halogen-substituted compounds

• US 20110301181A1
• Filed: 10/27/2009
• Published: 12/08/2011
• Est. Priority Date: 11/05/2008
• Status: Active Grant

• Current Assignee: Bayer Intellectual Property GmbH (Bayer AG)
• Original Assignee: Bayer Cropscience AG (Bayer AG)
• Inventors: Adelt, Isabelle, Giencke, Wolfgang, Heil, Markus, Jeschke, Peter, Krüger, Bernd-Wieland, Mühlthau, Friedrich August, Sudau, Alexander, Raming, Klaus, Ebbinghaus-Kintscher, Ulrich, Adamczewski, Martin, Voerste, Arnd, Görgens, Ulrich, Kapferer, Tobias, Drewes, Mark Wilhelm, Becker, Angela, Maue, Michael, Franken, Eva-Maria
• Granted Patent: US 8,946,234 B2
• Time in Patent Office: Days
• US Class Current: 514/256
• CPC Class Codes: A01N 43/40 six-membered rings
• CPC Class Codes: A01N 43/54 1,3-Diazines; Hydrogenated 1,3-diazines
• CPC Class Codes: A01N 43/56 1,2-Diazoles; Hydrogenated 1,2-diazoles
• CPC Class Codes: A01N 43/78 1,3-Thiazoles; Hydrogenated 1,3-thiazoles
• CPC Class Codes: A61P 33/00 Antiparasitic agents
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: C07D 213/81 Amides; Imides
• CPC Class Codes: C07D 231/14 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 231/16 Halogen atoms or nitro radicals
• CPC Class Codes: C07D 231/20 One oxygen atom attached in position 3 or 5
• CPC Class Codes: C07D 239/28 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
• CPC Class Codes: C07D 239/34 One oxygen atom
• CPC Class Codes: C07D 277/56 Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
• CPC Class Codes: C07D 401/12 linked by a chain containing hetero atoms as chain links

Abstract

The invention relates to compounds of the general formula (I),

in which the radicals A₁, A₂, A₃, A₄, Lm, Q, R¹, T and U have the meaning given in the description and to the use of the compounds for controlling animal pests. In addition, the invention relates to processes and intermediates for the preparation of the compounds according to formula (I).

Claims

1. A method of controlling an animal pest comprising contacting said animal pest or a habitat thereof with a compound of formula (I)

2. The method according to claim 1 wherein

R¹ is hydrogen or one of optionally substituted groups C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₇-cycloalkyl, C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl, cyano-C₁-C₂-alkyl, aryl(C₁-C₃)-alkyl, or heteroaryl(C₁-C₃)-alkyl;

A₁ is CR² or nitrogen,

A₂ is CR³ or nitrogen,

A₃ is CR⁴ or nitrogen, and

A₄ is CR⁵ or nitrogen,

wherein at most three of the chemical groups A₁ to A₄ are nitrogen at the same time, and wherein

R², R³, R⁴ and R⁵, independently of one another, are hydrogen, halogen, CN, NO₂, optionally substituted C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-haloalkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₆-haloalkylsulphonyl, C₁-C₆-alkylamino, N,N-di(C₂-C₆)-alkylamino, N—

C₂-C₇-alkylaminocarbonyl, N—

C₂-C₇-cycloalkylaminocarbonyl or C₂-C₄-alkoxycarbonyl,

provided;

if none of the groups A₂ and A₃ is nitrogen, R³ and R⁴, together with the carbon to which they are bonded, can form a 5- or 6-membered ring which comprises 0, 1 or 2 nitrogen atoms and/or 0 or 1 oxygen atom and/or 0 or 1 sulphur atom, or

if none of the groups A₁ and A₂ is nitrogen, R² and R³, together with the carbon to which they are bonded, can form a 6-membered ring which comprises 0, 1 or 2 nitrogen atoms;

U is a group C(═

W), SO or SO₂;

W is oxygen or sulphur;

