JPH01207205A - Agricultural chemical composition - Google Patents

Abstract

PURPOSE:To obtain the above composition storable without causing isomerization reaction of the active component, free from toxicity to crops, human and animals and effective against Helminthosporium leaf spot, etc., by using a pyrimidine derivative and an oxide or hydroxide of a specific metal as active components. CONSTITUTION:The objective composition contains (A) a pyrimidine derivative of formula (Ar is phenyl substituted with lower alkyl; R1, R2 and R3 are lower alkyl) or its salt and (B) oxide or hydroxide of zinc, calcium or magnesium as active components. It is preferable for the sufficient suppression of the isomerization reaction to add an aliphatic amine compound or a diamine compound to the composition. The amount of the amine is preferably about 0.1-5 pts.wt. in the agricultural chemical preparation. The amount of the compound of formula is preferably about 0.0001-50 pts.wt., for dust formulation and about 10-90 pts.wt. for wettable powder and sol formulation based on 100 pts.wt. of the composition.

Description

[Detailed description of the invention] Industrial applications The present invention relates to stabilized agrochemical compositions.

More specifically, the present invention relates to a stabilized agricultural chemical composition containing a pyrimidine derivative represented by the following general formula CI, which has excellent control and treatment effects on blight, sesame leaf blight, and the like.

A pyrimidine derivative (hereinafter abbreviated as compound M) represented by the conventional technical formula [wherein, Ar is a phenyl group substituted with a lower alkyl group, and R1, Rt and R5 are lower alkyl groups].

) is a compound that is useful as a fungicide for agricultural and horticultural purposes, and is effective in controlling pests such as rice blast, sesame leaf blight, and micrococcal kernel disease, as described in JP-A-55-151570.

Problems to be Solved by the Invention However, Compound M has a problem in that when it is formulated into a formulation, it undergoes an isomerization reaction under the influence of other ingredients.

In other words, compound M has a double bond between C-N, p.

On the other hand, there is an E form which is a geometric isomer represented by the formula, and both isomers can be isolated individually. Both isomers may also exist as a mixture in a certain equilibrium state. The equilibrium of the two forms may shift to the E form depending on other coexisting components and other conditions.

Therefore, when Compound M, which has two forms, is formulated, the E form may increase due to the influence of other coexisting components. However, the E form is less preferable than the 2 form from the standpoint of stability of the compound itself, and it is desirable to prevent isomerization from the 2 form to the E form.

In general, agrochemical active substances are often mixed with various carriers, auxiliary ingredients, etc., and formulated into various forms for practical use. Compound M is also used not only in preparations containing only Compound M as the agricultural active ingredient, but also as a mixture with other active ingredients for the purpose of labor-saving simultaneous control of pests and diseases. When formulated in this way, compound M often undergoes isomerization.

In particular, in the coexistence with acidic substances, isomerization to the E form is remarkable. As mentioned above, there is a great demand for mixtures of Compound M and various insecticides and fungicides, but many insecticides and fungicides are acidic substances or substances that are more stable in an acidic region. In addition, there are acidic substances among the auxiliary ingredients commonly used in formulation, and when compound M is mixed with these substances, compound M undergoes isomerization as in the past. Furthermore, some carriers promote isomerization to the E form.

Therefore, an object of the present invention is to prevent isomerization of Compound M in an agrochemical formulation containing Compound M. Furthermore, preferably, the isomerization of compound M is suppressed without adversely affecting other components, thereby providing a stabilized agrochemical composition.

Means for Solving the Problems The present inventors have conducted various studies in order to obtain a pesticide formulation containing Compound M that exhibits excellent medicinal efficacy in controlling rice blast, etc., and in which its isomerization is prevented. Surprisingly, it was discovered that the isomerization reaction of Compound M was suppressed when a specific metal oxide or hydroxide was added to such a preparation, and that there were no toxicity problems for crops or humans or livestock. After making this discovery and conducting further studies, we have completed the present invention.

That is, the present invention provides a pyrimidine derivative represented by the formula (1) [wherein Ar is a phenyl group substituted with a lower alkyl group, rt, , Rt and R3 do not represent a lower alkyl group] and (2) zinc. The present invention relates to a stabilized agricultural chemical composition characterized by containing an oxide or hydroxide of calcium or magnesium.

The agricultural chemical active ingredient compound M of the present invention is disclosed in Japanese Patent Application Laid-open No. 55
-151570.

