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WO1996000723A1 - Pyridin-3-iminoalkylesters utilises comme fongicides - Google Patents

Pyridin-3-iminoalkylesters utilises comme fongicides Download PDF

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Publication number
WO1996000723A1
WO1996000723A1 PCT/EP1995/002323 EP9502323W WO9600723A1 WO 1996000723 A1 WO1996000723 A1 WO 1996000723A1 EP 9502323 W EP9502323 W EP 9502323W WO 9600723 A1 WO9600723 A1 WO 9600723A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
imino
pyridine
butyl
metal salt
Prior art date
Application number
PCT/EP1995/002323
Other languages
German (de)
English (en)
Inventor
Herbert Gayer
Peter Gerdes
Stefan Dutzmann
Klaus Stenzel
Heinz-Wilhelm Dehne
Original Assignee
Bayer Aktiengesellschaft
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 Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to EP95924246A priority Critical patent/EP0767784A1/fr
Priority to AU28834/95A priority patent/AU2883495A/en
Priority to JP8502756A priority patent/JPH10504805A/ja
Publication of WO1996000723A1 publication Critical patent/WO1996000723A1/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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • 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

Definitions

  • the present invention relates to new pyridine-3-imino-alkyl esters, a process for their preparation and their use as fungicides.
  • dichlorophenylimino-C- (isopropoxy) methyl-3-pyridine to combat fungi.
  • the effectiveness of this substance leaves something to be desired in some cases at low application rates.
  • R represents methyl, ethyl, n-propyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, dodecyl or methoxyethyl and
  • R 1 and R 2 independently of one another represent fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl or trifluoromethoxy,
  • R 1 and R 2 have the meanings given above,
  • the substances according to the invention are distinguished by a substantially better fungicidal action than the most similar in terms of constitution, compounds of the same indication known from the prior art.
  • the substances according to the invention exceed e.g. the 2 ', 4'-dichlorophenylimino-C- (isopropoxy) methyl-3-pyridine, which is a structurally obvious compound with the same direction of action, with regard to its fungicidal properties.
  • R preferably represents methyl, ethyl, n-propyl, n-butyl, sec-butyl, isobutyl, tert-butyl, the radicals of the formulas
  • R 1 preferably represents fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl or trifluoromethoxy.
  • R 2 preferably represents fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl or trifluoromethoxy.
  • Preferred substances according to the invention are also addition products of acids and those pyridine-3-iminoalkyl esters of the formula (I) in which R, R 1 and R 2 have the meanings given above as preferred.
  • the acids which can be added preferably include halohydric acids, such as, for example, hydrochloric acid and hydrobromic acid, in particular hydrochloric acid, furthermore phosphoric acid, nitric acid, sulfuric acid, mono- and bifunctional carboxylic acids and hydroxycarboxylic acids, such as acetic acid, maleic acid, Succinic acid, fumaric acid, tartaric acid, citric acid Nenoic acid, salicylic acid, sorbic acid and lactic acid as well as sulfonic acids such as p-toluenesulfonic acid, 1,5-naphthalenedisulfonic acid or camphorsulfonic acid, and also saccharin and thiosaccharin.
  • halohydric acids such as, for example, hydrochloric acid and hydrobromic acid, in particular hydrochloric acid, furthermore phosphoric acid, nitric acid, sulfuric acid, mono- and bifunctional carboxylic acids and hydroxycarboxylic acids, such as ace
  • preferred substances according to the invention are addition products from salts of metals of the II. To IV. Main group and of I. and II. And IV. To VIII. Subgroup of the periodic table of the elements and pyridine-3-imino-alkyl esters of the formula (I ), in which R, R 1 and R 2 have the meanings given above as preferred.
  • Salts of copper, zinc, manganese, magnesium, tin, iron and nickel are particularly preferred.
  • Anions of these salts are those which are derived from acids which lead to physiologically tolerable addition products.
  • Particularly preferred such acids in this connection are the hydrohalic acids, e.g. Hydrochloric acid and hydrobromic acid, also phosphoric acid, nitric acid and sulfuric acid.
  • Examples of substances according to the invention are the pyridine-3-imino-alkyl esters listed in the following table.
  • Formula (II) provides a general definition of the imino compounds required as starting materials when carrying out the process according to the invention.
  • R 1 and R 2 preferably have those meanings which have already been mentioned preferably in connection with the description of the substances of the formula (I) according to the invention for these substituents.
  • imino compounds of the formula (II) are known or can be prepared by processes which are known in principle (cf. EP-OS 0 008 145). Thus, imino compounds of the formula (II) are obtained by using nicotinamide of the formula
  • R 1 and R 2 have the meanings given above,
  • nicotinamide of the formula (IV) are known or can be prepared by methods known in principle (cf. EP-OS 0 008 145). Nicotinic acid amides of the formula (IV) are obtained by using nicotinic acid of the formula
  • R 1 and R 2 have the meanings given above,
  • Formula (III) provides a general definition of the alcohols which are further required as starting materials when carrying out the process according to the invention.
  • R preferably has those meanings which have already been mentioned preferably for this substituent in connection with the description of the substances of the formula (I) according to the invention.
