Fungicidal substituted 2-[2-halogenalkyl-4-(phenoxy)-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds

Abstract

The present invention relates to substituted 2-[2-halogenalkyl-4-(phenoxy)-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds of formula I as defined in the description, and the N-oxides, and salts thereof, their preparation and intermediates for preparing them. The invention also relates to the use of these compounds for combating harmful fungi and seed coated with at least one such compound and also to compositions comprising at least one such compound.

1 - 13 . (canceled) 
     
     
         14 . A compound of formula I 
       
         
           
           
               
               
           
         
         wherein:
 R is CF 3 ; 
 R 1  is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkyl, phenyl, phenyl-C 1 -C 4 -alkyl, phenyl-C 2 -C 4 -alkenyl or phenyl-C 2 -C 4 -alkynyl; 
 R 2  is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, phenyl, phenyl-C 1 -C 4 -alkyl, phenyl-C 2 -C 4 -alkenyl or phenyl-C 2 -C 4 -alkynyl;
 wherein the aliphatic groups R 1  and/or R 2  may carry 1, 2, 3 or up to the maximum possible number of identical or different groups R a  which independently of one another are selected from the group consisting of halogen, CN, nitro, C 1 -C 4 -alkoxy and C 1 -C 4 -halogenalkoxy; 
 wherein the cycloalkyl and/or phenyl moieties of R 1  and/or R 2  may carry 1, 2, 3, 4, 5 or up to the maximum number of identical or different groups R b  which independently of one another are selected from the group consisting of halogen, CN, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenalkyl and C 1 -C 4 -halogenalkoxy; 
 
 R 3  is halogen, CN, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -halogenalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -halogenalkoxy 
 n is an integer and is 0, 1, 2 or 3; 
 R 4  is halogen, CN, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -halogenalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -halogenalkoxy 
 m is an integer and is 0, 1, 2, 3, 4 or 5; 
 and an N-oxide or an agriculturally acceptable salt thereof. 
 
       
     
     
         15 . The compound according to  claim 14 , wherein R 1  is hydrogen, C 1 -C 4 -alkyl, allyl, C 2 -C 6 -alkynyl, cyclopropyl, phenyl, benzyl, phenylethenyl or phenylethynyl. 
     
     
         16 . The compound according to  claim 14 , wherein R 2  is hydrogen, C 1 -C 4 -alkyl, allyl, propargyl or benzyl. 
     
     
         17 . The compound according to  claim 14 , wherein m is 1, 2 or 3 and R 4  is selected from F and Cl. 
     
     
         18 . The compound according to  claim 14 , wherein n=0, R 2  is hydrogen, R 4   m  is 4-Cl and R 1  is selected from the group consisting of H, CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , CH 2 C≡C—CH 3 , CH 2 C≡CH, isopropyl, cyclopropyl and CF 3 , and compounds wherein n=0, R 2  is CH 3 , R 4   m  is 4-Cl and R 1  is selected from H, CH 3 , CH 2 CH 3 , isopropyl and cyclopropyl, and the compound wherein n=0, R 2  is H, R 4   m  is 2,4-Cl 2  and R 1  is H, and the compound wherein n=0, R 2  is H, R 4   m  is 4-F and R 1  is CH 3 , and the compounds wherein n=0, R 1  is CH 3 , R 4   m  is 4-Cl and R 2  is selected from CH 2 CH 3 , and CH 2 CH═CH 2 , and the compounds wherein n=0, R 1  is methyl-propargyl, R 4   m  is 4-Cl and R 2  is selected from CH 2 CH 3 , and CH 2 C≡CH. 
     
     
         19 . A process for preparing compounds of formula I as defined in  claim 14 , which comprises reacting a compound of formula IIIa 
       
         
           
           
               
               
           
         
         in presence of a catalyst with isopropylmagnesium halide followed by a reaction with R 1 COCl; 
         reacting the resulting compound of formula VIII 
       
       
         
           
           
               
               
           
         
         under basic conditions with a compound of formula II 
       
       
         
           
           
               
               
           
         
         reacting the resulting compound of formula Va 
       
       
         
           
           
               
               
           
         
         with trimethylsulf(ox)onium halide; 
         reacting the resulting compound of formula IX 
       
       
         
           
           
               
               
           
         
         under basic conditions with 1H-1,2,4-triazole; 
         and optionally derivatizing the resulting compound of formula I.A 
       
       
         
           
           
               
               
           
         
         under basic conditions with R 2 -LG, wherein LG is a nucleophilically replaceable leaving group, to obtain compounds of formula I. 
       
     
     
         20 . A process for preparing compounds of formula I as defined in  claim 14 , which comprises reacting a compound of formula IX 
       
         
           
           
               
               
           
         
         under acidic conditions with R 2 —OH, 
         reacting the resulting compound of formula X 
       
       
         
           
           
               
               
           
         
         with a halogenating agent or sulfonating agent; 
         and reacting the resulting compound of formula XI 
       
       
         
           
           
               
               
           
         
         wherein LG is a nucleophilically replaceable leaving group with 1H-1,2,4-triazole to obtain compounds I. 
       
