Pesticidally active pyrazole derivatives
View Patent ↗The invention relates to compounds of formula (I) as defined herein, to processes for preparing them, to pesticidal, in particular insecticidal, acaricidal, molluscicidal and nematicidal compositions comprising them and to methods of using them to combat and control pests such as insect, acarine, mollusc and nematode pests.
1. A compound of formula (I)
Wherein
R 1 is selected from H, C 1 -C 6 -alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 3 -C 7 cycloalkyl-C 1 -C 3 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, aryl(C 0 -C 3 )-alkyl and heteroaryl(C 0 -C 3 )-alkyl, wherein each of C 1 -C 6 -alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 3 -C 7 cycloalkyl-C 1 -C 3 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, aryl(C 0 -C 3 )-alkyl and heteroaryl(C 0 -C 3 )-alkyl is unsubstituted or substituted with 1 to 7 substituents independently selected from halogen, cyano, C 1 -C 6 -alkoxy and C 1 -C 6 -alkoxycarbonyl;
Q is selected from H, hydroxy, —C(═O)H, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 3 -C 7 heterocycloalkyl containing 1 to 4 heteroatoms, C 3 -C 7 cycloalkyl-C 1 -C 3 -alkyl, C 1 -C 3 -alkyl-C 3 -C 7 cycloalkyl, aryl(C 0 -C 3 )-alkyl, heteroaryl(C 0 -C 3 )-alkyl, N—C 1 -C 6 -alkylamino, N—C 1 -C 6 -alkylcarbonylamino and N,N-di (C 1 -C 6 -alkyl)amino, wherein each of C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 3 -C 7 heterocycloalkyl containing 1 to 4 heteroatoms, C 3 -C 7 cycloalkyl-C 1 -C 3 -alkyl, C 1 -C 3 -alkyl-C 3 -C 7 cycloalkyl, aryl(C 0 -C 3 )-alkyl, heteroaryl(C 0 -C 3 )-alkyl, N—C 1 -C 6 -alkylamino, N—C 1 -C 6 -alkylcarbonylamino and N,N-di (C 1 -C 6 -alkyl)amino is unsubstituted or substituted with 1 to 7 substituents independently selected from halogen, hydroxyl, nitro, amino, cyano, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, —C(═O)OH, C 1 -C 6 -alkylcarbamoyl, —C(═O)NH 2 , —C(═S)NH 2 , C 3 -C 6 -cycloalkylcarbamoyl and phenyl;
W is O or S;
T is a 5-membered heteroaryl of formula
wherein
indicates the bond to the group
and * indicates the bond to the pyrazole ring;
D 1 is selected from CR 6a , N, NR 6b , O and S;
D 2 is selected from CR 7a , N, NR 7b , O and S;
D 3 is C or N;
D 4 is selected from CR 8a , N, NR 8b , O and S;
D 5 is C or N;
with the proviso that at least one of D 1 , D 2 , D 3 , D 4 and D 5 is selected from N, O and S, that no more than one of D 1 , D 2 and D 4 is O or S, that no more than four of D 1 , D 2 , D 3 , D 4 and D 5 are N, and that D 3 and D 5 are not N at the same time;
R 6a , R 7a and R 8a are independently selected from H, halogen, cyano, nitro, amino, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 3 -C 7 cycloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl and C 1 -C 6 -alkylsulfonyl, wherein each of C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 3 -C 7 cycloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl and C 1 -C 6 -alkylsulfonyl is unsubstituted or substituted with 1 to 7 halogen;
R 6b , R 7b and R 8b are independently selected from H and C 1 -C 6 -alkyl, wherein C 1 -C 6 -alkyl is unsubstituted or substituted with 1 to 7 halogen;
Z 1 is selected from C 1 -C 6 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxy, C 3 -C 7 heterocycloalkyl containing 1 to 4 heteroatoms, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, wherein each C 1 -C 6 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxy, C 3 -C 7 heterocycloalkyl containing 1 to 4 heteroatoms, C 1 -C 6 -alkyl and C 3 -C 6 -cycloalkyl is unsubstituted or substituted with 1 to 7 substituents independently selected from halogen, hydroxy, nitro, amino, cyano, C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, —C(═O)OH, C 1 -C 6 -alkylcarbamoyl, C 3 -C 6 -cycloalkylcarbamoyl and phenyl;
Z 2 is selected from H, halogen, cyano, nitro, amino, C 1 -C 6 -alkoxy, C 3 -C 7 -heterocycloalkyl containing 1 to 4 heteroatoms, C 3 -C 7 -cycloalkyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl and C 1 -C 6 -alkylsulfonyl, wherein each of C 1 -C 6 -alkoxy, C 3 -C 7 -heterocycloalkyl containing 1 to 4 heteroatoms, C 3 -C 7 -cycloalkyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl and C 1 -C 6 -alkylsulfonyl is unsubstituted or substituted with 1 to 7 substituents independently selected from halogen, hydroxy, nitro, amino, cyano, C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, —C(═O)OH, C 1 -C 6 -alkylcarbamoyl, C 3 -C 6 -cycloalkylcarbamoyl and phenyl;
Z 3 is selected from H, C 1 -C 6 -alkyl, C 1 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, aryl and heteroaryl, wherein each of C 1 -C 6 -alkyl, C 1 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, aryl and heteroaryl, is unsubstituted or substituted with 1 to 7 substituents independently selected from halogen, hydroxy, nitro, amino, cyano, C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, —C(═O)OH, C 1 -C 6 -alkylcarbamoyl, C 3 -C 6 -cycloalkylcarbamoyl and phenyl;
or an agrochemically acceptable salt or N-oxide thereof.
