WO1994023576A1 - UTILISATION DE DERIVES DE L'ACIDE 7-ETHYNYL α-(METHOXYMETHYLENE) 1-NAPHTALENE ACETIQUE POUR LA PREPARATION DE COMPOSITIONS FONGICIDES - Google Patents
UTILISATION DE DERIVES DE L'ACIDE 7-ETHYNYL α-(METHOXYMETHYLENE) 1-NAPHTALENE ACETIQUE POUR LA PREPARATION DE COMPOSITIONS FONGICIDES Download PDFInfo
- Publication number
- WO1994023576A1 WO1994023576A1 PCT/FR1994/000417 FR9400417W WO9423576A1 WO 1994023576 A1 WO1994023576 A1 WO 1994023576A1 FR 9400417 W FR9400417 W FR 9400417W WO 9423576 A1 WO9423576 A1 WO 9423576A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- radical
- carbon atoms
- compounds
- methoxymethylene
- alkyl
- Prior art date
Links
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- 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
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
-
- 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 the use of derivatives of acid 7-ethynyl ⁇ - (methoxymethylene) 1-naphthalene acquit ⁇ that for the preparation of fungicidal compositions.
- a hydrogen or halogen atom - an alkyl radical containing up to 8 linear, branched or cyclic saturated or unsaturated carbon atoms, optionally substituted by one or more hydroxyl radicals, by one or more atoms of halogen, optionally interrupted by one or more heteroatoms chosen from oxygen, nitrogen or sulfur atoms,
- R ' 1 and R' 2 identical or different represent a hydrogen atom, a linear or branched alkyl radical, containing up to 4 carbon atoms, - an aryl or aryloxy radical containing up to 18 carbon atoms optionally substituted on the aryl ring by one- or more substituents chosen from halogen atoms, the radical N0 2 , the radical C ⁇ N, the alkyl, O-alkyl and S-alkyl radicals, linear, branched or cyclic, saturated or unsaturated, containing up to 8 carbon atoms, optionally substituted by one or more halogen atoms, the aryl or aryloxy radicals containing up to 16 carbon atoms, optionally substituted by one or more halogen atoms and the radical
- R "- ⁇ and R" identical or different from each other, represent a hydrogen atom, an alkyl radical containing up to 4 carbon atoms or an aryl radical containing up to 18 atoms carbon, optionally substituted by one or more halogen atoms,
- heterocyclic 5 or 6-membered aryl radical containing 1, 2 or 3 heteroatoms chosen from oxygen, sulfur and nitrogen atoms, optionally substituted by one or more radicals chosen from the group consisting of hydroxyl radicals, N0 2 , C ⁇ N, halogen atoms, alkyl, O-alkyl and S-alkyl radicals, containing up to 8 carbon atoms, linear, branched or cyclic optionally substituted by one or more halogen atoms, by one or more hydroxyl radicals and the radicals
- Ra, Rb and Rc in which Ra, Rb and Rc, identical or different, represent a linear, branched or cyclic alkyl radical containing up to 4 carbon atoms, optionally substituted by one or more halogen atoms, an aryl radical optionally substituted by one or more halogen atoms, one or more hydroxyl radicals, one or more alkyl radicals, linear or branched, optionally substituted by one or more halogen atoms, 'one or more O-alkyl or S radicals -alkyl containing up to 8 carbon atoms, optionally substituted by one or more halogen atoms, ab ⁇ / or R represents a radical -CR 'in which a and b, identical or different, represent a hydrogen atom, a halogen atom, a hydroxyl radical, a linear or branched alkyl radical containing up to 6 carbon atoms optionally substituted by one or more halogen atoms or a linear or
- halogen atoms or by a radical, in which Ra, Rb and Rc have the meanings indicated above, for the manufacture of fungicidal compositions.
