Information
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Patent Grant
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4730051
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Patent Number
4,730,051
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Date Filed
Wednesday, January 15, 198638 years ago
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Date Issued
Tuesday, March 8, 198836 years ago
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Inventors
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Original Assignees
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Examiners
Agents
- Stiefel, Gross, Kurland & Pavane
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CPC
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US Classifications
Field of Search
US
- 546 316
- 546 291
- 071 84
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International Classifications
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Abstract
A compounds of the general formula (I): ##STR1## wherein R.sup.1 is alkyl, lower alkenyl, lower alkynyl, aralkyl, haloalkyl, lower alkoxy-lower alkyl, lower alkylthio-lower alkyl or lower alkoxycarbonyl-lower alkyl group; R.sup.2 is aryl group which may be substituted by one or more groups of halogen atom, lower alkyl, lower alkoxy, lower alkoxycarbonyl, trifluoromethyl, cyano and nitro group; R.sup.3 and R.sup.4 are, the same or different, lower alkyl, aralkyl, haloalkyl or cycloalkyl, or aryl group which may be substituted by one or more groups of halogen atom, lower alkyl, lower alkoxy, trifluoromethyl, cyano or nitro group; R.sup.5 is hydrogen atom, halogen atom, lower alkyl, phenyl which may be substituted or aralkyl which may be substituted; or R.sup.4 and R.sup.5 may be combined to form a group of --(CH.sub.2).sub.n - in which n is 3 or 4, or its 1-oxide or addition salt. which is useful as a plant growth inhibitory agent.
Description
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention is concerned with new 4-substituted-oxy-3-pyridinecarboxamide compounds or 1-oxide thereof and their addition salt, which show plant growth inhibitory activity.
2. Description of the Prior Art
As far as the inventors know, there are no reports on 2,6-disubstituted-4-(substituted-oxy)-3-pyridinecarboxamide compounds and 2,6-disubstituted-4-(substituted-oxy)-3-pyridinecarboxamide 1-oxides and their addition salts, as shown by the formula (I) and (I').
SUMMARY OF THE INVENTION
The present invention relates to compounds of the general formula (I) and 1-oxides of the general formula (I'), and their addition salts: ##STR2## wherein R.sup.1 is alkyl, lower alkenyl, lower alkynyl, aralkyl, haloalkyl, lower alkoxy-lower alkyl, lower alkylthio-lower alkyl or lower alkoxycarbonyl-lower alkyl; R.sup.2 is an aryl group which may be substituted by one or more groups of halogen atom, lower alkyl, lower alkoxy, lower alkoxycarbonyl, trifluoromethyl, cyano and nitro group; R.sup.3 and R.sup.4 are, the same or different, lower alkyl, aralkyl, haloalkyl or cycloalkyl, or aryl group which may be substituted by halogen atom, lower alkyl, lower alkoxy, trifluoromethyl, cyano or nitro; R.sup.5 is hydrogen atom, halogen atom, lower alkyl, phenyl which may be substituted or aralkyl which may be substituted; or R.sup.4 and R.sup.5 may be combined to form a group of --(CH.sub.2).sub.n -- (n is 3 or 4).
In this invention, alkyl group includes linear and branched hydrocarbon such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, isopentyl, hexyl or octyl, and also includes cycloalkyl alkyl such as cyclohexylmethyl or cyclopropylmethyl.
The term "lower" used in the invention is intended to mean up to 6 carbon atoms. Specifically, there may be mentioned, as lower alkyl groups, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tertiary butyl, pentyl or isopentyl; as lower alkenyl and lower alkynyl groups, allyl, 2-methyl-2-propenyl, but-2-enyl, pent-2-enyl or 2-propynyl.
Examples of lower alkoxy-lower alkyl and lower alkylthio-lower alkyl groups include methoxyethyl, ethoxyethyl, methoxypropyl, ethoxypropyl, methylthioethyl, ethylthioethyl and the like.
Examples of lower alkoxycarbonyl-lower alkyl groups include methoxycarbonylmethyl, ethoxycarbonylmethyl, 1-methoxycarbonylethyl, propoxycarbonylmethyl and the like.
Examples of lower alkoxy groups include methoxy, ethoxy, propoxy and the like.
Examples of lower alkoxycarbonyl groups include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl and the like.
Examples of aralkyl groups include benzyl, 2-phenylethyl, 3-phenylpropyl, 4-phenylbutyl and the like, which may be substituted on the aromatic nucleus by lower alkyl group having 1-3 carbon atoms, trifluoromethyl group or halogen atom.
Examples of haloalkyl groups include trifluoromethyl, difluoromethyl, fluoromethyl, chloromethyl, chloroethyl, chloropropyl, bromoethyl and the like.
Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like.
Halogen atoms include chlorine, bromine, fluorine and iodine atoms.
Examples of aryl groups include phenyl and naphthyl.
Then, interesting compounds included in this invention are as follows:
4-butoxy-N-(2,6-diethylphenyl)-2,6-dimethyl-3-pyridinecarboxamide,
4-ethoxy-2,6-dimethyl-N-phenyl-3-pyridinecarboxamide,
4-allyloxy-2,6-dimethyl-N-phenyl-3-pyridinecarboxamide,
4-benzyloxy-2,6-dimethyl-N-phenyl-3-pyridinecarboxamide,
4-methoxycarbonylmethoxy-2,6-dimethyl-N-phenyl-3-pyridinecarboxamide,
N-(2,6-diethylphenyl)-2,6-dimethyl-4-propoxy-3-pyridine-carboxamide,
4-benzyloxy-N-(2,6-diethylphenyl)-2,6-dimethyl-3-pyridinecarboxamide,
N-(2,6-diethylphenyl)-2,6-dimethyl-4-phenethyloxy-3-pyridinecarboxamide,
5-bromo-4-butoxy-N-(2,6-diethylphenyl)-2,6-dimethyl-3-pyridinecarboxamide,
N-(2-chlorophenyl)-2,6-dimethyl-4-propoxy-3-pyridinecarboxamide,
2,6-dimethyl-N-(2,3-dimethylphenyl)-4-propoxy-3-pyridinecarboxamide,
2,6-dimethyl-N-(2-methylphenyl)-4-propoxy-3-pyridinecarboxamide,
2,6-dimethyl-N-(2,6-dimethylphenyl)-4-propoxy-3-pyridinecarboxamide,
4-ethoxy-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide,
4-butoxy-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide,
2,6-dimethyl-N-(2,3-dimethylphenyl)-4-(2-propynyloxy)-3-pyridinecarboxamide
4-allyloxy-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide,
4-methoxy-2,6-dimethyl-N-phenyl-3-pyridinecarboxamide,
2,6-dimethyl-N-phenyl-4-propoxy-3-pyridinecarboxamide,
4-butoxy-2,6-dimethyl-N-phenyl-3-pyridinecarboxamide,
4-isobutoxy-2,6-dimethyl-N-phenyl-3-pyridinecarboxamide,
2,6-dimethyl-4-pentyloxy-N-phenyl-3-pyridinecarboxamide,
4-isopentyloxy-2,6-dimethyl-N-phenyl-3-pyridinecarboxamide,
4-hexyloxy-2,6-dimethyl-N-phenyl-3-pyridinecarboxamide,
2,6-dimethyl-N-phenyl-4-(2-propynyloxy)-3-pyridinecarboxamide,
5-bromo-2,6-dimethyl-N-phenyl-4-benzyloxy-3-pyridinecarboxamide,
2,6-dimethyl-N-phenyl-4-(2-phenylethoxy)-3-pyridinecarboxamide,
2,6-dimethyl-N-phenyl-4-(3-phenylpropoxy)-3-pyridinecarboxamide,
2,6-dimethyl-N-phenyl-4-(4-phenylbutoxy)-3-pyridinecarboxamide,
4-(3-chlorobenzyloxy)-2,6-dimethyl-N-phenyl-3-pyridinecarboxamide,
4-(4-chlorobenzyloxy)-2,6-dimethyl-N-phenyl-3-pyridinecarboxamide,
2,6-dimethyl-4-(3-methylbenzyloxy)-N-phenyl-3-pyridinecarboxamide,
2,6-dimethyl-4-(4-methylbenzyloxy)-N-phenyl-3-pyridinecarboxamide,
N-(2-chlorophenyl)-4-butoxy-2,6-dimethyl-3-pyridinecarboxamide,
N-(2-chlorophenyl)-4-hexyloxy-2,6-dimethyl-3-pyridinecarboxamide,
4-benzyloxy-N-(2-chlorophenyl)-2,6-dimethyl-3-pyridinecarboxamide,
4-(4-chlorobenzyloxy)-N-(2-chlorophenyl)-2,6-dimethyl-3-pyridinecarboxamide
N-(2-chlorophenyl)-2,6-dimethyl-4-(4-methylbenzyloxy)-3-pyridinecarboxamide
N-(2-chloro-6-methylphenyl)-2,6-dimethyl-4-propoxy-3-pyridinecarboxamide,
N-(2-chloro-6-methylphenyl)-4-butoxy-2,6-dimethyl-3-pyridinecarboxamide,
N-(2-chloro-6-methylphenyl)-4-hexyloxy-2,6-dimethyl-3-pyridinecarboxamide,
4-benzyloxy-N-(2-chloro-6-methylphenyl)-2,6-dimethyl-3-pyridinecarboxamide,
N-(2,6-diethylphenyl)-4-methoxy-2,6-dimethyl-3-pyridinecarboxamide,
4-ethoxy-N-(2,6-diethylphenyl)-2,6-dimethyl-3-pyridinecarboxamide,
N-(2,6-diethylphenyl)-4-isobutoxy-2,6-dimethyl-3-pyridinecarboxamide,
N-(2,6-diethylphenyl)-2,6-dimethyl-4-pentyloxy-3-pyridinecarboxamide,
N-(2,6-diethylphenyl)-4-isopentyloxy-2,6-dimethyl-3-pyridinecarboxamide,
N-(2,6-diethylphenyl)-4-hexyloxy-2,6-dimethyl-3-pyridinecarboxamide,
4-allyloxy-N-(2,6-diethylphenyl)-2,6-dimethyl-3-pyridinecarboxamide,
N-(2,6-diethylphenyl)-2,6-dimethyl-4-(2-propynyloxy)-3-pyridinecarboxamide,
