JPH04112876A - Pyrimidine or triazine derivative and herbicide - Google Patents

Abstract

NEW MATERIAL:A pyrimidine or triazine derivative expressed by formula I (R<1> is H, lower alkyl, lower alkenylbenzyl, 2-trimethylsilylethyl, etc.; R<2> and R<3> are halogen, lower alkyl, lower alkoxy, etc.; X is H, halogen, lower alkyl, lower alkoxy, nitro, amino, etc.; Y is O, S, NH or N-CHO; Z is N or methine) EXAMPLE:2-{(4,6-Dimethoxypyrimidin-2-yl)oxy}-6-phenylbenzoic acid benzyl ester. USE:A herbicide useful to paddy field, upland, tree garden, non-farm land, etc. PREPARATION:A compound expressed by formula II is reacted with a pyrimidine compound or triazine compound expressed by formula III (L is halogen, alkylsulfonyl, etc.) in the presence of a base, preferably in the temperature range of boiling point of a solvent to provide the compound expressed by formula I.

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a novel pyrimidine or triazine derivative and a herbicide containing the same that can be applied to paddy fields, fields, non-agricultural land, etc.

[Prior Art] The present applicant has already published Japanese Patent Application Laid-Open No. 1-250366. However, the herbicidal effects of the compounds described in the above-mentioned publication cannot necessarily be said to be sufficient. The present inventors conducted intensive research on pyrimidine or triazine compounds with the aim of developing further improved compounds, and as a result, the present inventors produced a pyrimidine or triazine derivative of the present invention in which a phenyl group was introduced in place of a phenoxy group on the benzene ring. The present invention has been completed based on the discovery that the compound exhibits a superior herbicidal effect, especially against grass weeds, compared to the compounds described in the specifications of the above-mentioned publications.

[Means for Solving the Problems] The pyrimidine or triazine derivative of the present invention has the following properties:
n represents an integer of 0 or 1 or 2. ) has been found to have herbicidal activity.

[Problems to be Solved by the Invention] (In the formula, R' is a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a benzyl group, an alkoxyalkyl group, a 2-trimethylsilylethyl group, a 2-trimethylsilylethoxymethyl group) , represents an alkali metal, alkaline earth metal or organic amine cation, R', R
' are the same or different and represent a halogen atom, a lower alkyl group, a lower alkoxy group, or a difluoromethoxy group; It represents a fluoromethyl group, Y represents an oxygen atom, a sulfur atom, an NH group or an N-C84 group, and Z represents a nitrogen atom or a methine group. ).

Next, the compounds of the present invention represented by formula [1] are illustrated in Tables 1 to 4. In addition, the compound number will be referred to in the following description.

(Margin below) Table 1 continued Table 1 continued [A]: CH, QC, H, 5i (CH,), [B]
・3.5-(CF, ),,[C]=2.3-(-C
H=C)l-CH=CH-), [DconiN-CH
In addition, the intermediates of the metal products of the present invention represented by the following general formula [[] are also recognized to have excellent physiological activity.

(In the formula, X.

(Y has the same meaning as above) Representative examples are as follows.

Intermediate 1 (refractive index n p'''l, 5212) Intermediate 2 (refractive index n ''p' ・1.536 '') The compound of the present invention can be produced according to the following methods, but is not limited to these methods. It is not something that will be done.

<Method A> The compound of the present invention represented by 2[1] is prepared by combining the compound represented by the formula [[] and the pyrimidine compound or triazine compound represented by the formula [I[1]] in the presence of a base, preferably at the boiling point of the solvent. It can be produced by reacting within the temperature range of .

[Itl [IIl]
[+] (In the formula, R゛, R゛, R゛, x, Y, and Z represent the same meanings as above, and L represents a halogen atom, an alkylsulfonyl group, a pencilsulfonyl group, or a substituted benzylsulfonyl group.) Examples of the base used here include alkali metals such as sodium metal and potassium metal, alkali metal hydrides and alkaline earth metal hydrides such as sodium hydride, potassium hydride, and calcium hydride, sodium carbonate,
Carbonates such as potassium carbonate and calcium carbonate, and sodium hydrogen carbonate.

Bicarbonates such as potassium bicarbonate, sodium hydroxide,
Examples include alkali metal hydroxides such as potassium hydroxide, organic acid salts such as potassium acetate, and alcoholades such as sodium methylate. Furthermore, organic bases such as pyridine and triethylamine can also be used.

