CA2148612C - 2-fluoroalkyl-substituted benzimidazoles, their preparation and their use as pesticides - Google Patents

2-fluoroalkyl-substituted benzimidazoles, their preparation and their use as pesticides Download PDF

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CA2148612C
CA2148612C CA002148612A CA2148612A CA2148612C CA 2148612 C CA2148612 C CA 2148612C CA 002148612 A CA002148612 A CA 002148612A CA 2148612 A CA2148612 A CA 2148612A CA 2148612 C CA2148612 C CA 2148612C
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carbon atoms
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lea29088
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nmr
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CA2148612A1 (en
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Winfried Lunkenheimer
Bernd Baasner
Folker Lieb
Stefan Bohm
Albrecht Marhold
Ulrich Gorgens
Wilhelm Stendel
Heinz-Wilhelm Dehne
Hans-Joachim Santel
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Bayer AG
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    • 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
    • A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • 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
    • A01N47/08—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 one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic 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
    • 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
    • A01N47/08—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 one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic 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
    • 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
    • A01N47/08—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 one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/20—N-Aryl derivatives thereof
    • 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
    • A01N47/08—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 one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
    • 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
    • A01N47/08—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 one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/10—Radicals substituted by halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
    • C07F9/6503—Five-membered rings
    • C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3
    • C07F9/65068—Five-membered rings having the nitrogen atoms in positions 1 and 3 condensed with carbocyclic rings or carbocyclic ring systems

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

Abstract

The invention relates to new substituted benzimidazoles of the general formula (I)

Description

16I t.E . P4N-+M T H i; 4Meid$MID
1'E'1CT7R A N S LAT 1 O N
Substihtted benzimidazoles The invention relates to new substituted benzimidazoles, to a plurality of processes for their preparation, and to their use as pesticides.
It has been disclosed that certain phosphoric esters or carbamates, such as, for example, the compound O,S-dimethyl-thiolo-phosphoramide or the compound O-(2-isopropoxypherryl) N-methyl-carbamate, have insecticidal properties (cf., for example, DE 1,210,835 or D:E 1,108,202).
However, the level, or duration, of action of these previously known compounds is not entirely satisfactory in all fields of application, in particular in the case of certain insects or when low concentrations are applied.

New substituted ben;dmidazoles of the general formula (I) x z X ~ N
3' / ~--R3 X N

X I I
R
in which R' represents hydrogen, alkyl, alkoxy or optionally substituted aryl, R2 represents hydroxyl, cyano or in each case optionally substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, amino, aminoc:arbonyl(-CONH2), alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, dialkoxyphosphonyl, (hetero)aryl, (hetero)arylcarbonyl, (hetero)aryloxy-Le A 29 088-PCT

carbonyl, (hetero)arylcarbonyloxy or (hetero)aryl-aminocarbonylaminocarbonyloxy, R3 represents fluoroalkyl, Xl, x2, X3 and X4 independently of one another in each case represent hydrogen, halogen, cyano, nitro, in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or cycloalkyl, optionally substituted, fused dioxyalkylene, or represent hydroxycarbonyl, alkylcarbonyl, alkoxycarbonyl or cycloalkyloxycarbonyl, in each case optionally substituted amino or aminocarbonyl or in each case optionally substituted aryl, aryloxy, arylthio, arylsulphinyl, arylsulphonyl, arylsulphonyloxy, arylcarbonyl, aryloxycarbonyl, arylazo or arylthiomethylsulphonyl, but where at least one of the substituents X1, X2, X3 or X4 represents halogenoalkyl, with the exception of the chloromethyl radical, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl, halogenoalkylsulphonyl or alkylsulphonyl, optionally substituted, fused dioxyalkylene, or represent hydroxycarbonyl, alkylcarbonyl, alkoxycarbonyl or cycloalkyloxycarbonyl, in each case optionally substituted amino or aminocarbonyl, or in each case optionally substituted aryl, arylthio, arylsulphinyl, arylsulphonyl, arylsulphonyloxy, arylcarbonyl, aryloxycarbonyl, arylazo or arylthiomethylsulphonyl, have been found.

In one aspect, the invention provides a benzimidazole of the general formula:
X
XZ
N (I) X3 ~ N

wherein:

Rl is hydrogen or C1-C8-alkyl;

R2 is CN, C1-C8-alkoxy or a substituted amino group substituted by C1-Ce-alkyl, carbo-C1-C4-alkoxy or a mixture thereof;

R3 is CF3;

X1, X2, X3 and X4, independently of each other, are hydrogen, halogen, C1-C6-halogenoalkyl, C1-C6-halogenoalkoxy, or X2 and X3 together form -O-CFCl-CFCl-O-, provided that X1, X2, X3 or X4 represents a C1-C6-halogenoalkyl group.

The compounds of the formula (I) may optionally be present in the form of geometric and/or optical isomers or regioisomers or their isomer mixtures in varying composition, depending on the nature and number of the substituents. The invention claims the pure isomers and the isomer mixtures.

Furthermore, it has been found that the new substituted benzimidazoles of the - 2a -4~~12 general formula (I) x z X ~ N
3~' ~}-- R3 (1) ~
X I I
R
in which R' represents hydrogen, alkyl, alkoxy or optionally substituted aryl, R2 represents hydroxyl, cy,ano or in each case optionally substituted alkyl, alkenyl, allcinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, amino, aminocarbonyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, dialkoxyphosphonyl, (hetero)aryl, (hetero)arylcarbonyl, (hetero)aryloxrycarbonyl, (hetero)arylcarbonyloxy or (hetero)arylamino-carbonylaminocarbonyloxy, R3 represents fluoroalkyl, X', X2, X3 and V independently of one another in each case represent hydrogen, halogen, cyano, nitro, in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or cycloalkyl, optionally substituted, fused dioxyalkylene, or represent hydroxycarbonyl, alkylcarbonyl, alkoxycarbonyl or cycloalkyloxycarbonyl, in each case optionally substituted amino or aminocarbonyl or in each case optionally substituted aryl, aryloxy, arylthio, arylsulphinyl, arylsulphonyl, aryl-sulphonylox.y, arylcarbonyl, aryloxycarbonyl, arylazo or arylthiomethy lsulphonyl, but where at least one of the substituents X', LeA29088 -3-~148 612 X3 or V represents halogenoallcyl, with the exception of the chloromethyl radical, halogenoalkoxy, halogenoalkylthio, halogenoallcylsulphinyl, halogenoalkylsulphonyl or alkylsulphonyl, optionally substituted, fused dioxyalkylene, or represent hydroxycarbonyl, alkylcarbonyl, alkoxycarbonyl or cycloalkyloxycarbonyl, in each case optionally substituted amino or aminocarbonvl, or in each case optionally substituted aryl, arylthio, arylsulphinyl, arylsulphonyl, arylsulphonyloxy, arylcarbonyl, aryloxycarbonyl, arylazo or arylthiomethylsulphonyl, are obtained when a) 1 H-benzimidazoles of the formula (II), x z is X \ N R 3 s~ I
X ~ N
a H
X
in which X3 and V have the abovementioned meaning, are reacted with compounds of the formula (III), R
A-CH
z R

in which L.eA29088 -4-A represents a suitable leaving group, R' has the abovemeritione,d meaning and R2 has the abovementioned meaning, if appropriate in the presence of a diluent and, if appropriate, in the presence of a reaction auxiliary.

Finally, it has been found that the new substituted benzimidazoles of the general formula (I) have a good activity against pests.

Surprisingly, the substituted benzimidazoles of the general formula (I) according to the invention show a considerably better insecticidal activity compared with the.
phosphoric esters or carbamates knovvn- from the prior -art, such as, for example, the compound O, S-dimethyl-thiolo-phosphoramide or the compound 0~(2-isopropoxyphenyl) N-methyl-carbamate, which are compounds with a similar action.

Formula (I) provides a general defnzition of the substituted benzimidazoles according to the invention. Preferred compounds of the forrnula (I) are those in which R' represents hydrogen, in each case straight-chain or branched alkyl or alkoxy, each of which has 1 to 8 carbon atoms, or phenyl which is optionally monosubstituted or polysubstituted by identical or different substituents, suitable substituents being:

halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl, each of which has 1 to 6 carbon atoms, in imch case straight-chain or branched halogenoalkyl, LeA29088 -5-halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkyl.sulphonyl, each of which has 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, in each case straight-chain or branched alkoxyalkyl, alkoxyalkoxy, alkanoyl, alkoxycarbonyl or alkoximinoalkyl, each of which has 1 to 6 carbon atoms in the individual alkyl moieties, divalent dioxyallcylene having 1 to 5 carbon atoms which is optionally monosubstituied or polysubstituted by identical or different substituents from the series consisting of halogen and/or straight-chain or branched alkyl having 1 to 6 carbon atoms and/or straight-chain or branched halogenoalkyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, or phenyl which is optionally monosubstituted or poly-substituted by identical or different substituents from the series consisting of halogen anid/or straight-chain or branched alkyl having 1 to 6 carbon atoms and/or straight-chain or branched halogenoalkyl having 1 to 6 carbon .15 atoms and 1 to 13 identical or different halogen atonis, R2 represents hydroxyl, cyano, or represents alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, alkyl-carbonyloxy or dialkoxyphosphonyl, each of which has up to 8 carbon atoms in the individual alkyl, alkenyl or alkinyl moieties and each of which is optionally monosubstituted or polysubstituted by identical or different substituents, suitable substituents in each case being:

halogen, strailht-chain. or branched alkoxy having 1 to 8 carbon atoms, or aryl having 6 to 10 car-bon atoms or heteroaryl having 2 to 9 carbon atoms and 1 to 5 hetero atoms - in particular nitrogen, oxygen and/or sulphur -each of these ary1 or heteroaryl substituents optionally being monosubstituted or polysubstituted by identical or different substituents, suitable aryl or heteroaryl substituents being those mentioned in the case of R', LeA29088 -6-RZ furthermore represents amino or aminocarbonyl, each of which is optionally monosubstituted or disubstituted by identical or different substituents, suitable substituents in each case being:

formyl, strailft-chain or branched alkyl having 1 to 8 carbon atoms, straight-chain or branched alkenyl having 2 to 8 carbon atonis, straight-chain or branched alkylsulphonyl having 1 to 8 carbon atoms, carbamoyl, thiocarbamoy.1 or sulphamoyl, each of which is optionally monosubstituted or disubstitutfA by identical or different straight-chain or branched alkyl substituents having 1 to 8 carbon atoni.s, or cycloalkyl, cycloalkylcarbonyl or cycloalkyloxycarbonyl, each of which has 3 to 8 carbon atoms in the cycloalkyl r.noiety, alkylcarbonyl, alkenylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, allcylthio-carbonyl, alkoxy-thiocarbonyl or alkylthio-thiocarbonyl, each of which has 1 to 8 carbon atoms in the individual straight-chain or branched alkyl moieties, in each case - divalent and cyclized alkanediylc:arbonyl or alkanediyloxycarbonyl, each of which has 2 to 6 carbon atoms in the alkanediyl moiety, or arylalkyl, arylalkylcarbcanyl or arylalkyloxycarbonyl, each of which has 6 to 10 carbon atoms in the aryl moiety and 1 to 8 carbon atoms in the straight-chain or branched alkyl moiety and each of which is optionally monosubstituted or polysubstituted in the aryl moiety by identical or different substituents, or aryl, arylcarbonyl or aryloxycarbonyl, each of which has 6 to 10 carbon atoms in the aryl moiety and each of which is optionally monosubstituted or polysubstituted in the aryl moiety by identical or different substituents, suitable aryl substituents in each case being those rr.ientioned in the case of R', R2 furthermore represents aryl, arylcarbonyl, aryloxycarbonyl, arylcarbonyloxy or arylaminocarbonylaminocarbonyloxy, each of which has 6 to 10 carbon atoms in the aryl moiety and each of which is optionally monosubstituted or polysubstiltuted by identical or different substituents, suitable aryl LeA29088 -7-substituents in each case being those mentioned in the case of R', RZ furthermore represents heteroaryl, heteroarylcarbonyl, heteroaryl.oxycarbonyl, heteroarylcarbonyloxy or heteroarylaminocarbonylaminocarbonyloxy, each of which has 2 to 9 carbon atoms and 1 to 5 identical or different hetero atoms - in particular nitrogen, oxygen and/or sulphur - in the heteroaryl moiety and each of which is optionally monosubstituted or polysubstituted by identical or different subst ituents, suitable heteroaryl substituents in each case being the aryl substituents mentioned in the case of R', and R3 represents pecfluoroallcyl or partially fluorinated alkyl having 1 to 25 C
atoms and up to 50 F atoms, X', V, X3 and V iniiependently of orie another in each case represent hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, in each case straight-chain or branched alikyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl, each of which has 1 to 8 carbon atoms, cycloalkyl having 3 to 8 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl, halogenoalkylsulphonyl, each of which has 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, or divalent dioxyalkylene having 1 to 5 carbon atoms which is optionally monosubstituted or polysubstituted by identical or different substituents fi=om the series consisting of halogen and/or straight-chain or branched alkyl having 1 to 4 carbon atoms and/or straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, furthermore represent hydroxycarbonyl, in each case straight-chain or branched alkylcarbonyl or alkoxycarbonyl, each of which has 1 to 6 carbon atoms in the alkyl moiety, cycloalkyloxycarbonyl having 3 to 8 carbon atoms in the cycloalkyl moiety, or amino or aminocarbonyl, each of which is optionally monosubstituted or LeA29088 -8-'2148612 polysubstituted by identical or different substituents, suitable amino substi-tuents in each case being:

in each case straight-chain or branched alkyl having 1 to 6 carbon atoms, halogenoalkyl having I to 6 carbon atoms and 1 to 13 halogen atoms, alkoxyalkyl or alkylcarbonyl, each of which has 1 to 6 carbon atoms in the individual allo/1 moieties, or arylcarbonyl, arylsulphonyl, arylaminocarbonyl or arylmethylsulphonyl, each of which has 6 to 10 carbon atoms in the aryl moiety and each of which is optionally monosubstituted or polysubstituted in the aryl moiety by identical or different substituents, suitable aryl substituents iri each case being those mentioned in the case of R';
furthermore represent aryl, aryloxy, arylthio, arylsulphinyl, arylsulphonyl, arylsulphonyloxy, arylcarbonyl, aryloxycarbonyl, arylthiomethylsulphonyl '15 or arylazo, ea;,h of -which has 6 to 10 cazbon atoms in the aryl 'moiety and each of which is optionally monosubstituted or polysubstituted in the aryl moiety by identical or different substituents, suitable suitable aryl substituents iri each case being those mentioned in the case of R', where at least: one of the substituents X', V, X3 or V represents in each case straight-chain or branched halogenoalkyl (with the exception of the chloromethyl radical'), halogenoalkoxy, halogenoalkylthio, halogeno-allcylsulphinyl, or halogenoalkylsulphonyl, each of which has 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, straight-chain or branched alkylsulphonyl having 1 to 6 carbon atoms or divalent dioxyalkylene having 1 to 5 carbon atoms which is optionally mono-substituted or polysubstituted by identical or different substituents from the series consisting of halogen and/or straight-chain or branched alkyl having 1 to 4 carbon atoms and/or straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, furthermore represents hydroxycarbonyl, in each case straight-chain or LeA29088 -9-branched alkylcarbonyl or alkoxycarbonyl, each of which has 1 to 6 carbon atoms in the alkyl moiety, cycloalkyloxycarbonyl having 3 to 8 carbon atoms in the cycloalkyl moiety, or amino or aminocarbonyl, each of which is optionally monosubstituted or polysubstituted by identical or different substituents, suitable amino substituents in each case being:

in each case slraight-chain or branched alkyl having 1 to 6 carbon atoms, halogenoalkyl having 1 to 6 carbon atoms and 1 to 13 halogen atoms, alkoxyalkyl or alkylcarbonyl, each of which has 1 to 6 carbon atoms in the individual alkyl moieties, or arylcarbonyl, arylsulphonyl, arylaminocarbonyl or arylmethylsulphonyl, each of which has 6 to 10 carbon atoms in the aryl moiety and ea;.h of which is optionally monosubstituted or polysubstituted in the aryl moiety by identical or different substituents, suitable aryl substituents in each case being those mentioned in the case of R';

furthermore represents aryl, arylthio, arylsulphinyl, arylsulphonyl, arylsulphonyloxy, arylcarbonyl, aryloxycarbonyl, arylthiomethylsulphonyl or arylazo, each of which has 6 to 10 carbon atoms in the aryl moiety and each of' which is optionally monosubstituted or polysubstituted in the aryl moiety by identical or different substituents, suitable aryl substituents in each case beir.ig those mentioned in the case of R'.

Particularly prefen-ed compounds of the formula (I) are those in which R' represents hydrogen, in each case straight-chain or branched alkyl or alkoxy, each of which has 1 to 6 carbon atoms, or phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents, suitable substituents being:

halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl, each of which has 1 to 4 carbon LeA29088 - 10-atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl, each of which has 1 to 4 carbon atoms and 1 to 9 identical or diiYerent halogen atoms, in each case straight-chain or branched alkoxyalkyl, a.lkoxyalkoxy, alkanoyl, alkoxycarbonyl or alkoximinoalkyl, each of which has 1 to 4 carbon atoms in the individual alkyl moieties, divalent dioxyalkylene having 1 to 4 carbon atoms which is optionally monosubstituted to hexasubstituted by identical or different substituents from the series consisting of halogen and/or straight-chain or branched alkyl having 1 to 4 carbon atoms and/or straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, or phenyl which is optionally monosubstituted to penta-substituted by identical or different substituents from the series consisting of halogen and/or. straight-chain or branched alkyl having 1 to 4 carbon atoms and/or straight-chain or branched halogenoalkyl having 1-to 4 carbon atoms and 1 to 9 identical or different halogen atoms, RZ represents hydroxyl or cyano, or alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, aTkylthio, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or dialkoxyphosphonyl, each of which has up to 6 carbon atoms in the individual AM, alkenyl or alkinyl moieties and each of which is optionally monosubstituted to pentasubstituted by identical or different halogen substituents, or alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, allcylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or dialkoxy-phosphonyl, each of which has up to 6 carbon atoms in the individual alkyl, alkenyl or alkinyl moieties and each of which is optionally monosub-stituted to trisubstituted by identical or different substituents, suitable substituents in each case being:

straight-chain or branched alkoxy having 1 to 6 carbon atoms, or aryl having 6 or 10 carbon atoms or heteroaryl having 2 to 9 carbon atoms and LeA29088 -11-1 to 4 hetero atoms - in particular nitrogen, oxygen and/or sulphur - each of which is optionally monosubstituted to trisubstituted by identical or dif-ferent substituents, suitable aryl or heteroaryl substituents being those mentioned in ihe case of R', R2 furthermore represents amino or aminocarbonyl, each of which is optionally monosubstitutiA or disubstituted by identical or different substituents, suitable substituents in each case being:

formyl, straight-chain or branched alkyl having 1 to 6 carbon atoms, straight-chain or branched alkenyl having 2 to 6 carbon atoms, straight-chain or branched alkylsulphonyl having 1 to 6 carbon atoms, carbamoyl, thiocarbamoyl or sulphamoyl, each of which is optionally monosubstituted or disubstituted by identical. or different straight-chain or branched alkyl substituents having a to 6 carbon atoms, or cycloalkyl, cycloallcylcarbonyl or cycloalkyloxycarbonyl, each of which has 3 to 7 carbon atoms in the cycloalkyl moiety, alkylcarbonyl, alkenylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio-carbonyl, alkoxy-thiocarbonyl or alkylthio-thiocarbonyl, each of which has 1 to 6 carbon atoms in the individual straight-chain or branched alkyl moieties, in each case divalent and cyclized alkanediylcarbonyl or alkanediyloxycarbonyl, each of which has 2 to 5 cai bon atoms in the alkanediyl moiety, or arylalkyl, arylalkylcarbonyl or arylallcyloxycarbonyl, each of which has 6 or 10 carbon atoms in the aryl moiety and I to 6 carbon atoms in the straight-chain or branched alkyl moiety and each of which is optionally monosubstituted to trisubstituted in the aryl moiety by identical or different substituents, or aryl, arylcarbonyl or aryloxycarbonyl, each of which has 6 or 10 carbon atoms in the aryl moiety and each of which is optionally monosubstituted to trisubstituted in the aryl moiety by identical or different substituents, suitable aryl substituents in each case being those mentioned in the case of R', LeA29088 - 12-R2 furthermore represents aryl, arylcarbonyl, aryloxycarbonyl, arylcarbonyloxy or arylaminocarbonylarninocarbonyloxy, each of which has 6 or 10 carbon atoms in the aryl moiety and each of which is optionally monosubstituted to pentasubstituted by identical or different substituents, suitable aryl substituents in each case being those mentioned in the case of R', RZ furthermore represents heteroaryl, heteroarylcarbonyl, heteroaryloxycarbonyl, heteroarylcarbonyloxy or heteroarylaminocarbonylaminocarbonyloxy, each of which has 2 to 9 carbon atoms and 1 to 4 identical or different hetero atoms - in particular nitrogen, oxygen and/or sulphur - in the heteroaryl moiety and each of which is optionally monosubstituted to pentasubstituted by identical or different substituents, suitable heteroaryl substituents in each case being the aryl substituer-ts mentioned in the case of R', and R3 represent,s CF:;, C',2Fs or C-iF,s, X', V, X3 and V independently of one another in each case represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl, each of which has 1 to 6 carbon atoms, cycloalkyl having 3 to 7 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl, halogenoalkylsulphonyl, each of which has 1 t:o 4 carbon atoms and 1 to 9 identical or different halogen atoms, or divalent dioxyalkylene having 1 to 4 carbon atoms which is optionally monosubstituted to hexasubstituted by identical or different substituents fi-om the series consisting of halogen and/or straight-chain or branched allcyl having 1 to 4 carbon atoms and/or straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, furthermore represent hydroxycarbonyl, in each case straight-chain or branched alkylcarbonyl or alkoxycarbonyl, each of LeA29088 - 13-which has 1 tc- 4 carbon atoms in the alkyl moiety, cycloalkyloxycarbonyl having 3 to 7 carbon atoms in the cycloalkyl moiety, or amino or aminocarbonyl., each of which is optionally monosubstituted or disubstituted by identical or different substituents, suitable amino sub-stituents in each case being:

in each case sitraight-chain or branched alkyl having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 halogen atoms, alkoxyalkyl or alkylcarbonyl, each of which has 1 to 4 carbon atoms in the individual alkyl moieties, or arylcarbonyl, arylsulphonyl, arylaminocarbonyl or arylmethylsulphonyl, each of which has 6 or 10 carbon atom.s in the aryl moiety and each of which is optionally monosubstituted to pentasubstituted in the aryl rrioiety by identical or different substituents, suitable aryl substituents in each case being those mentioned in the case of R'; .
. . : . .
furthermore represent aryl, aryloxy, arylthio, arylsulphinyl, arylsulphonyl, arylsulphonyloxy, arylcarbonyl, aryloxycarbonyl, arylthiomethylsulphonyl or arylazo, each of which has 6 or 10 carbon atoms in the aryl moiety and each of which is optionally monosubstituted to pentasubstituted in the aryl moiety by identical or different substituents, suitable suitable aryl substituents in each case being those mentioned in the case of R';

where at least one of the substituents X', V, X3 or V represents in each case straight-chain or branched halogenoalkyl (with the exception of the chloromethyl radical), halogenoalkoxy, halogenoalkylthio, halogenoalkyl sulphinyl or halogenoalkylsulphonyl, each of which has 1 to 4 carbon atorris and 1 to 9 identical or different halogen atoms, straight-chain or branched alkylsulphonyl having 1 to 4 carbon atoms or divalent dioxyalkylene having 1 to 4 carbon atoms which is optionally monosubsti-tuted to hexasubstituted by identical or different substituents from the series consisting of halogen and/or straight-chain or branched alkyl having 1 to 4 LeA29088 - 14-carbon atoms and/or straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, furthermore represents hyiiroxyc:arbonyl, in each case straight-chain or branched alkylcarbonyl or alkoxycarbonyl, each of which has 1 to 4 carbon atoms in the alkyl moiety, cycloalkyloxycarbonyl having 3 to 7 carbon atoms in the cycloalkyl moiety, or amino or aminocarbonyl, each of which is optionally monosubstitutfxl or disubstituted by identical or different substituents, suitable amino substituents in each case being:

in each case siraight-chain or branched alkyl having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 halogen atoms, alkoxyalkyl or alkylcarbonyl, each of which has 1 to 4 carbon atoms in the individual alkyl moieties, or arylcarbonyl, arylsulphonyl, arylaminocarbonyl or arylmethylsulphonyl, each of which has 6 or 10 carbon atoms in the aryl moiety and each of which is optionally -monosubstiituted to pentasubstituted in the aryl rrioiety by identical or different substituents, suitable aryl substituents in each case being those mentioned in the case of R';
fiuthermore ;represents aryl, arylthio, arylsulphinyl, arylsulphonyl, arylsulphonyloxy, arylcarbonyl, aryloxycaibonyl, arylthiomethylsulphonyl or arylazo, each of which has 6 or 10 carbon atoms in the aryl moiety, such as phenyl or naphthyl, and each of which is optionally monosubstitutEA to pentasubstituted in the aryl moiety by identical or different substituents, suitable suitable aryl substituents in each case being those mentioned in t:he case of R'.

Very particularly pref'erred compounds of the formula (I) are those in which R' represents hycirogen, in each case straiight-chaiin or branched alkyl or alkoxy, each of which has 1 to 4 carbon atoms, or phenyl which is optionally monosubstituted or disubstituted by identical or different LeA29088 - 15-~.1486 12 substituents, suitable substituents being:

halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy, alkylthio, allcylsulphinyl or allcylsulphonyl, each of which has 1 to 3 carbon atoms, in i:ach case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl, each of which has 1 to 3 carbon atoms and 1 to 7 identical or different halogen atoms, in each case straight-chain or branched alkoxyalkyl, alkoxyalkoxy, alkanoyl, alkoxycarbonyl or alkoximinoalkyl, each of which has 1 to 3 carbon atoms in the individual alkyl moieties, divalent dioxyalkylene having 1 to 3 carbon atoms which is optionally monosubstituted to tetrasubstituted by identical or different substituents from the series consisting of halogen and/or straight-chain or branched alkyl having 1 to 3 carbon atoms and/or straight-chain or branched halogenoalkyl having 1 to 3. carbon atoms and 1* to 7 identical or different halogen atoms, or phenyl which is optionally monosubstituted to tri-substituted by identical or different substituents from the series consisting of halogen and/or straight-chain or branched alkyl having 1 to 3 carbon atoms and/or :rtrraight-chain or branched halogenoalkyl having 1 to 3 carbon atoms and 1 to 7 identical or different halogen atoms, Rz represents hyclroxyl or cyano, or alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or dialkoxyphosphonyl, each of which has up to 4 carbon atoms in the individual alkyl, alkenyl or alkinyl moieties and each of which is optionally monosubstituted to trisubstituted by identical or different halogen substituents - in particular fluorine, chlorine and/or bromine substituents -or alkyl, alk:enyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkylcarbonyl,, alkoxycarbonyl, alkylcarbonyloxy or dialkoxyphosphoryl, each of which has up to 4 carbon atoms in the individual alkyl, alkenyl or alkinyl moieties and each of which is optionally monosubstituted or di-LeA29088 - 16-substituted by identical or different substituents, suitable substituents in each case being:

straight-chain or branched alkoxy having 1 to 3 carbon atoms or phenyl which is optionally monosubstituted or disubstituted by identical or different substituents, suitable phenyl substituents being those mentioned in the case of R'.

RZ furthermore represents amino or aminocarbonyl, each of which is optionally monosubstitutcxi or disubstituted by identical or different substituents, suitable substiituents in each case being:

formyl, straight-chain or branched alkyl having 1 to 4 carbon atoms, strai.ght-chain or branched alkenyl haviing 2 to 4 carbon atoms, straiight-chain or branched alkylsulphonyl having *1 to 4 carbon atoms, carbamoyl, thiocarbamoyl or sulphamoyl, each of which is optionally monosubstituted or disubstituted by identical or different straight-chain or branched alkyl substituents having I to 4 carbon atoms, or cycloalkyl, cycloalkylcarbonyl or cycloalkylaxycarbonyl, each of which has 3 to 6 carbon atoms in the cycloalkyl rrioiety, alkylcarbonyl, alkenylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio-carbonyl, alkoxy-thiocarbonyl or alkylthio-thiocarbonyl, each of which has 1 to 4 carbon atoms in the individual straight-chain or branched alkyl moieties, in each case divalent and cyclized alkanediylcarbonyl or alkanediyloxycarbonyl, each of which has 2 to 4 carbon atoms in the alkanediyl moiety, phenylalkyl, phenylalkylcarbonyl or phenylalkyloxycarbonyl, each of which has 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety and each of which is monosubstituted or disubstituted in the phenyl moiety by identical or different substituents, or phenyl, phenylcarbonyl or phenyloxycarbonyl, each of which is optionally monosubstituted or disubstituted in the phenyl moiety by ideiitical or different substituents, suitable phenyl substituents in LeA29088 - 17-each case being those mentioned in the case of R', Rz furthermore represents phenyl, phenylcarbonyl, phenyloxycarbonyl, phenylcarborniloxy oi- phenylaminocarbonylaminocarbonyloxy, each of which is optionally monosubstituted to trisubstituted by identical or different substituents, suitable phenyl substituents in each case being those mentioned in the case of R', R2 furthermore represents heteroaryl, heteroarylcarbonyl, heteroaryl.oxycarbonyl, heteroarylcarbonyloxy, or heteroarylam'vnocarbonylaminocarbonyloxy, each of which has 2 to 9 carbon atoms and 1 tc- 3 identical or different hetero atoms - in particular nitrogen, oxygen and/or sulphur - in the heteroaryl moiety and each of which. is optionally monosubstituted to trisubstituted by identical or different substituents, suitable heter6aryl substituents in each case being the phenyl substiluents mentioned in the case of R'. Heteroaryl radicals which may be mentioned are pyridyl, furanyl, thiophenyl, piperidinyl or pyrrolyl, and R3 represents CF3, X', V, X3 and X4 independently of one another in each case represent hydrogen, chlorine, broinine, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl, each of which has 1 to 4 carbor- atoms, cycloalkyl having 3, 5 or 6 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkyl.thio, halogenoalkylsulphinyl, halogenoalkylsulphonyl, each of which has 1 to 3 carbon atoms and I to 7 identical or different halogen atoms, or divalent dioxyalkylene having 1 to 3 carbon atoms which is optionally monosubstituted to tetrasubstituted by identical or different substituents from the series consisting of halogen and/or straight-chain or LeA29088 - 18-~148 612 branched alkyl having 1 to 3 carbon atoms and/or straight-chain or branched halo;;enoalkyl having 1 to 3 carbon atoms and 1 to 7 identical or different halogen atoms, furthermore represent hydroxycarbonyl, in each case straight-chain or branched alkylcarbonyl or alkoxycarbonyl, each of which has 1 to 3 carbon atoms in the alkyl moiety, cycloalkyloxycarbonyl having 3, 5 or 6 carbon atoms in the cycloalkyl moiety, or amino or aminocarbony:l, each of which is optionally monosubstituted or disubstituted by identical or different substituents, suitable amino sub-stituents in each case being:
in each case straight-chain or branched alkyl having 1 to 3 carbon atoms, halogenoalkyl having 1 to 3 carbon atoms and 1 to 7 halogen atoms, alkoxyalkyl or alkylcarbonyl, each of which has 1 to 3 carbon atoms in the individual alkyl moieties, or phenylcarbonyl, phenylsulphonyl, phenylaminocarbonyl or phenylmethylsulphonyl, each of which 'is optionally monosubstituted to trisubstituted in the phenyl moiety by identical or di:fferent substituents, suitable phenyl substituents in each case being those mentioned in the case of R';

furthermore represent phenyl, phenyloxy, phenylthio, phenylsulphinyl, phenylsulphor.iyl, phenylsulphonyloxy, phenylcarbonyl, phenyloxycarbonyl, phenylthiomethylsulphonyl or phenylazo, each of which is optionally monosubstitutA to trisubstituted in the phenyl moiety by identical or different substituents, suitable suitable phenyl substituents in each case being those mentioned in the case of R', where at least one of the substituents X', V, X3 or V represents in each case straight-chain or branched halogenoalkyl (with the exception of the chloromethyl radical), halogenoalkoxy, halogenoalkylthio, halogenoalkyl,sulphinyl or halogenoalkylsulphonyl, each of which has 1 to 3 carbon atonis and 1 to 7 identical or different halogen atoms, straight-LeA29088 - 19-chain or branched alkylsulphonyl having 1 to 3 carbon atoms or divalent dioxyalkylene having 1 to 3 carbon atoms which is optionally monosubsti-tuted to tetrasiubstituted by identical or different substituents from the series consisting of halogen and/or straight-chain or branched alkyl having 1 to 3 carbon atoms and/or straight-chain or branched halogenoalkyl having 1 to 3 carbon atom.s and 1 to 7 identical or different halogen atoms, furthermore represents hydroxycarbonyl, in each case straight-chain or branched alkylcarbonyl or alkoxycarbonyl, each of which has 1 to 3 carbon atoms in the alkyl moi,-4, cycloalkyloxycarbonyl having 3, 5 or 6 carbon atoms in the cycloalkyl moiety, or amino or aminocarbonyl, each of which is optionally monosubstituted or disubstituted by identical or different substituents, suitable amino substituents in each case being:

in each case :-traight-chain or branched alkyl having 1 to 3 carbon atoms, 1*5 halogenoallcyl. having l to - 3 carbon atoni.s and.1 to *7 halogen atoms, alkoxyalkyl or alkylcarbonyl, each of which has 1 to 3 carbon atoms in the individual alkyl moieties, or phenylcarbonyl, phenylsulphonyl, phenylaminocarbonyl or phenylmethylsulphonyl, each of which is optionally monosubstituted to trisubstituted in the phenyl moiety by identical or different substituents, suitable phenyl substituents being in each case those mentioned in the case of R';

fiuthermore represent phenyl, phenylthio, phenylsulphinyl, phenylsulphonyl, phenylsulphoriyloxy, phenylcarbonyl, phenyloxycarbonyl, phenylthiomethyl-sulphonyl or phenylazo, each of which is optionally monosubstituted to trisubstituted in the phenyl moiety by identical or different substituents, suitable suitable phenyl substituents in each case being those mentioned in the case of R'.

The following substituted benzimidizoles of the general formula (I) may be mentioned individually in addition to the compounds mentioned in the preparation LeA29088 -20-examples:

x z X. N
~
3 ~ / ~}--R3 (~) X N

R
LeA29088 -21-X1 X2 _ X3 X4 Ri R2 Br H CI-CH2-S02- H H i ZHs COOCzHs Br H C6H5-S-CH2-SO2- H H CzHs COOC~Hs H p-CH3-C6H4-S02-0- p-CH3-C6H4-S02-O- H H CzHs COOCzHs Br H C6H5-O-CO- H H CZHS

COOCzIis Br H 0, H H CiHs COOCzHs Br H n-C6H13-0-CO- H H C2H5 COOCzHs Br. H H. H H q.,HS

COOC.~HS
Br H F3C-S- H H C7HS

COOCzHs Ci H F3C-S- H H qHs COO(;Hs Le A 29 088 - 22 -XI X2 X3 X4 R1 . R2 O, ci H CF3 H H qH, O N
COOCHS
0,c/ H F3C-O- H H C~HS
O N
COOCzHs Br H CIFCH-CF2-S- H H CzHs N
/ \COOCzHs Br H CIFCH-CF2-S- H H -O-C2H5 Br H F3C-CHF-CF2-S- H H CzHs N
/ \COOC~HS
Br H F3C-CHF-CF2-S- H H -O-CZHS

N
/ \COOCZHS

COO-n-C3H7 H CF3. ' H H. C.2H~
N
/ \COOCzHs COO-i-C3H7 H CF3 H H C~HS
\COOCzHs COO-n-CqHq H CF3 H H CiH, /N
\COOqHS
L e A 29 088 - 23 -Xi X2 X3 X4 R1 R2 H
COO-s-C4H9 H CF3 H H j'' s ,"- N \COOqHs H
' /
\CooqHs COO-s-C4H9 F3C-0- H H -O-C2H5 COO-n-C3H7 H CF3 H H -O-C2H5 COO-i-C3H7 H CF3 H H -O-C2H5 COO-n-C4Hq H CF3 H H -O-C2H5 COO-s-C4H9 H CF3 H H -O-CZHS

COO-n-C3H7 H F3C-O- H H /N

COO-i-C3H7 H F3C-O- H H
N
~'~OOCzHs H
COO n-C4H9 H' F3C-0- H H s /N
\COpCHs COO-s-C4H9 H F3C-O- H H
/
\coOqHs H
COO-C6H5 H F3C-O- H H j~ s \CooqHs N

COO-n-C3H7 H F3C-0- H H -O-C2H5 C00-i-C3H7 H F3C-0- H H -O-C2H5 COO-n-C4H9 H F3C-O- H H -O-C2H5 LeA2 The 1H-benzimidazoles of the formula (II) mentioned in the preparation of the substituted benzimidazoles of the formula (I) can also be employed as pesticides, just like the compounds of the formula (I).

1H-Benzimidazoles of the formula (II) which are preferably mentioned are those in which the substituents have the preferred and particularly preferred meanings mentioned in the case of the compounds of the formula (I). The following compounds of the formula (II) are mentioned individually:

X

~-C F 3 Xx:) N
N (II) X

x 1 x 2 x 3 x 4 H CF3 Br H
H _C_C\0 H

H -OCF3 Br H

In one aspect, the invention provides a substituted 1H-benzimidazole of the general formula:
XZ
~-CF3 H

wherein X2 to X3 represent the following combinations:
x 2 x 3 CF3 Br -OCF3 Cl -OCF3 Br If, for example, 5(6)-phenyl-2-trifluoromethyl-benzimidazole and chloromethyl ethyl ether are used as starting compounds, the course of the reaction of the process according to the invention can be represented by the following equation:

- 25a -2 CN ~-CF3 + 2 C!-CH2 O-CZHs N
~~--CF3 a-(:'~:N
- HI;i ~

---- +
base N
\>--CF3 N

Formula (II) provide:3 a general definition of the III benzimidazoles required as starting substances for carrying out the process according to the invention.
In this fortnula (II), R3, X', :)(z, X3 and X4 preferably represent those radicals which have already been mentioned in connection with the description of the compounds of the formula (I) accor(iing to the invention as being preferred for these substituents.
The 1H-benzimidazoles of the formula (II) are known or can be obtained in analogy to known processes (cf., for example, J. Amer. Chem. Soc. 71, 1292 [1953]; US 3,576,818).

Formula (III) provides a general defniition of the compounds furkhermore required as starting materials :For carrying out the process according to the invention.

In this formula (III), R' and RZ preferably represent those radicals which have already been mentioned in connection with the description of the substances of the LeA29088 -26-formula (1) according to the invention as being preferred for these substituents.
A preferably represents a leaving radical customary in alkylating agents, preferably halogen, in particular chlorine, bromine or iodine, or in each case optionally substituted allcylsulphonyloxy, alkoxysulphonyloxy or arylsulphonyloxy, such as, in particular, niethariesulphonyloxy, trifluoromethanesulphonyloxy, methoxysulphonyloxy, ethoxysulphonyloxy or p-toluenesulphonyloxy.

A furthermore also represent.s an alcohol, alkanoyloxy or alkoxy group, such as, for example, a hydroxyl, acetoxy or methoxy group.

The compounds of the forrnula (III) are known or can be obtained in analogy to known processes (cf.,, for example, DE 2,040,175; DE 2,119,518; Synthesis 1973, 703).
. . .. . . .
Suitable diluents for canying out the process according to the invention are inert organic solvents. These include, in particular, aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, benzine, benzene, toluene, xylene, cl dorobenz~ene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform or carbon tetrachloride; ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl ether or ethylene glycol diethyl ether; ketones, such as acetone, butanone or methyl isobutyl ketone; nitriles, such as acetonitrile, propionitrile or benzoni-trile; amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide;
esters, such as medryl acetate or ethyl acetate, or bases, such as pyridine, or organic acids, such as formic acid or acetic acid.

The process according to the invention is preferably carried out in the presence of a suitable reaction auxiliary. Suitable reaction auxiliaries are all customary inorganic or organic bases. These include, for exarnple, the hydrides, hydroxides, LeA29088 -27-amides, alcoholates, acetates, carbonates or hydrogencarbonates of alkaline earth metals or alkali met<<ls, such as, for example, sodium hydride, sodium amide, lithium diethylamide, sodium methylate, sodium ethylate, potassium tert.-butylate, sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, c:alcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium hydrogencarbonate, sodium hydrogencarbonate or ammonium carbonate, organolithium compounds, such as n-butyllithium, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, di-isopro-pylethylamine, tetraniethylguanidine, N,N-dimethylaniline, pyridine, piperidine, N-methylpiperidine, N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (I)BN) or diazabicycloundecene (DBU).

In those cases where A in formula (III) represents an alcohol, alkanoyloxy or alkoxy group, other suitable reaction auxiliaries are organic or inorganic acids, ' such as, .for example, suJphurric acid, hydrochloric acid, p-toluenesulphonic acid, perfluorobutanesulphonic acid or strongly acidic ion exchangers.

If appropriate, the process according to the invention can also be carried out in a two-phase system, such as, for example, water/toluene or water/dichloromethane, if appropriate in the presence of a suitable phase-transfer catalyst. Examples of such catalysts which may be mentioned are: tetrabutylammonium iodide, tetrabutylammonium bromide, tetrabutylammonium chloride, tributyl-methyl-phosphonium bromicle, trimethyl-C13/C15-alkylammonium chloride, trimethyl-C13/C15-alkylammonium bromide, dibenzyl-dimethyl-ammonium methylsulphate, dimethyl-C12/C.14alkylbenzylammonium chloride, dimethyl-C12/C14-alkyl-benzyl-ammonium bromide, tetrabutyl ammonium hydroxide, triethylbenzylammonium chloride, methyltrioctylammonium chloride, trimethylbenzylammonium chloride, 15-crown-5, 18-crown-6 or tris-[2-(2-methoxyethoxy)-ethyl]-amine.

When canying out the process according to the invention, the reaction temperatures can be varied within a substantial range. In general, the process is LeA29088 -28-carried out at temperatures between -70 C and +200 C, preferably at temperatures between 0 C and 130 C.

The process according to the invention is conventionally carried out unde:r atmospheric pressure. However, it can also be carried out under increased or reduced pressure.

To carry out the proa~ss according to the invention, 1.0 to 5.0 mol, preferably 1.0 to 2.5 mol, of compoi.znd of' the formula (III) and, if appropriate, 0.01 to 5.0 mol, preferably 1.0 to 3.0 rnol, of reaction auxiliary are generrally employed per mole of 1 H-benzimidazole of the formula (H).

