TREA

Imine substituted 2,4-diaryl-pyrroline derivatives as pesticides

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Information

  • Patent Grant
  • 8653000
  • Patent Number
    8,653,000
  • Date Filed
    Friday, September 30, 2011
    13 years ago
  • Date Issued
    Tuesday, February 18, 2014
    10 years ago
Information
Abstract
The present invention relates to imine compounds which are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. The invention also relates to a method for controlling invertebrate pests by using these compounds and to plant propagation material and to an agricultural and a veterinary composition comprising said compounds.
Description

The present invention relates to imine compounds which are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. The invention also relates to a method for controlling invertebrate pests by using these compounds and to plant propagation material and to an agricultural and a veterinary composition comprising said compounds.


Invertebrate pests and in particular arthropods and nematodes destroy growing and harvested crops and attack wooden dwelling and commercial structures, causing large economic loss to the food supply and to property. While a large number of pesticidal agents are known, due to the ability of target pests to develop resistance to said agents, there is an ongoing need for new agents for combating invertebrate pests, in particular insects, arachnids and nematodes.


WO 2010/072781 relates to isoxazoline compounds of formula




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wherein, inter alia, A1, A2, A3, A4, B1, B2 and B3 are independently carbon or nitrogen atoms. This document does not disclose imine compounds comprising the azolinyl or azolidinyl rings of the present invention.


It was an object of the present invention to provide compounds that have a good pesticidal activity, in particular insecticidal activity, and show a broad activity spectrum against a large number of different invertebrate pests, especially against difficult to control arthropod pests and/or nematodes.


It has been found that these objectives can be achieved by imine compounds of the formula I below, by their stereoisomers and by their salts, in particular their agriculturally or veterinarily acceptable salts.


Therefore, in a first aspect, the invention relates to imine compounds of formula I




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wherein

  • A1 is N or CH;
  • B1 is N or CH;
  • X is selected from the group consisting of C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-haloalkoxy-C1-C4-alkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl and C3-C6-halocycloalkyl;
  • Y is O, N—R3, S(O)n or a chemical bond;
  • R1 is selected from the group consisting of hydrogen; cyano; C1-C10-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; C1-C10-alkoxy; C1-C10-haloalkoxy; C1-C10-alkylthio; C1-C10-haloalkylthio; C1-C10-alkylsulfinyl; C1-C10-haloalkylsulfinyl; C1-C10-alkylsulfonyl; C1-C10-haloalkylsulfonyl; C3-C8-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; C2-C10-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; C2-C10-alkynyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; —C(═O)R6; —C(═O)OR7; —C(═O)N(R8)R9; —C(═S)R6; —C(═S)OR7; —C(═S)N(R8)R9; phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10; and a C-bound 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10;
  • R2 is selected from the group consisting of hydrogen; cyano; C1-C10-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; C3-C8-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; C2-C10-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; C2-C10-alkynyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; —N(R8)R9; —N(R8)C(═O)R6; —Si(R14)2R13; —OR7; —SR7; —S(O)mR7; —S(O)nN(R8)R9; —C(═O)R6; —C(═O)OR7; —C(═O)N(R8)R9; —C(═S)R6; —C(═S)OR7, —C(═S)N(R8)R9; —C(═NR8)R6; phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10;
    • with the proviso that R2 is not —OR7 if Y is O;
  • R3 is selected from the group consisting of hydrogen; cyano; C1-C10-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; C3-C8-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; C2-C10-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; C2-C10-alkynyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; —N(R8)R9; —Si(R14)2R13; —OR7; —SR7; —S(O)mR7; —S(O)nN(R8)R9; —C(═O)R6; —C(═O)OR7; —C(═O)N(R8)R9; —C(═S)R6; —C(═S)OR7; —C(═S)N(R8)R9; —C(═NR8)R6; phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10;
    • or R2 and R3 together form a group ═CR11R12; ═S(O)mR7; ═S(O)mN(R8)R9; ═NR8; or ═NOR7;
    • or R2 and R3 together form a C2-C7 alkylene chain, thus forming, together with the nitrogen atom to which they are bound, a 3-, 4-, 5-, 6-, 7- or 8-membered ring, where the alkylene chain may be interrupted by 1 or 2 O, S and/or NR18 and/or 1 or 2 of the CH2 groups of the alkylene chain may be replaced by a group C═O, C═S and/or C═NR18; and/or the alkylene chain may be substituted by one or more radicals selected from the group consisting of halogen, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10;
  • each R4 is independently selected from the group consisting of halogen; cyano; azido; nitro; —SCN; SF5; C1-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; C3-C8-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; C2-C6-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; C2-C6-alkynyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; —Si(R14)2R13; —OR7; —OS(O)nR7; —SR7; —S(O)mR7; —S(O)nN(R8)R9; —N(R8)R9; —N(R8)C(═O)R6; —C(═O)R6; —C(═O)OR7; —C(═NR8)H; —C(═NR8)R6; —C(═O)N(R8)R9; C(═S)N(R8)R9; phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10;
    • or two radicals R4 bound on adjacent carbon atoms may be together a group selected from —CH2CH2CH2CH2—, —CH═CH—CH═CH—, —N═CH—CH═CH—, —CH═N—CH═CH—, —N═CH—N═CH—, —OCH2CH2CH2—, —OCH═CHCH2—, —CH2OCH2CH2—, —OCH2CH2O—, —OCH2OCH2—, —CH2CH2CH2—, —CH═CHCH2—, —CH2CH2O—, —CH═CHO—, —CH2OCH2—, —CH2C(═O)O—, —C(═O)OCH2—, —O(CH2)O—, —SCH2CH2CH2—, —SCH═CHCH2—, —CH2SCH2CH2—, —SCH2CH2S—, —SCH2SCH2—, —CH2CH2S—, —CH═CHS—, —CH2SCH2—, —CH2C(═S)S—, —C(═S)SCH2—, —S(CH2)S—, —CH2CH2NR8—, —CH2CH═N—, —CH═CH—NR8—, —OCH═N— and —SCH═N—, thus forming, together with the carbon atoms to which they are bound, a 5- or 6-membered ring, where the hydrogen atoms of the above groups may be replaced by one or more substituents selected from halogen, methyl, halomethyl, hydroxyl, methoxy and halomethoxy or one or more CH2 groups of the above groups may be replaced by a C═O group;
  • each R5 is independently selected from the group consisting of halogen, cyano, azido, nitro, —SCN, SF5, C1-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6, C3-C8-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6, C2-C6-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6, C2-C6-alkynyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6, —Si(R14)2R13, —OR7, —OS(O)nR7, —SR7, —S(O)mR7, —S(O)nN(R8)R9, —N(R8)R9, N(R8)C(═O)R6, —C(═O)R6, —C(═O)OR7, —C(═S)R6, —C(═S)OR7, —C(═NR8)R6, —C(═O)N(R8)R9, —C(═S)N(R8)R9, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10;
  • each R6 is independently selected from the group consisting of cyano, azido, nitro, —SCN, SF5, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, —Si(R14)2R13, —OSO2R7, —SR7S(O)mR7, —S(O)nN(R8)R9, —N(R8)R9, —C(═O)N(R8)R9, —C(═S)N(R8)R9, —C(═O)OR7, —C(═O)R19, —C(═NR8)R19, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10;
    • and, in case R6 is bound to a cycloalkyl group, R6 may additionally be selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl and benzyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10;
    • and in groups —C(═O)R6, —C(═S)R6, —C(═NR8)R6 and —N(R8)C(═O)R6, R6 may additionally be selected from hydrogen, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl and benzyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10;
    • or two geminally bound radicals R6 together form a group selected from ═CR11R12, ═S(O)mR7, ═S(O)mN(R8)R9, ═NR8, ═NOR7 and ═NNR8;
    • or two radicals R6, together with the carbon atoms to which they are bound, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated carbocyclic or heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members;
  • each R7 is independently selected from the group consisting of hydrogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, —Si(R14)2R13, —SR8, —S(O)mR7, —S(O)nN(R8)R9, —N(R8)R9, —N═CR15R16, —C(═O)R17, —C(═O)N(R8)R9, —C(═S)N(R8)R9, —C(═O)OR17, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10;
    • with the proviso that R7 is not C1-C6-alkoxy or C1-C6-haloalkoxy if it is bound to an oxygen atom;
  • each R8 is independently selected from the group consisting of hydrogen, cyano, C1-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, where the alkyl moiety in the four last-mentioned radicals may be substituted by one or more radicals R19, C3-C8-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, C3-C8-cycloalkyl-C1-C4-alkyl where the cycloalkyl moiety may be partially or fully halogenated and/or may be substituted by one or more radicals R19, C2-C6-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, C2-C6-alkynyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, —S(O)mR20, —S(O)nN(R21)R22, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, benzyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10;
  • each R9 is independently selected from the group consisting of hydrogen, cyano, C1-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, where the alkyl moiety in the four last-mentioned radicals may be substituted by one or more radicals R19, C3-C8-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, C3-C8-cycloalkyl-C1-C4-alkyl where the cycloalkyl moiety may be partially or fully halogenated and/or may be substituted by one or more radicals R19, C2-C6-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, C2-C6-alkynyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, —S(O)mR20, —S(O)nN(R21)R22, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10;
    • or R8 and R9 together form a group ═CR11R12;
    • or R8 and R9, together with the nitrogen atom to which they are bound, may form a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring which may additionally containing 1 or 2 further heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10;
  • each R10 is independently selected from the group consisting of halogen, cyano, azido, nitro, —SCN, SF5, C1-C10-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, C3-C8-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, C2-C10-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, C2-C10-alkynyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, —Si(R14)2R13, —OR20, —OS(O)nR20, —R20, —S(O)mR20, —S(O)nN(R21)R22, —N(R21)R22, C(═O)R19, —C(═O)OR20, —C(═NR21)R22, —C(═O)N(R21)R22, —C(═S)N(R21)R22, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals independently selected from halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy; and a 3-, 4-, 5-, 6- or 7-membered saturated or unsaturated heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, which may be substituted by one or more radicals independently selected from halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy;
    • or two radicals R10 bound on adjacent atoms together form a group selected from —CH2CH2CH2CH2—, —CH═CH—CH═CH—, —N═CH—CH═CH—, —CH═N—CH═CH—, —N═CH—N═CH—, —OCH2CH2CH2—, —OCH═CHCH2—, —CH2OCH2CH2—, —OCH2CH2O—, —OCH2OCH2—, —CH2CH2CH2—, —CH═CHCH2—, —CH2CH2O—, —CH═CHO—, —CH2OCH2—, —CH2C(═O)O—, —C(═O)OCH2—, —O(CH2)O—, —SCH2CH2CH2—, —SCH═CHCH2—, —CH2SCH2CH2—, —SCH2CH2S—, —SCH2SCH2—, —CH2CH2S—, —CH═CHS—, —CH2SCH2—, —CH2C(═S)S—, —C(═S)SCH2—, —S(CH2)S—, —CH2CH2NR21—, —CH2CH═N—, —CH═CH—NR21—, —OCH═N— and —SCH═N—, thus forming, together with the atoms to which they are bound, a 5- or 6-membered ring, where the hydrogen atoms of the above groups may be replaced by one or more substituents selected from halogen, methyl, halomethyl, hydroxyl, methoxy and halomethoxy or one or more CH2 groups of the above groups may be replaced by a C═O group;
  • R11, R12 are, independently of each other and independently of each occurrence, selected from the group consisting of hydrogen, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-haloalkoxy-C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, —C(═O)R19, —C(═O)OR20, —C(═NR21)R22, —C(═O)N(R21)R22, —C(═S)N(R21)R22, phenyl which may be substituted by 1, 2, 3, 4, or 5 radicals R10; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, which may be substituted by one or more radicals R10;
  • R13, R14 are, independently of each other and independently of each occurrence, selected from the group consisting of C1-C4-alkyl, C3-C6-cycloalkyl, C1-C4-alkoxy-C1-C4-alkyl, phenyl and benzyl;
  • R15, R16 are, independently of each other and independently of each occurrence, selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-haloalkoxy-C1-C6-alkyl, phenyl which may be substituted by 1, 2, 3, 4, or 5 radicals R10; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, which may be substituted by one or more radicals R10;
  • each R17 is independently selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-haloalkoxy-C1-C6-alkyl, phenyl and benzyl;
  • each R18 is independently defined like R3;
  • each R19 is independently selected from the group consisting of cyano, azido, nitro, —SCN, SF5, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, —Si(R14)2R13, —OR20, —OSO2R20, —SR20, —S(O)mR20, —S(O)nN(R21)R22, —N(R21)R22, —C(═O)N(R21)R22, —C(═S)N(R21)R22, —C(═O)OR20, —C(═O)R20, —C(═NR21)R20, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals independently selected from halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals independently selected from halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy;
    • and, in case R19 is bound to a cycloalkyl group, R19 may additionally be selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl; and in groups —C(═O)R19, R19 may additionally be selected from hydrogen, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, and C2-C6-haloalkynyl;
    • or two geminally bound radicals R19 together form a group selected from ═CR11R12, ═S(O)mR20, ═S(O)mN(R21)R22, ═NR21, ═NOR20 and ═NNR21;
    • or two radicals R19, together with the carbon atoms to which they are bound, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated carbocyclic or heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members;
  • each R20 is independently selected from the group consisting of hydrogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, —Si(R14)2R13, C1-C6-alkylaminosulfonyl, amino, C1-C6-alkylamino, di-(C1-C6-alkyl)-amino, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, aminocarbonyl, C1-C6-alkylaminocarbonyl, di-(C1-C6-alkyl)-aminocarbonyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals independently selected from halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy, benzyl which may be substituted by 1, 2, 3, 4 or 5 radicals independently selected from halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals independently selected from halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy;
    • with the proviso that R20 is not C1-C6-alkoxy or C1-C6-haloalkoxy if it is bound to an oxygen atom;
  • R21 and R22 are independently of each other and independently of each occurence selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals independently selected from halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy, benzyl which may be substituted by 1, 2, 3, 4 or 5 radicals independently selected from halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals independently selected from halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy;
    • or R21 and R22, together with the nitrogen atom to which they are bound, may form a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring which may additionally containing 1 or 2 further heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals selected from halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy;
  • each m is independently 1 or 2;
  • each n is independently 0, 1 or 2;
  • p is 0, 1, 2, 3 or 4; and
  • q is 0, 1, 2, 3, 4 or 5;


    and the stereoisomers and agriculturally or veterinarily acceptable salts thereof.


The present invention also provides an agricultural composition comprising at least one compound of the formula I as defined herein and/or an agriculturally acceptable salt thereof and at least one liquid or solid carrier.


The present invention also provides a veterinary composition comprising at least one compound of the formula I as defined herein and/or a veterinarily acceptable salt thereof and at least one liquid or solid carrier.


The present invention also provides a method for controlling invertebrate pests which method comprises treating the pests, their food supply, their habitat or their breeding ground or a cultivated plant, plant propagation materials (such as seed), soil, area, material or environment in which the pests are growing or may grow, or the materials, cultivated plants, plant propagation materials (such as seed), soils, surfaces or spaces to be protected from pest attack or infestation with a pesticidally effective amount of a compound of formula I or a salt thereof as defined herein.


The present invention also relates to plant propagation material, in particular seed, comprising at least one compound of formula I and/or an agriculturally acceptable salt thereof as defined herein.


The present invention further relates to a method for treating or protecting an animal from infestation or infection by parasites which comprises bringing the animal in contact with a parasiticidally effective amount of a compound of the formula I or a veterinarily acceptable salt thereof as defined herein. Bringing the animal in contact with the compound I, its salt or the veterinary composition of the invention means applying or administering it to the animal.


The term “steroisomers” encompasses both optical isomers, such as enantiomers or diastereomers, the latter existing due to more than one center of chirality in the molecule, as well as geometrical isomers (cis/trans isomers).


Depending on the substitution pattern, the compounds of the formula I may have one or more centers of chirality, in which case they are present as mixtures of enantiomers or diastereomers. One center of chirality is the carbon ring atom of the pyrroline ring carrying radical X. The invention provides both the pure enantiomers or diastereomers and their mixtures and the use according to the invention of the pure enantiomers or diastereomers of the compound I or its mixtures. Enantiomers with respect to the position of the group X and the ring containing B1 as ring member on the pyrroline ring may be represented by following formulae I-A and I-B




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Among these, preference is given to enantiomer I-A, especially if X is CF3. Thus, a preferred embodiment of the invention relates to compounds of formula I-A




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wherein the variables have one of the above-given general, or in particular one of the below-given preferred meanings. Preferably, X in compounds I-A is CF3.


Suitable compounds of the formula I also include all possible geometrical stereoisomers (cis/trans isomers) and mixtures thereof. Cis/trans isomers may be present with respect to the imine group. Preference is given to compounds wherein the group —Y—R2 is trans with respect to the ring containing A1 as ring member, i.e. to compounds of formula trans-I




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The compounds of the present invention may be amorphous or may exist in one or more different crystalline states (polymorphs) which may have a different macroscopic properties such as stability or show different biological properties such as activities.


The present invention includes both amorphous and crystalline compounds of the formula I, mixtures of different crystalline states of the respective compound I, as well as amorphous or crystalline salts thereof.


Salts of the compounds of the formula I are preferably agriculturally and veterinarily acceptable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid of the anion in question if the compound of formula I has a basic functionality or by reacting an acidic compound of formula I with a suitable base.


Suitable agriculturally acceptable salts are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not have any adverse effect on the action of the compounds according to the present invention.


Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium (NH4+) and substituted ammonium in which one to four of the hydrogen atoms are replaced by C1-C4-alkyl, C1-C4-hydroxyalkyl, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkyl, hydroxy-C1-C4-alkoxy-C1-C4-alkyl, phenyl or benzyl. Examples of substituted ammonium ions comprise methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2-hydroxyethoxy)ethylammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzl-triethylammonium, 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, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C1-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting a compound of formulae I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.


By the term “veterinarily acceptable salts” is meant salts of those cations or anions which are known and accepted in the art for the formation of salts for veterinary use. Suitable acid addition salts, e.g. formed by compounds of formula I containing a basic nitrogen atom, e.g. an amino group, include salts with inorganic acids, for example hydrochlorids, sulphates, phosphates, and nitrates and salts of organic acids for example acetic acid, maleic acid, dimaleic acid, fumaric acid, difumaric acid, methane sulfenic acid, methane sulfonic acid, and succinic acid.


The term “invertebrate pest” as used herein encompasses animal populations, such as insects, arachnids and nematodes, which may attack plants, thereby causing substantial damage to the plants attacked, as well as ectoparasites which may infest animals, in particular warm blooded animals such as e.g. mammals or birds, or other higher animals such as reptiles, amphibians or fish, thereby causing substantial damage to the animals infested.


The term “plant propagation material” as used herein includes all the generative parts of the plant such as seeds and vegetative plant material 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. Seedlings and young plants, which are to be transplanted after germination or after emergence from soil, may also be included. These plant propagation materials may be treated prophylactically with a plant protection compound either at or before planting or transplanting.


The term “plants” comprises any types of plants including “non-cultivated plants” and in particular “cultivated plants”.


The term “non-cultivated plants” refers to any wild type species or related species or related genera of a cultivated plant.


The term “cultivated plants” as used herein includes plants which have been modified by breeding, mutagenesis or genetic engineering. Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant. Such genetic modifications also include but are not limited to targeted post-transtional modification of protein(s) (oligo- or polypeptides) poly for example by glycosylation or polymer additions such as prenylated, acetylated or farnesylated moieties or PEG moieties (e.g. as disclosed in Biotechnol Prog. 2001 July-August; 17(4):720-8, Protein Eng Des Sel. 2004 January; 17(1):57-66, Nat. Protoc. 2007; 2(5):1225-35, Curr. Opin. Chem. Biol. 2006 October; 10(5):487-91. Epub 2006 August 28, Biomaterials. 2001 March; 22(5):405-17, Bioconjug Chem. 2005 January-February; 16(1):113-21).


The term “cultivated plants” as used herein further includes plants that have been rendered tolerant to applications of specific classes of herbicides, such as hydroxy-phenylpyruvate dioxygenase (HPPD) inhibitors; acetolactate synthase (ALS) inhibitors, such as sulfonyl ureas (see e.g. U.S. Pat. No. 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073) or imidazolinones (see e.g. U.S. Pat. No. 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073); enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors, such as glyphosate (see e.g. WO 92/00377); glutamine synthetase (GS) inhibitors, such as glufosinate (see e.g. EP-A-0242236, EP-A-242246) or oxynil herbicides (see e.g. U.S. Pat. No. 5,559,024) as a result of conventional methods of breeding or genetic engineering. Several cultivated plants have been rendered tolerant to herbicides by conventional methods of breeding (mutagenesis), for example Clearfield® summer rape (Canola) being tolerant to imidazolinones, e.g. imazamox. Genetic engineering methods have been used to render cultivated plants, such as soybean, cotton, corn, beets and rape, tolerant to herbicides, such as glyphosate and glufosinate, some of which are commercially available under the trade names RoundupReady® (glyphosate) and LibertyLink® (glufosinate).


The term “cultivated plants” as used herein further includes plants that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus bacillus, particularly from bacillus thuringiensis, such as ä-endotoxins, e.g. CryIA(b), CryIA(c), CryIF, CryIF(a2), CryIIA(b), CryIIIA, CryIIIB(b1) or Cry9c; vegetative insecticidal proteins (VIP), e.g. VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, for example Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins; toxins produced by fungi, such Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as blockers of sodium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilben synthase, bibenzyl synthase, chitinases or glucanases. In the context of the present invention these insecticidal proteins or toxins are to be understood expressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a new combination of protein domains, (see, for example WO 02/015701). Further examples of such toxins or genetically-modified plants capable of synthesizing such toxins are dis-closed, for example, in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/018810 und WO 03/052073. The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above. These insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins protection from harmful pests from certain taxonomic groups of arthropods insects, particularly to beetles (Coleoptera), flies (Diptera), and butterflies and moths (Lepidoptera) and to plant parasitic nematodes (Nematoda).


The term “cultivated plants” as used herein further includes plants that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens. Examples of such proteins are the so-called “pathogenesis-related proteins” (PR proteins, see, for example EP-A 0 392 225), plant disease resistance genes (for example potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the mexican wild potato Solanum bulbocastanum) or T4-lyso-zym (e.g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora). The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.


The term “cultivated plants” as used herein further includes plants that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e.g. bio mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environ-mental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.


The term “cultivated plants” as used herein further includes plants that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve human or animal nutrition, for ex-ample oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e.g. Nexera® rape).


The term “cultivated plants” as used herein further includes plants that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve raw material production, for example potatoes that produce increased amounts of amylopectin (e.g. Amflora® potato).


The organic moieties mentioned in the above definitions of the variables are—like the term halogen—collective terms for individual listings of the individual group members. The prefix Cn-Cm indicates in each case the possible number of carbon atoms in the group.


The term halogen denotes in each case fluorine, bromine, chlorine or iodine, in particular fluorine, chlorine or bromine.


The term “C1-C10-alkyl” as used herein and in the alkyl moieties of alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl and the like refers to saturated straight-chain or branched hydrocarbon radicals having 1 to 2 (“C1-C2-alkyl”), 1 to 4 (“C1-C4-alkyl”), 1 to 6 (“C1-C6-alkyl”), 1 to 8 (“C1-C8-alkyl”) or 1 to 10 (“C1-C10-alkyl”) carbon atoms. C1-C2-Alkyl is methyl or ethyl. C1-C4-Alkyl is additionally propyl, isopropyl, butyl, 1-methylpropyl(sec-butyl), 2-methylpropyl(isobutyl) or 1,1-dimethylethyl(tert-butyl). C1-C6-Alkyl is additionally also, for example, 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, or 1-ethyl-2-methylpropyl. C1-C8-Alkyl is additionally also, for example, heptyl, octyl, 2-ethylhexyl and positional isomers thereof. C1-C10-Alkyl is additionally also, for example, nonyl, decyl and positional isomers thereof.


The term “C1-C10-haloalkyl” as used herein, which is also expressed as “C1-C10-alkyl which is partially or fully halogenated”, refers to straight-chain or branched alkyl groups having 1 to 2 (“C1-C2-haloalkyl”), 1 to 4 (“C1-C4-haloalkyl”), 1 to 6 (“C1-C6-haloalkyl”), 1 to 8 (“C1-C8-haloalkyl”) or 1 to 10 (“C1-C10-haloalkyl”) carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above: in particular C1-C2-haloalkyl, 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, pentafluoroethyl or 1,1,1-trifluoroprop-2-yl.


“Halomethyl” is methyl in which 1, 2 or 3 of the hydrogen atoms are replaced by halogen atoms. Examples are bromomethyl, chloromethyl, fluoromethyl, dichloromethyl, trichloromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl and the like.


The term “C2-C10-alkenyl” as used herein and in the alkenyl moiety of alkenyloxy and the like refers to monounsaturated straight-chain or branched hydrocarbon radicals having 2 to 4 (“C2-C4-alkenyl”), 2 to 6 (“C2-C6-alkenyl”), 2 to 8 (“C2-C8-alkenyl”), 3 to 8 (“C3-C8-alkenyl”), 2 to 10 (“C2-C10-alkenyl”) or 3 to 10 (“C3-C10-alkenyl”) carbon atoms and a double bond in any position, for example C2-C4-alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl or 2-methyl-2-propenyl; C2-C6-alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl, 1-ethyl-2-methyl-2-propenyl and the like, or C2-C10-alkenyl, such as the radicals mentioned for C2-C6-alkenyl and additionally 1-heptenyl, 2-heptenyl, 3-heptenyl, 1-octenyl, 2-octenyl, 3-octenyl, 4-octenyl, 1-nonenyl, 2-nonenyl, 3-nonenyl, 4-nonenyl, 1-decenyl, 2-decenyl, 3-decenyl, 4-decenyl, 5-decenyl and the positional isomers thereof.


The term “C2-C10-haloalkenyl” as used herein, which is also expressed as “C1-C10-alkenyl which is partially or fully halogenated”, and the haloalkenyl moieties in haloalkenyloxy, haloalkenylcarbonyl and the like refers to unsaturated straight-chain or branched hydrocarbon radicals having 2 to 4 (“C2-C4-haloalkenyl”), 2 to 6 (“C2-C6-haloalkenyl”), 2 to 8 (“C2-C6-haloalkenyl”) or 2 to 10 (“C2-C10-haloalkenyl”) carbon atoms and a double bond in any position (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine, for example chlorovinyl, chloroallyl and the like.


The term “C2-C10-alkynyl” as used herein and the alkynyl moieties in alkynyloxy, alkynylcarbonyl and the like refers to straight-chain or branched hydrocarbon groups having 2 to 4 (“C2-C4-alkynyl”), 2 to 6 (“C2-C6-alkynyl”), 2 to 8 (“C2-C8-alkynyl”), 3 to 8 (“C3-C8-alkynyl”), 2 to 10 (“C2-C10-alkynyl”) or 3 to 10 (“C3-C8-alkynyl”) carbon atoms and one or two triple bonds in any position, for example C2-C4-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl and the like, C2-C6-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl and the like;


The term “C2-C10-haloalkynyl” as used herein, which is also expressed as “C1-C10-alkynyl which is partially or fully halogenated”, and the haloalkynyl moieties in haloalkynyloxy, haloalkynylcarbonyl and the like refers to unsaturated straight-chain or branched hydrocarbon radicals having 2 to 4 (“C2-C4-haloalkynyl”), 3 to 4 (“C3-C4-haloalkynyl”), 2 to 6 (“C2-C6-haloalkynyl”), 3 to 6 (“C3-C6-haloalkynyl”), 2 to 8 (“C2-C8-haloalkynyl”), 3 to 8 (“C3-C8-haloalkynyl”), 2 to 10 (“C2-C10-haloalkynyl”) or 3 to 10 (“C3-C10-haloalkynyl”) carbon atoms and one or two triple bonds in any position (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine;


The term “C3-C8-cycloalkyl” as used herein refers to mono- or bi- or polycyclic saturated hydrocarbon radicals having 3 to 8, in particular 3 to 6 carbon atoms (“C3-C6-cycloalkyl”). Examples of monocyclic radicals having 3 to 6 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Examples of monocyclic radicals having 3 to 8 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl. Examples of bicyclic radicals having 7 or 8 carbon atoms comprise bicyclo[2.2.1]heptyl, bicyclo[3.1.1]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1]octyl.


The term “C3-C8-halocycloalkyl” as used herein, which is also expressed as “C3-C8-cycloalkyl which is partially or fully halogenated”, and the halocycloalkyl moieties in halocycloalkoxy, halocycloalkylcarbonyl and the like refers to mono- or bi- or polycyclic saturated hydrocarbon groups having 3 to 8 (“C3-C8-halocycloalkyl”) or preferably 3 to 6 (“C3-C6-halocycloalkyl”) carbon ring members (as mentioned above) in which some or all of the hydrogen atoms are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine.


The term “C3-C8-cycloalkyl-C1-C4-alkyl” refers to a C3-C8-cycloalkyl group as defined above which is bound to the remainder of the molecule via a C1-C4-alkyl group, as defined above. Examples are cyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl, cyclobutylpropyl, cyclopentylmethyl, cycloppentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl, cyclohexylpropyl, and the like.


The term “C1-C2-alkoxy” is a C1-C2-alkyl group, as defined above, attached via an oxygen atom. The term “C1-C4-alkoxy” is a C1-C4-alkyl group, as defined above, attached via an oxygen atom. The term “C1-C6-alkoxy” is a C1-C6-alkyl group, as defined above, attached via an oxygen atom. The term “C1-C10-alkoxy” is a C1-C10-alkyl group, as defined above, attached via an oxygen atom. C1-C2-Alkoxy is methoxy or ethoxy. C1-C4-Alkoxy is additionally, for example, n-propoxy, 1-methylethoxy(isopropoxy), butoxy, 1-methylpropoxy(sec-butoxy), 2-methylpropoxy(isobutoxy) or 1,1-dimethylethoxy(tertbutoxy). C1-C6-Alkoxy is additionally, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy. C1-C8-Alkoxy is additionally, for example, heptyloxy, octyloxy, 2-ethylhexyloxy and positional isomers thereof. C1-C10-Alkoxy is additionally, for example, nonyloxy, decyloxy and positional isomers thereof.


The term “C1-C2-haloalkoxy” is a C1-C2-haloalkyl group, as defined above, attached via an oxygen atom. The term “C1-C4-haloalkoxy” is a C1-C4-haloalkyl group, as defined above, attached via an oxygen atom. The term “C1-C6-haloalkoxy” is a C1-C6-haloalkyl group, as defined above, attached via an oxygen atom. The term “C1-C10-haloalkoxy” is a C1-C10-haloalkyl group, as defined above, attached via an oxygen atom. C1-C2-Haloalkoxy is, for example, OCH2F, OCHF2, OCF3, OCH2Cl, OCHCl2, OCCl3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 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 or OC2F5. C1-C4-Haloalkoxy is additionally, for example, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2—C2F5, OCF2—C2F5, 1-(CH2F)-2-fluoroethoxy, 1-(CH2Cl)-2-chloroethoxy, 1-(CH2Br)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy. C1-C6-Haloalkoxy is additionally, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-brompentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy.


The term “C1-C2-alkylthio” is a C1-C2-alkyl group, as defined above, attached via a sulfur atom. The term “C1-C4-alkylthio” is a C1-C4-alkyl group, as defined above, attached via a sulfur atom. The term “C1-C6-alkylthio” is a C1-C6-alkyl group, as defined above, attached via a sulfur atom. The term “C1-C10-alkylthio” is a C1-C10-alkyl group, as defined above, attached via a sulfur atom. C1-C2-Alkylthio is methylthio or ethylthio. C1-C4-Alkylthio is additionally, for example, n-propylthio, 1-methylethylthio(isopropylthio), butylthio, 1-methylpropylthio(sec-butylthio), 2-methylpropylthio(isobutylthio) or 1,1-dimethylethylthio(tert-butylthio). C1-C6-Alkylthio is additionally, for example, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio or 1-ethyl-2-methylpropylthio. C1-C8-Alkylthio is additionally, for example, heptylthio, octylthio, 2-ethylhexylthio and positional isomers thereof. C1-C10-Alkylthio is additionally, for example, nonylthio, decylthio and positional isomers thereof.


The term “C1-C2-haloalkylthio” is a C1-C2-haloalkyl group, as defined above, attached via a sulfur atom. The term “C1-C4-haloalkylthio” is a C1-C4-haloalkyl group, as defined above, attached via a sulfur atom. The term “C1-C6-haloalkylthio” is a C1-C6-haloalkyl group, as defined above, attached via a sulfur atom. The term “C1-C10-haloalkylthio” is a C1-C10-haloalkyl group, as defined above, attached via a sulfur atom. C1-C2-Haloalkylthio is, for example, SCH2F, SCHF2, SCF3, SCH2Cl, SCHC2, SCC3, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio or SC2F5. C1-C4-Haloalkylthio is additionally, for example, 2-fluoropropylthio, 3-fluoropropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2,3-dichloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio, SCH2—C2F5, SCF2—C2F5, 1-(CH2F)-2-fluoroethylthio, 1-(CH2Cl)-2-chloroethylthio, 1-(CH2Br)-2-bromoethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio or nonafluorobutylthio. C1-C6-Haloalkylthio is additionally, for example, 5-fluoropentylthio, 5-chloropentylthio, 5-brompentylthio, 5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio, 6-chlorohexylthio, 6-bromohexylthio, 6-iodohexylthio or dodecafluorohexylthio.


The term “C1-C2-alkylsulfinyl” is a C1-C2-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term “C1-C4-alkylsulfinyl” is a C1-C4-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term “C1-C6-alkylsulfinyl” is a C1-C6-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term “C1-C10-alkylsulfinyl” is a C1-C10-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. C1-C2-Alkylsulfinyl is methylsulfinyl or ethylsulfinyl. C1-C4-Alkylsulfinyl is additionally, for example, n-propylsulfinyl, 1-methylethylsulfinyl(isopropylsulfinyl), butylsulfinyl, 1-methylpropylsulfinyl(sec-butylsulfinyl), 2-methylpropylsulfinyl(isobutylsulfinyl) or 1,1-dimethylethylsulfinyl(tert-butylsulfinyl). C1-C6-Alkylsulfinyl is additionally, for example, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsuIfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl. C1-C8-Alkylsulfinyl is additionally, for example, heptylsulfinyl, octylsulfinyl, 2-ethylhexylsulfinyl and positional isomers thereof. C1-C10-Alkylsulfinyl is additionally, for example, nonylsulfinyl, decylsulfinyl and positional isomers thereof.


The term “C1-C2-haloalkylsulfinyl” is a C1-C2-haloalkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term “C1-C4-haloalkylsulfinyl” is a C1-C4-haloalkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term “C1-C6-haloalkylsulfinyl” is a C1-C6-haloalkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term “C1-C10-haloalkylsulfinyl” is a C1-C10-haloalkyl group, as defined above, attached via a sulfinyl [S(O)] group. C1-C2-Haloalkylsulfinyl is, for example, S(O)CH2F, S(O)CHF2, S(O)CF3, S(O)CH2Cl, S(O)CHCl2, S(O)CCl3, chlorofluoromethylsulfinyl, dichlorofluoromethylsulfinyl, chlorodifluoromethylsulfinyl, 2-fluoroethylsulfinyl, 2-chloroethylsulfinyl, 2-bromoethylsulfinyl, 2-iodoethylsulfinyl, 2,2-difluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 2-chloro-2-fluoroethylsulfinyl, 2-chloro-2,2-difluoroethylsulfinyl, 2,2-dichloro-2-fluoroethylsulfinyl, 2,2,2-trichloroethylsulfinyl or S(O)C2F5. C1-C4-Haloalkylsulfinyl is additionally, for example, 2-fluoropropylsulfinyl, 3-fluoropropylsulfinyl, 2,2-difluoropropylsulfinyl, 2,3-difluoropropylsulfinyl, 2-chloropropylsulfinyl, 3-chloropropylsulfinyl, 2,3-dichloropropylsulfinyl, 2-bromopropylsulfinyl, 3-bromopropylsulfinyl, 3,3,3-trifluoropropylsulfinyl, 3,3,3-trichloropropylsulfinyl, S(O)CH2—C2F5, S(O)CF2—C2F5, 1-(CH2F)-2-fluoroethylsulfinyl, 1-(CH2Cl)-2-chloroethylsulfinyl, 1-(CH2Br)-2-bromoethylsulfinyl, 4-fluorobutylsulfinyl, 4-chlorobutylsulfinyl, 4-bromobutylsulfinyl or nonafluorobutylsulfinyl. C1-C6-Haloalkylsulfinyl is additionally, for example, 5-fluoropentylsulfinyl, 5-chloropentylsulfinyl, 5-brompentylsulfinyl, 5-iodopentylsulfinyl, undecafluoropentylsulfinyl, 6-fluorohexylsulfinyl, 6-chlorohexylsulfinyl, 6-bromohexylsulfinyl, 6-iodohexylsulfinyl or dodecafluorohexylsulfinyl.


The term “C1-C2-alkylsulfonyl” is a C1-C2-alkyl group, as defined above, attached via a sulfonyl[S(O)2] group. The term “C1-C4-alkylsulfonyl” is a C1-C4-alkyl group, as defined above, attached via a sulfonyl[S(O)2] group. The term “C1-C6-alkylsulfonyl” is a C1-C6-alkyl group, as defined above, attached via a sulfonyl[S(O)2] group. The term “C1-C10-alkylsulfonyl” is a C1-C10-alkyl group, as defined above, attached via a sulfonyl[S(O)2]group. C1-C2-Alkylsulfonyl is methylsulfonyl or ethylsulfonyl. C1-C4-Alkylsulfonyl is additionally, for example, n-propylsulfonyl, 1-methylethylsulfonyl(isopropylsulfonyl), butylsulfonyl, 1-methylpropylsulfonyl(sec-butylsulfonyl), 2-methylpropylsulfonyl(isobutylsulfonyl) or 1,1-dimethylethylsulfonyl(tert-butylsulfonyl). C1-C6-Alkylsulfonyl is additionally, for example, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl or 1-ethyl-2-methylpropylsulfonyl. C1-C8-Alkylsulfonyl is additionally, for example, heptylsulfonyl, octylsulfonyl, 2-ethylhexylsulfonyl and positional isomers thereof. C1-C10-Alkylsulfonyl is additionally, for example, nonylsulfonyl, decylsulfonyl and positional isomers thereof.


The term “C1-C2-haloalkylsulfonyl” is a C1-C2-haloalkyl group, as defined above, attached via a sulfonyl[S(O)2] group. The term “C1-C4-haloalkylsulfonyl” is a C1-C4-haloalkyl group, as defined above, attached via a sulfonyl [S(O)2] group. The term “C1-C6-haloalkylsulfonyl” is a C1-C6-haloalkyl group, as defined above, attached via a sulfonyl [S(O)2] group. The term “C1-C10-haloalkylsulfonyl” is a C1-C10-haloalkyl group, as defined above, attached via a sulfonyl[S(O)2] group. C1-C2-Haloalkylsulfonyl is, for example, S(O)2CH2F, S(O)2CHF2, S(O)2CF3, S(O)2CH2Cl, S(O)2CHCl2, S(O)2CCO3, chlorofluoromethylsulfonyl, dichlorofluoromethylsulfonyl, chlorodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2,2-difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl or S(O)2C2F5. C1-C4-Haloalkylsulfonyl is additionally, for example, 2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl, 2-chloropropylsulfonyl, 3-chloropropylsulfonyl, 2,3-dichloropropylsulfonyl, 2-bromopropylsulfonyl, 3-bromopropylsulfonyl, 3,3,3-trifluoropropylsulfonyl, 3,3,3-trichloropropylsulfonyl, S(O)2CH2—C2F5, S(O)2CF2—C2F5, 1-(CH2F)-2-fluoroethylsulfonyl, 1-(CH2Cl)-2-chloroethylsulfonyl, 1-(CH2Br)-2-bromoethylsulfonyl, 4-fluorobutylsulfonyl, 4-chlorobutylsulfonyl, 4-bromobutylsulfonyl or nonafluorobutylsulfonyl. C1-C6-Haloalkylsulfonyl is additionally, for example, 5-fluoropentylsulfonyl, 5-chloropentylsulfonyl, 5-brompentylsulfonyl, 5-iodopentylsulfonyl, undecafluoropentylsulfonyl, 6-fluorohexylsulfonyl, 6-chlorohexylsulfonyl, 6-bromohexylsulfonyl, 6-iodohexylsulfonyl or dodecafluorohexylsulfonyl.


The term “3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members” as used herein refers to monocyclic radicals, the monocyclic radicals being saturated, partially unsaturated or aromatic. The heterocyclic radical may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member.


Examples of 3-, 4-, 5-, 6- or 7-membered saturated heterocyclyl include:


Oxiranyl, aziridinyl, oxetidinyl (radical of trimethylene oxide), thietidinyl (radical of trimethylene sulfide), azetidinyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 1,3-dioxolane-2-yl, 1,3-dioxolane-4-yl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 1,3-thiolane-2-yl, 1,3-dithiolane-4-yl, 1-thia-3-oxolan-2-yl, 1-thia-3-oxolan-4-yl, 1-thia-3-oxolan-5-yl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 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-tetrahydropyranyl, 3-tetrahydropyranyl, 4-tetrahydropyranyl, 1,3-dioxan-2-yl, 1,3-dioxan-4-yl, 1,3-dioxan-5-yl, 1,4-dioxan-2-yl, 2-thianyl, 3-thianyl, 4-thianyl, 1,3-dithian-2-yl, 1,3-dithian-4-yl, 1,3-dithian-5-yl, 1,4-dithian-2-yl, 1-oxa-3-thian-2-yl, 1-oxa-3-thian-4-yl, 1-oxa-3-thian-5-yl, 1-oxa-3-thian-6-yl, 1-oxa-4-thian-2-yl, 1-oxa-4-thian-3-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 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, 2-morpholinyl, 3-morpholinyl, 2-thiomorpholinyl, 3-thiomorpholinyl, 1-oxothiomorpholin-2-yl, 1-oxothiomorpholin-3-yl, 1,1-dioxothiomorpholin-2-yl, 1,1-dioxothiomorpholin-3-yl, hexahydroazepin-1-, -2-, -3- or -4-yl, hexahydrooxepinyl, hexahydro-1,3-diazepinyl, hexahydro-1,4-diazepinyl, hexahydro-1,3-oxazepinyl, hexahydro-1,4-oxazepinyl, hexahydro-1,3-dioxepinyl, hexahydro-1,4-dioxepinyl and the like.


Examples of 3-, 4-, 5-, 6- or 7-membered partially unsaturated heterocyclyl include: 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-, 3-, 4-, 5- or 6-di- or tetrahydropyridinyl, 3-di- or tetrahydropyridazinyl, 4-di- or tetrahydropyridazinyl, 2-di- or tetrahydropyrimidinyl, 4-di- or tetrahydropyrimidinyl, 5-di- or tetrahydropyrimidinyl, di- or tetrahydropyrazinyl, 1,3,5-di- or tetrahydrotriazin-2-yl, 1,2,4-di- or tetrahydrotriazin-3-yl, 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, tetrahydrooxepinyl, 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, tetrahydro-1,3-diazepinyl, tetrahydro-1,4-diazepinyl, tetrahydro-1,3-oxazepinyl, tetrahydro-1,4-oxazepinyl, tetrahydro-1,3-dioxepinyl and tetrahydro-1,4-dioxepinyl.


3-, 4-, 5-, 6- or 7-membered aromatic heterocyclyl is 5- or 6-membered aromatic heterocyclyl(hetaryl). Examples are: 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,3,4-triazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl.


C2-C7-alkylene is divalent branched or preferably unbranched saturated aliphatic chain having 2 to 7 carbon atoms, for example CH2CH2, —CH(CH3)—, CH2CH2CH2, CH(CH3)CH2, CH2CH(CH3), CH2CH2CH2CH2, CH2CH2CH2CH2CH2, CH2CH2CH2CH2CH2CH2, and CH2CH2CH2CH2CH2CH2CH2


The remarks made below concerning preferred embodiments of the variables of the compounds of formula I, especially with respect to their substituents X, Y, A1, B1, R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21, R22, m, n, p and q, the features of the use and method according to the invention and of the composition of the invention are valid both on their own and, in particular, in every possible combination with each other.


As a matter of course, the q radicals R5 replace a hydrogen atom on a carbon ring atom. For instance, if B1 is defined to be CH and if this position is to be substituted by a radical R5, then B1 is of course C—R5. If there is more than one radical R5, these can be the same or different.


As a matter of course, the p radicals R4 replace a hydrogen atom on a carbon ring atom. For instance, if A1 is defined to be CH and if this position is to be substituted by a radical R4, then A1 is of course C—R4. If there is more than one radical R4, these can be the same or different.


Preferably, A1 is CH.


In a preferred embodiment, the ring comprising the group A1 as ring member carries 0, 1 or 2, preferably 0 or 1 and in particular 1 substituent R4. In other words, p is preferably 0, 1 or 2, more preferably 0 or 1 and in particular 1. In case A1 is CH and p is 1, the substituent R4 is preferably bound on the position of A1. In other words, A1 is in this case preferably C—R4.


In case p is 2, two substituents R4 bound on adjacent carbon atoms preferably form together a group selected from —CH2CH2CH2CH2— and —CH═CH—CH═CH— and more preferably —CH═CH—CH═CH—, thus yielding a fused phenyl ring.


Preferably, B1 is CH.


q is preferably 0, 1, 2 or 3, more preferably 1, 2 or 3, even more preferably 2 or 3 and in particular 2. If q is 3 and B1 is CH, then the three substituents R5 are preferably bound in the positions 3, 4 and 5 (relative to the 1-position of the attachment point of this ring to the remainder of the molecule), B1 thus being C—R5. If q is 2 and B1 is CH, then the two substituents R5 are preferably bound in the positions 3 and 5, B1 thus being C—R5.


X is preferably selected from the group consisting of C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-haloalkoxy-C1-C4-alkyl, C3-C6-cycloalkyl and C3-C6-halocycloalkyl. More preferably, X is selected from the group consisting of C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl and C3-C6-halocycloalkyl. Even more preferably, X is selected from the group consisting of C1-C4-alkyl and C1-C4-haloalkyl. In particular, X is C1-C4-haloalkyl, specifically C1-C2-haloalkyl and more specifically halomethyl, in particular fluoromethyl, such as fluoromethyl, difluoromethyl and trifluoromethyl, or fluorochloromethyl, such as chlorodifluoromethyl or dichlorofluoromethyl. Specifically, X is selected from CF3, CHF2 and CF2Cl and is very specifically trifluoromethyl.


Y is preferably a chemical bond, O or NR3. R3 has one of the meanings given above or preferably one of the preferred meanings given below. More preferably, Y is O or NR3. In particular, Y is NR3.


Preferably, R1 is selected from the group consisting of hydrogen; cyano; C1-C10-alkyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; C1-C10-alkoxy; C1-C10-haloalkoxy; C3-C8-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; C2-C10-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; C2-C10-alkynyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; —C(═O)R6; —C(═O)OR7; —C(═O)N(R8)R9; —C(═S)R6; —C(═S)OR7; —C(═S)N(R8)R9; phenyl which may be substituted by 1, 2, 3, 4 or 5, preferably 1 or 2, more preferably 1, radicals R10; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R10;


where R7, R8, R9 and R10 have one of the meanings given above or in particular one of the preferred meanings given below.


More preferably, R1 is selected from the group consisting of hydrogen; cyano; C1-C10-alkyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; C1-C10-alkoxy; C1-C10-haloalkoxy; C3-C8-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; C2-C10-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; C2-C10-alkynyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; —C(═O)R6; phenyl which may be substituted by 1, 2, 3, 4 or 5, preferably 1 or 2, more preferably 1, radicals R10; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R10,


where R6 and R10 have one of the meanings given above or in particular one of the preferred meanings given below.


Even more preferably, R1 is selected from the group consisting of hydrogen; cyano; C1-C10-alkyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; C1-C10-alkoxy; C1-C10-haloalkoxy; C3-C8-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6, and —C(═O)R6; where R6 has one of the meanings given above or in particular one of the preferred meanings given below.


In particular, R1 is selected from the group consisting of hydrogen, cyano, C1-C10-alkyl, preferably C1-C6-alkyl, more preferably C1-C4-alkyl, which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; cyclopropyl; C1-C4-alkoxy; C1-C4-haloalkoxy, and —C(═O)R6; where R6 has one of the meanings given above or in particular one of the preferred meanings given below.


Specifically, R1 is selected from the group consisting of hydrogen; cyano; C1-C6-alkyl; C1-C4-haloalkyl, specifically C1-C4-fluoroalkyl; C1-C4-alkoxy; C1-C4-haloalkoxy, specifically C1-C4-fluoroalkoxy; and —C(═O)R6; where R6 has one of the meanings given above or preferably one of the preferred meanings given below. More specifically, R1 is hydrogen.


In case R1 is selected from C1-C10-alkyl, preferably C1-C6-alkyl, more preferably C1-C4-alkyl, which is substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6, R6 is preferably selected from C3-C6-cycloalkyl, C3-C6-halocycloalkyl, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R10, more preferably from a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R10, even more preferably from a 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms selected from N, O and S, as ring members, where the heterocyclic ring may be substituted by one or more, e.g. 1, 2 or 3, preferably 1 or 2, more preferably 1, radicals R10, in particular from a 5- or 6-membered heteroaromatic ring containing 1 heteroatom selected from N, O and S and optionally 1 or two further N atoms, as ring members, where the heteroaromatic ring may be substituted by one or more, e.g. 1, 2 or 3, preferably 1 or 2, more preferably 1, radicals R10, and is specifically 6-membered heteroaromatic ring selected from pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl and 1,3,5-triazinyl, preferably from pyridyl and pyrimidinyl, where the heteroaromatic ring may be substituted by one or more, e.g. 1, 2 or 3, preferably 1 or 2, more preferably 1, radicals R10,


where R10 has one of the meanings given above or in particular one of the preferred meanings given below.


R2 is preferably selected from the group consisting of hydrogen; C1-C10-alkyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; C3-C8-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; C2-C10-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; C2-C10-alkynyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; —C(═O)R6; —C(═O)OR7; —C(═O)N(R8)R9; —C(═S)R6; —C(═S)OR7, —C(═S)N(R8)R9; —C(═NR8)R6, phenyl which may be substituted by 1, 2, 3, 4 or 5, preferably 1 or 2, more preferably 1, radicals R10; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R10,

  • or R2 and R3 together form a group ═CR11R12; ═S(O)mR7; ═S(O)mN(R8)R9; ═NR8; or ═NOR7;
  • or R2 and R3 together form a C2-C7 alkylene chain, thus forming, together with the nitrogen atom to which they are bound, a 3-, 4-, 5-, 6-, 7- or 8-membered ring, where the alkylene chain may be interrupted by 1 or 2 O, S and/or NR18 and/or 1 or 2 of the CH2 groups of the alkylene chain may be replaced by a group C═O, C═S and/or C═NR18; and/or the alkylene chain may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals selected from the group consisting of halogen, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl which may be substituted by 1, 2, 3, 4 or 5, preferably 1 or 2, more preferably 1, radicals R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R10,


    where R6, R7, R8, R9, R10, R11, R12 and R18 have one of the meanings given above or in particular one of the preferred meanings given below.


More preferably, R2 is selected from the group consisting of hydrogen; C1-C10-alkyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; C3-C8-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; C2-C10-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; C2-C10-alkynyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; —C(═O)R6; —C(═O)OR7; —C(═O)N(R8)R9; —C(═S)R6; —C(═S)OR7, —C(═S)N(R8)R9; —C(═NR8)R6, phenyl which may be substituted by 1, 2, 3, 4 or 5, preferably 1 or 2, more preferably 1, radicals R10; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R10,


where R6, R7, R8, R9 and R10 have one of the meanings given above or in particular one of the preferred meanings given below.


