JPS61145166A - Novel 2,4-diaminopyridines - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to new 2,4-diaminopyrimidines, a process for their preparation and their use as plant protection agents, especially herbicides.

2,4-diaminopyrimidine of the species, e.g. 2.4
It is known that -bicyclopropylamino-5,6-cyclobiliminone can be used as a herbicide (DE-
O8 (German patent publication details) No. 2゜006.145
However, when used in small amounts, the action against various harmful plants is not satisfactory.

General formula (1) In the formula, R1 represents hydrogen or halogen, R2 represents furkyl which may optionally be substituted with halogen, or represents halogen or flukoxy, R represents furkyl, and Y represents oxygen or sulfur. Novel 2,4-noaminopyrimidines of the formula (A>general formula (II)), and Z represents branched or unbranched fullkylene, wherein R1 and (/R' have the meanings given above) , and X represents a halogen (preferably fluorine or salt J), initially a halodenopyrimidine of the formula (I[[) in which R', R4, Y and Z have the meanings given above, In the presence of a binder and, if appropriate, a diluent, the general formulas (]Va) and <IVb) (IVa) (It/b) in which R', R', R' , R', X, Y and Z have the above-mentioned meanings (first step), and then the two isomers are separated to form a pyrimidine of formula (Wa) The derivative is converted into ammonia (v) in a further reaction step.
and NH, (V) in the presence of an acid binder, if appropriate in the presence of a diluent, to give the py17S dine derivatives of formula (1) (
12 steps), or (B) general formula (Vl) in which Rl, R2 and X have the above-mentioned meanings 4-7
minopyrimicin with an amine of formula <1) - again by method (A
) to give a pyrimidine derivative of the formula (N R4 where R', R2, R', R', Y and Z have the meanings given above) It was discovered that it can be obtained by

If R2 represents halogen, this reaction can be carried out using the general formula (1
) and (1a) (1) (+,) in which R1, R2, R', R', X, Y and VZ have the meanings given above, giving a pyrimidine derivative isomer mixture of The piI7 micin derivative of (1) is isolated.

Furthermore, it has been discovered that new pyrimidine derivatives of the general formula (H) exhibit strong herbicidal properties.

The novel BiIJ sewing derivative of the general formula (1) of the present invention has a structure in which the 2-amino group has a straight or branched alkyl chain in which an oxygen or sulfur atom is inserted, and 4 It is distinguished from conventionally known pyrimidines by the presence of an unsubstituted amide 7 group at the position.

Surprisingly, the active compounds of formula (1) according to the invention are pyrimidine derivatives, which are traditionally known to be tolerated by crop plants;
For example, it is comparable to 2,4-biscyclopropylamine/-5,6-cyclobiliminone (known from DE-O8 (German Patent Publication No. 2,630,140)), but more clearly. It is highly active.

Among the pyrimidine derivatives of formula (1) according to the invention, preferred are those in which R' represents hydrogen, chlorine or fluorine, and R2 is chlorine, fluorine, alkoxy having 1 to 6 carbon atoms, or optionally chlorine and / or represents an alkyl having 1 to 6 carbon atoms optionally substituted by fluorine, R3 represents an alkyl having 1 to 6 carbon atoms, and R4 is hydrogen or having 1 to 6 carbon atoms Compounds which represent alkyl and Z represents a branched or unbranched alkylene group having 2 to 10 carbon atoms.

Among this group of compounds, particular preference is given to those in which R' represents hydrogen, chlorine or a radical, and R2 represents chlorine, fluorine, alkoxy having 1 to 3 carbon atoms, or optionally chlorine and / or represents an alkyl having 1 or 2 carbon atoms which may be substituted by fluorine, R3 represents an alkyl having 1 to 4 carbon atoms, and R4 represents hydrogen or an alkyl having 1 to 4 carbon atoms; is a compound of formula (1) in which Y represents oxygen or sulfur and Z represents a branched or unbranched alkylene group having 2 to 7 carbon atoms; .

For example, in method (A), 2,4,6-)rifmiropyrimicin and 3-medixypropylamine are used as starting materials and the 4,6-cyclotll-2-(
When 3-methodoxypropylamine)-pyrimidine is further reacted with ammonia, the reaction process can be roughly represented by the following formula: C1 or method (B) with 4-7 minnow 2.5.6 -) If lichlorobilimicin is used as a starting material and reacted with 3-methoxypropylamine, the reaction process can be roughly represented by the following formula.