N-(2,6-diethylphenyl)-4-methoxycarbonylmethoxy-2,6-dimethyl-3-pyridinecarboxamide,
N-(2,6-diethylphenyl)-2,6-dimethyl-4-(3-phenylpropoxy)-3-pyridinecarboxamide,
N-(2,6-diethylphenyl)-2,6-dimethyl-4-(4-phenylbutoxy)-3-pyridinecarboxamide
4-(3-chlorobenzyloxy)-N-(2,6-diethylphenyl)-2,6-dimethyl-3-pyridinecarboxamide,
4-(4-chlorobenzyloxy)-N-(2,6-diethylphenyl)-2,6-dimethyl-3-pyridinecarboxamide,
N-(2,6-diethylphenyl)-2,6-dimethyl-4-(3-methylbenzyloxy)-3-pyridinecarboxamide,
N-(2,6-diethylphenyl)-2,6-dimethyl-4-(4-methylbenzyloxy)-3-pyridinecarboxamide,
N-(2-ethyl-6-methylphenyl)-4-methoxy-2,6-dimethyl-3-pyridinecarboxamide,
4-ethoxy-N-(2-ethyl-6-methylphenyl)-2,6-dimethyl-3-pyridinecarboxamide,
N-(2-ethyl-6-methylphenyl)-2,6-dimethyl-4-propoxy-3-pyridinecarboxamide,
4-butoxy-N-(2-ethyl-6-methylphenyl)-2,6-dimethyl-3-pyridinecarboxamide,
N-(2-ethyl-6-methylphenyl)-4-isobutoxy-2,6-dimethyl-3-pyridinecarboxamide,
N-(2-ethyl-6-methylphenyl)-4-hexyloxy-2,6-dimethyl-3-pyridinecarboxamide,
4-allyloxy-N-(2-ethyl-6-methylphenyl)-2,6-dimethyl-3-pyridinecarboxamide,
N-(2-ethyl-6-methylphenyl)-2,6-dimethyl-4-(2-propynyloxy)-3-pyridinecarboxamide,
4-benzyloxy-N-(2-ethyl-6-methylphenyl)-2,6-dimethyl-3-pyridinecarboxamide,
4-(4-chlorobenzyloxy)-N-(2-ethyl-6-methylphenyl)-2,6-dimethyl-3-pyridinecarboxamide,
N-(2-ethyl-6-methylphenyl)-2,6-dimethyl-4-(4-methylbenzyloxy)-3-pyridinecarboxamide,
4-ethoxy-2,6-dimethyl-N-(2-methylphenyl)-3-pyridinecarboxamide,
4-butoxy-2,6-dimethyl-N-(2-methylphenyl)-3-pyridinecarboxamide,
4-isobutoxy-2,6-dimethyl-N-(2-methylphenyl)-3-pyridinecarboxamide,
4-hexyloxy-2,6-dimethyl-N-(2-methylphenyl)-3-pyridinecarboxamide,
4-allyloxy-2,6-dimethyl-N-(2-methylphenyl)-3-pyridinecarboxamide,
4-benzyloxy-2,6-dimethyl-N-(2-methylphenyl)-3-pyridinecarboxamide,
4-(4-chlorobenzyloxy)-2,6-dimethyl-N-(2-methylphenyl)-3-pyridinecarboxamide
2,6-dimethyl-4-(4-methylbenzyloxy)-N-(2-methylphenyl)-3-pyridinecarboxamide
4-isobutoxy-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide,
4-hexyloxy-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide,
4-benzyloxy-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide,
4-(4-chlorobenzyloxy)-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide,
2,6-dimethyl-4-(4-methylbenzyloxy)-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide,
4-methoxy-2,6-dimethyl-N-(2,6-dimethylphenyl)-3-pyridinecarboxamide,
4-ethoxy-2,6-dimethyl-N-(2,6-dimethylphenyl)-3-pyridinecarboxamide,
4-butoxy-2,6-dimethyl-N-(2,6-dimethylphenyl)-3-pyridinecarboxamide,
4-butoxy-2,6-dimethyl-N-(2,5-dimethylphenyl)-3-pyridinecarboxamide,
4-isobutoxy-2,6-dimethyl-N-(2,6-dimethylphenyl)-3-pyridinecarboxamide,
2,6-dimethyl-N-(2,6-dimethylphenyl)-4-pentyloxy-3-pyridinecarboxamide,
4-isopentyloxy-2,6-dimethyl-N-(2,6-dimethylphenyl)-3-pyridinecarboxamide,
4-hexyloxy-2,6-dimethyl-N-(2,6-dimethylphenyl)-3-pyridinecarboxamide,
4-allyloxy-2,6-dimethyl-N-(2,6-dimethylphenyl)-3-pyridinecarboxamide,
2,6-dimethyl-N-(2,6-dimethylphenyl)-4-(2-propynyloxy)-3-pyridinecarboxamide
4-benzyloxy-2,6-dimethyl-N-(2,6-dimethylphenyl)-3-pyridinecarboxamide,
4-(4-chlorobenzyloxy)-2,6-dimethyl-N-(2,6-dimethylphenyl)-3-pyridinecarboxamide,
2,6-dimethyl-4-(4-methylbenzyloxy)-N-(2,6-dimethylphenyl)-3-pyridinecarboxamide,
N-(2,6-diisopropylphenyl)-2,6-dimethyl-4-propoxy-3-pyridinecarboxamide,
4-butoxy-N-(2,6-diisopropylphenyl)-2,6-dimethyl-3-pyridinecarboxamide,
N-(2,6-diisopropylphenyl)-4-hexyloxy-2,6-dimethyl-3-pyridinecarboxamide,
4-allyloxy-N-(2,6-diisopropylphenyl)-2,6-dimethyl-3-pyridinecarboxamide,
4-benzyloxy-N-(2,6-diisopropylphenyl)-2,6-dimethyl-3-pyridinecarboxamide,
4-(4-chlorobenzyloxy)-N-(2,6-diisopropylphenyl)-2,6-dimethyl-3-pyridinecarboxamide,
N-(2,6-diisopropylphenyl)-2,6-dimethyl-4-(4-methylbenzyloxy)-3-pyridinecarboxamide,
5-bromo-N-(2,6-diethylphenyl)-2,6-dimethyl-4-propoxy-3-pyridinecarboxamide,
5-bromo-N-(2,6-diethylphenyl)-4-isobutoxy-2,6-dimethyl-3-pyridinecarboxamide,
5-bromo-N-(2,6-diethylphenyl)-2,6-dimethyl-4-pentyloxy-3-pyridinecarboxamide,
5-bromo-N-(2,6-diethylphenyl)-4-isopentyloxy-2,6-dimethyl-3-pyridinecarboxamide,
5-bromo-N-(2,6-diethylphenyl)-4-hexyloxy-2,6-dimethyl-3-pyridinecarboxamide
4-allyloxy-5-bromo-N-(2,6-diethylphenyl)-2,6-dimethyl-3-pyridinecarboxamide
5-bromo-N-(2-ethyl-6-methylphenyl)-2,6-dimethyl-4-propoxy-3-pyridinecarboxamide,
5-bromo-4-butoxy-N-(2-ethyl-6-methylphenyl)-2,6-dimethyl-3-pyridinecarboxamide,
5-bromo-N-(2-ethyl-6-methylphenyl)-4-hexyloxy-2,6-dimethyl-3-pyridinecarboxamide,
5-bromo-2,6-dimethyl-N-(2,6-dimethylphenyl)-4-propoxy-3-pyridinecarboxamide
5-bromo-4-butoxy-2,6-dimethyl-N-(2,6-dimethylphenyl)-3-pyridinecarboxamide,
5-bromo-4-isobutoxy-2,6-dimethyl-N-(2,6-dimethylphenyl)-3-pyridinecarboxamide,
5-bromo-2,6-dimethyl-N-(2,6-dimethylphenyl)-4-pentyloxy-3-pyridinecarboxamide,
5-bromo-4-isopentyloxy-2,6-dimethyl-N-(2,6-dimethylphenyl)-3-pyridinecarboxamide,
5-bromo-4-hexyloxy-2,6-dimethyl-N-(2,6-dimethylphenyl)-3-pyridinecarboxamide,
4-allyloxy-5-bromo-2,6-dimethyl-N-(2,6-dimethylphenyl)-3-pyridinecarboxamide,
5-bromo-2,6-dimethyl-N-(2,6-dimethylphenyl)-4-(2-propynyloxy)-3-pyridinecarboxamide,
5-bromo-N-(2,6-diisopropylphenyl)-2,6-dimethyl-4-propoxy-3-pyridinecarboxamide,
5-bromo-4-butoxy-N-(2,6-diisopropylphenyl)-2,6-dimethyl-3-pyridinecarboxamide,
5-bromo-4-hexyloxy-N-(2,6-diisopropylphenyl)-2,6-dimethyl-3-pyridinecarboxamide,
4-benzyloxy-5-bromo-N-(2,6-diethylphenyl)-2,6-dimethyl-3-pyridinecarboxamide,
4-benzyloxy-5-bromo-N-(2-ethyl-6-methylphenyl)-2,6-dimethyl-3-pyridinecarboxamide,
4-benzyloxy-5-bromo-2,6-dimethyl-N-(2,6-dimethylphenyl)-3-pyridinecarboxamide,
4-benzyloxy-5-bromo-N-(2,6-diisopropylphenyl)-2,6-dimethyl-3-pyridinecarboxmide,
5-chloro-N-(2,6-diethylphenyl)-2,6-dimethyl-4-propoxy-3-pyridinecarboxamide
4-butoxy-5-chloro-N-(2,6-diethylphenyl)-2,6-dimethyl-3-pyridinecarboxamide,
5-chloro-N-(2,6-diethylphenyl)-4-hexyloxy-2,6-dimethyl-3-pyridinecarboxamide,
4-allyloxy-5-chloro-N-(2,6-diethylphenyl)-2,6-dimethyl-3-pyridinecarboxamide,
4-butoxy-5-chloro-N-(2-ethyl-6-methylphenyl)-2,6-dimethyl-3-pyridinecarboxamide,
5-chloro-N-(2-ethyl-6-methylphenyl)-4-hexyloxy-2,6-dimethyl-3-pyridinecarboxamide,
4-butoxy-5-chloro-2,6-dimethyl-N-(2,6-dimethylphenyl)-3-pyridine carboxamide,
5-chloro-4-hexyloxy-2,6-dimethyl-N-(2,6-dimethylphenyl)-3-pyridinecarboxamide,
4-butoxy-5-chloro-N-(2,6-diisopropylphenyl-2,6-dimethyl-3-pyridinecarboxamide,
5-chloro-4-hexyloxy-N-(2,6-diisopropylphenyl)-2,6-dimethyl-3-pyridinecarboxamide,
2,6-dimethyl-N-(2,3-dimethylphenyl)-4-pentyloxy-3-pyridinecarboxamide,
4-isopentyloxy-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide,
2,6-dimethyl-N-(2,3-dimethylphenyl)-4-octyloxy-3-pyridinecarboxamide,
2,6-dimethyl-N-(2,3-dimethylphenyl)-4-(2-phenylethyloxy)-3-pyridinecarboxamide,
4-cyclohexylmethyloxy-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide,
N-(2,6-diethylphenyl)-4-isopropoxy-2,6-dimethyl-3-pyridinecarboxamide,
4-ethoxycarbonylmethyloxy-N-(2,6-diethylphenyl)-2,6-dimethyl-3-pyridinecarboxamide,
4-(1-ethoxycarbonylethyloxy)-N-(2,6-diethyphenyl)-2,6-dimethyl-3-pyridinecarboxamide,
2,6-dimethyl-N-phenyl-4-propoxy-3-pyridinecarboxamide 1-oxide,
4-butoxy-2,6-dimethyl-N-phenyl-3-pyridinecarboxamide 1-oxide,
2,6-dimethyl-N-(2-methylphenyl)-4-propoxy-3-pyridinecarboxamide 1-oxide,
2,6-dimethyl-N-(2,3-dimethylphenyl)-4-propoxy-3-pyridinecarboxamide 1-oxide,
4-butoxy-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide 1-oxide,
4-isobutoxy-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide 1-oxide,
2,6-dimethyl-N-(2,3-dimethylphenyl)-4-pentyloxy-3-pyridnecarboxamide 1-oxide,
4-isopentyloxy-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide 1-oxide,
4-hexyloxy-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide 1-oxide,
2,6-dimethyl-N-(2,3-dimethylphenyl)-4-octyloxy-3-pyridinecarboxamide 1-oxide,
4-(2-ethoxyethoxy)-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide 1-oxide,
4-allyloxy-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide 1-oxide,
2,6-dimethyl-N-(2,6-dimethylphenyl)-4-propoxy-3-pyridinecarboxamide 1-oxide,
4-ethoxy-N-(2,6-diethylphenyl)-2,6-dimethyl-3-pyridinecarboxamide 1-oxide,
N-(2,6-diethylphenyl)-2,6-dimethyl-4-propoxy-3-pyridinecarboxamide 1-oxide,
N-(2,6-diethylphenyl)-4-isopropoxy-2,6-dimethyl-3-pyridinecarboxamide 1-oxide,
4-butoxy-N-(2,6-diethylphenyl)-2,6-dimethyl-3-pyridinecarboxamide 1-oxide,
