5-substituted-alkylaminopyrazole derivatives as pesticides
The invention relates to the use for the control of pests, of a compound which is a 5-substituted-alkylaminopyrazole derivative of formula (I) or a salt thereof: wherein the various symbols are as defined in the description, to novel 5-substituted-alkylaminopyrazole derivatives and pesticidal compositions thereof, and to processes for their preparation.
1. 5-Substituted-alkylaminopyrazole derivatives of formula (I)
or pesticidally acceptable salts thereof, wherein:
R 1 is CN;
W is C-halogen or C—CH 3 ;
R 2 is hydrogen, halogen or CH 3 ;
R 3 is (C 1 -C 3 )-haloalkyl, (C 1 -C 3 )-haloalkoxy or S(O) p —(C 1 -C 3 )-haloalkyl;
R 4 is (C 1 -C 6 )-alkenyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl, (C 3 -C 7 )-cycloalkyl, CO(CH 2 ) q —R 7 , CO—(CH 2 ) q R 9 , —CO—(C 1 -C 4 )-alkyl-(C 1 -C 6 )-alkoxy, —CO 2 —(CH 2 ) q R 7 , —CO 2 R 8 , —CO 2 —(CH 2 ) q —R 9 , —CO 2 —(C 3 -C 7 )-cycloalkyl, —CO 2 —(C 1 -C 4 ) -alkyl-(C 3 -C 7 )-cycloalkyl, —CO 2 —(C 3 -C 6 )-alkenyl, —CO 2 —(C 3 -C 6 )-alkynyl, CONR 10 R 11 , —CH 2 R 7 , —CH 2 R 9 , OR 7 , OR 8 or OR 9 ; or (C 1 -C 6 )-alkyl which is substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, (C 3 -C 7 )-cycloalkyl, S(O) p R 8 , CO 2 —(C 1 -C 6 )-alkyl, —O(C═O)—(C 1 -C 6 )-alkyl, NR 10 COR 12 , NR 10 R 11 , CONR 10 R 11 , SO 2 NR 10 R 11 , OH, CN, NO 2 , OR 7 , NR 10 SO 2 R 8 , COR 8 and OR 9 ;
A is (C 2 -C 12 )-alkylene and (C 1 -C 12 )-haloalkylene in which 2, 3 or 4 adjacent carbon atoms optionally form part of a (C 3 -C 8 )-cycloalkyl ring which is unsubstituted or substituted by one or more radicals selected from the group consisting of (C 1 -C 6 )-alkyl and halogen; or is (C 1 -C 12 )-alkylene or (C 1 -C 12 )-haloalkylene in which last two mentioned groups a methylene moiety is replaced by a group selected from —C(═O)—, —C(═NH)—, —O—, —S— and —NR 15 —, with the proviso that the replacing group is not bonded to the adjacent O or N atom; or is (C 2 -C 12 )-alkenylene or (C 2 -C 12 )-haloalkenylene;
R 5 is (C 3 -C 6 )-alkenyl, (C 3 -C 6 )-haloalkenyl, (C 3 -C 6 )-alkynyl, (C 3 -C 6 )-haloalkynyl, (C 3 -C 7 ) -cycloalkyl, —(CH 2 ) q R 7 , —(CH 2 ) q R 9 or NR 10 R 11 ; 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 3 -C 6 )-alkenyloxy, (C 3 -C 6 )-haloalkenyloxy, (C 3 -C 6 ) -alkynyloxy, (C 3 -C 6 )-haloalkynyloxy, (C 3 -C 7 )-cycloalkyl, S(O) p R 8 , CN, NO 2 , OH, COR 10 , NR 10 COR 12 , NR 10 SO 2 R 8 , CONR 10 R 11 , NR 10 R 11 , S(O) p R 7 , S(O) p R 9 , OR 7 , OR 9 and CO 2 R 10 ; or when A is (C 2 -C 12 )-alkylene or (C 1 -C 12 )-haloalkylene and R 5 is (C 1 -C 6 )-alkyl unsubstituted or substituted by one or more halogen radicals, one or more of the carbon atoms of R 5 may, together with O and one or more of the carbon atoms of A, form a 5- or 6-membered ring;
R 6 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 or (C 2 -C 6 )-haloalkynyl;
