EP0000962B1 - Composition pesticide et procédé pour détruire les organismes nuisibles - Google Patents

Composition pesticide et procédé pour détruire les organismes nuisibles Download PDF

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Publication number
EP0000962B1
EP0000962B1 EP78200099A EP78200099A EP0000962B1 EP 0000962 B1 EP0000962 B1 EP 0000962B1 EP 78200099 A EP78200099 A EP 78200099A EP 78200099 A EP78200099 A EP 78200099A EP 0000962 B1 EP0000962 B1 EP 0000962B1
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Prior art keywords
group
carbon atoms
alkyl
composition according
composition
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EP78200099A
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German (de)
English (en)
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EP0000962A1 (fr
Inventor
John Stewart Badmin
Robert John Knight
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Shell Internationale Research Maatschappij BV
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Shell Internationale Research Maatschappij BV
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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
    • 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
    • A01N37/52—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 groups, e.g. carboxylic acid amidines
    • 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof

Definitions

  • This invention relates to a pesticidal composition and to a method of combating pests.
  • compositions including the known acaricide, N,N-di(2,4-xylyliminomethyl)-methylamine and certain insecticides possess synergistic activity with respect to acarid pests; that is to say, the activity of the combination of the two pesticides produces a more-than- additive pesticidal effect.
  • the present invention provides a pesticidal composition which comprises N,N-di-(2,4-xylyliminomethyl)methylamine (hereinafter referred to as "amitraz”) characterized in that the composition includes insecticide having the general formula: wherein A is an optionally-substituted aralkyl, alkyl or cycloalkyl group, R is hydrogen, cyano or ethynyl, X is alkyl, alkenyl, aralkyl or aryloxy, and n is 1 to 5.
  • an alkyl, cycloalkyl or alkenyl group represented by A or X preferably contains up to 6 carbon atoms and an aralkyl or aryloxy group represented by A or X preferably contains up to 10 carbon atoms.
  • insecticide I can exist in the form of optical isomers or cis-trans- isomers and in the composition according to the invention as individual isomer or mixture of isomers including racemates may be employed.
  • A represents an optimally-substituted aralkyl group in general formula 1.
  • Especially preferred compounds of the general formula I are those in which A represents a substituted benzyl group of the general formula: wherein Z represents a halogen, preferably a chlorine, atom, or an alkoxy group having 1 to 4 carbon atoms, for example a methoxy group, and Q represents an alkyl group having from 1 to 6 carbon atoms, especially a branched-chain group, for example an isopropyl group.
  • the most preferred compounds of the general formula I are those wherein A represents an alpha-isopropyl-4-chlorobenzyl group, R represents a hydrogen atom or a cyano group, n is 1, and X represents a 3-phenoxy group, for example alpha-cyano-3-phenoxybenzyl 2-(4-chlorophenyl)-3-methylbutanoate.
  • A represents an optionally-substituted cycloalkyl group in general formula I
  • the preferred compounds of this type are those wherein A represents a cyclopropyl group of formula: wherein R a and R b each individually represent an alkyl group having from 1 to 6 carbon atoms, especially methyl or a halogen, especially chlorine, bromine or fluorine atom; or R a and R b together represent an alkylene group having from 2 to 6, especially 3, carbon atoms; or R a represents a hydrogen atom and R b represents an alkenyl group having from 2 to 6 carbon atoms, especially an isobutenyl group, or a haloalkenyl group having from 2 to 6 carbon atoms and from 1 to 3 chlorine or bromine atoms, especially a mono- or dichlorovinyl group; R c and R d both represent an alkyl group having 1 to 6.
  • R c and R d together represent an alkylene group having from 2 to 6, especially 3, carbon atoms.
  • A may represent a 2,2,3,3-tetramethylcyclopropyl group while R represents a hydrogen atom or a cyano group, n -is 1 and X is 3-phenoxy.
  • the mixture of amitraz and the insecticide (I) not only produces a pesticide having a markedly wider spectrum of activity than the insecticide (I) or the amitraz alone, but also produces a surprising synergistic effect with respect to acarids. e.g., glasshouse red spider mite. Tetranychus urticae.
  • the mixture also possesses useful properties with respect to the eggs of lepidopterous and acharine pests; it has uses in the agrochemical and animal health fields.
  • the weight ratio of the insecticide (I) to amitraz may be in the range 5:1 to 1:50.
  • the pesticidal composition according to the invention preferably also comprises a carrier, especially at least two carriers, at least one of which is a surface-active agent.
  • a carrier may be a solid or liquid material, which may be inorganic or organic and of synthetic or natural origin.
  • Typical solid carriers include natural and synthetic clays and silicates, for example, natural silicas, for example diatomaceous earths, and aluminium silicates, for example kaolinites, montmorillonites and micas.
  • Typical liquid carriers are ketones, for example methylcyclohexanone, aromatic hydrocarbons, for example methylnaphthalenes, petroleum fractions, for example petroleum xylenes and light mineral oils, and chlorinated hydrocarbons, for example carbon tetrachloride. Mixtures of liquids are often suitable.
