AU2005311429A1 - Hydrazide compounds for combating animal pests - Google Patents

Hydrazide compounds for combating animal pests Download PDF

Info

Publication number
AU2005311429A1
AU2005311429A1 AU2005311429A AU2005311429A AU2005311429A1 AU 2005311429 A1 AU2005311429 A1 AU 2005311429A1 AU 2005311429 A AU2005311429 A AU 2005311429A AU 2005311429 A AU2005311429 A AU 2005311429A AU 2005311429 A1 AU2005311429 A1 AU 2005311429A1
Authority
AU
Australia
Prior art keywords
clo
alkyl
phenyl
och
alkoxy
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
AU2005311429A
Inventor
Douglas Anspaugh
Deborah L. Culbertson
Michael Hofmann
David G. Kuhn
Michael Rack
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of AU2005311429A1 publication Critical patent/AU2005311429A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
    • C07C243/38—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/42—Hydrazines having nitrogen atoms of hydrazine groups further singly-bound to hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/28—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/12—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings condensed with a carbocyclic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/20—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Description

WO 2006/058730 PCT/EP2005/012787 1 Hydrazide Compounds for Combating Animal Pests The present invention relates to new hydrazide compounds which are useful for combating animal pests, in particular insects, arachnids and nematodes. The invention 5 also relates to a method for combating insects, nematodes and arachnids. In spite of commercial pesticides available today, damage to crops, both growing and harvested, the damage of non-living material, in particular cellulose based materials such as wood or paper, and other nuisance, such as transmission of diseases, caused 10 by animal pests still occur. JP 2000169461 describes inter alia thiadiazolylcarbonylhydrazones of phenylketones having insecticidal or fungicidal activity. However, the insecticidal activity of these compounds is not satisfactory. 15 A. M. Islam et al., Egyptian Jornal of Chemistry 1986, 29(4) S. 405-431 (CASREACT 111:173716) discloses several naphthalin-2-yl sulfonylhydrazones of aromatic aldehydes, which were screened against cotton leaf worm (Spodoptera literalis). However, the activity of these compounds against other pests is not satisfactory. 20 Therefore, there is continuing need to provide compounds which are useful for combating insects, nematodes and arachnids. T.M. Temerk et al. Bull. Soc. Chim. Belg. 89(7), 1980, S. 489-498 describe the 25 polarographic reduction in accordance with the following scheme: O + 2H+ + 2 e- H N N H H International application PCT/EP 2004/005681 discloses compounds of the general 30 formula Ar -(CH 2 )n- Y - NH - N= C /Ra R 3a R2 a , R4a WO 2006/058730 PCT/EP2005/012787 2 wherein Ar is an optionally substituted cyclic radical, selected from phenyl, napthyl and heterocyclic radicals, n is 0 or 1, Y is inter alia CO or SO 2 , R" is H, C 1
-C
1 0 -alkyl, Cl
C
1 0 -haloalkyl, C 3 -Clo-cycloalkyl, C 3 -Co 10 -halocycloalkyl, C 2 -Co 10 -alkenyl, C 2 -Co 10 haloalkenyl, C 2
-C
10 -alkynyl, C 2 -Co 10 -haloalkynyl or optionally substituted phenyl, R 2a and 5 R 3 are inter alia H, C 1
-C
1 0 -alkyl, C 1 -Clo-haloalkyl, halogen, optionally substituted phenyl or cyano and R 4a is inter alia an optionally substituted aromatic radical selected from phenyl, pyridyl, pyrimidyl, furyl and thienyl. These compounds are active against insects and arachnids. 10 It is an object of the present invention to provide further compounds having a good activity against insects, nematodes and/or arachnids and thus are useful for combating said pests. The inventors of the present application surprisingly found that this object is achieved 15 by compounds of formula I as defined below and the salts thereof. These compounds have not yet been described, except for a compound of formula I, wherein A and Ar are unsubstituted phenyl, Q is a single bond, X is C=O and R', R 2 , R 3 , R 5 and R 6 are hydrogen. 20 Therefore, the present invention relates to compounds of the general formula I 6 2/ I Ar (I) Q N 15 1 3 R R R and to the salts thereof, wherein 25 ..... is absent or a covalent bond; A is a cyclic radical selected from phenyl and a 5- or 6-membered heterocyclic radi cal with 1 to 4 heteroatoms as ring members which are selected, independently 30 of one another, from O, N and S, the 5- or 6-membered heterocyclic radical may have a carbonyl group as ring member, and where the cyclic radical may have 1, 2, 3, 4 or 5 substituents Ra which are selected, independently of one another, from halogen, cyano, nitro, C 1 -Co 10 -alkyl, Cl-Co 10 -haloalkyl, C 3
-C
1 0 -cycloalkyl, C 3 C 10 o-halocycloalkyl, C 2 -C, 0 -alkenyl, C 2 -C 10-haloalkenyl, C 2 -C 10-alkynyl, C 3 -Co 35 haloalkynyl, C 1 -Co 1 0 -alkoxy, C 1 -Co 10 -haloalkoxy, C 2 -Co 10 -alkenyloxy, C 2 -Co 10 haloalkenyloxy, C 2 -Co 10 -alkynyloxy, C 3
-C
1 0 -haloalkynyloxy, C 1 -Co 1 0 -alkylthio, Cl- WO 2006/058730 PCT/EP2005/012787 3 Clo 0 -haloalkylthio, C 1 -Co 10 -alkylsulfinyl, C 1 -Clo-haloalkylsulfinyl, Cl-Clo alkylsulfonyl, Cl-Co 10 -haloalkylsulfonyl, hydroxy, NR 7
R
8 , C-Co 10 -alkoxycarbonyl,
C
1 -Clo-haloalkoxycarbonyl,
C
2 -Co 10 -alkenyloxycarbonyl, C2-C0 0 -haloalkenyloxy carbonyl, Cl-Clo-alkylcarbonyl, C-Co 10 -haloalkylcarbonyl, R 7
R
8 N-CO-, phenyl, 5 benzyl and phenoxy, wherein phenyl, benzyl and phenoxy may be substituted by 1, 2, 3, 4 or 5 substituents Rb which are selected, independently of one another, from halogen, cyano, nitro, C 1 -Clo 0 -alkyl, C 1 -Co 10 -haloalkyl, C 3 -Co 10 -cycloalkyl, C3
C
1 0 -halocycloalkyl, C 2 -Co 10 -alkenyl, C 2 -Co 1 0 -haloalkenyl, C 2 -Co 10 -alkynyl, C3-Clo haloalkynyl, C-Co 10 -alkoxy, Cl-Clo-haloalkoxy, C 2 -Co 10 -alkenyloxy, C2-C1o 10 haloalkenyloxy, C 2 -Co 10 -alkynyloxy, C 3 -Co 10 -haloalkynyloxy, C 1 -Co-alkylthio, Cl
C
1 o-haloalkylthio, Cl-Clo-alkylsulfinyl, C-Co-haloalkylsulfinyl, Cl-Cso alkylsulfonyl, Cl-Co 10 -haloalkylsulfonyl, hydroxy, NR 7
R
8 , Cl-Clo-alkoxycarbonyl, Cl-C 0 -haloalkoxycarbonyl, C 2 -Cl-alkenyloxycarbonyl, C2-C1o haloalkenyloxycarbonyl,
C
1 -Co 10 -alkylcarbonyl, C-Co 10 -haloalkylcarbonyl and 15 R 7
R
8 N-CO-, wherein in each case two radicals R a which are bound to adjacent carbon atoms may form a CH=CH-CH=CH moiety or a O-CH 2 -O moiety, where in these two moieties 1 or 2 hydrogen atoms may be replaced by a radical Rb as defined above; 20 Q is selected from the group consisting of a single bond, C01-C4 alkylidene, O-C1-C4 alkylidene, S-C 1
-C
4 alkylidene and NR 9
-C
1
-C
4 alkylidene, wherein the alkylidene group in the last four mentioned radicals is unsubstituted or carries 1, 2, 3 or 4 substituents selected from OH, =0, halogen, C01-C4 haloalkyl and C-C4 alkoxy; 25 or the moiety A-Q may together be CI-C 10 -alkyl, which may be substituted by 1 or 2 substituents selected from the group consisting of =0, OH, C l
-C
4 -alkoxy, C1-C4 alkylthio, halogen or C-C 4 -alkylcarbonyloxy; 30 X is C=O, C=S or SO 2 ; Ar is an aromatic radical selected from phenyl, naphthyl, pyridyl, pyrimidyl, furyl and thienyl, where the aromatic radical may carry 1, 2, 3, 4 or 5 substituents Rc which are selected, independently of one another, from halogen, cyano, nitro, C1-C1o 35 alkyl, Cl-Co-haloalkyl, C3-Clo-cycloalkyl, C3-Co 10 -halocycloalkyl, C 2 -Co 10 -alkenyl,
C
2 -Co 1 0 -haloalkenyl, C2-Co 10 -alkynyl, C3-Co 10 -haloalkynyl, Cl-C 1 o-alkoxy, C1-Co0 haloalkoxy, C2-Co 10 -alkenyloxy, C 2 -Co 10 -alkynyloxy, C 3 -Co 10 -haloalkynyloxy, C1-Co0 alkylthio, Cl-C 10 -haloalkylthio, C 1 -Clo-alkylsulfinyl, C-Co 0 -haloalkylsulfinyl, C-Co0 alkylsulfonyl, C-Co 10 -haloalkylsulfonyl, hydroxy, NR 7
R
8 , C-Co 10 -alkoxycarbonyl, 40 Cl-Clo-haloalkoxycarbonyl, C2-Co 10 -alkenyloxycarbonyl,
C
2 -Co 10 -haloalkenyloxy- WO 2006/058730 PCT/EP2005/012787 4 carbonyl, Cl-Clo-alkylcarbonyl, Cl-C 1 0 -haloalkylcarbonyl, C 1 -Co 10 -alkylcarbonyloxy,
R
7
R
8 N-CO-, phenyl, benzyl and phenoxy, wherein phenyl, benzyl and phenoxy may be unsubstituted or substituted by 1, 2, 3, 4 or 5 substituents Rb as defined above and wherein two radicals Rc which are bound to adjacent carbon atoms 5 may form a O-CH 2 -O moiety, where in said moiety 1 or 2 hydrogen atoms may be replaced by a radical Rb as defined above; R' is selected from the group consisiting of H, Cl-Clo-alkyl, C 1 -Co 10 -haloalkyl, C 3 -Co 10 cycloalkyl, C 3 -Co 10 -halocycloalkyl, C 2 -Co 10 -alkenyl, C 2 -Co 10 -haloalkenyl, C 2 -Co 10 alkynyl, C 2 -Co 10 -haloalkynyl, phenyl and a 5- or 6-membered heterocyclic radical with 1 to 4 heteroatoms which are selected, independently of one another, from O, N and S, it being possible for the aforementioned two last radicals to be unsubstituted or substituted by 1, 2, 3, 4 or 5 substituents R a as defined above; 15 R 2 is a monovalent radical selected from H, halogen, cyano, Cl-C 1 o-alkyl, C 1 -Co 10 haloalkyl, C 3 -Cl 1 -cycloalkyl, C 3 -Co 10 -halocycloalkyl, C 2 -Co 10 -alkenyl, C2-Cio haloalkenyl, C 2 -Co 10 -alkynyl, C 3 -Co 10 -haloalkynyl, C 1 -Co 10 -alkoxy, C 1 -Co 10 -haloalkoxy,
C
2 -Co 10 -alkenyloxy, C 2 -Co 10 -haloalkenyloxy, C 2 -Co 10 -alkynyloxy, C 3 -Co 1 0 haloalkynyloxy, Cl-Co 10 -alkylthio, Cl-Clo-haloalkylthio, hydroxy-C 1 -Co 0 -alkyl, C 1 20 C 10 -alkoxy-Cl-Co 0 -alkyl, halo-C 1 -Co 10 -alkoxy-C 1
-C
1 0 -alkyl, Cl-Co 10 -alkoxycarbonyl
C
1 -Co 10 -alkyl, halo-C 1 -Co 10 -alkoxycarbonyl-C l -Clo-alkyl and phenyl which may be substituted by 1, 2, 3, 4 or 5 substituents Rb as defined above;
R
3 is selected from the group consisiting of H, halogen, cyano, C 1 -Cl 0 -alkyl, C 1 -Co 10 25 haloalkyl, C 3 -Co 1 0 -cycloalkyl, C 3 -Co 10 -halocycloalkyl, C 2 -C 0 -alkenyl, C2-Co10 haloalkenyl, C 2 -Co 10 -alkynyl, C 3 -Co 10 -haloalkynyl, Cl-Co 10 -alkoxy, C 1 -Co 10 -haloalkoxy,
C
2 -Co 10 -alkenyloxy, C 2 -Co 10 -haloalkenyloxy, C 2 -Co 10 -alkynyloxy, C3-C1o haloalkynyloxy, Cl-Co 10 -alkylthio, C 1 -Co 10 -haloalkylthio, hydroxy-C 1 -Co 10 -alkyl, C 1 C 10 o-alkoxy- Cl-Clo-alkyl, halo-C 1 -Co 0 -alkoxy-Cl-Co 10 -alkyl, Cl-Co 10 -alkoxycarbonyl 30 C 1 -Co 10 -alkyl, halo-Cl-C 1 o-alkoxycarbonyl-C l -Clo-alkyl and phenyl which may be substituted by 1, 2, 3, 4 or 5 substituents Rb as defined above;
R
4 is hydrogen or has one of the meanings given for Rc or 35 R 4 together with R 2 is a bivalent radical Y, which is selected from O, S, CR 1 o=N, N=N, O-CR"R 1 2 , S-CR"R 12, N(R 13
)-CR"RR
12 , O-C(0), O-C(S), S-C(0); N(R 13 )-C(0) or N(R 3)-C(S);
R
5 is selected from the group consisiting of H, C 1 -Co 10 -alkyl, C 1 -Clo-haloalkyl, C 3 -Co 10 40 cycloalkyl, C 3
-C
1 0 -halocycloalkyl, C 2 -Co 10 -alkenyl, C 2 -Co 10 -haloalkenyl, C 2 -Co 10
-
WO 2006/058730 PCT/EP2005/012787 5 alkynyl, C 2 -Co 10 -haloalkynyl, benzyl and phenyl wherein benzyl and phenyl may be substituted by 1, 2, 3, 4 or 5 substituents Rd which are selected, independently of one another, from halogen, cyano, nitro, C 1 -Co 10 -alkyl, C 1 -Co 10 -haloalkyl, C3-Co0 cycloalkyl, C 3 -Co 10 -halocycloalkyl, C 2 -Co 10 -alkenyl, C2-C1 0 -haloalkenyl, C2-Co10 5 alkynyl, C 3
-C
1 0 -haloalkynyl, C 1 -Co 1 0 -alkoxy, Cl-Co 10 -haloalkoxy, C 2 -Co 10 -alkenyloxy, C2-Co 1 0 -haloalkenyloxy, C2-Clo -alkynyloxy, C3-Clo 0 -haloalkynyloxy, C1-Co 10 -alkylthio,
C
1 -Co 10 -haloalkylthio, C 1 -Clo-alkylsulfinyl, Cl-Co 10 -haloalkylsulfinyl, CI-Clo alkylsulfonyl, Cl-Cl 0 -haloalkylsulfonyl, hydroxy, NR 7
R
8 , Cl-Co-alkoxycarbonyl, Cl-Clo-haloalkoxycarbonyl, C 2 -Co 10 -alkenyloxycarbonyl, C2-Clo 10 haloalkenyloxycarbonyl, C 1 -Co 10 -alkylcarbonyl, Cl-Co 10 -haloalkylcarbonyl and R 7 RN-CO-;
R
6 is selected from the group consisiting of H, Cl-Clo-alkyl optionally substituted by CN or NO 2 , C 1 -Co 10 -haloalkyl, C 3 -Co 10 -cycloalkyl, C 3 -Co 10 -halocycloalkyl, C2-Clo 15 alkenyl, C 2 -Co 10 -haloalkenyl, C2-Co 10 -alkynyl, C 2 -Co 10 -haloalkynyl, C 1 -CIo-alkylthio,
C
1 -Co 10 -haloalkylthio, C 1 -Clo-alkylsulfinyl, C-Co 10 -haloalkylsulfinyl, Cj-C1o alkylsulfonyl, Cl-Co 10 -haloalkylsulfonyl, Cl-Cl 0 -alkoxycarbonyl, Cj-Cjo haloalkoxycarbonyl, C2-Clo -alkenyloxycarbonyl, C2-Clo -haloalkenyloxycarbonyl,
C
1 -Co 10 -alkylcarbonyl, where the alkyl moiety of alkylcarbonyl may be 20 unsubstituted or substituted by 1, 2 or 3 substituents selected from the group consisting of Cl-Co 10 -alkylthio, phenylthio, phenyl and phenoxy, Cj-Co 10 haloalkylcarbonyl, C2-Clo -alkenylcarbonyl, hydroxy-Cl-C 0 -alkyl, C1-C 0 -alkoxy
C
1 -Co 10 -alkyl, halo-C 1 -Co 0 -alkoxy-C-Co 0 -alkyl, Cl-Co 10 -alkoxycarbonyl-C 1 -Co 0 -alkyl, halo-C 1 -Co 0 -alkoxycarbonyl-C l -Clo-alkyl, R 7
R
8 N-CO-, benzoyl (C 6
H
5 -CO-), C3 25 Co 10 -cycloalkylcarbonyl, R 6 a-CO-, wherein R 6 a is C 1
-C
4 -alkoxycarbonyl, phenoxy, naphthyl or a 5- or 6-membered heterocyclic radical with 1 to 4 heteroatoms which are selected, independently of one another, from O, N and S, it being possible for phenoxy, naphthyl and the 5- or 6-membered heterocyclic radical to be unsubstituted or substituted by 1, 2, 3, 4 or 5 substituents R a as defined 30 above, and benzyl wherein benzyl may be substituted by 1, 2, 3, 4 or 5 substituents Rb as defined above; R 7 , R 8 are selected independently of one another from H, C-Co 10 -alkyl, C 1 -Co 10 -haloalkyl,
C
3
-C
10 -cycloalkyl, C 3 -Co 10 -halocycloalkyl, C2-Co 10 -alkenyl, C 2 -Co 10 -haloalkenyl, C2 35 Co 10 -alkynyl, C 3 -Clo-haloalkynyl, phenyl, benzoyl, naphthyl or benzyl wherein the phenyl ring in the aforementioned four radicals may be substituted by 1, 2, 3, 4 or 5 substituents which are selected, independently of one another, from halogen, cyano, nitro, C 1 -Co 10 -alkyl, Cl-C 0 lo-haloalkyl, C 3 -Co 10 -cycloalkyl, C3-C1o halocycloalkyl, C 2 -Co 10 -alkenyl, C 2 -Co 10 -haloalkenyl, C-Co 10 -alkoxy, Cl-Co 40 haloalkoxy, C-Co 10 -alkylthio, C,-C 1 o-haloalkylthio, C 1 -Co 10 -alkylsulfonyl, C-Co0- WO 2006/058730 PCT/EP2005/012787 6 haloalkylsulfonyl, hydroxy, C 1 -Co 10 -alkoxycarbonyl, Cl-Co 10 -haloalkoxycarbonyl, C2
C
10 o-alkenyloxycarbonyl, C2-C1 0 -haloalkenyloxycarbonyl, Cl-Co 10 -alkylcarbonyl and
C
1 -Co 10 -haloalkylcarbonyl; 5 R 9 is hydrogen, cyano, Cl-Co 10 -alkyl, C 1 -Co 10 -haloalkyl, C 3 -Clo 10 -cycloalkyl, C3-C1o halocycloalkyl, C 2 -Co 10 -alkenyl, C 2 -Co 10 -haloalkenyl, C 2 -Co 10 -alkynyl, C3-C1o haloalkynyl, C 1 -Co 10 -haloalkylsulfonyl, Cl-Clo-alkylcarbonyl, Cj-Cjo haloalkylcarbonyl, R 7
R
8 N-CO-, phenyl or benzyl, wherein phenyl and benzyl may be substituted by 1, 2, 3, 4 or 5 substituents Rb; and 10
R
1 0 is hydrogen or has one of the meanings given for Rc;
R
1 ", R 12 are selected independently of one another from H, C 1 -Co 10 -alkyl, Cj-Cro haloalkyl, C 3 -Co 10 -cycloalkyl, C 3
-C
1 0 -halocycloalkyl, C 2 -Co 10 -alkenyl, C2-C1o 15 haloalkenyl, C 2 -Co 10 -alkynyl and C 3
-C
1 0 -haloalkynyl, C 1 -Co 10 -alkoxy, C,-Clo haloalkoxy, C 1 -Co 10 -alkylthio, C 1
-C
1 0 -haloalkylthio, hydroxy-C 1 -Co 0 -alkyl, Cj-Clo alkoxy-C 1
-C,
0 -alkyl, halo-C-C 10 -alkoxy-C 1 -Co 10 -alkyl, C 1 -Co 10 -alkoxycarbonyl-C 1 C 1 0 o-alkyl, halo-Cl-Co 10 -alkoxycarbonyl-C l -Clo-alkyl, one of the radicals R" 1 or R12 may also be Cl-Co-alkylsulfonyl, C 1 -Co 10 -haloalkylsulfonyl, C 1 -Co 10 -alkoxycarbonyl, 20 Cs-Co 10 -haloalkoxycarbonyl, C 2 -Co 10 -alkenyloxycarbonyl, C2-C10 haloalkenyloxycarbonyl, Cl-Co 10 -alkylcarbonyl, Cl-Co 10 -haloalkylcarbonyl or
R
7
R
8 N-CO-.
R
13 is hydrogen, cyano, Cl-Co 10 -alkyl, Cl-Co 10 -haloalkyl, C 3
-CI
10 -cycloalkyl, C 3 -Co 1 0 25 halocycloalkyl, C 2 -Co 10 -alkenyl, C 2 -Co 10 -haloalkenyl, C 2 -Co 10 -alkynyl, C 3 -Cro haloalkynyl, C 1 -Co 10 -haloalkylsulfonyl, C 1 -Co-alkylcarbonyl, C 1 -Co 10 haloalkylcarbonyl, R 7
R
8 N-CO-, phenyl or benzyl, wherein phenyl and benzyl may be substituted by 1, 2, 3, 4 or 5 substituents Rb; 30 except for a compound of formula I, wherein A and Ar are unsubstituted phenyl, Q is a single bond, X is C=O and R', R 2 , R 3 , R 5 and R 6 are hydrogen. Due to their excellent activity, the compounds of the general formula I can be used for controlling pests, selected from harmful insects, arachnids and nematodes. The 35 compounds of the formula I are in particular useful from combating insects. Accordingly, the invention further provides compositions for combating such pests, preferably in the form of directly sprayable solutions, emulsions, pastes, oil dispersions, powders, materials for scattering, dusts or in the form of granules, which comprises a 40 pesticidally effective amount of at least one compound of the general formula I or at WO 2006/058730 PCT/EP2005/012787 7 least a salt thereof and at least one carrier which may be liquid and/or solid and which is prefarably agronomically acceptable, and/or at least one surfactant. Furthermore, the invention provides a method for combating such pests, which 5 comprises contacting said pests, their habitat, breeding ground, food supply, plant, seed, soil, area, material or environment in which the animal pests are growing or may grow, or the materials, plants, seeds, soils, surfaces or spaces to be protected from an attack of or infestation by said pest, with a pesticidally effective amount of a compound of the general formula I as defined herein or a salt thereof. 10 The invention provides in particular a method for protecting crops, including seeds, from attack or infestation by harmful insects, arachnids and/or nematodes, said method comprises contacting a crop with a pesticidally effective amount of at least one compound of formula I as defined herein or with a salt thereof. 15 The invention also provides a method for protecting non-living materials from attack or infestation by the aforementioned pests, which method comprises contacting the non living material with a pesticidally effective amount of at least one compound of formula I as defined herein or with a salt thereof. 20 Suitable compounds of the general formula I encompass all possible stereoisomers (cis/trans isomers, enantiomers) which may occur and mixtures thereof. Stereoisomeric centers are e.g. the carbon atom of the C(R 2
)=C(R
3 ) group and the C(R 1 ) moiety. The present invention provides both the pure enantiomes or diastereomers or mixtures 25 thereof, the pure cis- and trans-isomers and the mixtures thereof. The compounds of the general formula I may also exist in the form of different tautomers if A or Ar carry amino or hydroxy groups. The invention comprises the single tautomers, if seperable, as well as the tautomer mixtures. 30 Salts of the compounds of the formula I are preferably agriculturally acceptable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid of the anion in question if the compound of formula I has a basic functionality or by reacting an acidic compound of formula I with a suitable base. 35 Suitable agriculturally useful salts are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not have any adverse effect on the action of the compounds according to the present invention. Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and 40 barium, and of the transition metals, preferably manganese, copper, zinc and iron, and WO 2006/058730 PCT/EP2005/012787 8 also ammonium (NH 4 ') and substituted ammonium in which one to four of the hydrogen atoms are replaced by C 1
-C
4 -alkyl, C 1
-C
4 -hydroxyalkyl, C 1
-C
4 -alkoxy, Cl-C 4 -alkoxy-C 1 C 4 -alkyl, hydroxy-C 1 l-C 4 -alkoxy-Cl-C 4 -alkyl, phenyl or benzyl. Examples of substituted ammonium ions comprise methylammonium, isopropylammonium, dimethylammonium, 5 diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2 hydroxyethoxy)ethylammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzyltriethylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C 1
-C
4 -alkyl)sulfonium, and sulfoxonium ions, 10 preferably tri(C-C 4 -alkyl)sulfoxonium. Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, 15 and the anions of C 1
-C
4 -alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting the compounds of the formula I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid. 20 The organic moieties mentioned in the above definitions of the variables are - like the term halogen - collective terms for individual listings of the individual group members. The prefix Cn-Cm indicates in each case the possible number of carbon atoms in the group. 25 "Halogen" or "halo" will be taken to mean fluoro, chloro, bromo and iodo. The term C 1
-C
4 -alkylidene refers to a linear or branched alkanediyl group having 1 to 4 carbon atoms such as methylene (= CH 2 ), 1,2-ethandiyl (= CH 2
CH
2 ), 1,1-ethandiyl (=
CH(CH
3 )), 1,2-propandiyl, 1,3-propandiyl, 2,2-propandiyl, 1,4-butandiyl and the like. 30 According to the invention C 1
-C
4 -alkanediyl is unsubstituted or may carry 1, 2, 3 or 4 substituents selected from OH, =0, halogen C-C4 haloalkyl and C 1
-C
4 alkoxy. The substituent =0 denotes a carbonyl group. The terms "O-C 1
-C
4 -alkylidene" and "S-C0 1
-C
4 -alkylidene", respectively refer to a linear 35 or branched alkanediyl group having 1 to 4 carbon atoms, where one valency is attached to the skeleton via an oxygen or sulfur atom, respectively. The term "Cl-C 1 0 -alkyl" as used herein (and also in C-C 0 lo-alkylsulfinyl and Cl-C10 alkylsulfonyl) refers to a branched or unbranched saturated hydrocarbon group having 40 1 to 10 carbon atoms, for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1- WO 2006/058730 PCT/EP2005/012787 9 methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3 methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 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, 5 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1 -methylpropyl, 1-ethyl-2-methylpropyl, heptyl, octyl, 2-ethylhexyl, nonyl and decyl and their isomers. C 1
-C
4 -alkyl means for example methyl, ethyl, propyl, 1 methylethyl, butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl. 10 The term "Cl-C 10 -haloalkyl" as used herein (and also in Cl-C 0 lo-haloalkylsulfinyl and Cj
C
10 o-haloalkylsulfonyl) refers to a straight-chain or branched alkyl group having 1 to 10 carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, for example CI-C 4 haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, 15 fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2 difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2 dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl and the like. The term Cj
C
1 0 -haloalkyl in particular comprises C 1
-C
2 -fluoroalkyl, which is synonym with methyl or 20 ethyl, wherein 1, 2, 3, 4 or 5 hydrogen atoms are substituted by fluorine atoms, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2 difluoroethyl, 2,2,2-trifluoroethyl and pentafluoromethyl. Similarly, "C 1 -Clo-alkoxy" and "C 1 -Cl 0 -alkylthio" refer to straight-chain or branched alkyl 25 groups having 1 to 10 carbon atoms (as mentioned above) bonded through oxygen or sulfur linkages, respectively, in any position in the alkyl group. Examples include Cl-C 4 alkoxy such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy and tert-butoxy, further C 1
-C
4 -alkylthio such as methylthio, ethylthio, propylthio, isopropylthio, and n-butylthio. 30 Accordingly, the terms "C 1
-C
1 0 -haloalkoxy" and " C-C 1 0 -haloalkylthio" refer to straight chain or branched alkyl groups having 1 to 10 carbon atoms (as mentioned above) bonded through oxygen or sulfur linkages, respectively, in any position in the alkyl group, where some or all of the hydrogen atoms in these groups may be replaced by 35 halogen atoms as mentioned above, for example C 1
-C
2 -haloalkoxy, such as chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2 40 difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy and WO 2006/058730 PCT/EP2005/012787 10 pentafluoroethoxy, further Cl-C 2 -haloalkylthio, such as chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1-chloroethylthio, 1-bromoethylthio, 1-fluoroethylthio, 2 5 fluoroethylthio, 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 and pentafluoroethylthio and the like. Similarly the terms C 1
-C
2 -fluoroalkoxy and C 1
-C
2 fluoroalkylthio refer to C 1
-C
2 -fluoroalkyl which is bound to the remainder of the molecule via an oxygen atom or a sulfur atom, respectively. 10 The term "C 2
-C
10 -alkenyl" as used herein intends a branched or unbranched unsaturated hydrocarbon group having 2 to 10 carbon atoms and a double bond in any position, such as ethenyl, 1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2 butenyl, 3-butenyl, 1-methyl-l-propenyl, 2-methyl-l-propenyl, 1-methyl-2-propenyl, 2 15 methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-l-butenyl, 2-methyl-l-butenyl, 3-methyl-l-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-l-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 20 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-l-butenyl, 1,2-dimethyl-2 25 butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-l-butenyl, 1,3-dimethyl-2-butenyl, 1,3 dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-l-butenyl, 2,3-dimethyl-2 butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-l-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 30 methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl. The term "C 2 -Co 10 -haloalkenyl" as used herein intends a branched or unbranched unsaturated hydrocarbon group having 2 to 10 carbon atoms and a double bond in any position, where some or all of the hydrogen atoms in these groups may be replaced by 35 halogen atoms as mentioned above. Similarly, the term "C 2 -Co 10 -alkenyloxy" as used herein intends a branched or unbranched unsaturated hydrocarbon group having 2 to 10 carbon atoms and a double bond in any position, the alkenyl group being bonded through oxygen linkage, in any 40 position in the alkenyl group, for example ethenyloxy, propenyloxy and the like.
WO 2006/058730 PCT/EP2005/012787 11 Accordingly, the term "C 2
-C
1 0 -haloalkenyloxy" as used herein intends a branched or unbranched unsaturated hydrocarbon group having 2 to 10 carbon atoms and a double bond in any position, the alkenyl group being bonded through oxygen linkage,, in any 5 position in the alkenyl group, where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above. The term "C 2
-C
1 0 -alkynyl" as used herein refers to a branched or unbranched unsaturated hydrocarbon group having 2 to 10 carbon atoms and containing at least 10 one triple bond, such as ethynyl, propynyl, 1-butynyl, 2-butynyl, and the like. The term "C 3 -Co 10 -haloalkynyl" as used herein refers to a branched or unbranched unsaturated hydrocarbon group having 3 to 10 carbon atoms and containing at least one triple bond, where some or all of the hydrogen atoms in these groups may be 15 replaced by halogen atoms as mentioned above, with the proviso that the halogen atom is not directly bound to the triple bond. The term "C 2
-C
10 -alkynyloxy" as used herein refers to a branched or unbranched unsaturated hydrocarbon group having 2 to 10 carbon atoms and containing at least 20 one triple bond, the alkynyl group being bonded through oxygen linkage in any position in the alkynyl group. Similarly, the term "C 3
-C
1 0 -haloalkynyloxy" as used herein refers to a branched or unbranched unsaturated hydrocarbon group having 3 to 10 carbon atoms and 25 containing at least one triple bond, the group being bonded through oxygen linkages in any position in the alkynyl group, where some or all of the hydrogen atoms in these group may be replaced by halogen atoms as mentioned above, with the proviso that the halogen atom is not directly bound to the triple bond. 30 The term "C 3 -Co 10 -cycloalkyl" as used herein refers to a monocyclic 3- to 10-membered saturated carbon atom ring, e.g. cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and cyclodecyl. The term "C 3 -Co 10 -halocycloalkyl" as used herein refers to a monocyclic 3- to 10 35 membered saturated carbon atom ring, e.g. cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and cyclodecyl, where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, for example chloro-, dichloro- and trichlorocyclopropyl, fluoro-, difluoro- and trifluorocyclopropyl, chloro-, dichloro-, trichloro, tetrachloro-, pentachloro- and 40 hexachlorocyclohexyl and the like.