  • the alcohols of the formula (III) are generally known compounds of organic chemistry.
  • Suitable diluents for carrying out the process according to the invention are all inert organic solvents which are customary for such reactions.
  • Ethers such as diethyl ether, are preferably usable.
  • Methyl tert-butyl ether ethylene glycol dimethyl ether, tetrahydrofuran and dioxane, also nitriles, such as acetonitrile, and also optionally halogenated aliphatic, cycloaliphatic and aromatic hydrocarbons, such as methylene chloride, chloroform, carbon tetrachloride, hexane, cyclohexane, benzene , Toluene, xylene and chlorobenzene.
  • nitriles such as acetonitrile
  • halogenated aliphatic, cycloaliphatic and aromatic hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, hexane, cyclohexane, benzene , Toluene, xylene and chlorobenzene.
  • Suitable acid binders for carrying out the process according to the invention are all customary inorganic or organic bases.
  • Alkali metal or alkaline earth metal hydroxides, amides, alcoholates, carbonates and hydrogen carbonates such as sodium hydroxide, potassium hydroxide, sodium amide, sodium methylate, sodium ethylate, potassium tert-butoxide, sodium carbonate, potassium carbonate, calcium carbonate, potassium hydrogen carbonate and Sodium bicarbonate, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, pyridine, N-methylpiperidine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene ( DBU).
  • DABCO diazabicyclooctane
  • DBN diazabicyclononene
  • reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between -10 ° C and 120 ° C, preferably between 0 ° C and 100 ° C.
  • the process according to the invention is generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.
  • the processing takes place according to usual methods.
  • the general procedure is to concentrate the reaction mixture
  • Water and a water-immiscible organic solvent are added to the residue, the organic phase is separated off, after drying, if appropriate, concentrated, and the remaining residue is optionally further purified by recrystallization or by chromatographic means.
  • the imino compounds of the formula (II) can be used in the form of hydrohalides or as free bases when carrying out the process according to the invention.
  • the process is carried out by suspending hydrohalides, for example hydrochlorides, of imino compounds of the formula (II) in a suitable solvent, for example chloroform, by subsequent treatment with aqueous alkali metal base, for example aqueous sodium carbonate. Solution, converted into the free bases and reacting these with alcohols of the formula (HI) or their salts (alcoholates), if appropriate in the presence of a phase transfer catalyst.
  • aqueous alkali metal base for example aqueous sodium carbonate
  • the pyridine-3-iminoalkyl esters of the formula (I) according to the invention can be converted into acid addition salts or metal salt complexes.
  • Manner according to usual salt formation methods, e.g. by dissolving a compound of formula (I) in a suitable inert solvent and adding the acid, e.g. Hydrochloric acid can be obtained and in a known manner, e.g. by filtration, isolated and, if necessary, cleaned by washing with an inert organic solvent.
  • acid e.g. Hydrochloric acid
  • Metal salt complexes can be isolated in a known manner, for example by filtering off, and optionally purified by recrystallization.
  • the active compounds according to the invention have a strong microbicidal action and can be used as fungicides.
  • Fungicides are used in crop protection to combat Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes.
  • Xanthomonas species such as Xanthomonas oryzae
  • Pseudomonas species such as Pseudomonas lachrymans
  • Erwinia species such as Erwinia amylovora
  • Pythium species such as Pythium ultimum
  • Phytophthora species such as Phytophthora infestans
  • Pseudoperonospora species such as Pseudoperonospora humuli or Pseudoperonospora cubensis;
  • Plasmopara species such as Plasmopara viticola
  • Peronospora species such as Peronospora pisi or P. brassicae
  • Erysiphe species such as Erysiphe graminis
  • Sphaerotheca species such as Sphaerotheca fuliginea
  • Podosphaera species such as Podosphaera leucotricha
  • Venturia species such as Venturia inaequalis
  • Pyrenophora species such as Pyrenophora teres or P. graminea; (Conidial form: Drechslera, Syn: Helminthosporium);
  • Cochliobolus species such as Cochliobolus sativus
  • Drechslera (Conidial form: Drechslera, Syn: Helminthosporium);
  • Uromyces species such as Uromyces appendiculatus
  • Puccinia species such as Puccinia recondita
  • Tilletia species such as Tilletia caries
  • Ustilago species such as Ustilago nuda or Ustilago avenae
  • Pellicularia species such as Pellicularia sasakii
  • Pyricularia species such as Pyricularia oryzae; Fusarium species, such as Fusarium culmorum; Botrytis species, such as Botrytis cinerea; Septoria species, such as Septoria nodorum; Leptosphaeria species, such as Leptosphaeria nodorum; Cercospora species, such as Cercospora canescens;
  • Alternaria species such as Alternaria brassicae
  • Pseudocercosporella species such as Pseudocercosporella herpotrichoides.
  • the active compounds according to the invention are particularly suitable for combating Pyricularia oryzae on rice and for combating cereal diseases, such as Leptosphaeria nodorum, Cochliobolus sativus, Pyrenophora teres and Erysiphe species.
  • the substances according to the invention show a very good action against Venturia, Uncinula, Sphaerotheca and Podosphaera.
  • the substances according to the invention can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, and ULV formulations.
  • customary formulations such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, and ULV formulations.
