WO2008073369A1 - Mélanges herbicides - Google Patents

Mélanges herbicides Download PDF

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Publication number
WO2008073369A1
WO2008073369A1 PCT/US2007/025224 US2007025224W WO2008073369A1 WO 2008073369 A1 WO2008073369 A1 WO 2008073369A1 US 2007025224 W US2007025224 W US 2007025224W WO 2008073369 A1 WO2008073369 A1 WO 2008073369A1
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Prior art keywords
cyclopropyl
methyl
chloro
amino
pyrimidinecarboxylate
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PCT/US2007/025224
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English (en)
Inventor
Gregory R. Armel
Wonpyo Hong
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E. I. Du Pont De Nemours And Company
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Publication of WO2008073369A1 publication Critical patent/WO2008073369A1/fr

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    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines

Definitions

  • This invention relates to herbicidal mixtures of certain pyrrolidine derivatives, their jV-oxides and salts, and to compositions comprising such mixtures, and methods for controlling undesirable vegetation.
  • R 1 is cyclopropyl optionally substituted with 1-5 R 5 , or phenyl optionally substituted with 1-3 R 7 ;
  • R 2 is ((O) j C(R 15 )(R 16 )) k R;
  • R is CO 2 H or a herbicidally effective derivative of CO 2 H;
  • R 3 is halogen, cyano, nitro;
  • R 4 is -N(R 24 )R 25 or -NO 2 ;
  • j is 0 or 1; and k is 0 or 1; provided that when k is 0, then j is 0; and
  • R 5 , R 7 , R 15 , R 16 , R 24 and R 25 are as defined in the disclosure.
  • this publication does not disclose the mixtures of the present invention or their surprising synergistic utility.
  • This invention is directed to a herbicidal mixture
  • a herbicidal mixture comprising (a) at least one herbicidal compound selected from pyrimidines of Formula 1 (including all geometric and stereoisomers), N-oxides, and salts thereof:
  • R 1 is cyclopropyl, 4-Br-phenyl or 4-Cl-phenyl; X is Cl or Br; and
  • R 2 is H, C 1 -C 14 alkyl, C2-C1 4 alkoxyalkyl, C 3 -C 14 alkoxyalkoxyalkyl, C 2 -C 14 hydroxyalkyl or benzyl;
  • R 3 is H, halogen, C 1 -C 6 alkyl, C 2 -C 6 alkoxyalkyl, C 3 -C 6 cycloalkyl or C 3 -C 8 cycloalkylalkyl;
  • R 4 is H, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkylcarbonyloxy, C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 hydroxyalkyl, phenoxycarbonyl or benzyloxycarbonyl; W is O or NR 5 ; R 5 is H, halogen, CN, C 1 -C 6 alkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 haloalkylcarbonyl,
  • G is a phenyl ring or 5- or 6-membered heteroaromatic ring, each ring optionally substituted with from 1 to 4 substiruents independently selected from R 6 ;
  • This invention also relates to a herbicidal composition
  • a herbicidal composition comprising a herbicidally effective amount of a mixture of the invention and at least one of a surfactant, a solid diluent or a liquid diluent.
  • This invention further relates to a method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of a mixture of the invention (e.g., as a composition described herein).
  • compositions, process, method, article, or apparatus that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, process, method, article, or apparatus.
  • alkyl includes straight-chain or branched alkyl, such as, methyl, ethyl, n-propyl, z-propyl, or the different butyl, pentyl or hexyl isomers.
  • Alkoxyalkyl denotes alkoxy substitution on alkyl.
  • alkoxyalkyl include CH 3 OCH 2 , CH 3 OCH 2 CH 2 , CH 3 CH 2 OCH 2 , CH 3 CH 2 CH 2 CH 2 OCH 2 and
  • Alkoxyalkoxy denotes alkoxy substitution on alkoxy.
  • Alkoxyalkoxyalkyl denotes alkoxyalkoxy substitution on alkyl.
  • alkoxyalkoxyalkyl include CH 3 OCH 3 OCH 2 , CH 3 OCH 3 OCH 2 CH 2 , CH 3 CH 2 OCH 3 OCH 2 and CH 3 OCH 3 CH 2 OCH 2 CH 2 .
  • Hydroalkyl denotes hydroxy substitution on alkyl. Examples of “hydroxyalkyl” include HOCH 2 CH 2 and HOCH 2 CH 2 CH 2 CH 2 .
  • stereoisomers in the mixtures of this invention can exist as one or more stereoisomers.