In case Y is a chemical bond, R2 is more preferably selected from a substituent bound via a heteroatom, such as —N(R8)R9; —N(R8)C(═O)R6; —OR7; —SR7; —S(O)mR7; —S(O)nN(R8)R9 and an N-bound 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 N atom as ring member and optionally 1 or 2 further heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R10, where R6, R7, R8, R9 and R10 have one of the meanings given above or in particular one of the preferred meanings given below.


In case Y is a chemical bond, R2 is even more preferably selected from —N(R8)R9; —N(R8)C(═O)R6; —OR7; —SR7; —S(O)mR7 and S(O)nN(R8)R9, in particular from —N(R8)R9; —N(R8)C(═O)R6; —OR7 and —SR7, and specifically from —N(R8)R9; —N(R8)C(═O)R6 and —OR7, where R6, R7, R8 and R9 have one of the meanings given above or in particular one of the preferred meanings given below.


In case Y is not a chemical bond, R2 is preferably selected from the group consisting of hydrogen; C1-C10-alkyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; C3-C8-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; C2-C10-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; C2-C10-alkynyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; —C(═O)R6; —C(═O)OR7; —C(═O)N(R8)R9; —C(═S)R6; —C(═S)OR7, —C(═S)N(R8)R9; —C(═NR8)R6, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R10,


where R6, R7, R8, R9 and R10 have one of the meanings given above or in particular one of the preferred meanings given below.


In case Y is not a chemical bond, R2 is more preferably selected from the group consisting of hydrogen; C1-C10-alkyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; C3-C8-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; —C(═O)R6; —C(═O)OR7; —C(═O)N(R8)R9; —C(═S)R6; —C(═S)OR7, —C(═S)N(R8)R9; —C(═NR8)R6, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R10,


where R6, R7, R8, R9 and R10 have one of the meanings given above or in particular one of the preferred meanings given below.


Independently from the meaning of Y, R2 is even more preferably selected from the group consisting of C1-C4-alkyl; C1-C4-haloalkyl; a methyl group substituted by a radical R6; —C(═O)R6; —C(═O)N(R8)R9; —C(═O)OR7; —C(═S)R6; —C(═S)N(R8)R9; —C(═S)OR7; and —C(═NR8)R6; and specifically from —C(═O)N(R8)R9 and —C(═S)N(R8)R9; where R6, R7, R8 and R9 have one of the meanings given above or in particular one of the preferred meanings given below. It is however preferred that R2 has these meanings if Y is not a chemical bond and is preferably O or NR3, specifically NR3.


Independently from the meaning of Y, R2 is particularly preferably selected from the group consisting of C1-C4-alkyl; C1-C4-haloalkyl; a methyl group substituted by a radical R6a; —C(═O)R6c; —C(═O)N(R8)R9; —C(═O)OR7; —C(═S)R6c; —C(═S)N(R8)R9; —C(═S)OR7; and —C(═NR8)R6d; and specifically from —C(═O)N(R8)R9 and —C(═S)N(R8)R9;


where




  • R6a is selected from CN, phenyl which may carry 1, 2 or 3, preferably 1 or 2, more preferably 1, substituents R10, —C(═O)R6b; —C(═O)N(R8)R9 and —C(═O)OR7;

  • R6b and R6c are independently selected from C1-C4-alkyl, C1-C4-haloalkyl, phenyl, benzyl and a 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the phenyl or heterocyclyl rings in the three last-mentioned radicals may carry 1, 2 or 3, preferably 1 or 2, more preferably 1, substituents selected from halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;

  • R6d is selected from N(R8)R9;

  • R7 is selected from hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, phenyl, benzyl and a 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the phenyl or heterocyclyl rings in the three last-mentioned radicals may carry 1, 2 or 3, preferably 1 or 2, more preferably 1, substituents selected from halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;

  • each R8 is independently selected from hydrogen, cyano, C1-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, C2-C4-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, C3-C6-halocycloalkyl-C1-C4-alkyl, —S(O)mR20—S(O)nN(R21)R22, phenyl, benzyl and a 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the phenyl or heterocyclyl rings in the three last-mentioned radicals may carry 1, 2 or 3, preferably 1 or 2, more preferably 1, substituents selected from halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;

  • each R9 is independently selected from hydrogen, cyano, C1-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, C2-C4-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, C3-C6-halocycloalkyl-C1-C4-alkyl, —S(O)mR20, —S(O)nN(R21)R22, phenyl, benzyl and a 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the phenyl or heterocyclyl rings in the three last-mentioned radicals may carry 1, 2 or 3, preferably 1 or 2, more preferably 1, substituents selected from halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy; and

  • R10 is selected from halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;
    • where R19 has one of the meanings given above or in particular one of the preferred meanings given below; or

  • R8 and R9 together form a group ═CR11R12; or

  • R8 and R9, together with the nitrogen atom to which they are bound, form a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring which may additionally containing 1 or 2 further heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10.



It is however preferred that R2 has these meanings if Y is not a chemical bond and is preferably O or NR3, specifically NR3.


In particular, R2 is selected from —C(═O)N(R8)R9 and —C(═S)N(R8)R9, where R8 and R9 have one of the meanings given above or in particular one of the preferred meanings given below. More preferably, R2 is selected from —C(═O)N(R8)R9 and —C(═S)N(R8)R9, where

  • R8 is selected from hydrogen and C1-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19;
  • R9 is selected from hydrogen, C1-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl and C3-C6-halocycloalkyl-C1-C4-alkyl; and
  • R19 has one of the meanings given above or in particular one of the preferred meanings given below.


It is preferred that R2 has these meanings if Y is not a chemical bond and is preferably O or NR3, specifically NR3.


Specifically, R2 is selected from —C(═O)N(R8)R9 and —C(═S)N(R8)R9, where

  • R8 is hydrogen; and
  • R9 is selected from hydrogen, C1-C6-alkyl; C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl and C3-C6-halocycloalkyl-C1-C4-alkyl.


It is preferred that R2 has these meanings if Y is not a chemical bond and is preferably O or NR3, specifically NR3.


R3 is preferably selected from the group consisting of hydrogen; cyano; C1-C10-alkyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; C3-C8-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; C2-C10-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; C2-C10-alkynyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; —N(R8)R9; —Si(R14)2R13; —OR7; —SR7; —S(O)mR7; —S(O)nN(R8)R9; —C(═O)R6; —C(═O)OR7; —C(═O)N(R8)R9; —C(═S)R6; —C(═S)OR7; —C(═S)N(R8)R9; —C(═NR8)R6; phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10;

  • or R2 and R3 together form a group ═CR11R12; ═S(O)mR7; ═S(O)mN(R8)R9; ═NR8; or ═NOR7;
  • or R2 and R3 together form a C2-C7 alkylene chain, thus forming, together with the nitrogen atom to which they are bound, a 3-, 4-, 5-, 6-, 7- or 8-membered ring, where the alkylene chain may be interrupted by 1 or 2 O, S and/or NR18 and/or 1 or 2 of the CH2 groups of the alkylene chain may be replaced by a group C═O, C═S and/or C═NR18; and/or the alkylene chain may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals selected from the group consisting of halogen, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl which may be substituted by 1, 2, 3, 4 or 5, preferably 1 or 2, more preferably 1, radicals R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R10,


    where R6, R7, R8, R9, R10, R11, R12, R13, R14 and R18 have one of the meanings given above or in particular one of the preferred meanings given below.


More preferably, R3 is selected from the group consisting of hydrogen; C1-C10-alkyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; C3-C8-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; C2-C10-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; C2-C10-alkynyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; —C(═O)R6; —C(═O)OR7; —C(═O)N(R8)R9; —C(═S)R6; —C(═S)OR7; —C(═S)N(R8)R9; —C(═NR8)R6; phenyl which may be substituted by 1, 2, 3, 4 or 5, preferably 1 or 2, more preferably 1, radicals R10; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R10,


where R6, R7, R8, R9 and R10 have one of the meanings given above or in particular one of the preferred meanings given below.


Even more preferably, R3 is selected from the group consisting of hydrogen; C1-C10-alkyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; —C(═O)R6; —C(═O)OR7; —C(═O)N(R8)R9; —C(═S)R6; —C(═S)OR7; —C(═S)N(R8)R9 and —C(═NR8)R6; where R6, R7, R8 and R9 have one of the meanings given above and in particular one of the preferred meanings given below. Preferably, in this case, R6 as a C1-C6-alkyl substituent, is selected from CN, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio and a 5- or 6-membered hetaryl ring containing 1, 2 or 3 heteroatoms selected from N, O and S as ring members and being optionally substituted by 1, 2 or 3 radicals R10. In this case, R6 as a CO substituent, is preferably selected from C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy. In this case, R8 and R9 are preferably selected from hydrogen and C1-C6-alkyl.


In particular, R3 is selected from the group consisting of hydrogen; C1-C6-alkyl and C1-C4-haloalkyl and is specifically hydrogen.


Preferably, each R4 is independently selected from halogen; cyano; nitro; —SCN; SF5; C1-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; C3-C8-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; C2-C6-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; C2-C6-alkynyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; —Si(R14)2R13; —OR7; —OS(O)nR7; —SR7; —S(O)mR7; —S(O)nN(R8)R9; —N(R8)R9; —N(R8)C(═O)R6; C(═O)R6; —C(═O)OR7; —C(═NR8)H; —C(═NR8)R6; —C(═O)N(R8)R9; C(═S)N(R8)R9; phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R10;

  • or two radicals R4 bound on adjacent carbon atoms may be together a group selected from —CH2CH2CH2CH2—, —CH═CH—CH═CH—, —N═CH—CH═CH—, —CH═N—CH═CH—, —N═CH—N═CH—, —OCH2CH2CH2—, —OCH═CHCH2— —CH2OCH2CH2—, —CH2CH2CH2—, —OCH2CH2O—, —OCH2OCH2—, —CH2CH2CH2—, —CH═CHCH2—, —CH2CH2O—, —CH═CHO—, —CH2OCH2—, —CH2C(═O)O—, —C(═O)OCH2—, —O(CH2)O—, —SCH2CH2CH2—, —SCH═CHCH2—, —CH2SCH2CH2—, —SCH2CH2—, —SCH2SCH2— —CH2CH2S—, —CH═CHS—, —CH2SCH2—, —CH2C(═S)S—, —C(═S)SCH2—, —S(CH2)S—, —CH2CH2NR8—, —CH2CH═N—, —CH═CH—NR8—, —OCH═N—, and —SCH═N—, thus forming, together with the carbon atoms to which they are bound, a 5- or 6-membered ring, where the hydrogen atoms of the above groups may be replaced by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, substituents selected from halogen, methyl, halomethyl, hydroxyl, methoxy and halomethoxy or one or more, e.g. 1 or 2, CH2 groups of the above groups may be replaced by a C═O group,


    where R6, R7, R8, R9, R10, R13 and R14 have one of the meanings given above or in particular one of the preferred meanings given below.


More preferably, each R4 is independently selected from halogen; cyano; nitro; —SCN; C1-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; C3-C8-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; —OR7; —OS(O)nR7; —SR7; —S(O)nR7; —S(O)nN(R8)R9; —N(R8)R9; —N(R8)C(═O)R6; C(═O)R6; —C(═O)OR7; —C(═NR8)R6; —C(═O)N(R8)R9; —C(═S)N(R8)R9; phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R10;

  • or two radicals R4 bound on adjacent carbon atoms may be together a group selected from —CH2CH2CH2CH2—, —CH═CH—CH═CH—, —N═CH—CH═CH—, —CH═N—CH═CH—, —N═CH—N═CH—, —OCH2CH2CH2—, —OCH═CHCH2—, —CH2OCH2CH2—, —OCH2CH2O—, —OCH2OCH2—, —CH2CH2CH2—, —CH═CHCH2—, —CH2CH2O—, —CH═CHO—, —CH2OCH2—, —CH2C(═O)O—, —C(═O)OCH2—, —O(CH2)O—, —SCH2CH2CH2—, —SCH═CHCH2—, —CH2SCH2CH2—, —CH2CH2S—, —CH═CHS—, —CH2SCH2—, —CH2CH2NR8—, —CH2CH═N—, —OCH═N—, and —SCH═N—, thus forming, together with the carbon atoms to which they are bound, a 5- or 6-membered ring, where the hydrogen atoms of the above groups may be replaced by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, substituents selected from halogen, methyl, halomethyl, hydroxyl, methoxy and halomethoxy or one or more, e.g. 1 or 2, CH2 groups of the above groups may be replaced by a C═O group,


    where R6, R7, R8, R9 and R10 have one of the meanings given above or in particular one of the preferred meanings given below.


Even more preferably, each R4 is independently selected from halogen; cyano; nitro; —SCN; C1-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; C3-C8-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; —OR7; —OS(O)nR7; —SR7; —S(O)mR7; —S(O)nN(R8)R9; —N(R8)R9; C(═O)R6; —C(═O)OR7; —C(═NR8)R6; —C(═O)N(R8)R9; —C(═S)N(R8)R9 and phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10


where R6, R7, R8, R9 and R10 have one of the meanings given above or in particular one of the preferred meanings given below.


In particular, each R4 is independently selected from halogen; cyano; nitro; C1-C6-alkyl; C1-C6-haloalkyl; C1-C6-alkoxy; C1-C6-haloalkoxy; and phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10;

  • or two radicals R4 bound on adjacent carbon atoms may be together a group selected from —CH2CH2CH2CH2— and —CH═CH—CH═CH— and preferably —CH═CH—CH═CH—,


    where R10 has one of the meanings given above or in particular one of the preferred meanings given below.


More particularly, each R4 is independently selected from halogen, cyano, C1-C6-alkyl, preferably C1-C4-alkyl, more preferably methyl, and C1-C4-haloalkyl, preferably C1-C2-haloalkyl. Specifically, each R4 is independently selected from halogen and C1-C4-alkyl and is very specifically chlorine or methyl.


Preferably, each R5 is independently selected from the group consisting of halogen, cyano, nitro, —SCN, SF5, C1-C6-alkyl, C1-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6, C3-C8-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6, C2-C6-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6, C2-C6-alkynyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6, Si(R14)2R13, OR7, OS(O)nR7, S(O)mR7, NR8R9, N(R8)C(═O)R6, C(═O)R6, C(═O)OR7, C(═NR8)R6, C(═S)NR6, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R10,


where R6, R7, R8, R9, R10, R13 and R14 have one of the meanings given above or in particular one of the preferred meanings given below.


More preferably, each R5 is independently selected from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, C1-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6, OR7, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R10,


where R6, R7 and R10 have one of the meanings given above or in particular one of the preferred meanings given below.


Even more preferably, each R5 is independently selected from the group consisting of halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy, in particular from halogen, C1-C4-alkyl and C1-C2-haloalkyl and is specifically halogen, more specifically chlorine, or C1-C2-haloalkyl, specifically CF3.


In case R6 is a substituent on an alkyl, alkenyl or alkynyl group, it is preferably selected from the group consisting of cyano, azido, nitro, —SCN, SF5, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, —Si(R14)2R13, —OR7, —OSO2R7, —SR7, —S(O)mR7, —S(O)nN(R8)R9, —N(R8)R9, —C(═O)N(R8)R9, —C(═S)N(R8)R9, —C(═O)OR7, —C(═O)R19, —C(═NR8)R19, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10; or two geminally bound radicals R6 together form a group selected from ═CR11R12, ═S(O)mR7, ═S(O)mN(R8)R9, ═NR8, ═NOR7 and ═NNR8; or two radicals R6, together with the carbon atoms to which they are bound, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated carbocyclic or heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members,


where R7, R8, R9, R10, R11, R12, R13, R14 and R19 have one of the meanings given above or in particular one of the preferred meanings given below.


In case R6 is a substituent on an alkyl, alkenyl or alkynyl group, it is more preferably selected from the group consisting of cyano, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, —OR7, —SR7, —C(═O)N(R8)R9, —C(═S)N(R8)R9, —C(═O)OR7, —C(═O)R19, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10;


where R7, R8, R9 and R10 have one of the meanings given above or in particular one of the preferred meanings given below.


In case R6 is a substituent on an alkyl, alkenyl or alkynyl group, it is even more preferably selected from the group consisting of cyano, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, —C(═O)N(R8)R9, —C(═S)N(R8)R9, —C(═O)OR7, —C(═O)R19, phenyl which may be substituted by 1, 2, 3, 4 or radicals R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10;


where R10 has one of the meanings given above or in particular one of the preferred meanings given below.


In case R6 is a substituent on an alkyl, alkenyl or alkynyl group, it is in particular selected from the group consisting of cyano, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, —C(═O)N(R8)R9, —C(═S)N(R8)R9, —C(═O)OR7, —C(═O)R19, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10;


where R10 has one of the meanings given above or in particular one of the preferred meanings given below.


In case R6 is a substituent on a cycloalkyl group, it is preferably selected from the group consisting of cyano, azido, nitro, —SCN, SF5, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, —Si(R14)2R13, —OR7, —OSO2R7, —SR7, —S(O)mR7, —S(O)nN(R8)R9, —N(R8)R9, —C(═O)N(R8)R9, —C(═S)N(R8)R9, —C(═O)OR7, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10;

  • or two geminally bound radicals R6 together form a group selected from ═CR11R12 ═S(O)mR7, ═S(O)mN(R8)R9, ═NR8, ═NOR7 and ═NNR8;
  • or two radicals R6, together with the carbon atoms to which they are bound, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated carbocyclic or heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members,


    where R7, R8, R9, R10, R11, R12, R13 and R14 have one of the meanings given above or in particular one of the preferred meanings given below.


In case R6 is a substituent on a cycloalkyl group, it is more preferably selected from the group consisting of halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, —OR7, —OSO2R7, —SR7, —S(O)mR7, —S(O)nN(R8)R9, —N(R8)R9, —C(═O)N(R8)R9, —C(═S)N(R8)R9, —C(═O)OR7, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10;


where R7, R8, R9 and R10 have one of the meanings given above or in particular one of the preferred meanings given below.


In case R6 is a substituent on a cycloalkyl group, it is even more preferably selected from the group consisting of halogen, C1-C4-alkyl, C1-C3-haloalkyl, C1-C4-alkoxy and C1-C3-haloalkoxy. In particular, R6 as a substituent on a cycloalkyl group is selected from halogen, C1-C4-alkyl and C1-C3-haloalkyl.


In case R6 is a substituent on C(═O), C(═S) or C(═NR8), it is preferably selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, —OR7, —SR7, —N(R8)R9, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10;


where R7, R8, R9 and R10 have one of the meanings given above or in particular one of the preferred meanings given below.


In case R6 is a substituent on C(═O), C(═S) or C(═NR8), it is more preferably selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10;


where R10 has one of the meanings given above or in particular one of the preferred meanings given below.


In case R6 is a substituent on C(═O), C(═S) or C(═NR8), it is more preferably selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10;


where R10 has one of the meanings given above or in particular one of the preferred meanings given below.


In case R6 is a substituent on C(═O), C(═S) or C(═NR8), it is even more preferably selected from the group consisting of C1-C4-alkyl, C1-C3-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C4-alkoxy, C1-C3-haloalkoxy, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, and a 5- or 6-membered heteroaromatic ring containing 1, 2 or 3 heteroatoms selected from N, O and S, as ring members, where the heteroaromatic ring may be substituted by one or more radicals R10;


where R10 has one of the meanings given above or in particular one of the preferred meanings given below.


Preferably, each R7 is independently selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C3-C8-cycloalkylC1-C4-alkyl, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R10, where R10 has one of the meanings given above or in particular one of the preferred meanings given below.


More preferably, each R7 is independently selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10; and a 5- or 6-membered heteroaromatic ring containing 1, 2 or 3 heteroatoms selected from N, O and S, as ring members, where the heteroaromatic ring may be substituted by one or more radicals R10; where R10 has one of the meanings given above or in particular one of the preferred meanings given below.


R8 and R9 are independently of each other and independently of each occurrence preferably selected from the group consisting of hydrogen, cyano, C1-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, C2-C6-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, C2-C6-alkynyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C3-C8-cycloalkyl-C1-C6-alkyl, S(O)mR20, S(O)nNR21R22, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, benzyl wherein the phenyl moiety may be substituted by 1, 2, 3, 4 or 5 radicals R10, and a 5- or 6-membered heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10; where R10 has one of the meanings given above or in particular one of the preferred meanings given below; or

  • R8 and R9 together form a group ═CR11R12; or
  • R8 and R9, together with the nitrogen atom to which they are bound, form a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic, preferably a saturated, heterocyclic ring which may additionally containing 1 or 2 further heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10.


In the above preferred embodiment of R8 and R9, R11 is preferably hydrogen or methyl and R12 is preferably C1-C6-alkoxy, C1-C6-haloalkoxy, —C(═O)R19, —C(═O)OR20, or —C(═O)N(R21)R22.


In the above preferred embodiment of R8 and R9, R9, if it does not form together with R8 a group ═CR11R12 or together with R8 and the N atom to which they are bound a heterocyclic ring, is preferably selected from hydrogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, cyclopropyl, C1-C4-alkylcarbonyl, C1-C4-haloalkylcarbonyl, C1-C4-alkoxycarbonyl and C1-C4-haloalkoxycarbonyl and is more preferably hydrogen or C1-C4-alkyl.


In the above preferred embodiment of R8 and R9, R8, if it does not form together with R9 a group ═CR11R12 or together with R9 and the N atom to which they are bound a heterocyclic ring, is preferably selected from CN, C1-C6-alkyl; C1-C6-haloalkyl; C1-C4-alkyl which carries one radical R19; C2-C6-alkenyl; C2-C6-haloalkenyl; C2-C4-alkenyl which is substituted by one radical R19; C3-C6-cycloalkyl; C3-C6-halocycloalkyl; C3-C6-cycloalkylC1-C4-alkyl; C3-C6-halocycloalkyl-C1-C4-alkyl; —S(O)mR20; —S(O)nN(R21)R22; phenyl; benzyl and a 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the phenyl or heterocyclyl rings in the three last-mentioned radicals may carry 1, 2 or 3 substituents selected from halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy.


If R8 and R9, together with the nitrogen atom to which they are bound, form a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring which may additionally contain 1 or 2 further heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, this is preferably a 3, 5 or 6-membered saturated heterocyclic ring which may additionally contain 1 further heteroatom or heteroatom group selected from N, O, S, NO, SO and SO2, as ring member.


Specifically, R8 and R9 are independently of each other and independently of each occurrence selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkynyl, C3-C8-cycloalkyl-C1-C6-alkyl, benzyl wherein the phenyl moiety may be substituted by 1, 2, 3, 4 or 5 radicals R10, and a 5- or 6-membered heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10. More specifically, R9 is hydrogen or C1-C4-alkyl and R8 has one of the meanings specified above.


Preferably, each R10 is independently selected from the group consisting of halogen, cyano, C1-C10-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, C3-C8-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, —OR20, —OS(O)nR20, —SR20, —S(O)mR20, —S(O)nN(R21)R22, —N(R21)R22, C(═O)R19, —C(═O)OR20, —C(═O)N(R21)R21, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals independently selected from halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy; and a 3-, 4-, 5-, 6- or 7-membered saturated or unsaturated heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, which may be substituted by one or more radicals independently selected from halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy;

  • or two radicals R10 bound on adjacent atoms together form a group selected from —CH2CH2CH2CH2—, —CH═CH—CH═CH—, —N═CH—CH═CH—, —CH═N—CH═CH—, —N═CH—N═CH—, —OCH2CH2CH2—, —OCH═CHCH2—, —CH2OCH2CH2—, —OCH2CH2O—, —OCH2OCH2—, —CH2CH2CH2—, —CH═CHCH2—, —CH2CH2O—, —CH═CHO—, —CH2OCH2—, —CH2C(═O)O—, —C(═O)OCH2—, and —O(CH2)O—, thus forming, together with the atoms to which they are bound, a 5- or 6-membered ring, where the hydrogen atoms of the above groups may be replaced by one or more substituents selected from halogen, methyl, halomethyl, hydroxyl, methoxy and halomethoxy or one or more CH2 groups of the above groups may be replaced by a C═O group,


    where R19, R20, R21 and R22 have one of the general or in particular one of the preferred meanings given above.


More preferably, each R10 is independently selected from the group consisting of halogen, cyano, C1-C10-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, —OR20, —N(R21)R22, C(═O)R19, —C(═O)OR20, —C(═O)N(R21)R22, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals independently selected from halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy; and a 3-, 4-, 5-, 6- or 7-membered saturated or unsaturated heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, which may be substituted by one or more radicals independently selected from halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy;


where R19, R20, R21 and R22 have one of the general or in particular one of the preferred meanings given above.


Even more preferably, each R10 is independently selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy. In particular, each R10 is independently selected from the group consisting of halogen, C1-C4-alkyl and C1-C4-haloalkyl and is specifically halogen, more specifically chlorine.


Preferably, R11 and R12 are, independently of each other and independently of each occurrence, selected from the group consisting of hydrogen, halogen, C1-C6-alkyl and C1-C6-haloalkyl. More preferably, R11 and R12 are, independently of each other and independently of each occurrence, selected from the group consisting of hydrogen, halogen and C1-C6-alkyl and in particular from the group consisting of hydrogen and halogen. Specifically, they are hydrogen.


Preferably, R13 and R14 are, independently of each other and independently of each occurrence, selected from C1-C4-alkyl and are in particular methyl.


Preferably, R15 and R16 are, independently of each other and independently of each occurrence, selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl and phenyl which may be substituted by 1, 2, 3, 4, or 5 radicals R10; where R10 has one of the general or in particular one of the preferred meanings given above.


Preferably, each R17 is independently selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, phenyl and benzyl. More preferably, each R17 is independently selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl and phenyl and is in particular C1-C4-alkyl or C1-C3-haloalkyl.


Preferably, each R18 is independently selected from the group consisting of hydrogen; C1-C10-alkyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; —C(═O)R6; —C(═O)OR7; —C(═O)N(R8)R9; —C(═S)R6; —C(═S)OR7; —C(═S)N(R8)R9 and —C(═NR8)R6; where R6, R7, R8 and R9 have one of the general or in particular one of the preferred meanings given above.


More preferably, each R18 is selected from the group consisting of hydrogen; C1-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1, radicals R6; —C(═O)R6 and —C(═O)N(R8)R9; where R6, R8 and R9 have one of the general or in particular one of the preferred meanings given above. Preferably, in this case, R6 as a C1-C6-alkyl substituent, is selected from CN, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio and a 5- or 6-membered hetaryl ring containing 1, 2 or 3 heteroatoms selected from N, O and S as ring members and being optionally substituted by 1, 2 or 3 radicals R10. In this case, R6 as a CO substituent, is preferably selected from C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy. In this case, R8 and R9 are preferably selected from hydrogen and C1-C6-alkyl.


In particular, each R18 is selected from the group consisting of hydrogen, C1-C4-alkyl, C1-C4-haloalkyl and —C(═O)R6, and is specifically selected from the group consisting of hydrogen, C1-C4-alkyl and —C(═O)R6, where R6 has one of the general or in particular one of the preferred meanings given above and is specifically C1-C4-alkyl.


In case R19 is a substituent on an alkyl, alkenyl or alkynyl group, it is preferably selected from the group consisting of cyano, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, —OR20, —C(═O)N(R21)R22, —C(═S)N(R21)R22, —C(═O)OR20, —C(═O)R20, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, and a 5- or 6-membered heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the rings in the three last-mentioned radicals may be substituted by one or more radicals R10; where

  • R10 is selected from halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;
  • R20 is selected from hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, phenyl, benzyl, and a 5- or 6-membered heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the rings in the three last-mentioned radicals may be substituted by one or more radicals R10; and
  • R21 and R22, independently of each other and independently of each occurrence, are selected from hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, phenyl, benzyl, and a 5- or 6-membered heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the rings in the three last-mentioned radicals may be substituted by one or more radicals R10.


In case R19 is a substituent on a cycloalkyl group, it is preferably selected from the group consisting of cyano, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, —C(═O)N(R21)R22, —C(═S)N(R21)R22, —C(═O)OR20, —C(═O)R20, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, and a 5- or 6-membered heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the rings in the three last-mentioned radicals may be substituted by one or more radicals R10; where

  • R10 is selected from halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;
  • R20 is selected from hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, phenyl, benzyl, and a 5- or 6-membered heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the rings in the three last-mentioned radicals may be substituted by one or more radicals R10; and
  • R21 and R22, independently of each other and independently of each occurrence, are selected from hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, phenyl, benzyl, and a 5- or 6-membered heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the rings in the three last-mentioned radicals may be substituted by one or more radicals R10.


In case R19 is a substituent on a C(═O) group, it is preferably selected from the group consisting of hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, benzyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, and a 5- or 6-membered heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the rings in the three last-mentioned radicals may be substituted by one or more radicals R10; where R10 is selected from halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy.


R20 is preferably selected from the group consisting of hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, benzyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, and a 5- or 6-membered heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the rings in the three last-mentioned radicals may be substituted by one or more radicals R10; where R10 is selected from halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy.


R21 and R22, independently of each other and independently of each occurrence, are preferably selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, benzyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, and a 5- or 6-membered heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the rings in the three last-mentioned radicals may be substituted by one or more radicals R10; where R10 is selected from halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;

  • or R21 and R22, together with the nitrogen atom to which they are bound, may form a 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic ring which may additionally containing 1 or 2 further heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals selected from halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy.


One particularly preferred embodiment of the invention refers to compounds of the formula I-1




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where X1 is O or S and X, R1, R3, R4, R5, R8, R9, p and q have one of the above-given general or, in particular, one of the above-given preferred meanings.


In particular, the invention relates to compounds I-1, where

  • X1 is O or S;
  • p is 0, 1 or 2;
  • q is 0, 1, 2 or 3; and
  • X, R1, R3, R4, R5, R8 and R9 have one of the above-given general or, in particular, one of the above-given preferred meanings.


In compounds of the formula I-1, R1 is preferably hydrogen.


In compounds of the formula I-1, R3 is preferably hydrogen.


In compounds of the formula I-1, R4 is preferably halogen, cyano, C1-C4-alkyl or C1-C4-haloalkyl, more preferably halogen or C1-C4-alkyl and specifically chlorine or methyl.


In compounds of the formula I-1, R5 is preferably halogen or C1-C4-haloalkyl, more preferably chlorine or CF3 and specifically chlorine.


In compounds of the formula I-1, R8 is preferably selected from hydrogen and C1-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, where R19 has one of the above-given general or, in particular, one of the above-given preferred meanings; R8 is specifically hydrogen.


In compounds of the formula I-1, R9 is preferably is selected from hydrogen, C1-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl and C3-C6-halocycloalkyl-C1-C4-alkyl, and more preferably from hydrogen, C1-C6-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl and C3-C6-cycloalkyl-methyl.


In compounds of the formula I-1, X is preferably selected from CF3, CHF2 and CF2Cl and is more preferably CF3.


Particularly preferably, in compounds I-1X

  • X1 is O or S;
  • X is CF3;
  • R1 is hydrogen;
  • R3 is hydrogen;
  • R4 is halogen or C1-C4-alkyl, preferably chlorine or methyl;
  • R5 is chlorine or CF3, preferably chlorine;
  • R8 is hydrogen;
  • R9 is selected from hydrogen, C1-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl and C3-C6-halocycloalkyl-C1-C4-alkyl, preferably from hydrogen, C1-C6-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl and C3-C6-cycloalkyl-methyl;
  • p is 0, 1 or 2, preferably 1; and
  • q is 0, 1, 2 or 3, preferably 2.


As already mentioned, a preferred embodiment of the compounds of the present invention is enantiomer I-A




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wherein the variables have one of the above-given general, or in particular one of the above-given preferred meanings. Preferably, X in compounds I-A is CF3.


A more preferred embodiment relates to compounds I-A.1




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where

  • X1 is O or S;
  • p is 0, 1 or 2;
  • q is 0, 1, 2 or 3; and
  • X, R1, R3, R4, R5, R8 and R9 have one of the above-given general or, in particular, one of the above-given preferred meanings.


In compounds of the formula I-A.1, R1 is preferably hydrogen.


In compounds of the formula I-A.1, R3 is preferably hydrogen.


In compounds of the formula I-A.1, R4 is preferably halogen, cyano, C1-C4-alkyl or C1-C4-haloalkyl, more preferably halogen or C1-C4-alkyl and specifically chlorine or methyl.


In compounds of the formula I-A.1, R5 is preferably halogen or C1-C4-haloalkyl, more preferably chlorine or CF3 and specifically chlorine.


In compounds of the formula I-A.1, R8 is preferably selected from hydrogen and C1-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, where R19 has one of the above-given general or, in particular, one of the above-given preferred meanings; R8 is specifically hydrogen.


In compounds of the formula I-A.1, R9 is preferably is selected from hydrogen, C1-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl and C3-C6-halocycloalkyl-C1-C4-alkyl, and more preferably from hydrogen, C1-C6-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl and C3-C6-cycloalkyl-methyl.


In compounds of the formula I-A.1, X is preferably selected from CF3, CHF2 and CF2Cl and is more preferably CF3.


Particularly preferably, in compounds I-A.1

  • X1 is O or S;
  • X is CF3;
  • R1 is hydrogen;
  • R3 is hydrogen;
  • R4 is halogen or C1-C4-alkyl, preferably chlorine or methyl;
  • R5 is chlorine or CF3, preferably chlorine;
  • R8 is hydrogen;
  • R9 is selected from hydrogen, C1-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl and C3-C6-halocycloalkyl-C1-C4-alkyl, preferably from hydrogen, C1-C6-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl and C3-C6-cycloalkyl-methyl;
  • p is 0, 1 or 2, preferably 1; and
  • q is 0, 1, 2 or 3, preferably 2.


Examples of preferred compounds are compounds of the following formulae I.1 to 1.66, where the variables have one of the general or preferred meanings given above. Examples of preferred compounds which are represented by the formulae I.1 to I.66 are the individual compounds compiled in the tables 1 to 24420 below, where the variables Y and R2 have the meanings given in one row of table A. Moreover, the meanings mentioned for the individual variables in the tables are per se, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituents in question.




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Table 1


Compounds of the formula I.1 in which R5a and R5c are chlorine, R5b is H and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Table 2


Compounds of the formula I.1 in which R5a and R5c are bromine, R5b is H and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Table 3


Compounds of the formula I.1 in which R5a and R5c are fluorine, R5b is H and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Table 4


Compounds of the formula I.1 in which R5a and R5c are methyl, R5b is H and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Table 5


Compounds of the formula I.1 in which R5a and R5c are CF3, R5b is H and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Table 6


Compounds of the formula I.1 in which R5a is chlorine and R5b and R5c are H and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Table 7


Compounds of the formula I.1 in which R5a is CF3 and R5b and R5c are H and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Table 8


Compounds of the formula I.1 in which R5a, R5b and R5c are chlorine and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Table 9


Compounds of the formula I.1 in which R5a, R5b and R5c are fluorine and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Table 10


Compounds of the formula I.1 in which R5a and R5c are chlorine and R5b is fluorine and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 11 to 20


Compounds of the formula I.2 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 21 to 30


Compounds of the formula I.3 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 31 to 40


Compounds of the formula I.4 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 41 to 50


Compounds of the formula I.5 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 51 to 60


Compounds of the formula I.6 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 61 to 70


Compounds of the formula I.7 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 71 to 80


Compounds of the formula I.8 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 81 to 90


Compounds of the formula I.9 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 91 to 100


Compounds of the formula I.10 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 101 to 110


Compounds of the formula I.11 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 111 to 120


Compounds of the formula I.12 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 121 to 130


Compounds of the formula I.13 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 131 to 140


Compounds of the formula I.14 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 141 to 150


Compounds of the formula I.15 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 151 to 160


Compounds of the formula I.16 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 161 to 170


Compounds of the formula I.17 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 171 to 180


Compounds of the formula I.18 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 181 to 190


Compounds of the formula I.19 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 191 to 200


Compounds of the formula I.20 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 201 to 210


Compounds of the formula I.21 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 211 to 220


Compounds of the formula I.22 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 221 to 230


Compounds of the formula I.23 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 231 to 240


Compounds of the formula I.24 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 241 to 250


Compounds of the formula I.25 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 251 to 260


Compounds of the formula I.26 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 261 to 270


Compounds of the formula I.27 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 271 to 280


Compounds of the formula I.28 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 281 to 290


Compounds of the formula I.29 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 291 to 300


Compounds of the formula I.30 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 301 to 310


Compounds of the formula I.31 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 311 to 320


Compounds of the formula I.32 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 321 to 330


Compounds of the formula I.33 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 331 to 340


Compounds of the formula I.34 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 341 to 350


Compounds of the formula I.35 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 351 to 360


Compounds of the formula I.36 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 361 to 370


Compounds of the formula I.37 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 371 to 380


Compounds of the formula I.38 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 381 to 390


Compounds of the formula I.39 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 391 to 400


Compounds of the formula I.40 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 401 to 410


Compounds of the formula I.41 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 411 to 420


Compounds of the formula I.42 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 421 to 430


Compounds of the formula I.43 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 431 to 440


Compounds of the formula I.44 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 441 to 450


Compounds of the formula I.45 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 451 to 460


Compounds of the formula I.46 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 461 to 470


Compounds of the formula I.47 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 471 to 480


Compounds of the formula I.48 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 481 to 490


Compounds of the formula I.49 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 491 to 500


Compounds of the formula I.50 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 501 to 510


Compounds of the formula I.51 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 511 to 520


Compounds of the formula I.52 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 521 to 530


Compounds of the formula I.53 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 531 to 540


Compounds of the formula I.54 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 541 to 550


Compounds of the formula I.55 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 551 to 560


Compounds of the formula I.56 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 561 to 570


Compounds of the formula I.57 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 571 to 580


Compounds of the formula I.58 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 581 to 590


Compounds of the formula I.59 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 591 to 600


Compounds of the formula I.60 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 601 to 610


Compounds of the formula I.61 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 611 to 620


Compounds of the formula I.62 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 621 to 630


Compounds of the formula I.63 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 631 to 640


Compounds of the formula I.64 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 641 to 650


Compounds of the formula I.65 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.


Tables 651 to 660


Compounds of the formula I.66 in which the combination of R5a, R5b and R5c is as defined in Tables 1 to 10 and the combination of Y and R2 for a compound corresponds in each case to one row of Table A.











