WO1988002598A1 - Melanges herbicides - Google Patents

Melanges herbicides Download PDF

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Publication number
WO1988002598A1
WO1988002598A1 PCT/US1987/002558 US8702558W WO8802598A1 WO 1988002598 A1 WO1988002598 A1 WO 1988002598A1 US 8702558 W US8702558 W US 8702558W WO 8802598 A1 WO8802598 A1 WO 8802598A1
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WO
WIPO (PCT)
Prior art keywords
compound
undesired vegetation
mixture
crop
postemergence
Prior art date
Application number
PCT/US1987/002558
Other languages
English (en)
Inventor
Timothy T. Obrigawitch
Kent M. Reasons
Original Assignee
E.I. Du Pont De Nemours And Company
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 E.I. Du Pont De Nemours And Company filed Critical E.I. Du Pont De Nemours And Company
Publication of WO1988002598A1 publication Critical patent/WO1988002598A1/fr
Priority to KR1019880700651A priority Critical patent/KR880701525A/ko

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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
    • 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
    • A01N43/22—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 rings with more than six members
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof

Definitions

  • the present invention relates to herbicidal mixtures for crop plants that more effectively control weeds. These mixtures permit lower use rates or reduce phytotoxicity to the crop plants.
  • the control of undesired vegetation is extremely important in achieving high crop efficiency.
  • the selective control of the growth of weeds in such useful crops as rice, soybeans, sugarbeets, peanuts or cotton, to name a few is a desirable achievement. Unchecked weed growth in such useful crops can cause significant losses, reduction of profits to farmers and increasing costs to consumers. There are many products commercially available for these purposes but the search continues for products which are more effective, less costly and safe.
  • U.S. 4,420,325 discloses herbicidal sulfonylureas, including Compound 3.
  • U.S. 4,487,945 teaches the process of preparing a cineole intermediate of Compounds 1 and 2, whose total synthesis is taught in EP-A 81,893, published on June 22, 1983.
  • GB-A-2,042.639 discloses herbicidal quinoxylines, including Compound 7.
  • GB-A-2,134,391, published August 15, 1984 discloses mixtures of Compound 1 with either metr ibuzin or cyanazine.
  • U.S. 4,481,029 discloses herbicidal sulfonylureas which include Compound 19 of the present invention but not the mixtures of the invention.
  • the invention relates to herbicidal mixtures comprising 2-exo-(2-methylbenzyloxy)-1-methyl-4-(1- methylethyl)-7-oxabicyclo[2.2.1]heptane.
  • Compound 1 or 2-exo-)2-bromobenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane.
  • Compound 2 with another herbicide.
  • the invention includes herbicidal mixtures of 1-methyl-4-(1-methylethyl)-2-exo-[(2-methylphenyl)- methoxy]-7-oxabicyclo[2.2.1]heptane, Compound 1; or 1-methyl-4-(1-methylethyl)-2-exo-[(2-bromophenyl)- methoxy]-7-oxabicyclo[2.2.1]heptane, Compound 2, with herbicidal compounds selected from (a) 2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]- aminosulfonylmethyl]benzoic acid, methyl ester.
  • This invention also includes mixtures of 2-exp-(2-methylbenzyloxy)-1-methyl-4-(1-methylethyl)- 7-oxabicyclo[2.2.1]heptane, Compound 1; or
  • Compound 7 Preferred for their improved crop safety, reduced use rates or superior weed control are:
  • compositions of the above mixtures Preferred for their crop safety, reduced use rates or superior weed control are:
  • composition comprising Compound 1 and Compound 3. 25. The composition comprising Compound 1 and
  • composition comprising Compound 1 and Compound 8.
  • composition comprising Compound 1 and Compound 9.
  • composition comprising Compound 1 and Compound 10.
  • composition comprising Compound 1 and Compound 13.
  • composition comprising Compound 1 and Compound 14.