N-(2,6-diethylphenyl)-4-isobutoxy-2,6-dimethyl-3-pyridinecarboxamide 1-oxide,
N-(2,6-diethylphenyl)-2,6-dimethyl-4-pentyloxy-3-pyridinecarboxamide 1-oxide,
4-benzyloxy-N-(2,6-diethylphenyl)-2,6-dimethyl-3-pyridinecarboxamide 1-oxide,
4-ethoxycarbonylmethoxy-N-(2,6-diethylphenyl)-2,6-dimethyl-3-pyridinecarboxamide 1-oxide,
4-(1-ethoxycarbonylethoxy)-N-(2,6-diethylphenyl)-2,6-dimethyl-3-pyridinecarboxamide 1-oxide,
N-(2-methoxyphenyl)-2,6-dimethyl-4-propoxy-3-pyridinecarboxamide 1-oxide,
2,6-dimethyl-N-(3-nitrophenyl)-4-propoxy-3-pyridinecarboxamide 1-oxide,
6-methyl-N, 2-diphenyl-4-propoxy-3-pyridinecarboxamide 1-oxide,
5-bromo-N-(2,6-diethylphenyl)-2,6-dimethyl-4-propoxy-3-pyridinecarboxamide 1-oxide,
4-ethoxy-2,6-dimethyl-N-phenyl-3-pyridinecarboxamide 1-oxide,
4-isopropoxy-2,6-dimethyl-N-phenyl-3-pyridinecarboxamide 1-oxide,
4-isobutoxy-2,6-dimethyl-N-phenyl-3-pyridinecarboxamide 1-oxide,
2,6-dimethyl-4-pentyloxy-N-phenyl-3-pyridinecarboxamide 1-oxide,
4-isopentyloxy-2,6-dimethyl-N-phenyl-3-pyridinecarboxamide 1-oxide, 4-allyloxy-2,6-dimethyl-N-phenyl-3-pyridinecarboxamide 1-oxide,
2,6-dimethyl-N-phenyl-4-(2-propynyloxy)-3-pyridinecarboxamide 1-oxide,
4-methoxy-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide 1-oxide,
4-ethoxy-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide 1-oxide,
4-isopropoxy-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide 1-oxide,
2,6-dimethyl-N-(2,3-dimethylphenyl)-4-(2-propynyloxy)-3-pyridinecarboxamide 1-oxide,
4-benzyloxy-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide 1-oxide,
2,6-dimethyl-N-(2,3-dimethylphenyl)-4-(2-phenylethoxy)-3-pyridinecarboxamide 1-oxide,
4-cyclohexylmethoxy-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide 1-oxide,
4-(2-chloroethoxy)-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide 1-oxide,
N-(2,6-diethylphenyl)-4-methoxy-2,6-dimethyl-3-pyridinecarboxamide 1-oxide,
N-(2,6-diethylphenyl)-4-isopentyloxy-2,6-dimethyl-3-pyridinecarboxamide 1-oxide,
4-allyloxy-N-(2,6-diethylphenyl)-2,6-dimethyl-3-pyridinecarboxamide 1-oxide,
N-(2,6-diethylphenyl)-2,6-dimethyl-4-(2-propynyloxy)-3-pyridinecarboxamide 1-oxide,
N-(2,6-diethylphenyl)-2,6-dimethyl-4-(2-phenylethoxy)-3-pyridinecarboxamide 1-oxide,
4-cyclohexylmethoxy-N-(2,6-diethylphenyl)-2,6-dimethyl-3-pyridinecarboxamide 1-oxide,
4-(2-chloroethoxy)-N-(2,6-diethylphenyl)-2,6-dimethyl-3-pyridinecarboxamide 1-oxide,
N-(2-chlorophenyl)-2,6-dimethyl-4-propoxy-3-pyridinecarboxamide 1-oxide,
4-butoxy-N-(3-trifluoromethylphenyl)-2,6-dimethyl-3-pyridinecarboxamide 1-oxide,
N-(2-chloro-6-methylphenyl)-4-isobutyloxy-2,6-dimethyl-3-pyridinecarboxamide 1-oxide,
N-(2-ethyl-6-methylphenyl)-4-isopentyloxy-2,6-dimethyl-3-pyridinecarboxamide 1-oxide,
4-allyloxy-N-(2,6-dichlorophenyl)-2,6-dimethyl-3-pyridinecarboxamide 1-oxide,
N-(4-bromo-2,6-diethylphenyl)-2,6-dimethyl-4-propoxy-3-pyridinecarboxamide 1-oxide,
4-butoxy-N-(4-bromo-2,6-diethylphenyl)-2,6-dimethyl-3-pyridinecarboxamide 1-oxide,
N-(4-bromo-2,6-diethylphenyl)-4-isobutoxy-2,6-dimethyl-3-pyridinecarboxamide 1-oxide,
N-(4-bromo-2,6-diethylphenyl)-2,6-dimethyl-4-pentyloxy-3-pyridinecarboxamide 1-oxide,
N-(4-bromo-2,6-diethylphenyl)-4-isopentyloxy-2,6-dimethyl-3-pyridinecarboxamide 1-oxide,
4-allyloxy-N-(4-bromo-2,6-diethylphenyl)-2,6-dimethyl-3-pyridinecarboxamide 1-oxide,
N-(4-chloro-2,6-diethylphenyl)-2,6-dimethyl-4-propoxy-3-pyridinecarboxamide 1-oxide,
4-butoxy-N-(4-chloro-2,6-diethylphenyl)-2,6-dimethyl-3-pyridinecarboxamide 1-oxide,
N-(4-chloro-2,6-diethylphenyl)-4-isobutoxy-2,6-dimethyl-3-pyridinecarboxamide 1-oxide,
N-(4-chloro-2,6-diethylphenyl)-2,6-dimethyl-4-pentyloxy-3-pyridinecarboxamide 1-oxide,
N-(4-chloro-2,6-diethylphenyl)-4-isopentyloxy-2,6-dimethyl-3-pyridinecarboxamide 1-oxide,
4-allyloxy-N-(4-chloro-2,6-diethylphenyl)-2,6-dimethyl-3-pyridinecarboxamide 1-oxide,
6-methyl-N-(2,3-dimethylphenyl)-2-phenyl-4-propoxy-3-pyridinecarboxamide 1-oxide,
4-butoxy-6-methyl-N-(2,3-dimethylphenyl)-2-phenyl-3-pyridinecarboxamide 1-oxide,
4-isobutoxy-6-methyl-N-(2,3-dimethylphenyl)-2-phenyl-3-pyridinecarboxamide 1-oxide,
4-isopentyloxy-6-methyl-N-(2,3-dimethylphenyl)-2-phenyl-3-pyridinecarboxamide 1-oxide,
4-allyloxy-6-methyl-N-(2,3-dimethylphenyl)-2-phenyl-3-pyridinecarboxamide 1-oxide,
N-(2,6-diethylphenyl)-6-methyl-2-phenyl-4-propoxy-3-pyridinecarboxamide 1-oxide,
4-butoxy-N-(2,6-diethylphenyl)-6-methyl-2-phenyl-3-pyridinecarboxamide 1-oxide,
N-(2,6-diethylphenyl)-4-isobutoxy-6-methyl-2-phenyl-3-pyridinecarboxamide 1-oxide,
N-(2,6-diethylphenyl)-4-isopentyloxy-6-methyl-2-phenyl-3-pyridinecarboxamide 1-oxide,
4-allyloxy-N-(2,6-diethylphenyl)-6-methyl-2-phenyl-3-pyridinecarboxamide 1-oxide,
N-(4-bromo-2,6-diethylphenyl)-6-methyl-6-methyl-2-phenyl-4-propoxy-3-pyridinecarboxamide 1-oxide,
N-(4-bromo-2,6-diethylphenyl)-4-butoxy-6-methyl-2-phenyl-3-pyridinecarboxamide 1-oxide,
5-bromo-N-(2,6-diethylphenyl)-4-isobutoxy-2,6-dimethyl-3-pyridinecarboxamide 1-oxide,
5-bromo-N-(2,6-diethylphenyl)-4-isopentyloxy-2,6-dimethyl-3-pyridinecarboxamide 1-oxide,
5-bromo-N-(4-bromo-2,6-diethylphenyl)-2,6-dimethyl-4-propoxy-3-pyridinecarboxamide 1-oxide,
4-butoxy-5-chloro-N-(2,6-diethylphenyl)-2,6-dimethyl-3-pyridinecarboxamide 1-oxide,
4-allyloxy-5-chloro-N-(2,6-diethylphenyl)-2,6-dimethyl-3-pyridinecarboxamide 1-oxide,
5-chloro-N-(4-chloro-2,6-diethylphenyl)-2,6-dimethyl-4-propoxy-3-pyridinecarboxamide 1-oxide,
2-ethyl-6-methyl-N-(2,3-dimethylphenyl)-4-propoxy-3-pyridinecarboxamide 1-oxide,
4-butoxy-2-ethyl-6-methyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide 1-oxide,
2-ethyl-N-(2,6-diethylphenyl)-6-methyl-4-propoxy-3-pyridinecarboxamide 1-oxide,
2-ethyl-N-(2,6-diethylphenyl)-4-isopropoxy-6-methyl-3-pyridinecarboxamide 1-oxide,
6-methyl-N-(2,3-dimethylphenyl)-4-propoxy-2-propyl-3-pyridinecarboxamide 1-oxide,
4-isopentyloxy-6-methyl-N-(2,3-dimethylphenyl)-2-propyl-3-pyridinecarboxamide 1-oxide,
N-(2,6-diethylphenyl)-6-methyl-4-propoxy-2-propyl-3-pyridinecarboxamide 1-oxide,
4-allyloxy-N-(2,6-diethylphenyl)-6-methyl-2-propyl-3-pyridinecarboxamide 1-oxide,
6-methyl-N-(2,3-dimethylphenyl)-2-phenylmethyl-4-propoxy-3-pyridinecarboxamide 1-oxide,
4-butoxy-6-methyl-N-(2,3-dimethylphenyl)-2-phenylmethyl-3-pyridinecarboxamide 1-oxide,
N-(2,6-diethylphenyl)-6-methyl-2-phenylmethyl-4-propoxy-3-pyridinecarboxamide 1-oxide,
N-(2,6-diethylphenyl)-4-isobutoxy-6-methyl-2-phenylmethyl-3-pyridinecarboxamide 1-oxide,
2-trifluoromethyl-6-methyl-N-(2,3-dimethylphenyl)-4-propoxy-3-pyridinecarboxamide 1-oxide,
2-trifluoromethyl-4-isopentyloxy-6-methyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide 1-oxide,
N-(2,6-diethylphenyl)-2-trifluoromehtyl-6-methyl-4-propoxy-3-pyridinecarboxamide 1-oxide,
4-allyloxy-N-(2,6-diethylphenyl)-2-trifluoromethyl-6-methyl-3-pyridinecarboxamide 1-oxide,
4-butoxy-6-methyl-N-(2,3-dimethylphenyl)-2-propyl-3-pyridinecarboxamide 1-oxide,
2-ethyl-4-isobutoxy-6-methyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide 1-oxide,
4-isobutoxy-6-methyl-N-(2,3-dimethylphenyl)-2-propyl-3-pyridinecarboxamide 1-oxide,
2-ethyl-4-isopentyloxy-6-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide 1-oxide,
4-allyloxy-2-ethyl-6-methyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide 1-oxide,
4-allyloxy-6-methyl-N-(2,3-dimethylphenyl)-2-propyl-3-pyridinecarboxamide 1-oxide,
4-butoxy-2-ethyl-N-(2,6-diethylphenyl)-6-methyl-3-pyridinecarboxamide 1-oxide,
4-butoxy-N-(2,6-diethylphenyl)-6-methyl-2-propyl-3-pyridinecarboxamide 1-oxide,
N-(2,6-diethylphenyl)-4-isobutoxy-6-methyl-2-propyl-3-pyridinecarboxamide 1-oxide,
2-ethyl-N-(2,6-diethylphenyl)-4-isopentyloxy-6-methyl-3-pyridinecarboxamide 1-oxide,
N-(2,6-diethylphenyl)-4-isopentyloxy-6-methyl-2-propyl-3-pyridinecarboxamide 1-oxide,
4-allyloxy-2-ethyl-N-(2,6-diethylphenyl)-6-methyl-3-pyridinecarboxamide 1-oxide,
4-butoxy-2-trifluoromethyl-6-methyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide 1-oxide,
4-isobutoxy-6-methyl-N-(2,3-dimethylphenyl)-2-phenylmethyl-3-pyridinecarboxamide 1-oxide,
2-trifluoromethyl-4-isobutoxy-6-methyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide 1-oxide,
4-isopentyloxy-6-methyl-N-(2,3-dimethylphenyl)-2-phenylmethyl-3-pyridinecarboxamide 1-oxide,
4-allyloxy-6-methyl-N-(2,3-dimethylphenyl)-2-phenylmethyl-3-pyridinecarboxamide 1-oxide,
4-allyloxy-2-trifluoromethyl-6-methyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide 1-oxide,
4-butoxy-N-(2,6-diethylphenyl)-6-methyl-2-phenylmethyl-3-pyridinecarboxamide 1-oxide,
