TREA

NEW PYRIDINE CARBOXAMIDES

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Information

  • Patent Application
  • 20200354321
  • Publication Number
    20200354321
  • Date Filed
    January 29, 2019
    5 years ago
  • Date Published
    November 12, 2020
    3 years ago
Information
Abstract
The present invention relates to the use of compounds of formula I, wherein the variables are defined as given in the description and claims. The invention further relates to the compounds I and composition for compounds of formula I.
Description

The present invention relates to pyridine compounds and the N-oxides and the salts thereof for combating phytopathogenic fungi, and to the use and methods for combating phytopathogenic fungi and to seeds coated with at least one such compound. The invention also relates to processes for preparing these compounds, intermediates, processes for preparing such intermediates, and to compositions comprising at least one compound I.


In many cases, in particular at low application rates, the fungicidal activity of the known fungicidal compounds is unsatisfactory. Based on this, it was an object of the present invention to provide compounds having improved activity and/or a broader activity spectrum against phytopathogenic harmful fungi.


Surprisingly, this object is achieved by the use of the inventive pyridine compounds of formula I having favorable fungicidal activity against phytopathogenic fungi.


Accordingly, the present invention relates to use of the compounds of formula I




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wherein


wherein

  • X is O, S, NH
  • R1 is in each case independently selected from hydrogen, halogen, OH, CN, COOH, CONH2, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein
    • Rx is C1-C4-alkyl, C1-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted by 1, 2, 3, 4 or 5 substituents Rx1 independently selected from C1-C4-alkyl, halogen, OH, CN, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy;
    • wherein the acyclic moieties of R1 are unsubstituted or substituted with identical or different groups R1a which independently of one another are selected from:
  • R1a halogen, OH, CN, COOH, CONH2, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy, C1-C6-alkylthio, aryl and phenoxy, wherein the aryl group is unsubstituted or carries 1, 2, 3, 4 or 5 substituents R11a selected from the group consisting of halogen, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy;
    • wherein the carbocyclic, heteroaryl and aryl moieties of R1 are not further substituted or carry 1, 2, 3, 4, 5 or up to the maximum number of identical or different groups R1 which independently of one another are selected from:
    • R1b halogen, OH, CN, COOH, CONH2, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy and C1-C6-alkylthio;
  • R2 is in each case independently selected from halogen, OH, CN, COOH, CONH2, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C2-C4-alkenyl), N(C2-C4-alkenyl)2, NH(C2-C4-alkynyl), N(C2-C4-alkynyl)2, NH(C3-C6-cycloalkyl), N(C3-C6-cycloalkyl)2, N(C1-C4-alkyl)(C2-C4-alkenyl), N(C1-C4-alkyl)(C2-C4-alkynyl), N(C1-C4-alkyl)(C3-C6-cycloalkyl), N(C2-C4-alkenyl)(C2-C4-alkynyl), N(C2-C4-alkenyl)(C3-C6-cycloalkyl), N(C2-C4-alkynyl)(C3-C6-cycloalkyl), NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, S(O)n—C1-C6-alkyl, S(O)n-aryl, C1-C6-cycloalkylthio, S(O)n—C2-C6-alkenyl, S(O)n—C2-C6-alkynyl, CH(═O), C(═O)C1-C6-alkyl, C(═O)C2-C6-alkenyl, C(═O)C2-C6-alkynyl, C(═O)C3-C6-cycloalkyl, C(═O)NH(C1-C6-alkyl), CH(═S), C(═S)C1-C6-alkyl, C(═S)C2-C6-alkenyl, C(═S)C2-C6-alkynyl, C(═S)C3-C6-cycloalkyl, C(═S)O(C2-C6-alkenyl), C(═S)O(C2-C6-alkynyl), C(═S)O(C3-C7-cycloalkyl), C(═S)NH(C1-C6-alkyl), C(═S)NH(C2-C6-alkenyl), C(═S)NH(C2-C6-alkynyl), C(═S)NH(C3-C7-cycloalkyl),C(═S)N(C1-C6-alkyl)2, C(═S)N(C2-C6-alkenyl)2, C(═S)N(C2-C6-alkynyl)2, C(═S)N(C3-C7-cycloalkyl)2, C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, ORY, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; wherein
    • Rx is as defined above;
    • RY is C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, phenyl and phenyl-C1-C6-alkyl; wherein the phenyl groups are unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of CN, halogen, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy;
    • wherein the acyclic moieties of R2 are unsubstituted or substituted by groups R2a which independently of one another are selected from:
    • R2a halogen, OH, CN, COOH, CONH2, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy, C1-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or substituted by substituents R91a selected from the group consisting of halogen, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy;
    • wherein the carbocyclic, heteroaryl and aryl moieties of R2 are unsubstituted or substituted by groups R3b which independently of one another are selected from:
    • R2b halogen, OH, CN, COOH, CONH2, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy and C1-C6-alkylthio;
    • and wherein n is defined as above;
  • R3 is in each case independently selected from the substituents as defined for R2, wherein the possible substituents for R3 are R3a and R3b, respectively, which correspond to R2a and R2b, respectively;
  • R2, R3 together with the carbon atoms to which they are bound form a five-, six-, or seven-membered carbo-, heterocyclic or heteroaromatic ring; wherein the heterocyclic or heteroaromatic ring contains 1, 2, 3 or 4 heteroatoms selected from N, O and S, wherein N may carry one substituent RN selected from C1-C4-alkyl, C1-C4-halogenalkyl and SO2Ph, wherein Ph is unsubstituted or substituted by substituents selected from C1-C4-alkyl, halogen, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, and CN; and wherein S may be in the form of its oxide SO or SO2; and wherein in each case one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(═O) and C(═S); and wherein the carbo-, heterocyclic or heteroaromatic ring is substituent by (R23)m, wherein m is 0, 1, 2, 3 or 4;
  • R23 is in each case independently selected from halogen, OH, CN, COOH, CONH2, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C3-C6-cycloalkyl, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl and aryl; wherein the heterocycle and heteroaryl contains 1, 2 or 3 heteroatoms selected from N, O and S; and wherein in each case one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(═O) and C(═S); and wherein
    • Rx is as defined above;


wherein the acyclic moieties of R23 are unsubstituted or carry 1, 2, 3 or up to the maximum possible number of identical or different groups R23a which independently of one another are selected from:

    • R23a halogen, OH, CN, COOH, CONH2, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy, C1-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R91a selected from the group consisting of halogen, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, CN, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-alkylthio;


wherein the carbocyclic, heterocyclic, heteroaryl and aryl moieties of R23 are unsubstituted or substituted with identical or different groups R23b which independently of one another are selected from:

    • R23b halogen, OH, CN, COOH, CONH2, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy, and C1-C6-alkylthio;
  • R4 is in each case independently selected from hydrogen, halogen, OH, CN, COOH, CONH2, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein
    • Rx is as defined above
    • wherein the aliphatic moieties of R4 are unsubstituted or substituted with identical or different groups R2a which independently of one another are selected from:
    • R4a halogen, OH, CN, COOH, CONH2, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy, C1-C6-alkylthio, aryl and phenoxy, wherein the aryl group is unsubstituted or carries 1, 2, 3, 4 or 5 substituents R41a selected from the group consisting of halogen, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy;
    • wherein the cycloalkyl, heteroaryl and aryl moieties of R4 are not further substituted or carry 1, 2, 3, 4, 5 or up to the maximum number of identical or different groups R4b which independently of one another are selected from:
    • R4b halogen, OH, CN, COOH, CONH2, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy and C1-C6-alkylthio;
  • R5 is in each case independently selected from hydrogen, OH, CH(═O), C(═O)C1-C6-alkyl, C(═O)C2-C6-alkenyl, C(═O)C2-C6-alkynyl, C(═O)C3-C6-cycloalkyl, C1-C6-alkyl, C1-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, ORY, C2-C6-alkenyl, C2-C6-halogenalkenyl C2-C6-alkynyl, C2-C6-halogenalkynyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; wherein the aryl groups are unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of CN, halogen, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy;
    • RY is defined as above;
    • wherein the acyclic moieties of R5 are not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R5a which independently of one another are selected from:
    • R5a halogen, OH, CN, COOH, CONH2, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6-halogencycloalkyl, C3-C6-halogencycloalkenyl, C1-C4-halogenalkoxy, C1-C6-alkylthio, five- or six-membered heteroaryl, phenyl and phenoxy, wherein the heteroaryl, phenyl and phenoxy group is unsubstituted or carries one, two, three, four or five substituents R78a′ selected from the group consisting of halogen, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy;
      • wherein the alicyclic, phenyl, heterocyclic and heteroaryl moieties of R12 are not further substituted or carry one, two, three, four, five or up to the maximum number of identical or different groups R12b which independently of one another are selected from:
    • R5b halogen, OH, CN, COOH, CONH2, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy and C1-C6-alkylthio;
  • R6 is independently selected from hydrogen, halogen, OH, CN, COOH, CONH2, NO2, SH, C1-C6-alkylthio, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C1-C6-alkoxy, C1-C6-halogenalkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, aryloxy, heteroaryloxy, arylamino, heteroarylamino, arylthio, heteroarylthio, CH(═O), C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), C(═O)NH(C1-C6-alkyl), C(═O)N(C1-C6-alkyl)2, CR′═NOR″, a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, a five- or six-membered heteroaryl or aryl; wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(═O) and C(═S), and wherein the heterocycle and the heteroaryl contain independently one, two, three or four heteroatoms selected from N, O and S; and wherein R′ and R″ are independently selected from H, C1-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl or aryl; wherein the heterocycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S, and wherein R′ and R″ are independently unsubstituted or substituted by R′″ which is independently selected from halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C1-C6-alkoxy, C1-C6-halogenalkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and phenyl; or wherein the aliphatic moieties of and R6 are independently not further substituted or carry 1, 2, 3 or up to the maximum possible number of identical or different groups R6a, respectively, which independently of one another are selected from:
    • R6a halogen, OH, CN, COOH, CONH2, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH-aryl, N(aryl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkoxy, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy, C1-C6-alkylthio, C1-C6-halogenalkylthio, S(O)n—C1-C6-alkyl, S(O)n-aryl, CH(═O), C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), C(═O)NH(C1-C6-alkyl), C(═O)N(C1-C6-alkyl)2, CR′═NOR″, a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, aryl, phenoxy, a five-, six- or ten-membered heteroaryl; wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(═O) and C(═S), five- or six-membered heteroaryl and aryl; wherein the heterocycle and the heteroaryl contain independently 1, 2, 3 or 4 heteroatoms selected from N, O and S; wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(═O) and C(═S); wherein the carbocyclic, heterocyclic, aryl and phenyl groups are independently unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkylthio, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, and S(O)n—C1-C6-alkyl; and wherein Rx, R′, R″ and R″ are as defined above
    • wherein the carbocyclic, heterocyclic, heteroaryl and aryl moieties of R6 are independently not further substituted or carry 1, 2, 3, 4, 5 or up to the maximum number of identical or different groups R6b, respectively, which independently of one another are selected from:
    • R6b halogen, OH, CN, COOH, CONH2, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy, C1-C6-alkylthio, C1-C6-halogenalkylthio, S(O)n—C1-C6-alkyl, C1-C4-alkoxy-C1-C4-alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or substituted with substituents selected from the group consisting of halogen, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy;
    • and wherein Rx is as defined above; or
    • n is 0, 1, 2
  • R7 is independently selected from
    • halogen, OH, CN, COOH, CONH2, NO2, SH, C1-C6-alkylthio, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C1-C6-alkoxy, C1-C6-halogenalkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, aryloxy, heteroaryloxy, arylamino, heteroarylamino, arylthio, heteroarylthio, CH(═O), C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), C(═O)NH(C1-C6-alkyl), C(═O)N(C1-C6-alkyl)2, CR′═NOR″, a saturated or partially unsaturated three-, four, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, a five- or six-membered heteroaryl or aryl; wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(═O) and C(═S), and wherein the heterocycle and the heteroaryl contain independently one, two, three or four heteroatoms selected from N, O and S; and wherein R′ and R″ are independently selected from H, C1-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl or aryl; wherein the heterocycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S, and wherein R′ and R″ are independently unsubstituted or substituted by R′″ which is independently selected from halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C1-C6-alkoxy, C1-C6-halogenalkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and phenyl; or
    • wherein the aliphatic moieties of and R7 are independently not further substituted or carry 1, 2, 3 or up to the maximum possible number of identical or different groups R7a, respectively, which independently of one another are selected from:
    • R7a
    • halogen, OH, CN, COOH, CONH2, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH-aryl, N(aryl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkoxy, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy, C1-C6-alkylthio, C1-C6-halogenalkylthio, S(O)n—C1-C6-alkyl, S(O)n-aryl, CH(═O), C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), C(═O)NH(C1-C6-alkyl), C(═O)N(C1-C6-alkyl)2, CR′═NOR″, a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, aryl, phenoxy, a five-, six- or ten-membered heteroaryl; wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(═O) and C(═S), five- or six-membered heteroaryl and aryl; wherein the heterocycle and the heteroaryl contain independently 1, 2, 3 or 4 heteroatoms selected from N, O and S; wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(═O) and C(═S); wherein the carbocyclic, heterocyclic, aryl and phenyl groups are independently unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkylthio, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, and S(O)n—C1-C6-alkyl; and wherein Rx, R′, R″ and R″ are as defined above
    • wherein the carbocyclic, heterocyclic, heteroaryl and aryl moieties of R7 are independently not further substituted or carry 1, 2, 3, 4, 5 or up to the maximum number of identical or different groups R7b, respectively, which independently of one another are selected from:
    • R7b halogen, OH, CN, COOH, CONH2, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy, C1-C6-alkylthio, C1-C6-halogenalkylthio, S(O)n—C1-C6-alkyl, C1-C4-alkoxy-C1-C4-alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or substituted with substituents selected from the group consisting of halogen, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy;
    • and wherein Rx is as defined above;
    • n is 0, 1, 2
  • R8 is independently selected from CN, COOH, CONH2, C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, CH(═O), C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), C(═O)NH(C1-C6-alkyl), C(═O)N(C1-C6-alkyl)2, CR′═NOR″, a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, a five- or six-membered heteroaryl or aryl; wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(═O) and C(═S), and wherein the heterocycle and the heteroaryl contain independently one, two, three or four heteroatoms selected from N, O and S, and wherein heterocycle and heteroaryl are connected via C atom; and wherein R′ and R″ are independently selected from H, C1-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl or aryl; wherein the heterocycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S, and wherein R′ and R″ are independently unsubstituted or substituted by R′″ which is independently selected from halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C1-C6-alkoxy, C1-C6-halogenalkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and phenyl; or
    • wherein the aliphatic moieties of and R8 are independently not further substituted or carry 1, 2, 3 or up to the maximum possible number of identical or different groups R8a, respectively, which independently of one another are selected from:
    • R8a halogen, OH, CN, COOH, CONH2, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkoxy, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy, C1-C6-alkylthio, C1-C6-halogenalkylthio, S(O)n—C1-C6-alkyl, S(O)n-aryl, CH(═O), C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), C(═O)NH(C1-C6-alkyl), C(═O)N(C1-C6-alkyl)2, CR′═NOR″, a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, aryl, phenoxy, a five-, six- or ten-membered heteroaryl; wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(═O) and C(═S), five- or six-membered heteroaryl and aryl; wherein the heterocycle and the heteroaryl contain independently 1, 2, 3 or 4 heteroatoms selected from N, O and S; wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(═O) and C(═S); wherein the carbocyclic, heterocyclic, aryl and phenyl groups are independently unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkylthio, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, and S(O)n—C1-C6-alkyl; and wherein Rx, R′, R″ and R″ are as defined above
    • wherein the carbocyclic, heterocyclic, heteroaryl and aryl moieties of R8 are independently not further substituted or carry 1, 2, 3, 4, 5 or up to the maximum number of identical or different groups R8b, respectively, which independently of one another are selected from:
    • R8b halogen, OH, CN, COOH, CONH2, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy, C1-C6-alkylthio, C1-C6-halogenalkylthio, S(O)n—C1-C6-alkyl, C1-C4-alkoxy-C1-C4-alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or substituted with substituents selected from the group consisting of halogen, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy;
    • and wherein Rx is as defined above;
    • n is 0, 1, 2


and the N-oxides and the agriculturally acceptable salts thereof as fungicides.


The numbering of the ring members and substituents in the compounds of the present invention is as given in formula I above.


A skilled person will realize that compounds of formula I can be accessed via an amide coupling reaction of 3-aminopyridines of type II with carboxylic acids of type III. Among various reported methods for such amide coupling reactions, a robust method involves the treatment of carboxylic acids of type III with thionyl chloride or oxalyl chloride or dicyclohexylcarbodiimide in solvents like tetrahydrofurane, dimethylformamide or dichloromethane at room temperature. Subsequent addition of amines of type II in the presence of a base like triethylamine at room temperature gives the target compounds of type I (see: Chem. Soc. Rev. 2009, 606-631, or Tetrahedron 2005, 10827-10852).




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The compounds of the formula and III are commercial available.


The N-oxides may be prepared from the inventive compounds according to conventional oxidation methods, e. g. by treating compounds I with an organic peracid such as metachloroperbenzoic acid (cf. WO 03/64572 or J. Med. Chem. 38(11), 1892-903, 1995); or with inorganic oxidizing agents such as hydrogen peroxide (cf. J. Heterocyc. Chem. 18(7), 1305-8, 1981) or oxone (cf. J. Am. Chem. Soc. 123(25), 5962-5973, 2001). The oxidation may lead to pure mono-N-oxides or to a mixture of different N-oxides, which can be separated by conventional methods such as chromatography.


In the following, the intermediate compounds are further described. A skilled person will readily understand that the preferences for the substituents, also in particular the ones given in the tables below for the respective substituents, given herein in connection with compounds I apply for the intermediates accordingly. Thereby, the substituents in each case have independently of each other or more preferably in combination the meanings as defined herein.


If the synthesis yields mixtures of isomers, a separation is generally not necessarily required since in some cases the individual isomers can be interconverted during work-up for use or during application (e. g. under the action of light, acids or bases). Such conversions may also take place after use, e. g. in the treatment of plants in the treated plant, or in the harmful fungus to be controlled.


In the definitions of the variables given above, collective terms are used which are generally representative for the substituents in question. The term “Cn-Cm” indicates the number of carbon atoms possible in each case in the substituent or substituent moiety in question.


The term “halogen” refers to fluorine, chlorine, bromine and iodine.


The term “C1-C6-alkyl” refers to a straight-chained or branched saturated hydrocarbon group having 1 to 6 carbon atoms, e.g. methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl. Likewise, the term “C2-C4-alkyl” refers to a straight-chained or branched alkyl group having 2 to 4 carbon atoms, such as ethyl, propyl (n-propyl), 1-methylethyl (iso-propoyl), butyl, 1-methylpropyl (sec.-butyl), 2-methylpropyl (iso-butyl), 1,1-dimethylethyl (tert.-butyl).


The term “C1-C6-halogenalkyl” refers to an alkyl group having 1 or 6 carbon atoms as defined above, wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above. Examples are “C1-C2-halogenalkyl” groups such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl or pentafluoroethyl.


The term “C1-C6-hydroxyalkyl” refers to an alkyl group having 1 or 6 carbon atoms as defined above, wherein some or all of the hydrogen atoms in these groups may be replaced by OH groups.


The term “C1-C4-alkoxy-C1-C4-alkyl” refers to alkyl having 1 to 4 carbon atoms (as defined above), where According to one hydrogen atom of the alkyl radical is replaced by a C1-C4-alkoxy group (as defined above). Likewise, the term “C1-C6-alkoxy-C1-C4-alkyl” refers to alkyl having 1 to 4 carbon atoms (as defined above), where According to one hydrogen atom of the alkyl radical is replaced by a C1-C6-alkoxy group (as defined above).


The term “C2-C6-alkenyl” refers to a straight-chain or branched unsaturated hydrocarbon radical having 2 to 6 carbon atoms and a double bond in any position. Examples are “C2-C4-alkenyl” groups, such as ethenyl, 1-propenyl, 2-propenyl (allyl), 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl.


The term “C2-C6-alkynyl” refers to a straight-chain or branched unsaturated hydrocarbon radical having 2 to 6 carbon atoms and containing at least one triple bond. Examples are “C2-C4-alkynyl” groups, such as ethynyl, prop-1-ynyl, prop-2-ynyl (propargyl), but-1-ynyl, but-2-ynyl, but-3-ynyl, 1-methyl-prop-2-ynyl.


The term “C1-C6-alkoxy” refers to a straight-chain or branched alkyl group having 1 to 6 carbon atoms which is bonded via an oxygen, at any position in the alkyl group. Examples are “C1-C4-alkoxy” groups, such as methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methyl, propoxy, 2-methylpropoxy or 1,1-dimethylethoxy.


The term “C1-C6-halogenalkoxy” refers to a C1-C6-alkoxy radical as defined above, wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above. Examples are “C1-C4-halogenalkoxy” groups, such as OCH2F, OCHF2, OCF3, OCH2Cl, OCHCl2, OCCl3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chlorothoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC2F5, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoro¬propoxy, 2 chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3 bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2—C2F5, OCF2—C2F5, 1-fluoromethyl-2-fluoroethoxy, 1-chloromethyl-2-chloroethoxy, 1-bromomethyl-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy.


The term “C2-C6-alkenyloxy” refers to a straight-chain or branched alkenyl group having 2 to 6 carbon atoms which is bonded via an oxygen, at any position in the alkenyl group. Examples are “C2-C4-alkenyloxy” groups.


The term “C2-C6-alkynyloxy” refers to a straight-chain or branched alkynyl group having 2 to 6 carbon atoms which is bonded via an oxygen, at any position in the alkynyl group. Examples are “C2-C4-alkynyloxy” groups.


The term “C3-C6-cycloalkyl” refers to monocyclic saturated hydrocarbon radicals having 3 to 6 carbon ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl. Accordingly, a saturated three-, four-, five-, six-, seven-, eight-, nine or ten-membered carbocyclyl or carbocycle is a “C3-C10-cycloalkyl”.


The term “C3-C6-cycloalkenyl” refers to a monocyclic partially unsaturated 3-, 4- 5- or 6-membered carbocycle having 3 to 6 carbon ring members and at least one double bond, such as cyclopentenyl, cyclopentadienyl, cyclohexadienyl. Accordingly, a partially unsaturated three-, four, five-, six-, seven-, eight-, nine or ten-membered carbocyclyl or carbocycle is a “C3-C10-cycloalkenyl”.


The term “C3-C8-cycloalkyl-C1-C4-alkyl” refers to alkyl having 1 to 4 carbon atoms (as defined above), where According to one hydrogen atom of the alkyl radical is replaced by a cycloalkyl radical having 3 to 8 carbon atoms (as defined above).


The term “C1-C6-alkylthio” as used herein refers to straight-chain or branched alkyl groups having 1 to 6 carbon atoms (as defined above) bonded via a sulfur atom. Accordingly, the term “C1-C6-halogenalkylthio” as used herein refers to straight-chain or branched halogenalkyl group having 1 to 6 carbon atoms (as defined above) bonded through a sulfur atom, at any position in the halogenalkyl group.


The term “C(═O)—C1-C6-alkyl” refers to a radical which is attached through the carbon atom of the group C(═O) as indicated by the number valence of the carbon atom. The number of valence of carbon is 4, that of nitrogen is 3. Likewise the following terms are to be construed: NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C3-C6-cycloalkyl), N(C3-C6-cycloalkyl)2, C(═O)—NH(C1-C6-alkyl), C(═O)—N(C1-C6-alkyl)2.


The term “saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine or ten-membered heterocyclyl or heterocycle, wherein the heterocyclyl or heterocycle contains 1, 2, 3 or 4 heteroatoms selected from N, O and S” is to be understood as meaning both saturated and partially unsaturated heterocycles, wherein the ring member atoms of the heterocycle include besides carbon atoms 1, 2, 3 or 4 heteroatoms independently selected from the group of O, N and S. For example:


a 3- or 4-membered saturated heterocycle which contains 1 or 2 heteroatoms from the group consisting of O, N and S as ring members such as oxirane, aziridine, thiirane, oxetane, azetidine, thiethane, [1,2]dioxetane, [1,2]dithietane, [1,2]diazetidine; and a 5- or 6-membered saturated or partially unsaturated heterocycle which contains 1, 2 or 3 heteroatoms from the group consisting of O, N and S as ring members such as 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1,3,5-hexahydrotriazin-2-yl and 1,2,4-hexahydrotriazin-3-yl and also the corresponding -ylidene radicals; and


a 7-membered saturated or partially unsaturated heterocycle such as tetra- and hexahydroazepinyl, such as 2,3,4,5-tetrahydro[1H]azepin-1-,-2-,-3-,-4-,-5-,-6- or-7-yl, 3,4,5,6-tetrahydro[2H]azepin-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,4,7-tetrahydro[1H]azepin-1-,-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,6,7-tetrahydro[1H]azepin-1-,-2-,-3-,-4-,-5-,-6- or-7-yl, hexahydroazepin-1-,-2-,-3- or-4-yl, tetra- and hexahydrooxepinyl such as 2,3,4,5-tetrahydro[1H]oxepin-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,4,7-tetrahydro[1H]oxepin-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,6,7-tetrahydro[1H]oxepin-2-, -3-,-4-,-5-,-6- or-7-yl, hexahydroazepin-1-,-2-,-3- or-4-yl, tetra- and hexahydro-1,3-diazepinyl, tetra- and hexahydro-1,4-diazepinyl, tetra- and hexahydro-1,3-oxazepinyl, tetra- and hexahydro-1,4-oxazepinyl, tetra- and hexahydro-1,3-dioxepinyl, tetra- and hexahydro-1,4-dioxepinyl and the corresponding -ylidene radicals.


The term “substituted” refers to substitued with 1, 2, 3 or up to the maximum possible number of substituents.


The term “5-or 6-membered heteroaryl” or “5-or 6-membered heteroaromatic” refers to aromatic ring systems including besides carbon atoms, 1, 2, 3 or 4 heteroatoms independently selected from the group consisting of N, O and S, for example, a 5-membered heteroaryl such as pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,2,4-triazolyl-1-yl, 1,2,4-triazol-3-yl 1,2,4-triazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl and 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl; or a 6-membered heteroaryl, such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl and 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl.


Agriculturally acceptable salts of the inventive compounds encompass especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the fungicidal action of said compounds. Suitable cations are thus in particular the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, of the transition metals, preferably manganese, copper, zinc and iron, and also the ammonium ion which, if desired, may carry one to four C1-C4-alkyl substituents and/or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C1-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C1-C4-alkyl)sulfoxonium. Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogensulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C1-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting such inventive compound with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.


The inventive compounds can be present in atropisomers arising from restricted rotation about a single bond of asymmetric groups. They also form part of the subject matter of the present invention.


Depending on the substitution pattern, the compounds of formula I and their N-oxides may have one or more centers of chirality, in which case they are present as pure enantiomers or pure diastereomers or as enantiomer or diastereomer mixtures. Both, the pure enantiomers or diastereomers and their mixtures are subject matter of the present invention.


In the following, particular embodiments of the inventive compounds are described. Therein, specific meanings of the respective substituents are further detailed, wherein the meanings are in each case on their own but also in any combination with one another, particular embodiments of the present invention.


Furthermore, in respect of the variables, generally, the embodiments of the compounds I also apply to the intermediates.


R1 according to the invention is in each case independently selected from hydrogen, halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl;


wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; and


wherein


Rx is C1-C4-alkyl, C1-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted with one, two, three, four or five substituents Rx1 independently selected from C1-C4-alkyl, halogen, OH, CN, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy;


wherein the acyclic moieties of R1 are unsubstituted or substituted with identical or different groups R1a which independently of one another are selected from:


R1a halogen, OH, CN, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalky, C1-C4-halogenalkoxy, C1-C6-alkylthio, aryl and phenoxy, wherein the aryl and phenoxy group is unsubstituted or unsubstituted or substituted with R11a selected from the group consisting of halogen, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy;


wherein the carbocyclic, heteroaryl and aryl moieties of R1 are unsubstituted or substituted with identical or different groups R1b which independently of one another are selected from:


R1b halogen, OH, CN, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy and C1-C6-alkylthio.


For every R1 that is present in the inventive compounds, the following embodiments and preferences apply independently of the meaning of any other R1 that may be present in the ring.


According to one embodiment of formula I, R1 is H, halogen or C1-C6-alkyl, in particular H, CH3, Et, F, Cl, more specifically H, CH3, F or Cl most preferred H, F or Cl.


According to another embodiment of formula I, R1 is hydrogen.


According to still another embodiment of formula I, R1 is halogen, in particular Br, F or Cl, more specifically F or Cl.


According to another embodiment of formula I, R1 is F


According to another embodiment of formula I, R1 is Cl


According to another embodiment of formula I, R1 is Br.


According to still another embodiment of formula I, R1 is OH.


According to still another embodiment of formula I, R1 is COOH.


According to still another embodiment of formula I, R1 is CONH2.


According to still another embodiment of formula I, R1 is CN.


According to still another embodiment of formula I, R1 is NO2.


According to still another embodiment of formula I, R1 is SH.


According to still another embodiment of formula I R1 is NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2 or NH—SO2—Rx, wherein Rx is C1-C4-alkyl, C1-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted with one, two, three, four or five substituents Rx1 independently selected from C1-C4-alkyl, halogen, OH, CN, C1-C4-halogenalkyl, C1-C4-alkoxy, or C1-C4-halogenalkoxy. In particular C1-C4-alkyl, such as NHCH3 and N(CH3)2. In particular Rx is C1-C4-alkyl, and phenyl that is substituted with one CH3, more specifically SO2—Rx is CH3 and tosyl group (“Ts”).


According to still another embodiment of formula I, R1 is C1-C6-alkyl, in particular C1-C4-alkyl, such as CH3 or CH2CH3.


According to still another embodiment of formula I, R1 is C1-C6-halogenalkyl, in particular C1-C4-halogenalkyl, such as CF3, CHF2, CH2F, CCl3, CHCl2, CH2Cl, CF3CH2, CCl3CH2 or CF2CHF2.


According to still another embodiment of formula I, R1 is C2-C6-alkenyl or C2-C6-halogenalkenyl, in particular C2-C4-alkenyl or C2-C4-halogenalkenyl, such as CH═CH2, C(CH3)═CH2, CH═CCl2, CH═CF2, CCl═CCl2, CF═CF2, CH═CH2, CH2CH═CCl2, CH2CH═CF2, CH2CCl═CCl2, CH2CF═CF2, CCl2CH═CCl2, CF2CH═CF2, CCl2CCl═CCl2, or CF2CF═CF2.


According to still another embodiment of formula I, R1 is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as C≡CH, C≡CCl, C≡CF. CH2C≡CH, CH2C≡CCl, or CH2C≡CF.


According to still another embodiment of formula I, R1 is C1-C6-alkoxy, in particular C1-C4-alkoxy, more specifically C1-C2-alkoxy such as OCH3 or OCH2CH3.


According to still another embodiment of formula I, R1 is C1-C6-halogenalkoxy, in particular C1-C4-halogenalkoxy, more specifically C1-C2-halogenalkoxy such as OCF3, OCHF2, OCH2F, OCCl3, OCHCl2 or OCH2Cl, in particular OCF3, OCHF2, OCCl3 or OCHCl2.


According to still another embodiment of formula I R1 is C3-C6-cycloalkyl, in particular cyclopropyl.


According to still another embodiment of formula I, R1 is C3-C6-cycloalkyl, for example cyclopropyl, substituted with one, two, three or up to the maximum possible number of identical or different groups R1b as defined and preferably herein.


According to still another embodiment of formula I, R1 is C3-C6-halogencycloalkyl. In a special embodiment R1 is fully or partially halogenated cyclopropyl.


According to still another embodiment of formula I, R1 is unsubstituted aryl or aryl that is substituted with one, two, three or four Rb, as defined herein. In particular, R1 is unsubstituted phenyl or phenyl that is substituted with one, two, three or four Rb, as defined herein.


According to still another embodiment of formula, R1 is unsubstituted 5- or 6-membered heteroaryl. According to still a further embodiment, R1 is 5- or 6-membered heteroaryl that is substituted with one, two or three R1b, as defined herein.


According to still another embodiment of formula I, R1 is in each case independently selected from hydrogen, halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy and C3-C6-cycloalkyl; wherein the acyclic moieties of R1 are not further substituted or carry one, two, three, four or five identical or different groups R1a as defined below and wherein the carbocyclic, heteroaryl and aryl moieties of R1 are not further substituted or carry one, two, three, four or five identical or different groups R1b as defined below.


According to still another embodiment of formula I, R1 is independently selected from hydrogen, halogen, CN, OH, C1-C6-alkyl, C1-C6-alkoxy, C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, wherein the acyclic and cyclic moieties of R1 are unsubstituted or substituted by halogen.


According to still another embodiment of formula I, R1 is independently selected from hydrogen, halogen, CN, OH, C1-C6-alkyl, C1-C6-halogenalkyl, C1-C6-alkoxy and C1-C6-halogenalkoxy, in particular independently selected from H, F, Cl, Br, CN, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy.


According to still another embodiment of formula I, R1 is independently selected from H, CN, halogen or C1-C6-alkyl, in particular H, CN, CH3, Et, F, Cl, more specifically H, CN, CH3, F or Cl most preferred H, CH3, F or Cl.


R1a are the possible substituents for the acyclic moieties of R1.


R1a according to the invention is independently selected from halogen, OH, CN, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy, C1-C6-alkylthio, aryl and phenoxy, wherein the aryl group is unsubstituted or unsubstituted or substituted with R11a selected from the group consisting of halogen, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy, in particular selected from halogen, C1-C2-alkyl, C1-C2-halogenalkyl, C1-C2-alkoxy and C1-C2-halogenalkoxy, more specifically selected from halogen, such as F, Cl and Br.


In to one embodiment R1a is independently selected from halogen, OH, CN, C1-C2-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C2-halogenalkoxy. Specifically, R1a is independently selected from F, Cl, OH, CN, C1-C2-alkoxy, cyclopropyl, 1-F-cyclopropyl, 1-Cl-cyclopropyl, 1,1-F2-cyclopropyl, 1,1-Cl2-cyclopropyl and C1-C2-halogenalkoxy.


According to one embodiment R1a is independently selected from halogen, such as F, Cl, Br and I, more specifically F, Cl and Br.


According to still another embodiment of formula I, R1a is independently selected from OH, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C2-halogenalkoxy. Specifically, R1a is independently selected from OH, cyclopropyl and C1-C2-halogenalkoxy.


According to still another embodiment of formula I, R1a is independently selected from aryl and phenoxy, wherein the aryl group is unsubstituted or substituted with R11a selected from the group consisting of halogen, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy, in particular selected from halogen, C1-C2-alkyl, C1-C2-halogenalkyl, C1-C2-alkoxy and C1-C2-halogenalkoxy, more specifically selected from halogen, such as F, Cl and Br.


R1b are the possible substituents for the carbocyclic, heteroaryl and aryl moieties of R1.


R1b according to the invention is independently selected from halogen, OH, CN, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy and C1-C6-alkylthio;


According to one embodiment thereof R1 is independently selected from halogen, CN, C1-C2-alkyl, C1-C2-alkoxy, C1-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C2-halogenalkoxy. Specifically, R1b is independently selected from F, Cl, Br, OH, CN, CH3, OCH3, CHF2, OCHF2, cyclopropyl, 1-F-cyclopropyl, 1-Cl-cyclopropyl, 1,1-F2-cyclopropyl, 1,1-Cl2-cyclopropyl, OCF3, and OCHF2.


According to still another embodiment thereof R1b is independently selected from halogen, C1-C2-alkyl, C1-C2-alkoxy, C1-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C2-halogenalkoxy. Specifically, R1b is independently selected from halogen, CN, OH, CH3, CHF2, OCHF2, OCF3, OCH3, cyclopropyl, 1-F-cyclopropyl, 1-Cl-cyclopropyl, 1,1-F2-cyclopropyl, 1,1-Cl2-cyclopropyl and halogenmethoxy, more specifically independently selected from F, Cl, OH, CH3, OCH3, CHF2, OCH3, cyclopropyl, 1-F-cyclopropyl, 1-Cl-cyclopropyl, 1,1-F2-cyclopropyl, 1,1-Cl2-cyclopropyl, OCHF2 and OCF3.


Rx in the substituent NH—SO2—Rx is in each case independently selected from C1-C4-alkyl, C1-C4-halogenalkyl, unsubstituted aryl and aryl that is substituted with one, two, three, four or five substituents Rx1 independently selected from C1-C4-alkyl, halogen, OH, CN, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy. In particular, Rx is in each case independently selected from C1-C4-alkyl, halogen, OH, CN and phenyl that is substituted with one, two or three Rx1 independently selected from C1-C2-alkyl, more specifically Rx is in each case independently selected from C1-C4-alkyl and phenyl that is substituted with one CH3, more specifically SO2—Rx is the tosyl group (“Ts”).


Particularly preferred embodiments of R1 according to the invention are in Table P1 below, wherein each line of lines P1-1 to P1-16 corresponds to one particular embodiment of the invention. Thereby, for every R1 that is present in the inventive compounds, these specific embodiments and preferences apply independently of the meaning of any other R1 that may be present in the ring:












TABLE P1







No.
R1









P4-1
H



P4-2
Cl



P4-3
F



P4-4
Br



P4-5
OH



P4-6
ON



P4-7
NO2



P4-8
CH3



P4-9
CH2CH3



P4-10
CF3



P4-11
CHF2



P4-12
OCH3



P4-13
OCH2CH3



P4-14
OCF3



P4-15
OCHF2



P4-16
NH-Ts







“Ts” in the table stands for the tosylgroup SO2-(p-CH3)phenyl.






R2 is in each case independently selected from H, halogen, COOH, CONH2, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C2-C4-alkenyl), N(C2-C4-alkenyl)2, NH(C2-C4-alkynyl), N(C2-C4-alkynyl)2, NH(C3-C6-cycloalkyl), N(C3-C6-cycloalkyl)2, N(C2-C4-alkyl)(C2-C4-alkenyl), N(C2-C4-alkyl)(C2-C4-alkynyl), N(C2-C4-alkyl)(C3-C6-cycloalkyl), N(C2-C4-alkenyl)(C2-C4-alkynyl), N(C2-C4-alkenyl)(C3-C6-cycloalkyl), N(C2-C4-alkynyl)(C3-C6-cycloalkyl), NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, S(O)n—C1-C6-alkyl, S(O)n-aryl, C1-C6-cycloalkylthio, S(O)n—C2-C6-alkenyl, S(O)n—C2-C6-alkynyl, CH(═O), C(═O)C1-C6-alkyl, C(═O)C2-C6-alkenyl, C(═O)C2-C6-alkynyl, C(═O)C3-C6-cycloalkyl, C(═O)NH(C1-C6-alkyl), CH(═S), C(═S)C1-C6-alkyl, C(═S)C2-C6-alkenyl, C(═S)C2-C6-alkynyl, C(═S)C3-C6-cycloalkyl, (═S)O(C2-C6-alkenyl), C(═S)O(C2-C6-alkynyl), C(═S)O(C3-C7-cycloalkyl), C(═S)NH(C1-C6-alkyl), C(═S)NH(C2-C6-alkenyl), C(═S)NH(C2-C6-alkynyl), C(═S)NH(C3-C7-cycloalkyl),C(═S)N(C1-C6-alkyl)2, C(═S)N(C2-C6-alkenyl)2, C(═S)N(C2-C6-alkynyl)2, C(═S)N(C3-C7-cycloalkyl)2, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, ORY, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; wherein

    • Rx is as defined above;
    • RY is C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl; phenyl and phenyl-C1-C6-alkyl; wherein the phenyl group is unsubstituted or substituted with substituents selected from the group consisting of halogen, CN, OH, C1-C6-alkyl, C1-C6-halogenalkyl, C1-C6-alkoxy and C1-C6-halogenalkoxy;
    • wherein the acyclic moieties of R2 are unsubstituted or substituted with groups R2a which independently of one another are selected from:
    • R2a halogen, OH, CN, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy, C1-C6-alkylthio, aryl and phenoxy, wherein the aryl and phenoxy group is unsubstituted or substituted with substituents R21a selected from the group consisting of halogen, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy;
    • wherein the carbocycle, heteroaryl and aryl moieties of R2 are unsubstituted or substituted with groups R2b which independently of one another are selected from:
    • R2b halogen, OH, CN, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy and C1-C6-alkylthio.


According to one embodiment of formula I, R2 is selected from the group consisting of halogen, CN, C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C1-C6-alkoxy, C1-C6-halogenalkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, and ORY.


According to still another embodiment of formula I, R2 is halogen, in particular F, Cl, Br or I, more specifically F, Cl or Br, in particular F or Cl.


According to still another embodiment of formula I, R2 is F.


According to still another embodiment of formula I, R2 is Cl.


According to still another embodiment of formula I, R2 is Br.


According to still another embodiment of formula I, R2 is COOH.


According to still another embodiment of formula I, R2 is CONH2.


According to still another embodiment of formula I, R2 is OH.


According to still another embodiment of formula I, R2 is CN.


According to still another embodiment of formula I, R2 is NO2.


According to still another embodiment of formula I, R2 is SH.


According to still another embodiment of formula I, R2 is NH2.


According to still another embodiment of formula I, R2 is, NH(C1-C4-alkyl), in particular NH(CH3), NH(C2H5).


According to still another embodiment of formula I, R2 is, N(C1-C4-alkyl)2, in particular NH(CH3)2, NH(C2H5)2.


According to still another embodiment of formula I, R2 is, NH(C2-C4-alkenyl), in particular NH(CH═CH2), NH(CH2CH═CH2).


According to still another embodiment of formula I, R2 is N(C2-C4-alkenyl)2, in particular N(CH═CH2)2, N(CH2CH═CH2)2.


According to still another embodiment of formula I, R2 is, NH(C2-C4-alkynyl), in particular NH(C≡CH), NH(CH2C≡CH).


According to still another embodiment of formula I, R2 is, N(C2-C4-alkynyl)2, in particular N(C≡CH)2, N(CH2C≡CH)2.


According to still another embodiment of formula I, R2 is, NH(C3-C6-cycloalkyl), in particular NH(C3H7), NH(C4H2).


According to still another embodiment of formula I, R2 is N(C3-C6-cycloalkyl)2, in particular N(C3H7)2, N(C4H2)2.


According to still another embodiment of formula I, R2 is N(C1-C4-alkyl)(C2-C4-alkenyl), in particular N(CH3)(CH═CH2), N(CH3)(CH2CH═CH2), N(C2H5)(CH═CH2), N(C2H5)(CH2CH═CH2).


According to still another embodiment of formula I, R2 is N(C1-C4-alkyl)(C2-C4-alkynyl), in particular N(CH3)(C≡CH), N(CH3)(CH2C≡CH), N(C2H5)(C≡CH), N(C2H5)(CH2C≡CH).


According to still another embodiment of formula I, R2 is N(C1-C4-alkyl)(C3-C6-cycloalkyl), in particular N(CH3)(C3H7), N(CH3)(C4H2), N(C2H5)(C3H7), N(CH3)(C4H2).


According to still another embodiment of formula I, R2 is N(C2-C4-alkenyl)(C2-C4-alkynyl), in particular N(CH═CH2)(C≡CH), N(CH2CH═CH2)(CH2C≡CH), N(CH═CH2)(C≡CH), N(CH2CH═CH2)(CH2C≡CH).


According to still another embodiment of formula I, R2 is N(C2-C4-alkenyl)(C3-C6-cycloalkyl), in particular N(CH═CH2)(C3H7), N(CH2CH═CH2)(C4H2), N(CH═CH2)(C3H7), N(CH2CH═CH2)(C4H2).


According to still another embodiment of formula I, R2 is N(C2-C4-alkynyl)(C3-C6-cycloalkyl), in particular N(C≡CH)(C3H7), N(CH2C≡CH)(C4H2), N(C≡CH)(C3H7), N(CH2C≡CH)(C4H2).


According to still another embodiment of formula I, R2 is, NH(C(═O)(C1-C4-alkyl), in particular NH(C(═O)(CH3), NH(C(═O)(C2H5).


According to still another embodiment of formula I, R2 is N(C(═O)(C1-C4-alkyl)2, in particular N(C(═O)(CH3)2, N(C(═O)(C2H5)2.


According to a further specific embodiment of formula I, R2 is NH—SO2—Rx such as NH—SO2—CH3, NH—SO2—CH2—CH3, NH—SO2—CF3, NH—SO2-Ts.


According to still another embodiment of formula I, R2 is S(O)n—C1-C6-alkyl such as SCH3, S(═O) CH3, S(O)2CH3.


According to still another embodiment of formula I, R2 is S(O)n-aryl such as S-phenyl, S(═O) phenyl, S(O)2phenyl.


According to still another embodiment of formula I, R2 is S(O)n—C2-C6-alkenyl such as SCH═CH2, S(═O)CH═CH2, S(O)2CH═CH2, SCH2CH═CH2, S(═O)CH2CH═CH2, S(O)2CH2CH═CH2.


According to still another embodiment of formula I, R2 is S(O)n—C2-C6-alkynyl such as SC≡CH, S(═O)C≡CH, S(O)2C≡CH, SCH2C≡CH, S(═O)CH2C≡CH, S(O)2CH2C≡CH.


According to a further specific embodiment of formula I, R2 is CH(═O).


According to a further specific embodiment of formula I, R2 is C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl) or C(═O)NH(C1-C6-alkyl), wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.


According to a further specific embodiment of formula I, R2 is C(═O)C2-C6-alkenyl, C(═O)O(C2-C6-alkenyl) or (═O)NH(C2-C6-alkenyl) wherein alkenyl is CH═CH2, CH2CH═CH2.


According to a further specific embodiment of formula I, R2 is C(═O)C2-C6-alkynyl, C(═O)O(C2-C6-alkynyl) or C(═O)NH(C2-C6-alkynyl), wherein alkynyl is C≡CH, CH2C≡CH.


According to a further specific embodiment of formula I, R2 is C(═O)C3-C6-cycloalkyl, C(═O)O(C3-C6-cycloalkyl) or C(═O)NH(C3-C6-cycloalkyl), wherein cycloalkyl is cyclopropyl (C3H7) or cyclobutyl (C4H2).


According to a further specific embodiment of formula I, R2 is CH(═S).


According to a further specific embodiment of formula I, R2 is C(═S)C1-C6-alkyl, C(═S)OC1-C6-alkyl, C(═S)NH(C1-C6-alkyl) or C(═S)NH(C1-C6-alkyl), wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.


According to a further specific embodiment of formula I, R2 is C(═S)C2-C6-alkenyl, C(═S)OC2-C6-alkenyl, C(═S)NH(C2-C6-alkenyl) or C(═S)N(C2-C6-alkenyl)2, wherein alkenyl is CH═CH2, CH2CH═CH2.


According to a further specific embodiment of formula I, R2 is C(═S)C2-C6-alkynyl, C(═S)O(C2-C6-alkynyl), C(═S)NH(C2-C6-alkynyl) or C(═S)N(C2-C6-alkynyl)2, wherein alkynyl is C≡CH, CH2C≡CH.


According to a further specific embodiment of formula I, R2 is C(═S)C3-C6-cycloalkyl, C(═S)O(C3-C7-cycloalkyl), C(═S)NH(C3-C7-cycloalkyl) or, C(═S)N(C3-C7-cycloalkyl)2, wherein cycloalkyl is cyclopropyl (C3H7) or cyclobutyl (C4H2).


According to still another embodiment of formula I, R2 is C1-C6-alkyl, in particular C1-C4-alkyl, such as CH3. or C2H5, in particular CH3 or CH2CH3.


According to still another embodiment of formula I, R2 is C1-C6-halogenalkyl, in particular C1-C4-halogenalkyl, such as CF3, CCl3, FCH2, ClCH2, F2CH, Cl2CH, CF3CH2, CCl3CH2 or CF2CHF2. According to still a further embodiment of formula I, R2 is C2-C6-alkenyl, in particular C2-C4-alkenyl, such as CH═CH2, C(CH3)═CH2, CH2CH═CH2.


According to a further specific embodiment of formula I, R2 is C2-C6-halogenalkenyl, in particular C2-C4-halogenalkenyl, more specifically C2-C3-halogenalkenyl such as CH═CHF, CH═CHCl, CH═CF2, CH═CCl2, CH2CH═CHF, CH2CH═CHCl, CH2CH═CF2, CH2CH═CCl2, CF2CH═CF2, CCl2CH═CCl2, CF2CF═CF2, CCl2CCl═CCl2.


According to still a further embodiment of formula I, R2 is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as C≡CH, CH2C≡CH, C≡CCl, CH2C≡CCl, or CCl2C≡CCl.


According to a further specific embodiment of formula I, R2 is ORY, wherein RY is C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl.


According to a further specific embodiment of formula I, R2 is ORY, wherein RY is C1-C6-alkyl, in particular C1-C4-alkyl, more specifically C1-C2-alkoxy. R2 is such as OCH3 or OCH2CH3.


According to a further specific embodiment of formula I, R2 is ORY, wherein RY is C1-C6-halogenalkyl, in particular C1-C4-halogenalkyl, more specifically C1-C2-halogenalkyl. R2 is such as OCF3, OCHF2, OCH2F, OCCl3, OCHCl2 or OCH2Cl, in particular OCF3, OCHF2, OCCl3 or OCHCl2.


According to a further specific embodiment of formula I, R2 is ORY, wherein RY C2-C6-alkenyl, in particular C2-C4-alkenyl, more specifically C1-C2-alkenyl. R2 is such as OCH═CH2, OCH2CH═CH2.


According to a further specific embodiment of formula I, R2 is ORY, wherein RY C2-C6-halogenalkenyl, in particular C2-C4-halogenalkenyl, more specifically C1-C2-halogenalkenyl.


According to a further specific embodiment of formula I, R2 is ORY, wherein RY C2-C6-alkynyl, in particular C2-C6-alkynyl, in particular C2-C4-alkynyl, more specifically C1-C2-alkynyl. R2 is such as OC≡CH,


According to a further specific embodiment of formula I, R2 is ORY, wherein RY C2-C6-halogenalkynyl, in particular C2-C6-halogenalkynyl, in particular C2-C4-halogenalkynyl, more specifically C1-C2-halogenalkynyl. R2 is such as OC≡CCl, OCH2C≡CCl, or OCCl2C≡CCl.


According to still another embodiment of formula I, R2 is is ORY, wherein RY C3-C6-cycloalkenyl, in particular cyclopropenyl.


According to still another embodiment of formula I, R2 is C3-C6-cycloalkyl, in particular cyclopropyl.


According to still another embodiment of formula I, R2 is C3-C6-halogencycloalkyl. In a special embodiment R2b is fully or partially halogenated cyclopropyl, such as 1-F-cyclopropyl, 1-Cl-cyclopropyl, 1,1-F2-cyclopropyl, 1,1-Cl2-cyclopropyl.


According to still another embodiment of formula I, R2 is phenyl-C1-C6-alkyl, such as phenyl-CH2, wherein the phenyl moiety in each case is unsubstituted or substituted by one, two or three identical or different groups R2b which independently of one another are selected from halogen, C1-C2-alkyl, C1-C2-alkoxy, C1-C2-halogenalkyl and C1-C2-halogenalkoxy, in particular F, Cl, Br, CH3, OCH3, CF3 and OCF3.


According to still another embodiment of formula I, R2 is aryl, in particular phenyl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted with identical or different groups R2b which independently of one another are selected from CN, halogen, C1-C2-alkyl, C1-C2-alkoxy, C1-C2-halogenalkyl and C1-C2-halogenalkoxy, in particular CN, F, Cl, Br, CH3, OCH3, CHF2, OCHF2, CF3 and OCF3. According to one embodiment, R2 is unsubstituted phenyl. According to another embodiment, R2 is phenyl, that is substituted with one, two or three, in particular one, halogen, in particular selected from F, Cl and Br, more specifically selected from F and Cl.


According to still another embodiment of formula I, R2 is a 5-membered heteroaryl such as pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,2,4-triazolyl-1-yl, 1,2,4-triazol-3-yl 1,2,4-triazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl and 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl.


According to still another embodiment of formula I, R2 is a 6-membered heteroaryl such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl and 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl.


According to still another embodiment of formula I, R2 is in each case independently selected from halogen, CN, C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1-C6-halogenalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl and C3-C6-halogencycloalkyl, wherein the acyclic moieties of R2 are unsubstituted or substituted with identical or different groups R2a as defined and preferably defined herein, and wherein the carbocyclic, phenyl and heteroaryl moieties of R2 are unsubstituted or substituted with identical or different groups R2b as defined and preferably defined herein.


According to still another embodiment of formula I, R2 is in each case independently selected from halogen, CN, C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1-C6-halogenalkoxy; wherein the acyclic moieties of R2 are unsubstituted or substituted with identical or different groups R2a as defined and preferably defined herein.


According to still another embodiment of formula I, R2 is in each case independently selected from CN, halogen, C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkynyl, ORY, C3-C6-cycloalkyl; wherein RY is C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl or C2-C6-alkynyl.


R2a are the possible substituents for the acyclic moieties of R2.


According to one embodiment R2a is independently selected from halogen, OH, CN, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy, C1-C6-alkylthio, aryl and phenoxy, wherein the aryl and phenyl group is unsubstituted or substituted with substituents R21a selected from the group consisting of halogen, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy.


According to one embodiment R2a is independently selected from halogen, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C4-halogenalkoxy. Specifically, R2a is independently selected from F, Cl, Br, I, C1-C2-alkoxy, cyclopropyl, 1-F-cyclopropyl, 1-Cl-cyclopropyl, 1,1-F2-cyclopropyl, 1,1-Cl2-cyclopropyl and C1-C2-halogenalkoxy.


According to still another embodiment of formula I, R2a is independently halogen, in particular selected from F, Cl, Br and I, more specifically F, Cl and Br.


R2b are the possible substituents for the carbocyclic, heteroaryl and phenyl moieties of R2. R2b according to the invention is independently selected from halogen, OH, CN, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy and C1-C6-alkylthio.


According to one embodiment thereof R2b is independently selected from halogen, CN, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl and C1-C4-halogenalkoxy, in particular halogen, C1-C4-alkyl and C1-C4-alkoxy. Specifically, R2b is independently selected from F, Cl, CN, CH3, OCH3 and halogenmethoxy.


