GB2271110A - Pesticidal imidazolidine derivatives - Google Patents

Pesticidal imidazolidine derivatives Download PDF

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Publication number
GB2271110A
GB2271110A GB9316625A GB9316625A GB2271110A GB 2271110 A GB2271110 A GB 2271110A GB 9316625 A GB9316625 A GB 9316625A GB 9316625 A GB9316625 A GB 9316625A GB 2271110 A GB2271110 A GB 2271110A
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formula
compounds
compound
radical
active ingredient
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GB9316625A
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GB9316625D0 (en
Inventor
Marc Benoit
Jean-Pierre Demoute
Pierre Pastre
Antonio Ugolini
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Sanofi Aventis France
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Roussel Uclaf SA
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Publication of GB9316625D0 publication Critical patent/GB9316625D0/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A01N47/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing >N—S—C≡(Hal)3 groups
    • 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
    • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/44—Nitrogen atoms not forming part of a nitro radical
    • C07D233/52—Nitrogen atoms not forming part of a nitro radical with hetero atoms directly attached to said nitrogen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

1 2271110 New derivatives of imidazolidine, their preparation process and
their use as pesticides The present invention relates to new derivatives of imidazolidine. their preparation process and their use as pesticides.
A subject of the invention is the compounds of formula X -NO 2 ArCH,-N N SR in which:
- Ar represents an aryl or heteroaryl radical optionally substituted by one or more substituents chosen from the group constituted by halogen atoms. linear. branched or cyclic alkyl radicals containing up to 4 carbon atoms (optionally substituted by one or more halogen atcm), and free, esterified and etherified SH and OH radicals, - X represents a nitrogen atom or a =CH- group, - R represents a linear, branched or cyclic alkyl, alkenyl or alkynyl radical containing up to 12 carbon atoms optionally substituted by one or more halogen atans, or R represents an Salk radical, alk representing an alkyl radical containing up to 4 carbon atoms optionally substituted by one or more halogen atoms.
As an aryl radical, the phenyl or naphthyl radical can be mentioned.
As a heteroaryl radical, the piperidyl radical, the pyrimidyl radical, the pyridyl radical, the thiazolyl radical, the oxazolyl radical and the morpholinyl radical can be mentioned.
When Ar is substituted by one or more halogen atoms, the halogen is preferably chlorine or bromine.
When Ar is substituted by one or more alkyl radicals, each alkyl radical is preferably the methyl, ethyl or n-propyl radical.
2 When Ar is substituted by an esterified OH or SH radical, the ester residue is preferably the acetyl, propionyl or benzoyl radical.
When Ar is substituted by an etherified OH or SH radical, the ether residue is preferably the methyl or ethyl radical.
When R represents an alkyl radical, it is preferably a methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, terbutyl, n-pentyl or n-hexyl radical, or a cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl radical.
When R represents an Salk radical,Salk preferably represents an S-methyl, S-ethyl, S-propyl, S-butyl, Sisobutyl or S-terbutyl radical.
When R is substituted by one or more halogen atoms, the halogen is preferably chlorine or bromine.
Among the preferred compounds of the invention, the compounds can be mentioned in which Ar represents an optionally substituted pyridinyl radical, for example the compounds in which Ar represents a 6-chloro 3pyridinyl radical; there can also be mentioned the compounds of formula (I) in which X represents a nitrogen atom.
In particular, a subject of the invention is also the compounds of formula (I) in which R represents a linear, branched or cyclic alkyl radical containing up to 8 carbon atoms optionally substituted by one or more halogen atoms, such as for example a terbutyl radical. or also a trichloromethyl radical. Quite especially a subject of the invention is the compounds of Examples 3 and 5A. 30 The compounds of formula (I) have useful properties which allow their use for combating parasites. It can be for example for combating parasites of vegetation, whether it be parasites of the soil or of the parts above ground, parasites of premises and parasites of warm- blooded animals. 35 Thus it is that the products of the'invention can be used to combat parasitic insects, nematodes and acaridae of vegetation and animals. In particular a subject of the invention is the use of 3 the compounds of formula (I) to combat parasites of vegetation, parasites of premises and parasites of warmblooded animals.
