WO1981000563A1 - Acides pyridinyloxyphenoxy alcenoiques inferieurs leurs esters ou amides utilises comme desherbants selectifs - Google Patents

Acides pyridinyloxyphenoxy alcenoiques inferieurs leurs esters ou amides utilises comme desherbants selectifs Download PDF

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Publication number
WO1981000563A1
WO1981000563A1 PCT/US1979/000648 US7900648W WO8100563A1 WO 1981000563 A1 WO1981000563 A1 WO 1981000563A1 US 7900648 W US7900648 W US 7900648W WO 8100563 A1 WO8100563 A1 WO 8100563A1
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WO
WIPO (PCT)
Prior art keywords
compound
compounds
phenoxy
och
formula
Prior art date
Application number
PCT/US1979/000648
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English (en)
Inventor
J Ting
Original Assignee
Du Pont
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 Du Pont filed Critical Du Pont
Priority to PCT/US1979/000648 priority Critical patent/WO1981000563A1/fr
Priority to BR8005226A priority patent/BR8005226A/pt
Priority to DK335580A priority patent/DK335580A/da
Priority to ZA00805165A priority patent/ZA805165B/xx
Priority to AU61629/80A priority patent/AU6162980A/en
Priority to EP80302934A priority patent/EP0024907A1/fr
Priority to NZ194739A priority patent/NZ194739A/xx
Priority to GR62725A priority patent/GR70076B/el
Priority to ES80494434A priority patent/ES8106295A1/es
Publication of WO1981000563A1 publication Critical patent/WO1981000563A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C07D213/643—2-Phenoxypyridines; Derivatives thereof
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles

Definitions

  • This invention relates to pyridyloxyphenoxycrotonate esters which are useful as selective weed control agents.
  • the compounds are especially useful for controlling grass weeds in broadleaf crops such as soybeans.
  • the presence of undesirable vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food and fiber needs, such as cotton, rice, corn, wheat, soybean and the like.
  • the current population explosion and concomitant world food and fiber shortage underlie the need for improvements in the efficiency of producing these crops. Preventing or minimizing the loss of a portion of such valuable crops by killing or inhibiting the growth of undesired vegetation is one way of improving this efficiency.
  • R. is alkylene or alkenyl of up to 5 carbon atoms
  • Unexamined Japanese Patent 3,130,672 assigned to Ishihara Industries KK and dated April 18, 1977, claims phenoxy valeric acid derivatives such as
  • German Patent 2,812,571 assigned to Ishihara Sangyo and dated July 21, 1977, claims phenoxy pyridine derivatives of the type represented by the formula:
  • X F or Cl
  • Y H or Cl
  • n 0, 1 or 2.
  • This invention relates to novel compounds of Formula I, to their agricultural compositions and to their method of use as pre— and postemergence herbicides.
  • X is H, Cl or Br; Y is CF 3 or Cl;
  • R ⁇ is H,-CH 3 ,-CH 2 CH 3 or-CH 2 OCH 3 ;
  • R 2 is-OR 3 ,-NR 4 R 5 or-SR 6 ;
  • R 3 is H, C 1 -C 4 alkyl, -CH 2 CH 2 OCH 3 , -CH 2 CH 2 OCH 2 CH 3 or -CH 2 CH 2 CH 2 OCH 3 ;
  • R 4 is H, C 1 -C 3 alkyl, or-OCH 3 ;
  • R 5 is H, or C 1 -C 3 alkyl;
  • R 6 is C 1 -C 4 alkyl; provided that when R 4 is -OCH 3 then R 5 is CH 3 .
  • This invention also relates to agriculturally suitable salts of the above described compound where
  • R 2 is-OR 3 and R 3 is hydrogen.
  • R 1 is CH 3 ; or R 2 is OR 3 ; or X is H or Cl.
  • R 1 is CH 3 and R 2 is OR 3 .
  • R 1 is CH 3 ;
  • R 2 is OR 3 ;
  • X is H or Cl.
  • OR 3 can be prepared, as shown in Equation A, by the reaction of a substituted phenol of the Formula II, wherein X and Y are as defined hereinbefore,
  • Suitable bases include an alkali metal or alkali earth metal hydroxide, hydride, carbonate, bicarbonate or alkoxide, for example, sodium methoxide or potassium t-butoxide.
  • the base is present in an amount of about 1 to 2 molar times the amount of the compound of Formula II.
  • the reaction can be carried out in an organic solvent such as methyl- ethyl ketone, tetrahydrofuran, dimethylformamide, dimethylsulfoxide, or dioxane at temperatures about 20°-100°C, preferably about 25°-80°C.
  • an organic solvent such as methyl- ethyl ketone, tetrahydrofuran, dimethylformamide, dimethylsulfoxide, or dioxane
  • pressure is not critical since pressures above and below atmospheric are suitable. For convenience, atmospheric pressure is preferred.
  • the compounds of Formula II are known in the art, for example, in the teachings of U.S. 4,046,553 and Belgian Patent 865,136, the disclosures of which are hereby incorporated by reference.
  • the substituted alkenoic acid derivatives of Formula III are prepared according to the teachings of Justis Liebigs Annalen Per. Chemie 576, 155 (1952) and Otdel. Khim. Nauk. 1512 (1960), also hereby incorporated by reference.
  • R 2 is OR 3 and R 3 is H and where X, Y and R 1 are as defined hereinbefore, can be prepared by the acidic hydrolysis of the compounds of Formula I with hydrochloric acid or sulfuric acid, or by the basic hydrolysis of the compounds of Formula (I) with sodium hydroxide, potassium hydroxide, or barium hydroxide followed by acidification with hydrochloric acid or sulfuric acid.
  • the preparation of the compounds of Formula IV can be carried out in a solvent such as a mixture of methanol and water, or of ethanol and water at temperatures of about 25-100°C.
  • R 2 is NR 4 R 5 and where X, Y, R 1 , R 4 and R 5 are as defined hereinbefore, can be prepared by contacting the corresponding acid chloride with the proper amine.
  • the amine is present in an amount of about two molar times the amount of acid chloride.
  • the reaction can be carried out neat or in an organic solvent such as methylene chloride, chloroform, tetra- hydrofuran, or dioxane at ambient temperature.
  • the acid chloride can be prepared by reacting the compounds of Formula IV with thionyl chloride, a method known in the art.
  • the compounds of Formula VI are examples of the compounds of Formula VI,
  • R 2 is SR 6 and where X, Y, R. and R 6 are as defined hereinbefore, can be obtained by reacting the corresponding acid chloride of the compounds of Formula IV with the proper mercaptan in the presence of a base.
  • the acid chloride, the compound of Formula IV and the base are typically present in approximately equimolar proportions .
  • the reaction can be carried out in an organic solvent such as methylene chloride, tetrahydrofuran or toluene.
  • the reaction can be carried out at temperatures between about 0° and 100°C, preferably between about 25° and 50°C.
  • the base used for the preparation of the compounds of Formula VI can be a tertiary organic amine such as trimethylamine, triethylamine, N,N-dimethylaniline or pyridine, or alkali metal or alkali earth metal carbonate or bicarbonate.
  • a tertiary organic amine such as trimethylamine, triethylamine, N,N-dimethylaniline or pyridine, or alkali metal or alkali earth metal carbonate or bicarbonate.
  • Agriculturally suitable salts of compounds of Formula I are also useful herbicides and can be prepared by a number of ways known to the art.
  • metal salts can be made by treating compounds of Formula I wherein R 2 is OR 3 and R 3 is hydrogen with a solution of an alkali or alkaline earth metal salt having a sufficiently Basir anion (e.g. hydroxide, alkoxide, carbonate or hydride), Ammonium, amine, and quaternary amine salts can be made by similar techniques.
  • Basir anion e.g. hydroxide, alkoxide, carbonate or hydride
  • Ammonium, amine, and quaternary amine salts can be made by similar techniques.
  • Salts of compounds of Formula I wherein R 2 is OR 3 and R 3 is hydrogen can also be prepared by exchange of one cation for another.
  • Cationic exchange can be effected by direct treatment of an aqueous solution of a salt of a compound of Formula I (e.g. alkali metal or quaternary ammonium salt) with a solution containing the cation to be exchanged. This method is most effective when the desired salt containing the exchanged cation is insoluble in water and can be separated by filtration.