Particularly preferred embodiments of R2 according to the invention are in Table P2 below, wherein each line of lines P2-1 to P2-41 corresponds to one particular embodiment of the invention, wherein P2-1 to P2-41 are also in any combination with one another a preferred embodiment of the present invention. The connection point to the carbon atom, to which R2 is bound is marked with “#” in the drawings.












TABLE P2







No.
R2









P2-1
CH3



P2-2
CH2F



P2-3
CHF2



P2-4
CF3



P2-5
C2H5



P2-6
CH(CH3)2



P2-7
CH2CH2CH3



P2-8
CH2CH2CH2CH3



P2-9
CH2CH(CH3)2



P2-10
C(CH3)3



P2-11
CH2CH2CH2CH2CH3



P2-12
CH═CH2



P2-13
CH2CH═CH2



P2-14
C≡CH



P2-15
CH2C≡CH



P2-16
CH2CH2CH(CH3)2



P2-17
OH



P2-18
OCH3



P2-19
OCHF2



P2-20
OC2H5



P2-21
CN



P2-22
F



P2-23
Cl



P2-24
Br



P2-25
NO2



P2-26
NH2



P2-27
CO—NH2



P2-28
CO—NH(CH3)



P2-29
HNCH3



P2-30
HNC2H5



P2-31
(CH3)2N



P2-32
SO2H



P2-33
SO2—CH3



P2-34
SO—CH3



P2-35
S—CH3







P2-36


embedded image









P2-37


embedded image









P2-38


embedded image









P2-39


embedded image









P2-40


embedded image









P2-41


embedded image












R3 is in each case independently selected from halogen, OH, COOH, CONH2, CN, NO2,SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C2-C4-alkenyl), N(C2-C4-alkenyl)2, NH(C2-C4-alkynyl), N(C2-C4-alkynyl)2, NH(C3-C6-cycloalkyl), N(C3-C6-cycloalkyl)2, N(C2-C4-alkyl)(C2-C4-alkenyl), N(C2-C4-alkyl)(C2-C4-alkynyl), N(C2-C4-alkyl)(C3-C6-cycloalkyl), N(C2-C4-alkenyl)(C2-C4-alkynyl), N(C2-C4-alkenyl)(C3-C6-cycloalkyl), N(C2-C4-alkynyl)(C3-C6-cycloalkyl), NH((═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, S(O)n—C1-C6-alkyl, S(O)n-aryl, C1-C6-cycloalkylthio, S(O)n—C2-C6-alkenyl, S(O)n—C2-C6-alkynyl, CH(═O), C(═O)C1-C6-alkyl, C(═O)C2-C6-alkenyl, C(═O)C2-C6-alkynyl, C(═O)C3-C6-cycloalkyl, C(═O)NH(C1-C6-alkyl), CH(═S), C(═S)C1-C6-alkyl, C(═S)C2-C6-alkenyl, C(═S)C2-C6-alkynyl, C(═S)C3-C6-cycloalkyl, C(═S)O(C2-C6-alkenyl), C(═S)O(C2-C6-alkynyl), C(═S)O(C3-C7-cycloalkyl), C(═S)NH(C1-C6-alkyl), C(═S)NH(C2-C6-alkenyl), C(═S)NH(C2-C6-alkynyl), C(═S)NH(C3-C7-cycloalkyl),C(═S)N(C1-C6-alkyl)2, C(═S)N(C2-C6-alkenyl)2, C(═S)N(C2-C6-alkynyl)2, C(═S)N(C3-C7-cycloalkyl)2, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, ORY, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; wherein

    • Rx is as defined above;
    • RY is as defined above;
    • wherein the acyclic moieties of R3 are unsubstituted or substituted with groups R3a which independently of one another are selected from:
    • R3a halogen, OH, CN, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy, C1-C6-alkylthio, aryl and phenoxy, wherein the aryl and phenyl group is unsubstituted or substituted with substituents R31a selected from the group consisting of halogen, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy;
    • wherein the carbocyclic, heteroaryl and aryl moieties of R3 are unsubstituted or substituted with groups R3b which independently of one another are selected from:
    • R3b halogen, OH, CN, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy and C1-C6-alkylthio.


According to one embodiment of formula I, R3 is selected from the group consisting of halogen, CN, C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C1-C6-alkoxy, C1-C6-halogenalkoxy and ORY.


R3 is selected from the group consisting of halogen, CN, C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C1-C6-alkoxy, C1-C6-halogenalkoxy and ORY.


According to still another embodiment of formula I, R3 is halogen, in particular F, Cl, Br or I, more specifically F, Cl or Br, in particular F or Cl.


According to still another embodiment of formula I, R3 is F.


According to still another embodiment of formula I, R3 is Cl.


According to still another embodiment of formula I, R3 is Br.


According to still another embodiment of formula I, R3 is OH.


According to still another embodiment of formula I, R2 is COOH.


According to still another embodiment of formula I, R2 is CONH2.


According to still another embodiment of formula I, R3 is CN.


According to still another embodiment of formula I, R3 is NO2.


According to still another embodiment of formula I, R3 is SH.


According to still another embodiment of formula I, R3 is NH2.


According to still another embodiment of formula I, R3 is, NH(C1-C4-alkyl), in particular NH(CH3), NH(C2H5).


According to still another embodiment of formula I, R3 is, N(C1-C4-alkyl)2, in particular NH(CH3)2, NH(C2H5)2.


According to still another embodiment of formula I, R3 is NH(C2-C4-alkenyl), in particular NH(CH═CH2), NH(CH2CH═CH2).


According to still another embodiment of formula I, R3 is, N(C2-C4-alkenyl)2, in particular N(CH═CH2)2, N(CH2CH═CH2)2.


According to still another embodiment of formula I, R3 is, NH(C2-C4-alkynyl), in particular NH(C≡CH), NH(CH2C≡CH).


According to still another embodiment of formula I, R3 is, N(C2-C4-alkynyl)2, in particular N(C≡CH)2, N(CH2C≡CH)2.


According to still another embodiment of formula I, R3 is NH(C3-C6-cycloalkyl), in particular NH(C3H7), NH(C4H9).


According to still another embodiment of formula I, R3 is, N(C3-C6-cycloalkyl)2, in particular N(C3H7)2, N(C4H9)2.


According to still another embodiment of formula I, R3 is N(C1-C4-alkyl)(C2-C4-alkenyl), in particular N(CH3)(CH═CH2), N(CH3)(CH2CH═CH2), N(C2H5)(CH═CH2), N(C2H5)(CH2CH═CH2).


According to still another embodiment of formula I, R3 is N(C1-C4-alkyl)(C2-C4-alkynyl), in particular N(CH3)(C≡CH), N(CH3)(CH2C≡CH), N(C2H5)(C≡CH), N(C2H5)(CH2C≡CH).


According to still another embodiment of formula I, R3 is N(C1-C4-alkyl)(C3-C6-cycloalkyl), in particular N(CH3)(C3H7), N(CH3)(C4H9), N(C2H5)(C3H7), N(CH3)(C4H9).


According to still another embodiment of formula I, R3 is N(C2-C4-alkenyl)(C2-C4-alkynyl), in particular N(CH═CH2)(C≡CH), N(CH2CH═CH2)(CH2C≡CH), N(CH═CH2)(C≡CH), N(CH2CH═CH2)(CH2C≡CH).


According to still another embodiment of formula I, R3 is N(C2-C4-alkenyl)(C3-C6-cycloalkyl), in particular N(CH═CH2)(C3H7), N(CH2CH═CH2)(C4H9), N(CH═CH2)(C3H7), N(CH2CH═CH2)(C4H9).


According to still another embodiment of formula I, R3 is N(C2-C4-alkynyl)(C3-C6-cycloalkyl), in particular N(C≡CH)(C3H7), N(CH2C≡CH)(C4H9), N(C≡CH)(C3H7), N(CH2C≡CH)(C4H9).


According to still another embodiment of formula I, R3 is, NH(C(═O)(C1-C4-alkyl), in particular NH(C(═O)(CH3), NH(C(═O)(C2H5).


According to still another embodiment of formula I, R3 is N(C(═O)(C1-C4-alkyl)2, in particular N(C(═O)(CH3)2, N(C(═O)(C2H5)2.


According to a further specific embodiment of formula I, R3 is NH—SO2—Rx such as NH—SO2—CH3, NH—SO2—CH2—CH3, NH—SO2—CF3, NH—SO2-Ts.


According to still another embodiment of formula I, R3 is S(O)n—C1-C6-alkyl such as SCH3, S(═O) CH3, S(O)2CH3.


According to still another embodiment of formula I, R3 is S(O)n-aryl such as S-phenyl, S(═O) phenyl, S(O)2phenyl.


According to still another embodiment of formula I, R3 is S(O)n—C2-C6-alkenyl such as SCH═CH2, S(═O)CH═CH2, S(O)2CH═CH2, SCH2CH═CH2, S(═O)CH2CH═CH2, S(O)2CH2CH═CH2.


According to still another embodiment of formula I, R3 is S(O)n—C2-C6-alkynyl such as SC≡CH, S(═O)C≡CH, S(O)2C≡CH, SCH2C≡CH, S(═O)CH2C≡CH, S(O)2CH2C≡CH.


According to a further specific embodiment of formula I, R3 is CH(═O).


According to a further specific embodiment of formula I, R3 is C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl) or C(═O)NH(C1-C6-alkyl), wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.


According to a further specific embodiment of formula I, R3 is C(═O)C2-C6-alkenyl, C(═O)O(C2-C6-alkenyl) or C(═O)NH(C2-C6-alkenyl), wherein alkenyl is CH═CH2, C(CH3)═CH2, CH2CH═CH2.


According to a further specific embodiment of formula I, R3 is C(═O)C2-C6-alkynyl, C(═O)O(C2-C6-alkynyl) or C(═O)NH(C2-C6-alkynyl), wherein alkynyl is C≡CH, CH2C≡CH, According to a further specific embodiment of formula I, R3 is C(═O)C3-C6-cycloalkyl, C(═O)O(C3-C6-cycloalkyl) or C(═O)NH(C3-C6-cycloalkyl), wherein cycloalkyl is cyclopropyl (C3H7) or cyclobutyl (C4H9).


According to a further specific embodiment of formula I, R3 is CH(═S).


According to a further specific embodiment of formula I, R3 is C(═S)C1-C6-alkyl, C(═S)OC1-C6-alkyl, C(═S)NH(C1-C6-alkyl) or C(═S)NH(C1-C6-alkyl), wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.


According to a further specific embodiment of formula I, R3 is C(═S)C2-C6-alkenyl, C(═S)OC2-C6-alkenyl, C(═S)NH(C2-C6-alkenyl) or C(═S)N(C2-C6-alkenyl)2, wherein alkenyl is CH═CH2, CH2CH═CH2.


According to a further specific embodiment of formula I, R3 is C(═S)C2-C6-alkynyl, C(═S)O(C2-C6-alkynyl), C(═S)NH(C2-C6-alkynyl) or C(═S)N(C2-C6-alkynyl), wherein alkynyl is C≡CH, CH2C≡CH.


According to a further specific embodiment of formula I, R3 is C(═S)C3-C6-cycloalkyl, C(═S)O(C3-C7-cycloalkyl), C(═S)NH(C3-C7-cycloalkyl) or, C(═S)N(C3-C7-cycloalkyl)2, wherein cycloalkyl is cyclopropyl (C3H7) or cyclobutyl (C4H9).


According to still another embodiment of formula I, R3 is C1-C6-alkyl, in particular C1-C4-alkyl, such as CH3. or C2H5, in particular CH3 or CH2CH3.


According to still another embodiment of formula I, R3 is C1-C6-halogenalkyl, in particular C1-C4-halogenalkyl, such as CF3, CCl3, FCH2, ClCH2, F2CH, Cl2CH, CF3CH2, CCl3CH2 or CF2CHF2.


According to still a further embodiment of formula I, R3 is C2-C6-alkenyl, in particular C2-C4-alkenyl, such as CH═CH2.


According to a further specific embodiment of formula I, R3 is C2-C6-halogenalkenyl, in particular C2-C4-halogenalkenyl, more specifically C2-C3-halogenalkenyl such as CH═CHF, CH═CHCl, CH═CF2, CH═CCl2, CH2CH═CHF, CH2CH═CHCl, CH2CH═CF2, CH2CH═CCl2, CF2CH═CF2, CCl2CH═CCl2, CF2CF═CF2, CCl2CCl═CCl2.


According to still a further embodiment of formula I, R3 is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as C≡CH, CH2 C≡CH, C≡CCl, CH2C≡CCl, or CCl2C≡CCl.


According to a further specific embodiment of formula I, R3 is ORY, wherein RY is C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl.


According to a further specific embodiment of formula I, R3 is ORY, wherein RY is C1-C6-alkyl, in particular C1-C4-alkyl, more specifically C1-C2-alkoxy. R3 is such as OCH3 or OCH2CH3.


According to a further specific embodiment of formula I, R3 is ORY, wherein RY is C1-C6-halogenalkyl, in particular C1-C4-halogenalkyl, more specifically C1-C2-halogenalkyl. R3 is such as OCF3, OCHF2, OCH2F, OCCl3, OCHCl2 or OCH2Cl, in particular OCF3, OCHF2, OCCl3 or OCHCl2.


According to a further specific embodiment of formula I, R3 is ORY, wherein RY C2-C6-alkenyl, in particular C2-C4-alkenyl, more specifically C1-C2-alkenyl. R3 is such as OCH═CH2, OCH2CH═CH2.


According to a further specific embodiment of formula I, R3 is ORY, wherein RY C2-C6-alkynyl, in particular C2-C6-alkynyl, in particular C2-C4-alkynyl, more specifically C1-C2-alkynyl. R3 is such as OC≡CH, OC≡CCl, OCH2C≡CCl, or OCCl2C≡CCl


According to still another embodiment of formula I R3 is ORY, wherein RY is C3-C6-cycloalkyl, in particular cyclopropyl.


According to still another embodiment of formula I, R3 is ORY, wherein RY is C3-C6-halogencycloalkyl. In a special embodiment R1 is fully or partially halogenated cyclopropyl.


According to still another embodiment of formula I, R3 is is ORY, wherein RY C3-C6-cycloalkenyl, in particular cyclopropenyl.


According to still another embodiment of formula I, R3 is C3-C6-cycloalkyl, in particular cyclopropyl.


According to still another embodiment of formula I, R3 is C3-C6-halogencycloalkyl. In a special embodiment R3b is fully or partially halogenated cyclopropyl, such as 1-F-cyclopropyl, 1-Cl-cyclopropyl, 1,1-F2-cyclopropyl, 1,1-Cl2-cyclopropyl


According to still another embodiment of formula I, R3 is phenyl-C1-C6-alkyl, such as phenyl-CH2, wherein the phenyl moiety in each case is unsubstituted or substituted by one, two or three identical or different groups R3b which independently of one another are selected from halogen, C1-C2-alkyl, C1-C2-alkoxy, C1-C2-halogenalkyl and C1-C2-halogenalkoxy, in particular F, Cl, Br, CH3, OCH3, CF3 and OCF3.


According to still another embodiment of formula I, R3 is aryl, in particular phenyl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted with identical or different groups R3b which independently of one another are selected from CN, halogen, C1-C2-alkyl, C1-C2-alkoxy, C1-C2-halogenalkyl and C1-C2-halogenalkoxy, in particular CN, F, Cl, Br, CH3, OCH3, CHF2, OCHF2, CF3 and OCF3. According to one embodiment, R3 is unsubstituted phenyl. According to another embodiment, R3 is phenyl, that is substituted with one, two or three, in particular one, halogen, in particular selected from F, Cl and Br, more specifically selected from F and Cl.


According to still another embodiment of formula I, R3 is a 5-membered heteroaryl such as pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,2,4-triazolyl-1-yl, 1,2,4-triazol-3-yl 1,2,4-triazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl and 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl.


According to still another embodiment of formula I, R3 is a 6-membered heteroaryl such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl and 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl.


According to still another embodiment of formula I, R3 is in each case independently selected from halogen, CN, C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1-C6-halogenalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl and C3-C6-halogencycloalkyl, wherein the acyclic moieties of R3 are unsubstituted or substituted with identical or different groups R3a as defined and preferably defined herein, and wherein the carbocyclic, phenyl and heteroaryl moieties of R3 are unsubstituted or substituted with identical or different groups R3b as defined and preferably defined herein.


According to still another embodiment of formula I, R3 is in each case independently selected from halogen, CN, C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1-C6-halogenalkoxy; wherein the acyclic moieties of R3 are unsubstituted or substituted with identical or different groups R3a as defined and preferably defined herein.


According to still another embodiment of formula I, R3 is in each case independently selected from CN, halogen, C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkynyl, ORY, C3-C6-cycloalkyl; wherein RY is C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl or C2-C6-alkynyl.


R3a are the possible substituents for the acyclic moieties of R3.


According to one embodiment R3a is independently selected from halogen, OH, CN, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy, C1-C6-alkylthio, aryl and phenoxy, wherein the aryl and phenyl group is unsubstituted or substituted with substituents R31a selected from the group consisting of halogen, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy.


According to one embodiment R3a is independently selected from halogen, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C4-halogenalkoxy. Specifically, R3a is independently selected from F, Cl, Br, I, C1-C2-alkoxy, cyclopropyl, 1-F-cyclopropyl, 1-Cl-cyclopropyl, 1,1-F2-cyclopropyl, 1,1-Cl2-cyclopropyl and C1-C2-halogenalkoxy.


According to still another embodiment of formula I, R3a is independently halogen, in particular selected from F, Cl, Br and I, more specifically F, Cl and Br.


R3b are the possible substituents for the carbocyclic, heteroaryl and phenyl moieties of R3. R3b according to the invention is independently selected from halogen, OH, CN, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy and C1-C6-alkylthio.


According to one embodiment thereof R3b is independently selected from halogen, CN, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl and C1-C4-halogenalkoxy, in particular halogen, C1-C4-alkyl and C1-C4-alkoxy. Specifically, R3b is independently selected from F, Cl, CN, CH3, OCH3 and halogenmethoxy.


Particularly preferred embodiments of R3 according to the invention are in Table P3 below, wherein each line of lines P3-1 to P3-41 corresponds to one particular embodiment of the invention, wherein P3-1 to P3-41 are also in any combination with one another a preferred embodiment of the present invention. The connection point to the carbon atom, to which R3 is bound is marked with “#” in the drawings.












TABLE P3







No.
R3









P3-1
CH3



P3-2
CH2F



P3-3
CHF2



P3-4
CF3



P3-5
C2H5



P3-6
CH(CH3)2



P3-7
CH2CH2CH3



P3-8
CH2CH2CH2CH3



P3-9
CH2CH(CH3)2



P3-10
C(CH3)3



P3-11
CH2CH2CH2CH2CH3



P3-12
CH═CH2



P3-13
CH2CH═CH2



P3-14
C≡CH



P3-15
CH2C≡CH



P3-16
CH2CH2CH(CH3)2



P3-17
OH



P3-18
OCH3



P3-19
OCHF2



P3-20
OC2H5



P3-21
CN



P3-22
F



P3-23
Cl



P3-24
Br



P3-25
NO2



P3-26
NH2



P3-27
CO—NH2



P3-28
CO—NH(CH3)



P3-29
HNCH3



P3-30
HNC2H5



P3-31
(CH3)2N



P3-32
SO2H



P3-33
SO2—CH3



P3-34
SO—CH3



P3-35
S—CH3







P3-36


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P3-37


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P3-38


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P3-39


embedded image









P3-40


embedded image









P3-41


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According to still another embodiment of formula I, R2, R3 together with the carbon atoms to which they are bound form a five-, six-, or seven-membered carbo-, heterocyclic or heteroaromatic ring; wherein the heterocyclic or heteroaromatic ring contains 1, 2, 3 or 4 heteroatoms selected from N, O and S, wherein N may carry one substituent RN selected from C1-C4-alkyl, C1-C4-halogenalkyl and SO2Ph, wherein Ph is unsubstituted or substituted by substituents selected from C1-C4-alkyl, halogen, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, and CN; and wherein S may be in the form of its oxide SO or SO2; and wherein in each case one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(═O) and C(═S); and wherein the carbo-, heterocyclic or heteroaromatic ring is substituent by (R23)m, wherein m is 0, 1, 2, 3 or 4;

    • R23 is in each case independently selected from halogen, OH, CN, COOH, CONH2, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C3-C6-cycloalkyl, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl and aryl; wherein the heterocycle and heteroaryl contains 1, 2 or 3 heteroatoms selected from N, O and S; and wherein in each case one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(═O) and C(═S); and wherein
    • Rx is as defined above;


wherein the acyclic moieties of R23 are unsubstituted or carry 1, 2, 3 or up to the maximum possible number of identical or different groups R23a which independently of one another are selected from:

    • R23a halogen, OH, CN, COOH, CONH2, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy, C1-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R91a selected from the group consisting of halogen, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, CN, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-alkylthio;


wherein the carbocyclic, heterocyclic, heteroaryl and aryl moieties of R23 are unsubstituted or substituted with identical or different groups R23b which independently of one another are selected from:

    • R23b halogen, OH, CN, COOH, CONH2, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy, and C1-C6-alkylthio.


According to still another embodiment of formula I, R2, R3 together with the carbon atoms to which they are bound form a five-, six-, or seven-membered carbo-, heterocyclic or heteroaromatic ring; wherein the heterocyclic or heteroaromatic ring contains 1, 2, 3 or 4 heteroatoms selected from N, O and S, wherein N may carry one substituent RN selected from C1-C4-alkyl, C1-C4-halogenalkyl and SO2Ph, wherein Ph is unsubstituted or substituted with substituents selected from C1-C4-alkyl, halogen, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy, and CN; and wherein S may be in the form of its oxide SO or SO2; and wherein in each case one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(═O) and C(═S); and wherein the carbo-, heterocyclic or heteroaromatic ring is substituent by (R23)m wherein m is 0, 1, 2, 3 or 4;


RN is the substituent of the heteroatom N that is contained in the heterocycle formed by R2 and R3 in some of the inventive compounds. RN is selected from C1-C4-alkyl, C1-C4-halogenalkyl and SO2Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted with one, two or three substituents selected from C1-C4-alkyl. In one preferred embodiment, RN is in each case independently selected from C1-C2-alkyl, C1-C2-halogenalkyl and SO2Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted with one methyl substituents. In one particular embodiment, RN is in each case independently selected from C1-C2-alkyl, more particularly methyl. In one particular embodiment, RN is in each case independently selected from SO2Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted with one methyl.


According to still another embodiment of formula I, R2 and R3 together with the carbon atoms to which they are bound form a saturated or partially unsaturated five-, six-or seven-membered carbo- and heterocycle that is unsubstituted or substituted.


According to one embodiment, R2 and R3 form a 3-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R23. According to still another embodiment of formula I, it is substituted with R23.


According to one embodiment, R2 and R3 form a 4-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R23. According to still another embodiment of formula I, it is substituted with R23.


According to one embodiment, R2 and R3 form a 5-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R23. According to still another embodiment of formula I, it is substituted with R23.


According to one embodiment, R2 and R3 form a 6-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R23. According to still another embodiment of formula I, it is substituted with R23.


According to one embodiment, R2 and R3 form a 7-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R23. According to still another embodiment of formula I, it is substituted with R23.


According to one embodiment, R2 and R3 form a 3-membered saturated heterocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R23. According to still another embodiment of formula I, it is substituted with R23.


According to one embodiment, R2 and R3 form a 4-membered saturated heterocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R23. According to still another embodiment of formula I, it is substituted with R23.


According to one embodiment, R2 and R3 form a 5-membered saturated heterocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R23. According to still another embodiment of formula I, it is substituted with R23.


According to one embodiment, R2 and R3 form a 6-membered saturated heterocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R23. According to still another embodiment of formula I, it is substituted with R23.


According to one embodiment, R2 and R3 form a 7-membered saturated heterocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R23. According to still another embodiment of formula I, it is substituted with R23.


According to one embodiment, R2 and R3 form a 5-membered saturated heteroaryl. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R23. According to still another embodiment of formula I, it is substituted with R23.


According to one embodiment, R2 and R3 form a 6-membered heteroaryl. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R23.


According to still another embodiment of formula I, it is substituted with R23.


According to one embodiment, R2 and R3 do not form a cyclic substituent.


R23 according to the invention is in each case independently selected from halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl and aryl;


wherein the heterocycle and heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein in each case one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(═O) and C(═S); and wherein


Rx is as defined above;


wherein the acyclic moieties of R23 are unsubstituted or substituted with identical or different groups R23a which independently of one another are selected from:


R23a halogen, OH, CN, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy, C1-C6-alkylthio, aryl and phenoxy, wherein the aryl group is unsubstituted or unsubstituted or substituted with R23a selected from the group consisting of halogen, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, CN, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-alkylthio;


wherein the carbocyclic, heterocyclic, heteroaryl and aryl of R23 are unsubstituted or substituted with identical or different groups R23b which independently of one another are selected from:


R23b halogen, OH, CN, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy and C1-C6-alkylthio.


For every R23 that is present in the inventive compounds, the following embodiments and preferences apply independently of the meaning of any other R23 that may be present in the ring.


According to one embodiment of formula I, wherein m is 0, 1, 2, 3 or 4.


According to still another embodiment of formula I, m is 0.


According to still another embodiment of formula I, m is 1.


According to still another embodiment of formula I, m is 2 or 3. According to one specific embodiment thereof, m is 2. According to still another embodiment of formula I, m is 3.


According to one embodiment of formula I, R23 is halogen, C1-C6-alkyl, C1-C6-halogenalkyl, C1-C6-alkoxy or, C1-C6-halogenalkoxy, in particular CH3, Et, CHF2, OCH3, OCHF2, OCF3, F, Cl, more specifically H, CH3, F or Cl most preferred F or Cl.


According to still another embodiment of formula I, R23 is halogen, in particular Br, F or Cl, more specifically F or Cl.


According to still another embodiment of formula I, R23 is OH.


According to still another embodiment of formula I, R23 is CN.


According to still another embodiment of formula I R23 is NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2 or NH—SO2—Rx, wherein Rx is C1-C4-alkyl, C1-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted with one, two, three, four or five substituents Rx23 independently selected from C1-C4-alkyl.


According to still another embodiment of formula I, R23 is C1-C6-alkyl, in particular C1-C4-alkyl, such as CH3.


According to still another embodiment of formula I, R23 is C1-C6-halogenalkyl, in particular C1-C4-halogenalkyl, such as CF3, CHF2, CH2F, CCl3, CHCl2 or CH2Cl.


According to still another embodiment of formula I, R23 is C2-C6-alkenyl or C2-C6-halogenalkenyl, in particular C2-C4-alkenyl or C2-C4-halogenalkenyl, such as CH═CH2, C(CH3)═CH2, CH2CH═CH2, CH═CHF, CH═CHCl, CH═CF2, CH═CCl2, CF═CF2, CCl═CCl2, CH2CH═CHF, CH2CH═CHCl, CH2CH═CF2, CH2CH═CCl2, CH2CF═CF2, CH2CCl═CCl2, CF2CF═CF2 or CCl2CCl═CCl2.


According to still another embodiment of formula I, R23 is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as C≡CH, CH2C≡CH, C≡C—Cl, C≡C—CH3, CH2C≡CH, CH2C≡CCl or CH2C≡C—CH3.


According to still another embodiment of formula I, R23 is C1-C6-alkoxy, in particular C1-C4-alkoxy, more specifically C1-C2-alkoxy such as OCH3 or OCH2CH3.


According to still another embodiment of formula I, R23 is C1-C6-halogenalkoxy, in particular C1-C4-halogenalkoxy, more specifically C1-C2-halogenalkoxy such as OCF3, OCHF2, OCH2F, OCCl3, OCHCl2 or OCH2Cl, in particular OCF3, OCHF2, OCCl3 or OCHCl2.


According to still another embodiment of formula I R23 is C3-C6-cycloalkyl, in particular cyclopropyl.


According to still another embodiment of formula I, R23 is C3-C6-cycloalkyl, for example cyclopropyl, substituted with one, two, three or up to the maximum possible number of identical or different groups R23b as defined and preferably herein.


According to still another embodiment of formula I, R23 is C3-C6-halogencycloalkyl. In a special embodiment R23 is fully or partially halogenated cyclopropyl.


According to still another embodiment of formula I, R23 is unsubstituted aryl or aryl that is substituted with one, two, three or four R23b, as defined herein. In particular, R23 is unsubstituted phenyl or phenyl that is substituted with one, two, three or four R23b, as defined herein.


According to still another embodiment of formula I, R23 is unsubstituted 5- or 6-membered heteroaryl. According to still a further embodiment, R23 is 5- or 6-membered heteroaryl that is substituted with one, two or three R23b, as defined herein.


According to still another embodiment of formula I, R23 is in each case independently selected from halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy and C3-C6-cycloalkyl; wherein the acyclic moieties of R23 are not further substituted or carry one, two, three, four or five identical or different groups R23a as defined below and wherein the carbocyclic, heterocyclic and heteroaryl moieties of R23 are not further substituted or carry one, two, three, four or five identical or different groups R23b as defined below.


According to still another embodiment of formula I, R23 is independently selected from halogen, OH, C1-C6-alkyl, C1-C6-halogenalkyl, C1-C6-alkoxy and C1-C6-halogenalkoxy, in particular independently selected from F, Cl, Br, CN, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy.


R23a are the possible substituents for the acyclic moieties of R23.


R23a according to the invention is independently selected from halogen, OH, CN, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy, C1-C6-alkylthio, aryl and phenoxy, wherein the aryl and phenyl group is unsubstituted or unsubstituted or substituted with R23a selected from the group consisting of halogen, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, CN, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-alkylthio.


R23a according to the invention is independently selected from halogen, OH, CN, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy, C1-C6-alkylthio, aryl and phenoxy, wherein the aryl and phenyl group is unsubstituted or unsubstituted or substituted with R23a selected from the group consisting of halogen, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy, in particular selected from halogen, C1-C2-alkyl, C1-C2-halogenalkyl, C1-C2-alkoxy, C1-C2-halogenalkoxy, more specifically selected from halogen, such as F, Cl and Br.


In to one embodiment R23a is independently selected from halogen, OH, CN, C1-C2-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C2-halogenalkoxy. Specifically, R23a is independently selected from F, Cl, OH, CN, C1-C2-alkoxy, cyclopropyl, 1-F-cyclopropyl, 1-Cl-cyclopropyl, 1,1-F2-cyclopropyl, 1,1-Cl2-cyclopropyl and C1-C2-halogenalkoxy.


According to one embodiment R23a is independently selected from halogen, such as F, Cl, Br and I, more specifically F, Cl and Br.


According to still another embodiment of formula I, R23a is independently selected from OH, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C2-halogenalkoxy. Specifically, R23a is independently selected from OH, cyclopropyl and C1-C2-halogenalkoxy.


R23b are the possible substituents for the carbocyclic, heterocyclic and heteroaryl moieties of R23.


R23b according to the invention is independently selected from halogen, OH, CN, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C4-halogenalkoxy.


According to one embodiment thereof R23b is independently selected from halogen, CN, C1-C2-alkyl, C1-C2-alkoxy, C1-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalky and C1-C2-halogenalkoxy. Specifically, R23b is independently selected from F, Cl, OH, CN, CH3, OCH3, cyclopropyl, 1-F-cyclopropyl, 1-Cl-cyclopropyl, 1,1-F2-cyclopropyl, 1,1-Cl2-cyclopropyl and halogenmethoxy.


According to still another embodiment thereof R23b is independently selected from C1-C2-alkyl, C1-C2-alkoxy, C1-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C2-halogenalkoxy. Specifically, R23b is independently selected from OH, CH3, OCH3, cyclopropyl, 1-F-cyclopropyl, 1-Cl-cyclopropyl, 1,1-F2-cyclopropyl, 1,1-Cl2-cyclopropyl and halogenmethoxy, more specifically independently selected from OH, CH3, OCH3, cyclopropyl, 1-F-cyclopropyl, 1-Cl-cyclopropyl, 1,1-F2-cyclopropyl, 1,1-Cl2-cyclopropyl cyclopropyl and OCHF2.


Particularly preferred embodiments of combinations of R2 and R3 according to the invention are in Table P35 below, wherein each line of lines P35-1 to P35-305 corresponds to one particular embodiment of the invention, wherein P35-1 to P35-305 are also in any combination with one another a preferred embodiment of the present invention. The carbon atom, to which R2 bound is marked with * in the drawings and the carbon atom, to which R3 is bound is marked with # in the drawings. cPr stands for cyclopropyl.













TABLE P23







line
R2
R3



















P23-1


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P23-2


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P23-3


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P23-4


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P23-5


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P23-6


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P23-7


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P23-8


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P23-9


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P23-10


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P23-11


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P23-12


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P23-13


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P23-14


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P23-15


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P23-16


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R4 according to the invention is in each case independently selected from hydrogen, halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl;


wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; and


wherein


Rx is C1-C4-alkyl, C1-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted with one, two, three, four or five substituents Rx4 independently selected from C1-C4-alkyl, halogen, OH, ON, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy;


wherein the acyclic moieties of R4 are unsubstituted or substituted with identical or different groups R4a which independently of one another are selected from:


R4a halogen, OH, CN, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalky, C1-C4-halogenalkoxy, C1-C6-alkylthio, aryl and phenoxy, wherein the aryl and phenoxy group is unsubstituted or unsubstituted or substituted with R44a selected from the group consisting of halogen, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy;


wherein the carbocyclic, heteroaryl and aryl moieties of R4 are unsubstituted or substituted with identical or different groups R4b which independently of one another are selected from:


R4b halogen, OH, CN, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy and C1-C6-alkylthio.


For every R4 that is present in the inventive compounds, the following embodiments and preferences apply independently of the meaning of any other R4 that may be present in the ring.


According to one embodiment of formula I, R4 is H, halogen or C1-C6-alkyl, in particular H, CH3, Et, F, Cl, more specifically H, CH3, F or Cl most preferred H, F or Cl.


According to another embodiment of formula I, R4 is hydrogen.


According to still another embodiment of formula I, R4 is halogen, in particular Br, F or Cl, more specifically F or Cl.


According to another embodiment of formula I, R4 is F


According to another embodiment of formula I, R4 is Cl


According to another embodiment of formula I, R4 is Br.


According to still another embodiment of formula I, R4 is OH.


According to still another embodiment of formula I, R4 is COOH.


According to still another embodiment of formula I, R4 is CONH2.


According to still another embodiment of formula I, R4 is CN.


According to still another embodiment of formula I, R4 is NO2.


According to still another embodiment of formula I, R4 is SH.


According to still another embodiment of formula I R4 is NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2 or NH—SO2—Rx, wherein Rx is C1-C4-alkyl, C1-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted with one, two, three, four or five substituents Rx4 independently selected from C1-C4-alkyl, halogen, OH, CN, C1-C4-halogenalkyl, C1-C4-alkoxy, or C1-C4-halogenalkoxy. In particular C1-C4-alkyl, such as NHCH3 and N(CH3)2. In particular Rx is C1-C4-alkyl, and phenyl that is substituted with one CH3, more specifically SO2—Rx is CH3 and tosyl group (“Ts”).


According to still another embodiment of formula I, R4 is C1-C6-alkyl, in particular C1-C4-alkyl, such as CH3 or CH2CH3.


According to still another embodiment of formula I, R4 is C1-C6-halogenalkyl, in particular C1-C4-halogenalkyl, such as CF3, CHF2, CH2F, CCl3, CHCl2, CH2Cl, CF3CH2, CCl3CH2 or CF2CHF2.


According to still another embodiment of formula I, R4 is C2-C6-alkenyl or C2-C6-halogenalkenyl, in particular C2-C4-alkenyl or C2-C4-halogenalkenyl, such as CH═CH2, C(CH3)═CH2, CH═CCl2, CH═CF2, CCl═CCl2, CF═CF2, CH═CH2, CH2CH═CCl2, CH2CH═CF2, CH2CCl═CCl2, CH2CF═CF2, CCl2CH═CCl2, CF2CH═CF2, CCl2CCl═CCl2, or CF2CF═CF2.


According to still another embodiment of formula I, R4 is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as C≡CH, C≡CCl, C≡CF. CH2C≡CH, CH2C≡CCl, or CH2C≡CF.


According to still another embodiment of formula I, R4 is C1-C6-alkoxy, in particular C1-C4-alkoxy, more specifically C1-C2-alkoxy such as OCH3 or OCH2CH3.


According to still another embodiment of formula I, R4 is C1-C6-halogenalkoxy, in particular C1-C4-halogenalkoxy, more specifically C1-C2-halogenalkoxy such as OCF3, OCHF2, OCH2F, OCCl3, OCHCl2 or OCH2Cl, in particular OCF3, OCHF2, OCCl3 or OCHCl2.


According to still another embodiment of formula I R4 is C3-C6-cycloalkyl, in particular cyclopropyl.


According to still another embodiment of formula I, R4 is C3-C6-cycloalkyl, for example cyclopropyl, substituted with one, two, three or up to the maximum possible number of identical or different groups R4b as defined and preferably herein.


According to still another embodiment of formula I, R4 is C3-C6-halogencycloalkyl. In a special embodiment R4 is fully or partially halogenated cyclopropyl.


According to still another embodiment of formula I, R4 is unsubstituted aryl or aryl that is substituted with one, two, three or four R4b, as defined herein. In particular, R4 is unsubstituted phenyl or phenyl that is substituted with one, two, three or four R4b, as defined herein.


According to still another embodiment of formula I, R4 is unsubstituted 5- or 6-membered heteroaryl. According to still a further embodiment, R4 is 5- or 6-membered heteroaryl that is substituted with one, two or three R4b, as defined herein.


According to still another embodiment of formula I, R4 is in each case independently selected from hydrogen, halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy and C3-C6-cycloalkyl; wherein the acyclic moieties of R4 are not further substituted or carry one, two, three, four or five identical or different groups R4a as defined below and wherein the carbocyclic, heteroaryl and aryl moieties of R4 are not further substituted or carry one, two, three, four or five identical or different groups R4b as defined below.


According to still another embodiment of formula I, R4 is independently selected from hydrogen, halogen, CN, OH, C1-C6-alkyl, C1-C6-alkoxy, C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, wherein the acyclic and cyclic moieties of R4 are unsubstituted or substituted by halogen.


According to still another embodiment of formula I, R4 is independently selected from hydrogen, halogen, CN, OH, C1-C6-alkyl, C1-C6-halogenalkyl, C1-C6-alkoxy and C1-C6-halogenalkoxy, in particular independently selected from H, F, Cl, Br, CN, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy.


According to still another embodiment of formula I, R4 is independently selected from H, CN, halogen or C1-C6-alkyl, in particular H, CN, CH3, Et, F, Cl, more specifically H, CN, CH3, F or Cl most preferred H, CH3, F or Cl.


R4a are the possible substituents for the acyclic moieties of R4.


R4a according to the invention is independently selected from halogen, OH, CN, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy, C1-C6-alkylthio, aryl and phenoxy, wherein the aryl group is unsubstituted or unsubstituted or substituted with R44a selected from the group consisting of halogen, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy, in particular selected from halogen, C1-C2-alkyl, C1-C2-halogenalkyl, C1-C2-alkoxy and C1-C2-halogenalkoxy, more specifically selected from halogen, such as F, Cl and Br.


In to one embodiment R4a is independently selected from halogen, OH, CN, C1-C2-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C2-halogenalkoxy. Specifically, R4a is independently selected from F, Cl, OH, CN, C1-C2-alkoxy, cyclopropyl, 1-F-cyclopropyl, 1-Cl-cyclopropyl, 1,1-F2-cyclopropyl, 1,1-Cl2-cyclopropyl and C1-C2-halogenalkoxy.


According to one embodiment R4a is independently selected from halogen, such as F, Cl, Br and I, more specifically F, Cl and Br.


According to still another embodiment of formula I, R4a is independently selected from OH, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C2-halogenalkoxy. Specifically, R4a is independently selected from OH, cyclopropyl and C1-C2-halogenalkoxy.


According to still another embodiment of formula I, R4a is independently selected from aryl and phenoxy, wherein the aryl group is unsubstituted or substituted with R44a selected from the group consisting of halogen, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy, in particular selected from halogen, C1-C2-alkyl, C1-C2-halogenalkyl, C1-C2-alkoxy and C1-C2-halogenalkoxy, more specifically selected from halogen, such as F, Cl and Br.


R4b are the possible substituents for the carbocyclic, heteroaryl and aryl moieties of R4.


R4b according to the invention is independently selected from halogen, OH, CN, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy and C1-C6-alkylthio;


According to one embodiment thereof R4b is independently selected from halogen, CN, C1-C2-alkyl, C1-C2-alkoxy, C1-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C2-halogenalkoxy. Specifically, R4b is independently selected from F, Cl, Br, OH, CN, CH3, OCH3, CHF2, OCHF2, cyclopropyl, 1-F-cyclopropyl, 1-Cl-cyclopropyl, 1,1-F2-cyclopropyl, 1,1-Cl2-cyclopropyl, OCF3, and OCHF2.


According to still another embodiment thereof R4b is independently selected from halogen, C1-C2-alkyl, C1-C2-alkoxy, C1-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C2-halogenalkoxy. Specifically, R4b is independently selected from halogen, CN, OH, CH3, CHF2, OCHF2, OCF3, OCH3, cyclopropyl, 1-F-cyclopropyl, 1-Cl-cyclopropyl, 1,1-F2-cyclopropyl, 1,1-Cl2-cyclopropyl and halogenmethoxy, more specifically independently selected from F, Cl, OH, CH3, OCH3, CHF2, OCH3, cyclopropyl, 1-F-cyclopropyl, 1-Cl-cyclopropyl, 1,1-F2-cyclopropyl, 1,1-Cl2-cyclopropyl, OCHF2 and OCF3.


Rx in the substituent NH—SO2—Rx is in each case independently selected from C1-C4-alkyl, C1-C4-halogenalkyl, unsubstituted aryl and aryl that is substituted with one, two, three, four or five substituents Rx4 independently selected from C1-C4-alkyl, halogen, OH, CN, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy. In particular, Rx is in each case independently selected from C1-C4-alkyl, halogen, OH, CN and phenyl that is substituted with one, two or three Rx4 independently selected from C1-C2-alkyl, more specifically Rx is in each case independently selected from C1-C4-alkyl and phenyl that is substituted with one CH3, more specifically SO2—Rx is the tosyl group (“Ts”).


Particularly preferred embodiments of R4 according to the invention are in Table P4 below, wherein each line of lines P4-1 to P4-16 corresponds to one particular embodiment of the invention. Thereby, for every R4 that is present in the inventive compounds, these specific embodiments and preferences apply independently of the meaning of any other R4 that may be present in the ring:












TABLE P4







No.
R4









P4-1
H



P4-2
Cl



P4-3
F



P4-4
Br



P4-5
OH



P4-6
ON



P4-7
NO2



P4-8
CH3



P4-9
CH2CH3



P4-10
CF3



P4-11
CHF2



P4-12
OCH3



P4-13
OCH2CH3



P4-14
OCF3



P4-15
OCHF2



P4-16
NH-Ts







“Ts” in the table stands for the tosylgroup SO2-(p-CH3)phenyl.






R5 is in each case independently selected from hydrogen, OH, CH(═O), C(═O)C1-C6-alkyl, C(═O)C2-C6-alkenyl, C(═O)C3-C6-cycloalkyl, C1-C6-alkyl, C1-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, ORY, C2-C6-alkenyl, C2-C6-halogenalkenyl C2-C6-alkynyl, C2-C6-halogenalkynyl, S(O)n—C1-C6-alkyl, S(O)n—C1-C6-halogenalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; wherein the aryl groups are unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of CN, halogen, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy; wherein n and RY are as defined above.


R5a is the substituent of the acyclic moieties of R5. The acyclic moieties of R5 are not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R5a which independently of one another are selected from halogen, OH, CN, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6-halogencycloalkyl, C3-C6-halogencycloalkenyl, C1-C4-halogenalkoxy, C1-C6-alkylthio, five- or six-membered heteroaryl, aryl and phenoxy, wherein the heteroaryl, aryl and phenoxy group is unsubstituted or carries one, two, three, four or five substituents R78a′ selected from the group consisting of halogen, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy;


R5b is the substituent of carbocyclic, phenyl, heterocyclic and heteroaryl moieties of R5. The carbocyclic, phenyl, heterocyclic and heteroaryl moieties of R5 are not further substituted or carry one, two, three, four, five or up to the maximum number of identical or different groups R5b which independently of one another are selected from halogen, OH, CN, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy and C1-C6-alkylthio.


According to one embodiment of formula I, R5 is H.


According to still another embodiment of formula I, R5 is OH.


According to a further specific embodiment of formula I, R5 is CH(═O).


According to a further specific embodiment of formula I, R5 is C(═O)C1-C6-alkyl, wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.


According to a further specific embodiment of formula I, R5 is C(═O)C2-C6-alkenyl, wherein alkenyl is CH═CH2, CH2CH═CH2.


According to a further specific embodiment of formula I, R5 is C(═O)C2-C6-alkynyl wherein alkynyl is C≡CH, CH2C≡CH.


According to a further specific embodiment of formula I, R5 is C(═O)C3-C6-cycloalkyl, wherein cycloalkyl is cyclopropyl (C3H7) or cyclobutyl (C4H9).


According to still another embodiment of formula I, R5 is C1-C6-alkyl, such as CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.


According to still another embodiment of formula I, R5 is C1-C6-alkyl, in particular C1-C4-alkyl, such as CH3, C2H5, n-propyl, i-propyl.


According to still another embodiment of formula I, R5 is C1-C6-halogenalkyl, in particular C1-C4-halogenalkyl, such as CF3, CCl3, FCH2, ClCH2, F2CH, Cl2CH, CF3CH2, CCl3CH2 or CF2CHF2.


According to still another embodiment of formula I R5 is C3-C6-cycloalkyl, in particular cyclopropyl.


According to still another embodiment of formula I, R5 is C3-C6-halogencycloalkyl. In a special embodiment R5b is fully or partially halogenated cyclopropyl, such as 1-F-cyclopropyl, 1-Cl-cyclopropyl, 1,1-F2-cyclopropyl, 1,1-Cl2-cyclopropyl.


According to still another embodiment of formula I, R5 is C1-C4-alkoxy and C1-C4-halogenalkoxy, in particular C1-C3-alkoxy, C1-C3-halogenalkoxy, such as CH2OCH3, CH2OCF3 or CH2OCHF2.


According to a further specific embodiment of formula I, R5 is ORY, wherein RY is C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, phenyl and phenyl-C1-C6-alkyl; wherein the phenyl groups are unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of CN, halogen, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy;


According to a further specific embodiment of formula I, R5 is ORY, wherein RY is C1-C6-alkyl, in particular C1-C4-alkyl, more specifically C1-C2-alkyl. R5 is such as OCH3 or OCH2CH3.


According to a further specific embodiment of formula I, R5 is ORY, wherein RY is C1-C6-halogenalkyl, in particular C1-C4-halogenalkyl, more specifically C1-C2-halogenalkyl. R5 is such as OCF3, OCHF2, OCH2F, OCCl3, OCHCl2 or OCH2Cl, in particular OCF3, OCHF2, OCCl3 or OCHCl2.


According to a further specific embodiment of formula I, R5 is ORY, wherein RY C2-C6-alkenyl, in particular C2-C4-alkenyl, more specifically C1-C2-alkenyl. R5 is such as OCH═CH2, OCH2CH═CH2.


According to a further specific embodiment of formula I, R5 is ORY, wherein RY C2-C6-alkynyl, in particular C2-C6-alkynyl, in particular C2-C4-alkynyl, more specifically C1-C2-alkynyl. R5 is such as OC≡CH


According to still another embodiment of formula I, R5 is ORY, wherein RY is C3-C6-halogencycloalkyl. In a special embodiment R1 is fully or partially halogenated cyclopropyl.


According to still another embodiment of formula I, R5 is is ORY, wherein RY and phenyl; wherein the phenyl groups are unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of CN, halogen, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy.


According to still another embodiment of formula I, R5 is is ORY, wherein RY phenyl-C1-C6-alkyl, such as phenyl-CH2, herein the phenyl groups are unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of CN, halogen, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy. R5 is such as OCH2Ph.


According to still a further embodiment of formula I, R5 is C2-C6-alkenyl, in particular C2-C4-alkenyl, such as CH═CH2, C(CH3)═CH2, CH2CH═CH2.


According to a further specific embodiment of formula I, R5 is C2-C6-halogenalkenyl, in particular C2-C4-halogenalkenyl, more specifically C2-C3-halogenalkenyl such as CH═CHF, CH═CHCl, CH═CF2, CH═CCl2, CH2CH═CHF, CH2CH═CHCl, CH2CH═CF2, CH2CH═CCl2, CF2CH═CF2, CCl2CH═CCl2, CF2CF═CF2, CCl2CCl═CCl2.


According to still a further embodiment of formula I, R5 is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as C≡CH, CH2C≡CH.


According to still another embodiment of formula I, R5 is phenyl-C1-C6-alkyl, such as phenyl-CH2, wherein the phenyl moiety in each case is unsubstituted or substituted by one, two or three identical or different groups R5b which independently of one another are selected from halogen, C1-C2-alkyl, C1-C2-alkoxy, C1-C2-halogenalkyl and C1-C2-halogenalkoxy, in particular F, Cl, Br, CH3, OCH3, CF3 and OCF3.


According to still another embodiment of formula I, R5 is aryl, in particular phenyl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted by identical or different groups R5b which independently of one another are selected from halogen, C1-C2-alkyl, C1-C2-alkoxy, C1-C2-halogenalkyl and C1-C2-halogenalkoxy, in particular F, Cl, Br, CH3, OCH3, CF3 and OCF3. According to one embodiment, R5 is unsubstituted phenyl. According to another embodiment, R5 is phenyl, that is substituted by one, two or three, in particular one, halogen, in particular selected from F, Cl and Br, more specifically selected from F and Cl.


According to still another embodiment of formula I, R5 is a 5-membered heteroaryl such as pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,2,4-triazolyl-1-yl, 1,2,4-triazol-3-yl 1,2,4-triazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl and 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl.


According to still another embodiment of formula I, R5 is a 6-membered heteroaryl such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl and 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl.


According to still another embodiment of formula I, R5 is in each case independently selected from H, halogen, OH, CN, C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1-C6-halogenalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy and C3-C6-cycloalkyl wherein the acyclic moieties of R5 are unsubstituted or substituted with identical or different groups R5a as defined and preferably defined herein, and wherein the carbocyclic, phenyl and heteroaryl moieties of R5 are unsubstituted or substituted with identical or different groups R5b as defined and preferably defined herein.


According to still another embodiment of formula I, R5 is in each case independently selected from H, halogen, OH, CN, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy and C3-C6-cycloalkyl, wherein the acyclic moieties of R5 are unsubstituted or substituted with identical or different groups R5a as defined and preferably defined herein, and wherein the cycloalkyl moieties of R5 are unsubstituted or substituted with identical or different groups R5b as defined and preferably defined herein.


According to still another embodiment of formula I, R5 is in each case independently selected from H and ORY, wherein RY is most preferably C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, phenyl and phenyl-C1-C6-alkyl; wherein the phenyl groups are unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of CN, halogen, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy.


According to still another embodiment of formula I, R5 is in each case independently selected from H and ORY, wherein RY is most preferably C2-C6-alkenyl, C2-C6-alkynyl, phenyl and phenyl-C1-C6-alkyl; wherein the phenyl groups are unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of CN, halogen, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy.


According to still another embodiment of formula I, R5 is in each case independently selected from H, CH(═O), C(═O)C1-C6-alkyl, wherein the acyclic moieties of R5 are unsubstituted or substituted with identical or different groups R5a as defined and preferably defined herein, and wherein the cycloalkyl moieties of R5 are unsubstituted or substituted with identical or different groups R5b as defined and preferably defined herein.


According to one embodiment R5a is independently selected from halogen, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C4-halogenalkoxy. Specifically, R5a is independently selected from F, Cl, Br, I, C1-C2-alkoxy, cyclopropyl, 1-F-cyclopropyl, 1-Cl-cyclopropyl, 1,1-F2-cyclopropyl, 1,1-Cl2-cyclopropyl and C1-C2-halogenalkoxy.


According to still another embodiment of formula I, R5a is independently halogen, in particular selected from F, Cl, Br and I, more specifically F, Cl and Br.


R5b are the possible substituents for the cycloalkyl, heteroaryl and phenyl moieties of R5. R5b according to the invention is independently selected from halogen, OH, ON, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy and C1-C6-alkylthio.


According to one embodiment thereof R5b is independently selected from halogen, CN, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl and C1-C4-halogenalkoxy, in particular halogen, C1-C4-alkyl and C1-C4-alkoxy. Specifically, R5b is independently selected from F, Cl, N, CH3, CHF2, CF3OCH3 and halogenmethoxy.


Particularly preferred embodiments of R5 according to the invention are in Table P5 below, wherein each line of lines P5-1 to P5-32 corresponds to one particular embodiment of the invention, wherein P5-1 to P5-32 are also in any combination with one another a preferred embodiment of the present invention. The connection point to the carbon atom, to which R5 is bound is marked with “#” in the drawings.