  • These formulations are made in a known manner, e.g. by mixing the active ingredients with
  • Extenders that is to say liquid solvents, liquefied gases and / or solid carriers under pressure, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • water e.g. organic solvents can also be used as auxiliary solvents.
  • the following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, alcohols, such as butanol or glycol, and their ethers and
  • esters ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, and water;
  • Liquefied gaseous extenders or carriers mean liquids which are at normal temperature and are gaseous under normal pressure, for example aerosol propellants, such as butane, propane, nitrogen and carbon dioxide;
  • aerosol propellants such as butane, propane, nitrogen and carbon dioxide
  • solid carriers for example natural rock powder, such as kaolins, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powder, such as highly disperse silica, aluminum oxide and silicates; as solid carriers for
  • Granules are possible: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming agents are possible: e.g. nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g.
  • Alkylaryl polyglycol ethers alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.
  • Adhesives such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide,
  • Ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to broaden the spectrum of activity or to prevent the development of resistance.
  • synergistic effects are obtained, i.e. the
  • the effectiveness of the mixture is greater than the effectiveness of the individual components.
  • Fenpropimorph fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, fluoromide, fluquinconazole, flusilazole, flusulfamide, flutolanil,
  • copper preparations such as: copper hydroxide, copper naphthenate,
  • Mancopper Mancozeb, Maneb, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metsulfovax, Myclobutanil,
  • Probenazole prochloraz, procymidone, propamocarb, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilone,
  • Cadusafos Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 157
  • Fenamiphos Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate,
  • Fipronil fluazinam, flucycloxuron, flucythrinate, flufenoxuron, flufenprox,
  • HCH heptenophos, hexaflumuron, hexythiazox, Imidacloprid, Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivemectin,
  • Methami dophos methidathione, methiocarb, methomyl, metolcarb, milbemectin, monocrotophos, moxidectin,
  • Parathion A Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet,
  • Triazophos triazuron, trichlorfon, triflumuron, trimethacarb,
  • the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, emulsifiable concentrates, emulsions, foams, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are used in the usual way, e.g. by pouring, spraying, atomizing, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients by the ultra-low-volume process or to inject the active ingredient preparation or the active ingredient itself into the soil. The seeds of the plants can also be treated.
  • the application rate can be varied over a wide range depending on the type of application.
  • the active substance concentrations in the treatment of parts of plants in the use forms are generally between 1 and 0.0001% by weight, preferably between 0.5 and 0.001%.
  • amounts of active compound of 0.001 to 50 g per kg of seed, preferably 0.01 to 10 g are generally required.
  • active ingredient concentrations of 0.00001 to 0.1% by weight, preferably 0.0001 to 0.02% are required at the site of action.
  • reaction mixture was poured onto an ice-cold solution of 193.6 g (1.4 mol) of potassium carbonate in 1.75 l of water. It is mixed with ethyl acetate and suction filtered. When the organic phase is narrowed, further solid separates, which is likewise suctioned off. 355.1 g (95% of theory) of nicotinic acid 2,4-dichloroanilide are obtained.
  • Solvent 10 parts by weight of N-methyl-pyrrolidone emulsifier: 0.6 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • the plants are sprayed with a spore suspension of Leptosphaeria nodorum.
  • the plants remain in an incubation cabin at 20 ° C. and 100% relative atmospheric humidity for 48 hours.
  • the plants are placed in a greenhouse at a temperature of approx. 15 ° C and a relative humidity of approx. 80%.
  • Evaluation is carried out 10 days after the inoculation.
  • Example 1 shows an efficiency of 100% at an application rate of 250 g / ha, while the comparison substance (A) has an efficiency of 50%.
  • Emulsifier 0.3 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • the plants are then placed in a greenhouse at 23 to 24 ° C. and at a relative atmospheric humidity of approx. 75%.
  • Evaluation is carried out 10 days after the inoculation.
  • Spray liquor has an efficiency of 60% or more, while the comparison substance (A) has an efficiency of 37%.
  • Emulsifier 0.3 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • the plants are then placed in a greenhouse at 23 ° C. and a relative atmospheric humidity of approx. 70%.
  • Evaluation is carried out 10 days after the inoculation.
  • Spray liquor has an efficiency of more than 70%, while the comparison substance has no effect.
  • Emulsifier 0.3 part by weight of alkyl aryl polyglycol ether
  • the plants are then placed in a greenhouse at 23 to 24 ° C and at a relative humidity of approx. 75%.
  • Evaluation is carried out 10 days after the inoculation.
  • Eumulsifier 0.3 part by weight of alkyl aryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • the plants are then placed in a greenhouse at 23 ° C. and a relative atmospheric humidity of approx. 70%.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (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)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pyridine Compounds (AREA)