TABLE A





No.
Y
R2







  1.
O
H


  2.
O
CH3


  3.
O
CF3


  4.
O
CH2CH3


  5.
O
CH2CF3


  6.
O
CH2CH2CH3


  7.
O
CH2CH2CF3


  8.
O
CH2CF2CF3


  9.
O
CH(CH3)2


 10.
O
(CH2)3CH3


 11.
O
(CH2)3CF3


 12.
O
CH2-cpropyl


 13.
O
CH(CH3)-cpropyl


 14.
O
CH2CN


 15.
O
CH2C(═O)OH


 16.
O
CH2C(═O)OCH3


 17.
O
CH2C(═O)OCH2CH3


 18.
O
CH2C(═O)OCH2CH2CH3


 19.
O
CH2C(═O)OCH(CH3)2


 20.
O
CH2C(═O)O(CH2)3CH3


 21.
O
CH2C(═O)OCH2CH(CH3)2


 22.
O
CH2C(═O)OC(CH3)3


 23.
O
CH2C(═O)NH2


 24.
O
CH2C(═O)NHCH3


 25.
O
CH2C(═O)N(CH3)2


 26.
O
CH2C(═O)NHCF3


 27.
O
CH2C(═O)N(CF3)2


 28.
O
CH2C(═O)NHCH2CH3


 29.
O
CH2C(═O)N(CH2CH3)2


 30.
O
CH2C(═O)NHCH2CF3


 31.
O
CH2C(═O)N(CH2CF3)2


 32.
O
CH2C(═O)NHCH2CH2CH3


 33.
O
CH2C(═O)NHCH(CH3)2


 34.
O
CH2C(═O)NH(CH2)3CH3


 35.
O
CH2C(═O)NHCH2-cpropyl


 36.
O
CH2C(═O)NHCH2—C6H5


 37.
O
CH2C(═O)NH-propargyl


 38.
O
CH2C(═O)NHCH2-4-Cl—C6H4


 39.
O
CH2C(═O)-morpholin-4-yl


 40.
O
C6H5


 41.
O
2-F—C6H4


 42.
O
3-F—C6H4


 43.
O
4-F—C6H4


 44.
O
2-Cl—C6H4


 45.
O
3-Cl—C6H4


 46.
O
4-Cl—C6H4


 47.
O
2-Br—C6H4


 48.
O
3-Br—C6H4


 49.
O
4-Br—C6H4


 50.
O
C(═O)CH3


 51.
O
C(═O)CH2CH3


 52.
O
C(═O)CH2OCH3


 53.
O
C(═O)(CH2)2CH3


 54.
O
C(═O)CH(CH3)2


 55.
O
C(═O)C6H5


 56.
O
C(═O)-2-F—C6H4


 57.
O
C(═O)-3-F—C6H4


 58.
O
C(═O)-4-F—C6H4


 59.
O
C(═O)-2-Cl—C6H4


 60.
O
C(═O)-3-Cl—C6H4


 61.
O
C(═O)-4-Cl—C6H4


 62.
O
C(═O)-2-Br—C6H4


 63.
O
C(═O)-3-Br—C6H4


 64.
O
C(═O)-4-Br—C6H4


 65.
O
C(═O)-2-pyridyl


 66.
O
C(═O)CF3


 67.
O
C(═O)CH2CF3


 68.
O
C(═O)CH2CCl3


 69.
O
C(═O)OCH2Cl3


 70.
O
C(═O)OH


 71.
O
C(═O)OCH3


 72.
O
C(═O)OCH2CH3


 73.
O
C(═O)OCH2CH2CH3


 74.
O
C(═O)OCH(CH3)2


 75.
O
C(═O)O(CH2)3CH3


 76.
O
C(═O)OCH2CH(CH3)2


 77.
O
C(═O)OC(CH3)3


 78.
O
C(═O)NH2


 79.
O
C(═O)NHCH3


 80.
O
C(═O)N(CH3)2


 81.
O
C(═O)NHCF3


 82.
O
C(═O)N(CF3)2


 83.
O
C(═O)NHCH2CH3


 84.
O
C(═O)N(CH2CH3)2


 85.
O
C(═O)N(CH3)CH2CH3


 86.
O
C(═O)NHCH2CF3


 87.
O
C(═O)N(CH2CF3)2


 88.
O
C(═O)N(CH3)CH2CF3


 89.
O
C(═O)NHCH2CH2CH3


 90.
O
C(═O)N(CH3)CH2CH2CH3


 91.
O
C(═O)NHCH(CH3)2


 92.
O
C(═O)NH(CH2)3CH3


 93.
O
C(═O)N(CH3)—(CH2)3CH3


 94.
O
C(═O)N[(CH2)3CH3]2


 95.
O
C(═O)N(CH3)—CH2—C6H5


 96.
O
C(═O)NH-propargyl


 97.
O
C(═O)N(CH3)-propargyl


 98.
O
C(═O)NH—CH2-4-Cl—C6H4


 99.
O
C(═O)N(CH3)—CH2-4-Cl—C6H4


 100.
O
C(═O)morpholin-4-yl


 101.
O
C(═O)NH-3-thiolyl-1,1-dioxid


 102.
O
C(═O)N(CH3)-3-thiolyl-1,1-dioxid


 103.
O
C(═O)-azirid-1-yl


 104.
O
C(═O)-pyrrolidin-1-yl


 105.
O
C(═O)-piperidin-1-yl


 106.
O
C(═O)-thiomorpholin-4-yl


 107.
O
C(═O)NH—CH2CHF2


 108.
O
C(═O)NH—CH2CH2CHF2


 109.
O
C(═O)NH—CH2CH2CF3


 110.
O
C(═O)NH-cyclopropyl


 111.
O
C(═O)NH-cyclobutyl


 112.
O
C(═O)NH-cyclopentyl


 113.
O
C(═O)NH-cyclohexyl


 114.
O
C(═O)NH—CH2-cyclopropyl


 115.
O
C(═O)NH—CH2-cyclobutyl


 116.
O
C(═O)NH—CH2-cyclopentyl


 117.
O
C(═O)NH—CH2-cyclohexyl


 118.
O
C(═O)NH—CN


 119.
O
C(═O)NH—CH2—CN


 120.
O
C(═O)NH—CH2—CH═CH2


 121.
O
C(═O)NH—CH2—CH═C(Cl)2


 122.
O
C(═O)NH—CH2—CH═CH-phenyl


 123.
O
C(═O)NH—CH2—CH═CH-(4-Cl-phenyl)


 124.
O
C(═O)NH—CH2—SCH3


 125.
O
C(═O)NH—CH2—SCF3


 126.
O
C(═O)NH—CH2—CH2—SCH3


 127.
O
C(═O)NH—CH2—CH2—SCF3


 128.
O
C(═O)NH—CH2—SO2—CH3


 129.
O
C(═O)NH—CH2—SO2—CF3


 130.
O
C(═O)NH—CH2—CH2—SO2—CH3


 131.
O
C(═O)NH—CH2—CH2—SO2—CF3


 132.
O
C(═O)NH—CH2—CO—NH2


 133.
O
C(═O)NH—CH2—CO—NHCH3


 134.
O
C(═O)NH—CH2—CO—N(CH3)2


 135.
O
C(═O)NH—CH2—CO—NHCF3


 136.
O
C(═O)NH—CH2—CO—N(CF3)2


 137.
O
C(═O)NH—CH2—CO—NHCH2CH3


 138.
O
C(═O)NH—CH2—CO—N(CH2CH3)2


 139.
O
C(═O)NH—CH2—CO—NHCH2CF3


 140.
O
C(═O)NH—CH2—CO—N(CH2CF3)2


 141.
O
C(═O)NH—CH2—CO—NHCH2CH2CH3


 142.
O
C(═O)NH—CH2—CO—N(CH2CH2CH3)2


 143.
O
C(═O)NH—CH2—CO—NHCH2CH2CF3


 144.
O
C(═O)NH—CH2—CO—N(CH2CH2CF3)2


 145.
O
C(═O)NH—CH2—CO—NHCH(CH3)2


 146.
O
C(═O)NH—CH2—CO—NHCH(CF3)2


 147.
O
C(═O)NH—CH2—CO—NH-cyclopropyl


 148.
O
C(═O)NH—CH2—CO—NH—CH2-cyclopropyl


 149.
O
C(═O)NH—CH2—CO—OH


 150.
O
C(═O)NH—CH2—CO—OCH3


 151.
O
C(═O)NH—CH2—CO—OCF3


 152.
O
C(═O)NH—CH2—CO—OCH2CH3


 153.
O
C(═O)NH—CH2—CO—OCH2CF3


 154.
O
C(═O)NH—CH2—CO—OCH2CH2CH3


 155.
O
C(═O)NH—CH2—CO—OCH(CH3)2


 156.
O
C(═O)NH—CH2—CO—OCH2CH2CH2CH3


 157.
O
C(═O)NH—CH2—CO—OCH(CH3)CH2CH3


 158.
O
C(═O)NH—CH2—CO—OCH2CH(CH3)2


 159.
O
C(═O)NH—CH2—CO—OC(CH3)3


 160.
O
C(═O)NH-A-1


 161.
O
C(═O)NH-A-2


 162.
O
C(═O)NH-A-3


 163.
O
C(═O)NH-A-4


 164.
O
C(═O)NH-A-5


 165.
O
C(═O)NH-A-6


 166.
O
C(═O)NH-A-7


 167.
O
C(═O)NH-A-8


 168.
O
C(═O)NH-A-9


 169.
O
C(═O)NH-A-10


 170.
O
C(═O)NH-A-11


 171.
O
C(═O)NH-A-12


 172.
O
C(═O)NH-A-13


 173.
O
C(═O)NH-A-14


 174.
O
C(═O)NH-A-15


 175.
O
C(═O)NH-A-16


 176.
O
C(═O)NH-A-17


 177.
O
C(═O)NH-A-18


 178.
O
C(═O)NH-A-19


 179.
O
C(═O)NH-A-20


 180.
O
C(═O)NH-A-21


 181.
O
C(═O)NH-A-22


 182.
O
C(═O)NH-A-23


 183.
O
C(═O)NH-A-24


 184.
O
C(═O)NH-A-25


 185.
O
C(═O)NH-A-26


 186.
O
C(═O)NH-A-27


 187.
O
C(═O)NH-A-28


 188.
O
C(═O)NH-A-29


 189.
O
C(═O)NH-A-30


 190.
O
C(═O)NH-A-31


 191.
O
C(═O)NH-A-32


 192.
O
C(═O)NH-A-33


 193.
O
C(═O)NH—CH2-A-1


 194.
O
C(═O)NH—CH2-A-2


 195.
O
C(═O)NH—CH2-A-3


 196.
O
C(═O)NH—CH2-A-4


 197.
O
C(═O)NH—CH2-A-5


 198.
O
C(═O)NH—CH2-A-6


 199.
O
C(═O)NH—CH2-A-7


 200.
O
C(═O)NH—CH2-A-8


 201.
O
C(═O)NH—CH2-A-9


 202.
O
C(═O)NH—CH2-A-10


 203.
O
C(═O)NH—CH2-A-11


 204.
O
C(═O)NH—CH2-A-12


 205.
O
C(═O)NH—CH2-A-13


 206.
O
C(═O)NH—CH2-A-14


 207.
O
C(═O)NH—CH2-A-15


 208.
O
C(═O)NH—CH2-A-16


 209.
O
C(═O)NH—CH2-A-17


 210.
O
C(═O)NH—CH2-A-18


 211.
O
C(═O)NH—CH2-A-19


 212.
O
C(═O)NH—CH2-A-20


 213.
O
C(═O)NH—CH2-A-21


 214.
O
C(═O)NH—CH2-A-22


 215.
O
C(═O)NH—CH2-A-23


 216.
O
C(═O)NH—CH2-A-24


 217.
O
C(═O)NH—CH2-A-25


 218.
O
C(═O)NH—CH2-A-26


 219.
O
C(═O)NH—CH2-A-27


 220.
O
C(═O)NH—CH2-A-28


 221.
O
C(═O)NH—CH2-A-29


 222.
O
C(═O)NH—CH2-A-30


 223.
O
C(═O)NH—CH2-A-31


 224.
O
C(═O)NH—CH2-A-32


 225.
O
C(═O)NH—CH2-A-33


 226.
O
C(═O)NH—SO2—CH3


 227.
O
C(═O)NH—SO2—CF3


 228.
O
C(═O)NH—SO2—CH2CH3


 229.
O
C(═O)NH—SO2—CH2CF3


 230.
O
C(═O)NH—SO2—CH2CH2CH3


 231.
O
C(═O)NH—SO2—CH2CH2CF3


 232.
O
C(═O)NH—SO2—CH2CF2CF3


 233.
O
C(═O)NH—SO2—CH(CH3)2


 234.
O
C(═O)NH—SO2—CH(CF3)2


 235.
O
C(═O)N(CH3)—CH2CHF2


 236.
O
C(═O)N(CH3)—CH2CH2CHF2


 237.
O
C(═O)N(CH3)—CH2CH2CF3


 238.
O
C(═O)N(CH3)-cyclopropyl


 239.
O
C(═O)N(CH3)-cyclobutyl


 240.
O
C(═O)N(CH3)-cyclopentyl


 241.
O
C(═O)N(CH3)-cyclohexyl


 242.
O
C(═O)N(CH3)—CH2-cyclopropyl


 243.
O
C(═O)N(CH3)—CH2-cyclobutyl


 244.
O
C(═O)N(CH3)—CH2-cyclopentyl


 245.
O
C(═O)N(CH3)—CH2-cyclohexyl


 246.
O
C(═O)N(CH3)—CN


 247.
O
C(═O)N(CH3)—CH2—CN


 248.
O
C(═O)N(CH3)—CH2—CH═CH2


 249.
O
C(═O)N(CH3)—CH2—CH═C(Cl)2


 250.
O
C(═O)N(CH3)—CH2—CH═CH-phenyl


 251.
O
C(═O)N(CH3)—CH2—CH═CH-(4-Cl-phenyl)


 252.
O
C(═O)N(CH3)—CH2—SCH3


 253.
O
C(═O)N(CH3)—CH2—SCF3


 254.
O
C(═O)N(CH3)—CH2—CH2—SCH3


 255.
O
C(═O)N(CH3)—CH2—CH2—SCF3


 256.
O
C(═O)N(CH3)—CH2—SO2—CH3


 257.
O
C(═O)N(CH3)—CH2—SO2—CF3


 258.
O
C(═O)N(CH3)—CH2—CH2—SO2—CH3


 259.
O
C(═O)N(CH3)—CH2—CH2—SO2—CF3


 260.
O
C(═O)N(CH3)—CH2—CO—NH2


 261.
O
C(═O)N(CH3)—CH2—CO—NHCH3


 262.
O
C(═O)N(CH3)—CH2—CO—N(CH3)2


 263.
O
C(═O)N(CH3)—CH2—CO—NHCF3


 264.
O
C(═O)N(CH3)—CH2—CO—N(CF3)2


 265.
O
C(═O)N(CH3)—CH2—CO—NHCH2CH3


 266.
O
C(═O)N(CH3)—CH2—CO—N(CH2CH3)2


 267.
O
C(═O)N(CH3)—CH2—CO—NHCH2CF3


 268.
O
C(═O)N(CH3)—CH2—CO—N(CH2CF3)2


 269.
O
C(═O)N(CH3)—CH2—CO—NHCH2CH2CH3


 270.
O
C(═O)N(CH3)—CH2—CO—N(CH2CH2CH3)2


 271.
O
C(═O)N(CH3)—CH2—CO—NHCH2CH2CF3


 272.
O
C(═O)N(CH3)—CH2—CO—N(CH2CH2CF3)2


 273.
O
C(═O)N(CH3)—CH2—CO—NHCH(CH3)2


 274.
O
C(═O)N(CH3)—CH2—CO—NHCH(CF3)2


 275.
O
C(═O)N(CH3)—CH2—CO—NH-cyclopropyl


 276.
O
C(═O)N(CH3)—CH2—CO—NH—CH2-cyclopropyl


 277.
O
C(═O)N(CH3)—CH2—CO—OH


 278.
O
C(═O)N(CH3)—CH2—CO—OCH3


 279.
O
C(═O)N(CH3)—CH2—CO—OCF3


 280.
O
C(═O)N(CH3)—CH2—CO—OCH2CH3


 281.
O
C(═O)N(CH3)—CH2—CO—OCH2CF3


 282.
O
C(═O)N(CH3)—CH2—CO—OCH2CH2CH3


 283.
O
C(═O)N(CH3)—CH2—CO—OCH(CH3)2


 284.
O
C(═O)N(CH3)—CH2—CO—OCH2CH2CH2CH3


 285.
O
C(═O)N(CH3)—CH2—CO—OCH(CH3)CH2CH3


 286.
O
C(═O)N(CH3)—CH2—CO—OCH2CH(CH3)2


 287.
O
C(═O)N(CH3)—CH2—CO—OC(CH3)3


 288.
O
C(═O)N(CH3)-A-1


 289.
O
C(═O)N(CH3)-A-2


 290.
O
C(═O)N(CH3)-A-3


 291.
O
C(═O)N(CH3)-A-4


 292.
O
C(═O)N(CH3)-A-5


 293.
O
C(═O)N(CH3)-A-6


 294.
O
C(═O)N(CH3)-A-7


 295.
O
C(═O)N(CH3)-A-8


 296.
O
C(═O)N(CH3)-A-9


 297.
O
C(═O)N(CH3)-A-10


 298.
O
C(═O)N(CH3)-A-11


 299.
O
C(═O)N(CH3)-A-12


 300.
O
C(═O)N(CH3)-A-13


 301.
O
C(═O)N(CH3)-A-14


 302.
O
C(═O)N(CH3)-A-15


 303.
O
C(═O)N(CH3)-A-16


 304.
O
C(═O)N(CH3)-A-17


 305.
O
C(═O)N(CH3)-A-18


 306.
O
C(═O)N(CH3)-A-19


 307.
O
C(═O)N(CH3)-A-20


 308.
O
C(═O)N(CH3)-A-21


 309.
O
C(═O)N(CH3)-A-22


 310.
O
C(═O)N(CH3)-A-23


 311.
O
C(═O)N(CH3)-A-24


 312.
O
C(═O)N(CH3)-A-25


 313.
O
C(═O)N(CH3)-A-26


 314.
O
C(═O)N(CH3)-A-27


 315.
O
C(═O)N(CH3)-A-28


 316.
O
C(═O)N(CH3)-A-29


 317.
O
C(═O)N(CH3)-A-30


 318.
O
C(═O)N(CH3)-A-31


 319.
O
C(═O)N(CH3)-A-32


 320.
O
C(═O)N(CH3)-A-33


 321.
O
C(═O)N(CH3)—CH2-A-1


 322.
O
C(═O)N(CH3)—CH2-A-2


 323.
O
C(═O)N(CH3)—CH2-A-3


 324.
O
C(═O)N(CH3)—CH2-A-4


 325.
O
C(═O)N(CH3)—CH2-A-5


 326.
O
C(═O)N(CH3)—CH2-A-6


 327.
O
C(═O)N(CH3)—CH2-A-7


 328.
O
C(═O)N(CH3)—CH2-A-8


 329.
O
C(═O)N(CH3)—CH2-A-9


 330.
O
C(═O)N(CH3)—CH2-A-10


 331.
O
C(═O)N(CH3)—CH2-A-11


 332.
O
C(═O)N(CH3)—CH2-A-12


 333.
O
C(═O)N(CH3)—CH2-A-13


 334.
O
C(═O)N(CH3)—CH2-A-14


 335.
O
C(═O)N(CH3)—CH2-A-15


 336.
O
C(═O)N(CH3)—CH2-A-16


 337.
O
C(═O)N(CH3)—CH2-A-17


 338.
O
C(═O)N(CH3)—CH2-A-18


 339.
O
C(═O)N(CH3)—CH2-A-19


 340.
O
C(═O)N(CH3)—CH2-A-20


 341.
O
C(═O)N(CH3)—CH2-A-21


 342.
O
C(═O)N(CH3)—CH2-A-22


 343.
O
C(═O)N(CH3)—CH2-A-23


 344.
O
C(═O)N(CH3)—CH2-A-24


 345.
O
C(═O)N(CH3)—CH2-A-25


 346.
O
C(═O)N(CH3)—CH2-A-26


 347.
O
C(═O)N(CH3)—CH2-A-27


 348.
O
C(═O)N(CH3)—CH2-A-28


 349.
O
C(═O)N(CH3)—CH2-A-29


 350.
O
C(═O)N(CH3)—CH2-A-30


 351.
O
C(═O)N(CH3)—CH2-A-31


 352.
O
C(═O)N(CH3)—CH2-A-32


 353.
O
C(═O)N(CH3)—CH2-A-33


 354.
O
C(═O)N(CH3)—SO2—CH3


 355.
O
C(═O)N(CH3)—SO2—CF3


 356.
O
C(═O)N(CH3)—SO2—CH2CH3


 357.
O
C(═O)N(CH3)—SO2—CH2CF3


 358.
O
C(═O)N(CH3)—SO2—CH2CH2CH3


 359.
O
C(═O)N(CH3)—SO2—CH2CH2CF3


 360.
O
C(═O)N(CH3)—SO2—CH2CF2CF3


 361.
O
C(═O)N(CH3)—SO2—CH(CH3)2


 362.
O
C(═O)N(CH3)—SO2—CH(CF3)2


 363.
O
C(═O)NH—SO2—NH2


 364.
O
C(═O)NH—SO2—NHCH3


 365.
O
C(═O)NH—SO2—N(CH3)2


 366.
O
C(═O)NH—SO2—NHCF3


 367.
O
C(═O)NH—SO2—N(CF3)2


 368.
O
C(═O)NH—SO2—NHCH2CH3


 369.
O
C(═O)NH—SO2—N(CH2CH3)2


 370.
O
C(═O)NH—SO2—NHCH2CF3


 371.
O
C(═O)NH—SO2—N(CH2CF3)2


 372.
O
C(═O)NH—SO2—N(CH3)CH2CH3


 373.
O
C(═O)NH—SO2—N(CH3)CH2CF3


 374.
O
C(═O)NH—SO2—N(CF3)CH2CH3


 375.
O
C(═O)NH—SO2—NHCH2CH2CH3


 376.
O
C(═O)NH—SO2—N(CH2CH2CH3)2


 377.
O
C(═O)NH—SO2—NHCH2CH2CF3


 378.
O
C(═O)NH—SO2—N(CH2CH2CF3)2


 379.
O
C(═O)NH—SO2—N(CH3)CH2CH2CH3


 380.
O
C(═O)NH—SO2—N(CH3)CH2CH2CF3


 381.
O
C(═O)NH—SO2—N(CF3)CH2CH2CH3


 382.
O
C(═O)NH—SO2—NHCH(CH3)2


 383.
O
C(═O)NH—SO2—NHCH(CF3)2


 384.
O
C(═O)NH—SO2—N(CH3)CH(CH3)2


 385.
O
C(═O)NH—SO2—N(CH3)CH(CF3)2


 386.
O
C(═O)NH—SO2—N(CF3)CH(CH3)2


 387.
O
C(═O)NH—SO2—NHCH2CH2CH2CH3


 388.
O
C(═O)NH—SO2—N(CH2CH2CH2CH3)2


 389.
O
C(═O)NH—SO2—N(CH3)CH2CH2CH2CH3


 390.
O
C(═O)N(CH3)—SO2—NH2


 391.
O
C(═O)N(CH3)—SO2—NHCH3


 392.
O
C(═O)N(CH3)—SO2—N(CH3)2


 393.
O
C(═O)N(CH3)—SO2—NHCF3


 394.
O
C(═O)N(CH3)—SO2—N(CF3)2


 395.
O
C(═O)N(CH3)—SO2—NHCH2CH3


 396.
O
C(═O)N(CH3)—SO2—N(CH2CH3)2


 397.
O
C(═O)N(CH3)—SO2—NHCH2CF3


 398.
O
C(═O)N(CH3)—SO2—N(CH2CF3)2


 399.
O
C(═O)N(CH3)—SO2—N(CH3)CH2CH3


 400.
O
C(═O)N(CH3)—SO2—N(CH3)CH2CF3


 401.
O
C(═O)N(CH3)—SO2—N(CF3)CH2CH3


 402.
O
C(═O)N(CH3)—SO2—NHCH2CH2CH3


 403.
O
C(═O)N(CH3)—SO2—N(CH2CH2CH3)2


 404.
O
C(═O)N(CH3)—SO2—NHCH2CH2CF3


 405.
O
C(═O)N(CH3)—SO2—N(CH2CH2CF3)2


 406.
O
C(═O)N(CH3)—SO2—N(CH3)CH2CH2CH3


 407.
O
C(═O)N(CH3)—SO2—N(CH3)CH2CH2CF3


 408.
O
C(═O)N(CH3)—SO2—N(CF3)CH2CH2CH3


 409.
O
C(═O)N(CH3)—SO2—NHCH(CH3)2


 410.
O
C(═O)N(CH3)—SO2—NHCH(CF3)2


 411.
O
C(═O)N(CH3)—SO2—N(CH3)CH(CH3)2


 412.
O
C(═O)N(CH3)—SO2—N(CH3)CH(CF3)2


 413.
O
C(═O)N(CH3)—SO2—N(CF3)CH(CH3)2


 414.
O
C(═O)N(CH3)—SO2—NHCH2CH2CH2CH3


 415.
O
C(═O)N(CH3)—SO2—N(CH2CH2CH2CH3)2


 416.
O
C(═O)N(CH3)—SO2—N(CH3)CH2CH2CH2CH3


 417.
O
C(═O)—N═CHOCH3


 418.
O
C(═O)—N═CHOCH2CH3


 419.
O
C(═O)—N═CHOCH2CH2CH3


 420.
O
C(═O)—N═CHOCH(CH3)2


 421.
O
C(═O)—N═CHOCF3


 422.
O
C(═O)—N═CHOCH2CF3


 423.
O
C(═O)—N═CHOCH2CH2CF3


 424.
O
C(═O)—N═CHOCH(CF3)2


 425.
O
C(═O)—N═CH—CO—OCH3


 426.
O
C(═O)—N═CH—CO—OCH2CH3


 427.
O
C(═O)—N═CH—CO—OCH2CH2CH3


 428.
O
C(═O)—N═CH—CO—OCH(CH3)2


 429.
O
C(═O)—N═CH—CO—OCF3


 430.
O
C(═O)—N═CH—CO—OCH2CF3


 431.
O
C(═O)—N═CH—CO—OCH2CH2CF3


 432.
O
C(═O)—N═CH—CO—OCH(CF3)2


 433.
O
C(═O)—N═CH—CO—NHCH3


 434.
O
C(═O)—N═CH—CO—N(CH3)2


 435.
O
C(═O)—N═CH—CO—NHCH2CH3


 436.
O
C(═O)—N═CH—CO—N(CH2CH3)2


 437.
O
C(═O)—N═CH—CO—N(CH3)CH2CH3


 438.
O
C(═O)—N═CH—CO—NHCH2CH2CH3


 439.
O
C(═O)—N═CH—CO—N(CH2CH2CH3)2


 440.
O
C(═O)—N═CH—CO—N(CH3)CH2CH2CH3


 441.
O
C(═O)—N═CH—CO—NHCH(CH3)2


 442.
O
C(═O)—N═CH—CO—N(CH3)CH(CH3)2


 443.
O
C(═O)—N═CH—CO—NHCF3


 444.
O
C(═O)—N═CH—CO—N(CF3)2


 445.
O
C(═O)—N═CH—CO—NHCH2CF3


 446.
O
C(═O)—N═CH—CO—N(CH2CF3)2


 447.
O
C(═O)—N═CH—CO—N(CH3)CH2CF3


 448.
O
C(═O)—N═CH—CO—N(CF3)CH2CF3


 449.
O
C(═O)—N═CH—CO—NHCH2CH2CF3


 450.
O
C(═O)—N═CH—CO—N(CH2CH2CF3)2


 451.
O
C(═O)—N═CH—CO—N(CH3)CH2CH2CF3


 452.
O
C(═O)—N═CH—CO—N(CF3)CH2CH2CH3


 453.
O
C(═O)—N═CH—CO—NHCH(CF3)2


 454.
O
C(═O)—N═CH—CO—N(CH3)CH(CF3)2


 455.
O
C(═O)—N═CH—CO—N(CF3)CH(CH3)2


 456.
O
C(═NH)NH2


 457.
O
C(═NH)NHCH3


 458.
O
C(═NH)N(CH3)2


 459.
O
C(═NH)NHCF3


 460.
O
C(═NH)N(CF3)2


 461.
O
C(═NH)NHCH2CH3


 462.
O
C(═NH)N(CH2CH3)2


 463.
O
C(═NH)NHCH2CF3


 464.
O
C(═NH)N(CH2CF3)2


 465.
O
C(═NH)NHCH2CH2CH3


 466.
O
C(═NH)NHCH(CH3)2


 467.
O
C(═NH)NH(CH2)3CH3


 468.
O
C(═NH)NH(CH2)4CH3


 469.
O
C(═NH)NH(CH2)5CH3


 470.
O
C(═NH)NHCH2-cpropyl


 471.
O
C(═NH)NHCH2—C6H5


 472.
O
C(═NCH3)NH2


 473.
O
C(═NCH3)NHCH3


 474.
O
C(═NCH3)N(CH3)2


 475.
O
C(═NCH3)NHCF3


 476.
O
C(═NCH3)N(CF3)2


 477.
O
C(═NCH3)NHCH2CH3


 478.
O
C(═NCH3)N(CH2CH3)2


 479.
O
C(═NCH3)NHCH2CF3


 480.
O
C(═NCH3)N(CH2CF3)2


 481.
O
C(═NCH3)NHCH2CH2CH3


 482.
O
C(═NCH3)NHCH(CH3)2


 483.
O
C(═NCH3)NH(CH2)3CH3


 484.
O
C(═NCH3)NH(CH2)4CH3


 485.
O
C(═NCH3)NH(CH2)5CH3


 486.
O
C(═NCH3)NHCH2-cpropyl


 487.
O
C(═NCH3)NHCH2—C6H5


 488.
O
CH2C6H5


 489.
O
CH2CH2C6H5


 490.
O
CH2-2-F—C6H4


 491.
O
CH2-3-F—C6H4


 492.
O
CH2-4-F—C6H4


 493.
O
CH2-2-Cl—C6H4


 494.
O
CH2-3-Cl—C6H4


 495.
O
CH2-4-Cl—C6H4


 496.
O
CH2-2-Br—C6H4


 497.
O
CH2-3-Br—C6H4


 498.
O
CH2-4-Br—C6H4


 499.
O
CH2-2-MeO—C6H4


 500.
O
CH2-3-MeO—C6H4


 501.
O
CH2-4-MeO—C6H4


 502.
O
CH2-2-F—C6H4


 503.
O
CH2-3-F—C6H4


 504.
O
CH2-4-F—C6H4


 505.
O
A-1


 506.
O
A-2


 507.
O
A-3


 508.
O
A-4


 509.
O
A-5


 510.
O
A-6


 511.
O
A-7


 512.
O
A-8


 513.
O
A-9


 514.
O
A-10


 515.
O
A-11


 516.
O
A-12


 517.
O
A-13


 518.
O
A-14


 519.
O
A-15


 520.
O
A-16


 521.
O
A-17


 522.
O
A-18


 523.
O
A-19


 524.
O
A-20


 525.
O
A-21


 526.
O
A-22


 527.
O
A-23


 528.
O
A-24


 529.
O
A-25


 530.
O
A-26


 531.
O
A-27


 532.
O
A-28


 533.
O
A-29


 534.
O
A-30


 535.
O
A-31


 536.
O
A-32


 537.
O
A-33


 538.
O
CH2-A-1


 539.
O
CH2-A-2


 540.
O
CH2-A-3


 541.
O
CH2-A-4


 542.
O
CH2-A-5


 543.
O
CH2-A-6


 544.
O
CH2-A-7


 545.
O
CH2-A-8


 546.
O
CH2-A-9


 547.
O
CH2-A-10


 548.
O
CH2-A-11


 549.
O
CH2-A-12


 550.
O
CH2-A-13


 551.
O
CH2-A-14


 552.
O
CH2-A-15


 553.
O
CH2-A-16


 554.
O
CH2-A-17


 555.
O
CH2-A-18


 556.
O
CH2-A-19


 557.
O
CH2-A-20


 558.
O
CH2-A-21


 559.
O
CH2-A-22


 560.
O
CH2-A-23


 561.
O
CH2-A-24


 562.
O
CH2-A-25


 563.
O
CH2-A-26


 564.
O
CH2-A-27


 565.
O
CH2-A-28


 566.
O
CH2-A-29


 567.
O
CH2-A-30


 568.
O
CH2-A-31


 569.
O
CH2-A-32


 570.
O
CH2-A-33


 571.
O
C(═O)-A-1


 572.
O
C(═O)-A-2


 573.
O
C(═O)-A-3


 574.
O
C(═O)-A-4


 575.
O
C(═O)-A-5


 576.
O
C(═O)-A-6


 577.
O
C(═O)-A-7


 578.
O
C(═O)-A-8


 579.
O
C(═O)-A-9


 580.
O
C(═O)-A-10


 581.
O
C(═O)-A-11


 582.
O
C(═O)-A-12


 583.
O
C(═O)-A-13


 584.
O
C(═O)-A-14


 585.
O
C(═O)-A-15


 586.
O
C(═O)-A-16


 587.
O
C(═O)-A-17


 588.
O
C(═O)-A-18


 589.
O
C(═O)-A-19


 590.
O
C(═O)-A-20


 591.
O
C(═O)-A-21


 592.
O
C(═O)-A-22


 593.
O
C(═O)-A-23


 594.
O
C(═O)-A-24


 595.
O
C(═O)-A-25


 596.
O
C(═O)-A-26


 597.
O
C(═O)-A-27


 598.
O
C(═O)-A-28


 599.
O
C(═O)-A-29


 600.
O
C(═O)-A-30


 601.
O
C(═O)-A-31


 602.
O
C(═O)-A-32


 603.
O
C(═O)-A-33


 604.
NH
C(═O)NH2


 605.
NH
C(═O)NHCH3


 606.
NH
C(═O)N(CH3)2


 607.
NH
C(═O)NHCF3


 608.
NH
C(═O)N(CF3)2


 609.
NH
C(═O)NHCH2CH3


 610.
NH
C(═O)N(CH2CH3)2


 611.
NH
C(═O)(CH3)CH2CH3


 612.
NH
C(═O)NHCH2CF3


 613.
NH
C(═O)N(CH2CF3)2


 614.
NH
C(═O)N(CH3)CH2CF3


 615.
NH
C(═O)NHCH2CH2CH3


 616.
NH
C(═O)N(CH3)CH2CH2CH3


 617.
NH
C(═O)NHCH(CH3)2


 618.
NH
C(═O)NH(CH2)3CH3


 619.
NH
C(═O)N(CH3)—(CH2)3CH3


 620.
NH
C(═O)N[(CH2)3CH3]2


 621.
NH
C(═O)N(CH3)—CH2—C6H5


 622.
NH
C(═O)NH-propargyl


 623.
NH
C(═O)N(CH3)-propargyl


 624.
NH
C(═O)NH—CH2-4-Cl—C6H4


 625.
NH
C(═O)N(CH3)—CH2-4-Cl—C6H4


 626.
NH
C(═O)morpholin-4-yl


 627.
NH
C(═O)NH-3-thiolyl-1,1-dioxid


 628.
NH
C(═O)N(CH3)-3-thiolyl-1,1-dioxid


 629.
NH
C(═O)-azirid-1-yl


 630.
NH
C(═O)-pyrrolidin-1-yl


 631.
NH
C(═O)-piperidin-1-yl


 632.
NH
C(═O)-thiomorpholin-4-yl


 633.
NH
C(═O)NH—CH2CHF2


 634.
NH
C(═O)NH—CH2CH2CHF2


 635.
NH
C(═O)NH—CH2CH2CF3


 636.
NH
C(═O)NH-cyclopropyl


 637.
NH
C(═O)NH-cyclobutyl


 638.
NH
C(═O)NH-cyclopentyl


 639.
NH
C(═O)NH-cyclohexyl


 640.
NH
C(═O)NH—CH2-cyclopropyl


 641.
NH
C(═O)NH—CH2-cyclobutyl


 642.
NH
C(═O)NH—CH2-cyclopentyl


 643.
NH
C(═O)NH—CH2-cyclohexyl


 644.
NH
C(═O)NH—CN


 645.
NH
C(═O)NH—CH2—CN


 646.
NH
C(═O)NH—CH2—CH═CH2


 647.
NH
C(═O)NH—CH2—CH═C(Cl)2


 648.
NH
C(═O)NH—CH2—CH═CH-phenyl


 649.
NH
C(═O)NH—CH2—CH═CH-(4-Cl-phenyl)


 650.
NH
C(═O)NH—CH2—SCH3


 651.
NH
C(═O)NH—CH2—SCF3


 652.
NH
C(═O)NH—CH2—CH2—SCH3


 653.
NH
C(═O)NH—CH2—CH2—SCF3


 654.
NH
C(═O)NH—CH2—SO2—CH3


 655.
NH
C(═O)NH—CH2—SO2—CF3


 656.
NH
C(═O)NH—CH2—CH2—SO2—CH3


 657.
NH
C(═O)NH—CH2—CH2—SO2—CF3


 658.
NH
C(═O)NH—CH2—CO—NH2


 659.
NH
C(═O)NH—CH2—CO—NHCH3


 660.
NH
C(═O)NH—CH2—CO—N(CH3)2


 661.
NH
C(═O)NH—CH2—CO—NHCF3


 662.
NH
C(═O)NH—CH2—CO—N(CF3)2


 663.
NH
C(═O)NH—CH2—CO—NHCH2CH3


 664.
NH
C(═O)NH—CH2—CO—N(CH2CH3)2


 665.
NH
C(═O)NH—CH2—CO—NHCH2CF3


 666.
NH
C(═O)NH—CH2—CO—N(CH2CF3)2


 667.
NH
C(═O)NH—CH2—CO—NHCH2CH2CH3


 668.
NH
C(═O)NH—CH2—CO—N(CH2CH2CH3)2


 669.
NH
C(═O)NH—CH2—CO—NHCH2CH2CF3


 670.
NH
C(═O)NH—CH2—CO—N(CH2CH2CF3)2


 671.
NH
C(═O)NH—CH2—CO—NHCH(CH3)2


 672.
NH
C(═O)NH—CH2—CO—NHCH(CF3)2


 673.
NH
C(═O)NH—CH2—CO—NH-cyclopropyl


 674.
NH
C(═O)NH—CH2—CO—NH—CH2-cyclopropyl


 675.
NH
C(═O)NH—CH2—CO—OH


 676.
NH
C(═O)NH—CH2—CO—OCH3


 677.
NH
C(═O)NH—CH2—CO—OCF3


 678.
NH
C(═O)NH—CH2—CO—OCH2CH3


 679.
NH
C(═O)NH—CH2—CO—OCH2CF3


 680.
NH
C(═O)NH—CH2—CO—OCH2CH2CH3


 681.
NH
C(═O)NH—CH2—CO—OCH(CH3)2


 682.
NH
C(═O)NH—CH2—CO—OCH2CH2CH2CH3


 683.
NH
C(═O)NH—CH2—CO—OCH(CH3)CH2CH3


 684.
NH
C(═O)NH—CH2—CO—OCH2CH(CH3)2


 685.
NH
C(═O)NH—CH2—CO—OC(CH3)3


 686.
NH
C(═O)NH-A-1


 687.
NH
C(═O)NH-A-2


 688.
NH
C(═O)NH-A-3


 689.
NH
C(═O)NH-A-4


 690.
NH
C(═O)NH-A-5


 691.
NH
C(═O)NH-A-6


 692.
NH
C(═O)NH-A-7


 693.
NH
C(═O)NH-A-8


 694.
NH
C(═O)NH-A-9


 695.
NH
C(═O)NH-A-10


 696.
NH
C(═O)NH-A-11


 697.
NH
C(═O)NH-A-12


 698.
NH
C(═O)NH-A-13


 699.
NH
C(═O)NH-A-14


 700.
NH
C(═O)NH-A-15


 701.
NH
C(═O)NH-A-16


 702.
NH
C(═O)NH-A-17


 703.
NH
C(═O)NH-A-18


 704.
NH
C(═O)NH-A-19


 705.
NH
C(═O)NH-A-20


 706.
NH
C(═O)NH-A-21


 707.
NH
C(═O)NH-A-22


 708.
NH
C(═O)NH-A-23


 709.
NH
C(═O)NH-A-24


 710.
NH
C(═O)NH-A-25


 711.
NH
C(═O)NH-A-26


 712.
NH
C(═O)NH-A-27


 713.
NH
C(═O)NH-A-28


 714.
NH
C(═O)NH-A-29


 715.
NH
C(═O)NH-A-30


 716.
NH
C(═O)NH-A-31


 717.
NH
C(═O)NH-A-32


 718.
NH
C(═O)NH-A-33


 719.
NH
C(═O)NH—CH2-A-1


 720.
NH
C(═O)NH—CH2-A-2


 721.
NH
C(═O)NH—CH2-A-3


 722.
NH
C(═O)NH—CH2-A-4


 723.
NH
C(═O)NH—CH2-A-5


 724.
NH
C(═O)NH—CH2-A-6


 725.
NH
C(═O)NH—CH2-A-7


 726.
NH
C(═O)NH—CH2-A-8


 727.
NH
C(═O)NH—CH2-A-9


 728.
NH
C(═O)NH—CH2-A-10


 729.
NH
C(═O)NH—CH2-A-11


 730.
NH
C(═O)NH—CH2-A-12


 731.
NH
C(═O)NH—CH2-A-13


 732.
NH
C(═O)NH—CH2-A-14


 733.
NH
C(═O)NH—CH2-A-15


 734.
NH
C(═O)NH—CH2-A-16


 735.
NH
C(═O)NH—CH2-A-17


 736.
NH
C(═O)NH—CH2-A-18


 737.
NH
C(═O)NH—CH2-A-19


 738.
NH
C(═O)NH—CH2-A-20


 739.
NH
C(═O)NH—CH2-A-21


 740.
NH
C(═O)NH—CH2-A-22


 741.
NH
C(═O)NH—CH2-A-23


 742.
NH
C(═O)NH—CH2-A-24


 743.
NH
C(═O)NH—CH2-A-25


 744.
NH
C(═O)NH—CH2-A-26


 745.
NH
C(═O)NH—CH2-A-27


 746.
NH
C(═O)NH—CH2-A-28


 747.
NH
C(═O)NH—CH2-A-29


 748.
NH
C(═O)NH—CH2-A-30


 749.
NH
C(═O)NH—CH2-A-31


 750.
NH
C(═O)NH—CH2-A-32


 751.
NH
C(═O)NH—CH2-A-33


 752.
NH
C(═O)NH—SO2—CH3


 753.
NH
C(═O)NH—SO2—CF3


 754.
NH
C(═O)NH—SO2—CH2CH3


 755.
NH
C(═O)NH—SO2—CH2CF3


 756.
NH
C(═O)NH—SO2—CH2CH2CH3


 757.
NH
C(═O)NH—SO2—CH2CH2CF3


 758.
NH
C(═O)NH—SO2—CH2CF2CF3


 759.
NH
C(═O)NH—SO2—CH(CH3)2


 760.
NH
C(═O)NH—SO2—CH(CF3)2


 761.
NH
C(═O)N(CH3)—CH2CHF2


 762.
NH
C(═O)N(CH3)—CH2CH2CHF2


 763.
NH
C(═O)N(CH3)—CH2CH2CF3


 764.
NH
C(═O)N(CH3)-cyclopropyl


 765.
NH
C(═O)N(CH3)-cyclobutyl


 766.
NH
C(═O)N(CH3)-cyclopentyl


 767.
NH
C(═O)N(CH3)-cyclohexyl


 768.
NH
C(═O)N(CH3)—CH2-cyclopropyl


 769.
NH
C(═O)N(CH3)—CH2-cyclobutyl


 770.
NH
C(═O)N(CH3)—CH2-cyclopentyl


 771.
NH
C(═O)N(CH3)—CH2-cyclohexyl


 772.
NH
C(═O)N(CH3)—CN


 773.
NH
C(═O)N(CH3)—CH2—CN


 774.
NH
C(═O)N(CH3)—CH2—CH═CH2


 775.
NH
C(═O)N(CH3)—CH2—CH═C(Cl)2


 776.
NH
C(═O)N(CH3)—CH2—CH═CH-phenyl


 777.
NH
C(═O)N(CH3)—CH2—CH═CH-(4-Cl-phenyl)


 778.
NH
C(═O)N(CH3)—CH2—SCH3


 779.
NH
C(═O)N(CH3)—CH2—SCF3


 780.
NH
C(═O)N(CH3)—CH2—CH2—SCH3


 781.
NH
C(═O)N(CH3)—CH2—CH2—SCF3


 782.
NH
C(═O)N(CH3)—CH2—SO2—CH3


 783.
NH
C(═O)N(CH3)—CH2—SO2—CF3


 784.
NH
C(═O)N(CH3)—CH2—CH2—SO2—CH3


 785.
NH
C(═O)N(CH3)—CH2—CH2—SO2—CF3


 786.
NH
C(═O)N(CH3)—CH2—CO—NH2


 787.
NH
C(═O)N(CH3)—CH2—CO—NHCH3


 788.
NH
C(═O)N(CH3)—CH2—CO—N(CH3)2


 789.
NH
C(═O)N(CH3)—CH2—CO—NHCF3


 790.
NH
C(═O)N(CH3)—CH2—CO—N(CF3)2


 791.
NH
C(═O)N(CH3)—CH2—CO—NHCH2CH3


 792.
NH
C(═O)N(CH3)—CH2—CO—N(CH2CH3)2


 793.
NH
C(═O)N(CH3)—CH2—CO—NHCH2CF3


 794.
NH
C(═O)N(CH3)—CH2—CO—N(CH2CF3)2


 795.
NH
C(═O)N(CH3)—CH2—CO—NHCH2CH2CH3


 796.
NH
C(═O)N(CH3)—CH2—CO—N(CH2CH2CH3)2


 797.
NH
C(═O)N(CH3)—CH2—CO—NHCH2CH2CF3


 798.
NH
C(═O)N(CH3)—CH2—CO—N(CH2CH2CF3)2


 799.
NH
C(═O)N(CH3)—CH2—CO—NHCH(CH3)2


 800.
NH
C(═O)N(CH3)—CH2—CO—NHCH(CF3)2


 801.
NH
C(═O)N(CH3)—CH2—CO—NH-cyclopropyl


 802.
NH
C(═O)N(CH3)—CH2—CO—NH—CH2-cyclopropyl


 803.
NH
C(═O)N(CH3)—CH2—CO—OH


 804.
NH
C(═O)N(CH3)—CH2—CO—OCH3


 805.
NH
C(═O)N(CH3)—CH2—CO—OCF3


 806.
NH
C(═O)N(CH3)—CH2—CO—OCH2CH3


 807.
NH
C(═O)N(CH3)—CH2—CO—OCH2CF3


 808.
NH
C(═O)N(CH3)—CH2—CO—OCH2CH2CH3


 809.
NH
C(═O)N(CH3)—CH2—CO—OCH(CH3)2


 810.
NH
C(═O)N(CH3)—CH2—CO—OCH2CH2CH2CH3


 811.
NH
C(═O)N(CH3)—CH2—CO—OCH(CH3)CH2CH3


 812.
NH
C(═O)N(CH3)—CH2—CO—OCH2CH(CH3)2


 813.
NH
C(═O)N(CH3)—CH2—CO—OC(CH3)3


 814.
NH
C(═O)N(CH3)-A-1


 815.
NH
C(═O)N(CH3)-A-2


 816.
NH
C(═O)N(CH3)-A-3


 817.
NH
C(═O)N(CH3)-A-4


 818.
NH
C(═O)N(CH3)-A-5


 819.
NH
C(═O)N(CH3)-A-6


 820.
NH
C(═O)N(CH3)-A-7


 821.
NH
C(═O)N(CH3)-A-8


 822.
NH
C(═O)N(CH3)-A-9


 823.
NH
C(═O)N(CH3)-A-10


 824.
NH
C(═O)N(CH3)-A-11


 825.
NH
C(═O)N(CH3)-A-12


 826.
NH
C(═O)N(CH3)-A-13


 827.
NH
C(═O)N(CH3)-A-14


 828.
NH
C(═O)N(CH3)-A-15


 829.
NH
C(═O)N(CH3)-A-16


 830.
NH
C(═O)N(CH3)-A-17


 831.
NH
C(═O)N(CH3)-A-18


 832.
NH
C(═O)N(CH3)-A-19


 833.
NH
C(═O)N(CH3)-A-20


 834.
NH
C(═O)N(CH3)-A-21


 835.
NH
C(═O)N(CH3)-A-22


 836.
NH
C(═O)N(CH3)-A-23


 837.
NH
C(═O)N(CH3)-A-24


 838.
NH
C(═O)N(CH3)-A-25


 839.
NH
C(═O)N(CH3)-A-26


 840.
NH
C(═O)N(CH3)-A-27


 841.
NH
C(═O)N(CH3)-A-28


 842.
NH
C(═O)N(CH3)-A-29


 843.
NH
C(═O)N(CH3)-A-30


 844.
NH
C(═O)N(CH3)-A-31


 845.
NH
C(═O)N(CH3)-A-32


 846.
NH
C(═O)N(CH3)-A-33


 847.
NH
C(═O)N(CH3)—CH2-A-1


 848.
NH
C(═O)N(CH3)—CH2-A-2


 849.
NH
C(═O)N(CH3)—CH2-A-3


 850.
NH
C(═O)N(CH3)—CH2-A-4


 851.
NH
C(═O)N(CH3)—CH2-A-5


 852.
NH
C(═O)N(CH3)—CH2-A-6


 853.
NH
C(═O)N(CH3)—CH2-A-7


 854.
NH
C(═O)N(CH3)—CH2-A-8


 855.
NH
C(═O)N(CH3)—CH2-A-9


 856.
NH
C(═O)N(CH3)—CH2-A-10


 857.
NH
C(═O)N(CH3)—CH2-A-11


 858.
NH
C(═O)N(CH3)—CH2-A-12


 859.
NH
C(═O)N(CH3)—CH2-A-13


 860.
NH
C(═O)N(CH3)—CH2-A-14


 861.
NH
C(═O)N(CH3)—CH2-A-15


 862.
NH
C(═O)N(CH3)—CH2-A-16


 863.
NH
C(═O)N(CH3)—CH2-A-17


 864.
NH
C(═O)N(CH3)—CH2-A-18


 865.
NH
C(═O)N(CH3)—CH2-A-19


 866.
NH
C(═O)N(CH3)—CH2-A-20


 867.
NH
C(═O)N(CH3)—CH2-A-21


 868.
NH
C(═O)N(CH3)—CH2-A-22


 869.
NH
C(═O)N(CH3)—CH2-A-23


 870.
NH
C(═O)N(CH3)—CH2-A-24


 871.
NH
C(═O)N(CH3)—CH2-A-25


 872.
NH
C(═O)N(CH3)—CH2-A-26


 873.
NH
C(═O)N(CH3)—CH2-A-27


 874.
NH
C(═O)N(CH3)—CH2-A-28


 875.
NH
C(═O)N(CH3)—CH2-A-29


 876.
NH
C(═O)N(CH3)—CH2-A-30


 877.
NH
C(═O)N(CH3)—CH2-A-31


 878.
NH
C(═O)N(CH3)—CH2-A-32


 879.
NH
C(═O)N(CH3)—CH2-A-33


 880.
NH
C(═O)N(CH3)—SO2—CH3


 881.
NH
C(═O)N(CH3)—SO2—CF3


 882.
NH
C(═O)N(CH3)—SO2—CH2CH3


 883.
NH
C(═O)N(CH3)—SO2—CH2CF3


 884.
NH
C(═O)N(CH3)—SO2—CH2CH2CH3


 885.
NH
C(═O)N(CH3)—SO2—CH2CH2CF3


 886.
NH
C(═O)N(CH3)—SO2—CH2CF2CF3


 887.
NH
C(═O)N(CH3)—SO2—CH(CH3)2


 888.
NH
C(═O)N(CH3)—SO2—CH(CF3)2


 889.
NH
C(═O)NH—SO2—NH2


 890.
NH
C(═O)NH—SO2—NHCH3


 891.
NH
C(═O)NH—SO2—N(CH3)2


 892.
NH
C(═O)NH—SO2—NHCF3


 893.
NH
C(═O)NH—SO2—N(CF3)2


 894.
NH
C(═O)NH—SO2—NHCH2CH3


 895.
NH
C(═O)NH—SO2—N(CH2CH3)2


 896.
NH
C(═O)NH—SO2—NHCH2CF3


 897.
NH
C(═O)NH—SO2—N(CH2CF3)2


 898.
NH
C(═O)NH—SO2—N(CH3)CH2CH3


 899.
NH
C(═O)NH—SO2—N(CH3)CH2CF3


 900.
NH
C(═O)NH—SO2—N(CF3)CH2CH3


 901.
NH
C(═O)NH—SO2—NHCH2CH2CH3


 902.
NH
C(═O)NH—SO2—N(CH2CH2CH3)2


 903.
NH
C(═O)NH—SO2—NHCH2CH2CF3


 904.
NH
C(═O)NH—SO2—N(CH2CH2CF3)2


 905.
NH
C(═O)NH—SO2—N(CH3)CH2CH2CH3


 906.
NH
C(═O)NH—SO2—N(CH3)CH2CH2CF3


 907.
NH
C(═O)NH—SO2—N(CF3)CH2CH2CH3


 908.
NH
C(═O)NH—SO2—NHCH(CH3)2


 909.
NH
C(═O)NH—SO2—NHCH(CF3)2


 910.
NH
C(═O)NH—SO2—N(CH3)CH(CH3)2


 911.
NH
C(═O)NH—SO2—N(CH3)CH(CF3)2


 912.
NH
C(═O)NH—SO2—N(CF3)CH(CH3)2


 913.
NH
C(═O)NH—SO2—NHCH2CH2CH2CH3


 914.
NH
C(═O)NH—SO2—N(CH2CH2CH2CH3)2


 915.
NH
C(═O)NH—SO2—N(CH3)CH2CH2CH2CH3


 916.
NH
C(═O)N(CH3)—SO2—NH2


 917.
NH
C(═O)N(CH3)—SO2—NHCH3


 918.
NH
C(═O)N(CH3)—SO2—N(CH3)2


 919.
NH
C(═O)N(CH3)—SO2—NHCF3


 920.
NH
C(═O)N(CH3)—SO2—N(CF3)2


 921.
NH
C(═O)N(CH3)—SO2—NHCH2CH3


 922.
NH
C(═O)N(CH3)—SO2—N(CH2CH3)2


 923.
NH
C(═O)N(CH3)—SO2—NHCH2CF3


 924.
NH
C(═O)N(CH3)—SO2—N(CH2CF3)2


 925.
NH
C(═O)N(CH3)—SO2—N(CH3)CH2CH3


 926.
NH
C(═O)N(CH3)—SO2—N(CH3)CH2CF3


 927.
NH
C(═O)N(CH3)—SO2—N(CF3)CH2CH3


 928.
NH
C(═O)N(CH3)—SO2—NHCH2CH2CH3


 929.
NH
C(═O)N(CH3)—SO2—N(CH2CH2CH3)2


 930.
NH
C(═O)N(CH3)—SO2—NHCH2CH2CF3


 931.
NH
C(═O)N(CH3)—SO2—N(CH2CH2CF3)2


 932.
NH
C(═O)N(CH3)—SO2—N(CH3)CH2CH2CH3


 933.
NH
C(═O)N(CH3)—SO2—N(CH3)CH2CH2CF3


 934.
NH
C(═O)N(CH3)—SO2—N(CF3)CH2CH2CH3


 935.
NH
C(═O)N(CH3)—SO2—NHCH(CH3)2


 936.
NH
C(═O)N(CH3)—SO2—NHCH(CF3)2


 937.
NH
C(═O)N(CH3)—SO2—N(CH3)CH(CH3)2


 938.
NH
C(═O)N(CH3)—SO2—N(CH3)CH(CF3)2


 939.
NH
C(═O)N(CH3)—SO2—N(CF3)CH(CH3)2


 940.
NH
C(═O)N(CH3)—SO2—NHCH2CH2CH2CH3


 941.
NH
C(═O)N(CH3)—SO2—N(CH2CH2CH2CH3)2


 942.
NH
C(═O)N(CH3)—SO2—N(CH3)CH2CH2CH2CH3


 943.
NH
C(═O)—N═CHOCH3


 944.
NH
C(═O)—N═CHOCH2CH3


 945.
NH
C(═O)—N═CHOCH2CH2CH3


 946.
NH
C(═O)—N═CHOCH(CH3)2


 947.
NH
C(═O)—N═CHOCF3


 948.
NH
C(═O)—N═CHOCH2CF3


 949.
NH
C(═O)—N═CHOCH2CH2CF3


 950.
NH
C(═O)—N═CHOCH(CF3)2


 951.
NH
C(═O)—N═CH—CO—OCH3


 952.
NH
C(═O)—N═CH—CO—OCH2CH3


 953.
NH
C(═O)—N═CH—CO—OCH2CH2CH3


 954.
NH
C(═O)—N═CH—CO—OCH(CH3)2


 955.
NH
C(═O)—N═CH—CO—OCF3


 956.
NH
C(═O)—N═CH—CO—OCH2CF3


 957.
NH
C(═O)—N═CH—CO—OCH2CH2CF3


 958.
NH
C(═O)—N═CH—CO—OCH(CF3)2


 959.
NH
C(═O)—N═CH—CO—NHCH3


 960.
NH
C(═O)—N═CH—CO—N(CH3)2


 961.
NH
C(═O)—N═CH—CO—NHCH2CH3


 962.
NH
C(═O)—N═CH—CO—N(CH2CH3)2


 963.
NH
C(═O)—N═CH—CO—N(CH3)CH2CH3


 964.
NH
C(═O)—N═CH—CO—NHCH2CH2CH3


 965.
NH
C(═O)—N═CH—CO—N(CH2CH2CH3)2


 966.
NH
C(═O)—N═CH—CO—N(CH3)CH2CH2CH3


 967.
NH
C(═O)—N═CH—CO—NHCH(CH3)2


 968.
NH
C(═O)—N═CH—CO—N(CH3)CH(CH3)2


 969.
NH
C(═O)—N═CH—CO—NHCF3


 970.
NH
C(═O)—N═CH—CO—N(CF3)2


 971.
NH
C(═O)—N═CH—CO—NHCH2CF3


 972.
NH
C(═O)—N═CH—CO—N(CH2CF3)2


 973.
NH
C(═O)—N═CH—CO—N(CH3)CH2CF3


 974.
NH
C(═O)—N═CH—CO—N(CF3)CH2CF3


 975.
NH
C(═O)—N═CH—CO—NHCH2CH2CF3


 976.
NH
C(═O)—N═CH—CO—N(CH2CH2CF3)2


 977.
NH
C(═O)—N═CH—CO—N(CH3)CH2CH2CF3


 978.
NH
C(═O)—N═CH—CO—N(CF3)CH2CH2CH3


 979.
NH
C(═O)—N═CH—CO—NHCH(CF3)2


 980.
NH
C(═O)—N═CH—CO—N(CH3)CH(CF3)2


 981.
NH
C(═O)—N═CH—CO—N(CF3)CH(CH3)2


 982.
NH
C(═S)NH2


 983.
NH
C(═S)NHCH3


 984.
NH
C(═S)N(CH3)2


 985.
NH
C(═S)NHCF3


 986.
NH
C(═S)N(CF3)2


 987.
NH
C(═S)NHCH2CH3


 988.
NH
C(═S)N(CH2CH3)2


 989.
NH
C(═S)(CH3)CH2CH3


 990.
NH
C(═S)NHCH2CF3


 991.
NH
C(═S)N(CH2CF3)2


 992.
NH
C(═S)N(CH3)CH2CF3


 993.
NH
C(═S)NHCH2CH2CH3


 994.
NH
C(═S)N(CH3)CH2CH2CH3


 995.
NH
C(═S)NHCH(CH3)2


 996.
NH
C(═S)NH(CH2)3CH3


 997.
NH
C(═S)N(CH3)—(CH2)3CH3


 998.
NH
C(═S)N[(CH2)3CH3]2


 999.
NH
C(═S)N(CH3)—CH2—C6H5


1000.
NH
C(═S)NH-propargyl


1001.
NH
C(═S)N(CH3)-propargyl


1002.
NH
C(═S)NH—CH2-4-Cl—C6H4


1003.
NH
C(═S)N(CH3)—CH2-4-Cl—C6H4


1004.
NH
C(═S)morpholin-4-yl


1005.
NH
C(═S)NH-3-thiolyl-1,1-dioxid


1006.
NH
C(═S)N(CH3)-3-thiolyl-1,1-dioxid


1007.
NH
C(═S)-azirid-1-yl


1008.
NH
C(═S)-pyrrolidin-1-yl


1009.
NH
C(═S)-piperidin-1-yl


1010.
NH
C(═S)-thiomorpholin-4-yl


1011.
NH
C(═S)NH—CH2CHF2


1012.
NH
C(═S)NH—CH2CH2CHF2


1013.
NH
C(═S)NH—CH2CH2CF3


1014.
NH
C(═S)NH-cyclopropyl


1015.
NH
C(═S)NH-cyclobutyl


1016.
NH
C(═S)NH-cyclopentyl


1017.
NH
C(═S)NH-cyclohexyl


1018.
NH