  • composition comprising Compound 1 and Compound 15 .
  • the compos ition compr is ing Compound 1 and Compound 16. 38. The composition comprising Compound 1 and
  • composition comprising Compound 1 and Compound 18.
  • composition comprising Compound 1 and Compound 19.
  • composition comprising Compound 1 and Compound 20.
  • composition comprising Compound 2 and Compound 7.
  • the invention includes the method of controlling the growth of undesired vegetation which comprises applying to the locus of the crop to be protected mixtures of Compound 1 or 2 with certain other herbicides to provide improved spectrum of control or control at lower use rates with reduced crop injury.
  • Preferred for their crop safety, reduced use rates or superior weed control are:
  • a method of use for selectively preventing or killing a weed of a paddy rice crop comprising applying a mixture of compounds
  • a method of Preferred 51 wherein the crop is a broadleaf crop such as soybeans. sugarbeets, peanuts or cotton.
  • a method of use comprising selectively killing or preventing a grass weed in a broadleaf crop by applying a mixture of
  • a method of use comprising selectively killing or preventing a weed in a broadleaf crop such as soybeans by applying a mixture of Compound 1 with a compound selected from
  • a method of use f or select ively ki l l ing or preventing a weed in a crop such as corn comprising applying a mixture of Compound 1 with one of Compounds 16 to 20.
  • the instant mixtures when applied postemergent to the crop and either pre- or postemergent to the undesired vegetation provide improved crop safety, reduced rates or superior weed control, than the individual components alone.
  • the mixtures of the invention provide both the control of existing vegetation and newly germinating weeds. By using these mixtures, the amount of each herbicide may be reduced or the spectrum and length of control improved. In other instances, the mixture may provide the needed weed control while reducing or eliminating phytotoxicity to the crop.
  • the compounds within the mixtures of the present invention are known herbicidal compounds and the method for their production is already well known.
  • Compound 3 can be prepared by the method described in U.S. 4,420,325.
  • Compound 4 can be prepared by the method described in laid open Japanese Application 59-122488, laid open July 14, 1984.
  • Compound 5 can be prepared by the method described in laid open Japanese Application 60-197676, published October 7. 1985.
  • Compound 6 can be prepared by the method described in laid open Japanese Application 60-193983, published October 2, 1985.
  • Compound 7 can be prepared by the method described in GB-A-2.042, 639 (Nissan).
  • Useful formulations of the mixture of Compounds 1 or 2 with Compounds 3 to 20 can be prepared in conventional ways . They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. 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 99% by weight of the active ingredient mixture and at least one of (a) about 0.1% to 20% surfactant (s) and (b) about 1% to 99.9% solid or liquid inert diluent(s).
  • the active ingredient mixture comprises either Compound 1 or 2 and one of Compound 3 to 20 and usage of the combination in a ratio from about 1:0.1 to 1:100 provides a synergistic effect.
  • Proportions in which to use the mixtures of compounds of the present invention may optionally be selected within the range substantially not impairing excellent field weed control effect and phytotoxicity reducing effect with the herbicidal mixture of the present invention. More specifically, they will contain these ingredients in the following approximate proportions:
  • Emulsions, Solutions, (including Emulsifiable Concentrates) Aqueous Suspension 10-50 40-84 1-20
  • Surfactant or a Diluent equals 100 weight percent. Lower or higher levels of the active ingredient mixture can. of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desirable, and are achieved by incorporation into the formulation or by tank mixing.
  • Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, New Jersey, but other solids, either mined or manufactured, may be used. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts.
  • Typical liquid diluents and solvents are described in Marsden. "Solvents Guide.” 2nd Ed., Interscience, New Yorle. 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0°C. "McCutcheon's Detergents and
  • compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example. Littler, U.S. Patent 3,060.084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning, "Agglomeration”, Chemical Engineering. December 4, 1967, pp. 147ff. and “Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff.
