JPH01207206A - Agricultural chemical composition - Google Patents

Abstract

PURPOSE:To obtain the above composition having improved stability, storable without causing isomerization reaction of the active component, free from toxicity to crops, human and animals and effective against rice blast, Helminthosporium leaf spot, etc., by using a pyrimidine derivative or its salt in combination with a specific amine compound 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) a >=4C amine compound. The above amine compound is especially preferably a compound of formula II (R6 is 4-20C alkyl; Z is -CH2CH2O-, etc.; 2<=K+1<=40) such as polyoxyethylene (2-40 degree of polymerization) laurylamine. 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 I is preferably about 0.0001-50 pts.wt., for dust formulation and about 10-90 pts.wt. for wettable powder 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 [I], which has excellent control and treatment effects on rice blast, sesame leaf blight, and the like.

A pyrimidine derivative (hereinafter abbreviated as compound M) represented by the conventional technical formula [in the formula, 8r is a phenyl group substituted with a lower alkyl group, and R, R2 and R5 are lower alkyl groups]
is a compound useful as a fungicide for agriculture and horticulture, and is effective in controlling diseases and fungi such as rice blast, sesame leaf blight, and micrococcal core disease, which are described in JP-A-55-151570.

However, when Compound M is formulated into a formulation, there is a problem in that it undergoes an isomerization reaction under the influence of other ingredients.

That is, compound M relates to a double bond between C-N.

However, its geometric isomers of the formula R+ exist, 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 is in two forms, is formulated into a formulation, its E form may increase due to the influence of other coexisting components. However, the E-form is less preferable than the 2-form because of the 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. ''There is a strong 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 acidic regions. . In addition, there are acidic substances among the auxiliary ingredients commonly used in formulation, and when compound M is mixed with these, compound M undergoes isomerization. Furthermore, some carriers also promote isomerization to the E form.

Therefore, an object of the present invention is to prevent Compound M from becoming gastric 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. , Unexpectedly, when a specific amine compound is added to such a preparation, compound M
The present inventors have found that the isomerization reaction of isomerization is suppressed, and that there are no toxicity problems for crops, humans or livestock, and after further studies, they have completed the present invention.

That is, the present invention provides a pyrimidine derivative or a salt thereof represented by the formula [wherein A is a phenyl group substituted with a lower alkyl group, R, R, and R1 are lower alkyl groups] and a carbon number The present invention relates to a stabilized agricultural chemical composition characterized by containing an amine compound having 4 or more.

The agricultural chemical active ingredient compound M of the present invention is
-151570.

As the salt of the pyrimidine compound represented by formula (1),
Examples include hydrochloric acid, phosphoric acid, sulfuric acid, benzenesulfonic acid, methanesulfonic acid, p-toluenesulfonic acid, trichloroacetic acid, ogizalic acid, and the like.

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

As the amine compound used in the present invention, a wide range of primary amines, secondary amines, and tertiary amines having 4 or more carbon atoms are used. Particularly preferred are aliphatic amine compounds or diamine compounds. In particular, as an amine compound, the alkyl group has the formula [wherein, , an ether bond may be present with oxygen interposed therebetween, and the ether bond may be substituted with a hydroxyl group and/or an amino group. ] An amine compound having 4 to 100 carbon atoms is preferable. As these aliphatic substituents, particularly preferred are polyoxyethylene groups, polyoxypropylene groups, and/or alkyl groups which may have amino groups or hydroxyl groups as substituents. Further, as the diamine compound, alkylene diamines such as ethylene diamine and trimethylene diamine are preferable, and as substitutes for these diamines, polyoxyethylene groups, polyoxypropylene groups, and/or amino groups or hydroxyl groups are substituted. An optional alkyl group is preferred.

Preferably, the polyoxyethylene and polyoxypropylene groups each have one or more oxyethylenes or groups in which one or more oxyethylenes 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 J-formula.

[In the formula, R is an alkyl group (preferably having 4 to 20 carbon atoms), and Z' is a group represented by -(CHtCl1to)m+-1 or =(C1l-CI-1,0)mIf, m .

ll3 n represents a positive integer (preferably, m is an integer of 1 to 40, n is an integer of 2 or 3), and each 11. 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 corresponds to the surface length]

Furthermore, among these amine compounds, the following formulas (1) 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 also confirmed that it is particularly suitable in terms of low toxicity to crops and humans and livestock.

