WO2007050090A1 - Compositions herbicides - Google Patents

Compositions herbicides Download PDF

Info

Publication number
WO2007050090A1
WO2007050090A1 PCT/US2005/039443 US2005039443W WO2007050090A1 WO 2007050090 A1 WO2007050090 A1 WO 2007050090A1 US 2005039443 W US2005039443 W US 2005039443W WO 2007050090 A1 WO2007050090 A1 WO 2007050090A1
Authority
WO
WIPO (PCT)
Prior art keywords
weight
poe
herbicidal composition
esters
herbicidal
Prior art date
Application number
PCT/US2005/039443
Other languages
English (en)
Inventor
Alkesander E. Karczewski
Jane Qing Liu
Evelyn Jean Taylor
Original Assignee
Valent U.S.A. Corporation
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Valent U.S.A. Corporation filed Critical Valent U.S.A. Corporation
Priority to PCT/US2005/039443 priority Critical patent/WO2007050090A1/fr
Publication of WO2007050090A1 publication Critical patent/WO2007050090A1/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
    • A01N35/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/50—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A01N43/18—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with sulfur as the ring hetero atom

Definitions

  • the present invention relates to herbicidal compositions. More particularly, the present invention relates to improved adjuvant-containing formulations suitable as postemergent herbicides which improve the efficacy of herbicides.
  • the formulation comprises a mixture of one or more herbicidal compounds, a polyoxyalkylene nonionic surfactant having a hydrophilic-lipophilic balance (HLB) of from 10 to about 14, an anionic surfactant selected from the dialkyl metal sulfosuccinates and the metal alkylbenzene sulfonates, optionally a low foaming polyoxyalkylene nonionic surfactant having an HLB of less than 10, and a lower alkanol ester of a long chain fatty acid.
  • HLB hydrophilic-lipophilic balance
  • An object of the present invention is to provide improved herbicidal compositions and methods of use which exhibit excellent herbicidal efficacy and chemical stability.
  • an herbicidal composition comprising (a) an effective amount of an herbicidal cyclohexanedione oxime compound or agriculturally acceptable salt or ester thereof; (b) one or more esters of a fatty acid; and (c) one or more nonionic surfactant; wherein said composition substantially excludes anionic surfactants selected from the dialkylmetalsulfosuccinates and the metal alkylaromatic sulfonates.
  • an anionic surfactant other than a dialkylmetalsulfosuccinate or a metal alkylaromatic sulfonate and (e) a hydrocarbon solvent can be used.
  • the present invention provides an herbicidal composition
  • an herbicidal composition comprising (a) 10 to 30% by weight of clethodim; (b) 30 to 80% by weight of a mixture of the methyl esters of C 16-Cl 8 fatty acids; (c) 7 to 12% by weight of the nonionic surfactant; and optionally (d) 5 to 50% by weight of an aromatic hydrocarbon solvent.
  • the present invention provides an herbicidal composition
  • an herbicidal composition comprising (a) 10 to 30% by weight of clethodim; (b) 30 to 80% by weight of a mixture of the methyl esters of C 16-C 18 fatty acids; (c) 1 to 5% by weight of the nonionic surfactant; (d) 1 to 3% by weight of POE (5) tallow amine ether sulfate; and optionally (e) 5 to 50% by weight of an aromatic hydrocarbon solvent.
  • the present invention provides methods for controlling the growth of vegetation, comprising applying to the vegetation an effective amount of the herbicidal composition described above.
  • the herbicidal compositions of the present invention offer several advantages, including, for example, one or more of the following: they are chemically stable formulations, they do not require the addition of a crop oil concentrate, they provide superior control of susceptible weed species, provide increased speed of herbicide absorption and herbicide symptoms, they result in increased speed of glyphosate absorption, and they can be tank mixed with other herbicides without a decrease in weed control.
  • the herbicidal ingredient of the present invention is an herbicidal compound having a cyclohexanedione oxime structure.
  • Certain cyclohexanedione oximes are known in the art as having excellent herbicidal activity against a variety of post-emergent grasses in a variety of environments. Typical examples include clethodim, sethoxydim, alloxydim, cycloxydim, butroxydim, tralkoxydim, tepraloxydim, and profoxydim. Cyclohexanedione oximes can be obtained on the market. For example, clethodim is provided by Valent U.S.A.
  • cyclohexanedione oximes are clethodim and sethoxydim. Most preferred is clethodim.
  • the active ingredient can be employed in several technical forms such as Clethodim Technical (Valent U.S.A.