WO 2006/058730 PCT/EP2005/012787 12 The term "Cl-Clo-alkylcarbonyl" as used herein refers to C 1
-C
1 0 -alkyl which is bound to the remainder of the molecule via a carbonyl group. Examples include
CO-CH
3 , CO-C 2
H
5 , CO-CH 2
-C
2
H
5 , CO-CH(CH 3
)
2 , n-butylcarbonyl, 5 CO-CH(CH 3
)-C
2
H
5 , CO-CH 2
-CH(CH
3
)
2 , CO-C(CH 3
)
3 , n-pentylcarbonyl, 1 methylbutylcarbonyl, 2-methylbutylcarbonyl, 3-methylbutylcarbonyl, 2,2 dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, n-hexylcarbonyl, 1,1 dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl, 1-methylpentylcarbonyl, 2 methylpentylcarbonyl, 3-methylpentylcarbonyl, 4-methylpentylcarbonyl, 1,1 10 dimethylbutylcarbonyl, 1,2-dimethylbutylcarbonyl, 1,3-dimethylbutylcarbonyl, 2,2 dimethylbutylcarbonyl, 2,3-dimethylbutylcarbonyl, 3,3-dimethylbutylcarbonyl, 1 ethylbutylcarbonyl, 2-ethylbutylcarbonyl, 1,1,2-trimethylpropylcarbonyl, 1,2,2 trimethylpropylcarbonyl, 1-ethyl-1 -methylpropylcarbonyl or 1-ethyl-2 methylpropylcarbonyl. 15 The term "C 1
-C
0 lo-alkoxycarbonyl" as used herein refers to C-C 10 -alkoxy which is bound to the remainder of the molecule via a carbonyl group. Examples include
CO-OCH
3 , CO-OC 2
H
5 , CO-OCH 2
-C
2
H
5 , CO-OCH(CH 3
)
2 , n-butoxycarbonyl,
CO-OCH(CH
3
)-C
2
H
5 , CO-OCH 2
-CH(CH
3
)
2 , CO-OC(CH 3
)
3 , n-pentoxycarbonyl, 1 20 methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2,2 dimethylpropoxycarbonyl, 1I-ethylpropoxycarbonyl, n-hexoxycarbonyl, 1,1 dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2 methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1,1 dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl, 1,3-dimethylbutoxycarbonyl, 2,2 25 dimethylbutoxycarbonyl, 2,3-dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl, 1 ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl, 1,1,2-trimethylpropoxycarbonyl, 1,2,2 trimethylpropoxycarbonyl, 1-ethyl-1-methylpropoxycarbonyl or 1-ethyl-2 methylpropoxycarbonyl. 30 The term "halo-C-Co 10 -alkoxycarbonyl" as used herein refers to C 1 -Co 10 -haloalkoxy which is bound to the remainder of the molecule via a carbonyl group. The terms "hydroxy-Cl-Co 1 0 -alkyl", "Cs-C10-alkoxy-C 1 -Cl 0 -alkyl", "halo-C 1
-C
10 -alkoxy-C 1 Cl 0 -alkyl", "C 1
-C
10 -alkoxycarbonyl-Cl-C 0 -alkyl", "halo-C 1 -Co 10 -alkoxycarbonyl-C-Clo 35 alkyl" as used herein, refer to C 1
-C
10 -alkyl, as defined herein, in particular to methyl, ethyl, 1-propyl or 2-propyl, which is substituted by one radical selected from hydroxy, Cl-Cl 0 -alkoxy, C1-Clo- haloalkoxy, C 1 -Co 10 -alkoxycarbonyl or Cl-C 1 0 -haloalkoxycarbonyl. The term "5- or 6-membered heterocyclic radical with 1, 2, 3 or 4 heteroatoms which 40 are selected, independently of one another, from O, N and S" comprises monocyclic 5- WO 2006/058730 PCT/EP2005/012787 13 or 6-membered heteroaromatic rings and nonaromatic saturated or partially unsaturated 5- or 6-membered mono-heterocycles, which carry 1, 2, 3, or 4 heteroatoms as ring members. The heterocyclic radical may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member. 5 Examples for non-aromatic rings include pyrrolidinyl, pyrazolinyl, imidazolinyl, pyrrolinyl, pyrazolinyl, imidazolinyl, tetrahydrofuranyl, dihydrofuranyl, 1,3-dioxolanyl, dioxolenyl, thiolanyl, dihydrothienyl, oxazolidinyl, isoxazolidinyl, oxazolinyl, isoxazolinyl, thiazolinyl, isothiazolinyl, thiazolidinyl, isothiazolidinyl, oxathiolanyl, piperidinyl, 10 piperazinyl, pyranyl, dihydropyranyl, tetrahydropyranyl, dioxanyl, thiopyranyl, dihydrothiopyranyl, tetrahydrothiopyranyl, morpholinyl, thiazinyl and the like. Examples for monocyclic 5- to 6-membered heteroaromatic rings include triazinyl, pyrazinyl, pyrimidyl, pyridazinyl, pyridyl, thienyl, furyl, pyrrolyl, pyrazolyl, imidazolyl, 15 triazolyl, tetrazolyl, thiazolyl, oxazolyl, thiadiazolyl, oxadiazolyl, isothiazolyl and isoxazolyl. With respect to the use according to the invention of the compounds of formula I, particular preference is given to the following meanings of the substituents, in each 20 case on their own or in combination: Preference is given to compounds of formula I, wherein A in formula I is a cyclic radical selected from phenyl, thienyl, furyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazoloyl, pyridyl, pyrimidinyl, pyrazinyl, and pyridazinyl and where the 25 cyclic radical may be unsubstituted or substituted as described above. In particular the aformentioned radicals are unsubstituted or substituted by 1, 2 or 3 radicals R a as defined above. Preferred radicals R a comprise halogen, CN, C 1
-C
4 -alkyl, C 1
-C
4 -alkoxy, C1-C4 30 haloalkoxy, Cl-C 4 -alkylthio and C 1
-C
4 -haloalkyl, in particular F, CI, methyl, methoxy, ethoxy, methylthio, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, trifluoromethoxy and difluoromethoxy. More preference is given to compounds of formula I, wherin A is a cyclic radical 35 selected from phenyl, thienyl, furyl, isoxazolyl, pyrazolyl, imidazolyl, pyrazinyl, pyrimidinyl and pyridyl, in particular from pyridyl, thienyl and phenyl, where the cyclic radical may be substituted by 1, 2 or 3 substuituents R a which are as defined above and which are preferably selected, independently of one another, from halogen, Cl-C4 alkyl, Cl-C 4 -alkoxy, C 1
-C
4 -haloalkoxy, C 1
-C
4 -alkylthio and C 1
-C
4 -haloalkyl, in particular WO 2006/058730 PCT/EP2005/012787 14 from F, CI, methyl, methoxy, ethoxy, methylthio, difluoromethyl, trifluoromethyl, 2,2,2 trifluoroethyl, trifluoromethoxy and difluoromethoxy. Examples of preferred radicals A comprise: 5 - 2-thienyl, 3-bromothien-2-yl, 4-bromothien-2-yl, 5-bromothien-2-yl, 4,5 dibromothien-2-yl, 3-chlorothien-2-yl, 4-chlorothien-2-yl, 5-chlorothien-2-yl, 3 chloro-4-methylthien-2-yl, 3-methylthien-2-yl, 4-methylthien-2-yl, 5-methylthien-2 yl, 3-methoxythien-2-yl, 3-methoxy-5-(trifluoromethyl)thien-2-yl, 3-ethoxy-5 (trifluoromethyl)thien-2-yl, 2-bromo-4,5-dimethylthien-2-yl, 10 - pyridin-2-yl, 6-methylthiopyridin-2-yl, 3-fluoropyridin-2-yl, 3-methoxypyridin-2-yl, 6-methylpyridin-2-yl, 5-nitropyridin-2-yl, 3-fluoropyridin-2-yl, 6-bromopyridin-2-yl, 6-chloropyridin-2-yl, 4-chloropyridin-2-yl, 3,6-dichloropyridin-2-yl, 6-fluoropyridin 2-yl, 5-(trifluoromethyl)pyridin-2-yl, 4-(trifluoromethyl)pyridin-2-yl, 6 (trifluoromethyl)pyridin-2-yl, 6-hydroxypyridin-2-yl, 6-methoxypyridin-2-yl, 3 15 hydroxypyridin-2-yl, 6-phenylpyridin-2-yl, pyridin-3-yl, 6-chloropyridin-3-yl, 2,6 dichloropyridin-3-yl, 5,6-dichloropyridin-3-yl, 2,6-dichloro-4-methylpyridin-3-yl, 6 fluoropyridin-3-yl, 6-bromopyridin-3-yl, 5-bromopyridin-3-yl, 2-phenoxypyridin-3 yl, 1-methyl-2-hydroxypyridin-3-yl, pyridin-4-yl, 2-chloropyridin-4-yl, 2,6 dichloropyridin-4-yl, 20 - phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2,4-difluorophenyl, 2,5 difluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,3 dichlorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 2 chloro-6-fluorophenyl, 2-chloro-4-fluorophenyl, 1,2,3,4,5-pentafluorophenyl, 2 bromophenyl, 3-bromophenyl, 4-bromophenyl, 5-bromo-2-chlorophenyl, 4-chloro 25 2-methylphenyl, 3-fluoro-4-methylphenyl, 2-methylphenyl, 3-methylphenyl, 4 methylphenyl, 2,6-dimethylphenyl, 2-(trifluoromethyl)phenyl, 3 (trifluoromethyl)phenyl, 4-(trifluoromethyl)phenyl, 2-fluoro-4 (trifluoromethyl)phenyl, 3,5-bis(trifluoromethyl)phenyl, 4-tert.-butyl-phenyl, 2 methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 3,4-dimethoxyphenyl, 3,4,5 30 trimethoxyphenyl, 2-ethoxyphenyl, 3-ethoxyphenyl, 4-ethoxyphenyl, 2-methoxy-3 (methylthio)phenyl, 2-nitrophenyl, 3-nitrophenyl, 4-nitrophenyl, 2-hydroxyphenyl, 3-hydroxyphenyl, 4-hydroxyphenyl, 4-hydroxy-3-methoxyphenyl, 2-fluoro-4 hydroxyphenyl, 2-aminophenyl, 3-aminophenyl, 4-aminophenyl, 6-amino-2 fluorophenyl, 4-(dimethylamino)phenyl, 4-phenylphenyl, 4-(methylsulfonyl)-2 35 nitrophenyl, - 5-methylpyrazin-2-yl, 3-aminopyrazin-2-yl, - 2-furyl, 5-bromofuran-2-yl, 2-methylfuran-3-yl - 5-isoxazolyl, 3-methylisoxazolyl, 3-(1-methylethyl)isoxazolyl, 5 (chloromethyl)isoxazolyl, 5-(hydroxymethyl)isoxazolyl, 40 - 1,3-bis(1,1,1-trifluoroeth-2-yl)pyrazol-4-yl, 1-methyl-3-(trifluoromethyl)pyrazol-5-yl, WO 2006/058730 PCT/EP2005/012787 15 - 3-methylimidazol-2-yl, 4-methylimididazol-5-yl, - 4-amino-2-methylpyrimidin-2-yl, 6-hydroxy-2-methylpyrimidin-4-yl, The cyclic radical may also be napthyl, 1,2,3,4-tetrahydroisochinolin-3-yl, 2 5 benzothienyl, benzo[1,3]-dioxol-5-yl, indolyl or benzimidazolyl, where the cyclic radical may be unsubstituted or substituted as described above. In particular the aformentioned radicals are unsubstituted or substituted by 1, 2 or 3 radicals R' as defined above. Examples of these radicals A comprise: - 3-hydroxynapth-2-yl, 2-benzothienyl, 3-chloro-2-benzothienyl, 1-naphthyl, 2 10 naphthyl, 3-indolyl, 2-benzimidazolyl, 6,7-dimethoxy-3-methyl-1,2,3,4 tetrahydroisochinolinyl. Another embodiment of the invention relates to compounds of the formula I wherein A is a 5- or 6-membered heterocyclic radical with 1 to 4 heteroatoms as ring members 15 which are selected, independently of one another, from O, N and S and may also have a carbonyl group as ring member, and may have 1, 2, 3, 4 or 5 substituents Ra as defined above. A very preferred embodiment of the invention relates to compounds of the formula I, 20 wherein A is thienyl, in particular 2-thienyl which is unsubstituted or substituted by 1, 2 or 3 radicals R a as defined above, the radicals R a being preferably selected, independently of one another, from halogen, C 1
-C
4 -alkyl, C 1
-C
4 -alkoxy, C 1
-C
4 -alkylthio,
C
1
-C
4 -haloalkoxy and C 1
-C
4 -haloalkyl, in particular from F, Cl, Br, methyl, methoxy, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, trifluoromethoxy and 25 difluoromethoxy. Another very preferred embodiment of the invention relates to compounds of the formula I, wherein A is furyl, in particular 2-furyl which is unsubstituted or substituted by 1, 2 or 3 radicals R a as defined above, the radicals R a being preferably selected, 30 independently of one another, from halogen, C 1
-C
4 -alkyl, C 1
-C
4 -alkoxy, Cl-C 4 -alkylthio,
C,-C
4 -haloalkoxy and C-C 4 -haloalkyl, in particular from F, CI, Br, methyl, methoxy, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, trifluoromethoxy and difluoromethoxy. 35 Another very preferred embodiment of the invention relates to compounds of the formula I, wherein A is pyridyl, in particular 2- or 3-pyridyl, more preferably 2-pyridyl which is unsubstituted or substituted by 1, 2 or 3 radicals R' as defined above, the radicals Ra being preferably selected, independently of one another, from halogen, Cj
C
4 -alkyl, C 1
-C
4 -alkoxy, C 1
-C
4 -alkylthio, C 1
-C
4 -haloalkoxy and C 1
-C
4 -haloalkyl, in WO 2006/058730 PCT/EP2005/012787 16 particular from F, CI, Br, methyl, methoxy, difluoromethyl, trifluoromethyl, 2,2,2 trifluoroethyl, trifluoromethoxy and difluoromethoxy. A further very preferred embodiment of the invention relates to compounds of the 5 formula I, wherein A is phenyl, which is unsubstituted or substituted by 1, 2 or 3 radicals R a as defined above, the radicals R a being preferably selected, independently of one another, from halogen, Cl-C 4 -alkyl, C 1
-C
4 -alkoxy, Cl 1
-C
4 -haloalkoxy, C1-C4 alkylthio and Cl-C 4 -haloalkyl, in particular from F, Cl, Br, methyl, methoxy, ethoxy, methylthio, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, trifluoromethoxy and 10 difluoromethoxy. X is preferably C=O. Q is preferably selected from the group consisting of a single bond, -CH 2 -, -CH 2
-CH
2 -, 15 -O-CH 2 -, -O-CH 2
-CH
2 -, O-CH 2
-CH
2
-CH
2 -, -NH-CH 2
-CH
2 -, -NH-C(0)-CH 2 -, -S-CH 2 -,
-S-CH
2
-CH
2 -, -O-CH(CH 3 )- and -S-CH(CH 3 )-, in particular from a single bond, -CH 2 -, -- OCH 2 -, -S-CH 2 -, -O-CH(CH 3 )- and -S-CH(CH 3 )-. The heteroatom of Q is preferably attached to A. More preferably Q is a single bond or -CH 2 -. 20 Preference is also given to compounds of the formula I, wherein the moiety A-Q is Cl-C 10 -alkyl, which may be substituted by 1 or 2 substituents selected from the group consisting of =0, OH, C 1
-C
4 -alkoxy, C-C 4 -alkylthio, halogen or C-C 4 -alkylcarbonyloxy, in particular from =0, OH and Cl-C 2 -alkoxy. Preferred examples of the moiety A-Q include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, 4-hydroxybutyl, 5 25 hydroxypentyl, 2,2-dimethoxyethyl, 2,2-diethoxyethyl, methoxycarbonylmethyl or ethoxycarbonylmethyl, especially methyl. In one embodiment of this invention R 1 is H, C-Co 0 -alkyl, C0 1 -Co 0 -haloalkyl, C3-C010 cycloalkyl, C3-Co 10 -halocycloalkyl, C2-C0 0 -alkenyl, C2-Co 10 -haloalkenyl, C 2
-C
1 0 -alkynyl and 30 C2-Co 10 -haloalkynyl. In this embodiment R' is preferably hydrogen, C0 1
-C
0 -alkyl, C1-Co0 haloalkyl, more preferably hydrogen, C 1
-C
4 -alkyl or C 1
-C
4 -haloalkyl, and especially hydrogen. In a further embodiment of this invention R' is selected from the group consisting of phenyl and a 5- or 6-membered heterocyclic radical with 1 to 4 heteroatoms which are selected, independently of one another, from O, N and S, it 35 being possible for phenyl and the 5- or 6-membered heterocyclic radical to be unsubstituted or substituted by 1, 2, 3, 4 or 5 substituents R a as defined above. In this embodiment preference is given to compounds I, wherein R 1 is pyridyl, in particular 3 pyridyl, C 3 -Co 10 -cycloalkyl, phenyl and more preferably C 3
-C
6 -cyclopropyl, WO 2006/058730 PCT/EP2005/012787 17
R
2 is preferably selected from hydrogen, halogen and CI-C 4 -alkyl, in particular from hydrogen, fluorine chlorine, bromine, methyl or ethyl.
R
3 is preferably selected from hydrogen, halogen and C 1
-C
4 -alkyl, with hydrogen being 5 more preferred. R 5 is preferably selected from hydrogen, Cl-Clo-alkyl, C 1 -Co 10 -haloalkyl, C 3 -Clo cycloalkyl, C 3 -Clo-halocycloalkyl, C 2 -Co 10 -alkenyl, C 2 -Co 10 -haloalkenyl, in particular from hydrogen and Cl-C 4 -alkyl. 10 In a further embodiment R 6 is selected from the group consisiting of H, Cl-Co 10 -alkyl, which is optionally substituted by CN or NO 2 , C0 1 -Co 10 -haloalkyl, C 3 -Cl 10 -cycloalkyl, C3 Clo 0 -halocycloalkyl, C 2 -Co 10 -alkenyl, C 2 -Co 10 -haloalkenyl, C 2 -Co 10 -alkynyl, C 2
-C
1 0 o haloalkynyl, C 1
-C
10 -alkylsulfinyl, C 1 -Co 10 -haloalkylsulfinyl, Cl-Co 10 -alkylsulfonyl, C1-Clo 15 haloalkylsulfonyl, C 1 -Co 10 -alkoxycarbonyl, C 1 -Co 10 -haloalkoxycarbonyl, C2-Co10 alkenyloxycarbonyl, C2-Co 10 -haloalkenyloxycarbonyl, C 1 -Co 10 -alkylcarbonyl, C4-Clo haloalkylcarbonyl, hydroxy-C 1 -Co 10 -alkyl, C 1 -Clo-alkoxy- C 1
-C
10 -alkyl, halo-Cl-Co 0 alkoxy-C 1 -Clo-alkyl, C-Co 10 -alkoxycarbonyl-C 1
-C
1 0 -alkyl, halo-C 1 -Co 10 -alkoxycarbonyl-C 1 C 10 o-alkyl, R 7
R
8 N-CO- and benzyl wherein benzyl may be substituted by 1, 2, 3, 4 or 5 20 substituents Rb as defined above. In this embodiment R 6 is preferably hydrogen, C 1
-C
4 alkyl, Cl-C 4 -haloalkyl, C 1
-C
4 -alkylsulfonyl, Cl-C 4 -alkylcarbonyl, C 1
-C
4 -alkylsulfonyl or
C
1
-C
4 -haloalkylsulfonyl, in particular hydrogen. Preference is also given to compounds of the formula I, wherein R 6 is C 1
-C
10 -alkylthio, 25 C 1 -Co 10 -haloalkylthio, C 1 -Co 10 -alkylcarbonyl, where the alkyl moiety of alkylcarbonyl is substituted by 1, 2 or 3 substituents selected from the group consisting of Cl-Cso alkylthio, phenylthio, phenyl and phenoxy, C 2
-C
10 -alkenylcarbonyl, benzoyl (CeH 5 -CO-),
C
3 -C lo-cycloalkylcarbonyl, R 6 a-CO
-
, wherein R 6 e a is Cl-C 4 -alkoxycarbonyl, phenoxy, naphthyl or a 5- or 6-membered heterocyclic radical with 1 to 4 heteroatoms which are 30 selected, independently of one another, from O, N and S, it being possible for phenoxy, naphthyl and the 5- or 6-membered heterocyclic radical to be unsubstituted or substituted by 1, 2, 3, 4 or 5 substituents R a as defined above. In this embodiment R 6 is preferably C1-C 4 -alkylcarbonyl, wherein the alkyl moiety of alkylcarbonyl is substituted by a radical selected from phenyl, C 1
-C
4 -alkylthio, phenylthio and phenoxy, such as 35 phenoxymethylcarbonyl, 2-methylsulfanylethylcarbonyl and phenylsulfanylmethylcarbonyl or benzoyl. Preference is also given to compounds of the formula I, wherein R 6 is a benzoyl or a radical of the formula R 6 a-C(O)
-
, wherein R ea is
C
1
-C
2 -alkoxycarbonyl, phenoxy, a 5- or 6-membered aromatic heterocyclic radical with 1 or 2 heteroatoms which are selected, independently of one another, from O, N and S, 40 it being possible for the 5- or 6-membered heterocyclic radical to be unsubstituted or WO 2006/058730 PCT/EP2005/012787 18 substituted by 1or 2 substituents R' as defined above. Example of preferred radicals Rea are phenoxy, 3-isoxazolyl, 5-isoxazolyl, 2-thienyl and 2-furyl and methoxycarbonyl. 5 Ar is preferably phenyl, which is unsubstituted or substituted by 1, 2, 3 or 4, in particular 1, 2 or 3 radicals Rc as defined above. A skilled person will appreciate that in case of R 4 being different from hydrogen, R 4 is one of the 1 to 4 radicals R c as defined above or R 4 together with R 2 is the aformentioned bivalent radical. 10 Another embodiment of the invention relates to compounds I, wherein Ar is an aromatic radical selected from phenyl, naphthyl, pyridyl, pyrimidyl, furyl and thienyl and wherein two radicals Rc which are bound to adjacent carbon atoms may form a O-CH 2 -O moiety, where in said moiety 1 or 2 hydrogen atoms may be replaced by a radical Rb as defined above. 15 In one embodiment the radical Rc is halogen, cyano, nitro, C 1
-C
10 -alkyl, C1-C1o0 haloalkyl, C 3 -Co 10 -cycloalkyl, C3-Co 10 -halocycloalkyl, C 2 -Co 10 -alkenyl, C 2
-C
1 0 -haloalkenyl,
C
2 -Co 10 -alkynyl, C3-Co 10 -haloalkynyl, Cl-Co 10 -alkoxy, C 1 -Co 10 -haloalkoxy, C 2
-C
1 0 -alkenyloxy,
C
2 -Co 10 -alkynyloxy, C 3 -Co 10 -haloalkynyloxy, Cl-Clo-alkylthio, C 1 -Co 10 -haloalkylthio, C01-C10 alkylsulfinyl, Cl-Co 10 -haloalkylsulfinyl, C-Co 10 -alkylsulfonyl, Cl-C 10 -haloalkylsulfonyl, 20 hydroxy, NR 7
R
8 , C 1 -Co 10 -alkoxycarbonyl, C 1 -Co 10 -haloalkoxycarbonyl, C2-Co10 alkenyloxycarbonyl, C 2 -Co 10 -haloalkenyloxycarbonyl, C0 1 -Co 10 -alkylcarbonyl, C4-C10 haloalkylcarbonyl, R 7
R
8 N-CO-, phenyl, benzyl and phenoxy, wherein phenyl, benzyl and phenoxy may be unsubstituted or substituted by 1, 2, 3, 4 or 5 substituents Rb as defined above. Preferably the radicals Rc are selected, independently of one another, 25 from halogen, CN, C 1
-C
4 -alkyl, C 1
-C
4 -alkoxy, C-C 4 -haloalkoxy and C-C 4 -haloalkyl, more preferably F, Cl, CN, C 1
-C
3 -alkoxy, in particular methoxy, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy and methyl. In another embodiment the radical Rc is C-Co 10 -alkylcarbonyl. 30 A further very preferred embodiment of the invention relates to compounds of the formula I, wherein Ar is furyl, in particular 2-furyl which is unsubstituted or substituted by 1 radical Rc as defined above or thienyl, in particular 2-thienyl, which may be unsubstituted or substituted by 1 radical Rc as defined above. 35 In a preferred embodiment of the invention the radical R 2 in formula I is a monovalent radical, i.e. R 2 and R 4 together do not form a bivalent radical. In this embodiment R 2 is preferably selected from hydrogen, halogen, C 1
-C
4 -alkyl, Cl-C 4 -alkoxy, C1-C4 haloalkoxy and C-C 4 -haloalkyl. More preferably R 2 is hydrogen, fluorine, chlorine bromine, methyl or ethyl. In this embodiment R 4 is hydrogen or a radical Rc as defined 40 above, in particular hydrogen. In this embodiment Ar in formula I is preferably phenyl, WO 2006/058730 PCT/EP2005/012787 19 which is unsubstituted or substituted by 1, 2, 3 or 4, in particular 1, 2 or 3 radicals RC as defined above. Another embodiment of the invention relates to compounds of the formula I, wherein R 4 5 together with R 2 is a bivalent radical Y as defined above and which is preferably selected from O, S, CH=N, O-CH 2 , O-C(0) or NH-C(O), where in the last 4 moieties either the carbon atom or the heteroatom is attached to the phenyl ring, in particular from O, S, O-CH 2 , and O-C(0), where in the two last moieties the heteroatom is attached to the phenyl ring. More preferably R 4 and R 2 together are an oxygen atom or 10 O-C(0) in particular O. In this embodiment Ar in formula I is preferably phenyl, which is unsubstituted or substituted by 1, 2 or 3, in particular 0, 1 or 2 radicals Rc as defined above. Apart from that, Rb is preferably selected from halogen, C 1
-C
4 -alkyl, C 1
-C
4 -alkoxy, Cj 15 C 4 -haloalkoxy and C-C 4 -haloalkyl. If present, R 7 , R 8 are preferably selected independently from one another from hydrogen and C 1
-C
4 -alkyl. 20 If present, R 9 is preferably selected from hydrogen, C 1
-C
4 -alkyl and C 1
-C
4 alkylcarbonyl, in particular hydrogen. If present, R 1 0 is preferably selected from hydrogen, halogen and C 1
-C
4 -alkyl, in particular hydrogen. 25 If present, R 1 ", R 12 are preferably selected independently from one another from hydrogen and C 1
-C
4 -alkyl, in particular hydrogen. If present, R 13 is preferably selected from hydrogen and C1-C 4 -alkyl, in particular 30 hydrogen. A very preferred embodiment of the invention relates to compounds of the general formula la:
SR
2 AII I (Rc)k (a) A" Q ,N \ 15 1 3 35 R R R WO 2006/058730 PCT/EP2005/012787 20 wherein k is 0, 1, 2 or 3, and wherein A, Q, R 1 , R 2 , R 3 , R 5 and Rc are as defined above. Amongst the compounds la those are preferred, wherein Q, A, R 1 , R 2 , R 3 , R 5 and Rc have the meanings given as preferred. 5 Examples of compounds la are given in the following tables 1 to 180: Table 1: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is H, R 5 is H and k is 0 (i.e. (RC)k is absent) and wherein Q and A are given in table A; 10 Table 2: Compounds of the formula la, wherein R' is H, R 3 is H, R 2 is H, R 5 is H and (RC)k is 4 fluoro and wherein Q and A are given in table A; 15 Table 3: Compounds of the formula la, wherein R' is H, R 3 is H, R 2 is H, R 5 is H and (Rc)k is 4 chloro and wherein Q and A are given table A; Table 4: 20 Compounds of the formula la, wherein R' is H, R 3 is H, R 2 is H, R 5 is H and (Rc)k is 3 fluoro and wherein Q and A are given in table A; Table 5: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is H, R 5 is H and (RC)k is 3 25 difluoromethoxy and wherein Q and A are given in table A; Table 6: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is H, R 5 is H and (RC)k is 3 trifluoromethyl and wherein Q and A are given in table A; 30 Table 7: Compounds of the formula la, wherein R' is H, R 3 is H, R 2 is H, R 5 is H and (Rc)k is 4 fluoro-3-trifluoromethyl and wherein Q and A are given in table A; 35 Table 8: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is H, R 5 is H and (Rc)k is 4 methoxy-3-trifluoromethyl and wherein Q and A are in given table A; Table 9: WO 2006/058730 PCT/EP2005/012787 21 Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is H, R 5 is H and (RC)k is 4 methylthio-3-trifluoromethyl and wherein Q and A are given in table A; Table 10: 5 Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is H, R 5 is H and (RC)k is 2-F and wherein Q and A are given in table A; Table 11: Compounds of the formula la, wherein R' is H, R 3 is H, R 2 is H, R , 5 is H and (RC)k is 2 10 CH 3 and wherein Q and A are given in table A; Table 12: Compounds of the formula la, wherein R' is H, R 3 is H, R 2 is H, R 5 is H and (RC)k is 2
OCH
3 and wherein Q and A are given in table A; 15 Table 13: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is H, R 5 is H and (RC)k is 2
CF
3 and wherein Q and A are given in table A; 20 Table 14: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is H, R 5 is H and (RC)k is 4
OCH
3 and wherein Q and A are given in table A; Table 15: 25 Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is H, R 5 is H and (RC)k is 2
OCHF
2 and wherein Q and A are given in table A; Table 16: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is F, R 5 is H and k is 0 (i.e. 30 (RC)k is absent) and wherein Q and A are given in table A; Table 17: Compounds of the formula la, wherein R' is H, R 3 is H, R 2 is F, R 5 is H and (RC)k is 4 fluoro and wherein Q and A are given in table A; 35 Table 18: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is F, R 5 is H and (RC)k is 4 chloro and wherein Q and A are given in table A; 40 Table 19: WO 2006/058730 PCT/EP2005/012787 22 Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is F, R 5 is H and (RC)k is 3 fluoro and wherein Q and A are given in table A; Table 20: 5 Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is F, R 5 is H and (RC)k is 3 difluoromethoxy and wherein Q and A are given in table A; Table 21: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is F, R 5 is H and (RC)k is 3 10 trifluoromethyl and wherein Q and A are given in table A; Table 22: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is F, R 5 is H and (RC)k is 4 fluoro-3-trifluoromethyl and wherein Q and A are given in table A; 15 Table 23: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is F, R 5 is H and (RC)k is 4 methoxy-3-trifluoromethyl and wherein Q and A are given in table A; 20 Table 24: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is F, R 5 is H and (Rc)k is 4 methylthio-3-trifluoromethyl and wherein Q and A are given in table A; Table 25: 25 Compounds of the formula la, wherein R' is H, R 3 is H, R 2 is F, R 5 is H and (RC)k is 2-F and wherein Q and A are given in table A; Table 26: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is F, R 5 is H and (RC)k is 2 30 CH 3 and wherein Q and A are given in table A; Table 27: Compounds of the formula la, wherein R' is H, R 3 is H, R 2 is F, R 5 is H and (Rc)k is 2
OCH
3 and wherein Q and A are given in table A; 35 Table 28: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is F, R 5 is H and (Rc)k is2
CF
3 and wherein Q and A are given in table A; 40 Table 29: WO 2006/058730 PCT/EP2005/012787 23 Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is F, R 5 is H and (Rc)k is 4
OCH
3 and wherein Q and A are given in table A; Table 30: 5 Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is F, R 5 is H and (RC)k is 2
OCHF
2 and wherein Q and A are given in table A; Table 31: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is CI, R 5 is H and k is 0 (i.e. 10 (RC)k is absent) and wherein Q and A are given in table A; Table 32: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is CI, R 5 is H and (RC)k is 4 fluoro and wherein Q and A are given in table A; 15 Table 33: Compounds of the formula la, wherein R' is H, and R 3 is H, R 2 is CI, R 5 is H and (RC)k is 4-chloro and wherein Q and A are given in table A; 20 Table 34: Compounds of the formula la, wherein R 1 is H, and R 3 is H, R 2 is CI, R 5 is H and (Rc)k is 3-fluoro and wherein Q and A are given in table A; Table 35: 25 Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is CI, R 5 is H and (RC)k is 3 difluoromethoxy and wherein Q and A are given in table A; Table 36: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is Cl, R 5 is H and (Rc)k is 3 30 trifluoromethyl and wherein Q and A are given in table A; Table 37: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is CI, R 5 is H and (RC)k is 4 fluoro-3-trifluoromethyl and wherein Q and A are given in table A; 35 Table 38: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is CI, R 5 is H and (RC)k is 4 methoxy-3-trifluoromethyl and wherein Q and A are given in table A; 40 Table 39: WO 2006/058730 PCT/EP2005/012787 24 Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is CI, R' is H and (RC)k is 4 methylthio-3-trifluoromethyl and wherein Q and A are given in table A; Table 40: 5 Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is CI, R 5 is H and (Rc)k is 2-F and wherein Q and A are given in table A; Table 41: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is CI, R 5 is H and (RC)k is 2 10 CH 3 and wherein Q and A are given in table A; Table 42: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is CI, R 5 is H and (Rc)k is 2
