Herbicidal imidazole, pyrazole, thiazole and isothiazole derivatives

Claim 1

A compound of the formula: where R is H or CH 3 ; Q is R1 is H, C 1 -C 8 alkyl, C 3 -C 6 alkenyl, C 5 -C 6 cycloalkyl, C 5 -C 6 cycloalkenyl, C 3 -C 6 alkynyl, C 4 -C 7 cycloalkylalkyl, (R 17 CH) n C(O)R 16 , (R 17 CH) n CO 2 R 18 , (R 17 CH) n COSR 19 , (R 17 CH) n CONR 20 R 21 , (R 17 CH) n SO 2 NR 20 R 21 , (R 17 CH) n SO 2 R 22 , or C 1 -C 6 alkyl substituted either with a) 1-3 atoms of F, Br or Cl; or b) OR16; R 2 , R 3 and R 4 are independently H or CH 3 ; R 5 is H, C 1 -C 4 alkyl, -OR 6 , NO 2 , F, Cl, Br, CO 2 R 24 , SCO) m R 25 or SO 2 NR 20 R 21 ; R 6 is H, C 1 -C 4 alkyl, C 3 -C 4 alkenyl C 3 -C 4 alkynyl, CO 2 R 18 , SO 2 NR 20 R 21 , SO 2 R 22 or C 1 -C 4 alkyl substituted with a) 1-3 carbon atoms of F, Ci or Br; or b) OCH 3 ; R 7 is H or CH 3 ; R8 is H , C 1 -C 4 alkyl, -OR 16 , N0 2 , F, Cl, Br, C0 2 R 24 , S(O) m R 25 or SO 2 NR 20 R 21 ; R 9 is CH 3 or C 2 H 5 ; R 10 is H , C 1 -C 4 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, CO 2 R 24 , SO 2 NR 20 R 21 or SO 2 R 22 ; R 11 is H , C 1 -C 3 alkyl, F , Cl , Br, NO 2 , -OR 16 , CO 2 R 24 , S(O) m R 25 or SO 2 NR 20 R 21 ; R 12 is H or CH 3 ; R 13 and R 14 are independently H, C 1 -C 3 alkyl -OR 16 , F, Cl, B r, NO 2 , C0 2 R 24 , S(O) m R 25 or SO 2 NR 20 R 21 ; R 15 is H or CH 3 ; R 16 is C 1 -C 3 alkyl; R17 is H or CH 3 ; R 18 is C 1 -C 4 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, CH2CH2Cl or CH 2 CH 2 OCH 3 ; R 19 is C 1 -C 4 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl or CH 2 CH 2 OCH 3 ; R 20 and R 21 are independently CH 3 or C 2 H 5 ; R 22 is C 1 -C 3 alkyl or CF 3 ; R23 is H , Cl, Br, CH 3 , F, CF 3 , OCH 3 or N0 2 ; R 24 is C 1 -C 3 alkyl or allyl; R 25 is C 1 -C 3 alkyl; m is 0, 1 or 2; n is 0 or 1; R 26 is H, C 1 -C 3 alkyl or CH 3 C(0)NH; R 27 is H, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 alkylthio or C 1 -C 3 alkoxycarbonyl; R 28 is H, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkoxycarbonyl, NO 2 , Cl, Br or CF 3 ; R29 is H , Cl or C H 3 ; R 30 is H, Cl or CH 3 ; R 31 is Cl, C 1 -C 3 alkoxycarbonyl or C 1 -C 3 alkyl; A is X is CH 3 ), OCH 3 , Cl, F, OCF 2 H or SCF 2 H; Y is CH 3 , C 2 H 5 , OCH 3 , OC 2 H 5 , CH 2 OCH 3 , CH(OCN 3 ) 2 , OCH 2 CF 3 , OCF 3 , N H 2 , NHCH 3 , N(CH 3 ) 2 or GCF 2 T where G is 0 or S and T is H, CHC1F, CHBrF, CF 2 H or CHFCF 3 ; Z is CH or N; Y 1 is H, Cl, CH 3 , OCH 3 or OCF 2 H; X 2 is OCH 3 , CH 3 , CH 2 CH 3 , OCH 2 CH 3 , SCH 3 or SCH 2 CH 3 ; Y 2 is CH 3 , CH 2 CH 3 or CH 2 CF 3 ; X 3 is OCH 3 or CH 3 ; provided that, a) when Q is Q-7, Q-8, Q-9 or Q-10, then R is H; b) the total number of carbon atoms in R 1 is less than or equal to 8; c) if R 1 is other than C 1 -C 3 alkyl, then R 3 must be H; d) when R 5 is other than H, CH 3 , OCH 3 or N0 21 then R 6 is H or CH 3 ; e) when R 6 is CO 2 R 18 , SO 2 NR 20 R 21 or SO 2 R 22 , then R 5 is H, CH 3 , OCH 3 or NO 2 ; f) when R 10 is other than C 1 -C 3 alkyl, then R 11 is H, Cl, OCH 3 , N0 2 or CH 3 ; g) when either of R 13 or R 14 is CO 2 R 24 , S(O) m R 25 or SO 2 NR 20 R 21 , then the other is H, Cl, CH 3 , OCH 3 or NO 2 ; h ) R 29 and R 30 are not simultaneously Cl; i) when X is Cl or F, then Z is CH and Y is OCH 3 , NH 2 , NHCH 3 or N(CH 3 ) 2 ; j) when Q is Q-7, Q-8, Q-9 or Q-10, then A is A-1; X is CH 3 , OCH 3 or OCF 2 H, Y is CH 3 , OCH 3 , OC 2 H 5 , OCF 2 H or CH 2 OCH 3 ; and, k) when either X or Y is OCF 2 H, then Z is CH; and agriculturally suitable salts thereof.

Claim 13

A method for controlling the growth of undesired vegetation comprising applying to the locus of such vegetatibn an agriculturally effective amount of one or more compounds of .any of Claims 1-10.

Claim 14

A method for regulating the growth of plants which comprises applying to the locus of such plants an effective but substantially non-phytotoxic amount of a plant growth regulant selected from compounds of any of Claims 1 to 10.