JPH02247168A - 3-pyridinecarboxamide derivative, production thereof and plant growth inhibitor - Google Patents

Abstract

NEW MATERIAL:A 3-pyridinecarboxamide derivative expressed by formula I [R<1> and R<2> are 1-11C alkyl, lower alkenyl, lower alkynyl or aryl; R<3> is H, halogen, lower alkyl, lower alkenyl, lower alkynyl or aryl; R<4> is H, alkyl or alkenyl or R<2> and R<3> together form -(CH2)m- (m is 3 or 4); R<5> and R<6> are H or lower alkyl; R<7> is aryl]. EXAMPLE:2-Butyl-1,4-dihydro-1,5,6-trimethyl-N-(2-methyl-1-phenyl-1-pro penyl)-4- oxo-3-pyridinecarboxamide. USE:Capable of exhibiting growth inhibitory action on plants and anti- inflammatory action and useful as an agricultural chemical. PREPARATION:A compound expressed by formula II is reacted with a compound expressed by formula III in an insert solvent, preferably at ambient temperature to afford the compound expressed by formula I.

Description

DETAILED DESCRIPTION OF THE INVENTION (Industrial Field of Application) The present invention relates to novel compounds belonging to pyridine-3-carboxamides and methods for producing them. This compound exhibits a growth-inhibiting effect on plants and also has an anti-inflammatory effect.

(Prior art and problems to be solved by the invention) Conventionally,
Descriptions of compounds belonging to 1,4-dihydro-4-oxo-3-pyridinecarboxamide derivatives can be found in the following documents. Zankowska Ja-sins force, double, (Zankowska Ja-sins
ka, W, ) etc. [Bull, Acad, Po1
．． Sci, Ser, Sci.

Chim, 23(I1), 901(I975)], [Z
esz, Nauk, Uniw.

Jagiellon, Pr. Chim, 21.
141 (I976)]. Tetsu Kato Third Class [Pharmacy Journal, 10
1.40 (January I98. Also, Canadian patent m1.z
No. 15,278 [and J. B. Pierce et al. J.
Med, Chim.

25, 131 (I982)] describes 4-pyridone compounds with anti-inflammatory action. JP-A-6 = 54-24892, JP-A-51-43783, JP-A-5
No. 1-48686 discloses cephalosporins having a partial structure of 1,4-dihydro-4-oxo-3-pyridinecarboxamide for pharmaceutical use. on the other hand,
Derivatives of 1,4-dihydro-4-oxo-3-pyridinecarboxylic acid are known as compounds that exhibit activity as plant growth regulators, particularly as chemical hybridization agents (Japanese Patent Laid-Open No. 1983-1993).
144676, JP-A-57-114573). 1,4-dihydro-4-oxo-3, which also exhibits plant growth inhibitory effects.
-Pyridine carboxamide compounds are also known (JP-A-61-100567, JP-A-61-280478, JP-A-62-249972, JP-A-62-240664,
JP-A-63-45259, etc.).

However, 1,4- such as compound (I) of the present invention
A dihydro-4-oxo-3-pyridinecarboxamide compound and a plant growth inhibitor containing the same as an active ingredient have not been known so far.

The present invention provides a novel compound belonging to the 1,4-dihydro-4-oxo-3-pyridinecarboxamide compound, a method for producing the same, and a plant growth inhibitor containing at least one of these compounds as an active ingredient. It is.

(Means for Solving the Problems) The present inventors have completed the present invention as a result of intensive research to obtain the above-mentioned 1,4-dihydro-4-oxopyridine-3-carboxamide derivatives. That is, the present invention provides general formula (I): [wherein R1 and R2 may be different or the same, and each is an alkyl group, a lower alkenyl group, a lower alkynyl group, or an aryl group of 01 to C1, R3 is a hydrogen atom,
A halogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, or an aryl group; or R2 and R3 are
- together (-〇H2) m- (m is 3 or 4); R
4 represents a hydrogen atom, an alkyl group or an alkenyl group, R5 and R6 may be different or the same, each represents a hydrogen atom or a lower alkyl group, and R7 represents an aryl group. It is.