TABLE P5







No.
R5









P5-1
H



P5-2
CH3



P5-3
CH2F



P5-4
CHF2



P5-5
CF3



P5-6
C2H5



P5-7
C3H7



P5-8
CH(CH3)2



P5-9
CH2CH2CH3



P5-10
CH2CH2CH2CH3



P5-11
CH2CH(CH3)2



P5-12
C(CH3)3



P5-13
CH2CH2CH2CH2CH3



P5-14
CH═CH2



P5-15
CH2CH═CH2



P5-16
C≡CH



P5-17
CH2C≡CH



P5-18
CH2CH2CH(CH3)2



P5-19
OH



P5-20
OCH3



P5-21
OCHF2



P5-22
OC2H5



P5-23
OCH2OCH3



P5-24
OCH2Ph



P5-25
OCH2CH═CH2



P5-26
C(O)CH3







P5-27


embedded image









P5-28


embedded image









P5-29


embedded image









P5-30


embedded image









P5-31


embedded image









P5-32


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R6 is independently selected from H, halogen, OH, CN, NO2, SH, C1-C6-alkylthio, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C1-C6-alkoxy, C1-C6-halogenalkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, aryloxy, heteroaryloxy, arylamino, heteroarylamino, arylthio, heteroarylthio, CH(═O), C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), C(═O)NH(C1-C6-alkyl), C(═O)N(C1-C6-alkyl)2, CR′═NOR″, a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight, nine-, or ten-membered carbocycle or heterocycle, a five- or six-membered heteroaryl or aryl;


wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(═O) and C(═S), and wherein the heterocycle and heteroaryl contain independently one, two, three or four heteroatoms selected from N, O and S; and wherein R′ and R″ are independently selected from H, C1-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl or aryl; wherein the heterocycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S, and wherein R′ and R″ are independently unsubstituted or substituted with R′″ which is independently selected from halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NHSO2—Rx, C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C1-C6-alkoxy, C1-C6-halogenalkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and phenyl;


wherein Rx is as defined above;


wherein the acyclic moieties of R6 are independently not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R6a, which independently of one another are selected from:


R6a halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkoxy, C1-C4-halogenalkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C6-alkylthio, C1-C6-halogenalkylthio, S(O)n—C1-C6-alkyl, S(O)n-aryl, CH(═O), C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), C(═O)NH(C1-C6-alkyl), C(═O)N(C1-C6-alkyl)2, CR′═NOR″, a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- or heterocycle, a five-, six- or ten-membered heteroaryl, aryl or phenoxy, wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(═O) and C(═S), and wherein the heterocycle and heteroaryl contains independently one, two, three or four heteroatoms selected from N, O and S; wherein the carbo-, heterocyclic, heteroaryl and phenyl groups are independently unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkylthio, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, and S(O)n—C1-C6-alkyl; and wherein Rx, R′ and R″ are as defined above; n is 0, 1, 2; and


wherein the carbo-, heterocyclic, heteroaryl and aryl moieties of R6 are independently unsubstituted or substituted with identical or different groups R6b, which independently of one another are selected from:


R6b halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy, C1-C6-alkylthio, C1-C6-halogenalkylthio, S(O)n—C1-C6-alkyl, C1-C4-alkoxy-C1-C4-alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy; and wherein Rx and n are as defined above.


According to one embodiment of formula I, R6 is independently selected from H, halogen, OH, CN, NO2, SH, C1-C6-alkylthio, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH—SO2—Rx, substituted C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C1-C6-alkoxy, C1-C6-halogenalkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, CH(═O), C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), C(═O)NH(C1-C6-alkyl), C(═O)N(C1-C6-alkyl)2, CR′═NOR″, a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, a five- or six-membered heteroaryl or aryl; wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(═O) and C(═S), and wherein the heterocycle and the heteroaryl contain independently one, two, three or four heteroatoms selected from N, O and S; and wherein R′ and R″ are independently selected from H, C1-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl or aryl; wherein the heterocycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S, and wherein R′ and R″ are independently unsubstituted or substituted by R′″ which is independently selected from halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C1-C6-alkoxy, C1-C6-halogenalkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and phenyl; or


wherein the aliphatic moieties of R6 are independently not further substituted or carry 1, 2, 3 or up to the maximum possible number of identical or different groups R6a, respectively, which independently of one another are selected from:

  • R6a halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH-aryl, N(aryl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, C1-C6-alkoxy, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy, C1-C6-alkylthio, C1-C6-halogenalkylthio, S(O)n—C1-C6-alkyl, S(O)n-aryl, CH(═O), C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), C(═O)NH(C1-C6-alkyl), C(═O)N(C1-C6-alkyl)2, CR′═NOR″, a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, aryl, phenoxy, a five-, six- or ten-membered heteroaryl; wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(═O) and C(═S), five- or six-membered heteroaryl and aryl; wherein the heterocycle and the heteroaryl contain independently 1, 2, 3 or 4 heteroatoms selected from N, O and S; wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(═O) and C(═S); wherein the carbocyclic, heterocyclic, aryl and phenyl groups are independently unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkylthio, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, and S(O)n—C1-C6-alkyl; and wherein Rx, R′, R″ and R″ are as defined above
    • wherein the carbocyclic, heterocyclic, heteroaryl and aryl moieties of R6 are independently not further substituted or carry 1, 2, 3, 4, 5 or up to the maximum number of identical or different groups R6b, respectively, which independently of one another are selected from:
  • R6b halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy, C1-C6-alkylthio, C1-C6-halogenalkylthio, S(O)n—C1-C6-alkyl, C1-C4-alkoxy-C1-C4-alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or substituted with substituents selected from the group consisting of halogen, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy.


According to one embodiment of formula I, R6 is selected from substituted H, C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C3-C6-cycloalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkynyl, C1-C6-alkoxy, aryloxy, heteroaryloxy, arylamino, heteroarylamino, arylthio, heteroarylthio, CN, CH(═O), C(═O)C2-C6-alkyl, C(═O)O(C2-C6-alkyl), CR′═NOR″, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C6-alkyl-five- and six-membered heteroaryl, a five- or six-membered heteroaryl, benzyl, aryl; wherein R′ and R″ are defined below; and wherein the acyclic moieties of R6 are unsubstituted or substituted with identical or different groups R6a as defined below and wherein wherein the carbocycle, heterocycle and heteroaryl and aryl moieties are unsubstituted or substituted with substituents R6b as defined below.


According to one embodiment of formula I, R6 is selected from H, C1-C6-alkyl substituted with halogen, CN, C1-C6-alkoxy, aryloxy, arylamino, arylthio, C1-C4-halogenalkoxy, C1-C6-alkylthio, S(O)n—C1-C6-alkyl, NH—SO2—Rx, N(C1-C6-alkyl)2, NH—SO2—Rx, NH(C1-C6-alkyl), N(C1-C6-alkyl)2, CH(═O), C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), a saturated three-, four-, five-, six-, membered carbo- or heterocycle, aryl, a five- or six-membered heteroaryl; wherein Rx is defined below; and wherein the acyclic moieties of R6 are unsubstituted or substituted with identical or different groups R6a as defined below and wherein wherein the carbocycle, heterocycle and heteroaryl and aryl moieties are unsubstituted or substituted with substituents R6b as defined below.


According to another embodiment of formula I, R6 is H.


According to another embodiment of formula I, R6 is F.


According to another embodiment of formula I, R6 is Cl.


According to another embodiment of formula I, R6 is Br.


According to still another embodiment of formula I, R6 is OH.


According to still another embodiment of formula I, R6 is CN.


According to still another embodiment of formula I, R6 is NO2.


According to still another embodiment of formula I, R6 is SH.


According to still another embodiment of formula I, R6 is C1-C6-alkylthio, such as SCH3, SC2H5, S-n-propyl, S-i-propyl, S-n-butyl, S-i-butyl, S-tert-butyl, S-n-pentyl, S-i-pentyl, CH2SCH3 or CH2SCH2CH3.


According to still another embodiment of formula I, R6 is C1-C6-halogenalkylthio, such as SCF3, SCCl3, CH2SCF3 or CH2SCF3.


According to still another embodiment of formula I, R6 is selected from CN, substituted C1-C6-alkyl, C1-C6-halogenalkyl or C1-C6-alkyl which is substituted, C1-C6-halogenalkyl, phenyl, halogenphenyl and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or is substituted with substituents R6b as defined below. According to one embodiment thereof, the carbocycle is unsubstituted. In a particular embodiment, R6 is selected from C1-C6-halogenalkyl, phenyl-CH2, halogenphenyl-CH2, phenyl, halogenphenyl and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or is substituted with substituents R6b as defined below.


According to still another embodiment of formula I, R6 is selected from H, CN, substituted C1-C6-alkyl, C1-C6-halogenalkyl or C1-C6-alkyl which is substituted, C1-C6-halogenalkyl, phenyl, halogenphenyl, aryloxy, heteroaryloxy, arylamino, heteroarylamino, arylthio, heteroarylthio and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or substituted by substituents R6b as defined below. According to one embodiment thereof, the carbo- and heterocycle is unsubstituted. In a particular embodiment, R6 is selected from substituted C1-C6-halogenalkyl, phenyl, halogenphenyl and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or substituted by substituents R6b as defined below.


According to another embodiment of formula I, R6 is selected from H, CN, substituted C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C6-alkylaryl, aryloxy, arylamino, arylthio, five- or six-membered heteroaryl or aryl which is unsubstituted or substituted with halogen or C1-C6-halogenalkyl, and wherein the acyclic moieties of R6 are unsubstituted or substituted with identical or different groups R6a as defined below and wherein wherein the carbocycle, heterocycle and heteroaryl and aryl moieties are unsubstituted or substituted with substituents R6b as defined below.


According to still another embodiment of formula I, R6 is selected from H, CN, substituted C1-C6-alkyl, C1-C6-halogenalkyl, CN, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C6-alkylaryl, phenyl, pyridine, pyrimidine, thiophene, imidazole, triazol, oxadiazol wherein the acyclic moieties of R6 are unsubstituted or substituted with identical or different groups R6a as defined below and wherein wherein the carbocycle, heterocycle and heteroaryl and aryl moieties are unsubstituted or substituted with substituents R6b as defined below.


According to still another embodiment of formula I, R6 is selected from CN, substituted C1-C6-alkyl, C1-C6-halogenalkyl, CN, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C6-alkylaryl, phenyl, pyridine, pyrimidine, thiophene, imidazole, triazol, oxadiazol wherein the acyclic moieties of R6 are unsubstituted or substituted with identical or different groups R6a as defined below and wherein wherein the carbocycle, heterocycle and heteroaryl and aryl moieties are unsubstituted or substituted with substituents R6b as defined below.


According to still another embodiment of formula I, R6 is C1-C6-alkyl such as CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.


According to still another embodiment of formula I, R6 is C1-C6-alkyl such as CH3.


According to still another embodiment of formula I, R6 is C1-C6-alkyl such as C2H5.


According to still another embodiment of formula I, R6 is C1-C6-alkyl such as CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl which is substituted with at least one group R6a, which independently of one another are selected from:


R6a halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkoxy, C1-C4-halogenalkoxy, C1-C6-alkylthio, C1-C6-halogenalkylthio, S(O)n—C1-C6-alkyl, S(O)n-aryl, CH(═O), C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), C(═O)NH(C1-C6-alkyl), C(═O)N(C1-C6-alkyl)2, CR′═NOR″ a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, five-, six- or ten-membered heteroaryl, aryl or phenoxy, wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(═O) and C(═S), and wherein the heterocycle and heteroaryl contains independently one, two, three or four heteroatoms selected from N, O and S; wherein the carbocyclic, heterocyclic, heteroaryl, aryl groups are independently unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkylthio, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, and S(O)n—C1-C6-alkyl.


According to still another embodiment of formula I, R6 is CH3 is substituted with at least one group R6a, which independently of one another are selected from:


R6a halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH-aryl, N(aryl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkoxy, C1-C4-halogenalkoxy, C1-C6-alkylthio, C1-C6-halogenalkylthio, S(O)n—C1-C6-alkyl, S(O)n-aryl, CH(═O), C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), C(═O)NH(C1-C6-alkyl), C(═O)N(C1-C6-alkyl)2, CR′═NOR″, a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, five-, six- or ten-membered heteroaryl, an aryl or phenoxy, wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(═O) and C(═S), and wherein the heterocycle and heteroaryl contains independently one, two, three or four heteroatoms selected from N, O and S; wherein the carbocyclic, heterocyclic, heteroaryl, heteroaryl and phenyl groups are independently unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkylthio, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, and S(O)n—C1-C6-alkyl.


According to still another embodiment of formula I, R6 is C2H5 is substituted with at least one group R6a, which independently of one another are selected from:


R6a halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH-aryl, N(aryl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkoxy, C1-C4-halogenalkoxy, C1-C6-alkylthio, C1-C6-halogenalkylthio, S(O)n—C1-C6-alkyl, S(O)n-aryl, CH(═O), C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), C(═O)NH(C1-C6-alkyl), C(═O)N(C1-C6-alkyl)2, CR′═NOR″ a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, five-, six- or ten-membered heteroaryl, phenyl or phenoxy; wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(═O) and C(═S), and wherein the heterocycle and heteroaryl contains independently one, two, three or four heteroatoms selected from N, O and S; wherein the carbocyclic, heterocyclic, heteroaryl, aryl and phenyl groups are independently unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkylthio, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, and S(O)n—C1-C6-alkyl.


According to still another embodiment of formula I, R6 is CH2CN.


According to still another embodiment of formula I, R6 is CH2OH.


According to still another embodiment of formula I, R6 is C1-C6-halogenalkyl, in particular C1-C4-halogenalkyl, more specifically C1-C2-halogenalkyl, such as CF3, CCl3, FCH2, ClCH2, F2CH, Cl2CH, CF3CH2, CCl3CH2 or CF2CHF2.


According to still another embodiment of formula I, R6 is CH2F.


According to still another embodiment of formula I, R6 is CHF2.


According to still another embodiment of formula I, R6 is CF3.


According to still a further embodiment of formula I, R6 is C2-C6-alkenyl, in particular C2-C4-alkenyl, such as CH═CH2, CH2CH═CH2 or C(CH3)C═CH2.


According to a further specific embodiment of formula I, R6 is C2-C6-halogenalkenyl, in particular C2-C4-halogenalkenyl, more specifically C2-C3-halogenalkenyl such as CH═CHF, CH═CHCl, CH═CF2, CH═CCl2, CF═CF2, CCl═CCl2, CH2CH═CHF, CH2CH═CHCl, CH2CH═CF2, CH2CH═CCl2, CH2CF═CF2, CH2CCl═CCl2, CF2CF═CF2 or CCl2CCl═CCl2.


According to still a further embodiment of formula I, R6 is C2-C6-cycloalkenyl, in particular C2-C4-cycloalkenyl, such as CH═CH2-cPr.


According to still a further embodiment of formula I, R6 is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as C≡CH, C≡C—Cl, C≡C—CH3, CH2—C≡CH, CH2—C≡CCl or CH2—C≡C—CH3.


According to still a further embodiment of formula I, R6 is C2-C6-cycloalkynyl in particular C2-C4-cycloalkynyl, such as C≡C-cPr.


According to a further specific embodiment of formula I, R6 is C1-C6-alkoxy, in particular C1-C4-alkoxy, more specifically C1-C2-alkoxy such as OCH3, CH2CH3 or CH2OCH3.


According to a further specific embodiment of formula I, R6 is C1-C6-alkyl-C1-C6-alkoxy, in particular C1-C4-alkyl-C1-C4-alkoxy, more specifically C1-C2-alkyl-C1-C2-alkoxy, such as CH2OCH3 or CH2OCH2CH3.


According to a further specific embodiment of formula I, R6 is C2-C6-alkenyloxy, in particular C2-C4-alkenyloxy, more specifically C1-C2-alkenyloxy such as OCH═CH2, OCH2CH═CH2 OC(CH3)CH═CH2, CH2OCH═CH2, or CH2OCH2CH═CH2.


According to a further specific embodiment of formula I, R6 is C2-C6-alkynyloxy, in particular C2-C4-alkynyloxy, more specifically C1-C2-alkynyloxy such as OC≡CH, OCH2C≡CH or CH2OC≡CH


According to a further specific embodiment of formula I, R6 is C1-C6-halogenalkoxy, in particular C1-C4-halogenalkoxy, more specifically C1-C2-halogenalkoxy such as OCF3, OCHF2, OCH2F, OCCl3, OCHCl2 or OCH2Cl, in particular OCF3, OCHF2, OCCl3 or OCHCl2.


According to a further specific embodiment of formula I, R6 is C1-C6-alkyl-C1-C6-halogenalkoxy, in particular C1-C4-alkyl-C1-C4-halogenalkoxy, more specifically C1-C2-alkyl-C1-C2-halogenalkoxy such as CH2OCF3, CH2OCHF2, CH2OCH2F, CH2OCCl3, CH2OCHCl2 or CH2OCH2Cl, in particular CH2OCF3, CH2OCHF2, CH2OCCl3 or CH2OCHCl2.


According to a further specific embodiment of formula I, R6 is CH(═O), C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), C(═O)NH(C1-C6-alkyl) or C(═O)N(C1-C6-alkyl)2, wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.


According to a further specific embodiment of formula I, R6 is C1-C4-alkyl-CH(═O), C1-C4-alkyl-C(═O)C1-C6-alkyl, C1-C4-alkyl-C(═O)O(C1-C6-alkyl), C1-C4-alkyl-C(═O)NH(C1-C6-alkyl) or C1-C4-alkyl-C(═O)N(C1-C6-alkyl)2, especially CH2CH(═O), CH2C(═O)C1-C6-alkyl, CH2C(═O)O(C1-C6-alkyl), CH2C(═O)NH(C1-C6-alkyl) or CH2C(═O)N(C1-C6-alkyl)2 wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.


According to a further specific embodiment of formula I, R6 is CR′═NOR″ such as C(CH3)═NOCH3, C(CH3)═NOCH2CH3 or C(CH3)═NOCF3.


According to a further specific embodiment of formula I, R6 is C1-C6-alkyl-NH(C1-C4-alkyl) or C1-C6-alkyl-N(C1-C4-alkyl)2, wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.


According to a further specific embodiment of formula I, R6 is C1-C6-alkylthio, in particular C1-C4-alkoxy, more specifically C1-C3-alkylthio such as CH2SCH3 or CH2SCH2CH3.


According to a further specific embodiment of formula I, R6 is C1-C6-alkyl-S(O)n—C1-C6-alkyl, wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl and n is 1, 2 or 3.


According to a further specific embodiment of formula I, R6 is C1-C6-alkyl-S(O)n—C1-C6-halogenalkyl, wherein halogenalkyl is CF3 or CHF2 and n is 1, 2 or 3.


According to a further specific embodiment of formula I, R6 is C1-C6-alkyl-S(O)n-aryl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted with identical or different groups R6b which independently of one another are selected from halogen, C1-C2-alkyl, C1-C2-alkoxy, C1-C2-halogenalkyl, C1-C2-halogenalkoxy and S(O)n—C1-C6-alkyl, in particular F, Cl, Br, CH3, OCH3, CF3, CHF2, OCHF2, OCF3. According to one embodiment, R6 is unsubstituted phenyl. According to another embodiment, R6 is phenyl, that is substituted with one, two or three, in particular one, halogen, in particular selected from F, Cl and Br, more specifically selected from F and Cl.


According to a further specific embodiment of formula I, R1 is C1-C6-alkyl-NH—SO2—Rx wherein Rx is C1-C4-alkyl, C1-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted with one, two, three, four or five substituents Rx2 independently selected from C1-C4-alkyl, halogen, OH, CN, C1-C4-halogenalkyl, C1-C4-alkoxy, or C1-C4-halogenalkoxy, such as CH2NHSO2CF3 or CH2NHSO2OCH3.


According to still another embodiment of formula I, R6 is selected from C1-C6-alkyl which is substituted, a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle, in particular three-, four-, five- or six-membered, wherein the carbocycle is unsubstituted or substituted with substituents R6b as defined below. According to one embodiment thereof, the carbocycle is unsubstituted.


According to one embodiment, R6 is selected from C1-C6-alkyl, especially CH2 which is substituted with a 3-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R6b. According to still another embodiment of formula I, it is substituted with R6b.


According to one embodiment, R6 is selected from C1-C6-alkyl, especially CH2 which is substituted with a 4-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R6b. According to still another embodiment of formula I, it is substituted with R6b.


According to one embodiment, R6 is selected from C1-C6-alkyl, especially CH2 which is substituted with a 5-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R6b. According to still another embodiment of formula I, it is substituted with R6b.


According to one embodiment, R6 is selected from C1-C6-alkyl, especially CH2 which is substituted with a 6-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R6b. According to still another embodiment of formula I, it is substituted with R6b.


According to a further specific embodiment of formula I, R6 is C1-C6-alkylheterocycle, especially CH2 substituted with a 4-membered saturated heterocycle which contains 1 or 2 heteroatoms, in particular 1 heteroatom, from the group consisting of N, O and S, as ring members. According to one embodiment, the heterocycle contains one O as heteroatom. For example, the formed heterocycle is oxetane. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R6b. According to still another embodiment of formula I, it is substituted with R6b.


According to a further specific embodiment of formula I, R6 is C1-C6-alkylheterocycle, especially CH2 substituted with a 5-membered saturated heterocycle which contains 1, 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S, as ring members. According to one embodiment, the heterocycle contains one O as heteroatom. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R6b. According to still another embodiment of formula I, it is substituted with R6b.


According to a further specific embodiment of formula I, R6 is C1-C6-alkylheterocycle, especially CH2 substituted by a 6-membered saturated heterocycle which contains 1, 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R6b.


According to still another embodiment of formula I, it is substituted with R6b. According to one specific embodiment thereof, said 6-membered saturated heterocycle contains 1 or 2, in particular 1, heteroatom(s) O. According to one embodiment thereof, the respective 6-membered heterocycle is unsubstituted, i.e. it does not carry any substituent R6b. According to still another embodiment of formula I, it is substituted with R6b.


According to a further specific embodiment of formula I, R6 is C1-C6-alkylheterocycle, especially CH2 substituted with a 5-membered saturated heterocycle which contains one N as ring member and optionally one or two groups CH2 are replaced by C(═O).


According to still another embodiment of formula I, R6 is a partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle, in particular three-, four-, five- or six-membered, wherein the carbocycle is unsubstituted or substituted with substituents R6b as defined below. According to one embodiment thereof, the carbocycle is unsubstituted.


According to still another embodiment of formula I, R6 is a partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the carbocycle and heterocycle are unsubstituted or substituted with substituents R6b as defined below. According to one embodiment thereof, the carbocycle or heterocycle is unsubstituted.


According to still a further embodiment, R6 is a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the carbocycle and heterocycle are unsubstituted or substituted with substituents R6b as defined below. According to one embodiment thereof, the carbocycle or heterocycle is unsubstituted.


According to still another embodiment of formula I, R6 is a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle, in particular three-, four-, five- or six-membered, wherein the carbocycle is unsubstituted or substituted with substituents R6b as defined below. According to one embodiment thereof, the carbocycle is unsubstituted.


According to one embodiment, R6 is a 3-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R6b. According to still another embodiment of formula I, it is substituted with R6b.


According to one embodiment, R6 is a 3-membered saturated carbocycle, which is unsubstituted such as cyclopropyl.


According to one embodiment, R6 is a 3-membered saturated carbocycle, which is substituted with halogen, more specifically by F, such as C3H3F2.


According to one embodiment, R6 is a 3-membered saturated carbocycle, which is substituted with halogen. More specifically by Cl, such as C3H3Cl2.


According to one embodiment, R6 is a 4-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R6b. According to still another embodiment of formula I, it is substituted with R6b.


According to one embodiment, R6 is a 5-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R6b. According to still another embodiment of formula I, it is substituted with R6b.


According to one embodiment, R6 is a 6-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R6b. According to still another embodiment of formula I, it is substituted with R6b.


According to still another embodiment of formula I, R6 is a partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the heterocycle is unsubstituted or substituted with substituents R6b as defined below. According to one embodiment thereof, the heterocycle is unsubstituted.


According to still another embodiment of formula I, R6 is a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the heterocycle is unsubstituted or substituted with substituents R6b as defined below. According to one embodiment thereof, the heterocycle is unsubstituted.


According to still another embodiment of formula I, in the embodiments of R6 described above, the heterocycle contains preferably one, two or three, more specifically one or two heteroatoms selected from N, O and S. More specifically, the heterocycle contains one heteroatom selected from N, O and S. In particular, the heterocycle contains one or two, in particular one O.


According to one embodiment, R6 is a 4-membered saturated heterocycle which contains 1 or 2 heteroatoms, in particular 1 heteroatom, from the group consisting of N, O and S, as ring members. According to one embodiment, the heterocycle contains one O as heteroatom. For example, the formed heterocycle is oxetane. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R6b. According to still another embodiment of formula I, it is substituted with R6b.


According to still another embodiment of formula I, R6 is a 5-membered saturated heterocycle which contains 1, 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S, as ring members. According to one embodiment, the heterocycle contains one O as heteroatom. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R6b. According to still another embodiment of formula I, it is substituted with R6b.


According to still another embodiment of formula I, R6 is a 6-membered saturated heterocycle which contains 1, 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R6b. According to still another embodiment of formula I, it is substituted with R6b. According to one specific embodiment thereof, said 6-membered saturated heterocycle contains 1 or 2, in particular 1, heteroatom(s) O. According to one embodiment thereof, the respective 6-membered heterocycle is unsubstituted, i.e. it does not carry any substituent R6b. According to still another embodiment of formula I, it is substituted with R6b.


According to still another embodiment of formula I, R6 is phenyl-C1-C6-alkyl, such as phenyl-CH2, wherein the phenyl moiety in each case is unsubstituted or substituted with one, two or three identical or different groups R6b which independently of one another are selected from CN, halogen, C1-C2-alkyl, C1-C2-alkoxy, C1-C2-halogenalkyl, C1-C2-halogenalkoxy and S(O)n—C1-C6-alkyl, in particular from CN, F, Cl, Br, CH3, OCH3O CF3. CHF2, OCHF2, OCF3 and S(O)2CH3.


According to still another embodiment of formula I, R6 is aryl, in particular phenyl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted with identical or different groups R6b which independently of one another are selected from CN, halogen, C1-C2-alkyl, C1-C2-alkoxy, C1-C2-halogenalkyl, C1-C2-halogenalkoxy and S(O)n—C1-C6-alkyl, in particular from CN, F, Cl, Br, CH3, OCH3, CF3, CHF2, OCHF2, OCF3. According to one embodiment, R6 is unsubstituted phenyl. According to another embodiment, R6 is phenyl, that is substituted with one, two or three, in particular one, halogen, in particular selected from F, Cl and Br, more specifically selected from F and Cl.


According to still another embodiment of formula I, R6 is a 5-membered heteroaryl such as pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,2,4-triazolyl-1-yl, 1,2,4-triazol-3-yl 1,2,4-triazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl and 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl.


According to still another embodiment of formula I, R6 is a 6-membered heteroaryl, such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl and 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl.


According to a further specific embodiment of formula I, R6 is C1-C6-alkyl, especially CH2 substituted by a 5-membered saturated heteroaryl which contains 1, 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R6b. According to still another embodiment of formula I, it is substituted by R6b.


According to a further specific embodiment of formula I, R6 is C1-C6-alkyl, especially CH2 substituted by a 5-membered saturated heteroaryl which contains one N as ring member. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R6b. According to still another embodiment of formula I, it is substituted by R6b.


According to a further specific embodiment of formula I, R6 is C1-C6-alkyl, especially CH2 substituted by a 5-membered saturated heteroaryl which contains two N as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R6b. According to still another embodiment of formula I, it is substituted by R6b.


According to a further specific embodiment of formula I, R6 is C1-C6-alkyl, especially CH2 substituted by a 5-membered saturated heteroaryl which contains three N as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R6b. According to still another embodiment of formula I, it is substituted by R6b. According to one specific embodiment thereof, said 5-membered saturated heterocycle contains 1 or 2, in particular 1, heteroatom(s) O.


According to a further specific embodiment of formula I, R6 is C1-C6-alkyl, especially CH2 substituted by a 5-membered saturated heteroaryl which contains one S as ring member. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R6b. According to still another embodiment of formula I, it is substituted by R6b.


According to a further specific embodiment of formula I, R6 is C1-C6-alkyl, especially CH2 substituted by a 5-membered saturated heteroaryl which contains one S and one N as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R6b. According to still another embodiment of formula I, it is substituted by R6b.


According to a further specific embodiment of formula I, R6 is C1-C6-alkyl, especially CH2 substituted by a 5-membered saturated heteroaryl which contains one S and two N as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R6b. According to still another embodiment of formula I, it is substituted by R6b.


According to a further specific embodiment of formula I, R6 is C1-C6-alkyl, especially CH2 substituted by a 5-membered saturated heteroaryl which contains one oxygen and one N as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R6b. According to still another embodiment of formula I, it is substituted by R6b.


According to a further specific embodiment of formula I, R6 is C1-C6-alkyl, especially CH2 substituted by a 5-membered saturated heteroaryl which contains one oxygen and two N as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R6b. According to still another embodiment of formula I, it is substituted by R6b.


According to a further specific embodiment of formula I, R6 is C1-C6-alkyl, especially CH2 substituted by a 6-membered saturated heteroaryl which contains 1, 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R6b. According to still another embodiment of formula I, it is substituted by R6b.


According to a further specific embodiment of formula I, R6 is C1-C6-alkyl, especially CH2 substituted by a 6-membered saturated heteroaryl which one N as ring member. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R6b. According to still another embodiment of formula I, it is substituted by R6b.


According to a further specific embodiment of formula I, R6 is C1-C6-alkyl, especially CH2 substituted by a 6-membered saturated heteroaryl which two N as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R6b. According to still another embodiment of formula I, it is substituted by R6b.


According to a further specific embodiment of formula I, R6 is C1-C6-alkyl, especially CH2 substituted by a 10-membered saturated heteroaryl which contains 1, 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R6b. According to still another embodiment of formula I, it is substituted by R6b. According to one specific embodiment thereof, said 10-membered saturated heterocycle contains 1 or 2, in particular 1, heteroatom(s) N.


According to a further specific embodiment of formula I, R6 is C1-C6-alkyl, especially CH2 substituted by a 10-membered saturated heteroaryl which one N as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R6b. According to still another embodiment of formula I, it is substituted by R6b.


According to still another embodiment of formula I, R6 is CH2 substituted by a 5-membered heteroaryl such as pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,2,4-triazolyl-1-yl, 1,2,4-triazol-3-yl 1,2,4-triazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl and 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl.


According to still another embodiment of formula I, R6 is CH2 substituted by a 6-membered heteroaryl, such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl and 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl.


According to a further particular embodiment, R6 is selected from C1-C6-alkyl, C1-C6-halogenalkyl, CN, C2-C6-alkenyl, C2-C6-halogenalkenyl, C3-C6-cycloalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C1-C6-alkoxy, C3-C6-cycloalkynyl, C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), CR′═NOR″, C3-C6-halogencycloalkyl a saturated three-, four-, five-, six-, membered carbocycle or heterocycle, a five- or six-membered heteroaryl or aryl; and C1-C6-alkyl substituted by CN, C1-C6-alkoxy, C1-C4-halogenalkoxy, C1-C6-alkylthio, S(O)n—C1-C6-alkyl, NH—SO2—Rx, NH(C1-C6-alkyl), N(C1-C6-alkyl)2, C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), a saturated three-, four-, five-, six-, membered carbocycle, heterocycle, aryl or heteroaryl; wherein the carbocycle, heterocycle, aryl and heteroaryl is unsubstituted or carries one, two, three or four substituents R6b as defined below. According to one embodiment thereof, the carbocycle, heterocycle, heteroaryl and aryl are unsubstituted. In a particular embodiment, R6 is selected from CN, C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C1-C6-alkoxy, a saturated three-, four-, five-, six-, membered carbocycle or heterocycle, a five- or six-membered heteroaryl or aryl; and C1-C6-alkyl substituted by a saturated three-, four-, five-, six-, membered carbocycle, heterocycle, aryl or heteroaryl; wherein the carbocycle, heterocycle, aryl and heteroaryl are unsubstituted or carries one, two, three or four substituents R6b as defined below.


According to a further particular embodiment, R6 is selected from C1-C6-halogenalkyl, CN, C2-C6-alkenyl, C2-C6-halogenalkenyl, C3-C6-cycloalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C1-C6-alkoxy, C3-C6-cycloalkynyl, C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), CR′═NOR″, C3-C6-halogencycloalkyl a saturated three-, four-, five-, six-, membered carbocycle or heterocycle, a five- or six-membered heteroaryl or aryl; and C1-C6-alkyl substituted by CN, C1-C6-alkoxy, C1-C4-halogenalkoxy, C1-C6-alkylthio, S(O)n—C1-C6-alkyl, NH—SO2—Rx, NH(C1-C6-alkyl), N(C1-C6-alkyl)2, C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), a saturated three-, four-, five-, six-, membered carbocycle, heterocycle, aryl or heteroaryl; wherein the carbocycle, heterocycle, aryl and heteroaryl is unsubstituted or carries one, two, three or four substituents R6b as defined below. According to one embodiment thereof, the carbocycle, heterocycle, heteroaryl and aryl are unsubstituted. In a particular embodiment, R6 is selected from CN, C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C1-C6-alkoxy, a saturated three-, four-, five-, six-, membered carbocycle or heterocycle, a five- or six-membered heteroaryl or aryl; and C1-C6-alkyl substituted by a saturated three-, four-, five-, six-, membered carbocycle, heterocycle, aryl or heteroaryl; wherein the carbocycle, heterocycle, aryl and heteroaryl are unsubstituted or carries one, two, three or four substituents R6b as defined below.


Particularly preferred embodiments of R6 according to the invention are in Table P6 below, wherein each line of lines P6-1 to P6-209 corresponds to one particular embodiment of the invention, wherein P6-1 to P6-209 are also in any combination with one another a preferred embodiment of the present invention. The connection point to the carbon atom, to which R6 is bound is marked with “#” in the drawings.









TABLE P6







(py = pyridyl)










No.
R6







P6-1
CH3



P6-2
CH2CH3



P6-3
CF3



P6-4
CH2F



P6-5
CH2Cl



P6-6
CHF2



P6-7
CHCl2



P6-8
CH2CF3



P6-9
CH2CCl3



P6-10
CF2CHF2



P6-11
CH2OCH3



P6-12
CH2OCH2F



P6-13
CH2OCHF2



P6-14
CH2OCF3



P6-15
CH2OCF2CHF2



P6-16
CH2NHMe



P6-17
CH2SMe



P6-18
CH2SOMe



P6-19
CH2SO2Me



P6-20
CH2NMe2



P6-21
CH2NSO2CF3



P6-22
CH2NSO2CH3



P6-23
CN



P6-24
CH2CN



P6-25
CHO



P6-26
COMe



P6-27
CO2Me



P6-28
CH2CHO



P6-29
CH2COMe



P6-30
CH2CO2Me







P6-31


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P6-32


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P6-33


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P6-34


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P6-35


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P6-36


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P6-37


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P6-38


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P6-39


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P6-40


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P6-41


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P6-42


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P6-43


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P6-44


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P6-45


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P6-46


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P6-47


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P6-48


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P6-49


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P6-50


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P6-51


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P6-52


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P6-53


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C6H5



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3-Cl—C6H4



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2-Cl—C6H4



P6-67
2,4-Cl2—C6H3



P6-68
4-F—C6H4



P6-69
3-F—C6H4



P6-70
2-F—C6H4



P6-71
2,4-F2—C6H3



P6-72
4-MeO—C6H4



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3-MeO—C6H4



P6-74
2-MeO—C6H4



P6-75
4-MeO2S—C6H4



P6-76
3-MeO2S—C6H4



P6-77
2-MeO2S—C6H4



P6-78
—CH2—C6H5



P6-79
—CH2—C6H4—4-F



P6-80
—CH2—C6H4—4-Cl



P6-81
—CH2—C6H3—2,4-Cl2



P6-82
—CH2—C6H4—4-SO2Me



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3-py



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CH(CH3)CH2CH3



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CH2CH(CH3)CH3



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C(CH3)3



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—O—C6H4—3-F



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—O—C6H4—4-F



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—O—C6H4—2-Cl



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R7 is independently selected from halogen, OH, CN, NO2, SH, C1-C6-alkylthio, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C1-C6-alkoxy, C1-C6-halogenalkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, aryloxy, heteroaryloxy, arylamino, heteroarylamino, arylthio, heteroarylthio, CH(═O), C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), C(═O)NH(C1-C6-alkyl), C(═O)N(C1-C6-alkyl)2, CR′═NOR″, a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight, nine-, or ten-membered carbocycle or heterocycle, a five- or six-membered heteroaryl or aryl; wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(═O) and C(═S), and wherein the heterocycle and heteroaryl contain independently one, two, three or four heteroatoms selected from N, O and S; and wherein R′ and R″ are independently selected from H, C1-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl or aryl; wherein the heterocycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S, and wherein R′ and R″ are independently unsubstituted or substituted with R′″ which is independently selected from halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NHSO2—Rx, C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C1-C6-alkoxy, C1-C6-halogenalkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and phenyl;


wherein Rx is as defined above;


wherein the acyclic moieties of R7 are independently not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R7a, which independently of one another are selected from:


R7a halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkoxy, C1-C4-halogenalkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C6-alkylthio, C1-C6-halogenalkylthio, S(O)n—C1-C6-alkyl, S(O)n-aryl, CH(═O), C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), C(═O)NH(C1-C6-alkyl), C(═O)N(C1-C6-alkyl)2, CR′═NOR″, a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- or heterocycle, a five-, six- or ten-membered heteroaryl, aryl or phenoxy, wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(═O) and C(═S), and wherein the heterocycle and heteroaryl contains independently one, two, three or four heteroatoms selected from N, O and S; wherein the carbo-, heterocyclic, heteroaryl and phenyl groups are independently unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkylthio, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, and S(O)n—C1-C6-alkyl; and wherein Rx, R′ and R″ are as defined above; n is 0, 1, 2; and


wherein the carbo-, heterocyclic, heteroaryl and aryl moieties of R7 are independently unsubstituted or substituted with identical or different groups R7b, which independently of one another are selected from:


R7b halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy, C1-C6-alkylthio, C1-C6-halogenalkylthio, S(O)n—C1-C6-alkyl, C1-C4-alkoxy-C1-C4-alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy; and wherein Rx and n are as defined above.


According to one embodiment of formula I, R7 is independently selected from halogen, OH, CN, NO2, SH, C1-C6-alkylthio, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH—SO2—Rx, substituted C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C1-C6-alkoxy, C1-C6-halogenalkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, CH(═O), C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), C(═O)NH(C1-C6-alkyl), C(═O)N(C1-C6-alkyl)2, CR′═NOR″, a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, a five- or six-membered heteroaryl or aryl; wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(═O) and C(═S), and wherein the heterocycle and the heteroaryl contain independently one, two, three or four heteroatoms selected from N, O and S; and wherein R′ and R″ are independently selected from H, C1-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl or aryl; wherein the heterocycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S, and wherein R′ and R″ are independently unsubstituted or substituted by R′″ which is independently selected from halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C1-C6-alkoxy, C1-C6-halogenalkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and phenyl; or


wherein the aliphatic moieties of R7 are independently not further substituted or carry 1, 2, 3 or up to the maximum possible number of identical or different groups R7a, respectively, which independently of one another are selected from:

  • R7a halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH-aryl, N(aryl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, C1-C6-alkoxy, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy, C1-C6-alkylthio, C1-C6-halogenalkylthio, S(O)n—C1-C6-alkyl, S(O)n-aryl, CH(═O), C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), C(═O)NH(C1-C6-alkyl), C(═O)N(C1-C6-alkyl)2, CR′═NOR″, a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, aryl, phenoxy, a five-, six- or ten-membered heteroaryl; wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(═O) and C(═S), five- or six-membered heteroaryl and aryl; wherein the heterocycle and the heteroaryl contain independently 1, 2, 3 or 4 heteroatoms selected from N, O and S; wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(═O) and C(═S); wherein the carbocyclic, heterocyclic, aryl and phenyl groups are independently unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkylthio, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, and S(O)n—C1-C6-alkyl; and wherein Rx, R′, R″ and R″ are as defined above
    • wherein the carbocyclic, heterocyclic, heteroaryl and aryl moieties of R7 are independently not further substituted or carry 1, 2, 3, 4, 5 or up to the maximum number of identical or different groups R7b, respectively, which independently of one another are selected from:
  • R7b halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy, C1-C6-alkylthio, C1-C6-halogenalkylthio, S(O)n—C1-C6-alkyl, C1-C4-alkoxy-C1-C4-alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or substituted with substituents selected from the group consisting of halogen, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy.


According to one embodiment of formula I, R7 is selected from substituted C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C3-C6-cycloalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkynyl, C1-C6-alkoxy, aryloxy, heteroaryloxy, arylamino, heteroarylamino, arylthio, heteroarylthio, CN, CH(═O), C(═O)C2-C6-alkyl, C(═O)O(C2-C6-alkyl), CR′═NOR″, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C6-alkyl-five- and six-membered heteroaryl, a five- or six-membered heteroaryl, benzyl, aryl; wherein R′ and R″ are defined below; and wherein the acyclic moieties of R7 are unsubstituted or substituted with identical or different groups R7a as defined below and wherein wherein the carbocycle, heterocycle and heteroaryl and aryl moieties are unsubstituted or substituted with substituents R7b as defined below.


According to one embodiment of formula I, R7 is selected from C1-C6-alkyl substituted with halogen, CN, C1-C6-alkoxy, aryloxy, arylamino, arylthio, C1-C4-halogenalkoxy, C1-C6-alkylthio, S(O)n—C1-C6-alkyl, NH—SO2—Rx, N(C1-C6-alkyl)2, NH—SO2—Rx, NH(C1-C6-alkyl), N(C1-C6-alkyl)2, CH(═O), C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), a saturated three-, four-, five-, six-, membered carbo- or heterocycle, aryl, a five- or six-membered heteroaryl; wherein Rx is defined below; and wherein the acyclic moieties of R7 are unsubstituted or substituted with identical or different groups R7a as defined below and wherein wherein the carbocycle, heterocycle and heteroaryl and aryl moieties are unsubstituted or substituted with substituents R7b as defined below.


According to another embodiment of formula I, R7 is F.


According to another embodiment of formula I, R7 is Cl.


According to another embodiment of formula I, R7 is Br.


According to still another embodiment of formula I, R7 is OH.


According to still another embodiment of formula I, R7 is CN.


According to still another embodiment of formula I, R7 is NO2.


According to still another embodiment of formula I, R7 is SH.


According to still another embodiment of formula I, R7 is C1-C6-alkylthio, such as SCH3, SC2H5, S-n-propyl, S-i-propyl, S-n-butyl, S-i-butyl, S-tert-butyl, S-n-pentyl, S-i-pentyl, CH2SCH3 or CH2SCH2CH3.


According to still another embodiment of formula I, R7 is C1-C6-halogenalkylthio, such as SCF3, SCCl3, CH2SCF3 or CH2SCF3.


According to still another embodiment of formula I, R7 is selected from CN, substituted C1-C6-alkyl, C1-C6-halogenalkyl or C1-C6-alkyl which is substituted, C1-C6-halogenalkyl, phenyl, halogenphenyl and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or is substituted with substituents R7b as defined below. According to one embodiment thereof, the carbocycle is unsubstituted. In a particular embodiment, R7 is selected from C1-C6-halogenalkyl, phenyl-CH2, halogenphenyl-CH2, phenyl, halogenphenyl and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or is substituted with substituents R7b as defined below.


According to still another embodiment of formula I, R7 is selected from CN, substituted C1-C6-alkyl, C1-C6-halogenalkyl or C1-C6-alkyl which is substituted, C1-C6-halogenalkyl, phenyl, halogenphenyl, aryloxy, heteroaryloxy, arylamino, heteroarylamino, arylthio, heteroarylthio and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or substituted by substituents R7b as defined below. According to one embodiment thereof, the carbo- and heterocycle is unsubstituted. In a particular embodiment, R7 is selected from substituted C1-C6-halogenalkyl, phenyl, halogenphenyl and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or substituted by substituents R7b as defined below.


According to another embodiment of formula I, R7 is selected from CN, substituted C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C6-alkylaryl, aryloxy, arylamino, arylthio, five- or six-membered heteroaryl or aryl which is unsubstituted or substituted with halogen or C1-C6-halogenalkyl, and wherein the acyclic moieties of R7 are unsubstituted or substituted with identical or different groups R7a as defined below and wherein wherein the carbocycle, heterocycle and heteroaryl and aryl moieties are unsubstituted or substituted with substituents R7b as defined below.


According to still another embodiment of formula I, R7 is selected from CN, substituted C1-C6-alkyl, C1-C6-halogenalkyl, CN, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C6-alkylaryl, phenyl, pyridine, pyrimidine, thiophene, imidazole, triazol, oxadiazol wherein the acyclic moieties of R7 are unsubstituted or substituted with identical or different groups R7a as defined below and wherein wherein the carbocycle, heterocycle and heteroaryl and aryl moieties are unsubstituted or substituted with substituents R7b as defined below.


According to still another embodiment of formula I, R7 is C1-C6-alkyl such as CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.


According to still another embodiment of formula I, R7 is C1-C6-alkyl such as CH3.


According to still another embodiment of formula I, R7 is C1-C6-alkyl such as C2H5.


According to still another embodiment of formula I, R7 is C1-C6-alkyl such as CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl which is substituted with at least one group R7a, which independently of one another are selected from:


R7a halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkoxy, C1-C4-halogenalkoxy, C1-C6-alkylthio, C1-C6-halogenalkylthio, S(O)n—C1-C6-alkyl, S(O)n-aryl, CH(═O), C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), C(═O)NH(C1-C6-alkyl), C(═O)N(C1-C6-alkyl)2, CR′═NOR″ a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, five-, six- or ten-membered heteroaryl, aryl or phenoxy, wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(═O) and C(═S), and wherein the heterocycle and heteroaryl contains independently one, two, three or four heteroatoms selected from N, O and S; wherein the carbocyclic, heterocyclic, heteroaryl, aryl groups are independently unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkylthio, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, and S(O)n—C1-C6-alkyl.


According to still another embodiment of formula I, R7 is CH3 is substituted with at least one group R7a, which independently of one another are selected from:


R7a halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH-aryl, N(aryl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkoxy, C1-C4-halogenalkoxy, C1-C6-alkylthio, C1-C6-halogenalkylthio, S(O)n—C1-C6-alkyl, S(O)n-aryl, CH(═O), C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), C(═O)NH(C1-C6-alkyl), C(═O)N(C1-C6-alkyl)2, CR′═NOR″, a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, five-, six- or ten-membered heteroaryl, an aryl or phenoxy, wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(═O) and C(═S), and wherein the heterocycle and heteroaryl contains independently one, two, three or four heteroatoms selected from N, O and S; wherein the carbocyclic, heterocyclic, heteroaryl, heteroaryl and phenyl groups are independently unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkylthio, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, and S(O)n—C1-C6-alkyl.


According to still another embodiment of formula I, R7 is C2H5 is substituted with at least one group R7a, which independently of one another are selected from:


R7a halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH-aryl, N(aryl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkoxy, C1-C4-halogenalkoxy, C1-C6-alkylthio, C1-C6-halogenalkylthio, S(O)n—C1-C6-alkyl, S(O)n-aryl, CH(═O), C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), C(═O)NH(C1-C6-alkyl), C(═O)N(C1-C6-alkyl)2, CR′═NOR″ a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, five-, six- or ten-membered heteroaryl, phenyl or phenoxy; wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(═O) and C(═S), and wherein the heterocycle and heteroaryl contains independently one, two, three or four heteroatoms selected from N, O and S; wherein the carbocyclic, heterocyclic, heteroaryl, aryl and phenyl groups are independently unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkylthio, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, and S(O)n—C1-C6-alkyl.


According to still another embodiment of formula I, R7 is CH2CN.


According to still another embodiment of formula I, R7 is CH2OH.


According to still another embodiment of formula I, R7 is C1-C6-halogenalkyl, in particular C1-C4-halogenalkyl, more specifically C1-C2-halogenalkyl, such as CF3, CCl3, FCH2, ClCH2, F2CH, Cl2CH, CF3CH2, CCl3CH2 or CF2CHF2.


According to still another embodiment of formula I, R7 is CH2F.


According to still another embodiment of formula I, R7 is CHF2.


According to still another embodiment of formula I, R7 is CF3.


According to still a further embodiment of formula I, R7 is C2-C6-alkenyl, in particular C2-C4-alkenyl, such as CH═CH2, CH2CH═CH2 or C(CH3)C═CH2.


According to a further specific embodiment of formula I, R7 is C2-C6-halogenalkenyl, in particular C2-C4-halogenalkenyl, more specifically C2-C3-halogenalkenyl such as CH═CHF, CH═CHCl, CH═CF2, CH═CCl2, CF═CF2, CCl═CCl2, CH2CH═CHF, CH2CH═CHCl, CH2CH═CF2, CH2CH═CCl2, CH2CF═CF2, CH2CCl═CCl2, CF2CF═CF2 or CCl2CCl═CCl2.


According to still a further embodiment of formula I, R7 is C2-C6-cycloalkenyl, in particular C2-C4-cycloalkenyl, such as CH═CH2-cPr.


According to still a further embodiment of formula I, R7 is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as C≡CH, C≡C—Cl, C≡C—CH3, CH2—C≡CH, CH2—C≡CCl or CH2—C≡C—CH3.


According to still a further embodiment of formula I, R7 is C2-C6-cycloalkynyl in particular C2-C4-cycloalkynyl, such as C≡C-cPr.


According to a further specific embodiment of formula I, R7 is C1-C6-alkoxy, in particular C1-C4-alkoxy, more specifically C1-C2-alkoxy such as OCH3, CH2CH3 or CH2OCH3.


According to a further specific embodiment of formula I, R7 is C1-C6-alkyl-C1-C6-alkoxy, in particular C1-C4-alkyl-C1-C4-alkoxy, more specifically C1-C2-alkyl-C1-C2-alkoxy, such as CH2OCH3 or CH2OCH2CH3.


According to a further specific embodiment of formula I, R7 is C2-C6-alkenyloxy, in particular C2-C4-alkenyloxy, more specifically C1-C2-alkenyloxy such as OCH═CH2, OCH2CH═CH2 OC(CH3)CH═CH2, CH2OCH═CH2, or CH2OCH2CH═CH2.


According to a further specific embodiment of formula I, R7 is C2-C6-alkynyloxy, in particular C2-C4-alkynyloxy, more specifically C1-C2-alkynyloxy such as OC≡CH, OCH2C≡CH or CH2OC≡CH


According to a further specific embodiment of formula I, R7 is C1-C6-halogenalkoxy, in particular C1-C4-halogenalkoxy, more specifically C1-C2-halogenalkoxy such as OCF3, OCHF2, OCH2F, OCCl3, OCHCl2 or OCH2Cl, in particular OCF3, OCHF2, OCCl3 or OCHCl2.


According to a further specific embodiment of formula I, R7 is C1-C6-alkyl-C1-C6-halogenalkoxy, in particular C1-C4-alkyl-C1-C4-halogenalkoxy, more specifically C1-C2-alkyl-C1-C2-halogenalkoxy such as CH2OCF3, CH2OCHF2, CH2OCH2F, CH2OCCl3, CH2OCHCl2 or CH2OCH2Cl, in particular CH2OCF3, CH2OCHF2, CH2OCCl3 or CH2OCHCl2.


According to a further specific embodiment of formula I, R7 is CH(═O), C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), C(═O)NH(C1-C6-alkyl) or C(═O)N(C1-C6-alkyl)2, wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.


According to a further specific embodiment of formula I, R7 is C1-C4-alkyl-CH(═O), C1-C4-alkyl-C(═O)C1-C6-alkyl, C1-C4-alkyl-C(═O)O(C1-C6-alkyl), C1-C4-alkyl-C(═O)NH(C1-C6-alkyl) or C1-C4-alkyl-C(═O)N(C1-C6-alkyl)2, especially CH2CH(═O), CH2C(═O)C1-C6-alkyl, CH2C(═O)O(C1-C6-alkyl), CH2C(═O)NH(C1-C6-alkyl) or CH2C(═O)N(C1-C6-alkyl)2 wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.


According to a further specific embodiment of formula I, R7 is CR′═NOR″ such as C(CH3)═NOCH3, C(CH3)═NOCH2CH3 or C(CH3)═NOCF3.


According to a further specific embodiment of formula I, R7 is C1-C6-alkyl-NH(C1-C4-alkyl) or C1-C6-alkyl-N(C1-C4-alkyl)2, wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.


According to a further specific embodiment of formula I, R7 is C1-C6-alkylthio, in particular C1-C4-alkoxy, more specifically C1-C3-alkylthio such as CH2SCH3 or CH2SCH2CH3.


According to a further specific embodiment of formula I, R7 is C1-C6-alkyl-S(O)n—C1-C6-alkyl, wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl and n is 1, 2 or 3.


According to a further specific embodiment of formula I, R7 is C1-C6-alkyl-S(O)n—C1-C6-halogenalkyl, wherein halogenalkyl is CF3 or CHF2 and n is 1, 2 or 3.


According to a further specific embodiment of formula I, R7 is C1-C6-alkyl-S(O)n-aryl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted with identical or different groups R7b which independently of one another are selected from halogen, C1-C2-alkyl, C1-C2-alkoxy, C1-C2-halogenalkyl, C1-C2-halogenalkoxy and S(O)n—C1-C6-alkyl, in particular F, Cl, Br, CH3, OCH3, CF3, CHF2, OCHF2, OCF3. According to one embodiment, R7 is unsubstituted phenyl. According to another embodiment, R7 is phenyl, that is substituted with one, two or three, in particular one, halogen, in particular selected from F, Cl and Br, more specifically selected from F and Cl.


According to a further specific embodiment of formula I, R7 is C1-C6-alkyl-NH—SO2—Rx wherein Rx is C1-C4-alkyl, C1-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted with one, two, three, four or five substituents Rx2 independently selected from C1-C4-alkyl, halogen, OH, CN, C1-C4-halogenalkyl, C1-C4-alkoxy, or C1-C4-halogenalkoxy, such as CH2NHSO2CF3 or CH2NHSO2CH3.


According to still another embodiment of formula I, R7 is selected from C1-C6-alkyl which is substituted, a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle, in particular three-, four-, five- or six-membered, wherein the carbocycle is unsubstituted or substituted with substituents R7b as defined below. According to one embodiment thereof, the carbocycle is unsubstituted.


According to one embodiment, R7 is selected from C1-C6-alkyl, especially CH2 which is substituted with a 3-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted with R7b.


According to one embodiment, R7 is selected from C1-C6-alkyl, especially CH2 which is substituted with a 4-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted with R7b.


According to one embodiment, R7 is selected from C1-C6-alkyl, especially CH2 which is substituted with a 5-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted with R7b.


According to one embodiment, R7 is selected from C1-C6-alkyl, especially CH2 which is substituted with a 6-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted with R7b.


