4-oxo pyridinecarboxamide derivatives as plant growth regulators

BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to novel compounds which belong to 1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamides. The compounds of this invention show growth inhibitory activities on plants and also anti-inflammatory activity.
2. Description of the Prior Arts
Some compounds belonging to 1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamides are found in the literature. In Yakugakuzassi, 101, 40 (1981), Kato et al. reported on four compounds, namely N-(4-chlorophenyl)-1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamide, 1,4-dihydro-2,6-dimethyl-4-oxo-N-phenyl-1-(phenylmethyl)-3-pyridinecarboxamide, 1,4-dihydro-N-(4-methoxyphenyl)-2,6-dimethyl-4-oxo-1-(phenylmethyl)-3- pyridinecarboxamide and N-(4-chlorophenyl)-1,4-dihydro-2,6-dimethyl-4-oxo-1-(phenylmethyl)-3-pyridinecarboxamide, as one of the studies on reactivity of ketene derivatives but they did not refer to utility thereof. Canadian Pat. No. 1,115,278 [and also J. B. Pierce et al, J. Med. Chem. 25, 131(1982)], there are disclosed 4-pyridone compounds possessing anti-inflammatory activity, i.e., 1,4-dihydro-2,6-dimethyl-4-oxo-N, 1-diphenyl-3-pyridinecarboxamide, N,1-dibutyl-1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamide, N,1-didodecyl-1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamide, N-(4-chlorophenyl)-1-ethyl-1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamide, etc.
On the other hand, 1,4-dihydro-4-oxo-3-pyridinecarboxylic acid derivatives as compounds which show plant growth regulating activity, especially chemical hybridizing activity, are known in Japanese Patent Unexamined Publication Nos. Sho 52(1977)-144,676 (see also U.S. Pat. No. 4,051,142) and Sho 57(1982)-114,573 (see also E.P. No. 40,082). However, plant growth inhibitory agents whose active ingredients are 1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamides as in the formula (I) shown below are not known.
SUMMARY OF THE INVENTION
This invention provides compounds of the formula (I) and salts thereof. ##STR2##
In the formula (I),
R is hydrogen atom, alkoxy group, aralkyloxy group or a group of --(CH.sub.2).sub.n --R.sub.1 wherein n is an integer from 1 to 3 and R.sub.1 is hydrogen atom, hydroxy group, lower alkoxy group, mercapto group, lower alkylthio group, amino group, di-lower alkylamino group, C.sub.3-11 alkyl group, lower alkenyl group, lower alkynyl group, cycloalkyl group, 5- or 6-membered heterocyclic group, or aryl group which may be substituted by one or two substituents of halogen, lower alkyl or lower alkoxy;
R.sub.2 is halogen atom, lower alkyl group, hydroxy group, lower alkoxy group, aryloxy group, carboxy group or lower alkoxycarbonyl group;
R.sub.3 is hydrogen atom, halogen atom or lower alkyl group.
DESCRIPTION OF PREFERRED EMBODIMENTS
The term "lower" used for lower alkyl, lower alkoxy or like group in this invention means a group containing 1-5 carbon atoms. Specifically, there may be mentioned as lower alkyl group methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl or isopentyl; as lower alkoxy group methoxy, ethoxy, propoxy, isopropoxy or butoxy; as lower alkoxycarbonyl group methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl or butoxycarbonyl; or as lower alkylthio group methylthio, ethylthio, propylthio, isopropylthio, butylthio or pentylthio. As lower alkenyl or lower alkynyl group may be mentioned vinyl, allyl, isopropenyl, 2-butenyl, 1,3-butadienyl, 2-pentenyl, 1,4-pentadienyl, 1,6-heptadienyl, 1-hexenyl, ethynyl or 2-propynyl.
Examples of alkoxy and aralkyloxy group as used in the definition of R include alkoxy groups containing 1-12 carbon atoms such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, pentyloxy, 2-methylbutoxy, hexyloxy, 2 (or 3)-methylpentyloxy, octyloxy, nonyloxy, decyloxy, dodecyloxy; aralkyloxy groups such as phenylmethoxy, phenethyloxy, phenylpropoxy or phenylbutoxy group which may be substituted by an alkyl or a halogen atom at the aryl ring.
Examples of cycloalkyl group include cyclopropyl, cyclopentyl and cyclohexyl.
Examples of the aryl group include phenyl and naphthyl.
Halogen atom includes chlorine, bromine and fluorine atom.
5- or 6-membered heterocyclic group includes 5- or 6-membered one containing one to three hetero atoms selected from nitrogen atom, oxygen atom and sulfur atom. The examples of the 5-membered heterocyclic group are furyl, tetrahydrofuryl, thienyl, thiazolyl, isothiazolyl, oxazolyl, isooxazolyl or pyrazolyl and the 6-membered heterocyclic group pyridyl, pyrimidinyl, pyrazinyl or pyridazinyl. These heterocyclic groups may be substituted by alkyl as methyl or ethyl, halogen atom or phenyl. When the heterocyclic group is substituted by phenyl, it may form a condensed ring combining the two adjacent carbon atoms in the heterocyclic group with phenyl group. Examples of the condensed ring are benzothiazolyl, benzofuryl, quinazolinyl or quinoxalinyl group.
The compound of the formula (I) in this invention may form an addition salt with an acid such as hydrochloric acid, sulfuric acid, phosphoric acid, methanesulfonic acid, p-toluenesulfonic acid or trifluoroacetic acid when sufficiently basic, and also form a salt with an inorganic base when it contains a carboxylic group. Such salts are also included in this invention.
The compound of the formula (I) in this invention may be prepared by any of the following methods.
Method A ##STR3## [R, R.sub.2 and R.sub.3 of the formula (II) are the same as those in the formula (I).]
This method comprises reacting a 3-aminocrotonic acid anilide derivative (II) or its tautomer with 2,2,6-trimethyl-4H-1,3-dioxin-4-one in an appropriate solvent (e.g., toluene or xylene) under heating at a temperature of e.g., 100.degree. C.-140.degree. C. 2-Ethyl-2,6-dimethyl-4H-1,3-dioxin-4-one is also useful in place of 2,2,6-trimethyl-4H-1,3-dioxin-4-one. Also, in this method, 3-aminocrotonic acid anilide derivative (II) is not necessarily required to be in its isolated form but may be in the form of the crude reaction mixture of an amine of the formula (III) with a compound of the formula (IV) ##STR4## [R, R.sub.2 and R.sub.3 in the formula (III) and (IV) are the same as those in the formula (I).] For the practical purpose it is convenient to use the crude reaction mixture as such.
(Method B) ##STR5## [R, R.sub.2 and R.sub.3 in the formula (III) and (V) are the same as those in the formula (I).]
This method comprises reacting a 4-pyrone compound (V) corresponding to the formula (I), i.e., 2,6-dimethyl-4-oxo-N-phenyl-4H-pyran-3-carboxamide with ammonia or an amine of the formula (III) or a salt thereof in an appropriate solvent (e.g., ethanol or water) at a temperature from room temperature to about 60.degree. C. The amount of ammonia or the amine employed is equimolecular or more to the 4-pyrone compound or a large excess if needed. When the amine is used as its available salt, it is required to convert to its free form by addition of an organic or an inorganic base in an amount needed for neutralization or more.
(Method C) ##STR6## [R, R.sub.2 and R.sub.3 in the formula (VI) and (VII) are the same meaning as defined in the formula (I).]
This method comprises reacting a carboxylic acid corresponding to the formula (I), i.e., 1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxylic acid derivative (VI) with an aniline derivative (VII) in the presence of a condensing agent for dehydration. It is advantageous to use as the condensing agent for dehydration 1-substituted-2-halopyridinium salt and a tertiary amine according to the method described in e.g. Japanese Patent Unexamined Publication No. Sho 52(1977)-57,102.
(Method D)
This method is applicable to preparation of the compound of the formula (I) wherein R is hydrogen atom and comprises treating 1,4-dihydro-2,6-dimethyl-4-oxo-N-phenyl-1-(phenylmethyl)-3-pyridinecarboxamide under conditions of hydrogenolysis to convert into 1,4-dihydro-2,6-dimethyl-4-oxo-N-phenyl-3-pyridinecarboxamide. As the preferred reaction conditions, it is especially suitable to use a solvent of an alcohol such as methanol or ethanol, a hydrogen donor such as hydrogen gas or formic acid and a catalyst of palladium-carbon or palladium-black.
This invention is illustrated further by examples hereinafter. Also, growth-inhibitory activities on plants of the compounds of the invention are shown in reference examples.
