TREA

BENZAMIDE COMPOUNDS AND THEIR USE AS HERBICIDES

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Information

  • Patent Application
  • 20200331866
  • Publication Number
    20200331866
  • Date Filed
    January 07, 2019
    5 years ago
  • Date Published
    October 22, 2020
    3 years ago
Information
Abstract
The present invention relates to benzamide compounds of formula (I), the N-oxides and the salts thereof (I), where the variables are as defined in the claims and the description. The invention also relates to compositions comprising such compounds and to the use of such compounds for controlling unwanted vegetation.
Description

The present invention relates to benzamide compounds, the N-oxides and the salts thereof and to compositions comprising the same. The invention also relates to the use of the benzamide compounds, the N-oxides or the salts thereof and to the use of the compositions comprising such compounds for controlling unwanted vegetation. Furthermore, the invention relates to methods of applying such compounds.


For the purposes of controlling unwanted vegetation, especially in crops, there is an ongoing need for new herbicides which have high activities and selectivities, preferably together with a substantial lack of toxicity for humans and animals.


WO 2012/028579 describes N-(tetrazol-4-yl)- and N-(triazol-3-yl)arylcarboxylic acid amide compounds which carry 3 substituents in the 2-, 3- and 4-positions of the aryl ring, and their use as herbicides.


WO 2013/017559 describes N-(tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxylic acid amides which carry 3 substituents in the 2-, 3- and 4-positions of the aryl ring, and their use as herbicides.


WO 2015/052153 describes N-(tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxylic acid amides which carry at least 2 substituents in the 2- and 6-positions of the aryl ring and a further substituent on the amide nitrogen, and their use as herbicides.


WO 2017/102275 describes N-(tetrazol-5-yl)- and N-(triazol-5-yl)benzamides which carry a urea group in 3-position and two further substituents in the 2- and 6-positions of the aryl ring, and their use as herbicides.


The compounds of the prior art often suffer from insufficient herbicidal activity in particular at low application rates and/or unsatisfactory selectivity resulting in a low compatibility with crop plants.


Accordingly, it is an object of the present invention to provide further benzamide compounds having a strong herbicidal activity, in particular even at low application rates, a sufficiently low toxicity for humans and animals and/or a high compatibility with crop plants. The benzamide compounds should also show a broad activity spectrum against a large number of different unwanted plants.


These and further objectives are achieved by the compounds of formula I defined below, their N-oxides and their agriculturally suitable salts.


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




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wherein

  • Q is selected from the group consisting of radicals of the formulae Q1, Q2, Q3 and Q4;




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where # in formulae Q1, Q2, Q3 and Q4 indicates the point of attachment to the nitrogen atom;

  • R1 is selected from the group consisting of cyano, halogen, nitro, C1-C8-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, C1-C8-haloalkyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-haloalkoxy-C1-C4-alkyl, C1-C8-alkoxy, C1-C4-alkoxy-C1-C4-alkoxy-Z1—, C1-C6-haloalkoxy, R1b—S(O)k—Z1—;
  • R2a is selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkylamino, di-C1-C6-alkylamino, C3-C10-cycloalkyl and C3-C10-cycloalkyl-C1-C4-alkyl, where the alkyl, alkoxy, alkenyl, alkynyl and cycloalkyl parts of the eight aforementioned radicals are unsubstituted, partially or completely halogenated, or substituted by 1 or 2 radicals R2f and where the cycloalkyl parts may also be fused to a benzene ring which is unsubstituted or substituted by 1, 2, 3 or 4 radicals R21 which are identical or different,
  • R2a may also be selected from the group consisting of phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1, 2, 3 or 4 heteroatoms as ring members which are selected from the group consisting of O, N and S, where phenyl and heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4 groups R21 which are identical or different;
  • R2b is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, where the alkyl, alkenyl, alkynyl and cycloalkyl parts of the five aforementioned radicals are unsubstituted, partially or completely halogenated, or substituted by 1 or 2 radicals R2f;
  • R2b may also be selected from the group consisting of phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1, 2, 3 or 4 heteroatoms as ring members which are selected from the group consisting of O, N and S, where phenyl and heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4 groups R21 which are identical or different; or
  • R2a and R2b, together with the nitrogen atom to which they are bound, may form a 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated heterocyclic radical which may contain as a ring member a further heteroatom selected from the group consisting of O, S and N and where the heterocyclic radical is unsubstituted or carries 1, 2, 3 or 4 groups R2d or carries 1 group R2e and 0, 1, 2 or 3 groups R2d;
  • R2c is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkylamino, di-C1-C6-alkylamino, C3-C10-cycloalkyl and C3-C10-cycloalkyl-C1-C4-alkyl, where the alkyl, alkenyl, alkynyl and cycloalkyl parts of the seven aforementioned radicals are unsubstituted, partially or completely halogenated, or substituted by 1 or 2 radicals R2f and where the cycloalkyl parts may also be fused to a benzene ring which is unsubstituted or substituted by 1, 2, 3 or 4 radicals R21 which are identical or different,
    • R2c may also be selected from the group consisting of phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1, 2, 3 or 4 heteroatoms as ring members which are selected from the group consisting of O, N and S, where phenyl and heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4 groups R21 which are identical or different;
  • R2d are identical or different and selected from the group consisting of halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy, or two groups R2d which are obound to adjacent carbon atoms may form together a fused benzene ring which is unsubstituted or substituted by 1, 2, 3 or 4 groups R21 which are identical or different;
  • R2e is selected from the group consisting of ═O, OH, R4b—S(O)k—Z4—, R4c—C(O)—Z4—, R4dO—C(O)—Z4—, R4eR4fN—C(O)—Z4—, R4gR4hN—Z4— and R4eR4fNS(O)2—Z4—;
  • R2f is selected from the group consisting of OH, CN, NH2, SH, SCN, nitro, tri(C1-C4-alkyl)silyl, C1-C4-alkoxy, C1-C4-haloalkoxy, R3eR3fN—, R3c—C(O)—, HO—C(O)—R3dO—C(O)—, R3dS—C(O)—, R3eR3fN—C(O)—, R3eR3fN—NR3h—C(O)—, R3c—C(S)—, R3dO—C(S)—, R3dS—C(S)—, R3eR3fN—C(S), R3c—S(O)n—, R3c—S(O)2—O—, R3dO—S(O)2—, R3eR3fNS(O)2—, R3c—C(O)—NR3g—, R3dO—C(O)—NR3g—, R3eR3fN—C(O)—NR3g—, R3eR3fN—NR3h—C(O)—NR3g—, R3dO—S(O)2—NR3g—, R3eR3fNS(O)2—NR3g—, R3c—C(O)—NR3g—C(O)—, R3dO—C(O)—NR3g—C(O)—, R3eR3fN—C(O)—NR3g—C(O)—, R3dO—S(O)2—NR3g—C(O)—, R3eR3fNS(O)2—NR3g—C(O)—, R3c—C(O)—NR3g—S(O)2—, R3dO—C(O)—NR3g—S(O)2—, R3eR3fN—C(O)—NR3g—S(O)2—, (OH)2P(O)—, (C1-C4-alkoxy)2P(O)—, R3dO—N═CH—, phenyl-X and heterocyclyl-X, where heterocyclyl in the last two mentioned radicals is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1, 2, 3 or 4 heteroatoms as ring members which are selected from the group consisting of O, N and S, where phenyl and heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4 groups R11 which are identical or different;
  • R3 is selected from the group consisting of hydrogen, cyano, thiocyanato, halogen, nitro, hydroxy-Z3—, C1-C6-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, C3-C10-cycloalkyl-Z3—, C3-C6-cycloalkenyl-Z3—, C3-C10-cycloalkoxy-Z3—, C3-C10-cycloalkyl-C1-C2-alkoxy, where the cyclic groups of the four aforementioned radicals are unsubstituted or partially or completely halogenated; C1-C4-cyanoalkyl, C1-C8-haloalkyl, C2-C8-haloalkenyl, C3-C8-haloalkynyl, C1-C8-alkoxy-Z3—, C1-C8-haloalkoxy-Z3—, C1-C4-alkoxy-C1-C4-alkoxy-Z3—, C1-C4-haloalkoxy-C1-C4-alkoxy-Z3—, C2-C8-alkenyloxy-Z3—, C2-C8-alkynyloxy-Z3—, C2-C8-haloalkenyloxy-Z3—, C3-C8-haloalkynyloxy-Z3—, R3b—S(O)k—Z3—, R3—C(O)—Z3—, R3dO—C(O)—Z3—, R3dO—N═CH—Z3—, R3eR3fN—C(O)—Z3—, R3gR3hN—Z3—, R22C(O)O—Z3—, R25O C(O)O—Z3—, (R22)2NC(O)O—Z3—, R25S(O)2O—Z3—, R22O S(O)2—Z3—, (R22)2NS(O)2—Z3—, R25O C(O)N(R22)—Z3—, (R22)2NC(O)N(R22)—Z3—, (R22)2NS(O)2N(R22)—Z3—, (OH)2P(O)—Z3—, (C1-C4-alkoxy)2P(O)—Z3—, phenyl-Z3a—, and heterocyclyl-Z3a—, where heterocyclyl is a 3-, 4-, 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle which contains 1, 2, 3 or 4 heteroatoms as ring members which are selected from the group consisting of O, N and S, where the cyclic groups in phenyl-Z3a— and heterocyclyl-Z3a— are unsubstituted or substituted by 1, 2, 3 or 4 groups R21 which are identical or different;
  • R4 is selected from the group consisting of hydrogen, halogen, cyano-Z1, C1-C8-alkyl, nitro, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated; C2-C8-alkenyl, C2-C8-alkynyl, C1-C8-haloalkyl, C1-C3-alkylamino, C1-C3-dialkylamino, C1-C3-alkylamino-S(O)k, C1-C3-alkylcarbonyl, C1-C8-alkoxy, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkoxy-Z1—, C1-C4-alkylthio-C1-C4-alkylthio-Z1—, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy, C1-C4-haloalkoxy-C1-C4-alkyl, C1-C4-haloalkoxy-C1-C4-alkoxy-Z1—, R1b—S(O)k—Z1—, phenoxy-Z1- and heterocyclyloxy-Z1—, where heterocyclyloxy is an oxygen-bound 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle which contains 1, 2, 3 or 4 heteroatoms as ring members which are selected from the group consisting of O, N and S, where the cyclic groups in phenoxy and heterocyclyloxy are unsubstituted or substituted by 1, 2, 3 or 4 groups R11 which are identical or different;
  • R5 is selected from the group consisting of hydrogen, halogen, cyano-Z1—, nitro, C1-C8-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated; C2-C8-alkenyl, C2-C8-alkynyl, C1-C8-haloalkyl, C1-C3-alkylamino, C1-C3-dialkylamino, C1-C3-alkylamino-S(O)k, C1-C3-alkylcarbonyl, C1-C8-alkoxy, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkoxy-Z1—, C1-C4-alkylthio-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkylthio-Z1—, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy, C1-C4-haloalkoxy-C1-C4-alkyl, C1-C4-haloalkoxy-C1-C4-alkoxy-Z1—, R1b—S(O)k—Z1—, phenoxy-Z1— and heterocyclyloxy-Z1—, where heterocyclyloxy is a 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle which is bound via an oxygen atom and which contains 1, 2, 3 or 4 heteroatoms as ring members which are selected from the group consisting of O, N and S, where the cyclic groups in phenoxy and heterocyclyloxy are unsubstituted or substituted by 1, 2, 3 or 4 groups R11 which are identical or different;
  • R6a, R6b, R6c, R6d, independently of each other, are selected from the group consisting of C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, where the C3-C7-cycloalkyl groups of the two aforementioned radicals are unsubstituted or partially or completely halogenated; C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C2-C6-haloalkenyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-haloalkoxy-C1-C4-alkyl, Rb—S(O)n—C1-C3-alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1, 2, 3 or 4 groups which are identical or different and selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;
  • R7 is selected from the group consisting of hydrogen, CN, NH2, C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, where the C3-C7-cycloalkyl groups of the two aforementioned radicals are unsubstituted or partially or completely halogenated; C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C2-C6-haloalkenyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-haloalkoxy-C1-C4-alkyl, C1-C4-cyanoalkyl, R3b—S( )k—Z3b—, R3c—C(O)—Z3b—, R3d—C(O)Z3b, R3dO—N═CH—Z3b—, R3eR3fN—C(O)—Z3b—, R3gR3hN—Z3b, R22C(O)O—Z3b, R25OC(O)O—Z3b, (R22)2NC(O)O—Z3b, R25S(O)2O—Z3b, R22O S(O)2—Z3b—, (R22)2NS(O)2—Z3b—, R25O C(O)N(R22)—Z3b, (R22)2NC(O)N(R22)—Z3b—(R22)2NS(O)2N(R22)—Z3b—, (OH)2P(O)—Z3b—, (C1-C4-alkoxy)2P(O)—Z3b—, phenyl-Z3a—, and heterocyclyl-Z3a—, where heterocyclyl is a 3-, 4-, 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle which contains 1, 2, 3 or 4 heteroatoms as ring members which are selected from the group consisting of O, N and S, where the cyclic groups in phenyl-Z3a— and heterocyclyl-Z3a— are unsubstituted or substituted by 1, 2, 3 or 4 groups R21 which are identical or different;
  • R11, R21, independently of each other, are selected from the group consisting of cyano, O H, halogen, nitro, C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-halocycloalkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C6-alkoxy, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl, C1-C4-haloalkoxy-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkoxy, C3-C7-cycloalkoxy and C1-C6-haloalkoxy, or two radicals R11 or R21, respectively which are bound to the same carbon atom, may form together a group ═O or two radicals R11 or R21, respectively which are bound to adjacent carbon atoms, may form together a group selected from C3-C5-alkylene, O—C2-C4-alkylene and O—(C1-C3-alkylene)-O—;
  • Z1, Z3, Z4, independently of each other, are selected from the group consisting of a covalent bond and C1-C4-alkanediyl which is unsubstituted or is partly or completely fluorinated;
  • Z2 is a covalent bond or a bivalent radical selected from C1-C4-alkanediyl and C1-C4-alkanediyl-O—C1-C4-alkanediyl,
    • where in the two last-mentioned radicals the C1-C4-alkanediyl groups are linear and where C1-C4-alkanediyl is unsubstituted or is partly or completely fluorinated or substituted by 1, 2, 3 or 4 groups Rz;
  • Z3a is selected from the group consisting of a covalent bond, C1-C4-alkanediyl, O—C1-C4-alkanediyl, C1-C4-alkanediyl-O and C1-C4-alkanediyl-O—C1-C4-alkanediyl;
  • Z3b is selected from the group consisting of C1-C4-alkanediyl, C1-C4-alkanediyl-O and C1-C4-alkanediyl-O—C1-C4-alkanediyl;
  • Rz are identical or different and selected from the group consisting of C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated; C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C1-C4-alkyl-C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkyl-S(O)n—C1-C4-alkyl, C1-C4-alkylamino-C1-C4-alkyl, C1-C4-dialkylamino-C1-C4-alkyl, C1-C6-cyanoalkyl, phenyl, benzyl, heterocyclyl and heterocyclylmethyl, where heterocyclyl in the last two mentioned radicals is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1, 2, 3 or 4 heteroatoms as ring members which are selected from the group consisting of O, N and S, where phenyl, benzyl, heterocyclyl and heterocyclylmethyl are unsubstituted or substituted by 1, 2, 3 or 4 groups which are identical or different and selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;
  • Rb, R1b, R3b, R4b, independently of each other, are selected from the group consisting of C1-C6-alkyl, C3-C7-cycloalkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1, 2, 3 or 4 heteroatoms as ring members which are selected from the group consisting of O, N and S, where phenyl and heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4 groups which are identical or different and selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;
  • R3c, R4c, independently of each other, are selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated; C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C1-C4-alkyl-C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkyl-S(O)n—C1-C4-alkyl, C1-C4-alkylamino-C1-C4-alkyl, C1-C4-dialkylamino-C1-C4-alkyl, C1-C6-cyanoalkyl, phenyl, benzyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1, 2, 3 or 4 heteroatoms as ring members which are selected from the group consisting of O, N and S, where phenyl, benzyl and heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4 groups which are identical or different and selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;
  • R3d, R4d, independently of each other, are selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated; C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C1-C4-alkyl-C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkyl-S(O)n—C1-C4-alkyl, C1-C4-alkylamino-C1-C4-alkyl, C1-C4-dialkylamino-C1-C4-alkyl, C1-C6-cyanoalkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1, 2, 3 or 4 groups which are identical or different and selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;
  • R3e, R3f, R4e, R4f, independently of each other, are selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated; C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4-alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1, 2, 3 or 4 groups which are identical or different and selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy; or
  • R3e and R3f or R4e and R4f, together with the nitrogen atom to which they are bound, may form a 4-, 5-, 6- or 7-membered, saturated or unsaturated heterocyclic radical which may contain as a ring member a further heteroatom selected from the group consisting of O, S and N and which is unsubstituted or carries 1, 2, 3 or 4 groups which are identical or different and selected from the group consisting of ═O, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;
  • R3g, R4g, independently of each other, are selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated; C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylsulfonyl, C1-C4-alkylcarbonyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1, 2, 3 or 4 groups which are identical or different and selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;
  • R3h, R4h, independently of each other, are selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated; C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylsulfonyl, C1-C4-alkylcarbonyl, a radical C(O)Rk, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1, 2, 3 or 4 groups which are identical or different and selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy; or
  • R3g and R3h or R4g and R4h, together with the nitrogen atom to which they are bound, may form a 4-, 5-, 6- or 7-membered, saturated or partially unsaturated heterocyclic radical which may contain as a ring member a further heteroatom selected from the group consisting of O, S and N and which is unsubstituted or carries 1, 2, 3 or 4 groups which are identical or different and selected from the group consisting of ═O, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;
  • R22 is selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkyl, C3-C6-cycloalkyl-C1-C6-alkoxy-C1-C6-alkyl, phenyl-Z1, phenyl-O—C1-C6-alkyl, phenyl-N(R23)—C1-C6-alkyl, phenyl-S(O)n—C1-C6-alkyl, heterocyclyl-Z1, heterocyclyl-N(R23)—C1-C6-alkyl, heterocyclyl-O—C1-C6-alkyl, and heterocyclyl-S(O)n—C1-C6-alkyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1, 2, 3 or 4 heteroatoms as ring members which are selected from the group consisting of O, N and S, where phenyl and heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4 groups which are identical or different and selected from the group consisting of cyano, halogen, nitro, thiocyanato, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C(O)OR23, C(O)N(R23)2, OR23, N(R23)2, S(O)nR24, S(O)2OR23, S(O)2N(R23)2, and R23O—C1-C6-alkyl, and where heterocyclyl bears 0, 1 or 2 oxo groups;
  • R23 is selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, and phenyl;
  • R24 is selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, and phenyl;
  • R25 is selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkyl, C3-C6-cycloalkyl-C1-C6-alkoxy-C1-C6-alkyl, phenyl-Z1, phenyl-O—C1-C6-alkyl, phenyl-N(R23)—C1-C6-alkyl, phenyl-S(O)n—C1-C6-alkyl, heterocyclyl-Z1, heterocyclyl-N(R23)—C1-C6-alkyl, heterocyclyl-O—C1-C6-alkyl, and heterocyclyl-S(O)n—C1-C6-alkyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1, 2, 3 or 4 heteroatoms as ring members which are selected from the group consisting of O, N and S, where phenyl and heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4 groups which are identical or different and selected from the group consisting of cyano, halogen, nitro, thiocyanato, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C(O)OR23, C(O)N(R23)2, OR23, N(R23)2, S(O)nR24, S(O)2OR23, S(O)2N(R23)2, and R23O—C1-C6-alkyl, and where heterocyclyl bears 0, 1 or 2 oxo groups;
  • X is a covalent bond, O, S(O)n or NR, where R is hydrogen or C1-C4-alkyl;
  • k is 0, 1 or 2;
  • n is 0, 1 or 2;
  • p is 0, 1 or 2; and
  • Rk has the meanings of R3c.


The present invention also relates to the N-oxides of the compounds of formula I, to the salts, in particular to the agriculturally suitable salts, of the compounds of formula I and to the salts of said N-oxides.


The compounds of the present invention, i.e. the compounds of formula I, their N-oxides and their agriculturally suitable salts, are particularly useful for controlling unwanted vegetation. Therefore, the invention also relates to the use of a compound of formula I of an N-oxide thereof or an agriculturally suitable salt thereof or of a composition comprising at least one compound of formula I, an N-oxide thereof or an agriculturally suitable salt thereof for combating or controlling unwanted vegetation.


The invention also relates to a composition comprising at least one compound of formula I, an N-oxide or a salt thereof, and at least one auxiliary. In particular, the invention relates to an agricultural composition comprising at least one compound of formula I or an agriculturally suitable salt thereof, and at least one auxiliary customary for crop protection formulations.


The present invention also relates to a method for combating or controlling unwanted vegetation, which method comprises allowing a herbicidally effective amount of at least one compound of formula I or a salt thereof to act on unwanted plants, their seed and/or their habitat.


Depending on the kind of substitutents, the compounds of formula I may have one or more centers of chirality, in which case they may be present as mixtures of enantiomers or diastereomers but also in the form of the pure enantiomers or pure diastereomers. The invention provides both the pure enantiomers or pure diastereomers of the compounds of formula I, and their mixtures and the use according to the invention of the pure enantiomers or pure diastereomers of the compound of formula I or its mixtures. Suitable compounds of formula I also include all possible geometrical stereoisomers (cis/trans isomers) and mixtures thereof. Cis/trans isomers may be present with respect to an alkene, carbon-nitrogen double-bond, nitrogen-sulfur double bond or amide group. The term “stereoisomer(s)” 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).


The present invention moreover relates to compounds as defined herein, wherein one or more of the atoms depicted in formula I have been replaced by its stable, preferably non-radioactive isotope (e.g., hydrogen by deuterium, 12C by 13C, 14N by 15N, 16O by 18O) and in particular wherein at least one hydrogen atom has been replaced by a deuterium atom. Of course, the compounds according to the invention contain more of the respective isotope than this naturally occurs and thus is anyway present in the compounds of formula I.


The compounds of the present invention may be amorphous or may exist in one ore more different crystalline states (polymorphs) which may have different macroscopic properties such as stability or show different biological properties such as activities. The present invention includes both amorphous and crystalline compounds of formula I, their enantiomers or diastereomers, mixtures of different crystalline states of the respective compound of formula I, its enantiomers or diastereomers, as well as amorphous or crystalline salts thereof.


Salts of the compounds of the present invention are preferably agriculturally suitable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid if the compound of the present invention has a basic functionality or by reacting the compound with a suitable base if the compound of the present invention has an acidic functionality.


Useful agriculturally suitable 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 herbicidal 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, tetrame-thylammonium, 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, hydrogensul-fate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate, car-bonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C1-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting compounds of the present invention with an acid of the corresponding anion, preferably with hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.


The term “N-oxides” relates to the derivatives of the compounds of formula I which bear at least one oxygen atom at a nitrogen atom. For example, the term “N-oxide” may relate to a derivative of a compound of formula I, wherein one of the imino nitrogens in the radicals Q1, Q2, Q3 or Q4 bears an oxygen atom. In other words, the N-oxides of compounds I are compounds in which a nitrogen atom, e.g. a ring nitrogen atom in the group Q or a nitrogen atom of an amino group, is present in oxidized form, i.e. as a group N+—O−. The N-oxides are generally prepared by oxidation of the compound of formula I, e.g. with hydrogen peroxide or peroxy acids like meta-chloroperoxybenzoic acid (mCPBA), peroxyacetic acid or Caro's acid (peroxymonosulfuric acid).


The term “undesired vegetation” (“weeds”) is understood to include any vegetation growing in non-crop-areas or at a crop plant site or locus of seeded and otherwise desired crop, where the vegetation is any plant species, including their germinant seeds, emerging seedlings and established vegetation, other than the seeded or desired crop (if any). Weeds, in the broadest sense, are plants considered undesirable in a particular location.


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 “partially or completely halogenated” will be taken to mean that 1 or more, e.g. 1, 2, 3, 4 or 5 or all of the hydrogen atoms of a given radical have been replaced by a halogen atom, in particular by fluorine or chlorine. A partially or completely halogenated radical is termed below also “halo-radical”. For example, partially or completely halogenated alkyl is also termed haloalkyl.


The term “alkyl” as used herein (and in the alkyl moieties of other groups comprising an alkyl group, e.g. alkoxy, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulfonyl and alkoxyalkyl) denotes in each case a straight-chain or branched alkyl group having usually from 1 to 10 carbon atoms (=C1-C10-alkyl) or 1 to 8 carbon atoms (=C1-C8-alkyl), frequently from 1 to 6 carbon atoms (=C1-C6-alkyl), in particular 1 to 4 carbon atoms (=C1-C4-alkyl) and especially from 1 to 3 carbon atoms (=C1-C3-alkyl) or 1 or 2 carbon atoms (=C1-C2-alkyl). C1-C2-Alkyl is methyl or ethyl. C1-C3-Alkyl is methyl, ethyl, n-propyl or iso-propyl. Examples of C1-C4-alkyl are methyl, ethyl, n-propyl, iso-propyl, n-butyl, 2-butyl (=sec-butyl), isobutyl and tert-butyl. Examples for C1-C6-alkyl are, apart those mentioned for C1-C4-alkyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl. Examples for C1-C8-alkyl are, apart those mentioned for C1-C6-alkyl, n-heptyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 1-ethylpentyl, 2-ethylpentyl, 3-ethylpentyl, n-octyl, 1-methylheptyl, 2-methylheptyl, 1-ethylhexyl, 2-ethylhexyl, 1,2-dimethylhexyl, 1-propylpentyl and 2-propylpentyl. Examples for C1-C10-alkyl are, apart those mentioned for C1-C5-alkyl, nonyl, decyl, 2-propylheptyl and 3-propylheptyl.


The term “haloalkyl” as used herein (and in the haloalkyl moieties of other groups comprising a haloalkyl group, e.g. haloalkoxy, haloalkylthio, haloalkylcarbonyl, haloalkylsulfonyl and haloalkylsulfinyl), which is also expressed as “alkyl which is partially or fully halogenated”, denotes in each case a straight-chain or branched alkyl group having usually from 1 to 8 carbon atoms (=C1-C8-haloalkyl), frequently from 1 to 6 carbon atoms (=C1-C6-haloalkyl), more frequently 1 to 4 carbon atoms (=C1-C4-haloalkyl), as defined above, wherein the hydrogen atoms of this group are partially or totally replaced with halogen atoms. “Fluorinated alkyl”, as used herein (and in the fluorinated alkyl moieties of other groups comprising a fluorinated alkyl group, e.g. fluorinated alkoxy), denotes in each case a straight-chain or branched alkyl group having usually from 1 to 8 carbon atoms (=fluorinated C1-C8-alkyl), frequently from 1 to 6 carbon atoms (=fluorinated C1-C6-alkyl), more frequently 1 to 4 carbon atoms (=fluorinated C1-C4-alkyl), in particular 1 or 2 carbon atoms (=fluorinated C1-C2-alkyl), as defined above, wherein the hydrogen atoms of this group are partially or totally replaced with fluorine atoms. Preferred haloalkyl moieties are selected from C1-C4-haloalkyl, more preferably from C1-C2-haloalkyl, more preferably from halomethyl, in particular from fluorinated C1-C2-alkyl. Halomethyl is methyl in which 1, 2 or 3 of the hydrogen atoms are replaced by halogen atoms. Examples are bromomethyl, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl and the like. Examples for fluorinated C1-C2-alkyl are fluoromethyl, difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, and the like. Examples for C1-C2-haloalkyl are, apart those mentioned for fluorinated C1-C2-alkyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 2-chloroethyl, 2,2-dichloroethyl, 2,2,2-trichloroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 1-bromoethyl, and the like. Examples for C1-C4-haloalkyl are, apart those mentioned for C1-C2-haloalkyl, 1-fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, heptafluoropropyl, 1,1,1-trifluoroprop-2-yl, 3-chloropropyl, 4-chlorobutyl and the like.


The term “cyanoalkyl” as used herein refers to straight-chain or branched alkyl groups having 1 to 4 (“C1-C4-cyanoalkyl”) or 1 to 6 (“C1-C6-cyanoalkyl) carbon atoms (as mentioned above), where 1 or 2, preferably 1, of the hydrogen atoms in these groups are replaced by a cyano (CN) group. Examples are cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 1-cyanopropyl, 2-cyanopropyl, 3-cyanopropyl, 1-cyanobutyl, 2-cyanobutyl, 3-cyanobutyl, 4-cyanobutyl and the like.


The term “cycloalkyl” as used herein (and in the cycloalkyl moieties of other groups comprising a cycloalkyl group, e.g. cycloalkoxy and cycloalkylalkyl) denotes in each case a mono- or bicyclic, saturated cycloaliphatic radical having usually from 3 to 10 carbon atoms (=C3-C10-cycloalkyl), preferably 3 to 7 carbon atoms (=C3-C7-cycloalkyl) or in particular 3 to 6 carbon atoms (=C3-C6-cycloalkyl). Examples of monocyclic saturated cycloaliphatic radicals having 3 to 6 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Examples of monocyclic saturated cycloaliphatic radicals having 3 to 7 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl. Examples of monocyclic radicals having 3 to 10 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooc-tyl, cyclononyl and cyclodecyl. C5-C6-Cycloalkyl is cyclopentyl or cyclohexyl. Examples of bicyclic radicals having 6 to 10 carbon atoms comprise bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[3.1.1]heptyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1]octyl. Preferably, the term cycloalkyl denotes a monocyclic saturated hydrocarbon radical. When cycloalkyl is fused to a benzene ring, the cycloalkyl ring is monocyclic, of course resulting together with the fused benzene ring in a bicyclic fused ring system. Cycloalkyl fused to a benzene ring is preferably C5-C6-cycloalkyl fused to a benzene ring. Examples for C5-C6-cycloalkyl fused to a benzene ring are indanyl and tetralinyl.


The term “halocycloalkyl” as used herein (and in the halocycloalkyl moieties of other groups comprising an halocycloalkyl group, e.g. halocycloalkylmethyl) denotes in each case a mono- or bicyclic cycloaliphatic radical having usually from 3 to 10 carbon atoms, preferably 3 to 7 carbon atoms or in particular 3 to 6 carbon atoms, wherein at least one, e.g. 1, 2, 3, 4 or 5 of the hydrogen atoms are replaced by halogen, in particular by fluorine or chlorine. Examples are 1- and 2-fluorocyclopropyl, 1,2-, 2,2- and 2,3-difluorocyclopropyl, 1,2,2-trifluorocyclopropyl, 2,2,3,3-tetrafluorocyclpropyl, 1- and 2-chlorocyclopropyl, 1,2-, 2,2- and 2,3-dichlorocyclopropyl, 1,2,2-trichlorocyclopropyl, 2,2,3,3-tetrachlorocyclpropyl, 1-,2- and 3-fluorocyclopentyl, 1,2-, 2,2-, 2,3-, 3,3-, 3,4-, 2,5-difluorocyclopentyl, 1-,2- and 3-chlorocyclopentyl, 1,2-, 2,2-, 2,3-, 3,3-, 3,4-, 2,5-dichlorocyclopentyl and the like.


The term “cycloalkyl-alkyl” used herein denotes a cycloalkyl group, as defined above, which is bound to the remainder of the molecule via an alkylene group. The term “C3-C7-cycloalkyl-C1-C4-alkyl” refers to a C3-C7-cycloalkyl group as defined above which is bound to the remainder of the molecule via a C1-C4-alkyl group, as defined above. The term “C3-C10-cycloalkyl-C1-C4-alkyl” refers to a C3-C10-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 cyclo-propylmethyl, cyclopropylethyl, cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl, cyclobutylpropyl, cyclopentylmethyl, cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl, cyclohexylpropyl, cycloheptylmethyl, cycloheptylethyl, cycloheptylpropyl and the like. The term “C3-C6-cycloalkyl-C1-C6-alkyl” refers to a C3-C6-cycloalkyl group as defined above which is bound to the remainder of the molecule via a C1-C6-alkyl group, as defined above. Examples are cyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl, cyclobutylpropyl, cyclopentylmethyl, cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl, cyclohexylpropyl and the like. The term “C3-C6-cycloalkyl-methyl” refers to a C3-C6-cycloalkyl group as defined above which is bound to the remainder of the molecule via a CH2 group. Examples are cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl and cyclohexylmethyl.


The term “cycloalkenyl” used herein denotes a monocyclic partially unsaturated, non-aromatic hydrocarbon radical. Examples for C3-C6-cycloalkenyl are cycloprop-1-en-1-yl, cyclo-prop-1-en-3-yl, cyclobut-1-en-1-yl, cyclobut-1-en-3-yl, cyclopent-1-en-1-yl, cyclopent-1-en-3-yl, cyclopent-1-en-4-yl, cyclopenta-1,3-dien-1-yl, cyclopenta-1,3-dien-2-yl, cyclopenta-1,3-dien-5-yl, cyclohex-1-en-1-yl, cyclohex-1-en-3-yl, cyclohex-1-en-4-yl, cyclohexa-1,3-dien-1-yl, cyclohexa-1,3-dien-2-yl, cyclohexa-1,3-dien-5-yl, cyclohexa-1,4-dien-1-yl and cyclohexa-1,4-dien-3-yl.


The term “alkenyl” as used herein denotes in each case a monounsaturated straight-chain or branched hydrocarbon radical having usually 2 to 8 (=C2-C8-alkenyl), preferably 2 to 6 carbon atoms (=C2-C6-alkenyl), in particular 2 to 4 carbon atoms (=C2-C4-alkenyl), 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-C8-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 and the positional isomers thereof.


C1-C4-alkyl-C2-C6-alkenyl corresponds to C3-C10-alkenyl. Examples are those mentioned above except for ethenyl.


The term “haloalkenyl” as used herein, which may also be expressed as “alkenyl which is substituted by halogen”, and the haloalkenyl moieties in haloalkenyloxy and the like refers to unsaturated straight-chain or branched hydrocarbon radicals having 2 to 8 (=C2-C8-haloalkenyl) or 2 to 6 (=C2-C6-haloalkenyl) or 2 to 4 (=C2-C4-haloalkenyl) carbon atoms and a double bond in any position, 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 chlo-rovinyl, chloroallyl and the like.


The term “alkynyl” as used herein denotes unsaturated straight-chain or branched hydrocarbon radicals having usually 2 to 8 (=C2-C8-alkynyl), frequently 2 to 6 (=C2-C6-alkynyl), preferably 2 to 4 carbon atoms (=C2-C4-alkynyl) and a triple bond 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 “haloalkynyl” as used herein, which is also expressed as “alkynyl which is substituted by halogen”, refers to unsaturated straight-chain or branched hydrocarbon radicals having usually 3 to 8 carbon atoms (=C3-C8-haloalkynyl), frequently 3 to 6 (=C3-C6-haloalkynyl), preferabyl 3 to 4 carbon atoms (=C3-C4-haloalkynyl), and a triple 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.


The term “alkoxy” as used herein denotes in each case a straight-chain or branched alkyl group usually having from 1 to 8 carbon atoms (=C1-C8-alkoxy), frequently from 1 to 6 carbon atoms (=C1-C6-alkoxy), preferably 1 to 4 carbon atoms (=C1-C4-alkoxy), in particular 1 or 2 carbon atoms (=C1-C2-alkoxy), which is bound to the remainder of the molecule 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 (isobu-toxy) or 1,1-dimethylethoxy (tert-butoxy). 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.


The term “haloalkoxy” as used herein denotes in each case a straight-chain or branched alkoxy group, as defined above, having from 1 to 8 carbon atoms (=C1-C8-haloalkoxy), frequently from 1 to 6 carbon atoms (=C1-C6-haloalkoxy), preferably 1 to 4 carbon atoms (=C1-C4-haloalkoxy), more preferably 1 to 3 carbon atoms (=C1-C3-haloalkoxy), in particular 1 or 2 carbon atoms (=C1-C2-haloalkoxy), wherein the hydrogen atoms of this group are partially or totally replaced with halogen atoms, in particular fluorine atoms (in this case, the radical is also termed fluorinated alkoxy). 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, unde-cafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluo-rohexoxy.


The term “alkenyloxy” denotes an alkenyl group, as defined above, attached via an oxygen atom to the remainder of the molecule. C2-C6-Alkenyloxy is a C2-C6-alkenyl group, as defined above, attached via an oxygen atom to the remainder of the molecule. C2-C8-Alkenyloxy is a C2-C8-alkenyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.


The term “haloalkenyloxy” denotes a haloalkenyl group, as defined above, attached via an oxygen atom to the remainder of the molecule. C2-C6-Haloalkenyloxy is a C2-C6-haloalkenyl group, as defined above, attached via an oxygen atom to the remainder of the molecule. C2-C8-Haloalkenyloxy is a C2-C8-haloalkenyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.


The term “alkynyloxy” denotes an alkynyl group, as defined above, attached via an oxygen atom to the remainder of the molecule. C2-C6-Alkynyloxy is a C2-C6-alkynyl group, as defined above, attached via an oxygen atom to the remainder of the molecule. C2-C8-Alkynyloxy is a C2-C8-alkynyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.


The term “haloalkynyloxy” denotes a haloalkynyl group, as defined above, attached via an oxygen atom to the remainder of the molecule. C2-C6-Haloalkynyloxy is a C2-C6-haloalkynyl group, as defined above, attached via an oxygen atom to the remainder of the molecule. C2-C8-Haloalkynyloxy is a C2-C8-haloalkynyl group, as defined above, attached via an oxygen atom to the remainder of the molecule. C3-C8-Haloalkynyloxy is a C3-C8-haloalkynyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.


The term “alkoxy-alkyl” as used herein denotes in each case alkyl usually comprising 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, wherein 1 carbon atom carries an alkoxy radical usually comprising 1 to 8, frequently 1 to 6, in particular 1 to 4, carbon atoms as defined above. The term “C1-C4-alkoxy-C1-C4-alkyl” relates to a C1-C4-alkyl group, as defined above, in which one hydrogen atom is replaced by a C1-C4-alkoxy group, as defined above. The term “C1-C6-alkoxy-C1-C6-alkyl” relates to a C1-C6-alkyl group, as defined above, in which one hydrogen atom is replaced by a C1-C6-alkoxy group, as defined above. Examples are CH2OCH3, CH2—OC2H5, n-propoxymethyl, CH2—OCH(CH3)2, n-butoxymethyl, (1-methylpropoxy)-methyl, (2-methylpropoxy)methyl, CH2—OC(CH3)3, 2-(methoxy)ethyl, 2-(ethoxy)ethyl, 2-(n-propoxy)-ethyl, 2-(1-methylethoxy)-ethyl, 2-(n-butoxy)ethyl, 2-(1-methylpropoxy)-ethyl, 2-(2-methylpropoxy)-ethyl, 2-(1,1-dimethylethoxy)-ethyl, 2-(methoxy)-propyl, 2-(ethoxy)-propyl, 2-(n-propoxy)-propyl, 2-(1-methylethoxy)-propyl, 2-(n-butoxy)-propyl, 2-(1-methylpropoxy)-propyl, 2-(2-methylpropoxy)-propyl, 2-(1,1-dimethylethoxy)-propyl, 3-(methoxy)-propyl, 3-(ethoxy)-propyl, 3-(n-propoxy)-propyl, 3-(1-methylethoxy)-propyl, 3-(n-butoxy)-propyl, 3-(1-methylpropoxy)-propyl, 3-(2-methylpropoxy)-propyl, 3-(1,1-dimethylethoxy)-propyl, 2-(methoxy)-butyl, 2-(ethoxy)-butyl, 2-(n-propoxy)-butyl, 2-(1-methylethoxy)-butyl, 2-(n-butoxy)-butyl, 2-(1-methylpropoxy)-butyl, 2-(2-methyl-propoxy)-butyl, 2-(1,1-dimethylethoxy)-butyl, 3-(methoxy)-butyl, 3-(ethoxy)-butyl, 3-(n-propoxy)-butyl, 3-(1-methylethoxy)-butyl, 3-(n-butoxy)-butyl, 3-(1-methylpropoxy)-butyl, 3-(2-methylpropoxy)-butyl, 3-(1,1-dimethylethoxy)-butyl, 4-(methoxy)-butyl, 4-(ethoxy)-butyl, 4-(n-propoxy)-butyl, 4-(1-methylethoxy)-butyl, 4-(n-butoxy)-butyl, 4-(1-methylpropoxy)-butyl, 4-(2-methylpropoxy)-butyl, 4-(1,1-dimethylethoxy)-butyl and the like.


The term “haloalkoxy-alkyl” as used herein denotes in each case alkyl as defined above, usually comprising 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, wherein 1 carbon atom carries an haloalkoxy radical as defined above, usually comprising 1 to 8, frequently 1 to 6, in particular 1 to 4, carbon atoms as defined above. Examples are fluoromethoxymethyl, difluoro-methoxymethyl, trifluoromethoxymethyl, 1-fluoroethoxymethyl, 2-fluoroethoxymethyl, 1,1-difluoroethoxymethyl, 1,2-difluoroethoxymethyl, 2,2-difluoroethoxymethyl, 1,1,2-trifluoroethoxymethyl, 1,2,2-trifluoroethoxymethyl, 2,2,2-trifluoroethoxymethyl, pentafluoroethox-ymethyl, 1-fluoroethoxy-1-ethyl, 2-fluoroethoxy-1-ethyl, 1,1-difluoroethoxy-1-ethyl, 1,2-difluoroethoxy-1-ethyl, 2,2-difluoroethoxy-1-ethyl, 1,1,2-trifluoroethoxy-1-ethyl, 1,2,2-trifluoroethoxy-1-ethyl, 2,2,2-trifluoroethoxy-1-ethyl, pentafluoroethoxy-1-ethyl, 1-fluoroethoxy-2-ethyl, 2-fluoroethoxy-2-ethyl, 1,1-difluoroethoxy-2-ethyl, 1,2-difluoroethoxy-2-ethyl, 2,2-difluoroethoxy-2-ethyl, 1,1,2-trifluoroethoxy-2-ethyl, 1,2,2-trifluoroethoxy-2-ethyl, 2,2,2-trifluoroethoxy-2-ethyl, pentafluoroethoxy-2-ethyl, and the like.


The term “alkoxy-alkoxy” as used herein, refers to an alkoxy group, as defined above, where one hydrogen atom is replaced by another alkoxy group, as defined above. The term “C1-C4-alkoxy-C1-C4-alkoxy” as used herein, refers to an alkoxy group having 1 to 4 carbon atoms, as defined above, where one hydrogen atom is replaced by a C1-C4-alkoxy group, as defined above. Examples are methoxymethoxy, ethoxymethoxy, propoxymethoxy, isopropoxymethoxy, n-butoxymethoxy, sec-butoxymethoxy, isobutoxymethoxy, tert-butoxymethoxy, 1-methoxyethoxy, 1-ethoxyethoxy, 1-propoxyethoxy, 1-isopropoxyethoxy, 1-n-butoxyethoxy, 1-sec-butoxyethoxy, 1-isobutoxyethoxy, 1-tert-butoxyethoxy, 2-methoxyethoxy, 2-ethoxyethoxy, 2-propoxyethoxy, 2-isopropoxyethoxy, 2-n-butoxyethoxy, 2-sec-butoxyethoxy, 2-isobutoxyethoxy, 2-tert-butoxyethoxy, 1-methoxypropoxy, 1-ethoxypropoxy, 1-propoxypropoxy, 1-isopropoxypropoxy, 1-n-butoxypropoxy, 1-sec-butoxypropoxy, 1-isobutoxypropoxy, 1-tert-butoxypropoxy, 2-methoxypropoxy, 2-ethoxypropoxy, 2-propoxypropoxy, 2-isopropoxypropoxy, 2-n-butoxypropoxy, 2-sec-butoxypropoxy, 2-isobutoxypropoxy, 2-tert-butoxypropoxy, 3-methoxypropoxy, 3-ethoxypropoxy, 3-propoxypropoxy, 3-isopropoxypropoxy, 3-n-butoxypropoxy, 3-sec-butoxypropoxy, 3-isobutoxypropoxy, 3-tert-butoxypropoxy and the like.


The term “haloalkoxy-alkoxy” denotes an alkoxy group, wherein one of the hydrogen atoms is replaced by an alkoxy group and wherein at least one, e.g. 1, 2, 3, 4 or all of the remaining hydrogen atoms (either in one or in both alkoxy moieties) are replaced by halogen atoms. C1-C4-Haloalkoxy-C1-C4-alkoxy is a C1-C4-alkoxy group, wherein one of the hydrogen atoms is replaced by a C1-C4-alkoxy group and wherein at least one, e.g. 1, 2, 3, 4 or all of the remaining hydrogen atoms (either in one or in both alkoxy moieties) are replaced by halogen atoms. Examples are difluoromethoxymethoxy (CHF2OCH2), trifluoromethoxymethoxy, 1-difluoromethoxyethoxy, 1-trifluoromethoxyethoxy, 2-difluoromethoxyethoxy, 2-trifluoromethoxyethoxy, difluoro-methoxy-methoxy (CH3OCF2), 1,1-difluoro-2-methoxyethoxy, 2,2-difluoro-2-methoxyethoxy and the like.


“Cycloalkoxy” denotes a cycloalkyl group, as defined above, bound to the remainder of the molecule via an oxygen atom. Examples of C3-C7-cycloalkoxy comprise cyclopropoxy, cyclobutoxy, cyclopentoxy, cyclohexoxy and cycloheptoxy. Examples of C3-C10-cycloalkoxy comprise cyclopropoxy, cyclobutoxy, cyclopentoxy, cyclohexoxy, cycloheptoxy, cyclooctoxy, cyclononoxy and cyclodecoxy.


The term “cycloalkyl-alkoxy” as used herein, refers to an alkoxy group, as defined above, where one hydrogen atom is replaced by a cycloalkyl group, as defined above. The term “C3-C10-cycloalkyl-C1-C2-alkoxy” as used herein, refers to an alkoxy group having 1 or 2 carbon atoms, as defined above, where one hydrogen atom is replaced by a C3-C10-cycloalkyl group, as defined above. Examples are cyclpropylmethoxy, cyclopropylethoxy, cyclobutylmethoxy, cyclo-butylethoxy, cyclopentylmethoxy, cyclopentylethoxy, cyclohexylmethoxy, cyclohexylethoxy, cycloheptylmethoxy, cycloheptylethoxy, cyclooctylmethoxy, cyclooctylethoxy, cyclononylmethoxy, cyclononylethoxy, cyclodecylmethoxy and cyclodecylethoxy.


The term “cycloalkyl-alkoxy-alkyl” as used herein, refers to an alkyl group, as defined above, wherein one hydrogen atom is replaced by an alkoxy group, as defined above, where in turn in the alkoxy group one hydrogen atom is replaced by a cycloalkyl group, as defined above. The term “C3-C6-cycloalkyl-C1-C6-alkoxy-C1-C6-alkyl” as used herein, refers to an alkyl group having 1 to 6 carbon atoms, as defined above, where one hydrogen atom is replaced by a C1-C6-alkoxy group, as defined above, where in this alkoxy group, in turn, one hydrogen atom is replaced by a C3-C6-cycloalkyl group, as defined above.


The term “alkylthio” (also alkylsulfanyl, “alkyl-S” or “alkyl-S(O)k” (wherein k is 0) as used herein denotes in each case a straight-chain or branched saturated alkyl group as defined above, usually comprising 1 to 8 carbon atoms (=C1-C8-alkylthio), frequently comprising 1 to 6 carbon atoms (=C1-C6-alkylthio), preferably 1 to 4 carbon atoms (=C1-C4-alkylthio), which is attached via a sulfur atom at any position in the alkyl group. C1-C2-Alkylthio is methylthio or ethylthio. C1-C4-Alkylthio is additionally, for example, n-propylthio, 1-methylethylthio (iso-propylthio), 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.


The term “haloalkylthio” as used herein refers to an alkylthio group as defined above wherein the hydrogen atoms are partially or completely substituted by fluorine, chlorine, bromine and/or iodine. C1-C2-Haloalkylthio is, for example, SCH2F, SCHF2, SCF3, SCH2Cl, SCHCl2, SCCl3, 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 terms “alkylsulfinyl” and “alkyl-S(O)k” (wherein k is 1) are equivalent and, as used herein, denote an alkyl group, as defined above, attached via a sulfinyl [S(O)] group. For example, the term “C1-C2-alkylsulfinyl” refers to a C1-C2-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term “C1-C4-alkylsulfinyl” refers to a C1-C4-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term “C1-C6-alkylsulfinyl” refers to a C1-C6-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-methylpentylsulfinyl, 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.


The terms “alkylsulfonyl” and “alkyl-S(O)k” (wherein k is 2) are equivalent and, as used herein, denote an alkyl group, as defined above, attached via a sulfonyl [S(O)2] group. The term “C1-C2-alkylsulfonyl” refers to a C1-C2-alkyl group, as defined above, attached via a sulfonyl [S(O)2] group. The term “C1-C4-alkylsulfonyl” refers to a C1-C4-alkyl group, as defined above, attached via a sulfonyl [S(O)2] group. The term “C1-C6-alkylsulfonyl” refers to a C1-C6-alkyl group, as defined above, attached via a sulfonyl [S(O)2] group. C1-C2-alkylsulfonyl is methyl-sulfonyl 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.


The term “alkylthio-alkyl” as used herein, refers to a straight-chain or branched alkyl group, as defined above, where one hydrogen atom is replaced by an alkylthio group, as defined above. The term “C1-C4-alkylthio-C1-C4-alkyl” as used herein, refers to a straight-chain or branched alkyl group having 1 to 4 carbon atoms, as defined above, where one hydrogen atom is replaced by a C1-C4-alkylthio group, as defined above. Examples are methylthiomethyl, ethyl-thiomethyl, propylthiomethyl, isopropylthiomethyl, n-butylthiomethyl, sec-butylthiomethyl, isobu-tylthiomethyl, tert-butylthiomethyl, 1-methylthioethyl, 1-ethylthioethyl, 1-propylthioethyl, 1-isopropylthioethyl, 1-n-butylthioethyl, 1-sec-butylthioethyl, 1-isobutylthioethyl, 1-tert-butylthioethyl, 2-methylthioethyl, 2-ethylthioethyl, 2-propylthioethyl, 2-isopropylthioethyl, 2-n-butylthioethyl, 2-sec-butylthioethyl, 2-isobutylthioethyl, 2-tert-butylthioethyl, 1-methylthiopropyl, 1-ethylthiopropyl, 1-propylthiopropyl, 1-isopropylthiopropyl, 1-n-butylthiopropyl, 1-sec-butylthiopropyl, 1-isobutylthiopropyl, 1-tert-butylthiopropyl, 2-methylthiopropyl, 2-ethylthiopropyl, 2-propylthiopropyl, 2-isopropylthiopropyl, 2-n-butylthiopropyl, 2-sec-butylthiopropyl, 2-isobutylthiopropyl, 2-tert-butylthiopropyl, 3-methylthiopropyl, 3-ethylthiopropyl, 3-propylthiopropyl, 3-isopropylthiopropyl, 3-n-butylthiopropyl, 3-sec-butylthiopropyl, 3-isobutylthiopropyl, 3-tert-butylthiopropyl and the like.