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 8 , COR 11 , COR 13 , CONR 10 R 11 , SO 2 NR 10 OR 11 , NR 10 R 11 , OH, SO 3 H and (C 1 -C 6 )-alkylideneimino;
R 8 is (C 1 -C 6 )-alkyl or (C 1 -C 6 )-haloalkyl;
R 9 is heterocyclyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy, NO 2 , CN, CO 2 (C 1 -C 6 )-alkyl, S(O) p R 8 , OH and oxo;
R 10 and R 12 are each independently H, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 3 -C 6 )-alkenyl, (C 3 -C 6 ) -haloalkenyl, (C 3 -C 6 )-alkynyl, (C 3 -C 6 )-haloalkynyl, (C 3 -C 6 )-cycloalkyl, —(C 1 -C 6 )-alkyl-(C 3 -C 6 ) -cycloalkyl, —(CH 2 ) q R 13 or —(CH 2 ) q R 9 ; or
R 10 and R 11 and/or R 10 and R 12 each together with the respective attached N atom form a five- or six-membered saturated ring which optionally contains an additional hetero atom in the ring which is selected from O, S and N, the ring being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 6 )-alkyl and (C 1 -C 6 )-haloalkyl;
R 11 and R 14 are each independently H, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 3 -C 6 )-cycloalkyl or —(C 1 -C 6 )-alkyl-(C 3 -C 6 )-cycloalkyl;
R 13 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 8 and NR 11 R 14 ;
R 15 is R 11 or —(CH 2 ) q R 13 ;
n and p are each independently zero, one or two;
q is zero or one; and
each heterocyclyl in the above-mentioned radicals is independently a heterocyclic radical having 3 to 7 ring atoms and 1, 2 or 3 hetero atoms in the ring selected from the group consisting of N, O and S.
2. 5-Substituted-alkylaminopyrazole derivatives of formula (I) as in claim 1 , or pesticidally acceptable salts thereof, wherein:
R 1 is CN;
W is C-halogen or C—CH 3 ;
R 2 is hydrogen, halogen or CH 3 ;
R 3 is (C 1 -C 3 )-haloalkyl, (C 1 -C 3 )-haloalkoxy or S(O) p —(C 1 -C 3 )-haloalkyl;
R 4 is (C 1 -C 6 )-alkyl or COR 8 ;
A is (C 2 -C 12 )-alkylene and (C 1 -C 12 )-haloalkylene in which 2, 3 or 4 adjacent carbon atoms optionally form part of a (C 3 -C 8 )-cycloalkyl ring which is unsubstituted or substituted by one or more radicals selected from the group consisting of (C 1 -C 6 )-alkyl and halogen; or is (C 1 -C 12 )-alkylene or (C 1 -C 12 )-haloalkylene in which last two mentioned groups a methylene moiety is replaced by a group selected from —C(═O)—, —C(═NH)—, —O—, —S— and —NR 15 —, with the proviso that the replacing group is not bonded to the adjacent O or N atom; or is (C 2 -C 12 )-alkenylene or (C 2 -C 12 )-haloalkenylene;
R 5 is (C 3 -C 6 )-alkenyl, (C 3 -C 6 )-haloalkenyl, (C 3 -C 6 )-alkynyl, (C 3 -C 6 )-haloalkynyl, (C 3 -C 7 ) -cycloalkyl, —(CH 2 ) q R 7 , —(CH 2 ) q R 9 or NR 10 R 11 ; or is (C 1 -C 6 )-alkyl substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 6 )-alkoxy, (C 1 -C 6 ) -haloalkoxy, (C 3 -C 6 )-alkenyloxy, (C 3 -C 6 )-haloalkenyloxy, (C 3 -C 6 )-alkynyloxy, (C 3 -C 6 ) -haloalkynyloxy, (C 3 -C 7 )-cycloalkyl, S(O) p R 8 , CN, NO 2 , OH, COR 10 , NR 10 COR 12 , NR 10 SO 2 R 8 , CONR 10 R 11 , NR 10 R 11 , S(O) p R 7 , S(O) p R 9 , OR 7 , OR 9 and CO 2 R 10 ; or when A is (C 2 -C 12 )-alkylene or (C 1 -C 12 )-haloalkylene and R 5 is (C 1 -C 6 )-alkyl unsubstituted or substituted by one or more halogen radicals, one or more of the carbon atoms of R 5 may, together with O and one or more of the carbon atoms of A, form a 5- or 6-membered ring;