2. The compound of claim 1 , wherein T is selected from
wherein * indicates the bond to the pyrazole group.
3. The compound of claim 1 , wherein T is selected from
wherein * indicates the bond to the pyrazole group.
4. The compound of claim 1 , wherein
R 1 is H, methyl or ethyl;
Q is selected from 1-cyano-cyclopropyl, benzyl, cyclopropyl, 2-thienylmethyl, 1-carbamothioylcyclopropyl, 1-(C(═O)—NH 2 )-cyclopropyl, 1-(C(═S)—NH 2 )-cyclopropyl, 1-hydroxycarbonyl-cyclopropyl, pyrid-4-yl, 2,2,2-trifluorethyl, methyl sulfonyl, thietan-3-yl and 1-carbamoylcyclopropyl;
W is O;
if present, R 6a , R 7a and R 8a are independently selected from H, methyl, chloro, bromo, trifluoromethyl and trifluoromethoxy;
if present, R 6b , R 7b and R 8b are independently selected from H and methyl;
Z 1 is selected from methyl, ethyl, 1,1-dimethylethyl, difluoromethyl, trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trifluoromethyl, bromodichloromethyl, 1-fluoroethyl, 1-fluoro-1-methylethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,2,2,2-tetrafluoroethyl, 1-chloro-1,2,2,2-tetrafluoroethyl, 2,2,2-trichloroethyl, 2-chloro-2,2-difluoroethyl, 1,1-difluoroethyl, pentafluoroethyl, 3,3,3,2,1,1-hexafluoropropyloxy, 2-trifluoromethoxy-2,1,1-trifluoroethoxy, heptafluoro-n-propyl, heptafluoro-isopropyl, nonafluoro-n-butyl, cyclopropyl, 1-chlorocyclopropyl, 1-fluorocyclopropyl, 1-bromocyclopropyl, 1-cyano-cyclopropyl, 1-trifluoromethyl-cyclopropyl, cyclobutyl and 2,2-difluoro-1-methyl-cyclopropyl;
Z 2 is selected from H, halogen, cyano, nitro, amino, methyl, ethyl, 1,1-dimethylethyl, difluoromethyl, trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trifluoromethyl, bromodichloromethyl, 1-fluoroethyl, 1-fluoro-1-methylethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,2,2,2-tetrafluoroethyl, 1-chlor-1,2,2,2-tetrafluoroethyl, 2,2,2-trichloroethyl, 2-chloro-2,2-difluoroethyl, 1,1-difluoroethyl, difluoromethoxy, trifluoromethoxy, pentafluoroethyl, heptafluoro-n-propyl, heptafluoro-isopropyl, nonafluoro-n-butyl, methylsulfanyl, methylsulfinyl, methyl sulfonyl, ethylthio, ethylsulfinyl, ethylsulfonyl, trifluoromethylsulfanyl, trifluoromethylsulfinyl, trifluoromethylsulfonyl, chloro-difluoromethylsulfanyl, chloro-difluoromethylsulfinyl, chloro-difluoromethylsulfonyl, dichloro-fluoromethylsulfanyl, dichloro-fluoromethylsulfinyl, dichloro-fluoromethylsulfonyl; and
Z 3 is selected from H, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, ethenyl, 1-propenyl, 1-propynyl, 1-butynyl, difluoromethyl, trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trifluoromethyl, 1-fluoroethyl, 1 fluoro-1-methylethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,5-dichlorophenyl, 3,4-dichlorophenyl, 2,6-dichlorophenyl 2,6-dichloro-4-trifluoromethylphenyl, 3-chloro-5-trifluormethylpyridin-2-yl, 4-NO 2 -phenyl and 3-chloro-pyridin-2-yl.
