Heterocyclic compounds as pesticides

• US 9,066,518 B2
• Filed: 02/04/2014
• Issued: 06/30/2015
• Est. Priority Date: 10/12/2009
• Status: Expired due to Fees

• Current Assignee: Bayer Intellectual Property GmbH (Bayer AG)
• Original Assignee: Bayer Intellectual Property GmbH (Bayer AG)
• Inventors: Bretschneider, Thomas, Flein, Martin, Khler, Adeline, Mhlthau, Friedrich August, Franken, Eva-Maria, Voerste, Arnd
• Primary Examiner(s): RAO, DEEPAK R
• Application Number:
  US14/172,332
• Publication Number:
  US 20140221362A1
• Time in Patent Office: 511 Days
• Field of Search: 544/296, 544/333, 514/256
• US Class Current: 1/1
• CPC Class Codes: A01N 43/54 1,3-Diazines; Hydrogenated 1,3-diazines
• CPC Class Codes: A01N 43/56 1,2-Diazoles; Hydrogenated 1,2-diazoles
• CPC Class Codes: A01N 43/647 Triazoles; Hydrogenated triazoles
• CPC Class Codes: A01N 43/653 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
• CPC Class Codes: A01N 43/707 1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
• CPC Class Codes: A01N 43/713 having rings with four or more nitrogen atoms as the only ring hetero atoms
• CPC Class Codes: A01N 43/76 1,3-Oxazoles; Hydrogenated 1,3-oxazoles
• CPC Class Codes: A01N 43/78 1,3-Thiazoles; Hydrogenated 1,3-thiazoles
• CPC Class Codes: A01N 43/82 five-membered rings with three ring hetero atoms
• CPC Class Codes: A01N 43/84 six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
• CPC Class Codes: A01N 43/88 six-membered rings with three ring hetero atoms
• CPC Class Codes: A01N 55/08 containing boron
• CPC Class Codes: C07D 213/84 Nitriles
• CPC Class Codes: C07D 401/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 403/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 403/14 containing three or more hetero rings
• CPC Class Codes: C07D 405/14 containing three or more hetero rings
• CPC Class Codes: C07D 413/14 containing three or more hetero rings
• CPC Class Codes: C07D 417/14 containing three or more hetero rings
• CPC Class Codes: C07F 5/04 Esters of boric acids

Abstract

The present application relates to the use of heterocyclic compounds, some of which are known, for controlling animal pests including arthropods and in particular insects, furthermore to novel heterocyclic compounds and to processes for their preparation.

Claims

1. A compound of formula (I), a salt, or an N-oxide thereof,

2. A composition comprising at least one compound of formula (I) according to claim 1, and one or more extenders, surfactants, or combinations thereof.

3. A method for controlling pests comprising contacting a compound of formula (I) according to claim 1 with the pests, their habitat, or a combination thereof.

4. The compound according to claim 1,

in which

R³ represents a heterocyclyl radical selected from the group consisting of dioxanyl, dioxolanyl, dioxepanyl, dioxocanyl, oxathianyl, oxathiolanyl, oxathiepanyl, oxathiocanyl, dithianyl, dithiolanyl, dithiepanyl, dithiocanyl, oxathianyl oxide, oxathiolanyl oxide, oxathiepanyl oxide, oxathiocanyl oxide, oxathianyl dioxide, oxathiolanyl dioxide, oxathiepanyl dioxide, oxathiocanyl dioxide (where in these heterocyclyl radicals two hydrogen atoms attached to the same carbon atom is optionally replaced by ═

CH₂, —

CH₂—

CH₂—

, —

CH₂—

CH₂—

CH₂—

or —

CH₂—

CH₂—

CH₂—

CH₂—

), morpholinyl, triazolinonyl, oxazolinyl, dihydrooxadiazinyl, dihydrodioxazinyl, dihydrooxazolyl, dihydrooxazinyl and pyrazolinonyl (where all the heterocyclyl radicals are optionally substituted by alkyl, haloalkyl, alkoxy, or alkoxyalkyl).

