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WO1998003464A1 - Pesticides - Google Patents

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Publication number
WO1998003464A1
WO1998003464A1 PCT/EP1997/003968 EP9703968W WO9803464A1 WO 1998003464 A1 WO1998003464 A1 WO 1998003464A1 EP 9703968 W EP9703968 W EP 9703968W WO 9803464 A1 WO9803464 A1 WO 9803464A1
Authority
WO
WIPO (PCT)
Prior art keywords
atoms
optionally substituted
alkyl
halogen
carbon
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP1997/003968
Other languages
English (en)
Inventor
Jean-Louis Brayer
Nicole Reinier
Bernard Roisil
Sylvain Laugraud
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Laugraud Bruno
Laugraud Philippe
Laugraud Pierre
Laugraud Rolande
Sollossi Martine
Hoechst Schering Agrevo SA
Original Assignee
Laugraud Bruno
Laugraud Philippe
Laugraud Pierre
Laugraud Rolande
Sollossi Martine
Hoechst Schering Agrevo SA
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 Laugraud Bruno, Laugraud Philippe, Laugraud Pierre, Laugraud Rolande, Sollossi Martine, Hoechst Schering Agrevo SA filed Critical Laugraud Bruno
Priority to AU39406/97A priority Critical patent/AU3940697A/en
Publication of WO1998003464A1 publication Critical patent/WO1998003464A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/734—Ethers
    • C07C69/736—Ethers the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring
    • 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
    • A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
    • A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof

Definitions

  • the present invention relates to new derivatives of ⁇ -methoxyacrylic acid, process for their preparation and their application as pesticides
  • V is an oxygen or a sulfur atom
  • X and Y which may be the same or different, are hydrogen or halogen atoms, or optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkynyl, haloalkyl, alkoxy, haloalkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted acyloxy, optionally substituted ammo, acylamino, nitro, nitrile, -CO2 3 , -C0 ⁇ MR 4 R5, or COR ⁇ groups; or the groups X and Y, when they are in adjacent positions on the phenyl ring, may join to form a fused ring, either aromatic or aliphatic, optionally containing one or more heteroatoms; and Z is optionally substituted methylene optionally substituted ammo, oxygen or sulfur and when Z is
  • , R2 and R3 which may be the same as or different from each other are a) alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy or alkanoyioxy, each of which is straight, branched or cyclic, comprising up 8 carbon atoms, optionally substituted by one or more halogen atoms and optionally interrupted by one or more oxygen atoms, b) phenyl or phenoxy, optionally substituted by one or more halogen atoms, one or more hydroxy radicals, one or more alkyl radicals which are linear or branched and are optionally substituted by one or more halogen atoms, one or more alkoxy or alkylthio radicals, which are optionally substituted by one or more halogen atoms, one or more hydroxy radicals, (which may be este ⁇ fied), or one or more cyano radicals, c) R -] and R2 can be
  • X and R4 together with atoms to which they are attached, can form a ring optionally containing one or more hetero atoms selected from oxygen, nitrogen and sulfur.
  • the geometry of the double bond of the ⁇ -methoxyacrylate part of the molecule can be Z, E or a mixture of E and Z, but is preferably Z.
  • - alkyl is preferably methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert- butyl,
  • - cycloalkyl is preferably cyciopropyl, cyclobutyl or cyclopentyl
  • -alkenyl is preferably vinyl, propenyl or butenyl
  • -alkynyl is preferably acetylenyl, propynyl or butynyl.
  • Preferred compounds are those where: two of R -
  • X is hydrogen
  • the compounds of formula (I) have interesting properties which allow their use in the control of parasites. They can be active against plant pests which act through the soil or above the soil parts of the plant, are active against parasites of buildings and also against parasites of warm-blooded animals.
  • the compounds of formula (I) have insecticidal and acaricidal properties as well as fungicidal properties.
  • the products of formula (I) can also be used for combating insects in buildings and for combating particularly flies, mosquitoes and cockroaches.
  • the products of formula (I) can also be used for combating insects and other soil parasites for example Coleoptera, such as Diabrotica, wire worms and cockchafer larvae, my ⁇ apods such as centipedes and millipedes, Diptera such as gall-gnats and Lepidoptera such as cut-worms.
  • the compounds of formula (I) can be used for combating parasitic aca ⁇ ds of animals for combating for Example ticks and especially ticks of the genus
  • Boophilos those of the genus Hyalomma, those of the genus Amblyomma and those of the genus Ripicephalus and for combating all sorts of mites and especially sarcoptic, psoroptic and cho ⁇ optic mites
  • the active ⁇ ngred ⁇ ent(s) can optionally include one or more other pesticides.
  • These compositions can be in the form of powders, granules, suspensions, emulsions, solutions, solutions for aerosols, combustible coils, baits or other preparations conventionally used in this class of compounds.
  • the compositions contain in general a carrier and/or a non-ionic surface active agent to ensure a uniform dispersion of the constituent substances of the mixture
  • the carrier used can be a liquid, such as water, alcohol, hydrocarbons or other organic solvents, a mineral, animal or vegetable oil, a powder such as talc, clay, a silicate, kieselguhr or a combustible solid.
  • the insecticide compositions according to the invention preferably contain from 0.005% to 10% by weight of active material
  • compositions according to the invention are used in the form of fumigant composition.
  • compositions according to the invention can thus be advantageously formed for the non-active part of a combustible insecticidal serpent (or coil) or further from an incombustible fibrous substrate.
  • the fumigant is obtained after incorporation of the active material is placed on a heating apparatus such as an electrical emanator.
  • the inner support can be for example a compound of pyrethrum residue, tabu powder (or powder of the leaves of Machilus thumbergii), pyrethrum stalk powder, cedar leaf powder, wood powder, such as pine sawdust), starch and coconut husk powder.
  • the dose of the active ingredient can be for example from 0.03 to 1 % by weight.
  • the dose of active material can then be for example from 0.03 to 95% by weight.
  • compositions according to the invention for use in buildings can also be obtained by preparing a pulve ⁇ sable oil based on the active principle, this oil containing the wick of a lamp and thus being capable of combustion.
  • the concentration of the active ingredient incorporating the oil is preferably from 0.03 to 95% by weight.
  • the acaricidal and nematicidal compositions can be present, notably in the form of a powder, granule, suspension, emulsion or solution.
