JPS6351379A - Triazine derivative, production thereof and herbicide containing said derivative as active ingredient - Google Patents

Abstract

NEW MATERIAL:A triazine shown by formula I [one of X<1>, X<2> and X<3> is H and the other two are 1-4C alkyl, 1-4C alkoxy, 1-4C alkylthio, etc.; R<1> is 1-4C alkyl; R<2> is halogen, 1-4C halogen-substituted alkyl, 1-4C alkoxy, etc.; R<3> is NH2, NHCOR<4> or N=CHR<5> (R<4> is H, 1-4C alkyl, etc.; R<5> is 1-4C alkyl, etc.) with the proviso that a case where X<1> and X<2> are 1-4C alkyl, 1-4C alkoxy, etc., X<3> is H, R<2> is 1-4C alkylthio and R<3> is NH2 at the same time is omitted]. EXAMPLE:2-Amino-4-( 3'-methyl-4'-methoxy-alpha-methylbenzylamino )-6-trifluorome thyl-S-triazine. USE:Is useful as a herbicide having no phytotoxicity to rice plant. PREPARATION:A compound shown by formula II is reacted with a compound shown by formula III to give a reaction product, which is reacted with a compound shown by formula IV to give a compound shown 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] Conventionally, various compounds have been known as triazine herbicides. -Methylthio=4,8-bis(alkylamino)-3-triazine derivatives have strong herbicidal activity and are known to be effective as herbicides.

However, for example 2-methylthio-4,6-bis(
The effectiveness of ethylamino)-s-triazine 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)-
A rice herbicide in which the alkylamino group of a 5-triazi/or 2-alkylthio-4,6-bis(alkylamino)-5-) liazine derivative is substituted with an α,α-dimethylbenzylamino group has been proposed ( Special Public Service 1978-828
1, Japanese Patent Publication No. 49-8282), these compounds have no phytotoxic effects on paddy rice and are effective against annual weeds, but are extremely effective against perennial weeds, which are currently a problem. Less effective.

In addition, 2-amino-4-benzylamino-6-(trifluoromethyl)-S-) riazine has also been developed as a herbicide (U.S. Pat. No. 3,816,419 and U.S. Pat. No. 3,932,187). It has the disadvantage that it does not have a sufficient herbicidal effect and is highly harmful to paddy rice.

[Problems to be Solved by the Invention] The present inventors have solved the above-mentioned problems with conventional herbicides, and have achieved almost the same effect under various soil and temperature conditions, while causing no chemical damage to paddy rice. We conducted intensive research to develop a completely new herbicide that can exhibit excellent herbicide effects against a variety of weeds ranging from annual to perennial weeds. In the course of this research, the present inventors have already developed triazine derivatives as shown in JP-A No. 81-140569, and are also conducting intensive research to develop herbicides with improved herbicidal activity or less phytotoxicity. layered. 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 has the following characteristics: General formula [where x+, X2. One of X3 represents a hydrogen atom, and the other two represent an alkyl group having 1 to 4 carbon atoms and an alkoxy group having 1 to 4 carbon atoms.

Represents an alkylthio group having 1 to 4 carbon atoms, a halogen atom, or a halogen-substituted alkoxy group having 1 to 4 carbon atoms, and R1
represents an alkyl group having 1 to 4 carbon atoms; R2 is a halogen atom, a halogen-substituted alkyl group having 1 to 4 carbon atoms, and 1 carbon number;
~4 alkoxy group or C1-4 furkylthio group L, R31tNH2, N=CHR5alyl lf
N=CHR5 (here R4 is a hydrogen atom, carbon number 1-4
R5 is an alkyl group having 1 to 4 carbon atoms, a substituted alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a fulkenyl group having 2 to 5 carbon atoms; R5 is an alkyl group having 1 to 4 carbon atoms; 4 alkoxy group or an alkylamino group having 1 to 4 carbon atoms. ), provided that XI and X2 are an alkyl group having 1 to 4 carbon atoms and an alkoxy group having 1 to 4 carbon atoms, respectively.

is an alkylthio group having 1 to 4 carbon atoms or a halogen atom, x3 is a hydrogen atom, and R2 is an alkylthio group having 1 to 4 carbon atoms, and at the same time R3 is NO3
and providing a triazine derivative represented by:

General formula [wherein, XI, x2. X3. R1 is the same as above, and X is a halogen atom. A salt of a benzylamine derivative represented by J is reacted with a cyanoguanidine represented by NH2R2N-C-NH-CM to form a compound of the general formula [wherein XI, X2. X3. Producing a salt of a benzyl big 7-nido conductor represented by R1, The general formula [wherein XI, x2. x3.117+, )72'
provides the same method as above for producing a triazine derivative represented by (hereinafter referred to as "Method-1").

Further, the present invention further advances the above method-1 to provide the general formula [1
The substituent R3 in the triazine derivative is NHCOR4
Also provided are methods for producing compounds that are N-C)IR5. That is, the general formula [I-A
A triazine derivative (amine group-containing triazine conductor) represented by 1 is added with a carboxylic acid halide represented by the general formula % formula % [[wherein R4 and X are the same as above], a carboxylic acid halide represented by the general formula % formula % [] [In the formula, R4 is the same as above, a carboxylic acid represented by the general formula % formula % [] [In the formula, R4 is the same as above,] a carboxylic acid anhydride represented by the general formula % formula % [] [In the formula, R4 is the same as above, and R7 has 1 to 4 carbon atoms.
represents an alkyl group. A general formula characterized by reacting a carboxylic acid ester represented by [Formula %] C in the formula XI, X2. X3. R1, R2', R4
Same as above] A method for producing a triazine derivative represented by (hereinafter referred to as "Method-2") and Akaharu 4-General formula C, where Xl, X2. X3. R1 is the same as above,
R2' hahalogen atom, alkoxy group having 1 to 4 carbon atoms.

