IP Library Granted Patent US 10,273,226
Granted Patent B2
US 10,273,226 · App. 15/109,630 · Granted Apr 30, 2019

Pyrazolyl-heteroarylamides as pesticides

Inventors: Hans-Georg Schwarz (Dorsten, DE); Michael Maue (Langenfeld, DE); Kerstin Ilg (Köln, DE); Ulrich Görgens (Ratingen, DE); Andreas Turberg (Haan, DE); Sebastian Horstmann (Leverkusen, DE); Johannes Köbberling (Neuss, DE); Niels Lindner (Wuppertal, DE)
Assignee: BAYER ANIMAL HEALTH GMBH
C07D403/04A01N43/56A01N43/76A01N43/90C07D231/38C07D401/14C07D403/14C07D407/14C07D409/14C07D413/14C07D487/04
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Quick Facts
Patent No.
US 10,273,226
App. No.
15/109,630
Granted
Apr 30, 2019
Kind
B2
Abstract

The invention comprises, inter alia, pyrazolylheteroarylamides of the general formula (I) in which the A 1 -A 4 , T, W, Q, R 1 and Z 1 -Z 3 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 (31)

1. A compound of the formula (Ic)

in which

R 1 is hydrogen or CH 3 ;

Z 1 is CF 2 CF 3 ;

Z 2 is CF 3 ;

Z 3 is CH 3 ,

A 1 is CH;

A 2 is CH or nitrogen;

A 3 is CR 4 ;

R 4 is fluorine; chlorine; hydrogen; or CH 3 ;

A 4 is CR 5 ,

R 5 is fluorine or hydrogen;

n is 0;

W is oxygen; and

Q is ethyl; isopropyl; t-butyl; cyclopentyl; phenoxyethyl; benzyloxymethyl; CF 3 CH 2 —; CHF 2 CF 2 —; MeOCH 2 —; MeOCH 2 CH 2 —; 3-pyridinyl; 4-pyridinyl; 2-F-4-pyridinyl; 3-F-4-pyridinyl; 3-F-5-pyridinyl; 3-Cl-2-pyridinyl; 2-Cl-3-pyridinyl; 2-Cl-4-pyridinyl; 2-Cl-5-pyridinyl; 2,6-Cl 2 -4-pyridinyl; 2-Cl-6-Me-4-pyridinyl; 2-Me-4-pyridinyl; 2-CN-5-pyridinyl; 2-F-5-pyridinyl; phenyl; 2-F-phenyl; 3-F-phenyl; 4-F-phenyl; 3,5-F 2 -phenyl; 2,6-F 2 -phenyl; 3-MeO-phenyl; 2,3-F 2 -phenyl; 2-EtO-phenyl; 2-CF 3 O-phenyl; 3-cyanophenyl; 4-CN-phenyl; phenylthiomethyl; 2-thiophenyl; 3-thiophenyl; 3-Cl-2-thiophenyl; 2-thiophenyl-methyl; 3-Cl-benzothiophen-2-yl; 3-Cl-6-Me-benzothiophen-2-yl; cyclopropyl; 1-CN-cyclopropyl; 1-Cl-cyclopropyl; 1-Me-cyclopropyl; 1-phenylcycloprop-1-yl; 1-oxazolyl; 5-methylisoxazol-4-yl; 2-pyrimidinyl; 4-pyrimidinyl; 7-(difluoromethyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl; 1-methyl-4-pyrazolyl; 1-Me-3-tBu-4-NO 2-5 -pyrazolyl; 3-CF 3 -4-Me-pyrazol-1-yl-methyl; (1,1-dimethyl)-2-fluoroethyl; cis/trans-4-MeO-cyclohex-1-yl; 1-Me-cyclohex-1-yl; 3-CF 3 -4-F-phenyl; 3-CF 3 -phenyl; 4-Me-phenyl; 2,6-(MeO) 2 -phenyl; 4-(Me 2 N)-phenyl; 2,4,6-(iPr) 3 -phenyl; 3-Me-2-benzofuranyl; 2-CF 3 -4-Me-furan-2-yl; 1,1,2,2-tetramethylethyl; (R)-1-F-ethyl; 2-Me-3-furanyl; 2-Me-prop-1-yl; 5-Me-thien-2-yl; 2,2-dimethylprop-1-yl; 2,3-dimethylphenyl; 1,1-dimethyl-2-ethoxyethyl; 2,2-difluoro-1,3-benzodioxol-5-yl; 3,4-dimethylphenyl; 3-Me, 4-F-phenyl; 3-F, 4-Me-phenyl; 3-F, 4-MeO-phenyl; 1,3-benzodioxol-5-yl; 4-Cl, 3-F-phenyl; 3-MeO, 4-Me-Ph; 3-EtO, 4-F-phenyl; 3-EtO-4-F-phenyl; 3-MeO-4-F-phenyl; 3-F-4-MeO-phenyl; 1-(4-Me-phenyl)cyclohex-1-yl; 3-CF 3 -benzyl; 3-F-benzyl; 2-Cl-4-F-benzyl; 1-methyl-1-(3-Cl-phenyl)ethyl; 1-(4-Cl-phenyl)-cyclobut-1-yl; (rac)-1-phenylethyl; (rac)-phenyl-cyclopentylmethyl; (rac)-tetralin; (rac)-1-(4-Cl-phenyl)-2-methyl-prop-1-yl; (rac)-1-phenoxy-ethyl; (rac)-1-phenyl-prop-1-yl; (rac)-1-methylpropyl; 2-phenylethyl; N′,N′-dimethyloxalyl-amide; 3-MeO, 4-F-phenyl; 3-F; or 4-MeO-phenyl.