4-butoxy-N-(2,6-diethylphenyl)-2-trifluoromethyl-6-methyl-3-pyridinecarboxamide 1-oxide,
N-(2,6-diethylphenyl)-2-trifluoromethyl-4-isobutoxy-6-methyl-3-pyridinecarboxamide 1-oxide,
N-(2,6-diethylphenyl)-4-isopentyloxy-6-methyl-2-phenylmethyl-3-pyridinecarboxamide 1-oxide,
N-(2,6-diethylphenyl)-2-trifluoromethyl-4-isopentyloxy-6-methyl-3-pyridinecarboxamide 1-oxide,
4-allyloxy-N-(2,6-diethylphenyl)-6-methyl-2-phenylmethyl-3-pyridinecarboxamide 1-oxide,
4-(2-ethylthioethoxy)-N-(2,6-diethylphenyl)-2,6-dimethyl-3-pyridinecarboxamide 1-oxide,
2-cyclohexyl-6-methyl-N-(2,3-dimethylphenyl)-4-propoxy-3-pyridinecarboxamide 1-oxide,
6-methyl-N-(2,3-dimethylphenyl)-2-(2-methylphenyl)-4-propoxy-3-pyridinecarboxamide 1-oxide,
6-methyl-N-(2,3-dimethylphenyl)-2-(3-methylphenyl)-4-propoxy-3-pyridinecarboxamide 1-oxide,
6-methyl-N-(2,3-dimethylphenyl)-2-(4-methylphenyl)-4-propoxy-3-pyridinecarboxamide 1-oxide,
2-(2-chlorophenyl)-N-(2,6-diethylphenyl)-6-methyl-4-propoxy-3-pyridinecarboxamide 1-oxide,
2-(3-chlorophenyl)-N-(2,6-diethylphenyl)-6-methyl-4-propoxy-3-pyridinecarboxamide 1-oxide,
N-(2,6-diethylphenyl)-2-(3-trifluoromethylphenyl)-6-methyl-4-propoxy-3-pyridinecarboxamide 1-oxide,
N-(2,6-diethylphenyl)-2-(4-methoxyphenyl)-6-methyl-4-propoxy-3-pyridinecarboxamide 1-oxide,
2-(3-cyanophenyl)-N-(2,6-diethylphenyl)-6-methyl-4-propoxy-3-pyridinecarboxamide 1-oxide,
N-(2,6-diethylphenyl)-6-methyl-2-(3-nitrophenyl)-4-propoxy-3-pyridinecarboxamide 1-oxide,
N-(2-methoxycarbonylphenyl)-2,6-dimethyl-4-propoxy-3-pyridinecarboxamide 1-oxide,
N-(4-cyanophenyl)-2,6-dimethyl-4-propoxy-3-pyridinecarboxamide 1-oxide,
2,6-dimethyl-N-(2,4,6-trimethylphenyl)-4-propoxy-3-pyridinecarboxamide 1-oxide,
N-(2,6-diethyl-4-methylphenyl)-2,6-dimethyl-4-propoxy-3-pyridinecarboxamide 1-oxide,
N-(2,4,6-triethylphenyl)-2,6-dimethyl-4-propoxy-3-pyridinecarboxamide 1-oxide,
N-(2-methoxyphenyl)-2,6-dimethyl-4-propoxy-3-pyridinecarboxamide,
2,6-dimethyl-N-(3-nitrophenyl)-4-propoxy-3-pyridinecarboxamide,
4-(2-ethoxyethoxy)-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide,
4-(2-chloroethoxy)-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide,
N-(4-bromo-2,6-diethylphenyl)-2,6-dimethyl-4-propoxy-3-pyridinecarboxamide,
6-methyl-N,2-diphenyl-4-propoxy-3-pyridinecarboxamide,
6-methyl-N-(2,3-dimethylphenyl)-2-phenyl-4-propoxy-3-pyridinecarboxamide,
N-(2,6-diethylphenyl)-6-methyl-2-phenyl-4-propoxy-3-pyridinecarboxamide,
N-(4-bromo-2,6-diethylphenyl)-4-butoxy-2,6-dimethyl-3-pyridinecarboxamide,
2-ethyl-N-(2,6-diethylphenyl)-6-methyl-4-propoxy-3-pyridinecarboxamide,
5-bromo-N-(4-bromo-2,6-diethylphenyl)-2,6-dimethyl-4-propoxy-3-pyridinecarboxamide,
N-(2,6-diethylphenyl)-2,5,6-trimethyl-4-propoxy-3-pyridinecarboxamide,
4-butoxy-2,5,6-trimethyl-N-phenyl-3-pyridinecarboxamide,
2,6-diethyl-N-(2,6-diethylphenyl)-4-propoxy-3-pyridinecarboxamide,
N-(2,6-diethylphenyl)-2-methyl-6-phenyl-4-propoxy-3-pyridinecarboxamide,
N-(2,6-diethylphenyl)-5,6,7,8-tetrahydro-2-methyl-4-propoxy-3-quinolinecarboxamide,
6-butyl-N-(2,6-diethylphenyl)-2-methyl-4-propoxy-3-pyridinecarboxamide,
N-(2,6-diethylphenyl)-2,6-dimethyl-4-(2-phenylethyloxy)-3-pyridinecarboxamide 1-oxide,
5-bromo-N-(4-bromo-2,6-diethylphenyl)-2,6-dimethyl-4-propoxy-3-pyridinecarboxamide 1-oxide,
2-ethyl-N-(2,6-diethylphenyl)-6-methyl-4-propoxy-3-pyridinecarboxamide 1-oxide,
N-(2,6-diethylphenyl)-2,5,6-trimethyl-4-propoxy-3-pyridinecarboxamide 1-oxide,
2,6-diethyl-N-(2,6-diethylphenyl)-4-propoxy-3-pyridinecarboxamide 1-oxide,
4-butoxy-2,5,6-trimethyl-N-phenyl-3-pyridinecarboxamide 1-oxide,
6-butyl-N-(2,6-diethylphenyl)-2-methyl-4-propoxy-3-pyridinecarboxamide 1-oxide,
N-(2,6-diethylphenyl)-5,6,7,8-tetrahydro-2-methyl-4-propoxy-3-quinolinecarboxamide 1-oxide,
N-(2,6-diethylphenyl)-4-isobutoxy-5,6-dimethyl-2-propyl-3-pyridinecarboxamide 1-oxide,
6-ethyl-N-(2,6-diethylphenyl)-2-methyl-4-propoxy-3-pyridinecarboxamide 1-oxide,
6-ethyl-2-methyl-N-(2,3-dimethylphenyl)-4-propoxy-3-pyridinecarboxamide 1-oxide,
2,6-diethyl-N-(2,3-dimethylphenyl)-4-propoxy-3-pyridinecarboxamide 1-oxide,
N-(4-bromo-2,6-diethylphenyl)-2,6-diethyl-4-propoxy-3-pyridinecarboxamide 1-oxide,
2,6-diethyl-N-(2,6-diethylphenyl)-4-isobutoxy-3-pyridinecarboxamide 1-oxide,
4-allyloxy-2,6-diethyl-N-(2,6-diethylphenyl)-3-pyridinecarboxamide 1-oxide,
The compounds of the general formula (I) on the 1-oxide thereof according to the present invention may be in the form of addition salt with an acid, such as hydrochloric acid, sulfuric acid, phosphoric acid, methanesulphonic acid, p-toluenesulfonic acid or trifluoroacetic acid. Such addition salts are also included in the present invention.
The compounds of the general formula (I) may be prepared by conducting the following processes successively. (1) A compound of the general formula (IV) is prepared by the reaction of a compound of the general formula (VII) or (VII') with a compound of the general formula (VIII) (Reaction A), or by the reaction of a compound of the general formula (VII) or (VII') with a compound of the general formula (IX) or diketene (Reaction B). (2) And the compound of the general formula (IV) is converted to a compound of the general formula (II) by the reaction of the compound of general formula (IV) with ammonia (Reaction C) or a compound of the general formula (VI) with halogenating agent (Reaction D). (3) And the compound of the general formula (I) is obtained by the reaction of the compound of the general formula (II) with a compound of the general formula (III) (Reaction E). ##STR3##
In the above formulae, R.sup.6 is dialkylamino group such as dimethylamino, or 1-pyrrolidinyl and the like; m is an integer of from 0 to 6, R.sup.7 is alkyl group such as methyl, ethyl and the like; R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are as defined in the general formula (I).
The reaction A may be conducted in an inert solvent such as xylene, in the presence of a molecular sieve at 100.degree.-200.degree. C. ##STR4##
In the above formulae, R.sup.8 and R.sup.9 are hydrogen, alkyl or phenyl group; when R.sup.8 and R.sup.9 are alkyl groups, they may form cycloalkyl linkage; R.sup.2, R.sup.3, R.sup.6 and m are as defined before.
The reaction B is specific to a compound of the general formula (IV'), which is the specific one of the general formula (IV) wherein R.sup.4 is methyl and R.sup.5 is hydrogen.
A preferred compound of the general formula (IX) is 2,2,6-trimethyl-4H-1,3-dioxin-4-one.
The reaction B may be conducted in the presence of an inert solvent such as benzene, toluene or xylene.
The reaction temperature is preferably in the range from 100.degree. C. to 150.degree. C. when the compound of the general formula (IX) is used, and is preferably in the range from -20.degree. C. to 130.degree. C. when diketene is used. ##STR5##
In the formulae, R.sup.2 -R.sup.5 are as defined before.
The reaction C may be conducted in the presence of a solvent such as ethanol or water, at a low temperature such as in the range from room temperature to about 60.degree. C.
The amount of ammonia is equivalent to or more moles than one mole of the compound of the formula (IV) although it may be large excess. ##STR6##
In the formula, R.sup.2, R.sup.3 and R.sup.4 are as defined in the formula (I). The compound of the general formula (II) wherein R.sup.5 is halogen atom is obtained by the above reaction D. ##STR7##
In the above formula, Y is chlorine, bromine or iodine atom.
This reaction may be conducted by reacting 1,4-dihydro-4-oxo-3-pyridinecarboxamide compounds with a halogenated compound in the presence of a base such as potassium carbonate, sodium hydroxide or the like and also in the presence of an appropriate solvent such as N,N-dimethylformamide, dimethylsulfoxide or the like, preferably under heating.
The 1-oxide compound of this invention which is indicated by the general formula (I'), may be obtained by the reaction as follows: ##STR8##
This method is conducted by treating 4-(substituted-oxy)-3-pyridinecarboxamide compound with an oxidizer i.e., hydroperoxide such as hydrogen peroxide, tertiary butyl hydroperoxide or the like, or an organic peracid such as peracetic acid, perbenzoic acid, m-chloroperbenzoic acid or the like in the presence of an appropriate solvent.
This invention is further illustrated by examples hereinafter. The physical properties of the compounds in the examples are indicated in Table-1. The plant growth inhibitory activities of the compounds in the examples are indicated in Table-2.
