some modalities, phytoprotectors are used in rice, cereal, corn or more environments. In some embodiments, the phytoprotectant is cloquintocet or an ester or salt thereof. In certain embodiments, cloquintocet is used to antagonize the dangerous effects of compositions on rice and cereals. In some embodiments, the phytoprotector is cloquintocet (mexil).
In some embodiments, the compositions described in this application are used in combination with one or more plant growth regulators, such as 2,3,5-triiodiodobenzoic acid, IAA, IBA, naphthalene-tamide, α-naphthalenoacetic acids, benzyladenine, alcohol 4-hydroxyphenethyl, kinetin, zeatin, endothal, etefon, pentachlorophenol, tidiazuron, tribufos, avi-glycine, gibberellins, gibberellic acid, abscisic acid, ancimidol, phosamine, glyphosine, isopyrimol, jasonic acid, mezatide, mezatide, hydrazide , 5-triiodobenzoic acid, morphactins, dichlorflurenol, flurprimidol, mefluidide, paclobutrazol, tetciclacis, uniconazole, brassinolide, brassinolide-ethyl, cycloheximide, ethylene, metasulfocarb, prohexadione, triapentenol and triapentenol.
In some modalities, plant growth regulators are used in one or more crops or environments, such as rice, cereal crops, corn, plus, broadleaf crops, rapeseed / canola, lawn, pineapple, sugar cane, sunflower, pasture , pastures, natural pastures, fallow, lawn, tree and vine orchards, plantation crops, vegetables and non-culture (ornamental) environments. 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 beneficial effect on plants.
In some embodiments, the compositions provided in this application further comprise at least one agriculturally acceptable adjuvant or vehicle. Suitable adjuvants or vehicles should not be phytotoxic to valuable crops, particularly at the concentrations employed in applying selective weed control compositions in the presence of crops, and should not react chemically with herbicide components or other ingredients in the composition. Such mixtures can be designed for application directly to weeds or their locus or they can be concentrated or formulations that are usually diluted with additional vehicles and adjuvants before application. They can be solids, such as, for example, powders, granules, water-dispersible granules, or humidifiable powders or liquids, such as, for example, emulsifiable concentrates, solutions, emulsions or suspensions. They can also be supplied as a cake mix or mixing tank.
Suitable agricultural vehicles and adjuvants include, but are not limited to, concentrated crop oil; nonylphenol ethoxylate; benzylcocoalkylldimethyl quaternary ammonium salt; mixture of petroleum hydrocarbon, alkyl esters, organic acid and anionic surfactant; Cg-Cn al-kilpoliglycoside; phosphate alcohol ethoxylate; natural primary alcohol ethoxylate (C12-C16); Di-sec-butylphenol block copolymer EO-PO; polysiloxane-methyl termination; nonylphenol ethoxylate + urea ammonium nitrate; emulsified methylated seed oil; tridecyl ethoxylate (synthetic) alcohol (8EO); tallow amine ethoxylate (15 EO); PEG (400) dioleate-99.
Liquid vehicles that can be used include water and organic solvents. Organic solvents include, but are not limited to, petroleum or hydrocarbon fractions such as mineral oil, aromatic solvents, paraffinic oils, and the like; vegetable oils such as soybean oil, rapeseed oil, olive oil, castor oil, sunflower oil, coconut oil, corn oil, cotton oil, linseed oil, palm oil, peanut oil, safflower oil , sesame oil, tung oil and the like; esters of the above vegetable oils; esters of mono or dihydrated, trihydrated, or other minor polyalcohols (containing 4-6 hydroxy), such as 2-ethylhexyl stearate, n-butyl oleate, isopropyl myristate, propylene glycol dioleate, succinate di-octyl, di-butyl adipate, di-octyl phthalate and the like; esters of mono-, di- and polycarboxylic acids and the like. Specific organic solvents include, but are not limited to, toluene, xylene, petroleum naphtha, crop oil, acetone, ethyl methyl ketone, cyclohexanone, trichlorethylene, perchlorethylene, ethyl acetate, amyl acetate, butyl acetate, monomethyl propylene glycol ether and monomethyl diethylene glycol ether, methyl alcohol, ethyl alcohol, isopropyl alcohol, amyl alcohol, ethylene glycol, propylene glycol, glycerin, / / - methyl-2-pyrrolidinone, A /, A / -dimethyl alkylamides , dimethyl sulfoxide, liquid fertilizers and the like. In certain embodiments, water is the vehicle for diluting concentrates.
Suitable solid vehicles include but are not limited to talc, pyrophyllite clay, silica, attapulgus clay, kaolin clay, diatomite, chalk, diatomaceous earth, mistletoe, calcium carbonate, bentonite clay, Fuller earth, cottonseed husks, cotton flour, flour wheat, soy flour, pumice, wood flour, nutshell flour, lignin, cellulose and the like.
In some embodiments, the compositions described in this application still comprise one or more surface-active agents. In some embodiments, such active surface agents are employed in both solid and liquid compositions, and in certain embodiments, designed to be diluted with the vehicle before application. Surface active agents can be anionic, cationic or non-ionic in character and can be used as emulsifying agents, humidifying agents, suspending agents, or for other purposes. Surfactants that can also be used in the present formulations are described, inter alia, in "McCutcheon's Detergents 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, alkyl sulfate salts, such as diethanolammonium lauryl sulfate; alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products, such as nonylphenol-Cis ethoxylate; alcohol alkylene oxide addition products, such as C1-6 alcohol tridecyl ethoxylate; soaps, such as sodium stearate; 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; quaternary amines, such as trimethylammonium lauryl chloride; polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; salts of mono- and dialkyl phosphate esters; vegetable or seed oils such as soybean oil, rapeseed / canola oil, olive oil, castor oil, sunflower oil, coconut oil, corn oil, cotton oil, linseed oil, olive oil palm oil, peanut oil, safflower oil, sesame oil, tung oil and the like; and esters of the above vegetable oils, and in certain embodiments, methyl esters.
In some embodiments, these materials, such as vegetable or seed oils and their esters, can be used interchangeably as an agricultural adjuvant, as a liquid carrier or as a surface active agent.
Other exemplary additives for use in the compositions provided in this application include but are not limited to compatibilizing agents, anti-foaming agents, sequestering agents, neutralizing agents and buffers, corrosion inhibitors, dyes, flavorings, dispersing agents, penetration aids, adhesion, dispersing agents, thickening agents, freezing point depressants, antimicrobial agents, and the like. The compositions can also contain other compatible components, for example, other herbicides, plant growth regulators, fungicides, insecticides, and the like and can be formulated with liquid or solid fertilizers, particulate fertilizer vehicles such as ammonium nitrate, urea and the like.
In some embodiments, the concentration of the active ingredients in the compositions described in this application is from 0.0005 to 98 weight percent. In some embodiments, the concentration is 0.0006 to 90 weight percent. In compositions designed to be employed as concentrates, the active ingredients, in certain embodiments, are present in a concentration of 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 application. The diluted compositions normally applied to weeds or the weed locus contain, in certain embodiments, 0.0052 to 25.0 weight percent of active ingredient and in certain modalities contain 0.01 to 15 weight percent of ingredient active.
The present compositions can be applied to weeds or their locus by the use of conventional particulate or air sprayers, sprayers and granule applicators, by the addition to irrigation or rice paddy water, and by other conventional means known to those skilled in the art. in the technique.
The modalities described and the 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 in this application will be evident to a person of ordinary skill in the technique without departing from the spirit and scope of the claimed subject matter.
Examples Results in Examples I, II, III, IV, and V are greenhouse test results. Example I. Evaluation of Herbicidal Mixtures Applied to Post-emergence Foliar for Weed Control in Direct Seeded Rice The seeds or nuts of the desired test plant species were planted in a soil matrix prepared by mixing a loam or sandy loam soil {by example, 28.6 percent sludge, 18.8 percent clay and 52.6 percent sand, with a pH of approximately 5.8 and an organic matter content of approximately 1.8 percent) and a- limestone sand in an 80 to 20 ratio. The soil matrix was contained in plastic pots with a volume of 1 quarter and a surface area of 83.6 square centimeters (cm2). When required to ensure good germination and healthy plants, a fungicide treatment and / or other chemical or physical treatment was applied. The plants were grown for 8 to 22 days in a greenhouse with a photoperiod of approximately 14 h that was maintained at approximately 29Ό during the day and 26 * 0 during the night. The nutrients (Peters Excel® 15-5-15 5-Ca 2 mg and iron chelate) were applied to the irrigation solution as needed and water was added on a regular basis. Supplementary lighting was provided with 1,000 watt metal halide lamps elevated as needed. The plants were used for the test when they reached the first to the fourth stage of true leaves.
The treatments consisted of the 4-amino-3-chloro-5-fluor-6- (4-chloro-2-fluor-3-methoxy-phenyl) pyridine-2-carboxylic acid or esters (Compound A) each one formulated as a SC (suspension concentrate), and several herbicidal components alone and in combination. Compound A forms were applied on an acid equivalent basis.
Forms of compound A (compound of formula I) tested include: Acid of Compound A
n-Butyl Ester of Compound A Benzyl Ester of Compound A