2. The compound according to claim 1 , in which R 1 is hydrogen.

3. The compound according to claim 1 , in which R 1 is CH 3 .

4. The compound according to claim 1 , in which the compound is of the formula (Ic-1)

5. The compound according to claim 1 , in which the compound is of the formula (Ic-2)

6. A method for control of at least one of insects, arachnids, and nematodes comprising administering an effective amount of the compound according to claim 1 of the formula (Ic).

7. A pharmaceutical composition comprising at least one compound comprising to claim 1 in combination with a pharmaceutically acceptable excipient and/or an auxiliary.

8. A medicament comprising the compound according to claim 1 in combination with a pharmaceutically acceptable excipient and/or an auxiliary.

9. A method of making a crop protection composition comprising combining the compound according to claim 1 with an extender and/or a surfactant.

10. A method for controlling pests, comprising administering an effective amount of the compound according to claim 1 to plants, seeds, crops, animals, pests and/or the pest's habitat.

11. A method for protection of propagation material of plants comprising administering an effective amount of the compound according to claim 1 to the plants or their propagation material.

12. The compound according to claim 1 , in which R 4 is fluorine.

13. The compound according to claim 1 , in which R 4 is chlorine.

14. The compound according to claim 1 , in which R 4 is hydrogen.

15. The compound according to claim 1 , in which R 4 is CH 3 .

16. The compound according to claim 1 , in which R 5 is hydrogen.

17. The compound according to claim 1 , in which R 5 is fluorine.

Assignments (2)
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 Jul 18, 2016
From: SCHWARZ, HANS-GEORG, DR.; MAUE, MICHAEL, DR.; ILG, KERSTIN, DR.; GÖRGENS, ULRICH; TURBERG, ANDREAS, DR.; HORSTMANN, SEBASTIAN, DR.; KÖBBERLING, JOHANNES, DR.; LINDNER, NIELS
To: BAYER ANIMAL HEALTH GMBH
Reel/Frame 039177/0134 →
Priority Claims (1)
EP 14150153 · Jan 3, 2014 · regional
Continuity (1)
Related Publication 20160326140A1 · Nov 10, 2016