Haloalkyl triazolinones and herbicidal use thereof

Claim 1

An herbicidal compound of the formula ##STR32## in which X 1 is F or Cl; Z is nitro or a group of the formula --OR, --CO--R 6 , --CH 2 CO--R 6 , or --CH(CH 3 )CO--R 6 ; R is alkyl of 1 to 6 carbon atoms which is unsubstituted or is substituted with cycloalkyl or 3 to 7 carbon atoms, cycloalkyl of 3 to 7 carbon atoms which is unsubstituted or is substituted with alkyl of 1 to 6 carbon atoms, alkoxyalkyl of 2 to 8 carbon atoms, cyanoalkyl of 2 to 7 carbon atoms, alkenyl of 2 to 5 carbon atoms, alkynyl of 2 to 5 carbon atoms, haloalkyl of 1 to 5 carbon atoms, haloalkenyl of 2 to 5 carbon atoms, haloalkynyl of 2 to 5 carbon atoms, alkylsulfonyl of 1 to 6 carbon atoms (wherein the alkyl moiety is unsubstituted or is substituted with F, Cl, CN, alkoxy or alkylthio of 1 to 4 carbon atoms, or alkylamino or dialkylamino in which each alkyl is of 1 to 4 carbon atoms), alkylaminosulfonyl or dialkylaminosulfonyl in which each alkyl is of 1 to 4 carbon atoms, alkylcarbonyl of 2 to 7 carbon atoms, or a group of the formula --C(R 3 ) (R 4 ) (CH 2 ) n --CO--Q 1 R 5 or --C(R 3 ) (R 4 ) (CH 2 ) n --CO--N(R 7 ) (R 8 ) in which n is 0 to 2; R 3 and R 4 are independently H, alkyl of 1 to 4 carbon atoms, or alkoxy of 1 to 4 carbon atoms; Q 1 is O or S; R 5 is H, alkyl of 1 to 6 carbon atoms, alkoxyalkyl or alkylthioalkyl of 2 to 6 carbon atoms, haloalkyl of 1 to 5 carbon atoms, alkenyl of 2 to 5 carbon atoms, cycloalkenyl of 5 to 7 carbon atoms which is unsubstituted or is substituted with alkyl of 1 to 4 carbon atoms, cyclohexenylalkyl of 6 to 10 carbon atoms, phenyl or benzyl (which may be ring-substituted with fluorine, chlorine, bromine, or alkyl, alkoxy, or alkylthio of 1 to 4 carbon atoms), cyanoalkyl of 2 to 7 carbon atoms, alkynyl of 2 to 5 carbon atoms, alkylideneamino of 1 to 6 carbon atoms which is unsubstituted or is substituted with cycloalkyl 3 to 7 carbon atoms, or cycloalkylideneamino of 5 to 7 carbon atoms, which is unsubstituted or is substituted with alkyl of 1 to 4 carbon atoms; R 6 is hydroxy, alkoxy or alkylthio of 1 to 6 carbon atoms, alkoxyalkoxy of 2 to 6 carbon atoms, amino, or alkylamino or dialkylamino wherein each alkyl is of 1 to 6 carbon atoms and is unsubstituted or is substituted with alkoxy of 1 to 4 carbon atoms; R 7 is H or alkyl of 1 to 6 carbon atoms; R 8 is R 5 or alkoxy of 1 to 6 carbon atoms, alkylthio of 1 to 6 carbon atoms, alkylsulfonyl of 1 to 6 carbon atoms, phenylsulfonyl, or phenylalkylsulfonyl of 1 to 3 alkyl carbon atoms; R 1 is alkyl of 1 to 4 carbon atoms or haloalkyl of 1 to 3 carbon atoms; and R 2 is fluoroalkyl of 1 to 4 carbon atoms.