In this invention, the alkyl group includes linear or branched alkyl groups such as methyl, ethyl, propyl, butyl, isobutyl, pentyl, impentyl, hexyl, and octyl. Alkenyl groups include vinyl, allyl, impropenyl, 2-butenyl, 1,3-butadienyl,
2-pentenyl, 1,4-pentagenyl, 1,6-hebutagenyl, 1-hexenyl, etc., and alkynyl groups include ethynyl, 2-provinyl, etc. still,
In this invention, lower means a group containing 01 to C5 carbon atoms.

The aryl group includes a phenyl group; a phenyl group substituted with one or more of a halogen atom, a lower alkyl group, a lower alkoxy group, a cyan group, a nitro group, and a halogenated lower alkyl group.

Halogen atoms include chlorine, bromine, iodine, or fluorine atoms.

Specific examples of the compound represented by formula (I) include the following compounds.

2-Butyl-1,4-dihydro-1,5,6-trimethyl-N-(2-methyl-1-phenyl-1-propenyl)-4-oxo-3-pyridinecarboxamide 1,4-dihydro-1,6 -Simethyl-N-(2-methyl-1-tuunyl-1-butenyl)-4-ox,so2
-Propyl-3-pyridinecarboxamide 1,4-dihydro-N-(2-ethyl-1-phenyl-
1-Butenyl)-1,6-dimethyl-4-oxo-2-
Propyl-3-pyridinecarboxamide 5-allyl-1,4-dihydro-2,6-cymethyl-N
-(2-methyl-1-phenyl-1-propenyl)-4
-oxo-3-pyridinecarboxamide 5-allyl-1,4-dihydro-2,6-simethyl-N
-(2-Methyl-IJenyl-1-butenyl)-4-oxo-3-pyridinecarboxamide 5-allyl-N-(2-ethyl-1-phenyl-1-butenyl)-1, dihydro-2,6- Dimethyl-4-oxo-3-pyridinecarboxamide 5-bromo-1,4-dihydro-1,6-cymethyl-N
-(2-methyl-1-phenyl-1-propenyl)-4
-oxo-2-propyl-3-pyridinecarboxamide 5-bromo-1,4-dihydro-1,6-simethyl-N
-(2-methyl-1-phenyl-1-butenyl)-4-
Oxo-2-propyl-3-pyridinecarboxamide 5-bromo-N-(2-ethyl-1-phenyl-1-butenyl)-1,4-dihydro-1,6-simethyl-4-
Oxo-2-propyl-3-pyridinecarboxamide 5-bromo-1,4-dihydro-1,6-dimethyl-4
-oxo-N-(I-phenylethynyl)-2-furopyru-3-pyridinecarboxamide 5-bromo-1,4-dihydro-1,6-cymethyl-4
-OxoN-(I-phenyl-1-propenyl)-2-
Propyl-3-pyridinecarboxamide 5-bromo-1,4-dihydro-1,6-cymethyl-4
-oxo-N-(I-phenyl-1-butenyl)-2-
Propyl-3-pyridinecarboxamide 1-allyl-5-bromo-1,4-dihydro-6-methyl-N-(2-methyl-1-phenyl-1-propenyl)-4-oxo-2-propyl-3- Pyridinecarboxamide 5-bromo-2-hexyl-1,4-dihydro-1,6
-Simethyl-N-(2-methyl-1-phenyl-1-propenyl)-4-oxo-3-pyridinecarboxamide 5-bromo-1,4-dihydro-6-methyl-N-(2
-Methyl-1-phenyl-1-propenyl)-4-oxo-1゛,2-dipropyl-3-pyridinecarboxamide 5-bromo-1,4-dihydro-1,6-dimethyl-N
-(2-Methyl-1-p-chlorophenyl-1-propenyl)-4,oxo-2-brobyl-3-pyridinecarboxamide 1,4-dihydro-1,6-simethyl-N-
(2-methyl-1-phenyl-1-propenyl)-4-
Oxo-2,5-dipropyl-3-pyridinecarboxamide 5-bromo-1,4-dihydro-1,6-simethyl-N
-(2-methyl-1-p-tolyl-1-propenyl)-
4-oxo-2-propyl-3-pyridinecarboxamide 5-ethyl-1,4-dihydro-1,6-simethyl-N
-(2-methyl-1-phenyl-1-propenyl)-4
-oxo-2-propyl-3-pyridinecarboxamide 5-bromo-1,4-dihydro-1,2-dimethyl-N
=(2-methyl-1-phenyl-1-propenyl)-4
-Oxo-6-broby-3-pyridinecarboxamide 1.4,5,6,7.8-hexahydro-1-methyl-
N-(2-methyl-IJenyl-1-propenyl)-4
-Oxo-2-propyl-3-quinolinecarboxamide 4.5,6.7-tetrahydro-1-methyl-N-(2
-Methyl-1-phenyl-1-propenyl)-4-oxo-2-propyl-IH-1-pyrindine-3-carboxamide 5-chloro-1,4-dihydro-1,6-dimethyl-N
-(2-methyl-1-phenyl-1-propenyl)-4
-oxo-3-pyridinecarboxamide 2-butyl-1,4,5,6,7,8-hexahydro-
1-Methyl-N-(2-methyl-1-phenyl-1-propenyl)-4-oxo-3-quinolinecarboxamide 2-butyl-4,5,6,7-tetrahydro-1-methyl-N-(2 -Methyl-1-phenyl-1-propenyl)-4-oxo-IH-1-pyridine-3-carboxamide The 3-pyridinecarboxamide derivative of this invention can be produced by the following method.