  • Exchange may also be effected by passing an aqueous solution of salt of a compound of Formula I (e.g.
  • carboxylic acid salts By treatment of the appropriate carboxylic acid with a suitable base such as ammonia, an amine, quaternary ammonium hydroxide, or alkali metal or alkaline earth hydroxide, hydride, carbonate, or bicarbonate, the following carboxylic acid salts may be prepared by the method of Example V.
  • a suitable base such as ammonia, an amine, quaternary ammonium hydroxide, or alkali metal or alkaline earth hydroxide, hydride, carbonate, or bicarbonate
  • N,N-Dimethyl-4-[4-[5-(trifluoromethyl)-2-pyridinyloxy]- phenoxy]-2-pentenamide The following procedure can be employed to make the title compound. To 6.6 g of 4-[4-[5-(trifluoromethyl)-2- pyridinyloxy]phenoxy]-2-pentenoic acid in 20 ml of methylene chloride add dropwise 2.6 g of thionyl chloride. Stir the mixture at room temperature for 5 hours and concentrate under vacuum to yield 4- [4- [5- (trifluoromethyl)- 2- ⁇ yridinyloxy]phenoxy]-2-pentenoyl chloride.
  • Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsions, 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 pints to several hundred gallons per acre. High-strength compositions are primarily used as intermediates for further formulation.
  • the formulations broadly, contain about 1% to 99% by weight of active ingredient fsf and at least one of aj about 0.1% to 20% surfactant (s) and b) about 1% to 99% solid or liquid diluent (s). More specifically, they will contain these ingredients in the following approximate proportions:
  • Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd. Edn., Dorland Books, Caldwell, N.J. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts.
  • Typical liquid diluents and solvents are described in Marsden, “Solvent Guide”, 2nd. Edn., Interscience, New York., 1950. Solubility under Q.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, Dec. 4, 1967, pp. 147ff. and "Perry*s Chemical Engineer's Handbook",4th Edn McGraw-Hill, N.Y., 1963, pp. 8-59ff. For further information regarding the art of formulation, see for example;
  • the ingredients are thoroughly blended, passed th-rough a hammer mill and sifted through a U.S.S. No. 50 sieve (0.3 mm openings) before packaging.
  • the ingredients are stirred together to make a solution for direct low-volume application.
  • Example B 10% attapulgite granules (Q.71/0.30mm) 90% The solution is sprayed upon the preformed clay granules in a double-cone blender.
  • the ingredients are combined and stirred with gentle warming to speed mixing.
  • a fine-screen filter is included in the packaging operation to xfemove any extraneous undissolved material.
  • Compositions can contain, in addition to the active ingredients of this invention, other conventional agricultural chemicals such as fertilizers, plant growth modifiers or herbicides.
  • the compounds of Formula I can be combined with ihe following herbicides:
  • the compounds of Formula I can also be combined with other herbicides and are particularly useful in combination with bromacil [3-(sec-butyl)-5- bromo-6-methyluracil], diuron 13, (3,4-dichlorophenyl) . - 1, 1-dimethylurea] , 3-cyclohexyl-1-methyl-6-dimethyl- amino-s-triazine-2,4 (1H,3H)-dione, paraquat
  • the agricultural chemicals listed above are examplary of the compounds which can be mixed with the active compounds and are not intended to limit the invention in any way.
  • Use The compounds of the present invention are useful when applied as pre- and/or post-emergence treatments for broad-spectrum control of a wide variety of weed and brush species growing on industrial sites, storage lots, along fences and building foundations, along railroad and utility rights-of-way, etc.
  • the compounds of the invention have utility for weed control in certain crops, such as soybean, cotton, sugarbeets and beans.
  • herbicides are particularly useful for selectivity removing and controlling grass weeds, including volunteer corn, in broadleaf crops including soybeans, cotton, sugarbeets, beans, flax, cabbage, tomatoes, potatoes, peanuts, carrots, cucurbits, endive, beets etc.
  • Grassweeds include crabgrass, foxtail, barnyardgrass, wild oats, johnsongrass, fall panicum, cheatgrass, quackgrass, and orchardgrass.
  • Compounds of this invention show a remarkable and unexpected degree of safety to broadleaf crops and an unusual phytotoxicity to grass weeds whether applied to the soil before weeds and crops emerge, that is, preemergence, or whether applied postemergence including spraying on the weeds and crops.
  • the compounds are useful when applied as preemergence or postemergence treatments alone and in combination with other herbicides or surfactants for broad-spectrum control of a wide variety of weeds and brush species growing on industrial sites, on storage lots and along fences, building foundations, railroad, highway and utility rights-of-way etc.
  • the precise amount of the compounds of this invention to be used in any particular situation will vary widely according to the end result desired. Factors effecting the optimum rate of application include the plant species to be controlled, soil type, formulation used, prevailing weather conditions, foliage density, length of time for which residual activity is desired, etc. Broadly speaking, the compounds are used at levels at about 0.06 to 20 kilograms per hectare, preferably approximately 0.125 to 5 kilograms per hectare. In general, the higher rates of application from within this range will be selected for adverse conditions or where extended persistence in soil is desired, and the lower rates for weed control in crops.
  • combination treatments consisting of compounds of this invention with other herbicides effective on broadleaf weeds may be used to advantage.
  • Combination treatments may be used with the components applied simultaneously as in a tank mix or mixed formulation, or sequentially with either or both components applied preplant incorporated, preemergence, postemergence, postemergence-directed, broadcast, band or spot treatment or any combination of these methods.
  • the following examples of combination utility are cited: Compounds of this invention with Other Herbicide Use bentazon (post-) Soybeans 2,4-DB (post-) Peanuts, Soybeans Alfalfa, Clover
  • Treated plants and controls were maintained in a greenhouse for sixteen days . All species were compared to controls and visually rated for response to treatment seven and sixteen days after treatment.

