JP2001261632A - Method for producing disubstituted nitroguanidine derivative - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a simple method for economicall producing a high quality disubstituted nitroguanidine derivative. SOLUTION: This method for producing the disubstituted nitroguanidine derivative represented by formula (2) (R1 is an aromatic or non-aromatic hydrocarbon ring which may be substituted, an aromatic or non-aromatic heterocyclic ring which may be substituted, H, or an alkyl or alkenyl which may be substituted; R2 is a 1 to 6C alkyl), characterized by reacting a trisubstituted triazine represented by formula (1) (R3 is a 1 to 6C alkyl) with ammonia in the presence of a reaction accelerator in an aliphatic halogenated hydrocarbon solvent.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a novel method for producing disubstituted nitroguanidines. More specifically, equation (1)

[0002]

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(Wherein R 1 is an optionally substituted aromatic or non-aromatic hydrocarbon ring, an optionally substituted aromatic or non-aromatic heterocyclic ring, a hydrogen atom, an optionally substituted An alkyl group, an alkenyl group, or an alkynyl group, and R2 and R3 each represent an alkyl group having 1 to 6 carbon atoms). And reacting with ammonia in a high yield.

[0004]

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(Wherein R1 and R2 represent the same substituents as described above), and a method for producing a disubstituted nitroguanidine derivative represented by the formula:

The method of the present invention is very effective in producing a compound used as an agricultural chemical (particularly an insecticide) or an intermediate thereof.

[0007]

BACKGROUND OF THE INVENTION It is well known that certain nitroguanidines are useful as pesticides (especially insecticides) or their intermediates (JP-A-2-288860, JP-A-3-109374, JP-A-3-157308, JP-A-7-179448, etc.).

The compound of the formula (1) wherein R1 is a 3-tetrahydrofuryl group is disclosed in JP-A-7-17315.
7, JP-A-7-179448, JP-A-11-179448
It is manufactured by a method described in, for example, -236381.

In the method for producing disubstituted nitroguanidines described in JP-A-11-236381,
The desired product is produced by reacting 3,5-trisubstituted-2-nitroiminohexahydrotriazine with ammonia, a primary or secondary amine, and a salt thereof under non-aqueous conditions. In the above patent, the reaction can be carried out without solvent and under solvent dilution.
When decomposing 3,5-trisubstituted-2-nitroiminohexahydrotriazine to produce disubstituted nitroguanidines, an aliphatic halogenated hydrocarbon solvent is used in consideration of purification operations such as washing and crystallization. It is preferred to use
However, when an aliphatic halogenated hydrocarbon solvent is used as a solvent, high pressure reaction conditions with nitrogen as shown in Comparative Examples 1, 2, and 3 and reaction conditions at a high temperature are not high. The desired product could not be obtained in a yield.

When the reaction is carried out under the conditions of pressurized reaction with nitrogen and reaction conditions at a high temperature, the aliphatic halogenated hydrocarbon solvent as a solvent may be decomposed, or the resulting disubstituted nitroguanidine crystals may have a yellow color. -There was a problem that brownish coloring occurred and the quality of the product deteriorated.

[0011]

SUMMARY OF THE INVENTION In view of the above problems, an object of the present invention is to provide 1,3,5-trisubstituted-2 with ammonia in an aliphatic halogenated carbon-based solvent. An object of the present invention is to provide a production method capable of decomposing nitroiminohexahydrotriazine to obtain a high-quality disubstituted nitroguanidine economically.

[0012]

Means for Solving the Problems The present inventors have prepared 1,3,5-
As a result of intensive studies on a method for producing a disubstituted nitroguanidine by decomposing trisubstituted-2-nitroiminohexahydrotriazine, it was found that by adding a reaction aid, an economical and high-quality target product can be obtained. As a result, the present invention has been completed.

[0013] That is, the present invention includes the following items. Equation (1)

[0014]

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(Wherein, R 1 is an optionally substituted aromatic or non-aromatic hydrocarbon ring, an optionally substituted aromatic or non-aromatic heterocyclic ring, a hydrogen atom, an optionally substituted An alkyl group, an alkenyl group, or an alkynyl group, and R2 and R3 each represent an alkyl group having 1 to 6 carbon atoms). And reacting with ammonia

[0016]

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(Wherein R1 and R2 represent the same substituents as described above). The method described in Use of alcohol and / or water as reaction assistant. The method described in Use of Methanol as a Reaction Aid. In the above formulas (1) and (2), R1 is a pyridyl group, a thiazolyl group or a tetrahydrofuryl group which may be substituted. In the above formulas (1) and (2), R1 is 2-chloro-5
-The pyridyl group, the 2-chloro-5-thiazolyl group or the 3-tetrahydrofuryl group.