R=NHt (1) [In formulas (1) to (5), +1. , rt5. R, is an alkyl group having 4 to 20 carbon atoms, Z is -Cr, t tc II
, O- or -Ctr-C1120-+ n is 2 or 3° H3 a-1 represents an integer of 1 or more, and 4≦a+b+c+d
≦40.3≦e−B+g≦40.3≦11+i+j≦4
0.2≦ and +1≦40] 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 the Japanese grasshopper 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 polyoxyethylene (hereinafter sometimes abbreviated as 'OE) (2-40) laurylamine, POE (2-40), and POE (2-40).
40) Stearylamine, r'0E (2-40) oleylamine, polyoxypropylene (hereinafter sometimes abbreviated as POP) (2-40) laurylamine, POP (
Particularly preferred are 2-40) stearylamine, POP(2-40) oleylamine, and the like.

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 commercially available pigment dispersants and corrosion inhibitors (for example, the amine of formula (5)), or triethanolamine or ethylenediamine to which ethylene oxide or propylene oxide is added. (For example, see Fu Horiguchi: Synthetic Surfactants Sankyo Publishing) or a general synthesis method for amines (For example, see Chemical Society of Japan G = Experimental Chemistry Course, 20. Synthesis of Organic Compounds ■ Marukubi) 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, and dimethylaminopropane. Examples include dimethylaminopropylamine.

The amount of the amine added is not particularly limited, but approximately 0
．． It is effective to use from 0.05 to IO parts by weight, preferably from about 0.1 to 5 parts by weight. Usually, the composition of the present invention is prepared by blending the pyrimidine derivative represented by the general formula (I) or its salt, that is, the compound M and the above-mentioned amine, with other agrochemical active substances and various carriers and auxiliary ingredients as appropriate to form a powder.
1 tablet of hydrating powder.

It is in the form of a sol, etc. Here, various surfactants (eg, lignin sulfonate, alkylbenzene sulfonate) are used as carriers or auxiliary components.

Polyquine ethylene alkyl ether, alkylnaphthalene sulfonate, etc.), dispersant (e.g. ethylene glycol, glycerin, etc.), flow aid (e.g. white carbon, etc.), fixing agent, youth absorbent.

Antioxidants (e.g. dibdelhydroxytoluene, 4
．． 4-thiobis-6-tart-butyl-3-methylphenol, pentaerythrotyltetrakis [3-(3
, 5-di-t-butyl-4-hydroxyphenyl)
1 Bionate] (manufactured by Ziba Geigy, hereinafter referred to as Irganox-+010), etc.).

preservatives (e.g. sorbic acid, potassium sorbate, etc.),
Examples include synergists, wetting agents, stabilizers, solvents, excipients, diluents, suspension agents, spreading agents, penetrating agents, mucilage agents, and the like.

Pesticide active substances other than Compound M include sulfur-based, organophosphorus-based, a-arsenic-based, and organochlorine-based fungicides, (T
Examples include insecticides and acaricides such as phosphorus, organochlorine, carbamate, and pyrethroid, as well as various antibiotics. More specifically, carriers and auxiliary ingredients include vegetable powders such as soybean flour, tobacco flour, wheat flour, and wood flour, clays (kaolin, bentonite,
acid clay, etc.).

In addition to mineral powders such as talc (talc, waxite powder, etc.), silicas (diatomaceous earth, mica powder, etc.), solid carriers and hli support components such as calcium carbonate, sulfur powder, and activated carbon are used. Ru. Some examples of the above pesticide active substances include organic sulfur fungicides: ethylene bis(dithiocarbamic acid) zinc, ethylene bis(dithiocarbamic acid) manganese, ethylene bis(dithiocarbamic acid) ammonium, bis(dimethyldithiocarbamic acid) ethylene bis. (
Organophosphorus fungicides such as dizinc dithiocarbamate...
・S-benzyl 0.0-diisopropyl thiophosphate,
Arsenic-based fungicides such as didiophosphate S, s-diphenyl 0-ethyl, organic base-based fungicides such as iron methanarsonate, iron ammonium methanarsonate, etc., and pentachlorophenol.

