Substituted azines as pesticides
View Patent ↗The invention relates to compounds of the general formula (I), wherein the variable have the meanings as indicated in the claims, or a physiologically acceptable salt thereof. The active ingredients have advantageous pesticidal properties. They are especially suitable for controlling endoparasites in warm-blooded animals.
1. The compound of formula Ia
wherein one of R 1 and R 1 ′ is H and the other one is H, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, or amino, N-mono- or N,N-di-C 1 -C 4 -alkylamino; x and y are each independently of the other 1, 2 or 3; R 2 and R 3 are each independently of the other halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkoxy, C 1 -C 2 -haloalkoxyl, C 1 -C 2 -alkylthio, C 1 -C 2 -haloalkylthio, C 1 -C 2 -alkylsulfonyl, halo-C 1 -C 2 -alkylsulfonyl, amino, N-mono- and N,N-di-C 1 -C 4 -alkylamino, aminosulfonyl and C 1 -C 2 -alkylaminosulfonyl; wherein, if x or y is 2 or 3, the two or three radicals R 2 or R 3 each may be same or different; L 1 is a radical of formula
wherein X 1 , X 2 and X 3 are each independently NH, N(C 1 -C 2 -alkyl) or O, Y is —CH 2 —, —NH—, —C(O)— or —S(O 2 )—, p″ is 0 or 1 r′ is 0, 1 or 2, r and s are each independently 1 or 2, s′ is an integer 0, 1 or 2; and A 3 is C 2 -C 4 -alkylene or C 3 -C 6 -cycloalkylene; and L 2 is a radical of formula
wherein Y is —CH 2 —, —NH—, —C(O)— or —S(O) 2 —, t is 0 or 1, and X 5 and X 6 are each independently O or NH or N(CH 3 ).
2. A compound according to claim 1 , wherein L 1 is a radical of formula (IIa′), (IIa″), (IIb′), (IIc′) or (IId′), one of s and r is 1 and the other one is 1 or 2, r′ is 0 or 1, s′ is 1 or 2, X 1 , X 2 and X 3 are each NH, p″ is 0, and A 4 is C 2 -C 4 -alkylene or C 5 -C 6 -cycloalkylene;
and L 2 is a radical of formula
wherein Y is —CH 2 —, —NH—, —C(O)— or —S(O) 2 —, t is 0 or 1, and X 5 and X 6 are each independently O or NH or N(CH 3 ).
3. A compound of formula (Ia) according to claim 1 , wherein R 1 is H and R 1 ′ is H, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, or amino, N-mono- or N,N-di-C 1 -C 4 -alkylamino;
x and y are each independently of the other 1 or 2;
R 2 and R 3 are each independently of the other halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkoxy, C 1 -C 2 -haloalkoxyl, C 1 -C 2 -alkylthio, C 1 -C 2 -haloalkylthio, C 1 -C 2 -alkylsulfonyl, halo-C 1 -C 2 -alkylsulfonyl, amino, N-mono- and N,N-di-C 1 -C 4 -alkylamino, aminosulfonyl and C 1 -C 2 -alkylaminosulfonyl; wherein, if x or y is 2, the two radicals R 2 or R 3 each may be same or different;
L 1 is a radical and
and
L 2 is a radical
or a physiologically acceptable salt thereof.
4. A compound according to claim 1 of formula
wherein Ar 1 is 4-CF 3 -phenyl, and Ar 2 is 4-nitro-3-CF 3 -phenyl, 4-cyano-3-CF 3 -phenyl, 3,4-di-CF 3 -phenyl, 4-CF 3 -3-fluorophenyl, 3-CF 3 -4-fluorophenyl, 4-nitrophenyl, 3- or 4-CF 3 -phenyl, 4-cyanophenyl, 4-OCF 3 -phenyl or 4-SCF 3 -phenyl.
5. Composition for the control of parasites, which contains as active ingredient at least one compound of formula (I) according to claim 4 , in addition to carriers and/or dispersants.
6. Method of controlling endoparasites, on warm-blooded animals, which comprises administering to the warm-blooded animals a veterinary effective amount of at least one compound of formula (I) according to claim 4 .
7. A compound according to claim 1 , wherein X 1 , X 2 and X 3 are each NH or N(CH 3 ).
8. A compound according to claim 3 , wherein R 1 ′ is H or methyl.
9. A compound according to claim 4 , wherein Ar 2 is 4-nitro-3-CF3-phenyl.