1-phenyl and 1-pyridylpyrazole derivatives and their use as pesticides
The invention relates to 1-(2,4,6-trisubstituted-phenyl)-5-amino-4-substituted-pyrazole derivatives of formula (I) or salts thereof wherein the various symbols are as defined in the description, to processes for their preparation, to compositions thereof, and to their use for the control of pests (including arthropods and helminths).
1. A compound of formula (I):
wherein:
R 1 is CN, CSNH 2 , C(═N—Z)—S(O) r Q, (C 1 -C 6 )-alkyl or (C 1 -C 6 )-haloalkyl;
W is C—Y;
R 2 is (C 1 -C 6 )-alkyl, halomethyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl or (C 3 -C 7 )-cycloalkyl;
R 3 is (C 1 -C 3 )-haloalkyl, (C 1 -C 3 )-haloalkoxy or SF 5 ;
R 4 is NR 5 R 6 , OH, H, halogen, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkyl, OCO—(C 1 -C 6 )-alkyl or S(O) m —(C 1 -C 6 )-alkyl;
R 5 is H, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl, (C 3 -C 7 )-cycloalkyl, CO 2 —(C 1 -C 6 )-alkyl, CO 2 —(C 3 -C 7 )-cycloalkyl, CO 2 —(C 1 -C 4 )-alkyl-(C 3 -C 7 )-cycloalkyl, CO 2 —(C 2 -C 6 )-alkenyl, CO 2 —(CH 2 ) q R 7 , CONR 8 R 9 , (CH 2 ) q R 7 , or (C 1 -C 6 )-alkyl unsubstituted or substituted by one or more R 11 radicals;
R 6 is H, (C 2 -C 6 )-alkynyl, CO 2 —(C 1 -C 6 )-alkyl, (C 3 -C 7 )-cycloalkyl or SO 2 R 12 ; or (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl which last two mentioned groups are unsubstituted or substituted by one or more R 11 radicals;
X is NR 6a R 7a , OH, or benzyloxy;
Y is NR 6a R 7a , OH, halogen, NO 2 or methyl;
R 6a is H, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 7 )-cycloalkyl or (C 1 -C 6 )-alkyl which last mentioned group is substituted by one or more R 11 or R 7 radicals;
R 7a is (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 7 )-cycloalkyl or (C 1 -C 6 )-alkyl which
last mentioned group is substituted by one or more R 11 or R 7 radicals; CHO, CO—(C 1 -C 6 )-alkyl, CO 2 (C 1 -C 6 )-alkyl or SO 2 (C 1 -C 6 )-alkyl, which last three mentioned groups are unsubstituted or substituted by one or more R 11 radicals;
R 7 is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )haloalkoxy, CN, NO 2 , S(O) p R 13 and NR 9 R 14 ;
R 8 is H, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 3 -C 7 )-cycloalkyl, (C 3 -C 7 )-cycloalkyl-(C 1 -C 4 )-alkyl, or (CH 2 ) q R 7 ;
R 9 and R 14 are each independently H, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 3 -C 7 )-cycloalkyl or (C 3 -C 7 )-cycloalkyl-(C 1 -C 4 )-alkyl;
R 11 is halogen, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, (C 3 -C 7 )-cycloalkyl, S(O) p R 13 , CO 2 —(C 1 -C 6 )-alkyl, O(C═O)—(C 1 -C 6 )-alkyl, CO—(C 1 -C 6 )-haloalkyl, NR 8 R 9 , CONR 8 R 9 , SO 2 NR 8 R 9 , OH, CN, NO 2 , OR 7 , NR 8 COR 14 , or NR 8 SO 2 R 13 ;
