WO2019016385A1

WO2019016385A1 - Benzamide compounds and their use as herbicides

Info

Publication number: WO2019016385A1
Application number: PCT/EP2018/069807
Authority: WO
Inventors: Thomas Zierke; Markus Kordes; Thomas Seitz; Ryan Louis NIELSON
Original assignee: Basf Se
Priority date: 2017-07-21
Filing date: 2018-07-20
Publication date: 2019-01-24
Also published as: AR112342A1

Abstract

The present invention relates to benzamide compounds of the formula (I) and the N-oxides and salts thereof and to compositions comprising the same. The variables are as defined in the claims and the description. The invention also relates to the use of the benzamide compounds or of the compositions comprising such compounds for controlling unwanted vegetation. Furthermore, the invention relates to methods of applying such compounds.

Description

Benzamide compounds and their use as herbicides Description The present invention relates to benzamide compounds and salts thereof and to compositions comprising the same. The invention also relates to the use of the benzamide compounds or 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 ongo- ing need for new herbicides which have high activities and selectivities together with a substantial lack of toxicity for humans and animals.

WO 201 1/035874 describes N-(1 ,2,5-oxadizol-3-yl)benzamides carrying 3 substituents in the 2-, 3- and 4-positions of the phenyl ring and their use as herbicides.

WO 2013/072300 describes N-(1 ,2,5-oxadizol-3-yl)benzamides carrying up to 5 substitu- ents at the phenyl ring and their use as herbicides.

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

WO 2013/017559 describes N-(tetrazol-4-yl)- and N-(triazol-3-yl)arylcarboxylic acid am- ides carrying substituents in the 2- and 4-positions of the aryl ring, relative to the 1 -position of the carboxamide group, and their use as herbicides.

WO 2013/064457 describes N-(tetrazol-4-yl)- and N-(triazol-3-yl)arylcarboxylic acid amides carrying 3 substituents in the 2-, 4- and 5-positions of the aryl ring and their use as herbicides.

WO 2013/083859 describes N-(tetrazol-4-yl)- and N-(triazol-3-yl)benzamides carrying up to 5 substituents at the phenyl ring and their use as herbicides.

WO 2013/124245 describes N-(tetrazol-5-yl)-, N-(triazol-3-yl)- and N-(1 ,3,4-oxadiazolyl)- arylcarboxylic acid amides carrying a nitro group in 4-position of the aryl ring, relative to the 1 - position of the carboxamide group, and a substituent in the 2-position, and their use as herbi- cides.

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 com- pounds 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 and their agriculturally suitable salts. Therefore, in a first aspect the present invention relates to compounds of formula I, the N- oxides or agriculturally suitable salts thereof,

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

(Q¹) (Q²) (Q³) (Q⁴) 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, Ci-Cs-alkyl, C2-C8- alkenyl, C2-Cs-alkynyl, Ci-Cs-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy- Ci-C₄-alkyl, Ci-C₈-alkoxy, Ci-C₄-alkoxy-Ci-C₄-alkoxy-Z¹, Ci-C₆-haloalkoxy, R^1b- S(0)_k-Zⁱ;

R² is a radical of the formul

where # in formulae 2a and 2b indicates the point of attachment to the oxygen atom bearing R²;

R³ is selected from the group consisting of hydrogen, cyano, thiocyanato, halogen, nitro, hydroxy-Z³, Ci-C6-alkyl, C2-Cs-alkenyl, C2-Cs-alkynyl, C3-Cio-cycloalkyl-Z³, C3- C6-cycloalkenyl-Z³, C3-Cio-cycloalkoxy-Z³, C3-Cio-cycloalkyl-Ci-C2-alkoxy, where the cyclic groups of the four aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C4-cyanoalkyl, Ci-Cs-haloalkyl, C2-C8-haloalkenyl, C3- Cs-haloalkynyl, Ci-Cs-alkoxy-Z³, d-Cs-haloalkoxy-Z³, Ci-C4-alkoxy-Ci-C4-alkoxy-Z³, Ci-C4-haloalkoxy-Ci-C4-alkoxy-Z³, C2-C8-alkenyloxy-Z³, C2-C8-alkynyloxy-Z³, C₂-Cs- haloalkenyloxy-Z³, C₃-C₈-haloalkynyloxy-Z³, R^3b-S(0)_k-Z³, R^3c-C(0)-Z³, R^3dO-C(0)- Z³, R^3dO-N=CH-Z³, R^3eR^3fN-C(0)-Z³, R¾R^3hN-Z³, R²²C(0)0-Z³, R²⁵OC(0)0-Z³, (R²²)₂NC(0)0-Z³, R²⁵S(0)₂0-Z³, R²²OS(0)₂-Z³, (R²²)₂NS(0)₂-Z³, R²⁵OC(0)N(R²²)-Z³, (R²²)₂NC(0)N(R²²)-Z³, (R²²)₂NS(0)₂N(R²²)-Z³, (OH)₂P(0)-Z³, (Ci-C₄-alkoxy)₂P(0)-Z³, phenyl-Z^3a, heterocyclyl-Z^3a, 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 cyclic groups in phenyl-Z^3a and heterocyclyl-Z^3a are unsubstituted or substituted by 1 , 2, 3 or 4 groups R²¹, which are identical or different; is selected from the group consisting of hydrogen, halogen, cyano-Z¹, Ci-Cs-alkyl, ni- tro, C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C₄-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halo- genated, C₂-Cs-alkenyl, C₂-Cs-alkynyl, Ci-Cs-haloalkyl, Ci-C3-alkylamino, C1-C3- dialkylamino, Ci-C3-alkylamino-S(0)k, Ci-C3-alkylcarbonyl, d-Cs-alkoxy, C1-C4- alkoxy-Ci-C₄-alkyl, Ci-C₄-alkoxy-Ci-C₄-alkoxy-Z¹, Ci-C₄-alkylthio-Ci-C₄-alkylthio-Z¹, C₂-C6-alkenyloxy, C₂-C6-alkynyloxy, C C₆-haloalkoxy, Ci-C₄-haloalkoxy-Ci-C₄-alkyl, Ci-C₄-haloalkoxy-Ci-C₄-alkoxy-Z¹, R^1b-S(0)_k-Z¹, phenoxy-Z¹ and heterocyclyloxy-Z¹, where heterocydyloxy 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 heterocydyloxy are unsubstituted or substituted by 1 , 2, 3 or 4 groups R¹¹, which are identical or different; is halogen, cyano-Z¹-, nitro, Ci-Cs-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C₄- alkyl, where the C₃-C₇-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C₂-Cs-alkenyl, C₂-Cs-alkynyl, Ci- Cs-haloalkyl, Ci-C3-alkylamino, Ci-C3-dialkylamino, Ci-C3-alkylamino-S(0)k, C1-C3- alkylcarbonyl, Ci-Cs-alkoxy, Ci-C₄-alkoxy-Ci-C₄-alkyl, Ci-C₄-alkoxy-Ci-C₄-alkoxy- Z¹-, Ci-C₄-alkylthio-Ci-C₄-alkyl, Ci-C₄-alkylthio-Ci-C₄-alkylthio-Z¹-, C₂-C₆-alkenyloxy, C₂-C6-alkynyloxy, C C₆-haloalkoxy, Ci-C₄-haloalkoxy-Ci-C₄-alkyl, Ci-C₄-haloalkoxy- Ci-C₄-alkoxy-Z¹-, R^1b-S(0)_k-Z¹-, phenoxy-Z¹- and heterocyclyloxy-Z¹-, where heterocydyloxy is an 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 heterocydyloxy are unsubstituted or substituted by 1 , 2, 3 or 4 groups R¹¹, which are identical or different;

R^6b, R^6c, R^6d are, independently of each other,selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, where the C3- C7-cycloalkyl groups of the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C2-C6- haloalkenyl, C3-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4- alkyl, R^b-S(0)_n-Ci-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, C C₄-alkyl, C C4-haloalkyl, C C₄- alkoxy and

, R²¹ independently of each other are selected from the group consisting of cyano, halogen, nitro, Ci-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-halocycloalkyl, Ci-C₆-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C6-alkoxy, Ci- C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, Ci- C₄-alkoxy-Ci-C₄-alkoxy, C₃-C₇-cycloalkoxy and Ci-C₆-haloalkoxy, or two radicals R21 bound to the same carbon atom together may form a group =0; is a covalent bond or linear Ci-C4-alkanediyl,

Z³ independently of each other are selected from the group consisting of a covalent bond and Ci-C4-alkanediyl, which is unsubstituted, partly or completely fluorinated; is a covalent bond or a bivalent radical selected from Ci-C4-alkanediyl and C1-C4- alkanediyl-0-Ci-C4-alkanediyl,

where in the last two mentioned radicals the Ci-C4-alkanediyl groups are linear and unsubstituted, or partly or completely fluorinated or substituted by 1 , 2, 3 or 4 groups z, is selected from the group consisting of a covalent bond, Ci-C4-alkanediyl, O-C1-C4- alkanediyl, Ci-C4-alkanediyl-0 and Ci-C4-alkanediyl-0-Ci-C4-alkanediyl; are identical or different and selected from the group consisting of Ci-C6-alkyl, C3-C7- cycloalkyl, C₃-C₇-cycloalkyl-Ci-C4-alkyl, where the C₃-C₇-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C6-haloalkyl, Ci-C6-alkoxy, C2-C6-alkenyl, Ci-C4-alkyl-C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkyl- S(0)_n-Ci-C4-alkyl, Ci-C4-alkylamino-Ci-C4-alkyl, Ci-C4-dialkylamino-Ci-C4-alkyl, Ci- 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, Ci-C₄-alkyl, Ci-C₄-haloalkyl, Ci-C₄-alkoxy and Ci-C₄-haloalkoxy;

R^2a is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, C3- C₇-cycloalkyl-Ci-C₄-alkyl, where the C₃-C₇-cycloalkyl groups in the two

aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C6-haloalkyl, Ci-C6-alkoxy, C2-C6-alkenyl, Ci-C₄-alkyl-C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C₄-alkoxy-Ci-C₄-alkyl,

Ci-C₄-alkyl-S(0)_n-Ci-C₄-alkyl, Ci-C₄-alkylamino-Ci-C₄-alkyl, Ci-C₄-dialkylamino-Ci- C₄-alkyl, Ci-C₆-cyanoalkyl, R^3c-C(0)-Ci-C₄-alkyl, R^MO-C(0)-Ci-C₄-alkyl, R^3eR^3fN-

C(0)-Ci-C₄-alkyl, R^3eR^3fNS(0)₂-Ci-C₄-alkyl, 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 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, Ci-C₄-alkyl, Ci-C₄-haloalkyl, Ci- C₄-alkoxy and Ci-C₄-haloalkoxy; R^2b is selected from the group consisting of hydrogen, d-Ce-alkyl, C3-C₇-cycloalkyl, C3-

C₇-cycloalkyl-Ci-C₄-alkyl, where the C₃-C₇-cycloalkyl groups in the two

Ci-C₄-alkyl-S(0)_n-Ci-C₄-alkyl, Ci-C₄-alkylamino-Ci-C₄-alkyl, Ci-C₄-dialkylamino-Ci-

C₄-alkyl, Ci-C₆-cyanoalkyl, R^3c-C(0)-Ci-C₄-alkyl, R^3dO-C(0)-Ci-C₄-alkyl, R^3eR^3fN- C(0)-Ci-C₄-alkyl, R^3eR^3fNS(0)₂-Ci-C₄-alkyl, 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 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, Ci-C₄-alkyl, Ci-C₄-haloalkyl, Ci- C₄-alkoxy and Ci-C₄-haloalkoxy; or

R^2a, R^2b together with the nitrogen atom, to which they are bound may form a 4-, 5-, 6-, 7- or 8-membered, saturated or partially unsaturated heteromonocyclic radical or may form a 6-, 7-, 8-, 9- or 10-membered, saturated or partially unsaturated heterobicyclic radical , where the heteromono- or heterobicyclic radical may contain as a ring member a further heteroatom selected from O, S and N and where the heteromono- or heterobicyclic radical is unsubstituted or carries 1 , 2, 3 or 4 groups R^2e or carries 1 group R^z and 0, 1 , 2 or 3 groups R^2e, R^2c is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, C3- C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated,

Ci-C6-haloalkyl, Ci-C6-alkoxy, C2-C6-alkenyl, Ci-C4-alkyl-C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl,

Ci-C4-alkyl-S(0)_n-Ci-C4-alkyl, Ci-C4-alkylamino-Ci-C4-alkyl, Ci-C4-dialkylamino-Ci- C₄-alkyl, Ci-C₆-cyanoalkyl, R^3c-C(0)-Ci-C₄-alkyl, R^3dO-C(0)-Ci-C₄-alkyl, R^3eR^3fN- C(0)-Ci-C₄-alkyl, R^3eR^3fNS(0)₂-Ci-C₄-alkyl, phenyl, benzyl, heterocyclyl and heter- ocyclylmethyl, 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 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, Ci-C₄-alkyl, Ci-C₄-haloalkyl, C₁-C4- alkoxy and Ci-C4-haloalkoxy;

R^2d can be bound to each saturated carbon atom of the radical of formula 2b and is selected from the group consisting of halogen, Ci-C4-alkyl and C|-C₄-haloalkyl;

R^2e are identical or different and selected from the group consisting of halogen, CN, Ci- C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;

R^2f is selected from the group consisting of =0, R^4b-S(0)_k-Z⁴-, R^4c-C(0)-Z⁴-,

R^4dO-C(0)-Z⁴-, R^4eR^4fN-C(0)-Z⁴-,

and R^4eR^4fNS(0)₂-Z⁴-; where Z⁴ is a covalent bond or linear Ci-C4-alkanediyl;

R^b, R^1b, R^3b, R^4b independently of each other are selected from the group consisting of Ci-C6-alkyl, C3-C7-cycloalkyl, Ci-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, Ci-C₄-alkyl, Ci-C₄-haloalkyl, Ci-C₄-alkoxy and Ci-C4-haloalkoxy;

R^4c independently of each other are selected from the group consisting of hydrogen, Ci-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-Ci-C₄-alkyl, where the C₃- C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, d-Ce-haloalkyl, Ci-C₆-alkoxy, C₂-C₆-alkenyl, Ci-C₄-alkyl- C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C₄-alkoxy-Ci- C₄-alkyl, Ci-C₄-alkyl-S(0)_n-Ci-C₄-alkyl, Ci-C₄-alkylamino-Ci-C₄-alkyl, Ci-C₄- dialkylamino-Ci-C₄-alkyl, Ci-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, Ci-C₄-alkyl, Ci-C₄-haloalkyl, Ci-C₄-alkoxy and Ci-C₄-haloalkoxy;

R^3d, R^4d independently of each other are selected from the group consisting of hydrogen, Ci-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-Ci-C₄-alkyl, where the C₃- C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C-i-Ce-haloalkyl, Ci-C₆-alkoxy, C₂-C₆-alkenyl, Ci-C₄-alkyl-

C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C₄-alkoxy-Ci- C₄-alkyl, Ci-C₄-alkyl-S(0)_n-Ci-C₄-alkyl, Ci-C₄-alkylamino-Ci-C₄-alkyl, Ci-C₄- dialkylamino-Ci-C₄-alkyl, Ci-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, Ci-C₄-alkyl, Ci-C₄- haloalkyl, Ci-C₄-alkoxy and Ci-C₄-haloalkoxy;

R^3e, R^3f, R^4e, R^4f independently of each other are selected from the group consisting of hydrogen, Ci-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-Ci-C₄-alkyl, where the C₃- C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C-i-Ce-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆- alkynyl, C₃-C6-haloalkynyl, Ci-C₄-alkoxy-Ci-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, Ci-C₄-alkyl, Ci-C₄-haloalkyl, Ci-C₄-alkoxy and Ci-C₄-haloalkoxy; or

R^3eand R^3f or R^4e and R^4f 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 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 =0, halogen, Ci-C₄-alkyl, Ci-C₄- haloalkyl, Ci-C₄-alkoxy and Ci-C₄-haloalkoxy;

R¾, R⁴9 independently of each other are selected from the group consisting of hydrogen, Ci-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-Ci-C₄-alkyl, where the C₃-

C₇-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-Ce-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆- alkynyl, C3-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-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, Ci-C₄-alkyl, Ci-C₄-haloalkyl, Ci-C₄-alkoxy and Ci- C4-haloalkoxy;

R^3h, R^4h independently of each other are selected from the group consisting of hydrogen, d-Ce-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-Ci-C₄-alkyl, where the C₃- C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆- alkynyl, C3-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylsulfonyl, C1-C4- alkylcarbonyl, a radical C(0)R^k, 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, Ci-C₄-alkyl, Ci-C₄-haloalkyl, Ci- C4-alkoxy and Ci-C4-haloalkoxy; or

R¾ and R^3h or R⁴9 and R^4h 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 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 =0, halogen, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;

R²² is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-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-Ci-C6-alkyl, Ci-C6-alkoxy-Ci- C6-alkyl, C3-C6-cycloalkyl-Ci-C6-alkoxy-Ci-C6-alkyl, phenyl-Z¹, phenyl-0-Ci-C6-alkyl, phenyl-N(R²³)-Ci-Ce-alkyl, phenyl-S(0)_n-Ci-C6-alkyl, heterocyclyl-Z¹, heterocyclyl- N(R²³)-Ci-C₆-alkyl, heterocyclyl-0-Ci-C₆-alkyl, heterocyclyl-S(0)_n-Ci-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, 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, Ci-C6-alkyl, Ci-C₆-haloalkyl, C₃-C₆-cycloalkyl, C(0)OR²³, C(0) N(R²³)₂, OR²³, N(R²³)₂, S(0)_nR²⁴, S(0)₂OR²³, S(0)₂N(R²³)₂, and R²³0-Ci-C₆-alkyl, and where heterocyclyl bears 0, 1 or 2 oxo groups; is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C₂- C6-alkenyl, C₂-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, and phenyl; R²⁴ is selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, and phenyl;

R²⁵ is selected from the group consisting of Ci-C6-alkyl, Ci-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-Ci-C6-alkyl, Ci-C6-alkoxy-Ci-C6- alkyl, C3-C6-cycloalkyl-Ci-C6-alkoxy-Ci-C6-alkyl, phenyl-Z¹, phenyl-0-Ci-C6-alkyl, phenyl-N(R²³)-Ci-C6-alkyl, phenyl-S(0)_n-Ci-C6-alkyl, heterocyclyl-Z¹, heterocyclyl- N(R²³)-Ci-C₆-alkyl, heterocyclyl-O-Ci-Ce-alkyl, heterocyclyl-S(0)_n-Ci-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, 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, Ci-C₆-alkyl, Ci-C₆-haloalkyl, C₃-C₆-cycloalkyl, C(0)OR²³, C(0)N(R²³)₂, OR²³, N(R²³)₂, S(0)_nR²⁴, S(0)₂OR²³, S(0)₂N(R²³)₂, and R²³0-Ci-C₆-alkyl, and where heterocyclyl bears 0, 1 or 2 oxo groups; k is 0, 1 or 2; n is 0, 1 or 2; p is 0, 1 or 2; and

R^k has the meanings of R^3c.

In a particular embodiment, the present invention relates to compounds of formula I, the N-oxides or agriculturally suitable salts thereof,

wherein

(Q¹) (Q²) (Q³) (Q⁴) where # in formulae Q¹, Q², Q³ and Q⁴ indicates the point of attachment to the nitrogen atom; is selected from the group consisting of cyano, halogen, nitro, Ci-Cs-alkyl, C2-C8- alkenyl, C2-C8-alkynyl, Ci-Cs-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy- Ci-C₄-alkyl, Ci-C₈-alkoxy, Ci-C₄-alkoxy-Ci-C₄-alkoxy-Z¹ , Ci-C₆-haloalkoxy, R^{1 b}-

is a radical of the formulae 2a or 2b;

where # in formulae 2a and 2b indicates the point of attachment to the oxygen atom bearing R²; R³ is selected from the group consisting of hydrogen, cyano, thiocyanato, halogen, nitro, hydroxy-Z³, Ci-C6-alkyl, C2-Cs-alkenyl, C2-Cs-alkynyl, C3-Cio-cycloalkyl-Z³, C3- C6-cycloalkenyl-Z³, C3-Cio-cycloalkoxy-Z³, C3-Cio-cycloalkyl-Ci-C2-alkoxy, where the cyclic groups of the four aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C4-cyanoalkyl, Ci-Cs-haloalkyl, C2-C8-haloalkenyl, C3- Cs-haloalkynyl, Ci-Cs-alkoxy-Z³, d-Cs-haloalkoxy-Z³, Ci-C4-alkoxy-Ci-C4-alkoxy-Z³,

Ci-C4-haloalkoxy-Ci-C4-alkoxy-Z³, C2-C8-alkenyloxy-Z³, C2-C8-alkynyloxy-Z³, C2-C8- haloalkenyloxy-Z³, C₃-C₈-haloalkynyloxy-Z³, R^3b-S(0)_k-Z³, R^3c-C(0)-Z³, R^3dO-C(0)- Z³, R^3dO-N=CH-Z³, R^3eR^3fN-C(0)-Z³, R¾R³hN-Z³, R²²C(0)0-Z³, R²⁵OC(0)0-Z³, (R²²)₂NC(0)0-Z³, R²⁵S(0)₂0-Z³, R²²OS(0)₂-Z³, (R²²)₂NS(0)₂-Z³, R²⁵OC(0)N (R²²)-Z³, (R²²)₂NC(0) N(R²²)-Z³, (R²²)₂NS(0)₂N(R²²)-Z³, (OH)₂P(0)-Z³, (Ci-C₄-alkoxy)₂P(0)-Z³, phenyl-Z^3a, heterocyclyl-Z^3a, 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 cyclic groups in phenyl-Z^3a and heterocyclyl-Z^3a 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, Ci-Cs-alkyl, ni- tro, C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halo- genated, C2-C8-alkenyl, C2-C8-alkynyl, Ci-Cs-haloalkyl, Ci-C3-alkylamino, C1-C3- dialkylamino, Ci-C3-alkylamino-S(0)k, Ci-C3-alkylcarbonyl, Ci-Cs-alkoxy, C1-C4- alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy-Z¹, Ci-C4-alkylthio-Ci-C4-alkylthio-Z¹, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C C₆-haloalkoxy, Ci-C4-haloalkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C₄-alkoxy-Z¹, R^1b-S(0)_k-Z¹, phenoxy-Z¹ and heterocyclyloxy-Z¹, where heterocydyloxy 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 heterocydyloxy are unsubstituted or substituted by 1 , 2, 3 or 4 groups R¹¹, which are identical or different; R⁵ is halogen, cyano-Z¹-, nitro, Ci-Cs-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C4- alkyl, where the C₃-C₇-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C2-Cs-alkenyl, C2-Cs-alkynyl, Ci- Cs-haloalkyl, Ci-C3-alkylamino, Ci-C3-dialkylamino, Ci-C3-alkylamino-S(0)k, C1-C3- alkylcarbonyl, Ci-Cs-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy- Z¹-, Ci-C₄-alkylthio-Ci-C₄-alkyl, Ci-C₄-alkylthio-Ci-C₄-alkylthio-Z¹-, C₂-C₆-alkenyloxy,

C2-C6-alkynyloxy, C C₆-haloalkoxy, Ci-C4-haloalkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy- Ci-C₄-alkoxy-Z¹-, R^1b-S(0)_k-Z¹-, phenoxy-Z¹- and heterocyclyloxy-Z¹-, where heterocydyloxy is an 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 heterocydyloxy are unsubstituted or substituted by 1 , 2, 3 or 4 groups R¹¹, which are identical or different; R^6a, R^6b, R^6c, R^6d are, independently of each other,selected from the group consisting of

Ci-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7- cycloalkyl groups of the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C2-C6- haloalkenyl, C3-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4- alkyl, R^b-S(0)_n-Ci-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, C C₄-alkyl, C C4-haloalkyl, C C₄- alkoxy and

, R²¹ independently of each other are selected from the group consisting of cyano, halogen, nitro, Ci-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-halocycloalkyl, Ci-C₆-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C6-alkoxy, Ci C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, Ci- C₄-alkoxy-Ci-C₄-alkoxy, C₃-C₇-cycloalkoxy and Ci-C₆-haloalkoxy, or two radicals R²ⁱ bound to the same carbon atom together may form a group =0; Z is a covalent bond or linear Ci-C4-alkanediyl,

Z¹, Z³ independently of each other are selected from the group consisting of a covalent bond and Ci-C4-alkanediyl, which is unsubstituted, partly or completely fluorinated; Z² is a covalent bond or a bivalent radical selected from Ci-C4-alkanediyl and C1-C4- alkanediyl-0-Ci-C4-alkanediyl,

where in the last two mentioned radicals the Ci-C4-alkanediyl groups are linear and unsubstituted, or partly or completely fluorinated or substituted by 1 , 2, 3 or 4 groups z,

Z^3a is selected from the group consisting of a covalent bond, Ci-C4-alkanediyl, O-C1-C4- alkanediyl, Ci-C4-alkanediyl-0 and Ci-C4-alkanediyl-0-Ci-C4-alkanediyl;

R^z are identical or different and selected from the group consisting of Ci-C6-alkyl, C3-C7- cycloalkyi, C₃-C₇-cycloalkyl-Ci-C4-alkyl, where the C₃-C₇-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C6-haloalkyl, Ci-C6-alkoxy, C2-C6-alkenyl, Ci-C4-alkyl-C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkyl- S(0)_n-Ci-C4-alkyl, Ci-C4-alkylamino-Ci-C4-alkyl, Ci-C4-dialkylamino-Ci-C4-alkyl, Ci- 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, Ci-C₄-alkyl, Ci-C₄-haloalkyl, Ci-C₄-alkoxy and Ci-C4-haloalkoxy;

aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C6-haloalkyl, Ci-C6-alkoxy, C2-C6-alkenyl, Ci-C4-alkyl-C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl,

Ci-C4-alkyl-S(0)_n-Ci-C4-alkyl, Ci-C4-alkylamino-Ci-C4-alkyl, Ci-C4-dialkylamino-Ci- C₄-alkyl, Ci-C₆-cyanoalkyl, R^3c-C(0)-Ci-C₄-alkyl, R^3dO-C(0)-Ci-C₄-alkyl, R^3eR^3fN-

C(0)-Ci-C₄-alkyl, R^3eR^3fNS(0)₂-Ci-C₄-alkyl, 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 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, Ci-C₄-alkyl, Ci-C₄-haloalkyl, Ci- C₄-alkoxy and Ci-C₄-haloalkoxy;

R^2b is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, C3- C₇-cycloalkyl-Ci-C₄-alkyl, where the C₃-C₇-cycloalkyl groups in the two

Ci-C₄-alkyl-S(0)_n-Ci-C₄-alkyl, Ci-C₄-alkylamino-Ci-C₄-alkyl, Ci-C₄-dialkylamino-Ci- C₄-alkyl, Ci-C₆-cyanoalkyl, R^3c-C(0)-Ci-C₄-alkyl, R^MO-C(0)-Ci-C₄-alkyl, R^3eR^3fN- C(0)-Ci-C₄-alkyl, R^3eR^3fNS(0)₂-Ci-C₄-alkyl, 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 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, Ci-C₄-alkyl, Ci-C₄-haloalkyl, Ci- C₄-alkoxy and Ci-C₄-haloalkoxy; or

R^2a, R^2b 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 O, S and N and where the heterocyclic radical is unsubstituted or carries 1 , 2, 3 or 4 groups R^2e or carries 1 group R^z and 0, 1 , 2 or 3 groups R^2e,

R^2c is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, C3- C₇-cycloalkyl-Ci-C₄-alkyl, where the C₃-C₇-cycloalkyl groups in the two

Ci-C₄-alkyl-S(0)_n-Ci-C₄-alkyl, Ci-C₄-alkylamino-Ci-C₄-alkyl, Ci-C₄-dialkylamino-Ci- C₄-alkyl, Ci-C₆-cyanoalkyl, R^3c-C(0)-Ci-C₄-alkyl, R^3dO-C(0)-Ci-C₄-alkyl, R^3eR^3fN- C(0)-Ci-C₄-alkyl, R^3eR^3fNS(0)₂-Ci-C₄-alkyl, 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 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, Ci-C₄-alkyl, Ci-C₄-haloalkyl, Ci- C₄-alkoxy and Ci-C₄-haloalkoxy;

R^2d can be bound to each saturated carbon atom of the radical of formula 2b and is selected from the group consisting of halogen, Ci-C₄-alkyl and Ci-C₄-haloalkyl;

R^2e are identical or different and selected from the group consisting of halogen, CN , Ci- C₄-alkyl, Ci-C₄-haloalkyl, Ci-C₄-alkoxy and Ci-C₄-haloalkoxy; R^2f is selected from the group consisting of =0, R^4b-S(0)k-Z⁴-, R^4c-C(0)-Z⁴-,

R^4dO-C(0)-Z⁴-, R^4eR^4fN-C(0)-Z⁴-,

and R^4eR^4fNS(0)₂-Z⁴-;

R^b, R^{1 b}, R^3b, R^4b independently of each other are selected from the group consisting of Ci-C6-alkyl, C3-C7-cycloalkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2- Ce-alkynyl, C₃-Ce-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, Ci-C₄-alkyl, Ci-C₄-haloalkyl, Ci-C₄-alkoxy and

Ci-C₄-haloalkoxy;

R^3c, R^4c independently of each other are selected from the group consisting of hydrogen, Ci-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-Ci-C₄-alkyl, where the C₃- C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C₆-haloalkyl, Ci-C₆-alkoxy, C₂-C₆-alkenyl, Ci-C₄-alkyl- C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C₄-alkoxy-Ci- C₄-alkyl, Ci-C₄-alkyl-S(0)_n-Ci-C₄-alkyl, Ci-C₄-alkylamino-Ci-C₄-alkyl, Ci-C₄- dialkylamino-Ci-C₄-alkyl, Ci-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, Ci-C₄-alkyl, Ci-C₄-haloalkyl, Ci-C₄-alkoxy and Ci-C₄-haloalkoxy;

R^3d, R^4d independently of each other are selected from the group consisting of hydrogen, Ci-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-Ci-C₄-alkyl, where the C₃- C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C₆-haloalkyl, Ci-C₆-alkoxy, C₂-C₆-alkenyl, Ci-C₄-alkyl-

C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C₃-C6-haloalkynyl, Ci-C₄-alkoxy-Ci- C₄-alkyl, Ci-C₄-alkyl-S(0)_n-Ci-C₄-alkyl, Ci-C₄-alkylamino-Ci-C₄-alkyl, Ci-C₄- dialkylamino-Ci-C₄-alkyl, Ci-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, Ci-C₄-alkyl, Ci-C₄- haloalkyl, Ci-C₄-alkoxy and Ci-C₄-haloalkoxy;

R^3e, R^3f, R^4e, R^4f independently of each other are selected from the group consisting of hydrogen, Ci-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-Ci-C₄-alkyl, where the C₃- C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆- alkynyl, C3-C6-haloalkynyl, Ci-C₄-alkoxy-Ci-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, Ci-C₄-alkyl, Ci-C₄-haloalkyl, Ci-C₄-alkoxy and Ci-C₄-haloalkoxy; or R^3eand R^3f or R^4e and R^4f 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 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 =0, halogen, Ci-C₄-alkyl, Ci-C₄- haloalkyl, Ci-C₄-alkoxy and Ci-C₄-haloalkoxy;

R¾, R⁴9 independently of each other are selected from the group consisting of hydrogen, Ci-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-Ci-C₄-alkyl, where the C₃- C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆- alkynyl, C₃-C6-haloalkynyl, Ci-C₄-alkoxy-Ci-C₄-alkyl, Ci-C₄-alkylsulfonyl, Ci-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, Ci-C₄-alkyl, Ci-C₄-haloalkyl, Ci-C₄-alkoxy and Ci- C₄-haloalkoxy;

R^3h, R^4h independently of each other are selected from the group consisting of hydrogen, Ci-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-Ci-C₄-alkyl, where the C₃- C₇-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆- alkynyl, C₃-C6-haloalkynyl, Ci-C₄-alkoxy-Ci-C₄-alkyl, Ci-C₄-alkylsulfonyl, Ci-C₄- alkylcarbonyl, a radical C(0)R^k, 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, Ci-C₄-alkyl, Ci-C₄-haloalkyl, Ci- C₄-alkoxy and Ci-C₄-haloalkoxy; or

R²² is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-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-Ci-C6-alkyl, Ci-C6-alkoxy-Ci- Ce-alkyl, Cs-Ce-cycloalkyl-Ci-Ce-alkoxy-d-Ce-alkyl, phenyl-Z¹, phenyl-O-d-Ce-alkyl, phenyl-N(R²³)-Ci-Ce-alkyl, phenyl-S(0)_n-Ci-C6-alkyl, heterocyclyl-Z¹, heterocyclyl- N(R²³)-Ci-C₆-alkyl, heterocyclyl-O-Ci-Ce-alkyl, heterocyclyl-S(0)_n-Ci-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, 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, Ci-Ce-alkyl, Ci-C₆-haloalkyl, C₃-C₆-cycloalkyl, C(0)OR²³, C(0)N(R²³)₂, OR²³, N(R²³)₂, S(0)_nR²⁴, S(0)₂OR²³, S(0)₂N(R²³)₂, and R²³0-Ci-C₆-alkyl, and where heterocyclyl bears 0, 1 or 2 oxo groups;

R²³ is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2- C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, and phenyl; R²⁴ is selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl,

C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, and phenyl;

R²⁵ is selected from the group consisting of Ci-C6-alkyl, Ci-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-Ci-C6-alkyl, Ci-C6-alkoxy-Ci-C6- alkyl, C3-C6-cycloalkyl-Ci-C6-alkoxy-Ci-C6-alkyl, phenyl-Z¹, phenyl-0-Ci-C6-alkyl, phenyl-N(R²³)-Ci-Ce-alkyl, phenyl-S(0)_n-Ci-C6-alkyl, heterocyclyl-Z¹, heterocyclyl- N(R²³)-Ci-C₆-alkyl, heterocyclyl-O-Ci-Ce-alkyl, heterocyclyl-S(0)_n-Ci-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, 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, Ci-Ce-alkyl, Ci-C₆-haloalkyl, C₃-C₆-cycloalkyl, C(0)OR²³, C(0)N(R²³)₂, OR²³, N(R²³)₂, S(0)_nR²⁴, S(0)₂OR²³, S(0)₂N(R²³)₂, and R²³0-Ci-C₆-alkyl, and where heterocyclyl bears 0, 1 or 2 oxo groups; k is 0, 1 or 2; n is 0, 1 or 2; p is 0, 1 or 2; and

R^k has the meanings of R^3c.

The compounds of the present invention, i.e. the compounds of formula I, their N-oxides and agriculturally suitable salts, are particularly useful for controlling unwanted vegetation.

Therefore, the invention also relates to the use of a compound of formula I, an N-oxide or an agriculturally suitable salt thereof or of a composition comprising at least one compound of formula I, an N-oxide 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, an N-oxide 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 substitution pattern, the compounds of formula I may have one or more centers of chirality, in which case they are present as mixtures of enantiomers or 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, ni- trogen-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).

Depending on the substitution pattern, the compounds of formula I may be present in the form of their tautomers. Hence the invention also relates to the tautomers of compounds of for- mula I and the stereoisomers and salts of said tautomers.

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 nonradioactive isotope (e.g., hydrogen by deuterium, ¹²C by ¹³C, ¹⁴N by ¹⁵N, ¹⁶0 by ¹⁸0) 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 term N-oxides relates to a form of compounds I in which at least one nitrogen atom is present in oxidized form (as NO). To be more precise, it relates to any compound of the present invention which has at least one tertiary nitrogen atom that is oxidized to an N-oxide moiety. N- oxides of compounds I can for example be prepared by oxidizing e.g. a tertiary ring nitrogen atom of the ring Q, and/or of any nitrogen-containing heterocyclic group present in R², R³, R⁴ or R⁵ with a suitable oxidizing agent, such as peroxo carboxylic acids or other peroxides. The person skilled in the art knows if and in which positions compounds of the present invention may form N-oxides.

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 diastere- omers, 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 addi- tion 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 am- monium in which one to four of the hydrogen atoms are replaced by Ci-C₄-alkyl, Ci-C₄- hydroxyalkyl, Ci-C₄-alkoxy, Ci-C₄-alkoxy-Ci-C₄-alkyl, hydroxy-Ci-C₄-alkoxy-Ci-C₄-alkyl, phenyl or benzyl. Examples of substituted ammonium ions comprise methylammonium, isoprop- ylammonium, 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(Ci-C₄- alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-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 Ci-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 "undesired vegetation" ("weeds") is understood to include any vegetation grow- ing 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 C_n- 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 haloalkyi.

The term "alkyl" as used herein (and in the alkyl moieties of other groups comprising an alkyl group, e.g. alkoxy, alkylamino, alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulfonyl and alkoxyalkyi) denotes in each case a straight-chain or branched alkyl group having usually from 1 to 10 carbon atoms, generally from 1 to 8 carbon atoms, frequently from 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms and in particular from 1 to 3 carbon atoms. Examples of Ci-C₄- alkyl are methyl, ethyl, n-propyl, iso-propyl, n-butyl, 2-butyl (sec-butyl), isobutyl and tert-butyl. Examples for Ci-C6-alkyl are, apart those mentioned for Ci-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 Ci-Cs-alkyl are, apart those mentioned for Ci-C6-alkyl, n-heptyl, 1 -methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5- methylhexyl, 1 -ethyl pentyl, 2-ethylpentyl, 3-ethylpentyl, n-octyl, 1 -methylheptyl, 2-methylheptyl, 1 -ethylhexyl, 2-ethylhexyl, 1 ,2-dimethylhexyl, 1 -propylpentyl and 2-propylpentyl. Examples for Ci-Cio-alkyl are, apart those mentioned for Ci-Cs-alkyl, nonyl, decyl, 2-propylheptyl and 3- propylheptyl.

The term "alkylene" (or alkanediyl) as used herein in each case denotes an alkyl radical as defined above, wherein one hydrogen atom at any position of the carbon backbone is replaced by one further binding site, thus forming a bivalent moiety. Ci-C2-Alkylene or C1-C2- alkanediyl is a linear or branched divalent alkyl radical having 1 or 2 carbon atoms. Examples are -CH2-, -CH2CH2- and -CH(CH3)-. Ci-C3-Alkylene or Ci-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-. Ci-C₄-Alkylene or Ci-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-.

The term "haloalkyi" as used herein (and in the haloalkyi moieties of other groups comprising a haloalkyi group, e.g. haloalkoxy, haloalkylthio, haloalkylcarbonyl, haloalkylsulfonyl and haloalkylsulfinyl) denotes in each case a straight-chain or branched alkyl group having usually from 1 to 8 carbon atoms ("Ci-Cs-haloalkyl"), frequently from 1 to 6 carbon atoms ("C1-C6- haloalkyl"), more frequently 1 to 4 carbon atoms ("Ci-C4-haloalkyl"), wherein the hydrogen atoms of this group are partially or totally replaced with halogen atoms. Preferred haloalkyl moie- ties are selected from Ci-C4-haloalkyl, more preferably from Ci-C2-haloalkyl, more preferably from halomethyl, in particular from Ci-C2-fluoroalkyl. 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 Ci-C2-fluoroalkyl are fluo- romethyl, difluoromethyl, trifluoromethyl, 1 -fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2- trifluoroethyl, pentafluoroethyl, and the like. Examples for Ci-C2-haloalkyl are, apart those mentioned for Ci-C2-fluoroalkyl, 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 Ci-C4-haloalkyl are, apart those mentioned for Ci-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 ("Ci-C4-cyanoalkyl") or 1 to 6 ("Ci-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 "cycloalkyi" as used herein (and in the cycloalkyi moieties of other groups comprising a cycloalkyi group, e.g. cycloalkoxy and cycloalkylalkyi) denotes in each case a mono- or bicyclic cycloaliphatic radical having usually from 3 to 10 carbon atoms ("C3-Cio-cycloalkyl"), preferably 3 to 7 carbon atoms ("C3-C7-cycloalkyl") or in particular 3 to 6 carbon atoms ("C3-C6- cycloalkyl"). Examples of monocyclic radicals having 3 to 6 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Examples of monocyclic radicals having 3 to 7 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl. Examples of bicyclic radicals having 7 or 8 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 cycloalkyi denotes a monocyclic saturated hydrocarbon radical.

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 (or inversely expressed, it denotes an alkyl group, as described above, in which one hydrogen atom is replaced by a cycloalkyl group, as defined above). The term "C3-C7-cycloalkyl-Ci-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. Examples are cyclopropylmethyl, cyclopropylethyl, cyclo- propylpropyl, cyclobutylmethyl, cyclobutylethyl, cyclobutylpropyl, cyclopentyl methyl, cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl, cyclohexylpropyl, cycloheptylme- thyl, cycloheptylethyl, cycloheptylpropyl and the like. The term "C3-C6-cycloalkyl-Ci-C6-alkyl" refers to a C3-C6-cycloalkyl group as defined above (preferably a monocyclic cycloalkyl group) which is bound to the remainder of the molecule via a Ci-C6-alkyl group, as defined above. Ex- amples are cyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl, cyclobutylpropyl, cyclopentyl methyl, cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl, cyclohexylpropyl and the like.

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, cyclooct-1 -en-1 -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, cy- clopenta-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 cy- clohexa-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.

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 chlorovinyl, 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 hav- ing usually 3 to 8 carbon atoms ("Cs-Cs-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 ("d-Cs-alkoxy"), frequently from 1 to 6 carbon atoms ("Ci-C6-alkoxy"), preferably 1 to 4 carbon atoms ("Ci-C4-alkoxy"), which is bound to the remainder of the molecule via an oxygen atom. Ci-C2-Alkoxy is methoxy or ethoxy. C1-C4- Alkoxy is additionally, for example, n-propoxy, 1 -methylethoxy (isopropoxy), butoxy,

1 -methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy) or 1 ,1 -dimethylethoxy (tert-butoxy). Ci-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. Ci-Cs-Alkoxy is addition- ally, 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 ("Ci-Cs-haloalkoxy"), frequently from 1 to 6 carbon atoms ("Ci-C6-haloalkoxy"), preferably 1 to 4 carbon atoms ("C1-C4- haloalkoxy"), more preferably 1 to 3 carbon atoms ("Ci-C3-haloalkoxy"), wherein the hydrogen atoms of this group are partially or totally replaced with halogen atoms, in particular fluorine atoms. Ci-C₂-Haloalkoxy is, for example, OCH₂F, OCHF₂, OCF₃, OCH₂CI, OCHC , OCCI₃, 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. Ci-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 -(CH₂CI)-2-chloroethoxy, 1 -(CH₂Br)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy. Ci-C6-Haloalkoxy is addi- tionally, 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 de- fined above, attached via an oxygen atom to the remainder of the molecule. C2-Cs-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 de- fined above, attached via an oxygen atom to the remainder of the molecule. C2-Cs-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-Cs-haloalkynyl group, as defined above, attached via an oxygen atom to the remainder of the molecule. Cs-Cs-Haloalkynyloxy is a Cs-Cs-haloalkynyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.

The term "alkoxyalkyl" 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 radi- cal usually comprising 1 to 8, frequently 1 to 6, in particular 1 to 4, carbon atoms as defined above. The term "Ci-C4-alkoxy-Ci-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 Ci-C4-alkoxy group, as defined above. "Ci-C6-alkoxy-Ci-C6-alkyl" is a C1-C6- alkyl group, as defined above, in which one hydrogen atom is replaced by a Ci-C6-alkoxy group, as defined above. Examples are CH₂OCH₃, CH2-OC2H5, n-propoxymethyl, CH2-OCH(CH₃)2, n- butoxymethyl, (l -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 "Ci- C4-alkoxy-Ci-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 Ci-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. Ci-C4-Haloalkoxy-Ci-C4-alkoxy is a Ci-C4-alkoxy group, wherein one of the hydrogen atoms is replaced by a Ci-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 (CH F2OCH2), 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 cycloalkyi group, as defined above, bound to the remainder of the molecule via an oxygen atom. Examples of C3-C7-cycloalkoxy comprise cyclopropoxy, cy- clobutoxy, cyclopentoxy, cyclohexoxy and cycloheptoxy. Examples of C3-Cio-cycloalkoxy com- prise cyclopropoxy, cyclobutoxy, cyclopentoxy, cyclohexoxy, cycloheptoxy, cyclooctoxy, cy- clononoxy 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 cycloalkyi group, as defined above. The term "C3- Cio-cycloalkyl-Ci-C2-alkoxy" as used herein, refers to an alkoxy group having 1 or 2 carbon at- oms, as defined above, where one hydrogen atom is replaced by a C3-Cio-cycloalkyl group, as defined above. Examples are cyclpropylmethoxy, cyclopropylethoxy, cyclobutylmethoxy, cyclo- butylethoxy, cyclopentylmethoxy, cyclopentylethoxy, cyclohexylmethoxy, cyclohexylethoxy, cy- cloheptylmethoxy, 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 cycloalkyi group, as defined above. The term "C3-C6-cycloalkyl-Ci-C6-alkoxy-Ci-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 Ci- 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(0)_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 ("Ci-Cs-alkylthio"), frequently comprising 1 to 6 carbon atoms ("Ci-C6-alkylthio"), preferably 1 to 4 carbon atoms ("Ci-C4-alkylthio"), which is attached via a sulfur atom at any position in the alkyl group. Ci-C2-Alkylthio is methylthio or ethylthio. Ci-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). Ci-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. Ci-Cs-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. Ci-C₂-Haloalkylthio is, for example, SCH₂F, SCHF₂, SCF₃, SCH₂CI, SCHCI₂, SCC , 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. Ci-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 -(CH₂CI)-2-chloroethylthio, 1 -(CH₂Br)-2-bromoethylthio,

4- fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio or nonafluorobutylthio. Ci-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(0)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 "Ci-C₂-alkylsulfinyl" refers to a Ci-C₂-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term "Ci-C4-alkylsulfinyl" refers to a Ci-C4-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term "Ci-C6-alkylsulfinyl" refers to a Ci-C6-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. Ci-C₂-alkylsulfinyl is methylsulfinyl or ethylsulfinyl. Ci-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(0)k" (wherein k is 2) are equivalent and, as used herein, denote an alkyl group, as defined above, attached via a sulfonyl [S(0)2] group. The term "Ci-C2-alkylsulfonyl" refers to a Ci-C2-alkyl group, as defined above, attached via a sulfonyl [S(0)2] group. The term "Ci-C4-alkylsulfonyl" refers to a Ci-C4-alkyl group, as defined above, attached via a sulfonyl [S(0)2] group. The term "Ci-C6-alkylsulfonyl" refers to a Ci-C6-alkyl group, as defined above, attached via a sulfonyl [S(0)2] group. Ci-C2-alkylsulfonyl is methyl- sulfonyl or ethylsulfonyl. Ci-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). Ci-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 "Ci-C4-alkylthio-Ci-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 Ci-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 "Ci-C4-alkylthio-Ci-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 Ci-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("Ci-C4-alkylamino") or 1 to 3 carbon atoms ("C1-C3- alkylamino"). Examples for Ci-C3-alkylamino are methylamino, ethylamino, n-propylamino and isopropylamino. Examples of Ci-C4-alkylamino are methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, 2-butylamino, iso-butylamino and tert-butylamino.

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

The term "alkylamino-alkyl" denotes an alkyl group, as defined above, wherein one hydro- gen atom is replaced by an alkylamino group, as defined above. Ci-C4-alkylamino-Ci-C4-alkyl is a Ci-C4-alkyl group, as defined above, wherein one hydrogen atom is replaced by a C1-C4- alkylamino group, as defined above. Examples are methylaminomethyl, 1 -(methylamino)-ethyl,

2- (methylamino)-ethyl, 1 -(methylamino)-propyl, 2-(methylamino)-propyl, 3-(methylamino)-propyl, 1 -(methylamino)-prop-2-yl, 2-(methylamino)-prop-2-yl, 1 -(methylamino)-butyl, 2-(methylamino)- butyl, 3-(methylamino)-butyl, 4-(methylamino)-butyl, ethylaminomethyl, 1 -(ethylamino)-ethyl, 2- (ethylamino)-ethyl, 1 -(ethylamino)-propyl, 2-(ethylamino)-propyl, 3-(ethylamino)-propyl, 1 - (ethylamino)-prop-2-yl, 2-(ethylamino)-prop-2-yl, 1-(ethylamino)-butyl, 2-(ethylamino)-butyl, 3- (ethylamino)-butyl, 4-(ethylamino)-butyl, propylaminomethyl, 1 -(propylamino)-ethyl, 2- (propylamino)-ethyl, 1 -(propylamino)-propyl, 2-(propylamino)-propyl, 3-(propylamino)-propyl, 1 - (propylamino)-prop-2-yl, 2-(propylamino)-prop-2-yl, 1 -(propylamino)-butyl, 2-(propylamino)-butyl,

3- (propylamino)-butyl, 4-(propylamino)-butyl, butylaminomethyl, 1 -(butylamino)-ethyl, 2- (butylamino)-ethyl, 1 -(butylamino)-propyl, 2-(butylamino)-propyl, 3-(butylamino)-propyl, 1 - (butylamino)-prop-2-yl, 2-(butylamino)-prop-2-yl, 1-(butylamino)-butyl, 2-(butylamino)-butyl, 3- (butylamino)-butyl, 4-(butylamino)-butyl and the like.

The term "dialkylamino-alkyl" denotes an alkyl group, as defined above, wherein one hy- drogen atom is replaced by a dialkylamino group, as defined above. Di-(Ci-C₄-alkyl)-amino-Ci- C₄-alkyl is a Ci-C₄-alkyl group, as defined above, wherein one hydrogen atom is replaced by a di-(Ci-C₄-alkyl)-amino group, as defined above. Examples are dimethylaminomethyl, 1 - (dimethylamino)-ethyl, 2-(dimethylamino)-ethyl, 1 -(dimethylamino)-propyl, 2-(dimethylamino)- propyl, 3-(dimethylamino)-propyl, 1 -(dimethylamino)-butyl, 2-(dimethylamino)-butyl, 3- (dimethylamino)-butyl, 4-(dimethylamino)-butyl, (ethylmethylamino)-methyl, 1 -

(ethylmethylamino)-ethyl, 2-(ethylmethylamino)-ethyl, 1 -(ethylmethylamino)-propyl, 2- (ethylmethylamino)-propyl, 3-(ethylmethylamino)-propyl, 1 -(ethylmethylamino)-butyl, 2- (ethylmethylamino)-butyl, 3-(ethylmethylamino)-butyl, 4-(ethylmethylamino)-butyl, (diethyla- mino)-methyl,1 -(diethylamino)-ethyl, 2-(diethylamino)-ethyl, 1 -(diethylamino)-propyl, 2- (diethylamino)-propyl, 3-(diethylamino)-propyl, 1 -(diethylamino)-butyl, 2-(diethylamino)-butyl, 3- (diethylamino)-butyl, 4-(diethylamino)-butyl, (dipropylamino)-methyl,1 -(dipropylamino)-ethyl, 2- (dipropylamino)-ethyl, 1 -(dipropylamino)-propyl, 2-(dipropylamino)-propyl, 3-(dipropylamino)- propyl, 1 -(dipropylamino)-butyl, 2-(dipropylamino)-butyl, 3-(dipropylamino)-butyl, 4- (dipropylamino)-butyl, (dibutylamino)-methyl,1 -(dibutylamino)-ethyl, 2-(dibutylamino)-ethyl, 1 - (dibutylamino)-propyl, 2-(dibutylamino)-propyl, 3-(dibutylamino)-propyl, 1 -(dibutylamino)-butyl, 2- (dibutylamino)-butyl, 3-(dibutylamino)-butyl, 4-(dibutylamino)-butyl and the like.

The substituent "oxo" replaces a Chb group by a C(=0) 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=0 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(=0)] group to the remainder of the molecule. Ci-C3-Alkylcarbonyl is a Ci-C3-alkyl group, as defined above, attached via a carbonyl [C(=0)] group to the remainder of the molecule. C1-C4- Alkylcarbonyl is a Ci-C₄-alkyl group, as defined above, attached via a carbonyl [C(=0)] group to the remainder of the molecule. Examples for Ci-C3-alkylcarbonyl are acetyl (methylcarbonyl), propionyl (ethylcarbonyl), propylcarbonyl and isopropylcarbonyl. Examples for C1-C4- alkylcarbonyl are acetyl (methylcarbonyl), propionyl (ethylcarbonyl), propylcarbonyl, isopropylcarbonyl n-butylcarbonyl and the like.

Ci-C₄-alkyl-C(0)-Ci-C₄-alkyl is a Ci-C₄-alkyl group in which one hydrogen atom is replaced by a Ci-C₄-alkylcarbonyl group.

Ci-C₄-alkyl-0-C(0)-Ci-C₄-alkyl is a Ci-C₄-alkyl group in which one hydrogen atom is replaced by a Ci-C₄-alkoxycarbonyl group. Ci-C2-alkyl-0-C(0)-Ci-C₄-alkyl is a Ci-C₄-alkyl group in which one hydrogen atom is replaced by a Ci-C2-alkoxycarbonyl group. (Ci-C4-alkyl)2N-C(0)-Ci-C4-alkyl is a Ci-C4-alkyl group in which one hydrogen atom is replaced by a di-(Ci-C4-alkyl)-aminocyrbonyl group. (Ci-C2-alkyl)2N-C(0)-Ci-C4-alkyl is a C1-C4- alkyl group in which one hydrogen atom is replaced by a di-(Ci-C2-alkyl)-aminocyrbonyl group.

The term "aryl" as used herein refers to a mono-, bi- or tricyclic aromatic hydrocarbon rad- ical such as phenyl or naphthyl, in particular phenyl.

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, pyrim- idyl and the like.