Furthermore, related specific compounds in addition to the compounds shown in the examples are as follows;
1-(4-chlorophenylmethyl)-N-(2-fluorophenyl)-1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamide,
N-(2-bromophenyl)-1-(4-chlorophenylmethyl)-1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamide,
N-(3-chloro-2-methylphenyl)-1-(4-chlorophenylmethyl)-1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamide,
N-(2-fluorophenyl)-1,4-dihydro-2,6-dimethyl-1-(4-methylphenylmethyl)-4-oxo-3-pyridinecarboxamide,
N-(2-bromophenyl)-1,4-dihydro-2,6-dimethyl-1-(4-methylphenylmethyl)-4-oxo-3-pyridinecarboxamide,
1-butyl-N-(2-fluorophenyl)-1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamide,
N-(2-bromophenyl)-1-butyl-1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamide,
N-(3-chloro-2-methylphenyl)-1,4-dihydro-2,6-dimethyl-4-oxo-1-pentyl-3-pyridinecarboxamide,
N-(3-chloro-2-methylphenyl)-1-hexyl-1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamide,
N-(3-chloro-2-methylphenyl)-1-(2-ethoxyethyl)-1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamide,
N-(2-fluorophenyl)-1,4-dihydro-2,6-dimethyl-4-oxo-1-(2-phenylethyl)-3-pyridinecarboxamide,
N-(2-bromophenyl)-1,4-dihydro-2,6-dimethyl-4-oxo-1-(2-phenylethyl)-3-pyridinecarboxamide,
1,4-dihydro-2,6-dimethyl-N-(2-methylphenyl)-4-oxo-1-(2-thienylmethyl)-3-pyridinecarboxamide,
1,4-dihydro-2,6-dimethyl-N-(2,6-dimethylphenyl)-4-oxo-1-(2-thienylmethyl)-3-pyridinecarboxamide,
N-(2-ethyl-6-methylphenyl)-1,4-dihydro-2,6-dimethyl-4-oxo-1-(2-thienylmethyl)-3-pyridinecarboxamide,
1,4-dihydro-2,6-dimethyl-N-(2,3-dimethylphenyl)-4-oxo-1-(2-thienylmethyl)-3-pyridinecarboxamide,
N-(2-chloro-6-methylphenyl)-1,4-dihydro-2,6-dimethyl-4-oxo-1-phenylmethyl-3-pyridinecarboxamide,
N-(2-chloro-6-methylphenyl)-1-(4-chlorophenylmethyl)-1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamide,
N-(2-chloro-6-methylphenyl)-1,4-dihydro-2,6-dimethyl-1-(4-methylphenylmethyl)-4-oxo-3-pyridinecarboxamide,
1-(4-fluorophenylmethyl)-1,4-dihydro-2,6-dimethyl-N-(2,3-dimethylphenyl)-4-oxo-3-pyridinecarboxamide,
N-(2-ethyl-6-methylphenyl)-1-(4-fluorophenylmethyl)-1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamide,
1,4-dihydro-2,6-dimethyl-N-(2,6-dimethylphenyl)-4-oxo-1-(3-pyridylmethyl)-3-pyridinecarboxamide,
N-(2,6-diethylphenyl)-1,4-dihydro-2,6-dimethyl-4-oxo-1-(3-pyridylmethyl)-3-pyridinecarboxamide,
1-butyl-1,4-dihydro-N-(2-methoxycarbonylphenyl)-2,6-dimethyl-4-oxo-3-pyridinecarboxamide,
N-(2-ethylphenyl)-1-hexyl-1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamide,
1-(2-ethoxyethyl)-N-(2-ethylphenyl)-1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamide,
1-[2-(4-chlorophenyl)ethyl]-N-(2-ethylphenyl)-1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamide,
1,4-dihydro-2,6-dimethyl-N-(2,4-dimethylphenyl)-4-oxo-1-pentyl-3-pyridinecarboxamide,
1-hexyl-1,4-dihydro-2,6-dimethyl-N-(2,4-dimethylphenyl)-4-oxo-3-pyridinecarboxamide,
1-(2-ethoxyethyl)-1,4-dihydro-2,6-dimethyl-N-(2,4-dimethylphenyl)-4-oxo-3-pyridinecarboxamide,
1,4-dihydro-2,6-dimethyl-N-(2,5-dimethylphenyl)-4-oxo-1-pentyl-3-pyridinecarboxamide,
1-hexyl-1,4-dihydro-2,6-dimethyl-N-(2,5-dimethylphenyl)-4-oxo-3-pyridinecarboxamide,
1-(2-ethoxyethyl)-1,4-dihydro-2,6-dimethyl-N-(2,5-dimethylphenyl)-4-oxo-3-pyridinecarboxamide,
1-[2-(4-chlorophenyl)ethyl]-1,4-dihydro-2,6-dimethyl-N-(2,6-dimethylphenyl)-4-oxo-3-pyridinecarboxamide,
1,4-dihydro-2,6-dimethyl-N-(2,6-dimethylphenyl)-4-oxo-1-(3-phenylpropyl)-3-pyridinecarboxamide,
1,4-dihydro-2,6-dimethyl-N-(2,6-dimethylphenyl)-1-[2-(4-methylphenyl)ethyl]-4-oxo-3-pyridinecarboxamide,
1-[2-(4-chlorophenyl)ethyl]-N-(2-ethyl-6-methylphenyl)-1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamide,
N-(2-ethyl-6-methylphenyl)-1,4-dihydro-2,6-dimethyl-4-oxo-1-(3-phenylpropyl)-3-pyridinecarboxamide,
N-(2-ethyl-6-methylphenyl)-1,4-dihydro-2,6-dimethyl-1-[2-(4-methylphenyl)ethyl]-4-oxo-3-pyridinecarboxamide,
N-(3-chloro-2-methylphenyl)-1-[2-(4-chlorophenyl)ethyl]-1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamide,
N-(5-chloro-2-methylphenyl)-1,4-dihydro-2,6-dimethyl-4-oxo-1-pentyl-3-pyridinecarboxamide,
N-(5-chloro-2-methylphenyl)-1-hexyl-1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamide,
N-(5-chloro-2-methylphenyl)-1-(2-ethoxyethyl)-1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamide,
N-(2-chloro-6-methylphenyl)-1,4-dihydro-2,6-dimethyl-4-oxo-1-pentyl-3-pyridinecarboxamide,
N-(2-chloro-6-methylphenyl)-1-hexyl-1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamide,
N-(2-chloro-6-methylphenyl)-1-(2-ethoxyethyl)-1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamide,
N-(2-chlorophenyl)-1-[2-(4-chlorophenyl)ethyl]-1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamide,
N-(2,5-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-4-oxo-1-pentyl-3-pyridinecarboxamide,
N-(2,5-dichlorophenyl)-1-hexyl-1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamide,
N-(2,5-dichlorophenyl)-1-(2-ethoxyethyl)-1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamide,
N-(2,6-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-4-oxo-1-pentyl-3-pyridinecarboxamide,
N-(2,6-dichlorophenyl)-1-hexyl-1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamide,
N-(2,6-dichlorophenyl)-1-(2ethoxyethyl)-1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamide,
N-(2,6-dichlorophenyl)-1-[2-(4-chlorophenyl)ethyl]-1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamide,
N-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-4-oxo-1-propyl-3-pyridinecarboxamide.

EXAMPLE 1
N-(2-chlorophenyl)-1-(4-chlorophenylmethyl)-1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamide ##STR7##
(Method A)
A mixture of 2.40 g (11.3 m mol) of N-(2-chlorophenyl)-3-oxo-butanamide, 1.61 g (11.3 m mol) of 4-chlorobenzylamine and 50 ml of toluene was refluxed for 1.5 hours, while the resulting water was removed through a Dean-Stark's water-separator. To the mixture was dropwise added a solution of 4.07 g (28.6 m mol) of 2,2,6-trimethyl-4H-1,3-dioxin-4-one in 10 ml of toluene within about 30 minutes. After refluxing further for one hour, the reaction mixture was cooled at room temperature to precipitate crystals of the title compound. The crystals separated by filtration were dried under vacuo to afford 3.19 g (yield: 70%) of the product having mp. 172.5.degree.-175.degree. C.
EXAMPLE 2
N-(2,6-diethylphenyl)-1,4-dihydro-2,6-dimethyl-1-(2-dimethylaminoethyl)-4-oxo-3-pyridinecarboxamide ##STR8##
(Method B)
To a solution of 1.50 g (5.0 m mol) of N-(2,6-diethylphenyl)-2,6-dimethyl-4-oxo-4H-pyran-3-carboxamide (mp. 83.5.degree.-84.5.degree. C.) in 25 ml of ethanol and 5 ml of water was added 8.82 g (100 m mol) of N,N-dimethylethylenediamine, and stirred for 7 hours at room temperature. The reaction mixture was concentrated under vacuo and the solid residue was recrystallized from isopropyl ether to give 1.51 g (yield: 82%) of the title compound having mp. 121.degree.-122.degree. C.
EXAMPLE 3
1,4-dihydro-2,6-dimethyl-N-(2-methylphenyl)-4-oxo1-phenylmethyl-3-pyridinecarboxamide ##STR9##
(Method C)
To a solution of 2.41 g (10.0 m mol) of 1,4-dihydro-2,6-dimethyl-4-oxo-1-phenylmethyl-3-pyridinecarboxylic acid and 3.60 g (12 m mol) of 2-chloro-1-methyl-pyridinium tosylate dissolved in 50 ml of chloroform, was added 2.43 g (24 m mol) of triethylamine and stirred for 30 minutes at room temperature. 1.10 g (10.3 m mol) of o-toluidine was added to the reaction mixture followed by stirring for 4 hours at room temperature. The reaction mixture, transferred to a separatory funnel, was washed with a saturated sodium bicarbonate solution. The organic layer was dried and concentrated in an usual manner to obtain a solid residue. The residue was recrystallized from toluene to give 0.78 g (yield: 21.5%) of the title compound having mp. 170.5.degree.-174.degree. C.
EXAMPLE 4
1,4-dihydro-2,6-dimethyl-N-(2,6-dimethylphenyl)-4-oxo-3-pyridinecarboxamide ##STR10##
(Method D)
To a solution of 3.00 g (8.32 m mol) of 1,4-dihydro-2,6-dimethyl-N-(2,6-dimethylphenyl)-4-oxo-1-phenylmethyl-3-pyridinecarboxamide in 100 ml of methanol and 10 ml of formic acid was added 0.60 g of 5% Pd/C as a catalyst and the mixture was stirred for 4 hours at room temperature under nitrogen atmosphere. After removing the catalyst by filtration the filtrate was concentrated to obtain a residue, which was recrystallized from a mixture of ethyl acetate and acetone, affording 1.87 g (yield: 83%) of the title compound having mp. 239.degree.-241.degree. C.
The following Table 1 and Table 2 show physical properties of the compounds associated with this invention. Numbers in the column "Evaluation" in Table 2 were obtained as follows.