OCH
3 and wherein Q and A are given in table A; 15 Table 43: Compounds of the formula la, wherein R' is H, R 3 is H, R 2 is Cl, R 5 is H and (Rc)k is 2
CF
3 and wherein Q and A are given in table A; 20 Table 44: Compounds of the formula la, wherein R' is H, R 3 is H, R 2 is Cl, R 5 is H and (Rc)k is 4
OCH
3 and wherein Q and A are given in table A; Table 45: 25 Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is CI, R 5 is H and (Rc)k is 2
OCHF
2 and wherein Q and A are given in table A; Table 46: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is Br, R 5 is H and k is 0 (i.e. 30 (RC)k is absent) and wherein Q and A are given in table A; Table 47: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is Br, R 5 is H and (Rc)k is 4 fluoro and wherein Q and A are given in table A; 35 Table 48: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is Br, R 5 is H and (Rc)k is 4 chloro and wherein Q and A are given in table A; 40 Table 49: WO 2006/058730 PCT/EP2005/012787 25 Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is B, R' is H r and (RC)k is 3 fluoro and wherein Q and A are given in table A; Table 50: 5 Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is Br, R 5 is H and (RC)k is 3 difluoromethoxy and wherein Q and A are given in table A; Table 51: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is Br, R 5 is H and (Rc)k is 3 10 trifluoromethyl and wherein Q and A are given in table A; Table 52: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is Br, R 5 is H and (RC)k is 4 fluoro-3-trifluoromethyl and wherein Q and A are given in table A; 15 Table 53: Compounds of the formula la, wherein R' is H, R 3 is H, R 2 is Br, R 5 is H and (RC)k is 4 methoxy-3-trifluoromethyl and wherein Q and A are given in table A; 20 Table 54: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is Br, R 5 is H and (RC)k is 4 methylthio-3-trifluoromethyl and wherein Q and A are given in table A; Table 55: 25 Compounds of the formula la, wherein R' is H, R 3 is H, R 2 is Br, R 5 is H and (RC)k is 2-F and wherein Q and A are given in table A; Table 56: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is Br, R 5 is H and (RC)k is 2 30 CH 3 and wherein Q and A are given in table A; Table 57: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is Br, R 5 is H and (Rc)k is 2
OCH
3 and wherein Q and A are given in table A; 35 Table 58: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is Br, R 5 is H and (RC)k is2
CF
3 and wherein Q and A are given in table A; 40 Table 59: WO 2006/058730 PCT/EP2005/012787 26 Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is Br, R' is H and (RC)k is 4
OCH
3 and wherein Q and A are given in table A; Table 60: 5 Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is Br, R 5 is H and (RC)k is 2
OCHF
2 and wherein Q and A are given in table A; Table 61: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is CH 3 , R 5 is H and k is 0 10 (i.e. (RC)k is absent) and wherein Q and A are given in table A; Table 62: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is CH 3 , R 5 is H and (R 0 )k is 4-fluoro and wherein Q and A are given in table A; 15 Table 63: Compounds of the formula la, wherein R' is H, R 3 is H, R 2 is CH 3 , R 5 is H and (Rc)k is 4-chloro and wherein Q and A are given in table A; 20 Table 64: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is CH 3 , R 5 is H and (Rc)k is 3-fluoro and wherein Q and A are given in table A; Table 65: 25 Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is CH 3 , R is H and (Rc)k is 3-difluoromethoxy and wherein Q and A are given in table A; Table 66: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is CH 3 , R 5 is H and (RC)k is 30 3-trifluoromethyl and wherein Q and A are given in table A; Table 67: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is CH 3 , Re is H and (Rc)k is 4-fluoro-3-trifluoromethyl and wherein Q and A are given in table A; 35 Table 68: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is CH 3 , R 5 is H and (RC)k is 4-methoxy-3-trifluoromethyl and wherein Q and A are given in table A; and 40 Table 69: WO 2006/058730 PCT/EP2005/012787 27 Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is CH 3 , R 5 is H and (RC)k is 4-methylthio-3-trifluoromethyl and wherein Q and A are in given table A. Table 70: 5 Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is CH 3 , R 5 is H and (RC)k is 2-F and wherein Q and A are given in table A; Table 71: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is CH 3 , R 5 is H and (Rc)k is 10 2-CH 3 and wherein Q and A are given in table A; Table 72: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is CH 3 , R 5 is H and (RC)k is 2-OCH 3 and wherein Q and A are given in table A; 15 Table 73: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is CH 3 , R 5 is H and (RC)k is 2-CF 3 and wherein Q and A are given in table A; 20 Table 74: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is CH 3 , R 5 is H and (Rc)k is 4-OCH 3 and wherein Q and A are given in table A; Table 75: 25 Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is CH 3 , R 5 is H and (RC)k is 2-OCHF 2 and wherein Q and A are given in table A; Table 76: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is CH 2
CH
3 , R6 is H and k is 0 30 (i.e. (Rc)k is absent) and wherein Q and A are given in table A; Table 77: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is CH 2
CH
3 , R 5 is H and (Rc)k is 4-fluoro and wherein Q and A are given in table A; 35 Table 78: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is CH 2
CH
3 , R 5 is H and (RC)k is 4-chloro and wherein Q and A are given in table A; 40 Table 79: WO 2006/058730 PCT/EP2005/012787 28 Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is CH 2
CH
3 , R 5 is H and (RC)k is 3-fluoro and wherein Q and A are given in table A; Table 80: 5 Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is CH 2
CH
3 , R 5 is H and (RC)k is 3-difluoromethoxy and wherein Q and A are given in table A; Table 81: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is CH 2
CH
3 , R 5 is H and 10 (RC)k is 3-trifluoromethyl and wherein Q and A are given in table A; Table 82: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is CH 2
CH
3 , R 5 is H and (Rc)k is 4-fluoro-3-trifluoromethyl and wherein Q and A are given in table A; 15 Table 83: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is CH 2 CH3, R 5 is H and (Rc)k is 4-methoxy-3-trifluoromethyl and wherein Q and A are given in table A; 20 Table 84: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is CH 2
CH
3 , R 5 is H and (RC)k is 4-methylthio-3-trifluoromethyl and wherein Q and A are given in table A; Table 85: 25 Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is CH 2
CH
3 , R 5 is H and (RC)k is 2-F and wherein Q and A are given in table A; Table 86: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is CH 2
CH
3 , R 5 is H and (RC)k 30 is 2-CH 3 and wherein Q and A are given in table A; Table 87: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is CH 2
CH
3 , R 5 is H and (RC)k is 2-OCH 3 and wherein Q and A are given in table A; 35 Table 88: Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is CH 2
CH
3 , R" is H and (Rc)k is2-CF 3 and wherein Q and A are given in table A; 40 Table 89: WO 2006/058730 PCT/EP2005/012787 29 Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is CH 2
CH
3 , R 5 is H and (RC)k is 4-OCH 3 and wherein Q and A are given in table A;. Table 90: 5 Compounds of the formula la, wherein R 1 is H, R 3 is H, R 2 is CH 2
CH
3 , R 5 is H and (RC)k is 2-OCHF 2 and wherein Q and A are given in table A; Tables 91 to 180: Compounds of the formula la, wherein R 1 , R 2 , R 3 and (RC)k are as defined in one of the 10 tables 1 to 90, Q and A are given in table A and R 5 is methyl instead of hydrogen. Table A: A Q 1 2-thienyl 2 3-bromothien-2-yl 3 4-bromothien-2-yl 4 5-bromothien-2-yl 5 4,5-dibromthien-2-yl 6 3-chlorothien-2-yl 7 4-chlorothien-2-yl 8 5-chlorothien-2-yl 9 3-chloro-4-methylthien-2-yl 10 3-methylthien-2-yl 11 4-methylthien-2-yl 12 5-methylthien-2-yl 13 3-methoxythien-2-yl 14 3-methoxy-5-(trifluoromethyl)thien-2-yl 15 3-ethoxy-5-(trifluoromethyl)thien-2-yl 16 2-bromo-4,5-dimethylthien-2-yl 17 pyridin-2-yl 18 6-methylthiopyridin-2-yl 19 3-fluoropyridin-2-yl 20 3-methoxypyridin-2-yl 21 6-methylpyridin-2-yl 22 5-nitropyridin-2-yl 23 3-fluoropyridin-2-yl 24 6-bromopyridin-2-yl 25 6-chloropyridin-2-yl WO 2006/058730 PCT/EP2005/012787 30 AQ 26 4-chloropyridin-2-yl 27 3,6-dichloropyridin-2-y 28 6-fluoropyridin-2-yi__________ 29 5-(trifluoromethyl)pyridin-2-y _________ 30 4-(trifluoromethyl)pyrid in-2-yI 31 6-(trifluoromethyl)pyrid in-2-yi __________ 32 6-hydroxypyridin-2-y 33 6-methoxypyridin-2-yI 34 3-hydroxypyridin-2-yI 35 6-phenylpyridin-2-yi 36 pyridin-3-yi 37 6-chloropyridin-3-yi 38 2,6-dichloropyridin-3-yi 39 5,6-dichloropyridin-3-yl _________ 40 2,6-dichloro-4-methylpyridin-3-yI 41 6-fluoropyridin-3-yI 42 6-bromopyridin-3-yI 43 5-bromopyridin-3-yI 44 2-phenoxypyridin-3-y 45 1 -methyl-2-hydroxypyridin-3-yi 46 pyridin-4-yi 47 2-chloropyridin-4-y 48 2,6-dichloropyridin-4-yi 49 phenyl 50 2-fluorophenyl 51 3-fluorophenyl 52 4-fluorophenyl 53 2,4-difluorophenyl 54 2,5-difluorophenyl __________ 55 2-chlorophenyl 56 3-chlorophenyl 57 4-chlorophenyl __________ 58 2,3-dichlorophenyl __________ 59 2,4-dichlorophenyl 60 2,5-dichiorophenyl 61 2,6-dichlorophenyl 62 2-chioro-6-fluorophenyl __________ 63 2-chloro-4-fluorophenyl
__________
WO 2006/058730 PCT/EP2005/012787 31 A Q 64 1,2,3,4,5-pentafluorophenyl 65 2-bromophenyl 66 3-bromophenyl 67 4-bromophenyl 68 5-bromo-2-chlorophenyl 69 4-chloro-2-methylphenyl 70 3-fluoro-4-methylphenyl 71 2-methylphenyl 72 3-methylphenyl 73 4-methylphenyl 74 2,6-dimethylphenyl 75 2-(trifluoromethyl)phenyl 76 3-(trifluoromethyl)phenyl 77 4-(trifluoromethyl)phenyl 78 2-fluoro-4-(trifluoromethyl)phenyl 79 3,5-bis(trifluoromethyl)phenyl 80 4-tert.-butyl-phenyl 81 2-methoxyphenyl 82 3-methoxyphenyl 83 4-methoxyphenyl 84 3,4-dimethoxyphenyl 85 3,4,5-trimethoxyphenyl 86 2-ethoxyphenyl 87 3-ethoxyphenyl 88 4-ethoxyphenyl 89 2-methoxy-3-(methylthio)phenyl 90 2-nitrophenyl 91 3-nitrophenyl 92 4-nitrophenyl 93 2-hydroxyphenyl 94 3-hydroxyphenyl 95 4-hydroxyphenyl 96 4-hydroxy-3-methoxyphenyl 97 2-fluoro-4-hydroxyphenyl 98 2-aminophenyl 99 3-aminophenyl 100 4-aminophenyl 101 6-amino-2-fluorophenyl WO 2006/058730 PCT/EP2005/012787 32 A Q 102 4-(dimethylamino)phenyl 103 4-phenylphenyl 104 4-(methylsulfonyl)-2-nitrophenyl 105 5-methylpyrazin-2-yl 106 3-aminopyrazin-2-yl 107 2-furyl 108 5-bromofuran-2-yl 109 2-methylfuran-3-yl 110 5-isoxazolyl 111 3-methylisoxazolyl 112 3-(1 -methylethyl)isoxazolyl 113 5-(chloromethyl)isoxazolyl 114 5-(hydroxymethyl)isoxazoly 115 1,3-bis( 1,,1 -trifluoroeth-2-yl)pyrazol-4-yl 116 1 -methyl-3-(trifluoromethyl)pyrazol-5-yl 117 3-methylimidazol-2-yl 118 4-methylimididazol-5-yl 119 4-amino-2-methylpyrimidin-2-yl 120 6-hydroxy-2-methylpyrimidin-4-yl 121 3-hydroxynapth-2-yl 122 2-benzothienyl 123 3-chloro-2-benzothienyl 124 1 -naphthyl 125 2-naphthyl 126 3-indolyl 127 2-benzimidazolyl 128 6,7-dimethoxy-3-methyl-1,2,3,4- tetrahydroisochinolin-3-yl 129 2-thienyl
CH
2 130 3-bromothien-2-yl CH 2 131 4-bromothien-2-yl
CH
2 132 5-bromothien-2-yl CH 2 133 4,5-dibromthien-2-yl
CH
2 134 3-chlorothien-2-yl
CH
2 135 4-chlorothien-2-yl
CH
2 136 5-chlorothien-2-yl
CH
2 137 3-chloro-4-methylthien-2-yl
CH
2 138 3-methylthien-2-yl CH 2 WO 2006/058730 PCT/EP2005/012787 33 A Q 139 4-methylthien-2-yl CH 2 140 5-methylthien-2-yl CH 2 141 3-methoxythien-2-yl CH 2 142 3-methoxy-5-(trifluoromethyl)thien-2-yl CH 2 143 3-ethoxy-5-(trifluoromethyl)thien-2-yl
CH
2 144 2-bromo-4,5-dimethylthien-2-yl CH 2 145 pyridin-2-yl
CH
2 146 6-methylthiopyridin-2-yl CH 2 147 3-fluoropyridin-2-yl
CH
2 148 3-methoxypyridin-2-yl
CH
2 149 6-methylpyridin-2-yl
CH
2 150 5-nitropyridin-2-yl CH 2 151 3-fluoropyridin-2-yl
CH
2 152 6-bromopyridin-2-yl
CH
2 153 6-chloropyridin-2-yl
CH
2 154 4-chloropyridin-2-yl
CH
2 155 3,6-dichloropyridin-2-yl
CH
2 156 6-fluoropyridin-2-yl
CH
2 157 5-(trifluoromethyl)pyridin-2-yl CH 2 158 4-(trifluoromethyl)pyridin-2-yl CH 2 159 6-(trifluoromethyl)pyridin-2-yl
CH
2 160 6-hydroxypyridin-2-yl
CH
2 161 6-methoxypyridin-2-yl
CH
2 162 3-hydroxypyridin-2-yl
CH
2 163 6-phenylpyridin-2-yl
CH
2 164 pyridin-3-yl
CH
2 165 6-chloropyridin-3-yl
CH
2 166 2,6-dichloropyridin-3-yl
CH
2 167 5,6-dichloropyridin-3-yl
CH
2 168 2,6-dichloro-4-methylpyridin-3-yl
CH
2 169 6-fluoropyridin-3-yl CH 2 170 6-bromopyridin-3-yl CH 2 171 5-bromopyridin-3-yl CH 2 172 2-phenoxypyridin-3-yl CH 2 173 1-methyl-2-hydroxypyridin-3-yl CH 2 174 pyridin-4-yl CH 2 175 2-chloropyridin-4-yl
CH
2 176 2,6-dichloropyridin-4-yl CH 2 WO 2006/058730 PCT/EP2005/012787 34 A Q 177 phenyl
CH
2 178 2-fluorophenyl
CH
2 179 3-fluorophenyl
CH
2 180 4-fluorophenyl
CH
2 181 2,4-difluorophenyl
CH
2 182 2,5-difluorophenyl
CH
2 183 2-chlorophenyl
CH
2 184 3-chlorophenyl
CH
2 185 4-chlorophenyl
CH
2 186 2,3-dichlorophenyl
CH
2 187 2,4-dichlorophenyl
CH
2 188 2,5-dichlorophenyl
CH
2 189 2,6-dichlorophenyl
CH
2 190 2-chloro-6-fluorophenyl
CH
2 191 2-chloro-4-fluorophenyl
CH
2 192 1,2,3,4,5-pentafluorophenyl
CH
2 193 2-bromophenyl
CH
2 194 3-bromophenyl
CH
2 195 4-bromophenyl
CH
2 196 5-bromo-2-chlorophenyl
CH
2 197 4-chloro-2-methylphenyl
CH
2 198 3-fluoro-4-methylphenyl
CH
2 199 2-methylphenyl
CH
2 200 3-methylphenyl
CH
2 201 4-methylphenyl
CH
2 202 2,6-dimethylphenyl
CH
2 203 2-(trifluoromethyl)phenyl
CH
2 204 3-(trifluoromethyl)phenyl
CH
2 205 4-(trifluoromethyl)phenyl
CH
2 206 2-fluoro-4-(trifluoromethyl)phenyl
CH
2 207 3,5-bis(trifluoromethyl)phenyl
CH
2 208 4-tert.-butyl-phenyl
CH
2 209 2-methoxyphenyl
CH
2 210 3-methoxyphenyl
CH
2 211 4-methoxyphenyl
CH
2 212 3,4-dimethoxyphenyl
CH
2 213 3,4,5-trimethoxyphenyl
CH
2 214 2-ethoxyphenyl
CH
2 WO 2006/058730 PCT/EP2005/012787 35 A Q 215 3-ethoxyphenyl CH 2 216 4-ethoxyphenyl CH 2 217 2-methoxy-3-(methylthio)phenyl CH 2 218 2-nitrophenyl CH 2 219 3-nitrophenyl CH 2 220 4-nitrophenyl CH 2 221 2-hydroxyphenyl CH 2 222 3-hydroxyphenyl CH 2 223 4-hydroxyphenyl CH 2 224 4-hydroxy-3-methoxyphenyl CH 2 225 2-fluoro-4-hydroxyphenyl CH 2 226 2-aminophenyl CH 2 227 3-aminophenyl CH 2 228 4-aminophenyl CH 2 229 6-amino-2-fluorophenyl CH 2 230 4-(dimethylamino)phenyl CH 2 231 4-phenylphenyl CH 2 232 4-(methylsulfonyl)-2-nitrophenyl CH 2 233 5-methylpyrazin-2-yl CH 2 234 3-aminopyrazin-2-yl CH 2 235 2-furyl CH 2 236 5-bromofuran-2-yl CH 2 237 2-methylfuran-3-yl CH 2 238 5-isoxazolyl CH 2 239 3-methylisoxazolyl CH 2 240 3-(1 -methylethyl)isoxazolyl CH 2 241 5-(chloromethyl)isoxazolyl CH 2 242 5-(hydroxymethyl)isoxazolyl CH 2 243 1,3-bis(1,1,1 -trifluoroeth-2-yl)pyrazol-4-yl CH 2 244 1-methyl-3-(trifluoromethyl)pyrazol-5-yl CH 2 245 3-methylimidazol-2-yl CH 2 246 4-methylimididazol-5-yl CH 2 247 4-amino-2-methylpyrimidin-2-yl CH 2 248 6-hydroxy-2-methylpyrimidin-4-yl CH 2 249 3-hydroxynapth-2-yl CH 2 250 2-benzothienyl CH 2 251 3-chloro-2-benzothienyl CH 2 252 1-naphthyl CH 2 WO 2006/058730 PCT/EP2005/012787 36 A Q 253 2-naphthyl CH 2 254 3-indolyl CH 2 255 2-benzimidazolyl CH 2 256 6,7-dimethoxy-3-methyl-1,2,3,4- CH 2 tetrahydroisochinolin-3-yl 257 2-thienyl CH 2
CH
2 258 3-bromothien-2-yl CH 2
CH
2 259 4-bromothien-2-yl CH 2
CH
2 260 5-bromothien-2-yl CH 2
CH
2 261 4,5-dibromthien-2-yl CH 2
CH
2 262 3-chlorothien-2-yl CH 2
CH
2 263 4-chlorothien-2-yl CH 2
CH
2 264 5-chlorothien-2-yl CH 2
CH
2 265 3-chloro-4-methylthien-2-yl CH 2
CH
2 266 3-methylthien-2-yl CH 2
CH
2 267 4-methylthien-2-yl CH 2
CH
2 268 5-methylthien-2-yl CH 2
CH
2 269 3-methoxythien-2-yl CH 2
CH
2 270 3-methoxy-5-(trifluoromethyl)thien-2-yl CH 2
CH
2 271 3-ethoxy-5-(trifluoromethyl)thien-2-yl CH 2
CH
2 272 2-bromo-4,5-dimethylthien-2-yl CH 2
CH
2 273 pyridin-2-yl CH 2
CH
2 274 6-methylthiopyridin-2-yl CH 2
CH
2 275 3-fluoropyridin-2-yl CH 2
CH
2 276 3-methoxypyridin-2-yl CH 2
CH
2 277 6-methylpyridin-2-yl CH 2
CH
2 278 5-nitropyridin-2-yl CH 2
CH
2 279 3-fluoropyridin-2-yl CH 2
CH
2 280 6-bromopyridin-2-yl CH 2
CH
2 281 6-chloropyridin-2-yl CH 2
CH
2 282 4-chloropyridin-2-yl CH 2
CH
2 283 3,6-dichloropyridin-2-yl CH 2
CH
2 284 6-fluoropyridin-2-yl CH 2
CH
2 285 5-(trifluoromethyl)pyridin-2-yl CH 2
CH
2 286 4-(trifluoromethyl)pyridin-2-yl CH 2
CH
2 287 6-(trifluoromethyl)pyridin-2-yl CH 2
CH
2 288 6-hydroxypyridin-2-yl CH 2
CH
2 289 6-methoxypyridin-2-yl CH 2
CH
2 WO 2006/058730 PCT/EP2005/012787 37 A Q 290 3-hydroxypyridin-2-yl CH 2
CH
2 291 6-phenylpyridin-2-yl CH 2
CH
2 292 pyridin-3-yl CH 2
CH
2 293 6-chloropyridin-3-yl CH 2
CH
2 294 2,6-dichloropyridin-3-yl CH 2
CH
2 295 5,6-dichloropyridin-3-yl CH 2
CH
2 296 2,6-dichloro-4-methylpyridin-3-yl CH 2
CH
2 297 6-fluoropyridin-3-yl CH 2
CH
2 298 6-bromopyridin-3-yl CH 2
CH
2 299 5-bromopyridin-3-yl CH 2
CH
2 300 2-phenoxypyridin-3-yl CH 2
CH
2 301 1-methyl-2-hydroxypyridin-3-yl CH 2
CH
2 302 pyridin-4-yl CH 2
CH
2 303 2-chloropyridin-4-yl CH 2
CH
2 304 2,6-dichloropyridin-4-yl CH 2
CH
2 305 phenyl CH 2
CH
2 306 2-fluorophenyl CH 2
CH
2 307 3-fluorophenyl CH 2
CH
2 308 4-fluorophenyl CH 2
CH
2 309 2,4-difluorophenyl CH 2
CH
2 310 2,5-difluorophenyl CH 2
CH
2 311 2-chlorophenyl CH 2
CH
2 312 3-chlorophenyl CH 2
CH
2 313 4-chlorophenyl CH 2
CH
2 314 2,3-dichlorophenyl CH 2
CH
2 315 2,4-dichlorophenyl CH 2
CH
2 316 2,5-dichlorophenyl CH 2
CH
2 317 2,6-dichlorophenyl CH 2
CH
2 318 2-chloro-6-fluorophenyl CH 2
CH
2 319 2-chloro-4-fluorophenyl CH 2
CH
2 320 1,2,3,4,5-pentafluorophenyl CH 2
CH
2 321 2-bromophenyl CH 2
CH
2 322 3-bromophenyl CH 2
CH
2 323 4-bromophenyl CH 2
CH
2 324 5-bromo-2-chlorophenyl CH 2
CH
2 325 4-chloro-2-methylphenyl CH 2
CH
2 326 3-fluoro-4-methylphenyl CH 2
CH
2 327 2-methylphenyl CH 2
CH
2 WO 2006/058730 PCT/EP2005/012787 38 A Q 328 3-methylphenyl CH 2
CH
2 329 4-methylphenyl CH 2
CH
2 330 2,6-dimethylphenyl CH 2
CH
2 331 2-(trifluoromethyl)phenyl CH 2
CH
2 332 3-(trifluoromethyl)phenyl CH 2
CH
2 333 4-(trifluoromethyl)phenyl CH 2
CH
2 334 2-fluoro-4-(trifluoromethyl)phenyl CH 2
CH
2 335 3,5-bis(trifluoromethyl)phenyl CH 2
CH
2 336 4-tert.-butyl-phenyl CH 2
CH
2 337 2-methoxyphenyl CH 2
CH
2 338 3-methoxyphenyl CH 2
CH
2 339 4-methoxyphenyl CH 2
CH
2 340 3,4-dimethoxyphenyl CH 2
CH
2 341 3,4,5-trimethoxyphenyl CH 2
CH
2 342 2-ethoxyphenyl CH 2
CH
2 343 3-ethoxyphenyl CH 2
CH
2 344 4-ethoxyphenyl CH 2
CH
2 345 2-methoxy-3-(methylthio)phenyl CH 2
CH
2 346 2-nitrophenyl CH 2
CH
2 347 3-nitrophenyl CH 2
CH
2 348 4-nitrophenyl CH 2
CH
2 349 2-hydroxyphenyl CH 2
CH
2 350 3-hydroxyphenyl CH 2
CH
2 351 4-hydroxyphenyl CH 2
CH
2 352 4-hydroxy-3-methoxyphenyl CH 2
CH
2 353 2-fluoro-4-hydroxyphenyl CH 2
CH
2 354 2-aminophenyl CH 2
CH
2 355 3-aminophenyl CH 2
CH
2 356 4-aminophenyl CH 2
CH
2 357 6-amino-2-fluorophenyl CH 2
CH
2 358 4-(dimethylamino)phenyl CH 2
CH
2 359 4-phenylphenyl CH 2
CH
2 360 4-(methylsulfonyl)-2-nitrophenyl CH 2
CH
2 361 5-methylpyrazin-2-yl CH 2
CH
2 362 3-aminopyrazin-2-yl CH 2
CH
2 363 2-furyl CH 2
CH
2 364 5-bromofuran-2-yl CH 2
CH
2 365 2-methylfuran-3-yl CH 2
CH
2 WO 2006/058730 PCT/EP2005/012787 39 A Q 366 5-isoxazolyl
CH
2
CH
2 367 3-methylisoxazolyl
CH
2
CH
2 368 3-(1 -methylethyl)isoxazolyl
CH
2
CH
2 369 5-(chloromethyl)isoxazolyI
CH
2
CH
2 370 5-(hydroxymethyl)isoxazolyl
CH
2
CH
2 371 1,3-bis(1,1,1-trifluoroeth-2-yl)pyrazol-4-yl
CH
2
CH
2 372 1 -methyl-3-(trifluoromethyl)pyrazol-5-yl
CH
2
CH
2 373 3-methylimidazol-2-yl
CH
2
CH
2 374 4-methylimididazol-5-yl
CH
2
CH
2 375 4-amino-2-methylpyrimidin-2-yl
CH
2
CH
2 376 6-hydroxy-2-methylpyrimidin-4-yl
CH
2
CH
2 377 3-hydroxynapth-2-yl
CH
2
CH
2 378 2-benzothienyl
CH
2
CH
2 379 3-chloro-2-benzothienyl
CH
2
CH
2 380 1-naphthyl
CH
2
CH
2 381 2-naphthyl
CH
2
CH
2 382 3-indolyl
CH
2
CH
2 383 2-benzimidazolyl
CH
2
CH
2 384 6,7-dimethoxy-3-methyl-1,2,3,4-
CH
2
CH
2 tetrahydroisochinolin-3-yl 385 2-thienyl
OCH
2 386 3-bromothien-2-yl
OCH
2 387 4-bromothien-2-yl
OCH
2 388 5-bromothien-2-yl
OCH
2 389 4,5-dibromthien-2-yl
OCH
2 390 3-chlorothien-2-yl
OCH
2 391 4-chlorothien-2-yl
OCH
2 392 5-chlorothien-2-yl
OCH
2 393 3-chloro-4-methylthien-2-yl
OCH
2 394 3-methylthien-2-yl
OCH
2 395 4-methylthien-2-yl
OCH
2 396 5-methylthien-2-yl
OCH
2 397 3-methoxythien-2-yl
OCH
2 398 3-methoxy-5-(trifluoromethyl)thien-2-yl
OCH
2 399 3-ethoxy-5-(trifluoromethyl)thien-2-yl
OCH
2 400 2-bromo-4,5-dimethylthien-2-yl
OCH
2 401 pyridin-2-yl
OCH
2 402 6-methylthiopyridin-2-yl
OCH
2 WO 2006/058730 PCT/EP2005/012787 40 A Q 403 3-fluoropyridin-2-yl OCH2 404 3-methoxypyridin-2-yl OCH2 405 6-methylpyridin-2-yl OCH2 406 5-nitropyridin-2-yl
OCH
2 407 3-fluoropyridin-2-yl
OCH
2 408 6-bromopyridin-2-yl
OCH
2 409 6-chloropyridin-2-yl
OCH
2 410 4-chloropyridin-2-yl
OCH
2 411 3,6-dichloropyridin-2-yl OCH2 412 6-fluoropyridin-2-yl
OCH
2 413 5-(trifluoromethyl)pyridin-2-yl OCH2 414 4-(trifluoromethyl)pyridin-2-yl OCH2 415 6-(trifluoromethyl)pyridin-2-yl
OCH
2 416 6-hydroxypyridin-2-yl OCH2 417 6-methoxypyridin-2-yl OCH2 418 3-hydroxypyridin-2-yl OCH2 419 6-phenylpyridin-2-yl OCH2 420 pyridin-3-yl
OCH
2 421 6-chloropyridin-3-yl OCH2 422 2,6-dichloropyridin-3-yl
OCH
2 423 5,6-dichloropyridin-3-yl OCH2 424 2,6-dichloro-4-methylpyridin-3-yl
OCH
2 425 6-fluoropyridin-3-yl OCH2 426 6-bromopyridin-3-yl OCH2 427 5-bromopyridin-3-yl
OCH
2 428 2-phenoxypyridin-3-yl
OCH
2 429 1-methyl-2-hydroxypyridin-3-yl
OCH
2 430 pyridin-4-yl
OCH
2 431 2-chloropyridin-4-yl
OCH
2 432 2,6-dichloropyridin-4-yl OCH2 433 phenyl OCH2 434 2-fluorophenyl
OCH
2 435 3-fluorophenyl OCH2 436 4-fluorophenyl
OCH
2 437 2,4-difluorophenyl
OCH
2 438 2,5-difluorophenyl
OCH
2 439 2-chlorophenyl OCH2 440 3-chlorophenyl OCH2 WO 2006/058730 PCT/EP2005/012787 41 A Q 441 4-chlorophenyl OCH 2 442 2,3-dichlorophenyl OCH 2 443 2,4-dichlorophenyl OCH 2 444 2,5-dichlorophenyl OCH 2 445 2,6-dichlorophenyl OCH 2 446 2-chloro-6-fluorophenyl OCH 2 447 2-chloro-4-fluorophenyl OCH 2 448 1,2,3,4,5-pentafluorophenyl OCH 2 449 2-bromophenyl OCH 2 450 3-bromophenyl OCH 2 451 4-bromophenyl OCH 2 452 5-bromo-2-chlorophenyl OCH 2 453 4-chloro-2-methylphenyl OCH 2 454 3-fluoro-4-methylphenyl OCH 2 455 2-methylphenyl OCH 2 456 3-methylphenyl OCH 2 457 4-methylphenyl OCH 2 458 2,6-dimethylphenyl OCH 2 459 2-(trifluoromethyl)phenyl OCH 2 460 3-(trifluoromethyl)phenyl OCH 2 461 4-(trifluoromethyl)phenyl OCH 2 462 2-fluoro-4-(trifluoromethyl)phenyl OCH 2 463 3,5-bis(trifluoromethyl)phenyl OCH 2 464 4-tert.-butyl-phenyl OCH 2 465 2-methoxyphenyl OCH 2 466 3-methoxyphenyl OCH 2 467 4-methoxyphenyl OCH 2 468 3,4-dimethoxyphenyl OCH 2 469 3,4,5-trimethoxyphenyl
OCH
2 470 2-ethoxyphenyl OCH 2 471 3-ethoxyphenyl OCH 2 472 4-ethoxyphenyl OCH 2 473 2-methoxy-3-(methylthio)phenyl OCH 2 474 2-nitrophenyl OCH 2 475 3-nitrophenyl OCH 2 476 4-nitrophenyl OCH 2 477 2-hydroxyphenyl OCH 2 478 3-hydroxyphenyl OCH 2 WO 2006/058730 PCT/EP2005/012787 42 A Q 479 4-hydroxyphenyl OCH 2 480 4-hydroxy-3-methoxyphenyl OCH 2 481 2-fluoro-4-hydroxyphenyl OCH 2 482 2-aminophenyl OCH 2 483 3-aminophenyl OCH 2 484 4-aminophenyl OCH 2 485 6-amino-2-fluorophenyl OCH 2 486 4-(dimethylamino)phenyl OCH 2 487 4-phenylphenyl OCH 2 488 4-(methylsulfonyl)-2-nitrophenyl OCH 2 489 5-methylpyrazin-2-yl OCH 2 490 3-aminopyrazin-2-yl OCH 2 491 2-furyl OCH 2 492 5-bromofuran-2-yl OCH 2 493 2-methylfuran-3-yl OCH 2 494 5-isoxazolyl OCH 2 495 3-methylisoxazolyl OCH 2 496 3-(1 -methylethyl)isoxazolyl OCH 2 497 5-(chloromethyl)isoxazolyl OCH 2 498 5-(hydroxymethyl)isoxazolyl OCH 2 499 1,3-bis( 1,1,1-trifluoroeth-2-yl)pyrazol-4-yl OCH 2 500 1 -methyl-3-(trifluoromethyl)pyrazol-5-yl OCH 2 501 3-methylimidazol-2-yl OCH 2 502 4-methylimididazol-5-yl OCH 2 503 4-amino-2-methylpyrimidin-2-yl OCH 2 504 6-hydroxy-2-methylpyrimidin-4-yl OCH 2 505 3-hydroxynapth-2-yl OCH 2 506 2-benzothienyl OCH 2 507 3-chloro-2-benzothienyl OCH 2 508 1 -naphthyl OCH 2 509 2-naphthyl OCH 2 510 3-indolyl OCH 2 511 2-benzimidazolyl OCH 2 512 6,7-dimethoxy-3-methyl-1,2,3,4- OCH 2 tetrahydroisochinolin-3-yl 513 2-thienyl OCH(CH 3 ) 514 3-bromothien-2-yl OCH(CH 3 ) 515 4-bromothien-2-yl OCH(CH 3
)
WO 2006/058730 PCT/EP2005/012787 43 A Q 516 5-bromothien-2-yl OCH(CH 3 ) 517 4,5-dibromthien-2-yl OCH(CH 3 ) 518 3-chlorothien-2-yl OCH(CH 3 ) 519 4-chlorothien-2-yl OCH(CH 3 ) 520 5-chlorothien-2-yl OCH(CH 3 ) 521 3-chloro-4-methylthien-2-yl OCH(CH 3 ) 522 3-methylthien-2-yl OCH(CH 3 ) 523 4-methylthien-2-yl OCH(CH 3 ) 524 5-methylthien-2-yl OCH(CH 3 ) 525 3-methoxythien-2-yl OCH(CH 3 ) 526 3-methoxy-5-(trifluoromethyl)thien-2-yl OCH(CH 3 ) 527 3-ethoxy-5-(trifluoromethyl)thien-2-yl OCH(CH 3 ) 528 2-bromo-4,5-dimethylthien-2-yl OCH(CH 3 ) 529 pyridin-2-yl OCH(CH 3 ) 530 6-methylthiopyridin-2-yl OCH(CH 3 ) 531 3-fluoropyridin-2-yl OCH(CH 3 ) 532 3-methoxypyridin-2-yl OCH(CH 3 ) 533 6-methylpyridin-2-yl OCH(CH 3 ) 534 5-nitropyridin-2-yl OCH(CH 3 ) 535 3-fluoropyridin-2-yl OCH(CH 3 ) 536 6-bromopyridin-2-yl OCH(CH 3 ) 537 6-chloropyridin-2-yl OCH(CH 3 ) 538 4-chloropyridin-2-yl OCH(CH 3 ) 539 3,6-dichloropyridin-2-yl OCH(CH 3 ) 540 6-fluoropyridin-2-yl OCH(CH 3 ) 541 5-(trifluoromethyl)pyridin-2-yl OCH(CH 3 ) 542 4-(trifluoromethyl)pyridin-2-yl OCH(CH 3 ) 543 6-(trifluoromethyl)pyridin-2-yl OCH(CH 3 ) 544 6-hydroxypyridin-2-yl OCH(CH 3 ) 545 6-methoxypyridin-2-yl OCH(CH 3 ) 546 3-hydroxypyridin-2-yl OCH(CH 3 ) 547 6-phenylpyridin-2-yl OCH(CH 3 ) 548 pyridin-3-yl OCH(CH 3 ) 549 6-chloropyridin-3-yl OCH(CH 3 ) 550 2,6-dichloropyridin-3-yl OCH(CH 3 ) 551 5,6-dichloropyridin-3-yl OCH(CH 3 ) 552 2,6-dichloro-4-methylpyridin-3-yl OCH(CH 3 ) 553 6-fluoropyridin-3-yl OCH(CH 3
)
WO 2006/058730 PCT/EP2005/012787 44 A Q 554 6-bromopyridin-3-yl
OCH(CH
3 ) 555 5-bromopyridin-3-yl OCH(CH 3 ) 556 2-phenoxypyridin-3-yl
OCH(CH
3 ) 557 1 -methyl-2-hydroxypyridin-3-yl OCH(CH 3 ) 558 pyridin-4-yl
OCH(CH
3 ) 559 2-chloropyridin-4-yl
OCH(CH
3 ) 560 2,6-dichloropyridin-4-yl
OCH(CH
3 ) 561 phenyl
OCH(CH
3 ) 562 2-fluorophenyl
OCH(CH
3 ) 563 3-fluorophenyl
OCH(CH
3 ) 564 4-fluorophenyl
OCH(CH
3 ) 565 2,4-difluorophenyl
OCH(CH
3 ) 566 2,5-difluorophenyl OCH(CHs) 567 2-chlorophenyl
OCH(CH
3 ) 568 3-chlorophenyl
OCH(CH
3 ) 569 4-chlorophenyl OCH(CHs) 570 2,3-dichlorophenyl
OCH(CH
3 ) 571 2,4-dichlorophenyl
OCH(CH
3 ) 572 2,5-dichlorophenyl
OCH(CH
3 ) 573 2,6-dichlorophenyl
OCH(CH
3 ) 574 2-chloro-6-fluorophenyl
OCH(CH
3 ) 575 2-chloro-4-fluorophenyl
OCH(CH
3 ) 576 1,2,3,4,5-pentafluorophenyl OCH(CHs) 577 2-bromophenyl
OCH(CH
3 ) 578 3-bromophenyl
OCH(CH
3 ) 579 4-bromophenyl
OCH(CH
3 ) 580 5-bromo-2-chlorophenyl
OCH(CH
3 ) 581 4-chloro-2-methylphenyl
OCH(CH
3 ) 582 3-fluoro-4-methylphenyl
OCH(CH
3 ) 583 2-methylphenyl
OCH(CH
3 ) 584 3-methylphenyl
OCH(CH
3 ) 585 4-methylphenyl
OCH(CH
3 ) 586 2,6-dimethylphenyl
OCH(CH
3 ) 587 2-(trifluoromethyl)phenyl
OCH(CH
3 ) 588 3-(trifluoromethyl)phenyl OCH(CHa) 589 4-(trifluoromethyl)phenyl
OCH(CH
3 ) 590 2-fluoro-4-(trifluoromethyl)phenyl
OCH(CH
3 ) 591 3,5-bis(trifluoromethyl)phenyl
OCH(CH
3
)
WO 2006/058730 PCT/EP2005/012787 45 A Q 592 4-tert.-butyl-phenyl OCH(CH 3 ) 593 2-methoxyphenyl OCH(CH 3 ) 594 3-methoxyphenyl OCH(CH 3 ) 595 4-methoxyphenyl OCH(CH 3 ) 596 3,4-dimethoxyphenyl OCH(CH 3 ) 597 3,4,5-trimethoxyphenyl OCH(CH 3 ) 598 2-ethoxyphenyl OCH(CH 3 ) 599 3-ethoxypheny) OCH(CH 3 ) 600 4-ethoxyphenyl OCH(CH 3 ) 601 2-methoxy-3-(methylthio)phenyl OCH(CH 3 ) 602 2-nitrophenyl OCH(CH 3 ) 603 3-nitrophenyl OCH(CH 3 ) 604 4-nitrophenyl OCH(CH 3 ) 605 2-hydroxyphenyl OCH(CH 3 ) 606 3-hydroxyphenyl OCH(CH 3 ) 607 4-hydroxyphenyl OCH(CH 3 ) 608 4-hydroxy-3-methoxyphenyl OCH(CH 3 ) 609 2-fluoro-4-hydroxyphenyl OCH(CH 3 ) 610 2-aminophenyl OCH(CH 3 ) 611 3-aminophenyl OCH(CH 3 ) 612 4-aminophenyl OCH(CH 3 ) 613 6-amino-2-fluorophenyl OCH(CH 3 ) 614 4-(dimethylamino)phenyl OCH(CHs) 615 4-phenylphenyl OCH(CH 3 ) 616 4-(methylsulfonyl)-2-nitropheny OCH(CH 3 ) 617 5-methylpyrazin-2-yl OCH(C H 3 ) 618 3-aminopyrazin-2-yl OCH(CH 3 ) 619 2-furyl OCH(CH 3 ) 620 5-bromofuran-2-yl OCH(CH 3 ) 621 2-methylfuran-3-yl OCH(CH 3 ) 622 5-isoxazolyl OCH(CH 3 ) 623 3-methylisoxazolyl OCH(CH 3 ) 624 3-(1 -methylethyl)isoxazolyl OCH(CH 3 ) 625 5-(chloromethyl)isoxazolyl OCH(CH 3 ) 626 5-(hydroxymethyl)isoxazolyl OCH(CH 3 ) 627 1,3-bis(1,1,1 -trifluoroeth-2-yl)pyrazol-4-yl OCH(CHs) 628 1-methyl-3-(trifluoromethyl)pyrazol-5-yl OCH(CHs) 629 3-methylimidazoi-2-yl OCH(CH 3