The above general formula [VI] is added to the amino group-containing triazine derivative represented by the alkylthio group having 1 to 4 carbon atoms.
Carboxylic acid halide, - general formula [■ carboxylic acid, general formula [■ carboxylic acid anhydride or general formula]
General formula characterized by reacting a carboxylic acid ester of xJ...[I-8'] c In the formula, XI, X2. X3.1171.1172”
, R4 is the same as above, ] (hereinafter referred to as "Method-3") The group-containing triazine derivative is an aldehyde represented by the general formula % [] [where R5 is the same as above] or the general formula % [[] [where R5 and R7 are the same as above] . ] [wherein x1. x2. x3. R1, R2', R5
is the same as above, a method for producing a triazine derivative represented by 1 (hereinafter referred to as "method-4"), and ii. Formula [wherein XI, X2. X3. R1, R2", R5
C. Same as above, a method for producing a triazine derivative represented by 1 (hereinafter referred to as "Method-5") is provided.

[Includes all 1-C'l. ) A herbicide containing a triazine derivative represented by the following as an active ingredient is also provided.

The compound represented by the general formula [I] is triasif F
J, conductor Te J'l, where xl, x2. X3. R1,
R2o and R3 are as described above. That is, XI
.

x2. One of x3 represents a hydrogen atom, and each of the other two represents an alkyl group having 1 to 4 carbon atoms such as a methyl group, an ethyl group, an isopropyl group, a methoxy group, an ethoxy group, a normal propoxy group, an inpropoxy group, etc. an alkoxy group having 1 to 4 carbon atoms, a furkylthio group having 1 to 4 carbon atoms such as a methylthio group, an ethylthio group, a propylthio group, a halogen atom such as a chlorine atom, a bromine atom, a fluorine atom, an iodine atom, or a monochloromethoxy group, 1 to 4 carbon atoms such as difluoromethoxy group, monochloroethoxy group, monofluoromethoxy group, trifluoromethoxy group, etc.
1171 represents a halogen-substituted alkoxy group, and 1171 represents a methyl group, ethyl group, propyl group (n-, i-propino group), butyl group (n-9i-, sec-, tert-
R2 is a halogen atom such as a chlorine atom, a bromine atom, a fluorine atom, an iodine atom, a trifluoromethyl group, a trichloromethyl group, a trichloroethyl group, a dichloroethyl group, etc. Ethyl group.

Tetrafluoroethyl group, monochloromethyl group.

A halogen-substituted alkyl group having 1 to 4 carbon atoms such as a monobromomethyl group or a monofluoromethyl group, or a halogen-substituted alkyl group having 1 to 4 carbon atoms such as a methylthio group, an ethylthio group, or a propylthio group.
4 shows the alkylthio group.

Also, R3 is NO3, NHCOR' or N=C:
HR5, where R4 of NHCOR4 is a hydrogen atom,
Alkyl groups having 1 to 4 carbon atoms such as methyl group, ethyl group, propyl group, methoxymethyl group, methylthiomethyl group,
Various substituted alkyl groups having 1 to 4 carbon atoms such as chloromethyl group, ethoxymethyl group, ethylthio-methyl group, and bromomethyl group; cycloalkyl groups having 3 to 6 carbon atoms such as cyclopropyl group, cyclobutyl group, and cyclohexyl group; Further, R of N-CHR5 indicates a fulganyl group having 2 to 5 carbon atoms such as a vinyl group, propenyl group, or allyl group.
5 has 1 to 1 carbon atoms such as methyl group, ethyl group, propyl group, etc.
4 alkyl group, an alkoxy group having 1 to 4 carbon atoms such as a methoxy group, ethoxy group, and propoxy group, or an alkylamine group having 1 to 4 carbon atoms such as a monomethylamine group, dimethylamine group, monoethylamino group, and diethylamino group 7 Indicates the group.

There are various specific examples of the trichoton derivatives of the present invention, but in addition to the compounds obtained in the production examples described below, there are
-amino-4-(3',4'-dimethoxy-α-methylbenzylamino)-6-)lifluoromethyl-s-triazine, 2-amino-4-(3',5'-dimethyl-
α-methylbenzylamino)-6-trifluoromethyl-s-triazine, 2-amino-4-(3'-ethyl-
4'-Methoxy-α-methylbenzylamino)-6-trifluoromethyl-5-triazine, 2-amino-4-
(3'-methyl-4'-difluoromethoxy-α-methylbenzylamino)-61lifluoromethyl-5-triazine, 2-amino-4-(3'-methyl-4'-trifluoromethoxy-α-methyl benzylamino)-6-
Trifluoromethyl-5-)riazine, 2-amino-4
-(3'-Methyl-4'-ethoxy-α-methylbenzylamino)-6-trifluoromethyl-5-)riazine, 2-amino-4-(3'-methoxy-4'-methyl-
α-methylbenzylamino)-6-α, α, β, β-tetrafluoroethyl-3-triazine, 2-amino-4
-(3'-methoxy-4'-methyl-α-methylbenzylamino)-6-fluoromethyl-3-)riazine, 2
-7 minnow 4-(3'-methoxy-4'-methyl-α-
Methylbenzylaminochloromethyl-s-triazine, 2-amino-4- (
3'-Methyl-4'-methoxy-α-methylbenzylamine)-6-trichloromethyl-S-triazine, 2-
Amino-4-(3'-methyl-4'-methoxy-α-methylbenzylamino)-6-bromomethyl-S-)riazine, 2-amino-4-(3'-methyl-4'-bromo-α- methylbenzylamino)-6-trifluoromethyl-S-)riazine, 2-amino-4-(3'-methyl-4'-methoxy-α-ethylbenzylamino)-6-
α,α-dichloroethyl-S triazine, 2-amino-4-(3'-methoxy-4'-methyl-α-ethylbenzylamino)-6-α,α-dichloroethyl-S triazine, 2-amino-4- (3'-methoxy-4'-
Methyl-α-ethylbenzylamino)-6-α,α,β
, β-tetrafluoroethyl-s-triazine, 2-amino-4-(3'-methyl-4'-methoxy-α-ethylbenzylamino)-6-α, α, β, β-tetrafluoroethyl-S -triazine, 2-7 cetylamine 4-
(3'-methyl-4'-methoxy-α-methylbenzylamino)-6-trifluoromethyl-S-triazine,
2-acetylami-4-(3'-methyl-4'-methoxyα-methylbenzylamino)-6-α, α, β, β
-tetrafluoroethyl-S-) liazine, 2-7 cetylami-4-(3'-methyl-41-methoxy-α-methylbenzylamino)-6-α,α-dichloroethyl-S-triazine.