[0018]

DESCRIPTION OF THE PREFERRED EMBODIMENTS Typical examples of R1 in the above formulas (1) and (2) include a phenyl group, a 3-nitrophenyl group,
3-cyanophenyl group, 3-chlorophenyl group, 3-trifluoromethylphenyl group, cyclopentyl group, cyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 2-pyridyl group, 3-pyridyl group, 2-chloro -5-pyridyl group, 2-methoxypyridyl group, 5-thiazolyl group, 2-chloro-5-thiazolyl group, 2-methyl-5-thiazolyl group, 2-chloro-5-
Pyrimidyl group, 2-chloro-5-oxazolyl group, 3-
A furyl group, a 2-furyl group, a 3-tetrahydrofuryl group,
2-tetrahydrofuryl group, 2-methyl-4-tetrahydrofuryl group, 2-ethyl-4-tetrahydrofuryl group, 2-isopropyl-4-tetrahydrofuryl group, 2
-T-butyl-4-tetrahydrofuryl group, 2,2-dimethyl-4-tetrahydrofuryl group, hydrogen atom, methyl group, ethyl group, isopropyl group, t-butyl group, methoxymethyl group, methylthiomethyl group, chloromethyl Group, trifluoromethyl group, phenylmethyl group, vinyl group, ethynyl group and the like. Typical examples of R2 include a methyl group, an ethyl group, an n-propyl group, an allyl group, and a propargyl group. Typical examples of R3 include a methyl group, an ethyl group, an n-propyl group, an isopropyl group,
Examples include an n-butyl group and a cyclohexyl group.

The trisubstituted triazine represented by the formula (1) used in the present invention can be obtained by a method described in JP-A-7-179448 or the like. Specifically, a trisubstituted triazine can be obtained by alkylating a disubstituted triazine obtained by reacting a monosubstituted nitroguanidine with an aldehyde and an amine using an alkylating agent.

As the aliphatic halogenated hydrocarbon solvent, one having 1 to 2 carbon atoms is used. Examples thereof include dichloromethane, chloroform, carbon tetrachloride and 1,2-dichloroethane. Due to the solubility of the class, it is preferably dichloromethane.

Water and alcohols are used as reaction aids. Examples of alcohols used include methanol,
Ethanol, n-propyl alcohol, isopropyl alcohol, n-butanol and the like are mentioned, and methanol is preferable.

The amount of alcohol and water added to the reaction system as a reaction aid is at least 0.1 molar equivalent, preferably from 0.5 molar equivalent to trisubstituted nitroguanidine represented by the formula (1). 1.0 molar equivalent.

The amount of ammonia used is at least 0.1 molar equivalent, preferably at least 0.5 molar equivalent, based on the trisubstituted nitroguanidine represented by the formula (1).

The reaction temperature is 0 ° C. or higher, preferably 7 ° C.
0 ° C to 100 ° C.

The reaction time is generally from 0.1 hour to 7 days, preferably from 1 hour to 24 hours.

The post-treatment after the reaction can be carried out according to a conventional method. For example, after washing the reaction solution with water as needed, a crystallization operation can be performed to take out the target product. Further, if necessary, after removing salts by filtration or the like, the target substance can be taken out using silica gel column chromatography or the like. Purification such as water washing, activated carbon treatment, ion exchange resin treatment, recrystallization and the like can be performed as necessary to obtain a highly purified product.

The compounds having a nitroimino group represented by the formulas (1) and (2) can exist as syn- and anti-structural isomers and tautomers. In the case where R1 is a 3-tetrahydrofuryl group or the like in the formulas (1) and (2), an asymmetric carbon exists, and the compound may exist as an optically active substance, a racemic form, or a mixture at an arbitrary ratio. The present invention is also applicable to all isomers and tautomers of this type, and mixtures thereof in any proportion.