Heterocyclic rings or heterocyclyl or heteroaromatic rings or heteroaryl or hetaryl contain one or more heteroatoms as ring members, i.e. atoms different from carbon. In the terms of the present invention, these heteroatoms are N, O and S, where N and S can also be present as oxidized heteroatom groups, namely as NO, SO or SO2. Thus, in the terms of the present invention, rings termed as heterocyclic rings or heterocyclyl or heteroaromatic rings or heteroaryl or hetaryl contain one or more heteroatoms and/or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2 as ring members.

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

Unsaturated rings contain at least one C-C and/or C-N and/or N-N double bond(s). Maximally unsaturated rings contain as many conjugated C-C and/or C-N and/or N-N double bonds as allowed by the ring size. 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. Partially unsaturated rings (in terms of the present invention often simply termed just as "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.

The heterocyclic rings or heterocyclyl or heteroaromatic rings or heteroaryl or hetaryl 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 ring contains at least one carbon ring atom. If the ring contains more than one O ring atom, these are not adjacent.

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 oxi- dized to various oxidation states, i.e. as SO or SO2. An aromatic monocyclic heterocycle is a fully unsaturated 5- or 6-membered monocyclic heterocycle. 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, tetrahy- drothien-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, imidazoli- din-4-yl, oxazolidin-2-yl, oxazolidin-3-yl, oxazolidin-4-yl, oxazolidin-5-yl, isoxazolidin-2-yl, isoxa- zolidin-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, pi- perazin-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 tetrahydro- pyridazinyl, 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 tetrahydrotria- zin-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, ben- zimidazolyl, 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 R^2a and R^2b or R^3c and R^3d or R^3e and R^3f or R¾ and R^3h) 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 O, S and N, this is for example azetidin-1 -yl, pyrrolidin-1 -yl, pyrazolidin-1 -yl, imidazolidin-1 -yl, oxazolidin-3-yl, thiazolidin-3-yl, isoxazolidin-2-yl, isothiazolidin-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]-thiad iazolid i n-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, piperazin-1 - yl, morpholin-4-yl, thiomorpholin-4-yl, 1 -oxothiomorpholin-4-yl, 1 ,1 -dioxothiomorpholin-4-yl, aze- pan-1 -yl, 1 ,4-diazepan-1 -yl, pyrrolin-1 -yl, pyrazolin-1 -yl, imidazolin-1 -yl, oxazolin-3-yl, isoxa- zolin-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]-1 H-triazol-1 -yl, [1 ,2,3]-2H-triazol-2-yl, [1 ,2,4]-1 H-triazol-1 -yl and [1 ,2,4]-4H-triazol-4-yl.

Two radicals bound on the same nitrogen atom (such as R^2a and R^2b), together with the nitrogen atom to which they are bound, may form a 6-, 7-, 8-, 9- or 10-membered, saturated or partially unsaturated heterobicyclic radical , where the heterobicyclic radical may contain as a ring member a further heteroatom selected from O, S and N. Such a heterobicyclic ring is of course N-bound. Heterobicyclic rings contain two rings which have at least one ring atom in common. In the present case, one of the two rings contains a nitrogen ring atom via which this ring is attached to the remainder of the molecule. This same ring or the other ring may contain a further heteroatom selected from the group consisting of N, O and S as ring member. The het- erobicyclic radical may be a condensed (fused) ring system, in which the two rings have two neighboring ring atoms in common, a spiro system, in which the rings have only one ring atom in common, or a bridged system with at least three ring atoms in common. Preferably, the heterobicyclic ring is 7-, 8-, 9- or 10-membered and is preferably saturated.

Examples for fused N-bound 7-, 8-, 9- or 10-membered saturated heterobicyclic rings which may contain as a ring member a further heteroatom selected from O, S and N are:

and the like.

Examples for spiro-bound N-bound 7-, 8-, 9- or 10-membered heterobicyclic rings which may contain as a ring member a further heteroatom selected from O, S and N are:

and the like.

Examples for bridged N-bound 7-, 8-, 9- or 10-membered heterobicyclic rings which may contain as a ring member a further heteroatom selected from O, S and Nare:

and the like.

In the above structures # denotes the attachment point to the remainder of the molecule.

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 or a stereoisomer, or an N-oxide or salt thereof, wherein the salt is an agriculturally suitable salt. Particularly preferred compounds according to the invention are compounds of formula I, an N-oxide or a salt thereof, especially an agriculturally suitable salt thereof.

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

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, R², R³, R⁴, R⁵ and R^6a are as defined herei

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

(Q²), 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, R², R³, R⁴, R⁵ and R^6b are as defined herein:

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

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, R², R³, R⁴ and R⁶ are as defined herein:

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

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, R², R³, R⁴ and R⁶ are as defined herein:

(I.D) 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.

Particularly, however, the compounds I are a compound I.A.

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, R², R³, R⁴, R⁵ and R^6a, R^6b, R^6c or R^6d 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.

Preferred compounds according to the invention are compounds of formula I, wherein R¹ is selected from the group consisting of cyano, halogen, nitro, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci- C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, Ci-C6-alkoxy, Ci-C4-alkoxy-Ci-C4-alkoxy- Z¹, R^1b-S(0)k-Z¹, where k and Z¹ are as defined herein and where R^1b is as defined above and in particular selected from the group consisting of Ci-C4-alkyl and Ci-C4-haloalkyl. In this context Z¹ is in particular a covalent bond.

More preferably, R¹ is selected from halogen, nitro, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkoxy-Z¹ and R^1b-S(0)_k-Z¹, where k and Z¹ are as defined herein and where R^1b is as defined above and in particular selected from the group consisting of Ci-C4-alkyl and Ci-C4-haloalkyl. In this context Z¹ is in particular a covalent bond.

In particular, R¹ is selected from the group consisting of halogen, nitro, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy-Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio, Ci-C4-haloalkylthio and C1-C4- alkylsulfonyl. More particularly, R¹ is selected from the group consisting of halogen and C1-C4- alkyl.

Specifically R¹ is F, CI, Br, I, nitro, CH₃, CF₃, SCH₃, SCF₃, S0₂CH₃ or CH₂OCH₂CH₂OCH₃, more specifically R¹ is F, CI, Br, I, nitro, CH₃, CF₃, SCH₃ or S0₂CH₃, even more specifically R¹ is CI, Br, CH₃ or CF₃, especially R¹ is CI, Br or CH₃ and very especially R¹ is CI or CH₃. Particularly specifically, R¹ is CI.

According to particular groups 1 a, 2a, 3a and 4a of embodiments of the invention the vari- able R² in the compounds of formula I and likewise in compounds of the formulae I.A, I.B, I.C and I.D is a radical of the formula 2a:

where # in formula 2a indicates the point of attachment to the oxygen atom bearing R² and where the variables Z², R^2a and R^2b are as defined herein or have the preferred meanings given below. These groups of embodiments are herein called embodiment A or embodiments 1 a, 2a, 3a and 4a, which means that group 1 a of embodiments is the subset of group 1 of embodiments, where R² is a radical of the formula 2a, group 2a of embodiments is the subset of group 2 of embodiments, where R² is a radical of the formula 2a, group 3a of embodiments is the subset of group 3 of embodiments, where R² is a radical of the formula 2a and group 4a of embodiments is the subset of group 4 of embodiments, where R² is a radicalof the formula 2a.

Particular preference is given to group 1 a of embodiments. Preference is also given to group 2a of embodiments.

Preferably, Z² is a covalent bond or a bivalent radical selected from Ci-C4-alkanediyl and Ci-C4-alkanediyl-0-Ci-C4-alkanediyl, where in the last two mentioned radicals the C1-C4- alkanediyl groups are linear and unsubstituted, or partly or completely fluorinated or substituted by 1 , 2, 3 or 4 groups selected from Ci-C4-alkyl.

More preferably, Z² is a bond, linear Ci-C3-alkandiyl, which is unsubstituted or partly or completely fluorinated or substituted by 1 , 2, 3 or 4 groups selected from Ci-C3-alkyl.

Even more preferably, Z² is selected from a bond and linear Ci-C3-alkandiyl, which is unsubstituted or partly or completely fluorinated or which carries 1 , 2, 3 or 4 methyl groups; and in particular Z² is a bond, CH₂, CH(CH₃), C(CH₃)₂ or CF₂. Specifically, Z² is a bond, CH₂ or CH(CH₃).

Preferably, R^2a is selected from the group consisting of hydrogen, Ci-C6-alkyl, C1-C6- haloalkyl, C3-C7-cycloalkyl, Ci-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 heteroa- toms 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, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.

More preferably, R^2a is selected from the group consisting of hydrogen, Ci-C6-alkyl, C1-C6- haloalkyl, C3-C6-cycloalkyl, benzyl and heterocyclylmethyl, where heterocyclyl in the last mentioned radical is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic, preferably aromatic, heterocycle, which contains 1 , 2 or 3 heteroatoms as ring members, which are selected from the group consisting of O and N, where benzyl 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, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy.

Even more preferably, R^2a is hydrogen, Ci-C4-alkyl, Ci-C3-haloalkyl, C3-C6-cycloalkyl, benzyl or heterocyclylmethyl, where heterocyclyl in the last mentioned radical is a 5- or 6-membered monocyclic partially unsaturated or aromatic, preferably aromatic, heterocycle, which contains 1 or 2 heteroatoms as ring members, which are selected from the group consisting of O and N.

In particular, R^2a is hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, or heterocyclylmethyl, where heterocyclyl in the last mentioned radical is a 5- or 6-membered monocyclic partially unsaturated or aromatic, preferably aromatic, heterocycle, which contains 1 or 2 nitrogen atoms as ring members; especially R^2a is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, CH₂CF3, cyclopropyl or 1 -pyrazolyl-methyl, and specifically hydrogen, methyl, ethyl, n-propyl, isopropyl, CH₂CF3, or cyclopropyl. Preferably, R^2b is selected from the group consisting of hydrogen, Ci-C6-alkyl, C1-C6- haloalkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-methyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, d-Ce-alkoxy, Ci-C₄-alkoxy-Ci-C₄-alkyl, Ci-C₄-alkoxy-Ci-C -alkoxy, Ci-C -alkyl-S(0)_n-Ci-C - alkyl, Ci-C -alkyl-C(0)-Ci-C -alkyl, Ci-C -alkyl-0-C(0)-Ci-C -alkyl, (Ci-C -alkyl)₂N-C(0)-Ci-C - alkyl, 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, 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, Ci-C₄-alkyl, Ci-C₄-haloalkyl, Ci-C₄- alkoxy and Ci-C₄-haloalkoxy.

More preferably R^2b is selected from the group consisting of hydrogen, Ci-C6-alkyl, C1-C3- haloalkyl, C₃-C₆-cycloalkyl, Ci-C -alkoxy, Ci-C₂-alkyl-0-C(0)-Ci-C -alkyl, (Ci-C₂-alkyl)₂N-C(0)- Ci-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, Ci-C₄-alkyl and Ci-C₄-alkoxy,

Even more preferably R^2b is selected from the group consisting of hydrogen, Ci-C6-alkyl, d-Cs-haloalkyl, C₃-C₆-cycloalkyl, Ci-C₃-alkoxy, Ci-C₂-alkyl-0-C(0)-Ci-C -alkyl, (Ci-C₂-alkyl)₂N- C(0)-Ci-C₄-alkyl, phenyl, which is unsubstituted or substituted by 1 or 2 groups, which are iden- tical or different and selected from the group consisting of methyl, ethyl, methoxy, CI and F; and benzyl; in particular R^2b is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert- butyl, CH₂-C(CH₃)₃, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, CH₂CHCICH₃, cyclopropyl, cyclopentyl, cyclohexyl, methoxy, 1 -methyl-1 -(methoxycarbonyl)ethyl, N,N-dimethylaminocarbonylmethyl, phenyl which is unsubstituted or substituted by 1 or 2 groups selected from methyl, methoxy, CI and F; or benzyl; and specifically R^2b is hydrogen, methyl, ethyl, tert. -butyl, 2,2,2-trifluoroethyl, methoxy, 1 -methyl-1 -(methoxycarbonyl)ethyl or phenyl which is unsubstituted or substituted by 1 or 2 groups selected from methyl, CI and F. Very specifically, R^2b is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert. -butyl, CH₂-C(CH₃)₃, cyclopropyl or phenyl which is unsubstituted or substituted by 1 or 2 CI atoms.

Alternatively, it is also preferred that R^2a, R^2b together with the nitrogen atom, to which they are bound form a 5-, 6-, 7- or 8-membered, saturated heteromonocyclic radical or form a saturated 7-, 8-, 9- or 10-membered heterobicydic radical, where the heteromonocyclic or heterobicycic radical may contain as a ring member a further heteroatom selected from O, S and N and where the heterocyclic radical is unsubstituted or carries 1 , 2, 3 or 4 groups R^2e or carries 1 group R²* and 0, 1 , 2 or 3 groups R^2e, where

R^2e is selected from the group consisting of halogen and Ci-C₄-alkyl, and

R^2f is selected from R^4c-C(0)-, R^4dO-C(0)- and R^4eR^4fN-C(0)-, where R^4c, R^4d, R^4e and R^4f, independently of each other are Ci-C₄-alkyl or Ci-C₄-haloalkyl.

In this context it is more preferred that R^2a, R^2b together with the nitrogen atom to which they are bound form a 5-, 6- or 7-membered saturated heteromonocyclic radical or form a 7-, 8-, 9- or 10-membered saturated heterobicydic radical, where the heterobicycic radical is a fused or a bridged ring system, where the heteromonocyclic or heterobicycic radical may contain as a ring member a further heteroatom selected from O and N and where the heteromonocyclic or heterobicycic radical is unsubstituted or carries 1 , 2, 3 or 4 groups R^2e or carries 1 group R^2f and 0, 1 , 2 or 3 groups R^2e, where

R^2e is Ci-C₄-alkyl; and

R^2f is selected from R^4c-C(0)-, R^4dO-C(0)- and R^4eR^4fN-C(0)-, where R^4c, R^4d, R^4e and R^4f, independently of each other are Ci-C₄-alkyl or Ci-C₄-haloalkyl; in particular Ci-C₄-alkyl.

In case that R^2a, R^2b together with the nitrogen atom to which they are bound form a 5-, 6- or 7-membered, saturated heteromonocyclic radical, preferably this may contain as a ring member a further heteroatom selected from O and N and where the heteromonocyclic or heterobicy- clic radical is unsubstituted or carries 1 , 2 or 3 groups R^2e or carries 1 group R^2f and 0, 1 or 2 groups R^2e, where

R^2e is methyl or ethyl; and

R^2f is selected from R^4c-C(0)-, R^4dO-C(0)- and R^4eR^4fN-C(0)-, where R^4c, R^4d, R^4e and R^4f, independently of each other are Ci-C2-alkyl.

In this context, if R^2a, R^2b together with the nitrogen atom, to which they are bound form a saturated heteromonocyclic radical, it is even more preferred that this is selected from morpho- lin-4-yl, pyrrolidin-1 -yl, piperidin-1 -yl, piperazin-1 -yl and 1 ,4-oxazepan-4-yl; in particular from morpholin-4-yl, pyrrolidin-1 -yl, piperidin-1 -yl and piperazin-1 -yl, where the aforementioned heterocyclic radicals are unsubstituted or carry 1 , 2 or 3 groups R^2e or carry 1 group R^2f and 0, 1 or 2 groups R^2e, where

R^2e is methyl or ethyl; and

R^2f is selected from CH₃-C(0)-, CH₃0-C(0)- and (CH₃)₂N-C(0)-.

In this context, if R^2a, R^2b together with the nitrogen atom, to which they are bound form a saturated heterobicyclic radical, this is preferably a 7- or 8-membered saturated bridged ring system which may contain as a ring member a further heteroatom selected from O and N, or is a 10-membered fused ring system which may contain as a ring member a further heteroatom selected from O and N. Specifically, this heterobocyclic ring is selected from 6-oxa-3- azabicyclo[3.1.1 ]heptan-3-yl, 8-oxa-3-azabicyclo[3.2.1 ]octan-3-yl and 3,4,4a, 5,6,7,8, 8a- octahydro-2H-benzo[b][1 ,4]oxazin-4-yl.

According to embodiment A of the invention it is particularly preferred that the moiety NR^2aR^2b of the formula 2a is a radical selected from the group consisting of Nhb, methylamino, ethylamino, n-propylamino, isopropylamino, tert.-butylamino, 2,2-dimethylprop-1 -ylamino, dime- thylamino, diethylamino, di-(n-butyl)-amino, 2,2,2-trifluoroethylamino, 2,2-difluoroethylamino, N- cyclopropylamino, N-cyclopentylamino, N-cyclohexylamino, N-methyl-N-ethylamino, N-methyl- N-isopropylamino, N-methoxy-N-methylamino, N-methyl-N-2,2-dimethylprop-1 -ylamino, N- methyl-N-(2,2,2-trifluoroethyl)amino, N-methyl-N-(2,2-difluoroethyl)amino, N-ethyl-N-(2,2,2- trifluoroethyl)amino, N-propyl-N-(2,2,2-trifluoroethyl)amino, N-isopropyl-N-(2,2,2- trifluoroethyl)amino, N-isobutyl-N-(2,2,2-trifluoroethyl)amino, N-isopropyl-N-(2-chloro-1 -propyl- amino, N-(N,N-dimethylaminocarbonylmethyl)-N-(2,2,2-trifluoroethyl)amino, N-methyl-N- cyclopropylamino, N-ethyl-N-cyclopropylamino, dicyclopropylamino, N-(1 -methyl-1 - (methoxycarbonyl)ethyl)amino, N-phenylamino, N-methyl-N-phenylamino, N-methyl-N-(4- chlorophenyl)amino, N-methyl-N-(4-fluorophenyl)amino, N-methyl-N-(4-methoxyphenyl)amino, N-benzyl-N-(2,2,2-trifluoroethyl)amino, N-(4-chlorophenyl)-N-(2,2,2-trifluoroethyl)amino, N-ethyl- N-isopropylamino, N-ethyl-N-(2,2,2-trifluoroethyl)amino, N-ethyl-N-(2,2-difluoroethyl)amino, N- ethyl-N-phenylamino, N-ethyl-N-cyclopropylamino, Ν,Ν-diisopropylamino, N-isopropyl-N- cyclopropyl-amino, N-isopropyl-N-(2,2,2-trifluoroethyl)amino, N-isopropyl-N-(2,2- difluoroethyl)amino, N-isopropyl-N-phenylamino, Ν,Ν-dicyclopropylamino, N-cyclopropyl-N- (2,2,2-trifluoroethyl)amino, N-cyclopropyl-N-(2,2-difluoroethyl)amino, N,N-di-(2,2,2- trifluoroethyl)amino, N,N-di-(2,2-difluoroethyl)amino, N-(2,2,2-trifluoroethyl)-N-(2,2- difluoroethyl)amino, N-methoxy-N-(2,2-difluoroethyl)amino, N-methoxy-N-(2,2,2- trifluoroethyl)amino, N-methoxy-N-isopropylamino, N-methoxy-N-cyclopropylamino, N- cyclopropyl-N-phenylamino, N-(2,2,2-trifluoroethyl)-N-phenylamino, N-(2,2-difluoroethyl)-N- phenylamino, N-ethyl-N-(4-chlorophenyl)amino, N-cyclopropyl-N-(4-chlorophenyl)amino, N- isopropyl-N-(4-chlorophenyl)amino, N-(2,2,2-trifluoroethyl)-N-(4-chlorophenyl)amino, N-(2,2- difluoroethyl)-N-(4-chlorophenyl)amino, N-methyl-N-(4-methoxyphenyl)amino, N-ethyl-N-(4- methoxyphenyl)amino, N-isopropyl-N-(4-methoxyphenyl)amino, N-cyclopropyl-N-(4- methoxyphenyl)amino, N-(2,2,2-trifluoroethyl)-N-(4-methoxyphenyl)amino, N-(2,2-difluoroethyl)- N-(4-methoxyphenyl)amino, N-(2,6-dimethylphenyl)-N-((1 -imidazolyl)methyl)amino,

morpholin-4-yl, 2-methylmorpholin-4-yl, 3-methylmorpholin-4-yl, 2-ethylmorpholin-4-yl, 2,2- dimethylmorpholin-4-yl, 3,3-dimethylmorpholin-4-yl, 2,3-dimethylmorpholin-4-yl, 2,5- dimethylmorpholin-4-yl, 2,6-dimethylmorpholin-4-yl, 3,5-dimethylmorpholin-4-yl, 2,6,6- trimethylmorpholin-4-yl, 2,5-diethylmorpholin-4-yl, 2,6-diethylmorpholin-4-yl, pyrrolidin-1 -yl, pi- peridin-1 -yl, piperazin-1 -yl, 4-methoxycarbonylpiperazin-1 -yl, 4-(N,N- dimethylaminocarbonyl)piperazin-1 -yl, 4-(methylcarbonyl)piperazin-1 -yl, 7-methyl-1 ,4-oxazepan- 4-yl, 6-oxa-3-azabicyclo[3.1.1 ]heptan-3-yl, 8-oxa-3-azabicyclo[3.2.1]octan-3-yl and

3,4,4a, 5,6,7,8,8a-octahydro-2H-benzo[b][1 ,4]oxazin-4-yl.

According to other particular groups 1 b, 2b, 3b and 4b of embodiments of the invention the variable R² in the compounds of formula I and likewise in compounds of the formulae I .A, I.B, I.C and I.D is a radical of the formula 2b:

where # in formula 2b indicates the point of attachment to the oxygen atom bearing R² and where the variables Z, R^2c, R^2d and p are as defined herein or have the preferred meanings given below. These groups of embodiments are herein called embodiment B or embodiments 1 b, 2b, 3b and 4b, which means that group 1 b of embodiments is the subset of group 1 of embodiments, where R² is a radical of the formula 2b, group 2b of embodiments is the subset of group 2 of embodiments, where R² is a radicalof the formula 2b, group 3b of embodiments is the sub- set of group 3 of embodiments, where R² is a radical of the formula 2b and group 4b of embodiments is the subset of group 4 of embodiments, where R² is a radicalof the formula 2b. Particular preference is given to group 1 b of embodiments. Preference is also given to group 2b of embodiments.

Preferably, Z is a covalent bond or linear Ci-C₃-alkanediyl; more preferably Z is CH₂, CH2CH2 or CH2CH2CH2; and in particular Z is CH₂ or CH₂CH₂.

Preferably R^2c is selected from the group consisting of hydrogen, Ci-C4-alkyl, C1-C3- haloalkyl, C3-C6-cycloalkyl, Ci-C3-alkoxyphenyl, which is unsubstituted or substituted by 1 or 2 groups, which are identical or different and selected from the group consisting of methyl, ethyl, CI and F.

More preferably R^2c is selected from the group consisting of hydrogen, Ci-C6-alkyl and Ci- C6-haloalkyl, and in particular R^2c is hydrogen, methyl, ethyl, CF2 or CH2CF3.

Preferably p is 0, 1 or 2; more preferably p is 0 or 1 ; and in particular p is 0.

Preferably R^2d is selected from the group consisting of halogen and Ci-C4-alkyl, more preferably R^2d is methyl, ethyl, chlorine or fluorine; and in particular R^2d is methyl or fluorine.

According to embodiment B of the invention it is particularly preferred that the moiety of the formula 2b is a radical selected from the group consisting of pyrrolidin-2-on-3-yl, 1 - methylpyrrolidin-2-on-3-yl, 1 -(2,2,2-trifluoroethyl)pyrrolidin-2-on-3-yl, piperidin-2-on-3-yl, 1 - methylpiperidin-2-on-3-yl and azepan-2-on-3-yl.

Preferred compounds according to the invention are compounds of formula I, wherein R³ is selected from the group consisting of hydrogen, cyano, halogen, nitro, Ci-C6-alkyl, C-i-Cs- haloalkyl, Ci-C4-alkoxy, d-Cs-haloalkoxy-Z³, C2-C4-alkenyl, C2-C4-alkynyl, C2-C4-alkenyloxy, C2- C4-alkynyloxy and R^3b-S(0)k-Z³, where the variables k, R^3b and Z³ have one of the herein defined meanings; more preferably, R³ is selected from the group consisting of halogen, nitro, Ci- Ce-alkyl, Ci-Ce-haloalkyl, Ci-C₈-haloalkoxy-Z³, and R^3b-S(0)_k-Z³, where the variables k, R^3b and Z³ have one of the herein defined meanings; even more preferably, R³ is selected from the group consisting of halogen, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-haloalkoxy, and R^3b-S(0)k, where the variables k and R^3b have one of the herein defined meanings.

In particular, R³ is selected from the group consisting of halogen, nitro, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C₄-haloalkoxy, Ci-C₄-alkylthio, Ci-C₄-haloalkylthio, Ci-C₄-alkyl-S(0), C1-C4- haloalkyl-S(O), Ci-C₄-alkyl-S(0)₂, and Ci-C₄-haloalkyl-S(0)₂. More particularly, R³ is selected from the group consisting of halogen, Ci-C4-haloalkyl, Ci-C4-alkylthio and Ci-C4-alkylsulfonyl.

Specifically, R³ is selected from the group consisting of halogen, nitro, Ci-C2-alkyl, C1-C2- haloalkyl, Ci-C₂-haloalkoxy, Ci-C₂-alkylthio, Ci-C₂-haloalkylthio, Ci-C₂-alkyl-S(0), C1-C2- haloalkyl-S(O), Ci-C₂-alkyl-S(0)₂ and Ci-C₂-haloalkyl-S(0)₂, more specifically from CI, F, Br, I, N0₂, CH₃, CF₃, CHF₂, OCF3, OCHF2, SCH₃, SCF₃, SCHF₂, S(0)CH₃, S(0)CH₂CH₃, S(0)₂CH₃ and S(0)2CH₂CH₃, and very specifically R³ is CI, Br, I, CF₃, SCH₃, S(0)CH₃ or S(0)₂CH₃.

In the context of R³, R^3c is preferably selected from the group consisting of Ci-C6-alkyl, C3- C₇-cycloalkyl, C₃-C₇-cycloalkyl-Ci-C4-alkyl, Ci-C₆-haloalkyl, Ci-C₆-alkoxy, 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, Ci-C₄-alkyl, Ci-C₄-haloalkyl, Ci-C₄-alkoxy and Ci-C₄-haloalkoxy;

More preferably, R^3c is selected from the group consisting of CrC₄-alkyl, C₃-C₇-cycloalkyl, d- C₄-haloalkyl, CrC₄-alkoxy, 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 CrC₄-alkoxy;

Herein, particularly preferably, R^3c is methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2-, CF3CH2-, CH3O-, 4-CI-phenyl, 4-CH₃0-phenyl, or phenyl.

In the context of R³, R^3d is preferably selected from the group consisting of Ci-C6-alkyl, C3- C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C₄-alkyl, Ci-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, Ci-C₄-alkyl, Ci-C₄-haloalkyl, Ci-C₄-alkoxy and Ci-C₄-haloalkoxy; more preferably, R^3d is selected from the group consisting of Ci-C₄-alkyl, C3-C7-cycloalkyl, and Ci-C₄-haloalkyl;

Herein, very particularly preferably, R^3d is methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr),

Preferred compounds according to the invention are compounds of formula I, wherein in

R³, Z³ is Ci-C₄-alkanediyl; preferably, Z³ is -CH₂- or -CH₂CH₂-.

According to another preferred embodiment, Z³ is a covalent bond.

Preferred compounds according to the invention are compounds of formula I, wherein R⁴ is selected from the group consisting of hydrogen, cyano, halogen, nitro, Ci-C2-alkyl, and C1-C2- haloalkyl.

More preferably, 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 formula I, wherein R⁴ is hydrogen, chlorine or fluorine.

Most preferred compounds according to the invention are compounds of formula I, wherein R⁴ is hydrogen.

Preferred compounds according to the invention are compounds of formula I, wherein R⁵ is selected from the group consisting of CHF2, CF3 and halogen.

More preferably, R⁵ is halogen, in particular chlorine or fluorine, especially fluorine.

Preferred compounds according to the invention are compounds of formula I, wherein R^6a, R^6b, R^6c, R^6d are, independently of each other, selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C₄-alkoxy-Ci-C₄-alkyl, and phenyl.

In particular, R^6a, R^6b, R^6c, R^6d are, independently of each other, selected from the group consisting of hydrogen, Ci-C3-alkyl, Ci-C2-alkoxy-Ci-C2-alkyl, specifically from H, CH3, CH3CH2, CH3CH2CH2, CH3OCH2CH2 and CH3OCH2, more specifically from H, CH₃, CH3CH2 and

CH3CH2CH2, and are, very specifically and independently of each other, CH3.

In the context of the present invention, the variables R¹¹, R²¹, R²², R²³, R²⁴, R²⁵, Z¹, Z³, Z^3a, R^b, R^1b, R³ , R^3c, R^3d, R^3e, R^3f, R¾, R^3h, R⁴ , R^4c, R^4d, R^4e, R^4f, R⁴9, R^4h, R^k, R^z, n and k, independently of each other, preferably have one of the following meanings: R¹¹, R²¹ independently of each other are selected from halogen, Ci-C4-alkyl, C3-C6- cycloalkyl, C3-C6-halocycloalkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, C1-C4- alkylthio-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy and Ci-C6-haloalkyloxy, more preferably from halogen, Ci-C4-alkyl, C3-C6-cycloalkyl, Ci-C4-haloalkyl and Ci-C4-alkoxy.

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

R²² is selected from hydrogen, Ci-C6-alkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C6- haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C4-alkoxy-Ci- 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, Ci-C4-alkyl, C1-C4- haloalkyl and Ci-C4-alkoxy.

More preferably R²² is selected from hydrogen, Ci-C4-alkyl, Ci-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, R²² is selected from hydrogen, Ci-C4-alkyl, Ci-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.

R²³ is selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C3-C6-cycloalkyl and phenyl.

More preferably R²³ is selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl and C3-C6- cycloalkyl; and in particular, R²³ is selected from hydrogen, Ci-C3-alkyl and Ci-C3-haloalkyl.

R²⁴ is selected from Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C3-C6-cycloalkyl and phenyl.

More preferably R²⁴ is selected from Ci-C4-alkyl, Ci-C4-haloalkyl and C3-C6-cycloalkyl; and in particular R²³ is selected from Ci-C3-alkyl and Ci-C3-haloalkyl.

R²⁵ is selected from Ci-C6-alkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C4-alkoxy-Ci-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, Ci-C4-alkyl, C1-C4- haloalkyl and Ci-C4-alkoxy. More preferably R²⁵ is selected from Ci-C4-alkyl, Ci-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 Ci-C4-alkyl, Ci-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.

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

Z^3a is selected from a covalent bond, Ci-C2-alkanediyl, 0-Ci-C2-alkanediyl, C1-C2- alkanediyl-0 and Ci-C2-alkanediyl-0-Ci-C2-alkanediyl; more preferably from a covalent bond, methanediyl, ethanediyl, O-methanediyI, O-ethanediyI, methanediyl-O, and ethanediyl-O; and in particular from a covalent bond, methanediyl and ethanediyl.

R^b, R^1b, R^3b, R^4b independently of each other are selected from d-Ce-alkyl, C3-C7- cycloalkyl, Ci-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, Ci-C4-alkyl, Ci-C2-haloalkyl and C1-C2- alkoxy.

More preferably R^b, R^1b, R^3b, R^4b independently of each other are selected from the group consisting of Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, Ci-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, R^b, R^1b, R^3b, R^4b independently of each other are selected from Ci-C4-alkyl, Ci-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.

R^3c, R^4c, R^k independently of each other are selected from hydrogen, Ci-C6-alkyl, C3-C7- cycloalkyl, which is unsubstituted or partly or completely halogenated, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C4-alkoxy-Ci-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, Ci-C4-alkyl, Ci-C4-haloalkyl and Ci- C4-alkoxy. More preferably R^3c, R^4c, R^k independently of each other are selected from hydrogen, Ci- C4-alkyl, Ci-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, R^3c, R^4c, R^k independently of each other are selected from hydrogen, C1-C4- alkyl, Ci-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.

R^3d, R^4d independently of each other are selected from Ci-C6-alkyl, C3-C7-cycloalkyl, which is unsubstituted or partly or completely halogenated, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and benzyl.

More preferably R^3d, R^4d independently of each other are selected from Ci-C6-alkyl, C1-C6- haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, Ci-C4-alkoxy-Ci-C4-alkyl and C3-C7- cycloalkyl, which is unsubstituted or partly or completely halogenated, and in particular selected from Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C3-C6- cycloalkyl.

R^3e, R^3f, R^4e, R^4f independently of each other are selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, which is unsubstituted or partially or completely halogenated, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, Ci-C4-alkoxy-Ci-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, Ci-C4-alkyl, C1-C4- haloalkyl and Ci-C4-alkoxy, or R^3e and R^3f 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 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, Ci-C4-alkyl, Ci-C4-haloalkyl and Ci-C4-alkoxy.

More preferably R^3e, R^3f, R^4e, R^4f independently of each other are selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl and benzyl, or R^3e and R^3f 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 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, Ci-C4-alkyl and Ci-C4-haloalkyl.

In particular, R^3e, R^3f, R^4e, R^4f independently of each other are selected from hydrogen and Ci-C4-alkyl, or R^3e and R^3f 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 O, S and N and which is unsubstituted or may carry 1 , 2 or 3 methyl groups.

R¾, R⁴9 independently of each other are selected from hydrogen, Ci-C6-alkyl, C3-C7- cycloalkyl, which is unsubstituted or partly or completely halogenated, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and benzyl.

More preferably R¾, R⁴9 independently of each other are selected from hydrogen, C1-C6- alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, benzyl, Ci-C4-alkoxy-Ci-C4-alkyl and C3-C7-cycloalkyl, which is unsubstituted or partly or completely halogenated, and in particular selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, benzyl and C3-C6-cycloalkyl.

R^3h, R^4h independently of each other are selected from hydrogen, Ci-C6-alkyl, C3-C7- cycloalkyl, which is unsubstituted or partly or completely halogenated, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl, benzyl and a radical C(=0)-R^k, where R^k is H, Ci-C4-alkyl, Ci-C4-haloalkyl or phenyl.

More preferably R^3h, R^4h independently of each other are selected from hydrogen, C1-C6- alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, benzyl, Ci-C4-alkoxy-Ci-C4-alkyl and C3-C7-cycloalkyl, which is unsubstituted or partly or completely halogenated, and in particular selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, benzyl and C3-C6-cycloalkyl; or

R¾ and R^3h or R⁴9 and R^4h 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 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 =0, halogen, Ci-C4-alkyl and Ci-C4-haloalkyl and Ci-C4-alkoxy;

more preferably R¾ and R^3h or R⁴9 and R^4h 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 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, Ci-C4-alkyl and Ci-C4-haloalkyl;

and in particular, R¾ and R^3h or R⁴9 and R^4h 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 O, S and N and which is unsubstituted or may carry 1 , 2 or 3 methyl groups.

R^z is selected from Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C7-cycloalkyl, Ci-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 unsubstitut- ed or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.

Preferably, R^z is selected from of Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-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 halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy. More preferably, R^z is Ci-C4-alkyl, Ci-C3-haloalkyl, Ci-C4-alkoxy, phenyl or benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 or 2 groups, which are identical or different and selected from halogen, Ci-C4-alkyl and Ci-C4-haloalkyl; and in particular R^z is C1-C3- alkyl, Ci-C3-haloalkyl or Ci-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 formula I, and likewise in compounds of the formulae I .A, I.B, I.C and I.D, wherein the variables R¹ and R³ have the following meanings:

R¹ is selected from the group consisting of halogen, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci- C4-alkoxy-Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio, Ci-C4-haloalkylthio and Ci-C4-alkylsulfonyl; in particular from F, CI, Br, I, nitro, CH₃, CF₃, SCH₃, SCF₃, S0₂CH₃ and CH₂OCH₂CH₂OCH₃; and

R³ is selected from the group consisting of halogen, nitro, Ci-C2-alkyl, Ci-C2-haloalkyl, Ci- C₂-haloalkoxy, Ci-C₂-alkylthio, Ci-C₂-haloalkylthio, Ci-C₂-alkyl-S(0), Ci-C₂-haloalkyl-S(0), Ci- C₂-alkyl-S(0)₂ and Ci-C₂-haloalkyl-S(0)₂; in particular from CI, F, Br, I, N0₂, CH₃, CF₃, CHF₂, OCF₃, OCHF₂, SCH₃, SCF₃, SCHF₂, S(0)CH₃, S(0)CH₂CH₃, S(0)₂CH₃ and S(0)₂CH₂CH₃.

Even more preferred are compounds of formula I, and likewise in compounds of the formulae I.A, I.B, I.C and I.D, wherein Q is Q¹, Q², Q³ or Q⁴ and the variables R¹, R², R³, R⁴, R⁵, R^6a, R^6b, R^6c and R^6d have the following meanings:

R¹ is selected from the group consisting of halogen, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci- C4-alkoxy-Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio, Ci-C4-haloalkylthio and Ci-C4-alkylsulfonyl, and in particular from F, CI, Br, I, nitro, CH₃, CF₃, SCH₃ and S0₂CH₃;

R² is is a radical of the formula 2a or a radical of the formula 2b,

where # in formulae 2a and 2b indicates the point of attachment to the oxygen atom bearing R², and wherein

Z² is a bond, linear Ci-C₃-alkandiyl, which is unsubstituted or partly or completely fluorinated or substituted by 1 , 2, 3 or 4 groups selected from Ci-C₃-alkyl; and in particular is a bond, CH₂, CH(CH₃), C(CH₃)₂ or CF₂;

R^2a is hydrogen, Ci-C6-alkyl, Ci-C₃-haloalkyl, C₃-C6-cycloalkyl, benzyl or heterocyclylmethyl, where heterocyclyl in the last mentioned radical is a 5- or 6-membered monocyclic partially unsaturated or aromatic heterocycle, which contains 1 or 2 heteroatoms as ring members, which are selected from the group consisting of O and N; and in particular R^2a is hydrogen, Ci-C6-alkyl, Ci-C₃-haloalkyl, cyclopropyl, benzyl or pyrazol-1 -yl-methyl; R^2b is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C3-haloalkyl, C3-C6- cycloalkyl, Ci-C₃-alkoxy, Ci-C₂-alkyl-0-C(0)-Ci-C₄-alkyl, (Ci-C₂-alkyl)₂N-C(0)-Ci-C₄-alkyl, benzyl and phenyl, which is unsubstituted or substituted by 1 or 2 groups, which are identical or different and selected from the group consisting of methyl, ethyl, methoxy, CI and F; and in particular R^2b is hydrogen, Ci-C6-alkyl, Ci-C3-haloalkyl, cyclopropyl, methoxy, 1 -methyl-1 - (methoxycarbonyl)ethyl, 1 -methyl-1 -(N,N-dimethylaminocarbonyl)ethyl, benzyl or phenyl which is unsubstituted or substituted by 1 or 2 groups selected from methyl, methoxy, CI and F; or

R^2a, R^2b together with the nitrogen atom, to which they are bound form a 5-, 6- or 7- membered, saturated heteromonocyclic radical or form a 7-, 8-, 9- or 10-membered saturated heterobicyclic radical, where the heterobicyclc radical is a fused or a bridged ring system, where the heteromonocyclic or heterobicyclc radical may contain as a ring member a further heteroatom selected from O and N and where the heterocyclic radical is unsubstituted or carries 1 , 2 or 3 groups R^2e or carries 1 group R^2f and 0, 1 or 2 groups R^2e, where R^2e is methyl or ethyl; and R^2f is CH₃-C(0)-, CH₃0-C(0)- or (CH₃)₂N-C(0)-; and in particular R^2a, R^2b together with the nitrogen atom, to which they are bound are morpholin-4-yl, 2- methylmorpholin-4-yl, 3-methylmorpholin-4-yl, 2-ethylmorpholin-4-yl, 2,2-dimethylmorpholin- 4-yl, 3,3-dimethylmorpholin-4-yl, 2,3-dimethylmorpholin-4-yl, 2,5-dimethylmorpholin-4-yl, 2,6- dimethylmorpholin-4-yl, 3,5-dimethylmorpholin-4-yl, 2,6,6-trimethylmorpholin-4-yl, 2,5- diethylmorpholin-4-yl, 2,6-diethylmorpholin-4-yl, pyrrolidin-1 -yl, piperidin-1 -yl, piperazin-1 -yl, 4-methoxycarbonylpiperazin-1 -yl, 4-(N,N-dimethylaminocarbonyl)piperazin-1 -yl, 4- (methylcarbonyl)piperazin-l -yl, 1 ,4-oxazepan-4-yl, 7-methyl-1 ,4-oxazepan-4-yl, 6-oxa-3- azabicyclo[3.1 .1]heptan-3-yl, 8-oxa-3-azabicyclo[3.2.1 ]octan-3-yl or 3,4,4a,5, 6,7,8, 8a- octahydro-2H-benzo[b][1 ,4]oxazin-4-yl;

Z is a covalent bond or linear Ci-C₃-alkanediyl; and in particular Z is CH₂, CH₂CH₂ or

CH₂CH₂CH₂;

R^2c is selected from the group consisting of hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl, and in particular R^2c is hydrogen, methyl, ethyl, CF₃ or CH₂CF₃;

p is 0 or 1 ; and in particular p is 0; and

R^2d is selected from the group consisting of halogen and Ci-C₄-alkyl, an in particular R^2d is methyl, ethyl, chlorine or fluorine;

R³ is selected from halogen, nitro, Ci-C₂-alkyl, Ci-C₂-haloalkyl, Ci-C₂-haloalkoxy, Ci-C₂- alkylthio, Ci-C₂-haloalkylthio, Ci-C₂-alkyl-S(0), Ci-C₂-haloalkyl-S(0), Ci-C₂-alkyl-S(0)₂ and Ci- C₂-haloalkyl-S(0)₂; and in particular from CI, Br, I, CF₃, SCH₃, S(0)CH₃ and S(0)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;

R^6a, R^6b, R^6c, R^6d are, independently of each other, selected from H, CH₃, CH₃CH₂, CH₃CH₂CH₂, CH₃OCH₂CH₂ and CH₃OCH₂; in particular from H, CH₃, CH₃CH₂ and CH₃CH₂CH₂, and are specifically CH₃. Specifically preferred are compounds of formula I, and likewise in compounds of the formulae I .A, I.B, I.C and I.D, wherein Q is Q¹, Q², Q³ or Q⁴ and the variables R¹, R², R³, R⁴, R⁵, R^6a, R^6b, R^6c and R^6d have the following meanings:

R¹ is selected from the group consisting of CI, Br, CH3 and CF3, in particular CI, Br and CH₃;

R² is a radical of the formula 2a or of the formula 2b, wherein

Z² is a bond, CH₂, CH(CH₃), C(CH₃)₂ or CF₂;

R^2a is hydrogen, Ci-C4-alkyl, Ci-C3-haloalkyl, cyclopropyl or pyrazol-1 -yl-methyl;

R^2b is hydrogen, Ci-C6-alkyl, Ci-C3-haloalkyl, cyclopropyl, methoxy, 1 -methyl-1 - (methoxycarbonyl)ethyl, 1 -methyl-1 -(N,N-dimethylaminocarbonyl)ethyl, benzyl, phenyl,

4-chloro-phenyl, 4-fluoro-phenyl, 4-methoxyphenyl or 2,6-dimethyl-phenyl; or

R^2a, R^2b together with the nitrogen atom, to which they are bound form a 5-, 6- or 7- membered, saturated heteromonocyclic radical or form a 7-, 8-, 9- or 10-membered saturated heterobicyclic radical, where the heterobicycic radical is a fused or a bridged ring system, where the heteromonocyclic or heterobicycic radical may contain as a ring member a further heteroatom selected from O and N and where the heterocyclic radical is unsubstituted or carries 1 , 2 or 3 groups R^2e or carries 1 group R^2f and 0, 1 or 2 groups R^2e, where R^2e is methyl or ethyl; and R^2f is CH₃-C(0)-, CH₃0-C(0)- or (CH₃)₂N- C(O)-; and in particular form morpholin-4-yl, 2-methylmorpholin-4-yl, 3- methylmorpholin-4-yl, 2-ethylmorpholin-4-yl, 2,2-dimethylmorpholin-4-yl, 3,3- dimethylmorpholin-4-yl, 2,3-dimethylmorpholin-4-yl, 2,5-dimethylmorpholin-4-yl, 2,6- dimethylmorpholin-4-yl, 3,5-dimethylmorpholin-4-yl, 2,6,6-trimethylmorpholin-4-yl, 2,5- diethylmorpholin-4-yl, 2,6-diethylmorpholin-4-yl, pyrrolidin-1 -yl, piperidin-1 -yl, piperazin- 1 -yl, 4-methoxycarbonylpiperazin-1 -yl, 4-(N,N-dimethylaminocarbonyl)piperazin-1 -yl, 4- (methylcarbonyl)piperazin-l -yl, 1 ,4-oxazepan-4-yl, 7-methly-1 ,4-oxazepan-4-yl, 6-oxa-

3-azabicyclo[3.1.1 ]heptan-3-yl, 8-oxa-3-azabicyclo[3.2.1 ]octan-3-yl or

3,4,4a,5, 6,7,8, 8a-octahydro-2H-benzo[b][1 ,4]oxazin-4-yl;

Z is CH₂, CH₂CH₂ or CH₂CH₂CH₂;

R^2c is H, methyl, ethyl, CF₃ or CH₂CF₃; and

p is 0;

R³ is selected from halogen, nitro, Ci-C₂-alkyl, Ci-C₂-haloalkyl, Ci-C₂-haloalkoxy, C1-C2- alkylthio, Ci-C₂-haloalkylthio, Ci-C₂-alkyl-S(0), Ci-C₂-haloalkyl-S(0), Ci-C₂-alkyl-S(0)₂ and Ci-C₂-haloalkyl-S(0)₂; and in particular from CI, Br, I, CF₃, SCH₃, S(0)CH₃ and S(0)₂CH₃

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

R^6a, R^6b, R^6c, R^6d are, independently of each other, selected from H, CH₃, CH₃CH₂, CH₃CH₂CH₂, CH₃OCH₂CH₂ and CH₃OCH₂; and in particular from H, CH₃, CH₃CH₂ and

CH₃CH₂CH₂, and are specifically CH₃. Specifically preferred are compounds of formula I, and likewise in compounds of the formulae I .A, I.B, I.C and I.D, wherein Q is Q¹, Q², Q³ or Q⁴ and the variables R¹, R², R³, R⁴, R⁵, R^6a, R^6b, R^6c and R^6d have the following meanings:

R¹ is selected from the group consisting of CI, Br and CH3;

R² is a radical of the formula 2a or of the formula 2b, wherein

Z² is a bond, CH₂, CH(CH₃), C(CH₃)₂ or CF₂;

R^2a is hydrogen, Ci-C4-alkyl, Ci-C3-haloalkyl, cyclopropyl or pyrazol-1 -yl -methyl;

R^2b is hydrogen, Ci-C6-alkyl, Ci-C3-haloalkyl, cyclopropyl, methoxy, 1 -methyl-1 - (methoxycarbonyl)ethyl, 1 -methyl-1 -(N,N-dimethylaminocarbonyl)ethyl, benzyl, phenyl, 4-chloro-phenyl, 4-fluoro-phenyl, 4-methoxy-phenyl or 2,6-dimethyl-phenyl; or

R^2a, R^2b together with the nitrogen atom, to which they are bound form a 5-, 6- or 7- membered, saturated heteromonocyclic radical or form a 7-, 8-, 9- or 10-membered saturated heterobicyclic radical, where the heterobicycic radical is a fused or a bridged ring system, where the heteromonocyclic or heterobicycic radical may contain as a ring member a further heteroatom selected from O and N and where the heterocyclic radical is unsubstituted or carries 1 , 2 or 3 groups R^2e or carries 1 group R^2f and 0, 1 or 2 groups R^2e, where R^2e is methyl or ethyl; and R^2f is CH₃-C(0)-, CH₃0-C(0)- or (CH₃)₂N- C(O)-; and in particular form morpholin-4-yl, 2-methylmorpholin-4-yl, 3- methylmorpholin-4-yl, 2-ethylmorpholin-4-yl, 2,2-dimethylmorpholin-4-yl, 3,3- dimethylmorpholin-4-yl, 2,3-dimethylmorpholin-4-yl, 2,5-dimethylmorpholin-4-yl, 2,6- dimethylmorpholin-4-yl, 3,5-dimethylmorpholin-4-yl, 2,6,6-trimethylmorpholin-4-yl, 2,5- diethylmorpholin-4-yl, 2,6-diethylmorpholin-4-yl, pyrrolidin-1 -yl, piperidin-1 -yl, piperazin- 1 -yl, 4-methoxycarbonylpiperazin-1 -yl, 4-(N,N-dimethylaminocarbonyl)piperazin-1 -yl, 4- (methylcarbonyl)piperazin-l -yl, 1 ,4-oxazepan-4-yl, 7-methyl-1 ,4-oxazepan-4-yl, 6-oxa- 3-azabicyclo[3.1.1 ]heptan-3-yl, 8-oxa-3-azabicyclo[3.2.1 ]octan-3-yl or

3,4,4a,5, 6,7,8, 8a-octahydro-2H-benzo[b][1 ,4]oxazin-4-yl;

Z is CH₂, CH₂CH₂ or CH₃CH₂CH₂,;

R^2c is methyl, ethyl, CF₂ or CH₂CF₃; and

p is 0;

R³ is CI, Br, I, CF₃, SCH₃, S(0)CH₃ or S(0)₂CH₃;

R⁴ is hydrogen;

R⁵ is fluorine; and

R^6a is H, CH₃, CH₃CH₂ or CH₃CH₂CH₂, and R^6b, R^6c, R^6d are, independently of each other, methyl.

Very specifically the invention relates to compounds of formula I, and likewise in compounds of the formulae I .A or I.B, wherein Q is Q¹ or Q² and the variables R¹, R², R³, R⁴, R⁵, R^6a and R^6b have the following meanings:

R¹ is CI;

R² is a radical of the formula 2a or of the formula 2b, wherein

Z² is a bond, CH₂ or CH(CH₃); R^2a is hydrogen, Ci-C4-alkyl, Ci-C3-haloalkyl or cyclopropyl;

R^2b is Ci-C5-alkyl, cyclopropyl, phenyl or 4-chloro-phenyl; or

R^2a, R^2b together with the nitrogen atom, to which they are bound form a 6- or 7- membered, saturated heteromonocyclic radical or form a 7- or 8-membered saturated heterobicyclic radical, where the heterobicyclc radical is a bridged ring system, where the heteromonocyclic or heterobicyclc radical may contain as a ring member a further heteroatom selected from O and N and where the heterocyclic radical is unsubstituted or carries 1 , 2 or 3 groups R^2e or carries 1 group R^2f, where R^2e is methyl or ethyl; and R^2f is CH30-C(0)-; and in particular form 2-methylmorpholin-4-yl, 2-ethylmorpholin-4-yl, 2,2-dimethylmorpholin-4-yl, 2,6-dimethylmorpholin-4-yl, 3,5-dimethylmorpholin-4-yl,

2,6,6-trimethylmorpholin-4-yl, 2,5-diethylmorpholin-4-yl, 4-methoxycarbonylpiperazin-1 - yl, 7-methly-1 ,4-oxazepan-4-yl, 6-oxa-3-azabicyclo[3.1 .1]heptan-3-yl, or 8-oxa-3- azabicyclo[3.2.1 ]octan-3-yl;

Z is Chb or CH₂CH₂;

R^2c is H, methyl or CH₂CF₃; and

p is 0;

R³ is CI, Br, I, CF₃, SCH₃ or S(0)₂CH₃;

R⁴ is hydrogen;

R⁵ is fluorine; and

R^6a is CH₃ or CH₃CH₂, and R^6b is methyl.