)
WO 2006/058730 PCT/EP2005/012787 46 A Q 630 4-methylimididazol-5-yl OCH(CH 3 ) 631 4-amino-2-methylpyrimidin-2-yl OCH(CH 3 ) 632 6-hydroxy-2-methylpyrimidin-4-yl OCH(CH 3 ) 633 3-hydroxynapth-2-yl OCH(CH 3 ) 634 2-benzothienyl OCH(CH 3 ) 635 3-chloro-2-benzothienyl
OCH(CH
3 ) 636 1-naphthyl OCH(CH 3 ) 637 2-naphthyl
OCH(CH
3 ) 638 3-indolyl OCH(CH 3 ) 639 2-benzimidazolyl
OCH(CH
3 ) 640 6,7-dimethoxy-3-methyl-1,2,3,4-
OCH(CH
3 ) tetrahydroisochinolin-3-yl 641 2-thienyl
SCH
2 642 3-bromothien-2-yl SCH 2 643 4-bromothien-2-yl SCH 2 644 5-bromothien-2-yl SCH 2 645 4,5-dibromthien-2-yl SCH 2 646 3-chlorothien-2-yl
SCH
2 647 4-chlorothien-2-yl
SCH
2 648 5-chlorothien-2-yl SCH 2 649 3-chloro-4-methylthien-2-yl
SCH
2 650 3-methylthien-2-yl SCH 2 651 4-methylthien-2-yl SCH 2 652 5-methylthien-2-yl SCH 2 653 3-methoxythien-2-yl SCH 2 654 3-methoxy-5-(trifluoromethyl)thien-2-yl
SCH
2 655 3-ethoxy-5-(trifluoromethyl)thien-2-yl SCH 2 656 2-bromo-4,5-dimethylthien-2-yl SCH 2 657 pyridin-2-yl SCH 2 658 6-methylthiopyridin-2-yl SCH 2 659 3-fluoropyridin-2-yl
SCH
2 660 3-methoxypyridin-2-yl SCH 2 661 6-methylpyridin-2-yl SCH 2 662 5-nitropyridin-2-yl SCH 2 663 3-fluoropyridin-2-yl SCH 2 664 6-bromopyridin-2-yl SCH 2 665 6-chloropyridin-2-yl SCH 2 666 4-chloropyridin-2-yl SCH 2 WO 2006/058730 PCT/EP2005/012787 47 A Q 667 3,6-dichloropyridin-2-yl SCH 2 668 6-fluoropyridin-2-yl SCH 2 669 5-(trifluoromethyl)pyridin-2-yl SCH 2 670 4-(trifluoromethyl)pyridin-2-yl SCH 2 671 6-(trifluoromethyl)pyridin-2-yl SCH 2 672 6-hydroxypyridin-2-yl SCH 2 673 6-methoxypyridin-2-yl SCH 2 674 3-hydroxypyridin-2-yl SCH 2 675 6-phenylpyridin-2-yl SCH 2 676 pyridin-3-yl SCH 2 677 6-chloropyridin-3-yl SCH 2 678 2,6-dichloropyridin-3-yl SCH 2 679 5,6-dichloropyridin-3-yl SCH 2 680 2,6-dichloro-4-methylpyridin-3-yl SCH 2 681 6-fluoropyridin-3-yl SCH 2 682 6-bromopyridin-3-yl SCH 2 683 5-bromopyridin-3-yl SCH 2 684 2-phenoxypyridin-3-yl SCH 2 685 1 -methyl-2-hydroxypyridin-3-yl SCH 2 686 pyridin-4-yl SCH 2 687 2-chloropyridin-4-yl SCH 2 688 2,6-dichloropyridin-4-yl SCH 2 689 phenyl SCH 2 690 2-fluorophenyl SCH 2 691 3-fluorophenyl SCH 2 692 4-fluorophenyl SCH 2 693 2,4-difluorophenyl SCH 2 694 2,5-difluorophenyl SCH 2 695 2-chlorophenyl SCH 2 696 3-chlorophenyl SCH 2 697 4-chlorophenyl SCH 2 698 2,3-dichlorophenyl SCH 2 699 2,4-dichlorophenyl SCH 2 700 2,5-dichlorophenyl SCH 2 701 2,6-dichlorophenyl SCH 2 702 2-chloro-6-fluorophenyl SCH 2 703 2-chloro-4-fluorophenyl SCH 2 704 1,2,3,4,5-pentafluorophenyl SCH 2 WO 2006/058730 PCT/EP2005/012787 48 A Q 705 2-bromophenyl SCH 2 706 3-bromophenyl SCH 2 707 4-bromophenyl SCH 2 708 5-bromo-2-chlorophenyl SCH 2 709 4-chloro-2-methylphenyl SCH 2 710 3-fluoro-4-methylphenyl SCH 2 711 2-methylphenyl SCH 2 712 3-methylphenyl SCH 2 713 4-methylphenyl SCH 2 714 2,6-dimethylphenyl SCH 2 715 2-(trifluoromethyl)phenyl SCH 2 716 3-(trifluoromethyl)phenyl SCH 2 717 4-(trifluoromethyl)phenyl SCH 2 718 2-fluoro-4-(trifluoromethyl)phenyl SCH 2 719 3,5-bis(trifluoromethyl)phenyl SCH 2 720 4-tert.-butyl-phenyl SCH 2 721 2-methoxyphenyl SCH 2 722 3-methoxyphenyl SCH 2 723 4-methoxyphenyl SCH 2 724 3,4-dimethoxyphenyl SCH 2 725 3,4,5-trimethoxyphenyl SCH 2 726 2-ethoxyphenyl SCH 2 727 3-ethoxyphenyl SCH 2 728 4-ethoxyphenyl SCH 2 729 2-methoxy-3-(methylthio)phenyl SCH 2 730 2-nitrophenyl SCH 2 731 3-nitrophenyl SCH 2 732 4-nitrophenyl SCH 2 733 2-hydroxyphenyl SCH 2 734 3-hydroxyphenyl SCH 2 735 4-hydroxyphenyl SCH 2 736 4-hydroxy-3-methoxyphenyl SCH 2 737 2-fluoro-4-hydroxyphenyl SCH 2 738 2-aminophenyl SCH 2 739 3-aminophenyl SCH 2 740 4-aminophenyl SCH 2 741 6-amino-2-fluorophenyl SCH 2 742 4-(dimethylamino)phenyl SCH 2 WO 2006/058730 PCT/EP2005/012787 49 A Q 743 4-phenylphenyl SCH 2 744 4-(methylsulfonyl)-2-nitrophenyl SCH 2 745 5-methylpyrazin-2-yl SCH 2 746 3-aminopyrazin-2-yl SCH 2 747 2-furyl SCH 2 748 5-bromofuran-2-yl SCH 2 749 2-methylfuran-3-yl SCH 2 750 5-isoxazolyl SCH 2 751 3-methylisoxazolyl SCH 2 752 3-(1 -methylethyl)isoxazolyl SCH 2 753 5-(chloromethyl)isoxazolyl SCH 2 754 5-(hydroxymethyl)isoxazolyl SCH 2 755 1,3-bis(1,,1 -trifluoroeth-2-yl)pyrazol-4-yl SCH 2 756 1 -methyl-3-(trifluoromethyl)pyrazol-5-yl SCH 2 757 3-methylimidazol-2-yl SCH 2 758 4-methylimididazol-5-yl SCH 2 759 4-amino-2-methylpyrimidin-2-yl SCH 2 760 6-hydroxy-2-methylpyrimidin-4-yl SCH 2 761 3-hydroxynapth-2-yl SCH 2 762 2-benzothienyl SCH 2 763 3-chloro-2-benzothienyl SCH 2 764 1-naphthyl SCH 2 765 2-naphthyl SCH 2 766 3-indolyl SCH 2 767 2-benzimidazolyl SCH 2 768 6,7-dimethoxy-3-methyl-1,2,3,4- SCH 2 tetrahydroisochinolin-3-yl 769 2-thienyl OCH 2
CH
2
CH
2 770 3-bromothien-2-yl OCH 2
CH
2
CH
2 771 4-bromothien-2-yl OCH 2
CH
2
CH
2 772 5-bromothien-2-yl OCH 2
CH
2
CH
2 773 4,5-dibromthien-2-yl OCH 2
CH
2
CH
2 774 3-chlorothien-2-yl OCH 2
CH
2
CH
2 775 4-chlorothien-2-yl OCH 2
CH
2
CH
2 776 5-chlorothien-2-yl OCH 2
CH
2
CH
2 777 3-chloro-4-methylthien-2-yl OCH 2
CH
2
CH
2 778 3-methylthien-2-yl OCH 2
CH
2
CH
2 779 4-methylthien-2-yl OCH 2
CH
2
CH
2 WO 2006/058730 PCT/EP2005/012787 50 A Q 780 5-methylthien-2-yi OCH 2
CH
2
CH
2 781 3-methoxythien-2-y OCH 2
CH
2
CH
2 782 3-methoxy-5-(trifluoromethyl)thien-2-yI OCH 2
CH
2
CH
2 783 3-ethoxy-5-(trifluoromethyl)thien-2-y OCH 2 C H 2 0H 2 784 2-bromo-4,5-dimethylthien-2-y OCH 2
CH
2
CH
2 785 pyridin-2-yi OCH 2
CH
2
CH
2 786 6-methylthiopyridin-2-y OCH 2
CH
2
CH
2 787 3-fluoropyridin-2-yl OCH 2
CH
2
CH
2 788 3-methoxypyrid in-2-yl OCH 2
CH
2
CH
2 789 6-methylpyrid in-2-yI OCH 2
CH
2
CH
2 790 5-nitropyridin-2-yI OCH 2
CH
2
CH
2 791 3-fluoropyridin-2-yi OCH 2
CH
2
CH
2 792 6-bromopyridin-2-yI OCH 2
CH
2
CH
2 793 6-chloropyridin-2-yI OCH 2
CH
2
CH
2 794 4-chioropyridin-2-y OCH 2
CH
2
CH
2 795 3,6-dichloropyridin-2-yI OCH 2
CH
2
CH
2 796 6-fl uoropyrid in-2-yI OCH 2
CH
2
CH
2 797 5-(trifluoromethyl)pyridin-2-y OCH 2
CH
2
CH
2 798 4-(trifluoromethyl)pyrid in-2-yi OCH 2
CH
2
CH
2 799 6-(trifluoromethyl)pyridin-2-yi OCH 2
CH
2
CH
2 800 6-hydroxypyridin-2-yI OCH 2
CH
2
CH
2 801 6-methoxypyridin-2-yI OCH 2
CH
2
CH
2 802 3-hydroxypyridin-2-yi OCH 2
CH
2
CH
2 803 6-phenylpyridin-2-yI OCH 2
CH
2
CH
2 804 pyridin-3-yI OCH 2
CH
2
CH
2 805 6-chloropyridin-3-yi OCH 2
CH
2
CH
2 806 2,6-dichloropyridin-3-yi OCH 2
CH
2
CH
2 807 5,6-dichloropyridin-3-y OCH 2
CH
2
CH
2 808 2,6-dichloro-4-methylpyridin-3-yl OCH 2
CH
2
CH
2 809 6-fluoropyridin-3-yl OCH 2
CH
2
CH
2 810 6-bromopyridin-3-y OCH 2
CH
2
CH
2 811 5-bromopyridin-3-yi OCH 2
CH
2
CH
2 812 2-phenoxypyridin-3-yi OCH 2
CH
2
CH
2 813 1 -methyl-2-hyd roxypyrid in-3-yI OCH 2
CH
2
CH
2 814 pyridin-4-yI OCH 2
CH
2
CH
2 815 2-chloropyridin-4-yl OCH 2
CH
2
CH
2 816 2,6-dichloropyridin-4-yI OCH 2
CH
2
CH
2 817 phenyl OCH 2
CH
2
CH
2 WO 2006/058730 PCT/EP2005/012787 51 A Q 818 2-fluorophenyl OCH 2
CH
2
CH
2 819 3-fluorophenyl OCH 2
CH
2
CH
2 820 4-fluorophenyl OCH 2
CH
2
CH
2 821 2,4-difluorophenyl OCH 2
CH
2
CH
2 822 2,5-difluorophenyl OCH 2
CH
2
CH
2 823 2-chlorophenyl OCH 2
CH
2
CH
2 824 3-chlorophenyl OCH 2
CH
2
CH
2 825 4-chlorophenyl OCH 2
CH
2
CH
2 826 2,3-dichlorophenyl OCH 2
CH
2
CH
2 827 2,4-dichlorophenyl OCH 2
CH
2
CH
2 828 2,5-dichlorophenyl OCH 2
CH
2
CH
2 829 2,6-dichlorophenyl OCH 2
CH
2
CH
2 830 2-chloro-6-fluorophenyl OCH 2
CH
2
CH
2 831 2-chloro-4-fluorophenyl OCH 2
CH
2
CH
2 832 1,2,3,4,5-pentafluorophenyl OCH 2
CH
2
CH
2 833 2-bromophenyl OCH 2
CH
2
CH
2 834 3-bromophenyl OCH 2
CH
2
CH
2 835 4-bromophenyl OCH 2
CH
2
CH
2 836 5-bromo-2-chlorophenyl OCH 2
CH
2
CH
2 837 4-chloro-2-methylphenyl OCH 2
CH
2
CH
2 838 3-fluoro-4-methylphenyl OCH 2
CH
2
CH
2 839 2-methylphenyl OCH 2
CH
2
CH
2 840 3-methylphenyl OCH 2
CH
2
CH
2 841 4-methylphenyl OCH 2
CH
2
CH
2 842 2,6-dimethylphenyl OCH 2
CH
2
CH
2 843 2-(trifluoromethyl)phenyl
OCH
2
CH
2
CH
2 844 3-(trifluoromethyl)phenyl OCH 2
CH
2
CH
2 845 4-(trifluoromethyl)phenyl OCH 2
CH
2
CH
2 846 2-fluoro-4-(trifluoromethyl)phenyl OCH 2
CH
2
CH
2 847 3,5-bis(trifluoromethyl)phenyl OCH 2
CH
2
CH
2 848 4-tert.-butyl-phenyl OCH 2
CH
2
CH
2 849 2-methoxyphenyl OCH 2
CH
2
CH
2 850 3-methoxyphenyl OCH 2
CH
2
CH
2 851 4-methoxyphenyl OCH 2
CH
2
CH
2 852 3,4-dimethoxyphenyl OCH 2
CH
2
CH
2 853 3,4,5-trimethoxyphenyl OCH 2
CH
2
CH
2 854 2-ethoxyphenyl OCH 2
CH
2
CH
2 855 3-ethoxyphenyl OCH 2
CH
2
CH
2 WO 2006/058730 PCT/EP2005/012787 52 A Q 856 4-ethoxyphenyl
OCH
2
CH
2
CH
2 857 2-methoxy-3-(methylthio)phenyl
OCH
2
CH
2
CH
2 858 2-nitrophenyl
OCH
2
CH
2
CH
2 859 3-nitrophenyl
OCH
2
CH
2
CH
2 860 4-nitrophenyl
OCH
2
CH
2
CH
2 861 2-hydroxyphenyl
OCH
2
CH
2
CH
2 862 3-hydroxyphenyl
OCH
2
CH
2
CH
2 863 4-hydroxyphenyl
OCH
2
CH
2
CH
2 864 4-hydroxy-3-methoxyphenyl
OCH
2
CH
2 CH2 865 2-fluoro-4-hydroxyphenyl
OCH
2
CH
2
CH
2 866 2-aminophenyl
OCH
2
CH
2
CH
2 867 3-aminophenyl
OCH
2
CH
2
CH
2 868 4-aminophenyl
OCH
2
CH
2
CH
2 869 6-amino-2-fluorophenyl
OCH
2
CH
2
CH
2 870 4-(dimethylamino)phenyl
OCH
2
CH
2
CH
2 871 4-phenylphenyl
OCH
2
CH
2
CH
2 872 4-(methylsulfonyl)-2-nitrophenyl
OCH
2
CH
2
CH
2 873 5-methylpyrazin-2-yl
OCH
2
CH
2
CH
2 874 3-aminopyrazin-2-yl
OCH
2
CH
2
CH
2 875 2-furyl
OCH
2
CH
2
CH
2 876 5-bromofuran-2-yl
OCH
2
CH
2
CH
2 877 2-methylfuran-3-yl
OCH
2
CH
2
CH
2 878 5-isoxazolyl
OCH
2
CH
2
CH
2 879 3-methylisoxazolyl
OCH
2
CH
2
CH
2 880 3-(1 -methylethyl)isoxazolyl
OCH
2
CH
2
CH
2 881 5-(chloromethyl)isoxazolyl
OCH
2
CH
2
CH
2 882 5-(hydroxymethyl)isoxazolyl
OCH
2
CH
2
CH
2 883 1,3-bis(1,1,1 -trifluoroeth-2-yl)pyrazol-4-yl
OCH
2
CH
2
CH
2 884 1-methyl-3-(trifluoromethyl)pyrazol-5-yl
OCH
2
CH
2
CH
2 885 3-methylimidazol-2-yl
OCH
2
CH
2
CH
2 886 4-methylimididazol-5-yl
OCH
2
CH
2
CH
2 887 4-amino-2-methylpyrimidin- 2 -yl OCH 2
CH
2
CH
2 888 6-hydroxy-2-methylpyrimidin-4-yl
OCH
2
CH
2
CH
2 889 3-hydroxynapth-2-yl
OCH
2
CH
2
CH
2 890 2-benzothienyl
OCH
2
CH
2
CH
2 891 3-chloro-2-benzothienyl
OCH
2
CH
2
CH
2 892 1-naphthyl
OCH
2
CH
2
CH
2 893 2-naphthyl
OCH
2
CH
2
CH
2 WO 2006/058730 53PCT/EP2005/012787 A Q 894 3-indolyl OCH 2
CH
2
CH
2 895 2-benzimidazolyl OCH 2
CH
2
CH
2 896 6,7-dimethoxy-3-methyl-1 ,2,3,4- OCH 2
CH
2
CH
2 tetrahyd roisochinolin-3-yi__________ 897 2-thienyl NHCH 2
CH
2 898 3-bromothien-2-yl NHCH 2
CH
2 899 4-bromothien-2-yi NHCH 2
CH
2 900 5-bromothien-2-yI NHCH 2
CH
2 901 4,5-dibromthien-2-yI NHCH 2
CH
2 902 3-chlorothien-2-yI NHCH 2
CH
2 903 4-chlorothien-2-yl N HCH 2
CH
2 904 5-chlorothien-2-yI NHCH 2
CH
2 905 3-chloro-4-methylthien-2-yI NHCH 2
CH
2 906 3-methylthien-2-yi NHCH 2
CH
2 907 4-methylthien-2-yi NHCH 2
CH
2 908 5-methylthien-2-yi NHCH 2
CH
2 909 3-methoxythien-2-yi N HCH 2
CH
2 910 3-methoxy-5-(trifluoromethyl)thien-2-yI N HCH 2
CH
2 911 3-ethoxy-5-(trifluoromethyl)thien-2-yI N HCH 2
CH
2 912 2-bromo-4,5-dimethylthien-2-yI NHCH 2
CH
2 913 pyridin-2-yl NHCH 2
CH
2 914 6-methyithiopyridin-2-y NHCH 2
CH
2 915 3-fluoropyridin-2-yI NHCH 2
CH
2 916 3-methoxypyridin-2-yi NHCH 2
CH
2 917 6-methylpyridin-2-y! NHCH 2
CH
2 918 5-n itropyrid in-2-yI N HCH 2
CH
2 919 3-fluoropyridin-2-yl NHCH 2
CH
2 920 6-bromopyridin-2-yi NHCH 2
CH
2 921 6-chloropyrid in-2-yI N HCH 2
CH
2 922 4-chloropyridin-2-yI NHCH 2
CH
2 923 3,6-dichloropyridin-2-yI NHCH 2
CH
2 924 6-fluoropyridin-2-yi NHCH 2
CH
2 925 5-(trifluoromethyl)pyrid in-2-yI N HCH 2
CH
2 926 4-(trifluoromethyl)pyridin-2-yi NHCH 2
CH
2 927 6-(trifluoromethyi)pyridin-2-yi N HCH 2 C H 2 928 6-hydroxypyrid in-2-yI N HCH 2
CH
2 929 6-methoxypyrid in-2-yI N HCH 2
CH
2 930 3-hydroxypyridin-2-yI NHCH 2
CH
2 WO 2006/058730 PCT/EP2005/012787 54 A Q 931 6-phenylpyridin-2-yl NHCH 2
CH
2 932 pyridin-3-yl NHCH 2
CH
2 933 6-chloropyridin-3-yl NHCH 2
CH
2 934 2,6-dichloropyridin-3-yl NHCH 2
CH
2 935 5,6-dichloropyridin-3-yl NHCH 2
CH
2 936 2,6-dichloro-4-methylpyridin-3-yl NHCH 2
CH
2 937 6-fluoropyridin-3-yl NHCH 2
CH
2 938 6-bromopyridin-3-yl NHCH 2
CH
2 939 5-bromopyridin-3-yl NHCH 2
CH
2 940 2-phenoxypyridin-3-yl NHCH 2
CH
2 941 1-methyl-2-hydroxypyridin-3-yl NHCH 2
CH
2 942 pyridin-4-yl NHCH 2
CH
2 943 2-chloropyridin-4-yl NHCH 2
CH
2 944 2,6-dichloropyridin-4-yl NHCH 2
CH
2 945 phenyl NHCH 2
CH
2 946 2-fluorophenyl NHCH 2
CH
2 947 3-fluorophenyl NHCH 2
CH
2 948 4-fluorophenyl NHCH 2
CH
2 949 2,4-difluorophenyl NHCH 2
CH
2 950 2,5-difluorophenyl NHCH 2
CH
2 951 2-chlorophenyl NHCH 2
CH
2 952 3-chlorophenyl NHCH 2
CH
2 953 4-chlorophenyl NHCH 2
CH
2 954 2,3-dichlorophenyl NHCH 2
CH
2 955 2,4-dichlorophenyl NHCH 2
CH
2 956 2,5-dichlorophenyl NHCH 2
CH
2 957 2,6-dichlorophenyl NHCH 2
CH
2 958 2-chloro-6-fluorophenyl NHCH 2
CH
2 959 2-chloro-4-fluorophenyl NHCH 2
CH
2 960 1,2,3,4,5-pentafluorophenyl NHCH 2
CH
2 961 2-bromophenyl NHCH 2
CH
2 962 3-bromophenyl NHCH 2
CH
2 963 4-bromophenyl NHCH 2
CH
2 964 5-bromo-2-chlorophenyl NHCH 2
CH
2 965 4-chloro-2-methylphenyl NHCH 2
CH
2 966 3-fluoro-4-methylphenyl NHCH 2
CH
2 967 2-methylphenyl NHCH 2
CH
2 968 3-methylphenyl NHCH 2
CH
2 WO 2006/058730 PCT/EP2005/012787 55 A Q 969 4-methylphenyl NHCH 2
CH
2 970 2,6-dimethylphenyl NHCH 2
CH
2 971 2-(trifluoromethyl)phenyl NHCH 2
CH
2 972 3-(trifluoromethyl)phenyl NHCH 2
CH
2 973 4-(trifluoromethyl)phenyl NHCH 2
CH
2 974 2-fluoro-4-(trifluoromethyl)phenyl NHCH 2
CH
2 975 3,5-bis(trifluoromethyl)phenyl NHCH 2
CH
2 976 4-tert.-butyl-phenyl NHCH 2
CH
2 977 2-methoxyphenyl NHCH 2
CH
2 978 3-methoxyphenyl NHCH 2
CH
2 979 4-methoxyphenyl NHCH 2
CH
2 980 3,4-dimethoxyphenyl NHCH 2
CH
2 981 3,4,5-trimethoxyphenyl NHCH 2
CH
2 982 2-ethoxyphenyl NHCH 2
CH
2 983 3-ethoxyphenyl NHCH 2
CH
2 984 4-ethoxyphenyl NHCH 2
CH
2 985 2-methoxy-3-(methylthio)phenyl
NHCH
2
CH
2 986 2-nitrophenyl NHCH 2
CH
2 987 3-nitrophenyl NHCH 2
CH
2 988 4-nitrophenyl NHCH 2
CH
2 989 2-hydroxyphenyl NHCH 2
CH
2 990 3-hydroxyphenyl NHCH 2
CH
2 991 4-hydroxyphenyl NHCH 2
CH
2 992 4-hydroxy-3-methoxyphenyl NHCH 2
CH
2 993 2-fluoro-4-hydroxyphenyl NHCH 2
CH
2 994 2-aminophenyl NHCH 2
CH
2 995 3-aminophenyl NHCH 2
CH
2 996 4-aminophenyl NHCH 2
CH
2 997 6-amino-2-fluorophenyl NHCH 2
CH
2 998 4-(dimethylamino)phenyl NHCH 2
CH
2 999 4-phenylphenyl NHCH 2
CH
2 1000 4-(methylsulfonyl)-2-nitrophenyl NHCH 2
CH
2 1001 5-methylpyrazin-2-yl NHCH 2
CH
2 1002 3-aminopyrazin-2-yl NHCH 2
CH
2 1003 2-furyl NHCH 2
CH
2 1004 5-bromofuran-2-yl NHCH 2
CH
2 1005 2-methylfuran-3-yl NHCH 2
CH
2 1006 5-isoxazolyl NHCH 2
CH
2 WO 2006/058730 PCT/EP2005/012787 56 A Q 1007 3-methylisoxazolyl NHCH 2
CH
2 1008 3-(1-methylethyl)isoxazolyl NHCH 2
CH
2 1009 5-(chloromethyl)isoxazolyl NHCH 2
CH
2 1010 5-(hydroxymethyl)isoxazolyl NHCH 2
CH
2 1011 1,3-bis(1,1,1 -trifluoroeth-2-yl)pyrazol-4-yl NHCH 2
CH
2 1012 1-methyl-3-(trifluoromethyl)pyrazol-5-yl NHCH 2
CH
2 1013 3-methylimidazol-2-yl NHCH 2
CH
2 1014 4-methylimididazol-5-yl NHCH 2
CH
2 1015 4-amino-2-methylpyrimidin-2-yl NHCH 2
CH
2 1016 6-hydroxy-2-methylpyrimidin-4-yl NHCH 2
CH
2 1017 3-hydroxynapth-2-yl NHCH 2
CH
2 1018 2-benzothienyl NHCH 2
CH
2 1019 3-chloro-2-benzothienyl NHCH 2
CH
2 1020 1-naphthyl NHCH 2
CH
2 1021 2-naphthyl NHCH 2
CH
2 1022 3-indolyl NHCH 2
CH
2 1023 2-benzimidazolyl NHCH 2
CH
2 1024 6,7-dimethoxy-3-methyl-1,2,3,4- NHCH 2
CH
2 tetrahydroisochinolin-3-yl 1025 2-thienyl NHC(O)CH 2 1026 3-bromothien-2-yl NHC(O)CH 2 1027 4-bromothien-2-yl NHC(O)CH 2 1028 5-bromothien-2-yl NHC(O)CH 2 1029 4,5-dibromthien-2-yl NHC(O)CH 2 1030 3-chlorothien-2-yl NHC(O)CH 2 1031 4-chlorothien-2-yl NHC(O)CH 2 1032 5-chlorothien-2-yl NHC(O)CH 2 1033 3-chloro-4-methylthien-2-yl NHC(O)CH 2 1034 3-methylthien-2-yl NHC(O)CH 2 1035 4-methylthien-2-yl NHC(O)CH 2 1036 5-methylthien-2-yl NHC(O)CH 2 1037 3-methoxythien-2-yl NHC(O)CH 2 1038 3-methoxy-5-(trifluoromethyl)thien-2-yl NHC(O)CH 2 1039 3-ethoxy-5-(trifluoromethyl)thien-2-yl NHC(O)CH 2 1040 2-bromo-4,5-dimethylthien-2-yl NHC(O)CH 2 1041 pyridin-2-yl NHC(O)CH 2 1042 6-methylthiopyridin-2-yl NHC(O)CH 2 1043 3-fluoropyridin-2-yl NHC(O)CH 2 WO 2006/058730 PCT/EP2005/012787 57 A Q 1044 3-methoxypyridin-2-yl NHC(O)CH 2 1045 6-methylpyridin-2-yl NHC(O)CH 2 1046 5-nitropyridin-2-yl NHC(O)CH 2 1047 3-fluoropyridin-2-yl NHC(O)CH 2 1048 6-bromopyridin-2-yl NHC(O)CH 2 1049 6-chloropyridin-2-yl NHC(O)CH 2 1050 4-chloropyridin-2-yl NHC(O)CH 2 1051 3,6-dichloropyridin-2-yl NHC(O)CH 2 1052 6-fluoropyridin-2-yl NHC(O)CH 2 1053 5-(trifluoromethyl)pyridin-2-yl NHC(O)CH 2 1054 4-(trifluoromethyl)pyridin-2-yl NHC(O)CH 2 1055 6-(trifluoromethyl)pyridin-2-yl NHC(O)CH 2 1056 6-hydroxypyridin-2-yl NHC(O)CH 2 1057 6-methoxypyridin-2-yl NHC(O)CH 2 1058 3-hydroxypyridin-2-yl NHC(O)CH 2 1059 6-phenylpyridin-2-yl NHC(O)CH 2 1060 pyridin-3-yl NHC(O)CH 2 1061 6-chloropyridin-3-yl NHC(O)CH 2 1062 2,6-dichloropyridin-3-yl NHC(O)CH 2 1063 5,6-dichloropyridin-3-yl NHC(O)CH 2 1064 2,6-dichloro-4-methylpyridin-3-yl NHC(O)CH 2 1065 6-fluoropyridin-3-yl NHC(O)CH 2 1066 6-bromopyridin-3-yl NHC(O)CH 2 1067 5-bromopyridin-3-yl NHC(O)CH 2 1068 2-phenoxypyridin-3-yl NHC(O)CH 2 1069 1 -methyl-2-hydroxypyridin-3-yl NHC(O)CH 2 1070 pyridin-4-yl NHC(O)CH 2 1071 2-chloropyridin-4-yl NHC(O)CH 2 1072 2,6-dichloropyridin-4-yl NHC(O)CH 2 1073 phenyl NHC(O)CH 2 1074 2-fluorophenyl NHC(O)CH 2 1075 3-fluorophenyl NHC(O)CH 2 1076 4-fluorophenyl NHC(O)CH 2 1077 2,4-difluorophenyl NHC(O)CH 2 1078 2,5-difluorophenyl NHC(O)CH 2 1079 2-chlorophenyl NHC(O)CH 2 1080 3-chlorophenyl NHC(O)CH 2 1081 4-chlorophenyl NHC(O)CH 2 WO 2006/058730 PCT/EP2005/012787 58 A Q 1082 2,3-dichlorophenyl NHC(O)CH 2 1083 2,4-dichlorophenyl NHC(O)CH 2 1084 2,5-dichlorophenyl NHC(O)CH 2 1085 2,6-dichlorophenyl NHC(O)CH 2 1086 2-chloro-6-fluorophenyl NHC(O)CH 2 1087 2-chloro-4-fluorophenyl NHC(O)CH 2 1088 1,2,3,4,5-pentafluorophenyl NHC(O)CH 2 1089 2-bromophenyl NHC(O)CH 2 1090 3-bromophenyl NHC(O)CH 2 1091 4-bromophenyl NHC(O)CH 2 1092 5-bromo-2-chlorophenyl NHC(O)CH 2 1093 4-chloro-2-methylphenyl NHC(O)CH 2 1094 3-fluoro-4-methylphenyl NHC(O)CH 2 1095 2-methylphenyl NHC(O)CH 2 1096 3-methylphenyl NHC(O)CH 2 1097 4-methylphenyl NHC(O)CH 2 1098 2,6-dimethylphenyl NHC(O)CH 2 1099 2-(trifluoromethyl)phenyl NHC(O)CH 2 1100 3-(trifluoromethyl)phenyl NHC(O)CH 2 1101 4-(trifluoromethyl)phenyl NHC(O)CH 2 1102 2-fluoro-4-(trifluoromethyl)phenyl NHC(O)CH 2 1103 3,5-bis(trifluoromethyl)phenyl NHC(O)CH 2 1104 4-tert.-butyl-phenyl NHC(O)CH 2 1105 2-methoxyphenyl NHC(O)CH 2 1106 3-methoxyphenyl NHC(O)CH 2 1107 4-methoxyphenyl NHC(O)CH 2 1108 3,4-dimethoxyphenyl NHC(O)CH 2 1109 3,4,5-trimethoxyphenyl NHC(O)CH 2 1110 2-ethoxyphenyl NHC(O)CH 2 1111 3-ethoxyphenyl NHC(O)CH 2 1112 4-ethoxyphenyl NHC(O)CH 2 1113 2-methoxy-3-(methylthio)phenyl NHC(O)CH 2 1114 2-nitrophenyl NHC(O)CH 2 1115 3-nitrophenyl NHC(O)CH 2 1116 4-nitrophenyl NHC(O)CH 2 1117 2-hydroxyphenyl NHC(O)CH 2 1118 3-hydroxyphenyl NHC(O)CH 2 1119 4-hydroxyphenyl NHC(O)CH 2 WO 2006/058730 PCT/EP2005/012787 59 A Q 1120 4-hydroxy-3-methoxyphenyl NHC(O)CH 2 1121 2-fluoro-4-hydroxyphenyl NHC(O)CH 2 1122 2-aminophenyl NHC(O)CH 2 1123 3-aminophenyl NHC(O)CH 2 1124 4-aminophenyl NHC(O)CH 2 1125 6-amino-2-fluorophenyl NHC(O)CH 2 1126 4-(dimethylamino)phenyl NHC(O)CH 2 1127 4-phenylphenyl NHC(O)CH 2 1128 4-(methylsulfonyl)-2-nitrophenyl NHC(O)CH 2 1129 5-methylpyrazin-2-yl NHC(O)CH 2 1130 3-aminopyrazin-2-yl NHC(O)CH 2 1131 2-furyl NHC(O)CH 2 1132 5-bromofuran-2-yl NHC(O)CH 2 1133 2-methylfuran-3-yl NHC(O)CH 2 1134 5-isoxazolyl NHC(O)CH 2 1135 3-methylisoxazolyl NHC(O)CH 2 1136 3-(1-methylethyl)isoxazolyl NHC(O)CH 2 1137 5-(chloromethyl)isoxazolyl NHC(O)CH 2 1138 5-(hydroxymethyl)isoxazolyl NHC(O)CH 2 1139 1,3-bis( 1,,1 -trifluoroeth-2-yl)pyrazol-4-yl NHC(O)CH 2 1140 1-methyl-3-(trifluoromethyl)pyrazol-5-yl NHC(O)CH 2 1141 3-methylimidazol-2-yl NHC(O)CH 2 1142 4-methylimididazol-5-yl NHC(O)CH 2 1143 4-amino-2-methylpyrimidin-2-yl NHC(O)CH 2 1144 6-hydroxy-2-methylpyrimidin-4-yl NHC(O)CH 2 1145 3-hydroxynapth-2-yl NHC(O)CH 2 1146 2-benzothienyl NHC(O)CH 2 1147 3-chloro-2-benzothienyl NHC(O)CH 2 1148 1-naphthyl NHC(O)CH 2 1149 2-naphthyl NHC(O)CH 2 1150 3-indolyl NHC(O)CH 2 1151 2-benzimidazolyl NHC(O)CH 2 1152 6,7-dimethoxy-3-methyl-1,2,3,4- NHC(O)CH 2 tetrahydroisochinolin-3-yl 1153 2-thienyl SCH(CH 3 ) 1154 3-bromothien-2-yl SCH(CH 3 ) 1155 4-bromothien-2-yl SCH(CH 3 ) 1156 5-bromothien-2-yl SCH(CH 3
)
WO 2006/058730 PCT/EP2005/012787 60 A Q 1157 4,5-dibromthien-2-yl SCH(CHa) 1158 3-chlorothien-2-yl
SCH(CH
3 ) 1159 4-chlorothien-2-yl
SCH(CH
3 ) 1160 5-chlorothien-2-yl
SCH(CH
3 ) 1161 3-chloro-4-methylthien-2-yl
SCH(CH
3 ) 1162 3-methylthien-2-yl
SCH(CH
3 ) 1163 4-methylthien-2-yl
SCH(CH
3 ) 1164 5-methylthien-2-yl
SCH(CH
3 ) 1165 3-methoxythien-2-yl
SCH(CH
3 ) 1166 3-methoxy-5-(trifluoromethyl)thien-2-yl
SCH(CH
3 ) 1167 3-ethoxy-5-(trifluoromethyl)thien-2-yl
SCH(CH
3 ) 1168 2-bromo-4,5-dimethylthien-2-yl
SCH(CH
3 ) 1169 pyridin-2-yl
SCH(CH
3 ) 1170 6-methylthiopyridin-2-yl
SCH(CH
3 ) 1171 3-fluoropyridin-2-yl
SCH(CH
3 ) 1172 3-methoxypyridin-2-yl
SCH(CH
3 ) 1173 6-methylpyridin-2-yl
SCH(CH
3 ) 1174 5-nitropyridin-2-yl
SCH(CH
3 ) 1175 3-fluoropyridin-2-yl
SCH(CH
3 ) 1176 6-bromopyridin-2-yl
SCH(CH
3 ) 1177 6-chloropyridin-2-yl
SCH(CH
3 ) 1178 4-chloropyridin-2-yl
SCH(CH
3 ) 1179 3,6-dichloropyridin-2-yl
SCH(CH
3 ) 1180 6-fluoropyridin-2-yl
SCH(CH
3 ) 1181 5-(trifluoromethyl)pyridin-2-yl
SCH(CH
3 ) 1182 4-(trifluoromethyl)pyridin-2-yl
SCH(CH
3 ) 1183 6-(trifluoromethyl)pyridin-2-yl
SCH(CH
3 ) 1184 6-hydroxypyridin-2-yl
SCH(CH
3 ) 1185 6-methoxypyridin-2-yl
SCH(CH
3 ) 1186 3-hydroxypyridin-2-yl
SCH(CH
3 ) 1187 6-phenylpyridin-2-yl
SCH(CH
3 ) 1188 pyridin-3-yl
SCH(CH
3 ) 1189 6-chloropyridin-3-yl
SCH(CH
3 ) 1190 2,6-dichloropyridin-3-yl
SCH(CH
3 ) 1191 5,6-dichloropyridin-3-yl
SCH(CH
3 ) 1192 2,6-dichloro-4-methylpyridin-3-yl
SCH(CH
3 ) 1193 6-fluoropyridin-3-yl SCH(CH3) 1194 6-bromopyridin-3-yl
SCH(CH
3
)
WO 2006/058730 PCT/EP2005/012787 61 A Q 1195 5-bromopyridin-3-yl
SCH(CH
3 ) 1196 2-phenoxypyridin-3-yl
SCH(CH
3 ) 1197 1-methyl-2-hydroxypyridin-3-yl
SCH(CH
3 ) 1198 pyridin-4-yl
SCH(CH
3 ) 1199 2-chloropyridin-4-yl
SCH(CH
3 ) 1200 2,6-dichloropyridin-4-yl
SCH(CH
3 ) 1201 phenyl
SCH(CH
3 ) 1202 2-fluorophenyl
SCH(CH
3 ) 1203 3-fluorophenyl
SCH(CH
3 ) 1204 4-fluorophenyl
SCH(CH
3 ) 1205 2,4-difluorophenyl
SCH(CH
3 ) 1206 2,5-difluorophenyl
SCH(CH
3 ) 1207 2-chlorophenyl
SCH(CH
3 ) 1208 3-chlorophenyl
SCH(CH
3 ) 1209 4-chlorophenyl
SCH(CH
3 ) 1210 2,3-dichlorophenyl
SCH(CH
3 ) 1211 2,4-dichlorophenyl
SCH(CH
3 ) 1212 2,5-dichlorophenyl
SCH(CH
3 ) 1213 2,6-dichlorophenyl
SCH(CH
3 ) 1214 2-chloro-6-fluorophenyl
SCH(CH
3 ) 1215 2-chloro-4-fluorophenyl
SCH(CH
3 ) 1216 1,2,3,4,5-pentafluorophenyl
SCH(CH
3 ) 1217 2-bromophenyl
SCH(CH
3 ) 1218 3-bromophenyl
SCH(CH
3 ) 1219 4-bromophenyl
SCH(CH
3 ) 1220 5-bromo-2-chlorophenyl
SCH(CH
3 ) 1221 4-chloro-2-methylphenyl
SCH(CH
3 ) 1222 3-fluoro-4-methylphenyl
SCH(CH
3 ) 1223 2-methylphenyl
SCH(CH
3 ) 1224 3-methylphenyl
SCH(CH
3 ) 1225 4-methylphenyl
SCH(CH
3 ) 1226 2,6-dimethylphenyl
SCH(CH
3 ) 1227 2-(trifluoromethyl)phenyl
SCH(CH
3 ) 1228 3-(trifluoromethyl)phenyl
SCH(CH
3 ) 1229 4-(trifluoromethyl)phenyl
SCH(CH
3 ) 1230 2-fluoro-4-(trifluoromethyl)phenyl
SCH(CH
3 ) 1231 3,5-bis(trifluoromethyl)phenyl
SCH(CH
3 ) 1232 4-tert.-butyl-phenyl
SCH(CH
3
)
WO 2006/058730 PCT/EP2005/012787 62 A Q 1233 2-methoxyphenyl
SCH(CH
3 ) 1234 3-methoxyphenyl
SCH(CH
3 ) 1235 4-methoxyphenyl
SCH(CH
3 ) 1236 3,4-dimethoxyphenyl
SCH(CH
3 ) 1237 3,4,5-trimethoxyphenyl
SCH(CH
3 ) 1238 2-ethoxyphenyl
SCH(CH
3 ) 1239 3-ethoxyphenyl
SCH(CH
3 ) 1240 4-ethoxyphenyl
SCH(CH
3 ) 1241 2-methoxy-3-(methylthio)phenyl
SCH(CH
3 ) 1242 2-nitrophenyl SCH(CH) 1243 3-nitrophenyl
SCH(CH
3 ) 1244 4-nitrophenyl
SCH(CH
3 ) 1245 2-hydroxyphenyl
SCH(CH
3 ) 1246 3-hydroxyphenyl
SCH(CH
3 ) 1247 4-hydroxyphenyl
SCH(CH
3 ) 1248 4-hydroxy-3-methoxyphenyl
SCH(CH
3 ) 1249 2-fluoro-4-hydroxyphenyl
SCH(CH
3 ) 1250 2-aminophenyl
SCH(CH
3 ) 1251 3-aminophenyl
SCH(CH
3 ) 1252 4-aminophenyl
SCH(CH
3 ) 1253 6-amino-2-fluorophenyl
SCH(CH
3 ) 1254 4-(dimethylamino)phenyl
SCH(CH
3 ) 1255 4-phenylphenyl
SCH(CH
3 ) 1256 4-(methylsulfonyl)-2-nitrophenyl
SCH(CH
3 ) 1257 5-methylpyrazin-2-yl
SCH(CH
3 ) 1258 3-aminopyrazin-2-yl SCH(CH3) 1259 2-furyl
SCH(CH
3 ) 1260 5-bromofuran-2-yl
SCH(CH
3 ) 1261 2-methylfuran-3-yl
SCH(CH
3 ) 1262 5-isoxazolyl
SCH(CH
3 ) 1263 3-methylisoxazolyl
SCH(CH
3 ) 1264 3-(1 -methylethyl)isoxazolyl SCH(CH3) 1265 5-(chloromethyl)isoxazolyl
SCH(CH
3 ) 1266 5-(hydroxymethyl)isoxazolyl
SCH(CH
3 ) 1267 1,3-bis(1, 1,1 -trifluoroeth-2-yl)pyrazol-4-yl SCH(CH 3 ) 1268 1-methyl-3-(trifluoromethyl)pyrazol-5-yl
SCH(CH
3 ) 1269 3-methylimidazol-2-yl
SCH(CH
3 ) 1270 4-methylimididazol-5-yl
SCH(CH
3
)
WO 2006/058730 PCT/EP2005/012787 63 A Q 1271 4-amino-2-methylpyrimidin-2-yl
SCH(CH
3 ) 1272 6-hydroxy-2-methylpyrimidin-4-yl
SCH(CH
3 ) 1273 3-hydroxynapth-2-yl
SCH(CH
3 ) 1274 2-benzothienyl
SCH(CH
3 ) 1275 3-chloro-2-benzothienyl
SCH(CH
3 ) 1276 1-naphthyl
SCH(CH
3 ) 1277 2-naphthyl
SCH(CH
3 ) 1278 3-indolyl
SCH(CH
3 ) 1279 2-benzimidazolyl
SCH(CH
3 ) 1280 6,7-dimethoxy-3-methyl-1,2,3,4-
SCH(CH
3 ) tetrahydroisochinolin-3-yl 1281
CH
3 1282
CH
2
CH
3 1283
CH
2
CH
2
CH
3 1284 CH 2
CH
2
CH
2
CH
3 1285
CH
2
-(CH
2
)
3
-CH
3 1286
CH
2
-(CH
2
)
4
-CH
3 1287
CH
2
-(CH
2
)
5
-CH
3 1288
CH
2
-(CH
2
)
6
-CH
3 1289
CH
2
CO
2
CH
3 1290
CH
2 CO2C 2
H
5 1291
CH
2
(CH
2
)
3 0H 1292
CH
2
(CH
2
)
4 0H 1293 CH 2
CH(OCH
3
)
2 1294 CH 2
CH(OC
2
H
5
)
2 In table A the heteroatom of the moiety Q is attached to the radical A. Another very preferred embodiment of the invention relates to compounds of the 5 general formula la': O R R 2 1 I I (RC)k (la') All Q J N \ 15 1 3 R R R WO 2006/058730 PCT/EP2005/012787 64 wherein k is 0, 1, 2 or 3, and wherein A, Q, R 1 , R 2 , R 3 , R 5 , R 6 and Rc are as defined above. Amongst the compounds la' those are preferred, wherein Q, A, R 1 , R 2 , R 3 , R 5 ,
R
6 and Rc have the meanings given as preferred. 5 Examples of compounds la' are given in the following tables 181 to 360: Tables 181 to 270: Compounds of the formula la', wherein R 1 is H, R 3 is H, R 2 is H, R 5 is H, R 6 is CH 3 and (RC)k are as defined in one of the tables 1 to 90 and Q and A are given in table A. 10 Tables 271 to 360: Compounds of the formula la', wherein R 1 is H, R 3 is H, R 2 is H, R 5 is CH 3 , R 6 is CH 3 and (Rc)k are as defined in one of the tables 1 to 90 and Q and A are given in table A. 15 Another very preferred embodiment of the invention relates to compounds of the general formula Ib: A II H (R), (Ib) 15 1 3 R R R 20 wherein k is 0, 1, 2 or 3, and wherein A, Q, R 1 , R 3 , R6 and Rc are as defined above and Y is as defined above. Amongst the compounds la those are preferred, wherein Y is O,
OCH