C(═S)NH—CH2-cyclopropyl


1019.
NH
C(═S)NH—CH2-cyclobutyl


1020.
NH
C(═S)NH—CH2-cyclopentyl


1021.
NH
C(═S)NH—CH2-cyclohexyl


1022.
NH
C(═S)NH—CN


1023.
NH
C(═S)NH—CH2—CN


1024.
NH
C(═S)NH—CH2—CH═CH2


1025.
NH
C(═S)NH—CH2—CH═C(Cl)2


1026.
NH
C(═S)NH—CH2—CH═CH-phenyl


1027.
NH
C(═S)NH—CH2—CH═CH-(4-Cl-phenyl)


1028.
NH
C(═S)NH—CH2—SCH3


1029.
NH
C(═S)NH—CH2—SCF3


1030.
NH
C(═S)NH—CH2—CH2—SCH3


1031.
NH
C(═S)NH—CH2—CH2—SCF3


1032.
NH
C(═S)NH—CH2—SO2—CH3


1033.
NH
C(═S)NH—CH2—SO2—CF3


1034.
NH
C(═S)NH—CH2—CH2—SO2—CH3


1035.
NH
C(═S)NH—CH2—CH2—SO2—CF3


1036.
NH
C(═S)NH—CH2—CO—NH2


1037.
NH
C(═S)NH—CH2—CO—NHCH3


1038.
NH
C(═S)NH—CH2—CO—N(CH3)2


1039.
NH
C(═S)NH—CH2—CO—NHCF3


1040.
NH
C(═S)NH—CH2—CO—N(CF3)2


1041.
NH
C(═S)NH—CH2—CO—NHCH2CH3


1042.
NH
C(═S)NH—CH2—CO—N(CH2CH3)2


1043.
NH
C(═S)NH—CH2—CO—NHCH2CF3


1044.
NH
C(═S)NH—CH2—CO—N(CH2CF3)2


1045.
NH
C(═S)NH—CH2—CO—NHCH2CH2CH3


1046.
NH
C(═S)NH—CH2—CO—N(CH2CH2CH3)2


1047.
NH
C(═S)NH—CH2—CO—NHCH2CH2CF3


1048.
NH
C(═S)NH—CH2—CO—N(CH2CH2CF3)2


1049.
NH
C(═S)NH—CH2—CO—NHCH(CH3)2


1050.
NH
C(═S)NH—CH2—CO—NHCH(CF3)2


1051.
NH
C(═S)NH—CH2—CO—NH-cyclopropyl


1052.
NH
C(═S)NH—CH2—CO—NH—CH2-cyclopropyl


1053.
NH
C(═S)NH—CH2—CO—OH


1054.
NH
C(═S)NH—CH2—CO—OCH3


1055.
NH
C(═S)NH—CH2—CO—OCF3


1056.
NH
C(═S)NH—CH2—CO—OCH2CH3


1057.
NH
C(═S)NH—CH2—CO—OCH2CF3


1058.
NH
C(═S)NH—CH2—CO—OCH2CH2CH3


1059.
NH
C(═S)NH—CH2—CO—OCH(CH3)2


1060.
NH
C(═S)NH—CH2—CO—OCH2CH2CH2CH3


1061.
NH
C(═S)NH—CH2—CO—OCH(CH3)CH2CH3


1062.
NH
C(═S)NH—CH2—CO—OCH2CH(CH3)2


1063.
NH
C(═S)NH—CH2—CO—OC(CH3)3


1064.
NH
C(═S)NH-A-1


1065.
NH
C(═S)NH-A-2


1066.
NH
C(═S)NH-A-3


1067.
NH
C(═S)NH-A-4


1068.
NH
C(═S)NH-A-5


1069.
NH
C(═S)NH-A-6


1070.
NH
C(═S)NH-A-7


1071.
NH
C(═S)NH-A-8


1072.
NH
C(═S)NH-A-9


1073.
NH
C(═S)NH-A-10


1074.
NH
C(═S)NH-A-11


1075.
NH
C(═S)NH-A-12


1076.
NH
C(═S)NH-A-13


1077.
NH
C(═S)NH-A-14


1078.
NH
C(═S)NH-A-15


1079.
NH
C(═S)NH-A-16


1080.
NH
C(═S)NH-A-17


1081.
NH
C(═S)NH-A-18


1082.
NH
C(═S)NH-A-19


1083.
NH
C(═S)NH-A-20


1084.
NH
C(═S)NH-A-21


1085.
NH
C(═S)NH-A-22


1086.
NH
C(═S)NH-A-23


1087.
NH
C(═S)NH-A-24


1088.
NH
C(═S)NH-A-25


1089.
NH
C(═S)NH-A-26


1090.
NH
C(═S)NH-A-27


1091.
NH
C(═S)NH-A-28


1092.
NH
C(═S)NH-A-29


1093.
NH
C(═S)NH-A-30


1094.
NH
C(═S)NH-A-31


1095.
NH
C(═S)NH-A-32


1096.
NH
C(═S)NH-A-33


1097.
NH
C(═S)NH—CH2-A-1


1098.
NH
C(═S)NH—CH2-A-2


1099.
NH
C(═S)NH—CH2-A-3


1100.
NH
C(═S)NH—CH2-A-4


1101.
NH
C(═S)NH—CH2-A-5


1102.
NH
C(═S)NH—CH2-A-6


1103.
NH
C(═S)NH—CH2-A-7


1104.
NH
C(═S)NH—CH2-A-8


1105.
NH
C(═S)NH—CH2-A-9


1106.
NH
C(═S)NH—CH2-A-10


1107.
NH
C(═S)NH—CH2-A-11


1108.
NH
C(═S)NH—CH2-A-12


1109.
NH
C(═S)NH—CH2-A-13


1110.
NH
C(═S)NH—CH2-A-14


1111.
NH
C(═S)NH—CH2-A-15


1112.
NH
C(═S)NH—CH2-A-16


1113.
NH
C(═S)NH—CH2-A-17


1114.
NH
C(═S)NH—CH2-A-18


1115.
NH
C(═S)NH—CH2-A-19


1116.
NH
C(═S)NH—CH2-A-20


1117.
NH
C(═S)NH—CH2-A-21


1118.
NH
C(═S)NH—CH2-A-22


1119.
NH
C(═S)NH—CH2-A-23


1120.
NH
C(═S)NH—CH2-A-24


1121.
NH
C(═S)NH—CH2-A-25


1122.
NH
C(═S)NH—CH2-A-26


1123.
NH
C(═S)NH—CH2-A-27


1124.
NH
C(═S)NH—CH2-A-28


1125.
NH
C(═S)NH—CH2-A-29


1126.
NH
C(═S)NH—CH2-A-30


1127.
NH
C(═S)NH—CH2-A-31


1128.
NH
C(═S)NH—CH2-A-32


1129.
NH
C(═S)NH—CH2-A-33


1130.
NH
C(═S)NH—SO2—CH3


1131.
NH
C(═S)NH—SO2—CF3


1132.
NH
C(═S)NH—SO2—CH2CH3


1133.
NH
C(═S)NH—SO2—CH2CF3


1134.
NH
C(═S)NH—SO2—CH2CH2CH3


1135.
NH
C(═S)NH—SO2—CH2CH2CF3


1136.
NH
C(═S)NH—SO2—CH2CF2CF3


1137.
NH
C(═S)NH—SO2—CH(CH3)2


1138.
NH
C(═S)NH—SO2—CH(CF3)2


1139.
NH
C(═S)N(CH3)—CH2CHF2


1140.
NH
C(═S)N(CH3)—CH2CH2CHF2


1141.
NH
C(═S)N(CH3)—CH2CH2CF3


1142.
NH
C(═S)N(CH3)-cyclopropyl


1143.
NH
C(═S)N(CH3)-cyclobutyl


1144.
NH
C(═S)N(CH3)-cyclopentyl


1145.
NH
C(═S)N(CH3)-cyclohexyl


1146.
NH
C(═S)N(CH3)—CH2-cyclopropyl


1147.
NH
C(═S)N(CH3)—CH2-cyclobutyl


1148.
NH
C(═S)N(CH3)—CH2-cyclopentyl


1149.
NH
C(═S)N(CH3)—CH2-cyclohexyl


1150.
NH
C(═S)N(CH3)—CN


1151.
NH
C(═S)N(CH3)—CH2—CN


1152.
NH
C(═S)N(CH3)—CH2—CH═CH2


1153.
NH
C(═S)N(CH3)—CH2—CH═C(Cl)2


1154.
NH
C(═S)N(CH3)—CH2—CH═CH-phenyl


1155.
NH
C(═S)N(CH3)—CH2—CH═CH-(4-Cl-phenyl)


1156.
NH
C(═S)N(CH3)—CH2—SCH3


1157.
NH
C(═S)N(CH3)—CH2—SCF3


1158.
NH
C(═S)N(CH3)—CH2—CH2—SCH3


1159.
NH
C(═S)N(CH3)—CH2—CH2—SCF3


1160.
NH
C(═S)N(CH3)—CH2—SO2—CH3


1161.
NH
C(═S)N(CH3)—CH2—SO2—CF3


1162.
NH
C(═S)N(CH3)—CH2—CH2—SO2—CH3


1163.
NH
C(═S)N(CH3)—CH2—CH2—SO2—CF3


1164.
NH
C(═S)N(CH3)—CH2—CO—NH2


1165.
NH
C(═S)N(CH3)—CH2—CO—NHCH3


1166.
NH
C(═S)N(CH3)—CH2—CO—N(CH3)2


1167.
NH
C(═S)N(CH3)—CH2—CO—NHCF3


1168.
NH
C(═S)N(CH3)—CH2—CO—N(CF3)2


1169.
NH
C(═S)N(CH3)—CH2—CO—NHCH2CH3


1170.
NH
C(═S)N(CH3)—CH2—CO—N(CH2CH3)2


1171.
NH
C(═S)N(CH3)—CH2—CO—NHCH2CF3


1172.
NH
C(═S)N(CH3)—CH2—CO—N(CH2CF3)2


1173.
NH
C(═S)N(CH3)—CH2—CO—NHCH2CH2CH3


1174.
NH
C(═S)N(CH3)—CH2—CO—N(CH2CH2CH3)2


1175.
NH
C(═S)N(CH3)—CH2—CO—NHCH2CH2CF3


1176.
NH
C(═S)N(CH3)—CH2—CO—N(CH2CH2CF3)2


1177.
NH
C(═S)N(CH3)—CH2—CO—NHCH(CH3)2


1178.
NH
C(═S)N(CH3)—CH2—CO—NHCH(CF3)2


1179.
NH
C(═S)N(CH3)—CH2—CO—NH-cyclopropyl


1180.
NH
C(═S)N(CH3)—CH2—CO—NH—CH2-cyclopropyl


1181.
NH
C(═S)N(CH3)—CH2—CO—OH


1182.
NH
C(═S)N(CH3)—CH2—CO—OCH3


1183.
NH
C(═S)N(CH3)—CH2—CO—OCF3


1184.
NH
C(═S)N(CH3)—CH2—CO—OCH2CH3


1185.
NH
C(═S)N(CH3)—CH2—CO—OCH2CF3


1186.
NH
C(═S)N(CH3)—CH2—CO—OCH2CH2CH3


1187.
NH
C(═S)N(CH3)—CH2—CO—OCH(CH3)2


1188.
NH
C(═S)N(CH3)—CH2—CO—OCH2CH2CH2CH3


1189.
NH
C(═S)N(CH3)—CH2—CO—OCH(CH3)CH2CH3


1190.
NH
C(═S)N(CH3)—CH2—CO—OCH2CH(CH3)2


1191.
NH
C(═S)N(CH3)—CH2—CO—OC(CH3)3


1192.
NH
C(═S)N(CH3)-A-1


1193.
NH
C(═S)N(CH3)-A-2


1194.
NH
C(═S)N(CH3)-A-3


1195.
NH
C(═S)N(CH3)-A-4


1196.
NH
C(═S)N(CH3)-A-5


1197.
NH
C(═S)N(CH3)-A-6


1198.
NH
C(═S)N(CH3)-A-7


1199.
NH
C(═S)N(CH3)-A-8


1200.
NH
C(═S)N(CH3)-A-9


1201.
NH
C(═S)N(CH3)-A-10


1202.
NH
C(═S)N(CH3)-A-11


1203.
NH
C(═S)N(CH3)-A-12


1204.
NH
C(═S)N(CH3)-A-13


1205.
NH
C(═S)N(CH3)-A-14


1206.
NH
C(═S)N(CH3)-A-15


1207.
NH
C(═S)N(CH3)-A-16


1208.
NH
C(═S)N(CH3)-A-17


1209.
NH
C(═S)N(CH3)-A-18


1210.
NH
C(═S)N(CH3)-A-19


1211.
NH
C(═S)N(CH3)-A-20


1212.
NH
C(═S)N(CH3)-A-21


1213.
NH
C(═S)N(CH3)-A-22


1214.
NH
C(═S)N(CH3)-A-23


1215.
NH
C(═S)N(CH3)-A-24


1216.
NH
C(═S)N(CH3)-A-25


1217.
NH
C(═S)N(CH3)-A-26


1218.
NH
C(═S)N(CH3)-A-27


1219.
NH
C(═S)N(CH3)-A-28


1220.
NH
C(═S)N(CH3)-A-29


1221.
NH
C(═S)N(CH3)-A-30


1222.
NH
C(═S)N(CH3)-A-31


1223.
NH
C(═S)N(CH3)-A-32


1224.
NH
C(═S)N(CH3)-A-33


1225.
NH
C(═S)N(CH3)—CH2-A-1


1226.
NH
C(═S)N(CH3)—CH2-A-2


1227.
NH
C(═S)N(CH3)—CH2-A-3


1228.
NH
C(═S)N(CH3)—CH2-A-4


1229.
NH
C(═S)N(CH3)—CH2-A-5


1230.
NH
C(═S)N(CH3)—CH2-A-6


1231.
NH
C(═S)N(CH3)—CH2-A-7


1232.
NH
C(═S)N(CH3)—CH2-A-8


1233.
NH
C(═S)N(CH3)—CH2-A-9


1234.
NH
C(═S)N(CH3)—CH2-A-10


1235.
NH
C(═S)N(CH3)—CH2-A-11


1236.
NH
C(═S)N(CH3)—CH2-A-12


1237.
NH
C(═S)N(CH3)—CH2-A-13


1238.
NH
C(═S)N(CH3)—CH2-A-14


1239.
NH
C(═S)N(CH3)—CH2-A-15


1240.
NH
C(═S)N(CH3)—CH2-A-16


1241.
NH
C(═S)N(CH3)—CH2-A-17


1242.
NH
C(═S)N(CH3)—CH2-A-18


1243.
NH
C(═S)N(CH3)—CH2-A-19


1244.
NH
C(═S)N(CH3)—CH2-A-20


1245.
NH
C(═S)N(CH3)—CH2-A-21


1246.
NH
C(═S)N(CH3)—CH2-A-22


1247.
NH
C(═S)N(CH3)—CH2-A-23


1248.
NH
C(═S)N(CH3)—CH2-A-24


1249.
NH
C(═S)N(CH3)—CH2-A-25


1250.
NH
C(═S)N(CH3)—CH2-A-26


1251.
NH
C(═S)N(CH3)—CH2-A-27


1252.
NH
C(═S)N(CH3)—CH2-A-28


1253.
NH
C(═S)N(CH3)—CH2-A-29


1254.
NH
C(═S)N(CH3)—CH2-A-30


1255.
NH
C(═S)N(CH3)—CH2-A-31


1256.
NH
C(═S)N(CH3)—CH2-A-32


1257.
NH
C(═S)N(CH3)—CH2-A-33


1258.
NH
C(═S)N(CH3)—SO2—CH3


1259.
NH
C(═S)N(CH3)—SO2—CF3


1260.
NH
C(═S)N(CH3)—SO2—CH2CH3


1261.
NH
C(═S)N(CH3)—SO2—CH2CF3


1262.
NH
C(═S)N(CH3)—SO2—CH2CH2CH3


1263.
NH
C(═S)N(CH3)—SO2—CH2CH2CF3


1264.
NH
C(═S)N(CH3)—SO2—CH2CF2CF3


1265.
NH
C(═S)N(CH3)—SO2—CH(CH3)2


1266.
NH
C(═S)N(CH3)—SO2—CH(CF3)2


1267.
NH
C(═S)NH—SO2—NH2


1268.
NH
C(═S)NH—SO2—NHCH3


1269.
NH
C(═S)NH—SO2—N(CH3)2


1270.
NH
C(═S)NH—SO2—NHCF3


1271.
NH
C(═S)NH—SO2—N(CF3)2


1272.
NH
C(═S)NH—SO2—NHCH2CH3


1273.
NH
C(═S)NH—SO2—N(CH2CH3)2


1274.
NH
C(═S)NH—SO2—NHCH2CF3


1275.
NH
C(═S)NH—SO2—N(CH2CF3)2


1276.
NH
C(═S)NH—SO2—N(CH3)CH2CH3


1277.
NH
C(═S)NH—SO2—N(CH3)CH2CF3


1278.
NH
C(═S)NH—SO2—N(CF3)CH2CH3


1279.
NH
C(═S)NH—SO2—NHCH2CH2CH3


1280.
NH
C(═S)NH—SO2—N(CH2CH2CH3)2


1281.
NH
C(═S)NH—SO2—NHCH2CH2CF3


1282.
NH
C(═S)NH—SO2—N(CH2CH2CF3)2


1283.
NH
C(═S)NH—SO2—N(CH3)CH2CH2CH3


1284.
NH
C(═S)NH—SO2—N(CH3)CH2CH2CF3


1285.
NH
C(═S)NH—SO2—N(CF3)CH2CH2CH3


1286.
NH
C(═S)NH—SO2—NHCH(CH3)2


1287.
NH
C(═S)NH—SO2—NHCH(CF3)2


1288.
NH
C(═S)NH—SO2—N(CH3)CH(CH3)2


1289.
NH
C(═S)NH—SO2—N(CH3)CH(CF3)2


1290.
NH
C(═S)NH—SO2—N(CF3)CH(CH3)2


1291.
NH
C(═S)NH—SO2—NHCH2CH2CH2CH3


1292.
NH
C(═S)NH—SO2—N(CH2CH2CH2CH3)2


1293.
NH
C(═S)NH—SO2—N(CH3)CH2CH2CH2CH3


1294.
NH
C(═S)N(CH3)—SO2—NH2


1295.
NH
C(═S)N(CH3)—SO2—NHCH3


1296.
NH
C(═S)N(CH3)—SO2—N(CH3)2


1297.
NH
C(═S)N(CH3)—SO2—NHCF3


1298.
NH
C(═S)N(CH3)—SO2—N(CF3)2


1299.
NH
C(═S)N(CH3)—SO2—NHCH2CH3


1300.
NH
C(═S)N(CH3)—SO2—N(CH2CH3)2


1301.
NH
C(═S)N(CH3)—SO2—NHCH2CF3


1302.
NH
C(═S)N(CH3)—SO2—N(CH2CF3)2


1303.
NH
C(═S)N(CH3)—SO2—N(CH3)CH2CH3


1304.
NH
C(═S)N(CH3)—SO2—N(CH3)CH2CF3


1305.
NH
C(═S)N(CH3)—SO2—N(CF3)CH2CH3


1306.
NH
C(═S)N(CH3)—SO2—NHCH2CH2CH3


1307.
NH
C(═S)N(CH3)—SO2—N(CH2CH2CH3)2


1308.
NH
C(═S)N(CH3)—SO2—NHCH2CH2CF3


1309.
NH
C(═S)N(CH3)—SO2—N(CH2CH2CF3)2


1310.
NH
C(═S)N(CH3)—SO2—N(CH3)CH2CH2CH3


1311.
NH
C(═S)N(CH3)—SO2—N(CH3)CH2CH2CF3


1312.
NH
C(═S)N(CH3)—SO2—N(CF3)CH2CH2CH3


1313.
NH
C(═S)N(CH3)—SO2—NHCH(CH3)2


1314.
NH
C(═S)N(CH3)—SO2—NHCH(CF3)2


1315.
NH
C(═S)N(CH3)—SO2—N(CH3)CH(CH3)2


1316.
NH
C(═S)N(CH3)—SO2—N(CH3)CH(CF3)2


1317.
NH
C(═S)N(CH3)—SO2—N(CF3)CH(CH3)2


1318.
NH
C(═S)N(CH3)—SO2—NHCH2CH2CH2CH3


1319.
NH
C(═S)N(CH3)—SO2—N(CH2CH2CH2CH3)2


1320.
NH
C(═S)N(CH3)—SO2—N(CH3)CH2CH2CH2CH3


1321.
NH
C(═S)—N═CHOCH3


1322.
NH
C(═S)—N═CHOCH2CH3


1323.
NH
C(═S)—N═CHOCH2CH2CH3


1324.
NH
C(═S)—N═CHOCH(CH3)2


1325.
NH
C(═S)—N═CHOCF3


1326.
NH
C(═S)—N═CHOCH2CF3


1327.
NH
C(═S)—N═CHOCH2CH2CF3


1328.
NH
C(═S)—N═CHOCH(CF3)2


1329.
NH
C(═S)—N═CH—CO—OCH3


1330.
NH
C(═S)—N═CH—CO—OCH2CH3


1331.
NH
C(═S)—N═CH—CO—OCH2CH2CH3


1332.
NH
C(═S)—N═CH—CO—OCH(CH3)2


1333.
NH
C(═S)—N═CH—CO—OCF3


1334.
NH
C(═S)—N═CH—CO—OCH2CF3


1335.
NH
C(═S)—N═CH—CO—OCH2CH2CF3


1336.
NH
C(═S)—N═CH—CO—OCH(CF3)2


1337.
NH
C(═S)—N═CH—CO—NHCH3


1338.
NH
C(═S)—N═CH—CO—N(CH3)2


1339.
NH
C(═S)—N═CH—CO—NHCH2CH3


1340.
NH
C(═S)—N═CH—CO—N(CH2CH3)2


1341.
NH
C(═S)—N═CH—CO—N(CH3)CH2CH3


1342.
NH
C(═S)—N═CH—CO—NHCH2CH2CH3


1343.
NH
C(═S)—N═CH—CO—N(CH2CH2CH3)2


1344.
NH
C(═S)—N═CH—CO—N(CH3)CH2CH2CH3


1345.
NH
C(═S)—N═CH—CO—NHCH(CH3)2


1346.
NH
C(═S)—N═CH—CO—N(CH3)CH(CH3)2


1347.
NH
C(═S)—N═CH—CO—NHCF3


1348.
NH
C(═S)—N═CH—CO—N(CF3)2


1349.
NH
C(═S)—N═CH—CO—NHCH2CF3


1350.
NH
C(═S)—N═CH—CO—N(CH2CF3)2


1351.
NH
C(═S)—N═CH—CO—N(CH3)CH2CF3


1352.
NH
C(═S)—N═CH—CO—N(CF3)CH2CF3


1353.
NH
C(═S)—N═CH—CO—NHCH2CH2CF3


1354.
NH
C(═S)—N═CH—CO—N(CH2CH2CF3)2


1355.
NH
C(═S)—N═CH—CO—N(CH3)CH2CH2CF3


1356.
NH
C(═S)—N═CH—CO—N(CF3)CH2CH2CH3


1357.
NH
C(═S)—N═CH—CO—NHCH(CF3)2


1358.
NH
C(═S)—N═CH—CO—N(CH3)CH(CF3)2


1359.
NH
C(═S)—N═CH—CO—N(CF3)CH(CH3)2


1360.
NCH3
C(═O)NH2


1361.
NCH3
C(═O)NHCH3


1362.
NCH3
C(═O)N(CH3)2


1363.
NCH3
C(═O)NHCF3


1364.
NCH3
C(═O)N(CF3)2


1365.
NCH3
C(═O)NHCH2CH3


1366.
NCH3
C(═O)N(CH2CH3)2


1367.
NCH3
C(═O)(CH3)CH2CH3


1368.
NCH3
C(═O)NHCH2CF3


1369.
NCH3
C(═O)N(CH2CF3)2


1370.
NCH3
C(═O)N(CH3)CH2CF3


1371.
NCH3
C(═O)NHCH2CH2CH3


1372.
NCH3
C(═O)N(CH3)CH2CH2CH3


1373.
NCH3
C(═O)NHCH(CH3)2


1374.
NCH3
C(═O)NH(CH2)3CH3


1375.
NCH3
C(═O)N(CH3)—(CH2)3CH3


1376.
NCH3
C(═O)N[(CH2)3CH3]2


1377.
NCH3
C(═O)N(CH3)—CH2—C6H5


1378.
NCH3
C(═O)NH-propargyl


1379.
NCH3
C(═O)N(CH3)-propargyl


1380.
NCH3
C(═O)NH—CH2-4-Cl—C6H4


1381.
NCH3
C(═O)N(CH3)—CH2-4-Cl—C6H4


1382.
NCH3
C(═O)morpholin-4-yl


1383.
NCH3
C(═O)NH-3-thiolyl-1,1-dioxid


1384.
NCH3
C(═O)N(CH3)-3-thiolyl-1,1-dioxid


1385.
NCH3
C(═O)-azirid-1-yl


1386.
NCH3
C(═O)-pyrrolidin-1-yl


1387.
NCH3
C(═O)-piperidin-1-yl


1388.
NCH3
C(═O)-thiomorpholin-4-yl


1389.
NCH3
C(═O)NH—CH2CHF2


1390.
NCH3
C(═O)NH—CH2CH2CHF2


1391.
NCH3
C(═O)NH—CH2CH2CF3


1392.
NCH3
C(═O)NH-cyclopropyl


1393.
NCH3
C(═O)NH-cyclobutyl


1394.
NCH3
C(═O)NH-cyclopentyl


1395.
NCH3
C(═O)NH-cyclohexyl


1396.
NCH3
C(═O)NH—CH2-cyclopropyl


1397.
NCH3
C(═O)NH—CH2-cyclobutyl


1398.
NCH3
C(═O)NH—CH2-cyclopentyl


1399.
NCH3
C(═O)NH—CH2-cyclohexyl


1400.
NCH3
C(═O)NH—CN


1401.
NCH3
C(═O)NH—CH2—CN


1402.
NCH3
C(═O)NH—CH2—CH═CH2


1403.
NCH3
C(═O)NH—CH2—CH═C(Cl)2


1404.
NCH3
C(═O)NH—CH2—CH═CH-phenyl


1405.
NCH3
C(═O)NH—CH2—CH═CH-(4-Cl-phenyl)


1406.
NCH3
C(═O)NH—CH2—SCH3


1407.
NCH3
C(═O)NH—CH2—SCF3


1408.
NCH3
C(═O)NH—CH2—CH2—SCH3


1409.
NCH3
C(═O)NH—CH2—CH2—SCF3


1410.
NCH3
C(═O)NH—CH2—SO2—CH3


1411.
NCH3
C(═O)NH—CH2—SO2—CF3


1412.
NCH3
C(═O)NH—CH2—CH2—SO2—CH3


1413.
NCH3
C(═O)NH—CH2—CH2—SO2—CF3


1414.
NCH3
C(═O)NH—CH2—CO—NH2


1415.
NCH3
C(═O)NH—CH2—CO—NHCH3


1416.
NCH3
C(═O)NH—CH2—CO—N(CH3)2


1417.
NCH3
C(═O)NH—CH2—CO—NHCF3


1418.
NCH3
C(═O)NH—CH2—CO—N(CF3)2


1419.
NCH3
C(═O)NH—CH2—CO—NHCH2CH3


1420.
NCH3
C(═O)NH—CH2—CO—N(CH2CH3)2


1421.
NCH3
C(═O)NH—CH2—CO—NHCH2CF3


1422.
NCH3
C(═O)NH—CH2—CO—N(CH2CF3)2


1423.
NCH3
C(═O)NH—CH2—CO—NHCH2CH2CH3


1424.
NCH3
C(═O)NH—CH2—CO—N(CH2CH2CH3)2


1425.
NCH3
C(═O)NH—CH2—CO—NHCH2CH2CF3


1426.
NCH3
C(═O)NH—CH2—CO—N(CH2CH2CF3)2


1427.
NCH3
C(═O)NH—CH2—CO—NHCH(CH3)2


1428.
NCH3
C(═O)NH—CH2—CO—NHCH(CF3)2


1429.
NCH3
C(═O)NH—CH2—CO—NH-cyclopropyl


1430.
NCH3
C(═O)NH—CH2—CO—NH—CH2-cyclopropyl


1431.
NCH3
C(═O)NH—CH2—CO—OH


1432.
NCH3
C(═O)NH—CH2—CO—OCH3


1433.
NCH3
C(═O)NH—CH2—CO—OCF3


1434.
NCH3
C(═O)NH—CH2—CO—OCH2CH3


1435.
NCH3
C(═O)NH—CH2—CO—OCH2CF3


1436.
NCH3
C(═O)NH—CH2—CO—OCH2CH2CH3


1437.
NCH3
C(═O)NH—CH2—CO—OCH(CH3)2


1438.
NCH3
C(═O)NH—CH2—CO—OCH2CH2CH2CH3


1439.
NCH3
C(═O)NH—CH2—CO—OCH(CH3)CH2CH3


1440.
NCH3
C(═O)NH—CH2—CO—OCH2CH(CH3)2


1441.
NCH3
C(═O)NH—CH2—CO—OC(CH3)3


1442.
NCH3
C(═O)NH-A-1


1443.
NCH3
C(═O)NH-A-2


1444.
NCH3
C(═O)NH-A-3


1445.
NCH3
C(═O)NH-A-4


1446.
NCH3
C(═O)NH-A-5


1447.
NCH3
C(═O)NH-A-6


1448.
NCH3
C(═O)NH-A-7


1449.
NCH3
C(═O)NH-A-8


1450.
NCH3
C(═O)NH-A-9


1451.
NCH3
C(═O)NH-A-10


1452.
NCH3
C(═O)NH-A-11


1453.
NCH3
C(═O)NH-A-12


1454.
NCH3
C(═O)NH-A-13


1455.
NCH3
C(═O)NH-A-14


1456.
NCH3
C(═O)NH-A-15


1457.
NCH3
C(═O)NH-A-16


1458.
NCH3
C(═O)NH-A-17


1459.
NCH3
C(═O)NH-A-18


1460.
NCH3
C(═O)NH-A-19


1461.
NCH3
C(═O)NH-A-20


1462.
NCH3
C(═O)NH-A-21


1463.
NCH3
C(═O)NH-A-22


1464.
NCH3
C(═O)NH-A-23


1465.
NCH3
C(═O)NH-A-24


1466.
NCH3
C(═O)NH-A-25


1467.
NCH3
C(═O)NH-A-26


1468.
NCH3
C(═O)NH-A-27


1469.
NCH3
C(═O)NH-A-28


1470.
NCH3
C(═O)NH-A-29


1471.
NCH3
C(═O)NH-A-30


1472.
NCH3
C(═O)NH-A-31


1473.
NCH3
C(═O)NH-A-32


1474.
NCH3
C(═O)NH-A-33


1475.
NCH3
C(═O)NH—CH2-A-1


1476.
NCH3
C(═O)NH—CH2-A-2


1477.
NCH3
C(═O)NH—CH2-A-3


1478.
NCH3
C(═O)NH—CH2-A-4


1479.
NCH3
C(═O)NH—CH2-A-5


1480.
NCH3
C(═O)NH—CH2-A-6


1481.
NCH3
C(═O)NH—CH2-A-7


1482.
NCH3
C(═O)NH—CH2-A-8


1483.
NCH3
C(═O)NH—CH2-A-9


1484.
NCH3
C(═O)NH—CH2-A-10


1485.
NCH3
C(═O)NH—CH2-A-11


1486.
NCH3
C(═O)NH—CH2-A-12


1487.
NCH3
C(═O)NH—CH2-A-13


1488.
NCH3
C(═O)NH—CH2-A-14


1489.
NCH3
C(═O)NH—CH2-A-15


1490.
NCH3
C(═O)NH—CH2-A-16


1491.
NCH3
C(═O)NH—CH2-A-17


1492.
NCH3
C(═O)NH—CH2-A-18


1493.
NCH3
C(═O)NH—CH2-A-19


1494.
NCH3
C(═O)NH—CH2-A-20


1495.
NCH3
C(═O)NH—CH2-A-21


1496.
NCH3
C(═O)NH—CH2-A-22


1497.
NCH3
C(═O)NH—CH2-A-23


1498.
NCH3
C(═O)NH—CH2-A-24


1499.
NCH3
C(═O)NH—CH2-A-25


1500.
NCH3
C(═O)NH—CH2-A-26


1501.
NCH3
C(═O)NH—CH2-A-27


1502.
NCH3
C(═O)NH—CH2-A-28


1503.
NCH3
C(═O)NH—CH2-A-29


1504.
NCH3
C(═O)NH—CH2-A-30


1505.
NCH3
C(═O)NH—CH2-A-31


1506.
NCH3
C(═O)NH—CH2-A-32


1507.
NCH3
C(═O)NH—CH2-A-33


1508.
NCH3
C(═O)NH—SO2—CH3


1509.
NCH3
C(═O)NH—SO2—CF3


1510.
NCH3
C(═O)NH—SO2—CH2CH3


1511.
NCH3
C(═O)NH—SO2—CH2CF3


1512.
NCH3
C(═O)NH—SO2—CH2CH2CH3


1513.
NCH3
C(═O)NH—SO2—CH2CH2CF3


1514.
NCH3
C(═O)NH—SO2—CH2CF2CF3


1515.
NCH3
C(═O)NH—SO2—CH(CH3)2


1516.
NCH3
C(═O)NH—SO2—CH(CF3)2


1517.
NCH3
C(═O)N(CH3)—CH2CHF2


1518.
NCH3
C(═O)N(CH3)—CH2CH2CHF2


1519.
NCH3
C(═O)N(CH3)—CH2CH2CF3


1520.
NCH3
C(═O)N(CH3)-cyclopropyl


1521.
NCH3
C(═O)N(CH3)-cyclobutyl


1522.
NCH3
C(═O)N(CH3)-cyclopentyl


1523.
NCH3
C(═O)N(CH3)-cyclohexyl


1524.
NCH3
C(═O)N(CH3)—CH2-cyclopropyl


1525.
NCH3
C(═O)N(CH3)—CH2-cyclobutyl


1526.
NCH3
C(═O)N(CH3)—CH2-cyclopentyl


1527.
NCH3
C(═O)N(CH3)—CH2-cyclohexyl


1528.
NCH3
C(═O)N(CH3)—CN


1529.
NCH3
C(═O)N(CH3)—CH2—CN


1530.
NCH3
C(═O)N(CH3)—CH2—CH═CH2


1531.
NCH3
C(═O)N(CH3)—CH2—CH═C(Cl)2


1532.
NCH3
C(═O)N(CH3)—CH2—CH═CH-phenyl


1533.
NCH3
C(═O)N(CH3)—CH2—CH═CH-(4-Cl-phenyl)


1534.
NCH3
C(═O)N(CH3)—CH2—SCH3


1535.
NCH3
C(═O)N(CH3)—CH2—SCF3


1536.
NCH3
C(═O)N(CH3)—CH2—CH2—SCH3


1537.
NCH3
C(═O)N(CH3)—CH2—CH2—SCF3


1538.
NCH3
C(═O)N(CH3)—CH2—SO2—CH3


1539.
NCH3
C(═O)N(CH3)—CH2—SO2—CF3


1540.
NCH3
C(═O)N(CH3)—CH2—CH2—SO2—CH3


1541.
NCH3
C(═O)N(CH3)—CH2—CH2—SO2—CF3


1542.
NCH3
C(═O)N(CH3)—CH2—CO—NH2


1543.
NCH3
C(═O)N(CH3)—CH2—CO—NHCH3


1544.
NCH3
C(═O)N(CH3)—CH2—CO—N(CH3)2


1545.
NCH3
C(═O)N(CH3)—CH2—CO—NHCF3


1546.
NCH3
C(═O)N(CH3)—CH2—CO—N(CF3)2


1547.
NCH3
C(═O)N(CH3)—CH2—CO—NHCH2CH3


1548.
NCH3
C(═O)N(CH3)—CH2—CO—N(CH2CH3)2


1549.
NCH3
C(═O)N(CH3)—CH2—CO—NHCH2CF3


1550.
NCH3
C(═O)N(CH3)—CH2—CO—N(CH2CF3)2


1551.
NCH3
C(═O)N(CH3)—CH2—CO—NHCH2CH2CH3


1552.
NCH3
C(═O)N(CH3)—CH2—CO—N(CH2CH2CH3)2


1553.
NCH3
C(═O)N(CH3)—CH2—CO—NHCH2CH2CF3


1554.
NCH3
C(═O)N(CH3)—CH2—CO—N(CH2CH2CF3)2


1555.
NCH3
C(═O)N(CH3)—CH2—CO—NHCH(CH3)2


1556.
NCH3
C(═O)N(CH3)—CH2—CO—NHCH(CF3)2


1557.
NCH3
C(═O)N(CH3)—CH2—CO—NH-cyclopropyl


1558.
NCH3
C(═O)N(CH3)—CH2—CO—NH—CH2-cyclopropyl


1559.
NCH3
C(═O)N(CH3)—CH2—CO—OH


1560.
NCH3
C(═O)N(CH3)—CH2—CO—OCH3


1561.
NCH3
C(═O)N(CH3)—CH2—CO—OCF3


1562.
NCH3
C(═O)N(CH3)—CH2—CO—OCH2CH3


1563.
NCH3
C(═O)N(CH3)—CH2—CO—OCH2CF3


1564.
NCH3
C(═O)N(CH3)—CH2—CO—OCH2CH2CH3


1565.
NCH3
C(═O)N(CH3)—CH2—CO—OCH(CH3)2


1566.
NCH3
C(═O)N(CH3)—CH2—CO—OCH2CH2CH2CH3


1567.
NCH3
C(═O)N(CH3)—CH2—CO—OCH(CH3)CH2CH3


1568.
NCH3
C(═O)N(CH3)—CH2—CO—OCH2CH(CH3)2


1569.
NCH3
C(═O)N(CH3)—CH2—CO—OC(CH3)3


1570.
NCH3
C(═O)N(CH3)-A-1


1571.
NCH3
C(═O)N(CH3)-A-2


1572.
NCH3
C(═O)N(CH3)-A-3


1573.
NCH3
C(═O)N(CH3)-A-4


1574.
NCH3
C(═O)N(CH3)-A-5


1575.
NCH3
C(═O)N(CH3)-A-6


1576.
NCH3
C(═O)N(CH3)-A-7


1577.
NCH3
C(═O)N(CH3)-A-8


1578.
NCH3
C(═O)N(CH3)-A-9


1579.
NCH3
C(═O)N(CH3)-A-10


1580.
NCH3
C(═O)N(CH3)-A-11


1581.
NCH3
C(═O)N(CH3)-A-12


1582.
NCH3
C(═O)N(CH3)-A-13


1583.
NCH3
C(═O)N(CH3)-A-14


1584.
NCH3
C(═O)N(CH3)-A-15


1585.
NCH3
C(═O)N(CH3)-A-16


1586.
NCH3
C(═O)N(CH3)-A-17


1587.
NCH3
C(═O)N(CH3)-A-18


1588.
NCH3
C(═O)N(CH3)-A-19


1589.
NCH3
C(═O)N(CH3)-A-20


1590.
NCH3
C(═O)N(CH3)-A-21


1591.
NCH3
C(═O)N(CH3)-A-22


1592.
NCH3
C(═O)N(CH3)-A-23


1593.
NCH3
C(═O)N(CH3)-A-24


1594.
NCH3
C(═O)N(CH3)-A-25


1595.
NCH3
C(═O)N(CH3)-A-26


1596.
NCH3
C(═O)N(CH3)-A-27


1597.
NCH3
C(═O)N(CH3)-A-28


1598.
NCH3
C(═O)N(CH3)-A-29


1599.
NCH3
C(═O)N(CH3)-A-30


1600.
NCH3
C(═O)N(CH3)-A-31


1601.
NCH3
C(═O)N(CH3)-A-32


1602.
NCH3
C(═O)N(CH3)-A-33


1603.
NCH3
C(═O)N(CH3)—CH2-A-1


1604.
NCH3
C(═O)N(CH3)—CH2-A-2


1605.
NCH3
C(═O)N(CH3)—CH2-A-3


1606.
NCH3
C(═O)N(CH3)—CH2-A-4


1607.
NCH3
C(═O)N(CH3)—CH2-A-5


1608.
NCH3
C(═O)N(CH3)—CH2-A-6


1609.
NCH3
C(═O)N(CH3)—CH2-A-7


1610.
NCH3
C(═O)N(CH3)—CH2-A-8


1611.
NCH3
C(═O)N(CH3)—CH2-A-9


1612.
NCH3
C(═O)N(CH3)—CH2-A-10


1613.
NCH3
C(═O)N(CH3)—CH2-A-11


1614.
NCH3
C(═O)N(CH3)—CH2-A-12


1615.
NCH3
C(═O)N(CH3)—CH2-A-13


1616.
NCH3
C(═O)N(CH3)—CH2-A-14


1617.
NCH3
C(═O)N(CH3)—CH2-A-15


1618.
NCH3
C(═O)N(CH3)—CH2-A-16


1619.
NCH3
C(═O)N(CH3)—CH2-A-17


1620.
NCH3
C(═O)N(CH3)—CH2-A-18


1621.
NCH3
C(═O)N(CH3)—CH2-A-19


1622.
NCH3
C(═O)N(CH3)—CH2-A-20


1623.
NCH3
C(═O)N(CH3)—CH2-A-21


1624.
NCH3
C(═O)N(CH3)—CH2-A-22


1625.
NCH3
C(═O)N(CH3)—CH2-A-23


1626.
NCH3
C(═O)N(CH3)—CH2-A-24


1627.
NCH3
C(═O)N(CH3)—CH2-A-25


1628.
NCH3
C(═O)N(CH3)—CH2-A-26


1629.
NCH3
C(═O)N(CH3)—CH2-A-27


1630.
NCH3
C(═O)N(CH3)—CH2-A-28


1631.
NCH3
C(═O)N(CH3)—CH2-A-29


1632.
NCH3
C(═O)N(CH3)—CH2-A-30


1633.
NCH3
C(═O)N(CH3)—CH2-A-31


1634.
NCH3
C(═O)N(CH3)—CH2-A-32


1635.
NCH3
C(═O)N(CH3)—CH2-A-33


1636.
NCH3
C(═O)N(CH3)—SO2—CH3


1637.
NCH3
C(═O)N(CH3)—SO2—CF3


1638.
NCH3
C(═O)N(CH3)—SO2—CH2CH3


1639.
NCH3
C(═O)N(CH3)—SO2—CH2CF3


1640.
NCH3
C(═O)N(CH3)—SO2—CH2CH2CH3


1641.
NCH3
C(═O)N(CH3)—SO2—CH2CH2CF3


1642.
NCH3
C(═O)N(CH3)—SO2—CH2CF2CF3


1643.
NCH3
C(═O)N(CH3)—SO2—CH(CH3)2


1644.
NCH3
C(═O)N(CH3)—SO2—CH(CF3)2


1645.
NCH3
C(═O)NH—SO2—NH2


1646.
NCH3
C(═O)NH—SO2—NHCH3


1647.
NCH3
C(═O)NH—SO2—N(CH3)2


1648.
NCH3
C(═O)NH—SO2—NHCF3


1649.
NCH3
C(═O)NH—SO2—N(CF3)2


1650.
NCH3
C(═O)NH—SO2—NHCH2CH3


1651.
NCH3
C(═O)NH—SO2—N(CH2CH3)2


1652.
NCH3
C(═O)NH—SO2—NHCH2CF3


1653.
NCH3
C(═O)NH—SO2—N(CH2CF3)2


1654.
NCH3
C(═O)NH—SO2—N(CH3)CH2CH3


1655.
NCH3
C(═O)NH—SO2—N(CH3)CH2CF3


1656.
NCH3
C(═O)NH—SO2—N(CF3)CH2CH3


1657.
NCH3
C(═O)NH—SO2—NHCH2CH2CH3


1658.
NCH3
C(═O)NH—SO2—N(CH2CH2CH3)2


1659.
NCH3
C(═O)NH—SO2—NHCH2CH2CF3


1660.
NCH3
C(═O)NH—SO2—N(CH2CH2CF3)2


1661.
NCH3
C(═O)NH—SO2—N(CH3)CH2CH2CH3


1662.
NCH3
C(═O)NH—SO2—N(CH3)CH2CH2CF3


1663.
NCH3
C(═O)NH—SO2—N(CF3)CH2CH2CH3


1664.
NCH3
C(═O)NH—SO2—NHCH(CH3)2


1665.
NCH3
C(═O)NH—SO2—NHCH(CF3)2


1666.
NCH3
C(═O)NH—SO2—N(CH3)CH(CH3)2


1667.
NCH3
C(═O)NH—SO2—N(CH3)CH(CF3)2


1668.
NCH3
C(═O)NH—SO2—N(CF3)CH(CH3)2


1669.
NCH3
C(═O)NH—SO2—NHCH2CH2CH2CH3


1670.
NCH3
C(═O)NH—SO2—N(CH2CH2CH2CH3)2


1671.
NCH3
C(═O)NH—SO2—N(CH3)CH2CH2CH2CH3


1672.
NCH3
C(═O)N(CH3)—SO2—NH2


1673.
NCH3
C(═O)N(CH3)—SO2—NHCH3


1674.
NCH3
C(═O)N(CH3)—SO2—N(CH3)2


1675.
NCH3
C(═O)N(CH3)—SO2—NHCF3


1676.
NCH3
C(═O)N(CH3)—SO2—N(CF3)2


1677.
NCH3
C(═O)N(CH3)—SO2—NHCH2CH3


1678.
NCH3
C(═O)N(CH3)—SO2—N(CH2CH3)2


1679.
NCH3
C(═O)N(CH3)—SO2—NHCH2CF3


1680.
NCH3
C(═O)N(CH3)—SO2—N(CH2CF3)2


1681.
NCH3
C(═O)N(CH3)—SO2—N(CH3)CH2CH3


1682.
NCH3
C(═O)N(CH3)—SO2—N(CH3)CH2CF3


1683.
NCH3
C(═O)N(CH3)—SO2—N(CF3)CH2CH3


1684.
NCH3
C(═O)N(CH3)—SO2—NHCH2CH2CH3


1685.
NCH3
C(═O)N(CH3)—SO2—N(CH2CH2CH3)2


1686.
NCH3
C(═O)N(CH3)—SO2—NHCH2CH2CF3


1687.
NCH3
C(═O)N(CH3)—SO2—N(CH2CH2CF3)2


1688.
NCH3
C(═O)N(CH3)—SO2—N(CH3)CH2CH2CH3


1689.
NCH3
C(═O)N(CH3)—SO2—N(CH3)CH2CH2CF3


1690.
NCH3
C(═O)N(CH3)—SO2—N(CF3)CH2CH2CH3


1691.
NCH3
C(═O)N(CH3)—SO2—NHCH(CH3)2


1692.
NCH3
C(═O)N(CH3)—SO2—NHCH(CF3)2


1693.
NCH3
C(═O)N(CH3)—SO2—N(CH3)CH(CH3)2


1694.
NCH3
C(═O)N(CH3)—SO2—N(CH3)CH(CF3)2


1695.
NCH3
C(═O)N(CH3)—SO2—N(CF3)CH(CH3)2


1696.
NCH3
C(═O)N(CH3)—SO2—NHCH2CH2CH2CH3


1697.
NCH3
C(═O)N(CH3)—SO2—N(CH2CH2CH2CH3)2


1698.
NCH3
C(═O)N(CH3)—SO2—N(CH3)CH2CH2CH2CH3


1699.
NCH3
C(═O)—N═CHOCH3


1700.
NCH3
C(═O)—N═CHOCH2CH3


1701.
NCH3
C(═O)—N═CHOCH2CH2CH3


1702.
NCH3
C(═O)—N═CHOCH(CH3)2


1703.
NCH3
C(═O)—N═CHOCF3


1704.
NCH3
C(═O)—N═CHOCH2CF3


1705.
NCH3
C(═O)—N═CHOCH2CH2CF3


1706.
NCH3
C(═O)—N═CHOCH(CF3)2


1707.
NCH3
C(═O)—N═CH—CO—OCH3


1708.
NCH3
C(═O)—N═CH—CO—OCH2CH3


1709.
NCH3
C(═O)—N═CH—CO—OCH2CH2CH3


1710.
NCH3
C(═O)—N═CH—CO—OCH(CH3)2


1711.
NCH3
C(═O)—N═CH—CO—OCF3


1712.
NCH3
C(═O)—N═CH—CO—OCH2CF3


1713.
NCH3
C(═O)—N═CH—CO—OCH2CH2CF3


1714.
NCH3
C(═O)—N═CH—CO—OCH(CF3)2


1715.
NCH3
C(═O)—N═CH—CO—NHCH3


1716.
NCH3
C(═O)—N═CH—CO—N(CH3)2


1717.
NCH3
C(═O)—N═CH—CO—NHCH2CH3


1718.
NCH3
C(═O)—N═CH—CO—N(CH2CH3)2


1719.
NCH3
C(═O)—N═CH—CO—N(CH3)CH2CH3


1720.
NCH3
C(═O)—N═CH—CO—NHCH2CH2CH3


1721.
NCH3
C(═O)—N═CH—CO—N(CH2CH2CH3)2


1722.
NCH3
C(═O)—N═CH—CO—N(CH3)CH2CH2CH3


1723.
NCH3
C(═O)—N═CH—CO—NHCH(CH3)2


1724.
NCH3
C(═O)—N═CH—CO—N(CH3)CH(CH3)2


1725.
NCH3
C(═O)—N═CH—CO—NHCF3


1726.
NCH3
C(═O)—N═CH—CO—N(CF3)2


1727.
NCH3
C(═O)—N═CH—CO—NHCH2CF3


1728.
NCH3
C(═O)—N═CH—CO—N(CH2CF3)2


1729.
NCH3
C(═O)—N═CH—CO—N(CH3)CH2CF3


1730.
NCH3
C(═O)—N═CH—CO—N(CF3)CH2CF3


1731.
NCH3
C(═O)—N═CH—CO—NHCH2CH2CF3


1732.
NCH3
C(═O)—N═CH—CO—N(CH2CH2CF3)2


1733.
NCH3
C(═O)—N═CH—CO—N(CH3)CH2CH2CF3


1734.
NCH3
C(═O)—N═CH—CO—N(CF3)CH2CH2CH3


1735.
NCH3
C(═O)—N═CH—CO—NHCH(CF3)2


1736.
NCH3
C(═O)—N═CH—CO—N(CH3)CH(CF3)2


1737.
NCH3
C(═O)—N═CH—CO—N(CF3)CH(CH3)2


1738.
NCH3
C(═S)NH2


1739.
NCH3
C(═S)NHCH3


1740.
NCH3
C(═S)N(CH3)2


1741.
NCH3
C(═S)NHCF3


1742.
NCH3
C(═S)N(CF3)2


1743.
NCH3
C(═S)NHCH2CH3


1744.
NCH3
C(═S)N(CH2CH3)2


1745.
NCH3
C(═S)(CH3)CH2CH3


1746.
NCH3
C(═S)NHCH2CF3


1747.
NCH3
C(═S)N(CH2CF3)2


1748.
NCH3
C(═S)N(CH3)CH2CF3


1749.
NCH3
C(═S)NHCH2CH2CH3


1750.
NCH3
C(═S)N(CH3)CH2CH2CH3


1751.
NCH3
C(═S)NHCH(CH3)2


1752.
NCH3
C(═S)NH(CH2)3CH3


1753.
NCH3
C(═S)N(CH3)—(CH2)3CH3


1754.
NCH3
C(═S)N[(CH2)3CH3]2


1755.
NCH3
C(═S)N(CH3)—CH2—C6H5


1756.
NCH3
C(═S)NH-propargyl


1757.
NCH3
C(═S)N(CH3)-propargyl


1758.
NCH3
C(═S)NH—CH2-4-Cl—C6H4


1759.
NCH3
C(═S)N(CH3)—CH2-4-Cl—C6H4


1760.
NCH3
C(═S)morpholin-4-yl


1761.
NCH3
C(═S)NH-3-thiolyl-1,1-dioxid


1762.
NCH3
C(═S)N(CH3)-3-thiolyl-1,1-dioxid


1763.
NCH3
C(═S)-azirid-1-yl


1764.
NCH3
C(═S)-pyrrolidin-1-yl


1765.
NCH3
C(═S)-piperidin-1-yl


1766.
NCH3
C(═S)-thiomorpholin-4-yl


1767.
NCH3
C(═S)NH—CH2CHF2


1768.
NCH3
C(═S)NH—CH2CH2CHF2


1769.
NCH3
C(═S)NH—CH2CH2CF3


1770.
NCH3
C(═S)NH-cyclopropyl


1771.
NCH3
C(═S)NH-cyclobutyl


1772.
NCH3
C(═S)NH-cyclopentyl


1773.
NCH3
C(═S)NH-cyclohexyl


1774.
NCH3
C(═S)NH—CH2-cyclopropyl


1775.
NCH3
C(═S)NH—CH2-cyclobutyl


1776.
NCH3
C(═S)NH—CH2-cyclopentyl


1777.
NCH3
C(═S)NH—CH2-cyclohexyl


1778.
NCH3
C(═S)NH—CN


1779.
NCH3
C(═S)NH—CH2—CN


1780.
NCH3
C(═S)NH—CH2—CH═CH2


1781.
NCH3
C(═S)NH—CH2—CH═C(Cl)2


1782.
NCH3
C(═S)NH—CH2—CH═CH-phenyl


1783.
NCH3
C(═S)NH—CH2—CH═CH-(4-Cl-phenyl)


1784.
NCH3
C(═S)NH—CH2—SCH3


1785.
NCH3
C(═S)NH—CH2—SCF3


1786.
NCH3
C(═S)NH—CH2—CH2—SCH3


1787.
NCH3
C(═S)NH—CH2—CH2—SCF3


1788.
NCH3
C(═S)NH—CH2—SO2—CH3


1789.
NCH3
C(═S)NH—CH2—SO2—CF3


1790.
NCH3
C(═S)NH—CH2—CH2—SO2—CH3


1791.
NCH3
C(═S)NH—CH2—CH2—SO2—CF3


1792.
NCH3
C(═S)NH—CH2—CO—NH2


1793.
NCH3
C(═S)NH—CH2—CO—NHCH3


1794.
NCH3
C(═S)NH—CH2—CO—N(CH3)2


1795.
NCH3
C(═S)NH—CH2—CO—NHCF3


1796.
NCH3
C(═S)NH—CH2—CO—N(CF3)2


1797.
NCH3
C(═S)NH—CH2—CO—NHCH2CH3


1798.
NCH3
C(═S)NH—CH2—CO—N(CH2CH3)2


1799.
NCH3
C(═S)NH—CH2—CO—NHCH2CF3


1800.
NCH3
C(═S)NH—CH2—CO—N(CH2CF3)2


1801.
NCH3
C(═S)NH—CH2—CO—NHCH2CH2CH3


1802.
NCH3
C(═S)NH—CH2—CO—N(CH2CH2CH3)2


1803.
NCH3
C(═S)NH—CH2—CO—NHCH2CH2CF3


1804.
NCH3
C(═S)NH—CH2—CO—N(CH2CH2CF3)2


1805.
NCH3
C(═S)NH—CH2—CO—NHCH(CH3)2


1806.
NCH3
C(═S)NH—CH2—CO—NHCH(CF3)2


1807.
NCH3
C(═S)NH—CH2—CO—NH-cyclopropyl


1808.
NCH3
C(═S)NH—CH2—CO—NH—CH2-cyclopropyl


1809.
NCH3
C(═S)NH—CH2—CO—OH


1810.
NCH3
C(═S)NH—CH2—CO—OCH3


1811.
NCH3
C(═S)NH—CH2—CO—OCF3


1812.
NCH3
C(═S)NH—CH2—CO—OCH2CH3


1813.
NCH3
C(═S)NH—CH2—CO—OCH2CF3


1814.
NCH3
C(═S)NH—CH2—CO—OCH2CH2CH3


1815.
NCH3
C(═S)NH—CH2—CO—OCH(CH3)2


1816.
NCH3
C(═S)NH—CH2—CO—OCH2CH2CH2CH3


1817.
NCH3
C(═S)NH—CH2—CO—OCH(CH3)CH2CH3


1818.
NCH3
C(═S)NH—CH2—CO—OCH2CH(CH3)2


1819.
NCH3
C(═S)NH—CH2—CO—OC(CH3)3


1820.
NCH3
C(═S)NH-A-1


1821.
NCH3
C(═S)NH-A-2


1822.
NCH3
C(═S)NH-A-3


1823.
NCH3
C(═S)NH-A-4


1824.
NCH3
C(═S)NH-A-5


1825.
NCH3
C(═S)NH-A-6


1826.
NCH3
C(═S)NH-A-7


1827.
NCH3
C(═S)NH-A-8


1828.
NCH3
C(═S)NH-A-9


1829.
NCH3
C(═S)NH-A-10


1830.
NCH3
C(═S)NH-A-11


1831.
NCH3
C(═S)NH-A-12


1832.
NCH3
C(═S)NH-A-13


1833.
NCH3
C(═S)NH-A-14


1834.
NCH3
C(═S)NH-A-15


1835.
NCH3
C(═S)NH-A-16


1836.
NCH3
C(═S)NH-A-17


1837.
NCH3
C(═S)NH-A-18


1838.
NCH3
C(═S)NH-A-19


1839.
NCH3
C(═S)NH-A-20


1840.
NCH3
C(═S)NH-A-21


1841.
NCH3
C(═S)NH-A-22


1842.
NCH3
C(═S)NH-A-23


1843.
NCH3
C(═S)NH-A-24


1844.
NCH3
C(═S)NH-A-25


1845.
NCH3
C(═S)NH-A-26


1846.
NCH3
C(═S)NH-A-27


1847.
NCH3
C(═S)NH-A-28


1848.
NCH3
C(═S)NH-A-29


1849.
NCH3
C(═S)NH-A-30


1850.
NCH3
C(═S)NH-A-31


1851.
NCH3
C(═S)NH-A-32


1852.
NCH3
C(═S)NH-A-33


1853.
NCH3
C(═S)NH—CH2-A-1


1854.
NCH3
C(═S)NH—CH2-A-2


1855.
NCH3
C(═S)NH—CH2-A-3


1856.
NCH3
C(═S)NH—CH2-A-4


1857.
NCH3
C(═S)NH—CH2-A-5


1858.
NCH3
C(═S)NH—CH2-A-6


1859.
NCH3
C(═S)NH—CH2-A-7


1860.
NCH3
C(═S)NH—CH2-A-8


1861.
NCH3
C(═S)NH—CH2-A-9


1862.
NCH3
C(═S)NH—CH2-A-10


1863.
NCH3
C(═S)NH—CH2-A-11


1864.
NCH3
C(═S)NH—CH2-A-12


1865.
NCH3
C(═S)NH—CH2-A-13


1866.
NCH3
C(═S)NH—CH2-A-14


1867.
NCH3
C(═S)NH—CH2-A-15


1868.
NCH3
C(═S)NH—CH2-A-16


1869.
NCH3
C(═S)NH—CH2-A-17


1870.
NCH3
C(═S)NH—CH2-A-18


1871.
NCH3
C(═S)NH—CH2-A-19


1872.
NCH3
C(═S)NH—CH2-A-20


1873.
NCH3
C(═S)NH—CH2-A-21


1874.
NCH3
C(═S)NH—CH2-A-22


1875.
NCH3
C(═S)NH—CH2-A-23


1876.
NCH3
C(═S)NH—CH2-A-24


1877.
NCH3
C(═S)NH—CH2-A-25


1878.
NCH3
C(═S)NH—CH2-A-26


1879.
NCH3
C(═S)NH—CH2-A-27


1880.
NCH3
C(═S)NH—CH2-A-28


1881.
NCH3
C(═S)NH—CH2-A-29


1882.
NCH3
C(═S)NH—CH2-A-30


1883.
NCH3
C(═S)NH—CH2-A-31


1884.
NCH3
C(═S)NH—CH2-A-32


1885.
NCH3
C(═S)NH—CH2-A-33


1886.
NCH3
C(═S)NH—SO2—CH3


1887.
NCH3
C(═S)NH—SO2—CF3


1888.
NCH3
C(═S)NH—SO2—CH2CH3


1889.
NCH3
C(═S)NH—SO2—CH2CF3


1890.
NCH3
C(═S)NH—SO2—CH2CH2CH3


1891.
NCH3
C(═S)NH—SO2—CH2CH2CF3


1892.
NCH3
C(═S)NH—SO2—CH2CF2CF3


1893.
NCH3
C(═S)NH—SO2—CH(CH3)2


1894.
NCH3
C(═S)NH—SO2—CH(CF3)2


1895.
NCH3
C(═S)N(CH3)—CH2CHF2


1896.
NCH3
C(═S)N(CH3)—CH2CH2CHF2


1897.
NCH3
C(═S)N(CH3)—CH2CH2CF3


1898.
NCH3
C(═S)N(CH3)-cyclopropyl


1899.
NCH3
C(═S)N(CH3)-cyclobutyl


1900.
NCH3
C(═S)N(CH3)-cyclopentyl


1901.
NCH3
C(═S)N(CH3)-cyclohexyl


1902.
NCH3
C(═S)N(CH3)—CH2-cyclopropyl


1903.
NCH3
C(═S)N(CH3)—CH2-cyclobutyl


1904.
NCH3
C(═S)N(CH3)—CH2-cyclopentyl


1905.
NCH3
C(═S)N(CH3)—CH2-cyclohexyl


1906.
NCH3
C(═S)N(CH3)—CN


1907.
NCH3
C(═S)N(CH3)—CH2—CN


1908.
NCH3
C(═S)N(CH3)—CH2—CH═CH2


1909.
NCH3
C(═S)N(CH3)—CH2—CH═C(Cl)2


1910.
NCH3
C(═S)N(CH3)—CH2—CH═CH-phenyl


1911.
NCH3
C(═S)N(CH3)—CH2—CH═CH-(4-Cl-phenyl)


1912.
NCH3
C(═S)N(CH3)—CH2—SCH3


1913.
NCH3
C(═S)N(CH3)—CH2—SCF3


1914.
NCH3
C(═S)N(CH3)—CH2—CH2—SCH3


1915.
NCH3
C(═S)N(CH3)—CH2—CH2—SCF3


1916.
NCH3
C(═S)N(CH3)—CH2—SO2—CH3


1917.
NCH3
C(═S)N(CH3)—CH2—SO2—CF3


1918.
NCH3