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 Melting PointNo. R R.sub.2 R.sub.3 Method (.degree.C.) Molecular Formula__________________________________________________________________________ 1 4-chlorophenylmethyl Cl H A 172.5-175 C.sub.21 H.sub.18 Cl.sub.2 N.sub.2 O.sub.2 2 2-dimethylaminoethyl C.sub.2 H.sub.5 6-C.sub.2 H.sub.5 B 121-122 C.sub.22 H.sub.31 N.sub.3 O.sub.2 3 phenylmethyl CH.sub.3 H C 170.5-174 C.sub.22 H.sub.22 N.sub.2 O.sub.2 4 H CH.sub.3 6-CH.sub.3 D 239-241 C.sub.16 H.sub.18 N.sub.2 O.sub.2 5 H CH.sub.3 H D 237-238 C.sub.15 H.sub.16 N.sub.2 O.sub.2 6 butyl " H A 143-145 C.sub.19 H.sub.24 N.sub.2 O.sub.2 7 3-chlorophenylmethyl " H A 193-195 C.sub.22 H.sub.21 ClN.sub.2 O.sub.2 8 4-chlorophenylmethyl " H A 170-172 C.sub.22 H.sub.21 ClN.sub.2 O.sub.2 9 2-fluorophenylmethyl " H A 205-207 C.sub.22 H.sub.21 FN.sub.2 O.sub. 2 10 4-fluorophenylmethyl " H A 188-189 C.sub.22 H.sub.21 FN.sub.2 O.sub.2 11 3,4-dichlorophenylmethyl CH.sub.3 H A 219-221 C.sub.22 H.sub.20 Cl.sub.2 N.sub.2 O.sub.2 12 3-methoxyphenylmethyl " " A 204-205.5 C.sub.23 H.sub.24 N.sub.2 O.sub.3 13 3-methylphenylmethyl " " A 162-164 C.sub.23 H.sub.24 N.sub.2 O.sub.2 14 4-methylphenylmethyl " " A 130-133 C.sub.23 H.sub.24 N.sub.2 O.sub.2 15 4-isopropylphenylmethyl " " A 161-163 C.sub.25 H.sub.28 N.sub.2 O.sub.2 16 4-t-butylphenylmethyl " " A 190.5-194 C.sub.26 H.sub.30 N.sub.2 O.sub.2 17 2-furylmethyl " " A 147-149 C.sub.20 H.sub.20 N.sub.2 O.sub.3 18 4-pyridylmethyl " " A 145-147 C.sub.21 H.sub.21 N.sub.3 O.sub.2 19 2-phenylethyl " " A 158-159.5 C.sub.23 H.sub.24 N.sub.2 O.sub.2 20 butyl C.sub.2 H.sub.5 " A 161.5-163.5 C.sub. 20 H.sub.26 N.sub.2 O.sub.2 21 phenylmethyl C.sub.2 H.sub.5 H A 166-169 C.sub.23 H.sub.24 N.sub.2 O.sub.2 22 4-chlorophenylmethyl " " A 190-191 C.sub.23 H.sub.23 ClN.sub.2 O.sub.2 23 4-methylphenylmethyl " " A 179.5-183 C.sub.24 H.sub.26 N.sub.2 O.sub.2 24 H CH.sub.3 3-CH.sub.3 D 217-218 C.sub.16 H.sub.18 N.sub.2 O.sub.2 25 butyl " " A 137-139 C.sub.20 H.sub.26 N.sub.2 O.sub.2 26 phenylmethyl " " A 201-205 C.sub.23 H.sub.24 N.sub.2 O.sub.2 27 2-chlorophenylmethyl " " A -- C.sub.23 H.sub.23 ClN.sub.2 O.sub.2 28 3-chlorophenylmethyl " " A 233.5-236.5 C.sub.23 H.sub.23 ClN.sub.2 O.sub.2 29 4-chlorophenylmethyl " " A -- C.sub.23 H.sub.23 ClN.sub.2 O.sub.2 30 3,4-dichlorophenylmethyl " " A 253-255 C.sub.23 H.sub.22 Cl.sub.2 N.sub.2 O.sub.2 31 2-fluorophenylmethyl CH.sub.3 3-CH.sub.3 A 227.5- 229 C.sub.23 H.sub.23 FN.sub.2 O.sub.2 32 2-methoxyphenylmethyl " " A -- C.sub.24 H.sub.26 N.sub.2 O.sub.3 33 3-methoxyphenylmethyl " " A 199-204 C.sub.24 H.sub.26 N.sub.2 O.sub.3 34 4-methoxyphenylmethyl " " A 158-160.5 C.sub.24 H.sub.26 N.sub.2 O.sub.3 35 3-methylphenylmethyl " " A 203.5-209.5 C.sub.24 H.sub.26 N.sub.2 O.sub.2 36 4-methylphenylmethyl " " A 175-176.5 C.sub.24 H.sub.26 N.sub.2 O.sub.2 37 4-isopropylphenylmethyl " " A 197-199 C.sub.26 H.sub.30 N.sub.2 O.sub.2 38 4-t-butylphenylmethyl " " A 204-206 C.sub.27 H.sub.32 N.sub.2 O.sub.2 39 2-pyridylmethyl " " A 189.5-191.5 C.sub.22 H.sub.23 N.sub.3 O.sub.2 40 butyl " 4-CH.sub.3 A 160-162 C.sub.20 H.sub.26 N.sub.2 O.sub.2 41 phenylmethyl CH.sub.3 4-CH.sub.3 A 202.5-208.5 C.sub.23 H.sub.24 N.sub.2 O.sub.2 42 4-chlorophenylmethyl " " A 202-206 C.sub.23 H.sub.23 ClN.sub.2 O.sub.2 43 4-methylphenylmethyl " " A 172-177 C.sub.24 H.sub.26 N.sub.2 O.sub.2 44 phenylmethyl " 5-CH.sub.3 A 171-175.5 C.sub.23 H.sub.24 N.sub.2 O.sub.2 45 butyl " 6-CH.sub.3 A 195-202 C.sub.20 H.sub.26 N.sub.2 O.sub.2 46 hexyl " " A 119-120.5 C.sub.22 H.sub.30 N.sub.2 O.sub.2 47 allyl " " A 144-146 C.sub.19 H.sub.22 N.sub.2 O.sub.2 48 phenylmethyl " " A 184-188 C.sub.23 H.sub.24 N.sub.2 O.sub.2 49 2-chlorophenylmethyl " " A 194-198 C.sub.23 H.sub.23 ClN.sub.2 O.sub.2 50 3-chlorophenylmethyl " " A 190-193 C.sub.23 H.sub.23 ClN.sub.2 O.sub.2 51 4-chlorophenylmethyl CH.sub.3 6-CH.sub.3 A 176-179 C.sub.23 H.sub.23 ClN.sub.2 O.sub.2 52 2,4-dichlorophenylmethyl " " A 191.5-193 C.sub.23 H.sub.22 Cl.sub.2 N.sub.2 O.sub. 2 53 3,4-dichlorophenylmethyl " " A 190-192.5 C.sub.23 H.sub.22 Cl.sub.2 N.sub.2 O.sub.2 54 4-isopropylphenylmethyl " " A 192-194 C.sub.26 H.sub.30 N.sub.2 O.sub.2 55 2-phenylethyl " " A 190-192 C.sub.24 H.sub.26 N.sub.2 O.sub.2 56 4-fluorophenylmethyl " " A 107-109 C.sub.23 H.sub.23 FN.sub.2 O.sub.2 57 2-methoxyphenylmethyl " " A -- C.sub.24 H.sub.26 N.sub.2 O.sub.3 58 3-methoxyphenylmethyl " " A 192.5-195 C.sub.24 H.sub.26 N.sub.2 O.sub.3 59 4-methoxyphenylmethyl " " A 183-185 C.sub.24 H.sub.26 N.sub.2 O.sub.3 60 3-methylphenylmethyl " " A 174-176 C.sub.24 H.sub.26 N.sub.2 O.sub.2 61 4-methylphenylmethyl CH.sub.3 6-CH.sub.3 A 229-232.5 C.sub.24 H.sub.26 N.sub.2 O.sub.2 62 4-t-butylphenylmethyl " " A 205-207 C.sub.27 H.sub.32 N.sub.2 O.sub.2 63 2-furylmethyl " " A 130.5-133 C.sub. 21 H.sub.22 N.sub.2 O.sub.3 64 2-pyridylmethyl " " A 151-154 C.sub.22 H.sub.23 N.sub.3 O.sub.2 65 2-phenylethyl C.sub.2 H.sub.5 " A 144-146 C.sub.25 H.sub.28 N.sub.2 O.sub.2 66 butyl " " A 133-135 C.sub.21 H.sub.28 N.sub.2 O.sub.2 67 allyl " " A 141-143 C.sub.20 H.sub.24 N.sub.2 O.sub.2 68 phenylmethyl " " A 150.5-153 C.sub.24 H.sub.26 N.sub.2 O.sub.2 69 3-chlorophenylmethyl " " A 113-115 C.sub.24 H.sub.25 ClN.sub.2 O.sub.2 70 4-chlorophenylmethyl " " A 169-171 C.sub.24 H.sub.25 ClN.sub.2 O.sub.2 71 3-methoxyphenylmethyl C.sub.2 H.sub.5 6-CH.sub.3 A 112-115 C.sub.25 H.sub.28 N.sub.2 O.sub.3 72 3-methylphenylmethyl " " A 125-128 C.sub.25 H.sub.28 N.sub.2 O.sub.2 73 4-methylphenylmethyl " " A 146.5-151 C.sub.25 H.sub.28 N.sub.2 O.sub.2 74 H " 6-C.sub.2 H.sub.5 D 187-189 C.sub.18 H.sub.22 N.sub.2 O.sub.2 75 methyl " " B 130-132 C.sub.19 H.sub.24 N.sub.2 O.sub.2 76 ethyl " " B 115-116 C.sub.20 H.sub.26 N.sub.2 O.sub.2 77 propyl " " A 116-118 C.sub.21 H.sub.28 N.sub.2 O.sub.2 78 butyl " " A 120-121.5 C.sub.22 H.sub.30 N.sub.2 O.sub.2 79 2-methylpropyl " " A 136.5-138 C.sub.22 H.sub.30 N.sub.2 O.sub.2 80 pentyl " " A 96-98 C.sub.23 H.sub.32 N.sub.2 O.sub.2 81 3-methylbutyl C.sub.2 H.sub.5 6-C.sub.2 H.sub.5 A 128-130 C.sub.23 H.sub.32 N.sub.2 O.sub.2 82 hexyl " " A 109-110 C.sub.24 H.sub.34 N.sub.2 O.sub.2 83 octyl " " A oil - C.sub.26 H.sub.38 N.sub.2 O.sub.2 84 2-ethylhexyl " " A oil - C.sub.26 H.sub.38 N.sub. 2 O.sub.2 85 dodecyl " " A 75-80 C.sub.30 H.sub.16 N.sub.2 O.sub.2 86 