Other herbicidal components were applied on an active ingredient basis and included photosynthesis-inhibiting propanyl herbicides II (PSII) formulated as Stam® M4 EC, bentazon-sodium formulated as Basagran®, atrazine formulated as atrazine 90 WDG, bromoxynil oc- ester tanoate formulated as Buctril®, symmetrine (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 on the rates that are tested, the concentration of active ingredient or acid equivalent in the formulation and an applied volume of 12 mL at a rate of 187 L / ha.
For treatments comprised of formulated compounds, the measured quantities of compounds were placed individually in 25 ml glass bottles and diluted in a volume of 1.25% (v / v) oil for concentrated Agri-Dex® cultures to obtain 12X solutions of stock. If a test compound did not readily dissolve, the mixture was heated and / or sonicated. The applied solutions were prepared by adding an appropriate amount of each stock solution (for example, 1 mL) and diluted to the appropriate final concentrations with the addition of 10 mL of a 1.25% (v / v) aqueous culture oil mixture so that the final spray solutions contained 1.25 +/- 0.05% (v / v) of oil for concentrated culture.
For treatments comprised of technical compounds, the heavy quantities can be placed individually in 25 ml glass bottles and dissolved in a volume of acetone / DMSO 97: 3 v / v to obtain 12X stock solutions. If a test compound does not readily dissolve, the mixture can be heated and / or sonicated. The applied solutions can be prepared by adding an appropriate amount of each stock solution (eg 1 ml) and diluted to the appropriate final concentrations with the addition of 10 ml of a 1.5% (v / v) aqueous culture oil mixture ) so that the final spray solutions contain 1.25% (v / v) concentrated culture oil. When technical materials are used, concentrated stock solutions can be added to the spray solutions so that the final concentrations of acetone and DMSO of the applied solutions are 16.2% and 0.5%, respectively.
For treatments comprised of formulated and technical compounds, the heavy quantities of the technical materials were placed individually in 25 ml glass bottles and dissolved in a volume of acetone / DMSO 97: 3 v / v to obtain 12X stock solutions, and the quantities measurements of the formulated compounds were placed individually in 25 ml glass vials and diluted in a volume of 1.5% (v / v) concentrated culture oil or water to obtain 12X stock solutions. If a test compound did not readily dissolve, the mixture was heated and / or sonicated. The applied solutions were prepared by adding an appropriate amount of each stock solution (for example, 1 mL) and diluted to the appropriate final concentrations with the addition of an appropriate amount of a 1.5% (v / v) aqueous culture oil mixture ) so that the final spray solutions contained 1.25% (v / v) concentrated culture oil. As required, more water and / or acetone / DMSO 97: 3 v / v was added to individual applied solutions so that the final concentrations of acetone and DMSO of the applied solutions being compared were 8.1% and 0.25%, respectively .
All stock solutions and applied solutions were visually inspected for compound compatibility before application. The spray solutions were applied to the plant material with a raised mandari track sprayer equipped with 8002E nozzles calibrated to deliver 187 L / ha over an applied area of 0.503 m2 at a spray height of 18 to 20 inches (46 to 50 cm) above the height of the average plant canopy. The control plants were sprayed in the same way with the white solvent.
The treated plants and the control plants were placed in a greenhouse as described above and watered by sub-irrigation to prevent washing of the test compounds. After approximately 3 weeks, the condition of the test plants when compared to that of untreated plants was determined visually and marked on a scale of 0 to 100 percent where 0 corresponds to no injury and 100 corresponds to complete elimination. Colby's equation was used to determine the expected herbicidal effects of the mixtures (Colby, S.R. 1967. Calculation of the synergis-tic and antagonistic response of herbicide combinations. Weeds 15: 20-22.). The following equation was used to calculate the expected activity of mixtures containing two active ingredients, A and B: Expected = A + B - (A x B / 100) A = observed effectiveness of active ingredient A at the same concentration as used in the mixture. B = observed effectiveness of active ingredient B at the same concentration as used in the mixture.
The tested compounds, applied rates employed, plant species tested, and results are given in Tables 1-14.
Table 1. Synergistic Activity of Compound A Acid Herbicide Compositions applied to Foliar and Propanil in Weed Control in a Rice Growing System ._______________________________ Table 2. Synergistic Activity of Compound A Benzyl Ester and Propanyl Herbicide Compositions to Foliar in Weed Control in a Rice Growing System ._________________________________________ Table 3. Synergistic Activity of Composites of Compound A n-Butyl Ester and Propanyl Herbicides applied to Foliar in Weed Control in a Rice Growing System .
Table 4. Synergistic Activity of Compound A Acid and Bentazon-Sodium Herbicide Compositions Applied to Foliar in Weed Control in a Rice Growing System .__________________________ Table 5. Synergistic Activity of Herbicide Compositions of Benzyl Ester of Compound A and Bentazon-sodium applied to Foliar in Weed Control in a Rice Growing System ._____________________ Table 6. Synergistic Activity of Composites of Compound A n-Butyl Ester and Bentazon-Sodium applied to Foliar in Weed Control in a Rice Growing System .__________________________ i Table 7. Synergistic Activity of Compound A and Atrazine Herbicide Compositions applied to Foliar in Weed Control Common to Rice Growing Systems.
Table 8. Synergistic Activity of Compounds of Benzyl Ester Compounds A and Atrazine applied to Foliar in Weed Control Common to Rice Cultivation Systems ._____________________________________ Table 9. Synergistic Activity of Compounds of Benzyl Ester Compound A and Bromoxynil applied to Foliar in Weed Control Common to Rice Growing Systems .______________________________________ Table 10. Synergistic Activity of Herbicide Compositions Benzyl Ester of Compound A and Simetrina applied to Foliar in Weed Control Common to Rice Growing Systems.
Table 11. Synergistic Activity of Compounds of Benzyl Ester Herbicides of Compound A and Simazine applied to Foliar in Weed Control Common to Rice Cultivation Systems.
Table 12. Synergistic Activity of Compounds of Benzyl Ester Herbicides of Compound A and Cyanazine applied to Foliar in Weed Control Common to Rice Cultivation Systems.
Table 13. Synergistic Activity of Herbicide Compositions Benzyl És-ter of Compound A and Ioxynil applied to Foliar in Weed Control Common to Rice Cultivation Systems.
Table 14. Synergistic Activity of Herbicide Compositions Benzyl És-ter of Compound A and Hexazinone applied to Foliar in Weed Control Common to Rice Cultivation Systems .________________________________ BRAPPBrachiaria platyphylla (Griseb). Nashcapim brachiaria, latifoliate COMBECommelina benghalensis L.trapoeraba, Bengalese CYPIRCyperus would L.junquinho, rice CYPESCyperus esculentus L.tiririca, yellow ECHCGEchinochloa crusgalli (L). Beauv.grass-capybara ECHC0Echinochloa colona (L). Linkcapim-jaú IPOHEIpomoea hederacea Jacq.ipomeia, ivyleaf LEFCHLeptochloa chinensis (L). Neessprangletop, Chinese g ae / ha = grams of acid equivalent per hectare g ai / ha = grams of active ingredient per hectare Obs = observed value Exp = expected value as calculated by the Colby equation DAA = days after application Example II. Evaluation of herbicide mixtures applied to weed control water in Transplanted Rice.
The seeds of weeds or nuts of the desired test plant species were planted in drenched soil (mud) prepared by mixing a crumbled, non-sterile mineral soil (mud 50.5 percent, clay 25.5 percent and sand 24 percent, with a pH of approximately 7.6 and an organic matter content of approximately 2.9 percent) and water in a 1: 1 volumetric ratio. The prepared sludge was dispensed in 365 ml aliquots in unperforated 453 g (16 oz) plastic pots. with a surface area of 86.59 square centimeters (cm2) leaving a head space of 3 centimeters (cm) in each pot. The sludge was left to dry overnight before planting or transplanting. The rice seeds were planted in the Sun Gro MetroMix® 306 planting mix, which typically has a pH of 6.0 to 6.8 and an organic matter content of approximately 30 percent, in plastic plug trays. The seedlings in the second or third stage of the growth leaf were transplanted into 840 ml_ of the mud contained in non-perforated plastic pots 907 g (32 oz). with a surface area of 86.59 cm2 4 days before herbicide application. The rice paddy was created by filling the head space 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 to 22 days in a greenhouse with a photoperiod of approximately 14 h that was maintained at approximately 29Ό during the day and 26 * Ό during the night. The nutrients were added as Osmocote® (19: 6: 12, N: P: K + minor nutrients) in 2 g per 453 g (16 oz) pot and 4 g per 907 g (32 oz) pot. Water was added on a regular basis to keep the paddy from flooding, and supplementary lighting was provided with 1,000 watt metal halide lamps elevated as needed. The plants were used for the test when they reached the first to the fourth stage of true leaves.
Treatments consisted of 4-amino-3-chloro-5-fluor-6- (4-chloro-2-fluor-3-methoxy-phenyl) pyridine-2-carboxylic acid (compound A) each as a SC (suspension concentrate) and various herbicidal components alone and in combination. Compound A forms were applied on an acid equivalent basis.
Forms of compound A (compound of formula I) tested include: Acid of Compound A
n-Butyl Ester of Compound A Benzyl Ester of Compound A
Other herbicidal components were applied on an active ingredient basis and included photosystem II (PSII) inhibitors propanil formulated as Stam® 4M EC, bentazon-sodium formulated as Basagran® and simetrine (technical grade material).