The products of formula (I) can also be used to combat insects in premises, in particular to combat flies. mosquitoes and cockroaches.
The products of formula (I) can also be used to combat insects and other parasites of the soil, for example Coleoptera, such as Diabrotica, click beetles and May beetle grubs, Myriapoda such as scutigeridae and blanjules, and Diptera such as cecydomia and Lepidoptera such as owlet moths.
They are preferably used at doses of between 5 g and 300 g of active ingredient per hectare.
All these properties make the products of formula (I) products which correspond perfectly-to the requirements of the modern agrochemical industry: they allow the protection of crops while preserving the environment.
The products of formula (I) can also be used to combat parasitic acaridae and nematodes of vegetation..
The compounds of formula (I) can also be used to combat parasitic acaridae of animals, to combat, for example, ticks and notably ticks of the Boophilus species, those of the Hyalomnia species, those of the Amblyomnia species and those of the Rhipicephalus species or to combat all sorts of mites and notably the sarcoptic mite, the psoroptic mite and the chorioptic mite.
Therefore a subject of the invention is the compositions intended to combat parasites of warm-blooded animals, parasites of premises and vegetation, characterized in that they contain at least one of the products of formula (I) defined above and notably the product of Example 3 or of Example 5A.
Notably a subject of the invention is the insecticide compositions containing as active ingredient at least one of the products defined above.
Also a subject of the invention is the acaricide compositions containing as active ingredient at least one of 4 the products defined above.
Also a subject of the invention is the nematicide compositions containing as active ingredient at least one of the products defined above.
Finally a subject of the invention is the acaricide compositions intended for combating parasites of warm-blooded animals, in particular for combating ticks and mites, containing at least one of the products defined above as active ingredient.
These compositions are prepared according to the usual processes of the agrochemical industry or the veterinary industry or the animal-feed products industry.
In these compositions intended for agricultural use and for use in premises, the active ingredient or ingredients can have one or more other pesticide agents added to them. These compositions can be presented in the form of powders, granules, suspensions, emulsions, solutions, aerosol solutions, combustible strips, baits or other preparations usually employed for the use of this type of compound.
In addition to the active ingredient, theseicompositions contain, in general, a vehicle andlor a non-ionic surfactant, ensuring, moreover, a uniform dispersion of the constituent substances of the mixture. The 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 combustible solid. The insecticide compositions according to the invention contain preferably 0. 005% to 10% by weight of active ingredient. 30 According to an advantageous operating method, for use in premises, the compositions according to the invention are used in the form of fumigant compositions. The compositions according to the invention can then be advantageously composed of, for the non-active part, a combustible insecticide coil, or also an incombustible fibrous substrate. In the latter case, the fumigant obtained after incorporation of the active ingredient is placed on a heating apparatus such as an electric emanator.
In the case where an insecticide coil is used, the inert support can be, for example, composed of Pyrethrum marc, Tabu powder (or Machilus Thumbergii leaf powder), Pyrethrum stem powder, cedar leaf powder, sawdust (such as pine sawdust), 5 starch and coconut shell powder.
The dose of active ingredient can then be, for example, 0.03 to 1% by weight.
In the case where an incombustible fibrous support is used, the dose of active ingredient can then be, for example, 0.03 to 95% by weight.
The compositions according to the invention for use in premises can also be obtained by preparing a sprayable oil based on the active ingredient, this oil soaking a lamp wick and then being set alight.
