JPS62294669A - Triazine derivative, production thereof and herbicide containing said derivative as active ingredient - Google Patents

Abstract

NEW MATERIAL:A triazine derivative expressed by formula I (X<1>-X<3> are H, halogen, NO2, 1-4C haloalkyl, 1-4C haloalkoxy, 1-4C alkyl, 1-4C alkoxy or 1-4C alkylthio; R<1> is 1-4C alkyl; Y is halogen or 1-4C alkoxy). EXAMPLE:2-Chloro-4-amino-6-( 3-methyl-4'-methoxy-alpha-methylbenzylamino )-s-triazi ne. USE:A highly selective herbicide having high herbicidal effect on not only annual weeds but also perennial weeds without phytotoxicity to paddy rice. PREPARATION:A compound expressed by formula II is reacted with a compound expressed by formula III (Y<1> and Y<2> are halogen) to give a compound expressed by formula IV in formula I and the resultant compound is then reacted with a compound expressed by the formula R<2>OM1/n (R<2> is 1-4C alkyl; M is alkali metal or alkaline earth metal; n is the valence of M) to afford the aimed com pound expressed by formula I.

Description

[Detailed description of the invention] [Industrial application field] The present invention is a novel compound, a triazine derivative.

The present invention relates to a method for producing the same and a herbicide containing the same as an active ingredient.

[Prior art and problems to be solved by the invention] Various compounds have been known as triazine herbicides. For example, 2-methylthio-4,6-bis(
It is known that alkylamino)-s-) riazine derivatives have strong herbicidal power and are effective as herbicides.

However, for example 2-methylthio-4,6-bis(
The effectiveness of ethylamino)-S-) riazine is highly dependent on soil and temperature conditions. in particular,
In warm regions, even normal application rates may cause chemical damage, and in cold regions, there is a problem that the effect is not fully demonstrated. Therefore, it has the disadvantage that the areas where it can be applied as a herbicide are considerably restricted.

Therefore, 2-chloro-4,6-bis(alkylamino)-
Rice herbicides have been proposed in which the alkylamino group of s-triazine or 2-alkylthio-4,6-bis(alkylamino)-S-triazine derivatives is substituted with an α,α-dimethylbenzyl 7-mino group (especially Kimiaki/19-82
Publication No. 61, Special Publication No. 4, No. 9-8262). These compounds have no phytotoxic effects on paddy rice, and are effective against common weeds, but are extremely ineffective against perennial weeds, which are currently a problem.

[Problem that the invention seeks to solve]

The present inventors have solved the above-mentioned problems with conventional herbicides, and have demonstrated that they are almost equally effective under various soil and temperature conditions, are not harmful to paddy rice, and are effective against a variety of weeds ranging from annual to perennial weeds. We conducted extensive research in order to develop a completely new herbicide that would have an exceptional herbicide effect.

[Means for solving problems]

As a result, the inventors discovered that a specific triazine derivative was suitable for the above purpose, and completed the present invention.

That is, the present invention is based on the general formula [wherein, X I , X 2 , and It represents an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkylthio group having 1 to 4 carbon atoms, R' represents an alkyl group having 1 to 4 carbon atoms, and Y is a halogen atom or an alkyl group having 1 to 4 carbon atoms. Indicates 1 to 4 alkoxy groups. ] Provides a triazine derivative represented by the general formula [wherein x l, x2 . X:l and R1 are jrI
Same as above. ] A hensylamine derivative represented by the formula [In the formula, Y' and Y2 each represent a halogen atom. ]
A general formula characterized by reacting a dihalogenated aminotriazine represented by [wherein X I , X Z , X 3 , Y l
and R1 are the same as above. ] A method for producing a triazine derivative represented by (hereinafter referred to as "method-1") and a triazine derivative of the formula CIV'l, in which R20M, /, C, R2
represents an alkyl group having 1 to 4 carbon atoms, and M represents an alkali metal or an alkaline earth metal.

Further, n indicates the valence of M. A method for producing a triazine derivative represented by the general formula [wherein, X'+X''+X3+R' and R2 are the same as above] (hereinafter referred to as "Method-2"), characterized by reacting an alcoholade represented by ).

Furthermore, the present invention also provides a herbicide containing a triazine derivative represented by the above general formula [■] as an active ingredient.

