WO1999012907A1 - Derives de 2,6-dichloro-4-pyridinemethanol et produits chimiques utilises en agriculture - Google Patents
Derives de 2,6-dichloro-4-pyridinemethanol et produits chimiques utilises en agriculture Download PDFInfo
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- WO1999012907A1 WO1999012907A1 PCT/JP1998/004036 JP9804036W WO9912907A1 WO 1999012907 A1 WO1999012907 A1 WO 1999012907A1 JP 9804036 W JP9804036 W JP 9804036W WO 9912907 A1 WO9912907 A1 WO 9912907A1
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- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/416—2,5-Pyrrolidine-diones 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 other ring carbon atoms
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- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
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- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
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- 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
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Definitions
- the present invention relates to a novel 2,6-dichloro-4-pyridinemethanol derivative and a pesticide containing the compound as an active ingredient, particularly a plant disease controlling agent.
- Patent No. 25144823-Japanese Patent Application Laid-Open No. 11-283720 discloses that 2,6-dioctaloisonicotinic acid derivative having a specific structure protects crops from pathogenic microorganisms It is disclosed that there is an effect. However, although these compounds had good medicinal properties, they had harm to certain crops.
- 2,6-dichloro-1-pyridinemethanol according to the present invention can be synthesized by, for example, using 2,6-dichloromouth isonicotinic acid or an ester thereof as a starting material and performing a reduction reaction.
- 2,6-dichloro-4-pyridinemethanol derivative of the present invention and the use of 2,6-dichloro-4-pyridinemethanol and the 2,6-dichloro-4-pyridinemethanol derivative as pesticides have not been known at all. .
- the problem to be solved by the present invention is to provide a new compound which is less susceptible to phytotoxicity to crops and has an excellent effect in controlling various plant diseases caused by phytopathogenic viruses, bacteria and fungi.
- An object of the present invention is to provide a pesticide, particularly a plant disease control agent, comprising dichloro-4-pyridinemethanol and / or a benzoate thereof as an active ingredient. Disclosure of the invention
- the present inventors have conducted various studies to solve this problem, and as a result, a 2,6-dichloro-4-pyridinemethanol derivative represented by the general formula (1) is used as a pesticide in a small amount, especially for controlling plant diseases.
- the present invention was found to be effective in the present invention and that there was no concern about phytotoxicity to the plant, and completed the present invention.
- W is unsubstituted or may be substituted with ⁇ an alkoxy group, an alkylthio group, a cyano group, a phenyl group, or a pyridyl group optionally substituted with a halogen atom '').
- R 1 is unsubstituted or alkenyl group, alkylthio group, phenyl group optionally substituted with alkoxy group, hydroxy group, phenylalkoxy group, phenylalkylthio group, alkyloxycarbonyl group, alkyl group A C1-C18 alkyl which may be substituted with a carbonylamino group or a phenoxy group Group, an alkenyl group having 1 to 18 carbon atoms which may be substituted with a ⁇ phenyl group optionally substituted with an alkoxy group '', ⁇ a halogen atom, 1 to 6 carbon atoms which may be substituted with a halogen atom An alkyl group, an alkoxy group having 1 to 12 carbon atoms which may be substituted with a halogen atom, an alkenyloxy group having 2 to 3 carbon atoms, a nitro group, an amino group, an alkylamino group having 1 to 4 carbon atom
- R 2 represents an alkyl group having 1 to 12 carbon atoms or a phenyl group which may be substituted with an alkyl group having 1 to 12 carbon atoms;
- R 3 represents an alkyl group having 1 to 4 carbon atoms
- R 4 represents an alkyl group having 1 to 3 carbon atoms or a phenyl group
- R 5 to R 7 each represent the same or different alkyl groups having 1 to 4 carbon atoms.
