Pyridazin-3-one derivatives, their use, and intermediates for their production

A compound of the formula:

• 130
• wherein R1 is C1-C3 haloalkyl;
• R2 and R3 are the same or different and are hydrogen, C1-C3 alkyl, C1-C3 haloalkyl, or C1-C3 alkoxy C1-C3 alkyl;
• and Q is [Q-1, [Q-2], [Q-3], [Q-4], or [Q-5] of the formula;
• 131
• wherein
• X is hydrogen or halogen;
• Y is halogen. nitro, cyano, or trifluoromethyl;
• Z1 is oxygen. sulfur, or NH;
• Z2 is oxygen or sulfur;
• n is 0 or 1;
• B is hydrogen, halogen, nitro, cyano, chlorosulfonyl, OR10. SR10, SO2—OR10, N(R11)R12, SO2N(R11)R12, NR11(COR13), NR11(SO2R14), N(SO2R14)—(SO2R15), N(SO2R14)(COR13), NHCOOR13, COOR10, CON(R11)R12, CSN(R11)R12, COR16,CR17═CR18COR16,CR17═CR18COOR3 CR17═CR8CON(R1)R12,CH2CH WCOOR13, CR2CHWCON(R11)R12, CR17═NOR33, CR17═NN(R11)R12, CR17(Z2-R34)2, OCO2R19, or OCOR19;
• R4 is hydrogen or C1-C3 alkyl;
• R5 is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 cycloalkylalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, cyano C1-C6 alkyl, C2-C8 alkoxyalkyl, C3-C8 alkoxyalkoxyalkyl, carboxy C1-C6 alkyl, (C1-C6 alkoxy)-carbonyl C1-C6 alkyl, {(C1-C4 alkoxy) C1-C4 alkoxy}carbonyl C1-C6 alkyl, (C3-C8 cycloalkoxy)carbonyl C1-C6 alkyl, CH2CON(R11)R12, CH2COON(R11)R12, CH(C1-C4 alkyl)CON(R11)R12, CH(C1-C4 alkyl)COON(R11)R12, C2-C8 alkylthioalkyl, or hydroxy C1-C6 alkyl;
• R6 is C1-C6 alkyl, C1-C6 haloalkyl, formyl, cyano, carboxyl, hydroxy C1-C6 alkyl, C1-C6 alkoxy C)—C6 alkyl, C1-C6 alkoxy C1-C6 alkoxy C1-C6 alkyl, (C1-C6 alkyl)carbonyloxy C1-C6 alkyl, (C1-C6 haloalkyl)carbonyloxy C1-C6 alkyl, (C1-C6 alkoxy)carbonyl, or (C1-C6 alkyl)carbonyl;
• R7 is hydrogen or C1-C6 alkyl;
• and
• R8 is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, hydroxy C1-C6 alkyl, C2-C8 alkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, (C1-C5 alkyl)carbonyloxy C1-C6 alkyl, (C1-C6 haloalkyl)carbonyloxy C1-C6 alkyl, carboxyl, carboxy C1-C6 alkyl, (C1-Cg alkoxy)-carbonyl, (C1-C6 haloalkoxy)carbonyl, (C3-C10 cycloalkoxy)carbonyl, (C3-C8 alkenyloxy)carbonyl. (C3-Cg alkynyloxy)carbonyl, aminocarbonyl, (C1-C6 alkyl)aminocarbonyl. di(C1-C6 alkyl)aminocarbonyl, (C1-C6 alkyl)aminocarbonyloxy C1-C6 alkyl, or di(C1-C6 alkyl)aminocarbonyloxy C1-C6 alkyl;
• wherein R10 is hydrogen, C1-C6 alkyl. C1-C6 haloalkyl, C3-C8 cycloalkyl, benzyl. C1-C6 alkenyl, C1-C6 haloalkenyl. C1-C6 alkynyl, C3-C6 haloalkynyl, cyano C1-C6 alkyl, C2-C8 alkylthioalkyl C2-C8 carboxy C1-C6 alkyl, (C1-C8 alkoxy)carbonyl C1-C6 alkyl, (C1-C6 haloalkoxy)carbonyl C1-C6 alkyl, {(C1-C4 alkoxy) C1-C4 alkoxy)carbonyl C1-C6 alkyl, (C3-C8 cycloalkoxy)carbonyl C1-C6 alkyl, (C1-C6 alkyl)carbonyl C1-C6 alkyl, (C1-C6 haloalkyl)carbonyl C1-C6 alkyl, {(C1-C4 alkoxy) C1-C4 alkyl}carbonyl C1-C6 alkyl, (C3-Cg cycloalkyl)carbonyl C1-C6 alkyl, CH2CON—(R11)R12, CH2COON(R11)R12, CH(C1-C4 alkyl)CON(R11 )R12, CH(C1-C4 alkyl)-COON(R11)R12, ((C2-C6 alkoxy)carbonyl C1-C6 alkyl]oxycarbonyl C1-C6 alkyl, or hydroxy C1-C6 alkyl;
• R11 and R12 are independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 alkynyl, cyano C1-C6 alkyl, C2-C8 alkoxyalkyl, C2-C8 alkylthioalkyl, carboxy C1-C6 alkyl, (C1-C6 alkoxy)carbonyl C1-C6 alkyl, (C3-C8 cycloalkoxy)-carbonyl C1-C6 alkyl, {(C1-C4 alkoxy) C1-C4 alkoxy}carbonyl C1-C6 alkyl, or R11 and R12 are combined together to form tetramethylene, pentamethylene, or ethyleneoxyethylene;
• R13 is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 cycloalkyl, or C3-C6 alkenyl;
• R14 and R15 are independently C1-C6 alkyl, C1-C6 haloalkyl, or phenyl optionally substituted with methyl or nitro;
• R16 is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C2-C8 alkoxyalkyl, or hydroxy C1-C6 alkyl;
• R17 and R18 are independently hydrogen or C1-C6 alkyl;
• R19 is C1-C6 alkyl;
• R33 is hydrogen, C1-C6 alkyl. C1-C6 haloalkyl, C3-C8 cycloalkyl. C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, cyano C1-C6 alkyl, or (C1-C6 alkoxy)carbonyl C1-C6 alkyl;
• R34 is C1-C6 alkyl, or two R34's are combined together to form (CH2)2 or (CH)3;
• and
• W is hydrogen, chlorine, or bromine.