Pyrazolyl derivatives as pest control agents

• US 10,202,351 B2
• Filed: 03/09/2016
• Issued: 02/12/2019
• Est. Priority Date: 03/10/2015
• Status: Active Grant

• Current Assignee: Bayer Vital GmbH (Bayer AG)
• Original Assignee: Bayer Vital GmbH (Bayer AG)
• Inventors: Schwarz, Hans-Georg, Maue, Michael, Hallenbach, Werner, Gorgens, Ulrich, Portz, Daniela, Ilg, Kerstin, Kobberling, Johannes, Turberg, Andreas
• Primary Examiner(s): Rodriguez-Garcia, Valerie
• Application Number:
  US15/554,501
• Publication Number:
  US 20180044298A1
• Time in Patent Office: 1,070 Days
• CPC Class Codes: A61P 33/00 Antiparasitic agents
• CPC Class Codes: C07D 231/12 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 401/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 401/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 401/14 containing three or more hetero rings
• CPC Class Codes: C07D 403/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 403/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 409/12 linked by a chain containing hetero atoms as chain links

Abstract

The invention comprises novel pyrazolyl derivatives of the general formula (I)

Also described are processes for preparing the compounds of the formula (I). The compounds according to the invention are especially suitable for controlling insects and archnids in agriculture, and ectoparasites in veterinary medicine.

Claims

1. A compound of formula (I)

2. The compound as claimed in claim 1, wherein B₁ is CR⁶, B₂ is CR⁷, B₃ is CR⁸, B₄ is CR⁹ and B₅ is CR¹⁰,

or a salt, N-oxide or a tautomeric form thereof.

3. The compound as claimed in claim 1, wherein R⁶ is halogen or optionally halogenated C₁-C₆-alkyl or optionally halogenated C₁-C₆-alkoxy, R⁷ is hydrogen, R⁸ is halogenated C₁-C₆-alkyl, R⁹ is hydrogen and R¹⁰ is halogen or optionally halogenated C₁-C₆-alkyl or optionally halogenated C₁-C₆-alkoxy,

or a salt, N-oxide or a tautomeric form thereof.

4. The compound as claimed in claim 1, wherein R¹¹ and R¹² are hydrogen and W is oxygen,

or a salt, N-oxide or a tautomeric form thereof.

5. The compound as claimed in claim 1, wherein A₁ is CR², A₂ is CR³ or N, A₃ is CR⁴ or N and A₄ is CR⁵ and R² is hydrogen or C₁-C₆-alkyl and R³, R⁴ and R⁵ are each independently of one another hydrogen, halogen, CN, optionally halogenated C₁-C₆-alkyl or optionally halogenated N,N-di-C₁-C₆-alkylamino,

or a salt, N-oxide or a tautomeric form thereof.

6. The compound as claimed in claim 1, wherein Q is

C₁-C₆-alkyl optionally substituted by one, two or three substituents selected from the group consisting of oxo, cyano, nitro and amino,

halogenated (C₁-C₆)-alkyl,

C₃-C₆-cycloalkyl optionally substituted by one, two or three substituents selected from the group consisting of halogen, cyano, nitro, C₁-C₃-alkyl and amino,

C₂-C₅-heterocyclyl optionally substituted with one, two or three substituents selected from the group consisting of halogen, cyano, nitro, C₁-C₃-alkyl and amino,

an aryl substituted by 0, 1, 2, 3 or 4 V substituents or

a 5- or 6-membered heteroaryl substituted by 0, 1, 2, 3 or 4 V substituents, wherein

V is independently of one another halogen, cyano, C₁-C₆-alkyl or C₁-C₆-alkoxy,

or a salt, N-oxide or a tautomeric form thereof.

7. The compound as claimed in claim 1, wherein Q is

C₃-C₆-cycloalkyl optionally substituted by one substituent selected from the group consisting of halogen, C₁-C₃-alkyl and cyano, or

C₂-C₅-heterocyclyl optionally substituted by one substituent selected from the group consisting of halogen or cyano, or

an aryl substituted by 0, 1 or 2 V substituents, or a 5- or 6-membered heteroaryl substituted by 0, 1, 2, 3 or 4 V substituents, wherein V is independently of one another halogen, cyano, C₁-C₆-alkyl or C₁-C₆-alkoxy,

or a salt, N-oxide or a tautomeric form thereof.