5. The compound according to claim 1,

in which

R⁴ represents a heterocyclyl radical selected from the group consisting of dioxanyl, dioxolanyl, dioxepanyl, dioxocanyl, oxathianyl, oxathiolanyl, oxathiepanyl, oxathiocanyl, dithianyl, dithiolanyl, dithiepanyl, dithiocanyl, oxathianyl oxide, oxathiolanyl oxide, oxathiepanyl oxide, oxathiocanyl oxide, oxathianyl dioxide, oxathiolanyl dioxide, oxathiepanyl dioxide, oxathiocanyl dioxide (where in these heterocyclyl radicals two hydrogen atoms attached to the same carbon atom is optionally replaced by ═

CH₂, —

CH₂—

CH₂—

, —

CH₂—

CH₂—

CH₂—

or —

CH₂—

CH₂—

CH₂—

CH₂—

), morpholinyl, triazolinonyl, oxazolinyl, dihydrooxadiazinyl, dihydrodioxazinyl, dihydrooxazolyl, dihydrooxazinyl and pyrazolinonyl (where all the heterocyclyl radicals are optionally substituted by alkyl, haloalkyl, alkoxy, or alkoxyalkyl).

6. The compound according to claim 1,

in which

R¹ represents hydrogen or C₁-C₆-alkyl;

and

G² represents A-R²_a, D-R³_b or E-R⁴_c,

wherein

A represents oxazolin-2-yl, 5,6-dihydro-[1,3,4]-oxadiazin-2-yl, 5,6-dihydro-[1,3,4]-thiadiazin-2-yl, 5,6-dihydro-[1,4,2]-dioxazin-3-yl or hydroxypyridyl,

R² represents a radical selected from the group consisting of halogen, cyano, nitro, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₆-haloalkylsulphinyl, C₁-C₆-haloalkylsulphonyl, amino, C₁-C₆-alkylamino, di-(C₁-C₆-alkyl)amino, C₁-C₆-alkylcarbonylamino, C₁-C₆-alkoxycarbonylamino, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-haloalkoxy-C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl-C₁-C₆-alkyl, C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl, aminocarbonyl, pyridyl and pyrimidyl (where pyridyl and pyrimidyl are optionally substituted by halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy),

a represents 0, 1, 2 or 3,

D represents a heteroaryl radical 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-benzoxadiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, benzotriazinyl, purinyl, pteridinyl and indolizinyl,

R³ represents a radical from the group consisting of C₃-C₆-cycloalkyl-C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl-C₁-C₆-alkyl, alpha-hydroxyimino-C₁-C₆-alkoxycarbonylmethyl and alpha-C₁-C₆-alkoxyimino-C₁-C₆-alkoxycarbonylmethyl, or

represents C(X)NR⁵R⁶ (in which X represents sulphur or NOH, R⁵ represents hydrogen or C₁-C₆-alkyl, and R⁶ represents a radical selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, cyano-C₁-C₆-alkyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl-C₁-C₆-alkyl, C₁-C₆-alkylthio-C₁-C₆-alkyl, phenyl-C₁-C₆-alkyl and hetaryl-C₁-C₆-alkyl in which hetaryl

represents pyrimidyl, or X represents sulphur, NOH or oxygen and R⁵ and R⁶ together with the nitrogen atom to which they are attached form a 5- to 7-membered ring which optionally contains one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulphur), or

represents NR⁷R⁸ (in which R⁷ represents hydrogen or C₁-C₆-alkyl and R⁸ represents a radical selected from the group consisting of C₂-C₆-alkynyl, C₃-C₆-cycloalkyl-C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkoxycarbonyl-C₁-C₆-alkyl, C₁-C₆-alkylthio-C₁-C₆-alkyl, phenyl-C₁-C₆-alkyl and hetaryl-C₁-C₆-alkyl in which hetaryl represents pyrimidyl, or R⁷ and R⁸ together with the nitrogen atom to which they are attached form a 5- to 7-membered ring which optionally contains one heteroatom selected from the group consisting of nitrogen, oxygen and sulphur), or

represents a heterocyclyl radical selected from the group consisting of dioxanyl, dioxolanyl, morpholinyl, triazolinonyl, oxazolinyl, dihydrooxadiazinyl, dihydrodioxazinyl and pyrazolinonyl (each of which is optionally substituted by C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy or C₁-C₆-alkoxy-C₁-C₆-alkyl), or

represents phenyl (which is substituted by halogen, cyano, nitro, C₁-C₆-alkyl or C₁-C₆-haloalkyl), or

represents a heteroaryl radical selected from the group consisting of pyridyl, pyridyl N-oxide, pyrimidyl, imidazolyl, pyrazolyl, oxazolyl, thiazolyl, furanyl, thienyl, triazolyl, oxadiazolyl, thiadiazolyl, pyrazinyl, triazinyl, tetrazinyl and isoquinolinyl (each of which is optionally substituted by halogen, nitro, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkylthio, C₁-C₆-alkylthio-C₁-C₆-alkyl or C₃-C₆-cycloalkyl), or

represents a heteroarylalkyl radical selected from the group consisting of triazolyl-C₁-C₆-alkyl, pyridyl-C₁-C₆-alkyl, pyrimidyl-C₁-C₆-alkyl and oxadiazolyl-C₁-C₆-alkyl (each of which is optionally substituted by C₁-C₆-alkyl),

b represents 0, 1, 2 or 3,

E represents phenyl,

R⁴ represents cyano, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, dioxolanyl or dihydrodioxazinyl,

and

c represents 1, 2 or 3.