In a particular embodiment, it is also possible to first silylate the 1H-benzimidazoles of the formula (II) in a preceding reaction step with the aid of conventional silylatic-n processes, for example -using hexamethyldisilazane or trimethylsilyl chloride, if appropriate in the presence of a suitable catalyst, such as, for example, sulphuric acid, trifluoroacetic acid, ammonium sulphate, imidazole or saccharin, at temperatures between -20 C and +50 C, and to react the 1-trimethyl-silylbenzimidazoles thus obtainable in a subsequent second step with alkylating agents of the formula (II) using the process according to the invention. In this case, it is advantageous to add tin tetrachloride to the alkylation reaction to act as a catalyst (cf., for emunple, Chem. Heterocycl. Comp. USSR 24, 514 [1988]) The reaction is carried out and the reaction product is worked up and isolated by known processes (cf in this context also the preparation examples).

The end products of the fonnula (I) are purified with the aid of conventional processes, for example by column chromatography or by recrystallization.

They are characterized with the aid of the melting point or, in the case of compounds which da not form crystals -in particular in the case of regioisomer LeA29088 -29-~1.4 3 6 12 mixtures -, with the ziid of proton nuclear resonance spectroscopy ('H-NMR).
The active compounds are suitable for combating animal pests, preferably arthropods and nematodes, in particular insects and arachnids encountered in agriculture, in forests, in the protection of stored products and materials, and in the hygiene sector. They are active against normally sensitive and resistant species and against all or some stages of development.

The abovementioned pests include:
From the order of the Isopoda, for example, Oniscus asellus, Armadillidium vulgare and Porcellio scaber;
from the order of the Diplopoda, for example, Blaniulus guttulatus;
from the order of ihe Chilopoda, for example, Geophilus carpophagus and Scutigera spec;
from the order of the Symphyla, for example, Scutigerella immaculata;
from the order of the Thysanura, for example, Lepisma saccharina;
from the order of the Collembola, for example, Onychiurus armatus;
from the order of the Orthoptera, for example, Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis and Schistocerca gregaria;
from the order of the Dermaptera, for example, Forficula auricularia;
from the order of the Isoptera, for example, Reticulitermes spp.;
from the order of the Anoplura, for example, Phylloxera vastatrix, Pemphigus spp., Pediculus humanus corporis, l:-laematopinus spp. and Linognathus spp.;
from the order of the Mallophaga, for example, Trichodectes spp. and Damalinea spp=;
from the order of the Thysanoptera, for example, Hercinothrips femoralis and Thrips tabaci;
from the order of the Heteroptera, for example, Eurigaster spp., Dysdercus LeA29088 -30-intermedius, Piesma (juadrata, Cimex lectularius, Rhodnius prolixus and Triatoma spp.;
from the order of the Homoptera, for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigenun, Hyalopterus muidinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, L.ecaiium comi, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. and Psylla spp.;
from the order of the Lepidoptera, for example, Pectinophora gossypiella, Bupalus piniarius, Chei.matobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Laphygrna exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni; Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofinannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fiuniferana, Clysia ambiguella, Homona magnani:ma and Torlrix viridana;
from the order of the Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Bruchidiu> obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Ani:hrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conodenas spp., Melolontha melolontha, Amphimallon solstitialis and Costelytra zealandica;
from the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp.;

LeA29088 -31 -from the order of the: Diptera, for example, Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypode:rma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae and Tipula paludosa;
from the order of the Siphonaptera, for example, Xenopsylla cheopis.
Ceratophyllus spp.;
from the order of the Arachnida, for example, Scorpio maurus and Latrodectus mactans;
from the order of the .Acarina, for example, Acanas siro, Argas spp., Omithodoros spp., Deimanyssus gallinae, Eriophyes ribis, Phyllocoptnrta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Choirioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia 15. ~ praetiosa, Panonychus 'spp. and Tetranychus. spp.

The plant-parasitic nematodes include Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, 'Tylenchulus semipenetrans, Heterodera spp., Meloidogyne spp., Aphelenchoides spp., Longidonts spp., Xiphinema spp., Trichodorus spp..
:20 The active compound:, according to the invention are not only active against plant, hygiene and stored product pests, but also, in the veterinary medicine sector, against animal parasites (ectoparasites and endoparasites) such as scaly ticks, Argasidae, scab mites, Trombidae, flies (stinging and sucking), parasitic fly larvae, :25 lice, hair lice, bird lio.-, fleas and endoparasitic worms.

They are active against norrnally-sensitive and resistant species and strains and against all parasitic and non-parasitic development stages of the ecto- and endoparasites.
:30 The active compounds according to the invention are distinguished by a powe:rful LeA29088 -32-insecticidal activity.

They can be emplo;yed particularly successfully for combating plant-injurious insects, such as, for example, against the larvae of the mustard beetle (Phaedon cochleariae) or against the caterpillars of the cabbage moth (Plutella maculipennis) or against other Plutella species, such as, for example, Plutella xylostella, or against the tobacco bud worm (Heliothis virescens) and for combating plant-injurious mites, suchi as, f'or example, against the greenhouse red spider mite (Tetranychus urticae), or for combating plant-injurious nematodes, such as, for example, against the nematode species Globodera rostochiensis.

In addition, the active compounds according to the invention can also be employed for combating hygiene and stored product pests, such as, for example, against the house fly (Musca donnestica) or against the grain weevil (Sitophilus granarius) or against cockrokh'species, such as, for example, Blattella germanica or Periplaneta americana.

Moreover, the active compounds according to the invention can be employed particularly successfully for combating parasitic pests of warm-blooded species, :20 such as, for example, against scab mites (Psoroptes ovis).

In addition, the active compounds according to the invention also have a powerful fungicidal activity and can be employed in practice for combating undesired microorganisms. The active compounds are also suitable for use as fungicides.
Fungicidal agents in plant protection are employed for combating Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiornycetes and Deuteromycetes.

Some causative organi-sms of fungal diseases which come under the generic names listed above may be mentioned as examples, but not by way of limitation:
LeA29088 -33-~1486 12 Pythium species, such as, for example, Pythium ultimum;
Phytophthora species, such as, for exarnple, Phytophthora infestans;
Pseudoperonospora species, such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubense;
Plasmopara species, such as, fbr example, Plasmopara viticola;
Peronospora species, such as, for example, Peronospora pisi or Peronospora brassicae;
Erysiphe species, such as, for example, Erysiphe graminis;
Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;
Podosphaera species, such as, for example, Podosphaera leucotricha;
Venturia species, sucht as, for example, Venturia inaequalis;
Pyrenophora species, such as, for example, Pyrenophora teres or Pyrenophora graminea (conidia fonn: Drechslera, synonym: Helminthosporium); .
15Cochliobolus species, such as,' for example, Cochliobolus sativus (conidia forin:
Drechslera, synonym: Helminthosporium);
Uromyces species, such as, for example, Uromyces appendiculatus;
Puccinia species, such as, for example, Puccinia recondita;
Tilletia species, such as, for example, Tilletia caries;
Ustilago species, such as, for example, Ustilago nuda or Ustilago avenae;
Pellicularia species, such as, for example, Pellicularia sasakii;
Pyricularia species, such as, for example, Pyricularia oryzae;
Fusarium species, such as, for example, Fusarium culmotwn;
Botrytis species, such as, for example, Botrytis cinerea;
Septoria species, such as, for example, Septoria nodorum;
Leptosphaeria species, such as, for example, I.eptosphaeria nodorum;
Cercospora species, suich as, for example, Cercospora canescens;
Altemaria species, such as, for example, Altemaria brassicae and Pseudocercosporella species, such as, for example, Pseudocercosporella herpotrichoides.

Le A 29 088 - 34 -'2148 612 The good toleration, by plants, of the active compounds, at the concentrations required for combating plant diseases, perniits treatment of above-ground parts of plants, of vegetative propagation stock and seeds, and of the soil.

In this context, the acitive compounds according to the invention can be employed with particular success for conibating cereal diseases such as, for example, against the causative organisrn of powdety mildew of cereals (Erysiphe graminis) or for combating diseases in fruit and vegetable growing such as, for example, against the causative organism of tomato blight (Phytophthora infestans) or against the causative organism oi' downy mildew of grapevine (Plasmopara viticola), or for combating rice diseases such as, for example, against the causative organism of rice blast disease (Pyricularia oryzae).

Moreover, if used at appropriate application rates, the active compounds according to the invention can bE; used as defoliants, desiccants, agents for destroying broad-leaved plants and, especially, as weed-killers. By weeds, in the broadest sense, there are to be understood all plants which grow in locations where they are undesired. Whether tl7e substances according to the invention act as total or selective herbicides depends essentially on the amount used.
The active compound3 according to the invention can be used, for example, in connection with the fcdlowing plants:

DigUledon weeds of ~:hegenera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindemia, L.amium, Veronica, Abutilon, Emex, Datwa, Viola, Galeopsis, Papaver and Centaurea.

I?icotvledon cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, lpomoea, Vicia, Nicotiana, Lycopersicon, Arachis, LeA29088 -35-Brassica, Lactuca, Cucumis and Cucurbita.

Monocotvledon weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cypeivs, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecunas and Apera.

onoco edon cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Sacchatvni, Ananas, Asparagus and Allium.
However, the use of the active compounds according to the invention is in no way restricted to these genera, but also extends in the same manner to other plants.

The compounds are suitable, depending on the concentration, for the total combating of weeds, for example on industrial tenain and rail tracks, and on paths and squares with or without tree plantings. Equally, the compounds can be employed for combating weeds in perennial cultures, for example afforestations, decorative tree plantinigs, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hopfields, and for the selective combating of weeds in annual cultures.

The active compounds according to the invention can be employed with particular :25 success here for combating monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon cultures, such as, for example, maize, wheat or soya.

Depending on their particular physical andlor chemical properties, the active compounds can be converted into the customary formulations, such as solutions, emulsions, suspensioris, powders, foams, pastes, granules, aerosols, natural and LeA29088 -36-synthetic materials iinpregnated with active compound, very fine capsules in polymeric substance;; and in coating compositions for seed, furthermore in formulations used with buniing equipment, such as fi.unigating cartridges, fumigating cans and futnigating coils and the like, as well as ULV cold- and warm-mist formulaticins.

These formulations are produced in a known maruier, for example by mixing the active compounds with extenders, that is liquid solvents, liquefied gases under pressure and/or solid carriers, optionally with the use of surface-active agents, that is emulsifying agents and/or dispersing agents and/or foam fonming agents. In the case of the use of water as an extender, organic solvents can, for example, also be used as auxiliary solvents. As liquid solvents, there are suitable in the main:
aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylene,s or methylene chloride,.aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum firactions, alcohols, such as butanol or glycol as well as their ethers and esters, ket:ones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexan.one, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, as well as water; by liquefied gaseous extenders or carriers there are meant liquids which are gaseous at normal temperature and under atmos-pheric pressure, for example aerosol propellants, such as halogenohydrocarbons as well as butane, propane, nitrogen and carbon dioxide; as solid carriers there are suitable: for example ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, nlontmorillonite or diatomaceous earth, and ground synthetic minerals, such as higNy disperse silica, alumina and silicates; as solid carriers for granules there are suitable, for example crushed and fra.ctionated natural rocks such as calcite, marble, ptnnice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; as emulsifying and/or foam-forming agents there are suitable: for example non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example LeA29088 -37-_ 2~.48 6 12 alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates as well as albumen hydrolysis products; as dispersing agents there are suitable:
for example lignin-sulphite waste liquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latexes, such as gum arabic, polyvinyl alcohol and polyvinyl acetate;, as well as natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations.
Further additives can be mineral and vegetable oils.
It is possible to use caAorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and melml phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and tin.

The formulations in general contain between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.

The active compowlds according to the invention can be present in their commercially available formulations and the use forms prepared with these formulations as a rr.iixture with other active compounds, such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth-regulating substances or herbicides. The insecticides include, for example, phosphates, carbamates, carboxyl ates; chlorinated hydrocarbons, phenylureas and substances produced by microorganisms, inter alia.

The active compounds according to the invention can furthermore be present in their commercially available formulations and in the use forms, prepared from these formulations, as a mixture with synergistic agents. Synergistic agents are compounds which ir.icrease the action of the active compounds, without it being necessary for the syriergistic agent added to be active itself.

LeA29088 -38-j14 36 12 The active compound content of the use forms prepared from the commercially available formulations can vary within wide limits. The active compound concentration of the use forms can be from 0.0000001 to 95 per cent by weight of active compound, preferably between 0.0001 and 1 per cent by weight.
The compounds are employed in a customary manner appropriate for the use forms.

When used against hygiene pests and pests of stored products, the active compounds are distinguished by an excellent residual action on wood and clay as well as a good stability to alkali on limed substrates.

The active compourids which can be used according to the invention are also suitable for combatir-g insects, mites, ticks etc. in the sector of animal keeping and cattle breeding, betteT results, for example. higher milk production, greater weight, more attractive animal pelt, longer life etc., can be achieved by combating the pests.

The application of the active compounds which can be used according to the invention occurs in this sector in a known fashion, for example, by oral application in the form of, tablets, capsules, potions or granules, by means of dermal or external application in the form of, for example, dipping, spraying, pouring-on, spotting-on and dusting, as well as by means of parenteral application in the form of, for example, inje;.tion, and, furthermore, by means of the feed-through process.
In addition, application as moulded articles (collar, ear tag) is also possible.

When used as fungicides, the active compounds according to the invention can also be present in the formulations as a mixture with other known active compounds, such as fungicides, insecticides, acaricides and herbicides, and in mixtures with fertilizers and growth regulators.

LeA29088 -39-21~3 16 12 When used as fungicides, the active compounds can be used as such, in the form of their formulations, or the use forms prepared therefrom, such as ready-to-use solutions, suspension,, wettable powders, pastes, soluble powders, dusts and granules. They are used in the customary manner, for example by watering, spraying, atomizing, scattering, dusting, foaming, brushing on and the like.
It is furthermore possible to apply the active compounds by the ultra-low volume method or to inject the active compound formulation or the active compound itself into the soil. The seeci of the plants can also be treated.

When used as fungicides in the treatment of parts of plants, the active compound concentrations in the use forms can be varied within a substantial range. They are, in general, between 1 and 0.0001% by weight, preferably between 0.5 and 0.001%
by weight.

When used as fungicides in the treatment of seed, amounts of active corrqwund of 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g, are generally required.
When used as fungicides in the treatment of soil, active compound concentrations of 0.00001 to 0.1% by weight, preferably 0.0001 to 0.02% by weight, are required at the place of action.

When used as herbiciiies, the active compounds according to the invention, as such or in the form of their fonnulations, can also be used as a mixture with known herbicides for combating weeds, fuiished formulations or tank mixes being possible. Suitable herbicides for the mixtures are known herbicides, for example anilides such as, for example, diflufenican and propanil; arylcarboxylic acids such as, for example, dichloropicolinic acid, dicamba or picloram; aryloxyalkanoic acids such as, for examplo-1, 2,4-D, 2,4-DB, 2,4-DP, fluroxypyr, MCPA, MCPP and triclopyr; aryloxy-phenoxy-alkanoic esters such as, for example, diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl;
azinones such as, for example, chloridazon and norflurazon; carbamates such as, for LeA29088 -40-example, chlorpropham, desmedipham, phenmedipham and propham; chloro-acetanilides such as, for example, alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilacliilor and propachlor; dinitroanilines such as, for example, oryzalin, pendimethalin and trifluralin; diphenyl ethers such as, for example, acifluorfen, bifenox, fluoroglycofen, fomesafen, halosafen, lactofen and oxyfluorfen; ureas such as, for example, chlortoluron, diuron, fluometuron, isoproturon, linuron and methabenzthiazuron; hydroxylamines such as, for example, alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim;
imidazolinones such as, for example, imazethapyr, imazamethabenz, imazapyr and imazaquin; nitriles such as, for example, bromoxynil, dichlobenil and ioxynil;
oxyacetamides such as, for example, mefenacet; sulphonylureas such as, for example, amidosulfiiron, 'bensulfiuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, metsu].furon-methyl, nicosulfiaron, primisulfuron, pyrazosulfuron-ethyl, thifensulfuron-methyl, triasulfuron and tribenuron-methyl;
thiocarbamates such as, for example, butylate, cycloate, di-allate, EPTC,- esprocarb, molinate, prosulfocarb, thiobeiicarb and tri-allate; triazines such as, for example, atrazine, cyanazine, simazine, simetxyn, terbutryn and terbutylazine; triazinones such as, for example, hexazinone, metaniitron and metribuzin; others such as, for example aminotriazole, benfuresate, bentazone, cinmethylin, clomazone, clopyralid, difenzoquat, dithiopyr, ethofiunesate, fluorochloridone, glufosinate, glyphosate, isoxaben, pyridate, quinchlorac, quinmerac, sulphosate and tridiphane.

When used as herbicides, a mixture with other known active compounds, such as fungicides, insecticicles, acaricides, nematocides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.

The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by watering, spraying, atomizing or scattering.
LeA29088 -41 -When used as herbicides, the active compounds according to the invention can be applied either before or after emergence of the plants. They can also be incorporated into the soil before sowing.

When used as herbicides, the amount of active compound used can vary within a substantial range. It depends essentially on the nature of the desired effect. In general, the amounts used are between 0.001 and 10 kg of active compound per hectare of soil surface, preferably between 0.005 and 5 kg per hectare.

Accordingly, the invention also provides:
compositions comprising the compounds of the invention;
methods of preparing the compositions and methods of combating pests and parasites using the compounds and compositions of the invention; and uses of the compounds and compositions of the invention for combating pests and parasites.

The preparation and use of the active compounds according to the invention can be seen from the following Examples.

PiepFUation Exama:

~

~
--N
~--CF3 ~ N
~
' N I \C F3 CHZ O-CZHs "~ N

7.9 g (0.03 mol) of 5(6)-phenyl-2-trifluoromethyl-lH-benzimidazole and 8.2 g (0.06 mol) of pulveri:,-,ed potassium carbonate are refluxed for 15 minutes in 70 ml of ethyl acetate, and the mixture is subsequently treated with 3.9 g (0.04 mol) of (chloromethyt ethyl ether in :20 ml of ethyl acetate and refluxed for a further 4 hours, with stirring. For working up, the cooled reaction mixture is washed twice using in each case 40 ml of water, dried over sodium sulphate, and concentrated in vacuo, and the m;idue is purified by chromatography over silica gel (eluent:
dichloromethane).
6.9 g (71% of iheory;) of 1-ethoxymethyl-5(6}phenyl-2-trifluoromethyl-benzimidazole are obtained as a regioisomer mixture in a ratio of 1:1.

'H-NMR (DMSadb/tetramethylsilane): d = 5.84 (s, 2H); 5.89 (s, 2H) ppm [in each case N-CH -U-].

The following substituted benzimidazoles of the general formula (I) are obtained in a corresponding nianner and following the general preparation instructions:
LeA29088 -43-x N
\ ~ \ ~~-CF3 {I) X3~ ~ N

X CH-R
II
R
Ex. Xl :(2 X3 X4 Rl R2 Physical No. Properties 2 Br H CF3 H H CH M.P. 90-90 C
-N

//

3 Br H CF3 H H -N,qHs m.p.70-74 C
C-OCHI
//

4 Br H CF3 H H ,n-qH7 m.p.75-79 C
-N

//

Br H CF3 H H -CH=CH2 m.p.53-56 C
(H) (CF3) (H) (Br) (82:18) 6 Br H CF3 H H -CO-C(CH3)3 m.p.120-123 C
7 Br H CF3 H H -CH2-C6H5 m.p.80-84 C
8 Br H CF3 H H -CO-C6H5 m.p.163-166 C

LeA29088 -44-~148612 Ex. X' XZ X3 X4 Rl R2 Physical No. Properties 9 Br H( CF3 H H -CH=CH-CH3 m.p.80-83 C
(H) (CF'3) (H) (Br) (93:7) Br F.[ CF3 H H C1 m.p.60-63 C
v,,CH =C
C H (E/Z=64:36) 11 H (CH3)=,N-CO- H H H -O-C2H5 1 H-NIvR*):
(13) ((CH3)2N-CO-) 5.59; 5.60;
7.54-8.62 (1i) (F2CH-CF2-O-) 13 Br H CF3 H H -O-i-C3H7 1H-NMR
(H) (CF'3) (H) (Br) 5.94; 6.00 (63:37) 14 Br H: CF3 H H -O-n-C3H7 M.P. 70 73 C
(H) (CF'3) (1D (Br) (76:24) Br H: CF3 H H -0-(CH2)3-C6H5 1H-NMR*):
(H) (CF'3) . ~) (Br) 5.94; 6.00.
(64:36) 16 Br H: CF3 H H-O-CH2-C=-CH m.p.71-73 C
17 Br H: CF3 H H m.p.195-200 C
0 _ -O-C-NH-c-NH ~ , C!

