Cycloalkylalkanecarboxamides and their preparation and use
First Claim
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1. A cycloalkylalkanecarboxamide of the formula I where the substituents have the following meanings:
- A is a substituted C3-C6-cycloalkyl;
R1 is C1-C6-alkyl or C2-C6-alkenyl, it being possible for these radicals to be partially or fully halogenated and/or to have attached to them one or two of the following groups;
C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkoxycarbonyl, C3-C6-cycloalkyl and phenyl, it being possible for the phenyl to be partially or fully halogenated and/or have attached to it one to three of the following radicals;
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C3-C6-cycloalkyl or heterocyclyl;
R2, R3 and R4 are hydrogen or, independently of this meaning, have one of the meanings of the radical R1;
n is 0;
Y is cyano;
W is phenyl, naphthyl or heteroaryl which can have attached to it one to three of the following groups;
nitro, halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C3-C6-cycloalkyl and C1-C4-alkoxycarbonyl.
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Abstract
The present invention relates to novel cycloalkylalkane-carboxamides of the formula I
where the substituents have the following meanings:
A is C3-C6-cycloalkyl;
R1 is C1-C6-alkyl or C2-C6-alkenyl;
R2, R3 and R4 are hydrogen or, independently of this meaning, have one of the meanings of the radical R1;
n is 0 or 1;
Y is cyano or halogen;
w is phenyl, naphthyl or heteroaryl.
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Citations
17 Claims
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1. A cycloalkylalkanecarboxamide of the formula I
where the substituents have the following meanings: -
A is a substituted C3-C6-cycloalkyl;
R1 is C1-C6-alkyl or C2-C6-alkenyl, it being possible for these radicals to be partially or fully halogenated and/or to have attached to them one or two of the following groups;
C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkoxycarbonyl, C3-C6-cycloalkyl and phenyl, it being possible for the phenyl to be partially or fully halogenated and/or have attached to it one to three of the following radicals;
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C3-C6-cycloalkyl or heterocyclyl;
R2, R3 and R4 are hydrogen or, independently of this meaning, have one of the meanings of the radical R1;
n is 0;
Y is cyano;
W is phenyl, naphthyl or heteroaryl which can have attached to it one to three of the following groups;
nitro, halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C3-C6-cycloalkyl and C1-C4-alkoxycarbonyl.- View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17)
A is C3-C6-cycloalkyl which has attached to it one to three substituents selected from the group consisting of halogen and C1-C3-alkyl. -
3. A cycloalkylalkanecarboxamide of the formula I as claimed in claim 1 where
A is C3-C6-cycloalkyl which is methylated. -
4. A cycloalkylalkanecarboxamide of the formula I as claimed in claim 1 where
A is C3-C6-cycloalkyl which carries the methyl substituent at the carbon linking the cycloalkane ring with the rest of the molecule. -
5. A cycloalkylalkanecarboxamide of the formula I as claimed in claim 1 where
A is cyclopropyl which can have attached to it one to three substituents selected from the group consisting of halogen and C1-C3-alkyl. -
6. A cycloalkylalkanecarboxamide of the formula I as claimed in claim 1, where A is cyclopropyl which is substituted by two chlorine atoms.
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7. A cycloalkylalkanecarboxamide of the formula I as claimed in claim 1, where A is cyclopropyl which is substituted by an alkyl group on the carbon atom of the bonding site of the cyclopropane ring with the remainder of the molecule.
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8. A cycloalkylalkanecarboxamide of the formula I as claimed in claim 1 where
R1 is methyl and R2, R3 and R4 are hydrogen or methyl. -
9. A cycloalkylalkanecarboxamide of the formula I as claimed in claim 1 where
W is phenyl, which can have attached to it one to three of the following groups: - nitro, halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C3-C6-cycloalkyl and C1-C4-alkoxycarbonyl.
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10. A cycloalkylalkanecarboxamide of the formula I as claimed in claim 1 where
W is naphthyl, which can have attached to it one to three of the following groups: - nitro, halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C3-C6-cycloalkyl and C1-C4-alkoxycarbonyl.
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11. A process for the preparation of a cycloalkylalkanecarboxamide of the formula I as claimed in claim 1,
which comprises reacting a carboxylic acid derivative of the formula II where the radicals A, Y, R3 and R4 and also n have the meanings given in claim 1, and X is a nucleophilically exchangeable radical with an amine of the formula III where the radicals W, R1 and R2 have the meanings given in claim 1. -
12. A carboxylic acid derivative of the formula II
where X is a nucleophilically exchangeable radical; and A, n, R3, R4 and Y have the meanings given in claim 1.
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13. A carboxylic acid derivative of the formula II as claimed in claim 12, where
A is cyclopropyl which is substituted by two chlorine atoms. -
14. A carbocyclic acid derivative of the formula II as claimed in claim 12 where A is cyclopropyl which has attached to it one to three substituents selected from the group consisting of chlorine and/or C1-C3-alkyl.
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15. A carboxylic acid derivative of the formula II as claimed in claim 12, where A is cyclopropyl which is substituted by an alkyl group on the carbon atom of the bonding site of the cyclopropane ring with the remainder of the molecule.
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16. A composition comprising such an amount of at least one cycloalkylalkanecarboxamide of the formula I as claimed in claim 1 that it is effective for controlling harmful fungi and at least one inert liquid and/or solid carrier and, if appropriate, at least one surfactant.
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17. A method of controlling harmful fungi, which comprises treating the harmful fungi, their environment or the plants, areas, materials or spaces to be kept free from them with an effective amount of a cycloalkylalkanecarboxamide of the formula I as claimed in claim 1.
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Specification
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Current AssigneeBASF AG (BASF SE)
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Original AssigneeBASF AG (BASF SE)
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InventorsWetterich, Frank, Strathmann, Siegfried, Ammermann, Eberhard, Rose, Ingo, Lorenz, Gisela, Eicken, Karl
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Primary Examiner(s)Solola, T A
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Assistant Examiner(s)MURRAY, JOSEPH H
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Application NumberUS09/867,524Publication NumberTime in Patent Office390 DaysField of Search504/312, 558/445US Class Current504/312CPC Class CodesA01N 37/34 NitrilesC07C 255/31 having cyano groups bound t...C07C 255/58 containing cyano groups and...C07C 2601/02 with a three-membered ringC07C 2601/08 the ring being saturated