  • the various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers.
  • one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers.
  • N-oxides of heterocycles and tertiary amines are very well known by one skilled in the art including the oxidation of heterocycles and tertiary amines with peroxy acids such as peracetic and m-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethyldioxirane.
  • MCPBA peroxy acids
  • alkyl hydroperoxides such as t-butyl hydroperoxide
  • sodium perborate sodium perborate
  • dioxiranes such as dimethyldioxirane
  • salts of chemical compounds are in equilibrium with their corresponding nonsalt forms, salts share the biological utility of the nonsalt forms.
  • salts of the compounds of Formula 1 and Formula 2 are useful for control of undesired vegetation (i.e. are agriculturally suitable).
  • the salts of the compounds in the mixtures of this invention including Formula 1 and Formula 2 include acid-addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids.
  • inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids.
  • salts also include those formed with organic or inorganic bases such as pyridine, triethylamine or ammonia, or amides, hydrides, hydroxides or carbonates of sodium, potassium, lithium, calcium, magnesium or barium.
  • organic or inorganic bases such as pyridine, triethylamine or ammonia, or amides, hydrides, hydroxides or carbonates of sodium, potassium, lithium, calcium, magnesium or barium.
  • the salt cation is derived from the base.
  • salt cations derived from the aforementioned bases are respectively: pyridinium (C 5 HgN*), triethylammonium (HN ⁇ (Et) 3 ), ammonium (H 4 N ⁇ ), sodium (Na ⁇ ), potassium (K ⁇ ), lithium (Li ⁇ ), calcium (Ca 2 ⁇ ), magnesium (Mg 2 ⁇ ) and barium (Ba 2 ⁇ ).
  • the present invention compromises compounds selected from Formula 1, TV-oxides and agriculturally suitable salts thereof and compounds selected from Formula 2, TV-oxides and agriculturally suitable salts thereof.
  • Embodiments of the present invention include: Embodiment Al.
  • a mixture as described in the Summary of the Invention comprising a herbicidal compound of Formula 1 wherein R 2 is H, salt cation, CJ-CJ Q alkyl, C2-C 1 0 alkoxyalkyl, C 3 -C 10 alkoxyalkoxyalkyl, C2-C 1 0 hydroxyalkyl or benzyl.
  • Embodiment A2 The mixture of Embodiment Al wherein R 2 is H, salt cation, Cj- C4 alkyl, C 2 -C4 alkoxyalkyl, C 3 -C 4 alkoxyalkoxyalkyl, C 2 -C 4 hydroxyalkyl or benzyl.
  • Embodiment A3. The mixture of Embodiment A2 wherein R 2 is H, salt cation or C 1 -
  • Embodiment A4 The mixture of Embodiment Al wherein R 2 is C 5 -C 1 O alkyl C 5 -C 10 alkoxyalkyl, C 5 -C j0 alkoxyalkoxyalkyl or C 5 -C j0 hydroxyalkyl.
  • Embodiment A5 The mixture of Embodiment A4 wherein R 2 is C 5 -Cg alkyl, C 5 -Cg alkoxyalkyl or C 5 -Cg alkoxyalkoxyalkyl.
  • Embodiment A6 A mixture as described in the Summary of the Invention comprising a herbicidal compound of Formula 1 wherein R 1 is cyclopropyl.
  • Embodiment A7 A mixture as described in the Summary of the Invention comprising a herbicidal compound of Formula 1 wherein X is Cl.
  • Embodiment A8 A mixture as described in the Summary of the Invention comprising a herbicidal compound of Formula 1 wherein X is Br.
  • Embodiment Bl A mixture as described in the Summary of the Invention comprising 3 -(((5 -(difluoromethoxy)- 1 -methyl-3 -(trifluoromethyl)- lH-pyrazol-4- yl)methyl)sulfonyl)-4,5-dihydro-5,5-dimethylisoxazole (pyroxasulfone, Compound 27, Formula 2 wherein R 3 is CH 3 , R 4 is H, W is O and G is 5-
  • component (a) is selected from the group consisting of
  • 6-amino-5-chloro-2-cyclopropyl-4-pyrrmidinecarboxylic acid Compound 1
  • methyl 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylate Compound 2
  • ethyl 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylate Compound 3
  • 6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylic acid Compound 4
  • methyl 6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylate Compound 5
  • ethyl 6-ammo-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylate Compound 6
  • 6-ammo-5-chloro-2-(4-cMorophenyl)-4-pyrimidinecarboxylic acid Compound 7
  • herbicidal compositions of the present invention comprising the mixtures of embodiments described above.