C(═S)N(CH3)—CH2—CH2—SO2—CH3


1919.
NCH3
C(═S)N(CH3)—CH2—CH2—SO2—CF3


1920.
NCH3
C(═S)N(CH3)—CH2—CO—NH2


1921.
NCH3
C(═S)N(CH3)—CH2—CO—NHCH3


1922.
NCH3
C(═S)N(CH3)—CH2—CO—N(CH3)2


1923.
NCH3
C(═S)N(CH3)—CH2—CO—NHCF3


1924.
NCH3
C(═S)N(CH3)—CH2—CO—N(CF3)2


1925.
NCH3
C(═S)N(CH3)—CH2—CO—NHCH2CH3


1926.
NCH3
C(═S)N(CH3)—CH2—CO—N(CH2CH3)2


1927.
NCH3
C(═S)N(CH3)—CH2—CO—NHCH2CF3


1928.
NCH3
C(═S)N(CH3)—CH2—CO—N(CH2CF3)2


1929.
NCH3
C(═S)N(CH3)—CH2—CO—NHCH2CH2CH3


1930.
NCH3
C(═S)N(CH3)—CH2—CO—N(CH2CH2CH3)2


1931.
NCH3
C(═S)N(CH3)—CH2—CO—NHCH2CH2CF3


1932.
NCH3
C(═S)N(CH3)—CH2—CO—N(CH2CH2CF3)2


1933.
NCH3
C(═S)N(CH3)—CH2—CO—NHCH(CH3)2


1934.
NCH3
C(═S)N(CH3)—CH2—CO—NHCH(CF3)2


1935.
NCH3
C(═S)N(CH3)—CH2—CO—NH-cyclopropyl


1936.
NCH3
C(═S)N(CH3)—CH2—CO—NH—CH2-cyclopropyl


1937.
NCH3
C(═S)N(CH3)—CH2—CO—OH


1938.
NCH3
C(═S)N(CH3)—CH2—CO—OCH3


1939.
NCH3
C(═S)N(CH3)—CH2—CO—OCF3


1940.
NCH3
C(═S)N(CH3)—CH2—CO—OCH2CH3


1941.
NCH3
C(═S)N(CH3)—CH2—CO—OCH2CF3


1942.
NCH3
C(═S)N(CH3)—CH2—CO—OCH2CH2CH3


1943.
NCH3
C(═S)N(CH3)—CH2—CO—OCH(CH3)2


1944.
NCH3
C(═S)N(CH3)—CH2—CO—OCH2CH2CH2CH3


1945.
NCH3
C(═S)N(CH3)—CH2—CO—OCH(CH3)CH2CH3


1946.
NCH3
C(═S)N(CH3)—CH2—CO—OCH2CH(CH3)2


1947.
NCH3
C(═S)N(CH3)—CH2—CO—OC(CH3)3


1948.
NCH3
C(═S)N(CH3)-A-1


1949.
NCH3
C(═S)N(CH3)-A-2


1950.
NCH3
C(═S)N(CH3)-A-3


1951.
NCH3
C(═S)N(CH3)-A-4


1952.
NCH3
C(═S)N(CH3)-A-5


1953.
NCH3
C(═S)N(CH3)-A-6


1954.
NCH3
C(═S)N(CH3)-A-7


1955.
NCH3
C(═S)N(CH3)-A-8


1956.
NCH3
C(═S)N(CH3)-A-9


1957.
NCH3
C(═S)N(CH3)-A-10


1958.
NCH3
C(═S)N(CH3)-A-11


1959.
NCH3
C(═S)N(CH3)-A-12


1960.
NCH3
C(═S)N(CH3)-A-13


1961.
NCH3
C(═S)N(CH3)-A-14


1962.
NCH3
C(═S)N(CH3)-A-15


1963.
NCH3
C(═S)N(CH3)-A-16


1964.
NCH3
C(═S)N(CH3)-A-17


1965.
NCH3
C(═S)N(CH3)-A-18


1966.
NCH3
C(═S)N(CH3)-A-19


1967.
NCH3
C(═S)N(CH3)-A-20


1968.
NCH3
C(═S)N(CH3)-A-21


1969.
NCH3
C(═S)N(CH3)-A-22


1970.
NCH3
C(═S)N(CH3)-A-23


1971.
NCH3
C(═S)N(CH3)-A-24


1972.
NCH3
C(═S)N(CH3)-A-25


1973.
NCH3
C(═S)N(CH3)-A-26


1974.
NCH3
C(═S)N(CH3)-A-27


1975.
NCH3
C(═S)N(CH3)-A-28


1976.
NCH3
C(═S)N(CH3)-A-29


1977.
NCH3
C(═S)N(CH3)-A-30


1978.
NCH3
C(═S)N(CH3)-A-31


1979.
NCH3
C(═S)N(CH3)-A-32


1980.
NCH3
C(═S)N(CH3)-A-33


1981.
NCH3
C(═S)N(CH3)—CH2-A-1


1982.
NCH3
C(═S)N(CH3)—CH2-A-2


1983.
NCH3
C(═S)N(CH3)—CH2-A-3


1984.
NCH3
C(═S)N(CH3)—CH2-A-4


1985.
NCH3
C(═S)N(CH3)—CH2-A-5


1986.
NCH3
C(═S)N(CH3)—CH2-A-6


1987.
NCH3
C(═S)N(CH3)—CH2-A-7


1988.
NCH3
C(═S)N(CH3)—CH2-A-8


1989.
NCH3
C(═S)N(CH3)—CH2-A-9


1990.
NCH3
C(═S)N(CH3)—CH2-A-10


1991.
NCH3
C(═S)N(CH3)—CH2-A-11


1992.
NCH3
C(═S)N(CH3)—CH2-A-12


1993.
NCH3
C(═S)N(CH3)—CH2-A-13


1994.
NCH3
C(═S)N(CH3)—CH2-A-14


1995.
NCH3
C(═S)N(CH3)—CH2-A-15


1996.
NCH3
C(═S)N(CH3)—CH2-A-16


1997.
NCH3
C(═S)N(CH3)—CH2-A-17


1998.
NCH3
C(═S)N(CH3)—CH2-A-18


1999.
NCH3
C(═S)N(CH3)—CH2-A-19


2000.
NCH3
C(═S)N(CH3)—CH2-A-20


2001.
NCH3
C(═S)N(CH3)—CH2-A-21


2002.
NCH3
C(═S)N(CH3)—CH2-A-22


2003.
NCH3
C(═S)N(CH3)—CH2-A-23


2004.
NCH3
C(═S)N(CH3)—CH2-A-24


2005.
NCH3
C(═S)N(CH3)—CH2-A-25


2006.
NCH3
C(═S)N(CH3)—CH2-A-26


2007.
NCH3
C(═S)N(CH3)—CH2-A-27


2008.
NCH3
C(═S)N(CH3)—CH2-A-28


2009.
NCH3
C(═S)N(CH3)—CH2-A-29


2010.
NCH3
C(═S)N(CH3)—CH2-A-30


2011.
NCH3
C(═S)N(CH3)—CH2-A-31


2012.
NCH3
C(═S)N(CH3)—CH2-A-32


2013.
NCH3
C(═S)N(CH3)—CH2-A-33


2014.
NCH3
C(═S)N(CH3)—SO2—CH3


2015.
NCH3
C(═S)N(CH3)—SO2—CF3


2016.
NCH3
C(═S)N(CH3)—SO2—CH2CH3


2017.
NCH3
C(═S)N(CH3)—SO2—CH2CF3


2018.
NCH3
C(═S)N(CH3)—SO2—CH2CH2CH3


2019.
NCH3
C(═S)N(CH3)—SO2—CH2CH2CF3


2020.
NCH3
C(═S)N(CH3)—SO2—CH2CF2CF3


2021.
NCH3
C(═S)N(CH3)—SO2—CH(CH3)2


2022.
NCH3
C(═S)N(CH3)—SO2—CH(CF3)2


2023.
NCH3
C(═S)NH—SO2—NH2


2024.
NCH3
C(═S)NH—SO2—NHCH3


2025.
NCH3
C(═S)NH—SO2—N(CH3)2


2026.
NCH3
C(═S)NH—SO2—NHCF3


2027.
NCH3
C(═S)NH—SO2—N(CF3)2


2028.
NCH3
C(═S)NH—SO2—NHCH2CH3


2029.
NCH3
C(═S)NH—SO2—N(CH2CH3)2


2030.
NCH3
C(═S)NH—SO2—NHCH2CF3


2031.
NCH3
C(═S)NH—SO2—N(CH2CF3)2


2032.
NCH3
C(═S)NH—SO2—N(CH3)CH2CH3


2033.
NCH3
C(═S)NH—SO2—N(CH3)CH2CF3


2034.
NCH3
C(═S)NH—SO2—N(CF3)CH2CH3


2035.
NCH3
C(═S)NH—SO2—NHCH2CH2CH3


2036.
NCH3
C(═S)NH—SO2—N(CH2CH2CH3)2


2037.
NCH3
C(═S)NH—SO2—NHCH2CH2CF3


2038.
NCH3
C(═S)NH—SO2—N(CH2CH2CF3)2


2039.
NCH3
C(═S)NH—SO2—N(CH3)CH2CH2CH3


2040.
NCH3
C(═S)NH—SO2—N(CH3)CH2CH2CF3


2041.
NCH3
C(═S)NH—SO2—N(CF3)CH2CH2CH3


2042.
NCH3
C(═S)NH—SO2—NHCH(CH3)2


2043.
NCH3
C(═S)NH—SO2—NHCH(CF3)2


2044.
NCH3
C(═S)NH—SO2—N(CH3)CH(CH3)2


2045.
NCH3
C(═S)NH—SO2—N(CH3)CH(CF3)2


2046.
NCH3
C(═S)NH—SO2—N(CF3)CH(CH3)2


2047.
NCH3
C(═S)NH—SO2—NHCH2CH2CH2CH3


2048.
NCH3
C(═S)NH—SO2—N(CH2CH2CH2CH3)2


2049.
NCH3
C(═S)NH—SO2—N(CH3)CH2CH2CH2CH3


2050.
NCH3
C(═S)N(CH3)—SO2—NH2


2051.
NCH3
C(═S)N(CH3)—SO2—NHCH3


2052.
NCH3
C(═S)N(CH3)—SO2—N(CH3)2


2053.
NCH3
C(═S)N(CH3)—SO2—NHCF3


2054.
NCH3
C(═S)N(CH3)—SO2—N(CF3)2


2055.
NCH3
C(═S)N(CH3)—SO2—NHCH2CH3


2056.
NCH3
C(═S)N(CH3)—SO2—N(CH2CH3)2


2057.
NCH3
C(═S)N(CH3)—SO2—NHCH2CF3


2058.
NCH3
C(═S)N(CH3)—SO2—N(CH2CF3)2


2059.
NCH3
C(═S)N(CH3)—SO2—N(CH3)CH2CH3


2060.
NCH3
C(═S)N(CH3)—SO2—N(CH3)CH2CF3


2061.
NCH3
C(═S)N(CH3)—SO2—N(CF3)CH2CH3


2062.
NCH3
C(═S)N(CH3)—SO2—NHCH2CH2CH3


2063.
NCH3
C(═S)N(CH3)—SO2—N(CH2CH2CH3)2


2064.
NCH3
C(═S)N(CH3)—SO2—NHCH2CH2CF3


2065.
NCH3
C(═S)N(CH3)—SO2—N(CH2CH2CF3)2


2066.
NCH3
C(═S)N(CH3)—SO2—N(CH3)CH2CH2CH3


2067.
NCH3
C(═S)N(CH3)—SO2—N(CH3)CH2CH2CF3


2068.
NCH3
C(═S)N(CH3)—SO2—N(CF3)CH2CH2CH3


2069.
NCH3
C(═S)N(CH3)—SO2—NHCH(CH3)2


2070.
NCH3
C(═S)N(CH3)—SO2—NHCH(CF3)2


2071.
NCH3
C(═S)N(CH3)—SO2—N(CH3)CH(CH3)2


2072.
NCH3
C(═S)N(CH3)—SO2—N(CH3)CH(CF3)2


2073.
NCH3
C(═S)N(CH3)—SO2—N(CF3)CH(CH3)2


2074.
NCH3
C(═S)N(CH3)—SO2—NHCH2CH2CH2CH3


2075.
NCH3
C(═S)N(CH3)—SO2—N(CH2CH2CH2CH3)2


2076.
NCH3
C(═S)N(CH3)—SO2—N(CH3)CH2CH2CH2CH3


2077.
NCH3
C(═S)—N═CHOCH3


2078.
NCH3
C(═S)—N═CHOCH2CH3


2079.
NCH3
C(═S)—N═CHOCH2CH2CH3


2080.
NCH3
C(═S)—N═CHOCH(CH3)2


2081.
NCH3
C(═S)—N═CHOCF3


2082.
NCH3
C(═S)—N═CHOCH2CF3


2083.
NCH3
C(═S)—N═CHOCH2CH2CF3


2084.
NCH3
C(═S)—N═CHOCH(CF3)2


2085.
NCH3
C(═S)—N═CH—CO—OCH3


2086.
NCH3
C(═S)—N═CH—CO—OCH2CH3


2087.
NCH3
C(═S)—N═CH—CO—OCH2CH2CH3


2088.
NCH3
C(═S)—N═CH—CO—OCH(CH3)2


2089.
NCH3
C(═S)—N═CH—CO—OCF3


2090.
NCH3
C(═S)—N═CH—CO—OCH2CF3


2091.
NCH3
C(═S)—N═CH—CO—OCH2CH2CF3


2092.
NCH3
C(═S)—N═CH—CO—OCH(CF3)2


2093.
NCH3
C(═S)—N═CH—CO—NHCH3


2094.
NCH3
C(═S)—N═CH—CO—N(CH3)2


2095.
NCH3
C(═S)—N═CH—CO—NHCH2CH3


2096.
NCH3
C(═S)—N═CH—CO—N(CH2CH3)2


2097.
NCH3
C(═S)—N═CH—CO—N(CH3)CH2CH3


2098.
NCH3
C(═S)—N═CH—CO—NHCH2CH2CH3


2099.
NCH3
C(═S)—N═CH—CO—N(CH2CH2CH3)2


2100.
NCH3
C(═S)—N═CH—CO—N(CH3)CH2CH2CH3


2101.
NCH3
C(═S)—N═CH—CO—NHCH(CH3)2


2102.
NCH3
C(═S)—N═CH—CO—N(CH3)CH(CH3)2


2103.
NCH3
C(═S)—N═CH—CO—NHCF3


2104.
NCH3
C(═S)—N═CH—CO—N(CF3)2


2105.
NCH3
C(═S)—N═CH—CO—NHCH2CF3


2106.
NCH3
C(═S)—N═CH—CO—N(CH2CF3)2


2107.
NCH3
C(═S)—N═CH—CO—N(CH3)CH2CF3


2108.
NCH3
C(═S)—N═CH—CO—N(CF3)CH2CF3


2109.
NCH3
C(═S)—N═CH—CO—NHCH2CH2CF3


2110.
NCH3
C(═S)—N═CH—CO—N(CH2CH2CF3)2


2111.
NCH3
C(═S)—N═CH—CO—N(CH3)CH2CH2CF3


2112.
NCH3
C(═S)—N═CH—CO—N(CF3)CH2CH2CH3


2113.
NCH3
C(═S)—N═CH—CO—NHCH(CF3)2


2114.
NCH3
C(═S)—N═CH—CO—N(CH3)CH(CF3)2


2115.
NCH3
C(═S)—N═CH—CO—N(CF3)CH(CH3)2


2116.
NC(O)CH3
C(═O)NH2


2117.
NC(O)CH3
C(═O)NHCH3


2118.
NC(O)CH3
C(═O)N(CH3)2


2119.
NC(O)CH3
C(═O)NHCF3


2120.
NC(O)CH3
C(═O)N(CF3)2


2121.
NC(O)CH3
C(═O)NHCH2CH3


2122.
NC(O)CH3
C(═O)N(CH2CH3)2


2123.
NC(O)CH3
C(═O)(CH3)CH2CH3


2124.
NC(O)CH3
C(═O)NHCH2CF3


2125.
NC(O)CH3
C(═O)N(CH2CF3)2


2126.
NC(O)CH3
C(═O)N(CH3)CH2CF3


2127.
NC(O)CH3
C(═O)NHCH2CH2CH3


2128.
NC(O)CH3
C(═O)N(CH3)CH2CH2CH3


2129.
NC(O)CH3
C(═O)NHCH(CH3)2


2130.
NC(O)CH3
C(═O)NH(CH2)3CH3


2131.
NC(O)CH3
C(═O)N(CH3)—(CH2)3CH3


2132.
NC(O)CH3
C(═O)N[(CH2)3CH3]2


2133.
NC(O)CH3
C(═O)N(CH3)—CH2—C6H5


2134.
NC(O)CH3
C(═O)NH-propargyl


2135.
NC(O)CH3
C(═O)N(CH3)-propargyl


2136.
NC(O)CH3
C(═O)NH—CH2-4-Cl—C6H4


2137.
NC(O)CH3
C(═O)N(CH3)—CH2-4-Cl—C6H4


2138.
NC(O)CH3
C(═O)morpholin-4-yl


2139.
NC(O)CH3
C(═O)NH-3-thiolyl-1,1-dioxid


2140.
NC(O)CH3
C(═O)N(CH3)-3-thiolyl-1,1-dioxid


2141.
NC(O)CH3
C(═O)-azirid-1-yl


2142.
NC(O)CH3
C(═O)-pyrrolidin-1-yl


2143.
NC(O)CH3
C(═O)-piperidin-1-yl


2144.
NC(O)CH3
C(═O)-thiomorpholin-4-yl


2145.
NC(O)CH3
C(═O)NH—CH2CHF2


2146.
NC(O)CH3
C(═O)NH—CH2CH2CHF2


2147.
NC(O)CH3
C(═O)NH—CH2CH2CF3


2148.
NC(O)CH3
C(═O)NH-cyclopropyl


2149.
NC(O)CH3
C(═O)NH-cyclobutyl


2150.
NC(O)CH3
C(═O)NH-cyclopentyl


2151.
NC(O)CH3
C(═O)NH-cyclohexyl


2152.
NC(O)CH3
C(═O)NH—CH2-cyclopropyl


2153.
NC(O)CH3
C(═O)NH—CH2-cyclobutyl


2154.
NC(O)CH3
C(═O)NH—CH2-cyclopentyl


2155.
NC(O)CH3
C(═O)NH—CH2-cyclohexyl


2156.
NC(O)CH3
C(═O)NH—CN


2157.
NC(O)CH3
C(═O)NH—CH2—CN


2158.
NC(O)CH3
C(═O)NH—CH2—CH═CH2


2159.
NC(O)CH3
C(═O)NH—CH2—CH═C(Cl)2


2160.
NC(O)CH3
C(═O)NH—CH2—CH═CH-phenyl


2161.
NC(O)CH3
C(═O)NH—CH2—CH═CH-(4-Cl-phenyl)


2162.
NC(O)CH3
C(═O)NH—CH2—SCH3


2163.
NC(O)CH3
C(═O)NH—CH2—SCF3


2164.
NC(O)CH3
C(═O)NH—CH2—CH2—SCH3


2165.
NC(O)CH3
C(═O)NH—CH2—CH2—SCF3


2166.
NC(O)CH3
C(═O)NH—CH2—SO2—CH3


2167.
NC(O)CH3
C(═O)NH—CH2—SO2—CF3


2168.
NC(O)CH3
C(═O)NH—CH2—CH2—SO2—CH3


2169.
NC(O)CH3
C(═O)NH—CH2—CH2—SO2—CF3


2170.
NC(O)CH3
C(═O)NH—CH2—CO—NH2


2171.
NC(O)CH3
C(═O)NH—CH2—CO—NHCH3


2172.
NC(O)CH3
C(═O)NH—CH2—CO—N(CH3)2


2173.
NC(O)CH3
C(═O)NH—CH2—CO—NHCF3


2174.
NC(O)CH3
C(═O)NH—CH2—CO—N(CF3)2


2175.
NC(O)CH3
C(═O)NH—CH2—CO—NHCH2CH3


2176.
NC(O)CH3
C(═O)NH—CH2—CO—N(CH2CH3)2


2177.
NC(O)CH3
C(═O)NH—CH2—CO—NHCH2CF3


2178.
NC(O)CH3
C(═O)NH—CH2—CO—N(CH2CF3)2


2179.
NC(O)CH3
C(═O)NH—CH2—CO—NHCH2CH2CH3


2180.
NC(O)CH3
C(═O)NH—CH2—CO—N(CH2CH2CH3)2


2181.
NC(O)CH3
C(═O)NH—CH2—CO—NHCH2CH2CF3


2182.
NC(O)CH3
C(═O)NH—CH2—CO—N(CH2CH2CF3)2


2183.
NC(O)CH3
C(═O)NH—CH2—CO—NHCH(CH3)2


2184.
NC(O)CH3
C(═O)NH—CH2—CO—NHCH(CF3)2


2185.
NC(O)CH3
C(═O)NH—CH2—CO—NH-cyclopropyl


2186.
NC(O)CH3
C(═O)NH—CH2—CO—NH—CH2-cyclopropyl


2187.
NC(O)CH3
C(═O)NH—CH2—CO—OH


2188.
NC(O)CH3
C(═O)NH—CH2—CO—OCH3


2189.
NC(O)CH3
C(═O)NH—CH2—CO—OCF3


2190.
NC(O)CH3
C(═O)NH—CH2—CO—OCH2CH3


2191.
NC(O)CH3
C(═O)NH—CH2—CO—OCH2CF3


2192.
NC(O)CH3
C(═O)NH—CH2—CO—OCH2CH2CH3


2193.
NC(O)CH3
C(═O)NH—CH2—CO—OCH(CH3)2


2194.
NC(O)CH3
C(═O)NH—CH2—CO—OCH2CH2CH2CH3


2195.
NC(O)CH3
C(═O)NH—CH2—CO—OCH(CH3)CH2CH3


2196.
NC(O)CH3
C(═O)NH—CH2—CO—OCH2CH(CH3)2


2197.
NC(O)CH3
C(═O)NH—CH2—CO—OC(CH3)3


2198.
NC(O)CH3
C(═O)NH-A-1


2199.
NC(O)CH3
C(═O)NH-A-2


2200.
NC(O)CH3
C(═O)NH-A-3


2201.
NC(O)CH3
C(═O)NH-A-4


2202.
NC(O)CH3
C(═O)NH-A-5


2203.
NC(O)CH3
C(═O)NH-A-6


2204.
NC(O)CH3
C(═O)NH-A-7


2205.
NC(O)CH3
C(═O)NH-A-8


2206.
NC(O)CH3
C(═O)NH-A-9


2207.
NC(O)CH3
C(═O)NH-A-10


2208.
NC(O)CH3
C(═O)NH-A-11


2209.
NC(O)CH3
C(═O)NH-A-12


2210.
NC(O)CH3
C(═O)NH-A-13


2211.
NC(O)CH3
C(═O)NH-A-14


2212.
NC(O)CH3
C(═O)NH-A-15


2213.
NC(O)CH3
C(═O)NH-A-16


2214.
NC(O)CH3
C(═O)NH-A-17


2215.
NC(O)CH3
C(═O)NH-A-18


2216.
NC(O)CH3
C(═O)NH-A-19


2217.
NC(O)CH3
C(═O)NH-A-20


2218.
NC(O)CH3
C(═O)NH-A-21


2219.
NC(O)CH3
C(═O)NH-A-22


2220.
NC(O)CH3
C(═O)NH-A-23


2221.
NC(O)CH3
C(═O)NH-A-24


2222.
NC(O)CH3
C(═O)NH-A-25


2223.
NC(O)CH3
C(═O)NH-A-26


2224.
NC(O)CH3
C(═O)NH-A-27


2225.
NC(O)CH3
C(═O)NH-A-28


2226.
NC(O)CH3
C(═O)NH-A-29


2227.
NC(O)CH3
C(═O)NH-A-30


2228.
NC(O)CH3
C(═O)NH-A-31


2229.
NC(O)CH3
C(═O)NH-A-32


2230.
NC(O)CH3
C(═O)NH-A-33


2231.
NC(O)CH3
C(═O)NH—CH2-A-1


2232.
NC(O)CH3
C(═O)NH—CH2-A-2


2233.
NC(O)CH3
C(═O)NH—CH2-A-3


2234.
NC(O)CH3
C(═O)NH—CH2-A-4


2235.
NC(O)CH3
C(═O)NH—CH2-A-5


2236.
NC(O)CH3
C(═O)NH—CH2-A-6


2237.
NC(O)CH3
C(═O)NH—CH2-A-7


2238.
NC(O)CH3
C(═O)NH—CH2-A-8


2239.
NC(O)CH3
C(═O)NH—CH2-A-9


2240.
NC(O)CH3
C(═O)NH—CH2-A-10


2241.
NC(O)CH3
C(═O)NH—CH2-A-11


2242.
NC(O)CH3
C(═O)NH—CH2-A-12


2243.
NC(O)CH3
C(═O)NH—CH2-A-13


2244.
NC(O)CH3
C(═O)NH—CH2-A-14


2245.
NC(O)CH3
C(═O)NH—CH2-A-15


2246.
NC(O)CH3
C(═O)NH—CH2-A-16


2247.
NC(O)CH3
C(═O)NH—CH2-A-17


2248.
NC(O)CH3
C(═O)NH—CH2-A-18


2249.
NC(O)CH3
C(═O)NH—CH2-A-19


2250.
NC(O)CH3
C(═O)NH—CH2-A-20


2251.
NC(O)CH3
C(═O)NH—CH2-A-21


2252.
NC(O)CH3
C(═O)NH—CH2-A-22


2253.
NC(O)CH3
C(═O)NH—CH2-A-23


2254.
NC(O)CH3
C(═O)NH—CH2-A-24


2255.
NC(O)CH3
C(═O)NH—CH2-A-25


2256.
NC(O)CH3
C(═O)NH—CH2-A-26


2257.
NC(O)CH3
C(═O)NH—CH2-A-27


2258.
NC(O)CH3
C(═O)NH—CH2-A-28


2259.
NC(O)CH3
C(═O)NH—CH2-A-29


2260.
NC(O)CH3
C(═O)NH—CH2-A-30


2261.
NC(O)CH3
C(═O)NH—CH2-A-31


2262.
NC(O)CH3
C(═O)NH—CH2-A-32


2263.
NC(O)CH3
C(═O)NH—CH2-A-33


2264.
NC(O)CH3
C(═O)NH—SO2—CH3


2265.
NC(O)CH3
C(═O)NH—SO2—CF3


2266.
NC(O)CH3
C(═O)NH—SO2—CH2CH3


2267.
NC(O)CH3
C(═O)NH—SO2—CH2CF3


2268.
NC(O)CH3
C(═O)NH—SO2—CH2CH2CH3


2269.
NC(O)CH3
C(═O)NH—SO2—CH2CH2CF3


2270.
NC(O)CH3
C(═O)NH—SO2—CH2CF2CF3


2271.
NC(O)CH3
C(═O)NH—SO2—CH(CH3)2


2272.
NC(O)CH3
C(═O)NH—SO2—CH(CF3)2


2273.
NC(O)CH3
C(═O)N(CH3)—CH2CHF2


2274.
NC(O)CH3
C(═O)N(CH3)—CH2CH2CHF2


2275.
NC(O)CH3
C(═O)N(CH3)—CH2CH2CF3


2276.
NC(O)CH3
C(═O)N(CH3)-cyclopropyl


2277.
NC(O)CH3
C(═O)N(CH3)-cyclobutyl


2278.
NC(O)CH3
C(═O)N(CH3)-cyclopentyl


2279.
NC(O)CH3
C(═O)N(CH3)-cyclohexyl


2280.
NC(O)CH3
C(═O)N(CH3)—CH2-cyclopropyl


2281.
NC(O)CH3
C(═O)N(CH3)—CH2-cyclobutyl


2282.
NC(O)CH3
C(═O)N(CH3)—CH2-cyclopentyl


2283.
NC(O)CH3
C(═O)N(CH3)—CH2-cyclohexyl


2284.
NC(O)CH3
C(═O)N(CH3)—CN


2285.
NC(O)CH3
C(═O)N(CH3)—CH2—CN


2286.
NC(O)CH3
C(═O)N(CH3)—CH2—CH═CH2


2287.
NC(O)CH3
C(═O)N(CH3)—CH2—CH═C(Cl)2


2288.
NC(O)CH3
C(═O)N(CH3)—CH2—CH═CH-phenyl


2289.
NC(O)CH3
C(═O)N(CH3)—CH2—CH═CH-(4-Cl-phenyl)


2290.
NC(O)CH3
C(═O)N(CH3)—CH2—SCH3


2291.
NC(O)CH3
C(═O)N(CH3)—CH2—SCF3


2292.
NC(O)CH3
C(═O)N(CH3)—CH2—CH2—SCH3


2293.
NC(O)CH3
C(═O)N(CH3)—CH2—CH2—SCF3


2294.
NC(O)CH3
C(═O)N(CH3)—CH2—SO2—CH3


2295.
NC(O)CH3
C(═O)N(CH3)—CH2—SO2—CF3


2296.
NC(O)CH3
C(═O)N(CH3)—CH2—CH2—SO2—CH3


2297.
NC(O)CH3
C(═O)N(CH3)—CH2—CH2—SO2—CF3


2298.
NC(O)CH3
C(═O)N(CH3)—CH2—CO—NH2


2299.
NC(O)CH3
C(═O)N(CH3)—CH2—CO—NHCH3


2300.
NC(O)CH3
C(═O)N(CH3)—CH2—CO—N(CH3)2


2301.
NC(O)CH3
C(═O)N(CH3)—CH2—CO—NHCF3


2302.
NC(O)CH3
C(═O)N(CH3)—CH2—CO—N(CF3)2


2303.
NC(O)CH3
C(═O)N(CH3)—CH2—CO—NHCH2CH3


2304.
NC(O)CH3
C(═O)N(CH3)—CH2—CO—N(CH2CH3)2


2305.
NC(O)CH3
C(═O)N(CH3)—CH2—CO—NHCH2CF3


2306.
NC(O)CH3
C(═O)N(CH3)—CH2—CO—N(CH2CF3)2


2307.
NC(O)CH3
C(═O)N(CH3)—CH2—CO—NHCH2CH2CH3


2308.
NC(O)CH3
C(═O)N(CH3)—CH2—CO—N(CH2CH2CH3)2


2309.
NC(O)CH3
C(═O)N(CH3)—CH2—CO—NHCH2CH2CF3


2310.
NC(O)CH3
C(═O)N(CH3)—CH2—CO—N(CH2CH2CF3)2


2311.
NC(O)CH3
C(═O)N(CH3)—CH2—CO—NHCH(CH3)2


2312.
NC(O)CH3
C(═O)N(CH3)—CH2—CO—NHCH(CF3)2


2313.
NC(O)CH3
C(═O)N(CH3)—CH2—CO—NH-cyclopropyl


2314.
NC(O)CH3
C(═O)N(CH3)—CH2—CO—NH—CH2-cyclopropyl


2315.
NC(O)CH3
C(═O)N(CH3)—CH2—CO—OH


2316.
NC(O)CH3
C(═O)N(CH3)—CH2—CO—OCH3


2317.
NC(O)CH3
C(═O)N(CH3)—CH2—CO—OCF3


2318.
NC(O)CH3
C(═O)N(CH3)—CH2—CO—OCH2CH3


2319.
NC(O)CH3
C(═O)N(CH3)—CH2—CO—OCH2CF3


2320.
NC(O)CH3
C(═O)N(CH3)—CH2—CO—OCH2CH2CH3


2321.
NC(O)CH3
C(═O)N(CH3)—CH2—CO—OCH(CH3)2


2322.
NC(O)CH3
C(═O)N(CH3)—CH2—CO—OCH2CH2CH2CH3


2323.
NC(O)CH3
C(═O)N(CH3)—CH2—CO—OCH(CH3)CH2CH3


2324.
NC(O)CH3
C(═O)N(CH3)—CH2—CO—OCH2CH(CH3)2


2325.
NC(O)CH3
C(═O)N(CH3)—CH2—CO—OC(CH3)3


2326.
NC(O)CH3
C(═O)N(CH3)-A-1


2327.
NC(O)CH3
C(═O)N(CH3)-A-2


2328.
NC(O)CH3
C(═O)N(CH3)-A-3


2329.
NC(O)CH3
C(═O)N(CH3)-A-4


2330.
NC(O)CH3
C(═O)N(CH3)-A-5


2331.
NC(O)CH3
C(═O)N(CH3)-A-6


2332.
NC(O)CH3
C(═O)N(CH3)-A-7


2333.
NC(O)CH3
C(═O)N(CH3)-A-8


2334.
NC(O)CH3
C(═O)N(CH3)-A-9


2335.
NC(O)CH3
C(═O)N(CH3)-A-10


2336.
NC(O)CH3
C(═O)N(CH3)-A-11


2337.
NC(O)CH3
C(═O)N(CH3)-A-12


2338.
NC(O)CH3
C(═O)N(CH3)-A-13


2339.
NC(O)CH3
C(═O)N(CH3)-A-14


2340.
NC(O)CH3
C(═O)N(CH3)-A-15


2341.
NC(O)CH3
C(═O)N(CH3)-A-16


2342.
NC(O)CH3
C(═O)N(CH3)-A-17


2343.
NC(O)CH3
C(═O)N(CH3)-A-18


2344.
NC(O)CH3
C(═O)N(CH3)-A-19


2345.
NC(O)CH3
C(═O)N(CH3)-A-20


2346.
NC(O)CH3
C(═O)N(CH3)-A-21


2347.
NC(O)CH3
C(═O)N(CH3)-A-22


2348.
NC(O)CH3
C(═O)N(CH3)-A-23


2349.
NC(O)CH3
C(═O)N(CH3)-A-24


2350.
NC(O)CH3
C(═O)N(CH3)-A-25


2351.
NC(O)CH3
C(═O)N(CH3)-A-26


2352.
NC(O)CH3
C(═O)N(CH3)-A-27


2353.
NC(O)CH3
C(═O)N(CH3)-A-28


2354.
NC(O)CH3
C(═O)N(CH3)-A-29


2355.
NC(O)CH3
C(═O)N(CH3)-A-30


2356.
NC(O)CH3
C(═O)N(CH3)-A-31


2357.
NC(O)CH3
C(═O)N(CH3)-A-32


2358.
NC(O)CH3
C(═O)N(CH3)-A-33


2359.
NC(O)CH3
C(═O)N(CH3)—CH2-A-1


2360.
NC(O)CH3
C(═O)N(CH3)—CH2-A-2


2361.
NC(O)CH3
C(═O)N(CH3)—CH2-A-3


2362.
NC(O)CH3
C(═O)N(CH3)—CH2-A-4


2363.
NC(O)CH3
C(═O)N(CH3)—CH2-A-5


2364.
NC(O)CH3
C(═O)N(CH3)—CH2-A-6


2365.
NC(O)CH3
C(═O)N(CH3)—CH2-A-7


2366.
NC(O)CH3
C(═O)N(CH3)—CH2-A-8


2367.
NC(O)CH3
C(═O)N(CH3)—CH2-A-9


2368.
NC(O)CH3
C(═O)N(CH3)—CH2-A-10


2369.
NC(O)CH3
C(═O)N(CH3)—CH2-A-11


2370.
NC(O)CH3
C(═O)N(CH3)—CH2-A-12


2371.
NC(O)CH3
C(═O)N(CH3)—CH2-A-13


2372.
NC(O)CH3
C(═O)N(CH3)—CH2-A-14


2373.
NC(O)CH3
C(═O)N(CH3)—CH2-A-15


2374.
NC(O)CH3
C(═O)N(CH3)—CH2-A-16


2375.
NC(O)CH3
C(═O)N(CH3)—CH2-A-17


2376.
NC(O)CH3
C(═O)N(CH3)—CH2-A-18


2377.
NC(O)CH3
C(═O)N(CH3)—CH2-A-19


2378.
NC(O)CH3
C(═O)N(CH3)—CH2-A-20


2379.
NC(O)CH3
C(═O)N(CH3)—CH2-A-21


2380.
NC(O)CH3
C(═O)N(CH3)—CH2-A-22


2381.
NC(O)CH3
C(═O)N(CH3)—CH2-A-23


2382.
NC(O)CH3
C(═O)N(CH3)—CH2-A-24


2383.
NC(O)CH3
C(═O)N(CH3)—CH2-A-25


2384.
NC(O)CH3
C(═O)N(CH3)—CH2-A-26


2385.
NC(O)CH3
C(═O)N(CH3)—CH2-A-27


2386.
NC(O)CH3
C(═O)N(CH3)—CH2-A-28


2387.
NC(O)CH3
C(═O)N(CH3)—CH2-A-29


2388.
NC(O)CH3
C(═O)N(CH3)—CH2-A-30


2389.
NC(O)CH3
C(═O)N(CH3)—CH2-A-31


2390.
NC(O)CH3
C(═O)N(CH3)—CH2-A-32


2391.
NC(O)CH3
C(═O)N(CH3)—CH2-A-33


2392.
NC(O)CH3
C(═O)N(CH3)—SO2—CH3


2393.
NC(O)CH3
C(═O)N(CH3)—SO2—CF3


2394.
NC(O)CH3
C(═O)N(CH3)—SO2—CH2CH3


2395.
NC(O)CH3
C(═O)N(CH3)—SO2—CH2CF3


2396.
NC(O)CH3
C(═O)N(CH3)—SO2—CH2CH2CH3


2397.
NC(O)CH3
C(═O)N(CH3)—SO2—CH2CH2CF3


2398.
NC(O)CH3
C(═O)N(CH3)—SO2—CH2CF2CF3


2399.
NC(O)CH3
C(═O)N(CH3)—SO2—CH(CH3)2


2400.
NC(O)CH3
C(═O)N(CH3)—SO2—CH(CF3)2


2401.
NC(O)CH3
C(═O)NH—SO2—NH2


2402.
NC(O)CH3
C(═O)NH—SO2—NHCH3


2403.
NC(O)CH3
C(═O)NH—SO2—N(CH3)2


2404.
NC(O)CH3
C(═O)NH—SO2—NHCF3


2405.
NC(O)CH3
C(═O)NH—SO2—N(CF3)2


2406.
NC(O)CH3
C(═O)NH—SO2—NHCH2CH3


2407.
NC(O)CH3
C(═O)NH—SO2—N(CH2CH3)2


2408.
NC(O)CH3
C(═O)NH—SO2—NHCH2CF3


2409.
NC(O)CH3
C(═O)NH—SO2—N(CH2CF3)2


2410.
NC(O)CH3
C(═O)NH—SO2—N(CH3)CH2CH3


2411.
NC(O)CH3
C(═O)NH—SO2—N(CH3)CH2CF3


2412.
NC(O)CH3
C(═O)NH—SO2—N(CF3)CH2CH3


2413.
NC(O)CH3
C(═O)NH—SO2—NHCH2CH2CH3


2414.
NC(O)CH3
C(═O)NH—SO2—N(CH2CH2CH3)2


2415.
NC(O)CH3
C(═O)NH—SO2—NHCH2CH2CF3


2416.
NC(O)CH3
C(═O)NH—SO2—N(CH2CH2CF3)2


2417.
NC(O)CH3
C(═O)NH—SO2—N(CH3)CH2CH2CH3


2418.
NC(O)CH3
C(═O)NH—SO2—N(CH3)CH2CH2CF3


2419.
NC(O)CH3
C(═O)NH—SO2—N(CF3)CH2CH2CH3


2420.
NC(O)CH3
C(═O)NH—SO2—NHCH(CH3)2


2421.
NC(O)CH3
C(═O)NH—SO2—NHCH(CF3)2


2422.
NC(O)CH3
C(═O)NH—SO2—N(CH3)CH(CH3)2


2423.
NC(O)CH3
C(═O)NH—SO2—N(CH3)CH(CF3)2


2424.
NC(O)CH3
C(═O)NH—SO2—N(CF3)CH(CH3)2


2425.
NC(O)CH3
C(═O)NH—SO2—NHCH2CH2CH2CH3


2426.
NC(O)CH3
C(═O)NH—SO2—N(CH2CH2CH2CH3)2


2427.
NC(O)CH3
C(═O)NH—SO2—N(CH3)CH2CH2CH2CH3


2428.
NC(O)CH3
C(═O)N(CH3)—SO2—NH2


2429.
NC(O)CH3
C(═O)N(CH3)—SO2—NHCH3


2430.
NC(O)CH3
C(═O)N(CH3)—SO2—N(CH3)2


2431.
NC(O)CH3
C(═O)N(CH3)—SO2—NHCF3


2432.
NC(O)CH3
C(═O)N(CH3)—SO2—N(CF3)2


2433.
NC(O)CH3
C(═O)N(CH3)—SO2—NHCH2CH3


2434.
NC(O)CH3
C(═O)N(CH3)—SO2—N(CH2CH3)2


2435.
NC(O)CH3
C(═O)N(CH3)—SO2—NHCH2CF3


2436.
NC(O)CH3
C(═O)N(CH3)—SO2—N(CH2CF3)2


2437.
NC(O)CH3
C(═O)N(CH3)—SO2—N(CH3)CH2CH3


2438.
NC(O)CH3
C(═O)N(CH3)—SO2—N(CH3)CH2CF3


2439.
NC(O)CH3
C(═O)N(CH3)—SO2—N(CF3)CH2CH3


2440.
NC(O)CH3
C(═O)N(CH3)—SO2—NHCH2CH2CH3


2441.
NC(O)CH3
C(═O)N(CH3)—SO2—N(CH2CH2CH3)2


2442.
NC(O)CH3
C(═O)N(CH3)—SO2—NHCH2CH2CF3


2443.
NC(O)CH3
C(═O)N(CH3)—SO2—N(CH2CH2CF3)2


2444.
NC(O)CH3
C(═O)N(CH3)—SO2—N(CH3)CH2CH2CH3


2445.
NC(O)CH3
C(═O)N(CH3)—SO2—N(CH3)CH2CH2CF3


2446.
NC(O)CH3
C(═O)N(CH3)—SO2—N(CF3)CH2CH2CH3


2447.
NC(O)CH3
C(═O)N(CH3)—SO2—NHCH(CH3)2


2448.
NC(O)CH3
C(═O)N(CH3)—SO2—NHCH(CF3)2


2449.
NC(O)CH3
C(═O)N(CH3)—SO2—N(CH3)CH(CH3)2


2450.
NC(O)CH3
C(═O)N(CH3)—SO2—N(CH3)CH(CF3)2


2451.
NC(O)CH3
C(═O)N(CH3)—SO2—N(CF3)CH(CH3)2


2452.
NC(O)CH3
C(═O)N(CH3)—SO2—NHCH2CH2CH2CH3


2453.
NC(O)CH3
C(═O)N(CH3)—SO2—N(CH2CH2CH2CH3)2


2454.
NC(O)CH3
C(═O)N(CH3)—SO2—N(CH3)CH2CH2CH2CH3


2455.
NC(O)CH3
C(═O)—N═CHOCH3


2456.
NC(O)CH3
C(═O)—N═CHOCH2CH3


2457.
NC(O)CH3
C(═O)—N═CHOCH2CH2CH3


2458.
NC(O)CH3
C(═O)—N═CHOCH(CH3)2


2459.
NC(O)CH3
C(═O)—N═CHOCF3


2460.
NC(O)CH3
C(═O)—N═CHOCH2CF3


2461.
NC(O)CH3
C(═O)—N═CHOCH2CH2CF3


2462.
NC(O)CH3
C(═O)—N═CHOCH(CF3)2


2463.
NC(O)CH3
C(═O)—N═CH—CO—OCH3


2464.
NC(O)CH3
C(═O)—N═CH—CO—OCH2CH3


2465.
NC(O)CH3
C(═O)—N═CH—CO—OCH2CH2CH3


2466.
NC(O)CH3
C(═O)—N═CH—CO—OCH(CH3)2


2467.
NC(O)CH3
C(═O)—N═CH—CO—OCF3


2468.
NC(O)CH3
C(═O)—N═CH—CO—OCH2CF3


2469.
NC(O)CH3
C(═O)—N═CH—CO—OCH2CH2CF3


2470.
NC(O)CH3
C(═O)—N═CH—CO—OCH(CF3)2


2471.
NC(O)CH3
C(═O)—N═CH—CO—NHCH3


2472.
NC(O)CH3
C(═O)—N═CH—CO—N(CH3)2


2473.
NC(O)CH3
C(═O)—N═CH—CO—NHCH2CH3


2474.
NC(O)CH3
C(═O)—N═CH—CO—N(CH2CH3)2


2475.
NC(O)CH3
C(═O)—N═CH—CO—N(CH3)CH2CH3


2476.
NC(O)CH3
C(═O)—N═CH—CO—NHCH2CH2CH3


2477.
NC(O)CH3
C(═O)—N═CH—CO—N(CH2CH2CH3)2


2478.
NC(O)CH3
C(═O)—N═CH—CO—N(CH3)CH2CH2CH3


2479.
NC(O)CH3
C(═O)—N═CH—CO—NHCH(CH3)2


2480.
NC(O)CH3
C(═O)—N═CH—CO—N(CH3)CH(CH3)2


2481.
NC(O)CH3
C(═O)—N═CH—CO—NHCF3


2482.
NC(O)CH3
C(═O)—N═CH—CO—N(CF3)2


2483.
NC(O)CH3
C(═O)—N═CH—CO—NHCH2CF3


2484.
NC(O)CH3
C(═O)—N═CH—CO—N(CH2CF3)2


2485.
NC(O)CH3
C(═O)—N═CH—CO—N(CH3)CH2CF3


2486.
NC(O)CH3
C(═O)—N═CH—CO—N(CF3)CH2CF3


2487.
NC(O)CH3
C(═O)—N═CH—CO—NHCH2CH2CF3


2488.
NC(O)CH3
C(═O)—N═CH—CO—N(CH2CH2CF3)2


2489.
NC(O)CH3
C(═O)—N═CH—CO—N(CH3)CH2CH2CF3


2490.
NC(O)CH3
C(═O)—N═CH—CO—N(CF3)CH2CH2CH3


2491.
NC(O)CH3
C(═O)—N═CH—CO—NHCH(CF3)2


2492.
NC(O)CH3
C(═O)—N═CH—CO—N(CH3)CH(CF3)2


2493.
NC(O)CH3
C(═O)—N═CH—CO—N(CF3)CH(CH3)2


2494.
NC(O)CH3
C(═S)NH2


2495.
NC(O)CH3
C(═S)NHCH3


2496.
NC(O)CH3
C(═S)N(CH3)2


2497.
NC(O)CH3
C(═S)NHCF3


2498.
NC(O)CH3
C(═S)N(CF3)2


2499.
NC(O)CH3
C(═S)NHCH2CH3


2500.
NC(O)CH3
C(═S)N(CH2CH3)2


2501.
NC(O)CH3
C(═S)(CH3)CH2CH3


2502.
NC(O)CH3
C(═S)NHCH2CF3


2503.
NC(O)CH3
C(═S)N(CH2CF3)2


2504.
NC(O)CH3
C(═S)N(CH3)CH2CF3


2505.
NC(O)CH3
C(═S)NHCH2CH2CH3


2506.
NC(O)CH3
C(═S)N(CH3)CH2CH2CH3


2507.
NC(O)CH3
C(═S)NHCH(CH3)2


2508.
NC(O)CH3
C(═S)NH(CH2)3CH3


2509.
NC(O)CH3
C(═S)N(CH3)—(CH2)3CH3


2510.
NC(O)CH3
C(═S)N[(CH2)3CH3]2


2511.
NC(O)CH3
C(═S)N(CH3)—CH2—C6H5


2512.
NC(O)CH3
C(═S)NH-propargyl


2513.
NC(O)CH3
C(═S)N(CH3)-propargyl


2514.
NC(O)CH3
C(═S)NH—CH2-4-Cl—C6H4


2515.
NC(O)CH3
C(═S)N(CH3)—CH2-4-Cl—C6H4


2516.
NC(O)CH3
C(═S)morpholin-4-yl


2517.
NC(O)CH3
C(═S)NH-3-thiolyl-1,1-dioxid


2518.
NC(O)CH3
C(═S)N(CH3)-3-thiolyl-1,1-dioxid


2519.
NC(O)CH3
C(═S)-azirid-1-yl


2520.
NC(O)CH3
C(═S)-pyrrolidin-1-yl


2521.
NC(O)CH3
C(═S)-piperidin-1-yl


2522.
NC(O)CH3
C(═S)-thiomorpholin-4-yl


2523.
NC(O)CH3
C(═S)NH—CH2CHF2


2524.
NC(O)CH3
C(═S)NH—CH2CH2CHF2


2525.
NC(O)CH3
C(═S)NH—CH2CH2CF3


2526.
NC(O)CH3
C(═S)NH-cyclopropyl


2527.
NC(O)CH3
C(═S)NH-cyclobutyl


2528.
NC(O)CH3
C(═S)NH-cyclopentyl


2529.
NC(O)CH3
C(═S)NH-cyclohexyl


2530.
NC(O)CH3
C(═S)NH—CH2-cyclopropyl


2531.
NC(O)CH3
C(═S)NH—CH2-cyclobutyl


2532.
NC(O)CH3
C(═S)NH—CH2-cyclopentyl


2533.
NC(O)CH3
C(═S)NH—CH2-cyclohexyl


2534.
NC(O)CH3
C(═S)NH—CN


2535.
NC(O)CH3
C(═S)NH—CH2—CN


2536.
NC(O)CH3
C(═S)NH—CH2—CH═CH2


2537.
NC(O)CH3
C(═S)NH—CH2—CH═C(Cl)2


2538.
NC(O)CH3
C(═S)NH—CH2—CH═CH-phenyl


2539.
NC(O)CH3
C(═S)NH—CH2—CH═CH-(4-Cl-phenyl)


2540.
NC(O)CH3
C(═S)NH—CH2—SCH3


2541.
NC(O)CH3
C(═S)NH—CH2—SCF3


2542.
NC(O)CH3
C(═S)NH—CH2—CH2—SCH3


2543.
NC(O)CH3
C(═S)NH—CH2—CH2—SCF3


2544.
NC(O)CH3
C(═S)NH—CH2—SO2—CH3


2545.
NC(O)CH3
C(═S)NH—CH2—SO2—CF3


2546.
NC(O)CH3
C(═S)NH—CH2—CH2—SO2—CH3


2547.
NC(O)CH3
C(═S)NH—CH2—CH2—SO2—CF3


2548.
NC(O)CH3
C(═S)NH—CH2—CO—NH2


2549.
NC(O)CH3
C(═S)NH—CH2—CO—NHCH3


2550.
NC(O)CH3
C(═S)NH—CH2—CO—N(CH3)2


2551.
NC(O)CH3
C(═S)NH—CH2—CO—NHCF3


2552.
NC(O)CH3
C(═S)NH—CH2—CO—N(CF3)2


2553.
NC(O)CH3
C(═S)NH—CH2—CO—NHCH2CH3


2554.
NC(O)CH3
C(═S)NH—CH2—CO—N(CH2CH3)2


2555.
NC(O)CH3
C(═S)NH—CH2—CO—NHCH2CF3


2556.
NC(O)CH3
C(═S)NH—CH2—CO—N(CH2CF3)2


2557.
NC(O)CH3
C(═S)NH—CH2—CO—NHCH2CH2CH3


2558.
NC(O)CH3
C(═S)NH—CH2—CO—N(CH2CH2CH3)2


2559.
NC(O)CH3
C(═S)NH—CH2—CO—NHCH2CH2CF3


2560.
NC(O)CH3
C(═S)NH—CH2—CO—N(CH2CH2CF3)2


2561.
NC(O)CH3
C(═S)NH—CH2—CO—NHCH(CH3)2


2562.
NC(O)CH3
C(═S)NH—CH2—CO—NHCH(CF3)2


2563.
NC(O)CH3
C(═S)NH—CH2—CO—NH-cyclopropyl


2564.
NC(O)CH3
C(═S)NH—CH2—CO—NH—CH2-cyclopropyl


2565.
NC(O)CH3
C(═S)NH—CH2—CO—OH


2566.
NC(O)CH3
C(═S)NH—CH2—CO—OCH3


2567.
NC(O)CH3
C(═S)NH—CH2—CO—OCF3


2568.
NC(O)CH3
C(═S)NH—CH2—CO—OCH2CH3


2569.
NC(O)CH3
C(═S)NH—CH2—CO—OCH2CF3


2570.
NC(O)CH3
C(═S)NH—CH2—CO—OCH2CH2CH3


2571.
NC(O)CH3
C(═S)NH—CH2—CO—OCH(CH3)2


2572.
NC(O)CH3
C(═S)NH—CH2—CO—OCH2CH2CH2CH3


2573.
NC(O)CH3
C(═S)NH—CH2—CO—OCH(CH3)CH2CH3


2574.
NC(O)CH3
C(═S)NH—CH2—CO—OCH2CH(CH3)2


2575.
NC(O)CH3
C(═S)NH—CH2—CO—OC(CH3)3


2576.
NC(O)CH3
C(═S)NH-A-1


2577.
NC(O)CH3
C(═S)NH-A-2


2578.
NC(O)CH3
C(═S)NH-A-3


2579.
NC(O)CH3
C(═S)NH-A-4


2580.
NC(O)CH3
C(═S)NH-A-5


2581.
NC(O)CH3
C(═S)NH-A-6


2582.
NC(O)CH3
C(═S)NH-A-7


2583.
NC(O)CH3
C(═S)NH-A-8


2584.
NC(O)CH3
C(═S)NH-A-9


2585.
NC(O)CH3
C(═S)NH-A-10


2586.
NC(O)CH3
C(═S)NH-A-11


2587.
NC(O)CH3
C(═S)NH-A-12


2588.
NC(O)CH3
C(═S)NH-A-13


2589.
NC(O)CH3
C(═S)NH-A-14


2590.
NC(O)CH3
C(═S)NH-A-15


2591.
NC(O)CH3
C(═S)NH-A-16


2592.
NC(O)CH3
C(═S)NH-A-17


2593.
NC(O)CH3
C(═S)NH-A-18


2594.
NC(O)CH3
C(═S)NH-A-19


2595.
NC(O)CH3
C(═S)NH-A-20


2596.
NC(O)CH3
C(═S)NH-A-21


2597.
NC(O)CH3
C(═S)NH-A-22


2598.
NC(O)CH3
C(═S)NH-A-23


2599.
NC(O)CH3
C(═S)NH-A-24


2600.
NC(O)CH3
C(═S)NH-A-25


2601.
NC(O)CH3
C(═S)NH-A-26


2602.
NC(O)CH3
C(═S)NH-A-27


2603.
NC(O)CH3
C(═S)NH-A-28


2604.
NC(O)CH3
C(═S)NH-A-29


2605.
NC(O)CH3
C(═S)NH-A-30


2606.
NC(O)CH3
C(═S)NH-A-31


2607.
NC(O)CH3
C(═S)NH-A-32


2608.
NC(O)CH3
C(═S)NH-A-33


2609.
NC(O)CH3
C(═S)NH—CH2-A-1


2610.
NC(O)CH3
C(═S)NH—CH2-A-2


2611.
NC(O)CH3
C(═S)NH—CH2-A-3


2612.
NC(O)CH3
C(═S)NH—CH2-A-4


2613.
NC(O)CH3
C(═S)NH—CH2-A-5


2614.
NC(O)CH3
C(═S)NH—CH2-A-6


2615.
NC(O)CH3
C(═S)NH—CH2-A-7


2616.
NC(O)CH3
C(═S)NH—CH2-A-8


2617.
NC(O)CH3
C(═S)NH—CH2-A-9


2618.
NC(O)CH3
C(═S)NH—CH2-A-10


2619.
NC(O)CH3
C(═S)NH—CH2-A-11


2620.
NC(O)CH3
C(═S)NH—CH2-A-12


2621.
NC(O)CH3
C(═S)NH—CH2-A-13


2622.
NC(O)CH3
C(═S)NH—CH2-A-14


2623.
NC(O)CH3
C(═S)NH—CH2-A-15


2624.
NC(O)CH3
C(═S)NH—CH2-A-16


2625.
NC(O)CH3
C(═S)NH—CH2-A-17


2626.
NC(O)CH3
C(═S)NH—CH2-A-18


2627.
NC(O)CH3
C(═S)NH—CH2-A-19


2628.
NC(O)CH3
C(═S)NH—CH2-A-20


2629.
NC(O)CH3
C(═S)NH—CH2-A-21


2630.
NC(O)CH3
C(═S)NH—CH2-A-22


2631.
NC(O)CH3
C(═S)NH—CH2-A-23


2632.
NC(O)CH3
C(═S)NH—CH2-A-24


2633.
NC(O)CH3
C(═S)NH—CH2-A-25


2634.
NC(O)CH3
C(═S)NH—CH2-A-26


2635.
NC(O)CH3
C(═S)NH—CH2-A-27


2636.
NC(O)CH3
C(═S)NH—CH2-A-28


2637.
NC(O)CH3
C(═S)NH—CH2-A-29


2638.
NC(O)CH3
C(═S)NH—CH2-A-30


2639.
NC(O)CH3
C(═S)NH—CH2-A-31


2640.
NC(O)CH3
C(═S)NH—CH2-A-32


2641.
NC(O)CH3
C(═S)NH—CH2-A-33


2642.
NC(O)CH3
C(═S)NH—SO2—CH3


2643.
NC(O)CH3
C(═S)NH—SO2—CF3


2644.
NC(O)CH3
C(═S)NH—SO2—CH2CH3


2645.
NC(O)CH3
C(═S)NH—SO2—CH2CF3


2646.
NC(O)CH3
C(═S)NH—SO2—CH2CH2CH3


2647.
NC(O)CH3
C(═S)NH—SO2—CH2CH2CF3


2648.
NC(O)CH3
C(═S)NH—SO2—CH2CF2CF3


2649.
NC(O)CH3
C(═S)NH—SO2—CH(CH3)2


2650.
NC(O)CH3
C(═S)NH—SO2—CH(CF3)2


2651.
NC(O)CH3
C(═S)N(CH3)—CH2CHF2


2652.
NC(O)CH3
C(═S)N(CH3)—CH2CH2CHF2


2653.
NC(O)CH3
C(═S)N(CH3)—CH2CH2CF3


2654.
NC(O)CH3
C(═S)N(CH3)-cyclopropyl


2655.
NC(O)CH3
C(═S)N(CH3)-cyclobutyl


2656.
NC(O)CH3
C(═S)N(CH3)-cyclopentyl


2657.
NC(O)CH3
C(═S)N(CH3)-cyclohexyl


2658.
NC(O)CH3
C(═S)N(CH3)—CH2-cyclopropyl


2659.
NC(O)CH3
C(═S)N(CH3)—CH2-cyclobutyl


2660.
NC(O)CH3
C(═S)N(CH3)—CH2-cyclopentyl


2661.
NC(O)CH3
C(═S)N(CH3)—CH2-cyclohexyl


2662.
NC(O)CH3
C(═S)N(CH3)—CN


2663.
NC(O)CH3
C(═S)N(CH3)—CH2—CN


2664.
NC(O)CH3
C(═S)N(CH3)—CH2—CH═CH2


2665.
NC(O)CH3
C(═S)N(CH3)—CH2—CH═C(Cl)2


2666.
NC(O)CH3
C(═S)N(CH3)—CH2—CH═CH-phenyl


2667.
NC(O)CH3
C(═S)N(CH3)—CH2—CH═CH-(4-Cl-phenyl)


2668.
NC(O)CH3
C(═S)N(CH3)—CH2—SCH3


2669.
NC(O)CH3
C(═S)N(CH3)—CH2—SCF3


2670.
NC(O)CH3
C(═S)N(CH3)—CH2—CH2—SCH3


2671.
NC(O)CH3
C(═S)N(CH3)—CH2—CH2—SCF3


2672.
NC(O)CH3
C(═S)N(CH3)—CH2—SO2—CH3


2673.
NC(O)CH3
C(═S)N(CH3)—CH2—SO2—CF3


2674.
NC(O)CH3
C(═S)N(CH3)—CH2—CH2—SO2—CH3


2675.
NC(O)CH3
C(═S)N(CH3)—CH2—CH2—SO2—CF3


2676.
NC(O)CH3
C(═S)N(CH3)—CH2—CO—NH2


2677.
NC(O)CH3
C(═S)N(CH3)—CH2—CO—NHCH3


2678.
NC(O)CH3
C(═S)N(CH3)—CH2—CO—N(CH3)2


2679.
NC(O)CH3
C(═S)N(CH3)—CH2—CO—NHCF3


2680.
NC(O)CH3
C(═S)N(CH3)—CH2—CO—N(CF3)2


2681.
NC(O)CH3
C(═S)N(CH3)—CH2—CO—NHCH2CH3


2682.
NC(O)CH3
C(═S)N(CH3)—CH2—CO—N(CH2CH3)2


2683.
NC(O)CH3
C(═S)N(CH3)—CH2—CO—NHCH2CF3


2684.
NC(O)CH3
C(═S)N(CH3)—CH2—CO—N(CH2CF3)2


2685.
NC(O)CH3
C(═S)N(CH3)—CH2—CO—NHCH2CH2CH3


2686.
NC(O)CH3
C(═S)N(CH3)—CH2—CO—N(CH2CH2CH3)2


2687.
NC(O)CH3
C(═S)N(CH3)—CH2—CO—NHCH2CH2CF3


2688.
NC(O)CH3
C(═S)N(CH3)—CH2—CO—N(CH2CH2CF3)2


2689.
NC(O)CH3
C(═S)N(CH3)—CH2—CO—NHCH(CH3)2


2690.
NC(O)CH3
C(═S)N(CH3)—CH2—CO—NHCH(CF3)2


2691.
NC(O)CH3
C(═S)N(CH3)—CH2—CO—NH-cyclopropyl


2692.
NC(O)CH3
C(═S)N(CH3)—CH2—CO—NH—CH2-cyclopropyl


2693.
NC(O)CH3
C(═S)N(CH3)—CH2—CO—OH


2694.
NC(O)CH3
C(═S)N(CH3)—CH2—CO—OCH3


2695.
NC(O)CH3
C(═S)N(CH3)—CH2—CO—OCF3


2696.
NC(O)CH3
C(═S)N(CH3)—CH2—CO—OCH2CH3


2697.
NC(O)CH3
C(═S)N(CH3)—CH2—CO—OCH2CF3


2698.
NC(O)CH3
C(═S)N(CH3)—CH2—CO—OCH2CH2CH3


2699.
NC(O)CH3
C(═S)N(CH3)—CH2—CO—OCH(CH3)2


2700.
NC(O)CH3
C(═S)N(CH3)—CH2—CO—OCH2CH2CH2CH3


2701.
NC(O)CH3
C(═S)N(CH3)—CH2—CO—OCH(CH3)CH2CH3


2702.
NC(O)CH3
C(═S)N(CH3)—CH2—CO—OCH2CH(CH3)2


2703.
NC(O)CH3
C(═S)N(CH3)—CH2—CO—OC(CH3)3


2704.
NC(O)CH3
C(═S)N(CH3)-A-1


2705.
NC(O)CH3
C(═S)N(CH3)-A-2


2706.
NC(O)CH3
C(═S)N(CH3)-A-3


2707.
NC(O)CH3
C(═S)N(CH3)-A-4


2708.
NC(O)CH3
C(═S)N(CH3)-A-5


2709.
NC(O)CH3
C(═S)N(CH3)-A-6


2710.
NC(O)CH3
C(═S)N(CH3)-A-7


2711.
NC(O)CH3
C(═S)N(CH3)-A-8


2712.
NC(O)CH3
C(═S)N(CH3)-A-9


2713.
NC(O)CH3
C(═S)N(CH3)-A-10


2714.
NC(O)CH3
C(═S)N(CH3)-A-11


2715.
NC(O)CH3