- - alkyl preferably represents a methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl radical,
- - cycloalkyl preferably represents cyclopropyl, cyclobutyl, cyclopentyl, - unsaturated alkyl preferably represents ethenyl, ethyl, propenyl, propynyl, butenyl, butynyl,
- - aryl preferably represents the phenyl radical
- heterocyclic aryl preferably represents a thiazolyl, oxazolyl, isothiazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl (1,2,4) or (1,3,4), triazolyl, imidazolyl, pyridynyl, pyrimidynyl or pyrazolyl radical,
- R or R ' represents a halogen, it is preferably a bromine or chlorine atom
- R or R ' represents a radical itself substituted by a halogen atom
- the halogen is preferably a fluorine, chlorine or bromine atom.
- the invention more particularly relates to the use of the compounds of formula (I) in which the radical R 2 represents a methyl radical as well as the use of those in which R 3 represents a methyl radical, for the manufacture of fungicidal compositions.
- the geometry of the exo double bond (enol ether) is E or Z and the invention which relates to the use of the products E and of the products Z, as well as mixtures E + Z, has more specifically for object l use of the compounds in which the geometry of the exo double bond (enol ether) is E.
- R represents a radical alkyl containing up to 6 carbon atoms and very particularly the use of the compounds of formula (I) in which R represents an isopropyl radical, as well as those in which R represents a terbutyl radical, mention may also be made of the use of compounds of formula (I) in which R represents an ab -CR 'radical in which a and b which are identical or different represent a hydrogen atom, a hydroxyl radical, a linear or branched alkyl radical containing up to 4 atoms carbon or a and b form together with the atom of carbon to which they are linked a cycloalkyl radical containing up to 4 carbon atoms and R 'has the significance indicated above and in particular the use of compounds of formula (I) in which R represents a radical:
- R represents a hydrogen atom, a phenyl radical, a trimethyl silyl radical or a pyridinyl radical.
- the invention particularly relates to the use of the compounds of formula (I), the preparation of which is set out below and very particularly the compounds of preparations 1, 7 and 10 or even that of the compounds of preparations 2, 4 , 5, 8, 13 and 24 for the manufacture of fungicidal compositions.
- a more particular subject of the invention is the use of the compounds of formula (I) as defined above for the manufacture of fungicidal compositions containing from 0.001 to 1% by weight of compounds of formula (I).
- the compounds of formula (I) exhibit excellent fungicidal activity. They make it possible to fight against the mushrooms which have already penetrated inside the plant tissues. Which is particularly interesting in the case where it is no longer possible to control diseases caused by fungi once contamination has already occurred.
- the activity spectrum of the compounds of formula (I) covers a large number of phytopathogenic fungi of various economic importance, for example Pyricularia cryzae, Venturia inaequalis, Cercospora beticola, Erysiphica- ceae (Sp.
- Powdery mildew Fusarium- , Drechslera- and Leptosphaeria-, Plasmopara viticola, Phytophtora infestans, Pseudoperonospora cubensis, various rusts, strains of Botrylis cinerea sensitive and resistant to BCM- and / or Dicarboximide-, Sclerotinia solerotioru, strains of Pseudocercosporella herpotrich Pellicularia sasakii.
- the compounds of the invention can also be used in different industrial sectors, for example to protect wood or as a preservative for paints.
- compositions which contain, in addition to the compounds of formula (I), suitable formulating agents and the invention particularly relates to fungicidal compositions containing from 0.001 to 1% by weight of compounds of formula ( I).
- the possible formulations vary according to biological and physicochemical parameters. They can be, for example, wettable powders, emulsifiable concentrates, aqueous solutions, emulsions, spray solutions, dispersions in oil or in water, suspoemulsions, powders, treatment of seeds, of granules for example of microgranules, of granules to be sprayed, of granules coated, of absorption granules, of granules dispersible in water, of ULV formulation, of microcapsules, of waxes or of baits.
- Combinations with other active ingredients such as pesticides, fertilizers and / or growth regulators can be prepared on the basis of these formulations, it can be a ready-to-use mixture or a tank mixture .