Examples of preferred compounds are the individual compounds compiled in the Tables 1 to 48 below. Moreover, the meanings mentioned below for the individual variables in the Tables 1 to 48 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 ¹, R⁴ is CI, R^6a is methyl:

Table 1 : Compounds of formula I.A.I (I.A.I.1 - I.AI.4716) in which the combination of R¹,

R², R³and R⁵ for a compound corresponds in each case to one row of Table A;

Compounds I.A.II, wherein Q is Q¹, R⁴ is CI, R^6a is ethyl:

I.A.II

Table 2: Compounds of formula I.A.II (I.A.II.1 - I.A.II.4716) in which the combination of R¹ R², R³ and R⁵ for a compound corresponds in each case to one row of Table A;

Compounds I.A.III, wherein ¹, R⁴ is F, R^6a is methyl:

Table 3: Compounds of formula I.A.III (I.A.III.1 - I.A.III.4716) in which the combination of R¹, R², R³ and R⁵ for a compound corresponds in each case to one row of Table A;

Compounds I.A.IV, wherei ¹, R⁴ is F, R^6a is ethyl:

Table 4: Compounds of formula I.A.IV (I.A.IV.1 - I.A.IV.4716) in which the combination of R¹, R², R³ and R⁵ for a compound corresponds in each case to one row of Table A;

Compounds I.A.V, wherein Q is Q¹, R⁴ is H, R^6a is methyl:

Table 5: Compounds of formula I.A.V (I.A.V.1 - I.A.V.4716) in which the combination of R R², R³ and R⁵ for a compound corresponds in each case to one row of Table A;

Compounds I.A.VI, wherein Q is Q¹, R⁴ is H, R^6a is ethyl:

Table 6: Compounds of formula I.A.VI (I.A.VI.1 - I.A.VI.4716) in which the combination of R¹, R², R³ and R⁵ for a compound corresponds in each case to one row of Table A;

Compounds I.A.VI I, wherein Q is Q¹, R⁴ is CI, R^6a is n- ropyl:

I.A.VII

Table 7: Compounds of formula I.A.VII (I.A.VI 1.1 - I.A.VI 1.4716) in which the combination of R¹, R², R³and R⁵ for a compound corresponds in each case to one row of Table A;

Compounds I.A.VI II, wherein Q is Q¹, R⁴ is F, R^6a is n- ropyl:

Table 8: Compounds of formula I.A.VIII (I.A.VIII.1 - I.A.VIII.4716) in which the combination of R¹, R², R³and R⁵ for a compound corresponds in each case to one row of Table A;

Compounds I.A.IX, wherein Q is Q¹ R⁴ is H, R^6a is n-propyl:

Table 9: Compounds of formula I.A.IX (I.A.IX.1 - I.A.IX.4716) in which the combination of R¹, R², R³and R⁵ for a compound corresponds in each case to one row of Table A; Compounds I.A.X, wherein is Q¹, R⁴ is CI, R^6a is H:

Table 10: Compounds of formula I.A.X (I.A.X.1 - I.A.X.4716) in which the combination of R¹, R², R³and R⁵ for a compound corresponds in each case to one row of Table A;

Compounds I.A.XI, wherein Q is Q¹ R⁴ is F, R^6a is H:

Table 1 1 : Compounds of formula I .A.XI (I .A.XI .1 - 1.A.XI .4716) in which the combination of R¹, R², R³and R⁵ for a compound corresponds in each case to one row of Table A;

Compounds I.A.XII, wherein Q is Q¹ R⁴ is H, R^6a is H

Table 12: Compounds of formula I.A.XII (I. A.XI 1.1 - 1. A.XI 1.4716) in which the combination of R¹, R², R³and R⁵ for a compound corresponds in each case to one row of Table A;

Compounds I.B.I, wherein Q ², R⁴ is CI, R^6b is methyl:

Table 13: Compounds of formula I.B.I (I.B.1.1 - I.B.I.3420) in which the combination of R¹, R², R³ and R⁵ for a compound corresponds in each case to one row of Table A; Compounds I.B.II, wherein ², R⁴ is CI, R^6b is ethyl:

Table 14: Compounds of formula I.B.II (I.B.II.1 - I.B.II.3420) in which the combination of R¹, R², R³ and R⁵for a compound corresponds in each case to one row of Table A;

Compounds I.B.III, wherein ², R⁴ is F, R^6b is methyl:

Table 15: Compounds of formula I.B.III (I.B.III.1 - I.B.III.3420) in which the combination of R¹, R², R³ and R⁵ for a compound corresponds in each case to one row of Table A;

Compounds I.B.IV, wherei ², R⁴ is F, R^6b is ethyl:

Table 16: Compounds of formula I.B.IV (I.B.IV.1 - I.B.IV.3420) in which the combination of R¹, R², R³ and R⁵ for a compound corresponds in each case to one row of Table A;

Compounds I.B.V, wherein ², R⁴ is H, R^6b is methyl:

Table 17: Compounds of formula I.B.V (I.B.V.1 - I.B.V.3420) in which the combination of R¹, R², R³ and R⁵ for a compound corresponds in each case to one row of Table A; Compounds I.B.VI, wherein Q is Q², R⁴ is H, R^6b is ethyl:

Table 18: Compounds of formula I.B.VI (I.B.VI.1 - I.B.VI.3420) in which the combination of R¹, R², R³ and R⁵ for a compound corresponds in each case to one row of Table A;

Compounds I.B.VII, wherein Q is Q¹, R⁴ is CI, R^6b is n-propyl:

Table 19: Compounds of formula I.B.VII (I.B.VII.1 - I.B.VII.4716) in which the combination of R¹, R², R³and R⁵ for a compound corresponds in each case to one row of Table A;

Compounds I.B.VIII, wherein Q is Q¹, R⁴ is F, R^6b is n-propyl:

Table 20: Compounds of formula I.B.VIII (I.B.VIII.1 - I.B.VIII.4716) in which the combination of R¹, R², R³and R⁵ for a compound corresponds in each case to one row of Table A;

Compounds I.B.IX, wherein Q is Q¹ R⁴ is H, R^6b is n-propyl:

Table 21 : Compounds of formula I.B.IX (I.B.IX.1 - I.B.IX.4716) in which the combination of R¹, R², R³and R⁵ for a compound corresponds in each case to one row of Table A; Compounds I.B.X, wherein is Q¹, R⁴ is CI, R^6b is H:

Table 22: Compounds of formula I.B.X (I.B.X.1 - I.B.X.4716) in which the combination of R¹, R², R³and R⁵ for a compound corresponds in each case to one row of Table A;

Compounds I.B.XI, wherein Q is Q¹ R⁴ is F, R^6b is H:

Table 23: Compounds of formula I.B.XI (I.B.XI.1 - I.B.XI.4716) in which the combination of R¹, R², R³and R⁵ for a compound corresponds in each case to one row of Table A;

Compounds I.B.XII, wherein Q is Q¹ R⁴ is H, R^6b is H:

Table 24: Compounds of formula I.B.XII (I.B.XII.1 - I.B.XII.4716) in which the combination of R¹, R², R³and R⁵ for a compound corresponds in each case to one row of Table A;

Compounds I.C.I, wherein Q is Q³, R⁴ is CI, R^6c is methyl:

Table 25: Compounds of formula I.C.I (I .C.I .1 - 1. C.1.4716) in which the combination of R¹, R², R³ and R⁵ for a compound corresponds in each case to one row of Table A; Compounds I. CM, wherein ³, R⁴ is CI, R^6c is ethyl:

Table 26: Compounds of formula 1.0.11 (I.C.II.1 - 1. C.11.4716) in which the combination of R¹, R², R³ and R⁵ for a compound corresponds in each case to one row of Table A;

Compounds I.C.III, wherein ³, R⁴ is F, R^6c is methyl:

Table 27: Compounds of formula I.C.III (I.C.III.1 - 1. C.111.4716) in which the combination of R¹, R², R³ and R⁵ for a compound corresponds in each case to one row of Table A;

Compounds I. CIV, wherein Q is Q³, R⁴ is F, R^6c is ethyl:

Table 28: Compounds of formula I.C.IV (I.C.IV.1 - I.C.IV.4716) in which the combination of R¹, R², R³ and R⁵ for a compound corresponds in each case to one row of Table A;

Compounds I.C.V, wherein Q is Q³, R⁴ is H, R^6c is methyl:

Table 29: Compounds of formula I.C.V (I.C.V.1 - I.C.V.4716) in which the combination of R¹, R², R³ and R⁵ for a compound corresponds in each case to one row of Table A; Compounds I.C.VI, wherei ³, R⁴ is H, R^6c is ethyl:

Table 30: Compounds of formula I.C.VI (I.C.VI.1 - I.C.VI.4716) in which the combination of R¹, R², R³ and R⁵ for a compound corresponds in each case to one row of Table A;

Compounds I.C.VI I, wherein Q is Q³, R⁴ is CI, R^6c is n- ropyl:

Table 31 : Compounds of formula I.C.VII (I.C.VII.1 - I.C.VII.4716) in which the combination of R¹, R², R³ and R⁵ for a compound corresponds in each case to one row of Table A;

Compounds I.C.VIII, wherein Q is Q³, R⁴ is F, R^6c is n- ropyl:

Table 32: Compounds of formula I.C.VIII (I.C.VIII.1 - I.C.VIII.4716) in which the combination of R¹, R², R³ and R⁵ for a compound corresponds in each case to one row of Table A;

Compounds I.C.IX, wherein Q is Q³ R⁴ is H, R^6c is n-propyl:

Table 33: Compounds of formula I.C.IX (I.C.IX.1 - I.C.IX.4716) in which the combination of R¹, R², R³ and R⁵ for a compound corresponds in each case to one row of Table A; Compounds I.C.X, wherein Q is Q³ R⁴ is CI, R^6c is H:

Table 34: Compounds of formula I.C.X (I.C.X.1 - I.C.X.4716) in which the combination of R¹, R², R³ and R⁵ for a compound corresponds in each case to one row of Table A;

Compounds I. CXI, wherein Q is Q³ R⁴ is F, R^6c is H:

Table 35: Compounds of formula I.C.XI (I.C.XI.1 - I.C.XI.4716) in which the combination of R¹, R², R³ and R⁵ for a compound corresponds in each case to one row of Table A;

Compounds I .CXI I , wherein Q is Q³, R⁴ is H, R^6c is H:

Table 36: Compounds of formula I.C.XII (I.C.XII.1 - I.C.XII.4716) in which the combination of R¹, R², R³ and R⁵ for a compound corresponds in each case to one row of Table A;

Compounds I.D.I, wherein ⁴, R⁴ is CI, R^6d is methyl

I.D.I Table 37: Compounds of formula I.D.I (I.D.1.1 - 1. D.1.4716) in which the combination of R¹, R², R³ and R⁵ for a compound corresponds in each case to one row of Table A;

Compounds I.D.II, wherein ⁴, R⁴ is CI, R^6d is ethyl:

Table 38: Compounds of formula I.D.II (I. D.11.1 - 1. D.11.4716) in which the combination of R¹, R², R³ and R⁵ for a compound corresponds in each case to one row of Table A;

Compounds I.D.III, wherei ⁴, R⁴ is F, R^6d is methyl:

Table 39: Compounds of formula I.D.III (I.D.III.1 - 1. D.111.4716) in which the combination of R¹, R², R³ and R⁵ for a compound corresponds in each case to one row of Table A;

Compounds I.D.IV, wherein Q is Q⁴, R⁴ is F, R^6d is ethyl:

I.D.IV

Table 40: Compounds of formula I.D.IV (I.D.IV.1 - I.D.IV.4716) in which the combination of R¹, R², R³ and R⁵ for a compound corresponds in each case to one row of Table A;

Compounds I.D.V, wherein Q is Q⁴, R⁴ is H, R^6d is methyl:

I.D.V Table 41 : Compounds of formula I.D.V (I.D.V.1 - I.D.V.4716) in which the combination of R¹, R², R³ and R⁵ for a compound corresponds in each case to one row of Table A;

Compounds I.D.VI, wher ⁴, R⁴ is H, R^6d is ethyl:

Table 42: Compounds of formula I.D.VI (I.D.VI.1 - I.D.VI.4716) in which the combination of R¹, R², R³ and R⁵ for a compound corresponds in each case to one row of Table A.

Compounds I.D.VII, wherein Q is Q⁴, R⁴ is CI, R^6d is n-propyl

Table 43: Compounds of formula I.D.VII (I.D.VII .1 - I.D.VII.4716) in which the combination of R¹, R², R³ and R⁵ for a compound corresponds in each case to one row of Table A;

Compounds I.D.VIII, wherein Q is Q⁴ R⁴ is F, R^6d is n-propyl

Table 44: Compounds of formula I.D.VIII (I.D.VIII.1 - I.D.VIII.4716) in which the combination of R¹, R², R³ and R⁵ for a compound corresponds in each case to one row of Table A;

Compounds I.D.IX, wherein Q is Q⁴ R⁴ is H, R^6d is n-propyl

Table 45: Compounds of formula I.D.IX (I.D.IX.1 - I.D.IX.4716) in which the combination of R¹, R², R³ and R⁵ for a compound corresponds in each case to one row of Table A; Compounds I.D.X, wherein Q is Q⁴, R⁴ is CI, R^6d is H

Table 46: Compounds of formula I.D.X (I.D.X.1 - I.D.X.4716) in which the combination of R¹, R², R³ and R⁵ for a compound corresponds in each case to one row of Table A;

Compounds I.D.XI, wherein Q is Q⁴, R⁴ is F, R^6d is H

Table 47: Compounds of formula I.D.XI (I.D.XI.1 - I.D.XI.4716) in which the combination of R¹, R², R³ and R⁵ for a compound corresponds in each case to one row of Table A;

Compounds I.D.XII, wherein Q is Q⁴ R⁴ is H, R^6d is H

Table 48: Compounds of formula I.D.XII (I.D.XII.1 - I.D.XII.4716) in which the combination of R¹, R², R³ and R⁵ for a compound corresponds in each case to one row of Table A;

Table A: With regard to R², the substituents R²(1 ) to R²(131 ) are as defined in Table A-1 below.

No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

1 . CI R²(1 ) CI F 6. CI R²(6) CI F

2. CI R²(2) CI F 7. CI R²(7) CI F

3. CI R²(3) CI F 8. CI R²(8) CI F

4. CI R²(4) CI F 9. CI R²(9) CI F

5. CI R²(5) CI F 10. CI R²(10) CI F No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

1 1 . CI R2(1 1 ) CI F 46. CI R2(46) CI F

12. CI R2(12) CI F 47. CI R2(47) CI F

13. CI R2(13) CI F 48. CI R2(48) CI F

14. CI R2(14) CI F 49. CI R2(49) CI F

15. CI R2(15) CI F 50. CI R2(50) CI F

16. CI R2(16) CI F 51 . CI R2(51 ) CI F

17. CI R2(17) CI F 52. CI R2(52) CI F

18. CI R2(18) CI F 53. CI R2(53) CI F

19. CI R2(19) CI F 54. CI R2(54) CI F

20. CI R2(20) CI F 55. CI R2(55) CI F

21 . CI R2(21 ) CI F 56. CI R2(56) CI F

22. CI R2(22) CI F 57. CI R2(57) CI F

23. CI R2(23) CI F 58. CI R2(58) CI F

24. CI R2(24) CI F 59. CI R2(59) CI F

25. CI R2(25) CI F 60. CI R2(60) CI F

26. CI R2(26) CI F 61 . CI R2(61 ) CI F

27. CI R2(27) CI F 62. CI R2(62) CI F

28. CI R2(28) CI F 63. CI R2(63) CI F

29. CI R2(29) CI F 64. CI R2(64) CI F

30. CI R2(30) CI F 65. CI R2(65) CI F

31 . CI R2(31 ) CI F 66. CI R2(66) CI F

32. CI R2(32) CI F 67. CI R2(67) CI F

33. CI R2(33) CI F 68. CI R2(68) CI F

34. CI R2(34) CI F 69. CI R2(69) CI F

35. CI R2(35) CI F 70. CI R2(70) CI F

36. CI R2(36) CI F 71 . CI R2(71 ) CI F

37. CI R2(37) CI F 72. CI R2(72) CI F

38. CI R2(38) CI F 73. CI R2(73) CI F

39. CI R2(39) CI F 74. CI R2(74) CI F

40. CI R2(40) CI F 75. CI R2(75) CI F

41 . CI R2(41 ) CI F 76. CI R2(76) CI F

42. CI R2(42) CI F 77. CI R2(77) CI F

43. CI R2(43) CI F 78. CI R2(78) CI F

44. CI R2(44) CI F 79. CI R2(79) CI F

45. CI R2(45) CI F 80. CI R2(80) CI F No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

81 . CI R²(81 ) CI F 1 16. CI R2(33) CI CI

82. CI R²(82) CI F 1 17. CI R2(34) CI CI

83. CI R²(83) CI F 1 18. CI R2(35) CI CI

84. CI R2(1 ) CI CI 1 19. CI R2(36) CI CI

85. CI R2(2) CI CI 120. CI R2(37) CI CI

86. CI R2(3) CI CI 121 . CI R2(38) CI CI

87. CI R2(4) CI CI 122. CI R2(39) CI CI

88. CI R2(5) CI CI 123. CI R2(40) CI CI

89. CI R2(6) CI CI 124. CI R2(41 ) CI CI

90. CI R2(7) CI CI 125. CI R2(42) CI CI

91 . CI R2(8) CI CI 126. CI R2(43) CI CI

92. CI R2(9) CI CI 127. CI R2(44) CI CI

93. CI R2(10) CI CI 128. CI R2(45) CI CI

94. CI R2(1 1 ) CI CI 129. CI R2(46) CI CI

95. CI R2(12) CI CI 130. CI R2(47) CI CI

96. CI R2(13) CI CI 131 . CI R2(48) CI CI

97. CI R2(14) CI CI 132. CI R2(49) CI CI

98. CI R2(15) CI CI 133. CI R2(50) CI CI

99. CI R2(16) CI CI 134. CI R2(51 ) CI CI

100. CI R2(17) CI CI 135. CI R2(52) CI CI

101 . CI R2(18) CI CI 136. CI R2(53) CI CI

102. CI R2(19) CI CI 137. CI R2(54) CI CI

103. CI R2(20) CI CI 138. CI R2(55) CI CI

104. CI R2(21 ) CI CI 139. CI R2(56) CI CI

105. CI R2(22) CI CI 140. CI R2(57) CI CI

106. CI R2(23) CI CI 141 . CI R2(58) CI CI

107. CI R2(24) CI CI 142. CI R2(59) CI CI

108. CI R2(25) CI CI 143. CI R2(60) CI CI

109. CI R2(26) CI CI 144. CI R2(61 ) CI CI

1 10. CI R2(27) CI CI 145. CI R2(62) CI CI

1 1 1 . CI R2(28) CI CI 146. CI R2(63) CI CI

1 12. CI R2(29) CI CI 147. CI R2(64) CI CI

1 13. CI R2(30) CI CI 148. CI R2(65) CI CI

1 14. CI R2(31 ) CI CI 149. CI R2(66) CI CI

1 15. CI R2(32) CI CI 150. CI R2(67) CI CI No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