  • a surface-active agent may be an emulsifying agent or a dispersing agent or a wetting agent; it may be non-ionic or ionic. Any of the surface-active agents usually applied in formulating insecticides may be used.
  • Suitable surface-active agents are the sodium and calcium salts of polyacrylic acids and lignin sulphonic acids; the condensation products of fatty acids of aliphatic amines or amides containing at least 12 carbon atoms in the molecule with ethylene oxide and/or propylene oxide; fatty acid esters of glycerol, sorbitan, sucrose or pentaerythritol, condensates of these with ethylene oxide and/or propylene oxide; condensation products of fatty alcohols or alkyl phenols, for example p-octylphenol or p-octylcresol, with ethylene oxide and/or propylene oxide; sulphates or sulphonates of these condensation products; alkali or alkaline earth metal salts, preferably sodium salts, of sulphuric or sulphonic acid esters containing at least 10 carbon atoms in the molecule, for example sodium lauryl sulphate, sodium secondary alkyl sulphates, sodium
  • composition of the invention may for example be formulated as a wettable powder, microcapsules, a dust, granules, a solution, an emulsifiable concentrate, an emulsion, a suspension concentrate or an aerosol.
  • the composition may have controlled release properties, or may be suitable for use as a bait.
  • Wettable powders usually contain 25, 50 or 75%w of active ingredient and may contain, in addition to inert solid material, 3-10% w of a dispersing agent and, where necessary, 0-1 O%w of a stabilizer, a penetrant and/or a sticker.
  • a dust is usually formulated as a dust concentrate having a composition similar to that of a wettable powder but without a dispersant, and is diluted in the field with further solid carrier to give a composition usually containing 10%w of active ingredient.
  • Granules usually have a size in the range of from 10 to 100 BS mesh (1.676-0.152 mm) and may be manufactured by agglomeration or impregnation techniques. Generally, granules will contain 25%w active ingredient and 0-1 O%w of additives, for example a stabilizer, slow-release modifier and/or a binding agent.
  • Emulsifiable concentrates usually contain, in addition to a solvent, and, when necessary, cosolvent, 10-50%w/v active ingredient, 2-20%w/v emulsifier and 0-20%w/v of other additives, for example a stabilizer, a penetrant and/or a corrosion inhibitor.
  • a suspension concentrate is a stable, non- sedimenting, flowable product and usually contains 10-75%w active ingredient, 0.5-15%w of dispersing agent, 0.
  • suspending agent for example protective colloid and for a thixotropic agent
  • other additives including, for example, a defoamer, a corrosion inhibitor, a stabilizer, a penetrant and/or a sticker, and as dispersant, water or an organic liquid in which the active ingredient is substantially insoluble; certain organic additives and/or inorganic salts may be dissolved in the dispersant to assist in preventing sedimentation or as anti-freeze for water.
  • aqueous dispersions and emulsions formed by diluting a wettable powder or an emulsifiable concentrate of the invention with water also lie within the scope of the present invention.
  • Such dispersions and emulsions may be of the water-in-oil or of the oil-in-water type, and may have a thick "mayonnaise"-like consistency.
  • a composition of the invention may also contain other ingredients, for example, one or more other compounds possessing pesticidal, herbicidal or fungicidal properties, or attractants, for example pheromones or food ingredients, for use in baits and trap formulations.
  • other ingredients for example, one or more other compounds possessing pesticidal, herbicidal or fungicidal properties, or attractants, for example pheromones or food ingredients, for use in baits and trap formulations.
  • the invention also includes a method of combating pests at a locus characterized in that a pesticidal composition according to the invention is applied to the locus.
  • the invention is further illustrated by the following Example, in which the joint action of two pesticides was analyzed according to the method of Yun-Pei Sun and E. R. Johnson, Journal of Economic Entomology, 1960, Volume 53, No. 5, pp. 887-892.
  • the joint action of two pesticides was analyzed by determining the actual toxicity indices of the components and of mixtures of the compounds by reference to dosage-mortality curves.
  • the theoretical toxicity of the mixture is equal to the sum over both components of the percentage of each individual compound multiplied by its respective toxicity index. Therefore, the joint toxicity or co-toxicity
  • a coefficient of a mixture near 100 indicates probability of similar action by the two pesticides; independent action usually should give a coefficient less than 100, while a coefficient significantly above 100 strongly indicates synergism.
  • amitraz, compound Y and their mixtures were assessed by the following method.
  • the compounds and mixtures were formulated as solutions or suspensions in water containing 20% by weight of acetone and 0.05% by weight of Triton X-100 (Trade Mark) as wetting agent.
  • the formulations contained 0.4% by weight of the compound or mixture to be tested and were diluted to produce formulations containing various concentrations.
  • Leaf discs cut from French bean plants were sprayed with the formulations and left for -1 to 1 hour drying period. Each leaf disc was then inoculated with 10 red spider mites and mortality counts made 24 hours after inoculation. From these results the LC 50 's (the concentration by weight of active material in the spray required to kill 50% of the mite population) could be calculated.