- Wettable powders are preparations which can be dispersed uniformly in water and contain, in addition to the active substance, other wetting agents, such as polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, alkylsulfonates or alkylphenosulfonates and dispersing agents.
- other wetting agents such as polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, alkylsulfonates or alkylphenosulfonates and dispersing agents.
- other wetting agents such as polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, alkylsulfonates or alkylphenosulfonates and dispersing agents.
- the active ingredient is dissolved with an organic solvent such as methanol, butanol, cyclohexanone, dimethylformamide, xylene, or other aromatic compounds or other boiling point hydrocarbons more high with additionally one or more emulsifying agents.
- organic solvent such as methanol, butanol, cyclohexanone, dimethylformamide, xylene, or other aromatic compounds or other boiling point hydrocarbons more high with additionally one or more emulsifying agents.
- emulsifying agents examples include calcium salts of arylalkylsulfonic acid, such as calcium dodecylbenzenesulfonate, or non-ionic emulsifiers such as fatty acid polyglycol esters, alkylarylpolyglycol ethers, polyglycol ethers, fatty acid esters of propylene oxide and ethylene oxide , polyoxyethylene fatty acid esters, or polyoxyethylene esters.
- arylalkylsulfonic acid such as calcium dodecylbenzenesulfonate
- non-ionic emulsifiers such as fatty acid polyglycol esters, alkylarylpolyglycol ethers, polyglycol ethers, fatty acid esters of propylene oxide and ethylene oxide , polyoxyethylene fatty acid esters, or polyoxyethylene esters.
- the active ingredient can be ground with finely divided substances such as talc or natural clays such as kaolin, bentonite, pyrophylite or diatomaceous earth.
- finely divided substances such as talc or natural clays such as kaolin, bentonite, pyrophylite or diatomaceous earth.
- ligands such as polyvinyl alcohols, sodium polyacrylates, or mineral oils.
- the concentration of active principle is for example from 10 to 90% by weight, the remainder being constituted by conventional ingredients of formulation. In the case of emulsifiable concentrates, the concentration of active principle is approximately 5 to 80% by weight.
- the formulations in powder form usually contain from 5 to 20% by weight of active principle, the solutions for spray from 2 to 20% by weight approximately.
- the concentration of active principle varies according to whether the active principle is liquid or solid and according to the auxiliary substances of formulation used.
- compositions optionally contain adhesives, wetting agents, dispersants, emulsifiers, penetrating agents, solvents, fillers and vehicles.
- adhesives wetting agents, dispersants, emulsifiers, penetrating agents, solvents, fillers and vehicles.
- commercially available concentrates are usually diluted with water in the case of wettable powders, emulsifiable concentrates, dispersants and sometimes microgranules.
- the preparations in the form of powders or granules and the solutions for sprays are generally not diluted with other substances before use.
- the amount of active ingredient to be applied varies with external conditions such as temperature and humidity. It can vary within wide limits, for example between 0.005 and 10.0 kg / ha or more, but preferably from 0.01 to 5 kg / ha.
- the compounds of formula (I) can be used either alone or in combination with other fungicides.
- fungicides which can be used include the following products:
- the compounds of the invention can also be formulated with other active ingredients, such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth regulators or herbicides.
- active ingredients such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth regulators or herbicides.
- insecticides mention may be made of phosphoric esters, carbamates, carboxylic esters, forma idines, tin derivatives and substances prepared by fermentation.