18 Br H: CF3 H H-O-CO-C(CH3)3 m.p.98-101 C
19 Br H CF3 H H C 1H-NMR#):
(H) (CF 3) (H) (Br) -O-CH2 0 6.08; .14 (70:30) LeA29088 -45-Ex. xl X2 X3 X4 Rl R2 Physical No. Properties 20 Br H CF3 H H -O-C2H5 m.p.82-85 C
(H) (CF3) (H) (Br) (87:13) 21 Br H CF3 H H CH a m.p.128-130 C
-N
C-OCsHs //

22 Br H CF3 H H CN m.p.147-151 C
23 H C6B5-CO- H H H -O-C2H5 1H-NMR*):
(H) (C6H5-CO-) 5.89 (1:1) 24 H C6H5-CO- H H H _N ci~ m,p,105-109 C
(Ei) (C6H5-CO-) ~C-ocH, (1:1) o 25 H C6H5-CO- H H H CN m,p.102-105 C
Ci) (C6H5-CO-) (1:1) 26 H Ce~115.' H H If -N H_NMR*).
0-1) (C6H5) 'C-OCH66,02; 5,98 o/ (40:60) 27 Br H CF3 H H -0-CH2-CH2-O- cH3 1H-1VMRR):
(H) (C1'3) (H) (Br) 5.94; 6.03 28 Br H CF3 H H -N qHs m.p.103-106 C
C-0CzHs //

LeA29088 -46-~14 8 6 12 Ex. X1 ;K2 X3 X4 R1 R2 Physical No. Properties 29 Br H CF3 H H in"CH, m.p.92-94 C
-N

//

30 Br l~ CF3 H H / icA m.p.70-73 C
-N
C-OC=HS
//

31 Br H CF3 H H /CH2 'CHs nyp.70-74 C
-N
// C-OCzHs 32 Br F[ CF3 H H /rHs m.p.70-73 C
-N
.=
C-03C,H9 .

33 H -()-(CH2)3-0- H H -O-C2H5 m.p.70-74 C
34 Br H CF3 H H -N(CH3)2 (x HCI) 35 H -()-(CH2)3-0- H H -N CH3 m.p.105-108 C

//

LeA29088 -47-'z14861?
Ex X1 X2 X3 X4 R1 R2 No. Physical Properties 36 Br H CF3 H H /CC~Hii m.p.80-83 C
-N

/

37 Br H CF3 H H c6Hs m.p,135-136 C
-N
C-OCiHs S

38 Br 1I CF3 H H CH2 CH=CH, m.p.76-78 C
C-OC=HS

39 Br H CF3 H H ~aHs m.p,174-176 C
-N
// C--OC2Hs S

40 Br H CF3 H H ,CH2 CH CHj -N
C-OCm.p.109-112 C
iHs //

41 Br CF3 H H -S-CH3 m.p.56-60 C
(H) (CF'3) (H) (Br) (1:1) (CI) (CF3) LeA29088 -48-Ex. X1 =(2 X3 X4 RI R2 No. Physical Properties 43 H CF3 Cl H H ci /-\
44 H C1 CF3 H H cl /-\
45 H CF3 Cl H H Cl ~ D C
46 H (:l CF3 H H Cl \-/ C
47 H CF3 Ct H H
((;1) (CF3) &HO=
48 H ClF3 Cl H H O

(C:1) (CF3) -P-OC=HS
OqHS
49 H CF3 Cl H H Cg3 (C:l) (CF3) \-/

50 H CF3 CI H -O-C2H5 -O-C2H5 Ii1.p.90-92 C
(C1) (CF3) 51 H CF3 Cl H H -CO-C(CH3)3 (Cl) (CF3) (CI) (CF3) LeA29088 -49-Ex. X1 X2 X3 X4 R1 R2 Physical No. Properties 55 H CF3 Cl H H -CO-C6H5 (Cl) (CF3) 56 H CF3 Cl H H -OCH(CH3)2 1H-NMR
(CI) (CF3) A: 5.66; 7.83;
8.23 B: 5.71; 8.00;
8.06 57 H CF3 Cl H H 0 _ 1H-NMIIt*):
(1~1) (CF3) -C ~ i F A: 5.67; 7.43;
8.33 ' B: 5.73; 7.63;
8.10 58 H CF3 Cl H H O _ 1H-NMR*):
(CI) (CF3) -C ~ i CaHs A: 5.75; 7.45;
8.30 B : 5.78; 7.75;
7:97 59 -H CF3 CI H H p Cxs 1H-NMe):
(C1) (CF3) C A: 5.60; 7.41;
CH 8.28 ' B: 5.63; 7.63;
8.06 60 H CF'3 Cl H H O _ 1H-NNIIt:
(Cl) (CF3) -C ~ i C A: 5.71; 7.42;
Cl 8.28 B: 5.75; 7.66;
8.06 IeA29088 -50-Ex. Xi )'2 X3 X4 Rl R2 Physical No. Properties 61 H CF3 CI H H 0 C 1H_NMR*):
((;1) (CF3) -C 0 A: 5.67; 7.39;
C 8.29 B: 5.73, 7.60 and 8.05 62 H CF3 CI H H 0 _ 1H-NMR*):
(Cl) (CF3) -C ~ i B A: 5.83; 7.68;
8.25 B: 5.90; 7.75;
8.03 63 H CF3 CI H H O _ 1H-NMR*):
(CI) (CF3) -C ~ / C A: 5.60; 7.38;
H3C 8.26 B: 5.64, 7.62 and 8.04 64 H CF3 Cl H H 0 Cl C 1H-NMR*):
(CI) (CF3) 5.30;'7.54;
8:22 B: 5.35; 7.75;.
8.02 65 H CF:; C1 H H 0 Cl 1H-NMR*):
(Cl) (CF3) -CCH2 ~:_\ C A 5.11; 7.15;
8.23 B: 5.15; 7.40;
8.02 IeA29088 -51 -2148f12 Ex. Xi X2, X3 X4 RI R2 Physical No. Properties 66 H CF 3 Cl H CH3 CN 1H-NMR}):
(Cl) (CF3) A: 5.60; 7.80;
8.34 B: 5.65; 7.96;
8.13 s 67 H CF3 Cl H H ,~Hs IH-NMR :
(C!) (CF3) -N
C-OCHA: 5.86; 7.98;

8.33 0 B: 5.90; 8.03;
8.21 68 H CF3 Cl H H ,~~H9 1H-N1~IIt}):
(CI) (CF3) -N A 5.85; 7.99;
/C-0C1H5 8.32 0 B: 5.90; 8.02;
8.22 69 H CF3 Cl H H CH 3 1H-NMR*):
(Cl.)(CF3) -N A:5.87;'7.98;

i~ 8.34 0 B: 5.91; 8.05;
8.22 70 H -C,-CF2-CF2-O- H H -O-CH(CH3)2 1H-NMR*):
5.61; 7.45; 7.65 71 H -Cl-CF2-CF2-O- H H -CO-C6H5 m.p.141-143 C
72 H -G-CF2-CF2-0- H H CN mp.132-134 C
73 H -O-CF2-O- H H -0-CH(CH3)2 m.p.76-78 C
LeA29088 -52-~148 612 Ex.
No. Xl ,i{2 X3 X4 Rl R2 Physical Properties 74 H -O-CF2-O- H H -CO-C6H5 m.p,188-189 C
75 H -O-CF2-O- H H CN mp,145-147 C
76 H CF3 Br H H -O-CH(CH3)2 1H_NMR'):
(13r) (CF3) A: 5.65; 8.03;
8.23 B: 5.69; 8.05;
8.20 77 H CF3 Br H H Cl lH-N1VR.):
(Br) (CF3) ~~C A: 5.56; 7.59;
8.29 B: 5.59; 7.61;
8.26 78 H CF3 H H H -O-C2H5 1H-NMF:*):
(Fi) (CF3) A: 5.38; 7.18-7.94;.
B: 5.40 79 H CF3 H H H OH 1H-N1vIR
(F~) (CF3) 2.2; 7.76;
8.1 80 H CF'3 Br H H -O-C2H5 IH-NMP, ).
(B(CF3) A: 5.64; 8.03;
8.21 B: 5.72; 8.06;
8.18 81 H CF3 Br H H -O-C2H5 mp.66 C
82 H Br CF3 H H -O-C2H5 1H-NMR*):
B: 5.72; 8.05;
8.17 Le A 29 088 - 53 -214Sl 6 12 Ex. X1 X2 X3 X4 Rl R2 Physical No. Properties 83 H CF3 Br H H -O-n-C3H7 1H-NMR*):
(Br) (CF3) A: 6.67; 8.08;
8.27 B: 5.69; 8.11;
8.25 84 H CF3 Br H H-O-CH2-C=-CH 1H-NM.R*):
(l3r) (CF3) A: 5.51; 7.89;
8.17 B: 5.71; 7.93;
8.21 85 H CF3 Cl H H -O-C2H5 1H-NMR*):
(Cl) (CF3) A: 5.69; 7.82;
8.23 B: 5.71; 8.00;
8.03 86 H C.F3 CI H H -O-C2H5 mp.73 C
87 H (11 CF3 H H -O-C2H5 1H-NMR*):
B: 5.71; 8.00;
8.03 88 H C]?3 Cl H H-O-CH(CH2F)2 1H-NMR*):
(C:1) (CF3) A: 5.83; 7.78;
8.03 B: 5.89; 8.01;
8.26 89 H CF3 Cl H H -O-n-C3H7 1H-NMR*):
(Cl) (CF3) . A: 5.70; 7.80;
8.06 B: 5.73; 7.99;
8.21 LeA29088 -54-Ex. X1 X2 X3 X4 Rl R2 Physical No. Properues 90 H CF3 Cl H H-O-CH2-C. CH 1H-NMR*):
;CI) (CF3) A: 5.73; 7.81;
8.04 B : 5.77; 8.00;
8.02 91 H (:F3 Cl H H CH3 1H-NMR*):
(Cl) (CF3) !NN A: 5.90; 8.00;
C-OC=HS
i/ 8.21 0 B: 5.93; 8.03;
8.31 =
92 H CF3 Cl H H ,C2Hs 1H-NMR*):
(Cl) (CF3) ~N A: 5.89; 8.00;
C-OC2Hs 8.21 0 B: 5.95; 8.03;
8.33 93 H CF3 Cl H H. /n-qH7 1H-NMTt*):
(C1) (CF3) = -N A: 5.89; 8:00;
C-OrHs i/ 8.22 0 B: 5.91; 8.04;
8.32 94 H CF3 Cl H H -CO-OC2H5 mp.73 C
((:1) (CF3) 95 H CF3 Cl H CH3 -CO-OC2H5 1H-NMR*):
((:1) (CF3) A: 1.91; 5.34;
7.57; 8.12 96 H -O-CF2-O- H H -O-C2H5 m.p.92 C
LeA29088 -55-Ex. X1 X2 X3 X4 Rl R2 Physical No. Properties 97 H -O-CF2-O- H H-O-CH(CH2F)2 mp,.64 C
98 H -O-C:F2-O- H H -O-n-C3H7 m.p, 41 C
99 H -O-CF2-O- H H-O-CH2-C CH mp.87 C
100 H -O-CF2-O- H H -N CI43 mp.93 C
C-OCZHS
//

101 H -O-CF2-O- H H -N ,C7HS mp.67 C
C-OCzHs //

102 H -O-CF2-O- H H /rl-qH., 1H-NIvIIZ*~-____N 5.89; 7.51 C-OC=HS
//

103 H -,O-CF2-CF2-O- H H -O-C2H5 1H-NIvSR*):
5.63; 7.52; 7.63 104 H -1:)-CF2-CF2-O- H H -0-CH(CH2F)2 1H-NMR*):
5.82; 7.42; 7.68 105 H -O-CF2-CF2-O- H H ,~3 m.p.118 C
-N

//

LeA29088 -56-Eh. X1 X2 X3 X4 Rl R2 Physical No. Properties 106 H -O-CF2-CF2-O- H H SHs m.p.85 C
-N
C-OCZH
//

107 H -O-CF2-CF2-O- H H / n-CsHT n1.p.103 C
-N
C-OC=Hs //

108 H -O-CF2-CF2-O- H H -O-n-C3H7 1H-NMR*):
5.75; 7.48; 7.54 109 H -O-CF2-CF2-O- H H-O-CH2-C=CH 1H-NNIIt*):
5.81; 7.49; 7.68 110 H -O-CF2-CF2-0- H H -CO-OC2H5 m.p.90 C
111 H -0-CF2-CF2-O- H CH3 -CO-OC2H5 1H-1VMR*):
5.84; 5:34; 7.65 .' 112 H ==O-CF2-CHF-O- H H -O-C2H5 1H-N1v1R*):
(=-o-CHF-CF2-o-) 5.84; 7.64; 7.71 113 H =-O-CF2-CHF-O- H H-O-CH(CH2F)2 IH-IVMR*):
(-o-CI-iP-CF2-O-) 5.81; 6.01;
7.35; 7.61 114 H -0-CF2-CHF-O- H H -O-n-C3H7 1H-NMR*):
(-O-CHF-CF2-O-) 5.70; 6.03;
7.50; 7.60 115 H -O-CF2-CHF-O- H H-O-CH2-C CH 1H-NMR*):
(-o-CHF-CF2-o-) 5.56; 6.00;
7.46; 7.54 LeA29088 -57-Ex. X1 X2 X3 X4 Rl R2 Physical No. Properties 116 H -0-CF2-CHF-0- H H CH 3 IH-NMR*):
(-O-CHF-CF2-O-) -N. 5.78; 6.01;
C-OC=HS
i~ 7.43; 7.57 117 H -O-CF2-CHF-0- H H ,q2Hs IH-NMR#):
(-O-CHF-CF2-O-) -N 5.80; 6.00;

7.45; 7.48 118 H -0-CF2-CHF-O- H H ,n-qH, IH-NMR*}:
(-O-CHF-CF2-O-) -N 5.85; 6.05;
C-OC=HS
ii 7.53-7.68 119 H -=0-CF2-CHF-O- H H -CO-OC2H5 1H-NMR*):
(=-O-CHF-CF2-O-) 4.98; 6.03;
7.09; 7.63 120 H -0-CF2-CHF-O- H CH3 -CO-OC2H5 IH-NMR ):
(-O-CCHF-CF2-O-) 1.86; 6.01;
7.19; 7.62 121 H -O-CF2-CClF-O- H H. -O-C2H5 IH-NMR*):
(-O-CCIF-CF2-O-) 2.35; 7.15-7.98 122 H -'0-CF2-CC1F-0- H H -O-n-C3H7 (-,D-CCIF-CF2-O-) LeA29088 -58-z148612 Ex. XI '(Z X3 X4 Rl R2 Physical No. Properties 123 H -0-CF2-CCIF-O- H H -O-CH2-C=CH
(-,O-CCIF-CF2-O-) 124 H -O\ c zO H H -O-C2H5 1H-NNIIt F3C' "CR,fF3 5.62; 7.28; 7.32 125 H -O\ C~' O- H H CH 3 1H-NMR*):
F3C' \CH2 -CFs C-OCHS A: 5.78; 7.32;
7.44 0 B: 5.80; 7.32;
7.44 126 H --O\, O- H H ,C2HS 1H-NMR s.
-]3C' CH2 ~F7 -N L-Q"3HS A: 5.76; 7.30;
~+
~i 7.42 0 B: 5.78; 7.30;
7.42 127 H --O\C'0~-- H H iN ~sK, 1H-i~iMR ):
Frs~ ~1:H2 CF3 A: 5.76; 7.32;
C--OqHs 7.42 0 B: 5.78; 7.32;
7.42 128 H CF-{O H H H -O-C2H5 (H) (CF30) 129 H CF-;O CF3O H H -O-C2H5 1H-NMR*):
5.50; 7.78; 7.82 LeA29088 -59-1214 ~ 6 1~

Ex. X1 ):2 X3 X4 Ri R2 Physical No. Properties 130 H CF3O CF3O H H -O-n-C3H7 IH-NMR*):
5.51; 7.75; 7.79 131 H CF'30 CF30 H H-O-CH2-CCH 1H-NMR#):
5.48; 7.76; 7.80 132 H CF'30 CF3O H H-O-CH(CH2F)2 1H-NMIIt*):
5.80; 7.78; 7.84 133 H C113-S02- H CF3 H -O-C2H5 1H-NMR*):
(CF3) (H) (CH3-S02-) (H) 5.80; 8.25; 8.56 134 H CF3 (CH3O) H H-O-C2H5 1H-NMR*):
(CH3O) CF3 A: 5.49; 7.05;
7.70 B: 5.50; 7.10;
7.73 135 H (C2H5)2N-CO- H H H-O-C2H5 1H-NMIt*):
(H) ((C2H5)2N-CO-) 5.73; 5.74;
7.29-8.63 (H) (C2H50-CO-) 5.72; 5.74;
7.65-8.59 137 H C6H,;-CO-NH- H H H -O-C2H5 1H-NNIIt*):
(H) (C6H5-CO-NH-) 5.70; 7.21-8.48;
7.98 138 H CH30-CO- H H H-O-C2H5 1H-NMR*):
(H) (CH3O-CO-) 5.72; 5.74;
7.68-8.59 LeA29088 -60-~14~~12 The following subsi:ituted benzimidazoles of the general formula (Ia) are additionally obtained in a corresponding manner:

a X. ~ N
~ C ~}-CF3 (la) X~ ~ N

Ex. No. X2 X3 Physical Properties 139 ~Iiz-OC2Hs H 1H-NMR*):
Cl cl )-CH= SiJz-N-C11; 5.69; 5.70;
ct ~, cH- so= N 7.03-8.05 p *):
140 \ ~>-Clij SOZ-NH- H IH-NMR
5.65; 5.67;
(H) 6.71-8:03 .
~- / Ci= 8p2-UH

141 CE;H5-SO2-NH- H
(H) (C6H5-SO2-NH-) 142 Ci H IH-NMR*):
C Cl 5.32; 5.63;
7.15-8.46 ~ / 90=-NH-LeA29088 -61 -21_496 12 Ex. X2 X3 Physical No. Properties 143 611 CF, HI H-NMR*):
~3 , 5.18; 5.63;
6.95-8.40 ~) 9J2-NH-I I
(CH3)3C-CH1 O-C- Q 5.81; 5.82;
II 7.65-8.62 (H) )iC-CFLi O-C

145 Cl 0 H 1H-NMR
Cl-(~ ~NH-C-NH- 62(Clo) ~ ~ NHC-NH- 6.78-8.15 146 F'~H o o H IH-NMR
IL 5.53;=6.45-8.07 Fc NIi-C-NH- F~~
FO O
II
(H) 0 < NH-c-NH-147 ci j 0 H 1H-NIv~t CiHsO-(CH=)=40--(~-)-NH-C-NH- CI O 5.51; 5.54;
' (~ c,H,o{cti,h ~NH-C-NH) 6.71-8.01 LeA29088 -62-Ex. X2 X3 Physical No. Properties 148 ci - H
-C,H,o{~; i NH-C-NH- Cl (H) II
(-c,R7o.<CN)r~NH-C-NH-C.iHsO{CHqk \~fNH-C-NH- 5.54; 5.58;
0 6.72-8.08 (H) II
CaI-IsO-(CHrv \ / NH-C-NH)-150 H 1H-NIVIIZ*):
H'o~(cx'~ \ / Nx-c-Nx- 5.49; 5.53;

(H) i-- H,o{CH,)i \ / NH-C-NH- 6.61-8.11 The 'H-NNIR. spectra were recorded in deuterochloroform (CDC13) or hexadeutero-d.imeth,yl sulphoxide (DMSO4) with tetramethylsilane (TMS) as the internal standard. The data given are the chemical shift as 8 value in ppm.

Le A 29 088 - 63 -Prepmation of the slbwrting comnound:

Example II-1:

-N
~-CF3 H ~---CF3 cr N
N
H
18.4 g(0.092 mol) of 3,4-diaminobiphenyl and 150 ml of trifluoroacetic acid are refluxed for 5 hours. Excess trifluoroacetic acid is subsequently distilled off, the residue is partitionect between 200 ml of ethyl acetate and 70 ml of water, the organic phase is separated off, washed with in each case 70 ml of saturated aqueous sodium hydrogen carbonate solution and water, dried over sodium sulphate and concent3ated in vacuo, and the residue is purified by chromatography over silica gel (eluent: cyclohexanelethyl acetate 2:1).

18.3 g (76% of theory) of 5(6)-phenyl-2-trifluoromethyl-1H benzimidazole as a 1:1 regioisomer mixture of melting point 177-182 C are obtained.

NH

88 g (0.4 mol) of 4-=ino-3-nitro-biphenyl (92 per cent) are hydrogenated with molecular hydrogen in 30(X) ml of inethanol in the presence of 10 g of Raney nickel at 60 C and a pressure of 5 bar. For working up, the Raney nickel is filtered off and the filtrate is concentrated in vacuo.

LeA29088 -64-___ 69.2 g (86% of theory) of 3,4-diaminobiphenyl of melting point 96-99 C are obtained (purity according to HPLC 92%).

NHZ

43 g(0.15 mol) of 4-acetamido-3-nitro-biphenyl (90 per cent) and 1.6 g (0.03 mol) of sodium methylate are refluxed for 2 hours in 500 ml of inethanol. For working up, the cooled reaction mixture is poured into 1300 ml of ice-water and stin-ed for 10 minutes, and the precipitate which has separated out is then filtered off with suction and dried.

33 g (94% of theory) of 4-amino-3-nitro-biphenyl of melting point 163-165 C
are obtained (purity according to HPLC 92%).

O
( ?-- NH-C\
~--' C H3 A mixture of 50.4 ml (1.2 mol) of 98 per cent strength nitric acid and 60 ml of glacial acetic acid is added dropwise with stimng at 70 C to a suspension of 84.4 g (0.4 mol) of 4acetamido-biphenyl (compare, for example, Beilstein Volume 12, 4th Supplement, p. 3248) in 340 ml of glacial acetic acid, and, when the addition has ended, the mixture is stiured for a further hour at 70 C. For working up, the cooled reaction mixture is poured into 1.00 ml of ice-water and stiired for 10 minutes, and the precipitate which has separated out is filtered off with suction, washed with 200 ml of water and dried.

L e A 29 088 - 65 -100 g (88% of theory;, of 4-acetamido-3-nitro-biphenyl of melting point 128-are obtained (purity according to HPLC 90%).