Among the Z-form compounds M represented by formula (1), certain compounds (hereinafter sometimes abbreviated as compound M) and certain compounds (hereinafter sometimes abbreviated as compound M2) are suitable.

As the metal oxides or hydroxides used in the present invention, oxides or hydroxides of specific metals such as zinc, calcium, or magnesium represented by the formulas ZntO, ZnO, CaO, MgO, etc. are preferable.

Furthermore, these metal oxides may be used in the form of composite oxides of these metal oxides and oxides of other metals (eg, barium, aluminum, etc.) or 5iOz, etc. Examples of such composite oxide include ZnOA
lto, ZnO5iot.

Examples include ZnO-MgO.

These metal oxides (including their composite oxides) or metal hydroxides may be used alone, or two or more types may be used in combination.

For example, in a mixture of Compound M, which has an excellent control effect on blast disease, sesame leaf blight, etc., and Cartap hydrochloride, which has an excellent control effect on various insect pests, such as Japanese planthopper and planthopper, the above-mentioned metals are used. Among the oxides or hydroxides, oxides are more preferable because they have no adverse effect on cartap hydrochloride. Furthermore, in these various mixtures, zinc oxide generally does not affect other mixed active ingredients and has little adverse effect, therefore has an excellent stabilizing effect on the formulation, has a high isomerization prevention effect of Compound M, and has a high effect on crops. It is particularly suitable because of its low toxicity to humans and livestock.

The addition of the above-mentioned metal oxides or hydroxides or the above-mentioned composite oxides is not particularly limited;
It is effective to use about o, oot to 50 parts by weight, preferably about 0.1 to 20 parts by weight. usually,
The composition of the present invention contains the pyrimidine derivative represented by the general formula (1) or its salt, that is, the compound M and the above-mentioned metal oxide or hydroxide, as well as other agricultural chemical active substances and various carriers and auxiliary ingredients. Mixed with powder and hydrating agent 1
The dosage form is granules, sol, etc. Here, various surfactants (eg, lignin sulfonate, alkylbenzene sulfonate, polyoxyethylene alkyl ether) can be used as carriers or auxiliary components.

alkylnaphthalene sulfonate, etc.), dispersant (eg, ethylene glycol, glycerin, etc.), flow aid (eg, white carbon, etc.), and fixing agent.

Young absorbing agents, antioxidants (e.g. dibdelhydroxytoluene, 4,4-thiobis-6-tert-butyl-3-
methylphenol, etc.), preservatives (e.g. sorbic acid, potassium sorbate, etc.), synergists, wetting agents.

Stabilizers, solvents, excipients, diluents, suspending agents, spreading agents, penetrating agents, mucilage agents, etc. are included. Pesticide active substances other than compound M include sulfur-based, organic phosphorus-based, organic arsenic-based,
Disinfectants such as organic chlorine and organic phosphorus.

Examples include organochlorine-based, carbamate-based, pyrethroid-based insecticides and acaricides, and various antibiotics. More specifically, carriers and auxiliary ingredients include vegetable powders such as soybean flour, tobacco flour, wheat flour, and wood flour, and clays (kaolin, etc.).

bentonite, acid clay, etc.), talc (talcum powder).

In addition to mineral powders such as silica (diatomaceous earth, mica powder, etc.), solid carriers and auxiliary ingredients such as calcium carbonate, sulfur powder, and activated carbon are often used. Some examples of the above pesticide active substances include organic sulfur fungicides,
Organophosphorus fungicides such as ethylene bis(dithiocarbamic acid) zinc, ethylene bis(dithiocarbamic acid) manganese, ethylene bis(dithiocarbamic acid) ammonium, bis(dimethyldithiocarbamic acid) ethylene bis(dithiocarbamic acid) dizinc...thiophosphoric acid S-
Benzyl 0.0-diisopropyl, dithiophosphoric acid S,
Organic arsenic fungicides such as S-diphenyl 0-ethyl; base fungicides such as iron methanarsonate and ammonium iron methanarsonate; pentachlorophenol;

Other fungicides such as tetrachloroisophthalonitrile, 4,5,6,7-titrachlorophthalide, tridiclazole, N-(trichloromethylthio)-4-cyclohexene-I, 2-dicarboximide. Phenazine 5-oxide, l-(butylcarbamoyl)-2-benzimidazole carbamic acid Medyl and other atom-based insecticides...0.0-dimethyl 0-(3medyl-4-nitrophenylphosphorothioate (hereinafter referred to as (abbreviated as MEP), dithiophosphoric acid S-[1,2-
Bis(ethoxycarbonyl)ethyl]0.0-dimethyl, phosphoric acid 2.2-dichlorovinyl dimethyl, 2,2
．． 2-) Lichloro-1-hydroquinedylphosponic acid
Dimedyl, N-acetylphosphoramidodiolic acid 0
0S-dimethyl.