  • Example 2 The ingredients are blended, hammer-milled until all the solids are essentially under 50 microns, reblended, and packaged.
  • Example 2 The ingredients are blended, hammer-milled until all the solids are essentially under 50 microns, reblended, and packaged.
  • Compound 1 and Compound 4 (weight ratio 3:1) 50% sodium alkylnaphthalenesulfonate 2% low viscosity methyl cellulose 2% diatomaceous earth 46%
  • Example 3 The ingredients are blended, coarsely hammermilled and then air-milled to produce particles essentially all below 10 microns in diameter. The product is reblended before packaging.
  • Example 3 The ingredients are blended, coarsely hammermilled and then air-milled to produce particles essentially all below 10 microns in diameter. The product is reblended before packaging.
  • Example 4 Extruded Pellet Compound 1 and Compound 5 (weight ratio 1:1) 25% anhydrous sodium sulfate 10% crude calcium ligninsulfonate 5% sodium a lkylnaphthalenesulfonate 1%. calcium/magnesium bentonite 59% The ingredients are blended, hammer-milled and then moistened with about 12% water.
  • the mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled.
  • Compound 1 and Compound 7 (weight ratio 7:1) 80% wetting agent 1% crude ligninsulfonate salt (containing 10% 5 to 20% of the natural sugars) attapulgite clay 9%
  • the ingredients are blended and milled to pass through a 100 mesh screen.
  • This material is then added to a fluid bed granulator, the air flow is adjusted to gently fluidize the material, and a fine spray of water is sprayed onto the fluidized material.
  • the fluidization and spraying are continued until granules of the desired size range are made.
  • the spraying is stopped, but fluidization is continued, optionally with heat, until the water content is reduced to the desired level, generally less than 1%.
  • the material is then discharged, screened to the desired size range, generally 14 to 100 mesh (1410 to 149 microns), and packaged for use.
  • Example 10 The salt is added directly to the water with stirring to produce the solution, which may then be packaged for use.
  • Example 10 The salt is added directly to the water with stirring to produce the solution, which may then be packaged for use.
  • the ingredients are blended and ground in a hammer-mill to produce particles essentially all below 100 microns.
  • the material is sifted through a U.S.S. No. 50 screen and then packaged.
  • Example 12 Wettable Powder Compound 1 and Compound 3 (weight ratio 3:1) 40% sodium ligninsulfonate 20% montmorillonite clay 40%
  • Example 13 Oil Suspension Compound 1 and Compound 3 (weight ratio 4:1) 35% blend of polyalcohol carboxylic 6% esters and oil soluble petroleum sulfonates xylene 59% The ingredients are combined and ground together in a sand mill to produce particles essentially all below 5 microns. The product can be used directly, extended with oils, or emulsified in water.
  • the active ingredient is blended with attapulgite and then passed through a hammer-mill to produce particles substantially all below 200 microns.
  • the ground concentrate is then blended with powdered pyrophyllite until homogeneous.
  • Example 16 Wettable Powder Compound 1 and Compound 7 (weight ratio 1:7) 20% sodium alkylnaphthalenesulfonate 4% sodium ligninsulfonate 4% low viscosity methyl cellulose 3% attapulgite 69% The ingredients are thoroughly blended. After grinding in a hammer-mill to produce particles essentially all below 100 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged.
  • Combinations of Compound 1 with Compound 7 provide unexpectedly good control of weeds such as giant foxtail, johnsongrass. crabgrass and barnyardgrass. And combinations of Compound 1 with Compound 8 provide unexpectedly good control of weeds such as barnyardgrass and giant foxtail.
  • the range of rates for Compound 7 is from 2 to 220 g/ha and for Compound 1 is from 50 to 1500 g/ha.
  • the exact ratio of the two ingredients will depend on the weed species to be controlled and soil type. One with ordinary skill in the art can select the proper ratio.
  • the range of rates of Compound 8 is from 8 to 800 g/ha and for Compound 1. is from 50 to 1500 g/ha.