That is, general formula (II): [wherein R1 and R2 may be different or the same, and each is a C1 to C1□ alkyl group, lower alkenyl group, lower alkynyl group, or aryl group; R3 is a hydrogen atom, A halogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, or an aryl group; or R2 and R3 are -
Together (-CH2) m- (m is 3 or 4); R5
and R6 may be different or the same, each represents a hydrogen atom or a lower alkyl group, and R7 represents an aryl group] and the compound represented by the general formula (III) -113= R4NH2 (III) [wherein R4 is a hydrogen atom , an alkyl group, or (represents an alkenyl group), the general formula (I) [wherein R1, R2, 1g%3.[4,[5,R6,H
(7) The 3-pyridine carboxamide derivative shown in the above example can be obtained.

In the production method of this invention, the formula (I
The compound I) means a compound that can be synthesized by the route shown below.

[In the formula, R1, R2, R3, R4, R5,, 16, R7 are the same as above, R8 is an alkyl group, N, N-dialkylamino group, N, N-dialkylaminoalkyl group, 1-pyrrolidylalkyl group , or morpholinoalkyl group; R9
represents a lower alkyl group. However, compound (V) (V'
) and compound (IXXIX') are tautomers of each other. ] Specific examples of the compound represented by formula (II) include the following compounds.