C(═S)N(CH3)-A-12


2716.
NC(O)CH3
C(═S)N(CH3)-A-13


2717.
NC(O)CH3
C(═S)N(CH3)-A-14


2718.
NC(O)CH3
C(═S)N(CH3)-A-15


2719.
NC(O)CH3
C(═S)N(CH3)-A-16


2720.
NC(O)CH3
C(═S)N(CH3)-A-17


2721.
NC(O)CH3
C(═S)N(CH3)-A-18


2722.
NC(O)CH3
C(═S)N(CH3)-A-19


2723.
NC(O)CH3
C(═S)N(CH3)-A-20


2724.
NC(O)CH3
C(═S)N(CH3)-A-21


2725.
NC(O)CH3
C(═S)N(CH3)-A-22


2726.
NC(O)CH3
C(═S)N(CH3)-A-23


2727.
NC(O)CH3
C(═S)N(CH3)-A-24


2728.
NC(O)CH3
C(═S)N(CH3)-A-25


2729.
NC(O)CH3
C(═S)N(CH3)-A-26


2730.
NC(O)CH3
C(═S)N(CH3)-A-27


2731.
NC(O)CH3
C(═S)N(CH3)-A-28


2732.
NC(O)CH3
C(═S)N(CH3)-A-29


2733.
NC(O)CH3
C(═S)N(CH3)-A-30


2734.
NC(O)CH3
C(═S)N(CH3)-A-31


2735.
NC(O)CH3
C(═S)N(CH3)-A-32


2736.
NC(O)CH3
C(═S)N(CH3)-A-33


2737.
NC(O)CH3
C(═S)N(CH3)—CH2-A-1


2738.
NC(O)CH3
C(═S)N(CH3)—CH2-A-2


2739.
NC(O)CH3
C(═S)N(CH3)—CH2-A-3


2740.
NC(O)CH3
C(═S)N(CH3)—CH2-A-4


2741.
NC(O)CH3
C(═S)N(CH3)—CH2-A-5


2742.
NC(O)CH3
C(═S)N(CH3)—CH2-A-6


2743.
NC(O)CH3
C(═S)N(CH3)—CH2-A-7


2744.
NC(O)CH3
C(═S)N(CH3)—CH2-A-8


2745.
NC(O)CH3
C(═S)N(CH3)—CH2-A-9


2746.
NC(O)CH3
C(═S)N(CH3)—CH2-A-10


2747.
NC(O)CH3
C(═S)N(CH3)—CH2-A-11


2748.
NC(O)CH3
C(═S)N(CH3)—CH2-A-12


2749.
NC(O)CH3
C(═S)N(CH3)—CH2-A-13


2750.
NC(O)CH3
C(═S)N(CH3)—CH2-A-14


2751.
NC(O)CH3
C(═S)N(CH3)—CH2-A-15


2752.
NC(O)CH3
C(═S)N(CH3)—CH2-A-16


2753.
NC(O)CH3
C(═S)N(CH3)—CH2-A-17


2754.
NC(O)CH3
C(═S)N(CH3)—CH2-A-18


2755.
NC(O)CH3
C(═S)N(CH3)—CH2-A-19


2756.
NC(O)CH3
C(═S)N(CH3)—CH2-A-20


2757.
NC(O)CH3
C(═S)N(CH3)—CH2-A-21


2758.
NC(O)CH3
C(═S)N(CH3)—CH2-A-22


2759.
NC(O)CH3
C(═S)N(CH3)—CH2-A-23


2760.
NC(O)CH3
C(═S)N(CH3)—CH2-A-24


2761.
NC(O)CH3
C(═S)N(CH3)—CH2-A-25


2762.
NC(O)CH3
C(═S)N(CH3)—CH2-A-26


2763.
NC(O)CH3
C(═S)N(CH3)—CH2-A-27


2764.
NC(O)CH3
C(═S)N(CH3)—CH2-A-28


2765.
NC(O)CH3
C(═S)N(CH3)—CH2-A-29


2766.
NC(O)CH3
C(═S)N(CH3)—CH2-A-30


2767.
NC(O)CH3
C(═S)N(CH3)—CH2-A-31


2768.
NC(O)CH3
C(═S)N(CH3)—CH2-A-32


2769.
NC(O)CH3
C(═S)N(CH3)—CH2-A-33


2770.
NC(O)CH3
C(═S)N(CH3)—SO2—CH3


2771.
NC(O)CH3
C(═S)N(CH3)—SO2—CF3


2772.
NC(O)CH3
C(═S)N(CH3)—SO2—CH2CH3


2773.
NC(O)CH3
C(═S)N(CH3)—SO2—CH2CF3


2774.
NC(O)CH3
C(═S)N(CH3)—SO2—CH2CH2CH3


2775.
NC(O)CH3
C(═S)N(CH3)—SO2—CH2CH2CF3


2776.
NC(O)CH3
C(═S)N(CH3)—SO2—CH2CF2CF3


2777.
NC(O)CH3
C(═S)N(CH3)—SO2—CH(CH3)2


2778.
NC(O)CH3
C(═S)N(CH3)—SO2—CH(CF3)2


2779.
NC(O)CH3
C(═S)NH—SO2—NH2


2780.
NC(O)CH3
C(═S)NH—SO2—NHCH3


2781.
NC(O)CH3
C(═S)NH—SO2—N(CH3)2


2782.
NC(O)CH3
C(═S)NH—SO2—NHCF3


2783.
NC(O)CH3
C(═S)NH—SO2—N(CF3)2


2784.
NC(O)CH3
C(═S)NH—SO2—NHCH2CH3


2785.
NC(O)CH3
C(═S)NH—SO2—N(CH2CH3)2


2786.
NC(O)CH3
C(═S)NH—SO2—NHCH2CF3


2787.
NC(O)CH3
C(═S)NH—SO2—N(CH2CF3)2


2788.
NC(O)CH3
C(═S)NH—SO2—N(CH3)CH2CH3


2789.
NC(O)CH3
C(═S)NH—SO2—N(CH3)CH2CF3


2790.
NC(O)CH3
C(═S)NH—SO2—N(CF3)CH2CH3


2791.
NC(O)CH3
C(═S)NH—SO2—NHCH2CH2CH3


2792.
NC(O)CH3
C(═S)NH—SO2—N(CH2CH2CH3)2


2793.
NC(O)CH3
C(═S)NH—SO2—NHCH2CH2CF3


2794.
NC(O)CH3
C(═S)NH—SO2—N(CH2CH2CF3)2


2795.
NC(O)CH3
C(═S)NH—SO2—N(CH3)CH2CH2CH3


2796.
NC(O)CH3
C(═S)NH—SO2—N(CH3)CH2CH2CF3


2797.
NC(O)CH3
C(═S)NH—SO2—N(CF3)CH2CH2CH3


2798.
NC(O)CH3
C(═S)NH—SO2—NHCH(CH3)2


2799.
NC(O)CH3
C(═S)NH—SO2—NHCH(CF3)2


2800.
NC(O)CH3
C(═S)NH—SO2—N(CH3)CH(CH3)2


2801.
NC(O)CH3
C(═S)NH—SO2—N(CH3)CH(CF3)2


2802.
NC(O)CH3
C(═S)NH—SO2—N(CF3)CH(CH3)2


2803.
NC(O)CH3
C(═S)NH—SO2—NHCH2CH2CH2CH3


2804.
NC(O)CH3
C(═S)NH—SO2—N(CH2CH2CH2CH3)2


2805.
NC(O)CH3
C(═S)NH—SO2—N(CH3)CH2CH2CH2CH3


2806.
NC(O)CH3
C(═S)N(CH3)—SO2—NH2


2807.
NC(O)CH3
C(═S)N(CH3)—SO2—NHCH3


2808.
NC(O)CH3
C(═S)N(CH3)—SO2—N(CH3)2


2809.
NC(O)CH3
C(═S)N(CH3)—SO2—NHCF3


2810.
NC(O)CH3
C(═S)N(CH3)—SO2—N(CF3)2


2811.
NC(O)CH3
C(═S)N(CH3)—SO2—NHCH2CH3


2812.
NC(O)CH3
C(═S)N(CH3)—SO2—N(CH2CH3)2


2813.
NC(O)CH3
C(═S)N(CH3)—SO2—NHCH2CF3


2814.
NC(O)CH3
C(═S)N(CH3)—SO2—N(CH2CF3)2


2815.
NC(O)CH3
C(═S)N(CH3)—SO2—N(CH3)CH2CH3


2816.
NC(O)CH3
C(═S)N(CH3)—SO2—N(CH3)CH2CF3


2817.
NC(O)CH3
C(═S)N(CH3)—SO2—N(CF3)CH2CH3


2818.
NC(O)CH3
C(═S)N(CH3)—SO2—NHCH2CH2CH3


2819.
NC(O)CH3
C(═S)N(CH3)—SO2—N(CH2CH2CH3)2


2820.
NC(O)CH3
C(═S)N(CH3)—SO2—NHCH2CH2CF3


2821.
NC(O)CH3
C(═S)N(CH3)—SO2—N(CH2CH2CF3)2


2822.
NC(O)CH3
C(═S)N(CH3)—SO2—N(CH3)CH2CH2CH3


2823.
NC(O)CH3
C(═S)N(CH3)—SO2—N(CH3)CH2CH2CF3


2824.
NC(O)CH3
C(═S)N(CH3)—SO2—N(CF3)CH2CH2CH3


2825.
NC(O)CH3
C(═S)N(CH3)—SO2—NHCH(CH3)2


2826.
NC(O)CH3
C(═S)N(CH3)—SO2—NHCH(CF3)2


2827.
NC(O)CH3
C(═S)N(CH3)—SO2—N(CH3)CH(CH3)2


2828.
NC(O)CH3
C(═S)N(CH3)—SO2—N(CH3)CH(CF3)2


2829.
NC(O)CH3
C(═S)N(CH3)—SO2—N(CF3)CH(CH3)2


2830.
NC(O)CH3
C(═S)N(CH3)—SO2—NHCH2CH2CH2CH3


2831.
NC(O)CH3
C(═S)N(CH3)—SO2—N(CH2CH2CH2CH3)2


2832.
NC(O)CH3
C(═S)N(CH3)—SO2—N(CH3)CH2CH2CH2CH3


2833.
NC(O)CH3
C(═S)—N═CHOCH3


2834.
NC(O)CH3
C(═S)—N═CHOCH2CH3


2835.
NC(O)CH3
C(═S)—N═CHOCH2CH2CH3


2836.
NC(O)CH3
C(═S)—N═CHOCH(CH3)2


2837.
NC(O)CH3
C(═S)—N═CHOCF3


2838.
NC(O)CH3
C(═S)—N═CHOCH2CF3


2839.
NC(O)CH3
C(═S)—N═CHOCH2CH2CF3


2840.
NC(O)CH3
C(═S)—N═CHOCH(CF3)2


2841.
NC(O)CH3
C(═S)—N═CH—CO—OCH3


2842.
NC(O)CH3
C(═S)—N═CH—CO—OCH2CH3


2843.
NC(O)CH3
C(═S)—N═CH—CO—OCH2CH2CH3


2844.
NC(O)CH3
C(═S)—N═CH—CO—OCH(CH3)2


2845.
NC(O)CH3
C(═S)—N═CH—CO—OCF3


2846.
NC(O)CH3
C(═S)—N═CH—CO—OCH2CF3


2847.
NC(O)CH3
C(═S)—N═CH—CO—OCH2CH2CF3


2848.
NC(O)CH3
C(═S)—N═CH—CO—OCH(CF3)2


2849.
NC(O)CH3
C(═S)—N═CH—CO—NHCH3


2850.
NC(O)CH3
C(═S)—N═CH—CO—N(CH3)2


2851.
NC(O)CH3
C(═S)—N═CH—CO—NHCH2CH3


2852.
NC(O)CH3
C(═S)—N═CH—CO—N(CH2CH3)2


2853.
NC(O)CH3
C(═S)—N═CH—CO—N(CH3)CH2CH3


2854.
NC(O)CH3
C(═S)—N═CH—CO—NHCH2CH2CH3


2855.
NC(O)CH3
C(═S)—N═CH—CO—N(CH2CH2CH3)2


2856.
NC(O)CH3
C(═S)—N═CH—CO—N(CH3)CH2CH2CH3


2857.
NC(O)CH3
C(═S)—N═CH—CO—NHCH(CH3)2


2858.
NC(O)CH3
C(═S)—N═CH—CO—N(CH3)CH(CH3)2


2859.
NC(O)CH3
C(═S)—N═CH—CO—NHCF3


2860.
NC(O)CH3
C(═S)—N═CH—CO—N(CF3)2


2861.
NC(O)CH3
C(═S)—N═CH—CO—NHCH2CF3


2862.
NC(O)CH3
C(═S)—N═CH—CO—N(CH2CF3)2


2863.
NC(O)CH3
C(═S)—N═CH—CO—N(CH3)CH2CF3


2864.
NC(O)CH3
C(═S)—N═CH—CO—N(CF3)CH2CF3


2865.
NC(O)CH3
C(═S)—N═CH—CO—NHCH2CH2CF3


2866.
NC(O)CH3
C(═S)—N═CH—CO—N(CH2CH2CF3)2


2867.
NC(O)CH3
C(═S)—N═CH—CO—N(CH3)CH2CH2CF3


2868.
NC(O)CH3
C(═S)—N═CH—CO—N(CF3)CH2CH2CH3


2869.
NC(O)CH3
C(═S)—N═CH—CO—NHCH(CF3)2


2870.
NC(O)CH3
C(═S)—N═CH—CO—N(CH3)CH(CF3)2


2871.
NC(O)CH3
C(═S)—N═CH—CO—N(CF3)CH(CH3)2






cpropyl = cyclopropyl




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Among the above compounds of formulae I.1 to I.66, preference is given to compounds of formulae I.2 and I.8.


Compounds of formula I can be prepared by one or more of the following methods and variations as described in schemes 1 to 9. The variables A1, B1, X, Y, R1, R2, R4, R5, p and q are as defined above for formula I.


Compounds of formula I can be prepared by reaction of a styrene compound of formula 2 with a compound of formula II (Ra, Rb and Rc each independently represent optionally substituted alkyl, preferably C1-C12-alkyl, or optionally substituted phenyl and Rd represents hydrogen or is selected from optionally substituted alkyl, preferably C1-C12-alkyl, optionally substituted alkenyl, preferably C2-C12-alkenyl, optinally substituted alkynyl, preferably C2-C12-alkynyl or optionally substituted benzyl) as outlined in scheme 1. Such a procedure has been described, for example, in WO 2009/097992.




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The corresponding styrene compounds can be prepared as described in unpublished PCT/EP2010/055773.


Alternative preparation methods for compounds of formula I can be found in the aforementioned reference WO 2009/097992.


Compounds of formula I can also be prepared as outlined in scheme 2 by condensation of an hydroxamic acid derivative 3 with a Grignard reagent or an organolithium compound as for example described by Reutrakul et al, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, Wiley, Chichester, UK for the oximes and by Danko et al, Pest Management Science, 2006, 62, 229-236 for the hydrazones (Z is a leaving group like halogen, OR″ or SR″). The obtained ketoxime 4 is then converted into compounds of formula I by reaction with an alkylating agent as for example described by Huang et al, J. Org. Chem. 2008, 73, 4017-4026.




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Compounds of formula I can also be prepared as outlined in scheme 3 by reaction of an hydrazone 5 with a formylating agent to yield hydrazone 6 as for example described by Brehme et al, Zeitschrift f. Chemie, 1968, 8, 226-227.




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Compounds of formula I can also be prepared as outlined in scheme 4 by reaction of an aldehyde or ketone 7 with a hydroxylamine derivative as for example described by Stivers et al, WO 2006135763. Alternatively, compounds of formula I can also be prepared by reaction of an aldehyde or ketone 7 with a hydrazine derivative as for example described by Fattorusso et al, J. Med. Chem. 2008, 51, 1333-1343. Compounds of formula 7 can be prepared as described for example by Mihara et al, WO 2008/122375.




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Compounds of formula I can also be prepared as outlined in scheme 5 by reaction of an organo lithium reagent or a Grignard reagent 8 with an electrophile as for example described by Fujisawa et al, Chem. Lett. 1983, 51, 1537-1540 for nitro compounds as electrophile or by Ziegler et al, WO 95/20569 for hydroxamic acid derivatives. Hydrazone compounds of formula I can also be prepared as for example described by Benomar et al, J. Fluorine Chem. 1990, 50, 207-215 (J may be a metal, as for example Li, Na, K or MgX, SnX3; Z may be a leaving group like halogen, OR″ or SR″)




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Compounds of formula I can also be prepared as outlined in scheme 6 by reaction of a boronic acid 9 with an electrophile (e.g. a hydroxamic acid chloride) as for example described by Dolliver et al, Can. J. Chem. 2007, 85, 913-922. (M is a boronic acid derivative; Z may be a leaving group like halogen, OR″ or SR″). Compounds of formula 9 can be prepared as described for example in WO 2005/085216.




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Compounds of formula I can also be prepared as outlined in scheme 7 by reaction of an olefin of formula 10 with a nitrite as for example described by Sugamoto et al, Synlett, 1998, 1270-1272.




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Compounds of formula 7 can also be prepared as outlined in scheme 8 by reaction of an organometallic coumpound of formula 11 with a carboxylic acid derivative (Q may be a metal as for example ZnE, MgE, Li, Na, K, SnE3 with E being a leaving group such as halogen, or OR16 or S(O)nR16 and wherein n is 0-2); as described e.g. in WO 2008/156721 or by Dieter et al, Tetrahedron (2003), 59(7), 1083-1094. Compounds of formula 7 can also be prepared from secondary alcohols of formula 13 by oxidation, as for example described in US 2007265321. Compounds of formula 13 can be prepared by reaction of compounds of formula 11 with an aldehyde, as for example described by Yamagishi et al, Journal of Organic Chemistry (2009), 74(16), 6350-6353.




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The corresponding metal organyls of formula 11 can be prepared by a halogen-metal exchange reaction of halides of formula 12. The corresponding halides of formula 12 can be prepared as for example described in US 2007066617 or in unpublished PCT/EP2010/055773 (J may be a halogen as for example Cl, Br, I):


Compounds of formula 7 can also be prepared as outlined in scheme 9 by acidic hydrolysis of compounds of formula 14 [Z in this case equals R1], as for example described by Singh et al, European Journal of Organic Chemistry (2008), (32), 5446-5460.




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The corresponding aldehydes of formula 18 can be prepared from oximes of formula 14 by acidic hydrolysis (Z in this case equals H), as for example described by Lin et al, Chemistry—A European Journal (2009), 15(10), 2305-2309. Compounds of formula 14 can be prepared by diazotation of an amine of formula 15 and copper catalyzed reaction with a formoxime or a higher substituted oxime, as for example described by Philipp et al, Justus Liebigs Annalen der Chemie (1936), 523, 285-289 or by Woodward et al, Tetrahedron (1958), 2, 1-57 or in WO 2010/072781 or in WO 2010/072602. The corresponding compounds of formula 15 can be prepared according to WO 2007/125984.


Compounds of formula 18 can also be prepared by palladium catalyzed carbonylation of compounds of formula 16, as for example described by Banard et al, Organic Process Research & Development (2008), 12(4), 566-574. Compounds of formula 16 can also be prepared by reduction or a reduction/oxidation sequence of esters of formula 17, as for example described in WO 2007/017468 (reduction) or in WO 2006/128803 (reduction/oxidation sequence). Compounds of formula 17 can be prepared by carbonylation of compounds of formula 16, as for example described in WO 2005/085216.


If individual compounds cannot be prepared via the above-described routes, they can be prepared by derivatization of other compounds I or by customary modifications of the synthesis routes described.


The reaction mixtures are worked up in the customary manner, for example by mixing with water, separating the phases, and, if appropriate, purifying the crude products by chromatography, for example on alumina or silica gel. Some of the intermediates and end products may be obtained in the form of colorless or pale brown viscous oils, which are freed or purified from volatile components under reduced pressure and at moderately elevated temperature. If the intermediates and end products are obtained as solids, they may be purified by recrystallization or digestion.


Compound II is a valuable intermediate in the synthesis of compounds I. Thus the invention also relates to compounds of formula II




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wherein

  • Ra, Rb and Rc, independently of each other, are selected from C1-C12-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6, and phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10; and
  • Rd is selected from hydrogen, C1-C12-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6, C2-C12-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6, C2-C12-alkynyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6, and benzyl where the phenyl moiety may be substituted by 1, 2, 3, 4 or 5 radicals R10;
  • and A1, Y, R1, R2, R4 and p have one of the above-given general or, in particular, one of the above-given preferred meanings;
  • and the tautomers, stereoisomers and agriculturally or veterinarily acceptable salts thereof.


Tautomers of compounds II can for example occur if Rd is hydrogen. Such a tautomer, which is also a specific embodiment of compound II, can be represented by formula II′:




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Preferably, in compounds II and II′ Ra, Rb and Rc, independently of each other, are selected from C1-C4-alkyl and are specifically methyl.


Preferably, in compounds II Rd is selected from hydrogen, C1-C4-alkyl and C1-C4-haloalkyl.


Due to their excellent activity, the compounds of formula I may be used for controlling invertebrate pests.


Accordingly, the present invention also provides an agricultural composition comprising at least one compound of the formula I, as defined above, a stereoisomer thereof and/or at least one agriculturally acceptable salt thereof, and at least one inert liquid and/or solid agriculturally acceptable carrier.


The present invention also provides a veterinary composition comprising at least one compound of the formula I, as defined above, a stereoisomer thereof and/or at least one veterinarily acceptable salt thereof, and at least one inert liquid and/or solid veterinarily acceptable carrier.


Such compositions may contain a single active compound of formula I or a salt thereof or a mixture of several active compounds of formula I or their salts according to the present invention. The composition according to the present invention may comprise an individual isomer or mixtures of isomers as well as individual tautomers or mixtures of tautomers.


The present invention further relates to the use of a compound as defined above, of a stereoisomer and/or of an agriculturally or veterinarily acceptable salt thereof for combating invertebrate pests.


The present invention further relates to the use of a compound as defined above, of a stereoisomer and/or of a veterinarily acceptable salt thereof, for treating or protecting an animal from infestation or infection by invertebrate pests.


Moreover the present invention also provides a method for controlling invertebrate pests which method comprises treating the pests, their food supply, their habitat or their breeding ground or a plant, plant propagation material, soil, area, material or environment in which the pests are growing or may grow, or the materials, plants, plant propagation material, soils, surfaces or spaces to be protected from invertebrate pest attack or infestation with a pesticidally effective amount of at least one imine compound of the formula I as defined above, a stereoisomer thereof and/or at least one agriculturally acceptable salt thereof.


Preferably, the method of the invention serves for protecting plants or plant propagation material (such as seed) and the plant which grows therefrom from animal pest attack or infestation and comprises treating the plants or the plant propagation material (such as seed) with a pesticidally effective amount of a compound of the formula I or an agriculturally acceptable salt thereof as defined above or with a pesticidally effective amount of an agricultural composition as defined above and below. The method of the invention is not limited to the protection of the “substrate” (plant, plant propagation materials, soil material etc.) which has been treated according to the invention, but also has a preventive effect, thus, for example, according protection to a plant which grows from a treated plant propagation materials (such as seed), the plant itself not having been treated.


The invention furthermore relates to plant propagation material (such as seeds), comprising at least one compound of the formula I as defined above, a stereoisomer thereof and/or at least one agriculturally acceptable salt thereof.


The invention also provides a method for treating or protecting an animal from infestation or infection by invertebrate pests which comprises bringing the animal in contact with a pesticidally effective amount of at least one compound of the formula I as defined above, a stereoisomer thereof and/or at least one veterinarily acceptable salt thereof.


The compounds of the formula I and the pestidicidal compositions comprising them are effective agents for controlling arthropod pests and nematodes. Invertebrate pests controlled by the compounds of formula I include for example:

  • insects from the order of the lepidopterans (Lepidoptera), for example Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Chematobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholitha funebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Lamb-dina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocol-letis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseu-dotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris bras-sicae, Plathypena scabra, Plutella xylostella, Pseudoplusia includens, Rhyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni and Zeiraphera canadensis;
  • beetles (Coleoptera), for example Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12 punctata, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema oryzae, Ortiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus and Sitophilus granaria;
  • dipterans (Diptera), for example Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pipiens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipula oleracea and Tipula paludosa;
  • thrips (Thysanoptera), e.g. Dichromothrips corbetti, Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci;
  • hymenopterans (Hymenoptera), e.g. Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata and Solenopsis invicta;
  • heteropterans (Heteroptera), e.g. Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis and Thyanta perditor;
  • homopterans (Homoptera), e.g. Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis forbesi, Aphis pomi, Aphis gossypii, Aphis grossulariae, Aphis schneideri, Aphis spiraecola, Aphis sambuci, Acyrthosiphon pisum, Aulacorthum solani, Bemisia argentifolii, Brachycaudus cardui, Brachycaudus helichrysi, Brachycaudus persicae, Brachycaudus prunicola, Brevicoryne brassicae, Capitophorus horni, Cerosipha gossypii, Chaetosiphon fragaefolii, Cryptomyzus ribis, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Dysaphis plantaginea, Dysaphis pyri, Empoasca fabae, Hyalopterus pruni, Hyperomyzus lactucae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Melanaphis pyrarius, Metopolophium dirhodum, Myzodes persicae, Myzus ascalonicus, Myzus cerasi, Myzus persicae, Myzus varians, Nasonovia ribis-nigri, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Rhopalosiphum padi, Rhopalosiphum insertum, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Sitobion avenae, Sogatella furcifera Trialeurodes vaporariorum, Toxoptera aurantiiand, and Viteus vitifolii;
  • termites (Isoptera), e.g. Calotermes flavicollis, Leucotermes flavipes, Reticulitermes flavipes, Reticulitermes lucifugus und Termes natalensis;
  • orthopterans (Orthoptera), e.g. Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Periplaneta americana, Schistocerca americana, Schistocerca peregrina, Stauronotus maroccanus and Tachycines asynamorus;
  • Arachnoidea, such as arachnids (Acarina), e.g. of the families Argasidae, Ixodidae and Sarcoptidae, such as Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Dermacentor silvarum, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata, Otobius megnini, Dermanyssus gallinae, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, and Eriophyidae spp. such as Aculus schlechtendali, Phyllocoptrata oleivora and Eriophyes sheldoni; Tarsonemidae spp. such as Phytonemus pallidus and Polyphagotarsonemus latus; Tenuipalpidae spp. such as Brevipalpus phoenicis; Tetranychidae spp. such as Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae, Panonychus ulmi, Panonychus citri, and oligonychus pratensis;
  • Siphonatera, e.g. Xenopsylla cheopsis, Ceratophyllus spp;


The compositions and compounds of formula I are useful for the control of nematodes, especially plant parasitic nematodes such as root knot nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, and other Meloidogyne species;

  • cyst-forming nematodes, Globodera rostochiensis and other Globodera species; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterodera species; Seed gall nematodes, Anguina species; Stem and foliar nematodes, Aphelenchoides species; Sting nematodes, Belonolaimus longicaudatus and other Belonolaimus species; Pine nematodes, Bursaphelenchus xylophilus and other Bursaphelenchus species; Ring nematodes, Criconema species, Criconemella species, Criconemoides species, Mesocriconema species; Stem and bulb nematodes, Ditylenchus destructor, Ditylenchus dipsaci and other Ditylenchus species; Awl nematodes, Dolichodorus species; Spiral nematodes, Heliocotylenchus multicinctus and other Helicotylenchus species; Sheath and sheathoid nematodes, Hemicycliophora species and Hemicriconemoides species; Hirshmanniella species; Lance nematodes, Hoploaimus species; false rootknot nematodes, Nacobbus species; Needle nematodes, Longidorus elongatus and other Longidorus species; Pin nematodes, Paratylen-chus species; Lesion nematodes, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi and other Pratylenchus species; Burrowing nematodes, Radopholus similis and other Radopholus species; Reniform nematodes, Rotylenchus robustus and other Rotylenchus species; Scutellonema species; Stubby root nematodes, Trichodorus primitivus and other Trichodorus species, Paratrichodorus species; Stunt nematodes, Tylenchorhynchus claytoni, Tylenchorhynchus dubius and other Tylenchorhynchus species; Citrus nematodes, Tylenchulus species; Dagger nematodes, Xiphinema species; and other plant parasitic nematode species.


In a preferred embodiment of the invention the compounds of formula I are used for controlling insects or arachnids, in particular insects of the orders Lepidoptera, Coleoptera, Thysanoptera and Homoptera and arachnids of the order Acarina. The compounds of the formula I according to the present invention are particularly useful for controlling insects of the order Thysanoptera and Homoptera.


The compounds of formula I or the pesticidal compositions comprising them may be used to protect growing plants and crops from attack or infestation by invertebrate pests, especially insects, acaridae or arachnids by contacting the plant/crop with a pesticidally effective amount of compounds of formula I. The term “crop” refers both to growing and harvested crops.


The compounds of formula I can be converted into the customary formulations, for example solutions, emulsions, suspensions, dusts, powders, pastes and granules. The use form depends on the particular intended purpose; in each case, it should ensure a fine and even distribution of the compound according to the invention.


The formulations are prepared in a known manner (see e.g. for review U.S. Pat. No. 3,060,084, EP-A 707 445 (for liquid concentrates), Browning, “Agglomeration”, Chemical Engineering, Dec. 4, 1967, 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and et seq. WO 91/13546, U.S. Pat. Nos. 4,172,714, 4,144,050, 3,920,442, 5,180,587, 5,232,701, 5,208,030, GB 2,095,558, U.S. Pat. No. 3,299,566, Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989 and Mollet, H., Grubemann, A., Formulation technology, Wiley VCH Verlag GmbH, Weinheim (Germany), 2001, 2. D. A. Knowles, Chemistry and Technology of Agrochemical Formulations, Kluwer Academic Publishers, Dordrecht, 1998 (ISBN 0-7514-0443-8), for example by extending the active compound with auxiliaries suitable for the formulation of agrochemicals, such as solvents and/or carriers, if desired emulsifiers, surfactants and dispersants, preservatives, anti-foaming agents, anti-freezing agents, for seed treatment formulation also optionally colorants and/or binders and/or gelling agents.


Examples of suitable solvents are water, aromatic solvents (for example Solvesso products, xylene), paraffins (for example mineral oil fractions), alcohols (for example methanol, butanol, pentanol, benzyl alcohol), ketones (for example cyclohexanone, gamma-butyrolactone), pyrrolidones (N-methylpyrrolidone [NMP], N-octylpyrrolidone [NOP]), acetates (glycol diacetate), glycols, fatty acid dimethylamides, fatty acids and fatty acid esters. In principle, solvent mixtures may also be used.


Suitable emulsifiers are non-ionic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates).


Examples of dispersants are lignin-sulfite waste liquors and methylcellulose.


Suitable surfactants used are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, furthermore condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ether, tristearylphenyl polyglycol ether, alkylaryl polyether alcohols, alcohol and fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignosulfite waste liquors and methylcellulose.


Substances which are suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, highly polar solvents, for example dimethyl sulfoxide, N-methylpyrrolidone or water.


Also anti-freezing agents such as glycerin, ethylene glycol, propylene glycol and bactericides such as can be added to the formulation.


Suitable antifoaming agents are for example antifoaming agents based on silicon or magnesium stearate.


A suitable preservative is e.g. dichlorophen.


Seed treatment formulations may additionally comprise binders and optionally colorants.


Binders can be added to improve the adhesion of the active materials on the seeds after treatment. Suitable binders are block copolymers EO/PO surfactants but also polyvinylalcoholsl, polyvinylpyrrolidones, polyacrylates, polymethacrylates, polybute-nes, polyisobutylenes, polystyrene, polyethyleneamines, polyethyleneamides, polyethyleneimines (Lupasol®, Polymin®), polyethers, polyurethans, polyvinylacetate, tylose and copolymers derived from these polymers.


Optionally, also colorants can be included in the formulation. Suitable colorants or dyes for seed treatment formulations are Rhodamin B, C.I. Pigment Red 112, C.I. Solvent Red 1, pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1, pigment blue 80, pigment yellow 1, pigment yellow 13, pigment red 112, pigment red 48:2, pigment red 48:1, pigment red 57:1, pigment red 53:1, pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51, acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.


Examples of a gelling agent is carrageen (Satiagel®).


Powders, materials for spreading and dustable products can be prepared by mixing or concomitantly grinding the active substances with a solid carrier.


Granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds to solid carriers.


Examples of solid carriers are mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.


In general, the formulations comprise from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the active compound(s). In this case, the active compound(s) are employed in a purity of from 90% to 100% by weight, preferably 95% to 100% by weight (according to NMR spectrum).


For seed treatment purposes, respective formulations can be diluted 2-10 fold leading to concentrations in the ready to use preparations of 0.01 to 60% by weight active compound by weight, preferably 0.1 to 40% by weight.


