IP Library › Granted Patent US 10,836,732
Granted Patent B2
US 10,836,732 · App. 15/033,928 · Granted Nov 17, 2020

Compounds for combating arthropods

Inventors: Werner Hallenbach (Manheim, DE); Ulrich Goergens (Ratingen, DE); Andreas Turberg (Haan, DE); Kerstin Ilg (Cologne, DE); Sebastian Horstmann (Leverkusen, DE); Johannes Kobberling (Neuss, DE)
Assignee: BAYER ANIMAL HEALTH GMBH
C07D249/06A01N43/647C07D401/04C07D409/12
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Quick Facts
Patent No.
US 10,836,732
App. No.
15/033,928
Granted
Nov 17, 2020
Kind
B2
Abstract

The invention relates inter alia to novel compounds of the general formula (I) in which the A 1 -A 4 , T, W, Q, R 1 and B 1 -B 4 radicals are each as defined in the description. Also described are processes for preparing the compounds of the formula (I). The inventive compounds are especially suitable for controlling insects, arachnids and nematodes in agriculture, and ectoparasites in veterinary medicine.

Claims (190)

1. A compound of formula (Ie)

wherein

R 1 is H or methyl,

A 2 is CR 3 or N,

B 1 is CR 6 ,

B 5 is CR 10 ,

R 2 , R 3 , R 5 , R 7 , R 9 , and R 11 are each H,

R 4 is halogen,

R 6 is halogen, optionally fluorine-substituted methyl, or optionally fluorine-substituted methoxy,

R 8 is fluorine-substituted C 1 -C 4 -alkyl,

R 10 is halogen or methyl, and

Q is optionally cyano-substituted cyclopropyl,

and/or a salt, N-oxide and/or tautomeric form of a compound of formula (Ie).

2. The compound according to claim 1 , wherein R 1 is H.

3. The compound according to claim 1 , wherein

A 2 is C—H;

B 1 is C—Cl;

B 5 is C—Cl;

Q is cyclopropyl;

R 1 is H;

R 2 is H;

R 4 is Cl;

R 5 is H;

R 7 is H;

R 8 is i-C 3 F 7 ;

R 9 is H; and

R 11 is H.

4. The compound according to claim 1 , wherein

A 2 is C—H;

B 1 is C—Cl;

B 5 is C—Cl;

Q is 1-cyano-cyclopropyl;

R 1 is H;

R 2 is H;

R 4 is Cl;

R 5 is H;

R 7 is H;

R 8 is i-C 3 F 7 ;

R 9 is H; and

R 11 is H.

5. The compound according to claim 1 , wherein

A 2 is C—H;

B 1 is C—CH 3 ;

B 5 is C—CH 3 ;

Q is cyclopropyl;

R 1 is H;

R 2 is H;

R 4 is Cl;

R 5 is H;

R 7 is H;

R 8 is i-C 3 F 7 ;

R 9 is H; and

R 11 is H.

6. The compound according to claim 1 , wherein

A 2 is C—H;

B 1 is C—CH 3 ;

B 5 is C—CH 3 ;

Q is 1-cyano-cyclopropyl;

R 1 is H;

R 2 is H;

R 4 is Cl;

R 5 is H;

R 7 is H;

R 8 is i-C 3 F 7 ;

R 9 is H; and

R 11 is H.

7. The compound according to claim 1 , wherein

A 2 is N;

B 1 is C—CH 3 ;

B 5 is C—CH 3 ;

Q is cyclopropyl;

R 1 is H;

R 2 is H;

R 4 is Cl;

R 5 is H;

R 7 is H;

R 8 is i-C 3 F 7 ;

R 9 is H; and

R 11 is H.

8. The compound according to claim 1 , wherein

A 2 is N;

B 1 is C—CH 3 ;

B 5 is C—CH 3 ;

Q is 1-cyano-cyclopropyl;

R 1 is H;

R 2 is H;

R 4 is Cl;

R 5 is H;

R 7 is H;

R 8 is i-C 3 F 7 ;

R 9 is H; and

R 11 is H.