The concentration of active ingredient incorporated in the oil is, preferably, 0.03 to 95% by weight.
The insecticide compositions according to the invention, as acaricide and nematicide compositions, can optionally have other pesticide agents added to them. The acaricide and nematicide compositions can be presented notably.in the form of powder, granules, suspensions, emulsions, solutions.
For acaricide use, wettable powders are preferably used, for foliar spraying, containing 1 to 80% by weight of active ingredient or liquids 'for foliar spraying containing 1 to 500 g/1 of active ingredient. Powders for foliar dusting containing 0.05% to 3% of active ingredient can also be used.
For nematicide use, liquids for soil treatment containing 300 to 500 g/1 of active ingredient are preferably used.
The acaricide and nematicide compounds according to the invention are used, preferably, at doses comprised between 1 and 100 g of active ingredient per hectare.
To increase the biological activity of the products of the invention they can be added to standard synergists used in such cases, such as 1-(2,5,8-trioxadodecyl.) 2-propyl 4, 5methylenedioxy benzene (or piperonyl butoxide) or N-(2-ethyl heptyl) bicyclo [2,2,1] 5-heptene-2,3-dicarboximide, or piperonyl-bis-2-(21-n- butoxy-ethoxy) ethylacetal (or 6 tropital) The compounds of formula (I) show an excellent general tolerance, and therefore a subject of the invention is also the products of formula (I), notably for combating illnesses 5 caused by ticks and mites in humans and animals.
The products of the invention are notably used to combat lice in a preventive or curative way and to combat scabies.
The products of the invention can be administered by external route, by spraying, by shampooing, by bathing or painting on.
The products of the.invention for veterinary use can also be administered by painting the dorsal spine according to the so-called "pour-on" method.
It can also be indicated that the products of the invention can be used as biocides or as growth regulators.
Also a subject of the invention is a preparation process f or the compounds of f ormula (I), as def ined above, characterized in that a compound of formula X -NO 2 11 ArCH._ N NH in which Ar and X are defined as previously, is subjected to the action of a compound of formula (III):
RSHal in which R is defined as previously, and Hal is a halogen atom, in the presence of a base in order to obtain the corresponding compound of formula (I).
In a preferred embodiment of the process of the invention: - the compound of formula (III) is prepared" in situ 11, by the action of sulphuryl chloride on a disulphide of formula RSSR, or also by the action of chlorine on a disulphide of 7 formula RSSR, - the base used is preferably sodium hydride, an alkaline or alkaline-earth alcoholate, an alkaline amide, a secondary or tertiary amine in the presence of lithium bromide. 5 The products of formula (I1) used as starting products are described in the European Patent 192,060. The following examples illustrate the invention without however limiting it. EXAMPLE 1: 1-[(6-chloro 3-pyridinyl) methyl] N-nitro 3- [(methylethyl) thio] 2-imidazolidinimine, a) Preparation of the nethylethyl sulphide chloride 5.25 cm3 of sulphuryl chloride is introduced at -200C into 10.3 cm3 of methylethyl disulphide. The reaction mixture is heated to OOC and agitation takes place at this temperature for 1 hour 30 minutes.
The sulphur dioxide is removed under progressively reduced pressure and distilled under 43 millibars. 11 g of desired product is obtained. B.p. 43mb - 280C.
b) Condensation 2.55 g of 1-[(6-chloro 3-pyridinyl) methyl].N-nitro 2 imidazolidinimine is introduced into 40 cm3 of tetrahydrofuran. 0.48 g of sodium hydride at 50% in oil is added. Agitation is carried out for 30 minutes followed by cooling down to 500C. Then 6 cm3 of a solution containing 11 g of the product prepared above in paragraph a) in 50 cm3 of dichloromethane is introduced. The reaction mixture is maintained under agitation for 1 hour while allowing the temperature to rise to about 200C. The whole is poured into a bath of water and ice, followed by extraction with methylene chloride, drying and bringing to dryness under reduced pressure. A product is obtained which is chromatographed on silica, eluting with a methylene chloride - methanol mixture (95-5). In this way 1.75 g of desired product is obtained, melting after recrystallization from 35 ethyl acetate at 1100C.