cyclohexylmethyl " " A 154-154.5 C.sub.25 H.sub.34 N.sub.2 O.sub.2 87 allyl " " A 154-156 C.sub.21 H.sub.26 N.sub.2 O.sub.2 88 2-propynyl " " A 159-161 C.sub.21 H.sub.21 N.sub.2 O.sub.2 89 phenylmethyl " " A 142-146.5 C.sub.25 H.sub.28 N.sub.2 O.sub.2 90 2-chlorophenylmethyl " " A -- C.sub.25 H.sub.27 ClN.sub.2 O.sub.2 91 4-chlorophenylmethyl C.sub.2 H.sub.5 6-C.sub.2 H.sub.5 A 174-176.5 C.sub.25 H.sub.27 ClN.sub.2 O.sub.2 92 2,4-dichlorophenylmethyl " " A -- C.sub.25 H.sub.26 Cl.sub.2 N.sub.2 O.sub.2 93 3,4-dichlorophenylmethyl " " A -- C.sub.25 H.sub.26 Cl.sub.2 N.sub.2 O.sub.2 94 2-fluorophenylmethyl " " A 146.5-150.5 C.sub.25 H.sub.27 FN.sub.2 O.sub.2 95 4-fluorophenylmethyl " " A 153-155 C.sub.25 H.sub.27 FN.sub.2 O.sub.2 96 3-methoxyphenylmethyl " " A 120-122 C.sub.26 H.sub.30 N.sub.2 O.sub.3 97 4-methoxyphenylmethyl " " A 160-162 C.sub.26 H.sub.30 N.sub.2 O.sub.3 98 3-methylphenylmethyl " " A 128-129 C.sub.26 H.sub.30 N.sub.2 O.sub.2 99 4-methylphenylmethyl " " A 165-167 C.sub.26 H.sub.30 N.sub.2 O.sub.2100 2-furylmethyl " " A 146-148 C.sub.23 H.sub.26 N.sub.2 O.sub.3101 2-pyridylmethyl C.sub.2 H.sub.5 6-C.sub.2 H.sub.5 A 179-184.5 C.sub.24 H.sub.27 N.sub.3 O.sub.2102 2-tetrahydrofurylmethyl " " A 115-117 C.sub.23 H.sub.30 N.sub.2 O.sub.3103 2-phenylethyl " " A 113-115 C.sub.26 H.sub.30 N.sub.2 O.sub.2104 2-hydroxyethyl " " B 203-205 C.sub.20 H.sub.26 N.sub.2 O.sub.3105 2-methoxyethyl " " A -- C.sub.21 H.sub.28 N.sub.2 O.sub.3106 2-ethoxyethyl " " A 115-117 C.sub.22 H.sub.30 N.sub.2 O.sub.3107 2-ethylthioethyl " " B 137-138.5 C.sub.22 H.sub.30 N.sub.2 O.sub.2 S108 3-methoxypropyl " " A 106-107 C.sub.22 H.sub.30 N.sub.2 O.sub.3109 3-ethoxypropyl " " A 88-89.5 C.sub.23 H.sub.32 N.sub.2 O.sub.3110 3-isopropoxypropyl " " A 110-111 C.sub.24 H.sub.34 N.sub.2 O.sub.3111 3-(2-ethylhexyloxy)propyl C.sub.2 H.sub.5 6-C.sub.2 H.sub.5 B -- C.sub.29 H.sub.44 N.sub.2 O.sub.3112 3-dimethylaminopropyl " " B 111-113.8 C.sub.23 H.sub.33 N.sub.3 O.sub.2113 H i-C.sub.3 H.sub.7 6-i-C.sub.3 H.sub.7 D 119-121 C.sub.20 H.sub.26 N.sub.2 O.sub.2114 allyl " " A 165-167 C.sub.23 H.sub.30 N.sub.2 O.sub.2115 phenylmethyl " " A 216-219 C.sub.27 H.sub.32 N.sub.2 O.sub.2116 4-chlorophenylmethyl " " A 206.5-207.5 C.sub.27 H.sub.31 ClN.sub.2 O.sub.2117 4-methoxyphenylmethyl " " A 204.5-209.5 C.sub.28 H.sub.34 N.sub.2 O.sub.3118 4-methylphenylmethyl " " A 198-207 C.sub.28 H.sub.34 N.sub.2 O.sub.2119 butyl Cl 6-CH.sub.3 A 147.5-150 C.sub.19 H.sub.23 ClN.sub.2 O.sub.2120 butyl CH.sub.3 5-Cl A 149-162 C.sub.19 H.sub.23 ClN.sub.2 O.sub.2121 phenylmethyl CH.sub.3 5-Cl A 148-156 C.sub.22 H.sub.21 ClN.sub.2 O.sub.2122 4-chlorophenylmethyl " " A 222-224 C.sub.22 H.sub.20 Cl.sub.2 N.sub.2 O.sub.2123 H Cl H B 264-264.5 C.sub.14 H.sub.13 ClN.sub.2 O.sub.2124 butyl " " A 185-187 C.sub.18 H.sub.21 ClN.sub. 2 O.sub.2125 3-chlorophenylmethyl " " A 192-194 C.sub.21 H.sub.18 Cl.sub.2 N.sub.2 O.sub.2126 3,4-dichlorophenylmethyl " " A 226-228 C.sub.21 H.sub.17 Cl.sub.3 N.sub.2 O.sub.2127 2-fluorophenylmethyl " " A 203-205 C.sub.21 H.sub.18 ClFN.sub.2 O.sub.2128 4-fluorophenylmethyl " " A 186-188 C.sub.21 H.sub. 18 ClFN.sub.2 O.sub.2129 3-methoxyphenylmethyl " " A 190-193 C.sub.22 H.sub.21 ClN.sub.2 O.sub.3130 4-methoxyphenylmethyl " " A 221-223 C.sub.22 H.sub.21 ClN.sub.2 O.sub.3131 3-methylphenylmethyl Cl H A 180-182 C.sub.22 H.sub.21 ClN.sub.2 O.sub.2132 4-methylphenylmethyl " " A 165-167.5 C.sub.22 H.sub.21 ClN.sub.2 O.sub.2133 4-isopropylphenylmethyl " " A 184-186 C.sub.24 H.sub.25 ClN.sub.2 O.sub.2134 4-t-butylphenylmethyl " " A 220.5-223 C.sub.25 H.sub.27 ClN.sub.2 O.sub.2135 2-furylmethyl " " A 169-171 C.sub.19 H.sub.17 ClN.sub.2 O.sub.3136 2-pyridylmethyl " " A 181-183 C.sub.20 H.sub.18 ClN.sub.3 O.sub.2137 3-pyridylmethyl " " A 195-196.5 C.sub.20 H.sub.18 ClN.sub.3 O.sub.2138 4-pyridylmethyl " " A 195-197 C.sub.20 H.sub.18 ClN.sub.3 O.sub.2139 butyl " 3-Cl A 197.5-200.5 C.sub.18 H.sub.20 Cl.sub.2 N.sub.2 O.sub.2140 4-chlorophenylmethyl " " A 227-229 C.sub.21 H.sub.17 Cl.sub.3 N.sub.2 O.sub.2141 4-methylphenylmethyl Cl 3-Cl A 201-203 C.sub.22 H.sub.20 Cl.sub.2 N.sub.2 O.sub.2142 butyl " 4-Cl A 213-215 C.sub.18 H.sub.20 Cl.sub.2 N.sub.2 O.sub.2143 phenylmethyl " " A 249-251 C.sub.21 H.sub.18 Cl.sub.2 N.sub.2 O.sub.2144 4-chlorophenylmethyl " " A 260-262 C.sub.21 H.sub.17 Cl.sub.3 N.sub.2 O.sub.2145 4-methylphenylmethyl " " A 237-239 C.sub.22 H.sub.20 Cl.sub.2 N.sub.2 O.sub.2146 2-phenylethyl " " A 203-212 C.sub.22 H.sub.20 Cl.sub.2 N.sub.2 O.sub.2147 butyl " 5-Cl A 162-164 C.sub.18 H.sub.20 Cl.sub.2 N.sub.2 O.sub.2148 phenylmethyl " " A 118-120 C.sub.21 H.sub.18 Cl.sub.2 N.sub.2 O.sub.2149 4-chlorophenylmethyl " " A 194-197 C.sub.21 H.sub.17 Cl.sub.3 N.sub.2 O.sub.2150 4-methylphenylmethyl " " A 173-174.5 C.sub.22 H.sub.20 Cl.sub.2 N.sub.2 O.sub.2151 butyl Cl 6-Cl A 169-171 C.sub.18 H.sub.20 Cl.sub.2 N.sub.2 O.sub.2152 phenylmethyl " " A 168-172.5 C.sub.21 H.sub.18 Cl.sub.2 N.sub.2 O.sub.2153 4-chlorophenylmethyl " " A 115.5-120 C.sub.21 H.sub.17 Cl.sub.3 N.sub.2 O.sub.2154 4-methylphenylmethyl " " A -- C.sub.22 H.sub.20 Cl.sub.2 N.sub.2 O.sub.2155 butyl OCH.sub.3 H A 158-160 C.sub.19 H.sub.24 N.sub.2 O.sub.3156 phenylmethyl " " A 240-242 C.sub.22 H.sub.22 N.sub.2 O.sub.3157 4-chlorophenylmethyl " " A 227.5-230.5 C.sub.22 H.sub.21 ClN.sub.2 O.sub.3158 4-methylphenylmethyl " " A 206.5-209 C.sub.23 H.sub.24 N.sub.2 O.sub.3159 phenylmethyl OPh " A 213-214.5 C.sub.27 H.sub.24 N.sub.2 O.sub.3160 4-chlorophenylmethyl " " A 232-233.5 C.sub.27 H.sub.23 ClN.sub.2 O.sub.3161 4-methylphenyl OPh H A 191.5-193 C.sub.28 H.sub. 26 N.sub.2 O.sub.3 162* phenylmethyl COOH " * 290-294 C.sub.22 H.sub.20 N.sub.2 O.sub.4 163** H COOK " ** 198-200 C.sub.14 H.sub.13 N.sub.2 O.sub.4 K 164*** phenylmethyl " " *** 210-215 C.sub.22 H.sub.19 N.sub.2 O.sub.4 K165 H COOCH.sub.3 " D 217-218 C.sub.15 H.sub.16 N.sub.2 O.sub.4166 phenylmethyl " " A 186.5-188 C.sub.23 H.sub.22 N.sub.2 O.sub.4167 4-chlorophenylmethyl " " A 190-192 C.sub.23 H.sub.21 ClN.sub.2 O.sub.4168 4-methylphenylmethyl " " A 152-153.5 C.sub.24 H.sub.21 N.sub.2 O.sub.4 *Compound 162 was obtained by treating Compound 164 with a dilute HCl. **Compound 163 was obtained by hydrolyzing Compound 165 with equimolecula KOH. ***Compound 164 was obtained by hydrolyzing Compound 166 with equimolecular KOH.