The compound represented by the general formula CI) is a triazine derivative, where xl, X2. )<3. R1 and Y
is as described above. That is, X', X2°X3 are a hydrogen atom, a chlorine atom, and a bromine atom, respectively.

Halogen atoms such as fluorine atoms and iodine atoms, and nitro groups.

trifluoromethyl group, trichloromethyl group, trichloroethyl group, dichloroethyl group, monochloromethyl group,
A haloalkyl group having 1 to 4 carbon atoms such as a monobromomethyl group and a monofluoromethyl group.

Monochloromethoxy group, difluoromethoxy group.

Monochloroethoxy group, monofluoromethoxy group.

C1-C4 haloalkoxy groups such as trifluoromethoxy groups, C1-4 alkyl groups such as methyl, ethyl, isopropyl groups, methoxy groups, ethoxy groups,
It represents an alkoxy group having 1 to 4 carbon atoms, such as a normal propoxy group or an isopropoxy group, or an alkylthio group having 1 to 4 carbon atoms, such as a methylthio group, an ethylthio group, or a propylthio group. Further, R1 represents an alkyl group having 1 to 4 carbon atoms, such as a methyl group, ethyl group, propyl group, or butyl group, and Y represents a halogen atom, such as a chlorine atom, a bromine atom, an iodine atom, or a fluorine atom.

There are various specific examples of the triazine derivative of the present invention, but in addition to the compounds obtained in the production examples described below,
2-chloro-4-amino-6-(3'4'-dinormalpropoxy-α-methylbenzylamino)-s-1-riazine, 2-chloro-4-amino-6-(3'-methyl-4゛-Normal propoxy-α-methylbenzylamino)-3-1 riazine, 2-chloro-4-amino-6
-(3''-trifluoro-4'-nitro-α-methylhensylamino)-3-triazine, 2-chloror+-4-
Amino-6-(3'-trifluoro-4'-chloro-α
-methylbenzylamino)-3-) riazine 12-chloro-4-amino-6-(3'4''-diethyl-α-methylhensylamino) -S-triazine.

2-chloro-4-amino-6-(3',4"-dibromo-α-methylbenzylamino)-S-) riazine, 2-
Chloro-4-amino-6-(3'', 4'-difluoro-
α-methylhensylamino)-S-triazine, 2-chloro-4-amino-6-(3′-methyl-5′-methoxy-α-methylbenzylamino>-s−+-riazine,
2-chloro-4-amino-6-(3', 4°, 5'-
1-Rimemo-α-methylhensylamino)-S-triazine, 2-4-4-amino-6-(4'-methylthio-α-methylhensylamino)-S-triazine,
2-chloro-4-amino-6-(4°-methyl-α-methylhensylamino)-S-triazine, 2-chloro-
4-amino-6-(3'-chloro-α-methylhensylamino)-S-triazine, 2-chloro-4-amino-
6-(3″-methoxy-4″-methyl-α-ethylbenzylamino)-s-MJ azine, 2-chloro-4-amino-6-(3′,5°-dimethyl-α-ethylbenzylamino) -3-triazine, 2-chloro-4-amino-
6-(3゜-methyl-α-ethylbenzylamino)-S
-triazine, 2-chloro-4-amino-6-(α-ethylbenzylamino)-3-1-riazine, 2-methoxy-4-amino-6-(3'-methoxy-4”-methyl-α- methylbenzylamino)-S-triazine, 2
-Ethoxy-4-amino-6-(3'-methoxy-4'-methyl-α-methylhensylamino)-3-1 riazine, 2-methoxy-4-amino-6 (3' + 5'-
dimethyl-α-methylbenzylamino)-S-triazine, 2-ethoxy-4-amino-6-(3'-methyl-
Examples include α-methylhensylamino)-5-1-riazine.

The triazine derivative of the present invention represented by the above general formula (1) can be produced by various methods. Among these methods, the above-mentioned method 1 or method 2 is cited as a more efficient method.

According to method-1, a hensylamine derivative (t) represented by the -γ general formula [[1] and a dihalogenated aminotriazine represented by -fY2(lII) are reacted to form the desired general formula (TV ) (This corresponds to a part of the triazine derivative of -i(1). That is, the triazine derivative when Y in formula (1) is a halogen atom.) can get.

There are various benzylamine derivatives represented by the general formula (IT), that is, α-alkylbenzylamine derivatives. X'lX"lX in general formula (II)
' and R1 are as described above, specifically substituents (X', X'') corresponding to the type of triazine derivative of general formula [I] to be produced.