The compounds of formula I can be used as such, in the form of their formulations or the use forms prepared therefrom, for example in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dustable products, materials for spreading, or granules, by means of spraying, atomizing, dusting, spreading or pouring. The use forms depend entirely on the intended purposes; they are intended to ensure in each case the finest possible distribution of the active compound(s) according to the invention.


Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetter, tackifier, dispersant or emulsifier.


However, it is also possible to prepare concentrates composed of active substance, wetter, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil, and such concentrates are suitable for dilution with water.


The active compound concentrations in the ready-to-use preparations can be varied within relatively wide ranges. In general, they are from 0.0001 to 10%, preferably from 0.01 to 1% per weight.


The active compound(s) may also be used successfully in the ultra-low-volume process (ULV), it being possible to apply formulations comprising over 95% by weight of active compound, or even to apply the active compound without additives.


The following are examples of formulations:

  • 1. Products for dilution with water for foliar applications. For seed treatment purposes, such products may be applied to the seed diluted or undiluted.


    A) Water-soluble Concentrates (SL, LS)


10 parts by weight of the active compound(s) are dissolved in 90 parts by weight of water or a water-soluble solvent. As an alternative, wetters or other auxiliaries are added. The active compound(s) dissolves upon dilution with water, whereby a formulation with 10% (w/w) of active compound(s) is obtained.


B) Dispersible Concentrates (DC)


20 parts by weight of the active compound(s) are dissolved in 70 parts by weight of cyclohexanone with addition of 10 parts by weight of a dispersant, for example polyvinylpyrrolidone. Dilution with water gives a dispersion, whereby a formulation with 20% (w/w) of active compound(s) is obtained.


C) Emulsifiable Concentrates (EC)


15 parts by weight of the active compound(s) are dissolved in 7 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution with water gives an emulsion, whereby a formulation with 15% (w/w) of active compound(s) is obtained.


D) Emulsions (EW, EO, ES)


25 parts by weight of the active compound(s) are dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). This mixture is introduced into 30 parts by weight of water by means of an emulsifier machine (e.g. Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion, whereby a formulation with 25% (w/w) of active compound(s) is obtained.


E) Suspensions (SC, OD, FS)


In an agitated ball mill, 20 parts by weight of the active compound(s) are comminuted with addition of 10 parts by weight of dispersants, wetters and 70 parts by weight of water or of an organic solvent to give a fine active compound(s) suspension. Dilution with water gives a stable suspension of the active compound(s), whereby a formulation with 20% (w/w) of active compound(s) is obtained.


F) Water-dispersible Granules and Water-soluble Granules (WG, SG)


50 parts by weight of the active compound(s) are ground finely with addition of 50 parts by weight of dispersants and wetters and made as water-dispersible or water-soluble granules by means of technical appliances (for example extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active compound(s), whereby a formulation with 50% (w/w) of active compound(s) is obtained.


G) Water-dispersible Powders and Water-soluble Powders (WP, SP, SS, WS)


75 parts by weight of the active compound(s) are ground in a rotor-stator mill with addition of 25 parts by weight of dispersants, wetters and silica gel. Dilution with water gives a stable dispersion or solution of the active compound(s), whereby a formulation with 75% (w/w) of active compound(s) is obtained.


H) Gel-Formulation (GF)


In an agitated ball mill, 20 parts by weight of the active compound(s) are comminuted with addition of 10 parts by weight of dispersants, 1 part by weight of a gelling agent wetters and 70 parts by weight of water or of an organic solvent to give a fine active compound(s) suspension. Dilution with water gives a stable suspension of the active compound(s), whereby a formulation with 20% (w/w) of active compound(s) is obtained.

  • 2. Products to be applied undiluted for foliar applications. For seed treatment purposes, such products may be applied to the seed diluted or undiluted.


    I) Dustable Powders (DP, DS)


5 parts by weight of the active compound(s) are ground finely and mixed intimately with 95 parts by weight of finely divided kaolin. This gives a dustable product having 5% (w/w) of active compound(s)


J) Granules (GR, FG, GG, MG)


0.5 parts by weight of the active compound(s) is ground finely and associated with 95.5 parts by weight of carriers, whereby a formulation with 0.5% (w/w) of active compound(s) is obtained. Current methods are extrusion, spray-drying or the fluidized bed. This gives granules to be applied undiluted for foliar use.


K) ULV Solutions (UL)


10 parts by weight of the active compound(s) are dissolved in 90 parts by weight of an organic solvent, for example xylene. This gives a product having 10% (w/w) of active compound(s), which is applied undiluted for foliar use.


The compounds of formula I are also suitable for the treatment of plant propagation materials (such as seed). Conventional seed treatment formulations include for example flowable concentrates FS, solutions LS, powders for dry treatment DS, water dispersible powders for slurry treatment WS, water-soluble powders SS and emulsion ES and EC and gel formulation GF. These formulations can be applied to the seed diluted or undiluted. Application to the seeds is carried out before sowing, either directly on the seeds or after having preger-minated the latter


In a preferred embodiment a FS formulation is used for seed treatment. Typcially, a FS formulation may comprise 1-800 g/l of active ingredient, 1-200 g/l Surfactant, 0 to 200 g/l antifreezing agent, 0 to 400 g/l of binder, 0 to 200 g/l of a pigment and up to 1 liter of a solvent, preferably water.


Other preferred FS formulations of compounds of formula I for seed treatment comprise from 0.5 to 80 wt % of the active ingredient, from 0.05 to 5 wt % of a wetter, from 0.5 to 15 wt % of a dispersing agent, from 0.1 to 5 wt % of a thickener, from 5 to 20 wt % of an anti-freeze agent, from 0.1 to 2 wt % of an anti-foam agent, from 1 to 20 wt % of a pigment and/or a dye, from 0 to 15 wt % of a sticker/adhesion agent, from 0 to 75 wt % of a filler/vehicle, and from 0.01 to 1 wt % of a preservative.


Various types of oils, wetters, adjuvants, herbicides, fungicides, other pesticides, or bactericides may be added to the active ingredients, if appropriate just immediately prior to use (tank mix). These agents usually are admixed with the agents according to the invention in a weight ratio of 1:10 to 10:1.


The compounds of formula I are effective through both contact (via soil, glass, wall, bed net, carpet, plant parts or animal parts), and ingestion (bait, or plant part).


For use against ants, termites, wasps, flies, mosquitos, crickets, or cockroaches, compounds of formula I are preferably used in a bait composition.


The bait can be a liquid, a solid or a semisolid preparation (e.g. a gel). Solid baits can be formed into various shapes and forms suitable to the respective application e.g. granules, blocks, sticks, disks. Liquid baits can be filled into various devices to ensure proper application, e.g. open containers, spray devices, droplet sources, or evaporation sources. Gels can be based on aqueous or oily matrices and can be formulated to particular necessities in terms of stickyness, moisture retention or aging characteristics.


The bait employed in the composition is a product, which is sufficiently attractive to incite insects such as ants, termites, wasps, flies, mosquitos, crickets etc. or cockroaches to eat it. The attractiveness can be manipulated by using feeding stimulants or sex pheromones. Food stimulants are chosen, for example, but not exclusively, from animal and/or plant proteins (meat-, fish- or blood meal, insect parts, egg yolk), from fats and oils of animal and/or plant origin, or mono-, oligo- or polyorganosaccharides, especially from sucrose, lactose, fructose, dextrose, glucose, starch, pectin or even molasses or honey. Fresh or decaying parts of fruits, crops, plants, animals, insects or specific parts thereof can also serve as a feeding stimulant. Sex pheromones are known to be more insect specific. Specific pheromones are described in the literature and are known to those skilled in the art.


Formulations of compounds of formula I as aerosols (e.g in spray cans), oil sprays or pump sprays are highly suitable for the non-professional user for controlling pests such as flies, fleas, ticks, mosquitos or cockroaches. Aerosol recipes are preferably composed of the active compound, solvents such as lower alcohols (e.g. methanol, ethanol, propanol, butanol), ketones (e.g. acetone, methyl ethyl ketone), paraffin hydrocarbons (e.g. kerosenes) having boiling ranges of approximately 50 to 250° C., dimethylfomaamide, N methylpyrrolidone, dimethyl sulphoxide, aromatic hydrocarbons such as toluene, xylene, water, furthermore auxiliaries such as emulsifiers such as sorbitol monooleate, oleyl ethoxylate having 3-7 mol of ethylene oxide, fatty alcohol ethoxylate, perfume oils such as ethereal oils, esters of medium fatty acids with lower alcohols, aromatic carbonyl compounds, if appropriate stabilizers such as sodium benzoate, amphoteric surfactants, lower epoxides, triethyl orthoformate and, if required, propellants such as propane, butane, nitrogen, compressed air, dimethyl ether, carbon dioxide, nitrous oxide, or mixtures of these gases.


The oil spray formulations differ from the aerosol recipes in that no propellants are used.


The compounds of formula I and their respective compositions can also be used in mosquito and fumigating coils, smoke cartridges, vaporizer plates or long-term vaporizers and also in moth papers, moth pads or other heat-independent vaporizer systems.


Methods to control infectious diseases transmitted by insects (e.g. malaria, dengue and yellow fever, lymphatic filariasis, and leishmaniasis) with compounds of formula I and their respective compositions also comprise treating surfaces of huts and houses, air spraying and impregnation of curtains, tents, clothing items, bed nets, tsetse-fly trap or the like. Insecticidal compositions for application to fibers, fabric, knitgoods, nonwovens, netting material or foils and tarpaulins preferably comprise a mixture including the insecticide, optionally a repellent and at least one binder. Suitable repellents for exam-pie are N,N-diethyl-meta-toluamide (DEET), N,N-diethylphenylacetamide (DEPA), 1-(3-cyclohexan-1-yl-carbonyl)-2-methylpiperine, (2-hydroxymethylcyclohexyl)acetic acid lactone, 2-ethyl-1,3-hexandiol, indalone, Methylneodecanamide (MNDA), a pyrethroid not used for insect control such as {(+/−)-3-allyl-2-methyl-4-oxocyclopent-2-(+)-enyl-(+)-trans-chrysantemate (Esbiothrin), a repellent derived from or identical with plant extracts like limonene, eugenol, (+)-Eucamalol (1), (−)-1-epi-eucamalol or crude plant extracts from plants like Eucalyptus maculata, Vitex rotundifolia, Cymbopogan martinii, Cymbopogan citratus (lemon grass), Cymopogan nartdus (citronella). Suitable binders are selected for example from polymers and copolymers of vinyl esters of aliphatic acids (such as such as vinyl acetate and vinyl versatate), acrylic and methacrylic esters of alcohols, such as butyl acrylate, 2-ethylhexylacrylate, and methyl acrylate, mono- and diethylenically unsaturated hydrocarbons, such as styrene, and aliphatic diens, such as butadiene.


The impregnation of curtains and bednets is done in general by dipping the textile material into emulsions or dispersions of the active compounds of formula I or spraying them onto the nets.


Methods which can be employed for treating the seed are, in principle, all suitable seed treatment and especially seed dressing techniques known in the art, such as seed coating (e.g. seed pelleting), seed dusting and seed imbibition (e.g. seed soaking). Here, “seed treatment” refers to all methods that bring seeds and the compounds of formula I into contact with each other, and “seed dressing” to methods of seed treatment which provide the seeds with an amount of the compounds of formula I, i.e. which generate a seed comprising the compound of formula I. In principle, the treatment can be applied to the seed at any time from the harvest of the seed to the sowing of the seed. The seed can be treated immediately before, or during, the planting of the seed, for example using the “planter's box” method. However, the treatment may also be carried out several weeks or months, for example up to 12 months, before planting the seed, for example in the form of a seed dressing treatment, without a substantially reduced efficacy being observed.


Expediently, the treatment is applied to unsown seed. As used herein, the term “unsown seed” is meant to include seed at any period from the harvest of the seed to the sowing of the seed in the ground for the purpose of germination and growth of the plant.


Specifically, a procedure is followed in the treatment in which the seed is mixed, in a suitable device, for example a mixing device for solid or solid/liquid mixing partners, with the desired amount of seed treatment formulations, either as such or after previous dilution with water, until the composition is distributed uniformly on the seed. If appropriate, this is followed by a drying step.


The compounds of formula I or veterinarily acceptable salts thereof are in particular also suitable for being used for combating parasites in and on animals.


A further object of the present invention is therefore to provide new methods for controlling parasites in and on animals. Another object of the invention is to provide safer pesticides for animals. Another object of the invention is further to provide pesticides for animals that may be used in lower doses than existing pesticides. And another object of the invention is to provide pesticides for animals, which provide a long residual control of the parasites.


The invention also relates to compositions containing a parasiticidally effective amount of compounds of formula I or veterinarily acceptable salts thereof and an acceptable carrier, for combating parasites in and on animals.


The present invention also provides a method for treating, controlling, preventing and protecting animals against infestation and infection by parasites, which comprises orally, topically or parenterally administering or applying to the animals a parasiticidally effective amount of a compound of formula I or veterinarily ac-ceptable salts thereof or a composition comprising it.


The present invention also provides a non-therapeutic method for treating, controlling, preventing and protecting animals against infestation and infection by parasites, which comprises applying to a locus a parasiticidally effective amount of a compound of formula I or the enantiomers or veterinarily acceptable salts thereof or a composition comprising it.


The invention also provides a process for the preparation of a composition for treating, controlling, preventing or protecting animals against infestation or infection by parasites which comprises including a parasiticidally effective amount of a compound of formula I or the veterinarily acceptable salts thereof or a composition comprising it.


The invention relates further to the use of compounds of formula I for treating, controlling, preventing or protecting animals against infestation or infection by parasites.


The invention relates also to the use of a compound of formula I, or a composition comprising it, for the manufacture of a medicament for the therapeutic treatment of animals against infections or infestions by parasites.


Activity of compounds against agricultural pests does not suggest their suitability for control of endo- and ectoparasites in and on animals which requires, for example, low, nonemetic dosages in the case of oral application, metabolic compatibility with the animal, low toxicity, and a safe handling.


Surprisingly, it has been found that compounds of formula I are suitable for com-bating endo- and ectoparasites in and on animals.


Compounds of formula I or veterinarily acceptable salts thereof and compositions comprising them are preferably used for controlling and preventing infestations and infections animals including warm-blooded animals (including humans) and fish. They are for example suitable for controlling and preventing infestations and infections in mammals such as cattle, sheep, swine, camels, deer, horses, pigs, poultry, rabbits, goats, dogs and cats, water buffalo, donkeys, fallow deer and reindeer, and also in fur-bearing animals such as mink, chinchilla and raccoon, birds such as hens, geese, turkeys and ducks and fish such as fresh- and salt-water fish such as trout, carp and eels.


Compounds of formula I or veterinarily acceptable salts thereof and compositions comprising them are preferably used for controlling and preventing infestations and infections in domestic animals, such as dogs or cats.


Infestations in warm-blooded animals and fish include, but are not limited to, lice, biting lice, ticks, nasal bots, keds, biting flies, muscoid flies, flies, myiasitic fly larvae, chiggers, gnats, mosquitoes and fleas.


The compounds of formula I or veterinarily acceptable salts thereof and compositions comprising them are suitable for systemic and/or non-systemic control of ecto- and/or endoparasites. They are active against all or some stages of development.


The compounds of formula I are especially useful for combating ectoparasites.


The compounds of formula I are especially useful for combating endoparasites.


The compounds of formula I are especially useful for combating parasites of the following orders and species, respectively:

  • fleas (Siphonaptera), e.g. Ctenocephalides felis, Ctenocephalides canis, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus,
  • cockroaches (Blattaria—Blattodea), e.g. Blattella germanica, Blattella asahinae, Periplaneta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blatta orientalis,
  • flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes albopictus, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inornata, Culiseta melanura, Dermatobia hominis, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hypoderma lineata, Leptoconops torrens, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mansonia spp., Musca domestica, Muscina stabulans, Oestrus ovis, Phlebotomus argentipes, Psorophora columbiae, Psorophora discolor, Prosimulium mixtum, Sarcophaga haemorrhoidalis, Sarcophaga sp., Simulium vittatum, Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus similis,
  • lice (Phthiraptera), e.g. Pediculus humanus capitis, Pediculus humanus corporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus.
  • ticks and parasitic mites (Parasitiformes): ticks (Ixodida), e.g. Ixodes scapularis, Ixodes holocyclus, Ixodes pacificus, Rhiphicephalus sanguineus, Dermacentor andersoni, Dermacentor variabilis, Amblyomma americanum, Ambryomma maculatum, Ornithodorus hermsi, Ornithodorus turicata and parasitic mites (Mesostigmata), e.g. Ornithonyssus bacoti and Dermanyssus gallinae,
  • actinedida (Prostigmata) and Acaridida (Astigmata) e.g. Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., and Laminosioptes spp,
  • bugs (Heteropterida): Cimex lectularius, Cimex hemipterus, Reduvius senilis, Triatoma spp., Rhodnius ssp., Panstrongylus ssp. and Arilus critatus,
  • Anoplurida, e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., and Solenopotes spp,
  • Mallophagida (suborders Arnblycerina and Ischnocerina), e.g. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Trichodectes spp., and Felicola spp,


    Roundworms Nematoda:
  • Wipeworms and Trichinosis (Trichosyringida), e.g. Trichinellidae (Trichinella spp.), (Trichuridae) Trichuris spp., Capillaria spp,
  • Rhabditida, e.g. Rhabditis spp, Strongyloides spp., Helicephalobus spp,
  • Strongylida, e.g. Strongylus spp., Ancylostoma spp., Necator americanus, Bunostomum spp. (Hookworm), Trichostrongylus spp., Haemonchus contortus, Ostertagia spp., Cooperia spp., Nematodirus spp., Dictyocaulus spp., Cyathostoma spp., Oesophagostomum spp., Stephanurus dentatus, Ollulanus spp., Chabertia spp., Stepha-nurus dentatus, Syngamus trachea, Ancylostoma spp., Uncinaria spp., Globocephalus spp., Necator spp., Metastrongylus spp., Muellerius capillaris, Protostrongylus spp., Angiostrongylus spp., Parelaphostrongylus spp. Aleurostrongylus abstrusus, and Dioctophyma renale,
  • Intestinal roundworms (Ascaridida), e.g. Ascaris lumbricoides, Ascaris suum, Ascaridia galli, Parascaris equorum, Enterobius vermicularis (Threadworm), Toxocara canis, Toxascaris leonine, Skrjabinema spp., and Oxyuris equi,
  • Camallanida, e.g. Dracunculus medinensis (guinea worm)
  • Spirurida, e.g. Thelazia spp. Wuchereria spp., Brugia spp., Onchocerca spp., Dirofilari spp.a, Dipetalonema spp., Setaria spp., Elaeophora spp., Spirocerca lupi, and Habronema spp.,
  • Thorny headed worms (Acanthocephala), e.g. Acanthocephalus spp., Macracanthorhynchus hirudinaceus and Oncicola spp,


    Planarians (Plathelminthes):
  • Flukes (Trematoda), e.g. Faciola spp., Fascioloides magna, Paragonimus spp., Dicrocoelium spp., Fasciolopsis buski, Clonorchis sinensis, Schistosoma spp., Trichobilharzia spp., Alaria alata, Paragonimus spp., and Nanocyetes spp,
  • Cercomeromorpha, in particular Cestoda (Tapeworms), e.g. Diphyllobothrium spp., Tenia spp., Echinococcus spp., Dipylidium caninum, Multiceps spp., Hymenolepis spp., Mesocestoides spp., Vampirolepis spp., Moniezia spp., Anoplocephala spp., Sirometra spp., Anoplocephala spp., and Hymenolepis spp.


The compounds of formula I and compositions containing them are particularly useful for the control of pests from the orders Diptera, Siphonaptera and Ixodida.


Moreover, the use of compounds of formula I and compositions containing them for combating mosquitoes is especially preferred.


The use of the compounds of formula I and compositions containing them for combating flies is a further preferred embodiment of the present invention.


Furthermore, the use of the compounds of formula I and compositions containing them for combating fleas is especially preferred.


The use of the compounds of formula I and of the compositions containing them for combating ticks is a further preferred embodiment of the present invention.


The compounds of formula I also are especially useful for combating endoparasites (roundworms nematoda, thorny headed worms and planarians).


The compounds of formula I can be effective through both contact (via soil, glass, wall, bed net, carpet, blankets or animal parts) and ingestion (e.g. baits).


The present invention relates to the therapeutic and the non-therapeutic use of compounds of formula I for controlling and/or combating parasites in and/or on animals.


The compounds of formula I may be used to protect the animals from attack or infestation by parasites by contacting them with a parasitically effective amount of compounds of formula I. As such, “contacting” includes both direct contact (applying the compounds/compositions directly on the parasite, e.g. also at it's locus, and optionally also administrating the compounds/composition directly on the animal) and indirect contact (applying the compounds/compositions to the locus of the parasite).


The contact of the parasite through application to its locus is an example of a non-therapeutic use of compounds of formula I.


“Locus” as defined above means the habitat, food supply, breeding ground, area, material or environment in which a parasite is growing or may grow outside of the animal. The compounds of the invention can also be applied preventively to places at which occurrence of the pests or parasites is expected.


Administration to the animal can be carried out both prophylactically and therapeutically.


Administration of the active compounds is carried out directly or in the form of suitable preparations, orally, topically/dermally or parenterally.


For oral administration to warm-blooded animals, the compounds of formula I may be formulated as animal feeds, animal feed premixes, animal feed concentrates, pills, solutions, pastes, suspensions, drenches, gels, tablets, boluses and capsules. In addition, the compounds of formulae I may be administered to the animals in their drinking water. For oral administration, the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the compounds of formula I, preferably with 0.5 mg/kg to 100 mg/kg of animal body weight per day.


Alternatively, the compounds of formula I may be administered to animals parenterally, for example, by intraluminal, intramuscular, intravenous or subcutaneous injection. The compounds of formula I may be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection. Alternatively, the compounds of formula I may be formulated into an implant for subcutaneous administration. In addition the compounds of formula I may be transdermally administered to animals. For parenteral administration, the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the compounds of formula I.


The compounds of formula I may also be applied topically to the animals in the form of dips, dusts, powders, collars, medallions, sprays, shampoos, spot-on and pour-on formulations and in ointments or oil-in-water or water-in-oil emulsions. For topical application, dips and sprays usually contain 0.5 ppm to 5,000 ppm and preferably 1 ppm to 3,000 ppm of the compounds of formula I. In addition, the compounds of formula I may be formulated as ear tags for animals, particularly quadrupeds such as cattle and sheep.


Suitable Preparations are:




  • Solutions such as oral solutions, concentrates for oral administration after dilution, solutions for use on the skin or in body cavities, pouring-on formulations, gels;

  • Emulsions and suspensions for oral or dermal administration; semi-solid preparations;

  • Formulations in which the active compound is processed in an ointment base or in an oil-in-water or water-in-oil emulsion base;

  • Solid preparations such as powders, premixes or concentrates, granules, pellets, tablets, boluses, capsules; aerosols and inhalants, and active compound-containing shaped articles.



Compositions suitable for injection are prepared by dissolving the active ingredient in a suitable solvent and optionally adding further ingredients such as acids, bases, buffer salts, preservatives, and solubilizers. The solutions are filtered and filled sterile.


Suitable solvents are physiologically tolerable solvents such as water, alkanols such as ethanol, butanol, benzyl alcohol, glycerol, propylene glycol, polyethylene glycols, N-methylpyrrolidone, 2-pyrrolidone, and mixtures thereof.


The active compounds can optionally be dissolved in physiologically tolerable vegetable or synthetic oils which are suitable for injection.


Suitable solubilizers are solvents which promote the dissolution of the active compound in the main solvent or prevent its precipitation. Examples are polyvinylpyrrolidone, polyvinyl alcohol, polyoxyethylated castor oil, and polyoxyethylated sorbitan ester.


Suitable preservatives are benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid esters, and n-butanol.


Oral solutions are administered directly. Concentrates are administered orally after prior dilution to the use concentration. Oral solutions and concentrates are prepared according to the state of the art and as described above for injection solutions, sterile procedures not being necessary.


Solutions for use on the skin are trickled on, spread on, rubbed in, sprinkled on or sprayed on.


Solutions for use on the skin are prepared according to the state of the art and according to what is described above for injection solutions, sterile procedures not being necessary.


Further suitable solvents are polypropylene glycol, phenyl ethanol, phenoxy ethanol, ester such as ethyl or butyl acetate, benzyl benzoate, ethers such as alkyleneglycol alkylether, e.g. dipropylenglycol monomethylether, ketons such as acetone, methylethylketone, aromatic hydrocarbons, vegetable and synthetic oils, dimethylformamide, dimethylacetamide, transcutol, solketal, propylencarbonate, and mixtures thereof.


It may be advantageous to add thickeners during preparation. Suitable thickeners are inorganic thickeners such as bentonites, colloidal silicic acid, aluminium monostearate, organic thickeners such as cellulose derivatives, polyvinyl alcohols and their copolymers, acrylates and methacrylates.


Gels are applied to or spread on the skin or introduced into body cavities. Gels are prepared by treating solutions which have been prepared as described in the case of the injection solutions with sufficient thickener that a clear material having an ointmentlike consistency results. The thickeners employed are the thickeners given above.


Pour-on formulations are poured or sprayed onto limited areas of the skin, the active compound penetrating the skin and acting systemically.


Pour-on formulations are prepared by dissolving, suspending or emulsifying the active compound in suitable skin-compatible solvents or solvent mixtures. If appropriate, other auxiliaries such as colorants, bioabsorption-promoting substances, antioxidants, light stabilizers, adhesives are added.


Suitable solvents are water, alkanols, glycols, polyethylene glycols, polypropylene glycols, glycerol, aromatic alcohols such as benzyl alcohol, phenylethanol, phenoxyethanol, esters such as ethyl acetate, butyl acetate, benzyl benzoate, ethers such as alkylene glycol alkyl ethers such as dipropylene glycol monomethyl ether, diethylene glycol mono-butyl ether, ketones such as acetone, methyl ethyl ketone, cyclic carbonates such as propylene carbonate, ethylene carbonate, aromatic and/or aliphatic hydrocarbons, vegetable or synthetic oils, DMF, dimethylacetamide, n-alkylpyrrolidones such as methylpyrrolidone, n-butylpyrrolidone or n-octylpyrrolidone, N methylpyrrolidone, 2-pyrrolidone, 2,2-dimethyl-4-oxy-methylene-1,3-diox-olane and glycerol formal.


Suitable colorants are all colorants permitted for use on animals and which can be dissolved or suspended.


Suitable absorption-promoting substances are, for example, DMSO, spreading oils such as isopropyl myristate, dipropylene glycol pelargonate, silicone oils and copolymers thereof with polyethers, fatty acid esters, triglycerides, fatty alcohols.


Suitable antioxidants are sulfites or metabisulfites such as potassium metabisulfite, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole, tocopherol.


Suitable light stabilizers are, for example, novantisolic acid.


Suitable adhesives are, for example, cellulose derivatives, starch derivatives, polyacrylates, natural polymers such as alginates, gelatin.


Emulsions can be administered orally, dermally or as injections.


Emulsions are either of the water-in-oil type or of the oil-in-water type.


They are prepared by dissolving the active compound either in the hydrophobic or in the hydrophilic phase and homogenizing this with the solvent of the other phase with the aid of suitable emulsifiers and, if appropriate, other auxiliaries such as colorants, absorption-promoting substances, preservatives, antioxidants, light stabilizers, viscosity-enhancing substances.


Suitable Hydrophobic Phases (Oils) are:




  • liquid paraffins, silicone oils, natural vegetable oils such as sesame oil, almond oil, castor oil, synthetic triglycerides such as caprylic/capric biglyceride, triglyceride mixture with vegetable fatty acids of the chain length C8-C12 or other specially selected natural fatty acids, partial glyceride mixtures of saturated or unsaturated fatty acids possibly also containing hydroxyl groups, mono- and diglycerides of the C8-C10 fatty acids, fatty acid esters such as ethyl stearate, di-n-butyryl adipate, hexyl laurate, dipropylene glycol perlargonate, esters of a branched fatty acid of medium chain length with saturated fatty alcohols of chain length C16-C18, isopropyl myristate, isopropyl palmitate, caprylic/capric acid esters of saturated fatty alcohols of chain length C12-C18, isopropyl stearate, oleyl oleate, decyl oleate, ethyl oleate, ethyl lactate, waxy fatty acid esters such as synthetic duck coccygeal gland fat, dibutyl phthalate, diisopropyl adipate, and ester mixtures related to the latter, fatty alcohols such as isotridecyl alcohol, 2-octyldodecanol, cetylstearyl alcohol, oleyl alcohol, and fatty acids such as oleic acid and mixtures thereof.



Suitable hydrophilic phases are: water, alcohols such as propylene glycol, glycerol, sorbitol and mixtures thereof.


Suitable Emulsifiers are:




  • non-ionic surfactants, e.g. polyethoxylated castor oil, polyethoxylated sorbitan monooleate, sorbitan monostearate, glycerol monostearate, polyoxyethyl stearate, alkylphenol polyglycol ether;

  • ampholytic surfactants such as di-sodium N-lauryl-p-iminodipropionate or lecithin; anionic surfactants, such as sodium lauryl sulfate, fatty alcohol ether sulfates, mono/dialkyl polyglycol ether orthophosphoric acid ester monoethanolamine salt; cation-active surfactants, such as cetyltrimethylammonium chloride.



Suitable further auxiliaries are: substances which enhance the viscosity and stabilize the emulsion, such as carboxymethylcellulose, methylcellulose and other cellulose and starch derivatives, polyacrylates, alginates, gelatin, gum arabic, polyvinylpyrrolidone, polyvinyl alcohol, copolymers of methyl vinyl ether and maleic anhydride, polyethylene glycols, waxes, colloidal silicic acid or mixtures of the substances mentioned.


Suspensions can be administered orally or topically/dermally. They are prepared by suspending the active compound in a suspending agent, if appropriate with addition of other auxiliaries such as wetting agents, colorants, bioabsorption-promoting substances, preservatives, antioxidants, light stabilizers.


Liquid suspending agents are all homogeneous solvents and solvent mixtures.


Suitable wetting agents (dispersants) are the emulsifiers given above.


Other auxiliaries which may be mentioned are those given above.


Semi-solid preparations can be administered orally or topically/dermally. They differ from the suspensions and emulsions described above only by their higher viscosity.


For the production of solid preparations, the active compound is mixed with suitable excipients, if appropriate with addition of auxiliaries, and brought into the desired form.


Suitable excipients are all physiologically tolerable solid inert substances. Those used are inorganic and organic substances. Inorganic substances are, for example, sodium chloride, carbonates such as calcium carbonate, hydrogencarbonates, aluminium oxides, titanium oxide, silicic acids, argillaceous earths, precipitated or colloidal silica, or phosphates. Organic substances are, for example, sugar, cellulose, foodstuffs and feeds such as milk powder, animal meal, grain meals and shreds, starches.


Suitable auxiliaries are preservatives, antioxidants, and/or colorants which have been mentioned above.


Other suitable auxiliaries are lubricants and glidants such as magnesium stearate, stearic acid, talc, bentonites, disintegration-promoting substances such as starch or crosslinked polyvinylpyrrolidone, binders such as starch, gelatin or linear polyvinylpyrrolidone, and dry binders such as microcrystalline cellulose.


In general, “parasiticidally effective amount” means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The parasiticidally effective amount can vary for the various compounds/compositions used in the invention. A parasiticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired parasiticidal effect and duration, target species, mode of application, and the like.


The compositions which can be used in the invention can comprise generally from about 0.001 to 95% of the compounds of formula I.


Generally, it is favorable to apply the compounds of formula I in total amounts of 0.5 mg/kg to 100 mg/kg per day, preferably 1 mg/kg to 50 mg/kg per day.


Ready-to-use preparations contain the compounds acting against parasites, preferably ectoparasites, in concentrations of 10 ppm to 80 percent by weight, preferably from 0.1 to 65 percent by weight, more preferably from 1 to 50 percent by weight, most preferably from 5 to 40 percent by weight.


Preparations which are diluted before use contain the compounds acting against ectoparasites in concentrations of 0.5 to 90 percent by weight, preferably of 1 to 50 percent by weight.


Furthermore, the preparations comprise the compounds of formula I against endoparasites in concentrations of 10 ppm to 2 percent by weight, preferably of 0.05 to 0.9 percent by weight, very particularly preferably of 0.005 to 0.25 percent by weight.


In a preferred embodiment of the present invention, the compositions comprising the compounds of formula I are applied dermally/topically.


In a further preferred embodiment, the topical application is conducted in the form of compound-containing shaped articles such as collars, medallions, ear tags, bands for fixing at body parts, and adhesive strips and foils.


Generally, it is favorable to apply solid formulations which release compounds of formula I in total amounts of 10 mg/kg to 300 mg/kg, preferably 20 mg/kg to 200 mg/kg, most preferably 25 mg/kg to 160 mg/kg body weight of the treated animal in the course of three weeks.


For the preparation of the shaped articles, thermoplastic and flexible plastics as well as elastomers and thermoplastic elastomers are used. Suitable plastics and elastomers are polyvinyl resins, polyurethane, polyacrylate, epoxy resins, cellulose, cellulose derivatives, polyamides and polyester which are sufficiently compatible with the compounds of formula I. A detailed list of plastics and elastomers as well as preparation procedures for the shaped articles is given e.g. in WO 03/086075.


Compositions to be used according to this invention may also contain other active ingredients, for example other pesticides, insecticides, herbicides, fungicides, other pesticides, or bactericides, fertilizers such as ammonium nitrate, urea, potash, and superphosphate, phytotoxicants and plant growth regulators, safeners and nematicides. These additional ingredients may be used sequentially or in combination with the above-described compositions, if appropriate also added only immediately prior to use (tank mix). For example, the plant(s) may be sprayed with a composition of this invention either before or after being treated with other active ingredients.


These agents can be admixed with the agents used according to the invention in a weight ratio of 1:10 to 10:1. Mixing the compounds of formula I or the compositions comprising them in the use form as pesticides with other pesticides frequently results in a broader pesticidal spectrum of action.


The following list M of pesticides together with which the compounds according to the invention can be used and with which potential synergistic effects might be produced, is intended to illustrate the possible combinations, but not to impose any limitation:

  • M.1. Organo(thio)phosphate compounds: acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, 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, flupyrazophos, fosthiazate, heptenophos, 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;
  • M.2. Carbamate compounds: 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;
  • M.3. Pyrethroid compounds: acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zetacypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, metofluthrin, permethrin, phenothrin, prallethrin, profluthrin, pyrethrin (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tralomethrin, transfluthrin;
  • M.4. Juvenile hormone mimics: hydroprene, kinoprene, methoprene, fenoxycarb, pyriproxyfen;
  • M.5. Nicotinic receptor agonists/antagonists compounds: acetamiprid, bensultap, cartap hydrochloride, clothianidin, dinotefuran, imidacloprid, thiamethoxam, nitenpyram, nicotine, spinosad (allosteric agonist), spinetoram (allosteric agonist), thiacloprid, thiocyclam, thiosultap-sodium and AKD1022.
  • M.6. GABA gated chloride channel antagonist compounds: chlordane, endosulfan, gamma-HCH (lindane); ethiprole, fipronil, pyrafluprole, pyriprole
  • M.7. Chloride channel activators: abamectin, emamectin benzoate, milbemectin, lepimectin;
  • M.8. METI I compounds: fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, flufenerim, rotenone;
  • M.9. METI II and III compounds: acequinocyl, fluacyprim, hydramethylnon;
  • M.10. Uncouplers of oxidative phosphorylation: chlorfenapyr, DNOC;
  • M.11. Inhibitors of oxidative phosphorylation: azocyclotin, cyhexatin, diafenthiuron, fenbutatin oxide, propargite, tetradifon;
  • M.12. Moulting disruptors: cyromazine, chromafenozide, halofenozide, methoxyfenozide, tebufenozide;
  • M.13. Synergists: piperonyl butoxide, tribufos;
  • M.14. Sodium channel blocker compounds: indoxacarb, metaflumizone;
  • M.15. Fumigants: methyl bromide, chloropicrin sulfuryl fluoride;
  • M.16. Selective feeding blockers: crylotie, pymetrozine, flonicamid;
  • M.17. Mite growth inhibitors: clofentezine, hexythiazox, etoxazole;
  • M.18. Chitin synthesis inhibitors: buprofezin, bistrifluoron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron;
  • M.19. Lipid biosynthesis inhibitors: spirodiclofen, spiromesifen, spirotetramat;
  • M.20. Octapaminergic agonsits: amitraz;
  • M.21. Ryanodine receptor modulators: flubendiamide and the phtalamid compound (R)- , (S)-3-Chlor-N-1-{2-methyl-4-[1,2,2,2-tetrafluor-1-(trifluormethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamid (M21.1)
  • M.22. Isoxazoline compounds: 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-pyridin-2-ylmethyl-benzamide (M22.1), 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-N-(2,2,2-trifluoro-ethyl)-benzamide (M22.2), 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-N-[(2,2,2-trifluoro-ethylcarbamoyl)-methyl]-benzamide (M22.3), 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-naphthalene-1-carboxylic acid [(2,2,2-trifluoro-ethylcarbamoyl)-methyl]-amide (M22.4)4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-N-[(methoxyimino)methyl]-2-methylbenzamide (M22.5), 4-[5-(3-Chloro-5-trifluoromethylphenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-N-[(2,2,2-trifluoroethylcarbamoyl)-methyl]-benzamide (M22.6), 4-[5-(3-Chloro-5-trifluoromethyl-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-naphthalene-1-carboxylic acid [(2,2,2-trifluoro-ethylcarbamoyl)-methyl]-amide (M22.7) and 5-[5-(3,5-Dichloro-4-fluorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-[1,2,4]triazol-1-yl-benzonitrile (M22.8);
  • M.23. Anthranilamide compounds: chloranthraniliprole, cyantraniliprole, 5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid [4-cyano-2-(1-cyclopropyl-ethylcarbamoyl)-6-methyl-phenyl]-amide (M23.1), 5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid [2-chloro-4-cyano-6-(1-cyclopropyl-ethylcarbamoyl)-phenyl]-amide (M23.2), 5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid [2-bromo-4-cyano-6-(1-cyclopropyl-ethylcarbamoyl)-phenyl]-amide (M23.3), 5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid [2-bromo-4-chloro-6-(1-cyclopropyl-ethylcarbamoyl)-phenyl]-amide (M23.4), 5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid [2,4-dichloro-6-(1-cyclopropyl-ethylcarbamoyl)-phenyl]-amide (M23.5), 5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid [4-chloro-2-(1-cyclopropyl-ethylcarbamoyl)-6-methyl-phenyl]-amide (M23.6), N′-(2-{[5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-5-chloro-3-methyl-benzoyl)-hydrazinecarboxylic acid methyl ester (M23.7), N′-(2-{[5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-5-chloro-3-methyl-benzoyl)-N′-methyl-hydrazinecarboxylic acid methyl ester (M23.8), N′-(2-{[5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-5-chloro-3-methyl-benzoyl)-N,N′-dimethyl-hydrazinecarboxylic acid methyl ester (M23.9), N′-(3,5-Dibromo-2-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-benzoyl)-hydrazinecarboxylic acid methyl ester (M23.10), N′-(3,5-Dibromo-2-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-benzoyl)-N′-methyl-hydrazinecarboxylic acid methyl ester (M23.11) and N′-(3,5-Dibromo-2-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-benzoyl)-N,N′-dimethyl-hydrazinecarboxylic acid methyl ester (M23.12);
  • M.24. Malononitrile compounds: 2-(2,2,3,3,4,4,5,5-octafluoropentyl)-2-(3,3,3-trifluoropropyl)malononitrile (CF2H—CF2—CF2—CF2—CH2—C(CN)2—CH2—CH2—CF3) (M24.1) and 2-(2,2,3,3,4,4,5,5-octafluoropentyl)-2-(3,3,4,4,4-pentafluorobutyl)-malonodinitrile (CF2H—CF2—CF2—CF2—CH2—C(CN)2—CH2—CH2—CF2—CF3) (M24.2);
  • M.25. Microbial disruptors: Bacillus thuringiensis subsp. Israelensi, Bacillus sphaericus, Bacillus thuringiensis subsp. Aizawai, Bacillus thuringiensis subsp. Kurstaki, Bacillus thuringiensis subsp. Tenebrionis;
  • M.26. Aminofuranone compounds: 4-{[(6-Bromopyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-on (M26.1), 4-{[(6-Fluoropyrid-3-yl)methyl](2,2-difluoroethyl)amino}furan-2(5H)-on (M26.2), 4-{[(2-Chloro-1,3-thiazolo-5-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-on (M26.3), 4-{[(6-Chloropyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-on (M26.4), 4-{[(6-Chloropyrid-3-yl)methyl](2,2-difluoroethyl)amino}furan-2(5H)-on (M26.5), 4-{[(6-Chloro-5-fluoropyrid-3-yl)methyl](methyl)amino}furan-2(5H)-on (M26.6), 4-{[(5,6-Dichloropyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-on (M26.7), 4-{[(6-Chloro-5-fluoropyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-on (M26.8), 4-{[(6-Chloropyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-on (M26.9) and 4-{[(6-Chloropyrid-3-yl)methyl](methyl)amino}furan-2(5H)-on (M26.10);
  • M.27. Various compounds: aluminium phosphide, amidoflumet, benclothiaz, benzoximate, bifenazate, borax, bromopropylate, cyanide, cyenopyrafen, cyflumetofen, chinomethionate, dicofol, fluoroacetate, phosphine, pyridalyl, pyrifluquinazon, sulfur, organic sulfur compounds, tartar emetic, sulfoxaflor, N—R′-2,2-dihalo-1-R″cyclopropanecarboxamide-2-(2,6-dichloro-α,α,α-trifluoro-p-tolyl)hydrazone or N—R′-2,2-di(R′″)propionamide-2-(2,6-dichloro-α,α,α-trifluoro-p-tolyl)-hydrazone, wherein R′ is methyl or ethyl, halo is chloro or bromo, R″ is hydrogen or methyl and R′″ is methyl or ethyl, 4-But-2-ynyloxy-6-(3,5-dimethyl-piperidin-1-yl)-2-fluoro-pyrimidine (M27.1), Cyclopropaneacetic acid, 1,1′-[(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-4-[[(2-cyclopropylacetyl)oxy]methyl]-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-[2-hydroxy-4,6a,12b-trimethyl-11-oxo-9-(3-pyridinyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-3,6-diyl]ester (M27.2) and 8-(2-Cyclopropylmethoxy-4-trifIuoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1]octane (M27.3).


The commercially available compounds of the group M may be found in The Pesticide Manual, 13th Edition, British Crop Protection Council (2003) among other publications.


Paraoxon and their preparation have been described in Farm Chemicals Handbook, Volume 88, Meister Publishing Company, 2001. Flupyrazofos has been described in Pesticide Science 54, 1988, p. 237-243 and in U.S. Pat. No. 4,822,779. AKD 1022 and its preparation have been described in U.S. Pat. No. 6,300,348. The anthranilamides M23.1 to M23.6 have been described in WO 2008/72743 and WO 200872783, those M23.7 to M23.12 in WO2007/043677. The phthalamide M 21.1 is known from WO 2007/101540. The alkynylether compound M27.1 is described e.g. in JP 2006131529. Organic sulfur compounds have been described in WO 2007060839. The isoxazoline compounds M 22.1 to M 22.8 have been described in e.g. WO2005/085216, WO 2007/079162, WO 2007/026965, WO 2009/126668 and WO2009/051956. The aminofuranone compounds M 26.1 to M 26.10 have been described eg. in WO 2007/115644. The pyripyropene derivative M 27.2 has been described in WO 2008/66153 and WO 2008/108491. The pyridazin compound M 27.3 has been described in JP 2008/115155. Malononitrile compounds as those (M24.1) and (M24.2) have been described in WO 02/089579, WO 02/090320, WO 02/090321, WO 04/006677, WO 05/068423, WO 05/068432 and WO 05/063694.


The following list F of fungicides together with which the compounds according to the invention can be used and with which potential synergistic effects might be produced, is intended to illustrate the possible combinations, but not to impose any limitation:


F.I) Respiration Inhibitors




  • F.I-1) Inhibitors of complex III at Qo site (e.g. strobilurins) strobilurins: azoxystrobin, coumethoxystrobin, coumoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyribencarb, trifloxystrobin, 2-[2-(2,5-dimethyl-phenoxymethyl)-phenyl]-3-methoxy-acrylic acid methyl ester and 2 (2-(3-(2,6-dichlorophenyl)-1-methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino-N methylacetamide; oxazolidinediones and imidazolinones: famoxadone, fenamidone;

  • F.I-2) Inhibitors of complex II (e.g. carboxamides): carboxanilides: benodanil, bixafen, boscalid, carboxin, fenfuram, fenhexamid, fluopyram, flutolanil, furametpyr, isopyrazam, isotianil, mepronil, oxycarboxin, penflufen, penthiopyrad, sedaxane, tecloftalam, thifluzamide, tiadinil, 2-amino-4 methyl-thiazole-5-carboxanilide, N-(3′,4′,5′ trifluorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N-(4′-trifluoromethylthiobiphenyl-2-yl)-3 difluoromethyl-1-methyl-1H pyrazole-4-carboxamide and N-(2-(1,3,3-trimethyl-butyl)-phenyl)-1,3-dimethyl-5 fluoro-1H-pyrazole-4 carboxamide;


    F.I-3) Inhibitors of Complex III at Qi Site: Cyazofamid, Amisulbrom;

  • F.I-4) Other respiration inhibitors (complex I, uncouplers) diflumetorim; tecnazen; ferimzone; ametoctradin; silthiofam; nitrophenyl derivates: binapacryl, dinobuton, dinocap, fluazinam, nitrthal-isopropyl, organometal compounds: fentin salts, such as fentin-acetate, fentin chloride or fentin hydroxide;


    F.II) Sterol Biosynthesis Inhibitors (SBI Fungicides)

  • F.II-1) C14 demethylase inhibitors (DMI fungicides, e.g. triazoles, imidazoles) triazoles: azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, paclobutrazole, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole; imidazoles: imazalil, pefurazoate, oxpoconazole, prochloraz, triflumizole; pyrimidines, pyridines and piperazines: fenarimol, nuarimol, pyrifenox, triforine;

  • F.II-2) Delta14-reductase inhitors (Amines, e.g. morpholines, piperidines) morpholines: aldimorph, dodemorph, dodemorph-acetate, fenpropimorph, tridemorph; piperidines: fenpropidin, piperalin; spiroketalamines: spiroxamine;

  • F.II-3) Inhibitors of 3-keto reductase: hydroxyanilides: fenhexamid;


    F.III) Nucleic Acid Synthesis Inhibitors

  • F.III-1) RNA, DNA synthesis phenylamides or acyl amino acid fungicides: benalaxyl, benalaxyl-M, kiralaxyl, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl; isoxazoles and iosothiazolones: hymexazole, octhilinone;

  • F.III-2) DNA topisomerase inhibitors: oxolinic acid;

  • F.III-3) Nucleotide metabolism (e.g. adenosin-deaminase) hydroxy(2-amino)-pyrimidines: bupirimate;


    F.IV) Inhibitors of Cell Division and or Cytoskeleton

  • F.IV-1) Tubulin inhibitors: benzimidazoles and thiophanates: benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate-methyl; triazolopyrimidines: 5-chloro-7 (4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5a]pyrimidine

  • F.IV-2) other cell division inhibitors benzamides and phenyl acetamides: diethofencarb, ethaboxam, pencycuron, fluopicolide, zoxamide;

  • F.IV-3) Actin inhibitors: benzophenones: metrafenone;


    F.V) Inhibitors of Amino Acid and Protein Synthesis

  • F.V-1) Mmethionine synthesis inhibitors (anilino-pyrimidines)

  • anilino-pyrimidines: cyprodinil, mepanipyrim, nitrapyrin, pyrimethanil;

  • F.V-2) Protein Synthesis Inhibitors (Anilino-Pyrimidines) antibiotics: blasticidin-S, kasugamycin, kasugamycin hydrochloride-hydrate, mildiomycin, streptomycin, oxytetracyclin, polyoxine, validamycin A;


    F.VI) Signal Transduction Inhibitors

  • F.VI-1) MAP/Histidine kinase inhibitors (e.g. anilino-pyrimidines) dicarboximides: fluoroimid, iprodione, procymidone, vinclozolin; phenylpyrroles: fenpiclonil, fludioxonil;

  • F.VI-2) G protein inhibitors: quinolines: quinoxyfen;


    F.VII) Lipid and Membrane Synthesis Inhibitors

  • F.VII-1) Phospholipid biosynthesis inhibitors organophosphorus compounds: edifenphos, iprobenfos, pyrazophos; dithiolanes: isoprothiolane;

  • F.VII-2) Lipid peroxidation aromatic hydrocarbons: dicloran, quintozene, tecnazene, tolclofos-methyl, biphenyl, chloroneb, etridiazole;

  • F.VII-3) Carboxyl acid amides (CAA fungicides) cinnamic or mandelic acid amides: dimethomorph, flumorph, mandiproamid, pyrimorph; valinamide carbamates: benthiavalicarb, iprovalicarb, pyribencarb, valifenalate and N-(1-(1-(4-cyano-phenyl)ethanesulfonyl)-but-2-yl) carbamic acid-(4-fluorophenyl)ester;

  • F.VII-4) Compounds affecting cell membrane permeability and fatty acides carbamates: propamocarb, propamocarb-hydrochlorid


    F.VIII) Inhibitors with Multi Site Action

  • F.VIII-1) Inorganic active substances: Bordeaux mixture, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur;

  • F.VIII-2) Thio- and dithiocarbamates: ferbam, mancozeb, maneb, metam, methasulphocarb, metiram, propineb, thiram, zineb, ziram;

  • F.VIII-3) Organochlorine compounds (e.g. phthalimides, sulfamides, chloronitriles): anilazine, chlorothalonil, captafol, captan, folpet, dichlofluanid, dichlorophen, flusulfamide, hexachlorobenzene, pentachlorphenole and its salts, phthalide, tolylfluanid, N-(4-chloro-2-nitro-phenyl)-N-ethyl-4-methyl-benzenesulfonamide;

  • F.VIII-4) Guanidines: guanidine, dodine, dodine free base, guazatine, guazatineacetate, iminoctadine, iminoctadine-triacetate, iminoctadine-tris(albesilate);

  • F.VIII-5) Ahtraquinones: dithianon;


    F.IX) Cell Wall Synthesis Inhibitors

  • F.IX-1) Inhibitors of glucan synthesis: validamycin, polyoxin B;

  • F.IX-2) Melanin synthesis inhibitors: pyroquilon, tricyclazole, carpropamide, dicyclomet, fenoxanil;


    F.X) Plant Defence Inducers

  • F.X-1) Salicylic acid pathway: acibenzolar-5-methyl;

  • F.X-2) Others: probenazole, isotianil, tiadinil, prohexadione-calcium; phosphonates: fosetyl, fosetyl-aluminum, phosphorous acid and its salts;


    F.XI) Unknown Mode of Action:

  • bronopol, chinomethionat, cyflufenamid, cymoxanil, dazomet, debacarb, diclomezine, difenzoquat, difenzoquat-methylsulfate, diphenylamin, flumetover, flusulfamide, flutianil, methasulfocarb, oxin-copper, proquinazid, tebufloquin, tecloftalam, triazoxide, 2-butoxy-6-iodo-3-propylchromen-4-one, N-(cyclopropylmethoxyimino-(6-difluoromethoxy-2,3-difluoro-phenyl)-methyl)-2-phenyl acetamide, N′-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N methyl formamidine, N′ (4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl formamidine, N′-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl formamidine, N′-(5-difluoromethyl-2 methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl formamidine, 2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazole-1-yl)-acetyl]-piperidin-4-yl}-thiazole-4-carboxylic acid methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)amide, 2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazole-1-yl)-acetyl]-piperidin-4-yl}-thiazole-4-carboxylic acid methyl-(R)-1,2,3,4-tetrahydro-naphthalen-1-yl-amide, methoxy-acetic acid 6-tert-butyl-8-fluoro-2,3-dimethyl-quinolin-4-yl ester and N-Methyl-2-{1-[(5-methyl-3-trifluoromethyl-1H-pyrazol-1-yl)-acetyl]-piperidin-4-yl}-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-4-thiazolecarboxamide, 3-[5-(4-chloro-phenyl)-2,3-dimethylisoxazolidin-3-yl]-pyridine (pyrisoxazole), 3-[5-(4-methyl-phenyl)-2,3-dimethylisoxazolidin-3-yl]-pyridine, 5-amino-2-isopropyl-3-oxo-4-ortho-tolyl-2,3-dihydropyrazole-1 carbothioic acid S-allyl ester, N-(6-methoxy-pyridin-3-yl)cyclopropanecarboxylic acid amide, 5-chloro-1 (4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1Hbenzoimidazole, 2-(4-chloro-phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxy-acetamide;


    F.XII) Growth Regulators:

  • abscisic acid, 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 and uniconazole;


    F.XIII) Biological Control Agents

  • antifungal biocontrol agents: Bacillus substilis strain with NRRL No. B-21661 (e.g. RHAPSODY®, SERENADE® MAX and SERENADE® ASO from AgraQuest, Inc., USA), Bacillus pumilus strain with NRRL No. B-30087 (e.g. SONATA® and BALLAD® Plus from AgraQuest, Inc., USA), Ulocladium oudemansii (e.g. the product BOTRYZEN from BotriZen Ltd., New Zealand), Chitosan (e.g. ARMOUR-ZEN from BotriZen Ltd., New Zealand).