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  • 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)

Claims (8)

1. Composition pesticide qui comprend de la N,N-di(2,4-xylyl iminométhyl)-méthylamine, caractérisée en ce que la composition comprend un insecticide ayant la formule générale:
Figure imgb0017
dans laquelle A est un groupe aralkyl, alkyl ou cycloalkyle éventuellement substitué, R est un atome d'hydrogène ou un radical cyano ou éthynyl; X est un groupe alkyl, alcényl, aralkyl ou aryloxy et n est un entier de 1 à 5.
2. Composition selon la revendication 1, caractérisée en ce que dans le composé de formule générale I, tout groupe alkyl, cycloalkyl ou alcényl représenté par A ou X ou jusqu'à 6 atomes de carbone, et en ce que tout groupe aralkyl ou aryloxy représenté par A ou X a jusqu'à 10 atomes de carbone.
3. Composition selon la revendication 1 ou 2, caractérisée en ce que A représente un groupe aralkyl éventuellement substitué.
4. Composition selon la revendication 3, caractérisée en ce que A représente un groupe benzyle substitué de formule générale:
Figure imgb0018
dans laquelle Z représente un atome d'halogène ou un groupe alcoxy ayant de 1 à 4 atomes de carbone et Q représente un groupe alkyle ayant de 1 à 6 atomes de carbone.
5. Composition selon la revendication 4, caractérisée en ce que A représente un groupe alpha- isopropyl-4-chlorobenzyle, R représente un atome d'hydrogène ou un groupe cyano, n représente 1 et X représente un groupe 3-phénoxy.
6. Composition selon la revendication 5, caractérisée en ce que le composé de formule générale I est le alpha-cyano-3-phénoxy-benzyl-2-(4-chlorophényl)-3-méthylbutanoate.
7. Composition selon la revendication 1 ou 2, caractérisé en ce que A représente un groupe cyclopropyl de formule:
Figure imgb0019
dans laquelle Ra et Rb représentent chacun individuellement un groupe alkyl ayant de 1 à 6 atomes de carbone ou un atome d'halogène; ou Ra et Rb représentent ensemble un groupe alkylène ayant de 2 à 6 atomes de carbone; ou Ra représente un atome d'hydrogène et Rb représente un groupe alcényl ayant de 2 à 6 atomes de carbone et de 1 à 3 atomes de chlore ou de brome; Re et Rd représentent ensemble un groupe alkyl ayant de 1 à 6 atomes de carbone; ou Re et Rd représentent ensemble un groupe alkylène ayant de 2 à 6 atomes de carbone.
8. Procédé pour détruire les organismes nuisibles en un lieu, caractérisé en ce qu'on applique en ce lieu une composition selon l'une des revendications 1 à 7.
EP78200099A 1977-08-10 1978-07-14 Composition pesticide et procédé pour détruire les organismes nuisibles Expired EP0000962B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB3352477 1977-08-10
GB3352477 1977-08-10