- phosphoric esters there may be mentioned: Acephate, Azamethiphos, Azinphos-ethyl, Azinphos-methyl, Bromophos, Bromophos-ethyl, Chlorfenvinphos, Chlormephos, Chlorpyrifos, Chlorpyrifos-ethyl, Demeton, Demeton-S- methyl, Demeton-S -methyl sulphone, Dialifos, Diazinon, Dichlorvos, Dicrotophos, 0,0-1,2,2,2-tetrachlorethylphosphorothioate (SD 208 304), Dimethoate, Disulfoton, EPN, Ethion, Ethoprophos, Etrimfos, Famphur, Fena iphos, Fenitriothion, Fensulfothion, Fenthion, Fonofos, For othion, Heptonophos, Isozophos, Is, Is
- carbamates there may be mentioned: Aldicarb, 2-sec-butylphenylmethylcarbamate (BPMC), Carbaryl, Carbofuran, Carbosulfan, Cloathocarb, Benfuracarb, Ethiofen- carb, Furathiocarb, Isoprocarb, Methomyl, 5-methyl-m-cumenyl- butyryl (methyl) carbamate, Oxamyl, Pirimicarb, Propoxur, Thio- dicarb, Thifanos, 4,9 -triaza-4-benzyl-6,10-dimethyl- 8-oxa7-oxo-5, ll-dithia-9-dodecenoate (OK 135), 1-methylthio (ethylidene-amino) N-methyl N- (morpholinothio) carbamate (UC 51717).
- BPMC 2-sec-butylphenylmethylcarbamate
- BPMC 2-sec-butylpheny
- carboxylic esters mention may be made of: Allethrine, Alphametrine, 5-Benzyl 3-furylmethyl (E) - (1R) -cis 2,2-dimethyl 3- (2-oxothiolan 3-ylidenemethyl) cyclopropane-carboxylate, Biolallethrine , (S) Bioallethrine, Bioresmethrine, Biphenate, (RS) -l-cyano l- (6-phenoxy 2-pyridyl) methyl (1RS) trans-3- (4-tert-butylphenyl) 2,2-dimethylcyclopropanecarboxylate ( NCI 85193), Cycloprothrine, Cyhalothrine, Cypermethrine, Cyphenothrine, Deltamethrine, Empenthrine, Esfenvalerate, Fenfluthrine, Fenpropathrine, Fenvalerate, Flucythrinate, Flumethrine, Fluvalinate (D-isomer), Permethrine, Ph
- amidine there may be mentioned: Amitraz, Chlordimeform.
- tin compounds include: Cyhexatin and Fenbutatinoxide.
- tin compounds include: Cyhexatin and Fenbutatinoxide.
- a powder is prepared by mixing 10 parts by weight of active material with 90 parts by weight of talc and mixing the whole in a mortar.
- a wettable powder easily dispersible in water is prepared by mixing 25 parts by weight of active material, 65 parts by weight of quartz containing koalin as inert material, 10 parts by weight of potassium ligninsulfonate and 1 part by weight of sodium oleoylmethyl taurinate as a wetting and dispersing agent and by molding the mixture in a needle disc mill.
- a dispersion concentrate that is easily dispersible in water is prepared by mixing 40 parts by weight of active substance, 7 parts by weight of monoestersulfosuccinic, 2 parts by weight of sodium salt of ligninsulfonic acid, 51 parts by weight of water and molding the mixture to a shape less than 5 microns in a disc mill.
- An emulsifiable concentrate is prepared by mixing 15 parts by weight of active material, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of nonylphenol as emulsifier.
- Granules are prepared from 2 to 15 parts by weight of active material and from an inert carrier for granules like attapulgite, pumice granules and / or quartz sand.
- a suspen ⁇ sion of wettable powder of Example b is used, with a solid content of 30% which is vaporized on the surface of the granules. We dry and mix thoroughly. The proportion by weight of wettable powder is approximately 6% and that of the inert vehicle approximately 95% by weight of the finished granules.
- the fungi form spores on the entire surface of the control leaves, the extent of the disease can be assessed.
- the efficacy of the products is evaluated in relation to an untreated infested control.
- vine plants of the Riesling Ehrenfelder variety are treated with an aqueous suspension of active principle until renewal.
- the plants are inoculating them with a zoosporangia suspension of Plasmopara viticola and the wet plants are placed in a chamber at 23 ° C and a relative atmospheric humidity of 80-90%.
