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WO1991013548A1 - Compositions herbicides de 1,3-dicarbonyle ou de 1,3,5-tricarbonyle cyclohexane aroyles et systeme d'antidote relatif a ces compositions - Google Patents

Compositions herbicides de 1,3-dicarbonyle ou de 1,3,5-tricarbonyle cyclohexane aroyles et systeme d'antidote relatif a ces compositions Download PDF

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Publication number
WO1991013548A1
WO1991013548A1 PCT/US1991/001709 US9101709W WO9113548A1 WO 1991013548 A1 WO1991013548 A1 WO 1991013548A1 US 9101709 W US9101709 W US 9101709W WO 9113548 A1 WO9113548 A1 WO 9113548A1
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WO
WIPO (PCT)
Prior art keywords
alkyl
hydrogen
cyano
alkoxy
halogen
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PCT/US1991/001709
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English (en)
Inventor
James L. Ahle
Ferenc M. Pallos
Original Assignee
Ahle James L
Pallos Ferenc M
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 Ahle James L, Pallos Ferenc M filed Critical Ahle James L
Publication of WO1991013548A1 publication Critical patent/WO1991013548A1/fr

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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
    • A01N35/06—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 containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
    • 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
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/10—Sulfones; Sulfoxides

Definitions

  • a beneficial crop is susceptible to the effects of the herbicide.
  • certain herbicidal compounds are phytotoxic to some weed species but not to others.
  • an herbicide must cause minimal damage (preferably no damage) to the beneficial crop while maximizing damage to weed species which infest the locus of the crop.
  • R 1 is hydrogen or C 1 -C 4 alkyl
  • R 2 is hydrogen or C 1 -C 4 alkyl
  • R 1 and R 2 together are C 2 -C 5 alkylene
  • R 4 is C 1 -C 4 alkyl
  • R 3 and R 4 together are C 2 -C 5 alkylene
  • R 5 and R 6 independently are (1) hydrogen; (2) halogen; (3) C 1 -C 4 thioalkyl; (4) C 1 -C 4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C 1 -C 4 haloalkyl;
  • C 1 -C 4 alkyl includes methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl and t- butyl.
  • halogen includes chlorine, bromine, iodine and fluorine.
  • C 1 -C 4 alkoxy includes methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec- butoxy, isobutoxy and t-butoxy.
  • C 1 -C 4 haloalkyl includes the alkyl groups defined above under C 1 -C 4 alkyl in which one or more hydrogen is replaced by chlorine, bromine, iodine or fluorine.
  • the tricarbonylcyclohexane herbicide compounds of this invention and their salts are active herbicides of a general type. That is, they are herbicidally effective against a wide range of plant species.
  • the method of controlling undesirable vegetation of the present invention comprises applying an herbicidally effective amount of the above-described compounds or their salts to the area where control is desired.
  • R is an optionally substituted aromatic moiety as hereinafter defined and n is 2 or 3, preferably 3.
  • the ring can be saturated (all X and Y groups are hydrogen), or one or more hydrogen atoms may be replaced by aliphatic, aromatic, heterocyclic or alkylene groups, particularly hydrocarbyl groups. Examples of such hydrocarbyl groups are alkyl, particularly lower alkyl, phenyl, and C 2 -C 5 alkylene groups such as dimethylene, trimethylene and the like, in which case the compounds have a spiro structure.
  • the carbocyclic ring may be saturated or unsaturated, containing an olefinic bond linking the 4- and 5-carbon atoms.
  • R 1 or R 3 is R a OC- in which
  • R a is C 1 -C 4 alkyl; phenyl, optionally substituted by from 2 to 5 methyl groups; or R 3 is hydroxyl and R 1 ,
  • R 2 , R 4 , R 5 and R 6 are independently hydrogen or C 1 -C 4 alkyl; or in which R 1 and R 2 , or R 3 and R 4 , taken together are C 2 -C 5 alkylene (such compounds have a spiro structure;
  • R 8 , R 9 and R 10 independently are hydrogen or substituents including halogen; C 1 -C 4 alkyl; C 1 -C 4 alkoxy, trifluoromethoxy; cyano; nitro; C 1 -C 4 haloalkyl; C 1 -C 4 alkylthio; phenoxy; or substituted phenoxy in which the substituent is halogen or halomethyl or both;
  • R b S(O) n in which n is 0, 1 or 2; and R b is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, phenyl or benzyl,
  • R C CNH- in which R c is C 1 -C 4 alkyl
  • R d and R e independently are hydrogen or C 1 -C 4 alkyl
  • R f C(O)- in which R f is hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 alkoxy;
  • R 8 and R 9 taken together form a ring structure with two adjacent carbon atoms of the phenyl ring to which they are attached.