Publications (2)

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EP0000962A1 EP0000962A1 (fr) 1979-03-07
EP0000962B1 true EP0000962B1 (fr) 1981-11-18

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US (1) US4182772A (fr)
EP (1) EP0000962B1 (fr)
JP (1) JPS5432625A (fr)
AU (1) AU517757B2 (fr)
BR (1) BR7805081A (fr)
DE (1) DE2861331D1 (fr)
TR (1) TR20063A (fr)
ZA (1) ZA784473B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2819788A1 (de) * 1978-05-05 1979-11-08 Bayer Ag Benzylester mit fluorsubstituierten aether- und/oder thioaethergruppen und ihre verwendung als insektizide
DE3045310C2 (de) * 1980-12-02 1983-12-01 Kuka Schweissanlagen + Roboter Gmbh, 8900 Augsburg Verfahren und Vorrichtung zum miteinander Verschweißen ferromagnetischer Werkstücke mittels umlaufendem elektrischem Lichtbogen
JPH0676281B2 (ja) * 1986-01-17 1994-09-28 住友化学工業株式会社 安定化された水中油型懸濁状農薬組成物
AU201813729S (en) 2017-12-28 2018-07-18 Wisconsin Alumni Res Found Otoscope

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IE34761B1 (en) * 1969-12-12 1975-08-06 Boots Pure Drug Co Ltd 1,3,5 - triazapenta-1,4-dienes; intermediate formamidines
JPS4861633A (fr) * 1971-12-04 1973-08-29
JPS4861630A (fr) * 1971-12-06 1973-08-29
DE2326077C2 (de) * 1972-05-25 1985-12-12 National Research Development Corp., London Ungesättigte Cyclopropancarbonsäuren und deren Derivate, deren Herstellung und diese enthaltende Insektizide
EG11383A (en) * 1972-07-11 1979-03-31 Sumitomo Chemical Co Novel composition for controlling nixious insects and process for preparing thereof
US4291056A (en) * 1975-07-28 1981-09-22 Ciba-Geigy Corporation Pesticidal esters
DE2706222A1 (de) * 1976-02-16 1977-08-18 Ciba Geigy Ag Cyclopropancarbonsaeureester, verfahren zu ihrer herstellung und ihre verwendung

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DE2861331D1 (en) 1982-01-21
JPS5432625A (en) 1979-03-10
AU3870978A (en) 1980-02-14
BR7805081A (pt) 1979-03-13
TR20063A (tr) 1980-07-07
US4182772A (en) 1980-01-08
ZA784473B (en) 1979-07-25
EP0000962A1 (fr) 1979-03-07
AU517757B2 (en) 1981-08-27

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