The treatment requirements for each compound or component of the herbicide were calculated based on the rates being tested, the concentration of active ingredient or acid equivalent in the formulation, an applied volume of 2 ml_ per component per pot and an applied area of 86.59 cm2 per pot.
For formulated compounds, a measured quantity was placed in an individual 100 or 200 mL glass vial and dissolved in a volume of 1.25% (v / v) of concentrated oil for cultivation of Agri-Dex® to obtain solutions of application. If the test compound did not readily dissolve, the mixture was heated and / or sonicated.
For technical-class compounds, a heavy amount was placed in a 100 to 200 ml individual glass bottle and dissolved in a volume of acetone to obtain concentrated stock solutions. If the test compound did not readily dissolve, the mixture was heated and / or sonicated. The concentrated stock solutions obtained were diluted with an equivalent volume of an aqueous mixture containing 2.5% (v / v) concentrated culture oil so that the final applied solutions contained 1.25% (v / v) concentrated culture oil. .
The applications were made by injection with a pipettor of appropriate quantities of the solutions applied, individually and sequentially, in the aqueous layer of the rice field. Control plants were treated in the same way with the white solvent. The applications were made so that all the treated plant material received the same concentrations of acetone and concentrated oil for culture.
The treated plants and the 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 when compared to that of untreated plants was determined visually and marked on a scale of 0 to 100 percent where 0 does not correspond to any injury or growth inhibition and 100 corresponds to complete elimination . Colby's equation was used to determine the expected herbicidal effects of the mixtures (Colby, S.R. 1967. Calculation of the synergis-tic and antagonistic response of herbicide combinations. Weeds 15: 20-22.). The following equation was used to calculate the expected activity of mixtures containing two active ingredients, A and B: Expected = A + B - (A x B / 100) A = observed effectiveness of active ingredient A at the same concentration as used in the mixture. B = observed effectiveness of active ingredient B in the same concentration as used in the mixture.
Some compounds tested, applied rates employed, plant species tested, and results are given in Tables 15-20.
Table 15. Synergistic Activity of Water Applications of Compound A and Propanyl Herbicide Compositions in Weed Control in a Rice Growing System .________________________________ Table 16. Synergistic Activity of Water Applications of Benzil Ester Herbicide Compositions of Compound A and Propanil in Weed Control in a Rice Growing System .___________________________ Table 17. Synergistic Activity of Water Applications of Compound A Acid and Bentazon-Sodium Compositions in Weed Control in a Weed Control System Rice cultivation.
Table 18. Synergistic Activity of Water Applications of Compounds of Benzyl Ester of Compound A and Bentazon-Sodium in Weed Control in a Rice Growing System .__________________ Table 19. Synergistic Activity of Water Applications of Herbicide Compositions of Compound A n-Butyl Ester and Bentazon-sodium in Weed Control in a Rice Growing System.
Table 20. Synergistic Activity of Water Applications of Compounds of Benzyl Ester Compound A and Symmetry in Weed Control in a Rice Cultivation System ._____________________________ CYPROCyperus rotundus L.tiririca, purple ECHCGEchinochloa crusgalli (L). Beauv.capim-capybara E C RE REchinochloa oryzoides (Ard). Fritschwatergrass, early FMWFimbristylis miliacea (L). False tiny vahl, globe LEFCHLeptochloa chinensis (L). Neessprangletop, Chinese SCPMASchoenoplectus maritimus (L). Bleachclubrush, mar g ae / ha = grams of acid equivalent per hectare g ai / ha = grams of active ingredient per hectare Obs = observed value Exp = expected value as calculated by the Colby equation DAA = days after application Example III. Evaluation of Herbicidal Activity After Mixture Mixtures in Cereal Cultures in the Greenhouse.
The seeds of the desired test plant species were planted in the Sun Gro MetroMix® 306 planting mix, which typically has a pH of 6.0 to 6.8 and an organic matter content of approximately 30 percent, in plastic pots with a surface area of 103.2 square centimeters (cm2). When required to ensure good germination and healthy plants, a fungicide treatment and / or other chemical or physical treatment was applied. The plants were grown for 7 to 36 days in a greenhouse with a photoperiod of approximately 14 hours that was maintained at approximately 18 ° C during the day and approximately 17 ° C at night. Nutrients and water were added on a regular basis and supplementary lighting was provided with 1,000 watt metal halide lamps elevated as needed. The plants were used for the test when they reached the second or third stage of true leaves.
The treatments consisted of benzyl ester of 4-amino-3-chloro-5-fluor-6- (4-chloro-2-fluor-3-methoxy-phenyl) pyridine-2-carboxylic acid (Compound A), formulated as a SC, a second cereal herbicide alone and then both in combination.
Forms of compound A (compound of formula I) tested include: Compound A benzyl ester
Other herbicidal components were applied on an active ingredient basis and included PSII inhibiting herbicides.
The measured aliquots of the benzyl ester of 4-amino-3-chloro-5-fluoro-6- (4-chloro-2-fluoro-3-methoxy-phenyl) pyridine-2-carboxylic acid (Compound A) were placed in 25 milliliter (mL) glass bottles and diluted in a volume of 1.25% (v / v) Agri-Dex® culture oil to obtain stock solutions. Compound requirements are based on an applied volume of 12 mL at a rate of 187 liters per hectare (L / ha). The spray solutions of the second herbicide for cereals and mixtures of experimental compounds were prepared by adding the stock solutions to the appropriate amount of the dilution solution to form 12 ml spray solution with active ingredients in two- and three-way combinations. The formulated compounds were applied to the plant material with a raised mandari track sprayer equipped with an 8002E nozzle calibrated to deliver 187 L / ha over an applied area of 0.503 square meters (m2) at a spray height of 18 inches (46 cm) the above of the medium vegetable canopy. The control plants were sprayed in the same way with the white solvent.
The treated plants and the control plants were placed in a greenhouse as described above and watered by sub-irrigation to prevent washing of the test compounds. After 20-22 days, the condition of the test plants when compared to that of the control plants was determined visually and marked on a scale of 0 to 100 percent where 0 corresponds to no injury and 100 corresponds to complete elimination. Colby's equation was used to determine the expected herbicidal effects of the mixtures (Colby, S.R. 1967. Calculation of the synergis-tic and antagonistic response of herbicide combinations. Weeds 15: 20-22.). The following equation was used to calculate the expected activity of mixtures containing two active ingredients, A and B: Expected = A + B - (A x B / 100) A = observed effectiveness of active ingredient A at the same concentration as used in the mixture. B = observed effectiveness of active ingredient B at the same concentration as used in the mixture.
The compounds tested, applied rates employed, plant species tested, and results are given in Tables 21 to 24.
Table 21. Synergistic Activity of Compounds of Benzyl Ester Compounds A and Metribuzin applied to Foliar in Weed Control in a Cereal Growing System .___________________________________ Table 22. Synergistic Activity of Compounds of Benzyl Ester Compound A and Isoproturon applied to Foliar in Weed Control in a Cereal Growing System.
Table 23. Synergistic Activity of Compounds of Benzyl Ester of Compound A and Bentazon-sodium applied to Foliar in Weed Control in a Cereal Growing System .____________________ Table 24. Synergistic Activity of Herbicide Compositions of Benzyl És-ter do Compound A and Bromoxynil applied to Foliar in Weed Control in a Cereal Growing System. AMAREAmaranthus retroflexus L.caruru, redroot BRSNWSrass / ca napus L.colza, oleaginous (winter) CΗEALChenopodium album L.lambsquarters, common GALAPGalium aparine L.aparina, catchweed IPOHEIpomoea hederacea Jacq.ipomeia, ivyleaf KCHSCKia scopia. Schrad.kochia LAMPÜLamium purpureum L.lâmio, purple SASKRSalsola tragus L.cardo, russian SETFASetaria faberi Herrm.capim-fox-tail, giant SINARSinapis arvensis L.mustarda, wild VERPEVeron / Persian Poir.Veronica, persian ge / persian ge / persian ge = grams of acid equivalent per hectare g ai / ha = grams of active ingredient per hectare Obs = observed value Exp = expected value as calculated by the Colby DAA equation = days after application Example IV. Pre-evaluation of herbicidal mixtures applied to weed control soil The seeds or nuts of the desired test plant species were planted in a soil matrix prepared by mixing a loam soil (32 percent mud, 23 percent clay and sand 45 percent, with a pH of approximately 6.5 and an organic matter content of approximately 1.9 percent) and limestone sand in an 80 to 20 ratio. The soil matrix was contained in plastic pots with a volume of 1 room and a surface area of 83.6 square centimeters (cm2).
The treatments consisted of benzyl ester of 4-amino-3-chloro-5-fluor-6- (4-chloro-2-fluor-3-methoxy-phenyl) pyridine-2-carboxylic acid (compound A) formulated as a SC (suspension concentrate) and various herbicidal components alone and in combination. Compound A forms were applied on an acid equivalent basis.
The forms of tested compound A (compound of formula I) include: Compound A benzyl ester
Other herbicidal components were applied on an active ingredient or acid equivalent basis and included PSII inhibiting herbicides, atrazine formulated as atrazine® 90WDG, metribuzin formulated as Metribuzin 75DF, simazine formulated as Princep Caliper 90, tebutiuron formulated as Spike 80DF, cyanazine (technical grade material), hexazinone (technical grade material), linuron (technical grade material), terbuti-lazine (technical grade material), and diuron formulated as Diuron 4L.