Dimethyl phosphate (E)-1-methyl-2-methylcarbamoyl vinyl, dithiophosphoric acid 0. O-dimethyl
Organochlorine insecticides such as S-[α-(ethoxycarbonyl)benzyl], didiophosphoric acid 0.0-dimethyl 5-(N-methylcarbamoylmethyl)...6,7,8,9,10.10-
Carbamate insecticides such as hexachloro-1,5,5a,6,9.9a-hexahydro-6,9-methano-2,4,3-penzonooxadiepine 3-oxide...1-naphthyl methylcarbamate , methylcarbamic acid m-tolyl.

Methylcarbamic acid o-(sec-butylphenyl)
Pyrethroid insecticides such as (hereinafter abbreviated as BPMC)...pyrethrin, allethrin,
Antibiotics such as resmethrin and etofenbrox
...Other insecticides such as plasticidin S, kasugamycin, polyoxin, oxytetracycline, validamycin A...cartap hydrochloride, S-methyl N-(methylcarbamoyloxy)thioacetimidate. Examples include bensultap and thiocyclam. However, the present invention is not limited to these examples. In the present invention, one or more of the above-mentioned agricultural chemical active substances may be used in combination. For 100 parts by weight of the drug, the content of Compound M is 0,0001 to 5 in powder form.
Approximately 0 parts by weight is suitable for wettable powders and sol formulations, approximately IO to 90 parts by weight, and Q, approximately 1 to 50 parts by weight for granules. In powder agents, it is more effective to contain it preferably in an amount of 0.001 to 20 parts by weight.

The other active ingredients are appropriately used in a weight ratio of 10:1 to 1:10 with respect to Compound M, but preferably 7:1 to 1:10.
; 1 to 1 near is appropriate.

Furthermore, in the agricultural chemical composition of the present invention, in addition to Moeki's oxide or hydroxide of zinc, calcium, or magnesium, by adding a specific amine, compound M
It has also been found that the isomerization of isomerization can be more effectively suppressed.

As the amine compound used in the present invention, primary amines, secondary amines, and tertiary amines having 4 or more carbon atoms are widely used. Particularly preferred are aliphatic amine compounds or diamine compounds. In particular, amine compounds having the formula [wherein x, y, and z each represent a hydrogen atom or an alkyl group, provided that at least one of X, Y, and Z represents an alkyl group], the alkyl The group may have an ether bond with oxygen interposed therebetween, or may be substituted with a hydroxyl group and/or an amino group. ] An amine compound having a carbon r/i of 4 to 100 is preferable. As these aliphatic substituents, particularly preferred are polyoxyethylene groups, polyoxinepropylene groups, and/or alkyl groups which may have amino groups or hydroxyl groups as substituents. Furthermore, as the diamine compound, alkylene diamines such as ethylene diamine and trimethylene diamine are preferable, and even if these diamines are substituted with a polyoxyethylene group, a polyoxypropylene group, and/or an amino group or a hydroxyl group. Good alkyl groups are preferred.

The polyoxyethylene and polyoxypropylene groups are preferably groups in which one or more oxyethylenes or oxypropylenes are linked, and each terminal is a hydrogen atom.

Examples of the amine compound having 4 or more carbon atoms used in the present invention include amines represented by the following formula.

[In the formula, R represents an alkyl group (preferably having 4 to 2 o carbon atoms), Z'l:t-(CI, -CI-110)m[1 or CI.

n represents a positive integer (preferably, m is an integer of 1 to 4o, n is an integer of 2 or 3), and each R, Z', m, and n may be the same or different. . The total number of carbon atoms in each amine is 4 or more. ] In the case of an agrochemical composition containing an acidic substance in addition to compound M, among the amine compounds represented by the above formula, the amine compound represented by the following formula can be used without adversely affecting other components. It has the effect of suppressing the isomerization of.