A benzylamine derivative having X', R') may be selected.

Although various methods can be considered for producing the hensylamine derivative represented by the above general formula (II), the following method is usually used.

That is, in the general formula C, x + , X 2 and X3 are the same as above. ] Substituted Hensen represented by the general formula R'COX [wherein,
X represents a halogen atom, and R1 is the same as above. ]
An acyl halide represented by the general formula [in the formula, X I , X 2. x3 and R1 are the same as above. ] A phenone derivative represented by is obtained, and then 150
Ammonium formate or formamide is reacted with formic acid under heating at about 200° C. to form a compound of the general formula [wherein, XI, XZ, X3 and R1 are the same as above. ] N-formylhensylamine RF represented by: Obtain a conductor. If this is further heated and hydrolyzed in the presence of an acid such as concentrated hydrochloric acid or a caustic alkali such as caustic soda,
Benzylamine derivative 3,7' represented by general formula (II)
5 bodies are obtained.

In addition, phenone 74t4 represented by the above general formula [■]
Oxime (phenone oxime derivative) is produced by reacting the B form with hydroxylamine instead of ammonium, and this is reduced with an alkali metal such as metal sulfurium in alcohol, or by catalytic reduction. A benzylamine derivative 4 represented by the desired general formula C11) is obtained.

Furthermore, the general formula [wherein, x l , x Z and X3 are the same as above]. ] The general formula R'Mg is added to the cyanohenzene derivative 4 represented by
A Grignard reagent represented by Conductors can be manufactured as follows.

In method-1 of the present invention, the hensylamine derivative represented by the general formula [■] thus obtained and the dihalogenated aminotriazine represented by the general formula (III), that is, 2,6-dihalogeno-4=amino- 5-React with 1-riazine. Here, dihalogenated aminotriazine is obtained by reacting ammonia with halogenated cyanuric acid such as dihalogenated aminotriazine or anuric acid chloride. Moreover, this hensylamine derivative of the general formula [111] and the general formula (II
In the reaction with the dihalogenated aminotriazine in I), the recompounds may be used in approximately equimolar ratios, and a solvent is not necessarily required, but methanol may be used.

Alcohols such as ethanol and isopropanol, ketones such as acetone, methyl ethyl ketone, and cyclohexanone, aliphatic hydrocarbons such as n-hexane and n-heptane, cyclic hydrocarbons such as benzene, decalin, and alkylnaphthalene, carbon tetrachloride, and tetrachloride. Chlorinated hydrocarbons such as ethylene, ethers such as tetrahydrofuran and dioxane, etc. can also be used. Furthermore, in this reaction system, hydrogen carbonate 1-
It is also effective to add a deoxidizing agent (dehydrohalogenating agent) such as triethylamine or triethylamine. In addition, the reaction temperature is not particularly limited to iil+, and can range from low to high temperatures, specifically from 10 to
It progresses satisfactorily in the range of 100°C.

According to method-1 of the present invention, the desired triazine derivative represented by the general formula (TV) is obtained by the above reaction.

On the other hand, according to method-2 of the present invention, the above general formula CrV)
The triazine derivative has the above-mentioned general formula R" OM l/
In formulas I and C, R'', M and n are the same as above.]
By reacting the alcoholade represented by is a triazine derivative when is an alkoxy group having 1 to 4 carbon atoms.) is obtained. The above Alcolade used here has the -C formula R"OM, /f
i, in which R2 is a methyl group, an ethyl group,
It represents an alkyl group having 1 to 4 carbon atoms such as a propyl group, and M represents an alkali metal such as sodium or potassium or an alkaline earth metal such as magnesium or calcium. Specifically, sodium methylate (CHzON a ), potassium methylate (CH30K).

Sodium ethylate (C2H, ○Na), potassium ethylate) (C2H50K), magnicium methylate ((CHiO)zMg), calcium methylate ((CH30)2Ca), magnesium ethylate <
(C2r-rso)zMg), calcium ethylate ((CzHsO)zCa), etc. can be mentioned.

Triazine HA of general formula [■] added during the above reaction
The ratio of the 'jL form and the above-mentioned Alcola-1 is not particularly limited, but may be equimolar. This reaction also uses methanol, ethanol, isopropyl alcohol, dimethylformamide, and toluene.