In addition, the solvents used include hydrocarbon solvents such as benzene and toluene, halogenated hydrocarbon solvents such as methylene chloride and chloroform, alcohol solvents such as ethanol and methanol, diethyl ether, tetrahydrofuran, 1,2 - Ether solvents such as dimethoxyethane, aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and dimethyl sulfoxide, ester solvents such as ethyl acetate, and ketones such as acetone and methyl ethyl ketone. Examples include solvents. When the reaction is carried out without a solvent, an alkali metal carbonate such as anhydrous potassium carbonate is used as the base.
It is also possible to carry out the reaction within a temperature range of 120-160°C.

Among the compounds of formula []] used here, X and R″
6-phenylsalicylic acid in which is a hydrogen atom and Y is an oxygen atom is Annalen der
Chemie) Vol. 594, pp. 137-158 (195
It is known that the compound can be produced by the method described in 1995), but since the method described in this literature produces by-products with different substitution positions, in the present invention, it was produced by the following reaction formula.

Examples include aprotic polar solvents such as rusulfoxide, ester solvents such as ethyl acetate, ketone solvents such as acetone and methyl ethyl ketone, and acetonitrile.

Furthermore, among the compounds represented by the formula [rV], a compound in which Y is a sulfur atom can be produced by the following method.

[rV] [V] [
II] (In the formula, R゛, X, Y represent the same meanings as above, and R
4 represents a halogen atom. ) Examples of the base used include carbonates such as sodium carbonate, bicarbonates such as sodium bicarbonate, and organic amines such as triethylamine and pyridine. Solvents used include hydrocarbon solvents such as benzene and toluene, alcohol solvents such as ethanol and methanol, ether solvents such as ethyl ether, tetrahydrofuran, and 1,2-dimethoxyethane, and N,N-dimethyl. Formamide, N,N-dimethylacetamide, dimethy(in the formula, R゛, R4 represent the same meanings as above), and also the formula [V
] The phenyl oxalate compound represented by
f Organic Chemistry) Volume 49,
20, pp. 5237-5243 (1984).

Method> Particularly, the compound of the present invention in which R is hydrogen in the -formula [+],
As shown in the reaction formula below, a compound of the general formula [■J in which R′ corresponds to a benzyl group, for example, Raney nickel,
It can be produced by catalytic hydrogen reduction in the presence of a catalyst such as palladium on carbon.

I can do it. It can be produced by treating a compound of the general formula [1] in which R" corresponds to a 2-(trimethylsilyl)ethyl group or a 2-(trimethylsilyl)ethoxymethyl group with a fluorine reagent.

(In the formula, X, Y, Z, R', and Ro represent the same meanings as above.) The solvents used here include water, hydrocarbon solvents such as benzene and toluene, and alcohol solvents such as ethanol and methanol. Solvent, ethereal solvent such as diethyl ether, tetrahydrofuran, 1,2-dimethoxyethane,
Furthermore, ester solvents such as ethyl acetate and methyl acetate,
Examples include ketone solvents such as acetone and methyl ethyl ketone, and acetic acid.

<Method C> Furthermore, the compound of the present invention in which R is hydrogen in the general formula [I] can also be produced by the following method (in the formula, X, Y,
Z, R', and Ro represent the same meanings as above, and Ro is 2
-(trimethylsilyl)ethyl group or 2-(trimethylsilyl)ethoxymethyl group. ) Examples of the fluorine reagent used here include quaternary ammonium fluoride compounds such as tributylammonium fluoride, or alkali metal fluorides such as potassium fluoride and cesium fluoride. Further, as the solvent used, the same solvent as in Method A can be used.

<Method D> In addition, the compound of the present invention in which R" in the general formula [1] represents a cation such as an alkali metal, an alkaline earth metal, or an organic amine, can be prepared, for example, by the general formula [C method].
+] in which Ro is a hydrogen atom and a base within the boiling point of the solvent.

(In the formula, X, Y, Z, R'', and Ro represent the same meanings as above. M is an alkali metal such as sodium or potassium,
Indicates alkaline earth metals such as calcium and cations of organic amines. ) Bases used here include, for example, alkali metals such as sodium metal and potassium metal, alkali metal hydrides and alkaline earth metal hydrides such as sodium hydride, potassium hydride, and calcium hydride, sodium carbonate,
Carbonates such as potassium carbonate and calcium carbonate, and alkali metal hydroxides such as sodium hydroxide and potassium hydroxide can be used.