  • Some specific types of such aroylated heterocyclic 1,3-dicarbonyl herbicide compounds include:
  • barbituric acid derivatives such as those of the formula
  • R 18 and R 19 are hydrogen or C 1 -C 4 alkyl and R is substituted phenyl such as
  • R 15 , R 16 and R 17 are as defined hereinafter.
  • Such compounds are described, for instance, in commonly assigned U.S. Patent 4,797,147, issued January 10, 1989, the disclosure of which is hereby incorporated herein by reference;
  • R 11 -R 14 and R 20 are independently hydrogen or C 1 -C 4 alkyl, or R 11 and R 12 together are C 2 -C 5 alkylene, t is 0 or
  • R is substituted phenyl such as
  • R 15 is halogen; C 1 -C 2 alkyl; C 1 -C 2 alkoxy; nitro; cyano; C 1 -C 2 haloalkyl; or R m SO n wherein R m is C 1 -C 2 alkyl and n is 0, 1 or 2; trifluoromethyl or difluoromethyl; or t ⁇ fluoromethoxy or difluoromethoxy.
  • R 15 is chlorine, bromine, C 1 -C 2 alkyl, C 1 -C 2 alkoxy, trifluoromethyl, cyano, nitro, C 1 -C 2 alkylthio or C 1 -C 2 alkylsulfonyl; and R 1 6 and R 1 7 independently are (1) hydrogen, (2) halogen,
  • herbicidal oxolactones and oxothiolactones within this invention such as those having the formula
  • R 21 -R 24 are independently hydrogen or C 1 -C 4 alkyl; or R 21 and R 22 together are C 2 -C 5 alkylene; or R 23 and R 24 together are C 2 -C 5 alkyl; or R 21 and R 23 together form a bond, and R is substituted phenyl such as
  • R 15 -R 17 are as defined above; and W is oxygen or sulfur.
  • R 21 and R 23 together form a bond the compounds contain an unsaturated heterocyclic ring.
  • Such compounds are disclosed, for instance, in commonly assigned U.S. Pat.
  • dioxotetrahydropyrans and -thiopyrans such as those having the formula
  • R 2 6 -R 2 9 are independently hydrogen or C 1 -C 4 alkyl or
  • R 26 and R 27 together are C 2 -C 5 alkylene, or R 28 and R 29 together are C 2 -C 5 alkylene;
  • W 2 is oxygen, sulfur or sulfonyl and
  • R 30 is substituted phenyl such as
  • R 15 -R 17 are as previously defined.
  • Such compounds are described, for instance, in commonly assigned U.S. Pat.
  • Another embodiment of this invention is an herbicidal composition
  • the 1,3-cyclohex- anedione moiety is preferably substituted with groups hereinafter defined.
  • the benzoyl and cyclohexanedione moieties can be further substituted.