EXAMPLE 1
4-Butoxy-N-(2,6-diethylphenyl)-2,6-dimethyl-3-pyridinecarboxamide
A mixture of 895 mg (3.0 m mol) of N-(2,6-diethylphenyl)-1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamide, 617 mg (4.5 m mol) of n-butyl bromide, 414 mg (3.0 m mol) of potassium carbonate and 15 ml of N,N-dimethylformamide was stirred for 2 hours at 90.degree. C.
About 50 ml of water was added to the reaction mixture and the mixture was cooled to room temperature to precipitate a solid. The obtained solid was crystallized from a mixture of ethyl acetate and hexane to obtain 870 mg of the title compound (Yield: 82%).
m.p.: 143.degree.-145.degree. C.
EXAMPLES 2-11
The following compounds were obtained from the corresponding 1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamides and the corresponding halogenated compounds in a similar way to the method of Example 1. When boiling point of the halogenated compound employed was lower than 90.degree. C., the reaction however was carried out at refluxing temperature. The halogenated compounds employed as the raw material were mentioned in Table-1.
4-ethoxy-2,6-dimethyl-N-phenyl-3-pyridinecarboxamide (Example 2),
4-allyloxy-2,6-dimethyl-N-phenyl-3-pyridinecarboxamide (Example 3),
4-benzyloxy-2,6-dimethyl-N-phenyl-3-pyridinecarboxamide (Example 4),
4-methoxycarbonylmethoxy-2,6-dimethyl-N-phenyl-3-pyridinecarboxamide (Example 5),
N-(2,6-diethylphenyl)-2,6-dimethyl-4-propoxy-3-pyridinecarboxamide (Example 6),
4-benzyloxy-N-(2,6-diethylphenyl)-2,6-diimethyl-3-pyridinecarboxamide (Example 7),
N-(2,6-diethylphenyl)-2,6-dimethyl-4-(2-phenylethyloxy)-3-pyridinecarboxamide (Example 8),
5-bromo-4-butoxy-N-(2,6-diethylphenyl)-2,6-dimethyl-3-pyridinecarboxamide (Example 9),
N-(2-chlorophenyl)-2,6-dimethyl-4-propoxy-3-pyridinecarboxamide (Example 10),
2,6-dimethyl-N-(2,3-dimethylphenyl)-4-propoxy-3-pyridinecarboxamide (Example 11),
EXAMPLE 12
2,6-Dimethyl-N-phenyl-4-propoxy-3-pyridinecarboxamide
A mixture of 2.42 g (10 m mol) of 1,4-dihydro-2,6-dimethyl-4-oxo-N-phenyl-3-pyridinecarboxamide, 1.84 g (15 m mol) of n-propyl bromide, 1.52 g (11 m mol) of potassium carbonate and 40 ml of N,N-dimethyl formamide was stirred for 7 hours in a bath at 90.degree. C.
About 100 ml of water was added to the reaction mixture. Precipitated crystals were filtered off and dried to obtain 2.14 g of the title compound (Yield: 75.3%)
m.p.: 129.degree.-131.degree. C.
EXAMPLES 13-50
The following compounds were obtained by a similar method to Example 12, from the corresponding 1,4-dihydro-4-oxo-3-pyridinecarboxamides and the corresponding halogenated compounds. The halogenated compounds used as the raw material were mentioned in Table-1.
4-butoxy-2,6-dimethyl-N-phenyl-3-pyridinecarboxamide (Example 13),
2,6-dimethyl-N-(2-methylphenyl)-4-propoxy-3-pyridinecarboxamide (Example 14),
4-ethoxy-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide (Example 15),
4-butoxy-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide (Example 16),
4-isobutoxy-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide (Example 17),
2,6-dimethyl-N-(2,3-dimethylphenyl)-4-pentyloxy-3-pyridinecarboxamide (Example 18),
4-isopentyloxy-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide (Example 19),
4-hexyloxy-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide (Example 20),
2,6-dimethyl-N-(2,3-dimethylphenyl)-4-octyloxy-3-pyridinecarboxamide (Example 21),
4-allyloxy-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide (Example 22),
2,6-dimethyl-N-(2,3-dimethylphenyl)-4-(2-propynyloxy)-3-pyridinecarboxamide (Example 23),
2,6-dimethyl-N-(2,3-dimethylphenyl)-4-(2-phenylethyloxy)-3-pyridinecarboxamide (Example 24),
4-cyclohexylmethyloxy-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide (Example 25),
2,6-dimethyl-N-(2,6-dimethylphenyl)-4-propoxy-3-pyridinecarboxamide (Example 26),
4-ethoxy-N-(2,6-diethylphenyl)-2,6-dimethyl-3-pyridinecarboxamide (Example 27),
N-(2,6-diethylphenyl)-4-isopropoxy-2,6-dimethyl-3-pyridinecarboxamide (Example 28),
N-(2,6-diethylphenyl)-4-isobutoxy-2,6-dimethyl-3-pyridinecarboxamide (Example 29),
N-(2,6-diethylphenyl)-2,6-dimethyl-4-pentyloxy-3-pyridinecarboxamide (Example 30),
4-ethoxycarbonylmethyloxy-N-(2,6-diethylphenyl)-2,6-dimethyl-3-pyridinecarboxamide (Example 31),
4-(1-ethoxycarbonylethyloxy)-N-(2,6-diethylphenyl)-2,6-dimethyl-3-pyridinecarboxamide (Example 32),
5-bromo-N-(2,6-diethylphenyl)-2,6-dimethyl-4-propoxy-3-pyridinecarboxamide (Example 33),
N-(2-methoxyphenyl)-2,6-dimethyl-4-propoxy-3-pyridinecarboxamide (Example 34),
2,6-dimethyl-N-(3-nitrophenyl)-4-propoxy-3-pyridinecarboxamide (Example 35),
4-(2-ethoxyethoxy)-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide (Example 36),
4-(2-chloroethoxy)-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide (Example 37),
N-(4-bromo-2,6-diethylphenyl)-2,6-dimethyl-4-propoxy-3-pyridinecarboxamide (Example 38),
6-methyl-N,2-diphenyl-4-propoxy-3-pyridinecarboxamide (Example 39),
6-methyl-N-(2,3-dimethylphenyl)-2-phenyl-4-propoxy-3-pyridinecarboxamide (Example 40),
N-(2,6-diethylphenyl)-6-methyl-2-phenyl-4-propoxy-3-pyridinecarboxamide (Example 41),
N-(4-bromo-2,6-diethylphenyl)-4-butoxy-2,6-dimethyl-3-pyridinecarboxamide (Example 42),
2-ethyl-N-(2,6-diethylphenyl)-6-methyl-4-propoxy-3-pyridinecarboxamide (Example 43),
5-bromo-N-(4-bromo-2,6-diethylphenyl)-2,6-dimethyl-4-propoxy-3-pyridinecarboxamide (Example 44),
N-(2,6-diethylphenyl)-2,5,6-trimethyl-4-propoxy-3-pyridinecarboxamide (Example 45),
4-butoxy-2,5,6-trimethyl-N-phenyl-3-pyridinecarboxamide (Example 46),
2,6-diethyl-N-(2,6-diethylphenyl)-4-propoxy-3-pyridinecarboxamide (Example 47),
N-(2,6-diethylphenyl)-2-methyl-6-phenyl-4-propoxy-3-pyridinecarboxamide (Example 48),
N-(2,6-diethylphenyl)-5,6,7,8-tetrahydro-2-methyl-4-propoxy-3-quinolinecarboxamide (Example 49),
6-butyl-N-(2,6-diethylphenyl)-2-methyl-4-propoxy-3-pyridinecarboxamide (Example 50),
EXAMPLE 51
2,6-Dimethyl-N-phenyl-4-propoxy-3-pyridinecarboxamide 1-oxide
A mixture of 2.42 (10 m mol) of 1,4-dihydro-2,6-dimethyl-4-oxo-N-phenyl-3-pyridinecarboxamide, 1.84 g (15 m mol) of n-propyl bromide, 1.52 g (11 m mol) of potassium carbonate and 40 ml of N,N-dimethylformamide was stirred for 7 hours at 90.degree. C. (bath temperature). About 100 ml of water was added to the reaction mixture. The mixture was cooled to room temperature to precipitate crystals. The crystals were filtered off, washed and dried under reduced pressure to obtain 2.14 g of 2,6-dimethyl-N-phenyl-4-propoxy-3-pyridinecarboxamide
Yield: 75.3%)
m.p.: 129.degree.-131.degree. C.
Then a mixture of 1.42 g (5 m mol) of 2,6-dimethyl-N-phenyl-4-propoxy-3-pyridinecarboxamide obtained thus, 2.16 g (10 m mol) of a commercially available m-chloroperbenzoic acid (80% purity) and 40 ml of chloroform was stirred for 8 hours at room temperature. The reaction mixture was discharged to a separation funnel and after the addition of the 10% aqueous sodium hydrogen sulfite solution, was shaken. The separated oil phase was washed with aqueous saturated sodium hydrogen carbonate solution and then with aqueous saturated sodium chloride solution. It was then dehydrated over anhydrous magnesium sulfate and filtered. After the filtrate was concentrated, the residue was crystallized from a mixture of ethyl acetate and hexane to obtain 1.37 g of the title compound
(Yield: 91.2%).
m.p.: 185.degree.-186.degree. C.
EXAMPLES 52-90
The following compounds were obtained from the corresponding 4-substitutedoxy-3-pyridinecarboxamide compounds, which were obtained by the reaction of the corresponding 1,4-dihydro-4-oxo-3-pyridinecarboxamide compounds with halogenated compounds, in a similar method to Example 51.
