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WO1993012109A1 - Derive d'acide picolinique, production de ce derive, et herbicide - Google Patents

Derive d'acide picolinique, production de ce derive, et herbicide Download PDF

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Publication number
WO1993012109A1
WO1993012109A1 PCT/JP1991/001725 JP9101725W WO9312109A1 WO 1993012109 A1 WO1993012109 A1 WO 1993012109A1 JP 9101725 W JP9101725 W JP 9101725W WO 9312109 A1 WO9312109 A1 WO 9312109A1
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WIPO (PCT)
Prior art keywords
group
formula
atom
alkyl
represented
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/JP1991/001725
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English (en)
Japanese (ja)
Inventor
Fumiaki Takabe
Yoshihiro Saito
Masatoshi Tamaru
Shigehiko Tachikawa
Ryo Hanai
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ihara Chemical Industry Co Ltd
Kumiai Chemical Industry Co Ltd
Original Assignee
Ihara Chemical Industry Co Ltd
Kumiai Chemical Industry Co Ltd
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 Ihara Chemical Industry Co Ltd, Kumiai Chemical Industry Co Ltd filed Critical Ihara Chemical Industry Co Ltd
Priority to PCT/JP1991/001725 priority Critical patent/WO1993012109A1/fr
Priority to HU9201294A priority patent/HU213623B/hu
Priority to RO92-200527A priority patent/RO109848B1/ro
Priority to PL91295868A priority patent/PL169374B1/pl
Priority to SU915011967A priority patent/RU2091380C1/ru
Priority to BR919106704A priority patent/BR9106704A/pt
Publication of WO1993012109A1 publication Critical patent/WO1993012109A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • 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
    • A01N47/02—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 no bond to a nitrogen atom
    • A01N47/06—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 no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues 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
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings

Definitions

  • the present invention relates to a novel picolinic acid derivative useful as a herbicide and a herbicide containing the same, which can be applied to paddy fields, fields, non-agricultural lands, and the like.
  • the present inventors have conducted intensive studies on picolinic acid derivatives in order to solve these problems.
  • dialkylamine was added to pyridin ⁇ of pyrimidinyloxypicopolinic acid derivatives.
  • the compound of the present invention into which the substituents such as described above are introduced has a wide range of herbicidal spectrum which shows an excellent effect on annual and perennial grasses and broadleaf grasses at extremely low doses. And completed the present invention. .
  • the picolinic acid derivative of the present invention has the general formula
  • R is a hydrogen atom, an alkyl (C 1-4) group, an alkenyl (C 2 -C 4) group, an alkynyl (C 2 -C 4) group, a benzyl group, a phenyl group, C 1 -C 4 groups, cyanoalkyl (C 1 -C 4) groups, alkoxy (C 1 -C 4) alkyl (C 1 -C 4) groups, alkoxy (C 1 -C 4) carponyloxyalkyl ( 1 to 4 carbon atoms) Algishi (1 to 4 carbon atoms) carbonyl alkyl (1 to 4 carbon atoms) group, alkylcarbonyl (2 to 7 carbon atoms) oxyalkyl (1 to 4 carbon atoms) group, cyclo Alkyl carbonyl (C 4-7) 4) group, cycloalkyl (C3-6) ⁇ / lekyl (C1-4) group, alkali metal atom; for example, alkaline
  • R and R 2 are the same or different and each represents a lower alkyl group, a lower alkoxy group, a nitrogen-substituted lower alkoxy group, an alkylsulfonyl (C 1 -C 4) group or a halo group; Indicates a halogen atom,
  • X is the formula N ⁇
  • R 3 and R 4 are the same or different and each represent a hydrogen atom, a lower alkyl group, a phenyl group or a acyl group.
  • a cyano group, a phenyl group Group (the group may be substituted by a nitrogen atom, a lower alkyl group or a lower alkoxy group), a phenoxy group, a nitrogen-substituted alkyl (carbon number 1-4) groups, alkoxy (1-4 carbons) groups, alkenyl
  • Y is an oxygen atom, a sulfur atom or a formula
  • R 5 represents a hydrogen atom or a formyl group.
  • n represents 0 or 1.
  • Y represents a group represented by the formula _N ⁇ . )].
  • lower alkyl groups include methyl, ethyl, propyl, butyl, etc.
  • lower alkoxy groups include methoxyethoxy, propoxy, butoxy, etc., and cycloalkyl.
  • the group include cyclopropinole, cyclopentisole, and cyclohexyl.
  • the acyl group include a formyl group and an alkyl carbonyl group, and an example of an azole carbonyl group.
  • Examples include acetinole, propionole, petilyl, norrelyl, pinolyl, hexamyl, and the like, and further, as nitrogen atoms, kurozole, brom, Fluoro and the like.
  • Examples of the salt of the picolinic acid derivative include hydrochloric acid, sulfuric acid, and oxalate.
  • Examples of the method for producing the compound of the present invention include, for example, the following methods, but are not limited to these methods.
  • R s is shows the R other than a hydrogen atom
  • L is Nono b gain down
  • Y ′ represents
  • the compound represented by the formula [I-11] is obtained by converting a compound represented by the formula [ ⁇ ] and a pyrimidine derivative represented by the formula [m] to a base.
  • an inert solvent preferably at room temperature or within the temperature range of the boiling point of the solvent, for a few minutes to several hours.
  • the solvent include hydrocarbon solvents such as benzene and toluene, and halogenated hydrocarbons such as dichloromethane and chlorohonolem.
  • Solvents such as ether solvents such as tetrahydrofuran, 1,4-dioxane, etc., ketone solvents such as aceton, methylethyl ketone, etc., methyl acetate, acetic acid Estel solution such as ethyl Solvents, non-protonic polar solvents such as dimethylformamide, dimethylacetamide, etc., and acetate nitrile can be used.
  • the base include alkali metals such as sodium metal and potassium metal, and alkali metal hydride such as sodium hydride and potassium hydride calcium hydride. Metals and hydrogenated alkaline earth metals, sodium carbonate, potassium carbonate, calcium carbonate and other carbonates, sodium hydroxide, potassium hydroxide, Metal hydroxides such as calcium hydroxide can be used.
  • a compound in which C H ⁇ or Y is —N H — can be produced by reacting a compound in which Y is —N ⁇ with an acid or a base.
  • the compound represented by the formula [I-13] is obtained by mixing a compound represented by the formula [I-13] with a polar solvent, water or a mixture of a polar solvent and water in the presence of a base. The reaction is carried out in a solvent at room temperature or within the temperature range of the boiling point of the solvent for several hours to tens of hours. Can be built
  • the compound represented by the formula [I-14] can be produced.
  • solvent examples include alcohol solvents such as methanol and ethanol, and 1,4-dioxane and tetrahydrofuran.
