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US 9,066,518 B2Granted
Heterocyclic compounds as pesticides
AssigneeBayer Intellectual Property GmbH
InventorsThomas Bretschneider, Martin Füβlein, Adeline Köhler, Friedrich August Mühlthau, Eva-Maria Franken, Arnd Voerste
Life of this patent
Estimating the term…
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.
Claims14
A compound of formula (I), a salt, or an N-oxide thereof,
- in which
- G1 represents N,
- R1 represents hydrogen, alkyl, haloalkyl, cycloalkyl, halogen, cyano, alkoxy, haloalkoxy, amino, alkylamino, dialkylamino or alkylthio,
- G2 represents A-R2a, D-R3b or E-R4c, in which
- A represents a heterocyclyl selected from the group consisting of 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, oxazolin-2-yl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 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, hydroxypyridyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1,3,5-hexahydrotriazin-2-yl and 1,2,4-hexahydrotriazin-3-yl,
- R2 represents a radical selected from the group consisting of halogen, cyano, nitro, alkyl, haloalkyl, optionally substituted cycloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulphinyl, alkylsulphonyl, haloalkylsulphinyl, haloalkylsulphonyl, amino, alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonylamino, alkoxyalkyl, haloalkoxyalkyl, alkenyl, alkynyl, optionally substituted cycloalkylalkyl, alkylcarbonyl, alkoxycarbonyl, aminocarbonyl, pyridyl and pyrimidyl (where pyridyl and pyrimidyl are optionally substituted by halogen, alkyl, haloalkyl, alkoxy and haloalkoxy),
- a represents a number selected from the group consisting of 0, 1, 2 and 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 selected from the group consisting of optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted cycloalkylalkyl (where in the cycloalkyl moiety of the cycloalkylalkyl radical one or two CH2 groups is optionally replaced by oxygen or sulphur, but two oxygen atoms must not be directly adjacent to one another), bis(alkoxy)alkyl, bis(haloalkoxy)alkyl, alkoxy(alkylsulphanyl)alkyl, alkoxy(alkylsulphinyl)alkyl, alkoxy(alkylsulphonyl)alkyl, bis(alkylsulphanyl)alkyl, bis(haloalkylsulphanyl)alkyl, bis(hydroxyalkylsulphanyl)alkyl, alkoxycarbonylalkyl, alpha-hydroxyimino-alkoxycarbonylalkyl, and alpha-alkoxyimino-alkoxycarbonylalkyl, or
- represents C(X)NR5R6 (in which X represents sulphur, or NOH, R5 represents hydrogen or alkyl, and R6 represents a radical selected from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkylcarbonyl, alkoxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, aryl, arylalkyl and hetarylalkyl, or X represents sulphur, NOH, NR15 or oxygen, R15 represents a radical selected from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkylcarbonyl, alkoxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, aryl, arylalkyl and hetarylalkyl, and R5 and R6 together with the nitrogen atom to which they are attached form a ring which optionally contains one or more further heteroatoms selected from the group consisting of NH, NCH3, NC2H5, oxygen and sulphur, where two oxygen atoms must not be directly adjacent to one another, or R5 and R15 together with the nitrogen atoms to which they are attached form a ring which optionally contain one or more further heteroatoms selected from the group consisting of NH, NCH3, NC2H5, oxygen and sulphur, where two oxygen atoms must not be directly adjacent to one another), or
- represents NR7R8 (in which R7 represents hydrogen or alkyl and R8 represents alkynyl, cycloalkylalkyl, alkoxy, haloalkoxy, alkoxycarbonylalkyl, alkylthioalkyl, arylalkyl or hetarylalkyl, or R7 and R8 together with the nitrogen atom to which they are attached form a ring which optionally contains one or more further heteroatoms selected from the group consisting of NH, NCH3, NC2H5, oxygen and sulphur, where two oxygen atoms must not be directly adjacent to one another), or
- 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 are optionally replaced by ═CH2, —CH2—CH2—, —CH2—CH2—CH2— or —CH2—CH2—CH2—CH2—), morpholinyl, triazolinonyl, oxazolinyl, dihydrooxadiazinyl, dihydrodioxazinyl, dihydrooxazolyl, dihydrooxazinyl and pyrazolinonyl, wherein said heterocyclyl radical is optionally substituted by alkyl, haloalkyl, alkoxy or alkoxyalkyl, or