  • R in Formula C above is a substituted phenyl. In general, these compounds have the formula
  • R 130 is halogen; C 1 -C 2 alkyl; C 1 -C 2 alkoxy; trifluoromethoxy or difluoromethoxy; nitro; cyano; C 1 -C 2 haloalkyl; R a SO n - wherein n is 0 or 2; and R a is C 1 -C 2 alkyl;
  • R 140 is chlorine, bromine, C 1 -C 2 alkyl, C 1 -C 2 alkoxy, trifluoromethyl, cyano, nitro, C 1 -C 2 alkylthio or C 1 -C 2 alkylsulfonyl; more preferably chlorine, nitro, methyl, trifluoromethyl or methylsulfonyl;
  • R 131 is hydrogen or C 1 -C 4 alkyl
  • R 132 is hydrogen or C 1 -C 4 alkyl
  • R 131 and R 132 together are C 2 -C 5 alkylene;
  • R 133 is hydrogen or C 1 -C 4 alkyl;
  • R 134 is hydrogen or C 1 -C 4 alkyl
  • R 135 , R 136 , R 137 and R 138 independently are (1) hydrogen; (2) chlorine, fluorine or bromine; (3) C 1 -C 4 alkyl; (4) C 1 -C 4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C 1 -C 4 haloalkyl; (9) R b SO n - wherein n is the integer 0, 1 or 2; and
  • R 40 is halogen; C 1 -C 2 alkyl; C 1 -C 2 alkoxy; trifluoromethoxy or difluoromethoxy; nitro; cyano; C 1 -C 2 haloalkyl; R a SO n - wherein n is 0 or 2; and R a is C 1 -C 2 alkyl; trifluoromethyl; or difluoromethyl;
  • R 41 is hydrogen or C 1 -C 4 alkyl
  • R 42 is hydrogen or C 1 -C 4 alkyl
  • R 41 and R 42 together are C 2 -C 5 alkylene
  • R 43 is hydrogen or C 1 -C 4 alkyl
  • R 44 is hydrogen or C 1 -C 4 alkyl
  • R 43 and R 44 together are C 2 -C 5 alkylene
  • R 45 , R 46 , R 47 and R 48 independently are (1) hydrogen; (2) halogen selected from the group consisting of chlorine, fluorine or bromine; (3) C 1 -C 4 alkyl; (4) C 1 -C 4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C 1 -C 4 haloalkyl; (9) R b SO n - wherein n is the integer 0, 1 or 2; and
  • R b is (a) C 1 -C 4 alkyl
  • R 49 is hydrogen or C 1 -C 4 alkyl.
  • R 45 is in the 3-posit ⁇ on and R 45 is hydrogen, chlorine, fluorine, trifluoromethyl, cyano, C 1 -C 4 alkoxy or C 1 -C 4 thioalkyl; or
  • R 45 is hydrogen; or R 46 is in the 4-position and R 46 is halogen, cyano, trifluoromethyl, or R b SO 2 wherein R b is C 1 -C 4 alkyl, preferably methyl or C 1 -C 4 haloalkyl, difluoromethyl or trifluoromethyl.
  • Another embodiment of this invention is an herbicidal composition
  • the 5- and 6-positions of the 1,3-cyclo- hexanedione moiety are preferably substituted with groups hereinafter defined, most preferably with hydrogen or methyl groups.
  • the substituted benzoyl and cyclohexanedione moieties can be further substituted.
  • R 50 is halogen; C 1 -C 2 alkyl; C 1 -C 2 alkoxy, preferably methoxy; trifluoromethoxy; difluoromethoxy; nitro;
  • R 50 is chlorine, bromine, C 1 -C 2 alkyl, C 1 -C 2 alkoxy, trifluoromethyl, cyano, nitro, C 1 -C 2 alkylthio or C 1 -C 2 alkylsulfonyl; more preferably chlorine, nitro, methyl, trifluoromethyl or methylsulfonyl;
  • R 51 is hydrogen; C 1 -C 4 alkyl, phenyl or substituted phenyl;
  • R 53 is hydrogen, C 1 -C 4 alkyl, phenyl or substituted phenyl with the proviso that R 51 and R 53 are not both phenyl or substituted phenyl;
  • R 54 is hydrogen or C 1 -C 4 alkyl
  • R b is (a) C 1 -C 4 alkyl
  • Another embodiment of this invention is an herbicidal composition
  • the 5- and 6-positions of the 1,3-cyclohexanedione moiety are substituted with groups hereinafter defined, preferably with hydrogen or methyl groups.
  • the benzoyl and imino, oximino or carbonyl moieties can be substituted.