- the plants After 7 days of incubation, the plants are placed in a culture chamber to promote the development of fungi. The extent of the disease is then assessed.
- the degree of efficacy of the products is evaluated compared to an infested untreated control.
- Wheat of the Jubilar variety wheat is treated with an aqueous suspension of active ingredient, at the "2 leaf" stage until runoff. Once the product has vaporized dry, the plants are inoculated with an aqueous suspension of Leptosphaeris nodorum picnospores, and incubated for several hours in a room with controlled environment, at a relative atmospheric humidity of 100%. Plants are allowed to grow in a greenhouse at 90% relative atmospheric humidity until symptoms appear. The degree of effectiveness is expressed relative to an infested untreated control.
- Tomato plants of the Rheinlands Ruhn variety at stage 3, 4 leaves are treated uniformly with an aqueous suspension of active principle.
- the plants are inoculated with a suspension of zoosporangia of Phytophtora infestans and kept in a culture chamber with optimal conditions of infection for 2 days. The plants are then left to grow in a greenhouse until symptoms appear.
- Barley plants at the stage of "two leaves” are inoculated with powdery mildew conidia of barley (Erysiphe grasses p sp. Hordie) and placed in a greenhouse at 20 ° C at a relative humidity of 50%, a day after inoculation. The plants are then treated with an aqueous suspension of active ingredient. We are looking for symptoms of powdery mildew. The degree of effectiveness is evaluated in relation to the untreated infested control. At the concentration of 500 ppm the compounds A, B, C, D, E, F, G, H and I have an efficiency of 100%.
- EXAMPLE 8 EXAMPLE 8:
- the stems are inoculated with an aqueous suspension of ycellium spores of Pseudocercosporella herpotrichoids, they are left to incubate for several days in a room with a relative humidity of 100%.
- the plants are allowed to develop in a greenhouse with a relative atmospheric humidity of 95% until the appearance of symptoms.
- the degree of effectiveness is evaluated in relation to the untreated controls. At a concentration of 500 ppm the compounds A, B, C, D, E, F, G, H and I have an efficiency of 100%.
- the reaction between the compound of formula (II) and the compound of formula (III) is carried out in an aprotic dipolar solvent such as acetonitrile, in the presence of a tertiary amine tertiary like triethylamine, metallic palladium supported by charcoal, a tertiary phosphine like triphenylphosphine and a copper-based catalyst like cuprous iodide.
- an aprotic dipolar solvent such as acetonitrile
- the compounds of formula (I) can also be prepared according to a process characterized in that a compound of formula (I) in which R represents a hydrogen atom is further subjected to the action of a compound of formula ArHal , in which Ar represents an optionally substituted aryl or heteroaryl radical and Hal represents a halogen atom to obtain the corresponding compound of formula (I) in which R represents an optionally substituted aryl or heteroaryl radical.
- the compounds of formula (I), in which the radical R contains a hydroxyl function can be functionalized using an alkylating reagent such as methyl iodide or dimethyl sulfate to yield the corresponding methoxy derivatives. They can also be subject to the action of the D.A.S.T. (dimethyl amino sulfide trifluoride) to lead to the derivatives in which R contains at least one fluorine atom.
- an alkylating reagent such as methyl iodide or dimethyl sulfate
- PREPARATION 12 (E) 7- (3-fluoro 3-methyl l-butynyl) ⁇ - (methoxymethylene) l-naphthalene methyl acetate
- triphenylphosphine 3.5 g are added at 20 ° C. to a solution containing 0.6 g of the product of preparation 13, 2.24 g of carbon tetrabro ure and 6 cm 3 of methylene chloride. The reaction mixture is kept under stirring for 15 minutes. Poured into water, extracted with methylene chloride, dried and evaporated. 6.2 g of a product are obtained, which product is taken up in a mixture containing 20 cm 3 of chlorine. methylene rure and 10 cm 3 of ethyl ether. The precipitate obtained is filtered and the filtrate is concentrated.