  • the exact ratio of the two ingredients will depend on the weed species to be controlled and soil type. One with ordinary skill in the art can select the proper ratio.
  • the other mixtures of the present invention may be used to provide weed control in crops such as rice, corn, soybeans, cotton, etc.
  • the range of ratios for the individual compounds is bounded by their synergistic utility and rates can be determined by one skilled in the art based on temperature, rainfall and soil type of the area where mixture is to be used.
  • the range of rates of Compound 9 is from 100 to 100 to
  • 500 g/ha and for Compound 1. is from 50 to 1500 g/ha.
  • the exact ratio of the two ingredients will depend on the weed species to be controlled and soil type. One with ordinary skill in the art can select the proper ratio.
  • the range of rates of Compound 10 is from 50 to
  • 400 g/ha and for Compound 1. is from 50 to 1500 g/ha.
  • the exact ratio of the two ingredients will depend on the weed species to be controlled and soil type. One with ordinary skill in the art can select the proper ratio.
  • the range of rates of Compound 11 is from 50 to 500 g/ha and for Compound 1. is from 50 to 1500 g/ha.
  • the exact ratio of the two ingredients will depend on the weed species to be controlled and soil type. One with ordinary skill in the art can select the proper ratio.
  • the range of rates of Compound 12 is from 50 to
  • 800 g/ha and for Compound 1, is from 50 to 1500 g/ha.
  • the exact ratio of the two ingredients will depend on the weed species to be controlled and soil type. One with ordinary skill in the art can select the proper ratio.
  • the range of rates of Compound 13 is from 50 to
  • 400 g/ha and for Compound 1, is from 50 to 1500 g/ha.
  • the exact ratio of the two ingredients will depend on the weed species to be controlled and soil type. One with ordinary skill in the art can select the proper ratio.
  • the range of rates of Compound 14 is from 50 to 400 g/ha and for Compound 1, is from 50 to 1500 g/ha.
  • the exact ratio of the two ingredients will depend on the weed species to be controlled and soil type. One with ordinary skill in the art can select the proper ratio.
  • the range of rates of Compound 15 is from 200 to 1200 g/ha and for Compound 1. is from 50 to 1500 g/ha.
  • the exact ratio of the two ingredients will depend on the weed species to be controlled and soil type. One with ordinary skill in the art can select the proper ratio.
  • the range of rates of Compound 16 is from 50 to 800 g/ha and for Compound 1. is from 50 to 1500 g/ha.
  • the exact ratio of the two ingredients will depend on the weed species to be controlled and soil type. One with ordinary skill in the art can select the proper ratio.
  • the range of rates of Compound 17 is from 50 to 1000 g/ha and for Compound 1. is from 50 to 1500 g/ha.
  • the exact ratio of the two ingredients will depend on the weed species to be controlled and soil type. One with ordinary skill in the art can select the proper ratio.
  • the range of rates of Compound 18 is from 1 to 280 g/ha and for Compound 1, is from 50 to 1500 g/ha.
  • the exact ratio of the two ingredients will depend on the weed species to be controlled and soil type. One with ordinary skill in the art can select the proper ratio.
  • the range of rates of Compound 19 is from 100 to 2500 g/ha and for Compound 1, is from 50 to 1500 g/ha.
  • the exact ratio of the two ingredients will depend on the weed species to be controlled and soil type. One with ordinary skill in the art can select the proper ratio.
  • the range of rates of Compound 20 is from 250 to 6000 g/ha and for Compound 1, is from 50 to 1500 g/ha.
  • the exact ratio of the two ingredients will depend on the weed species to be controlled and soil type. One with ordinary skill in the art can. select the proper ratio. Additionally, mixtures of Compound 1 or Compound 2 with one of Compounds 8, 9, 10. 11 or 12 will have the same utility as mixtures of Compounds 1 and 7.