  • Amide polar solvents such as ter polar solvents, dimethylformamide and dimethylacetamide can be used, but are not limited thereto.
  • carbonates such as sodium carbonate, potassium carbonate, calcium carbonate and the like, sodium hydroxide, potassium hydroxide, calcium hydroxide Metal hydroxides such as rubber can be used.
  • the compound represented by the formula [I-15] can be prepared by converting the compound represented by the formula [1-3] and the compound represented by the formula [IV] into a polar compound in the presence of a base or in the absence of a base.
  • a solvent preferably an inert solvent, at room temperature or within a temperature range of the boiling point of the solvent for several minutes. By reacting for several hours, it can be re-manufactured.
  • the solvent examples include hydrocarbon solvents such as benzene and toluene, halogenated hydrocarbon solvents such as chloromethane and chloro-form, 1,4-dioxane, and tetrahydrofuran.
  • Ether solvents such as acetone, methyl ketone, etc .
  • ester solvents such as methyl acetate, ethyl acetate; etc., such as dimethyl phenol amide, dimethyl acetate amide, etc.
  • Mid-based non-protonic polar solvents, acetonitrile, etc. can be used.
  • Examples of the base include alkali metals such as sodium metal and potassium metal, and alkali metal hydrides such as sodium hydride, potassium hydride and hydrogen sulfide. And hydrogenated alkaline earth metals, sodium carbonate, carbonates such as calcium carbonate and calcium carbonate, sodium hydroxide, lithium hydroxide, calcium hydroxide Metal hydroxides such as aluminum, and organic bases such as triethylamine, diisopropylethylamine, pyridine and the like can be used.
  • the compound represented by the formula [I-17] is different from the compound represented by the formula [I-17] in an inert solvent at room temperature or within a temperature range of the boiling point of the solvent for several minutes. It can be produced by reacting with acid for several hours.
  • the solvent examples include hydrocarbon solvents such as benzene and toluene, dichloromethane, and nitrogenated hydrocarbon solvents such as chloro-form, 1,4-dioxane, Ether solvents such as transhydran, ketone solvents such as aceton and methyl ketone, ester solvents such as methyl acetate and ethyl acetate, dimethylformamide, dimethyla Amide-based non-protonic polar solvents such as cetamide and acetate nitrile can be used.
  • the acid include hydrochloric acid, sulfuric acid, and oxalic acid. The acid may be added directly to the inert solvent or a gas may be added.
  • the solvent methanol, water, dichloromethane, orifice form and the like are preferable.
  • an organic peroxide such as hydrogen peroxide, methanol perbenzoic acid, or benzoyl peroxide is used.
  • 6- (N, N-dimethylamino) 13-Hydroxypicolinic acid 1.4 g (7 ⁇ mol), 4, 6-dimethyloxy 2-methylsulfonylpyri 16 g (7 ⁇ mozole) of the midine and 0.6 g (4 m mozole) of potassium carbonate were added to 100 mJ of DMF, and reacted at 90 ° C for 2 hours. After completion of the reaction, the mixture is poured into water, extracted with getyl ether, washed with water, dried and concentrated.
  • Example 23 with a yield of 1.6 g (yield 66%) and a melting point of 125 to 127.
  • Example 2 3 (4,6 — dimethyloxypyridine 2 -yl) oxy 6 — Methizole phenylpicolinate (Compound 8) , °
  • Example 3 (4, 6 — dimoxirimidine 1 2 — yl) oxo 1 6 — (N, N — dimethylinomino) picolinic acid
  • the reaction mixture was taken in water and extracted twice with ethyl acetate. After the organic layer was washed with water and dried, the solvent was distilled off, and the obtained viscous substance was subjected to column purification to obtain a target compound.
  • the yield was 0.5 g (yield 33%) and the refractive index (Na-D line) was 1.5215.
  • the starting compound of the present compound can be produced according to the following method.
  • R s is shows the same meaning
  • R 8 is shows the Xia amino group dimethyl Chirua Mi amino group or Jechirua Mi amino group
  • R s is dimethyl Chirua Mi amino group
  • Jechirua Mi Represents a no group, an alkyl group or a phenyl group.
  • the compound represented by the formula [11-1] and the trimethylsilyl derivative represented by the formula [V] or the acid chloride represented by the formula CVI] are not heated at room temperature in an inert solvent. By reacting for several hours within the temperature range of the boiling point of the solvent, the compound represented by the formula [ ⁇ -6] or the formula [H-7] can be produced.
  • the solvent examples include hydrocarbon solvents such as benzene and toluene, halogenated hydrocarbon solvents such as dichloromethane and chlorofozolem, tetrahydrofuran, 1 , 41-Dioxane and other ether solvents, Acetone and methyl ethyl ketone and other ketone solvents, methyl acetate and ethyl acetate and other ester solvents, dimethyl formamide, dimethyl acetate Non- -Protonic polar solvents, other acetonitriles, etc. can be used, but chlorophonolem is preferred.