The following 1 H-benzimidazoles of the formula ~
X
z N
3~ I ~--CF3 X N
H
X

are obtained in a corresponding manner.
LeA29088 -66-2t 48 G 12 Ex. X1 X2 X3 X4 Physical No.
Properties II-2 Br H CF3 H mp.149-151 C
(H) (CF3) p (Br) 11-3 H H C6H5-CO- H mp.120-122 C
((,'6H5-CO-) (H) II-4 H CH3-CO- H H mp.145-149 C
(H) (CH3-CO-) II-5 H C1-CH2-S02- H H mp.197-200 C
(H) (CI-CH2-SO2-) 11-6 H -O-CH2-CH2-CH2-O- H mp. >230 C

(M (Ii3C-SO2-) 11-8 Br H C1-CH2-S02- H mp.180-187 C
(H) (C1-CH2-S02-) (H) (Br) 11-9 H CF3 Br H mp.209 C
(Br) (CF3) 11-10 H -O-CF2-O- H ni.p.242 C
II-11 H -O-CF2-CF2-0- H m.p.235-237 C
11-12 H -O-CF2-CHF-O- H mp.217 C
(-O-CHF-CF2-O-) 11-13 H -O-CFCI-CFCI-O- H m.p.185 C
11-14 H CF30 CI H mp.144 C
(Cl) (CF30) Ex.
No. X1 X2 X3 X4 Physical Properties II-15 H ~~~c "lo+ H mp.209 C
F,C' 'C'H2-CF3 11-16 H CF3O H H m,p,168 C
(H) (CF30) 11-17 H CF3O CF3O H m.p.158 C
11-18 H CH3-S02- H CF3 mp.105 C
(CF3) (H) (CH3-SO2-) (H) 11-19 H CF3 CH3O H m.p.60 C-(CH30) (CF3) 11-20 H (C2H5)N-CO- H H rrLp, 125 C
(H) ((C2H5)N-CO-) II-21 H C2H50-CO- H H mp.140 C
(H) (C2H50-CO-) 11-22 H C6H5-CO-NH- H H mp.*202 C
(H) (C6H5-CO-NH-) 11-23 H CH3O-CO- H H m.p.157 C
(H) (CH3O-CO-) 11-24 H (CH3)2N-CO- H H m.p, 226-227 C
(H) ((CH3)2N-CO-) 11-25 H F2CH-CF2-0- H H mp.181 C
(H) (F2CH-CF2-O-) 11-26 H C6H5-SO2-NH- H H mp, 70 C
(H) (C6H5-SO2-NH-) LeA29088 -68-Ex. XI X2 X3 X4 Physical No.
Properties II-27 H Cl H H
~-9o,-NH- Cl m.p.67 C
(H) ~ / 9J2-Nx II-28 H CF3 H H r3lp, 79 C

(H) C 902-NH-11 H H m.p.214-215 C
(3i3)3C-CH= O-C-O
(H) tl (CHAC-CHj-O-C-) II-30 H - ct 0 H H m.p.254-255 C
ct-~ / NH-c-NH-(H) EdHLH-Le ~14~~12 Ex. X1 X2 X3 X4 Physical NO= Properties 11-31 H F'C4;No 0 H H mp.103 C
FsC--~ II
O } NH C-NH-\ /
F,C-CH, O
II
(H) O\-/ 1VH-C-IVH-II-32 H c[ _ H H m.p. 186 C
C1H,()(CF~)i-G \ / NH-C-NH-cl O
(r-1-40.(CNk-G\ / MH-c11-NH)-11-33 H cl H H mp.144 C
nc,E[,accx, \ / rrH-C-rht-ct p l "'qH~C~ \ / ~-Cl-IiH-11-34 H = _ 0 H H mP= 207 C
~H:~=(c~h \ / rrH-C-r[x-~ (r-,,,0{cx,h O taH-C-rnt)-LeA29088 -70-~143612 Ex. X1 X2 X3 X4 Physical No.
Properties 11-35 H o ~-c,:",o{Clt,~ ~ / NH-c-NH- H H m.p.201 C

n iC- H7O(CH2), ~ / A1H-C-NH-11-36 H C, "~IOCH' H H m.p.80 C
CI- C/ (M1 S0= N

~N -or, CI ~ / CIii 9~1 ~
11-37 H (CF3)2N- H H
(H) ((CF3)2N-) II-38 H H m.p.68 C
(H) ~ ~ CEis 11-39 H CF3S H H m.p.174 C

(H) (CF3S) I1-40 H FC1CH-CF2-O- H H m.p.57 C
(H) (FCICH-CF2-O-) LeA29088 -71-Ex. X1 }(2 X3 X4 Physical No. Properties 11-41 H Cl= o H H m.p.176 C

Cl- ~NH-C-NH- Cl 0 (1-~ C ~ ~ (1NHNH) 11-42 H CH, so,-NH--O so,-rn-i- H H

01) ( II-43 H p H H m.p.190 C

~N1H-C-NH
I I

~~ (i a NH-OC-NH- 11-44 H _ 0 H H m.p.208 C

cH,O{CHA NH-c-NH--NH-Of) cH,O-,CNh ~NH-c LeA29088 -72-__ Ex. X1 X2 X3 X4 Physical No. Properties II-45 H yCH3)3C-O-CO- H H m.p.162 C
(H) ((CH3)3C-O-CO-) 11-46 H COOCH3 H H .p.70 C
SOz-NH- COOCH, (H) QH H
i:O
, NH-C-NH Cl O
\ II
~ , NH-C-NH-(M

I1-48 H ~--~ 0 H H m.p.61 C
02N--(, . >--C-NH- . 0 ~: II = .
~ 02N O C-NH- .

II-49 H QCNH H H m. p.76 C

C:L I I
C-NH-(R) C1 LeA29088 -73-2 t 4 3 6 12 ER= X1 X2 X3 X4 No Physical .
Properties 11-50 H (-'H,O-CP-N-9Jz-NH- H H
~H3 Ei3O=CO-N-87Z NH-~7 11-51 H COOH H H m.p.250 C
(H) (COOH) 11-52 H (CH3)3(:-NH-CO- H H m.p.79 C.
(H) ((CH3)3C-NH-CO-) II-53 H ~H ~ H H m.p.39 C
F',C-C-=NH-C-I

(H) ~H, 11-54 H A(C-CH2- H H
(H) (NC-CH2-) (H) (NH2) (H) (HOOC-CH2-) (H) (F3C-SO2-) The 'H-NMR. spectra were recorded in deuterochloroform (CDC13) or hexadeuterodimethyl sulphoxide (DMSO-d6) with tetramethylsilane (TMS) as the internal standard. The data given are the chemical shift as b value in ppm.

Chloro-(2-halogeno-1-fluoromethyl-ethoxy)-methanes of the formula Le A 29 088 - 74 -Ci-CH2-O-C\H

in which X represents fluorine or chlorine [Specifically, these are chloro-(2-fluoro-l-fluoromethyl-ethoxy)-methane (formula (I), X = fluorine) and chloro-(2-chloro-l-fluoromethyl-ethoxy)-methane (formula (I), X = chlorine).) can be obtained by rEmcting halogenated isopropanols of the formula .. . . . . .

HO-C\H

in which X represents fluorine or chlorine, with formaldehyde and hydrogen chloride at -20 to +20 C.
They can be used for the preparation of substituted benzimidazoles of the forrnula Le A 29 088 - 75 -;K

X N
X3 Y' N~--C F3 C H2X
~
4 CH2-O-C\H

in which X represent fluoi:-ine or chlorine and X', V, X3 and V independeritly of one another in each case represent hydrogen, halogen, cyano, nitro, in each case optionally substituted alkyl, alkoxy, alkylthio, al]icylsulphinyl, alkylsulphonyl or cycloalkyl, optionally substituted, fused dioxyalkylene; or hydroxycarbonyl, alkylcarbonyl;
alkoxycarbonyl, cycloEakyloxycarbonyl, in each case optionally substituted ami.no or arninocarbcinyl or in each case optionally substituted aryl, aryloxy, arylthio, arylsulphinyl, arylsulphonyl, arylsulphonyloxy, arylcarbonyl, aryloxyc:arbonyl, arylazo or arylthiomethylsulphonyl, but where at least one of the substituents X', V, X3 or V represents halogeno-alkyl wi.th the exception of the chloromethyl radical, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl, halogenoalkylsulphonyl, alkylsulphonyl, optionally substituted, fused dioxyalkylene, or hydroxycarbonyl, alkylcarbonyl, alkoxycarbonyl, cycloalkyloxycarbonyl, in each case optionally substituted amino or aminocarbonyl, or in each case optionally substituted aryl, arylthio, arylsulphinyl, arylsulphonyl, arylsulphonyloxy, arylcarbonyl, aryloxycarbonyl, arylazo or arylthio-methylsulphoriyl, from benzimidazoles of the formula LeA29088 -76-21~~~12 x x N
3 ~--C F3 x N
Example X H

192 g of 1,3-difluoro-2-propanol were treated with 66 g of paraformaldehyde (finely powdered). At -10 C, a vigorous stream of hydrogen chloride gas was then passed in, with stirring, until a clear 2-phase mixture had formed. The organic phase was subsequenitly separated off, dried using calcium chloride and subjected to fiactional distillation in vacuo. With a boiling point of 50 to 54 C at 20 mbar, 183 g(60% of theory) of chl~oro-(2-fluoro-1-fluoromethyl-ethoxy)-methane were obtained. The characteristic absorptions in the NMR spectra were as follows:
'H-NMR: 5.6 ppm and 4.55 ppm.
19F-NMR: -233 ppm.

Fluorinated 1,3-benz&-dioxoles of the forrrmula LeA29088 -77-R
Ft 2 4 3 R

in which X represents hydrogen, iluorine, chlorine or broniine and R' and R4 can be identical or different from each other and in each case denote hydrogen, halogen, C,-C6-alkyl, C,-C6-alkoxy, halogeno-C,-C6-alkyl, C6-C,o-aryl, COOI1, CN, NCO, COO-C,-C6-alkyl, NH-C,-C6-alkyl or N(C,-C6-alkyl)2, and RZ and R3 represent NO2 or NHZ, can be obtained by reacting 1,2-dihydroxybenzenes R
R2 ~ OH

3 ~ ~

R

in which R' to R4 have the abovementioned meaning, with hexafluorobutene of the formula Le A 29 088 - 78 -~14 86 12 , cis-trans in which X' represents hydrogen or halogen and ~ represents halogen, in the presence of a base and of a diluent at -20 to +200 C, or by first reacting 1,2-dihydroxybenzenes which have a protective group, of the formula R
R2 pRs R

in which R' to R4 have the ab)vementiioned meaning and RS represents a protective group or RS together with R' represents a-C(CH3)2-0- radical LeA29088 -79-with a hexafluorobutene of tlle formula cis-trans in which X' represents hydrogen or halogen and V represents hallogen, thus resulting in an intermediate of the formula R
R? OR5 R O-C =C
R' I X ~

in which R' to R4, RS and X' lqave the abovementioned meaning, eliminating the protective group RS from the intermediate of the above formula, and reacting the resulting OH compound with a base, thus obtaining 1,3-benzo-dioxoles of the above formula.

Le A 29 088 - 80 -1,3-Benzo-dioxoles which have two adjacent amino groups can be converted with trifluoroacetic acid tc- give the corresponding benzimidazole, for example of the following formula R

F=3C--~ I K
Ii O CHXCF3 ~
F

in which R', R4 and X have the abovernentioned meaning.

By alkylation, benzirnidazole. derivatives can be'obtained from these which are substituted on the niti ogen atom by a R
-CH radical.
Le A 29 088 - 81 -21.4--8612 Examples E-x=le 1 a 2-(2,2,2-Trifluoroethyl)-2-trifluoromethyl-1,3benzodioxole 11 g of pyrocatechol were (fissolved in 200 ml of dimethylformamide and the solution was treatecl with 1.8 g of 45% strength by weight aqueous sodium hydroxide solution. The mixture was treated dropwise at 75 C with 20 g of 2-chloro-1,1,1,4,4,4-hexafluoro-2-butene. Stirring was continued for 30 minutes at 75 C. The batch was subsequently poured into 500 ml of ice-water and extracted using diethyl ether. The organic phase was washed with water, dried with magnesium sulphate and concentrated. Finally, the product was distilled under a high vacuum. The yield was 15 g(=56 ,/o), and the boiling point 60 C at 10 mbar.
The NMRspectra- showed the following characteristic ab sorptions: 19F-1VNIR: -59.0 and -84.6 ppm. 'H-NMR 3.02 ppm.

Ex=le 2a 2-(1-Chloro-2,2,2-triiluoroethyl)-2-trifluoromethyl-1,3-benzodioxole 110 g of pyrocatechol were dissolved in 1500 ml of acetonitrile, and the solution was treated with 200 g of trielhylamine. The mixture was treated dropwise at with 235 g of 2,3-dichloro- 1,11,1,4,4,4-hexafluoro-2-butene. Stirring was continued for 2 hours at 75 C.1200 ml of the solvent were subsequently distilled off in vacuo, and the residue was taken up i.n 1500 ml of water. The product was extracted using diethyl ether, and the organic phase was washed twice using 10%
strength by weight aclueous sodium hydroxide solution and once with water.
After drying with magnesium sulphate, the organic phase was concentrated and subjected to fractional distillation in vacuo. The yield was 258 g (= 84% of theory).
The boiling point was 6:3 C at 12 mbar. The NMR spectra showed the following L.eA29088 -82-~14-8 6 1 w characteristic absorptions: '9F-NMR: -66.8 and -79.7 ppm. 'H-NMR: 4.71 ppm.
Examples 3a 2-(1,1,1,4,4,4-Hexafluoro-2-butenoxy)-methoxybenzene 260 g of 2-methoxyphenol were dissolved in 1 1 of dimethylformamide (technical grade) and the solution was treated with 220 g of 45% strength sodium hydroxide solution. 400 g of 2-chloro-1,1,1,4,4,4-hexafluoro-2-butene were then added dropwise with stirring at 22 C:. Stirring was continued for 2 hours up to 22 C. The mixture was then txezted with 1.5 1 of ice-water and extracted with methylene chloride.

The combined organic phases were washed twice using 10% strength sodium hydroxide solution and once using saturated NaCI solution, dried using MgSO4 and distilled. The yield was 329 g (58% of theory), and the boiling point was 68-at 12 mbar. The NMR spectra showed the following characteristic absorptions:19F-NMR -57.6 and -67.9 ppm. 'H-NMR: 5.92 ppm.

Bxamnle 4a 2-(1,1,1,4,4,4-Hexafluoro-2-butenoxy)-phenol 286.1 g of 2-(1,1,1,4,4,4-hexa.fluoro-2-butenoxy)-methoxybenzene of Example 3a were dissolved in a rnixture of 500 ml of glacial acetic acid and 500 ml of 48%
strength hydrobromi.c acid, and the mixture was treated with 5 g of triethylbenzylammonium chloride. The mixture was stirred at a bath temper=ature of 150 C until a gas-chroniatographic check showed that the reaction was complete. The mixture was then allowed to cool and treated with 2 kg of ice-water. The aqueous phase was extracted thoroughly using CH2C12. After drying with MgSO4, the solvent was stripped off and the residue distilled in vacuo.
The Le A 29 088 - 83 -yield was 200 g(50 'o of theory), and the boiling point was 80 C at 16 mbar.
The NMR spectra showed the following characteristic absorptions: 14F-NMR: -59.6 and -69.6 ppm. 'H-NMR: 6.1 ppm.

Exa nr ple 5a 2-(2,2,2-Trifluoroethyl)-2-trifl.uoromethyl-1,3-benzodioxole 200 g of 2-(1,1,1,4.,4,4-Hexafluoro-2-butenoxy)-phenol of Example 4a were dissolved in 400 ml of acetonitrile and the solution was treated with 5 g of triethylamine. The mixture mias stirred for 4 h at 70 C. It was then distilled in vacuo. The yield was 162 g (81% of theory), and the boiling point was 60 C at 10 mbar. The NMR spectra showed the following characteristic absorptions: 19F-NMR: -59.0 and -84.6 ppm. 'H-NMR 3.02 ppm.
~Aa=le 6a 2-(2-Chloro- 1,1,1,4,4,,4-hexafluoro-2-butenoxy)-1-benzyloxybenzene 20 g of 2-benzyloxyphenol were dissolved in 100 ml of dimethylformamide and the solution was treated with 9 g of 45% strength sodium hydroxide solution.
23 g of 2,3-dichloro-1,1,1,4,4,4-hexafluoro-2-butene were then added dropwise at room temperature. After the exothermic reaction had subsided, stining was continued for 1 hour at room temperature. and the mixture was poured into water and extracted using tert.-butyl methyl ether. After drying with MgSO4, the solvent was stripped off. The yield was 29 g (74% of theory). The NMR spectra showed the following characteristic absorptiions: 'vF--NMR -59.5; -60.5; -61.7 and -62.8 ppm.
LeA29088 -84-Exa=le 7a 2-(2-Chloro- 1,1,1,4,4~,4-hexafluoro-2-butenoxy)-phenol 24.4 g of 2-(2-chloro- 1,1,1,4,4,4-hexafluoro-2-butenoxy)-1-benzyloxybenzene of Example 6a were diissolved in 150 ml of tetrahydrofuran and the solution was treated with 3 bar hydrogen for 4 hours at room temperature in the presence of 2 g of Pd/C (10% strength). The imixture was subsequently filtered and the filtrate was concentrated and distilled in vacuo. The yield was 13.2 g (69% of theory), and the boiling point was 56 C at 0.15 mbar.

F&=le 8a 2-(1-Chloro-2,2,2-triiliuoroethyl)-2-trifluoromethyl-1,3-benzodioxole . , .

11.7 g of 2-(2-chloro-1,1,1,4,4,4-hexafluoro-2-butenoxy)phenol of Example 7a were dissolved in 40 ml of tert.-butyl methyl ether and the solution was treated with 40 ml of 1N sodium hydroxide solution. After the mixture had been stirred for 30 minutes at room temperature, the organic phase was separated off, dried using MgSO4 and distilled. The yield was 10 g (88% of theory), and the boiling point was 63 C at 12 mbar. The NMR spectra showed the following characteristic absorptions: '9F-NM1Z -66.8 and -79.7 ppm. 'H-NMR: 4.71 ppm.

Ex le 2,2-Dimethyl-4-(1,1,11,4,4,4-hexafluoro-2-butenoxy)-1,3-benzodioxole (Formula V, RS together with R' == -C(CH-3)2-0- radical) 46 g of 2,2-dimethyl-4-hydroxy-l,3-benzodioxole (Formula IV, RS together with R3 =-C(CH3)2-0- radical) were dissolved in 200 ml of N-methylpyrrolidone and the solution was treated widt 31 g of 40% strength by weight aqueous sodium LeA29088 - 85 -hydroxide solution. 54.8 g of 2-chloro- 1, 1, 1,4,4,4-hexafluoro-2-butene were subsequently added dropwise at room temperature with stin-ing. Stirring was continued for 1 hour, and the batch was then poured into water and extracted using tert.-butyl methyl ether. The organic phase was washed using 10% strength by weight aqueous sodilun hydroxide solution and dried using magnesium sulphate, and the readily volatile components were removed on a rotary evaporator. This gave 73.8 g (= 80% of theory) of a product whose purity was 95% according to gas chromatography. The characteristic absorptions in the NMR spectra were:

NMR: -58.1 and -68.5 ppm. 'H-NMR: 6.73, 6.55, 6.03 and 1.70 ppm.
Exanmle l0a 1,2-Dihydroxy-3-(1,1,1,4,4,4-hexafluoro-2-butenoxy)-benz.ene 65 g of the product of Example 9a and 200 nil -of concentrated aqueous hydrochloric acid were. refluxed for 4 hours with stimng. The batch was subsequently diluted with 300 ml of water and extracted using methylene chloride.
After drying with rriagnesiutn sulphate, the solvent was stripped off from the organic phase, giving 54 g of a product of 90% purity. Recrystallization from cyclohexane gave o:)lourless crystals having a melting point of 105 C. The characteristic absorptions in the NMR spectra were as follows: 'gF-NMR -57.7 and -67.7 ppm. 'H-NMR: 6.77, 6.50, 6.21 and 5.42 ppm.

Exam in e 11 a 2-(2,2,2-Trifluoroeth)/l)-2-(trifluoromethyl)-4-hydroxy-1,3-benz,odioxole (Formula (I), R' =OH, X=H., A=CH, RZ andR3=H) 43.5 g of the product of Example l0a were dissolved in 300 ml of acetonitrile, and 1.5 g of triethylamine were added at room temperature. After the mixture had been stirred for 2 hours at room temperature, the solvent was stripped off and the Le A 29 088 - 86 -2 ~ 0~~2 residue was distilled in vacuo. The yield was 17 g (= 39% of theory), the boiling point was 85 C at 0.15 mbar, and the melting point was 65 C. The characteristic absorptions in the NlvIR spectra were as follows: 19F-NMR -59.0 and -84.5 ppm.
'H-NMR: 6.80, 6.55, 6.2 and 3.01 ppm.
Examnle 12a 2,2-Dimethyl-4-(3-chloro-1,1,1,4,4,4-hexafluoro-2-butenoxy)-1,3-benzodioxole (Formula (V), R' and RS together are -C(CH3)2-0-, X' = Cl, R2 + R3 = H, A =
CH) 33.2 g of 2,2-dimeth.yl-4-hydroxy-1,3-benzodioxole were reacted analogously to Example 9a with 47 g of 2,3-dichloro- 1, 1, 1,4,4,4-hexafluoro-2-butene. The product obtained was distilled in vaci.io, and a 1:1 molar mixture of cis/transisomers was obtained. The yield was 51 g70%0 of theory), and the boiling point was 70 C
at 0.15 mbar. The characteristic absorptions in the NMR *spectra were as follows:
19F-NIVIR: -60.0, -61.6, -62.2 and 63.4 ppm. 'H-NMR: 6.79, 6.65 to 6.48 and 1.7 ppm Exam in e 13a 1,2-Dihydroxy-3-(3-chloro-1, ]1,1,4,4,4-hexafluoro-2-butenoxy)-benz.ene (Formula (V),R'=OH,RZ+R3=H,A=CH,RS=H,X'=Cl) 18 g of the product of Example 12a were reacted analogously to Example 1 Oa with 50 ml of concentrated hydrochloric acid. 15.7 g of a product with a purity of 97%
were obtained. The product was a 1:1 molar mixture of the cis/trans isomers.
The characteristic absorptions in the NMR spectra were as follows: 19F-NMR: -60.2, -61.3, -62.2 and -63.3 ppm. '1:-1-NNIR: 6.80, 6.45 and 6.25 ppm.