  • the utility of this invention also includes the ability of Compound 1 or 2 to reduce the crop injury normally observed with Compounds 3 to 6 when applied to rice. While Compounds 3-6 generally provide good control of broadleaf and sedge weeds, crop injury can be observed. Preparing a mixture of Compound 1 or 2 with any of the other compounds (3-6) not only reduces the injury caused by Compounds 3-6 but also controls barnyardgrass. an important weed species in rice. Notably, mixtures of Compound 1 or 2 with Compounds 3-6 result in reducing the rates of all compounds required for effective weed control below those required for each individual compound alone. In particular, these mixtures provide unexpectedly effective control of water chestnut. Mixtures involving Compound 1 with Compound 3 or 4 are especially effective. Effective rates of Compounds 3 or 4 with Compound 1 range from 10-500 g/ha
  • Example 18 Use of Colby's Equation to Determine Synergism
  • synergism can be defined as the greater-than-expected, or greater-than-additive effect of two compounds when applied in combination as a mixture.
  • the effects of each compound when applied singly against a given pest are determined, as well as the effects of the two compounds applied in combination as a mixture.
  • Colby's equation is used to calculate the effect that would result from an application of the combination of the two if they acted together as expected, or additively.
  • Colby's equation is:
  • the first compound is capable of removing 50% of the pest population
  • the second compound is capable of removing 50% of the remaining population, so a total of 75% of the population is expected to be removed by the combination. If the measured or observed effect of the combination exceeds the value predicted by
  • Resu ts are the means o three replications
  • Example 19 Concrete pot tests were conducted outdoors in 50 x 50 cm pots at Ushiku, Japan. The pots were filled with 6 cm of gravel, 3 cm of sand, and 16 cm of paddy soil (Fujishiro light clay). Weed seeds and tubers were incorporated into the top 2-3 cm of soil. After flooding, Nipponbare rice plants at the 2-leaf stage were transplanted into the pots using three plants per hill and six hills per pot. After transplanting, the water level was maintained at a depth of 3 to 4 cm. Chemicals were formulated in granules so that 30 kg/ha of granules gave the desired dosage. These were spread over the surface of the pots.
  • DAT treatment time (days after transplanting rice).
  • Example 21 These tests were conducted on direct-seeded rice in the field in California in 1987. Treatments were made at the 2-leaf stage of rice as either a foliar spray or granules spread by hand. Granules (G) of Compound 1 and Compound 3 contained 0.5% and 0.32% active ingredient, respectively.
  • the formulation of Compound 1 used for spraying was an emulsifiable concentrate (EC) containing 7 lbs/gallon active ingredient.
  • the formulation of Compound 3 used for spraying was a dry flowable (DF) containing 60 weight % active ingredient.
  • Plots contained 9.0 X 20.0 ft of direct water seeded rice in a water depth of 4 to 6 inches. Evaluations were made 38 days after application and represent an average of four replications. The results are summarized in Table 16.
  • Example 22 Airlite plastic pots (16 cm diameter) were partially filled with Tama silt loam soil and the soil was saturated with water. Japonica (cv. M101) and Indica (cv. Lemont) rice seedlings at the 2.0 to 2.5 leaf stage were transplanted into one-third of the pots. Into another third of the pots were transplanted seedling or sprouted tubers of water plantain (Alisma trivale). Scripus (Scirpus paludosus). Cyperus (Cyperus esculentus), and arrowhead (Sagittaria spp.).
  • the remaining pots were planted with barnyardgrass (Echinochloa crus-galli) seeds and sprouted tubers of water chestnut (Eleocharis spp.). These weeds all represent major rice weeds or genera of weeds important in rice .
  • the water level was raised to 3 cm (about 1200 ml/pot) and maintained at this level throughout the test.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (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)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Mélanges herbicides comprenant un composé d'oxabicycloheptane.