R 6 is (C 1 -C 6 )-haloalkyl;
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 8 , COR 11 , COR 13 , CONR 10 R 11 , SO 2 NR 10 R 11 , NR 10 R 11 , OH, SO 3 H and (C 1 -C 6 )-alkylideneimino;
R 8 is (C 1 -C 6 )-alkyl or (C 1 -C 6 )-haloalkyl;
R 9 is heterocyclyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy, NO 2 , CN, CO 2 (C 1 -C 6 )-alkyl, S(O) p R 8 , OH and oxo;
R 10 and R 12 are each independently H, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 3 -C 6 )-alkenyl, (C 3 -C 6 ) -haloalkenyl, (C 3 -C 6 )-alkynyl, (C 3 -C 6 )-haloalkynyl, (C 3 -C 6 )-cycloalkyl, —(C 1 -C 6 )-alkyl-(C 3 -C 6 ) -cycloalkyl, —(CH 2 ) q R 13 or —(CH 2 ) q R 9 ; or
R 10 and R 11 and/or R 10 and R 12 each together with the respective attached N atom form a five- or six-membered saturated ring which optionally contains an additional hetero atom in the ring which is selected from O, S and N, the ring being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 6 )-alkyl and (C 1 -C 6 )-haloalkyl;
R 11 and R 14 are each independently H, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 3 -C 6 )-cycloalkyl or —(C 1 -C 6 )-alkyl-(C 3 -C 6 )-cycloalkyl;
R 13 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 8 and NR 11 R 14 ;
R 15 is R 11 or —(CH 2 ) q R 13 ;
n and p are each independently zero, one or two;
q is zero or one; and
each heterocyclyl in the above-mentioned radicals is independently a heterocyclic radical having 3 to 7 ring atoms and 1, 2 or 3 hetero atoms in the ring selected from the group consisting of N, O and S.
3. 5-Substituted-alkylaminopyrazole derivatives of formula (I), as in claim 1 , or pesticidally acceptable salts thereof, wherein:
R 1 is CN; R 2 is chlorine; R 3 is CF 3 or OCF 3 ; W is C—Cl; R 4 is (C 1 -C 6 )-alkyl; R 5 is (C 1 -C 6 )-alkyl; R 6 is CF 3 ; A is (C 2 -C 3 )-alkylene and n is zero, one or two.
4. A pesticidal composition comprising a compound of formula (I) or a pesticidally acceptable salt thereof as defined in any one of claims 1 to 3 , with a pesticidally acceptable diluent or carrier and/or surface active agent.
5. 5-substituted-alkylaminopyrazole derivatives of formula (I) as in claim 1 , or pesticidally acceptable salts thereof, wherein:
R 1 is CN; R 2 is chlorine; R 3 is CF 3 or OCF 3 ; W is C—Cl; R 4 is CO 2 CH 2 CH 3 ; R 5 is (C 1 -C 6 )-alkyl;
R 6 is CF 3 ; A is (C 2 -C 3 )-alkylene and n is zero, one or two.
6. 5-substituted-alkylaminopyrazole derivatives of formula (I) as in claim 1 , or pesticidally acceptable salts thereof, wherein:
R 1 is CN; R 2 is chlorine; R 3 is CF 3 or OCF 3 ; W is C—Cl; R 4 is Ch 2 OCH 2 CH 3 ; R 5 is (C 1 -C 6 )-alkyl;
R 6 is CF 3 ; A is (C 2 -C 3 )-alkylene and n is zero, one or two.