Treatment requirements were calculated based on the rates that are tested, the concentration of active ingredient or acid equivalent in the formulation and an applied volume of 12 mL at a rate of 187 L / ha.
For treatments comprised of formulated compounds, the measured quantities of compounds were placed individually in 25 ml glass bottles and diluted in a volume of 1.25% (v / v) Agri-Dex® concentrated culture oil (COC) to obtain 12X stock solutions. If a test compound did not readily dissolve, the mixture was heated and / or sonicated. The applied solutions were prepared by adding an appropriate amount of each stock solution (for example, 1 mL) and diluted to the appropriate final concentrations with the addition of 10 mL of a 1.25% (v / v) COC aqueous mixture to that the final spray solutions contained 1.25% (v / v) COC.
For treatments comprised of technical compounds, the heavy quantities 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 readily dissolve, the mixture can be heated and / or sonicated. The applied solutions can be prepared by adding an appropriate amount of each stock solution (for example, 1 ml) and diluted to the appropriate final concentrations with the addition of 10 ml of a 1.5% (v / v) aqueous COC mixture so that final spray solutions contain 1.25% (v / v) COC. When technical materials are used, concentrated stock solutions can be added to the spray solutions so that the final concentrations of acetone and DMSO of the applied solutions are 16.2% and 0.5%, respectively.
For treatments comprised of formulated and technical compounds, the heavy quantities of technical materials can be placed individually in 25 ml glass vials and dissolved in a volume of 97: 3 (v / v) acetone / DMSO to obtain 12X stock solutions, and the measured quantities of the formulated compounds can be placed individually in 25 ml glass bottles and diluted in a volume of 1.5% (v / v) COC or water to obtain 12X stock solutions. If a test compound does not readily dissolve, the mixture can be heated and / or sonicated. The applied solutions can be prepared by adding an appropriate amount of each stock solution (for example, 1 mL) and diluted to the appropriate final concentrations with the addition of an appropriate amount of a 1.5% (v / v) aqueous COC mixture to final spray solutions contain 1.25% (v / v) COC. As required, more water and / or acetone / DMSO 97: 3 (v / v) can be added to individual applied solutions so that the final concentrations of acetone and DMSO of the applied solutions being compared are 8.1% and 0.25 %, respectively.
All stock solutions and applied solutions were visually inspected for compound compatibility before application. The spray solutions were applied to the ground with a raised mandari runway sprayer equipped with 8002E nozzles calibrated to deliver 187 L / ha over an applied area of 0.503 m2 at a spray height of 18 inches (46 cm) above the average height of the Bowl. Control pots were sprayed in the same way with the white solvent.
The treated and control pots were placed in a greenhouse and watered from above 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 kept in a greenhouse with a photoperiod of approximately 14 hours that was kept at a-approximately 29Ό during the day and 260 during the night. The nutrients (Peters® Excel 15-5-15 5-Ca 2 mg) were applied to the irrigation solution as needed and water was added on a regular basis. Supplementary lighting was provided with 1,000 watt metal halide lamps elevated as needed. After approximately 4 weeks, the condition of the test plants when compared to that of untreated plants was determined visually and marked on a scale of 0 to 100 percent where 0 does not correspond to any injury or growth inhibition and 100 corresponds to complete elimination . Colby's equation was used to determine the expected herbicidal effects of the mixtures (Colby, S.R. 1967. Calculation of the synergis-tic and antagonistic response of herbicide combinations. Weeds 15: 20-22.). The following equation was used to calculate the expected activity of mixtures containing two active ingredients, A and B: Expected = A + B - (A x B / 100) A = observed effectiveness of active ingredient A at the same concentration as used in the mixture. B = observed effectiveness of active ingredient B at the same concentration as used in the mixture.
Some compounds tested, applied rates employed, plant species tested, and results are given in Tables 25-32.
Table 25. Synergistic Activity of Pre-Emergence Applications Applied to the Soil of Compounds of Benzyl Ester of Compound A and Atrazine in Weed Control _________________________________ Table 26. Synergistic Activity of Pre-Emergence Applications Applied to the Soil of Benzyl Herbicide Compositions Ester of Compound A and Metribuzin in Weed Control________________________________ Table 27. Synergistic Activity of Pre-emergence Applications Applied to Soil of Compositions of Benzyl Herbicides Ester of Compound A and Simazine in Weed Control_______________________________ Table 28. Synergistic Activity of Pre- Applications Emergence Applied to Soil from Compounds of Benzyl Ester of Compound A and tebutiuron in Weed Control_____________________________ Table 29. Synergistic Activity of Pre-Emergence Applications Applied to Soil from Ben Herbicide Compositions zil Compound A Ester and Cyanazine in Weed Control________________________________ Table 30. Synergistic Activity of Pre-emergence Applications Applied to Soil Compounds of Benzyl Compound A Ester and Linuron in Weed Control_________________________________ Table 31. Synergistic Activity of Pre Applications -Surgence Applied to Soil from Compounds of Benzyl Ester Compound A and Terbutilazine in Weed Control________________________ Table 32. Synergistic Activity of Pre-Emergence Applications Applied to Soil Compounds of Benzyl Ester Compound A and Diuron in Control of Weed__________________ ABUTHAbutilon theophrasti Medik.juta-da-china BRAPPSrac / i / ar / a platyphylla (Groseb). Nash or Urochloa platyphylla (Nash) R.D. Webstercapim brachiaria, ECHCGEchinochloa crus-galli (L). P. Beauv.capim-capybara ECHCOEchinochloa colonum (L). Linkcapim-jaú IPOHEIpomoea hederacea (L). Jacq.ipomeia, ivyleaf SETFASetaria faberi Herrm.capim-fox-tail, giant SETVISetaria viridis (L). Beauv.capim-fox-tail, green XANSTXanthium strumarium L.carrapicho, common g ae / ha = grams of acid equivalent per hectare g ai / ha = grams of active ingredient per hectare Obs = observed value Exp = expected value as calculated by Colby equation DAA = days after application Example V. Post-soil evaluation Foliar-applied herbicidal mixtures for general weed control Seeds or root cuts of the desired test plant species were planted in the Sun Gro MetroMix® 306 planting mixture , which typically has a pH of 6.0 to 6.8 and an organic matter content of approximately 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 fungicide treatment and / or other chemical or physical treatment was applied. The plants were grown for 9-30 days in a greenhouse with an approximate photoperiod of 14 hours that was maintained at approximately 28 ° C during the day and 24 ° C at night. Nutrients and water were added on a regular basis and supplementary lighting was provided with 1,000 watt metal halide lamps elevated as needed. The plants were used for the test when they reached stage BBCH11 to leaf BBCH14.
The treatments consisted of the benzyl ester of 4-amino-3-chloro-5-fluor-6- (4-chloro-2-fluor-3-methoxy-phenyl) pyridine-2-carboxylic acid (Compound A), formulated as a SC and a tebutiuron-containing herbicide (Spike® 80DF). A measured aliquot of Compound A was placed in a 25 ml glass vial (mL) and diluted in a volume of distilled water or concentrated oil for culture Agri-dex 1.25% volume / volume (v / v) to obtain stock solutions. Compound requirements are based on an applied volume of 12 mL at a rate of 187 liters per hectare (L / ha). Spray solutions of the herbicide containing glyphosate and mixtures of experimental compounds were prepared by adding the stock solutions to the appropriate amount of the dilution solution to form 12 mL of spray solution with active ingredients in two-way combinations. The formulated compounds were applied to the plant material with a raised mandari track sprayer equipped with 8002E nozzles calibrated to deliver 187 L / ha over an applied area of 0.503 square meters (m2) at a spray height of 18 inches (43 cm) above of the medium vegetable canopy. The control plants were sprayed in the same way with the white solvent.
The treated plants and the control plants were placed in a greenhouse as described above and watered by sub-irrigation to prevent washing of the test compounds. After approximately 14 days, the condition of the test plants, when compared to that of the control plants, was determined visually and marked on a scale from 0 to 100 percent where 0 corresponds to no injury and 100 corresponds to complete elimination. Colby's equation was used to determine the expected herbicidal effects of the mixtures (Colby, S.R. 1967. Calculation of the synergis-tic and antagonistic response of herbicide combinations. Weeds 15: 20-22.). The following equation was used to calculate the expected activity of mixtures containing two active ingredients, A and B: Expected = A + B - (A x B / 100) A = observed effectiveness of active ingredient A at the same concentration as used in the mixture. B = observed effectiveness of active ingredient B at the same concentration as used in the mixture.
Some compounds tested, applied rates employed, plant species tested, and results are given in Table 33.
Table 33. Synergistic Activity of Herbicidal Compositions of Benzyl Ester of Compound A and Spike 80DF (tebutiuron) applied to Foliar formulated in concentrated oil for culture 1.25% (v / v) in water in General Weed Control ._________________________________________________________ ECHCGEchinochloa crus. -galli L.capim-capybara C RARCirsium arvense (L). Scop.cardo, Canada BRSNNBrassica napus L.colza, CYPESCyperus esculentus L.tiririca berry, yellow