7. The compound according to claim 1,

in which

R¹ represents hydrogen;

and

G² represents A-R²_a, D-R³_b or E-R⁴_c,

wherein

A represents oxazolin-2-yl, 5,6-dihydro-[1,3,4]-oxadiazin-2-yl 5,6-dihydro-[1,3,4]-thiadiazin-2-yl or 5,6-dihydro-[1,4,2]-dioxazin-3-yl,

R² represents a radical selected from the group consisting of halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl, C₁-C₄-haloalkylsulphinyl, C₁-C₄-haloalkylsulphonyl, amino, C₁-C₄-alkylamino, di-(C₁-C₄-alkyl)amino, C₁-C₄-alkylcarbonylamino, C₁-C₄-alkoxycarbonylamino, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, aminocarbonyl, pyridyl and pyrimidyl (where pyridyl and pyrimidyl are optionally substituted by halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy),

a represents 0, 1, 2 or 3,

D represents a heteroaryl radical selected from the group consisting of pyrid-2-yl, pyrid-3-yl, pyrimid-2-yl, pyrimid-4-yl, imidazolyl, pyrazol-1-yl, pyrazol-3-yl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, thiazol-2-yl, thiazol-4-yl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl and oxazolyl,

R³ represents a radical selected from the group consisting of C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl, alpha-hydroxyimino-C₁-C₄-alkoxycarbonylmethyl and alpha-C₁-C₄-alkoxyimino-C₁-C₄-alkoxycarbonylmethyl, or

represents C(X)NR⁵R⁶ (in which X represents sulphur, R⁵ represents hydrogen or C₁-C₄-alkyl and R⁶ represents a radical selected from the group consisting of hydrogen, C₁-C₅-alkyl, C₁-C₄-haloalkyl, cyano-C₁-C₄-alkyl, C₂-C₄-alkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl and phenyl-C₁-C₄-alkyl, or X represents sulphur or oxygen and R⁵ and R⁶ together with the nitrogen atom to which they are attached form a 5- to 7-membered ring which optionally contains one heteroatom selected from the group consisting of nitrogen, oxygen and sulphur), or

represents NR⁷R⁸ (in which R⁷ represents hydrogen or C₁-C₄-alkyl and R⁸ represents a radical selected from the group consisting of C₂-C₄-alkynyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl and phenyl-C₁-C₄-alkyl, or R⁷ and R⁸ together with the nitrogen atom to which they are attached form a 5- or 6-membered ring which optionally contains one heteroatom selected from the group consisting of oxygen, sulphur and nitrogen), or

represents a heterocyclyl radical selected from the group consisting of dioxanyl, dioxolanyl, morpholinyl, triazolinonyl, oxazolinyl, dihydrooxadiazinyl, dihydrodioxazinyl and pyrazolinonyl (each of which is optionally substituted by C₁-C₄-alkyl or C₁-C₄-haloalkyl), or

represents phenyl (which is optionally substituted by halogen, cyano, nitro, C₁-C₄-alkyl or C₁-C₄-haloalkyl), or

represents a heteroaryl radical selected from the group consisting of pyridyl, pyridyl N-oxide, pyrimidyl, imidazolyl, pyrazolyl, oxazolyl, thiazolyl, furanyl, thienyl, triazolyl, oxadiazolyl, thiadiazolyl, pyrazinyl, triazinyl, tetrazinyl and isoquinolinyl (each of which is optionally substituted by halogen, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, haloalkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl or C₃-C₆-cycloalkyl), or

represents a heteroarylalkyl radical selected from the group consisting of triazolyl-C₁-C₄-alkyl, pyridyl-C₁-C₄-alkyl, pyrimidyl-C₁-C₄-alkyl and oxadiazolyl-C₁-C₄-alkyl (each of which is optionally substituted by C₁-C₄-alkyl),

b represents 0, 1 and 2,

E represents phenyl,

R⁴ represents cyano, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy,

and

c represents 1 or 2.