- W is - represents COR 1, wherein R 1 is unsubstituted, or "alkoxy group, an alkylthio group, an off alkylsulfonyl group which may be substituted with alkoxy groups, human Dorokishi group, Phenylalkoxy, phenylalkylthio, alkyloxycarbonyl, alkylcarbonylamino, or phenoxy group '' C1-C18 alkyl group, C1-C18 alkenyl group unsubstituted or substituted by "fuunyl group optionally substituted with alkoxy group", "halogen atom, halogen atom”
- W represents -COR '
- R 1 is an unsubstituted or alkenyl group substituted by a "phenyl group optionally substituted by an alkoxy group”.
- (E) formula (1) represents a W guard COR 1
- R 1 is, "halogen atom, a halo gen atom in an optionally substituted alkyl group having 1 to 6 carbon atoms, substituted with a halogen atom C1-C12 alkoxy group, C2-C3 alkenyloxy group, nitro group, amino group, C1-C4 alkylamino group, cyano group, acetylamino group, benzoylamino group, An acetyl group, a phenyl group or a phenoxy group, which is a phenyl group having one or more same or different substituents.
- R 2 is alkyl Le group number 1-1 2 carbon atoms, or substituted with may be phenyl group with an alkyl group with carbon number 1-1 2 2,6-dichloro-4-1-pyridine methanol derivative according to (a),
- W in the general formula (1) represents —CONHR 4 , one COOR 4 or one COCOR 4 , wherein R 4 is an alkyl group having 1 to 3 carbon atoms or a phenyl group.
- 2, 6-dichloro as an 4-pyridinemethanol derivative represents W is one S i R 5 R fi R 7 in (j) in formula (1), wherein R 5 to R 7 are the same or different and each A 2,6-dichloro-1-4-pyridinemethanol derivative according to (a), which is an alkyl group having 1 to 4 carbon atoms;
- the substituted or unsubstituted alkyl group having a predetermined number of carbon atoms represented by W and R ′ to R 7 of the above is selected from linear, branched or cyclic alkyl groups, for example, methyl, ethyl, n —Propynole, isopropynole, n-butynole, isobutynole, 2-butyl, tert-butynole, n-pentynole, n-hexynole, n-octynole, 2-ethynolehexyl, n-dodecyl, n-octactadecyl, n —Eicosyl, cyclopropyl, cyclopentinole, cyclohexinole, methoxymethinole, methoxetine, butoxybutyl, methoxypentyl, dodecyloxhetyl
- alkenyl group which may be substituted with an alkoxy group or a phenyl group represented by R ′
- R ′ examples include, for example, ethenyl, propenyl, butenyl, pentenyl, hexeninole, heptadeceninole, butageninole, and pentagen. Ninore, heptadecane ninole, feninoleetininole, feninoleproteninole, methoxypheninoleeteninole, and the like.
- Examples of the phenyl group having one or more same or different predetermined substituents represented by R 1 include, for example, fluorophenyl, chlorophenyl, bromophenyl, methinorefeninole, hexinolefeninole, and trifluoronoreminolefe Ninole, Chloromethinolephenyl, Methoxyphenole, Hexinoleoxyphenyl, Dodecyloxyphene, Cyclohexenoleoxyphene, Diphnoleolomethoxyphene, Triflenore Ethoxyphene, Propeinoleoxyphene Examples include nitrophenyl, aminophenyl, N, N'-dimethylaminophenyl, cyanophenyl, acetylaminophenyl, benzoylaminophenyl, acetyloxyphenyl, biphenyl, phenoxyphenyl and the like.
- a 5- to 6-membered heterocyclic residue which may be substituted with an alkyl group having 1 to 4 carbon atoms represented by R 1 and which contains one nitrogen atom, oxygen atom or sulfur atom as a ring-constituting atom Examples thereof include furyl, cyenyl, pyrrolyl, bilanyl, pyridinyl, methylpyridyl and the like.
- Examples of the phenyl group which may be substituted with an alkyl group having 1 to 12 carbon atoms represented by R 2 include methylphenyl, hexylphenyl, dodecylphenyl and the like.