9. The compound according to claim 1 , wherein

A 2 is N;

B 1 is C—CF 3 ;

B 5 is C—CH 3 ;

Q is cyclopropyl;

R 1 is H;

R 2 is H;

R 4 is Cl;

R 5 is H;

R 7 is H;

R 8 is i-C 3 F 7 ;

R 9 is H; and

R 11 is H.

10. The compound according to claim 1 , wherein

A 2 is N;

B 1 is C—CF 3 ;

B 5 is C—CH 3 ;

Q is 1-cyano-cyclopropyl;

R 1 is H;

R 2 is H;

R 4 is Cl;

R 5 is H;

R 7 is H;

R 8 is i-C 3 F 7 ;

R 9 is H; and

R 11 is H.

11. The compound according to claim 1 , wherein

A 2 is N;

B 1 is C—CF 3 ;

B 5 is C—CH 3 ;

Q is cyclopropyl;

R 1 is CH 3 ;

R 2 is H;

R 4 is Cl;

R 5 is H;

R 7 is H;

R 8 is i-C 3 F 7 ;

R 9 is H; and

R 11 is H.

12. The compound according to claim 1 , wherein

A 2 is N;

B 1 is C—CF 3 ;

B 5 is C—Cl;

Q is cyclopropyl;

R 1 is H;

R 2 is H;

R 4 is Cl;

R 5 is H;

R 7 is H;

R 8 is i-C 3 F 7 ;

R 9 is H; and

R 11 is H.

13. The compound according to claim 1 , wherein

A 2 is N;

B 1 is C—CF 3 ;

B 5 is C—Cl;

Q is 1-cyano-cyclopropyl;

R 1 is H;

R 2 is H;

R 4 is Cl;

R 5 is H;

R 7 is H;

R 8 is i-C 3 F 7 ;

R 9 is H; and

R 11 is H.

14. The compound according to claim 1 , wherein

A 2 is C—H;

B 1 is C—OCF 3 ;

B 5 is C—Cl;

Q is cyclopropyl;

R 1 is H;

R 2 is H;

R 4 is Cl;

R 5 is H;

R 7 is H;

R 8 is i-C 3 F 7 ;

R 9 is H; and

R 11 is H.

15. The compound according to claim 1 , wherein R 4 is chlorine; R 6 is chlorine, methyl, trifluoromethyl, or trifluoromethoxy; R 8 is (CF 3 ) 2 CF—; and R 10 is chlorine or methyl.

16. The compound according to claim 1 having the formula (Ie)

wherein

(a) A 2 is C—H; B 1 is C—Cl; B 5 is C—Cl; Q is cyclopropyl; R 1 is H; R 2 is H; R 4 is Cl; R 5 is H; R 7 is H; R 8 is i-C 3 F 7 ; R 9 is H; and R 11 is H;

(b) A 2 is C—H; B 1 is C—Cl; B 5 is C—Cl; Q is 1-cyano-cyclopropyl; R 1 is H; R 2 is H; R 4 is Cl; R 5 is H; R 7 is H; R 8 is i-C 3 F 7 ; R 9 is H; and R 11 is H;

(c) A 2 is C—H; B 1 is C—CH 3 ; B 5 is C—CH 3 ; Q is cyclopropyl; R 1 is H; R 2 is H; R 4 is Cl; R 5 is H; R 7 is H; R 8 is i-C 3 F 7 ; R 9 is H; and R 11 is H;

(d) A 2 is C—H; B 1 is C—CH 3 ; B 5 is C—CH 3 ; Q is 1-cyano-cyclopropyl; R 1 is H; R 2 is H; R 4 is Cl; R 5 is H; R 7 is H; R 8 is i-C 3 F 7 ; R 9 is H; and R 11 is H;