Furthermore, examples of the organic base include ammonia, monoalkylamines such as methylamine, dialkylamines such as dimethylamine, trialkylamines such as triethylamine, and aromatic amines such as pyridine.

Solvents used here include water, hydrocarbon solvents such as benzene and toluene, halogenated hydrocarbon solvents such as methylene chloride and chloroform, alcohol solvents such as ethanol and methanol, diethyl ether, tetrahydrofuran, Examples include ether solvents such as 1.2 dimethoxyethane and 1,4-dioxane, ester solvents such as ethyl acetate, ketone solvents such as acetone and methyl ethyl ketone, and acetonitrile.

<Method E> Additionally, in the general formula [11, R'' is a lower alkyl group, a lower alkenyl group, a lower alkynyl group, an alkoxyalkyl group,
The compound of the present invention representing a 2-(trimethylsilyl)ethoxymethyl group can be prepared by, for example, preparing a compound of the general formula [1] in which R" is a hydrogen atom, which is produced by <Method C>, in the presence of an appropriate base, at a temperature below the boiling point of the solvent. It can be produced by reacting within a certain range.

(In the formula, X, Y, Z, R', R', R' and L represent the same meanings as above.) Examples of the base used here include alkali metals such as metallic sodium and metallic potassium, hydrogen Alkali metal hydrides such as sodium chloride and potassium hydride, carbonates such as sodium carbonate and potassium carbonate, bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate, organic bases such as trimethylamine, pyridine, N,N-diisopropylethylamine, etc. types can be used.

Solvents used here include hydrocarbon solvents such as benzene and toluene, ether solvents such as diethyl ether, tetrahydrofuran, 1,2-dimethoxyethane, and 1,4-dioxane, and ethyl acetate. ester solvents, ketone solvents such as acetone and methyl ethyl ketone, halogen solvents such as dichloromethane and chloroform, and acetonitrile.

Next, the method for producing the compounds and intermediates of the present invention will be specifically explained with reference to Reference Examples and Examples.

Example 1 2-((4,6-cymethoxypyrimidin-2-yl)
Benzyl oxy)-6-phenylbenzoate (compound l)
Synthesis of benzyl 6-phenylsalicylate (0.9 g, 3 mM) and 4,6-simethoxy-2-methanesulfonylpyrimidine (0.6 g, 3 mM) in a 50 mQ capacity eggplant flask.
, potassium carbonate (0.5g, 3.5mM) and N,N-
Dimethylformamide (hereinafter abbreviated as DMF, 10mfi)
) and reacted at 80°C for 1 hour. After cooling the reaction mixture, DMF was distilled off under reduced pressure, and the resulting residue was dissolved in ethyl acetate, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated. The obtained residue was purified by column chromatography to obtain 1.2 g of the target compound as a colorless transparent viscous liquid (yield: 92.3%).

Example 2 2-((4,6-dimethoxypyrimidin-2-yl)
Synthesis of oxy)-6-phenylbenzoic acid (compound 3) Benzyl 2-((4,6-cymethoxypyrimidin-2-yl)oxy)-6-phenylsalicylate (1.1 g, 2゜5mM) 10%-
Palladium on carbon (0, Ig) and methanol (20ml
2) was added and hydrogen was blown into the tank. After consuming the required amount of hydrogen, the palladium on carbon was filtered off. Methanol was distilled off under reduced pressure, and the residue was dissolved in toluene, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated. The obtained residue was crystallized in hexane to obtain the target compound 0 as a white powder.
．． 5 g was obtained (yield 62.5%).

Example 3 Synthesis of (2-trimethylsilyl)ethyl 2-((4,6-dimethoxybilimicin-2yl)oxy)-6-(4-methylphenyl)benzoate (compound 23). -(4-methylphenyl)(2-trimethylsilyl)ethyl salicylate (3,
2g, 9.7mM), 4,6-simethoxy-2-methanesulfonylpyrimidine (2.0g, 9.2mM), potassium carbonate (1.3g, 9.4mM) and DMF (20
mg) and reacted at 80°C for 1 hour. After cooling the reaction mixture, DMF was distilled off under reduced pressure, and the resulting residue was dissolved in ethyl acetate, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated. The obtained residue was purified by column chromatography to obtain 3.1 g of the target compound as an orange transparent viscous liquid (yield 7262%).