The term “alkylthio-alkylthio” as used herein, refers to an alkylthio group, as defined above, where one hydrogen atom is replaced by an alkylthio group, as defined above. The term “C1-C4-alkylthio-C1-C4-alkylthio” as used herein, refers to an alkylthio group having 1 to 4 carbon atoms, as defined above, where one hydrogen atom is replaced by a C1-C4-alkylthio group, as defined above. Examples are methylthiomethylthio, ethylthiomethylthio, propylthiomethylthio, isopropylthiomethylthio, n-butylthiomethylthio, sec-butylthiomethylthio, isobutylthiomethylthio, tert-butylthiomethylthio, 1-methylthioethylthio, 1-ethylthioethylthio, 1-propylthioethylthio, 1-isopropylthioethylthio, 1-n-butylthioethylthio, 1-sec-butylthioethylthio, 1-isobutylthioethylthio, 1-tert-butylthioethylthio, 2-methylthioethylthio, 2-ethylthioethylthio, 2-propylthioethylthio, 2-isopropylthioethylthio, 2-n-butylthioethylthio, 2-sec-butylthioethylthio, 2-isobutylthioethylthio, 2-tert-butylthioethylthio, 1-methylthiopropylthio, 1-ethylthiopropylthio, 1-propylthiopropylthio, 1-isopropylthiopropylthio, 1-n-butylthiopropylthio, 1-sec-butylthiopropylthio, 1-isobutylthiopropylthio, 1-tert-butylthiopropylthio, 2-methylthiopropylthio, 2-ethylthiopropylthio, 2-propylthiopropylthio, 2-isopropylthiopropylthio, 2-n-butylthiopropylthio, 2-sec-butylthiopropylthio, 2-isobutylthiopropylthio, 2-tert-butylthiopropylthio, 3-methylthiopropylthio, 3-ethylthiopropylthio, 3-propylthiopropylthio, 3-isopropylthiopropylthio, 3-n-butylthiopropylthio, 3-sec-butylthiopropylthio, 3-isobutylthiopropylthio, 3-tert-butylthiopropylthio and the like.


The term “alkylamino” as used herein denotes in each case a group R*HN—, wherein R* is a straight-chain or branched alkyl group usually having from 1 to 6 carbon atoms (=C1-C6-alkylamino), preferably 1 to 4 carbon atoms (=C1-C4-alkylamino) or 1 to 3 carbon atoms (=C1-C3-alkylamino). Examples of C1-C3-alkylamino are methylamino, ethylamino, n-propylamino and isopropylamino. Examples of C1-C4-alkylamino are, in addition to those mentioned for C1-C3-alkylamino, n-butylamino, 2-butylamino, iso-butylamino and tert-butylamino.


The term “dialkylamino” as used herein denotes in each case a group R*RoN—, wherein R* and Ro, independently of each other, are a straight-chain or branched alkyl group each usually having from 1 to 6 carbon atoms (=di-(C1-C6-alkyl)-amino), preferably 1 to 4 carbon atoms (=di-(C1-C4-alkyl)-amino) or 1 to 3 carbon atoms (=di-(C1-C3-alkyl)-amino). Examples of a di-(C1-C3-alkyl)-amino group are dimethylamino, diethylamino, dipropylamino, methyl-ethyl-amino, methyl-propyl-amino, methyl-isopropylamino, ethyl-propyl-amino, ethyl-isopropylamino, and the like. Examples of a di-(C1-C4-alkyl)-amino group are dimethylamino, diethylamino, dipropylamino, dibutylamino, methyl-ethyl-amino, methyl-propyl-amino, methyl-isopropylamino, methyl-butylamino, methyl-isobutyl-amino, ethyl-propyl-amino, ethyl-isopropylamino, ethyl-butyl-amino, ethyl-isobutyl-amino, and the like.


The substituent “oxo” replaces a CH2 group by a C(═O) group.


The suffix “-carbonyl” in a group denotes in each case that the group is bound to the remainder of the molecule via a carbonyl C═O group. This is the case e.g. in alkylcarbonyl, haloalkylcarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxycarbonyl, haloalkoxycarbonyl.


The term “alkylcarbonyl” denotes an alkyl group, as defined above, attached via a carbonyl [C(═O)] group to the remainder of the molecule. C1-C3-Alkylcarbonyl is a C1-C3-alkyl group, as defined above, attached via a carbonyl [C(═O)] group to the remainder of the molecule. C1-C4-Alkylcarbonyl is a C1-C4-alkyl group, as defined above, attached via a carbonyl [C(═O)] group to the remainder of the molecule. Examples for C1-C3-alkylcarbonyl are acetyl (methylcarbonyl), propionyl (ethylcarbonyl), propylcarbonyl and isopropylcarbonyl. Examples for C1-C4-alkylcarbonyl are acetyl (methylcarbonyl), propionyl (ethylcarbonyl), propylcarbonyl, isopropyl-carbonyl n-butylcarbonyl and the like.


Alkylene or alkanediyl is a linear or branched divalent alkyl radical. C1-C3-Alkylene or C1-C3-alkanediyl is a linear or branched divalent alkyl radical having 1, 2 or 3 carbon atoms. Examples are —CH2—, —CH2CH2—, —CH(CH3)—, —CH2CH2CH2—, —CH(CH3)CH2—, —CH2CH(CH3)— and —C(CH3)2—. C1-C4-Alkylene or C1-C4-alkanediyl is a linear or branched divalent alkyl radical having 1, 2, 3 or 4 carbon atoms. Examples are —CH2—, —CH2CH2—, —CH(CH3)—, —CH2CH2CH2—, —CH(CH3)CH2—, —CH2CH(CH3)—, —C(CH3)2—, —CH2CH2CH2CH2—, —CH(CH3)CH2CH2—, —CH2CH2CH(CH3)—, —C(CH3)2CH2—, and —CH2C(CH3)2—. Examples for linear C1-C4-alkylene or C1-C4-alkanediyl are —CH2—, —CH2CH2—, —CH2CH2CH2— and —CH2CH2CH2CH2—. C2-C4-Alkylene or C2-C4-alkanediyl is a linear or branched divalent alkyl radical having 2, 3 or 4 carbon atoms. Examples are —CH2CH2—, —CH(CH3)—, —CH2CH2CH2—, —CH(CH3)CH2—, —CH2CH(CH3)—, —C(CH3)2—, —CH2CH2CH2CH2—, —CH(CH3)CH2CH2—, —CH2CH2CH(CH3)—, —C(CH3)2CH2—, and —CH2C(CH3)2—. C3-C5-Alkylene or C3-C5-alkanediyl is a linear or branched divalent alkyl radical having 3, 4 or 5 carbon atoms. Examples are —CH2CH2CH2—, —CH(CH3)CH2—, —CH2CH(CH3)—, —C(CH3)2—, —CH2CH2CH2CH2—, —CH(CH3)CH2CH2—, —CH2CH2CH(CH3)—, —C(CH3)2CH2—, —CH2C(CH3)2—, —(CH2)5— and the like.


The term “aryl” as used herein refers to a mono-, bi- or tricyclic aromatic hydrocarbon radical such as phenyl or naphthyl, in particular phenyl.


Phenoxy is a phenyl ring bound via an oxygen atom.


The term “het(ero)aryl” as used herein refers to a mono-, bi- or tricyclic heteroaromatic hydrocarbon radical, preferably to a monocyclic heteroaromatic radical, such as pyridyl, pyrimidyl and the like.


If not specified otherwise, the heterocyclic rings or heterocyclyl may be saturated, partially unsaturated or maximally unsaturated.


The term “3-, 4-, 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, unsaturated or aromatic heterocycle containing 1, 2, 3 or 4 heteroatoms as ring members selected from the groups consisting of N, O and S″ as used herein denotes monocyclic or bicyclic radicals, the monocyclic or bicyclic radicals being saturated, unsaturated or aromatic where N can optionally be oxidized, i.e. in the form of an N-oxide, and S can also optionally be oxidized to various oxidation states, i.e. as SO or SO2. An unsaturated heterocycle contains at least one C—C and/or C—N and/or N—N double bond(s). Partially unsaturated rings contain less than the maximum number of C—C and/or C—N and/or N—N double bond(s) allowed by the ring size. A fully (or maximally) unsaturated heterocycle contains as many conjugated C—C and/or C—N and/or N—N double bonds as allowed by the size(s) of the ring(s). Maximally unsaturated 5- or 6-membered heteromonocyclic rings are generally aromatic. Exceptions are maximally unsaturated 6-membered rings containing O, S, SO and/or SO2 as ring members, such as pyran and thiopyran, which are not aromatic. An aromatic monocyclic heterocycle is thus a fully unsaturated 5-membered monocyclic heterocycle or a fully unsaturated 6-membered monocyclic heterocycle containing one or more nitrogen atoms as ring members and no O, S, SO and/or SO2 as ring members. An aromatic bicyclic heterocycle is an 8-, 9- or 10-membered bicyclic heterocycle consisting of a 5- or 6-membered heteroaromatic ring which is fused to a phenyl ring or to another 5- or 6-membered heteroaromatic ring. The heterocycle may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member. As a matter of course, the heterocyclic ring contains at least one carbon ring atom. If the ring contains more than one O ring atom, these are not adjacent.


Examples of a 3-, 4-, 5- or 6-membered monocyclic saturated heterocycle include: oxirane-2-yl, aziridine-1-yl, aziridine-2-yl, oxetan-2-yl, azetidine-1-yl, azetidine-2-yl, azetidine-3-yl, thietane-1-yl, thietan-2-yl, thietane-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothien-2-yl, tetrahydrothien-3-yl, pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-3-yl, pyrazolidin-1-yl, pyrazolidin-3-yl, pyrazolidin-4-yl, pyrazolidin-5-yl, imidazolidin-1-yl, imidazolidin-2-yl, imidazolidin-4-yl, oxazolidin-2-yl, oxazolidin-3-yl, oxazolidin-4-yl, oxazolidin-5-yl, isoxazolidin-2-yl, isoxazolidin-3-yl, isoxazolidin-4-yl, isoxazolidin-5-yl, thiazolidin-2-yl, thiazolidin-3-yl, thiazolidin-4-yl, thiazolidin-5-yl, isothiazolidin-2-yl, isothiazolidin-3-yl, isothiazolidin-4-yl, isothiazolidin-5-yl, 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-1-yl, 1,3,4-triazolidin-2-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 1,3-dioxan-5-yl, 1,4-dioxan-2-yl, piperidin-1-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, hexahydropyridazin-3-yl, hexahydro-pyridazin-4-yl, hexahydropyrimidin-2-yl, hexahydropyrimidin-4-yl, hexahydropyrimidin-5-yl, piperazin-1-yl, piperazin-2-yl, 1,3,5-hexahydrotriazin-1-yl, 1,3,5-hexahydrotriazin-2-yl and 1,2,4-hexahydrotriazin-3-yl, morpholin-2-yl, morpholin-3-yl, morpholin-4-yl, thiomorpholin-2-yl, thiomorpholin-3-yl, thiomorpholin-4-yl, 1-oxothiomorpholin-2-yl, 1-oxothiomorpholin-3-yl, 1-oxothiomorpholin-4-yl, 1,1-dioxothiomorpholin-2-yl, 1,1-dioxothiomorpholin-3-yl, 1,1-dioxothiomorpholin-4-yl and the like.


Examples of a 5- or 6-membered monocyclic partially unsaturated heterocycle 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 and 1,2,4-di- or tetrahydrotriazin-3-yl.


A 5- or 6-membered monocyclic fully unsaturated (including aromatic) heterocyclic ring is e.g. a 5- or 6-membered monocyclic fully unsaturated (including aromatic) heterocyclic ring. Examples are: 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 1-imidazolyl, 2-imidazolyl, 4-imidazolyl, 1,3,4-triazol-1-yl, 1,3,4-triazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 1-oxopyridin-2-yl, 1-oxopyridin-3-yl, 1-oxopyridin-4-yl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl.


Examples of a 5- or 6-membered heteroaromatic ring fused to a phenyl ring or to a 5- or 6-membered heteroaromatic radical include benzofuranyl, benzothienyl, indolyl, indazolyl, benzimidazolyl, benzoxathiazolyl, benzoxadiazolyl, benzothiadiazolyl, benzoxazinyl, chinolinyl, iso-chinolinyl, purinyl, 1,8-naphthyridyl, pteridyl, pyrido[3,2-d]pyrimidyl or pyridoimidazolyl and the like.


If two radicals bound on the same nitrogen atom (for example R2a and R2b or R3c and R3d or R3e and R3f or R3g and R3h or R4e and R4f or R4g and R4h), together with the nitrogen atom to which they are bound, form a 4-, 5-, 6-, 7- or 8-membered, saturated or unsaturated N-bound heterocyclic radical which may contain as a ring member a further heteroatom selected from the group consisting of O, S and N, this is for example azetidin-1-yl, pyrrolidine-1-yl, pyrazolidin-1-yl, imidazolidin-1-yl, oxazolidin-3-yl, thiazolidin-3-yl, isoxazolidin-2-yl, isothiazolin-2-yl, [1,2,3]-triazolidin-1-yl, [1,2,3]-triazolidin-2-yl, [1,2,4]-triazolidin-1-yl, [1,2,4]-triazolidin-4-yl, [1,2,3]-oxadiazolidin-2-yl, [1,2,3]-oxadiazolidin-3-yl, [1,2,5]-oxadiazolidin-2-yl, [1,2,4]-oxadiazolidin-2-yl, [1,2,4]-oxadiazolidin-4-yl, [1,3,4]-oxadiazolidin-3-yl, [1,2,3]-thiadiazolidin-2-yl, [1,2,3]-thiadiazolidin-3-yl, [1,2,5]-thiadiazolidin-2-yl, [1,2,4]-thiadiazolidin-2-yl, [1,2,4]-thiadiazolidin-4-yl, [1,3,4]-thiadiazolidin-3-yl, piperdin-1-yl, piperazine-1-yl, morpholin-1-yl, thiomorpholin-1-yl, 1-oxothiomorpholin-1-yl, 1,1-dioxothiomorpholin-1-yl, azepan-1-yl, 1,4-diazepan-1-yl, pyrrolin-1-yl, pyrazolin-1-yl, imidazolin-1-yl, oxazolin-3-yl, isoxazolin-2-yl, thiazolin-3-yl, isothiazolin-1-yl, 1,2-dihydropyridin-1-yl, 1,2,3,4-tetrahydropyridin-1-yl, 1,2,5,6-tetrahydropyridin-1-yl, 1,2-dihydropyridazin, 1,6-dihydropyridazin, 1,2,3,4-tetrahydropyridazin-1-yl, 1,2,5,6-tetrahydropyridazin-1-yl, 1,2-dihydropyrimidin, 1,6-dihydropyrimidin, 1,2,3,4-tetrahydropyrimidin-1-yl, 1,2,5,6-tetrahydropyrimidin-1-yl, 1,2-dihydropyrazin-1-yl, 1,2,3,4-tetrahydropyrazin-1-yl, 1,2,5,6-tetrahydropyrazin-1-yl, pyrrol-1-yl, pyrazol-1-yl, imidazol-1-yl, [1,2,3]-1H-triazol-1-yl, [1,2,3]-2H-triazol-2-yl, [1,2,4]-1H-triazol-1-yl and [1,2,4]-4H-triazol-4-yl.


The remarks made below as to preferred embodiments of the variables (substituents) of the compounds of formula I are valid on their own as well as preferably in combination with each other, as well as in combination with the stereoisomers, salts, or tautomers thereof.


The remarks made below concerning preferred embodiments of the variables further are valid on their own as well as preferably in combination with each other concerning the compounds of formulae I, where applicable, as well as concerning the uses and methods according to the invention and the composition according to the invention.


Preferred compounds according to the invention are compounds of formula I, including its stereoisomers, or an N-oxide or salt thereof, wherein the salt is an agriculturally suitable salt.


According to one group 1 of embodiments of the invention the variable Q in the compounds of formula I is Q1:




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where # in formula Q1 indicates the point of attachment to the nitrogen atom. Compounds of formula I wherein Q is Q1 have the following formula I.A, where the variables R1, Z2, R2a, R2b, R2c, R3, R4, R5, R6a and R7 are as defined herein:




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According to another group 2 of embodiments of the invention the variable Q in the compounds of formula I is Q2:




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where # in formula Q2 indicates the point of attachment to the nitrogen atom. Compounds of formula I wherein Q is Q2 have the following formula I.B, where the variables R1, Z2, R2a, R2b, R2c, R3, R4, R5, R6b and R7 are as defined herein:




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According to a further group 3 of embodiments of the invention the variable Q in the compounds of formula I is Q3:




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where # in formula Q3 indicates the point of attachment to the nitrogen atom. Compounds of formula I wherein Q is Q3 have the following formula I.C, where the variables R1, Z2, R2a, R2b, R2c, R3, R4, R5, R6c and R7 are as defined herein:




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According to yet a further group 4 of embodiments of the invention the variable Q in the compounds of formula I is Q4:




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where # in formula Q3 indicates the point of attachment to the nitrogen atom. Compounds of formula I wherein Q is Q4 have the following formula I.D, where the variables R1, Z2, R2a, R2b, R2c, R3, R4, R5, R6d and R7 are as defined herein:




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Amongst the compounds of formula I, their N-oxides and their agriculturally suitable salts, particular preference is given to the compounds of group 1 of embodiments.


Amongst the compounds of formula I, their N-oxides and their agriculturally suitable salts, particular preference is also given to the compounds of group 2 of embodiments.


Amongst the compounds of formula I, their N-oxides and their agriculturally suitable salts, particular preference is also given to the compounds of group 4 of embodiments.


Specifically, the compounds of formula I are the compounds of formula I.A wherein Q is Q1 (group 1).


The compounds of formula I of the present invention are preferably selected from compounds of the formulae I.A, I.B, I.C and I.D, their N-oxides and their agriculturally suitable salts, where the variables R1, Z2, R2a, R2b, R2c, R3, R4, R5, R7 and R6a, R6b, R6c or R6d are as defined herein and in particular have the preferred meanings given herein below. The following preferred meanings apply to each of groups 1, 2, 3 and 4 of embodiments in the same manner.


A particular group of compounds according to the invention are compounds of formulae I, I.A, I.B, I.C and I.D, their N-oxides and their salts, wherein Z2 is a covalent bond, i.e. a covalent single bond, and R7 is H. These compounds are hereinafter termed compounds of the formulae I′, I.A′, I.B′, I.C′ and I.D′, respectively.




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Another particular group of compounds according to the invention are compounds of formulae I, I.A, I.B, I.C and I.D, their N-oxides and their salts, wherein Z2 is a bivalent radical, which is in particular linear C1-C4-alkanediyl and especially —CH2— or —CH2CH2—.


Preferred compounds according to the invention are compounds of formulae I, I.A, I.B, I.C and I.D, and likewise compounds of the formulae I′, I.A′, I.B′, I.C′ and I.D′, their N-oxides and their salts, wherein R1 is selected from the group consisting of cyano, halogen, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-haloalkoxy-C1-C4-alkyl, C1-C6-alkoxy, C1—C4-alkoxy-C1-C4-alkoxy-Z1, R1b—S(O)k—Z1, where k and Z1 are as defined herein and where R1b is as defined above and in particular selected from the group consisting of C1-C4-alkyl and C1-C4-haloalkyl. In this context Z1 is in particular a covalent bond.


More preferably, R1 in formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′ is selected from the group consisting of halogen, nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkoxy-Z1 and R1b—S(O)k—Z1, where k and Z1 are as defined herein and where R1b is as defined above and in particular selected from the group consisting of C1-C4-alkyl and C1-C4-haloalkyl. In this context Z1 is in particular a covalent bond.


In particular, R1 in formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′ is selected from the group consisting of halogen, nitro, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio, C1-C4-haloalkylthio and C1-C4-alkylsulfonyl. Specifically R1 in formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′ is selected from the group consisting of F, Cl, Br, I, nitro, CH3, CF3, OCH3, SCH3, SCF3, SO2CH3 and CH2OCH2CH2OCH3. More specifically R1 in formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′ is selected from the group consisting of F, Cl, Br, I, nitro, CH3, CF3, OCH3, SCH3 and SO2CH3, even more specifically R1 in formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′ is selected from the group consisting of C1, Br, CH3, CF3 and OCH3, and especially R1 in formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′ is Cl or CH3.


In another specific embodiment, R1 in formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′ is selected from the group consisting of halogen, C1-C4-alkyl and C1-C4-alkoxy. More specifically, R1 in formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′ is selected from the group consisting of Cl, Br, CH3, and OCH3, more specifically from Cl, CH3, and OCH3, and is very specifically Cl or CH3.


Preferred compounds according to the invention are compounds of formulae I, I.A, I.B, I.C and I.D, and likewise compounds of the formulae I′, I.A′, I.B′, I.C′ and I.D′, their N-oxides and their salts, wherein R2a is selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-alkoxy, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, C1-C6-haloalkyl, phenyl, benzyl, and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1, 2, 3 or 4 heteroatoms as ring members which are selected from the group consisting of O, N and S, where phenyl, benzyl and heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4 groups R21 which are identical or different and where R21 is preferably selected from the group consisting of halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy and where R21 is in particular selected from the group consisting of halogen, C1-C4-alkyl, fluorinated C1-C2-alkyl, C1-C4-alkoxy and fluorinated C1-C2-alkoxy and especially from the group consisting of halogen, methyl and methoxy.


Preference is given to compounds of the invention, where the radical R2a in formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′ is different from hydrogen.


In the context of R2a, heterocyclyl is in particular a 5- or 6-membered monocyclic saturated or aromatic heterocycle which contains 1, 2 or 3 heteroatoms as ring members which are selected from the group consisting of O, N and S. In this context, heterocyclyl is in particular a 5- or 6-membered monocyclic aromatic heterocycle which contains 1 or 2 heteroatoms as ring members which are selected from the group consisting of O, N and S;


In formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′, R2a is in particular selected from the group consisting of C1-C4-alkyl, C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkyl-methyl, fluorinated C1-C4-alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1, 2, 3 or 4 radicals R21 which are identical or different and where R21 is preferably selected from the group consisting of halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy and where R21 is in particular selected from the group consisting of halogen, C1-C4-alkyl, fluorinated C1-C2-alkyl, C1-C4-alkoxy and fluorinated C1-C2-alkoxy and especially from the group consisting of halogen, methyl and methoxy.


In formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′, R2a is more particularly selected from the group consisting of C1-C4-alkyl, C3-C7-cycloalkyl, fluorinated C1-C4-alkyl, C1-C4-alkoxy and phenyl, where phenyl is unsubstituted or substituted by 1 or 2 groups R21 which are identical or different and which are preferably selected from the group consisting of halogen, C1-C4-alkyl, fluorinated C1-C2-alkyl, C1-C4-alkoxy and fluorinated C1-C2-alkoxy and especially from the group consisting of halogen, methyl and methoxy.


In formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′, R2a is even more particularly selected from the group consisting of C1-C4-alkyl, fluorinated C1-C2-alkyl, C3-C4-cycloalkyl, and phenyl which is unsubstituted or substituted by 1, 2 or 3 radicals R21 selected from the group consisting of halogen, C1-C4-alkyl, fluorinated C1-C2-alkyl, C1-C4-alkoxy and fluorinated C1-C2-alkoxy and where phenyl is in particular unsubstituted or substituted by 1, 2 or 3 radicals selected from the group consisting of halogen, methyl and methoxy.


In formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′, R2a is especially selected from the group consisting of methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2—, CF3CH2—, CH3O—, 4-Cl-phenyl, 4-methoxyphenyl, 4-methylphenyl and 2,6-dimethylphenyl.


In another even more particular embodiment, in formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′, R2a is selected from the group consisting of C1-C6-alkyl, C3-C6-cycloalkyl, C1-C4-haloalkyl and phenyl, where phenyl is unsubstituted or substituted by 1, 2, 3 or 4 C1-C4-alkyl groups which are identical or different. More preferably, R2a is selected from the group consisting of C1-C4-alkyl, C3-C6-cycloalkyl, fluorinated C1-C4-alkyl and phenyl which is unsubstituted or substituted by 1, 2, 3 or 4 methyl groups. Even more preferably, R2a is selected from the group consisting of C1-C4-alkyl, C3-C4-cycloalkyl, fluorinated C1-C2-alkyl and phenyl which is unsubstituted or substituted by 1, 2 or 3 methyl groups. Specifically, R2a is selected from the group consisting of C1-C4-alkyl, cyclopropyl, fluorinated C1-C2-alkyl and phenyl which is unsubstituted or substituted by 1 or 2 methyl groups.


Preferred compounds according to the invention are compounds of formulae I, I.A, I.B, I.C and I.D, and likewise compounds of the formulae I′, I.A′, I.B′, I.C′ and I.D′, their N-oxides and their salts, wherein R2b is selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-alkoxy, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, C1-C6-haloalkyl, phenyl, benzyl, and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1, 2, 3 or 4 heteroatoms as ring members which are selected from the group consisting of O, N and S, where phenyl, benzyl and heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4 groups R21 which are identical or different and where R21 is preferably selected from the group consisting of halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy and where R21 is in particular selected from the group consisting of halogen, C1-C4-alkyl, fluorinated C1-C2-alkyl, C1-C4-alkoxy and fluorinated C1-C2-alkoxy and especially from the group consisting of halogen, methyl and methoxy.


Preference is given to compounds of the invention, where the radical R2b in formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′ is different from hydrogen.


In the context of R2b, heterocyclyl is in particular a 5- or 6-membered monocyclic saturated or aromatic heterocycle which contains 1, 2 or 3 heteroatoms as ring members which are selected from the group consisting of O, N and S. In this context, heterocyclyl is in particular a 5- or 6-membered monocyclic aromatic heterocycle which contains 1 or 2 heteroatoms as ring members which are selected from the group consisting of O, N and S.


In formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′, R2b is in particular selected from the group consisting of hydrogen, C1-C4-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-methyl and fluorinated C1-C4-alkyl.


In formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′, R2b is more particularly selected from the group consisting of hydrogen, C1-C4-alkyl, C3-C7-cycloalkyl and fluorinated C1-C4-alkyl.


In formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′, R2b is even more particularly selected from the group consisting of hydrogen, C1-C4-alkyl, fluorinated C1-C2-alkyl and C3-C4-cycloalkyl.


In formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′, R2b is especially selected from the group consisting of hydrogen, methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2— and CF3CH2—.


In an alternative particular embodiment, in formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′, R2b is selected from the group consisting of hydrogen, C1-C4-alkyl and C3-C6-cycloalkyl, and more preferably from hydrogen, C1-C3-alkyl and C3-C4-cycloalkyl. Specifically, R2b is selected from the group consisting of hydrogen, C1-C3-alkyl and cyclopropyl.


Likewise, preference is given to the compounds of formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′, their N-oxides and their salts, wherein R2a and R2b, together with the nitrogen atom to which they are bound, form a 4-, 5-, 6- or 7-membered, saturated or unsaturated heterocyclic radical which may contain as a ring member a further heteroatom selected from the group consisting of O, S and N and which is unsubstituted or may carry 1, 2, 3 or 4 groups R2d which are identical or different and in particular selected from the group consisting of ═O, OH, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy. Amongst these, particular preference is given to those compounds where in formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′ the variables R2a and R2b, together with the nitrogen atom to which they are bound, may form a 5- or 6-membered, saturated or unsaturated heterocyclic radical which may contain as a ring member a further heteroatom selected from the group consisting of O, S and N and which is unsubstituted or may carry 1, 2, 3 or 4 groups R2d which are identical or different and in particular selected from the group consisting of ═O, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy. Amongst these, special preference is given to those compounds where in formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′ the variables, R2a and R2b, together with the nitrogen atom to which they are bound, form 4-morpholinyl, 4-thiomorpholinyl, 1-piperidinyl and 1-pyrrolidinyl, where 4-morpholinyl, 4-thiomorpholinyl, 1-piperidinyl and 1-pyrrolidinyl are unsubstituted or carry 1, 2, 3 or 4 groups R2d which are selected from the group consisting of C1-C4-alkyl and fluorinated C1-C4-alkyl, preferably from methyl, ethyl and trifluoromethyl. Specifically, R2a and R2b, together with the nitrogen atom to which they are bound, form (unsubstituted) 4-morpholinyl.


Preferred compounds according to the invention are compounds of formulae I, I.A, I.B, I.C and I.D, and likewise compounds of the formulae I′, I.A′, I.B′, I.C′ and I.D′, their N-oxides and their salts, wherein R2c is hydrogen or C1-C4-alkyl and wherein R2c is especially hydrogen.


In formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′, the combination of R2a, R2b and R2 is in particular as follows:

  • R2a is selected from the group consisting of C1-C4-alkyl, C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkyl-methyl, fluorinated C1-C4-alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1, 2, 3 or 4 radicals R21 which are identical or different and where R21 is preferably selected from the group consisting of halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy and where R21 is in particular selected from the group consisting of halogen, C1-C4-alkyl, fluorinated C1-C2-alkyl, C1-C4-alkoxy and fluorinated C1-C2-alkoxy and especially from the group consisting of halogen, methyl and methoxy; hydrogen, C1-C4-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-methyl and fluorinated C1-C4-alkyl,
    • R2a is more particularly selected from the group consisting of C1-C4-alkyl, C3-C7-cycloalkyl, fluorinated C1-C4-alkyl, C1-C4-alkoxy and phenyl, where phenyl is unsubstituted or substituted by 1 or 2 groups R21 which are identical or different and which are preferably selected from the group consisting of halogen, C1-C4-alkyl, fluorinated C1-C2-alkyl, C1-C4-alkoxy and fluorinated C1-C2-alkoxy and especially from the group consisting of halogen, methyl and methoxy,
    • R2a is even more particularly selected from the group consisting of C1-C4-alkyl, fluorinated C1-C2-alkyl, C3-C4-cycloalkyl, and phenyl which is unsubstituted or substituted by 1, 2 or 3 radicals R21 selected from the group consisting of halogen, C1-C4-alkyl, fluorinated C1-C2-alkyl, C1-C4-alkoxy and fluorinated C1-C2-alkoxy and where phenyl is in particular unsubstituted or substituted by 1, 2 or 3 radicals selected from the group consisting of halogen, methyl and methoxy,
    • R2a is especially selected from the group consisting of methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2—, CF3CH2—, CH3O—, 4-Cl-phenyl, 4-methoxyphenyl, 4-methylphenyl and 2,6-dimethylphenyl;
  • R2b is selected from the group consisting of hydrogen, C1-C4-alkyl, C3-C7-cycloalkyl and fluorinated C1-C4-alkyl, in particular selected from the group consisting of hydrogen, C1-C4-alkyl, fluorinated C1-C2-alkyl and C3-C4-cycloalkyl and especially selected from the group consisting of hydrogen, methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2— and CF3CH2—;
  • or
  • R2a and R2b, together with the nitrogen atom to which they are bound, may form a 5- or 6-membered, saturated or unsaturated heterocyclic radical which may contain as a ring member a further heteroatom selected from the group consisting of O, S and N and which is unsubstituted or may carry 1, 2, 3 or 4 groups R2d which are identical or different and in particular selected from the group consisting of ═O, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy, and where R2a and R2b, together with the nitrogen atom to which they are bound, in particular form 4-morpholinyl, 4-thiomorpholinyl, 1-piperidinyl and 1-pyrrolidinyl, where 4-morpholinyl, 4-thiomorpholinyl, 1-piperidinyl and 1-pyrrolidinyl are unsubstituted or carry 1, 2, 3 or 4 groups R2d which are selected from the group consisting of C1-C4-alkyl and fluorinated C1-C4-alkyl, preferably from methyl, ethyl and trifluoromethyl.
  • R2c is hydrogen or C1-C4-alkyl and especially hydrogen.


More particularly, in formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′, the combination of R2a, R2b and R2c is as follows:

  • R2a is selected from the group consisting of C1-C6-alkyl, C3-C6-cycloalkyl, C1-C4-haloalkyl and phenyl, where phenyl is unsubstituted or substituted by 1, 2, 3 or 4 C1-C4-alkyl groups which are identical or different;
  • R2b is selected from the group consisting of hydrogen, C1-C4-alkyl and C3-C6-cycloalkyl; or
  • R2a and R2b, together with the nitrogen atom to which they are bound, form a 5- or 6-membered saturated heterocyclic radical which may contain as a ring member a further heteroatom selected from O, S and N, and which is unsubstituted or carries 1, 2, 3 or 4 groups R2d which are selected from the group consisting of C1-C4-alkyl and fluorinated C1-C4-alkyl; and
  • R2c is hydrogen or C1-C4-alkyl and especially hydrogen.


Even more particularly, in formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′, the combination of R2a, R2b and R2c is as follows:

  • R2a is selected from the group consisting of C1-C4-alkyl, C3-C6-cycloalkyl, fluorinated C1-C4-alkyl and phenyl which is unsubstituted or substituted by 1, 2, 3 or 4 methyl groups;
  • R2b is selected from the group consisting of hydrogen, C1-C4-alkyl and C3-C6-cycloalkyl; or
  • R2a and R2b, together with the nitrogen atom to which they are bound, form a 4-morpholinyl ring; and
  • R2c is hydrogen or C1-C4-alkyl and especially hydrogen.


Specifically, in formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′, the combination of R2a, R2b and R2c is as follows:

  • R2a is selected from the group consisting of C1-C4-alkyl, C3-C4-cycloalkyl, fluorinated C1-C2-alkyl and phenyl which is unsubstituted or substituted by 1, 2 or 3 methyl groups;
  • R2b is selected from the group consisting of hydrogen, C1-C3-alkyl and C3-C4-cycloalkyl; or
  • R2a and R2b, together with the nitrogen atom to which they are bound, form a 4-morpholinyl ring; and
  • R2c is hydrogen or C1-C4-alkyl and especially hydrogen.


Preferred compounds according to the invention are compounds of formulae I, I.A, I.B, I.C and I.D, and likewise compounds of the formulae I′, I.A′, I.B′, I.C′ and I.D′, their N-oxides and their salts, wherein R3 is selected from the group consisting of hydrogen, cyano, halogen, nitro, C1-C6-alkyl, C1-C8-haloalkyl, C1-C4-alkoxy, C1-C8-haloalkoxy-Z3, C2-C4-alkenyl, C2-C4-alkynyl, C2-C4-alkenyloxy, C2-C4-alkynyloxy and R3b—S(O)k—Z3, where the variables k, R3b and Z3 have one of the herein defined meanings; more preferably, R3 is selected from the group consisting of halogen, nitro, C1-C6-alkyl, C1-C8-haloalkyl, C1-C8-haloalkoxy-Z3, and R3b—S(O)k—Z3, where the variables k, R3b and Z3 have one of the herein defined meanings; even more preferably, R3 is selected from the group consisting of halogen, nitro, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-haloalkoxy, and R3b—S(O)k, where the variables k and R3b have one of the herein defined meanings.


In the context of R3, R3b is preferably selected from the group consisting of C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, C1-C6-haloalkyl, phenyl, and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1, 2, 3 or 4 heteroatoms as ring members which are selected from the group consisting of O, N and S, where phenyl and heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4 groups which are identical or different and selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy. More preferably, R3b is selected from the group consisting of C1-C4-alkyl, C3-C7-cycloalkyl, C1-C4-haloalkyl, and phenyl, where phenyl is unsubstituted or substituted by 1 or 2 groups which are identical or different and selected from the group consisting of halogen and C1-C4-alkoxy; Herein, particularly preferably, R3b is methyl, ethyl, cyclopropyl (cPr), CF3, CHF2CH2—, CF3CH2— or CF3FF2—.


In the context of R3, R3c is preferably selected from the group consisting of C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, C1-C6-haloalkyl, C1-C4-alkoxy, C1-C6-haloalkoxy, phenyl, and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1, 2, 3 or 4 heteroatoms as ring members which are selected from the group consisting of O, N and S, where phenyl and heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4 groups which are identical or different and selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy. More preferably, R3c is selected from the group consisting of C1-C4-alkyl, C1-C4-alkoxy, C3-C7-cycloalkyl, C1-C4-haloalkyl, and phenyl, where phenyl is unsubstituted or substituted by 1 or 2 groups which are identical or different and selected from the group consisting of halogen and C1-C4-alkoxy.


In the context of R3, R3d is preferably selected from the group consisting of C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, C1-C6-haloalkyl and phenyl where phenyl is unsubstituted or substituted by 1, 2, 3 or 4 groups which are identical or different and selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy; more preferably, R3d is selected from the group consisting of C1-C4-alkyl, C3-C7-cycloalkyl, and C1-C4-haloalkyl; particularly preferably, R3d is methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2— or CF3CH2—.


In the context of R3, Z3 is in particular a covalent bond or linear C1-C4-alkanediyl; preferably, Z3 is a covalent bond, —CH2— or —CH2CH2—.


In particular, R3 in formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′ is selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-haloalkoxy, C1-C4-alkylthio, C1—C4-haloalkylthio, C1-C4-alkyl-S(O), C1-C4-haloalkyl-S(O), C1-C4-alkyl-S(O)2, and C1-C4-haloalkyl-S(O)2.


More particularly, R3 in formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′ is selected from the group consisting of halogen, C1-C2-alkyl, C1-C2-haloalkyl, C1-C2-haloalkoxy, C1-C2-alkylthio, C1-C2-haloalkylthio, C1-C2-alkyl-S(O), C1-C2-haloalkyl-S(O), C1-C2-alkyl-S(O)2 and C1-C2-haloalkyl-S(O)2, especially from the group consisting of Cl, F, Br, I, CH3, CF3, CHF2, OCF3, OCHF2, SCH3, SCF3, SCHF2, S(O)CH3, S(O)CH2CH3, S(O)2CH3 and S(O)2CH2CH3, and more specifically R3 is Cl, Br, CF3, SCH3, S(O)CH3 or S(O)2CH3.


In an alternative more particular embodiment, R3 in formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′ is halogen, and is specifically Cl or Br.


Preferred compounds according to the invention are compounds of formulae I, I.A, I.B, I.C and I.D, and likewise compounds of the formulae I′, I.A′, I.B′, I.C′ and I.D′, their N-oxides and their salts, wherein R4 is selected from the group consisting of hydrogen, cyano, halogen, nitro, CH3, CHF2, and CF3, in particular from hydrogen, cyano, chlorine, fluorine and CH3.


Even more preferred compounds according to the invention are compounds of formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′, their N-oxides and their salts, wherein R4 is hydrogen, chlorine or fluorine.


Most preferred compounds according to the invention are compounds of formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′, their N-oxides and their salts, wherein R4 is hydrogen.


Preferred compounds according to the invention are compounds of formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′, their N-oxides and their salts, wherein R5 is selected from the group consisting of hydrogen, CHF2, CF3 and halogen. More preferably, R5 is hydrogen or halogen, in particular hydrogen, chlorine or fluorine, especially hydrogen or fluorine. Very specifically, R5 is fluorine.


Preferred compounds according to the invention are compounds of formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′, their N-oxides and their salts, wherein R6a, R6b, R6c, R6d are, independently of each other, selected from the group consisting of C1-C6-alkyl, C1-C4-alkoxy-C1-C4-alkyl, and phenyl. In particular, R6a, R6b, R6c, R6d are, independently of each other, selected from the group consisting of C1-C2-alkyl, C1-C2-alkoxy-C1-C2-alkyl, specifically from CH3, CH3CH2, CH3OCH2CH2 and CH3OCH2, more particularly from C1-C2-alkyl, and are specifically, independently of each other, CH3.


Preferred compounds according to the invention are compounds of formulae I, I.A, I.B, I.C and I.D, wherein R7 is hydrogen or C1-C4-alkyl and wherein R7 is especially hydrogen.


In the context of the present invention, the variables R11, R21, R22, R23, R24, R25, Z1, Z3, Z3a, Z4, Rb, R1b, R3b, R3c, R3d, R3e, R3f, R3g, R3h, R4b, R4c, R4d, R4e, R4f, R4g, R4h, Rk, Rz, n and k, independently of each other, preferably have one of the following meanings:


In particular, R11, R21 independently of each other are selected from the group consisting of halogen, C1-C4-alkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkoxy and C1-C6-haloalkyloxy, more preferably from halogen, C1-C4-alkyl, C3-C6-cycloalkyl, C1-C4-haloalkyl and C1-C4-alkoxy.


More preferably R11, R21 independently of each other are selected from the group consisting of halogen, C1-C4-alkyl, C3-C6-cycloalkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl and C1-C4-alkoxy-C1-C4-alkoxy; in particular from halogen, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-alkoxy-C1-C4-alkyl and C1-C4-alkoxy-C1-C4-alkoxy; and specifically from C1, F, Br, methyl, ethyl, methoxy and trifluoromethyl.


In particular, R22 is selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4-alkyl, phenyl, benzyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1, 2 or 3 heteroatoms as ring members which are selected from the group consisting of O, N and S, where the rings of phenyl, benzyl and heterocyclyl are unsubstituted or substituted by 1, 2 or 3 groups which are identical or different and selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl and C1-C4-alkoxy.


More preferably R22 is selected from hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1, 2 or 3 heteroatoms as ring members which are selected from the group consisting of O, N and S.


Especially, R22 is selected from the group consisting of hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C3-C6-cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered aromatic heterocyclic radical having 1 or 2 nitrogen atoms as ring members.


In particular, R23 is selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C3-C6-cycloalkyl and phenyl. More preferably R23 is selected from the group consisting of hydrogen, C1-C4-alkyl, C1-C4-haloalkyl and C3-C6-cycloalkyl; and in particular, R23 is selected from hydrogen, C1-C3-alkyl and C1-C3-haloalkyl.


R24 is in particular selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C3-C6-cycloalkyl and phenyl.


More preferably R24 is in particular selected from the group consisting of C1-C4-alkyl, C1-C4-haloalkyl and C3-C6-cycloalkyl; and in particular R23 is selected from the group consisting of C1-C3-alkyl and C1-C3-haloalkyl.


R25 is in particular selected from the group consisting of C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4-alkyl, phenyl, benzyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1, 2 or 3 heteroatoms as ring members which are selected from the group consisting of O, N and S, where the rings of phenyl, benzyl and heterocyclyl are unsubstituted or substituted by 1, 2 or 3 groups which are identical or different and selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl and C1-C4-alkoxy.


More preferably R25 is selected from the group consisting of C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1, 2 or 3 heteroatoms as ring members which are selected from the group consisting of O, N and S.


In particular, R25 is selected from C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C3-C7-cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered aromatic heterocyclic radical having 1 or 2 nitrogen atoms as ring members.


Z1, Z3, Z4, independently of each other are in particular selected from the group consisting of a covalent bond, methanediyl and ethanediyl, and in particular are a covalent bond.


Z3a is in particular selected from the group consisting of a covalent bond, C1-C2-alkanediyl, O—C1-C2-alkanediyl, C1-C2-alkanediyl-O and C1-C2-alkanediyl-O—C1-C2-alkanediyl; more preferably from a covalent bond, methanediyl, ethanediyl, O-methanediyl, O-ethanediyl, methanediyl-O, and ethanediyl-O; and in particular from a covalent bond, methanediyl and ethanediyl.


Rb, R1b, R3b, R4b independently of each other are in particular selected from the group consisting of C1-C6-alkyl, C3-C7-cycloalkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1, 2 or 3 heteroatoms as ring members which are selected from the group consisting of O, N and S, where phenyl and heterocyclyl are unsubstituted or substituted by 1, 2 or 3 groups which are identical or different and selected from the group consisting of halogen, C1-C4-alkyl, C1-C2-haloalkyl and C1-C2-alkoxy.


More preferably Rb, R1b, R3b, R4b independently of each other are selected from the group consisting of C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-haloalkyl, C2-C4-haloalkenyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1, 2 or 3 heteroatoms as ring members which are selected from the group consisting of O, N and S.


In particular, Rb, R1b, R3b, R4b independently of each other are selected from the group consisting of C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered aromatic heterocyclic radical having 1 or 2 nitrogen atoms as ring members.


R3c, R4c, Rk independently of each other are in particular selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C7-cycloalkyl which is unsubstituted or partly or completely halogenated; C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4-alkyl, phenyl, benzyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2 or 3 heteroatoms as ring members which are selected from the group consisting of O, N and S, where phenyl, benzyl and heterocyclyl are unsubstituted or substituted by 1, 2 or 3 groups which are identical or different and selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl and C1-C4-alkoxy.


More preferably R3c, R4c, Rk independently of each other are selected from the group consisting of hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1, 2 or 3 heteroatoms as ring members which are selected from the group consisting of O, N and S.


In particular, R3c, R4c, Rk independently of each other are selected from the group consisting of hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C3-C6-cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered aromatic heterocyclic radical having 1 or 2 nitrogen atoms as ring members.


R3d, R4d independently of each other are in particular selected from the group consisting of C1-C6-alkyl, C3-C7-cycloalkyl which is unsubstituted or partly or completely halogenated; C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4-alkyl, phenyl and benzyl.


More preferably R3d, R4d independently of each other are selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C1-C4-alkoxy-C1-C4-alkyl and C3-C7-cycloalkyl which is unsubstituted or partly or completely halogenated, and in particular selected from the group consisting of C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C3-C6-cycloalkyl.


R3e, R3f, R4e, R4f independently of each other are in particular selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C7-cycloalkyl which is unsubstituted or partially or completely halogenated; C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C1-C4-alkoxy-C1-C4-alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1, 2 or 3 groups which are identical or different and selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl and C1-C4-alkoxy, or R3e and R3f, together with the nitrogen atom to which they are bound, may form a 5-, 6 or 7-membered, saturated or unsaturated heterocyclic radical which may contain as a ring member a further heteroatom selected from the group consisting of O, S and N and which is unsubstituted or may carry 1, 2, 3 or 4 groups which are identical or different and selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl and C1-C4-alkoxy.


More preferably R3e, R3f, R4e, R4f independently of each other are selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl and benzyl, or R3e and R3f, together with the nitrogen atom to which they are bound, may form a 5- or 6-membered, saturated or unsaturated heterocyclic radical which may contain as a ring member a further heteroatom selected from the group consisting of O, S and N and which is unsubstituted or may carry 1, 2 or 3 groups which are identical or different and selected from the group consisting of halogen, C1-C4-alkyl and C1-C4-haloalkyl.


In particular, R3e, R3f, R4e, R4f independently of each other are selected from the group consisting of hydrogen and C1-C4-alkyl, or R3e and R3f, together with the nitrogen atom to which they are bound, may form a 5- or 6-membered, saturated heterocyclic radical which may contain as a ring member a further heteroatom selected from the group consisting of O, S and N and which is unsubstituted or may carry 1, 2 or 3 methyl groups.


R3g, R4g independently of each other are in particular selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C7-cycloalkyl which is unsubstituted or partly or completely halogenated; C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4-alkyl, phenyl and benzyl.


More preferably R3g, R4g independently of each other are in particular selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, benzyl, C1-C4-alkoxy-C1-C4-alkyl and C3-C7-cycloalkyl which is unsubstituted or partly or completely halogenated, and in particular selected from the group consisting of hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, benzyl and C3-C6-cycloalkyl.


R3h, R4h independently of each other are in particular selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C7-cycloalkyl which is unsubstituted or partly or completely halogenated; C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4-alkyl, phenyl, benzyl and a radical C(═O)—Rk, where Rk is H, C1-C4-alkyl, C1-C4-haloalkyl or phenyl.


More preferably R3h, R4h independently of each other are selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, benzyl, C1-C4-alkoxy-C1-C4-alkyl and C3-C7-cycloalkyl which is unsubstituted or partly or completely halogenated, and in particular selected from hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, benzyl and C3-C6-cycloalkyl; or


R3g and R3h or R4g and R4h, together with the nitrogen atom to which they are bound, may in particular also form a 5-, 6 or 7-membered, saturated or unsaturated heterocyclic radical which may contain as a ring member a further heteroatom selected from the group consisting of O, S and N and which is unsubstituted or may carry 1, 2, 3 or 4 groups which are identical or different and selected from the group consisting of ═O, halogen, C1-C4-alkyl and C1-C4-haloalkyl and C1-C4-alkoxy; more preferably R3g and R3h or R4g and R4h, together with the nitrogen atom to which they are bound, may form a 5- or 6-membered, saturated or unsaturated heterocyclic radical, which may contain as a ring member a further heteroatom selected from the group consisting of O, S and N and which is unsubstituted or may carry 1, 2 or 3 groups which are identical or different and selected from the group consisting of halogen, C1-C4-alkyl and C1-C4-haloalkyl; and in particular, R3g and R3h or R4g and R4h, together with the nitrogen atom to which they are bound, may form a 5- or 6-membered, saturated heterocyclic radical which may contain as a ring member a further heteroatom selected from the group consisting of O, S and N and which is unsubstituted or may carry 1, 2 or 3 methyl groups.


Rz is selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C3-C7-cycloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, phenyl, benzyl, heterocyclyl and heterocyclylmethyl, where heterocyclyl in the last two mentioned radicals is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1, 2 or 3 heteroatoms as ring members which are selected from the group consisting of O, N and S, where phenyl, benzyl and heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4 groups which are identical or different and selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy.


Preferably, Rz is selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1, 2, 3 or 4 groups which are identical or different and selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy.


More preferably, Rz is selected from the group consisting of C1-C4-alkyl, C1-C3-haloalkyl, C1-C4-alkoxy, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 or 2 groups which are identical or different and selected from halogen, C1-C4-alkyl and C1-C4-haloalkyl; and in particular Rz is C1-C3-alkyl, C1-C3-haloalkyl or C1-C4-alkoxy.


Irrespectively of its occurrence, the variable n is in particular 0 or 2.


Irrespectively of its occurrence, the variable k is in particular 0 or 2, and especially 2.


Particularly preferred are compounds of formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′, their N-oxides and their salts, wherein the combination of the variables R1 and R3 have the following meanings:

  • R1 is selected from the group consisting of halogen, nitro, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio, C1-C4-haloalkylthio and C1-C4-alkylsulfonyl, in particular from the group consisting of F, Cl, Br, I, nitro, CH3, CF3, OCH3, SCH3, SCF3, SO2CH3 and CH2OCH2CH2OCH3, more specifically from the group consisting of F, Cl, Br, I, nitro, CH3, CF3, OCH3, SCH3 and SO2CH3, even more specifically from the group consisting of Cl, Br, CH3, CF3 and OCH3, particularly from Cl, CH3 and OCH3, and especially R1 is Cl or CH3; and
  • R3 is selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkyl-S(O), C1-C4-haloalkyl-S(O), C1-C4-alkyl-S(O)2, and C1-C4-haloalkyl-S(O)2, more particularly from the group consisting of halogen, C1-C2-alkyl, C1-C2-haloalkyl, C1-C2-haloalkoxy, C1-C2-alkylthio, C1-C2-haloalkylthio, C1-C2-alkyl-S(O), C1-C2-haloalkyl-S(O), C1-C2-alkyl-S(O)2 and C1-C2-haloalkyl-S(O)2, especially from the group consisting of Cl, F, Br, I, CH3, CF3, CHF2, OCF3, OCHF2, SCH3, SCF3, SCHF2, S(O)CH3, S(O)CH2CH3, S(O)2CH3 and S(O)2CH2CH3, and more specifically R3 is C, Br, CF3, SCH3, S(O)CH3 or S(O)2CH3.


Specifically, in compounds of formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′, the combination of the variables R1 and R3 have the following meanings:

  • R1 is selected from the group consisting of Cl, CH3 and OCH3, and especially from Cl or CH3; and
  • R3 is halogen; specifically Cl or Br.


A particular preferred group 1 of compounds of the invention are compounds of formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′, their N-oxides and their salts, wherein the combination of variables R4 and R5 have the following meanings:


R4 is hydrogen, chlorine or fluorine; and in particular is hydrogen;


R5 is different from hydrogen and in particular selected from the group consisting of halogen, CHF2 and CF3; and in particular from chlorine and fluorine and is specifically fluorine.


A further particular preferred group 2 of compounds of the invention are compounds of formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′, their N-oxides and their salts, wherein the combination of variables R4 and R5 have the following meanings:


R4 is chlorine or fluorine;


R5 is hydrogen.


A further particular preferred group 3 of compounds of the invention are compounds of formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′, their N-oxides and their salts, wherein both variables R4 and R5 are hydrogen.


Amongst the compounds of groups 1, 2 and 3, preference is given to those, where Q is Q1 or Q2 or Q4, and is specifically Q1.


Amongst the compounds of groups 1, 2 and 3, preference is given to those, where Z2 is a covalent bond.


Amongst the compounds of groups 1, 2 and 3, particular preference is given to those, where Q is Q1 or Q2 or Q4, specifically Q1, and Z2 is a covalent bond.