According to a further specific embodiment of formula I, R7 is C1-C6-alkylheterocycle, especially CH2 substituted with a 4-membered saturated heterocycle which contains 1 or 2 heteroatoms, in particular 1 heteroatom, from the group consisting of N, O and S, as ring members. According to one embodiment, the heterocycle contains one O as heteroatom. For example, the formed heterocycle is oxetane. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted with R7b.


According to a further specific embodiment of formula I, R7 is C1-C6-alkylheterocycle, especially CH2 substituted with a 5-membered saturated heterocycle which contains 1, 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S, as ring members. According to one embodiment, the heterocycle contains one O as heteroatom. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted with R7b.


According to a further specific embodiment of formula I, R7 is C1-C6-alkylheterocycle, especially CH2 substituted by a 6-membered saturated heterocycle which contains 1, 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted with R7b. According to one specific embodiment thereof, said 6-membered saturated heterocycle contains 1 or 2, in particular 1, heteroatom(s) O. According to one embodiment thereof, the respective 6-membered heterocycle is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted with R7b.


According to a further specific embodiment of formula I, R7 is C1-C6-alkylheterocycle, especially CH2 substituted with a 5-membered saturated heterocycle which contains one N as ring member and optionally one or two groups CH2 are replaced by C(═O).


According to still another embodiment of formula I, R7 is a partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle, in particular three-, four-, five- or six-membered, wherein the carbocycle is unsubstituted or substituted with substituents R7b as defined below. According to one embodiment thereof, the carbocycle is unsubstituted.


According to still another embodiment of formula I, R7 is a partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the carbocycle and heterocycle are unsubstituted or substituted with substituents R7b as defined below. According to one embodiment thereof, the carbocycle or heterocycle is unsubstituted.


According to still a further embodiment, R7 is a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the carbocycle and heterocycle are unsubstituted or substituted with substituents R7b as defined below. According to one embodiment thereof, the carbocycle or heterocycle is unsubstituted.


According to still another embodiment of formula I, R7 is a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle, in particular three-, four-, five- or six-membered, wherein the carbocycle is unsubstituted or substituted with substituents R7b as defined below. According to one embodiment thereof, the carbocycle is unsubstituted.


According to one embodiment, R7 is a 3-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted with R7b.


According to one embodiment, R7 is a 3-membered saturated carbocycle, which is unsubstituted such as cyclopropyl.


According to one embodiment, R7 is a 3-membered saturated carbocycle, which is substituted with halogen, more specifically by F, such as C3H3F2.


According to one embodiment, R7 is a 3-membered saturated carbocycle, which is substituted with halogen. More specifically by Cl, such as C3H3Cl2.


According to one embodiment, R7 is a 4-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted with R7b.


According to one embodiment, R7 is a 5-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted with R7b.


According to one embodiment, R7 is a 6-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted with R7b.


According to still another embodiment of formula I, R7 is a partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the heterocycle is unsubstituted or substituted with substituents R7b as defined below. According to one embodiment thereof, the heterocycle is unsubstituted.


According to still another embodiment of formula I, R7 is a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the heterocycle is unsubstituted or substituted with substituents R7b as defined below. According to one embodiment thereof, the heterocycle is unsubstituted.


According to still another embodiment of formula I, in the embodiments of R7 described above, the heterocycle contains preferably one, two or three, more specifically one or two heteroatoms selected from N, O and S. More specifically, the heterocycle contains one heteroatom selected from N, O and S. In particular, the heterocycle contains one or two, in particular one O.


According to one embodiment, R7 is a 4-membered saturated heterocycle which contains 1 or 2 heteroatoms, in particular 1 heteroatom, from the group consisting of N, O and S, as ring members. According to one embodiment, the heterocycle contains one O as heteroatom. For example, the formed heterocycle is oxetane. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted with R7b.


According to still another embodiment of formula I, R7 is a 5-membered saturated heterocycle which contains 1, 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S, as ring members. According to one embodiment, the heterocycle contains one O as heteroatom. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted with R7b.


According to still another embodiment of formula I, R7 is a 6-membered saturated heterocycle which contains 1, 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted with R7b. According to one specific embodiment thereof, said 6-membered saturated heterocycle contains 1 or 2, in particular 1, heteroatom(s) O. According to one embodiment thereof, the respective 6-membered heterocycle is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted with R7b.


According to still another embodiment of formula I, R7 is phenyl-C1-C6-alkyl, such as phenyl-CH2, wherein the phenyl moiety in each case is unsubstituted or substituted with one, two or three identical or different groups R7b which independently of one another are selected from CN, halogen, C1-C2-alkyl, C1-C2-alkoxy, C1-C2-halogenalkyl, C1-C2-halogenalkoxy and S(O)n—C1-C6-alkyl, in particular from CN, F, Cl, Br, CH3, OCH3, CF3, CHF2, OCHF2, OCF3 and S(O)2CH3.


According to still another embodiment of formula I, R7 is aryl, in particular phenyl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted with identical or different groups R7b which independently of one another are selected from CN, halogen, C1-C2-alkyl, C1-C2-alkoxy, C1-C2-halogenalkyl, C1-C2-halogenalkoxy and S(O)n—C1-C6-alkyl, in particular from CN, F, Cl, Br, CH3, OCH3, CF3, CHF2, OCHF2, OCF3. According to one embodiment, R7 is unsubstituted phenyl. According to another embodiment, R7 is phenyl, that is substituted with one, two or three, in particular one, halogen, in particular selected from F, Cl and Br, more specifically selected from F and Cl.


According to still another embodiment of formula I, R7 is a 5-membered heteroaryl such as pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,2,4-triazolyl-1-yl, 1,2,4-triazol-3-yl 1,2,4-triazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl and 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl.


According to still another embodiment of formula I, R7 is a 6-membered heteroaryl, such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl and 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl.


According to a further specific embodiment of formula I, R7 is C1-C6-alkyl, especially CH2 substituted by a 5-membered saturated heteroaryl which contains 1, 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted by R7b.


According to a further specific embodiment of formula I, R7 is C1-C6-alkyl, especially CH2 substituted by a 5-membered saturated heteroaryl which contains one N as ring member. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted by R7b.


According to a further specific embodiment of formula I, R7 is C1-C6-alkyl, especially CH2 substituted by a 5-membered saturated heteroaryl which contains two N as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted by R7b.


According to a further specific embodiment of formula I, R7 is C1-C6-alkyl, especially CH2 substituted by a 5-membered saturated heteroaryl which contains three N as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted by R7b. According to one specific embodiment thereof, said 5-membered saturated heterocycle contains 1 or 2, in particular 1, heteroatom(s) O.


According to a further specific embodiment of formula I, R7 is C1-C6-alkyl, especially CH2 substituted by a 5-membered saturated heteroaryl which contains one S as ring member. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted by R7b.


According to a further specific embodiment of formula I, R7 is C1-C6-alkyl, especially CH2 substituted by a 5-membered saturated heteroaryl which contains one S and one N as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted by R7b.


According to a further specific embodiment of formula I, R7 is C1-C6-alkyl, especially CH2 substituted by a 5-membered saturated heteroaryl which contains one S and two N as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted by R7b.


According to a further specific embodiment of formula I, R7 is C1-C6-alkyl, especially CH2 substituted by a 5-membered saturated heteroaryl which contains one oxygen and one N as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted by R7b.


According to a further specific embodiment of formula I, R7 is C1-C6-alkyl, especially CH2 substituted by a 5-membered saturated heteroaryl which contains one oxygen and two N as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted by R7b.


According to a further specific embodiment of formula I, R7 is C1-C6-alkyl, especially CH2 substituted by a 6-membered saturated heteroaryl which contains 1, 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted by R7b.


According to a further specific embodiment of formula I, R7 is C1-C6-alkyl, especially CH2 substituted by a 6-membered saturated heteroaryl which one N as ring member. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted by R7b.


According to a further specific embodiment of formula I, R7 is C1-C6-alkyl, especially CH2 substituted by a 6-membered saturated heteroaryl which two N as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted by R7b.


According to a further specific embodiment of formula I, R7 is C1-C6-alkyl, especially CH2 substituted by a 10-membered saturated heteroaryl which contains 1, 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted by R7b. According to one specific embodiment thereof, said 10-membered saturated heterocycle contains 1 or 2, in particular 1, heteroatom(s) N.


According to a further specific embodiment of formula I, R7 is C1-C6-alkyl, especially CH2 substituted by a 10-membered saturated heteroaryl which one N as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted by R7b.


According to still another embodiment of formula I, R7 is CH2 substituted by a 5-membered heteroaryl such as pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,2,4-triazolyl-1-yl, 1,2,4-triazol-3-yl 1,2,4-triazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl and 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl.


According to still another embodiment of formula I, R7 is CH2 substituted by a 6-membered heteroaryl, such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl and 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl.


According to a further particular embodiment, R7 is selected from C1-C6-alkyl, C1-C6-halogenalkyl, CN, C2-C6-alkenyl, C2-C6-halogenalkenyl, C3-C6-cycloalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C1-C6-alkoxy, C3-C6-cycloalkynyl, C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), CR′═NOR″, C3-C6-halogencycloalkyl a saturated three-, four-, five-, six-, membered carbocycle or heterocycle, a five- or six-membered heteroaryl or aryl; and C1-C6-alkyl substituted by CN, C1-C6-alkoxy, C1-C4-halogenalkoxy, C1-C6-alkylthio, S(O)n—C1-C6-alkyl, NH—SO2—Rx, NH(C1-C6-alkyl), N(C1-C6-alkyl)2, C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), a saturated three-, four-, five-, six-, membered carbocycle, heterocycle, aryl or heteroaryl; wherein the carbocycle, heterocycle, aryl and heteroaryl is unsubstituted or carries one, two, three or four substituents R7b as defined below. According to one embodiment thereof, the carbocycle, heterocycle, heteroaryl and aryl are unsubstituted. In a particular embodiment, R7 is selected from CN, C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C1-C6-alkoxy, a saturated three-, four-, five-, six-, membered carbocycle or heterocycle, a five- or six-membered heteroaryl or aryl; and C1-C6-alkyl substituted by a saturated three-, four-, five-, six-, membered carbocycle, heterocycle, aryl or heteroaryl; wherein the carbocycle, heterocycle, aryl and heteroaryl are unsubstituted or carries one, two, three or four substituents R7b as defined below.


According to a further particular embodiment, R7 is selected from C1-C6-halogenalkyl, CN, C2-C6-alkenyl, C2-C6-halogenalkenyl, C3-C6-cycloalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C1-C6-alkoxy, C3-C6-cycloalkynyl, C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), CR′═NOR″, C3-C6-halogencycloalkyl a saturated three-, four-, five-, six-, membered carbocycle or heterocycle, a five- or six-membered heteroaryl or aryl; and C1-C6-alkyl substituted by CN, C1-C6-alkoxy, C1-C4-halogenalkoxy, C1-C6-alkylthio, S(O)n—C1-C6-alkyl, NH—SO2—Rx, NH(C1-C6-alkyl), N(C1-C6-alkyl)2, C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), a saturated three-, four-, five-, six-, membered carbocycle, heterocycle, aryl or heteroaryl; wherein the carbocycle, heterocycle, aryl and heteroaryl is unsubstituted or carries one, two, three or four substituents R7b as defined below. According to one embodiment thereof, the carbocycle, heterocycle, heteroaryl and aryl are unsubstituted. In a particular embodiment, R7 is selected from CN, C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C1-C6-alkoxy, a saturated three-, four-, five-, six-, membered carbocycle or heterocycle, a five- or six-membered heteroaryl or aryl; and C1-C6-alkyl substituted by a saturated three-, four-, five-, six-, membered carbocycle, heterocycle, aryl or heteroaryl; wherein the carbocycle, heterocycle, aryl and heteroaryl are unsubstituted or carries one, two, three or four substituents R7b as defined below.


Particularly preferred embodiments of R7 according to the invention are in Table P6 below, wherein each line of lines P6-1 to P6-208 corresponds to one particular embodiment of the invention, wherein P6-1 to P6-208 are also in any combination with one another a preferred embodiment of the present invention. The connection point to the carbon atom, to which R7 is bound is marked with “#” in the drawings.









TABLE P7:







(py = pyridyl):










No.
R7







P7-1
CH3



P7-2
CH2CH3



P7-3
CF3



P7-4
CH2F



P7-5
CH2Cl



P7-6
CHF2



P7-7
CHCl2



P7-8
CH2CF3



P7-9
CH2CCl3



P7-10
CF2CHF2



P7-11
CH2OCH3



P7-12
CH2OCH2F



P7-13
CH2OCHF2



P7-14
CH2OCF3



P7-15
CH2OCF2CHF2



P7-16
CH2NHMe



P7-17
CH2SMe



P7-18
CH2SOMe



P7-19
CH2SO2Me



P7-20
CH2NMe2



P7-21
CH2NSO2CF3



P7-22
CH2NSO2CH3



P7-23
CN



P7-24
CH2CN



P7-25
CHO



P7-26
COMe



P7-27
CO2Me



P7-28
CH2CHO



P7-29
CH2COMe



P7-30
CH2CO2Me







P7-31


embedded image









P7-32


embedded image









P7-33


embedded image









P7-34


embedded image









P7-35


embedded image









P7-36


embedded image









P7-37


embedded image









P7-38


embedded image









P7-39


embedded image









P7-40


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P7-41


embedded image









P7-42


embedded image









P7-43


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P7-44


embedded image









P7-45


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P7-46


embedded image









P7-47


embedded image









P7-48


embedded image









P7-49


embedded image









P7-50


embedded image









P7-51


embedded image









P7-52


embedded image









P7-53


embedded image









P7-54


embedded image









P7-55


embedded image









P7-56


embedded image









P7-57


embedded image









P7-58


embedded image









P7-59


embedded image









P7-60


embedded image









P7-61


embedded image









P7-62


embedded image









P7-63
C6H5



P7-64
4-Cl—C6H4



P7-65
3-Cl—C6H4



P7-66
2-Cl—C6H4



P7-67
2,4-Cl2—C6H3



P7-68
4-F—C6H4



P7-69
3-F—C6H4



P7-70
2-F—C6H4



P7-71
2,4-F2—C6H3



P7-72
4-MeO—C6H4



P7-73
3-MeO—C6H4



P7-74
2-MeO—C6H4



P7-75
4-MeO2S—C6H4



P7-76
3-MeO2S—C6H4



P7-77
2-MeO2S—C6H4



P7-78
—CH2—C6H5



P7-79
—CH2—C6H4—4-F



P7-80
—CH2—C6H4—4-Cl



P7-81
—CH2—C6H3—2,4-Cl2



P7-82
—CH2—C6H4—4-SO2Me



P7-83
3-py



P7-84
2-py



P7-85
4-py







P7-86


embedded image









P7-87


embedded image









P7-88


embedded image









P7-89


embedded image









P7-90


embedded image









P7-91


embedded image









P7-92


embedded image









P7-93


embedded image









P7-94


embedded image









P7-95


embedded image









P7-96


embedded image









P7-97


embedded image









P7-98


embedded image









P7-99


embedded image









P7-100


embedded image









P7-101


embedded image









P7-102


embedded image









P7-103


embedded image









P7-104


embedded image









P7-105


embedded image









P7-106


embedded image









P7-107


embedded image









P7-108


embedded image









P7-109


embedded image









P7-110


embedded image









P7-111


embedded image









P7-112


embedded image









P7-113


embedded image









P7-114


embedded image









P7-115


embedded image









P7-116


embedded image









P7-117


embedded image









P7-118


embedded image









P7-119


embedded image









P7-120


embedded image









P7-121


embedded image









P7-122


embedded image









P7-123


embedded image









P7-124


embedded image









P7-125


embedded image









P7-126


embedded image









P7-127


embedded image









P7-128


embedded image









P7-129


embedded image









P7-130


embedded image









P7-131


embedded image









P7-132


embedded image









P7-133


embedded image









P7-134


embedded image









P7-135


embedded image









P7-136


embedded image









P7-137


embedded image









P7-138


embedded image









P7-139


embedded image









P7-140


embedded image









P7-141


embedded image









P7-142


embedded image









P7-143


embedded image









P7-144


embedded image









P7-145


embedded image









P7-146


embedded image









P7-147


embedded image









P7-148


embedded image









P7-149


embedded image









P7-150


embedded image









P7-151


embedded image









P7-152


embedded image









P7-153


embedded image









P7-154


embedded image









P7-155


embedded image









P7-156


embedded image









P7-157


embedded image









P7-158


embedded image









P7-159


embedded image









P7-160


embedded image









P7-161


embedded image









P7-162


embedded image









P7-163


embedded image









P7-164


embedded image









P7-165


embedded image









P7-166


embedded image









P7-167


embedded image









P7-168


embedded image









P7-169


embedded image









P7-170


embedded image









P7-171


embedded image









P7-172


embedded image









P7-173


embedded image









P7-174


embedded image









P7-175


embedded image









P7-176


embedded image









P7-177


embedded image









P7-178


embedded image









P7-179


embedded image









P7-180


embedded image









P7-181


embedded image









P7-182


embedded image









P7-183
CH2CH2CH3



P7-184
CH(CH3)2



P7-185
CH2CH2CH2CH3



P7-186
CH(CH3)CH2CH3



P7-187
CH2CH(CH3)CH3



P7-188
C(CH3)3



P7-189
—O—C6H5



P7-190
—O—C6H4—2-F



P7-191
—O—C6H4—3-F



P7-192
—O—C6H4—4-F



P7-193
—O—C6H4—2-Cl



P7-194
—O—C6H4—3-Cl



P7-195
—O—C6H4—4-Cl



P7-196
—O—C6H4—2-OCH3



P7-197
—O—C6H4—3-OCH3



P7-198
—O—C6H4—4-OCH3



P7-199
—NH—C6H5



P7-200
—NH—C6H4—2-F



P7-201
—NH—C6H4—3-F



P7-202
—NH—C6H4—4-F



P7-203
—NH—C6H4—2-Cl



P7-204
—NH—C6H4—3-Cl



P7-205
—NH—C6H4—4-Cl



P7-206
—NH—C6H4—2-OCH3



P7-207
—NH—C6H4—3-OCH3



P7-208
—NH—C6H4—4-OCH3










R8 is independently selected from CN, C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, CH(═O), C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), C(═O)NH(C1-C6-alkyl), C(═O)N(C1-C6-alkyl)2, CR′═NOR″, a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, a five- or six-membered heteroaryl or aryl; wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(═O) and C(═S), and wherein the heterocycle and heteroaryl contain independently one, two, three or four heteroatoms selected from N, O and S, and wherein heterocycle and heteroaryl are connected via C atom; and wherein R′ and R″ are independently selected from H, C1-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl or aryl;


wherein the heterocycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S, and wherein R′ and R″ are independently unsubstituted or substituted with R′″ which is independently selected from halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C1-C6-alkoxy, C1-C6-halogenalkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and phenyl;


wherein Rx is as defined above;


wherein the acyclic moieties of R8 are independently not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R8a, which independently of one another are selected from:


R8a halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkoxy, C1-C4-halogenalkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C6-alkylthio, C1-C6-halogenalkylthio, S(O)n—C1-C6-alkyl, S(O)n-aryl, CH(═O), C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), C(═O)NH(C1-C6-alkyl), C(═O)N(C1-C6-alkyl)2, CR′═NOR″, a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- or heterocycle, a five-, six- or ten-membered heteroaryl, aryl or phenoxy, wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(═O) and C(═S), and wherein the heterocycle and heteroaryl contains independently one, two, three or four heteroatoms selected from N, O and S, and wherein heterocycle and heteroaryl are connected via C atom; wherein the carbo-, heterocyclic, heteroaryl and phenyl groups are independently unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkylthio, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, and S(O)n—C1-C6-alkyl; and wherein Rx, R′ and R″ are as defined above; n is 0, 1, 2; and


wherein the carbo-, heterocyclic, heteroaryl and aryl moieties of R8 are independently unsubstituted or substituted with identical or different groups R8b, which independently of one another are selected from:


R8b halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy, C1-C6-alkylthio, C1-C6-halogenalkylthio, S(O)n—C1-C6-alkyl, C1-C4-alkoxy-C1-C4-alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy; and wherein Rx and n are as defined above.


According to one embodiment of formula I, R8 is selected from substituted C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C3-C6-cycloalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkynyl, CN, CH(═O), C(═O)C2-C6-alkyl, C(═O)O(C2-C6-alkyl), CR′═NOR″, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C6-alkyl-five- and six-membered heteroaryl, a five- or six-membered heteroaryl, benzyl, aryl; wherein R′ and R″ are defined below; and wherein the acyclic moieties of R8 are unsubstituted or substituted with identical or different groups R8a as defined below and wherein wherein the carbocycle, heterocycle and heteroaryl and aryl moieties are unsubstituted or substituted with substituents R8b as defined below.


According to still another embodiment of formula I, R8 is CN.


According to still another embodiment of formula I, R8 is selected from CN, substituted C1-C6-alkyl, C1-C6-halogenalkyl or C1-C6-alkyl which is substituted, C1-C6-halogenalkyl, phenyl, halogenphenyl and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or is substituted with substituents R8b as defined below.


According to one embodiment thereof, the carbocycle is unsubstituted. In a particular embodiment, R8 is selected from C1-C6-halogenalkyl, phenyl-CH2, halogenphenyl-CH2, phenyl, halogenphenyl and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or is substituted with substituents R8b as defined below.


According to still another embodiment of formula I, R8 is selected from CN, substituted C1-C6-alkyl, C1-C6-halogenalkyl or C1-C6-alkyl which is substituted, C1-C6-halogenalkyl, phenyl, halogenphenyl and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or substituted by substituents R8b as defined below. According to one embodiment thereof, the carbo- and heterocycle is unsubstituted. In a particular embodiment, R8 is selected from substituted C1-C6-halogenalkyl, phenyl, halogenphenyl and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or substituted by substituents R8b as defined below.


According to another embodiment of formula I, R8 is selected from CN, substituted C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C6-alkylaryl, five- or six-membered heteroaryl or aryl which is unsubstituted or substituted with halogen or C1-C6-halogenalkyl, and wherein the acyclic moieties of R8 are unsubstituted or substituted with identical or different groups R8a as defined below and wherein wherein the carbocycle, heterocycle and heteroaryl and aryl moieties are unsubstituted or substituted with substituents R8b as defined below.


According to still another embodiment of formula I, R8 is selected from CN, substituted C1-C6-alkyl, C1-C6-halogenalkyl, CN, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C6-alkylaryl, phenyl, pyridine, pyrimidine, thiophene, imidazole, triazol, oxadiazol wherein the acyclic moieties of R8 are unsubstituted or substituted with identical or different groups R8a as defined below and wherein wherein the carbocycle, heterocycle and heteroaryl and aryl moieties are unsubstituted or substituted with substituents R8b as defined below.


According to still another embodiment of formula I, R8 is C1-C6-alkyl such as CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.


According to still another embodiment of formula I, R8 is C1-C6-alkyl such as CH3.


According to still another embodiment of formula I, R8 is C1-C6-alkyl such as C2H5.


According to still another embodiment of formula I, R8 is C1-C6-alkyl such as CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl which is substituted with at least one group R8a, which independently of one another are selected from:


R8a halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkoxy, C1-C4-halogenalkoxy, C1-C6-alkylthio, C1-C6-halogenalkylthio, S(O)n—C1-C6-alkyl, S(O)n-aryl, CH(═O), C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), C(═O)NH(C1-C6-alkyl), C(═O)N(C1-C6-alkyl)2, CR′═NOR″ a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, five-, six- or ten-membered heteroaryl, aryl or phenoxy, wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(═O) and C(═S), and wherein the heterocycle and heteroaryl contains independently one, two, three or four heteroatoms selected from N, O and S; wherein the carbocyclic, heterocyclic, heteroaryl, aryl groups are independently unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkylthio, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, and S(O)n—C1-C6-alkyl.


According to still another embodiment of formula I, R8 is CH3 is substituted with at least one group R8a, which independently of one another are selected from:


R8a halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkoxy, C1-C4-halogenalkoxy, C1-C6-alkylthio, C1-C6-halogenalkylthio, S(O)n—C1-C6-alkyl, S(O)n-aryl, CH(═O), C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), C(═O)NH(C1-C6-alkyl), C(═O)N(C1-C6-alkyl)2, CR′═NOR″, a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, five-, six- or ten-membered heteroaryl, an aryl or phenoxy, wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(═O) and C(═S), and wherein the heterocycle and heteroaryl contains independently one, two, three or four heteroatoms selected from N, O and S; wherein the carbocyclic, heterocyclic, heteroaryl, heteroaryl and phenyl groups are independently unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkylthio, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, and S(O)n—C1-C6-alkyl.


According to still another embodiment of formula I, R8 is C2H5 is substituted with at least one group R8a, which independently of one another are selected from:


R8a halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkoxy, C1-C4-halogenalkoxy, C1-C6-alkylthio, C1-C6-halogenalkylthio, S(O)n—C1-C6-alkyl, S(O)n-aryl, CH(═O), C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), C(═O)NH(C1-C6-alkyl), C(═O)N(C1-C6-alkyl)2, CR′═NOR″ a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, five-, six- or ten-membered heteroaryl, phenyl or phenoxy; wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(═O) and C(═S), and wherein the heterocycle and heteroaryl contains independently one, two, three or four heteroatoms selected from N, O and S; wherein the carbocyclic, heterocyclic, heteroaryl, aryl and phenyl groups are independently unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, CN, NO2, SH, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, NH(C(═O)C1-C4-alkyl), N(C(═O)C1-C4-alkyl)2, NH—SO2—Rx, C1-C6-alkylthio, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, and S(O)n—C1-C6-alkyl.


According to still another embodiment of formula I, R8 is CH2CN.


According to still another embodiment of formula I, R8 is CH2OH.


According to still another embodiment of formula I, R8 is C1-C6-halogenalkyl, in particular C1-C4-halogenalkyl, more specifically C1-C2-halogenalkyl, such as CF3, CCl3, FCH2, ClCH2, F2CH, Cl2CH, CF3CH2, CCl3CH2 or CF2CHF2.


According to still another embodiment of formula I, R8 is CH2F.


According to still another embodiment of formula I, R8 is CHF2.


According to still another embodiment of formula I, R8 is CF3.


According to still a further embodiment of formula I, R8 is C2-C6-alkenyl, in particular C2-C4-alkenyl, such as CH═CH2, CH2CH═CH2 or C(CH3)C═CH2.


According to a further specific embodiment of formula I, R8 is C2-C6-halogenalkenyl, in particular C2-C4-halogenalkenyl, more specifically C2-C3-halogenalkenyl such as CH═CHF, CH═CHCl, CH═CF2, CH═CCl2, CF═CF2, CCl═CCl2, CH2CH═CHF, CH2CH═CHCl, CH2CH═CF2, CH2CH═CCl2, CH2CF═CF2, CH2CCl═CCl2, CF2CF═CF2 or CCl2CCl═CCl2.


According to still a further embodiment of formula I, R8 is C2-C6-cycloalkenyl, in particular C2-C4-cycloalkenyl, such as CH═CH2-cPr.


According to still a further embodiment of formula I, R8 is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as C≡CH, C≡C—Cl, C≡C—CH3, CH2—C≡CH, CH2—C≡CCl or CH2—C≡C—CH3.


According to still a further embodiment of formula I, R8 is C2-C6-cycloalkynyl in particular C2-C4-cycloalkynyl, such as C≡C-cPr.


According to a further specific embodiment of formula I, R8 is CH(═O), C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), C(═O)NH(C1-C6-alkyl) or C(═O)N(C1-C6-alkyl)2, wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.


According to a further specific embodiment of formula I, R8 is C1-C4-alkyl-CH(═O), C1-C4-alkyl-C(═O)C1-C6-alkyl, C1-C4-alkyl-C(═O)O(C1-C6-alkyl), C1-C4-alkyl-C(═O)NH(C1-C6-alkyl) or C1-C4-alkyl-C(═O)N(C1-C6-alkyl)2, especially CH2CH(═O), CH2C(═O)C1-C6-alkyl, CH2C(═O)O(C1-C6-alkyl), CH2C(═O)NH(C1-C6-alkyl) or CH2C(═O)N(C1-C6-alkyl)2 wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.


According to a further specific embodiment of formula I, R8 is CR′═NOR″ such as C(CH3)═NOCH3, C(CH3)═NOCH2CH3 or C(CH3)═NOCF3.


According to a further specific embodiment of formula I, R8 is C1-C6-alkyl-NH(C1-C4-alkyl) or C1-C6-alkyl-N(C1-C4-alkyl)2, wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.


According to a further specific embodiment of formula I, R8 is C1-C6-alkylthio, in particular C1-C4-alkoxy, more specifically C1-C3-alkylthio such as CH2SCH3 or CH2SCH2CH3.


According to a further specific embodiment of formula I, R8 is C1-C6-alkyl-S(O)n—C1-C6-alkyl, wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl and n is 1, 2 or 3.


According to a further specific embodiment of formula I, R8 is C1-C6-alkyl-S(O)n—C1-C6-halogenalkyl, wherein halogenalkyl is CF3 or CHF2 and n is 1, 2 or 3.


According to a further specific embodiment of formula I, R8 is C1-C6-alkyl-S(O)n-aryl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted with identical or different groups R8b which independently of one another are selected from halogen, C1-C2-alkyl, C1-C2-alkoxy, C1-C2-halogenalkyl, C1-C2-halogenalkoxy and S(O)n—C1-C6-alkyl, in particular F, Cl, Br, CH3, OCH3, CF3, CHF2, OCHF2, OCF3. According to one embodiment, R8 is unsubstituted phenyl. According to another embodiment, R8 is phenyl, that is substituted with one, two or three, in particular one, halogen, in particular selected from F, Cl and Br, more specifically selected from F and Cl.


According to a further specific embodiment of formula I, R8 is C1-C6-alkyl-NH—SO2—Rx wherein Rx is C1-C4-alkyl, C1-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted with one, two, three, four or five substituents Rx2 independently selected from C1-C4-alkyl, halogen, OH, CN, C1-C4-halogenalkyl, C1-C4-alkoxy, or C1-C4-halogenalkoxy, such as CH2NHSO2CF3 or CH2NHSO2CH3.


According to still another embodiment of formula I, R8 is selected from C1-C6-alkyl which is substituted, a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle, in particular three-, four-, five- or six-membered, wherein the carbocycle is unsubstituted or substituted with substituents R8b as defined below. According to one embodiment thereof, the carbocycle is unsubstituted.


According to one embodiment, R8 is selected from C1-C6-alkyl, especially CH2 which is substituted with a 3-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b.


According to one embodiment, R8 is selected from C1-C6-alkyl, especially CH2 which is substituted with a 4-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent Rb. According to still another embodiment of formula I, it is substituted with R8b.


According to one embodiment, R8 is selected from C1-C6-alkyl, especially CH2 which is substituted with a 5-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b.


According to one embodiment, R8 is selected from C1-C6-alkyl, especially CH2 which is substituted with a 6-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent Rb. According to still another embodiment of formula I, it is substituted with R8b.


According to a further specific embodiment of formula I, R8 is C1-C6-alkylheterocycle, especially CH2 substituted with a 4-membered saturated heterocycle which contains 1 or 2 heteroatoms, in particular 1 heteroatom, from the group consisting of N, O and S, as ring members. According to one embodiment, the heterocycle contains one O as heteroatom. For example, the formed heterocycle is oxetane. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b.


According to a further specific embodiment of formula I, R8 is C1-C6-alkylheterocycle, especially CH2 substituted with a 5-membered saturated heterocycle which contains 1, 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S, as ring members. According to one embodiment, the heterocycle contains one O as heteroatom. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b.


According to a further specific embodiment of formula I, R8 is C1-C6-alkylheterocycle, especially CH2 substituted by a 6-membered saturated heterocycle which contains 1, 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent Rb.


According to still another embodiment of formula I, it is substituted with R8b. According to one specific embodiment thereof, said 6-membered saturated heterocycle contains 1 or 2, in particular 1, heteroatom(s) O. According to one embodiment thereof, the respective 6-membered heterocycle is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b.


According to a further specific embodiment of formula I, R8 is C1-C6-alkylheterocycle, especially CH2 substituted with a 5-membered saturated heterocycle which contains one N as ring member and optionally one or two groups CH2 are replaced by C(═O).


According to still another embodiment of formula I, R8 is a partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle, in particular three-, four-, five- or six-membered, wherein the carbocycle is unsubstituted or substituted with substituents R8b as defined below. According to one embodiment thereof, the carbocycle is unsubstituted.


According to still another embodiment of formula I, R8 is a partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the carbocycle and heterocycle are unsubstituted or substituted with substituents R8b as defined below. According to one embodiment thereof, the carbocycle or heterocycle is unsubstituted.


According to still a further embodiment, R8 is a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the carbocycle and heterocycle are unsubstituted or substituted with substituents R8b as defined below. According to one embodiment thereof, the carbocycle or heterocycle is unsubstituted.


According to still another embodiment of formula I, R8 is a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle, in particular three-, four-, five- or six-membered, wherein the carbocycle is unsubstituted or substituted with substituents R8b as defined below. According to one embodiment thereof, the carbocycle is unsubstituted.


According to one embodiment, R8 is a 3-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b.


According to one embodiment, R8 is a 3-membered saturated carbocycle, which is unsubstituted such as cyclopropyl.


According to one embodiment, R8 is a 3-membered saturated carbocycle, which is substituted with halogen, more specifically by F, such as C3H3F2.


According to one embodiment, R8 is a 3-membered saturated carbocycle, which is substituted with halogen. More specifically by Cl, such as C3H3Cl2.


According to one embodiment, R8 is a 4-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R8b.


According to still another embodiment of formula I, it is substituted with R8b.


According to one embodiment, R8 is a 5-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent Rb. According to still another embodiment of formula I, it is substituted with R8b.


According to one embodiment, R8 is a 6-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b.


According to still another embodiment of formula I, R8 is a partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the heterocycle is unsubstituted or substituted with substituents R8b as defined below. According to one embodiment thereof, the heterocycle is unsubstituted.


According to still another embodiment of formula I, R8 is a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the heterocycle is unsubstituted or substituted with substituents R8b as defined below. According to one embodiment thereof, the heterocycle is unsubstituted.


According to still another embodiment of formula I, in the embodiments of R8 described above, the heterocycle contains preferably one, two or three, more specifically one or two heteroatoms selected from N, O and S. More specifically, the heterocycle contains one heteroatom selected from N, O and S. In particular, the heterocycle contains one or two, in particular one O.


According to one embodiment, R8 is a 4-membered saturated heterocycle which contains 1 or 2 heteroatoms, in particular 1 heteroatom, from the group consisting of N, O and S, as ring members. According to one embodiment, the heterocycle contains one O as heteroatom. For example, the formed heterocycle is oxetane. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent Rb. According to still another embodiment of formula I, it is substituted with R8b.


According to still another embodiment of formula I, R8 is a 5-membered saturated heterocycle which contains 1, 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S, as ring members. According to one embodiment, the heterocycle contains one O as heteroatom. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b.


According to still another embodiment of formula I, R8 is a 6-membered saturated heterocycle which contains 1, 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b. According to one specific embodiment thereof, said 6-membered saturated heterocycle contains 1 or 2, in particular 1, heteroatom(s) O. According to one embodiment thereof, the respective 6-membered heterocycle is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b.


According to still another embodiment of formula I, R8 is phenyl-C1-C6-alkyl, such as phenyl-CH2, wherein the phenyl moiety in each case is unsubstituted or substituted with one, two or three identical or different groups R8b which independently of one another are selected from CN, halogen, C1-C2-alkyl, C1-C2-alkoxy, C1-C2-halogenalkyl, C1-C2-halogenalkoxy and S(O)n—C1-C6-alkyl, in particular from CN, F, Cl, Br, CH3, OCH3, CF3, CHF2, OCHF2, OCF3 and S(O)2CH3.


According to still another embodiment of formula I, R8 is aryl, in particular phenyl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted with identical or different groups R8b which independently of one another are selected from CN, halogen, C1-C2-alkyl, C1-C2-alkoxy, C1-C2-halogenalkyl, C1-C2-halogenalkoxy and S(O)n—C1-C6-alkyl, in particular from CN, F, Cl, Br, CH3, OCH3, CF3, CHF2, OCHF2, OCF3. According to one embodiment, R8 is unsubstituted phenyl. According to another embodiment, R8 is phenyl, that is substituted with one, two or three, in particular one, halogen, in particular selected from F, Cl and Br, more specifically selected from F and Cl.


According to still another embodiment of formula I, R8 is a 5-membered heteroaryl such as pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,2,4-triazolyl-1-yl, 1,2,4-triazol-3-yl 1,2,4-triazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl and 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl.


According to still another embodiment of formula I, R8 is a 6-membered heteroaryl, such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl and 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl.


According to a further specific embodiment of formula I, R8 is C1-C6-alkyl, especially CH2 substituted by a 5-membered saturated heteroaryl which contains 1, 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent Rb. According to still another embodiment of formula I, it is substituted by R8b.


According to a further specific embodiment of formula I, R8 is C1-C6-alkyl, especially CH2 substituted by a 5-membered saturated heteroaryl which contains one N as ring member. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted by R8b.


According to a further specific embodiment of formula I, R8 is C1-C6-alkyl, especially CH2 substituted by a 5-membered saturated heteroaryl which contains two N as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted by R8b.


According to a further specific embodiment of formula I, R8 is C1-C6-alkyl, especially CH2 substituted by a 5-membered saturated heteroaryl which contains three N as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted by R8b. According to one specific embodiment thereof, said 5-membered saturated heterocycle contains 1 or 2, in particular 1, heteroatom(s) O.


According to a further specific embodiment of formula I, R8 is C1-C6-alkyl, especially CH2 substituted by a 5-membered saturated heteroaryl which contains one S as ring member. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted by R8b.


According to a further specific embodiment of formula I, R8 is C1-C6-alkyl, especially CH2 substituted by a 5-membered saturated heteroaryl which contains one S and one N as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted by R8b.


According to a further specific embodiment of formula I, R8 is C1-C6-alkyl, especially CH2 substituted by a 5-membered saturated heteroaryl which contains one S and two N as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted by R8b.


According to a further specific embodiment of formula I, R8 is C1-C6-alkyl, especially CH2 substituted by a 5-membered saturated heteroaryl which contains one oxygen and one N as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted by R8b.


According to a further specific embodiment of formula I, R8 is C1-C6-alkyl, especially CH2 substituted by a 5-membered saturated heteroaryl which contains one oxygen and two N as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted by R8b.


According to a further specific embodiment of formula I, R8 is C1-C6-alkyl, especially CH2 substituted by a 6-membered saturated heteroaryl which contains 1, 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent Rb. According to still another embodiment of formula I, it is substituted by R8b.


According to a further specific embodiment of formula I, R8 is C1-C6-alkyl, especially CH2 substituted by a 6-membered saturated heteroaryl which one N as ring member. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted by R8b.


According to a further specific embodiment of formula I, R8 is C1-C6-alkyl, especially CH2 substituted by a 6-membered saturated heteroaryl which two N as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent Rb. According to still another embodiment of formula I, it is substituted by R8b.


According to a further specific embodiment of formula I, R8 is C1-C6-alkyl, especially CH2 substituted by a 10-membered saturated heteroaryl which contains 1, 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted by R8b. According to one specific embodiment thereof, said 10-membered saturated heterocycle contains 1 or 2, in particular 1, heteroatom(s) N.


According to a further specific embodiment of formula I, R8 is C1-C6-alkyl, especially CH2 substituted by a 10-membered saturated heteroaryl which one N as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted by R8b.


According to still another embodiment of formula I, R8 is CH2 substituted by a 5-membered heteroaryl such as pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,2,4-triazolyl-1-yl, 1,2,4-triazol-3-yl 1,2,4-triazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl and 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl.


According to still another embodiment of formula I, R8 is CH2 substituted by a 6-membered heteroaryl, such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl and 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl.


According to a further particular embodiment, R8 is selected from C1-C6-alkyl, C1-C6-halogenalkyl, CN, C2-C6-alkenyl, C2-C6-halogenalkenyl, C3-C6-cycloalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C1-C6-alkoxy, C3-C6-cycloalkynyl, C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), CR′═NOR″, C3-C6-halogencycloalkyl a saturated three-, four-, five-, six-, membered carbocycle or heterocycle, a five- or six-membered heteroaryl or aryl; and C1-C6-alkyl substituted by CN, C1-C6-alkoxy, C1-C4-halogenalkoxy, C1-C6-alkylthio, S(O)n—C1-C6-alkyl, NH—SO2—Rx, NH(C1-C6-alkyl), N(C1-C6-alkyl)2, C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), a saturated three-, four-, five-, six-, membered carbocycle, heterocycle, aryl or heteroaryl; wherein the carbocycle, heterocycle, aryl and heteroaryl is unsubstituted or carries one, two, three or four substituents R8b as defined below. According to one embodiment thereof, the carbocycle, heterocycle, heteroaryl and aryl are unsubstituted. In a particular embodiment, R8 is selected from CN, C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C1-C6-alkoxy, a saturated three-, four-, five-, six-, membered carbocycle or heterocycle, a five- or six-membered heteroaryl or aryl; and C1-C6-alkyl substituted by a saturated three-, four-, five-, six-, membered carbocycle, heterocycle, aryl or heteroaryl; wherein the carbocycle, heterocycle, aryl and heteroaryl are unsubstituted or carries one, two, three or four substituents R8b as defined below.


According to a further particular embodiment, R8 is selected from C1-C6-halogenalkyl, CN, C2-C6-alkenyl, C2-C6-halogenalkenyl, C3-C6-cycloalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C1-C6-alkoxy, C3-C6-cycloalkynyl, C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), CR′═NOR″, C3-C6-halogencycloalkyl a saturated three-, four-, five-, six-, membered carbocycle or heterocycle, a five- or six-membered heteroaryl or aryl; and C1-C6-alkyl substituted by CN, C1-C6-alkoxy, C1-C4-halogenalkoxy, C1-C6-alkylthio, S(O)n—C1-C6-alkyl, NH—SO2—Rx, NH(C1-C6-alkyl), N(C1-C6-alkyl)2, C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), a saturated three-, four-, five-, six-, membered carbocycle, heterocycle, aryl or heteroaryl; wherein the carbocycle, heterocycle, aryl and heteroaryl is unsubstituted or carries one, two, three or four substituents R8b as defined below. According to one embodiment thereof, the carbocycle, heterocycle, heteroaryl and aryl are unsubstituted. In a particular embodiment, R8 is selected from CN, C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C1-C6-alkoxy, a saturated three-, four-, five-, six-, membered carbocycle or heterocycle, a five- or six-membered heteroaryl or aryl; and C1-C6-alkyl substituted by a saturated three-, four-, five-, six-, membered carbocycle, heterocycle, aryl or heteroaryl; wherein the carbocycle, heterocycle, aryl and heteroaryl are unsubstituted or carries one, two, three or four substituents R8b as defined below.


Particularly preferred embodiments of R8 according to the invention are in Table P8 below, wherein each line of lines P8-1 to P8-188 corresponds to one particular embodiment of the invention, wherein P8-1 to P8-188 are also in any combination with one another a preferred embodiment of the present invention. The connection point to the carbon atom, to which R8 is bound is marked with “#” in the drawings.









TABLE P8







(py = pyridyl):










No.
R8







P
CH3



P
CH2CH3



P
CF3



P8-4
CH2F



P8-5
CH2Cl



P8-6
CHF2



P8-7
CHCl2



P8-8
CH2CF3



P8-9
CH2CCl3



P8-10
CF2CHF2



P8-11
CH2OCH3



P8-12
CH2OCH2F



P8-13
CH2OCHF2



P8-14
CH2OCF2



P8-15
CH2OCF2CHF2



P8-16
CH2NHMe



P8-17
CH2SMe



P8-18
CH2SOMe



P8-19
CH2SO2Me



P8-20
CH2NMe2



P8-21
CH2NSO2CF3



P8-22
CH2NSO2CH3



P8-23
CN



P8-24
CH2CN



P8-25
CHO



P8-26
COMe



P8-27
CO2Me



P8-28
CH2CHO



P8-29
CH2COMe



P8-30
CH2CO2Me







P8-31


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P8-32


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P8-33


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P8-34


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P8-35


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P8-36


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P8-37


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P8-38


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P8-39


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P8-40


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P8-41


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P8-42


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P8-43


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P8-44


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P8-45


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P8-46


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P8-47


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P8-48


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P8-49


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P8-50


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P8-51


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P8-52


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P8-53


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P8-54


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P8-55


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P8-56


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P8-57


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P8-58


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P8-59


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P8-60


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P8-61


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P8-62


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P8-63
C6H5



P8-64
4-Cl—C6H4



P8-65
3-Cl—C6H4



P8-66
2-Cl—C6H4



P8-67
2,4-Cl2 C6H3



P8-68
4-F—C6H4



P8-69
3-F—C6H4



P8-70
2-F—C6H4



P8-71
2,4-F2—C6H3



P8-72
4-MeO—C6H4



P8-73
3-MeO—C6H4



P8-74
2-MeO—C6H4



P8-75
4-MeO2S—C6H4



P8-76
3-MeO2S—C6H4



P8-77
2-MeO2S—C6H4



P8-78
—CH2—C6H5



P8-79
—CH2—C6H4—4-F



P8-80
—CH2—C6H4—4-Cl



P8-81
—CH2—C6H3—2,4-Cl2



P8-82
—CH2—C6H4—4-SO2Me



P8-83
3-py



P8-84
2-py



P8-85
4-py







P8-86


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P8-87


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P8-88


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P8-89


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P8-90


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P8-91


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P8-92


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P8-93


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P8-94


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P8-95


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P8-96


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P8-97


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P8-98


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P8-99


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P8-100


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P8-101


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P8-102


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P8-103


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P8-104


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P8-105


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P8-106


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P8-107


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P8-108


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P8-109


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P8-110


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P8-111


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P8-112


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P8-113


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P8-114


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P8-115


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P8-116


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P8-117


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P8-118


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P8-119


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P8-120


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P8-121


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P8-122


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P8-123


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P8-124


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P8-125


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P8-126


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P8-127


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P8-128


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P8-129


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P8-130


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P8-131


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P8-132


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P8-133


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P8-134


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P8-135


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P8-136


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P8-137


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P8-138


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P8-139


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P8-140


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P8-141


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P8-142


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P8-143


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P8-144


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P8-145


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P8-146


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P8-147


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P8-148


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P8-149


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P8-150


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P8-151


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P8-152


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P8-153


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P8-154


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P8-155


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P8-156


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P8-157


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P8-158


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P8-159


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P8-160


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P8-161


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P8-162


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P8-163


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P8-164


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P8-165


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P8-166


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P8-167


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P8-168


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P8-169


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P8-170


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P8-171


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P8-172


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P8-173


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P8-174


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P8-175


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P8-176


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P8-177


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P8-178


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P8-179


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P8-180


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P8-181


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P8-182


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P8-183
CH2CH2CH3



P8-184
CH(CH3)2



P8-185
CH2CH2CH2CH3



P8-186
CH(CH3)CH2CH3



P8-187
CH2CH(CH3)CH3



P8-188
C(CH3)3










Preferred embodiments of the present invention are the following compounds I.A-1, I.A-2, I.A-3, I.A-4, I.B-1, I.B-2, I.B-3, I.B-4 and I.C-1, I.C-2, I.C-3, I.C-4. In these formulae, the substituents R2, R3, R6, R7 and R8 are independently as defined above or preferably defined herein:




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In particular with a view to their use, according to one embodiment, preference is given to the compounds of the formulae I.A-1, I.A-2, I.A-3, I.A-4, I.B-1, I.B-2, I.B-3, I.B-4 and I.C-1, I.C-2, I.C-3, I.C-4 that are compiled in the Tables 1a to 3a. Each of the groups mentioned for a substituent in the tables is furthermore per se, independently of the combination in which it is mentioned, a particularly preferred aspect of the substituent in question.