- Tables 1 to 10 As shown in Table 1, 2,6-dichro-l4-pyridinemethanol in Table 1 and 2,6-dichro-l-l-4l-pyridinemethanol benzoate in Table 5 are known compounds. It is a new compound.
- H2 H H- H2) 4 One CH 2 CH (CH 3 ) 2
- the compound represented by the general formula (1) of the present invention can be produced by a general method used for producing an ether or an ester.
- the following reaction formulas (2) to (4) ) the production method of the compound of the present invention is not limited to this production method.
- W and R 1 in the reaction formulas (2) to (4) have the same meanings as defined in the formula of the general formula (1)
- R H represents an alkyl group having 1 to 4 carbon atoms
- L represents Represents a hydroxyl group or a halogen atom
- M represents hydrogen or a metal atom (sodium, potassium, cesium, etc.).
- 2,6-dichloro-1-pyridinemethanol or its alcohol is dissolved in an appropriate solvent, if necessary, in the presence of a dehydrating agent, an acid or a base, to obtain an alkyl halide derivative, carboxylic acid derivative, or carboxylic acid.
- a dehydrating agent an acid or a base
- an acid chloride derivative a sulfonic acid chloride derivative, a phosphoryl chloride derivative, a halogenated formic acid derivative or a halogenated silane derivative
- the 2,6-dichloromethane derivative represented by the formula (1) is obtained.
- a pyridine methanol derivative can be obtained.
- 2,6-dichloro-4-pyridinemethanol is used as a suitable halogenating agent or After forming a leaving group by reacting with an aryl sulfonic acid or the like, it is reacted with a carboxylic acid derivative, an alcohol derivative, or the like to form a 2,6-dichloro-4-pyridinepyridine derivative represented by the formula (1). Can be obtained.
- the compound represented by the general formula (1) can be obtained by adding 2,6-dichloro-4-pyridinemethanol to an olefin derivative or an isocyanate derivative in the presence of a catalyst such as an acid or a base.
- reaction solvent examples include hydrocarbons such as hexane, benzene, and toluene; phenolic alcohols such as methanol and ethanol; polyhydric alcohols and esters such as ethylene glycol, ethylene glycol monoethyl ether; getyl ether; Ethers such as drofuran, halogenated hydrocarbons such as chloroform and dichloroethane, and non-protonic polar solvents such as N, N-dimethylformamide and dimethylsulfoxide can be used.
- hydrocarbons such as hexane, benzene, and toluene
- phenolic alcohols such as methanol and ethanol
- polyhydric alcohols and esters such as ethylene glycol, ethylene glycol monoethyl ether
- getyl ether Ethers such as drofuran, halogenated hydrocarbons such as chloroform and dichloroethane, and non-protonic polar solvents
- the base examples include organic bases such as triethylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, and diazabisicopendene, hydroxides such as sodium hydroxide and hydroxylated lime, lithium carbonate, and cesium carbonate. Can be used.
- the reaction temperature varies depending on the solvent, base and the like, but is usually in the range of -10 ° C to the boiling point.
- the reaction time varies depending on the reaction temperature, solvent, base and the like, but is usually 0.1 to 10 hours, preferably 0.5 to 5 hours.
- the 2,6-dichloro-41-pyridine methanol as a raw material for synthesizing the compound of the present invention is described in, for example, J. Prakt. Chem., 134, 177-187 (1. 932) describes the synthesis method.
- the novel compound of the present invention is a compound of the general formula (1) wherein W is unsubstituted or substituted by "a pyridyl group optionally substituted with an alkoxy group, an alkylthio group, a cyano group, a phenyl group, or a halogen atom".
- a 2,6-dichloro-4-pyridinemethanol derivative which is an alkyl group having 1 to 8 carbon atoms or a trifluoromethylpyridyl group
- —W in general formula (1) represents —S0 2 R 2 , wherein R 2 is an alkyl group having 1 to 12 carbon atoms or a phenyl group that may be substituted with an alkyl group having 1 to 12 carbon atoms.