It also proceeds in solvents such as xylene and benzene. In addition, there is no particular uniform for reaction 4 changes, from low temperature to high temperature, specifically 1
It progresses satisfactorily in the range of 0 to 150°C.

After the reaction is completed, by separating and washing the product, the triazine λV form represented by the general formula [■] of the present invention can be obtained with high purity and high yield.

The triazine derivative of the present invention produced in this way (
General formula C1), represented by (rV] or [■])
is a novel compound and is effective in weed germination.

It is suitable as a herbicide because it inhibits growth and has high selectivity. In addition, it not only shows excellent herbicidal effects on weeds such as broad-leaved weeds such as Prunus japonicus, azalea, and Aspergillus japonica, Cyperaceae weeds such as Kumagayari, and Poaceae weeds such as Novie, but also has a current control effect. It also exhibits excellent weeding effects against perennial weeds such as firefly (Japanese firefly), Japanese turmeric (Japanese lily), and Japanese bush lily.

Next, the herbicide of the present invention is a compound of the above-mentioned invention, that is, general formula [I] (or (IV) or [■])
These compounds are mixed with a liquid carrier such as a refrigerant or a solid carrier such as ↑JΣ anastomotic fine powder, and are prepared as active ingredient, emulsion, emulsion, etc.
It can be formulated and used in the form of a single powder or the like. A surfactant may be added to impart emulsifying properties, dispersibility, spreading properties, etc. during formulation.

When the herbicide of the present invention is used in the form of a wettable powder, the above-mentioned triazide 2415 of the present invention is usually used as an active ingredient.
A composition may be prepared by blending 0 to 55% by weight of the solid carrier, 10 to 88% by weight of the solid carrier, and 2 to 5% by weight of the surfactant, and then used.

In addition, when used in the form of an emulsion, the triazine derivative of the present invention is usually used as an active ingredient in an amount of 20 to 50% by weight, and a solvent as a solvent.
It may be prepared by mixing 5 to 75% by weight of the surfactant and 5 to 15% by weight of the surfactant.

On the other hand, when used in powder form, if! Usually 1-15% by weight of the triazine derivative of the invention, 80-97% by weight of solid carrier and 2-5% by weight of surfactant as active ingredients.
It may be prepared by blending them in the following proportions.

Furthermore, when used in the form of granules, 1 to 15% by weight of the triazine derivative of the present invention as an active ingredient and 80% by weight as a solid carrier.
It may be prepared by blending the surfactant in a proportion of ~97% by weight and a surfactant in a proportion of 2 to 5 times the weight. Here, fine mineral powder is used as the solid carrier, and examples of the fine mineral powder include diatomaceous earth, oxides such as slaked lime, phosphates such as apatite, sulfates such as cypress, talc, and pyroferrite. ,clay,
Examples include silicates such as kaolin, bentonite, acid clay, white carbon, quartz powder, and silica powder.

In addition, organic solvents are used as solvents, specifically aromatic hydrocarbons such as xylene, toluene, betaine, etc.
Chlorinated hydrocarbons such as chlorotoluene, trichloromethane, and trichlorethylene; alcohols such as cyclohexanol, amyl alcohol, and ethylene glycol; ketones such as isophorone, cyclohexanone, and cyclohexenyl-cyclohexanone; and ethers such as butyl cellosolve, dimethyl ether, and methyl ethyl ether. , esters such as isopropyl acetate, hensyl acetate, methyl phthalate,
Amides such as dimethylformamide or mixtures thereof can be mentioned.

Further, as the surfactant, any of anionic, nonionic, cationic, and amphoteric ionic types (amino acids, betaine, etc.) can be used.

〔Effect of the invention〕

The triazine HA ff1 body of the novel compound represented by the general formula [■] of the present invention has the following properties: (It has a high herbicidal effect on not only grasses but also perennial weeds, and is extremely useful as a highly selective herbicide with no chemical damage to paddy rice.

The herbicide of the present invention has general formula (1) as an active ingredient.
Other herbicidal ingredients can also be used together with the triazine derivative represented by. Examples of such other herbicidal ingredients include conventionally commercially available herbicides, such as phenoxy herbicides, diphenyl ether herbicides, triazine herbicides, urea herbicides, carbamate herbicides, Various herbicides include thiol carbamate herbicides, acid anilide herbicides, viradul herbicides, phosphoric acid herbicides, and oxacycin.

Furthermore, the herbicide of the present invention can be used as an insecticide depending on the situation.