Abstract

Esters de pyridyloxyphenoxycrotonate herbicides, par exemple, methyl 4-(4-(5-(trifluoromethyl)-2-pyridiny)oxy)phenoxy)-2-pentenoate, compositions herbicides contenant ces composes, methodes d'utilisation de ces composes comme herbicides et procedes pour la preparation de ces composes.
PCT/US1979/000648 1979-08-23 1979-08-23 Acides pyridinyloxyphenoxy alcenoiques inferieurs leurs esters ou amides utilises comme desherbants selectifs WO1981000563A1 (fr)

Priority Applications (9)

Application Number Priority Date Filing Date Title
PCT/US1979/000648 WO1981000563A1 (fr) 1979-08-23 1979-08-23 Acides pyridinyloxyphenoxy alcenoiques inferieurs leurs esters ou amides utilises comme desherbants selectifs
BR8005226A BR8005226A (pt) 1979-08-23 1980-01-18 Composto herbicida, composicao e processo para o controle de vegetacao indesejavel, composicao e processo para o controle de er vas gramineas em plantas de folhas grandes e processo para preparar um composto herbicida
DK335580A DK335580A (da) 1979-08-23 1980-08-04 Pyridyloxyphenoxycrotonatestere deres fremstilling og anvendelse ved selektiv ukrudtsbekaempelse
ZA00805165A ZA805165B (en) 1979-08-23 1980-08-21 Pyridyloxyphenoxycrotonate esters as selective weed control agents
AU61629/80A AU6162980A (en) 1979-08-23 1980-08-21 Pyridyloxyphenoxycrotonate esters
EP80302934A EP0024907A1 (fr) 1979-08-23 1980-08-22 Dérivés de l'acide pyridyloxyphénoxycrotonique, leur préparation, compositions les contenant et leur utilisation comme herbicides sélectifs
NZ194739A NZ194739A (en) 1979-08-23 1980-08-22 Pyridyloxyphenoxycrotonate ester selective weed control agents
GR62725A GR70076B (fr) 1979-08-23 1980-08-22
ES80494434A ES8106295A1 (es) 1979-08-23 1980-08-22 Un procedimiento para la preparacion de derivados del acido piridiloxifenoxicrotonico.

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
PCT/US1979/000648 WO1981000563A1 (fr) 1979-08-23 1979-08-23 Acides pyridinyloxyphenoxy alcenoiques inferieurs leurs esters ou amides utilises comme desherbants selectifs
WOUS79/00648 1979-08-23
US8000041 1980-01-18

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WO1981000563A1 true WO1981000563A1 (fr) 1981-03-05

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4448965A (en) * 1982-08-16 1984-05-15 Zoecon Corporation Substituted cycloalkanediones
US4448966A (en) * 1982-08-06 1984-05-15 Zoecon Corporation Substituted 2-pyridyloxyphenoxy-alkanetriones
US4508906A (en) * 1982-09-30 1985-04-02 Zoecon Corporation 3-Amino-4-(2-pyridyloxy)phenoxyalkanoic and alkenoic acid esters
US4529438A (en) * 1982-03-23 1985-07-16 Zoecon Corp. Pyridyloxy-phenoxy-alkanoic acid esters and derivatives

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3207760A (en) * 1962-04-10 1965-09-21 S B Penick & Company S-(2-pyridyl-1-oxide)-thioarylates
US4046553A (en) * 1974-10-17 1977-09-06 Ishihara Sangyo Kaisha, Ltd. Herbicidal compound, herbicidal composition containing the same and method of use thereof

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3207760A (en) * 1962-04-10 1965-09-21 S B Penick & Company S-(2-pyridyl-1-oxide)-thioarylates
US4046553A (en) * 1974-10-17 1977-09-06 Ishihara Sangyo Kaisha, Ltd. Herbicidal compound, herbicidal composition containing the same and method of use thereof

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4529438A (en) * 1982-03-23 1985-07-16 Zoecon Corp. Pyridyloxy-phenoxy-alkanoic acid esters and derivatives
US4448966A (en) * 1982-08-06 1984-05-15 Zoecon Corporation Substituted 2-pyridyloxyphenoxy-alkanetriones
US4448965A (en) * 1982-08-16 1984-05-15 Zoecon Corporation Substituted cycloalkanediones
US4508906A (en) * 1982-09-30 1985-04-02 Zoecon Corporation 3-Amino-4-(2-pyridyloxy)phenoxyalkanoic and alkenoic acid esters

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