2-Propionylamino-4-(3'-methyl-4'-methoxyα-methylbenzylamino)-6-trifluoromethyl-S-) riazine, 2-methoxymethylcarbonylamino-4-(3'-methyl-4 '-Methoxy-
α-methylbenzylamino)-6-trifluoromethyl-S-triazine, 2-methoxymethylcarbonylamino-4-(3'-methyl-4'-methoxy-α-methylbenzylamino)-6-α,α- Dichloroethyl-triazine, 2-methoxymethylcarbonylamino-4
- (3'-Methyl-4'-methoxy-α-methylbenzylamino)-6-α,α,β,β,-tetrafluoroethyl-S-triazine, 2-acetylamino-4-(
3'-Methoxy-4'-methyl-α-methylbenzylamino)-6-)lifluoromethyl-S-triazine, 2
-acetylamino-4-(3'-methoxy-4'-methyl-α-methylbenzylamino)-6-a, ct, β,
β-tetra,), oroethyl-5-)riazine, 2-acetylamino-4-(3'-methoxy-41-methyl-
α-methylbenzylamino)-6-α, α-dichloroethyl-s-triazine, 2-propionylamino-4-
(3'-methoxy-47-methyl-α-methylbenzylamino)-6-trifluoromethyl-5-) riazine,
2-methoxycarbonylamino-4-(3'-methoxy-4'-methyl-α-methylbenzylamino)-6-trifluoromethyl-s-triazine, 2-inbutyleneimino-4-(3'-methoxy- 4'-Methyl-α-methylbenzylamino)-6-trifluoromethyl-5-
) riazine, 2-propyleneimino-4-(3'-methoxy-4'-methyl-α-methylbenzylamino)-6
-trifluoromethyl-s-triazine, 2-isobutyleneimino-4-(3'-methyl-4'-methoxy-α
-methylbenzylamino)-6-1lifluoromethyl-
S-triazine, 2-propyleneimino-47(3'-
Methyl-4'-methoxy-α-methylbenzylamino)
-6-Trifluoromethyl-s-triazine, 2-imptyleneimie/-4-(3'-methyl-4'-methoxy-α-methylbenzylamino)-6-α, α, β, β-
Tetrafluoroethyl-s-triazine, 2-isobutyleneimino-4-(3'-methyl-4'-methoxy-α
-methylbenzylamino)-6-α,α-dichloroethyl-5-)riazine, 2-methylthio-4-7cetylamino-6-(3'-methoxy-4'-methyl-α-methylbenzylamino)-s-triazine , 2-methylthio-4-propionylamino-6-(3'-methoxy-4
'-Methyl-α-methylbenzylamino>-s-triazine, 2-methylthio-4-methoxymethylcarbonylamino-6-(3'-methoxy-4'-methyl-α-methylbenzylamino)-S-)riazine , 2-methylthio-4-cyclopropylcarbonylamino-6-(3'
-methoxy-4'-methyl-α-methylbenzylamino)-s-1 riazine, 2-methylthio-4-7cetylamino-6-(3'-methyl-4'-nitoxy-α-methylbenzylamino)-5 -) riazine, 2-methylthio-4-acetylamino-6-(3'-ethyl-4'-methoxy-α-methylbenzylamino)-3-) riazine, 2-methylthio-4-acetylamino-6-( 3'-
Methyl-4'-methoxy-α-ethylbenzylamino)
-S-triazine, 2-ethylthio-4-7cetylamino-6-(3'-methyl-4'-methoxy-α-methylbenzylamino)-5-triazine, 2-ethoxy-4
-acetylamino-6-(3'-methyl-4'-methoxy-α-methylbenzylamino)-5-triazine, 2
-Methylthio-4-inbutyleneimino-6-(3'-
methoxy-4'-methyl-α-methylbenzylamino)
-s-triazine.

2-methylthio-4-propyleneimino-6-(3'-
methoxy-4'-methyl-α-methylbenzylamino)
-S-)Ryazine, 2-methylthio-4-propyleneimino-6-(3'-methyl-4'-methoxy-α-methylbenzylamino)-S-)Ryazine, 2-ethylthio-4-inbutyleneimino- 6-(3'-methyl-41
-methoxy-α-methylbenzylamino)-S-triazine, 2-methoxy-4-inbutyleneimino-6-(
3'-Methyl-4'-methoxy-α-methylbenzylamino)-s-) riazine, 2-chloro-4-inbutyleneimino-6, -(3'-methyl-4'-methoxy-α
-methylbenzylamino)-1-) riazine, and the like.

The triazine derivative of the present invention represented by the above general formula [I] can be produced by various methods. Among them, the above-mentioned methods 1 to 5 are cited as efficient manufacturing methods.

According to method-1, a salt of a benzylamine rust conductor represented by the general formula [11] is reacted with cyanoguanidine,
By obtaining a salt of a benzyl biguanide derivative represented by general formula [m] and reacting it with an alkyl ester represented by general formula [IV], the desired general formula [I
-A] A triazine derivative represented by (this corresponds to a part of the triazine derivative of general formula [I], i.e.,
A triazine derivative in which R2 in formula [I] is a halogen-substituted alkyl group having 1 to 4 carbon atoms, and R3 is N)12. ) is obtained.

There are various salts of the benzylamine derivative represented by the general formula [11]. XI in general formula [II], X2. X3 and R1 are as described above, specifically, a substituent (X.

X2. X3. A salt of a benzylamine derivative having R1) may be selected. Note that this benzylamine derivative may be a free amine or may be in the form of a hydrochloride or the like.

Although various methods can be considered for producing the benzylamino derivative represented by the above general formula [II], the following method is usually used.

That is, the general formula [where x+, ×2. x3 is the same as above, ] and a di-substituted benzene represented by the general formula RICOX C formula,
R1 and Formula [wherein, R1, Xl, X2. X3 is 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 R1, Xl, X2. x3 is the same as above, to obtain an N-formylbenzylamine derivative represented by . 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, and then treated with an acid such as concentrated hydrochloric acid, a salt of a benzylamine derivative represented by the general formula [11] can be obtained. can get.