- 2,6-dichloro-4-pyridine-methanol derivatives 2,6-dichloro-4-pyridine-methanol derivatives,
- —W in the general formula (1) represents —PO (OR 3 ), and R : i is an alkyl group having 1 to 4 carbon atoms.
- W represents one CONHR 4 , one COOR 4 or —COCOR 4 , wherein R 4 is an alkyl or phenyl group having 1 to 3 carbon atoms.
- W represents one Si R 5 R H R 7 , wherein R 5 to R 7 are the same or different alkyl groups having 1 to 4 carbon atoms, 2,6-dichloro-4. -Includes bilidinmethanol derivatives. Among these, from the viewpoint of the balance between pesticide activity and phytotoxicity, W in the general formula (1) may be unsubstituted or may be substituted with an alkoxy group, an alkylthio group, a cyano group, a phenyl group, or a halogen atom.
- a 2,6-dichloro-41-pyridinemethanol derivative which is an alkyl group having 1 to 8 carbon atoms or a trifluoromethylpyridyl group substituted with a "pyridyl group" is preferable.
- W is - COR 1 represents, wherein R 1 is unsubstituted, or "alkoxy group, an alkylthio group, may be substituted with an alkoxy group phenyl Group, a hydroxy group, a phenylalkoxy group, a phenylalkylthio group, an alkyloxycarbonyl group, an alkylcarbonylamino group, or a phenoxy group, an alkyl group having 1 to 18 carbon atoms,
- a halogen atom an alkyl group having 1 to 6 carbon atoms which may be substituted with a halogen atom, an alkoxy group having 1 to 12 carbon atoms which may be substituted with a halogen atom, an alkenyloxy group having 2 to 3 carbon atoms, Nitro group, amino group, alkylamino group having 1 to 4 carbon atoms, cyano group, acetylamino group, benzoylamino group, acetyloxy group, phenyl Or a phenyl group having one or more identical or different substituents selected from the group consisting of
- R ′ is an unsubstituted or an alkenyl group substituted with a “fuunyl group optionally substituted with an alkoxy group” 2,6 —Dichloro-4-pyridinemethanol derivative, or R 1 is a “haguchigen atom, an alkyl group having 1 to 6 carbon atoms which may be substituted by a hahagen atom, or a carbon atom which may be substituted by a halogen atom.
- a 2,6-dichloro-41-pyridinemethanol derivative which is a phenyl group having at least one same or different substituent (s) selected from the group: Among them, more preferably, a 2,6-dichloro-1-41-pyridine methanol derivative in which R ′ is an alkoxyphenyl group having 1 to 12 carbon atoms which may be substituted with a halogen atom.
- the pesticides are various plant diseases caused by phytopathogenic viruses, bacteria and fungi, for example, the main diseases of rice. Although it can be applied to blast and spot disease of cucumber, it is particularly effective for blast. It is considered that this drug exerts not only a direct bactericidal action against plant pathogens, but also a disease control effect by eliciting a resistance reaction against plant pathogens inherent in plants.
- the 2,6-dichro-141-pyridinemethanol derivative of the present invention can be used alone, but known solid and liquid carriers and dispersants usually used in the preparation of agricultural chemicals are usually used.
- auxiliary agents such as diluents, emulsifiers, spreading agents, and thickeners
- they can be formulated and used in the form of wettable powders, liquids, oils, powders, granules, sols (flowables) and the like.
- Solid and liquid carriers include, for example, talc, clay, bentonite, kaolin, diatomaceous earth, montmorillonite, mica, vermiculite, gypsum, calcium carbonate, white carbon, wood flour, starch, alumina, silicate, sugar weight Coalescing, waxes, water, alcohols (methyl alcohol, ethyl alcohol, n -propynoleanol, isopropyl alcohol, n-butyl alcohol, ethylene glycol, benzyl alcohol, etc.), petroleum fractions (petroleum ether, Kerosene, solvent naphtha, etc.), aliphatic or alicyclic hydrocarbons (n-hexane, cyclohexane, etc.), aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, chlorobenzene, benzene , Methyl naphthalene, etc.), halogenated carbon Hydro
- auxiliary agents include nonionic surfactant surfactants (polyoxyethylene alkyl ether, polyoxyethylene anolequinole ester, polyoxyethylene alkyl phenyl ether, polyoxyethylene sonolebitan alkyl ester, sonolebitan alkyl Ester, etc.), anionic surfactants
- raw materials alkylbenzenesulfonate, alkylsulfosuccinate, polyoxyethylene alkylsulfate, arylsulfonate, etc.