  • wettabie powders are preferably used for foliar application containing from 1 to 80% of active material where the liquid for spraying the leaves contains from 1 to 500 grams per litre of the active ingredient.
  • Foliar dusting powders can also be used containing from 0.05 to 3% of active agent.
  • liquids for treating soils containing from 30 to 500 grams per litre of active ingredient are preferably used.
  • the compounds of the invention have activity against pathogens of Deuteromycete, Ascomycete, Phycomycete and Basidiomycete origin, especially against fungal diseases of plants, e.g. mildews and particularly cereal powdery mildew (Erysiphe gramims), cucumber powdery mildew [Erysiphe cichoracaerum), vine downy mildew [P/asmopara viticola) and vine powdery mildew ⁇ Uncin ⁇ /a necator), rice blast (Pyricula ⁇ a oryzae), cereal eyespot (Pseudocercosporella herpotrichoides) , rice sheath blight (Pellicularia sasakii), grey mould (Botrytis cinerea), wheat brown rust (Puccinia recondita), late tomato or potato blight (Phytophthora infestans), apple scab [Ventur/a inaequalis) and glume blot
  • the compounds of the invention can also be used in various industrial sectors, for example for protecting wood and as a paint preservative.
  • the invention also extends to fungicidal compositions which comprise besides the compounds of formula I appropriate formulation agents.
  • compositions of the invention in general comprise from 1 to 95% by weight of the active ingredient.
  • the possible formulations vary as a function of the biological and physicochemical parameters. They can be for example wettabie powders, emulsifiable concentrates, aqueous solutions, emulsions, vapo ⁇ sable solutions, dispersions in oil in or in water, suspo-emulsions, powders, seed treatment agents, granules for example microgranules, pulve ⁇ sable granules, coated granules, absorption granules, water-dispersible granules, ULV formulations, micro-capsules, waxes or baits.
  • compositions according to the invention can in addition optionally contain one or more other pesticidal agents.
  • the invention also includes a process characterised in that a compound of formula (ID
  • R - j , R2 and R3 have the same meanings as above.
  • the compound of formula I in which R3 is hydroxy can be prepared in a similar manner to above using a compound of formula (II) in which R3 is hydroxy.
  • 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 or DMF, in the presence of a tertiary amine, such as triethylamine, and in the presence of palladium, for example present as PdCl2(PPh3)2- or palladium metal supported on carbon, a tertiary phosphine, such as triphenylphosphi ⁇ e and a catalyst based on copper such as copper iodide.
  • Hal preferably represents an atom of bromine or iodine.
  • the compounds of formula (II) can be prepared as follows
  • the starting product can be prepared according to the following processes.
  • Example 1 A mixture, comprising methyl 2-[5-bromo-2-chlorophenoxy]-3-methoxy- 2-propenoate ( 1 .25 g), acetonitrile ( 1 2.5 ml), 3-butoxy-3-methyl-1 -pentyne ( 1 .1 5 g), PdCl2( ⁇ 3>2 (80 mg), copper iodide (30 mg), triphenyl phosphine ( 1 20 mg) and t ⁇ ethylamine (3 ml), was heated under reflux for 5 hours, The mixture was added to N hydrochloric acid (50 ml) and ice, extracted with diethyl ether, dried and evaporated to dryness.
  • N hydrochloric acid 50 ml
  • ice extracted with diethyl ether
  • a suspension of 9 g of the product obtained in stage B in b ⁇ s(d ⁇ methyiam ⁇ o)te/ - butoxymethane (75 ml) was heated for 1 hour at 80°C. The temperature was allowed to return to 20 °C, the mixture poured into water and extracted with methylene chloride. The combined organic phases were dried over magnesium sulfate and evaporated under reduced pressure.
  • Test Example a Fungicide tests Compounds are assessed for activity against one or more of the following:
  • Pyricularia oryzae rice blast Pelliculana sasakn- rice sheath blight .
  • Botrytis cmerea grey mould
  • Aqueous solutions or dispersions of the compounds at the desired concentration, including a wetting agent, were applied by spray or by drenching the stem base of the test plants, as appropriate. Plants or plant parts were then inoculated with appropriate test pathogens and kept under controlled environment conditions suitable for maintaining plant growth and development of the disease. After an appropriate time, the degree of infection of the affected part of the plant was visually estimated. Compounds are assessed on a score of 1 to 3 where 1 is little or no control, 2 is moderate control and 3 is good to total control. At a concentration of 500 ppm (w/v) or less, the following compounds scored 2 or more against the fungi specified Phytophthora infesta ⁇ s 104-9 and 111-3
  • Plasmopara viticoia 4 5, 7, 12, 13, 65, 69, 70, 71, 74, 76, 77, 81-3, 85, 103-9 and 111-113
  • Bean plants comprising two leaves infested with 30 female ⁇ rticae per leaf were put under an aerated hood under an illuminated ceiling under constant light conditions. The plants were treated using a Fisher gun with an aqueous acetone solution of test compound at various concentrations.4 ml of test solution were applied to each plant. The plants were allowed to dry over half an hour and then the infestation was allowed to proceed. The degree of control of the Tetranychus was determined at the end of 3 days. Results: At a dose of 100 ppm or less, the following compounds gave at least 50% control of the aca ⁇ ds:

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

Abstract

Composés de formule (I), dans laquelle R1, R2 et R3 sont (a) alkyle, alcoxy, alcényle, alcényloxy, alcynyle, alcynyloxy ou alcanoyloxy linéaire, ramifié ou cyclique, comprenant jusqu'à 8 atomes de carbone, éventuellement substitué par un ou plusieurs atomes d'halogène et éventuellement interrompu par un ou plusieurs atomes d'oxygène; (b) phényle ou phénoxy éventuellement substitué par un ou plusieurs atomes d'halogène, un ou plusieurs radicaux hydroxy, un ou plusieurs radicaux alkyle linéaires ou ramifiés et éventuellement substitués par un ou plusieurs atomes d'halogène, un ou plusieurs radicaux alcoxy ou alkylthio éventuellement substitués par un ou plusieurs atomes d'halogène, un ou plusieurs radicaux hydroxy (éventuellement estérifiés) ou un ou plusieurs radicaux cyano; (c) tels que R1 et R2 peuvent former, avec l'atome de carbone auquel ils sont rattachés, une double liaison carbone; (d) tels que R1 et R2 peuvent former, avec le carbone auquel ils sont rattachés, un cycle comprenant jusqu'à 8 atomes de carbone et qui peut comprendre un ou plusieurs hétéroatomes choisis parmi oxygène, soufre et azote; R4 est halogène ou un radical alkyle, alcényle, alcynyle, alcoxy, alcényloxy, alcynyloxy, alkylthio, alcénylthio ou alcynylthio, dont chacun est éventuellement substitué par un ou plusieurs atomes d'halogène et comprend jusqu'à 11 atomes de carbone, un radical phényle éventuellement substitué tel que défini sous (b), CN, NO2, NH2, N(alk1)alk2, CO2alk3, où alk1, alk2 et alk3, qui peuvent être identiques ou différents, représentent alkyle comprenant jusqu'à 8 atomes de carbone; X a la même signification que R4 ou peut être hydrogène; ou X et R4 forment, avec les atomes auxquels ils sont rattachés, un noyau contenant éventuellement un ou plusieurs hétéroatomes choisis entre oxygène, azote et soufre. Ces composés présentent une activité pesticide, en particulier fongicide ou acaricide.
PCT/EP1997/003968 1996-07-24 1997-07-22 Pesticides Ceased WO1998003464A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU39406/97A AU3940697A (en) 1996-07-24 1997-07-22 Pesticides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR9609286A FR2751642B1 (fr) 1996-07-24 1996-07-24 Nouveaux derives de l'acide beta-methoxy acrylique, leur procede de preparation et leur application comme pesticides
FR96/09286 1996-07-24

Publications (1)

Publication Number Publication Date
WO1998003464A1 true WO1998003464A1 (fr) 1998-01-29

Family

ID=9494404

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1997/003968 Ceased WO1998003464A1 (fr) 1996-07-24 1997-07-22 Pesticides

Country Status (4)

Country Link
AU (1) AU3940697A (fr)
FR (1) FR2751642B1 (fr)
WO (1) WO1998003464A1 (fr)
ZA (1) ZA976536B (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998034898A1 (fr) * 1997-02-06 1998-08-13 Rhone-Poulenc Agro Derives d'acide phenoxyacetique et leur utilisation en tant qu'herbicides
WO2000003975A3 (fr) * 1998-07-16 2000-08-03 Rhone Poulenc Agriculture Derives d'arylvinylether et leur utilisation comme herbicides
WO2020027214A1 (fr) 2018-07-31 2020-02-06 住友化学株式会社 PROCÉDÉ DE LUTTE CONTRE LA ROUILLE DU SOJA RÉSISTANT AUX INHIBITEURS DE Qo
WO2020193387A1 (fr) 2019-03-22 2020-10-01 Syngenta Crop Protection Ag Composés fongicides
WO2020262648A1 (fr) 2019-06-28 2020-12-30 住友化学株式会社 Dérivé d'ester (méth)acrylique, et application et intermédiaire de production de celui-ci
WO2021153760A1 (fr) * 2020-01-31 2021-08-05 住友化学株式会社 Composition de lutte contre les maladies des plantes, et procédé de lutte contre les maladies des plantes
WO2021153759A1 (fr) * 2020-01-31 2021-08-05 住友化学株式会社 Composition de lutte contre les maladies des plantes, et procédé de lutte contre les maladies des plantes
WO2021153758A1 (fr) * 2020-01-31 2021-08-05 住友化学株式会社 Composition de lutte contre les maladies des plantes, et procédé de lutte contre les maladies des plantes
WO2021176057A1 (fr) 2020-03-05 2021-09-10 Syngenta Crop Protection Ag Compositions fongicides
CN114988981A (zh) * 2022-04-26 2022-09-02 盐城工学院 一种α-三氟甲基芳丙炔类化合物的制备方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0212859A2 (fr) * 1985-08-22 1987-03-04 Imperial Chemical Industries Plc Fongicides
EP0718292A1 (fr) * 1992-08-11 1996-06-26 Basf Aktiengesellschaft Dérivés acétyléniques et leur application comme agents phytosanitaires