2 or S and wherein Q, A, R 1 , R 3 , R 5 and Rc have the meanings given as preferred. 25 Examples of compounds Ib are given in the following tables 361 to 378: Table 361: Compounds of the formula la, wherein Y is O, R 1 is H, R 3 is H, R 5 is H and k is 0 (i.e. (Rc)k is absent) and wherein Q and A are given in table A; 30 Table 362: Compounds of the formula la, wherein Y is O, R 1 is H, R 3 is H, R 5 is CH 3 and k is 0 (i.e. (RC)k is absent) and wherein Q and A are given in table A; 35 Table 363: Compounds of the formula la, wherein Y is S, R 1 is H, R 3 is H, R 5 is H and k is 0 (i.e. (RC)k is absent) and wherein Q and A are given in table A; WO 2006/058730 PCT/EP2005/012787 65 Table 364: Compounds of the formula la, wherein Y is S, R 1 is H, R 3 is H, R' is CH 3 and k is 0 (i.e. (RC)k is absent) and wherein Q and A are given in table A; 5 Table 365: Compounds of the formula la, wherein Y is O, R 1 is H, R 3 is H, R 5 is H and (RC)k is 4-CI and wherein Q and A are given in table A; 10 Table 366: Compounds of the formula la, wherein Y is S, R' is H, R 3 is H, R 5 is H and (RC)k is 4-CI and wherein Q and A are given in table A; Table 367: 15 Compounds of the formula la, wherein Y is O, R 1 is H, R 3 is H, R 5 is CH 3 and (RC)k is 4 CI and wherein Q and A are given in table A; Table 368: Compounds of the formula la, wherein Y is S, R 1 is H, R 3 is H, R 5 is CH 3 and (Rc)k is 4 20 Cl and wherein Q and A are given in table A; Table 369: Compounds of the formula la, wherein Y is O, R 1 is H, R 3 is H, R 5 is H and (Rc)k is 4 CI, 5-NO 2 and wherein Q and A are given in table A; 25 Table 370: Compounds of the formula la, wherein Y is S, R 1 is H, R 3 is H, R 5 is H and (Rc)k is 4 Cl, 5-NO 2 and wherein Q and A are given in table A; 30 Table 371: Compounds of the formula la, wherein Y is O, R 1 is H, R 3 is H, R 5 is CH 3 and (RC)k is 4 Cl, 5-NO 2 and wherein Q and A are given in table A; Table 372: 35 Compounds of the formula la, wherein Y is S, R 1 is H, R 3 is H, R 5 is CH 3 and (Rc)k is 4 CI, 5-NO 2 and wherein Q and A are given in table A; Table 373: WO 2006/058730 66 PCT/EP2005/012787 Compounds of the formula Ia, wherein Y is OCH 2 (the oxygen atom is attached to the phenyl ring), R 1 is H, R 3 is H, R 5 is H and k is 0 (i.e. (Rc)k is absent) and wherein Q and A are given in table A; 5 Table 374: Compounds of the formula la, wherein Y is OCH 2 (the oxygen atom is attached to the phenyl ring), R 1 is H, R 3 is H, R 5 is CH 3 and k is 0 (i.e. (RC)k is absent) and wherein Q and A are given in table A; 10 Table 375: Compounds of the formula la, wherein Y is OCH 2 (the oxygen atom is attached to the phenyl ring), R 1 is H, R 3 is H, R 5 is H and (RC)k is 4-CI and wherein Q and A are given in table A; 15 Table 376: Compounds of the formula la, wherein Y is OCH 2 (the oxygen atom is attached to the phenyl ring), R 1 is H, R 3 is H, R 5 is CH 3 and (Rc)k is 4-CI and wherein Q and A are given in table A; 20 Table 377: Compounds of the formula la, wherein Y is OCH 2 (the oxygen atom is attached to the phenyl ring), R 1 is H, R 3 is H, R 5 is H and (RC)k is 4-CI, 5-NO 2 and wherein Q and A are given in table A; 25 Table 378: Compounds of the formula la, wherein Y is OCH 2 (the oxygen atom is attached to the phenyl ring), R 1 is H, R 3 is H, R 5 is CH 3 and (RC)k is 4-C1, 5-NO 2 and wherein Q and A are given in table A. The compounds of the formula I may be readily synthesized using techniques generally 30 known by synthetic organic chemists. Scheme 1:
R
4
R
4 RV R3., Ar H Ar AN X ,N \ As ,X ,N \ Q N N AQ N S 1 3 R R R3 Rk R R 31R5 R 3 (11) (I): R 6 = H 35 Compounds of formula I, wherein R 6 is H are obtainable from compounds II by hydrogenation of the C=N-double bond in II according to standard methods of organic WO 2006/058730 PCT/EP2005/012787 67 chemistry well known in the art and described e.g. in US 2002022730, Tetrahedron 1994, 50, 4399-4428, Tetrahedron 2002, 58, 7925-7932 or Trends in Heterocyclic Chemistry 1997, Vol 5, 17-36. 5 Hydrazides I carrying substituents R 6 different from hydrogen are obtainable by functionalyzing hydrazides I with R 6 = H by well known methods such as described in Letters in Peptide Science 2003, 10, 1-9, J. Am. Chem. Soc. 2004, 126, 5366-5367 or Synthetic Communications 2002, 32, 3603-3610 (see scheme 2). 10 Scheme 2:
R
4
R
4 R337P R 6R /" H Ar I Ar A ,XN N A QX 'NN \ 5 1 35 1 3
R
5
R
1
R
3 R R R If individual compounds I are not obtainable by the route described above, they can be prepared by derivatization of other compounds I or by customary modifications of the 15 synthesis routes described. The preparation of the compounds of formula I may lead to them being obtained as isomer mixtures (stereoisomers, enantiomers). If desired, these can be resolved by the methods customary for this purpose, such as crystallization or chromatography, also on optically active adsorbate, to give the pure isomers. 20 Acyl hydrazones of the formula II are known in the art, e.g. from PCT/EP 2004/005681, or they can be obtained applying synthesis methods described for example in WO 87/06133 by analogy. For instance, suitable hydrazides III can be reacted with aldehydes, esters or ketones IV according to scheme 3 to form acyl hydrazones of the 25 formula I1. Scheme 3: 4
,R
4 ,R "2, R2, R Ar ArA
A-Q-X-N(R
5
)-NH
2 + 0 Q N I 1 3 R R R R R (11) (V) (II) 30 The compounds of formula I are effective through contact (via soil, glass, wall, bed net, carpet, plant parts or animal parts), and/or ingestion (bait, or plant part).
WO 2006/058730 PCT/EP2005/012787 68 The compounds of the formula I are in particular suitable for efficiently controlling nematodes and insects. In particular, they are suitable for controlling the following pests: 5 Insects: from the order of the lepidopterans (Lepidoptera), for example Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, 10 Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholitha funebrana, Grapholitha 15 molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, 20 Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scabra, Plutella xylostella, Pseudoplusia includens, Rhyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, 25 Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni and Zeiraphera canadensis, beetles (Coleoptera), for example Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, 30 Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica Iongicornis, Diabrotica 12-punctata, Diabrotica virgifera, Epilachna varivestis, Epitrix 35 hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius califomicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema oryzae, Ortiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllotreta 40 chrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotreta nemorum, WO 2006/058730 PCT/EP2005/012787 69 Phyllotreta striolata, Popillia japonica, Sitona lineatus and Sitophilus granaria, dipterans (Diptera), for example Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya 5 hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pipiens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, 10 Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipula oleracea and Tipula paludosa, 15 thrips (Thysanoptera), e.g. Dichromothrips spp., Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci, hymenopterans (Hymenoptera), e.g. Athalia rosae, Atta cephalotes, Atta sexdens, Atta 20 texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata and Solenopsis invicta, heteropterans (Heteroptera), e.g. Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, 25 Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis and Thyanta perditor, homopterans (Homoptera), e.g. Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis forbesi, Aphis pomi, Aphis gossypii, Aphis grossulariae, 30 Aphis schneideri, Aphis spiraecola, Aphis sambuci, Acyrthosiphon pisum, Aulacorthum solani, Bemisa tabaci, Bemisa argentifolii, Brachycaudus cardui, Brachycaudus helichrysi, Brachycaudus persicae, Brachycaudus prunicola, Brevicoryne brassicae, Capitophorus horni, Cerosipha gossypii, Chaetosiphon fragaefolii, Cryptomyzus ribis, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum 35 pseudosolani, Dysaphis plantaginea, Dysaphis pyri, Empoasca fabae, Hyalopterus pruni, Hyperomyzus lactucae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Melanaphis pyrarius, Metopolophium dirhodum, Myzodes persicae, Myzus ascalonicus, Myzus cerasi, Myzus varians, Nasonovia ribis nigri, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon 40 humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, WO 2006/058730 PCT/EP2005/012787 70 Rhopalosiphum padi, Rhopalosiphum insertum, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Sitobion avenae, Trialeurodes vaporariorum, Toxoptera aurantiiand, and Viteus vitifolii, 5 termites (Isoptera), e.g. Calotermes flavicollis, Leucotermes flavipes, Reticulitermes lucifugus und Termes natalensis, and orthopterans (Orthoptera), e.g. Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, 10 Melanoplus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melano plus spretus, Nomadacris septemfasciata, Periplaneta americana, Schistocerca ameri cana, Schistocerca peregrina, Stauronotus maroccanus and Tachycines asynamorus; Nematodes: 15 plant parasitic nematodes such as root knot nematodes, Meloidogyne hapla, Meloido gyne incognita, Meloidogynejavanica, and other Meloidogyne species; cyst-forming nematodes, Globodera rostochiensis and other Globodera species; Heterodera ave nae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterode 20 ra species; Seed gall nematodes, Anguina species; Stem and foliar nematodes, Aphe lenchoides species; Sting nematodes, Belonolaimus longicaudatus and other Belono laimus species; Pine nematodes, Bursaphelenchus xylophilus and other Bursaphelen chus species; Ring nematodes, Criconema species, Criconemella species, Cricone moides species, Mesocriconema species; Stem and bulb nematodes, Ditylenchus des 25 tructor, Ditylenchus dipsaci and other Ditylenchus species; Awl nematodes, Dolichodo rus species; Spiral nematodes, Heliocotylenchus multicinctus and other Helicotylen chus species; Sheath and sheathoid nematodes, Hemicycliophora species and Hemi criconemoides species; Hirshmanniella species; Lance nematodes, Hoploaimus spe cies; false rootknot nematodes, Nacobbus species; Needle nematodes, Longidorus 30 elongatus and other Longidorus species; Lesion nematodes, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi and other Pra tylenchus species; Burrowing nematodes, Radopholus similis and other Radopholus species; Reniform nematodes, Rotylenchus robustus and other Rotylenchus species; Scutellonema species; Stubby root nematodes, Trichodorus primitivus and other Tri 35 chodorus species, Paratrichodorus species; Stunt nematodes, Tylenchorhynchus claytoni, Tylenchorhynchus dubius and other Tylenchorhynchus species; Citrus nema todes, Tylenchulus species; Dagger nematodes, Xiphinema species; and other plant parasitic nematode species.
WO 2006/058730 PCT/EP2005/012787 71 The compounds of the formula I and their salts are also useful for controlling arachnids (Arachnoidea), such as acarians (Acarina), e.g. of the families Argasidae, Ixodidae and Sarcoptidae, such as Amblyomma americanum, Amblyomma variegatum, Argas persi cus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Dermacentor 5 silvarum, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Omrnithodorus mou bata, Otobius megnini, Dermanyssus gallinae, Psoroptes ovis, Rhipicephalus appendi culatus, Rhipicephalus evertsi, Sarcoptes scabiei, and Eriophyidae spp. such as Aculus schlechtendali, Phyllocoptrata oleivora and Eriophyes sheldoni; Tarsonemidae spp. such as Phytonemus pallidus and Polyphagotarsonemus latus; Tenuipalpidae spp. 10 such as Brevipalpus phoenicis; Tetranychidae spp. such as Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae, Panonychus ulmi, Panonychus citri, and oligonychus pratensis. For use in a method according to the present invention, the compounds I can be 15 converted into the customary formulations, e.g. solutions, emulsions, suspensions, dusts, powders, pastes and granules. The use form depends on the particular purpose; it is intended to ensure in each case a fine and uniform distribution of the compound according to the invention. 20 The formulations are prepared in a known manner, e.g. by extending the active ingredient with solvents and/or carriers, if desired using emulsifiers and dispersants. Solvents/auxiliaries, which are suitable, are essentially: - water, aromatic solvents (for example Solvesso products, xylene), paraffins (for example mineral fractions), alcohols (for example methanol, butanol, pentanol, 25 benzyl alcohol), ketones (for example cyclohexanone, gamma-butyrolactone), pyrrolidones (NMP, NOP), acetates (glycol diacetate), glycols, fatty acid dimethylamides, fatty acids and fatty acid esters. In principle, solvent mixtures may also be used. - carriers such as ground natural minerals (e.g. kaolins, clays, talc, chalk) and 30 ground synthetic minerals (e.g. highly disperse silica, silicates); emulsifiers such as nonionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants such as lignin-sulfite waste liquors and methylcellulose. 35 Suitable surfactants are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, furthermore condensates of sulfonated naphthalene and naphthalene derivatives with WO 2006/058730 PCT/EP2005/012787 72 formaldehyde, condensates of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenyl ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenyl polyglycol ethers, tributylphenyl polyglycol ether, tristearylphenyl polyglycol ether, alkylaryl polyether alcohols, alcohol and fatty 5 alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin-sulfite waste liquors and methylcellulose. Substances which are suitable for the preparation of directly sprayable solutions, 10 emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strongly polar 15 solvents, for example dimethyl sulfoxide, N-methylpyrrolidone and water. Powders, materials for spreading and dusts can be prepared by mixing or concomitantly grinding the active substances with a solid carrier. 20 Granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers. Examples of solid carriers are mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, 25 for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers. In general, the formulations comprise from 0.01 to 95% by weight, preferably from 0.1 30 to 90% by weight, of the active ingredient. The active ingredients are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum). The following are examples of formulations: 1. Products for dilution with water 35 A Soluble concentrates (SL) 10 parts by weight of a compound according to the invention are dissolved in water or in a water-soluble solvent. As an alternative, wetters or other auxiliaries are added. The active ingredient dissolves upon dilution with water.
WO 2006/058730 PCT/EP2005/012787 73 B Dispersible concentrates (DC) 20 parts by weight of a compound according to the invention are dissolved in cyclohexanone with addition of a dispersant, for example polyvinylpyrrolidone. Dilution with water gives a dispersion. 5 C Emulsifiable concentrates (EC) 15 parts by weight of a compound according to the invention are dissolved in xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5% strength). Dilution with water gives an emulsion. 10 D Emulsions (EW, EO) 40 parts by weight of a compound according to the invention are dissolved in xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5% strength). This mixture is introduced into water by means of an emulsifier 15 (Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion. E Suspensions (SC, OD) In an agitated ball mill, 20 parts by weight of a compound according to the invention are 20 milled with addition of dispersant, wetters and water or an organic solvent to give a fine active ingredient suspension. Dilution with water gives a stable suspension of the active ingredient. F Water-dispersible granules and water-soluble granules (WG, SG) 25 50 parts by weight of a compound according to the invention are ground finely with addition 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 ingredient. 30 G Water-dispersible powders and water-soluble powders (WP, SP) 75 parts by weight of a compound according to the invention are ground in a rotor stator mill with addition of dispersant, wetters and silica gel. Dilution with water gives a stable dispersion or solution with the active ingredient. 35 2. Products to be applied undiluted H Dustable powders (DP) 5 parts by weight of a compound according to the invention are ground finely and 40 mixed intimately with 95% of finely divided kaolin. This gives a dustable product.
WO 2006/058730 PCT/EP2005/012787 74 I Granules (GR, FG, GG, MG) 0.5 parts by weight of a compound according to the invention is ground finely and associated with 95.5% carriers. Current methods are extrusion, spray drying or the 5 fluidized bed. This gives granules to be applied undiluted. J ULV solutions (UL) 10 parts by weight of a compound according to the invention are dissolved in an organic solvent, for example xylene. This gives a product to be applied undiluted. 10 The active ingredients can be used as such, in the form of their formulations or the use forms prepared therefrom, eg. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dustable products, materials for spreading, or granules, by means of spraying, atomizing, dusting, 15 spreading or pouring. The use forms depend entirely on the intended purposes; it is intended to ensure in each case the finest possible distribution of the active ingredients according to the invention. Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable 20 powders (sprayable powders, oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetter, tackifier, dispersant or emulsifier. Alternatively, it is possible to prepare concentrates composed of active substance, wetter, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil, and such 25 concentrates are suitable for dilution with water. The active ingredient concentrations in the ready-to-use products can be varied within relatively wide ranges. In general, they are from 0.0001 to 10%, preferably from 0.01 to 1%. 30 The active ingredients may also be used successfully in the ultra-low-volume process (ULV), it being possible to apply formulations comprising over 95% by weight of active ingredient, or even to apply the active ingredient without additives. 35 Compositions of this invention may also contain other active ingredients, for example other pesticides, insecticides, herbicides, fertilizers such as ammonium nitrate, urea, potash, and superphosphate, phytotoxicants and plant growth regulators, safeners and nematicides. These additional ingredients may be used sequentially or in combination with the above-described compositions, if appropriate also added only immediately WO 2006/058730 PCT/EP2005/012787 75 prior to use (tank mix). For example, the plant(s) may be sprayed with a composition of this invention either before or after being treated with other active ingredients. These agents usually are admixed with the agents according to the invention in a weight ratio of 1:100 to 100:1. 5 The following list of pesticides together with which the compounds according to the invention can be used, is intended to illustrate the possible combinations, but not to impose any limitation: 10 Organophosphates: Acephate, Azinphos-methyl, Chlorpyrifos, Chlorfenvinphos, Diazinon, Dichlorvos, Dicrotophos, Dimethoate, Disulfoton, Ethion, Fenitrothion, Fenthion, Isoxathion, Malathion, Methamidophos, Methidathion, Methyl-Parathion, Mevinphos, Monocrotophos, Oxydemeton-methyl, Paraoxon, Parathion, Phenthoate, Phosalone, Phosmet, Phosphamidon, Phorate, Phoxim, Pirimiphos-methyl, Profenofos, 15 Prothiofos, Sulprophos, Tetrachlorvinphos, Terbufos, Triazophos, Trichlorfon; Carbamates: Alanycarb, Bendiocarb, Benfuracarb, Carbaryl, Carbofuran, Carbosulfan, Fenoxycarb, Furathiocarb, Indoxacarb, Methiocarb, Methomyl, Oxamyl, Pirimicarb, Propoxur, Thiodicarb, Triazamate; 20 Pyrethroids: Bifenthrin, Cyfluthrin, Cypermethrin, alpha-Cypermethrin, Deltamethrin, Esfenvalerate, Ethofenprox, Fenpropathrin, Fenvalerate, Cyhalothrin, Lambda Cyhalothrin, Permethrin, Silafluofen, Tau-Fluvalinate, Tefluthrin, Tralomethrin, Zeta Cypermethrin; 25 Arthropod growth regulators: a) chitin synthesis inhibitors: benzoylureas: Chlorfluazuron, Diflubenzuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Teflubenzuron, Triflumuron; Buprofezin, Diofenolan, Hexythiazox, Etoxazole, Clofentazine; b) ecdysone antagonists: Halofenozide, Methoxyfenozide, 30 Tebufenozide; c) juvenoids: Pyriproxyfen, Methoprene, Fenoxycarb; d) lipid biosynthesis inhibitors: Spirodiclofen; Various: Abamectin, Acequinocyl, Acetamiprid, Amitraz, Azadirachtin, Bifenazate, Cartap, Chlorfenapyr, Chlordimeform, Cyromazine, Diafenthiuron, Dinetofuran, 35 Diofenolan, Emamectin, Endosulfan, Ethiprole, Fenazaquin, Fipronil, Formetanate, Formetanate hydrochloride, Hydramethylnon, Imidacloprid, Indoxacarb, Metaflumizon (= 4-{(2Z)-2-({[4-(trifluoro-methoxy)anilino] carbonyl} hydrazono)-2-[3-(trifluoromethyl) phenyl]ethyl} benzo-nitrile), Nitenpyram, Pyridaben, Pymetrozine, Spinosad, Sulfur, Tebufenpyrad, Thiamethoxam, Thiacloprid, Thiocyclam, Spiromesifen, Spirodiclofen, 40 Pyridalyl and the pesticide of the following formula as described in WO 98/05638: WO 2006/058730 PCT/EP2005/012787 76
OCH
3
H
3 C-O O= H 3 C Q\ _0 HN O CH 3 Fungicides are those selected from the group consisting of 5 * acylalanines such as benalaxyl, metalaxyl, ofurace, oxadixyl, * amine derivatives such as aldimorph, dodine, dodemorph, fenpropimorph, fenpropidin, guazatine, iminoctadine, spiroxamin, tridemorph * anilinopyrimidines such as pyrimethanil, mepanipyrim or cyrodinyl, 10 * antibiotics such as cycloheximid, griseofulvin, kasugamycin, natamycin, polyoxin or streptomycin, * azoles such as bitertanol, bromoconazole, cyproconazole, difenoconazole, dinitroconazole, epoxiconazole, fenbuconazole, fluquiconazole, flusilazole, hexaconazole, imazalil, metconazole, myclobutanil, penconazole, propiconazole, 15 prochloraz, prothioconazole, tebuconazole, triadimefon, triadimenol, triflumizol, triticonazole, flutriafol * dicarboximides such as iprodion, myclozolin, procymidon, vinclozolin, * dithiocarbamates such as ferbam, nabam, maneb, mancozeb, metam, metiram, propineb, polycarbamate, thiram, ziram, zineb, 20 * heterocyclic compounds such as anilazine, benomyl, boscalid, carbendazim, carboxin, oxycarboxin, cyazofamid, dazomet, dithianon, famoxadon, fenamidon, fenarimol, fuberidazole, flutolanil, furametpyr, isoprothiolane, mepronil, nuarimol, probenazole, proquinazid, pyrifenox, pyroquilon, quinoxyfen, silthiofam, thiabendazole, thifluzamid, thiophanate-methyl, tiadinil, tricyclazole, triforine, 25 * copper fungicides such as Bordeaux mixture, copper acetate, copper oxychloride, basic copper sulfate, * nitrophenyl derivatives such as binapacryl, dinocap, dinobuton, nitrophthalisopropyl * phenylpyrroles such as fenpiclonil or fludioxonil, * sulfur 30 * other fungicides such as acibenzolar-S-methyl, benthiavalicarb, carpropamid, chlorothalonil, cyflufenamid, cymoxanil, diclomezin, diclocymet, diethofencarb, edifenphos, ethaboxam, fenhexamid, fentin-acetate, fenoxanil, ferimzone, WO 2006/058730 PCT/EP2005/012787 77 fluazinam, fosetyl, fosetyl-aluminum, iprovalicarb, hexachlorobenzene, metrafenon, pencycuron, propamocarb, phthalide, toloclofos-methyl, quintozene, zoxamid * strobilurins such as azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin or trifloxystrobin, 5 * sulfenic acid derivatives such as captafol, captan, dichlofluanid, folpet, tolylfluanid * cinnemamides and analogs such as dimethomorph, flumetover or flumorph. The aforementioned compositions are particularly useful for protecting plants against infestation of said pests or to combat these pests in infested plants. However, the 10 compounds of formula I are also suitable for the treatment of seeds. Compositions for seed treatments include for example flowable concentrates FS, solutions LS, powders for dry treatment DS, water dispersible powders for slurry treatment WS, water soluble powders SS and emulsion ES. Application to the seeds is 15 carried out before sowing, either directly on the seeds or after having pregerminated the latter. Preferred FS formulations of compounds of formula I for seed treatment usually comprise from 0.5 to 80% of the active ingredient, from 0,05 to 5 % of a wetter, from 20 0.5 to 15 % of a dispersing agent, from 0,1 to 5 % of a thickener, from 5 to 20 % of an anti-freeze agent, from 0,1 to 2 % of an anti-foam agent, from 1 to 20 % of a pigment and/or a dye, from 0 to 15 % of a sticker/adhesion agent, from 0 to 75 % of a filler/vehicle, and from 0,01 to 1 % of a preservative. 25 Suitable pigments or dyes for seed treatment formulations are pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1, pigment blue 80, pigment yellow 1, pigment yellow 13, pigment red 112, pigment red 48:2, pigment red 48:1, pigment red 57:1, pigment red 53:1, pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, 30 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. Stickers / adhesion agents are added to improve the adhesion of the active materials on the seeds after treatment. Suitable adhesives are block copolymers EO/PO 35 surfactants but also polyvinylalcohols, polyvinylpyrrolidones, polyacrylates, polymethacrylates, polybutenes, polyisobutylenes, polystyrene, polyethyleneamines, polyethyleneamides, polyethyleneimines (Lupasol®, Polymin®), polyethers and copolymers derived from these polymers.