  • the content of the herbicidal cyclohexanedione oxime compound in the herbicidal compositions is preferably about 1 to 40% by weight, more preferably 3 to 30% by weight, and most preferably 10 to 30% by weight.
  • the esters of a fatty acid are preferably C1-C8 alkyl (e.g. methyl, ethyl, isopropyl, butyl, isobutyl, octyl) esters of a fatty acid.
  • the fatty acids can be saturated or unsaturated organic monobasic acids such as palmitic acid, myristic acid, stearic acid, lauric acid or oleic acid.
  • the carbon numbers of the fatty acids are preferably 12 to 22. Typical non-limiting examples include methyl oleate, methyl palmitate, isopropyl myristate, octyl laurate, isopropyl palmitate, and butyl stearate.
  • the preferred esters of a fatty acid are a mixture comprised predominantly of the methyl esters of C 16-Cl 8 fatty acids.
  • the C 16-C 18 fatty acid methyl ester mixture used in the herbicidal formulations tested in the Examples set forth herein was CE-1618 (C16 23-32%, C18 65-75%, primarily methyl oleate), available from Proctor and Gamble or AGNIQUE® ME 181-U (typically Cl 6 10%, Cl 8 84%, primarily methyl oleate), available from Cognis Corporation.
  • esters of fatty acids include but are not limited to CE- 1695, CE- 1897, SE- 1885, also available from Proctor and Gamble; other AGNIQUE® ME and AE products, available from Cognis Corporation; STEPAN C-65 and C-68 and KESSCO® IPP, IPM and BS, available from Stepan Company; and PRIOLUBE® 1530 and 1400, available from Uniqema.
  • the content of the esters of a fatty acid in the herbicidal compositions of the present invention is preferably about 10 to 90% by weight, more preferably 10 to 80% by weight, even more preferably 20 to 80% by weight, and most preferably 30 to 80% by weight.
  • the ratio of the esters of a fatty acid to the herbicidal ingredient is preferably 0.5 : 1 to 25:1, more preferably 0.8:1 to 12:1, and most preferably 1 :1 to 6:1.
  • Suitable nonionic surfactants include but are not limited to polyoxyethylene (POE) derivatives of tallow or plant oils, POE sorbitan esters, ethylene oxide-propylene oxide (EO- PO) block polymers, POE alkylphenols, polyoxyalkylene polyarylethers, ethoxylated alcohols, POE fatty acid esters, alkyl polyglycosides and alkylpolysaccharides, POE fatty amines, and polymeric surfactants.
  • the HLB of the nonionic surfactant is preferably about 5.0 to 18.0.
  • the POE derivatives of tallow or plant oils may be hydrogenated.
  • the plant oils include but are not limited to castor oil, rapeseed oil and linseed oil.
  • a preferred plant oil is castor oil.
  • the POE castor oil surfactants used in the herbicidal formulations tested in the Examples set forth herein were AGNIQUE® CSO-40 (POE (40) castor oil, HLB 13), AGNIQUE® CSO-30 (POE (30) castor oil, HLB 11.8), and AGNIQUE® CSO-16 (POE (16) castor oil, HLB 8.6), available from Cognis Corporation.
  • POE derivatives of tallow or plant oils include but are not limited to AGNIQUE® SBO, RSO and other CSO products also available from Cognis Corporation; NINEX® MT-603, MT-610 and MT-615 and TOXIMUL® 8240, 8241, 8243, and 8244, available from Stepan Company; EMULPON® CO 200, 904, and CO-360, available from Akzo Nobel; EMULSOGEN® EL 360, EL 400, EL-719, and HCO 040, available from Clariant Corporation; and ALKAMULS® EL-620, OR-40, and EL-719, available from Rhodia.
  • the POE sorbitan esters are preferably the ethoxylated sorbitan esters of fatty acids.
  • the fatty acid may be derived from animal or vegetable sources. Typical examples include but are not limited to POE sorbitan monotallate, POE sorbitan monooleate, POE sorbitan trioleate, POE sorbitan monostearate, POE sorbitan tristearate, POE sorbitan monomyristate, and POE sorbitan monolaurate.
  • a preferred POE sorbitan ester is POE (20) sorbitan monooleate.
  • the POE (20) sorbitan monooleate used in the herbicidal formulations tested in the Examples set forth herein was AGNIQUE® SMO 20-U (HLB 15) available from Cognis Corporation.
  • Other suitable POE sorbitan esters include but are not limited to AGNIQUE® SML, SMS, STS, and other SMO products, also available from Cognis Corporation; ARMOTAN® SMO 20, available from Akzo Nobel; TOXIMUL® SEE-340 and 341, available from Stepan Company; and ALTOX® 80 and 8916TF, TWEEN® 20, 40, 60, 65, 80, 81, and 85 available from Uniqema.
  • Typical examples of EO-PO block polymers include but are not limited to block copolymers of ethylene oxide and propylene oxide, EO-PO alkylphenol block polymers, EO- PO butanol block polymers (polyoxyethylene-polyoxypropylene monobutyl ether), and EO- PO ethylenediamine block polymers.