[Each symbol in the formula is as defined above]

Furthermore, among these amine compounds, the following formulas (+) to (5)
The amine compound represented by has a low adverse effect on other components, an isomerization prevention effect of compound M, a stabilizing effect on the formulation,
It was confirmed that it is particularly suitable in terms of low toxicity to crops and humans and livestock.

R, NII, (+) [
In formulas (1) to (5), R4, Rs, and Re are alkyl groups having 4 to 20 carbon atoms, and Z is -CI(,CH,0-
or -CHCHtO, n is 2 or 3゜ H3 a-1 represents an integer of 1 or more, and 4≦a+b+c+d
≦40.3≦e+f+g≦40.3≦h+i+j≦40
．． 2≦ and +1≦40] A mixture of Compound M, which has an excellent effect on controlling rice blast, sesame leaf blight, etc., and Cartap hydrochloride, which has an excellent effect on various insect pests, such as gnatworm and planthopper. Among the above-mentioned amines, the amine represented by formula (5), which has no adverse effect on cartap hydrochloride and is excellent in the isomerism-preventing effect of compound M, is particularly desirable. Examples of the amines represented by formula (5) include polyethylene ethylene (hereinafter sometimes abbreviated as POE) (2-40) laurylamine, POE (2-40), and POE (2-40).
0) Stearylamine, POE (2-40) Oleylamine, polyquine propylene (hereinafter sometimes abbreviated as POP) (2-40) Laurylamine, POP (2-40)
40) Stearylamine, POP(2-40)oleylamine, etc. are particularly preferred.

The amine compound used in the present invention includes various reagents [for example, the amine of (1)], surfactants [for example, the formulas (2) to (4)
), or those commercially available as pigment dispersants and corrosion inhibitors (for example, the amine of formula (5)) may be used, or triethanolamine or ethylenediamine with ethylene oxide or propylene oxide added thereto may be used. (For example, Fuji Horiguchi, Synthetic Surfactants 3) (see publication)
Or general amine synthesis methods (for example, Nippon Chemistry complete series:
Experimental Chemistry Course, 20. Synthesis of organic compounds (see Maruzen)
It can also be produced according to conventional methods. Commercially available amines that can be used in the present invention include, for example, laurylamine, jetanolamine, triethanolamine, ethylenediamine, dimethylaminopropane, and dimethylaminobrobylamine.

The addition m of the amine is not particularly limited, but approximately 0 m is added to the formulation.
．． It is effective to use 0.05 to 10 parts by weight, preferably about 0.1 to 5 parts by weight.

The agrochemical composition of the present invention is produced by formulating the above-mentioned components into various agrochemical formulations by means known per se. For example, Compound M is mixed with other agrochemical active ingredients if necessary, metal oxides or hydroxides, other adjuvants, carriers, and if necessary the above-mentioned specific amines, etc. using, for example, a Nauta mixer. To obtain powders and wettable powders, it is further ground in a grinder. In addition, the method for producing granules may be, for example, a wet granulation method that involves mixing in a Nauta mixer, then adding water, kneading, granulating, and drying, but is not limited to this method. It can also be obtained by coating the core grains with pesticide active ingredients and other adjuvants. As a method for producing a sol, Compound M and, if necessary, other pesticide active ingredients and metal oxides or hydroxides,
It can be obtained by mixing other adjuvants and the above amine with a liquid (water or oil) and wet-pulverizing the mixture. However, the invention is not limited to these examples.

The amount used when applying the agrochemical composition of the present invention varies depending on the application situation, application time, application method, target pests, cultivated crops, etc., but in general, the amount used as the active ingredient (Compound M and other mixed active ingredients) Paddy field.

The amount is about 0.05 to 50 g, preferably about 0.1 to 15 g per area of lawn or field.

Effects of the Invention According to the present invention, even when stored for a long period of time, the compound M in the preparation
The isomerization reaction from E-form to E-form is suppressed, and therefore a stable agrochemical formulation can be provided.

EXAMPLES Hereinafter, the present invention will be explained in further detail by describing Examples, Reference Examples, and Test Examples. Note that all percentages and parts used herein indicate weight percentages and parts by weight unless otherwise specified.

In the following examples, the above-mentioned compound M and Obi M were used as compound M. These are four bodies, so to distinguish them from the corresponding E bodies, they are denoted as M, (Z), and Mt(z), and the corresponding E bodies are labeled M, respectively.