TABLE B





No.
R2
R3
R7
R8







B-1
CH3
CH3
C6H5
CH3


B-2
OCH3
CH3
C6H5
CH3


B-3
CH2F
CH3
C6H5
CH3


B-4
CHF2
CH3
C6H5
CH3


B-5
CH3
OCH3
C6H5
CH3


B-6
OCH3
OCH3
C6H5
CH3


B-7
CH2F
OCH3
C6H5
CH3


B-8
CHF2
OCH3
C6H5
CH3


B-9
CH3
CH2F
C6H5
CH3


B-10
OCH3
CH2F
C6H5
CH3


B-11
CH2F
CH2F
C6H5
CH3


B-12
CHF2
CH2F
C6H5
CH3


B-13
CH3
CHF2
C6H5
CH3


B-14
OCH3
CHF2
C6H5
CH3


B-15
CH2F
CHF2
C6H5
CH3


B-16
CHF2
CHF2
C6H5
CH3


B-17
CH3
CH3
—CH2—C6H5
CH3


B-18
OCH3
CH3
—CH2—C6H5
CH3


B-19
CH2F
CH3
—CH2—C6H5
CH3


B-20
CHF2
CH3
—CH2—C6H5
CH3


B-21
CH3
OCH3
—CH2—C6H5
CH3


B-22
OCH3
OCH3
—CH2—C6H5
CH3


B-23
CH2F
OCH3
—CH2—C6H5
CH3


B-24
CHF2
OCH3
—CH2—C6H5
CH3


B-25
CH3
CH2F
—CH2—C6H5
CH3


B-26
OCH3
CH2F
—CH2—C6H5
CH3


B-27
CH2F
CH2F
—CH2—C6H5
CH3


B-28
CHF2
CH2F
—CH2—C6H5
CH3


B-29
CH3
CHF2
—CH2—C6H5
CH3


B-30
OCH3
CHF2
—CH2—C6H5
CH3


B-31
CH2F
CHF2
—CH2—C6H5
CH3


B-32
CHF2
CHF2
—CH2—C6H5
CH3


B-33
CH3
CH3
C6H5
CH(CH3)2


B-34
OCH3
CH3
C6H5
CH(CH3)2


B-35
CH2F
CH3
C6H5
CH(CH3)2


B-36
CHF2
CH3
C6H5
CH(CH3)2


B-37
CH3
OCH3
C6H5
CH(CH3)2


B-38
OCH3
OCH3
C6H5
CH(CH3)2


B-39
CH2F
OCH3
C6H5
CH(CH3)2


B-40
CHF2
OCH3
C6H5
CH(CH3)2


B-41
CH3
CH2F
C6H5
CH(CH3)2


B-42
OCH3
CH2F
C6H5
CH(CH3)2


B-43
CH2F
CH2F
C6H5
CH(CH3)2


B-44
CHF2
CH2F
C6H5
CH(CH3)2


B-45
CH3
CHF2
C6H5
CH(CH3)2


B-46
OCH3
CHF2
C6H5
CH(CH3)2


B-47
CH2F
CHF2
C6H5
CH(CH3)2


B-48
CHF2
CHF2
C6H5
CH(CH3)2


B-49
CH3
CH3
—CH2—C6H5
CH(CH3)2


B-50
OCH3
CH3
—CH2—C6H5
CH(CH3)2


B-51
CH2F
CH3
—CH2—C6H5
CH(CH3)2


B-52
CHF2
CH3
—CH2—C6H5
CH(CH3)2


B-53
CH3
OCH3
—CH2—C6H5
CH(CH3)2


B-54
OCH3
OCH3
—CH2—C6H5
CH(CH3)2


B-55
CH2F
OCH3
—CH2—C6H5
CH(CH3)2


B-56
CHF2
OCH3
—CH2—C6H5
CH(CH3)2


B-57
CH3
CH2F
—CH2—C6H5
CH(CH3)2


B-58
OCH3
CH2F
—CH2—C6H5
CH(CH3)2


B-59
CH2F
CH2F
—CH2—C6H5
CH(CH3)2


B-60
CHF2
CH2F
—CH2—C6H5
CH(CH3)2


B-61
CH3
CHF2
—CH2—C6H5
CH(CH3)2


B-62
OCH3
CHF2
—CH2—C6H5
CH(CH3)2


B-63
CH2F
CHF2
—CH2—C6H5
CH(CH3)2


B-64
CHF2
CHF2
—CH2—C6H5
CH(CH3)2


B-65
CH3
CH3
C6H5
C(CH3)3


B-66
OCH3
CH3
C6H5
C(CH3)3


B-67
CH2F
CH3
C6H5
C(CH3)3


B-68
CHF2
CH3
C6H5
C(CH3)3


B-69
CH3
OCH3
C6H5
C(CH3)3


B-70
OCH3
OCH3
C6H5
C(CH3)3


B-71
CH2F
OCH3
C6H5
C(CH3)3


B-72
CHF2
OCH3
C6H5
C(CH3)3


B-73
CH3
CH2F
C6H5
C(CH3)3


B-74
OCH3
CH2F
C6H5
C(CH3)3


B-75
CH2F
CH2F
C6H5
C(CH3)3


B-76
CHF2
CH2F
C6H5
C(CH3)3


B-77
CH3
CHF2
C6H5
C(CH3)3


B-78
OCH3
CHF2
C6H5
C(CH3)3


B-79
CH2F
CHF2
C6H5
C(CH3)3


B-80
CHF2
CHF2
C6H5
C(CH3)3


B-81
CH3
CH3
—CH2—C6H5
C(CH3)3


B-82
OCH3
CH3
—CH2—C6H5
C(CH3)3


B-83
CH2F
CH3
—CH2—C6H5
C(CH3)3


B-84
CHF2
CH3
—CH2—C6H5
C(CH3)3


B-85
CH3
OCH3
—CH2—C6H5
C(CH3)3


B-86
OCH3
OCH3
—CH2—C6H5
C(CH3)3


B-87
CH2F
OCH3
—CH2—C6H5
C(CH3)3


B-88
CHF2
OCH3
—CH2—C6H5
C(CH3)3


B-89
CH3
CH2F
—CH2—C6H5
C(CH3)3


B-90
OCH3
CH2F
—CH2—C6H5
C(CH3)3


B-91
CH2F
CH2F
—CH2—C6H5
C(CH3)3


B-92
CHF2
CH2F
—CH2—C6H5
C(CH3)3


B-93
CH3
CHF2
—CH2—C6H5
C(CH3)3


B-94
OCH3
CHF2
—CH2—C6H5
C(CH3)3


B-95
CH2F
CHF2
—CH2—C6H5
C(CH3)3


B-96
CHF2
CHF2
—CH2—C6H5
C(CH3)3


B-97
CH3
CH3
C6H5
—CH2—CH(CH3)2


B-98
OCH3
CH3
C6H5
—CH2—CH(CH3)2


B-99
CH2F
CH3
C6H5
—CH2—CH(CH3)2


B-100
CHF2
CH3
C6H5
—CH2—CH(CH3)2


B-101
CH3
OCH3
C6H5
—CH2—CH(CH3)2


B-102
OCH3
OCH3
C6H5
—CH2—CH(CH3)2


B-103
CH2F
OCH3
C6H5
—CH2—CH(CH3)2


B-104
CHF2
OCH3
C6H5
—CH2—CH(CH3)2


B-105
CH3
CH2F
C6H5
—CH2—CH(CH3)2


B-106
OCH3
CH2F
C6H5
—CH2—CH(CH3)2


B-107
CH2F
CH2F
C6H5
—CH2—CH(CH3)2


B-108
CHF2
CH2F
C6H5
—CH2—CH(CH3)2


B-109
CH3
CHF2
C6H5
—CH2—CH(CH3)2


B-110
OCH3
CHF2
C6H5
—CH2—CH(CH3)2


B-111
CH2F
CHF2
C6H5
—CH2—CH(CH3)2


B-112
CHF2
CHF2
C6H5
—CH2—CH(CH3)2


B-113
CH3
CH3
—CH2—C6H5
—CH2—CH(CH3)2


B-114
OCH3
CH3
—CH2—C6H5
—CH2—CH(CH3)2


B-115
CH2F
CH3
—CH2—C6H5
—CH2—CH(CH3)2


B-116
CHF2
CH3
—CH2—C6H5
—CH2—CH(CH3)2


B-117
CH3
OCH3
—CH2—C6H5
—CH2—CH(CH3)2


B-118
OCH3
OCH3
—CH2—C6H5
—CH2—CH(CH3)2


B-119
CH2F
OCH3
—CH2—C6H5
—CH2—CH(CH3)2


B-120
CHF2
OCH3
—CH2—C6H5
—CH2—CH(CH3)2


B-121
CH3
CH2F
—CH2—C6H5
—CH2—CH(CH3)2


B-122
OCH3
CH2F
—CH2—C6H5
—CH2—CH(CH3)2


B-123
CH2F
CH2F
—CH2—C6H5
—CH2—CH(CH3)2


B-124
CHF2
CH2F
—CH2—C6H5
—CH2—CH(CH3)2


B-125
CH3
CHF2
—CH2—C6H5
—CH2—CH(CH3)2


B-126
OCH3
CHF2
—CH2—C6H5
—CH2—CH(CH3)2


B-127
CH2F
CHF2
—CH2—C6H5
—CH2—CH(CH3)2


B-128
CHF2
CHF2
—CH2—C6H5
—CH2—CH(CH3)2


B-129
CH3
CH3
C6H5
CH3


B-130
CH2F
CH3
C6H5
CH3


B-131
OCH3
CH3
C6H5
CH3


B-132
CH3
CH2F
C6H5
CH3


B-133
CH2F
CH2F
C6H5
CH3


B-134
OCH3
CH2F
C6H5
CH3


B-135
CH3
CHF2
C6H5
CH3


B-136
CH2F
CHF2
C6H5
CH3


B-137
OCH3
CHF2
C6H5
CH3


B-138
CH3
CF3
C6H5
CH3


B-139
CH2F
CF3
C6H5
CH3


B-140
OCH3
CF3
C6H5
CH3


B-141
CH3
CH3
—CH2—C6H5
CH3


B-142
CH2F
CH3
—CH2—C6H5
CH3


B-143
OCH3
CH3
—CH2—C6H5
CH3


B-144
CH3
CH2F
—CH2—C6H5
CH3


B-145
CH2F
CH2F
—CH2—C6H5
CH3


B-146
OCH3
CH2F
—CH2—C6H5
CH3


B-147
CH3
CHF2
—CH2—C6H5
CH3


B-148
CH2F
CHF2
—CH2—C6H5
CH3


B-149
OCH3
CHF2
—CH2—C6H5
CH3


B-150
CH3
CF3
—CH2—C6H5
CH3


B-151
CH2F
CF3
—CH2—C6H5
CH3


B-152
OCH3
CF3
—CH2—C6H5
CH3


B-153
CH3
CH3
—CH2-(2-F—C6H4)
CH3


B-154
CH2F
CH3
—CH2-(2-F—C6H4)
CH3


B-155
OCH3
CH3
—CH2-(2-F—C6H4)
CH3


B-156
CH3
CH2F
—CH2-(2-F—C6H4)
CH3


B-157
CH2F
CH2F
—CH2-(2-F—C6H4)
CH3


B-158
OCH3
CH2F
—CH2-(2-F—C6H4)
CH3


B-159
CH3
CHF2
—CH2-(2-F—C6H4)
CH3


B-160
CH2F
CHF2
—CH2-(2-F—C6H4)
CH3


B-161
OCH3
CHF2
—CH2-(2-F—C6H4)
CH3


B-162
CH3
CF3
—CH2-(2-F—C6H4)
CH3


B-163
CH2F
CF3
—CH2-(2-F—C6H4)
CH3


B-164
OCH3
CF3
—CH2-(2-F—C6H4)
CH3


B-165
CH3
CH3
—CH2-(3-F—C6H4)
CH3


B-166
CH2F
CH3
—CH2-(3-F—C6H4)
CH3


B-167
OCH3
CH3
—CH2-(3-F—C6H4)
CH3


B-168
CH3
CH2F
—CH2-(3-F—C6H4)
CH3


B-169
CH2F
CH2F
—CH2-(3-F—C6H4)
CH3


B-170
OCH3
CH2F
—CH2-(3-F—C6H4)
CH3


B-171
CH3
CHF2
—CH2-(3-F—C6H4)
CH3


B-172
CH2F
CHF2
—CH2-(3-F—C6H4)
CH3


B-173
OCH3
CHF2
—CH2-(3-F—C6H4)
CH3


B-174
CH3
CF3
—CH2-(3-F—C6H4)
CH3


B-175
CH2F
CF3
—CH2-(3-F—C6H4)
CH3


B-176
OCH3
CF3
—CH2-(3-F—C6H4)
CH3


B-177
CH3
CH3
—CH2-(4-F—C6H4)
CH3


B-178
CH2F
CH3
—CH2-(4-F—C6H4)
CH3


B-179
OCH3
CH3
—CH2-(4-F—C6H4)
CH3


B-180
CH3
CH2F
—CH2-(4-F—C6H4)
CH3


B-181
CH2F
CH2F
—CH2-(4-F—C6H4)
CH3


B-182
OCH3
CH2F
—CH2-(4-F—C6H4)
CH3


B-183
CH3
CHF2
—CH2-(4-F—C6H4)
CH3


B-184
CH2F
CHF2
—CH2-(4-F—C6H4)
CH3


B-185
OCH3
CHF2
—CH2-(4-F—C6H4)
CH3


B-186
CH3
CF3
—CH2-(4-F—C6H4)
CH3


B-187
CH2F
CF3
—CH2-(4-F—C6H4)
CH3


B-188
OCH3
CF3
—CH2-(4-F—C6H4)
CH3


B-189
CH3
CH3
—CH2-(2,4-F2—C6H3)
CH3


B-190
CH2F
CH3
—CH2-(2,4-F2—C6H3)
CH3


B-191
OCH3
CH3
—CH2-(2,4-F2—C6H3)
CH3


B-192
CH3
CH2F
—CH2-(2,4-F2—C6H3)
CH3


B-193
CH2F
CH2F
—CH2-(2,4-F2—C6H3)
CH3


B-194
OCH3
CH2F
—CH2-(2,4-F2—C6H3)
CH3


B-195
CH3
CHF2
—CH2-(2,4-F2—C6H3)
CH3


B-196
CH2F
CHF2
—CH2-(2,4-F2—C6H3)
CH3


B-197
OCH3
CHF2
—CH2-(2,4-F2—C6H3)
CH3


B-198
CH3
CF3
—CH2-(2,4-F2—C6H3)
CH3


B-199
CH2F
CF3
—CH2-(2,4-F2—C6H3)
CH3


B-200
OCH3
CF3
—CH2-(2,4-F2—C6H3)
CH3


B-201
CH3
CH3
—CH2-(2-Cl—C6H4)
CH3


B-202
CH2F
CH3
—CH2-(2-Cl—C6H4)
CH3


B-203
OCH3
CH3
—CH2-(2-Cl—C6H4)
CH3


B-204
CH3
CH2F
—CH2-(2-Cl—C6H4)
CH3


B-205
CH2F
CH2F
—CH2-(2-Cl—C6H4)
CH3


B-206
OCH3
CH2F
—CH2-(2-Cl—C6H4)
CH3


B-207
CH3
CHF2
—CH2-(2-Cl—C6H4)
CH3


B-208
CH2F
CHF2
—CH2-(2-Cl—C6H4)
CH3


B-209
OCH3
CHF2
—CH2-(2-Cl—C6H4)
CH3


B-210
CH3
CF3
—CH2-(2-Cl—C6H4)
CH3


B-211
CH2F
CF3
—CH2-(2-Cl—C6H4)
CH3


B-212
OCH3
CF3
—CH2-(2-Cl—C6H4)
CH3


B-213
CH3
CH3
—CH2-(3-Cl—C6H4)
CH3


B-214
CH2F
CH3
—CH2-(3-Cl—C6H4)
CH3


B-215
OCH3
CH3
—CH2-(3-Cl—C6H4)
CH3


B-216
CH3
CH2F
—CH2-(3-Cl—C6H4)
CH3


B-217
CH2F
CH2F
—CH2-(3-Cl—C6H4)
CH3


B-218
OCH3
CH2F
—CH2-(3-Cl—C6H4)
CH3


B-219
CH3
CHF2
—CH2-(3-Cl—C6H4)
CH3


B-220
CH2F
CHF2
—CH2-(3-Cl—C6H4)
CH3


B-221
OCH3
CHF2
—CH2-(3-Cl—C6H4)
CH3


B-222
CH3
CF3
—CH2-(3-Cl—C6H4)
CH3


B-223
CH2F
CF3
—CH2-(3-Cl—C6H4)
CH3


B-224
OCH3
CF3
—CH2-(3-Cl—C6H4)
CH3


B-225
CH3
CH3
—CH2-(4-Cl—C6H4)
CH3


B-226
CH2F
CH3
—CH2-(4-Cl—C6H4)
CH3


B-227
OCH3
CH3
—CH2-(4-Cl—C6H4)
CH3


B-228
CH3
CH2F
—CH2-(4-Cl—C6H4)
CH3


B-229
CH2F
CH2F
—CH2-(4-Cl—C6H4)
CH3


B-230
OCH3
CH2F
—CH2-(4-Cl—C6H4)
CH3


B-231
CH3
CHF2
—CH2-(4-Cl—C6H4)
CH3


B-232
CH2F
CHF2
—CH2-(4-Cl—C6H4)
CH3


B-233
OCH3
CHF2
—CH2-(4-Cl—C6H4)
CH3


B-234
CH3
CF3
—CH2-(4-Cl—C6H4)
CH3


B-235
CH2F
CF3
—CH2-(4-Cl—C6H4)
CH3


B-236
OCH3
CF3
—CH2-(4-Cl—C6H4)
CH3


B-237
CH3
CH3
—CH2-(2,4-Cl2—C6H3)
CH3


B-238
CH2F
CH3
—CH2-(2,4-Cl2—C6H3)
CH3


B-239
OCH3
CH3
—CH2-(2,4-Cl2—C6H3)
CH3


B-240
CH3
CH2F
—CH2-(2,4-Cl2—C6H3)
CH3


B-241
CH2F
CH2F
—CH2-(2,4-Cl2—C6H3)
CH3


B-242
OCH3
CH2F
—CH2-(2,4-Cl2—C6H3)
CH3


B-243
CH3
CHF2
—CH2-(2,4-Cl2—C6H3)
CH3


B-244
CH2F
CHF2
—CH2-(2,4-Cl2—C6H3)
CH3


B-245
OCH3
CHF2
—CH2-(2,4-Cl2—C6H3)
CH3


B-246
CH3
CF3
—CH2-(2,4-Cl2—C6H3)
CH3


B-247
CH2F
CF3
—CH2-(2,4-Cl2—C6H3)
CH3


B-248
OCH3
CF3
—CH2-(2,4-Cl2—C6H3)
CH3


B-249
CH3
CH3
—CH2—CH2—C6H5
CH3


B-250
CH2F
CH3
—CH2—CH2—C6H5
CH3


B-251
OCH3
CH3
—CH2—CH2—C6H5
CH3


B-252
CH3
CH2F
—CH2—CH2—C6H5
CH3


B-253
CH2F
CH2F
—CH2—CH2—C6H5
CH3


B-254
OCH3
CH2F
—CH2—CH2—C6H5
CH3


B-255
CH3
CHF2
—CH2—CH2—C6H5
CH3


B-256
CH2F
CHF2
—CH2—CH2—C6H5
CH3


B-257
OCH3
CHF2
—CH2—CH2—C6H5
CH3


B-258
CH3
CF3
—CH2—CH2—C6H5
CH3


B-259
CH2F
CF3
—CH2—CH2—C6H5
CH3


B-260
OCH3
CF3
—CH2—CH2—C6H5
CH3


B-261
CH3
CH3
C6H5
CH2—CH3


B-262
CH2F
CH3
C6H5
CH2—CH3


B-263
OCH3
CH3
C6H5
CH2—CH3


B-264
CH3
CH2F
C6H5
CH2—CH3


B-265
CH2F
CH2F
C6H5
CH2—CH3


B-266
OCH3
CH2F
C6H5
CH2—CH3


B-267
CH3
CHF2
C6H5
CH2—CH3


B-268
CH2F
CHF2
C6H5
CH2—CH3


B-269
OCH3
CHF2
C6H5
CH2—CH3


B-270
CH3
CF3
C6H5
CH2—CH3


B-271
CH2F
CF3
C6H5
CH2—CH3


B-272
OCH3
CF3
C6H5
CH2—CH3


B-273
CH3
CH3
—CH2—C6H5
CH2—CH3


B-274
CH2F
CH3
—CH2—C6H5
CH2—CH3


B-275
OCH3
CH3
—CH2—C6H5
CH2—CH3


B-276
CH3
CH2F
—CH2—C6H5
CH2—CH3


B-277
CH2F
CH2F
—CH2—C6H5
CH2—CH3


B-278
OCH3
CH2F
—CH2—C6H5
CH2—CH3


B-279
CH3
CHF2
—CH2—C6H5
CH2—CH3


B-280
CH2F
CHF2
—CH2—C6H5
CH2—CH3


B-281
OCH3
CHF2
—CH2—C6H5
CH2—CH3


B-282
CH3
CF3
—CH2—C6H5
CH2—CH3


B-283
CH2F
CF3
—CH2—C6H5
CH2—CH3


B-284
OCH3
CF3
—CH2—C6H5
CH2—CH3


B-285
CH3
CH3
—CH2-(2-F—C6H4)
CH2—CH3


B-286
CH2F
CH3
—CH2-(2-F—C6H4)
CH2—CH3


B-287
OCH3
CH3
—CH2-(2-F—C6H4)
CH2—CH3


B-288
CH3
CH2F
—CH2-(2-F—C6H4)
CH2—CH3


B-289
CH2F
CH2F
—CH2-(2-F—C6H4)
CH2—CH3


B-290
OCH3
CH2F
—CH2-(2-F—C6H4)
CH2—CH3


B-291
CH3
CHF2
—CH2-(2-F—C6H4)
CH2—CH3


B-292
CH2F
CHF2
—CH2-(2-F—C6H4)
CH2—CH3


B-293
OCH3
CHF2
—CH2-(2-F—C6H4)
CH2—CH3


B-294
CH3
CF3
—CH2-(2-F—C6H4)
CH2—CH3


B-295
CH2F
CF3
—CH2-(2-F—C6H4)
CH2—CH3


B-296
OCH3
CF3
—CH2-(2-F—C6H4)
CH2—CH3


B-297
CH3
CH3
—CH2-(3-F—C6H4)
CH2—CH3


B-298
CH2F
CH3
—CH2-(3-F—C6H4)
CH2—CH3


B-299
OCH3
CH3
—CH2-(3-F—C6H4)
CH2—CH3


B-300
CH3
CH2F
—CH2-(3-F—C6H4)
CH2—CH3


B-301
CH2F
CH2F
—CH2-(3-F—C6H4)
CH2—CH3


B-302
OCH3
CH2F
—CH2-(3-F—C6H4)
CH2—CH3


B-303
CH3
CHF2
—CH2-(3-F—C6H4)
CH2—CH3


B-304
CH2F
CHF2
—CH2-(3-F—C6H4)
CH2—CH3


B-305
OCH3
CHF2
—CH2-(3-F—C6H4)
CH2—CH3


B-306
CH3
CF3
—CH2-(3-F—C6H4)
CH2—CH3


B-307
CH2F
CF3
—CH2-(3-F—C6H4)
CH2—CH3


B-308
OCH3
CF3
—CH2-(3-F—C6H4)
CH2—CH3


B-309
CH3
CH3
—CH2-(4-F—C6H4)
CH2—CH3


B-310
CH2F
CH3
—CH2-(4-F—C6H4)
CH2—CH3


B-311
OCH3
CH3
—CH2-(4-F—C6H4)
CH2—CH3


B-312
CH3
CH2F
—CH2-(4-F—C6H4)
CH2—CH3


B-313
CH2F
CH2F
—CH2-(4-F—C6H4)
CH2—CH3


B-314
OCH3
CH2F
—CH2-(4-F—C6H4)
CH2—CH3


B-315
CH3
CHF2
—CH2-(4-F—C6H4)
CH2—CH3


B-316
CH2F
CHF2
—CH2-(4-F—C6H4)
CH2—CH3


B-317
OCH3
CHF2
—CH2-(4-F—C6H4)
CH2—CH3


B-318
CH3
CF3
—CH2-(4-F—C6H4)
CH2—CH3


B-319
CH2F
CF3
—CH2-(4-F—C6H4)
CH2—CH3


B-320
OCH3
CF3
—CH2-(4-F—C6H4)
CH2—CH3


B-321
CH3
CH3
—CH2-(2,4-F2—C6H3)
CH2—CH3


B-322
CH2F
CH3
—CH2-(2,4-F2—C6H3)
CH2—CH3


B-323
OCH3
CH3
—CH2-(2,4-F2—C6H3)
CH2—CH3


B-324
CH3
CH2F
—CH2-(2,4-F2—C6H3)
CH2—CH3


B-325
CH2F
CH2F
—CH2-(2,4-F2—C6H3)
CH2—CH3


B-326
OCH3
CH2F
—CH2-(2,4-F2—C6H3)
CH2—CH3


B-327
CH3
CHF2
—CH2-(2,4-F2—C6H3)
CH2—CH3


B-328
CH2F
CHF2
—CH2-(2,4-F2—C6H3)
CH2—CH3


B-329
OCH3
CHF2
—CH2-(2,4-F2—C6H3)
CH2—CH3


B-330
CH3
CF3
—CH2-(2,4-F2—C6H3)
CH2—CH3


B-331
CH2F
CF3
—CH2-(2,4-F2—C6H3)
CH2—CH3


B-332
OCH3
CF3
—CH2-(2,4-F2—C6H3)
CH2—CH3


B-333
CH3
CH3
—CH2-(2-Cl—C6H4)
CH2—CH3


B-334
CH2F
CH3
—CH2-(2-Cl—C6H4)
CH2—CH3


B-335
OCH3
CH3
—CH2-(2-Cl—C6H4)
CH2—CH3


B-336
CH3
CH2F
—CH2-(2-Cl—C6H4)
CH2—CH3


B-337
CH2F
CH2F
—CH2-(2-Cl—C6H4)
CH2—CH3


B-338
OCH3
CH2F
—CH2-(2-Cl—C6H4)
CH2—CH3


B-339
CH3
CHF2
—CH2-(2-Cl—C6H4)
CH2—CH3


B-340
CH2F
CHF2
—CH2-(2-Cl—C6H4)
CH2—CH3


B-341
OCH3
CHF2
—CH2-(2-Cl—C6H4)
CH2—CH3


B-342
CH3
CF3
—CH2-(2-Cl—C6H4)
CH2—CH3


B-343
CH2F
CF3
—CH2-(2-Cl—C6H4)
CH2—CH3


B-344
OCH3
CF3
—CH2-(2-Cl—C6H4)
CH2—CH3


B-345
CH3
CH3
—CH2-(3-Cl—C6H4)
CH2—CH3


B-346
CH2F
CH3
—CH2-(3-Cl—C6H4)
CH2—CH3


B-347
OCH3
CH3
—CH2-(3-Cl—C6H4)
CH2—CH3


B-348
CH3
CH2F
—CH2-(3-Cl—C6H4)
CH2—CH3


B-349
CH2F
CH2F
—CH2-(3-Cl—C6H4)
CH2—CH3


B-350
OCH3
CH2F
—CH2-(3-Cl—C6H4)
CH2—CH3


B-351
CH3
CHF2
—CH2-(3-Cl—C6H4)
CH2—CH3


B-352
CH2F
CHF2
—CH2-(3-Cl—C6H4)
CH2—CH3


B-353
OCH3
CHF2
—CH2-(3-Cl—C6H4)
CH2—CH3


B-354
CH3
CF3
—CH2-(3-Cl—C6H4)
CH2—CH3


B-355
CH2F
CF3
—CH2-(3-Cl—C6H4)
CH2—CH3


B-356
OCH3
CF3
—CH2-(3-Cl—C6H4)
CH2—CH3


B-357
CH3
CH3
—CH2-(4-Cl—C6H4)
CH2—CH3


B-358
CH2F
CH3
—CH2-(4-Cl—C6H4)
CH2—CH3


B-359
OCH3
CH3
—CH2-(4-Cl—C6H4)
CH2—CH3


B-360
CH3
CH2F
—CH2-(4-Cl—C6H4)
CH2—CH3


B-361
CH2F
CH2F
—CH2-(4-Cl—C6H4)
CH2—CH3


B-362
OCH3
CH2F
—CH2-(4-Cl—C6H4)
CH2—CH3


B-363
CH3
CHF2
—CH2-(4-Cl—C6H4)
CH2—CH3


B-364
CH2F
CHF2
—CH2-(4-Cl—C6H4)
CH2—CH3


B-365
OCH3
CHF2
—CH2-(4-Cl—C6H4)
CH2—CH3


B-366
CH3
CF3
—CH2-(4-Cl—C6H4)
CH2—CH3


B-367
CH2F
CF3
—CH2-(4-Cl—C6H4)
CH2—CH3


B-368
OCH3
CF3
—CH2-(4-Cl—C6H4)
CH2—CH3


B-369
CH3
CH3
—CH2-(2,4-Cl2—C6H3)
CH2—CH3


B-370
CH2F
CH3
—CH2-(2,4-Cl2—C6H3)
CH2—CH3


B-371
OCH3
CH3
—CH2-(2,4-Cl2—C6H3)
CH2—CH3


B-372
CH3
CH2F
—CH2-(2,4-Cl2—C6H3)
CH2—CH3


B-373
CH2F
CH2F
—CH2-(2,4-Cl2—C6H3)
CH2—CH3


B-374
OCH3
CH2F
—CH2-(2,4-Cl2—C6H3)
CH2—CH3


B-375
CH3
CHF2
—CH2-(2,4-Cl2—C6H3)
CH2—CH3


B-376
CH2F
CHF2
—CH2-(2,4-Cl2—C6H3)
CH2—CH3


B-377
OCH3
CHF2
—CH2-(2,4-Cl2—C6H3)
CH2—CH3


B-378
CH3
CF3
—CH2-(2,4-Cl2—C6H3)
CH2—CH3


B-379
CH2F
CF3
—CH2-(2,4-Cl2—C6H3)
CH2—CH3


B-380
OCH3
CF3
—CH2-(2,4-Cl2—C6H3)
CH2—CH3


B-381
CH3
CH3
—CH2—CH2—C6H5
CH2—CH3


B-382
CH2F
CH3
—CH2—CH2—C6H5
CH2—CH3


B-383
OCH3
CH3
—CH2—CH2—C6H5
CH2—CH3


B-384
CH3
CH2F
—CH2—CH2—C6H5
CH2—CH3


B-385
CH2F
CH2F
—CH2—CH2—C6H5
CH2—CH3


B-386
OCH3
CH2F
—CH2—CH2—C6H5
CH2—CH3


B-387
CH3
CHF2
—CH2—CH2—C6H5
CH2—CH3


B-388
CH2F
CHF2
—CH2—CH2—C6H5
CH2—CH3


B-389
OCH3
CHF2
—CH2—CH2—C6H5
CH2—CH3


B-390
CH3
CF3
—CH2—CH2—C6H5
CH2—CH3


B-391
CH2F
CF3
—CH2—CH2—C6H5
CH2—CH3


B-392
OCH3
CF3
—CH2—CH2—C6H5
CH2—CH3


B-393
CH3
CH3
C6H5
CH2—CH2—CH3


B-394
CH2F
CH3
C6H5
CH2—CH2—CH3


B-395
OCH3
CH3
C6H5
CH2—CH2—CH3


B-396
CH3
CH2F
C6H5
CH2—CH2—CH3


B-397
CH2F
CH2F
C6H5
CH2—CH2—CH3


B-398
OCH3
CH2F
C6H5
CH2—CH2—CH3


B-399
CH3
CHF2
C6H5
CH2—CH2—CH3


B-400
CH2F
CHF2
C6H5
CH2—CH2—CH3


B-401
OCH3
CHF2
C6H5
CH2—CH2—CH3


B-402
CH3
CF3
C6H5
CH2—CH2—CH3


B-403
CH2F
CF3
C6H5
CH2—CH2—CH3


B-404
OCH3
CF3
C6H5
CH2—CH2—CH3


B-405
CH3
CH3
—CH2—C6H5
CH2—CH2—CH3


B-406
CH2F
CH3
—CH2—C6H5
CH2—CH2—CH3


B-407
OCH3
CH3
—CH2—C6H5
CH2—CH2—CH3


B-408
CH3
CH2F
—CH2—C6H5
CH2—CH2—CH3


B-409
CH2F
CH2F
—CH2—C6H5
CH2—CH2—CH3


B-410
OCH3
CH2F
—CH2—C6H5
CH2—CH2—CH3


B-411
CH3
CHF2
—CH2—C6H5
CH2—CH2—CH3


B-412
CH2F
CHF2
—CH2—C6H5
CH2—CH2—CH3


B-413
OCH3
CHF2
—CH2—C6H5
CH2—CH2—CH3


B-414
CH3
CF3
—CH2—C6H5
CH2—CH2—CH3


B-415
CH2F
CF3
—CH2—C6H5
CH2—CH2—CH3


B-416
OCH3
CF3
—CH2—C6H5
CH2—CH2—CH3


B-417
CH3
CH3
—CH2-(2-F—C6H4)
CH2—CH2—CH3


B-418
CH2F
CH3
—CH2-(2-F—C6H4)
CH2—CH2—CH3


B-419
OCH3
CH3
—CH2-(2-F—C6H4)
CH2—CH2—CH3


B-420
CH3
CH2F
—CH2-(2-F—C6H4)
CH2—CH2—CH3


B-421
CH2F
CH2F
—CH2-(2-F—C6H4)
CH2—CH2—CH3


B-422
OCH3
CH2F
—CH2-(2-F—C6H4)
CH2—CH2—CH3


B-423
CH3
CHF2
—CH2-(2-F—C6H4)
CH2—CH2—CH3


B-424
CH2F
CHF2
—CH2-(2-F—C6H4)
CH2—CH2—CH3


B-425
OCH3
CHF2
—CH2-(2-F—C6H4)
CH2—CH2—CH3


B-426
CH3
CF3
—CH2-(2-F—C6H4)
CH2—CH2—CH3


B-427
CH2F
CF3
—CH2-(2-F—C6H4)
CH2—CH2—CH3


B-428
OCH3
CF3
—CH2-(2-F—C6H4)
CH2—CH2—CH3


B-429
CH3
CH3
—CH2-(3-F—C6H4)
CH2—CH2—CH3


B-430
CH2F
CH3
—CH2-(3-F—C6H4)
CH2—CH2—CH3


B-431
OCH3
CH3
—CH2-(3-F—C6H4)
CH2—CH2—CH3


B-432
CH3
CH2F
—CH2-(3-F—C6H4)
CH2—CH2—CH3


B-433
CH2F
CH2F
—CH2-(3-F—C6H4)
CH2—CH2—CH3


B-434
OCH3
CH2F
—CH2-(3-F—C6H4)
CH2—CH2—CH3


B-435
CH3
CHF2
—CH2-(3-F—C6H4)
CH2—CH2—CH3


B-436
CH2F
CHF2
—CH2-(3-F—C6H4)
CH2—CH2—CH3


B-437
OCH3
CHF2
—CH2-(3-F—C6H4)
CH2—CH2—CH3


B-438
CH3
CF3
—CH2-(3-F—C6H4)
CH2—CH2—CH3


B-439
CH2F
CF3
—CH2-(3-F—C6H4)
CH2—CH2—CH3


B-440
OCH3
CF3
—CH2-(3-F—C6H4)
CH2—CH2—CH3


B-441
CH3
CH3
—CH2-(4-F—C6H4)
CH2—CH2—CH3


B-442
CH2F
CH3
—CH2-(4-F—C6H4)
CH2—CH2—CH3


B-443
OCH3
CH3
—CH2-(4-F—C6H4)
CH2—CH2—CH3


B-444
CH3
CH2F
—CH2-(4-F—C6H4)
CH2—CH2—CH3


B-445
CH2F
CH2F
—CH2-(4-F—C6H4)
CH2—CH2—CH3


B-446
OCH3
CH2F
—CH2-(4-F—C6H4)
CH2—CH2—CH3


B-447
CH3
CHF2
—CH2-(4-F—C6H4)
CH2—CH2—CH3


B-448
CH2F
CHF2
—CH2-(4-F—C6H4)
CH2—CH2—CH3


B-449
OCH3
CHF2
—CH2-(4-F—C6H4)
CH2—CH2—CH3


B-450
CH3
CF3
—CH2-(4-F—C6H4)
CH2—CH2—CH3


B-451
CH2F
CF3
—CH2-(4-F—C6H4)
CH2—CH2—CH3


B-452
OCH3
CF3
—CH2-(4-F—C6H4)
CH2—CH2—CH3


B-453
CH3
CH3
—CH2-(2,4-F2—C6H3)
CH2—CH2—CH3


B-454
CH2F
CH3
—CH2-(2,4-F2—C6H3)
CH2—CH2—CH3


B-455
OCH3
CH3
—CH2-(2,4-F2—C6H3)
CH2—CH2—CH3


B-456
CH3
CH2F
—CH2-(2,4-F2—C6H3)
CH2—CH2—CH3


B-457
CH2F
CH2F
—CH2-(2,4-F2—C6H3)
CH2—CH2—CH3


B-458
OCH3
CH2F
—CH2-(2,4-F2—C6H3)
CH2—CH2—CH3


B-459
CH3
CHF2
—CH2-(2,4-F2—C6H3)
CH2—CH2—CH3


B-460
CH2F
CHF2
—CH2-(2,4-F2—C6H3)
CH2—CH2—CH3


B-461
OCH3
CHF2
—CH2-(2,4-F2—C6H3)
CH2—CH2—CH3


B-462
CH3
CF3
—CH2-(2,4-F2—C6H3)
CH2—CH2—CH3


B-463
CH2F
CF3
—CH2-(2,4-F2—C6H3)
CH2—CH2—CH3


B-464
OCH3
CF3
—CH2-(2,4-F2—C6H3)
CH2—CH2—CH3


B-465
CH3
CH3
—CH2-(2-Cl—C6H4)
CH2—CH2—CH3


B-466
CH2F
CH3
—CH2-(2-Cl—C6H4)
CH2—CH2—CH3


B-467
OCH3
CH3
—CH2-(2-Cl—C6H4)
CH2—CH2—CH3


B-468
CH3
CH2F
—CH2-(2-Cl—C6H4)
CH2—CH2—CH3


B-469
CH2F
CH2F
—CH2-(2-Cl—C6H4)
CH2—CH2—CH3


B-470
OCH3
CH2F
—CH2-(2-Cl—C6H4)
CH2—CH2—CH3


B-471
CH3
CHF2
—CH2-(2-Cl—C6H4)
CH2—CH2—CH3


B-472
CH2F
CHF2
—CH2-(2-Cl—C6H4)
CH2—CH2—CH3


B-473
OCH3
CHF2
—CH2-(2-Cl—C6H4)
CH2—CH2—CH3


B-474
CH3
CF3
—CH2-(2-Cl—C6H4)
CH2—CH2—CH3


B-475
CH2F
CF3
—CH2-(2-Cl—C6H4)
CH2—CH2—CH3


B-476
OCH3
CF3
—CH2-(2-Cl—C6H4)
CH2—CH2—CH3


B-477
CH3
CH3
—CH2-(3-Cl—C6H4)
CH2—CH2—CH3


B-478
CH2F
CH3
—CH2-(3-Cl—C6H4)
CH2—CH2—CH3


B-479
OCH3
CH3
—CH2-(3-Cl—C6H4)
CH2—CH2—CH3


B-480
CH3
CH2F
—CH2-(3-Cl—C6H4)
CH2—CH2—CH3


B-481
CH2F
CH2F
—CH2-(3-Cl—C6H4)
CH2—CH2—CH3


B-482
OCH3
CH2F
—CH2-(3-Cl—C6H4)
CH2—CH2—CH3


B-483
CH3
CHF2
—CH2-(3-Cl—C6H4)
CH2—CH2—CH3


B-484
CH2F
CHF2
—CH2-(3-Cl—C6H4)
CH2—CH2—CH3


B-485
OCH3
CHF2
—CH2-(3-Cl—C6H4)
CH2—CH2—CH3


B-486
CH3
CF3
—CH2-(3-Cl—C6H4)
CH2—CH2—CH3


B-487
CH2F
CF3
—CH2-(3-Cl—C6H4)
CH2—CH2—CH3


B-488
OCH3
CF3
—CH2-(3-Cl—C6H4)
CH2—CH2—CH3


B-489
CH3
CH3
—CH2-(4-Cl—C6H4)
CH2—CH2—CH3


B-490
CH2F
CH3
—CH2-(4-Cl—C6H4)
CH2—CH2—CH3


B-491
OCH3
CH3
—CH2-(4-Cl—C6H4)
CH2—CH2—CH3


B-492
CH3
CH2F
—CH2-(4-Cl—C6H4)
CH2—CH2—CH3


B-493
CH2F
CH2F
—CH2-(4-Cl—C6H4)
CH2—CH2—CH3


B-494
OCH3
CH2F
—CH2-(4-Cl—C6H4)
CH2—CH2—CH3


B-495
CH3
CHF2
—CH2-(4-Cl—C6H4)
CH2—CH2—CH3


B-496
CH2F
CHF2
—CH2-(4-Cl—C6H4)
CH2—CH2—CH3


B-497
OCH3
CHF2
—CH2-(4-Cl—C6H4)
CH2—CH2—CH3


B-498
CH3
CF3
—CH2-(4-Cl—C6H4)
CH2—CH2—CH3


B-499
CH2F
CF3
—CH2-(4-Cl—C6H4)
CH2—CH2—CH3


B-500
OCH3
CF3
—CH2-(4-Cl—C6H4)
CH2—CH2—CH3


B-501
CH3
CH3
—CH2-(2,4-Cl2—C6H3)
CH2—CH2—CH3


B-502
CH2F
CH3
—CH2-(2,4-Cl2—C6H3)
CH2—CH2—CH3


B-503
OCH3
CH3
—CH2-(2,4-Cl2—C6H3)
CH2—CH2—CH3


B-504
CH3
CH2F
—CH2-(2,4-Cl2—C6H3)
CH2—CH2—CH3


B-505
CH2F
CH2F
—CH2-(2,4-Cl2—C6H3)
CH2—CH2—CH3


B-506
OCH3
CH2F
—CH2-(2,4-Cl2—C6H3)
CH2—CH2—CH3


B-507
CH3
CHF2
—CH2-(2,4-Cl2—C6H3)
CH2—CH2—CH3


B-508
CH2F
CHF2
—CH2-(2,4-Cl2—C6H3)
CH2—CH2—CH3


B-509
OCH3
CHF2
—CH2-(2,4-Cl2—C6H3)
CH2—CH2—CH3


B-510
CH3
CF3
—CH2-(2,4-Cl2—C6H3)
CH2—CH2—CH3


B-511
CH2F
CF3
—CH2-(2,4-Cl2—C6H3)
CH2—CH2—CH3


B-512
OCH3
CF3
—CH2-(2,4-Cl2—C6H3)
CH2—CH2—CH3


B-513
CH3
CH3
—CH2—CH2—C6H5
CH2—CH2—CH3


B-514
CH2F
CH3
—CH2—CH2—C6H5
CH2—CH2—CH3


B-515
OCH3
CH3
—CH2—CH2—C6H5
CH2—CH2—CH3


B-516
CH3
CH2F
—CH2—CH2—C6H5
CH2—CH2—CH3


B-517
CH2F
CH2F
—CH2—CH2—C6H5
CH2—CH2—CH3


B-518
OCH3
CH2F
—CH2—CH2—C6H5
CH2—CH2—CH3


B-519
CH3
CHF2
—CH2—CH2—C6H5
CH2—CH2—CH3


B-520
CH2F
CHF2
—CH2—CH2—C6H5
CH2—CH2—CH3


B-521
OCH3
CHF2
—CH2—CH2—C6H5
CH2—CH2—CH3


B-522
CH3
CF3
—CH2—CH2—C6H5
CH2—CH2—CH3


B-523
CH2F
CF3
—CH2—CH2—C6H5
CH2—CH2—CH3


B-524
OCH3
CF3
—CH2—CH2—C6H5
CH2—CH2—CH3


B-525
CH3
CH3
C6H5
—CH(CH3)2


B-526
CH2F
CH3
C6H5
—CH(CH3)2


B-527
OCH3
CH3
C6H5
—CH(CH3)2


B-528
CH3
CH2F
C6H5
—CH(CH3)2


B-529
CH2F
CH2F
C6H5
—CH(CH3)2


B-530
OCH3
CH2F
C6H5
—CH(CH3)2


B-531
CH3
CHF2
C6H5
—CH(CH3)2


B-532
CH2F
CHF2
C6H5
—CH(CH3)2


B-533
OCH3
CHF2
C6H5
—CH(CH3)2


B-534
CH3
CF3
C6H5
—CH(CH3)2


B-535
CH2F
CF3
C6H5
—CH(CH3)2


B-536
OCH3
CF3
C6H5
—CH(CH3)2


B-537
CH3
CH3
—CH2—C6H5
—CH(CH3)2


B-538
CH2F
CH3
—CH2—C6H5
—CH(CH3)2


B-539
OCH3
CH3
—CH2—C6H5
—CH(CH3)2


B-540
CH3
CH2F
—CH2—C6H5
—CH(CH3)2


B-541
CH2F
CH2F
—CH2—C6H5
—CH(CH3)2


B-542
OCH3
CH2F
—CH2—C6H5
—CH(CH3)2


B-543
CH3
CHF2
—CH2—C6H5
—CH(CH3)2


B-544
CH2F
CHF2
—CH2—C6H5
—CH(CH3)2


B-545
OCH3
CHF2
—CH2—C6H5
—CH(CH3)2


B-546
CH3
CF3
—CH2—C6H5
—CH(CH3)2


B-547
CH2F
CF3
—CH2—C6H5
—CH(CH3)2


B-548
OCH3
CF3
—CH2—C6H5
—CH(CH3)2


B-549
CH3
CH3
—CH2-(2-F—C6H4)
—CH(CH3)2


B-550
CH2F
CH3
—CH2-(2-F—C6H4)
—CH(CH3)2


B-551
OCH3
CH3
—CH2-(2-F—C6H4)
—CH(CH3)2


B-552
CH3
CH2F
—CH2-(2-F—C6H4)
—CH(CH3)2


B-553
CH2F
CH2F
—CH2-(2-F—C6H4)
—CH(CH3)2


B-554
OCH3
CH2F
—CH2-(2-F—C6H4)
—CH(CH3)2


B-555
CH3
CHF2
—CH2-(2-F—C6H4)
—CH(CH3)2


B-556
CH2F
CHF2
—CH2-(2-F—C6H4)
—CH(CH3)2


B-557
OCH3
CHF2
—CH2-(2-F—C6H4)
—CH(CH3)2


B-558
CH3
CF3
—CH2-(2-F—C6H4)
—CH(CH3)2


B-559
CH2F
CF3
—CH2-(2-F—C6H4)
—CH(CH3)2


B-560
OCH3
CF3
—CH2-(2-F—C6H4)
—CH(CH3)2


B-561
CH3
CH3
—CH2-(3-F—C6H4)
—CH(CH3)2


B-562
CH2F
CH3
—CH2-(3-F—C6H4)
—CH(CH3)2


B-563
OCH3
CH3
—CH2-(3-F—C6H4)
—CH(CH3)2


B-564
CH3
CH2F
—CH2-(3-F—C6H4)
—CH(CH3)2


B-565
CH2F
CH2F
—CH2-(3-F—C6H4)
—CH(CH3)2


B-566
OCH3
CH2F
—CH2-(3-F—C6H4)
—CH(CH3)2


B-567
CH3
CHF2
—CH2-(3-F—C6H4)
—CH(CH3)2


B-568
CH2F
CHF2
—CH2-(3-F—C6H4)
—CH(CH3)2


B-569
OCH3
CHF2
—CH2-(3-F—C6H4)
—CH(CH3)2


B-570
CH3
CF3
—CH2-(3-F—C6H4)
—CH(CH3)2


B-571
CH2F
CF3
—CH2-(3-F—C6H4)
—CH(CH3)2


B-572
OCH3
CF3
—CH2-(3-F—C6H4)
—CH(CH3)2


B-573
CH3
CH3
—CH2-(4-F—C6H4)
—CH(CH3)2


B-574
CH2F
CH3
—CH2-(4-F—C6H4)
—CH(CH3)2


B-575
OCH3
CH3
—CH2-(4-F—C6H4)
—CH(CH3)2


B-576
CH3
CH2F
—CH2-(4-F—C6H4)
—CH(CH3)2


B-577
CH2F
CH2F
—CH2-(4-F—C6H4)
—CH(CH3)2


B-578
OCH3
CH2F
—CH2-(4-F—C6H4)
—CH(CH3)2


B-579
CH3
CHF2
—CH2-(4-F—C6H4)
—CH(CH3)2


B-580
CH2F
CHF2
—CH2-(4-F—C6H4)
—CH(CH3)2


B-581
OCH3
CHF2
—CH2-(4-F—C6H4)
—CH(CH3)2


B-582
CH3
CF3
—CH2-(4-F—C6H4)
—CH(CH3)2


B-583
CH2F
CF3
—CH2-(4-F—C6H4)
—CH(CH3)2


B-584
OCH3
CF3
—CH2-(4-F—C6H4)
—CH(CH3)2


B-585
CH3
CH3
—CH2-(2,4-F2—C6H3)
—CH(CH3)2


B-586
CH2F
CH3
—CH2-(2,4-F2—C6H3)
—CH(CH3)2


B-587
OCH3
CH3
—CH2-(2,4-F2—C6H3)
—CH(CH3)2


B-588
CH3
CH2F
—CH2-(2,4-F2—C6H3)
—CH(CH3)2


B-589
CH2F
CH2F
—CH2-(2,4-F2—C6H3)
—CH(CH3)2


B-590
OCH3
CH2F
—CH2-(2,4-F2—C6H3)
—CH(CH3)2


B-591
CH3
CHF2
—CH2-(2,4-F2—C6H3)
—CH(CH3)2


B-592
CH2F
CHF2
—CH2-(2,4-F2—C6H3)
—CH(CH3)2


B-593
OCH3
CHF2
—CH2-(2,4-F2—C6H3)
—CH(CH3)2


B-594
CH3
CF3
—CH2-(2,4-F2—C6H3)
—CH(CH3)2


B-595
CH2F
CF3
—CH2-(2,4-F2—C6H3)
—CH(CH3)2


B-596
OCH3
CF3
—CH2-(2,4-F2—C6H3)
—CH(CH3)2


B-597
CH3
CH3
—CH2-(2-Cl—C6H4)
—CH(CH3)2


B-598
CH2F
CH3
—CH2-(2-Cl—C6H4)
—CH(CH3)2


B-599
OCH3
CH3
—CH2-(2-Cl—C6H4)
—CH(CH3)2


B-600
CH3
CH2F
—CH2-(2-Cl—C6H4)
—CH(CH3)2


B-601
CH2F
CH2F
—CH2-(2-Cl—C6H4)
—CH(CH3)2


B-602
OCH3
CH2F
—CH2-(2-Cl—C6H4)
—CH(CH3)2


B-603
CH3
CHF2
—CH2-(2-Cl—C6H4)
—CH(CH3)2


B-604
CH2F
CHF2
—CH2-(2-Cl—C6H4)
—CH(CH3)2


B-605
OCH3
CHF2
—CH2-(2-Cl—C6H4)
—CH(CH3)2


B-606
CH3
CF3
—CH2-(2-Cl—C6H4)
—CH(CH3)2


B-607
CH2F
CF3
—CH2-(2-Cl—C6H4)
—CH(CH3)2


B-608
OCH3
CF3
—CH2-(2-Cl—C6H4)
—CH(CH3)2


B-609
CH3
CH3
—CH2-(3-Cl—C6H4)
—CH(CH3)2


B-610
CH2F
CH3
—CH2-(3-Cl—C6H4)
—CH(CH3)2


B-611
OCH3
CH3
—CH2-(3-Cl—C6H4)
—CH(CH3)2


B-612
CH3
CH2F
—CH2-(3-Cl—C6H4)
—CH(CH3)2


B-613
CH2F
CH2F
—CH2-(3-Cl—C6H4)
—CH(CH3)2


B-614
OCH3
CH2F
—CH2-(3-Cl—C6H4)
—CH(CH3)2


B-615
CH3
CHF2
—CH2-(3-Cl—C6H4)
—CH(CH3)2


B-616
CH2F
CHF2
—CH2-(3-Cl—C6H4)
—CH(CH3)2


B-617
OCH3
CHF2
—CH2-(3-Cl—C6H4)
—CH(CH3)2


B-618
CH3
CF3
—CH2-(3-Cl—C6H4)
—CH(CH3)2


B-619
CH2F
CF3
—CH2-(3-Cl—C6H4)
—CH(CH3)2


B-620
OCH3
CF3
—CH2-(3-Cl—C6H4)
—CH(CH3)2


B-621
CH3
CH3
—CH2-(4-Cl—C6H4)
—CH(CH3)2


B-622
CH2F
CH3
—CH2-(4-Cl—C6H4)
—CH(CH3)2


B-623
OCH3
CH3
—CH2-(4-Cl—C6H4)
—CH(CH3)2


B-624
CH3
CH2F
—CH2-(4-Cl—C6H4)
—CH(CH3)2


B-625
CH2F
CH2F
—CH2-(4-Cl—C6H4)
—CH(CH3)2


B-626
OCH3
CH2F
—CH2-(4-Cl—C6H4)
—CH(CH3)2


B-627
CH3
CHF2
—CH2-(4-Cl—C6H4)
—CH(CH3)2


B-628
CH2F
CHF2
—CH2-(4-Cl—C6H4)
—CH(CH3)2


B-629
OCH3
CHF2
—CH2-(4-Cl—C6H4)
—CH(CH3)2


B-630
CH3
CF3
—CH2-(4-Cl—C6H4)
—CH(CH3)2


B-631
CH2F
CF3
—CH2-(4-Cl—C6H4)
—CH(CH3)2


B-632
OCH3
CF3
—CH2-(4-Cl—C6H4)
—CH(CH3)2


B-633
CH3
CH3
—CH2-(2,4-Cl2—C6H3)
—CH(CH3)2


B-634
CH2F
CH3
—CH2-(2,4-Cl2—C6H3)
—CH(CH3)2


B-635
OCH3
CH3
—CH2-(2,4-Cl2—C6H3)
—CH(CH3)2


B-636
CH3
CH2F
—CH2-(2,4-Cl2—C6H3)
—CH(CH3)2


B-637
CH2F
CH2F
—CH2-(2,4-Cl2—C6H3)
—CH(CH3)2


B-638
OCH3
CH2F
—CH2-(2,4-Cl2—C6H3)
—CH(CH3)2


B-639
CH3
CHF2
—CH2-(2,4-Cl2—C6H3)
—CH(CH3)2


B-640
CH2F
CHF2
—CH2-(2,4-Cl2—C6H3)
—CH(CH3)2


B-641
OCH3
CHF2
—CH2-(2,4-Cl2—C6H3)
—CH(CH3)2


B-642
CH3
CF3
—CH2-(2,4-Cl2—C6H3)
—CH(CH3)2


B-643
CH2F
CF3
—CH2-(2,4-Cl2—C6H3)
—CH(CH3)2


B-644
OCH3
CF3
—CH2-(2,4-Cl2—C6H3)
—CH(CH3)2


B-645
CH3
CH3
—CH2—CH2—C6H5
—CH(CH3)2


B-646
CH2F
CH3
—CH2—CH2—C6H5
—CH(CH3)2


B-647
OCH3
CH3
—CH2—CH2—C6H5
—CH(CH3)2


B-648
CH3
CH2F
—CH2—CH2—C6H5
—CH(CH3)2


B-649
CH2F
CH2F
—CH2—CH2—C6H5
—CH(CH3)2


B-650
OCH3
CH2F
—CH2—CH2—C6H5
—CH(CH3)2


B-651
CH3
CHF2
—CH2—CH2—C6H5
—CH(CH3)2


B-652
CH2F
CHF2
—CH2—CH2—C6H5
—CH(CH3)2


B-653
OCH3
CHF2
—CH2—CH2—C6H5
—CH(CH3)2


B-654
CH3
CF3
—CH2—CH2—C6H5
—CH(CH3)2


B-655
CH2F
CF3
—CH2—CH2—C6H5
—CH(CH3)2


B-656
OCH3
CF3
—CH2—CH2—C6H5
—CH(CH3)2


B-657
CH3
CH3
C6H5
—(CH2)3—CH3


B-658
CH2F
CH3
C6H5
—(CH2)3—CH3


B-659
OCH3
CH3
C6H5
—(CH2)3—CH3


B-660
CH3
CH2F
C6H5
—(CH2)3—CH3


B-661
CH2F
CH2F
C6H5
—(CH2)3—CH3


B-662
OCH3
CH2F
C6H5
—(CH2)3—CH3


B-663
CH3
CHF2
C6H5
—(CH2)3—CH3


B-664
CH2F
CHF2
C6H5
—(CH2)3—CH3


B-665
OCH3
CHF2
C6H5
—(CH2)3—CH3


B-666
CH3
CF3
C6H5
—(CH2)3—CH3


B-667
CH2F
CF3
C6H5
—(CH2)3—CH3


B-668
OCH3
CF3
C6H5
—(CH2)3—CH3


B-669
CH3
CH3
—CH2—C6H5
—(CH2)3—CH3


B-670
CH2F
CH3
—CH2—C6H5
—(CH2)3—CH3


B-671
OCH3
CH3
—CH2—C6H5
—(CH2)3—CH3


B-672
CH3
CH2F
—CH2—C6H5
—(CH2)3—CH3


B-673
CH2F
CH2F
—CH2—C6H5
—(CH2)3—CH3


B-674
OCH3
CH2F
—CH2—C6H5
—(CH2)3—CH3


B-675
CH3
CHF2
—CH2—C6H5
—(CH2)3—CH3


B-676
CH2F
CHF2
—CH2—C6H5
—(CH2)3—CH3


B-677
OCH3
CHF2
—CH2—C6H5
—(CH2)3—CH3


B-678
CH3
CF3
—CH2—C6H5
—(CH2)3—CH3


B-679
CH2F
CF3
—CH2—C6H5
—(CH2)3—CH3


B-680
OCH3
CF3
—CH2—C6H5
—(CH2)3—CH3


B-681
CH3
CH3
—CH2-(2-F—C6H4)
—(CH2)3—CH3


B-682
CH2F
CH3
—CH2-(2-F—C6H4)
—(CH2)3—CH3


B-683
OCH3
CH3
—CH2-(2-F—C6H4)
—(CH2)3—CH3


B-684
CH3
CH2F
—CH2-(2-F—C6H4)
—(CH2)3—CH3


B-685
CH2F
CH2F
—CH2-(2-F—C6H4)
—(CH2)3—CH3


B-686
OCH3
CH2F
—CH2-(2-F—C6H4)
—(CH2)3—CH3


B-687
CH3
CHF2
—CH2-(2-F—C6H4)