169 pentyl CH.sub.3 H A 124-125.5 C.sub.20 H.sub.26 N.sub.2 O.sub.2170 hexyl " " A 130-132 C.sub.21 H.sub.28 N.sub.2 O.sub.2171 2-ethoxyethyl " " A 99-100.5 C.sub.19 H.sub.24 N.sub.2 O.sub.3 172* phenylmethyl " " A C.sub.22 H.sub.23 ClN.sub.2 O.sub.2173 2-pyridylmethyl " " A 146-148 C.sub.21 H.sub.21 N.sub.3 O.sub.2174 3-pyridylmethyl " " A 161-163 C.sub.21 H.sub.21 N.sub.3 O.sub.2175 pentyl C.sub.2 H.sub.5 " A 144-145 C.sub.21 H.sub.28 N.sub.2 O.sub.2176 2-phenylethyl " " A 145-147 C.sub.24 H.sub.26 N.sub.2 O.sub.2177 pentyl CH.sub.3 3-CH.sub.3 A 165-167 C.sub.21 H.sub.28 N.sub.2 O.sub.2178 hexyl " " A 138.5-140.5 C.sub.22 H.sub.30 N.sub.2 O.sub.2 *Compound 172 is a hydrochloride
179 2-ethoxyethyl CH.sub.3 3-CH.sub.3 A 111.5-113 C.sub.20 H.sub.26 N.sub.2 O.sub.3180 2-phenylethyl " " A 189-191.5 C.sub.24 H.sub.26 N.sub.2 O.sub.2181 4-pyridylmethyl " " A 230-232 C.sub.22 H.sub.23 N.sub.3 O.sub.2182 2-phenylethyl " 4-CH.sub.3 A C.sub.24 H.sub.26 N.sub.2 O.sub.2183 butyl " 5-CH.sub.3 A 169-170.5 C.sub.20 H.sub.26 N.sub.2 O.sub.2184 2-phenylethyl " " A 155-157 C.sub.24 H.sub.26 N.sub.2 O.sub.2185 pentyl " 6-CH.sub.3 A 191-194 C.sub.21 H.sub.28 N.sub.2 O.sub.2186 2-ethoxyethyl " " A 105.8-107.5 C.sub.20 H.sub.26 N.sub.2 O.sub.3187 pentyl C.sub.2 H.sub.5 " A 94.8-96 C.sub.22 H.sub.30 N.sub.2 O.sub.2188 hexyl " " A oil C.sub.23 H.sub.32 N.sub.2 O.sub.2189 2-ethoxyethyl C.sub.2 H.sub.5 6-CH.sub.3 A 113-115 C.sub.21 H.sub.28 N.sub.2 O.sub.3 190* butyl " 6-C.sub.2 H.sub.5 C.sub.24 H.sub.31 F.sub.3 N.sub.2 O.sub.4 191** butyl " " C.sub.22 H.sub.31 ClN.sub.2 O.sub.2192 2-(4-chlorophenylethyl) " " A 164-166 C.sub.26 H.sub.29 ClN.sub.2 O.sub.2193 2-(2-chlorophenylethyl) " " A 125-127 C.sub.26 H.sub.29 ClN.sub.2 O.sub.2194 3-phenylpropyl " " A 147-149 C.sub.27 H.sub.32 N.sub.2 O.sub.2195 4-phenylbutyl " " A oil C.sub.28 H.sub.34 N.sub.2 O.sub.2196 2-thienylmethyl " " A 90-94.5 C.sub.23 H.sub.26 N.sub.2 O.sub.2 S197 2-(2-pyridylethyl) " " A oil C.sub.25 H.sub.29 N.sub.3 O.sub.2198 benzyl CH.sub.3 3-Cl A 187-189 C.sub.22 H.sub.21 ClN.sub.2 O.sub.2 *Compound 190 is a trifluoroacetate **Compound 191 is a hydrochloride
199 4-methylphenylmethyl CH.sub.3 3-Cl A 178-181.5 C.sub.23 H.sub.23 ClN.sub.2 O.sub.2200 butyl " 3-Cl A 170-172 C.sub.19 H.sub.23 ClN.sub.2 O.sub.2201 2-phenylethyl " " A 186-188 C.sub.23 H.sub.23 ClN.sub.2 O.sub.2202 2-phenylethyl " 5-Cl A 177.5-179.5 C.sub.23 H.sub.23 ClN.sub.2 O.sub.2203 2-phenylethyl Cl 6-CH.sub.3 A 173.5-175 C.sub.23 H.sub.23 ClN.sub.2 O.sub.2204 pentyl " H A 188-189.5 C.sub.19 H.sub.23 ClN.sub.2 O.sub.2205 hexyl " " A 165-167 C.sub.20 H.sub.25 ClN.sub.2 O.sub.2206 2-phenylethyl " " A 168-170 C.sub.22 H.sub.21 ClN.sub.2 O.sub.2207 2-thienylmethyl " " A 189.5-190.5 C.sub.19 H.sub.17 ClN.sub.2 O.sub.2 S208 2-phenylethyl " 3-Cl A 200-203 C.sub.22 H.sub.20 Cl.sub.2 N.sub.2 O.sub.2209 2-phenylethyl Cl 6-Cl A 182-184.5 C.sub.22 H.sub.20 Cl.sub.2 N.sub.2 O.sub.2210 2-phenylethyl OCH.sub.3 H A 191-195 C.sub.23 H.sub.24 N.sub.2 O.sub.3211 butyl COOCH.sub.3 " A 132.8-134 C.sub.20 H.sub.24 N.sub.2 O.sub.4212 2-phenylethyl COOCH.sub.3 " A 159-161 C.sub.24 H.sub.24 N.sub.2 O.sub.4213 2-aminoethyl C.sub.2 H.sub.5 6-C.sub.2 H.sub.5 B oil C.sub.20 H.sub.27 N.sub.3 O.sub.2214 phenylmethyloxy Cl H A 174-175 C.sub.21 H.sub.19 ClN.sub.2 O.sub.3215 phenylmethyloxy C.sub.2 H.sub.5 6-C.sub.2 H.sub.5 A foam C.sub.25 H.sub.28 N.sub.2 O.sub.3216 methoxy C.sub.2 H.sub.5 6-C.sub.2 H.sub.5 A 126-127 C.sub.19 H.sub.24 N.sub.2 O.sub.3217 pentyloxy C.sub.2 H.sub.5 6-C.sub.2 H.sub.5 A oil C.sub.23 H.sub.32 N.sub.2 O.sub.3__________________________________________________________________________
TABLE 2__________________________________________________________________________ EvaluationEx. IR NMR Conc. Plant.No. .nu. value (cm.sup.-1) Method Chemical shift .delta. value Solvent (ppm) X Y Z__________________________________________________________________________1 1627, 1663 KBr 20 1 4 1 100 3 4 12 1630 " 2.28(6H), 2.42(3H), 2.90(3H), 6.40(1H, CDCl.sub.3 20 1 1 1 100 1 1 23 1625, 1655 " 2.24(3H), 2.43(3H), 2.81(3H), 6.42(1H, CDCl.sub.3 20 4 4 1 100 4 4 24 1600, 1650 " 2.17(6H), 2.25(3H), 2.65(3H), 6.20(1H, DMSO-d.sub.6 20 1 1 1 100 1 1 35 1600, 1637, 1653 " 2.22(3H), 2.27(3H), 2.71(3H), 6.20(1H, "-H) 20 1 1 3 100 1 1 56 1623, 1675 " 2.32(3H), 2.38(3H), 2.88(3H), 6.35(1H, CDCl.sub.3 20 2 3 3 100 3 4 47 1623, 1655 " 2.24(3H), 2.42(3H), 2.80(3H), 6.43(1H, "-H) 20 3 4 1 100 3 4 18 1623, 1657 " 2.20(3H), 2.39(3H), 2.77(3H), 6.41(1H, "-H) 20 4 4 1 100 4 4 19 1623, 1660 " 2.27(3H), 2.43(3H), 2.85(3H), 6.48(1H, "-H) 20 2 4 1 100 3 4 110 1630, 1665 " 2.24(3H), 2.41(3H), 2.81(3H), 6.45(1H, "-H) 20 4 3 1 100 4 4 311 1627, 1663 " 2.23(3H), 2.42(3H), 2.80(3H), 6.44(1H, "-H) 20 1 4 1 100 1 4 112 1607, 1630, 1665 " 2.25(3H), 2.41(3H), 2.80(3H), 3.72(3H), 6.40(1H, "-H) 20 4 4 1 100 4 4 113 1627, 1653 " 2.25(3H), 2.30(3H), 2.42(3H), 2.84(3H), 6.46(1H, "-H) 20 3 4 1 100 3 4 114 1607, 1657 " 2.22(3H), 2.29(3H), 2.40(3H), 2.80(3H), 6.41(1H, "-H) 