8. The compound according to claim 1,

in which

R¹ represents hydrogen;

and

G² represents A-R²_a or D-R³_b,

wherein

A represents oxazolin-2-yl, 5,6-dihydro-[1,3,4]-oxadiazin-2-yl, or 5,6-dihydro-[1,3,4]-thiadiazin-2-yl,

R² represents pyridyl and pyrimidyl which are optionally substituted by halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy,

a represents 0, 1 or 2,

D represents pyrazol-1-yl, pyrazol-3-yl, pyrid-3-yl, pyrid-2-yl, pyramid-2-yl pyramid-4-yl, thiazol-2-yl or thiazol-4-yl,

R³ represents a radical selected from the group consisting of C₃-C₆-cycloalkyl-C₁-C₄-alkyl and alpha-hydroxyimino-C₁-C₄-alkoxycarbonylmethyl, or

represents C(X)NR⁵R⁶ (in which X represents sulphur, R⁵ represents hydrogen and R⁶ represents a radical selected from the group consisting of hydrogen, C₁-C₅-alkyl, C₁-C₄-haloalkyl, cyano-C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl and phenyl-C₁-C₄-alkyl, or X represents sulphur or oxygen and R⁵ and R⁶ together with the nitrogen atom to which they are attached form a 5- to 7-membered ring which optionally contains a heteroatom selected from the group consisting of nitrogen, oxygen and sulphur), or

represents NR⁷R⁸ (in which R⁷ represents hydrogen or methyl and R⁸ represents C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl, or R⁷ and R⁸ together with the nitrogen atom to which they are attached form a 5- or 6-membered ring which optionally contains an oxygen atom, or

represents a heterocyclyl radical selected from the group consisting of dioxanyl, dioxolanyl, morpholinyl, triazolinonyl, oxazolinyl, dihydrooxadiazinyl, dihydrodioxazinyl and pyrazolinonyl (each of which is optionally substituted by C₁-C₄-alkyl or C₁-C₄-haloalkyl), or

represents phenyl (which is optionally substituted by halogen), or

represents a heteroaryl radical selected from the group consisting of pyridyl, pyridyl N-oxide, pyrimidinyl, pyrazolyl, thiazolyl, furanyl, thienyl, triazolyl, oxadiazolyl, thiadiazolyl, pyrazinyl, triazinyl, and isoquinolinyl (each of which is optionally substituted by halogen, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, or C₃-C₆-cycloalkyl), or

represents a heteroarylalkyl radical selected from the group consisting of triazolyl-C₁-C₄-alkyl, pyridyl-C₁-C₄-alkyl, pyrimidinyl-C₁-C₄-alkyl and oxadiazolyl-C₁-C₄-alkyl (each of which is optionally substituted by C₁-C₄-alkyl),

and

b represents 0, 1 or 2.

9. A compound of formula (I), a salt, or an N-oxide thereof,

10. The compound according to claim 9,

in which

R⁴ represents a heterocyclyl radical selected from the group consisting of dioxanyl, dioxolanyl, dioxepanyl, dioxocanyl, oxathianyl, oxathiolanyl, oxathiepanyl, oxathiocanyl, dithianyl, dithiolanyl, dithiepanyl, dithiocanyl, oxathianyl oxide, oxathiolanyl oxide, oxathiepanyl oxide, oxathiocanyl oxide, oxathianyl dioxide, oxathiolanyl dioxide, oxathiepanyl dioxide, oxathiocanyl dioxide (where in these heterocyclyl radicals two hydrogen atoms attached to the same carbon atom is optionally replaced by ═

CH₂, —

CH₂—

CH₂—

, —

CH₂—

CH₂—

CH₂—

or —

CH₂—

CH₂—

CH₂—

CH₂—

), morpholinyl, triazolinonyl, oxazolinyl, dihydrooxadiazinyl, dihydrodioxazinyl, dihydrooxazolyl, dihydrooxazinyl and pyrazolinonyl (where all the heterocyclyl radicals are optionally substituted by alkyl, haloalkyl, alkoxy, or alkoxyalkyl).

11. The compound according to claim 9,

in which

E represents phenyl,

R⁴ represents halogen, cyano, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, dioxolanyl or dihydrodioxazinyl,

and

c represents 1, 2 or 3.

12. The compound according to claim 9,

in which

E represents phenyl,

R⁴ represents halogen, cyano, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy,

and

c represents 1 or 2.

13. A composition comprising at least one compound of formula (I) according to claim 9, and one or more extenders, surfactants, or combinations thereof.

14. A method for controlling pests comprising contacting a compound of formula (I) according to claim 9 with the pests, their habitat, or a combination thereof.