5. The compound of claim 1 , wherein
R 1 is H, methyl or ethyl;
Q is selected from cyclopropyl, 1-cyano-cyclopropyl, 1-C(═O)—NH 2 -cyclopropyl, 1-C(═S)—NH 2 -cyclopropyl, 1-(trifluoromethyl)-cyclopropyl, 2-fluoro-cyclopropyl and 2-(trifluoromethyl)-cyclopropyl;
W is O;
if present, R 6a , R 7a and R 8a are independently selected from H, chloro, bromo, fluoro, methyl, trifluoromethyl, methoxy and cyano;
if present, R 6b , R 7b and R 8b are independently selected from H and methyl;
Z 1 is selected from C 1 -C 6 -alkoxy, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkoxy and C 1 -C 6 -haloalkyl wherein each C 1 -C 6 -alkoxy, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkoxy and C 1 -C 6 -haloalkyl is unsubstituted or substituted with 1 to 7 substituents independently selected from halogen, C 1 -C 6 -alkoxy and C 1 -C 6 -haloalkoxy;
Z 2 is selected from C 1 -C 6 -alkoxy, C 1 -C 6 -alkyl, wherein each of C 1 -C 6 -alkoxy and C 1 -C 6 -alkyl is unsubstituted or substituted with 1 to 7 substituents independently selected from halogen;
Z 3 is selected from methyl, ethyl, cylopropyl, n-propyl and H.
6. The compound of claim 1 , wherein
R 1 is H, methyl or ethyl;
Q is selected from cyclopropyl, 1-cyano-cyclopropyl, 2-fluoro-cyclopropyl and 2-(trifluoromethyl)-cyclopropyl;
W is O;
if present, R 6a , R 7a , R 8a , R 6b , R 7b and R 8b are independently selected from H, chloro, fluoro, methyl, trifluoromethyl, methoxy and cyano;
Z 1 is CF 2 CF 3 , —OCF 2 CFHCF 3 or —OCF 2 CFHOCF 3 ;
Z 2 is CF 3 , or OCF 2 H;
Z 3 is methyl.
7. A pesticidal composition, which comprises at least one compound according to claim 1 , or an agrochemically acceptable salt or N-oxide thereof, as active ingredient and at least one auxiliary.
8. The composition according to claim 7 , which further comprises one or more other insecticidally, acaricidally, nematicidally and/or fungicidally active agents.
9. A method for controlling pests, which comprises applying a composition according to claim 7 to the pests or their environment with the exception of a method for treatment of the human or animal body by surgery or therapy and diagnostic methods practised on the human or animal body.
10. A method for the protection of plant propagation material from the attack by pests, which comprises treating the propagation material or the site, where the propagation material is planted, with a composition according to claim 7 .
11. A coated plant propagation material, wherein the coating of the plant propagation material comprises a compound as defined in claim 1 .
12. A compound of formula (II)
wherein
T is a 5-membered heteroaryl of formula
wherein
indicates the bond to the group
and * indicates the bond to the pyrazole ring;
D 1 is selected from CR 6 a, N, NR 6b , O and S;
D 2 is selected from CR 7 a, N, NR 7b , O and S;
D 3 is C or N;
D 4 is selected from CR 8a , N, NR 8b , O and S;
D 5 is C or N;
with the proviso that at least one of D 1 , D 2 , D 3 , D 4 and D 5 is selected from N, O and S, that no more than one of D 1 , D 2 and D 4 is O or S, that no more than four of D 1 , D 2 , D 3 , D 4 and D 5 are N, and that D 3 and D 5 are not N at the same time;
R 6a , R 7a and R 8a are independently selected from H, halogen, cyano, nitro, amino, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 3 -C 7 cycloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl and C 1 -C 6 -alkylsulfonyl, wherein each of C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 3 -C 7 cycloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl and C 1 -C 6 -alkylsulfonyl is unsubstituted or substituted with 1 to 7 halogen;
R 6b , R 7b and R 8b are independently selected from H and C 1 -C 6 -alkyl, wherein C 1 -C 6 -alkyl is unsubstituted or substituted with 1 to 7 halogen;
Z 1 is selected from C 1 -C 6 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxy, C 3 -C 7 heterocycloalkyl containing 1 to 4 heteroatoms, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, wherein each C 1 -C 6 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxy, C 3 -C 7 heterocycloalkyl containing 1 to 4 heteroatoms, C 1 -C 6 -alkyl and C 3 -C 6 -cycloalkyl is unsubstituted or substituted with 1 to 7 substituents independently selected from halogen, hydroxy, nitro, amino, cyano, C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, —C(═O)OH, C 1 -C 6 -alkylcarbamoyl, C 3 -C 6 -cycloalkylcarbamoyl and phenyl;
Z 2 is selected from H, halogen, cyano, nitro, amino, C 1 -C 6 -alkoxy, C 3 -C 7 -heterocycloalkyl containing 1 to 4 heteroatoms, C 3 -C 7 -cycloalkyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl and C 1 -C 6 -alkylsulfonyl, wherein each of C 1 -C 6 -alkoxy, C 3 -C 7 -heterocycloalkyl containing 1 to 4 heteroatoms, C 3 -C 7 -cycloalkyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl and C 1 -C 6 -alkylsulfonyl is unsubstituted or substituted with 1 to 7 substituents independently selected from halogen, hydroxy, nitro, amino, cyano, C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, —C(═O)OH, C 1 -C 6 -alkylcarbamoyl, C 3 -C 6 -cycloalkylcarbamoyl and phenyl;
Z 3 is selected from H, C 1 -C 6 -alkyl, C 1 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, aryl and heteroaryl, wherein each of C 1 -C 6 -alkyl, C 1 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, aryl and heteroaryl, is unsubstituted or substituted with 1 to 7 substituents independently selected from halogen, hydroxy, nitro, amino, cyano, C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, —C(═O)OH, C 1 -C 6 -alkylcarbamoyl, C 3 -C 6 -cycloalkylcarbamoyl and phenyl; and
R is selected from OH, C 1 -C 6 alkoxy, Cl, F and Br.