  • hydrocarbon solvents such as benzene and toluene
  • halogenated hydrocarbon solvents such as dichloromethane and chlorofozolem
  • tetrahydrofuran 1 , 41-Dioxane and other ether solvents
  • Acetone and methyl ethyl ketone and other ketone solvents methyl acetate
  • R s has the same meaning as described above, and R ′ represents an alkyl group, a substituted alkyl group or a 4,6-dimethoxypyrimidinyl group, L 2 represents a halogen atom, provided that when R 1 ° is a 4,6-dimethoxypyrimidinyl group, L 2 represents a nitrogen atom or an alkylsulfonyl group; That is, the compound represented by the formula [ ⁇ -4] and the compound represented by the formula [VI] are mixed in the presence of a base in an inert solvent at room temperature or within the temperature range of the boiling point of the solvent. By reacting for several minutes to several hours, the compound represented by the general formula [I [18]] can be produced.
  • the solvent examples include hydrocarbon solvents such as benzene and toluene, dichloromethane and nitrogen-containing hydrocarbon solvents such as cross-hole form, and tetrahydrocarbons.
  • hydrocarbon solvents such as benzene and toluene, dichloromethane and nitrogen-containing hydrocarbon solvents such as cross-hole form, and tetrahydrocarbons.
  • Ether solvents such as drofuran and 1,4-dioxane
  • ketone solvents such as acetone and methyl ethyl ketone
  • ester solvents such as methyl acetate and ethyl acetate
  • Non-standards such as chill formamide and dimethylacetamide Protonic polar ⁇ solvents, other acetonitrile, etc. can be used.
  • Examples of the base include alkali metals such as sodium metal and potassium metal, and alkali metal hydrides such as sodium hydride and potassium hydride calcium hydride.
  • Metals and hydrogenated Alkaline earth metals, sodium carbonate, potassium carbonate, carbonates such as caneoleum carbonate, sodium hydroxide, sodium hydroxide, calcium hydroxide Metal hydroxides such as aluminum can be used.
  • R s and L 1 have the same meanings as described above, and R 11 represents a substituted phenyl group.
  • the compound represented by the formula [ ⁇ -5] and the compound represented by the formula [VI] are reacted for several hours in the presence of a base and a solvent in an inert solvent within a temperature range from room temperature to the boiling point of the solvent.
  • the compound represented by the general formula [H-9] can be produced.
  • the solvent examples include a hydrocarbon solvent such as benzene and toluene, an after-recording solvent such as methanol and ethanol, and 1,2-dimethoxetane and tetramer.
  • a hydrocarbon solvent such as benzene and toluene
  • an after-recording solvent such as methanol and ethanol
  • 1,2-dimethoxetane and tetramer 1,2-dimethoxetane and tetramer.
  • Hid EI Franc Ethil Ether solvents such as ether, ester solvents such as methyl acetate and ethyl acetate, non-protonic polar solvents such as dimethyl reformamide and dimethinorea set amide, and other solvents Trinitrile can be used.
  • Tetrax triphenylphosphine is used as a catalyst.
  • Radium (0), triphenylinolefos fin and acetate acetate are used, tris (0-tolyl) phosphine and palladium acetate are used. It can.
  • the base include carbonates such as sodium carbonate and potassium carbonate, bicarbonates such as sodium hydrogen carbonate, and triethylamine and pyridin. Organic bases can be used.
  • the starting compound can be produced by the following method.
  • [10] can be produced by reacting the compound of formula [10] with formic acid at room temperature or within the boiling range for several minutes or several hours.
  • acetic anhydride-formic acid mixed solution or diformate It can also be produced by reacting with cyclohexylcarbodiimide.
  • the compound represented by the formula [H—13] is a compound represented by the formula [ ⁇ 12] It can be produced by reacting with sodium nitrite at around 0 ° C in the presence of a mineral acid to form a diazonium salt, and then treating with sulfuric acid or a sulfur compound. it can.
  • sulfur compound examples include inorganic compounds such as sodium sulfide and sodium hydrosulfide, and organic compounds such as benzylmelkabutane and diethyl carbonate. However, it is not limited to these methods.
  • a 100-111 £ capacity 3-port flask with thermometer, cooling pipe and nitrogen inlet pipe is equipped with a tedrox (tri-enisole phos fin).
  • a tedrox tri-enisole phos fin
  • 2-dimethoxybenzene 5 mJ2 2-dimethoxybenzene 5 mJ2
  • 3-benzyloxy 16-black mouth 2.7 g of methyl picolinate (10.0 m 1,2 ”dimethoxhetane (20 ⁇ )
  • the active ingredient can be used in an appropriate dosage form according to the purpose.