The method of the present invention is disclosed in JP-A-11-23638.
There are the following advantages as compared with the method for producing disubstituted nitroguanidine by decomposition of trisubstituted triazine using ammonia of the prior art shown in FIG. In the prior art, the amount of ammonia to be used is required to be 1 molar equivalent or more to the trisubstituted triazine, but in the present invention, a reaction yield of 97% or more can be obtained with 0.5 to 0.7 molar equivalent. it can. In the prior art, when an aliphatic halogenated carbon-based solvent is used, a reaction temperature of 100 ° C. or more is required,
When the reaction is carried out at a temperature of not more than ℃, it is necessary to pressurize the reaction system with nitrogen, and yellow-red-brown coloring is observed in the crystals of the disubstituted nitroguanidine obtained by crystallization purification, and the aliphatic halogenated carbon There was a problem that the solvent decomposed.
In the present invention, by using a reaction aid, even at a reaction temperature of 100 ° C. or less, there is no need to pressurize the reaction system with nitrogen,
Since the reaction is performed at a lower temperature, crystal coloring and solvent decomposition can be suppressed. When alcohol is used as a reaction aid, there is an effect of suppressing crystal coloring and an effect of suppressing solvent decomposition regardless of the reaction temperature.

The above can be confirmed in Example 1 and Comparative Example 1, as to Example 2 and Comparative Example 1, Comparative Example 2 and Comparative Example 3, and as to Example 3 and Comparative Example 2.

[0030]

EXAMPLES The present invention will be specifically described below with reference to examples and comparative examples. The reaction was performed in a pressurized system, and an autoclave made of SUS316 or Hastelloy was used as a reactor.

Example 1 1- (3-tetrahydrofuryl) methyl-3-methyl-
A solution of 5-isopropyl-2-nitroiminohexahydrotriazine (70.6 g) in dichloromethane (429)
g) with methanol (8.0 g), and after purging with nitrogen,
Ammonia (2.1 g) was added and reacted at 85 ° C. for 9 hours. The obtained reaction liquid (442 g) was used for 1- (3-tetrahydrofuryl) methyl-3-methyl-
It contained 48.1 g of 2-nitroguanidine (reaction yield 97.1%). The reaction solution was treated with 20% aqueous sulfuric acid (199 g).
, And re-extracted four times with dichloromethane (640 g) to obtain 2987 g of a dichloromethane solution containing 46.5 g of the desired product (extraction yield: 96.7%). The obtained dichloromethane solution was adjusted to a concentration of the target substance of about 35%.
Then, ethyl acetate (186 g) was added at 40 ° C., and the mixture was stirred for 2 hours. Thereafter, the crystallization mass was cooled to 5 ° C., and further stirred for 1 hour. After filtering the generated crystals,
After washing with ethyl acetate (74 g) and drying under reduced pressure, the target product was obtained as 44.8 g of white crystals (purity 9).
9.2%, crystallization yield 93.1%, process isolation yield 87.
4%). Solvent dichloromethane decomposition rate 1.0%. Table 1 shows the physical property values.

Example 2 1- (3-tetrahydrofuryl) methyl-3-methyl-
A solution of 5-isopropyl-2-nitroiminohexahydrotriazine (70.6 g) in dichloromethane (434)
g) with methanol (8.0 g), and after purging with nitrogen,
Ammonia (3.0 g) was added and reacted at 85 ° C. for 6 hours. The obtained reaction solution (438 g) was used for 1- (3-tetrahydrofuryl) methyl-3-methyl-
It contained 49.5 g of 2-nitroguanidine (reaction yield 98.4%). The reaction solution was treated with 20% aqueous sulfuric acid (197 g).
, And re-extracted four times with dichloromethane (657 g) to obtain 3087 g of a dichloromethane solution containing 48.1 g of the desired product (extraction yield: 96.7%). The obtained dichloromethane solution was concentrated until the concentration of the target substance became about 35%, ethyl acetate (192 g) was added at 40 ° C., and the mixture was stirred for 2 hours. Thereafter, the crystallization mass was cooled to 5 ° C., and further stirred for 1 hour. The resulting crystals were filtered, washed with ethyl acetate (77 g), and dried under reduced pressure.
The target product was obtained as 45.0 g of white crystals (purity: 99.0 g).
3%, crystallization yield 93.1%, process isolation yield 88.6
%). Solvent dichloromethane decomposition rate 0.9%. Table 1 shows the physical property values.