—(CH2)3—CH3


B-688
CH2F
CHF2
—CH2-(2-F—C6H4)
—(CH2)3—CH3


B-689
OCH3
CHF2
—CH2-(2-F—C6H4)
—(CH2)3—CH3


B-690
CH3
CF3
—CH2-(2-F—C6H4)
—(CH2)3—CH3


B-691
CH2F
CF3
—CH2-(2-F—C6H4)
—(CH2)3—CH3


B-692
OCH3
CF3
—CH2-(2-F—C6H4)
—(CH2)3—CH3


B-693
CH3
CH3
—CH2-(3-F—C6H4)
—(CH2)3—CH3


B-694
CH2F
CH3
—CH2-(3-F—C6H4)
—(CH2)3—CH3


B-695
OCH3
CH3
—CH2-(3-F—C6H4)
—(CH2)3—CH3


B-696
CH3
CH2F
—CH2-(3-F—C6H4)
—(CH2)3—CH3


B-697
CH2F
CH2F
—CH2-(3-F—C6H4)
—(CH2)3—CH3


B-698
OCH3
CH2F
—CH2-(3-F—C6H4)
—(CH2)3—CH3


B-699
CH3
CHF2
—CH2-(3-F—C6H4)
—(CH2)3—CH3


B-700
CH2F
CHF2
—CH2-(3-F—C6H4)
—(CH2)3—CH3


B-701
OCH3
CHF2
—CH2-(3-F—C6H4)
—(CH2)3—CH3


B-702
CH3
CF3
—CH2-(3-F—C6H4)
—(CH2)3—CH3


B-703
CH2F
CF3
—CH2-(3-F—C6H4)
—(CH2)3—CH3


B-704
OCH3
CF3
—CH2-(3-F—C6H4)
—(CH2)3—CH3


B-705
CH3
CH3
—CH2-(4-F—C6H4)
—(CH2)3—CH3


B-706
CH2F
CH3
—CH2-(4-F—C6H4)
—(CH2)3—CH3


B-707
OCH3
CH3
—CH2-(4-F—C6H4)
—(CH2)3—CH3


B-708
CH3
CH2F
—CH2-(4-F—C6H4)
—(CH2)3—CH3


B-709
CH2F
CH2F
—CH2-(4-F—C6H4)
—(CH2)3—CH3


B-710
OCH3
CH2F
—CH2-(4-F—C6H4)
—(CH2)3—CH3


B-711
CH3
CHF2
—CH2-(4-F—C6H4)
—(CH2)3—CH3


B-712
CH2F
CHF2
—CH2-(4-F—C6H4)
—(CH2)3—CH3


B-713
OCH3
CHF2
—CH2-(4-F—C6H4)
—(CH2)3—CH3


B-714
CH3
CF3
—CH2-(4-F—C6H4)
—(CH2)3—CH3


B-715
CH2F
CF3
—CH2-(4-F—C6H4)
—(CH2)3—CH3


B-716
OCH3
CF3
—CH2-(4-F—C6H4)
—(CH2)3—CH3


B-717
CH3
CH3
—CH2-(2,4-F2—C6H3)
—(CH2)3—CH3


B-718
CH2F
CH3
—CH2-(2,4-F2—C6H3)
—(CH2)3—CH3


B-719
OCH3
CH3
—CH2-(2,4-F2—C6H3)
—(CH2)3—CH3


B-720
CH3
CH2F
—CH2-(2,4-F2—C6H3)
—(CH2)3—CH3


B-721
CH2F
CH2F
—CH2-(2,4-F2—C6H3)
—(CH2)3—CH3


B-722
OCH3
CH2F
—CH2-(2,4-F2—C6H3)
—(CH2)3—CH3


B-723
CH3
CHF2
—CH2-(2,4-F2—C6H3)
—(CH2)3—CH3


B-724
CH2F
CHF2
—CH2-(2,4-F2—C6H3)
—(CH2)3—CH3


B-725
OCH3
CHF2
—CH2-(2,4-F2—C6H3)
—(CH2)3—CH3


B-726
CH3
CF3
—CH2-(2,4-F2—C6H3)
—(CH2)3—CH3


B-727
CH2F
CF3
—CH2-(2,4-F2—C6H3)
—(CH2)3—CH3


B-728
OCH3
CF3
—CH2-(2,4-F2—C6H3)
—(CH2)3—CH3


B-729
CH3
CH3
—CH2-(2-Cl—C6H4)
—(CH2)3—CH3


B-730
CH2F
CH3
—CH2-(2-Cl—C6H4)
—(CH2)3—CH3


B-731
OCH3
CH3
—CH2-(2-Cl—C6H4)
—(CH2)3—CH3


B-732
CH3
CH2F
—CH2-(2-Cl—C6H4)
—(CH2)3—CH3


B-733
CH2F
CH2F
—CH2-(2-Cl—C6H4)
—(CH2)3—CH3


B-734
OCH3
CH2F
—CH2-(2-Cl—C6H4)
—(CH2)3—CH3


B-735
CH3
CHF2
—CH2-(2-Cl—C6H4)
—(CH2)3—CH3


B-736
CH2F
CHF2
—CH2-(2-Cl—C6H4)
—(CH2)3—CH3


B-737
OCH3
CHF2
—CH2-(2-Cl—C6H4)
—(CH2)3—CH3


B-738
CH3
CF3
—CH2-(2-Cl—C6H4)
—(CH2)3—CH3


B-739
CH2F
CF3
—CH2-(2-Cl—C6H4)
—(CH2)3—CH3


B-740
OCH3
CF3
—CH2-(2-Cl—C6H4)
—(CH2)3—CH3


B-741
CH3
CH3
—CH2-(3-Cl—C6H4)
—(CH2)3—CH3


B-742
CH2F
CH3
—CH2-(3-Cl—C6H4)
—(CH2)3—CH3


B-743
OCH3
CH3
—CH2-(3-Cl—C6H4)
—(CH2)3—CH3


B-744
CH3
CH2F
—CH2-(3-Cl—C6H4)
—(CH2)3—CH3


B-745
CH2F
CH2F
—CH2-(3-Cl—C6H4)
—(CH2)3—CH3


B-746
OCH3
CH2F
—CH2-(3-Cl—C6H4)
—(CH2)3—CH3


B-747
CH3
CHF2
—CH2-(3-Cl—C6H4)
—(CH2)3—CH3


B-748
CH2F
CHF2
—CH2-(3-Cl—C6H4)
—(CH2)3—CH3


B-749
OCH3
CHF2
—CH2-(3-Cl—C6H4)
—(CH2)3—CH3


B-750
CH3
CF3
—CH2-(3-Cl—C6H4)
—(CH2)3—CH3


B-751
CH2F
CF3
—CH2-(3-Cl—C6H4)
—(CH2)3—CH3


B-752
OCH3
CF3
—CH2-(3-Cl—C6H4)
—(CH2)3—CH3


B-753
CH3
CH3
—CH2-(4-Cl—C6H4)
—(CH2)3—CH3


B-754
CH2F
CH3
—CH2-(4-Cl—C6H4)
—(CH2)3—CH3


B-755
OCH3
CH3
—CH2-(4-Cl—C6H4)
—(CH2)3—CH3


B-756
CH3
CH2F
—CH2-(4-Cl—C6H4)
—(CH2)3—CH3


B-757
CH2F
CH2F
—CH2-(4-Cl—C6H4)
—(CH2)3—CH3


B-758
OCH3
CH2F
—CH2-(4-Cl—C6H4)
—(CH2)3—CH3


B-759
CH3
CHF2
—CH2-(4-Cl—C6H4)
—(CH2)3—CH3


B-760
CH2F
CHF2
—CH2-(4-Cl—C6H4)
—(CH2)3—CH3


B-761
OCH3
CHF2
—CH2-(4-Cl—C6H4)
—(CH2)3—CH3


B-762
CH3
CF3
—CH2-(4-Cl—C6H4)
—(CH2)3—CH3


B-763
CH2F
CF3
—CH2-(4-Cl—C6H4)
—(CH2)3—CH3


B-764
OCH3
CF3
—CH2-(4-Cl—C6H4)
—(CH2)3—CH3


B-765
CH3
CH3
—CH2-(2,4-Cl2—C6H3)
—(CH2)3—CH3


B-766
CH2F
CH3
—CH2-(2,4-Cl2—C6H3)
—(CH2)3—CH3


B-767
OCH3
CH3
—CH2-(2,4-Cl2—C6H3)
—(CH2)3—CH3


B-768
CH3
CH2F
—CH2-(2,4-Cl2—C6H3)
—(CH2)3—CH3


B-769
CH2F
CH2F
—CH2-(2,4-Cl2—C6H3)
—(CH2)3—CH3


B-770
OCH3
CH2F
—CH2-(2,4-Cl2—C6H3)
—(CH2)3—CH3


B-771
CH3
CHF2
—CH2-(2,4-Cl2—C6H3)
—(CH2)3—CH3


B-772
CH2F
CHF2
—CH2-(2,4-Cl2—C6H3)
—(CH2)3—CH3


B-773
OCH3
CHF2
—CH2-(2,4-Cl2—C6H3)
—(CH2)3—CH3


B-774
CH3
CF3
—CH2-(2,4-Cl2—C6H3)
—(CH2)3—CH3


B-775
CH2F
CF3
—CH2-(2,4-Cl2—C6H3)
—(CH2)3—CH3


B-776
OCH3
CF3
—CH2-(2,4-Cl2—C6H3)
—(CH2)3—CH3


B-777
CH3
CH3
—CH2—CH2—C6H5
—(CH2)3—CH3


B-778
CH2F
CH3
—CH2—CH2—C6H5
—(CH2)3—CH3


B-779
OCH3
CH3
—CH2—CH2—C6H5
—(CH2)3—CH3


B-780
CH3
CH2F
—CH2—CH2—C6H5
—(CH2)3—CH3


B-781
CH2F
CH2F
—CH2—CH2—C6H5
—(CH2)3—CH3


B-782
OCH3
CH2F
—CH2—CH2—C6H5
—(CH2)3—CH3


B-783
CH3
CHF2
—CH2—CH2—C6H5
—(CH2)3—CH3


B-784
CH2F
CHF2
—CH2—CH2—C6H5
—(CH2)3—CH3


B-785
OCH3
CHF2
—CH2—CH2—C6H5
—(CH2)3—CH3


B-786
CH3
CF3
—CH2—CH2—C6H5
—(CH2)3—CH3


B-787
CH2F
CF3
—CH2—CH2—C6H5
—(CH2)3—CH3


B-788
OCH3
CF3
—CH2—CH2—C6H5
—(CH2)3—CH3


B-789
CH3
CH3
C6H5
—CH—CH(CH3)2


B-790
CH2F
CH3
C6H5
—CH—CH(CH3)2


B-791
OCH3
CH3
C6H5
—CH—CH(CH3)2


B-792
CH3
CH2F
C6H5
—CH—CH(CH3)2


B-793
CH2F
CH2F
C6H5
—CH—CH(CH3)2


B-794
OCH3
CH2F
C6H5
—CH—CH(CH3)2


B-795
CH3
CHF2
C6H5
—CH—CH(CH3)2


B-796
CH2F
CHF2
C6H5
—CH—CH(CH3)2


B-797
OCH3
CHF2
C6H5
—CH—CH(CH3)2


B-798
CH3
CF3
C6H5
—CH—CH(CH3)2


B-799
CH2F
CF3
C6H5
—CH—CH(CH3)2


B-800
OCH3
CF3
C6H5
—CH—CH(CH3)2


B-801
CH3
CH3
—CH2—C6H5
—CH—CH(CH3)2


B-802
CH2F
CH3
—CH2—C6H5
—CH—CH(CH3)2


B-803
OCH3
CH3
—CH2—C6H5
—CH—CH(CH3)2


B-804
CH3
CH2F
—CH2—C6H5
—CH—CH(CH3)2


B-805
CH2F
CH2F
—CH2—C6H5
—CH—CH(CH3)2


B-806
OCH3
CH2F
—CH2—C6H5
—CH—CH(CH3)2


B-807
CH3
CHF2
—CH2—C6H5
—CH—CH(CH3)2


B-808
CH2F
CHF2
—CH2—C6H5
—CH—CH(CH3)2


B-809
OCH3
CHF2
—CH2—C6H5
—CH—CH(CH3)2


B-810
CH3
CF3
—CH2—C6H5
—CH—CH(CH3)2


B-811
CH2F
CF3
—CH2—C6H5
—CH—CH(CH3)2


B-812
OCH3
CF3
—CH2—C6H5
—CH—CH(CH3)2


B-813
CH3
CH3
—CH2-(2-F—C6H4)
—CH—CH(CH3)2


B-814
CH2F
CH3
—CH2-(2-F—C6H4)
—CH—CH(CH3)2


B-815
OCH3
CH3
—CH2-(2-F—C6H4)
—CH—CH(CH3)2


B-816
CH3
CH2F
—CH2-(2-F—C6H4)
—CH—CH(CH3)2


B-817
CH2F
CH2F
—CH2-(2-F—C6H4)
—CH—CH(CH3)2


B-818
OCH3
CH2F
—CH2-(2-F—C6H4)
—CH—CH(CH3)2


B-819
CH3
CHF2
—CH2-(2-F—C6H4)
—CH—CH(CH3)2


B-820
CH2F
CHF2
—CH2-(2-F—C6H4)
—CH—CH(CH3)2


B-821
OCH3
CHF2
—CH2-(2-F—C6H4)
—CH—CH(CH3)2


B-822
CH3
CF3
—CH2-(2-F—C6H4)
—CH—CH(CH3)2


B-823
CH2F
CF3
—CH2-(2-F—C6H4)
—CH—CH(CH3)2


B-824
OCH3
CF3
—CH2-(2-F—C6H4)
—CH—CH(CH3)2


B-825
CH3
CH3
—CH2-(3-F—C6H4)
—CH—CH(CH3)2


B-826
CH2F
CH3
—CH2-(3-F—C6H4)
—CH—CH(CH3)2


B-827
OCH3
CH3
—CH2-(3-F—C6H4)
—CH—CH(CH3)2


B-828
CH3
CH2F
—CH2-(3-F—C6H4)
—CH—CH(CH3)2


B-829
CH2F
CH2F
—CH2-(3-F—C6H4)
—CH—CH(CH3)2


B-830
OCH3
CH2F
—CH2-(3-F—C6H4)
—CH—CH(CH3)2


B-831
CH3
CHF2
—CH2-(3-F—C6H4)
—CH—CH(CH3)2


B-832
CH2F
CHF2
—CH2-(3-F—C6H4)
—CH—CH(CH3)2


B-833
OCH3
CHF2
—CH2-(3-F—C6H4)
—CH—CH(CH3)2


B-834
CH3
CF3
—CH2-(3-F—C6H4)
—CH—CH(CH3)2


B-835
CH2F
CF3
—CH2-(3-F—C6H4)
—CH—CH(CH3)2


B-836
OCH3
CF3
—CH2-(3-F—C6H4)
—CH—CH(CH3)2


B-837
CH3
CH3
—CH2-(4-F—C6H4)
—CH—CH(CH3)2


B-838
CH2F
CH3
—CH2-(4-F—C6H4)
—CH—CH(CH3)2


B-839
OCH3
CH3
—CH2-(4-F—C6H4)
—CH—CH(CH3)2


B-840
CH3
CH2F
—CH2-(4-F—C6H4)
—CH—CH(CH3)2


B-841
CH2F
CH2F
—CH2-(4-F—C6H4)
—CH—CH(CH3)2


B-842
OCH3
CH2F
—CH2-(4-F—C6H4)
—CH—CH(CH3)2


B-843
CH3
CHF2
—CH2-(4-F—C6H4)
—CH—CH(CH3)2


B-844
CH2F
CHF2
—CH2-(4-F—C6H4)
—CH—CH(CH3)2


B-845
OCH3
CHF2
—CH2-(4-F—C6H4)
—CH—CH(CH3)2


B-846
CH3
CF3
—CH2-(4-F—C6H4)
—CH—CH(CH3)2


B-847
CH2F
CF3
—CH2-(4-F—C6H4)
—CH—CH(CH3)2


B-848
OCH3
CF3
—CH2-(4-F—C6H4)
—CH—CH(CH3)2


B-849
CH3
CH3
—CH2-(2,4-F2—C6H3)
—CH—CH(CH3)2


B-850
CH2F
CH3
—CH2-(2,4-F2—C6H3)
—CH—CH(CH3)2


B-851
OCH3
CH3
—CH2-(2,4-F2—C6H3)
—CH—CH(CH3)2


B-852
CH3
CH2F
—CH2-(2,4-F2—C6H3)
—CH—CH(CH3)2


B-853
CH2F
CH2F
—CH2-(2,4-F2—C6H3)
—CH—CH(CH3)2


B-854
OCH3
CH2F
—CH2-(2,4-F2—C6H3)
—CH—CH(CH3)2


B-855
CH3
CHF2
—CH2-(2,4-F2—C6H3)
—CH—CH(CH3)2


B-856
CH2F
CHF2
—CH2-(2,4-F2—C6H3)
—CH—CH(CH3)2


B-857
OCH3
CHF2
—CH2-(2,4-F2—C6H3)
—CH—CH(CH3)2


B-858
CH3
CF3
—CH2-(2,4-F2—C6H3)
—CH—CH(CH3)2


B-859
CH2F
CF3
—CH2-(2,4-F2—C6H3)
—CH—CH(CH3)2


B-860
OCH3
CF3
—CH2-(2,4-F2—C6H3)
—CH—CH(CH3)2


B-861
CH3
CH3
—CH2-(2-Cl—C6H4)
—CH—CH(CH3)2


B-862
CH2F
CH3
—CH2-(2-Cl—C6H4)
—CH—CH(CH3)2


B-863
OCH3
CH3
—CH2-(2-Cl—C6H4)
—CH—CH(CH3)2


B-864
CH3
CH2F
—CH2-(2-Cl—C6H4)
—CH—CH(CH3)2


B-865
CH2F
CH2F
—CH2-(2-Cl—C6H4)
—CH—CH(CH3)2


B-866
OCH3
CH2F
—CH2-(2-Cl—C6H4)
—CH—CH(CH3)2


B-867
CH3
CHF2
—CH2-(2-Cl—C6H4)
—CH—CH(CH3)2


B-868
CH2F
CHF2
—CH2-(2-Cl—C6H4)
—CH—CH(CH3)2


B-869
OCH3
CHF2
—CH2-(2-Cl—C6H4)
—CH—CH(CH3)2


B-870
CH3
CF3
—CH2-(2-Cl—C6H4)
—CH—CH(CH3)2


B-871
CH2F
CF3
—CH2-(2-Cl—C6H4)
—CH—CH(CH3)2


B-872
OCH3
CF3
—CH2-(2-Cl—C6H4)
—CH—CH(CH3)2


B-873
CH3
CH3
—CH2-(3-Cl—C6H4)
—CH—CH(CH3)2


B-874
CH2F
CH3
—CH2-(3-Cl—C6H4)
—CH—CH(CH3)2


B-875
OCH3
CH3
—CH2-(3-Cl—C6H4)
—CH—CH(CH3)2


B-876
CH3
CH2F
—CH2-(3-Cl—C6H4)
—CH—CH(CH3)2


B-877
CH2F
CH2F
—CH2-(3-Cl—C6H4)
—CH—CH(CH3)2


B-878
OCH3
CH2F
—CH2-(3-Cl—C6H4)
—CH—CH(CH3)2


B-879
CH3
CHF2
—CH2-(3-Cl—C6H4)
—CH—CH(CH3)2


B-880
CH2F
CHF2
—CH2-(3-Cl—C6H4)
—CH—CH(CH3)2


B-881
OCH3
CHF2
—CH2-(3-Cl—C6H4)
—CH—CH(CH3)2


B-882
CH3
CF3
—CH2-(3-Cl—C6H4)
—CH—CH(CH3)2


B-883
CH2F
CF3
—CH2-(3-Cl—C6H4)
—CH—CH(CH3)2


B-884
OCH3
CF3
—CH2-(3-Cl—C6H4)
—CH—CH(CH3)2


B-885
CH3
CH3
—CH2-(4-Cl—C6H4)
—CH—CH(CH3)2


B-886
CH2F
CH3
—CH2-(4-Cl—C6H4)
—CH—CH(CH3)2


B-887
OCH3
CH3
—CH2-(4-Cl—C6H4)
—CH—CH(CH3)2


B-888
CH3
CH2F
—CH2-(4-Cl—C6H4)
—CH—CH(CH3)2


B-889
CH2F
CH2F
—CH2-(4-Cl—C6H4)
—CH—CH(CH3)2


B-890
OCH3
CH2F
—CH2-(4-Cl—C6H4)
—CH—CH(CH3)2


B-891
CH3
CHF2
—CH2-(4-Cl—C6H4)
—CH—CH(CH3)2


B-892
CH2F
CHF2
—CH2-(4-Cl—C6H4)
—CH—CH(CH3)2


B-893
OCH3
CHF2
—CH2-(4-Cl—C6H4)
—CH—CH(CH3)2


B-894
CH3
CF3
—CH2-(4-Cl—C6H4)
—CH—CH(CH3)2


B-895
CH2F
CF3
—CH2-(4-Cl—C6H4)
—CH—CH(CH3)2


B-896
OCH3
CF3
—CH2-(4-Cl—C6H4)
—CH—CH(CH3)2


B-897
CH3
CH3
—CH2-(2,4-Cl2—C6H3)
—CH—CH(CH3)2


B-898
CH2F
CH3
—CH2-(2,4-Cl2—C6H3)
—CH—CH(CH3)2


B-899
OCH3
CH3
—CH2-(2,4-Cl2—C6H3)
—CH—CH(CH3)2


B-900
CH3
CH2F
—CH2-(2,4-Cl2—C6H3)
—CH—CH(CH3)2


B-901
CH2F
CH2F
—CH2-(2,4-Cl2—C6H3)
—CH—CH(CH3)2


B-902
OCH3
CH2F
—CH2-(2,4-Cl2—C6H3)
—CH—CH(CH3)2


B-903
CH3
CHF2
—CH2-(2,4-Cl2—C6H3)
—CH—CH(CH3)2


B-904
CH2F
CHF2
—CH2-(2,4-Cl2—C6H3)
—CH—CH(CH3)2


B-905
OCH3
CHF2
—CH2-(2,4-Cl2—C6H3)
—CH—CH(CH3)2


B-906
CH3
CF3
—CH2-(2,4-Cl2—C6H3)
—CH—CH(CH3)2


B-907
CH2F
CF3
—CH2-(2,4-Cl2—C6H3)
—CH—CH(CH3)2


B-908
OCH3
CF3
—CH2-(2,4-Cl2—C6H3)
—CH—CH(CH3)2


B-909
CH3
CH3
—CH2—CH2—C6H5
—CH—CH(CH3)2


B-910
CH2F
CH3
—CH2—CH2—C6H5
—CH—CH(CH3)2


B-911
OCH3
CH3
—CH2—CH2—C6H5
—CH—CH(CH3)2


B-912
CH3
CH2F
—CH2—CH2—C6H5
—CH—CH(CH3)2


B-913
CH2F
CH2F
—CH2—CH2—C6H5
—CH—CH(CH3)2


B-914
OCH3
CH2F
—CH2—CH2—C6H5
—CH—CH(CH3)2


B-915
CH3
CHF2
—CH2—CH2—C6H5
—CH—CH(CH3)2


B-916
CH2F
CHF2
—CH2—CH2—C6H5
—CH—CH(CH3)2


B-917
OCH3
CHF2
—CH2—CH2—C6H5
—CH—CH(CH3)2


B-918
CH3
CF3
—CH2—CH2—C6H5
—CH—CH(CH3)2


B-919
CH2F
CF3
—CH2—CH2—C6H5
—CH—CH(CH3)2


B-920
OCH3
CF3
—CH2—CH2—C6H5
—CH—CH(CH3)2


B-921
CH3
CH3
C6H5
—CH(CH3)—CH2—CH3


B-922
CH2F
CH3
C6H5
—CH(CH3)—CH2—CH3


B-923
OCH3
CH3
C6H5
—CH(CH3)—CH2—CH3


B-924
CH3
CH2F
C6H5
—CH(CH3)—CH2—CH3


B-925
CH2F
CH2F
C6H5
—CH(CH3)—CH2—CH3


B-926
OCH3
CH2F
C6H5
—CH(CH3)—CH2—CH3


B-927
CH3
CHF2
C6H5
—CH(CH3)—CH2—CH3


B-928
CH2F
CHF2
C6H5
—CH(CH3)—CH2—CH3


B-929
OCH3
CHF2
C6H5
—CH(CH3)—CH2—CH3


B-930
CH3
CF3
C6H5
—CH(CH3)—CH2—CH3


B-931
CH2F
CF3
C6H5
—CH(CH3)—CH2—CH3


B-932
OCH3
CF3
C6H5
—CH(CH3)—CH2—CH3


B-933
CH3
CH3
—CH2—C6H5
—CH(CH3)—CH2—CH3


B-934
CH2F
CH3
—CH2—C6H5
—CH(CH3)—CH2—CH3


B-935
OCH3
CH3
—CH2—C6H5
—CH(CH3)—CH2—CH3


B-936
CH3
CH2F
—CH2—C6H5
—CH(CH3)—CH2—CH3


B-937
CH2F
CH2F
—CH2—C6H5
—CH(CH3)—CH2—CH3


B-938
OCH3
CH2F
—CH2—C6H5
—CH(CH3)—CH2—CH3


B-939
CH3
CHF2
—CH2—C6H5
—CH(CH3)—CH2—CH3


B-940
CH2F
CHF2
—CH2—C6H5
—CH(CH3)—CH2—CH3


B-941
OCH3
CHF2
—CH2—C6H5
—CH(CH3)—CH2—CH3


B-942
CH3
CF3
—CH2—C6H5
—CH(CH3)—CH2—CH3


B-943
CH2F
CF3
—CH2—C6H5
—CH(CH3)—CH2—CH3


B-944
OCH3
CF3
—CH2—C6H5
—CH(CH3)—CH2—CH3


B-945
CH3
CH3
—CH2-(2-F—C6H4)
—CH(CH3)—CH2—CH3


B-946
CH2F
CH3
—CH2-(2-F—C6H4)
—CH(CH3)—CH2—CH3


B-947
OCH3
CH3
—CH2-(2-F—C6H4)
—CH(CH3)—CH2—CH3


B-948
CH3
CH2F
—CH2-(2-F—C6H4)
—CH(CH3)—CH2—CH3


B-949
CH2F
CH2F
—CH2-(2-F—C6H4)
—CH(CH3)—CH2—CH3


B-950
OCH3
CH2F
—CH2-(2-F—C6H4)
—CH(CH3)—CH2—CH3


B-951
CH3
CHF2
—CH2-(2-F—C6H4)
—CH(CH3)—CH2—CH3


B-952
CH2F
CHF2
—CH2-(2-F—C6H4)
—CH(CH3)—CH2—CH3


B-953
OCH3
CHF2
—CH2-(2-F—C6H4)
—CH(CH3)—CH2—CH3


B-954
CH3
CF3
—CH2-(2-F—C6H4)
—CH(CH3)—CH2—CH3


B-955
CH2F
CF3
—CH2-(2-F—C6H4)
—CH(CH3)—CH2—CH3


B-956
OCH3
CF3
—CH2-(2-F—C6H4)
—CH(CH3)—CH2—CH3


B-957
CH3
CH3
—CH2-(3-F—C6H4)
—CH(CH3)—CH2—CH3


B-958
CH2F
CH3
—CH2-(3-F—C6H4)
—CH(CH3)—CH2—CH3


B-959
OCH3
CH3
—CH2-(3-F—C6H4)
—CH(CH3)—CH2—CH3


B-960
CH3
CH2F
—CH2-(3-F—C6H4)
—CH(CH3)—CH2—CH3


B-961
CH2F
CH2F
—CH2-(3-F—C6H4)
—CH(CH3)—CH2—CH3


B-962
OCH3
CH2F
—CH2-(3-F—C6H4)
—CH(CH3)—CH2—CH3


B-963
CH3
CHF2
—CH2-(3-F—C6H4)
—CH(CH3)—CH2—CH3


B-964
CH2F
CHF2
—CH2-(3-F—C6H4)
—CH(CH3)—CH2—CH3


B-965
OCH3
CHF2
—CH2-(3-F—C6H4)
—CH(CH3)—CH2—CH3


B-966
CH3
CF3
—CH2-(3-F—C6H4)
—CH(CH3)—CH2—CH3


B-967
CH2F
CF3
—CH2-(3-F—C6H4)
—CH(CH3)—CH2—CH3


B-968
OCH3
CF3
—CH2-(3-F—C6H4)
—CH(CH3)—CH2—CH3


B-969
CH3
CH3
—CH2-(4-F—C6H4)
—CH(CH3)—CH2—CH3


B-970
CH2F
CH3
—CH2-(4-F—C6H4)
—CH(CH3)—CH2—CH3


B-971
OCH3
CH3
—CH2-(4-F—C6H4)
—CH(CH3)—CH2—CH3


B-972
CH3
CH2F
—CH2-(4-F—C6H4)
—CH(CH3)—CH2—CH3


B-973
CH2F
CH2F
—CH2-(4-F—C6H4)
—CH(CH3)—CH2—CH3


B-974
OCH3
CH2F
—CH2-(4-F—C6H4)
—CH(CH3)—CH2—CH3


B-975
CH3
CHF2
—CH2-(4-F—C6H4)
—CH(CH3)—CH2—CH3


B-976
CH2F
CHF2
—CH2-(4-F—C6H4)
—CH(CH3)—CH2—CH3


B-977
OCH3
CHF2
—CH2-(4-F—C6H4)
—CH(CH3)—CH2—CH3


B-978
CH3
CF3
—CH2-(4-F—C6H4)
—CH(CH3)—CH2—CH3


B-979
CH2F
CF3
—CH2-(4-F—C6H4)
—CH(CH3)—CH2—CH3


B-980
OCH3
CF3
—CH2-(4-F—C6H4)
—CH(CH3)—CH2—CH3


B-981
CH3
CH3
—CH2-(2,4-F2—C6H3)
—CH(CH3)—CH2—CH3


B-982
CH2F
CH3
—CH2-(2,4-F2—C6H3)
—CH(CH3)—CH2—CH3


B-983
OCH3
CH3
—CH2-(2,4-F2—C6H3)
—CH(CH3)—CH2—CH3


B-984
CH3
CH2F
—CH2-(2,4-F2—C6H3)
—CH(CH3)—CH2—CH3


B-985
CH2F
CH2F
—CH2-(2,4-F2—C6H3)
—CH(CH3)—CH2—CH3


B-986
OCH3
CH2F
—CH2-(2,4-F2—C6H3)
—CH(CH3)—CH2—CH3


B-987
CH3
CHF2
—CH2-(2,4-F2—C6H3)
—CH(CH3)—CH2—CH3


B-988
CH2F
CHF2
—CH2-(2,4-F2—C6H3)
—CH(CH3)—CH2—CH3


B-989
OCH3
CHF2
—CH2-(2,4-F2—C6H3)
—CH(CH3)—CH2—CH3


B-990
CH3
CF3
—CH2-(2,4-F2—C6H3)
—CH(CH3)—CH2—CH3


B-991
CH2F
CF3
—CH2-(2,4-F2—C6H3)
—CH(CH3)—CH2—CH3


B-992
OCH3
CF3
—CH2-(2,4-F2—C6H3)
—CH(CH3)—CH2—CH3


B-993
CH3
CH3
—CH2-(2-Cl—C6H4)
—CH(CH3)—CH2—CH3


B-994
CH2F
CH3
—CH2-(2-Cl—C6H4)
—CH(CH3)—CH2—CH3


B-995
OCH3
CH3
—CH2-(2-Cl—C6H4)
—CH(CH3)—CH2—CH3


B-996
CH3
CH2F
—CH2-(2-Cl—C6H4)
—CH(CH3)—CH2—CH3


B-997
CH2F
CH2F
—CH2-(2-Cl—C6H4)
—CH(CH3)—CH2—CH3


B-998
OCH3
CH2F
—CH2-(2-Cl—C6H4)
—CH(CH3)—CH2—CH3


B-999
CH3
CHF2
—CH2-(2-Cl—C6H4)
—CH(CH3)—CH2—CH3


B-1000
CH2F
CHF2
—CH2-(2-Cl—C6H4)
—CH(CH3)—CH2—CH3


B-1001
OCH3
CHF2
—CH2-(2-Cl—C6H4)
—CH(CH3)—CH2—CH3


B-1002
CH3
CF3
—CH2-(2-Cl—C6H4)
—CH(CH3)—CH2—CH3


B-1003
CH2F
CF3
—CH2-(2-Cl—C6H4)
—CH(CH3)—CH2—CH3


B-1004
OCH3
CF3
—CH2-(2-Cl—C6H4)
—CH(CH3)—CH2—CH3


B-1005
CH3
CH3
—CH2-(3-Cl—C6H4)
—CH(CH3)—CH2—CH3


B-1006
CH2F
CH3
—CH2-(3-Cl—C6H4)
—CH(CH3)—CH2—CH3


B-1007
OCH3
CH3
—CH2-(3-Cl—C6H4)
—CH(CH3)—CH2—CH3


B-1008
CH3
CH2F
—CH2-(3-Cl—C6H4)
—CH(CH3)—CH2—CH3


B-1009
CH2F
CH2F
—CH2-(3-Cl—C6H4)
—CH(CH3)—CH2—CH3


B-1010
OCH3
CH2F
—CH2-(3-Cl—C6H4)
—CH(CH3)—CH2—CH3


B-1011
CH3
CHF2
—CH2-(3-Cl—C6H4)
—CH(CH3)—CH2—CH3


B-1012
CH2F
CHF2
—CH2-(3-Cl—C6H4)
—CH(CH3)—CH2—CH3


B-1013
OCH3
CHF2
—CH2-(3-Cl—C6H4)
—CH(CH3)—CH2—CH3


B-1014
CH3
CF3
—CH2-(3-Cl—C6H4)
—CH(CH3)—CH2—CH3


B-1015
CH2F
CF3
—CH2-(3-Cl—C6H4)
—CH(CH3)—CH2—CH3


B-1016
OCH3
CF3
—CH2-(3-Cl—C6H4)
—CH(CH3)—CH2—CH3


B-1017
CH3
CH3
—CH2-(4-Cl—C6H4)
—CH(CH3)—CH2—CH3


B-1018
CH2F
CH3
—CH2-(4-Cl—C6H4)
—CH(CH3)—CH2—CH3


B-1019
OCH3
CH3
—CH2-(4-Cl—C6H4)
—CH(CH3)—CH2—CH3


B-1020
CH3
CH2F
—CH2-(4-Cl—C6H4)
—CH(CH3)—CH2—CH3


B-1021
CH2F
CH2F
—CH2-(4-Cl—C6H4)
—CH(CH3)—CH2—CH3


B-1022
OCH3
CH2F
—CH2-(4-Cl—C6H4)
—CH(CH3)—CH2—CH3


B-1023
CH3
CHF2
—CH2-(4-Cl—C6H4)
—CH(CH3)—CH2—CH3


B-1024
CH2F
CHF2
—CH2-(4-Cl—C6H4)
—CH(CH3)—CH2—CH3


B-1025
OCH3
CHF2
—CH2-(4-Cl—C6H4)
—CH(CH3)—CH2—CH3


B-1026
CH3
CF3
—CH2-(4-Cl—C6H4)
—CH(CH3)—CH2—CH3


B-1027
CH2F
CF3
—CH2-(4-Cl—C6H4)
—CH(CH3)—CH2—CH3


B-1028
OCH3
CF3
—CH2-(4-Cl—C6H4)
—CH(CH3)—CH2—CH3


B-1029
CH3
CH3
—CH2-(2,4-Cl2—C6H3)
—CH(CH3)—CH2—CH3


B-1030
CH2F
CH3
—CH2-(2,4-Cl2—C6H3)
—CH(CH3)—CH2—CH3


B-1031
OCH3
CH3
—CH2-(2,4-Cl2—C6H3)
—CH(CH3)—CH2—CH3


B-1032
CH3
CH2F
—CH2-(2,4-Cl2—C6H3)
—CH(CH3)—CH2—CH3


B-1033
CH2F
CH2F
—CH2-(2,4-Cl2—C6H3)
—CH(CH3)—CH2—CH3


B-1034
OCH3
CH2F
—CH2-(2,4-Cl2—C6H3)
—CH(CH3)—CH2—CH3


B-1035
CH3
CHF2
—CH2-(2,4-Cl2—C6H3)
—CH(CH3)—CH2—CH3


B-1036
CH2F
CHF2
—CH2-(2,4-Cl2—C6H3)
—CH(CH3)—CH2—CH3


B-1037
OCH3
CHF2
—CH2-(2,4-Cl2—C6H3)
—CH(CH3)—CH2—CH3


B-1038
CH3
CF3
—CH2-(2,4-Cl2—C6H3)
—CH(CH3)—CH2—CH3


B-1039
CH2F
CF3
—CH2-(2,4-Cl2—C6H3)
—CH(CH3)—CH2—CH3


B-1040
OCH3
CF3
—CH2-(2,4-Cl2—C6H3)
—CH(CH3)—CH2—CH3


B-1041
CH3
CH3
—CH2—CH2—C6H5
—CH(CH3)—CH2—CH3


B-1042
CH2F
CH3
—CH2—CH2—C6H5
—CH(CH3)—CH2—CH3


B-1043
OCH3
CH3
—CH2—CH2—C6H5
—CH(CH3)—CH2—CH3


B-1044
CH3
CH2F
—CH2—CH2—C6H5
—CH(CH3)—CH2—CH3


B-1045
CH2F
CH2F
—CH2—CH2—C6H5
—CH(CH3)—CH2—CH3


B-1046
OCH3
CH2F
—CH2—CH2—C6H5
—CH(CH3)—CH2—CH3


B-1047
CH3
CHF2
—CH2—CH2—C6H5
—CH(CH3)—CH2—CH3


B-1048
CH2F
CHF2
—CH2—CH2—C6H5
—CH(CH3)—CH2—CH3


B-1049
OCH3
CHF2
—CH2—CH2—C6H5
—CH(CH3)—CH2—CH3


B-1050
CH3
CF3
—CH2—CH2—C6H5
—CH(CH3)—CH2—CH3


B-1051
CH2F
CF3
—CH2—CH2—C6H5
—CH(CH3)—CH2—CH3


B-1052
OCH3
CF3
—CH2—CH2—C6H5
—CH(CH3)—CH2—CH3


B-1053
CH3
CH3
C6H5
—C(CH3)3


B-1054
CH2F
CH3
C6H5
—C(CH3)3


B-1055
OCH3
CH3
C6H5
—C(CH3)3


B-1056
CH3
CH2F
C6H5
—C(CH3)3


B-1057
CH2F
CH2F
C6H5
—C(CH3)3


B-1058
OCH3
CH2F
C6H5
—C(CH3)3


B-1059
CH3
CHF2
C6H5
—C(CH3)3


B-1060
CH2F
CHF2
C6H5
—C(CH3)3


B-1061
OCH3
CHF2
C6H5
—C(CH3)3


B-1062
CH3
CF3
C6H5
—C(CH3)3


B-1063
CH2F
CF3
C6H5
—C(CH3)3


B-1064
OCH3
CF3
C6H5
—C(CH3)3


B-1065
CH3
CH3
—CH2—C6H5
—C(CH3)3


B-1066
CH2F
CH3
—CH2—C6H5
—C(CH3)3


B-1067
OCH3
CH3
—CH2—C6H5
—C(CH3)3


B-1068
CH3
CH2F
—CH2—C6H5
—C(CH3)3


B-1069
CH2F
CH2F
—CH2—C6H5
—C(CH3)3


B-1070
OCH3
CH2F
—CH2—C6H5
—C(CH3)3


B-1071
CH3
CHF2
—CH2—C6H5
—C(CH3)3


B-1072
CH2F
CHF2
—CH2—C6H5
—C(CH3)3


B-1073
OCH3
CHF2
—CH2—C6H5
—C(CH3)3


B-1074
CH3
CF3
—CH2—C6H5
—C(CH3)3


B-1075
CH2F
CF3
—CH2—C6H5
—C(CH3)3


B-1076
OCH3
CF3
—CH2—C6H5
—C(CH3)3


B-1077
CH3
CH3
—CH2-(2-F—C6H4)
—C(CH3)3


B-1078
CH2F
CH3
—CH2-(2-F—C6H4)
—C(CH3)3


B-1079
OCH3
CH3
—CH2-(2-F—C6H4)
—C(CH3)3


B-1080
CH3
CH2F
—CH2-(2-F—C6H4)
—C(CH3)3


B-1081
CH2F
CH2F
—CH2-(2-F—C6H4)
—C(CH3)3


B-1082
OCH3
CH2F
—CH2-(2-F—C6H4)
—C(CH3)3


B-1083
CH3
CHF2
—CH2-(2-F—C6H4)
—C(CH3)3


B-1084
CH2F
CHF2
—CH2-(2-F—C6H4)
—C(CH3)3


B-1085
OCH3
CHF2
—CH2-(2-F—C6H4)
—C(CH3)3


B-1086
CH3
CF3
—CH2-(2-F—C6H4)
—C(CH3)3


B-1087
CH2F
CF3
—CH2-(2-F—C6H4)
—C(CH3)3


B-1088
OCH3
CF3
—CH2-(2-F—C6H4)
—C(CH3)3


B-1089
CH3
CH3
—CH2-(3-F—C6H4)
—C(CH3)3


B-1090
CH2F
CH3
—CH2-(3-F—C6H4)
—C(CH3)3


B-1091
OCH3
CH3
—CH2-(3-F—C6H4)
—C(CH3)3


B-1092
CH3
CH2F
—CH2-(3-F—C6H4)
—C(CH3)3


B-1093
CH2F
CH2F
—CH2-(3-F—C6H4)
—C(CH3)3


B-1094
OCH3
CH2F
—CH2-(3-F—C6H4)
—C(CH3)3


B-1095
CH3
CHF2
—CH2-(3-F—C6H4)
—C(CH3)3


B-1096
CH2F
CHF2
—CH2-(3-F—C6H4)
—C(CH3)3


B-1097
OCH3
CHF2
—CH2-(3-F—C6H4)
—C(CH3)3


B-1098
CH3
CF3
—CH2-(3-F—C6H4)
—C(CH3)3


B-1099
CH2F
CF3
—CH2-(3-F—C6H4)
—C(CH3)3


B-1100
OCH3
CF3
—CH2-(3-F—C6H4)
—C(CH3)3


B-1101
CH3
CH3
—CH2-(4-F—C6H4)
—C(CH3)3


B-1102
CH2F
CH3
—CH2-(4-F—C6H4)
—C(CH3)3


B-1103
OCH3
CH3
—CH2-(4-F—C6H4)
—C(CH3)3


B-1104
CH3
CH2F
—CH2-(4-F—C6H4)
—C(CH3)3


B-1105
CH2F
CH2F
—CH2-(4-F—C6H4)
—C(CH3)3


B-1106
OCH3
CH2F
—CH2-(4-F—C6H4)
—C(CH3)3


B-1107
CH3
CHF2
—CH2-(4-F—C6H4)
—C(CH3)3


B-1108
CH2F
CHF2
—CH2-(4-F—C6H4)
—C(CH3)3


B-1109
OCH3
CHF2
—CH2-(4-F—C6H4)
—C(CH3)3


B-1110
CH3
CF3
—CH2-(4-F—C6H4)
—C(CH3)3


B-1111
CH2F
CF3
—CH2-(4-F—C6H4)
—C(CH3)3


B-1112
OCH3
CF3
—CH2-(4-F—C6H4)
—C(CH3)3


B-1113
CH3
CH3
—CH2-(2,4-F2—C6H3)
—C(CH3)3


B-1114
CH2F
CH3
—CH2-(2,4-F2—C6H3)
—C(CH3)3


B-1115
OCH3
CH3
—CH2-(2,4-F2—C6H3)
—C(CH3)3


B-1116
CH3
CH2F
—CH2-(2,4-F2—C6H3)
—C(CH3)3


B-1117
CH2F
CH2F
—CH2-(2,4-F2—C6H3)
—C(CH3)3


B-1118
OCH3
CH2F
—CH2-(2,4-F2—C6H3)
—C(CH3)3


B-1119
CH3
CHF2
—CH2-(2,4-F2—C6H3)
—C(CH3)3


B-1120
CH2F
CHF2
—CH2-(2,4-F2—C6H3)
—C(CH3)3


B-1121
OCH3
CHF2
—CH2-(2,4-F2—C6H3)
—C(CH3)3


B-1122
CH3
CF3
—CH2-(2,4-F2—C6H3)
—C(CH3)3


B-1123
CH2F
CF3
—CH2-(2,4-F2—C6H3)
—C(CH3)3


B-1124
OCH3
CF3
—CH2-(2,4-F2—C6H3)
—C(CH3)3


B-1125
CH3
CH3
—CH2-(2-Cl—C6H4)
—C(CH3)3


B-1126
CH2F
CH3
—CH2-(2-Cl—C6H4)
—C(CH3)3


B-1127
OCH3
CH3
—CH2-(2-Cl—C6H4)
—C(CH3)3


B-1128
CH3
CH2F
—CH2-(2-Cl—C6H4)
—C(CH3)3


B-1129
CH2F
CH2F
—CH2-(2-Cl—C6H4)
—C(CH3)3


B-1130
OCH3
CH2F
—CH2-(2-Cl—C6H4)
—C(CH3)3


B-1131
CH3
CHF2
—CH2-(2-Cl—C6H4)
—C(CH3)3


B-1132
CH2F
CHF2
—CH2-(2-Cl—C6H4)
—C(CH3)3


B-1133
OCH3
CHF2
—CH2-(2-Cl—C6H4)
—C(CH3)3


B-1134
CH3
CF3
—CH2-(2-Cl—C6H4)
—C(CH3)3


B-1135
CH2F
CF3
—CH2-(2-Cl—C6H4)
—C(CH3)3


B-1136
OCH3
CF3
—CH2-(2-Cl—C6H4)
—C(CH3)3


B-1137
CH3
CH3
—CH2-(3-Cl—C6H4)
—C(CH3)3


B-1138
CH2F
CH3
—CH2-(3-Cl—C6H4)
—C(CH3)3


B-1139
OCH3
CH3
—CH2-(3-Cl—C6H4)
—C(CH3)3


B-1140
CH3
CH2F
—CH2-(3-Cl—C6H4)
—C(CH3)3


B-1141
CH2F
CH2F
—CH2-(3-Cl—C6H4)
—C(CH3)3


B-1142
OCH3
CH2F
—CH2-(3-Cl—C6H4)
—C(CH3)3


B-1143
CH3
CHF2
—CH2-(3-Cl—C6H4)
—C(CH3)3


B-1144
CH2F
CHF2
—CH2-(3-Cl—C6H4)
—C(CH3)3


B-1145
OCH3
CHF2
—CH2-(3-Cl—C6H4)
—C(CH3)3


B-1146
CH3
CF3
—CH2-(3-Cl—C6H4)
—C(CH3)3


B-1147
CH2F
CF3
—CH2-(3-Cl—C6H4)
—C(CH3)3


B-1148
OCH3
CF3
—CH2-(3-Cl—C6H4)
—C(CH3)3


B-1149
CH3
CH3
—CH2-(4-Cl—C6H4)
—C(CH3)3


B-1150
CH2F
CH3
—CH2-(4-Cl—C6H4)
—C(CH3)3


B-1151
OCH3
CH3
—CH2-(4-Cl—C6H4)
—C(CH3)3


B-1152
CH3
CH2F
—CH2-(4-Cl—C6H4)
—C(CH3)3


B-1153
CH2F
CH2F
—CH2-(4-Cl—C6H4)
—C(CH3)3


B-1154
OCH3
CH2F
—CH2-(4-Cl—C6H4)
—C(CH3)3


B-1155
CH3
CHF2
—CH2-(4-Cl—C6H4)
—C(CH3)3


B-1156
CH2F
CHF2
—CH2-(4-Cl—C6H4)
—C(CH3)3


B-1157
OCH3
CHF2
—CH2-(4-Cl—C6H4)
—C(CH3)3


B-1158
CH3
CF3
—CH2-(4-Cl—C6H4)
—C(CH3)3


B-1159
CH2F
CF3
—CH2-(4-Cl—C6H4)
—C(CH3)3


B-1160
OCH3
CF3
—CH2-(4-Cl—C6H4)
—C(CH3)3


B-1161
CH3
CH3
—CH2-(2,4-Cl2—C6H3)
—C(CH3)3


B-1162
CH2F
CH3
—CH2-(2,4-Cl2—C6H3)
—C(CH3)3


B-1163
OCH3
CH3
—CH2-(2,4-Cl2—C6H3)
—C(CH3)3


B-1164
CH3
CH2F
—CH2-(2,4-Cl2—C6H3)
—C(CH3)3


B-1165
CH2F
CH2F
—CH2-(2,4-Cl2—C6H3)
—C(CH3)3


B-1166
OCH3
CH2F
—CH2-(2,4-Cl2—C6H3)
—C(CH3)3


B-1167
CH3
CHF2
—CH2-(2,4-Cl2—C6H3)
—C(CH3)3


B-1168
CH2F
CHF2
—CH2-(2,4-Cl2—C6H3)
—C(CH3)3


B-1169
OCH3
CHF2
—CH2-(2,4-Cl2—C6H3)
—C(CH3)3


B-1170
CH3
CF3
—CH2-(2,4-Cl2—C6H3)
—C(CH3)3


B-1171
CH2F
CF3
—CH2-(2,4-Cl2—C6H3)
—C(CH3)3


B-1172
OCH3
CF3
—CH2-(2,4-Cl2—C6H3)
—C(CH3)3


B-1173
CH3
CH3
—CH2—CH2—C6H5
—C(CH3)3


B-1174
CH2F
CH3
—CH2—CH2—C6H5
—C(CH3)3


B-1175
OCH3
CH3
—CH2—CH2—C6H5
—C(CH3)3


B-1176
CH3
CH2F
—CH2—CH2—C6H6
—C(CH3)3


B-1177
CH2F
CH2F
—CH2—CH2—C6H6
—C(CH3)3


B-1178
OCH3
CH2F
—CH2—CH2—C6H5
—C(CH3)3


B-1179
CH3
CHF2
—CH2—CH2—C6H6
—C(CH3)3


B-1180
CH2F
CHF2
—CH2—CH2—C6H5
—C(CH3)3


B-1181
OCH3
CHF2
—CH2—CH2—C6H5
—C(CH3)3


B-1182
CH3
CF3
—CH2—CH2—C6H5
—C(CH3)3


B-1183
CH2F
CF3
—CH2—CH2—C6H5
—C(CH3)3


B-1184
OCH3
CF3
—CH2—CH2—C6H5
—C(CH3)3









Table 1a Compounds of the formula I.A-1, I.A-2, I.A-3, I.A-4, I.B-1, I.B-2, I.B-3, I.B-4 and I.C-1, I.C-2, I.C-3, I.C-4 in which R6 is H and the meaning for the combination of R2, R3, R7 and R8 for each individual compound corresponds in each case to one line of Table B (compounds I.A-1.1a.B-1 to I.A-1.1a.B-1184, I.A-2.1a.B-1 to I.A-2.1a.B-1184, I.A-3.1a.B-1 to I.A-3.1a.B-1184, I.A-4.1a.B-1 to I.A-4.1a.B-1184; I.B-1.1a.B-1 to 1.6-1.1a.B-1184, I.B-2.1a.B-1 to 1.6-2.1a.B-1184, I.B-3.1a.B-1 to 1.6-3.1a.B-1184, I.B-4.1a.B-1 to 1.6-4.1a.B-1184; I.C-1.1a.B-1 to I.C-1.1a.B-1184, I.C-2.1a.B-1 to I.C-2.1a.B-1184, I.C-3.1a.B-1 to I.C-3.1a.B-1184, I.C-4.1a.B-1 to I.C-4.1a.B-1184).


Table 2a Compounds of the formula I.A-1, I.A-2, I.A-3, I.A-4, I.B-1, I.B-2, I.B-3, I.B-4 and I.C-1, I.C-2, I.C-3, I.C-4 in which R6 is CH3 and the meaning for the combination of R2, R3, R7 and R8 for each individual compound corresponds in each case to one line of Table B (compounds I.A-1.1b.B-1 to I.A-1.1b.B-1184, I.A-2.1b.B-1 to I.A-2.1b.B-1184, I.A-3.1b.B-1 to I.A-3.1b.B-1184, I.A-4.1b.B-1 to I.A-4.1b.B-1184;I.B-1.1b.B-1 to 1.6-1.1b.B-1184, I.B-2.1b.B-1 to 1.6-2.1b.B-1184, I.B-3.1b.B-1 to I.B-3.1b.B-1184, I.B-4.1b.B-1 to I.B-4.1b.B-1184; I.C-1.1b.B-1 to I.C-1.1b.B-1184, I.C-2.1b.B-1 to I.C-2.1b.B-1184, I.C-3.1b.B-1 to I.C-3.1b.B-1184, I.C-4.1b.B-1 to I.C-4.1b.B-1184).


Table 3a Compounds of the formula I.A-1, I.A-2, I.A-3, I.A-4, I.B-1, I.B-2, I.B-3, I.B-4 and I.C-1, I.C-2, I.C-3, I.C-4 in which R6 is —CH2—CH3 and the meaning for the combination of R2, R3, R7 and R8 for each individual compound corresponds in each case to one line of Table B (compounds I.A-1.1b.B-1 to I.A-1.1b.B-1184, I.A-2.1b.B-1 to I.A-2.1b.B-1184, I.A-3.1b.B-1 to I.A-3.1b.B-1184, I.A-4.1b.B-1 to I.A-4.1b.B-1184; I.B-1.1b.B-1 to I.B-1.1b.B-1184, I.B-2.1b.B-1 to I.B-2.1b.B-1184, I.B-3.1b.B-1 to I.B-3.1b.B-1184, I.B-4.1b.B-1 to I.B-4.1b.B-1184; I.C-1.1b.B-1 to I.C-1.1b.B-1184, I.C-2.1b.B-1 to I.C-2.1b.B-1184, I.C-3.1b.B-1 to I.C-3.1b.B-1184, I.C-4.1b.B-1 to I.C-4.1b.B-1184).


The compounds I and the compositions according to the invention, respectively, are suitable as fungicides. They are distinguished by an outstanding effectiveness against a broad spectrum of phytopathogenic fungi, including soil-borne fungi, which derive especially from the classes of the Plasmodiophoromycetes, Peronosporomycetes (syn. Oomycetes), Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, and Deuteromycetes (syn. Fungi imperfecti). Some are systemically effective and they can be used in crop protection as foliar fungicides, fungicides for seed dressing, and soil fungicides. Moreover, they are suitable for controlling harmful fungi, which inter alia occur in wood or roots of plants.


The compounds I and the compositions according to the invention are particularly important in the control of a multitude of phytopathogenic fungi on various cultivated plants, such as cereals, e. g. wheat, rye, barley, triticale, oats, or rice; beet, e. g. sugar beet or fodder beet; fruits, e. g. pomes (apples, pears, etc.), stone fruits (plums, peaches, almonds, cherries, etc.), or soft fruits, which are also called berries (strawberries, raspberries, blackberries, gooseberries, etc.); leguminous plants, e. g. lentils, peas, alfalfa, or soybeans; oil plants, e. g. rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts, or soybeans; cucurbits, e. g. squashes, cucumber, or melons; fiber plants, e. g. cotton, flax, hemp, or jute; citrus fruits, e. g. oranges, lemons, grapefruits, or mandarins; vegetables, e. g. spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, cucurbits, or paprika; lauraceous plants, e. g. avocados, cinnamon, or camphor; energy and raw material plants, e. g. corn, soybean, rape, sugar cane, or oil palm; corn; tobacco; nuts; coffee; tea; bananas; vines (table grapes and grape juice grape vines); hop; turf; sweet leaf (also called Stevia); natural rubber plants; or ornamental and forestry plants, e. g. flowers, shrubs, broad-leaved trees, or evergreens (conifers, eucalyptus, etc.); and on the plant propagation material, such as seeds; and on the crop material of these plants.