2-Butyl-5,6-simethyl-N-(2-methyl-1
-phenyl-1-phlobenyl)-4-oxo-4H-pyran-3-carboxamidromethyl-N-(2-methyl-1-phenyl-1-butenyl)-4-oxo-2-propyl-4H-pyran-
3-carboxamide N-(2-ethyl-1-phenyl,
1-butenyl)-6-methyl 4-oxo-2-propyl-4H-pyran-3-carboxamide 5-allyl-2,
6-Simethyl-N-(2-methyl-IJ enyl-1-propenyl)-4-oxo-4H-pyran-3-carboxamide 5-allyl-2,6-simethyl-N-(2-methyl-I
J enyl-1-butenyl)-4-oxo-4H-pyran-3-lupoxamide 5-allyl-N-(2-ethyl-1-phenyl-1-butenyl)-2,6-cymethyl-4-oxo-4H-pyran -3-Carboxamide 5-bromo-6-methyl-N-(2-methyl-1-phenyl-1-propenyl)-4-oxo-2-propyl-
4H-pyran-3-carboxamide 5-bromo-6-methyl-N-(2-methyl-1-phenyl-1-butenyl)-4-oxo-2-propyl-4
H-pyran-3-carboxamide 5-bromo-N-(2-ethyl-1-phenyl-1-butenyl)-6-methyl-4-oxo-2-propyl-4
H-pyran-3-carboxamide 5-bromo-6-methyl-4-oxo-N-(I-phenylethynyl)-2-propyl-4H-pyran-3-carboxamide 5-bromo-6-methyl-4-oxo -N
-(I-phenyl-1-propenyl)-2-propyl-
4H-pyran-3-carboxamide 5-bromo-6-methyl-4-oxo-N-(I-phenyl-1-butenyl)-2-propyl-4H-pyran-
3-carboxamide 5-bromo-6-methyl-N-(2
-Methyl-1-phenyl-1-propenyl)-4-oxo-2-propyl-4H-pyran-3-carboxamide 5-bromo-2-hexyl-6-methyl-N-(2-methyl-1-phenyl -1-propenyl)-4-oxo-
4H-pyran-3-carboxamide 5-bromo-6-methyl-N-(2-methyl-1-p-
Chlorophenyl-1-propenyl)-4-oxo-2-
Propyl-4H-pyran-3-carboxamidromethyl-N-(2-methyl-1-phenyl-1-propenyl)-4-oxo-2,5-dipropyl-4H-
Pyran-3-carboxamide 5-bromo-6-methyl-N-(2-methyl-1-p-
) true 1-propenyl)-4-oxo-2-propyl-4H nobilan-3-carboxamide 5-ethyl-6-methyl-N-(2-methyl-1-phenyl-1-propenyl)-4-oxo2- Propyl-4
H-pyran-3-carboxamide 5-bromo-2-methyl-N-(2-methyl-1-phenyl-1-propenyl)-4-oxo-6-broby-4H-pyran-3-carboxamide 5.6,7 .8-tetrahydro-N-(2-methyl-1
-phenyl-1-propenyl)-4-oxo-2-propyl-4H-chromene-3-carboxamide 4.5,6.7-titrahydroN-(2-methyl-1
-phenyl-1-propenyl)-4-oxo-2-propyl-4H-cyclopenta[bl pyran-3-carboxamide 5-chloro-6-methyl-N-(2-methyl-1
-phenyl-1-propenyl)-4-oxo-4H-pyran-3-carboxamide 2-butyl-5,6,7,8
-tetrahydro-N-(2-methyl-1-phenyl-1
-propenyl)-4-oxo-4H-chromene-3-carboxamide 2-butyl-4,5,6,7-titrahydroN-(2
-Methyl-1-phenyl-1-propenyl)-4-oxy(7-4H-cyclopenta[b]pyran-3-carboxamide) The reaction between a compound of formula (II) and a compound of formula (III) is carried out in an inert solvent, e.g. It can be carried out in water, ethanol, methanol, toluene, methylene chloride, chloroform, or ether. Reaction; temperature is -20°C to 600C1
Preferably it is around room temperature. The compound of formula (m) is usually used in an amount equal to or more than the amount of the compound of formula (II).

In this method, the reaction rate can be increased by adding an inorganic or organic base. Inorganic or organic bases include sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium ethoxide,
Examples include sodium methoxide, triethylamine, and pyridine. In the case of relatively strong bases such as sodium hydroxide and sodium carbonate, the amount of base to be used is based on formula (II).
A catalytic amount is sufficient for the compound of formula (II), but when using a relatively weak base such as triethylamine, the compound of formula (II)
Good results can be obtained by using an excess amount, preferably 2 equivalents or more, relative to the compound.