151 . CI R²(68) CI CI 186. CI R²(20) Br F

152. CI R²(69) CI CI 187. CI R²(21 ) Br F

153. CI R²(70) CI CI 188. CI R²(22) Br F

154. CI R²(71 ) CI CI 189. CI R²(23) Br F

155. CI R²(72) CI CI 190. CI R²(24) Br F

156. CI R²(73) CI CI 191 . CI R²(25) Br F

157. CI R²(74) CI CI 192. CI R²(26) Br F

158. CI R²(75) CI CI 193. CI R²(27) Br F

159. CI R²(76) CI CI 194. CI R²(28) Br F

160. CI R²(77) CI CI 195. CI R²(29) Br F

161 . CI R²(78) CI CI 196. CI R²(30) Br F

162. CI R²(79) CI CI 197. CI R²(31 ) Br F

163. CI R²(80) CI CI 198. CI R²(32) Br F

164. CI R²(81 ) CI CI 199. CI R²(33) Br F

165. CI R²(82) CI CI 200. CI R²(34) Br F

166. CI R²(83) CI CI 201 . CI R²(35) Br F

167. CI R²(1 ) Br F 202. CI R²(36) Br F

168. CI R²(2) Br F 203. CI R²(37) Br F

169. CI R²(3) Br F 204. CI R²(38) Br F

170. CI R²(4) Br F 205. CI R²(39) Br F

171 . CI R²(5) Br F 206. CI R²(40) Br F

172. CI R²(6) Br F 207. CI R²(41 ) Br F

173. CI R²(7) Br F 208. CI R²(42) Br F

174. CI R²(8) Br F 209. CI R²(43) Br F

175. CI R²(9) Br F 210. CI R²(44) Br F

176. CI R²(10) Br F 21 1 . CI R²(45) Br F

177. CI R²(1 1 ) Br F 212. CI R²(46) Br F

178. CI R²(12) Br F 213. CI R²(47) Br F

179. CI R²(13) Br F 214. CI R²(48) Br F

180. CI R²(14) Br F 215. CI R²(49) Br F

181 . CI R²(15) Br F 216. CI R²(50) Br F

182. CI R²(16) Br F 217. CI R²(51 ) Br F

183. CI R²(17) Br F 218. CI R²(52) Br F

184. CI R²(18) Br F 219. CI R²(53) Br F

185. CI R²(19) Br F 220. CI R²(54) Br F No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

221 . CI R²(55) Br F 256. CI R²(7) Br CI

222. CI R²(56) Br F 257. CI R²(8) Br CI

223. CI R²(57) Br F 258. CI R²(9) Br CI

224. CI R²(58) Br F 259. CI R²(10) Br CI

225. CI R²(59) Br F 260. CI R2(1 1 ) Br CI

226. CI R²(60) Br F 261 . CI R²(12) Br CI

227. CI R²(61 ) Br F 262. CI R²(13) Br CI

228. CI R²(62) Br F 263. CI R²(14) Br CI

229. CI R²(63) Br F 264. CI R²(15) Br CI

230. CI R²(64) Br F 265. CI R²(16) Br CI

231 . CI R²(65) Br F 266. CI R²(17) Br CI

232. CI R²(66) Br F 267. CI R²(18) Br CI

233. CI R²(67) Br F 268. CI R²(19) Br CI

234. CI R²(68) Br F 269. CI R²(20) Br CI

235. CI R²(69) Br F 270. CI R²(21 ) Br CI

236. CI R²(70) Br F 271 . CI R²(22) Br CI

237. CI R²(71 ) Br F 272. CI R²(23) Br CI

238. CI R²(72) Br F 273. CI R²(24) Br CI

239. CI R²(73) Br F 274. CI R²(25) Br CI

240. CI R²(74) Br F 275. CI R²(26) Br CI

241 . CI R²(75) Br F 276. CI R²(27) Br CI

242. CI R²(76) Br F 277. CI R²(28) Br CI

243. CI R²(77) Br F 278. CI R²(29) Br CI

244. CI R²(78) Br F 279. CI R²(30) Br CI

245. CI R²(79) Br F 280. CI R²(31 ) Br CI

246. CI R²(80) Br F 281 . CI R²(32) Br CI

247. CI R²(81 ) Br F 282. CI R²(33) Br CI

248. CI R²(82) Br F 283. CI R²(34) Br CI

249. CI R²(83) Br F 284. CI R²(35) Br CI

250. CI R²(1 ) Br CI 285. CI R²(36) Br CI

251 . CI R²(2) Br CI 286. CI R²(37) Br CI

252. CI R²(3) Br CI 287. CI R²(38) Br CI

253. CI R²(4) Br CI 288. CI R²(39) Br CI

254. CI R²(5) Br CI 289. CI R²(40) Br CI

255. CI R²(6) Br CI 290. CI R²(41 ) Br CI No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

291 . CI R2(42) Br CI 326. CI R²(77) Br CI

292. CI R²(43) Br CI 327. CI R²(78) Br CI

293. CI R2(44) Br CI 328. CI R²(79) Br CI

294. CI R²(45) Br CI 329. CI R²(80) Br CI

295. CI R²(46) Br CI 330. CI R²(81 ) Br CI

296. CI R²(47) Br CI 331 . CI R²(82) Br CI

297. CI R²(48) Br CI 332. CI R²(83) Br CI

298. CI R²(49) Br CI 333. CI R²(1 ) CFs F

299. CI R²(50) Br CI 334. CI R²(2) CFs F

300. CI R²(51 ) Br CI 335. CI R²(3) CFs F

301 . CI R²(52) Br CI 336. CI R²(4) CFs F

302. CI R²(53) Br CI 337. CI R²(5) CFs F

303. CI R²(54) Br CI 338. CI R²(6) CFs F

304. CI R²(55) Br CI 339. CI R²(7) CFs F

305. CI R²(56) Br CI 340. CI R²(8) CFs F

306. CI R²(57) Br CI 341 . CI R²(9) CFs F

307. CI R²(58) Br CI 342. CI R²(10) CFs F

308. CI R²(59) Br CI 343. CI R2(1 1 ) CFs F

309. CI R²(60) Br CI 344. CI R²(12) CFs F

310. CI R²(61 ) Br CI 345. CI R²(13) CFs F

31 1 . CI R²(62) Br CI 346. CI R²(14) CFs F

312. CI R²(63) Br CI 347. CI R²(15) CFs F

313. CI R²(64) Br CI 348. CI R²(16) CFs F

314. CI R²(65) Br CI 349. CI R²(17) CFs F

315. CI R²(66) Br CI 350. CI R²(18) CFs F

316. CI R²(67) Br CI 351 . CI R²(19) CFs F

317. CI R²(68) Br CI 352. CI R²(20) CFs F

318. CI R²(69) Br CI 353. CI R²(21 ) CFs F

319. CI R²(70) Br CI 354. CI R²(22) CFs F

320. CI R²(71 ) Br CI 355. CI R²(23) CFs F

321 . CI R²(72) Br CI 356. CI R²(24) CFs F

322. CI R²(73) Br CI 357. CI R²(25) CFs F

323. CI R²(74) Br CI 358. CI R²(26) CFs F

324. CI R²(75) Br CI 359. CI R²(27) CFs F

325. CI R²(76) Br CI 360. CI R²(28) CFs F No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

361 . CI R²(29) CFs F 396. CI R²(64) CFs F

362. CI R²(30) CFs F 397. CI R²(65) CFs F

363. CI R²(31 ) CFs F 398. CI R²(66) CFs F

364. CI R²(32) CFs F 399. CI R²(67) CFs F

365. CI R²(33) CFs F 400. CI R²(68) CFs F

366. CI R²(34) CFs F 401 . CI R²(69) CFs F

367. CI R²(35) CFs F 402. CI R²(70) CFs F

368. CI R²(36) CFs F 403. CI R²(71 ) CFs F

369. CI R²(37) CFs F 404. CI R²(72) CFs F

370. CI R²(38) CFs F 405. CI R²(73) CFs F

371 . CI R²(39) CFs F 406. CI R²(74) CFs F

372. CI R²(40) CFs F 407. CI R²(75) CFs F

373. CI R²(41 ) CFs F 408. CI R²(76) CFs F

374. CI R²(42) CFs F 409. CI R²(77) CFs F

375. CI R²(43) CFs F 410. CI R²(78) CFs F

376. CI R²(44) CFs F 41 1 . CI R²(79) CFs F

377. CI R²(45) CFs F 412. CI R²(80) CFs F

378. CI R²(46) CFs F 413. CI R²(81 ) CFs F

379. CI R²(47) CFs F 414. CI R²(82) CFs F

380. CI R²(48) CFs F 415. CI R²(83) CFs F

381 . CI R²(49) CFs F 416. CI R²(1 ) CFs CI

382. CI R²(50) CFs F 417. CI R²(2) CFs CI

383. CI R²(51 ) CFs F 418. CI R²(3) CFs CI

384. CI R²(52) CFs F 419. CI R²(4) CFs CI

385. CI R²(53) CFs F 420. CI R²(5) CFs CI

386. CI R²(54) CFs F 421 . CI R²(6) CFs CI

387. CI R²(55) CFs F 422. CI R²(7) CFs CI

388. CI R²(56) CFs F 423. CI R²(8) CFs CI

389. CI R²(57) CFs F 424. CI R²(9) CFs CI

390. CI R²(58) CFs F 425. CI R²(10) CFs CI

391 . CI R²(59) CFs F 426. CI R2(1 1 ) CFs CI

392. CI R²(60) CFs F 427. CI R²(12) CFs CI

393. CI R²(61 ) CFs F 428. CI R²(13) CFs CI

394. CI R²(62) CFs F 429. CI R²(14) CFs CI

395. CI R²(63) CFs F 430. CI R²(15) CFs CI No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

431 . CI R²(16) CFs CI 466. CI R²(51 ) CFs CI

432. CI R2(17) CFs CI 467. CI R²(52) CFs CI

433. CI R²(18) CFs CI 468. CI R²(53) CFs CI

434. CI R²(19) CFs CI 469. CI R²(54) CFs CI

435. CI R²(20) CFs CI 470. CI R²(55) CFs CI

436. CI R²(21 ) CFs CI 471 . CI R²(56) CFs CI

437. CI R²(22) CFs CI 472. CI R²(57) CFs CI

438. CI R²(23) CFs CI 473. CI R²(58) CFs CI

439. CI R²(24) CFs CI 474. CI R²(59) CFs CI

440. CI R²(25) CFs CI 475. CI R²(60) CFs CI

441 . CI R²(26) CFs CI 476. CI R²(61 ) CFs CI

442. CI R²(27) CFs CI 477. CI R²(62) CFs CI

443. CI R²(28) CFs CI 478. CI R²(63) CFs CI

444. CI R²(29) CFs CI 479. CI R²(64) CFs CI

445. CI R²(30) CFs CI 480. CI R²(65) CFs CI

446. CI R²(31 ) CFs CI 481 . CI R²(66) CFs CI

447. CI R²(32) CFs CI 482. CI R²(67) CFs CI

448. CI R²(33) CFs CI 483. CI R²(68) CFs CI

449. CI R²(34) CFs CI 484. CI R²(69) CFs CI

450. CI R²(35) CFs CI 485. CI R²(70) CFs CI

451 . CI R²(36) CFs CI 486. CI R²(71 ) CFs CI

452. CI R²(37) CFs CI 487. CI R²(72) CFs CI

453. CI R²(38) CFs CI 488. CI R²(73) CFs CI

454. CI R²(39) CFs CI 489. CI R²(74) CFs CI

455. CI R²(40) CFs CI 490. CI R²(75) CFs CI

456. CI R²(41 ) CFs CI 491 . CI R²(76) CFs CI

457. CI R²(42) CFs CI 492. CI R²(77) CFs CI

458. CI R²(43) CFs CI 493. CI R²(78) CFs CI

459. CI R²(44) CFs CI 494. CI R²(79) CFs CI

460. CI R²(45) CFs CI 495. CI R²(80) CFs CI

461 . CI R²(46) CFs CI 496. CI R²(81 ) CFs CI

462. CI R²(47) CFs CI 497. CI R²(82) CFs CI

463. CI R²(48) CFs CI 498. CI R²(83) CFs CI

464. CI R²(49) CFs CI 499. CI R²(1 ) SCHs F

465. CI R²(50) CFs CI 500. CI R²(2) SCHs F No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

501 . CI R2(3) SCHs F 536. CI R2(38) SCHs F

502. CI R2(4) SCHs F 537. CI R2(39) SCHs F

503. CI R2(5) SCHs F 538. CI R2(40) SCHs F

504. CI R2(6) SCHs F 539. CI R2(41 ) SCHs F

505. CI R2(7) SCHs F 540. CI R2(42) SCHs F

506. CI R2(8) SCHs F 541 . CI R2(43) SCHs F

507. CI R2(9) SCHs F 542. CI R2(44) SCHs F

508. CI R2(10) SCHs F 543. CI R2(45) SCHs F

509. CI R2(1 1 ) SCHs F 544. CI R2(46) SCHs F

510. CI R2(12) SCHs F 545. CI R2(47) SCHs F

51 1 . CI R2(13) SCHs F 546. CI R2(48) SCHs F

512. CI R2(14) SCHs F 547. CI R2(49) SCHs F

513. CI R2(15) SCHs F 548. CI R2(50) SCHs F

514. CI R2(16) SCHs F 549. CI R2(51 ) SCHs F

515. CI R2(17) SCHs F 550. CI R2(52) SCHs F

516. CI R2(18) SCHs F 551 . CI R2(53) SCHs F

517. CI R2(19) SCHs F 552. CI R2(54) SCHs F

518. CI R2(20) SCHs F 553. CI R2(55) SCHs F

519. CI R2(21 ) SCHs F 554. CI R2(56) SCHs F

520. CI R2(22) SCHs F 555. CI R2(57) SCHs F

521 . CI R2(23) SCHs F 556. CI R2(58) SCHs F

522. CI R2(24) SCHs F 557. CI R2(59) SCHs F

523. CI R2(25) SCHs F 558. CI R2(60) SCHs F

524. CI R2(26) SCHs F 559. CI R2(61 ) SCHs F

525. CI R2(27) SCHs F 560. CI R2(62) SCHs F

526. CI R2(28) SCHs F 561 . CI R2(63) SCHs F

527. CI R2(29) SCHs F 562. CI R2(64) SCHs F

528. CI R2(30) SCHs F 563. CI R2(65) SCHs F

529. CI R2(31 ) SCHs F 564. CI R2(66) SCHs F

530. CI R2(32) SCHs F 565. CI R2(67) SCHs F

531 . CI R2(33) SCHs F 566. CI R2(68) SCHs F

532. CI R2(34) SCHs F 567. CI R2(69) SCHs F

533. CI R2(35) SCHs F 568. CI R2(70) SCHs F

534. CI R2(36) SCHs F 569. CI R2(71 ) SCHs F

535. CI R2(37) SCHs F 570. CI R2(72) SCHs F No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

571 . CI R²(73) SCHs F 606. CI R²(25) SCHs CI

572. CI R2(74) SCHs F 607. CI R²(26) SCHs CI

573. CI R²(75) SCHs F 608. CI R²(27) SCHs CI

574. CI R²(76) SCHs F 609. CI R²(28) SCHs CI

575. CI R2(77) SCHs F 610. CI R²(29) SCHs CI

576. CI R²(78) SCHs F 61 1 . CI R²(30) SCHs CI

577. CI R²(79) SCHs F 612. CI R²(31 ) SCHs CI

578. CI R²(80) SCHs F 613. CI R²(32) SCHs CI

579. CI R²(81 ) SCHs F 614. CI R²(33) SCHs CI

580. CI R²(82) SCHs F 615. CI R²(34) SCHs CI

581 . CI R²(83) SCHs F 616. CI R²(35) SCHs CI

582. CI R²(1 ) SCHs CI 617. CI R²(36) SCHs CI

583. CI R²(2) SCHs CI 618. CI R²(37) SCHs CI

584. CI R²(3) SCHs CI 619. CI R²(38) SCHs CI

585. CI R²(4) SCHs CI 620. CI R²(39) SCHs CI

586. CI R²(5) SCHs CI 621 . CI R²(40) SCHs CI

587. CI R²(6) SCHs CI 622. CI R²(41 ) SCHs CI

588. CI R²(7) SCHs CI 623. CI R²(42) SCHs CI

589. CI R²(8) SCHs CI 624. CI R²(43) SCHs CI

590. CI R²(9) SCHs CI 625. CI R²(44) SCHs CI

591 . CI R²(10) SCHs CI 626. CI R²(45) SCHs CI

592. CI R²(1 1 ) SCHs CI 627. CI R²(46) SCHs CI

593. CI R²(12) SCHs CI 628. CI R²(47) SCHs CI

594. CI R²(13) SCHs CI 629. CI R²(48) SCHs CI

595. CI R²(14) SCHs CI 630. CI R²(49) SCHs CI

596. CI R²(15) SCHs CI 631 . CI R²(50) SCHs CI

597. CI R²(16) SCHs CI 632. CI R²(51 ) SCHs CI

598. CI R²(17) SCHs CI 633. CI R²(52) SCHs CI

599. CI R²(18) SCHs CI 634. CI R²(53) SCHs CI

600. CI R²(19) SCHs CI 635. CI R²(54) SCHs CI

601 . CI R²(20) SCHs CI 636. CI R²(55) SCHs CI

602. CI R²(21 ) SCHs CI 637. CI R²(56) SCHs CI

603. CI R²(22) SCHs CI 638. CI R²(57) SCHs CI

604. CI R²(23) SCHs CI 639. CI R²(58) SCHs CI

605. CI R²(24) SCHs CI 640. CI R²(59) SCHs CI No. R¹ R² R³ R⁵ No. R¹ R² R³ R⁵

641 . CI R²(60) SCHs CI 676. CI R²(12) S (0)₂CHs F

642. CI R²(61 ) SCHs CI 677. CI R²(13) S (0)₂CHs F

643. CI R²(62) SCHs CI 678. CI R²(14) s (0)₂CHs F

644. CI R²(63) SCHs CI 679. CI R²(15) s (0)₂CHs F

645. CI R²(64) SCHs CI 680. CI R²(16) s (0)₂CHs F

646. CI R²(65) SCHs CI 681 . CI R²(17) s (0)₂CHs F

647. CI R²(66) SCHs CI 682. CI R²(18) s (0)₂CHs F

648. CI R²(67) SCHs CI 683. CI R²(19) s (0)₂CHs F

649. CI R²(68) SCHs CI 684. CI R²(20) s (0)₂CHs F

650. CI R²(69) SCHs CI 685. CI R²(21 ) s (0)₂CHs F

651 . CI R²(70) SCHs CI 686. CI R²(22) s (0)₂CHs F

652. CI R²(71 ) SCHs CI 687. CI R²(23) s (0)₂CHs F

653. CI R²(72) SCHs CI 688. CI R²(24) s (0)₂CHs F

654. CI R²(73) SCHs CI 689. CI R²(25) s (0)₂CHs F

655. CI R²(74) SCHs CI 690. CI R²(26) s (0)₂CHs F

656. CI R²(75) SCHs CI 691 . CI R²(27) s (0)₂CHs F

657. CI R²(76) SCHs CI 692. CI R²(28) s (0)₂CHs F

658. CI R²(77) SCHs CI 693. CI R²(29) s (0)₂CHs F

659. CI R²(78) SCHs CI 694. CI R²(30) s (0)₂CHs F

660. CI R²(79) SCHs CI 695. CI R²(31 ) s (0)₂CHs F

661 . CI R²(80) SCHs CI 696. CI R²(32) s (0)₂CHs F

662. CI R²(81 ) SCHs CI 697. CI R²(33) s (0)₂CHs F

663. CI R²(82) SCHs CI 698. CI R²(34) s (0)₂CHs F

664. CI R²(83) SCHs CI 699. CI R²(35) s (0)₂CHs F

665. CI R²(1 ) S(0)₂CHs F 700. CI R²(36) s (0)₂CHs F

666. CI R²(2) S(0)₂CHs F 701 . CI R²(37) s (0)₂CHs F

667. CI R²(3) S(0)₂CHs F 702. CI R²(38) s (0)₂CHs F

668. CI R²(4) S(0)₂CHs F 703. CI R²(39) s (0)₂CHs F

669. CI R²(5) S(0)₂CHs F 704. CI R²(40) s (0)₂CHs F

670. CI R²(6) S(0)₂CHs F 705. CI R²(41 ) s (0)₂CHs F

671 . CI R²(7) S(0)₂CHs F 706. CI R²(42) s (0)₂CHs F

672. CI R²(8) S(0)₂CHs F 707. CI R²(43) s (0)₂CHs F

673. CI R²(9) S(0)₂CHs F 708. CI R²(44) s (0)₂CHs F

674. CI R²(10) S(0)₂CHs F 709. CI R²(45) s (0)₂CHs F

675. CI R²(1 1 ) S(0)₂CHs F 710. CI R²(46) s (0)₂CHs F No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

71 1 . CI R2(47) S (0)₂CH₃ F 746. CI R²(82) S(0)₂CH₃ F

712. CI R²(48) S (0)₂CH₃ F 747. CI R²(83) S(0)₂CH₃ F

713. CI R²(49) s (0)₂CH₃ F 748. CI R²(1 ) S(0)₂CH₃ CI

714. CI R²(50) s (0)₂CH₃ F 749. CI R²(2) S(0)₂CH₃ CI

715. CI R²(51 ) s (0)₂CH₃ F 750. CI R²(3) S(0)₂CH₃ CI

716. CI R²(52) s (0)₂CH₃ F 751 . CI R²(4) S(0)₂CH₃ CI

717. CI R²(53) s (0)₂CH₃ F 752. CI R²(5) S(0)₂CH₃ CI

718. CI R²(54) s (0)₂CH₃ F 753. CI R²(6) S(0)₂CH₃ CI

719. CI R²(55) s (0)₂CH₃ F 754. CI R²(7) S(0)₂CH₃ CI

720. CI R²(56) s (0)₂CH₃ F 755. CI R²(8) S(0)₂CH₃ CI

721 . CI R²(57) s (0)₂CH₃ F 756. CI R²(9) S(0)₂CH₃ CI

722. CI R²(58) s (0)₂CH₃ F 757. CI R²(10) S(0)₂CH₃ CI

723. CI R²(59) s (0)₂CH₃ F 758. CI R2(1 1 ) S(0)₂CH₃ CI

724. CI R²(60) s (0)₂CH₃ F 759. CI R²(12) S(0)₂CH₃ CI

725. CI R²(61 ) s (0)₂CH₃ F 760. CI R²(13) S(0)₂CH₃ CI

726. CI R²(62) s (0)₂CH₃ F 761 . CI R²(14) S(0)₂CH₃ CI

727. CI R²(63) s (0)₂CH₃ F 762. CI R²(15) S(0)₂CH₃ CI

728. CI R²(64) s (0)₂CH₃ F 763. CI R²(16) S(0)₂CH₃ CI

729. CI R²(65) s (0)₂CH₃ F 764. CI R²(17) S(0)₂CH₃ CI

730. CI R²(66) s (0)₂CH₃ F 765. CI R²(18) S(0)₂CH₃ CI

731 . CI R²(67) s (0)₂CH₃ F 766. CI R²(19) S(0)₂CH₃ CI

732. CI R²(68) s (0)₂CH₃ F 767. CI R²(20) S(0)₂CH₃ CI

733. CI R²(69) s (0)₂CH₃ F 768. CI R²(21 ) S(0)₂CH₃ CI

734. CI R²(70) s (0)₂CH₃ F 769. CI R²(22) S(0)₂CH₃ CI

735. CI R²(71 ) s (0)₂CH₃ F 770. CI R²(23) S(0)₂CH₃ CI

736. CI R²(72) s (0)₂CH₃ F 771 . CI R²(24) S(0)₂CH₃ CI

737. CI R²(73) s (0)₂CH₃ F 772. CI R²(25) S(0)₂CH₃ CI

738. CI R²(74) s (0)₂CH₃ F 773. CI R²(26) S(0)₂CH₃ CI

739. CI R²(75) s (0)₂CH₃ F 774. CI R²(27) S(0)₂CH₃ CI

740. CI R²(76) s (0)₂CH₃ F 775. CI R²(28) S(0)₂CH₃ CI

741 . CI R²(77) s (0)₂CH₃ F 776. CI R²(29) S(0)₂CH₃ CI

742. CI R²(78) s (0)₂CH₃ F 777. CI R²(30) S(0)₂CH₃ CI

743. CI R²(79) s (0)₂CH₃ F 778. CI R²(31 ) S(0)₂CH₃ CI

744. CI R²(80) s (0)₂CH₃ F 779. CI R²(32) S(0)₂CH₃ CI

745. CI R²(81 ) s (0)₂CH₃ F 780. CI R²(33) S(0)₂CH₃ CI No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

781 . CI R²(34) S(0)₂CH₃ CI 816. CI R²(69) S(0)₂CH₃ CI

782. CI R²(35) S(0)₂CH₃ CI 817. CI R²(70) S(0)₂CH₃ CI

783. CI R²(36) S(0)₂CH₃ CI 818. CI R²(71 ) S(0)₂CH₃ CI

784. CI R²(37) S(0)₂CH₃ CI 819. CI R²(72) S(0)₂CH₃ CI

785. CI R²(38) S(0)₂CH₃ CI 820. CI R²(73) S(0)₂CH₃ CI

786. CI R²(39) S(0)₂CH₃ CI 821 . CI R²(74) S(0)₂CH₃ CI

787. CI R²(40) S(0)₂CH₃ CI 822. CI R²(75) S(0)₂CH₃ CI

788. CI R²(41 ) S(0)₂CH₃ CI 823. CI R²(76) S(0)₂CH₃ CI

789. CI R²(42) S(0)₂CH₃ CI 824. CI R²(77) S(0)₂CH₃ CI

790. CI R²(43) S(0)₂CH₃ CI 825. CI R²(78) S(0)₂CH₃ CI

791 . CI R²(44) S(0)₂CH₃ CI 826. CI R²(79) S(0)₂CH₃ CI

792. CI R²(45) S(0)₂CH₃ CI 827. CI R²(80) S(0)₂CH₃ CI

793. CI R²(46) S(0)₂CH₃ CI 828. CI R²(81 ) S(0)₂CH₃ CI

794. CI R²(47) S(0)₂CH₃ CI 829. CI R²(82) S(0)₂CH₃ CI

795. CI R²(48) S(0)₂CH₃ CI 830. CI R²(83) S(0)₂CH₃ CI

796. CI R²(49) S(0)₂CH₃ CI 831 . Br R²(1 ) CI F

797. CI R²(50) S(0)₂CH₃ CI 832. Br R²(2) CI F

798. CI R²(51 ) S(0)₂CH₃ CI 833. Br R²(3) CI F

799. CI R²(52) S(0)₂CH₃ CI 834. Br R²(4) CI F

800. CI R²(53) S(0)₂CH₃ CI 835. Br R²(5) CI F

801 . CI R²(54) S(0)₂CH₃ CI 836. Br R²(6) CI F

802. CI R²(55) S(0)₂CH₃ CI 837. Br R²(7) CI F

803. CI R²(56) S(0)₂CH₃ CI 838. Br R²(8) CI F

804. CI R²(57) S(0)₂CH₃ CI 839. Br R²(9) CI F

805. CI R²(58) S(0)₂CH₃ CI 840. Br R²(10) CI F

806. CI R²(59) S(0)₂CH₃ CI 841 . Br R2(1 1 ) CI F

807. CI R²(60) S(0)₂CH₃ CI 842. Br R²(12) CI F

808. CI R²(61 ) S(0)₂CH₃ CI 843. Br R²(13) CI F

809. CI R²(62) S(0)₂CH₃ CI 844. Br R²(14) CI F

810. CI R²(63) S(0)₂CH₃ CI 845. Br R²(15) CI F

81 1 . CI R²(64) S(0)₂CH₃ CI 846. Br R²(16) CI F

812. CI R²(65) S(0)₂CH₃ CI 847. Br R²(17) CI F

813. CI R²(66) S(0)₂CH₃ CI 848. Br R²(18) CI F

814. CI R²(67) S(0)₂CH₃ CI 849. Br R²(19) CI F

815. CI R²(68) S(0)₂CH₃ CI 850. Br R²(20) CI F No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

851 . Br R2(21 ) CI F 886. Br R2(56) CI F

852. Br R2(22) CI F 887. Br R2(57) CI F

853. Br R2(23) CI F 888. Br R2(58) CI F

854. Br R2(24) CI F 889. Br R2(59) CI F

855. Br R2(25) CI F 890. Br R2(60) CI F

856. Br R2(26) CI F 891 . Br R2(61 ) CI F

857. Br R2(27) CI F 892. Br R2(62) CI F

858. Br R2(28) CI F 893. Br R2(63) CI F

859. Br R2(29) CI F 894. Br R2(64) CI F

860. Br R2(30) CI F 895. Br R2(65) CI F

861 . Br R2(31 ) CI F 896. Br R2(66) CI F

862. Br R2(32) CI F 897. Br R2(67) CI F

863. Br R2(33) CI F 898. Br R2(68) CI F

864. Br R2(34) CI F 899. Br R2(69) CI F

865. Br R2(35) CI F 900. Br R2(70) CI F

866. Br R2(36) CI F 901 . Br R2(71 ) CI F

867. Br R2(37) CI F 902. Br R2(72) CI F

868. Br R2(38) CI F 903. Br R2(73) CI F

869. Br R2(39) CI F 904. Br R2(74) CI F

870. Br R2(40) CI F 905. Br R2(75) CI F

871 . Br R2(41 ) CI F 906. Br R2(76) CI F

872. Br R2(42) CI F 907. Br R2(77) CI F

873. Br R2(43) CI F 908. Br R2(78) CI F

874. Br R2(44) CI F 909. Br R2(79) CI F

875. Br R2(45) CI F 910. Br R2(80) CI F

876. Br R2(46) CI F 91 1 . Br R2(81 ) CI F

877. Br R2(47) CI F 912. Br R2(82) CI F

878. Br R2(48) CI F 913. Br R2(83) CI F

879. Br R2(49) CI F 914. Br R2(1 ) CI CI

880. Br R2(50) CI F 915. Br R2(2) CI CI

881 . Br R2(51 ) CI F 916. Br R2(3) CI CI

882. Br R2(52) CI F 917. Br R2(4) CI CI

883. Br R2(53) CI F 918. Br R2(5) CI CI

884. Br R2(54) CI F 919. Br R2(6) CI CI

885. Br R2(55) CI F 920. Br R2(7) CI CI No. R¹ R² R³ R⁵ No. R¹ R² R³ R⁵

921 . Br R2(8) CI CI 956. Br R2(43) CI CI

922. Br R2(9) CI CI 957. Br R2(44) CI CI

923. Br R2(10) CI CI 958. Br R2(45) CI CI

924. Br R2(1 1 ) CI CI 959. Br R2(46) CI CI

925. Br R2(12) CI CI 960. Br R2(47) CI CI

926. Br R2(13) CI CI 961 . Br R2(48) CI CI

927. Br R2(14) CI CI 962. Br R2(49) CI CI

928. Br R2(15) CI CI 963. Br R2(50) CI CI

929. Br R2(16) CI CI 964. Br R2(51 ) CI CI

930. Br R2(17) CI CI 965. Br R2(52) CI CI

931 . Br R2(18) CI CI 966. Br R2(53) CI CI

932. Br R2(19) CI CI 967. Br R2(54) CI CI

933. Br R2(20) CI CI 968. Br R2(55) CI CI

934. Br R2(21 ) CI CI 969. Br R2(56) CI CI

935. Br R2(22) CI CI 970. Br R2(57) CI CI

936. Br R2(23) CI CI 971 . Br R2(58) CI CI

937. Br R2(24) CI CI 972. Br R2(59) CI CI

938. Br R2(25) CI CI 973. Br R2(60) CI CI

939. Br R2(26) CI CI 974. Br R2(61 ) CI CI

940. Br R2(27) CI CI 975. Br R2(62) CI CI

941 . Br R2(28) CI CI 976. Br R2(63) CI CI

942. Br R2(29) CI CI 977. Br R2(64) CI CI

943. Br R2(30) CI CI 978. Br R2(65) CI CI

944. Br R2(31 ) CI CI 979. Br R2(66) CI CI

945. Br R2(32) CI CI 980. Br R2(67) CI CI

946. Br R2(33) CI CI 981 . Br R2(68) CI CI

947. Br R2(34) CI CI 982. Br R2(69) CI CI

948. Br R2(35) CI CI 983. Br R2(70) CI CI

949. Br R2(36) CI CI 984. Br R2(71 ) CI CI

950. Br R2(37) CI CI 985. Br R2(72) CI CI

951 . Br R2(38) CI CI 986. Br R2(73) CI CI

952. Br R2(39) CI CI 987. Br R2(74) CI CI

953. Br R2(40) CI CI 988. Br R2(75) CI CI

954. Br R2(41 ) CI CI 989. Br R2(76) CI CI

955. Br R2(42) CI CI 990. Br R2(77) CI CI No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

991 . Br R²(78) CI CI 1026. Br R²(30) Br F

992. Br R²(79) CI CI 1027. Br R²(31 ) Br F

993. Br R²(80) CI CI 1028. Br R²(32) Br F

994. Br R²(81 ) CI CI 1029. Br R²(33) Br F

995. Br R²(82) CI CI 1030. Br R²(34) Br F

996. Br R²(83) CI CI 1031 . Br R²(35) Br F

997. Br R²(1 ) Br F 1032. Br R²(36) Br F

998. Br R²(2) Br F 1033. Br R²(37) Br F

999. Br R²(3) Br F 1034. Br R²(38) Br F

1000. Br R²(4) Br F 1035. Br R²(39) Br F

1001 . Br R²(5) Br F 1036. Br R²(40) Br F

1002. Br R²(6) Br F 1037. Br R²(41 ) Br F

1003. Br R²(7) Br F 1038. Br R²(42) Br F

1004. Br R²(8) Br F 1039. Br R²(43) Br F

1005. Br R²(9) Br F 1040. Br R²(44) Br F

1006. Br R²(10) Br F 1041 . Br R²(45) Br F

1007. Br R²(1 1 ) Br F 1042. Br R²(46) Br F

1008. Br R²(12) Br F 1043. Br R²(47) Br F

1009. Br R²(13) Br F 1044. Br R²(48) Br F

1010. Br R²(14) Br F 1045. Br R²(49) Br F

101 1 . Br R²(15) Br F 1046. Br R²(50) Br F

1012. Br R²(16) Br F 1047. Br R²(51 ) Br F

1013. Br R²(17) Br F 1048. Br R²(52) Br F

1014. Br R²(18) Br F 1049. Br R²(53) Br F

1015. Br R²(19) Br F 1050. Br R²(54) Br F

1016. Br R²(20) Br F 1051 . Br R²(55) Br F

1017. Br R²(21 ) Br F 1052. Br R²(56) Br F

1018. Br R²(22) Br F 1053. Br R²(57) Br F

1019. Br R²(23) Br F 1054. Br R²(58) Br F

1020. Br R²(24) Br F 1055. Br R²(59) Br F

1021 . Br R²(25) Br F 1056. Br R²(60) Br F

1022. Br R²(26) Br F 1057. Br R²(61 ) Br F

1023. Br R²(27) Br F 1058. Br R²(62) Br F

1024. Br R²(28) Br F 1059. Br R²(63) Br F

1025. Br R²(29) Br F 1060. Br R²(64) Br F No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

1061. Br R²(65) Br F 1096. Br R²(17) Br CI

1062. Br R²(66) Br F 1097. Br R²(18) Br CI

1063. Br R²(67) Br F 1098. Br R²(19) Br CI

1064. Br R²(68) Br F 1099. Br R²(20) Br CI

1065. Br R²(69) Br F 1100. Br R²(21) Br CI

1066. Br R²(70) Br F 1101. Br R²(22) Br CI

1067. Br R²(71) Br F 1102. Br R²(23) Br CI

1068. Br R²(72) Br F 1103. Br R²(24) Br CI

1069. Br R²(73) Br F 1104. Br R²(25) Br CI

1070. Br R²(74) Br F 1105. Br R²(26) Br CI

1071. Br R²(75) Br F 1106. Br R²(27) Br CI

1072. Br R²(76) Br F 1107. Br R²(28) Br CI

1073. Br R²(77) Br F 1108. Br R²(29) Br CI

1074. Br R²(78) Br F 1109. Br R²(30) Br CI

1075. Br R²(79) Br F 1110. Br R²(31) Br CI

1076. Br R²(80) Br F 1111. Br R²(32) Br CI

1077. Br R²(81) Br F 1112. Br R²(33) Br CI

1078. Br R²(82) Br F 1113. Br R²(34) Br CI

1079. Br R²(83) Br F 1114. Br R²(35) Br CI

1080. Br R²(1) Br CI 1115. Br R²(36) Br CI

1081. Br R²(2) Br CI 1116. Br R²(37) Br CI

1082. Br R²(3) Br CI 1117. Br R²(38) Br CI

1083. Br R²(4) Br CI 1118. Br R²(39) Br CI

1084. Br R²(5) Br CI 1119. Br R²(40) Br CI

1085. Br R²(6) Br CI 1120. Br R²(41) Br CI

1086. Br R²(7) Br CI 1121. Br R²(42) Br CI

1087. Br R²(8) Br CI 1122. Br R²(43) Br CI

1088. Br R²(9) Br CI 1123. Br R²(44) Br CI

1089. Br R²(10) Br CI 1124. Br R²(45) Br CI

1090. Br R²(11) Br CI 1125. Br R²(46) Br CI

1091. Br R²(12) Br CI 1126. Br R²(47) Br CI

1092. Br R²(13) Br CI 1127. Br R²(48) Br CI

1093. Br R²(14) Br CI 1128. Br R²(49) Br CI

1094. Br R²(15) Br CI 1129. Br R²(50) Br CI

1095. Br R²(16) Br CI 1130. Br R²(51) Br CI No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

1131. Br R²(52) Br CI 1166. Br R²(4) CFs F

1132. Br R²(53) Br CI 1167. Br R²(5) CFs F

1133. Br R²(54) Br CI 1168. Br R²(6) CFs F

1134. Br R²(55) Br CI 1169. Br R²(7) CFs F

1135. Br R²(56) Br CI 1170. Br R²(8) CFs F

1136. Br R²(57) Br CI 1171. Br R²(9) CFs F

1137. Br R²(58) Br CI 1172. Br R²(10) CFs F

1138. Br R²(59) Br CI 1173. Br R2(11) CFs F

1139. Br R²(60) Br CI 1174. Br R²(12) CFs F

1140. Br R²(61) Br CI 1175. Br R²(13) CFs F

1141. Br R²(62) Br CI 1176. Br R²(14) CFs F

1142. Br R²(63) Br CI 1177. Br R²(15) CFs F

1143. Br R²(64) Br CI 1178. Br R²(16) CFs F

1144. Br R²(65) Br CI 1179. Br R²(17) CFs F

1145. Br R²(66) Br CI 1180. Br R²(18) CFs F

1146. Br R²(67) Br CI 1181. Br R²(19) CFs F

1147. Br R²(68) Br CI 1182. Br R²(20) CFs F

1148. Br R²(69) Br CI 1183. Br R²(21) CFs F

1149. Br R²(70) Br CI 1184. Br R²(22) CFs F

1150. Br R²(71) Br CI 1185. Br R²(23) CFs F

1151. Br R²(72) Br CI 1186. Br R²(24) CFs F

1152. Br R²(73) Br CI 1187. Br R²(25) CFs F

1153. Br R²(74) Br CI 1188. Br R²(26) CFs F

1154. Br R²(75) Br CI 1189. Br R²(27) CFs F

1155. Br R²(76) Br CI 1190. Br R²(28) CFs F

1156. Br R²(77) Br CI 1191. Br R²(29) CFs F

1157. Br R²(78) Br CI 1192. Br R²(30) CFs F

1158. Br R²(79) Br CI 1193. Br R²(31) CFs F

1159. Br R²(80) Br CI 1194. Br R²(32) CFs F

1160. Br R²(81) Br CI 1195. Br R²(33) CFs F

1161. Br R²(82) Br CI 1196. Br R²(34) CFs F

1162. Br R²(83) Br CI 1197. Br R²(35) CFs F

1163. Br R²(1) CFs F 1198. Br R²(36) CFs F

1164. Br R²(2) CFs F 1199. Br R²(37) CFs F

1165. Br R²(3) CFs F 1200. Br R²(38) CFs F No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

1201 . Br R²(39) CFs F 1236. Br R²(74) CFs F

1202. Br R²(40) CFs F 1237. Br R²(75) CFs F

1203. Br R2(41 ) CFs F 1238. Br R²(76) CFs F

1204. Br R2(42) CFs F 1239. Br R²(77) CFs F

1205. Br R²(43) CFs F 1240. Br R²(78) CFs F

1206. Br R2(44) CFs F 1241 . Br R²(79) CFs F

1207. Br R²(45) CFs F 1242. Br R²(80) CFs F

1208. Br R²(46) CFs F 1243. Br R²(81 ) CFs F

1209. Br R²(47) CFs F 1244. Br R²(82) CFs F

1210. Br R²(48) CFs F 1245. Br R²(83) CFs F

121 1 . Br R²(49) CFs F 1246. Br R²(1 ) CFs CI

1212. Br R²(50) CFs F 1247. Br R²(2) CFs CI

1213. Br R²(51 ) CFs F 1248. Br R²(3) CFs CI

1214. Br R²(52) CFs F 1249. Br R²(4) CFs CI

1215. Br R²(53) CFs F 1250. Br R²(5) CFs CI

1216. Br R²(54) CFs F 1251 . Br R²(6) CFs CI

1217. Br R²(55) CFs F 1252. Br R²(7) CFs CI

1218. Br R²(56) CFs F 1253. Br R²(8) CFs CI

1219. Br R²(57) CFs F 1254. Br R²(9) CFs CI

1220. Br R²(58) CFs F 1255. Br R²(10) CFs CI

1221 . Br R²(59) CFs F 1256. Br R2(1 1 ) CFs CI

1222. Br R²(60) CFs F 1257. Br R²(12) CFs CI

1223. Br R²(61 ) CFs F 1258. Br R²(13) CFs CI

1224. Br R²(62) CFs F 1259. Br R²(14) CFs CI

1225. Br R²(63) CFs F 1260. Br R²(15) CFs CI

1226. Br R²(64) CFs F 1261 . Br R²(16) CFs CI

1227. Br R²(65) CFs F 1262. Br R²(17) CFs CI

1228. Br R²(66) CFs F 1263. Br R²(18) CFs CI

1229. Br R²(67) CFs F 1264. Br R²(19) CFs CI

1230. Br R²(68) CFs F 1265. Br R²(20) CFs CI

1231 . Br R²(69) CFs F 1266. Br R²(21 ) CFs CI

1232. Br R²(70) CFs F 1267. Br R²(22) CFs CI

1233. Br R²(71 ) CFs F 1268. Br R²(23) CFs CI

1234. Br R²(72) CFs F 1269. Br R²(24) CFs CI

1235. Br R²(73) CFs F 1270. Br R²(25) CFs CI No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

1271 . Br R²(26) CFs CI 1306. Br R²(61 ) CFs CI

1272. Br R2(27) CFs CI 1307. Br R²(62) CFs CI

1273. Br R²(28) CFs CI 1308. Br R²(63) CFs CI

1274. Br R²(29) CFs CI 1309. Br R²(64) CFs CI

1275. Br R²(30) CFs CI 1310. Br R²(65) CFs CI

1276. Br R²(31 ) CFs CI 131 1 . Br R²(66) CFs CI

1277. Br R²(32) CFs CI 1312. Br R²(67) CFs CI

1278. Br R²(33) CFs CI 1313. Br R²(68) CFs CI

1279. Br R²(34) CFs CI 1314. Br R²(69) CFs CI

1280. Br R²(35) CFs CI 1315. Br R²(70) CFs CI

1281 . Br R²(36) CFs CI 1316. Br R²(71 ) CFs CI

1282. Br R²(37) CFs CI 1317. Br R²(72) CFs CI

1283. Br R²(38) CFs CI 1318. Br R²(73) CFs CI

1284. Br R²(39) CFs CI 1319. Br R²(74) CFs CI

1285. Br R²(40) CFs CI 1320. Br R²(75) CFs CI

1286. Br R²(41 ) CFs CI 1321 . Br R²(76) CFs CI

1287. Br R²(42) CFs CI 1322. Br R²(77) CFs CI

1288. Br R²(43) CFs CI 1323. Br R²(78) CFs CI

1289. Br R²(44) CFs CI 1324. Br R²(79) CFs CI

1290. Br R²(45) CFs CI 1325. Br R²(80) CFs CI

1291 . Br R²(46) CFs CI 1326. Br R²(81 ) CFs CI

1292. Br R²(47) CFs CI 1327. Br R²(82) CFs CI

1293. Br R²(48) CFs CI 1328. Br R²(83) CFs CI

1294. Br R²(49) CFs CI 1329. Br R²(1 ) SCHs F

1295. Br R²(50) CFs CI 1330. Br R²(2) SCHs F

1296. Br R²(51 ) CFs CI 1331 . Br R²(3) SCHs F

1297. Br R²(52) CFs CI 1332. Br R²(4) SCHs F

1298. Br R²(53) CFs CI 1333. Br R²(5) SCHs F

1299. Br R²(54) CFs CI 1334. Br R²(6) SCHs F

1300. Br R²(55) CFs CI 1335. Br R²(7) SCHs F

1301 . Br R²(56) CFs CI 1336. Br R²(8) SCHs F

1302. Br R²(57) CFs CI 1337. Br R²(9) SCHs F

1303. Br R²(58) CFs CI 1338. Br R²(10) SCHs F

1304. Br R²(59) CFs CI 1339. Br R2(1 1 ) SCHs F

1305. Br R²(60) CFs CI 1340. Br R²(12) SCHs F No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

1341 . Br R²(13) SCHs F 1376. Br R²(48) SCHs F

1342. Br R2(14) SCHs F 1377. Br R²(49) SCHs F

1343. Br R²(15) SCHs F 1378. Br R²(50) SCHs F

1344. Br R²(16) SCHs F 1379. Br R²(51 ) SCHs F

1345. Br R2(17) SCHs F 1380. Br R²(52) SCHs F

1346. Br R²(18) SCHs F 1381 . Br R²(53) SCHs F

1347. Br R²(19) SCHs F 1382. Br R²(54) SCHs F

1348. Br R²(20) SCHs F 1383. Br R²(55) SCHs F

1349. Br R²(21 ) SCHs F 1384. Br R²(56) SCHs F

1350. Br R²(22) SCHs F 1385. Br R²(57) SCHs F

1351 . Br R²(23) SCHs F 1386. Br R²(58) SCHs F

1352. Br R²(24) SCHs F 1387. Br R²(59) SCHs F

1353. Br R²(25) SCHs F 1388. Br R²(60) SCHs F

1354. Br R²(26) SCHs F 1389. Br R²(61 ) SCHs F

1355. Br R²(27) SCHs F 1390. Br R²(62) SCHs F

1356. Br R²(28) SCHs F 1391 . Br R²(63) SCHs F

1357. Br R²(29) SCHs F 1392. Br R²(64) SCHs F

1358. Br R²(30) SCHs F 1393. Br R²(65) SCHs F

1359. Br R²(31 ) SCHs F 1394. Br R²(66) SCHs F

1360. Br R²(32) SCHs F 1395. Br R²(67) SCHs F

1361 . Br R²(33) SCHs F 1396. Br R²(68) SCHs F

1362. Br R²(34) SCHs F 1397. Br R²(69) SCHs F

1363. Br R²(35) SCHs F 1398. Br R²(70) SCHs F

1364. Br R²(36) SCHs F 1399. Br R²(71 ) SCHs F

1365. Br R²(37) SCHs F 1400. Br R²(72) SCHs F

1366. Br R²(38) SCHs F 1401 . Br R²(73) SCHs F

1367. Br R²(39) SCHs F 1402. Br R²(74) SCHs F

1368. Br R²(40) SCHs F 1403. Br R²(75) SCHs F

1369. Br R²(41 ) SCHs F 1404. Br R²(76) SCHs F

1370. Br R²(42) SCHs F 1405. Br R²(77) SCHs F

1371 . Br R²(43) SCHs F 1406. Br R²(78) SCHs F

1372. Br R²(44) SCHs F 1407. Br R²(79) SCHs F

1373. Br R²(45) SCHs F 1408. Br R²(80) SCHs F

1374. Br R²(46) SCHs F 1409. Br R²(81 ) SCHs F

1375. Br R²(47) SCHs F 1410. Br R²(82) SCHs F No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

141 1 . Br R²(83) SCHs F 1446. Br R2(35) SCHs CI

1412. Br R2(1 ) SCHs CI 1447. Br R2(36) SCHs CI

1413. Br R2(2) SCHs CI 1448. Br R2(37) SCHs CI

1414. Br R2(3) SCHs CI 1449. Br R2(38) SCHs CI

1415. Br R2(4) SCHs CI 1450. Br R2(39) SCHs CI

1416. Br R2(5) SCHs CI 1451 . Br R2(40) SCHs CI

1417. Br R2(6) SCHs CI 1452. Br R2(41 ) SCHs CI

1418. Br R2(7) SCHs CI 1453. Br R2(42) SCHs CI

1419. Br R2(8) SCHs CI 1454. Br R2(43) SCHs CI

1420. Br R2(9) SCHs CI 1455. Br R2(44) SCHs CI

1421 . Br R2(10) SCHs CI 1456. Br R2(45) SCHs CI

1422. Br R2(1 1 ) SCHs CI 1457. Br R2(46) SCHs CI

1423. Br R2(12) SCHs CI 1458. Br R2(47) SCHs CI

1424. Br R2(13) SCHs CI 1459. Br R2(48) SCHs CI

1425. Br R2(14) SCHs CI 1460. Br R2(49) SCHs CI

1426. Br R2(15) SCHs CI 1461 . Br R2(50) SCHs CI

1427. Br R2(16) SCHs CI 1462. Br R2(51 ) SCHs CI

1428. Br R2(17) SCHs CI 1463. Br R2(52) SCHs CI

1429. Br R2(18) SCHs CI 1464. Br R2(53) SCHs CI

1430. Br R2(19) SCHs CI 1465. Br R2(54) SCHs CI

1431 . Br R2(20) SCHs CI 1466. Br R2(55) SCHs CI

1432. Br R2(21 ) SCHs CI 1467. Br R2(56) SCHs CI

1433. Br R2(22) SCHs CI 1468. Br R2(57) SCHs CI

1434. Br R2(23) SCHs CI 1469. Br R2(58) SCHs CI

1435. Br R2(24) SCHs CI 1470. Br R2(59) SCHs CI

1436. Br R2(25) SCHs CI 1471 . Br R2(60) SCHs CI

1437. Br R2(26) SCHs CI 1472. Br R2(61 ) SCHs CI

1438. Br R2(27) SCHs CI 1473. Br R2(62) SCHs CI

1439. Br R2(28) SCHs CI 1474. Br R2(63) SCHs CI

1440. Br R2(29) SCHs CI 1475. Br R2(64) SCHs CI

1441 . Br R2(30) SCHs CI 1476. Br R2(65) SCHs CI

1442. Br R2(31 ) SCHs CI 1477. Br R2(66) SCHs CI

1443. Br R2(32) SCHs CI 1478. Br R2(67) SCHs CI

1444. Br R2(33) SCHs CI 1479. Br R2(68) SCHs CI

1445. Br R2(34) SCHs CI 1480. Br R2(69) SCHs CI No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

1481 . Br R²(70) SCHs CI 1516. Br R²(22) S (0)₂CHs F

1482. Br R2(71 ) SCHs CI 1517. Br R²(23) S (0)₂CHs F

1483. Br R2(72) SCHs CI 1518. Br R²(24) s (0)₂CHs F

1484. Br R²(73) SCHs CI 1519. Br R²(25) s (0)₂CHs F

1485. Br R2(74) SCHs CI 1520. Br R²(26) s (0)₂CHs F

1486. Br R²(75) SCHs CI 1521 . Br R²(27) s (0)₂CHs F

1487. Br R²(76) SCHs CI 1522. Br R²(28) s (0)₂CHs F

1488. Br R2(77) SCHs CI 1523. Br R²(29) s (0)₂CHs F

1489. Br R²(78) SCHs CI 1524. Br R²(30) s (0)₂CHs F

1490. Br R²(79) SCHs CI 1525. Br R²(31 ) s (0)₂CHs F

1491 . Br R²(80) SCHs CI 1526. Br R²(32) s (0)₂CHs F

1492. Br R²(81 ) SCHs CI 1527. Br R²(33) s (0)₂CHs F

1493. Br R²(82) SCHs CI 1528. Br R²(34) s (0)₂CHs F

1494. Br R²(83) SCHs CI 1529. Br R²(35) s (0)₂CHs F

1495. Br R²(1 ) S(0)₂CHs F 1530. Br R²(36) s (0)₂CHs F

1496. Br R²(2) S(0)₂CHs F 1531 . Br R²(37) s (0)₂CHs F

1497. Br R²(3) S(0)₂CHs F 1532. Br R²(38) s (0)₂CHs F

1498. Br R²(4) S(0)₂CHs F 1533. Br R²(39) s (0)₂CHs F

1499. Br R²(5) S(0)₂CHs F 1534. Br R²(40) s (0)₂CHs F

1500. Br R²(6) S(0)₂CHs F 1535. Br R²(41 ) s (0)₂CHs F

1501 . Br R²(7) S(0)₂CHs F 1536. Br R²(42) s (0)₂CHs F

1502. Br R²(8) S(0)₂CHs F 1537. Br R²(43) s (0)₂CHs F

1503. Br R²(9) S(0)₂CHs F 1538. Br R²(44) s (0)₂CHs F

1504. Br R²(10) S(0)₂CHs F 1539. Br R²(45) s (0)₂CHs F

1505. Br R²(1 1 ) S(0)₂CHs F 1540. Br R²(46) s (0)₂CHs F

1506. Br R²(12) S(0)₂CHs F 1541 . Br R²(47) s (0)₂CHs F

1507. Br R²(13) S(0)₂CHs F 1542. Br R²(48) s (0)₂CHs F

1508. Br R²(14) S(0)₂CHs F 1543. Br R²(49) s (0)₂CHs F

1509. Br R²(15) S(0)₂CHs F 1544. Br R²(50) s (0)₂CHs F

1510. Br R²(16) S(0)₂CHs F 1545. Br R²(51 ) s (0)₂CHs F

151 1 . Br R²(17) S(0)₂CHs F 1546. Br R²(52) s (0)₂CHs F

1512. Br R²(18) S(0)₂CHs F 1547. Br R²(53) s (0)₂CHs F

1513. Br R²(19) S(0)₂CHs F 1548. Br R²(54) s (0)₂CHs F

1514. Br R²(20) S(0)₂CHs F 1549. Br R²(55) s (0)₂CHs F

1515. Br R²(21 ) S(0)₂CHs F 1550. Br R²(56) s (0)₂CHs F No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

1551. Br R²(57) S(0)₂CH₃ F 1586. Br R²(9) S(0)₂CH₃ CI

1552. Br R²(58) S(0)₂CH₃ F 1587. Br R²(10) S(0)₂CH₃ CI

1553. Br R²(59) S(0)₂CH₃ F 1588. Br R2(1 1 ) S(0)₂CH₃ CI

1554. Br R²(60) S(0)₂CH₃ F 1589. Br R²(12) S(0)₂CH₃ CI

1555. Br R²(61 ) S(0)₂CH₃ F 1590. Br R²(13) S(0)₂CH₃ CI

1556. Br R²(62) S(0)₂CH₃ F 1591. Br R²(14) S(0)₂CH₃ CI

1557. Br R²(63) S(0)₂CH₃ F 1592. Br R²(15) S(0)₂CH₃ CI

1558. Br R²(64) S(0)₂CH₃ F 1593. Br R²(16) S(0)₂CH₃ CI

1559. Br R²(65) S(0)₂CH₃ F 1594. Br R²(17) S(0)₂CH₃ CI

1560. Br R²(66) S(0)₂CH₃ F 1595. Br R²(18) S(0)₂CH₃ CI

1561. Br R²(67) S(0)₂CH₃ F 1596. Br R²(19) S(0)₂CH₃ CI

1562. Br R²(68) S(0)₂CH₃ F 1597. Br R²(20) S(0)₂CH₃ CI

1563. Br R²(69) S(0)₂CH₃ F 1598. Br R²(21 ) S(0)₂CH₃ CI

1564. Br R²(70) S(0)₂CH₃ F 1599. Br R²(22) S(0)₂CH₃ CI

1565. Br R²(71 ) S(0)₂CH₃ F 1600. Br R²(23) S(0)₂CH₃ CI

1566. Br R²(72) S(0)₂CH₃ F 1601. Br R²(24) S(0)₂CH₃ CI

1567. Br R²(73) S(0)₂CH₃ F 1602. Br R²(25) S(0)₂CH₃ CI

1568. Br R²(74) S(0)₂CH₃ F 1603. Br R²(26) S(0)₂CH₃ CI

1569. Br R²(75) S(0)₂CH₃ F 1604. Br R²(27) S(0)₂CH₃ CI

1570. Br R²(76) S(0)₂CH₃ F 1605. Br R²(28) S(0)₂CH₃ CI

1571. Br R²(77) S(0)₂CH₃ F 1606. Br R²(29) S(0)₂CH₃ CI

1572. Br R²(78) S(0)₂CH₃ F 1607. Br R²(30) S(0)₂CH₃ CI

1573. Br R²(79) S(0)₂CH₃ F 1608. Br R²(31 ) S(0)₂CH₃ CI

1574. Br R²(80) S(0)₂CH₃ F 1609. Br R²(32) S(0)₂CH₃ CI

1575. Br R²(81 ) S(0)₂CH₃ F 1610. Br R²(33) S(0)₂CH₃ CI

1576. Br R²(82) S(0)₂CH₃ F 161 1. Br R²(34) S(0)₂CH₃ CI

1577. Br R²(83) S(0)₂CH₃ F 1612. Br R²(35) S(0)₂CH₃ CI

1578. Br R²(1 ) S(0)₂CH₃ CI 1613. Br R²(36) S(0)₂CH₃ CI

1579. Br R²(2) S(0)₂CH₃ CI 1614. Br R²(37) S(0)₂CH₃ CI

1580. Br R²(3) S(0)₂CH₃ CI 1615. Br R²(38) S(0)₂CH₃ CI

1581. Br R²(4) S(0)₂CH₃ CI 1616. Br R²(39) S(0)₂CH₃ CI

1582. Br R²(5) S(0)₂CH₃ CI 1617. Br R²(40) S(0)₂CH₃ CI

1583. Br R²(6) S(0)₂CH₃ CI 1618. Br R²(41 ) S(0)₂CH₃ CI

1584. Br R²(7) S(0)₂CH₃ CI 1619. Br R²(42) S(0)₂CH₃ CI

1585. Br R²(8) S(0)₂CH₃ CI 1620. Br R²(43) S(0)₂CH₃ CI No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

1621 . Br R2(44) S(0)₂CH₃ CI 1656. Br R²(79) S(0)₂CH₃ CI

1622. Br R²(45) S(0)₂CH₃ CI 1657. Br R²(80) S(0)₂CH₃ CI

1623. Br R²(46) S(0)₂CH₃ CI 1658. Br R²(81 ) S(0)₂CH₃ CI

1624. Br R2(47) S(0)₂CH₃ CI 1659. Br R²(82) S(0)₂CH₃ CI

1625. Br R²(48) S(0)₂CH₃ CI 1660. Br R²(83) S(0)₂CH₃ CI

1626. Br R²(49) S(0)₂CH₃ CI 1661 . CH₃ R²(1 ) CI F

1627. Br R²(50) S(0)₂CH₃ CI 1662. CH₃ R²(2) CI F

1628. Br R²(51 ) S(0)₂CH₃ CI 1663. CH₃ R²(3) CI F

1629. Br R²(52) S(0)₂CH₃ CI 1664. CH₃ R²(4) CI F

1630. Br R²(53) S(0)₂CH₃ CI 1665. CH₃ R²(5) CI F

1631 . Br R²(54) S(0)₂CH₃ CI 1666. CH₃ R²(6) CI F

1632. Br R²(55) S(0)₂CH₃ CI 1667. CH₃ R²(7) CI F

1633. Br R²(56) S(0)₂CH₃ CI 1668. CH₃ R²(8) CI F

1634. Br R²(57) S(0)₂CH₃ CI 1669. CH₃ R²(9) CI F

1635. Br R²(58) S(0)₂CH₃ CI 1670. CH₃ R²(10) CI F

1636. Br R²(59) S(0)₂CH₃ CI 1671 . CH₃ R2(1 1 ) CI F

1637. Br R²(60) S(0)₂CH₃ CI 1672. CH₃ R²(12) CI F

1638. Br R²(61 ) S(0)₂CH₃ CI 1673. CH₃ R²(13) CI F

1639. Br R²(62) S(0)₂CH₃ CI 1674. CH₃ R²(14) CI F

1640. Br R²(63) S(0)₂CH₃ CI 1675. CH₃ R²(15) CI F

1641 . Br R²(64) S(0)₂CH₃ CI 1676. CH₃ R²(16) CI F

1642. Br R²(65) S(0)₂CH₃ CI 1677. CH₃ R²(17) CI F

1643. Br R²(66) S(0)₂CH₃ CI 1678. CH₃ R²(18) CI F

1644. Br R²(67) S(0)₂CH₃ CI 1679. CH₃ R²(19) CI F

1645. Br R²(68) S(0)₂CH₃ CI 1680. CH₃ R²(20) CI F

1646. Br R²(69) S(0)₂CH₃ CI 1681 . CH₃ R²(21 ) CI F

1647. Br R²(70) S(0)₂CH₃ CI 1682. CH₃ R²(22) CI F

1648. Br R²(71 ) S(0)₂CH₃ CI 1683. CH₃ R²(23) CI F

1649. Br R²(72) S(0)₂CH₃ CI 1684. CH₃ R²(24) CI F

1650. Br R²(73) S(0)₂CH₃ CI 1685. CH₃ R²(25) CI F

1651 . Br R²(74) S(0)₂CH₃ CI 1686. CH₃ R²(26) CI F

1652. Br R²(75) S(0)₂CH₃ CI 1687. CH₃ R²(27) CI F

1653. Br R²(76) S(0)₂CH₃ CI 1688. CH₃ R²(28) CI F

1654. Br R²(77) S(0)₂CH₃ CI 1689. CH₃ R²(29) CI F

1655. Br R²(78) S(0)₂CH₃ CI 1690. CH₃ R²(30) CI F No. R¹ R² R³ R⁵ No. R¹ R² R³ R⁵

1691 . CHs R²(31 ) CI F 1726. CHs R²(66) CI F

1692. CHs R²(32) CI F 1727. CHs R²(67) CI F

1693. CHs R²(33) CI F 1728. CHs R²(68) CI F

1694. CHs R²(34) CI F 1729. CHs R²(69) CI F

1695. CHs R²(35) CI F 1730. CHs R²(70) CI F

1696. CHs R²(36) CI F 1731 . CHs R²(71 ) CI F

1697. CHs R²(37) CI F 1732. CHs R²(72) CI F

1698. CHs R²(38) CI F 1733. CHs R²(73) CI F

1699. CHs R²(39) CI F 1734. CHs R²(74) CI F

1700. CHs R²(40) CI F 1735. CHs R²(75) CI F

1701 . CHs R²(41 ) CI F 1736. CHs R²(76) CI F

1702. CHs R²(42) CI F 1737. CHs R²(77) CI F

1703. CHs R²(43) CI F 1738. CHs R²(78) CI F

1704. CHs R²(44) CI F 1739. CHs R²(79) CI F

1705. CHs R²(45) CI F 1740. CHs R²(80) CI F

1706. CHs R²(46) CI F 1741 . CHs R²(81 ) CI F

1707. CHs R²(47) CI F 1742. CHs R²(82) CI F

1708. CHs R²(48) CI F 1743. CHs R²(83) CI F

1709. CHs R²(49) CI F 1744. CHs R²(1 ) CI CI

1710. CHs R²(50) CI F 1745. CHs R²(2) CI CI

171 1 . CHs R²(51 ) CI F 1746. CHs R²(3) CI CI

1712. CHs R²(52) CI F 1747. CHs R²(4) CI CI

1713. CHs R²(53) CI F 1748. CHs R²(5) CI CI

1714. CHs R²(54) CI F 1749. CHs R²(6) CI CI

1715. CHs R²(55) CI F 1750. CHs R²(7) CI CI

1716. CHs R²(56) CI F 1751 . CHs R²(8) CI CI

1717. CHs R²(57) CI F 1752. CHs R²(9) CI CI

1718. CHs R²(58) CI F 1753. CHs R²(10) CI CI

1719. CHs R²(59) CI F 1754. CHs R2(1 1 ) CI CI

1720. CHs R²(60) CI F 1755. CHs R²(12) CI CI

1721 . CHs R²(61 ) CI F 1756. CHs R²(13) CI CI

1722. CHs R²(62) CI F 1757. CHs R²(14) CI CI

1723. CHs R²(63) CI F 1758. CHs R²(15) CI CI

1724. CHs R²(64) CI F 1759. CHs R²(16) CI CI

1725. CHs R²(65) CI F 1760. CHs R²(17) CI CI No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

1761 . CHs R²(18) CI CI 1796. CHs R²(53) CI CI

1762. CHs R²(19) CI CI 1797. CHs R²(54) CI CI

1763. CHs R²(20) CI CI 1798. CHs R²(55) CI CI

1764. CHs R²(21 ) CI CI 1799. CHs R²(56) CI CI

1765. CHs R²(22) CI CI 1800. CHs R²(57) CI CI

1766. CHs R²(23) CI CI 1801 . CHs R²(58) CI CI

1767. CHs R²(24) CI CI 1802. CHs R²(59) CI CI

1768. CHs R²(25) CI CI 1803. CHs R²(60) CI CI

1769. CHs R²(26) CI CI 1804. CHs R²(61 ) CI CI

1770. CHs R²(27) CI CI 1805. CHs R²(62) CI CI

1771 . CHs R²(28) CI CI 1806. CHs R²(63) CI CI

1772. CHs R²(29) CI CI 1807. CHs R²(64) CI CI

1773. CHs R²(30) CI CI 1808. CHs R²(65) CI CI

1774. CHs R²(31 ) CI CI 1809. CHs R²(66) CI CI

1775. CHs R²(32) CI CI 1810. CHs R²(67) CI CI

1776. CHs R²(33) CI CI 181 1 . CHs R²(68) CI CI

1777. CHs R²(34) CI CI 1812. CHs R²(69) CI CI

1778. CHs R²(35) CI CI 1813. CHs R²(70) CI CI

1779. CHs R²(36) CI CI 1814. CHs R²(71 ) CI CI

1780. CHs R²(37) CI CI 1815. CHs R²(72) CI CI

1781 . CHs R²(38) CI CI 1816. CHs R²(73) CI CI

1782. CHs R²(39) CI CI 1817. CHs R²(74) CI CI

1783. CHs R²(40) CI CI 1818. CHs R²(75) CI CI

1784. CHs R²(41 ) CI CI 1819. CHs R²(76) CI CI

1785. CHs R²(42) CI CI 1820. CHs R²(77) CI CI

1786. CHs R²(43) CI CI 1821 . CHs R²(78) CI CI

1787. CHs R²(44) CI CI 1822. CHs R²(79) CI CI

1788. CHs R²(45) CI CI 1823. CHs R²(80) CI CI

1789. CHs R²(46) CI CI 1824. CHs R²(81 ) CI CI

1790. CHs R²(47) CI CI 1825. CHs R²(82) CI CI

1791 . CHs R²(48) CI CI 1826. CHs R²(83) CI CI

1792. CHs R²(49) CI CI 1827. CHs R²(1 ) Br F

1793. CHs R²(50) CI CI 1828. CHs R²(2) Br F

1794. CHs R²(51 ) CI CI 1829. CHs R²(3) Br F

1795. CHs R²(52) CI CI 1830. CHs R²(4) Br F No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

1831 . CHs R2(5) Br F 1866. CHs R2(40) Br F

1832. CHs R2(6) Br F 1867. CHs R2(41 ) Br F

1833. CHs R2(7) Br F 1868. CHs R2(42) Br F

1834. CHs R2(8) Br F 1869. CHs R2(43) Br F

1835. CHs R2(9) Br F 1870. CHs R2(44) Br F

1836. CHs R2(10) Br F 1871 . CHs R2(45) Br F

1837. CHs R2(1 1 ) Br F 1872. CHs R2(46) Br F

1838. CHs R2(12) Br F 1873. CHs R2(47) Br F

1839. CHs R2(13) Br F 1874. CHs R2(48) Br F

1840. CHs R2(14) Br F 1875. CHs R2(49) Br F

1841 . CHs R2(15) Br F 1876. CHs R2(50) Br F

1842. CHs R2(16) Br F 1877. CHs R2(51 ) Br F

1843. CHs R2(17) Br F 1878. CHs R2(52) Br F

1844. CHs R2(18) Br F 1879. CHs R2(53) Br F

1845. CHs R2(19) Br F 1880. CHs R2(54) Br F

1846. CHs R2(20) Br F 1881 . CHs R2(55) Br F

1847. CHs R2(21 ) Br F 1882. CHs R2(56) Br F

1848. CHs R2(22) Br F 1883. CHs R2(57) Br F

1849. CHs R2(23) Br F 1884. CHs R2(58) Br F

1850. CHs R2(24) Br F 1885. CHs R2(59) Br F

1851 . CHs R2(25) Br F 1886. CHs R2(60) Br F

1852. CHs R2(26) Br F 1887. CHs R2(61 ) Br F

1853. CHs R2(27) Br F 1888. CHs R2(62) Br F

1854. CHs R2(28) Br F 1889. CHs R2(63) Br F

1855. CHs R2(29) Br F 1890. CHs R2(64) Br F

1856. CHs R2(30) Br F 1891 . CHs R2(65) Br F

1857. CHs R2(31 ) Br F 1892. CHs R2(66) Br F

1858. CHs R2(32) Br F 1893. CHs R2(67) Br F

1859. CHs R2(33) Br F 1894. CHs R2(68) Br F

1860. CHs R2(34) Br F 1895. CHs R2(69) Br F

1861 . CHs R2(35) Br F 1896. CHs R2(70) Br F

1862. CHs R2(36) Br F 1897. CHs R2(71 ) Br F

1863. CHs R2(37) Br F 1898. CHs R2(72) Br F

1864. CHs R2(38) Br F 1899. CHs R2(73) Br F

1865. CHs R2(39) Br F 1900. CHs R2(74) Br F No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

1901 . CHs R²(75) Br F 1936. CHs R²(27) Br CI

1902. CHs R²(76) Br F 1937. CHs R²(28) Br CI

1903. CHs R2(77) Br F 1938. CHs R²(29) Br CI

1904. CHs R²(78) Br F 1939. CHs R²(30) Br CI

1905. CHs R²(79) Br F 1940. CHs R²(31 ) Br CI

1906. CHs R²(80) Br F 1941 . CHs R²(32) Br CI

1907. CHs R²(81 ) Br F 1942. CHs R²(33) Br CI

1908. CHs R²(82) Br F 1943. CHs R²(34) Br CI