  • Compounds of the invention are particularly useful for selective control of weeds in corn, wheat, barley, pasture, rangeland, sugarcane, plantation crops and also for total vegetation management.
  • This invention also relates to a method for controlling undesired vegetation comprising applying to the locus of the vegetation herbicidally effective amounts of the mixtures of the invention (e.g., as a composition described herein).
  • embodiments relating to methods of use are those involving the mixtures of embodiments described above.
  • Compounds of Formula 1 can be prepared by one or more of the methods and variations thereof as described in PCT Patent Publication WO 2005/063721, which is hereby incorporated by reference in its entirety.
  • compounds 1, 2, 5, 6, 7 and 9 as identified in Table A can be prepared by the method described in Example 2 (page 29), Example 3 (page 31), Example 1 (page 27), Example 1 (page 27), Example 4 (page 32), and Example 5 (page 33) of WO 2005/063721 respectively.
  • Tables A and B which exemplify compounds of Formula 1 in the present mixtures, can be prepared.
  • the following abbreviations are used in the Tables A-C which follow: t means tertiary, / means iso, Me means methyl, Et means ethyl, Pr means propyl (i.e. n-propyl), /-Pr means isopropyl, Bu means butyl (i.e. w-butyl), *-Bu means tert-butyl, " ⁇ " means negative formal charge, and " ® " means positive formal charge.
  • the compound numbers of Tables A, B and C refer to compounds listed as Embodiments or Specific Embodiments in the Details of the Invention. TABLE A
  • Mixtures of this invention will generally be used as a formulation or composition with an agriculturally suitable carrier comprising at least one of a liquid diluent, a solid diluent or a surfactant.
  • the formulation or composition ingredients are selected to be consistent with the_ physical. properties_of _the_ active, ingredient, mode of application and environmental factors such as soil type, moisture and temperature.
  • Useful formulations include liquids such as solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and/or suspoemulsions) and the like which optionally can be thickened into gels.
  • Useful formulations further include solids such as dusts, powders, granules, pellets, tablets, films (including seed coatings), and the like which can be water-dispersible ("wettable") or water-soluble.
  • Active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or "overcoated”). Encapsulation can control or delay release of the active ingredient.
  • Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare. High-strength compositions are primarily used as intermediates for further formulation.
  • the formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up to 100 percent by weight.
  • Typical solid diluents are described in Watkins, et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon 's Detergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, New Jersey, as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964, list surfactants and recommended uses.
  • All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth and the like, or thickeners to increase viscosity.
  • Surfactants include, for example, polyethoxylated alcohols, polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acid esters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzene sulfonates, organosilicones, NJV-dialkyltaurates, lignin sulfonates, naphthalene sulfonate formaldehyde condensates, polycarboxylates, glycerol esters, poly- oxyetKylelie/polybxyplOpylene block " c ⁇ pl)ly ⁇ r ⁇ ers7 and ⁇ alkylpolyglycosides " " where "" the ⁇ number of glucose units, referred to as degree of
  • Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate.
  • Liquid diluents include, for example, water, N//-dimethylformamide, dimethyl sulfoxide, 7V-alkylpyrrolidone, ethylene glycol, polypropylene glycol, propylene carbonate, dibasic esters, paraffins, alkylbenzenes, alkylnaphthalenes, glycerine, triacetine, oils of olive, castor, linseed, tung, sesame, corn, peanut, cotton-seed, soybean, rape-seed and coconut, fatty acid esters, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, acetates such as hexyl acetate, heptyl acetate and octyl acetate, and alcohols such as methanol, cyclohexanol, decanol, benzyl and tetrahydrofurfury
  • Useful formulations of this invention may also contain materials well known to those skilled in the art as formulation aids such as antifoams, film formers and dyes.
  • Antifoams can include water dispersible liquids comprising polyorganosiloxanes like Rhodorsil® 416.
  • the film formers can include polyvinyl acetates, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinyl acetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers and waxes.
  • Dyes can include water dispersible liquid colorant compositions like Pro-lzed® Colorant Red.
  • formulation aids include those listed herein and those listed in McCutcheon 's 2001, Volume 2: Functional Materials published by MC Publishing Company and PCT Publication WO 03/024222.