(E) and Mt(E).

Example! Compound M, (Z) 2 parts by weight, fusaride 1.5 parts by weight,
2 parts by weight of cartap hydrochloride, 3 parts by weight of BPMC, 0.3 parts by weight of isopropyl acid phosphate, 5 parts by weight of white carbon, 0.2 parts by weight of zinc oxide, 86 parts by weight of zinc
Weigh out parts by weight and mix in a sieve machine. Mix again with a flash mixer to make a powder.

Example 2 Compound M, (Z) 2 parts by weight,
5 parts by weight, BPM03 parts by weight, white carbon 5 parts by weight.

0.5 parts by weight of isopropyl acid phosphate, IO parts by weight of zinc oxide, and 78 parts by weight of clay are weighed out and prepared as a powder in the same manner as in Example I.

Example 3 Compound M, (Z) 2 parts by weight, fusaride 1.5 parts by weight,
2 parts by weight of cartap hydrochloride, 0.3 parts by weight of isopropyl acid phosphate, 2 parts by weight of white carbon,
Weigh out 0.1 part by weight of zinc oxide and 1 part by weight of clay, and prepare a powder in the same manner as in Example 1.

Example 4 Compound M, (Z) 2 parts by weight, fusaride 1.5 parts by weight,
3 parts by weight of I3PM0, 0.5 parts by weight of isopropyl acid phosphate, 5 parts by weight of white carbon, 78 parts by weight of calcium oxide IO, and 78 parts by weight of clay are prepared in the same manner as in Example I to prepare a powder.

Example 5 Compound M, 2 fflfffi parts of (Z), 2 parts of cartap hydrochloride, 0.3 parts of isopropylambutophosphate
Parts by weight, 0.2 parts by weight of zinc oxide, 2 parts by weight of white carbon, and 93.5 parts by weight of clay were weighed and prepared in the same manner as in Example I to prepare a powder.

Example 6 Compound M, (Z) 2 parts by weight, fusaride 1.5 parts by weight,
3 parts by weight of I3PMC, 0.3 parts by weight of isopropyl acid phosphate, 5 parts by weight of white carbon, 0.5 parts by weight of magnesium oxide, and 87.7 parts by weight of clay were weighed and prepared in the same manner as in Example 1 to form a powder.

Example 7 Compound M, (Z) 2 parts by weight, fusaride 1.5 parts by weight,
Example 1: 2 parts by weight of bensultap, 0.3 parts by weight of validamycin A, 0.3 parts by weight of isobrovir and phosphate, 3 parts by weight of white carbon, 5 parts by weight of zinc oxide, and 85.9 parts by weight of clay. Make a powder in the same manner as above.

Example 8 Compound M, (Z) double reaction, fusaride! , 5 parts by weight,
Bensurtap 2 parts by weight, BPMC 3 parts by weight.

Isobrovir antudophosphate 0.5Tffff
1 part by weight, 5 parts by weight of poite carbon, 10 parts by weight of zinc oxide, and 76 parts by weight of clay, Example! Make a powder in the same manner as above.

Example 9 Compound M, (Z) 2 parts by weight, fusaride 1.5 parts by weight,
Weigh 2 parts by weight of Henstletap, 0.2 parts by weight of isopropyl acid phosphate, 1 part by weight of white carbon, 5.0 parts by weight of magnesium oxide, and 88.3 parts by weight of clay, and prepare a powder in the same manner as in Example 1. .

Example 10 Compound M, (Z) 2 parts by weight, fusaride 1.5 parts by weight,
Etofenbrox 0.5 parts by weight, Validamycin A
013 Shigesatobe, Irganox 10100.05 parts by weight, potassium sorbate 0.1 parts by weight.

Isopropyl acid phosphate 0.2ffiff
i part, 2 parts by weight of white carbon, 2 parts by weight of zinc oxide.

A powder was obtained in the same manner as in Example 1 by weighing 91.35 parts by weight of clay.

Control formulation example 1 Compound M, (Z) 2 parts by weight, fusaride 1.5 parts by weight,
2 parts by weight of cartap hydrochloride, 3 parts by weight of BPMC.

Five parts by weight of white carbon, 0.3 parts by weight of isopropyl acid phosphate, and 86.3 parts by weight of clay were weighed and the same procedure as in Example 1 was carried out to obtain a powder.