Alternatively, oxime (phenone oxime derivative) is produced by reacting the phenone derivative represented by the above general formula [Xi] with hydroxylamine instead of ammonium formate, and this is reduced with an alkali metal such as sodium metal in alcohol. Alternatively, after catalytic reduction, treatment with an acid such as concentrated aX acid yields the desired salt of a benzylamine derivative represented by the general formula [11F].

Furthermore, the general formula [wherein, XI, X2. The cyanobenzene derivative represented by the formula RIMgX
A Grignard reagent represented by [R1 and The salt of the benzylamino derivative of general formula [11] can also be produced by reacting with ammonium formate, followed by hydrolysis and treatment with an acid such as 'a hydrochloric acid.

In method-1 of the present invention, the salt of the benzylamine derivative represented by the general formula [11] thus obtained is first reacted with cyanoguanidine. In this reaction, it is sufficient to use the recompounds in approximately equimolar ratios, and a solvent is not necessarily required, but alcohols such as methanol, ethanol, and impropatol, and cyclic cultures such as acetone, methylethyln, decalin, and alkylnaphthalenes can be used. Hydrogen, carbon tetrachloride, ethylene dichloride, chlorobenzene,
Chlorinated hydrocarbons such as dichlorobenzene, ethers such as tetrahydrofuran and dioxane, and even kerosene can also be used. Furthermore, it is also effective to add a deoxidizing agent (dehydrohalogenating agent) such as sodium hydrogen carbonate or triethylamine to this reaction system. Furthermore, the reaction temperature is not particularly limited, and ranges from low to high temperatures, specifically from 80 to 200
The process progresses satisfactorily in the ℃ range.

Through this reaction, a salt of the benzyl biguanide derivative represented by the general formula [I[I] is obtained, and the method of the present invention-1
Then, the alkyl ester R2°G of the general formula [171]
By reacting OOR6, the desired general formula [
A triazine derivative represented by I-Al is prepared. This reaction usually uses methanol.

Alcohols such as ethanol and impropatul, various ketones, aliphatic hydrocarbons, and various ethers.

The process proceeds efficiently at about 10 to 100°C in the presence of a catalyst such as a base in a solvent such as various cyclic hydrocarbons or chlorinated hydrocarbons.

Subsequently, in Method-2 and Method-3 of the present invention, the triazine derivative (amino group-containing triazine derivative) of the general formula [l-Al or general formula [1-A'l] obtained in the above-mentioned method-1, A carboxylic acid halide of general formula [VI].

A carboxylic acid of general formula [■], a carboxylic acid anhydride of general formula [VI] (7) or a carboxylic acid ester of general formula [IX] are reacted. This reaction depends on the type of compound used, but when a carboxylic acid halide is used, usually 1 mole of the triazine derivative containing amine 7 groups of the general formula [I-Al or [1-A'l], The above carboxylic acid halide is used in a ratio of 1 to 3 times the mole, and although a solvent is not necessarily required, aromatic compounds such as benzene, toluene, xylene, rtb hydrogen, chloroform,
It is preferable to use halogenated hydrocarbons such as methylene chloride, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane and heptane, ethers such as tetrahydrofuran and ethyl ether, or basic solvents such as pyridine. It is also effective to add a base such as triethylamine to the system. In addition, there is no particular restriction on the reaction temperature, but it ranges from low to high temperatures, specifically -
It progresses satisfactorily in the range of 20''O to 80'O.

In addition, when using a carboxylic acid ester of general formula [IX], it is sufficient to use at least an equimolar amount of the amino group-containing triazine derivative of general formula [1-AI or general formula [I-A'l], and a solvent is not necessarily required. However, water, aromatic hydrocarbons such as benzene, toluene, xylene, acetone,
It is preferable to use ketones such as methyl ethyl ketone, aliphatic hydrocarbons such as hexane and heptane, ethers such as tetrahydrofuran and ethyl ether, alcohols such as methanol and ethanol, and further dimethylformamide and dimethyl sulfoxide as solvents.

Furthermore, sodium methoxide is added to this reaction system.

It is also effective to add bases such as sodium ethoxide, n-butyllithium, sodium hydride, and the like. Further, the reaction temperature is not particularly limited, but the reaction progresses satisfactorily at a temperature ranging from low to high temperatures, specifically from 10 to 100°C.

In addition, when using the carboxylic acid of the general formula [■] or the carboxylic acid anhydride of the general formula [■], it may be carried out in accordance with the case of using the above-mentioned carboxylic acid ester.

According to Method-2 and Method-3 of the present invention, the desired triazine derivatives represented by the general formula [I-B] and the general formula [1-B'] can be obtained by the above reaction. .

Furthermore, in Method-4 and Method-5 of the present invention, the triazine derivative (amino group-containing triazine derivative) of the general formula [I-Al or the general formula [I-A'J] obtained in the above method-1, respectively, An aldehyde of general formula [X] or an acetal of general formula [X[] is reacted.

In this reaction, the general formula [l-Al or the general formula [1-
The aldehyde of the general formula [X] or the acetal of the general formula [Xr] may be used in approximately equal moles to the amino group-containing triazine derivative of A'l.Although a solvent is not necessarily required, benzene, toluene, xylene, etc. Aromatic hydrocarbons such as chloroform, halogenated hydrocarbons such as methylene chloride, etc. can be used as a suitable solvent. moreover,
It is preferable to use a dehydrating agent such as potassium hydroxide and a catalyst such as para-toluenesulfonic acid in this reaction system, and
The reaction temperature is not particularly limited, and can range from low to high temperatures,
The process progresses satisfactorily within the range of 'θ to 100°C.

According to Method-4 and Method-5 of the present invention, the desired triazine derivatives represented by the general formula [l-C5 and the general formula [1-C'l] are obtained by the above reaction.