- cationic surfactants alkylamines) , Polyoxyethylene alkylamines, quaternary ammonium salts, etc.
- amphoteric surfactant IJ alkylaminoethylglycine, alkyldimethylbetaine, etc.
- poly vinyl alcohol
- hydroxypropinoresenorelose canoleboxymethinoresenorelose
- the present agent can be used in combination with various agricultural or horticultural fungicides, herbicides, plant growth regulators, pesticides such as insecticides, acaricides, and fertilizers.
- the active ingredient content of this drug varies depending on the form of preparation, application method and other conditions, but is usually 0.5 to 95% (weight), preferably 1 to 50% (weight).
- the method of application of this chemical can be applied to plants (foliage application), application to plant growing soil (soil application), application to paddy water (water application), application to seeds (seed treatment), etc. It is.
- the application rate of this drug varies depending on the plant and disease to be applied, but in the case of foliar application, a solution with an active ingredient concentration of l to 100 ppm, preferably 100 to 100 ppm Is preferably applied in an amount of 50 to 300 L per 10 ares, and in the case of soil application and water surface application, 0.1 to 100 g, particularly preferably 1 to 100 g per 10 ares as an active ingredient. It is preferred to apply from 0 to 100 g. In the case of seed treatment, 0.001 to 50 g of the active ingredient is preferably applied to 1 kg of the seed.
- the 2,6-dichloro-1-pyridinemethanol derivative according to the present invention has no fear of phytotoxicity to plants, is useful as a plant disease control agent, and is useful for various plant diseases caused by phytopathogenic viruses, bacteria and fungi. It has an excellent effect on controlling pests.
- Mass storage 230, 232, 16 1, 1 63
- Example 6 1.4 g of 2,6-dichloro-1-4-methanol was dissolved in 5 ml of pyridine and cooled with ice. To this was added dropwise 1.5 g of 2-nitrobenzoyl chloride prepared from 2-nitrobenzoic acid and thionyl chloride. After the reaction solution was stirred at room temperature for 2 hours, dichloromethane was added, the organic layer was washed with water, and sodium sulfate was added and dried. The solvent was distilled off, and the residue was purified by silica gel column chromatography to obtain 1.4 g of 2- (2-to-)-benzoic acid (2,6-dichloro-4-pyridinyl) methyl ester (Compound No. 69). .
- Example 9 0.35 g of 2,6-dichloro-4-monochloromethylpyridine, 0.31 g of benzoylformic acid and 0.19 g of sodium hydrogen carbonate are added to 5.Oml of dimethylformamide, and the mixture is added at 70 ° C for 4 hours. The mixture was heated and stirred. After cooling, ethyl acetate was added to the reaction solution, the organic layer was washed with water, and sodium sulfate was added and dried. The solvent was distilled off, and the residue was purified by silica gel column chromatography to obtain 0.18 g of benzoylformic acid (2,6-dichloromouth 4-pyridinyl) methyl ester (Compound No. 95).
- a two-leaf rice plant (variety: Asahi Aichi) bred in a pot (diameter 6 cm, height 5.5 cm) was diluted with water from each of the wettable powders described in (Formulation Example 2) to give a drug solution. Soil applied (0.1 mg of active ingredient in pot). 14 days later, a spore suspension of rice blast fungus (Py ricularia oryzae) was sprayed and inoculated, left in a humidity chamber at 25 ° C for 24 hours, and then allowed to develop disease in a greenhouse. The plaque count was investigated.