  • Solutions can be prepared by simply mixing the ingredients. Dusts and powders can be prepared by blending and, usually, grinding as in a hammer mill or fluid-energy mill. Suspensions are usually prepared by wet-milling; see, for example, U.S. 3,060,084. Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, December 4, 1967, pp 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and following, and WO 91/13546. Pellets can be prepared as described Ln U.S. 4,172,714.
  • Water-dispersible and water-soluble granules can be prepared as taught in U.S. 4,144,050,
  • Compound 2 48.5%
  • Compound 27 (pyroxasulfone) 12.5% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0% calcium/magnesium bentonite 59.0%.
  • mixtures of this invention by virtue of selective metabolism in crops versus weeds, or by selective activity at the locus of physiological inhibition in crops and weeds, or by selective placement on or within the environment of a mixture of crops and weeds, are useful for the selective control of grass and broadleaf weeds within a crop/weed mixture.
  • selectivity factors within mixtures can readily be determined by performing routine biological and/or biochemical assays.
  • Mixtures of this invention may show tolerance to important agronomic crops including, but not limited to, alfalfa, barley, cotton, wheat, rape, sugar beets, corn (maize), sorghum, soybeans, rice, oats, peanuts, vegetables, tomato, potato, perennial plantation crops including coffee, cocoa7 ⁇ oirp ⁇ alm, fubT>er7 sugarcar ⁇ e7 citrusV gfapesT fruit " trees, nut ⁇ tfees7 ⁇ banana7 plantain; pineapple, hops, tea and forests such as eucalyptus and conifers (e.g., loblolly pine), and turf species (e.g., Kentucky bluegrass, St.
  • important agronomic crops including, but not limited to, alfalfa, barley, cotton, wheat, rape, sugar beets, corn (maize), sorghum, soybeans, rice, oats, peanuts, vegetables, tomato, potato
  • Mixtures of this invention can be used in crops genetically transformed or bred to incorporate resistance to herbicides, express proteins toxic to invertebrate pests (such as Bacillus thuringiensis toxin), and/or express other useful traits. Those skilled in the art will appreciate that not all mixtures are equally effective against all weeds. Alternatively, the subject mixtures are useful to modify plant growth.
  • the mixtures of the invention have preemergent and/or postemergent herbicidal activity, to control undesired vegetation by killing or injuring the vegetation or reducing its growth
  • the mixtures can be usefully applied by a variety of methods involving contacting a herbicidally effective amount of a mixture of the invention, or a composition comprising said mixture and at least one of a surfactant, a solid diluent or a liquid diluent, to the foliage or other part of the undesired vegetation or to the environment of the undesired vegetation such as the soil or water in which the undesired vegetation is growing or which surrounds the seed or other propagule of the undesired vegetation.
  • a herbicidally effective amount of the mixtures of this invention is determined by a number of factors. These factors include: formulation selected, method of application, amount and type of vegetation present, growing conditions, etc. In general, a herbicidally effective amount of mixtures of this invention is about 0.001 to 20 kg/ha with a preferred range of about 0.004 to 7 kg/ha. One skilled in the art can easily determine the herbicidally effective amount necessary for the desired level of weed control.
  • the weight ratios of component (a) (e.g., methyl 6-amino-5-chloro-2-cyclopropyl-4- pyrimidinecarboxylate, Compound 2) and component (b) (e.g., pyroxasulfone, Compound 27) of this invention typically are between about 500:1 and about 1:500, preferably between about 200:1 and about 1:500, more preferably between about 5:1 and about 1:50, and most preferably between about 1 : 1 and about 1 :20.