- represents phenyl, wherein said phenyl is optionally substituted by halogen, cyano, nitro, alkyl or haloalkyl, or
- represents a heteroaryl radical selected from the group consisting of pyridyl, pyridyl N-oxide, pyrimidyl, imidazolyl, pyrazolyl, oxazolyl, thiazolyl, furanyl, thienyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyrazinyl, triazinyl, tetrazinyl and isoquinolinyl, wherein said heteroaryl radical is optionally substituted by halogen, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxyalkyl, alkylthio, alkylthioalkyl or cycloalkyl, or
- represents a heteroarylalkyl radical selected from the group consisting of triazolylalkyl, pyridylalkyl, pyrimidylalkyl and oxadiazolylalkyl, wherein said heteroarylalkyl radical is optionally substituted by alkyl,
- b represents a number selected from the group consisting of 1, 2 and 3,
- E represents aryl,
- R4 represents a radical selected from the group consisting of nitro, amino, formyl, cyano, alkylamino, haloalkylamino, dialkylamino, alkyl, haloalkyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted cycloalkylalkyl (where in the cycloalkyl moiety of the cycloalkylalkyl radical one or two CH2 groups is optionally replaced by oxygen or sulphur, but two oxygen atoms must not be directly adjacent to one another), alkoxy, haloalkoxy, alkoxyalkyl, halogenated alkoxyalkyl, bis(alkoxy)alkyl, bis(haloalkoxy)alkyl, alkoxy(alkylsulphanyl)alkyl, alkoxy(alkylsulphinyl)alkyl, alkoxy(alkylsulphonyl)alkyl, bis(alkylsulphanyl)alkyl, bis(haloalkylsulphanyl)alkyl, bis(hydroxyalkylsulphanyl)alkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alpha-hydroxyimino-alkoxycarbonylalkyl, and alpha-alkoxyimino-alkokycarbonylalkyl, or
- represents C(X)NR5R6 (in which X represents oxygen, sulphur, NR15 or NOH, R5 represents hydrogen or alkyl and R6 and R15 independently of one another represent a radical selected from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkylcarbonyl, alkoxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, aryl, arylalkyl and hetarylalkyl, or R6 represents OH, or R5 and R6 together with the nitrogen atom to which they are attached form a ring which optionally contain one or more further heteroatoms selected from the group consisting of NH, NCH3, NC2H5, oxygen and sulphur, where two oxygen atoms must not be directly adjacent to one another, or R5 and R15 together with the nitrogen atoms to which they are attached form a ring which optionally contain one or more further heteroatoms selected from the group consisting of NH, NCH3, NC2H5, oxygen and sulphur, where two oxygen atoms must not be directly adjacent to one another), or
- represents NR7R8 (in which R7 represents hydrogen or alkyl and R8 represents a radical selected from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, haloalkoxy, alkoxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, aryl, arylalkyl and hetarylalkyl, or R7 and R8 together with the nitrogen atom to which they are attached form a ring which optionally contain one or more further heteroatoms selected from the group consisting of NH, NCH3, NC2H5, oxygen and sulphur), or
- represents alkylthio, alkylsulphinyl, alkylsulphonyl, or
- 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 are 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 for their part are optionally substituted by alkyl, haloalkyl, alkoxy or alkoxyalkyl), or
- represents phenyl, wherein said phenyl is substituted by halogen, cyano, nitro, alkyl or haloalkyl, or
- represents a heteroaryl radial selected from the group consisting of pyridyl, pyridyl N-oxide, pyrimidyl, imidazolyl, pyrazolyl, oxazolyl, thiazolyl, furanyl, thienyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyrazinyl, triazinyl, tetrazinyl and isoquinolinyl, wherein said heteroaryl radial is optionally substituted by halogen, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxyalkyl, alkylthio, alkylthioalkyl or cycloalkyl, or
- represents a heteroarylalkyl radical selected from the group consisting of triazolylalkyl, pyridylalkyl, pyrimidylalkyl oxadiazolylalkyl, wherein said heteroarylalkyl radical is optionally substituted by halogen or alkyl, and
- c represents a number selected from the group consisting of 0, 1, 2 and 3.