WO 2006/058730 PCT/EP2005/012787 78 Compositions which are useful for seed treatment are e.g.: A Soluble concentrates (SL, LS) D Emulsions (EW, EO, ES) E Suspensions (SC, OD, FS) 5 F Water-dispersible granules and water-soluble granules (WG, SG) G Water-dispersible powders and water-soluble powders (WP, SP, WS) H Dustable powders (DP, DS) For use against ants, termites, wasps, flies, mosquitos, crickets, or cockroaches, 10 compounds of formula I are preferably used in a bait composition. The bait can be a liquid, a solid or a semisolid preparation (e.g. a gel). Solid baits can be formed into various shapes and forms suitable to the respective application e.g. granules, blocks, sticks, disks. Liquid baits can be filled into various devices to ensure 15 proper application, e.g. open containers, spray devices, droplet sources, or evaporation sources. Gels can be based on aqueous or oily matrices and can be formulated to particular necessities in terms of stickyness, moisture retention or aging characteristics. The bait employed in the composition is a product which is sufficiently attractive to 20 incite insects such as ants, termites, wasps, flies, mosquitos, crickets etc. or cockroaches to eat it. The attractiveness can be manipulated by using feeding stimulants or sex pheromones. Food stimulants are chosen, for example, but not exclusively, from animal and/or plant proteins (meat-, fish- or blood meal, insect parts, egg yolk), from fats and oils of animal and/or plant origin, or mono-, oligo- or 25 polyorganosaccharides, especially from sucrose, lactose, fructose, dextrose, glucose, starch, pectin or even molasses or honey. Fresh or decaying parts of fruits, crops, plants, animals, insects or specific parts thereof can also serve as a feeding stimulant. Sex pheromones are known to be more insect specific. Specific pheromones are described in the literature and are known to those skilled in the art. 30 Formulations of compounds of formula I as aerosols (e.g in spray cans), oil sprays or pump sprays are highly suitable for the non-professional user for controlling pests such as flies, fleas, ticks, mosquitos or cockroaches. Aerosol recipes are preferably composed of the active compound, solvents such as lower alcohols (e.g. methanol, 35 ethanol, propanol, butanol), ketones (e.g. acetone, methyl ethyl ketone), paraffin hydrocarbons (e.g. kerosenes) having boiling ranges of approximately 50 to 250 OC, dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, aromatic hydrocarbons such as toluene, xylene, water, furthermore auxiliaries such as emulsifiers such as sorbitol monooleate, oleyl ethoxylate having 3-7 mol of ethylene oxide, fatty alcohol 40 ethoxylate, perfume oils such as ethereal oils, esters of medium fatty acids with lower WO 2006/058730 PCT/EP2005/012787 79 alcohols, aromatic carbonyl compounds, if appropriate stabilizers such as sodium benzoate, amphoteric surfactants, lower epoxides, triethyl orthoformate and, if required, propellants such as propane, butane, nitrogen, compressed air, dimethyl ether, carbon dioxide, nitrous oxide, or mixtures of these gases. 5 The oil spray formulations differ from the aerosol recipes in that no propellants are used. The compounds of formula I and its respective compositions can also be used in 10 mosquito and fumigating coils, smoke cartridges, vaporizer plates or long-term vaporizers and also in moth papers, moth pads or other heat-independent vaporizer systems. Methods to control infectious diseases transmitted by insects (e.g. malaria, dengue and 15 yellow fever, lymphatic filariasis, and leishmaniasis) with compounds of formula I and its respective compositions also comprise treating surfaces of huts and houses, air spraying and impregnation of curtains, tents, clothing items, bed nets, tsetse-fly trap or the like. Insecticidal compositions for application to fibers, fabric, knitgoods, nonwovens, netting material or foils and tarpaulins preferably comprise a mixture 20 including the insecticide, optionally a repellent and at least one binder. Suitable repellents for example are N,N-diethyl-meta-toluamide (DEET), N,N diethylphenylacetamide (DEPA), 1-(3-cyclohexan-1-yl-carbonyl)-2-methylpiperine, (2 hydroxymethylcyclohexyl) acetic acid lactone, 2-ethyl-1,3-hexandiol, indalone, Methylneodecanamide (MNDA), a pyrethroid not used for insect control such as {(+/-) 25 3-allyl-2-methyl-4-oxocyclopent-2-(+)-enyl-(+)-trans-chrysantemate (Esbiothrin), a repellent derived from or identical with plant extracts like limonene, eugenol, (+) Eucamalol (1), (-)-1-epi-eucamalol or crude plant extracts from plants like Eucalyptus maculata, Vitex rotundifolia, Cymbopogan martinii, Cymbopogan citratus (lemon grass), Cymopogan nartdus (citronella). Suitable binders are selected for example from 30 polymers and copolymers of vinyl esters of aliphatic acids (such as such as vinyl acetate and vinyl versatate), acrylic and methacrylic esters of alcohols, such as butyl acrylate, 2-ethylhexylacrylate, and methyl acrylate, mono- and di-ethylenically unsaturated hydrocarbons, such as styrene, and aliphatic diens, such as butadiene. 35 The impregnation of curtains and bednets is mostly done by dipping the textile material into emulsions or dispersions of the insecticide or spraying them onto the nets. The compounds of formula I and its compositions can be used for protecting non-living material, in particular cellulose-based materials such as wooden materials e.g. trees, 40 board fences, sleepers, etc. and buildings such as houses, outhouses, factories, but WO 2006/058730 PCT/EP2005/012787 80 also construction materials, furniture, leathers, fibers, vinyl articles, electric wires and cables etc. from ants and/or termites, and for controlling ants and termites from doing harm to crops or human being (e.g. when the pests invade into houses and public facilities). The compounds of formula I are applied not only to the surrounding soil 5 surface or into the under-floor soil in order to protect wooden materials but it can also be applied to lumbered articles such as surfaces of the under-floor concrete, alcove posts, beams, plywoods, furniture, etc., wooden articles such as particle boards, half boards, etc. and vinyl articles such as coated electric wires, vinyl sheets, heat insulating material such as styrene foams, etc. In case of application against ants doing 10 harm to crops or human beings, the ant controller of the present invention is applied to the crops or the surrounding soil, or is directly applied to the nest of ants or the like. In the methods according to the invention the pests are controlled by contacting the target parasite/pest, its food supply, habitat, breeding ground or its locus with a 15 pesticidally effective amount of compounds of formula I or with a salt thereof or with a composition, containing a pesticidally effective amount of a compound of formula I or a salt thereof. "Locus" means a habitat, breeding ground, plant, seed, soil, area, material or 20 environment in which a pest or parasite is growing or may grow. In general, "pesticidally effective amount" means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the 25 occurrence and activity of the target organism. The pesticidally effective amount can vary for the various compounds/compositions used in the invention. A pesticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired pesticidal effect and duration, weather, target species, locus, mode of application, and the like. 30 The compounds of the invention can also be applied preventively to places at which occurrence of the pests is expected. The compounds of formula I may be also used to protect growing plants from attack or 35 infestation by pests by contacting the plant with a pesticidally effective amount of compounds of formula I. As such, "contacting" includes both direct contact (applying the compounds/compositions directly on the pest and/or plant - typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds/compositions to the locus of the pest and/or plant). 40 WO 2006/058730 PCT/EP2005/012787 81 In the case of soil treatment or of application to the pests dwelling place or nest, the quantity of active ingredient ranges from 0.0001 to 500 g per 100 m 2 , preferably from 0.001 to 20 g per 100 m 2 . 5 Customary application rates in the protection of materials are, for example, from 0.01 g to 1000 g of active compound per m 2 treated material, desirably from 0.1 g to 50 g per 2 m . Insecticidal compositions for use in the impregnation of materials typically contain from 10 0.001 to 95 weight %, preferably from 0.1 to 45 weight %, and more preferably from 1 to 25 weight % of at least one repellent and / or insecticide. For use in bait compositions, the typical content of active ingredient is from 0.001 weight % to 15 weight %, desirably from 0.001 weight % to 5% weight % of active 15 compound. For use in spray compositions, the content of active ingredient is from 0.001 to 80 weights %, preferably from 0.01 to 50 weight % and most preferably from 0.01 to 15 weight %. 20 For use in treating crop plants, the rate of application of the active ingredients of this invention may be in the range of 0.1 g to 4000 g per hectare, desirably from 25 g to 600 g per hectare, more desirably from 50 g to 500 g per hectare. 25 In the treatment of seed, the application rates of the mixture are generally from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, in particular from 1 g to 200 g per 100 kg of seed. The present invention is now illustrated in further detail by the following examples. 30 The products were characterized by coupled High Performance Liquid Chromatography / mass spectrometry (HPLC/MS), by NMR or by their melting points. HPLC column: RP-18 column (Chromolith Speed ROD from Merck KgaA, Germany). Elution: acetonitrile + 0.1% trifluoroacetic acid (TFA) /water in a ratio of from 5:95 to 35 95:5 in 5 minutes at 40 C. In the examples the following abbreviations are used: m.p.: melting point 40 THF: tetrahydrofuran WO 2006/058730 PCT/EP2005/012787 82 MS: Quadrupol electrospray ionisation, 80 V (positiv modus) RT: retention time Example 1 (compound A-90 of table B): 5 1.1 Furan-2-carboxylic acid N-methyl-hydrazide To a mixture of 3.0 g (65 mmol) of methyl hydrazine in 35 ml of dichloromethane 0.85 g (6.5 mmol) of furan-2-carboxylic acid chloride in 35 ml of dichloromethane were added at 00C within 1 hour. The mixture was allowed to warm to room 10 temperature and stirred for 3 hours. After evaporation of the solvent the resulting oil was sufficiently pure for further reactions (HPLC/MS: RT = 0.707 min, m/z = 140 [M+H]+). 1.2 Furan-2-carboxylic acid N-methyl-N'-[2-methyl-3-(2-fluorophenyl)-allylidene] 15 hydrazide A mixture of 95 mg (0.66 mmol) of furan-2-carboxylic acid N-methyl-hydrazide and 98 mg (0.6 mmol) of 2-methyl-3-(2-fluorophenyl) acrolein in 5 ml of methanol was heated to reflux overnight. After cooling to room temperature and evaporation of the solvent 168 mg (0.59 mmol, 98%) of the desired product were 20 obtained. The compound was sufficiently pure for subsequent reactions (> 90% according to HPLC/MS; RT = 3.640 min, m/z = 287 [M+H]*). 1.3 Furan-2-carboxylic acid N'-[3-(2-fluorophenyl)-2-methyl-allyl]-N-methyl-hydrazide To 114 mg (0.4 mmol) of furan-2-carboxylic acid N-methyl-N'-[2-methyl-3-(2 25 fluorophenyl)-allylidene]-hydrazide and 38 mg (0.64 mmol) of dimethylamine borane complex in 1 ml of dichloromethane which were cooled to 00C 456 mg (2.4 mmol) of p-toluenesulfonic acid monohydrate in 2ml of dichloromethand/methanol 3:1were added. Upon stirring the resulting mixture at 0 0 C for 30 min 2.5 ml of Na 2
CO
3 solution (10% w/v) were added and the mixture 30 was heated to reflux for 30 min. After cooling to room temperature the organic phase was separated and the aqueous phase was extracted twice with dichloromethane. The combined organic phases were dried over MgSO 4 and concentrated in vacuo. 95 mg (0.33 mmol, 83%) of furan-2-carboxylic acid N'-[3 (2-fluorophenyl)-2-methyl-allyl]-N-methyl-hydrazide were obtained which were > 35 90% pure according to HPLC/MS (RT = 3.217 min, m/z = 289 [M+H]). Example 2 (compound A-1 of table B): 2.1 2-Fluorobenzoic acid N'-(3-(3-fluorophenyl)-2-methyl-allylidene) hydrazide 40 WO 2006/058730 PCT/EP2005/012787 83 The title compound was obtained by analogy to the method outlined in example 1.2 by reacting 2-fluorobenzoic acid hydrazide with 2-methyl-3-(3-fluorophenyl) acrolein. 5 2.2 2-Fluorobenzoic acid N'-[3-(3-fluorophenyl)-2-methyl-allyl] hydrazide In a three-necked round-bottom flask (50 ml), fitted with a reflux condenser and a thermometer 1.00 g (3.33 mmol, 1.0 eq) of 2-fluorobenzoic acid N'-(3-(3 fluorophenyl)-2-methyl-allylidene) hydrazide and 314.7 mg (5.34 mmol, 1.6 eq) of 10 dimethylamine-borane complex were equilibrated for 5 min in 10 ml of CH 2
CI
2 at 0 0 C. Then 3.804 g (20.00 mmol, 6.0 eq) of p-toluenesulfonic acid monohydrate were added as a solution in 6 ml of CH 2
CI
2 /MeOH 3:1. After stirring at 0* for 30 minutes 12.5 ml of Na 2
CO
3 solution (10% w/v) and 4 ml MeOH were added and the mixture was refluxed for a further 30 minutes. 15 After cooling to room temperature the organic phase was separated and the aqueous phase was extracted twice with CH 2
CI
2 . The combined organic phases were dried over MgSO 4 and concentrated in vacuo. 0.956 g (3.17 mmol, 95 %) of 2-fluorobenzoic acid N'-(3-(3-fluorophenyl)-2-methyl-allyl) hydrazide were obtained which were > 95% pure according to HPLC/MS ( 1 H-NMR, d 6 -DMSO, 20 500MHz; 8 = 1.9 (s, 3H), 3.5 (d, 2H), 5.5 (pt, 1H), 6.5 (s, 1H), 7.0-7.15 (m, 3H), 7.2-7.3 (m, 2H), 7.3-7.4 (m, 1H), 7.4-7.55 (m, 2H), 9.75 (d, 1H)). The compounds A2 to A321 given in table B, compounds B1 to B56 given in table C, compounds Cl and C2 given in table D, compounds D1 and D2 given in table E, 25 compounds El to E38 given in table F, compound F1 given in table G, compounds G1 to G3 given in table H, compounds H1 to H55 given in table J, compounds J1 to J26 given in table K and compounds K1 to K10 given in table L were obtained by analogy to the methods of examples 1 and 2.
WO 2006/058730 84PCT/EP2005/012787 z z T ++ + + + + + + ,-+ + + + + + + 0 C:) M (D S NN N N N N c E E E EE E E E E~ E~ E E E E m Z m~ m~ N~ C' C,5 '0) ~ 1 1 IC , C;2 C ZQ c1o co o m 001o 0 m--m-------- --------- C: N NVV -C -c a ~ Qa~ ~ .0 c a) 0. Cd ' '. > > -Ca -L 0 0) 2 a C: o EC40 27 2 i x I~ I' 0 JC U)4>%n = a) 60 CD 0 OItU) cu ZM O )T - T r -I- WO 2006/058730 85 PCT/EP2005/012787 . . . . . . .+ + + +- T-. T-++4 .. 11 11 11 11 I I I I I f ii i N NN NN NN ,N 't E co C' LOC~ ~~ CO I- C ) 00 e0 co co N ~ 't C C) 0c 4 3:iC~ 0 ~~ cv~c~')C-~)C) O)
----------------------------
WO 2006/058730 86 PCT/EP2005/012787 M II C) mI mIII I- MI r- C) LO LO MI Il I Nj N (L !N N tlNNN E -- o o o -- --------- -------- C ) C~ , ~ ~ ~ ~ ~ iC C C6 Cfi C- : C~) N c') C6 C') C' C') 04 z C'1 I 5 >15 - U U)C) > U) : C : > C C: N o : a C- 0 00 0 a) = ->-,~_ 0 6L r- o Oo: z ( WO 2006/058730 87PCT/EP2005/012787 + . . . + + + +++ + + + +w z + + +T + +I C.) i 11 11 1 1111H111 i11t11 11 li EE EEEEEEEEE E E E E E E EE EEEE E E Co 0~ 0) (00~ 0)O~ ce 0N M0 CY oo qtO *C m~)*v 00C\JO(Dc tC 0r-F 00 000C 00000 0 07 T7 NN N N 00 C) C a N i\ O0 C 04 iY I~ C6 i I C)00 0000 000 00 N z C-0 1 -~ _N v2 3 > UCL ) C: x c ) _ -- . co C: CL L 0 a) I.0 1 ~~C C' L . C5 0 LO E 0 L c;o E LC 4 a ' E D C\J L6) 6~ co ItL D r- 00) WO 2006/058730 PCT/EP2005/012787 + Cl) 04 ) M0~---~"~- DD M~ MC)G)ON- w 00 0 ) ~ o 040 NNm N N N m Nm CY) l N N N Co N :cE E E E EEE EE EE E E E EE E E EfEEE E ifEE E c EEEEc rO) ) m 0 MN LO (0LO T- ce) w wLO m -qr-; ? c! )C0LON CO (YP cr 7 7 'iN CC C ) N N~ mC mC mCN LL U. U LL -LL U C. I I I I I I I I I I I IT Nt N4C) C c~ ') c ) c ) c ) m ' c ') C ') C'o co co ) C') m' C') 00000000 0 00 C14 N C11 a -I I I I I I I 0 00 E, 0 a 5, a C5 A C C C C: C: c''I ' A' -; > i*LI I = = = = T- a - -, C 1 -5 cL >Lc Lc Lc L0 - 0 -L ~ 0 N C4 4 N -C E E2 E 2 LO C ,-W0 C N M I (D I- w M z << << < < << < < << < WO 2006/058730 PCT/EP2005/012787 . . .+ + + + M + . . . . .+ .. . - .. .~ . .- T r- m m - w w m w' o ( Y Y CLL N~ C) N )L t 4 ) m w m r O T7~ I- m - m 't N "T N ( -- 0> A C > 0) >0) >.)d>C.0 L.0 N N a C: CI 0 ~ ~ a 0-( ~ OC - ~O 0 5 a)c6. 0 a2 c D M0C zr r = 0--=4 WO 2006/058730 90PCT/EP2005/012787 + . . .. . . . . .- . .+ - + + -CU~ ~ ~ -F -C C a uc NNNN N N N N) N) LO NYtI C\JC C ( C)CY 0 if 11 11 11 If 11 f ELN NN N~ ~ NY 0) Q ' N 0 N NY e 0 0 )C oo M0 ~ I 0 0 I~ -y . C ' C - C mC5 m m C o >UC1 U) _ o.o 00U) 0 C) 0~6 0~ -C 0~t~- 6 0 5I E0 a)E a 0.' C- 0-CI N~ C c 5 C s a a) 4-1E 2 0 0 WO 2006/058730 91 PCT/EP2005/012787 + + + . .~ . . . . . .~~ . + + + + + + + + ++ + + + + + + + + +E + + - Y) Cf)) CY) 0N~'C4C~~~4 M M \C NN N NN N N NN N N N ~ EEEEE E E EEE E E E E E LO C\J 0) CD M 0D0U)I' O C) 0 vJ .NtCiC' N N N~ N ~ N NY N6 N C , ~ C-> C ,. > ) CD -C DCL 0 0. '% 0) 0)- (D 0) % CLa , 00 N 2E D~0 w~ 2 0 ,E = 0 0 x 0 0l cL 0 a~- 5C.)0 : a) -y c? Lh4 Or rN a)'r-~~t C COON qt 4-Y "1. z WO 2006/058730 uzPCT/EP2005/012787 + + + + + . +~ + + ++ + + + + SLO co C%4c\~ CCNC~ CI C) e m C' N ~ II 111111 H 111 111 1 II~~ NI ii D~~~~- N!N N N: -~N N E~E EE E E EEE E ~EE EEEE E' O) i- C: C)C")O) (0 (o Ce 0) 1- ._ co c C) ( LO L O I* L C-q 0) C') 0 C) 0' C) M' V-) 0 00 00 0 0000 C- I5; >~ 'c - ci) - C I 0 L9 0) _r CD 5 , 0 C LJ C ?0 N) E L- L-ot 0 0 L (0 0(6(o E LO WO 2006/058730 PCT/EP2005/012787 + + + + + + + + + + + + + + F- F1- F- 3 ++ + + ++ + + + + + + + + + + + if) lii li 1 11 11 11 11 1111 11 11 11 11 N N N N N N N N N N ! M E E EE E E EE E~EE EE EE EEEE E EE CZ) t o D r-- co 0) OO)Oct F- O-- O co- co ( O( LO U) LO r- , -- w coCD -t( ( LO C)LO N U- U.U- U- U-. I LL AO C 4 CO A A 0 L) -II~ I 0 000 00UO00 N CN N Nq N N Nq M MI I 3I( I I 1 G N ~_ cc a C: a aICO CU U a') (1) 0 0 a.~~~ CLC 4COCLC L0 .C LO r coLoJOLO O c 2~0( * ~ ~ ~ ~ ~ a (00006NNNNN E E E< WO 2006/058730 94PCT/EP2005/012787 ca m M- - - I- - F- U) SE EE E E E EE E EEE E0 E~L E E E E E 00~~~~~~~ ~ ~ MN - oM C - tL N M M C) 0) 00 LO m , 0) Cz N 0 O I C C cY) Cim cy C6 C60) 0 N N NL Nq N It C~ C C..4.. 4) ,U)3 U)>~rA U)4 _ 0~-U) U) co co -I-' mc 0 c~c a) (D a).
WO 2006/058730 95PCT/EP2005/012787 + ++ +-Z +Z++ ++ + + -. + T-.+ + T~ T + T.rr m M- M) U) - U) - e) Uf) - -(Y 0. -~ N NNN N N N N 2_ N Nt~ E'E (0 -r o CD N CO LO CO n0N O)4 C> ) 000 co L M CCC C C C C C C C 04 C 4 C y) C, C C Uo NO U) U ) N) m) U) C)) U) m ) U ) U U) ) U ) U cl'4 C C
-----------------------------------
c.'4 ~ ~ ~ ~ L to m0NOOO C'tOO-( 6O m m0 0 3: = 3z:mcq No C WO 2006/058730 96 PCT/EP2005/012787 + . + + + + + + + + + + + + + + + + + + + + +a +) TzI I cy)0) ( Lo LO 0) m mL m ML M c) CY C) -- V- C) C) NN NNN N N N NNNNNNNN E EE EEE E EE E EE EE EE E SE E E EE EE E E EEE E ce) CD "t m 0 m C - O C T r t , * - oo m LO m " m' NC C~) I? - ~L0 004 0j~ N z - c\J CU C6) 00C) jc 0 c"J AI C" 000 c a)C CD CL a :Ma) c q 0) 2~ o' 5 o )0 0 0 0 0 (N (4 (' (N '4 ( C: cc c c C c L (D a) a) a) C) a) a) a0 a o o 0- CL a0 Ccc cc C :c:c: 0 0 0 00 0 0 00 CCLD.0 qI Z-- =I qI q Ir- I c C'4 C'C4C0C4 N N (4 NCN a) U' ~ L)C (0r- CC)O 6 C1 N'C4" N\ C'J'l~ N O m z !
!
WO 2006/058730 PCT/EP2005/012787 m m ++ + T+ +++++ + + +++ C0 co 0 N () )0M C 0 c NI C. N~! N 2 N! N N - N EE E ~E E EE E E E ffE E ~ E *EE ' E E -EE 001- U) . 0 C' C~ q , t c D T - 1,0 oo 1 00 CY) 0) C CD 0 r- (0 00 - (0 ( U-) U C') 6 j o C M C 6 o Ci c N NN NO M CC a ~ ) 5, o 0 a)c mc3 CL~ .0 a) q C) cc 2 c cC) 2 2 Cc CL 0 L0 0 L0 N c~~ c C: c C: c c N c a ~c) 6 a) a)z a) UL ) a) a ) a) 4a) U) z ? a 511= = _:= r c- r WO 2006/058730 9aPCT/EP2005/012787 + + + + + + + + + + + + + +++ ++ + +++ E E E E E E E :2 2 E E 2 E E E : N N~~ N N N N N l N N- N 0 ~ cC , 04 r-) 04 ) It 't 0) C: ~ l0 c> o) -~ 0.) U 0c 0 c c cc coc cc m U) U) U) U) LL LL UU U UU) U) UU L) iU) U) U ) ) 0000000000iC6C6C coo 000 00 000 N ~~'CN co tOL ~~'CO(0 0 0 0 0 (000 0 WO 2006/058730 99PCT/EP2005/012787 .~ ~++ . . . .++~ . . .+ -u - - -- - .- ------- X C/) I- m I- Cm N-C m - 't N' Lo (N (0 C) M (o 0 qti r-- r-- T- T- wt ( t(. ~) 0 - ~ 0 -~NNNN N NN N N N N N NN ~ ~ E EE E E E E E E E 'EE E C') ,t ,t ) (o r, I. m C co V- V-- a co N J. c U) (0 - C') N-C CC w - C) M C D) 'I C~~~qN C')c ( c
----------------------------------------------
6 e~~~~~,~U cU-~C, C) C' ' ' ' M ~ ~ ~Nf 3: : :' c c c M 30 0 1 1 1 C')) N C4 J C 0 M3:N 100 M~ 0 N) (-) - ) U -) U ) U 0u . 0. 0. a a 0a 4- 0" 0o U)) ~ 2 22 2 .C- C 0 0 0 0 0 C 0 CL CL CL U) =i : o N 04J CN N (NI (N ------------------------
-----------------------
z-(00~(C).U(NC~~(JC)' WO 2006/058730 100 PCT/EP2005/012787 . . . . . . .+ + + _ u m~ cu -C w~~ CU (Y) -D - -~ - ( ) 00 co c, c U) i N (0N m m C) E c B.-.-,1.-1 N~ + EEE E E E E 7 O0 ) f'- U- CD Cf) I- C) (0 co 0)0) C. 00 C) N 00 't co~ , r,- -) M m w T C o CD T- CO 0) 04COic5N C NN C Cco C'5CoiC,5 C , 6 ----------------------- 0 0 0 0 -0r' Mo co N o CYo OR 20 2 0 00 0 0 0 0 00 7 7 C4 C4 C~ q C Cq cl C4 ci C4 0' 0 0 a) C1 ) C) a C) C) a) (1 6 i I ) 0 ) 0 .C Y c o .c e .c~ ~c e C) .C Y - C Z .C z <22 22 2 2 WO 2006/058730 101 PCT/EP2005/012787 + + + + + + + + + M + ~ '. L . p.. LO MO O CO wO m~ MoC LO CM C ) - -j CL EE E E EEEE E E E E E E 02 ,,- 0 c' 0r 0) 1- r- (D CO oC I,- CN CD 0) ( O V - 0D NW mo mo m C6 C6 mo C6 C6 C6 Co 0 0 Co -0 C'4 C L( &l CCIO 0 ) 0- 0 a) ) a) a) a) a) a ) 0a) ) =C = .C aC .c .C -C c~ = = 0 0 0 0 0 0 0 0 0 0 V -0 -0 Vy - 0 y 0 Y VY N4N CiNN NNF Nl ~ ~fCf I az C~l ce5 C) C~l H 1 Uz WO 2006/058730 PCT/EP2005/012787 + + + + + + + + + ++ CO+ C-) II I I I I I I I I I I It I I NioW0MMM4 -U) )m0MmNML CL m e ~)C)CjC)m (Y 4 C)()c f 2 11 1 f 11 1 1 1 I E-N N---N N N E EE EE EE EE G- EOOEOOEOOOOOOOOS c) E E E E E E E E E E E E E E E E E 0) C CO T- M -- - ( CO C) , M CO t 0 rl C~ T-co, o' I-2:( , D r-c t t N c - - m M m N " o 1 00 .C > . .c . .c . .c . . .) .~ . .) .c ( _ C -51 ~~>x C: C :C : : c : 0 I D a)I ) (D s a. -C C 6L0 .i o .2 WO 2006/058730 103 PCT/EP2005/012787 + + + + + .+ +, + + + + + :T- - - - -- - - m~ w~ mZ ca cu ~~~~+ + + + + + + . + .+ (D co LO MI (0 V- C-- MI MI oo MI I I I- NI N NN NN N N N NN N E E E E E E E E E E E E E E E E)O 00 0 0 0 00 C OL ) 0 x cC c >C5 .( ') - a)C -a2-~ ) a) _a - (.C 0 )D~ CL E cLDo = 2~ 2 CL Ci) 0> < ~ ~ ~ ~ U '0xoo0')o o a. E4 E Cl - L-R: CL- m c 0 0 0 L * * .- r a C) : o a ~ 0==c Q) 0 > 'I U4 WO 2006/058730 PCT/EP2005/012787 -- F-,+-+ + CL Nmmmmmmmm N N 1 E E EEEEE 0- OOOOOOOQ.- .- zs EOO U I 0 o LO M 't V LO. 0) I~ I Y Go 0 0000 0 000 w0 0 0 00 n5 -73 3: M - X C M 3 X 3 _ 0 0 00 0 0 c *R] mi 3: 3: 3: 0 0 m m 0 m C >, o -o 0. 0 W U)q >~> 0 0==0 co CD 0 5U) U)0 L9 c U C ~~I I- - > 1ub, WO 2006/058730 PCT/EP2005/012787 T, - 00 NY N C)~ Et E C\! o:q + + - Cu c II ) ONN / 'E U-/ E ' A( Iz IocoaZ Z-Qll oo a~a) 0 CL
L
00 0 4-1 -2N '4 W LL 6,6~ Zuz Q-C ZOO H O IUD WO 2006/058730 PCT/EP2005/012787 + -+ + + + + + + + + + o + a a + m +- + 2+ C") M~ -n 2: *I - a: O O O Z 0) m' I-- m) +2: L l N C N 0) N N N t- N N N! NOC ' E E E 'E cE E E E 2 E 2 EY (- C\O 0 0 4 20) 0) T- - C\J '-) co) LOC) I It 0) \ 0 C)c Qco00 C: 04 q Ill:- Y) 0 0 CNLO C C C' ci C C4 C' C\IC -: CC a) D C'4 2 ~ ~N C!' =3 Ito c, mo v C; Nv N N N o 0 0 0 ) _~~c co 0 -o m ~ . C . - ~ 0 00 0.~~~~~ 0. 0. 0 . 0 0 ~ C'! C'! C'! C C'! 0 4I 4r = Ir =, N" N' C'! N' C"4 o - C\! m" .I- Lo (0 r- w m)0 m~ ' "It L O CO z w w u Uiul w ww w w L 1Uf WO 2006/058730 PCT/EP2005/012787 E z zz-rzzz zzzz zza E+ ++ +++ ++++ z , .,, .. ,, ,, .,, ,, ,, . .,7 ... + M cem +c c) N m m 0e0 C o + o (Y) 0) (N) + II II II II II II II II I II II .. - -. N - - - - '-- - - . N E E E EEE E E E E EE >,o> c o m , >,p o o o o . a - e -m o ° o o o o i E E E E E E E E 2E E E c: N EE o .o-o CoIO IIII - 0 0 CO 0 N CO 0 CO - - - v -;- m o It m m .1. . . JJ J 0. 10. W ,I0.0 UJ I 0. 1I 0 0 W UJ I N( N 0 (N I (N 0 o 0I- -r -5 3E 0 If) 1001 "51 001 -; 5w 3I 0 00 0 00 <~ 5,, 2, 2 2~ SO- C" 2 C C C a~>> ,> 0 0 0 0 0 0 0 I 00C =0 0 0 02 02 r, Ir qF I -. I. (N (N ( (N (N (N (N 6 r- M M0) 0 - (N MO "t LI M N m 0M 0 V- (N MO 't Z - - (N N (N N (N (N (N (N MO M O M O M LU LU LU oU LU LU L L W L Lo LU oLo WO 2006/058730 108 PCT/EP2005/012787 E+ + + + "0 0o (0 00 CD CUN N C NJ C) E I II EM + ~EEEE E C)LO rrH E LOO N) co =< / I IY z-nC CL 0L 0 0 -:3 47 C1 NN Z~ c c C') co) Ccu Ill w w wH
LO
luv, WO 2006/058730 PCT/EP2005/012787 CU Z II _ C/ N 0) L CLo 0C1)) C') co 6- \ - _ zOOS -0/\ Z 00 WO 2006/058730 110 PCT/EP2005/012787 + + + + + + + + + + .
+ + + + + + + + + + +.... c') (oo m'~ ,I* I-i C) mo O )~0 IEE E EEE E E EE E EE EE E C"j (o V-0) U') T- CN 0) N' MO L O CO (4~ r-- V) CNI 00 CO 1- 04 T- 0)0C C C? U- t CO T- M It "I CO N,- U- V l to N- O r* LL LLLL LL LL CO)CO) m 0O C C40- -c 05 N 2 E o ~~ 2 E 0 L) *0 CLJ V 0 3: C ) 0 0 c C 0 C o- a ~) bU M a . ) Oto = E 0-r-C E 0.4 N C) C C C) C) C) C C C ) C) C C C C C C a) a) a) a) a) a) a) a) a) a) a) a) a) a) a) a) a) =C c -a C -C - C -C =C C -C -C = -C = C <2 2 22-2202222 2 L-22 22 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 n n =3 = n = 04 N~ N~ 0N N\ N N~ N 04 N 04 N Nq N N~ N CN 6 -N CO V -to CO ND- O00 TN COT V- VIO - WO 2006/058730 11PCT/EP2005/012787 S N r-J N (N a CO) 00 T- C'4 C) T N N N N~ N~- N 4- N N C- I E E EE E EE E EE E E o q. CD 00) (0 ) (N (N 0 It0 CO CO ce "l 03 (0 Co - 0) It co (D m 0) 0 1- 03 ce t co LI L I IL L LL UL UL IL CO CO) CO) CO CO CO CO COA 0 o (N ->1 02 0 o ~ 0 ON 0 cuM N 11 0) 7- U) 0 M 0 ) = a0 C C: C =3 ~ CL m CO C\! a) EY c ____ (DJ 00000 00 0 00 0 -5 I 5£ 1 15 I5. I5 I 1 I 5 I ' 1 5 I I5 I5 c a c c c a CC cC C: c c c C: C ) a) a) w) a) a) a) a) a) w) a) a) '' (D (D a) = C _ . _ C = - C = = -~C -a .c =C C =~ rZ 0 0S 0 0 00 0 - 0 0 0 00 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 00 0 0 0 n ~ ~ ~ ~ ~ ~ ~~: m 3: I I I II I I IF I ; I I (NJ (NJ (N (NJ (NJ (NJ ( C '! (N C4 0 C' (N 04 C'! (N (N 00 00)0 C) 04 CO) I~t Lo) (D O 00 0 C)- (N CO) 0 - V~- (N ' (N (N C'! (N 04J (J (N 04J CO CO CO WO 2006/058730 PCT/EP2005/012787 + + + M + +M + +M + + + CN N 4N N CD' CO T-J N T- 0' O0( Nr D Ny C6 m~ 'C6 cy 0) U - U.. LL U- LL LL U. U.. U.. L U.. 0 0 0 1C----5 0 M 0 C') o E ~ 0 0L (0) U) E -m 0- E xU q 0z 0c 2:0U) -C U) 1 :3CC)QIq La a)~ 0C N E rp-c C. C- C a ) CL CL 'r CL C\- E T- CC F C) U) U) m) Um ) U) U) m) U) ) m) U) m) Cl) U) Uo a)) QO ~ ) W a) (N a) C' ) t () a) a)D a)0a C) CL) a' a' a- a. a~ a ai 0- CL 'CL 0- t a~ CL WO 2006/058730 113 PCT/EP2005/012787 z + + + + +~ . + + + 0. N N N+ + + + I-. ) M I- U + +Y 0 +" E E *E E L() U- U- - U O OO t C6 ~ WC O A'. CoCo 0.. N N4 N ALL LE- U.o mi Lm Co C C: Co Mo a: M m) N-D ca C', !E W 0 99900 U) C14 M mIz ~LL Li- Li Li Li- LL- LL LL a: M M m M 3;3a -~~~~~c -5-;> -;c.)C a) 0 0. 0 0. 0L NE 2 <2 222 2 "0-~ ti 4- I -P qI I~ CN N N N~ N~ \ 6 C~- N Co C * to i LO to W O Z Z 1 1 "I" LI) WO 2006/058730 114 PCT/EP2005/012787
-----------------------------------
- -u -u - - - - -u -u - C)O C ( w L (N C o-(J ~ CD (N Cm wo 0 C0 E wO ( CD w . (N 't wo Cm w 0 N(L N N. N N N N Tl -T Lo) CD (0 CO) 0) qT N- 00 00 r- CD0( CO) m m CO CD C~- Co COci - Ci y U-' U L L U- LL U- LL U- U- LL LL LL U- LL LL LL L CO CO 0- - D 0 C.) C: co 2 . 0 0 CO 0OC . C OC o C) CL) c coc a) CL U) -5 CL a) a - 0 L 0 CL ~ 0. CL 00 " ~ ( (N( o N =N (N (N qN 0C4 1 = =OC -C 0 ( CO :3IC CD N- CE 0)0 -( Z ; -y =1 47 'Y 7
-----------------------------------------------
WO 2006/058730 15PCT/EP2005/012787 +- + + T + + +. C) E E E E U) CD - (o zEE~ E SE E E E V- CN NC U>- /L LL IZ-O 0 II 0/ c CO) -CC CL a CL Q LO 2 ILCLaC IC) I)t ) ( Cl N Cl C4 NC NC 0C N )U) 04 N' C\J cu 6 z ' iC"J C\
-JO
WO 2006/058730 lbPCT/EP2005/012787 z z + + + 00 T-- r- C% CO ) C~ ~ N N EE E E E E r- 0 LO0 C) c0 C) CL 0 ~0 0 47: :3 N = = I1 I0 (NI ('4 WO 2006/058730 117 PCT/EP2005/012787 The action of the compounds of the formula I against pests was demonstrated by the following experiments: 5 I Activity against insects 1.1 Cotton aphid (aphis gossypi) The active compounds were formulated in 50:50 acetone:water and 100 ppm 10 Kinetic® surfactant. Cotton plants at the cotyledon stage (one plant per pot) were infested by placing a heavily infested leaf from the main colony on top of each cotyledon. The aphids were allowed to transfer to the host plant overnight, and the leaf used to transfer 15 the aphids was removed. The cotyledons were dipped in the test solution and allowed to dry. After 5 days, mortality counts were made. In this test, compounds A1 0, Al 1, A16, A1 9, A21, A44, A47, A63, A68, B11, B20 and B25 at 300 ppm showed over 75% mortality in comparison with untreated 20 controls. 1.2 Green Peach Aphid (Myzus persicae) The active compounds were formulated in 50:50 acetone:water and 100 ppm 25 Kinetic® surfactant. Pepper plants in the 2 nd leaf-pair stage (variety 'California Wonder') were infested with approximately 40 laboratory-reared aphids by placing infested leaf sections on top of the test plants. The leaf sections were removed after 24 hr. The leaves 30 of the intact plants were dipped into gradient solutions of the test compound and allowed to dry. Test plants were maintained under fluorescent light (24 hour photoperiod) at about 250C and 20-40% relative humidity. Aphid mortality on the treated plants, relative to mortality on check plants, was determined after 5 days. 35 In this test, compounds compounds A13, A51, A70, A74, A75, A79, A80, A81, A83, B1, B22 and B34 at 300 ppm showed over 75% mortality in comparison with untreated controls.
WO 2006/058730 118 PCT/EP2005/012787 1.3 Orchid thrips (dichromothrips corbetti) Dichromothrips corbetti adults used for bioassay were obtained from a colony maintained continuously under laboratory conditions. For testing purposes, the 5 test compound was diluted to a concentration of 500 ppm (wt compound: vol diluent) in a 1:1 mixture of acetone:water, plus 0.01% Kinetic® surfactant. Thrips potency of each compound was evaluated by using a floral-immersion technique. Plastic petri dishes were used as test arenas. All petals of individual, 10 intact orchid flowers were dipped into treatment solution for approximately 3 seconds and allowed to dry for 2 hours. Treated flowers were placed into individual petri dishes along with 10 - 15 adult thrips. The petri dishes were then covered with lids. All test arenas were held under continuous light and a temperature of about 280C for duration of the assay. After 4 days, the numbers of 15 live thrips were counted on each flower, and along inner walls of each petri dish. The level of thrips mortality was extrapolated from pre-treatment thrips numbers. In this test, compounds A1, A2, A12, A141, A149, A 155, A173, A218, A223, A260, A301, A303, A305, A319, C1, E3 and E42 at 300 ppm showed over 75% 20 mortality in comparison with untreated controls. 1.4 Bean Aphid (Aphis fabae) Nasturtium plants grown in Metro mix in the 1 st leaf-pair stage (variety 'Mixed Jewel') were infested with approximately 2-30 laboratory-reared aphids by 25 placing infested cut plants on top of the test plants. The cut plants were removed after 24 hr. Each plant was dipped into the test solution to provide complete coverage of the foliage, stem, protruding seed surface and surrounding cube surface and allowed to dry in the fume hood. The treated plants were kept at about 25°C with continuous fluorescent light. Aphid mortality is determined after 3 30 days. In this test, compounds A93, A141, A305, El, E3 and K6 at 300 ppm showed 75% mortality in comparison with untreated controls. 35