  • X is oxygen or NR 69 wherein R 69 is hydrogen, C 1 -C 4 alkyl, or C 1 -C 4 alkoxy;
  • R 60 is halogen; C 1 -C 2 alkyl; C 1 -C 2 alkoxy; trifluoromethoxy or difluoromethoxy; nitro; cyano; C 1 -C 2 haloalkyl; R a SO n - wherein n is 0 or 2, and R a is C 1 -C 2 alkyl;
  • R 60 is chlorine, bromine, C 1 -C 2 alkyl, C 1 -C 2 alkoxy, trifluoromethyl, cyano, nitro, C 1 -C 2 alkylthio or C 1 -C 2 alkylsulfonyl; more preferably chlorine, nitro, methyl, trifluoromethyl or methylsulfonyl;
  • R 61 is hydrogen; C 1 -C 4 alkyl, phenyl or substituted phenyl;
  • R 61 is hydrogen or C 1 -C 4 alkyl
  • R 63 is hydrogen, C 1 -C 4 alkyl, phenyl or substituted phenyl with the proviso that R 61 and R 63 are not both phenyl or substituted phenyl;
  • R 64 is hydrogen or C 1 -C 4 alkyl
  • R 65 is hydrogen or C 1 -C 4 alkyl
  • R 67 and R 68 independently are (1) hydrogen; (2) halogen; (3) C 1 -C 4 alkyl; (4) C 1 -C 4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C 1 -C 4 haloalkyl, preferably trifluoromethyl; (9) R b SO n - wherein n is the integer 0, 1 or 2, preferably 2; and
  • R b is (a) C 1 -C 4 alkyl
  • R 70 is halogen; C 1 -C 2 alkyl; C 1 -C 2 alkoxy, trifluoromethoxy or difluoromethoxy; nitro; cyano; C 1 -C 2 haloalkyl; R a SO n - wherein n is 0 or 2, and R a is C 1 -C 2 - alkyl; trifluoromethyl or difluoromethyl.
  • R 70 is chlorine, bromine, C 1 -C 2 alkyl, C 1 -C 2 alkoxy, trifluoromethyl, cyano, nitro, C 1 -C 2 alkylthio or C 1 -C 2 alkylsulfonyl; more preferably chlorine, nitro, methyl, trifluoromethyl or methylsulfonyl;
  • R 71 is hydrogen; C 1 -C 4 alkyl, halogen, phenyl or substituted phenyl;
  • R 71 is hydrogen or C 1 -C 4 alkyl
  • R 71 and R 72 together are C 2 -C 5 alkylene
  • R 73 is hydrogen, C 1 -C 4 alkyl, phenyl or substituted phenyl, with the proviso that R 71 and R 73 are not both phenyl or substituted phenyl;
  • R 74 is hydrogen or C 1 -C 4 alkyl
  • R 76 is halogen, nitro, cyano, trifluoromethyl
  • R b is hydrogen or C 1 -C 2 alkyl
  • R 77 and R 78 independently are (1) hydrogen; (2) halogen; (3) C 1 -C 4 alkyl; (4) C 1 -C 4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C 1 -C 4 haloalkyl; (9)
  • n is the integer 0, 1 or 2;
  • R b is (a) C 1 -C 4 alkyl
  • R 77 is in the 3-position and R 77 is hydrogen, chlorine, fluorine, trifluoromethyl, cyano, C 1 -C 4 alkoxy or C 1 -C 4 thioalkyl
  • R 78 is in the 4-position and R 78 is halogen, cyano, trifluoromethyl, or R b SO 2 wherein R b is C 1 -C 4 alkyl, or C 1 -C 4 haloalkyl, preferably chloromethyl, difluoromethyl or trifluoromethyl.
  • This invention embodies a herbicidal agent with an antidote comprised of (a) the herbicide as described herein- above and (b) effective antidotes therefor. It has been found that such antidote compounds must be selected from a specific range of chemical substances that have been found to be effective as herbicide antidotes for protection of crops from the above-described aroylated 1,3-dicarbonyl and 1,3,5- tricarbonyl cyclohexane herbicides. The effectiveness on crops on which the above-described herbicides are useful can be significantly broadened by the use of the antidote described herein to protect crops from injury therefrom and render the compositions more crop selective while controlling the weed pests.
  • Preferred types of antidotes are 1,8-naphthalic anhydride, its salts, tertiary amine salts and esters.
  • the amount of 1,8-naphthalic anhydride and 1,8- naphthalic dicarboxylic acid, derivatives thereof or salts thereof of the above-described herbicide compositions of this invention and the manner of this utilization and resulting efficacy can vary according to various parameters, such as the particular antidote employed, the crop which is protected, the amount or rate of herbicide applied, the soil and climatic conditions of the agricultural environment in which the mixture is applied.
  • the selection of specific antidotes for use in the herbicide composition, the manner in which it is applied, the determination of activity which is non-phytotoxic but antidotally effective, and the amount necessary to provide this result can be readily performed in accordance with common practice in the art.