1909. CHs R²(83) Br F 1944. CHs R²(35) Br CI

1910. CHs R²(1 ) Br CI 1945. CHs R²(36) Br CI

191 1 . CHs R²(2) Br CI 1946. CHs R²(37) Br CI

1912. CHs R²(3) Br CI 1947. CHs R²(38) Br CI

1913. CHs R²(4) Br CI 1948. CHs R²(39) Br CI

1914. CHs R²(5) Br CI 1949. CHs R²(40) Br CI

1915. CHs R²(6) Br CI 1950. CHs R²(41 ) Br CI

1916. CHs R²(7) Br CI 1951 . CHs R²(42) Br CI

1917. CHs R²(8) Br CI 1952. CHs R²(43) Br CI

1918. CHs R²(9) Br CI 1953. CHs R²(44) Br CI

1919. CHs R²(10) Br CI 1954. CHs R²(45) Br CI

1920. CHs R²(1 1 ) Br CI 1955. CHs R²(46) Br CI

1921 . CHs R²(12) Br CI 1956. CHs R²(47) Br CI

1922. CHs R²(13) Br CI 1957. CHs R²(48) Br CI

1923. CHs R²(14) Br CI 1958. CHs R²(49) Br CI

1924. CHs R²(15) Br CI 1959. CHs R²(50) Br CI

1925. CHs R²(16) Br CI 1960. CHs R²(51 ) Br CI

1926. CHs R²(17) Br CI 1961 . CHs R²(52) Br CI

1927. CHs R²(18) Br CI 1962. CHs R²(53) Br CI

1928. CHs R²(19) Br CI 1963. CHs R²(54) Br CI

1929. CHs R²(20) Br CI 1964. CHs R²(55) Br CI

1930. CHs R²(21 ) Br CI 1965. CHs R²(56) Br CI

1931 . CHs R²(22) Br CI 1966. CHs R²(57) Br CI

1932. CHs R²(23) Br CI 1967. CHs R²(58) Br CI

1933. CHs R²(24) Br CI 1968. CHs R²(59) Br CI

1934. CHs R²(25) Br CI 1969. CHs R²(60) Br CI

1935. CHs R²(26) Br CI 1970. CHs R²(61 ) Br CI No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

1971 . CHs R²(62) Br CI 2006. CHs R²(14) CFs F

1972. CHs R²(63) Br CI 2007. CHs R²(15) CFs F

1973. CHs R²(64) Br CI 2008. CHs R²(16) CFs F

1974. CHs R²(65) Br CI 2009. CHs R²(17) CFs F

1975. CHs R²(66) Br CI 2010. CHs R²(18) CFs F

1976. CHs R²(67) Br CI 201 1 . CHs R²(19) CFs F

1977. CHs R²(68) Br CI 2012. CHs R²(20) CFs F

1978. CHs R²(69) Br CI 2013. CHs R²(21 ) CFs F

1979. CHs R²(70) Br CI 2014. CHs R²(22) CFs F

1980. CHs R²(71 ) Br CI 2015. CHs R²(23) CFs F

1981 . CHs R²(72) Br CI 2016. CHs R²(24) CFs F

1982. CHs R²(73) Br CI 2017. CHs R²(25) CFs F

1983. CHs R²(74) Br CI 2018. CHs R²(26) CFs F

1984. CHs R²(75) Br CI 2019. CHs R²(27) CFs F

1985. CHs R²(76) Br CI 2020. CHs R²(28) CFs F

1986. CHs R²(77) Br CI 2021 . CHs R²(29) CFs F

1987. CHs R²(78) Br CI 2022. CHs R²(30) CFs F

1988. CHs R²(79) Br CI 2023. CHs R²(31 ) CFs F

1989. CHs R²(80) Br CI 2024. CHs R²(32) CFs F

1990. CHs R²(81 ) Br CI 2025. CHs R²(33) CFs F

1991 . CHs R²(82) Br CI 2026. CHs R²(34) CFs F

1992. CHs R²(83) Br CI 2027. CHs R²(35) CFs F

1993. CHs R²(1 ) CFs F 2028. CHs R²(36) CFs F

1994. CHs R²(2) CFs F 2029. CHs R²(37) CFs F

1995. CHs R²(3) CFs F 2030. CHs R²(38) CFs F

1996. CHs R²(4) CFs F 2031 . CHs R²(39) CFs F

1997. CHs R²(5) CFs F 2032. CHs R²(40) CFs F

1998. CHs R²(6) CFs F 2033. CHs R²(41 ) CFs F

1999. CHs R²(7) CFs F 2034. CHs R²(42) CFs F

2000. CHs R²(8) CFs F 2035. CHs R²(43) CFs F

2001 . CHs R²(9) CFs F 2036. CHs R²(44) CFs F

2002. CHs R²(10) CFs F 2037. CHs R²(45) CFs F

2003. CHs R²(1 1 ) CFs F 2038. CHs R²(46) CFs F

2004. CHs R²(12) CFs F 2039. CHs R²(47) CFs F

2005. CHs R²(13) CFs F 2040. CHs R²(48) CFs F No. R¹ R² R³ R⁵ No. R¹ R² R³ R⁵

2041 . CHs R²(49) CFs F 2076. CHs R²(1 ) CFs CI

2042. CHs R²(50) CFs F 2077. CHs R²(2) CFs CI

2043. CHs R²(51 ) CFs F 2078. CHs R²(3) CFs CI

2044. CHs R²(52) CFs F 2079. CHs R²(4) CFs CI

2045. CHs R²(53) CFs F 2080. CHs R²(5) CFs CI

2046. CHs R²(54) CFs F 2081 . CHs R²(6) CFs CI

2047. CHs R²(55) CFs F 2082. CHs R²(7) CFs CI

2048. CHs R²(56) CFs F 2083. CHs R²(8) CFs CI

2049. CHs R²(57) CFs F 2084. CHs R²(9) CFs CI

2050. CHs R²(58) CFs F 2085. CHs R²(10) CFs CI

2051 . CHs R²(59) CFs F 2086. CHs R2(1 1 ) CFs CI

2052. CHs R²(60) CFs F 2087. CHs R²(12) CFs CI

2053. CHs R²(61 ) CFs F 2088. CHs R²(13) CFs CI

2054. CHs R²(62) CFs F 2089. CHs R²(14) CFs CI

2055. CHs R²(63) CFs F 2090. CHs R²(15) CFs CI

2056. CHs R²(64) CFs F 2091 . CHs R²(16) CFs CI

2057. CHs R²(65) CFs F 2092. CHs R²(17) CFs CI

2058. CHs R²(66) CFs F 2093. CHs R²(18) CFs CI

2059. CHs R²(67) CFs F 2094. CHs R²(19) CFs CI

2060. CHs R²(68) CFs F 2095. CHs R²(20) CFs CI

2061 . CHs R²(69) CFs F 2096. CHs R²(21 ) CFs CI

2062. CHs R²(70) CFs F 2097. CHs R²(22) CFs CI

2063. CHs R²(71 ) CFs F 2098. CHs R²(23) CFs CI

2064. CHs R²(72) CFs F 2099. CHs R²(24) CFs CI

2065. CHs R²(73) CFs F 2100. CHs R²(25) CFs CI

2066. CHs R²(74) CFs F 2101 . CHs R²(26) CFs CI

2067. CHs R²(75) CFs F 2102. CHs R²(27) CFs CI

2068. CHs R²(76) CFs F 2103. CHs R²(28) CFs CI

2069. CHs R²(77) CFs F 2104. CHs R²(29) CFs CI

2070. CHs R²(78) CFs F 2105. CHs R²(30) CFs CI

2071 . CHs R²(79) CFs F 2106. CHs R²(31 ) CFs CI

2072. CHs R²(80) CFs F 2107. CHs R²(32) CFs CI

2073. CHs R²(81 ) CFs F 2108. CHs R²(33) CFs CI

2074. CHs R²(82) CFs F 2109. CHs R²(34) CFs CI

2075. CHs R²(83) CFs F 21 10. CHs R²(35) CFs CI No. R¹ R² R³ R⁵ No. R¹ R² R³ R⁵

21 1 1 . CHs R²(36) CFs CI 2146. CHs R²(71 ) CFs CI

21 12. CHs R²(37) CFs CI 2147. CHs R²(72) CFs CI

21 13. CHs R²(38) CFs CI 2148. CHs R²(73) CFs CI

21 14. CHs R²(39) CFs CI 2149. CHs R²(74) CFs CI

21 15. CHs R²(40) CFs CI 2150. CHs R²(75) CFs CI

21 16. CHs R²(41 ) CFs CI 2151 . CHs R²(76) CFs CI

21 17. CHs R²(42) CFs CI 2152. CHs R²(77) CFs CI

21 18. CHs R²(43) CFs CI 2153. CHs R²(78) CFs CI

21 19. CHs R²(44) CFs CI 2154. CHs R²(79) CFs CI

2120. CHs R²(45) CFs CI 2155. CHs R²(80) CFs CI

2121 . CHs R²(46) CFs CI 2156. CHs R²(81 ) CFs CI

2122. CHs R²(47) CFs CI 2157. CHs R²(82) CFs CI

2123. CHs R²(48) CFs CI 2158. CHs R²(83) CFs CI

2124. CHs R²(49) CFs CI 2159. CHs R²(1 ) SCHs F

2125. CHs R²(50) CFs CI 2160. CHs R²(2) SCHs F

2126. CHs R²(51 ) CFs CI 2161 . CHs R²(3) SCHs F

2127. CHs R²(52) CFs CI 2162. CHs R²(4) SCHs F

2128. CHs R²(53) CFs CI 2163. CHs R²(5) SCHs F

2129. CHs R²(54) CFs CI 2164. CHs R²(6) SCHs F

2130. CHs R²(55) CFs CI 2165. CHs R²(7) SCHs F

2131 . CHs R²(56) CFs CI 2166. CHs R²(8) SCHs F

2132. CHs R²(57) CFs CI 2167. CHs R²(9) SCHs F

2133. CHs R²(58) CFs CI 2168. CHs R²(10) SCHs F

2134. CHs R²(59) CFs CI 2169. CHs R2(1 1 ) SCHs F

2135. CHs R²(60) CFs CI 2170. CHs R²(12) SCHs F

2136. CHs R²(61 ) CFs CI 2171 . CHs R²(13) SCHs F

2137. CHs R²(62) CFs CI 2172. CHs R²(14) SCHs F

2138. CHs R²(63) CFs CI 2173. CHs R²(15) SCHs F

2139. CHs R²(64) CFs CI 2174. CHs R²(16) SCHs F

2140. CHs R²(65) CFs CI 2175. CHs R²(17) SCHs F

2141 . CHs R²(66) CFs CI 2176. CHs R²(18) SCHs F

2142. CHs R²(67) CFs CI 2177. CHs R²(19) SCHs F

2143. CHs R²(68) CFs CI 2178. CHs R²(20) SCHs F

2144. CHs R²(69) CFs CI 2179. CHs R²(21 ) SCHs F

2145. CHs R²(70) CFs CI 2180. CHs R²(22) SCHs F No. R¹ R² R³ R⁵ No. R¹ R² R³ R⁵

2181 . CHs R²(23) SCHs F 2216. CHs R²(58) SCHs F

2182. CHs R2(24) SCHs F 2217. CHs R²(59) SCHs F

2183. CHs R²(25) SCHs F 2218. CHs R²(60) SCHs F

2184. CHs R²(26) SCHs F 2219. CHs R²(61 ) SCHs F

2185. CHs R2(27) SCHs F 2220. CHs R²(62) SCHs F

2186. CHs R²(28) SCHs F 2221 . CHs R²(63) SCHs F

2187. CHs R²(29) SCHs F 2222. CHs R²(64) SCHs F

2188. CHs R²(30) SCHs F 2223. CHs R²(65) SCHs F

2189. CHs R²(31 ) SCHs F 2224. CHs R²(66) SCHs F

2190. CHs R²(32) SCHs F 2225. CHs R²(67) SCHs F

2191 . CHs R²(33) SCHs F 2226. CHs R²(68) SCHs F

2192. CHs R²(34) SCHs F 2227. CHs R²(69) SCHs F

2193. CHs R²(35) SCHs F 2228. CHs R²(70) SCHs F

2194. CHs R²(36) SCHs F 2229. CHs R²(71 ) SCHs F

2195. CHs R²(37) SCHs F 2230. CHs R²(72) SCHs F

2196. CHs R²(38) SCHs F 2231 . CHs R²(73) SCHs F

2197. CHs R²(39) SCHs F 2232. CHs R²(74) SCHs F

2198. CHs R²(40) SCHs F 2233. CHs R²(75) SCHs F

2199. CHs R²(41 ) SCHs F 2234. CHs R²(76) SCHs F

2200. CHs R²(42) SCHs F 2235. CHs R²(77) SCHs F

2201 . CHs R²(43) SCHs F 2236. CHs R²(78) SCHs F

2202. CHs R²(44) SCHs F 2237. CHs R²(79) SCHs F

2203. CHs R²(45) SCHs F 2238. CHs R²(80) SCHs F

2204. CHs R²(46) SCHs F 2239. CHs R²(81 ) SCHs F

2205. CHs R²(47) SCHs F 2240. CHs R²(82) SCHs F

2206. CHs R²(48) SCHs F 2241 . CHs R²(83) SCHs F

2207. CHs R²(49) SCHs F 2242. CHs R²(1 ) SCHs CI

2208. CHs R²(50) SCHs F 2243. CHs R²(2) SCHs CI

2209. CHs R²(51 ) SCHs F 2244. CHs R²(3) SCHs CI

2210. CHs R²(52) SCHs F 2245. CHs R²(4) SCHs CI

221 1 . CHs R²(53) SCHs F 2246. CHs R²(5) SCHs CI

2212. CHs R²(54) SCHs F 2247. CHs R²(6) SCHs CI

2213. CHs R²(55) SCHs F 2248. CHs R²(7) SCHs CI

2214. CHs R²(56) SCHs F 2249. CHs R²(8) SCHs CI

2215. CHs R²(57) SCHs F 2250. CHs R²(9) SCHs CI No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

2251 . CHs R²(10) SCHs CI 2286. CHs R²(45) SCHs CI

2252. CHs R2(1 1 ) SCHs CI 2287. CHs R²(46) SCHs CI

2253. CHs R2(12) SCHs CI 2288. CHs R²(47) SCHs CI

2254. CHs R²(13) SCHs CI 2289. CHs R²(48) SCHs CI

2255. CHs R2(14) SCHs CI 2290. CHs R²(49) SCHs CI

2256. CHs R²(15) SCHs CI 2291 . CHs R²(50) SCHs CI

2257. CHs R²(16) SCHs CI 2292. CHs R²(51 ) SCHs CI

2258. CHs R²(17) SCHs CI 2293. CHs R²(52) SCHs CI

2259. CHs R²(18) SCHs CI 2294. CHs R²(53) SCHs CI

2260. CHs R²(19) SCHs CI 2295. CHs R²(54) SCHs CI

2261 . CHs R²(20) SCHs CI 2296. CHs R²(55) SCHs CI

2262. CHs R²(21 ) SCHs CI 2297. CHs R²(56) SCHs CI

2263. CHs R²(22) SCHs CI 2298. CHs R²(57) SCHs CI

2264. CHs R²(23) SCHs CI 2299. CHs R²(58) SCHs CI

2265. CHs R²(24) SCHs CI 2300. CHs R²(59) SCHs CI

2266. CHs R²(25) SCHs CI 2301 . CHs R²(60) SCHs CI

2267. CHs R²(26) SCHs CI 2302. CHs R²(61 ) SCHs CI

2268. CHs R²(27) SCHs CI 2303. CHs R²(62) SCHs CI

2269. CHs R²(28) SCHs CI 2304. CHs R²(63) SCHs CI

2270. CHs R²(29) SCHs CI 2305. CHs R²(64) SCHs CI

2271 . CHs R²(30) SCHs CI 2306. CHs R²(65) SCHs CI

2272. CHs R²(31 ) SCHs CI 2307. CHs R²(66) SCHs CI

2273. CHs R²(32) SCHs CI 2308. CHs R²(67) SCHs CI

2274. CHs R²(33) SCHs CI 2309. CHs R²(68) SCHs CI

2275. CHs R²(34) SCHs CI 2310. CHs R²(69) SCHs CI

2276. CHs R²(35) SCHs CI 231 1 . CHs R²(70) SCHs CI

2277. CHs R²(36) SCHs CI 2312. CHs R²(71 ) SCHs CI

2278. CHs R²(37) SCHs CI 2313. CHs R²(72) SCHs CI

2279. CHs R²(38) SCHs CI 2314. CHs R²(73) SCHs CI

2280. CHs R²(39) SCHs CI 2315. CHs R²(74) SCHs CI

2281 . CHs R²(40) SCHs CI 2316. CHs R²(75) SCHs CI

2282. CHs R²(41 ) SCHs CI 2317. CHs R²(76) SCHs CI

2283. CHs R²(42) SCHs CI 2318. CHs R²(77) SCHs CI

2284. CHs R²(43) SCHs CI 2319. CHs R²(78) SCHs CI

2285. CHs R²(44) SCHs CI 2320. CHs R²(79) SCHs CI No. R¹ R² R³ R⁵ No. R¹ R² R³ R⁵

2321 . CHs R²(80) SCHs CI 2356. CHs R²(32) S (0)₂CHs F

2322. CHs R²(81 ) SCHs CI 2357. CHs R²(33) S (0)₂CHs F

2323. CHs R²(82) SCHs CI 2358. CHs R²(34) s (0)₂CHs F

2324. CHs R²(83) SCHs CI 2359. CHs R²(35) s (0)₂CHs F

2325. CHs R²(1 ) S(0)₂CHs F 2360. CHs R²(36) s (0)₂CHs F

2326. CHs R²(2) S(0)₂CHs F 2361 . CHs R²(37) s (0)₂CHs F

2327. CHs R²(3) S(0)₂CHs F 2362. CHs R²(38) s (0)₂CHs F

2328. CHs R²(4) S(0)₂CHs F 2363. CHs R²(39) s (0)₂CHs F

2329. CHs R²(5) S(0)₂CHs F 2364. CHs R²(40) s (0)₂CHs F

2330. CHs R²(6) S(0)₂CHs F 2365. CHs R²(41 ) s (0)₂CHs F

2331 . CHs R²(7) S(0)₂CHs F 2366. CHs R²(42) s (0)₂CHs F

2332. CHs R²(8) S(0)₂CHs F 2367. CHs R²(43) s (0)₂CHs F

2333. CHs R²(9) S(0)₂CHs F 2368. CHs R²(44) s (0)₂CHs F

2334. CHs R²(10) S(0)₂CHs F 2369. CHs R²(45) s (0)₂CHs F

2335. CHs R²(1 1 ) S(0)₂CHs F 2370. CHs R²(46) s (0)₂CHs F

2336. CHs R²(12) S(0)₂CHs F 2371 . CHs R²(47) s (0)₂CHs F

2337. CHs R²(13) S(0)₂CHs F 2372. CHs R²(48) s (0)₂CHs F

2338. CHs R²(14) S(0)₂CHs F 2373. CHs R²(49) s (0)₂CHs F

2339. CHs R²(15) S(0)₂CHs F 2374. CHs R²(50) s (0)₂CHs F

2340. CHs R²(16) S(0)₂CHs F 2375. CHs R²(51 ) s (0)₂CHs F

2341 . CHs R²(17) S(0)₂CHs F 2376. CHs R²(52) s (0)₂CHs F

2342. CHs R²(18) S(0)₂CHs F 2377. CHs R²(53) s (0)₂CHs F

2343. CHs R²(19) S(0)₂CHs F 2378. CHs R²(54) s (0)₂CHs F

2344. CHs R²(20) S(0)₂CHs F 2379. CHs R²(55) s (0)₂CHs F

2345. CHs R²(21 ) S(0)₂CHs F 2380. CHs R²(56) s (0)₂CHs F

2346. CHs R²(22) S(0)₂CHs F 2381 . CHs R²(57) s (0)₂CHs F

2347. CHs R²(23) S(0)₂CHs F 2382. CHs R²(58) s (0)₂CHs F

2348. CHs R²(24) S(0)₂CHs F 2383. CHs R²(59) s (0)₂CHs F

2349. CHs R²(25) S(0)₂CHs F 2384. CHs R²(60) s (0)₂CHs F

2350. CHs R²(26) S(0)₂CHs F 2385. CHs R²(61 ) s (0)₂CHs F

2351 . CHs R²(27) S(0)₂CHs F 2386. CHs R²(62) s (0)₂CHs F

2352. CHs R²(28) S(0)₂CHs F 2387. CHs R²(63) s (0)₂CHs F

2353. CHs R²(29) S(0)₂CHs F 2388. CHs R²(64) s (0)₂CHs F

2354. CHs R²(30) S(0)₂CHs F 2389. CHs R²(65) s (0)₂CHs F

2355. CHs R²(31 ) S(0)₂CHs F 2390. CHs R²(66) s (0)₂CHs F No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

2391 . CHs R²(67) S(0)₂CHs F 2426. CHs R²(19) S(0)₂CHs CI

2392. CHs R²(68) S(0)₂CHs F 2427. CHs R²(20) S(0)₂CHs CI

2393. CHs R²(69) S(0)₂CHs F 2428. CHs R²(21 ) S(0)₂CHs CI

2394. CHs R²(70) S(0)₂CHs F 2429. CHs R²(22) S(0)₂CHs CI

2395. CHs R²(71 ) S(0)₂CHs F 2430. CHs R²(23) S(0)₂CHs CI

2396. CHs R²(72) S(0)₂CHs F 2431 . CHs R²(24) S(0)₂CHs CI

2397. CHs R²(73) S(0)₂CHs F 2432. CHs R²(25) S(0)₂CHs CI

2398. CHs R²(74) S(0)₂CHs F 2433. CHs R²(26) S(0)₂CHs CI

2399. CHs R²(75) S(0)₂CHs F 2434. CHs R²(27) S(0)₂CHs CI

2400. CHs R²(76) S(0)₂CHs F 2435. CHs R²(28) S(0)₂CHs CI

2401 . CHs R²(77) S(0)₂CHs F 2436. CHs R²(29) S(0)₂CHs CI

2402. CHs R²(78) S(0)₂CHs F 2437. CHs R²(30) S(0)₂CHs CI

2403. CHs R²(79) S(0)₂CHs F 2438. CHs R²(31 ) S(0)₂CHs CI

2404. CHs R²(80) S(0)₂CHs F 2439. CHs R²(32) S(0)₂CHs CI

2405. CHs R²(81 ) S(0)₂CHs F 2440. CHs R²(33) S(0)₂CHs CI

2406. CHs R²(82) S(0)₂CHs F 2441 . CHs R²(34) S(0)₂CHs CI

2407. CHs R²(83) S(0)₂CHs F 2442. CHs R²(35) S(0)₂CHs CI

2408. CHs R²(1 ) S(0)₂CHs CI 2443. CHs R²(36) S(0)₂CHs CI

2409. CHs R²(2) S(0)₂CHs CI 2444. CHs R²(37) S(0)₂CHs CI

2410. CHs R²(3) S(0)₂CHs CI 2445. CHs R²(38) S(0)₂CHs CI

241 1 . CHs R²(4) S(0)₂CHs CI 2446. CHs R²(39) S(0)₂CHs CI

2412. CHs R²(5) S(0)₂CHs CI 2447. CHs R²(40) S(0)₂CHs CI

2413. CHs R²(6) S(0)₂CHs CI 2448. CHs R²(41 ) S(0)₂CHs CI

2414. CHs R²(7) S(0)₂CHs CI 2449. CHs R²(42) S(0)₂CHs CI

2415. CHs R²(8) S(0)₂CHs CI 2450. CHs R²(43) S(0)₂CHs CI

2416. CHs R²(9) S(0)₂CHs CI 2451 . CHs R²(44) S(0)₂CHs CI

2417. CHs R²(10) S(0)₂CHs CI 2452. CHs R²(45) S(0)₂CHs CI

2418. CHs R²(1 1 ) S(0)₂CHs CI 2453. CHs R²(46) S(0)₂CHs CI

2419. CHs R²(12) S(0)₂CHs CI 2454. CHs R²(47) S(0)₂CHs CI

2420. CHs R²(13) S(0)₂CHs CI 2455. CHs R²(48) S(0)₂CHs CI

2421 . CHs R²(14) S(0)₂CHs CI 2456. CHs R²(49) S(0)₂CHs CI

2422. CHs R²(15) S(0)₂CHs CI 2457. CHs R²(50) S(0)₂CHs CI

2423. CHs R²(16) S(0)₂CHs CI 2458. CHs R²(51 ) S(0)₂CHs CI

2424. CHs R²(17) S(0)₂CHs CI 2459. CHs R²(52) S(0)₂CHs CI

2425. CHs R²(18) S(0)₂CHs CI 2460. CHs R²(53) S(0)₂CHs CI No. R¹ R² R³ R⁵ No. R¹ R² R³ R⁵

2461 . CHs R²(54) S(0)₂CHs CI 2496. CI R²(6) I F

2462. CHs R²(55) S(0)₂CHs CI 2497. CI R²(7) I F

2463. CHs R²(56) S(0)₂CHs CI 2498. CI R²(8) I F

2464. CHs R²(57) S(0)₂CHs CI 2499. CI R²(9) I F

2465. CHs R²(58) S(0)₂CHs CI 2500. CI R²(10) I F

2466. CHs R²(59) S(0)₂CHs CI 2501 . CI R2(1 1 ) I F

2467. CHs R²(60) S(0)₂CHs CI 2502. CI R²(12) I F

2468. CHs R²(61 ) S(0)₂CHs CI 2503. CI R²(13) I F

2469. CHs R²(62) S(0)₂CHs CI 2504. CI R²(14) I F

2470. CHs R²(63) S(0)₂CHs CI 2505. CI R²(15) I F

2471 . CHs R²(64) S(0)₂CHs CI 2506. CI R²(16) I F

2472. CHs R²(65) S(0)₂CHs CI 2507. CI R²(17) I F

2473. CHs R²(66) S(0)₂CHs CI 2508. CI R²(18) I F

2474. CHs R²(67) S(0)₂CHs CI 2509. CI R²(19) I F

2475. CHs R²(68) S(0)₂CHs CI 2510. CI R²(20) I F

2476. CHs R²(69) S(0)₂CHs CI 251 1 . CI R²(21 ) I F

2477. CHs R²(70) S(0)₂CHs CI 2512. CI R²(22) I F

2478. CHs R²(71 ) S(0)₂CHs CI 2513. CI R²(23) I F

2479. CHs R²(72) S(0)₂CHs CI 2514. CI R²(24) I F

2480. CHs R²(73) S(0)₂CHs CI 2515. CI R²(25) I F

2481 . CHs R²(74) S(0)₂CHs CI 2516. CI R²(26) I F

2482. CHs R²(75) S(0)₂CHs CI 2517. CI R²(27) I F

2483. CHs R²(76) S(0)₂CHs CI 2518. CI R²(28) I F

2484. CHs R²(77) S(0)₂CHs CI 2519. CI R²(29) I F

2485. CHs R²(78) S(0)₂CHs CI 2520. CI R²(30) I F

2486. CHs R²(79) S(0)₂CHs CI 2521 . CI R²(31 ) I F

2487. CHs R²(80) S(0)₂CHs CI 2522. CI R²(32) I F

2488. CHs R²(81 ) S(0)₂CHs CI 2523. CI R²(33) I F

2489. CHs R²(82) S(0)₂CHs CI 2524. CI R²(34) I F

2490. CHs R²(83) S(0)₂CHs CI 2525. CI R²(35) I F

2491 . CI R²(1 ) I F 2526. CI R²(36) I F

2492. CI R²(2) I F 2527. CI R²(37) I F

2493. CI R²(3) I F 2528. CI R²(38) I F

2494. CI R²(4) I F 2529. CI R²(39) I F

2495. CI R²(5) I F 2530. CI R²(40) I F No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

2531 . CI R2(41 ) I F 2566. CI R2(76) I F

2532. CI R2(42) I F 2567. CI R2(77) I F

2533. CI R2(43) I F 2568. CI R2(78) I F

2534. CI R2(44) I F 2569. CI R2(79) I F

2535. CI R2(45) I F 2570. CI R2(80) I F

2536. CI R2(46) I F 2571 . CI R2(81 ) I F

2537. CI R2(47) I F 2572. CI R2(82) I F

2538. CI R2(48) I F 2573. CI R2(83) I F

2539. CI R2(49) I F 2574. CI R2(1 ) I CI

2540. CI R2(50) I F 2575. CI R2(2) I CI

2541 . CI R2(51 ) I F 2576. CI R2(3) I CI

2542. CI R2(52) I F 2577. CI R2(4) I CI

2543. CI R2(53) I F 2578. CI R2(5) I CI

2544. CI R2(54) I F 2579. CI R2(6) I CI

2545. CI R2(55) I F 2580. CI R2(7) I CI

2546. CI R2(56) I F 2581 . CI R2(8) I CI

2547. CI R2(57) I F 2582. CI R2(9) I CI

2548. CI R2(58) I F 2583. CI R2(10) I CI

2549. CI R2(59) I F 2584. CI R2(1 1 ) I CI

2550. CI R2(60) I F 2585. CI R2(12) I CI

2551 . CI R2(61 ) I F 2586. CI R2(13) I CI

2552. CI R2(62) I F 2587. CI R2(14) I CI

2553. CI R2(63) I F 2588. CI R2(15) I CI

2554. CI R2(64) I F 2589. CI R2(16) I CI

2555. CI R2(65) I F 2590. CI R2(17) I CI

2556. CI R2(66) I F 2591 . CI R2(18) I CI

2557. CI R2(67) I F 2592. CI R2(19) I CI

2558. CI R2(68) I F 2593. CI R2(20) I CI

2559. CI R2(69) I F 2594. CI R2(21 ) I CI

2560. CI R2(70) I F 2595. CI R2(22) I CI

2561 . CI R2(71 ) I F 2596. CI R2(23) I CI

2562. CI R2(72) I F 2597. CI R2(24) I CI

2563. CI R2(73) I F 2598. CI R2(25) I CI

2564. CI R2(74) I F 2599. CI R2(26) I CI

2565. CI R2(75) I F 2600. CI R2(27) I CI No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

2601 . CI R²(28) I CI 2636. CI R²(63) I CI

2602. CI R²(29) I CI 2637. CI R²(64) I CI

2603. CI R²(30) I CI 2638. CI R²(65) I CI

2604. CI R²(31 ) I CI 2639. CI R²(66) I CI

2605. CI R²(32) I CI 2640. CI R²(67) I CI

2606. CI R²(33) I CI 2641 . CI R²(68) I CI

2607. CI R²(34) I CI 2642. CI R²(69) I CI

2608. CI R²(35) I CI 2643. CI R²(70) I CI

2609. CI R²(36) I CI 2644. CI R²(71 ) I CI

2610. CI R²(37) I CI 2645. CI R²(72) I CI

261 1 . CI R²(38) I CI 2646. CI R²(73) I CI

2612. CI R²(39) I CI 2647. CI R²(74) I CI

2613. CI R²(40) I CI 2648. CI R²(75) I CI

2614. CI R²(41 ) I CI 2649. CI R²(76) I CI

2615. CI R²(42) I CI 2650. CI R²(77) I CI

2616. CI R²(43) I CI 2651 . CI R²(78) I CI

2617. CI R²(44) I CI 2652. CI R²(79) I CI

2618. CI R²(45) I CI 2653. CI R²(80) I CI

2619. CI R²(46) I CI 2654. CI R²(81 ) I CI

2620. CI R²(47) I CI 2655. CI R²(82) I CI

2621 . CI R²(48) I CI 2656. CI R²(83) I CI

2622. CI R²(49) I CI 2657. Br R²(1 ) I F

2623. CI R²(50) I CI 2658. Br R²(2) I F

2624. CI R²(51 ) I CI 2659. Br R²(3) I F

2625. CI R²(52) I CI 2660. Br R²(4) I F

2626. CI R²(53) I CI 2661 . Br R²(5) I F

2627. CI R²(54) I CI 2662. Br R²(6) I F

2628. CI R²(55) I CI 2663. Br R²(7) I F

2629. CI R²(56) I CI 2664. Br R²(8) I F

2630. CI R²(57) I CI 2665. Br R²(9) I F

2631 . CI R²(58) I CI 2666. Br R²(10) I F

2632. CI R²(59) I CI 2667. Br R2(1 1 ) I F

2633. CI R²(60) I CI 2668. Br R²(12) I F

2634. CI R²(61 ) I CI 2669. Br R²(13) I F

2635. CI R²(62) I CI 2670. Br R²(14) I F No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

2671 . Br R²(15) I F 2706. Br R²(50) I F

2672. Br R²(16) I F 2707. Br R²(51 ) I F

2673. Br R2(17) I F 2708. Br R²(52) I F

2674. Br R²(18) I F 2709. Br R²(53) I F

2675. Br R²(19) I F 2710. Br R²(54) I F

2676. Br R²(20) I F 271 1 . Br R²(55) I F

2677. Br R²(21 ) I F 2712. Br R²(56) I F

2678. Br R²(22) I F 2713. Br R²(57) I F

2679. Br R²(23) I F 2714. Br R²(58) I F

2680. Br R²(24) I F 2715. Br R²(59) I F

2681 . Br R²(25) I F 2716. Br R²(60) I F

2682. Br R²(26) I F 2717. Br R²(61 ) I F

2683. Br R²(27) I F 2718. Br R²(62) I F

2684. Br R²(28) I F 2719. Br R²(63) I F

2685. Br R²(29) I F 2720. Br R²(64) I F

2686. Br R²(30) I F 2721 . Br R²(65) I F

2687. Br R²(31 ) I F 2722. Br R²(66) I F

2688. Br R²(32) I F 2723. Br R²(67) I F

2689. Br R²(33) I F 2724. Br R²(68) I F

2690. Br R²(34) I F 2725. Br R²(69) I F

2691 . Br R²(35) I F 2726. Br R²(70) I F

2692. Br R²(36) I F 2727. Br R²(71 ) I F

2693. Br R²(37) I F 2728. Br R²(72) I F

2694. Br R²(38) I F 2729. Br R²(73) I F

2695. Br R²(39) I F 2730. Br R²(74) I F

2696. Br R²(40) I F 2731 . Br R²(75) I F

2697. Br R²(41 ) I F 2732. Br R²(76) I F

2698. Br R²(42) I F 2733. Br R²(77) I F

2699. Br R²(43) I F 2734. Br R²(78) I F

2700. Br R²(44) I F 2735. Br R²(79) I F

2701 . Br R²(45) I F 2736. Br R²(80) I F

2702. Br R²(46) I F 2737. Br R²(81 ) I F

2703. Br R²(47) I F 2738. Br R²(82) I F

2704. Br R²(48) I F 2739. Br R²(83) I F

2705. Br R²(49) I F 2740. Br R²(1 ) I CI No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

2741 . Br R2(2) I CI 2776. Br R2(37) I CI

2742. Br R2(3) I CI 2777. Br R2(38) I CI

2743. Br R2(4) I CI 2778. Br R2(39) I CI

2744. Br R2(5) I CI 2779. Br R2(40) I CI

2745. Br R2(6) I CI 2780. Br R2(41 ) I CI

2746. Br R2(7) I CI 2781 . Br R2(42) I CI

2747. Br R2(8) I CI 2782. Br R2(43) I CI

2748. Br R2(9) I CI 2783. Br R2(44) I CI

2749. Br R2(10) I CI 2784. Br R2(45) I CI

2750. Br R2(1 1 ) I CI 2785. Br R2(46) I CI

2751 . Br R2(12) I CI 2786. Br R2(47) I CI

2752. Br R2(13) I CI 2787. Br R2(48) I CI

2753. Br R2(14) I CI 2788. Br R2(49) I CI

2754. Br R2(15) I CI 2789. Br R2(50) I CI

2755. Br R2(16) I CI 2790. Br R2(51 ) I CI

2756. Br R2(17) I CI 2791 . Br R2(52) I CI

2757. Br R2(18) I CI 2792. Br R2(53) I CI

2758. Br R2(19) I CI 2793. Br R2(54) I CI

2759. Br R2(20) I CI 2794. Br R2(55) I CI

2760. Br R2(21 ) I CI 2795. Br R2(56) I CI

2761 . Br R2(22) I CI 2796. Br R2(57) I CI

2762. Br R2(23) I CI 2797. Br R2(58) I CI

2763. Br R2(24) I CI 2798. Br R2(59) I CI

2764. Br R2(25) I CI 2799. Br R2(60) I CI

2765. Br R2(26) I CI 2800. Br R2(61 ) I CI

2766. Br R2(27) I CI 2801 . Br R2(62) I CI

2767. Br R2(28) I CI 2802. Br R2(63) I CI

2768. Br R2(29) I CI 2803. Br R2(64) I CI

2769. Br R2(30) I CI 2804. Br R2(65) I CI

2770. Br R2(31 ) I CI 2805. Br R2(66) I CI

2771 . Br R2(32) I CI 2806. Br R2(67) I CI

2772. Br R2(33) I CI 2807. Br R2(68) I CI

2773. Br R2(34) I CI 2808. Br R2(69) I CI

2774. Br R2(35) I CI 2809. Br R2(70) I CI

2775. Br R2(36) I CI 2810. Br R2(71 ) I CI No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

281 1 . Br R2(72) I CI 2846. CHs R²(24) I F

2812. Br R²(73) I CI 2847. CHs R²(25) I F

2813. Br R2(74) I CI 2848. CHs R²(26) I F

2814. Br R²(75) I CI 2849. CHs R²(27) I F

2815. Br R²(76) I CI 2850. CHs R²(28) I F

2816. Br R2(77) I CI 2851 . CHs R²(29) I F

2817. Br R²(78) I CI 2852. CHs R²(30) I F

2818. Br R²(79) I CI 2853. CHs R²(31 ) I F

2819. Br R²(80) I CI 2854. CHs R²(32) I F

2820. Br R²(81 ) I CI 2855. CHs R²(33) I F

2821 . Br R²(82) I CI 2856. CHs R²(34) I F

2822. Br R²(83) I CI 2857. CHs R²(35) I F

2823. CHs R²(1 ) I F 2858. CHs R²(36) I F

2824. CHs R²(2) I F 2859. CHs R²(37) I F

2825. CHs R²(3) I F 2860. CHs R²(38) I F

2826. CHs R²(4) I F 2861 . CHs R²(39) I F

2827. CHs R²(5) I F 2862. CHs R²(40) I F

2828. CHs R²(6) I F 2863. CHs R²(41 ) I F

2829. CHs R²(7) I F 2864. CHs R²(42) I F

2830. CHs R²(8) I F 2865. CHs R²(43) I F

2831 . CHs R²(9) I F 2866. CHs R²(44) I F

2832. CHs R²(10) I F 2867. CHs R²(45) I F

2833. CHs R²(1 1 ) I F 2868. CHs R²(46) I F

2834. CHs R²(12) I F 2869. CHs R²(47) I F

2835. CHs R²(13) I F 2870. CHs R²(48) I F

2836. CHs R²(14) I F 2871 . CHs R²(49) I F

2837. CHs R²(15) I F 2872. CHs R²(50) I F

2838. CHs R²(16) I F 2873. CHs R²(51 ) I F

2839. CHs R²(17) I F 2874. CHs R²(52) I F

2840. CHs R²(18) I F 2875. CHs R²(53) I F

2841 . CHs R²(19) I F 2876. CHs R²(54) I F

2842. CHs R²(20) I F 2877. CHs R²(55) I F

2843. CHs R²(21 ) I F 2878. CHs R²(56) I F

2844. CHs R²(22) I F 2879. CHs R²(57) I F

2845. CHs R²(23) I F 2880. CHs R²(58) I F No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

2881 . CHs R²(59) I F 2916. CHs R2(1 1 ) I CI

2882. CHs R²(60) I F 2917. CHs R²(12) I CI

2883. CHs R²(61 ) I F 2918. CHs R²(13) I CI

2884. CHs R²(62) I F 2919. CHs R²(14) I CI

2885. CHs R²(63) I F 2920. CHs R²(15) I CI

2886. CHs R²(64) I F 2921 . CHs R²(16) I CI

2887. CHs R²(65) I F 2922. CHs R²(17) I CI

2888. CHs R²(66) I F 2923. CHs R²(18) I CI

2889. CHs R²(67) I F 2924. CHs R²(19) I CI

2890. CHs R²(68) I F 2925. CHs R²(20) I CI

2891 . CHs R²(69) I F 2926. CHs R²(21 ) I CI

2892. CHs R²(70) I F 2927. CHs R²(22) I CI

2893. CHs R²(71 ) I F 2928. CHs R²(23) I CI

2894. CHs R²(72) I F 2929. CHs R²(24) I CI

2895. CHs R²(73) I F 2930. CHs R²(25) I CI

2896. CHs R²(74) I F 2931 . CHs R²(26) I CI

2897. CHs R²(75) I F 2932. CHs R²(27) I CI

2898. CHs R²(76) I F 2933. CHs R²(28) I CI

2899. CHs R²(77) I F 2934. CHs R²(29) I CI

2900. CHs R²(78) I F 2935. CHs R²(30) I CI

2901 . CHs R²(79) I F 2936. CHs R²(31 ) I CI

2902. CHs R²(80) I F 2937. CHs R²(32) I CI

2903. CHs R²(81 ) I F 2938. CHs R²(33) I CI

2904. CHs R²(82) I F 2939. CHs R²(34) I CI

2905. CHs R²(83) I F 2940. CHs R²(35) I CI

2906. CHs R²(1 ) I CI 2941 . CHs R²(36) I CI

2907. CHs R²(2) I CI 2942. CHs R²(37) I CI

2908. CHs R²(3) I CI 2943. CHs R²(38) I CI

2909. CHs R²(4) I CI 2944. CHs R²(39) I CI

2910. CHs R²(5) I CI 2945. CHs R²(40) I CI

291 1 . CHs R²(6) I CI 2946. CHs R²(41 ) I CI

2912. CHs R²(7) I CI 2947. CHs R²(42) I CI

2913. CHs R²(8) I CI 2948. CHs R²(43) I CI

2914. CHs R²(9) I CI 2949. CHs R²(44) I CI

2915. CHs R²(10) I CI 2950. CHs R²(45) I CI No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

2951 . CHs R²(46) I CI 2986. CHs R²(81 ) I CI

2952. CHs R2(47) I CI 2987. CHs R²(82) I CI

2953. CHs R²(48) I CI 2988. CHs R²(83) I CI

2954. CHs R²(49) I CI 2989. CI R²(84) CI CI

2955. CHs R²(50) I CI 2990. CI R²(85) CI CI

2956. CHs R²(51 ) I CI 2991 . CI R²(86) CI CI

2957. CHs R²(52) I CI 2992. CI R²(87) CI CI

2958. CHs R²(53) I CI 2993. CI R²(88) CI CI

2959. CHs R²(54) I CI 2994. CI R²(89) CI CI

2960. CHs R²(55) I CI 2995. CI R²(90) CI CI

2961 . CHs R²(56) I CI 2996. CI R²(91 ) CI CI

2962. CHs R²(57) I CI 2997. CI R²(92) CI CI

2963. CHs R²(58) I CI 2998. CI R²(93) CI CI

2964. CHs R²(59) I CI 2999. CI R²(94) CI CI

2965. CHs R²(60) I CI 3000. CI R²(95) CI CI

2966. CHs R²(61 ) I CI 3001 . CI R²(84) Br CI

2967. CHs R²(62) I CI 3002. CI R²(85) Br CI

2968. CHs R²(63) I CI 3003. CI R²(86) Br CI

2969. CHs R²(64) I CI 3004. CI R²(87) Br CI

2970. CHs R²(65) I CI 3005. CI R²(88) Br CI

2971 . CHs R²(66) I CI 3006. CI R²(89) Br CI

2972. CHs R²(67) I CI 3007. CI R²(90) Br CI

2973. CHs R²(68) I CI 3008. CI R²(91 ) Br CI

2974. CHs R²(69) I CI 3009. CI R²(92) Br CI

2975. CHs R²(70) I CI 3010. CI R²(93) Br CI

2976. CHs R²(71 ) I CI 301 1 . CI R²(94) Br CI

2977. CHs R²(72) I CI 3012. CI R²(95) Br CI

2978. CHs R²(73) I CI 3013. CI R²(84) I CI

2979. CHs R²(74) I CI 3014. CI R²(85) I CI

2980. CHs R²(75) I CI 3015. CI R²(86) I CI

2981 . CHs R²(76) I CI 3016. CI R²(87) I CI

2982. CHs R²(77) I CI 3017. CI R²(88) I CI

2983. CHs R²(78) I CI 3018. CI R²(89) I CI

2984. CHs R²(79) I CI 3019. CI R²(90) I CI

2985. CHs R²(80) I CI 3020. CI R²(91 ) I CI No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

3021 . CI R²(92) I CI 3056. CI R²(91 ) S(0)₂CHs CI

3022. CI R²(93) I CI 3057. CI R²(92) S(0)₂CHs CI

3023. CI R²(94) I CI 3058. CI R²(93) S(0)₂CHs CI

3024. CI R²(95) I CI 3059. CI R²(94) S(0)₂CHs CI

3025. CI R²(84) CFs CI 3060. CI R²(95) S(0)₂CHs CI

3026. CI R²(85) CFs CI 3061 . CI R²(84) CI F

3027. CI R²(86) CFs CI 3062. CI R²(85) CI F

3028. CI R²(87) CFs CI 3063. CI R²(86) CI F

3029. CI R²(88) CFs CI 3064. CI R²(87) CI F

3030. CI R²(89) CFs CI 3065. CI R²(88) CI F

3031 . CI R²(90) CFs CI 3066. CI R²(89) CI F

3032. CI R²(91 ) CFs CI 3067. CI R²(90) CI F

3033. CI R²(92) CFs CI 3068. CI R²(91 ) CI F

3034. CI R²(93) CFs CI 3069. CI R²(92) CI F

3035. CI R²(94) CFs CI 3070. CI R²(93) CI F

3036. CI R²(95) CFs CI 3071 . CI R²(94) CI F

3037. CI R²(84) SCHs CI 3072. CI R²(95) CI F

3038. CI R²(85) SCHs CI 3073. CI R²(84) Br F

3039. CI R²(86) SCHs CI 3074. CI R²(85) Br F

3040. CI R²(87) SCHs CI 3075. CI R²(86) Br F

3041 . CI R²(88) SCHs CI 3076. CI R²(87) Br F

3042. CI R²(89) SCHs CI 3077. CI R²(88) Br F

3043. CI R²(90) SCHs CI 3078. CI R²(89) Br F

3044. CI R²(91 ) SCHs CI 3079. CI R²(90) Br F

3045. CI R²(92) SCHs CI 3080. CI R²(91 ) Br F

3046. CI R²(93) SCHs CI 3081 . CI R²(92) Br F

3047. CI R²(94) SCHs CI 3082. CI R²(93) Br F

3048. CI R²(95) SCHs CI 3083. CI R²(94) Br F

3049. CI R²(84) S(0)₂CHs CI 3084. CI R²(95) Br F

3050. CI R²(85) S(0)₂CHs CI 3085. CI R²(84) I F

3051 . CI R²(86) S(0)₂CHs CI 3086. CI R²(85) I F

3052. CI R²(87) S(0)₂CHs CI 3087. CI R²(86) I F

3053. CI R²(88) S(0)₂CHs CI 3088. CI R²(87) I F

3054. CI R²(89) S(0)₂CHs CI 3089. CI R²(88) I F

3055. CI R²(90) S(0)₂CHs CI 3090. CI R²(89) I F No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

3091 . CI R²(90) I F 3126. CI R²(89) S(0)₂CHs F

3092. CI R²(91 ) I F 3127. CI R²(90) S(0)₂CHs F

3093. CI R²(92) I F 3128. CI R²(91 ) S(0)₂CHs F

3094. CI R²(93) I F 3129. CI R²(92) S(0)₂CHs F

3095. CI R²(94) I F 3130. CI R²(93) S(0)₂CHs F

3096. CI R²(95) I F 3131 . CI R²(94) S(0)₂CHs F

3097. CI R²(84) CFs F 3132. CI R²(95) S(0)₂CHs F

3098. CI R²(85) CFs F 3133. Br R²(84) CI CI

3099. CI R²(86) CFs F 3134. Br R²(85) CI CI

3100. CI R²(87) CFs F 3135. Br R²(86) CI CI

3101 . CI R²(88) CFs F 3136. Br R²(87) CI CI

3102. CI R²(89) CFs F 3137. Br R²(88) CI CI

3103. CI R²(90) CFs F 3138. Br R²(89) CI CI

3104. CI R²(91 ) CFs F 3139. Br R²(90) CI CI

3105. CI R²(92) CFs F 3140. Br R²(91 ) CI CI

3106. CI R²(93) CFs F 3141 . Br R²(92) CI CI

3107. CI R²(94) CFs F 3142. Br R²(93) CI CI

3108. CI R²(95) CFs F 3143. Br R²(94) CI CI

3109. CI R²(84) SCHs F 3144. Br R²(95) CI CI

31 10. CI R²(85) SCHs F 3145. Br R²(84) Br CI

31 1 1 . CI R²(86) SCHs F 3146. Br R²(85) Br CI

31 12. CI R²(87) SCHs F 3147. Br R²(86) Br CI

31 13. CI R²(88) SCHs F 3148. Br R²(87) Br CI

31 14. CI R²(89) SCHs F 3149. Br R²(88) Br CI

31 15. CI R²(90) SCHs F 3150. Br R²(89) Br CI

31 16. CI R²(91 ) SCHs F 3151 . Br R²(90) Br CI

31 17. CI R²(92) SCHs F 3152. Br R²(91 ) Br CI

31 18. CI R²(93) SCHs F 3153. Br R²(92) Br CI

31 19. CI R²(94) SCHs F 3154. Br R²(93) Br CI

3120. CI R²(95) SCHs F 3155. Br R²(94) Br CI

3121 . CI R²(84) S(0)₂CHs F 3156. Br R²(95) Br CI

3122. CI R²(85) S(0)₂CHs F 3157. Br R²(84) I CI

3123. CI R²(86) S(0)₂CHs F 3158. Br R²(85) I CI

3124. CI R²(87) S(0)₂CHs F 3159. Br R²(86) I CI

3125. CI R²(88) S(0)₂CHs F 3160. Br R²(87) I CI No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

3161 . Br R²(88) I CI 3196. Br R²(87) S(0)₂CHs CI

3162. Br R²(89) I CI 3197. Br R²(88) S(0)₂CHs CI

3163. Br R²(90) I CI 3198. Br R²(89) S(0)₂CHs CI

3164. Br R²(91 ) I CI 3199. Br R²(90) S(0)₂CHs CI

3165. Br R²(92) I CI 3200. Br R²(91 ) S(0)₂CHs CI

3166. Br R²(93) I CI 3201 . Br R²(92) S(0)₂CHs CI

3167. Br R²(94) I CI 3202. Br R²(93) S(0)₂CHs CI

3168. Br R²(95) I CI 3203. Br R²(94) S(0)₂CHs CI

3169. Br R²(84) CFs CI 3204. Br R²(95) S(0)₂CHs CI

3170. Br R²(85) CFs CI 3205. Br R²(84) CI F

3171 . Br R²(86) CFs CI 3206. Br R²(85) CI F

3172. Br R²(87) CFs CI 3207. Br R²(86) CI F

3173. Br R²(88) CFs CI 3208. Br R²(87) CI F

3174. Br R²(89) CFs CI 3209. Br R²(88) CI F

3175. Br R²(90) CFs CI 3210. Br R²(89) CI F

3176. Br R²(91 ) CFs CI 321 1 . Br R²(90) CI F

3177. Br R²(92) CFs CI 3212. Br R²(91 ) CI F

3178. Br R²(93) CFs CI 3213. Br R²(92) CI F

3179. Br R²(94) CFs CI 3214. Br R²(93) CI F

3180. Br R²(95) CFs CI 3215. Br R²(94) CI F

3181 . Br R²(84) SCHs CI 3216. Br R²(95) CI F

3182. Br R²(85) SCHs CI 3217. Br R²(84) Br F

3183. Br R²(86) SCHs CI 3218. Br R²(85) Br F

3184. Br R²(87) SCHs CI 3219. Br R²(86) Br F

3185. Br R²(88) SCHs CI 3220. Br R²(87) Br F

3186. Br R²(89) SCHs CI 3221 . Br R²(88) Br F

3187. Br R²(90) SCHs CI 3222. Br R²(89) Br F

3188. Br R²(91 ) SCHs CI 3223. Br R²(90) Br F

3189. Br R²(92) SCHs CI 3224. Br R²(91 ) Br F

3190. Br R²(93) SCHs CI 3225. Br R²(92) Br F

3191 . Br R²(94) SCHs CI 3226. Br R²(93) Br F

3192. Br R²(95) SCHs CI 3227. Br R²(94) Br F

3193. Br R²(84) S(0)₂CHs CI 3228. Br R²(95) Br F

3194. Br R²(85) S(0)₂CHs CI 3229. Br R²(84) I F

3195. Br R²(86) S(0)₂CHs CI 3230. Br R²(85) I F No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

3231 . Br R²(86) I F 3266. Br R²(85) S(0)₂CHs F

3232. Br R²(87) I F 3267. Br R²(86) S(0)₂CHs F

3233. Br R²(88) I F 3268. Br R²(87) S(0)₂CHs F

3234. Br R²(89) I F 3269. Br R²(88) S(0)₂CHs F

3235. Br R²(90) I F 3270. Br R²(89) S(0)₂CHs F

3236. Br R²(91 ) I F 3271 . Br R²(90) S(0)₂CHs F

3237. Br R²(92) I F 3272. Br R²(91 ) S(0)₂CHs F

3238. Br R²(93) I F 3273. Br R²(92) S(0)₂CHs F

3239. Br R²(94) I F 3274. Br R²(93) S(0)₂CHs F

3240. Br R²(95) I F 3275. Br R²(94) S(0)₂CHs F

3241 . Br R²(84) CFs F 3276. Br R²(95) S(0)₂CHs F

3242. Br R²(85) CFs F 3277. CHs R²(84) CI CI

3243. Br R²(86) CFs F 3278. CHs R²(85) CI CI

3244. Br R²(87) CFs F 3279. CHs R²(86) CI CI

3245. Br R²(88) CFs F 3280. CHs R²(87) CI CI

3246. Br R²(89) CFs F 3281 . CHs R²(88) CI CI

3247. Br R²(90) CFs F 3282. CHs R²(89) CI CI

3248. Br R²(91 ) CFs F 3283. CHs R²(90) CI CI

3249. Br R²(92) CFs F 3284. CHs R²(91 ) CI CI

3250. Br R²(93) CFs F 3285. CHs R²(92) CI CI

3251 . Br R²(94) CFs F 3286. CHs R²(93) CI CI

3252. Br R²(95) CFs F 3287. CHs R²(94) CI CI

3253. Br R²(84) SCHs F 3288. CHs R²(95) CI CI

3254. Br R²(85) SCHs F 3289. CHs R²(84) Br CI

3255. Br R²(86) SCHs F 3290. CHs R²(85) Br CI

3256. Br R²(87) SCHs F 3291 . CHs R²(86) Br CI

3257. Br R²(88) SCHs F 3292. CHs R²(87) Br CI

3258. Br R²(89) SCHs F 3293. CHs R²(88) Br CI

3259. Br R²(90) SCHs F 3294. CHs R²(89) Br CI

3260. Br R²(91 ) SCHs F 3295. CHs R²(90) Br CI

3261 . Br R²(92) SCHs F 3296. CHs R²(91 ) Br CI

3262. Br R²(93) SCHs F 3297. CHs R²(92) Br CI

3263. Br R²(94) SCHs F 3298. CHs R²(93) Br CI

3264. Br R²(95) SCHs F 3299. CHs R²(94) Br CI

3265. Br R²(84) S(0)₂CHs F 3300. CHs R²(95) Br CI No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

3301 . CHs R²(84) I CI 3336. CHs R²(95) SCHs CI

3302. CHs R²(85) I CI 3337. CHs R²(84) S(0)₂CHs CI

3303. CHs R²(86) I CI 3338. CHs R²(85) S(0)₂CHs CI

3304. CHs R²(87) I CI 3339. CHs R²(86) S(0)₂CHs CI

3305. CHs R²(88) I CI 3340. CHs R²(87) S(0)₂CHs CI

3306. CHs R²(89) I CI 3341 . CHs R²(88) S(0)₂CHs CI

3307. CHs R²(90) I CI 3342. CHs R²(89) S(0)₂CHs CI

3308. CHs R²(91 ) I CI 3343. CHs R²(90) S(0)₂CHs CI

3309. CHs R²(92) I CI 3344. CHs R²(91 ) S(0)₂CHs CI

3310. CHs R²(93) I CI 3345. CHs R²(92) S(0)₂CHs CI

331 1 . CHs R²(94) I CI 3346. CHs R²(93) S(0)₂CHs CI

3312. CHs R²(95) I CI 3347. CHs R²(94) S(0)₂CHs CI

3313. CHs R²(84) CFs CI 3348. CHs R²(95) S(0)₂CHs CI

3314. CHs R²(85) CFs CI 3349. CHs R²(84) CI F

3315. CHs R²(86) CFs CI 3350. CHs R²(85) CI F

3316. CHs R²(87) CFs CI 3351 . CHs R²(86) CI F

3317. CHs R²(88) CFs CI 3352. CHs R²(87) CI F

3318. CHs R²(89) CFs CI 3353. CHs R²(88) CI F

3319. CHs R²(90) CFs CI 3354. CHs R²(89) CI F

3320. CHs R²(91 ) CFs CI 3355. CHs R²(90) CI F

3321 . CHs R²(92) CFs CI 3356. CHs R²(91 ) CI F

3322. CHs R²(93) CFs CI 3357. CHs R²(92) CI F

3323. CHs R²(94) CFs CI 3358. CHs R²(93) CI F

3324. CHs R²(95) CFs CI 3359. CHs R²(94) CI F

3325. CHs R²(84) SCHs CI 3360. CHs R²(95) CI F

3326. CHs R²(85) SCHs CI 3361 . CHs R²(84) Br F

3327. CHs R²(86) SCHs CI 3362. CHs R²(85) Br F

3328. CHs R²(87) SCHs CI 3363. CHs R²(86) Br F

3329. CHs R²(88) SCHs CI 3364. CHs R²(87) Br F

3330. CHs R²(89) SCHs CI 3365. CHs R²(88) Br F

3331 . CHs R²(90) SCHs CI 3366. CHs R²(89) Br F

3332. CHs R²(91 ) SCHs CI 3367. CHs R²(90) Br F

3333. CHs R²(92) SCHs CI 3368. CHs R²(91 ) Br F

3334. CHs R²(93) SCHs CI 3369. CHs R²(92) Br F

3335. CHs R²(94) SCHs CI 3370. CHs R²(93) Br F No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

3371 . CHs R²(94) Br F 3406. CHs R²(93) SCHs F

3372. CHs R²(95) Br F 3407. CHs R²(94) SCHs F

3373. CHs R²(84) I F 3408. CHs R²(95) SCHs F

3374. CHs R²(85) I F 3409. CHs R²(84) S(0)₂CHs F

3375. CHs R²(86) I F 3410. CHs R²(85) S(0)₂CHs F

3376. CHs R²(87) I F 341 1 . CHs R²(86) S(0)₂CHs F

3377. CHs R²(88) I F 3412. CHs R²(87) S(0)₂CHs F

3378. CHs R²(89) I F 3413. CHs R²(88) S(0)₂CHs F

3379. CHs R²(90) I F 3414. CHs R²(89) S(0)₂CHs F

3380. CHs R²(91 ) I F 3415. CHs R²(90) S(0)₂CHs F

3381 . CHs R²(92) I F 3416. CHs R²(91 ) S(0)₂CHs F

3382. CHs R²(93) I F 3417. CHs R²(92) S(0)₂CHs F

3383. CHs R²(94) I F 3418. CHs R²(93) S(0)₂CHs F

3384. CHs R²(95) I F 3419. CHs R²(94) S(0)₂CHs F

3385. CHs R²(84) CFs F 3420. CHs R²(95) S(0)₂CHs F

3386. CHs R²(85) CFs F 3421 . CI R²(96) CI F

3387. CHs R²(86) CFs F 3422. CI R²(97) CI F

3388. CHs R²(87) CFs F 3423. CI R²(98) CI F

3389. CHs R²(88) CFs F 3424. CI R²(99) CI F

3390. CHs R²(89) CFs F 3425. CI R²(100) CI F

3391 . CHs R²(90) CFs F 3426. CI R²(101 ) CI F

3392. CHs R²(91 ) CFs F 3427. CI R²(102) CI F

3393. CHs R²(92) CFs F 3428. CI R²(103) CI F

3394. CHs R²(93) CFs F 3429. CI R²(104) CI F

3395. CHs R²(94) CFs F 3430. CI R²(105) CI F

3396. CHs R²(95) CFs F 3431 . CI R²(106) CI F

3397. CHs R²(84) SCHs F 3432. CI R²(107) CI F

3398. CHs R²(85) SCHs F 3433. CI R²(108) CI F

3399. CHs R²(86) SCHs F 3434. CI R²(109) CI F

3400. CHs R²(87) SCHs F 3435. CI R²(1 10) CI F

3401 . CHs R²(88) SCHs F 3436. CI R²(1 1 1 ) CI F

3402. CHs R²(89) SCHs F 3437. CI R²(1 12) CI F

3403. CHs R²(90) SCHs F 3438. CI R²(1 13) CI F

3404. CHs R²(91 ) SCHs F 3439. CI R²(1 14) CI F

3405. CHs R²(92) SCHs F 3440. CI R²(1 15) CI F No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

3441. CI R2(116) CI F 3476. CI R2(115) CI CI

3442. CI R2(117) CI F 3477. CI R2(116) CI CI

3443. CI R2(118) CI F 3478. CI R2(117) CI CI

3444. CI R2(119) CI F 3479. CI R2(118) CI CI

3445. CI R2(120) CI F 3480. CI R2(119) CI CI

3446. CI R2(121) CI F 3481. CI R2(120) CI CI

3447. CI R2(122) CI F 3482. CI R2(121) CI CI

3448. CI R2(123) CI F 3483. CI R2(122) CI CI

3449. CI R2(124) CI F 3484. CI R2(123) CI CI

3450. CI R2(125) CI F 3485. CI R2(124) CI CI

3451. CI R2(126) CI F 3486. CI R2(125) CI CI

3452. CI R2(127) CI F 3487. CI R2(126) CI CI

3453. CI R2(128) CI F 3488. CI R2(127) CI CI

3454. CI R2(129) CI F 3489. CI R2(128) CI CI

3455. CI R2(130) CI F 3490. CI R2(129) CI CI

3456. CI R2(131) CI F 3491. CI R2(130) CI CI

3457. CI R2(96) CI CI 3492. CI R2(131) CI CI

3458. CI R2(97) CI CI 3493. CI R2(96) Br F

3459. CI R2(98) CI CI 3494. CI R2(97) Br F

3460. CI R2(99) CI CI 3495. CI R2(98) Br F

3461. CI R2(100) CI CI 3496. CI R2(99) Br F

3462. CI R2(101) CI CI 3497. CI R2(100) Br F

3463. CI R2(102) CI CI 3498. CI R2(101) Br F

3464. CI R2(103) CI CI 3499. CI R2(102) Br F

3465. CI R2(104) CI CI 3500. CI R2(103) Br F

3466. CI R2(105) CI CI 3501. CI R2(104) Br F

3467. CI R2(106) CI CI 3502. CI R2(105) Br F

3468. CI R2(107) CI CI 3503. CI R2(106) Br F

3469. CI R2(108) CI CI 3504. CI R2(107) Br F

3470. CI R2(109) CI CI 3505. CI R2(108) Br F

3471. CI R2(110) CI CI 3506. CI R2(109) Br F

3472. CI R2(111) CI CI 3507. CI R2(110) Br F

3473. CI R2(112) CI CI 3508. CI R²(111) Br F

3474. CI R2(113) CI CI 3509. CI R2(112) Br F

3475. CI R2(114) CI CI 3510. CI R2(113) Br F No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

3511. CI R2(114) Br F 3546. CI R2(113) Br CI

3512. CI R2(115) Br F 3547. CI R2(114) Br CI

3513. CI R2(116) Br F 3548. CI R2(115) Br CI

3514. CI R2(117) Br F 3549. CI R2(116) Br CI

3515. CI R2(118) Br F 3550. CI R2(117) Br CI

3516. CI R2(119) Br F 3551. CI R2(118) Br CI

3517. CI R2(120) Br F 3552. CI R2(119) Br CI

3518. CI R2(121) Br F 3553. CI R2(120) Br CI

3519. CI R2(122) Br F 3554. CI R2(121) Br CI

3520. CI R2(123) Br F 3555. CI R2(122) Br CI

3521. CI R2(124) Br F 3556. CI R2(123) Br CI

3522. CI R2(125) Br F 3557. CI R2(124) Br CI

3523. CI R2(126) Br F 3558. CI R2(125) Br CI

3524. CI R2(127) Br F 3559. CI R2(126) Br CI

3525. CI R2(128) Br F 3560. CI R2(127) Br CI

3526. CI R2(129) Br F 3561. CI R2(128) Br CI

3527. CI R2(130) Br F 3562. CI R2(129) Br CI

3528. CI R2(131) Br F 3563. CI R2(130) Br CI

3529. CI R2(96) Br CI 3564. CI R2(131) Br CI

3530. CI R2(97) Br CI 3565. CI R2(96) I F

3531. CI R2(98) Br CI 3566. CI R2(97) I F

3532. CI R2(99) Br CI 3567. CI R2(98) I F

3533. CI R2(100) Br CI 3568. CI R2(99) I F

3534. CI R2(101) Br CI 3569. CI R2(100) I F

3535. CI R2(102) Br CI 3570. CI R2(101) I F

3536. CI R2(103) Br CI 3571. CI R2(102) I F

3537. CI R2(104) Br CI 3572. CI R2(103) I F

3538. CI R2(105) Br CI 3573. CI R2(104) I F

3539. CI R2(106) Br CI 3574. CI R2(105) I F

3540. CI R2(107) Br CI 3575. CI R2(106) I F

3541. CI R2(108) Br CI 3576. CI R2(107) I F

3542. CI R2(109) Br CI 3577. CI R2(108) I F

3543. CI R2(110) Br CI 3578. CI R2(109) I F

3544. CI R2(111) Br CI 3579. CI R2(110) I F

3545. CI R2(112) Br CI 3580. CI R²(111) I F No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

3581. CI R2(112) I F 3616. CI R²(111) I CI

3582. CI R2(113) I F 3617. CI R2(112) I CI

3583. CI R2(114) I F 3618. CI R2(113) I CI

3584. CI R2(115) I F 3619. CI R2(114) I CI

3585. CI R2(116) I F 3620. CI R2(115) I CI

3586. CI R2(117) I F 3621. CI R2(116) I CI

3587. CI R2(118) I F 3622. CI R2(117) I CI

3588. CI R2(119) I F 3623. CI R2(118) I CI

3589. CI R2(120) I F 3624. CI R2(119) I CI

3590. CI R2(121) I F 3625. CI R2(120) I CI

3591. CI R2(122) I F 3626. CI R2(121) I CI

3592. CI R2(123) I F 3627. CI R2(122) I CI

3593. CI R2(124) I F 3628. CI R2(123) I CI

3594. CI R2(125) I F 3629. CI R2(124) I CI

3595. CI R2(126) I F 3630. CI R2(125) I CI

3596. CI R2(127) I F 3631. CI R2(126) I CI

3597. CI R2(128) I F 3632. CI R2(127) I CI

3598. CI R2(129) I F 3633. CI R2(128) I CI

3599. CI R2(130) I F 3634. CI R2(129) I CI

3600. CI R2(131) I F 3635. CI R2(130) I CI

3601. CI R2(96) I CI 3636. CI R2(131) I CI

3602. CI R2(97) I CI 3637. CI R2(96) CFs F

3603. CI R2(98) I CI 3638. CI R2(97) CFs F

3604. CI R2(99) I CI 3639. CI R2(98) CFs F

3605. CI R2(100) I CI 3640. CI R2(99) CFs F

3606. CI R2(101) I CI 3641. CI R2(100) CFs F

3607. CI R2(102) I CI 3642. CI R2(101) CFs F

3608. CI R2(103) I CI 3643. CI R2(102) CFs F

3609. CI R2(104) I CI 3644. CI R2(103) CFs F

3610. CI R2(105) I CI 3645. CI R2(104) CFs F

3611. CI R2(106) I CI 3646. CI R2(105) CFs F

3612. CI R2(107) I CI 3647. CI R2(106) CFs F

3613. CI R2(108) I CI 3648. CI R2(107) CFs F

3614. CI R2(109) I CI 3649. CI R2(108) CFs F

3615. CI R2(110) I CI 3650. CI R2(109) CFs F No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

3651. CI R2(110) CFs F 3686. CI R2(109) CFs CI

3652. CI R2(111) CFs F 3687. CI R2(110) CFs CI

3653. CI R2(112) CFs F 3688. CI R²(111) CFs CI

3654. CI R2(113) CFs F 3689. CI R2(112) CFs CI

3655. CI R2(114) CFs F 3690. CI R2(113) CFs CI

3656. CI R2(115) CFs F 3691. CI R2(114) CFs CI

3657. CI R2(116) CFs F 3692. CI R2(115) CFs CI

3658. CI R2(117) CFs F 3693. CI R2(116) CFs CI

3659. CI R2(118) CFs F 3694. CI R2(117) CFs CI

3660. CI R2(119) CFs F 3695. CI R2(118) CFs CI