In addition, in the above methods 2 to 5, general formula [I
-A'1. [I-13'1. [In I-C'l) R2z
> (In the case of an alkoxy group or an alkylthio group having 1 to 4 carbon atoms, a compound in which R2 is a halogen atom is reacted with an alcoholade, an alkylmercaptide, or an alkylmercaptan to convert the halogen atom into an alkoxy group or an alkylthio group. It can also be manufactured.

In the method-1 to method-5 of the present invention described above, anti-[l-C
A triazine derivative represented by 1 and [IC']) is obtained with high purity and high yield.

The triazine derivative of the present invention produced in this manner is a novel compound that suppresses the germination and growth of weeds and has high selectivity, so it is suitable as a herbicide. In particular, triazine derivatives represented by the general formula [l-Al2 are particularly preferred since they exhibit extremely high herbicidal activity.

In addition, the herbicide of the present invention has excellent weed control properties for weeds such as broad-leaved weeds such as Prunus japonicus, azalea, and cyperus, and grasses of the Cyperaceae family such as Cyperus japonica, and grasses such as No. Not only is it effective, but it also has an excellent weeding effect on perennial weeds such as firefly, cypress, and weed, which are currently difficult to control.

Next, the herbicide of the present invention contains the compound of the above-mentioned invention, that is, the triazine derivative represented by the general formula [I], as an active ingredient, and these compounds are mixed with a liquid carrier such as a solvent or a fine mineral powder. It can be used by mixing it with a solid carrier such as, etc., and formulating it in the form of a wettable powder, an emulsion, a single powder, etc. A surfactant may be added to impart emulsifying properties, bidispersity, spreading properties, etc. during formulation.

When the herbicide of the present invention is used in the form of a wettable powder, the above-mentioned triazine derivative of the present invention is usually used as an active ingredient.
~55% by weight, a solid carrier of 40-88% by weight, and a surfactant of 2-5% by weight to prepare a composition, and when used in the form of an emulsion,
The triazine derivatives of the present invention are usually used as active ingredients.
50% by weight, solvent 35-75% by weight and surfactant 5
It may be prepared by blending at a ratio of ~15% by weight, on the other hand,
When used in the form of a powder, it usually contains 1 to 15% by weight of the triazine conductor of the present invention as an active ingredient and 80 to 80% by weight as a solid carrier.
It may be prepared by blending 97% by weight of surfactant and 2 to 5% by weight of surfactant. Furthermore, when used in the form of a single granule, 0.2 to 0.2 to 5% of the triazine derivative of the present invention is used as an active ingredient.
It may be prepared by blending 15% by weight of solid carrier, 8% to 97.8% by weight of solid carrier, and 2% to 5% by weight of surfactant.
Here, a fine mineral powder is used as the solid carrier, and examples of the fine mineral powder include oxides such as diatom, slaked lime, phosphates such as apatite, sulfates such as ceracola, talc, and pyroferrite. Examples include silicates such as clay, 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, and benzene, O-
Chlorinated hydrocarbons such as chlorotoluene, trichloromethane, trichlorethylene, alcohols such as cyclohexanol, amyl alcohol, ethylene glycol, ketones such as isophorone, cyclohexanone, cyclohexenyl-cyclohexanone, butyl cellosolve, dimethyl ethyl, methyl ethyl ether, etc. Examples include ethers, esters such as inpropyl acid, benzyl acetate, and methyl phthalate, amides such as dimethylformamide, and mixtures thereof.

Further, as the surfactant, any of anionic type, nonionic type, cationic type, and amphoteric ff1 (amino acid, betaine, etc.) can be used.

[Effects of the Invention] The triazine derivative of the novel compound represented by the general formula [1] of the present invention has a high herbicidal effect not only on annual weeds but also on perennial weeds, and has no chemical damage to paddy rice. It is extremely useful as a highly selective herbicide.

The herbicide of the present invention has general formula [I] 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, pyrazole herbicides, phosphate herbicides, and oxacyacin.

Furthermore, the herbicide of the present invention can be used in combination with insecticides, fungicides, plant growth regulators, fertilizers, etc., if necessary.

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, firefly, and cypress.

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

Reference Example 1 10.1 g (50 mmol) of 3-methyl-4-methoxy-α-methylbenzylamine hydrochloride, 4.2 g (50 mmol) of cyanoguanidine, and 35 layer 2 of 0-dichlorohensen were mixed, and 140 The mixture was heated and stirred at -150°C for 10 hours. Thereafter, the reaction mixture was cooled, and the precipitate deposited was collected in a furnace and 5mf! Then, the toluene was distilled off under reduced pressure to obtain 14.0 g of solid 3-methyl-4-methoxy-α-methylbenzylbiguanide hydrochloride (yield: 98%). The structural formula, yield, and yield of this product are shown in Table 1.

Reference Examples 2 to 12 In Reference Example 1, the raw material compound shown in Table 1 (di-substituted-α-alkylbenzylamine hydrochloride) was used instead of 3-methyl-4-methoxy-α-methylbenzylamine hydrochloride.
The same operation as in Reference Example 1 was performed except that 50 mmol was used. Table 1 shows the structural formula, charge collection, and yield of the obtained di-substituted -α-furkylbenzyl biguanide hydrochloride.

58! Example 1 0.23g of sodium in 10ml of dry methanol
(10 mmol) was gradually added to form sodium methoxide, and 3-methyl-4 obtained in Reference Example 1
-Methoxy-α-methylbenzylbiguanide hydrochloride 1.
3 g (5 mmol) was added and pressed for 30 minutes at room temperature, followed by 1.19 m of trifluoroacetic acid ethyl ester.
After the completion of the reaction, the contents were poured into 50 μP of water and extracted three times with 25+f of ethyl acetate. After drying this ethyl acetate layer over sodium sulfate, ethyl acetate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate = 4/1) and then recrystallized from hexane-ethyl ether to give white 2-amino-4-(3'-methyl-4 0.58 g (yield 34%) of '-methoxy[alpha]-methylbenzylamino)-6-trifluoromethyl-9-triazine (compound 1) was obtained. The yield, yield and analysis results of this product are shown in Table 2, and the structural formula is shown in Table 3.

