Substituted azines as pesticides

Patent metadata

Field	Value
Publication number	US-9357782-B2
Application number	US-201314418100-A
Country	US
Kind code	B2
Filing date	Aug 6, 2013
Priority date	Aug 8, 2012
Publication date	Jun 7, 2016
Grant date	Jun 7, 2016

Abstract

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.

First claim

The invention claimed is:

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.

Assignees

• Novartis Ag
• Novartis Tiergesundheit Ag

Inventors

• Gauvry Noelle
• Pautrat Francois

Classifications

• A61P33/10

  Anthelmintics · CPC title

• A61P33/14

  Ectoparasiticides, e.g. scabicides · CPC title

• A01N43/62

  three- or four-membered rings or rings with more than six members · CPC title

• C07D401/04 Primary

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07D401/14

  containing three or more hetero rings · CPC title