- PREPARATION 18 (E) 7- [2- (3-chlorophenyl) ethynyl] ⁇ - (metho- xymethylene) naphthalene methyl acetate
- PREPARATION 28 (E) 7- [3- (4-chlorophenoxy) 3-methyl l-buty ⁇ nyl] ⁇ - (methoxymethylene) naphthalene methyl acetate
- PREPARATION 38 (E) 7- [2- (4-methoxy ⁇ henyl) ethynyl] ⁇ - (methoxymethylene) naphthalene methyl acetate
- PREPARATION 42 (E) 7- [3- (4-chlorophenyl) amino] 3-methyl 1- butynyl] ⁇ - (methoxymethylene) naphthalene methyl acetate
- PREPARATION 48 (E) 7- [2- (3,5-dichlorophenyl) ethynyl] ⁇ - methoxymethylene) naphthalene methyl acetate
- PREPARATION 54 (E) 7- [3- (dimethylamino) 3-methyl l-butynyl] ⁇ - (methoxymethylene) naphthalene methyl acetate
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP6522834A JPH08508987A (ja) | 1993-04-15 | 1994-04-14 | 殺菌剤組成物の製造用の7−エチニル−α−(メトキシメチレン)−1−ナフタリン酢酸誘導体 |
EP94913645A EP0693877A1 (fr) | 1993-04-15 | 1994-04-14 | UTILISATION DE DERIVES DE L'ACIDE 7-ETHYNYL $g(a)-(METHOXYMETHYLENE) 1-NAPHTALENE ACETIQUE POUR LA PREPARATION DE COMPOSITIONS FONGICIDES |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9304438A FR2703880B1 (fr) | 1993-04-15 | 1993-04-15 | Utilisation de dérivés de l'acide 7-éthynyl alpha-(méthoxy-méthylène) 1-naphtalène acétique pour la préparation de compositions fongicides. |
FR93/04438 | 1993-04-15 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1994023576A1 true WO1994023576A1 (fr) | 1994-10-27 |
Family
ID=9446098
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR1994/000417 WO1994023576A1 (fr) | 1993-04-15 | 1994-04-14 | UTILISATION DE DERIVES DE L'ACIDE 7-ETHYNYL α-(METHOXYMETHYLENE) 1-NAPHTALENE ACETIQUE POUR LA PREPARATION DE COMPOSITIONS FONGICIDES |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP0693877A1 (fr) |
JP (1) | JPH08508987A (fr) |
CA (1) | CA2160577A1 (fr) |
FR (1) | FR2703880B1 (fr) |
WO (1) | WO1994023576A1 (fr) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2727408A1 (fr) * | 1994-11-29 | 1996-05-31 | Roussel Uclaf | Nouvelles oximes derivees de l'acide 7-ethynyl alpha-(oxo) 1-naphtalene acetique, leur procede de preparation et leur utilisation comme pesticides |
WO1996029305A1 (fr) * | 1995-03-21 | 1996-09-26 | Agrevo Uk Limited | Composes fongicides |
WO1996029301A1 (fr) * | 1995-03-21 | 1996-09-26 | Agrevo Uk Limited | Composes fongicides |
WO1997007099A1 (fr) * | 1995-08-16 | 1997-02-27 | Agrevo Uk Limited | Derives de l'acide alpha-methoxyimino-naphtylacetique ou alpha m ethoxymethylene et leur utilisation comme fongicides |
WO2019210245A1 (fr) * | 2018-04-26 | 2019-10-31 | 1,4Group, Inc. | Procédé de lutte contre le fusarium sur la pomme de terre à l'aide de naphtalène à alkyle inférieur |
WO2022004702A1 (fr) * | 2020-06-30 | 2022-01-06 | 住友化学株式会社 | PROCÉDÉ DE LUTTE CONTRE LE CHAMPIGNON DE LA ROUILLE DU SOJA PRÉSENTANT UNE RÉSISTANCE AUX FONGICIDES QoI |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0267734A2 (fr) * | 1986-11-11 | 1988-05-18 | Zeneca Limited | Composés chimiques |