Further, general formula (■): [wherein R1 and R2 may be different or the same, and each is an alkyl group, lower alkenyl group, lower alkynyl group, or aryl group of 01 to C1□; R3 is a hydrogen atom, a halogen atom, lower alkyl group, lower alkenyl group, lower alkynyl group, or aryl group; or R2 and R3 are -
Together (-CH2)m - (m is 3 or 4); R
4 is a hydrogen atom, an alkyl group, or a lower alkenyl group, and
: R' [In the formula, R5 and R6 may be different or the same, and each represents a hydrogen atom, a lower alkyl group, and R7 represents an aryl group.] By reacting a compound represented by the general formula = (I ) A 3-pyridinecarboxamide derivative represented by the following formula can be obtained.

General formula (IV) used as raw material in the method of this invention
The compound is a 1,4-dihydro-4-oxo-3-pyridinecarboxylic acid of the general formula: (XII) The compound (X
Also included in the invention is a method using a reaction mixture of II) and a halogenating agent.

Specific examples of the compound represented by formula (XII) include the following compounds.

2-Butyl-1,4-dihydro-1,5,6-)rifthyl-4-oxo-3-pyridinecarboxylic acid 1,4-dihydro-1,6-dimethyl-4-oxo-2
-Propyl-3-pyridinecarboxylic acid 5-allyl-1,4-dihydro-2,6-cymethyl-4
-oxo-3-pyridinecarboxylic acid 5-bromo-1,4-dihydro-1,6-cymethyl-4
-oxo-2-propyl-3-pyridinecarboxylic acid 1-
Allyl-5-bromo-1,4-dihydro-6-methyl-
4-oxo-2-propyl-3-pyridinecarboxylic acid 5
-Bromo-2-n-1,4-dihydro-1,6-dimethyl-4-oxo-3-pyridinecarboxylic acid 1,4-dihydro-1,6-dimethyl-4-oxo-2
,5-dipropyl-3-pyridinecarboxylic acid 5-ethyl-1,4-dihydro-1,6-simethyl-4
-oxo-2-propyl-3-pyridinecarboxylic acid 5-
Bromo-1,4-dihydro-1,2dimethyl-4-oxo-6-broby-3-pyridinecarboxylic acid 1,4,5,6,7.8-hexahydro-1-methyl-
4-oxo-2-propyl-3-quinolinecarboxylic acid 4.5,6.7-tetrahydro-1-methyl-4-oxo-2-propyl-IH-1-pyrindine-3-carboxylic acid 5-chloro-1 ,4-dihydro-1,6-dimethyl-4-oxo-3-pyridinecarboxylic acid 2-butyl-1,4,5,6,7,8-hexahydro-
2-Butyl-4,5,6,7-tetrahydro-1-methyl-4-oxo-IH-1-pyrindine-3-carboxylic acid This compound (IV, ) and (V) or (V') are halogenated solvents such as methylene chloride, chloroform, and 1,2-dichloroethane, and aromatic hydrocarbon solvents such as benzene, toluene, and xylene. Among these, halogen-based solvents are particularly preferred.

The amount of the compound represented by the general formula (V) or (v') to be used is equal to or more than the amount of the compound represented by the general formula (IV), and there is no significant effect even if it is used in an amount of 2 equivalents or more. .

The reaction is carried out in the range of 0°C to the boiling point of the solvent used, preferably in the range of O'C to 30°C.

The amount of the 31a organic base used in the above reaction is determined by the reaction formula (
Good results can be obtained when compound (■) is used in an amount equivalent to or more when it is not an addition salt, and when it is used in an amount of 2 equivalents or more when it is an addition salt, to the compound V) or (V'). There is no significant effect even if 2 equivalents or more and 4 equivalents or more are used, respectively. Third! J.J.
1. Organic bases include -aliphatic or aromatic tertiary bases;
amines and nitrogen-containing heterocyclic groups. Examples of aliphatic tertiary amines include triethylamine, tripropylamine, N,N-dimethylbenzylamine, N,N-
Aromatic tertiary groups such as dimethylcyclohexylamine, amines such as N,N-dimethylaniline, N,N-diethylaniline, N,N-dimethyl-〇-toluidine, nitrogen-containing clathral bases such as N, -Methylpyrrolidine, N-methylpiperidine, N,N'-dimethylpiperazine, N-methylmorpholine and the like.