- probenazole granule 1J active ingredient 8%
- 2,6-dichloromouth isonicotinic acid compound described in Patent No. 2514823
- the test was carried out in the same manner with the same amount of active ingredient.
- the control value was calculated by the following formula.
- phytotoxicity leaf withering, plants Growth inhibition was observed. The results are shown in Table 28. In the table, a minus (1) indicates that no phytotoxicity occurred, and a plus (+) indicates that phytotoxicity occurred.
- Control value (%) [(number of lesions in untreated area / number of lesions in treated area) Z number of lesions in untreated area] X 100
- the present invention comprises a novel 26-dicro41-pyridinemethanol derivative, an agrochemical containing the compound as an active ingredient, and 26-diclo41-pyridinemethanol and Z or a benzoate thereof as an active ingredient. It is possible to provide a plant disease control agent, especially a rice blast control agent, which has no effect on pesticides, especially on plant bodies, and has a sufficient effect.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE69831085T DE69831085D1 (de) | 1997-09-10 | 1998-09-09 | 2,6-dichlor-4-pyridinmethanolderivate als chemikalien für die landwirtschaft |
AU90001/98A AU736746B2 (en) | 1997-09-10 | 1998-09-09 | 2,6-dichloro-4-pyridinemethanol derivatives and agricultural chemicals |
KR1020007002382A KR20010023728A (ko) | 1997-09-10 | 1998-09-09 | 2,6-디클로로-4-피리딘메탄올 유도체 및 이를 포함하는 농약 |
US09/508,261 US6281231B1 (en) | 1997-09-10 | 1998-09-09 | 2,6-dichloro-4-pyridinemethanol derivatives and agricultural chemicals |
EP98941775A EP1016661B1 (en) | 1997-09-10 | 1998-09-09 | 2,6-dichloro-4-pyridinemethanol derivatives as agricultural chemicals |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP9/245279 | 1997-09-10 | ||
JP24528097 | 1997-09-10 | ||
JP9/245280 | 1997-09-10 | ||
JP24527997 | 1997-09-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1999012907A1 true WO1999012907A1 (fr) | 1999-03-18 |
Family
ID=26537146
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP1998/004036 WO1999012907A1 (fr) | 1997-09-10 | 1998-09-09 | Derives de 2,6-dichloro-4-pyridinemethanol et produits chimiques utilises en agriculture |
Country Status (9)
Country | Link |
---|---|
US (1) | US6281231B1 (ja) |
EP (1) | EP1016661B1 (ja) |
KR (1) | KR20010023728A (ja) |
CN (1) | CN1120155C (ja) |
AU (1) | AU736746B2 (ja) |
DE (1) | DE69831085D1 (ja) |
ID (1) | ID23777A (ja) |
TW (1) | TW490287B (ja) |
WO (1) | WO1999012907A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2014065209A1 (ja) * | 2012-10-23 | 2014-05-01 | 日本曹達株式会社 | ピリジン化合物またはその塩、有害生物防除剤、殺虫剤または殺ダニ剤、および外部寄生虫防除剤 |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10063114A1 (de) * | 2000-12-18 | 2002-06-20 | Bayer Ag | Dichlorpyridylmethylcyanamidine |
DE10063486A1 (de) * | 2000-12-20 | 2002-07-04 | Bayer Ag | Dichlorpyridylmethylamide |
EP2768906B1 (en) | 2011-10-18 | 2019-02-27 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Fluorescent dyes with phosphorylated hydroxymethyl groups and their use in light microscopy and imaging techniques |
CA3056563C (en) * | 2017-03-17 | 2023-03-14 | Meiji Seika Pharma Co., Ltd. | Plant disease control agent |