20 4 3 2 100 4 3 215 1625, 1663 " 2.28(3H), 2.42(3H), 2.84(3H), 6.45(1H, "-H) 20 4 3 1 100 4 3 116 1627, 1663 " 1.27(9H), 2.29(3H), 2.42(3H), 2.83(3H), 6.43(1H, "-H) 20 1 1 1 100 2 2 117 1627, 1660 " 20 1 3 1 100 1 3 418 1625, 1657 " 20 3 4 1 100 3 4 119 1623, 1655 " 2.30(3H), 2.40(3H), 2.97(3H), 6.36(1H, "-H) 20 1 1 1 100 1 3 420 1617, 1665 " 2.34(3H), 2.90(3H), 6.37(1H, 5-H) " 20 1 3 3 100 1 3 421 2.25(3H), 2.81(3H), 6.44(1H, 5-H) " 20 1 3 1 100 3 4 522 1627, 1657 " 2.23(3H), 2.80(3H), 6.44(1H, 5-H) " 20 2 4 1 100 3 4 123 2.25(3H), 2.30(3H), 2.82(3H), 6.46(1H, " H) 20 2 4 1 100 3 4 124 1605, 1645 " 2.12(3H), 2.24(3H), 2.26(3H), 2.73(3H), 6.25(1H, "-H) 20 1 1 5 100 1 3 525 1607, 1630, 1663 " 2.27(6H), 2.36(3H), 2.90(3H), 6.35(1H, "-H) 20 1 3 4 100 3 4 426 2.26(3H), 2.30(6H), 2.81(3H), 6.45(1H, "-H) 20 4 4 1 100 4 4 327 2.22(3H), 2.30(6H), 2.80(3H), 6.45(1H, "-H) 20 1 3 1 100 1 3 128 1610, 1625, 1665 " 20 3 4 1 100 4 4 129 1617, 1647 " 2.23(3H), 2.28(6H), 2.78(3H), 6.42(1H, "-H) 20 4 4 1 100 4 4 130 1620, 1650 " 2.27(3H), 2.30(6H), 2.80(3H), 6.45(1H, "-H) 20 1 3 1 100 1 3 131 1615, 1665 " 2.27(3H), 2.28(6H), 2.82(3H), 6.47(1H, "-H) 20 1 4 1 100 1 4 132 2.24(3H), 2.30(6H), 2.80(3H), 6.47(1H, "-H) 20 1 1 1 100 1 2 133 1607, 1627, 1657 " 2.28(3H), 2.30(6H), 2.82(3H), 3.70(3H), 6.45(1H, "-H) 20 3 3 1 100 4 4 134 1625, 1655 " 2.27(3H), 2.29(6H), 2.82(3H), 3.74(3H), 6.43(1H, "-H) 20 4 4 1 100 4 4 135 1605, 1623, 1665 " 2.28(12H), 2.81(3H), 6.43(1H, 5-H) " 20 4 4 1 100 4 4 136 1623, 1653 " 2.25(3H), 2.28(9H), 2.81(3H), 6.42(1H, "-H) 20 4 4 1 100 4 4 137 1607, 1623, 1657 " 2.29(9H), 2.82(3H), 6.43(1H, 5-H) " 20 1 4 1 100 1 4 238 1623, 1667 " 1.27(9H), 2.29(9H), 2.83(3H), 6.45(1H, "-H)39 2.28(9H), 2.82(3H), 6.44(1H, 5-H) CDCl.sub.3 20 4 4 1 DMSO-d.sub.6 100 4 4 140 1627, 1657 " 2.24(3H), 2.31(6H), 2.88(3H), 6.31(1H, CDCl.sub.3 20 1 1 4 100 1 2 441 1617, 1650 " 2.27(6H), 2.39(3H), 2.83(3H), 6.44(1H, "-H) 20 1 3 1 100 1 4 142 1615, 1655 " 20 1 2 1 100 1 4 143 1617, 1665 " 20 1 3 1 100 2 3 144 1623, 1647 " 2.23(3H), 2.30(3H), 2.37(3H), 2.81(3H), 6.42(1H, "-H) 20 1 3 1 100 3 4 545 1617, 1655 " 2.24(6H), 2.36(3H), 2.86(3H), 6.37(1H, "-H) 20 1 2 4 100 2 4 346 1627, 1653 " 2.27(6H), 2.37(3H), 2.87(3H), 6.38(1H, "-H) 20 1 2 4 100 3 4 447 1625, 1655 " 2.27(6H), 2.35(3H), 2.83(3H), 6.42(1H, "-H) 20 1 1 3 100 1 2 448 1635, 1660 " 2.29(9H), 2.80(3H), 6.47(1H, 5-H) " 20 4 4 2 100 4 4 549 1627, 1657 " 2.23(3H), 2.27(6H), 2.76(3H), 6.45(1H, "-H) 20 1 4 1 100 4 4 150 1627, 1655 " 2.25(3H), 2.27(6H), 2.75(3H), 6.42(1H, "-H) 20 3 4 1 100 4 4 151 1635, 1667 " 2.27(9H), 2.75(3H), 6.42(1H, 5-H) " 20 3 4 2 100 3 4 452 1630, 1663 " 2.23(3H), 2.27(6H), 2.74(3H), 6.45(1H, "-H) 20 2 3 1 100 4 4 453 1625, 1663 " 2.26(9H), 2.76(3H), 6.44(1H, 5-H) " 20 2 4 1 100 4 4 154 1635, 1655 " 2.30(9H), 2.79(3H), 6.42(1H, 5-H) " 20 2 3 1 100 2 4 155 1600, 1627, 1660 " 2.28(6H), 2.33(3H), 2.92(3H), 6.40(1H, 20H) 4 5 4 100 5 5 456 1603, 1627 " 2.26(9H), 2.77(3H), 6.46(1H, 5-H) " 20 1 2 2 100 2 3 457 2.24(3H), 2.27(6H), 2.76(3H), 3.82(3H), 6.45(1H, "-H) 20 1 4 1 100 4 4 158 1603, 1625, 1650 " 2.29(9H), 2.80(3H), 3.74(3H), 6.45(1H, "-H) 20 2 4 1 100 4 4 159 1613, 1637, 1665 " 2.27(9H), 2.79(3H), 3.73(3H), 6.43(1H, CDCl.sub.3 20 3 3 1 DMSO-d.sub.6 100 4 3 160 1623, 1653 " 2.27(12H), 2.80(3H), 6.46(1H, 5-H) CDCl.sub.3 20 3 4 1 100 3 4 461 1600, 1637, 1665 " 2.26(12H), 2.78(3H), 6.42(1H, 5-H) " 20 4 4 1 100 4 4 362 1635, 1660 "63 1627, 1660 " 2.27(6H), 2.45(3H), 2.91(3H), 6.41(1H, "-H) 20 1 1 2 100 2 4 464 1625 " 2.24(6H), 2.30(3H), 2.78(3H), 6.44(1H, CDCl.sub.3 20 1 3 1 DMSO-d.sub.6 100 4 3 165 1627, 1655 " 2.28(3H), 2.34(3H), 2.93(3H), 6.36(1H, CDCl.sub.3 20 4 5 4 100 4 5 466 1617, 1657 " 2.26(3H), 2.37(3H), 2.87(3H), 6.38(1H, "-H) 20 1 2 2 100 2 3 467 1623, 1647 " 2.27(3H), 2.31(3H), 2.82(3H), 6.43(1H, "-H) 20 1 1 2 100 2 3 368 1625 " 2.26(6H), 2.79(3H), 6.47(1H, 5-H) " 20 2 2 3 100 2 3 569 1603, 1633 " 2.25(6H), 2.76(3H), 6.45(1H, 5-H) " 20 1 1 3 100 1 3 470 1627, 1660 " 2.24(6H), 2.76(3H), 6.45(1H, 5-H) " 20 2 4 3 100 3 4 571 1627 " 2.24(6H), 2.76(3H), 3.71(3H), 6.41(1H, "-H) 20 1 3 1 100 3 4 372 1630, 1650 " 2.28(6H), 2.34(3H), 2.79(3H), 6.47(1H, "-H) 20 2 3 1 100 4 4 473 1625, 1663 " 2.27(3H), 2.31(6H), 2.80(3H), 6.48(1H, CDCl.sub.3 20 1 4 1 DMSO-d.sub.6 100 3 4 474 1.96(3H), 2.60(3H), 6.28(1H, 5-H) CDCl.sub.3 20 1 2 1 100 1 2 475 1625, 1655 " 2.29(3H), 2.79(3H), 3.42(3H), 6.36(1H, "-H) 20 1 4 4 100 3 4 476 1615 " 2.38(3H), 2.88(3H), 6.40(1H, 5-H) " 20 1 2 3 100 1 3 477 1615, 1663 " 2.34(3H), 3.34(3H), 6.39(1H, 5-H) " 20 2 2 4 100 2 3 478 1623, 1655 " 2.38(3H), 2.88(3H), 6.40(1H, 5-H) " 20 1 4 3 100 4 4 379 1627, 1665 " 2.37(3H), 2.84(3H), 6.40(1H, 5-H) " 20 1 3 4 100 2 4 480 1623 " 2.37(3H), 2.87(3H), 6.39(1H, 5-H) " 20 4 4 4 100 5 4 481 1623, 1653 " 2.38(3H), 2.88(3H), 6.39(1H, 5-H) " 20 2 4 3 100 4 4 382 1627, 1655 Neat 2.39(3H), 2.87(3H), 6.40(1H, 5-H) " 20 4 4 4 100 5 4 483 1630, 1663 " 2.39(3H), 2.88(3H), 6.41(1H, 5-H) " 20 2 3 3 100 3 4 484 1627, 1660 " 2.35(3H), 2.84(3H), 6.39(1H, 5-H) " 20 1 5 3 100 4 5 485 1630, 1663 KBr 2.38(3H), 2.88(3H), 6.40(1H, 5-H) "86 1620 " 2.37(3H), 2.86(3H), 6.39(1H, 5-H) " 20 3 3 4 100 4 4 487 1623, 1645 " 2.31(3H), 2.80(3H), 6.41(1H, 5-H) " 20 2 3 3 100 2 4 488 1627, 1645 " 2.42(3H), 3.92(3H), 6.39(1H, 5-H) " 20 1 2 3 100 1 2 489 1615 " 2.28(3H), 2.78(3H), 6.48(1H, 5-H) " 20 1 3 5 100 1 4 590 2.25(3H), 2.78(3H), 6.49(1H, 5-H) " 20 1 2 4 100 4 3 491 2.28(3H), 2.79(3H), 6.49(1H, 5-H) " 20 1 4 2 100 1 4 492 2.25(3H), 2.76(3H), 6.49(1H, 5-H) " 20 2 3 3 100 3 4 493 2.27(3H), 2.76(3H), 6.47(1H, 5-H) " 20 2 4 2 100 4 5 494 1623 " 2.29(3H), 2.80(3H), 6.49(1H, 5-H) " 20 1 3 3 100 3 3 495 1625 " 2.27(3H), 2.77(3H), 6.45(1H, 5-H) " 20 1 4 4 100 3 4 496 1627 " 2.29(3H), 2.79(3H), 3.74(3H), 6.46(1H, "-H) 20 1 1 3 100 1 2 497 1627, 1647 " 2.29(3H), 2.79(3H), 3.73(3H), 6.45(1H, CDCl.sub.3 20 1 1 1 DMSO-d.sub.6 100 1 2 298 1625 " 2.27(3H), 2.31(3H), 2.78(3H), 6.48(1H, CDCl.sub.3 20 1 3 3 100 1 4 499 1620, 1650 " 2.28(3H), 2.31(3H), 2.79(3H), 6.47(1H, "-H) 20 2 2 1 100 2 4 1100 1625, 1653 " 2.45(3H), 2.92(3H), 6.43(1H, 5-H) " 20 1 2 4 100 2 2 4101 1627, 1653 " 2.31(3H), 2.80(3H), 6.47(1H, 5-H) " 20 1 1 2 100 2 2 4102 1627, 1657 " 2.39(3H), 2.85(3H), 6.36(1H, 5-H) " 20 1 3 3 100 2 4 3103 1625, 1657 Neat 2.32(3H), 2.90(3H), 6.40(1H, 5-H) " 20 4 4 4 100 5 4 4104 1617, 1663 KBr 2.44(3H), 2.88(3H), 6.37(1H, 5-H) CDCl.sub.3 20 1 1 1 DMSO-d.sub.6 100 1 2 2105 1627, 1655 Neat 2.40(3H), 2.87(3H), 3.29(3H), 6.40(1H, CDCl.sub.3 20 1 2 3 100 2 3 4106 1627 KBr 2.41(3H), 2.87(3H), 6.40(1H, 5-H) " 20 4 4 3 100 4 4 4107 1625, 1655 " 2.43(3H), 2.92(3H), 6.42(1H, 5-H) " 20 1 3 3 100 3 4 3108 1633 " 2.40(3H), 2.89(3H), 3.31(3H), 6.40(1H, "-H) 20 1 4 4 100 4 5 4109 1633, 1663 " 2.40(3H), 2.89(3H), 6.40(1H, 5-H) " 20 1 3 4 100 4 4 4110 1633, 1663 " 2.40(3H), 2.88(3H), 6.36(1H, 5-H) " 20 1 4 3 100 4 4 3111 1625, 1655 Neat 2.40(3H), 2.89(3H), 6.40(1H, 5-H) " 20 1 2 3 100 2 4 4112 1630, 1660 KBr 2.21(6H), 2.41(3H), 2.90(3H), 6.42(1H, "-H) 20 1 1 1 100 2 1 3113 1647 " 1.85(3H), 2.60(3H), 6.19(1H, 5-H) " 20 1 1 3 100 1 1 5114 1627 " 2.32(3H), 2.79(3H), 6.41(1H, 5-H) " 20 1 2 1 100 1 3 3115 1633, 1645 " 2.29(3H), 2.78(3H), 6.47(1H, 5-H) " 20 1 1 2 100 2 3 2116 1630, 1647 " 2.26(3H), 2.73(3H), 6.43(1H, 5-H) " 20 1 2 1 100 1 2 1117 1630, 1647 " 2.31(3H), 2.78(3H), 3.75(3H), 6.44(1H, CDCl.sub.3 20 1 1 1 DMSO-d.sub.6 100 1 1 2118 1630, 1647 " 2.30(6H), 2.77(3H), 6.47(1H, 5-H) CDCl.sub.3 + DMSO-d.sub.6119 1627, 1673 " 2.30(3H), 2.36(3H), 2.86(3H), 6.38(1H, CDCl.sub.3 20 1 2 4 100 1 3 4120 1627, 1663 " 2.33(6H), 2.91(3H), 6.36(1H, 5-H) " 20 1 4 4 100 2 4 4121 1627, 1657 " 2.27(3H), 2.39(3H), 2.84(3H), 6.46(1H, "-H) 20 1 3 1 100 1 4 2122 1627, 1670 " 2.25(3H), 2.38(3H), 2.81(3H), 6.43(1H, "-H) 20 1 2 1 100 1 2 1123 1647 " 2.27(3H), 2.77(3H), 6.23(1H, 5-H) CDCl.sub.3 + DMSO-d.sub.6124 1627, 1670 " 2.34(3H), 2.87(3H), 6.34(1H, 5-H) CDCl.sub.3 20 1 3 3 100 2 4 4125 1623, 1653 " 2.23(3H), 2.77(3H), 6.41(1H, 5-H) " 20 3 4 1 100 3 4 1126 1627, 1665 " 2.26(3H), 2.78(3H), 6.46(1H, 5-H) " 20 1 4 1 100 1 4 1127 1630, 1665 " 2.26(3H), 2.80(3H), 6.46(1H, 5-H) " 20 1 3 1 100 1 4 1128 1633, 1670 " 2.26(3H), 2.79(3H), 6.44(1H, 5-H) " 20 4 4 1 100 4 4 1129 1605, 1627, 1663 " 2.25(3H), 2.78(3H), 3.79(3H), 6.41(1H, "-H) 20 3 4 1 100 4 4 1130 1627, 1663 " 2.28(3H), 2.81(3H), 3.73(3H), 6.46(1H, "-H) 20 2 4 1 100 3 4 1131 1625, 1655 " 2.27(3H), 2.29(3H), 2.80(3H), 6.47(1H, "-H) 20 3 3 1 100 3 3 1132 1630, 1663 " 2.26(3H), 2.31(3H), 2.80(3H), 6.43(1H, "-H) 20 4 4 1 100 4 4 1133 1630, 1663 " 2.27(3H), 2.80(3H), 6.43(1H, 5-H) " 20 1 3 2 100 1 4 1134 1633, 1660 " 1.27(9H), 2.29(3H), 2.82(3H), 6.45(1H, "-H)135 1627, 1667 " 2.42(3H), 2.92(3H), 6.39(1H, 5-H) " 20 1 2 1 100 2 3 3136 1630, 1670 " 2.28(3H), 2.80(3H), 6.43(1H, 5-H) " 20 4 4 1 100 4 4 1137 1627, 1665 " 2.27(3H), 2.79(3H), 6.44(1H, 5-H) " 20 1 1 1 100 1 3 1138 1625, 1657 " 2.28(3H), 2.80(3H), 6.45(1H, 5-H) " 20 1 4 1 100 4 4 1139 1627, 1663 " 2.38(3H), 2.89(3H), 6.39(1H, 5-H) " 20 1 1 3 100 1 1 4140 1623, 1655 " 20 1 4 1 100 1 4 1141 1630, 1657 " 2.24(3H), 2.27(3H), 2.77(3H), 6.43(1H, "-H) 20 1 4 1 100 1 4 1142 1627, 1665 " 2.39(3H), 2.89(3H), 6.38(1H, 5-H) " 20 1 3 4 100 1 3 4143 1627, 1665 " 20 1 3 1 100 1 3 1144 1625, 1660 " 20 1 2 1 100 1 2 1145 1625, 1660 " 2.27(3H), 2.30(3H), 2.80(3H), 6.47(1H, "-H) 20 1 1 1 100 1 2 1146 1625, 1655 " 2.29(3H), 2.90(3H), 6.35(1H, 5-H) " 20 1 3 1 100 1 3 1147 1627, 1655 " 2.37(3H), 2.89(3H), 6.37(1H, 5-H) " 20 1 4 4 100 2 4 4148 1625, 1660 " 2.27(3H), 2.80(3H), 6.45(1H, 5-H) " 20 1 2 2 100 2 3 3149 1625, 1663 "150 1633, 1663 "151 1630, 1675 " 2.38(3H), 2.89(3H), 6.38(1H, 5-H) " 20 1 4 4 100 1 4 4152 1633, 1667 " 2.30(3H), 2.81(3H), 6.49(1H, 5-H) " 20 1 4 1 100 3 4 3153 1635, 1673 " 2.29(3H), 2.80(3H), 6.49(1H, 5-H) " 20 2 4 1 100 2 4 1154 1633, 1673 " 2.29(6H), 2.80(3H), 6.44(1H, 5-H) " 20 4 4 1 100 4 4 4155 1627, 1655 " 2.33(3H), 2.86(3H), 3.90(3H), 6.35(1H, "-H) 20 1 1 2 100 1 2 2156 1643 " 2.24(3H), 