Isolation by isomer separation (crystallization) Formula (U) gives a general definition of the halodefpyrimidine used as starting material. In this formula, R1 and V
R2 is preferably, or particularly preferably, when describing the compounds of the general formula according to the invention, 2'.

X represents the groups already mentioned as preferred or particularly preferred substituents, and X represents chlorine or fluorine. Halodenopyrimicins of formula (II) are known or can be prepared by known methods (see Examples).

The formula ([[[) gives a general definition of the amines further used as starting materials. In this formula, R.

R', Y and Z preferably or particularly preferably represent groups listed as preferred or particularly preferred substituents when describing the compound of formula (1) of the present invention. . Amines of formula (n[) are known or, like known compounds, can be prepared by known methods (e.g. Houben-Weyl, M.
etl+o'dcnder OrI? anisch
en CI+e-mie (organic chemistry method), X1
/ Volume 1, pages 548, 561 onwards, 4th edition 1! 357
(see U.S. Pat. No. 2,764,615).

Formula (IV) provides a general definition of the 4-7 virimicin used as a starting material. In this formula, R' and R2 preferably or particularly preferably represent the groups already mentioned as preferred or particularly preferred when describing the compounds of formula (I) according to the invention, and X is chlorine or fluorine. The 4-aminopyrimidine derivatives of formula 6 (l) are known or can be prepared by known methods (see Examples).

Diluents that can be used in process (A) and process (B) of the invention are organic solvents and water. Preferred organic solvents are hydrocarbons such as toluene, aliphatic ketones such as acetone, methyl ethyl ketone and diethyl ketone, and cycloaliphatic ethers such as tetrahydrofuran or dioxane. Mixtures of different organic solvents, mixtures of water-miscible organic solvents and water are also suitable for use as diluents.

Methods (A) and (B) of the invention can be carried out using acid acceptors. Particularly suitable are, for example, alkaline earth metal hydroxides and hydroxides of the alkali group, such as calcium hydroxide, sodium hydroxide or potassium hydroxide, as well as ammonia and tertiary aliphatic amines, such as triethylamine. However, the ami of formula (1),
It is also possible to use excess starting material.

In the process of the invention, the reaction temperature can be varied within a considerable range. The tIS1 step of method (A) is generally 130~
It is carried out at +150°C, preferably -20 to +50°C. The second stage is generally 80-150°C, preferably 90-150°C.
Carry out at 130°C. Method (B) is generally 80-150
It is carried out at a temperature of preferably 90 to 130°C.

The reaction is carried out in a pressure range of 1 to 10 bar.

When carrying out the method (A>) of the present invention, in the first step the formula (
Generally 1 to 1 mole of harodenopyrimidine in ■)
1.1 mol of amine of formula (I[[) and 1-1.2 mol of acid acceptor are used. It is possible to use amines of formula (I[[) as acid acceptors.

Preferably, the method is carried out using stoichiometric molar ratios. The same applies to the second stage as well as method (B).

The isomer mixtures obtained by these two methods can be separated in a simple manner using known methods, in particular by recrystallization, chromatography or steam distillation! (For example, DE-O
3 (German patent publication specification) 112.006,145
DE-O3 No. 2,630°140 and European Patent PAO, 114,575), whereby the desired specific isomer is obtained in sufficient purity.

The active compounds of the invention can be used as defoliants, desiccants, means of destruction of broad-leaved plants.
d-leaved plant! I) and can be used in particular as a weed killer. The term weed is to be understood as referring most broadly to all plants that grow in undesirable locations. Whether the compounds of the invention act as systemic herbicides or selective herbicides
It essentially depends on the amount used.

The active compounds according to the invention can be used, for example, against the following plants:

〉Progeny: Mustard genus (S 1napis),
L. eipiclius+,
Yaemugura JK (Galius), Chickweed (S Le
llaria), Matricaria
, Anthemis, G al insoga, Chenopodium I & (Che
nopodiu+w), Urtica
, Senecio, Amaran
thus), Suberihyu JX (Portulaca)
, X anthiuw, X anthiuw, X anthiuw
Convolvulus), Ipomoea (I pon
+oea), Polygonus, Sesbania, Ambro
sia), Cirsium, Carduus, 7deciml (Sonchus),
Solanum, Rori
ppa), Rotala
L 1ndernia), Lamium 14 (Lamium 14)
), V eronica , Abutil.

n), Emex genus (Eshoex), Datura 1
4 (Datura), Viola (V 1oln), Galeopsis (Galeopsis), Papaver (P a
paver) and Centaurea spp.
).