权利要求:
Claims (11)
[1]
1. Synergistic herbicide composition comprising a herbicidally effective amount of (a) a compound of formula (I) or an agriculturally acceptable salt or ester thereof and (b) at least one compound, or an agriculturally acceptable salt, carboxylic acid, salt carboxylate or ester thereof, selected from the group consisting of ofatrazine, bentazon, bentazon-sodium, bromoxynil, chlorotoluron, cyanazine, diuron, hexazinone, ioxynil, isoproturon, linuron, metibenzuron, metribuzin, propanyl, pyridine, sididine, pyridine, pyridine, sididine, pyridine, sididine , tebutiuron, and terbuthylazine.
[2]
A composition according to claim 1, wherein (a) is the compound of the formula (I), a C1-4 alkyl ester of the compound of the formula (I) or a benzyl ester of the compound of the formula (I ).
[3]
The composition of any one of claims 1 to 2, further comprising an agriculturally acceptable adjuvant or vehicle.
[4]
The composition of any one of claims 1 to 3, further comprising an herbicide phytoprotectant.
[5]
5. Method of controlling undesirable vegetation that comprises contact with vegetation or the locus thereof or application to soil or water to prevent the emergence or growth of vegetation of a herbicidally effective amount of (a) a compound of formula (I) or a agriculturally acceptable salt or ester thereof and (b) is at least one compound, or a salt, carboxylic acid, agriculturally acceptable carboxylate salt or ester thereof, selected from the group consisting of: atrazine, bentazon, bentazon-sodium, bromoxynil , chlorotoluron, cyanazine, diuron, hexazinone, ioxynil, isoproturon, linuron, metibenzuron, metribuzin, propanil, pyridate, siduron, simazine, symmetry, tebutiuron and terbu-tilazine.
[6]
A method according to claim 5, wherein (a) is the compound of the formula (I), a C1-4 alkyl ester of the compound of the formula (I) or a benzyl ester of the compound of the formula (I) .
[7]
Method according to any one of claims 5 to 6, wherein the undesirable vegetation is controlled in rice directly sown, sown in water and transplanted, cereals, wheat, barley, oats, rye, sorghum, corn / maize, cane sugar, sunflower, rapeseed, canola, beet, soy, cotton, pineapple, pasture, pasture, natural pasture, fallow, lawn, tree and vine orchards, aquatic, large plantations, industrial vegetation management (IVM) or strips of easement (ROW).
[8]
Method according to any one of claims 5 to 7, in which (a) and (b) are applied in the pre-emergence of the weed or the crop.
[9]
A method according to any one of claims 5 to 8, wherein the undesirable vegetation is controlled in cultures tolerant to glyphosphate, 5-enolpyruvylshikimato-3-phosphate (EPSP) synthase, glufosin-to inhibitor glutamine synthetase, dicamba, phenoxy-auxin, pyridyloxy-auxin, synthetic auxin, auxin transport inhibitor, aryloxyphenoxypropionate, cyclohexanedione, phenylpyrazoline, acetyl CoA carboxylase (ACCase) inhibitor, imidazolinone, sulfonylurea, trifluorohydride, pyrimidine, pyrimidine, pyridine -phonylaminocarbonyltriazolinone, acetolactate synthase (ALS) inhibitors or acetohydroxy synthase (AHAS) inhibitor, 4-hydroxyphenyl-pyruvate dioxige-nase (HPPD) inhibitor, phyteno desaturase inhibitor, carcinoid inhibitor PP (protoporphyride inhibitor) ), cellulose biosynthesis inhibitor, mitosis inhibitor, microtubule inhibitor, very long chain fatty acid inhibitor, acid biosynthesis inhibitor fat and lipid, photosystem I inhibitor, photosystem II inhibitor, triazine or bromoxynil.
[10]
A method according to claim 9, wherein the tolerant culture has multiple or stacked traits conferring tolerance to multiple herbicides or multiple modes of action.
[11]
A method according to any one of claims 5 to 10, wherein the undesirable vegetation comprises a herbicide-resistant or tolerant weed.