  • Specifically preferred mixtures are selected from the group: compound 1 and pyroxasulfone (compound 27); compound 2 and pyroxasulfone (compound 27); compound 3 and pyroxasulfone (compound 27); compound 4 and pyroxasulfone (compound 27); compound 5 and pyroxasulfone (compound 27); compound 6 and pyroxasulfone (compound 27); compound 7 and pyroxasulfone (compound 27); compound 8 and pyroxasulfone (compound 27); compound 9 and pyroxasulfone (compound 27); compound 10 and pyroxasulfone (compound 27); compound 11 and pyroxasulfone (compound 27); compound 12 and pyroxasulfone (compound 27); compound 13 and pyroxasulfone (compound 27); compound 14 and pyroxasulfone
  • compositions which in addition to component (a) and component (b) include (c) at least one compound selected from the group consisting of: (cl) ACCase (acetyl-coenzyme A carboxylase) inhibitors; (c2) AHAS (acetohydroxy acid synthase) inhibitors; (c3) photosystem II inhibitors; (c4) photosystem I electron diverters; (c5) PPO (protoporphyrinogen oxidase) inhibitors; (c6) EPSP (5-enol- pyruvylshikimate-3 -phosphate) synthase inhibitors; (c7) GS (glutamine synthetase) inhibitors; (c8) VLCFA (very long chain fatty acid) elongase inhibitors; (c9) auxin mimics; (clO) auxin transport inhibitors; (el l) other herbicides selected from the group consisting of fiamprop-M-methyl, flamprop-M-isopropyl, d
  • Alcohol-coenzyme A carboxylase (ACCase) inhibitors (cl) are chemical compounds that inhibit the acetyl-CoA carboxylase enzyme, which is responsible for catalyzing an early step in lipids and fatty acid synthesis in plants. Lipids are essential components of cell
  • ACCase inhibitors include compounds such as clodinafop, cyhalofop, diclofop, fenoxaprop, fluazifop, haloxyfop, propaquizafop, quizalofop, alloxydim, butroxydim, clethodim, cycloxydim, profoxydim, sethoxydim, tepraloxydim and tralkoxydim, including resolved forms such as fenoxaprop-P, fluazifop-P, haloxyfop-P and quizalofop-P and ester forms such as clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl and fenoxaprop-P-ethyl.
  • AHAS inhibitors are chemical compounds that inhibit acetohydroxy acid synthase (AHAS), also known as acetolactate synthase (ALS), and th ⁇ kill " plants " by ihhib “ iting " the ⁇ productionTof the bTanch ⁇ Min ⁇ aliphatic " amino acids such " as valine, leucine and isoleucine, which are required for protein synthesis and cell growth.
  • AHAS acetohydroxy acid synthase
  • ALS acetolactate synthase
  • AHAS inhibitors include compounds such as amidosulfuron, azimsulfuron, bensulfuron- methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron- methyl, ethoxysulfuron, flazasulfuron, flupyrsulfuron-methyl (including sodium salt), foramsulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron-methyl (including sodium salt), mesosulfuron-methyl, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron- methyl, prosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron-methyl, triasulfuron, triben
  • Photosystem II inhibitors (c3) are chemical compounds that bind to the D-I protein at the QB -binding niche and thus block electron transport from Q A to Qg in the chloroplast thylakoid membranes. The electrons blocked from passing through photosystem II are transferred through a series of reactions to form toxic compounds that disrupt cell membranes and cause chloroplast swelling, membrane leakage, and ultimately cellular destruction.
  • binding site A binds the triazines such as atrazine, triazinones such as hexazinone, and uracils such as bromacil
  • binding site B binds the phenylureas such as diuron
  • binding site C binds benzothiadiazoles such as bentazon, nitriles such as bromoxynil and phenyl-pyridazines such as pyridate.
  • photosystem II inhibitors include compounds such as ametryn, cyanazine, desmetryne, dimethametryn, prometon, prometryne, propazine, simazine, simetryn, terbumeton, terbuthylazine, terbutryne, trietazine, metamitron, metribuzin, amicarbazone, lenacil, terbacil, chloridazon, desmedipham, phenmedipham, chlorobromuron, chlorotoluron, chloroxuron, " dimefuron, ethidimuron, fenuron, fluometuron, isoproturon, isouron, linuron, methabenzthiazuron, metobromuron, metoxuron, monolinuron, neburon, siduron, tebuthiuron, propanil, pentanochlor, bromofenoxim, ioxynil and pyridaf
  • Photosystem I electron diverters are chemical compounds that accept electrons from Photosystem I, and after several cycles, generate hydroxyl radicals. These radicals are extremely reactive and readily destroy unsaturated lipids, including membrane fatty acids and chlorophyll. This destroys cell membrane integrity, so that cells arid organelles "leak", leading to rapid leaf wilting and desiccation, and eventually to plant death. Paraquat and diquat are examples of this second type of photosynthesis inhibitor.
  • PPO protoporphyrinogen oxidase
  • c5 “Protoporphyrinogen oxidase (PPO) inhibitors (c5)” are chemical compounds that inhibit the enzyme protoporphyrinogen oxidase, quickly resulting in formation of highly reactive compounds " m ⁇ lants that rupture cell membranes, causing ⁇ cell " fluids " to leak ⁇ out.
