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
  • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C255/00—Carboxylic acid nitriles
  • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
  • C07C255/31—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing rings other than six-membered aromatic rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
  • C07C33/40—Halogenated unsaturated alcohols
  • C07C33/46—Halogenated unsaturated alcohols containing only six-membered aromatic rings as cyclic parts
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
  • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
  • C07C69/743—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of acids with a three-membered ring and with unsaturation outside the ring
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C2601/00—Systems containing only non-condensed rings
  • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

Definitions

• the present invention relates to new pyre ⁇ thrinoid esters of 4- (dihalomethyl) 2,3,5,6-tetrafluorobenzyl alcohol, their preparation process and their application as pesticides.
• the subject of the invention is the compounds of formula (I):
• Hal 2 identical or different from each other, represent a halogen atom
• - X represents a hydrogen atom, an alkyl radical, alké- nyle or alkynyl containing up to 4 carbon atoms or a cyano radical or an aralkynyl radical containing up to 1 0 carbon atoms,
• Hal., And Hal- preferably represent a fluorine, chlorine or bromine atom.
• X represents an alkyl radical, it is preferably a methyl radical.
• Ha 2 and Hal 2 represent the same halogen atom, for example those in which Hal j and Ha 1 , each represent a fluorine atom.
• a more particular subject of the invention is the compounds of formula (I) as defined above, in which: either A represents a radical:
• Z j _ represents a hydrogen atom
• Z 3 represents a hydrogen or halogen atom and T ⁇ and T 2 , which are identical or different, represent a hydrogen atom, a halogen atom, an alkyloxy or alkyl radical containing from 1 to 8 atoms carbon optionally substituted by halogens, a mono-, di- or tri-fluoromethyl or cyano radical or a phenyl ring optionally substituted by a halogen, or T 1 and T 2 together form a cycloalkyl radical containing 3 to 6 carbon atoms or a radical:
• D represents a hydrogen or halogen atom, an alkyloxy radical containing from 1 to 8 carbon atoms
• G represents an oxygen or sulfur atom
• J represents either a linear, branched or cyclic alkyl radical , saturated or unsaturated, containing from 1 to 8 carbon atoms, optionally substituted by one or more functional groups, identical or different, or else an aryl group containing from 6 to 14 carbon atoms, optionally substituted by one or more functional groups identi ⁇ that or different, or else a heterocyclic radical possibly substituted by one or more functional groups, identical or different, or else A represents a radical:
• U in any position on the benzene ring, represents a halogen atom, an alkyl radical containing from 1 to 8 carbon atoms or an alkoxy radical containing from 1 to 8 carbon atoms, m representing the number 0, 1 or 2 and when m is 2, the substituents U can be the same or different.
• T 2 or 1- represent a halogen atom, it it is preferably a fluorine, chlorine or bromine atom.
• ⁇ or T 2 represents an alkyl or alky ⁇ loxy radical, it is preferably a methyl, ethyl, propyl, methoxy, ethoxy or propoxy radical.
• a, b, c and d preferably represent a chlorine or bromine atom.
• alkyl is preferably understood to mean a radical containing from 1 to 8 carbon atoms such as, for example, the methyl, ethyl, propyl, isopropyl, butyl or isobutyl radical. or tert-butyl and by functional group one of those mentioned in the European application published under the number 50534.
• J can also represent an alkyl radical substituted by an aryl radical, in particular an optionally substituted phenyl radical.
• aryl radical in particular an optionally substituted phenyl radical.
• J represents an alkyl radical substituted by one or more functional groups, there may be mentioned as preferred values of J, the radicals:
• n 1 is an integer from 1 to S and Hal ⁇ n halogen atom, for example the radical -CH 2 -CC1 3 , -CH 2 -CF 3 , - CH 2 -CH 2 -CC1 3 or CH 2 -CH 2 -CF 3 ;
• n 2 is a number from 0 to 8, for example the radical -CH 2 -CHC1 2 , -CH 2 -CHF 2 or -CHF 2 ; - (CH 2 ) n -CH 2 (Hal) in which n 1 and Hal are defined as above, for example the radical -CH 2 -CH 2 C1 or -CH 2 -CH 2 F, -C (CHal 3 ) 3 in which Hal is defined as above, for example the radical -C (CF 3 ) 3 or -C (CF 3 ) 2 ⁇ CC1 3 , -C (CF 3 ) 2 -CH 3 , -C (CH 3 ) 2 -CF 3 or -C (CH 3 ) (CF 3 ) -CH 2 -CK 3 , -CH (CF 3 ) -CH 3 or -CH (CF 3 ) 2 , -C (CH 3 ) 2 in which Hal is defined as above and n 2 -CH 2 C1 or -CH
• n ⁇ and R a are defined as above and the two radicals R a can be different from each other, for example the radical:
• n ⁇ is defined as above for example the radical
• n ⁇ ⁇ is defined as above, for example the benzyl or phenethyl radical
• n ⁇ is defined as above, for example the radical:
• J represents an optionally substituted aryl radical, it is preferably the optionally substituted phenyl radical.
