Heterocyclic compounds as pesticides
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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.
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Citations
10 Claims
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1. A compound of formula (I)
- View Dependent Claims (2, 3, 4, 5, 6, 9, 10)
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2. 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 attacked 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 for their part are optionally substituted by alkyl, haloalkyl, alkoxy, or alkoxyalkyl).
- CH2, —
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3. 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).
- CH2, —
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4. The compound according to claim 1,
in which G1 represents CH or C-halogen; -
represents hydrogen or C1-C6-alkyl; and G2 represents A-R2a, D-R3b or E-R4c, 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, 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, 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, 1,2,5-thiadiazolyl, pyridyl, pyrimidinyl, pyridazinyl, azinyl, 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), 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 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 halogen, cyano, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, dioxolanyl or dihydrodioxazinyl, and c represents 1, 2 or 3.
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5. The compound according to claim 1,
in which G1 represents CH or C-halogen; -
R1 represents hydrogen; and G2 represents A-R2a, D-R3b or E-R4c, wherein A represents oxazolin-2-yl, 5,6-d hydro-[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, C1-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-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-2-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 of 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), 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, C1-C4-haloalkoxy, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio, C1-C4-alkylthio-C1-C4-alkyl or C3-C6-cycloalkyl), or 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 halogen, cyano, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy, c represents 1 or 2.
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6. The compound according to, claim 1,
in which G1 represents CH or C-halogen; -
R1 represents hydrogen; and G2 represents A-R2a or D-R3b, 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), 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-C5-cycloalkyl), or 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.
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9. A composition comprising, at least one compound according to claim 1 and one or more extenders, surfactants, or combinations thereof.
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10. A method for controlling pests comprising, contacting the compound according to claim 1 with said pests, their habitat, or a combination thereof.
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2. The compound according to claim 1,
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7. A compound of formula:
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8. A compound of formula:
Specification
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Current AssigneeBayer Intellectual Property GmbH (Bayer AG)
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Original AssigneeBayer Cropscience AG (Bayer AG)
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InventorsBretschneider, Thomas, Flein, Martin, Khler, Adeline, Mhlthau, Friedrich August, Franken, Eva-Maria, Voerste, Arnd
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Primary Examiner(s)RAO, DEEPAK R
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Application NumberUS12/902,878Publication NumberTime in Patent Office1,267 DaysField of Search544/65, 544/66, 544/124, 544/182, 544/296, 544/333, 546/256, 546/275.4, 514/229.2, 514/236.5, 514/242, 514/256, 514/333, 514/341US Class Current514/229.2CPC Class CodesA01N 43/54 1,3-Diazines; Hydrogenated ...A01N 43/56 1,2-Diazoles; Hydrogenated ...A01N 43/647 Triazoles; Hydrogenated tri...A01N 43/653 1,2,4-Triazoles; Hydrogenat...A01N 43/707 1,2,3- or 1,2,4-triazines; ...A01N 43/713 having rings with four or m...A01N 43/76 1,3-Oxazoles; Hydrogenated ...A01N 43/78 1,3-Thiazoles; Hydrogenated...A01N 43/82 five-membered rings with th...A01N 43/84 six-membered rings with one...A01N 43/88 six-membered rings with thr...A01N 55/08 containing boronC07D 213/84 NitrilesC07D 401/04 directly linked by a ring-m...C07D 403/04 directly linked by a ring-m...C07D 403/14 containing three or more he...C07D 405/14 containing three or more he...C07D 413/14 containing three or more he...C07D 417/14 containing three or more he...C07F 5/04 Esters of boric acids