Claims
- 1. A compound of the formula: ##STR10## wherein: R is a group --(CH.sub.2)n--R.sub.1, wherein n is an integer from 1 to 3 and R.sub.1 is hydrogen, hydroxy, lower alkoxy, mercapto, lower alkylthio, amino, di-lower alkylamino, C.sub.3-11 alkyl, lower alkenyl, lower alkynyl, C.sub.3-6 cycloalkyl or phenyl substituted by halogen, lower alkyl or lower alkoxy;
- R.sub.2 and R.sub.7 are different and may each be hydrogen, C.sub.1-11 alkyl, lower alkenyl, lower alkynyl, cycloalkyl, phenyl, or phenyl substituted by halogen, lower alkyl, lower alkoxy, trihalomethyl, nitro or cyano;
- R.sub.3, R.sub.4 and R.sub.5 are, independently, hydrogen, halogen, cyano, nitro, amino, lower alkyl, lower haloalkyl, hydroxy, lower alkoxy, phenyloxy, carboxy or lower alkoxycarbonyl;
- R.sub.6 is hydrogen or halogen; and addition salts thereof with acids or bases.
- 2. The compound of claim 1, wherein ##STR11## is phenyl, 2-methylphenyl, 2-chlorophenyl, 2,3-dimethylphenyl, 2,6-dimethylphenyl, 2,6-diethylphenyl, 2,6-diethyl-4-substituted (halo, cyano, nitro, amino, lower alkyl, lower haloalkyl, hydroxy, lower alkoxy, phenyloxy, carboxy or lower alkoxy carbonyl) phenyl or 2-ethyl-6-methylphenyl.
- 3. The compound of claim 1, wherein ##STR12## is 2-chloro-6-methylphenyl, 3-chloro-2-methylphenyl, 2-ethylphenyl, 2-3-dichlorophenyl, 2,4-dichlorophenyl, 2-5-dichlorophenyl, or 2,6-dichlorophenyl.
- 4. The compound of claim 1, wherein the R.sub.2 alkyl, lower alkenyl or lower alkynyl group has from 2 to 5 carbon atoms.
- 5. The compound of claim 1, wherein R.sub.6 is hydrogen or bromine.
- 6. The compound of claim 1, wherein R.sub.7 is methyl or ethyl.
- 7. The compound of claim 1, wherein --(CH.sub.2).sub.n --R.sub.1 is methyl, ethyl, propyl, butyl, isobutyl, pentyl, isopentyl or hexyl.
- 8. The compound of claim 1, wherein --(CH.sub.2).sub.n --R.sub.1 is 2-methoxyethyl, 2-ethoxyethyl, 3-methoxypropyl or 3-ethoxypropyl.
- 9. The compound of claim 1, wherein --(CH.sub.2).sub.n --R.sub.1 is allyl or 2-propynyl.
- 10. The compound of claim 1, wherein --(CH.sub.2).sub.n --R.sub.1 is phenylmethyl, substituted phenylmethyl, 2-phenylethyl, 2-(substituted phenyl) ethyl or 3-phenylpropyl.