Amongst the compounds of groups 1, 2 and 3, preference is given to those, where Q is Q1 or Q2 or Q4, specifically Q1, Z2 is a covalent bond and where the combination of R1 and R3 is as follows:

  • R1 is selected from the group consisting of halogen, nitro, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio, C1-C4-haloalkylthio and C1-C4-alkylsulfonyl, in particular from the group consisting of F, Cl, Br, I, nitro, CH3, CF3, OCH3, SCH3, SCF3, SO2CH3 and CH2OCH2CH2OCH3, more specifically from the group consisting of F, Cl, Br, I, nitro, CH3, CF3, OCH3, SCH3 and SO2CH3, even more specifically from the group consisting of Cl, Br, CH3, CF3 and OCH3, particularly from Cl, CH3 and OCH3, and especially R1 is Cl or CH3; and
  • R3 is selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkyl-S(O), C1-C4-haloalkyl-S(O), C1-C4-alkyl-S(O)2, and C1-C4-haloalkyl-S(O)2, more particularly from the group consisting of halogen, C1-C2-alkyl, C1-C2-haloalkyl, C1-C2-haloalkoxy, C1-C2-alkylthio, C1-C2-haloalkylthio, C1-C2-alkyl-S(O), C1-C2-haloalkyl-S(O), C1-C2-alkyl-S(O)2 and C1-C2-haloalkyl-S(O)2, especially from the group consisting of Cl, F, Br, I, CH3, CF3, CHF2, OCF3, OCHF2, SCH3, SCF3, SCHF2, S(O)CH3, S(O)CH2CH3, S(O)2CH3 and S(O)2CH2CH3, and more specifically R3 is Cl, Br, CF3, SCH3, S(O)CH3 or S(O)2CH3.


Amongst the compounds of groups 1, 2 and 3, more preference is given to those, where Q is Q1 or Q2 or Q4, specifically Q1, Z2 is a covalent bond and where the combination of R1 and

  • R3 is as follows:
  • R1 is selected from the group consisting of Cl, CH3 and OCH3, and especially from C or CH3; and
  • R3 is halogen; specifically Cl or Br.


A particular preferred group 1a of compounds of the invention are compounds of formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′, their N-oxides and their salts, wherein the variables R1, R3, R4, R6a, R6b, R6c, R6d and R7 have the following meanings:

  • R1 is selected from the group consisting of halogen, nitro, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio, C1-C4-haloalkylthio and C1-C4-alkylsulfonyl, in particular from the group consisting of F, Cl, Br, I, nitro, CH3, CF3, OCH3, SCH3, SCF3, SO2CH3 and CH2OCH2CH2OCH3, more specifically from the group consisting of F, Cl, Br, I, nitro, CH3, CF3, OCH3, SCH3 and SO2CH3, even more specifically from the group consisting of Cl, Br, CH3, CF3 and OCH3, particularly from Cl, CH3 and OCH3, and especially R1 is Cl or CH3;
  • R3 is selected from halogen, nitro, C1-C2-alkyl, C1-C2-haloalkyl, C1-C2-haloalkoxy, C1-C2-alkylthio, C1-C2-haloalkylthio, C1-C2-alkyl-S(O), C1-C2-haloalkyl-S(O), C1-C2-alkyl-S(O)2 and C1-C2-haloalkyl-S(O)2 and where R3 is in particular selected from the group consisting of Cl, Br, CF3, SCH3, S(O)CH3 and S(O)2CH3;
  • R4 is hydrogen, chlorine or fluorine; and in particular is hydrogen;
  • R5 is selected from the group consisting of halogen, CHF2 and CF3; and in particular from chlorine and fluorine;
  • R6a, R6b, R6c, Rd are, independently of each other, selected from CH3, CH3CH2, CH3OCH2CH2 and CH3OCH2; and in particular from CH3 and CH3CH2; and
  • R7 is hydrogen.


Another particular preferred group 2a of compounds of the invention are compounds of formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′, their N-oxides and their salts, wherein wherein Q is Q1, Q2, Q3 or Q4 and the variables R1, R3, R4, R6a, R6b, R6c, R6d and R7 have the following meanings:

  • R1 is selected from the group consisting of halogen, nitro, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio, C1-C4-haloalkylthio and C1-C4-alkylsulfonyl, in particular from the group consisting of F, Cl, Br, I, nitro, CH3, CF3, OCH3, SCH3, SCF3, SO2CH3 and CH2OCH2CH2OCH3, more specifically from the group consisting of F, Cl, Br, I, nitro, CH3, CF3, OCH3, SCH3 and SO2CH3, even more specifically from the group consisting of Cl, Br, CH3, CF3 and OCH3, particularly from Cl, CH3 and OCH3, and especially R1 is Cl or CH3;
  • R3 is selected from halogen, nitro, C1-C2-alkyl, C1-C2-haloalkyl, C1-C2-haloalkoxy, C1-C2-alkylthio, C1-C2-haloalkylthio, C1-C2-alkyl-S(O), C1-C2-haloalkyl-S(O), C1-C2-alkyl-S(O)2 and C1-C2-haloalkyl-S(O)2 and where R3 is in particular selected from the group consisting of Cl, Br, CF3, SCH3, S(O)CH3 and S(O)2CH3;
  • R4 is chlorine or fluorine;
  • R5 is hydrogen;
  • R6a, R6b, R6c, R6d are, independently of each other, selected from CH3, CH3CH2, CH3OCH2CH2 and CH3OCH2; and in particular from CH3 and CH3CH2; and
  • R7 is hydrogen.


A further particular preferred group 3a of compounds of the invention are compounds of formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′, their N-oxides and their salts, wherein wherein Q is Q1, Q2, Q3 or Q4 and the variables R1, R3, R4, R6a, R6b, R6c, R6d and R7 have the following meanings:

  • R1 is selected from the group consisting of halogen, nitro, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio, C1-C4-haloalkylthio and C1-C4-alkylsulfonyl, in particular from the group consisting of F, Cl, Br, I, nitro, CH3, CF3, OCH3, SCH3, SCF3, SO2CH3 and CH2OCH2CH2OCH3, more specifically from the group consisting of F, Cl, Br, I, nitro, CH3, CF3, OCH3, SCH3 and SO2CH3, even more specifically from the group consisting of Cl, Br, CH3, CF3 and OCH3, particularly from Cl, CH3 and OCH3, and especially R1 is Cl or CH3;
  • R3 is selected from halogen, nitro, C1-C2-alkyl, C1-C2-haloalkyl, C1-C2-haloalkoxy, C1-C2-alkylthio, C1-C2-haloalkylthio, C1-C2-alkyl-S(O), C1-C2-haloalkyl-S(O), C1-C2-alkyl-S(O)2 and C1-C2-haloalkyl-S(O)2 and where R3 is in particular selected from the group consisting of Cl, Br, CF3, SCH3, S(O)CH3 and S(O)2CH3;
  • R4 is hydrogen;
  • R5 is hydrogen;
  • R6a, R6b, R6c, R6d are, independently of each other, selected from CH3, CH3CH2, CH3OCH2CH2 and CH3OCH2; and in particular from CH3 and CH3CH2; and
  • R7 is hydrogen.


Amongst the compounds of groups 1a, 2a and 3a, preference is given to those, where Q is Q1 or Q2 or Q4, and is specifically or Q1.


Amongst the compounds of groups 1a, 2a and 3a, preference is given to those, where Z2 is a covalent bond.


Amongst the compounds of groups 1a, 2a and 3a, particular preference is given to those, where Q is Q1 or Q2 or Q4, specifically Q1, and Z2 is a covalent bond.


A an even more preferred group 1b of compounds of the invention are compounds of formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′, their N-oxides and their salts, wherein the variables R1, R2a, R2b, R2c, R3, R4, R6a, R6b, R6c, R6d and R7 have the following meanings:

  • R1 is selected from the group consisting of halogen, nitro, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio, C1-C4-haloalkylthio and C1-C4-alkylsulfonyl, in particular from the group consisting of F, Cl, Br, I, nitro, CH3, CF3, OCH3, SCH3, SCF3, SO2CH3 and CH2OCH2CH2OCH3, more specifically from the group consisting of F, Cl, Br, I, nitro, CH3, CF3, OCH3, SCH3 and SO2CH3, even more specifically from the group consisting of Cl, Br, CH3, CF3 and OCH3, particularly from Cl, CH3 and OCH3, and especially R1 is Cl or CH3;
  • R2a is selected from the group consisting of C1-C4-alkyl, C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkyl-methyl, fluorinated C1-C4-alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1, 2, 3 or 4 radicals R21 which are identical or different and where R21 is preferably selected from the group consisting of halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy and where R21 is in particular selected from the group consisting of halogen, C1-C4-alkyl, fluorinated C1-C2-alkyl, C1-C4-alkoxy and fluorinated C1-C2-alkoxy and especially from the group consisting of halogen, methyl and methoxy; hydrogen, C1-C4-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-methyl and fluorinated C1-C4-alkyl,
    • R2a is more particularly selected from the group consisting of C1-C4-alkyl, C3-C7-cycloalkyl, fluorinated C1-C4-alkyl, C1-C4-alkoxy and phenyl, where phenyl is unsubstituted or substituted by 1 or 2 groups R21 which are identical or different and which are preferably selected from the group consisting of halogen, C1-C4-alkyl, fluorinated C1-C2-alkyl, C1-C4-alkoxy and fluorinated C1-C2-alkoxy and especially from the group consisting of halogen, methyl and methoxy,
    • R2a is even more particularly selected from the group consisting of C1-C4-alkyl, fluorinated C1-C2-alkyl, C3-C4-cycloalkyl, and phenyl which is unsubstituted or substituted by 1, 2 or 3 radicals R21 selected from the group consisting of halogen, C1-C4-alkyl, fluorinated C1-C2-alkyl, C1-C4-alkoxy and fluorinated C1-C2-alkoxy and where phenyl is in particular unsubstituted or substituted by 1, 2 or 3 radicals selected from the group consisting of halogen, methyl and methoxy,
    • R2a is especially selected from the group consisting of methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2—, CF3CH2—, CH3O—, 4-Cl-phenyl, 4-methoxyphenyl, 4-methylphenyl and 2,6-dimethylphenyl;
  • R2b is selected from the group consisting of hydrogen, C1-C4-alkyl, C3-C7-cycloalkyl and fluorinated C1-C4-alkyl, in particular selected from the group consisting of hydrogen, C1-C4-alkyl, fluorinated C1-C2-alkyl and C3-C4-cycloalkyl and especially selected from the group consisting of hydrogen, methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2— and CF3CH2—;
  • or
  • R2a and R2b, together with the nitrogen atom to which they are bound, may form a 5- or 6-membered, saturated or unsaturated heterocyclic radical which may contain as a ring member a further heteroatom selected from the group consisting of O, S and N and which is unsubstituted or may carry 1, 2, 3 or 4 groups R2d which are identical or different and in particular selected from the group consisting of ═O, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy, and where R2a and R2b, together with the nitrogen atom to which they are bound, in particular form 4-morpholinyl, 4-thiomorpholinyl, 1-piperidinyl and 1-pyrrolidinyl, where 4-morpholinyl, 4-thiomorpholinyl, 1-piperidinyl and 1-pyrrolidinyl are unsubstituted or carry 1, 2, 3 or 4 groups R2d which are selected from the group consisting of C1-C4-alkyl and fluorinated C1-C4-alkyl, preferably from methyl, ethyl and trifluoromethyl;
  • R2c is hydrogen or C1-C4-alkyl and especially hydrogen;
  • R3 is selected from halogen, nitro, C1-C2-alkyl, C1-C2-haloalkyl, C1-C2-haloalkoxy, C1-C2-alkylthio, C1-C2-haloalkylthio, C1-C2-alkyl-S(O), C1-C2-haloalkyl-S(O), C1-C2-alkyl-S(O)2 and C1-C2-haloalkyl-S(O)2 and where R3 is in particular selected from the group consisting of Cl, Br, CF3, SCH3, S(O)CH3 and S(O)2CH3; and where R3 is specifically Cl or Br;
  • R4 is hydrogen, chlorine or fluorine; and in particular is hydrogen;
  • R5 is selected from the group consisting of halogen, CHF2 and CF3; and in particular from chlorine and fluorine;
  • R6a, R6b, R6c, R6d are, independently of each other, selected from CH3, CH3CH2, CH3OCH2CH2 and CH3OCH2; and in particular from CH3 and CH3CH2; and
  • R7 is hydrogen.


A likewise more preferred group 2b of compounds of the invention are compounds of formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′, their N-oxides and their salts, wherein the variables R1, R2a, R2b, R2c, R3, R4, R6a, R6b, R6c, R6d and R7 have the following meanings:

  • R1 is selected from the group consisting of halogen, nitro, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio, C1-C4-haloalkylthio and C1-C4-alkylsulfonyl, in particular from the group consisting of F, Cl, Br, I, nitro, CH3, CF3, OCH3, SCH3, SCF3, SO2CH3 and CH2OCH2CH2OCH3, more specifically from the group consisting of F, Cl, Br, I, nitro, CH3, CF3, OCH3, SCH3 and SO2CH3, even more specifically from the group consisting of Cl, Br, CH3, CF3 and OCH3, particularly from Cl, CH3 and OCH3, and especially R1 is Cl or CH3;
  • R2a is selected from the group consisting of C1-C4-alkyl, C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkyl-methyl, fluorinated C1-C4-alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1, 2, 3 or 4 radicals R21 which are identical or different and where R21 is preferably selected from the group consisting of halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy and where R21 is in particular selected from the group consisting of halogen, C1-C4-alkyl, fluorinated C1-C2-alkyl, C1-C4-alkoxy and fluorinated C1-C2-alkoxy and especially from the group consisting of halogen, methyl and methoxy; hydrogen, C1-C4-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-methyl and fluorinated C1-C4-alkyl,
    • R2a is more particularly selected from the group consisting of C1-C4-alkyl, C3-C7-cycloalkyl, fluorinated C1-C4-alkyl, C1-C4-alkoxy and phenyl, where phenyl is unsubstituted or substituted by 1 or 2 groups R21 which are identical or different and which are preferably selected from the group consisting of halogen, C1-C4-alkyl, fluorinated C1-C2-alkyl, C1-C4-alkoxy and fluorinated C1-C2-alkoxy and especially from the group consisting of halogen, methyl and methoxy,
    • R2a is even more particularly selected from the group consisting of C1-C4-alkyl, fluorinated C1-C2-alkyl, C3-C4-cycloalkyl, and phenyl which is unsubstituted or substituted by 1, 2 or 3 radicals R21 selected from the group consisting of halogen, C1-C4-alkyl, fluorinated C1-C2-alkyl, C1-C4-alkoxy and fluorinated C1-C2-alkoxy and where phenyl is in particular unsubstituted or substituted by 1, 2 or 3 radicals selected from the group consisting of halogen, methyl and methoxy,
    • R2a is especially selected from the group consisting of methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2—, CF3CH2—, CH3O—, 4-Cl-phenyl, 4-methoxyphenyl, 4-methylphenyl and 2,6-dimethylphenyl;
  • R2b is selected from the group consisting of hydrogen, C1-C4-alkyl, C3-C7-cycloalkyl and fluorinated C1-C4-alkyl, in particular selected from the group consisting of hydrogen, C1-C4-alkyl, fluorinated C1-C2-alkyl and C3-C4-cycloalkyl and especially selected from the group consisting of hydrogen, methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2— and CF3CH2—;
  • or
  • R2a and R2b, together with the nitrogen atom to which they are bound, may form a 5- or 6-membered, saturated or unsaturated heterocyclic radical which may contain as a ring member a further heteroatom selected from the group consisting of O, S and N and which is unsubstituted or may carry 1, 2, 3 or 4 groups R2d which are identical or different and in particular selected from the group consisting of ═O, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy, and where R2a and R2b, together with the nitrogen atom to which they are bound, in particular form 4-morpholinyl, 4-thiomorpholinyl, 1-piperidinyl and 1-pyrrolidinyl, where 4-morpholinyl, 4-thiomorpholinyl, 1-piperidinyl and 1-pyrrolidinyl are unsubstituted or carry 1, 2, 3 or 4 groups R2d which are selected from the group consisting of C1-C4-alkyl and fluorinated C1-C4-alkyl, preferably from methyl, ethyl and trifluoromethyl;
  • R2c is hydrogen or C1-C4-alkyl and especially hydrogen;
  • R3 is selected from halogen, nitro, C1-C2-alkyl, C1-C2-haloalkyl, C1-C2-haloalkoxy, C1-C2-alkylthio, C1-C2-haloalkylthio, C1-C2-alkyl-S(O), C1-C2-haloalkyl-S(O), C1-C2-alkyl-S(O)2 and C1-C2-haloalkyl-S(O)2 and where R3 is in particular selected from the group consisting of Cl, Br, CF3, SCH3, S(O)CH3 and S(O)2CH3; and where R3 is specifically Cl or Br;
  • R4 is chlorine or fluorine;
  • R5 is hydrogen;
  • R6a, R6b, R6c, R6d are, independently of each other, selected from CH3, CH3CH2, CH3OCH2CH2 and CH3OCH2; and in particular from CH3 and CH3CH2; and
  • R7 is hydrogen.


A likewise more preferred group 3b of compounds of the invention are compounds of formulae I, I.A, I.B, I.C, I.D, I′, I.A′, I.B′, I.C′ and I.D′, their N-oxides and their salts, wherein the variables R1, R2a, R2b, R2c, R3, R4, R6a, R6b, R6c, R6d and R7 have the following meanings:

  • R1 is selected from the group consisting of halogen, nitro, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio, C1-C4-haloalkylthio and C1-C4-alkylsulfonyl, in particular from the group consisting of F, Cl, Br, I, nitro, CH3, CF3, OCH3, SCH3, SCF3, SO2CH3 and CH2OCH2CH2OCH3, more specifically from the group consisting of F, Cl, Br, I, nitro, CH3, CF3, OCH3, SCH3 and SO2CH3, even more specifically from the group consisting of Cl, Br, CH3, CF3 and OCH3, particularly from Cl, CH3 and OCH3, and especially R1 is Cl or CH3;
  • R2a is selected from the group consisting of C1-C4-alkyl, C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkyl-methyl, fluorinated C1-C4-alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1, 2, 3 or 4 radicals R21 which are identical or different and where R21 is preferably selected from the group consisting of halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy and where R21 is in particular selected from the group consisting of halogen, C1-C4-alkyl, fluorinated C1-C2-alkyl, C1-C4-alkoxy and fluorinated C1-C2-alkoxy and especially from the group consisting of halogen, methyl and methoxy; hydrogen, C1-C4-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-methyl and fluorinated C1-C4-alkyl,
    • R2a is more particularly selected from the group consisting of C1-C4-alkyl, C3-C7-cycloalkyl, fluorinated C1-C4-alkyl, C1-C4-alkoxy and phenyl, where phenyl is unsubstituted or substituted by 1 or 2 groups R21 which are identical or different and which are preferably selected from the group consisting of halogen, C1-C4-alkyl, fluorinated C1-C2-alkyl, C1-C4-alkoxy and fluorinated C1-C2-alkoxy and especially from the group consisting of halogen, methyl and methoxy,
    • R2a is even more particularly selected from the group consisting of C1-C4-alkyl, fluorinated C1-C2-alkyl, C3-C4-cycloalkyl, and phenyl which is unsubstituted or substituted by 1, 2 or 3 radicals R21 selected from the group consisting of halogen, C1-C4-alkyl, fluorinated C1-C2-alkyl, C1-C4-alkoxy and fluorinated C1-C2-alkoxy and where phenyl is in particular unsubstituted or substituted by 1, 2 or 3 radicals selected from the group consisting of halogen, methyl and methoxy,
    • R2a is especially selected from the group consisting of methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2—, CF3CH2—, CH3O—, 4-Cl-phenyl, 4-methoxyphenyl, 4-methylphenyl and 2,6-dimethylphenyl;
  • R2b is selected from the group consisting of hydrogen, C1-C4-alkyl, C3-C7-cycloalkyl and fluorinated C1-C4-alkyl, in particular selected from the group consisting of hydrogen, C1-C4-alkyl, fluorinated C1-C2-alkyl and C3-C4-cycloalkyl and especially selected from the group consisting of hydrogen, methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2— and CF3CH2—;
  • or
  • R2a and R2b, together with the nitrogen atom to which they are bound, may form a 5- or 6-membered, saturated or unsaturated heterocyclic radical which may contain as a ring member a further heteroatom selected from the group consisting of O, S and N and which is unsubstituted or may carry 1, 2, 3 or 4 groups R2d which are identical or different and in particular selected from the group consisting of ═O, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy, and where R2a and R2b, together with the nitrogen atom to which they are bound, in particular form 4-morpholinyl, 4-thiomorpholinyl, 1-piperidinyl and 1-pyrrolidinyl, where 4-morpholinyl, 4-thiomorpholinyl, 1-piperidinyl and 1-pyrrolidinyl are unsubstituted or carry 1, 2, 3 or 4 groups R2d which are selected from the group consisting of C1-C4-alkyl and fluorinated C1-C4-alkyl, preferably from methyl, ethyl and trifluoromethyl;
  • R2c is hydrogen or C1-C4-alkyl and especially hydrogen.
  • R3 is selected from halogen, nitro, C1-C2-alkyl, C1-C2-haloalkyl, C1-C2-haloalkoxy, C1-C2-alkylthio, C1-C2-haloalkylthio, C1-C2-alkyl-S(O), C1-C2-haloalkyl-S(O), C1-C2-alkyl-S(O)2 and C1-C2-haloalkyl-S(O)2 and where R3 is in particular selected from the group consisting of Cl, Br, CF3, SCH3, S(O)CH3 and S(O)2CH3; and where R3 is specifically Cl or Br;
  • R4 is hydrogen;
  • R5 is hydrogen;
  • R6a, R6b, R6c, R6d are, independently of each other, selected from CH3, CH3CH2, CH3OCH2CH2 and CH3OCH2; and in particular from CH3 and CH3CH2; and
  • R7 is hydrogen.


Amongst the compounds of groups 1b, 2b and 3b, preference is given to those, where Q is Q1 or Q2 or Q4, and is specifically Q1.


Amongst the compounds of groups 1b, 2b and 3b, preference is given to those, where Z2 is a covalent bond.


Amongst the compounds of groups 1b, 2b and 3b, particular preference is given to those, where Q is Q1 or Q2 or Q4, and is specifically Q1, and Z2 is a covalent bond.


Amongst the compounds of groups 1b, 2b and 3b, particular preference is given to those, where Q is Q1 or Q2 or Q4, and is specifically Q1, and Z2 is a covalent bond.


A very preferred group 1c of compounds of the invention are compounds of formulae I.A′, I.B′ and I.D′, their N-oxides and their salts, wherein the variables R1, R2a, R2b, R2c, R3, R4, R6a, R6b, R6c, R6d and R7 have the following meanings:

  • R1 is halogen, C1-C2-alkyl or C1-C2-alkoxy, such as Cl, CH3 or OCH3; in particular halogen or C1-C2-alkyl, specifically Cl or CH3;
  • R2a is selected from the group consisting of hydrogen, C1-C4-alkyl, C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkyl-methyl, fluorinated C1-C4-alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1, 2, 3 or 4 radicals selected from the group consisting of halogen, methyl and methoxy,
    • R2a is in particular selected from the group consisting of C1-C4-alkyl, C1-C4-alkoxy, C3-C7-cycloalkyl, fluorinated C1-C4-alkyl and phenyl, where phenyl is unsubstituted or substituted by 1, 2 or 3 radicals selected from the group consisting of halogen, methyl and methoxy, R2a is even more particularly selected from the group consisting of C1-C4-alkyl, fluorinated C1-C2-alkyl, C3-C4-cycloalkyl, and phenyl which is unsubstituted or substituted by 1, 2 or 3 radicals selected from the group consisting of halogen, methyl and methoxy, specifically by 1, 2 or 3 methyl groups; R2a is especially selected from the group consisting of methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2—, CF3CH2—, CH3O—, 4-Cl-phenyl, 4-methoxyphenyl, 4-methylphenyl and 2,6-dimethylphenyl;
  • R2b is selected from the group consisting of C1-C4-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-methyl and fluorinated C1-C4-alkyl; in particular selected from the group consisting of hydrogen, C1-C4-alkyl, fluorinated C1-C2-alkyl and C3-C4-cycloalkyl and especially selected from the group consisting of hydrogen, methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2— and CF3CH2—;
  • or
  • R2a and R2b, together with the nitrogen atom to which they are bound, form a 5- or 6-membered, saturated heterocyclic radical which may contain as a ring member a further heteroatom selected from the group consisting of O, S and N and where the heterocyclic radical is selected from the group consisting of 4-morpholinyl, 4-thiomorpholinyl, 1-piperidinyl and 1-pyrrolidinyl, where 4-morpholinyl, 4-thiomorpholinyl, 1-piperidinyl and 1-pyrrolidinyl are unsubstituted or carry 1, 2, 3 or 4 groups R2d which are selected from the group consisting of C1-C4-alkyl and fluorinated C1-C4-alkyl, where R2d is especially selected from the group consisting of methyl and trifluoromethyl;
  • R2c is selected from the group consisting of hydrogen and C1-C4-alkyl, especially hydrogen;
  • R3 is selected from the group consisting of halogen, C1-C2-alkyl, fluorinated C1-C2-alkyl, S—C1-C2-alkyl, S(O)—C1-C2-alkyl, S(O)2—C1-C2-alkyl, S-(fluorinated C1-C2-alkyl), S(O)-(fluorinated C1-C2-alkyl) and S(O)2-(fluorinated C1-C2-alkyl) and where R3 is in particular selected from the group consisting of Cl, Br, CF3, SCH3, S(O)CH3 and S(O)2CH3;
  • R4 is hydrogen;
  • R5 is fluorine;
  • R6a, R6b, independently of each other are selected from the group consisting of C1-C4-alkyl and C1-C4-alkoxy-C1-C4-alkyl;
  • R7 is as defined above and in particular hydrogen.


In a particular embodiment, in the compounds of formula I, I.A, I.B., I.C, I.D, I′, I.A′, I.B′ and I.D′

  • R1 is halogen, C1-C2-alkyl or C1-C2-alkoxy, in particular Cl, CH3 or OCH3;
  • R2a is selected from the group consisting of C1-C4-alkyl, C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkyl-methyl, fluorinated C1-C4-alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1, 2, 3 or 4 radicals selected from the group consisting of halogen, methyl and methoxy;
  • R2b is selected from the group consisting of hydrogen, C1-C4-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-methyl and fluorinated C1-C4-alkyl; or
  • R2a and R2b, together with the nitrogen atom to which they are bound, form a 5- or 6-membered saturated heterocyclic radical which is selected from the group consisting of 4-morpholinyl, 4-thiomorpholinyl, 1-piperidinyl and 1-pyrrolidinyl, where 4-morpholinyl, 4-thiomorpholinyl, 1-piperidinyl and 1-pyrrolidinyl are unsubstituted or carry 1, 2, 3 or 4 groups R2d which are selected from the group consisting of C1-C4-alkyl and fluorinated C1-C4-alkyl;
  • R2c is selected from the group consisting of hydrogen and C1-C4-alkyl;
  • R3 is selected from the group consisting of halogen, C1-C2-alkyl, fluorinated C1-C2-alkyl, S—C1-C2-alkyl, S(O)—C1-C2-alkyl, S(O)2—C1-C2-alkyl, S-(fluorinated C1-C2-alkyl), S(O)-(fluorinated C1-C2-alkyl) and S(O)2-(fluorinated C1-C2-alkyl);
  • R4 is hydrogen,
  • R5 is hydrogen or fluorine;
  • R6a, R6b and R6d, independently of each other, are selected from the group consisting of C1-C4-alkyl and C1-C4-alkoxy-C1-C4-alkyl; and
  • R7 is hydrogen.


In such compounds, the compounds of formula I are in particular compounds of formulae I.A′, I.B′ or I.D′ (i.e. Z2 is a covalent bond) and specifically of formula I.A′.


In a more particular embodiment, in the compounds of formula I, I.A, I.B., I.C, I.D, I′, I.A′, I.B′ and I.D′

  • R1 is halogen, C1-C2-alkyl or C1-C2-alkoxy, in particular Cl, CH3 or OCH3;
  • R2a is selected from the group consisting of C1-C4-alkyl, C3-C6-cycloalkyl, fluorinated C1-C4-alkyl and phenyl which is unsubstituted or substituted by 1, 2, 3 or 4 methyl groups;
  • R2b is selected from the group consisting of hydrogen, C1-C4-alkyl and C3-C6-cycloalkyl; or
  • R2a and R2b, together with the nitrogen atom to which they are bound, form a 4-morpholinyl ring;
  • R2c is hydrogen;
  • R3 is halogen;
  • R4 is hydrogen,
  • R5 is hydrogen or fluorine;
  • R6a, R6b and R6d, independently of each other, are C1-C4-alkyl; and
  • R7 is hydrogen.


In such compounds, the compounds of formula I are in particular compounds of formulae I.A′, I.B′ or I.D′ (i.e. Z2 is a covalent bond) and specifically of formula I.A′.


In an even more particular embodiment, in the compounds of formula I, I.A, I.B., I.C, I.D, I′, I.A′, I.B′ and I.D′

  • R1 is halogen, C1-C2-alkyl or C1-C2-alkoxy, in particular Cl, CH3 or OCH3, specifically Cl or CH3;
  • R2a is selected from the group consisting of C1-C4-alkyl, C3-C4-cycloalkyl, fluorinated C1-C2-alkyl and phenyl which is unsubstituted or substituted by 1, 2 or 3 methyl groups;
  • R2b is selected from the group consisting of hydrogen, C1-C3-alkyl and C3-C4-cycloalkyl; or
  • R2a and R2b, together with the nitrogen atom to which they are bound, form a 4-morpholinyl ring;
  • R2c is hydrogen;
  • R3 is halogen;
  • R4 is hydrogen,
  • R5 is hydrogen or fluorine;
  • R6a, R6b and R6d, independently of each other, are C1-C2-alkyl; and
  • R7 is hydrogen.


In such compounds, the compounds of formula I are in particular compounds of formulae I.A′, I.B′ or I.D′ and specifically of formula I.A′.


Examples of preferred compounds are the individual compounds compiled in the following tables 1 to 48 below. Moreover, the meanings mentioned below 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.


Compounds I.A′.I, wherein Q is Q1, R4 is hydrogen, R5 is hydrogen, R6a is methyl, R7 is hydrogen, Z2 is a covalent bond and R2c is H:




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    • Table 1 Compounds of formula I.A′.I (I.A′.I.1-I.A′.I.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.A′.II, wherein Q is Q1, R4 is hydrogen, R5 is hydrogen, R6a is ethyl, R7 is hydrogen, Z2 is a covalent bond and R2c is H:




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    • Table 2 Compounds of formula I.A′.II (I.A′.II.1-I.A′.II.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.A′.III, wherein Q is Q1, R4 is hydrogen, R5 is hydrogen, R6a is methyl, R7 is hydrogen, Z2 is a covalent bond and R2c is methyl:




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    • Table 3 Compounds of formula I.A′.II (I.A′.III.1-I.A′.III.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.A′.IV, wherein Q is Q1, R4 is hydrogen, R5 is hydrogen, R6a is ethyl, R7 is hydrogen, Z2 is a covalent bond and R2c is methyl:




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    • Table 4 Compounds of formula I.A′.IV (I.A′.IV.1-I.A′.IV.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.A′.V, wherein Q is Q1, R4 is hydrogen, R5 is hydrogen, R6a is methyl, R7 is hydrogen, Z2 is a covalent bond and R2c is ethyl:




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    • Table 5 Compounds of formula I.A′.V (I.A′.V.1-I.A′.V.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.A′.VI, wherein Q is Q1, R4 is hydrogen, R5 is hydrogen, R6a is ethyl, R7 is hydrogen, Z2 is a covalent bond and R2c is ethyl:




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    • Table 6 Compounds of formula I.A′.VI (I.A′.VI.1-I.A′.VI.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.A′.VII, wherein Q is Q1, R4 is hydrogen, R5 is fluorine, R6a is methyl, R7 is hydrogen, Z2 is a covalent bond and R2c is H;




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    • Table 7 Compounds of formula I.A′.VI (I.A′.VII.1-I.A′.VII.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.A′.VIII, wherein Q is Q1, R4 is hydrogen, R5 is fluorine, R6a is ethyl, R7 is hydrogen, Z2 is a covalent bond and R2c is H:




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    • Table 8 Compounds of formula I.A′.VIII (I.A′.VIII.1-I.A′.VIII.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.A′.IX, wherein Q is Q1, R4 is hydrogen, R5 is fluorine, R6a is methyl, R7 is hydrogen, Z2 is a covalent bond and R2c is methyl:




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    • Table 9 Compounds of formula IA′.IX (I.A′.IX.1-I.A′.IX.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.A′.X, wherein Q is Q1, R4 is hydrogen, R5 is fluorine, R6a is ethyl, R7 is hydrogen, Z2 is a covalent bond and R2c is methyl:




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    • Table 10 Compounds of formula I.A′.X (I.A′.X.1-I.A′.X.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.A′.XI, wherein Q is Q1, R4 is hydrogen, R5 is fluorine, R6a is methyl, R7 is hydrogen, Z2 is a covalent bond and R2c is ethyl:




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    • Table 11 Compounds of formula I.A′.XI (I.A′.XI.1-I.A′.XI.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.A′.XII, wherein Q is Q1, R4 is hydrogen, R5 is fluorine, R6a is ethyl, R7 is hydrogen, Z2 is a covalent bond and R2c is ethyl:




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    • Table 12 Compounds of formula I.A′.XII (I.A′.XII.1-I.A′.XII.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.B′.I, wherein Q is Q2, R4 is hydrogen, R5 is hydrogen, R6b is methyl, R7 is hydrogen, Z2 is a covalent bond and R2c is H:




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    • Table 13 Compounds of formula I.B′.I (I.B′.I.1-I.B′.I.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.B′.II, wherein Q is Q2, R4 is hydrogen, R5 is hydrogen, R6b is ethyl, R7 is hydrogen, Z2 is a covalent bond and R2c is H:




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    • Table 14 Compounds of formula I.B′.II (I.B′.II.1-I.B′.II.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.B′.III, wherein Q is Q2, R4 is hydrogen, R5 is hydrogen, R6b is methyl, R7 is hydrogen, Z2 is a covalent bond and R2c is methyl:




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    • Table 15 Compounds of formula I.B′.II (I.B′.III.1-I.B′.III.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.B′.IV, wherein Q is Q2, R4 is hydrogen, R5 is hydrogen, R6b is ethyl, R7 is hydrogen, Z2 is a covalent bond and R2c is methyl:




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    • Table 16 Compounds of formula I.B′.IV (I.B′.IV.1-I.B′.IV.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.B′.V, wherein Q is Q2, R4 is hydrogen, R5 is hydrogen, R6b is methyl, R7 is hydrogen, Z2 is a covalent bond and R2c is ethyl:




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    • Table 17 Compounds of formula I.B′.V (I.B′.V.1-I.B′.V.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.B′.VI, wherein Q is Q2, R4 is hydrogen, R5 is hydrogen, R6b is ethyl, R7 is hydrogen, Z2 is a covalent bond and R2c is ethyl:




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    • Table 18 Compounds of formula I.B′.VI (I.B′.VI.1-I.B′.VI.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.B′.VII, wherein Q is Q2, R4 is hydrogen, R5 is fluorine, R6b is methyl, R7 is hydrogen, Z2 is a covalent bond and R2c is H:




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    • Table 19 Compounds of formula I.B′.VII (I.B′.VII.1-I.B′.VII.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.B′.VIII, wherein Q is Q2, R4 is hydrogen, R5 is fluorine, R6b is ethyl, R7 is hydrogen, Z2 is a covalent bond and R2c is H:




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    • Table 20 Compounds of formula I.B′.VIII (I.B′.VIII.1-I.B′.VIII.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.B′.IX, wherein Q is Q2, R4 is hydrogen, R5 is fluorine, R6b is methyl, R7 is hydrogen, Z2 is a covalent bond and R2c is methyl:




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    • Table 21 Compounds of formula I.B′.IX (I.B′.IX.1-I.B′.IX.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.B′.X, wherein Q is Q2, R4 is hydrogen, R5 is fluorine, R6b is ethyl, R7 is hydrogen, Z2 is a covalent bond and R2c is methyl:




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    • Table 22 Compounds of formula I.B′.X (I.B′.X.1-I.B′.X.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.B′.XI, wherein Q is Q2, R4 is hydrogen, R5 is fluorine, R6b is methyl, R7 is hydrogen, Z2 is a covalent bond and R2c is ethyl:




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    • Table 23 Compounds of formula I.B′.XI (I.B′.XI.1-I.B′.XI.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.B′.XII, wherein Q is Q2, R4 is hydrogen, R5 is fluorine, R6b is ethyl, R7 is hydrogen, Z2 is a covalent bond and R2c is ethyl:




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    • Table 24 Compounds of formula I.B′.XII (I.B′.XII.1-I.B′.XII.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.C′.I, wherein Q is Q3, R4 is hydrogen, R5 is hydrogen, R6c is methyl, R7 is hydrogen, Z2 is a covalent bond and R2c is H:




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    • Table 25 Compounds of formula I.C′.I (I.C′.I.1-I.C′.I.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.C′.II, wherein Q is Q3, R4 is hydrogen, R5 is hydrogen, R6c is ethyl, R7 is hydrogen, Z2 is a covalent bond and R2c is H:




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    • Table 26 Compounds of formula I.C′.II (I.C′.II.1-I.C′.II.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.C′.III, wherein Q is Q3, R4 is hydrogen, R5 is hydrogen, R6c is methyl, R7 is hydrogen, Z2 is a covalent bond and R2c is methyl:




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    • Table 27 Compounds of formula I.C′.III (I.C′.III.1-I.C′.III.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.C′.IV, wherein Q is Q3, R4 is hydrogen, R5 is hydrogen, R6c is ethyl, R7 is hydrogen, Z2 is a covalent bond and R2c is methyl:




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    • Table 28 Compounds of formula I.C′.IV (I.C′.IV.1-I.C′.IV.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.C′.V, wherein Q is Q3, R4 is hydrogen, R5 is hydrogen, R6c is methyl, R7 is hydrogen, Z2 is a covalent bond and R2c is ethyl:




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    • Table 29 Compounds of formula I.C′.V (I.C′.V.1-I.C′.V.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.C′.VI, wherein Q is Q3, R4 is hydrogen, R5 is hydrogen, R6c is ethyl, R7 is hydrogen, Z2 is a covalent bond and R2c is ethyl:




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    • Table 30 Compounds of formula I.C′.VI (I.C′.VI.1-I.C′.VI.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.C′.VII, wherein Q is Q3, R4 is hydrogen, R5 is fluorine, R6c is methyl, R7 is hydrogen, Z2 is a covalent bond and R2c is H:




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    • Table 31 Compounds of formula I.C′.VII (I.C′.VII.1-I.C′.VII.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.C′.VIII, wherein Q is Q3, R4 is hydrogen, R5 is fluorine, R6c is ethyl, R7 is hydrogen, Z2 is a covalent bond and R2c is H:




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    • Table 32 Compounds of formula I.C′.VII (I.C′.VIII.1-I.C′.VIII.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.C′.IX, wherein Q is Q3, R4 is hydrogen, R5 is fluorine, R6c is methyl, R7 is hydrogen, Z2 is a covalent bond and R2c is methyl:




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    • Table 33 Compounds of formula I.C′.IX (I.C′.IX.1-I.C′.IX.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.C′.X, wherein Q is Q3, R4 is hydrogen, R5 is fluorine, R6c is ethyl, R7 is hydrogen, Z2 is a covalent bond and R2c is methyl:




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    • Table 34 Compounds of formula I.C′.X (I.C′.X.1-I.C′.X.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.C′.XI, wherein Q is Q3, R4 is hydrogen, R5 is fluorine, R6c is methyl, R7 is hydrogen, Z2 is a covalent bond and R2c is ethyl:




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    • Table 35 Compounds of formula I.C′.XI (I.C′.XI.1-I.C′.XI.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.C′.XII, wherein Q is Q3, R4 is hydrogen, R5 is fluorine, R6c is ethyl, R7 is hydrogen, Z2 is a covalent bond and R2c is ethyl:




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    • Table 36 Compounds of formula I.C′.XII (I.C′.XII.1-I.C′.XII.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.D′.I, wherein Q is Q4, R4 is hydrogen, R5 is hydrogen, R6d is methyl, R7 is hydrogen, Z2 is a covalent bond and R2c is H:




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    • Table 37 Compounds of formula I.D′.I (I.D′.I.1-I.D′.I.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.D′.II, wherein Q is Q4, R4 is hydrogen, R5 is hydrogen, R6d is ethyl, R7 is hydrogen, Z2 is a covalent bond and R2c is H:




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    • Table 38 Compounds of formula I.D′.II (I.D′.II.1-I.D′.II.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.D′.Ill, wherein Q is Q4, R4 is hydrogen, R5 is hydrogen, R6d is methyl, R7 is hydrogen, Z2 is a covalent bond and R2c is methyl:




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    • Table 39 Compounds of formula I.D′.III (I.D′.III.1-I.D′.III.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.D′.IV, wherein Q is Q4, R4 is hydrogen, R5 is hydrogen, R6d is ethyl, R7 is hydrogen, Z2 is a covalent bond and R2c is methyl:




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    • Table 40 Compounds of formula I.D′.IV (I.D′.IV.1-I.D′.IV.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.D′.V, wherein Q is Q4, R4 is hydrogen, R5 is hydrogen, R6d is methyl, R7 is hydrogen, Z2 is a covalent bond and R2c is ethyl:




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    • Table 41 Compounds of formula I.D′.V (I.D′.V.1-I.D′.V.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.D′.VI, wherein Q is Q4, R4 is hydrogen, R5 is hydrogen, R6d is ethyl, R7 is hydrogen, Z2 is a covalent bond and R2c is ethyl:




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    • Table 42 Compounds of formula I.D′.VI (I.D′.VI.1-I.D′.VI.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.D′.VII, wherein Q is Q4, R4 is hydrogen, R5 is fluorine, R6d is methyl, R7 is hydrogen, Z2 is a covalent bond and R2c is H:




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    • Table 43 Compounds of formula I.D′.VII (I.D′.VII.1-I.D′.VII.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.D′.VIII, wherein Q is Q4, R4 is hydrogen, R5 is fluorine, R6d is ethyl, R7 is hydrogen, Z2 is a covalent bond and R2c is H:




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    • Table 44 Compounds of formula I.D′.VIII (I.D′.VIII.1-I.D′.VIII.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.D′.IX, wherein Q is Q4, R4 is hydrogen, R5 is fluorine, R6d is methyl, R7 is hydrogen, Z2 is a covalent bond and R2c is methyl:




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    • Table 45 Compounds of formula I.D′.IX (I.D′.IX.1-I.D′.IX.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.D′.X, wherein Q is Q4, R4 is hydrogen, R5 is fluorine, R6d is ethyl, R7 is hydrogen, Z2 is a covalent bond and R2c is methyl:




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    • Table 46 Compounds of formula I.D′.X (I.D′.X.1-I.D′.X.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.D′.XI, wherein Q is Q4, R4 is hydrogen, R5 is fluorine, R6d is methyl, R7 is hydrogen, Z2 is a covalent bond and R2c is ethyl:




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    • Table 47 Compounds of formula I.D′.XI (I.D′.XI.1-I.D′.XI.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A;





Compounds I.D′.XII, wherein Q is Q4, R4 is hydrogen, R5 is fluorine, R6d is ethyl, R7 is hydrogen, Z2 is a covalent bond and R2c is ethyl:




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    • Table 48 Compounds of formula I.D′.XII (I.D′.XII.1-I.D′.XII.1656) in which the combination of R1, R2a, R2b, and R3 for a compound corresponds in each case to one row of Table A.
