Le A 29 088 - 87 -Example 14a 2-(1-Chloro-2,2,2-trifluoroethyl)-2-trifluoromethyl-4-hydroxy-1,3-benzodioxole 15 g of the product of Examp;le 13a were dissolved in 50 ml of acetonitrile and the solution was treated with 1. rni of triethylamine. The mixture was stiirred for 15 niinutes, the solvent was then. stripped off, and the residue was distilled in vacuo.
For purification, the product was taken up in diethyl ether and filtered through silicon dioxide. After the diethyl ether had been stripped off, 10.5 g of the product (= 70% of theory) remained. The melting point was 139 to 141 C. The characteristic absorptiions in tl:ie NMR spectra were as follows: 19F-NMR: -66.6 and -79.3 ppm. 'H-NMR 8.4, 6.76, 6.60, 6.50 and 4.70 ppm.

Exain~le 15a .15 .
5-Nitro-2-(2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxole A solution of 54.4 g of 2-(2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxole in 75 ml of methylene chloride was added dropwise at 10 C to a mixture of 40 ml of 65% strength by weight nitric acid and 40 ml of concentrated sulphuric acid.
Stirring was contiinufA for 1 hour at room temperature and the batch was then poured into ice-water, the organic phase was separated off, and the aqueous phase was extracted using methylene chloride. The combined organic phases were washed with water, dried and freed from volatile components. 95 g of the product (= 86% of theory), which hacl a melting point of 87 to 88 C, remained.
The NMR spectra showed the following characteristic absorptions: 19F-NIVIR -59.0 and -69.4 ppm. 'H-NMR: 3.10 ppm.

LeA29088 -88-21.48612 Examnle 16a 5-Nitro-2-(1-chloro-2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxole 613 g of 2-(1-chloro-2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benz.odioxole of Example 2a were dissolved in 1.2 1 of methylene chloride and the solution was added dropwise at 0 to 10 C to a mixture of 400 ml of 65% strength nitric acid and 400 ml of conceritraterl sWphuric acid. Stirring was continued for 2 hours at room temperature. Then, the rr,iixture was poured carefully into 2 1 of ice-water and extracted using methylene chloride. The combined organic phases were washed twice using water, dried and c:oncentrateri. The yield was 652 g (93% of theory).
The NMR spectra showexi the following characteristic absorptions: 19F-NMR -66.4 and -79.2 ppm. 'H-NTvIR 4.81. ppm.

Eyle 17a 5,6-Dinitro-2-(2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxole 317 g of the product of Example 15a were introduced, and a mixture of 250 ml of 100% strength by weight nitric acid and 350 ml of concentrated sulphuric acid were added dropwise, with stirring. The mixture was stirred for 2 hours at 55 C.
The batch was then allowed to cool and poured into ice-water. The product was extracted using methylene chloride, and the methylene chloride phase was washed until neutral using sodium hiydrogencarbonate solution, dried and freed from readily volatile components on a rotary evaporator. The yield was 339 g (= 94%
of theory), and the melting point was 101 to 103 C.

"Ihe NMR spectra showed the following characteristic absorptions: 'gF-NNIR: -60.9 and -86.5 ppm. 1H-Nl'dR 3.18 ppm.

L e A 29 088 - 89 -Exam lp e 18a 5,6-Dinitro-2-(1-chloro-2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxole 352 g of 5-nitro-2-(1-chloro-2.,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzod.ioxole of Example 16a were introduced and treated with a mixture of 250 ml of 100%
strength by weight nitric aciLd and 350 ml of concentrated sulphuric acid. The mixture was sti;rred iFor 2 hoiurs at 60 C. After cooling, the mixture was poured into ice-water and extracted using methylene chloride. The methylene chloride phase was washed with sodium hydrogencarbonate solution and dried and then evaporated on a rotary evapoirator. The yield was 392 g (91% of theory), and the melting point was 125 C. Th.e NMR spectra showed the following characteristic absorptions: 19F-NMR -68.5 and -81.0 ppm. 'H-NMR: 4.86 ppm.

.. ~'E&=le 19a 5-Amino-2-(2,2,2-trifluoroethyl)-2-trifluoromethyl-1, 3-benzodioxole 57.4 g of the product of ExanTle 15a were dissolved in 400 ml of tetrahydrofuran and hydrogenated wirh hydrogen for 5 hours at 30 C at 50 bar in the presence of 4 g of catalyst (palla(hum on charcoal, 10% strength by weight). The mixture was then subjected to filtration, the solvent was removed and the residue was distilled under a high vacuurn. Thi:s gave 37 g of product (= 63% of theory) having a boiling point of 83 C at 0.07 mbar. '9F-NMR: -59.0 and -84.6 ppm. 'H-NMR:
2.98 ppm.

Example 20a 5-Amino-2-(1-chloro-2,2,2-trifluoroethyl)-2-trifluoromethyl-1, 3-benzodioxole 72 gof5-nitro-2-(1-crdoro-2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxole LeA29088 -90-~ 14-8 6 .t 2 of Example 16a were dissolved in 500 ml of tetrahydrofuran and hydrogenated for hours at room temperature with 15 to 20 bar hydrogen using 5 g of palladium on charcoal (5% strength). The mixture was subsequently filtered and the solvent was stripped off in vacuo. The yield was 60 g (93% of theory), and the boiling point 5 was 80 to 82 C at 0.1 mbar. Zhe NMR spectra showed the following characteristic absorptions: 19F-NMR -66.5 and -79.4 ppm. 'H-NMR: 4.68 ppm.

Exarnple 21 a 5,6-Diamino-2-(2,2,2.-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxole 339 g of the product of Example 17a were dissolved in 2000 ml of tetrahydrofuran and treated with 20 g of catalyst (palladium on charcoal, 5% strength by weight).
The mixture was hydrogenated with hydrogen for 13 hours at 25 to 30 bar and at room temperaturE. The batch was then filtered and the solvent was stripped off iii vacuo. A solid remained. The yield was 274 g (= 96% of theory). 19F-NMR -61.2 and -86.6 ppm. 'H-NMR: 3.02 ppm.

Ex mple 22a 2-(2,2,2-Trifluoroeth)il)-2-trifluoromethyl-1,3-benzodioxole 306.5 g of 2-(1-chloro-2,2,2-irifluoroethyl)-2-trifluoromethyl-1,3-benzodioxole of Example 2a were dissolved in 500 ml of THF and the solution was treated with 101 g of triethylamine and 30 g of palladium on charcoal (5% strength by weight).
The mixture was then hydrogenated for 48 hours at 110 C under 100 bar hydrogen. The mixtw-e was subsequently filtered, the solvent was stripped off, and the residue was subjected to f actionation in vacuo. The yield was 126 g (46%
of theory), and the boil'vig point was 60 C at 10 mbar. The NMR spectra showed the following characteristic absorptions: 19F-NMR: -59.0 and -84.6 ppm. 'H-NMR:
3.02 ppm.

LeA29088 -91 -Fluoroalkyl(ene) group-containing o-phenylenediamines of the formula I

NHR

X
in which R' represents CF_,, OCF3, SCF3, S02-C,-C6-alkyl, which can be straight-chain or branched and fully or partially substituted by fluorine, N(CF3)2, a phenyl or phenoxy radical with CF3 or CN in the 4-position and, if appropriate, other substituents, 1,1õ2,3,3,3-hexafluoropropoxy, 1,1,2-trifluoro-2-chloro-ethoxy, 1,1,2,2-tetrafluoroethoxy, 1,1,2-trifluoro-2-chloro-ethylthio or 1,1,2,3,3,3-hexafluoropropylthio, R2 independently of R' represents F, Cl, Br, CN, CH3, OCF3, SC~-Cl-C6-alkyl, which can bestraight-c:hain or branched and fully or partially substituted by fluorine, Ci:)O-C,-C16-alkyl, COOC65, 1,1,2,2-tetrafluoroethoxy, 1,1,2,3,3,3-hexafluoropropoxy or 1,1,2-trifluoro-2-chloro-ethoxy and R3 represents hydrogen, CCCH3 or COCF3, it being possible for R' and R? together to represent a-4-CFCl-CFCI-O-radical, with the exception of the compounds described in EP-A 251,013 and EP-A 487,286, can bel obtained by dinitrating a benzene derivative of the formula D

Ds LeA29088 -92-in which D' represents CF30, CF3S, CHF2CF2O, CHFCI-CF2O, CF3CHFCF2O, CF3CFZO, CF3CF2CF2O, CF3CF2S or CF3CHFCF2O and D2 represents CF3O, ClF3S, CHF2CF2O, CHFCI-CF2O, CF3CHF-CF2O, CF3CF2O, CF3CF2CF2O, CF3CF2S, CF3CHFCF2O, fluorine, chlorine, bromine, C,-C6-alkyl or C,-C6-alkoxy, subsequently reducing the nitro groups and thus obtaining compounds in which R' and R2 are in the 4- and 5-position relative to the amino groups and have the meanings of D' and U.

If it is desired to prepare compounds in which R' has the abovementioned meaning and is in the 4-position relative to the amino groups and R2 represents Cl or Br in the 5-position relative to the aulvno groups, it is possible, for example, to react a nitrobenzene derivative of the formula I
R 20 Cl or in which R' has the abovernentioned meaning and Hal represents fluorine, chlorine or bromine, with ammonia to exchange the Hal group for an amino group, and to reduce the resulting nitraniline.

LeA29088 -93-4 Z 14 86?2 If it is desired to prepare compounds in which R' has the abovementioned meaning and is in the 4-position relatiive to the amino groups, R2 represents chlorine or bromine in the 6-position relative to the amino groups and R3 denotes hydrogen, it is possible, for example, to react a nitraniline of the formula R NOZ
~

in which R' has the aboveinentionexi meaniing.

with a chloriinating or brominatiing agent thus introducing a chlorine or bromine atom into the meta-position relative to the nitro group, and subsequently to reduce the nitro group.

If it is desired to prepare compounds in which R' denotes a donor group in the 4-position relative to the two amino groups, R2 denotes an acceptor group, for example COO-C,-C6-alkyl, CN, CF3 or SC2-C,-C6-a.lkyl and R3 is other than hydrogen, it is possible, for example, to mononitrate a benzene derivative of the formula D

A
in which LeA29088 -94-D' has the abovementioned meaning and A represents CF, S02-Ci-C6-alkyl, which can be straight-chain or branched and fully or partially substituted by fluorine, or represents COO-C,-C6-alkyl or CN, (the NO2 group enters in the para-position relative to D'), to reduce the NO2 group to the NH2 group, to acylate the NH2 group, for example with acetic acid or trifluoroacetic acid, to cany out another mononitration reaction (this NO2 group enters in the ortho-position relative to the NHCOR group in which R is, for example, CH3 or CF3), to reduce this NO2 group to the NH2 group and, if appropriate, if it is desired to prepare a compound of the above formula where is hydrogen, to elimiriate the acyl group by hydrolysis.

The fluoroalkyl(ene)-group-comtairiing o-phenylenediamines in which R3 denotes hydrogen can be initially reacted with trifluoroacetic acid to give 2-trifluoromethylbenzimidazoles of the formula R
N
~ ~--C F3 N
R H

and these can then be reacted further with compounds of the formula R
/
A-CH

in which R' and R2 assume the scope of the above meanings, Le A 29 088 - 95 -~143612 R4 represents hydrogen, alkyl, alkoxy or optionally substituted aryl, RS represents hydroxyl, cyano or in each case optionally substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, amino, aminocarbonyl, alk~ylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, dialkoxyphosphonyl, (hetero)aryl, (hetero)arylcarbonyl, (hetero)aryloxycarbonyl, (hetero)arylc.arbonyloxy or (hetero)arylamino-carbonylaminocarbonyloxy and A denotes a suitable leaving group.

Leaving groups are known to a person skilled in the art, examples being halogen, alkyl(alkoxy, aryl)sulphonyloxy, hydroxyl or alkoxy.

Em=les Exmples lb to 6b (Dinitration and reduction) Exam. ln e 1 b 320 g of 1,2-bis-(2-cl-Aoro- 1,1,2-trifluoroethoxy)-benz,ene were added dropwise to 500 g of a mixed acici containing 33% strength by weight HNO3 and 67% strength by weight H2SO4. After one hour at 40 C, 250 ml of 20% strength by weight oleum were added dropwise. 1he mixture was subsequently heated at 80 C, and stining was continuol for 15 hours. A further 120 ml of 20% strength by weight oleum and 250 g of the abovementioned mixed acid were then added dropwise.
After 6 hours at 80 to 82 C, the mixture was cooled and poured onto ice. The organic phase was separated off and washed with water. After azeotropic drying using 1,2-dichloroetliane, 350 g of 96% by weight pure 1,2-dinitro-4,5-bis-(2-chloro-1,1,2-trifluoroethoxi~)-benzene were obtained (oil, np : 1.4832, GC
99.1%) LeA29088 -96-~14312 350 g of this dinitro compoiund were added dropwise to a mixture of 1.5 1 of ethanol, 50 ml of water, 30 ml of concentrated aqueous hydrochloric acid and 470 g of iron filings, and the mixture was refluxed for a total of 15 hours.
When cold, the solution was filtered and concentrated and the residue was recrystallized from cyclohexane. 216 g of 1,2-diamino-4,5-bis-(2-chloro-1,1,2-trifluoroethoxy)-benzene having a melting point of 58 to 60 C were obtained.

E&=le 2b Analogously to Exarnple 1, :1,2-bis-(1,1,2,3,3,3-hexafluoropropoxy)-benzene was used to prepare the oarresponding 4,5-dinitro compound (oil, nD : 1.4852) and the corresponding 4,5-diamino compound (oil, 87% by weight pure).

Ex~le 3b Analogously to Example 1, 1-(1,1,2-trifluoro-2-chloroethoxy)-2-chlorobenzene was used to prepare the corresponcling 4,5-dinitro compound (melting point 56 to 57 C) and the corresponding 4,5-diamino compound (melting point 67 to 68 C).

x 4b Analogously to Example 1, 1-trifluoromethoxy-2-bromobenzene was used to prepare the corresponding 4,5-dinitro compound (melting point 73 to 75 C) and the corresponding 4,5-diamino compound (oil, purity 98% by weight, nD : 1.5485).
EAa=1e 5b Analogously to Example 1, 1-trifluoromethoxy-2-chlorobenzene was used to prepare the corresponding 4,5-dinitro compound (melting point 55 to 56 C) and the corresponding 4,5-diamino compound (melting point 56-57 C).

LeA29088 -97-Ex=le 6b 1-(1,1,2,3,3,3-Hexafluoroprop)xy)-2-chloro-benzene was used to prepare the corresponding 4,5-dinitro compound (oil) and the corresponding 4,5-diamino compound (oil).

Examnles 7b to 12b Treatment with ammonia under pressure and reduction Examnle 7b 260 g of 3-nitro-2,5-dichlorobenzotrifluoride, 130 ml of water and 10 g of tetraethylammonium chloride were introduced into an autoclave, and 120 ml of liquid ammonia were injected.. The mixture was then heated to 130 C and stirred for 10 hours at this temperature. After cooling, the batch was filtered and the precipitate which had been separated off was washed with water and dried 194 g of 2-amino-3-nitro-5-chloro-bmzotrifluoride with a melting point of 67 C were obtained.
134 g of the nitranil'uie obtained as described above were dissolved in 800 ml of ethanol, and 20 ml of water, 10 ml of concentrated aqueous hydrochloric acid and 160 g of iron filings were then added. The mixture was refluxed for 15 hours and then cooled, and subjected to filtration with suction, the filter residue was washed with dichloromethane, and the organic phases were subsequently freed from the solvent under reduced pressure. 171 g of 5-chloro-3-trifluoromethyl-1,2-diaminobenzene with a melting point of 53 C were obtained.

Exam le Analogously to Example 7, 3-nitro-4,6-dichloro-difluorochloromethoxybenzene was LeA29088 -98-~~~~6-IL 2 used to obtain fust 3-niilro-4amino-6-chloro-difluorochloromethoxybenz.ene (melting point 73 C) and therefrom 3,4-diamino-6-chloro-difluorochloromethoxy-benzene (oil).

F~=le 9b Analogously to Exarnple 7, 3-bromo-5-nitro-6-chlorobenzotrifluoride was used to prepare fust 3-bromo-5-riitro-i5-amino-benzotrifluoride (melting point 80 to 82 C) and therefrom 3-bronio-5,6-diamino-benzotrifluoride (melting point 52 to 54 C).
E&=le lOb Analogously to Exarr.iple 7, 3--cyano-4-chloro-5-riitro-benzotrifluoride was used to prepare first 3-cyano-4-amino-S-riitro-benzotrifluoride (melting point 99 to 100 C) and therefrom 3-cyano-4,5-diamino-benzotrifluoride.

Em=le llb Analogously to Example 7, 3,6-dichloro-5-nitro-benzotrifluoride was used to prepare first 3-chloro-5-riitro-6-amino-benzotrifluoride (melting point 53 to 54 C) and therefrom 3-chloro-5,6-diamino-benzotrifluoride.

Exam in e 12b 2-Bromo-4-fluoro-5-ndtro-(1,1,2-trifluoro-2-chloro)-ethoxybenzene was used to prepare fust 2-brorno-4-amiino-5-nitro-(1,1,2-trifluoro-2-chloro-ethoxy)-benzene (melting point 90 C) and thereirom 2-bromo-4, 5-diamino-(1,1,2-trifluoro-2-chloro)-ethoxybenzene.

LeA29088 -99-Exam (Halogenation of a niltianiline and reduction) 24 g of finely pulverulent 2-nitro-4-trifluoromethylmercaptoaniline were dissolved in 50 ml of tri-fluoroacetic acid, and 18 g of bromine were metered in at 20 C.
Stirring was then continued for 3 hours at 20 C and for a finther 30 minutes at 40 C. The mixture poiured into water and the product taken up in dichloromethane.
After the solvent had been removed, 31 g of 6-bromo-2-nitro-4-trifluoromethyl-mercapto-aniline were: obtained.
155 g of the nitranilvle thus prepared were refluxed for 15 hours with 15 ml of water, 10 ml of conce:ntrated aqueous hydrochloric acid and 70 g of iron filings in 700 ml of ethanol, the mixture was then filtered, the filtrate was freed from the solvent under reduced pressure and the solid crude product was recrystallized from cyclohexane. 112 g of 6-bromo-4-trifluoromethyl-mercapto-1;2-diaminobenzene with a melting point of 60 to 61 C were obtained.

mple 14b Ex Analogously to Example 13, 27 g of 2-nitro-4-trifluoromethyl-sulphonylaniline in 100 ml of acetic acid were brominated with 18 g of bromine.

After working up, 32 g of 2-nitro-6-bromo-4-trifluoro-methylsulphonyl-anialine were obtained. Melting point 147 C.
32 g of the nitramine thus prepared were reduced with iron filings in alcohol and aqueous hydrochloric acid. 24 g of 3-bromo-5-trifluoromethylsulphonyl-phenylene-1,2-diamine were obtained, melting point 155-157 C.

LeA29088 - 100-214~~~2 Examnle 15b Analogously to Example 14, 27 g of 2-nitro-4-trifluoromethylsulphonyl-aniline in 100 ml of acetic acid were chlorinated with 10 g of chlorine. 29 g of 2-nitro-4-trifluoromethylsulphonyl-6-chloro-aniline were obtained, melting point:
138-139 C.

13 g of 3-chloro-5-triifluoromethylsulphonyl-1,2-phenylenediamine (melting point:
143-145 C) were obtained by reduction.
Ex=les 16 to 20 (Nitration and reduction in 2 steps) Agij?n1e 16 263 g of 4-(2,6-dichloro-4-tri:fluoromethyl)-phenoxy-acetanilide were dissolved in 1100 ml of dichloromethane and introduced at 10 C. 88 g of 98% strength by weight nitric acid were theni added dropwise at this temperature. Stirring was continued for 1 hour at 10 C and for 2 more hours at 30 C. After 300 ml of water had been added, the phases were separated and the organic phase was freed from dichloromethane under reduced pressure. 253 g of 2-nitro-4-(2,6-dichloro-4-trifluoromethylphenoxy)-aaetanilide with a melting point of 138-140 C
remained.

91 g of the acetanilid.e thus pi=epared were dissolved in 800 ml of dioxane, 10 g of Raney nickel were added, and the mixture was hydrogenated at 25 to 45 C in a hydrogenation apparatus with a maximum hydrogen pressure of 50 bar. After releasing the pressure and filtration, the dioxane was distilled off under a slight vacuum. 65 g of 2-,amino-4-=(2,6-dichloro-4-trifluoromethyl-phenoxy)-acetanilide with a melting point of 222-223 C remained.

LeA29088 - 101 -E}cample 17 Analogously to Exarrple 16, 3-trifluoromethyl-4-methoxy-acetanilide was used to prepare first 3-trifluoromelhyl-4-methoxy-6-nitro-acetanilide (melting point 143-144 C) and therefrom 3-trifluoromethyl-4-methoxy-6-amino-acetanilide (melting point 164-165 C).

Example 18 Analogously to Example 16, 3-trifluoromethyl-4-fluoro-trifluoromethylacetanilide was used to prepare first 3-trifluoromethyl-4-fluoro-6-nitro-trifluoromethylacetani-lide (melting point 78 C) and therefrom 3-trifluoromethyl-4-fluoro-6-amino-trifluoromethylacetanilide (me;lting point 92-93 C).

Exa=1e.19.

Analogously to Exarr.ple 16, 3-trifluoromethyl-4-bromo-trifluoromethylacetanilide was used to prepare first 3-trifluoromethyl-4-bromo-6-nitro-trifluoromethyl-acetanilide (melting point 110 to 112 C) and therefrom 3-trifluoromethyl-4-bromo-6-amino-trifluorometlrylacetardlide (melting point 63-65 C).