EP0566455A1 (fr) * | 1992-04-14 | 1993-10-20 | Roussel Uclaf | Nouveaux dérivés de l'acide 7-éthynyl alpha-(méthoxyméthylène) 1-naphtalène acétique, leur procédé de préparation et leur application comme pesticides |
-
1993
- 1993-04-15 FR FR9304438A patent/FR2703880B1/fr not_active Expired - Fee Related
-
1994
- 1994-04-14 WO PCT/FR1994/000417 patent/WO1994023576A1/fr not_active Application Discontinuation
- 1994-04-14 EP EP94913645A patent/EP0693877A1/fr not_active Withdrawn
- 1994-04-14 CA CA 2160577 patent/CA2160577A1/fr not_active Abandoned
- 1994-04-14 JP JP6522834A patent/JPH08508987A/ja active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0267734A2 (fr) * | 1986-11-11 | 1988-05-18 | Zeneca Limited | Composés chimiques |
EP0566455A1 (fr) * | 1992-04-14 | 1993-10-20 | Roussel Uclaf | Nouveaux dérivés de l'acide 7-éthynyl alpha-(méthoxyméthylène) 1-naphtalène acétique, leur procédé de préparation et leur application comme pesticides |
Non-Patent Citations (1)
Title |
---|
K. BEAUTEMENT ET AL.: "fungicidal beta-methoxyacrylates", PESTICIDE SCIENCE, vol. 31, no. 4, 1991, BARKING GB, pages 499 - 519 * |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2727408A1 (fr) * | 1994-11-29 | 1996-05-31 | Roussel Uclaf | Nouvelles oximes derivees de l'acide 7-ethynyl alpha-(oxo) 1-naphtalene acetique, leur procede de preparation et leur utilisation comme pesticides |
WO1996016933A1 (fr) * | 1994-11-29 | 1996-06-06 | Hoechst Schering Agrevo S.A. | Nouvelles oximes derivees de l'acide 7-ethynyl alpha-(oxo) 1-naphtalene acetique, leur procede de preparation et leur utilisation comme pesticides |
WO1996029305A1 (fr) * | 1995-03-21 | 1996-09-26 | Agrevo Uk Limited | Composes fongicides |
WO1996029301A1 (fr) * | 1995-03-21 | 1996-09-26 | Agrevo Uk Limited | Composes fongicides |
WO1997007099A1 (fr) * | 1995-08-16 | 1997-02-27 | Agrevo Uk Limited | Derives de l'acide alpha-methoxyimino-naphtylacetique ou alpha m ethoxymethylene et leur utilisation comme fongicides |
WO2019210245A1 (fr) * | 2018-04-26 | 2019-10-31 | 1,4Group, Inc. | Procédé de lutte contre le fusarium sur la pomme de terre à l'aide de naphtalène à alkyle inférieur |
CN112469276A (zh) * | 2018-04-26 | 2021-03-09 | 1,4集团公司 | 使用低级烷基萘防治马铃薯上的镰孢菌的方法 |
WO2022004702A1 (fr) * | 2020-06-30 | 2022-01-06 | 住友化学株式会社 | PROCÉDÉ DE LUTTE CONTRE LE CHAMPIGNON DE LA ROUILLE DU SOJA PRÉSENTANT UNE RÉSISTANCE AUX FONGICIDES QoI |
Also Published As
Publication number | Publication date |
---|---|
EP0693877A1 (fr) | 1996-01-31 |
FR2703880B1 (fr) | 1995-06-02 |
JPH08508987A (ja) | 1996-09-24 |
CA2160577A1 (fr) | 1994-10-27 |
FR2703880A1 (fr) | 1994-10-21 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US5250530A (en) | Aminopyrimidine derivatives, and their use as fungicides | |