类似技术:

---

公开号 | 公开日 | 专利标题

---

ES2717034T3|2019-06-18|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- | pyridine-2-carboxylic acid

---

ES2713171T3|2019-05-20|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- | pyridine-2-carboxylic acid or a derivative of this and microtubule inhibiting herbicides

---

ES2717283T3|2019-06-20|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- | pyridine-2-carboxylic acid or a derivative thereof and herbicides inhibitors of VLCFA synthesis and synthesis of fatty acids / lipids

---

ES2727658T3|2019-10-17|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- | pyridine-2-carboxylic acid

---

CA2879960C|2020-10-27|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6-| pyridine-2-carboxylic acid or a derivative thereof and synthetic auxin herbicides

---

ES2713175T3|2019-05-20|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- | pyridine-2-carboxylic acid

---

CA2880090C|2020-09-29|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6-|pyridine-2-carboxylic acid or a derivative thereof and certain ps ii inhibitors

---

ES2724213T3|2019-09-09|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- | pyridine-2-carboxylic acid

---

TWI612895B|2018-02-01|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6-|pyridine-2-carboxylic acid or a derivative thereof and bromobutide, daimuron, oxaziclomefone or pyributicarb

---

KR102102824B1|2020-04-22|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6-| pyridine-2-carboxylic acid

---

RU2632969C2|2017-10-11|Herbicidal compositions containing 4-amino-3-chloro-5-fluoro-6-| pyridine-2-carboxylic acid

---

BR102013018660A2|2015-03-03|HERBICIDE COMPOSITIONS UNDERSTANDING 4-AMINO-3-CHLORINE-5-FLUORO-6- | PYRIDINE-2-CARBOXYLIC ACID, OR HALOSULFURON, ERABOSPURBURIUR, AND PIROSPHUROSURAR

---

BR102013018526B1|2020-02-04|synergistic herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- | pyridine-2-carbo-xylic or butyl or benzyl ester thereof and a dimethoxy- pyrimidine and its derivatives, and method for controlling undesirable vegetation

---

BR102013018511A2|2015-03-03|HERBICIDE COMPOSITIONS UNDERSTANDING 4-AMINO-3-CHLORINE-5-FLUOR-6- | PYRIDINE-2-CARBOXYLIC ACID OR BISHESIDESIS INHIBITORS

---

BR102013018482B1|2020-02-04|herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- | pyridine-2-carboxylic acid or a derivative thereof and auxin transport inhibitors, and method to control unwanted vegetation

---

BR102014005580A2|2015-10-06|herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- | pyridine-2-carboxylic acid or its derivative and insecticides

---

BR102014001780A2|2015-08-25|Herbicidal compositions comprising 4-amino-3-chloro-6- | pyridine-2-carboxylic acid or a derivative thereof and propyzamide

---

BR102014001750B1|2019-12-24|herbicidal compositions comprising 4-amino-3-chloro-6- | pyridine-2-carboxylic acid or a derivative thereof and certain triazolopyrimidine sulfonamides, and method for controlling undesirable vegetation

---

BR112021008350A2|2021-08-03|compositions comprising halauxifene and other herbicides and methods thereof

---

OA17322A|2016-05-23|Herbicidal compositions comprising 4-amino3-chloro-5-fluoro-6-| pyridine-2-carboxylic acid or a derivative thereof and microtubule inhibiting herbicides.