R 12 is (C 3 -C 7 )-cycloalkyl, (C 2 -C 6 )-alkenyl, or (C 2 -C 6 )-haloalkenyl or; or phenyl unsubstituted or substituted by one or more radicals selected from R 15 ; or is (C 1 -C 6 )-alkyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, (C 2 -C 6 )-alkenyloxy, (C 2 -C 6 )-haloalkenyloxy, (C 2 -C 6 )-alkynyloxy, (C 2 -C 6 )-haloalkynyloxy, (C 3 -C 7 )cycloalkyl, S(O) p R 7 , S(O) p R 13 , CN, NO 2 , OH, COR 8 , NR 8 COR 14 , NR 8 SO 2 R 13 , CONR 8 R 9 , NR 8 R 9 , OR 7 , R 16 , and CO 2 R 8 ;
R 13 is (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl or (C 3 -C 7 )-cycloalkyl;
R 15 is halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, CN, NO 2 , S(O) p R 13 , NR 8 R 9 , COR 13 , COR 7 , CONR 8 R 9 , SO 2 NR 8 R 9 , R 7 , SF 5 , OH, OR 7 , SO 3 H or (C 1 -C 6 )-alkylideneimino;
R 16 is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )haloalkoxy, CN, NO 2 , S(O) p R 13 , NR 8 R 9 , COR 13 , COR 7 , CONR 8 R 9 , SO 2 NR 8 R 9 , OH, SO 3 H and (C 1 -C 6 )-alkylideneimino;
Z is H, (C 1 -C 6 )-haloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (CH 2 ) q R 7 , COR 18 , CO 2 —(C 1 -C 6 )-alkyl and S(O) p R 18 ;
Q is (C 1 -C 6 )-alkyl or CH 2 R 7 ;
R 18 is (C 1 -C 6 )-alkyl or (C 1 -C 6 )-haloalkyl;
m, n, p and r are each independently zero, one or two;
q is zero or one;
or a pesticidally acceptable salt thereof.
2. A compound or a salt thereof as claimed in claim 1 wherein X is NR 6a R 7a or OH.
3. A compound or a salt thereof as claimed in claim 1 wherein Y is NR 6a R 7a , OH, or halogen.
4. A compound or a salt thereof as claimed in claim 1 , wherein:
R 1 is CN;
W is C—Y;
R 2 is (C 1 -C 3 )-alkyl or halomethyl;
R 3 is (C 1 -C 3 )-haloalkyl, (C 1 -C 3 )-haloalkoxy or SF 5 ;
R 4 is NR 5 R 6 , OH, H, halogen, (C 1 -C 3 )-alkoxy, (C 1 -C 3 )-alkyl or OCO—(C 1 -C 3 )-alkyl;
R 5 is H, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-haloalkenyl, (C 2 -C 4 )-alkynyl, (C 2 -C 4 )-haloalkynyl, (C 3 -C 7 )-cycloalkyl, CO 2 —(C 1 -C 3 )-alkyl, CO 2 —(C 3 -C 7 )-cycloalkyl, CO 2 —(C 1 -C 3 )-alkyl-(C 3 -C 7 )-cycloalkyl, CO 2 —(C 2 -C 4 )-alkenyl, CO 2 —(CH 2 ) q R 7 , CONR 8 R 9 , (CH 2 ) q R 7 , or (C 1 -C 3 )-alkyl unsubstituted or substituted by one or more R 11 radicals;
R 6 is H, (C 2 -C 4 )-alkynyl, CO 2 —(C 1 -C 3 )-alkyl, (C 3 -C 7 )-cycloalkyl or SO 2 R 12 ; or (C 1 -C 3 )-alkyl, (C 2 -C 4 )-alkenyl or CO—(C 1 -C 3 )-alkyl which last three mentioned groups are unsubstituted or substituted by one or more R 11 radicals;
X is NR 6a R 7a , or OH;
Y is halogen or methyl;
R 6a is H, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl or (C 1 -C 6 )-alkyl which last mentioned group is substituted by one or more R 11 or R 7 radicals;
R 7a is (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl or (C 1 -C 6 )-alkyl which last mentioned group is substituted by one or more R 11 or R 7 radicals;
R 7 is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, (C 1 -C 3 )-alkoxy, (C 1 -C 3 )-haloalkoxy, CN, NO 2 and S(O) p R 13 ;