It can also be used in combination with fungicides, plant growth regulators, fertilizers, etc.

The herbicide of the present invention is characterized by having greater medicinal efficacy, less phytotoxicity, and a wider herbicidal spectrum width than existing herbicides for paddy rice.

Specifically, it is highly effective against wildflowers and broad-leaved weeds, and
It shows remarkable effects on perennial weeds such as lily and cypress.

(Examples) Next, the present invention will be explained in more detail with reference to Examples and Comparative Examples.

Reference example 1 (Synthesis of hensylamine derivative) Water 110m
7! 81.5 g of sodium hydroxide (2,0, i
34.0 g (227 mmol) of 3-methyl-4-hydroxyacetophenone and 1,
After adding 190 ml of 4-dioxane and raising the temperature to 70-80°C, 1 ml of Freon-22 (CtlF, Cl2) gas was added.
Introduced time. After cooling, the mixture was diluted with 1000 m6 of water and extracted with 500 m1 of ethyl ether.

The ethyl ether layer was dried with sodium sulfate, and the ethyl ether was distilled off under reduced pressure to obtain 43.4 g of oily 3-methyl-4-difluoromethoxy-acetophenone (yield: 9
6%).

22.0 g (110 mmol) of this 3-methyl-4-difluoromethoxyacetophenone and 2 ammonium formate
5.2 g (400 mmol) were stirred at 180°C for 5 hours.

The reaction mixture was mixed with benzene 200+++j! dissolved in
After washing with water and drying 1-lium sulfate, benzene was distilled off under reduced pressure. A 5% sodium hydroxide solution (20 On+j2) was added to the product after benzene was distilled off, and the mixture was stirred at 70°C for 7 hours.

After cooling, 200 mj2 of ethyl ether was added and the organic layer was separated. After drying this organic layer over sodium sulfate, ethyl ether was distilled off under reduced pressure, and 3.80 g of 3-methyl-4-difluoromethoxy-α-methylbenzylamine, a hensylamine derivative represented by the following formula (yield: 1
5%).

2 (Reference Example 2 (Synthesis of hensylamine derivative) 36.5 g (214 mmol) of 2-chloroethoxytoluene and 20.5 g (262 mmol) of acetyl chloride were dissolved in 250 mf of methylene chloride, and the mixture was cooled on ice. While stirring, 34.7 g (260 mmol) of aluminum chloride was gradually added, followed by stirring for 20 minutes under water cooling.Then, the reaction mixture was added to 1200 mf of 5% hydrochloric acid, and separated into an aqueous layer and an organic layer. The obtained organic layer was washed with a 5% aqueous sodium carbonate solution, dried over sodium sulfate, and methylene chloride was distilled off under reduced pressure.As a result, 3
-Methyl-4-chloroethoxyacetophenone is 40.
9 g (193 mmol) was obtained in a yield of 90%.

Then 6.60 g (95 mmol) of hydroxylamine hydrochloride and 4.96 g (47 mmol) of sodium carbonate.
Nonkongo ethanol water? Under water cooling to 150ml of liquid, 3-
Methyl-4-chloroethoxyacetophenone 15.3g
(72 mmol) was added and stirred at room temperature for 24 hours. 300 mj of reactants! of water and extracted with ethyl ether. After drying the extract over sodium sulfate, ethyl ether was distilled off under reduced pressure to obtain 14.0 g (62 mmol) of 3-methyl-4-chloroethoxyacetophenone oxime in a yield of 86%.

3-Methyl-4-chloroethoxyacetophenone oxime 14. Og (61 mmol) was dissolved in 100 ml of ethanol, 6 g of 5% palladium-attached activated carbon was added thereto, and the mixture was stirred at room temperature under a hydrogen atmosphere for 12 hours. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure and extracted with ethyl ether. After drying the extract over sodium sulfate, ethyl ether was distilled off under reduced pressure to obtain 3-methyl-4-chloroethoxy-α-methylhensylamine, which is a benzylamine 3M' compound represented by the following formula: 10.8 g (yield 82%) was obtained.