Other fungicides such as tetrachloroisophthalonitrile, 4,5,6.7-titrachlorophthalide...trinkrazole (hereinafter abbreviated as TC), N-()lichloromethylthio)-4-cyclohexene- 1,2-dicarboximide, phenazine 5
Organophosphorus insecticides such as -oxide, l-(butylcarbamoyl)-2-benzimidazole methylcarbamate...MEP, dithiophosphoric acid S-[
1,2-bis(ethoxycarbonyl)edyl]0.0-
Dimethyl, 2,2-dichlorovinyl phosphate dimethyl, 2,2,2-trichloro-1-hydroxyedylphosphonic acid dimethyl, N-acetylposporamide thiolate 01S-dimethyl.

Dimethyl phosphate (E)-1-methyl-2-methylcarbamoylvinyl, dithiophosphate 0.0-dimethyl
Organochlorine insecticides such as S-[α-(ethoxycarbonyl)benzyl], dithiophosphate 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-benzodioxathiepine 3-oxide...l-naphdyl methylcarbamate , methylcarbamic acid m-tolyl.

Methylcarbamic acid 0-(scc-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, etc. Cartap hydrochloride, S-methyl N-(methylcarbamoyloxy)thioacetimidate, bensultap, etc. 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. With respect to 100 parts by weight of the drug, the content of compound M is approximately 0,000 to 50 parts by weight in powder formulations, 10 to 90 parts by weight in wettable powders and sol formulations, and 0.1 to 50 parts by weight in granules. The degree is appropriate. For powders, more preferably 0.0
It is effective to contain it in an amount of 0.01 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.
:l-1 near is suitable.

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 and, if necessary, other agrochemical active ingredients, amines, and other adjuvants.

The carrier is mixed, for example in a Nauta mixer. To obtain powders and wettable powders, it is further ground in a grinder. In addition, as a method for manufacturing granules, for example, after mixing with a Nauta mixer, adding water,
It can be obtained by a wet granulation method that involves kneading, granulation, and drying steps, but is not limited to this method.Agrochemical active ingredients and other adjuvants can be added to core particles of river sand, pumice, or vermiculite. It can be obtained by a coating method.

As a method for producing a sol, Compound M and, if necessary, other agrochemical active ingredients, amines, other auxiliaries, and liquids (water,
Alternatively, it can be obtained by mixing and wet grinding (or oil). 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, one of 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 % and parts used herein refer to i[Jt% and parts by weight unless otherwise specified.

In the following examples, the above compounds M and M were used as compound M. Since these are two bodies, in order to distinguish them from the corresponding E bodies, they are denoted as Ml (Z) and M, (Z), respectively, and the corresponding E bodies are denoted as M, (E) and M2 (E), respectively.
) is displayed.

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 nPM0.

0.5 parts by weight of isopropyl acid phosphate, 5 parts by weight of white carbon, n-amylamine! weight part,
85 parts by weight of clay was weighed and mixed in a Raikai machine. Further, mix again with a flash mixer to obtain a powder.

Example 2 Compound M, 2 parts by weight of (Z), 1 part by weight of trifuclazole, 2 parts by weight of cartap hydrochloride, 3 parts by weight of 13PM0, 0.5 part by weight of isopropyl acid phosphate, 1 part by weight of white carbon 5 parts, laurylamine 1 part by weight and 85.5 parts by weight of clay were weighed and the same procedure as in Example 1 was carried out to obtain a powder.

Example 3 Compound M, (Z) 2 parts by weight 1 fusalide 1.5 parts by weight,
Weighed 2 parts by weight of cartap hydrochloride, 0.5 parts by weight of isopropyl acid phosphate, 1 part by weight of polyoxyethylene (5) triethanolamine, 2 parts by weight of white carbon, and 91 parts by weight of clay, and prepared in the same manner as in Example 1. Get the powder.

Example 4 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 validamycin A, 0.3 parts by weight of isopropyl acid phosphate
parts, 2 parts by weight of white carbon, polyoxyethylene (
5) 1 part of ethylenediamine.

90.9 parts by weight of clay was weighed and the same procedure as in Example 1 was carried out to obtain a powder.

Example 5 Compound M, (Z) 2 parts by weight, Buza 9111.5 parts by weight,
2 parts by weight of cartap hydrochloride, 3 parts by weight of BPMC.

0.5 mm part of isopropyl acid phosphate, 5 parts by weight of white carbon, 1 part by weight of polyoxyethylene (3) coconut alkylaminopropylamine, clay 85
Parts by weight were weighed and the same procedure as in Example I was carried out to obtain a powder.