Furthermore, the present invention provides a plant growth inhibitor containing at least one compound of formula (I) or an addition salt thereof as an active ingredient.

In the plant growth inhibitor of the present invention, the active ingredient compound shown in (I) above may be used as it is, but generally depending on the purpose of use, solid carriers, liquid carriers, surfactants,
It is mixed with other formulation auxiliaries and formulated into wettable powders, granules, emulsions, etc.

These preparations contain 10 to 10% of hydrating powders as active ingredients.
80%, 0.1-20% for granules, 10-50% for emulsions
% (all percentages are by weight).

Solid carriers used in formulations include fine powders or granules such as kaolin, bentonite, clays, talc, diatomaceous earth, gicrite, zeolite, pyrophyllite, synthetic hydrous silicon oxide, and calcium carbonate; liquid carriers Examples include aromatic hydrocarbons such as xylene and methylnaphthalene, alcohols such as ethanol, isopropanol, ethylene glycol, and methyl cellosolve, ketones such as acetone, isophorone, and cyclohexanone, vegetable oils such as soybean oil and cottonseed oil, and dimethyl Examples include formamide, dimethyl sulfoxide, acetonitrile, water, etc. emulsification, dispersion,
Surfactants used for the wet layer include polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxy, ethylene polyoxypropylene Nonionic surfactants such as birenbrosulfate polymers, alkyl sulfate salts, alkyl sulfonate salts,
Examples include anionic surfactants such as alkylaryl sulfonates and polyoxyethylene alkyl sulfate salts.

Formulation adjuvants include lignin sulfonates, alginates, polyacrylates, polyvinyl alcohol, vegetable gums, carboxymethyl cellulose (CMC), hydroxyethyl cellulose (HEC), and the like.

Irrigation agents and emulsions prepared as described above can be diluted with water, and the granules can be applied as they are by spraying on soil or foliage.

The plant growth inhibitor of the present invention can also be used in combination with a nematocide, a fungicide, a fertilizer, or a soil conditioner.

When the plant growth inhibitor of this invention is used for either soil treatment or foliage treatment, the application amount can be varied over a fairly wide range, but usually the amount of active ingredient per are is 0.1 to 1.
The amount is 200 g, preferably 1 to 100 g, and the application concentration is 1% to 80% in water diluents for water use agents and emulsions.

These application amounts and concentrations can be increased or decreased depending on the type of preparation, application location, method, timing, crop, degree of weed damage, weather conditions, etc. without being affected by the above range.

(Example) The present invention will be explained in more detail with the following examples.

Example 1 2-Butyl-1,4-dihydro-N-(2-methyl-1
-Phenyl-1-propenyl)-1,5,6-drimethyl-4-oxo-3-pyridinecarboxamide The reaction formula of this example is shown by the following formula.

2-Butyl-56-cymethyl-N-(2-methyl-IJ
To a solution of 0.66 g (I, 9 mmol) of enyl-1-flobenyl)-4-oxo-4H-pyran-3-carboxamide in ethanol (3.5 ml), 1.9 ml (24 mmol) of a 40% aqueous methylamine solution was added. It was left at room temperature day and night. After evaporating the solvent under reduced pressure, appropriate amounts of methylene chloride and saturated aqueous sodium bicarbonate were added to the residue, followed by extraction with methylene chloride. The organic layer was dried over anhydrous magnesium sulfate, and methylene chloride was distilled off under reduced pressure. When the obtained crude crystals are recrystallized with hexane l ethyl acetate (I/1), the compound is 0.4
g (60% yield) was obtained.