Cultivation of ゛: Gossypi
um), Glycine, B eta, Daucus, P haseolus, Ento JK (
Pisum), Solanum, Linum (L.
inuw), sweet potato (I pooaea), broad bean (Vicia), tobacco (N 1cotia)
na), Lycopersicon, Arachis, Brassica
ssica), Lactuca, Cucurbits and Cucurbits.
ita).

Man! L man and single full! -: Echinoch
loa), S etaria, P anicum, Mehishi t
P. tarii>, PhleuJ, PhleuJ, P. tarii>, P. tarii>, P. tarii>, Ph.
uca), E 1eusine, Brachiaria 13rachiaria, L.
olium), Sparrow/Bromus,
Oat fi (Avena), Cyperus R (Cy
perus), Sorghum (Sorgl+um), Agropyron (A gropyron), Dinoton (
Cynodon), Monochor
ia), F imbrisLylis,
S agittaria, E.
Ieocharis), S circu
s), Paspalum, I schaewum, I schaewum, S72/Claire (S
phenoc lea ), gucciroctenium ll
4 (D actyloctenium), Nukabo X (A
grostis), Sparrow gnome Jg (A Io
pecurus) and 7 Apera.

Big! 'p'1 Five Emperors J (lβ Oryza: Oryza
), Maize (Zea), Triticum (Tritium)
icum), barley (Hordeum), oat 14 (Avena), rye (S ecale)
, sorghum, pali
cum), Sugarcane (S accl+aru+s)
, 7 Ananas Jg, Ananas spp.
A sparagus) and Allium spp.

However, the use of the active compounds according to the invention is in no way restricted to these genera, but extends in the same way to other plants.

Depending on the concentration, the compounds can be used, for example, for the complete control of grass in industrial areas and on railway lines, on roads with or without trees and on squares.

The compound is suitable for perennial cultivation, such as silviculture, ornamental trees, orchards, vineyards, citrus groves, walnut orchards,
Banana plantations, coffee plantations, tea plantations, rubber tree plantations, oil palm plantations, cocoa plantations, small fruit tree plantings and hop cultivation plants, and for weed control in plants, and one hand It can be used for selective control of weeds in cultivated plants.

The active compounds according to the invention can be used, in particular in post-emergence treatments, for the selective control of weeds in monocotyledonous plants, such as corn, wheat and C/rice, and also in dicotyledonous plants, such as cotton and soybean. This new active compound is derived from corn,
It is clearly more active than the previously known compound, 2,4-biscyclopropylamino-5,6-cyclopyrimicine, while having comparable tolerance to both wheat and rice, cotton and soybeans. It is.

The active compounds can be used in the customary preparations, e.g. solutions, emulsions, wettable powders, suspensions, powders, dusting powders, pastes, soluble powders, granules, suspension-emulsifying concentrates, natural preparations impregnated with the active compound. and into microscopic capsules in synthetic and polymeric materials.

These formulations are prepared in the usual manner, for example by using the active compound with fillers, i.e. liquid solvents, and/or solid carriers, optionally with surfactants, i.e. emulsifiers and/or dispersants and/or blowing agents. You can do it.

When using water as extender, organic solvents can be used, for example as co-solvents. Suitable Q solvents include aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or aliphatic hydrocarbons such as chlorobenzene, chloroethylene or methylene chloride, Aliphatic hydrocarbons, such as cyclohexane, or paraffins, such as mineral oil fractions, mineral oils and vegetable oils, alcohols such as pig/
-ols or glycols and their ethers and esters, ketones such as 7setone, methyl ethyl ketone, methyl imbutyl ketone or cyclohexanone, highly polar solvents such as dimethylformamide and dimethylphoxate, and water.

Suitable solid carriers include, for example, ammonium salts and ground natural minerals such as kaolin, clay, talc,
Suitable solid carriers for granules include chite, quartz, akpaltzite, montmorillonite, or diatomite, and ground artificial minerals such as highly dispersed silicic acid, alumina, and silicates; suitable as solid carriers for granules include ground and classified natural Rocks, such as limestone, marble, pumice, sepiolite and dolomite, as well as inorganic and organic ground artificial particles and particles of organic substances, such as sawdust,
There are palm husks, corncobs and tobacco stalks.