TABLE A






R1
R2a
R2b
R3







  1
Cl
CH3
H
Cl


  2
Cl
CH3
H
Br


  3
Cl
CH3
H
I


  4
Cl
CH3
H
CF3


  5
Cl
CH3
H
CH3S(O)


  6
Cl
CH3
H
CH3S(O)2


  7
Cl
C2H5
H
Cl


  8
Cl
C2H5
H
Br


  9
Cl
C2H5
H
I


 10
Cl
C2H5
H
CF3


 11
Cl
C2H5
H
CH3S(O)


 12
Cl
C2H5
H
CH3S(O)2


 13
Cl
CH3CH2CH2
H
Cl


 14
Cl
CH3CH2CH2
H
Br


 15
Cl
CH3CH2CH2
H
I


 16
Cl
CH3CH2CH2
H
CF3


 17
Cl
CH3CH2CH2
H
CH3S(O)


 18
Cl
CH3CH2CH2
H
CH3S(O)2


 19
Cl
(CH3)2CH
H
Cl


 20
Cl
(CH3)2CH
H
Br


 21
Cl
(CH3)2CH
H
I


 22
Cl
(CH3)2CH
H
CF3


 23
Cl
(CH3)2CH
H
CH3S(O)


 24
Cl
(CH3)2CH
H
CH3S(O)2


 25
Cl
(CH3)3C
H
Cl


 26
Cl
(CH3)3C
H
Br


 27
Cl
(CH3)3C
H
I


 28
Cl
(CH3)3C
H
CF3


 29
Cl
(CH3)3C
H
CH3S(O)


 30
Cl
(CH3)3C
H
CH3S(O)2


 31
Cl
c-C3H5
H
Cl


 32
Cl
c-C3H5
H
Br


 33
Cl
c-C3H5
H
I


 34
Cl
c-C3H5
H
CF3


 35
Cl
c-C3H5
H
CH3S(O)


 36
Cl
c-C3H5
H
CH3S(O)2


 37
Cl
CHF2CH2
H
Cl


 38
Cl
CHF2CH2
H
Br


 39
Cl
CHF2CH2
H
I


 40
Cl
CHF2CH2
H
CF3


 41
Cl
CHF2CH2
H
CH3S(O)


 42
Cl
CHF2CH2
H
CH3S(O)2


 43
Cl
CF3CH2
H
Cl


 44
Cl
CF3CH2
H
Br


 45
Cl
CF3CH2
H
I


 46
Cl
CF3CH2
H
CF3


 47
Cl
CF3CH2
H
CH3S(O)


 48
Cl
CF3CH2
H
CH3S(O)2


 49
Cl
CH3O
H
Cl


 50
Cl
CH3O
H
Br


 51
Cl
CH3O
H
I


 52
Cl
CH3O
H
CF3


 53
Cl
CH3O
H
CH3S(O)


 54
Cl
CH3O
H
CH3S(O)2


 55
Cl
C6H5
H
Cl


 56
Cl
C6H5
H
Br


 57
Cl
C6H5
H
I


 58
Cl
C6H5
H
CF3


 59
Cl
C6H5
H
CH3S(O)


 60
Cl
C6H5
H
CH3S(O)2


 61
Cl
4-Cl-C6H4
H
Cl


 62
Cl
4-Cl-C6H4
H
Br


 63
Cl
4-Cl-C6H4
H
I


 64
Cl
4-Cl-C6H4
H
CF3


 65
Cl
4-Cl-C6H4
H
CH3S(O)


 66
Cl
4-Cl-C6H4
H
CH3S(O)2


 67
Cl
4-CH3-C6H4
H
Cl


 68
Cl
4-CH3-C6H4
H
Br


 69
Cl
4-CH3-C6H4
H
I


 70
Cl
4-CH3-C6H4
H
CF3


 71
Cl
4-CH3-C6H4
H
CH3S(O)


 72
Cl
4-CH3-C6H4
H
CH3S(O)2


 73
Cl
4-CH3O-C6H4
H
Cl


 74
Cl
4-CH3O-C6H4
H
Br


 75
Cl
4-CH3O-C6H4
H
I


 76
Cl
4-CH3O-C6H4
H
CF3


 77
Cl
4-CH3O-C6H4
H
CH3S(O)


 78
Cl
4-CH3O-C6H4
H
CH3S(O)2


 79
Cl
2,6-(CH3)2-C6H3
H
Cl


 80
Cl
2,6-(CH3)2-C6H3
H
Br


 81
Cl
2,6-(CH3)2-C6H3
H
I


 82
Cl
2,6-(CH3)2-C6H3
H
CF3


 83
Cl
2,6-(CH3)2-C6H3
H
CH3S(O)


 84
Cl
2,6-(CH3)2-C6H3
H
CH3S(O)2


 85
Cl
CH3
CH3
Cl


 86
Cl
CH3
CH3
Br


 87
Cl
CH3
CH3
I


 88
Cl
CH3
CH3
CF3


 89
Cl
CH3
CH3
CH3S(O)


 90
Cl
CH3
CH3
CH3S(O)2


 91
Cl
C2H5
CH3
Cl


 92
Cl
C2H5
CH3
Br


 93
Cl
C2H5
CH3
I


 94
Cl
C2H5
CH3
CF3


 95
Cl
C2H5
CH3
CH3S(O)


 96
Cl
C2H5
CH3
CH3S(O)2


 97
Cl
CH3CH2CH2
CH3
Cl


 98
Cl
CH3CH2CH2
CH3
Br


 99
Cl
CH3CH2CH2
CH3
I


 100
Cl
CH3CH2CH2
CH3
CF3


 101
Cl
CH3CH2CH2
CH3
CH3S(O)


 102
Cl
CH3CH2CH2
CH3
CH3S(O)2


 103
Cl
(CH3)2CH
CH3
Cl


 104
Cl
(CH3)2CH
CH3
Br


 105
Cl
(CH3)2CH
CH3
I


 106
Cl
(CH3)2CH
CH3
CF3


 107
Cl
(CH3)2CH
CH3
CH3S(O)


 108
Cl
(CH3)2CH
CH3
CH3S(O)2


 109
Cl
(CH3)3C
CH3
Cl


 110
Cl
(CH3)3C
CH3
Br


 111
Cl
(CH3)3C
CH3
I


 112
Cl
(CH3)3C
CH3
CF3


 113
Cl
(CH3)3C
CH3
CH3S(O)


 114
Cl
(CH3)3C
CH3
CH3S(O)2


 115
Cl
c-C3H5
CH3
Cl


 116
Cl
c-C3H5
CH3
Br


 117
Cl
c-C3H5
CH3
I


 118
Cl
c-C3H5
CH3
CF3


 119
Cl
c-C3H5
CH3
CH3S(O)


 120
Cl
c-C3H5
CH3
CH3S(O)2


 121
Cl
CHF2CH2
CH3
Cl


 122
Cl
CHF2CH2
CH3
Br


 123
Cl
CHF2CH2
CH3
I


 124
Cl
CHF2CH2
CH3
CF3


 125
Cl
CHF2CH2
CH3
CH3S(O)


 126
Cl
CHF2CH2
CH3
CH3S(O)2


 127
Cl
CF3CH2
CH3
Cl


 128
Cl
CF3CH2
CH3
Br


 129
Cl
CF3CH2
CH3
I


 130
Cl
CF3CH2
CH3
CF3


 131
Cl
CF3CH2
CH3
CH3S(O)


 132
Cl
CF3CH2
CH3
CH3S(O)2


 133
Cl
CH3O
CH3
Cl


 134
Cl
CH3O
CH3
Br


 135
Cl
CH3O
CH3
I


 136
Cl
CH3O
CH3
CF3


 137
Cl
CH3O
CH3
CH3S(O)


 138
Cl
CH3O
CH3
CH3S(O)2


 139
Cl
C6H5
CH3
Cl


 140
Cl
C6H5
CH3
Br


 141
Cl
C6H5
CH3
I


 142
Cl
C6H5
CH3
CF3


 143
Cl
C6H5
CH3
CH3S(O)


 144
Cl
C6H5
CH3
CH3S(O)2


 145
Cl
4-Cl-C6H4
CH3
Cl


 146
Cl
4-Cl-C6H4
CH3
Br


 147
Cl
4-Cl-C6H4
CH3
I


 148
Cl
4-Cl-C6H4
CH3
CF3


 149
Cl
4-Cl-C6H4
CH3
CH3S(O)


 150
Cl
4-Cl-C6H4
CH3
CH3S(O)2


 151
Cl
4-CH3-C6H4
CH3
Cl


 152
Cl
4-CH3-C6H4
CH3
Br


 153
Cl
4-CH3-C6H4
CH3
I


 154
Cl
4-CH3-C6H4
CH3
CF3


 155
Cl
4-CH3-C6H4
CH3
CH3S(O)


 156
Cl
4-CH3-C6H4
CH3
CH3S(O)2


 157
Cl
4-CH3O-C6H4
CH3
Cl


 158
Cl
4-CH3O-C6H4
CH3
Br


 159
Cl
4-CH3O-C6H4
CH3
I


 160
Cl
4-CH3O-C6H4
CH3
CF3


 161
Cl
4-CH3O-C6H4
CH3
CH3S(O)


 162
Cl
4-CH3O-C6H4
CH3
CH3S(O)2


 163
Cl
2,6-(CH3)2-C6H3
CH3
Cl


 164
Cl
2,6-(CH3)2-C6H3
CH3
Br


 165
Cl
2,6-(CH3)2-C6H3
CH3
I


 166
Cl
2,6-(CH3)2-C6H3
CH3
CF3


 167
Cl
2,6-(CH3)2-C6H3
CH3
CH3S(O)


 168
Cl
2,6-(CH3)2-C6H3
CH3
CH3S(O)2


 169
Cl
C2H5
C2H5
Cl


 170
Cl
C2H5
C2H5
Br


 171
Cl
C2H5
C2H5
I


 172
Cl
C2H5
C2H5
CF3


 173
Cl
C2H5
C2H5
CH3S(O)


 174
Cl
C2H5
C2H5
CH3S(O)2


 175
Cl
CH3CH2CH2
C2H5
Cl


 176
Cl
CH3CH2CH2
C2H5
Br


 177
Cl
CH3CH2CH2
C2H5
I


 178
Cl
CH3CH2CH2
C2H5
CF3


 179
Cl
CH3CH2CH2
C2H5
CH3S(O)


 180
Cl
CH3CH2CH2
C2H5
CH3S(O)2


 181
Cl
(CH3)2CH
C2H5
Cl


 182
Cl
(CH3)2CH
C2H5
Br


 183
Cl
(CH3)2CH
C2H5
I


 184
Cl
(CH3)2CH
C2H5
CF3


 185
Cl
(CH3)2CH
C2H5
CH3S(O)


 186
Cl
(CH3)2CH
C2H5
CH3S(O)2


 187
Cl
(CH3)3C
C2H5
Cl


 188
Cl
(CH3)3C
C2H5
Br


 189
Cl
(CH3)3C
C2H5
I


 190
Cl
(CH3)3C
C2H5
CF3


 191
Cl
(CH3)3C
C2H5
CH3S(O)


 192
Cl
(CH3)3C
C2H5
CH3S(O)2


 193
Cl
c-C3H5
C2H5
Cl


 194
Cl
c-C3H5
C2H5
Br


 195
Cl
c-C3H5
C2H5
I


 196
Cl
c-C3H5
C2H5
CF3


 197
Cl
c-C3H5
C2H5
CH3S(O)


 198
Cl
c-C3H5
C2H5
CH3S(O)2


 199
Cl
CHF2CH2
C2H5
Cl


 200
Cl
CHF2CH2
C2H5
Br


 201
Cl
CHF2CH2
C2H5
I


 202
Cl
CHF2CH2
C2H5
CF3


 203
Cl
CHF2CH2
C2H5
CH3S(O)


 204
Cl
CHF2CH2
C2H5
CH3S(O)2


 205
Cl
CF3CH2
C2H5
Cl


 206
Cl
CF3CH2
C2H5
Br


 207
Cl
CF3CH2
C2H5
I


 208
Cl
CF3CH2
C2H5
CF3


 209
Cl
CF3CH2
C2H5
CH3S(O)


 210
Cl
CF3CH2
C2H5
CH3S(O)2


 211
Cl
CH3O
C2H5
Cl


 212
Cl
CH3O
C2H5
Br


 213
Cl
CH3O
C2H5
I


 214
Cl
CH3O
C2H5
CF3


 215
Cl
CH3O
C2H5
CH3S(O)


 216
Cl
CH3O
C2H5
CH3S(O)2


 217
Cl
C6H5
C2H5
Cl


 218
Cl
C6H5
C2H5
Br


 219
Cl
C6H5
C2H5
I


 220
Cl
C6H5
C2H5
CF3


 221
Cl
C6H5
C2H5
CH3S(O)


 222
Cl
C6H5
C2H5
CH3S(O)2


 223
Cl
4-Cl-C6H4
C2H5
Cl


 224
Cl
4-Cl-C6H4
C2H5
Br


 225
Cl
4-Cl-C6H4
C2H5
I


 226
Cl
4-Cl-C6H4
C2H5
CF3


 227
Cl
4-Cl-C6H4
C2H5
CH3S(O)


 228
Cl
4-Cl-C6H4
C2H5
CH3S(O)2


 229
Cl
4-CH3-C6H4
C2H5
Cl


 230
Cl
4-CH3-C6H4
C2H5
Br


 231
Cl
4-CH3-C6H4
C2H5
I


 232
Cl
4-CH3-C6H4
C2H5
CF3


 233
Cl
4-CH3-C6H4
C2H5
CH3S(O)


 234
Cl
4-CH3-C6H4
C2H5
CH3S(O)2


 235
Cl
4-CH3O-C6H4
C2H5
Cl


 236
Cl
4-CH3O-C6H4
C2H5
Br


 237
Cl
4-CH3O-C6H4
C2H5
I


 238
Cl
4-CH3O-C6H4
C2H5
CF3


 239
Cl
4-CH3O-C6H4
C2H5
CH3S(O)


 240
Cl
4-CH3O-C6H4
C2H5
CH3S(O)2


 241
Cl
2,6-(CH3)2-C6H3
C2H5
Cl


 242
Cl
2,6-(CH3)2-C6H3
C2H5
Br


 243
Cl
2,6-(CH3)2-C6H3
C2H5
I


 244
Cl
2,6-(CH3)2-C6H3
C2H5
CF3


 245
Cl
2,6-(CH3)2-C6H3
C2H5
CH3S(O)


 246
Cl
2,6-(CH3)2-C6H3
C2H5
CH3S(O)2


 247
Cl
CH3CH2CH2
CH3CH2CH2
Cl


 248
Cl
CH3CH2CH2
CH3CH2CH2
Br


 249
Cl
CH3CH2CH2
CH3CH2CH2
I


 250
Cl
CH3CH2CH2
CH3CH2CH2
CF3


 251
Cl
CH3CH2CH2
CH3CH2CH2
CH3S(O)


 252
Cl
CH3CH2CH2
CH3CH2CH2
CH3S(O)2


 253
Cl
(CH3)2CH
CH3CH2CH2
Cl


 254
Cl
(CH3)2CH
CH3CH2CH2
Br


 255
Cl
(CH3)2CH
CH3CH2CH2
I


 256
Cl
(CH3)2CH
CH3CH2CH2
CF3


 257
Cl
(CH3)2CH
CH3CH2CH2
CH3S(O)


 258
Cl
(CH3)2CH
CH3CH2CH2
CH3S(O)2


 259
Cl
(CH3)3C
CH3CH2CH2
Cl


 260
Cl
(CH3)3C
CH3CH2CH2
Br


 261
Cl
(CH3)3C
CH3CH2CH2
I


 262
Cl
(CH3)3C
CH3CH2CH2
CF3


 263
Cl
(CH3)3C
CH3CH2CH2
CH3S(O)


 264
Cl
(CH3)3C
CH3CH2CH2
CH3S(O)2


 265
Cl
c-C3H5
CH3CH2CH2
Cl


 266
Cl
c-C3H5
CH3CH2CH2
Br


 267
Cl
c-C3H5
CH3CH2CH2
I


 268
Cl
c-C3H5
CH3CH2CH2
CF3


 269
Cl
c-C3H5
CH3CH2CH2
CH3S(O)


 270
Cl
c-C3H5
CH3CH2CH2
CH3S(O)2


 271
Cl
CHF2CH2
CH3CH2CH2
Cl


 272
Cl
CHF2CH2
CH3CH2CH2
Br


 273
Cl
CHF2CH2
CH3CH2CH2
I


 274
Cl
CHF2CH2
CH3CH2CH2
CF3


 275
Cl
CHF2CH2
CH3CH2CH2
CH3S(O)


 276
Cl
CHF2CH2
CH3CH2CH2
CH3S(O)2


 277
Cl
CF3CH2
CH3CH2CH2
Cl


 278
Cl
CF3CH2
CH3CH2CH2
Br


 279
Cl
CF3CH2
CH3CH2CH2
I


 280
Cl
CF3CH2
CH3CH2CH2
CF3


 281
Cl
CF3CH2
CH3CH2CH2
CH3S(O)


 282
Cl
CF3CH2
CH3CH2CH2
CH3S(O)2


 283
Cl
CH3O
CH3CH2CH2
Cl


 284
Cl
CH3O
CH3CH2CH2
Br


 285
Cl
CH3O
CH3CH2CH2
I


 286
Cl
CH3O
CH3CH2CH2
CF3


 287
Cl
CH3O
CH3CH2CH2
CH3S(O)


 288
Cl
CH3O
CH3CH2CH2
CH3S(O)2


 289
Cl
C6H5
CH3CH2CH2
Cl


 290
Cl
C6H5
CH3CH2CH2
Br


 291
Cl
C6H5
CH3CH2CH2
I


 292
Cl
C6H5
CH3CH2CH2
CF3


 293
Cl
C6H5
CH3CH2CH2
CH3S(O)


 294
Cl
C6H5
CH3CH2CH2
CH3S(O)2


 295
Cl
4-Cl-C6H4
CH3CH2CH2
Cl


 296
Cl
4-Cl-C6H4
CH3CH2CH2
Br


 297
Cl
4-Cl-C6H4
CH3CH2CH2
I


 298
Cl
4-Cl-C6H4
CH3CH2CH2
CF3


 299
Cl
4-Cl-C6H4
CH3CH2CH2
CH3S(O)


 300
Cl
4-Cl-C6H4
CH3CH2CH2
CH3S(O)2


 301
Cl
4-CH3-C6H4
CH3CH2CH2
Cl


 302
Cl
4-CH3-C6H4
CH3CH2CH2
Br


 303
Cl
4-CH3-C6H4
CH3CH2CH2
I


 304
Cl
4-CH3-C6H4
CH3CH2CH2
CF3


 305
Cl
4-CH3-C6H4
CH3CH2CH2
CH3S(O)


 306
Cl
4-CH3-C6H4
CH3CH2CH2
CH3S(O)2


 307
Cl
4-CH3O-C6H4
CH3CH2CH2
Cl


 308
Cl
4-CH3O-C6H4
CH3CH2CH2
Br


 309
Cl
4-CH3O-C6H4
CH3CH2CH2
I


 310
Cl
4-CH3O-C6H4
CH3CH2CH2
CF3


 311
Cl
4-CH3O-C6H4
CH3CH2CH2
CH3S(O)


 312
Cl
4-CH3O-C6H4
CH3CH2CH2
CH3S(O)2


 313
Cl
2,6-(CH3)2-C6H3
CH3CH2CH2
Cl


 314
Cl
2,6-(CH3)2-C6H3
CH3CH2CH2
Br


 315
Cl
2,6-(CH3)2-C6H3
CH3CH2CH2
I


 316
Cl
2,6-(CH3)2-C6H3
CH3CH2CH2
CF3


 317
Cl
2,6-(CH3)2-C6H3
CH3CH2CH2
CH3S(O)


 318
Cl
2,6-(CH3)2-C6H3
CH3CH2CH2
CH3S(O)2


 319
Cl
(CH3)2CH
(CH3)2CH
Cl


 320
Cl
(CH3)2CH
(CH3)2CH
Br


 321
Cl
(CH3)2CH
(CH3)2CH
I


 322
Cl
(CH3)2CH
(CH3)2CH
CF3


 323
Cl
(CH3)2CH
(CH3)2CH
CH3S(O)


 324
Cl
(CH3)2CH
(CH3)2CH
CH3S(O)2


 325
Cl
c-C3H5
(CH3)2CH
Cl


 326
Cl
c-C3H5
(CH3)2CH
Br


 327
Cl
c-C3H5
(CH3)2CH
I


 328
Cl
c-C3H5
(CH3)2CH
CF3


 329
Cl
c-C3H5
(CH3)2CH
CH3S(O)


 330
Cl
c-C3H5
(CH3)2CH
CH3S(O)2


 331
Cl
CHF2CH2
(CH3)2CH
Cl


 332
Cl
CHF2CH2
(CH3)2CH
Br


 333
Cl
CHF2CH2
(CH3)2CH
I


 334
Cl
CHF2CH2
(CH3)2CH
CF3


 335
Cl
CHF2CH2
(CH3)2CH
CH3S(O)


 336
Cl
CHF2CH2
(CH3)2CH
CH3S(O)2


 337
Cl
CF3CH2
(CH3)2CH
Cl


 338
Cl
CF3CH2
(CH3)2CH
Br


 339
Cl
CF3CH2
(CH3)2CH
I


 340
Cl
CF3CH2
(CH3)2CH
CF3


 341
Cl
CF3CH2
(CH3)2CH
CH3S(O)


 342
Cl
CF3CH2
(CH3)2CH
CH3S(O)2


 343
Cl
CH3O
(CH3)2CH
Cl


 344
Cl
CH3O
(CH3)2CH
Br


 345
Cl
CH3O
(CH3)2CH
I


 346
Cl
CH3O
(CH3)2CH
CF3


 347
Cl
CH3O
(CH3)2CH
CH3S(O)


 348
Cl
CH3O
(CH3)2CH
CH3S(O)2


 349
Cl
C6H5
(CH3)2CH
Cl


 350
Cl
C6H5
(CH3)2CH
Br


 351
Cl
C6H5
(CH3)2CH
I


 352
Cl
C6H5
(CH3)2CH
CF3


 353
Cl
C6H5
(CH3)2CH
CH3S(O)


 354
Cl
C6H5
(CH3)2CH
CH3S(O)2


 355
Cl
4-Cl-C6H4
(CH3)2CH
Cl


 356
Cl
4-Cl-C6H4
(CH3)2CH
Br


 357
Cl
4-Cl-C6H4
(CH3)2CH
I


 358
Cl
4-Cl-C6H4
(CH3)2CH
CF3


 359
Cl
4-Cl-C6H4
(CH3)2CH
CH3S(O)


 360
Cl
4-Cl-C6H4
(CH3)2CH
CH3S(O)2


 361
Cl
4-CH3-C6H4
(CH3)2CH
Cl


 362
Cl
4-CH3-C6H4
(CH3)2CH
Br


 363
Cl
4-CH3-C6H4
(CH3)2CH
I


 364
Cl
4-CH3-C6H4
(CH3)2CH
CF3


 365
Cl
4-CH3-C6H4
(CH3)2CH
CH3S(O)


 366
Cl
4-CH3-C6H4
(CH3)2CH
CH3S(O)2


 367
Cl
4-CH3O-C6H4
(CH3)2CH
Cl


 368
Cl
4-CH3O-C6H4
(CH3)2CH
Br


 369
Cl
4-CH3O-C6H4
(CH3)2CH
I


 370
Cl
4-CH3O-C6H4
(CH3)2CH
CF3


 371
Cl
4-CH3O-C6H4
(CH3)2CH
CH3S(O)


 372
Cl
4-CH3O-C6H4
(CH3)2CH
CH3S(O)2


 373
Cl
2,6-(CH3)2-C6H3
(CH3)2CH
Cl


 374
Cl
2,6-(CH3)2-C6H3
(CH3)2CH
Br


 375
Cl
2,6-(CH3)2-C6H3
(CH3)2CH
I


 376
Cl
2,6-(CH3)2-C6H3
(CH3)2CH
CF3


 377
Cl
2,6-(CH3)2-C6H3
(CH3)2CH
CH3S(O)


 378
Cl
2,6-(CH3)2-C6H3
(CH3)2CH
CH3S(O)2


 379
Cl
c-C3H5
c-C3H5
Cl


 380
Cl
c-C3H5
c-C3H5
Br


 381
Cl
c-C3H5
c-C3H5
I


 382
Cl
c-C3H5
c-C3H5
CF3


 383
Cl
c-C3H5
c-C3H5
CH3S(O)


 384
Cl
c-C3H5
c-C3H5
CH3S(O)2


 385
Cl
CHF2CH2
c-C3H5
Cl


 386
Cl
CHF2CH2
c-C3H5
Br


 387
Cl
CHF2CH2
c-C3H5
I


 388
Cl
CHF2CH2
c-C3H5
CF3


 389
Cl
CHF2CH2
c-C3H5
CH3S(O)


 390
Cl
CHF2CH2
c-C3H5
CH3S(O)2


 391
Cl
CF3CH2
c-C3H5
Cl


 392
Cl
CF3CH2
c-C3H5
Br


 393
Cl
CF3CH2
c-C3H5
I


 394
Cl
CF3CH2
c-C3H5
CF3


 395
Cl
CF3CH2
c-C3H5
CH3S(O)


 396
Cl
CF3CH2
c-C3H5
CH3S(O)2


 397
Cl
CH3O
c-C3H5
Cl


 398
Cl
CH3O
c-C3H5
Br


 399
Cl
CH3O
c-C3H5
I


 400
Cl
CH3O
c-C3H5
CF3


 401
Cl
CH3O
c-C3H5
CH3S(O)


 402
Cl
CH3O
c-C3H5
CH3S(O)2


 403
Cl
C6H5
c-C3H5
Cl


 404
Cl
C6H5
c-C3H5
Br


 405
Cl
C6H5
c-C3H5
I


 406
Cl
C6H5
c-C3H5
CF3


 407
Cl
C6H5
c-C3H5
CH3S(O)


 408
Cl
C6H5
c-C3H5
CH3S(O)2


 409
Cl
4-Cl-C6H4
c-C3H5
Cl


 410
Cl
4-Cl-C6H4
c-C3H5
Br


 411
Cl
4-Cl-C6H4
c-C3H5
I


 412
Cl
4-Cl-C6H4
c-C3H5
CF3


 413
Cl
4-Cl-C6H4
c-C3H5
CH3S(O)


 414
Cl
4-Cl-C6H4
c-C3H5
CH3S(O)2


 415
Cl
4-CH3O-C6H4
c-C3H5
Cl


 416
Cl
4-CH3O-C6H4
c-C3H5
Br


 417
Cl
4-CH3O-C6H4
c-C3H5
I


 418
Cl
4-CH3O-C6H4
c-C3H5
CF3


 419
Cl
4-CH3O-C6H4
c-C3H5
CH3S(O)


 420
Cl
4-CH3O-C6H4
c-C3H5
CH3S(O)2


 421
Cl
4-CH3O-C6H4
c-C3H5
Cl


 422
Cl
4-CH3O-C6H4
c-C3H5
Br


 423
Cl
4-CH3O-C6H4
c-C3H5
I


 424
Cl
4-CH3O-C6H4
c-C3H5
CF3


 425
Cl
4-CH3O-C6H4
c-C3H5
CH3S(O)


 426
Cl
4-CH3O-C6H4
c-C3H5
CH3S(O)2


 427
Cl
2,6-(CH3)2-C6H3
c-C3H5
Cl


 428
Cl
2,6-(CH3)2-C6H3
c-C3H5
Br


 429
Cl
2,6-(CH3)2-C6H3
c-C3H5
I


 430
Cl
2,6-(CH3)2-C6H3
c-C3H5
CF3


 431
Cl
2,6-(CH3)2-C6H3
c-C3H5
CH3S(O)


 432
Cl
2,6-(CH3)2-C6H3
c-C3H5
CH3S(O)2


 433
Cl
(CH3)3C
CHF2CH2
Cl


 434
Cl
(CH3)3C
CHF2CH2
Br


 435
Cl
(CH3)3C
CHF2CH2
I


 436
Cl
(CH3)3C
CHF2CH2
CF3


 437
Cl
(CH3)3C
CHF2CH2
CH3S(O)


 438
Cl
(CH3)3C
CHF2CH2
CH3S(O)2


 439
Cl
CHF2CH2
CHF2CH2
Cl


 440
Cl
CHF2CH2
CHF2CH2
Br


 441
Cl
CHF2CH2
CHF2CH2
I


 442
Cl
CHF2CH2
CHF2CH2
CF3


 443
Cl
CHF2CH2
CHF2CH2
CH3S(O)


 444
Cl
CHF2CH2
CHF2CH2
CH3S(O)2


 445
Cl
CF3CH2
CHF2CH2
Cl


 446
Cl
CF3CH2
CHF2CH2
Br


 447
Cl
CF3CH2
CHF2CH2
I


 448
Cl
CF3CH2
CHF2CH2
CF3


 449
Cl
CF3CH2
CHF2CH2
CH3S(O)


 450
Cl
CF3CH2
CHF2CH2
CH3S(O)2


 451
Cl
CH3O
CHF2CH2
Cl


 452
Cl
CH3O
CHF2CH2
Br


 453
Cl
CH3O
CHF2CH2
I


 454
Cl
CH3O
CHF2CH2
CF3


 455
Cl
CH3O
CHF2CH2
CH3S(O)


 456
Cl
CH3O
CHF2CH2
CH3S(O)2


 457
Cl
C6H5
CHF2CH2
Cl


 458
Cl
C6H5
CHF2CH2
Br


 459
Cl
C6H5
CHF2CH2
I


 460
Cl
C6H5
CHF2CH2
CF3


 461
Cl
C6H5
CHF2CH2
CH3S(O)


 462
Cl
C6H5
CHF2CH2
CH3S(O)2


 463
Cl
4-Cl-C6H4
CHF2CH2
Cl


 464
Cl
4-Cl-C6H4
CHF2CH2
Br


 465
Cl
4-Cl-C6H4
CHF2CH2
I


 466
Cl
4-Cl-C6H4
CHF2CH2
CF3


 467
Cl
4-Cl-C6H4
CHF2CH2
CH3S(O)


 468
Cl
4-Cl-C6H4
CHF2CH2
CH3S(O)2


 469
Cl
4-CH3-C6H4
CHF2CH2
Cl


 470
Cl
4-CH3-C6H4
CHF2CH2
Br


 471
Cl
4-CH3-C6H4
CHF2CH2
I


 472
Cl
4-CH3-C6H4
CHF2CH2
CF3


 473
Cl
4-CH3-C6H4
CHF2CH2
CH3S(O)


 474
Cl
4-CH3-C6H4
CHF2CH2
CH3S(O)2


 475
Cl
4-CH3O-C6H4
CHF2CH2
Cl


 476
Cl
4-CH3O-C6H4
CHF2CH2
Br


 477
Cl
4-CH3O-C6H4
CHF2CH2
I


 478
Cl
4-CH3O-C6H4
CHF2CH2
CF3


 479
Cl
4-CH3O-C6H4
CHF2CH2
CH3S(O)


 480
Cl
4-CH3O-C6H4
CHF2CH2
CH3S(O)2


 481
Cl
2,6-(CH3)2-C6H3
CHF2CH2
Cl


 482
Cl
2,6-(CH3)2-C6H3
CHF2CH2
Br


 483
Cl
2,6-(CH3)2-C6H3
CHF2CH2
I


 484
Cl
2,6-(CH3)2-C6H3
CHF2CH2
CF3


 485
Cl
2,6-(CH3)2-C6H3
CHF2CH2
CH3S(O)


 486
Cl
2,6-(CH3)2-C6H3
CHF2CH2
CH3S(O)2


 487
Cl
(CH3)3C
CF3CH2
Cl


 488
Cl
(CH3)3C
CF3CH2
Br


 489
Cl
(CH3)3C
CF3CH2
I


 490
Cl
(CH3)3C
CF3CH2
CF3


 491
Cl
(CH3)3C
CF3CH2
CH3S(O)


 492
Cl
(CH3)3C
CF3CH2
CH3S(O)2


 493
Cl
CF3CH2
CF3CH2
Cl


 494
Cl
CF3CH2
CF3CH2
Br


 495
Cl
CF3CH2
CF3CH2
I


 496
Cl
CF3CH2
CF3CH2
CF3


 497
Cl
CF3CH2
CF3CH2
CH3S(O)


 498
Cl
CF3CH2
CF3CH2
CH3S(O)2


 499
Cl
CH3O
CF3CH2
Cl


 500
Cl
CH3O
CF3CH2
Br


 501
Cl
CH3O
CF3CH2
I


 502
Cl
CH3O
CF3CH2
CF3


 503
Cl
CH3O
CF3CH2
CH3S(O)


 504
Cl
CH3O
CF3CH2
CH3S(O)2


 505
Cl
C6H5
CF3CH2
Cl


 506
Cl
C6H5
CF3CH2
Br


 507
Cl
C6H5
CF3CH2
I


 508
Cl
C6H5
CF3CH2
CF3


 509
Cl
C6H5
CF3CH2
CH3S(O)


 510
Cl
C6H5
CF3CH2
CH3S(O)2


 511
Cl
4-Cl-C6H4
CF3CH2
Cl


 512
Cl
4-Cl-C6H4
CF3CH2
Br


 513
Cl
4-Cl-C6H4
CF3CH2
I


 514
Cl
4-Cl-C6H4
CF3CH2
CF3


 515
Cl
4-Cl-C6H4
CF3CH2
CH3S(O)


 516
Cl
4-Cl-C6H4
CF3CH2
CH3S(O)2


 517
Cl
4-CH3-C6H4
CF3CH2
Cl


 518
Cl
4-CH3-C6H4
CF3CH2
Br


 519
Cl
4-CH3-C6H4
CF3CH2
I


 520
Cl
4-CH3-C6H4
CF3CH2
CF3


 521
Cl
4-CH3-C6H4
CF3CH2
CH3S(O)


 522
Cl
4-CH3-C6H4
CF3CH2
CH3S(O)2


 523
Cl
4-CH3O-C6H4
CF3CH2
Cl


 524
Cl
4-CH3O-C6H4
CF3CH2
Br


 525
Cl
4-CH3O-C6H4
CF3CH2
I


 526
Cl
4-CH3O-C6H4
CF3CH2
CF3


 527
Cl
4-CH3O-C6H4
CF3CH2
CH3S(O)


 528
Cl
4-CH3O-C6H4
CF3CH2
CH3S(O)2


 529
Cl
2,6-(CH3)2-C6H3
CF3CH2
Cl


 530
Cl
2,6-(CH3)2-C6H3
CF3CH2
Br


 531
Cl
2,6-(CH3)2-C6H3
CF3CH2
I


 532
Cl
2,6-(CH3)2-C6H3
CF3CH2
CF3


 533
Cl
2,6-(CH3)2-C6H3
CF3CH2
CH3S(O)


 534
Cl
2,6-(CH3)2-C6H3
CF3CH2
CH3S(O)2













 535
Cl


embedded image


Cl





 536
Cl


embedded image


Br





 537
Cl


embedded image


I





 538
Cl


embedded image


CF3





 539
Cl


embedded image


CH3S(O)





 540
Cl


embedded image


CH3S(O)2





 541
Cl


embedded image


Cl





 542
Cl


embedded image


Br





 543
Cl


embedded image


I





 544
Cl


embedded image


CF3





 545
Cl


embedded image


CH3S(O)





 546
Cl


embedded image


CH3S(O)2





 547
Cl


embedded image


Cl





 548
Cl


embedded image


Br





 549
Cl


embedded image


I





 550
Cl


embedded image


CF3





 551
Cl


embedded image


CH3S(O)