  • the EO-PO block polymer used in the herbicidal formulations tested in the Examples set forth herein was PLURONIC® L92 (block copolymer of ethylene oxide and propylene oxide, average molecular weight 3650, HLB 6).
  • EO-PO block polymers are other surfactants from the PLURONIC® L and P series, available from BASF Corporation; TOXIMUL® 8320 and 8323, available from Stepan Company; ATLAS® G-5000 and SYNPERONIC® PE series, available from Uniqema; AGNIQUE® BP 4-3103, and BP NP-1530, available from Cognis Corporation; ETHYLAN® NS 500 K and NS 500 LQ, available from Akzo Nobel; TERGITOLTM XD, XH, XJ, available from The Dow Chemical Company; and ANTAROXTM 724/P, SC/167, F-108, and P-104, available from Rhodia.
  • POE alkylphenols include but are not limited to POE nonylphenol, POE octylphenol, POE tributylphenol, POE dinonylphenol, and POE dodcylphenol.
  • the POE alkylphenols used in the herbicidal formulations tested in the Examples set forth herein were MAKON® 4 (POE (4) nonylphenol, HLB 9) and MAKON® 8 (POE (8) nonylphenol, HLB 12), available from Stepan Company.
  • POE alkylphenols are MAKON® 10, 12, 14 and 30, and MAKON® OP-9, also available from Stepan Company; SYNPERONIC® NP series, available from Uniqema; ARKOP AL® N series, EMULSOGEN® 10, and SAPOGENAT® T 040, T060, T 080, and T I lO, available from Clariant Corporation; AGNIQUE® NP and OP series, available from Cognis Corporation; WITCONOL® NP series, available from Akzo Nobel; and IGEP ALTM CO, CA, DM and RC series, available from Rhodia.
  • polyoxyalkylene polyarylethers include but are not limited to polyoxyethylene (POE) polyoxypropylene (POP) tristyrylphenols, and POE tristyrylphenols.
  • POE polyoxyethylene
  • POP polyoxypropylene
  • POE tristyrylphenols POE tristyrylphenols.
  • Other suitable examples of polyoxyalkylene polyarylethers are EMULSOGEN® TS 160, available from Clariant Corporation; AGNIQUE® TSP 16, available from Cognis Corporation; and SOPROPHOR® BSU and CY/8, available from Rhodia.
  • Typical examples of ethoxylated alcohols include but are not limited to POE C6-12 alcohol, POE C9-12 alcohol, POE C12-15 alcohol, POE C16-18 alcohol, POE lauryl alcohol, POE oleyl alcohol, POE stearyl alcohol, POE isodecylalcohol, and POE tridecylalcohol.
  • the ethoxylated alcohol used in the herbicidal formulations tested in the Examples set forth herein was BIO-SOFT® N25-7 (POE (7) C12-C15 alcohol, HLB 12.2), available from Stepan Company.
  • ethoxylated alcohols are BIO-SOFT® N, EN, and E series, and MAKON® DA and TD series, also available from Stepan Company; BRIJ® 35, 56, and 78, ATLOX® MBA 11/6, 13/5, and 13/20, RENEX® 30, 31 and 36, and SYNPERONIC® A3, A5, Al 1, 91/4 and 91/10, available from Uniqema; GENAPOL® LA and O series, available from Clariant Corporation; AGNIQUE® FOH series, available from Cognis Corporation; ETHYLAN® OX 91-8, SN 70, 1204, 048, and 087, available from Akzo Nobel; and RHODASURFTM DA-530, DA-630, L-4 and RHODASURFTM BC series, available from Rhodia.
  • POE fatty acid esters include POE dioleate, POE monolaurate, POE monooleate, POE dioleate, POE monostearate, POE coconut oil fatty acid ester, and POE tall oil fatty acid ester.
  • the POE fatty acid ester used in the herbicidal formulations tested in the Examples set forth herein was AGNIQUE® PEG 600ML (POE monolaurate, where the approximate molecular weight (MW) of the POE group is 600, HLB 14.8), available from Cognis Corporation.
  • POE fatty acid esters are AGNIQUE® 200MO, 400MO, 400 MS, and 660 MS, also available from Cognis Corporation; MYRJ® 45, 49,51, and 53, available from Uniqema; MAPEG® 200 ML, 400 DO, 400 MO, 400 MOT, and 600 MS, available from BASF Corporation; and STEP AN® PEG series, available from Stepan Company.
  • alkyl polyglycosides and alkyl polysaccharides include AGNIQUE® PG 8105-U, AGNIQUE® PG 8107-U, AGNIQUE® PG 8166, AGNIQUE® PG 9166, and AGNIQUE® PG 266, available from Cognis Corporation; TritonTM BG-IO and CG-110, available from The Dow Chemical Company; and ATPLUS® 438 and 452, available from Uniqema.
  • POE fatty amines include POE tallow amine, POE cocoamine, POE oleylamine, and POE stearyl amine.
  • suitable POE fatty amines are TOXIMUL® TA-2, TA-5, TA-8, TA-IO, and TA-15, available from Stepan Company; AGNIQUE® CAM-2, CAM-IO, CAM-15, CAM-20, OAM-30, TAM-IO, TAM-15, TAM-20, TAM-40, and SAM-50, available from Cognis Corporation; and RHODAMEENTM PN-430 and RHODAMEENTM TA-15 available from Rhodia.
  • Typical non-limiting examples of polymeric surfactants are ATLOX® 4912, 4913, and 4914, available from Uniqema; and polyvinylpyrrolidone polymers such as AGRIMER 15, 30, and 60, available from International Specialty Products.
  • Preferred nonionic surfactants include block copolymers of propylene oxide and ethylene oxide, POE (16) castor oil, POE (30) castor oil, POE (40) castor oil, POE (4) nonylphenol, POE (8) nonylphenol, POE (21)/ POP (4) tristyrylphenol, POE (20) sorbitan mono-oleate, POE (7) C12-C15 alcohol, and POE monolaurate.