Example 6 Compound M, (Z) 2 parts by weight, fusaride 1.5 parts by weight,
3 parts by weight of I3PMC, 0.5 parts by weight of isopropyl acid phosphate, 5 parts by weight of white carbon, 1 part by weight of polyoxyethylene (2) laurylamine, 8 parts by weight of clay
8 parts by weight were weighed out and the same procedure as in Example I was carried out to obtain a powder.

Example 7 Compound M, (Z) 2 parts by weight, Fusa 9111.5 parts by weight,
Weigh out 3 parts by weight of I3PM0, 0.5 parts by weight of isopropyl acid phosphate, 5 parts by weight of white carbon, 1 part by weight of polyoxyethylene (15) laurylamine, and 88 parts by weight of clay, and obtain a powder in the same manner as in Example 1.

Example 8 Compound M, (Z) double; 3+ thing, y”J-rai F I
, 5 parts by weight, 2 parts by weight of cartap hydrochloride, 93 parts by weight of validamycin AO, 0.3 parts by weight of isopropyl acid phosphate, 2 parts by weight of white carbon, 1 part by weight of polyoxyethylene (2) stearylamine.

90.9 parts by weight of clay was weighed and the same procedure as in Example 1 was carried out to obtain a powder.

Example 9 Compound M, (Z) 2 parts by weight, Buza 9111.5 parts by weight,
2 parts by weight of cartap hydrochloride, 0.5 parts by weight of isopropyl acid phosphate, 2 parts by weight of white carbon,
A powder was obtained in the same manner as in Example 1 by weighing 1 part by weight of polyoxyethylene (40) stearylamine and 91 parts by weight of clay.

Example 10 Compound M, 2 parts by weight of (Z), 1.5 parts by weight of Buzalide,
Cartap hydrochloride 2 parts by weight, isopropyl acid phosphate 0.5 parts by weight, white carphone 2 parts by weight,
Polypropylene (2) 1 part by weight of laurylamine and 91 parts by weight of clay were weighed out and the same procedure as in Example I was carried out to obtain a powder.

Example 11 Compound Ml(E) 0.6 parts by weight, compound Ml(Z) 1.
Quadruple part, isopropyl acid phosphate 0.2
Parts by weight, 1 part by weight of white carbon, 1 part by weight of polyoxyethylene (2) laurylamine, and 95.8 parts by weight of clay were weighed, and the same procedure as in Example 1 was carried out to obtain a powder.

Example 12 Compound M, (Z) 2 parts by weight, cartap hydrochloride 2 parts by weight, isopropyl acid phosphate 0.5 parts by weight,
A powder was obtained in the same manner as in Example 1 by weighing 1 part by weight of polyoxyethylene (5) triethanolamine, 2 parts by weight of white carbon, and 94.5 parts by weight of clay.

Example 13 Compound M, (Z) 2 parts by weight, fusaride 1.5 parts by weight,
2 parts of cartap hydrochloride, 3 parts of I3PMC.

0.5 parts by weight of isopropyl acid phosphate, 5 parts by weight of poite carbon, parts by weight of stearylamine I,
Example by weighing 85 parts by weight of clay! Obtain a powder in the same manner as above.

Example 14 Compound M, (Z) 2 parts by weight, fusaride 1.5 parts by weight,
12 parts by weight of bensultara, 0.3 parts by weight of validamycin A, 0.3 parts by weight of isopropyl acid phosphate, 3 parts by weight of white carbon, 1 part by weight of polypropylene (2) laurylamine, and 89.9 parts by weight of clay were weighed, and Example A powder is obtained in the same manner as in I.

Example 15 Compound M, (Z) 2 parts by weight, fusaride 1.5 parts by weight, bensultap 2 parts by weight, isopropyl acid phosphate 0.2 parts by weight, white carbon 1 part by weight, polyoxyethylene (5) ethylenediamine 1 part by weight 92.3 parts by weight of clay were weighed, and the same procedure as in Example 1 was carried out to obtain a powder.

Example 16 Compound M, (Z) 2 parts by weight, fusaride 1.5 parts by weight,
Validamycin A 013 parts by weight, etofenbrox 0.5 parts by weight, isopropyl acid phosphate 0.3 parts by weight, White Bu J-bon 2.0 parts by weight, Irganox 1010 0.05 parts by weight.

1 part by weight of polyoxyethylene (2) laurylamine.

92.35 parts by weight of clay was weighed out and a powder was obtained in the same manner as in Example 1.

Control formulation example 1 Compound M, (Z) 2 parts by weight, fusaride 1.5 parts by weight,
2 parts by weight of cartap hydrochloride, 33 parts by weight of I3PMC.