  • Herbicide compounds and antidotes employed in the tests were sprayed in an acetone-water solution containing 0.5% polyoxyethylene sorbitan monolaurate emulsifier.
  • Herbicides and antidotes were applied as post-emergence tank mix solutions (POES) with a carrier volume of 25 gal/A. All seeds were seeded in aluminum flats (16x23x7 cm) of which holes were punched in the bottom to allow water drainage.
  • POES post-emergence tank mix solutions
  • Seeds were planted 1-3 cm deep, in a sandy loam soil fortified with fertilizer (17-17-17; Garden Valley Fertilizer Co., San Jose, CA 95112) and the fungicide Captan 80W. Approximately 14-16 days after seeding, the plants were sprayed in a linear spray table.
  • the antidotes described herein can be formulated in a number of ways for suitable application: (a) the antidotes can be formulated for application directly to the crop seed; (b) the antidotes and herbicide can be formulated separately and applied separately or applied simultaneously in an appropriate weight ratio, i.e., as a tank mix, or (c) the antidotes and herbicide may be formulated together in the proper weight ratio.
  • Useful formulations of the compounds of this invention can be prepared in conventional ways. They include dusts, granules, microcapsules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly to the locus. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation.
  • the formulations broadly, contain about 0.1% to about 99% by weight of active herbicide and antidote ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 2% to about 99.9% solid or liquid inert diluent(s). More specifically, they can contain these ingredients in the following approximate proportions.
  • Dusts are free-flowing powder compositions containing the formulant impregnated on a particulate carrier.
  • the particle size of the carriers is usually in the approximate range of 30 to 50 microns.
  • suitable carriers are talc, bentonite, diatomaceous earth, and pyrophyllite.
  • the composition generally contains up to 50% of formulant.
  • Anti-caking and anti-static agents may also be added. Dusts may be applied by spraying from boom sprayers, hand sprayers or airplanes.
  • Wettable powders are finely divided compositions comprising a particular carrier impregnated with the formulant and additionally containing one or more surface active agents.
  • the surface active agent promotes rapid dispersion of the powder in an aqueous medium to form stable, sprayable suspensions.
  • a wide variety of surface active agents can be used, for example, long chain fatty alcohols and alkali metal salts of the sulfate fatty alcohols; salts of sulfonic acid; esters of long chain fatty acids; and polyhydric alcohols, in which the alcohol groups are free, omega-substituted polyethylene glycols of relatively long chain length.
  • a list of surface active agents suitable for use in agriculture formulations can be found in Wade Van Valkenburg, Pesticide
  • Granules comprise the formulant impregnated on a particulate inert carrier having a particle size of about 1 to 2 millimeters (mm) in diameter.
  • the granules can be made by spraying a solution of the formulant in a volatile solvent onto the granular carrier.
  • suitable carriers for the preparation of granules include clay, vermiculite, sawdust and granular carbon.
  • Microcapsules and other slow release formulations are advantageous as formulations to deliver and distribute the active ingredients.
  • Microcapsules consist of fully enclosed droplets or granules containing the active materials in whidh the enclosing material is an inert porous membrane, arranged to allow escape of the enclosed materials to the surrounding medium at controlled rates over a specified period of time.
  • Encapsulated droplets are typically about 1 to 50 microns in diameter.
  • the enclosed liquid typically constitutes about 50 to 95% of the weight of the entire capsule, and may contain an amount of solvent in addition to the active materials.
  • Encapsulated granules are characterized by porous membranes sealing the openings of the granule carrier pores, trapping the liquid containing the active components inside for controlled release.
  • a typical granule size ranges from 1 mm to 1 centimeter (cm) in diameter.
  • Useful encapsulating materials include natural and synthetic rubbers, cellulosic materials, styrene-butadiene copolymers, polyacylonitriles, polyacrylates, polyesters, polyamides, polyureas, polyurethanes and starch xanthates.
  • the proportion of antidote compounds to herbicide compound generally ranges from approximately 0.001 to 30 parts by weight of the antidote compounds per weight of the herbicide compound.
  • Formulations generally contain several additives in addition to the formulant and carrier or agent.
  • inert ingredients diluent carriers, organic solvents, water, oil and water, water-in-oil emulsions, carriers of dusts and granules, and surface active wetting, dispersing and emulsifying agents.