8. The compound as claimed in claim 1, wherein Q is

cyclopropyl optionally substituted by cyano or C₁-C₃-alkyl, or

thietanyl (thiacyclobutanyl) optionally substituted by cyano or C₁-C₃-alkyl, or

phenyl substituted by 0, 1 or 2 V substituents each selected independently of one another from the group consisting of F, Cl, C₁-C₃-alkoxy, C₁-C₃-alkyl, halogenated C₁-C₃-alkyl and cyano, or

pyridyl, pyrimidinyl, thienyl, or oxazolyl substituted by 0, 1 or 2 V substituents each selected independently of one another from the group consisting of F, Cl, C₁-C₃-alkyl, halogenated C₁-C₃-alkyl and cyano,

or a salt, N-oxide or a tautomeric form thereof.

9. The compound according to claim 1, where

A₁ represents CR², where R² represents hydrogen,

A₂ represents CR³ or N, where R³ represents hydrogen,

A₃ represents CR⁴ or N, where R⁴ is hydrogen, Cl, F, or C₁-C₃-alkyl or —

N(C₁-C₃-alkyl)₂,

A₄ represents CR⁵, where R⁵ represents hydrogen or F,

B₁ represents CR⁶,

B₂ represents CR⁷, where R⁷ represents hydrogen,

B₃ represents CR⁸,

B₄ represents CR⁹, where R⁹ represents hydrogen,

B₅ represents CR¹⁰

R⁶ represents Cl, Br or C₁-C₃-alkyl,

R⁸ represents perhalogenated C₁-C₆-alkyl,

R¹⁰ represents Cl, C₁-C₃-alkyl or perfluorinated C₁-C₃-alkyl,

R¹¹ and R¹² represent hydrogen,

W is oxygen,

Q represents (a) C₃-C₆-cycloalkyl optionally substituted by one substituent selected from the group consisting of halogen, C₁-C₃-alkyl and cyano, (b) C₂-C₅-heterocyclyl optionally substituted by one substituent selected from the group consisting of halogen, cyano, or C₁-C₃-alkyl, (c) an aryl substituted by 0, 1 or 2 V substituents or a 5- or 6-membered heteroaryl substituted by 0, 1, 2, 3 or 4 V substituents, wherein V is each independently of one another halogen, cyano, optionally halogenated C₁-C₆-alkyl, optionally halogenated C₁-C₆-alkoxy,

or a salt, N-oxide or a tautomeric form thereof.

10. The compound as claimed in claim 1, wherein the compound of the formula (I) is a compound of formula (I′

);

11. The compound as claimed in claim 1, wherein the compound of the formula (I) is a compound of formula (Ia):

12. The compound as claimed in claim 1, wherein the compound of the formula (I) is a compound of formula (Ib):

13. A pharmaceutical composition comprising a pharmaceutically acceptable auxiliary and at least one compound or salt, N-oxide or tautomeric form thereof as claimed in claim 1.

14. The compound or salt, N-oxide or tautomeric form thereof according to claim 1, wherein

R⁸ represents halogen, cyano, nitro or halogenated C₁-C₆-alkyl.

15. The compound according to claim 9, wherein

A₃ represents CR⁴ or N, where R⁴ is hydrogen, Cl, F, CH₃ or N(CH₃)₂,

R⁸ represents perfluorinated C₁-C₄-alkyl,

R¹⁰ represents Cl, methyl or CF₃,

Q represents (a) cyclopropyl optionally substituted by cyano or C₁-C₃-alkyl, (b) thietanyl (thiacyclobutanyl) optionally substituted by cyano or C₁-C₃-alkyl, (c) an aryl substituted by 0, 1 or 2 V substituents or a 5- or 6-membered heteroaryl substituted by 0, 1, 2, 3 or 4 V substituents, wherein V is each independently of one another F, Cl, cyano, optionally halogenated C₁-C₆-alkyl, optionally halogenated C₁-C₆-alkoxy,

or a salt, N-oxide or a tautomeric form thereof.

16. The compound according to claim 15, wherein

Q represents (a) cyclopropyl optionally substituted by cyano or C₁-C₃-alkyl, (b) thietanyl (thiacyclobutanyl) optionally substituted by cyano or C₁-C₃-alkyl, (c) phenyl optionally substituted by 0, 1 or 2 V substituents each selected independently of one another from the group consisting of F, Cl, methoxy, ethoxy, methyl, CF₃ and cyano;

or pyridyl, pyrimidinyl, thienyl, or oxazolyl optionally substituted by 0, 1 or 2 V substituents each selected independently of one another from the group consisting of F, Cl, methyl, CF₃ and cyano,

or a salt, N-oxide or a tautomeric form thereof.

17. The compound as claimed in claim 11, wherein

A₂ represents CH,

A₃ represents CH,

Q represents 4-F-phenyl,

R⁵ represents F,

R⁶ represents Br,

R⁸ represents iso-C₃F₇,

R¹⁰ represents CF₃,

or a salt, N-oxide or a tautomeric form thereof.