3661. CI R2(120) CFs F 3696. CI R2(119) CFs CI

3662. CI R2(121) CFs F 3697. CI R2(120) CFs CI

3663. CI R2(122) CFs F 3698. CI R2(121) CFs CI

3664. CI R2(123) CFs F 3699. CI R2(122) CFs CI

3665. CI R2(124) CFs F 3700. CI R2(123) CFs CI

3666. CI R2(125) CFs F 3701. CI R2(124) CFs CI

3667. CI R2(126) CFs F 3702. CI R2(125) CFs CI

3668. CI R2(127) CFs F 3703. CI R2(126) CFs CI

3669. CI R2(128) CFs F 3704. CI R2(127) CFs CI

3670. CI R2(129) CFs F 3705. CI R2(128) CFs CI

3671. CI R2(130) CFs F 3706. CI R2(129) CFs CI

3672. CI R2(131) CFs F 3707. CI R2(130) CFs CI

3673. CI R2(96) CFs CI 3708. CI R2(131) CFs CI

3674. CI R2(97) CFs CI 3709. CI R2(96) SCHs F

3675. CI R2(98) CFs CI 3710. CI R2(97) SCHs F

3676. CI R2(99) CFs CI 3711. CI R2(98) SCHs F

3677. CI R2(100) CFs CI 3712. CI R2(99) SCHs F

3678. CI R2(101) CFs CI 3713. CI R2(100) SCHs F

3679. CI R2(102) CFs CI 3714. CI R2(101) SCHs F

3680. CI R2(103) CFs CI 3715. CI R2(102) SCHs F

3681. CI R2(104) CFs CI 3716. CI R2(103) SCHs F

3682. CI R2(105) CFs CI 3717. CI R2(104) SCHs F

3683. CI R2(106) CFs CI 3718. CI R2(105) SCHs F

3684. CI R2(107) CFs CI 3719. CI R2(106) SCHs F

3685. CI R2(108) CFs CI 3720. CI R2(107) SCHs F No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

3721. CI R²(108) SCHs F 3756. CI R2(107) SCHs CI

3722. CI R²(109) SCHs F 3757. CI R2(108) SCHs CI

3723. CI R2(110) SCHs F 3758. CI R2(109) SCHs CI

3724. CI R2(111) SCHs F 3759. CI R2(110) SCHs CI

3725. CI R2(112) SCHs F 3760. CI R²(111) SCHs CI

3726. CI R2(113) SCHs F 3761. CI R2(112) SCHs CI

3727. CI R2(114) SCHs F 3762. CI R2(113) SCHs CI

3728. CI R2(115) SCHs F 3763. CI R2(114) SCHs CI

3729. CI R2(116) SCHs F 3764. CI R2(115) SCHs CI

3730. CI R2(117) SCHs F 3765. CI R2(116) SCHs CI

3731. CI R2(118) SCHs F 3766. CI R2(117) SCHs CI

3732. CI R2(119) SCHs F 3767. CI R2(118) SCHs CI

3733. CI R2(120) SCHs F 3768. CI R2(119) SCHs CI

3734. CI R2(121) SCHs F 3769. CI R2(120) SCHs CI

3735. CI R2(122) SCHs F 3770. CI R2(121) SCHs CI

3736. CI R2(123) SCHs F 3771. CI R2(122) SCHs CI

3737. CI R2(124) SCHs F 3772. CI R2(123) SCHs CI

3738. CI R2(125) SCHs F 3773. CI R2(124) SCHs CI

3739. CI R2(126) SCHs F 3774. CI R2(125) SCHs CI

3740. CI R2(127) SCHs F 3775. CI R2(126) SCHs CI

3741. CI R2(128) SCHs F 3776. CI R2(127) SCHs CI

3742. CI R2(129) SCHs F 3777. CI R2(128) SCHs CI

3743. CI R2(130) SCHs F 3778. CI R2(129) SCHs CI

3744. CI R2(131) SCHs F 3779. CI R2(130) SCHs CI

3745. CI R2(96) SCHs CI 3780. CI R2(131) SCHs CI

3746. CI R2(97) SCHs CI 3781. CI R2(96) S(0)₂CHs F

3747. CI R2(98) SCHs CI 3782. CI R2(97) S(0)₂CHs F

3748. CI R2(99) SCHs CI 3783. CI R2(98) S(0)₂CHs F

3749. CI R2(100) SCHs CI 3784. CI R2(99) S(0)₂CHs F

3750. CI R2(101) SCHs CI 3785. CI R2(100) S(0)₂CHs F

3751. CI R2(102) SCHs CI 3786. CI R2(101) S(0)₂CHs F

3752. CI R2(103) SCHs CI 3787. CI R2(102) S(0)₂CHs F

3753. CI R2(104) SCHs CI 3788. CI R2(103) S(0)₂CHs F

3754. CI R2(105) SCHs CI 3789. CI R2(104) S(0)₂CHs F

3755. CI R2(106) SCHs CI 3790. CI R2(105) S(0)₂CHs F No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

3791 . CI R²(106) S(0)₂CH₃ F 3826. CI R2(105) S(0)₂CH₃ CI

3792. CI R2(107) S(0)₂CH₃ F 3827. CI R2(106) S(0)₂CH₃ CI

3793. CI R²(108) S(0)₂CH₃ F 3828. CI R2(107) S(0)₂CH₃ CI

3794. CI R²(109) S(0)₂CH₃ F 3829. CI R2(108) S(0)₂CH₃ CI

3795. CI R2(1 10) S(0)₂CH₃ F 3830. CI R2(109) S(0)₂CH₃ CI

3796. CI R2(1 1 1 ) S(0)₂CH₃ F 3831 . CI R2(1 10) S(0)₂CH₃ CI

3797. CI R2(1 12) S(0)₂CH₃ F 3832. CI R²(1 1 1 ) S(0)₂CH₃ CI

3798. CI R2(1 13) S(0)₂CH₃ F 3833. CI R2(1 12) S(0)₂CH₃ CI

3799. CI R2(1 14) S(0)₂CH₃ F 3834. CI R2(1 13) S(0)₂CH₃ CI

3800. CI R2(1 15) S(0)₂CH₃ F 3835. CI R2(1 14) S(0)₂CH₃ CI

3801 . CI R2(1 16) S(0)₂CH₃ F 3836. CI R2(1 15) S(0)₂CH₃ CI

3802. CI R2(1 17) S(0)₂CH₃ F 3837. CI R2(1 16) S(0)₂CH₃ CI

3803. CI R2(1 18) S(0)₂CH₃ F 3838. CI R2(1 17) S(0)₂CH₃ CI

3804. CI R2(1 19) S(0)₂CH₃ F 3839. CI R2(1 18) S(0)₂CH₃ CI

3805. CI R2(120) S(0)₂CH₃ F 3840. CI R2(1 19) S(0)₂CH₃ CI

3806. CI R2(121 ) S(0)₂CH₃ F 3841 . CI R2(120) S(0)₂CH₃ CI

3807. CI R2(122) S(0)₂CH₃ F 3842. CI R2(121 ) S(0)₂CH₃ CI

3808. CI R2(123) S(0)₂CH₃ F 3843. CI R2(122) S(0)₂CH₃ CI

3809. CI R2(124) S(0)₂CH₃ F 3844. CI R2(123) S(0)₂CH₃ CI

3810. CI R2(125) S(0)₂CH₃ F 3845. CI R2(124) S(0)₂CH₃ CI

381 1 . CI R2(126) S(0)₂CH₃ F 3846. CI R2(125) S(0)₂CH₃ CI

3812. CI R2(127) S(0)₂CH₃ F 3847. CI R2(126) S(0)₂CH₃ CI

3813. CI R2(128) S(0)₂CH₃ F 3848. CI R2(127) S(0)₂CH₃ CI

3814. CI R2(129) S(0)₂CH₃ F 3849. CI R2(128) S(0)₂CH₃ CI

3815. CI R2(130) S(0)₂CH₃ F 3850. CI R2(129) S(0)₂CH₃ CI

3816. CI R2(131 ) S(0)₂CH₃ F 3851 . CI R2(130) S(0)₂CH₃ CI

3817. CI R2(96) S(0)₂CH₃ CI 3852. CI R2(131 ) S(0)₂CH₃ CI

3818. CI R2(97) S(0)₂CH₃ CI 3853. Br R2(96) CI F

3819. CI R2(98) S(0)₂CH₃ CI 3854. Br R2(97) CI F

3820. CI R2(99) S(0)₂CH₃ CI 3855. Br R2(98) CI F

3821 . CI R2(100) S(0)₂CH₃ CI 3856. Br R2(99) CI F

3822. CI R2(101 ) S(0)₂CH₃ CI 3857. Br R2(100) CI F

3823. CI R2(102) S(0)₂CH₃ CI 3858. Br R2(101 ) CI F

3824. CI R2(103) S(0)₂CH₃ CI 3859. Br R2(102) CI F

3825. CI R2(104) S(0)₂CH₃ CI 3860. Br R2(103) CI F No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

3861. Br R2(104) CI F 3896. Br R2(103) CI CI

3862. Br R²(105) CI F 3897. Br R2(104) CI CI

3863. Br R²(106) CI F 3898. Br R2(105) CI CI

3864. Br R2(107) CI F 3899. Br R2(106) CI CI

3865. Br R²(108) CI F 3900. Br R2(107) CI CI

3866. Br R²(109) CI F 3901. Br R2(108) CI CI

3867. Br R2(110) CI F 3902. Br R2(109) CI CI

3868. Br R2(111) CI F 3903. Br R2(110) CI CI

3869. Br R2(112) CI F 3904. Br R²(111) CI CI

3870. Br R2(113) CI F 3905. Br R2(112) CI CI

3871. Br R2(114) CI F 3906. Br R2(113) CI CI

3872. Br R2(115) CI F 3907. Br R2(114) CI CI

3873. Br R2(116) CI F 3908. Br R2(115) CI CI

3874. Br R2(117) CI F 3909. Br R2(116) CI CI

3875. Br R2(118) CI F 3910. Br R2(117) CI CI

3876. Br R2(119) CI F 3911. Br R2(118) CI CI

3877. Br R2(120) CI F 3912. Br R2(119) CI CI

3878. Br R2(121) CI F 3913. Br R2(120) CI CI

3879. Br R2(122) CI F 3914. Br R2(121) CI CI

3880. Br R2(123) CI F 3915. Br R2(122) CI CI

3881. Br R2(124) CI F 3916. Br R2(123) CI CI

3882. Br R2(125) CI F 3917. Br R2(124) CI CI

3883. Br R2(126) CI F 3918. Br R2(125) CI CI

3884. Br R2(127) CI F 3919. Br R2(126) CI CI

3885. Br R2(128) CI F 3920. Br R2(127) CI CI

3886. Br R2(129) CI F 3921. Br R2(128) CI CI

3887. Br R2(130) CI F 3922. Br R2(129) CI CI

3888. Br R2(131) CI F 3923. Br R2(130) CI CI

3889. Br R2(96) CI CI 3924. Br R2(131) CI CI

3890. Br R2(97) CI CI 3925. Br R2(96) Br F

3891. Br R2(98) CI CI 3926. Br R2(97) Br F

3892. Br R2(99) CI CI 3927. Br R2(98) Br F

3893. Br R2(100) CI CI 3928. Br R2(99) Br F

3894. Br R2(101) CI CI 3929. Br R2(100) Br F

3895. Br R2(102) CI CI 3930. Br R2(101) Br F No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

3931. Br R2(102) Br F 3966. Br R²(101) Br CI

3932. Br R²(103) Br F 3967. Br R²(102) Br CI

3933. Br R2(104) Br F 3968. Br R²(103) Br CI

3934. Br R²(105) Br F 3969. Br R²(104) Br CI

3935. Br R²(106) Br F 3970. Br R²(105) Br CI

3936. Br R²(107) Br F 3971. Br R²(106) Br CI

3937. Br R²(108) Br F 3972. Br R²(107) Br CI

3938. Br R²(109) Br F 3973. Br R²(108) Br CI

3939. Br R²(110) Br F 3974. Br R²(109) Br CI

3940. Br R²(111) Br F 3975. Br R²(110) Br CI

3941. Br R²(112) Br F 3976. Br R²(111) Br CI

3942. Br R²(113) Br F 3977. Br R²(112) Br CI

3943. Br R²(114) Br F 3978. Br R²(113) Br CI

3944. Br R²(115) Br F 3979. Br R²(114) Br CI

3945. Br R²(116) Br F 3980. Br R²(115) Br CI

3946. Br R²(117) Br F 3981. Br R²(116) Br CI

3947. Br R²(118) Br F 3982. Br R²(117) Br CI

3948. Br R²(119) Br F 3983. Br R²(118) Br CI

3949. Br R²(120) Br F 3984. Br R²(119) Br CI

3950. Br R²(121) Br F 3985. Br R²(120) Br CI

3951. Br R²(122) Br F 3986. Br R²(121) Br CI

3952. Br R²(123) Br F 3987. Br R²(122) Br CI

3953. Br R²(124) Br F 3988. Br R²(123) Br CI

3954. Br R²(125) Br F 3989. Br R²(124) Br CI

3955. Br R²(126) Br F 3990. Br R²(125) Br CI

3956. Br R²(127) Br F 3991. Br R²(126) Br CI

3957. Br R²(128) Br F 3992. Br R²(127) Br CI

3958. Br R²(129) Br F 3993. Br R²(128) Br CI

3959. Br R²(130) Br F 3994. Br R²(129) Br CI

3960. Br R²(131) Br F 3995. Br R²(130) Br CI

3961. Br R²(96) Br CI 3996. Br R²(131) Br CI

3962. Br R²(97) Br CI 3997. Br R²(96) I F

3963. Br R²(98) Br CI 3998. Br R²(97) I F

3964. Br R²(99) Br CI 3999. Br R²(98) I F

3965. Br R²(100) Br CI 4000. Br R²(99) I F No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

4001. Br R²(100) I F 4036. Br R2(99) I CI

4002. Br R2(101) I F 4037. Br R2(100) I CI

4003. Br R2(102) I F 4038. Br R2(101) I CI

4004. Br R2(103) I F 4039. Br R2(102) I CI

4005. Br R2(104) I F 4040. Br R2(103) I CI

4006. Br R2(105) I F 4041. Br R2(104) I CI

4007. Br R2(106) I F 4042. Br R2(105) I CI

4008. Br R2(107) I F 4043. Br R2(106) I CI

4009. Br R2(108) I F 4044. Br R2(107) I CI

4010. Br R2(109) I F 4045. Br R2(108) I CI

4011. Br R2(110) I F 4046. Br R2(109) I CI

4012. Br R2(111) I F 4047. Br R2(110) I CI

4013. Br R2(112) I F 4048. Br R²(111) I CI

4014. Br R2(113) I F 4049. Br R2(112) I CI

4015. Br R2(114) I F 4050. Br R2(113) I CI

4016. Br R2(115) I F 4051. Br R2(114) I CI

4017. Br R2(116) I F 4052. Br R2(115) I CI

4018. Br R2(117) I F 4053. Br R2(116) I CI

4019. Br R2(118) I F 4054. Br R2(117) I CI

4020. Br R2(119) I F 4055. Br R2(118) I CI

4021. Br R2(120) I F 4056. Br R2(119) I CI

4022. Br R2(121) I F 4057. Br R2(120) I CI

4023. Br R2(122) I F 4058. Br R2(121) I CI

4024. Br R2(123) I F 4059. Br R2(122) I CI

4025. Br R2(124) I F 4060. Br R2(123) I CI

4026. Br R2(125) I F 4061. Br R2(124) I CI

4027. Br R2(126) I F 4062. Br R2(125) I CI

4028. Br R2(127) I F 4063. Br R2(126) I CI

4029. Br R2(128) I F 4064. Br R2(127) I CI

4030. Br R2(129) I F 4065. Br R2(128) I CI

4031. Br R2(130) I F 4066. Br R2(129) I CI

4032. Br R2(131) I F 4067. Br R2(130) I CI

4033. Br R2(96) I CI 4068. Br R2(131) I CI

4034. Br R2(97) I CI 4069. Br R2(96) CFs F

4035. Br R2(98) I CI 4070. Br R2(97) CFs F No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

4071. Br R²(98) CFs F 4106. Br R2(97) CFs CI

4072. Br R²(99) CFs F 4107. Br R2(98) CFs CI

4073. Br R²(100) CFs F 4108. Br R2(99) CFs CI

4074. Br R2(101) CFs F 4109. Br R2(100) CFs CI

4075. Br R2(102) CFs F 4110. Br R2(101) CFs CI

4076. Br R2(103) CFs F 4111. Br R2(102) CFs CI

4077. Br R2(104) CFs F 4112. Br R2(103) CFs CI

4078. Br R2(105) CFs F 4113. Br R2(104) CFs CI

4079. Br R2(106) CFs F 4114. Br R2(105) CFs CI

4080. Br R2(107) CFs F 4115. Br R2(106) CFs CI

4081. Br R2(108) CFs F 4116. Br R2(107) CFs CI

4082. Br R2(109) CFs F 4117. Br R2(108) CFs CI

4083. Br R2(110) CFs F 4118. Br R2(109) CFs CI

4084. Br R2(111) CFs F 4119. Br R2(110) CFs CI

4085. Br R2(112) CFs F 4120. Br R²(111) CFs CI

4086. Br R2(113) CFs F 4121. Br R2(112) CFs CI

4087. Br R2(114) CFs F 4122. Br R2(113) CFs CI

4088. Br R2(115) CFs F 4123. Br R2(114) CFs CI

4089. Br R2(116) CFs F 4124. Br R2(115) CFs CI

4090. Br R2(117) CFs F 4125. Br R2(116) CFs CI

4091. Br R2(118) CFs F 4126. Br R2(117) CFs CI

4092. Br R2(119) CFs F 4127. Br R2(118) CFs CI

4093. Br R2(120) CFs F 4128. Br R2(119) CFs CI

4094. Br R2(121) CFs F 4129. Br R2(120) CFs CI

4095. Br R2(122) CFs F 4130. Br R2(121) CFs CI

4096. Br R2(123) CFs F 4131. Br R2(122) CFs CI

4097. Br R2(124) CFs F 4132. Br R2(123) CFs CI

4098. Br R2(125) CFs F 4133. Br R2(124) CFs CI

4099. Br R2(126) CFs F 4134. Br R2(125) CFs CI

4100. Br R2(127) CFs F 4135. Br R2(126) CFs CI

4101. Br R2(128) CFs F 4136. Br R2(127) CFs CI

4102. Br R2(129) CFs F 4137. Br R2(128) CFs CI

4103. Br R2(130) CFs F 4138. Br R2(129) CFs CI

4104. Br R2(131) CFs F 4139. Br R2(130) CFs CI

4105. Br R2(96) CFs CI 4140. Br R2(131) CFs CI No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

4141. Br R2( 96) SCHs F 4176. Br R2(131) SCHs F

4142. Br R2( 97) SCHs F 4177. Br R2(96) SCHs CI

4143. Br R2( 98) SCHs F 4178. Br R2(97) SCHs CI

4144. Br R2( 99) SCHs F 4179. Br R2(98) SCHs CI

4145. Br R2( 100) SCHs F 4180. Br R2(99) SCHs CI

4146. Br R2( 101) SCHs F 4181. Br R2(100) SCHs CI

4147. Br R2( 102) SCHs F 4182. Br R2(101) SCHs CI

4148. Br R2( 103) SCHs F 4183. Br R2(102) SCHs CI

4149. Br R2( 104) SCHs F 4184. Br R2(103) SCHs CI

4150. Br R2( 105) SCHs F 4185. Br R2(104) SCHs CI

4151. Br R2( 106) SCHs F 4186. Br R2(105) SCHs CI

4152. Br R2( 107) SCHs F 4187. Br R2(106) SCHs CI

4153. Br R2( 108) SCHs F 4188. Br R2(107) SCHs CI

4154. Br R2( 109) SCHs F 4189. Br R2(108) SCHs CI

4155. Br R2( 110) SCHs F 4190. Br R2(109) SCHs CI

4156. Br R2( 111) SCHs F 4191. Br R2(110) SCHs CI

4157. Br R2( 112) SCHs F 4192. Br R²(111) SCHs CI

4158. Br R2( 113) SCHs F 4193. Br R2(112) SCHs CI

4159. Br R2( 114) SCHs F 4194. Br R2(113) SCHs CI

4160. Br R2( 115) SCHs F 4195. Br R2(114) SCHs CI

4161. Br R2( 116) SCHs F 4196. Br R2(115) SCHs CI

4162. Br R2( 117) SCHs F 4197. Br R2(116) SCHs CI

4163. Br R2( 118) SCHs F 4198. Br R2(117) SCHs CI

4164. Br R2( 119) SCHs F 4199. Br R2(118) SCHs CI

4165. Br R2( 120) SCHs F 4200. Br R2(119) SCHs CI

4166. Br R2( 121) SCHs F 4201. Br R2(120) SCHs CI

4167. Br R2( 122) SCHs F 4202. Br R2(121) SCHs CI

4168. Br R2( 123) SCHs F 4203. Br R2(122) SCHs CI

4169. Br R2( 124) SCHs F 4204. Br R2(123) SCHs CI

4170. Br R2( 125) SCHs F 4205. Br R2(124) SCHs CI

4171. Br R2( 126) SCHs F 4206. Br R2(125) SCHs CI

4172. Br R2( 127) SCHs F 4207. Br R2(126) SCHs CI

4173. Br R2( 128) SCHs F 4208. Br R2(127) SCHs CI

4174. Br R2( 129) SCHs F 4209. Br R2(128) SCHs CI

4175. Br R2( 130) SCHs F 4210. Br R2(129) SCHs CI No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

421 1 . Br R²(130) SCHs CI 4246. Br R²(129) S(0)₂CH₃ F

4212. Br R2(131 ) SCHs CI 4247. Br R²(130) S(0)₂CH₃ F

4213. Br R²(96) S(0)₂CH₃ F 4248. Br R²(131 ) S(0)₂CH₃ F

4214. Br R²(97) S(0)₂CH₃ F 4249. Br R²(96) S(0)₂CH₃ CI

4215. Br R²(98) S(0)₂CH₃ F 4250. Br R²(97) S(0)₂CH₃ CI

4216. Br R²(99) S(0)₂CH₃ F 4251 . Br R²(98) S(0)₂CH₃ CI

4217. Br R²(100) S(0)₂CH₃ F 4252. Br R²(99) S(0)₂CH₃ CI

4218. Br R²(101 ) S(0)₂CH₃ F 4253. Br R²(100) S(0)₂CH₃ CI

4219. Br R²(102) S(0)₂CH₃ F 4254. Br R²(101 ) S(0)₂CH₃ CI

4220. Br R²(103) S(0)₂CH₃ F 4255. Br R²(102) S(0)₂CH₃ CI

4221 . Br R²(104) S(0)₂CH₃ F 4256. Br R²(103) S(0)₂CH₃ CI

4222. Br R²(105) S(0)₂CH₃ F 4257. Br R²(104) S(0)₂CH₃ CI

4223. Br R²(106) S(0)₂CH₃ F 4258. Br R²(105) S(0)₂CH₃ CI

4224. Br R²(107) S(0)₂CH₃ F 4259. Br R²(106) S(0)₂CH₃ CI

4225. Br R²(108) S(0)₂CH₃ F 4260. Br R²(107) S(0)₂CH₃ CI

4226. Br R²(109) S(0)₂CH₃ F 4261 . Br R²(108) S(0)₂CH₃ CI

4227. Br R²(1 10) S(0)₂CH₃ F 4262. Br R²(109) S(0)₂CH₃ CI

4228. Br R²(1 1 1 ) S(0)₂CH₃ F 4263. Br R²(1 10) S(0)₂CH₃ CI

4229. Br R²(1 12) S(0)₂CH₃ F 4264. Br R²(1 1 1 ) S(0)₂CH₃ CI

4230. Br R²(1 13) S(0)₂CH₃ F 4265. Br R²(1 12) S(0)₂CH₃ CI

4231 . Br R²(1 14) S(0)₂CH₃ F 4266. Br R²(1 13) S(0)₂CH₃ CI

4232. Br R²(1 15) S(0)₂CH₃ F 4267. Br R²(1 14) S(0)₂CH₃ CI

4233. Br R²(1 16) S(0)₂CH₃ F 4268. Br R²(1 15) S(0)₂CH₃ CI

4234. Br R²(1 17) S(0)₂CH₃ F 4269. Br R²(1 16) S(0)₂CH₃ CI

4235. Br R²(1 18) S(0)₂CH₃ F 4270. Br R²(1 17) S(0)₂CH₃ CI

4236. Br R²(1 19) S(0)₂CH₃ F 4271 . Br R²(1 18) S(0)₂CH₃ CI

4237. Br R²(120) S(0)₂CH₃ F 4272. Br R²(1 19) S(0)₂CH₃ CI

4238. Br R²(121 ) S(0)₂CH₃ F 4273. Br R²(120) S(0)₂CH₃ CI

4239. Br R²(122) S(0)₂CH₃ F 4274. Br R²(121 ) S(0)₂CH₃ CI

4240. Br R²(123) S(0)₂CH₃ F 4275. Br R²(122) S(0)₂CH₃ CI

4241 . Br R²(124) S(0)₂CH₃ F 4276. Br R²(123) S(0)₂CH₃ CI

4242. Br R²(125) S(0)₂CH₃ F 4277. Br R²(124) S(0)₂CH₃ CI

4243. Br R²(126) S(0)₂CH₃ F 4278. Br R²(125) S(0)₂CH₃ CI

4244. Br R²(127) S(0)₂CH₃ F 4279. Br R²(126) S(0)₂CH₃ CI

4245. Br R²(128) S(0)₂CH₃ F 4280. Br R²(127) S(0)₂CH₃ CI No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

4281. Br R2(128) S(0)₂CHs CI 4316. CHs R²(127) CI F

4282. Br R2(129) S(0)₂CHs CI 4317. CHs R²(128) CI F

4283. Br R²(130) S(0)₂CHs CI 4318. CHs R²(129) CI F

4284. Br R2(131) S(0)₂CHs CI 4319. CHs R²(130) CI F

4285. CHs R²(96) CI F 4320. CHs R²(131) CI F

4286. CHs R²(97) CI F 4321. CHs R²(96) CI CI

4287. CHs R²(98) CI F 4322. CHs R²(97) CI CI

4288. CHs R²(99) CI F 4323. CHs R²(98) CI CI

4289. CHs R²(100) CI F 4324. CHs R²(99) CI CI

4290. CHs R²(101) CI F 4325. CHs R²(100) CI CI

4291. CHs R²(102) CI F 4326. CHs R²(101) CI CI

4292. CHs R²(103) CI F 4327. CHs R²(102) CI CI

4293. CHs R²(104) CI F 4328. CHs R²(103) CI CI

4294. CHs R²(105) CI F 4329. CHs R²(104) CI CI

4295. CHs R²(106) CI F 4330. CHs R²(105) CI CI

4296. CHs R²(107) CI F 4331. CHs R²(106) CI CI

4297. CHs R²(108) CI F 4332. CHs R²(107) CI CI

4298. CHs R²(109) CI F 4333. CHs R²(108) CI CI

4299. CHs R²(110) CI F 4334. CHs R²(109) CI CI

4300. CHs R²(111) CI F 4335. CHs R²(110) CI CI

4301. CHs R²(112) CI F 4336. CHs R²(111) CI CI

4302. CHs R²(113) CI F 4337. CHs R²(112) CI CI

4303. CHs R²(114) CI F 4338. CHs R²(113) CI CI

4304. CHs R²(115) CI F 4339. CHs R²(114) CI CI

4305. CHs R²(116) CI F 4340. CHs R²(115) CI CI

4306. CHs R²(117) CI F 4341. CHs R²(116) CI CI

4307. CHs R²(118) CI F 4342. CHs R²(117) CI CI

4308. CHs R²(119) CI F 4343. CHs R²(118) CI CI

4309. CHs R²(120) CI F 4344. CHs R²(119) CI CI

4310. CHs R²(121) CI F 4345. CHs R²(120) CI CI

4311. CHs R²(122) CI F 4346. CHs R²(121) CI CI

4312. CHs R²(123) CI F 4347. CHs R²(122) CI CI

4313. CHs R²(124) CI F 4348. CHs R²(123) CI CI

4314. CHs R²(125) CI F 4349. CHs R²(124) CI CI

4315. CHs R²(126) CI F 4350. CHs R²(125) CI CI No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

4351. CHs R2(126) CI CI 4386. CHs R2(125) Br F

4352. CHs R2(127) CI CI 4387. CHs R2(126) Br F

4353. CHs R2(128) CI CI 4388. CHs R2(127) Br F

4354. CHs R2(129) CI CI 4389. CHs R2(128) Br F

4355. CHs R2(130) CI CI 4390. CHs R2(129) Br F

4356. CHs R2(131) CI CI 4391. CHs R2(130) Br F

4357. CHs R2(96) Br F 4392. CHs R2(131) Br F

4358. CHs R2(97) Br F 4393. CHs R2(96) Br CI

4359. CHs R2(98) Br F 4394. CHs R2(97) Br CI

4360. CHs R2(99) Br F 4395. CHs R2(98) Br CI

4361. CHs R2(100) Br F 4396. CHs R2(99) Br CI

4362. CHs R2(101) Br F 4397. CHs R2(100) Br CI

4363. CHs R2(102) Br F 4398. CHs R2(101) Br CI

4364. CHs R2(103) Br F 4399. CHs R2(102) Br CI

4365. CHs R2(104) Br F 4400. CHs R2(103) Br CI

4366. CHs R2(105) Br F 4401. CHs R2(104) Br CI

4367. CHs R2(106) Br F 4402. CHs R2(105) Br CI

4368. CHs R2(107) Br F 4403. CHs R2(106) Br CI

4369. CHs R2(108) Br F 4404. CHs R2(107) Br CI

4370. CHs R2(109) Br F 4405. CHs R2(108) Br CI

4371. CHs R2(110) Br F 4406. CHs R2(109) Br CI

4372. CHs R2(111) Br F 4407. CHs R2(110) Br CI

4373. CHs R2(112) Br F 4408. CHs R²(111) Br CI

4374. CHs R2(113) Br F 4409. CHs R2(112) Br CI

4375. CHs R2(114) Br F 4410. CHs R2(113) Br CI

4376. CHs R2(115) Br F 4411. CHs R2(114) Br CI

4377. CHs R2(116) Br F 4412. CHs R2(115) Br CI

4378. CHs R2(117) Br F 4413. CHs R2(116) Br CI

4379. CHs R2(118) Br F 4414. CHs R2(117) Br CI

4380. CHs R2(119) Br F 4415. CHs R2(118) Br CI

4381. CHs R2(120) Br F 4416. CHs R2(119) Br CI

4382. CHs R2(121) Br F 4417. CHs R2(120) Br CI

4383. CHs R2(122) Br F 4418. CHs R2(121) Br CI

4384. CHs R2(123) Br F 4419. CHs R2(122) Br CI

4385. CHs R2(124) Br F 4420. CHs R2(123) Br CI No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

4421. CHs R2(124) Br CI 4456. CHs R2(123) I F

4422. CHs R2(125) Br CI 4457. CHs R2(124) I F

4423. CHs R2(126) Br CI 4458. CHs R2(125) I F

4424. CHs R2(127) Br CI 4459. CHs R2(126) I F

4425. CHs R2(128) Br CI 4460. CHs R2(127) I F

4426. CHs R2(129) Br CI 4461. CHs R2(128) I F

4427. CHs R2(130) Br CI 4462. CHs R2(129) I F

4428. CHs R2(131) Br CI 4463. CHs R2(130) I F

4429. CHs R2(96) I F 4464. CHs R2(131) I F

4430. CHs R2(97) I F 4465. CHs R2(96) I CI

4431. CHs R2(98) I F 4466. CHs R2(97) I CI

4432. CHs R2(99) I F 4467. CHs R2(98) I CI

4433. CHs R2(100) I F 4468. CHs R2(99) I CI

4434. CHs R2(101) I F 4469. CHs R2(100) I CI

4435. CHs R2(102) I F 4470. CHs R2(101) I CI

4436. CHs R2(103) I F 4471. CHs R2(102) I CI

4437. CHs R2(104) I F 4472. CHs R2(103) I CI

4438. CHs R2(105) I F 4473. CHs R2(104) I CI

4439. CHs R2(106) I F 4474. CHs R2(105) I CI

4440. CHs R2(107) I F 4475. CHs R2(106) I CI

4441. CHs R2(108) I F 4476. CHs R2(107) I CI

4442. CHs R2(109) I F 4477. CHs R2(108) I CI

4443. CHs R2(110) I F 4478. CHs R2(109) I CI

4444. CHs R2(111) I F 4479. CHs R2(110) I CI

4445. CHs R2(112) I F 4480. CHs R²(111) I CI

4446. CHs R2(113) I F 4481. CHs R2(112) I CI

4447. CHs R2(114) I F 4482. CHs R2(113) I CI

4448. CHs R2(115) I F 4483. CHs R2(114) I CI

4449. CHs R2(116) I F 4484. CHs R2(115) I CI

4450. CHs R2(117) I F 4485. CHs R2(116) I CI

4451. CHs R2(118) I F 4486. CHs R2(117) I CI

4452. CHs R2(119) I F 4487. CHs R2(118) I CI

4453. CHs R2(120) I F 4488. CHs R2(119) I CI

4454. CHs R2(121) I F 4489. CHs R2(120) I CI

4455. CHs R2(122) I F 4490. CHs R2(121) I CI No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

4491. CHs R2(122) I CI 4526. CHs R2(121) CFs F

4492. CHs R2(123) I CI 4527. CHs R2(122) CFs F

4493. CHs R2(124) I CI 4528. CHs R2(123) CFs F

4494. CHs R2(125) I CI 4529. CHs R2(124) CFs F

4495. CHs R2(126) I CI 4530. CHs R2(125) CFs F

4496. CHs R2(127) I CI 4531. CHs R2(126) CFs F

4497. CHs R2(128) I CI 4532. CHs R2(127) CFs F

4498. CHs R2(129) I CI 4533. CHs R2(128) CFs F

4499. CHs R2(130) I CI 4534. CHs R2(129) CFs F

4500. CHs R2(131) I CI 4535. CHs R2(130) CFs F

4501. CHs R2(96) CFs F 4536. CHs R2(131) CFs F

4502. CHs R2(97) CFs F 4537. CHs R2(96) CFs CI

4503. CHs R2(98) CFs F 4538. CHs R2(97) CFs CI

4504. CHs R2(99) CFs F 4539. CHs R2(98) CFs CI

4505. CHs R2(100) CFs F 4540. CHs R2(99) CFs CI

4506. CHs R2(101) CFs F 4541. CHs R2(100) CFs CI

4507. CHs R2(102) CFs F 4542. CHs R2(101) CFs CI

4508. CHs R2(103) CFs F 4543. CHs R2(102) CFs CI

4509. CHs R2(104) CFs F 4544. CHs R2(103) CFs CI

4510. CHs R2(105) CFs F 4545. CHs R2(104) CFs CI

4511. CHs R2(106) CFs F 4546. CHs R2(105) CFs CI

4512. CHs R2(107) CFs F 4547. CHs R2(106) CFs CI

4513. CHs R2(108) CFs F 4548. CHs R2(107) CFs CI

4514. CHs R2(109) CFs F 4549. CHs R2(108) CFs CI

4515. CHs R2(110) CFs F 4550. CHs R2(109) CFs CI

4516. CHs R2(111) CFs F 4551. CHs R2(110) CFs CI

4517. CHs R2(112) CFs F 4552. CHs R²(111) CFs CI

4518. CHs R2(113) CFs F 4553. CHs R2(112) CFs CI

4519. CHs R2(114) CFs F 4554. CHs R2(113) CFs CI

4520. CHs R2(115) CFs F 4555. CHs R2(114) CFs CI

4521. CHs R2(116) CFs F 4556. CHs R2(115) CFs CI

4522. CHs R2(117) CFs F 4557. CHs R2(116) CFs CI

4523. CHs R2(118) CFs F 4558. CHs R2(117) CFs CI

4524. CHs R2(119) CFs F 4559. CHs R2(118) CFs CI

4525. CHs R2(120) CFs F 4560. CHs R2(119) CFs CI No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

4561 . CHs R2(120) CFs CI 4596. CHs R2(1 19) SCHs F

4562. CHs R2(121 ) CFs CI 4597. CHs R2(120) SCHs F

4563. CHs R2(122) CFs CI 4598. CHs R2(121 ) SCHs F

4564. CHs R2(123) CFs CI 4599. CHs R2(122) SCHs F

4565. CHs R2(124) CFs CI 4600. CHs R2(123) SCHs F

4566. CHs R2(125) CFs CI 4601 . CHs R2(124) SCHs F

4567. CHs R2(126) CFs CI 4602. CHs R2(125) SCHs F

4568. CHs R2(127) CFs CI 4603. CHs R2(126) SCHs F

4569. CHs R2(128) CFs CI 4604. CHs R2(127) SCHs F

4570. CHs R2(129) CFs CI 4605. CHs R2(128) SCHs F

4571 . CHs R2(130) CFs CI 4606. CHs R2(129) SCHs F

4572. CHs R2(131 ) CFs CI 4607. CHs R2(130) SCHs F

4573. CHs R2(96) SCHs F 4608. CHs R2(131 ) SCHs F

4574. CHs R2(97) SCHs F 4609. CHs R2(96) SCHs CI

4575. CHs R2(98) SCHs F 4610. CHs R2(97) SCHs CI

4576. CHs R2(99) SCHs F 461 1 . CHs R2(98) SCHs CI

4577. CHs R2(100) SCHs F 4612. CHs R2(99) SCHs CI

4578. CHs R2(101 ) SCHs F 4613. CHs R2(100) SCHs CI

4579. CHs R2(102) SCHs F 4614. CHs R2(101 ) SCHs CI

4580. CHs R2(103) SCHs F 4615. CHs R2(102) SCHs CI

4581 . CHs R2(104) SCHs F 4616. CHs R2(103) SCHs CI

4582. CHs R2(105) SCHs F 4617. CHs R2(104) SCHs CI

4583. CHs R2(106) SCHs F 4618. CHs R2(105) SCHs CI

4584. CHs R2(107) SCHs F 4619. CHs R2(106) SCHs CI

4585. CHs R2(108) SCHs F 4620. CHs R2(107) SCHs CI

4586. CHs R2(109) SCHs F 4621 . CHs R2(108) SCHs CI

4587. CHs R2(1 10) SCHs F 4622. CHs R2(109) SCHs CI

4588. CHs R2(1 1 1 ) SCHs F 4623. CHs R2(1 10) SCHs CI

4589. CHs R2(1 12) SCHs F 4624. CHs R²(1 1 1 ) SCHs CI

4590. CHs R2(1 13) SCHs F 4625. CHs R2(1 12) SCHs CI

4591 . CHs R2(1 14) SCHs F 4626. CHs R2(1 13) SCHs CI

4592. CHs R2(1 15) SCHs F 4627. CHs R2(1 14) SCHs CI

4593. CHs R2(1 16) SCHs F 4628. CHs R2(1 15) SCHs CI

4594. CHs R2(1 17) SCHs F 4629. CHs R2(1 16) SCHs CI

4595. CHs R2(1 18) SCHs F 4630. CHs R2(1 17) SCHs CI No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

4631 . CHs R2(1 18) SCHs CI 4666. CHs R2(1 17) S(0)₂CHs F

4632. CHs R2(1 19) SCHs CI 4667. CHs R2(1 18) S(0)₂CHs F

4633. CHs R2(120) SCHs CI 4668. CHs R2(1 19) S(0)₂CHs F

4634. CHs R2(121 ) SCHs CI 4669. CHs R2(120) S(0)₂CHs F

4635. CHs R2(122) SCHs CI 4670. CHs R2(121 ) S(0)₂CHs F

4636. CHs R2(123) SCHs CI 4671 . CHs R2(122) S(0)₂CHs F

4637. CHs R2(124) SCHs CI 4672. CHs R2(123) S(0)₂CHs F

4638. CHs R2(125) SCHs CI 4673. CHs R2(124) S(0)₂CHs F

4639. CHs R2(126) SCHs CI 4674. CHs R2(125) S(0)₂CHs F

4640. CHs R2(127) SCHs CI 4675. CHs R2(126) S(0)₂CHs F

4641 . CHs R2(128) SCHs CI 4676. CHs R2(127) S(0)₂CHs F

4642. CHs R2(129) SCHs CI 4677. CHs R2(128) S(0)₂CHs F

4643. CHs R2(130) SCHs CI 4678. CHs R2(129) S(0)₂CHs F

4644. CHs R2(131 ) SCHs CI 4679. CHs R2(130) S(0)₂CHs F

4645. CHs R2(96) S(0)₂CHs F 4680. CHs R2(131 ) S(0)₂CHs F

4646. CHs R2(97) S(0)₂CHs F 4681 . CHs R2(96) S(0)₂CHs CI

4647. CHs R2(98) S(0)₂CHs F 4682. CHs R2(97) S(0)₂CHs CI

4648. CHs R2(99) S(0)₂CHs F 4683. CHs R2(98) S(0)₂CHs CI

4649. CHs R2(100) S(0)₂CHs F 4684. CHs R2(99) S(0)₂CHs CI

4650. CHs R2(101 ) S(0)₂CHs F 4685. CHs R2(100) S(0)₂CHs CI

4651 . CHs R2(102) S(0)₂CHs F 4686. CHs R2(101 ) S(0)₂CHs CI

4652. CHs R2(103) S(0)₂CHs F 4687. CHs R2(102) S(0)₂CHs CI

4653. CHs R2(104) S(0)₂CHs F 4688. CHs R2(103) S(0)₂CHs CI

4654. CHs R2(105) S(0)₂CHs F 4689. CHs R2(104) S(0)₂CHs CI

4655. CHs R2(106) S(0)₂CHs F 4690. CHs R2(105) S(0)₂CHs CI

4656. CHs R2(107) S(0)₂CHs F 4691 . CHs R2(106) S(0)₂CHs CI

4657. CHs R2(108) S(0)₂CHs F 4692. CHs R2(107) S(0)₂CHs CI

4658. CHs R2(109) S(0)₂CHs F 4693. CHs R2(108) S(0)₂CHs CI

4659. CHs R2(1 10) S(0)₂CHs F 4694. CHs R2(109) S(0)₂CHs CI

4660. CHs R2(1 1 1 ) S(0)₂CHs F 4695. CHs R2(1 10) S(0)₂CHs CI

4661 . CHs R2(1 12) S(0)₂CHs F 4696. CHs R²(1 1 1 ) S(0)₂CHs CI

4662. CHs R2(1 13) S(0)₂CHs F 4697. CHs R2(1 12) S(0)₂CHs CI

4663. CHs R2(1 14) S(0)₂CHs F 4698. CHs R2(1 13) S(0)₂CHs CI

4664. CHs R2(1 15) S(0)₂CHs F 4699. CHs R2(1 14) S(0)₂CHs CI

4665. CHs R2(1 16) S(0)₂CHs F 4700. CHs R2(1 15) S(0)₂CHs CI No. R¹ R2 R³ R⁵ No. R¹ R2 R³ R⁵

4701 . CHs R2(1 16) S(0)₂CHs CI 4709. CHs R2(124) S(0)₂CHs CI

4702. CHs R2(1 17) S(0)₂CHs CI 4710. CHs R2(125) S(0)₂CHs CI

4703. CHs R2(1 18) S(0)₂CHs CI 471 1 . CHs R2(126) S(0)₂CHs CI

4704. CHs R2(1 19) S(0)₂CHs CI 4712. CHs R2(127) S(0)₂CHs CI

4705. CHs R2(120) S(0)₂CHs CI 4713. CHs R2(128) S(0)₂CHs CI

4706. CHs R2(121 ) S(0)₂CHs CI 4714. CHs R2(129) S(0)₂CHs CI

4707. CHs R2(122) S(0)₂CHs CI 4715. CHs R2(130) S(0)₂CHs CI

4708. CHs R2(123) S(0)₂CHs CI 4716. CHs R2(131 ) S(0)₂CHs CI

Table A-1 : Definitions of substituents ) to R2(95); arrows indicate the attachment to the oxygen atom.

R²(61 ) R²(71 )

R²(62) R²(72)

R²(63) R²(73)

R²(64) R²(74)

R²(65) R²(75)

R²(66)

R²(76)

R²(67)

R²(77)

R²(68)

R²(69)

R²(79)

R²(70)

R²(80)

According to a particularly preferred embodiment of the invention the compounds of the formula I are selected from compounds of formula I. A, the N-oxides and the agriculturally suita- ble salts thereof:

where R^6a is H, methyl, ethyl or n-propyl, in particular methyl, R⁴ is hydrogen, CI or F, in particular hydrogen, R⁵ is halogen, CHF2 or CF3, in particular F, and the combination of R¹, R² and R³ is as given in lines 1 to 121 of the following table I.A, where in case that R^6a is H, the combination of R¹, R² and R³ is in particular as given in lines 4 and 20 of the following table I.A, and where in case that R^6a is ethyl or n-propyl, the combination of R¹, R² and R³ is in particular as given in line 4 of the following table I.A the compounds of the formula (I.B), the N-oxides and the agriculturally suitable salts thereof:

where R^6b or ethyl, in particular methyl, R⁴ is hydrogen, CI or F, in particular hydrogen, R⁵ is halogen, CHF2 or CF3, in particular F, and the combination of R¹, R² and R³ is as given in lines 1 to 4 of the following table I.B, the compounds of the formula (I.C), the N-oxides and the agriculturally suitable salts thereof:

where the combination of R¹, R² and R³ is as given in line 4 of the following table I.A; and the compounds of the formula (I.D), the N-oxides and the agriculturally suitable salts

where the combination of R¹, R² and R³ is as given in line 4 of the following table I.A; where in tables I.A and I.B the arrow indicates the point of attachment of R² to the oxygen atom in formulae I.A and I.B, respectively:

Table I.A

Table I.B

The compounds of formula I can be prepared by standard methods of organic chemistry, e.g. by the methods described in the schemes 1 to 15 below. The substituents, variables and indices used in the schemes 1 to 15 are as defined above for the compounds of formula I, if not specified otherwise.

The compounds of formula I can be prepared for instance as shown in Scheme 1 below.

Scheme

Phenolic benzamide compounds of formula II can be reacted with compounds R²-X to afford compounds of the formula I. X is a suitable leaving group, such as halogen, in particular CI. 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 or potassium 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 apro- tic solvents such as pentane, hexane, heptane, octane, cyclohexane, dichloromethane, chloro- form, 1 ,2-dichlorethane, benzene, chlorobenzene, toluene, the xylenes, dichlorobenzene, trime- thylbenzene, 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 re- acted with one another in equimolar or nearly equimolar amounts at a reaction temperature usually in the range of -20°C to 120°C and preferably in the range of 0°C to 70°C.

Alternatively, compounds of formula I can also be prepared as shown in Scheme 2. Reaction of an amine of formula III with a benzoic acid derivative of formula IV yields compound I. The reaction is preferably carried out in the presence of a suitable activating agent, which converts the acid group of compound VI 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 employed. The activated ester or amide can be formed, depending in particular on the specific activating agent used, either in situ by contacting compound V with the activating agent in the presence of compound III or IV, or in a separate step prior to the reaction with compound III or IV. 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), nitrophenol, 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 III 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 dichloroethane, ethers, e.g. tetrahydrofuran or 1 ,4-dioxane or carboxamides, e.g. N,N-dimethylformamide, Ν,Ν-dimethylacetamide or N- methylpyrrolidone. The reaction is ordinarily carried out at temperatures in the range from -20°C to +25°C.

Instead of converting the acid group of compound IV into an activated ester or amide it can also be converted into an acid halide, preferably an acid choride, either in situ or in a separate reaction, via reaction with a suitable chlorination reagent, such as oxalyl chloride or thionyl chloride. The acid halide derivative of the compound of formula IV obtained this way can then be reacted with a metal amide derived from the amine of formula III to afford the acid amide of formula I. The metal amide is typically prepared by reacting the amine of formula III with methyl lithium in one of the aforementioned inert solvents, such as e.g. THF, at temperatures in the range of -100°C to 5°C. The conversion of the acid halide derivative with the metal amide is also carried out in one of said inert solvents, such as in particular THF, at initial temperatures of be- tween-100°C to -50°C to final temperatures of between -20°C to 10°C. Scheme 2:

The compounds of formula I with R² being a radical of the formula 2a wherein Z² is a bond, are compounds of the formula l-2a' which can be prepared for instance as shown in Scheme 3 below.

Scheme

Phenolic benzamide compounds of formula II may be converted with phosgene to the corresponding chloroformate which can subsequently be reacted with the amine of formula V to give the desired benzamide carbamate of formula l-2a'. Typically, for both reaction steps 1 ) and 2) invert solvents are used. Both reaction steps are usually carried out at temperatures of about -50°C to 30°C in the presence of a base, such as a tertary amine, e.g. trimethylamine, or pyridine.

The compounds of formula l-2a' can also be prepared according procedures described in via the synthetic route depicted in Scheme 4 below, using procedures of T. Patonay et al., Synth. Commun. 1990, 20, 2865-2885.

Scheme 4:

Conversion of a chloromethyl carbonate of formula VI with an amine of fomula V results in the benzamide carbamate of formula l-2a'. The reaction is usually carried out in an inert solvent, such as benzene, using the amine V in excess, particularly in an amount of about two molar equivalents. Additionally, a co-base, such as pyridine, may be employed. The reaction temperature is typically in the range of 10°C to 150°C. The chloromethyl carbonates VI used in this reac- tion are readily available by treating chloromethyl chloroformate with the phenolic benzamide compound of formula II in the presence of a base, e.g. triethylamine. Alternatively, the compounds of formula I-2 a' can be prepared according to procedures described by G. Barcelo et al., Synthesis 1986, 627-632, as depicted in Scheme 5.

Scheme 5:

R⁷= CH₃ or CCh

1 -Chloromethyl carbonates of the formula VII can be reacted with amines of formula V to afford the corresponding benzamide carbamate of formula l-2a'. The reaction is generally run in tetrahydrofuran or dioxane in the presence of a base, such as in particular an aqueous solution of potassium carbonate, at a temperature of about -10°C to 40°C. The educt of formula VII can be obtained by treating the corresponding 1 -chloroalkyl chloroformate with a phenolic benzamide compound of formula II in the presence of a base, such as in particular pyridine.

The compounds of formula I-2 a' with R^2a or R^2b being hydrogen can also be prepared as shown in Scheme 6 below. Sche

Phenolic benzamide compounds of formula II may be converted with isocyanates of formula VIII to the benzamide carbamate of the formula IX, which is a compound of formula l-2a', wherein either R^2a or R^2b is hydrogen. The reaction is generally carried out in an invert solvent with a suitable base, e.g. triethylamine, being present.

As shown in Scheme 7, the phenolic benzamide compounds of formula II can be prepared using a synthesis route that includes the intermediate protection of the hydroxyl group.

Scheme 7:

In step 1 ) the hydroxyl group of the phenol derivative of formula X is protected by introducing a suitable protective group, such as in particular a benzyl group. This conversion is typically achieved via reaction with a benzyl halide, such as in particular benzyl bromide, in the presence of a base. Suitable bases are for example carbonates, such as in particular potassium carbonate. The reaction can be carried out in an aprotic solvent, such as acetone, at a temperature in the range of about 0°C to 100°C.

In step 2) the benzyl protected compound obtained in step 1 ) is first treated with a strong base, in particular an organolithium base, such as n-butyllithium or lithium diisopropylamide, and afterwards reacted with carbon dioxide to afford to benzoic acid derivative of formula XI. Suitable solvents are inert ones, such as in particular THF. The reaction is started at a temperature in the range of -100°C to -50°C and concluded at about -10°C to 30°C.

In step 3) the benzoic acid derivative of formula XI is activated by conversion to a suitable ester or amide, or preferably to a suitable acid halide, by analogy with the synthesis described in Scheme 2.

In step 4) the activated benzoic acid derivative of formula XII obtained in step 3) is ami- dated with an amine of formula III by analogy with the synthesis described in Scheme 2. Accordingly, steps 3) and 4) may also be carried in situ or even simultaneously.

The removal of the protecting group is achieved in step 5), in case PG is a benzyl group, for instance by subjecting the amidation product obtained in step 4) to strong acidic conditions to afford the phenolic benzamide of formula II.

Scheme 8 depicts a synthetic route towards compounds of the formula IV with R² being a radical of the formula 2a wherein Z² is dimethylmethylene bridge (-C(CH3)2-). These compounds are of the formula IV shown below and may serve as precursor for compounds of the formula I having the same substituent R².

Scheme 8:

The Bargellini reaction can be used in step 1 ) to convert the phenol derivative of formula X into a compound of formula XIII by reacting it with acetone and chloroform in the presence of a base, e.g. an alkali metal hydroxide, such as sodium hydroxide, at a temperature in the range of 10°C to 80°C. Acetone typically also serves as solvent and is therefore used in excess.

The amidation in step 2) can be accomplished, for instance, by converting the compound of formula XIII, by analogy with the reaction described in Scheme 2, into the corresponding acid halide, which is then treated with the amine of formula V to afford a compound of formula XIV.

The carboxylation in step 3) can be carried out analogous to the reaction shown in Scheme 3 to yield the benzoic acid derivative of formula IV, which is a useful intermediate to prepare a corresponding benzamide of the formula I via the reaction described in Scheme 2.

The the phenol derivatives of the formula X and the benzoic acid derivatives of formula IV are either commercially available or are obtainable according to methods known from the literature. This holds also true for the amines Q-Nhb of the formula III, wherein the substituents R^6a, R^6b, R^6c, or R^6d are, for instance, hydrogen or an alkyl. For example, 5-amino-1 -R^6a-tetrazole of formula lll-a, with R^6a being alkyl, can be prepared from 5-aminotetrazole according to the method described in the Journal of the American Chemical Society, 1954, 76, 923-924 (Scheme 9).

Scheme 9:

(lll-a)

Alternatively, 5-amino-1 -R^6a -tetrazole compounds of formula lll-a can be prepared according to the method described in the Journal of the American Chemical Society, 1954, 76, 88- 89 (Scheme 10).

Scheme 10:

(lll-a)

5-amino-1 -R^6b -triazoles of formula lll-b are either commercially available or are obtainable according to methods described in the literature. As shown in Scheme 1 1 , 5-amino-1 -R^6b- triazole can for example be prepared from 5-aminotriazole according to the method described in Zeitschrift fur Chemie, 1990, 30, 12, 436-437.

Scheme 1 1 :

(Ill-b)

Alternatively, 5-amino-1 -R^6b-triazole compounds of formula lll-b, can also be prepared analogous to the synthesis described in Chemische Berichte, 1964, 97, 2, 396-404, as shown in Scheme 12.

Scheme 12:

(lll-b)

The 4-amino-1 ,2,5-oxadiazole compounds of the formula lll-c are either commercially available or are obtainable according to methods known from the literature. For example, 3- alkyl-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), as depicted in Scheme 13.

Scheme 13:

(lll-c)

As shown in Scheme 14, the compounds of the formula lll-c, where R^6c 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 disclosed in Heteroatom Chemistry, 15(3), 199-207 (2004).

Scheme 14:

(lll-c)

As shown in Scheme 15, the compounds of the formula lll-c, where R^6c is a nucleophilic residue, can be prepared by introducing the nucleophilic residue via the substitution of a leaving group L, e.g. halogene, in the 4-position of the 1 ,2,5-oxadiazoles compounds of formula XV in accordance to precedures disclosed, for example, 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). Scheme 15:

(XV) (lll-c)

In addition, compounds of formulae lll-a, lll-b and lll-c can be obtained by purchase or can be prepared by processes known in the art or disclosed in the literature, e.g. in WO

9746530, WO 9831676, WO 9831681 , WO 2002/018352, WO 2000/003988, US 2007/0191335, US 6277847.

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 recrystalliza- tion 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 composi- tions comprising the compound I, 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 caro- ta, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arbo- reum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usi- tatissimum, Lycopersicon lycopersicum, Malus spec, Manihot esculenta, Medicago sativa, Mu- sa 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 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, US 5,013,659) or imidazolinones (see, for example, US 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, glypho- sate (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, US 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 tol- erant 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 hy- droxyphenyl pyruvate dioxygenase (mutated HPPD)" refers to the replacement of an amino acid of the wild-type primary sequences SEQ ID NO: 2, 5, 8, 1 1 , 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 vari- ant, 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 etal., Eur.J.Biochem., 205, 459-466, 1992, W096/38567), of plants such as Arabidopsis (W096/38567, Genebank

AF047834) or of carrot (W096/38567, Genebank 87257), of Coccicoides (Genebank COITRP), HPPDs of Brassica, cotton, Synechocystis, and tomato (US 7,297,541 ), of mammals such as the mouse or the pig. Furthermore, artificial HPPD sequences have been described, for exam- pie in US6,768,044; US6,268,549;

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 pre- sent 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 occur- ring 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, 1 1 , 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, 1 1 , 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 availa- ble 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 un- branched 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 en- zymes 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, lacZ, CMP (cal- modulin-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 a -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 ex- ample Creighton (1984) Proteins. W.H. Freeman and Company (Eds).