  • the preferred content of the nonionic surfactant varies depending on whether the herbicidal composition comprises anionic surfactant. If anionic surfactant is used, the content of the nonionic surfactant is preferably about 0.2 to 12% by weight, more preferably 0.5 to 8% by weight, most preferably 1 to 5% by weight. If anionic surfactant is not used, the content of the nonionic surfactant is preferably about 1 to 20% by weight, more preferably 3 to 15% by weight, most preferably 7 to 12% by weight.
  • any agriculturally acceptable anionic surfactant can be added as an optional component, except that the composition substantially excludes anionic surfactants selected from the dialkylmetalsulfosuccinates and the metal alkylaromatic sulfonates, hi this embodiment, "substantially excludes” means that such anionic surfactants are not present in amounts designed to have some advantageous effect (see, e.g., U.S. Pat. No. 5,084,087), as opposed to being present in trace or minor amounts for no significant practical purpose.
  • Suitable optional anionic surfactants include but are not limited to ether sulfates and phosphate esters.
  • ether sulfates include but are not limited to sodium or ammonium salts of fatty alcohol ether sulfates, sodium or ammonium salts of alkylaryl ether sulfates, sodium or ammonium salts of ethoxylated alkylaryl ether sulfates, POE tallow amine alkylphenol ether sulfates, and POE tallow amine alcohol ether sulfate.
  • ether sulfates include SOPROPHOR DSS/15 and 4D 384, available from Rhodia; WITCOLATE PA, available from Akzo Nobel; AGNIQUE® SNT-45, SLES-270-U, and SLES-330C, available from Cognis Corporation; and TOXIMUL® TANS-5, TANS-6, TANS-8, TANS-15, TAAS-5, TAAS-8, TAAS-15, TANS 5B, TANS 8B, and TANS 15B, available from Stepan Company.
  • Typical non-limiting examples of the phosphate esters include POE tridecyl ether phosphate, POE lauryl ether phosphate, POE nonylphenol phosphate, POE isodecyl ether phosphate, POE dinonylphenol phosphate, and POE 2-ethylhexyl ether phosphate.
  • Commercially available phosphate esters include RHOD AFACTM BG-510, RE-410, RE-610, RM-510, RM-710, RS-410, and RS-610, available from Rhodia; ATPHOSTM 3226, 3232,
  • a preferred anionic surfactant is POE (5) tallow amine ether sulfate.
  • the content of the optional anionic surfactant in the herbicidal composition is preferably about 0.1 to 5% by weight, more preferably 0.5 to 5% by weight, and most preferably 1 to 3% by weight.
  • the optional hydrocarbon solvent is not restricted so long as it can dissolve the herbicidal cyclohexanedione oxime compound.
  • Suitable hydrocarbon solvents include but are not limited to aliphatic hydrocarbon solvents, white spirits and mineral spirits (mixtures of paraffins, cycloparaffins and aromatic hydrocarbons), and aromatic hydrocarbon solvents.
  • Typical non-limiting examples of the aliphatic hydrocarbon solvents include isoparaffinic solvents, normal paraffmic solvents, dearomatized hydrocarbon solvents, and aliphatic mineral spirits.
  • Aromatic hydrocarbon solvents include pentane; cyclopentane; hexane; heptane; isohexane; isopentane; naphtha; ISOP ARTM M 5 L, P, and V, NORP ARTM 12, 13, 14, and 15, and EXXSOLTM D80, D95, DlOO, and D120, all available from ExxonMobil Chemical; and SHELLSOLTM D40, D60, and D80, and SHELLSOLTM TD, OMS, TC, TM, all available from Shell Chemicals.
  • Aromatic hydrocarbon solvents are preferred, and are readily available from a number of sources.
  • Examples include but are not limited to xylene; phenylxylyl ethane; HISOL® SAS-296 (a mixture of 1 -phenyl- 1-xylyl ethane and 1 -phenyl- 1-ethylphenyl ethane), available from Nippon Petroleum Company; CACTUS SOLVENT® HP-DMN (containing 80% of dimethylnaphthalene) and CACTUS SOLVENT® P-IOO (alkylbenzene having carbon number of 9 to 10), available from Nikko Petrochemical Company; SOLVESSOTM 100, 150, and 200, AROMATIC 100, 150, and 200, NAPHTHALENE DEPLETED AROMATIC 150 and 200, and ULTRA-LOW NAPHTHALENE AROMATIC 150 and 200 (aromatic hydrocarbons), available from ExxonMobil Chemical; and HI-SOL® 10 and HI-SOL® 15
  • Preferred aromatic hydrocarbon solvents are AROMATIC 150 and SOLVESSOTM
  • AROMATIC 150 was used in the herbicidal formulations tested in the Examples set forth herein.
  • the content of the optional hydrocarbon solvent is preferably about 5 to 85% by weight, and most preferably 5 to 50% by weight.
  • the herbicidal composition optionally comprises another solvent, and/or auxiliary components such as antioxidant (e.g., propyl gallate, ascorbyl palmitate, butylated hydroxytoluene, or butylated hydroxyanisole), thickener, antifoaming agent, perfume, dyestuff, and emollient (e.g. cetyl alcohol and stearyl alcohol).