Fy ,a=le 20 Analogously to Example 16, 3-trifluoromethylthio-4-chloro-tri-fluoromethylacetanilide was used to prepare first 3-trifluoromethylthio-4-chloro-6-nitro-trifluoromethylacetanillide (melting point 99-100 C) and therefrom 3-trifluoromethylthio--4-chloro-6-amino-trifluoromethylacetanilide (melting point 88-90 C).

Le A 29 088 - 102 -Example 21 0.2 mol of 3-brorno-5-trif.luoromethyl-phenylene-diamine and 150 ml of trifluoroacetic acid were refluxed for 3 hours. For working up, excess trifluoroacetic acid was distilled off and the residue was partitioned between 100 ml of water and :300 ml of ethyl acetate. The organic phase was separated off, washed in succession with in each case 100 ml of aqueous sodium hydrogencarbonate solution and water, dried over sodium sulphate and concentrated in vacuo. The residue was purified by chromatography on silica gel (eluent: cyclohexanelethyl acetate 1:1).
This gave 4-bromo-6-trifli,ioromethyl-2-trifluoromethyl-1H benzimidazole of melting point 149-151 C.

le 22 0.03 mol of 4-bromo-6-trifluoromethyl-2-trifluoromethyl-1H benzimidazole and 0.06 mol of pulverulient pot2issium carbonate were refluxed for 15 minutes in 70 ml of ethyl acetate, 3.9 g(0.04 mol) of chloromethyl methyl thioether in 20 ml of ethyl acetate were; then acided, and the mixture was refluxed for a fiirther 4 hours, with stirring. For working up, the cooled reaction mixture was washed twice using in each case 40 ml of water, dried over sodium sulphate and concentrated in vacuo, and the residue was purified by chromatography on silica gel (eluent:
dichloromethane).
This gave 1-methylthiorriethyl-4-bromo-6-trifluoromethyl-2-trifluoromethyl-benzimidazole of ine;lting point 56-60 C.

Le A 29 088 - 103 -214 86~2 Use Examdes:

In the Use Examples 4fich follow, the compounds listed below were employed as comparison substances:

ii ~ O-C -NH-C H3 ! (A) ~

O-(2-Isopropoxyphenyl) NI-methyl-carbamate (compare, for example, DE 1,108,202) I I
CHI~O-P=NH2 (B) I

O,S-Dimethyl-thiolo-phosphoramide (compare, for example, DE 1,210,835) LeA29088 -104-Example A

Ptaedon larvae test Solvent: 7 parts by weilot of dimethylfornnanide Emulsifier: 1 part by weiglit of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the ccmcentrate is diluted with water to the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of the active compowld of the desired concentration and are infested with mustard beetle larvae (Phaedon cochleariae), while the leaves are still moist.

After the specified period of time, the destruction in per cent is detemiined.
100%
means that all the beetle laniae have been killed; 0% means that none of the beetle larvae have been killed.

In this test, a superioir activity compared with the prior art is shown, for example, by the following corripounds of the Preparation Examples: 13, 14, 16, 18, 20, 22, 28, 29, 30, 56, 76, 80, 84, 85, 86, 89, 103 and 109.

Le A 29 088 - 105 -Table A

Phaedon Iarvae Test Active componnds Active compound Degree of de.s-concenhabion in % tniction in %
after 3 days 0 (A) 0.1 100 ao O-C -NH-CH3 0.01 70 0,001 0 -iCH, (known) F,C -N (85) 0.1 100 0_01 100 Cl -~N
0.001 100 CHz -OCHs ~-CF, --N

CH: -()CzHs F,C -N (86) 0,1 100 ~}--CF, 0.01 100 C1 ~N\ 0.001 100 LeA29088 - 106-2:t43612 Table A: ( ntinuati"

Phaedon Imvae Tesit Ac6ve compoimds Active compoimd Degree of des-concenhation in % huction in %
after 3 days F3C N(80) 0.1 100 Q-CF, 0,01 100 Br CH2--OC2HS 0,001 100 +
Br N
I ~>--CF3 ~C
/
3C N' F2C1~0 -. N (103) 0,1 100 --CF3 0.01 100 FzCO N
0.001 100 CHz-OCzHs F CO ~ -N (109) 0.1 100 Z I ~ \~----CF, 0.01 100 F2C~O / ~N
0,001 100 CH2 -O-CHz -C-CH

LeA29088 -107-Table A: (Conti.n=W

Phaedon Ia><vae Test Active compoiuids Active con>Ipound Degree of de.s-concentration in % tniction in %
after 3 days F,C .N (89) 0.1 100 >--CF, 0.01 100 Cl N\ 0.001 100 CHZ-O-n-qH7 >___<~F

3C N~
CH2-O-ri-C3H7 F,C N (90) 0.1 100 ,> -CF3 0.01 100 Cl N 0.001 100 CH=-O-CH2 -C=CH
+ =

C'H2-O-CHZ-C-CH
LeA2908~ - 108-Table A: (ContinuatiQu) Phaedon Larvae Test Active compotuxls Active conipowid Degtee of des-concenhation in % tniction in %
after 3 days F3C 11 (84) 0.1 100 ~ ~--=CF3 0.01 100 Br 14 \ 0.001 100 CH2-O-CH2-C=CH
+
sr rirr ~ ~~--CF, CH2-0-0l2-C=CH
F3C -N (56) 0.1 100 ~-CFs 0,01 100 Cl =N
0.001 100 CHZ-O-C:H(CH3)2 +
C .\ N
I >--'CF3 /
3C N\
CH2-O-C:H(CH3h I.eA29088 -109-~~~8 6 12 Table A: Gontinuat;iM) Phaedon I.arvae Test Active compouxb Active compound Degree of des-concentra6on in % huction in %
after 3 days F,C -N (76) 0 ,1 100 >--CF; 0.01 100 0.001 100 CH2-O-(--H(CH3)=
+
Br N
\
I >--CF, /
3C N\
CH2-0a:H(CH;~
Br (13) 0.1 100 \ 'N 0,01 100 ~ \>--CF, 0.001 100 /
F,C *N\
+ CH2-O-(:H(CHA
F3C .N
~}-CF3 N
Br CH2-O-CH(CH3)2 LeA29088 - 110-'Z1UM
Table A: (Continuati"n Phaedon Lvvae Tes't Active compounds Active compoiuid Degme of des-concentration in % hucfion in %
after 3 days Br (14) 0,1 100 ~= ~N\ 0.01 100 ~--CF' 0.001 100 ~ ~N

+ CH2-C)-n-C3H., F'C N

~ .. .
Br CH2-O=-n-C3H7 =' Br (16) 0.1 100 N\ 0.01 100 >--CFs 0.001 100 ~ :Iq~

Br (18) 0.1 100 ~~ 0.01 100 CF3 0.001 100 F3Ci CH2-O-CO-C(CH3)3 L.eA29Q88 -111-~~~~~12 1Ta1 e A-(Continuati,~,1 Phaedon Laivae Test Ac6ve compounds Aclive compound Degree of des-concenhation in % tntction in %
after 3 days Br (20) 0.1 100 ~ N 0.01 100 ~'F3 0.001 100 F3C N~
+ CHz-Q-CzHs F3C _-N
}--C:F3 --N
~ = Br CHZ-C--CHS .
Br (22) 0.1 '100 N 0.01 100 ~ '>-'CF, 0.001 100 ~
F,C N\

Br (28) 0.1 100 N 0.01 100 '>--CF, 0.001 100 F3C N ~~ zHs CHz-N
COC)C2H5 LeA29088 -112-Table A: (Contino?t Phaedon Lmvae Tesit Active compounds Active conipouuid Degree of de.s-concenhafion in % tniction in %
after 3 days Br (29) 0.1 100 \ ~N 0.01 100 ~ ~CF3 0,001 100 - N CH=-Nfi-C3Hl COOC2Hs Br (30) 0,1 100 -N 0,01 100 X>-CF 0.001 i00 ,N' FC
CHZ-N
COOCzHs L.eA29088 - 113-x le Plutella test Solvent: 7 parts by weigbt of dimethylformamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparal:ion of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and are infested with caterpillars of the diamond-back inoth (Plutella maculipennis) while the leaves are still moist.
After the specified period of time, the destruction in per cent is determined.
100%
means that all the caterpillai-s have been killed; 0% means that none of the caterpillars have been killed.

In this test, a superior activity compared with the prior art is shown, for example, by the following compounds af the Preparation Examples: 2, 3, 13, 14, 18, 20, 21, 28, 29, 30, 52, 56, 76, 80, 84, 85, 86, 103, 109 and 131.

LeA29088 - 114-~~.48612 Table R

Plutella Test Active compournls Active compo><nxi Degnee of des-concentration in % tnction in %
after 3 days O (A) 0.1 100 O-C-NH-CHj 0,01 100 0.001 10 CI-i-C3H7 (known) F,C -N~ (85) 0.1 100 CF3 0,01 100 C1 ~N
0,001 100 CH2 -OC=HS
+

~CF'3 3C I-N, CHz-OCZHS
F,C
\ ~-N~ (86) 0.1 100 CF, 0.01 100 'N 0.001 100 CH2-OC,HS

Le A 29 098 - 115 -~143 6 12 Table $= (C'ontinuati"n Plutella Test Active compowids Active con>Ipo ond Deglee of des-concenhaaion in % tcuction in %
after 3 days (84) 0.1 100 F'C 0.01 100 ~ --CF, 0.001 100 Br N
CH=-O-CFiZ-C=CH
+
Br N
:~C\
' ( /}~.CF 3 ,C N
CHz-O-C:H-C=CH:
F,C CCN N (80) 0,1 100 0,01 100 Br 0.001 100 CH2 -C-C:2HS
+
Br \ iN
~--C:F3 ~ ~N
3C \
CH,-OC,Hs F1C"O \ N (103) 0.1 100 I -CF, 0_01 100 FZ C~O /
]~N~
0.001 100 CHz --C1C2H5 Le A 29 088 - 116 -~14 8 6 12 Table B: (('Qn 'n 1 tup-u) Plutella Test Active compounds Active compound Degree of de.s-concentra6on in % tn><ction in %
after 3 days F C \ 'v\ (109) 0, i 100 2 I 0,0: 100 ~
F2C" 0 /
h\ 0.001 100 CHz-O~Hz-C=CH

CF3-0 \ ~,h (131) 0.1 100 1 ~~--CF, 0.01 10C
/
CF,-0 A 0.001 100 .CH2-O-CH2-C=CH
CI ::C J JJ~~~ (52) 0,1 100 ~ ~---CF, 0,01 lOC
CF, N' 0,001 100 -CN

F'C ,N~ (56) 0,1 100 , CF, 0,01 100 N
+ 0,001 100 CH2-O~'H(CH3)z N
C ~N\-CF3 3c CHz-O-CH(CH3h LeA29088 - 117-Table B: (Continuati9W

Plutella Test Active comipounds Active compoiuid Degnre of de.s-concenhation in % trnction in %
after 3 days (76) 0,1 100 0.01 lOC
Br / ,N.
CH2-O-CH(CH,j 0.001 100 +
Br N
~=--CF, jC N

CH2-0-C:H(CH3)_ Br " =
(2) 0.1 100 \ 0,01 100 ~ 0.001 100 CFs / N% CF
CHz-ItiT
CbOCIi, Br (3) . 0.1 100 ~ lv 0.01 loo 0,00 i 100 CF, 14% /=zHs LeA29088 - 118-Tahle B: (Continuati,m) Plutella Test Active compowxls Active compound Degree of des-concenhation in % tniction in %
after 3 days Br (13) 0.1 100 \ 0.01 100 I ~CF' 0.001 100 /
F,C~ -N
+ CH,-O4ZH(CH3n FjC
---CF

/ .N

Br CHz-0-CH(CHi)a Br (14) 0,1 100 \ N 0,01 1 CO
I \~F' 0.001 100 /

+ CH2-O-~1-CH;

C ~_CF' 'N
Br CHz-O-n-C3H;
Br (18) 0.1 100 N 0.01 100 I ,}-CF, 0.001 100 F3C N~
CHz -O-CO-C(CH3)3 TeA29088 -119-2148 6~2 Table B: (Continuatim) Plutella Test Active conipotuxk Active conipotmd Degtee of des-concenhation in % truction in %
after 3 days Br (20) 0,1 100 N 0.01 100 0.001 100 ~- N

+ CH3-O-CzHs F;C ~\ N
I ~ ~--CF3 N
Br CH; -O-CHS , Br (21) 0.1 100 ~ 0.01 100 I >--C:F, 0.001 100 ~
CF3 N% CH3 Br (28) 0.1 100 IIINCH N 0.01 100 ~--CF, 0.001 100 F3Cs COOCzHs LeA29088 - 120-~148 6 12 Table B: Continuati ~

Plutella Test Active compoimds Active compound Degtee of des-concentra6on in % huction in %
after 3 days Br (29) 0.1 100 0.01 100 F 0,001 100 CHz-N
COOC2H, Br (30) 0.1 100 N 0,01 100 I ~~~F3 0.001 100 N
FjC % ,i.CjHr COOC21=5 I,eA29088 - 121 -EAample C:

Heliothis viresceris Test Solvent: 7 parts by weight of dimethylformainide Emulsifier: 1 part by weight of allcylaryl polyglycol ether To produce a suitable preparatiion of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
Soya shoots (Glycine max) are treated by being dipped into the preparation of 115 active compound of the desired concentration and are infested with the tobacco budworm (Heliothis virescens) while the leaves are still moist.

After the specified period of tirne, the destruction in per cent is determined 100%
means that all the wonns have been killed; 0% means that none of the worms have been killed.

In this test, a superior activity compared with the prior art is shown, for example, by the following compounds of the Preparation Examples: 3, 13, 16, 18, 20, 52, 53, 56, 76, 80, 84, 85, 86, 89, 90, 103, 109 and 131.

Le A 29 088 - 122 -2~4 86 12 Table C:

Heliothis vi>rescens T'est Active compouncb Active con>Ipoumd Degree of des-concenhation in % ttuction in %
after 3 days O (A) 0.1 10 .1O-C-IVH-CH3 ~

( known ) F3C . N (85) 0.1 100 , ~ ~>---CF3 C1 ~

CI

:)c ~>---CF, ~ N
3C , CHz-OCzHs F,C N (86) 0.1 100 ~}--CF3 Cl ~ N

Le A 29 088 - 123 -Table C: Continuai:i r Heliothis virescens Test Active compounds Active compound Degme of des-concentration in % tniction in %
after 3 days F,C (84) 0.1 100 I ~ ~>--CF3 Br N \
CHi-O-CHz-C=CH
Br N
~>--CFs N
3C: ~
CHz-O-CH,-C=CH

(80) 0.1 100 FsC D-N ~
)--CF, I Br N\
C:H2 -OC, Hs Br N
~)--CF, :~:N
,C
C:Hz-OCzHs F C~ (103) 0.1 100 2I II ~CF3 FzC~O / N
CH2-OC2Hs LeA29088 - 124-Table C. (Continua&u) Heliothis virescens 'Test Active compounds Active compowid Degree of de.s-concentration in % ttuction in %
after 3 days F C"O (109) 0.1 100 2 1 ~> -CF;
F'C~O
CH=-0.CH2-C-CH
CF3-0 ~N (131) 0.1 100 ~ ~~---CF3 CFj-0 / N
CH2-O-CHz-C_CH
F,C N (89) 0.1 100 ~}-CF, "
C! N
C13x-Oi--C3H, -~-' ~/}_'CF, C'Hz-O-n-qH, Le A 29 088 - 125 -Table C: Continua.tQW

Heliothis vi>-cscens 'Test Active compoun& Active conltpoi,md Degicee of de.s-concentration in % tnilction in %
after 3 days F3C \ ~N (90) 0.1 10C
~ ; CF3 ---CH2-0=CH2-C=CH
+
_-N
~ ~>--CF3 ~~
~
CHz-C)-CHz-C=CH
Cl N (52) 0.1 100 ~~>--Cr3 CF, :::~:NN\ (5 3) 0.1 100 ~--CF, C1II ~ CH1-CN

LeA29088 - 126-Table C: ( ntinuatim) Heliothis vimcens ']Cest Active compom& Ac6ve conipouid Degme of de.s-concenttation in % huc6on in %
after 3 days F3C ~ N (56) 0.1 100 Cl N
\CH2-O-CH(CH,), +

CH, -O-CH(CH3)~
F3C N (76) 0.1 100 ~}-CF3 Br CHz-O-CH(CH3)2 +

Br ~~
~}--CF3 3C N\
CHz-O-CH(CH3h Br (3) 0.1 100 Le A 29 088 - 127 -Table C: (ContinuatiLQW

Heliottiis vinscens Test Active compounds Active compound Degiee of de.s-concentration in % tniction in %
after 3 days Bi (13) 0.1 100 N

+ CHõ-O-CH(CH,h Eh. CH; O CH(GH3}s Br (16) 0.1 100' N
>-CF, F,C
CHZ--O-CH=-C-CH
Br (18) 0.1 100 ~~-CF3 I:N N
F,C ~ \
CHZ--O-CO-C(CH,)3 LeA29088 - 128-_._.._ ~148 6) 12 Table C:(Contiinuati,~i Heliothis vi>->escens 'Cest Active compo>In>ds Active compound Degree of de.s-concentration in % truction in %
after 3 days F;r (20) 0.1 100 ~ CN I ~> -CF3 /
F,C N %
-F Cli,-O-(,HS
F3C \ N
I \>__CF3 / N

13r C1H,-0-CHs .

LeA29088 129-Exam. 1:

Tetranychus test (OP resistant) Solvent: 7 parts by weigbt of dimethylformamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water containing emulsifier to the desired concentration:c.

Bean plants (Phaseolus vulgaris) which are heavily infested with all development stages of the greenhouse red spider mite (Tetranychus urticae) are dipped into a preparation of active -;,ompound of the desired concentration.

After the specified period of time, the destruction in per cent is determined 100%
means that all the spicier mites have been killed; 0% means that none of the spider mites have been killed.
In this test, a superior activity compared with the prior art is shown, for example, by the following compounds of the Preparation Examples: 2, 3, 4, 16, 20, 83 and 84.

LeA29088 - 130-Table D:

Tehanychus Test (IJP resistant) Active conipounds Aefive conipound Degree of concenha6on in % dlestmiction in %
after 7 days O (B) 0.01 60 CH,O- i -NH2 0,001 0 (known) N (84) 0,01 100 0.001 95 F,C C"'CW%

Br CH2=~MH2-C=CH
+ =
Br N
~>--.CF', 3C N \
CH2--O-CH2-C=CH
Br (2) 0.01 100 :CN N 0.001 45 ~-- -CF3 CFl \ CH3 \COOCH;

LeA29088 - 131 -Table D: (Continuaticiu) Tehanychus Test (QP-resistant) Active compoun& Active compoumd Degree of o concenhation in % destfion in %
after 7 days Br (3) 0.01 100 N 0,001 60 >--CF3 CF3 N, C2Hs CH,-N
, (4) 0.01 100 Br 0,001 60 x5\>_CF3 CF/n-C,H7 \

Br (16) 0.01 100 N 0,001 60 >-CF, F,C N \
CH,--O-CHZ-C-CH
LeA29088 - 132-Table D: (Continuatior Tetianychus Test (C-P resistaint) Active conipounds Active compotmd Degme of concentration in % destnxhon in %
after 7 days Br (20) 0.01 98 N 0.001 80 ~}-CF, -- C:HZ-O-CHS

I >-CF3 Br CH2-O-CzHs CF3\ N (83) 0.01 100 ~~F3 0.001 80 Br / N
CH:2-O-n-qH1 Br N

CFs CHf2-O-n-CA
Le A 29 088 - 133 -xam le E:
Plutella Test Solvent: 31 patls by we:ight of acetone Emulsifier: 1 part by weigllt of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water containing emulsifier to the desired concentration.

Cabbage leaves (Brassica oleracea) are treated with the preparation of active compound of the des;ired concentration. A treated leaf is placed into a plastic dish and infested with larvae (L2) of the, diamond-back moth (Plutella xylostella).
After three days, in each case one iuntreated leaf is used to continue the *feeding of the larvae.

After the specified pc;riod of time, the destruction in per cent is determined. 100%
means that all the animals have been killed; 0% means that none of the animals have been killed.

In this test, a superior activit:y compared with the prior art is shown, for example, by the following conipound of the Preparation Examples: 87.

Le A 29 088 - 134 -Table E:

Plutella Test Active conipowxls Active compound Degree of de.s-concentration in % tniction in %
after 7 days O (A) 0.01 0 ii O-'i-CH, ( known ) CiN (87) 0.01 100 I ~ '}--CF3 ~~ N
CFy ,, Le A 29 088 - 135 -Example F
Ptraedon Test Solvent: 31 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water containing emulsifier to the desired concentration.

Cabbage leaves (Brassica oleracea) are treated with the preparation of active compound of the desired concentration. A treated leaf is placed into a plastic dish and infested with larvae (L2) of the mustard beetle (Phaedon cochleariae).
After three days, in each aLse one untreated leaf is used to continue the feeding of the larvae.

After the specified period of time, the destruction in per cent is determined.
100%
means that all the animals have been killed; 0% means that none of the animals have been killed.

In this test, a superior activity compared with the prior art is shown, for example, by the following compound of the Preparation Examples: 87.