Example 4 2-((4,6-dimethoxypyrimidin-2-yl)
Synthesis of oxy)-6-(4-methylphenyl)benzoic acid (compound 24) In a 50rr+C capacity eggplant flask, add 2'-1(4,6cymethoxypyrimidin-2-yl)oxy)6-(4-methyl (2-trimethylsilyl)ethyl (phenyl)benzoate (2.6 g, 5.6 mM) was dissolved in tetrahydrofuran (
Tetrabutylammonium fluoride hydrate (3.5 g, 13.3 mM) was added portionwise. After stirring at room temperature for 2 hours, tetrahydrofuran was distilled off under reduced pressure. Add water to the resulting residue,
The pH was adjusted to 3 with 10% hydrochloric acid, and then extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated. The obtained residue was crystallized in hexane with water cooling to obtain the target compound 2.0 as an ocher semi-solid substance.
g (yield 95.2%).

Example 5 2-((4,6-cymethoxypyrimidin-2-yl)
2-+ (4,6-
cymethoxypyrimidin-2-yl)oxy+ -6-(
4-methylphenyl)benzoic acid was dissolved in DMF (15 mQ) and added in small portions. After stirring was continued until hydrogen evolution stopped, methyl iodide (0.7g, 5mM) was added, the mixture was allowed to react at room temperature for 2 hours, and the mixture was poured into ice water. This was extracted with ethyl acetate, washed with water, a 5% aqueous sodium bicarbonate solution, and saturated brine, dried over anhydrous sodium sulfate, and concentrated. The obtained residue was purified by column chromatography and crystallized in hexane to obtain 0.8 g of the target compound as an ocher powder (yield 57.1%).

Reference Example 1 Synthesis of 2-trimethylsilylethyl 6-(4-methylphenyl)salicylate (Intermediate 2) Tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.52 mM) was added to a 200 mΩ capacity 3-day flask. 6-bu0-
E 2-trimethylsilylethyl salicylate (3.2g,
10°OmM) and 1,2-dimethoxyethane (40mM
Q) was added and stirred for 10 minutes under a nitrogen stream. 4-methylphenyl fluoric acid (2.0g, 15.0mM)
It was dissolved in dimethoxyethane (40rr+Q) and added, and stirring was continued for an additional 10 minutes. A 2M aqueous sodium carbonate solution (40ml (1) was added and reacted at 70-80°C for 10 minutes, then cooled to room temperature and poured into ice water.1
The pH was adjusted to 1 with 0% hydrochloric acid, extracted with ethyl acetate, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated.

The obtained residue was purified by column chromatography to obtain 3.2 g of the target compound as a yellow transparent liquid (yield 97.
0%).

(The following is a blank space) The herbicide of the present invention contains a pyrimidine or triazine derivative represented by the formula [I] and a salt thereof as an active ingredient.

When the compound of the present invention is used as a herbicide in rice fields, fields, orchards, non-agricultural lands, etc., the active ingredient can be used in an appropriate dosage form depending on the purpose.

In normal cases, the active ingredient is diluted with an inert liquid or solid carrier, and if necessary, surfactants, dispersants, adjuvants, etc. are added to form powders, wettable powders, emulsions, granules, etc. It can be formulated and used in various forms. Examples of carriers used in formulation include solid carriers such as dicrite, talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate, and urea, isopropyl alcohol, xylene, cyclohexanone, and methylnaphthalene. Examples include liquid carriers such as . Examples of surfactants and dispersants include alcohol sulfate salts, alkylaryl sulfonates, lignin sulfonates, polyoxyethylene glycol ethers, polyoxyethylene alkylaryl ethers, and polyoxyethylene sorbitan monoalkylates. . Examples of the adjuvant include carboxymethyl cellulose, polyethylene glycol, gum arabic, and the like. When using it, it can be diluted to an appropriate concentration and sprayed, or it can be applied directly. The active ingredient of the compound of the present invention is applied in an amount of 0.1 g to 1 kg per 10 are.

In addition, the compound of the present invention may be used as an insecticide, fungicide, or
It may be used in combination with other herbicides, plant growth regulators, fertilizers, etc.