Abstract

L'invention concerne de nouveaux pyridin-3-iminoalkylesters de la formule (I) dans laquelle R désigne méthyle, éthyle, n-propyle, n-butyle, butyle sec., isobutyle, butyle tert., pentyle, hexyle, heptyle, octyle, dodécyle ou méthoxyéthyle et R1 et R2 désignent, indépendamment l'un de l'autre, fluor, chlore, brome, méthyle, méthoxy, trifluorométhyle ou trifluorométhoxy. L'invention concerne également leurs sels d'addition d'acide et complexes de sels métalliques, un procédé permettant de préparer ces nouvelles substances et leur utilisation comme fongicides.
PCT/EP1995/002323 1994-06-29 1995-06-16 Pyridin-3-iminoalkylesters utilises comme fongicides WO1996000723A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP95924246A EP0767784A1 (fr) 1994-06-29 1995-06-16 Pyridin-3-iminoalkylesters utilises comme fongicides
AU28834/95A AU2883495A (en) 1994-06-29 1995-06-16 Pyridine-3-imino alkyl esters as fungicides
JP8502756A JPH10504805A (ja) 1994-06-29 1995-06-16 殺菌・殺カビ剤としてのピリジン−３−イミノアルキルエステル

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19944422763 DE4422763A1 (de) 1994-06-29 1994-06-29 Pyridin-3-imino-alkylester
DEP4422763.9 1994-06-29

Publications (1)

Publication Number Publication Date
WO1996000723A1 true WO1996000723A1 (fr) 1996-01-11

Family

ID=6521819

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1995/002323 WO1996000723A1 (fr) 1994-06-29 1995-06-16 Pyridin-3-iminoalkylesters utilises comme fongicides

Country Status (5)

Country Link
EP (1) EP0767784A1 (fr)
JP (1) JPH10504805A (fr)
AU (1) AU2883495A (fr)
DE (1) DE4422763A1 (fr)
WO (1) WO1996000723A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9919588D0 (en) * 1999-08-18 1999-10-20 Hoechst Schering Agrevo Gmbh Fungicidal compounds

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0008145A2 (fr) * 1978-08-08 1980-02-20 Shell Internationale Researchmaatschappij B.V. Utilisation des dérivés de la phényliminométhylpyridine comme fongicides et régulateurs de croissance des plantes, compositions qui contiennent ces dérivés, de la phényliminométhylpyridine et leur préparation

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0008145A2 (fr) * 1978-08-08 1980-02-20 Shell Internationale Researchmaatschappij B.V. Utilisation des dérivés de la phényliminométhylpyridine comme fongicides et régulateurs de croissance des plantes, compositions qui contiennent ces dérivés, de la phényliminométhylpyridine et leur préparation

Also Published As

Publication number Publication date
DE4422763A1 (de) 1996-01-04
JPH10504805A (ja) 1998-05-12
AU2883495A (en) 1996-01-25
EP0767784A1 (fr) 1997-04-16

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