Example 3 1- (3-tetrahydrofuryl) methyl-3-methyl-
A solution of 5-isopropyl-2-nitroiminohexahydrotriazine (71.8 g) in dichloromethane (782)
g) and methanol (5.6 g), and after nitrogen replacement,
Ammonia (3.0 g) was added and reacted at 95 ° C. for 6 hours. The obtained reaction solution (785 g) was obtained using 1- (3-tetrahydrofuryl) methyl-3-methyl-
It contained 49.7 g of 2-nitroguanidine (reaction yield 97.6%). The reaction solution was treated with 20% aqueous sulfuric acid (353 g).
, And re-extracted four times with dichloromethane (1178 g) to obtain 5496 g of a dichloromethane solution containing 47.4 g of the desired product (extraction yield: 95.4%). The obtained dichloromethane solution was adjusted to a concentration of the target substance of about 35%.
Then, ethyl acetate (190 g) was added at 40 ° C., and the mixture was stirred for 2 hours. Thereafter, the crystallization mass was cooled to 5 ° C., and further stirred for 1 hour. After filtering the generated crystals,
After washing with ethyl acetate (76 g) and drying under reduced pressure, the target product was obtained as 43.7 g of white crystals (purity 9).
9.2%, crystallization yield 92.1%, process isolation yield 85.
8%). Solvent dichloromethane decomposition rate 1.7%. Table 1 shows the physical property values.

Example 4 1- (3-tetrahydrofuryl) methyl-3-methyl-
A solution of 5-isopropyl-2-nitroiminohexahydrotriazine (30.1 g) in dichloromethane (201
g) was mixed with water (1.9 g) and, after purging with nitrogen, ammonia (2.4 g) was added and reacted at 85 ° C. for 6 hours.
The obtained reaction solution (228 g) was obtained as the target product, 1- (3
-Tetrahydrofuryl) methyl-3-methyl-2-nitroguanidine in an amount of 20.1 g (reaction yield 9).
7.0%). The reaction solution was washed with 20% aqueous sulfuric acid (103 g) and re-extracted four times with dichloromethane (114 g) to obtain 674 g of a dichloromethane solution containing 19.6 g of the desired product (extraction yield: 97.4%). ). The obtained dichloromethane solution was concentrated until the concentration of the target substance became about 35%, ethyl acetate (80 g) was added at 40 ° C., and the mixture was stirred for 2 hours. Thereafter, the crystallization mass was cooled to 5 ° C., and further stirred for 1 hour. The resulting crystals were filtered, washed with ethyl acetate (32 g), and dried under reduced pressure to obtain 18.1 g of the desired product as white crystals (purity 99.0%, crystallization yield 92.3). %, Process isolation yield 87.2%). Solvent dichloromethane decomposition rate 1.8%. Table 1 shows the physical property values.

Example 5 1- (2-Chloro-5-pyridyl) methyl-3,5-dimethyl-2-nitroiminohexahydrotriazine 1
Methanol (1.5 g) was mixed with 5.0 g of a dichloromethane solution (150 g), and after purging with nitrogen, ammonia (0.6 g) was added and reacted at 85 ° C. for 6 hours. The obtained reaction solution (148 g) was used for the objective product, 1- (2-
It contained 11.1 g of chloro-5-pyridyl) methyl-3-methyl-2-nitroguanidine (reaction yield 9).
8.9%). The reaction solution was washed with 20% aqueous sulfuric acid (52 g), re-extracted three times with dichloromethane (74 g), and extracted with dichloromethane solution containing 10.8 g of the desired product.
57 g were obtained (extraction yield 97.4%). The obtained dichloromethane solution is concentrated until the concentration of the target substance reaches about 50%, and the formed crystals are filtered, washed with cooled dichloromethane (3 g), and dried under reduced pressure to obtain the target substance.
It was obtained as 8.1 g of white crystals (purity: 99.3%, crystallization yield: 87.8%, process isolation yield: 84.6%). Table 1 shows the physical property values.

Example 6 1- (2-chloro-5-thiazolyl) methyl-3,5-
Dimethyl-2-nitroiminohexahydrotriazine 1
Methanol (1.4 g) was mixed with 5.0 g of a dichloromethane solution (150 g), and after substitution with nitrogen, ammonia (0.6 g) was added and reacted at 85 ° C. for 8 hours. The obtained reaction solution (147 g) was obtained as 1- (2-
10.9 g of chloro-5-thiazolyl) methyl-3-methyl-2-nitroguanidine was contained (reaction yield 9).
7.0%). After the obtained reaction solution was concentrated under reduced pressure, ethyl acetate and water were added thereto, and the mixture was separated and washed. The obtained organic layer was dried under reduced pressure to isolate crystals, and then washed with cooled ethyl acetate. The crystals were dried under reduced pressure to give the desired product as 9.
It was obtained as 7 g of white crystals (purity 98.8%, crystallization yield 89.0%, process isolation yield 86.3%). Table 1 shows the physical property values.