Next, the formulation method will be specifically explained using typical formulation examples. In the following description, "part" means part by weight.

Formulation Example 1 10 parts of wettable powder compound (27), 0.5 part of Emulgen (registered trademark of Kao Corporation) 810, 0.5 part of Demol (registered trademark of Kao Corporation) N, Kunilite (Kunimine Kogyo Co., Ltd.) Co., Ltd.'s registered trademark) 201, 20 copies, Seeklite (
A wettable powder was obtained by mixing and pulverizing 69 parts of CA (registered trademark of Zeekrite Co., Ltd.).

Formulation Example 2 10 parts of wettable powder compound (29), 0.5 part of Emulgesi 8]0, 0.5 part of Demol N, 20 parts of Kunilite 201,
5 parts of Carplex 80 and 64 parts of Zi-Glide CA are mixed and pulverized to obtain a wettable powder.

Formulation Example 3 To 30 parts of emulsion compound (3), 60 parts of a mixture of equal amounts of xylene and isophorone and 10 parts of surfactant Tsurupol (registered trademark of Toho Chemical Industry Co., Ltd.) 800A are added, and these are thoroughly stirred to form an emulsion. get.

Formulation Example 4 10 parts of granule compound (lO), 1 = talc and bentonite
80 parts of bulking agent mixed in a ratio of 3 parts, 5 parts of white carbon, 5 parts of surfactant Tsurupol 800A and 1 part of water.
Add 0 parts and knead well to make a paste with a diameter of 0.
．． After extruding through a 7mm sieve hole and drying, 0.5
Cut into lengths of ~1 mm to obtain granules.

[58 Effect of light] The compound of the present invention represented by the general formula [I] and its salt,
Annual weeds that occur in rice fields, such as Japanese grasshopper, Japanese cypress, and Japanese cypress;
It exhibits excellent herbicidal effects at an extremely low dose over a wide range of perennial weeds such as firefly and grasshopper, from the time of germination to the growing season. In addition, there are various weeds that can be a problem in fields, including broad-leaved weeds such as Japanese knotweed, Japanese knotweed, whiteweed, chickweed, Japanese chickweed, Japanese goldenrod, morning glory, and Japanese fir tree, as well as perennial weeds such as Japanese knotweed, Japanese yellowtail, Japanese cypress, Japanese cyperus, and Japanese cyperus. It is possible to effectively control grass weeds such as young Cyperaceae weeds, barnyard grass, grasshopper, foxtail grass, sycamore grass, johnson grass, grasshopper grass, and wild oat. Applicable crops include sugarcane, pineapple, etc. in addition to common Japanese vegetables and fruit trees. Furthermore, kudzu, which is a problem weed in non-agricultural land,
It also has an excellent herbicidal effect on pampas grass, horsetail, bamboo grass, reed, mugwort, Japanese knotweed, Japanese knotweed, Japanese wattle, Japanese dandelion, etc. It can also be used in forest areas such as cedar and cypress. The herbicide of the present invention has an excellent herbicidal effect particularly on grasses such as barnyard grass and johnson grass, compared to the compounds described in the above-mentioned publications.

Next, the effects of the compounds of the present invention will be explained by giving test examples.

Test example 1 (herbicidal effect test by paddy soil treatment) 100
A cm' plastic pot was filled with paddy soil, and after puddling, seeds of Japanese millet (Ec), Japanese snail (Mo), and scallop (Sc) were sown, and the pot was submerged in water to a depth of 3 cm. The next day, the wettable powder prepared according to Formulation Example 1 was diluted with water and dropped onto the water surface. The application amount was 100 g of active ingredient per 10 ares. After that, it was grown in a greenhouse and processed 21
On the following day, the herbicidal effect was investigated according to the standards in Table 5. The results are shown in Table 6.

Table 5 Index herbicidal effect (degree of growth inhibition) Table 6 Table 7 Table 6 continued Test example 2 (herbicidal effect test by field soil treatment) 100c
m” plastic pots were filled with field soil and planted with edible cottontails (Ec), Japanese knotweed (PO), bluetails (Am),
Seeds of Shiroza japonica (Ch) and Cyperus japonica (Ci) were sown and covered with soil. A wettable powder prepared according to Formulation Example 1 was diluted with water, and an amount equivalent to 100 Q per 10 are was uniformly sprayed on the soil surface using a small sprayer so that the active ingredient was 100 g per 10 are.