  • PPO inhibitors include compounds such as acifluorfen-sodium, bifenox, chlomethoxyfen, fluoroglycofen-ethyl, fomesafen, halosafen, lactofen, oxyfluorfen, fluazolate, pyrafiufen- ethyl, cinidon-ethyl, flumioxazin, flumiclorac-pentyl, fluthiacet-methyl, thidiazimin, oxadiazon, oxadiargyl, azafenidin, carfentrazone-ethyl, sulfentrazone, pentoxazone, benzfendizone, butafenacil, pyraclonil, profluazol and flufenpyr-ethyl.
  • EPSP inhibitor herbicides are absorbed through plant foliage and translocated in the phloem to the growing points. Glyphosate is a relatively nonselective postemergence herbicide that belongs to this group.
  • Glyphosate includes its salts such as ammonium, isopropylammonium, potassium, sodium (including sesquisodium) and trimesium (alternatively named sulfosate).
  • EPSP synthase inhibitors also include compounds such as sulfosate.
  • Glutamine synthetase (GS) inhibitors (c7) are chemical compounds that inhibit the activity of the glutamine synthetase enzyme, which plants use to convert ammonia into glutamine. Consequently, ammonia accumulates and glutamine levels decrease. Plant damage probably occurs due to the combined effects of ammonia toxicity and deficiency of amino acids required for other metabolic processes.
  • the GS inhibitor glufosinate is a broad- spectrum postemergence herbicide that has no soil activity. GS inhibitors include compounds such as glufosinate, glufosinate-ammonium and bilanaphos.
  • Elongase is one of the enzymes located in or near chloroplasts which are involved in biosynthesis of very-long-chain fatty acids (VLCFAs).
  • VLCFAs very-long-chain fatty acids
  • very-long-chain fatty acids are the main constituents of hydrophobic polymers that prevent desiccation at the leaf surface and provide stability to pollen grains.
  • VLCFA Very long chain fatty acid
  • elongase inhibitors include herbicides having a wide variety of chemical structures, such as acetochlor, alachlor, butachlor, dimethachlor, dimethanamid, metazachlor, metolachlor, pethoxamid, pretilachlor, propachlor, propisochlor, thenylchlor, diphenamid, napropamide, naproanilide, flufenacet, indanofan, mefenacet, fentrazamide, anilofos, cafenstrole and piperophos, including resolved forms such as S-metolachlor.
  • Auxin is a plant hormone that regulates growth in many plant tissues.
  • “Auxin mimics (c9)” are chemical compounds mimicking the plant growth hormone auxin, thus causing uncontrolled and disorganized growth leading to plant death in susceptible species.
  • Auxin mimics include compounds such as clomeprop, 2,4-D, 2,4-DB, dichlorprop, MCPA, MCPB, mecoprop, chloramben, dicamba, TBA, clopyralid, fluroxypyr, picloram, triclopyr, quinclorac, quinmerac and benazolin-ethyl.
  • auxin transport inhibitors are chemical substances that inhibit auxin transport in plants, such as by binding with an auxin-carrier protein.
  • auxin transport inhibitors include naptalam (also known as N-(l-naphthyl)phthalamic acid and 2-[(l- naphthalenylamino)carbonyl]benzoic acid) and diflufenzopyr.
  • component (a) e.g., methyl 6-amino-5-chloro-2- cyclopropyl-4-pyrimidinecarboxylate, Compound 2) and component (b) (e.g., pyroxasulfone, Compound 27) with component (c) selected from rimsulfuron, nicosulfuron, thifensulfuron- methyl, tribenuron-methyl, chlorimuron-ethyl, metsulfuron-methyl, chlorsulfuron, sulfometuron-methyl, bensulfuron-methyl, pyrithiobac-sodium, atrazine, bentazon, bromoxynil, mesotrione, topramezone, tembotrione, isoxaflutole, imazethapyr, imazapyr, imazaquin, fiumetsulam, cloransulam-methyl, foramsulfuron, iodosulfur
  • component (a) e.g., methyl 6-amino-5-chloro-2-cyclopropyl-4- pyrimidinecarboxylate, Compound 2) and component (b) (e.g., pyroxasulfone, Compound 27) with component (c) selected from the group consisting of rimsulfuron, nicosulfuron, thifensulfuron-methyl, tribenuron-methyl, chlorimuron-ethyl, metsulfuron-methyl, atrazine, mesotrione, topramezone, tembotrione, isoxaflutole, imazapyr, fiumetsulam, cloransulam- methyl, foramsulfuron, iodosulfuron-methyl (including sodium salt), halosulfuron-methyl, quizalofop, clethodim, sethoxydim, carfentrazone-e
  • component (c) selected from the group consisting of rimsul
  • Mixtures of this invention can be mixed with one or more insecticides, fungicides, nematocides, bactericides, acaricides, growth regulators, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants or other biologically active compounds to form a multi-component pesticide giving an even broader spectrum of agricultural protection.