Formula Reference Example 3 (Synthesis of hensylamine derivative) 27.2 fK (200 mmol) of 2.6-cyphthylanisole and 18.8 g (240 mmol) of acetyl chloride were mixed with 250 mj of methylene chloride! 32.0 g (240 mmol) of aluminum chloride was gradually added while stirring under water cooling, and the mixture was stirred for 20 minutes under water cooling. after that,
The reaction mixture was added to 5% hydrochloric acid at 1200 mA and separated into an aqueous layer and an organic layer. The obtained organic layer was washed with 5% sodium carbonate (aqueous solution) overnight, dried over sodium sulfate, and methylene chloride was distilled off under reduced pressure. As a result, the product is 3
, 5-dimethyl-4-methoxyacetophenone is 33.
8 g (190 mmol) was obtained with a yield of 95%. This 3,5-dimethyl-4-meth)quinacetophenone 17
．． 8 g (100 mmol) and ammonium formate 25.2
g (400 mmol) and stirred at 180°C for 5 hours.

The reaction mixture was dissolved in 200 mff of benzene, washed with water, dried with sodium chloride sulfate, and then benzene was distilled off under reduced pressure. 5% sodium hydroxide in the product after benzene distillation?
Yo) 300mj at night! was added and stirred at 70°C for 26 hours. After cooling, ethyl ether 200m7! was added, and the organic layer was separated.

After drying this organic layer over sodium sulfate, ethyl ether was distilled off under reduced pressure.

The residue was distilled under reduced pressure (95-96°C/1.5mmHg) to obtain 3, which is a benzylamine derivative represented by the following formula.
11.0 g (yield 61%) of 5-dimethyl-4-methoxy-α-methylbenzylamine was obtained.

2 Production Examples 1 to 30 (Production of triazine derivatives) 2.6 Atsuguchi 4-amino-5-) riazine 16.4 g (0,
1 mole) to 55g of acetone? To this was added 0.1 mol of the benzylamine derivative shown in Table 1, followed by 8.4 mol of sodium bicarbonate dissolved in 60 g of water.
g (0.1 mol) was added with stirring at 0-5°C. After the addition, the mixture was gradually warmed to 50° C. over 1 hour.

After heating, the mixture is cooled and the product is separated and washed with water.

After drying, the desired triazine derivative was obtained. The yield, yield and analysis results of this product are shown in Table 1, and the structural formula is shown in Table 2.

Production Examples 31 to 35 (Production of triazine derivative) Using 10 mmol of the specified triazine derivative produced in the above production example as a raw material, after dissolving it in 201 Tll of methanol,
2.31 g (12 mmol) of 8% sodium methylate
was added and heated to reflux while stirring for 14 hours. After distilling off methanol under reduced pressure, it was dissolved in 50 ml of chloroform,
Washed with water.

After drying the chloroform layer over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was developed on silica gel column chromatography (developing solvent: toluene/ethyl acetate).
V 7 = 8/2) was purified and recrystallized from a mixture of ethanol and water to obtain triazine derivative 4 as white crystals.

The yield, yield, analysis results, etc. of this product are shown in Table 3, and the structural formula is shown in Table 4.

Production Example 36 (Production of triazine derivative) The same procedure as in Production Example 31 was carried out except that 0.68 g (12 mmol) of sodium ethylate was used instead of 28% sodium methylate. Ta. The results are shown in Tables 3 and 4.

Examples 1 to 36 (1) Preparation of herbicide 97 parts by weight of talc (trade name: Nidicrite) as a carrier, alkylaryl sulfonate (trade name: Neopelle 7X, Kao Atlas Gtl!!) as a surfactant. 1
．． 5 parts by weight and nonionic and anionic surfactants (trade name: Solpol 800A.

1.5 parts by weight of Toho Chemical Industries (porcelain) was uniformly ground and mixed to obtain a carrier for wettable powders.

90 parts by weight of this wettable powder carrier and 10 parts by weight of the triazine derivatives obtained in Production Examples 1 to 13 were uniformly ground and mixed to obtain a herbicide.

(2) Biological test (warm water soil treatment test) Fill paddy soil in a 1/1 S5O0R porcelain bot, and uniformly sow seeds of Japanese field grass, Japanese cypress, broad-leaved weeds (Kikashigusa, Konagi), and Hokurui on the surface layer. ,
In addition, I repaired the tubers of Mizugaya vine and Urikawa,
Two-leaf stage paddy rice was transplanted.

Thereafter, when the weeds germinated, a predetermined amount of the diluted herbicide obtained in (1) above was uniformly dropped onto the water surface to treat the weeds, and then the pots were left in a greenhouse and watered at appropriate times.