EXAMPLE 2: 1-[(6-chloro 3-pyridinyl) methyl] N-nitro 3- [(cyclohexyl) thio] 2-imidazolidinimine a) Preparation of the cyclohexyl sulphide chloride 0.77 g of dicyclohexyl disulphide is introduced into 5 CM3 of carbon tetrachloride. The mixture is cooled down to 100C and a current of chlorine is bubbled through until 0.24 g of chlorine is fixed. Agitation is carried out for 10 minutes at -100C. In this way a solution is obtained which is used as it is for the following stage. b) Condensation 1.27 g of 1-[(6-chloro 3-pyridinyl) methyl] N-nitro 2imidazolidinimine is introduced into 20 cm3 of tetrahydrofuran. Then 0.29 g of sodium hydride in solution at.50% in oil is introduced. Agitation is carried out for 30 minutes, followed by cooling down to -200C and the solution prepared in paragraph a) is introduced over 10 minutes. Agitation is carried out for 10 minutes at - 200C and the whole is poured into 50 cm3 of a saturated aqueous solution of sodium acid carbonate. Agitation is carried out followed by extracting with methylene chloride, decanting, drying and bringing to dryness. 2.9 g of product is obtained which is chromatographed on silica, eluting with a methylene chloride - methanol mixture (95-5). The product with an Rf = 0.55 is collected. After bringing to dryness a product is obtained which is recrystallized from ethyl acetate. 1.16 g of desired product is obtained melting at 1280C. EXAMPLES 3 to 5: by operating as previously, the following products were obtained: Example-3: 1.-[(6-chloro 3-pyridinyl) methyl] N- nitro 3[(trichloromethyl) thiol 2-imidazolidinizine M.p. = 1370C Example 4: 1-[(6-chloro 3-pyridinyl) methyl] N-nitro 3-(l- methyl) propylthio] 2-imidazolidinimine M.p. = 1160C Example 5: 1-[(6- chloro 3-pyridinyl) methyl] 3-[(1,1dimethylethyl) dithio] N-nitro 2- imidazolidinimine (product B) and 1-[(6-chloro 3-pyridinyl) methyl] 3-[(1, 1-dimethyl ethyl) thio] N-nitro 2-imidazolidinimine (product A). a) Preparation of the 1,1-dimethylethyl sulphide chloride.
0.59 g of diterbutyl disulphide is introduced into 5 cm3 of carbon tetrachloride. The mixture is cooled down to -100C 9 and a current of chlorine is bubbled through until 0.24 g of chlorine is fixed. Then agitation is carried out for 10 minutes at -100C. A solution is obtained which is used as it is.
b) Condensat ion.
1.27 g of 1-[(6-chloro 3-pyridinyl) methyl] N-nitro 2imidazolidinimine is introduced into 20 cm3 of tetrahydrofuran. Then 0.29 g of sodium hydride at 50% in oil is introduced. The solution obtained is agitated for 30 minutes, cooled down to -200C and the 1,1-dimethylethyl sulphide chloride solution obtained in Stage a) is introduced. Agitation is carried out for 20 minutes at -200C and the whole is poured into a saturated aqueous solution of sodium acid carbonate, followed by agitating, extracting with methyl chloride, decanting, drying and bringing to dryness. 1.8 g of product is obtained which is chromatographed on silica eluting with a methylene chloride - methanol mixture (95-5). 0.7 g of product B, Rf = 0. 60, M.p. = 1340C and 0.8 g of a product with Rf = 0.35 are obtained, followed bychromatography on silica eluting with a methylene chloride ethyl acetate mixture (7-3). The product with Rf = 0.25 is isolated. 180 mg of product A is obtained. M.p. = 1410C.
Study of the activitv of the compounds of the invention a) Study of the activity on Aphis craccivora Bean plants are treated by soaking the leaves in a hydroacetonic solution of the active ingredient (50% acetone, 50% water) then dried under a ventilated hood.
The leaves are then infested: 20 female Aphis craccivora adults per leaf and maintained at 220C under an illuminated ceiling.
Mortality checks are carried out after 48 hours.
Results: Starting at a dose of 20 ppm, the products have a useful aphicide activity. b) Study of the effect on Spodoptera littoralis larvae by contact and ingestion.
L3 stage larva of Spodoptera littoralis are used. The operation takes place at 220C under relative humidity conditions of 50%. PETRI dishes are used containing a circle of damp filter paper, two bean leaves treated with a hydroacetonic solution (50-50) containing the product to be 5 tested are placed in each dish.
The number of dead larva are counted after 7 days. c) Study of the effect on Phaedon cochleariae.
The operation takes place at 220C under relative humidity conditions of 50%. PETRI dishes containing a circle of damp filter paper and two disks of chinese cabbage leaves treated with a hydroaco-tonic solution (50-50) containing the product to be tested are used.
The number of dead insects are counted after one week.
The products of the invention have a useful activity on Spodoptera littoralis and Phaedon cochleariae.

