IP Library Granted Patent US 8,686,156
Granted Patent B2
US 8,686,156 · App. 13/099,977 · Granted Apr 1, 2014

Thiazole derivatives as pesticides

Inventors: Martin Füβlein (Düsseldorf, DE); Thomas Bretschneider (Lohmar, DE); Reiner Fischer (Monheim, DE); Peter Jeschke (Bergisch Gladbach, DE); Adeline Köhler (Wuppertal, DE); Joachim Kluth (Langenfeld, DE); Friedrich August Mühlthau (Bad Soden am Taunus, DE); Arnd Voerste (Köln, DE); Yoshitaka Sato (Ibaraki, JP)
Assignee: Bayer CropScience AG
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Quick Facts
Patent No.
US 8,686,156
App. No.
13/099,977
Granted
Apr 1, 2014
Kind
B2
Abstract

The present application relates to novel heterocyclic compounds, to their use for controlling animal pests including arthropods and in particular insects, and to processes for preparing the novel compounds.

Claims (37)

1. A compound of formula (I)

or a salt or N-oxide thereof,

in which

G 1 represents CH or C-halogen,

G 2 represents

in which

R 1 represents cyano, nitro, or halogen, and

G 3 represents a substituted heterocycle selected from the group consisting of dioxanyl, oxazolinyl, dihydrooxadiazinyl, dihydrodioxazinyl, and hydroxypyridyl; or heteroaryl which is substituted by an optionally substituted heterocyclyl selected from the group consisting of triazolinonyl, dihydrodioxazinyl, dihydrooxadiazinyl, dioxolanyl, dioxanyl, piperidinonyl, pyrrolidinonyl, and pyrazolinonyl; by an optionally substituted phenyl; by an optionally substituted heteroaryl; or by an optionally substituted heteroarylalkyl.

2. The compound according to claim 1 , in which G 3 represents a substituted heterocycle.

3. The compound according to claim 1 , in which G 3 represents substituted heteroaryl.

4. A method for controlling pests, comprising applying at least one compound according to claim 1 to a plant, a plant part, surroundings of a plant, environment of a plant, storage space of a plant, or a combination thereof.

5. A composition comprising at least one compound according to claim 1 and auxiliaries, solvents, carriers, surfactants, extenders, or combinations thereof.

6. The compound of claim 1 , wherein G 3 is 1,3-dioxan-2-yl.

7. The compound of claim 1 , wherein G 3 is 2-pyrimidinyl.

8. The compound of claim 1 , wherein R 1 is fluorine or chlorine.

9. The compound of claim 1 , wherein G 1 is CH.

10. The compound of claim 1 , wherein the compound is selected from the group consisting of:

2-[6-(4-Fluoro-2-pyridin-3-ylthiazol-5-yl)pyridin-2-yl]pyrimidine;

2-{6-[4-Chloro-2-(pyridin-3-yl)-1,3-thiazol-5-yl]pyridin-2-yl}pyrimidine; and

5 -Chloro-2-{6-[4-chloro-2-(pyridin-3-yl)-1,3-thiazol-5-yl]pyridin-2-yl}pyrimidine.

11. The compound of claim 1 , wherein G 3 is a heterocycle selected from the group consisting of 1,3-dioxan-2-yl, oxazolinyl, dihydrooxadiazinyl, dihydrodioxazinyl, and hydroxypyridyl, any of which is substituted by one or more halogen, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 -haloalkylsulphinyl, C 1 -C 6 -haloalkylsulphonyl, amino, C 1 -C 6 -alkylamino, di-(C 1 -C 6 -alkyl)amino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -alkoxycarbonylamino, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, aminocarbonyl, pyridyl, or pyrimidyl; or

is a heteroaryl selected from the group consisting of pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, benzofuryl, benzisofuryl, benzothienyl, benzisothienyl, indolyl, isoindolyl, indazolyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, benzimidazolyl, 2,1,3-benzoxadiazole, quinolinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, benzotriazinyl, purinyl, pteridinyl, and indolizinyl, any of which is substituted

by a heterocyclyl selected from the group consisting of triazolinonyl, dihydrodioxazinyl, dihydrooxadiazinyl, dioxolanyl, dioxanyl, piperidinonyl, pyrrolidinonyl, and pyrazolinonyl, any of which may be substituted by C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl;

by phenyl, which may be substituted by halogen, cyano, nitro, C 1 -C 6 -alkyl, or C 1 -C 6 -haloalkyl;

by a heteroaryl selected from the group consisting of pyrrolyl, pyridyl, pyridyl N-oxide, pyrimidyl, imidazolyl, pyrazolyl, oxazolyl, thiazolyl, furanyl, thienyl, triazolyl, oxadiazolyl, thiadiazolyl, pyrazinyl, triazinyl, tetrazinyl, and isoquinolinyl, any of which may be substituted by halogen, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 alkyl, C 1 -C 6 alkylthio-C 1 -C 6 -alkyl, or C 3 -C 6 -cycloalkyl; or

by a heteroarylalkyl selected from the group consisting of triazolyl-C 1 -C 6 -alkyl, pyridyl-C 1 -C 6 -alkyl, pyrimidyl-C 1 -C 6 -alkyl, and oxadiazolyl-C 1 -C 6 -alkyl, any of which may be substituted by C 1 -C 6 -alkyl.