  • insecticides such as abamectin, acephate, azinphos-methyl, bifenthrin, buprofezin, carbofuran, chlorfenapyr, chlorantraniliprole, chlorpyrifos, chlorpyrifos-methyl, cyflumetofen, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhaldthrin, deltamethrin, diafe ⁇ thiur ⁇ h " , diazin ⁇ n, difl ⁇ be ⁇ zur ⁇ n, dimefluthrin, dimethoate, dinotefuran, esfenvalerate, fenoxycarb, fenpropathrin, fen valerate, fipronil, flonicamid, flubendiamide, flucythrinate, tau-fluvalinate, fono
  • Mixtures of this invention can also be used in combination with herbicide safeners such as benoxacor, BCS (l-bromo-4-[(chloromethyl)sulfonyl]benzene), cloquintocet-mexyl, cyometrinil, dichlormid, 2-(dichloromethyl)-2-methyl-l,3-dioxolane (MG 191), fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr- ethyl, methoxyphenone ((4-methoxy-3-methylphenyl)(3-methylphenyl)methanone), naphthalic anhydride (1,8-naphthalic anhydride) and oxabetrinil to increase safety to certain crops.
  • herbicide safeners such as benoxacor, BCS (l-bromo-4-[(
  • Antidotally effective amounts of the herbicide safeners can be applied at the same time as the mixtures of this invention, or applied as seed treatments. Therefore an aspect of the present invention relates to a herbicidal mixture comprising a mixture of this invention and an antidotally effective amount of a herbicide safener. Seed treatment is particularly useful for selective weed control, because it physically restricts antidoting to the crop plants. Therefore a particularly useful embodiment of the present invention is a method for selectively controlling the growth of undesired vegetation in a crop comprising contacting the locus of the crop with a herbicidally effective amount of a mixture of this invention wherein seed from which the crop is grown is treated with an antidotally effective amount of safener.
  • Antidotally effective amounts of safeners can be easily determined by one skilled in the art through simple experimentation.
  • Mixtures of this invention can also be used in combination with plant growth regulators such as aviglycine, 7V-(phenyknethyl)-lH-purin-6-amine, epocholeone, gibberellic acid, gibberellin A 4 and A 7 , harpin protein, mepiquat chloride, prohexadione calcium, prohydrojasmon, sodium nitrophenolate and trinexapac-methyl, and plant growth modifying organisms such as Bacillus cereus strain BPOl.
  • Mixtures of this invention typically provide a broader spectrum of control of undesired vegetation than provided by each active herbicide ingredient separately.
  • mixtures of herbicides having a similar spectrum of control but different sites of action can be particularly advantageous in certain situations for preventing the development of resistant weed populations.
  • many of the mixtures of this invention have been discovered to provide a greater-than-additive (i.e. synergistic) effect on weeds and/or a less-than-additive (i.e. safening) effect on crops or other desirable plants compared to the control expected based on the effects of the individual components.
  • Herbicidally effective amounts of the herbicidal active ingredients in the mixtures of this invention including amounts to achieve synergism (i.e. synergistically effective amounts) or safening (i.e. safening effective amounts), to achieve the desired spectrum of weed control and safety to desired vegetation can be easily determined by one skilled in the art through simple experimentation.
  • Tests demonstrate the control efficacy of the mixtures of this invention against specific weeds and/or on crops including other desirable plants.
  • the control afforded by the mixtures are not limited, however, to these species.
  • P a+b P a + P b - (P a P b / 100) wherein P a+b is the percentage effect of the mixture expected from additive contribution of the individual components, P a is the observed percentage effect of the first active ingredient at the same use rate as in the mixture, and
  • P b is the observed percentage effect of the second active ingredient at the same use rate as in the mixture.