L is a bivalent chemical group which is —

NHC(═

W)—

, —

NR⁶C(═

W)—

, —

CH₂NHC(═

W)—

, —

CH₂NR⁶C(═

W)—

, —

C(═

W)NH—

, —

C(═

W)NR⁶—

, —

C(═

W)NHCH₂—

, —

C(═

W)NR⁶CH₂—

, —

CH₂NHC(═

W)NH—

, —

CH₂NHC(═

W)NR⁶—

, —

NH(C═

W)NH—

, —

NH(═

W)NR⁶—

, —

NR⁶(C═

W)NH—

, —

NR⁶(═

W)NR⁶—

, —

C(═

W)—

, —

C(═

W)O—

, —

C(═

W)OCH₂C(═

W)—

, —

C(═

W)OCH₂C(═

W)NR⁶—

, —

C(═

W)OCH₂C(═

W)NHC(═

W)NH—

, —

C(═

W)OCH₂C(═

W)NH—

, —

CH₂—

, —

(CH₂)₂—

, —

(CH₂)₃—

, —

Si—

, —

O—

, —

S(O)_p—

, —

CH₂—

S(O)_p—

, —

SO(═

N—

CN)—

—

S(═

N—

CN)—

, or —

C(═

W)NHSO₂—

;

p is 0, 1 or 2;

R⁶ is hydrogen or one of optionally substituted groups C₁-C₆-alkyl, aryl(C₁-C₃)-alkyl, heteroaryl(C₁-C₃)-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₄-C₇-alkylcycloalkyl C₄-C₇-cycloalkylalkyl, C₂-C₇-alkylcarbonyl, or C₂-C₇-alkoxycarbonyl;

m is 0 or 1;

Q is hydrogen or one of optionally substituted groups C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, cyano-C₁-C₂-alkyl, C₁-C₅-heterocycloalkyl, C₁-C₄-alkoxy, C₄-C₇-alkylcycloalkyl, C₄-C₇-cycloalkylalkyl, C₂-C₇-alkylcarbonyl, C₁-C₆-alkylaldehyde, C₁-C₆-hydroxyalkyl, C₂-C₇-alkoxycarbonyl, C₁-C₆-haloalkyl, is formyl, hydroxy, halogen, cyano, aryl(C₁-C₃)-alkyl, heteroaryl(C₁-C₃)-alkyl, OR⁷ or NR⁶R⁸;

R⁷ is one of optionally substituted groups C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₄-C₇-alkylcycloalkyl or C₄-C₇-cycloalkylalkyl;

R⁸ is hydrogen or one of optionally R⁹-substituted groups C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₄-C₇-alkylcycloalkyl or C₄-C₇-cycloalkylalkyl;

R⁹ is hydrogen or one of optionally R¹⁰-substituted groups C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₄-C₇-alkylcycloalkyl or C₄-C₇-cycloalkylalkyl;

R¹⁰ is halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, —

CN, or —

NO₂;

T is a radical (T-1) to (T-90) which may be optionally Z-polysubstituted;

3. The method according to claim 2 wherein

R¹ is hydrogen or one of the optionally substituted groups C₁-C₆-alkyl, C₂-C₆-alkylene, C₂-C₆-alkynyl, C₃-C₇-cycloalkyl, C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl, cyano-C₁-C₂-alkyl, aryl(C₁-C₃)-alkyl, or heteroaryl(C₁-C₃)-alkyl;

A₁ is CR² or nitrogen,

A₂ is CR³ or nitrogen,

A₃ is CR⁴ or nitrogen and

A₄ is CR⁵ or nitrogen, wherein at most three of the chemical groups A₁ to A₄ are nitrogen at the same time, and wherein

R², R³, R⁴ and R⁵, independently of one another, are

hydrogen, halogen, CN, NO₂, optionally substituted C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-haloalkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₆-haloalkylsulphonyl, N—

C₂-C₇-alkylaminocarbonyl, or N—

C₂-C₇-cycloalkylaminocarbonyl,

provided;

if none of the groups A₂ and A₃ is nitrogen, then R³ and R⁴, together with the carbon to which they are bonded attached, can form a 5- or 6-membered ring which comprises 0;

1 or 2 nitrogen atoms and/or 0 or 1 oxygen atom and/or 0 or 1 sulphur atom, or

if none of the groups A₁ and A₂ is nitrogen, then R² and R³, together with the carbon to which they are bonded, can form a 6-membered ring which comprises 0, 1 or 2 nitrogen atoms;

U is a group C(═

W), SO or SO₂;

W is oxygen or sulphur;

