Ortho-substituted 2-methoxyiminophenyl-N-methylacetamides
First Claim
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1. A compound of formula I whereinn is 0, 1, 2, 3 or 4, or, when R1 is nitro or cyano, n is 1 or 2, and wherein R1 can be the same or different if n is greater than 1;
- X is O or S;
Y is a five-membered heteroaromatic ring which has 1-3 nitrogens and 2-4 carbons or 1-2 nitrogens, 1 oxygen or 1 sulfur, and 2-3 carbons which can be substituted with one or two radicals selected from the group consisting of Cl, CH3, CF3 and OCH3;
R1 is nitro;
cyano;
halogen;
C1-C4-alkyl;
C1-C4-haloalkyl;
C1-C4-alkoxy;
C1-C4-haloalkoxy;
C1-C4-alkylthio;
phenyl or phenoxy, the aromatic rings may carry one to five halogen atoms or one to three of the following radicals selected from the group consisting of halogen, C1-C4-alkyl;
C1-C4-haloalkyl;
C1-C4-alkoxy;
C1-C4-haloalkoxy and C1-C4-alkylthio;
or, if n is greater than 1, a 1,3-butadiene-1,4-diyl group which is bonded to two adjacent C atoms of the phenyl radical and which may carry one to four halogen atoms or one or two of the following radicals selected from the group consisting of halogen, nitro, cyano, C1-C4-alkyl;
C1-C4-haloalkyl;
C1-C4-alkoxy;
C1-C4-haloalkoxy and C1-C4-alkylthio;
R2 is unsubstituted or substituted C1-C4 alkyl, unsubstituted or substituted C3-C6 cycloalkyl, or unsubstituted or substituted phenyl, cyano, acetyl or unsubstituted or substituted aromatic heterocycles containing one to three nitrogen and/or an oxygen or sulfur atom.
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Abstract
Compounds of the general formula I
where the index and the substituents have the following meanings:
n is 0 or 1 to 4;
X is O or S;
Y is a five-membered heteroaromatic ring;
R1 is nitro; cyano; halogen;
alkyl; haloalkyl; alkoxy; haloalkoxy; alkylthio;
phenyl or phenoxy;
R2 is hydrogen;
alkyl, alkenyl or alkynyl;
or a saturatedy,or unsaturated ring which, in addition to carbon atoms, can also contain hetero atoms as ring members are described.
15 Citations
23 Claims
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1. A compound of formula I
wherein n is 0, 1, 2, 3 or 4, or, when R1 is nitro or cyano, n is 1 or 2, and wherein R1 can be the same or different if n is greater than 1; -
X is O or S;
Y is a five-membered heteroaromatic ring which has 1-3 nitrogens and 2-4 carbons or 1-2 nitrogens, 1 oxygen or 1 sulfur, and 2-3 carbons which can be substituted with one or two radicals selected from the group consisting of Cl, CH3, CF3 and OCH3;
R1 is nitro;
cyano;
halogen;
C1-C4-alkyl;
C1-C4-haloalkyl;
C1-C4-alkoxy;
C1-C4-haloalkoxy;
C1-C4-alkylthio;
phenyl or phenoxy, the aromatic rings may carry one to five halogen atoms or one to three of the following radicals selected from the group consisting of halogen, C1-C4-alkyl;
C1-C4-haloalkyl;
C1-C4-alkoxy;
C1-C4-haloalkoxy and C1-C4-alkylthio;
or, if n is greater than 1, a 1,3-butadiene-1,4-diyl group which is bonded to two adjacent C atoms of the phenyl radical and which may carry one to four halogen atoms or one or two of the following radicals selected from the group consisting of halogen, nitro, cyano, C1-C4-alkyl;
C1-C4-haloalkyl;
C1-C4-alkoxy;
C1-C4-haloalkoxy and C1-C4-alkylthio;
R2 is unsubstituted or substituted C1-C4 alkyl, unsubstituted or substituted C3-C6 cycloalkyl, or unsubstituted or substituted phenyl, cyano, acetyl or unsubstituted or substituted aromatic heterocycles containing one to three nitrogen and/or an oxygen or sulfur atom. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 17, 22, 23)
wherein n is 0, 1, 2, 3, or 4, or when R1 is nitro or cyano, n is 1 or 2, and wherein R1 can be the same or different if n is greater than 1; X is O or S;
Y is selected from the group consisting of 3-isoxazolyl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 2-oxazolyl, 2-thiazolyl, 4-thiazolyl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-5-yl, 1, 2, 4, triazol-3-yl;
1,3,4-oxadiazol-2-yl;
which can be substituted with one or two radicals selected from the group consisting of Cl, CH3, CF3 and OCH3;
R1 is nitro;
cyano;
halogen;
C1-C4-alkyl;
C1-C4-haloalkyl;
C1-C4-alkoxy;
C1-C4-haloalkoxy;
C1-C4-alkylthio;
phenyl or phenoxy, wherein the aromatic rings may carry one to five halogen atoms or one to three radicals selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and C1-C4-alkylthio;
or, if n is greater than 1, a 1,3-butadiene-1,4-diyl group which is bonded to two adjacent C atoms of the phenyl radical and which may carry one to four halogen atoms or one or two radicals selected from the group consisting of halogen, nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and C1-C4-alkylthio;
R2 is unsubstituted or substituted alkyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted phenyl, cyano, acetyl or unsubstituted or substituted aromatic heterocycles containing one to three nitrogen and/or an oxygen or sulfur atom.