Production Examples 2 to 5 Compounds 2 to 5 were obtained in the same manner as in Production Example 1, except that 10 mmol of the ester shown in Table 2 was used in place of trifluoroacetic acid ethyl ester. The yields, yields, and analysis results of these compounds are shown in Table 2, and the structural formulas are shown in Table 3.

Production Examples 6 to 12 Production Example 1 except that 5 mmol of G-substituted-α-alkylbenzylbiguanide hydrochloride shown in Table 2 was used in place of 3-methyl-4-methoxy-α-methylbenzylbiguanide hydrochloride. Compounds 6 to 12 were obtained by performing the same operation as above. The yields, yields, and analysis results of these compounds are shown in Table 2, and the structural formulas are shown in Table 3.

Production Examples 13 to 21 5 mmol of di-substituted-α-alkylbenzylbiguanide hydrochloride shown in Table 2 was used instead of 3-methyl-4-methoxy-α-methylbenzylbiguanide hydrochloride, and trifluoroacetic acid ethyl ester α, α− instead of
Except for using dichloropropion ugly methyl ester.
Compounds 13 to 21 were obtained by performing the same operation as in Production Example 1. The yields, yields, and analysis results of these compounds are shown in Table 2, and the structural formulas are shown in Table 3.

Production Example 22 3.05 g (IO mil) of 2-methylthio-4-amino-6-(3'-methyl-4'-methoxy-α-methylbenzylamino)-s-triazine shown as raw materials in Table 4 %le) to benzene2oW+I! 1.57 g (20 mmol) of triethylamine were added. While stirring under water cooling, add raw material II to Table 4.
After dropping 2.02 g (20 mmol) of acetyl chloride shown as , the mixture was stirred at room temperature for 3 hours, and then heated under reflux for 1 hour. After cooling, the benzene layer was washed with water, dried over sodium sulfate, and then benzene was distilled off under reduced pressure.

The residue was purified by silica gel column chromatography (developing solvent: toluene/ethyl acetate = 872), recrystallized from acetone-water, and white crystals of 2-methylthio-4-acetylamide/-6-(3'-methyl-4'-
1.74 g (yield: 50%) of methoxy-〇-methylbenzylamino)-5-) riazine (compound 22) was obtained.

The yield, yield and analysis results of this product are shown in Table 4, and the structural formula is shown in Table 5.

Production Examples 23 to 28 Raw material 1 (IO mmol) and raw material ■ (2
Compound 2 was prepared in the same manner as in Production Example 22 using 0 mmol).
3 to 29 were obtained. The yields, yields, and analysis results are shown in Table 4, and the structural formulas are shown in Table 5.

Production Example 30 3.30 g (10 mmol) of 2-methylthio-4-amino-6-(3',4'-dichloro-α-methylbenzylamino)-5-)riazine shown as raw material I in Table 4
28% sodium methoxide in methanol solution 1.93
g (10 mmol) and 10+aJ of methanol were added, and after heating to 50°C, methanol was distilled off under reduced pressure. To the residue was added 20 m2 of methyl acetate shown as raw material (2) in Table 4, and after heating to 5Q''C, 20 rR of water was added.

After washing the ethyl acetate layer with water, ethyl acetate was distilled off under reduced pressure.
The obtained solid was recrystallized from 7cetone-water to give white crystals of 2-methylthio-4-7cetylamino-6-(3
',4'-dichloro-α-methylbenzylamine)-
5-) 2.31g of riazine (compound 30) (yield: 6
2%). The yield, yield and analysis results of this product are shown in Table 4, and the structural formula is shown in Table 5.

Production Examples 31 to 36 Raw material I (1059 mol) and raw material II shown in Table 4
(Compounds 31 to 36 were obtained in the same manner as in Production Example 30 using 20tj. The yields, yields, and analysis results are shown in Table 4, and the structural formulas are shown in Table 5.

Production Example 37 3.05 g (10 mmol) of 2-methylthio-4-amino-6-(3'-methyl-4'-methoxy-α-methylbenzylamino)-3-triazine shown as the raw material in Table 4 was added. Dissolved in benzene 201.

Isobutyraldehyde 2.1 shown as raw material ■ in Table 4
8 g (30 mmol), para-toluenesulfonic acid 0.
05 g was added thereto, and the mixture was heated under reflux for 4 hours. After cooling, the benzene layer was washed with water, dried over sodium sulfate, and then distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (developing solvent ditoluene/ethyl acetate = 98/
2) and recrystallized from ethanol-water to give white crystals of 2-methylthio-4-inbutyleneimino-6-(3'-methyl-4'-methoxy-α-methylbenzylamino)- 5-) riazine (compound 37) with 2
．． 37 g (yield B: 6%) was obtained. The yield, yield and analysis results of this product are shown in Table 4, and the structural formula is shown in Table 5.

Production Examples 38-38 Raw material I (1059 mol) and raw material II shown in Table 4
Compounds 38 to 39 were obtained in the same manner as in Production Example 37 using (30 mmol). The yields, yields, and analysis results are shown in Table 4, and the structural formulas are shown in Table 5.

Production example 40 2-methylthio-4-amino-6-(3'-methyl-4
3.05 g (10 mmol) of phenyl formate
．． 47 g (12 mmol) and 1.46 g of phenol
The mixture was added and gradually heated to 70°C, and scuttling was confirmed. After the temperature reached 70°C, the mixture was heated and stirred for an additional 3 hours, and then allowed to cool. The resulting precipitate was filtered, washed with a small amount of ethyl acetate, and dried to obtain a white solid, 2-methylthio-4-formylamino-6-(3'-methyl-4'-methoxy-α-methylbenzylamino)-. , 1.87 g (yield 50%) of s-triazine (compound 40) was obtained. The yield, yield and analysis results of this product are shown in Table 4, and the structural formula is shown in Table 5.