L is a bivalent chemical group which is —

CH₂NHC(═

W)—

, —

CH₂NR⁶C(═

W)—

, —

C(═

W)NH, —

C(═

W)NR⁶—

, —

NH(C═

W)NH—

, —

NH(C═

W)NR⁶—

, —

NR⁶(C═

W)NH—

, —

NR⁶(═

W)NR⁶—

, —

C(═

W)—

, —

C(═

W)O—

, —

C(═

W)OCH₂C(═

W)—

, —

C(═

W)OCH₂C(═

W)NR⁶—

, —

C(═

W)OCH₂C(═

W)NHC(═

W)NH—

, —

C(═

W)OCH₂C(═

W)NH—

, —

O—

, —

S(O)_p, and —

CH₂—

S(O)_p—

, —

SO(═

N—

CN)—

S(═

N—

CN)—

, or —

C(═

W)NHSO₂—

,

p is 0, 1 or 2 and

R⁶ is hydrogen, C₁-C₆-alkyl, aryl(C₁-C₃)-alkyl, heteroaryl(C₁-C₃)-alkyl, C₂-C₇-alkylcarbonyl, or C₂-C₇-alkoxycarbonyl;

m is 0 or 1;

Q is hydrogen or one of optionally substituted groups C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, cyano-C₁-C₂-alkyl, C₁-C₅-heterocycloalkyl, C₁-C₄-alkoxy, C₄-C₇-alkylcycloalkyl, C₄-C₇-cycloalkylalkyl, C₂-C₇-alkylcarbonyl, C₁-C₆-alkylaldehyde, C₁-C₆-hydroxyalkyl, C₂-C₇-alkoxycarbonyl, C₁-C₆-haloalkyl, cyano, aryl(C₁-C₃)-alkyl, or heteroaryl(C₁-C₃)-alkyl, or is a group NR⁶R⁸, where

R⁸ is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₄-C₇-alkylcycloalkyl or C₄-C₇-cycloalkylalkyl;

T is one of optionally Z-mono- or -polysubstituted heterocycles (T-5), (T-7), (T-9), (T-10), (T-12), (T-13), (T-15), (T-16), (T-19), (T-20), (T-23), (T-26), (T-28), (T-29), (T-34), (T-35), (T-36), (T-30), (T-33), (T-37), (T-46), (T-51), (T-52), or (T-53), where

n is 0, 1, 2, 3 or 4 and

Z is hydrogen, chlorine, bromine, iodine, cyano, nitro or one of optionally substituted groups C₁-C₄-alkyl, C₁-C₄-alkenyl, C₁-C₄-alkynyl, C₁-C₄-haloalkyl, C₃-C₆-Cycloalkyl, C₃-C₆-halocycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulphinyl, C₁-C₄-haloalkylsulphinyl, C₁-C₄-alkylsulphonyl, C₁-C₄-haloalkylsulphonyl, or N,N-di(C₁-C₄)-alkylamino, or is optionally R¹⁸-substituted phenyl or optionally R¹⁸-substituted pyridinyl;

R¹⁸ is halogen, —

OH, —

NH₂, —

COOH, —

CN, —

NO₂, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulphinyl, C₁-C₄-haloalkylsulphinyl, C₁-C₄-alkylsulphonyl, C₁-C₄-haloalkylsulphonyl, C₁-C₄-alkylamino, N,N-di(C₁-C₄)-alkylamino, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylaminocarbonyl or N,N-di(C₁-C₄)-alkylaminocarbonyl;

or

L, Q and R⁴, together with the carbon atoms to which they are bonded, form an optionally substituted 5- or 6-membered ring which optionally comprises 0, 1 or 2 nitrogen atoms and/or 0 or 1 oxygen atom and/or 0 or 1 sulphur atom.

4. The method according to claim 3 wherein

R¹ is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butynyl, isobutyl, sec-butyl, tert-butyl, methoxymethyl, ethoxymethyl, propoxymethyl, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, allyl, propargyl, isopropylcarbonyl, sec-butylcarbonyl, tert-butylcarbonyl, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, cyanomethyl, or 2-cyanoethyl;

A₁ is CR² or nitrogen,

A₂ is CR³ or nitrogen,

A₃ is CR⁴ or nitrogen and

A₄ is CR⁵ or nitrogen, wherein at most three of the chemical groups A₁ to A₄ are nitrogen at the same time, and where

R² and R⁵, independently of one another, are hydrogen, methyl, fluorine and chlorine and