Abstract

L'invention concerne un mélange herbicide comprenant : (a) au moins un composé herbicide sélectionné parmi les pyrimidines de formule (I), des N-oxydes et des sels de celles-ci : (I) (dans laquelle R1 est un groupe cyclopropyle, 4-Br-phényle ou 4-Cl-phényle; X est Cl ou Br; R2 est H, un alkyle en C1-C14, un alcoxyalkyle en C2-C14, un alcoxyalcoxyalkyle en C3-C14, un hydroxyalkyle en C2-C14 ou un benzyle); et (b) au moins un composé herbicide supplémentaire sélectionné parmi les composés de formule (II), des N-oxydes et des sels de ceux-ci : (II) (dans laquelle R3, R4, W et G sont tels que définis dans la description). L'invention concerne également un procédé servant à lutter contre le développement d'une végétation non souhaitée consistant à mettre en contact la végétation ou son environnement avec une quantité efficace du point de vue herbicide d'une composition comprenant un mélange de l'invention et comprenant éventuellement en plus au moins un autre herbicide.
PCT/US2007/025224 2006-12-12 2007-12-10 Mélanges herbicides WO2008073369A1 (fr)

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009029750A2 (fr) * 2007-08-30 2009-03-05 E. I. Du Pont De Nemours And Company Compositions herbicides granulaires sans danger pour le gazon
JP2014505072A (ja) * 2011-01-25 2014-02-27 ダウ アグロサイエンシィズ エルエルシー ４−アミノ−６−（置換フェニル）ピコリネートおよび６−アミノ−２−（置換フェニル）−４−ピリミジンカルボキシレートのアリールアルキルエステルならびに除草剤としてのそれらの使用
CN104186477A (zh) * 2014-09-11 2014-12-10 河南远见农业科技有限公司 一种棉花田土壤处理除草剂组合物及应用
CN105594711A (zh) * 2015-12-21 2016-05-25 南京华洲药业有限公司 一种包括苯唑草酮与西玛津的混合除草剂及其应用
WO2021093592A1 (fr) * 2019-11-12 2021-05-20 江苏清原农冠杂草防治有限公司 Composition herbicide comprenant un composé de benzyl pyrimidine carboxylate et son application

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WO2005063721A1 (fr) * 2003-12-19 2005-07-14 E.I. Dupont De Nemours And Company Pyrimidines herbicides
US20050256004A1 (en) * 2002-08-07 2005-11-17 Satoru Takahashi Herbicide compositions

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Publication number Priority date Publication date Assignee Title
US20050256004A1 (en) * 2002-08-07 2005-11-17 Satoru Takahashi Herbicide compositions
WO2005063721A1 (fr) * 2003-12-19 2005-07-14 E.I. Dupont De Nemours And Company Pyrimidines herbicides

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009029750A2 (fr) * 2007-08-30 2009-03-05 E. I. Du Pont De Nemours And Company Compositions herbicides granulaires sans danger pour le gazon
WO2009029750A3 (fr) * 2007-08-30 2009-08-06 Du Pont Compositions herbicides granulaires sans danger pour le gazon
JP2014505072A (ja) * 2011-01-25 2014-02-27 ダウ アグロサイエンシィズ エルエルシー ４−アミノ−６−（置換フェニル）ピコリネートおよび６−アミノ−２−（置換フェニル）−４−ピリミジンカルボキシレートのアリールアルキルエステルならびに除草剤としてのそれらの使用
RU2566760C2 (ru) * 2011-01-25 2015-10-27 ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи Сложные арилалкиловые эфиры 4-амино-6-(замещенный фенил)пиколинатов и 6-амино-2-(замещенный фенил)-4-пиримидинкарбоксилатов и их применение в качестве гербицидов
JP2016074722A (ja) * 2011-01-25 2016-05-12 ダウ アグロサイエンシィズ エルエルシー ４−アミノ−６−（置換フェニル）ピコリネートおよび６−アミノ−２−（置換フェニル）−４−ピリミジンカルボキシレートのアリールアルキルエステルならびに除草剤としてのそれらの使用
CN104186477A (zh) * 2014-09-11 2014-12-10 河南远见农业科技有限公司 一种棉花田土壤处理除草剂组合物及应用
CN105594711A (zh) * 2015-12-21 2016-05-25 南京华洲药业有限公司 一种包括苯唑草酮与西玛津的混合除草剂及其应用
WO2021093592A1 (fr) * 2019-11-12 2021-05-20 江苏清原农冠杂草防治有限公司 Composition herbicide comprenant un composé de benzyl pyrimidine carboxylate et son application
CN112841195A (zh) * 2019-11-12 2021-05-28 江苏清原农冠杂草防治有限公司 包含嘧啶羧酸苄酯类化合物的除草组合物及其应用
CN112841195B (zh) * 2019-11-12 2021-11-05 江苏清原农冠杂草防治有限公司 包含嘧啶羧酸苄酯类化合物的除草组合物及其应用

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