  • Fertilizers e.g., ammonium nitrate, urea and superphosphate, may be included.
  • Aids to rooting and growth e.g., compost, manure, humus and sand, may also be included.
  • the antidote compounds and herbicide and antidote compositions of this invention can be applied to a crop by addition of the formulant to irrigation water supplied to the field to be treated. This method of application permits the penetration of the compositions into the soil as the water is absorbed.
  • the formulant can be applied to the soil in the form of a solution in a suitable solvent.
  • Solvents frequently used in these formulations include kerosene, fuel oil, xylene, petroleum fractions with boiling ranges above xylene and aromatic petroleum fractions rich in methylated naphthalenes.
  • Liquid solutions, like dusts, may be applied by spraying from boom and hand sprayers or airplanes.
  • Dusts The following substances are used to formula (a) a 5% and (b) a 2% dust:
  • the active substances are mixed with the carriers and ground, and in this form can be processed to dusts for application.
  • the active substances are intimately mixed in suitable mixers with the additives and ground in appropriate mills and rollers. Wettable powders of excellent wettability and suspension power are obtained. These wettable powders can be diluted with water to give suspensions of the desired concentration and can be used in particular for treating parts of plants.
  • Emulsifiable concentrate The following substances are used to formulate a 25% emulsifiable concentrate:

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
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Abstract

Herbicide post-germination et composition herbicide servant d'antidote comprenant: a) une quantité efficace en tant qu'herbicide d'un composé de 1,3,5-cyclohexanetrione aroylé ou d'un composé de 1,3-dicarbonyle cyclique aroylé; et, b) une quantité efficace non phytotoxique en tant qu'antidote d'un dérivé d'acide 1,8-naphtalique dicarboxylique choisi parmi le groupe composé d'anhydride 1,8-naphtalique, de dérivés d'anhydride 1,8-naphtalique, d'acide 1,8-naphtalique dicarboxylique, de dérivés d'acide 1,8-naphtalique dicarboxylique, de sels et de compositions de ces composés.
PCT/US1991/001709 1990-03-14 1991-03-13 Compositions herbicides de 1,3-dicarbonyle ou de 1,3,5-tricarbonyle cyclohexane aroyles et systeme d'antidote relatif a ces compositions WO1991013548A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US667,903 1976-03-17
US49425090A 1990-03-14 1990-03-14
US494,250 1990-03-14
US8375291P 1991-03-12 1991-03-12

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EP1836894A1 (fr) 2006-03-25 2007-09-26 Bayer CropScience GmbH Nouvelles formulations solides à base de sulfonamides
EP1844654A1 (fr) 2006-03-29 2007-10-17 Bayer CropScience GmbH Activateur de la pénétration foliaire des principes actives agrochimiques
DE102007013362A1 (de) 2007-03-16 2008-09-18 Bayer Cropscience Ag Penetrationsförderer für herbizide Wirkstoffe
WO2011076731A1 (fr) 2009-12-23 2011-06-30 Bayer Cropscience Ag Formulation liquide de 2-iodo-n-[(4-méthoxy-6-méthyl-1, 3, 5-triazin-2-yl) carbamoyl] benzène sulfonamide
WO2012110517A1 (fr) 2011-02-15 2012-08-23 Bayer Cropscience Ag Combinaisons synergiques contenant un fongicide dithiino-tétracarboxamide et un herbicide, un phytoprotecteur ou un régulateur de croissance végétale
DE102011080020A1 (de) 2011-07-28 2012-09-13 Bayer Cropscience Ag Verwendung von Saatgutbehandlungs-Wirkstoffen aus der Gruppe der Dicarboximid-Fungizide als Safener