R³ and R⁴, independently of one another, are hydrogen, fluorine, chlorine, bromine, CN, NO₂, methyl, ethyl, fluoromethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, methoxy, ethoxy, n-propoxy, 1-methylethoxy, fluoromethoxy, difluoromethoxy, chlorodifluoromethoxy, dichlorofluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2,2-difluoroethoxy, pentafluoroethoxy, methylsulphonyl, methylsulphinyl, trifluoromethylsulphonyl, trifluoromethylsulphinyl or N-cyclopropylaminocarbonyl;

U is C(═

W),

W is oxygen,

L is a bivalent chemical group which is —

C(═

O)NH, —

C(═

O)NR⁶, —

C(═

O)O—

, —

C(═

O)OCH₂C(═

O)—

, —

C(═

O)OCH₂C(═

O)NR⁶—

, —

C(═

O)OCH₂C(═

O)NHC(═

O)NH—

, —

C(═

O)OCH₂C(═

O)NH—

, or —

C(═

W)NHSO₂—

, where

R⁶ is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, methoxymethyl, ethoxymethyl, propoxymethyl, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, sec-butylcarbonyl, tert-butylcarbonyl, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, cyanomethyl, or 2-cyanoethyl;

m is 1;

Q is hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, 1,1-dimethylethyl, 1-methylpropyl, 2-methylpropyl, 2-methylbutyl, hydroxymethyl, 2-hydroxypropyl, cyanomethyl, 2-cyanoethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1-trifluoromethylethyl, 2,2-difluoropropyl, 2,2-dimethyl-3-fluoropropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-cyclopropylethyl, bis(cyclopropyl)methyl, 2,2-dimethylcyclopropylmethyl, 2-phenylcyclopropyl, 2,2-dichlorocyclopropyl, trans-2-chlorocyclopropyl, cis-2-chlorocyclopropyl, 2,2-difluorocyclopropyl, trans-2-fluorocyclopropyl, cis-2-fluorocyclopropyl, trans-4-hydroxycyclohexyl, 4-trifluoromethylcyclohexyl, prop-2-enyl, 2-methylprop-2-enyl, prop-2-ynyl, 1,1-dimethylbut-2-ynyl, 3-chloroprop-2-enyl, 3,3-dichloroprop-2-enyl, 3,3-dichloro-1,1-dimethylprop-2-enyl, oxetan-3-yl, isoxazol-3-ylmethyl, 1,2,4-triazol-3-ylmethyl, 3-methyloxetan-3-ylmethyl, benzyl, 2,6-difluorophenylmethyl, 3-fluorophenylmethyl, 2-fluorophenylmethyl, 2,5-difluorophenylmethyl, 1-phenylethyl, 4-chlorophenylethyl, 2-trifluoromethylphenylethyl, 1-pyridin-2-ylethyl, pyridin-2-ylmethyl, 5-fluoropyridin-2-ylmethyl, pyrimidin-2-ylmethyl, methoxy, 2-ethoxyethyl, 2-(methylsulphanyl)ethyl, 1-methyl-2-(ethylsulphanyl)ethyl, 2-methyl-1-(methylsulphanyl)propan-2-yl, methoxycarbonyl, methoxycarbonylmethyl, NH₂, N-ethylamino, N-allylamino, N,N-dimethylamino, or N,N-diethylamino;

T is one of optionally Z-polysubstituted heterocycles (T-12), (T-13), (T-15), (T-16), (T-19), (T-20), (T-23), (T-26), (T-30), (T-33), (T-37), (T-46), (T-51), (T-52), or (T-53);