  • antioxidant e.g., propyl gallate, ascorbyl palmitate, butylated hydroxytoluene, or butylated hydroxyanisole
  • thickener e.g., propyl gallate, ascorbyl palmitate, butylated hydroxytoluene, or butylated hydroxyanisole
  • antifoaming agent e.g., perfume, dyestuff, and emollient
  • emollient e.g. cetyl alcohol and stearyl alcohol.
  • Examples of other solvents include but are not limited to 2-ethylhexanol, propylene glycol, ethylene glycol, diethylene glycol, and glycerin.
  • the content of the additional solvent in the herbicidal composition is preferably about 0.5 to 4% by weight.
  • the content of the propyl gallate in the herbicidal composition is preferably about 0.01 to 1% by weight, more preferably 0.05 to
  • Preferred embodiments of the herbicidal composition of the present invention include 0.2 to 0.3% propyl gallate by weight.
  • the content of the cetyl alcohol in the herbicidal composition is preferably about 0.1 to 5% by weight, more preferably 0.5 to 3% by weight.
  • Preferred embodiments of the herbicidal composition of the present invention include 1 % cetyl alcohol by weight.
  • the herbicidal composition of the present invention can be prepared by mixing (a) an herbicidal cyclohexanedione oxime compound or agriculturally acceptable salt or ester thereof as an herbicidal ingredient, (b) one or more esters of a fatty acid, (c) one or more nonionic surfactant, (d) optionally an anionic surfactant that is not a dialkylmetalsulfosuccinate or a metal alkylaromatic sulfonate, (e) optionally a hydrocarbon solvent, and optionally other solvents, auxiliaries and so on. There are no specific mixing condition requirements, and the components do not need to be added in any particular order.
  • antioxidant such as propyl gallate
  • the herbicidal compositions of the present invention are typically utilized as emulsif ⁇ able concentrates, namely they are diluted with water to give an emulsion and applied to weeds, especially graminaceous weeds such as barnyardgrass (Echinochloa crus-galli), green foxtail (Setaria viridis), giant foxtail (Setariafaberi), large crabgrass (Digitaria sanguinalis), annual bluegrass (Poa annu ⁇ ), blackgrass ⁇ Alopecurus myosuroides), oats (Avena sativ ⁇ ), wild oats (Avenafatu ⁇ ), johnsongrass (Sorghum halepense), quackgrass (Agropyron repens), downy brome (Bromus tectorum), and bermudagrass (Cynodon dactylo ⁇ ), in broad-leaf crop (e.g.
  • barnyardgrass Echinochloa crus-galli
  • soybean cotton, sugarbeet, peanut, alfalfa, potatoes, flax, canola, sunflowers, fruiting vegetables, legume crops, cranberries, cucurbit crops, head and stem brassica crops, leafy brassica crops, lettuce crops, mustard seed, onion, garlic, shallots, leaks, root vegetables, rhubarb, spinach, strawberry, sweet potato, and many other crops) fields.
  • the application dosage is generally about 0.063 to 0.250 pounds active ingredient per acre (about 70 to 280 grams of active ingredient per hectare) in the amount of the herbicidal cyclohexanedione oxime compound.
  • One of ordinary skill in the art could determine an appropriate application dosage, which may vary with crop, objective weeds, weather conditions and so on.
  • the dilution of the herbicidal composition can be used for aerial application by helicopter, plane or radio-controlled helicopter.
  • One of the advantages of the herbicidal composition of the present invention is its ability to achieve commercially acceptable weed control (>90%) without the need for tank mixing with crop oil concentrates, crop oil concentrate blends, nonionic surfactant adjuvants, or ammonium sulfate.
  • these materials may be desirable to increase efficacy, or may be required by a tank-mix partner.
  • glyphosate formulations commonly require the addition of ammonium sulfate.
  • crop oil concentrates, crop oil concentrate blends, or nonionic surfactant adjuvants examples include AGRI-DEX®, DYNE-AMIC®, and INDUCE®, available from Helena Chemical Corporation; SILWET® L-77, available from Loveland Industries; PRIME OIL® and PRIME OIL® EV , DESTINY®, and PREFERENCE®, manufactured by Agriliance; HERBIMAX® and MSO® CONCENTRATE, manufactured by Loveland Industries; BRITZ O/S BLEND, manufactured by Britz Fertilizers, Incorporated; and MOR- ACT®, manufactured by Wilbur-Ellis.
  • the present invention overcomes those limitations with respect to glyphosate formulations, and also with respect to other herbicides such as but not limited to CADRE® (active ingredient imazapic, available from BASF Corporation), STORMTM (active ingredients acifluorfen and bentazon, available from United Phosphorus, Incorporated), and COBRA® (active ingredient lactofen, available from Valent U.S.A. Corporation).