• J represents a heterocyclic radical
• they are preferably pyridyl, furyl, thienyl, oxazolyl or thiazolyl radicals.
• Hal represents a halogen atom and J represents t an alkyl radical containing from 1 to 8 carbon atoms, linear, branched or cyclized and saturated, optionally substituted by one or more halogen atoms, the double bond having the geometry (E), for example those in which Hal represents a fluorine atom and J a linear or branched alkyl radical containing up to 4 carbon atoms.
• A represents a radical:
• ⁇ represents a bromine or chlorine atom.
• Z 1 and Z 2 each represent a methyl radical.
• Z 1 and Z 2 each represent a methyl radical.
• the subject of the invention is of course more particularly of course the compounds the preparation of which is given below in the experimental part, such as the compound of Example 1 or also the compounds of Examples 3, 4 and 5.
• a subject of the invention is also a process for preparation, characterized in that an acid of formula (II) is subjected:
• the functional acid derivative used is preferably an acid chloride.
• the acids of formula (II) used are known products, used in the synthesis of pyrethroid compounds.
• the alcohols of formula (III) are new products and are themselves an object of the present invention.
• alcohols of formula (III) there may be mentioned as preferred alcohol, the alcohol the preparation of which is given below in the experimental part.
• the alcohols of formula (III) can be prepared by analogy with the process for the preparation of 4-difluo ⁇ romethyl 2,3,5,6-tetrafluorobenzyl alcohol described below in the experimental part which can be schematized as follows:
• THP 2-tetrahydropyrannyl
• the compounds of formula (I) have interesting properties which allow their use in the fight against parasites. It can be, for example, the fight against plant parasites, whether they are soil parasites or aerial parts, local parasites and parasites of warm-blooded animals.
• the subject of the invention is in particular the application of the compounds of formula (I) to the fight against plant parasites, local parasites and parasites of warm-blooded animals.
• the products of formula (I) can also be used to fight against insects and other soil parasites, for example beetles, such as DIABROTICA, wireworms and white worms, myriapods such as scutigeria and blaniules, and dipterans as cécydoi ⁇ i ⁇ s and lepidoptera like the ground moths. They are used in doses of between 5 g and 300 g of active ingredient per hectare.
• the products of formula (I) can also be used to fight against insects in premises, to fight in particular against flies, mosquitoes and cockroaches.
• the products of formula (I) are more photostable.
• the products of formula (I) can also be used to fight against mites and parasitic nematodes of plants.
• the compounds of formula (I) can also be used to fight against parasitic mites of animals, to fight for example against ticks and in particular ticks of the genus Boophilus, those of the genus Hyalomnia, those of the genus Amblyomnia and those of the genus Rhipicephalus or to fight against all kinds of scabies, in particular sarcoptic scabies, psoroptic scabies and chorioptic scabies.
• a subject of the invention is therefore also compositions intended for combating parasites of warm-blooded animals, parasites of premises and plants, characterized in that they contain at least one of the products of the formula ( I) defined above and in particular the product of example 1 or else the products of examples 3, 4 and 5.
• the invention particularly relates to insecticide compositions containing as active principle at least one of the products defined above.
• compositions according to the invention are prepared according to the usual methods of the agrochemical industry or of the veterinary industry or of the industry for products intended for animal nutrition. These compositions can be in the form of powders, granules, suspensions, emulsions, solutions, solutions for aerosols, combustible strips, baits or other preparations conventionally used for the use of this. kind of compounds.
• these compositions generally contain a vehicle and / or a non-ionic surfactant, ensuring, moreover, a uniform dispersion of the constituent substances of the mixture.
• vehicle 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, clays, silicates, kieselguhr or a solid fuel.
• 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 compositions.
• compositions according to the invention can then advantageously consist, for the non-active part, of a combustible insecticide coil (or coil), or also of an incombustible fibrous substrate.
• a heating device such as an electric emitter.
• the inert support can be, for example, composed of pyrethrum marc, Tabu powder (or Machilus Thumbergii leaf powder), pyrethrum stem powder, cedar leaf powder , wood powder (such as sawdust) starch and coconut shell powder.
• the dose of active ingredient can then 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 premises can also be obtained by preparing a sprayable oil based on active principle, this oil soaking the wick of a lamp and then being subjected to combustion.