Claims (24)

1. An hydrazide compound of the general formula I R 4 6 2. RI R I Ar (I) Q N 15 1 3 5 R R R and the salts thereof, wherein ..... is absent or a covalent bond; 10 A is a cyclic radical selected from phenyl and a 5- or 6-membered heterocyclic radical with 1 to 4 heteroatoms as ring members which are selected, independently of one another, from O, N and S, the 5- or 6 membered heterocyclic radical may have a carbonyl group as ring member 15 and where the cyclic radical may have 1, 2, 3, 4 or 5 substituents R a which are selected, independently of one another, from halogen, cyano, nitro, Cj Clo 0 -alkyl, C 1 -Clo-haloalkyl, C 3 -C 1 o-cycloalkyl, C 3 -Co 10 -halocycloalkyl, C 2 -Co 10 alkenyl, C 2 -Co 10 -haloalkenyl, C 2 -Co 10 -alkynyl, C 3 -Co 10 -haloalkynyl, C 1 -C 10 alkoxy, Cl-Co 10 -haloalkoxy, C 2 -Co 10 -alkenyloxy, C 2 -Co 10 -haloalkenyloxy, C2 20 C 10 o-alkynyloxy, C3-Co 10 -haloalkynyloxy, C 1 -Co 10 -alkylthio, C 1 -Co 10 -haloalkylthio, C 1 -Co 10 -alkylsulfinyl, C 1 -Co 10 -haloalkylsulfinyl, C 1 -Co 10 -alkylsulfonyl, C 1 -Co 10 haloalkylsulfonyl, hydroxy, NR 7 R 8 , C 1 -C 1 0 -alkoxycarbonyl, C 1 -Co 10 haloalkoxycarbonyl, C 2 -Co 10 -alkenyloxycarbonyl, C2-Clo haloalkenyloxycarbonyl, C 1 -Clo-alkylcarbonyl, C-Clo-haloalkylcarbonyl, 25 R 7 R 8 N-CO-, phenyl, benzyl and phenoxy, wherein phenyl, benzyl and phenoxy may be substituted by 1, 2, 3, 4 or 5 substituents Rb which are selected, independently of one another, from halogen, cyano, nitro, Cj-Co alkyl, Cl-Co 10 -haloalkyl, C 3 -Clo-cycloalkyl, C 3 -Co 10 -halocycloalkyl, C2-C10 alkenyl, C 2 -Co 10 -haloalkenyl, C 2 -Co 10 -alkynyl, C 3 -Co 10 -haloalkynyl, C1-Co10 30 alkoxy, Cl-Co 10 -haloalkoxy, C 2 -Co 0 -alkenyloxy, C 2 -Co 10 -haloalkenyloxy, C2 C, 0 -alkynyloxy, C3-Co 10 -haloalkynyloxy, Cl-Co 10 -alkylthio, Cl-C 1 o-haloalkylthio, Cl-Co 10 -alkylsulfinyl, Cl-C 0 lo-haloalkylsulfinyl, Cl-C0o-alkylsulfonyl, C-Cjo haloalkylsulfonyl, hydroxy, NR 7 R 8 , C-Co 10 -alkoxycarbonyl, Cj-Clo haloalkoxycarbonyl, C 2 -Co 10 -alkenyloxycarbonyl, C 2 -C 1 o 35 haloalkenyloxycarbonyl, C-Co 10 -alkylcarbonyl, Cl-Clo-haloalkylcarbonyl and R 7 RBN-CO-, wherein in each case two radicals R a which are bound to WO 2006/058730 PCT/EP2005/012787 120 adjacent carbon atoms may form a CH=CH-CH=CH moiety or a O-CH 2 -O moiety, where in these two moieties 1 or 2 hydrogen atoms may be replaced by a radical Rb as defined above; 5 Q is selected from the group consisting of a single bond, C1-C4 alkylidene, O-C1-C4 alkylidene, S-CI-C4 alkylidene and NR 9 -C 1 -C 4 alkylidene, wherein the alkylidene group in the last four mentioned radicals is unsubstituted or carries 1, 2, 3 or 4 substituents selected from OH, =0, halogen, C1-C4 haloalkyl and C1-C4 alkoxy; or 10 A-Q may together be C 1 -Co 0 -alkyl, which may be substituted by 1 or 2 substituents selected from the group consisting of =0, OH, C 1 -C 4 -alkoxy, Cl-C 4 -alkylthio, halogen or C,-C 4 -alkylcarbonyloxy; 15 X is C=O, C=S or SO 2 ; Ar is an aromatic radical selected from phenyl, naphthyl, pyridyl, pyrimidyl, furyl and thienyl, where the aromatic radical may carry 1, 2, 3, 4 or 5 substituents Rc which are selected, independently of one another, from 20 halogen, cyano, nitro, C0 1 -Co 0 -alkyl, C 1 -C 10 -haloalkyl, C3-CIo-cycloalkyl, C3 C10o-halocycloalkyl, C2-C 1 0 -alkenyl, C2-C 10 -haloalkenyl, C2-C 10 -alkynyl, C3 Co 10 -haloalkynyl, C 1 -Cl0o-alkoxy, Cl-Clo-haloalkoxy, C 2 -Clo 0 -alkenyloxy, C2 Co 10 -alkynyloxy, C3-C 10 -haloalkynyloxy, C-C 10 -alkylthio, C0 1 -C 10 -haloalkylthio, Cl-Co 10 -alkylsulfinyl, C0 1 -Co 10 -haloalkylsulfinyl, Cl-C 10 -alkylsulfonyl, Cl-Co0 25 haloalkylsulfonyl, hydroxy, NR 7 R 8 , C 1 -Clo-alkoxycarbonyl, C-Co haloalkoxycarbonyl, C2-C1 0 -alkenyloxycarbonyl, C2-C1 0 -haloalkenyloxy carbonyl, C 1 -Co 10 -alkylcarbonyl, Cl-Co-haloalkylcarbonyl, C-Co0 alkylcarbonyloxy, R 7 R 8 N-CO-, phenyl, benzyl and phenoxy, wherein phenyl, benzyl and phenoxy may be unsubstituted or substituted by 1, 2, 3, 4 or 5 30 substituents Rb as defined above, and wherein two radicals Rc which are bound to adjacent carbon atoms may form a O-CH 2 -O moiety, where in said moiety 1 or 2 hydrogen atoms may be replaced by a radical Rb as defined above; 35 R' is selected from the group consisiting of H, C-C0lo-alkyl, C 1 -Clo-haloalkyl, C3-Cl 0 -cycloalkyl, C3-C 10 -halocycloalkyl, C2-Co 10 -alkenyl, C2-Co 10 -haloalkenyl, C 2 -C 10 -alkynyl, C 2 -C 10 -haloalkynyl, phenyl and a 5- or 6-membered heterocyclic radical with 1 to 4 heteroatoms which are selected, independently of one another, from O, N and S, it being possible for the WO 2006/058730 PCT/EP2005/012787 121 aforementioned two last radicals to be unsubstituted or substituted by 1, 2, 3, 4 or 5 substituents R a as defined above; R 2 is a monovalent radical selected from H, halogen, cyano, C 1 -Cl 0 -alkyl, C 1 5 Clo-haloalkyl, C 3 -C lo-cycloalkyl, C 3 -C 1 o-halocycloalkyl, C 2 -Clo-alkenyl, C2 C 10 o-haloalkenyl, C 2 -Clo-alkynyl, C 3 -Co 10 -haloalkynyl, C-Co-alkoxy, Co-Co haloalkoxy, C 2 -C 10 -alkenyloxy, C 2 -Co 10 -haloalkenyloxy, C 2 -Co 10 -alkynyloxy, C 3 -Co 10 -haloalkynyloxy, C 1 -C1o-alkylthio, C 1 -C 1 0 -haloalkylthio, hydroxy-C 1 Clo-alkyl, Cl-Co 10 -alkoxy-C 1 -Co 0 -alkyl, halo-Cl-Clo-alkoxy-C-Clo-alkyl, Cl 10 Co 10 -alkoxycarbonyl-C l -Co 0 -alkyl, halo-C 1 -Co 10 -alkoxycarbonyl-C l -Clo-alkyl and phenyl which may be substituted by 1, 2, 3, 4 or 5 substituents Rb as defined above; R 3 is selected from the group consisiting of H, halogen, cyano, C 1 -C 1 o-alkyl, 15 Cl-C 1 0 -haloalkyl, C 3 -C 1 o-cycloalkyl, C 3 -Co 10 -halocycloalkyl, C2-C0o-alkenyl, C 2 -Co 10 -haloalkenyl, C 2 -Co 10 -alkynyl, C 3 -C 10 -haloalkynyl, Cl-Co 10 -alkoxy, C Clo-haloalkoxy, C 2 -C 0 -alkenyloxy, C 2 -Co 10 -haloalkenyloxy, C 2 -C 10 alkynyloxy, C 3 -Co 10 -haloalkynyloxy, Cl-Co-alkylthio, Cl-Co 10 -haloalkylthio, hydroxy-C-Co 0 -alkyl, Cl-Co 10 -alkoxy- C 1 -Co 10 -alkyl, halo-Cl-Co 0 -alkoxy-C 1 20 Clo-alkyl, C,-Co 10 -alkoxycarbonyl-C l -Clo-alkyl, halo-Cl-C 1 o-alkoxycarbonyl C 1 -Clo-alkyl and phenyl which may be substituted by 1, 2, 3, 4 or 5 substituents Rb as defined above; R 4 is hydrogen or has one of the meanings given for Rc or 25 R 4 together with R 2 is a bivalent radical, which is selected from O, S, CR 1 o=N, N=N, O-CR"R 1 2 , S-CR"R 1 , N(R 13 )-CR"R 12 , O-C(0), O-C(S), S-C(0); N(R 1 3 )-C(0) or N(R 13 )-C(S); 30 R 5 is selected from the group consisiting of H, C-Clo-alkyl, Cl-Co 10 -haloalkyl, C 3 -Clo-cycloalkyl, C 3 -C 1 o-halocycloalkyl, C 2 -Co-alkenyl, C 2 -C 1 0 -haloalkenyl, C 2 -Co 10 -alkynyl, C 2 -Co 10 -haloalkynyl, benzyl and phenyl wherein benzyl and phenyl may be substituted by 1, 2, 3, 4 or 5 substituents Rd which are selected, independently of one another, from halogen, cyano, nitro, C-C 10 35 alkyl, C 1 -Co 10 -haloalkyl, C 3 -Co 10 -cycloalkyl, C 3 -Co 10 -halocycloalkyl, C2-Co10 alkenyl, C 2 -C 1 0 -haloalkenyl, C 2 -C l 0 -alkynyl, C 3 -Co 10 -haloalkynyl, C1-Clo alkoxy, Cl-Co 10 -haloalkoxy, C 2 -Co 10 -alkenyloxy, C 2 -Co 10 -haloalkenyloxy, C2 Clo-alkynyloxy, C 3 -Co 10 -haloalkynyloxy, C 1 -Co 10 -alkylthio, C-Co 10 -haloalkylthio, C-Clo-alkylsulfinyl, C 1 -C 1 o-haloalkylsulfinyl, Cl-Co 10 -alkylsulfonyl, C-Clo 40 haloalkylsulfonyl, hydroxy, NR 7 R 8 , C-Co 10 -alkoxycarbonyl, C-Co- WO 2006/058730 PCT/EP2005/012787 122 haloalkoxycarbonyl, C 2 -Co 10 -alkenyloxycarbonyl, C 2 -Cl o haloalkenyloxycarbonyl, C 1 -Co 10 -alkylcarbonyl, Cl-Co 10 -haloalkylcarbonyl and R 7 R 8 N-CO-; 5 R 6 is selected from the group consisiting of H, C 1 -Co 10 -alkyl, which is optionally substituted by CN or NO 2 , C 1 -Co 10 -haloalkyl, C 3 -Co 10 -cycloalkyl, C 3 -Co 10 halocycloalkyl, C 2 -Co 10 -alkenyl, C 2 -Co 10 -haloalkenyl, C 2 -Co 10 -alkynyl, C 2 -Co 10 haloalkynyl, Cl-Clo-alkylthio, C 1 -C 10 O-haloalkylthio, C 1 -Co 10 -alkylsulfinyl, Cj Cl-haloalkylsulfinyl, C 1 -Co 10 -alkylsulfonyl, C 1 -Co 10 -haloalkylsulfonyl, Cj-Cso 10 alkoxycarbonyl, where the alkyl moiety of alkylcarbonyl may be unsubstituted or substituted by 1, 2 or 3 substituents selected from the group consisting of C 1 -Co 1 0 -alkylthio, phenylthio, phenyl and phenoxy, C 1 C 10 o-haloalkoxycarbonyl, C 2 -Co 10 -alkenylcarbonyl, C 2 -Co 10 -alkenyloxycarbonyl, C 2 -Co 10 -haloalkenyloxycarbonyl, C 1 -Co 10 -alkylcarbonyl, C4-C1o 15 haloalkylcarbonyl, hydroxy-Cl-Clo-alkyl, C 1 -C 1 0 -alkoxy- C 1 -Co 10 -alkyl, halo Cl-Co-alkoxy-Cl-Clo-alkyl, C 1 -Co 10 -alkoxycarbonyl-C-Co 0 -alkyl, halo-C 1 -Co 10 alkoxycarbonyl-C-Clo-alkyl R 7 R 8 N-CO-, benzoyl (C 6 H 5 -CO-), C3-C1o cycloalkylcarbonyl, R 6 a-CO - , wherein R 6 a is C 1 -C 4 -alkoxycarbonyl, phenoxy, naphthyl or a 5- or 6-membered heterocyclic radical with 1 to 4 20 heteroatoms which are selected, independently of one another, from O, N and S, it being possible for phenoxy, naphthyl and the 5- or 6-membered heterocyclic radical to be unsubstituted or substituted by 1, 2, 3, 4 or 5 substituents R a as defined above, and benzyl wherein benzyl may be substituted by 1, 2, 3, 4 or 5 substituents Rb as defined above; 25 R 7 , R 8 are selected independently of one another from H, C 1 -Clo-alkyl, C 1 -Co 10 haloalkyl, C 3 -Cl 10 -cycloalkyl, C 3 -Co 10 -halocycloalkyl, C 2 -Co 10 -alkenyl, C2-C1o haloalkenyl, C 2 -Co 10 -alkynyl, C 3 -Co 10 -haloalkynyl, phenyl, benzoyl, naphthyl or benzyl wherein the phenyl ring in the aforementioned four radicals may be 30 substituted by 1, 2, 3, 4 or 5 substituents which are selected, independently of one another, from halogen, cyano, nitro, C 1 -Co 10 -alkyl, Cl-Clo-haloalkyl, C 3 -Co 10 -cycloalkyl, C 3 -Co 10 -halocycloalkyl, C 2 -Co 10 -alkenyl, C 2 -Co 10 -haloalkenyl, Cl-Co 10 -alkoxy, C 1 -Co 10 -haloalkoxy, Cl-Co 10 -alkylthio, Cl-Co 10 -haloalkylthio, Cj C 10 -alkylsulfonyl, C 1 -Co 10 -haloalkylsulfonyl, hydroxy, CI-CIo-alkoxycarbonyl, 35 Cl-Co 10 -haloalkoxycarbonyl, C 2 -Co 10 -alkenyloxycarbonyl, C 2 -Co 1 0 haloalkenyloxycarbonyl, C 1 -C, 0 -alkylcarbonyl and C-Co 10 -haloalkylcarbonyl; R 9 is hydrogen, C 1 -Clo-alkyl, Cl-Clo-haloalkyl, C 3 -Co 10 -cycloalkyl, C3-Co0 halocycloalkyl, C 2 -Co 10 -alkenyl, C 2 -Co 10 -haloalkenyl, C 2 -Co 10 -alkynyl, C3-Cio 40 haloalkynyl, C 1 -Co-haloalkylsulfonyl, C 1 -Co 10 -alkylcarbonyl, C-Cjo- WO 2006/058730 PCT/EP2005/012787 123 haloalkylcarbonyl, R 7 R 8 N-CO-, phenyl, benzoyl, naphthyl or benzyl, wherein the phenyl ring in the aforementioned four radicals may be substituted by 1, 2, 3, 4 or 5 substituents Rb; and 5 R 1 0 is hydrogen or has one of the meanings given for Rc; R 11 , R 1 2 are selected independently of one another from H, Cl-Co 10 -alkyl, Cj-Co haloalkyl, C 3 -Co 10 -cycloalkyl, C 3 -Co 10 -halocycloalkyl, C2-Clo -alkenyl, C2-Co10 haloalkenyl, C 2 -Co 10 -alkynyl and C 3 -Co 10 -haloalkynyl, C 1 -Co 10 -alkoxy, C1-Clo 10 haloalkoxy, Cl-Co 10 -alkylthio, C 1 -Co 10 -haloalkylthio, hydroxy-C-C 1 0 -alkyl, Cj Co 10 -alkoxy-C 1 -Co 0 -alkyl, halo-C 1 -Co 10 -alkoxy-C 1 -Co 0 -alkyl, C-Co0 alkoxycarbonyl-C 1 -Co 0 -alkyl, halo-C0 1 -Co 10 -alkoxycarbonyl-C-Clo-alkyl, one of the radicals R 1 " or R 12 may also be Cl-Co 10 -alkylsulfonyl, C1-Cjo haloalkylsulfonyl, C 1 -Co 10 -alkoxycarbonyl, C 1 -C 1 0 -haloalkoxycarbonyl, C2 15 C 10 -alkenyloxycarbonyl, C 2 -Co 10 -haloalkenyloxycarbonyl, Cj-Cjo alkylcarbonyl, C 1 -Co 10 -haloalkylcarbonyl or R 7 R 8 N-CO-. R 1 3 is hydrogen, cyano, C 1 -Co 10 -alkyl, C 1 -Co 10 -haloalkyl, C 3 -Co-cycloalkyl, C3C10 halocycloalkyl, C 2 -Co 10 -alkenyl, C 2 -Co 10 -haloalkenyl, C 2 -C 1 0 -alkynyl, C'3-Clo 20 haloalkynyl, Cl-Co 10 -haloalkylsulfonyl, Cl-Co 10 -alkylcarbonyl, C1-C1o haloalkylcarbonyl, R 7 R 8 N-CO-, phenyl or benzyl, wherein phenyl and benzyl may be substituted by 1, 2, 3, 4 or 5 substituents Rb; except for a compound of formula I, wherein A and Ar are unsubstituted phenyl, 25 Q is a single bond, X is C=O and R', R 2 , R 3 , R 5 and R 6 are hydrogen.
2. The compound as claimed in claim 1, wherein A is a cyclic radical selected from phenyl and a 5- or 6-membered 30 heterocyclic radical with 1 to 4 heteroatoms which are selected, independently of one another, from O, N and S, and where the cyclic radical may have 1, 2, 3, 4 or 5 substituents R a which are selected, independently of one another, from halogen, cyano, nitro, Cl-Co-alkyl, Cj C 1 0 -haloalkyl, C 3 -Clo 10 -cycloalkyl, C 3 -C 0 lo-halocycloalkyl, C 2 -Co 10 -alkenyl, C2 35 C 1 0 -haloalkenyl, C 2 -Co 10 -alkynyl, C 3 -Co 10 -haloalkynyl, Cl-Co 10 -alkoxy, Cl-Co haloalkoxy, C2-Clo -alkenyloxy, C2-Clo -haloalkenyloxy, C 2 -Co 10 -alkynyloxy, C 3 -Co 10 -haloalkynyloxy, C 1 -Co 10 -alkylthio, Cl-Clo-haloalkylthio, Cj-Cjo alkylsulfinyl, C 1 -Co 10 -haloalkylsulfinyl, Cl-Co 10 -alkylsulfonyl, Cj-Cjo haloalkylsulfonyl, hydroxy, NR 7 R 8 , C-Co 10 -alkoxycarbonyl, C1-C1o 40 haloalkoxycarbonyl, C 2 -Co 10 -alkenyloxycarbonyl, C2-Clo- WO 2006/058730 PCT/EP2005/012787 124 haloalkenyloxycarbonyl, Cl-Clo-alkylcarbonyl, Cl-Clo-haloalkylcarbonyl, R 7 R 8 N-CO-, phenyl, benzyl and phenoxy, wherein phenyl, benzyl and phenoxy may be substituted by 1, 2, 3, 4 or 5 substituents Rb which are selected, independently of one another, from halogen, cyano, nitro, C 1 -Co 10 5 alkyl, C 1 -Co 10 -haloalkyl, C 3 -Co 10 -cycloalkyl, C 3 -Co 10 -halocycloalkyl, C 2 -C 1 0 alkenyl, C 2 -Co 10 -haloalkenyl, C 2 -Co 10 -alkynyl, C 3 -Co 10 -haloalkynyl, C1-Clo alkoxy, Cl-Co 10 -haloalkoxy, C 2 -Co 10 -alkenyloxy, C 2 -Co 10 -haloalkenyloxy, C2 C1 0 -alkynyloxy, C3-Clo -haloalkynyloxy, C 1 -Co 10 -alkylthio, C-Co 10 -haloalkylthio, C 1 -Co 10 -alkylsulfinyl, C-Co 10 -haloalkylsulfinyl, C 1 -Co 10 -alkylsulfonyl, C1-Co 10 haloalkylsulfonyl, hydroxy, NR 7 R 8 , C0 1 -Co 10 -alkoxycarbonyl, C-Co haloalkoxycarbonyl, C 2 -Co 1 0 -alkenyloxycarbonyl, C2-Co 0 haloalkenyloxycarbonyl, C 1 -Co 10 -alkylcarbonyl, C 1 -Co 10 -haloalkylcarbonyl and R 7 R 8 N-CO-, wherein two radicals R a which are bound to adjacent carbon atoms may form a CH=CH-CH=CH moiety or a O-CH 2 -O moiety, where in 15 these two moieties 1 or 2 hydrogen atoms may be replaced by a radical Rb as defined above; Ar is an aromatic radical selected from phenyl, naphthyl, pyridyl, pyrimidyl, furyl and thienyl, where the aromatic radical may carry 1, 2, 3, 4 or 5 20 substituents Rc which are selected, independently of one another, from halogen, cyano, nitro, C 1 -Co 10 -alkyl, C 1 -Co 10 -haloalkyl, C 3 -CI 10 -cycloalkyl, C3 C 1 0 -halocycloalkyl, C 2 -Co 10 -alkenyl, C2-Co 10 -haloalkenyl, C 2 -Co 1 0 -alkynyl, C3 Clo 0 -haloalkynyl, C 1 -Co 10 -alkoxy, C 1 -Co 10 -haloalkoxy, C 2 -Co 10 -alkenyloxy, C2 Clo 0 -alkynyloxy, C 3 -Clo-haloalkynyloxy, C-Co 10 -alkylthio, C 1 -Co 10 -haloalkylthio, 25 C0 1 -Co 0 -alkylsulfinyl, C-Co 10 -haloalkylsulfinyl, C 1 -Co 10 -alkylsulfonyl, C1-C1o haloalkylsulfonyl, hydroxy, NR 7 R 8 , Cl-Clo-alkoxycarbonyl, C-Co0 haloalkoxycarbonyl, C 2 -Co 10 -alkenyloxycarbonyl, C2-Co 10 -haloalkenyloxy carbonyl, C0 1 -Co 10 -alkylcarbonyl, Cl-Clo-haloalkylcarbonyl, R 7 R 8 N-CO-, phenyl, benzyl and phenoxy, wherein phenyl, benzyl and phenoxy may be 30 unsubstituted or substituted by 1, 2, 3, 4 or 5 substituents Rb as defined above; R' is selected from the group consisiting of H, C 1 -C 1 o-alkyl, C 1 -Co 10 -haloalkyl, C 3 -Co 10 -cycloalkyl, C 3 -Clo-halocycloalkyl, C 2 -Co 10 -alkenyl, C 2 -Co 10 -haloalkenyl, 35 C 2 -Co 10 -alkynyl and C 2 -Co 10 -haloalkynyl; R 6 is selected from the group consisiting of H, C-Co 0 -alkyl, which is optionally substituted by CN or NO 2 , C 1 -Clo-haloalkyl, C 3 -Co 10 -cycloalkyl, C3-ClO halocycloalkyl, C 2 -Co 10 -alkenyl, C 2 -Co 10 -haloalkenyl, C 2 -Co 10 -alkynyl, C2-Clo 40 haloalkynyl, C 1 -Co 10 -alkylsulfinyl, C-Co 10 -haloalkylsulfinyl, C-Co- WO 2006/058730 PCT/EP2005/012787 125 alkylsulfonyl, C 1 -Co 10 -haloalkylsulfonyl, C 1 -Co 10 -alkoxycarbonyl, C1-Co10 haloalkoxycarbonyl, C 2 -Co 1 0 -alkenyloxycarbonyl, C2-CIo haloalkenyloxycarbonyl, C 1 -Clo-alkylcarbonyl, Cl-Co 10 -haloalkylcarbonyl, hydroxy-Cl-Co 0 -alkyl, C-Clo-alkoxy- CI-Co 10 -alkyl, halo-C-Clo-alkoxy-C 5 C 1 0 -alkyl, C-Co-alkoxycarbonyl-C-Co 0 -alkyl, halo-C 1 -Co 10 -alkoxycarbonyl C 1 -Co 0 -alkyl R 7 R 8 N-CO- and benzyl wherein benzyl may be substituted by 1, 2, 3, 4 or 5 substituents Rb as defined above; and R 7 , R 8 are selected independently of one another from H, C-Co 0 -alkyl, Cj-Clo 10 haloalkyl, C 3 -Cl 10 -cycloalkyl, C 3 -Co 1 0 -halocycloalkyl, C2-Co 10 -alkenyl, C2-CIo haloalkenyl, C 2 -Co 10 -alkynyl, C 3 -Co 10 -haloalkynyl, phenyl or benzyl wherein phenyl and benzyl may be substituted by 1, 2, 3, 4 or 5 substituents which are selected, independently of one another, from halogen, cyano, nitro, Cs C 10 o-alkyl, C 1 -C 0 lo-haloalkyl, C 3 -Co 10 -cycloalkyl, C 3 -Co 10 -halocycloalkyl, C2-Clo 15 alkenyl, C2-Co 10 -haloalkenyl, C1-Co 10 -alkoxy, C01-C, 0 -haloalkoxy, C01-Co0 alkylthio, C-Co 10 -haloalkylthio, C0 1 -Co 0 -alkylsulfonyl, C0 1 -Co 0 -haloalkylsulfonyl, hydroxy, Cl-Cl-alkoxycarbonyl, C 1 -C0lo-haloalkoxycarbonyl, C2-Co10 alkenyloxycarbonyl, C2-Co 10 -haloalkenyloxycarbonyl, C 1 -Co 10 -alkylcarbonyl and C 1 -Co 10 -haloalkylcarbonyl. 20
3. The compound as claimed in claim 1, wherein Ar in formula I is phenyl, which is unsubstituted or substituted by 1, 2, 3 or 4 radicals Rc as defined above.
4. The compound as claimed in claim 1, wherein X in formula I is C=0. 25
5. The compound as claimed in claim 1, wherein A in formula I is a cyclic radical selected from phenyl, thienyl, furyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazoloyl, pyridyl, pyrimidinyl, pyrazinyl, and pyridazinyl and where the cyclic radical may be substituted by 1, 2 or 3 substituents R a as 30 defined above.
6. The compound as claimed in claim 1, wherein A in formula I is a cyclic radical selected from phenyl, thienyl, and pyridyl, where the cyclic radical may be substituted by 1, 2 or 3 substituents R a which are selected, independently of one 35 another, from halogen, C0 1 -C 4 -alkyl, C-C 4 -alkoxy, C-C 4 -haloalkoxy and C1-C4 haloalkyl.
7. The compound as claimed in claim 1, wherein A in formula I is 2-thienyl which may be substituted by 1, 2 or 3 substituents R a which are selected, independently WO 2006/058730 PCT/EP2005/012787 126 of one another, from halogen, CI-C 4 -alkyl, C 1 -C 4 -alkoxy, Cl-C 4 -haloalkoxy and C 1 -C 4 -haloalkyl.
8. The compound as claimed in claim 1, wherein Q in formula I is selected from a 5 single bond, -CH 2 -, O-CH 2 -, -S-CH 2 -, -O-CH(CH 3 )- and -S-CH(CH 3 )-.
9. The compound as claimed in claim 1, wherein Q and A together are Cl-C 0 -alkyl which may be substituted by 1 or 2 substituents selected from the group consisting of =0, OH and and C 1 -C 2 -alkoxy. 10
10. The compound of the general formula I as defined in claim 1 or a salt thereof, wherein R 1 is selected from the group consisting of hydrogen C-Clo-alkyl and C C1 0 -haloalkyl. 15
11. The compound as claimed in claim 1, wherein R 2 in formula I is selected from hydrogen, halogen and C0 1 -C 4 -alkyl.
12. The compound as claimed in claim 1, wherein R 3 in formula I is selected from hydrogen, halogen and C 1 -C 4 -alkyl. 20
13. The compound as claimed in claim 1, wherein R 3 in formula I is hydrogen.
14. The compound as claimed in claim 1, wherein R 4 is hydrogen or a radical R' as defined above. 25
15. The compound as claimed in claim 14, wherein Ar is phenyl, which is unsubstituted or substituted by 1, 2 or 3 radicals R c which are selected, independently of one another, from halogen, CN, C0 1 -C 4 -alkyl, C0 1 -C 4 -alkoxy, C1 C 4 -haloalkoxy and C-C 4 -haloalkyl. 30
16. The compound as claimed in claim 1, wherein R 4 together with R 2 is -0-.
17. The compound as claimed in claim 16 wherein Ar in formula I is phenyl, which is unsubstituted or which may carry 1, 2 or 3 radicals Rc which are selected, 35 independently of one another, from halogen, CN, Cl-C 4 -alkyl, C-C 4 -alkoxy, C C 4 -haloalkoxy and C 1 -C 4 -haloalkyl.
18. The compound as claimed in claim 1, wherein R 5 is selected from the group consisiting of H, C 1 -C 1 0 -alkyl, C 1 -Co 10 -haloalkyl, C3-C 10 -cycloalkyl, C3-Clo 40 halocycloalkyl, C2-Co 10 -alkenyl, C2-C 10 -haloalkenyl. WO 2006/058730 PCT/EP2005/012787 127
19. The compound as claimed in claim 1, wherein R 6 is hydrogen.
20. A composition for combating pests, selected from insects, arachnids and 5 nematodes, which comprises a pesticidally effective amount of at least one compound of the general formula I as defined in claim 1 and at least one inert carrier and/or at least one surfactant.
21. A method for combating pests, selected from insects, arachnids and nematodes, 10 which comprises contacting said pests, their habitat, breeding ground, food supply, plant, seed, soil, area, material or environment in which the animal pests are growing or may grow, or the materials, plants, seeds, soils, surfaces or spaces to be protected from an attack of or infestation by said pest, with a pesticidally effective amount of a compound of the general formula I as defined in 15 claim 1 or a salt thereof.
22. The method as claimed in claim 21, wherein the pests are insects.
23. A method for protecting crops from attack or infestation by pests, selected from 20 insects, arachnids and nematodes, the method comprising contacting a crop with a pesticidally effective amount of at least one compound of formula I as defined in claim 1 or with a salt thereof.
24. A method for protecting non-living materials from attack or infestation by pests, 25 selected from insects, arachnids and nematodes, the method comprising contacting the non-living material with a pesticidally effective amount of at least one compound of formula I as defined in claim 1 or with a salt thereof.
AU2005311429A 2004-12-01 2005-11-30 Hydrazide compounds for combating animal pests Abandoned AU2005311429A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US63227404P 2004-12-01 2004-12-01
US60/632,274 2004-12-01
PCT/EP2005/012787 WO2006058730A1 (en) 2004-12-01 2005-11-30 Hydrazide compounds for combating animal pests