Suitable emulsifiers and/or foaming agents include, for example, nonionic and 7-ionic emulsifiers, such as polyoxyethylene-fatty acid esters, polyoxyethylene-jl
Fatty flucol ethers, such as alkylaryl polyglycol ethers, alkyl sulfonates, furkyl sulfates, 7-lyl sulfonates, and fulpmin hydrolysis products, suitable as dispersants include, for example, geninsul 77 There are strike waste liquid and methyl cellulose.

#rAdhesives such as carboxymethyl cellulose and natural and synthetic polymers such as gum arabic, polyvinyl alcohol and polyvinyl acetate in powdered, granular or latex form and natural phospholipids such as cephalin and lecithin, and synthetic phospholipids may be used in the composition. can. Additionally, mineral and vegetable oils can be added.

Colorants such as inorganic pigments such as iron oxide, titanium oxide and 1
Prussian blue as well as organic dyes such as 7-litherin dyes and metal phthalocyanine dyes, and trace amounts of nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.

The preparations generally contain between 0.1 and 95% by weight, preferably between 0.5 and 90% by weight of active compound.

The active compounds according to the invention can also be used for controlling weeds, either as such or in the form of their preparations, in mixtures with known herbicides, finished formulations or seed mixtures being possible.

When used for herbicidal purposes, compounds that can be used as partners in the above mixtures include urea (for example metabenzthiazuron); diphenyl ether, acetanilide (for example alachlor and metolachlor).
metolachlor) G phenoxyalkane carboxylic acid (e.g. 2.4-D, 2,4-D, P, MCPA
SMCPP, and derivatives thereof); aryloxy-
and heteroaryloxy-phenoxy-propionic acids such as trimethylsilylmethyl-2-[4-(3,5
-dichloro-2-pyridyloxy)-phenoxy]-propione-); (2,2-noethoxy)-dityl 2-
(4-(3,5-dichloro-2-pyridyloxy)-phenoxy 1-propionate, (2-benoloxy)
-ethyl 2-(4-(3,5-dichloro-2-pyridyloxy)-72/xy)-propionate; triazines (e.g. metribuzin and 4-7minor 6-tert-butyl-3-ethylthio- 1,
2,4-tri7syn-5(4H)-one); triazinediones (e.g. ametridione); cyclohexanedione (e.g. sethoxydia+)
); benzonitrile (e.g. ioxynyl
nil)) and pentazone.

Other known active compounds, such as fungicidal fungicides,
Mixtures with insecticides, acaricides, nematicides, avicicides, phytonutrients and soil structure improvers are also possible.6 The active compounds may be used as such or in the form of their preparations. Usage forms prepared by further diluting, such as solutions, suspensions, emulsions, powders, which can be used immediately as they are;
It can be used as a coating agent and a granule. These dosage forms can be prepared by conventional methods such as irrigation, liquid spraying, atomizing or scattering.
ring).

The active compounds according to the invention can be applied to the plants either before or after emergence. It is also possible to add it to the soil and treat it before sowing.

The amount of active compound used can vary within a considerable range. The amount is determined essentially by the nature of the desired effect. Generally used amount is 0.0 per hectare
1 to 15 Kg, preferably 0.05 to 1 hectare
There is 10Kg''t'.

The preparation and use of the active compounds of the invention are illustrated below in the Examples.

Preparation Examples Example 1 48 g (0.54 mol) of 3-7 toxybrobylamine are dissolved in 50 g (0.27 mol) of 2.4.6-)lichloropyriminone in 300 mf of tetrahydro7ran. Add dropwise to the solution at -30°C. The reaction mixture is allowed to come to room temperature, stirred for a further 6 hours, poured into ice water and extracted with methylene chloride, the extracts are dried over sodium sulfate and the solvent is removed.

The residue obtained is subjected to steam distillation to obtain 10.6 [1 (16.6% of theory) of the desired pyrimidine as a solid with a melting point of 48°C.

b4-amino-6-chloro-2-3-methoxypropylamino)-virimicin fiS2 stage 10 g (0,04
2 mol) of 4,6-nochloro-2-(3-methoxy-probylamino)-pyrimidine are dissolved in 100 ml of dioxane and an aqueous ammonia solution of 60II11 is added.