R 8 is H, (C 1 -C 3 )-haloalkyl, (C 3 -C 7 )-cycloalkyl, (C 3 -C 7 )-cycloalkyl-(C 1 -C 3 )-alkyl or (CH 2 ) q R 7 ; and
R 9 and R 14 are each independently H, (C 1 -C 3 )-haloalkyl, (C 3 -C 7 )-cycloalkyl or (C 3 -C 7 )-cycloalkyl-(C 1 -C 3 )-alkyl;
R 11 is halogen, (C 1 -C 3 )-alkoxy, (C 1 -C 3 )-haloalkoxy, (C 3 -C 7 )-cycloalkyl, S(O) p R 13 , CO 2 —(C 1 -C 3 )-alkyl, O(C═O)—(C 1 -C 3 )-alkyl, CO—(C 1 -C 3 )-alkyl, CO—(C 1 -C 3 )-haloalkyl, NR 8 R 9 , CONR 8 R 9 , SO 2 NR 8 R 9 , OH, CN, NO 2 , OR 7 , NR 8 COR 14 , or NR 8 SO 2 R 13 ;
R 12 is (C 3 -C 7 )-cycloalkyl, or (C 2 -C 4 )-alkenyl; or phenyl unsubstituted or substituted by one or more radicals selected from R 15 ; or is (C 1 -C 3 )-alkyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 3 )-alkoxy, (C 1 -C 3 )-haloalkoxy, (C 2 -C 4 )-alkenyloxy, (C 2 -C 4 )-alkynyloxy, (C 3 -C 7 )-cycloalkyl, S(O) p R 7 , S(O) p R 13 , CN, NO 2 , OH, COR 8 , NR 8 COR 14 , CONR 8 R 9 , NR 8 R 9 , OR 7 , R 16 , and CO 2 R 8 ;
R 13 is (C 1 -C 3 )-alkyl or (C 1 -C 3 )-haloalkyl;
R 15 is halogen, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, (C 1 -C 3 )-alkoxy, (C 1 -C 3 )-haloalkoxy, CN, NO 2 , S(O) p R 13 , NR 8 R 9 , COR 13 or OR 7 ;
R 16 is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, (C 1 -C 3 )-alkoxy, (C 1 -C 3 )haloalkoxy, CN, NO 2 , S(O) p R 13 , and NR 8 R 9 ;
Z is H, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-alkynyl, (CH 2 ) q R 7 , COR 18 , CO 2 —(C 1 -C 3 )-alkyl or S(O) p R 18 ;
Q is (C 1 -C 3 )-alkyl or CH 2 R 7 ;
R 18 is (C 1 -C 3 )-alkyl or (C 1 -C 3 )-haloalkyl;
m, n and p are each independently zero, one or two; and
q is zero or one.
5. A compound or a salt thereof as claimed in claim 1 wherein
W is C—Y;
X is NR 6a R 7a or OH; and
Y is NR 6a R 7a , OH, halogen, NO 2 or methyl.
6. A pesticidal composition for the control of arthropod or helminth pests comprising a pesticidally effective amount of a compound of formula (I) or a pesticidally acceptable salt thereof as defined in claim 1 , in association with a pesticidally acceptable diluent or carrier and/or surface active agent.
7. A method for controlling arthropod or helminth pests at a locus which comprises applying to said locus a pesticidally effective amount of a compound of formula (I) or a salt thereof as claimed in claim 1 .
8. A compound or salt thereof as claimed in claim 2 wherein Y is NR 6a R 7a , OH, halogen, NO 2 or methyl.
9. A method for controlling arthropod or helminth pests at a locus which comprises applying to said locus a pesticidally effective amount of a composition according to claim 6 .
10. A method for the control of arthropod or helminth parasites in or on an animal which comprises administering to said animal a pesticidally effective amount of a compound of formula (I) or a salt thereof as claimed in claim 1 .