Table 5 shows the results of investigating the herbicidal effect and rice damage after 20 days of chemical treatment. The drug amount is expressed as the amount of active ingredient per 10 ares. In addition, paddy rice damage and herbicidal effects were measured using air-dried samples and expressed as follows.

Degree of phytotoxicity Paddy rice phytotoxicity (vs. non-treated area) 0
100% 1 95-99% 2 90-94% 3 80-89% 4 60-79% 5 50-69% Degree of herbicidal effect Weeding effect (vs. untreated area) 0
100% 1 61-99% 2 21-60% 3 11-20% 4 1-10% 5 0 White Comparative Example 1 In Example 1, Triazine X3 produced in Production Example 1
Example 1 except that 2-methylthio-4,6-bis(ethylamino)-s-triazine (-ship name: Simetrine), represented by 2 (A) below, was used instead of 3 bodies. A similar operation was performed.

The results are shown in Table 5.

Comparative Example 2 In Example 1, instead of the triazine derivative produced in Production Example 1, 2-methylthio4-methylamino-6-(α,α-dimethylbenzyl Amino)-3-triazine (Special Publication No. 49-8261
Mulberry cultivation was carried out in the same manner as in Example 1, except that the same method as in Example 1 was used. The results are shown in Table 5.

Comparative Example 3 In Example 1, triazine 3. produced in Production Example 1.
W Instead of the A body, 2- expressed by the following formula [C]
Chloro-4-isopropylamino-6-(α,α-dimethylhensylamino)-s-triazine (Japanese Patent Publication No. 1973-
The same operation as in Example 1 was carried out except that 8262 Publication) was used. The results are shown in Table 5.

Claims (4)

[Claims] (1) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, X^1, X^2, and X^3 are hydrogen atoms, respectively.
Halogen atom, nitro group, haloalkyl group having 1 to 4 carbon atoms, haloalkoxy group having 1 to 4 carbon atoms, alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 4 carbon atoms, or alkylthio having 1 to 4 carbon atoms represents a group, and R^1 has 1 to 1 carbon atoms.
4 represents an alkyl group, and Y represents a halogen atom or an alkoxy group having 1 to 4 carbon atoms. ] A triazine derivative represented by (2) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, X^1, X^2, and X^3 are hydrogen atoms,
Halogen atom, nitro group, haloalkyl group having 1 to 4 carbon atoms, haloalkoxy group having 1 to 4 carbon atoms, alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 4 carbon atoms, or alkylthio having 1 to 4 carbon atoms represents a group, and R^1 has 1 to 1 carbon atoms.
4 shows the alkyl group. [In the formula, Y^1 and Y^2 each represent a halogen atom. ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ which are characterized by reacting dihalogenated aminotriazine represented by
is the same as above. ] A method for producing a triazine derivative represented by: (3) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, X^1, X^2, and X^3 are hydrogen atoms, respectively.
Halogen atom, nitro group, haloalkyl group having 1 to 4 carbon atoms, haloalkoxy group having 1 to 4 carbon atoms, alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 4 carbon atoms, or alkylthio having 1 to 4 carbon atoms represents a group, and R^1 has 1 to 1 carbon atoms.
4 shows the alkyl group. [In the formula, Y^1 and Y^2 each represent a halogen atom. ] By reacting the dihalogenated aminotriazine represented by the general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, X^1, X^2, X^3, Y^1 and R^1
is the same as above. ] A triazine derivative represented by is produced, and then the derivative is given the general formula R^2OM_1_/_n [wherein R^2 represents an alkyl group having 1 to 4 carbon atoms, and M represents an alkali metal or an alkaline earth metal. show. Further, n indicates the valence of M. ] There are general formulas ▲ mathematical formulas, chemical formulas, tables, etc. that are characterized by reacting alcoholates represented by
is the same as above. ] A method for producing a triazine derivative represented by: (4) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, X^1, X^2, and X^3 are hydrogen atoms, respectively.
Halogen atom, nitro group, haloalkyl group having 1 to 4 carbon atoms, haloalkoxy group having 1 to 4 carbon atoms, alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 4 carbon atoms, or alkylthio having 1 to 4 carbon atoms represents a group, and R^1 has 1 to 1 carbon atoms.
4 represents an alkyl group, and Y represents a halogen atom or an alkoxy group having 1 to 4 carbon atoms. ] A herbicide containing a triazine derivative represented by the following as an active ingredient.