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

Control formulation example 2 Compound M, (E) 0.6 parts by weight, compound Ml(Z) 1.
4 municipal bond section, isopropyl acid phosphate 0.2
Part by weight, 1 part by weight of white carbon, and 96.8 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 3 Compound Mt(m) 0.4 parts by weight, Compound M2(Z)+,
6-fold ffi part, isobrovir antudophosphate 0
．． 5 parts by weight, 1 part by weight of white carbon, 96% clay.
5 parts by weight were weighed out and the same procedure as in Example 1 was carried out to obtain a powder.

Control formulation example 4 Compound M, 2 parts by weight of (Z), 1 part by weight of trifuclazole, 2 parts by weight of cartap hydrochloride, 3 parts by weight of BPM0, 0.5 parts by weight of isopropyl acid phosphate, 5 parts by weight of white carbon, Clay 86 A powder agent was obtained in the same manner as in Example 1 by weighing .5 parts by weight.

Control formulation example 5 Compound M, (Z) 2 parts by weight, fusaride 1.5 parts by weight,
2 parts by weight of cartap hydrochloride, 0.5 parts by weight of isopropylambutophosphate, 2 parts by weight of white carbon,
92 parts by weight of clay was weighed out and a powder was obtained in the same manner as in Example 1.

Control formulation example 6 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 Varigmine Δ, 0.3 parts by weight of isopropyl acid phosphate; 11'<, 2 parts by weight of white carbon, Clay-9
A powder was obtained in the same manner as in Example 1 using a 1.5-layer weighing unit.

Control formulation example 7 Compound M, (Z) 2 parts by weight, fusaride 1.5 parts by weight,
Three parts of I3PMC, 0.5 parts by weight of isopropyl acid phosphate, 5 parts of white carbon IM≦, and 88 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 8 Compound M, (Z) 2 parts by weight, cartap hydrochloride 2 parts by weight, isopropyl acid phosphate 0.5 parts by weight,
2 parts by weight of white carbon, 5 parts by weight of clay 93°
'ffi example! Obtain a powder in the same manner as above.

Control formulation example 9 Compound M, 2 parts of (Z), 1.5 parts by weight of fusaride,
Weigh 2 parts by weight of Henstletap, 13 parts by weight of validamycin AO, 0.3 parts by weight of isobrovir and phosphate, 3 parts by weight of white carbon, and 90.9 parts by weight of clay, and obtain a powder in the same manner as in Example 1. .

Control formulation example IO Compound M, (Z) 2 parts by weight, fusaride 1.5 parts by weight,
2 parts by weight of bensultap, 0.2 parts by weight of isopropyl acid phosphate, 1 part by weight of white carbon, and 93.3 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 11 Compound M, (Z) 2 parts by weight, fusaride 1.5 parts by weight,
Validamycin A 0.3 parts by weight, etofenbrox 0.5 parts by weight, isopropyl acid phosphate 0.3 parts by weight, white carbon 2.0 parts by weight, Irganox 1010 0.05 parts by weight.

93.35 parts by weight of clay was weighed and crushed in the same manner as in Example I to obtain a powder.

Test example example! -16 and Control Formulation Examples 1 to 11 (20 g each) were placed in sample bottles, sealed tightly, and stored at room temperature for I year. Immediately after the period has elapsed, a sample is taken out and subjected to high performance liquid chromatography to identify Compound M8. The contents of E-form and Z-form of Mt were measured.

Content rate (%) of compound M (E) = The rate of change of compound M(E) was determined using the following formula.

Rate of change in compound M(E) - Content rate of compound M(E) after one year - Cf content rate of compound M(E) at the start of the test Examples 1 to 10.12 to 16.
In control formulation examples 1, 4 to 11, compound M (E
) content is 0%, Example 11. Same content a of control formulation example 2
The RF content rate is 30%, and the RF content rate of Control Formulation Example 3 is 20%.

(See the margin below) ResultsContinued from the above results, it can be seen that the formulation to which the specific amine of the present invention is added exhibits a superior effect of inhibiting isomerization to isomerization to the E form, compared to the control formulation to which no such amine is added.

Agent Patent Attorney Iwa 1) Hiroshi

Claims (1)

[Claims] 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 represent a lower alkyl group] The represented pyrimidine derivative or its salt and carbon number 4
A stabilized agricultural chemical composition characterized by containing an amine compound having the above.