Example 2 1,4-dihydro-1,6-dimethyl-N-(2-methyl-1-phenyl-1-butenyl)-4-oxo-2-
propino3-carboxamidrowmethyl-N-(2-methyl-1-phenyl-1-butenyl)-4-oxo-2-propyl-4H-pyran-
To an ethanol solution of 1.6 g (4.7 mmol) of 3-carboxamide = 29, 3.7 ml (47.7 mmol) of a 40% aqueous methylamine solution was added.
mol) was added and left at room temperature day and night. After distilling off the solvent, add appropriate amounts of methylene chloride and saturated sodium bicarbonate solution to the residue.
Extracted with methylene chloride. The organic layer is dried over anhydrous magnesium sulfate, and methylene chloride is distilled off under reduced pressure. The obtained residue was purified using a column (silica gel: w200°, ethyl acetate, methanol-1071) to obtain 15 g (yield: 91%) of the above compound.

Example 3 N-(2-methyl-1-phenyl-1-butenyl)-1
,4-dihydro-1,6-dimethyl-4-oxo-2-
The same operation as in Example 2 was performed except that the substituent of the propyl-3-carboxamide raw material was changed.

Example 4 5-allyl-1,4-dihydro-2,6-cymethyl-N
-(2-methyl-1-phenyl-1-propenyl)-4
-Oxo-3-pyridinecarboxamide The reaction formula of this example is shown by the following formula.

5-allyl-2,6-simethyl-N-(2-methyl-I
Jenyl-1-propenyl)-4-oxo-4H-pyran-3-carboxamide 1.7 g (5.4 mmol
) in ethanol (I, 3 ml), 6.5 ml of 28% ammonia water and 1 N aqueous sodium hydroxide solution.
．． 7 ml was added and left at room temperature day and night. After distilling off the solvent, appropriate amounts of methylene chloride and saturated sodium bicarbonate solution were added, and extraction with methylene chloride was performed. The organic layer was dried over anhydrous magnesium sulfate, and methylene chloride was distilled off under reduced pressure. The obtained crude crystals were recrystallized from ethyl acetate to obtain 1.2 g (yield: 68%) of the compound listed above.

Examples 5 and 6 The same operation as in Example 4 was performed except that the substituents of the raw materials were changed.

Example 5 5-allyl-1,4-dihydro-2,6-cymethyl-N
-(2-methyl-1-phenyl-1-butenyl)-4-
Oxo-3-pyridinecarboxamide Example 6 5-allyl-N-(2-ethyl-1-phenyl-1-butenyl)-1,4-dihydro-2,6-simethyl-4-
Oxo-3-pyridine, carboxamide Example 7 5-bromo-1,4-dihydro-1,6-cymethyl-N
-(2-methyl-1-phenyl-1-propenyl)-4
-Oxo-2-propyl-3-pyridinecarboxamide The reaction formula of this example is shown by the following formula.

0.63 ml (8.7 mmol) of thionyl chloride was slowly added dropwise under water cooling. After stirring for another hour at the same temperature, 0.36 ml of triethylamine (2,
A methylene chloride (2 ml) solution of 260 mg (I, 8 mmol) of 2-methyl-1-phenyl-propylideneamine (I, 6 mmol) was slowly added dropwise. After returning to room temperature and stirring for an additional 5 hours, the reaction solution was transferred to a separating funnel and washed with Hoiwa sodium bicarbonate solution and water. After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the resulting residue was purified by column chromatography (silica gel: w200, solvent ethyl acetate l methanol 10/l) to obtain 290 g (yield 80%) of the compound mentioned above. Obtained.

Yield, melting point, IH-NMR of the compound obtained above
The results of lIR are shown in Table 2 and Table II.

(Left below) 5-bromo-1,4-dihydro-1,6-cymethyl-4
-oxo-2-propyl-3-pyridinecarboxylic acid 25
0 mg (0.87 mmol) in methylene chloride 5 m
The performance evaluation of the compound obtained in Test Example 1.2.8.7 is shown in Table II.
I show. However, the “performance evaluation parameters” are as follows.