Thereafter, the plants were grown in a greenhouse, and the herbicidal effect was investigated according to the standards in Table 5 on day 20 of treatment. The results are shown in Table 7.

Test Example 3 (Herbicidal effect test by field soil stem and leaf treatment) 100
cm'' plastic pots were filled with field soil and planted with edible cottontails (Ec), Japanese knotweed (Po), and bluetails (Am).
, Shiroza (Ch), and Kogomega Yatsuri seeds were sown and covered with soil. After growing in a greenhouse for 2 weeks, the wettable powder prepared according to Formulation Example 1 was diluted with water, and the active ingredient per 10.
An amount equivalent to 10 (liters) per 100 g was sprayed on the entire plant from above using a small sprayer.

Thereafter, the plants were grown in a greenhouse, and the herbicidal effect was investigated according to the standards in Table 5 on day 14 of treatment. The results are shown in Table 8.

Table 8 (Continued from Table 8) Gao (lp) and Japanese staghorn (Xa) were sown, and tubers of Japanese sedge (Cr) were placed on the bed and covered with soil. A predetermined amount of active ingredient of an aquarium prepared according to Formulation Example 1 was diluted with water, and 10
An amount equivalent to 100Q per area was uniformly sprayed on the soil surface using a small sprayer. Thereafter, the plants were grown in a greenhouse, and the herbicidal effect was investigated according to the standards in Table 5 for 20 days of treatment. The test results are shown in Table 9.

In addition, the following compound described in the specification of JP-A-1-250366 was used as a comparative drug.

Comparative compound (A) Test example 4 (herbicidal effect test at a low dose by treating field soil) A 600 cm' plastic pot was filled with field soil,
Japanese barnyard grass (Ec), johnson grass (So), Japanese knotweed (PO), Japanese violet (Am), Japanese staghorn grass (Ch), Noasagao (Ip) and Japanese fir tree (Xa) were sown, and the comparison compound (B) was added to Table 9. It is shown in Table 10.

Note that the same compound as in Test Example 4 was used as the comparative drug.

Test Example 5 (Herbicidal effect test at low dosage by field soil foliage treatment) A 600cm' plastic pot was filled with field soil,
Japanese barnyard grass (Ec), johnson grass (SO), Japanese knotweed (Po), Japanese violet (Am), whiteweed (Ch), and white gloat (Ip) were sown, and tubers of Japanese sedge (Cr) were placed on the bed and covered with soil. After growing in a greenhouse for two weeks, dilute the prescribed amount of active ingredients of the water conservancy prepared according to Formulation Example 1 with water,
An amount equivalent to 100 Q per 10 ares was sprayed onto the entire plant from above using a small sprayer.

Thereafter, the plants were grown in a greenhouse, and the herbicidal effect was investigated according to the standards in Table 5 for a total of 14 days of treatment. As a result, Ihara Chemical Industry Co., Ltd.

Claims (2)

[Claims] (1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R^1 is a hydrogen atom, lower alkyl group, lower alkenyl group, lower alkynyl group, benzyl group, alkoxyalkyl group, 2-trimethylsilylethyl group , 2-trimethylsilylethoxymethyl group, alkali metal, alkaline earth metal or organic amine cation, R^2
, R^3 are the same or different and represent a halogen atom, a lower alkyl group, a lower alkoxy group or a difluoromethoxy group, and X is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a nitro group, an amino group, a cyano group. group or trifluoromethyl group, Y represents an oxygen atom, sulfur atom, NH group or N-CHO group, and Z represents a nitrogen atom or a methine group. ) Pyrimidine or triazine derivatives and salts thereof. (2) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R^1 is a hydrogen atom, lower alkyl group, lower alkenyl group, lower alkynyl group, benzyl group, alkoxyalkyl group, 2-trimethylsilylethyl group , 2-trimethylsilylethoxymethyl group, alkali metal, alkaline earth metal or organic amine cation, R^2
, R^3 are the same or different and represent a halogen atom, a lower alkyl group, a lower alkoxy group or a difluoromethoxy group, and X is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a nitro group, an amino group, a cyano group. group or trifluoromethyl group, Y represents an oxygen atom, sulfur atom, NH group or N-CHO group, and Z represents a nitrogen atom or a methine group. ) Herbicides containing pyrimidine or triazine derivatives and their salts as active ingredients.