where

n is 0, 1, 2 or 3 and

Z is hydrogen, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, ethenyl, 1-propenyl, 2-propenyl, ethynyl, 1-propynyl, 1-butynyl, difluoromethyl, trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trifluoromethyl, chloromethyl, bromomethyl, 1-fluoroethyl, 1-fluoro-1-methylethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,2,2,2-tetrafluoroethyl, 1-chloro-1,2,2,2-tetrafluoroethyl, 2,2,2-trichloroethyl, 2-chloro-2,2-difluoroethyl, 1,1-difluoroethyl, pentafluoroethyl, pentafluoro-tert-butyl, heptafluoro-n-propyl, heptafluoro-isopropyl, nonafluoro-n-butyl, trifluoromethoxy-1,1,2,2-tetrafluoroethoxydifluoromethyl, trifluoromethylthio, trifluoromethylsulphinyl, trifluoromethylsulphonyl, methoxy, ethoxy, n-propoxy, trifluoromethoxy, difluoromethoxy, cyclopropyl, cyclobutyl, 2,2,2-trifluoroethoxy, 1-trifluoromethylethoxy, 3,3,3,2,2-pentafluoropropoxy, 4-fluorophenyl, chlorphenyl, 4-trifluoromethylphenyl, 2,2,2-trifluoroethyl, 2,2-difluoro-1-methylcyclopropyl, phenyl, methoxymethyl, cyclopropyl(fluoro)methyl, 2,4-dichlorophenyl, 4-trifluoromethoxyphenyl, 2-chlorophenyl, 3,5-bis(trifluoromethyl)phenyl, or (1,1,1,3,3-hexafluoropropan-2-yl)oxy

or

L, Q and R⁴, together with the carbon atoms to which they are bonded, form an optionally substituted 5- or 6-membered ring which optionally comprises 0, 1 or 2 nitrogen atoms and/or 0 or 1 oxygen atom and/or 0 or 1 sulphur atom.

5. The method according to claim 2 wherein the compound of formula (I) is a compound of formula (Ia), (Ib), (Ic), (Id), (Ie), (If), (Ig), (Ih), (Ii), (Ij), (Ik), (Il), (Im), (In), (Io), (Ip), (Iq), (Ir), (Is), (It), (Iu) or (Iv):

15. The method according to claim 1 wherein said animal pest is an insect, arachnid, or nematode.

6. A compound of formula (Ia), (Ib), (Ic), (Id), (Ie), (If), (Ig), (Ih), (Ii), (Ij), (Im), (In), (Io), (Ip), (Iq), (Ir), (Is), (It), (Iu), or (Iv):

16. A medicament comprising a compound of formula (Ia), (Ib), (Ic), (Id), (Ie), (If), (Ig), (Ih), (Ii), (Ij), (Im), (In), (Io), (Ip), (Iq), (Ir), (Is), (It), (Iu), or (Iv) according to claim 6.

17. A pharmaceutical composition comprising a compound of formula (Ia), (Ib), (Ic), (Id), (Ie), (If), (Ig), (Ih), (Ii), (Ij), (Im), (In), (Io), (Ip), (Iq), (Ir), (Is), (It), (Iu), or (Iv) as defined in claim 6.

18. A crop protection composition comprising a compound of formula formula (Ia), (Ib), (Ic), (Id), (Ie), (If), (Ig), (Ih), (Ii), (Ij), (Im), (In), (Io), (Ip), (Iq), (Ir), (Is), (It), (Iu), or (Iv) as defined in claim 6, and extenders and/or surface-active substances.

19. A method of controlling a pest comprising allowing a compound of formula (Ia), (Ib), (Ic), (Id), (Ie), (If), (Ig), (Ih), (Ii), (Ij), (Im), (In), (Io), (Ip), (Iq), (Ir), (Is), (It), (Iu), or (Iv) as defined in claim 6, to act on said pest or a habitat thereof.

20. A method of protecting propagation material of plants comprising contacting a compound of formula (Ia), (Ib), (Ic), (Id), (Ie), (If), (Ig), (Ih), (Ii), (Ij), (Im), (In), (Io), (Ip), (Iq), (Ir), (Is), (It), (Iu), or (Iv) as defined in claim 6, with said propagation material.

21. The method according to claim 20 wherein said propagation material is seed material.

22. A process of preparing a crop protection composition comprising mixing the compound of formula (Ia), (Ib), (Ic), (Id), (Ie), (If), (Ig), (Ih), (Ii), (Ij), (Im), (In), (Io), (Ip), (Iq), (Ir), (Is), (It), (It), (Iu), or (Iv) as defined in claim 6, with extenders and/or surface-active substances.

23. A process of preparing a pharmaceutical composition comprising mixing the compound of formula (Ia), (Ib), (Ic), (Id), (Ie), (If), (Ig), (Ih), (Ii), (Ij), (Im), (In), (Io), (Ip), (Iq), (Ir), (Is), (It), (Iu), or (Iv) as defined in claim 6, with a pharmaceutically acceptable excipient and/or auxiliary.

7-10. -10. (canceled)

11. A compound of formula (V-6)

12-14. -14. (canceled)