13. A compound of formula (III)
wherein
T is a 5-membered heteroaryl of formula
wherein
indicates the bond to the group
and * indicates the bond to the pyrazole ring;
D 1 is selected from CR 6 a, N, NR 6b , O and S;
D 2 is selected from CR 7 a, N, NR 7b , O and S;
D 3 is C or N;
D 4 is selected from CR 8a , N, NR 8b , O and S;
D 5 is C or N;
with the proviso that at least one of D 1 , D 2 , D 3 , D 4 and D 5 is selected from N, O and S, that no more than one of D 1 , D 2 and D 4 is O or S, that no more than four of D 1 , D 2 , D 3 , D 4 and D 5 are N, and that D 3 and D 5 are not N at the same time;
R 6a , R 7a and R 8a are independently selected from H, halogen, cyano, nitro, amino, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 3 -C 7 cycloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl and C 1 -C 6 -alkylsulfonyl, wherein each of C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 3 -C 7 cycloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl and C 1 -C 6 -alkylsulfonyl is unsubstituted or substituted with 1 to 7 halogen;
R 6b , R 7b and R 8b are independently selected from H and C 1 -C 6 -alkyl, wherein C 1 -C 6 -alkyl is unsubstituted or substituted with 1 to 7 halogen;
Z 1 is selected from C 1 -C 6 -alkoxy, 4-alkoxy-C 1 -C 4 -alkoxy, C 3 -C 7 heterocycloalkyl containing 1 to 4 heteroatoms, C 3 -C 6 -cycloalkyl, wherein each C 1 -C 6 -alkoxy, 4-alkoxy-C 1 -C 4 -alkoxy, C 3 -C 7 heterocycloalkyl containing 1 to 4 heteroatoms, C 1 -C 6 -alkyl and C 3 -C 6 -cycloalkyl is unsubstituted or substituted with 1 to 7 substituents independently selected from halogen, hydroxy, nitro, amino, cyano, C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, —C(═O)OH, C 1 -C 6 -alkylcarbamoyl, C 3 -C 6 -cycloalkylcarbamoyl and phenyl;
Z 2 is selected from H, halogen, cyano, nitro, amino, C 1 -C 6 -alkoxy, C 3 -C 7 -heterocycloalkyl containing 1 to 4 heteroatoms, C 3 -C 7 -cycloalkyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl and C 1 -C 6 -alkylsulfonyl, wherein each of C 1 -C 6 -alkoxy, C 3 -C 7 -heterocycloalkyl containing 1 to 4 heteroatoms, C 3 -C 7 -cycloalkyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl and C 1 -C 6 -alkylsulfonyl is unsubstituted or substituted with 1 to 7 substituents independently selected from halogen, hydroxy, nitro, amino, cyano, C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, —C(═O)OH, C 1 -C 6 -alkylcarbamoyl, C 3 -C 6 -cycloalkylcarbamoyl and phenyl;
Z 3 is selected from H, C 1 -C 6 -alkyl, C 1 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, aryl and heteroaryl, wherein each of C 1 -C 6 -alkyl, C 1 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, aryl and heteroaryl, is unsubstituted or substituted with 1 to 7 substituents independently selected from halogen, hydroxy, nitro, amino, cyano, C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, —C(═O)OH, C 1 -C 6 -alkylcarbamoyl, C 3 -C 6 -cycloalkylcarbamoyl and phenyl; and
X B is a suitable leaving group.
14. The compound of claim 13 , wherein X B is Cl, Br, F and I.