Example 7 1- (3-tetrahydrofuryl) methyl-3-methyl-
Methanol (1.5 g) was mixed with a dichloromethane solution (100 g) of 5-methyl-2-nitroiminohexahydrotriazine (12.3 g), and after replacing with nitrogen, ammonia (0.6 g) was added. The reaction was performed for 6 hours.
The obtained reaction solution (98 g) was obtained as 1- (3-
It contained 9.5 g of (tetrahydrofuryl) methyl-3-methyl-2-nitroguanidine (reaction yield 97.9).
%). The reaction solution was washed with 20% aqueous sulfuric acid (45 g) and re-extracted four times with dichloromethane (50 g) to obtain 279 g of a dichloromethane solution containing 9.3 g of the desired product (extraction yield: 97.5%). ). The obtained dichloromethane solution was concentrated until the concentration of the target substance became about 35%, ethyl acetate (37 g) was added at 40 ° C., and the mixture was stirred for 2 hours.
Thereafter, the crystallization mass was cooled to 5 ° C., and further stirred for 1 hour. The resulting crystals were filtered, washed with ethyl acetate (14 g), and dried under reduced pressure to obtain 8.5 g of the target product as white crystals (purity: 99.5%, crystallization yield: 91.0%).
%, Process isolation yield 86.9%). Solvent dichloromethane decomposition rate 1.2%. Table 1 shows the physical property values.

Example 8 1- (3-tetrahydrofuryl) methyl-3-methyl-
A solution of 5-isopropyl-2-nitroiminohexahydrotriazine (61.2 g) in dichloromethane (483
g) with methanol (6.9 g), and after purging with nitrogen,
Ammonia (2.6 g) was added and reacted at 83 ° C. for 7 hours. The obtained reaction solution (488 g) was used for 1- (3-tetrahydrofuryl) methyl-3-methyl-
It contained 42.3 g of 2-nitroguanidine (reaction yield 97.6%). The reaction mixture was washed with 20% aqueous sulfuric acid (89 g) and re-extracted three times with dichloromethane (179 g) to obtain 960 g of a dichloromethane solution containing 41.3 g of the desired product (extraction yield: 97.6%). ). The obtained dichloromethane solution was concentrated until the concentration of the target substance became about 35%, ethyl acetate (165 g) was added at 40 ° C., and the mixture was stirred for 2 hours. Thereafter, the crystallization mass was cooled to 5 ° C., and further stirred for 1 hour. The resulting crystals were filtered, washed with ethyl acetate (66 g), and dried under reduced pressure.
The target product was obtained as 36.3 g of white crystals (purity 99.g).
1%, crystallization yield 87.9%, process isolation yield 83.7
%). Solvent dichloromethane decomposition rate 1.0%. Table 1 shows the physical property values.

Comparative Example 1 1- (3-tetrahydrofuryl) methyl-3-methyl-
A solution of 5-isopropyl-2-nitroiminohexahydrotriazine (32.1 g) in dichloromethane (243)
g) was replaced with nitrogen, and ammonia (1.9 g) was added.
The reaction was performed at 85 ° C. for 32 hours. The obtained reaction solution (233)
g) is the desired product, 1- (3-tetrahydrofuryl)
Methyl-3-methyl-2-nitroguanidine was added to 20.4
g (reaction yield: 89.8%). Reaction solution is 20
Aqueous solution (105 g) and dichloromethane (36
5g) for 4 times, and 19.8 g of the desired product was obtained.
1670 g of a dichloromethane solution was obtained (extraction yield: 97.3%). The obtained dichloromethane solution was concentrated until the concentration of the target substance became about 35%, and ethyl acetate (7%) was added.
9g) at 40 ° C. and stirred for 2 hours. Thereafter, the crystallization mass was cooled to 5 ° C., and further stirred for 1 hour. The resulting crystals were collected by filtration, washed with ethyl acetate (32 g), and dried under reduced pressure to obtain the desired product as 18.4 g of white crystals (purity: 98.7%, crystallization yield: 91.5%). %, Process isolation yield 79.9%). 1. Solvent dichloromethane decomposition rate
3%. Table 1 shows the physical property values.