Amino acid substitutions, deletions and/or insertions may readily be made using peptide syn- thetic 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, OH), QuikChange Site Directed mutagenesis (Stratagene, San Diego, CA), 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 inter- est, 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. Fur- thermore, "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 Ter- pe, 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 homo- logues, 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., pp53-61 , AAAI Press, Menlo Park; Hulo et al., Nucl. Acids. Res. 32:D134-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 Needle- man 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 TF, Waterman MS (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, 1 1 , 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 activitiy 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 em- bodiment the mutated HPPD useful for the present invention comprises a sequence of SEQ ID NO: 2, 5, 8, 1 1 , 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 homo- logue 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 de- veloped, 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 ami- no 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 4a. Table 4a: (Sequence ID No: 2): single amino acid substitutions

Key amino acid position Substituents

Val212 lie, Leu

Val213 Thr, Ala

Asn215 Ala, His

Ala236 Leu, Ser, Arg

Phe238 Val, Ala

Leu250 Val, Met

Ser252 Thr

Pro265 Ala

Asn267 Tyr, Gin

Gln278 His, Asn, Ser

Ile279 Thr

Arg309 Lys, Ala

Leu320 Asn, Gin, His, Tyr,

Pro321 Ala, Arg, Gly, Asn

Leu334 Glu, Cys

Leu353 Met, Tyr, Ala, Ser

Phe366 lie, Leu, Tyr

Gly371 lie, Phe

Thr375 Pro Key amino acid position Substituents

Phe377 Ala, Leu, Ser

Gly403 Arg

Phe404 Leu, Pro

Lys406 Thr

Gly407 Cys, His

Phe409 lie, His

Glu41 1 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 4b. Table 4b: (with reference to Sequence ID No: 2): combined amino acid substitutions

Combination No Key amino acid position and and its substitutents

1 A236L, E41 1 T

2 L320H, P321A

3 L320H, P321 R

4 L320N, P321A

5 L320N, P321 R

6 L320Q, P321A

7 L320Q, P321 R

8 L320Y, P321A

9 L320Y, P321 R

10 L353M, P321 R

1 1 L353M, P321 R, A236L

12 L353M, P321 R, A236L, E41 1T

13 L353M, P321 R, E41 1T

14 L353M, P321 R, L320H

15 L353M, P321 R, L320N

16 L353M, P321 R, L320Q

17 L353M, P321 R, L320Y Combination No Key amino acid position and and its substitutents

18 L353M, P321 R, V212I

19 L353M, P321 R, V212I, L334E

20 L353M, P321 R, V212L, L334E

21 L353M, P321 R, V212L, L334E, A236L

22 L353M, P321 R, V212L, L334E, A236L, E41 1 T

23 L353M, P321 R, V212L, L334E, E41 1 T

24 L353M, P321 R, V212L, L334E, L320H

25 L353M, P321 R, V212L, L334E, L320N

26 L353M, P321 R, V212L, L334E, L320Q

27 L353M, P321 R, 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 polypeptide 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 4c.

Table 4c: (Sequence ID No: 53): single amino acid substitutions

Key amino acid position Substituents Preferred 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 Key amino acid position Substituents Preferred substituents

Ser267 Thr Thr

Pro280 Ala Ala

Asn282 Tyr, Gin Tyr, Gin

Lys291 Arg, Ala Arg

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

Ile294 Thr Thr

Arg324 Lys, Ala Lys, Ala

Met335 Ala, Trp, Phe, Leu, lie, Val, Asn, Gin, Gin, 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 Gin Gin

Leu368 Met, Tyr, Met

Phe381 lie, Leu, Tyr lie, Leu

Leu385 Ala, Val, Gin, Asp Val, Asp

Gly386 lie, Phe lie, 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 lie, His lie, 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 pa- ralogue thereof, wherein two, three, four or five key amino acids are substituted by another ami- no acid residue. Particularly preferred double, triple, quadruple, or quintuple mutations are described in Table 4d.

Table 4d: (reference to Sequence ID No: 53): combined amino acid substitutions

Combination Key amino acid Substituents Preferred substi¬

No position tuents Combination Key amino acid Substituents Preferred substi¬

No position tuents

1 Pro336 Ala, Arg Ala

Glu363 Gin Gin

2 Pro336 Ala, Arg Ala

Glu363 Gin Gin

Leu385 Ala, Val Val

3 Pro336 Ala, Arg Ala

Glu363 Gin Gin

Leu385 Ala, Val Val

Ile393 Ala, Leu Leu

4 Leu385 Ala, Val Val

Ile393 Ala, Leu Leu

5 Met335 Ala, Trp, Phe, Leu, lie, Val, Asn, Gin, Gin, Asn, His, Tyr

His, Tyr, Ser, Thr, Cys

Pro336 Ala, Arg, Gly Ala, Gly

6 Met335 Ala, Trp, Phe, Leu, lie, Val, Asn, Gin, Gin, Asn, His, Tyr

His, Tyr, Ser, Thr, Cys

Pro336 Ala, Arg, Gly Ala, Gly

Glu363 Gin Gin

7 Met335 Ala, Trp, Phe, Leu, lie, Val, Asn, Gin, Gin, Asn, His,

His, Tyr, Ser, Thr, Cys Tyr, Leu

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 posi- tion 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 lie, 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 lie, 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 oth- er 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.

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.

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.

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

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 Gin, and the amino acid corresponding to or at position 341 is lie.

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

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

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

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

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

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, Gin, Glu, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.

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

the amino acid corresponding to or at position 405 is Ala, Arg, Asn, Asp, Cys, Gin, 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 251 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, or Tyr, particularly preferred Ala.

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

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

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

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

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.

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

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 Gin.

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 Gin.

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

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, Gin, Glu, Gly, His, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val, particularly preferred Val.

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

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, Gin, Glu, Gly, His, lie, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.

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

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

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

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

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, Gin, Glu, Gly, His, lie, Leu, Lys, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.

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

the amino acid corresponding to or at position 212 is Ala, Arg, Asp, Cys, Gin, Glu, Gly, 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 223 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, or Tyr.

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

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, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.

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

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

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

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

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, Gin, Glu, Gly, His, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.

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

the amino acid corresponding to or at position 410 is Ala, Arg, Asn, Asp, Cys, Gin, 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 412 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Pro, Ser, Thr, Trp, Tyr, or Val.

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

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, Gin, Gly, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.

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

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

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

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.

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 of SEQ ID NO: 2, 5, 8, 1 1 , 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 4a and 4b, 4c, and 4d can be chosen to be substituted by any other amino acid by conserved amino acids, and more preferably by the amino acids of tables 4a and 4b, 4c, and 4d.

Numerous crop plants, for example Clearfield® oilseed rape, tolerant to imidazolinones, for example imazamox, have been generated with the aid of classic breeding methods (mutagenesis). Crop plants such as soybeans, cotton, corn, beet and oilseed rape, resistant to glyphosate or glufosinate, which are available under the tradenames RoundupReady^® (glypho- sate) 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 CrylAb, CrylAc, Cry1 F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 , Cry9c, Cry34Ab1 or Cry35Ab1 ; or vegetative insec- ticidal proteins (VIPs), for example VIP1 , VIP2, VIP3, or VIP3A; insecticidal proteins of nema- tode-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 Strep- tomycetes; 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 nema- todes (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 CrylAb), YieldGard^® Plus (corn varieties which produce the toxins CrylAb 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 CrylAc), Bollgard^® I (cotton varieties which produce the toxin CrylAc), Bollgard^® II (cotton varieties which produce the toxins CrylAc and Cry2Ab2); VIPCOT^® (cotton varieties which produce a VIP toxin); NewLeaf^® (potato varieties which produce the toxin Cry3A); Bt-Xtra^®, NatureGard^®, KnockOut^®, BiteGard^®, Protecta^®, Bt1 1 (for example Agrisure^® CB) and Bt176 from Syngenta Seeds SAS, France (corn varieties which produce the toxin CrylAb and the PAT enyzme), 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 pro- duce a modified version of the toxin CrylAc) and 1507 from Pioneer Overseas Corporation, Belgium (corn varieties which produce the toxin Cry1 F 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 im- proved 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 monounsatu- rated 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 in- creasing 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.

In a specific embodiment, the compounds according to the invention, the N-oxides or agriculturally suitable salts thereof are used for controlling at least one of the following undesired plants: Alopecurus myosuroiedes, Echinocloa crus-galli, Amaranthus retroflexus, Chenopodium album.

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 1 12 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 1 12, 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 la, 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 cyclohexa- none 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 or- ganic 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 multilayer 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, tu- bers, 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 saf- eners. Safeners are chemical compounds which prevent or reduce 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-1 H-

1 ,2,4-triazole-3-carboxylic acids, 1 -phenyl-4,5-dihydro-5-alkyl-1 A pyrazole-S^-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 herbicidal or growth-regulating groups of active compounds or 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/heteroaryloxyalkanoic 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, chloroacetanilides, cyclohexenone oxime ether derivates, diazines, dichloropropionic acid and its derivatives, dihydrobenzofurans, dihydrofu- ran-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 heteroaryloxyphenoxypro- pionic esters, phenylacetic acid and its derivatives, 2-phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic 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 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 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, cy- cloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, halox- yfop, 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, 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, ima- zethapyr, 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, pyrimi- nobac-methyl, pyrithiobac, pyrithiobac-sodium, pyroxsulam, rimsulfuron, sulfometuron, sulfome- turon-methyl, sulfosulfuron, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfu- ron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron, triflusulfu- ron-methyl and tritosulfuron;

b3) from the group of the photosynthesis inhibitors:

ametryn, amicarbazone, atrazine, bentazone, bentazone-sodium, bromacil, bromofenox- im, 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, me- toxuron, metribuzin, monolinuron, neburon, paraquat, paraquat-dichloride, paraquat- dimetilsulfate, pentanochlor, phenmedipham, phenmedipham-ethyl, prometon, prometryn, pro- panil, propazine, pyridafol, pyridate, siduron, simazine, simetryn, tebuthiuron, terbacil, ter- bumeton, terbuthylazine, terbutryn, thidiazuron and trietazine;

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

acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, bu- tafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluorogly- cofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraf I uf en-ethyl, saflufenacil, sulfen- trazone, 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-1 pyrazole-1 -carboxamide (H-3; CAS 452098-92-9),

N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1 A pyrazole-l - carboxamide (H-4; CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5- methyl-1 pyrazole-1 -carboxamide (H-5; CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6- fluoro-4-trifluoromethylphenoxy)-5-methyl-1 A pyrazole-l -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, 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, 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 and 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)-1 H-pyrimidine-2,4-dione;

b5) from the group of the bleacher herbicides:

aclonifen, amitrol, beflubutamid, benzobicyclon, benzofenap, clomazone, diflufenican, flu- ridone, flurochloridone, flurtamone, isoxaflutole, mesotrione, norflurazon, picolinafen, pyrasulfu- tole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, 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) and 4-(3-trifluoromethylphenoxy)-2-(4- trifluoromethylphenyl)pyrimidine (H-8; CAS 180608-33-7);

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, chlor- propham, 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, dime- thenamid-P, diphenamid, fentrazamide, flufenacet, mefenacet, metazachlor, metolachlor, metolachlor-S, naproanilide, napropamide, pethoxamid, piperophos, pretilachlor, propachlor, propisochlor, pyroxasulfone (KI H-485) and thenylchlor;

Compounds of the formula 2:

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 R^aa; R²¹ ,R²²,R²³,R²⁴ are H, halogen or Ci-C₄-alkyl; X is O or NH; n is 0 or 1 .

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

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

_R2i _{i R}22 _R23 _R24 _{a re H i C! i F or C H3;} R25 j_s halogen, Ci-C₄-alkyl or Ci-C₄-haloalkyl; R²⁶ is Ci-C₄- alkyl; R²⁷ is halogen, Ci-C₄-alkoxy or Ci-C₄-haloalkoxy; R²⁸ is H, halogen, Ci-C₄-alkyl, Ci-C₄- haloalkyl or Ci-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:

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-1 H-pyrazol-4-ylmethane- sulfonyl]-4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole (2-1 ); 3-{[5-(2,2-difluoroethoxy)-1 -methyl-3- trifluoromethyl-1 H-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-trifluorom

[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-1 H-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-trifluo

[1 ,2,3]triazole (2-7); 3-{[5-(2,2-difluoroethoxy)-1 -methyl-3-trifluoromethyl-1 H-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-trifluorome

[1 ,2,3]triazole (2-9);

b1 1 ) 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, 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, and 5,6-dichloro-2-cyclopropyl-4- pyrimidinecarboxylic acid (H-9; CAS 858956-08-8) and its salts and esters;

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, dime- thipin, DSMA, dymron, endothal and its salts, etobenzanid, flamprop, flamprop-isopropyl, flam- prop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol-butyl, flurprimidol, fos- amine, 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, cyprosulfa- mide, dichlormid, dicyclonone, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furi- lazole, isoxadifen, mefenpyr, mephenate, naphthalic anhydride, oxabetrinil, 4-(dichloroacetyl)-1 - oxa-4-azaspiro[4.5]decane (H-1 1 ; 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 97/41 1 16, WO 97/41 1 17, WO 97/41 1 18, WO 01/83459 and WO 2008/074991 and from W. Kramer et al. (ed.) "Modern Crop Protection Compounds", Vol. 1 , Wiley VCH, 2007 and the literature quoted therein.

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, 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 auxilia- ries 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 selected from the active com- pounds 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.

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 compositions B-1 to B-1236 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 compositions described are in each case preferably present in synergistically effective amounts.

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-1 1 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 — Herbicide(s) B Safener C