- 11. A compound of claim 1, which is
- 2-ethyl-1,4-dihydro-6-methyl-4-oxo-N-phenyl-1-phenylmethyl-3-pyridinecarboxamide,
- 2-ethyl-1,4-dihydro-6-methyl-1-(4-methylphenylmethyl)-N-phenyl-4-oxo-3-pyridinecarboxamide,
- 1. 4-dihydro-6-methyl-4-oxo-N-phenyl-1-phenylmethyl-2-propyl-3-pyridinecarboxamide,
- 2-butyl-1,4-dihydro-6-methyl-4-oxo-N-phenyl-1-phenylmethyl-3-pyridinecarboxamide,
- 2-butyl-1,4-dihydro-6-methyl-1-(4-methylphenylmethyl)-4-oxo-N-phenyl-3-pyridinecarboxamide,
- 1,4-dihydro-6-methyl-2-(2-methylpropyl)-4-oxo-N-phenyl-1-phenylmethyl-3-pyridinecarboxamide,
- 1,4-dihydro-6-methyl-4-oxo-2-pentyl-N-phenyl-1-phenylmethyl-3-pyridinecarboxamide,
- 1,4-dihydro-1-(3-methoxypropyl)-6-methyl-4-oxo-N,2-diphenyl-3-pyridinecarboxamide,
- 1,4-dihydro-1-(2-methoxyethyl)-6-methyl-4-oxo-N,2-diphenyl-3-pyridinecarboxamide,
- 1,4-dihydro-6-methyl-4-oxo-N,2-diphenyl-1-phenylmethyl-3-pyridinecarboxamide,
- 1,4-dihydro-6-methyl-1-(4-methylphenylmethyl)-4-oxo-N,2-diphenyl-3-pyridinecarboxamide,
- 1-(4-chlorophenylmethyl)-1,4-dihydro-6-methyl-4-oxo-N,2-diphenyl-3-pyridinecarboxamide,
- 2-(3-chlorophenyl)-1,4-dihydro-6-methyl-4-oxo-N-phenyl-1-phenylmethyl-3-pyridinecarboxamide,
- 1,4-dihydro-6-methyl-N-(2-methylphenyl)-4-oxo-1-phenylmethyl-2-propyl-3-pyridinecarboxamide,
- 1-(4-chlorophenylmethyl)-1,4-dihydro-6-methyl-N-(2-methylphenyl)-4-oxo-1-propyl-3-pyridinecarboxamide,
- 1. 4-dihydro-6-methyl-N-(2-methylphenyl)-4-oxo-2-phenyl-1-phenylmethyl-3-pyridinecarboxamide,
- 1-(4-chlorophenylmethyl)-1,4-dihydro-6-methyl-N-(2-methylphenyl)-4-oxo-2-phenyl-3-pyridinecarboxamide,
- 1,4-dihydro-6-methyl-N-(2,3-dimethylphenyl)-4-oxo-2-phenyl-1-phenylmethyl-3-pyridinecarboxamide,
- 1,4-dihydro-6-methyl-N-(2,6-dimethylphenyl)-4-oxo-2-phenyl-1-phenylmethyl-3-pyridinecarboxamide,
- 6-ethyl-1,4-dihydro-2-methyl-4-oxo-N-phenyl-1-phenylmethyl-3-pyridinecarboxamide,
- 6-ethyl-N-(2,6-diethylphenyl)-1,4-dihydro-2-methyl-4-oxo-1-(2-phenylethyl)-3-pyridinecarboxamide, or
- 5-bromo-6-ethyl-N-(2,6-diethylphenyl)-1,4-dihydro-2-methyl-4-oxo-1-(2-phenylethyl)-3-pyridinecarboxamide.
- 1-butyl-1,4-dihydro-6-methyl-4-oxo-N-phenyl-2-propyl-3-pyridinecarboxamide,
- 1-butyl-1,4-dihydro-6-methyl-4-oxo-N,2-diphenyl-3-pyridine-carboxamide,
- 1,4-dihydro-6-methyl-4-oxo-1-pentyl-N,2-diphenyl-3-pyridine-carboxamide,
- 1-hexyl-1,4-dihydro-6-methyl-4-oxo-N,2-diphenyl-3-pyridine-carboxamide,
- 1-butyl-1,4-dihydro-6-methyl-N-(2-methylphenyl)-4-oxo-2-phenyl-3-pyridinecarboxamide,
- 1-butyl-N-(2-chlorophenyl)-1,4-dihydro-6-methyl-4-oxo-2-phenyl-3-pyridinecarboxamide,
- 1-butyl-1,4-dihydro-6-methyl-N-(2,3-dimethylphenyl)-4-oxo-2-phenyl-3-pyridinecarboxamide,
- 1-butyl-1,4-dihydro-6-methyl-N-(2,6-dimethylphenyl)-4-oxo-2-phenyl-3-pyridinecarboxamide,