  • CADRE® active ingredient imazapic, available from BASF Corporation
  • STORMTM active ingredients acifluorfen and bentazon, available from United Phosphorus, Incorporated
  • COBRA® active ingredient lactofen, available from Valent U.S.A. Corporation
  • herbicidal formulations of the present invention are tested for their efficacy against a variety of common weeds, hi many cases, comparisons are made to similar commercially available herbicidal formulations which contain clethodim as the active ingredient.
  • One such commercially available herbicidal formulation used for comparison purposes is SELECT® 2 EC, a product of Valent U.S.A. Corporation.
  • the numerical values represent the percentage of weed control, or percent kill of the various species.
  • the use rate of the herbicidal formulations is expressed in terms of pounds of active ingredient per acre (Ib ai/A).
  • Several herbicidal formulations of the present invention were tested in the following examples. These herbicidal formulations are defined as follows:
  • ROUNDUP READY® corn was used in this experiment as the target weed species. A single application was made to actively growing corn which had reached 12 to 24 inches in height. All herbicide treatments included ammonium sulfate at 2.5 lbs per acre and were made using identical equipment and application methods.
  • Clethodim is known to provide excellent control of a wide array of grassy weeds; however the speed of visual activity generally requires up to 10 days.
  • the clethodim formulations of the present invention provide much quicker visual control symptoms than SELECT® 2 EC, providing the user with assurance that the product is working.
  • clethodim formulations of the present invention are superior to SELECT® 2 EC, because they can be used at 80% or less of the amount of active ingredient per acre and achieve at least equivalent, and in many cases more complete, control of susceptible weeds species.
  • Example 4 Significance of Invention: The clethodim formulations of the present invention are superior to SELECT® 2 EC, because they can be used at 80% or less of the amount of active ingredient per acre and achieve at least equivalent, and in many cases more complete, control of susceptible weeds species.
  • Table V illustrates that the enhanced clethodim formulations of the present invention are superior to SELECT® 2 EC because they do not require a crop oil concentrate (COC) adjuvant to provide commercially acceptable efficacy.
  • COC crop oil concentrate
  • ROUNDUP READY® corn was used in this experiment as the target weed species.
  • a single application was made to actively growing corn using 20 gallons of water per acre and applied with a tractor-mounted sprayer.
  • the SELECT® 2 EC treatments all contained COC at 25.6 oz/A.
  • the treatments using Formulations I, K, and L of the present invention contained a nonionic surfactant (NIS) at 6.4 oz/A, but did not contain any COC. All herbicide treatments included ammonium sulfate at 3.4 lbs per acre and were made using identical equipment and application methods.
  • NIS nonionic surfactant
  • Clethodim is known to provide excellent control of a wide array of grassy weeds; however, the effectiveness of clethodim is generally dependent on the addition of a COC adjuvant, which may not always be a desirable addition to the spray program, and is in fact prohibited on many glyphosate labels.
  • the clethodim formulations of the present invention provide equivalent or better efficacy compared to SELECT® 2 EC without the addition of a COC adjuvant.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne une composition herbicide améliorée qui exclut sensiblement les tensioactifs anioniques choisis parmi les sulfosuccinates de dialkyle de métal et les sulfonates de métal alkylaromatiques. Cette composition herbicide améliorée comprend (a) une quantité efficace d'un composé herbicide de cyclohexanedione-oxime ou d'un sel ou ester de la dite substance acceptable sur le plan agricole, (b) un ou plusieurs esters d'un acide gras, (c) un ou plusieurs tensioactifs non ioniques, et, en option, un ou les deux (d) tensioactifs anioniques autres qu'un sulfosuccinate de dialkyle de métal ou qu'un sulfonate de métal alkylaromatique, et (e) un solvant d'hydrocarbure. La présente invention prévoit en outre des procédés pour contrôler le développement de la végétation par l'application sur celle-ci de ladite composition.
PCT/US2005/039443 2005-10-28 2005-10-28 Compositions herbicides WO2007050090A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/US2005/039443 WO2007050090A1 (fr) 2005-10-28 2005-10-28 Compositions herbicides