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3. The compound as claimed in claim 2, wherein Y is 3-isoxazolyl, which can be substituted with one or two radicals selected from the group consisting of Cl, CH3, CF3 and OCH3.
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4. The compound as claimed in claim 2, wherein Y is 1-pyrazolyl, which can be substituted with one or two radicals selected from the group consisting of Cl, CH3, CF3 and OCH3.
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5. The compound as claimed in claim 2, wherein Y is 3-pyrazolyl, which can be substituted with one or two radicals selected from the group consisting of Cl, CH3, CF3 and OCH3.
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6. The compound as claimed in claim 2, wherein Y is 4-pyrazolyl, which can be substituted with one or two radicals selected from the group consisting of Cl, CH3, CF3 and OCH3.
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7. The compound as claimed in claim 2, wherein Y is 2-oxazolyl, which can be substituted with one or two radicals selected from the group consisting of Cl, CH3, CF3 and OCH3.
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8. The compound as claimed in claim 2, wherein Y is 2-thiazolyl, which can be substituted with one or two radicals selected from the group consisting of Cl, CH3, CF3 and OCH3.
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9. The compound as claimed in claim 2, wherein Y is 4-thiazolyl, which can be substituted with one or two radicals selected from the group consisting of Cl, CH3, CF3 and OCH3.
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10. The compound as claimed in claim 2, wherein Y is 1,2,4-oxadiazol-5-yl, which can be substituted with one or two radicals selected from the group consisting of Cl, CH3, CF3 and OCH3.
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11. The compound as claimed in claim 2, wherein Y is 1,2,4-thiadiazol-5-yl, which can be substituted with one or two radicals selected from the group consisting of Cl, CH3, CF3 and OCH3.
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12. The compound as claimed in claim 2, wherein Y is 1,2,4-oxadiazol-2-yl, which can be substituted with one or two radicals selected from the group consisting of Cl, CH3, CF3 and OCH3.
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13. A composition for controlling harmful fungi, comprising a fungicidal amount of a compound of formula I according to claim 1 and an inert carrier.
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14. A composition for controlling harmful insects, arachnids and nematodes comprising an effective amount of a compound of formula I according to claim 1 and an inert carrier.
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17. A compound of the formula I, as claimed in claim 1,
wherein n is 0, 1, 2, 3, or 4, or, when R1 is nitro or cyano, n is 1 or 2, and wherein R1 can be the same or different if n is greater than 1; -
X is O or S;
Y is 1,2,4-triazol-3-yl, which may be substituted with one or two radicals selected from the group consisting of Cl, CH3, CF3 and OCH3;
R1 is nitro;
cyano;
halogen;
C1-C4-alkyl;
C1-C4-haloalkyl;
C1-C4-alkoxy;
C1-C4-haloalkoxy;
C1-C4-alkylthio;
phenyl or phenoxy, wherein the aromatic rings can carry one to five halogen atoms or one to three radicals selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and C1-C4-alkylthio;
or, if n is greater than 1, a 1,3-butadiene-1,4-diyl group which is bonded to two adjacent C atoms of the phenyl radical and which may carry one to four halogen atoms or one or two radicals selected from the group consisting of halogen, nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and C1-C4-alkylthio;
R2 is unsubstituted or substituted alkyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted phenyl, cyano, acetyl or unsubstituted or substituted aromatic heterocycles containing one to three nitrogen and/or an oxygen or sulfur atom.
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22. The compound of formula I according to claim 1, wherein Y is selected from the group consisting of 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 1-imidazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl, 1,2,4-triazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl, 1,2,3-triazol-5-yl and 1,2,3-triazol-4-yl.
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23. The compound of formula I according to claim 1, wherein Y is selected from the group consisting of 3-isoxazolyl, 3-pyrazolyl, 4-pyrazolyl-2-oxazolyl, 2-thiazolyl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl.