Publications (1)

Publication Number Publication Date
AU2005311429A1 true AU2005311429A1 (en) 2006-06-08

Family

ID=35695526

Family Applications (1)

Application Number Title Priority Date Filing Date
AU2005311429A Abandoned AU2005311429A1 (en) 2004-12-01 2005-11-30 Hydrazide compounds for combating animal pests

Country Status (13)

Country Link
EP (1) EP1819224A1 (en)
JP (1) JP2008521856A (en)
KR (1) KR20070090898A (en)
CN (1) CN101068468A (en)
AP (1) AP2007004018A0 (en)
AU (1) AU2005311429A1 (en)
BR (1) BRPI0518725A2 (en)
CR (1) CR9137A (en)
IL (1) IL183198A0 (en)
MA (1) MA29112B1 (en)
MX (1) MX2007006538A (en)
WO (1) WO2006058730A1 (en)
ZA (1) ZA200704452B (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009059603A1 (en) 2007-11-05 2009-05-14 Vestergaard Frandsen Sa Room with two counter-resistant insecticidal objects
WO2012051708A1 (en) * 2010-10-21 2012-04-26 The University Of British Columbia Anti-bacterial pyruvate kinase modulator compounds, compositions, uses, and methods
CN103304441B (en) * 2013-06-09 2016-05-04 南京师范大学 A kind of O-methoxy phenylacetic acid class schiff bases and synthetic method and application
CN105837517B (en) * 2016-04-07 2019-08-06 浙江工业大学 A kind of hydrazide derivatives and the preparation method and application thereof of hydroxyl pyrimidine

Also Published As

Publication number Publication date
MX2007006538A (en) 2007-09-11
KR20070090898A (en) 2007-09-06
CR9137A (en) 2008-01-21
ZA200704452B (en) 2008-08-27
IL183198A0 (en) 2007-08-19
WO2006058730A1 (en) 2006-06-08
AP2007004018A0 (en) 2007-06-30
JP2008521856A (en) 2008-06-26
CN101068468A (en) 2007-11-07
EP1819224A1 (en) 2007-08-22
BRPI0518725A2 (en) 2008-12-02
MA29112B1 (en) 2007-12-03

Similar Documents

Publication Publication Date Title
US20090069317A1 (en) Insecticidal Methods Using 3-Amino-1,2-Benzisothiazole Derivatives
US20090069179A1 (en) Pyridin-4-ylmethylamides
US20070265231A1 (en) Hydrazide Compounds for Combating Animal Pests
JP2010516724A (en) 3-Amino-1,2-benzisothiazole compound II for controlling animal pests
CN101179936A (en) 1-(1,2-diphenyl-ethyl)-3-(2-hydroxyethyl)-thiourea compounds for combating animal pests
JP2009517369A (en) Cyanobenzene compounds for controlling animal pests
MX2007014138A (en) 1-(imidazolin-2-yl)amino-1,2-diphenylethane compounds for combating animal pests.
ES2335318T3 (en) 3-AMINO-1,2-BENZISOTIAZOL COMPOUNDS TO COMBAT ANIMAL PESTS.
AU2005311429A1 (en) Hydrazide compounds for combating animal pests
ES2339159T3 (en) ISOTIAZOLPIRIDIN-3-ILENAMINAS TO COMBAT ANIMAL PESTS.
ES2531448T3 (en) New compounds of hetaryl (thio) carboxamide to control invertebrate pests
EP1827102A1 (en) Azine compounds for combating animal pests
KR20060019558A (en) Hydrazone derivatives for combatting harmful insects and arachnids
CN101184737B (en) 1-(imidazolin-2-yl)amino-1,2-diphenylethane compounds for combating animal pests
ES2357969T3 (en) COMPOUNDS OF 1- (IMIDAZOLIN-2-IL) AMINO-1,2-DIFENYL ETHANE TO COMBAT ANIMAL PESTS.
WO2006097279A1 (en) Amidrazone compounds for combating animal pests
MX2008009989A (en) Pyridin-4 -ylmethylamides for combating pests

Legal Events

Date Code Title Description
MK1 Application lapsed section 142(2)(a) - no request for examination in relevant period