Talc (50 parts by weight), bentonite (25 parts by weight),
A carrier was prepared by mixing Tsurupol-9047 (manufactured by Toho Chemical Co., Ltd., 2 parts by weight) and Tsurupol-5039 (manufactured by Toho Chemical Co., Ltd., 3 parts by weight). A 20% wettable powder was prepared by mixing 50 parts by weight of the test compound and 200 parts by weight of the carrier.

This irrigation agent was purely dispersed to obtain a hydration agent dispersion having a predetermined concentration. Separately, petri dishes containing germinated rice, Japanese millet, and Japanese radish seeds were prepared, the above-mentioned hydrating agent dispersion was added, and the seedlings were grown for 7 days in a constant temperature bed with lighting at 25°C, and the degree of growth was observed. How to display the results: 1=no effect, 2=25
% growth inhibitor, 3 = 50% growth inhibitor, 4 = 75% growth inhibitor, 5 - complete death.

Claims (1)

[Claims] 1. General formula (I): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) [In the formula, R^1 and R^2 may be different or the same,
Each of C_1 to C_1_1 is an alkyl group, lower alkenyl group, lower alkynyl group, or aryl group; R^3 is a hydrogen atom, halogen atom, lower alkyl group, lower alkenyl group, lower alkynyl group, or aryl group; R^4 is , hydrogen atom, alkyl group, or alkenyl group; or R^
2 and R^3 are together (-CH_2)_m- (m is 3 or 4); R^5 and R^6 may be different or the same, and each is a hydrogen atom or a lower alkyl group; R^7 is A 3-pyridine carboxamide derivative represented by the formula ``representing an aryl group''. 2. General formula (II): ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (II) [In the formula, R^1 and R^2 may be different or the same,
Each of C_1 to C_1_1 is an alkyl group, lower alkenyl group, lower alkynyl group, or aryl group; R^3 is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, or an aryl group; or R^
2 and R^3 are together (-CH_2)_m- (m is 3 or 4); R^5 and R^6 may be different or the same, and each is a hydrogen atom or a lower alkyl group; R^7 is aryl group] and the compound represented by the general formula (III): R^4NH_2(III) [wherein R^4 represents a hydrogen atom, an alkyl group, or an alkenyl group] are reacted. General formula (I) characterized by: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) [In the formula, R^1, R^2, R^3, R^4, R^5, R^
6, R^7 is the same as above] A method for producing a 3-pyridine carboxamide derivative. 3. General formula (IV): ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (IV) [In the formula, R^1 and R^2 may be different or the same,
Each of C_1 to C_1_1 is an alkyl group, lower alkenyl group, lower alkynyl group, or aryl group; R^3 is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, or an aryl group; or R^
2 and R^3 together represent a compound or an addition salt thereof (-CH_2)_m- (m is 3 or 4); R^4 is a hydrogen atom, an alkyl group, or an alkenyl group, and X is a halogen atom] In the presence of an organic tertiary base in an inert solvent, the general formula (V) or (V'): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(V) ') [In the formula, R^5 and R^6 may be different or the same,
A general formula (I) characterized by reacting a compound represented by a hydrogen atom or a lower alkyl group; R^7 represents an aryl group, respectively: ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) [Formula Medium R^1, R^2, R^3, R^4, R^5, R^
6, R^7 is the same as above] A method for producing a 3-pyridine carboxamide derivative. 4. General formula (I): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) [In the formula, R^1 and R^2 may be different or the same,
Each of C_1 to C_1_1 is an alkyl group, lower alkenyl group, lower alkynyl group, or aryl group; R^3 is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, or an aryl group; or R^
2 and R^3 are together (-CH_2)_m- (m is 3 or 4); R^4 is a hydrogen atom, an alkyl group, or a lower alkenyl group; R^5 and R^6 are the same even if different a hydrogen atom or a lower alkyl group; R^7 represents an aryl group] or an addition salt thereof, as an active ingredient.