Le A 29 088 - 136 -Table F:

Ptrac,~don Test Active compounds Active conipouuid Degme of de.s-concenhation in % tniction in %
after 7 days O (A) 0.01 0 n ~ ,O-C:-NH-CH3 O-i-CH, ( known. ) Cl ~ N (87) 0.01 100 I
' N
CF3 %

Le A 29 088 - 137 -Ex=le G:

Ctiitical concentration tesdnematodes Test nematode: Globodera rostochiensis Solvent: 31 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

The preparation of active compound is intimately mixed with soil which is heavily infested with the test nematodes. 'Ihe coricentration of the active compound in the preparation is of practically no importance here, only the amount of active compound per unit volume of soil, which is given in ppm (= mg/1), being decisive.
The treated soil is fiilled into pots, potatoes are planted therein, and the pots are kept at a greenhouse temperature of 20 C.
Affter six weeks, the potato roots are examined for cysts and the degree of effectiveness of the active compound is determined in %. The degree of effectiveness is 100% if infestation is avoided completely and 0% if the level of infestation is just as Hgh as in the control plants in untreated, but equally infested, soil.

In this test, a superioir activity compared with the prior art is shown, for example, by the following cornpound of the Preparation Examples: 13, 20 and 85.
LeA29088 - 138-Table G:

Nematode Test (Globodera mstochiensis) Active compoiux>s Degree of destn.iction in % at an active conipo><md concentration of 5ppm (A) 0 ii C\"
I
/
O--i-qH7 (known) CF3 N (85) 100 }-CF3 CI . N
, ~ .
CHZ-O-n-qH7 CI Cr~
~
~CFj /
CF3 M~
CHz -O'GiHs LeA29088 - 139-Table G: (ContinuatjQn) Nematode Test (Glabodera rostochiensis) Active conipounds Degree of de.stnic6on in % at an active compotuid concenhation of ppm Br (13) 100 -N
~ '}--CF3 CF3 ~N
CHr-O-~C3H;

-N
Br CHx- O-i-C3F~
Br (20) 100 CF3 ~

~}--CF;
--N
Br CHz- O-C2Hs LeA29088 - 140-Example H:

Psoivptes ovis Test Solvent: 35 parls by Nveight of ethylene glycol monomethyl ether Emulsifier: 35 pails by weight of nonylphenol polyglycol ether To produce a suitable preparation of active compound, 3 parts by weight of active compound are mixed with 7 parts of the solvent emulsified mixture indicated above, and the emulsion concentrate thus obtained is diluted with water to the desired concentration.

l ml of this preparation of active compound is pipetted into PP blister filntis of a .15 suitable~ size. Approximately 25 mites are then.transferred inlo the preparation of active compound.

After 24 hours, the a,.-tivity of the preparation of active compound is detetmined in %. 100% means that all mites have been killed, 0% means that no mites have been killed.

In this test, a superior activity compared with the prior art is shown, for example, by the following compounds of the Preparation Examples: 2, 3, 4, 6, 9, 10, 13, 14, 15, 16, 18, 19, 20, 43, 49, 51, 78 and 85.

Le A 29 088 - 141 -2~48 6~2 Table H

Psoropte.s ovis Test Active compounds Active compound Degree of des-concenhation in tiuction in %
ppm of a.i.

Br (2) 10 100 N
'~-CF, CF3 CH, ~ COOCH3 Br (3) .10 100 \ N

CF3 N~ ,CzHs CH2- N\COOCH, (4) 10 100 Br \ ~.
~~Fs CF3 /n-C3H7 CH2=N
\COOCH3 LeA29088 - 142-Table H (Continuatbn :

Psomptes ovis Test Active compowxls Active conipotmd Degree of des-concentration in tniction in %
ppm of a.i.

Br (6) 10 100 ~ N
I ~>----CF3 ~ h CF, \ ~O

C(CH,), Br (9) . 10 100 I ~}--C:F, CF, N
CH2-CH=CH-CH3 CF3 ~--C:F, Br CHZ-- CH~H-CH3 Le A 29 088 - 143 -1486 1~
Table H (Continuatim):

Psompkes ovis Test Active conipounds Active compoimd Degtee of des-concenhation in tniction in %
ppm of a.i.

Br (10) 10 100 CF3 N' /CH3 CH2'v~ACH=C\

Br (13) 10 100 \>CFs CF3 N \
CH2 --O-i-C3H, \>CF3 N
Br CHz-- O-i-C3H7 LeA29088 - 144-Table H (Continuati<)4:

Psoiopte.s ovis Test Active comiwtmds Active compouid Degiee of des-concenhation in tnxtion in %
ppm of ai.

Br (14) 10 100 r! 1 100 ( ~~--CF;
CF3 1,I
, CH2-O-n-C3H, +

'-"CF3 Br CHz-_ O-n-C3H, Br (15) 10 IOC

}--CF
\

('-H2-O{CH2)3-C6H5 +
Cr3 \>-CF3 N
CH1- O{CH2)3-C6H5 Br L,e A 29 088 - 145 -~148 6 1~
Table H (ContinuatiQn):

Psomptes ovis Test Active compomds Active conipoimd Degree of des-concentratiion in tntction in %
ppm of a.i.

Br (16) 10 100 ~ N 1 100 CFI
~ N
, \ CH2-0-CH2-C-CH

Br (18) 10 100 ~ ,N 1 100 I \CF3 / N
CF, 11 O

C(CH3)1 LeA29088 - 146-~148 6 12 Table H ContinuatiQo:

Psomptes ovis Test Active compounds Active conipoimd Degiee of des-concenhation in tnction in %
ppm of a.i.

Br (19) 10 100 I ~>--CF3 CI
CF3 \

+ -I ~}--CF3 Cl Br CH2--O-CH2 Br (20) 10 100 N
\\,----CF3 N
CF3 (:Hz-O-CzHs CF; 11 N
\)---CF3 B: (:Hz-O-CHS
Le A 29 088 - 147 -Table H (Continuati~ m):

Psoioptes ovis Test Active conipoumb Active compoimd Degree of de.s-concenhation in tniction in %
ppm of a.i.

,N (78) 10 100 \>---CF, CH=-O-CzH<

\>---CF3 '"N
CI-12-O-C2Hs F,C ~ (85) 10 .100 I \-CF3 /
CI N\
CH2-OCzHs CI
\-CF, C N
C N
3~

Le A 29 088 - 148 -~148 6 12 Table H Continuati~i :

Psoivptes ovis Test Active compounds Active compound Degme of de.s-concenhation in trucfion in %
ppm of ai.

Br (80) 10 100 I ~--CF, 1 100 CHz-0~H.
+

CF3 , L ~,-CF3 / N
Br C:Hz-O-CzH5 CF, ~ NN (43) 10 100 I ~~--CF3 Cl /
C1 \

LeA29088 - 149-Table H (Continuati"n:

Psoroptes ovis Test Active coropouids Active compound Degzee of des-concenhation in tiuction in %
ppm of a.i.

N (49) 10 10C
~~--CF, CF, CF, 0--N%
C1 + CH2 CL O,N
~>--CFa CFj CF3 CHZ
CF, ~N (51) 10 100 \> -CFz .

i~
+ C H2 C~, Cl~ C(CH3)3 ~~--CF3 CF3 ~h i0 CH2-C~
C(CH3;3 Le A 29 088 - 150 -E&=Ie I:

Peiiplanefa ametic=i Test:

Solvent: 35 pails by weight of ethylene glycol monomethyl ether Emulsifier: 35 parls by weight of nonylphenol polyglycol ether To produce a suitable preparation of active compound, 3 parts by weight of active compound are mixecl with 7 parts of the solvent emulsified mixture indicated above, and the emulsion concentrate thus obtained is diluted with water to the desired concentration,2 ml of this preparat:ion of active compound are pipetted onto filter paper discs (diameter: 9.5 cm) located in suitably sized Petri dishes. After the filter discs have dried, five cockroaches (Periplaneta americana) are transferred into the Petri dishes and covered.

After 3 days, the activity of the preparation of active compound is determined in %. 100% means that all cockroaches have been killed, 0% means that no cockroaches have been killel.

In this test, a superior activity compared with the prior art is shown, for example, by the following con-ipounds of the Preparation Examples: 3, 14, 16, 17, 18, 20, 22, 43, 53, 55, 56, 76, 79, 80, 83, 85, 87, 89, 90, 128, 129 and 131.

LeA29088 -151-T 1 I:

Periplaneta ameiicami Test Ac6ve compouxh Ac6ve conipotmd Degree of de.s-concentrafion in tiuction in %
ppm of a.i.

Br (3) 1000 100 ~ 100 100 ~ \}~F3 CF; / ~N ,CxHs CHZ-N
, Br (14) 1000 100 N
\\?--CF3 N
CF, + CIt-O-n-C3H7 CF3. N

Br CH2-Oi--qH7 LeA29088 - 152-Table I (Continuatian):

Periptanefa americmra Test Active compoimds Active compound Degme of de,s-concenhation in truction in %
ppm of ai.

Br (16) 1000 100 j ~-CF3 CF;
+ CHz-O-CHz-C=CH

>--CF, N
Br CH2-O-CH2-C-CH

B' (17) 1000 100 N
~~ Fs CFs N x O O _ u u CHs-O~-NH-C-NH ~ ~ 1 Br (18) 1000 100 -N
( ~>--CF, CFs 'N \ ~O

C(CH,)3 I.e A 29 088 - 153 -~.~48 6 12 Table I (Continuation):

Peziplaneta ametic.mra Test Active compotmds Active compound Degree of de.s-concenttation in truction in %
ppm of a.i.

Br (20) 1000 100 \ ~N 100 100 { F3 CF~ ~
+ CHZ-OL,H~
CF3~
c =;
Y~r Cjt.-o-C2H.
B_ Br (22) 1000 100 100 >50 LeA29088 - 154-Table I (Continuaticm):

Peiiplaneta americana Test Active compoimds Active compound Degree of des-concentration in tniction in %
ppm of a.i.

CF3 N (79) 1000 100 ~N>--CF3 100 100 ~ CH2 OH
~ N' I ~~--CF3 /
CF, N, CF, ~ N (43) 1000 100 I /
CH2CF~
C1 CN~

CF3 Cl'r-N' N (55)1000 100 ~Fs Cl \ i0 + CHI C
Cl ~\ N' C6Hs I ~-CF]
~
CF3~ N~ O
CH2-C,, C6H5 LeA29088 - 155-Table I Continuatiou):

Periptaneta anieticarra Test Ac6ve compourKb Ac6ve compoiuid Degme of des-concenha6on in tniction in %
ppm of a.i.

CI N (53) 1000 lOC
-~N~-CF3 CFj CH,-CN
CF,~~~N (56) 1000 100 11 \>--CF3 100 100 Cl + \CIt--C1-i-C3H, CI N
N
C"'Ll ~-C F3 CF3 \ CH2-O-i-C3H7 CF,. N (76) 1000 100 ~ ~>---CF, 100 100 Br + N C;Hz O-i-C3H, Br N
\">--CF;
CF, ~
(--H2-O-iZ3H, Le A 29 088 - 156 -Table I (Continuaticn):
Peliplaneta ameticmra Test Active compovnds Active compound Degree of cie.s-concenhation in truction in %
ppm of a.i.

F30 (128) 1000 100 ~}--CFs 100 >50 + CH, OC2H5 ~ N
~ / C~>-CF;
h F30 ~
CHz-OCZH5 CF3O ~ ~N (129) 1000 100 ( ~~--CF3 100 >50 CF3O/ ~' (:H2-O-C2HS
CF3O N (131) 1000 100 ~}---CF3 ~N
CFj CHZ-O-CH2-C=CH
LeA29088 -157-2.148 6 12 Table I (Continuati)n):

Peiipianeta americana Test Active compoiuids Active compoiuid Degree of des-concenha6on in truction in %
ppm of a.i.

CF3-1 ~ N ~ (85) 1000 100 \\>--CF3 100 100 + CHZ-OCzHs C C-- N~
I ~~-CF3 ~N
CF3 CH2-OCzHs CI (87) 1000 100 %-CF3 CHz-OC2Hs CF3 N (80) 1000 100 i ~---CF3 N
B
+ CHz-OC2Es Br -N \
\-CF3 N
CF, CHZ-OCzHs LeA29088 - 158-Table I (Continuatiot~:

Petiplaneta americana Test Active compourik Active conipoiuid Degree of des-concentration in tiuction in %
ppm of ai.

CF, a ,N (89) 1000 100 ~---CF3 Cl -N

+ CHZ-O-n-C,H, \
Ci IN
~}--CF;
CF3 ~N \
- CH2-O-n-C3H, CF3 O ~ -N (90) 1000 100 II ~--CF, 100 >50 C- 1' + CHz-O-CH,-C=CH
\
C N
~>---CF;

CHZ-O-CHz-C=CH
LeA29088 - 159-2.148612 Table I Continuatioa):

Peiiplanefa anieticana Test Active compounds Active conipoiuid Degree of des-concentration in tnwtion in %
ppm of a.i.

N (83) 1000 100 ',):
~~-CF3 Br + CH,-O-n-CH, Br ~ ~}---CF3 ''N
CF, \
CH.z-O-n-C., H, LeA29088 - 160-2,48612 Emmple =

iViusca domestica Tesit Solvent: 35 parts by weight of ethylene glycol monomethyl ether Emulsifier: 35 parts by weight of nonylphenol polyglycol ether To produce a suitable preparation of active compound, 3 parts by weight of active compound are mixed with 7 parts of the solvent emulsified mixture indicated above, and the emulsion coricentrate thus obtained is diluted with water to the desired concentration.

2 ml of this preparatiion of active compound are pipetted onto filter paper discs (diameter: 9.5 cm) loc:ated In suitably sized Petri dishes. After the filter discs have dried, 25 test animals (Musca domestica; strain WHO [N])) are transferred into the Petri dishes and covezed.

After 3 days, the activity of the preparation of active compound is determined in %.
100% means that all flies have been killed, 0% means that no flies have been killed In this test, a superior activity compared with the prior art is shown, for example, by the following compotnzds of the Preparation Examples: 16, 17, 18, 20, 56, 76, 80, 83, 87 and 89.

LeA29088 -161-___.

r11$~~2 Table J

1VLusca domestica Test Active compow& Active compoimd Degree of des-concenhation in tniction in %
ppm of a.i.

Br (16) 1000 100 + CH,--O-CH,-C=CH
C-; \ N -I / I \X-CF3 N
Br CHZ--O-CHZ-C-CH

Br (17) 1000 100 '}-_CF, 100 100 N O O
CF ~
~ CH; -O-C-tJH-C-Mi-(~ ~}- Cl Br (18) 1000 100 --N
~}--CF3 CHz-C~
C(CHO;
LeA29088 - 162-Table J: (Continuatioa) Musca domestica Tat Active compotzods Active compound Degree of des-concentration in tniction in %
ppin of ai.

Br (20) 1000 100 a CF;
+ CHz-O-C_HS
CFj'-, \ h ~ 3 Br CH2-O-C2F5 CF, a ~N1000 100 ~>--CF;
L- ---N
\
B + CH2-O-n-C3H, r \iN--CF, CF
a CHZ-O-n-CjH, I.e A 29 088 - 163 -1, 4 8 6 12 Table J: (Continuatic m) Musca doniestica Test Active compowKis Active compound Degiee of des-concentration in trix6on in %
ppm of a.i.

CF3 ~ N (89) 1000 100 ~ ~>---CFj + %
Cl CH2-O-n-C3H, --N

~ ---CFj CF; ~
CHZ-O-n-Cj H, Ci N (87) 1000 100 \>CFa N
CF3 CHz-OCZHS

CF,-, \ N (80) 1000 100 I CN\-CF3 ~
Br + CHZ-C-C2H5 Br CN\-CF3 CF3 N~
C:H2-OC,H5 LeA29088 - 164-Table J: (Continua.ticl) Musca domestica TL-st Active compowxis Active compound Degree of des-concenhation in tcuction in %
ppm of a.i.

Cr' N (56) 1000 100 ~ ~h}-CFs CI
+ CH2 O-i-C3H, C \
I L ~}--CF, CFj N\
CHZ-O-i.qH, CF, N (76) 1000 100 c ~>---CFj Br N
\
Br + CHz O-i-C3H, ~ ~~=--CF;
CF3 N\
CH2-O-i-C,H, Le A 29 088 - 165 -2 liL48 xam le K:

Phyt:ophthora Test (to:mato)/protective Solvent: 4.7 parts by weight of acetone Emulsifier: 0.3 part by weight of alkyl-aryl polyglycol ether To produce a suitable preparation of active compound, one part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

To test for protective activity, young plants are sprayed with the preparation of active compound until dripping wet. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Phytophthora infestans.
The plants are then placed in an incubation cabin at 20 C and about 100%
relative atmospheric humidity.

The test is evaluated 3 days after inoculation.
In this test, a clearly superior activity compared with the prior art is shown, for example, by the compound of Preparation Example 48.

LeA29088 - 166-~14 8 6 12 Table K:

Phytophthora Test (toimato)/pivtective Active compound Degcee of effectiveness in %of the unheated contml at an active con-poimd concentration of 10 ppm CF3 (48) 57 ~---CF3 + I
OCZHs CI :~N \CF3 p,j 0 CF3 õ

OCZHs LeA29088 - 167-Exam e L:

Plasmopaia Test (vir)es)/pivtective Solvent: 4.7 paits by weight of acetone Emulsifier: 0.3 pait by weight of allcyl-aryl polyglycol ether To produce a suitablle preparation of active compound, one part by weight of active compound is nzixed with the stated amounts of solvent and emulsifier, and the concentrate is dih.rted with water to the desired concentration.

To test for protective activity, young plants are sprayed with the preparation of active compound until dripping wet. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Plasmopara viticola and then remain in a humidity chamber at- 20 C to 22 C and 100% relative atmospheric humidity for one day. The plants are then placed in a greenhouse at 21 C and 90% atmospheric humidity for 5 days. The plants are then moistened and placed in a humidity chamber for one day.

The test is evaluated 6 days after the inoculation.

In this test, a clearly superior activity compared with the prior art is shown, for example, by the conipounds of the following Preparation Examples: 48, 53 and 130.

L.e A 29 088 - 168 -Table L:

Plasmopara Test (vines)/protective Active compound Degiee of effectiveness in % of the imtreated conttol at an active compound concenttation of10ppm Cl N (48) 60 1 c ~___cF

1=T O

+ CH2-P-OC:Hg CF3 \ /N OC=Hj \>CF3 Cl L-,N O
CHz-P-OCZHj OCzHs CF3 (53) 73 ~}--CF;
CI N
\

CF3O ~ N (130 74 \>CF, ) CF30' CH2-O-n-C3H7 LeA29088 - 169-xam le M:

Post-emergence Test Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, one part by weight of active compound is rn ixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

Test plants which have a height of 5 - 15 cm are sprayed with the preparation of active compound in such a way as to apply the particular amounts of active compound desired per unit area. After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control.

The figures denote:
0% = no action (like untreated control) 100% = total destruction In this test, a clearly superior activity compared with the prior art combined with a comparable crop plant selectivity is shown, for example, by the compound of Preparation Example 79.

LeA29088 - 170-Table M:

Post-emergence test (giEenhouse) Active compoiuid Application VNieat Alopacum Lolim Setana Anwurthus Galiutn pblygornnn Veronira Vlola rAe in g/ha CF3 N (79) 2000 10 95 99 100 100 95 100 100 100 ~-CF, Cl N
-' + CH2-OH
C N
+ ~--CF, ~

CHz-OH

Z\z }-.+
C>O
~-~
y.-..,.

Claims (11)

CLAIMS:
1. A benzimidazole of the general formula:

wherein:

R1 is hydrogen or C1-C8-alkyl;

R2 is CN, C1-C8-alkoxy or a substituted amino group, wherein the substitutent is selected from the group consisting of a C1-C8-alkyl and a carbo-C1-C4-alkoxy;

R3 is CF3;

X1, X2, X3 and X4, independently of each other, are hydrogen, halogen, C1-C6-halogenoalkyl, C1-C6-halogenoalkoxy, or X2 and X3 together form -O-CFC1-CFC1-O-, provided that X1, X2, X3 or X4 represents a C1-C6-halogenoalkyl group.
2. A benzimidazole according to claim 1, wherein:

R2 is C1-C8-alkoxy or a substituted amino group substituted by a C1-C8-alkyl group and a carbo-C1-C4-alkoxy.
3. A benzimidazole of the formula:
4. A pesticide composition for combating an animal parasite in the field of veterinary medicine, comprising at least one compound according to any one of claims 1 to 3, and an inert carrier.
5. An arthropodicidal or nematicidal composition comprising an arthropodicidally or nematicidally effective compound according to any one of claims 1 to 3, and an inert carrier.
6. Use of a compound according to any one of claims 1 to 3 for the preparation of a composition for combating an animal parasite in the field of veterinary medicine.
7. Use of a compound according to any one of claims 1 to 3 for the preparation of a composition for combating an anthropode or nematode.
8. A process for the preparation of a pesticide, comprising mixing a compound according to any one of claims 1 to 3 with an extender, a surface-active agent or a mixture thereof.
9. Use of a compound according to any one of claims 1 to 3 or a composition according to claim 4 for combating an animal parasite in the field of veterinary medicine.
10. Use of a compound according to any one of claims 1 to 3 or a composition according to claim 5 for combating an arthropode or nematode.
11. A process for the preparation of a compound according to claim 1 or 2, comprising:

reacting a compound of general formula (II):

wherein R3, X1, X2, X3 and X4 are as defined in claim 1, with a compound of the general formula (III):

wherein R1 is as defined in claim 1, R2 is as defined in claim 1 or 2, and A represents a leaving group.
CA002148612A 1992-11-06 1993-10-25 2-fluoroalkyl-substituted benzimidazoles, their preparation and their use as pesticides Expired - Fee Related CA2148612C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4237557A DE4237557A1 (en) 1992-11-06 1992-11-06 Substituted benzimidazoles
DEP4237557.6 1992-11-06
PCT/EP1993/002946 WO1994011349A1 (en) 1992-11-06 1993-10-25 2-fluoroalkyl-substituted benzimidazoles, their preparation and their use as pesticides

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