Production example 41 2-methylthio-4-amino-6-(3'-methyl-4
3.05 g (10 mmol) of '-methoxy-α-methylbenzylamino)-5-triazine was dried, dissolved in 10 mj of benzene, and heated under reflux. N, N- to this
Dimethylformamide dimethyl acetal 3.57g
(30 mmol) and para-toluenesulfonic acid 0.0
4 g was added and heated under reflux for 1 hour. After cooling, the reaction solution was poured into water and extracted with benzene. The benzene layer was dried over sodium sulfate, and the benzene was distilled off under reduced pressure. The residue was recrystallized from ethanol-wood to give a white 2-methylthio-4
-ethoxymethyleneimino-6-(3'-methyl-4'
-methoxy-α-methylbenzylamino)-S-triazine (compound 41) in 1. asg (yield 55%) was obtained. The yield, yield and analysis results of this product are shown in Table 4, and the structural formula is shown in Table 5.

Examples 1 to 41 (1) Preparation of herbicide 97 parts of talc (trade name: Nidicrite) as a carrier, alkylaryl sulfonate (trade name: Neoperex, manufactured by Kao Atlas Co., Ltd.) as a surfactant.1. 5
Part II and nonionic and anionic surfactants (trade name: Nluball 800A).

A carrier for wettable powders was obtained by uniformly pulverizing and mixing 1.5 parts by weight (manufactured by Toho Kagaku Chogyo ■).

90 parts by weight of this wettable powder carrier and 10 parts by weight of the triazine derivatives obtained in Production Examples 1 to 41 were uniformly ground and mixed to obtain a herbicide.

(2) Biological test (flood soil treatment test) Fill a 1/15,500 are porcelain pot with paddy soil.
On the surface layer, weeds, cypress, and broad-leaved weeds (kikashigusa,
Seeds of Japanese cypress (Konagi) and Japanese firefly were sown uniformly, and tubers of Japanese cypress and Japanese cypress were also transplanted, and paddy rice at the two-leaf stage 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 6 shows the results of investigating the herbicidal effect and rice damage 20 days after the chemical solution treatment, and the amount of the drug is expressed as the amount of active ingredient per 10 ares. Also, paddy rice chemical damage.

The herbicidal effect was measured for each air-dried product and expressed as follows.

Degree of phytotoxicity Paddy rice phytotoxicity (vs. untreated plot) 0100% 1 95-99% 2 90-94% 3 80-88% 4 60-79% 5 50-69% Degree of herbicidal effect Weeding effect (vs. untreated plot) ratio) 0100
% 1 61-89% 2 21-60% 3 11-20% 4 1-10% 5 0% Comparative Production Example 1 In Example 1, the following formula [A ] Example 1 except that 2-methylthio-4,6-bis(ethylamine)-s-triazine (generic name: simetrine) was used.
The same operation was performed. The results are shown in Table 6.

Comparative Production Example 2 In Example 1, 2-methylthio-4-methylamino-6-(α,α-dimethylbenzylamino) represented by the following formula [B] was used instead of the triazine derivative produced in Production Example 1. -5-) Reazine (Special Publication No. 49-8281
The same operation as in Example 1 was carried out except that the same procedure as in Example 1 was used. The results are shown in Table 6.

Comparative Production Example 3 In Example 1, 2-chloro-4-isopropylamino-6-(α,α-dimethylbenzylamino) represented by the following formula [C] was used instead of the triazine derivative produced in Production Example 1. -S-triazine (Special Publication No. 49-826
The same operation as in Example 1 was carried out except that the same procedure as in Example 1 was used. The results are shown in Table 6.

Comparative Production Example 4 In Example 1, 2-amino-4-(α-methylbenzylamino)-6-1-lifluoromethyl represented by the following formula [D] was used instead of the triazine derivative produced in Production Example 1. -s-triazine (U.S. Pat. No. 3,816,419)
The same operation as in Example 1 was carried out except that the same procedure as in Example 1 was used. The results are shown in Table 6.

Claims (7)