4-butoxy-2,6-dimethyl-N-phenyl-3-pyridinecarboxamide 1-oxide (Example 52),
2,6-dimethyl-N-(2-methylphenyl)-4-propoxy-3-pyridinecarboxamide 1-oxide (Example 53),
2,6-dimethyl-N-(2,6-dimethylphenyl)-4-propoxy-3-pyridinecarboxamide 1-oxide (Example 54),
4-butoxy-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide 1-oxide (Example 55),
4-isobutoxy-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide 1-oxide (Example 56),
2,6-dimethyl-N-(2,3-dimethylphenyl)-4-pentyloxy-3-pyridinecarboxamide 1-oxide (Example 57),
4-isopentyloxy-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide 1-oxide (Example 58),
4-hexyloxy-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide 1-oxide (Example 59),
2,6-dimethyl-N-(2,3-dimethylphenyl)-4-octyloxy-3-pyridinecarboxamide 1-oxide (Example 60),
4-(2-ethoxyethoxy)-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide 1-oxide (Example 61), 4-allyloxy-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide 1-oxide (Example 62),
2,6-dimethyl-N-(2,4-dimethylphenyl)-4-propoxy-3-pyridinecarboxamide 1-oxide (Example 63),
4-ethoxy-N-(2,6-diethylphenyl)-2,6-dimethyl-3-pyridinecarboxamide 1-oxide (Example 64),
N-(2,6-diethylphenyl)-2,6-dimethyl-4-propoxy-3-pyridinecarboxamide 1-oxide (Example 65),
N-(2,6-diethylphenyl)-4-isopropoxy-2,6-dimethyl-3-pyridinecarboxamide 1-oxide (Example 66),
4-butoxy-N-(2,6-diethylphenyl)-2,6-dimethyl-3-pyridinecarboxamide 1-oxide (Example 67),
N-(2,6-diethylphenyl)-4-isobutoxy-2,6-dimethyl-3-pyridinecarboxamide 1-oxide (Example 68),
N-(2,6-diethylphenyl)-2,6-dimethyl-4-pentyloxy-3-pyridinecarboxamide 1-oxide (Example 69),
4-benzyloxy-N-(2,6-diethylphenyl)-2,6-dimethyl-3-pyridinecarboxamide 1-oxide (Example 70),
4-ethoxycarbonylmethoxy-N-(2,6-diethylphenyl)-2,6-dimethyl-3-pyridinecarboxamide 1-oxide (Example 71),
4-(1-ethoxycarbonylethoxy)-N-(2,6-dimethylphenyl)-2,6-dimethyl-3-pyridinecarboxamide 1-oxide (Example 72),
N-(2-methoxyphenyl)-2,6-dimethyl-4-propoxy-3-pyridinecarboxamide 1-oxide (Example 73),
2,6-dimethyl-N-(3-nitrophenyl)-4-propoxy-3-pyridinecarboxamide 1-oxide (Example 74),
6-methyl-N,2-diphenyl-4-propoxy-3-pyridinecarboxamide 1-oxide (Example 75),
5-bromo-N-(2,6-diethylphenyl)-2,6-dimethyl-4-propoxy-3-pyridinecarboxamide 1-oxide (Example 76),
6-methyl-N-(2,3-dimethylphenyl)-2-phenyl-4-propoxy-3-pyridinecarboxamide 1-oxide (Example 77),
N-(2,6-diethylphenyl)-6-methyl-2-phenyl-4-propoxy-3-pyridinecarboxamide 1-oxide (Example 78),
4-cyclohexylmethoxy-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide 1-oxide (Example 79),
4-(2-chloroethoxy)-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide 1-oxide (Example 80),
N-(4-bromo-2,6-diethylphenyl)-2,6-dimethyl-4-propoxy-3-pyridinecarboxamide 1-oxide (Example 81),
N-(2,6-diethylphenyl)-2,6-dimethyl-4-(2-phenylethyloxy)-3-pyridinecarboxamide 1-oxide (Example 82),
5-bromo-N-(4-bromo-2,6-diethylphenyl)-2,6-dimethyl-4-propoxy-3-pyridinecarboxamide 1-oxide (Example 83),
2-ethyl-N-(2,6-diethylphenyl)-6-methyl-4-propoxy-3-pyridinecarboxamide 1-oxide (Example 84),
N-(2,6-diethylphenyl)-2,5,6-trimethyl-4-propoxy-3-pyridinecarboxamide 1-oxide (Example 85),
2,6-diethyl-N-(2,6-diethylphenyl)-4-propoxy-3-pyridinecarboxamide 1-oxide (Example 86),
4-butoxy-2,5,6-trimethyl-N-phenyl-3-pyridinecarboxamide 1-oxide (Example 87),
6-butyl-N-(2,6-diethylphenyl)-2-methyl-4-propoxy-3-pyridinecarboxamide 1-oxide (Example 88),
N-(2,6-diethylphenyl)-5,6,7,8-tetrahydro-2-methyl-4-propoxy-3-quinolinecarboxamide 1-oxide (Example 89),
N-(2,6-diethylphenyl)-4-isobutoxy-5,6-dimethyl-2-propyl-3-pyridinecarboxamide 1-oxide (Example 90),
REFERENCE EXAMPLE
A carrier was prepared by mixing 50 parts (by weight) of talc, 25 parts of bentonite, 2 parts of "Solpole-9047" (Toho Chemical Co., Ltd, Japan) and 3 parts of "Solpole-5039" (Toho Chemical Co., Ltd, Japan). 50 parts of a test compound and 200 parts of the carrier were mixed to obtain 20% wettable powder, followed by dispersing the powder in distilled water to make a dispersion of the definite concentrations.
Seeds of Oryza sativa L., Echinochloa crus-galli L., and Raphanus sativus L., were germinated in a laboratory dish, to which the dispersion was added. After breeding for 7 days in a thermostatic box kept at 25.degree. C. under illumination of fluorescent tubes, growth of plant was observed. In the column of "Evaluation" of Table 2, the designation 1 denotes no influence, 2 denotes 25% growth inhibition, 3 denotes 50% growth inhibition, 4 denotes 75% growth inhibition and 5 denotes 100% growth inhibition.
TABLE 1__________________________________________________________________________Example IR(KBr)No. R' Y NMR (CDCl.sub.3) .delta.-value cm.sup.-1 m.p. (.degree.C.)__________________________________________________________________________ 1 n-butyl 0.60-2.20(m, 7H), 1.23(t, 6H), 2.50(s, 3H), 2.63(s, 1643 143-145 bromide 2.75(q, 4H), 4.07(t, 2H), 6.56(s, 1H), 6.80-7.40(m, 4H) 2 ethyl iodide 1.41(t, 3H), 2.48(s, 3H), 2.56(s, 3H), 4.10(q, 1663 1335-1355 6.52(s, 1H), 6.65-7.77(m, 5H), 7.91(br, 1H) 3 allyl bromide 2.32(s, 3H), 2.49(s, 3H), 4.54(d, 2H), 5.04-5.54(m, 1647 foaming 5.59-6.29(m, 1H), 6.46(s, 1H), 6.89-7.79(m, 5H), 8.42(br, 1H) 4 benzyl 2.46(s, 3H), 2.57(s, 3H), 5.10(s, 2H), 6.60(s, 1642 172-174 bromide 6.75-7.80(m, 10H), 7.97(br, 1H) 5 methyl .alpha.- 2.46(s, 3H), 2.58(s, 3H), 3.77(s, 3H), 4.73(s, 1672 129-132 bromoacetate 6.43(s, 1H), 6.80-7.80(m, 5H), 8.58(br, 1H) 1748 6 n-propyl 1.01(t, 3H), 1.21(t, 6H), 1.40-2.20(m, 2H), 2.48(s, 1637 154-157 bromide 2.60(s, 3H), 2.72(q, 4H), 4.00(t, 2H), 6.51(s, 1H), 6.80-7.30(m, 4H) 7 benzyl 1.06(t, 6H), 2.50(s, 3H), 2.57(q, 4H), 2.66(s, 1633 179-181 bromide 5.13(s, 2H), 6.62(s, 1H), 6.80-7.50(m, 9H) 8 phenetyl 1.20(t, 6H), 2.49(s, 3H), 2.63(s, 3H), 2.67(q, 4H), 1642 166-169 bromide (t, 2H), 4.31(t, 2H), 6.57(s, 1H), 6.80-7.50(m, 9H) 9 n-butyl 0.60-2.30(m, 7H), 1.23(t, 6H), 2.62(s, 3H), 2.65(s, 1640 184-1855 bromide 2.74(q, 4H), 4.06(t, 2H), 6.80-7.30(m, 4H)10 n-propyl 0.97(t, 3H), 1.40-2.20(m, 2H), 2.48(s, 3H), 2.58(s, 1677 111.5-113.5 bromide 3.98(t, 2H), 6.53(s, 1H), 6.70-8.70(m, 5H)11 n-propyl 1.01(t, 3H), 1.40-2.20(m, 2H), 2.21(s, 3H), 2.30(s, 3H), 1673 163-166 bromide (s, 3H), 2.59(s, 3H), 4.00(t, 2H), 6.54(s, 1H), 6.97-7.80(m, 4H)12 n-propyl 0.94(t, 3H), 1.73(six, 2H), 2.41(s, 3H), 2.46(s, 1670 129-131 bromide 3.88(t, 2H), 6.38(s, 1H), 6.80-7.85(m, 5H), 8.48(s, 1H)13 n-butyl 0.60-2.30(m, 7H), 2.45(s, 3H), 2.51(s, 3H), 1667 110-112 bromide 3.97(t, 2H), 6.45(s, 1H), 6.85-8.00(m, 5H), 8.33(s, 1H)14 n-propyl 1.00(t, 3H), 1.82(six, 2H), 2.28(s, 3H), 2.48(s, 1638 137-137.5 bromide 2.57(s, 3H), 3.99(t, 2H), 6.53(s, 1H), 6.85-8.00(m, 4H), 7.45(s, 1H)15 ethyl 1.42(t, 3H), 2.20(s, 3H), 2.28(s, 3H), 2.47(s, 1662 184-187 iodide 2.57(s, 3H), 4.08(q, 2H), 6.47(s, 1H), 6.80-7.60(m, 3H), 7.33(s, 1H)16 n-butyl 0.60-2.10(m, 7H), 2.19(s, 3H), 2.28(s, 3H), 1645 132-134 bromide 2.48(s, 3H), 2.57(s, 3H), 4.00(t, 2H), 6.50(s, 1H), 6.80-7.60(m, 4H)17 isobutyl 1.00(d, 6H), 1.70-2.40(m, 1H), 2.20(s, 3H), 1650 148-149 bromide 2.30(s, 3H), 2.48(s, 3H), 2.58(s, 3H), 3.79(d, 2H), 6.50(s, 1H), 6.85-7.60(m, 4H)18 n-amyl 0.60-2.15(m, 9H), 2.20(s, 3H), 2.29(s, 3H), 1645 133.5-135 bromide 2.47(s, 3H), 2.57(s, 3H), 4.00(t, 2H), 6.50(s, 1H), 6.80-7.70(m, 4H)19 isoamyl 0.92(d, 6H), 1.30-2.10(m, 3H), 2.17(s, 3H), 1640 132-134 bromide 2.27(s, 3H), 2.44(s, 3H), 2.52(s, 3H), 4.00(t, 2H), 6.48(s, 1H), 6.80-7.55(m, 3H), 7.70(s, 1H)20 n-hexyl 0.60-2.10(m, 11H), 2.18(s, 3H), 2.28(s, 3H), 1648, 125-127 bromide 2.46(s, 3H), 2.55(s, 3H), 3.99(t, 2H), 6.49(s, 1670 6.95-7.70(m, 3H), 7.50(s, 1H)21 n-octyl 0.60-2.10(m, 15H), 2.16(s, 3H), 2.26(s, 3H), 1645 139-141 bromide 2.43(s, 3H), 2.50(s, 3H), 3.95(t, 2H), 6.47(s, 1H), 6.70-7.60(m, 3H), 7.87(s, 1H)22 allyl 2.17(s, 3H), 2.27(s, 3H), 2.47(s, 3H), 2.58(s, 1640, 148-151 bromide 4.57(d, 2H), 5.05-5.60(m, 2H), 5.60-6.40(m, 1653 6.50(s, 1H), 6.80-7.70(m, 4H)23 propargyl 2.23(s, 3H), 2.31(s, 3H), 2.53(s, 3H), 2.57(t, 1643 180.5-182 bromide 2.62(s, 3H), 4.75(d, 2H), 6.67(s, 1H), 6.90-7.90(m, 4H)24 .beta.