EP0000962A1 - 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
EP0000962A1
EP0000962A1 EP78200099A EP78200099A EP0000962A1 EP 0000962 A1 EP0000962 A1 EP 0000962A1 EP 78200099 A EP78200099 A EP 78200099A EP 78200099 A EP78200099 A EP 78200099A EP 0000962 A1 EP0000962 A1 EP 0000962A1
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EP
European Patent Office
Prior art keywords
group
carbon atoms
alkyl
composition
composition according
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.)
Granted
Application number
EP78200099A
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German (de)
English (en)
Other versions
EP0000962B1 (fr
Inventor
John Stewart Badmin
Robert John Knight
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.)
SHELL INT RESEARCH
Shell Internationale Research Maatschappij BV
Original Assignee
SHELL INT RESEARCH
Shell Internationale Research Maatschappij BV
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Publication of EP0000962A1 publication Critical patent/EP0000962A1/fr
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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 pyrethroid 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 a pyrethroid 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.
  • the pyrethroid insecticide I can exist in the form of optical isomers or cis-trans-isomers and in the composition according to the invention an individual isomer or mixture of isomers including racemates may be employed.
  • A represents an optionally-substituted aralkyl group in general formula I.
  • 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 alpha-isopropyl-4-chlorophenyl acetate.
  • 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 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 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 carbon atoms, especially a methyl group, or R and R d together represent an alkylene group having
  • the mixture of amitraz and the pyrethroid insecticide not only produces a pesticide having a markedly wider spectrum of activity than the pyrethroid 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 pyrethroid insecticide 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,
  • 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, 0-10%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 s-25%w active ingredient and 0-10%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, co-solvent, 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, 0.1-10%w of suspending agent, for example protective colloid and for a thixotropic agent, and 0-10%w of 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 "mayonaise"-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 coefficient
  • 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 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.

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)
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)

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

Family

ID=10354087

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78200099A Expired EP0000962B1 (fr) 1977-08-10 1978-07-14 Composition pesticide et procédé pour détruire les organismes nuisibles

Country Status (8)

Country Link
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)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4871766A (en) * 1986-01-17 1989-10-03 Sumitomo Chemical Company, Limited Oil-in-water pesticidal emulsion
WO2019133496A2 (fr) 2017-12-28 2019-07-04 Wisconsin Alumni Research Foundation Otoscope ayant un affichage électronique à faible obstruction

Families Citing this family (2)

* 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

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL7018036A (fr) * 1969-12-12 1971-06-15
NL7307130A (fr) * 1972-05-25 1973-11-27
NL7608375A (nl) * 1975-07-28 1977-02-01 Ciba Geigy Werkwijze voor het bereiden van nieuwe esters.
FR2340925A1 (fr) * 1976-02-16 1977-09-09 Ciba Geigy Ag Nouveaux esters d'acides cyclopropanecarboxyliques, leur preparation et leur application a la lutte contre les parasites

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4861633A (fr) * 1971-12-04 1973-08-29
JPS4861630A (fr) * 1971-12-06 1973-08-29
EG11383A (en) * 1972-07-11 1979-03-31 Sumitomo Chemical Co Novel composition for controlling nixious insects and process for preparing thereof

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL7018036A (fr) * 1969-12-12 1971-06-15
NL7307130A (fr) * 1972-05-25 1973-11-27
NL7608375A (nl) * 1975-07-28 1977-02-01 Ciba Geigy Werkwijze voor het bereiden van nieuwe esters.
FR2340925A1 (fr) * 1976-02-16 1977-09-09 Ciba Geigy Ag Nouveaux esters d'acides cyclopropanecarboxyliques, leur preparation et leur application a la lutte contre les parasites

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4871766A (en) * 1986-01-17 1989-10-03 Sumitomo Chemical Company, Limited Oil-in-water pesticidal emulsion
WO2019133496A2 (fr) 2017-12-28 2019-07-04 Wisconsin Alumni Research Foundation Otoscope ayant un affichage électronique à faible obstruction

Also Published As

Publication number Publication date
AU517757B2 (en) 1981-08-27
JPS5432625A (en) 1979-03-10
BR7805081A (pt) 1979-03-13
TR20063A (tr) 1980-07-07
EP0000962B1 (fr) 1981-11-18
DE2861331D1 (en) 1982-01-21
US4182772A (en) 1980-01-08
ZA784473B (en) 1979-07-25
AU3870978A (en) 1980-02-14

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