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15. A compound of formula I:
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wherein n is 0, 1, 2, 3 or 4, or, when R1 is nitro or cyano, n is 1 or 2, and wherein R1 can be the same or different if n is greater than 1, R1 is nitro, cyano, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, phenyl or phenoxy which may have 1 to 5 halogen atoms or 1 to 3 of the following radicals;
halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C1-C4 alkylthio;
or, if n is greater than 1, a 1,3-butadiene-1,4-diyl group which is bonded to two adjacent C atoms of the phenyl radical and which may carry one to four halogen atoms or one or two of the following radicals;
halogen, nitro, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C1-C4 alkylthio;
R2 is unsubstituted or substituted alkyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted phenyl, cyano, acetyl or unsubstituted or substituted aromatic heterocycles containing one to three nitrogen and/or an oxygen or sulfur atom.- View Dependent Claims (16)
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18. A process for controlling harmful fungi, which comprises treating the harmful fungi, their environment or the plants or materials to be kept free of harmful fungi with a fungicidally effective amount of a compound of formula I
wherein n is 0, 1, 2, 3, or 4, or, when R1 is nitro or cyano, n is 1 or 2, and wherein R1 can be the same or different if n is greater than 1; -
X is O or S;
Y is a five-membered heteroaromatic ring which has 1-3 nitrogens and 2-4 carbons or 1-2 nitrogens, 1 oxygen or 1 sulfur, and 2-3 carbons which can be substituted with one or two radicals selected from the group consisting of Cl, CH3, CF3 and OCH3;
R1 is nitro;
cyano;
halogen;
C1-C4-alkyl;
C1-C4-haloalkyl;
C1-C4-alkoxy;
C1-C4-haloalkoxy;
C1-C4-alkylthio;
phenyl or phenoxy, the aromatic rings may carry one to five halogen atoms or one to three radicals selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and C1-C4-alkylthio;
or, if n is greater than 1, a 1,3-butadiene-1,4-diyl group which is bonded to two adjacent C atoms of the phenyl radical and which may carry one to four halogen atoms or one or two radicals selected from the group consisting of halogen, nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and C1-C4-alkylthio;
R2 is unsubstituted or substituted alkyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted phenyl, cyano, acetyl or unsubstituted or substituted aromatic heterocycles containing one to three nitrogen and/or an oxygen or sulfur atom.
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19. A compound of formula I:
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wherein n is 0 or 1, and wherein R1 is nitro, cyano, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, phenyl or phenoxy which may have 1 to 5 halogen atoms or 1 to 3 of the following radicals;
halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C1-C4 alkylthio;
or, if n is greater than 1, a 1,3-butadiene-1,4-diyl group which is bonded to two adjacent C atoms of the phenyl radical and which may carry one to four halogen atoms or one or two of the following radicals;
halogen, nitro, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C1-C4 alkylthio;
R2 is 4-Cl—
C6H4.
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20. A compound of formula I
wherein n is 0, 1, 2, 3, or 4, or, when R1 is nitro or cyano, n is 1 or 2, and wherein R1 can be the same or different if n is greater than 1; -
X is O or S;
Y is a 1,2,4-triazole;
R1 is nitro;
cyano;
halogen;
C1-C4-alkyl;
C1-C4-haloalkyl;
C1-C4-alkoxy;
C1-C4-haloalkoxy;
C1-C4-alkylthio;
phenyl or phenoxy, the aromatic rings may carry one to five halogen atoms or one to three radicals selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and C1-C4-alkylthio;
or, if n is greater than 1, a 1,3-butadiene-1,4-diyl group which is bonded to two adjacent C atoms of the phenyl radical and which may carry one to four halogen atoms or one or two radicals selected from the group consisting of halogen, nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and C1-C4-alkylthio;
R2 is unsubstituted or substituted phenyl.
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21. A compound of the formula
Specification
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Current AssigneeBASF AG (BASF SE)
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Original AssigneeBASF AG (BASF SE)
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InventorsWingert, Horst, Doetzer, Reinhard, Koenig, Hartmann, Grammenos, Wassilios, Ammermann, Eberhard, Sauter, Hubert, Lorenz, Gisela, Bayer, Herbert, Oberdorf, Klaus, Kirstgen, Reinhard, Harries, Volker
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Primary Examiner(s)AULAKH, CHARANJIT
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Application NumberUS09/409,339Time in Patent Office1,412 DaysField of Search548/264.4, 548/263.4, 548/136, 548/143, 548/187, 548/225, 548/243, 548/366.1, 548/370.1, 514/384, 514/363, 514/364, 514/369, 514/376, 514/380, 514/407US Class Current514/384CPC Class CodesA01N 37/50 the nitrogen atom being dou...A01N 43/50 1,3-Diazoles; Hydrogenated ...A01N 43/56 1,2-Diazoles; Hydrogenated ...A01N 43/653 1,2,4-Triazoles; Hydrogenat...A01N 43/74 five-membered rings with on...A01N 43/80 five-membered rings with on...A01N 43/82 five-membered rings with th...C07D 231/18 One oxygen or sulfur atomC07D 231/22 with aryl radicals attached...C07D 249/12 Oxygen or sulfur atomsC07D 261/12 Oxygen atomsC07D 263/38 attached in position 2C07D 271/113 with oxygen, sulfur or nitr...C07D 277/34 Oxygen atomsC07D 277/36 Sulfur atomsC07D 285/08 1,2,4-Thiadiazoles; Hydroge...