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US2005/039443 WO2007050090A1 (fr) 2005-10-28 2005-10-28 Compositions herbicides

Publications (1)

Publication Number Publication Date
WO2007050090A1 true WO2007050090A1 (fr) 2007-05-03

Family

ID=37968094

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2005/039443 WO2007050090A1 (fr) 2005-10-28 2005-10-28 Compositions herbicides

Country Status (1)

Country Link
WO (1) WO2007050090A1 (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2002719A1 (fr) * 2007-06-12 2008-12-17 Bayer CropScience AG Composition d'adjuvants à base d'huile
WO2010021404A3 (fr) * 2008-08-19 2011-02-17 Ishihara Sangyo Kaisha, Ltd. Procédé de lutte contre la dégradation d'ingrédients actifs chimiques agricoles
WO2011103619A1 (fr) * 2010-02-23 2011-09-01 Innovative Chemical Services Pty Ltd Adjuvant sous forme d'émulsion pour herbicides
CN103238597A (zh) * 2012-02-10 2013-08-14 中国中化股份有限公司 肟草酮组合物
WO2016196130A1 (fr) 2015-06-04 2016-12-08 Arysta Lifescience North America, Llc Formulations d'oxime de dioxyde de cyclohexane stabilisées par agent tensio-actif
CN107251895A (zh) * 2017-06-08 2017-10-17 深圳诺普信农化股份有限公司 喷雾助剂及其制备与应用
WO2019197619A1 (fr) 2018-04-13 2019-10-17 Bayer Cropscience Aktiengesellschaft Concentré de matières en suspension à base d'huile
WO2019197621A1 (fr) 2018-04-13 2019-10-17 Bayer Cropscience Aktiengesellschaft Concentré de matières en suspension à base d'huile
WO2020053763A1 (fr) 2018-09-14 2020-03-19 Adama Agan Ltd. Composition d'oxime de cyclohexanedione stabilisée
EP3970492A1 (fr) 2020-09-21 2022-03-23 UPL Corporation Limited Compositions herbicides stables

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040018940A1 (en) * 2002-07-18 2004-01-29 Erwin Hacker Combinations of cyclohexanedione oxime herbicides and safeners

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040018940A1 (en) * 2002-07-18 2004-01-29 Erwin Hacker Combinations of cyclohexanedione oxime herbicides and safeners