The reaction mixture is heated to boiling for 4 hours, then mixed with 11 ice water and extracted with methylene chloride. The extract is dried over sulfuric acid, concentrated and the residue is boiled with white spirit, ovened and dried. 5,
6 g (61.6% of theory) of the desired pyrimidine, melting point 141° C., are obtained.

Example 2 5 g (0,025 mol) of 4-7 minnow 2,5-difluoro-6-dolifluoromethylpyriminone was added to 15011
11 dissolved in dioxane. 2.9 g (0,025 mol) of 3-impropoxyprobylamine and 2.5 g
(0,025 mol) of triethylamine was added dropwise thereto and the reaction mixture was heated to boiling for 5 hours.

After cooling and pouring into ice water with stirring, the resulting solid was furnaced, dried, and recrystallized from white spirit.

4 g (54% of theory) of the target pyrimidine having a melting point of 87"C are obtained.

Example 3 '+1 1.850g (9.31 mol) of 4-7 minnows 2.5t
6-Dolichlorobilimicin 4j! of tetrahydro7ran. 1.659g (18,62mol) of 3
-Methoxypropylamine is added dropwise thereto over 6 hours. The reaction mixture is heated to boiling for 5 hours, cooled and poured into 201ml of water with stirring. The resulting solid was oven-filtered, dried, stirred with 71 methymene chloride, and separated again.

The solid thus obtained is recrystallized twice from toluene to obtain 743 g (31.8% of theory) of the desired pyrimidine having a melting point of 114 DEG C.

Example 4 6.5. 120 ml of (0,033 mol) of 4-amino/-2,5,6-)lichloropyrimicin
) into the toluene solution in succession and the resulting mixture is heated to boiling for 5 hours. Once cooled, the reaction mixture is washed with water, the organic phase is dried over +7 um of sulfuric acid and concentrated. The crude product thus obtained was subjected to silica gel chromatography (column length 80 cm).

ethyl acetate and petroleum ether (1:
1). 4-7 minnow 6-(3-methoxy-1-methylpropylamino)-2,5-dichloropyrimicine (11th minute, melting point 62°C) plus 1.5
g (17.2% of theory) (second fraction, melting point 96° C.) of the desired pyrimidine are obtained.

The derivatives of general formula (I) listed in Table 1 below can be prepared in a similar manner.

Red (continued) 18. F. F. CH.

19 F 0CzHs CH3
20ClClCH.

21 F CF3 CH3
22F CF2 CH.

23 F CF3 Czl
h24 CI CHCl, CH.

25　　CI　CHCl□　　　　C2H.

26 CI CHCl□ C=H7(
i) 27 CI CHCl□ CH.

28 ClCF3 CH329C
I CF, C2H530CI
CF3 C3H? (1) 3IC
ICF, CH.

32 ClCl CH3H-C
H-(CH2), -OCH.

H-CH-(CHzh-0 0H.

H-CH-(CH2b-S cloudy CH.

H-(CH2), -0 melting point 98°C H-CH-(CHz)i-0 melting point 95-97°C CH.

H-(CH2), -OH H-(CH2)3- 0 Melting point 112-114
°CH-(CH2)3-O H-(CH2), -0 melting, α80°C H-CH-(CHz)z-0 0H.

H-(CH,), -OH-(CH2)s-O H-(CH,), -OH-CH-(CHt)z-0 CH3 H-CHt-CH-CHz-OJ: 1.5478C =H
y(i)! U (continued) 33 ClCl CH, H34
ClCl CH, H35CI C
I-(CH2)4CH3H36C
ICI-(CHz)scHs
H37ClCl CH3H3
8CI CI -CH2CH(C
H3)2 839 CI CI
-C,H*(t) H40ClCl
CH3CH341ClCl
CH3H42C1-CH,CI
CH3H-CH2.CH-CH2-0 melting point 86°C CH.

-(Ct-fz)as melting point 88℃-(CHz),
-0 melting point 37°C -(CH,), -0 melting point 45°C -(CHz)s-CH-Ont? : 1, 5680
0H.

-(CH2), -0 melting point 72℃ -(CH,), -0 melting point 80°C -(cH2)i-s Melting point 108℃ CH.

-C-CH,-0 CH.

-CH-(CH, h-0 melting point 110°C CH2 1J['' Formulas (If-1) to (II-8) used as starting materials
Halodenopyriminone and its production method are known.

Otherwise, the same compounds can be obtained analogously to those described for known compounds.