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0212859A2 (fr) * 1985-08-22 1987-03-04 Imperial Chemical Industries Plc Fongicides
EP0718292A1 (fr) * 1992-08-11 1996-06-26 Basf Aktiengesellschaft Dérivés acétyléniques et leur application comme agents phytosanitaires

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6337306B1 (en) 1997-02-06 2002-01-08 Rhone-Poulenc Agro Phenoxyacetic acid derivatives and their use as herbicides
WO1998034898A1 (fr) * 1997-02-06 1998-08-13 Rhone-Poulenc Agro Derives d'acide phenoxyacetique et leur utilisation en tant qu'herbicides
WO2000003975A3 (fr) * 1998-07-16 2000-08-03 Rhone Poulenc Agriculture Derives d'arylvinylether et leur utilisation comme herbicides
US20210307328A1 (en) * 2018-07-31 2021-10-07 Sumitomo Chemical Company, Limited METHOD FOR CONTROLLING SOYBEAN RUST FUNGUS HAVING RESISTANCE AGAINST Qo SITE INHIBITOR
WO2020027214A1 (fr) 2018-07-31 2020-02-06 住友化学株式会社 PROCÉDÉ DE LUTTE CONTRE LA ROUILLE DU SOJA RÉSISTANT AUX INHIBITEURS DE Qo
US11849728B2 (en) 2018-07-31 2023-12-26 Sumitomo Chemical Company, Limited Method for controlling soybean rust fungus having resistance against Qo site inhibitor
WO2020193387A1 (fr) 2019-03-22 2020-10-01 Syngenta Crop Protection Ag Composés fongicides
US12262710B2 (en) 2019-03-22 2025-04-01 Syngenta Crop Protection Ag Fungicidal compounds
WO2020262648A1 (fr) 2019-06-28 2020-12-30 住友化学株式会社 Dérivé d'ester (méth)acrylique, et application et intermédiaire de production de celui-ci
WO2021153760A1 (fr) * 2020-01-31 2021-08-05 住友化学株式会社 Composition de lutte contre les maladies des plantes, et procédé de lutte contre les maladies des plantes
WO2021153758A1 (fr) * 2020-01-31 2021-08-05 住友化学株式会社 Composition de lutte contre les maladies des plantes, et procédé de lutte contre les maladies des plantes
WO2021153759A1 (fr) * 2020-01-31 2021-08-05 住友化学株式会社 Composition de lutte contre les maladies des plantes, et procédé de lutte contre les maladies des plantes
WO2021176057A1 (fr) 2020-03-05 2021-09-10 Syngenta Crop Protection Ag Compositions fongicides
CN114988981A (zh) * 2022-04-26 2022-09-02 盐城工学院 一种α-三氟甲基芳丙炔类化合物的制备方法
CN114988981B (zh) * 2022-04-26 2023-12-22 盐城工学院 一种α-三氟甲基芳丙炔类化合物的制备方法

Also Published As

Publication number Publication date
FR2751642A1 (fr) 1998-01-30
ZA976536B (en) 1998-11-30
AU3940697A (en) 1998-02-10
FR2751642B1 (fr) 1998-09-11

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