 552
Cl


embedded image


CH3S(O)2














 553
CH3
CH3
H
Cl


 554
CH3
CH3
H
Br


 555
CH3
CH3
H
I


 556
CH3
CH3
H
CF3


 557
CH3
CH3
H
CH3S(O)


 558
CH3
CH3
H
CH3S(O)2


 559
CH3
C2H5
H
Cl


 560
CH3
C2H5
H
Br


 561
CH3
C2H5
H
I


 562
CH3
C2H5
H
CF3


 563
CH3
C2H5
H
CH3S(O)


 564
CH3
C2H5
H
CH3S(O)2


 565
CH3
CH3CH2CH2
H
Cl


 566
CH3
CH3CH2CH2
H
Br


 567
CH3
CH3CH2CH2
H
I


 568
CH3
CH3CH2CH2
H
CF3


 569
CH3
CH3CH2CH2
H
CH3S(O)


 570
CH3
CH3CH2CH2
H
CH3S(O)2


 571
CH3
(CH3)2CH
H
Cl


 572
CH3
(CH3)2CH
H
Br


 573
CH3
(CH3)2CH
H
I


 574
CH3
(CH3)2CH
H
CF3


 575
CH3
(CH3)2CH
H
CH3S(O)


 576
CH3
(CH3)2CH
H
CH3S(O)2


 577
CH3
(CH3)3C
H
Cl


 578
CH3
(CH3)3C
H
Br


 579
CH3
(CH3)3C
H
I


 580
CH3
(CH3)3C
H
CF3


 581
CH3
(CH3)3C
H
CH3S(O)


 582
CH3
(CH3)3C
H
CH3S(O)2


 583
CH3
c-C3H5
H
Cl


 584
CH3
c-C3H5
H
Br


 585
CH3
c-C3H5
H
I


 586
CH3
c-C3H5
H
CF3


 587
CH3
c-C3H5
H
CH3S(O)


 588
CH3
c-C3H5
H
CH3S(O)2


 589
CH3
CHF2CH2
H
Cl


 590
CH3
CHF2CH2
H
Br


 591
CH3
CHF2CH2
H
I


 592
CH3
CHF2CH2
H
CF3


 593
CH3
CHF2CH2
H
CH3S(O)


 594
CH3
CHF2CH2
H
CH3S(O)2


 595
CH3
CF3CH2
H
Cl


 596
CH3
CF3CH2
H
Br


 597
CH3
CF3CH2
H
I


 598
CH3
CF3CH2
H
CF3


 599
CH3
CF3CH2
H
CH3S(O)


 600
CH3
CF3CH2
H
CH3S(O)2


 601
CH3
CH3O
H
Cl


 602
CH3
CH3O
H
Br


 603
CH3
CH3O
H
I


 604
CH3
CH3O
H
CF3


 605
CH3
CH3O
H
CH3S(O)


 606
CH3
CH3O
H
CH3S(O)2


 607
CH3
C6H5
H
Cl


 608
CH3
C6H5
H
Br


 609
CH3
C6H5
H
I


 610
CH3
C6H5
H
CF3


 611
CH3
C6H5
H
CH3S(O)


 612
CH3
C6H5
H
CH3S(O)2


 613
CH3
4-Cl-C6H4
H
Cl


 614
CH3
4-Cl-C6H4
H
Br


 615
CH3
4-Cl-C6H4
H
I


 616
CH3
4-Cl-C6H4
H
CF3


 617
CH3
4-Cl-C6H4
H
CH3S(O)


 618
CH3
4-Cl-C6H4
H
CH3S(O)2


 619
CH3
4-CH3-C6H4
H
Cl


 620
CH3
4-CH3-C6H4
H
Br


 621
CH3
4-CH3-C6H4
H
I


 622
CH3
4-CH3-C6H4
H
CF3


 623
CH3
4-CH3-C6H4
H
CH3S(O)


 624
CH3
4-CH3-C6H4
H
CH3S(O)2


 625
CH3
4-CH3O-C6H4
H
Cl


 626
CH3
4-CH3O-C6H4
H
Br


 627
CH3
4-CH3O-C6H4
H
I


 628
CH3
4-CH3O-C6H4
H
CF3


 629
CH3
4-CH3O-C6H4
H
CH3S(O)


 630
CH3
4-CH3O-C6H4
H
CH3S(O)2


 631
CH3
2,6-(CH3)2-C6H3
H
Cl


 632
CH3
2,6-(CH3)2-C6H3
H
Br


 633
CH3
2,6-(CH3)2-C6H3
H
I


 634
CH3
2,6-(CH3)2-C6H3
H
CF3


 635
CH3
2,6-(CH3)2-C6H3
H
CH3S(O)


 636
CH3
2,6-(CH3)2-C6H3
H
CH3S(O)2


 637
CH3
CH3
CH3
Cl


 638
CH3
CH3
CH3
Br


 639
CH3
CH3
CH3
I


 640
CH3
CH3
CH3
CF3


 641
CH3
CH3
CH3
CH3S(O)


 642
CH3
CH3
CH3
CH3S(O)2


 643
CH3
C2H5
CH3
Cl


 644
CH3
C2H5
CH3
Br


 645
CH3
C2H5
CH3
I


 646
CH3
C2H5
CH3
CF3


 647
CH3
C2H5
CH3
CH3S(O)


 648
CH3
C2H5
CH3
CH3S(O)2


 649
CH3
CH3CH2CH2
CH3
Cl


 650
CH3
CH3CH2CH2
CH3
Br


 651
CH3
CH3CH2CH2
CH3
I


 652
CH3
CH3CH2CH2
CH3
CF3


 653
CH3
CH3CH2CH2
CH3
CH3S(O)


 654
CH3
CH3CH2CH2
CH3
CH3S(O)2


 655
CH3
(CH3)2CH
CH3
Cl


 656
CH3
(CH3)2CH
CH3
Br


 657
CH3
(CH3)2CH
CH3
I


 658
CH3
(CH3)2CH
CH3
CF3


 659
CH3
(CH3)2CH
CH3
CH3S(O)


 660
CH3
(CH3)2CH
CH3
CH3S(O)2


 661
CH3
(CH3)3C
CH3
Cl


 662
CH3
(CH3)3C
CH3
Br


 663
CH3
(CH3)3C
CH3
I


 664
CH3
(CH3)3C
CH3
CF3


 665
CH3
(CH3)3C
CH3
CH3S(O)


 666
CH3
(CH3)3C
CH3
CH3S(O)2


 667
CH3
c-C3H5
CH3
Cl


 668
CH3
c-C3H5
CH3
Br


 669
CH3
c-C3H5
CH3
I


 670
CH3
c-C3H5
CH3
CF3


 671
CH3
c-C3H5
CH3
CH3S(O)


 672
CH3
c-C3H5
CH3
CH3S(O)2


 673
CH3
CHF2CH2
CH3
Cl


 674
CH3
CHF2CH2
CH3
Br


 675
CH3
CHF2CH2
CH3
I


 676
CH3
CHF2CH2
CH3
CF3


 677
CH3
CHF2CH2
CH3
CH3S(O)


 678
CH3
CHF2CH2
CH3
CH3S(O)2


 679
CH3
CF3CH2
CH3
Cl


 680
CH3
CF3CH2
CH3
Br


 681
CH3
CF3CH2
CH3
I


 682
CH3
CF3CH2
CH3
CF3


 683
CH3
CF3CH2
CH3
CH3S(O)


 684
CH3
CF3CH2
CH3
CH3S(O)2


 685
CH3
CH3O
CH3
Cl


 686
CH3
CH3O
CH3
Br


 687
CH3
CH3O
CH3
I


 688
CH3
CH3O
CH3
CF3


 689
CH3
CH3O
CH3
CH3S(O)


 690
CH3
CH3O
CH3
CH3S(O)2


 691
CH3
C6H5
CH3
Cl


 692
CH3
C6H5
CH3
Br


 693
CH3
C6H5
CH3
I


 694
CH3
C6H5
CH3
CF3


 695
CH3
C6H5
CH3
CH3S(O)


 696
CH3
C6H5
CH3
CH3S(O)2


 697
CH3
4-Cl-C6H4
CH3
Cl


 698
CH3
4-Cl-C6H4
CH3
Br


 699
CH3
4-Cl-C6H4
CH3
I


 700
CH3
4-Cl-C6H4
CH3
CF3


 701
CH3
4-Cl-C6H4
CH3
CH3S(O)


 702
CH3
4-Cl-C6H4
CH3
CH3S(O)2


 703
CH3
4-CH3-C6H4
CH3
Cl


 704
CH3
4-CH3-C6H4
CH3
Br


 705
CH3
4-CH3-C6H4
CH3
I


 706
CH3
4-CH3-C6H4
CH3
CF3


 707
CH3
4-CH3-C6H4
CH3
CH3S(O)


 708
CH3
4-CH3-C6H4
CH3
CH3S(O)2


 709
CH3
4-CH3O-C6H4
CH3
Cl


 710
CH3
4-CH3O-C6H4
CH3
Br


 711
CH3
4-CH3O-C6H4
CH3
I


 712
CH3
4-CH3O-C6H4
CH3
CF3


 713
CH3
4-CH3O-C6H4
CH3
CH3S(O)


 714
CH3
4-CH3O-C6H4
CH3
CH3S(O)2


 715
CH3
2,6-(CH3)2-C6H3
CH3
Cl


 716
CH3
2,6-(CH3)2-C6H3
CH3
Br


 717
CH3
2,6-(CH3)2-C6H3
CH3
I


 718
CH3
2,6-(CH3)2-C6H3
CH3
CF3


 719
CH3
2,6-(CH3)2-C6H3
CH3
CH3S(O)


 720
CH3
2,6-(CH3)2-C6H3
CH3
CH3S(O)2


 721
CH3
C2H5
C2H5
Cl


 722
CH3
C2H5
C2H5
Br


 723
CH3
C2H5
C2H5
I


 724
CH3
C2H5
C2H5
CF3


 725
CH3
C2H5
C2H5
CH3S(O)


 726
CH3
C2H5
C2H5
CH3S(O)2


 727
CH3
CH3CH2CH2
C2H5
Cl


 728
CH3
CH3CH2CH2
C2H5
Br


 729
CH3
CH3CH2CH2
C2H5
I


 730
CH3
CH3CH2CH2
C2H5
CF3


 731
CH3
CH3CH2CH2
C2H5
CH3S(O)


 732
CH3
CH3CH2CH2
C2H5
CH3S(O)2


 733
CH3
(CH3)2CH
C2H5
Cl


 734
CH3
(CH3)2CH
C2H5
Br


 735
CH3
(CH3)2CH
C2H5
I


 736
CH3
(CH3)2CH
C2H5
CF3


 737
CH3
(CH3)2CH
C2H5
CH3S(O)


 738
CH3
(CH3)2CH
C2H5
CH3S(O)2


 739
CH3
(CH3)3C
C2H5
Cl


 740
CH3
(CH3)3C
C2H5
Br


 741
CH3
(CH3)3C
C2H5
I


 742
CH3
(CH3)3C
C2H5
CF3


 743
CH3
(CH3)3C
C2H5
CH3S(O)


 744
CH3
(CH3)3C
C2H5
CH3S(O)2


 745
CH3
c-C3H5
C2H5
Cl


 746
CH3
c-C3H5
C2H5
Br


 747
CH3
c-C3H5
C2H5
I


 748
CH3
c-C3H5
C2H5
CF3


 749
CH3
c-C3H5
C2H5
CH3S(O)


 750
CH3
c-C3H5
C2H5
CH3S(O)2


 751
CH3
CHF2CH2
C2H5
Cl


 752
CH3
CHF2CH2
C2H5
Br


 753
CH3
CHF2CH2
C2H5
I


 754
CH3
CHF2CH2
C2H5
CF3


 755
CH3
CHF2CH2
C2H5
CH3S(O)


 756
CH3
CHF2CH2
C2H5
CH3S(O)2


 757
CH3
CF3CH2
C2H5
Cl


 758
CH3
CF3CH2
C2H5
Br


 759
CH3
CF3CH2
C2H5
I


 760
CH3
CF3CH2
C2H5
CF3


 761
CH3
CF3CH2
C2H5
CH3S(O)


 762
CH3
CF3CH2
C2H5
CH3S(O)2


 763
CH3
CH3O
C2H5
Cl


 764
CH3
CH3O
C2H5
Br


 765
CH3
CH3O
C2H5
I


 766
CH3
CH3O
C2H5
CF3


 767
CH3
CH3O
C2H5
CH3S(O)


 768
CH3
CH3O
C2H5
CH3S(O)2


 769
CH3
C6H5
C2H5
Cl


 770
CH3
C6H5
C2H5
Br


 771
CH3
C6H5
C2H5
I


 772
CH3
C6H5
C2H5
CF3


 773
CH3
C6H5
C2H5
CH3S(O)


 774
CH3
C6H5
C2H5
CH3S(O)2


 775
CH3
4-Cl-C6H4
C2H5
Cl


 776
CH3
4-Cl-C6H4
C2H5
Br


 777
CH3
4-Cl-C6H4
C2H5
I


 778
CH3
4-Cl-C6H4
C2H5
CF3


 779
CH3
4-Cl-C6H4
C2H5
CH3S(O)


 780
CH3
4-Cl-C6H4
C2H5
CH3S(O)2


 781
CH3
4-CH3-C6H4
C2H5
Cl


 782
CH3
4-CH3-C6H4
C2H5
Br


 783
CH3
4-CH3-C6H4
C2H5
I


 784
CH3
4-CH3-C6H4
C2H5
CF3


 785
CH3
4-CH3-C6H4
C2H5
CH3S(O)


 786
CH3
4-CH3-C6H4
C2H5
CH3S(O)2


 787
CH3
4-CH3O-C6H4
C2H5
Cl


 788
CH3
4-CH3O-C6H4
C2H5
Br


 789
CH3
4-CH3O-C6H4
C2H5
I


 790
CH3
4-CH3O-C6H4
C2H5
CF3


 791
CH3
4-CH3O-C6H4
C2H5
CH3S(O)


 792
CH3
4-CH3O-C6H4
C2H5
CH3S(O)2


 793
CH3
2,6-(CH3)2-C6H3
C2H5
Cl


 794
CH3
2,6-(CH3)2-C6H3
C2H5
Br


 795
CH3
2,6-(CH3)2-C6H3
C2H5
I


 796
CH3
2,6-(CH3)2-C6H3
C2H5
CF3


 797
CH3
2,6-(CH3)2-C6H3
C2H5
CH3S(O)


 798
CH3
2,6-(CH3)2-C6H3
C2H5
CH3S(O)2


 799
CH3
CH3CH2CH2
CH3CH2CH2
Cl


 800
CH3
CH3CH2CH2
CH3CH2CH2
Br


 801
CH3
CH3CH2CH2
CH3CH2CH2
I


 802
CH3
CH3CH2CH2
CH3CH2CH2
CF3


 803
CH3
CH3CH2CH2
CH3CH2CH2
CH3S(O)


 804
CH3
CH3CH2CH2
CH3CH2CH2
CH3S(O)2


 805
CH3
(CH3)2CH
CH3CH2CH2
Cl


 806
CH3
(CH3)2CH
CH3CH2CH2
Br


 807
CH3
(CH3)2CH
CH3CH2CH2
I


 808
CH3
(CH3)2CH
CH3CH2CH2
CF3


 809
CH3
(CH3)2CH
CH3CH2CH2
CH3S(O)


 810
CH3
(CH3)2CH
CH3CH2CH2
CH3S(O)2


 811
CH3
(CH3)3C
CH3CH2CH2
Cl


 812
CH3
(CH3)3C
CH3CH2CH2
Br


 813
CH3
(CH3)3C
CH3CH2CH2
I


 814
CH3
(CH3)3C
CH3CH2CH2
CF3


 815
CH3
(CH3)3C
CH3CH2CH2
CH3S(O)


 816
CH3
(CH3)3C
CH3CH2CH2
CH3S(O)2


 817
CH3
c-C3H5
CH3CH2CH2
Cl


 818
CH3
c-C3H5
CH3CH2CH2
Br


 819
CH3
c-C3H5
CH3CH2CH2
I


 820
CH3
c-C3H5
CH3CH2CH2
CF3


 821
CH3
c-C3H5
CH3CH2CH2
CH3S(O)


 822
CH3
c-C3H5
CH3CH2CH2
CH3S(O)2


 823
CH3
CHF2CH2
CH3CH2CH2
Cl


 824
CH3
CHF2CH2
CH3CH2CH2
Br


 825
CH3
CHF2CH2
CH3CH2CH2
I


 826
CH3
CHF2CH2
CH3CH2CH2
CF3


 827
CH3
CHF2CH2
CH3CH2CH2
CH3S(O)


 828
CH3
CHF2CH2
CH3CH2CH2
CH3S(O)2


 829
CH3
CF3CH2
CH3CH2CH2
Cl


 830
CH3
CF3CH2
CH3CH2CH2
Br


 831
CH3
CF3CH2
CH3CH2CH2
I


 832
CH3
CF3CH2
CH3CH2CH2
CF3


 833
CH3
CF3CH2
CH3CH2CH2
CH3S(O)


 834
CH3
CF3CH2
CH3CH2CH2
CH3S(O)2


 835
CH3
CH3O
CH3CH2CH2
Cl


 836
CH3
CH3O
CH3CH2CH2
Br


 837
CH3
CH3O
CH3CH2CH2
I


 838
CH3
CH3O
CH3CH2CH2
CF3


 839
CH3
CH3O
CH3CH2CH2
CH3S(O)


 840
CH3
CH3O
CH3CH2CH2
CH3S(O)2


 841
CH3
C6H5
CH3CH2CH2
Cl


 842
CH3
C6H5
CH3CH2CH2
Br


 843
CH3
C6H5
CH3CH2CH2
I


 844
CH3
C6H5
CH3CH2CH2
CF3


 845
CH3
C6H5
CH3CH2CH2
CH3S(O)


 846
CH3
C6H5
CH3CH2CH2
CH3S(O)2


 847
CH3
4-Cl-C6H4
CH3CH2CH2
Cl


 848
CH3
4-Cl-C6H4
CH3CH2CH2
Br


 849
CH3
4-Cl-C6H4
CH3CH2CH2
I


 850
CH3
4-Cl-C6H4
CH3CH2CH2
CF3


 851
CH3
4-Cl-C6H4
CH3CH2CH2
CH3S(O)


 852
CH3
4-Cl-C6H4
CH3CH2CH2
CH3S(O)2


 853
CH3
4-CH3-C6H4
CH3CH2CH2
Cl


 854
CH3
4-CH3-C6H4
CH3CH2CH2
Br


 855
CH3
4-CH3-C6H4
CH3CH2CH2
I


 856
CH3
4-CH3-C6H4
CH3CH2CH2
CF3


 857
CH3
4-CH3-C6H4
CH3CH2CH2
CH3S(O)


 858
CH3
4-CH3-C6H4
CH3CH2CH2
CH3S(O)2


 859
CH3
4-CH3O-C6H4
CH3CH2CH2
Cl


 860
CH3
4-CH3O-C6H4
CH3CH2CH2
Br


 861
CH3
4-CH3O-C6H4
CH3CH2CH2
I


 862
CH3
4-CH3O-C6H4
CH3CH2CH2
CF3


 863
CH3
4-CH3O-C6H4
CH3CH2CH2
CH3S(O)


 864
CH3
4-CH3O-C6H4
CH3CH2CH2
CH3S(O)2


 865
CH3
2,6-(CH3)2-C6H3
CH3CH2CH2
Cl


 866
CH3
2,6-(CH3)2-C6H3
CH3CH2CH2
Br


 867
CH3
2,6-(CH3)2-C6H3
CH3CH2CH2
I


 868
CH3
2,6-(CH3)2-C6H3
CH3CH2CH2
CF3


 869
CH3
2,6-(CH3)2-C6H3
CH3CH2CH2
CH3S(O)


 870
CH3
2,6-(CH3)2-C6H3
CH3CH2CH2
CH3S(O)2


 871
CH3
(CH3)2CH
(CH3)2CH
Cl


 872
CH3
(CH3)2CH
(CH3)2CH
Br


 873
CH3
(CH3)2CH
(CH3)2CH
I


 874
CH3
(CH3)2CH
(CH3)2CH
CF3


 875
CH3
(CH3)2CH
(CH3)2CH
CH3S(O)


 876
CH3
(CH3)2CH
(CH3)2CH
CH3S(O)2


 877
CH3
c-C3H5
(CH3)2CH
Cl


 878
CH3
c-C3H5
(CH3)2CH
Br


 879
CH3
c-C3H5
(CH3)2CH
I


 880
CH3
c-C3H5
(CH3)2CH
CF3


 881
CH3
c-C3H5
(CH3)2CH
CH3S(O)


 882
CH3
c-C3H5
(CH3)2CH
CH3S(O)2


 883
CH3
CHF2CH2
(CH3)2CH
Cl


 884
CH3
CHF2CH2
(CH3)2CH
Br


 885
CH3
CHF2CH2
(CH3)2CH
I


 886
CH3
CHF2CH2
(CH3)2CH
CF3


 887
CH3
CHF2CH2
(CH3)2CH
CH3S(O)


 888
CH3
CHF2CH2
(CH3)2CH
CH3S(O)2


 889
CH3
CF3CH2
(CH3)2CH
Cl


 890
CH3
CF3CH2
(CH3)2CH
Br


 891
CH3
CF3CH2
(CH3)2CH
I


 892
CH3
CF3CH2
(CH3)2CH
CF3


 893
CH3
CF3CH2
(CH3)2CH
CH3S(O)


 894
CH3
CF3CH2
(CH3)2CH
CH3S(O)2


 895
CH3
CH3O
(CH3)2CH
Cl


 896
CH3
CH3O
(CH3)2CH
Br


 897
CH3
CH3O
(CH3)2CH
I


 898
CH3
CH3O
(CH3)2CH
CF3


 899
CH3
CH3O
(CH3)2CH
CH3S(O)


 900
CH3
CH3O
(CH3)2CH
CH3S(O)2


 901
CH3
C6H5
(CH3)2CH
Cl


 902
CH3
C6H5
(CH3)2CH
Br


 903
CH3
C6H5
(CH3)2CH
I


 904
CH3
C6H5
(CH3)2CH
CF3


 905
CH3
C6H5
(CH3)2CH
CH3S(O)


 906
CH3
C6H5
(CH3)2CH
CH3S(O)2


 907
CH3
4-Cl-C6H4
(CH3)2CH
Cl


 908
CH3
4-Cl-C6H4
(CH3)2CH
Br


 909
CH3
4-Cl-C6H4
(CH3)2CH
I


 910
CH3
4-Cl-C6H4
(CH3)2CH
CF3


 911
CH3
4-Cl-C6H4
(CH3)2CH
CH3S(O)


 912
CH3
4-Cl-C6H4
(CH3)2CH
CH3S(O)2


 913
CH3
4-CH3-C6H4
(CH3)2CH
Cl


 914
CH3
4-CH3-C6H4
(CH3)2CH
Br


 915
CH3
4-CH3-C6H4
(CH3)2CH
I


 916
CH3
4-CH3-C6H4
(CH3)2CH
CF3


 917
CH3
4-CH3-C6H4
(CH3)2CH
CH3S(O)


 918
CH3
4-CH3-C6H4
(CH3)2CH
CH3S(O)2


 919
CH3
4-CH3O-C6H4
(CH3)2CH
Cl


 920
CH3
4-CH3O-C6H4
(CH3)2CH
Br


 921
CH3
4-CH3O-C6H4
(CH3)2CH
I


 922
CH3
4-CH3O-C6H4
(CH3)2CH
CF3


 923
CH3
4-CH3O-C6H4
(CH3)2CH
CH3S(O)


 924
CH3
4-CH3O-C6H4
(CH3)2CH
CH3S(O)2


 925
CH3
2,6-(CH3)2-C6H3
(CH3)2CH
Cl


 926
CH3
2,6-(CH3)2-C6H3
(CH3)2CH
Br


 927
CH3
2,6-(CH3)2-C6H3
(CH3)2CH
I


 928
CH3
2,6-(CH3)2-C6H3
(CH3)2CH
CF3


 929
CH3
2,6-(CH3)2-C6H3
(CH3)2CH
CH3S(O)


 930
CH3
2,6-(CH3)2-C6H3
(CH3)2CH
CH3S(O)2


 931
CH3
c-C3H5
c-C3H5
Cl


 932
CH3
c-C3H5
c-C3H5
Br


 933
CH3
c-C3H5
c-C3H5
I


 934
CH3
c-C3H5
c-C3H5
CF3


 935
CH3
c-C3H5
c-C3H5
CH3S(O)


 936
CH3
c-C3H5
c-C3H5
CH3S(O)2


 937
CH3
CHF2CH2
c-C3H5
Cl


 938
CH3
CHF2CH2
c-C3H5
Br


 939
CH3
CHF2CH2
c-C3H5
I


 940
CH3
CHF2CH2
c-C3H5
CF3


 941
CH3
CHF2CH2
c-C3H5
CH3S(O)


 942
CH3
CHF2CH2
c-C3H5
CH3S(O)2


 943
CH3
CF3CH2
c-C3H5
Cl


 944
CH3
CF3CH2
c-C3H5
Br


 945
CH3
CF3CH2
c-C3H5
I


 946
CH3
CF3CH2
c-C3H5
CF3


 947
CH3
CF3CH2
c-C3H5
CH3S(O)


 948
CH3
CF3CH2
c-C3H5
CH3S(O)2


 949
CH3
CH3O
c-C3H5
Cl


 950
CH3
CH3O
c-C3H5
Br


 951
CH3
CH3O
c-C3H5
I


 952
CH3
CH3O
c-C3H5
CF3


 953
CH3
CH3O
c-C3H5
CH3S(O)


 954
CH3
CH3O
c-C3H5
CH3S(O)2


 955
CH3
C6H5
c-C3H5
Cl


 956
CH3
C6H5
c-C3H5
Br


 957
CH3
C6H5
c-C3H5
I


 958
CH3
C6H5
c-C3H5
CF3


 959
CH3
C6H5
c-C3H5
CH3S(O)


 960
CH3
C6H5
c-C3H5
CH3S(O)2


 961
CH3
4-Cl-C6H4
c-C3H5
Cl


 962
CH3
4-Cl-C6H4
c-C3H5
Br


 963
CH3
4-Cl-C6H4
c-C3H5
I


 964
CH3
4-Cl-C6H4
c-C3H5
CF3


 965
CH3
4-Cl-C6H4
c-C3H5
CH3S(O)


 966
CH3
4-Cl-C6H4
c-C3H5
CH3S(O)2


 967
CH3
4-CH3-C6H4
c-C3H5
Cl


 968
CH3
4-CH3-C6H4
c-C3H5
Br


 969
CH3
4-CH3-C6H4
c-C3H5
I


 970
CH3
4-CH3-C6H4
c-C3H5
CF3


 971
CH3
4-CH3-C6H4
c-C3H5
CH3S(O)


 972
CH3
4-CH3-C6H4
c-C3H5
CH3S(O)2


 973
CH3
4-CH3O-C6H4
c-C3H5
Cl


 974
CH3
4-CH3O-C6H4
c-C3H5
Br


 975
CH3
4-CH3O-C6H4
c-C3H5
I


 976
CH3
4-CH3O-C6H4
c-C3H5
CF3


 977
CH3
4-CH3O-C6H4
c-C3H5
CH3S(O)


 978
CH3
4-CH3O-C6H4
c-C3H5
CH3S(O)2


 979
CH3
2,6-(CH3)2-C6H3
c-C3H5
Cl


 980
CH3
2,6-(CH3)2-C6H3
c-C3H5
Br


 981
CH3
2,6-(CH3)2-C6H3
c-C3H5
I


 982
CH3
2,6-(CH3)2-C6H3
c-C3H5
CF3


 983
CH3
2,6-(CH3)2-C6H3
c-C3H5
CH3S(O)


 984
CH3
2,6-(CH3)2-C6H3
c-C3H5
CH3S(O)2


 985
CH3
(CH3)3C
CHF2CH2
Cl


 986
CH3
(CH3)3C
CHF2CH2
Br


 987
CH3
(CH3)3C
CHF2CH2
I


 988
CH3
(CH3)3C
CHF2CH2
CF3


 989
CH3
(CH3)3C
CHF2CH2
CH3S(O)


 990
CH3
(CH3)3C
CHF2CH2
CH3S(O)2


 991
CH3
CHF2CH2
CHF2CH2
Cl


 992
CH3
CHF2CH2
CHF2CH2
Br


 993
CH3
CHF2CH2
CHF2CH2
I


 994
CH3
CHF2CH2
CHF2CH2
CF3


 995
CH3
CHF2CH2
CHF2CH2
CH3S(O)


 996
CH3
CHF2CH2
CHF2CH2
CH3S(O)2


 997
CH3
CF3CH2
CHF2CH2
Cl


 998
CH3
CF3CH2
CHF2CH2
Br


 999
CH3
CF3CH2
CHF2CH2
I


1000
CH3
CF3CH2
CHF2CH2
CF3


1001
CH3
CF3CH2
CHF2CH2
CH3S(O)


1002
CH3
CF3CH2
CHF2CH2
CH3S(O)2


1003
CH3
CH3O
CHF2CH2
Cl


1004
CH3
CH3O
CHF2CH2
Br


1005
CH3
CH3O
CHF2CH2
I


1006
CH3
CH3O
CHF2CH2
CF3


1007
CH3
CH3O
CHF2CH2
CH3S(O)


1008
CH3
CH3O
CHF2CH2
CH3S(O)2


1009
CH3
C6H5
CHF2CH2
Cl


1010
CH3
C6H5
CHF2CH2
Br


1011
CH3
C6H5
CHF2CH2
I


1012
CH3
C6H5
CHF2CH2
CF3


1013
CH3
C6H5
CHF2CH2
CH3S(O)


1014
CH3
C6H5
CHF2CH2
CH3S(O)2


1015
CH3
4-Cl-C6H4
CHF2CH2
Cl


1016
CH3
4-Cl-C6H4
CHF2CH2
Br


1017
CH3
4-Cl-C6H4
CHF2CH2
I


1018
CH3
4-Cl-C6H4
CHF2CH2
CF3


1019
CH3
4-Cl-C6H4
CHF2CH2
CH3S(O)


1020
CH3
4-Cl-C6H4
CHF2CH2
CH3S(O)2


1021
CH3
4-CH3-C6H4
CHF2CH2
Cl


1022
CH3
4-CH3-C6H4
CHF2CH2
Br


1023
CH3
4-CH3-C6H4
CHF2CH2
I


1024
CH3
4-CH3-C6H4
CHF2CH2
CF3


1025
CH3
4-CH3-C6H4
CHF2CH2
CH3S(O)


1026
CH3
4-CH3-C6H4
CHF2CH2
CH3S(O)2


1027
CH3
4-CH3O-C6H4
CHF2CH2
Cl


1028
CH3
4-CH3O-C6H4
CHF2CH2
Br


1029
CH3
4-CH3O-C6H4
CHF2CH2
I


1030
CH3
4-CH3O-C6H4
CHF2CH2
CF3


1031
CH3
4-CH3O-C6H4
CHF2CH2
CH3S(O)


1032
CH3
4-CH3O-C6H4
CHF2CH2
CH3S(O)2


1033
CH3
2,6-(CH3)2-C6H3
CHF2CH2
Cl


1034
CH3
2,6-(CH3)2-C6H3
CHF2CH2
Br


1035
CH3
2,6-(CH3)2-C6H3
CHF2CH2
I


1036
CH3
2,6-(CH3)2-C6H3
CHF2CH2
CF3


1037
CH3
2,6-(CH3)2-C6H3
CHF2CH2
CH3S(O)


1038
CH3
2,6-(CH3)2-C6H3
CHF2CH2
CH3S(O)2


1039
CH3
(CH3)3C
CF3CH2
Cl


1040
CH3
(CH3)3C
CF3CH2
Br


1041
CH3
(CH3)3C
CF3CH2
I


1042
CH3
(CH3)3C
CF3CH2
CF3


1043
CH3
(CH3)3C
CF3CH2
CH3S(O)


1044
CH3
(CH3)3C
CF3CH2
CH3S(O)2


1045
CH3
CF3CH2
CF3CH2
Cl


1046
CH3
CF3CH2
CF3CH2
Br


1047
CH3
CF3CH2
CF3CH2
I


1048
CH3
CF3CH2
CF3CH2
CF3


1049
CH3
CF3CH2
CF3CH2
CH3S(O)


1050
CH3
CF3CH2
CF3CH2
CH3S(O)2


1051
CH3
CH3O
CF3CH2
Cl


1052
CH3
CH3O
CF3CH2
Br


1053
CH3
CH3O
CF3CH2
I


1054
CH3
CH3O
CF3CH2
CF3


1055
CH3
CH3O
CF3CH2
CH3S(O)


1056
CH3
CH3O
CF3CH2
CH3S(O)2


1057
CH3
C6H5
CF3CH2
Cl


1058
CH3
C6H5
CF3CH2
Br


1059
CH3
C6H5
CF3CH2
I


1060
CH3
C6H5
CF3CH2
CF3


1061
CH3
C6H5
CF3CH2
CH3S(O)


1062
CH3
C6H5
CF3CH2
CH3S(O)2


1063
CH3
4-Cl-C6H4
CF3CH2
Cl


1064
CH3
4-Cl-C6H4
CF3CH2
Br


1065
CH3
4-Cl-C6H4
CF3CH2
I


1066
CH3
4-Cl-C6H4
CF3CH2
CF3


1067
CH3
4-Cl-C6H4
CF3CH2
CH3S(O)


1068
CH3
4-Cl-C6H4
CF3CH2
CH3S(O)2


1069
CH3
4-CH3-C6H4
CF3CH2
Cl


1070
CH3
4-CH3-C6H4
CF3CH2
Br


1071
CH3
4-CH3-C6H4
CF3CH2
I


1072
CH3
4-CH3-C6H4
CF3CH2
CF3


1073
CH3
4-CH3-C6H4
CF3CH2
CH3S(O)


1074
CH3
4-CH3-C6H4
CF3CH2
CH3S(O)2


1075
CH3
4-CH3O-C6H4
CF3CH2
Cl


1076
CH3
4-CH3O-C6H4
CF3CH2
Br


1077
CH3
4-CH3O-C6H4
CF3CH2
I


1078
CH3
4-CH3O-C6H4
CF3CH2
CF3


1079
CH3
4-CH3O-C6H4
CF3CH2
CH3S(O)


1080
CH3
4-CH3O-C6H4
CF3CH2
CH3S(O)2


1081
CH3
2,6-(CH3)2-C6H3
CF3CH2
Cl


1082
CH3
2,6-(CH3)2-C6H3
CF3CH2
Br


1083
CH3
2,6-(CH3)2-C6H3
CF3CH2
I


1084
CH3
2,6-(CH3)2-C6H3
CF3CH2
CF3


1085
CH3
2,6-(CH3)2-C6H3
CF3CH2
CH3S(O)


1086
CH3
2,6-(CH3)2-C6H3
CF3CH2
CH3S(O)2













1087
CH3


embedded image


Cl





1088
CH3


embedded image


Br





1089
CH3


embedded image


I





1090
CH3


embedded image


CF3





1091
CH3


embedded image


CH3S(O)





1092
CH3


embedded image


CH3S(O)2





1093
CH3


embedded image


Cl





1094
CH3


embedded image


Br





1095
CH3


embedded image


I





1096
CH3


embedded image


CF3





1097
CH3


embedded image


CH3S(O)





1098
CH3


embedded image


CH3S(O)2





1099
CH3


embedded image


Cl





1100
CH3


embedded image


Br





1101
CH3


embedded image


I





1102
CH3


embedded image


CF3





1103
CH3


embedded image


CH3S(O)





1104
CH3


embedded image


CH3S(O)2














1105
OCH3
CH3
H
Cl


1106
OCH3
CH3
H
Br


1107
OCH3
CH3
H
I


1108
OCH3
CH3
H
CF3


1109
OCH3
CH3
H
CH3S(O)


1110
OCH3
CH3
H
CH3S(O)2


1111
OCH3
C2H5
H
Cl


1112
OCH3
C2H5
H
Br


1113
OCH3
C2H5
H
I


1114
OCH3
C2H5
H
CF3


1115
OCH3
C2H5
H
CH3S(O)


1116
OCH3
C2H5
H
CH3S(O)2


1117
OCH3
CH3CH2CH2
H
Cl


1118
OCH3
CH3CH2CH2
H
Br


1119
OCH3
CH3CH2CH2
H
I


1120
OCH3
CH3CH2CH2
H
CF3


1121
OCH3
CH3CH2CH2
H
CH3S(O)


1122
OCH3
CH3CH2CH2
H
CH3S(O)2


1123
OCH3
(CH3)2CH
H
Cl


1124
OCH3
(CH3)2CH
H
Br


1125
OCH3
(CH3)2CH
H
I


1126
OCH3
(CH3)2CH
H
CF3


1127
OCH3
(CH3)2CH
H
CH3S(O)


1128
OCH3
(CH3)2CH
H
CH3S(O)2


1129
OCH3
(CH3)3C
H
Cl


1130
OCH3
(CH3)3C
H
Br


1131
OCH3
(CH3)3C
H
I


1132
OCH3
(CH3)3C
H
CF3


1133
OCH3
(CH3)3C
H
CH3S(O)


1134
OCH3
(CH3)3C
H
CH3S(O)2


1135
OCH3
c-C3H5
H
Cl


1136
OCH3
c-C3H5
H
Br


1137
OCH3
c-C3H5
H
I


1138
OCH3
c-C3H5
H
CF3


1139
OCH3
c-C3H5
H
CH3S(O)


1140
OCH3
c-C3H5
H
CH3S(O)2


1141
OCH3
CHF2CH2
H
Cl


1142
OCH3
CHF2CH2
H
Br


1143
OCH3
CHF2CH2
H
I


1144
OCH3
CHF2CH2
H
CF3


1145
OCH3
CHF2CH2
H
CH3S(O)


1146
OCH3
CHF2CH2
H
CH3S(O)2


1147
OCH3
CF3CH2
H
Cl


1148
OCH3
CF3CH2
H
Br


1149
OCH3
CF3CH2
H
I


1150
OCH3
CF3CH2
H
CF3


1151
OCH3
CF3CH2
H
CH3S(O)


1152
OCH3
CF3CH2
H
CH3S(O)2


1153
OCH3
CH3O
H
Cl


1154
OCH3
CH3O
H
Br


1155
OCH3
CH3O
H
I


1156
OCH3
CH3O
H
CF3


1157
OCH3
CH3O
H
CH3S(O)


1158
OCH3
CH3O
H
CH3S(O)2


1159
OCH3
C6H5
H
Cl


1160
OCH3
C6H5
H
Br


1161
OCH3
C6H5
H
I


1162
OCH3
C6H5
H
CF3


1163
OCH3
C6H5
H
CH3S(O)


1164
OCH3
C6H5
H
CH3S(O)2


1165
OCH3
4-Cl-C6H4
H
Cl


1166
OCH3
4-Cl-C6H4
H
Br


1167
OCH3
4-Cl-C6H4
H
I


1168
OCH3
4-Cl-C6H4
H
CF3


1169
OCH3
4-Cl-C6H4
H
CH3S(O)


1170
OCH3
4-Cl-C6H4
H
CH3S(O)2


1171
OCH3
4-CH3-C6H4
H
Cl


1172
OCH3
4-CH3-C6H4
H
Br


1173
OCH3
4-CH3-C6H4
H
I


1174
OCH3
4-CH3-C6H4
H
CF3


1175
OCH3
4-CH3-C6H4
H
CH3S(O)


1176
OCH3
4-CH3-C6H4
H
CH3S(O)2


1177
OCH3
4-CH3O-C6H4
H
Cl


1178
OCH3
4-CH3O-C6H4
H
Br


1179
OCH3
4-CH3O-C6H4
H
I


1180
OCH3
4-CH3O-C6H4
H
CF3


1181
OCH3
4-CH3O-C6H4
H
CH3S(O)


1182
OCH3
4-CH3O-C6H4
H
CH3S(O)2


1183
OCH3
2,6-(CH3)2-C6H3
H
Cl


1184
OCH3
2,6-(CH3)2-C6H3
H
Br


1185
OCH3
2,6-(CH3)2-C6H3
H
I


1186
OCH3
2,6-(CH3)2-C6H3
H
CF3


1187
OCH3
2,6-(CH3)2-C6H3
H
CH3S(O)


1188
OCH3
2,6-(CH3)2-C6H3
H
CH3S(O)2


1189
OCH3
CH3
CH3
Cl


1190
OCH3
CH3
CH3
Br


1191
OCH3
CH3
CH3
I


1192
OCH3
CH3
CH3
CF3


1193
OCH3
CH3
CH3
CH3S(O)


1194
OCH3
CH3
CH3
CH3S(O)2


1195
OCH3
C2H5
CH3
Cl


1196
OCH3
C2H5
CH3
Br


1197
OCH3
C2H5
CH3
I


1198
OCH3
C2H5
CH3
CF3


1199
OCH3
C2H5
CH3
CH3S(O)


1200
OCH3
C2H5
CH3
CH3S(O)2


1201
OCH3
CH3CH2CH2
CH3
Cl


1202
OCH3
CH3CH2CH2
CH3
Br


1203
OCH3
CH3CH2CH2
CH3
I


1204
OCH3
CH3CH2CH2
CH3
CF3


1205
OCH3
CH3CH2CH2
CH3
CH3S(O)


1206
OCH3
CH3CH2CH2
CH3
CH3S(O)2


1207
OCH3
(CH3)2CH
CH3
Cl


1208
OCH3
(CH3)2CH
CH3
Br


1209
OCH3
(CH3)2CH
CH3
I


1210
OCH3
(CH3)2CH
CH3
CF3


1211
OCH3
(CH3)2CH
CH3
CH3S(O)


1212
OCH3
(CH3)2CH
CH3
CH3S(O)2


1213
OCH3
(CH3)3C
CH3
Cl


1214
OCH3
(CH3)3C
CH3
Br


1215
OCH3
(CH3)3C
CH3
I


1216
OCH3
(CH3)3C
CH3
CF3


1217
OCH3
(CH3)3C
CH3
CH3S(O)


1218
OCH3
(CH3)3C
CH3
CH3S(O)2


1219
OCH3
c-C3H5
CH3
Cl


1220
OCH3
c-C3H5
CH3
Br


1221
OCH3
c-C3H5
CH3
I


1222
OCH3
c-C3H5
CH3
CF3


1223
OCH3
c-C3H5
CH3
CH3S(O)


1224
OCH3
c-C3H5
CH3
CH3S(O)2


1225
OCH3
CHF2CH2
CH3
Cl


1226
OCH3
CHF2CH2
CH3
Br


1227
OCH3
CHF2CH2
CH3
I


1228
OCH3
CHF2CH2
CH3
CF3


1229
OCH3
CHF2CH2
CH3
CH3S(O)


1230
OCH3
CHF2CH2
CH3
CH3S(O)2


1231
OCH3
CF3CH2
CH3
Cl


1232
OCH3
CF3CH2
CH3
Br


1233
OCH3
CF3CH2
CH3
I


1234
OCH3
CF3CH2
CH3
CF3


1235
OCH3
CF3CH2
CH3
CH3S(O)


1236
OCH3
CF3CH2
CH3
CH3S(O)2


1237
OCH3
CH3O
CH3
Cl


1238
OCH3
CH3O
CH3
Br


1239
OCH3
CH3O
CH3
I


1240
OCH3
CH3O
CH3
CF3


1241
OCH3
CH3O
CH3
CH3S(O)


1242
OCH3
CH3O
CH3
CH3S(O)2


1243
OCH3
C6H5
CH3
Cl


1244
OCH3
C6H5
CH3
Br


1245
OCH3
C6H5
CH3
I


1246
OCH3
C6H5
CH3
CF3


1247
OCH3
C6H5
CH3
CH3S(O)


1248
OCH3
C6H5
CH3
CH3S(O)2


1249
OCH3
4-Cl-C6H4
CH3
Cl


1250
OCH3
4-Cl-C6H4
CH3
Br


1251
OCH3
4-Cl-C6H4
CH3
I


1252
OCH3
4-Cl-C6H4
CH3
CF3


1253
OCH3
4-Cl-C6H4
CH3
CH3S(O)


1254
OCH3
4-Cl-C6H4
CH3
CH3S(O)2


1255
OCH3
4-CH3-C6H4
CH3
Cl


1256
OCH3
4-CH3-C6H4
CH3
Br


1257
OCH3
4-CH3-C6H4
CH3
I


1258
OCH3
4-CH3-C6H4
CH3
CF3


1259
OCH3
4-CH3-C6H4
CH3
CH3S(O)


1260
OCH3
4-CH3-C6H4
CH3
CH3S(O)2


1261
OCH3
4-CH3O-C6H4
CH3
Cl


1262
OCH3
4-CH3O-C6H4
CH3
Br


1263
OCH3
4-CH3O-C6H4
CH3
I


1264
OCH3
4-CH3O-C6H4
CH3
CF3


1265
OCH3
4-CH3O-C6H4
CH3
CH3S(O)


1266
OCH3
4-CH3O-C6H4
CH3
CH3S(O)2


1267
OCH3
2,6-(CH3)2-C6H3
CH3
Cl


1268
OCH3
2,6-(CH3)2-C6H3
CH3
Br


1269
OCH3
2,6-(CH3)2-C6H3
CH3
I


1270
OCH3
2,6-(CH3)2-C6H3
CH3
CF3


1271
OCH3
2,6-(CH3)2-C6H3
CH3
CH3S(O)


1272
OCH3
2,6-(CH3)2-C6H3
CH3
CH3S(O)2


1273
OCH3
C2H5
C2H5
Cl


1274
OCH3
C2H5
C2H5
Br


1275
OCH3
C2H5
C2H5
I


1276
OCH3
C2H5
C2H5
CF3


1277
OCH3
C2H5
C2H5
CH3S(O)


1278
OCH3
C2H5
C2H5
CH3S(O)2


1279
OCH3
CH3CH2CH2
C2H5
Cl


1280
OCH3
CH3CH2CH2
C2H5
Br


1281
OCH3
CH3CH2CH2
C2H5
I


1282
OCH3
CH3CH2CH2
C2H5
CF3


1283
OCH3
CH3CH2CH2
C2H5
CH3S(O)


1284
OCH3
CH3CH2CH2
C2H5
CH3S(O)2


1285
OCH3
(CH3)2CH
C2H5
Cl


1286
OCH3
(CH3)2CH
C2H5
Br


1287
OCH3
(CH3)2CH
C2H5
I


1288
OCH3
(CH3)2CH
C2H5
CF3


1289
OCH3
(CH3)2CH
C2H5
CH3S(O)


1290
OCH3
(CH3)2CH
C2H5
CH3S(O)2


1291
OCH3
(CH3)3C
C2H5
Cl


1292
OCH3
(CH3)3C
C2H5
Br


1293
OCH3
(CH3)3C
C2H5
I


1294
OCH3
(CH3)3C
C2H5
CF3


1295
OCH3
(CH3)3C
C2H5
CH3S(O)


1296
OCH3
(CH3)3C
C2H5
CH3S(O)2


1297
OCH3
c-C3H5
C2H5
Cl


1298
OCH3
c-C3H5
C2H5
Br


1299
OCH3
c-C3H5
C2H5
I


1300
OCH3
c-C3H5
C2H5
CF3


1301
OCH3
c-C3H5
C2H5
CH3S(O)


1302
OCH3
c-C3H5
C2H5
CH3S(O)2


1303
OCH3
CHF2CH2
C2H5
Cl


1304
OCH3
CHF2CH2
C2H5
Br


1305
OCH3
CHF2CH2
C2H5
I


1306
OCH3
CHF2CH2
C2H5
CF3


1307
OCH3
CHF2CH2
C2H5
CH3S(O)


1308
OCH3
CHF2CH2
C2H5
CH3S(O)2


1309
OCH3
CF3CH2
C2H5
Cl


1310
OCH3
CF3CH2
C2H5
Br


1311
OCH3
CF3CH2
C2H5
I


1312
OCH3
CF3CH2
C2H5
CF3


1313
OCH3
CF3CH2
C2H5
CH3S(O)


1314
OCH3
CF3CH2
C2H5
CH3S(O)2


1315
OCH3
CH3O
C2H5
Cl


1316
OCH3
CH3O
C2H5
Br


1317
OCH3
CH3O
C2H5
I


1318
OCH3
CH3O
C2H5
CF3


1319
OCH3
CH3O
C2H5
CH3S(O)


1320
OCH3
CH3O
C2H5
CH3S(O)2


1321
OCH3
C6H5
C2H5
Cl


1322
OCH3
C6H5
C2H5
Br


1323
OCH3
C6H5
C2H5
I


1324
OCH3
C6H5
C2H5
CF3


1325
OCH3
C6H5
C2H5
CH3S(O)


1326
OCH3
C6H5
C2H5
CH3S(O)2


1327
OCH3
4-Cl-C6H4
C2H5
Cl


1328
OCH3
4-Cl-C6H4
C2H5
Br


1329
OCH3
4-Cl-C6H4
C2H5
I


1330
OCH3
4-Cl-C6H4
C2H5
CF3


1331
OCH3
4-Cl-C6H4
C2H5
CH3S(O)


1332
OCH3
4-Cl-C6H4
C2H5
CH3S(O)2


1333
OCH3
4-CH3-C6H4
C2H5
Cl


1334
OCH3
4-CH3-C6H4
C2H5
Br


1335
OCH3
4-CH3-C6H4
C2H5
I


1336
OCH3
4-CH3-C6H4
C2H5
CF3


1337
OCH3
4-CH3-C6H4
C2H5
CH3S(O)


1338
OCH3
4-CH3-C6H4
C2H5
CH3S(O)2


1339
OCH3
4-CH3O-C6H4
C2H5
Cl


1340
OCH3
4-CH3O-C6H4
C2H5
Br


1341
OCH3
4-CH3O-C6H4
C2H5
I


1342
OCH3
4-CH3O-C6H4
C2H5
CF3


1343
OCH3
4-CH3O-C6H4
C2H5
CH3S(O)


1344
OCH3
4-CH3O-C6H4
C2H5
CH3S(O)2


1345
OCH3
2,6-(CH3)2-C6H3
C2H5
Cl


1346
OCH3
2,6-(CH3)2-C6H3
C2H5
Br


1347
OCH3
2,6-(CH3)2-C6H3
C2H5
I


1348
OCH3
2,6-(CH3)2-C6H3
C2H5
CF3


1349
OCH3
2,6-(CH3)2-C6H3
C2H5
CH3S(O)


1350
OCH3
2,6-(CH3)2-C6H3
C2H5
CH3S(O)2


1351
OCH3
CH3CH2CH2
CH3CH2CH2
Cl


1352
OCH3
CH3CH2CH2
CH3CH2CH2
Br


1353
OCH3
CH3CH2CH2
CH3CH2CH2
I


1354
OCH3
CH3CH2CH2
CH3CH2CH2
CF3


1355
OCH3
CH3CH2CH2
CH3CH2CH2
CH3S(O)


1356
OCH3
CH3CH2CH2
CH3CH2CH2
CH3S(O)2


1357
OCH3
(CH3)2CH
CH3CH2CH2
Cl


1358
OCH3
(CH3)2CH
CH3CH2CH2
Br


1359
OCH3
(CH3)2CH
CH3CH2CH2
I


1360
OCH3
(CH3)2CH
CH3CH2CH2
CF3


1361
OCH3
(CH3)2CH
CH3CH2CH2
CH3S(O)


1362
OCH3
(CH3)2CH
CH3CH2CH2
CH3S(O)2


1363
OCH3
(CH3)3C
CH3CH2CH2
Cl


1364
OCH3
(CH3)3C
CH3CH2CH2
Br


1365
OCH3
(CH3)3C
CH3CH2CH2
I


1366
OCH3
(CH3)3C
CH3CH2CH2
CF3


1367
OCH3
(CH3)3C
CH3CH2CH2
CH3S(O)


1368
OCH3
(CH3)3C
CH3CH2CH2
CH3S(O)2


1369
OCH3
c-C3H5
CH3CH2CH2
Cl


1370
OCH3
c-C3H5
CH3CH2CH2
Br


1371
OCH3
c-C3H5
CH3CH2CH2
I


1372
OCH3
c-C3H5
CH3CH2CH2
CF3


1373
OCH3
c-C3H5
CH3CH2CH2
CH3S(O)


1374
OCH3
c-C3H5
CH3CH2CH2
CH3S(O)2


1375
OCH3
CHF2CH2
CH3CH2CH2
Cl


1376
OCH3
CHF2CH2
CH3CH2CH2
Br


1377
OCH3
CHF2CH2
CH3CH2CH2
I


1378
OCH3
CHF2CH2
CH3CH2CH2
CF3


1379
OCH3
CHF2CH2
CH3CH2CH2
CH3S(O)


1380
OCH3
CHF2CH2
CH3CH2CH2
CH3S(O)2


1381
OCH3
CF3CH2
CH3CH2CH2
Cl


1382
OCH3
CF3CH2
CH3CH2CH2
Br


1383
OCH3
CF3CH2
CH3CH2CH2
I


1384
OCH3
CF3CH2
CH3CH2CH2
CF3


1385
OCH3
CF3CH2
CH3CH2CH2
CH3S(O)


1386
OCH3
CF3CH2
CH3CH2CH2
CH3S(O)2


1387
OCH3
CH3O
CH3CH2CH2
Cl


1388
OCH3
CH3O
CH3CH2CH2
Br


1389
OCH3
CH3O
CH3CH2CH2
I


1390
OCH3
CH3O
CH3CH2CH2
CF3


1391
OCH3
CH3O
CH3CH2CH2
CH3S(O)


1392
OCH3
CH3O
CH3CH2CH2
CH3S(O)2


1393
OCH3
C6H5
CH3CH2CH2
Cl


1394
OCH3
C6H5
CH3CH2CH2
Br


1395
OCH3
C6H5
CH3CH2CH2
I


1396
OCH3
C6H5
CH3CH2CH2
CF3


1397
OCH3
C6H5
CH3CH2CH2
CH3S(O)


1398
OCH3
C6H5
CH3CH2CH2
CH3S(O)2


1399
OCH3
4-Cl-C6H4
CH3CH2CH2
Cl


1400
OCH3
4-Cl-C6H4
CH3CH2CH2
Br


1401
OCH3
4-Cl-C6H4
CH3CH2CH2
I


1402
OCH3
4-Cl-C6H4
CH3CH2CH2
CF3


1403
OCH3
4-Cl-C6H4
CH3CH2CH2
CH3S(O)


1404
OCH3
4-Cl-C6H4
CH3CH2CH2
CH3S(O)2


1405
OCH3
4-CH3-C6H4
CH3CH2CH2
Cl


1406
OCH3
4-CH3-C6H4
CH3CH2CH2
Br


1407
OCH3
4-CH3-C6H4
CH3CH2CH2
I


1408
OCH3
4-CH3-C6H4
CH3CH2CH2
CF3


1409
OCH3
4-CH3-C6H4
CH3CH2CH2
CH3S(O)


1410
OCH3
4-CH3-C6H4
CH3CH2CH2
CH3S(O)2


1411
OCH3
4-CH3O-C6H4
CH3CH2CH2
Cl


1412
OCH3
4-CH3O-C6H4
CH3CH2CH2
Br


1413
OCH3
4-CH3O-C6H4
CH3CH2CH2
I


1414
OCH3
4-CH3O-C6H4
CH3CH2CH2
CF3


1415
OCH3
4-CH3O-C6H4
CH3CH2CH2
CH3S(O)


1416
OCH3
4-CH3O-C6H4
CH3CH2CH2
CH3S(O)2


1417
OCH3
2,6-(CH3)2-C6H3
CH3CH2CH2
Cl


1418
OCH3
2,6-(CH3)2-C6H3
CH3CH2CH2
Br


1419
OCH3
2,6-(CH3)2-C6H3
CH3CH2CH2
I


1420
OCH3
2,6-(CH3)2-C6H3
CH3CH2CH2
CF3


1421
OCH3
2,6-(CH3)2-C6H3
CH3CH2CH2
CH3S(O)


1422
OCH3
2,6-(CH3)2-C6H3
CH3CH2CH2
CH3S(O)2


1423
OCH3
(CH3)2CH
(CH3)2CH
Cl


1424
OCH3
(CH3)2CH
(CH3)2CH
Br


1425
OCH3
(CH3)2CH
(CH3)2CH
I


1426
OCH3
(CH3)2CH
(CH3)2CH
CF3


1427
OCH3
(CH3)2CH
(CH3)2CH
CH3S(O)


1428
OCH3
(CH3)2CH
(CH3)2CH
CH3S(O)2


1429
OCH3
c-C3H5
(CH3)2CH
Cl


1430
OCH3
c-C3H5
(CH3)2CH
Br


1431
OCH3
c-C3H5
(CH3)2CH
I


1432
OCH3
c-C3H5
(CH3)2CH
CF3


1433
OCH3
c-C3H5
(CH3)2CH
CH3S(O)


1434
OCH3
c-C3H5
(CH3)2CH
CH3S(O)2


1435
OCH3
CHF2CH2
(CH3)2CH
Cl


1436
OCH3
CHF2CH2
(CH3)2CH
Br


1437
OCH3
CHF2CH2
(CH3)2CH
I


1438
OCH3
CHF2CH2
(CH3)2CH
CF3


1439
OCH3
CHF2CH2
(CH3)2CH
CH3S(O)


1440
OCH3
CHF2CH2
(CH3)2CH
CH3S(O)2


1441
OCH3
CF3CH2
(CH3)2CH
Cl


1442
OCH3
CF3CH2
(CH3)2CH
Br


1443
OCH3
CF3CH2
(CH3)2CH
I


1444
OCH3
CF3CH2
(CH3)2CH
CF3


1445
OCH3
CF3CH2
(CH3)2CH
CH3S(O)


1446
OCH3
CF3CH2
(CH3)2CH
CH3S(O)2


1447
OCH3
CH3O
(CH3)2CH
Cl


1448
OCH3
CH3O
(CH3)2CH
Br


1449
OCH3
CH3O
(CH3)2CH
I


1450
OCH3
CH3O
(CH3)2CH
CF3


1451
OCH3
CH3O
(CH3)2CH
CH3S(O)


1452
OCH3
CH3O
(CH3)2CH
CH3S(O)2


1453
OCH3
C6H5
(CH3)2CH
Cl


1454
OCH3
C6H5
(CH3)2CH
Br


1455
OCH3
C6H5
(CH3)2CH
I


1456
OCH3
C6H5
(CH3)2CH
CF3


1457
OCH3
C6H5
(CH3)2CH
CH3S(O)


1458
OCH3
C6H5
(CH3)2CH
CH3S(O)2


1459
OCH3
4-Cl-C6H4
(CH3)2CH
Cl


1460
OCH3
4-Cl-C6H4
(CH3)2CH
Br


1461
OCH3
4-Cl-C6H4
(CH3)2CH
I


1462
OCH3
4-Cl-C6H4
(CH3)2CH
CF3


1463
OCH3
4-Cl-C6H4
(CH3)2CH
CH3S(O)


1464
OCH3
4-Cl-C6H4
(CH3)2CH
CH3S(O)2


1465
OCH3
4-CH3-C6H4
(CH3)2CH
Cl


1466
OCH3
4-CH3-C6H4
(CH3)2CH
Br


1467
OCH3
4-CH3-C6H4
(CH3)2CH
I


1468
OCH3
4-CH3-C6H4
(CH3)2CH
CF3


1469
OCH3
4-CH3-C6H4
(CH3)2CH
CH3S(O)


1470
OCH3
4-CH3-C6H4
(CH3)2CH
CH3S(O)2


1471
OCH3
4-CH3O-C6H4
(CH3)2CH
Cl


1472
OCH3
4-CH3O-C6H4
(CH3)2CH
Br


1473
OCH3
4-CH3O-C6H4
(CH3)2CH
I


1474
OCH3
4-CH3O-C6H4
(CH3)2CH
CF3


1475
OCH3
4-CH3O-C6H4
(CH3)2CH
CH3S(O)


1476
OCH3
4-CH3O-C6H4
(CH3)2CH
CH3S(O)2


1477
OCH3
2,6-(CH3)2-C6H3
(CH3)2CH
Cl


1478
OCH3
2,6-(CH3)2-C6H3
(CH3)2CH
Br


1479
OCH3
2,6-(CH3)2-C6H3
(CH3)2CH
I


1480
OCH3
2,6-(CH3)2-C6H3
(CH3)2CH
CF3


1481
OCH3
2,6-(CH3)2-C6H3
(CH3)2CH
CH3S(O)


1482
OCH3
2,6-(CH3)2-C6H3
(CH3)2CH
CH3S(O)2


1483
OCH3
c-C3H5
c-C3H5
Cl


1484
OCH3
c-C3H5
c-C3H5
Br


1485
OCH3
c-C3H5
c-C3H5
I


1486
OCH3
c-C3H5
c-C3H5
CF3


1487
OCH3
c-C3H5
c-C3H5
CH3S(O)


1488
OCH3
c-C3H5
c-C3H5
CH3S(O)2


1489
OCH3
CHF2CH2
c-C3H5
Cl


1490
OCH3
CHF2CH2
c-C3H5
Br


1491
OCH3
CHF2CH2
c-C3H5
I


1492
OCH3
CHF2CH2
c-C3H5
CF3


1493
OCH3
CHF2CH2
c-C3H5
CH3S(O)


1494
OCH3
CHF2CH2
c-C3H5
CH3S(O)2


1495
OCH3
CF3CH2
c-C3H5
Cl


1496
OCH3
CF3CH2
c-C3H5
Br


1497
OCH3
CF3CH2
c-C3H5
I


1498
OCH3
CF3CH2
c-C3H5
CF3


1499
OCH3
CF3CH2
c-C3H5
CH3S(O)


1500
OCH3
CF3CH2
c-C3H5
CH3S(O)2


1501
OCH3
CH3O
c-C3H5
Cl


1502
OCH3
CH3O
c-C3H5
Br


1503
OCH3
CH3O
c-C3H5
I


1504
OCH3
CH3O
c-C3H5
CF3


1505
OCH3
CH3O
c-C3H5
CH3S(O)


1506
OCH3
CH3O
c-C3H5
CH3S(O)2


1507
OCH3
C6H5
c-C3H5
Cl


1508
OCH3
C6H5
c-C3H5
Br


1509
OCH3
C6H5
c-C3H5
I


1510
OCH3
C6H5
c-C3H5
CF3


1511
OCH3
C6H5
c-C3H5
CH3S(O)


1512
OCH3
C6H5
c-C3H5
CH3S(O)2


1513
OCH3
4-Cl-C6H4
c-C3H5
Cl


1514
OCH3
4-Cl-C6H4
c-C3H5
Br


1515
OCH3
4-Cl-C6H4
c-C3H5
I


1516
OCH3
4-Cl-C6H4
c-C3H5
CF3


1517
OCH3
4-Cl-C6H4
c-C3H5
CH3S(O)


1518
OCH3
4-Cl-C6H4
c-C3H5
CH3S(O)2


1519
OCH3
4-CH3-C6H4
c-C3H5
Cl


1520
OCH3
4-CH3-C6H4
c-C3H5
Br


1521
OCH3
4-CH3-C6H4
c-C3H5
I


1522
OCH3
4-CH3-C6H4
c-C3H5
CF3


1523
OCH3
4-CH3-C6H4
c-C3H5
CH3S(O)


1524
OCH3
4-CH3-C6H4
c-C3H5
CH3S(O)2


1525
OCH3
4-CH3O-C6H4
c-C3H5
Cl


1526
OCH3
4-CH3O-C6H4
c-C3H5
Br


1527
OCH3
4-CH3O-C6H4
c-C3H5
I


1528
OCH3
4-CH3O-C6H4
c-C3H5
CF3


1529
OCH3
4-CH3O-C6H4
c-C3H5
CH3S(O)


1530
OCH3
4-CH3O-C6H4
c-C3H5
CH3S(O)2


1531
OCH3
2,6-(CH3)2-C6H3
c-C3H5
Cl


1532
OCH3
2,6-(CH3)2-C6H3
c-C3H5
Br


1533
OCH3
2,6-(CH3)2-C6H3
c-C3H5
I


1534
OCH3
2,6-(CH3)2-C6H3
c-C3H5
CF3


1535
OCH3
2,6-(CH3)2-C6H3
c-C3H5
CH3S(O)


1536
OCH3
2,6-(CH3)2-C6H3
c-C3H5
CH3S(O)2


1537
OCH3
(CH3)3C
CHF2CH2
Cl


1538
OCH3
(CH3)3C
CHF2CH2
Br


1539
OCH3
(CH3)3C
CHF2CH2
I


1540
OCH3
(CH3)3C
CHF2CH2
CF3


1541
OCH3
(CH3)3C
CHF2CH2
CH3S(O)


1542
OCH3
(CH3)3C
CHF2CH2
CH3S(O)2


1543
OCH3
CHF2CH2
CHF2CH2
Cl


1544
OCH3
CHF2CH2
CHF2CH2
Br


1545
OCH3
CHF2CH2
CHF2CH2
I


1546
OCH3
CHF2CH2
CHF2CH2
CF3


1547
OCH3
CHF2CH2
CHF2CH2
CH3S(O)


1548
OCH3
CHF2CH2
CHF2CH2
CH3S(O)2


1549
OCH3
CF3CH2
CHF2CH2
Cl


1550
OCH3
CF3CH2
CHF2CH2
Br


1551
OCH3
CF3CH2
CHF2CH2
I


1552
OCH3
CF3CH2
CHF2CH2
CF3


1553
OCH3
CF3CH2
CHF2CH2
CH3S(O)


1554
OCH3
CF3CH2
CHF2CH2
CH3S(O)2


1555
OCH3
CH3O
CHF2CH2
Cl


1556
OCH3
CH3O
CHF2CH2
Br


1557
OCH3
CH3O
CHF2CH2
I


1558
OCH3
CH3O
CHF2CH2
CF3


1559
OCH3
CH3O
CHF2CH2
CH3S(O)


1560
OCH3
CH3O
CHF2CH2
CH3S(O)2


1561
OCH3
C6H5
CHF2CH2
Cl


1562
OCH3
C6H5
CHF2CH2
Br


1563
OCH3
C6H5
CHF2CH2
I


1564
OCH3
C6H5
CHF2CH2
CF3


1565
OCH3
C6H5
CHF2CH2
CH3S(O)


1566
OCH3
C6H5
CHF2CH2
CH3S(O)2


1567
OCH3
4-Cl-C6H4
CHF2CH2
Cl


1568
OCH3
4-Cl-C6H4
CHF2CH2
Br


1569
OCH3
4-Cl-C6H4
CHF2CH2
I


1570
OCH3
4-Cl-C6H4
CHF2CH2
CF3


1571
OCH3
4-Cl-C6H4
CHF2CH2
CH3S(O)


1572
OCH3
4-Cl-C6H4
CHF2CH2
CH3S(O)2


1573
OCH3
4-CH3-C6H4
CHF2CH2
Cl


1574
OCH3
4-CH3-C6H4
CHF2CH2
Br


1575
OCH3
4-CH3-C6H4
CHF2CH2
I


1576
OCH3
4-CH3-C6H4
CHF2CH2
CF3


1577
OCH3
4-CH3-C6H4
CHF2CH2
CH3S(O)


1578
OCH3
4-CH3-C6H4
CHF2CH2
CH3S(O)2


1579
OCH3
4-CH3O-C6H4
CHF2CH2
Cl


1580
OCH3
4-CH3O-C6H4
CHF2CH2
Br


1581
OCH3
4-CH3O-C6H4
CHF2CH2
I


1582
OCH3
4-CH3O-C6H4
CHF2CH2
CF3


1583
OCH3
4-CH3O-C6H4
CHF2CH2
CH3S(O)


1584
OCH3
4-CH3O-C6H4
CHF2CH2
CH3S(O)2


1585
OCH3
2,6-(CH3)2-C6H3
CHF2CH2
Cl


1586
OCH3
2,6-(CH3)2-C6H3
CHF2CH2
Br


1587
OCH3
2,6-(CH3)2-C6H3
CHF2CH2
I


1588
OCH3
2,6-(CH3)2-C6H3
CHF2CH2
CF3


1589
OCH3
2,6-(CH3)2-C6H3
CHF2CH2
CH3S(O)


1590
OCH3
2,6-(CH3)2-C6H3
CHF2CH2
CH3S(O)2


1591
OCH3
(CH3)3C
CF3CH2
Cl


1592
OCH3
(CH3)3C
CF3CH2
Br


1593
OCH3
(CH3)3C
CF3CH2
I


1594
OCH3
(CH3)3C
CF3CH2
CF3


1595
OCH3
(CH3)3C
CF3CH2
CH3S(O)


1596
OCH3
(CH3)3C
CF3CH2
CH3S(O)2


1597
OCH3
CF3CH2
CF3CH2
Cl


1598
OCH3
CF3CH2
CF3CH2
Br


1599
OCH3
CF3CH2
CF3CH2
I


1600
OCH3
CF3CH2
CF3CH2
CF3


1601
OCH3
CF3CH2
CF3CH2
CH3S(O)


1602
OCH3
CF3CH2
CF3CH2
CH3S(O)2


1603
OCH3
CH3O
CF3CH2
Cl


1604
OCH3
CH3O
CF3CH2
Br


1605
OCH3
CH3O
CF3CH2
I


1606
OCH3
CH3O
CF3CH2
CF3


1607
OCH3
CH3O
CF3CH2
CH3S(O)


1608
OCH3
CH3O
CF3CH2
CH3S(O)2


1609
OCH3
C6H5
CF3CH2
Cl


1610
OCH3
C6H5
CF3CH2
Br


1611
OCH3
C6H5
CF3CH2
I


1612
OCH3
C6H5
CF3CH2
CF3


1613
OCH3
C6H5
CF3CH2
CH3S(O)


1614
OCH3
C6H5
CF3CH2
CH3S(O)2


1615
OCH3
4-Cl-C6H4
CF3CH2
Cl


1616
OCH3
4-Cl-C6H4
CF3CH2
Br


1617
OCH3
4-Cl-C6H4
CF3CH2
I


1618
OCH3
4-Cl-C6H4
CF3CH2
CF3


1619
OCH3
4-Cl-C6H4
CF3CH2
CH3S(O)


1620
OCH3
4-Cl-C6H4
CF3CH2
CH3S(O)2


1621
OCH3
4-CH3-C6H4
CF3CH2
Cl


1622
OCH3
4-CH3-C6H4
CF3CH2
Br


1623
OCH3
4-CH3-C6H4
CF3CH2
I


1624
OCH3
4-CH3-C6H4
CF3CH2
CF3


1625
OCH3
4-CH3-C6H4
CF3CH2
CH3S(O)


1626
OCH3
4-CH3-C6H4
CF3CH2
CH3S(O)2


1627
OCH3
4-CH3O-C6H4
CF3CH2
Cl


1628
OCH3
4-CH3O-C6H4
CF3CH2
Br


1629
OCH3
4-CH3O-C6H4
CF3CH2
I


1630
OCH3
4-CH3O-C6H4
CF3CH2
CF3


1631
OCH3
4-CH3O-C6H4
CF3CH2
CH3S(O)


1632
OCH3
4-CH3O-C6H4
CF3CH2
CH3S(O)2


1633
OCH3
2,6-(CH3)2-C6H3
CF3CH2
Cl


1634
OCH3
2,6-(CH3)2-C6H3
CF3CH2
Br


1635
OCH3
2,6-(CH3)2-C6H3
CF3CH2
I


1636
OCH3
2,6-(CH3)2-C6H3
CF3CH2
CF3


1637
OCH3
2,6-(CH3)2-C6H3
CF3CH2
CH3S(O)


1638
OCH3
2,6-(CH3)2-C6H3
CF3CH2
CH3S(O)2













1639
OCH3


embedded image


Cl





1640
OCH3


embedded image


Br





1641
OCH3


embedded image


I





1642
OCH3


embedded image


CF3





1643
OCH3


embedded image


CH3S(O)





1644
OCH3


embedded image


CH3S(O)2





1645
OCH3


embedded image


Cl





1646
OCH3


embedded image


Br





1647
OCH3


embedded image


I





1648
OCH3


embedded image


CF3





1649
OCH3


embedded image


CH3S(O)





1650
OCH3


embedded image


CH3S(O)2





1651
OCH3


embedded image


Cl





1652
OCH3


embedded image


Br





1653
OCH3


embedded image


I





1654
OCH3


embedded image


CF3





1655
OCH3


embedded image


CH3S(O)





1656
OCH3


embedded image


CH3S(O)2









In table A, the following abbreviations are used:

    • c-C3H5 cyclopropyl;
    • C6H5 phenyl
    • 4-Cl—C6H4 4-chlorophenyl
    • 4-CH3—C6H4 4-methylphenyl
    • 4-CH3O—C6H4 4-methoxyphenyl
    • 2,6-(CH3)2—C6H3 2,6-dimethylphenyl


In a specific embodiment, the compounds I are selected from the compounds of the examples, the N-oxides thereof and the agriculturally acceptable salts thereof.


The compounds of formula I can be prepared by standard methods of organic chemistry, e.g. by the methods described in the schemes below. The substituents, variables and indices used in the schemes are as defined above for the compounds of formula I, if not specified otherwise.


The compounds of the formula I, where R2c is H can be prepared from the corresponding benzamides of the formula II, which comprises reacting the compound of formula II with thiophosgene (III) to obtain an isothiocyanate of the formula IV. Subsequent reaction of (IV) with ammonia or an amine of the formula V yields the compound of formula (I), where R2c is H. The method is depicted in the following scheme 1.




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The reaction of the compound of the formula II with thiophosgene Ill or thiophosgene equivalent and the secondary amine of formula V can be performed by analogy to the preparation of mixed thioureas by reaction of two different amine with thiiophosgene or thiophosgene equivalent. Usually, the compound of the formula II is firstly reacted with thiophosgene to obtain the isothiocyanate (IV) as an intermediate compound, which is subsequently reacted with the secondary amine of the formula IV. The isothiocyanate of formula IV may be isolated from the reaction mixture. For economical reasons, the isothiocyanate (IV) is usually not isolated but the reaction mixture obtained from the reaction of the compound (II) with the thiophosgene or thiophosgene equivalent is subjected to the reaction with ammonia or the amine of formula V.


Further details can be taken from the preparation examples contained herein. Apart from that, a skilled person will easily find suitable reaction conditions for the synthesis depicted in scheme 1 by routine.


In a similar manner a compound of formula (II′) can be reacted with an isothiocyanate compound (IV′), which has been prepared from primary amine (V), where R2b is H and R2a is different from H, to obtain a compound of the formula I, where R2b is H and R2a is different from H. The reaction is depicted in scheme 2:




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The compounds of the formulae (II) and (II′) are known, e.g. from WO 2017/102275 or can be easily prepared by analogy to the methods described in WO 2017/102275 or from the corresponding 3-nitrobenzamide compounds or 3-cyanobenzamide compounds by reduction of the 3-nitro group or 3-cyanao group, respectively, according to standard procedures.


The compounds of formula I, where R7 is in particular H, can also be prepared by the reaction depicted in scheme 3 below.




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Compounds of formula VI can be reacted with benzoyl compounds of formula VII to afford compounds of formula I, wherein R7 is hydrogen. Herein, X is a leaving group, such as halogen, in particular Cl, an anhydride residue or an active ester residue. Especially in case of X being halogen the reaction is suitably carried out in the presence of a base. Suitable bases are for example carbonates, such as lithium, sodium, potassium or cesium carbonates, amines, such as trimethylamine or triethylamine, and basic N-heterocycles, such as pyridine, 2,6-dimethylpyridine or 2,4,6-trimethylpyridine. Suitable solvents are in particular aprotic solvents such as pentane, hexane, heptane, octane, cyclohexane, dichloromethane, chloroform, 1,2-dichlorethane, benzene, chlorobenzene, toluene, the xylenes, dichlorobenzene, trimethylbenzene, pyridine, 2,6-dimethylpyridine, 2,4,6-trimethylpyridine, acetonitrile, diethyl ether, tetrahydrofuran, 2-methyl tetrahydrofuran, methyl tert-butylether, 1,4-dioxane, N,N-dimethyl formamide, N-methyl pyrrolidinone or mixtures thereof. The starting materials are generally reacted with one another in equimolar or nearly equimolar amounts at a reaction temperature usually in the range of −20° C. to 100° C. and preferably in the range of −5° C. to 50° C.


Alternatively, compounds of formula I can also be prepared as shown in scheme 4 below. Reaction of the amino compound of formula VI with a benzoic acid compound of formula VIII in the presence of an activating compound yields the compound of formula I, wherein R7 is in particular H. The reaction of compound (VI) with compound (VIII) is preferably carried out in the presence of a suitable activating agent which converts the carboxyl group of compound (VIII) into an activated ester or amide. For this purpose activating agents known in the art, such as 1,1′,carbonyldiimidazole (CDI), dicyclohexyl carbodiimide (DCC), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) or 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide (T3P) can be used. The activated ester or amide can be formed, depending in particular on the specific activating agent used, either in situ by contacting benzoic acid compound of formula VIII with the activating agent in the presence of the amine compound of the formula VI, or in a separate step prior to the reaction with amine compound of formula VIII. It may be advantageous, especially in cases where DCC or EDC are used as activating agent, to include further additives in the activating reaction, such as hydroxybenzotriazole (HOBt), nitro-phenol, pentafluorophenol, 2,4,5-trichlorophenol or N-hydroxysuccinimide. It may further be advantageous to prepare the activated ester or amide in the presence of a base, for example a tertiary amine. The activated ester or amide is either in situ or subsequently reacted with the amine of formula Ill or IV to afford the amide of formula I. The reaction normally takes place in anhydrous inert solvents, such as chlorinated hydrocarbons, e.g. dichloromethane or dichloro-ethane, ethers, e.g. tetrahydrofuran or 1,4-dioxane or carboxamides, e.g. N,N-dimethylformamide, N,N-dimethylacetamide or N-methylpyrrolidone. The reaction is frequently carried out at temperatures in the range from −20° C. to +50° C., depending on the reactivity of the compounds (VI) and (VIII), respectively, and the activating agent used.