Preferably, compounds I and compositions thereof, respectively are used for controlling a multitude of fungi on field crops, such as potatoes, sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rape, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.


The term “plant propagation material” is to be understood to denote all the generative parts of the plant, such as seeds; and vegetative plant materials, such as cuttings and tubers (e. g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants; including seedlings and young plants, which are to be transplanted after germination or after emergence from soil. These young plants may also be protected before transplantation by a total or partial treatment by immersion or pouring.


Preferably, treatment of plant propagation materials with compounds I and compositions thereof, respectively, is used for controlling a multitude of fungi on cereals, such as wheat, rye, barley and oats; rice, corn, cotton and soybeans.


The term “cultivated plants” is to be understood as including plants which have been modified by mutagenesis or genetic engineering to provide a new trait to a plant or to modify an already present trait. Mutagenesis includes techniques of random mutagenesis using X-rays or mutagenic chemicals, but also techniques of targeted mutagenesis, to create mutations at a specific locus of a plant genome. Targeted mutagenesis techniques frequently use oligonucleotides or proteins like CRISPR/Cas, zinc-finger nucleases, TALENs or meganucleases to achieve the targeting effect. Genetic engineering usually uses recombinant DNA techniques to create modifications in a plant genome which under natural circumstances cannot readily be obtained by cross breeding, mutagenesis or natural recombination. Typically, one or more genes are integrated into the genome of a plant to add a trait or improve a trait. These integrated genes are also referred to as transgenes in the art, while plant comprising such transgenes are referred to as transgenic plants. The process of plant transformation usually produces several transformation events, which differ in the genomic locus in which a transgene has been integrated. Plants comprising a specific transgene on a specific genomic locus are usually described as comprising a specific “event”, which is referred to by a specific event name. Traits which have been introduced in plants or have been modified include herbicide tolerance, insect resistance, increased yield and tolerance to abiotic conditions, like drought.


Herbicide tolerance has been created by using mutagenesis as well as using genetic engineering. Plants which have been rendered tolerant to acetolactate synthase (ALS) inhibitor herbicides by mutagenesis and breeding comprise plant varieties commercially available under the name Clearfield®.


Herbicide tolerance has been created via the use of transgenes to glyphosate, glufosinate, 2,4-D, dicamba, oxynil herbicides, like bromoxynil and ioxynil, sulfonylurea herbicides, ALS inhibitors and 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, like isoxaflutole and mesotrione.


Transgenes which have been used to provide herbicide tolerance traits comprise: for tolerance to glyphosate: cp4 epsps, epsps grg23ace5, mepsps, 2mepsps, gat4601, gat4621, goxv247; for tolerance to glufosinate: pat and bar, for tolerance to 2,4-D: aad-1, aad-12; for tolerance to dicamba: dmo; for tolerance to oxynil herbicies: bxn; for tolerance to sulfonylurea herbicides: zm-hra, csr1-2, gm-hra, S4-HrA; for tolerance to ALS inhibitors: csr1-2; and for tolerance to HPPD inhibitors: hppdPF, W336, avhppd-03.


Transgenic corn events comprising herbicide tolerance genes include, but are not limited to, DAS40278, MON801, MON802, MON809, MON810, MON832, MON87411, MON87419, MON87427, MON88017, MON89034, NK603, GA21, MZHGOJG, HCEM485, VCO-01981-5, 676, 678, 680, 33121, 4114, 59122, 98140, Bt10, Bt176, CBH-351, DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507 and TC6275. Transgenic soybean events comprising herbicide tolerance genes include, but are not limited to, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21, A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS-81419-2, GU262, SYHTOH2, W62, W98, FG72 and CV127. Transgenic cotton events comprising herbicide tolerance genes include, but are not limited to, 19-51a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN10211, BXN10215, BXN10222, BXN10224, MON1445, MON1698, MON88701, MON88913, GHB119, GHB614, LLCotton25, T303-3 and T304-40. Transgenic canola events comprising herbicide tolerance genes are for example, but not excluding others, MON88302, HCR-1, HCN10, HCN28, HCN92, MS1, MS8, PHY14, PHY23, PHY35, PHY36, RF1, RF2 and RF3.


Insect resistance has mainly been created by transferring bacterial genes for insecticidal proteins to plants: Transgenes which have most frequently been used are toxin genes of Bacillus spp. and synthetic variants thereof, like cry1A, cry1Ab, cry1Ab-Ac, cry1Ac, cry1A.105, cry1F, cry1Fa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bb1, cry34Ab1, cry35Ab1, cry9C, vip3A(a), vip3Aa20. However, also genes of plant origin, such as genes coding for protease inhibitors, like CpTI and pinII, have been transferred to other plants. A further approach uses transgenes such as dvsnf7 to produce double-stranded RNA in plants.


Transgenic corn events comprising genes for insecticidal proteins or double stranded RNA include, but are not limited to, Bt10, Bt11, Bt176, MON801, MON802, MON809, MON810, MON863, MON87411, MON88017, MON89034, 33121, 4114, 5307, 59122, TC1507, TC6275, CBH-351, MIR162, DBT418 and MZIR098. Transgenic soybean events comprising genes for insecticidal proteins include, but are not limited to, MON87701, MON87751 and DAS-81419. Transgenic cotton events comprising genes for insecticidal proteins include, but are not limited to, SGK321, MON531, MON757, MON1076, MON15985, 31707, 31803, 31807, 31808, 42317, BNLA-601, Event1, COT67B, COT102, T303-3, T304-40, GFM Cry1A, GK12, MLS 9124, 281-24-236, 3006-210-23, GHB119 and SGK321.


Increased yield has been created by using the transgene athb17, being present for example in corn event MON87403, or by using the transgene bbx32, being present for example in the soybean event MON87712.


Cultivated plants comprising a modified oil content have been created by using the transgenes: gm-fad2-1, Pj.D6D, Nc.Fad3, fad2-1A and fatb1-A. Soybean events comprising at least one of these genes are: 260-05, MON87705 and MON87769.


Tolerance to abiotic conditions, such as drought, has been created by using the transgene cspB, comprised by the corn event MON87460 and by using the transgene Hahb-4, comprised by soybean event IND-00410-5.


Traits are frequently combined by combining genes in a transformation event or by combining different events during the breeding process resulting in a cultivated plant with stacked traits. Preferred combinations of traits are combinations of herbicide tolerance traits to different groups of herbicides, combinations of insect tolerance to different kind of insects, in particular tolerance to lepidopteran and coleopteran insects, combinations of herbicide tolerance with one or several types of insect resistance, combinations of herbicide tolerance with increased yield as well as combinations of herbicide tolerance and tolerance to abiotic conditions.


Plants comprising singular or stacked traits as well as the genes and events providing these traits are well known in the art. For example, detailed information as to the mutagenized or integrated genes and the respective events are available from websites of the organizations “International Service for the Acquisition of Agri-biotech Applications (ISAAA)” (http://www.isaaa.org/gmapprovaldatabase) and the “Center for Environmental Risk Assessment (CERA)” (http://cera-gmc.org/GMCropDatabase). Further information on specific events and methods to detect them can be found for canola events MS1, MS8, RF3, GT73, MON88302, KK179 in WO01/031042, WO01/041558, WO01/041558, WO02/036831, WO11/153186, WO13/003558, for cotton events MON1445, MON15985, MON531 (MON15985), LLCotton25, MON88913, COT102, 281-24-236, 3006-210-23, COT67B, GHB614, T304-40, GHB119, MON88701, 81910 in WO02/034946, WO02/100163, WO02/100163, WO03/013224, WO04/072235, WO04/039986, WO05/103266, WO05/103266, WO06/128573, WO07/017186, WO08/122406, WO08/151780, WO12/134808, WO13/112527; for corn events GA21, MON810, DLL25, TC1507, MON863, MIR604, LY038, MON88017, 3272, 59122, NK603, MIR162, MON89034, 98140, 32138, MON87460, 5307, 4114, MON87427, DAS40278, MON87411, 33121, MON87403, MON87419 in WO98/044140, U.S. Ser. No. 02/102,582, U.S. Ser. No. 03/126,634, WO04/099447, WO04/011601, WO05/103301, WO05/061720, WO05/059103, WO06/098952, WO06/039376, US2007/292854, WO07/142840, WO07/140256, WO08/112019, WO09/103049, WO09/111263, WO10/077816, WO11/084621, WO11/062904, WO11/022469, WO13/169923, WO14/116854, WO15/053998, WO15/142571; for potato events E12, F10, J3, J55, V11, X17, Y9 in WO14/178910, WO14/178913, WO14/178941, WO14/179276, WO16/183445, WO17/062831, WO17/062825; for rice events LLRICE06, LLRICE601, LLRICE62 in WO00/026345, WO00/026356, WO00/026345; and for soybean events H7-1, MON89788, A2704-12, A5547-127, DP305423, DP356043, MON87701, MON87769, CV127, MON87705, DAS68416-4, MON87708, MON87712, SYHTOH2, DAS81419, DAS81419×DAS44406-6, MON87751 in WO04/074492, WO06/130436, WO06/108674, WO06/108675, WO08/054747, WO08/002872, WO09/064652, WO09/102873, WO10/080829, WO10/037016, WO11/066384, WO11/034704, WO12/051199, WO12/082548, WO13/016527, WO13/016516, WO14/201235.


The use of compounds I and compositions according to the invention, respectively, on cultivated plants may result in effects which are specific to a cultivated plant comprising a certain gene or event. These effects might involve changes in growth behavior or changed resistance to biotic or abiotic stress factors. Such effects may in particular comprise enhanced yield, enhanced resistance or tolerance to insects, nematodes, fungal, bacterial, mycoplasma, viral or viroid pathogens as well as early vigour, early or delayed ripening, cold or heat tolerance as well as changed amino acid or fatty acid spectrum or content.


The compounds I and compositions thereof, respectively, are particularly suitable for controlling the following plant diseases:



Albugo spp. (white rust) on ornamentals, vegetables (e. g. A. candida) and sunflowers (e. g. A. tragopogonis); Alternaria spp. (Alternaria leaf spot) on vegetables, rape (A. brassicola or brassicae), sugar beets (A. tenuis), fruits, rice, soybeans, potatoes (e. g. A. solani or A. alternata), tomatoes (e. g. A. solani or A. alternata) and wheat; Aphanomyces spp. on sugar beets and vegetables; Ascochyta spp. on cereals and vegetables, e. g. A. tritici (anthracnose) on wheat and A. hordei on barley; Bipolaris and Drechslera spp. (teleomorph: Cochliobolus spp.), e. g. Southern leaf blight (D. maydis) or Northern leaf blight (B. zeicola) on corn, e. g. spot blotch (B. sorokiniana) on cereals and e. g. B. oryzae on rice and turfs; Blumeria (formerly Erysphe) graminis (powdery mildew) on cereals (e. g. on wheat or barley); Botrytis cinerea (teleomorph: Botryotinia fuckeliana: grey mold) on fruits and berries (e. g. strawberries), vegetables (e. g. lettuce, carrots, celery and cabbages), rape, flowers, vines, forestry plants and wheat; Bremia lactucae (downy mildew) on lettuce; Ceratocystis (syn. Ophiostoma) spp. (rot or wilt) on broad-leaved trees and evergreens, e. g. C. ulmi (Dutch elm disease) on elms; Cercospora spp. (Cercospora leaf spots) on corn (e. g. Gray leaf spot: C. zeae-maydis), rice, sugar beets (e. g. C. beticola), sugarcane, vegetables, coffee, soybeans (e. g. C. sojina or C. kikuchii) and rice; Cladosporium spp. on tomatoes (e. g. C. fulvum: leaf mold) and cereals, e. g. C. herbarum (black ear) on wheat; Claviceps purpurea (ergot) on cereals; Cochliobolus (anamorph: Helminthosporium of Bipolaris) spp. (leaf spots) on corn (C. carbonum), cereals (e. g. C. sativus, anamorph: B. sorokiniana) and rice (e. g. C. miyabeanus, anamorph: H. oryzae); Colletotrichum (teleomorph: Glomerella) spp. (anthracnose) on cotton (e. g. C. gossypi), corn (e. g. C. graminicola: Anthracnose stalk rot), soft fruits, potatoes (e. g. C. coccodes: black dot), beans (e. g. C. lindemuthianum) and soybeans (e. g. C. truncatum or C. gloeosporioides); Corticium spp., e. g. C. sasakii (sheath blight) on rice; Corynespora cassiicola (leaf spots) on soybeans and ornamentals; Cycloconium spp., e. g. C. oleaginum on olive trees; Cylindrocarpon spp. (e. g. fruit tree canker or young vine decline, teleomorph: Nectria or Neonectria spp.) on fruit trees, vines (e. g. C. liriodendri, teleomorph: Neonectria liriodendri Black Foot Disease) and ornamentals; Dematophora (teleomorph: Rosellinia) necatrx (root and stem rot) on soybeans; Diaporthe spp., e. g. D. phaseolorum (damping off) on soybeans; Drechslera (syn. Helminthosporium, teleomorph: Pyrenophora) spp. on corn, cereals, such as barley (e. g. D. teres, net blotch) and wheat (e. g. D. tritici-repentis: tan spot), rice and turf; Esca (dieback, apoplexy) on vines, caused by Formitiporia (syn. Phellinus) punctata, F. mediterranea, Phaeomoniella chlamydospora (earlier Phaeoacremonium chlamydosporum), Phaeoacremonium aleophilum and/or Botryosphaeria obtusa; Elsinoe spp. on pome fruits (E. pyri), soft fruits (E. veneta: anthracnose) and vines (E. ampelina: anthracnose); Entyloma oryzae (leaf smut) on rice; Epicoccum spp. (black mold) on wheat; Erysiohe spp. (powdery mildew) on sugar beets (E. betae), vegetables (e. g. E. pisi), such as cucurbits (e. g. E. cichoracearum), cabbages, rape (e. g. E. cruciferarum); Eutypa lata (Eutypa canker or dieback, anamorph: Cytosporina lata, syn. Libertella blepharis) on fruit trees, vines and ornamental woods; Exserohilum (syn. Helminthosporium) spp. on corn (e. g. E. turcicum); Fusarium (teleomorph: Gibberella) spp. (wilt, root or stem rot) on various plants, such as F. graminearum or F. culmorum (root rot, scab or head blight) on cereals (e. g. wheat or barley), F. oxysporum on tomatoes, F. solani (f. sp. glycines now syn. F. virguliforme) and F. tucumaniae and F. braslilense each causing sudden death syndrome on soybeans, and F. verticillioides on corn; Gaeumannomyces graminis (take-all) on cereals (e. g. wheat or barley) and corn; Gibberella spp. on cereals (e. g. G. zeae) and rice (e. g. G. fujikuroi: Bakanae disease); Glomerella cingulata on vines, pome fruits and other plants and G. gossypi on cotton; Grainstaining complex on rice; Guignardia bidwellii (black rot) on vines; Gymnosporangium spp. on rosaceous plants and junipers, e. g. G. sabinae (rust) on pears; Helminthosporium spp. (syn. Drechslera, teleomorph: Cochliobolus) on corn, cereals and rice; Hemleia spp., e. g. H. vastatrix (coffee leaf rust) on coffee; Isariopsis clavispora (syn. Cladosporium vitis) on vines; Macrophomina phaseolina (syn. phaseoli) (root and stem rot) on soybeans and cotton; Microdochium (syn. Fusarium) nivale (pink snow mold) on cereals (e. g. wheat or barley); Microsphaera diffusa (powdery mildew) on soybeans; Monilinia spp., e. g. M. laxa, M. fructicola and M. fructigena (bloom and twig blight, brown rot) on stone fruits and other rosaceous plants; Mycosphaerella spp. on cereals, bananas, soft fruits and ground nuts, such as e. g. M. graminicola (anamorph: Septoria tritici, Septoria blotch) on wheat or M. fliensis (black Sigatoka disease) on bananas; Peronospora spp. (downy mildew) on cabbage (e. g. P. brassicae), rape (e. g. P. parasitica), onions (e. g. P. destructor), tobacco (P. tabacina) and soybeans (e. g. P. manshurica); Phakopsora pachyrhlzi and P. meibomiae (soybean rust) on soybeans; Phialophora spp. e. g. on vines (e. g. P. trachephila and P. tetraspora) and soybeans (e. g. P. gregata: stem rot); Phoma lingam (root and stem rot) on rape and cabbage and P. betae (root rot, leaf spot and damping-off) on sugar beets; Phomopsis spp. on sunflowers, vines (e. g. P. viticola: can and leaf spot) and soybeans (e. g. stem rot: P. phaseol, teleomorph: Diaporthe phaseolorum); Physoderma maydis (brown spots) on corn; Phytophthora spp. (wilt, root, leaf, fruit and stem root) on various plants, such as paprika and cucurbits (e. g. P. capsic), soybeans (e. g. P. megasperma, syn. P. sojae), potatoes and tomatoes (e. g. P. infestans: late blight) and broad-leaved trees (e. g. P. ramorum: sudden oak death); Plasmodiophora brassicae (club root) on cabbage, rape, radish and other plants; Plasmopara spp., e. g. P. viticola (grapevine downy mildew) on vines and P. halstedii on sunflowers; Podosphaera spp. (powdery mildew) on rosaceous plants, hop, pome and soft fruits, e. g. P. leucotricha on apples; Polymyxa spp., e. g. on cereals, such as barley and wheat (P. graminis) and sugar beets (P. betae) and thereby transmitted viral diseases; Pseudocercosporella herpotrichoides (eyespot, teleomorph: Tapesia yallundae) on cereals, e. g. wheat or barley; Pseudoperonospora (downy mildew) on various plants, e. g. P. cubensis on cucurbits or P. humili on hop; Pseudopezicula trachephila (red fire disease or ‘rotbrenner’, anamorph: Phialophora) on vines; Puccinia spp. (rusts) on various plants, e. g. P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. hordei (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust) on cereals, such as e. g. wheat, barley or rye, P. kuehnii (orange rust) on sugar cane and P. asparagi on asparagus; Pyrenophora (anamorph: Drechslera) tritici-repentis (tan spot) on wheat or P. teres (net blotch) on barley; Pyricularia spp., e. g. P. oryzae (teleomorph: Magnaporthe grisea, rice blast) on rice and P. grisea on turf and cereals; Pythium spp. (damping-off) on turf, rice, corn, wheat, cotton, rape, sunflowers, soybeans, sugar beets, vegetables and various other plants (e. g. P. ultimum or P. aphanidermatum); Ramularia spp., e. g. R. collo-cygni (Ramularia leaf spots, Physiological leaf spots) on barley and R. beticola on sugar beets; Rhizoctonia spp. on cotton, rice, potatoes, turf, corn, rape, potatoes, sugar beets, vegetables and various other plants, e. g. R. solani (root and stem rot) on soybeans, R. solani (sheath blight) on rice or R. cerealis (Rhizoctonia spring blight) on wheat or barley; Rhizopus stolonifer (black mold, soft rot) on strawberries, carrots, cabbage, vines and tomatoes; Rhynchosporium secals (scald) on barley, rye and triticale; Sarocladium oryzae and S. attenuatum (sheath rot) on rice; Sclerotinia spp. (stem rot or white mold) on vegetables and field crops, such as rape, sunflowers (e. g. S. sclerotiorum) and soybeans (e. g. S. rolfsii or S. sclerotiorum); Septoria spp. on various plants, e. g. S. glycines (brown spot) on soybeans, S. tritici (Septoria blotch) on wheat and S. (syn. Stagonospora) nodorum (Stagonospora blotch) on cereals; Uncinula (syn. Erysphe) necator (powdery mildew, anamorph: Oidium tuckeri) on vines; Setospaeria Spp. (Leaf Blight) on Corn (e. g. S. turcicum, Syn. Helminthosporium turcicum) and turf; Sphacelotheca spp. (smut) on corn, (e. g. S. reliana: head smut), sorghum und sugar cane; Sphaerotheca fuliginea (powdery mildew) on cucurbits; Spongospora subterranea (powdery scab) on potatoes and thereby transmitted viral diseases; Stagonospora spp. on cereals, e. g. S. nodorum (Stagonospora blotch, teleomorph: Leptosphaeria [syn. Phaeosphaeria] nodorum) on wheat; Synchytrium endobioticum on potatoes (potato wart disease); Taphrina spp., e. g. T. deformans (leaf curl disease) on peaches and T. pruni (plum pocket) on plums; Thielaviopsis spp. (black root rot) on tobacco, pome fruits, vegetables, soybeans and cotton, e. g. T. basicola (syn. Chalara elegans); Tietia spp. (common bunt or stinking smut) on cereals, such as e. g. T. tritici (syn. T caries, wheat bunt) and T. controversa (dwarf bunt) on wheat; Typhula incarnata (grey snow mold) on barley or wheat; Urocystis spp., e. g. U. occulta (stem smut) on rye; Uromyces spp. (rust) on vegetables, such as beans (e. g. U. appendiculatus, syn. U. phaseoli) and sugar beets (e. g. U. betae); Ustilago spp. (loose smut) on cereals (e. g. U. nuda and U. avaenae), corn (e. g. U. maydis: corn smut) and sugar cane; Venturia spp. (scab) on apples (e. g. V. inaequais) and pears; and Verticillium spp. (wilt) on various plants, such as fruits and ornamentals, vines, soft fruits, vegetables and field crops, e. g. V. dahliae on strawberries, rape, potatoes and tomatoes.


The compounds I and compositions thereof, respectively, are also suitable for controlling harmful microorganisms in the protection of stored products or harvest, and in the protection of materials.


The term “stored products or harvest” is understood to denote natural substances of plant or animal origin and their processed forms, which have been taken from the natural life cycle and for which long-term protection is desired. Stored products of crop plant origin, such as plants or parts thereof, for example stalks, leafs, tubers, seeds, fruits or grains, can be protected in the freshly harvested state or in processed form, such as pre-dried, moistened, comminuted, ground, pressed or roasted, which process is also known as post-harvest treatment. Also falling under the definition of stored products is timber, whether in the form of crude timber, such as construction timber, electricity pylons and barriers, or in the form of finished articles, such as furniture or objects made from wood. Stored products of animal origin are hides, leather, furs, hairs and the like. Preferably, “stored products” is understood to denote natural substances of plant origin and their processed forms, more preferably fruits and their processed forms, such as pomes, stone fruits, soft fruits and citrus fruits and their processed forms. The compounds I and compositions thereof according the present invention can prevent disadvantageous effects such as decay, discoloration or mold.


The term “protection of materials” is to be understood to denote the protection of technical and non-living materials, such as adhesives, glues, wood, paper, paperboard, textiles, leather, paint dispersions, plastics, cooling lubricants, fiber, or fabrics; against the infestation and destruction by harmful microorganisms, such as fungi and bacteria. As to the protection of materials, particular attention is paid to the following harmful fungi: Ascomycetes, such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp.; Basidiomycetes, such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Poria spp., Serpula spp. and Tyromyces spp.; Deuteromycetes, such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Alternaria spp., Paecilomyces spp.; and Zygomycetes, such as Mucor spp.


In the protection of stored products and harvest in addition the following yeast fungi are worthy of note: Candida spp. and Saccharomyces cerevisae.


The compounds I and compositions thereof, respectively, may be used for improving the health of a plant. The invention also relates to a method for improving plant health by treating a plant, its propagation material, and/or the locus where the plant is growing or is to grow with an effective amount of compounds I and compositions thereof, respectively.


The term “plant health” is to be understood to denote a condition of the plant and/or its products which is determined by several indicators alone or in combination with each other, such as yield (e. g. increased biomass and/or increased content of valuable ingredients), plant vigor (e. g. improved plant growth and/or greener leaves (“greening effect”)), quality (e. g. improved content or composition of certain ingredients), and tolerance to abiotic and/or biotic stress. The above identified indicators for the health condition of a plant may be interdependent or may result from each other.


The compounds of formula I can be present in different crystal modifications whose biological activity may differ. They are likewise subject matter of the present invention.


The compounds I are employed as such or in form of compositions by treating the fungi, the plants, plant propagation materials, such as seeds; soil, surfaces, materials, or rooms to be protected from fungal attack with a fungicidally effective amount of the active substances. The application can be carried out both before and after the infection of the plants, plant propagation materials, such as seeds; soil, surfaces, materials or rooms by the fungi.


Plant propagation materials may be treated with compounds I as such or a composition comprising at least one compound I prophylactically either at or before planting or transplanting.


The invention also relates to agrochemical compositions comprising an auxiliary and at least one compound I according to the invention.


An agrochemical composition comprises a fungicidally effective amount of a compound I.


The term “fungicidally effective amount” denotes an amount of the composition or of the compounds I, which is sufficient for controlling harmful fungi on cultivated plants or in the protection of stored products or harvest or of materials and which does not result in a substantial damage to the treated plants, the treated stored products or harvest, or to the treated materials. Such an amount can vary in a broad range and is dependent on various factors, such as the fungal species to be controlled, the treated cultivated plant, stored product, harvest or material, the climatic conditions and the specific compound I used.


The compounds I, their N-oxides and salts can be converted into customary types of agrochemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for composition types are suspensions (e. g. SC, OD, FS), emulsifiable concentrates (e. g. EC), emulsions (e. g. EW, EO, ES, ME), capsules (e. g. CS, ZC), pastes, pastilles, wettable powders or dusts (e. g. WP, SP, WS, DP, DS), pressings (e. g. BR, TB, DT), granules (e. g. WG, SG, GR, FG, GG, MG), insecticidal articles (e. g. LN), as well as gel formulations for the treatment of plant propagation materials, such as seeds (e. g. GF). These and further compositions types are defined in the “Catalogue of pesticide formulation types and international coding system”, Technical Monograph No. 2, 6th Ed. May 2008, CropLife International.


The compositions are prepared in a known manner, such as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or by Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.


Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers, and binders.


Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e. g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin, tetrahydronaphthalene, and alkylated naphthalenes; alcohols, e. g. ethanol, propanol, butanol, benzyl alcohol, cyclohexanol, glycols; DMSO; ketones, e. g. cyclohexanone; esters, e. g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e. g. methyl pyrrolidone, fatty acid dimethyl amides; and mixtures thereof.


Suitable solid carriers or fillers are mineral earths, e. g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, e. g. cellulose, starch; fertilizers, e. g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e. g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.


Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol. 1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).


Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylaryl sulfonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and of alkyl naphthalenes, sulfosuccinates, or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids, of oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.


Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide. Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters, or monoglycerides. Examples of sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters, or alkylpolyglucosides. Examples of polymeric surfactants are home- or copolymers of vinyl pyrrolidone, vinyl alcohols, or vinyl acetate.


Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetains and imidazolines. Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide, and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinyl amines or polyethylene amines.


Suitable adjuvants are compounds, which have a negligible or even no pesticidal activity themselves, and which improve the biological performance of the compound I on the target. Examples are surfactants, mineral or vegetable oils, and other auxiliaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.


Suitable thickeners are polysaccharides (e. g. xanthan gum, carboxymethyl cellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates.


Suitable bactericides are bronopol and isothiazolinone derivatives, such as alkylisothiazolinones and benzisothiazolinones.


Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.


Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.


Suitable colorants (e. g. in red, blue, or green) are pigments of low water solubility and water-soluble dyes. Examples are inorganic colorants (e. g. iron oxide, titan oxide, iron hexacyanoferrate) and organic colorants (e. g. alizarin-, azo- and phthalocyanine colorants).


Suitable tackifiers or binders are polyvinyl pyrrolidones, polyvinyl acetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.


Examples for composition types and their preparation are:


i) Water-Soluble Concentrates (SL, LS)


10-60 wt % of a compound I and 5-15 wt % wetting agent (e. g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e. g. alcohols) ad 100 wt %. The active substance dissolves upon dilution with water.


ii) Dispersible Concentrates (DC)


5-25 wt % of a compound I and 1-10 wt % dispersant (e. g. polyvinyl pyrrolidone) are dissolved in organic solvent (e. g. cyclohexanone) ad 100 wt %. Dilution with water gives a dispersion.


iii) Emulsifiable Concentrates (EC)


15-70 wt % of a compound I and 5-10 wt % emulsifiers (e. g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in water-insoluble organic solvent (e. g. aromatic hydrocarbon) ad 100 wt %. Dilution with water gives an emulsion.


iv) Emulsions (EW, EO, ES)


5-40 wt % of a compound I and 1-10 wt % emulsifiers (e. g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt % water-insoluble organic solvent (e. g. aromatic hydrocarbon). This mixture is introduced into water ad 100 wt % by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion.


v) Suspensions (SC, OD, FS)


In an agitated ball mill, 20-60 wt % of a compound I are comminuted with addition of 2-10 wt % dispersants and wetting agents (e. g. sodium lignosulfonate and alcohol ethoxylate), 0.1-2 wt % thickener (e. g. xanthan gum) and water ad 100 wt % to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. For FS type composition, up to 40 wt % binder (e. g. polyvinyl alcohol) is added.


vi) Water-Dispersible Granules and Water-Soluble Granules (WG, SG)


50-80 wt % of a compound I are ground finely with addition of dispersants and wetting agents (e. g. sodium lignosulfonate and alcohol ethoxylate) ad 100 wt % and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.


vii) Water-Dispersible Powders and Water-Soluble Powders (WP, SP, WS)


50-80 wt % of a compound I are ground in a rotor-stator mill with addition of 1-5 wt % dispersants (e. g. sodium lignosulfonate), 1-3 wt % wetting agents (e. g. alcohol ethoxylate) and solid carrier (e. g. silica gel) ad 100 wt %. Dilution with water gives a stable dispersion or solution of the active substance.


viii) Gel (GW, GF)


In an agitated ball mill, 5-25 wt % of a compound I are comminuted with addition of 3-10 wt % dispersants (e. g. sodium lignosulfonate), 1-5 wt % thickener (e. g. carboxymethyl cellulose) and water ad 100 wt % to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.


ix) Microemulsion (ME)


5-20 wt % of a compound I are added to 5-30 wt % organic solvent blend (e. g. fatty acid dimethyl amide and cyclohexanone), 10-25 wt % surfactant blend (e. g. alcohol ethoxylate and arylphenol ethoxylate), and water ad 100%. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion.


x) Microcapsules (CS)


An oil phase comprising 5-50 wt % of a compound I, 0-40 wt % water insoluble organic solvent (e. g. aromatic hydrocarbon), 2-15 wt % acrylic monomers (e. g. methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e. g. polyvinyl alcohol). Radical polymerization results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5-50 wt % of a compound I according to the invention, 0-40 wt % water insoluble organic solvent (e. g. aromatic hydrocarbon), and an isocyanate monomer (e. g. diphenylmethene-4,4′-diisocyanate) are dispersed into an aqueous solution of a protective colloid (e. g. polyvinyl alcohol). The addition of a polyamine (e. g. hexamethylenediamine) results in the formation of polyurea microcapsules. The monomers amount to 1-10 wt %. The wt % relate to the total CS composition.


xi) Dustable Powders (DP, DS)


1-10 wt % of a compound I are ground finely and mixed intimately with solid carrier (e. g. finely divided kaolin) ad 100 wt %.


xii) Granules (GR, FG)


0.5-30 wt % of a compound I is ground finely and associated with solid carrier (e. g. silicate) ad 100 wt %. Granulation is achieved by extrusion, spray-drying or fluidized bed.


xiii) Ultra-Low Volume Liquids (UL)


1-50 wt % of a compound I are dissolved in organic solvent (e. g. aromatic hydrocarbon) ad 100 wt %.


The compositions types i) to xiii) may optionally comprise further auxiliaries, such as 0.1-1 wt % bactericides, 5-15 wt % anti-freezing agents, 0.1-1 wt % anti-foaming agents, and 0.1-1 wt % colorants.


The agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, more preferably between 1 and 70%, and in particular between 10 and 60%, by weight of active substance. The active substances are employed in a purity of from 90% to 100%, preferably from 95-% to 100% (according to NMR spectrum).


For the purposes of treatment of plant propagation materials, particularly seeds, solutions for seed treatment (LS), Suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC), and gels (GF) are usually employed. The compositions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40%, in the ready-to-use preparations. Application can be carried out before or during sowing. Methods for applying compound I and compositions thereof, respectively, onto plant propagation material, especially seeds, include dressing, coating, pelleting, dusting, soaking, as well as in-furrow application methods. Preferably, compound I or the compositions thereof, respectively, are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating, and dusting.


When employed in plant protection, the amounts of active substances applied are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha, and in particular from 0.1 to 0.75 kg per ha.


In treatment of plant propagation materials, such as seeds, e. g. by dusting, coating, or drenching, amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kg of plant propagation material (preferably seeds) are generally required.


When used in the protection of materials or stored products, the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.


Various types of oils, wetters, adjuvants, fertilizer, or micronutrients, and further pesticides (e. g. herbicides, insecticides, fungicides, growth regulators, safeners, biopesticides) may be added to the active substances or the compositions comprising them as premix, or, if appropriate, not until immediately prior to use (tank mix). These agents can be admixed with the compositions according to the invention in a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.


A pesticide is generally a chemical or biological agent (such as pestidal active ingredient, compound, composition, virus, bacterium, antimicrobial, or disinfectant) that through its effect deters, incapacitates, kills or otherwise discourages pests. Target pests can include insects, plant pathogens, weeds, mollusks, birds, mammals, fish, nematodes (roundworms), and microbes that destroy property, cause nuisance, spread disease or are vectors for disease. The term “pesticide” includes also plant growth regulators that alter the expected growth, flowering, or reproduction rate of plants; defoliants that cause leaves or other foliage to drop from a plant, usually to facilitate harvest; desiccants that promote drying of living tissues, such as unwanted plant tops; plant activators that activate plant physiology for defense of against certain pests; safeners that reduce unwanted herbicidal action of pesticides on crop plants; and plant growth promoters that affect plant physiology e.g. to increase plant growth, biomass, yield or any other quality parameter of the harvestable goods of a crop plant.


Biopesticides have been defined as a form of pesticides based on microorganisms (bacteria, fungi, viruses, nematodes, etc.) or natural products (compounds, such as metabolites, proteins, or extracts from biological or other natural sources) (U.S. Environmental Protection Agency: http://www.epa.gov/pesticides/biopesticides/). Biopesticides fall into two major classes, microbial and biochemical pesticides:

    • (1) Microbial pesticides consist of bacteria, fungi or viruses (and often include the metabolites that bacteria and fungi produce). Entomopathogenic nematodes are also classified as microbial pesticides, even though they are multi-cellular.
    • (2) Biochemical pesticides are naturally occurring substances that control pests or provide other crop protection uses as defined below, but are relatively non-toxic to mammals.


The user applies the composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained. Usually, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.


According to one embodiment, individual components of the composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank or any other kind of vessel used for applications (e. g. seed treater drums, seed pelleting machinery, knapsack sprayer) and further auxiliaries may be added, if appropriate.


When living microorganisms, such as microbial pesticides from groups L1), L3) and L5), form part of such kit, it must be taken care that choice and amounts of the components (e. g. chemical pesticides) and of the further auxiliaries should not influence the viability of the microbial pesticides in the composition mixed by the user. Especially for bactericides and solvents, compatibility with the respective microbial pesticide has to be taken into account.


Consequently, one embodiment of the invention is a kit for preparing a usable pesticidal composition, the kit comprising a) a composition comprising component 1) as defined herein and at least one auxiliary; and b) a composition comprising component 2) as defined herein and at least one auxiliary; and optionally c) a composition comprising at least one auxiliary and optionally a further active component 3) as defined herein.


Mixing the compounds I or the compositions comprising them in the use form as fungicides with other fungicides results in many cases in an expansion of the fungicidal spectrum of activity being obtained or in a prevention of fungicide resistance development. Furthermore, in many cases, synergistic effects are obtained.


The following list of pesticides II (e. g. pesticidally-active substances and biopesticides), in conjunction with which the compounds I can be used, is intended to illustrate the possible combinations but does not limit them:


A) Respiration Inhibitors





    • Inhibitors of complex III at Qn site: azoxystrobin (A.1.1), coumethoxystrobin (A.1.2), coumoxystrobin (A.1.3), dimoxystrobin (A.1.4), enestroburin (A.1.5), fenaminstrobin (A.1.6), fenoxystrobin/flufenoxystrobin (A.1.7), fluoxastrobin (A.1.8), kresoxim-methyl (A.1.9), mandestrobin (A.1.10), metominostrobin (A.1.11), orysastrobin (A.1.12), picoxystrobin (A.1.13), pyraclostrobin (A.1.14), pyrametostrobin (A.1.15), pyraoxystrobin (A.1.16), trifloxystrobin (A.1.17), 2-(2-(3-(2,6-dichlorophenyl)-1-methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino-N-methyl-acetamide (A.1.18), pyribencarb (A.1.19), triclopyricarb/chlorodincarb (A.1.20), famoxadone (A.1.21), fenamidone (A.1.21), methyl-N-[2-[(1,4-dimethyl-5-phenyl-pyrazol-3-yl)oxylmethyl]phenyl]-N-methoxy-carbamate (A.1.22), metyltetrapole (A.1.25), (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]-oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (A.1.34), (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethylpent-3-enamide (A.1.35), pyriminostrobin (A.1.36), bifujunzhi (A.1.37), 2-(ortho-((2,5-dimethylphenyl-oxymethylen)phenyl)-3-methoxy-acrylic acid methylester (A.1.38);

    • inhibitors of complex III at Qi site: cyazofamid (A.2.1), amisulbrom (A.2.2), [(6S,7R,8R)-8-benzyl-3-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl] 2-methylpropanoate (A.2.3), fenpicoxamid (A.2.4), florylpicoxamid (A.2.5);

    • inhibitors of complex II: benodanil (A.3.1), benzovindiflupyr (A.3.2), bixafen (A.3.3), boscalid (A.3.4), carboxin (A.3.5), fenfuram (A.3.6), fluopyram (A.3.7), flutolanil (A.3.8), fluxapyroxad (A.3.9), furametpyr (A.3.10), isofetamid (A.3.11), isopyrazam (A.3.12), mepronil (A.3.13), oxycarboxin (A.3.14), penflufen (A.3.15), penthiopyrad (A.3.16), pydiflumetofen (A.3.17), pyraziflumid (A.3.18), sedaxane (A.3.19), tecloftalam (A.3.20), thifluzamide (A.3.21), inpyrfluxam (A.3.22), pyrapropoyne (A.3.23), fluindapyr (A.3.28), methyl (E)-2-[2-[(5-cyano-2-methyl-phenoxy)methyl]phenyl]-3-methoxy-prop-2-enoate (A.3.30), isoflucypram (A.3.31), 2-(difluoromethyl)-N-(1,1,3-trimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.32), 2-(difluoromethyl)-N-[(3R)-1,1,3-trimethylindan-4-yl]pyridine-3-carboxamide (A.3.33), 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.34), 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (A.3.35), 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide (A.3.36), 2-(difluoromethyl)-N-[(3R)-1,1-dimethyl-3-propyl-indan-4-yl]pyridine-3-carboxamide (A.3.37), 2-(difluoromethyl)-N-(3-isobutyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.38), 2-(difluoromethyl)-N-[(3R)-3-isobutyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (A.3.39);

    • other respiration inhibitors: diflumetorim (A.4.1); nitrophenyl derivates: binapacryl (A.4.2), dinobuton (A.4.3), dinocap (A.4.4), fluazinam (A.4.5), meptyldinocap (A.4.6), ferimzone (A.4.7); organometal compounds: fentin salts, e. g. fentin-acetate (A.4.8), fentin chloride (A.4.9) or fentin hydroxide (A.4.10); ametoctradin (A.4.11); silthiofam (A.4.12);





B) Sterol Biosynthesis Inhibitors (SBI Fungicides)





    • C14 demethylase inhibitors: triazoles: azaconazole (B.1.1), bitertanol (B.1.2), bromuconazole (B.1.3), cyproconazole (B.1.4), difenoconazole (B.1.5), diniconazole (B.1.6), diniconazole-M (B.1.7), epoxiconazole (B.1.8), fenbuconazole (B.1.9), fluquinconazole (B.1.10), flusilazole (B.1.11), flutriafol (B.1.12), hexaconazole (B.1.13), imibenconazole (B.1.14), ipconazole (B.1.15), metconazole (B.1.17), myclobutanil (B.1.18), oxpoconazole (B.1.19), paclobutrazole (B.1.20), penconazole (B.1.21), propiconazole (B.1.22), prothioconazole (B.1.23), simeconazole (B.1.24), tebuconazole (B.1.25), tetraconazole (B.1.26), triadimefon (B.1.27), triadimenol (B.1.28), triticonazole (B.1.29), uniconazole (B.1.30), 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(2,2,2-trifluoroethoxy)phenyl]-2-pyridyl]propan-2-ol (B.1.31), 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(trifluoromethoxy)phenyl]-2-pyridyl]propan-2-ol (B.1.32), ipfentrifluconazole (B.1.37), mefentrifluconazole (B.1.38), 2-(chloromethyl)-2-methyl-5-(p-tolylmethyl)-1-(1,2,4-triazol-1-ylmethyl)cyclopentanol (B.1.43); imidazoles: imazalil (B.1.44), pefurazoate (B.1.45), prochloraz (B.1.46), triflumizol (B.1.47); pyrimidines, pyridines, piperazines: fenarimol (B.1.49), pyrifenox (B.1.50), triforine (B.1.51), [3-(4-chloro-2-fluoro-phenyl)-5-(2,4-difluorophenyl)isoxazol-4-yl]-(3-pyridyl)methanol (B.1.52);

    • Delta14-reductase inhibitors: aldimorph (B.2.1), dodemorph (B.2.2), dodemorph-acetate (B.2.3), fenpropimorph (B.2.4), tridemorph (B.2.5), fenpropidin (B.2.6), piperalin (B.2.7), spiroxamine (B.2.8);

    • Inhibitors of 3-keto reductase: fenhexamid (B.3.1);

    • Other Sterol biosynthesis inhibitors: chlorphenomizole (B.4.1);





C) Nucleic Acid Synthesis Inhibitors





    • phenylamides or acyl amino acid fungicides: benalaxyl (C.1.1), benalaxyl-M (C.1.2), kiralaxyl (C.1.3), metalaxyl (C.1.4), metalaxyl-M (C.1.5), ofurace (C.1.6), oxadixyl (C.1.7);

    • other nucleic acid synthesis inhibitors: hymexazole (C.2.1), octhilinone (C.2.2), oxolinic acid (C.2.3), bupirimate (C.2.4), 5-fluorocytosine (C.2.5), 5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine (C.2.6), 5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4-amine (C.2.7), 5-fluoro-2-(4-chlorophenylmethoxy)pyrimidin-4 amine (C.2.8);





D) Inhibitors of Cell Division and Cytoskeleton





    • tubulin inhibitors: benomyl (D.1.1), carbendazim (D.1.2), fuberidazole (D1.3), thiabendazole (D.1.4),thiophanate-methyl(1.5), pyridachlometyl (D.1.6), (ethyl-2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]butanamide (D.1.8), ethyl-2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methylsulfanyl-acetamide (D.1.9), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)butanamide (D.1.10), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)-2-methoxy-acetamide (D.1.11), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-propyl-butanamide (D.1.12), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methoxy-N-propyl-acetamide (D.1.13), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methylsulfanyl-N-propyl-acetamide (D.1.14), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)-2-methylsulfanyl-acetamide (D.1.15), 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine (D.1.16);

    • other cell division inhibitors: diethofencarb (D.2.1), ethaboxam (D.2.2), pencycuron (D.2.3), fluopicolide (D.2.4), zoxamide (D.2.5), metrafenone (D.2.6), pyriofenone (D.2.7);





E) Inhibitors of Amino Acid and Protein Synthesis





    • methionine synthesis inhibitors: cyprodinil (E.1.1), mepanipyrim (E.1.2), pyrimethanil (E.1.3);

    • protein synthesis inhibitors: blasticidin-S (E.2.1), kasugamycin (E.2.2), kasugamycin hydrochloride-hydrate (E.2.3), mildiomycin (E.2.4), streptomycin (E.2.5), oxytetracyclin (E.2.6);





F) Signal Transduction Inhibitors





    • MAP/histidine kinase inhibitors: fluoroimid (F.1.1), iprodione (F.1.2), procymidone (F.1.3), vinclozolin (F.1.4), fludioxonil (F.1.5);

    • G protein inhibitors: quinoxyfen (F.2.1);





G) Lipid and Membrane Synthesis Inhibitors





    • Phospholipid biosynthesis inhibitors: edifenphos (G.1.1), iprobenfos (G.1.2), pyrazophos (G.1.3), isoprothiolane (G.1.4);

    • lipid peroxidation: dicloran (G.2.1), quintozene (G.2.2), tecnazene (G.2.3), tolclofos-methyl (G.2.4), biphenyl (G.2.5), chloroneb (G.2.6), etridiazole (G.2.7);

    • phospholipid biosynthesis and cell wall deposition: dimethomorph (G.3.1), flumorph (G.3.2), mandipropamid (G.3.3), pyrimorph (G.3.4), benthiavalicarb (G.3.5), iprovalicarb (G.3.6), valifenalate (G.3.7);

    • compounds affecting cell membrane permeability and fatty acides: propamocarb (G.4.1);

    • inhibitors of oxysterol binding protein: oxathiapiprolin (G.5.1), 2-{3-[2-(1-{[3,5-bis(difluoromethyl-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl methanesulfonate (G.5.2), 2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl) 1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate (G.5.3), 4-[1-[2-[3-(difluoromethyl)-5-methyl-pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-ylpyridine-2-carboxamide (G.5.4), 4-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.5), 4-[1-[2-[3-(difluoromethyl)-5-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.6), 4-[1-[2-[5-cyclopropyl-3-(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.7), 4-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-tetralin-1-yl-pyridine-2-carboxamide (G.5.8), 4-[1-[2-[5-(difluoromethyl)-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.9), 4-[1-[2-[3,5-bis(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.10), (4-[1-[2-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.11);


      H) Inhibitors with Multi Site Action

    • inorganic active substances: Bordeaux mixture (H.1.1), copper (H.1.2), copper acetate (H.1.3), copper hydroxide (H.1.4), copper oxychloride (H.1.5), basic copper sulfate (H.1.6), sulfur (H.1.7);

    • thio- and dithiocarbamates: ferbam (H.2.1), mancozeb (H.2.2), maneb (H.2.3), metam (H.2.4), metiram (H.2.5), propineb (H.2.6), thiram (H.2.7), zineb (H.2.8), ziram (H.2.9);

    • organochlorine compounds: anilazine (H.3.1), chlorothalonil (H.3.2), captafol (H.3.3), captan (H.3.4), folpet (H.3.5), dichlofluanid (H.3.6), dichlorophen (H.3.7), hexachlorobenzene (H.3.8), pentachlorphenole (H.3.9) and its salts, phthalide (H.3.10), tolylfluanid (H.3.11);

    • guanidines and others: guanidine (H.4.1), dodine (H.4.2), dodine free base (H.4.3), guazatine (H.4.4), guazatine-acetate (H.4.5), iminoctadine (H.4.6), iminoctadine-triacetate (H.4.7), iminoctadine-tris(albesilate) (H.4.8), dithianon (H.4.9), 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c′]dipyrrole-1,3,5,7(2H,6)-tetraone (H.4.10);





I) Cell Wall Synthesis Inhibitors





    • inhibitors of glucan synthesis: validamycin (1.1.1), polyoxin B (1.1.2);

    • melanin synthesis inhibitors: pyroquilon (1.2.1), tricyclazole (1.2.2), carpropamid (1.2.3), dicyclomet (1.2.4), fenoxanil (1.2.5);





J) Plant Defence Inducers





    • acibenzolar-S-methyl (J.1.1), probenazole (J.1.2), isotianil (J.1.3), tiadinil (J.1.4), prohexadione-calcium (J.1.5); phosphonates: fosetyl (J.1.6), fosetyl-aluminum (J.1.7), phosphorous acid and its salts (J.1.8), calcium phosphonate (J.1.11), potassium phosphonate (J.1.12), potassium or sodium bicarbonate (J.1.9), 4-cyclopropyl-N-(2,4-dimethoxyphenyl)thiadiazole-5-carboxamide (J.1.10);





K) Unknown Mode of Action





    • bronopol (K.1.1), chinomethionat (K.1.2), cyflufenamid (K.1.3), cymoxanil (K.1.4), dazomet (K.1.5), debacarb (K.1.6), diclocymet (K.1.7), diclomezine (K.1.8), difenzoquat (K.1.9), difenzoquat-methylsulfate (K.1.10), diphenylamin (K.1.11), fenitropan (K.1.12), fenpyrazamine (K.1.13), flumetover (K.1.14), flusulfamide (K.1.15), flutianil (K.1.16), harpin (K.1.17), methasulfocarb (K.1.18), nitrapyrin (K.1.19), nitrothal-isopropyl (K.1.20), tolprocarb (K.1.21), oxincopper (K.1.22), proquinazid (K.1.23), tebufloquin (K.1.24), tecloftalam (K.1.25), triazoxide (K.1.26), N′-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl formamidine (K.1.27), N′-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl formamidine (K.1.28), N′-[4-[[3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl]-oxy]-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine (K.1.29), N′-(5-bromo-6-indan-2-yloxy-2-methyl-3-pyridyl)-N-ethyl-N-methyl-formamidine (K.1.30), N′-[5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.31), N′-[5-bromo6-(4-isopropylcyclohexoxy)-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.32), N′-[5-bromo-2-methyl-6-(1-phenylethoxy)-3-pyridyl]-Methyl-N-methyl-formamidine (K.1.33), N′-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl formamidine (K.1.34), N′-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl formamidine (K.1.35), 2-(4-chloro-phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxy-acetamide (K.1.36), 3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine (pyrisoxazole) (K.1.37), 3-[5-(4-methylphenyl)-2,3-dimethyl-isoxazolidin-3 yl]-pyridine (K.1.38), 5-chloro-1-(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1H-benzoimidazole (K.1.39), ethyl (Z)-3-amino-2-cyano-3-phenyl-prop-2-enoate (K.1.40), picarbutrazox (K.1.41), pentyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate (K.1.42), but-3-ynyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate (K.1.43), ipflufenoquin (K.1.44), quinofumelin (K.1.47), 2-(6-benzyl-2-pyridyl)quinazoline (K.1.50), 2-[6-(3-fluoro-4-methoxy-phenyl)-5-methyl-2-pyridyl]quinazoline (K.1.51), dichlobentiazox (K.1.52), N′-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine (K.1.53), pyrifenamine (K.1.54);





L) Biopesticides





    • L1) Microbial pesticides with fungicidal, bactericidal, viricidal and/or plant defense activator activity: Ampelomyces quisqualis, Aspergillus flavus, Aureobasidium pullulans, Bacillus altitudinis, B. amyloliquefaciens, B. megaterium, B. mojavensis, B. mycoides, B. pumilus, B. simplex, B. solisalsi, B. subtilis, B. subtilis var. amyloliquefaciens, Candida oleophila, C. saitoana, Clavibacter michiganensis (bacteriophages), Coniothyrium minitans, Cryphonectria parasitica, Cryptococcus albidus, Dilophosphora alopecuri, Fusarium oxysporum, Clonostachys rosea f. catenulate (also named Gliocladium catenulatum), Gliocladium roseum, Lysobacter antibioticus, L. enzymogenes, Metschnikowia fructicola, Microdochium dimerum, Microsphaeropsis ochracea, Muscodor albus, Paenibacillus alvei, Paenibacillus epiphyticus, P. polymyxa, Pantoea vagans, Penicillium bilaiae, Phlebiopsis gigantea, Pseudomonas sp., Pseudomonas chloraphis, Pseudozyma flocculosa, Pichia anomala, Pythium oligandrum, Sphaerodes mycoparasitica, Streptomyces griseoviridis, S. lydicus, S. violaceusniger, Talaromyces flavus, Trichoderma asperelloides, T. asperellum, T. atroviride, T. fertile, T. gamsii, T. harmatum, T. harzianum, T. polysporum, T. stromaticum, T. virens, T. viride, Typhula phacorrhiza, Ulocladium oudemansii, Verticillium dahlia, zucchini yellow mosaic virus (avirulent strain);

    • L2) Biochemical pesticides with fungicidal, bactericidal, viricidal and/or plant defense activator activity: harpin protein, Reynoutria sachalinensis extract;

    • L3) Microbial pesticides with insecticidal, acaricidal, molluscidal and/or nematicidal activity: Agrobacterium radiobacter, Bacillus cereus, B. firmus, B. thuringiensis, B. thuringiensis ssp. aizawai, B. t. ssp. israelensis, B. t. ssp. galleriae, B. t. ssp. kurstaki, B. t. ssp. tenebrionis, Beauveria bassiana, B. brongniartii, Burkholderia spp., Chromobacterium subtsugae, Cydia pomonella granulovirus (CpGV), Cryptophlebia leucotreta granulovirus (CrleGV), Flavobacterium spp., Hellcoverpa armigera nucleopolyhedrovirus (HearNPV), Helicoverpazea nucleopolyhedrovirus (HzNPV), Helicoverpazea single capsid nucleopolyhedrovirus (HzSNPV), Heterorhabdtis bacteriophora, Isaria fumosorosea, Lecanicillium longisporum, L. muscarium, Metarhizium anisopliae, M. anisopliae var. anisopliae, M. anisopliae var. acridum, Nomuraea rileyi, Paecilomyces fumosoroseus, P. lilacinus, Paenibacillus popilliae, Pasteuria spp., P. nishizawae, P. penetrans, P. ramosa, P. thornea, P. usgae, Pseudomonas fluorescens, Spodoptera littoralis nucleopolyhedrovirus (SpliNPV), Steinernema carpocapsae, S. feltiae, S. kraussei, Streptomyces galbus, S. microflavus;

