Substituted oxadiazoles for combating phytopathogenic fungi

Abstract

The present invention relates to novel oxadiazoles of the formula I or an N-oxide and/or their agriculturally useful salts and to their use for controlling phytopathogenic fungi, or to a method for combating phytopathogenic harmful fungi, which process comprises treating the fungi or the materials, plants, the soil or seeds to be protected against fungal attack, with an effective amount of at least one compound of the formula I, or an N-oxide, or an agriculturally acceptable salt thereof; and to mixtures comprising at least one such compound and at least one further pesticidally active substance selected from the group consisting of herbicides, safeners, fungicides, insecticides, and plant growth regulators; and to agrochemical compositions comprising at least one such compound and to agrochemical compositions further comprising seeds.

1 - 19 . (canceled) 
     
     
         20 . A compound of the formula I, 
       
         
           
           
               
               
           
         
       
       or an N-oxide, or an agriculturally acceptable salt thereof, 
       wherein
 A is phenyl or a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the aromatic heterocycle include besides carbon atoms 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein the cyclic groups A are unsubstituted or substituted by 1, 2, 3 or 4 identical or different groups R A ; wherein
 R A  is halogen, cyano, diC 1 -C 6 -alkylamino, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl or C 3 -C 8 -cycloalkoxy; and wherein any of the aliphatic or cyclic moieties are unsubstituted or substituted by 1, 2, 3 or 4 identical or different groups R a ; wherein
 R a  is halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio or C 3 -C 8 -cycloalkyl or C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl; 
 
 
 L is —C(═O)—, —C(═S)— or —S(═O) p —; 
 p is 0, 1 or 2; 
 R 1  and R 2  together with the nitrogen atom to which they are bound form a saturated or partially unsaturated 3- to 6-membered heterocycle, wherein the heterocycle includes beside one nitrogen atom and one or more carbon atoms no further heteroatoms or 1, 2 or 3 further heteroatoms independently selected from N, O and S as ring member atoms; and wherein one or two CH 2  groups of the heterocycle may be replaced by one or two groups independently selected from the group of C(═O) and C(═S); and wherein the heterocycle is unsubstituted or carries 1, 2, 3, 4 or up to the maximum possible number of identical or different groups R 1a ; wherein
 R 1a  is halogen, cyano, OH, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl, —NHSO 2 —C 1 -C 4 -alkyl, —(C═O)—C 1 -C 4 -alkyl, —C(═O)—C 1 -C 4 -alkoxy, C 1 -C 6 -alkylsulfonyl, hydroxyC 1 -C 4 -alkyl, —C(═O)—NH 2 , —C(═O)—NH(C 1 -C 4 -alkyl), C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, aminoC 1 -C 4 -alkyl, C 1 -C 4 -alkylamino-C 1 -C 4 -alkyl, diC 1 -C 4 -alkylamino-C 1 -C 4 -alkyl, aminocarbonyl-C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl; 
 
 R 3 , R 4  independently of each other are hydrogen, halogen, cyano or C 1 -C 6 -alkyl; or 
 R 3  and R 4  together with the carbon atom to which they are bound form a vinyl group or a saturated, monocyclic 3- to 5-membered heterocycle or carbocycle, wherein the heterocycle includes besides carbon atoms 1 or 2 heteroatoms independently selected from N, O and S as ring member atoms; and wherein the vinyl group, the heterocycle or the carbocycle is unsubstituted or carries 1, 2, 3, 4 or up to the maximum possible number of identical or different groups R 3a ; wherein R 3a  is halogen, cyano or C 1 -C 2 -alkyl. 
 
     
     
         21 . The compound of  claim 20 , wherein R 3  and R 4  independently of each other are hydrogen, fluorine or methyl. 
     
     
         22 . The compound of  claim 20 , wherein R 3  and R 4  are hydrogen. 
     
     
         23 . The compound of  claim 20 , wherein A is a phenyl ring or a thiophene ring. 
     
     
         24 . The compound of  claim 20 , wherein L is —C(═O)—. 
     
     
         25 . The compound of  claim 20 , wherein R 1  and R 2  together with the nitrogen atom to which they are bound form a saturated or partially unsaturated 3- to 6-membered heterocycle, wherein the heterocycle includes beside one nitrogen atom and one or more carbon atoms no further heteroatoms or one additional heteroatom selected from N, O and S as ring a member atom; and wherein the heterocycle is unsubstituted or carries 1, 2, 3, 4 or up to the maximum possible number of identical or different groups R 1a  as defined in claim  1 . 
     
     
         26 . The compound of  claim 20 , wherein R 1  and R 2  together with the nitrogen atom to which they are bound form a saturated monocyclic 3- or 4-membered heterocycle, wherein the heterocycle includes beside one nitrogen atom no further heteroatoms; and wherein the heterocycle is unsubstituted or carries 1, 2, 3, 4 or up to the maximum possible number of identical or different groups R 1a  as defined in claim  1 . 
     
     
         27 . An agrochemical composition, which comprises an auxiliary and at least one compound of the formula I of  claim 20 , or an N-oxide, or an agriculturally acceptable salt thereof. 
     
     
         28 . An agrochemical composition of  claim 27 , wherein the auxiliary is selected from the group consisting of anionic, cationic and nonionic surfactants. 
     
     
         29 . An agrochemical composition of  claim 27  further comprising seed, wherein the amount of the compound of the formula I, or an N-oxide, or an agriculturally acceptable salt thereof, is from 0.1 g to 10 kg per 100 kg of seed. 
     
     
         30 . A method for combating phytopathogenic harmful fungi, which process comprises treating the plants, the soil or seeds to be protected against fungal attack, with an effective amount of at least one compound of formula I of  claim 20 , or an N-oxide, or an agriculturally acceptable salt thereof.