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The compounds of formula VI are either commercially available or can be obtained according to standard methods of organic chemistry. For example, the compound of formula VI, where Q is Q1 and R6a is alkyl or a similar radical, can be prepared from 5-aminotetrazole according to the method described in the Journal of the American Chemical Society, 1954, 76, 923-924. Alternatively, compounds of formula VI, where Q is Q1, can be prepared according to the method described in the Journal of the American Chemical Society, 1954, 76, 88-89 starting from 3-(R6a)-substituted 1-aminoguandidines.


The compounds of formula VI, where Q is Q2 and R6b is alkyl or a similar radical, can be prepared from 3-amino-1,2,4-triazole according to the method described in Zeitschrift für Chemie, 1990, 30, 12, 436-437 by reacting 1-(R6b)-substituted 1-aminoguandidines and formic acid.


The compounds of formula VI, where Q is Q3 are either commercially available or can be prepared by analogy to standard methods for preparing 4-amino-1,2,5-oxadiazole compounds known from the literature. For example, 3-(R6c)-substituted-4-amino-1,2,5-oxadiazoles can be prepared from β-ketoesters pursuant to a procedure described in Russian Chemical Bulletin, Int. Ed., 54(4), 1032-1037 (2005). Compounds of formula VI, where Q is Q3 and where R6c is halogen, can be prepared from commercially available 3,4-diamino-1,2,5-oxadiazole according to procedures described in the literature, e.g. by the Sandmeyer-type reaction described in Heteroatom Chemistry, 15(3), 199-207 (2004). Compounds of formula VI, where Q is Q3 and where R6c is halogen, can be used as starting materials for introducing further substituents R6c by nucleophilic replacement in accordance to the methods described in Journal of Chemical Research, Synopses (6), 190 (1985), in Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (9), 2086-8 (1986) or in Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya), 53(3), 596-614 (2004).


The compounds of formula VI, where Q is Q4 are either known or can be prepared by analogy to standard methods for preparing 2-amino-1,3,4-oxadiazole compounds known from the literature. For example, 5-(R6d)-substituted-2-amino-1,3,4-oxadiazoles can be prepared from aldehydes and semicarbazide pursuant to a procedure described in J. Org. Chem., 2015, 80, 1018-1024. 5-(R6d)-substituted-2-amino-1,3,4-oxadiazoles can also be prepared by intramolecular cyclization of semicarbanzones by the protocol described in Synlett, 2015, 26, 1201-1206. Further methods for preparing 5-(R6d)-substituted-2-amino-1,2,5-oxadiazoles are described in Org. Lett., 2014, 16, 2342-2345, J. Org. Chem., 2006, Synlett, 2012, 23, 1970-1972 and J. Org. Chem., 2013, 78, 438-444.


The compounds of formulae VII and VIII can be prepared from the corresponding 3-aminobenzoic acid compounds according to standard procedures for preparing thio ureas, e.g. by analogy to the method depicted in schemes 1 and 2.


Apart from that, compounds of formula VI and the benzoic acid precursors of formulae VII and VIII are known or can also be prepared by processes known in the art.


Compounds of formula I, where R2b or R2c are different from hydrogen, can be prepared from compounds of formula I, where R2b or R2c are hydrogen by analogy to standard methods of N-substitution of ureas and thioureas respectively. Compounds of formula I, where R7 is different from hydrogen, can be prepared from compounds of formula I, where R7 is hydrogen by analogy to standard methods of N-substitution of carboxamides.


As a rule, the compounds of formula I including their stereoisomers, salts, and tautomers, and their precursors in the synthesis process, can be prepared by the methods described above. If individual compounds can not be prepared via the above-described routes, they can be prepared by derivatization of other compounds I or the respective precursor or by customary modifications of the synthesis routes described. For example, in individual cases, certain compounds of formula I can advantageously be prepared from other compounds of formula I by derivatization, e.g. by ester hydrolysis, amidation, esterification, ether cleavage, olefination, reduction, oxidation and the like, 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 on 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 trituration.


The compounds of formula I and their agriculturally suitable salts are useful as herbicides. They are useful as such or as an appropriately formulated composition. The herbicidal compositions comprising the compound of formula I, an N-oxide or a salt thereof, in particular the preferred aspects thereof, control vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leaved weeds and weed grasses in crops such as wheat, rice, corn, soybeans and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.


Depending on the application method in question, the compounds of formula I, in particular the preferred aspects thereof, or compositions comprising them can additionally be employed in a further number of crop plants for eliminating unwanted plants. Examples of suitable crops are the following:


Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Avena sativa, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Brassica oleracea, Brassica nigra, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pistacia vera, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Prunus armeniaca, Prunus cerasus, Prunus dulcis and Prunus domestica, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Sinapis alba, Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Vicia faba, Vitis vinifera, Zea mays.


The compounds of the present invention are particularly suitable for use in crops from the family poaceae, in particular crops of the tribum triticeae, e.g. crops of the generae hordeum, sorghum, triticium and secale, and crops of the generae zea, e.g. Zea mays and oryza, e.g. Oryza sativa.


The term “crop plants” also includes plants which have been modified by breeding, mutagenesis or genetic engineering. Genetically modified plants are plants whose genetic material has been modified in a manner which does not occur under natural conditions by crossing, mutations or natural recombination (i.e. reassembly of the genetic information). Here, in general, one or more genes are integrated into the genetic material of the plant to improve the properties of the plant.


Accordingly, the term “crop plants” also includes plants which, by breeding and genetic engineering, have acquired tolerance to certain classes of herbicides, such as hydroxy-phenylpyruvate dioxygenase (HPPD) inhibitors, acetolactate synthase (ALS) inhibitors, such as, for example, sulfonylureas (EP-A-0257993, U.S. Pat. No. 5,013,659) or imidazolinones (see, for example, 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, for example, glyphosate (see, for example, WO 92/00377), glutamine synthetase (GS) inhibitors, such as, for example, glufosinate (see, for example, EP-A-0242236, EP-A-242246), or oxynil herbicides (see, for example, U.S. Pat. No. 5,559,024).


In a preferred embodiment, the term “crop plants” refers to plants that comprise in their genomes a gene encoding a herbicide-tolerant wild-type or mutated HPPD protein. Such a gene may be an endogenous gene or a transgene, as described hereinafter.


By a “herbicide-tolerant” or “herbicide-resistant” plant, it is intended that a plant that is tolerant or resistant to at least one herbicide at a level that would normally kill, or inhibit the growth of, a normal or wild-type plant. By “herbicide-tolerant wild-type or mutated HPPD protein” or “herbicide-resistant wild-type or mutated HPPD protein”, it is intended that such a HPPD protein displays higher HPPD activity, relative to the HPPD activity of a wild-type or reference HPPD protein, when in the presence of at least one herbicide that is known to interfere with HPPD activity and at a concentration or level of the herbicide that is known to inhibit the HPPD activity of the reference wild-type HPPD protein. Furthermore, the HPPD activity of such a herbicide-tolerant or herbicide-resistant HPPD protein may be referred to herein as “herbicide-tolerant” or “herbicide-resistant” HPPD activity.


The term “mutated HPPD nucleic acid” refers to an HPPD nucleic acid having a sequence that is mutated from a wild-type HPPD nucleic acid and that confers increased “HPPD-inhibiting herbicide” tolerance to a plant in which it is expressed. Furthermore, the term “mutated hydroxyphenyl pyruvate dioxygenase (mutated HPPD)” refers to the replacement of an amino acid of the wild-type primary sequences SEQ ID NO: 2, 5, 8, 11, 14, 17, 20, 22, 24, 26, 28, 30, 32, 34, 36, 38, 40, 42, 44, 46, 48, 50, 53, 55, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, a variant, a derivative, a homologue, an orthologue, or paralogue thereof, with another amino acid. The expression “mutated amino acid” will be used below to designate the amino acid which is replaced by another amino acid, thereby designating the site of the mutation in the primary sequence of the protein.


Several HPPDs and their primary sequences have been described in the state of the art, in particular the HPPDs of bacteria such as Pseudomonas (Ruetschi et al., Eur.J.Biochem., 205, 459-466, 1992, WO96/38567), of plants such as Arabidopsis (WO96/38567, Genebank AF047834) or of carrot (WO96/38567, Genebank 87257), of Coccicoides (Genebank COITRP), HPPDs of Brassica, cotton, Synechocystis, and tomato (U.S. Pat. No. 7,297,541), of mammals such as the mouse or the pig. Furthermore, artificial HPPD sequences have been described, for example in U.S. Pat. Nos. 6,768,044; 6,268,549;


In a preferred embodiment, the nucleotide sequence of (i) comprises the sequence of SEQ ID NO: 1, 51, 3, 4, 6, 7, 9, 10, 12, 13, 15, 16, 18, 19, 21, 23, 25, 27, 29, 31, 33, 35, 37, 39, 41, 43, 45, 47, 49, 52, 54, 56, 68, 69 or a variant or derivative thereof.


In a particularly preferred embodiment, the mutated HPPD nucleic acid useful for the present invention comprises a mutated nucleic acid sequence of SEQ ID NO: 1 or SEQ ID NO: 52, or a variant or derivative thereof.


Furthermore, it will be understood by the person skilled in the art that the nucleotide sequences of (i) or (ii) encompass homologues, paralogues and orthologues of SEQ ID NO: 1, 51, 3, 4, 6, 7, 9, 10, 12, 13, 15, 16, 18, 19, 21, 23, 25, 27, 29, 31, 33, 35, 37, 39, 41, 43, 45, 47, 49, 52, 54, 56, 68, 69, as defined hereinafter.


The term “variant” with respect to a sequence (e.g., a polypeptide or nucleic acid sequence such as—for example—a transcription regulating nucleotide sequence of the invention) is intended to mean substantially similar sequences. For nucleotide sequences comprising an open reading frame, variants include those sequences that, because of the degeneracy of the genetic code, encode the identical amino acid sequence of the native protein. Naturally occurring allelic variants such as these can be identified with the use of well-known molecular biology techniques, as, for example, with polymerase chain reaction (PCR) and hybridization techniques. Variant nucleotide sequences also include synthetically derived nucleotide sequences, such as those generated, for example, by using site-directed mutagenesis and for open reading frames, encode the native protein, as well as those that encode a polypeptide having amino acid substitutions relative to the native protein. Generally, nucleotide sequence variants of the invention will have at least 30, 40, 50, 60, to 70%, e.g., preferably 71%, 72%, 73%, 74%, 75%, 76%, 77%, 78%, to 79%, generally at least 80%, e.g., 81%-84%, at least 85%, e.g., 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97%, to 98% and 99% nucleotide “sequence identity” to the nucleotide sequence of SEQ ID NO:1, 51, 3, 4, 6, 7, 9, 10, 12, 13, 15, 16, 18, 19, 21, 23, 25, 27, 29, 31, 33, 35, 37, 39, 41, 43, 45, 47, 49, 52, 54, 56, 68, 69, 47, or 49. By “variant” polypeptide is intended a polypeptide derived from the protein of SEQ ID NO: 2, 5, 8, 11, 14, 17, 20, 22, 24, 26, 28, 30, 32, 34, 36, 38, 40, 42, 44, 46, 48, 50, 53, 55, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, by deletion (so-called truncation) or addition of one or more amino acids to the N-terminal and/or C-terminal end of the native protein; deletion or addition of one or more amino acids at one or more sites in the native protein; or substitution of one or more amino acids at one or more sites in the native protein. Such variants may result from, for example, genetic polymorphism or from human manipulation. Methods for such manipulations are generally known in the art.


In a preferred embodiment, variants of the polynucleotides useful for the present invention will have at least 30, 40, 50, 60, to 70%, e.g., preferably 71%, 72%, 73%, 74%, 75%, 76%, 77%, 78%, to 79%, generally at least 80%, e.g., 81%-84%, at least 85%, e.g., 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97%, to 98% and 99% nucleotide “sequence identity” to the nucleotide sequence of SEQ ID NO:1, 47, 49, or SEQ ID NO: 52.


It is recognized that the polynucleotide molecules and polypeptides of the invention encompass polynucleotide molecules and polypeptides comprising a nucleotide or an amino acid sequence that is sufficiently identical to nucleotide sequences set forth in SEQ ID NOs: 1, 51, 3, 4, 6, 7, 9, 10, 12, 13, 15, 16, 18, 19, 21, 23, 25, 27, 29, 31, 33, 35, 37, 39, 41, 43, 45, 47, 49, 52, 54, 56, 68, 69, 47, or 49, or to the amino acid sequences set forth in SEQ ID NOs: 2, 5, 8, 11, 14, 17, 20, 22, 24, 26, 28, 30, 32, 34, 36, 38, 40, 42, 44, 46, 48, 50, 53, 55, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 48, or 50. The term “sufficiently identical” is used herein to refer to a first amino acid or nucleotide sequence that contains a sufficient or minimum number of identical or equivalent (e.g., with a similar side chain) amino acid residues or nucleotides to a second amino acid or nucleotide sequence such that the first and second amino acid or nucleotide sequences have a common structural domain and/or common functional activity.


“Sequence identity” refers to the extent to which two optimally aligned DNA or amino acid sequences are invariant throughout a window of alignment of components, e.g., nucleotides or amino acids. An “identity fraction” for aligned segments of a test sequence and a reference sequence is the number of identical components that are shared by the two aligned sequences divided by the total number of components in reference sequence segment, i.e., the entire reference sequence or a smaller defined part of the reference sequence. “Percent identity” is the identity fraction times 100. Optimal alignment of sequences for aligning a comparison window are well known to those skilled in the art and may be conducted by tools such as the local homology algorithm of Smith and Waterman, the homology alignment algorithm of Needleman and Wunsch, the search for similarity method of Pearson and Lipman, and preferably by computerized implementations of these algorithms such as GAP, BESTFIT, FASTA, and TFASTA available as part of the GCG. Wisconsin Package. (Accelrys Inc. Burlington, Mass.)


The terms “polynucleotide(s)”, “nucleic acid sequence(s)”, “nucleotide sequence(s)”, “nucleic acid(s)”, “nucleic acid molecule” are used interchangeably herein and refer to nucleotides, either ribonucleotides or deoxyribonucleotides or a combination of both, in a polymeric unbranched form of any length.


“Derivatives” of a protein encompass peptides, oligopeptides, polypeptides, proteins and enzymes having amino acid substitutions, deletions and/or insertions relative to the unmodified protein in question and having similar biological and functional activity as the unmodified protein from which they are derived.


“Homologues” of a protein encompass peptides, oligopeptides, polypeptides, proteins and enzymes having amino acid substitutions, deletions and/or insertions relative to the unmodified protein in question and having similar biological and functional activity as the unmodified protein from which they are derived.


A deletion refers to removal of one or more amino acids from a protein.


An insertion refers to one or more amino acid residues being introduced into a predetermined site in a protein. Insertions may comprise N-terminal and/or C-terminal fusions as well as intra-sequence insertions of single or multiple amino acids. Generally, insertions within the amino acid sequence will be smaller than N- or C-terminal fusions, of the order of about 1 to 10 residues. Examples of N- or C-terminal fusion proteins or peptides include the binding domain or activation domain of a transcriptional activator as used in the yeast two-hybrid system, phage coat proteins, (histidine)-6-tag, glutathione S-transferase-tag, protein A, maltose-binding protein, dihydrofolate reductase, Tag•100 epitope, c-myc epitope, FLAG®-epitope, IacZ, CMP (calmodulin-binding peptide), HA epitope, protein C epitope and VSV epitope.


A substitution refers to replacement of amino acids of the protein with other amino acids having similar properties (such as similar hydrophobicity, hydrophilicity, antigenicity, propensity to form or break α-helical structures or β-sheet structures). Amino acid substitutions are typically of single residues, but may be clustered depending upon functional constraints placed upon the polypeptide and may range from 1 to 10 amino acids; insertions will usually be of the order of about 1 to 10 amino acid residues. The amino acid substitutions are preferably conservative amino acid substitutions. Conservative substitution tables are well known in the art (see for example Creighton (1984) Proteins. W.H. Freeman and Company (Eds).


Amino acid substitutions, deletions and/or insertions may readily be made using peptide synthetic techniques well known in the art, such as solid phase peptide synthesis and the like, or by recombinant DNA manipulation. Methods for the manipulation of DNA sequences to produce substitution, insertion or deletion variants of a protein are well known in the art. For example, techniques for making substitution mutations at predetermined sites in DNA are well known to those skilled in the art and include M13 mutagenesis, T7-Gen in vitro mutagenesis (USB, Cleveland, Ohio), QuikChange Site Directed mutagenesis (Stratagene, San Diego, Calif.), PCR-mediated site-directed mutagenesis or other site-directed mutagenesis protocols.


“Derivatives” further include peptides, oligopeptides, polypeptides which may, compared to the amino acid sequence of the naturally-occurring form of the protein, such as the protein of interest, comprise substitutions of amino acids with non-naturally occurring amino acid residues, or additions of non-naturally occurring amino acid residues. “Derivatives” of a protein also encompass peptides, oligopeptides, polypeptides which comprise naturally occurring altered (glycosylated, acylated, prenylated, phosphorylated, myristoylated, sulphated etc.) or non-naturally altered amino acid residues compared to the amino acid sequence of a naturally-occurring form of the polypeptide. A derivative may also comprise one or more non-amino acid substituents or additions compared to the amino acid sequence from which it is derived, for example a reporter molecule or other ligand, covalently or non-covalently bound to the amino acid sequence, such as a reporter molecule which is bound to facilitate its detection, and non-naturally occurring amino acid residues relative to the amino acid sequence of a naturally-occurring protein. Furthermore, “derivatives” also include fusions of the naturally-occurring form of the protein with tagging peptides such as FLAG, HIS6 or thioredoxin (for a review of tagging peptides, see Terpe, Appl. Microbiol. Biotechnol. 60, 523-533, 2003).


“Orthologues” and “paralogues” encompass evolutionary concepts used to describe the ancestral relationships of genes. Paralogues are genes within the same species that have originated through duplication of an ancestral gene; orthologues are genes from different organisms that have originated through speciation, and are also derived from a common ancestral gene.


It is well-known in the art that paralogues and orthologues may share distinct domains harboring suitable amino acid residues at given sites, such as binding pockets for particular substrates or binding motifs for interaction with other proteins.


The term “domain” refers to a set of amino acids conserved at specific positions along an alignment of sequences of evolutionarily related proteins. While amino acids at other positions can vary between homologues, amino acids that are highly conserved at specific positions indicate amino acids that are likely essential in the structure, stability or function of a protein. Identified by their high degree of conservation in aligned sequences of a family of protein homologues, they can be used as identifiers to determine if any polypeptide in question belongs to a previously identified polypeptide family.


The term “motif” or “consensus sequence” refers to a short conserved region in the sequence of evolutionarily related proteins. Motifs are frequently highly conserved parts of domains, but may also include only part of the domain, or be located outside of conserved domain (if all of the amino acids of the motif fall outside of a defined domain).


Specialist databases exist for the identification of domains, for example, SMART (Schultz et al. (1998) Proc. Natl. Acad. Sci. USA 95, 5857-5864; Letunic et al. (2002) Nucleic Acids Res 30, 242-244), InterPro (Mulder et al., (2003) Nucl. Acids. Res. 31, 315-318), Prosite (Bucher and Bairoch (1994), A generalized profile syntax for biomolecular sequences motifs and its function in automatic sequence interpretation. (In) ISMB-94; Proceedings 2nd International Conference on Intelligent Systems for Molecular Biology. Altman R., Brutlag D., Karp P., Lathrop R., Searls D., Eds., pp 53-61, AAAI Press, Menlo Park; Hulo et al., Nucl. Acids. Res. 32:0134-D137, (2004)), or Pfam (Bateman et al., Nucleic Acids Research 30(1): 276-280 (2002)). A set of tools for in silico analysis of protein sequences is available on the ExPASy proteomics server (Swiss Institute of Bioinformatics (Gasteiger et al., ExPASy: the proteomics server for in-depth protein knowledge and analysis, Nucleic Acids Res. 31:3784-3788(2003)). Domains or motifs may also be identified using routine techniques, such as by sequence alignment.


Methods for the alignment of sequences for comparison are well known in the art, such methods include GAP, BESTFIT, BLAST, FASTA and TFASTA. GAP uses the algorithm of Needleman and Wunsch ((1970) J Mol Biol 48: 443-453) to find the global (i.e. spanning the complete sequences) alignment of two sequences that maximizes the number of matches and minimizes the number of gaps. The BLAST algorithm (Altschul et al. (1990) J Mol Biol 215: 403-10) calculates percent sequence identity and performs a statistical analysis of the similarity between the two sequences. The software for performing BLAST analysis is publicly available through the National Centre for Biotechnology Information (NCBI). Homologues may readily be identified using, for example, the ClustalW multiple sequence alignment algorithm (version 1.83), with the default pairwise alignment parameters, and a scoring method in percentage. Global percentages of similarity and identity may also be determined using one of the methods available in the MatGAT software package (Campanella et al., BMC Bioinformatics. 2003 Jul. 10; 4:29. MatGAT: an application that generates similarity/identity matrices using protein or DNA sequences). Minor manual editing may be performed to optimise alignment between conserved motifs, as would be apparent to a person skilled in the art. Furthermore, instead of using full-length sequences for the identification of homologues, specific domains may also be used. The sequence identity values may be determined over the entire nucleic acid or amino acid sequence or over selected domains or conserved motif(s), using the programs mentioned above using the default parameters. For local alignments, the Smith-Waterman algorithm is particularly useful (Smith T F, Waterman M S (1981) J. Mol. Biol 147(1); 195-7).


By substituting one or more of the key amino acid residues, the herbicide tolerance or resistance of a plant to the herbicide as described herein could be remarkably increased as compared to the activity of the wild type HPPD enzymes with SEQ ID NO: 2, 5, 8, 11, 14, 17, 20, 22, 24, 26, 28, 30, 32, 34, 36, 38, 40, 42, 44, 46, 48, 50, 53, 55, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67. Preferred substitutions of mutated HPPD are those that increase the herbicide tolerance of the plant, but leave the biological activity of the dioxygenase activity substantially unaffected.


It will be understood by the person skilled in the art that amino acids located in a close proximity to the positions of amino acids mentioned below may also be substituted. Thus, in another embodiment the mutated HPPD useful for the present invention comprises a sequence of SEQ ID NO: 2, 5, 8, 11, 14, 17, 20, 22, 24, 26, 28, 30, 32, 34, 36, 38, 40, 42, 44, 46, 48, 50, 53, 55, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, or a variant, derivative, orthologue, paralogue or homologue thereof, wherein an amino acid ±3, ±2 or ±1 amino acid positions from a key amino acid is substituted by any other amino acid.


Based on techniques well-known in the art, a highly characteristic sequence pattern can be developed, by means of which further of mutated HPPD candidates with the desired activity may be searched.


Searching for further mutated HPPD candidates by applying a suitable sequence pattern would also be encompassed by the present invention. It will be understood by a skilled reader that the present sequence pattern is not limited by the exact distances between two adjacent amino acid residues of said pattern. Each of the distances between two neighbours in the above patterns may, for example, vary independently of each other by up to ±10, ±5, ±3, ±2 or ±1 amino acid positions without substantially affecting the desired activity.


In line with said above functional and spatial analysis of individual amino acid residues based on the crystallographic data as obtained according to the present invention, unique partial amino acid sequences characteristic of potentially useful mutated HPPD candidates of the invention may be identified.


In a particularly preferred embodiment, the mutated HPPD refers to a variant or derivative of SEQ ID NO: 2 wherein the substitutions are selected from the following Table 49a.









TABLE 49a







(Sequence ID No: 2): single amino acid substitutions










Key amino acid position
Substituents







Val212
Ile, Leu



Val213
Thr, Ala



Asn215
Ala, His



Ala236
Leu, Ser, Arg



Phe238
Val, Ala



Leu250
Val, Met



Ser252
Thr



Pro265
Ala



Asn267
Tyr, Gln



Gln278
His, Asn, Ser



Ile279
Thr



Arg309
Lys, Ala



Leu320
Asn, Gln, His, Tyr,



Pro321
Ala, Arg, Gly, Asn



Leu334
Glu, Cys



Leu353
Met, Tyr, Ala, Ser



Phe366
Ile, Leu, Tyr



Gly371
Ile, Phe



Thr375
Pro



Phe377
Ala, Leu, Ser



Gly403
Arg



Phe404
Leu, Pro



Lys406
Thr



Gly407
Cys, His



Phe409
Ile, His



Glu411
Thr



Leu412
Met, Phe, Trp, Ala, Ser



Ile416
Val, Phe



Ser410
Gly



Val254
Ala










Furthermore, by substituting at least two of the key amino acid residues of SEQ ID NO: 2 with specific residues, the herbicide tolerance or resistance could be remarkably increased as compared to the activity of the wild type HPPD enzymes or HPPD enzymes in which only one amino acid residue had been substituted. Therefore, in another preferred embodiment, the variant or derivative of the mutated HPPD refers to a polypeptide of SEQ ID NO: 2, wherein two, three, four or five key amino acids are substituted by another amino acid residue. Particularly preferred double, triple, quadruple, or quintuple mutations are described in Table 49b.









TABLE 49b







(with reference to Sequence ID No: 2): combined amino acid


substitutions








Combination



No
Key amino acid position and and its substitutents











1
A236L, E411T


2
L320H, P321A


3
L320H, P321R


4
L320N, P321A


5
L320N, P321R


6
L320Q, P321A


7
L320Q, P321R


8
L320Y, P321A


9
L320Y, P321R


10
L353M, P321R


11
L353M, P321R, A236L


12
L353M, P321R, A236L, E411T


13
L353M, P321R, E411T


14
L353M, P321R, L320H


15
L353M, P321R, L320N


16
L353M, P321R, L320Q


17
L353M, P321R, L320Y


18
L353M, P321R, V212I


19
L353M, P321R, V212I, L334E


20
L353M, P321R, V212L, L334E


21
L353M, P321R, V212L, L334E, A236L


22
L353M, P321R, V212L, L334E, A236L, E411T


23
L353M, P321R, V212L, L334E, E411T


24
L353M, P321R, V212L, L334E, L320H


25
L353M, P321R, V212L, L334E, L320N


26
L353M, P321R, V212L, L334E, L320Q


27
L353M, P321R, V212L, L334E, L320Y


28
L353M, V212I









In a particularly preferred embodiment, the mutated HPPD enzyme comprising a polypeptide of SEQ ID NO: 2, a variant, derivative, homologue, paralogue or orthologue thereof, useful for the present invention comprises one or more of the following: the amino acid corresponding to or at position 320 is histidine, asparagine or glutamine; the amino acid position 334 is glutamic acid; the amino acid position 353 is methionine; the amino acid corresponding to or at position 321 alanine or arginine; the amino acid corresponding to or at position 212 is isoleucine.


In an especially particularly preferred embodiment, the mutated HPPD refers to a polypeptide comprising SEQ ID NO: 2, wherein the leucine corresponding to or at position 320 is substituted by a histidine, and the proline corresponding to or at position 321 is substituted by an alanine.


In another especially particularly preferred embodiment, the mutated HPPD refers to a polypeptid comprising SEQ ID NO:2, wherein Leucine corresponding to or at position 353 is substituted by a Methionine, the Proline corresponding to or at position 321 is substituted by an Arginine, and the Leucine corresponding to or at position 320 is substituted by an Asparagine.


In another especially particularly preferred embodiment, the mutated HPPD refers to a polypeptide comprising SEQ ID NO: 2, wherein the Leucine corresponding to or at position 353 is substituted by a Methionine, the Proline corresponding to or at position 321 is substituted by an Arginine, and the Leucine corresponding to or at position 320 is substituted by a glutamine.


In another preferred embodiment, the mutated HPPD refers to a variant or derivative of SEQ ID NO: 53 wherein the substitutions are selected from the following Table 49c.









TABLE 49c







(Sequence ID No: 53): single amino acid substitutions









Key




amino acid

Preferred


position
Substituents
substituents





Val228
Thr, Ala
Thr, Ala


Asn230
Ala, His
Ala, His


Ala251
Ser, Arg
Ser, Arg


Phe253
Val, Ala
Val, Ala


Leu265
Val, Met
Val, Met


Ser267
Thr
Thr


Pro280
Ala
Ala


Asn282
Tyr, Gln
Tyr, Gln


Lys291
Arg, Ala
Arg


Gln293
Ala, Leu, Ile, Val, His, Asn, Ser
His, Asn, Ser


Ile294
Thr
Thr


Arg324
Lys, Ala
Lys, Ala


Met335
Ala, Trp, Phe, Leu, Ile, Val, Asn, Gln,
Gln, Asn, His, Tyr



His, Tyr, Ser, Thr, Cys



Pro336
Ala, Arg, Gly, Asn
Ala, Gly


Ser337
Ala, Pro, Thr
Pro, Thr


Pro339
Deletion
Deletion


Pro340
Gly
Gly


Glu363
Gln
Gln


Leu368
Met, Tyr,
Met


Phe381
Ile, Leu, Tyr
Ile, Leu


Leu385
Ala, Val, Gln, Asp
Val, Asp


Gly386
Ile, Phe
Ile, Phe


Thr390
Pro
Pro


Phe392
Ala, Leu, Ser
Ala


Ile393
Ala, Leu, Phe, Val
Leu


Phe419
Leu, Pro
Leu, Pro


Lys421
Thr
Thr


Gly422
His, Met, Phe, Cys
His, Cys


Phe424
Ile, His
Ile, His


Leu427
Phe, Trp, Ala, Ser, Met
Phe


Ile431
Val, Phe
Val, Phe


Ser425
Gly
Gly


Val269
Ala
Ala









In another preferred embodiment, the variant or derivative of the mutated HPPD useful for the present invention refers to a polypeptide of SEQ ID NO: 53, a homologue, orthologue, or paralogue thereof, wherein two, three, four or five key amino acids are substituted by another amino acid residue. Particularly preferred double, triple, quadruple, or quintuple mutations are described in Table 49d.









TABLE 49d







(reference to Sequence ID No: 53): combined amino acid substitutions










Combination
Key amino

Preferred


No
acid position
Substituents
substituents





1
Pro336
Ala, Arg
Ala



Glu363
Gln
Gln


2
Pro336
Ala, Arg
Ala



Glu363
Gln
Gln



Leu385
Ala, Val
Val


3
Pro336
Ala, Arg
Ala



Glu363
Gln
Gln



Leu385
Ala, Val
Val



Ile393
Ala, Leu
Leu


4
Leu385
Ala, Val
Val



Ile393
Ala, Leu
Leu


5
Met335
Ala, Trp, Phe, Leu, Ile,
Gln, Asn,




Val, Asn, Gln, His, Tyr,
His, Tyr




Ser, Thr, Cys




Pro336
Ala, Arg, Gly
Ala, Gly


6
Met335
Ala, Trp, Phe, Leu, Ile,
Gln, Asn,




Val, Asn, Gln, His, Tyr,
His, Tyr




Ser, Thr, Cys




Pro336
Ala, Arg, Gly
Ala, Gly



Glu363
Gln
Gln


7
Met335
Ala, Trp, Phe, Leu, Ile,
Gln, Asn, His,




Val, Asn, Gln, His, Tyr,
Tyr, Leu




Ser, Thr, Cys




Pro336
Ala, Arg, Gly
Ala, Arg, Gly



Ser337
Ala, Pro, Thr
Pro, Thr



Pro339
Deletion
Deletion



Pro340
Gly
Gly









Furthermore, by substituting the amino acids at some positions in the HPPD polypeptide sequences of Scenedesmus obliquus, the tolerance of crop plants as described herein towards the herbicides as described herein could be remarkably increased.


Thus, in a preferred embodiment, the mutated HPPD of the present invention comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, which comprises one or more of the following:


the amino acid corresponding to or at position 30 is other than proline, the amino acid corresponding to or at position 39 is other than Phe, the amino acid corresponding to or at position 54 is other than Gly, the amino acid corresponding to or at position 57 is other than Met, the amino acid corresponding to or at position 84 is other than Phe, the amino acid corresponding to or at position 210 is other than Val, the amino acid corresponding to or at position 212 is other than Asn, the amino acid corresponding to or at position 223 is other than Val, the amino acid corresponding to or at position 243 is other than Val, the amino acid corresponding to or at position 247 is other than Leu, the amino acid corresponding to or at position 249 is other than Ser, the amino acid corresponding to or at position 251 is other than Val, the amino acid corresponding to or at position 264 is other than Asn, the amino acid corresponding to or at position 291 is other than Leu, the amino acid corresponding to or at position 306 is other than His, the amino acid corresponding to or at position 317 is other than Gin, the amino acid corresponding to or at position 318 is other than Ala, the amino acid corresponding to or at position 319 is other than Ala, the amino acid corresponding to or at position 321 is other than Gly, the amino acid corresponding to or at position 326 is other than Lys, the amino acid corresponding to or at position 327 is other than Arg, the amino acid corresponding to or at position 331 is other than Lys, the amino acid corresponding to or at position 341 is other than Trp, the amino acid corresponding to or at position 342 is other than Ala, the amino acid corresponding to or at position 345 is other than Glu, the amino acid corresponding to or at position 350 is other than Leu, the amino acid corresponding to or at position 363 is other than Phe, the amino acid corresponding to or at position 367 is other than Leu, the amino acid corresponding to or at position 373 is other than Ile, the amino acid corresponding to or at position 374 is other than Phe, the amino acid corresponding to or at position 375 is other than Ile, the amino acid corresponding to or at position 379 is other than Glu, the amino acid corresponding to or at position 405 is other than Gly, the amino acid corresponding to or at position 407 is other than Phe, the amino acid corresponding to or at position 410 is other than Gly, the amino acid corresponding to or at position 412 is other than Phe, the amino acid corresponding to or at position 414 is other than Glu, the amino acid corresponding to or at position 419 is other than lie, the amino acid corresponding to or at position 421 is other than Glu, the amino acid corresponding to or at position 422 is other than Tyr.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 367 is Val, and the amino acid corresponding to or at position 375 is Leu.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 367 is Val, and the amino acid corresponding to or at position 375 is Leu, and the amino acid corresponding to or at position 39 is Leu.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 367 is Val, and the amino acid corresponding to or at position 375 is Leu, and the amino acid corresponding to or at position 39 is Trp.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 345 is Ala, Arg, Asn, Asp, Cys, Gln, Gly, His, Ile, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val, particularly preferred Gln


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 345 is Gln, and the amino acid corresponding to or at position 341 is Ile.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 345 is Gln, and the amino acid corresponding to or at position 326 is Glu.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 345 is Gln, and the amino acid corresponding to or at position 326 is Asp.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 345 is Gln, and the amino acid corresponding to or at position 326 is Gln.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 318 is Arg, Asn, Asp, Cys, Gln, Glu, Gly, His, Ile, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val, particularly preferred Pro.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 319 is Arg, Asn, Asp, Cys, Gln, Glu, Gly, His, Ile, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, Val, particularly preferred Pro.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 318 is Pro, and the amino acid corresponding to or at position 319 is Pro.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 321 is Ala, Arg, Asn, Asp, Cys, Gln, Glu, His, Ile, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 350 is Ala, Arg, Asn, Asp, Cys, Gln, Glu, Gly, His, lie, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val, particularly preferred Met.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 405 is Ala, Arg, Asn, Asp, Cys, Gln, Glu, His, Ile, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 251 is Ala, Arg, Asn, Asp, Cys, Gln, Glu, Gly, His, Ile, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, or Tyr, particularly preferred Ala.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 317 is Ala, Arg, Asn, Asp, Cys, Glu, Gly, His, Ile, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val, particularly preferred His or Met.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 379 is Ala, Arg, Asn, Asp, Cys, Gln, Gly, His, Ile, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val, particularly preferred Gln.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 350 is Met, and the amino acid corresponding to or at position 318 is Arg.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 350 is Met, and the amino acid corresponding to or at position 318 is Gly.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 350 is Met, and the amino acid corresponding to or at position 318 is Arg, and the amino acid corresponding to or at position 317 is Asn.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 210 is Ala, Arg, Asn, Asp, Cys, Gln, Glu, Gly, His, Ile, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, or Tyr.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 317 is His, and the amino acid corresponding to or at position 318 is Gly, and the amino acid corresponding to or at position 345 is Gln.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 317 is Met, and the amino acid corresponding to or at position 318 is Gly, and the amino acid corresponding to or at position 345 is Gln.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 363 is Ala, Arg, Asn, Asp, Cys, Gln, Glu, Gly, His, Ile, Leu, Lys, Met, Pro, Ser, Thr, Trp, Tyr, or Val, particularly preferred Ile.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 419 is Ala, Arg, Asn, Asp, Cys, Gln, Glu, Gly, His, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val, particularly preferred Val.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 249 is Ala, Arg, Asn, Asp, Cys, Gln, Glu, Gly, His, Ile, Leu, Lys, Met, Phe, Pro, Thr, Trp, Tyr, or Val.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 247 is Ala, Arg, Asn, Asp, Cys, Gln, Glu, Gly, His, Ile, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 407 is Ala, Arg, Asn, Asp, Cys, Gln, Glu, Gly, His, Ile, Leu, Lys, Met, Pro, Ser, Thr, Trp, Tyr, or Val.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 306 is Ala, Arg, Asn, Asp, Cys, Gln, Glu, Gly, Ile, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val, particularly preferred Lys.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 30 is Ala, Arg, Asn, Asp, Cys, Gln, Glu, Gly, His, Ile, Leu, Lys, Met, Phe, Ser, Thr, Trp, Tyr, or Val.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 54 is Ala, Arg, Asn, Asp, Cys, Gln, Glu, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 57 is Ala, Arg, Asn, Asp, Cys, Gln, Glu, Gly, His, Ile, Leu, Lys, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 84 is Ala, Arg, Asn, Asp, Cys, Gln, Glu, Gly, His, Ile, Leu, Lys, Met, Pro, Ser, Thr, Trp, Tyr, or Val.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 212 is Ala, Arg, Asp, Cys, Gln, Glu, Gly, His, Ile, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 223 is Ala, Arg, Asn, Asp, Cys, Gln, Glu, Gly, His, Ile, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, or Tyr.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 243 is Ala, Arg, Asn, Asp, Cys, Gln, Glu, Gly, His, Ile, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, or Tyr.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 264 is Ala, Arg, Asp, Cys, Gln, Glu, Gly, His, Ile, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 291 is Ala, Arg, Asn, Asp, Cys, Gln, Glu, Gly, His, Ile, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 327 is Ala, Asn, Asp, Cys, Gln, Glu, Gly, His, Ile, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 331 is Ala, Arg, Asn, Asp, Cys, Gln, Glu, Gly, His, Ile, Leu, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 342 is Arg, Asn, Asp, Cys, Gln, Glu, Gly, His, Ile, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 373 is Ala, Arg, Asn, Asp, Cys, Gln, Glu, Gly, His, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 374 is Ala, Arg, Asn, Asp, Cys, Gln, Glu, Gly, His, Ile, Leu, Lys, Met, Pro, Ser, Thr, Trp, Tyr, or Val.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 410 is Ala, Arg, Asn, Asp, Cys, Gln, Glu, His, Ile, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 412 is Ala, Arg, Asn, Asp, Cys, Gln, Glu, Gly, His, Ile, Leu, Lys, Met, Pro, Ser, Thr, Trp, Tyr, or Val.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 414 is Ala, Arg, Asn, Asp, Cys, Gln, Gly, His, Ile, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 421 is Ala, Arg, Asn, Asp, Cys, Gln, Gly, His, Ile, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 422 is Ala, Arg, Asn, Asp, Cys, Gln, Glu, Gly, His, Ile, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, or Val.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 251 is Ala, and the amino acid corresponding to or at position 405 is Asp.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 327 is Gly, and the amino acid corresponding to or at position 421 is Asp.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 251 is Ala, and the amino acid corresponding to or at position 306 is Arg, and the amino acid corresponding to or at position 317 is Leu, and the amino acid corresponding to or at position 318 is Pro, and the amino acid corresponding to or at position 321 is Pro, and the amino acid corresponding to or at position 331 is Glu, and the amino acid corresponding to or at position 350 is Met.


In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:


the amino acid corresponding to or at position 407 is Ala, Arg, Asn, Asp, Cys, Gln, Glu, Gly, His, Ile, Leu, Lys, Met, Pro, Ser, Thr, Trp, Tyr, or Val.


Following mutagenesis of one of the sequences as shown herein, the encoded protein can be expressed recombinantly and the activity of the protein can be determined using, for example, assays described herein.


It will be within the knowledge of the skilled artisan to identify conserved regions and motifs shared between the homologues, orthologues and paralogues of SEQ ID NO: 2, 5, 8, 11, 14, 17, 20, 22, 24, 26, 28, 30, 32, 34, 36, 38, 40, 42, 44, 46, 48, 50, 53, 55, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, and respectively SEQ ID NO: 48 or 50. Having identified such conserved regions that may represent suitable binding motifs, amino acids corresponding to the amino acids listed in Table 49a and 49b, 49c, and 49d can be chosen to be substituted by any other amino acid by conserved amino acids, and more preferably by the amino acids of tables 49a and 49b, 49c, and 49d.


Numerous crop plants, for example Clearfield® oilseed rape, tolerant to imidazolinones, for example imazamox, have been generated with the aid of classic breeding methods (muta-genesis). Crop plants such as soybeans, cotton, corn, beet and oilseed rape, resistant to glyphosate or glufosinate, which are available under the tradenames RoundupReady® (glyphosate) and Liberty Link® (glufosinate) have been generated with the aid of genetic engineering methods.


Accordingly, the term “crop plants” also includes plants which, with the aid of genetic engineering, produce one or more toxins, for example those of the bacterial strain Bacillus ssp. Toxins which are produced by such genetically modified plants include, for example, insecticidal proteins of Bacillus spp., in particular B. thuringiensis, such as the endotoxins Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9c, Cry34Ab1 or Cry35Ab1; or vegetative insecticidal proteins (VIPs), for example VIP1, VIP2, VIP3, or VIP3A; insecticidal proteins of nematode-colonizing bacteria, for example Photorhabdus spp. or Xenorhabdus spp.; toxins of animal organisms, for example wasp, spider or scorpion toxins; fungal toxins, for example from Streptomycetes; plant lectins, for example from peas or barley; agglutinins; proteinase inhibitors, for example trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors, ribo-some-inactivating proteins (RIPs), for example ricin, corn-RIP, abrin, luffin, saporin or bryodin; steroid-metabolizing enzymes, for example 3-hydroxysteroid oxidase, ecdysteroid-IDP glycosyl transferase, cholesterol oxidase, ecdysone inhibitors, or HMG-CoA reductase; ion channel blockers, for example inhibitors of sodium channels or calcium channels; juvenile hormone esterase; receptors of the diuretic hormone (helicokinin receptors); stilbene synthase, bibenzyl synthase, chitinases and glucanases. In the plants, these toxins may also be produced as pre-toxins, hybrid proteins or truncated or otherwise modified proteins. Hybrid proteins are characterized by a novel combination of different protein domains (see, for example, WO 2002/015701). Further examples of such toxins or genetically modified plants which produce these toxins are disclosed in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/018810 and WO 03/052073. The methods for producing these genetically modified plants are known to the person skilled in the art and disclosed, for example, in the publications mentioned above. Numerous of the toxins mentioned above bestow, upon the plants by which they are produced, tolerance to pests from all taxonomic classes of arthropods, in particular to beetles (Coeleropta), dipterans (Diptera) and butterflies (Lepidoptera) and to nematodes (Nematoda).


Genetically modified plants which produce one or more genes coding for insecticidal toxins are described, for example, in the publications mentioned above, and some of them are commercially available, such as, for example, YieldGard® (corn varieties producing the toxin Cry1Ab), YieldGard® Plus (corn varieties which produce the toxins Cry1Ab and Cry3Bb1), Star-Link® (corn varieties which produce the toxin Cry9c), Herculex® RW (corn varieties which produce the toxins Cry34Ab1, Cry35Ab1 and the enzyme phosphinothricin-N-acetyltransferase [PAT]); NuCOTN® 33B (cotton varieties which produce the toxin Cry1Ac), Bollgard®I (cotton varieties which produce the toxin Cry1Ac), Bollgard®II (cotton varieties which produce the toxins Cry1Ac and Cry2Ab2); VIPCOT® (cotton varieties which produce a VIP toxin); NewLeaf© (potato varieties which produce the toxin Cry3A); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Bt11 (for example Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France (corn varieties which produce the toxin Cry1Ab and the PAT enzyme), MIR604 from Syngenta Seeds SAS, France (corn varieties which produce a modified version of the toxin Cry3A, see WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium (corn varieties which produce the toxin Cry3Bb1), IPC 531 from Monsanto Europe S.A., Belgium (cotton varieties which produce a modified version of the toxin Cry1Ac) and 1507 from Pioneer Overseas Corporation, Belgium (corn varieties which produce the toxin Cry1F and the PAT enzyme).


Accordingly, the term “crop plants” also includes plants which, with the aid of genetic engineering, produce one or more proteins which are more robust or have increased resistance to bacterial, viral or fungal pathogens, such as, for example, pathogenesis-related proteins (PR proteins, see EP-A 0 392 225), resistance proteins (for example potato varieties producing two resistance genes against Phytophthora infestans from the wild Mexican potato Solanum bulbocastanum) or T4 lysozyme (for example potato cultivars which, by producing this protein, are resistant to bacteria such as Erwinia amylvora).


Accordingly, the term “crop plants” also includes plants whose productivity has been improved with the aid of genetic engineering methods, for example by enhancing the potential yield (for example biomass, grain yield, starch, oil or protein content), tolerance to drought, salt or other limiting environmental factors or resistance to pests and fungal, bacterial and viral pathogens.


The term “crop plants” also includes plants whose ingredients have been modified with the aid of genetic engineering methods in particular for improving human or animal diet, for example by oil plants producing health-promoting long-chain omega 3 fatty acids or monounsaturated omega 9 fatty acids (for example Nexera® oilseed rape).


The term “crop plants” also includes plants which have been modified with the aid of genetic engineering methods for improving the production of raw materials, for example by increasing the amylopectin content of potatoes (Amflora® potato).


Furthermore, it has been found that the compounds of formula I are also suitable for the defoliation and/or desiccation of plant parts, for which crop plants such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton, are suitable. In this regard, there have been found compositions for the desiccation and/or defoliation of plants, processes for preparing these compositions and methods for desiccating and/or defoliating plants using the compounds of formula I.


As desiccants, the compounds of formula I are particularly suitable for desiccating the above-ground parts of crop plants such as potato, oilseed rape, sunflower and soybean, but also cereals. This makes possible the fully mechanical harvesting of these important crop plants.


Also of economic interest is to facilitate harvesting, which is made possible by concentrating within a certain period of time the dehiscence, or reduction of adhesion to the tree, in citrus fruit, olives and other species and varieties of pomaceous fruit, stone fruit and nuts. The same mechanism, i.e. the promotion of the development of abscission tissue between fruit part or leaf part and shoot part of the plants is also essential for the readily controllable defoliation of useful plants, in particular cotton.


Moreover, a shortening of the time interval in which the individual cotton plants mature leads to an increased fiber quality after harvesting.


The compounds of formula I, or the herbicidal compositions comprising the compounds of formula I, can be used, for example, in the form of ready-to-spray aqueous solutions, powders, suspensions, also highly concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for broadcasting, or granules, by means of spraying, atomizing, dusting, spreading, watering or treatment of the seed or mixing with the seed. The use forms depend on the intended purpose; in each case, they should ensure the finest possible distribution of the active ingredients according to the invention.


The herbicidal compositions comprise a herbicidally effective amount of at least one compound of the formula I or an agriculturally useful salt of I, and auxiliaries which are customary for the formulation of crop protection agents.


Examples of auxiliaries customary for the formulation of crop protection agents are inert auxiliaries, solid carriers, surfactants (such as dispersants, protective colloids, emulsifiers, wetting agents and tackifiers), organic and inorganic thickeners, bactericides, antifreeze agents, antifoams, if appropriate colorants and, for seed formulations, adhesives.


Examples of thickeners (i.e. compounds which impart to the formulation modified flow properties, i.e. high viscosity in the state of rest and low viscosity in motion) are polysaccharides, such as xanthan gum (Kelzan® from Kelco), Rhodopol®23 (Rhone Poulenc) or Veegum® (from R.T. Vanderbilt), and also organic and inorganic sheet minerals, such as Attaclay® (from Engelhardt).


Examples of antifoams are silicone emulsions (such as, for example, Silikon® SRE, Wacker or Rhodorsil® from Rhodia), long-chain alcohols, fatty acids, salts of fatty acids, organofluorine compounds and mixtures thereof.


Bactericides can be added for stabilizing the aqueous herbicidal formulation. Examples of bactericides are bactericides based on diclorophen and benzyl alcohol hemiformal (Proxel® from ICI or Acticide® RS from Thor Chemie and Kathon® MK from Rohm & Haas), and also isothiazolinone derivates, such as alkylisothiazolinones and benzisothiazolinones (Acticide MBS from Thor Chemie).


Examples of antifreeze agents are ethylene glycol, propylene glycol, urea or glycerol.


Examples of colorants are both sparingly water-soluble pigments and water-soluble dyes. Examples which may be mentioned are the dyes known under the names Rhodamin B, C.I. Pigment Red 112 and C.I. Solvent Red 1, and also 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 adhesives are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.


Suitable inert auxiliaries are, for example, the following:


mineral oil fractions of medium to high boiling point, such as kerosene and diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example paraffin, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone or strongly polar solvents, for example amines such as N-methylpyrrolidone, and water.


Solid carriers are mineral earths such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate and magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate and ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders, or other solid carriers.


Suitable surfactants (adjuvants, wetting agents, tackifiers, dispersants and also emulsifiers) are the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, for example lignosulfonic acids (e.g. Borrespers-types, Borregaard), phenolsulfonic acids, naphthalenesulfonic acids (Morwet types, Akzo Nobel) and dibutylnaphthalenesulfonic acid (Nekal types, BASF SE), and of fatty acids, alkyl- and alkylarylsulfonates, alkyl sulfates, lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols, and also of fatty alcohol glycol ethers, condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of naphthalene or of the naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl or tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignosulfite waste liquors and proteins, denatured proteins, polysaccharides (e.g. methylcellulose), hydrophobically modified starches, polyvinyl alcohol (Mowiol types Clariant), polycarboxylates (BASF SE, Sokalan types), polyalkoxylates, polyvinylamine (BASF SE, Lupamine types), polyethyleneimine (BASF SE, Lupasol types), polyvinylpyrrolidone and copolymers thereof.


Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active ingredients together with a solid carrier.


Granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers.


Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water. To prepare emulsions, pastes or oil dispersions, the compounds of formula I or Ia, either as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetting agent, tackifier, dispersant or emulsifier. Alternatively, it is also possible to prepare concentrates comprising active substance, wetting agent, tackifier, dispersant or emulsifier and, if desired, solvent or oil, which are suitable for dilution with water.


The concentrations of the compounds of formula I in the ready-to-use preparations can be varied within wide ranges. In general, the formulations comprise from 0.001 to 98% by weight, preferably 0.01 to 95% by weight of at least one active compound. The active compounds are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).


The formulations or ready-to-use preparations may also comprise acids, bases or buffer systems, suitable examples being phosphoric acid or sulfuric acid, or urea or ammonia.


The compounds of formula I of the invention can for example be formulated as follows:


1. Products for Dilution with Water


A. Water-Soluble Concentrates


10 parts by weight of active compound are dissolved in 90 parts by weight of water or a water-soluble solvent. As an alternative, wetters or other adjuvants are added. The active compound dissolves upon dilution with water. This gives a formulation with an active compound content of 10% by weight.