  • the component is diluted with an inert liquid or solid carrier and, if necessary, mixed with a surfactant, dispersant, scavenger, etc. to form a powder, wettable powder, It can be used after being formulated into various forms such as emulsions and granules.
  • a powder can be produced by mixing and grinding an active ingredient and a solid carrier.
  • a wettable powder can be produced by mixing and grinding an active ingredient, a solid carrier, a surfactant and a dispersant.
  • Emulsions can be prepared by mixing the active ingredient, a liquid carrier, a surfactant and a dispersant.
  • Granules may be granulated by mixing an erect ingredient, a solid carrier, a surfactant, a dispersant, an auxiliary agent, or the like, or may be mixed by mixing a solid carrier, a surfactant, a dispersant, an auxiliary agent, and the like. It can be manufactured by coating the active ingredient c
  • Carriers used in these formulations include, for example, talc, bentonite, cray, kaolin, diatomaceous earth, white carbon, nomi-kiurarite, Solid carriers such as slaked lime, silica sand, ammonium sulfate, urea, etc., and liquid carriers such as i-V propizole alcohol, xylene, sicc hexoxanone, isophorone, methizolenaphthalene, etc.
  • -As surfactants and dispersants for example, alcohol monoester sulfate, alkyl aryl sulfone Acid salt, naphthalene sulfonate formalin condensate, lignosolephonate, polyoxyethylene glycol ether ether, polyoxyethylene Anorexoleately soleret, polyoxyethylene solesoltantan monofluorate, and the like can be mentioned.
  • adjuvants include lipoxymethyl cellulose, polyethylene glycol, and gum arabic.
  • the mixing ratio of the active ingredient is appropriately selected according to need, but in the case of powders and granules, it is 0.01 to 10% (weight), preferably 0.05 to 5%. (Weight), in the case of emulsions and wettable powders, 1 to 50% (weight), preferably 5 to 20% (weight), but is not limited thereto. It will not be done.
  • the compound of the present invention is applied in an amount of 0.1 g to 5 kg, preferably 1 g to 1 kg, per 10 are active ingredients.
  • the range is 0.1 to 50,000 ppm, preferably 10 to 100,000 ppm.
  • the present invention is not limited to this.
  • the compounds of the present invention may be mixed with pesticides, fungicides, other herbicides, plant growth regulators, fertilizers, and the like, if necessary.
  • Formulation Example 1 Powder One part of the compound (2) and 99 parts of diatomaceous earth are mixed and ground to obtain a powder.
  • the compound of the present invention represented by the general formula [I] can be used for various kinds of weeds which are problematic in the field, such as Asagao, Onamimi, Ooinutade, Aobu, Siroza, Perennial such as broadleaf weeds such as wildflowers, kobe, ichibi, americana chinenka, and other perennials such as horseshoe sedge, yellow sedge, kimegugu, caligrasa, kogomegalari, etc.
  • Grassicaceae Weeds, grasses, jungsongrass, hee, mehsino, enocologusa, suzumenokatabira, suzumenotetsubo, etc. It can effectively control grass weeds at low doses.
  • perennial weeds and perennials such as Tainubie, Tamagayalli, Konagi, etc., which occur in paddy fields, such as perennial weeds, Perica, Mizugayari, Krogui, Hotarui, Heramodaka etc. It exhibits excellent herbicidal effects at extremely low doses over a wide range from the germination of the weed to the growing season.
  • Test example 1 weed control by paddy soil treatment
  • Test example 2 weed removal test by upland soil treatment
  • a 100 cm 2 plastic pot is filled with field soil, and is used for edible vegetation (E'c), o-nutata (Po), ao bu (Am), and siroza. (Ch) and various seeds of Kogome gallari (Ci) were sown and covered with soil.
  • the wettable powder prepared according to Formulation Example 2 is diluted with water so that the active ingredient becomes 100 g per 100 oz.
  • 100 pieces per 100 rounds were sprayed with foliage from above the whole plant using a small sprayer. After that, the plants were grown in a greenhouse, and on the 14th day after the treatment, the herbicidal effect was investigated according to the criteria in Table 3.
  • Table 6 shows the results.
  • Test Example 4 (Test of herbicidal effect at low dose by field foliar treatment) 600 cm 2 plastic pot is filled with field soil, , Jeon Son-Grass (So), Pseudo-Nutade (Po), A-Vo (Am), Siroza (Ch), No-Asagao (Ip) and Ponata (Xa) And covered the soil. After growing for 2 weeks in a greenhouse, a predetermined amount of a wettable powder prepared according to Formulation Example 2 is diluted with water, and the mixture is added to a small atomizer at a rate of 100 ⁇ per 100 ares. Then, foliage application was performed on the whole plant from above. After that, they were raised in a greenhouse, and on the 14th day after the treatment, the herbicidal effect was investigated according to the criteria in Table 3. Table 7 shows the results.

