Benzimidazole derivatives

• US 6,080,776 A
• Filed: 01/11/1999
• Issued: 06/27/2000
• Est. Priority Date: 04/13/1995
• Status: Expired due to Fees

• Current Assignee: Bayer AG
• Original Assignee: Bayer AG
• Inventors: Stenzel, Klaus, Kugler, Martin, Marhold, Albrecht, Assmann, Lutz
• Primary Examiner(s): Morris, Patricia L.
• Application Number:
  US09/227,809
• Time in Patent Office: 533 Days
• Field of Search: 548/302.1, 548/304.7, 514/394
• US Class Current: 514/394
• CPC Class Codes: A01N 43/52 condensed with carbocyclic rings, e.g. benzimidazoles
• CPC Class Codes: A01N 43/80 five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
• CPC Class Codes: A01N 43/90 having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
• CPC Class Codes: A61P 25/22 Anxiolytics
• CPC Class Codes: C07D 403/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 409/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 413/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 491/04 Ortho-condensed systems

Abstract

Novel benzimidazole derivatives of the formula in which

R¹, R², X¹, X², X³, X⁴ and Y are each as defined in the description,

and acid addition salts and metal salt complexes thereof,

a process for preparing these compounds and their use as microbicides in crop protection and in the protection of materials.

Claims

1. A benzimidazole derivative of the formula (I) ##STR373## in which X¹, X², X³ and X⁴ independently of one another each represent hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, straight-chain or branched alkyl having 1 to 8 carbon atoms, straight-chain or branched halogenoalkyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, straight-chain or branched alkoxy having 1 to 8 carbon atoms, straight-chain or branched halogenoalkoxy having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, straight-chain or branched alkylthio having 1 to 8 carbon atoms, straight-chain or branched halogenoalkylthio having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, straight-chain or branched alkylsulphinyl having 1 to 8 carbon atoms, straight-chain or branched halogenoalkylsulphonyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, straight-chain or branched alkylsulphonyl having 1 to 8 carbon atoms, straight-chain or branched halogenoalkylsulphonyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, cycloalkyl having 3 to 6 carbon atoms which is optionally mono- to pentasubstituted by identical or different substituents from the group consisting of halogen and alkyl having 1 to 4 carbon atoms, represent hydroxycarbonyl, alkylcarbonyl having 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety, alkoxycarbonyl having 1 to 6 carbon atoms in the straight-chain or branched alkoxy moiety, cycloalkylcarbonyl having 3 to 6 carbon atoms in the cycloalkyl moiety or cycloalkoxycarbonyl having 3 to 6 carbon atoms in the cycloalkyl moiety, or

X² and X³ together also represent an alkylene chain having 3 or 4 members which is optionally mono- to hexasubstituted by halogen, alkyl having 1 to 4 carbon atoms and/or halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 halogen atoms and in which one or two (non-adjacent) carbon atoms may be replaced by oxygen atoms,

R¹ represents cyano or the groupings ##STR374## R⁶ represents straight-chain or branched alkyl having 1 to 4 carbon atoms, straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms or represents benzyl which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of halogen and halogenoalkyl having 1 to 2 carbon atoms and 1 to 5 identical or different halogen atoms,

R² represents a thienyl group, it being possible for this group to be mono- or disubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, hydroxyl, amino, formyl, carboxy, carbamoyl, thiocarbamoyl, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, alkoxycarbonyl having 1 to 6 carbon atoms in the alkoxy moiety, cycloalkyl having 3 to 6 carbon atoms, halogenoalkylsulphinyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkylsulphonyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, alkylamino having 1 to 4 carbon atoms, hydroxyalkylamino having 1 to 4 carbon atoms, dialkylamino having 1 to 4 carbon atoms in each alkyl group, alkylcarbonyl having 1 to 4 carbon atoms in the alkyl moiety, alkylcarbonylamino having 1 to 4 carbon atoms in the alkyl group, hydroxyiminoalkyl having 1 to 4 carbon atoms in the alkyl moiety, alkoximinoalkyl having 1 to 4 carbon atoms in the alkoxy moiety and having 1 to 4 carbon atoms in the alkyl moiety, alkylcarbonyloxy having 1 to 4 carbon atoms in the alkyl moiety and halogenoalkylcarbonyloxy having 1 to 4 carbon atoms in the halogenoalkyl group and 1 to 5 identical or different halogen atoms, and

Y represents a direct bond, represents CH₂ --CH₂, CO, SO₂, --CO--O-- or --SO--O--, where in the case of the last two groups the carbon atoms or the sulphur atom is linked to the nitrogen atom of the imidazole ring.

2. A benzimidazole derivative according to claim 1 which has the formula ##STR375##

3. A microbicidal composition comprising a microbicidally effective amount of at least one benzimidazole derivative according to claim 1 and an inert carrier.

4. A method for the control of undesired microorganisms, which method comprises applying to such microorganisms or to their habitat a microbicidally effective amount of at least one benzimidazole derivative according to claim 1.

5. A microbicidal composition comprising a microbicidally effective amount of the benzimidazole derivative according to claim 2 and an inert carrier.

6. A method for the control of undesired microorganisms, which method comprises applying to such microorganisms or to their habitat a microbicidally effective amount of the benzimidazole derivative according to claim 2.