-phenetyl 2.09(s, 3H), 2.28(s, 3H), 2.45(s, 3H), 2.54(s, 1640 152-157 bromide 3.05(t, 2H), 4.22(t, 2H), 6.49(s, 1H), 6.60-7.60(m, 9H)25 cyclohexyl- 0.50-2.10(m, 11H), 2.18(s, 3H), 2.27(s, 3H), 1648 164-167 methyl 2.43(s, 3H), 2.53(s, 3H), 3.76(d, 2H), 6.46(s, 1H), bromide 6.70-7.60(m, 3H), 7.80(s, 1H)26 n-propyl 1.00(t, 3H), 1.83(six, 2H), 2.33(s, 6H), 1640 166-169 bromide 2.48(s, 3H), 2.60(s, 3H), 4.00(t, 2H), 6.55(s, 1H), 7.08(s, 3H), 7.24(s, 1H)27 ethyl 1.21(t, 6H), 1.43(t, 3H), 2.47(s, 3H), 2.59(s, 1640 180-183 iodide 2.73(q, 4H), 4.11(q, 2H), 6.54(s, 1H), 6.90-7.50(m, 4H)28 isopropyl 1.20(t, 6H), 1.36(d, 6H), 2.44(s, 3H), 2.56(s, 1638 171-175.5 iodide 2.70(q, 4H), 4.63(sep, 1H), 6.49(s, 1H), 6.90-7.40(m, 3H), 7.17(s, 1H)29 isobutyl 0.99(d, 6H), 1.20(t, 6H), 1.70-2.50(m, 1H), 1635 164- 165 bromide 2.46(s, 3H), 2.57(s, 3H), 2.71(q, 4H), 3.79(d, 2H), 6.52(s, 1H), 6.90-7.50(m, 3H), 7.26(s, 1H)30 n-amyl 0.60-2.20(m, 9H), 1.22(t, 6H), 2.48(s, 3H), 1635 143-145 bromide 2.60(s, 3H), 4.04(t, 2H), 6.55(s, 1H), 6.90-7.50(m, 4H)31 ethyl 1.20(t, 6H), 1.23(t, 3H), 2.47(s, 3H), 2.65(s, 1640, 157-159 bromo- 2.71(q, 4H), 4.18(q, 2H), 4.73(s, 2H), 6.47(s, 1745 acetate 7.00-7.30(m, 3H), 7.96(s, 1H) 177032 ethyl .alpha.- 1.23(t, 9H), 1.66(d, 3H), 2.46(s, 3H), 2.64(s, 1638, 156.5-159 bromo- 2.75(q, 4H), 4.17(q, 2H), 4.98(q, 1H), 6.45(s, 1732 propionate 7.00-7.30(m, 3H), 8.01(s, 1H)33 n-propyl 0.97(t, 3H), 1.21(t, 6H), 1.79(six, 2H), 1640 172-177 bromide 2.57(s, 3H), 2.63(s, 3H), 2.70(q, 4H), 4.00(t, 2H), 7.00-7.30(m, 3H), 7.35(s, 1H)34 n-propyl 0.94(t, 3H), 1.76(six, 2H), 2.47(s, 3H), 2.57(s, 3H), 3.78(s, 3H), 1670 120-122 bromide 3.97(t, 2H), 6.55(s, 1H), 6.60-8.70(m, 4H), 8.23(s, 1H)35 n-propyl 0.96(t, 3H), 1.78(six, 2H), 2.43(s, 3H), 2.46(s, 3H), 3.96(t, 2H), 1657 152-153 bromide 6.46(s, 1H), 7.25-8.65(m, 4H), 9.04(s, 1H)36 2-bromoethyl 1.05(t, 3H), 2.17(s, 3H), 2.26(s, 3H), 2.43(s, 3H), 2.52(s, 3H), 1645 126.5-128 ethyl ether 3.43(q, 2H), 3.50-3.90(m, 2H), 3.90-4.30(m, 2H), 6.47(s, 1H), 6.80-7.50(m, 3H), 8.07(s, 1H)37 1-bromo-2- 2.21(s, 3H), 2.27(s, 3H), 2.48(s, 3H), 2.59(s, 3H), 3.77(t, 2H), 1645 123-125 chloroethane 4.27(t, 2H), 6.49(s, 1H), 6.80-7.60(m, 4H)38 n-propyl 1.00(t, 3H), 1.20(t, 6H), 1.82(six, 2H), 2.47(s, 3H), 2.59(s, 3H), 1643 202-205.5 bromide 2.67(q, 4H), 3.99(t, 2H), 6.50(s, 1H), 7.00(br, 1H), 7.18(s, 2H)39 n-propyl 0.97(t, 3H), 1.76(six, 2H), 2.58(s, 3H), 3.97(t, 2H), 6.62(s, 1H), 1645 143.5-146 bromide 6.80-8.10(m, 11H)40 n-propyl 0.99(t, 3H), 1.20-2.30(m, 2H), 1.80(s, 3H), 2.17(s, 1645 165-169 bromide 2.53(s, 3H), 3.95(t, 2H), 6.57(s, 1H), 6.70-7.85(m, 9H)41 n-propyl 0.95(t, 6H), 1.01(t, 3H), 1.81(six, 2H), 2.16(q, 4H), 2.56(s, 3H), 1637 214-216 bromide 3.97(t, 2H), 6.64(s, 1H), 6.80-7.90(m, 9H)42 n-butyl 0.60-2.20(m, 7H), 1.23(t, 6H), 2.52(s, 3H), 2.63(s, 3H), 2.74(q, 4H), 1647 bromide 4.10(t, 2H), 6.58(s, 1H), 7.02(br, 1H), 7.10-7.35(m, 2H)43 n-propyl 1.00(t, 3H), 1.23(t, 6H), 1.81(t, 3H), 1.79(six, 2H), 2.50(s, 3H), 1647 bromide 2.75(q, 4H), 2.89(q, 2H), 4.00(t, 2H), 6.51(s, 1H), 6.90-7.25(m, 4H)44 n-propyl 1645 bromide45 n-propyl 0.96(t, 3H), 1.23(t, 6H), 1.79(six, 2H), 2.19(s, 1H), 2.47(s, 3H), 1647 150-152 bromide 2.61(s, 3H), 2.74(q, 4H), 3.85(t, 2H), 6.90-7.30(m, 4H)46 n-butyl 0.60-2.25(m, 7H), 2.10(s, 3H), 2.41(s, 3H), 2.47(s, 3H), 3.88(t, 2H) 1673 102-106 bromide 6.80-7.90(m, 5H), 8.33(br, 1H)47 n-propyl 1.00(t, 3H), 1.23(t, 6H), 1.34(t, 6H), 1.84(six, 2H), 2.76(q, 6H), 1640 210-213 bromide 2.92(q, 2H), 4.01(t, 2H), 6.52(s, 1H), 6.90-7.40(m, 4H)48 n-propyl 1.01(t, 3H), 1.21(t, 6H), 1.86(six, 2H), 2.68(s, 3H), 2.73(q, 4H), 1650 172-176 bromide 4.05(t, 2H), 6.80-8.15(m, 10H)49 n-propyl 0.70-1.45(m, 9H), 1.45-2.20(m, 6H), 2.20-3.10(m, 11H), 3.87(t, 2H) 1665 bromide 6.90-7.30(m, 4H) (neat)50 n-propyl 0.60-2.35(m, 12H), 1.21(t, 6H), 2.40-3.20(m, 6H), 2.60(s, 3H), 1643 100-103 bromide 3.99(t, 2H), 6.50(s, 1H), 6.90-7.40(m, 4H)__________________________________________________________________________Example IR(KBr) m.p.No. N M R (C D C l.sub.3 *) .delta.-value .nu.c = o (cm.sup.-1) ( .degree.C.)__________________________________________________________________________51 0.98(t, 3H), 1.77(six, 2H), 2.38(s, 6H), 1660 185-186 3.93(t, 2H), 6.46(s, 1H), 6.90-8.10(m, 5H), 11.10(s, 1H)52 0.60-2.20(m, 7H), 2.86(s, 6H), 3.95(t, 2H), 6.43(s, 1662 201-201.5 6.85-8.00(m, 5H), 10, 84(s, 1H)53 1.04(t, 3H), 1.78(six, 2H), 2.42(s, 6H), 2.51(s, 1660 245-246 3.97(t, 2H), 6.56(s, 1H), 7.00-7.80(m, 4H), 9.60(s, 1H)54 1663 264-265.555 0.60-2.20(m, 7H), 2.29(s, 3H), 2.33(s, 3H), 2.47(s, 1660 253-255 2.56(s, 3H), 4.06(t, 2H), 6.75(s, 1H), 6.95-7.60(m, 3H), 9.85(s, 1H)56 1.03(d, 6H), 1.70-2.60(m, 1H), 2.30(s, 6H), 2.34(s, 1667 258-259.5 2.48(s, 3H), 3.73(d, 2H), 6.46(s, 1H), 6.85-7.50(m, 3H), 9.86(s, 1H)57 0.60-2.20(m, 9H), 2.31(s, 6H), 2.39(s, 3H), 2.51(s, 1660 211-213 4.03(t, 2H), 6.57(s, 1H), 7.00-7.60(m, 3H), 9.69(s, 1H)58 1662 224-22659 0.60-2.15(m, 11H), 2.30(s, 6H), 2.36(s, 3H), 2.48(s, 3H), 3.97(t, 2H), 1665 230-231 6.50(s, 1H), 6.95-7.50(m, 3H), 9.89(s, 1H)60 0.60-2.15(m, 15H), 2.30(s, 6H), 2.33(s, 3H), 2.47(s, 1660 199-201.5 3.93(t, 2H), 6.45(s, 1H), 6.90-7.50(m, 3H), 9.99(s, 1H)61 1.15(t, 3H), 2.30(s, 6H), 2.40(s, 3H), 2.53(s, 3H), 3.52(q, 2H), 3.60- 1660 187.5-189 3.90(m, 2H), 4.00-4.35(m, 2H), 6.60(s, 1H), 6.90-7.50(m, 3H), 9.68(s, 1H)62 2.25(s, 3H), 2.30(s, 3H), 2.45(s, 3H), 2.53(s, 3H), 1662 228.5-231 (d, 2H), 5.00-6.40(m, 3H), 6.61(s, 1H), 6.90-7.60(m, 3H), 8.60(s, 1H)63 1.03(t, 3H), 1.86(six, 2H), 2.43(s, 9H), 2.60(s, 1648 2375-238.5 3.97(t, 2H), 6.54(s, 1H), 7.09(s, 3H), 9.50(s, 1H)64 1.26(t, 6H), 1.44(t, 3H), 2.34(s, 3H), 2.56(s, 3H), 1645 218-218.5 (q, 4H), 4.03(q, 2H), 6.48(s, 1H), 6.90-7.40(m, 3H), 9.72(s, 1H)65 1.03(t, 3H), 1.28(t, 6H), 186(six, 2H), 2.37(s, 3H), 2.59(s, 1645 233-234 2.82(q, 4H), 3.95(t, 2H), 6.49(s, 1H), 6.90-7.30(m, 3H), 9.58(s, 1H)66 1.28(t, 6H), 1.33(d, 6H), 2.34(s, 3H), 2.54(s, 3H), 1645 111-115 (q, 4H), 4.51(sep, 1H), 6.49(s, 1H), 7.10(s, 3H), 9.90(s, 1H)67 0.60-2.20(m, 7H), 1.27(t, 6H), 2.36(s, 3H), 2.57(s, 3H), 2.81(q, 4H), 1645 215-216 4.00(t, 2H), 6.52(s, 1H), 6.90-7.40(m, 3H), 9.75(s, 1H)68 1.03(d, 5H), 1.29(t, 6H), 1.70-2.60(m, 1H), 2.36(s, 3H), 2.59(s, 3H), 1670 158-159.5 2.83(q, 4H), 3.76(d, 2H), 6.47(s, 1H), 6.90-7.40(m, 3H), 9.83(s, 1H)69 0.60-2.20(m, 9H), 1.28(t, 6H), 2.34(s, 3H), 2.57(s, 1662 182-184.5 2.81(q, 4H), 3.97(t, 2H), 6.47(s, 1H), 7.00-7.30(m, 3H), 9.78(s, 1H)70 1.10(t, 6H), 2.44(s, 3H), 2.64(s, 3H), 2.66(q, 4H), 5.14(s, 1652 199-201 6.72(s, 1H), 6.90-7.80(m, 8H), 9.20(s, 1H)71 1.23(t, 6H), 1.26(t, 3H), 2.44(s, 3H), 2.62(s, 3H), 2.74(q, 4H), 4.20 1645 204.5-207 (q, 2H), 4.72(s, 2H), 6.64(s, 1H), 7.00-7.40(m, 3H), 8.87(s, 176772 1.25(t, 9H), 1.64(d, 3H), 2.44(s, 3H), 2.62(s, 3H), 1643(q, 165-167. 