PCT/US1987/002558 1986-10-10 1987-10-09 Melanges herbicides WO1988002598A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR1019880700651A KR880701525A (ko) 1986-10-10 1988-06-09 제초제 혼합물

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
US91817286A 1986-10-10 1986-10-10
US93610486A 1986-11-28 1986-11-28
US936,104 1986-11-28
US8654687A 1987-08-18 1987-08-18
US086,546 1987-08-18
US9549687A 1987-09-16 1987-09-16
US095,496 1987-09-16
US918,172 1992-07-23

Publications (1)

Publication Number Publication Date
WO1988002598A1 true WO1988002598A1 (fr) 1988-04-21

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Application Number Title Priority Date Filing Date
PCT/US1987/002558 WO1988002598A1 (fr) 1986-10-10 1987-10-09 Melanges herbicides

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KR (1) KR880701525A (fr)
WO (1) WO1988002598A1 (fr)

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0456198A1 (fr) * 1990-05-10 1991-11-13 Hodogaya Chemical Co., Ltd. Suspensions d'huiles concentrées pour l'application directe dans l'eau de la rizière
EP0514768A1 (fr) * 1991-05-18 1992-11-25 Hoechst Schering AgrEvo GmbH Dispersions aqueuses des dérivés de sulfonylurée
WO1997016975A1 (fr) * 1994-05-11 1997-05-15 John Selga Composition et procede herbicides
WO2014043156A1 (fr) * 2012-09-13 2014-03-20 Dow Agrosciences Llc Compositions herbicides comprenant de l'aminopyralide et de la bentazone
WO2017009139A1 (fr) * 2015-07-10 2017-01-19 BASF Agro B.V. Composition herbicide à base de cinméthyline et de diméthachlore
WO2017009140A1 (fr) 2015-07-10 2017-01-19 BASF Agro B.V. Composition herbicide à base de cinméthyline et d'acétochlore ou de prétilachlore
WO2017009092A1 (fr) * 2015-07-10 2017-01-19 BASF Agro B.V. Composition herbicide à base de cinméthyline et de métolachlore ou s-métolachlore
WO2017009146A1 (fr) * 2015-07-10 2017-01-19 BASF Agro B.V. Composition herbicide à base de cinméthyline et d'inhibiteurs spécifiques du photosystème ii
WO2017009148A1 (fr) * 2015-07-10 2017-01-19 BASF Agro B.V. Procédé pour lutter contre des mauvaises herbes résistantes ou tolérantes aux herbicides
WO2017009145A1 (fr) * 2015-07-10 2017-01-19 BASF Agro B.V. Composition herbicide à base de cinméthyline et d'inhibiteurs spécifiques de la protoporphyrinogène oxydase
US10375959B2 (en) 2015-01-22 2019-08-13 BASF Agro B.V. Ternary herbicidal combination comprising saflufenacil
US10813356B2 (en) 2015-07-10 2020-10-27 BASF Agro B.V. Herbicidal composition comprising cinmethylin and dimethenamid
US10980232B2 (en) 2015-07-10 2021-04-20 BASF Agro B.V. Herbicidal composition comprising cinmethylin and pyroxasulfone
US11116213B2 (en) 2015-07-10 2021-09-14 BASF Agro B.V. Herbicidal composition comprising cinmethylin and pethoxamid
US11206827B2 (en) 2015-07-10 2021-12-28 BASF Agro B.V. Herbicidal composition comprising cinmethylin and specific quinolinecarboxylic acids