B. Dispersible Concentrates


20 parts by weight of active compound 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. The active compound content is 20% by weight.


C. Emulsifiable Concentrates


15 parts by weight of active compound are dissolved in 75 parts by weight of an organic solvent (e.g. alkylaromatics) with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution with water gives an emulsion. The formulation has an active compound content of 15% by weight.


D. Emulsions


25 parts by weight of active compound are dissolved in 35 parts by weight of an organic solvent (e.g. alkylaromatics) 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 (e.g. Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion. The formulation has an active compound content of 25% by weight.


E. Suspensions


In an agitated ball mill, 20 parts by weight of active compound are comminuted with addition of 10 parts by weight of dispersants and wetters and 70 parts by weight of water or an organic solvent to give a fine active compound suspension. Dilution with water gives a stable suspension of the active compound. The active compound content in the formulation is 20% by weight.


F. Water-Dispersible Granules and Water-Soluble Granules


50 parts by weight of active compound are ground finely with addition of 50 parts by weight of dispersants and wetters and made into 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. The formulation has an active compound content of 50% by weight.


G. Water-Dispersible Powders and Water-Soluble Powders


75 parts by weight of active compound 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. The active compound content of the formulation is 75% by weight.


H. Gel Formulations


In a ball mill, 20 parts by weight of active compound, 10 parts by weight of dispersant, 1 part by weight of gelling agent and 70 parts by weight of water or of an organic solvent are ground to give a fine suspension. Dilution with water gives a stable suspension with active compound content of 20% by weight.


2. Products to be Applied Undiluted


I. Dusts


5 parts by weight of active compound are ground finely and mixed intimately with 95 parts by weight of finely divided kaolin. This gives a dusting powder with an active compound content of 5% by weight.


J. Granules (GR, FG, GG, MG)


0.5 parts by weight of active compound are ground finely and associated with 99.5 parts by weight of carriers. Current methods here are extrusion, spray-drying or the fluidized bed. This gives granules to be applied undiluted with an active compound content of 0.5% by weight.


K. ULV Solutions (UL)


10 parts by weight of active compound are dissolved in 90 parts by weight of an organic solvent, for example xylene. This gives a product to be applied undiluted with an active compound content of 10% by weight.


The compounds of formula I or the herbicidal compositions comprising them can be applied pre- or post-emergence, or together with the seed of a crop plant. It is also possible to apply the herbicidal compositions or active compounds by applying seed, pretreated with the herbicidal compositions or active compounds, of a crop plant. If the active compounds are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that as far as possible they do not come into contact with the leaves of the sensitive crop plants, while the active compounds reach the leaves of undesirable plants growing underneath, or the bare soil surface (post-directed, lay-by).


In a further embodiment, the compounds of formula I or the herbicidal compositions can be applied by treating seed.


The treatment of seed comprises essentially all procedures familiar to the person skilled in the art (seed dressing, seed coating, seed dusting, seed soaking, seed film coating, seed multi-layer coating, seed encrusting, seed dripping and seed pelleting) based on the compounds of formula I according to the invention or the compositions prepared therefrom. Here, the herbicidal compositions can be applied diluted or undiluted.


The term seed comprises seed of all types, such as, for example, corns, seeds, fruits, tubers, cuttings and similar forms. Here, preferably, the term seed describes corns and seeds.


The seed used can be seed of the useful plants mentioned above, but also the seed of transgenic plants or plants obtained by customary breeding methods.


The rates of application of active compound are from 0.001 to 3.0, preferably 0.01 to 1.0, kg/ha of active substance (a.s.), depending on the control target, the season, the target plants and the growth stage. To treat the seed, the compounds of formula I are generally employed in amounts of from 0.001 to 10 kg per 100 kg of seed.


It may also be advantageous to use the compounds of formula I in combination with safeners, also termed herbicide safeners. Safeners are chemical compounds which prevent or re-duce damage to useful plants without substantially affecting the herbicidal action of the compounds of formula I on unwanted plants. They can be used both before sowing (for example in the treatment of seed, or on cuttings or seedlings) and before or after the emergence of the useful plant. The safeners and the compounds of formula I can be used simultaneously or in succession.


Suitable safeners are, for example, (quinolin-8-oxy)acetic acids, 1-phenyl-5-haloalkyl-1H-1,2,4-triazole-3-carboxylic acids, 1-phenyl-4,5-dihydro-5-alkyl-1H-pyrazole-3,5-dicarboxylic acids, 4,5-dihydro-5,5-diaryl-3-isoxazolecarboxylic acids, dichloroacetamides, alpha-oximinophenylacetonitriles, acetophenone oximes, 4,6-dihalo-2-phenylpyrimidines, N-[[4-(aminocarbonyl)phenyl]sulfonyl]-2-benzamides, 1,8-naphthalic anhydride, 2-halo-4-(haloalkyl)-5-thiazolecarboxylic acids, phosphorothiolates and O-phenyl N-alkylcarbamates and their agriculturally useful salts and, provided that they have an acid function, their agriculturally useful derivatives, such as amides, esters and thioesters.


To broaden the activity spectrum and to obtain synergistic effects, the compounds of the formula I can be mixed and jointly applied with numerous representatives of other compounds having herbicidal activity (herbicides B) or growth-regulating activity, optionally in combination with safeners. Suitable mixing partners are, for example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives, aminotriazoles, anilides, aryloxy/heteroaryl-oxyalkanoic acids and their derivatives, benzoic acid and its derivatives, benzothiadiazinones, 2-(hetaroyl/aroyl)-1,3-cyclohexanediones, heteroaryl aryl ketones, benzylisoxazolidinones, meta-CF3-phenyl derivatives, carbamates, quinoline carboxylic acid and its derivatives, chloro-acetanilides, cyclohexenone oxime ether derivates, diazines, dichloropropionic acid and its derivatives, dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- and heteroaryloxyphenoxypropionic esters, phenylacetic acid and its derivatives, 2-phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridine-carboxylic acid and its derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides, uracils and also phenylpyrazolines and isoxazolines and their derivatives.


Moreover, it may be useful to apply the compounds of formula I alone or in combination with other herbicides B or else also mixed with further crop protection agents, jointly, for example with compositions for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions which are employed for alleviating nutritional and trace element deficiencies. Other additives such as nonphytotoxic oils and oil concentrates may also be added.


Examples of herbicides B which can be used in combination with the benzamide compounds of formula I according to the present invention are:


b1) from the group of the lipid biosynthesis inhibitors:


alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim, 4-(4′-Chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-72-6); 4-(2′,4′-Dichloro-4-cyclopropyl[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-45-3); 4-(4′-Chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1033757-93-5); 4-(2′,4′-Dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione (CAS 1312340-84-3); 5-(Acetyloxy)-4-(4′-chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312337-48-6); 5-(Acetyloxy)-4-(2′,4′-dichloro-4-cyclopropyl-[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one; 5-(Acetyloxy)-4-(4′-chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312340-82-1); 5-(Acetyloxy)-4-(2′,4′-dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1033760-55-2); 4-(4′-Chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312337-51-1); 4-(2′,4′-Dichloro-4-cyclopropyl-[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester; 4-(4′-Chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312340-83-2); 4-(2′,4′-Dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1033760-58-5), benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, tiocarbazil, triallate and vernolate;


b2) from the group of the ALS inhibitors:


amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, bispyribac, bispyribac-sodium, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cloransulam, cloransulam-methyl, cyclosulfamuron, diclosulam, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone, flucarbazone-sodium, flucetosulfuron, flumetsulam, flupyrsulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, mesosulfuron, metosulam, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, penoxsulam, primisulfuron, primisulfuron-methyl, propoxycarbazone, propoxycarbazone-sodium, prosulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, pyrimisulfan, pyriftalid, pyriminobac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, pyroxsulam, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron, triflusulfuron-methyl and tritosulfuron;


b3) from the group of the photosynthesis inhibitors:


ametryn, amicarbazone, atrazine, bentazone, bentazone-sodium, bromacil, bromofenoxim, bromoxynil and its salts and esters, chlorobromuron, chloridazone, chlorotoluron, chloroxuron, cyanazine, desmedipham, desmetryn, dimefuron, dimethametryn, diquat, diquat-dibromide, diuron, fluometuron, hexazinone, ioxynil and its salts and esters, isoproturon, isouron, karbutilate, lenacil, linuron, metamitron, methabenzthiazuron, metobenzuron, metoxuron, metribuzin, monolinuron, neburon, paraquat, paraquat-dichloride, paraquat-dimetilsulfate, pentanochlor, phenmedipham, phenmedipham-ethyl, prometon, prometryn, propanil, propazine, pyridafol, pyridate, siduron, simazine, simetryn, tebuthiuron, terbacil, terbumeton, terbuthylazine, terbutryn, thidiazuron, trietazine, 1-(6-tert-butylpyrimidin-4-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1654744-66-7), 1-(5-tert-butylisoxazol-3-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455-12-9), 1-(5-tert-butylisoxazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1637453-94-1), 1-(5-tert-butyl-1-methyl-pyrazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1654057-29-0), 1-(5-tert-butyl-1-methyl-pyrazol-3-yl)-3-chloro-2-hydroxy-4-methyl-2H-pyrrol-5-one (CAS 1654747-80-4), 4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one; (CAS 2023785-78-4), 4-hydroxy-1,5-dimethyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 2023785-79-5), 5-ethoxy-4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1701416-69-4), 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1708087-22-2), 4-hydroxy-1,5-dimethyl-3-[1-methyl-5-(trifluoromethyl)pyrazol-3-yl]imidazolidin-2-one (CAS 2023785-80-8) and 1-(5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidin-2-one (CAS 1844836-64-1);


b4) from the group of the protoporphyrinogen-IX oxidase inhibitors:


acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, 2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H-pyrimidinyl]-4-fluoro-N-[(isopropyl)methylsulfamoyl]benzamide (H-1; CAS 372137-35-4), ethyl [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (H-2; CAS 353292-31-6), N-ethyl-3-(2,6-dichloro-4-trifluoro-methylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (H-3; CAS 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (H-4; CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (H-5; CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (H-6; CAS 45100-03-7), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione (CAS 451484-50-7), 1,5-dimethyl-6-thioxo-3-(2,2,7-trifluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-1,3,5-triazinane-2,4-dione (trifludimoxazin), 2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1,3-dione (CAS 1300118-96-0), 1-methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione (CAS 1304113-05-0), methyl (E)-4-[2-chloro-5-[4-chloro-5-(difluoromethoxy)-1H-methyl-pyrazol-3-yl]-4-fluoro-phenoxy]-3-methoxy-but-2-enoate (CAS 948893-00-3), and 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione (CAS 212754-02-4);


b5) from the group of the bleacher herbicides:


aclonifen, amitrol, beflubutamid, benzobicyclon, benzofenap, clomazone, diflufenican, fenquinotrione, flumeturon, fluridone, flurochloridone, flurtamone, isoxaflutole, mesotrione, norflurazon, oxotrione (CAS 1486617-21-3), picolinafen, pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone, 4-hydroxy-3-[[2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)-3-pyridyl]carbonyl]bicyclo[3.2.1]oct-3-en-2-one (H-7; CAS 352010-68-5, bicyclopyrone), 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)-pyrimidine (H-8; CAS 180608-33-7) -chloro-3-methylsulfanyl-N-(1-methyltetrazol-5-yl)-4-(trifluoromethyl)benzamide (CAS 1361139-71-0), 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone (CAS 81777-95-9) and 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone (CAS 81778-66-7);


b6) from the group of the EPSP synthase inhibitors:


glyphosate, glyphosate-isopropylammonium and glyphosate-trimesium (sulfosate);


b7) from the group of the glutamine synthase inhibitors:


bilanaphos (bialaphos), bilanaphos-sodium, glufosinate and glufosinate-ammonium;


b8) from the group of the DHP synthase inhibitors:


asulam;


b9) from the group of the mitose inhibitors:


amiprophos, amiprophos-methyl, benfluralin, butamiphos, butralin, carbetamide, chlorpropham, chlorthal, chlorthal-dimethyl, dinitramine, dithiopyr, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine, propham, propyzamide, tebutam, thiazopyr and trifluralin;


b10) from the group of the VLCFA inhibitors:


acetochlor, alachlor, anilofos, butachlor, cafenstrole, dimethachlor, dimethanamid, dimethenamid-P, diphenamid, fentrazamide, flufenacet, mefenacet, metazachlor, metolachlor, metolachlor-S, naproanilide, napropamide, pethoxamid, piperophos, pretilachlor, propachlor, propisochlor, pyroxasulfone (KIH-485) and thenylchlor; Compounds of the formula 2:




embedded image


in which the variables have the following meanings:


Y is phenyl or 5- or 6-membered heteroaryl as defined at the outset, which radicals may be substituted by one to three groups Raa; R21, R22, R23, R24 are H, halogen or C1-C4-alkyl; X is O or NH; N is 0 or 1.


Compounds of the formula 2 have in particular the following meanings:


Y is




embedded image


where # denotes the bond to the skeleton of the molecule; and


R21, R22, R23, R24 are H, Cl, F or CH3; R25 is halogen, C1-C4-alkyl or C1-C4-haloalkyl; R26 is C1-C4-alkyl; R27 is halogen, C1-C4-alkoxy or C1-C4-haloalkoxy; R28 is H, halogen, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-haloalkoxy; M is 0, 1, 2 or 3; X is oxygen; N is 0 or 1.


Preferred compounds of the formula 2 have the following meanings:


Y is




embedded image


R21 is H; R22, R23 are F; R24 is H or F; X is oxygen; N is 0 or 1.


Particularly preferred compounds of the formula 2 are:


3-[5-(2,2-difluoroethoxy)-1-methyl-3-trifluoromethyl-1H-pyrazol-4-ylmethane-sulfonyl]-4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole (2-1); 3-{[5-(2,2-difluoroethoxy)-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl]fluoromethanesulfonyl}-5,5-dimethyl-4,5-dihydroisoxazole (2-2); 4-(4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonylmethyl)-2-methyl-5-trifluoromethyl-2H-[1,2,3]triazole (2-3); 4-[(5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonyl)fluoromethyl]-2-methyl-5-trifluoromethyl-2H-[1,2,3]triazole (2-4); 4-(5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonylmethyl)-2-methyl-5-trifluoromethyl-2H-[1,2,3]triazole (2-5); 3-{[5-(2,2-difluoroethoxy)-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl]difluoromethanesulfonyl}-5,5-dimethyl-4,5-dihydroisoxazole (2-6); 4-[(5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonyl)difluoromethyl]-2-methyl-5-trifluoromethyl-2H-[1,2,3]triazole (2-7); 3-{[5-(2,2-difluoroethoxy)-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl]difluoromethanesulfonyl}-4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole (2-8); 4-[difluoro-(4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonyl)methyl]-2-methyl-5-trifluoromethyl-2H-[1,2,3]triazole (2-9);


b11) from the group of the cellulose biosynthesis inhibitors:


chlorthiamid, dichlobenil, flupoxam and isoxaben;


b12) from the group of the decoupler herbicides:


dinoseb, dinoterb and DNOC and its salts;


b13) from the group of the auxin herbicides:


2,4-D and its salts and esters, 2,4-DB and its salts and esters, aminopyralid and its salts such as aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifen and its salts and esters, MCPA and its salts and esters, MCPA-thioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, TBA (2,3,6) and its salts and esters, triclopyr and its salts and esters, 5,6-dichloro-2-cyclopropyl-4-pyrimidinecarboxylic acid (H-9; CAS 858956-08-8) and its salts and esters, florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661-72-9) and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)picolinic acid (CAS 1629965-65-6);


b14) from the group of the auxin transport inhibitors: diflufenzopyr, diflufenzopyr-sodium, naptalam and naptalam-sodium;


b15) from the group of the other herbicides: bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, maleic hydrazide, mefluidide, metam, methyl azide, methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine, triaziflam, tridiphane and 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (H-10; CAS 499223-49-3) and its salts and esters.


Examples of preferred safeners C are benoxacor, cloquintocet, cyometrinil, cyprosulfamide, dichlormid, dicyclonone, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, mephenate, naphthalic anhydride, oxabetrinil, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (H-11; MON4660, CAS 71526-07-3) and 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (H-12; R-29148, CAS 52836-31-4).


The active compounds of groups b1) to b15) and the safeners C are known herbicides and safeners, see, for example, The Compendium of Pesticide Common Names (http://www.alanwood.net/pesticides/); B. Hock, C. Fedtke, R. R. Schmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart, 1995. Further herbicidally active compounds are known from WO 96/26202, WO 97/41116, WO 97/41117, WO 97/41118, WO 01/83459 and WO 2008/074991 and from W. Krämer et al. (ed.) “Modern Crop Protection Compounds”, Vol. 1, Wiley VCH, 2007 and the literature quoted therein.


The invention also relates to combinations comprising at least one benzamide compound of the formula I and at least one further active compound, in particular a compound having herbicide activity (herbicide B) preferably selected from the active compounds of groups b1 to b15, and/or a safener C.


The invention also relates to compositions in the form of a crop protection composition formulated as a 1-component composition comprising an active compound combination comprising at least one benzamide compound of the formula I and at least one further active compound, in particular a compound having herbicide activity (herbicide B) preferably selected from the active compounds of groups b1 to b15, and at least one solid or liquid carrier and/or one or more surfactants and, if desired, one or more further auxiliaries customary for crop protection compositions.


The invention also relates to compositions in the form of a crop protection composition formulated as a 1-component composition comprising an active compound combination comprising at least one benzamide compound of the formula I and at least one safener C and at least one solid or liquid carrier and/or one or more surfactants and, if desired, one or more further auxiliaries customary for crop protection compositions.


The invention also relates to compositions in the form of a crop protection composition formulated as a 1-component composition comprising an active compound combination comprising at least one benzamide compound of the formula I and at least one further active compound, in particular a compound having herbicide activity (herbicide B) which is preferably selected from the active compounds of groups b1 to b15, a safener C and at least one solid or liquid carrier and/or one or more surfactants and, if desired, one or more further auxiliaries customary for crop protection compositions.


The invention also relates to compositions in the form of a crop protection composition formulated as a 2-component composition comprising a first component comprising at least one compound of the formula I, a solid or liquid carrier and/or one or more surfactants and a second component comprising at least one further active compound, in particular a compound having herbicide activity (herbicide B) which is preferably selected from the active compounds of groups b1 to b15, a solid or liquid carrier and/or one or more surfactants, where additionally both components may also comprise further auxiliaries customary for crop protection compositions.


The invention also relates to compositions in the form of a crop protection composition formulated as a 2-component composition comprising a first component comprising at least one compound of the formula I, a solid or liquid carrier and/or one or more surfactants and a second component comprising at least one further active compound, in particular a compound having herbicide activity (herbicide B) which is preferably selected from the active compounds of groups b1 to b15, a solid or liquid carrier and/or one or more surfactants, where additionally both components may also comprise further auxiliaries customary for crop protection compositions, where the first component or the second component further comprises a safener C.


In binary compositions comprising at least one compound of the formula I as component A and at least one herbicide B, the weight ratio of the active compounds A:B is generally in the range of from 1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, in particular in the range of from 1:250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1.


In binary compositions comprising at least one compound of the formula I as component A and at least one safener C, the weight ratio of the active compounds A:C is generally in the range of from 1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, in particular in the range of from 1:250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1.


In ternary compositions comprising both at least one compound of the formula I as component A, at least one herbicide B and at least one safener C, the relative parts by weight of the components A:B are generally in the range of from 1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, in particular in the range of from 1:250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1; the weight ratio of the components A:C is generally in the range of from 1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, in particular in the range of from 1:250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1; and the weight ratio of the components B:C is generally in the range of from 1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, in particular in the range of from 1:250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1. Preferably, the weight ratio of the components A+B to the component C is in the range of from 1:500 to 500:1, in particular in the range of from 1:250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1.


Examples of particularly preferred compositions according to the invention comprising in each case one individualized compound of the formula I and one mixing partner or a mixing partner combination are given in Table B below.


A further aspect of the invention relates to the combinations B-1 to B-1406 listed in Table B below, where in each case one row of Table B corresponds to a herbicidal composition comprising one of the compounds of formula I individualized in the above description (component 1) and the further active compound from groups b1) to b15) and/or safener C stated in each case in the row in question (component 2). The active compounds in the combinations described are in each case preferably present in synergistically effective amounts.


Amongst these compositions B-1 to B-1406 a particular group of embodiments relates to combinations B-1.1 to B-1406.1, where the compound of formula (I) is 4-bromo-6-fluoro-2-methyl-N-(1-methyltetrazol-5-yl)-3-[[methyl(2,2,2-trifluoroethyl)carbamoyl]amino]benzamide and where the further active compound from groups b1) to b15) and/or safener C stated in each case in the row in question.


Amongst these compositions B-1 to B-1406 another particular group of embodiments relates to combinations B-1.2 to B-1406.2, where the compound of formula (1) is 4-bromo-6-fluoro-2-methyl-N-(1-methyltetrazol-5-yl)-3-[[ethyl(2,2,2-trifluoroethyl)carbamoyl]-amino]benzamide and where the further active compound from groups b) to b15) and/or safener C stated in each case in the row in question.


Amongst these compositions B-1 to B-1406 a further particular group of embodiments relates to combinations B-1.3 to B-1406.3, where the compound of formula (I) is 2,4-dichloro-6-fluoro-N-(1-methyltetrazol-5-yl)-3-[[methyl (2,2,2-trifluoroethyl)carbamoyl]amino]benzamide and where the further active compound from groups b1) to b15) and/or safener C stated in each case in the row in question.