-565~ The 7-minobiliminones of HV-1) to ([5) used as starting materials and the methods for their production are known.6 Otherwise, these compounds can be prepared using methods similar to those described for known compounds. You can get it in this way.

EXAMPLES OF USE In the following examples, the compounds shown below were used as comparative substances.

(DE-O3 (German Patent Publication Specification) No. 2,630
．． No. 140, Example 12) Example A Post-emergence test Solvent: 5 parts by weight of a7tone emulsifier: 1 part by weight of alkylaryl polyglycol ether To prepare a suitable formulation of the active compound, 1 part by weight of Part of the active compound is mixed with the above-mentioned amount of solvent, the above-mentioned amount of emulsifier is added and the stock solution obtained is diluted with water to the desired concentration.

Test plants with a height of 5 to 150 I11 are sprayed with the preparation of the active compound in such a way that the desired amount of active compound is applied per unit area. The concentration of the spray solution is selected such that the desired amount of active compound is applied to 1) 20,001 liters of water per hectare. After 3 weeks, the degree of plant damage was expressed in % compared to the damage of untreated controls.

This number is 0% = no effect, same as untreated control) 100% = total plant death

Claims (1)

[Claims] 1. General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) In the formula, R^1 represents hydrogen or halogen, and R^2 may be substituted with halogen at any time. represents alkyl or represents halogen or alkoxy, R^3 represents alkyl, R^4 represents hydrogen or alkyl, Y represents oxygen or sulfur, and Z represents alkylene, branched or unbranched. 2,4-diaminopyrimidines. 2. In the general formula (I), R^1 represents hydrogen, chlorine, or fluorine, and R^2 is chlorine, fluorine, alkoxy having 1 to 6 carbon atoms, or optionally substituted with chlorine and/or fluorine. R^3 represents alkyl having 1 to 6 carbon atoms, R^4 represents hydrogen or alkyl having 1 to 6 carbon atoms, which may optionally be Pyrimidine derivatives according to claim 1, characterized in that Y represents oxygen or sulfur and Z represents branched or unbranched alkylene having 2 to 10 carbon atoms. 3. 4-amino-2-(3-
methoxypropylamino)-5,6-dichloropyrimidine. 4. 4-amino-2-(3-
Methoxy-1-methylpropylamino-5,6-dichloropyrimidine. 5. (A) General formula (II) ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (II) In the formula, R^1 and R^2 have the above-mentioned meanings, and X is halogen (preferably fluorine or chlorine). ) represents the halogenopyrimidine represented by the formula (III) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (III) In the formula, R^3, R^4, Y and Z have the above-mentioned meanings, and the amine and acid By reacting in the presence of a binder and, if appropriate, a diluent, the general formulas (IVa) and (IVb) ▲Mathematical formulas, chemical formulas, tables, etc.▼(IVa) + ▲Mathematical formula,
There are chemical formulas, tables, etc. ▼ (IVb) In the formula, R^1, R^2, R^3, R^4, X, Y and Z have the above-mentioned meanings. 1 step), then the above two isomers are separated and the pyrimidine derivative of formula (VIa) is treated in a further subsequent reaction step with ammonia (V) and NH_3(V) in the presence of an acid acceptor and if appropriate If so, either react in the presence of a diluent to give the pyrimidine derivative of formula (I) (second step), or (B) General formula (VI) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(VI) Formula A 4-aminopyrimidine derivative in which R^1, R^2 and ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) In the formula, R^1, R^2, R^3, R^4, Y and Z have the above-mentioned meanings, giving a pyrimidine derivative of, and R^ When 2 represents a halogen, the desired pyrimidine derivatives of the general formula (I) are the obtained formulas (I) and (I a) ▲ Mathematical formulas, chemical formulas, tables, etc. etc. ▼ (I a) characterized in that it is isolated from an isomeric mixture of pyrimidine derivatives in which R^1, R^2, R^3, R^4, X, Y and Z have the meanings given above. 2 of formula (I) described in claim 1,
Method for producing 4-diaminopyrimidines. 6. 2 of the general formula (I) described in claim 1,
A herbicide characterized by containing at least one type of 4-diaminopyrimidine. 7. 2 of general formula (I) described in claim 1,
Use of 4-diaminopyrimidine for controlling harmful plants. 8. 2 of the general formula (I) described in claim 1,
A method for producing a herbicide, which comprises mixing 4-diaminopyrimidine with a filler and/or a surfactant.