US11219215B2 (en) 2015-07-10 2022-01-11 BASF Agro B.V. Herbicidal composition comprising cinmethylin and specific inhibitors of protoporphyrinogen oxidase
US11219212B2 (en) 2015-07-10 2022-01-11 BASF Agro B.V. Herbicidal composition comprising cinmethylin and imazamox
EP3954212A1 (fr) * 2015-07-10 2022-02-16 BASF Agro B.V. Procédé pour lutter contre les mauvaises herbes tolérantes ou résistantes aux herbicides, composition herbicide et procédé de lutte contre la végétation indésirable
US11291206B2 (en) 2015-07-10 2022-04-05 BASF Agro B.V. Herbicidal composition comprising cinmethylin and specific pigment synthesis inhibitors
US11517018B2 (en) 2015-07-10 2022-12-06 BASF Agro B.V. Herbicidal composition comprising cinmethylin and saflufenacil

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EP0456198A1 (fr) * 1990-05-10 1991-11-13 Hodogaya Chemical Co., Ltd. Suspensions d'huiles concentrées pour l'application directe dans l'eau de la rizière
EP0514768A1 (fr) * 1991-05-18 1992-11-25 Hoechst Schering AgrEvo GmbH Dispersions aqueuses des dérivés de sulfonylurée
AU661687B2 (en) * 1991-05-18 1995-08-03 Bayer Cropscience Ag Aqueous dispersions of sulfonylurea derivatives
US5573998A (en) * 1991-05-18 1996-11-12 Hoechst Aktiengesellschaft Aqueous dispersions of sulfonediamide Herbicides such as amidosulfuron
US5707926A (en) * 1991-05-18 1998-01-13 Hoechst Aktiengesellschaft Aqueous dispersions of sulfonylurea derivatives
WO1997016975A1 (fr) * 1994-05-11 1997-05-15 John Selga Composition et procede herbicides
CN104768381B (zh) * 2012-09-13 2017-10-31 美国陶氏益农公司 包含氯氨吡啶酸和灭草松的除草组合物
WO2014043156A1 (fr) * 2012-09-13 2014-03-20 Dow Agrosciences Llc Compositions herbicides comprenant de l'aminopyralide et de la bentazone
CN104768381A (zh) * 2012-09-13 2015-07-08 美国陶氏益农公司 包含氯氨吡啶酸和灭草松的除草组合物
US10375959B2 (en) 2015-01-22 2019-08-13 BASF Agro B.V. Ternary herbicidal combination comprising saflufenacil
US20180199572A1 (en) * 2015-07-10 2018-07-19 BASF Agro B.V. Herbicidal Composition Comprising Cinmethylin and Metolachlor or S-Metolachlor
AU2016292678B2 (en) * 2015-07-10 2020-12-24 BASF Agro B.V. Method for controlling herbicide resistant or tolerant weeds
WO2017009148A1 (fr) * 2015-07-10 2017-01-19 BASF Agro B.V. Procédé pour lutter contre des mauvaises herbes résistantes ou tolérantes aux herbicides
WO2017009145A1 (fr) * 2015-07-10 2017-01-19 BASF Agro B.V. Composition herbicide à base de cinméthyline et d'inhibiteurs spécifiques de la protoporphyrinogène oxydase
WO2017009092A1 (fr) * 2015-07-10 2017-01-19 BASF Agro B.V. Composition herbicide à base de cinméthyline et de métolachlore ou s-métolachlore
CN107708422A (zh) * 2015-07-10 2018-02-16 巴斯夫农业公司 防治除草剂抗性或耐受性杂草的方法
KR20180027579A (ko) * 2015-07-10 2018-03-14 바스프 아그로 비.브이. 신메틸린 및 아세토클로르 또는 프레틸라클로르를 포함하는 제초제 조성물
CN107835638A (zh) * 2015-07-10 2018-03-23 巴斯夫农业公司 包含环庚草醚和乙草胺或丙草胺的除草组合物
CN107846895A (zh) * 2015-07-10 2018-03-27 巴斯夫农业公司 包含环庚草醚和原卟啉原氧化酶的特异性抑制剂的除草组合物
CN107846894A (zh) * 2015-07-10 2018-03-27 巴斯夫农业公司 包含环庚草醚和特异性光合系统ii抑制剂的除草组合物