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pyridine Compounds (AREA)

Abstract

L'invention se rapporte à un nouveau dérivé d'acide picolinique représenté par la formule générale (I), à un sel de ce dérivé, à la production de ce dérivé et à un herbicide contenant ce dérivé comme principe actif. Dans la formule (I), R représente hydrogène, alkyle, etc.; R1 et R2, qui peuvent être identiques ou différents entre eux, représentent chacun alkyle, alcoxy, etc.; X représente cyano, phénoxy, etc.; Y représente oxygène, soufre, etc.; et n est égal à 0 ou à 1. Ce dérivé et son sel possèdent un excellent pouvoir herbicide même en petites doses contre une grande variété de mauvaises herbes, de sorte qu'ils peuvent être utilisés dans des champs de plaine et de montagne, dans des terrains non cultivés et autres.
PCT/JP1991/001725 1991-12-18 1991-12-18 Derive d'acide picolinique, production de ce derive, et herbicide Ceased WO1993012109A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
PCT/JP1991/001725 WO1993012109A1 (fr) 1991-12-18 1991-12-18 Derive d'acide picolinique, production de ce derive, et herbicide
HU9201294A HU213623B (en) 1991-12-18 1991-12-18 Herbicidal compositions containing picolinic acid derivatives as active ingredients, process for producing said active ingredients and method for weed control
RO92-200527A RO109848B1 (ro) 1991-12-18 1991-12-18 Derivati de acid picolinic, procedee pentru prepararea acestora si compozitii erbicide
PL91295868A PL169374B1 (pl) 1991-12-18 1991-12-18 Srodek chwastobójczy PL
SU915011967A RU2091380C1 (ru) 1991-12-18 1991-12-18 Производные пиколиновой кислоты или их кислотно-аддитивные соли, способ их получения, нербицидная композиция и способ борьбы с сорняками
BR919106704A BR9106704A (pt) 1991-12-18 1991-12-18 Derivato de acido picolinico,metodo para sua preparacao e composicao herbicida

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/JP1991/001725 WO1993012109A1 (fr) 1991-12-18 1991-12-18 Derive d'acide picolinique, production de ce derive, et herbicide

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Publication Number Publication Date
WO1993012109A1 true WO1993012109A1 (fr) 1993-06-24

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PCT/JP1991/001725 Ceased WO1993012109A1 (fr) 1991-12-18 1991-12-18 Derive d'acide picolinique, production de ce derive, et herbicide

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BR (1) BR9106704A (fr)
HU (1) HU213623B (fr)
PL (1) PL169374B1 (fr)
RO (1) RO109848B1 (fr)
RU (1) RU2091380C1 (fr)
WO (1) WO1993012109A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9113629B2 (en) * 2013-03-15 2015-08-25 Dow Agrosciences Llc 4-amino-6-(4-substituted-phenyl)-picolinates and 6-amino-2-(4-substituted-phenyl)-pyrimidine-4-carboxylates and their use as herbicides

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6484A (en) * 1986-06-14 1989-01-05 Kumiai Chem Ind Co Ltd Picolinic acid derivative and herbicide
JPH01213202A (ja) * 1988-02-22 1989-08-28 Kumiai Chem Ind Co Ltd 除草剤組成物
JPH02121973A (ja) * 1988-09-22 1990-05-09 Basf Ag 芳香族カルボン酸誘導体および該化合物を含有する除草剤
JPH02216631A (ja) * 1988-12-09 1990-08-29 Basf Ag ピリジン誘導体及びその除草剤有効成分としての応用
JPH03106876A (ja) * 1989-08-19 1991-05-07 Basf Ag カルボン酸誘導体、該化合物を含有する除草剤および植物成長を調整する薬剤、ならびに望ましからぬ植物成長を防除する方法

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6484A (en) * 1986-06-14 1989-01-05 Kumiai Chem Ind Co Ltd Picolinic acid derivative and herbicide
JPH01213202A (ja) * 1988-02-22 1989-08-28 Kumiai Chem Ind Co Ltd 除草剤組成物
JPH02121973A (ja) * 1988-09-22 1990-05-09 Basf Ag 芳香族カルボン酸誘導体および該化合物を含有する除草剤
JPH02216631A (ja) * 1988-12-09 1990-08-29 Basf Ag ピリジン誘導体及びその除草剤有効成分としての応用
JPH03106876A (ja) * 1989-08-19 1991-05-07 Basf Ag カルボン酸誘導体、該化合物を含有する除草剤および植物成長を調整する薬剤、ならびに望ましからぬ植物成長を防除する方法

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HU213623B (en) 1997-08-28
RU2091380C1 (ru) 1997-09-27
BR9106704A (pt) 1994-03-22
HUT64321A (en) 1993-12-28
PL169374B1 (pl) 1996-07-31
HU9201294D0 (en) 1993-09-28
RO109848B1 (ro) 1995-06-30
PL295868A1 (en) 1993-10-18

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