2.78(3H), 3.91(3H), 6.43(1H, "-H) 20 1 3 1 100 1 4 1157 1623, 1653 " 20 1 4 1 100 1 4 1158 1625, 1655 " 20 3 4 1 100 4 4 1159 1627, 1670 " 2.15(3H), 2.72(3H), 6.34(1H, 5-H) " 20 1 1 1 100 1 2 1160 1627, 1673 " 2.15(3H), 2.69(3H), 6.31(1H, 5-H) CDCl.sub.3 20 1 1 1 DMSO-d.sub.6 100 1 2 1161 1627, 1670 " 2.14(3H), 2.27(3H), 2.71(3H), 6.32(1H, CDCl.sub.3 20 1 1 1 100 1 2 1162 1605, 1630, 1673 " 2.27(3H), 2.36(3H), 6.27(1H, 5-H) DMSO-d.sub.6163 1650 " 2.22(3H), 2.37(3H), 6.16(1H, 5-H) CD.sub.3 OD164 1627 " 1.78(3H), 2.21(3H), 6.07(1H, 5-H) CDCl.sub.3 20 1 1 1 100 1 2 1165 1607, 1640, 1665, " 2.24(3H), 2.60(3H), 3.84(3H), 6.22(1H, CDCl.sub.3 20 1 1 5 1690, 1707 CD.sub.3 OD 100 1 1 5166 1600, 1620, 1643, " 2.24(3H), 2.53(3H), 3.87(3H), 6.39(1H, CDCl.sub.3 20 1 4 1 1703 100 2 4 1167 1605, 1627, 1667, " 20 1 4 1 1707 100 2 4 3168 1607, 1627, 1663, " 20 2 4 1 1700 100 3 4 1169 1617, 1675 " 2.35(3H), 2.40(3H), 2.91(3H), 6.36(1H, "-H) 20 3 4 4 100 4 4 4170 1625, 1675 " 2.35(3H), 2.39(3H), 2.90(3H), 6.34(1H, "-H) 20 4 4 3 100 4 4 3171 1627, 1667 " 2.40(6H), 2.92(3H), 6.36(1H, 5-H) " 20 1 4 2 100 3 4 2172 1615, 1673 " 2.34(3H), 2.68(3H), 2.71(3H), 5.71(1H, CD.sub.3 OD 20 4 4 1 100 4 4 1173 1625, 1653 " 2.29(3H), 2.40(3H), 2.83(3H), 6.43(1H, CDCl.sub.3 20 3 4 1 100 4 4 1174 1627, 1660 " 2.23(3H), 2.40(3H), 2.79(3H), 6.40(1H, "-H) 20 1 1 1 100 1 4 1175 1607, 1630, 1660 " 2.46(3H), 2.91(3H), 6.38(1H, 5-H) " 20 1 3 3 100 2 4 4176 1625, 1653 " 2.27(3H), 2.92(3H), 6.32(1H, 5-H) " 20 4 4 4 100 4 4 4177 1607, 1623, 1655 " 2.27(6H), 2.35(3H), 2.89(3H), 6.35(1H, "-H) 20 2 4 4 100 4 4 4178 1607, 1625, 1653 " 2.28(6H), 2.36(3H), 2.90(3H), 6.37(1H, "-H) 20 3 4 4 100 4 4 4179 1607, 1625, 1660 " 2.29(6H), 2.41(3H), 2.91(3H), 6.36(1H, "-H) 20 1 4 3 100 3 5 3180 1613, 1633, 1663 " 2.27(6H), 2.94(3H), 6.36(1H, 5-H) " 20 3 5 4 100 4 5 4181 1603, 1627, 1657 " 2.23(3H), 2.29(6H), 2.77(3H), 6.41(1H, "-H) 20 1 3 1 100 1 4 1182 1623, 1660 " 2.29(6H), 2.35(3H), 2.94(3H), 6.33(1H, "-H) 20 1 3 1 100 3 4 2183 1620, 1667 " 2.39(3H), 2.31(3H), 2.32(3H), CDCl.sub.3 20 1 2 4 2.91(3H), 6.34(1H, 5-H) DMSO-d.sub.6 100 1 2 4184 1637, 1665 " 2.34(6H), 2.97(3H), 6.34(1H, 5-H) CDCl.sub.3 20 4 4 4 100 5 4 4185 1617, 1657 " 2.28(6H), 2.39(3H), 2.89(3H), 6.38(1H, " H) 20 1 4 4 100 4 4 4186 1620, 1660 " 2.29(6H), 2.41(3H), 2.88(3H), 6.38(1H, "-H) 20 2 4 3 100 2 4 3187 1620, 1660 " 2.27(3H), 2.37(3H), 2.87(3H), 6.39(1H, "-H) 20 1 3 3 100 4 4 4188 1627, 1655 " 2.28(3H), 2.39(3H), 2.89(3H), 6.42(1H, "-H) 20 2 3 3 100 4 4 3189 1633 " 2.27(3H), 2.41(3H), 2.88(3H), 6.40(1H, "-H) 20 1 2 3 100 3 4 3190 1643 " 2.49(3H), 2.78(3H), 7.00(1H, 5-H) " 20 1 4 3 100 3 4 3191 1620, 1673 " 2.53(3H), 2.69(3H), 7.25(1H, 5-H) " 20 1 3 3 100 3 4 3192 1623 " 2.32(3H), 2.90(3H), 6.40(1H, 5-H) " 20 1 5 4 100 2 5 4193 1627 " 2.39(3H), 2.93(3H), 6.37(1H, 5-H) " 20 2 3 4 100 3 4 4194 1620 " 2.20(3H), 2.77(3H), 6.34(1H, 5-H) " 20 4 5 4 100 4 5 4195 1633, 1660 neat 2.28(3H), 2.80(3H), 6.34(1H, 5-H) " 20 2 4 4 100 4 4 4196 1627, 1643 KBr 2.36(3H), 2.86(3H), 6.41(1H, 5-H) " 20 1 1 3 100 3 3 3197 1627, 1655 " 2.01(3H), 2.95(3H), 6.41(1H, 5-H) " 20 1 2 4 100 2 3 4198 1607, 1617, 1657 " 2.27(3H), 2.45(3H), 2.81(3H), 6.45(1H, "-H) 20 4 4 4 100 4 4 4199 1627, 1657 " 2.30(3H), 2.32(3H), 2.49(3H), " 20 4 4 1 2.85(3H), 6.50(1H, 5-H) 100 4 4 1200 1603, 1623, 1670 " 2.39(3H), 2.45(3H), 2.92(3H), 6.39(1H, "-H) 20 1 4 4 100 1 4 4201 1600, 1623, 1660 " 2.32(3H), 2.46(3H), 2.98(3H), 6.40(1H, "-H) 20 4 5 4 100 4 5 4202 1630, 1657 " 2.29(3H), 2.35(3H), 2.96(3H), 6.32(1H, (1H, "-H) 20 1 4 4 100 1 4 4203 1625, 1665 " 2.29(6H), 2.90(3H), 6.36(1H, 5-H) " 20 4 5 4 100 4 5 4204 1633, 1673 " 2.37(3H), 2.89(3H), 6.37(1H, 5-H) " 20 1 4 4 100 1 4 4205 1627, 1675 " 2.35(3H), 2.88(3H), 6.35(1H, 5-H) " 20 1 4 1 100 1 4 1206 1637, 1667 " 2.29(3H), 2.90(3H), 6.33(1H, 5-H) " 20 4 5 4 100 4 5 4207 1627, 1673 " 2.39(3H), 2.91(3H), 6.43(1H, 5-H) " 20 2 4 1 100 3 4 3208 1630, 1663 " 2.31(3H), 2.90(3H), 6.36(1H, 5-H) " 20 2 3 3 100 4 3 3209 1625, 1670 " 2.35(3H), 2.97(3H), 6.44(1H, 5-H) " 20 1 2 4 100 1 3 4210 1600, 1627, 1663 " 2.27(3H), 2.90(3H), 3.85(3H), 6.32(1H, "-H) 20 1 1 1 100 1 4 4211 1610, 1633, 1677 " 2.32(3H), 2.61(3H), 3.85(3H), 6.29(1H, "-H) 20 1 1 3 100 1 2 4212 1607, 1635, 1660 " 2.27(3H), 2.61(3H), 3.83(3H), 6.27(1H, "-H) 20 1 1 1 100 2 4 4213 1625, 1650 neat 2.40(3H), 2.85(3H), 6.35(1H, 5-H) " 20 100214 1630, 1660 KBr 2.37(3H), 2.99(3H), 6.31(1H, 5-H) " 20 1 1 2 100 1 2 2215 1628, 1665 " 2.40(3H), 2.97(3H), 6.33(1H, 5-H) " 20 4 5 4 100 5 5 4216 1625, 1652 " 2.39(3H), 2.92(3H), 3.91(3H), 6.32(1H, "-H) 20 2 3 4 100 3 4 5217 1627, 1663 neat 2.39(3H), 2.90(3H), 6.34(1H, 5-H) " 20 4 4 4 100 4 4 4__________________________________________________________________________ X: Oryza sativa L. Y: Echinochloa crusgalli L. Z: Raphanus sativus L.

Number	Date	Country	Kind
59-223688	Oct 1984	JPX
60-2719	Jan 1985	JPX

4-oxo pyridinecarboxamide derivatives as plant growth regulators

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