TABLE B






Herbicide(s) B
Safener C







B-1
clodinafop-propargyl
—


B-2
cycloxydim
—


B-3
cyhalofop-butyl
—


B-4
fenoxaprop-P-ethyl
—


B-5
pinoxaden
—


B-6
profoxydim
—


B-7
tepraloxydim
—


B-8
tralkoxydim
—


B-9
esprocarb
—


B-10
prosulfocarb
—


B-11
thiobencarb
—


B-12
triallate
—


B-13
bensulfuron-methyl
—


B-14
bispyribac-sodium
—


B-15
cyclosulfamuron
—


B-16
flumetsulam
—


B-17
flupyrsulfuron-methyl-sodium
—


B-18
foramsulfuron
—


B-19
imazamox
—


B-20
imazapic
—


B-21
imazapyr
—


B-22
imazaquin
—


B-23
imazethapyr
—


B-24
imazosulfuron
—


B-25
iodosulfuron-methyl-sodium
—


B-26
mesosulfuron
—


B-27
nicosulfuron
—


B-28
penoxsulam
—


B-29
propoxycarbazone-sodium
—


B-30
pyrazosulfuron-ethyl
—


B-31
pyroxsulam
—


B-32
rimsulfuron
—


B-33
sulfosulfuron
—


B-34
thiencarbazone-methyl
—


B-35
tritosulfuron
—


B-36
2,4-D and its salts and esters
—


B-37
aminopyralid and its salts and esters
—


B-38
clopyralid and its salts and esters
—


B-39
dicamba and its salts and esters
—


B-40
fluroxypyr-meptyl
—


B-41
quinclorac
—


B-42
quinmerac
—


B-43
H-9
—


B-44
diflufenzopyr
—


B-45
diflufenzopyr-sodium
—


B-46
clomazone
—


B-47
diflufenican
—


B-48
fluorochloridone
—


B-49
isoxaflutol
—


B-50
mesotrione
—


B-51
picolinafen
—


B-52
sulcotrione
—


B-53
tefuryltrione
—


B-54
tembotrione
—


B-55
topramezone
—


B-56
H-7
—


B-57
atrazine
—


B-58
diuron
—


B-59
fluometuron
—


B-60
hexazinone
—


B-61
isoproturon
—


B-62
metribuzin
—


B-63
propanil
—


B-64
terbuthylazine
—


B-65
paraquat dichloride
—


B-66
flumioxazin
—


B-67
oxyfluorfen
—


B-68
saflufenacil
—


B-69
sulfentrazone
—


B-70
H-1
—


B-71
H-2
—


B-72
glyphosate
—


B-73
glyphosate-isopropylammonium
—


B-74
glyphosate-trimesium (sulfosate)
—


B-75
glufosinate
—


B-76
glufosinate-ammonium
—


B-77
pendimethalin
—


B-78
trifluralin
—


B-79
acetochlor
—


B-80
cafenstrole
—


B-81
dimethenamid-P
—


B-82
fentrazamide
—


B-83
flufenacet
—


B-84
mefenacet
—


B-85
metazachlor
—


B-86
metolachlor-S
—


B-87
pyroxasulfone
—


B-88
isoxaben
—


B-89
dymron
—


B-90
indanofan
—


B-91
oxaziclomefone
—


B-92
triaziflam
—


B-93
chlorotoluron
—


B-94
pinoxaden
—


B-95
sethoxydim
—


B-96
clethodim
—


B-97
diclofop
—


B-98
quizalofop
—


B-99
thifensulfuron
—


B-100
tribenuron
—


B-101
metsulfuron
—


B-102
foramsulfuron
—


B-103
chlorimuron
—


B-104
chlorsulfuron
—


B-105
flucarbazone-sodium
—


B-106
propoxycarbazone-sodium
—


B-107
ethalfluralin
—


B-108
halauxifen
—


B-109
MCPA
—


B-110
bromoxynil
—


B-111
bentazone
—


B-112
carfentrazone
—


B-113
trifludimoxazin
—


B-114
bicyclopyrone
—


B-115
benzobicyclon
—


B-116
pyrasulfotole
—


B-117
diquat
—


B-118
cinmethylin
—


B-119
acetochlor
—


B-120
naptalam
—


B-121
atrazine + H-1
—


B-122
atrazine + glyphosate
—


B-123
atrazine + mesotrione
—


B-124
atrazine + nicosulfuron
—


B-125
atrazine + tembotrione
—


B-126
atrazine + topramezone
—


B-127
clomazone + glyphosate
—


B-128
diflufenican + clodinafop-propargyl
—


B-129
diflufenican + fenoxaprop-P-ethyl
—


B-130
diflufenican + flupyrsulfuron-methyl-sodium
—


B-131
diflufenican + glyphosate
—


B-132
diflufenican + mesosulfuron-methyl
—


B-133
diflufenican + pinoxaden
—


B-134
diflufenican + pyroxsulam
—


B-135
flumetsulam + glyphosate
—


B-136
flumioxazin + glyphosate
—


B-137
imazapic + glyphosate
—


B-138
imazethapyr + glyphosate
—


B-139
isoxaflutol + H-1
—


B-140
isoxaflutol + glyphosate
—


B-141
metazachlor + H-1
—


B-142
metazachlor + glyphosate
—


B-143
metazachlor + mesotrione
—


B-144
metazachlor + nicosulfuron
—


B-145
metazachlor + terbuthylazine
—


B-146
metazachlor + topramezone
—


B-147
metribuzin + glyphosate
—


B-148
pendimethalin + H-1
—


B-149
pendimethalin + clodinafop-propargyl
—


B-150
pendimethalin + fenoxaprop-P-ethyl
—


B-151
pendimethalin + flupyrsulfuron-methyl-
—



sodium



B-152
pendimethalin + glyphosate
—


B-153
pendimethalin + mesosulfuron-methyl
—


B-154
pendimethalin + mesotrione
—


B-155
pendimethalin + nicosulfuron
—


B-156
pendimethalin + pinoxaden
—


B-157
pendimethalin + pyroxsulam
—


B-158
pendimethalin + tembotrione
—


B-159
pendimethalin + topramezone
—


B-160
pyroxasulfone + tembotrione
—


B-161
pyroxasulfone + topramezone
—


B-162
sulfentrazone + glyphosate
—


B-163
terbuthylazine + H-1
—


B-164
terbuthylazine + foramsulfuron
—


B-165
terbuthylazine + glyphosate
—


B-166
terbuthylazine + mesotrione
—


B-167
terbuthylazine + nicosulfuron
—


B-168
terbuthylazine + tembotrione
—


B-169
terbuthylazine + topramezone
—


B-170
trifluralin + glyphosate
—


B-171
—
benoxacor


B-172
—
cloquintocet


B-173
—
cyprosulfamide


B-174
—
dichlormid


B-175
—
fenchlorazole


B-176
—
fenclorim


B-177
—
isoxadifen


B-178
—
mefenpyr


B-179
—
H-11


B-180
—
H-12


B-181
clodinafop-propargyl
benoxacor


B-182
cycloxydim
benoxacor


B-183
cyhalofop-butyl
benoxacor


B-184
fenoxaprop-P-ethyl
benoxacor


B-185
pi noxaden
benoxacor


B-186
profoxydim
benoxacor


B-187
tepraloxydim
benoxacor


B-188
tralkoxydim
benoxacor


B-189
esprocarb
benoxacor


B-190
prosulfocarb
benoxacor


B-191
thiobencarb
benoxacor


B-192
triallate
benoxacor


B-193
bensulfuron-methyl
benoxacor


B-194
bispyribac-sodium
benoxacor


B-195
cyclosulfamuron
benoxacor


B-196
flumetsulam
benoxacor


B-197
flupyrsulfuron-methyl-sodium
benoxacor


B-198
foramsulfuron
benoxacor


B-199
imazamox
benoxacor


B-200
imazapic
benoxacor


B-201
imazapyr
benoxacor


B-202
imazaquin
benoxacor


B-203
imazethapyr
benoxacor


B-204
imazosulfuron
benoxacor


B-205
iodosulfuron-methyl-sodium
benoxacor


B-206
mesosulfuron
benoxacor


B-207
nicosulfuron
benoxacor


B-208
penoxsulam
benoxacor


B-209
propoxycarbazone-sodium
benoxacor


B-210
pyrazosulfuron-ethyl
benoxacor


B-211
pyroxsulam
benoxacor


B-212
rimsulfuron
benoxacor


B-213
sulfosulfuron
benoxacor


B-214
thiencarbazone-methyl
benoxacor


B-215
tritosulfuron
benoxacor


B-216
2,4-D and its salts and esters
benoxacor


B-217
aminopyralid and its salts and esters
benoxacor


B-218
clopyralid and its salts and esters
benoxacor


B-219
dicamba and its salts and esters
benoxacor


B-220
fluroxypyr-meptyl
benoxacor


B-221
quinclorac
benoxacor


B-222
quinmerac
benoxacor


B-223
H-9
benoxacor


B-224
diflufenzopyr
benoxacor


B-225
diflufenzopyr-sodium
benoxacor


B-226
clomazone
benoxacor


B-227
diflufenican
benoxacor


B-228
fluorochloridone
benoxacor


B-229
isoxaflutol
benoxacor


B-230
mesotrione
benoxacor


B-231
picolinafen
benoxacor


B-232
sulcotrione
benoxacor


B-233
tefuryltrione
benoxacor


B-234
tembotrione
benoxacor


B-235
topramezone
benoxacor


B-236
H-7
benoxacor


B-237
atrazine
benoxacor


B-238
diuron
benoxacor


B-239
fluometuron
benoxacor


B-240
hexazinone
benoxacor


B-241
isoproturon
benoxacor


B-242
metribuzin
benoxacor


B-243
propanil
benoxacor


B-244
terbuthylazine
benoxacor


B-245
paraquat dichloride
benoxacor


B-246
flumioxazin
benoxacor


B-247
oxyfluorfen
benoxacor


B-248
saflufenacil
benoxacor


B-249
sulfentrazone
benoxacor


B-250
H-1
benoxacor


B-251
H-2
benoxacor


B-252
glyphosate
benoxacor


B-253
glyphosate-isopropylammonium
benoxacor


B-254
glyphosate-trimesium (sulfosate)
benoxacor


B-255
glufosinate
benoxacor


B-256
glufosinate-ammonium
benoxacor


B-257
pendimethalin
benoxacor


B-258
trifluralin
benoxacor


B-259
acetochlor
benoxacor


B-260
cafenstrole
benoxacor


B-261
dimethenamid-P
benoxacor


B-262
fentrazamide
benoxacor


B-263
flufenacet
benoxacor


B-264
mefenacet
benoxacor


B-265
metazachlor
benoxacor


B-266
metolachlor-S
benoxacor


B-267
pyroxasulfone
benoxacor


B-268
isoxaben
benoxacor


B-269
dymron
benoxacor


B-270
indanofan
benoxacor


B-271
oxaziclomefone
benoxacor


B-272
triaziflam
benoxacor


B-273
atrazine + H-1
benoxacor


B-274
atrazine + glyphosate
benoxacor


B-275
atrazine + mesotrione
benoxacor


B-276
atrazine + nicosulfuron
benoxacor


B-277
atrazine + tembotrione
benoxacor


B-278
atrazine + topramezone
benoxacor


B-279
clomazone + glyphosate
benoxacor


B-280
diflufenican + clodinafop-propargyl
benoxacor


B-281
diflufenican + fenoxaprop-P-ethyl
benoxacor


B-282
diflufenican + flupyrsulfuron-methyl-sodium
benoxacor


B-283
diflufenican + glyphosate
benoxacor


B-284
diflufenican + mesosulfuron-methyl
benoxacor


B-285
diflufenican + pinoxaden
benoxacor


B-286
diflufenican + pyroxsulam
benoxacor


B-287
flumetsulam + glyphosate
benoxacor


B-288
flumioxazin + glyphosate
benoxacor


B-289
imazapic + glyphosate
benoxacor


B-290
imazethapyr + glyphosate
benoxacor


B-291
isoxaflutol + H-1
benoxacor


B-292
isoxaflutol + glyphosate
benoxacor


B-293
metazachlor + H-1
benoxacor


B-294
metazachlor + glyphosate
benoxacor


B-295
metazachlor + mesotrione
benoxacor


B-296
metazachlor + nicosulfuron
benoxacor


B-297
metazachlor + terbuthylazine
benoxacor


B-298
metazachlor + topramezone
benoxacor


B-299
metribuzin + glyphosate
benoxacor


B-300
pendimethalin + H-1
benoxacor


B-301
pendimethalin + clodinafop-propargyl
benoxacor


B-302
pendimethalin + fenoxaprop-P-ethyl
benoxacor


B-303
pendimethalin + flupyrsulfuron-methyl-sodium
benoxacor


B-304
pendimethalin + glyphosate
benoxacor


B-305
pendimethalin + mesosulfuron-methyl
benoxacor


B-306
pendimethalin + mesotrione
benoxacor


B-307
pendimethalin + nicosulfuron
benoxacor


B-308
pendimethalin + pinoxaden
benoxacor


B-309
pendimethalin + pyroxsulam
benoxacor


B-310
pendimethalin + tembotrione
benoxacor


B-311
pendimethalin + topramezone
benoxacor


B-312
pyroxasulfone + tembotrione
benoxacor


B-313
pyroxasulfone + topramezone
benoxacor


B-314
sulfentrazone + glyphosate
benoxacor


B-315
terbuthylazine + H-1
benoxacor


B-316
terbuthylazine + foramsulfuron
benoxacor


B-317
terbuthylazine + glyphosate
benoxacor


B-318
terbuthylazine + mesotrione
benoxacor


B-319
terbuthylazine + nicosulfuron
benoxacor


B-320
terbuthylazine + tembotrione
benoxacor


B-321
terbuthylazine + topramezone
benoxacor


B-322
trifluralin + glyphosate
benoxacor


B-323
clodinafop-propargyl
cloquintocet


B-324
cycloxydim
cloquintocet


B-325
cyhalofop-butyl
cloquintocet


B-326
fenoxaprop-P-ethyl
cloquintocet


B-327
pinoxaden
cloquintocet


B-328
profoxydim
cloquintocet


B-329
tepraloxydim
cloquintocet


B-330
tralkoxydim
cloquintocet


B-331
esprocarb
cloquintocet


B-332
prosulfocarb
cloquintocet


B-333
thiobencarb
cloquintocet


B-334
triallate
cloquintocet


B-335
bensulfuron-methyl
cloquintocet


B-336
bispyribac-sodium
cloquintocet


B-337
cyclosulfamuron
cloquintocet


B-338
flumetsulam
cloquintocet


B-339
flupyrsulfuron-methyl-sodium
cloquintocet


B-340
foramsulfuron
cloquintocet


B-341
imazamox
cloquintocet


B-342
imazapic
cloquintocet


B-343
imazapyr
cloquintocet


B-344
imazaquin
cloquintocet


B-345
imazethapyr
cloquintocet


B-346
imazosulfuron
cloquintocet


B-347
iodosulfuron-methyl-sodium
cloquintocet


B-348
mesosulfuron
cloquintocet


B-349
nicosulfuron
cloquintocet


B-350
penoxsulam
cloquintocet


B-351
propoxycarbazone-sodium
cloquintocet


B-352
pyrazosulfuron-ethyl
cloquintocet


B-353
pyroxsulam
cloquintocet


B-354
rimsulfuron
cloquintocet


B-355
sulfosulfuron
cloquintocet


B-356
thiencarbazone-methyl
cloquintocet


B-357
tritosulfuron
cloquintocet


B-358
2,4-D and its salts and esters
cloquintocet


B-359
aminopyralid and its salts and esters
cloquintocet


B-360
clopyralid and its salts and esters
cloquintocet


B-361
dicamba and its salts and esters
cloquintocet


B-362
fluroxypyr-meptyl
cloquintocet


B-363
quinclorac
cloquintocet


B-364
quinmerac
cloquintocet


B-365
H-9
cloquintocet


B-366
diflufenzopyr
cloquintocet


B-367
diflufenzopyr-sodium
cloquintocet


B-368
clomazone
cloquintocet


B-369
diflufenican
cloquintocet


B-370
fluorochloridone
cloquintocet


B-371
isoxaflutol
cloquintocet


B-372
mesotrione
cloquintocet


B-373
picolinafen
cloquintocet


B-374
sulcotrione
cloquintocet


B-375
tefuryltrione
cloquintocet


B-376
tembotrione
cloquintocet


B-377
topramezone
cloquintocet


B-378
H-7
cloquintocet


B-379
atrazine
cloquintocet


B-380
diuron
cloquintocet


B-381
fluometuron
cloquintocet


B-382
hexazinone
cloquintocet


B-383
isoproturon
cloquintocet


B-384
metribuzin
cloquintocet


B-385
propanil
cloquintocet


B-386
terbuthylazine
cloquintocet


B-387
paraquat dichloride
cloquintocet


B-388
flumioxazin
cloquintocet


B-389
oxyfluorfen
cloquintocet


B-390
saflufenacil
cloquintocet


B-391
sulfentrazone
cloquintocet


B-392
H-1
cloquintocet


B-393
H-2
cloquintocet


B-394
glyphosate
cloquintocet


B-395
glyphosate-isopropylammonium
cloquintocet


B-396
glyphosate-trimesium (sulfosate)
cloquintocet


B-397
glufosinate
cloquintocet


B-398
glufosinate-ammonium
cloquintocet


B-399
pendimethalin
cloquintocet


B-400
trifluralin
cloquintocet


B-401
acetochlor
cloquintocet


B-402
cafenstrole
cloquintocet


B-403
dimethenamid-P
cloquintocet


B-404
fentrazamide
cloquintocet


B-405
flufenacet
cloquintocet


B-406
mefenacet
cloquintocet


B-407
metazachlor
cloquintocet


B-408
metolachlor-S
cloquintocet


B-409
pyroxasulfone
cloquintocet


B-410
isoxaben
cloquintocet


B-411
dymron
cloquintocet


B-412
indanofan
cloquintocet


B-413
oxaziclomefone
cloquintocet


B-414
triaziflam
cloquintocet


B-415
atrazine + H-1
cloquintocet


B-416
atrazine + glyphosate
cloquintocet


B-417
atrazine + mesotrione
cloquintocet


B-418
atrazine + nicosulfuron
cloquintocet


B-419
atrazine + tembotrione
cloquintocet


B-420
atrazine + topramezone
cloquintocet


B-421
clomazone + glyphosate
cloquintocet


B-422
diflufenican + clodinafop-propargyl
cloquintocet


B-423
diflufenican + fenoxaprop-p-ethyl
cloquintocet


B-424
diflufenican + flupyrsulfuron-methyl-sodium
cloquintocet


B-425
diflufenican + glyphosate
cloquintocet


B-426
diflufenican + mesosulfuron-methyl
cloquintocet


B-427
diflufenican + pinoxaden
cloquintocet


B-428
diflufenican + pyroxsulam
cloquintocet


B-429
flumetsulam + glyphosate
cloquintocet


B-430
flumioxazin + glyphosate
cloquintocet


B-431
imazapic + glyphosate
cloquintocet


B-432
imazethapyr + glyphosate
cloquintocet


B-433
isoxaflutol + H-1
cloquintocet


B-434
isoxaflutol + glyphosate
cloquintocet


B-435
metazachlor + H-1
cloquintocet


B-436
metazachlor + glyphosate
cloquintocet


B-437
metazachlor + mesotrione
cloquintocet


B-438
metazachlor + nicosulfuron
cloquintocet


B-439
metazachlor + terbuthylazine
cloquintocet


B-440
metazachlor + topramezone
cloquintocet


B-441
metribuzin + glyphosate
cloquintocet


B-442
pendimethalin + H-1
cloquintocet


B-443
pendimethalin + clodinafop-propargyl
cloquintocet


B-444
pendimethalin + fenoxaprop-P-ethyl
cloquintocet


B-445
pendimethalin + flupyrsulfuron-methyl-sodium
cloquintocet


B-446
pendimethalin + glyphosate
cloquintocet


B-447
pendimethalin + mesosulfuron-methyl
cloquintocet


B-448
pendimethalin + mesotrione
cloquintocet


B-449
pendimethalin + nicosulfuron
cloquintocet


B-450
pendimethalin + pinoxaden
cloquintocet


B-451
pendimethalin + pyroxsulam
cloquintocet


B-452
pendimethalin + tembotrione
cloquintocet


B-453
pendimethalin + topramezone
cloquintocet


B-454
pyroxasulfone + tembotrione
cloquintocet


B-455
pyroxasulfone + topramezone
cloquintocet


B-456
sulfentrazone + glyphosate
cloquintocet


B-457
terbuthylazine + H-1
cloquintocet


B-458
terbuthylazine + foramsulfuron
cloquintocet


B-459
terbuthylazine + glyphosate
cloquintocet


B-460
terbuthylazine + mesotrione
cloquintocet


B-461
terbuthylazine + nicosulfuron
cloquintocet


B-462
terbuthylazine + tembotrione
cloquintocet


B-463
terbuthylazine + topramezone
cloquintocet


B-464
trifluralin + glyphosate
cloquintocet


B-465
clodinafop-propargyl
dichlormid


B-466
cycloxydim
dichlormid


B-467
cyhalofop-butyl
dichlormid


B-468
fenoxaprop-P-ethyl
dichlormid


B-469
pinoxaden
dichlormid


B-470
profoxydim
dichlormid


B-471
tepraloxydim
dichlormid


B-472
tralkoxydim
dichlormid


B-473
esprocarb
dichlormid


B-474
prosulfocarb
dichlormid


B-475
thiobencarb
dichlormid


B-476
triallate
dichlormid


B-477
bensulfuron-methyl
dichlormid


B-478
bispyribac-sodium
dichlormid


B-479
cyclosulfamuron
dichlormid


B-480
flumetsulam
dichlormid


B-481
flupyrsulfuron-methyl-sodium
dichlormid


B-482
foramsulfuron
dichlormid


B-483
imazamox
dichlormid


B-484
imazapic
dichlormid


B-485
imazapyr
dichlormid


B-486
imazaquin
dichlormid


B-487
imazethapyr
dichlormid


B-488
imazosulfuron
dichlormid


B-489
iodosulfuron-methyl-sodium
dichlormid


B-490
mesosulfuron
dichlormid


B-491
nicosulfuron
dichlormid


B-492
penoxsulam
dichlormid


B-493
propoxycarbazone-sodium
dichlormid


B-494
pyrazosulfuron-ethyl
dichlormid


B-495
pyroxsulam
dichlormid


B-496
rimsulfuron
dichlormid


B-497
sulfosulfuron
dichlormid


B-498
thiencarbazone-methyl
dichlormid


B-499
tritosulfuron
dichlormid


B-500
2,4-D and its salts and esters
dichlormid


B-501
aminopyralid and its salts and esters
dichlormid


B-502
clopyralid and its salts and esters
dichlormid


B-503
dicamba and its salts and esters
dichlormid


B-504
fluroxypyr-meptyl
dichlormid


B-505
quinclorac
dichlormid


B-506
quinmerac
dichlormid


B-507
H-9
dichlormid


B-508
diflufenzopyr
dichlormid


B-509
diflufenzopyr-sodium
dichlormid


B-510
clomazone
dichlormid


B-511
diflufenican
dichlormid


B-512
fluorochloridone
dichlormid


B-513
isoxaflutol
dichlormid


B-514
mesotrione
dichlormid


B-515
picolinafen
dichlormid


B-516
sulcotrione
dichlormid


B-517
tefuryltrione
dichlormid


B-518
tembotrione
dichlormid


B-519
topramezone
dichlormid


B-520
H-7
dichlormid


B-521
atrazine
dichlormid


B-522
diuron
dichlormid


B-523
fluometuron
dichlormid


B-524
hexazinone
dichlormid


B-525
isoproturon
dichlormid


B-526
metribuzin
dichlormid


B-527
propanil
dichlormid


B-528
terbuthylazine
dichlormid


B-529
paraquat dichloride
dichlormid


B-530
flumioxazin
dichlormid


B-531
oxyfluorfen
dichlormid


B-532
saflufenacil
dichlormid


B-533
sulfentrazone
dichlormid


B-534
H-1
dichlormid


B-535
H-2
dichlormid


B-536
glyphosate
dichlormid


B-537
glyphosate-isopropylammonium
dichlormid


B-538
glyphosate-trimesium (sulfosate)
dichlormid


B-539
glufosinate
dichlormid


B-540
glufosinate-ammonium
dichlormid


B-541
pendimethalin
dichlormid


B-542
trifluralin
dichlormid


B-543
acetochlor
dichlormid


B-544
cafenstrole
dichlormid


B-545
dimethenamid-P
dichlormid


B-546
fentrazamide
dichlormid


B-547
flufenacet
dichlormid


B-548
mefenacet
dichlormid


B-549
metazachlor
dichlormid


B-550
metolachlor-S
dichlormid


B-551
pyroxasulfone
dichlormid


B-552
isoxaben
dichlormid


B-553
dymron
dichlormid


B-554
indanofan
dichlormid


B-555
oxaziclomefone
dichlormid


B-556
triaziflam
dichlormid


B-557
atrazine + H-1
dichlormid


B-558
atrazine + glyphosate
dichlormid


B-559
atrazine + mesotrione
dichlormid


B-560
atrazine + nicosulfuron
dichlormid


B-561
atrazine + tembotrione
dichlormid


B-562
atrazine + topramezone
dichlormid


B-563
clomazone + glyphosate
dichlormid


B-564
diflufenican + clodinafop-propargyl
dichlormid


B-565
diflufenican + fenoxaprop-p-ethyl
dichlormid


B-566
diflufenican + flupyrsulfuron-methyl-sodium
dichlormid


B-567
diflufenican + glyphosate
dichlormid


B-568
diflufenican + mesosulfuron-methyl
dichlormid


B-569
diflufenican + pinoxaden
dichlormid


B-570
diflufenican + pyroxsulam
dichlormid


B-571
flumetsulam + glyphosate
dichlormid


B-572
flumioxazin + glyphosate
dichlormid


B-573
imazapic + glyphosate
dichlormid


B-574
imazethapyr + glyphosate
dichlormid


B-575
isoxaflutol + H-1
dichlormid


B-576
isoxaflutol + glyphosate
dichlormid


B-577
metazachlor + H-1
dichlormid


B-578
metazachlor + glyphosate
dichlormid


B-579
metazachlor + mesotrione
dichlormid


B-580
metazachlor + nicosulfuron
dichlormid


B-581
metazachlor + terbuthylazine
dichlormid


B-582
metazachlor + topramezone
dichlormid


B-583
metribuzin + glyphosate
dichlormid


B-584
pendimethalin + H-1
dichlormid


B-585
pendimethalin + clodinafop-propargyl
dichlormid


B-586
pendimethalin + fenoxaprop-P-ethyl
dichlormid


B-587
pendimethalin + flupyrsulfuron-methyl-sodium
dichlormid


B-588
pendimethalin + glyphosate
dichlormid


B-589
pendimethalin + mesosulfuron-methyl
dichlormid


B-590
pendimethalin + mesotrione
dichlormid


B-591
pendimethalin + nicosulfuron
dichlormid


B-592
pendimethalin + pinoxaden
dichlormid


B-593
pendimethalin + pyroxsulam
dichlormid


B-594
pendimethalin + tembotrione
dichlormid


B-595
pendimethalin + topramezone
dichlormid


B-596
pyroxasulfone + tembotrione
dichlormid


B-597
pyroxasulfone + topramezone
dichlormid


B-598
sulfentrazone + glyphosate
dichlormid


B-599
terbuthylazine + H-1
dichlormid


B-600
terbuthylazine + foramsulfuron
dichlormid


B-601
terbuthylazine + glyphosate
dichlormid


B-602
terbuthylazine + mesotrione
dichlormid


B-603
terbuthylazine + nicosulfuron
dichlormid


B-604
terbuthylazine + tembotrione
dichlormid


B-605
terbuthylazine + topramezone
dichlormid


B-606
trifluralin + glyphosate
dichlormid


B-607
clodinafop-propargyl
fenchlorazole


B-608
cycloxydim
fenchlorazole


B-609
cyhalofop-butyl
fenchlorazole


B-610
fenoxaprop-P-ethyl
fenchlorazole


B-611
pinoxaden
fenchlorazole


B-612
profoxydim
fenchlorazole


B-613
tepraloxydim
fenchlorazole


B-614
tralkoxydim
fenchlorazole


B-615
esprocarb
fenchlorazole


B-616
prosulfocarb
fenchlorazole


B-617
thiobencarb
fenchlorazole


B-618
triallate
fenchlorazole


B-619
bensulfuron-methyl
fenchlorazole


B-620
bispyribac-sodium
fenchlorazole


B-621
cyclosulfamuron
fenchlorazole


B-622
flumetsulam
fenchlorazole


B-623
flupyrsulfuron-methyl-sodium
fenchlorazole


B-624
foramsulfuron
fenchlorazole


B-625
imazamox
fenchlorazole


B-626
imazapic
fenchlorazole


B-627
imazapyr
fenchlorazole


B-628
imazaquin
fenchlorazole


B-629
imazethapyr
fenchlorazole


B-630
imazosulfuron
fenchlorazole


B-631
iodosulfuron-methyl-sodium
fenchlorazole


B-632
mesosulfuron
fenchlorazole


B-633
nicosulfuron
fenchlorazole


B-634
penoxsulam
fenchlorazole


B-635
propoxycarbazone-sodium
fenchlorazole


B-636
pyrazosulfuron-ethyl
fenchlorazole


B-637
pyroxsulam
fenchlorazole


B-638
rimsulfuron
fenchlorazole


B-639
sulfosulfuron
fenchlorazole


B-640
thiencarbazone-methyl
fenchlorazole


B-641
tritosulfuron
fenchlorazole


B-642
2,4-D and its salts and esters
fenchlorazole


B-643
aminopyralid and its salts and esters
fenchlorazole


B-644
clopyralid and its salts and esters
fenchlorazole


B-645
dicamba and its salts and esters
fenchlorazole


B-646
fluroxypyr-meptyl
fenchlorazole


B-647
quinclorac
fenchlorazole


B-648
quinmerac
fenchlorazole


B-649
H-9
fenchlorazole


B-650
diflufenzopyr
fenchlorazole


B-651
diflufenzopyr-sodium
fenchlorazole


B-652
clomazone
fenchlorazole


B-653
diflufenican
fenchlorazole


B-654
fluorochloridone
fenchlorazole


B-655
isoxaflutol
fenchlorazole


B-656
mesotrione
fenchlorazole


B-657
picolinafen
fenchlorazole


B-658
sulcotrione
fenchlorazole


B-659
tefuryltrione
fenchlorazole


B-660
tembotrione
fenchlorazole


B-661
topramezone
fenchlorazole


B-662
H-7
fenchlorazole


B-663
atrazine
fenchlorazole


B-664
diuron
fenchlorazole


B-665
fluometuron
fenchlorazole


B-666
hexazinone
fenchlorazole


B-667
isoproturon
fenchlorazole


B-668
metribuzin
fenchlorazole


B-669
propanil
fenchlorazole


B-670
terbuthylazine
fenchlorazole


B-671
paraquat dichloride
fenchlorazole


B-672
flumioxazin
fenchlorazole


B-673
oxyfluorfen
fenchlorazole


B-674
saflufenacil
fenchlorazole


B-675
sulfentrazone
fenchlorazole


B-676
H-1
fenchlorazole


B-677
H-2
fenchlorazole


B-678
glyphosate
fenchlorazole


B-679
glyphosate-isopropylammonium
fenchlorazole


B-680
glyphosate-trimesium (sulfosate)
fenchlorazole


B-681
glufosinate
fenchlorazole


B-682
glufosinate-ammonium
fenchlorazole


B-683
pendimethalin
fenchlorazole


B-684
trifluralin
fenchlorazole


B-685
acetochlor
fenchlorazole


B-686
cafenstrole
fenchlorazole


B-687
dimethenamid-P
fenchlorazole


B-688
fentrazamide
fenchlorazole


B-689
flufenacet
fenchlorazole


B-690
mefenacet
fenchlorazole


B-691
metazachlor
fenchlorazole


B-692
metolachlor-S
fenchlorazole


B-693
pyroxasulfone
fenchlorazole


B-694
isoxaben
fenchlorazole


B-695
dymron
fenchlorazole


B-696
indanofan
fenchlorazole


B-697
oxaziclomefone
fenchlorazole


B-698
triaziflam
fenchlorazole


B-699
atrazine + H-1
fenchlorazole


B-700
atrazine + glyphosate
fenchlorazole


B-701
atrazine + mesotrione
fenchlorazole


B-702
atrazine + nicosulfuron
fenchlorazole


B-703
atrazine + tembotrione
fenchlorazole


B-704
atrazine + topramezone
fenchlorazole


B-705
clomazone + glyphosate
fenchlorazole


B-706
diflufenican + clodinafop-propargyl
fenchlorazole


B-707
diflufenican + fenoxaprop-P-ethyl
fenchlorazole


B-708
diflufenican + flupyrsulfuron-methyl-sodium
fenchlorazole


B-709
diflufenican + glyphosate
fenchlorazole


B-710
diflufenican + mesosulfuron-methyl
fenchlorazole


B-711
diflufenican + pinoxaden
fenchlorazole


B-712
diflufenican + pyroxsulam
fenchlorazole


B-713
flumetsulam + glyphosate
fenchlorazole


B-714
flumioxazin + glyphosate
fenchlorazole


B-715
imazapic + glyphosate
fenchlorazole


B-716
imazethapyr + glyphosate
fenchlorazole


B-717
isoxaflutol + H-1
fenchlorazole


B-718
isoxaflutol + glyphosate
fenchlorazole


B-719
metazachlor + H-1
fenchlorazole


B-720
metazachlor + glyphosate
fenchlorazole


B-721
metazachlor + mesotrione
fenchlorazole


B-722
metazachlor + nicosulfuron
fenchlorazole


B-723
metazachlor + terbuthylazine
fenchlorazole


B-724
metazachlor + topramezone
fenchlorazole


B-725
metribuzin + glyphosate
fenchlorazole


B-726
pendimethalin + H-1
fenchlorazole


B-727
pendimethalin + clodinafop-propargyl
fenchlorazole


B-728
pendimethalin + fenoxaprop-P-ethyl
fenchlorazole


B-729
pendimethalin + flupyrsulfuron-methyl-sodium
fenchlorazole


B-730
pendimethalin + glyphosate
fenchlorazole


B-731
pendimethalin + mesosulfuron-methyl
fenchlorazole


B-732
pendimethalin + mesotrione
fenchlorazole


B-733
pendimethalin + nicosulfuron
fenchlorazole


B-734
pendimethalin + pinoxaden
fenchlorazole


B-735
pendimethalin + pyroxsulam
fenchlorazole


B-736
pendimethalin + tembotrione
fenchlorazole


B-737
pendimethalin + topramezone
fenchlorazole


B-738
pyroxasulfone + tembotrione
fenchlorazole


B-739
pyroxasulfone + topramezone
fenchlorazole


B-740
sulfentrazone + glyphosate
fenchlorazole


B-741
terbuthylazine + H-1
fenchlorazole


B-742
terbuthylazine + foramsulfuron
fenchlorazole


B-743
terbuthylazine + glyphosate
fenchlorazole


B-744
terbuthylazine + mesotrione
fenchlorazole


B-745
terbuthylazine + nicosulfuron
fenchlorazole


B-746
terbuthylazine + tembotrione
fenchlorazole


B-747
terbuthylazine + topramezone
fenchlorazole


B-748
trifluralin + glyphosate
fenchlorazole


B-749
clodinafop-propargyl
fenclorim


B-750
cycloxydim
fenclorim


B-751
cyhalofop-butyl
fenclorim


B-752
fenoxaprop-P-ethyl
fenclorim


B-753
pinoxaden
fenclorim


B-754
profoxydim
fenclorim


B-755
tepraloxydim
fenclorim


B-756
tralkoxydim
fenclorim


B-757
esprocarb
fenclorim


B-758
prosulfocarb
fenclorim


B-759
thiobencarb
fenclorim


B-760
triallate
fenclorim


B-761
bensulfuron-methyl
fenclorim


B-762
bispyribac-sodium
fenclorim


B-763
cyclosulfamuron
fenclorim


B-764
flumetsulam
fenclorim


B-765
flupyrsulfuron-methyl-sodium
fenclorim


B-766
foramsulfuron
fenclorim


B-767
imazamox
fenclorim


B-768
imazapic
fenclorim


B-769
imazapyr
fenclorim


B-770
imazaquin
fenclorim


B-771
imazethapyr
fenclorim


B-772
imazosulfuron
fenclorim


B-773
iodosulfuron-methyl-sodium
fenclorim


B-774
mesosulfuron
fenclorim


B-775
nicosulfuron
fenclorim


B-776
penoxsulam
fenclorim


B-777
propoxycarbazone-sodium
fenclorim


B-778
pyrazosulfuron-ethyl
fenclorim


B-779
pyroxsulam
fenclorim


B-780
rimsulfuron
fenclorim


B-781
sulfosulfuron
fenclorim


B-782
thiencarbazone-methyl
fenclorim


B-783
tritosulfuron
fenclorim


B-784
2,4-D and its salts and esters
fenclorim


B-785
aminopyralid and its salts and esters
fenclorim


B-786
clopyralid and its salts and esters
fenclorim


B-787
dicamba and its salts and esters
fenclorim


B-788
fluroxypyr-meptyl
fenclorim


B-789
quinclorac
fenclorim


B-790
quinmerac
fenclorim


B-791
H-9
fenclorim


B-792
diflufenzopyr
fenclorim


B-793
diflufenzopyr-sodium
fenclorim


B-794
clomazone
fenclorim


B-795
diflufenican
fenclorim


B-796
fluorochloridone
fenclorim


B-797
isoxaflutol
fenclorim


B-798
mesotrione
fenclorim


B-799
picolinafen
fenclorim


B-800
sulcotrione
fenclorim


B-801
tefuryltrione
fenclorim


B-802
tembotrione
fenclorim


B-803
topramezone
fenclorim


B-804
H-7
fenclorim


B-805
atrazine
fenclorim


B-806
diuron
fenclorim


B-807
fluometuron
fenclorim


B-808
hexazinone
fenclorim


B-809
isoproturon
fenclorim


B-810
metribuzin
fenclorim


B-811
propanil
fenclorim


B-812
terbuthylazine
fenclorim


B-813
paraquat dichloride
fenclorim


B-814
flumioxazin
fenclorim


B-815
oxyfluorfen
fenclorim


B-816
saflufenacil
fenclorim


B-817
sulfentrazone
fenclorim


B-818
H-1
fenclorim


B-819
H-2
fenclorim


B-820
glyphosate
fenclorim


B-821
glyphosate-isopropylammonium
fenclorim


B-822
glyphosate-trimesium (sulfosate)
fenclorim


B-823
glufosinate
fenclorim


B-824
glufosinate-ammonium
fenclorim


B-825
pendimethalin
fenclorim


B-826
trifluralin
fenclorim


B-827
acetochlor
fenclorim


B-828
cafenstrole
fenclorim


B-829
dimethenamid-P
fenclorim


B-830
fentrazamide
fenclorim


B-831
flufenacet
fenclorim


B-832
mefenacet
fenclorim


B-833
metazachlor
fenclorim


B-834
metolachlor-S
fenclorim


B-835
pyroxasulfone
fenclorim


B-836
isoxaben
fenclorim


B-837
dymron
fenclorim


B-838
indanofan
fenclorim


B-839
oxaziclomefone
fenclorim


B-840
triaziflam
fenclorim


B-841
atrazine + H-1
fenclorim


B-842
atrazine + glyphosate
fenclorim


B-843
atrazine + mesotrione
fenclorim


B-844
atrazine + nicosulfuron
fenclorim


B-845
atrazine + tembotrione
fenclorim


B-846
atrazine + topramezone
fenclorim


B-847
clomazone + glyphosate
fenclorim


B-848
diflufenican + clodinafop-propargyl
fenclorim


B-849
diflufenican + fenoxaprop-P-ethyl
fenclorim


B-850
diflufenican + flupyrsulfuron-methyl-sodium
fenclorim


B-851
diflufenican + glyphosate
fenclorim


B-852
diflufenican + mesosulfuron-methyl
fenclorim


B-853
diflufenican + pinoxaden
fenclorim


B-854
diflufenican + pyroxsulam
fenclorim


B-855
flumetsulam + glyphosate
fenclorim


B-856
flumioxazin + glyphosate
fenclorim


B-857
imazapic + glyphosate
fenclorim


B-858
imazethapyr + glyphosate
fenclorim


B-859
isoxaflutol + H-1
fenclorim


B-860
isoxaflutol + glyphosate
fenclorim


B-861
metazachlor + H-1
fenclorim


B-862
metazachlor + glyphosate
fenclorim


B-863
metazachlor + mesotrione
fenclorim


B-864
metazachlor + nicosulfuron
fenclorim


B-865
metazachlor + terbuthylazine
fenclorim


B-866
metazachlor + topramezone
fenclorim


B-867
metribuzin + glyphosate
fenclorim


B-868
pendimethalin + H-1
fenclorim


B-869
pendimethalin + clodinafop-propargyl
fenclorim


B-870
pendimethalin + fenoxaprop-P-ethyl
fenclorim


B-871
pendimethalin + flupyrsulfuron-methyl-sodium
fenclorim


B-872
pendimethalin + glyphosate
fenclorim


B-873
pendimethalin + mesosulfuron-methyl
fenclorim


B-874
pendimethalin + mesotrione
fenclorim


B-875
pendimethalin + nicosulfuron
fenclorim


B-876
pendimethalin + pinoxaden
fenclorim


B-877
pendimethalin + pyroxsulam
fenclorim


B-878
pendimethalin + tembotrione
fenclorim


B-879
pendimethalin + topramezone
fenclorim


B-880
pyroxasulfone + tembotrione
fenclorim


B-881
pyroxasulfone + topramezone
fenclorim


B-882
sulfentrazone + glyphosate
fenclorim


B-883
terbuthylazine + H-1
fenclorim


B-884
terbuthylazine + foramsulfuron
fenclorim


B-885
terbuthylazine + glyphosate
fenclorim


B-886
terbuthylazine + mesotrione
fenclorim


B-887
terbuthylazine + nicosulfuron
fenclorim


B-888
terbuthylazine + tembotrione
fenclorim


B-889
terbuthylazine + topramezone
fenclorim


B-890
trifluralin + glyphosate
fenclorim


B-891
clodinafop-propargyl
isoxadifen


B-892
cycloxydim
isoxadifen


B-893
cyhalofop-butyl
isoxadifen


B-894
fenoxaprop-P-ethyl
isoxadifen


B-895
pinoxaden
isoxadifen


B-896
profoxydim
isoxadifen


B-897
tepraloxydim
isoxadifen


B-898
tralkoxydim
isoxadifen


B-899
esprocarb
isoxadifen


B-900
prosulfocarb
isoxadifen


B-901
thiobencarb
isoxadifen


B-902
triallate
isoxadifen


B-903
bensulfuron-methyl
isoxadifen


B-904
bispyribac-sodium
isoxadifen


B-905
cyclosulfamuron
isoxadifen


B-906
flumetsulam
isoxadifen


B-907
flupyrsulfuron-methyl-sodium
isoxadifen


B-908
foramsulfuron
isoxadifen


B-909
imazamox
isoxadifen


B-910
imazapic
isoxadifen


B-911
imazapyr
isoxadifen


B-912
imazaquin
isoxadifen


B-913
imazethapyr
isoxadifen


B-914
imazosulfuron
isoxadifen


B-915
iodosulfuron-methyl-sodium
isoxadifen


B-916
mesosulfuron
isoxadifen


B-917
nicosulfuron
isoxadifen


B-918
penoxsulam
isoxadifen


B-919
propoxycarbazone-sodium
isoxadifen


B-920
pyrazosulfuron-ethyl
isoxadifen


B-921
pyroxsulam
isoxadifen


B-922
rimsulfuron
isoxadifen


B-923
sulfosulfuron
isoxadifen


B-924
thiencarbazone-methyl
isoxadifen


B-925
tritosulfuron
isoxadifen


B-926
2,4-D and its salts and esters
isoxadifen


B-927
aminopyralid and its salts and esters
isoxadifen


B-928
clopyralid and its salts and esters
isoxadifen


B-929
dicamba and its salts and esters
isoxadifen


B-930
fluroxypyr-meptyl
isoxadifen


B-931
quinclorac
isoxadifen


B-932
quinmerac
isoxadifen


B-933
H-9
isoxadifen


B-934
diflufenzopyr
isoxadifen


B-935
diflufenzopyr-sodium
isoxadifen


B-936
clomazone
isoxadifen


B-937
diflufenican
isoxadifen


B-938
fluorochloridone
isoxadifen


B-939
isoxaflutol
isoxadifen


B-940
mesotrione
isoxadifen


B-941
picolinafen
isoxadifen


B-942
sulcotrione
isoxadifen


B-943
tefuryltrione
isoxadifen


B-944
tembotrione
isoxadifen


B-945
topramezone
isoxadifen


B-946
H-7
isoxadifen


B-947
atrazine
isoxadifen


B-948
diuron
isoxadifen


B-949
fluometuron
isoxadifen


B-950
hexazinone
isoxadifen


B-951
isoproturon
isoxadifen


B-952
metribuzin
isoxadifen


B-953
propanil
isoxadifen


B-954
terbuthylazine
isoxadifen


B-955
paraquat dichloride
isoxadifen


B-956
flumioxazin
isoxadifen


B-957
oxyfluorfen
isoxadifen


B-958
saflufenacil
isoxadifen


B-959
sulfentrazone
isoxadifen


B-960
H-1
isoxadifen


B-961
H-2
isoxadifen


B-962
glyphosate
isoxadifen


B-963
glyphosate-isopropylammonium
isoxadifen


B-964
glyphosate-trimesium (sulfosate)
isoxadifen


B-965
glufosinate
isoxadifen


B-966
glufosinate-ammonium
isoxadifen


B-967
pendimethalin
isoxadifen


B-968
trifluralin
isoxadifen


B-969
acetochlor
isoxadifen


B-970
cafenstrole
isoxadifen


B-971
dimethenamid-P
isoxadifen


B-972
fentrazamide
isoxadifen


B-973
flufenacet
isoxadifen


B-974
mefenacet
isoxadifen


B-975
metazachlor
isoxadifen


B-976
metolachlor-S
isoxadifen


B-977
pyroxasulfone
isoxadifen


B-978
isoxaben
isoxadifen


B-979
dymron
isoxadifen


B-980
indanofan
isoxadifen


B-981
oxaziclomefone
isoxadifen


B-982
triaziflam
isoxadifen


B-983
atrazine + H-1
isoxadifen


B-984
atrazine + glyphosate
isoxadifen


B-985
atrazine + mesotrione
isoxadifen


B-986
atrazine + nicosulfuron
isoxadifen


B-987
atrazine + tembotrione
isoxadifen


B-988
atrazine + topramezone
isoxadifen


B-989
clomazone + glyphosate
isoxadifen


B-990
diflufenican + clodinafop-propargyl
isoxadifen


B-991
diflufenican + fenoxaprop-P-ethyl
isoxadifen


B-992
diflufenican + flupyrsulfuron-methyl-sodium
isoxadifen


B-993
diflufenican + glyphosate
isoxadifen


B-994
diflufenican + mesosulfuron-methyl
isoxadifen


B-995
diflufenican + pinoxaden
isoxadifen


B-996
diflufenican + pyroxsulam
isoxadifen


B-997
flumetsulam + glyphosate
isoxadifen


B-998
flumioxazin + glyphosate
isoxadifen


B-999
imazapic + glyphosate
isoxadifen


B-1000
imazethapyr + glyphosate
isoxadifen


B-1001
isoxaflutol + H-1
isoxadifen


B-1002
isoxaflutol + glyphosate
isoxadifen


B-1003
metazachlor + H-1
isoxadifen


B-1004
metazachlor + glyphosate
isoxadifen


B-1005
metazachlor + mesotrione
isoxadifen


B-1006
metazachlor + nicosulfuron
isoxadifen


B-1007
metazachlor + terbuthylazine
isoxadifen


B-1008
metazachlor + topramezone
isoxadifen


B-1009
metribuzin + glyphosate
isoxadifen


B-1010
pendimethalin + H-1
isoxadifen


B-1011
pendimethalin + clodinafop-propargyl
isoxadifen


B-1012
pendimethalin + fenoxaprop-P-ethyl
isoxadifen


B-1013
pendimethalin + flupyrsulfuron-methyl-sodium
isoxadifen


B-1014
pendimethalin + glyphosate
isoxadifen


B-1015
pendimethalin + mesosulfuron-methyl
isoxadifen


B-1016
pendimethalin + mesotrione
isoxadifen


B-1017
pendimethalin + nicosulfuron
isoxadifen


B-1018
pendimethalin + pinoxaden
isoxadifen


B-1019
pendimethalin + pyroxsulam
isoxadifen


B-1020
pendimethalin + tembotrione
isoxadifen


B-1021
pendimethalin + topramezone
isoxadifen


B-1022
pyroxasulfone + tembotrione
isoxadifen


B-1023
pyroxasulfone + topramezone
isoxadifen


B-1024
sulfentrazone + glyphosate
isoxadifen


B-1025
terbuthylazine + H-1
isoxadifen


B-1026
terbuthylazine + foramsulfuron
isoxadifen


B-1027
terbuthylazine + glyphosate
isoxadifen


B-1028
terbuthylazine + mesotrione
isoxadifen


B-1029
terbuthylazine + nicosulfuron
isoxadifen


B-1030
terbuthylazine + tembotrione
isoxadifen


B-1031
terbuthylazine + topramezone
isoxadifen


B-1032
trifluralin + glyphosate
isoxadifen


B-1033
clodinafop-propargyl
mefenpyr


B-1034
cycloxydim
mefenpyr


B-1035
cyhalofop-butyl
mefenpyr


B-1036
fenoxaprop-P-ethyl
mefenpyr


B-1037
pinoxaden
mefenpyr


B-1038
profoxydim
mefenpyr


B-1039
tepraloxydim
mefenpyr


B-1040
tralkoxydim
mefenpyr


B-1041
esprocarb
mefenpyr


B-1042
prosulfocarb
mefenpyr


B-1043
thiobencarb
mefenpyr


B-1044
triallate
mefenpyr


B-1045
bensulfuron-methyl
mefenpyr


B-1046
bispyribac-sodium
mefenpyr


B-1047
cyclosulfamuron
mefenpyr


B-1048
flumetsulam
mefenpyr


B-1049
flupyrsulfuron-methyl-sodium
mefenpyr


B-1050
foramsulfuron
mefenpyr


B-1051
imazamox
mefenpyr


B-1052
imazapic
mefenpyr


B-1053
imazapyr
mefenpyr


B-1054
imazaquin
mefenpyr


B-1055
imazethapyr
mefenpyr


B-1056
imazosulfuron
mefenpyr


B-1057
iodosulfuron-methyl-sodium
mefenpyr


B-1058
mesosulfuron
mefenpyr


B-1059
nicosulfuron
mefenpyr


B-1060
penoxsulam
mefenpyr


B-1061
propoxycarbazone-sodium
mefenpyr


B-1062
pyrazosulfuron-ethyl
mefenpyr


B-1063
pyroxsulam
mefenpyr


B-1064
rimsulfuron
mefenpyr


B-1065
sulfosulfuron
mefenpyr


B-1066
thiencarbazone-methyl
mefenpyr


B-1067
tritosulfuron
mefenpyr


B-1068
2,4-D and its salts and esters
mefenpyr


B-1069
aminopyralid and its salts and esters
mefenpyr


B-1070
clopyralid and its salts and esters
mefenpyr


B-1071
dicamba and its salts and esters
mefenpyr


B-1072
fluroxypyr-meptyl
mefenpyr


B-1073
quinclorac
mefenpyr


B-1074
quinmerac
mefenpyr


B-1075
H-9
mefenpyr


B-1076
diflufenzopyr
mefenpyr


B-1077
diflufenzopyr-sodium
mefenpyr


B-1078
clomazone
mefenpyr


B-1079
diflufenican
mefenpyr


B-1080
fluorochloridone
mefenpyr


B-1081
isoxaflutol
mefenpyr


B-1082
mesotrione
mefenpyr


B-1083
picolinafen
mefenpyr


B-1084
sulcotrione
mefenpyr


B-1085
tefuryltrione
mefenpyr


B-1086
tembotrione
mefenpyr


B-1087
topramezone
mefenpyr


B-1088
H-7
mefenpyr


B-1089
atrazine
mefenpyr


B-1090
diuron
mefenpyr


B-1091
fluometuron
mefenpyr


B-1092
hexazinone
mefenpyr


B-1093
isoproturon
mefenpyr


B-1094
metribuzin
mefenpyr


B-1095
propanil
mefenpyr


B-1096
terbuthylazine
mefenpyr


B-1097
paraquat dichloride
mefenpyr


B-1098
flumioxazin
mefenpyr


B-1099
oxyfluorfen
mefenpyr


B-1100
saflufenacil
mefenpyr


B-1101
sulfentrazone
mefenpyr


B-1102
H-1
mefenpyr


B-1103
H-2
mefenpyr


B-1104
glyphosate
mefenpyr


B-1105
glyphosate-isopropylammonium
mefenpyr


B-1106
glyphosate-trimesium (sulfosate)
mefenpyr


B-1107
glufosinate
mefenpyr


B-1108
glufosinate-ammonium
mefenpyr


B-1109
pendimethalin
mefenpyr


B-1110
trifluralin
mefenpyr


B-1111
acetochlor
mefenpyr


B-1112
cafenstrole
mefenpyr


B-1113
dimethenamid-P
mefenpyr


B-1114
fentrazamide
mefenpyr


B-1115
flufenacet
mefenpyr


B-1116
mefenacet
mefenpyr


B-1117
metazachlor
mefenpyr


B-1118
metolachlor-S
mefenpyr


B-1119
pyroxasulfone
mefenpyr


B-1120
isoxaben
mefenpyr


B-1121
dymron
mefenpyr


B-1122
indanofan
mefenpyr


B-1123
oxaziclomefone
mefenpyr


B-1124
triaziflam
mefenpyr


B-1125
atrazine + H-1
mefenpyr


B-1126
atrazine + glyphosate
mefenpyr


B-1127
atrazine + mesotrione
mefenpyr


B-1128
atrazine + nicosulfuron
mefenpyr


B-1129
atrazine + tembotrione
mefenpyr


B-1130
atrazine + topramezone
mefenpyr


B-1131
clomazone + glyphosate
mefenpyr


B-1132
diflufenican + clodinafop-propargyl
mefenpyr


B-1133
diflufenican + fenoxaprop-P-ethyl
mefenpyr


B-1134
diflufenican + flupyrsulfuron-methyl-sodium
mefenpyr


B-1135
diflufenican + glyphosate
mefenpyr


B-1136
diflufenican + mesosulfuron-methyl
mefenpyr


B-1137
diflufenican + pinoxaden
mefenpyr


B-1138
diflufenican + pyroxsulam
mefenpyr


B-1139
flumetsulam + glyphosate
mefenpyr


B-1140
flumioxazin + glyphosate
mefenpyr


B-1141
imazapic + glyphosate
mefenpyr


B-1142
imazethapyr + glyphosate
mefenpyr


B-1143
isoxaflutol + H-1
mefenpyr


B-1144
isoxaflutol + glyphosate
mefenpyr


B-1145
metazachlor + H-1
mefenpyr


B-1146
metazachlor + glyphosate
mefenpyr


B-1147
metazachlor + mesotrione
mefenpyr


B-1148
metazachlor + nicosulfuron
mefenpyr


B-1149
metazachlor + terbuthylazine
mefenpyr


B-1150
metazachlor + topramezone
mefenpyr


B-1151
metribuzin + glyphosate
mefenpyr


B-1152
pendimethalin + H-1
mefenpyr


B-1153
pendimethalin + clodinafop-propargyl
mefenpyr


B-1154
pendimethalin + fenoxaprop-P-ethyl
mefenpyr


B-1155
pendimethalin + flupyrsulfuron-methyl-sodium
mefenpyr


B-1156
pendimethalin + glyphosate
mefenpyr


B-1157
pendimethalin + mesosulfuron-methyl
mefenpyr


B-1158
pendimethalin + mesotrione
mefenpyr


B-1159
pendimethalin + nicosulfuron
mefenpyr


B-1160
pendimethalin + pinoxaden
mefenpyr


B-1161
pendimethalin + pyroxsulam
mefenpyr


B-1162
pendimethalin + tembotrione
mefenpyr


B-1163
pendimethalin + topramezone
mefenpyr


B-1164
pyroxasulfone + tembotrione
mefenpyr


B-1165
pyroxasulfone + topramezone
mefenpyr


B-1166
sulfentrazone + glyphosate
mefenpyr


B-1167
terbuthylazine + H-1
mefenpyr


B-1168
terbuthylazine + foramsulfuron
mefenpyr


B-1169
terbuthylazine + glyphosate
mefenpyr


B-1170
terbuthylazine + mesotrione
mefenpyr


B-1171
terbuthylazine + nicosulfuron
mefenpyr


B-1172
terbuthylazine + tembotrione
mefenpyr


B-1173
terbuthylazine + topramezone
mefenpyr


B-1174
trifluralin + glyphosate
mefenpyr


B-1175
clodinafop-propargyl
H-12


B-1176
cycloxydim
H-12


B-1177
cyhalofop-butyl
H-12


B-1178
fenoxaprop-P-ethyl
H-12


B-1179
pinoxaden
H-12


B-1180
profoxydim
H-12


B-1181
tepraloxydim
H-12


B-1182
tralkoxydim
H-12


B-1183
esprocarb
H-12


B-1184
prosulfocarb
H-12


B-1185
thiobencarb
H-12


B-1186
triallate
H-12


B-1187
bensulfuron-methyl
H-12


B-1188
bispyribac-sodium
H-12


B-1189
cyclosulfamuron
H-12


B-1190
flumetsulam
H-12


B-1191
flupyrsulfuron-methyl-sodium
H-12


B-1192
foramsulfuron
H-12


B-1193
imazamox
H-12


B-1194
imazapic
H-12


B-1195
imazapyr
H-12


B-1196
imazaquin
H-12


B-1197
imazethapyr
H-12


B-1198
imazosulfuron
H-12


B-1199
iodosulfuron-methyl-sodium
H-12


B-1200
mesosulfuron
H-12


B-1201
nicosulfuron
H-12


B-1202
penoxsulam
H-12


B-1203
propoxycarbazone-sodium
H-12


B-1204
pyrazosulfuron-ethyl
H-12


B-1205
pyroxsulam
H-12


B-1206
rimsulfuron
H-12


B-1207
sulfosulfuron
H-12


B-1208
thiencarbazone-methyl
H-12


B-1209
tritosulfuron
H-12


B-1210
2,4-D and its salts and esters
H-12


B-1211
aminopyralid and its salts and esters
H-12


B-1212
clopyralid and its salts and esters
H-12


B-1213
dicamba and its salts and esters
H-12


B-1214
fluroxypyr-meptyl
H-12


B-1215
quinclorac
H-12


B-1216
quinmerac
H-12


B-1217
H-9
H-12


B-1218
diflufenzopyr
H-12


B-1219
diflufenzopyr-sodium
H-12


B-1220
clomazone
H-12


B-1221
diflufenican
H-12


B-1222
fluorochloridone
H-12


B-1223
isoxaflutol
H-12


B-1224
mesotrione
H-12


B-1225
picolinafen
H-12


B-1226
sulcotrione
H-12


B-1227
tefuryltrione
H-12


B-1228
tembotrione
H-12


B-1229
topramezone
H-12


B-1230
H-7
H-12


B-1231
atrazine
H-12


B-1232
diuron
H-12


B-1233
fluometuron
H-12


B-1234
hexazinone
H-12


B-1235
isoproturon
H-12


B-1236
metribuzin
H-12


B-1237
propanil
H-12


B-1238
terbuthylazine
H-12


B-1239
paraquat dichloride
H-12


B-1240
flumioxazin
H-12


B-1241
oxyfluorfen
H-12


B-1242
saflufenacil
H-12


B-1243
sulfentrazone
H-12


B-1244
H-1
H-12


B-1245
H-2
H-12


B-1246
glyphosate
H-12


B-1247
glyphosate-isopropylammonium
H-12


B-1248
glyphosate-trimesium (sulfosate)
H-12


B-1249
glufosinate
H-12


B-1250
glufosinate-ammonium
H-12


B-1251
pendimethalin
H-12


B-1252
trifluralin
H-12


B-1253
acetochlor
H-12


B-1254
cafenstrole
H-12


B-1255
dimethenamid-P
H-12


B-1256
fentrazamide
H-12


B-1257
flufenacet
H-12


B-1258
mefenacet
H-12


B-1259
metazachlor
H-12


B-1260
metolachlor-S
H-12


B-1261
pyroxasulfone
H-12


B-1262
isoxaben
H-12


B-1263
dymron
H-12


B-1264
indanofan
H-12


B-1265
oxaziclomefone
H-12


B-1266
triaziflam
H-12


B-1267
atrazine + H-1
H-12


B-1268
atrazine + glyphosate
H-12


B-1269
atrazine + mesotrione
H-12


B-1270
atrazine + nicosulfuron
H-12


B-1271
atrazine + tembotrione
H-12


B-1272
atrazine + topramezone
H-12


B-1273
clomazone + glyphosate
H-12


B-1274
diflufenican + clodinafop-propargyl
H-12


B-1275
diflufenican + fenoxaprop-P-ethyl
H-12


B-1276
diflufenican + flupyrsulfuron-methyl-sodium
H-12


B-1277
diflufenican + glyphosate
H-12


B-1278
diflufenican + mesosulfuron-methyl
H-12


B-1279
diflufenican + pinoxaden
H-12


B-1280
diflufenican + pyroxsulam
H-12


B-1281
flumetsulam + glyphosate
H-12


B-1282
flumioxazin + glyphosate
H-12


B-1283
imazapic + glyphosate
H-12


B-1284
imazethapyr + glyphosate
H-12


B-1285
isoxaflutol + H-1
H-12


B-1286
isoxaflutol + glyphosate
H-12


B-1287
metazachlor + H-1
H-12


B-1288
metazachlor + glyphosate
H-12


B-1289
metazachlor + mesotrione
H-12


B-1290
metazachlor + nicosulfuron
H-12


B-1291
metazachlor + terbuthylazine
H-12


B-1292
metazachlor + topramezone
H-12


B-1293
metribuzin + glyphosate
H-12


B-1294
pendimethalin + H-1
H-12


B-1295
pendimethalin + clodinafop-propargyl
H-12


B-1296
pendimethalin + fenoxaprop-P-ethyl
H-12


B-1297
pendimethalin + flupyrsulfuron-methyl-sodium
H-12


B-1298
pendimethalin + glyphosate
H-12


B-1299
pendimethalin + mesosulfuron-methyl
H-12


B-1300
pendimethalin + mesotrione
H-12


B-1301
pendimethalin + nicosulfuron
H-12


B-1302
pendimethalin + pinoxaden
H-12


B-1303
pendimethalin + pyroxsulam
H-12


B-1304
pendimethalin + tembotrione
H-12


B-1305
pendimethalin + topramezone
H-12


B-1306
pyroxasulfone + tembotrione
H-12


B-1307
pyroxasulfone + topramezone
H-12


B-1308
sulfentrazone + glyphosate
H-12


B-1309
terbuthylazine + H-1
H-12


B-1310
terbuthylazine + foramsulfuron
H-12


B-1311
terbuthylazine + glyphosate
H-12


B-1312
terbuthylazine + mesotrione
H-12


B-1313
terbuthylazine + nicosulfuron
H-12


B-1314
terbuthylazine + tembotrione
H-12


B-1315
terbuthylazine + topramezone
H-12


B-1316
trifluralin + glyphosate
H-12


B-1317
2-1
—


B-1318
2-2
—


B-1319
2-3
—


B-1320
2-4
—


B-1321
2-5
—


B-1322
2-6
—


B-1323
2-7
—


B-1324
2-8
—


B-1325
2-9
—


B-1326
2-1
benoxacor


B-1327
2-2
benoxacor


B-1328
2-3
benoxacor


B-1329
2-4
benoxacor


B-1330
2-5
benoxacor


B-1331
2-6
benoxacor


B-1332
2-7
benoxacor


B-1333
2-8
benoxacor


B-1334
2-9
benoxacor


B-1335
2-1
cloquintocet


B-1336
2-2
cloquintocet


B-1337
2-3
cloquintocet


B-1338
2-4
cloquintocet


B-1339
2-5
cloquintocet


B-1340
2-6
cloquintocet


B-1341
2-7
cloquintocet


B-1342
2-8
cloquintocet


B-1343
2-9
cloquintocet


B-1344
2-1
cyprosulfamide


B-1345
2-2
cyprosulfamide


B-1346
2-3
cyprosulfamide


B-1347
2-4
cyprosulfamide


B-1348
2-5
cyprosulfamide


B-1349
2-6
cyprosulfamide


B-1350
2-7
cyprosulfamide


B-1351
2-8
cyprosulfamide


B-1352
2-9
cyprosulfamide


B-1353
2-1
dichlormid


B-1354
2-2
dichlormid


B-1355
2-3
dichlormid


B-1356
2-4
dichlormid


B-1357
2-5
dichlormid


B-1358
2-6
dichlormid


B-1359
2-7
dichlormid


B-1360
2-8
dichlormid


B-1361
2-9
dichlormid


B-1362
2-1
fenchlorazole


B-1363
2-2
fenchlorazole


B-1364
2-3
fenchlorazole


B-1365
2-4
fenchlorazole


B-1366
2-5
fenchlorazole


B-1367
2-6
fenchlorazole


B-1368
2-7
fenchlorazole


B-1369
2-8
fenchlorazole


B-1370
2-9
fenchlorazole


B-1371
2-1
isoxadifen


B-1372
2-2
isoxadifen


B-1373
2-3
isoxadifen


B-1374
2-4
isoxadifen


B-1375
2-5
isoxadifen


B-1376
2-6
isoxadifen


B-1377
2-7
isoxadifen


B-1378
2-8
isoxadifen


B-1379
2-9
isoxadifen


B-1380
2-1
mefenpyr


B-1381
2-2
mefenpyr


B-1382
2-3
mefenpyr


B-1383
2-4
mefenpyr


B-1384
2-5
mefenpyr


B-1385
2-6
mefenpyr


B-1386
2-7
mefenpyr


B-1387
2-8
mefenpyr


B-1388
2-9
mefenpyr


B-1389
2-1
H-11


B-1390
2-2
H-11


B-1391
2-3
H-11


B-1392
2-4
H-11


B-1393
2-5
H-11


B-1394
2-6
H-11


B-1395
2-7
H-11


B-1396
2-8
H-11


B-1397
2-9
H-11


B-1398
2-1
H-12


B-1399
2-2
H-12


B-1400
2-3
H-12


B-1401
2-4
H-12


B-1402
2-5
H-12


B-1403
2-6
H-12


B-1404
2-7
H-12


B-1405
2-8
H-12


B-1406
2-9
H-12









The compounds of formula I and the compositions according to the invention may also have a plant-strengthening action. Accordingly, they are suitable for mobilizing the defense system of the plants against attack by unwanted microorganisms, such as harmful fungi, but also viruses and bacteria. Plant-strengthening (resistance-inducing) substances are to be understood as meaning, in the present context, those substances which are capable of stimulating the defense system of treated plants in such away that, when subsequently inoculated by unwanted microorganisms, the treated plants display a substantial degree of resistance to these microorganisms.


The compounds of formula I can be employed for protecting plants against attack by unwanted microorganisms within a certain period of time after the treatment. The period of time within which their protection is effected generally extends from 1 to 28 days, preferably from 1 to 14 days, after the treatment of the plants with the compounds of formula I, or, after treatment of the seed, for up to 9 months after sowing.


The compounds of formula I and the compositions according to the invention are also suitable for increasing the harvest yield.


Moreover, they have reduced toxicity and are tolerated well by the crop plants.







EXAMPLES

The preparation of the compounds of formula I is illustrated by examples; however, the subject matter of the present invention is not limited to the examples given. With appropriate modification of the starting materials, the procedures given in the examples below were used to obtain further compounds 1. The compounds obtained in this manner are listed in table C, together with physical data. The products shown below were characterized by determination of the melting point, NMR spectroscopy or the masses ([m/z]) determined by HPLC-MS spectrometry.


HPLC-MS: high performance liquid chromatography coupled with mass spectrometry;


MeOD: Tetradeuteromethanol


MS: Mass spectroscopy


THF: tetrahydrofuran


TFA: trifluoroacetic acid


s: singlet


d: doublet


t: triplet


m: multiplet


HPLC column: RP-18 column (Chromolith Speed ROD from Merck KgaA, Germany), 50*4.6 mm; mobile phase: acetonitrile+0.1% TFA/water+0.1% TFA, using a gradient from 5:95 to 100:0 over 5 minutes at 40° C., flow rate 1.8 mL/min.


MS: quadrupole electrospray ionization, 80 V (positive mode).


HPLC column: Luna-C18(2) 5 μm column (Phenomenex), 2.0*50 mm; mobile phase: acetonitrile+0.0625% TFA/water+0.0675% TFA, using a gradient from 10:90 to 80:20 over 4.0 minutes at 40° C., flow rate 0.8 mL/min.


MS: quadrupole electrospray ionization, 70 V (positive mode).


Example 1: 4-Bromo-3-(diethylcarbamothioylamino)-6-fluoro-2-methyl-N-(1-methyltetrazol-5-yl)benzamide (compound formula (I.A′.VII), where, R1, R2a, R2b and R3 are as defined in line 722 of table A



embedded image


Step 1: 4-Bromo-6-fluoro-3-isothiocyanato-2-methyl-N-(1-methyltetrazol-5-yl)benzamide

A solution of 3-amino-4-bromo-6-fluoro-2-methyl-N-(1-methyltetrazol-5-yl)benzamide (8.0 g, 24 mmol) in 500 ml THE was cooled to 0° C. and thiophosgene (3.2 g, 28 mmol) was added. The mixture was heated to reflux for 8 hours and stirred for additional 48 h at 22° C. The obtained crude solution of the isothiocyanate was used without further purification in step 2.


Step 2: 4-Bromo-3-(diethylcarbamothioylamino)-6-fluoro-2-methyl-N-(1-methyltetrazol-5-yl)benzamide

An aliquot of the solution of 4-bromo-6-fluoro-3-isothiocyanato-2-methyl-N-(1-methyltetrazol-5-yl)benzamide in THE (containing ca. 400 mg of the isothiocyanate, 1.08 mmol) was treated with triethylamine (218 mg) and a solution of diethylamine (79 mg) in THE (5 ml). The mixture was stirred for 4 h at 22° C. The solvent was evaporated in vacuo and the residue was dissolved in ethyl acetate. The thus obtained solution was washed with 2N aqueous hydrochloric acid and brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the remainder was purified by column chromatography to yield 164 mg of the product as a solid.



1H NMR (400 MHz, MeOD), δ 7.50 (d, 1H), 4.05 (s, 3H), 3.7-3.9 (m, 4H), 2.35 (s, 3H), 1.3 (t, 6H).


By analogy to the method described in the Example 1, the following compounds of formula (I.A.′VII) according to Table C (examples 2 to 17), compounds of formula (I.A′.VIII) according to Table D (examples 18 to 24), compounds of formula (I.A′.I) according to Table E (examples 25 to 33), compounds of formula (I.B′.VII) according to Table F (examples 34 and 35), and compounds of formula (I.D′.VII) according to Table G (examples 36 to 38) were prepared:










TABLE C








I.A′.VII




embedded image



















cpd. no
in table A
R1
R2a
R2b
R3
MS (m/z)
















1
722
CH3
CH2CH3
CH2CH3
Br
444.0


2
644
CH3
CH2CH3
CH3
Br
432.0


3
692
CH3
C6H5
CH3
Br
478.0















4
1088 
CH3


embedded image


Br
457.9
















5
932
CH3
cyclopropyl
cyclopropyl
Br
470.0


6
656
CH3
CH(CH3)2
CH3
Br
446.0


7
650
CH3
CH2CH2CH3
CH3
Br
446.0


8
746
CH3
cyclopropyl
CH2CH3
Br
456.0


9
632
CH3
2,6-(CH3)2—C6H3
H
Br
493.9


10
578
CH3
C(CH3)3
H
Br
445.9


11
608
CH3
C6H5
H
Br
447.8


12
584
CH3
cyclopropyl
H
Br
427.8


13
1454 
OCH3
phenyl
CH(CH3)2
Br
524.0


14
680
CH3
CH2CF3
CH3
Br
486.0


15
758
CH3
CH2CF3
CH2CH3
Br
500.0


16
752
CH3
CH2CHF2
CH2CH3
Br
482.0


17
674
CH3
CH2CHF2
CH3
Br
468.0

















TABLE D








I.A′.VIII




embedded image



















cpd. no
in table A
R1
R2a
R2b
R3
MS (m/z)
















18
932
CH3
cyclopropyl
cyclopropyl
Br
484.1


19
746
CH3
cyclopropyl
CH2CH3
Br
470.1


20
644
CH3
CH2CH3
CH3
Br
444.1


21
722
CH3
CH2CH3
CH2CH3
Br
460.1


22
692
CH3
phenyl
CH3
Br
492.1


23
770
CH3
phenyl
CH2CH3
Br
506.1


24
902
CH3
phenyl
CH(CH3)2
Br
520.1

















TABLE E








I.A′.I




embedded image



















cpd. no
in table A
R1
R2a
R2b
R3
MS (m/z)
















25
679
CH3
CH2CF3
CH3
Cl
422.0


26
757
CH3
CH2CF3
CH2CH3
Cl
436.0


27
673
CH3
CH2CHF2
CH3
Cl
404.0


28
751
CH3
CH2CHF2
CH2CH3
Cl
418.1


29
680
CH3
CH2CF3
CH3
Br
468.0


30
758
CH3
CH2CF3
CH2CH3
Br
482.0


31
121
Cl
CH2CHF2
CH3
Cl
424.0


32
127
Cl
CH2CF3
CH3
Cl
442.0


33
205
Cl
CH2CF3
CH2CH3
Cl
420.0

















TABLE F








I.B′.VII




embedded image



















cpd. no
in table A
R1
R2a
R2b
R3
MS (m/z)





34
722
CH3
CH2CH3
CH2CH3
Br
442.9


35
644
CH3
CH2CH3
CH3
Br
430.8

















TABLE G








I.D′.VII




embedded image



















cpd. no
in table A
R1
R2a
R2b
R3
MS (m/z)





36
722
CH3
CH2CH3
CH2CH3
Br
444.0


37
692
CH3
phenyl
CH3
Br
480.0


38
644
CH3
CH2CH3
CH3
Br
431.9









Use Examples

The herbicidal activity of the compounds of formula I was demonstrated by the following greenhouse experiments:


The culture containers used were plastic flowerpots containing loamy sand with approximately 3.0% of humus as the substrate. The seeds of the test plants were sown separately for each species.


For the pre-emergence treatment, the active ingredients, which had been suspended or emulsified in water, were applied directly after sowing by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the plants had rooted. This cover caused uniform germination of the test plants, unless this had been impaired by the active ingredients.


For the post-emergence treatment, the test plants were first grown to a height of 3 to 15 cm, depending on the plant habit, and only then treated with the active ingredients which had been suspended or emulsified in water by means of finely distributing nozzles. For this purpose, the test plants were either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment.


Depending on the species, the plants were kept at 10-25° C. or 20-25° C., respectively. The test period extended over 2 to 4 weeks. During this time, the plants were tended, and their response to the individual treatments was evaluated.


Evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the plants, or complete destruction of at least the aerial moieties, and 0 means no damage, or normal course of growth. A good herbicidal activity is given at values of at least 70 and a very good herbicidal activity is given at values of at least 85.


Test series 1:


At an application rate of 250 g/ha the following compounds were tested in post-emergence tests against:


ALOMY (Alopecurus myosuroiedes)


ECHCG (Echinocloa crus-galli)


SETFA (Setaria faberi)


In test series 1, compounds of examples 1, 2, 4, 5, 6, 7, 8, 14, 16, 17, 18, 19, 21, 25, 26, 27, 28, 29, 30, 31, 32, 33 showed >85% control of ALOMY. The compound of example 34 showed 80% control of ALOMY.


In test series 1, compounds of examples 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 36, 37 showed >85% control of ECHCG. The compound of example 34 showed 80% control of ECHCG.


In test series 1, compounds of examples 1, 2, 4, 5, 7, 8, 9, 10, 14, 16, 17, 18, 25, 26, 27, 28, 29, 30, 31, 32, 33 showed >85% control of SETFA.

Claims
  • 1. A compound of formula I,
  • 2. The compound of claim 1, where Q is Q1.
  • 3. The compound of claim 1, where Q is Q2.
  • 4. The compound of claim 1, where Q is Q4.
  • 5. The compound of claim 1, where R1 is selected from the group consisting of halogen, nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkoxy-Z1- and R1b—S(O)k—Z1-.
  • 6. The compound of claim 5, where R1 is selected from the group consisting of halogen, C1-C4-alkyl and C1-C4-alkoxy.
  • 7. The compound of claim 1, where R2a is selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-alkoxy, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, C1-C6-haloalkyl, phenyl, benzyl, and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1, 2, 3 or 4 heteroatoms as ring members which are selected from the group consisting of O, N and S, where phenyl, benzyl and heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4 groups which are identical or different and selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy; andR2b is selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, C1-C6-haloalkyl, phenyl, benzyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1, 2, 3 or 4 heteroatoms as ring members which are selected from the group consisting of O, N and S, where phenyl, benzyl and heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4 groups which are identical or different and selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy.
  • 8. The compound of claim 1, where R2a and R2b, together with the nitrogen atom to which they are bound, form a 4-, 5-, 6- or 7-membered, saturated or unsaturated heterocyclic radical which may contain as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1, 2, 3 or 4 groups which are identical or different and selected from the group consisting of ═O, OH, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy.
  • 9. The compound of claim 1, where R2a is selected from the group consisting of C1-C6-alkyl, C3-C6-cycloalkyl, C1-C4-haloalkyl and phenyl, where phenyl is unsubstituted or substituted by 1, 2, 3 or 4 C1-C4-alkyl groups which are identical or different; andR2b is selected from the group consisting of hydrogen, C1-C4-alkyl and C3-C6-cycloalkyl; orR2a and R2b, together with the nitrogen atom to which they are bound, form a 5- or 6-membered saturated heterocyclic radical which may contain as a ring member a further heteroatom selected from O, S and N, and which is unsubstituted or carries 1, 2, 3 or 4 groups R2d which are selected from the group consisting of C1-C4-alkyl and fluorinated C1-C4-alkyl.
  • 10. The compound of claim 1, where R2c is hydrogen or C1-C4-alkyl, and is in particular hydrogen.
  • 11. The compound of claim 1, having one or more of the following features i) to v): i) R3 is selected from the group consisting of halogen, nitro, C1-C6-alkyl, C1-C8-haloalkyl, C1-C8-haloalkoxy-Z3, and R3b—S(O)k—Z3;ii) R4 is hydrogen or halogen;iii) R5 is hydrogen or halogen;iv) R6a, R6b, R6c, R6d, independently of each other, are selected from the group consisting of C1-C6-alkyl, C1-C4-alkoxy-C1-C4-alkyl, and phenyl;v) R7 is hydrogen.
  • 12. The compound of claim 1, where R3 is halogen.
  • 13. The compound of claim 1, where R4 is hydrogen.
  • 14. The compound of claim 1, where R5 is hydrogen or fluorine.
  • 15. The compound of claim 1, where R6a, R6b, R6c, R6d, independently of each other, are C1-C4-alkyl.
  • 16. The compound of claim 1, where R7 is hydrogen.
  • 17. The compound of claim 1, where Z2 is covalent bond.
  • 18. The compound of claim 1, which is selected from the compounds of formulae I.A′, I.B′ and I.D′
  • 19. The compound of claim 18, where R1 is halogen, C1-C2-alkyl or C1-C2-alkoxy;R2a is selected from the group consisting of C1-C4-alkyl, C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkyl-methyl, fluorinated C1-C4-alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1, 2, 3 or 4 radicals selected from the group consisting of halogen, methyl and methoxy;R2b is selected from the group consisting of hydrogen, C1-C4-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-methyl and fluorinated C1-C4-alkyl; orR2a and R2b, together with the nitrogen atom to which they are bound, form a 5- or 6-membered saturated heterocyclic radical which is selected from the group consisting of 4-morpholinyl, 4-thiomorpholinyl, 1-piperidinyl and 1-pyrrolidinyl, where 4-morpholinyl, 4-thiomorpholinyl, 1-piperidinyl and 1-pyrrolidinyl are unsubstituted or carry 1, 2, 3 or 4 groups R2d which are selected from the group consisting of C1-C4-alkyl and fluorinated C1-C4-alkyl;R2c is selected from the group consisting of hydrogen and C1-C4-alkyl;R3 is selected from the group consisting of halogen, C1-C2-alkyl, fluorinated C1-C2-alkyl, S—C1-C2-alkyl, S(O)2—C1-C2-alkyl, S(O)2—C1-C2-alkyl, S-(fluorinated C1-C2-alkyl), S(O)-(fluorinated C1-C2-alkyl) and S(O)2-(fluorinated C1-C2-alkyl);R4 is hydrogen,R5 is hydrogen or fluorine; andR6a, R6b and R6d, independently of each other, are selected from the group consisting of C1-C4-alkyl and C1-C4-alkoxy-C1-C4-alkyl;and where in particularR1 is halogen, C1-C2-alkyl or C1-C2-alkoxy;R2a is selected from the group consisting of C1-C4-alkyl, C3-C6-cycloalkyl, fluorinated C1-C4-alkyl and phenyl which is unsubstituted or substituted by 1, 2, 3 or 4 methyl groups;R2b is selected from the group consisting of hydrogen, C1-C4-alkyl and C3-C6-cycloalkyl; orR2a and R2b, together with the nitrogen atom to which they are bound, form a 4-morpholinyl ring;R2c is hydrogen;R3 is halogen;R4 is hydrogen,R5 is hydrogen or fluorine; andR6a, R6b and R6d, independently of each other, are C1-C4-alkyl.
  • 20. A composition comprising at least one compound as claimed in claim 1, an N-oxide or an agriculturally suitable salt thereof, and at least one auxiliary, which is customary for formulating crop protection compounds.
  • 21. (canceled)
  • 22. A method for controlling unwanted vegetation comprising allowing a herbicidally effective amount of at least one compound as claimed in claim 1 to act on plants, their seed, and/or their habitat.
Priority Claims (1)
Number Date Country Kind
18150628.8 Jan 2018 EP regional
PCT Information
Filing Document Filing Date Country Kind
PCT/EP2019/050232 1/7/2019 WO 00