[Claims] (1) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, one of X^1, X^2, and X^3 represents a hydrogen atom, and the other two each have 1 to 1 carbon atoms. 4 alkyl group, alkoxy group having 1 to 4 carbon atoms, 1 to 4 carbon atoms
alkylthio group, halogen atom or carbon number 1-4
represents a halogen-substituted alkoxy group, R^1 has 1 carbon number
~4 alkyl group, R^2 represents a halogen atom, a halogen-substituted 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, and R^3 represents NH_2, NHCOR^4 or N=C
HR^5 (where R^4 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a substituted alkyl group having 1 to 4 carbon atoms, or a hydrogen atom having 3 to 4 carbon atoms.
6 is a cycloalkyl group or an alkenyl group having 2 to 5 carbon atoms, and R^5 is an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkylamino group having 1 to 4 carbon atoms. . ) is shown. However, X^1 and X^2 are each an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, or a halogen atom, and X^3 is a hydrogen atom. Excludes the case where R^2 is an alkylthio group having 1 to 4 carbon atoms and R^3 is NH_2. ] A triazine derivative represented by. (2) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, one of X^1, X^2, and X^3 represents a hydrogen atom, and the other two each have a carbon number of 1 to 4 alkyl group, alkoxy group having 1 to 4 carbon atoms, 1 to 4 carbon atoms
alkylthio group, halogen atom or carbon number 1-4
represents a halogen-substituted alkoxy group, R^1 has 1 carbon number
~4 alkyl group, and X represents a halogen atom. ] A salt of a benzylamine derivative represented by the formula ▲mathematical formula,
There are chemical formulas, tables, etc. By reacting cyanoguanidine represented by ▼, a general formula ▲ Numerical formulas, chemical formulas, tables, etc. are available. Same as above. ] A salt of a benzyl biguanide derivative represented by
^6 [In the formula, R^2' represents a halogen-substituted alkyl group having 1 to 4 carbon atoms, and R^6 represents an alkyl group having 1 to 4 carbon atoms. ] There are general formulas ▲ mathematical formulas, chemical formulas, tables, etc. that are characterized by reacting alkyl esters represented by ▼ [In the formula, X^1, X^2, X^3, R^1, R^2' 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, one of X^1, X^2, and X^3 represents a hydrogen atom, and the other two each have a carbon number of 1 to 4 alkyl group, alkoxy group having 1 to 4 carbon atoms, 1 to 4 carbon atoms
alkylthio group, halogen atom or carbon number 1-4
represents a halogen-substituted alkoxy group, R^1 has 1 carbon number
~4 alkyl group, and X represents a halogen atom. ] A salt of a benzylamine derivative represented by the formula ▲mathematical formula,
There are chemical formulas, tables, etc. By reacting cyanoguanidine represented by ▼, a general formula ▲ Numerical formulas, chemical formulas, tables, etc. are available. Same as above. ] A salt of a benzyl biguanide derivative represented by
^6 [In the formula, R^2' represents a halogen-substituted alkyl group having 1 to 4 carbon atoms, and R^6 represents an alkyl group having 1 to 4 carbon atoms. ] By reacting an alkyl ester represented by the general formula ▲ mathematical formula, chemical formula, table, etc. ▼ [wherein, X^1, X^2, same. ], and then the amino group-containing triazine derivative has the general formula R^4COX [where R^4 is a hydrogen atom,
It represents an alkyl group having 1 to 4 carbon atoms, a substituted alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms, and X is the same as above. ] Carboxylic acid halide, general formula R^4
COOH [wherein R^4 is the same as above. ] Carboxylic acid represented by the general formula (R^4CO)_2O [where R^
4 is the same as above. ] or the general formula R^4COOR^7 [wherein R^4 is the same as above, and R^7 represents an alkyl group having 1 to 4 carbon atoms. ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, X^1, X^2, X^3, R^1, R^2] ′,
R^4 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, one of X^1, X^2, and X^3 represents a hydrogen atom, and the other two each have 1 to 1 carbon atoms. 4 alkyl group, alkoxy group having 1 to 4 carbon atoms, 1 to 4 carbon atoms
alkylthio group, halogen atom or carbon number 1-4
represents a halogen-substituted alkoxy group, R^1 has 1 carbon number
~4 alkyl group, and R^2'' represents a halogen atom, an alkylthio group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms.] The amino group-containing triazine derivative represented by the general formula R
^4COX [wherein R^4 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a substituted alkyl group having 1 to 4 carbon atoms, a 3 carbon number
-6 cycloalkyl group or C2-5 alkenyl group, and X represents a halogen atom. ] A carboxylic acid halide represented by the general formula R^4COOH [wherein R^4 is the same as above. ] Carboxylic acid represented by
General formula (R^4CO)_2O [wherein R^4 is the same as above. ] or the general formula R
^4COOR^7 [In the formula, R^4 is the same as above,
R^7 represents an alkyl group having 1 to 4 carbon atoms. ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, X^1, X^2, X^3, R^1, R^2] ″,
R^4 is the same as above. ] A method for producing a triazine derivative represented by: (5) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, one of X^1, X^2, and X^3 represents a hydrogen atom, and the other two each have a carbon number of 1 to 4 alkyl group, alkoxy group having 1 to 4 carbon atoms, 1 to 4 carbon atoms
alkylthio group, halogen atom or carbon number 1-4
represents a halogen-substituted alkoxy group, R^1 has 1 carbon number
~4 alkyl group, and X represents a halogen atom. ] A salt of a benzylamine derivative represented by the formula ▲mathematical formula,
There are chemical formulas, tables, etc. By reacting cyanoguanidine represented by ▼, a general formula ▲ Numerical formulas, chemical formulas, tables, etc. are available. Same as above. ] A salt of a benzyl biguanide derivative represented by
^6 [In the formula, R^2' represents a halogen-substituted alkyl group having 1 to 4 carbon atoms, and R^6 represents an alkyl group having 1 to 4 carbon atoms. ] By reacting an alkyl ester represented by the general formula ▲ mathematical formula, chemical formula, table, etc. ▼ [wherein, X^1, X^2, same. ] is produced, and then the amino group-containing triazine derivative is given the general formula R^5CHO [wherein R^5 is a carbon number of 1 to 1].
4 alkyl group, an alkoxy group having 1 to 4 carbon atoms, or an alkylamino group having 1 to 4 carbon atoms. ] or the general formula R^5CH(OR^7)_
2 [In the formula, R^5 is the same as above, and R^7 represents an alkyl group having 1 to 4 carbon atoms. ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, X^1, X^2, X^3, R^1, R^2',
R^5 is the same as above. ] A method for producing a triazine derivative represented by: (6) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, one of X^1, X^2, and X^3 represents a hydrogen atom, and the other two each have a carbon number of 1 to 4 alkyl group, alkoxy group having 1 to 4 carbon atoms, 1 to 4 carbon atoms
alkylthio group, halogen atom or carbon number 1-4
represents a halogen-substituted alkoxy group, R^1 has 1 carbon number
~4 alkyl group, and R^2'' represents a halogen atom, an alkylthio group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms.] The amino group-containing triazine derivative represented by the general formula R
^5CHO [wherein R^5 represents an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkylamino group having 1 to 4 carbon atoms. ] or the general formula R^5CH(OR^7)_2 [wherein R^
5 is the same as above, and R^7 represents an alkyl group having 1 to 4 carbon atoms. ] ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, X^1, X^2, X^3, R^1, R^2'',
R^5 is the same as above. ] A method for producing a triazine derivative represented by: (7) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, one of X^1, X^2, and X^3 represents a hydrogen atom, and the other two each have 1 to 1 carbon atoms. 4 alkyl group, alkoxy group having 1 to 4 carbon atoms, 1 to 4 carbon atoms
alkylthio group, halogen atom or carbon number 1-4
represents a halogen-substituted alkoxy group, R^1 has 1 carbon number
~4 alkyl group, R^2 represents a halogen atom, a halogen-substituted 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, and R^3 represents HH_2, HHCOR^4 or N=C
HR^5 (where R^4 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a substituted alkyl group having 1 to 4 carbon atoms, or a hydrogen atom having 3 to 4 carbon atoms.
6 is a cycloalkyl group or an alkenyl group having 2 to 5 carbon atoms, and R^5 is an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkylamino group having 1 to 4 carbon atoms. . ) is shown. However, X1 and X2 are each an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, or a halogen atom, and X3 is a hydrogen atom, and R^
2 is an alkylthio group having 1 to 4 carbon atoms, and at the same time R
Except when ^3 is NH_2. ] A herbicide containing a triazine derivative represented by the following as an active ingredient.