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 — Herbicide(s) B Safener C

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 atrazine + H-1 —

B-95 atrazine + glyphosate —

B-96 atrazine + mesotrione —

B-97 atrazine + nicosulfuron —

B-98 atrazine + tembotrione —

B-99 atrazine + topramezone —

B-100 clomazone + glyphosate —

B-101 diflufenican + clodinafop-propargyl —

B-102 diflufenican + fenoxaprop-P-ethyl —

B-103 diflufenican + flupyrsulfuron-methyl-sodium —

B-104 diflufenican + glyphosate — Herbicide(s) B Safener C

B-105 diflufenican + mesosulfuron-methyl —

B-106 diflufenican + pinoxaden —

B-107 diflufenican + pyroxsulam —

B-108 flumetsulam + glyphosate —

B-109 flumioxazin + glyphosate —

B-1 10 imazapic + glyphosate —

B-1 1 1 imazethapyr + glyphosate —

B-1 12 isoxaflutol + H-1 —

B-1 13 isoxaflutol + glyphosate —

B-1 14 metazachlor + H-1 —

B-1 15 metazachlor + glyphosate —

B-1 16 metazachlor + mesotrione —

B-1 17 metazachlor + nicosulfuron —

B-1 18 metazachlor + terbuthylazine —

B-1 19 metazachlor + topramezone —

B-120 metribuzin + glyphosate —

B-121 pendimethalin + H-1 —

B-122 pendimethalin + clodinafop-propargyl —

B-123 pendimethalin + fenoxaprop-P-ethyl —

B-124 pendimethalin + flupyrsulfuron-methyl-sodium —

B-125 pendimethalin + glyphosate —

B-126 pendimethalin + mesosulfuron-methyl —

B-127 pendimethalin + mesotrione —

B-128 pendimethalin + nicosulfuron —

B-129 pendimethalin + pinoxaden —

B-130 pendimethalin + pyroxsulam —

B-131 pendimethalin + tembotrione —

B-132 pendimethalin + topramezone —

B-133 pyroxasulfone + tembotrione —

B-134 pyroxasulfone + topramezone —

B-135 sulfentrazone + glyphosate —

B-136 terbuthylazine + H-1 —

B-137 terbuthylazine + foramsulfuron —

B-138 terbuthylazine + glyphosate —

B-139 terbuthylazine + mesotrione —

B-140 terbuthylazine + nicosulfuron —

B-141 terbuthylazine + tembotrione —

B-142 terbuthylazine + topramezone —

B-143 trifluralin + glyphosate — Herbicide(s) B Safener C

B-144 — benoxacor

B-145 — cloquintocet

B-146 — cyprosulfamide

B-147 — dichlormid

B-148 — fenchlorazole

B-149 — isoxadifen

B-150 — mefenpyr

B-151 — H-1 1

B-152 — H-12

B-153 clodinafop-propargyl benoxacor

B-154 cycloxydim benoxacor

B-155 cyhalofop-butyl benoxacor

B-156 fenoxaprop-P-ethyl benoxacor

B-157 pinoxaden benoxacor

B-158 profoxydim benoxacor

B-159 tepraloxydim benoxacor

B-160 tralkoxydim benoxacor

B-161 esprocarb benoxacor

B-162 prosulfocarb benoxacor

B-163 thiobencarb benoxacor

B-164 triallate benoxacor

B-165 bensulfuron-methyl benoxacor

B-166 bispyribac-sodium benoxacor

B-167 cyclosulfamuron benoxacor

B-168 flumetsulam benoxacor

B-169 flupyrsulfuron-methyl-sodium benoxacor

B-170 foramsulfuron benoxacor

B-171 imazamox benoxacor

B-172 imazapic benoxacor

B-173 imazapyr benoxacor

B-174 imazaquin benoxacor

B-175 imazethapyr benoxacor

B-176 imazosulfuron benoxacor

B-177 iodosulfuron-methyl-sodium benoxacor

B-178 mesosulfuron benoxacor

B-179 nicosulfuron benoxacor

B-180 penoxsulam benoxacor

B-181 propoxycarbazone-sodium benoxacor

B-182 pyrazosulfuron-ethyl benoxacor Herbicide(s) B Safener C

B-183 pyroxsulam benoxacor

B-184 rimsulfuron benoxacor

B-185 sulfosulfuron benoxacor

B-186 thiencarbazone-methyl benoxacor

B-187 tritosulfuron benoxacor

B-188 2,4-D and its salts and esters benoxacor

B-189 aminopyralid and its salts and esters benoxacor

B-190 clopyralid and its salts and esters benoxacor

B-191 dicamba and its salts and esters benoxacor

B-192 fluroxypyr-meptyl benoxacor

B-193 quinclorac benoxacor

B-194 quinmerac benoxacor

B-195 H-9 benoxacor

B-196 diflufenzopyr benoxacor

B-197 diflufenzopyr-sodium benoxacor

B-198 clomazone benoxacor

B-199 diflufenican benoxacor

B-200 fluorochloridone benoxacor

B-201 isoxaflutol benoxacor

B-202 mesotrione benoxacor

B-203 picolinafen benoxacor

B-204 sulcotrione benoxacor

B-205 tefuryltrione benoxacor

B-206 tembotrione benoxacor

B-207 topramezone benoxacor

B-208 H-7 benoxacor

B-209 atrazine benoxacor

B-210 diuron benoxacor

B-21 1 fluometuron benoxacor

B-212 hexazinone benoxacor

B-213 isoproturon benoxacor

B-214 metribuzin benoxacor

B-215 propanil benoxacor

B-216 terbuthylazine benoxacor

B-217 paraquat dichloride benoxacor

B-218 flumioxazin benoxacor

B-219 oxyfluorfen benoxacor

B-220 saflufenacil benoxacor

B-221 sulfentrazone benoxacor Herbicide(s) B Safener C

B-222 H-1 benoxacor

B-223 H-2 benoxacor

B-224 glyphosate benoxacor

B-225 glyphosate-isopropylammonium benoxacor

B-226 glyphosate-trimesium (sulfosate) benoxacor

B-227 glufosinate benoxacor

B-228 glufosinate-ammonium benoxacor

B-229 pendimethalin benoxacor

B-230 trifluralin benoxacor

B-231 acetochlor benoxacor

B-232 cafenstrole benoxacor

B-233 dimethenamid-P benoxacor

B-234 fentrazamide benoxacor

B-235 flufenacet benoxacor

B-236 mefenacet benoxacor

B-237 metazachlor benoxacor

B-238 metolachlor-S benoxacor

B-239 pyroxasulfone benoxacor

B-240 isoxaben benoxacor

B-241 dymron benoxacor

B-242 indanofan benoxacor

B-243 oxaziclomefone benoxacor

B-244 triaziflam benoxacor

B-245 atrazine + H-1 benoxacor

B-246 atrazine + glyphosate benoxacor

B-247 atrazine + mesotrione benoxacor

B-248 atrazine + nicosulfuron benoxacor

B-249 atrazine + tembotrione benoxacor

B-250 atrazine + topramezone benoxacor

B-251 clomazone + glyphosate benoxacor

B-252 diflufenican + clodinafop-propargyl benoxacor

B-253 diflufenican + fenoxaprop-P-ethyl benoxacor

B-254 diflufenican + flupyrsulfuron-methyl-sodium benoxacor

B-255 diflufenican + glyphosate benoxacor

B-256 diflufenican + mesosulfuron-methyl benoxacor

B-257 diflufenican + pinoxaden benoxacor

B-258 diflufenican + pyroxsulam benoxacor

B-259 flumetsulam + glyphosate benoxacor

B-260 flumioxazin + glyphosate benoxacor Herbicide(s) B Safener C

B-261 imazapic + glyphosate benoxacor

B-262 imazethapyr + glyphosate benoxacor

B-263 isoxaflutol + H-1 benoxacor

B-264 isoxaflutol + glyphosate benoxacor

B-265 metazachlor + H-1 benoxacor

B-266 metazachlor + glyphosate benoxacor

B-267 metazachlor + mesotrione benoxacor

B-268 metazachlor + nicosulfuron benoxacor

B-269 metazachlor + terbuthylazine benoxacor

B-270 metazachlor + topramezone benoxacor

B-271 metribuzin + glyphosate benoxacor

B-272 pendimethalin + H-1 benoxacor

B-273 pendimethalin + clodinafop-propargyl benoxacor

B-274 pendimethalin + fenoxaprop-P-ethyl benoxacor

B-275 pendimethalin + flupyrsulfuron-methyl-sodium benoxacor

B-276 pendimethalin + glyphosate benoxacor

B-277 pendimethalin + mesosulfuron-methyl benoxacor

B-278 pendimethalin + mesotrione benoxacor

B-279 pendimethalin + nicosulfuron benoxacor

B-280 pendimethalin + pinoxaden benoxacor

B-281 pendimethalin + pyroxsulam benoxacor

B-282 pendimethalin + tembotrione benoxacor

B-283 pendimethalin + topramezone benoxacor

B-284 pyroxasulfone + tembotrione benoxacor

B-285 pyroxasulfone + topramezone benoxacor

B-286 sulfentrazone + glyphosate benoxacor

B-287 terbuthylazine + H-1 benoxacor

B-288 terbuthylazine + foramsulfuron benoxacor

B-289 terbuthylazine + glyphosate benoxacor

B-290 terbuthylazine + mesotrione benoxacor

B-291 terbuthylazine + nicosulfuron benoxacor

B-292 terbuthylazine + tembotrione benoxacor

B-293 terbuthylazine + topramezone benoxacor

B-294 trifluralin + glyphosate benoxacor

B-295 clodinafop-propargyl cloquintocet

B-296 cycloxydim cloquintocet

B-297 cyhalofop-butyl cloquintocet

B-298 fenoxaprop-P-ethyl cloquintocet

B-299 pinoxaden cloquintocet Herbicide(s) B Safener C

B-300 profoxydim cloquintocet

B-301 tepraloxydim cloquintocet

B-302 tralkoxydim cloquintocet

B-303 esprocarb cloquintocet

B-304 prosulfocarb cloquintocet

B-305 thiobencarb cloquintocet

B-306 triallate cloquintocet

B-307 bensulfuron-methyl cloquintocet

B-308 bispyribac-sodium cloquintocet

B-309 cyclosulfamuron cloquintocet

B-310 flumetsulam cloquintocet

B-31 1 flupyrsulfuron-methyl-sodium cloquintocet

B-312 foramsulfuron cloquintocet

B-313 imazamox cloquintocet

B-314 imazapic cloquintocet

B-315 imazapyr cloquintocet

B-316 imazaquin cloquintocet

B-317 imazethapyr cloquintocet

B-318 imazosulfuron cloquintocet

B-319 iodosulfuron-methyl-sodium cloquintocet

B-320 mesosulfuron cloquintocet

B-321 nicosulfuron cloquintocet

B-322 penoxsulam cloquintocet

B-323 propoxycarbazone-sodium cloquintocet

B-324 pyrazosulfuron-ethyl cloquintocet

B-325 pyroxsulam cloquintocet

B-326 rimsulfuron cloquintocet

B-327 sulfosulfuron cloquintocet

B-328 thiencarbazone-methyl cloquintocet

B-329 tritosulfuron cloquintocet

B-330 2,4-D and its salts and esters cloquintocet

B-331 aminopyralid and its salts and esters cloquintocet

B-332 clopyralid and its salts and esters cloquintocet

B-333 dicamba and its salts and esters cloquintocet

B-334 fluroxypyr-meptyl cloquintocet

B-335 quinclorac cloquintocet

B-336 quinmerac cloquintocet

B-337 H-9 cloquintocet

B-338 diflufenzopyr cloquintocet Herbicide(s) B Safener C

B-339 diflufenzopyr-sodium cloquintocet

B-340 clomazone cloquintocet

B-341 diflufenican cloquintocet

B-342 fluorochloridone cloquintocet

B-343 isoxaflutol cloquintocet

B-344 mesotrione cloquintocet

B-345 picolinafen cloquintocet

B-346 sulcotrione cloquintocet

B-347 tefuryltrione cloquintocet

B-348 tembotrione cloquintocet

B-349 topramezone cloquintocet

B-350 H-7 cloquintocet

B-351 atrazine cloquintocet

B-352 diuron cloquintocet

B-353 fluometuron cloquintocet

B-354 hexazinone cloquintocet

B-355 isoproturon cloquintocet

B-356 metribuzin cloquintocet

B-357 propanil cloquintocet

B-358 terbuthylazine cloquintocet

B-359 paraquat dichloride cloquintocet

B-360 flumioxazin cloquintocet

B-361 oxyfluorfen cloquintocet

B-362 saflufenacil cloquintocet

B-363 sulfentrazone cloquintocet

B-364 H-1 cloquintocet

B-365 H-2 cloquintocet

B-366 glyphosate cloquintocet

B-367 glyphosate-isopropylammonium cloquintocet

B-368 glyphosate-trimesium (sulfosate) cloquintocet

B-369 glufosinate cloquintocet

B-370 glufosinate-ammonium cloquintocet

B-371 pendimethalin cloquintocet

B-372 trifluralin cloquintocet

B-373 acetochlor cloquintocet

B-374 cafenstrole cloquintocet

B-375 dimethenamid-P cloquintocet

B-376 fentrazamide cloquintocet

B-377 flufenacet cloquintocet Herbicide(s) B Safener C

B-378 mefenacet cloquintocet

B-379 metazachlor cloquintocet

B-380 metolachlor-S cloquintocet

B-381 pyroxasulfone cloquintocet

B-382 isoxaben cloquintocet

B-383 dymron cloquintocet

B-384 indanofan cloquintocet

B-385 oxaziclomefone cloquintocet

B-386 triaziflam cloquintocet

B-387 atrazine + H-1 cloquintocet

B-388 atrazine + glyphosate cloquintocet

B-389 atrazine + mesotrione cloquintocet

B-390 atrazine + nicosulfuron cloquintocet

B-391 atrazine + tembotrione cloquintocet

B-392 atrazine + topramezone cloquintocet

B-393 clomazone + glyphosate cloquintocet

B-394 diflufenican + clodinafop-propargyl cloquintocet

B-395 diflufenican + fenoxaprop-p-ethyl cloquintocet

B-396 diflufenican + flupyrsulfuron-methyl-sodium cloquintocet

B-397 diflufenican + glyphosate cloquintocet

B-398 diflufenican + mesosulfuron-methyl cloquintocet

B-399 diflufenican + pinoxaden cloquintocet

B-400 diflufenican + pyroxsulam cloquintocet

B-401 flumetsulam + glyphosate cloquintocet

B-402 flumioxazin + glyphosate cloquintocet

B-403 imazapic + glyphosate cloquintocet

B-404 imazethapyr + glyphosate cloquintocet

B-405 isoxaflutol + H-1 cloquintocet

B-406 isoxaflutol + glyphosate cloquintocet

B-407 metazachlor + H-1 cloquintocet

B-408 metazachlor + glyphosate cloquintocet

B-409 metazachlor + mesotrione cloquintocet

B-410 metazachlor + nicosulfuron cloquintocet

B-41 1 metazachlor + terbuthylazine cloquintocet

B-412 metazachlor + topramezone cloquintocet

B-413 metribuzin + glyphosate cloquintocet

B-414 pendimethalin + H-1 cloquintocet

B-415 pendimethalin + clodinafop-propargyl cloquintocet

B-416 pendimethalin + fenoxaprop-P-ethyl cloquintocet Herbicide(s) B Safener C

B-417 pendimethalin + flupyrsulfuron-methyl-sodium cloquintocet

B-418 pendimethalin + glyphosate cloquintocet

B-419 pendimethalin + mesosulfuron-methyl cloquintocet

B-420 pendimethalin + mesotrione cloquintocet

B-421 pendimethalin + nicosulfuron cloquintocet

B-422 pendimethalin + pinoxaden cloquintocet

B-423 pendimethalin + pyroxsulam cloquintocet

B-424 pendimethalin + tembotrione cloquintocet

B-425 pendimethalin + topramezone cloquintocet

B-426 pyroxasulfone + tembotrione cloquintocet

B-427 pyroxasulfone + topramezone cloquintocet

B-428 sulfentrazone + glyphosate cloquintocet

B-429 terbuthylazine + H-1 cloquintocet

B-430 terbuthylazine + foramsulfuron cloquintocet

B-431 terbuthylazine + glyphosate cloquintocet

B-432 terbuthylazine + mesotrione cloquintocet

B-433 terbuthylazine + nicosulfuron cloquintocet

B-434 terbuthylazine + tembotrione cloquintocet

B-435 terbuthylazine + topramezone cloquintocet

B-436 trifluralin + glyphosate cloquintocet

B-437 clodinafop-propargyl dichlormid

B-438 cycloxydim dichlormid

B-439 cyhalofop-butyl dichlormid

B-440 fenoxaprop-P-ethyl dichlormid

B-441 pinoxaden dichlormid

B-442 profoxydim dichlormid

B-443 tepraloxydim dichlormid

B-444 tralkoxydim dichlormid

B-445 esprocarb dichlormid

B-446 prosulfocarb dichlormid

B-447 thiobencarb dichlormid

B-448 triallate dichlormid

B-449 bensulfuron-methyl dichlormid

B-450 bispyribac-sodium dichlormid

B-451 cyclosulfamuron dichlormid

B-452 flumetsulam dichlormid

B-453 flupyrsulfuron-methyl-sodium dichlormid

B-454 foramsulfuron dichlormid

B-455 imazamox dichlormid Herbicide(s) B Safener C

B-456 imazapic dichlormid

B-457 imazapyr dichlormid

B-458 imazaquin dichlormid

B-459 imazethapyr dichlormid

B-460 imazosulfuron dichlormid

B-461 iodosulfuron-methyl-sodium dichlormid

B-462 mesosulfuron dichlormid

B-463 nicosulfuron dichlormid

B-464 penoxsulam dichlormid

B-465 propoxycarbazone-sodium dichlormid

B-466 pyrazosulfuron-ethyl dichlormid

B-467 pyroxsulam dichlormid

B-468 rimsulfuron dichlormid

B-469 sulfosulfuron dichlormid

B-470 thiencarbazone-methyl dichlormid

B-471 tritosulfuron dichlormid

B-472 2,4-D and its salts and esters dichlormid

B-473 aminopyralid and its salts and esters dichlormid

B-474 clopyralid and its salts and esters dichlormid

B-475 dicamba and its salts and esters dichlormid

B-476 fluroxypyr-meptyl dichlormid

B-477 quinclorac dichlormid

B-478 quinmerac dichlormid

B-479 H-9 dichlormid

B-480 diflufenzopyr dichlormid

B-481 diflufenzopyr-sodium dichlormid

B-482 clomazone dichlormid

B-483 diflufenican dichlormid

B-484 fluorochloridone dichlormid

B-485 isoxaflutol dichlormid

B-486 mesotrione dichlormid

B-487 picolinafen dichlormid

B-488 sulcotrione dichlormid

B-489 tefuryltrione dichlormid

B-490 tembotrione dichlormid

B-491 topramezone dichlormid

B-492 H-7 dichlormid

B-493 atrazine dichlormid

B-494 diuron dichlormid Herbicide(s) B Safener C

B-495 fluometuron dichlormid

B-496 hexazinone dichlormid

B-497 isoproturon dichlormid

B-498 metribuzin dichlormid

B-499 propanil dichlormid

B-500 terbuthylazine dichlormid

B-501 paraquat dichloride dichlormid

B-502 flumioxazin dichlormid

B-503 oxyfluorfen dichlormid

B-504 saflufenacil dichlormid

B-505 sulfentrazone dichlormid

B-506 H-1 dichlormid

B-507 H-2 dichlormid

B-508 glyphosate dichlormid

B-509 glyphosate-isopropylammonium dichlormid

B-510 glyphosate-trimesium (sulfosate) dichlormid

B-51 1 glufosinate dichlormid

B-512 glufosinate-ammonium dichlormid

B-513 pendimethalin dichlormid

B-514 trifluralin dichlormid

B-515 acetochlor dichlormid

B-516 cafenstrole dichlormid

B-517 dimethenamid-P dichlormid

B-518 fentrazamide dichlormid

B-519 flufenacet dichlormid

B-520 mefenacet dichlormid

B-521 metazachlor dichlormid

B-522 metolachlor-S dichlormid

B-523 pyroxasulfone dichlormid

B-524 isoxaben dichlormid

B-525 dymron dichlormid

B-526 indanofan dichlormid

B-527 oxaziclomefone dichlormid

B-528 triaziflam dichlormid

B-529 atrazine + H-1 dichlormid

B-530 atrazine + glyphosate dichlormid

B-531 atrazine + mesotrione dichlormid

B-532 atrazine + nicosulfuron dichlormid

B-533 atrazine + tembotrione dichlormid Herbicide(s) B Safener C

B-534 atrazine + topramezone dichlormid

B-535 clomazone + glyphosate dichlormid

B-536 diflufenican + clodinafop-propargyl dichlormid

B-537 diflufenican + fenoxaprop-p-ethyl dichlormid

B-538 diflufenican + flupyrsulfuron-methyl-sodium dichlormid

B-539 diflufenican + glyphosate dichlormid

B-540 diflufenican + mesosulfuron-methyl dichlormid

B-541 diflufenican + pinoxaden dichlormid

B-542 diflufenican + pyroxsulam dichlormid

B-543 flumetsulam + glyphosate dichlormid

B-544 flumioxazin + glyphosate dichlormid

B-545 imazapic + glyphosate dichlormid

B-546 imazethapyr + glyphosate dichlormid

B-547 isoxaflutol + H-1 dichlormid

B-548 isoxaflutol + glyphosate dichlormid

B-549 metazachlor + H-1 dichlormid

B-550 metazachlor + glyphosate dichlormid

B-551 metazachlor + mesotrione dichlormid

B-552 metazachlor + nicosulfuron dichlormid

B-553 metazachlor + terbuthylazine dichlormid

B-554 metazachlor + topramezone dichlormid

B-555 metribuzin + glyphosate dichlormid

B-556 pendimethalin + H-1 dichlormid

B-557 pendimethalin + clodinafop-propargyl dichlormid

B-558 pendimethalin + fenoxaprop-P-ethyl dichlormid

B-559 pendimethalin + flupyrsulfuron-methyl-sodium dichlormid

B-560 pendimethalin + glyphosate dichlormid

B-561 pendimethalin + mesosulfuron-methyl dichlormid

B-562 pendimethalin + mesotrione dichlormid

B-563 pendimethalin + nicosulfuron dichlormid

B-564 pendimethalin + pinoxaden dichlormid

B-565 pendimethalin + pyroxsulam dichlormid

B-566 pendimethalin + tembotrione dichlormid

B-567 pendimethalin + topramezone dichlormid

B-568 pyroxasulfone + tembotrione dichlormid

B-569 pyroxasulfone + topramezone dichlormid

B-570 sulfentrazone + glyphosate dichlormid

B-571 terbuthylazine + H-1 dichlormid

B-572 terbuthylazine + foramsulfuron dichlormid Herbicide(s) B Safener C

B-573 terbuthylazine + glyphosate dichlormid

B-574 terbuthylazine + mesotrione dichlormid

B-575 terbuthylazine + nicosulfuron dichlormid

B-576 terbuthylazine + tembotrione dichlormid

B-577 terbuthylazine + topramezone dichlormid

B-578 trifluralin + glyphosate dichlormid

B-579 clodinafop-propargyl fenchlorazole

B-580 cycloxydim fenchlorazole

B-581 cyhalofop-butyl fenchlorazole

B-582 fenoxaprop-P-ethyl fenchlorazole

B-583 pinoxaden fenchlorazole

B-584 profoxydim fenchlorazole

B-585 tepraloxydim fenchlorazole

B-586 tralkoxydim fenchlorazole

B-587 esprocarb fenchlorazole

B-588 prosulfocarb fenchlorazole

B-589 thiobencarb fenchlorazole

B-590 triallate fenchlorazole

B-591 bensulfuron-methyl fenchlorazole

B-592 bispyribac-sodium fenchlorazole

B-593 cyclosulfamuron fenchlorazole

B-594 flumetsulam fenchlorazole

B-595 flupyrsulfuron-methyl-sodium fenchlorazole

B-596 foramsulfuron fenchlorazole

B-597 imazamox fenchlorazole

B-598 imazapic fenchlorazole

B-599 imazapyr fenchlorazole

B-600 imazaquin fenchlorazole

B-601 imazethapyr fenchlorazole

B-602 imazosulfuron fenchlorazole

B-603 iodosulfuron-methyl-sodium fenchlorazole

B-604 mesosulfuron fenchlorazole

B-605 nicosulfuron fenchlorazole

B-606 penoxsulam fenchlorazole

B-607 propoxycarbazone-sodium fenchlorazole

B-608 pyrazosulfuron-ethyl fenchlorazole

B-609 pyroxsulam fenchlorazole

B-610 rimsulfuron fenchlorazole

B-61 1 sulfosulfuron fenchlorazole Herbicide(s) B Safener C

B-612 thiencarbazone-methyl fenchlorazole

B-613 tritosulfuron fenchlorazole

B-614 2,4-D and its salts and esters fenchlorazole

B-615 aminopyralid and its salts and esters fenchlorazole

B-616 clopyralid and its salts and esters fenchlorazole

B-617 dicamba and its salts and esters fenchlorazole

B-618 fluroxypyr-meptyl fenchlorazole

B-619 quinclorac fenchlorazole

B-620 quinmerac fenchlorazole

B-621 H-9 fenchlorazole

B-622 diflufenzopyr fenchlorazole

B-623 diflufenzopyr-sodium fenchlorazole

B-624 clomazone fenchlorazole

B-625 diflufenican fenchlorazole

B-626 fluorochloridone fenchlorazole

B-627 isoxaflutol fenchlorazole

B-628 mesotrione fenchlorazole

B-629 picolinafen fenchlorazole

B-630 sulcotrione fenchlorazole

B-631 tefuryltrione fenchlorazole

B-632 tembotrione fenchlorazole

B-633 topramezone fenchlorazole

B-634 H-7 fenchlorazole

B-635 atrazine fenchlorazole

B-636 diuron fenchlorazole

B-637 fluometuron fenchlorazole

B-638 hexazinone fenchlorazole

B-639 isoproturon fenchlorazole

B-640 metribuzin fenchlorazole

B-641 propanil fenchlorazole

B-642 terbuthylazine fenchlorazole

B-643 paraquat dichloride fenchlorazole

B-644 flumioxazin fenchlorazole

B-645 oxyfluorfen fenchlorazole

B-646 saflufenacil fenchlorazole

B-647 sulfentrazone fenchlorazole

B-648 H-1 fenchlorazole

B-649 H-2 fenchlorazole

B-650 glyphosate fenchlorazole Herbicide(s) B Safener C

B-651 glyphosate-isopropylammonium fenchlorazole

B-652 glyphosate-trimesium (sulfosate) fenchlorazole

B-653 glufosinate fenchlorazole

B-654 glufosinate-ammonium fenchlorazole

B-655 pendimethalin fenchlorazole

B-656 trifluralin fenchlorazole

B-657 acetochlor fenchlorazole

B-658 cafenstrole fenchlorazole

B-659 dimethenamid-P fenchlorazole

B-660 fentrazamide fenchlorazole

B-661 flufenacet fenchlorazole

B-662 mefenacet fenchlorazole

B-663 metazachlor fenchlorazole

B-664 metolachlor-S fenchlorazole

B-665 pyroxasulfone fenchlorazole

B-666 isoxaben fenchlorazole

B-667 dymron fenchlorazole

B-668 indanofan fenchlorazole

B-669 oxaziclomefone fenchlorazole

B-670 triaziflam fenchlorazole

B-671 atrazine + H-1 fenchlorazole

B-672 atrazine + glyphosate fenchlorazole

B-673 atrazine + mesotrione fenchlorazole

B-674 atrazine + nicosulfuron fenchlorazole

B-675 atrazine + tembotrione fenchlorazole

B-676 atrazine + topramezone fenchlorazole

B-677 clomazone + glyphosate fenchlorazole

B-678 diflufenican + clodinafop-propargyl fenchlorazole

B-679 diflufenican + fenoxaprop-P-ethyl fenchlorazole

B-680 diflufenican + flupyrsulfuron-methyl-sodium fenchlorazole

B-681 diflufenican + glyphosate fenchlorazole

B-682 diflufenican + mesosulfuron-methyl fenchlorazole

B-683 diflufenican + pinoxaden fenchlorazole

B-684 diflufenican + pyroxsulam fenchlorazole

B-685 flumetsulam + glyphosate fenchlorazole

B-686 flumioxazin + glyphosate fenchlorazole

B-687 imazapic + glyphosate fenchlorazole

B-688 imazethapyr + glyphosate fenchlorazole

B-689 isoxaflutol + H-1 fenchlorazole Herbicide(s) B Safener C

B-690 isoxaflutol + glyphosate fenchlorazole

B-691 metazachlor + H-1 fenchlorazole

B-692 metazachlor + glyphosate fenchlorazole

B-693 metazachlor + mesotrione fenchlorazole

B-694 metazachlor + nicosulfuron fenchlorazole

B-695 metazachlor + terbuthylazine fenchlorazole

B-696 metazachlor + topramezone fenchlorazole

B-697 metribuzin + glyphosate fenchlorazole

B-698 pendimethalin + H-1 fenchlorazole

B-699 pendimethalin + clodinafop-propargyl fenchlorazole

B-700 pendimethalin + fenoxaprop-P-ethyl fenchlorazole

B-701 pendimethalin + flupyrsulfuron-methyl-sodium fenchlorazole

B-702 pendimethalin + glyphosate fenchlorazole

B-703 pendimethalin + mesosulfuron-methyl fenchlorazole

B-704 pendimethalin + mesotrione fenchlorazole

B-705 pendimethalin + nicosulfuron fenchlorazole

B-706 pendimethalin + pinoxaden fenchlorazole

B-707 pendimethalin + pyroxsulam fenchlorazole

B-708 pendimethalin + tembotrione fenchlorazole

B-709 pendimethalin + topramezone fenchlorazole

B-710 pyroxasulfone + tembotrione fenchlorazole

B-71 1 pyroxasulfone + topramezone fenchlorazole

B-712 sulfentrazone + glyphosate fenchlorazole

B-713 terbuthylazine + H-1 fenchlorazole

B-714 terbuthylazine + foramsulfuron fenchlorazole

B-715 terbuthylazine + glyphosate fenchlorazole

B-716 terbuthylazine + mesotrione fenchlorazole

B-717 terbuthylazine + nicosulfuron fenchlorazole

B-718 terbuthylazine + tembotrione fenchlorazole

B-719 terbuthylazine + topramezone fenchlorazole

B-720 trifluralin + glyphosate fenchlorazole

B-721 clodinafop-propargyl isoxadifen

B-722 cycloxydim isoxadifen

B-723 cyhalofop-butyl isoxadifen

B-724 fenoxaprop-P-ethyl isoxadifen

B-725 pinoxaden isoxadifen

B-726 profoxydim isoxadifen

B-727 tepraloxydim isoxadifen

B-728 tralkoxydim isoxadifen Herbicide(s) B Safener C

B-729 esprocarb isoxadifen

B-730 prosulfocarb isoxadifen

B-731 thiobencarb isoxadifen

B-732 triallate isoxadifen

B-733 bensulfuron-methyl isoxadifen

B-734 bispyribac-sodium isoxadifen

B-735 cyclosulfamuron isoxadifen

B-736 flumetsulam isoxadifen

B-737 flupyrsulfuron-methyl-sodium isoxadifen

B-738 foramsulfuron isoxadifen

B-739 imazamox isoxadifen

B-740 imazapic isoxadifen

B-741 imazapyr isoxadifen

B-742 imazaquin isoxadifen

B-743 imazethapyr isoxadifen

B-744 imazosulfuron isoxadifen

B-745 iodosulfuron-methyl-sodium isoxadifen

B-746 mesosulfuron isoxadifen

B-747 nicosulfuron isoxadifen

B-748 penoxsulam isoxadifen

B-749 propoxycarbazone-sodium isoxadifen

B-750 pyrazosulfuron-ethyl isoxadifen

B-751 pyroxsulam isoxadifen

B-752 rimsulfuron isoxadifen

B-753 sulfosulfuron isoxadifen

B-754 thiencarbazone-methyl isoxadifen

B-755 tritosulfuron isoxadifen

B-756 2,4-D and its salts and esters isoxadifen

B-757 aminopyralid and its salts and esters isoxadifen

B-758 clopyralid and its salts and esters isoxadifen

B-759 dicamba and its salts and esters isoxadifen

B-760 fluroxypyr-meptyl isoxadifen

B-761 quinclorac isoxadifen

B-762 quinmerac isoxadifen

B-763 H-9 isoxadifen

B-764 diflufenzopyr isoxadifen

B-765 diflufenzopyr-sodium isoxadifen

B-766 clomazone isoxadifen

B-767 diflufenican isoxadifen Herbicide(s) B Safener C

B-768 fluorochloridone isoxadifen

B-769 isoxaflutol isoxadifen

B-770 mesotrione isoxadifen

B-771 picolinafen isoxadifen

B-772 sulcotrione isoxadifen

B-773 tefuryltrione isoxadifen

B-774 tembotrione isoxadifen

B-775 topramezone isoxadifen

B-776 H-7 isoxadifen

B-777 atrazine isoxadifen

B-778 diuron isoxadifen

B-779 fluometuron isoxadifen

B-780 hexazinone isoxadifen

B-781 isoproturon isoxadifen

B-782 metribuzin isoxadifen

B-783 propanil isoxadifen

B-784 terbuthylazine isoxadifen

B-785 paraquat dichloride isoxadifen

B-786 flumioxazin isoxadifen

B-787 oxyfluorfen isoxadifen

B-788 saflufenacil isoxadifen

B-789 sulfentrazone isoxadifen

B-790 H-1 isoxadifen

B-791 H-2 isoxadifen

B-792 glyphosate isoxadifen

B-793 glyphosate-isopropylammonium isoxadifen

B-794 glyphosate-trimesium (sulfosate) isoxadifen

B-795 glufosinate isoxadifen

B-796 glufosinate-ammonium isoxadifen

B-797 pendimethalin isoxadifen

B-798 trifluralin isoxadifen

B-799 acetochlor isoxadifen

B-800 cafenstrole isoxadifen

B-801 dimethenamid-P isoxadifen

B-802 fentrazamide isoxadifen

B-803 flufenacet isoxadifen

B-804 mefenacet isoxadifen

B-805 metazachlor isoxadifen

B-806 metolachlor-S isoxadifen Herbicide(s) B Safener C

B-807 pyroxasulfone isoxadifen

B-808 isoxaben isoxadifen

B-809 dymron isoxadifen

B-810 indanofan isoxadifen

B-81 1 oxaziclomefone isoxadifen

B-812 triaziflam isoxadifen

B-813 atrazine + H-1 isoxadifen

B-814 atrazine + glyphosate isoxadifen

B-815 atrazine + mesotrione isoxadifen

B-816 atrazine + nicosulfuron isoxadifen

B-817 atrazine + tembotrione isoxadifen

B-818 atrazine + topramezone isoxadifen

B-819 clomazone + glyphosate isoxadifen

B-820 diflufenican + clodinafop-propargyl isoxadifen

B-821 diflufenican + fenoxaprop-P-ethyl isoxadifen

B-822 diflufenican + flupyrsulfuron-methyl-sodium isoxadifen

B-823 diflufenican + glyphosate isoxadifen

B-824 diflufenican + mesosulfuron-methyl isoxadifen

B-825 diflufenican + pinoxaden isoxadifen

B-826 diflufenican + pyroxsulam isoxadifen

B-827 flumetsulam + glyphosate isoxadifen

B-828 flumioxazin + glyphosate isoxadifen

B-829 imazapic + glyphosate isoxadifen

B-830 imazethapyr + glyphosate isoxadifen

B-831 isoxaflutol + H-1 isoxadifen

B-832 isoxaflutol + glyphosate isoxadifen

B-833 metazachlor + H-1 isoxadifen

B-834 metazachlor + glyphosate isoxadifen

B-835 metazachlor + mesotrione isoxadifen

B-836 metazachlor + nicosulfuron isoxadifen

B-837 metazachlor + terbuthylazine isoxadifen

B-838 metazachlor + topramezone isoxadifen

B-839 metribuzin + glyphosate isoxadifen

B-840 pendimethalin + H-1 isoxadifen

B-841 pendimethalin + clodinafop-propargyl isoxadifen

B-842 pendimethalin + fenoxaprop-P-ethyl isoxadifen

B-843 pendimethalin + flupyrsulfuron-methyl-sodium isoxadifen

B-844 pendimethalin + glyphosate isoxadifen

B-845 pendimethalin + mesosulfuron-methyl isoxadifen Herbicide(s) B Safener C

B-846 pendimethalin + mesotrione isoxadifen

B-847 pendimethalin + nicosulfuron isoxadifen

B-848 pendimethalin + pinoxaden isoxadifen

B-849 pendimethalin + pyroxsulam isoxadifen

B-850 pendimethalin + tembotrione isoxadifen

B-851 pendimethalin + topramezone isoxadifen

B-852 pyroxasulfone + tembotrione isoxadifen

B-853 pyroxasulfone + topramezone isoxadifen

B-854 sulfentrazone + glyphosate isoxadifen

B-855 terbuthylazine + H-1 isoxadifen

B-856 terbuthylazine + foramsulfuron isoxadifen

B-857 terbuthylazine + glyphosate isoxadifen

B-858 terbuthylazine + mesotrione isoxadifen

B-859 terbuthylazine + nicosulfuron isoxadifen

B-860 terbuthylazine + tembotrione isoxadifen

B-861 terbuthylazine + topramezone isoxadifen

B-862 trifluralin + glyphosate isoxadifen

B-863 clodinafop-propargyl mefenpyr

B-864 cycloxydim mefenpyr

B-865 cyhalofop-butyl mefenpyr

B-866 fenoxaprop-P-ethyl mefenpyr

B-867 pinoxaden mefenpyr

B-868 profoxydim mefenpyr

B-869 tepraloxydim mefenpyr

B-870 tralkoxydim mefenpyr

B-871 esprocarb mefenpyr

B-872 prosulfocarb mefenpyr

B-873 thiobencarb mefenpyr

B-874 triallate mefenpyr

B-875 bensulfuron-methyl mefenpyr

B-876 bispyribac-sodium mefenpyr

B-877 cyclosulfamuron mefenpyr

B-878 flumetsulam mefenpyr

B-879 flupyrsulfuron-methyl-sodium mefenpyr

B-880 foramsulfuron mefenpyr

B-881 imazamox mefenpyr

B-882 imazapic mefenpyr

B-883 imazapyr mefenpyr

B-884 imazaquin mefenpyr Herbicide(s) B Safener C

B-885 imazethapyr mefenpyr

B-886 imazosulfuron mefenpyr

B-887 iodosulfuron-methyl-sodium mefenpyr

B-888 mesosulfuron mefenpyr

B-889 nicosulfuron mefenpyr

B-890 penoxsulam mefenpyr

B-891 propoxycarbazone-sodium mefenpyr

B-892 pyrazosulfuron-ethyl mefenpyr

B-893 pyroxsulam mefenpyr

B-894 rimsulfuron mefenpyr

B-895 sulfosulfuron mefenpyr

B-896 thiencarbazone-methyl mefenpyr

B-897 tritosulfuron mefenpyr

B-898 2,4-D and its salts and esters mefenpyr

B-899 aminopyralid and its salts and esters mefenpyr

B-900 clopyralid and its salts and esters mefenpyr

B-901 dicamba and its salts and esters mefenpyr

B-902 fluroxypyr-meptyl mefenpyr

B-903 quinclorac mefenpyr

B-904 quinmerac mefenpyr

B-905 H-9 mefenpyr

B-906 diflufenzopyr mefenpyr

B-907 diflufenzopyr-sodium mefenpyr

B-908 clomazone mefenpyr

B-909 diflufenican mefenpyr

B-910 fluorochloridone mefenpyr

B-91 1 isoxaflutol mefenpyr

B-912 mesotrione mefenpyr

B-913 picolinafen mefenpyr

B-914 sulcotrione mefenpyr

B-915 tefuryltrione mefenpyr

B-916 tembotrione mefenpyr

B-917 topramezone mefenpyr

B-918 H-7 mefenpyr

B-919 atrazine mefenpyr

B-920 diuron mefenpyr

B-921 fluometuron mefenpyr

B-922 hexazinone mefenpyr

B-923 isoproturon mefenpyr Herbicide(s) B Safener C

B-924 metribuzin mefenpyr

B-925 propanil mefenpyr

B-926 terbuthylazine mefenpyr

B-927 paraquat dichloride mefenpyr

B-928 flumioxazin mefenpyr

B-929 oxyfluorfen mefenpyr

B-930 saflufenacil mefenpyr

B-931 sulfentrazone mefenpyr

B-932 H-1 mefenpyr

B-933 H-2 mefenpyr

B-934 glyphosate mefenpyr

B-935 glyphosate-isopropylammonium mefenpyr

B-936 glyphosate-trimesium (sulfosate) mefenpyr

B-937 glufosinate mefenpyr

B-938 glufosinate-ammonium mefenpyr

B-939 pendimethalin mefenpyr

B-940 trifluralin mefenpyr

B-941 acetochlor mefenpyr

B-942 cafenstrole mefenpyr

B-943 dimethenamid-P mefenpyr

B-944 fentrazamide mefenpyr

B-945 flufenacet mefenpyr

B-946 mefenacet mefenpyr

B-947 metazachlor mefenpyr

B-948 metolachlor-S mefenpyr

B-949 pyroxasulfone mefenpyr

B-950 isoxaben mefenpyr

B-951 dymron mefenpyr

B-952 indanofan mefenpyr

B-953 oxaziclomefone mefenpyr

B-954 triaziflam mefenpyr

B-955 atrazine + H-1 mefenpyr

B-956 atrazine + glyphosate mefenpyr

B-957 atrazine + mesotrione mefenpyr

B-958 atrazine + nicosulfuron mefenpyr

B-959 atrazine + tembotrione mefenpyr

B-960 atrazine + topramezone mefenpyr

B-961 clomazone + glyphosate mefenpyr

B-962 diflufenican + clodinafop-propargyl mefenpyr Herbicide(s) B Safener C

B-963 diflufenican + fenoxaprop-P-ethyl mefenpyr

B-964 diflufenican + flupyrsulfuron-methyl-sodium mefenpyr

B-965 diflufenican + glyphosate mefenpyr

B-966 diflufenican + mesosulfuron-methyl mefenpyr

B-967 diflufenican + pinoxaden mefenpyr

B-968 diflufenican + pyroxsulam mefenpyr

B-969 flumetsulam + glyphosate mefenpyr

B-970 flumioxazin + glyphosate mefenpyr

B-971 imazapic + glyphosate mefenpyr

B-972 imazethapyr + glyphosate mefenpyr

B-973 isoxaflutol + H-1 mefenpyr

B-974 isoxaflutol + glyphosate mefenpyr

B-975 metazachlor + H-1 mefenpyr

B-976 metazachlor + glyphosate mefenpyr

B-977 metazachlor + mesotrione mefenpyr

B-978 metazachlor + nicosulfuron mefenpyr

B-979 metazachlor + terbuthylazine mefenpyr

B-980 metazachlor + topramezone mefenpyr

B-981 metribuzin + glyphosate mefenpyr

B-982 pendimethalin + H-1 mefenpyr

B-983 pendimethalin + clodinafop-propargyl mefenpyr

B-984 pendimethalin + fenoxaprop-P-ethyl mefenpyr

B-985 pendimethalin + flupyrsulfuron-methyl-sodium mefenpyr

B-986 pendimethalin + glyphosate mefenpyr

B-987 pendimethalin + mesosulfuron-methyl mefenpyr

B-988 pendimethalin + mesotrione mefenpyr

B-989 pendimethalin + nicosulfuron mefenpyr

B-990 pendimethalin + pinoxaden mefenpyr

B-991 pendimethalin + pyroxsulam mefenpyr

B-992 pendimethalin + tembotrione mefenpyr

B-993 pendimethalin + topramezone mefenpyr

B-994 pyroxasulfone + tembotrione mefenpyr

B-995 pyroxasulfone + topramezone mefenpyr

B-996 sulfentrazone + glyphosate mefenpyr

B-997 terbuthylazine + H-1 mefenpyr

B-998 terbuthylazine + foramsulfuron mefenpyr

B-999 terbuthylazine + glyphosate mefenpyr

B-1000 terbuthylazine + mesotrione mefenpyr

B-1001 terbuthylazine + nicosulfuron mefenpyr Herbicide(s) B Safener C

B-1002 terbuthylazine + tembotrione mefenpyr

B-1003 terbuthylazine + topramezone mefenpyr

B-1004 trifluralin + glyphosate mefenpyr

B-1005 clodinafop-propargyl H-12

B-1006 cycloxydim H-12

B-1007 cyhalofop-butyl H-12

B-1008 fenoxaprop-P-ethyl H-12

B-1009 pinoxaden H-12

B-1010 profoxydim H-12

B-101 1 tepraloxydim H-12

B-1012 tralkoxydim H-12

B-1013 esprocarb H-12

B-1014 prosulfocarb H-12

B-1015 thiobencarb H-12

B-1016 triallate H-12

B-1017 bensulfuron-methyl H-12

B-1018 bispyribac-sodium H-12

B-1019 cyclosulfamuron H-12

B-1020 flumetsulam H-12

B-1021 flupyrsulfuron-methyl-sodium H-12

B-1022 foramsulfuron H-12

B-1023 imazamox H-12

B-1024 imazapic H-12

B-1025 imazapyr H-12

B-1026 imazaquin H-12

B-1027 imazethapyr H-12

B-1028 imazosulfuron H-12

B-1029 iodosulfuron-methyl-sodium H-12

B-1030 mesosulfuron H-12

B-1031 nicosulfuron H-12

B-1032 penoxsulam H-12

B-1033 propoxycarbazone-sodium H-12

B-1034 pyrazosulfuron-ethyl H-12

B-1035 pyroxsulam H-12

B-1036 rimsulfuron H-12

B-1037 sulfosulfuron H-12

B-1038 thiencarbazone-methyl H-12

B-1039 tritosulfuron H-12

B-1040 2,4-D and its salts and esters H-12 Herbicide(s) B Safener C

B-1041 aminopyralid and its salts and esters H-12

B-1042 clopyralid and its salts and esters H-12

B-1043 dicamba and its salts and esters H-12

B-1044 fluroxypyr-meptyl H-12

B-1045 quinclorac H-12

B-1046 quinmerac H-12

B-1047 H-9 H-12

B-1048 diflufenzopyr H-12

B-1049 diflufenzopyr-sodium H-12

B-1050 clomazone H-12

B-1051 diflufenican H-12

B-1052 fluorochloridone H-12

B-1053 isoxaflutol H-12

B-1054 mesotrione H-12

B-1055 picolinafen H-12

B-1056 sulcotrione H-12

B-1057 tefuryltrione H-12

B-1058 tembotrione H-12

B-1059 topramezone H-12

B-1060 H-7 H-12

B-1061 atrazine H-12

B-1062 diuron H-12

B-1063 fluometuron H-12

B-1064 hexazinone H-12

B-1065 isoproturon H-12

B-1066 metribuzin H-12

B-1067 propanil H-12

B-1068 terbuthylazine H-12

B-1069 paraquat dichloride H-12

B-1070 flumioxazin H-12

B-1071 oxyfluorfen H-12

B-1072 saflufenacil H-12

B-1073 sulfentrazone H-12

B-1074 H-1 H-12

B-1075 H-2 H-12

B-1076 glyphosate H-12

B-1077 glyphosate-isopropylammonium H-12

B-1078 glyphosate-trimesium (sulfosate) H-12

B-1079 glufosinate H-12 Herbicide(s) B Safener C

B-1080 glufosinate-ammonium H-12

B-1081 pendimethalin H-12

B-1082 trifluralin H-12

B-1083 acetochlor H-12

B-1084 cafenstrole H-12

B-1085 dimethenamid-P H-12

B-1086 fentrazamide H-12

B-1087 flufenacet H-12

B-1088 mefenacet H-12

B-1089 metazachlor H-12

B-1090 metolachlor-S H-12

B-1091 pyroxasulfone H-12

B-1092 isoxaben H-12

B-1093 dymron H-12

B-1094 indanofan H-12

B-1095 oxaziclomefone H-12

B-1096 triaziflam H-12

B-1097 atrazine + H-1 H-12

B-1098 atrazine + glyphosate H-12

B-1099 atrazine + mesotrione H-12

B-1100 atrazine + nicosulfuron H-12

B-1101 atrazine + tembotrione H-12

B-1102 atrazine + topramezone H-12

B-1103 clomazone + glyphosate H-12

B-1104 diflufenican + clodinafop-propargyl H-12

B-1105 diflufenican + fenoxaprop-P-ethyl H-12

B-1106 diflufenican + flupyrsulfuron-methyl-sodium H-12

B-1107 diflufenican + glyphosate H-12

B-1108 diflufenican + mesosulfuron-methyl H-12

B-1109 diflufenican + pinoxaden H-12

B-1110 diflufenican + pyroxsulam H-12

B-1111 flumetsulam + glyphosate H-12

B-1112 flumioxazin + glyphosate H-12

B-1113 imazapic + glyphosate H-12

B-1114 imazethapyr + glyphosate H-12

B-1115 isoxaflutol + H-1 H-12

B-1116 isoxaflutol + glyphosate H-12

B-1117 metazachlor + H-1 H-12

B-1118 metazachlor + glyphosate H-12 Herbicide(s) B Safener C

B-1119 metazachlor + mesotrione H-12

B-1120 metazachlor + nicosulfuron H-12

B-1121 metazachlor + terbuthylazine H-12

B-1122 metazachlor + topramezone H-12

B-1123 metribuzin + glyphosate H-12

B-1124 pendimethalin + H-1 H-12

B-1125 pendimethalin + clodinafop-propargyl H-12

B-1126 pendimethalin + fenoxaprop-P-ethyl H-12

B-1127 pendimethalin + flupyrsulfuron-methyl-sodium H-12

B-1128 pendimethalin + glyphosate H-12

B-1129 pendimethalin + mesosulfuron-methyl H-12

B-1130 pendimethalin + mesotrione H-12

B-1131 pendimethalin + nicosulfuron H-12

B-1132 pendimethalin + pinoxaden H-12

B-1133 pendimethalin + pyroxsulam H-12

B-1134 pendimethalin + tembotrione H-12

B-1135 pendimethalin + topramezone H-12

B-1136 pyroxasulfone + tembotrione H-12

B-1137 pyroxasulfone + topramezone H-12

B-1138 sulfentrazone + glyphosate H-12

B-1139 terbuthylazine + H-1 H-12

B-1140 terbuthylazine + foramsulfuron H-12

B-1141 terbuthylazine + glyphosate H-12

B-1142 terbuthylazine + mesotrione H-12

B-1143 terbuthylazine + nicosulfuron H-12

B-1144 terbuthylazine + tembotrione H-12

B-1145 terbuthylazine + topramezone H-12

B-1146 trifluralin + glyphosate H-12

B-1147 2-1 —

B-1148 2-2 —

B-1149 2-3 —

B-1150 2-4 —

B-1151 2-5 —

B-1152 2-6 —

B-1153 2-7 —

B-1154 2-8 —

B-1155 2-9 —

B-1156 2-1 benoxacor

B-1157 2-2 benoxacor Herbicide(s) B Safener C

B-1158 2-3 benoxacor

B-1159 2-4 benoxacor

B-1160 2-5 benoxacor

B-1161 2-6 benoxacor

B-1162 2-7 benoxacor

B-1163 2-8 benoxacor

B-1164 2-9 benoxacor

B-1165 2-1 cloquintocet

B-1166 2-2 cloquintocet

B-1167 2-3 cloquintocet

B-1168 2-4 cloquintocet

B-1169 2-5 cloquintocet

B-1170 2-6 cloquintocet

B-1171 2-7 cloquintocet

B-1172 2-8 cloquintocet

B-1173 2-9 cloquintocet

B-1174 2-1 cyprosulfamide

B-1175 2-2 cyprosulfamide

B-1176 2-3 cyprosulfamide

B-1177 2-4 cyprosulfamide

B-1178 2-5 cyprosulfamide

B-1179 2-6 cyprosulfamide

B-1180 2-7 cyprosulfamide

B-1181 2-8 cyprosulfamide

B-1182 2-9 cyprosulfamide

B-1183 2-1 dichlormid

B-1184 2-2 dichlormid

B-1185 2-3 dichlormid

B-1186 2-4 dichlormid

B-1187 2-5 dichlormid

B-1188 2-6 dichlormid

B-1189 2-7 dichlormid

B-1190 2-8 dichlormid

B-1191 2-9 dichlormid

B-1192 2-1 fenchlorazole

B-1193 2-2 fenchlorazole

B-1194 2-3 fenchlorazole

B-1195 2-4 fenchlorazole

B-1196 2-5 fenchlorazole Herbicide(s) B Safener C

B-1 197 2-6 fenchlorazole

B-1 198 2-7 fenchlorazole

B-1 199 2-8 fenchlorazole

B-1200 2-9 fenchlorazole

B-1201 2-1 isoxadifen

B-1202 2-2 isoxadifen

B-1203 2-3 isoxadifen

B-1204 2-4 isoxadifen

B-1205 2-5 isoxadifen

B-1206 2-6 isoxadifen

B-1207 2-7 isoxadifen

B-1208 2-8 isoxadifen

B-1209 2-9 isoxadifen

B-1210 2-1 mefenpyr

B-121 1 2-2 mefenpyr

B-1212 2-3 mefenpyr

B-1213 2-4 mefenpyr

B-1214 2-5 mefenpyr

B-1215 2-6 mefenpyr

B-1216 2-7 mefenpyr

B-1217 2-8 mefenpyr

B-1218 2-9 mefenpyr

B-1219 2-1 H-1 1

B-1220 2-2 H-1 1

B-1221 2-3 H-1 1

B-1222 2-4 H-1 1

B-1223 2-5 H-1 1

B-1224 2-6 H-1 1

B-1225 2-7 H-1 1

B-1226 2-8 H-1 1

B-1227 2-9 H-1 1

B-1228 2-1 H-12

B-1229 2-2 H-12

B-1230 2-3 H-12

B-1231 2-4 H-12

B-1232 2-5 H-12

B-1233 2-6 H-12

B-1234 2-7 H-12

B-1235 2-8 H-12 Herbicide(s) B Safener C

B-1236 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 a way 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 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.

I. Synthesis examples

With appropriate modification of the starting materials, the procedures given in the syn- thesis examples below were used to obtain further compounds I. The compounds obtained in this manner are listed in the Tables C and D that follow, 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; HPLC column: 15 RP-18 column (Chromolith Speed ROD from Merck KgaA, Germany), 50^*4.6 mm; mobile phase: acetonitrile + 0.1 % trifluoroacetic acid (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). Example 1 : Preparation of 2,4-dichloro-3-[2-(dimethylamino)-1 ,1 -dimethyl-2-oxo-ethoxy]-

6-fluoro-N-(1 -methyltetrazol-5-yl)benzamide (Compound I.A.V.37 of Table 4)

Step 1 : 2-(2,6-dichloro-4-fluoro-phenoxy)-2-methyl-propanoic acid

Commercially available 2,6-dichloro-4-fluoro-phenol (CAS 392-71 -2, 8.0 g, 0.044 mol) was dissolved acetone (40 mL). Powdered sodium hydroxide (1 1.6 g, 0.292 mol) was added to the solution. The mixture was warmed to reflux. External heating was removed and chloroform (7.91 g, 0.066 mol) was added so rapid that the mixture kept boiling. Afterwards the mixture was re- fluxed for 4 h. After removal of volatiles water was added to the residue. The solution was adjusted to pH 7 with 2 N hydrochloric acid and extracted with 50 mL methylene chloride. The aqueous layer was adjusted to pH 4 and again extracted with 50 mL methylene chloride. The solvent of the acidic extract was evaporated and the crude product purified by column chromatography to yield 3.97 g of a pale white solid.

H NMR (400 MHz, CDCI₃), δ 1 ,62 (s, 6 H), 7,10 (d, 2 H), 1 1 -12 (br s, 1 H).

Step 2: 2-(2,6-dichloro-4-fluoro-phenoxy)-N,N,2-trimethyl-propanamide

2-(2,6-dichloro-4-fluoro-phenoxy)-2-methyl-propanoic acid (0.975 g, 0.004 mol) was dissolved in 5 mL methylene chloride. 1 drop of DMF was added. Then oxalyl chloride (0.695 g, 0.005 mol) was added at 0°C. After stirring overnight at 25°C the volatiles were evaporated. The residue was suspended in 5 mL THF. Then a 2 molar solution of dimethylamine (5.5 mL) in THF was added under warming to 40°C. After stirring for 1.5 h the volatiles were evaporated and the residue partitioned between water and methylene chloride. The water phase was made acidic with 0.5 molar hydrochloric acid. The organic phase was dried with Na2S0₄. The crude product obtained after evaporation of the solvent was purified by column chromatography to yield 0.67 g of a pale white solid.

LC-MS (M+H): 294.

H NMR (400 MHz, CDC ), δ 1 ,57 (s, 6 H), 3,0 (s, 3 H), 3,37 (s, 3H), 7,06 (d, 2 H).

Step 3: 2,4-dichloro-3-[2-(dimethylamino)-1 ,1 -dimethyl-2-oxo-ethoxy]-6-fluoro-benzoic acid

2-(2,6-dichloro-4-fluoro-phenoxy)-N,N,2-trimethyl-propanamide (0.6 g, 0.002 mol) were dissolved in 10 mL THF and then 1.07 ml. of a 2 molar solution of lithium diisopropylamide in THF were added at -75°C. After 1 h at -75°C crushed dry ice was added to the solution. After stirring overnight at 25°C the reaction mixture was quenched with 0.5 molar hydrochloric acid. The organic phase was separated and the aqueous phase extracted with ethyl acetate (EtOAc). The combined organic phases were evaporated. The crude product (0.465 g) was obtained as a pale white solid and used as such in the next step.

LC-MS (M+H): 337.9.

H NMR (400 MHz, CDCI₃), δ 1 ,58 (s, 6 H), 3,0 (s, 3 H), 3,37 (s, 3H), 7,13 (d, 1 H).

Step 4: 2,4-dichloro-3-[2-(dimethylamino)-1 ,1 -dimethyl-2-oxo-ethoxy]-6-fluoro-N-(1 - methyltetrazol-5-yl)benzamide

2,4-dichloro-3-[2-(dimethylamino)-1 ,1 -dimethyl-2-oxo-ethoxy]-6-fluoro-benzoic acid (0.465 g, 0.001 mol) was dissolved in 5 mL methylene chloride. 1 drop DMF was added. Then oxalyl chloride (0.349 g, 0.003 mol) was added at 0°C. After stirring overnight at 25°C the volatiles were evaporated. The residue was suspended in 20 mL THF and added at -75°C to a solution prepared in the following manner: 1 -methyltetrazol-5-amine (0.272 g, 0.003 mol) was dissolved in anhydrous THF (7.8 mL) and cooled to -70°C. A solution of methyl lithium in THF (3 molar, 0.003 mol) was added dropwise at this temperature and the reaction mixture warmed up to -5 °C and kept for 0.5 h. After 0.5 h at -75°C the reaction mixture was quenched with brine and 1 .5 mL 2 N hydrochloric acid. The organic phase was washed again with brine and 1 mL 2 N hydrochloric acid and finally again with brine. The organic phase was evaporated and the crude prod- uct purified by column chromatography to yield 0.194 g of a pale white solid.

LC-MS (M+H): 419.

H NMR (400 MHz, d₆-DMSO), δ 1 ,48 (s, 6 H), 2,87 (s, 3 H), 3,27 (s, 3H), 3,95 (s, 3H), 7,82 (d, 1 H), 12,18 (br s, 1 H). Example 2: [2,6-dichloro-4-fluoro-3-[(1 -methyltetrazol-5-yl)carbamoyl]phenyl] (2S,6R)-2,6- dimethylmorpholine-4-carboxylate (Compound I.A.V.4 of Table 4)

Step 1 : 2-benzyloxy-1 ,3-dichloro-5-fluoro-benzene

Commercially available 2, 6-dichloro-4-fluoro-phenol (CAS 392-71 -2, 198.0 g, 1 .077 mol) was dissolved in acetone (1600 ml_). Powdered potassium carbonate (148.8 g, 1.077 mol) was suspended in this solution. Benzylbromide (282.5 g, 1.077 mol) was dosed to the suspension over 40 min with slight self-heating up to 31 °C. After 6 h at 25°C most of the acetone was evap- orated. Progress of the conversion could be monitored by HPLC. Water (2 L) was added to the residue. The precipitated crude product was redissolved in methylene chloride. After washing the solution with water the organic phase was separated, dried over magnesium sulfate and evaporated to yield 282.5 g of the product as a pale white solid.

H NMR (400 MHz, de-DMSO), δ 4,98 (s, 2 H), 7,36 - 7,45 (m, 3H), 7,52 (d, 2H),

7,57 (d, 2 H).

Step 2: 3-benzyloxy-2,4-dichloro-6-fluoro-benzoic acid

2-benzyloxy-1 ,3-dichloro-5-fluoro-benzene (0.6 g, 0.002 mol) was dissolved in 2 L THF and cooled to -70°C, when 625 ml. of a 1.6 molar solution of n-butyllithium in n-hexane were dosed such that the temperature remains between -69°C and -73°C. After a post-dosage time of 1 h at -74°C carbon dioxide gas (100 g, 2.27 mol) was passed into the solution over 30 min keeping the temperature between -63°C and -72°C. Then the external cooling was removed and the reaction mixture was left to warm up to 6°C forming a thick suspension. At 6°C 300 ml. of a 5 wt-% hydrochloric acid were added under further warm-up to 16°C. The pH of the water phase should be at pH 1 -3. The aqueous phase was separated and extracted once with methyl tert- butylether (MTBE). The combined organic phases were washed with brine and then evaporated. The crude product was redissolved in a 10 wt-% sodium hydroxide solution and extracted two times with toluene. The aqueous phase was acidified to pH 1 -3 and extracted two times with ethyl acetate (EtOAc).The combined organic phases were washed with water and evaporated. The residue was redissolved in toluene and again evaporated to yield 168.8 g of the product azeotropically dried as a pale white solid.

H NMR (400 MHz, de-DMSO), δ 5,00 (s, 2 H), 7,34 - 7,44 (m, 3H), 7,50 (d, 2H), 7,73 (d, 1 H), 8-12 (br s, 1 H).

Step 3: 3-benzyloxy-2,4-dichloro-6-fluoro-benzoyl chloride

3-benzyloxy-2,4-dichloro-6-fluoro-benzoic acid (60 g, 0.19 mol) was dissolved in 480 ml_ toluene. Thionylchlorid (100 ml_, 1 .37 mol) was dosed at 80°C. After stirring overnight at 80°C the volatiles and the crude product was obtained as a yellow wax and used as such in the next step.

H NMR (400 MHz, CDCI₃), δ 5,02 (s, 2 H), 7,23 (d, 2H), 7,34 - 7,45 (m, 3H), 7,52 (d, 1

H).

Step 4: 3-benzyloxy-2,4-dichloro-6-fluoro-N-(1 -methyltetrazol-5-yl)benzamide

1 -Methyltetrazol-5-amine (37.7 g, 0.381 mol) was dissolved in anhydrous THF (940 mL) and cooled to -70°C. A solution of methyl lithium in THF (3 molar, 0.003 mol) was added drop- wise at this temperature and then reaction mixture was warmed up to -5 °C. After 0,5 h the reaction mixture was cooled again to -75°C and the solution of 3-benzyloxy-2,4-dichloro-6-fluoro- benzoyl chloride in 100 mL THF was added forming a sticky solid. The suspension was diluted with additional 100 mL THF, warmed up to 25°C, stirred overnight and then quenched once with 200 mL 2 N hydrochloric acid and three times with 50 mL 2 N hydrochloric acid containing 5 g NaCI to improve phase separation. The organic phase was dried over Na2S0₄ and evaporated to yield 73.5 g product as a pale white solid, which was used as such in the next step.

LC-MS (M+H): 396.

H NMR (400 MHz, d₆-DMSO), δ 4,0 (s, 3H), 5,15 (s, 2 H), 7,36 - 7,48 (m, 3H), 7,55 (d, 2H), 7,87 (d, 1 H), 12,2 (s, 1 H).

Step 5: 2,4-dichloro-6-fluoro-3-hydroxy-N-(1 -methyltetrazol-5-yl)benzamide

3-benzyloxy-2,4-dichloro-6-fluoro-N-(1 -methyltetrazol-5-yl)benzamide (73.5 g, 0.186 mol) was dissolved in acetic acid. After adding 176 g of cone, hydrochloric acid the mixture was heated to reflux (98°C) and kept at reflux for 5.5 h. After cooling to 25°C and stirring overnight the precipitated solid was filtered, washed with acetic acid and finally with methyl tert. -butyl ether. After drying at 40°C under vacuum 42.4 g of the product were obtained as a pale white solid.

LC-MS (M+H): 305,9.

H NMR (400 MHz, de-DMSO), δ 3,97 (s, 3H), 7,70 (d, 1 H), 1 1 ,67 (br s, 1 H), 12,1 (s,

1 H). Step 6: [2,6-dichloro-4-fluoro-3-[(1 -methyltetrazol-5-yl)carbamoyl]phenyl] (2S,6R)-2,6- dimethylmorpholine-4-carboxylate

2,4-dichloro-6-fluoro-3-hydroxy-N-(1 -methyltetrazol-5-yl)benzamide (15 g, 0.049 mol) was dissolved in 30 ml. dimethylformamide (DMF). Powdered potassium carbonate (13.55 g, 0.098 mol) was suspended in this solution. 2,6-cis-dimethylmorpholin-4-carbonyl chloride (9.6 g, 0.051 mol) was dropped to the suspension over 15 min at 25°C. After stirring overnight the mixture was heated up to 60°C for 1 h. DMF was evaporated at 50°C and water was added to the residue. Small amounts of not dissolved material was filtered off. The alkaline aqueous solution was extracted with methylene chloride and then the pH was adjusted to pH 8-9, when product pre- cipitation occurred. The precipitated product was dried at 50°C under vacuum. Thus 12.0 g of the product were obtained as a pale white solid.

LC-MS (M+H): 447.0.

H NMR (400 MHz, d₆-DMSO), δ 1 ,12 (m, 6H), 2,65 (t, 1 H), 2,85 (t, 1 H), 3,75 (m, 2H), 3,82 (d, 1 H), 3,97 (s, 3H), 4,08 (d, 1 H), 7,70 (d, 1 H), 12,3 (br s, 1 H).

Example 3: 2,4-dichloro-3-[2-(dimethylamino)-2-oxo-ethoxy]-6-fluoro-N-(1 -methyltetrazol- 5-yl)benzamide (Compound I.A.V.13 of Table 4)

2,4-dichloro-6-fluoro-3-hydroxy-N-(1 -methyltetrazol-5-yl)benzamide (15 g, 0.049 mol) was dissolved in 20 ml. dimethylformamide (DMF). Powdered potassium carbonate (13.55 g, 0.098 mol) was suspended in this solution. 2-chlor-N,N-dimethylacetamide (9.6 g, 0.051 mol) was dropped to the suspension over 15 min at 25°C. After stirring overnight the mixture was evaporated at 70°C. Water (50 ml.) and methylene chloride (30 ml.) were added to the residue. After separation of the organic phase the alkaline aqueous solution was extracted three times with methylene chloride (3 x 25 ml.) and then the pH was adjusted to pH 7, when product precipitation occurred. The precipitated product was dried at 50°C under vacuum. Thus, 9.7 g of the product were obtained as a pale white solid.

LC-MS (M+H): 391.0.

H NMR (400 MHz, d₆-DMSO), δ 2,86 (s, 3H), 3,0 (t, 3H), 3,94 (s, 3H), 4,72 (s, 2H), 7,82 (d, 1 H), 12,28 (br s, 1 H).

By analogy to the methods described in Examples 1 to 3 the following compounds of the formula I. A' of Table C were prepared. The compounds of formula I. A' are compounds of formula I.A.V, wherein R⁵ is fluorine.

Table C:

No. according R R³ R⁵ R2 LC-MS to Table 5 (M+H)

I.A.V.3452 CI CI F 487

I.A.V.3453 CI CI F 459

0

I.A.V.3443 CI CI F 530 ^Y 0 ^N^^CF3

I.A.V.3446 CI CI F 447

0

I.A.V.2519 CI I F 469

0

By analogy to the methods described above the following compounds of the formula I.A" of Table D were prepared. The compounds of formula I.A" are compounds of formula I.A.XII, wherein R⁵ is fluorine.

Table D:

No. according R R³ R⁵ R2 LC-MS to Table 5 (M+H)

I.A.XII.13 CI CI F 377

0

By analogy to the methods described above the following compounds of the formula I.A'" of Table E were prepared. The compounds of formula I.A'" are compounds of formula I.A.VI, wherein R⁵ is fluorine.

(I.A'")

Table E:

By analogy to the methods described above the following compounds of the formula I.A"" of Table F were prepared. The compounds of formula I.A"" are compounds of formula I.A.IX, wherein R⁵ is fluorine.

Table F:

No. according R R³ R⁵ R2 LC-MS to Table 5 (M+H)

I.A.IX.4 CI CI F 0 475

V By analogy to the methods described in Examples 1 to 4 the following compounds of the formula I.B' of Table G were prepared. The compounds of formula I.B' are compounds of formula I.B.V, wherein R⁵ is fluorine.

Table G:

By analogy to the methods described above the following compounds of the formula I.C of Table H were prepared. The compounds of formula I.C are compounds of formula I.C.V, wherein R⁵ is fluorine.

Table H:

By analogy to the methods described above the following compounds of the formula I.D' of Table I were prepared. The compounds of formula I.D' are compounds of formula I.D.V, wherein R⁵ is fluorine.

Table I:

II. 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. 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. At an application rate of 250g/ha the following compounds were tested in post-emergence tests against ALOMY (Alopecurus myosuroiedes), ECHCG (Echinocloa crus-galli), AMARE (Amaranthus retroflexus) and CHEAL (Chenopodium album) and showed a control of at least 85%:

Compounds I.A.V.1 , I.A.V.4, I.A.V.5, I.A.V.7, I.A.V.9, I.A.V.336, I.A.V.502, I.A.V.167,

I.A.V.170, I.A.V.668, I.A.V.665, I.A.V.13, I.A.V.29, I.A.V.19, I.A.V.24, I.A.V.25, I.A.V.26, I.A.V.27, I.A.V.28, I.A.V.179, I.A.V.195, I.A.V.30, I.A.V.31 , I.A.V.34, I.A.V.36, I.A.V.38, I.A.V.40, I.A.V.41 , I.A.V.42, I.A.V.43, I.A.V.361 , I.A.V.193, I.A.V.185, I.A.V.191 , I.A.V.2491 , I.A.V.3423, I.A.V.3421 , I.A.V.53, I.A.V.3427, I.A.V.83, I.A.V.79, I.A.V.3433, I.A.V.3434, I.A.V.3429, I.A.V.3435, I.A.V.3430, I.A.V.3437, I.A.V.3439, I.A.V.3455, I.A.V.3445, I.A.V.3451 , I.A.V.3447, I.A.V.2515, I.A.V.3450, I.A.V.3446, I.A.VI.4, I.B.V.4, I.B.V.29 and I.B.V.13.

Claims

1 . A compound of formula I ,

wherein

(Q¹) (Q²) (Q³) (Q⁴) ; 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, d-Cs-alkyl, C2-C8- alkenyl, C2-C8-alkynyl, C-i-Cs-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4 alkyl, Ci-C₈-alkoxy, Ci-C₄-alkoxy-Ci-C₄-alkoxy-Z¹-, Ci-C₆-haloalkoxy, R^1b-S(0)_k-Z¹-; is a radical of the formul

R³ is selected from the group consisting of hydrogen, cyano, thiocyanato, halogen, nitro, hydroxy-Z³-, Ci-C6-alkyl, C2-Cs-alkenyl, C2-Cs-alkynyl, C3-Cio-cycloalkyl-Z³-, C3-C6- cycloalkenyl-Z³-, C3-Cio-cycloalkoxy-Z³-, C3-Cio-cycloalkyl-Ci-C2-alkoxy, where the cyclic groups of the four aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C4-cyanoalkyl, Ci-Cs-haloalkyI, C2-C8-haloalkenyl, Cs-Cs-haloalkynyl, Ci-

Cs-alkoxy-Z³-, Ci-Cs-haloalkoxy-Z³-, Ci-C4-alkoxy-Ci-C4-alkoxy-Z³-, Ci-C4-haloalkoxy-Ci- C4-alkoxy-Z³-, C2-Cs-alkenyloxy-Z³-, C2-Cs-alkynyloxy-Z³-, C2-Cs-haloalkenyloxy-Z³-, C3- Cs-haloalkynyloxy-Z³-, R^3b-S(0)_k-Z³-, R^3c-C(0)-Z³-,

R^3dO-C(0)-Z³-, R^3dO-N=CH-Z³-, R^3eR^3fN-C(0)-Z³-, R¾R^3hN-Z³-, R²²C(0)0-Z³-,

R²⁵OC(0)0-Z³-, (R²²)₂NC(0)0-Z³-, R²⁵S(0)₂0-Z³-, R²²OS(0)₂-Z³-, (R²²)₂NS(0)₂-Z³-, R²⁵OC(0)N(R²²)-Z³-, (R²²)₂NC(0)N(R²²)-Z³-, (R²²)₂NS(0)₂N(R²²)-Z³-, (OH)₂P(0)-Z³-, (Ci- C4-alkoxy)₂P(0)-Z³-, phenyl-Z^3a-, heterocyclyl-Z^3a-, 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 cyclic groups in phenyl-Z^3a- and heterocyclyl-Z^3a- 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, Ci-Cs-alkyl, ni- tro, C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C₂- Cs-alkenyl, C₂-Cs-alkynyl, Ci-Cs-haloalkyl, Ci-C3-alkylamino, Ci-C3-dialkylamino, C1-C3- alkylamino-S(0)k, Ci-C3-alkylcarbonyl, Ci-Cs-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, C1-C4- alkoxy-Ci-C4-alkoxy-Z¹-, Ci-C4-alkylthio-Ci-C4-alkylthio-Z¹-, C₂-C6-alkenyloxy, C₂-C6- alkynyloxy, C C₆-haloalkoxy, Ci-C4-haloalkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4- alkoxy-Z¹-, R^1b-S(0)_k-Z¹-, phenoxy-Z¹- and heterocyclyloxy-Z¹-, where heterocydyloxy 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 heterocydyloxy are unsubstituted or substituted by 1 , 2, 3 or 4 groups R¹¹, which are identical or different;

R⁵ is halogen, cyano-Z¹-, nitro, Ci-Cs-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C4- alkyl, where the C₃-C₇-cycloalkyl groups in the two aforementioned radicals are

unsubstituted or partially or completely halogenated, C₂-Cs-alkenyl, C₂-Cs-alkynyl, Ci-Cs- haloalkyl, Ci-C3-alkylamino, Ci-C3-dialkylamino, Ci-C3-alkylamino-S(0)k, C1-C3- alkylcarbonyl, Ci-Cs-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy-Z¹-, Ci-

C₄-alkylthio-Ci-C₄-alkyl, Ci-C₄-alkylthio-Ci-C₄-alkylthio-Z¹-, C₂-C₆-alkenyloxy, C₂-C₆- alkynyloxy, C C₆-haloalkoxy, Ci-C4-haloalkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4- alkoxy-Z¹-, R^1b-S(0)_k-Z¹-, phenoxy-Z¹- and heterocyclyloxy-Z¹-, where heterocydyloxy is an 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 heterocydyloxy are unsubstituted or substituted by 1 , 2, 3 or 4 groups R¹¹, which are identical or different;

R^6a, R^6b, R^6c, R^6d are, independently of each other, selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7- cycloalkyl groups of the two aforementioned radicals are unsubstituted or partially or com- pletely halogenated, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C2-C6-haloalkenyl, C₃- Ce-haloalkynyl, Ci-C₄-alkoxy-Ci-C₄-alkyl, Ci-C₄-haloalkoxy-Ci-C-alkyl, R^b-S(0)_n-Ci-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, C C₄-alkyl, C C₄-haloalkyl, C C₄-alkoxy and C C₄-haloalkoxy;

R¹¹, R²¹ independently of each other are selected from the group consisting of cyano, halogen, nitro, Ci-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-halocycloalkyl, Ci-C₆-haloalkyl, C₂-C₆- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C6-alkoxy, Ci-C₄-alkoxy- Ci-C₄-alkyl, Ci-C₄-alkylthio-Ci-C₄-alkyl, Ci-C₄-haloalkoxy-Ci-C₄-alkyl, Ci-C₄-alkoxy-Ci-C₄- alkoxy, C₃-C₇-cycloalkoxy and Ci-C₆-haloalkoxy, or two radicals R²¹ bound to the same carbon atom together may form a group =0;

Z is a covalent bond or linear Ci-C₄-alkanediyl,

Z¹, Z³ independently of each other are selected from the group consisting of a covalent bond and Ci-C₄-alkanediyl, which is unsubstituted, partly or completely fluorinated;

Z² is a covalent bond or a bivalent radical selected from Ci-C₄-alkanediyl and Ci-C₄- alkanediyl-0-Ci-C₄-alkanediyl,

where in the last two mentioned radicals the Ci-C₄-alkanediyl groups are linear and

unsubstituted, or partly or completely fluorinated or substituted by 1 , 2, 3 or 4 groups

R^z,

Z^3a is selected from the group consisting of a covalent bond, Ci-C₄-alkanediyl, 0-Ci-C₄- alkanediyl, Ci-C₄-alkanediyl-0 and Ci-C₄-alkanediyl-0-Ci-C₄-alkanediyl;

R^z are identical or different and selected from the group consisting of Ci-C6-alkyl, C3-C7- cycloalkyl, C₃-C₇-cycloalkyl-Ci-C-alkyl, where the C₃-C₇-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated,

Ci-C6-haloalkyl, Ci-C6-alkoxy, C2-C6-alkenyl, Ci-C₄-alkyl-C2-C6-alkenyl, C2-C6-haloalkenyl, C₂-C₆-alkynyl, C₃-C₆-haloalkynyl, Ci-C-alkoxy-Ci-C-alkyl, Ci-C-alkyl-S(0)_n-Ci-C-alkyl, Ci-C₄-alkylamino-Ci-C₄-alkyl, Ci-C₄-dialkylamino-Ci-C₄-alkyl, Ci-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, Ci-C₄-alkyl, Ci-C₄- haloalkyl, Ci-C₄-alkoxy and Ci-C₄-haloalkoxy; R^2a is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, C3- C₇-cycloalkyl-Ci-C4-alkyl, where the C3-C₇-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated,

Ci-C6-haloalkyl, Ci-C6-alkoxy, C2-C6-alkenyl, Ci-C4-alkyl-C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl,

Ci-C4-alkyl-S(0)_n-Ci-C4-alkyl, Ci-C4-alkylamino-Ci-C4-alkyl, Ci-C4-dialkylamino-Ci-C4- alkyl, Ci-C₆-c anoalkyl, R^3c-C(0)-Ci-C₄-alkyl, R^MO-C(0)-Ci-C₄-alkyl, R^3eR^3fN-C(0)-Ci-C₄- alkyl, R^3eR^3fNS(0)2-Ci-C₄-alkyl, 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 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, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;

R^2b is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, C3- C₇-cycloalkyl-Ci-C4-alkyl, where the C3-C₇-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated,

Ci-C4-alkyl-S(0)_n-Ci-C4-alkyl, Ci-C4-alkylamino-Ci-C4-alkyl, Ci-C4-dialkylamino-Ci-C4- alkyl, Ci-C₆-cyanoalkyl, R^3c-C(0)-Ci-C₄-alkyl, R^3dO-C(0)-Ci-C₄-alkyl,

alkyl, R^3eR^3fNS(0)₂-Ci-C₄-alkyl, 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 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, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; or

R^2a, R^2b together with the nitrogen atom, to which they are bound may form a 4-, 5-, 6-, 7- or 8-membered, saturated or partially unsaturated heteromonocyclic radical or may form a 6-, 7-, 8-, 9- or 10-membered, saturated or partially unsaturated heterobicydic radical , where the heteromono- or heterobicydic radical may contain as a ring member a further heteroatom selected from O, S and N and where the heteromono- or heterobicydic radical is unsubstituted or carries 1 , 2, 3 or 4 groups R^2e or carries 1 group R^2f and 0, 1 , 2 or 3 groups R^2e,

R^2c is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, C3- C₇-cycloalkyl-Ci-C4-alkyl, where the C3-C₇-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated,

R^2d can be bound to each saturated carbon atom of the radical of formula 2b and is selected from the group consisting of halogen, Ci-C4-alkyl and C|-C₄-haloalkyl; R^2e are identical or different and selected from the group consisting of halogen, CN, Ci-

C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;

R^2f is selected from the group consisting of =0, R^4b-S(0)_k-Z⁴-, R^4c-C(0)-Z⁴- R^4dO-C(0)-Z⁴-, R^4eR^4fN-C(0)-Z⁴-,

R^b, R^1b, R^3b, R^4b independently of each other are selected from the group consisting of Ci-C6-alkyl, C3-C7-cycloalkyl, Ci-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, Ci-C₄-alkyl, Ci-C₄-haloalkyl, Ci-C₄-alkoxy and Ci-C₄-haloalkoxy;

R^3c, R^4c independently of each other are selected from the group consisting of hydrogen, Ci-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-Ci-C₄-alkyl, where the C3-C7- cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C₆-haloalkyl, Ci-C₆-alkoxy, C₂-C₆-alkenyl, Ci-C₄-alkyl-C2-C₆- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci- C4-alkyl-S(0)_n-Ci-C4-alkyl, Ci-C4-alkylamino-Ci-C4-alkyl, Ci-C4-dialkylamino-Ci-C4-alkyl, Ci-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, Ci-C₄-alkyl, Ci-C₄-haloalkyl, Ci-C₄-alkoxy and C1-C4- haloalkoxy;

R^3d, R^4d independently of each other are selected from the group consisting of hydrogen, Ci-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-Ci-C₄-alkyl, where the C₃-C₇- cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C₆-haloalkyl, Ci-C₆-alkoxy, C₂-C₆-alkenyl, Ci-C₄-alkyl-C₂-C₆- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C₄-alkoxy-Ci-C₄-alkyl, Ci- C₄-alkyl-S(0)_n-Ci-C₄-alkyl, Ci-C₄-alkylamino-Ci-C₄-alkyl, Ci-C₄-dialkylamino-Ci-C₄-alkyl, Ci-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, Ci-C₄-alkyl, Ci-C₄-haloalkyl, Ci-C₄-alkoxy and Ci-C₄- haloalkoxy; R^3e, R^3f, R^4e, R^4f independently of each other are selected from the group consisting of hydrogen, Ci-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-Ci-C₄-alkyl, where the C₃-C₇- cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₃-C6-haloalkynyl, Ci-C₄-alkoxy-Ci-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, Ci-C₄-alkyl, Ci-C₄-haloalkyl, Ci-C₄-alkoxy and Ci-C₄-haloalkoxy; or

R^3e and R^3f or R^4e and R^4f 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 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 =0, halogen, Ci-C₄-alkyl, Ci-C₄-haloalkyl, Ci-C₄-alkoxy and Ci-C₄-haloalkoxy;

R¾, R⁴9 independently of each other are selected from the group consisting of hydrogen, Ci-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-Ci-C₄-alkyl, where the C₃-C₇- cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₃-C₆-haloalkynyl, Ci-C₄-alkoxy-Ci-C₄-alkyl, Ci-C₄-alkylsulfonyl, Ci-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, Ci-C₄-alkyl, Ci-C₄-haloalkyl, Ci-C₄-alkoxy and Ci-C₄-haloalkoxy;

R^3h, R^4h independently of each other are selected from the group consisting of hydrogen, Ci-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-Ci-C₄-alkyl, where the C₃-C₇- cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, d-Ce-haloalkyl, C₂-C₆-alkenyl, C2-C₆-haloalkenyl, C₂-C₆-alkynyl, C₃-C₆-haloalkynyl, Ci-C₄-alkoxy-Ci-C₄-alkyl, Ci-C -alkylsulfonyl, Ci-C -alkylcarbonyl, a radical C(0)R^k, 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, Ci-C -alkyl, Ci-C -haloalkyl, Ci-C -alkoxy and Ci-C - haloalkoxy; or

R¾ and R^3h or R⁴9 and R^4h 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 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 =0, halogen, Ci-C₄-alkyl, Ci-C₄-haloalkyl, Ci-C₄- alkoxy and Ci-C₄-haloalkoxy; R²² is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-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-Ci-C6-alkyl, Ci-C6-alkoxy-Ci-C6-alkyl, Cs-Ce-cycloalkyl-Ci-Ce-alkoxy-Ci-Ce-alkyl, phenyl-Z¹, phenyl-0-Ci-C₆-alkyl, phenyl-N(R²³)- d-Ce-alkyl, phenyl-S(0)_n-Ci-C₆-alkyl, heterocyclyl-Z¹, heterocyclyl-N(R²³)-Ci-C₆-alkyl, heterocyclyl-0-Ci-C6-alkyl, heterocyclyl-S(0)_n-Ci-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, 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, Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-cycloalkyl,

C(0)OR²³, C(0)N(R²³)₂, OR²³, N(R²³)₂, S(0)_nR²⁴, S(0)₂OR²³, S(0)₂N(R²³)₂, and R²³0-Ci- C6-alkyl, and where heterocyclyl bears 0, 1 or 2 oxo groups;

R²³ is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C₂- C6-alkenyl, C₂-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, and phenyl;

R²⁴ is selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C₂-C6-alkenyl, C₂-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, and phenyl; R²⁵ is selected from the group consisting of Ci-C6-alkyl, Ci-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-Ci-C6-alkyl, Ci-C6-alkoxy-Ci-C6-alkyl, C3-C6- cycloalkyl-Ci-C₆-alkoxy-Ci-C₆-alkyl, phenyl-Z¹, phenyl-0-Ci-C₆-alkyl, phenyl-N(R²³)-Ci-C₆- alkyl, phenyl-S(0)_n-Ci-C₆-alkyl, heterocyclyl-Z¹, heterocyclyl-N(R²³)-Ci-C₆-alkyl, heterocyclyl-0-Ci-C6-alkyl, heterocyclyl-S(0)_n-Ci-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, 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, Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-cycloalkyl,

C(0)OR²³, C(0)N(R²³)₂, OR²³, N(R²³)₂, S(0)_nR²⁴, S(0)₂OR²³, S(0)₂N(R²³)₂, and R²³0-Ci- C6-alkyl, and where heterocyclyl bears 0, 1 or 2 oxo groups; k is 0, 1 or 2; n is 0, 1 or 2; p is 0, 1 or 2; and

R^k has the meanings of R^3c; or an N-oxide or an agriculturally suitable salt thereof.

The compound of claim 1 , where Q is Q¹.

The compound of claim 1 , where Q is Q².

The compound of claim 1 , where Q is Q³.

The compound of claim 1 , where Q is Q⁴.

The compound of any one of the preceding claims, where R¹ is selected from the group consisting of halogen, nitro, cyano Ci-C4-alkyl, Ci-C4-haloalkyl,

Ci-C₄-alkoxy-Ci-C₄-alkoxy-Z¹- and R^1b-S(0)_k-Z¹-.

The compound as claimed in claim 6, where R¹ is selected from the group consisting of halogen and Ci-C₄-alkyl.

The compound of any one of the preceding claims, where R² is a radical of the formula 2a The compound as claimed in claim 8, where

Z² is a bond, linear Ci-C3-alkandiyl, which is unsubstituted or partly or completely fluor- inated or which carries 1 , 2, 3 or 4 methyl groups;

R^2a is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C3- C6-cycloalkyl, benzyl and heterocyclylmethyl, where benzyl 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, Ci-C -alkyl, Ci-C -haloalkyl, Ci-C -alkoxy and Ci C₄-haloalkoxy; R^2b is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C3- C7-cycloalkyl, C3-C7-cycloalkyl-methyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, d-Ce-alkoxy, Ci-C₄-alkoxy-Ci-C₄-alkyl, Ci-C -alkoxy-Ci-C -alkoxy, Ci-C₄-alkyl-S(0)_n-Ci- C₄-alkyl, Ci-C -alkyl-C(0)-Ci-C -alkyl, Ci-C -alkyl-0-C(0)-Ci-C -alkyl, (Ci-C -alkyl)₂N- C(0)-Ci-C₄-alkyl, phenyl, benzyl, heterocyclyl and heterocyclylmethyl, 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, Ci-C₄-alkyl, Ci-C₄- haloalkyl, Ci-C₄-alkoxy and Ci-C₄-haloalkoxy;

or

R^2a, R^2b together with the nitrogen atom, to which they are bound form a 5-, 6-, 7- or 8- membered, saturated heteromonocyclic radical or form a 7-, 8-, 9- or 10-membered saturated heterobicyclic radical, where the heteromonocyclic or heterobicycic radical may contain as a ring member a further heteroatom selected from O, S and N and where the heteromonocyclic or heterobicycic radical is unsubstituted or carries 1 , 2, 3 or 4 groups R^2e or carries 1 group R^2f and 0, 1 , 2 or 3 groups R^2e, where

R^2e is selected from the group consisting of halogen and Ci-C₄-alkyl and the group R^2f is selected from R^4c-C(0)-, R^4dO-C(0)- and R^4eR^4fN-C(0)-, where R^4c, R^4d, R^4e and R^4f, independently of each other are Ci-C₄-alkyl or Ci-C₄-haloalkyl.

The compound as claimed in claim 9, where

Z² is a bond, CH₂, CH(CH₃), C(CH₃)₂ or CF₂;

R^2a is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C3- C6-cycloalkyl, benzyl and heterocyclylmethyl, where heterocyclyl is a 5- or 6-membered heteroaromatic radical containing 1 , 2 or 3 heteroatoms selected fom the group consisting of N and O as ring members, where benzyl 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, Ci-C -alkyl, Ci-C -haloalkyl, Ci-C -alkoxy and Ci-C - haloalkoxy;

R^2b is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C3-haloalkyl, C3- Ce-cycloalkyl, Ci-C -alkoxy, Ci-C -alkyl-0-C(0)-Ci-C -alkyl, (Ci-C -alkyl)₂N-C(0)-Ci-C - 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, Ci-C₄-alkyl and Ci-C₄-alkoxy;

or

R^2a, R^2b together with the nitrogen atom, to which they are bound form a 5-, 6- or 7- membered, saturated heteromonocyclic radical or form a 7-, 8-, 9- or 10-membered saturated heterobicyclic radical, where the heterobicycic radical is a fused or a bridged ring sys- tem, where the heteromonocyclic or heterobicycic radical may contain as a ring member a further heteroatom selected from O and N and where the heteromonocyclic or heterobicycic radical is unsubstituted or carries 1 , 2, 3 or 4 groups R^2e or carries 1 group R^2f and 0, 1 , 2 or 3 groups R^2e, where

R^2e is Ci-C₄-alkyl; and

The compound of any one of claims 1 to 7, where R² is a radical of the formula 2b.

The compound of claim 1 1 , where

Z is CH₂, CHzCHz or CHzCHzCHz;

R^2c is selected from the group consisting of hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl, p is 0, 1 or 2.

and

R^2d is selected from the group consisting of methyl and fluorine.

The compound of claim 12, where

Z is CH₂, CHzCHz or CHzCHzCHz;

R^2c is selected from the group consisting of hydrogen, Ci-C₄-alkyl and Ci-C3-haloalkyl; and

p is 0.

The compound of any one of the preceding claims, where R³ is selected from the group consisting of halogen, nitro, Ci-C6-alkyl, Ci-Cs-haloalkyl, d-Cs-haloalkoxy-Z³, and R^3b-S(0)_k-Z³. 15. The compound of claim 14, where R³ is selected from the group consisting of halogen, Ci- C₄-haloalkyl, Ci-C₄-alkylthio and Ci-C₄-alkylsulfonyl.

16. The compound of any one of the preceding claims, where R⁴ is hydrogen. 17. The compound of any one of the preceding claims, where R⁵ is halogen; in particular F.

18. The compound of any one of the preceding claims, where R^6a, R^6b, R^6c, R^6d are, independently of each other selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci- C₄-alkoxy-Ci-C₄-alkyl, and phenyl.

19. The compound of claim 18, where R^6a, R^6b, R^6c, R^6d are, independently of each other, selected from the group consisting of hydrogen and Ci-C₄-alkyl. The compound of any one of the preceding claims, which is selected from the compound of

(I. A')

where R^6a is methyl, R⁴ is hydrogen, R⁵ is F and the combinations of R¹, R² and R³ are as given in lines 1 to 121 of the following table I. A; co

(I. A")

where R^6a is hydrogen, R⁴ is hydrogen, R⁵ is F and the combinations of R¹, R² and R³ are as given in lines 4 and 20 of the following table I.A co

(I.A'")

where R^6a is ethyl, R⁴ is hydrogen, R⁵ is F and the combination of R¹, R² and R³ is as given in line 4 of the following table I.A; co

(I.A"")

where R^6a is n-propyl, R⁴ is hydrogen, R⁵ is F and the combination of R¹, R² and R³ is as given in line 4 of the following table I.A; compounds of the formula (I.B)

where R^6b is methyl, R⁴ is hydrogen, R⁵ is F and the combination of R¹, R² and R³ are as given in lines 1 to 3 of the following table I.B; c mpounds of the formula (I.C)

where the combination of R¹, R² and R³ is as given in line 4 of the following table I. A; and com ounds of the formula (I.D)

where the combination of R¹, R² and R³ is as given in line 4 of the following table I. A; where in tables I. A and I.B the arrow indicates the point of attachment of R² to the oxygen atom in formulae I .A', I .A", I.A'", I.A"", I.B, I.C and I.D, respectively:

Table I.A

R R² R³

the N-oxides and the agriculturally suitable salts thereof.

21 . A composition comprising at least one compound as claimed in any one of claims 1 to 20, an N-oxide or an agriculturally suitable salt thereof, and at least one auxiliary, which is customary for formulating crop protection compounds.

22. The use of a compound as claimed in any one of claims 1 to 20, an N-oxide or an agriculturally suitable salt thereof, or of the composition of claim 21 for controlling unwanted vegetation.