DE102011080004A1 (de) 2011-07-28 2012-09-13 Bayer Cropscience Ag Verwendung von Saatgutbehandlungs-Wirkstoffen aus der Gruppe der Carbamat-Fungizide als Safener
DE102011079991A1 (de) 2011-07-28 2012-09-13 Bayer Crop Science Ag Verwendung von Saatgutbehandlungs-Wirkstoffen aus der Gruppe der Nicotinoid-Insektizide als Safener
DE102011079997A1 (de) 2011-07-28 2012-09-13 Bayer Corpscience Ag Verwendung von Saatgutbehandlungs-Wirkstoffen aus der Gruppe der Pyrazol-Insektizide als Safener
DE102011080007A1 (de) 2011-07-28 2012-09-13 Bayer Cropscience Ag Verwendung von Saatgutbehandlungs-Wirkstoffen aus den Gruppen der Conazole- und Triazol-Fungizide als Safener
DE102011080016A1 (de) 2011-07-28 2012-10-25 Bayer Cropscience Ag Verwendung von Saatgutbehandlungs-Wirkstoffen aus der Gruppe der Strobilurin-Fungizide als Safener
DE102011080001A1 (de) 2011-07-28 2012-10-25 Bayer Cropscience Ag Verwendung von Saatgutbehandlungs-Wirkstoffen aus der Gruppe der Carbamat-Insektizide als Safener
DE102011080010A1 (de) 2011-07-28 2012-10-25 Bayer Cropscience Ag Verwendung von Saatgutbehandlungs-Wirkstoffen aus den Gruppen der Anilid- und Thiazol-Fungizide als Safener
WO2014060502A1 (fr) 2012-10-19 2014-04-24 Bayer Cropscience Ag Combinaisons de composés actifs comprenant des dérivés carboxamide

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Cited By (14)

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EP1836894A1 (fr) 2006-03-25 2007-09-26 Bayer CropScience GmbH Nouvelles formulations solides à base de sulfonamides
EP1844654A1 (fr) 2006-03-29 2007-10-17 Bayer CropScience GmbH Activateur de la pénétration foliaire des principes actives agrochimiques
DE102007013362A1 (de) 2007-03-16 2008-09-18 Bayer Cropscience Ag Penetrationsförderer für herbizide Wirkstoffe
WO2011076731A1 (fr) 2009-12-23 2011-06-30 Bayer Cropscience Ag Formulation liquide de 2-iodo-n-[(4-méthoxy-6-méthyl-1, 3, 5-triazin-2-yl) carbamoyl] benzène sulfonamide
WO2012110517A1 (fr) 2011-02-15 2012-08-23 Bayer Cropscience Ag Combinaisons synergiques contenant un fongicide dithiino-tétracarboxamide et un herbicide, un phytoprotecteur ou un régulateur de croissance végétale
DE102011080020A1 (de) 2011-07-28 2012-09-13 Bayer Cropscience Ag Verwendung von Saatgutbehandlungs-Wirkstoffen aus der Gruppe der Dicarboximid-Fungizide als Safener
DE102011080004A1 (de) 2011-07-28 2012-09-13 Bayer Cropscience Ag Verwendung von Saatgutbehandlungs-Wirkstoffen aus der Gruppe der Carbamat-Fungizide als Safener
DE102011079991A1 (de) 2011-07-28 2012-09-13 Bayer Crop Science Ag Verwendung von Saatgutbehandlungs-Wirkstoffen aus der Gruppe der Nicotinoid-Insektizide als Safener
DE102011079997A1 (de) 2011-07-28 2012-09-13 Bayer Corpscience Ag Verwendung von Saatgutbehandlungs-Wirkstoffen aus der Gruppe der Pyrazol-Insektizide als Safener
DE102011080007A1 (de) 2011-07-28 2012-09-13 Bayer Cropscience Ag Verwendung von Saatgutbehandlungs-Wirkstoffen aus den Gruppen der Conazole- und Triazol-Fungizide als Safener
DE102011080016A1 (de) 2011-07-28 2012-10-25 Bayer Cropscience Ag Verwendung von Saatgutbehandlungs-Wirkstoffen aus der Gruppe der Strobilurin-Fungizide als Safener
DE102011080001A1 (de) 2011-07-28 2012-10-25 Bayer Cropscience Ag Verwendung von Saatgutbehandlungs-Wirkstoffen aus der Gruppe der Carbamat-Insektizide als Safener
DE102011080010A1 (de) 2011-07-28 2012-10-25 Bayer Cropscience Ag Verwendung von Saatgutbehandlungs-Wirkstoffen aus den Gruppen der Anilid- und Thiazol-Fungizide als Safener
WO2014060502A1 (fr) 2012-10-19 2014-04-24 Bayer Cropscience Ag Combinaisons de composés actifs comprenant des dérivés carboxamide

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