The invertebrate pest, i.e. arthropodes and nematodes, the plant, soil or water in which the plant is growing can be contacted with the present compound(s) of formula I or composition(s) containing them by any application method known in the art. As such, “contacting” includes both direct contact (applying the compounds/compositions directly on the animal pest or plant—typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds/compositions to the locus of the animal pest or plant).


Moreover, invertebrate pests may be controlled by contacting the target pest, its food supply, habitat, breeding ground or its locus with a pesticidally effective amount of compounds of formula I. As such, the application may be carried out before or after the infection of the locus, growing crops, or harvested crops by the pest.


“Locus” means a habitat, breeding ground, cultivated plants, plant propagation material (such as seed), soil, area, material or environ-ment in which a pest or parasite is growing or may grow.


In general “pesticidally effective amount” means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The pesticidally effective amount can vary for the various compounds/compositions used in the invention. A pesticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired pesticidal effect and duration, weather, target species, locus, mode of application, and the like.


The compounds of formula I and their compositions can be used for protecting wooden materials such as trees, board fences, sleepers, etc. and buildings such as houses, outhouses, factories, but also construction materials, furniture, leathers, fibers, vinyl articles, electric wires and cables etc. from ants and/or termites, and for controlling ants and termites from doing harm to crops or human being (e.g. when the pests invade into houses and public facilities). The compounds of are applied not only to the surrounding soil surface or into the under-floor soil in order to protect wooden materials but it can also be applied to lumbered articles such as surfaces of the under-floor concrete, alcove posts, beams, plywood, furniture, etc., wooden articles such as particle boards, half boards, etc. and vinyl articles such as coated electric wires, vinyl sheets, heat insulating material such as styrene foams, etc. In case of application against ants doing harm to crops or human beings, the ant controller of the present invention is applied to the crops or the surrounding soil, or is directly applied to the nest of ants or the like.


The compounds of formula I can also be applied preventively to places at which occurrence of the pests is expected.


The compounds of formula I may be also used to protect growing plants from attack or infestation by pests by contacting the plant with a pesticidally effective amount of compounds of formula I. As such, “contacting” includes both direct contact (applying the compounds/compositions directly on the pest and/or plant—typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds/compositions to the locus of the pest and/or plant).


In the case of soil treatment or of application to the pests dwelling place or nest, the quantity of active ingredient ranges from 0.0001 to 500 g per 100 m2, preferably from 0.001 to 20 g per 100 m2.


Customary application rates in the protection of materials are, for example, from 0.01 g to 1000 g of active compound per m2 treated material, desirably from 0.1 g to 50 g per m2.


Insecticidal compositions for use in the impregnation of materials typically contain from 0.001 to 95% by weight, preferably from 0.1 to 45% by weight, and more preferably from 1 to 25% by weight of at least one repellent and/or insecticide.


For use in bait compositions, the typical content of active ingredient is from 0.001% by weight to 15% by weight, desirably from 0.001% by weight to 5% by weight of active compound.


For use in spray compositions, the content of active ingredient is from 0.001 to 80% by weight, preferably from 0.01 to 50% by weight and most preferably from 0.01 to 15% by weight.


For use in treating crop plants, the rate of application of the active ingredients of this invention may be in the range of 0.1 g to 4000 g per hectare, desirably from 25 g to 600 g per hectare, more desirably from 50 g to 500 g per hectare.


In the treatment of seed, the application rates of the active ingredients are generally from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, in particular from 1 g to 200 g per 100 kg of seed.


The present invention is now illustrated in further detail by the following examples.







I. PREPARATION EXAMPLES

Compounds were characterized e.g. by coupled High Performance Liquid Chromatography/mass spectrometry (HPLC/MS), by 1H-NMR and/or by their melting points.


Analytical HPLC column: RP-18 column Chromolith Speed ROD from Merck KgaA, Germany). Elution: acetonitrile+0.1% trifluoroacetic acid (TFA)/water+0.1% trifluoroacetic acid (TFA) in a ratio of from 5:95 to 95:5 in 5 minutes at 40° C.



1H-NMR, respectively 13C-NMR: The signals are characterized by chemical shift (ppm) vs. tetramethylsilane, respectively CDCl3 for 13C-NMR, by their multiplicity and by their integral (relative number of hydrogen atoms given). The following abbreviations are used to characterize the multiplicity of the signals: m=multiplett, q=quartett, t=triplett, d=doublet and s=singulett.


S. Syntheses
S.1 Synthesis of 4-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2-yl]-2-methyl-benzaldehyde-ethylsemicarbazone (Compound 1.1 of table C.1)
Step 1: Synthesis of 4-bromo-3-methyl-N-trimethylsilanylmethyl-benzamide

To a suspension of 4-bromo-3-methylbenzoic acid (25.00 g, 116.3 mmol) in CH2Cl2 (300 mL) was added N,N-dimethyl aminopyridine (2.13 g, 17.4 mmol), followed by N-ethyl-N-dimethylamine propylcarbodiimide hydrochloride (22.39 g) in small portions. After 30 min at room temperature, amonimethyl trimethylsilane (12.2 g, 8.62 mL, 118 mmol) was added while maintaining the temperature at 20° C. After stirring over night, water was added and the organic layer was separated. The aqueous layer was extracted twice with CH2Cl2 and the combined organic phases were dried and evaporated in vacuum. The residue was purified by flash chromatography on silica gel to give the title compound (32.75 g, 94%).


Characterization by 1H-NMR (400 MHz, CDCl3):


δ [delta]=0.15 (s, 9H), 2.45 (s, 3H), 2.97 (m, 2H), 6.17 (br. s, 1H), 7.39 (m, 1H), 7.59 (m, 1H), 7.63 (m, 1H) ppm.


Step 2: Synthesis of 4-bromo-3-methyl-N-trimethylsilanylmethyl-thiobenzamide

To a suspension of 4-bromo-3-methyl-N-trimethylsilanylmethyl-benzamide (32.75 g, 109.1 mmol) in toluene (250 mL) was added Lawesson's reagent (31.32 g, 77.44 mmol) at room temperature. The mixture was heated at reflux for 1 h and cooled to ambient temperature. After adsorption of the reaction mixture on silica gel, the solvents were distilled off in vacuum. The residue was purified by flash chromatography on silica gel to give the title compound (30.3 g, 88%).


Characterization by 1H-NMR (400 MHz, CDCl3):


δ [delta]=0.15 (s, 9H), 2.40 (s, 3H), 3.47 (m, 2H), 7.28 (m, 1H), 7.51 (m, 1H), 7.58 (m, 1H) ppm.


Step 3: Synthesis of 4-bromo-3-methyl-N-trimethylsilanylmethyl-thiobenzimidic acid methyl ester

To a solution of 4-bromo-3-methyl-N-trimethylsilanylmethyl-thiobenzamide (5.00 g, 15.8 mmol) in THF (30 mL) was added methyl iodide (1.97 mL, 4.49 g, 31.6 mmol) and Cs2CO3 (10.3 g, 31.6 mmol) at −5° C. After 1 h at this temperature, the mixture was allowed to reach room temperature and stirred over night. Water was added and the mixture was extracted three times with MTBE. The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuum. The residue was purified by filtration over a short plug of silica gel to give the title compound (4.4 g), which was used in the next step without further purification.


Step 4: Synthesis of 5-(4-bromo-3-methyl-phenyl)-3-(3,5-dichloro-phenyl)-3-trifluoromethyl-3,4-dihydro-2H-pyrrole

To a solution of 4-bromo-3-methyl-N-trimethylsilanylmethyl-thiobenzimidic acid methyl ester (4.40 g, 13.3 mmol) in dry THF (60 mL) was added 2-(3,5-dichlorophenyl)-1,1,1-trifluoro-2-propene (4.35 g, 16.25 mmol) at −7° C. A solution of tetrabutyl ammoniumfluoride (5.32 mL, 1 M in THF, 5.33 mmol) was added at this temperature and the mixture was allowed to warm to room temperature over night. All volatiles were removed in vacuum. The residue was purified by flash chromatography on silica gel to give the title compound (4.50 g, 75%).


Characterization by HPLC-MS: 4.643 min, M=451.95


Characterization by 1H-NMR (400 MHz, CDCl3):


δ [delta]=2.45 (s, 3H), 3.44 (d, 1H), 3.76 (d, 1H), 4.42 (d, 1H), 4.88 (d, 1H), 7.26 (s, 2H), 7.38 (m, 1H), 7.50 (m, 1H) 7.61 (d, 1H), 7.72 (s, 1H) ppm.


Step 5: Synthesis of 4-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2-yl]-2-methyl-benzaldehyde

A mixture of 5-(4-bromo-3-methyl-phenyl)-3-(3,5-dichloro-phenyl)-3-trifluoromethyl-3,4-dihydro-2H-pyrrole (2.00 g, 4.43 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) (162 mg, 0.229 mmol), triethylsilane (1.42 mL, 1.03 g, 8.87 mmol) and Na2CO3 (587 mg, 5.54 mmol) in DMF (30 mL) were purged with CO gas at 65° C. The mixture was stirred over night at 65° C. and then cooled to room temperature. The residue was purified by flash chromatography on silica gel to give the title compound (1.316 g, 74%).


Characterization by 1H-NMR (400 MHz, CDCl3):


δ [delta]=2.72 (s, 3H), 3.49 (d, 1H), 3.83 (d, 1H), 4.48 (d, 1H), 4.92 (d, 1H), 7.27 (s, 2H), 7.39 (s, 1H), 7.79 (s, 1H) 7.81 (d, 1H), 7.90 (m, 1H), 10.34 (s, 1H) ppm.


Step 6: Synthesis of 4-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2-yl]-2-methyl-benzaldehyde-ethylsemicarbazone

A mixture of 4-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2-yl]-2-methyl-benzaldehyde (208 mg, 0.520 mmol) and ethyl semicarbazide hydrochloride (109 mg 0.780 mmol) in ethanol (5 mL) and glacial acetic acid (0.1 mL) was heated at 70° C. for 4 h. After cooling, the mixture was concentrated in vacuum. The residue was purified by flash chromatography on silica gel to give the title compound (151 mg, 60%).


Characterization by HPLC-MS: 3.741 min, M=485.00


Characterization by 1H-NMR (400 MHz, DMSO-d6):


δ [delta]=1.09 (t, 3H), 2.43 (s, 3H), 3.19 (m, 2H), 3.70 (d, 1H), 3.88 (d, 1H), 4.40 (d, 1H), 4.82 (d, 1H), 7.07 (m, 1H), 7.58 (s, 2H), 7.71 (s, 1H), 7.75 (m, 2H), 8.09 (d, 1H), 8.14 (s, 1H), 10.36 (s, 1H) ppm.


S.2 Synthesis of 4-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2-yl]-2-methyl-benzaldehyde-ethylthiosemicarbazone (Compound 1.2 of table C.1)

A mixture of 4-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2-yl]-2-methyl-benzaldehyde (208 mg, 0.520 mmol) and ethyl thiosemicarbazide (93 mg 0.12 mmol) in ethanol (5 mL) and glacial acetic acid (0.1 mL) was heated at 70° C. for 4 h. After cooling, the resulting precipitate was filtered and dried to give the title compound (198 mg, 76%).


Characterization by HPLC-MS: 4.141 min, M=501.05


Characterization by 1H-NMR (400 MHz, DMSO-d6):


δ [delta]=1.14 (t, 3H), 2.43 (s, 3H), 3.60 (m, 2H), 3.70 (d, 1H), 3.89 (d, 1H), 4.42 (d, 1H), 4.82 (d, 1H), 7.59 (s, 1H), 7.62 (s, 1H), 7.78 (m, 2H), 8.18 (m, 1H), 8.42 (s, 1H), 8.60 (m, 1H), 11.42 (s, 1H) ppm.


S.3 Synthesis of 4-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2-yl]-2-chloro-benzaldehyde-ethylsemicarbazone (Compound 2.1 of table C.2)
Step 1: Synthesis of 4-bromo-3-chloro-N-trimethylsilanylmethyl-benzamide

To a suspension of 4-bromo-3-chlorobenzoic acid (25.00 g, 106.2 mmol) in CH2Cl2 (320 mL) was added N,N-dimethyl aminopyridine (1.95 g), followed by N-ethyl-N-dimethylamine propylcarbodiimide hydrochloride (22.39 g) in small portions. After 30 min at room temperature, aminomethyl trimethylsilane (11.2 g, 7.87 mL, 108 mmol) was added while maintaining the temperature at 20° C. After stirring over night, water was added and the organic layer was separated. The aqueous layer was extracted twice with CH2Cl2 and the combined organic phases were dried and evaporated in vacuum. The residue was purified by flash chromatography on silica gel to give the title compound (34.00 g, 100%).


Characterization by 1H-NMR (400 MHz, CDCl3):


δ [delta]=0.15 (s, 9H), 2.96 (m, 2H), 6.07 (br. s, 1H), 7.50 (m, 1H), 7.69 (m, 1H), 7.86 (m, 1H) ppm.


Step 2: Synthesis of 4-bromo-3-chloro-N-trimethylsilanylmethyl-thiobenzamide

To a suspension of 4-bromo-3-chloro-N-trimethylsilanylmethyl-benzamide (34.00 g, 106.0 mmol) in toluene (250 mL) was added Lawesson's reagent (30.45 g, 75.28 mmol) at room temperature. The mixture was heated at reflux for 1 h and cooled to ambient temperature. After adsorption of the reaction mixture on silica gel the solvents were distilled off in vacuum. The residue was purified by flash chromatography on silica gel to give the title compound (31.3 g, 88%).


Characterization by 1H-NMR (400 MHz, CDCl3):


δ [delta]=0.15 (s, 9H), 3.47 (m, 2H), 7.36 (m, 1H), 7.50-7.64 (m, 2H), 7.77 (d, 1H) ppm.


Step 3: Synthesis of 4-bromo-3-chloro-N-trimethylsilanylmethyl-thiobenzimidic acid methyl ester

To a solution of 4-bromo-3-chloro-N-trimethylsilanylmethyl-thiobenzamide (10.40 g, 30.88 mmol) in THF (200 mL) was added methyl iodide (5.77 mL, 13.15 g, 92.7 mmol) and Cs2CO3 (30.19 g, 92.7 mmol) at −5° C. After 1 h at this temperature, the mixture was heated at 40° C. and stirred over night. Water was added and the mixture was extracted three times with MTBE. The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuum. The residue was purified by filtration over a short plug of silica gel to give the title compound (8.25 g), which was used in the next step without further purification.


Step 4: Synthesis of 5-(4-bromo-3-chloro-phenyl)-3-(3,5-dichloro-phenyl)-3-trifluoromethyl-3,4-dihydro-2H-pyrrole

To a solution of 4-bromo-3-chloro-N-trimethylsilanylmethyl-thiobenzimidic acid methyl ester (9.60 g, 27.4 mmol) in dry THF (100 mL) was added 2-(3,5-dichlorophenyl)-1,1,1-trifluoro-2-propene (8.94 g, 33.4 mmol) at −7° C. A solution of tetrabutyl ammoniumfluoride (5.32 mL, 1 M in THF, 5.33 mmol) was added at this temperature and the mixture was allowed to warm to room temperature over night. All volatiles were removed in vacuum. The residue was purified by flash chromatography on silica gel to give the title compound (9.50 g, 74%).


Characterization by HPLC-MS: 4.944 min, M=471.90


Characterization by 1H-NMR (400 MHz, CDCl3):


δ [delta]=3.43 (d, 1H), 3.76 (d, 1H), 4.43 (d, 1H), 4.90 (d, 1H), 7.26 (s, 3H), 7.59 (m, 1H), 7.70 (m, 1H) 7.92 (s, 1H) ppm.


Step 5: Synthesis of 4-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2-yl]-2-chloro-benzoic acid methyl ester

A mixture of 5-(4-bromo-3-chloro-phenyl)-3-(3,5-dichloro-phenyl)-3-trifluoromethyl-3,4-dihydro-2H-pyrrole (10.60 g), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) (1.645 mg), sodium acetate (2.748 g) and methanol (100 mL) was placed in an autoclave and purged with CO gas. The pressure was adjusted to 5 bar and the mixture was heated at 80° C. for 16 h. After cooling the pressure was released and the solvents were distilled off in vacuum. The residue was purified by flash chromatography on silica gel to give the title compound (10.00 g, 99%).


Characterization by 1H-NMR (400 MHz, CDCl3):


δ [delta]=3.47 (d, 1H), 3.80 (d, 1H), 3.96 (s, 3H), 4.48 (d, 1H), 4.93 (d, 1H), 7.26 (s, 3H), 7.80 (m, 1H) 7.90-7.98 (m, 2H) ppm.


Step 6: Synthesis of 4-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2-yl]-2-chloro-benzaldehyde

To a solution of 4-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2-yl]-2-chloro-benzoic acid methyl ester (807 mg, 1.79 mmol) in CH2Cl2 (100 mL) was added a solution of DIBAL (1.97 mL, 1 M in CH2Cl2, 1.97 mmol) with a syringe pump at −75° C. The mixture was stirred for 25 min at this temperature, before methanol (1 mL) was added and warmed to room temperature. Saturared aqueous Na/K-tartrate solution was added and the mixture was extracted three times with CH2Cl2. The organic layers were combined, dried over Na2SO4 and concentrated in vacuum. The residue was purified by flash chromatography on silica gel to give the title compound (190 mg, 25%).


Characterization by 1H-NMR (400 MHz, CDCl3):


δ [delta]=3.48 (d, 1H), 3.80 (d, 1H), 4.49 (d, 1H), 4.95 (d, 1H), 7.27 (s, 3H), 7.85 (m, 1H) 7.95-8.06 (m, 2H), 10.51 (s, 1H) ppm.


Step 7: Synthesis of 4-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2-yl]-2-chloro-benzaldehyde-ethylsemicarbazone

A mixture of 4-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2-yl]-2-chloro-benzaldehyde (121 mg, 0.29 mmol) and ethyl semicarbazide hydrochloride (60 mg 0.43 mmol) in ethanol (5 mL) and glacial acetic acid (0.1 mL) was heated at 70° C. for 4 h. Then, water was added and cooled, upon which a precipitate formed. The latter was collected by filtration and dried in vacuum to obtain the title compound (137 mg, 93%).


Characterization by HPLC-MS: 4.159 min, M=505.05


Characterization by 1H-NMR (400 MHz, DMSO-d6):


δ [delta]=1.09 (t, 3H), 3.19 (m, 2H), 3.75 (d, 1H), 3.91 (d, 1H), 4.43 (d, 1H), 4.85 (d, 1H), 7.27 (m, 1H), 7.60 (s, 2H), 7.71 (s, 1H), 7.90 (d, 1H), 7.96 (s, 1H), 8.27 (s, 1H), 8.34 (s, 1H), 10.69 (s, 1H) ppm.


S.4 Synthesis of 1-[(E)-[4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-2,4-dihydropyrrol-5-yl]-2-methyl-phenyl]methyleneamino]-3-(2,2,2-trifluoroethyl)urea (Compound 1-3 of table C.1)
Step 1: Synthesis of 4-bromo-3-methyl-N-(trimethylsilylmethyl)benzamide

To a suspension of 4-bromo-3-methylbenzoic acid (25 g) and 4-(dimethylamino)pyridine (“DMAP”, 2.1 g) in CH2Cl2 (320 mL) was added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (“EDC”, 22.4 g) portionwise. Then, (aminomethyl)trimethylsilane (8.6 mL) was added, while cooling to keep the internal temperature below 20° C. The reaction was stirred at room temperature overnight. Water was added under vigorous stirring, and the layers were separated. The aqueous layer was extracted twice with CH2Cl2, and the combined organic phase dried (Na2SO4), and filtered over silica gel using CH2Cl2 and methyl tert-butyl ether (MTBE) to afford the title compound (32.8 g, 94%).


Characterization by HPLC-MS: 3.628 min, M=302.00.


Step 2: Synthesis of 4-bromo-3-methyl-N-(trimethylsilylmethyl)benzenecarbothioamide

To a suspension of 4-bromo-3-methyl-N-(trimethylsilylmethyl)benzamide (i.e. the product of Step 1, 32.8 g) in toluene (250 mL) was added 2,4-bis(4-methoxyphenyl)-2,4-dithioxo-1,3,2,4-dithiadiphosphetane (“Lawesson's reagent”, 31.3 g). The mixture was heated at reflux for 1 h, cooled to room temperature and concentrated. Purification by flash chromatography on silica gel afforded the title compound (30.3 g, 88%).


Characterization by HPLC-MS: 4.184 min, M=317.90.


Step 3: Synthesis of methyl (1Z)-4-bromo-3-methyl-N-(trimethylsilylmethyl)benzenecarboximidothioate

At −5° C., 4-bromo-3-methyl-N-(trimethylsilylmethyl)benzenecarbothioamide (i.e. the product of Step 2, 1.0 g) in THF (15 mL) was treated with methyliodide (0.30 mL). NaHCO3 (0.80 g) was added portionwise and the reaction was stirred at room temperature for 72 h. Then, MTBE and brine were added. The aqueous phase was extracted three times with MTBE and the combined organic layers washed with brine, dried (Na2SO4), filtered and concentrated. Purification by flash chromatography on silica gel afforded the title compound (0.735 g, 70%).


Characterization by HPLC-MS: 2.890 min, M=330.00.


Step 4: Synthesis of 5-(4-bromo-3-methyl-phenyl)-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-2,4-dihydropyrrole

To methyl (1Z)-4-bromo-3-methyl-N-(trimethylsilylmethyl)benzenecarboximidothioate (i.e. the product of Step 3, 4.4 g) in THF (100 mL) was added 1,3-dichloro-5-[1-(trifluoromethyl)vinyl]benzene (8.9 g). Between −7° C. and -5° C., a solution of tetrabutylammoniumfluoride (1 M in THF, 10.9 mL) was added. The reaction was allowed to warm to room temperature and was stirred for 72 h. The reaction was concentrated and the crude product purified by flash chromatography on silica gel and subsequently recrystallized from petrolether to afford the title compound (9.5 g, 74%).


Characterization by HPLC-MS: 4.944 min, M=471.90.


Step 5: Synthesis of 4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-2,4-dihydropyrrol-5-yl]-2-methyl-benzaldehyde

To a solution of 5-(4-bromo-3-methyl-phenyl)-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-2,4-dihydropyrrole (i.e. the product of Step 4, 2.0 g) in dimethylformamide (DMF) (50 mL) was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (“Pd(dppf)Cl2”, 0.16 g), Na2CO3 (0.59 g) and triethylsilane (1.4 mL). The mixture was purged twice with N2, then purged three times with CO and stirred under an atmosphere of CO overnight at 65° C. Then, the reaction was concentrated in vacuum and purified by flash chromatography on silica gel to afford the title compound (1.32 g, 74%).


Characterization by HPLC-MS: 4.322 min, M=400.00


Step 6: Synthesis of 1-[(E)-[4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-2,4-dihydropyrrol-5-yl]-2-methyl-phenyl]methyleneamino]-3-(2,2,2-trifluoroethyl)urea

A mixture of 4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-2,4-dihydropyrrol-5-yl]-2-methyl-benzaldehyde (i.e. the product of Step 5, 200 mg), 1-amino-3-(2,2,2-trifluoroethyl)urea (145 mg) and acetic acid (0.1 mL) in EtOH (5 mL) was heated at 70° C. for 4 h. Water was added, the reaction cooled to room temperature and the solid was collected by filtration. Recrystallization from diisopropylether yielded the title compound (198 mg, 73%).


Characterization by HPLC-MS: 3.967 min, M=539.05


The following examples were synthesized analogously.


C. COMPOUND EXAMPLES

The following examples were synthesized in analogy to the Synthesis examples.


C.1 Compound Examples 1

Compound examples 1-1 to 1-10 correspond to compounds of formula C.1:




embedded image



wherein R1, R2 and Y of each synthesized compound is defined in one row of table C.1 below.














TABLE C.1





Com-







pound



Rt



Ex.
R1
R2
Y
(min)
[M + H]







1-1
H
C(═O)NH—CH2CH3
NH
3.741
485.00


1-2
H
C(═S)NH—CH2CH3
NH
4.141
501.05


1-3
H
C(═O)NH—CH2CF3
NH
3.967
539.05


1-4
H
C(═O)NH—CH3
NH
3.573
471.00


1-5
H
C(═O)—NH-cyclopropyl
NH
3.772
497.00


1-6
H
C(═O)—NH—CH2-cyclopropyl
NH
3.948
511.10


1-7
H
C(═O)NH—CH2CH2CH3
NH
3.796
499.00


1-8
H
C(═O)NH—CH2CH2CF3
NH
3.993
553.00


1-9
H
C(═O)NH—CH2CHF2
NH
3.834
521.05


 1-10
H
C(═O)NH2
NH
3.324
457.00









C.2 Compound Examples 2

Compound example 2-1 to 2-10 corresponds to compound formula C.2:




embedded image



wherein R1, R2, and Y of each synthesized compound is defined in one row of table C.2 below.














TABLE C.2





Com-







pound



Rt


Ex.
R1
R2
Y
(min)
[M + H]







2-1
H
C(═O)NH—CH2CH3
NH
4.159
505.05


2-2
H
C(═S)NH—CH2CH3
NH
4.452
522.90


2-3
H
C(═O)NH—CH2CF3
NH
4.307
559.25


2-4
H
C(═O)NH—CH3
NH
4.011
491.45


2-5
H
C(═O)—NH-cyclopropyl
NH
4.176
516.95


2-6
H
C(═O)—NH—CH2-cyclopropyl
NH
4.336
531.05


2-7
H
C(═O)NH—CH2CH2CH3
NH
4.314
519.05


2-8
H
C(═O)NH—CH2CH2CF3
NH
4.336
572.90


2-9
H
C(═O)NH—CH2CHF2
NH
4.164
540.90


 2-10
H
C(═O)NH2
NH
3.837
476.90










II. Evaluation Of Pesticidal Activity:


The activity of the compounds of formula I of the present invention can be demonstrated and evaluated by the following biological test.


B.1 Cotton Aphid (Aphis Gossypii)


The active compounds were formulated in cyclohexanone as a 10,000 ppm solution supplied in tubes. The tubes were inserted into an automated electrostatic sprayer equipped with an atomizing nozzle and they served as stock solutions for which lower dilutions were made in 50% acetone:50% water (v/v). A nonionic surfactant (Kinetic) was included in the solution at a volume of 0.01% (v/v).


Cotton plants at the cotyledon stage were infested with aphids prior to treatment by placing a heavily infested leaf from the main aphid colony on top of each cotyledon. Aphids were allowed to transfer overnight to accomplish an infestation of 80-100 aphids per plant and the host leaf was removed. The infested plants were then sprayed by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in the sprayer fume hood, removed from the sprayer, and then maintained in a growth room under fluorescent lighting in a 24-hr photoperiod at 25° C. and 20-40% relative humidity. Aphid mortality on the treated plants, relative to mortality on untreated control plants, was determined after 5 days.


In this test, the compounds 1-4, 1-5, 2-1 and 2-5, respectively, at 300 ppm showed a mortality of at least 75% in comparison with untreated controls.


B.2 Cowpea Aphid (Aphis Craccivora)


Potted cowpea plants colonized with approximately 100-150 aphids of various stages were sprayed after the pest population had been recorded. Population reduction was assessed after 24, 72, and 120 hours.


In this test, the compounds 1-2, 1-3, 1-5, 1-8, 2-3 and 2-5, respectively, at 500 ppm showed a mortality of at least 75% in comparison with untreated controls.


B.3 Diamond Back Moth (Plutella Xylostella)


Leaves of Chinese cabbage were dipped in test solution and air-dried. Treated leaves were placed in petri dished lined with moist filter paper. Mortality was recorded 24, 72, and 120 hours after treatment.


In this test, the compounds 1-1, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 2-1, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8 and 2-9, respectively, at 500 ppm showed a mortality of at least 75% in comparison with untreated controls.


B.4 Green Peach Aphid (Myzus Persicae)


For evaluating control of green peach aphid (Myzus persicae) through systemic means the test unit consisted of 96-well-microtiter plates containing liquid artificial diet under an artificial membrane.


The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were pipetted into the aphid diet, using a custom built pipetter, at two replications.


After application, 5-8 adult aphids were placed on the artificial membrane inside the microtiter plate wells. The aphids were then allowed to suck on the treated aphid diet and incubated at about 23±1° C. and about 50±5% relative humidity for 3 days. Aphid mortality and fecundity was then visually assessed.


In this test, the compounds 1-1, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 2-1, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8 and 2-9, respectively, at 2500 ppm showed a mortality of at least 75% in comparison with untreated controls.


B.5 Mediterranean Fruitfly (Ceratitis Capitata)


For evaluating control of Mediterranean fruitfly (Ceratitis capitata) the test unit consisted of microtiter plates containing an insect diet and 50-80 C. capitata eggs.


The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were sprayed onto the insect diet at 5 μl, using a custom built micro atomizer, at two replications.


After application, microtiter plates were incubated at about 28±1° C. and about 80±5% relative humidity for 5 days. Egg and larval mortality was then visually assessed.


In this test, the compounds 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10, 2-1, 2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8, 2-9 and 2-10, respectively, at 2500 ppm, showed a mortality of at least 75% in comparison with untreated controls.


B.6 Orchid Thrips (Dichromothrips corbetti)



Dichromothrips corbettiadults used for bioassay were obtained from a colony maintained continuously under laboratory conditions. For testing purposes, the test compound was diluted to a concentration of 500 ppm (wt compound: vol diluent) in a 1:1 mixture of acetone:water (vol:vol), plus 0.01% vol/vol Kinetic® surfactant.



Thrips potency of each compound was evaluated by using a floral-immersion technique. Plastic petri dishes were used as test arenas. All petals of individual, intact or chid flowers were dipped into treatment solution and allowed to dry. Treated flowers were placed into individual petri dishes along with 10-15 adult thrips. The petri dishes were then covered with lids. All test arenas were held under continuous light and a temperature of about 28° C. for duration of the assay. After 4 days, the numbers of live thrips were counted on each flower, and along inner walls of each petri dish. The level of thrips mortality was extrapolated from pre-treatment thrips numbers.


In this test, the compounds 1-1, 1-3, 1-4, 1-5, 1-6, 1-8, 1-9, 2-1, 2-3, 2-4, 2-5, 2-7 and 2-8, respectively, at 500 ppm showed a mortality of at least 75% in comparison with untreated controls.


B.7 Rice Green Leafhopper (Nephotettix Virescens)


Rice seedlings were cleaned and washed 24 hours before spraying. The active compounds were formulated in 50:50 acetone:water (vol:vol), and 0.1% vol/vol surfactant (EL 620) was added. Potted rice seedlings were sprayed with 5 ml test solution, air dried, placed in cages and inoculated with 10 adults. Treated rice plants were kept at about 28-29° C. and relative humidity of about 50-60%. Percent mortality was recorded after 72 hours.


In this test, the compounds 1-4, 2-3, 2-4 and 2-5, respectively, at 500 ppm showed a mortality of at least 75% in comparison with untreated controls.


B.8 Silverleaf Whitefly (Bemisia Argentifolii)


The active compounds were formulated in cyclohexanone as a 10,000 ppm solution supplied in tubes. The tubes were inserted into an automated electrostatic sprayer equipped with an atomizing nozzle and they served as stock solutions for which lower dilutions were made in 50% acetone:50% water (v/v). A nonionic surfactant (Kinetic) was included in the solution at a volume of 0.01% (v/v).


Cotton plants at the cotyledon stage (one plant per pot) were sprayed by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in the sprayer fume hood and then removed from the sprayer. Each pot was placed into a plastic cup and about 10 to 12 whitefly adults (approximately 3-5 days old) were introduced. The insects were collected using an aspirator and a nontoxic Tygon® tubing connected to a barrier pipette tip. The tip, containing the collected insects, was then gently inserted into the soil containing the treated plant, allowing insects to crawl out of the tip to reach the foliage for feeding. Cups were covered with a reusable screened lid. Test plants were maintained in a growth room at about 25° C. and about 20-40% relative humidity for 3 days, avoiding direct exposure to fluorescent light (24 hour photoperiod) to prevent trapping of heat inside the cup. Mortality was assessed 3 days after treatment, compared to untreated control plants.


In this test, the compound 2-3, at 300 ppm showed a mortality of at least 75% in comparison with untreated controls.


B.9 Southern Armyworm (Spodoptera Eridania)


The active compounds were formulated in cyclohexanone as a 10,000 ppm solution supplied in tubes. The tubes were inserted into an automated electrostatic sprayer equipped with an atomizing nozzle and they served as stock solutions for which lower dilutions were made in 50% acetone:50% water (v/v). A nonionic surfactant (Kinetic®) was included in the solution at a volume of 0.01% (v/v).


Lima bean plants (variety Sieva) were grown 2 plants to a pot and selected for treatment at the 1st true leaf stage. Test solutions were sprayed onto the foliage by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in the sprayer fume hood and then removed from the sprayer. Each pot was placed into perforated plastic bags with a zip closure. About 10 to 11 armyworm larvae were placed into the bag and the bags zipped closed. Test plants were maintained in a growth room at about 25° C. and about 20-40% relative humidity for 4 days, avoiding direct exposure to fluorescent light (24 hour photoperiod) to prevent trapping of heat inside the bags. Mortality and reduced feeding was assessed 4 days after treatment, compared to untreated control plants.


In this test, the compounds 1-1, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 2-1, 2-2, 2-3, 2-4, 2-5, 2-6, 2-8 and 2-9, respectively, at 1 ppm showed a mortality of at least 75% in comparison with untreated controls.


B.10 Vetch Aphid (Megoura Viciae)


For evaluating control of vetch aphid (Megoura viciae) through contact or systemic means the test unit consisted of 24-well-microtiter plates containing broad bean leaf disks.


The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were sprayed onto the leaf disks at 2.5 μl, using a custom built micro atomizer, at two replications.


After application, the leaf disks were air-dried and 5-8 adult aphids placed on the leaf disks inside the microtiter plate wells. The aphids were then allowed to suck on the treated leaf disks and incubated at about 23±1° C. and about 50±5% relative humidity for 5 days. Aphid mortality and fecundity was then visually assessed.


In this test, the compounds 1-1, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 2-1, 2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8 and 2-9, respectively, at 2500 ppm, showed a mortality of at least 75% in comparison with untreated controls.


B.11 Tobacco Budworm (Heliothis Virescens) I


For evaluating control of tobacco budworm (Heliothis virescens) the test unit consisted of 96-well-microtiter plates containing an insect diet and 15-25 H. virescens eggs. The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were sprayed onto the insect diet at 10 μl, using a custom built micro atomizer, at two replications.


After application, microtiter plates were incubated at about 28±1° C. and about 80±5% relative humidity for 5 days. Egg and larval mortality was then visually assessed.


In this test, the compounds 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-8, 1-9, 1-10, 2-1, 2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8, 2-9 and 2-10, respectively, at 2500 ppm, showed a mortality of at least 75% in comparison with untreated controls.


B.12 Boll Weevil (Anthonomus Grandis)


For evaluating control of boll weevil (Anthonomus grandis) the test unit consisted of 24-well-microtiter plates containing an insect diet and 20-30 A. grandis eggs.


The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were sprayed onto the insect diet at 20 μl, using a custom built micro atomizer, at two replications. After application, microtiter plates were incubated at about 23±1° C. and about 50±5% relative humidity for 5 days. Egg and larval mortality was then visually assessed.


In this test, the compounds 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-8, 1-9, 1-10, 2-1, 2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8, 2-9 and 2-10, respectively, at 2500 ppm, showed a mortality of at least 75% in comparison with untreated controls.


B.13 Colorado Potato Beetle (Leptinotarsa Decemlineata)


The active compounds were formulated in cyclohexanone as a 10,000 ppm solution supplied in tubes. The tubes were inserted into an automated electrostatic sprayer equipped with an atomizing nozzle and they served as stock solutions for which lower dilutions were made in 50% acetone:50% water (v/v). A nonionic surfactant (Kinetic®) was included in the solution at a volume of 0.01% (v/v).


Eggplants were grown 2 plants to a pot and were selected for treatment at the 1st true leaf stage. Test solutions were sprayed onto the foliage by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in the sprayer fume hood and then removed from the sprayer. The treated foliage was then cut and removed from the pot and placed in a 5-inch Petri dish lined with moistened filter paper. Five beetle larvae were introduced into each Petri dish and the dish was covered by a Petri dish lid. Petri dishes were maintained in a growth room at 25° C. and 20-40% relative humidity for 4 days, avoiding direct exposure to fluorescent light (24 hour photoperiod) to prevent trapping of heat inside the dishes. Mortality and reduced feeding were assessed 4 days after treatment, compared to untreated control plants.


In this test, the compound 2-4, at 10 ppm showed a mortality of at least 75% in comparison with untreated controls.


B.14 Red Spider Mite (Tetranychus Kanzawai)


The active compound was dissolved at the desired concentration in a mixture of 1:1 (v/v) distilled water:acetone. A surfactant (Alkamuls® EL 620) was added at the rate of 0.1% (v/v).


Potted cowpea beans of 7-10 days of age were cleaned with tap water and sprayed with 5 ml of the test solution using air driven hand atomizer. The treated plants were allowed to air dry and afterwards inculated with 20 or more mites by clipping a cassaya leaf section with known mite population. Treated plants were placed inside a holding room at about 25-27° C. and about 50-60% relative humidity.


Mortality was determined by counting the live mites 72 HAT. Percent mortality was assessed after 72 h.


In this test, the compounds 1-1, 1-3, 1-5, 1-7, 1-8, 2-1, 2-4, 2-5 and 2-8, respectively, at 500 ppm showed a mortality of at least 75% in comparison with untreated controls.

Claims
  • 1. A compound of formula (I)
  • 2. The compound of claim 1, wherein B1 is CH.
  • 3. The compound of claim 1, wherein A1 is CH.
  • 4. The compound of claim 1, wherein X is selected from the group consisting of C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-haloalkoxy-C1-C4-alkyl, C3-C6-cycloalkyl and C3-C6-halocycloalkyl.
  • 5. The compound of claim 4, wherein X is selected from the group consisting of CF3, CHF2 and CF2Cl.
  • 6. The compound of claim 1, wherein R′ is selected from the group consisting of hydrogen; cyano; C1-C10-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; C1-C10-alkoxy; C1-C10-haloalkoxy; C3-C8-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; C2-C10-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; C2-C10-alkynyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; —C(═O)R6; —C(═O)OR7; —C(═O)N(R8)R9; —C(═S)R6; —C(═S)OR7; —C(═S)N(R8)R9; phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10.
  • 7. The compound of claim 6, wherein R1 is selected from the group consisting of hydrogen; cyano; C1-C10-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; C1-C10-alkoxy; C1-C10-haloalkoxy; C3-C8-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; C2-C10-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; C2-C10-alkynyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; —C(═O)R6; phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10.
  • 8. The compound of claim 7, wherein R1 is selected from the group consisting of hydrogen; cyano; C1-C6-alkyl; C1-C4-haloalkyl; C1-C4-alkoxy; C1-C4-haloalkoxy; and —C(═O)R6.
  • 9. The compound of claim 1, wherein R3 is selected from the group consisting of hydrogen; cyano; C1-C10-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; C3-C8-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; C2-C10-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; C2-C10-alkynyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; —N(R8)R9; —Si(R14)2R13; —OR7; —SR7; —S(O)mR7; —S(O)nN(R)R9; —C(═O)R6; —C(═O)OR7; —C(═O)N(R8)R9; —C(═S)R6; —C(═S)OR7; —C(═S)N(R8)R9; —C(═NR8)R6; phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10; or R2 and R3 together form a group ═CR11, R12; ═S(O)mR7; ═S(O)mN(R8)R9; ═NR8; or ═NOR7; or R2 and R3 together form a C2-C7 alkylene chain, thus forming, together with the nitrogen atom to which they are bound, a 3-, 4-, 5-, 6-, 7- or 8-membered ring, where the alkylene chain may be interrupted by 1 or 2 0, S and/or NR18 and/or 1 or 2 of the CH2 groups of the alkylene chain may be replaced by a group C═O, C═S and/or C═NR18; and/or the alkylene chain may be substituted by one or more radicals selected from the group consisting of halogen, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R′.
  • 10. The compounds according claim 9, wherein R3 is selected from the group consisting of hydrogen; C1-C10-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; C3-C8-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; C2-C10-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; C2-C10-alkynyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; —C(═O)R6; —C(═O)OR7; —C(═O)N(R8)R9; —C(═S)R6; —C(═S)OR7; —C(═S)N(R8)R9; —C(═NR8)R6; phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10.
  • 11. The compounds according claim 10, wherein R3 is selected from the group consisting of hydrogen; C1-C6-alkyl and C1-C4-haloalkyl.
  • 12. The compound of claim 1, wherein each R4 is independently selected from the group consisting of halogen; cyano; nitro; —SCN; SF5; C1-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; C3-C8-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; C2-C6-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; C2-C6-alkynyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; —Si(R14)2R13; —OR7; —OS(O)nR7; —SR7; —S(O)mR7; —S(O)nN(R8)R9; —N(R8)R9; —N(R8)C(═O)R6; C(═O)R6; —C(═O)OR7; —C(═NR8)H; —C(═NR8)R6; —C(═O)N(R8)R9; C(═S)N(R8)R9; phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals Ro1; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10; or two radicals R4 bound on adjacent carbon atoms may be together a group selected from the group consisting of —CH2CH2CH2CH2—, —CH═CH—CH═CH—, —N═CH—CH═CH—, —CH═N—CH═CH—, —N═CH—N═CH—, —OCH2CH2CH2—, —OCH═CHCH2—, —CH2OCH2CH2—, —OCH2CH2O—, —OCH2OCH2—, —CH2CH2CH2—, —CH═CHCH2—, —CH2CH2O—, —CH═CHO—, —CH2OCH2—, —CH2C(═O)O—, —C(═O)OCH2—, —O(CH2)O—, —SCH2CH2CH2—, —SCH═CHCH2—, —CH2SCH2CH2—, —SCH2CH2S—, —SCH2SCH2—, —CH2CH2S—, —CH═CHS—, —CH2SCH2—, —CH2C(═S)S—, —C(═S)SCH2—, —S(CH2)S—, —CH2CH2NR8—, —CH2CH═N—, —CH═CH—NR8—, —OCH═N—, and —SCH═N—, thus forming, together with the carbon atoms to which they are bound, a 5- or 6-membered ring, where the hydrogen atoms of the above groups may be replaced by one or more substituents selected from the group consisting of halogen, methyl, halomethyl, hydroxyl, methoxy and halomethoxy or one or more CH2 groups of the above groups may be replaced by a C═O group.
  • 13. The compound of claim 12, wherein each R4 is independently selected from the group consisting of halogen; cyano; nitro; —SCN; C1-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; C3-C8-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; —OR7; —OS(O)nR7; —SR7; —S(O)mR7; —S(O)nN(R8)R9; —N(R8)R9; C(═O)R6; —C(═O)OR7; —C(═NR8)R6; —C(═O)N(R8)R9; and —C(═S)N(R8)R9.
  • 14. The compounds according claim 13, wherein R4 is selected from the group consisting of halogen, cyano, C1-C4-alkyl and C1-C4-haloalkyl.
  • 15. The compound of claim 1, wherein each R5 is independently selected from the group consisting of halogen, cyano, nitro, —SCN, SF5, C1-C6-alkyl, C1-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6, C3-C8-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6, C2-C6-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6, C2-C6-alkynyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6, Si(R14)2R13, OR7, OS(O)nR7, S(O)mR7, NR8R9, N(R8)C(═O)R6, C(═O)R6, C(═O)OR7, C(═NR8)R6, C(═S)NR6, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10.
  • 16. The compounds according claim 15, wherein R5 is selected from the group consisting of halogen and C1-C4-haloalkyl.
  • 17. The compound of claim 1, wherein R2 is selected from the group consisting of hydrogen; C1-C10-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; C3-C8-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; C2-C10-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; C2-C10-alkynyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R6; —C(═O)R6; —C(═O)OR7; —C(═O)N(Rs)R9; —C(═S)R6; —C(═S)OR7, —C(═S)N(R8)R9; —C(═NR8)R6, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10.
  • 18. The compounds according claim 17, wherein R2 is selected from the group consisting of C1-C4-alkyl; C1-C4-haloalkyl; a methyl group substituted by a radical R6a; —C(═O)R6c; —C(═O)N(R8)R9; —C(═O)OR7; —C(═S)R6c; —C(═S)N(R8)R9; —C(═S)OR7; and —C(═NR8)R6d, whereR6a is selected from the group consisting of CN, phenyl which may carry 1, 2 or 3 substituents R10, —C(═O)R6b; —C(═O)N(R8)R9 and —C(═OO)OR7;R6b and R6c are independently selected from the group consisting of C1-C4-alkyl, C1-C4-haloalkyl, phenyl, benzyl and a 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2, as ring members, where the phenyl or heterocyclyl rings in the three last-mentioned radicals may carry 1, 2 or 3 substituents selected from the group consisting of halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;R6d is selected from N(R8)R9;R7 is selected from the group consisting of hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, phenyl, benzyl and a 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2, as ring members, where the phenyl or heterocyclyl rings in the three last-mentioned radicals may carry 1, 2 or 3 substituents selected from the group consisting of halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;each R8 is independently selected from the group consisting of hydrogen, cyano, C1-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, C2-C4-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, C3-C6-halocycloalkyl-C1-C4-alkyl, —S(O)mR20, —S(O)nN(R21)R22, phenyl, benzyl and a 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2, as ring members, where the phenyl or heterocyclyl rings in the three last-mentioned radicals may carry 1, 2 or 3 substituents selected from the group consisting of halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;each R9 is independently selected from the group consisting of hydrogen, cyano, C1-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, C2-C4-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, C3-C6-halocycloalkyl-C1-C4-alkyl, —S(O)mR20, —S(O)nN(R21)R22, phenyl, benzyl and a 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2, as ring members, where the phenyl or heterocyclyl rings in the three last-mentioned radicals may carry 1, 2 or 3 substituents selected from the group consisting of halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy; andR10 is selected from the group consisting of halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;where R19 is as defined in claim 1; or R8 and R9 together form a group ═CR11R12; orR8 and R9, together with the nitrogen atom to which they are bound, form a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring which may additionally containing 1 or 2 further heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10.
  • 19. The compounds according claim 18, wherein R2 is selected from the group consisting of —C(═O)N(R8)R9 and —C(═S)N(R8)R9; whereinR8 is selected from the group consisting of hydrogen and C1-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19;R9 is selected from the group consisting of hydrogen, C1-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl and C3-C6-halocycloalkyl-C1-C4-alkyl.
  • 20. The compounds according claim 19, where R8 is hydrogen; andR9 is selected from the group consisting of hydrogen, C1-C6-alkyl; C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl and C3-C6-halocycloalkyl-C1-C4-alkyl.
  • 21. The compound of claim 1, wherein Y is O, NR3 or a chemical bond.
  • 22. The compound of claim 1, wherein Y is NR3.
  • 23. The compound of claim 1, wherein p is 0, 1 or 2.
  • 24. The compound of claim 1, wherein q is 0, 1, 2 or 3.
  • 25. The compound of claim 1, of formula I-1
  • 26. The compound of claim 1, of formula I-A
  • 27. A compound of formula (II)
  • 28. The compounds of formula II according to claim 27, wherein Ra, Rb and Rc, independently of each other, are selected from C1-C4-alkyl; andRd is selected from the group consisting of hydrogen, C1-C4-alkyl and C1-C4-haloalkyl.
  • 29. An agricultural composition comprising a compound of claim 1 and at least one inert liquid and/or solid agriculturally acceptable carrier.
  • 30. A veterinary composition comprising a compound of claim 1 and/or at least one veterinarily acceptable salt thereof, and at least one inert liquid and/or solid veterinarily acceptable carrier.
  • 31. A method for controlling invertebrate pests which method comprises treating the pests, their food supply, their habitat or their breeding ground or a plant, plant propagation material, soil, area, material or environment in which the pests are growing or may grow, or the materials, plants, plant propagation material, soils, surfaces or spaces to be protected from invertebrate pest attack or infestation with a pesticidally effective amount of a compound of claim 1.
  • 32. The method as claimed in claim 31, wherein plants are protected from attack or infestation by invertebrate pests.
  • 33. The method as claimed in claim 31, for protecting plant propagation material and/or the plants which grow therefrom from attack or infestation by invertebrate pests, which method comprises treating the plant propagation material with a pesticidally effective amount of a compound of claim 1.
  • 34. Plant propagation material treated with a composition comprising a compound of claim 1.
  • 35. A method for treating or protecting an animal from infestation or infection by invertebrate pests which comprises bringing the animal in contact with a pesticidally effective amount of a compound of claim 1.
Parent Case Info

This application is a National Stage application of International Application No. PCT/EP2011/067088 filed Sep. 30, 2011, which claims the benefit of U.S. Provisional Application No. 61/388,636, filed Oct. 1, 2010, and U.S. Provisional Application No. 61/429,216, filed Jan. 3, 2011, the entire contents of which are hereby incorporated herein by reference.

PCT Information
Filing Document Filing Date Country Kind 371c Date
PCT/EP2011/067088 9/30/2011 WO 00 3/27/2013
Publishing Document Publishing Date Country Kind
WO2012/042007 4/5/2012 WO A
US Referenced Citations (1)
Number Name Date Kind
20110269804 Cassayre et al. Nov 2011 A1
Foreign Referenced Citations (8)
Number Date Country
WO 2008122375 Oct 2008 WO
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Non-Patent Literature Citations (2)
Entry
International Search Report dated Nov. 9, 2011, prepared in International Application No. PCT/EP2011/067088.
International Preliminary Report on Patentability dated Apr. 2, 2013, prepared in International Application No. PCT/EP2011/067088.
Related Publications (1)
Number Date Country
20130190378 A1 Jul 2013 US
Provisional Applications (2)
Number Date Country
61388636 Oct 2010 US
61429216 Jan 2011 US