23 more elements
A compound of formula (I), a salt, or an N-oxide thereof,
- in which
- G1 represents N,
- R1 represents alkyl, haloalkyl, cycloalkyl, halogen, cyano, alkoxy, haloalkoxy, amino, alkylamino, dialkylamino or alkylthio,
- G2 represents E-R4c, in which
- E represents aryl,
- R4 represents a radical selected from the group consisting of halogen, nitro, amino, formyl, cyano, alkylamino, haloalkylamino, dialkylamino, alkyl, haloalkyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted cycloalkylalkyl (where in the cycloalkyl moiety of the cycloalkylalkyl radical one or two CH2 groups is optionally replaced by oxygen or sulphur, but two oxygen atoms must not be directly adjacent to one another), alkoxy, haloalkoxy, alkoxyalkyl, halogenated alkoxyalkyl, bis(alkoxy)alkyl, bis(haloalkoxy)alkyl, alkoxy(alkylsulphanyl)alkyl, alkoxy(alkylsulphinyl)alkyl, alkoxy(alkylsulphonyl)alkyl, bis(alkylsulphanyl)alkyl, bis(haloalkylsulphanyl)alkyl, bis(hydroxyalkylsulphanyl)alkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alpha-hydroxyimino-alkoxycarbonylalkyl, and alpha-alkoxyimino-alkokycarbonylalkyl, or
- represents C(X)NR5R6 (in which X represents oxygen, sulphur, NR15 or NOH, R5 represents hydrogen or alkyl and R6 and R15 independently of one another represent a radical selected from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkylcarbonyl, alkoxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, aryl, arylalkyl and hetarylalkyl, or R6 represents OH, or R5 and R6 together with the nitrogen atom to which they are attached form a ring which optionally contain one or more further heteroatoms selected from the group consisting of NH, NCH3, NC2H5, oxygen and sulphur, where two oxygen atoms must not be directly adjacent to one another, or R5 and R15 together with the nitrogen atoms to which they are attached form a ring which optionally contain one or more further heteroatoms selected from the group consisting of NH, NCH3, NC2H5, oxygen and sulphur, where two oxygen atoms must not be directly adjacent to one another), or
- represents NR7R8 (in which R7 represents hydrogen or alkyl and R8 represents a radical selected from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, haloalkoxy, alkoxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, aryl, arylalkyl and hetarylalkyl, or R7 and R8 together with the nitrogen atom to which they are attached form a ring which optionally contain one or more further heteroatoms selected from the group consisting of NH, NCH3, NC2H5, oxygen and sulphur), or
- represents alkylthio, alkylsulphinyl, alkylsulphonyl, or
- 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 are 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 for their part are optionally substituted by alkyl, haloalkyl, alkoxy or alkoxyalkyl), or
- represents phenyl, wherein said phenyl is substituted by halogen, cyano, nitro, alkyl or haloalkyl, or
- represents a heteroaryl radial selected from the group consisting of pyridyl, pyridyl N-oxide, pyrimidyl, imidazolyl, pyrazolyl, oxazolyl, thiazolyl, furanyl, thienyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyrazinyl, triazinyl, tetrazinyl and isoquinolinyl, wherein said heteroaryl radial is optionally substituted by halogen, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxyalkyl, alkylthio, alkylthioalkyl or cycloalkyl, or
- represents a heteroarylalkyl radical selected from the group consisting of triazolylalkyl, pyridylalkyl, pyrimidylalkyl oxadiazolylalkyl, wherein said heteroarylalkyl radical is optionally substituted by halogen or alkyl,
- and
- c represents a number selected from the group consisting of 0, 1, 2 and 3.
12 more elements
Dependencies are inferred from the claim text.