Comparative Example 2 1- (3-tetrahydrofuryl) methyl-3-methyl-
5-Isopropyl-2-nitroiminohexahydrotriazine (15.0 g) in dichloromethane solution (150
g) was replaced with nitrogen, and ammonia (1.0 g) was added.
After pressurizing the inside of the reactor to 1.0 MPa with nitrogen, 90 ° C.
For 4 hours. The obtained reaction solution (145 g)
1- (3-Tetrahydrofuryl) methyl-
It contained 10.0 g of 3-methyl-2-nitroguanidine (reaction yield: 94.1%). The reaction solution was washed with 20% aqueous sulfuric acid (30 g) containing 5% sodium sulfate, and re-extracted three times with dichloromethane (65 g). The obtained dichloromethane solution was adjusted to a concentration of the target substance of about 35%. The mixture was concentrated until complete, ethyl acetate (39 g) was added at 40 ° C., and the mixture was stirred for 2 hours. Thereafter, the crystallization mass was cooled to 5 ° C., and further stirred for 1 hour. The resulting crystals were filtered, washed with ethyl acetate (16 g), and dried under reduced pressure.
The desired product was obtained as 8.8 g of slightly yellow crystals (purity 98.
3%, crystallization yield 88.2%, process isolation yield 83.0
%). Solvent dichloromethane decomposition rate 2.5%. Table 1 shows the physical property values.

Comparative Example 3 1- (3-tetrahydrofuryl) methyl-3-methyl-
5-isopropyl-2-nitroiminohexahydrotriazine (28.5 g) in dichloromethane (205
g) was replaced with nitrogen, and ammonia (1.4 g) was added.
The reaction was performed at 110 ° C. for 4 hours. The obtained reaction solution (200
g) is the desired product, 1- (3-tetrahydrofuryl)
9.5 g of methyl-3-methyl-2-nitroguanidine
Contained (reaction yield 96.5%). 20% reaction solution
Wash with aqueous sulfuric acid (90 g) and add dichloromethane (100
g) to obtain 611 g of a dichloromethane solution containing 8.8 g of the desired product (extraction yield 9).
2.4%). The obtained dichloromethane solution is concentrated until the concentration of the target substance becomes about 35%, and ethyl acetate (35 g) is obtained.
Was added at 40 ° C., and the mixture was stirred for 2 hours. Thereafter, the crystallization mass was cooled to 5 ° C., and further stirred for 1 hour. The resulting crystals were filtered, washed with ethyl acetate (14 g), and dried under reduced pressure to obtain 8.2 g of the desired product as yellow crystals (purity: 98.5%, crystallization yield: 93.6). %, Process isolation yield 83.5%). Solvent dichloromethane decomposition rate 4.9%.
Table 1 shows the physical property values.

[0042]

[Table 1]

[0043]

As described above, according to the method of the present invention, it is possible to produce a substituted nitroguanidine derivative useful as an agrochemical (particularly an insecticide) or an intermediate thereof by a simple method with high purity. Excellent as a manufacturing method.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) C07D 307/18 C07D 307/18 F-term (Reference) 4C033 AD10 AD18 4C037 DA03 4C055 AA01 BA02 BA39 CA06 CA11 CA27 CB01 CB10 DA01 4H006 AA02 AC59 AD15 AD17 BA28 BA29 BA50 BB12 BC10 BC19 BC31 4H011 AC01

Claims (5)

[Claims] (1) Formula (1) (Wherein, R 1 is an optionally substituted aromatic or non-aromatic hydrocarbon ring, an optionally substituted aromatic or non-aromatic heterocyclic ring, a hydrogen atom, an optionally substituted alkyl group or Represents an alkenyl group or an alkynyl group, R2, R3
Represents an alkyl group having 1 to 6 carbon atoms. Wherein a reaction aid is added to the trisubstituted triazine represented by the formula (1) in an aliphatic halogenated hydrocarbon solvent and reacted with ammonia. (Wherein, R1 and R2 represent the same substituents as described above). 2. The method according to claim 1, wherein an alcohol and / or water is used as a reaction assistant. 3. The method according to claim 1, wherein methanol is used as a reaction assistant. 4. The method according to claim 1, wherein in the formulas (1) and (2), R1 is an optionally substituted pyridyl group, thiazolyl group or tetrahydrofuryl group. 5. The method according to claim 1, wherein in the formulas (1) and (2), R1 is a 2-chloro-5-pyridyl group, a 2-chloro-5-thiazolyl group or a 3-tetrahydrofuryl group.