12. The compound of claim 1 , wherein G 3 is a heterocycle selected from the group consisting of 1,3-dioxan-2-yl, oxazolinyl, dihydrooxadiazinyl, dihydrodioxazinyl and hydroxypyridyl, any of which is substituted by one or more halogen, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 -haloalkylsulphinyl, C 1 -C 6 -haloalkylsulphonyl, amino, C 1 -C 6 -alkylamino, di-(C 1 -C 6 alkyl)amino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -alkoxycarbonylamino, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 6-alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, aminocarbonyl, pyridyl, or pyrimidyl; or

is a heteroaryl selected from the group consisting of pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, benzofuryl, benzisofuryl, benzothienyl, benzisothienyl, indolyl, isoindolyl, indazolyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, benzimidazolyl, 2,1,3-benzoxadiazole, quinolinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, benzotriazinyl, purinyl, pteridinyl, and indolizinyl, any of which is substituted by a heterocyclyl selected from the group consisting of triazolinonyl, dihydrodioxazinyl, dihydrooxadiazinyl, dioxolanyl, dioxanyl, piperidinonyl, pyrrolidinonyl, and pyrazolinonyl;

by phenyl, which may be substituted by halogen, cyano, nitro, C 1 -C 6 -alkyl, or C 1 -C 6 -haloalkyl;

by a heteroaryl selected from the group consisting of pyrrolyl, pyridyl, pyridyl N-oxide, pyrimidyl, imidazolyl, pyrazolyl, oxazolyl, thiazolyl, furanyl, thienyl, triazolyl, oxadiazolyl, thiadiazolyl, pyrazinyl, triazinyl, tetrazinyl, and isoquinolinyl, any of which may be substituted by halogen, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylthio-C 1 -C 6 -alkyl, or C 3 -C 6 -cycloalkyl; or

by a heteroarylalkyl selected from the group consisting of triazolyl-C 1 -C 6 -alkyl, pyridyl-C 1 -C 6 -alkyl, pyrimidyl-C 1 -C 6 -alkyl, and oxadiazolyl-C 1 -C 6 -alkyl, any of which may be substituted by C 1 -C 6 -alkyl.

13. The compound of claim 1 , wherein G 3 is selected from the group consisting of optionally pyridyl- or pyrimidinyl-substituted 1,3-dioxan-2-yl, oxazolinyl, dihydrooxadiazinyl, and hydroxypyridyl; or

is selected from the group consisting of pyrazolyl, 1,2,4-oxadiazolyl, pyridyl, pyrimidinyl, 1,3,5-triazinyl, triazinyl, and oxadiazolyl, any of which is substituted

by a heterocyclyl selected from the group consisting of triazolinonyl, dihydrodioxazinyl, dihydrooxadiazinyl, piperidinonyl, pyrrolidinonyl, and pyrazolinonyl, any of which may be substituted by C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl;

by phenyl, which may be substituted by halogen;

by a heteroaryl selected from the group consisting of pyrrolyl, pyridyl, pyridyl N-oxide, pyrimidinyt, pyrazolyl, thiazolyl, furanyl, thienyl, triazolyl, oxadiazolyl, thiadiazelyl, pyrazinyl, triazinyl, and isoquinolinyi, any of which may be substituted by halogen, nitro, C 1 -C 4 -alkyl, C 1 C 1 haloalkyl, C 1 -C 4 -alkoxy, or C 3 -C 6 -cycloatkyl; or

by a heteroarylalkyl selected from the group consisting of triazolyl-C 1 -C 4 -alkyl, pyridyl-C 1 -C 4 -alkyl, pyrimidinyl-C 1 -C 4 -alkyl, and oxadiazolyl-C 1 -C 4 -alkyl, any of which may be substituted by C 1 -C 4 -alkyl.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 27, 2015
From: BAYER CROPSCIENCE AG
To: BAYER INTELLECTUAL PROPERTY GMBH
Reel/Frame 035051/0545 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 9, 2011
From: FUBLEIN, MARTIN; BRETSCHNEIDER, THOMAS; FISCHER, REINER; JESCHKE, PETER; KOHLER, ADELINE; KLUTH, JOACHIM; MUHLTHAU, FRIEDRICH AUGUST; VOERSTE, ARND; SATO, YOSHITAKA
To: BAYER CROPSCIENCE AG
Reel/Frame 026881/0914 →
Priority Claims (1)
EP 10162027 · May 5, 2010 · regional
Continuity (2)
Provisional Application 61332340 · May 7, 2010
Related Publication 20110319428A1 · Dec 29, 2011