4H), 4.19(q, 2H), 4.89(q, 1H), 6.63(s, 1H), 7.03-7.40(m, 3H), 9.13(s, 1H) 177273 0.96(t, 3H), 1.77(six, 2H), 2.50(s, 3H), 2.58(s, 3H), 3.81(s, 1667 195-197 3.97(t, 2H), 6.68(s, 1H), 6.70-8.60(m, 4H), 8.44(s, 1H)74 0.98(t, 3H), 1.80(six, 2H), 2.40(s, 6H), 3.98(t, 1672 217.5-219 6.57(s, 1H), 7.30-9.00(m, 4H), 11.73(s, 1H)75 0.95(t, 3H), 1.75(six, 2H), 2.43(s, 3H), 3.93(t, 1650 191-195 6.71(s, 1H), 6.80-8.00(m, 10H), 8.49(s, 1H)76 1.00(t, 3H), 1.32(t, 6H), 1.84(six, 2H), 2.55(s, 3H), 1675 148-152 (s, 3H), 2.85(q, 4H), 4.01(t, 2H), 7.16(s, 3H), 9.88(s, 1H)77 0.97(t, 3H), 1.40-2.20(m, 2H), 1.70(s, 3H), 2.13(s, 1645 226-227 2.37(s, 3H), 3.87(t, 2H), 6.25-7.80(m, 9H), 8.03(s, 1H)78 0.94(t, 6H), 1.01(t, 3H), 1.80(six, 6H), 2.44(s, 1642 240-242 3.96(t, 2H), 6.60-8.00(m, 10H)79 0.80-2.20(m, 11H), 2.22(s, 3H), 2.28(s, 3H), 2.55(s, 1662 250-254 3.92(d, 2H), 4.68(s, 1H), 6.90-7.30(m, 4H)80 1650 187.5-191 166081 1.01(t, 3H), 1.24(t, 6H), 1.83(six, 2H), 2.30(s, 3H), 2.50(s, 1645 265-268 2.75(q, 4H), 3.92(t, 2H), 6.43(s, 1H), 7.18(s, 2H), 9.89(s, 1H)82 1645 202-20383 1687 228.5-23084 1.03(t, 3H), 1.23(t, 3H), 1.29(t, 6H), 1.87(six, 2H), 2.40(s, 1665 178-181 2.84(q, 4H), 3.10(q, 2H), 3.94(t, 2H), 6.48(s, 1H), 7.00-7.40(m, 3H) 9.50(s, 1H)85 0.97(t, 3H), 1.33(t, 6H), 1.79(six, 2H), 2.18(s, 3H), 2.35(s, 1680 175-177 2.56(s, 3H), 2.88(q, 4H), 3.85(t, 2H), 7.00-7.30(m, 3H), 10.10(s, 1H)86 1.03(t, 3H), 1.21(t, 6H), 1.28(t, 6H), 1.86(six, 2H), 2.79(q, 1663 138-140 2.82(q, 4H), 3.08(q, 2H), 3.92(t, 2H), 6.36(s, 1H), 7.00-7.20(m, 3H) 9.47(s, 1H)87 0.60-2.25(m, 7H), 2.12(s, 3H), 2.32(s, 3H), 2.35(s, 3H), 4.00(t, 2H) 1677 188-190 6.80- 8.00(m, 5H), 11.36(br, 1H)88 0.60-2.20(m, 12H), 1.79(t, 6H), 2.40-3.20(m, 6H), 2.58(s, 1673 3.94(t, 2H), 6.41(s, 1H), 7.00-7.25(m, 3H), 9.66(s, 1H)89 0.98(t, 3H), 1.30(t, 6H), 1.40-2.15(m, 6H), 2.20-3.10(m, 1673 193-196 2.59(s, 3H), 2.83(q, 4H), 3.91(t, 2H), 6.90-7.25(m, 3H), 9.68(s, 1H)90 0.95(t, 3H), 0.97(d, 6H), 1.30-2.50(m, 3H), 1.33(t, 6H), 2.18(s, 3H), 1673 210-214 2.37(s, 3H), 2.88(q, 4H), 3.30(t, 2H), 3.63(d, 2H), 7.13(s, 3H), 9.73(s, 1H)__________________________________________________________________________ *Example No. 55: CDC1.sub.3 --DMSO--d.sub.6 Example No. 79: CD.sub.3 OD
______________________________________ concentra-Example tion PlantNo. (ppm) X Y Z______________________________________ 1 20 4 4 4 100 5 5 4 2 20 1 3 3 100 4 4 4 3 20 1 4 4 100 4 4 5 4 20 1 2 1 100 2 2 1 5 20 1 1 1 100 2 2 1 6 20 4 4 4 100 4 5 4 7 20 3 3 4 100 3 4 4 8 20 1 1 2 100 1 2 2 9 20 1 4 2 100 1 4 210 20 4 5 4 100 5 5 411 20 4 5 4 100 4 5 412 20 3 4 4 100 4 5 413 20 2 4 4 100 5 5 414 20 4 4 4 100 4 4 415 20 2 4 4 100 4 4 416 20 4 5 4 100 4 5 417 20 4 5 4 100 4 5 418 20 5 5 5 100 5 5 519 20 5 5 4 100 5 5 520 20 4 5 4 100 5 5 421 20 1 3 1 100 2 4 122 20 4 5 4 100 4 5 523 20 1 4 4 100 1 4 424 20 2 2 1 100 3 3 425 20 3 2 4 100 3 4 526 20 4 4 4 100 4 4 427 20 4 5 4 100 4 5 428 20 1 4 4 100 2 5 429 20 4 5 5 100 5 5 530 20 4 4 4 100 5 5 431 20 1 1 4 100 4 4 532 20 1 2 3 100 4 5 433 20 4 5 3 100 4 5 434 20 2 5 5 100 5 5 535 20 3 5 4 100 5 5 536 20 2 3 4 100 4 5 537 20 5 5 5 100 5 5 538 20 -- -- -- 100 -- -- --39 20 4 5 5 100 5 5 540 20 5 5 5 100 5 5 541 20 5 5 5 100 5 5 542 20 4 5 5 100 4 5 543 20 4 5 4 100 5 5 444 20 -- -- -- 100 -- -- --45 20 4 5 5 100 4 5 546 20 1 4 3 100 4 5 547 20 5 5 5 100 5 5 548 20 1 1 4 100 2 1 449 20 5 5 4 100 5 5 450 20 3 5 4 100 3 5 451 20 1 3 4 100 4 4 452 20 1 2 4 100 3 4 453 20 1 4 4 100 4 4 454 20 4 4 5 100 5 5 555 20 3 4 4 100 4 5 456 20 4 5 4 100 5 5 457 20 4 5 4 100 5 5 458 20 3 4 5 100 4 4 559 20 1 3 4 100 1 3 460 20 1 1 1 100 1 1 161 20 1 1 4 100 4 4 462 20 4 5 5 100 5 5 563 20 1 4 4 100 4 4 464 20 4 4 4 100 5 5 465 20 4 4 4 100 4 5 466 20 5 5 5 100 5 5 567 20 4 4 4 100 5 5 568 20 4 4 4 100 5 5 469 20 2 4 4 100 4 4 470 20 1 1 4 100 3 4 471 20 1 1 3 100 1 1 572 20 1 3 1 100 1 3 573 20 2 4 4 100 3 4 574 20 2 5 5 100 5 5 575 20 4 5 5 100 4 5 576 20 5 5 5 100 5 5 577 20 4 4 5 100 4 5 578 20 4 5 4 100 5 5 479 20 2 1 4 100 3 3 480 20 4 3 5 100 4 4 581 20 4 5 5 100 5 5 582 20 -- -- -- 100 -- -- --83 20 5 5 5 100 5 5 584 20 2 5 5 100 5 5 585 20 4 4 5 100 5 5 586 20 5 5 5 100 5 5 587 20 1 1 3 100 1 3 488 20 1 4 5 100 4 5 589 20 1 3 5 100 4 4 590 20 5 5 5 100 5 5 5______________________________________ X: Ortyza sativa L. Y: Echinochloa crusgalli L. A: Raphanus sativus L.
Claims
- 1. A compound of the formula: ##STR9## wherein R.sup.1 is C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl, aralkyl selected from the group consisting of benzyl, 2-phenylethyl, 3-phenylpropyl and 4-phenylbutyl, haloalkyl, C.sub.1 -C.sub.6 alkoxy-C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkylthio-C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 alkoxycarbonyl-C.sub.1 -C.sub.6 alkyl;
- R.sup.2 is unsubstituted or substituted phenyl or naphthyl, wherein the substituents are selected from the group consisting of halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkoxycarbonyl, trifluoromethyl, cyano or nitro;
- R.sub.3 and R.sub.4 are selected from the group consisting of C.sub.1 -C.sub.6 alkyl, aralkyl selected from the group consisting of benzyl, 2-phenylethyl, 3-phenylpropyl and 4-phenylbutyl, haloalkyl, C.sub.3 -C.sub.6 cycloalkyl, unsubstituted phenyl or naphthyl, and substituted phenyl or naphthyl, wherein the substituents are selected form the group consisting of halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, trifluoromethyl, cyano or nitro;
- R.sup.5 is hydrogen, halogen, C.sub.1 -C.sub.6 alkyl, or unsubstituted or substituted phenyl or aralkyl selected from the group consisting of benzyl, 2-phenylethyl, 3-phenylpropyl and 4-phenylbutyl, wherein the substituents are selected from the group consisting of halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, trifluoromethyl, cyano or nitro;
- R.sup.4 and R.sup.5 or a 1-oxide or an acid addition salt thereof.
- 2. A compound of claim 1 in which R.sup.2 is 2,6-diethylphenyl group.
- 3. A compound of claim 1 in which R.sup.2 is 2,3-dimethylphenyl group.
- 4. A compound of claim 1 which is 2,6-dimethyl-N-(2,3-dimethylphenyl)-4-propoxy-3-pyridinecarboxamide,
- 4-butoxy-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide,
- 4-isobutoxy-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide,
- 2,6-dimethyl-N-(2,3-dimethylphenyl)-4-pentyloxy-3-pyridinecarboxamide,
- 4-isopentyloxy-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide,
- 4-allyloxy-2,6-dimethyl-N-(2,3-dimethylphenyl)-3-pyridinecarboxamide,
- N-(2,6-diethylphenyl)-2,6-dimethyl-4-propoxy-3-pyridinecarboxamide,
- N-(2,6-diethylphenyl)-4-isopropoxy-2,6-dimethyl-3-pyridinecarboxamide,
- 4-butoxy-N-(2,6-diethylphenyl)-2,6-dimethyl-3-pyridinecarboxamide,
- N-(2,6-diethylphenyl)-4-isobutoxy-2,6-dimethyl-3-pyridinecarboxamide,
- N-(2,6-diethylphenyl)-2,6-dimethyl-4-pentyloxy-3-pyridinecarboxamide,
- 5-bromo-N-(2,6-diethylphenyl)-2,6-dimethyl-4-propoxy-3-pyridinecarboxamide,
- 6-methyl-N-(2,3-dimethylphenyl)-2-phenyl-4-propoxy-3-pyridinecarboxamide,
- N-(2,6-diethylphenyl)-6-methyl-2-phenyl-4-propoxy-3-pyridinecarboxamide,
- 5-bromo-N-(4-bromo-2,6-diethylphenyl)-2,6-dimethyl-4-propoxy-3-pyridinecarboxamide,
- 2-ethyl-N-(2,6-diethylphenyl)-6-methyl-4-propoxy-3-pyridinecarboxamide,
- N-(2,6-diethylphenyl)-2,5,6-trimethyl-4-propoxy-3-pyridinecarboxamide,
- 2,6-diethyl-N-(2,6-diethylphenyl)-4-propoxy-3-pyridinecarboxamide,
- or N-(2,6-diethylphenyl)-4-isobutoxy-5,6-dimethyl-2-propyl-3-pyridinecarboxamide, or their respective 1-oxides or addition salts.
Priority Claims (3)
| Number |
Date |
Country |
Kind |
| 60-7665 |
Jan 1985 |
JPX |
|
| 60-171673 |
Aug 1985 |
JPX |
|
| 60-211821 |
Sep 1985 |
JPX |
|
US Referenced Citations (2)
| Number |
Name |
Date |
Kind |
| 3535328 |
Zielinski |
Oct 1970 |
|
| 4566899 |
Ambrosi et al. |
Jan 1986 |
|
Foreign Referenced Citations (1)
| Number |
Date |
Country |
| 1115278 |
Dec 1981 |
CAX |