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2002719A1 (fr) * 2007-06-12 2008-12-17 Bayer CropScience AG Composition d'adjuvants à base d'huile
WO2008151725A1 (fr) * 2007-06-12 2008-12-18 Bayer Cropscience Ag Nouvelle composition d'adjuvant à base d'huile
JP2010530365A (ja) * 2007-06-12 2010-09-09 バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト 新規な油性アジュバント組成物
WO2010021404A3 (fr) * 2008-08-19 2011-02-17 Ishihara Sangyo Kaisha, Ltd. Procédé de lutte contre la dégradation d'ingrédients actifs chimiques agricoles
WO2011103619A1 (fr) * 2010-02-23 2011-09-01 Innovative Chemical Services Pty Ltd Adjuvant sous forme d'émulsion pour herbicides
AU2011220319B2 (en) * 2010-02-23 2014-03-27 Innovative Chemical Services Pty Ltd Emulsion adjuvant for herbicides
US8975214B2 (en) 2010-02-23 2015-03-10 Innovative Chemical Services Pty Ltd Emulsion adjuvant for herbicides
CN103238597A (zh) * 2012-02-10 2013-08-14 中国中化股份有限公司 肟草酮组合物
JP2018517702A (ja) * 2015-06-04 2018-07-05 アリスタ ライフサイエンス ノース アメリカ， エルエルシー 界面活性剤で安定化されたシクロヘキサンジオキシドオキシム製剤
WO2016196130A1 (fr) 2015-06-04 2016-12-08 Arysta Lifescience North America, Llc Formulations d'oxime de dioxyde de cyclohexane stabilisées par agent tensio-actif
CN108347919A (zh) * 2015-06-04 2018-07-31 北美爱利思达生命科学有限责任公司 表面活性剂稳定的二氧化环己烷肟制剂
EP3310162A4 (fr) * 2015-06-04 2018-12-05 Arysta Lifescience North America LLC Formulations d'oxime de dioxyde de cyclohexane stabilisées par agent tensio-actif
AU2019203083B2 (en) * 2015-06-04 2020-11-05 Arysta Lifescience North America, Llc Surfactant-stabilized cyclohexanedioxide oxime formulations
CN107251895A (zh) * 2017-06-08 2017-10-17 深圳诺普信农化股份有限公司 喷雾助剂及其制备与应用
WO2019197619A1 (fr) 2018-04-13 2019-10-17 Bayer Cropscience Aktiengesellschaft Concentré de matières en suspension à base d'huile
WO2019197621A1 (fr) 2018-04-13 2019-10-17 Bayer Cropscience Aktiengesellschaft Concentré de matières en suspension à base d'huile
WO2020053763A1 (fr) 2018-09-14 2020-03-19 Adama Agan Ltd. Composition d'oxime de cyclohexanedione stabilisée
US20220030858A1 (en) * 2018-09-14 2022-02-03 Adama Agan Ltd. Stabilized cyclohexanedione oxime composition
US12089594B2 (en) * 2018-09-14 2024-09-17 Adama Agan Ltd. Stabilized cyclohexanedione oxime composition
EP3970492A1 (fr) 2020-09-21 2022-03-23 UPL Corporation Limited Compositions herbicides stables
WO2022058748A1 (fr) 2020-09-21 2022-03-24 UPL Corporation Limited Compositions herbicides stables

Similar Documents

Publication Publication Date Title
AU2005302428B2 (en) Herbicidal compositions
WO2007050090A1 (fr) Compositions herbicides
CN104244719B (zh) 包含脂肪酸烷基酯、脂肪酸酰胺、或甘油三脂肪酸酯的含水除草浓缩物及使用方法
JP2020169176A (ja) 天然油または石油由来の油を含有する殺有害生物剤の乳剤および使用方法
JP2017511364A (ja) パラフィン油を含む水性殺有害生物剤濃縮液および使用方法
CN101282641A (zh) 含有吡氟草胺的油悬浮液浓缩物
EA039812B1 (ru) Водная дисперсия гербицидных средств, способ её получения и её применение
Foy Adjuvants–current trends and technology
JP5395057B2 (ja) 水に懸濁可能な農薬組成物
WO2023228176A1 (fr) Composition herbicide comprenant de la thiencarbazone et du fluroxypyr
WO1994023578A1 (fr) Composition herbicide
WO2009134375A2 (fr) Nouvelles compositions de pyriproxyfène
CN110996660A (zh) 油分散性制剂
CN114745954B (zh) 液态农药组合物
US20230148591A1 (en) Use of oil based suspo-emulsion concentrates for reducing drift during spray application
EP0789510B1 (fr) Formulations de poudres mouillables
WO2024105660A1 (fr) Nouveaux systèmes de formulation d'herbicide tricétone
CA2204162C (fr) Formulations pour poudres mouillables
AU737739B2 (en) Wettable powder formulations
WO2022149077A1 (fr) Formulations d'azadirachtine et leur procédé de préparation et d'utilisation
CN116018067A (zh) 液体除草组合物
CN115915943A (zh) 除草剂组合物、制剂及其方法

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application
NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 05814901

Country of ref document: EP

Kind code of ref document: A1