- 1-butyl-2-ethyl-N-(2,6-diethylphenyl)-1,4-dihydro-6-methyl-4-oxo-3-pyridinecarboxamide,
- 5-bromo-1-butyl-2-ethyl-N-(2,6-diethylphenyl)-1,4-dihydro-6-methyl-4-oxo-3-pyridinecarboxamide,
- N-(2,6-diethylphenyl)-1,4-dihydro-6-methyl-1-(2-methylphenyl)-4-oxo-2-phenyl-3pyridinecarboxamide,
- 1-butyl-6-ethyl-N-(2,6-diethylphenyl)-1,4-dihydro-2-methyl-4-oxo-3-pyridinecarboxamide,
- 1-butyl-5-bromo-6-ethyl-N-(2,6-diethylphenyl)-1,4-dihydro-2-methyl-4-oxo-3-pyridinecarboxamide,
- 2-butyl-N-(2,6-diethylphenyl)-1,4-dihydro-1,6-dimethyl-4-oxo-3-pyridinecarboxamide,
- 5-bromo-2-butyl-N-(2,6-diethylphenyl)-1,4-dihydro-1,6-dimethyl-4-oxo-3-pyridinecarboxamide,
- N-(4-bromo-2,6-diethylphenyl)-2-butyl-1,4-dihydro-1,6-dimethyl-4-oxo-3-pyridinecarboxamide,
- 5-bromo-N-(4-bromo-2,6-diethylphenyl)-2-butyl-1,4-dihydro-1,6-dimethyl-4-oxo-3-pyridinecarboxamide,
- N-(4-bromo-2,6-diethylphenyl)-1,4-dihydro-1,6-dimethyl-4-oxo-2-propyl-3-pyridinecarboxamide,
- 5-bromo-N-(4-bromo-2,6-diethylphenyl)-1,4-dihydro-1,6-dimethyl-4-oxo-2-propyl-3-pyridinecarboxamide,
- N-(2,6-diethylphenyl)-1,4-dihydro-1,6-dimethyl-4-oxo-2-propyl-3-pyridinecarboxamide,
- 5-bromo-N-(2,6-diethylphenyl)-1,4-dihydro-1,6-dimethyl-4-oxo-2-propyl-3-pyridinecarboxamide,
- N-(2,4,6-triethylphenyl)-1,4-dihydro-1,6-dimethyl-4-oxo-2-propyl-3-pyridinecarboxamide,
- 5-bromo-N-(2,4,6-triethylphenyl)-1,4-dihydro-1,6-dimethyl-4-oxo-2-propyl-3-pyridinecarboxamide,
- 6-ethyl-N-(2,6-diethylphenyl)-1,4-dihydro-1-methyl-4-oxo-2-propyl-3-pyridinecarboxamide,
- 5-bromo-N-(2,4,6-triethylphenyl)-1,4-dihydro-1,6-dimethyl-4-oxo-2-propyl-3-pyridinecarboxamide,
- 5-bromo-6-ethyl-N-(2,6-diethylphenyl)-1,4-dihydro-1-methyl-4-oxo-2-propyl-3-pyridinecarboxamide,
- N-(2,6-diethyl-4-iodophenyl)-1,4-dihydro-1,6-dimethyl-4-oxo-2-propyl-3-pyridinecarboxamide,
- 5-bromo-N-(2,6-diethyl-4-iodophenyl)-1,4-dihydro-1,6-dimethyl-4-oxo-2-propyl-3-pyridinecarboxamide,
- N-(2,6-diethyl-4-methoxyphenyl)-1,4-dihydro-1,6-dimethyl-4-oxo-2-propyl-3-pyridinecarboxamide, or
- 5-bromo-N-(2,6-diethyl-4-methoxyphenyl)-1,4-dihydro-1,6-dimethyl-4-oxo-2-propyl-3-pyridinecarboxamide.
- 12. A plant growth inhibitor composition wherein the active component consists essentially of an effective amount of the compound of claim 1 in admixture with an inert carrier.
Priority Claims (1)
Number |
Date |
Country |
Kind |
60-238524 |
Oct 1985 |
JPX |
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Parent Case Info
This is a divisional of U.S. application Ser. No. 922,038, filed Oct. 20, 1986, now U.S. Pat. No. 4,844,732.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
4777256 |
Ueda et al. |
Oct 1988 |
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Divisions (1)
|
Number |
Date |
Country |
Parent |
922038 |
Oct 1986 |
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