WO2017009140A1 (fr) 2015-07-10 2017-01-19 BASF Agro B.V. Composition herbicide à base de cinméthyline et d'acétochlore ou de prétilachlore
JP2018520163A (ja) * 2015-07-10 2018-07-26 ビーエーエスエフ アグロ ベー．ブイ． 除草剤抵抗性又は耐性雑草を防除する方法
JP2018522004A (ja) * 2015-07-10 2018-08-09 ビーエーエスエフ アグロ ベー．ブイ． シンメチリン及びアセトクロール又はプレチラクロールを含む除草剤組成物
WO2017009139A1 (fr) * 2015-07-10 2017-01-19 BASF Agro B.V. Composition herbicide à base de cinméthyline et de diméthachlore
US10813356B2 (en) 2015-07-10 2020-10-27 BASF Agro B.V. Herbicidal composition comprising cinmethylin and dimethenamid
WO2017009146A1 (fr) * 2015-07-10 2017-01-19 BASF Agro B.V. Composition herbicide à base de cinméthyline et d'inhibiteurs spécifiques du photosystème ii
AU2016292643B2 (en) * 2015-07-10 2020-12-24 BASF Agro B.V. Herbicidal composition comprising cinmethylin and specific photosystem II inhibitors
US10897898B2 (en) 2015-07-10 2021-01-26 BASF Agro B.V. Herbicidal composition comprising cinmethylin and acetochlor or pretilachlor
US10980232B2 (en) 2015-07-10 2021-04-20 BASF Agro B.V. Herbicidal composition comprising cinmethylin and pyroxasulfone
US11116213B2 (en) 2015-07-10 2021-09-14 BASF Agro B.V. Herbicidal composition comprising cinmethylin and pethoxamid
US11206827B2 (en) 2015-07-10 2021-12-28 BASF Agro B.V. Herbicidal composition comprising cinmethylin and specific quinolinecarboxylic acids
US11219215B2 (en) 2015-07-10 2022-01-11 BASF Agro B.V. Herbicidal composition comprising cinmethylin and specific inhibitors of protoporphyrinogen oxidase
US11219212B2 (en) 2015-07-10 2022-01-11 BASF Agro B.V. Herbicidal composition comprising cinmethylin and imazamox
EP3954212A1 (fr) * 2015-07-10 2022-02-16 BASF Agro B.V. Procédé pour lutter contre les mauvaises herbes tolérantes ou résistantes aux herbicides, composition herbicide et procédé de lutte contre la végétation indésirable
EP3954211A1 (fr) * 2015-07-10 2022-02-16 BASF Agro B.V. Procédé pour lutter contre les mauvaises herbes tolérantes ou résistantes aux herbicides, composition herbicide et procédé de lutte contre la végétation indésirable
US11291206B2 (en) 2015-07-10 2022-04-05 BASF Agro B.V. Herbicidal composition comprising cinmethylin and specific pigment synthesis inhibitors
EP3987933A1 (fr) * 2015-07-10 2022-04-27 BASF Agro B.V. Procédé de lutte contre les mauvaises herbes résistantes ou tolérantes aux herbicides, composition herbicide et procédé de lutte contre la végétation indésirable
AU2021200737B2 (en) * 2015-07-10 2022-08-25 BASF Agro B.V. Method for controlling herbicide resistant or tolerant weeds
US11517018B2 (en) 2015-07-10 2022-12-06 BASF Agro B.V. Herbicidal composition comprising cinmethylin and saflufenacil
KR102549057B1 (ko) 2015-07-10 2023-06-29 바스프 아그로 비.브이. 신메틸린 및 아세토클로르 또는 프레틸라클로르를 포함하는 제초제 조성물
CN107846895B (zh) * 2015-07-10 2024-04-19 巴斯夫农业公司 包含环庚草醚和原卟啉原氧化酶的特异性抑制剂的除草组合物
CN107846894B (zh) * 2015-07-10 2024-05-28 巴斯夫农业公司 包含环庚草醚和特异性光合系统ii抑制剂的除草组合物

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