Chemical compounds

Abstract

A compound of the formula I where W, X and Y are for example each CH; R 1 is H; R 2 is halogen; and R 6 is, for formula I, for example, OH, CN, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkenyloxy, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkynyloxy, optionally substituted C1 to C3-alkyl, or optionally substituted C1-C6-alkoxy, or R 6 is, for formula II, for example, CN, C3-C8-cycloalkyl, or optionally substituted C3-C6-alkyl; and/or salts thereof; and their use as pesticidal agents.

1 . A compound of the formula I 
       
         
           
           
               
               
           
         
         where 
         W is C—R 3 ; 
         X is C—R 4 ; 
         Y is C—R 5 ; 
         R 1  is hydrogen 
         R 1  is halogen; 
         R 3 , R 4  and R 5 , independently of each other, are H, halogen, cyano, nitro, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkyl, C3-C8-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, OD or aryl; where D is C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, or aryl; and where the aryl, whenever mentioned, independent of each other, may be unsubstituted, have one or more halogen atoms and/or carry 1, 2 or 3 substituents, independently of one another, selected from the group consisting of cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy; and 
         R 6  is OH, CN, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkenyloxy, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkynyloxy, C1-C3-alkyl, or C1-C6-alkoxy,
 wherein the C1-C3-alkyl radical and the C1-C6-alkoxy radical, independent of each other, may be unsubstituted, have one or more halogen atoms and/or may carry 1, 2 or 3 radicals, independently of one another, each selected from the group consisting of cyano, nitro, amino, OH, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylthio, (C1-C6-alkoxy)carbonyl, (C1-C6-alkyl)amino, di-(C1-C6-alkyl)amino, C1-C6-alkylcarbonyloxy, arylcarbonyloxy, aryl and heterocyclyl; the aryl group, independent of attachment, may be unsubstituted, have one or more halogen atoms and/or carry 1, 2 or 3 substituents, independently of one another, selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, cyano, and nitro; the heterocyclyl group is a 4-7 membered heterocycle, which may be saturated, partially unsaturated or aromatic, which may contain 1, 2, or 3 heteroatom and/or heteroatom group as ring members, independently of one another, selected from C(═O), O, S, and N and may be unsubstituted or substituted with one or two substituents selected from halogen, C1-C6-(halo)alkyl, and C1-C6-(halo)alkoxy; provided that the alkyl radical in the instance it is C2-alkyl is not substituted with a chlorine atom, or; 
 
       
       or a salt thereof. 
     
     
         2 . The compound according to  claim 1  wherein R 3 , R 4  and R 5 , independently of each other, are selected from H, halogen, C1-C6-alkoxy and C1-C6-alkyl. 
     
     
         3 . The compound according to  claim 2  wherein R6 is heterocyclyl-C1-C3-alkyl, wherein the heterocyclyl group is a saturated, partially unsaturated or aromatic 5 or 6 membered ring containing, as ring members, one or two heteroatoms selected, independently of one another, from N, O and S, which may be unsubstituted or substituted with one or two halogen substituents. 
     
     
         4 . The compound according to  claim 2  wherein R6 is C1-C3-alkyl. 
     
     
         5 . The compound according to  claim 2  wherein R6 is C1-alkyl. 
     
     
         6 . The compound according to  claim 1  wherein R 5  is halogen. 
     
     
         7 . The compound according to  claim 1  wherein R2 is fluoro. 
     
     
         8 . The compound according to  claim 1  wherein R2 is chloro. 
     
     
         9 . A composition comprising the compound of formula I as defined in  claim 1  and one or more formulation auxiliary. 
     
     
         10 . A composition comprising the compound of formula I as defined in  claim 1 , and one or more active ingredients, and optionally one or more formulation auxiliary. 
     
     
         11 . A method for controlling a pest in crop protection or for protecting a seed, a plant, parts of a plant and/or plant organs that grow at a later point in time against pest damage which comprises applying a compound of formula I as defined in  claim 1  or a composition thereof to the pest, to the plant, to the seed, to the part of a plant and/or plant organ and/or the environment of each thereof. 
     
     
         12 . A seed comprising a compound of formula I as defined in  claim 1 . 
     
     
         13 . A method for controlling a pest which comprises applying a compound as defined in  claim 1  to the pest, material for protection and/or environment thereof. 
     
     
         14 . The method according to  claim 13  wherein the material is selected from a raw material including wood, textile, floor covering and building material. 
     
     
         15 . The method according to  claim 13  wherein the pest is controlled against damaging stored goods. 
     
     
         16 . The method according to  claim 13  wherein the pest is controlled in the hygiene sector, especially the protection of humans, domestic animals and productive livestock. 
     
     
         17 . The compound according to  claim 2  wherein R6 is OH, CN, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkenyloxy, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkynyloxy, C1-C3-alkyl, or C1-C6-alkoxy,
 wherein (1) the C1-C3-alkyl radical is unsubstituted or may carry 1, 2 or 3 radicals, (2) the C1-C6-alkoxy radical is unsubstituted, has one or more halogen atoms and/or may carry 1, 2 or 3 radicals, and (3) each of the 1, 2 or 3 radicals, when present, is independently selected from the group consisting of cyano, nitro, amino, OH, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylthio, (C1-C6-alkyl)amino, di-(C1-C6-alkyl)amino, aryl and heterocyclyl; the aryl group, independent of attachment, may be unsubstituted, have one or more halogen atoms and/or carry 1, 2 or 3 substituents, independently of one another, selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, cyano, and nitro; and the heterocyclyl group is a 4-7 membered heterocycle, which may be saturated, partially unsaturated or aromatic, which may contain 1, 2, or 3 heteroatom and/or heteroatom group as ring members, independently of one another, selected from C(═O), O, S, and N and may be unsubstituted or substituted with one or two substituents selected from halogen, C1-C6-(halo)alkyl, and C1-C6-(halo)alkoxy. 
 
     
     
         18 . The compound according to  claim 8  wherein R6 is OH, CN, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkenyloxy, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkynyloxy, C1-C3-alkyl, or C1-C6-alkoxy,
 wherein (1) the C1-C3-alkyl radical is unsubstituted or may carry 1, 2 or 3 radicals, (2) the C1-C6-alkoxy radical is unsubstituted, has one or more halogen atoms and/or may carry 1, 2 or 3 radicals, and (3) each of the 1, 2 or 3 radicals, when present, is independently selected from the group consisting of cyano, nitro, amino, OH, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylthio, (C1-C6-alkyl)amino, di-(C1-C6-alkyl)amino, aryl and heterocyclyl; the aryl group, independent of attachment, may be unsubstituted, have one or more halogen atoms and/or carry 1, 2 or 3 substituents, independently of one another, selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, cyano, and nitro; and the heterocyclyl group is a 4-7 membered heterocycle, which may be saturated, partially unsaturated or aromatic, which may contain 1, 2, or 3 heteroatom and/or heteroatom group as ring members, independently of one another, selected from C(═O), O, S, and N and may be unsubstituted or substituted with one or two substituents selected from halogen, C1-C6-(halo)alkyl, and C1-C6-(halo)alkoxy.