    • L4) Biochemical pesticides with insecticidal, acaricidal, molluscidal, pheromone and/or nematicidal activity: L-carvone, citral, (E,Z)-7,9-dodecadien-1-yl acetate, ethyl formate, (E,Z)-2,4-ethyl decadienoate (pear ester), (Z,Z,E)-7,11,13-hexadecatrienal, heptyl butyrate, isopropyl myristate, lavanulyl senecioate, cis-jasmone, 2-methyl 1-butanol, methyl eugenol, methyl jasmonate, (E,Z)-2,13-octadecadien-1-ol, (E,Z)-2,13-octadecadien-1-ol acetate, (E,Z)-3,13-octadecadien-1-ol, (R)-1-octen-3-ol, pentatermanone, (E,Z,Z)-3,8,11-tetradecatrienyl acetate, (Z,E)-9,12-tetradecadien-1-yl acetate, (Z)-7-tetradecen-2-one, (Z)-9-tetradecen-1-yl acetate, (Z)-11-tetradecenal, (Z)-11-tetradecen-1-ol, extract of Chenopodium ambrosiodes, Neem oil, Quillay extract;

    • L5) Microbial pesticides with plant stress reducing, plant growth regulator, plant growth promoting and/or yield enhancing activity: Azospirillum amazonense, A. brasilense, A. lipoferum, A. irakense, A. halopraeferens, Bradyrhizobium spp., B. elkanii, B. japonicum, B. liaoningense, B. lupini, Delftia acidovorans, Glomus intraradices, Mesorhizobium spp., Rhizobium leguminosarum bv. phaseoli R. l. bv. trifolii R. l. bv. viciae, R. tropici, Sinorhizobium melilotr;





M) Growth Regulators





    • abscisic acid (M.1.1), amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat, chlormequat chloride, choline chloride, cyclanilide, daminozide, dikegulac, dimethipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid, maleic hydrazide, mefluidide, mepiquat, mepiquat chloride, naphthaleneacetic acid, N-6-benzyladenine, paclobutrazol, prohexadione, prohexadione-calcium, prohydrojasmon, thidiazuron, triapenthenol, tributyl phosphorotrithioate, 2,3,5-tri-iodobenzoic acid, trinexapac-ethyl, uniconazole;


      N) Herbicides from Classes N.1 to N.15

    • N.1 Lipid biosynthesis inhibitors: alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofopmethyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifopbutyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-Pmethyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim, 4-(4′-chloro-4-cyclo¬propyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (1312337-72-6); 4-(2′,4′-dichloro-4-cyclopropyl[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (1312337-45-3); 4-(4′-chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (1033757-93-5); 4-(2′,4′-dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione (1312340-84-3); 5-(acetyloxy)-4-(4′-chloro-4-cyclopropy-2′-fluoro[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (1312337-48-6); 5-(acetyloxy)-4-(2′,4′-dichloro-4-cyclopropyl-[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one; 5-(acetyloxy)-4-(4′-chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (1312340-82-1); 5-(acetyloxy)-4-(2′,4′-dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (1033760-55-2); 4-(4′-chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (1312337-51-1); 4-(2′,4′-dichloro-4-cyclopropyl[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester; 4-(4′-chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (1312340-83-2); 4-(2′,4′-dichloro-4-ethyl,[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (1033760-58-5); benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, tiocarbazil, triallate, vernolate;

    • N.2 ALS inhibitors: amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsulfuronmethyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron, triflusulfuron-methyl, tritosulfuron, imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr; cloransulam, cloransulam-methyl, diclosulam, flumetsulam, florasulam, metosulam, penoxsulam, pyrimisulfan, pyroxsulam; bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid-1-methyl¬ethyl ester (420138-41-6), 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]¬methyl]amino]-benzoic acid propyl ester (420138-40-5), (4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine (420138-01-8); flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone, thiencarbazone-methyl; triafamone;

    • N.3 Photosynthesis inhibitors: amicarbazone; chlorotriazine; ametryn, atrazine, chloridazone, cyanazine, desmetryn, dimethametryn, hexazinone, metribuzin, prometon, prometryn, propazine, simazine, simetryn, terbumeton, terbuthylazin, terbutryn, trietazin; chlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron, fluometuron, isoproturon, isouron, linuron, metamitron, methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon, siduron, tebuthiuron, thiadiazuron, desmedipham, karbutilat, phenmedipham, phenmediphamethyl, bromofenoxim, bromoxynil and its salts and esters, ioxynil and its salts and esters, bromacil, lenacil, terbacil, bentazon, bentazon-sodium, pyridate, pyridafol, pentanochlor, propanil; diquat, diquat-dibromide, paraquat, paraquat-dichloride, paraquat-dimetilsulfate;

    • N.4 protoporphyrinogen-IX oxidase inhibitors: acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlormethoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, tiafenacil, trifludimoxazin, ethyl [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (353292-31-6), N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethyl¬phenoxy)-5-methyl-1H-pyrazole-1-carboxamide (452099-05-7), N-tetrahydro¬furfuryl-3-(2-chloro-6-fluoro-4-trifluoro¬methylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (452100-03-7), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione (451484-50-7), 2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1,3-dione (1300118-96-0), 1-methyl-6-trifluoro¬methyl-3-(2,2,7-tri-fluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione (1304113-05-0), methyl (E)-4-[2-chloro-5-[4-chloro-5-(difluoromethoxy)-1H-methylpyrazol-3-yl]-4-fluoro-phenoxy]-3-methoxy-but-2-enoate (948893-00-3), 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione (212754-02-4);

    • N.5 Bleacher herbicides: beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, picolinafen, 4-(3-trifluoromethyl-phenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (180608-33-7); benzobicyclon, benzofenap, bicyclopyrone, clomazone, fenquintrione, isoxaflutole, mesotrione, pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone; aclonifen, amitrole, flumeturon;

    • N.6 EPSP synthase inhibitors: glyphosate, glyphosate-isopropylammonium, glyposate-potassium, glyphosate-trimesium (sulfosate);

    • N.7 Glutamine synthase inhibitors: bilanaphos (bialaphos), bilanaphos-sodium, glufosinate, glufosinate-P, glufosinate-ammonium;

    • N.8 DHP synthase inhibitors: asulam;

    • N.9 Mitosis inhibitors: benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine, trifluralin; amiprophos, amiprophos-methyl, butamiphos; chlorthal, chlorthal-dimethyl, dithiopyr, thiazopyr, propyzamide, tebutam; carbetamide, chlorpropham, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, propham;

    • N.10 VLCFA inhibitors: acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, propisochlor, thenylchlor, flufenacet, mefenacet, diphenamid, naproanilide, napropamide, napropamide-M, fentrazamide, anilofos, cafenstrole, fenoxasulfone, ipfencarbazone, piperophos, pyroxasulfone, isoxazoline compounds of the formulae II.1, II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9







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    • N.11 Cellulose biosynthesis inhibitors: chlorthiamid, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam, 1-cyclohexyl-5-pentafluorphenyloxy-14-[1,2,4,6]thiatriazin-3-ylamine (175899-01-1);

    • N.12 Decoupler herbicides: dinoseb, dinoterb, DNOC and its salts;

    • N.13 Auxinic herbicides: 2,4-D and its salts and esters, clacyfos, 2,4-DB and its salts and esters, aminocyclopyrachlor and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifen and its salts and esters (943832-60-8); MCPA and its salts and esters, MCPAthioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, TBA (2,3,6) and its salts and esters, triclopyr and its salts and esters, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylic acid, benzyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate (1390661-72-9);

    • N.14 Auxin transport inhibitors: diflufenzopyr, diflufenzopyr-sodium, naptalam, naptalamsodium;

    • N.15 Other herbicides: bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, cyclopyrimorate (499223-49-3) and its salts and esters, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, maleic hydrazide, mefluidide, metam, methiozolin (403640-27-7), methyl azide, methyl bromide, methyldymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine, tridiphane;


      O) Insecticides from Classes O.1 to O.29

    • O.1 Acetylcholine esterase (AChE) inhibitors: aldicarb, alanycarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb, triazamate; acephate, azamethiphos, azinphos-ethyl, azinphosmethyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O-(methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, vamidothion;

    • O.2 GABA-gated chloride channel antagonists: endosulfan, chlordane; ethiprole, fipronil, flufiprole, pyrafluprole, pyriprole;

    • O.3 Sodium channel modulators: acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, kappa-bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, heptafluthrin, imiprothrin, meperfluthrin, metofluthrin, momfluorothrin, epsilon-momfluorothrin, permethrin, phenothrin, prallethrin, profluthrin, pyrethrin (pyrethrum), resmethrin, silafluofen, tefluthrin, kappa-tefluthrin, tetramethylfluthrin, tetramethrin, tralomethrin, transfluthrin; DDT, methoxychlor;

    • O.4 Nicotinic acetylcholine receptor agonists (nAChR): acetamiprid, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam; 4,5-dihydro-N-nitro-1-(2-oxiranylmethyl)-1H-imidazol-2-amine, (2E)-1-[(6-chloropyridin-3-yl)methyl]-N′-nitro-2-pentylidenehydrazinecarboximidamide; 1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridine; nicotine; sulfoxaflor, flupyradifurone, triflumezopyrim;

    • O.5 Nicotinic acetylcholine receptor allosteric activators: spinosad, spinetoram;

    • O.6 Chloride channel activators: abamectin, emamectin benzoate, ivermectin, lepimectin, milbemectin;

    • O.7 Juvenile hormone mimics: hydroprene, kinoprene, methoprene; fenoxycarb, pyriproxyfen;

    • O.8 miscellaneous non-specific (multi-site) inhibitors: methyl bromide and other alkyl halides; chloropicrin, sulfuryl fluoride, borax, tartar emetic;

    • O.9 Chordotonal organ TRPV channel modulators: pymetrozine, pyrifluquinazon; flonicamid;

    • O.10 Mite growth inhibitors: clofentezine, hexythiazox, diflovidazin; etoxazole;

    • O.11 Microbial disruptors of insect midgut membranes: Bacillus thuringiensis, Bacillus sphaericus and the insecticdal proteins they produce: Bacillus thuringiensis subsp. israelensis, Bacillus sphaericus, Bacillus thuringiensis subsp. alzawai, Bacillus thuringiensis subsp. kurstaki, Bacillus thuringiensis subsp. tenebrionis, the Bt crop proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34/35Ab1;

    • O.12 Inhibitors of mitochondrial ATP synthase: diafenthiuron; azocyclotin, cyhexatin, fenbutatin oxide, propargite, tetradifon;

    • O.13 Uncouplers of oxidative phosphorylation via disruption of the proton gradient: chlorfenapyr, DNOC, sulfluramid;

    • O.14 Nicotinic acetylcholine receptor (nAChR) channel blockers: bensultap, cartap hydrochloride, thiocyclam, thiosultap sodium;

    • O.15 Inhibitors of the chitin biosynthesis type 0: bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron;

    • O.16 Inhibitors of the chitin biosynthesis type 1: buprofezin;

    • O.17 Moulting disruptors: cyromazine;

    • O.18 Ecdyson receptor agonists: methoxyfenozide, tebufenozide, halofenozide, fufenozide, chromafenozide;

    • O.19 Octopamin receptor agonists: amitraz;

    • O.20 Mitochondrial complex III electron transport inhibitors: hydramethylnon, acequinocyl, fluacrypyrim, bifenazate;

    • O.21 Mitochondrial complex I electron transport inhibitors: fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad; rotenone;

    • O.22 Voltage-dependent sodium channel blockers: indoxacarb, metaflumizone, 2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]-hydrazinecarboxamide, N-(3-chloro-2-methylphenyl)-2-[(4-chlorophenyl)-[4-[methyl(methylsulfonyl)amino]phenyl]methylene]-hydrazinecarboxamide;

    • O.23 Inhibitors of the of acetyl CoA carboxylase: spirodiclofen, spiromesifen, spirotetramat, spiropidion;

    • O.24 Mitochondrial complex IV electron transport inhibitors: aluminium phosphide, calcium phosphide, phosphine, zinc phosphide, cyanide;

    • O.25 Mitochondrial complex II electron transport inhibitors: cyenopyrafen, cyflumetofen;

    • O.26 Ryanodine receptor-modulators: flubendiamide, chlorantraniliprole, cyantraniliprole, cyclaniliprole, tetraniliprole; (R)-3-chloro-N′-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamide, (S)-3-chloro-N′-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamide, methyl-2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]-carbonyl}amino)benzoyl]-1,2-dimethylhydrazinecarboxylate; N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; -[4,6-dichloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[4,6-dibromo-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; -[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide; 3-chloro-1-(3-chloro-2-pyridinyl)-N-[2,4-dichloro-6-[[(1-cyano-1-methylethyl)amino]carbonyl]phenyl]-1H-pyrazole-5-carboxamide; 3-bromo-N-[2,4-dichloro-6-(methylcarbamoyl)phenyl]-1-(3,5-dichloro-2-pyridyl)-1H-pyrazole-5-carboxamide; -[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide; cyhalodiamide;

    • O.27: Chordotonal organ Modulators—undefined target site: flonicamid;

    • O.28. insecticidal active compounds of unknown or uncertain mode of action: afidopyropen, afoxolaner, azadirachtin, amidoflumet, benzoximate, broflanilide, bromopropylate, chinomethionat, cryolite, dicloromezotiaz, dicofol, flufenerim, flometoquin, fluensulfone, fluhexafon, fluopyram, fluralaner, metoxadiazone, piperonyl butoxide, pyflubumide, pyridalyl, tioxazafen, 11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]-tetradec-11-en-10-one, 3-(4′-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en2-one, 1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine, Bacillus firmus I-1582; flupyrimin; fluazaindolizine; 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide; fluxametamide; 5-[3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1H-pyrazole; 4-cyano-N-[2-cyano-5-[[2,6-dibromo-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; 4-cyano-3-[(4-cyano-2-methyl-benzoyl)amino]-N-[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]-2-fluoro-benzamide; N-[5-[[2-chloro-6-cyano-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; N-[5-[[2-bromo-6-chloro-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; N-[5-[[2-bromo-6-chloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; 4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; 4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; N-[5-[[2-bromo-6-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; 2-(1,3-dioxan-2-yl)-6-[2-(3-pyridinyl)-5-thiazolyl]-pyridine; 2-[6-[2-(5-fluoro-3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine; 2-[6-[2-(3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine; N-methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide; N-methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide; 1-[(6-chloro-3-pyridinyl)methyl]-1,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro-imidazo[1,2-a]pyridine; 1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridin-5-ol; 1-isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; 1-(1,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; N,5-dimethyl-N-pyridazin-4-yl-1-(2,2,2-trifluoro-1-methyl-ethyl)pyrazole-4-carboxamide; 1-[1-(1-cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; N-ethyl-1-(2-fluoro-1-methyl-propyl)-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; 1-(1,2-dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; 1-[1-(1-cyanocyclopropyl)ethyl]-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; N-methyl-1-(2-fluoro-1-methyl-propyl]-5-methyl-1-pyridazin-4-yl-pyrazole-4-carboxamide; 1-(4,4-difluorocyclohexyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; 1-(4,4-difluorocyclohexyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide, N-(1-methylethyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide; N-cyclopropyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide; N-cyclohexyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide; 2-(3-pyridinyl)-N-(2,2,2-trifluoroethyl)-2H-indazole-4-carboxamide; 2-(3-pyridinyl)-N-[(tetrahydro-2-furanyl)methyl]-2H-indazole-5-carboxamide; methyl 2-[[2-(3-pyridinyl)-2H-indazol-5-yl]carbonyl]hydrazinecarboxylate; -[(2,2-difluorocyclopropyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide; N-(2,2-difluoropropyl)-2-(3-pyridinyl)-2H-indazole-5-carboxamide; 2-(3-pyridinyl)-N-(2-pyrimidinylmethyl)-2H-indazole-5-carboxamide; N-[(5-methyl-2-pyrazinyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide, tyclopyrazoflor; sarolaner, lotilaner, N-[4-chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1-methyl-3-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide; M.UN.22a 2-(3-ethylsulfonyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo-isoxazolidin-4-yl]-2-methyl-benzamide, 4-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-MA[(4R)-2-ethyl-3-oxoisoxazolidin-4-yl]-2-methyl-benzamide; A[4-chloro-3-(cyclopropylcarbamoyl)phenyl]-2-methyl-5-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazole-3-carboxamide, N-[4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl]-2-methyl-5-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazole-3-carboxamide; acynonapyr; benzpyrimoxan; chloro-N-(1-cyanocyclopropyl)-5-[1-[2-methyl-5-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide, oxazosulfyl, [(2S,3R,4R,5S,6S)-3,5-dimethoxy-6-methyl-4-propoxy-tetrahydropyran-2-yl]-MA[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate, [(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl] N-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate, [(2S,3R,4R,5S,6S)-3,5-dimethoxy-6-methyl-4-propoxy-tetrahydropyran-2-yl]-N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate, [(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl]-A[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate, (22)-3-(2-isopropylphenyl)-2-[(E)-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]methylenehydrazono]thiazolidin-4-one.





a


The active substances referred to as component 2, their preparation and their activity e. g. against harmful fungi is known (cf.: http://www.alanwood.net/pesticides/); these substances are commercially available. The compounds described by IUPAC nomenclature, their preparation and their pesticidal activity are also known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968; EP-A 141 317; EP-A 152 031; EP-A 226 917; EP-A 243 970; EP-A 256 503; EP-A 428 941; EP-A 532 022; EP-A 1 028 125; EP-A 1 035 122; EP-A 1 201 648; EP-A 1 122 244, JP 2002316902; DE 19650197; DE 10021412; DE 102005009458; U.S. Pat. Nos. 3,296,272; 3,325,503; WO 98/46608; WO 99/14187; WO 99/24413; WO 99/27783; WO 00/29404; WO 00/46148; WO 00/65913; WO 01/54501; WO 01/56358; WO 02/22583; WO 02/40431; WO 03/10149; WO 03/11853; WO 03/14103; WO 03/16286; WO 03/53145; WO 03/61388; WO 03/66609; WO 03/74491; WO 04/49804; WO 04/83193; WO 05/120234; WO 05/123689; WO 05/123690; WO 05/63721; WO 05/87772; WO 05/87773; WO 06/15866; WO 06/87325; WO 06/87343; WO 07/82098; WO 07/90624, WO 10/139271, WO 11/028657, WO 12/168188, WO 07/006670, WO 11/77514; WO 13/047749, WO 10/069882, WO 13/047441, WO 03/16303, WO 09/90181, WO 13/007767, WO 13/010862, WO 13/127704, WO 13/024009, WO 13/24010, WO 13/047441, WO 13/162072, WO 13/092224, WO 11/135833, CN 1907024, CN 1456054, CN 103387541, CN 1309897, WO 12/84812, CN 1907024, WO 09094442, WO 14/60177, WO 13/116251, WO 08/013622, WO 15/65922, WO 94/01546, EP 2865265, WO 07/129454, WO 12/165511, WO 11/081174, WO 13/47441). Some compounds are identified by their CAS Registry Number which is separated by hyphens into three parts, the first consisting from two up to seven digits, the second consisting of two digits, and the third consisting of a single digit.


The present invention furthermore relates to agrochemical compositions comprising a mixture of at least one compound I (component 1) and at least one further active substance useful for plant protection, e. g. selected from the groups A) to O) (component 2), in particular one further fungicide, e. g. one or more fungicide from the groups A) to K), as described above, and if desired one suitable solvent or solid carrier. Those mixtures are of particular interest, since many of them at the same application rate show higher efficiencies against harmful fungi. Furthermore, combating harmful fungi with a mixture of compounds I and at least one fungicide from groups A) to K), as described above, is more efficient than combating those fungi with individual compounds I or individual fungicides from groups A) to K).


By applying compounds I together with at least one active substance from groups A) to O) a synergistic effect can be obtained, i.e. more then simple addition of the individual effects is obtained (synergistic mixtures).


This can be obtained by applying the compounds I and at least one further active substance simultaneously, either jointly (e. g. as tank-mix) or separately, or in succession, wherein the time interval between the individual applications is selected to ensure that the active substance applied first still occurs at the site of action in a sufficient amount at the time of application of the further active substance(s). The order of application is not essential for working of the present invention.


When applying compound I and a pesticide II sequentially the time between both applications may vary e. g. between 2 hours to 7 days. Also a broader range is possible ranging from 0.25 hour to 30 days, preferably from 0.5 hour to 14 days, particularly from 1 hour to 7 days or from 1.5 hours to 5 days, even more preferred from 2 hours to 1 day. In case of a mixture comprising a pesticide II selected from group L), it is preferred that the pesticide II is applied as last treatment.


According to the invention, the solid material (dry matter) of the biopesticides (with the exception of oils such as Neem oil) are considered as active components (e. g. to be obtained after drying or evaporation of the extraction or suspension medium in case of liquid formulations of the microbial pesticides).


In accordance with the present invention, the weight ratios and percentages used herein for a biological extract such as Quillay extract are based on the total weight of the dry content (solid material) of the respective extract(s).


The total weight ratios of compositions comprising at least one microbial pesticide in the form of viable microbial cells including dormant forms, can be determined using the amount of CFU of the respective microorganism to calculate the total weight of the respective active component with the following equation that 1×1010 CFU equals one gram of total weight of the respective active component. Colony forming unit is measure of viable microbial cells, in particular fungal and bacterial cells. In addition, here “CFU” may also be understood as the number of (juvenile) individual nematodes in case of (entomopathogenic) nematode biopesticides, such as Steinernema fetiae.


In the binary mixtures and compositions according to the invention the weight ratio of the component 1) and the component 2) generally depends from the properties of the active components used, usually it is in the range of from 1:10,000 to 10,000:1, often it is in the range of from 1:100 to 100:1, regularly in the range of from 1:50 to 50:1, preferably in the range of from 1:20 to 20:1, more preferably in the range of from 1:10 to 10:1, even more preferably in the range of from 1:4 to 4:1 and in particular in the range of from 1:2 to 2:1.


According to further embodiments of the binary mixtures and compositions, the weight ratio of the component 1) and the component 2) usually is in the range of from 1000:1 to 1:1, often in the range of from 100:1 to 1:1, regularly in the range of from 50:1 to 1:1, preferably in the range of from 20:1 to 1:1, more preferably in the range of from 10:1 to 1:1, even more preferably in the range of from 4:1 to 1:1 and in particular in the range of from 2:1 to 1:1.


According to further embodiments of the mixtures and compositions, the weight ratio of the component 1) and the component 2) usually is in the range of from 20,000:1 to 1:10, often in the range of from 10,000:1 to 1:1, regularly in the range of from 5,000:1 to 5:1, preferably in the range of from 5,000:1 to 10:1, more preferably in the range of from 2,000:1 to 30:1, even more preferably in the range of from 2,000:1 to 100:1 and in particular in the range of from 1,000:1 to 100:1.


According to a further embodiments of the binary mixtures and compositions, the weight ratio of the component 1) and the component 2) usually is in the range of from 1:1 to 1:1000, often in the range of from 1:1 to 1:100, regularly in the range of from 1:1 to 1:50, preferably in the range of from 1:1 to 1:20, more preferably in the range of from 1:1 to 1:10, even more preferably in the range of from 1:1 to 1:4 and in particular in the range of from 1:1 to 1:2.


According to further embodiments of the mixtures and compositions, the weight ratio of the component 1) and the component 2) usually is in the range of from 10:1 to 1:20,000, often in the range of from 1:1 to 1:10,000, regularly in the range of from 1:5 to 1:5,000, preferably in the range of from 1:10 to 1:5,000, more preferably in the range of from 1:30 to 1:2,000, even more preferably in the range of from 1:100 to 1:2,000 to and in particular in the range of from 1:100 to 1:1,000.


In the ternary mixtures, i.e. compositions according to the invention comprising the component 1) and component 2) and a compound III (component 3), the weight ratio of component 1) and component 2) depends from the properties of the active substances used, usually it is in the range of from 1:100 to 100:1, regularly in the range of from 1:50 to 50:1, preferably in the range of from 1:20 to 20:1, more preferably in the range of from 1:10 to 10:1 and in particular in the range of from 1:4 to 4:1, and the weight ratio of component 1) and component 3) usually it is in the range of from 1:100 to 100:1, regularly in the range of from 1:50 to 50:1, preferably in the range of from 1:20 to 20:1, more preferably in the range of from 1:10 to 10:1 and in particular in the range of from 1:4 to 4:1.


Any further active components are, if desired, added in a ratio of from 20:1 to 1:20 to the component 1).


These ratios are also suitable for inventive mixtures applied by seed treatment.


When mixtures comprising microbial pesticides are employed in crop protection, the application rates preferably range from about 1×106 to 5×1016 (or more) CFU/ha, preferably from about 1×108 to about 1×1013 CFU/ha, and even more preferably from about 1×109 to 5×1015 CFU/ha and particularly preferred even more preferably from 1×1012 to 5×1014 CFU/ha. In the case of (entomopathogenic) nematodes as microbial pesticides (e. g. Steinernema feltiae), the application rates preferably range inform about 1×105 to 1×1012 (or more), more preferably from 1×108 to 1×1011, even more preferably from 5×108 to 1×1010 individuals (e. g. in the form of eggs, juvenile or any other live stages, preferably in an infective juvenile stage) per ha.


When mixtures comprising microbial pesticides are employed in seed treatment, the application rates with respect to plant propagation material preferably range from about 1×106 to 1×1012 (or more) CFU/seed. Preferably, the concentration is about 1×106 to about 1×109 CFU/seed. In the case of the microbial pesticides II, the application rates with respect to plant propagation material also preferably range from about 1×107 to 1×1014 (or more) CFU per 100 kg of seed, preferably from 1×109 to about 1×1012 CFU per 100 kg of seed.


Preference is also given to mixtures comprising as component 2) at least one active substance selected from inhibitors of complex III at Q0 site in group A), more preferably selected from compounds (A.1.1), (A.1.4), (A.1.8), (A.1.9), (A.1.10), (A.1.12), (A.1.13), (A.1.14), (A.1.17), (A.1.21), (A.1.25), (A.1.34) and (A.1.35); particularly selected from (A.1.1), (A.1.4), (A.1.8), (A.1.9), (A.1.13), (A.1.14), (A.1.17), (A.1.25), (A.1.34) and (A.1.35).


Preference is also given to mixtures comprising as component 2) at least one active substance selected from inhibitors of complex III at Qi site in group A), more preferably selected from compounds (A.2.1), (A.2.3) and (A.2.4); particularly selected from (A.2.3) and (A.2.4).


Preference is also given to mixtures comprising as component 2) at least one active substance selected from inhibitors of complex II in group A), more preferably selected from compounds (A.3.2), (A.3.3), (A.3.4), (A.3.7), (A.3.9), (A.3.11), (A.3.12), (A.3.15), (A.3.16), (A.3.17), (A.3.18), (A.3.19), (A.3.20), (A.3.21), (A.3.22), (A.3.23), (A.3.28), (A.3.31), (A.3.32), (A.3.33), (A.3.34), (A.3.35), (A.3.36), (A.3.37), (A.3.38) and (A.3.39); particularly selected from (A.3.2), (A.3.3), (A.3.4), (A.3.7), (A.3.9), (A.3.12), (A.3.15), (A.3.17), (A.3.19), (A.3.22), (A.3.23), (A.3.31), (A.3.32), (A.3.33), (A.3.34), (A.3.35), (A.3.36), (A.3.37), (A.3.38) and (A.3.39).


Preference is also given to mixtures comprising as component 2) at least one active substance selected from other respiration inhibitors in group A), more preferably selected from compounds (A.4.5) and (A.4.11); in particular (A.4.11).


Preference is also given to mixtures comprising as component 2) at least one active substance selected from C14 demethylase inhibitors in group B), more preferably selected from compounds (B.1.4), (B.1.5), (B.1.8), (B.1.10), (B.1.11), (B.1.12), (B.1.13), (B.1.17), (B.1.18), (B.1.21), (B.1.22), (B.1.23), (B.1.25), (B.1.26), (B.1.29), (B.1.34), (B.1.37), (B.1.38), (B.1.43) and (B.1.46); particularly selected from (B.1.5), (B.1.8), (B.1.10), (B.1.17), (B.1.22), (B.1.23), (B.1.25), (B.1.33), (B.1.34), (B.1.37), (B.138), (B.1.43) and (B.1.46).


Preference is also given to mixtures comprising as component 2) at least one active substance selected from Delta14-reductase inhibitors in group B), more preferably selected from compounds (B.2.4), (B.2.5), (B.2.6) and (B.2.8); in particular (B.2.4).


Preference is also given to mixtures comprising as component 2) at least one active substance selected from phenylamides and acyl amino acid fungicides in group C), more preferably selected from compounds (C.1.1), (C.1.2), (C.1.4) and (C.1.5); particularly selected from (C.1.1) and (C.1.4).


Preference is also given to mixtures comprising as component 2) at least one active substance selected from other nucleic acid synthesis inhibitors in group C), more preferably selected from compounds (C.2.6), (C.2.7) and (C.2.8).


Preference is also given to mixtures comprising as component 2) at least one active substance selected from group D), more preferably selected from compounds (D.1.1), (D.1.2), (D.1.5), (D.2.4) and (D.2.6); particularly selected from (D.1.2), (D.1.5) and (D.2.6).


Preference is also given to mixtures comprising as component 2) at least one active substance selected from group E), more preferably selected from compounds (E.1.1), (E.1.3), (E.2.2) and (E.2.3); in particular (E.1.3).


Preference is also given to mixtures comprising as component 2) at least one active substance selected from group F), more preferably selected from compounds (F.1.2), (F.1.4) and (F.1.5).


Preference is also given to mixtures comprising as component 2) at least one active substance selected from group G), more preferably selected from compounds (G.3.1), (G.3.3), (G.3.6), (G.5.1), (G.5.2), (G.5.3), (G.5.4), (G.5.5), G.5.6), G.5.7), (G.5.8), (G.5.9), (G.5.10) and (G.5.11); particularly selected from (G.3.1), (G.5.1), (G.5.2) and (G.5.3).


Preference is also given to mixtures comprising as component 2) at least one active substance selected from group H), more preferably selected from compounds (H.2.2), (H.2.3), (H.2.5), (H.2.7), (H.2.8), (H.3.2), (H.3.4), (H.3.5), (H.4.9) and (H.4.10); particularly selected from (H.2.2), (H.2.5), (H.3.2), (H.4.9) and (H.4.10).


Preference is also given to mixtures comprising as component 2) at least one active substance selected from group 1), more preferably selected from compounds (1.2.2) and (1.2.5).


Preference is also given to mixtures comprising as component 2) at least one active substance selected from group J), more preferably selected from compounds (J.1.2), (J.1.5), (J.1.8), (J.1.11) and (J.1.12); in particular (J.1.5).


Preference is also given to mixtures comprising as component 2) at least one active substance selected from group K), more preferably selected from compounds (K.1.41), (K.1.42), (K.1.44) and (K.1.47); particularly selected from (K.1.41), (K.1.44) and (K.1.47).







SYNTHESIS EXAMPLE

With due modification of the starting compounds, the procedures shown in the synthesis examples below were used to obtain further compounds I. The resulting compounds, together with physical data, are listed in Table I below.


HPLC-MS: HPLC-column Kinetex XB C18 1.7μ (50×2.1 mm); eluent: acetonitrile/water+0.1% TFA (5 gradient from 5:95 to 100:0 in 1.5 min at 60° C., flow gradient from 0.8 to 1.0 ml/min in 1.5 min). MS: Quadrupol Electrospray Ionisation, 80 V (positive mode).


1. Synthesis of Intermediate Ethyl 2-benzyl-4-methyl-pentanoate



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Under inert atmosphere, lithium diisopropylamide (4.457 g, 32 mmol) was dissolved in THF (250 mL) and cooled to −78° C. Ethyl-4-methylvalerate (5.000 g, 35 mmol) was added dropwise and stirred at −78° C. for 2 h. Benzyl bromide (7.116 g, 41.6 mmol) was added dropwise, stirred at −78° C. for 1 h and subsequently for 2 h at 25° C. Aq. sat. NH4Cl solution was added and the organic phase was extracted with MTBE, washed with water and brine, dried over MgSO4, and evaporated. Column chromatography (SiO2; cyclohexane/ethyl acetate 2:1) yielded ethyl 2-benzyl-4-methyl-pentanoate (8.100 g, quant.) as colorless powder.


2. Synthesis of Intermediate Ethyl 2-benzyl-2,4-dimethyl-pentanoate



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Under inert atmosphere, lithium diisopropylamide (3.456 g, 42 mmol) was dissolved in THF (40 mL) and cooled to −78° C. Ethyl 2-benzyl-4-methyl-pentanoate (6.300 g, 26.9 mmol) was dissolved in THF (10 mL), added dropwise, and stirred at −78° C. for 2 h. Methyl iodide (4.579 g, 32 mmol) was added dropwise, stirred at −78° C. for 10 min and subsequently for 2 h at 25° C. Aq. sat. NH4Cl solution was added and the organic phase was extracted with MTBE, washed with water and brine, dried over MgSO4, and evaporated. Column chromatography (SiO2; cyclohexane/ethyl acetate 2:1) yielded Intermediate ethyl 2-benzyl-2,4-dimethyl-pentanoate (6.300 g, 94%) as colorless powder.


3. Synthesis of Intermediate 2-benzyl-2,4-dimethyl-pentanoic acid



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Ethyl 2-benzyl-2,4-dimethyl-pentanoate (6.300 g, 25.4 mmol) was dissolved in dioxane/EtOH 1:1 (30 mL). Aq. 2 M NaOH solution (25 mL) was added and the mixture was stirred at 120° C. over night. The organic solvents were evaporated, the mixture was taken up in water and washed with cyclohexane. The aq. phase was adjusted to pH=1 with HCl and extracted with dichloromethane. The combined organic phases were washed with water and brine, dried over MgSO4, and evaporated to yield 2-benzyl-2,4-dimethyl-pentanoic acid (650 mg, 12%) as colorless powder.


Synthesis of Intermediate 2-benzyl-2,4-dimethyl-pentanoyl Chloride



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Under inert atmosphere, 2-benzyl-2,4-dimethyl-pentanoic acid (650 mg, 3 mmol) was dissolved in thionyl chloride (6 mL), stirred at 95° C. for 3 h, and evaporated to yield 2-benzyl-2,4-dimethyl-pentanoyl chloride (690 mg, 98%) as a brown oil.


4. Synthesis of Ex-80

Under inert atmosphere, 5,6-dimethyl-3-amino-pyridine (512 mg, 4.2 mmol) was dissolved in dichloromethane (15 mL) and treated with NEt3 (424 mg, 4.2 mmol). The mixture was cooled to 0° C., treated with a solution of 2-benzyl-2,4-dimethyl-pentanoyl chloride (553 mg, 2.3 mmol) in dichloromethane (3 mL), stirred at 0° C. for 20 min and subsequently at 25° C. over night. Water was added and phases were separated. The aq. phase was extracted with dichloromethane and the combined organic phases were washed with aq. sat. NH4Cl solution, aq. sat. NaHCO3 solution, and brine, dried over MgSO4, and evaporated. Column chromatography (SiO2; cyclohexane/ethyl acetate 2:1) yielded Target Molecule Ex-80 (550 mg, 73%) as colorless powder.









TABLE I







Compounds Ex-1 to Ex-81 of the formula I.A-1









I.A-1




embedded image


























Melting
HPLC


Ex.





Point
Rt


no
R2
R3
R6
R7
R8
(° C.)
(min)*/**





Ex-1
—CH3
—CH3

t-butyl
H
—CH2Ph
169
0.91*


Ex-2
—CH3
—CH3
—CH3
H
—CH2Ph
103
 0.79**


Ex-3
—CH3
—CH3
—CH3
H
—Ph
168
0.85*


Ex-4
—CH3
—CH3
—CH2CH3
H
—Ph
126
0.84*


Ex-5
—CH3
—CH3
—CH(CH3)2
H
—Ph
160
 0.87**


Ex-6
—CH3
—CH3
—CH2CH2CH3
H
—Ph
130
 0.87**


Ex-7
—CH3
—CH3
—CH2CH(CH3)2
H
—Ph
136
 0.94**


Ex-8
—CH3
—CH3
—CH2CH3
H
—CH2Ph
nd
 0.84**


Ex-9
—CH3
—CH3
—CH(CH3)2
H
—CH2Ph
nd
 0.88**


Ex-10
—CH3
—CH3
—CH2CH2CH3
H
—CH2Ph
nd
 0.91**


Ex-11
—CH3
—CH3
—O—t-butyl
H
—Ph
142
 0.90**


Ex-12
—CH3
—CH3

t-butyl
H
—Ph
159
 0.98**


Ex-13
—CH3
—CH3
—CH2CH(CH3)2
H
—CH2Ph
121
 0.98**


Ex-14
—CH3
—CH3
—CH(CH3)2
H
—CH2CH2Ph
nd
 0.97**


Ex-15
—CH3
—CH3
—CH2CH(CH3)2
H
—CH2CH2Ph
83
 1.03**


Ex-16
—CH3
—CH3

t-butyl
H
—CH2CH2Ph
174
 0.98**


Ex-17
—CH3
—CH3
—CH2CH2CH3
H
—CH2CH2Ph
nd
 0.94**


Ex-18
—CH3
—CH3
—CH2CH3
H
—CH2CH2Ph
150
 0.92**


Ex-19
—CH3
—CH3
—CH3
OH
—Ph
158
 0.72**


Ex-20
—CH3
—CH3
—CH2CH(CH3)2
OH
—Ph
nd
 0.91**


Ex-21
—CH3
—CH3
—CH2CH2CH3
OH
—Ph
145
 0.85**


Ex-22
—CH3
—CH3
—CH(CH3)2
OH
—Ph
nd
 0.85**


Ex-23
—CH3
—CH3
—CH2CH3
OH
—CH2Ph
nd
 0.79**


Ex-24
—CH3
—CH3
H
H
—Ph
113
0.70*


Ex-25
—CH3
—CH3
F
F
—Ph
143
0.78*


Ex-26
—CH3
—CH3
—CH3
—CH3
—Ph
144
0.81*


Ex-27
—CH3
—CHF2
H
H
—Ph
113
1.01*


Ex-28
—CH3
—CH3
—CH3
—CH3
—CH2CH3
nd
0.70*


Ex-29
—CH3
—CH3
—CH3
—CH3
—CH2CH2CH3
nd
0.78*


Ex-30
—CH3
—CH3
—CH3
—CH3
—CH2CH2CH2CH3
nd
0.85*


Ex-31
—CH3
—CH3
—CH3
—CH3
—CH2Ph
98
0.83*


Ex-32
—CH3
—CH3
—CH3
—CH3
—CH(CH3)2
nd
0.79*


Ex-33
—CH3
—CH3
—CH3
—CH3

t-butyl
110
0.82*


Ex-34
—CH3
—CH3
H
H
—CH2Ph
129
0.74*


Ex-35
—CH3
—CH3
H
H
—CH2CH2Ph
nd
0.79*


Ex-36
—CH3
—CH3
—CH3
—CH3
cyclopropyl
nd
0.73*


Ex-37
—CH3
—CH3
F
F
—Ph
117
1.08*


Ex-38
—CH3
—CH3

t-butyl
H
—CH2Ph
169
0.91*


Ex-39
—CH3
—CH3
—CH3
H
—CH2Ph
103
0.79*


Ex-40
—CH3
—CHF2
—CH3
—CH3
—Ph
108
1.13*


Ex-41
—CH3
—CH3
—CH3
H
—Ph
168
0.84*


Ex-42
—CH3
—CHF2

t-butyl
H
—CH2Ph
nd
1.25*


Ex-43
—CH3
—CH3
H
H
—CH2—cyclohexyl
nd
0.94*


Ex-44
—CH3
—CH3
—CH(CH3)2
H
Br
nd
0.82*


Ex-45
—CH3
—CH3
—CH2CH2CH2CH3
H
Phenyl
nd
0.99*


Ex-46
—CH3
—CH3
cyclopentyl
H
Phenyl
nd
0.99*


Ex-47
—CH3
—CH3
H
H

nd
0.89*


Ex-48
—CH3
—CH3
H
H

nd
0.89*


Ex-49
—CH3
—CH3
H
H

nd
0.91*


Ex-50
—CH3
—CH3
—CH3
H
—CH2CH2CH2CH2CH3
nd
0.93*


Ex-51
—CH3
—CH3
H
H
3,4-dichlorophenyl
nd
0.92*


Ex-52
—CH3
—CH3
H
H

nd
0.87*


Ex-53
—CH3
—CH3
—CH2CH2CH3
H
—CH2CH2CH3
nd
0.91*


Ex-54
—CH3
—CH3
—CH2Ph
H

nd
0.93*


Ex-55
—CH3
—CH3
—CN
H

nd
0.81*


Ex-56
—CH3
—CH3
—CH(CH3)2
H
—CH2CH2CH(CH3)2
nd
1.00*


Ex-57
—CH3
—CH3
H
H
—CH2—cyclopentyl
nd
0.90*


Ex-58
—CH3
—CH3
H
H

nd
0.88*


Ex-59
—CH3
—CH3
H
H

nd
0.99*


Ex-60
—CH3
—CH3
H
H

nd
0.88*


Ex-61
—CH3
—CH3
H
H

nd
0.74*


Ex-62
—CH3
—CH3
H
H

nd
0.84*


Ex-63
—CH3
—CH3
—CF3
—OCH3
phenyl
nd
0.94*


Ex-64
—CH3
—CH3
H
H
-cyclohexyl
nd
0.87*


Ex-65
—CH3
—CH3
H
Cl
—CH2Cl
nd
0.70*


Ex-66
—CH3
—CH3
—CH3
—CH3

nd
0.77*


Ex-67
—Cl
—Cl
H
H
4-trifluoromethylphenyl
nd
1.24*


Ex-68
H
—N(CH3)2
H
H
4-trifluoromethylphenyl
nd
0.82*


Ex-69
—CH3
—CHF2
cyclopropyl
H
—CH2Ph
nd
1.18*


Ex-70
—CH3
—CH3
cyclopropyl
H
—CH2Ph
nd
0.84*


Ex-71
H
—N(CH3)2
—CH(CH3)2
H
4-methoxyphenyl
nd
0.91*


Ex-72
H
—OCH3
—CH(CH3)2
H
4-methoxyphenyl
nd
1.05*


Ex-73
H
—SCH3
—CH(CH3)2
H
4-methoxyphenyl
nd
1.10*


Ex-74
—Cl
—Cl
—CH(CH3)2
H
4-methoxyphenyl
nd
1.31*


Ex-75
—CH3
—CH3
—CH(CH3)2
H
4-methoxyphenyl
nd
0.90*


Ex-76
—CH3
—CHF2
—CH(CH3)2
H
4-methoxyphenyl
nd
1.24*


Ex-77
—CH3
—CF3
—CH(CH3)2
H
4-methoxyphenyl
nd
1.32*


Ex-78
H
—Cl
—CH(CH3)2
H
4-methoxyphenyl
nd
1.21*


Ex-79
—OCH3
—OCH3
—CH(CH3)2
H
4-methoxyphenyl
nd
1.13*


Ex-80
—CH3
—CH3
—CH2CH(CH3)2
—CH3
—CH2Ph
123
1.01*


Ex-81
—CH3
—CHF2
—CH2CH(CH3)2
—CH3
—CH2Ph
112
1.32*
















TABLE 2







Compounds Ex-82 to Ex-96 of the formula I.A-2




















Melting
HPLC








Point
Rt


Ex. no.
R2
R3
R6
R7
R8
(° C.)
(min)*/**





Ex-82
—CH3
—CH3
—CH3
—CH3
—CH3
104
0.66*


Ex-83
—CH3
—CH3
H
H
—Ph
172
0.69*


Ex-84
—CH3
—CH3
—CH3
—CH3
—CH2CH3
 98
0.69*


Ex-85
—CH3
—CH3
F
F
—Ph
 99
0.76*


Ex-86
—CH3
—CH3
—CH3
—CH3
—CH2CH2CH3
nd
0.79*


Ex-87
—CH3
—CH3
—CH3
—CH3
—Ph
104
0.79*


Ex-88
—CH3
—CH3
—CH3
—CH3
—CH2CH2CH2CH3
nd
0.86*


Ex-89
—CH3
—CH3
—CH3
—CH3
—CH2Ph
nd
0.85*


Ex-90
—CH3
—CH3
—CH3
—CH3
—CH(CH3)2
131
0.77*


Ex-91
—CH3
—CH3
H
H
—CH2Ph
184
0.74*


Ex-92
—CH3
—CH3
H
H
—CH2CH2Ph
nd
0.83*


Ex-93
—CH3
—CH3
—CH3
—CH3

t-Butyl
156
0.82*


Ex-94
—CH3
—CH3
H

t-Butyl
—CH2Ph
149
0.91*


Ex-95
—CH3
—CH3
—CH3
—CH3
cyclopropyl
nd
0.71*


Ex-96
—CH3
—CH3
H
—CH3
—CH2Ph
218
0.73*





*Standart 100_700


**pos_Standard


HPLC: High Performance Liquid Chromatography; HPLC-column Kinetex XB C18 1.7μ (50 × 2.1 mm); eluent: acetonitrile/water + 0.1% trifluoroacetic acid (gradient from 5:95 to 100:0 in 1.5 min at 60° C., flow gradient from 0.8 to 1.0 ml/min in 1.5 min). MS: Quadrupol Electrospray lonisation, 80 V (positive mode). Rt: retention time i






II. Biological Trials


Microtest


The active compounds were formulated separately as a stock solution having a concentration of 10000 ppm in dimethyl sulfoxide.


EXAMPLE 1
Activity Against the Grey Mold Botrytis cinerea in the Microtiterplate Test

The stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of Botrci cinerea in an aqueous biomalt or yeast-bactopeptone-sodiumacetate or DOB solution was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18° C. Using an absorption photometer, the MTPs were measured at 405 nm 7 days after the inoculation.


In this test, the samples which had been treated with 31 ppm of the active substance from examples Ex-12, Ex-14, Ex-16, Ex-33, Ex-38, Ex-42, Ex-56, Ex-63, Ex-70, Ex-74, Ex-76, Ex-77, Ex-80 and Ex-88 respectively, showed up to at most 11% growth of the pathogen.


EXAMPLE 2
Activity Against Fusarium culmorum in the Microtiterplate Test

The stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of Fusarium culmorum in an aqueous biomalt or yeast-bactopeptone-glycerine or DOB solution was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18° C. Using an absorption photometer, the MTPs were measured at 405 nm 7 days after the inoculation.


In this test, the samples which had been treated with 31 ppm of the active substance from examples Ex-4, Ex-5, Ex-6, Ex-7, Ex-12, Ex-12, Ex-13, Ex-14, Ex-15, Ex-16, Ex-17, Ex-18, Ex-25, Ex-33, Ex-35, Ex-41, Ex-43, Ex-44, Ex-45, Ex-46, Ex-47, Ex-49, Ex-50, Ex-53, Ex-56, Ex-57, Ex-59, Ex-63, Ex64, Ex-70, Ex-74, Ex-80 and Ex-88 respectively, showed up to at most 15% growth of the pathogen.


EXAMPLE-3
Activity Against Rice Blast Pyricularia oryzae in the Microtiterplate Test

The stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of Pyricularia oryzae in an aqueous biomalt or yeast-bactopeptone-glycerine or DOB solution was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18° C. Using an absorption photometer, the MTPs were measured at 405 nm 7 days after the inoculation.


The measured parameters were compared to the growth of the active compound-free control variant (100%) and the fungus-free and active compound-free blank value to determine the relative growth in % of the pathogens in the respective active compounds.


In this test, the samples which had been treated with 31 ppm of the active substance from examples Ex-30, Ex-31, Ex-32, Ex-33, Ex-35, Ex-38, Ex-42, Ex-49, Ex-50, Ex-51, Ex-52, Ex-56, Ex-59, Ex-63, Ex-80, Ex-81, Ex-84, Ex-85, Ex-87, Ex-88, Ex-90, Ex-93, Ex-94, Ex-95 and Ex-96 respectively, showed up to at most 15% growth of the pathogen.


Green House


The Spray Solutions were Prepared in Several Steps:


The stock solution was prepared: a mixture of acetone and/or dimethylsulfoxide and the wetting agent/emulsifier Wettol, which is based on ethoxylated alkylphenoles, in a relation (volume) solvent-emulsifier of 99 to 1 was added to the initial weight of the compound to give a total of 5 ml. Water was then added to total volume of 100 ml.


This stock solution was diluted with the described solvent-emulsifier-water mixture to the given concentration.


Preventative Fungicidal Control of Botrytis cinerea on Leaves of Green Pepper


Young seedlings of green pepper were grown in pots to the 4 to 5 leaf stage. These plants were sprayed to run-off with an aqueous suspension, containing the concentration of active ingredient or their mixture mentioned in the table below. The next day the plants were inoculated with an aqueous biomalt or DOB solution containing the spore suspension of Botrytis cinerea. Then the plants were immediately transferred to a humid chamber. After 5 days at 22 to 24⋅ C and a relative humidity close to 100% the extent of fungal attack on the leaves was visually assessed as % diseased leaf area.


In this test, the samples which had been treated with 250 ppm of the active substance from examples from Ex-33, Ex-36, Ex-38, Ex-42, Ex-80 and Ex-94 respectively, showed up to at most 15% growth of the pathogen whereas the untreated plants were 90% infected.

Claims
  • 1. A compound of formula I
  • 2. The compound of claim 1, wherein R1 is H, F, Cl, Br, CN, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C3-C6-cycloalkyl, wherein the acyclic moieties of R1 are unsubstituted or substituted by halogen.
  • 3. The compound of claim 1, wherein R2 is selected from CN, halogen, C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkynyl, ORY, C3-C6-cycloalkyl, wherein RY is C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl or C2-C6-alkynyl.
  • 4. The compound of claim 1, wherein R3 is selected from CN, halogen, C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkynyl, ORY, C3-C6-cycloalkyl, wherein RY is C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl or C2-C6-alkynyl.
  • 5. The compound of claim 1, wherein R4 is H, F, Cl, Br, CN, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C3-C6-cycloalkyl, wherein the acyclic moieties of R1 are unsubstituted or substituted by halogen.
  • 6. The compound of claim 1, wherein R5 is H.
  • 7. The compound of claim 1, wherein R6 is selected from CN, C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C3-C6-cycloalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C1-C6-alkoxy, C3-C6-cycloalkynyl, C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), CR′═NOR″, a saturated three-, four-, five-, six-, membered carbocycle or heterocycle, a five- or six-membered heteroaryl, benzyl or aryl.
  • 8. The compound of claim 1, wherein R7 and R8 are independently selected from CN, C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C3-C6-cycloalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C1-C6-alkoxy, C3-C6-cycloalkynyl, C(═O)C1-C6-alkyl, C(═O)O(C1-C6-alkyl), CR′═NOR″, a saturated three-, four-, five-, six-, membered carbocycle or heterocycle, a five- or six-membered heteroaryl, benzyl or aryl.
  • 9. The compound of formula I as defined in claim 1, whereinX is O,R1 is H,R2 is C1-C6-alkyl and C1-C6-halogenalkyl,R3 is C1-C6-alkyl and C1-C6-halogenalkyl,R4 is H, andR5 is H.
  • 10. The compound of formula I as defined in claim 1, whereinX is O,R1 is in each case independently selected from CN, COOH, CONH2, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein Rx is C1-C4-alkyl, C1-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted by 1, 2, 3, 4 or 5 substituents R′ independently selected from C1-C4-alkyl, halogen, OH, CN, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy;wherein the acyclic moieties of R1 are unsubstituted or substituted with identical or different groups R1a which independently of one another are selected from:R1a halogen, OH, CN, COOH, CONH2, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy, C1-C6-alkylthio, aryl and phenoxy, wherein the aryl group is unsubstituted or carries 1, 2, 3, 4 or 5 substituents R11a selected from the group consisting of halogen, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy;wherein the carbocyclic, heteroaryl and aryl moieties of R1 are not further substituted or carry 1, 2, 3, 4, 5 or up to the maximum number of identical or different groups R1b which independently of one another are selected from:R1b halogen, OH, CN, COOH, CONH2, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy and C1-C6-alkylthio;R2 is C1-C6-alkyl and C1-C6-halogenalkyl,R3 is C1-C6-alkyl and C1-C6-halogenalkyl,R4 is is in each case independently selected from CN, COOH, CONH2, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein Rx is C1-C4-alkyl, C1-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted by 1, 2, 3, 4 or 5 substituents Rx4 independently selected from C1-C4-alkyl, halogen, OH, CN, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy;wherein the acyclic moieties of R4 are unsubstituted or substituted with identical or different groups R4a which independently of one another are selected from:R4a halogen, OH, CN, COOH, CONH2, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy, C1-C6-alkylthio, aryl and phenoxy, wherein the aryl group is unsubstituted or carries 1, 2, 3, 4 or 5 substituents R41a selected from the group consisting of halogen, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy;wherein the carbocyclic, heteroaryl and aryl moieties of R4 are not further substituted or carry 1, 2, 3, 4, 5 or up to the maximum number of identical or different groups R4b which independently of one another are selected from:R4b halogen, OH, CN, COOH, CONH2, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-halogenalkoxy and C1-C6-alkylthio; andR5 is H.
  • 11. A composition, comprising one compound of formula I, as defined in claim 1, an N-oxide or an agriculturally acceptable salt thereof.
  • 12. A compound of formula I, as defined in claim 1, and of an agriculturally acceptable salt thereof for use in combating phytopathogenic fungi.
  • 13. A method for combating phytopathogenic fungi, comprising treating the fungi or the materials, plants, the soil or seeds to be protected against fungal attack with an effective amount of at least one compound of formula I, as defined in claim 1.
  • 14. A seed coated with at least one compound of the formula I, as defined in claim 1 or an agriculturally acceptable salt thereof, in an amount of from 0.1 to 10 kg per 100 kg of seed.
Priority Claims (1)
Number Date Country Kind
18155526.9 Feb 2018 EP regional
PCT Information
Filing Document Filing Date Country Kind
PCT/EP2019/052031 1/29/2019 WO 00