---

OA17280A|2016-04-29|Herbicidal compositions comprising 4-amino3-chloro-5-fluoro-6-| pyridine-2-carboxylic acid or a derivative thereof and certain PS II inhibitors.

同族专利:

---

公开号 | 公开日

---

EP2877022A2|2015-06-03|

---

UY34935A|2014-02-28|

---

WO2014018393A3|2015-07-16|

---

JP6378177B2|2018-08-22|

---

WO2014018393A2|2014-01-30|

---

KR20150038263A|2015-04-08|

---

PH12015500145B1|2015-03-16|

---

IN2015DN01380A|2015-07-03|

---

PT2877022T|2019-07-11|

---

CL2015000166A1|2015-04-24|

---

SA113340745B1|2015-07-07|

---

AU2013293306A1|2015-03-05|

---

AR091898A1|2015-03-11|

---

DK2877022T3|2019-08-05|

---

CO7200267A2|2015-02-27|

---

US20140031222A1|2014-01-30|

---

US8912121B2|2014-12-16|

---

MX2015001144A|2016-03-21|

---

CN104936449A|2015-09-23|

---

TW201408202A|2014-03-01|

---

TWI599317B|2017-09-21|

---

KR102102423B1|2020-04-20|

---

EP2877022B1|2019-05-01|

---

CN104936449B|2018-03-02|

---

CA2880090C|2020-09-29|

---

IL236852A|2020-02-27|

---

JP2015527328A|2015-09-17|

---

BR102013018536B1|2020-11-24|

---

HK1209970A1|2016-04-15|

---

AU2013293306B2|2017-04-20|

---

ZA201501144B|2017-08-30|

---

UA115991C2|2018-01-25|

---

SG11201500528SA|2015-02-27|

---

RU2015105952A|2016-09-10|

---

HUE045281T2|2019-12-30|

---

CA2880090A1|2014-01-30|

---

IL236852D0|2015-03-31|

---

MY172890A|2019-12-13|

---

PH12015500145A1|2015-03-16|

---

RU2639885C2|2017-12-25|

---

EP2877022A4|2016-05-18|

---

PL2877022T3|2019-10-31|

引用文献:

---

公开号 | 申请日 | 公开日 | 申请人 | 专利标题

---

---

RS20080076A|2005-08-24|2009-07-15|Pioneer Hi-Brend International Inc.,|Compositions providing tolerance to multiple herbicides and methods of use thereof|

---

EP1973881B1|2006-01-13|2009-10-28|Dow Agrosciences LLC|6--4-aminopicolinates and their use as herbicides|

---

UA94351C2|2007-08-27|2011-04-26|ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи|Synergistic herbicidal composition comprising certain pyridine or pyrimidine carboxylic acids and certain herbicides for cereals and rice|

---

EP2191719A1|2008-11-29|2010-06-02|Bayer CropScience AG|Herbicide safener combination|

---

RU2012118395A|2009-10-07|2013-11-20|ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи|SYNERGIC FUNGICIDAL COMPOSITION CONTAINING 5-FLUORCYTOSINE FOR THE STRUGGLE AGAINST FUNGAL DISEASES OF GRAIN CROPS|

---

UA106786C2|2010-02-19|2014-10-10|ДАУ АГРОСАЙЄНСІЗ ЕлЕлСі|An herbicide/fungicide composition containing a pyridine carboxylic acid a fungicide|

---

JP6129077B2|2010-11-05|2017-05-17|ダウ アグロサイエンシィズ エルエルシー|Control of phenoxyalkanoic acid herbicide-tolerant weeds with 4-amino-3-chloro-6- pyridine-2-carboxylic acid and its salts or esters|

---

TWI596088B|2011-01-25|2017-08-21|陶氏農業科學公司|Arylalkyl esters of 4-amino-6-picolinates and 6-amino-2--4-pyrimidinecarboxylates and their use as herbicides|

---

BR102012027933A2|2011-11-01|2015-11-17|Dow Agrosciences Llc|stable pesticide compositions|

---

US8846570B2|2012-07-24|2014-09-30|Dow Agrosciences, Llc.|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6-pyridine-2-carboxylic acid or a derivative thereof and microtubule inhibiting herbicides|

---

US8906826B2|2012-07-24|2014-12-09|Dow Agrosciences, Llc.|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- pyridine-2-carboxylic acid or a derivative thereof and imidazolinones|

---

US8906825B2|2012-07-24|2014-12-09|Dow Agrosciences, Llc.|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- pyridine-2-carboxylic acid or a derivative thereof and triazolopyrimidine sulfonamides|

---

US8871680B2|2012-07-24|2014-10-28|Dow Agrosciences, Llc.|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- pyridine-2-carboxylic acid or a derivative thereof and a di-methoxy-pyrimidine and derivatives thereof|

---

US8901035B2|2012-07-24|2014-12-02|Dow Agrosciences, Llc.|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- pyridine-2-carboxylic acid or a derivative thereof and cellulose biosynthesis inhibitor herbicides|

---

US8895470B2|2012-07-24|2014-11-25|Dow Agrosciences, Llc.|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- pyridine-2-carboxylic acid or a derivative thereof and glyphosate or glufosinate|

---

US8871681B2|2012-07-24|2014-10-28|Dow Agrosciences Llc|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- pyridine-2-carboxylic acid or a derivative thereof and certain sulfonylureas|

---

US8912120B2|2012-07-24|2014-12-16|Dow Agrosciences, Llc.|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- pyridine-2-carboxylic acid or a derivative thereof and synthetic auxin herbicides|

---

US8841233B2|2012-07-24|2014-09-23|Dow Agrosciences Llc|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- pyridine-2-carboxylic acid or a derivative thereof and 4-hydroxyphenyl-pyruvate dioxygenase inhibitors|

---

US8889591B2|2012-07-24|2014-11-18|Dow Agrosciences, Llc.|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6-pyridine-2-carboxylic acid or a derivative thereof and bromobutide, daimuron, oxaziclomefone or pyributicarb|

---

US8791048B2|2012-07-24|2014-07-29|Dow Agrosciences Llc|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- pyridine-2-carboxylic acid or a derivative thereof and clomazone|

---

US8883682B2|2012-07-24|2014-11-11|Dow Agrosciences, Llc.|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6-pyridine-2-carboxylic acid or a derivative thereof and auxin transport inhibitors|