Claims (1)

1) The compounds of formula (I):
X - N02 ArCH2- N N - SR in which: - Ar represents an aryl or heteroaryl radical optionally substituted by one or more substituents chosen from the group constituted by halogen atoms, linear, branched or cyclic alkyl radicals containing up to 4 carbon atoms (optionally substituted by one or more halogen atcms), and free, esterified and etherified SH and OH radicals, - X represents a nitrogen atom or a =CH- group, and - R represents a linear, branched or cyclic alkyl, alkenyl or alkynyl radical containing up to 12 carbon atoms optionally substituted by one or more halogen atcos, or R represents an Salk radical alk representing an alkyl radical containing up to 4 carbon atoms optionally substituted by one or more halogen atoms. 2) The compounds of formula (I) as defined in claim 1,in which Ar represents an optionally substituted pyridinyl radical.
3) The compounds of formula (I) as defined in claim 2, in which Ar represents a 6-chloro 3-pyridinyl radical. 4) The compounds of formula (I) as defined in any one of claims 1 to 3 in which X represents a nitrogen atom. 5) The compounds of formula (I) as defined in any one of claims 1 to 4 in which R represents a linear, branched or cyclic alkyl radical containing up to 8 carbon atoms optionally substituted by one or more halogen atoms.
6) The compounds of formula (I) as defined in claim 5 in which R represents a terbutyl radical. 7) The compounds of formula (I) as defined in claim 5 in which R represents a trichloromethyl radical.
12 8) The compounds of formula (I) as defined in claim 1 the names of which follow: - 1-[(6-chloro 3-pyridinyl) methyl] N-nitro 3-[(trichloromethyl) thio] 2-imidazolidinimine, - 1-[(6-chloro 3-pyridinyl) methyl] N-nitro 3-[(1,1-dimethylethyl) thio] 2-imidazolidinizine. 9) The compositions intended to combat parasites of vegetation, parasites of premises and parasites of warmblooded animals, characterized in that they contain at least one of the compounds def ined in any one of claims 1 to 7 as active ingredient. 10) The compositions intended to combat parasites of vegetation, parasites of premises and parasites of warmblooded animals, characterized in that they contain at least one of the compounds defined in claim 8 as active ingredient. 11) The insecticidal compositions containing at least one of the compounds def ined in any one of claims 1 to 8 as active ingredient.
12) The acaricidal compositions containing at least one of the compounds def ined in any one of claims 1 to 8 as active ingredient. 13) The nematicidal compositions containing at least one of the compounds def ined in any one of claims 1 to 8 as active ingredient.
14) A composition as claimed in claim 11 containing 0.005% to 10% by weight of active ingredient.
15) A composition as claimed in claim 9 or claim 10 in the form of a fumigant composition.
16) A compound of formula (I) as defined in any one of claims 1 to 8 for use in therapy.
17) Use of a compound of formula (I) as defined in any one of claims 1 to 8 for the preparation of a composition for combating parasites of warmblooded animals.
18) Use of a compound of formula (I) as defined in any one of claims 1 to 8 as an insecticide.
19) Use of a compound of formula (I) as defined in any one of claims 1 to 8 as an acaricide.
20) Use of a compound of formula (I) as defined in any one of claims 1 to 8 as a nematicide.
21) Use as claimed in claim 18 comprising administering to a locus between 5g and 300g of active ingredient per hectare.
22) Use as claimed in claim 19 or claim 20 comprising administering to a locus between lg and 100g of active ingredient per hectare.
23) A process for preparing a compound of formula (I) as defined in any one of claims 1 to 8, wherein a compound of formula (II) X-N02 ArCH2-N NH in which Ar and X are as defined in claim 1, is reacted with a compound of formula (III) RSHal (III) in which Hal is a halogen atom and R is as defined in claim 1, in the presence of a base, in order to obtain the corresponding compound of formula (I).
24) A process as claimed in claim 23 wherein the compound of formula (III) is prepared in situ by the action of chlorine or of sulphuryl chloride on a disulphide of formula RSSR wherein R is as defined in claim 1.
25) A process as claimed in claim 23 or claim 24 wherein the base used is sodium hydride, an alkaline or alkaline-earth alcoholate, an alkaline amide, or a secondary or tertiary amine in the presence of lithium bromide.
26) A compound of formula (I) as specifically disclosed herein in any one of the Examples.
27) A process for the preparation of a compound of formula (I) substantially as described herein in any one of the Examples.
GB9316625A 1992-08-11 1993-08-10 Pesticidal imidazolidine derivatives Withdrawn GB2271110A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR9209905A FR2694752B1 (en) 1992-08-11 1992-08-11 New imidazole derivatives, their preparation process and their application as pesticides.