     
     
         21 . A compound of formulae IVa, Va, VI, VII or IX 
       
         
           
           
               
               
           
         
         wherein R 3 , R 4 , m and n and R 1 , if applicable, are as defined in  claim 14  and wherein X 1  is I or Br, and wherein R in formulae VI, Va, VII and IX is C 1 -C 2 -halogenalkyl, with the proviso that in formula Va if R 1  is hydrogen and R is CF 3  and n=0, R 4   m  is not 3-CF 3  or 3-CF 3 -4-Cl; and wherein in formula IVa R is selected from dichloromethyl, trichloromethyl, 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 and pentafluoroethyl, with the proviso that in formula IVa if X 1  is Br, R is CF 3  and n is 0, then m is not 0 and R 4   m  is not 4-Br, 3-CF 3 , 4-F or 2-Cl. 
       
     
     
         22 . An agrochemical composition comprising an auxiliary and at least one compound of formula I, as defined in  claim 14 , an N-oxide or an agriculturally acceptable salt thereof. 
     
     
         23 . The compositions according to  claim 22 , comprising additionally a further active substance. 
     
     
         24 . A method for combating phytopathogenic fungi, comprising: 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 formula I as defined in  claim 14 . 
     
     
         25 . The method of  claim 24 , wherein R 1  is hydrogen, C 1 -C 4 -alkyl, allyl, C 2 -C 6 -alkynyl, cyclopropyl, phenyl, benzyl, phenylethenyl or phenylethynyl. 
     
     
         26 . The method of  claim 24 , wherein R 2  is hydrogen, C 1 -C 4 -alkyl, allyl, propargyl or benzyl. 
     
     
         27 . The method of  claim 24 , wherein m is 1, 2 or 3 and R 4  is selected from F and Cl. 
     
     
         28 . The method of  claim 24 , wherein n=0, R 2  is hydrogen, R 4   m  is 4-Cl and R 1  is selected from the group consisting of H, CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , CH 2 C≡C—CH 3 , CH 2 C≡CH, isopropyl, cyclopropyl and CF 3 , and compounds wherein n=0, R 2  is CH 3 , R 4   m  is 4-Cl and R 1  is selected from H, CH 3 , CH 2 CH 3 , isopropyl and cyclopropyl, and the compound wherein n=0, R 2  is H, R 4   m  is 2,4-Cl 2  and R 1  is H, and the compound wherein n=0, R 2  is H, R 4   m  is 4-F and R 1  is CH 3 , and the compounds wherein n=0, R 1  is CH 3 , R 4   m  is 4-Cl and R 2  is selected from CH 2 CH 3 , and CH 2 CH═CH 2 , and the compounds wherein n=0, R 1  is methyl-propargyl, R 4   m  is 4-Cl and R 2  is selected from CH 2 CH 3 , and CH 2 C≡CH. 
     
     
         29 . Seed coated with at least one compound of formula I as defined in  claim 14 , in an amount of from 0.1 g to 10 kg per 100 kg of seed. 
     
     
         30 . The seed of  claim 29 , wherein R 1  is hydrogen, C 1 -C 4 -alkyl, allyl, C 2 -C 6 -alkynyl, cyclopropyl, phenyl, benzyl, phenylethenyl or phenylethynyl. 
     
     
         31 . The seed of  claim 29 , wherein R 2  is hydrogen, C 1 -C 4 -alkyl, allyl, propargyl or benzyl. 
     
     
         32 . The seed of  claim 29 , wherein m is 1, 2 or 3 and R 4  is selected from F and Cl. 
     
     
         33 . The seed of  claim 29 , wherein n=0, R 2  is hydrogen, R 4   m  is 4-Cl and R 1  is selected from the group consisting of H, CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , CH 2 C≡C—CH 3 , CH 2 C≡CH, isopropyl, cyclopropyl and CF 3 , and compounds wherein n=0, R 2  is CH 3 , R 4   m  is 4-Cl and R 1  is selected from H, CH 3 , CH 2 CH 3 , isopropyl and cyclopropyl, and the compound wherein n=0, R 2  is H, R 4   m  is 2,4-Cl 2  and R 1  is H, and the compound wherein n=0, R 2  is H, R 4   m  is 4-F and R 1  is CH 3 , and the compounds wherein n=0, R 1  is CH 3 , R 4   m  is 4-Cl and R 2  is selected from CH 2 CH 3 , and CH 2 CH═CH 2 , and the compounds wherein n=0, R 1  is methyl-propargyl, R 4   m  is 4-Cl and R 2  is selected from CH 2 CH 3 , and CH 2 C≡CH.