(e) A 2 is N; B 1 is C—CH 3 ; B 5 is C—CH 3 ; Q is cyclopropyl; R 1 is H; R 2 is H; R 4 is Cl; R 5 is H; R 7 is H; R 8 is i-C 3 F 7 ; R 9 is H; and R 11 is H;

(f) A 2 is N; B 1 is C—CH 3 ; B 5 is C—CH 3 ; Q is 1-cyano-cyclopropyl; R 1 is H; R 2 is H; R 4 is Cl; R 5 is H; R 7 is H; R 8 is i-C 3 F 7 ; R 9 is H; and R 11 is H;

(g) A 2 is N; B 1 is C—CF 3 ; B 5 is C—CH 3 ; Q is cyclopropyl; R 1 is H; R 2 is H; R 4 is Cl; R 5 is H; R 7 is H; R 8 is i-C 3 F 7 ; R 9 is H; and R 11 is H;

(h) A 2 is N; B 1 is C—CF 3 ; B 5 is C—CH 3 ; Q is 1-cyano-cyclopropyl; R 1 is H; R 2 is H; R 4 is Cl; R 5 is H; R 7 is H; R 8 is i-C 3 F 7 ; R 9 is H; and R 11 is H;

(i) A 2 is N; B 1 is C—CF 3 ; B 5 is C—CH 3 ; Q is cyclopropyl; R 1 is CH 3 ; R 2 is H; R 4 is Cl; R 5 is H; R 7 is H; R 8 is i-C 3 F 7 ; R 9 is H; and R 11 is H;

(j) A 2 is N; B 1 is C—CF 3 ; B 5 is C—Cl; Q is cyclopropyl; R 1 is H; R 2 is H; R 4 is Cl; R 5 is H; R 7 is H; R 8 is i-C 3 F 7 ; R 9 is H; and R 11 is H;

(k) A 2 is N; B 1 is C—CF 3 ; B 5 is C—Cl; Q is 1-cyano-cyclopropyl; R 1 is H; R 2 is H; R 4 is Cl; R 5 is H; R 7 is H; R 8 is i-C 3 F 7 ; R 9 is H; and R 11 is H; or

(l) A 2 is C—H; B 1 is C—OCF 3 ; B 5 is C—Cl; Q is cyclopropyl; R 1 is H; R 2 is H; R 4 is Cl; R 5 is H; R 7 is H; R 8 is i-C 3 F 7 ; R 9 is H; and R 11 is H.

17. An insecticidal composition comprising a content of at least one compound according to claim 1 and an extender and/or a surface-active substance.

18. Seed in which a compound according to claim 1 is applied to seed as a constituent of a coating and/or as a further layer or further layers in addition to a coating.

19. A method for protecting transgenic or conventional seed and a plant that arises therefrom from infestation by pests, comprising treating seed with at least one compound according to claim 1 .

20. A method for controlling one or more pests comprising applying a compound according to claim 1 or an insecticidal composition thereof to one or more pests or to a habitat thereof.

21. A method of treating an animal comprising administering a compound according to claim 1 or an insecticidal composition thereof to the animal.

Assignments (3)
CHANGE OF NAME Recorded Feb 8, 2024
From: BAYER ANIMAL HEALTH GMBH
To: ELANCO ANIMAL HEALTH GMBH
Reel/Frame 066525/0898 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 23, 2016
From: BAYER CROPSCIENCE AKTIENGESELLSCHAFT
To: BAYER ANIMAL HEALTH GMBH
Reel/Frame 039846/0801 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 12, 2016
From: HALLENBACH, WERNER; GOERGENS, ULRICH; TURBERG, ANDREAS; ILG, KERSTIN; HORSTMANN, SEBASTIAN; KOEBBERLING, JOHANNES
To: BAYER CROPSCIENCE AKTIENGESSELLSCHAFT
Reel/Frame 039132/0270 →