---

US8809232B2|2012-07-24|2014-08-19|Dow Agroscience Llc|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- pyridine-2-carboxylic acid or a derivative thereof and halosulfuron, pyrazosulfuron and esprocarb|

---

US8916499B2|2012-07-24|2014-12-23|Dow Agrosciences, Llc.|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- pyridine-2-carboxylic acid or a derivative thereof and a protoporphyrinogen oxidase inhibitor|

---

US8796177B2|2012-07-24|2014-08-05|Dow Agrosciences Llc|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6-pyridine-2-carboxylic acid or a derivative thereof and acetyl-CoA carboxylase inhibitors|

---

US9644469B2|2012-07-24|2017-05-09|Dow Agrosciences Llc|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- pyridine-2-carboxylic acid or a derivative thereof and VLCFA and lipid synthesis inhibiting herbicides|UA94351C2|2007-08-27|2011-04-26|ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи|Synergistic herbicidal composition comprising certain pyridine or pyrimidine carboxylic acids and certain herbicides for cereals and rice|

---

US8841233B2|2012-07-24|2014-09-23|Dow Agrosciences Llc|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- pyridine-2-carboxylic acid or a derivative thereof and 4-hydroxyphenyl-pyruvate dioxygenaseinhibitors|

---

US9644469B2|2012-07-24|2017-05-09|Dow Agrosciences Llc|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- pyridine-2-carboxylic acid or a derivative thereof and VLCFA and lipid synthesis inhibiting herbicides|

---

US8883682B2|2012-07-24|2014-11-11|Dow Agrosciences, Llc.|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6-pyridine-2-carboxylic acid or a derivative thereof and auxin transport inhibitors|

---

US8796177B2|2012-07-24|2014-08-05|Dow Agrosciences Llc|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6-pyridine-2-carboxylic acid or a derivative thereof and acetyl-CoA carboxylaseinhibitors|

---

US8889591B2|2012-07-24|2014-11-18|Dow Agrosciences, Llc.|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6-pyridine-2-carboxylic acid or a derivative thereof and bromobutide, daimuron, oxaziclomefone or pyributicarb|

---

US8912120B2|2012-07-24|2014-12-16|Dow Agrosciences, Llc.|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- pyridine-2-carboxylic acid or a derivative thereof and synthetic auxin herbicides|

---

US8916499B2|2012-07-24|2014-12-23|Dow Agrosciences, Llc.|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- pyridine-2-carboxylic acid or a derivative thereof and a protoporphyrinogen oxidase inhibitor|

---

US8871681B2|2012-07-24|2014-10-28|Dow Agrosciences Llc|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- pyridine-2-carboxylic acid or a derivative thereof and certain sulfonylureas|

---

US8871680B2|2012-07-24|2014-10-28|Dow Agrosciences, Llc.|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- pyridine-2-carboxylic acid or a derivative thereof and a di-methoxy-pyrimidine and derivatives thereof|

---

US8906826B2|2012-07-24|2014-12-09|Dow Agrosciences, Llc.|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- pyridine-2-carboxylic acid or a derivative thereof and imidazolinones|

---

US8809232B2|2012-07-24|2014-08-19|Dow Agroscience Llc|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- pyridine-2-carboxylic acid or a derivative thereof and halosulfuron, pyrazosulfuron and esprocarb|

---

US8901035B2|2012-07-24|2014-12-02|Dow Agrosciences, Llc.|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- pyridine-2-carboxylic acid or a derivative thereof and cellulose biosynthesis inhibitor herbicides|

---

US8846570B2|2012-07-24|2014-09-30|Dow Agrosciences, Llc.|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6-pyridine-2-carboxylic acid or a derivative thereof and microtubule inhibiting herbicides|

---

US8791048B2|2012-07-24|2014-07-29|Dow Agrosciences Llc|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- pyridine-2-carboxylic acid or a derivative thereof and clomazone|

---

US8906825B2|2012-07-24|2014-12-09|Dow Agrosciences, Llc.|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- pyridine-2-carboxylic acid or a derivative thereof and triazolopyrimidine sulfonamides|

---

US8895470B2|2012-07-24|2014-11-25|Dow Agrosciences, Llc.|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- pyridine-2-carboxylic acid or a derivative thereof and glyphosate or glufosinate|

---

US9730445B2|2013-03-15|2017-08-15|Dow Agrosciences Llc|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- pyridine-2-carboxylic acid or a derivative thereof and fungicides|

---

AP2015008776A0|2013-03-15|2015-09-30|Dow Agrosciences Llc|Safened herbicidal compositions including pyridine-2-carboxylic acid derivatives for use in corn |

---

US8841234B1|2013-03-15|2014-09-23|Dow Agrosciences, Llc.|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- pyridine-2-carboxylic acid or a derivative thereof and fungicides|

---

BR102014018731A2|2014-07-30|2016-05-31|Fmc Química Do Brasil Ltda|pre- and post-emergence broad spectrum herbicidal formulation containing triazolinones in combination with urea pesticides and methods for weed control and crop yield|

---

BR102014018735A2|2014-07-30|2016-05-31|Fmc Química Do Brasil Ltda|dual mode herbicide formulation for weed control, method for controlling unwanted weeds and method for increasing crop yield|

---

US10455836B2|2014-09-15|2019-10-29|Dow Agrosciences Llc|Synergistic weed control from applications of pyridine carboxylic acid herbicides and photosystem II inhibitors|

---

CN106857563A|2016-12-31|2017-06-20|山东滨农科技有限公司|A kind of Herbicidal composition for rice field of containing chlorine fluorine pyridine ester|

---

CN107593714B|2017-10-31|2020-07-28|青岛海知誉信息科技有限公司|Weeding composition containing chloropyridyl ester and triazine compound and application thereof|

---

CN110896954A|2019-11-21|2020-03-24|安徽众邦生物工程有限公司|Weeding composition containing halauxifen-methyl and simetryn|

---

GB202004460D0|2020-03-27|2020-05-13|Upl Corporation Ltd|Herbical composition|

法律状态:
2018-05-15| B03A| Publication of a patent application or of a certificate of addition of invention [chapter 3.1 patent gazette]|

---

2018-05-29| B06F| Objections, documents and/or translations needed after an examination request according [chapter 6.6 patent gazette]|

---

2018-09-25| B06A| Patent application procedure suspended [chapter 6.1 patent gazette]|

---

2019-03-12| B06A| Patent application procedure suspended [chapter 6.1 patent gazette]|

---

2019-12-10| B06A| Patent application procedure suspended [chapter 6.1 patent gazette]|

---

2020-04-07| B06A| Patent application procedure suspended [chapter 6.1 patent gazette]|

---

2020-07-07| B09A| Decision: intention to grant [chapter 9.1 patent gazette]|

---

2020-11-24| B16A| Patent or certificate of addition of invention granted [chapter 16.1 patent gazette]|Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 19/07/2013, OBSERVADAS AS CONDICOES LEGAIS. |

优先权:

---

申请号 | 申请日 | 专利标题

---

US201261675089P| true| 2012-07-24|2012-07-24|

---

US61/675,089|2012-07-24|

---

US13/840,488|US8912121B2|2012-07-24|2013-03-15|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6-pyridine-2-carboxylic acid or a derivative thereof and certain PS II inhibitors|

---

US13/840,488|2013-03-15|

---