US5668140A (en) | Substituted 4-aminopyrimidines, processes for their preparation, and their use as pesticides | |
JP2010538029A (ja) | 新規殺菌剤 | |
KR20010089820A (ko) | 신규한 프로파길에테르 유도체 | |
JPS6147403A (ja) | N‐アセトニルベンヅアミドを含有する殺菌性組成物を用いる植物生病原生物である菌類の防除方法 | |
EP0703899A1 (fr) | Arylacetamides, leur procede de preparation, compositions les contenant et leur utilisation en tant que fongicides | |
JP3046354B2 (ja) | 置換されたピリジン、それらの製造方法、及びそれらを農薬及び殺菌剤として使用する方法 | |
AU703538B2 (en) | Heterocyclylamino- and heterocyclyloxy-cycloalkyl derivatives, their preparation and their use as pesticides and fungicides | |
CS269997B2 (en) | Fungicide and method of active substances production | |
OA10106A (fr) | (Hetero)-aryl-alkyl-cetoxim-o-ethers substitues acaricides insecticides et nematocides procede pour leur preparation agents les contenant et leur utilisation en tant qu'agents de lutte antiparaasitaire | |
JP2806441B2 (ja) | チオールカルボン酸エステル及びこれを含有する殺菌剤 | |
WO1994023576A1 (fr) | UTILISATION DE DERIVES DE L'ACIDE 7-ETHYNYL α-(METHOXYMETHYLENE) 1-NAPHTALENE ACETIQUE POUR LA PREPARATION DE COMPOSITIONS FONGICIDES | |
CN1091444C (zh) | 用作杀菌剂的杂环取代的异噁唑啉类化合物 | |
US5424480A (en) | Substituted N-hydroxycinnamamides, processes for their preparation, compositions containing them, and their use | |
US5877322A (en) | Substituted pyridines, their preparation, and their use as pesticides and fungicides | |
JPH05501550A (ja) | ピリミジン誘導体、それらの製造方法、それらを含有する薬剤及びそれらを殺菌剤として使用する方法 | |
WO1996011913A1 (fr) | Heterocycles cycloalkylamines et cycloalcoxy, leur procede de preparation et leur utilisation comme pesticides | |
JP4545942B2 (ja) | 新規アルファースルフェンイミノ酸誘導体 | |
JP3181670B2 (ja) | フェニルイミダゾール化合物、その製造方法及びそれらを含有する農園芸用殺菌剤 | |
EA011548B1 (ru) | НОВЫЕ ПРОИЗВОДНЫЕ ФЕНЕТИЛАМИДОВ α-КАРБОНОВЫХ ИЛИ α-ТИОКАРБОНОВЫХ КИСЛОТ | |
EP1021399A2 (fr) | Fongicides a groupes hydroximiques et hydrazoniques | |
JP2909469B2 (ja) | 病害に対する植物の防護剤 | |
KR100508496B1 (ko) | 불소화 스티렌 치환기를 가진 프로페노익 에스테르 및아미드 유도체, 이의 제조방법 및 이를 포함하는 살균제조성물 | |
KR0146504B1 (ko) | 아졸아미드 유도체 | |
WO1999051579A1 (fr) | Composes fongicides comportant un groupe hydroximique ou hydrazonique |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): CA JP US |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE |
|
DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
ENP | Entry into the national phase |
Ref document number: 1995 537719 Country of ref document: US Date of ref document: 19951012 Kind code of ref document: A |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2160577 Country of ref document: CA |
|
WWE | Wipo information: entry into national phase |
Ref document number: 1994913645 Country of ref document: EP |
|
WWP | Wipo information: published in national office |
Ref document number: 1994913645 Country of ref document: EP |
|
WWW | Wipo information: withdrawn in national office |
Ref document number: 1994913645 Country of ref document: EP |