Control formulation example 2 Compound M, (Z) 2 parts by weight, fusaride 1.5 parts by weight,
3 parts by weight of BPMC, 5 parts by weight of white carbon.

A powder was obtained in the same manner as in Example 1 by weighing 0.5 parts by weight of isopropyl acid phosphate and 88 parts by weight of clay.

Control formulation example 3 Compound M! (Z) 2 parts by weight, 0.3 parts by weight of isopropyl acid phosphate, 1 part by weight of white carbon,
Weigh 96.7 parts by weight of clay and use the same formula (η) as in Example 1 to obtain a powder.

Control formulation example 4 Compound M I (Z) 2 parts by weight, fusaride 1.5 parts by weight, cartap hydrochloride 2 parts by weight, isopropyl acid phosphate 0.3 parts by weight, white carbon 2 parts by weight, clay 92.2 parts by weight was weighed and made into a powder in the same manner as in Example I.

Control formulation example 5 Compound M 2 (z) 2 parts by weight, cartap hydrochloride 2 parts by weight, isopropyl acid phosphate 0.3
Parts by weight, 2 parts by weight of white carbon, and 93.7 parts by weight of clay were weighed and prepared in the same manner as in Example 1 to prepare a powder.

Control formulation example 6 Compound M2 (Z) 2 parts by weight, fusaride 1.5 parts by weight,
3 parts by weight of BPMC, 0.3 parts by weight of isopropyl acid phosphate, 5 parts by weight of white carbon, 8 parts by weight of clay
8.2 parts by weight was weighed out and the same procedure as in Example 1 was carried out to obtain a powder.

Control formulation example 7 Compound M, (Z) double (1 part, fusaride 1.5 parts by weight, bensultap double parts, validamycin A 0.3 parts by weight, potassium sorbate 0.1 part by weight, isopropyl acid phosphate 0. 3 parts by weight.

3 parts by weight of white carbon and 90.8 parts by weight of clay were weighed and prepared in the same manner as in Example 1 to form a powder.

Control Formulation Example 8 Compound M, (Z) 2 parts by weight, Fusaride 15 parts by weight, Bensultap 2 parts by weight, 13PMC 3 parts by weight.

Weighed 0.5 parts by weight of isopropyl acid phosphate, 5 parts by weight of white carbon, and 86 parts by weight of clay,
A powder was prepared in the same manner as in Example 1.

Control formulation example 9 Compound M2 (Z) 2 parts by weight, fusaride 1.5 parts by weight, 1 part,
2 parts by weight of bensultap, 0.2 parts by weight of isopropyl acid laosphate, 1.0 parts by weight of white carbon, and 93.3 parts by weight of clay were weighed out, and a powder was prepared in the same manner as in Example 1.

Control formulation example 10 Compound M, '(Z) 2 parts by weight, fusaride 1.5 parts by weight, etofenbrox 0.5 parts by weight, validamycin A 0.3 parts by weight, potassium sorbate 0.1 parts by weight,
Irganox 1010 0.05 weight ff1L 0.2 parts by weight of isopropyl acid phosphate, 2 parts by weight of white carbon, and 93.35 parts by weight of clay were weighed, and a powder was obtained in the same manner as in Example 1.

Test Example 20 g of each of Examples 1 to 10 and Control Formulation Example 1 to 10 was placed in a sample bottle, sealed tightly, and stored at room temperature for one year. Immediately after the expiration of the period, a sample was taken out and the content of the 9-isomer and Z-isomer of compounds M, , M, was measured by high performance liquid chromatography.

The content ratio of compound M(E) after one year of storage at room temperature was calculated using the following formula.

Content rate (%) of compound M (E) = ResultsContinuedFrom the above results, the formulation to which the oxide or hydroxide of a specific metal of the present invention was added was superior to the control formulation to which no such metal was added. It can be seen that it has an effect of suppressing isomerization to .

Agent Patent Attorney Iwa 1) Hiroshi

Claims (2)

[Claims] (1) Pyrimidine represented by the formula ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (Z form) [In the formula, Ar is a phenyl group substituted with a lower alkyl group, and R_1, R_2 and R_3 are lower alkyl groups] Derivatives or salts thereof and (2) A stabilized agricultural chemical composition characterized by containing an oxide or hydroxide of zinc, calcium or magnesium.