Publications (2)

Publication Number Publication Date
GB9316625D0 GB9316625D0 (en) 1993-09-29
GB2271110A true GB2271110A (en) 1994-04-06

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GB9316625A Withdrawn GB2271110A (en) 1992-08-11 1993-08-10 Pesticidal imidazolidine derivatives

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EP (1) EP0583198A1 (en)
JP (1) JPH06263741A (en)
DE (1) DE4326983A1 (en)
FR (1) FR2694752B1 (en)
GB (1) GB2271110A (en)
IT (1) IT1261512B (en)
NL (1) NL9301392A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6232328B1 (en) 1994-05-20 2001-05-15 Bayer Aktiengesellschaft Non-systemic control of parasites
CN106892846A (en) * 2015-12-18 2017-06-27 中国石油化工股份有限公司 A kind of method for preparing cyclohexyl time sulfonic acid chloride

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0192060A1 (en) * 1985-02-04 1986-08-27 Nihon Bayer Agrochem K.K. Heterocyclic compounds
EP0277317A1 (en) * 1986-12-19 1988-08-10 Nihon Tokushu Noyaku Seizo K.K. Nitro derivatives of 2-iminoimidazolidines and 2-iminotetrahydropyrimidines
EP0285985A1 (en) * 1987-04-10 1988-10-12 Bayer Ag 3-Substituted 1-(2-chlorothiazol-5-yl-methyl)-2-nitroimino-1,3-diazacycloalkanes

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH049371A (en) * 1990-04-25 1992-01-14 Ishihara Sangyo Kaisha Ltd Nitroimino-based compound, production thereof and pest-controlling agent containing same compound

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0192060A1 (en) * 1985-02-04 1986-08-27 Nihon Bayer Agrochem K.K. Heterocyclic compounds
EP0277317A1 (en) * 1986-12-19 1988-08-10 Nihon Tokushu Noyaku Seizo K.K. Nitro derivatives of 2-iminoimidazolidines and 2-iminotetrahydropyrimidines
EP0285985A1 (en) * 1987-04-10 1988-10-12 Bayer Ag 3-Substituted 1-(2-chlorothiazol-5-yl-methyl)-2-nitroimino-1,3-diazacycloalkanes

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6232328B1 (en) 1994-05-20 2001-05-15 Bayer Aktiengesellschaft Non-systemic control of parasites
US6329374B1 (en) 1994-05-20 2001-12-11 Bayer Aktiengesellschaft Non-systemic control of parasites
US6429206B2 (en) 1994-05-20 2002-08-06 Bayer Aktiengesellschaft Non-systemic control of parasites
US6495573B2 (en) 1994-05-20 2002-12-17 Bayer Aktiengesellschaft Non-systemic control of parasites
US6613783B2 (en) 1994-05-20 2003-09-02 Bayer Aktiengesellschaft Non-systemic control of parasites
US6896891B2 (en) 1994-05-20 2005-05-24 Bayer Aktiengesellschaft Non-systemic control of parasites
US7517535B2 (en) 1994-05-20 2009-04-14 Bayer Animal Health Gmbh Non-systemic control of parasites
US8728507B2 (en) 1994-05-20 2014-05-20 Bayer Intellectual Property Gmbh Non-systemic control of parasites
CN106892846A (en) * 2015-12-18 2017-06-27 中国石油化工股份有限公司 A kind of method for preparing cyclohexyl time sulfonic acid chloride

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EP0583198A1 (en) 1994-02-16
DE4326983A1 (en) 1994-02-17
JPH06263741A (en) 1994-09-20
ITRM930546A1 (en) 1995-02-09
GB9316625D0 (en) 1993-09-29
NL9301392A (en) 1994-03-01
FR2694752A1 (en) 1994-02-18
ITRM930546A0 (en) 1993-08-09
FR2694752B1 (en) 1994-10-14
IT1261512B (en) 1996-05-23

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