Method for controlling ppo resistant weeds

Abstract

A method for controlling PPO resistant weeds, wherein compounds of formula (I) wherein the variables are defined as given in the description and claims; are applied to the PPO inhibitor herbicide resistant weed, parts of it or its propagation material.

1 . A method for controlling the growth of PPO resistant weeds, which comprises contacting such weeds, parts of it, its propagation material or its habitat with compounds of formula (I) 
       
         
           
           
               
               
           
         
         wherein 
         R 1  is H, F or C 1 ; 
         R 2  is F, Cl, Br, CN, C(O)NH 2  or C(S)NH; 
         R 3  is H, F, Cl, CH 3  or OCH 3 ; 
         R 4  is H, CN, CH 3 , CF 3 , OCH 3 , OC 2 H 5 , SCH 3 , SC 2 H 5 , (CO)OC 2 H 5  or CH 2 R 6 ,
 wherein R 6  is F, Cl, OCH 3 , SCH 3 , SC 2 H 5 , CH 2 F, CH 2 Br or CH 2 OH; 
 
         R 5  is (C 1 -C 6 -alkyl)amino, (C 1 -C 6 -dialkyl)amino, (NH)OR 7 , OH, OR 8  or SR 8 ,
 wherein R 7  is CH 3 , C 2 H 5  or phenyl; and
 R 8  is C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 2 -C 6 -cyanoalkyl, C 1 -C 4 -alkoxy-carbonyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkyl-carbonyl-amino, C 1 -C 6 -alkylsulfinyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkyl-sulfonyl-C 1 -C 6 -alkyl, C 1 -C 6 -dialkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkyl-carbonyloxy-C 1 -C 6 -alkyl, phenyl-carbonyl-C 1 -C 6 -alkyl, tri(C 1 -C 3 -alkyl)-silyl-C 1 -C 6 -alkyl, tri(C 1 -C 3 -alkyl)-silyl-C 2 -C 6 -alkenyl, tri(C 1 -C 3 -alkyl)-silyl-C 2 -C 6 -alkynyl, tri(C 1 -C 3 -alkyl)-silyl-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, dimethylamino, tetrahydropyranyl, tetrahydrofuranyl-C 1 -C 3 -alkyl, phenyl-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, phenyl-C 1 -C 3 -alkyl, pyridyl-C 1 -C 3 -alkyl, pyridyl or phenyl,
 wherein the pyridyl and phenyl rings independently of one another are substituted by one to five substituents selected from the group consisting of halogen, C 1 -C 3 -alkyl or C 1 -C 2 -haloalkyl; 
 
 C 3 -C 6 -cycloalkyl or C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl,
 wherein the cycloalkyl rings independently of one another are unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C 1 -C 3 -alkyl and C 1 -C 2 -haloalkyl; 
 
 
 
         X is O, S, S(O) or S(O) 2 ; 
         Y is N or CH; and 
         Z is O, S, S(O) or S(O) 2 ; 
         wherein the PPO resistant weeds are weeds, that are resistant to PPO-inhibiting herbicides except the compounds of formula (I). 
       
     
     
         2 . The method according to  claim 1 , wherein the PPO resistant weeds are resistant to at least one PPO-inhibiting herbicide selected from azafenidin and flumioxazin. 
     
     
         3 . The method according to  claim 1 , wherein the PPO resistant weeds are resistant to at least one PPO-inhibiting herbicide selected from fomesafen and lactofen. 
     
     
         4 . The method according to any of  claims 1  to  3 , wherein the PPO resistant weeds are not controlled by the application rate of 200 g/ha or lower of at least one PPO-inhibiting herbicide except the compound of formula (I). 
     
     
         5 . The method according to any of  claims 1  to  4 , wherein the PPO resistant weeds are selected from the group consisting of  Acalypha  ssp.,  Amaranthus  ssp.,  Ambrosia  ssp.,  Avena  ssp.,  Conyza  ssp.,  Descurainia  ssp.,  Euphorbia  ssp. and  Senecio  ssp. 
     
     
         6 . The method according to any of  claims 1  to  4 , wherein the PPO resistant weeds are selected from the group consisting of Asian copperleaf, smooth pigweed, Palmer amaranth, redroot pigweed, tall/common waterhemp, common ragweed, wild oat, flixweed, wild poinsettia and Eastern groundsel. 
     
     
         7 . The method according to any of  claims 1  to  3 , wherein the PPO resistant weeds are selected from the group consisting of Palmer amaranth, tall/common waterhemp and common ragweed. 
     
     
         8 . The method according to any of  claims 1  to  7 , wherein the PPO resistant weeds contain a ΔG210 or R98L mutation in the Protox enzyme conferring resistance to PPO-inhibiting herbicides. 
     
     
         9 . The method according to any of  claims 1  to  8 , wherein the compound of formula (I) is selected from the compounds of formulae (I).1 and (I.)4: 
       
         
           
           
               
               
           
         
       
     
     
         10 . The method according to any of  claims 1  to  9 , wherein a herbicidal composition comprising at least one compound of formula (I), and at least one further compound selected from herbicides B and/or safeners C is applied. 
     
     
         11 . The method according to  claim 10 , wherein the herbicide B is selected from the herbicides of class b1) to b15):
 b1) lipid biosynthesis inhibitors;   b2) acetolactate synthase inhibitors (ALS inhibitors);   b3) photosynthesis inhibitors;   b4) protoporphyrinogen-IX oxidase inhibitors (PPO inhibitors) other than the compounds of formula (I);   b5) bleacher herbicides;   b6) enolpyruvyl shikimate 3-phosphate synthase inhibitors (EPSP inhibitors);   b7) glutamine synthetase inhibitors;   b8) 7,8-dihydropteroate synthase inhibitors (DHP inhibitors);   b9) mitosis inhibitors;   b10) inhibitors of the synthesis of very long chain fatty acids (VLCFA inhibitors);   b11) cellulose biosynthesis inhibitors;   b12) decoupler herbicides;   b13) auxinic herbicides;   b14) auxin transport inhibitors; and   b15) other herbicides selected from the group consisting of bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, indaziflam, maleic hydrazide, mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide, methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine, triaziflam, tridiphane and 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (CAS 499223-49-3) and its salts and esters;   
       including their agriculturally acceptable salts or derivatives. 
     
     
         12 . The method according to any of  claims 1  to  11 , wherein an agrochemical composition comprising at least one compound of formula (I) and auxiliaries customary for formulating crop protection agents, and optionally at least one further compound selected from herbicides B and/or safeners C, is applied. 
     
     
         13 . The use of compounds of formula (I) as defined in  claims 1  or  9  for controlling PPO resistant weeds. 
     
     
         14 . The use of the composition as defined in  claims 10  or  11  for controlling PPO resistant weeds. 
     
     
         15 . Method for controlling PPO resistant weeds as claimed in any of  claims 1  to  12 , wherein the compound of formula (I) is applied in a locus where PPO tolerant crops are grown.