CN114190189A (zh) * | 2021-11-18 | 2022-03-18 | 山东元泰生物工程有限公司 | 一种能够促进植物生长的方法 |
Citations (2)
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JPS62277361A (ja) * | 1986-05-16 | 1987-12-02 | ロ−ヌ−プ−ラン・アグロシミ | ニコチン酸誘導体をベ−スとする殺菌組成物、新規なニコチン酸誘導体及びその製法 |
WO1997020840A1 (de) * | 1995-12-07 | 1997-06-12 | Bayer Aktiengesellschaft | 1,2,3-thiadiazolcarbonsäure(thio)ester und ihre verwendung als schädlingsbekämpfungsmittel oder als mikrobizide |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1059990A (en) * | 1964-12-18 | 1967-02-22 | Ici Ltd | Substituted pyridines |
DE3615293A1 (de) * | 1986-05-06 | 1987-11-12 | Bayer Ag | Verwendung von heteroarylethylaminen zur leistungsfoerderung bei tieren, heteroarylethylamine und verfahren zu ihrer herstellung |
IL83978A (en) | 1986-09-26 | 1992-05-25 | Ciba Geigy | Process and compositions containing dihalopyridine derivatives for protecting plants against diseases,certain such novel derivatives and their preparation |
EP0334813B1 (de) * | 1988-03-25 | 1994-02-02 | Ciba-Geigy Ag | Mittel zum Schutz von Pflanzen gegen Krankheiten |
US5501788A (en) | 1994-06-27 | 1996-03-26 | Conoco Inc. | Self-stabilizing pitch for carbon fiber manufacture |
WO1996037472A2 (en) | 1995-05-24 | 1996-11-28 | Novartis Ag | Pyridine-microbicides |
MY132496A (en) | 1998-05-11 | 2007-10-31 | Vertex Pharma | Inhibitors of p38 |
-
1998
- 1998-09-09 WO PCT/JP1998/004036 patent/WO1999012907A1/ja not_active Application Discontinuation
- 1998-09-09 KR KR1020007002382A patent/KR20010023728A/ko not_active Application Discontinuation
- 1998-09-09 DE DE69831085T patent/DE69831085D1/de not_active Expired - Lifetime
- 1998-09-09 ID IDW20000467A patent/ID23777A/id unknown
- 1998-09-09 EP EP98941775A patent/EP1016661B1/en not_active Expired - Lifetime
- 1998-09-09 CN CN98809039A patent/CN1120155C/zh not_active Expired - Fee Related
- 1998-09-09 AU AU90001/98A patent/AU736746B2/en not_active Ceased
- 1998-09-09 US US09/508,261 patent/US6281231B1/en not_active Expired - Fee Related
- 1998-09-10 TW TW087115080A patent/TW490287B/zh not_active IP Right Cessation
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS62277361A (ja) * | 1986-05-16 | 1987-12-02 | ロ−ヌ−プ−ラン・アグロシミ | ニコチン酸誘導体をベ−スとする殺菌組成物、新規なニコチン酸誘導体及びその製法 |
WO1997020840A1 (de) * | 1995-12-07 | 1997-06-12 | Bayer Aktiengesellschaft | 1,2,3-thiadiazolcarbonsäure(thio)ester und ihre verwendung als schädlingsbekämpfungsmittel oder als mikrobizide |
Non-Patent Citations (1)
Title |
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See also references of EP1016661A4 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2014065209A1 (ja) * | 2012-10-23 | 2014-05-01 | 日本曹達株式会社 | ピリジン化合物またはその塩、有害生物防除剤、殺虫剤または殺ダニ剤、および外部寄生虫防除剤 |
Also Published As
Publication number | Publication date |
---|---|
CN1120155C (zh) | 2003-09-03 |
DE69831085D1 (de) | 2005-09-08 |
KR20010023728A (ko) | 2001-03-26 |
CN1270581A (zh) | 2000-10-18 |
EP1016661A1 (en) | 2000-07-05 |
EP1016661A4 (en) | 2001-05-16 |
ID23777A (id) | 2000-05-11 |
AU736746B2 (en) | 2001-08-02 |
US6281231B1 (en) | 2001-08-28 |
TW490287B (en) | 2002-06-11 |
AU9000198A (en) | 1999-03-29 |
EP1016661B1 (en) | 2005-08-03 |
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