• the concentration of the active ingredient incorporated in the oil is preferably from 0.03 to 95% by weight.
• the subject of the invention is also the acaricidal compositions containing as active principle at least one of the products of formula (I) defined above.
• a subject of the invention is also the nematicide compositions containing as active principle at least one of the products of formula (I) defined above.
• the insecticide compositions according to the invention can optionally be added with one or more other pesticidal agents.
• the acaricide and nematicide compositions can be in particular in the form of powder, granules, suspen ⁇ sions, emulsions, solutions.
• wettable powders are preferably used for foliar spraying, containing from 1 to 80% by weight of active ingredient, or liquids for foliar spraying containing from 1 to 500 g / l of active principle. It is also possible to use powders for leaf dusting containing from 0.05 to 3% of active material.
• liquids are preferably used for treating soils containing 300 to 500 g / l of active ingredient.
• the acaricide and nematicide compounds according to the invention are preferably used in doses of between 1 and 100 g of active ingredient per hectare.
• a subject of the invention is also the acaricide compositions intended for the fight against parasitic mites of warm-blooded animals in particular against ticks and scabies, characterized in that they contain as active principle, at least one of the products of formula (I) defined above.
• the compounds of formula (I) exhibit excellent general tolerance, and the invention therefore also relates to the products of formula (I), in particular for combating the diseases created by ticks and scabies in humans and animals.
• the products of the invention are especially used to fight against lice as a preventive or curative and to fight against scabies.
• the products of the invention can be administered externally, by spraying, by shampooing, by bathing or brushing.
• the products of the invention for veterinary use can also be administered by brushing the backbone according to the method known as the "pour-on" method.
• products of the invention can be used as biocides or as growth regulators.
• the invention also relates to associations with insecticidal, acaricidal or nematicidal activity, characterized in that they contain as active material, on the one hand at least one of the compounds of general formula (I), and on the other hand, at least one of the pyrethroid esters chosen from the group consisting of esters of 1 allethrolone, of 3,4,5,6-tetrahydrophthalimidomethyl alcohol, of 5-benzyl 3-furyl methyl alcohol, of 3-phenoxy benzyl alcohol and alpha-cyano 3-phenoxy benzyl alcohol of chrysanthemic acids, by 5-benzyl 3-furyl methyl alcohol esters of 2,2-dimethyl 3- (2-oxo 3-tetrahydrothiophenylidene acids) methyl) cyclopropanecarboxylic, by esters of 3-phenoxy benzyl alcohol and alpha-cyano 3-phenoxy benzyl alcohol esters of 2,2-dimethyl 3- (2,2-dichlorovinyl)
• EXAMPLE 1 [1R, (lalpha, 3alpha)] -3 - [(Z) -2-chloro 3,3,3- (tri-fluoro 1-propenyl] 2,2-dimethyl cyclopropanecarboxylate of 4- (difluoromethyl) 2 , 3,5,6-tetrafluoro benzyl.
• Stage B alcohol 4- (difluoromethyl) 2,3,5,6-tetrafluoro benzyl
• test insects are 4-day-old female house flies.
• the operation is carried out by direct spraying at a concentration of 0.10 g / l in a Kearns and March chamber using as solvent a mixture of acetone (5%) and Isopa: L (petroleum solvent) (amount of solvent used 2 cm 3 in one second). 50 insects are used per treatment.
• the checks are carried out every minute up to 10 minutes, then at 15 minutes and the KT 50 is determined by the usual methods.
• the experimental results obtained are summarized in the following table:
• Example 4 2.2 [Example 5 6.1 B. Study of the lethal effect of the compounds of the invention on various insect worms a) Study of the lethal effect on larvae of Spodoptera Littoralis The tests are carried out by topical application of an acetone solution using the micro Arnold's manipulator on the dorsal thorax of the larvae. 15 larvae are used per back of product to be tested. The larvae used are fourth instar larvae, that is to say about 10 days old when raised at 24 ° C and 65% relative humidity. After treatment, the individuals are placed on artificial nutrient medium (Poitout medium).
• Poitout medium artificial nutrient medium
• test insects are last instar larvae of
• the lethal dose 100 (DL 1Q0 ) expressed in mg / liter is determined.

Landscapes

• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• 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)

Applications Claiming Priority (2)

Publications (1)

Family

ID=9400834

Family Applications (1)

Country Status (4)

Family Cites Families (2)

• 1990
  • 1990-10-02 FR FR9012104A patent/FR2667313B1/fr not_active Expired - Fee Related
• 1991
  • 1991-10-01 WO PCT/FR1991/000769 patent/WO1992006065A1/fr not_active Application Discontinuation
  • 1991-10-01 JP JP3516430A patent/JPH05502896A/ja active Pending
  • 1991-10-01 EP EP91919212A patent/EP0502183A1/de not_active Withdrawn

Non-Patent Citations (1)

Also Published As

Similar Documents

Legal Events