JPH0193575A - Pyrimidine derivative and agricultural and horticultural fungicide containing said derivative as active component - Google Patents

Abstract

NEW MATERIAL:The pyrimidine derivative of formula I {X is Cl or F; R<1> is 1-4C alkyl; R<2> is CH3 or group of formula II; R<3> and R<4> are H, 1-6C branched or cyclic alkyl, [COOR<5>(R<5> is H or lower alkyl)-substituted] alkyl, lower alkenyl or group of formula III (R<6> is H, halogen, etc.); when X is Cl, R<6> is not CH3 or alkenyl}. EXAMPLE:4-(n-Butylamino)-5-fluoro-6-methyl-2-methylthiopyrimidine. USE:An active component for agricultural and horticultural fungicide. It exhibits high controlling effect against gray mold of kidney beans, powdery mildew of cucumber, etc., by foliar treatment and is effective even to resistant fungi. It does not cause adverse effects such as phytotoxicity to crops and is useful for the treatment of paddy rice, plowed field, orchard, etc. PREPARATION:A compound of formula I wherein R<2> is CH3 can be produced by reacting a compound of formula IV (R<2> is CH3) with amines of formula V in an organic solvent in the presence of a basic substance.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a novel pyrimidine derivative, which can be used as an agricultural and horticultural fungicide in paddy fields, fields, orchards, etc.

[Conventional technology]

Botrytis and powdery mildew are important diseases in the cultivation of vegetables and fruit trees, so lobral, benomyl, thiophanate methyl, etc. have been frequently used. As a result, the problem of drug-resistant bacteria has emerged, and the drug's efficacy is no longer sufficient. Therefore, research and development of new drugs is actively conducted.For example, in West German Patent No. 3436380, 2-
There is a description that arylamino-5-chloro-6-methy, -4-methylthiopyrimidine and 4-allylamino-5-chloro-6-methyl-2-methylthiopyrimidine are effective against gray mold, and JP-A No. 62-99305 The number is 2
There is also a description that -anilino-4-chloro-6-substituted pyrimidine exhibits a bactericidal effect.

[Problem that the invention seeks to solve]

The emergence of drug-resistant bacteria to conventional fungicides has become a very serious problem, and the control effect has decreased, and in some areas, no control effect has been observed at all. Therefore, the present inventor synthesized a new pyrimidine derivative shown in (1) below using a new mother core, and utilized this as a fungicide as an active ingredient, thereby overcoming the drawbacks of conventional fungicides. The aim is to provide a useful agricultural and horticultural fungicide that is highly effective against bacteria that are resistant to existing pesticides, and that does not cause harmful effects such as phytotoxicity on plants.

(In the formula, X, R', R2, R3, and R' represent the following.) The compound of formula (1) of the present invention can be produced by the following method.

(1) Formula [wherein, X represents a chlorine or fluorine atom, R1 is 01
- represents a C4 alkyl group, and R2 represents a methyl group. ] In the presence of a basic substance in an organic solvent with the compound shown in
Formula [wherein R3 and R4 are each independently a hydrogen atom, C3-
C6 branched or cyclic alkyl group or -COz
Rs (In the group, R5 is a hydrogen atom or a lower alkyl group)
is optionally substituted Al (in the group, R6 is a hydrogen atom,
(represents a halogen atom, lower alkyl group, lower alkenyl group, lower alkoxy group, or trifluoromethyl group)
represents. However, when X is a chlorine atom, methyl groups and alkenyl groups are excluded. ) and preferably in the presence of a basic substance at a reaction temperature of -20°C to 200°C, preferably -10°C to 1
00°C, the reaction time is 0.5 to 24 hours, preferably 1 to 12 hours, with stirring or boiling under reflux of an organic solvent to form the formula (wherein, X, R'', R2, R', R' is the same as above.) A compound represented by the following formula can be produced.

Examples of organic solvents include halogenated carbons such as methylene chloride, chlorodialum, and carbon tetrachloride, ethers such as diethyl ether, THF, and dioxane, and aromatic hydrocarbons such as benzene, toluene, and monochlorobenzene. , DMF, DMAc, NMP, HMP
Amides such as A, DMSO, DMSO2, TMSO,
Examples include, but are not limited to, aprotic polar solvents such as sulfolane.

Basic substances include NaHCO3, KHCO3, Na
2Co3. K2CO3, NaOH, KOH, LiOH
, Ca(OH)2. Mg(OH)2. Ba(OH)
Alkali or alkaline earth metal carbonates, hydroxides or Na) such as 2 (KH,.

Metal hydrides such as CaH, trimethylamine, triethylamine, N,N-dimethylaniline, 4-(N
, N-dimethyl)pyridine and other tertiary amines.

(2) Formula (wherein, X represents a chlorine or fluorine atom, RI is C0
~ Represents a C4 alkyl group. The reaction temperature of the compound represented by
The reaction is carried out at 0°C to 80°C, preferably at 0°C to room temperature, for an incubation time of 0.5 to 10 hours, preferably 1 to 5 hours to form a compound of the formula (where x and R7 are the same as above). ) in the presence of a basic substance in an organic solvent with this compound and the formula (wherein R3 and R4 are each independently a hydrogen atom, C1 to
C6 branched or cyclic alkyl group or -Co2
R' (in the group, R5 represents a hydrogen atom or a lower (in the group, R6 represents an aqueous odor atom, a halogen atom, a lower alkyl group, a lower alkenyl group, a lower alkoxy group, or a trifluoromethyl group))] amines and reaction temperature -20° to boiling point of solvent,
Preferably the temperature is -10°C to 100°C, and the reaction time is 0.5 to 100°C.
A compound represented by the formula (wherein, X, RI, RIl, and R1R4 are the same as above) is produced by reacting for 24 hours, preferably 1 to 12 hours, stirring, or under boiling and refluxing the solvent. be able to.

Here, the aprotic polar solvent is DMF.

Amides such as DMC, NMP, HMPA, and DMS
O.

Examples include DMSO2, TMSO, sulfolane, etc. Strong bases include NaHCO3, KHCO3, K
2CO3゜NaOH, KOH, LiOH, Ca(OH)
z, Mg(OH)2. Ba (alkali or alkaline earth metal carbonates such as SI-D2, hydroxides or NaH
, KH, CaH2, etc., but are not limited thereto.

In addition, the organic solvent here includes, for example, halogenated carbons such as methylene chloride, chloroform, and carbon tetrachloride;
Diethyl ether, THF, dioxannat ethers, aromatic hydrocarbons such as benzene, toluene, monochlorobenzene, DMF, DMAc, NMP, H
Amides such as MPA, DMSO, DNSO□TM
Examples include, but are not limited to, aprotic polar solvents such as SO sulfolane.

Basic substances include NaHCO, KHCO, Na
, 2CO at Co3°, , NaOH, KOH, LiOH,
Ca(OH)2. Alkali or alkaline earth metal carbonates, hydroxides, such as Mg(OH)2゜Ba(OH)2, or metal hydrides such as NaH, KH, CaH, trimethylamine, triethylamine, N,N-dimethylaniline , 4-(N,N-dimethyl)pyridine and other tertiary amines.

When the compound formula (1) of the present invention is used as an active ingredient of a fungicide for agriculture and horticulture, one or more compounds of the present invention may be used.

When the compound of the present invention is used as a fungicide for agricultural and horticultural purposes, depending on the purpose of use, it may be used as it is, or it may be mixed with an agrochemical adjuvant to enhance or stabilize the effect, or by a method commonly used in the field of agrochemical manufacturing. 1. Powders, fine granules,
It can be used in the form of granules, wettable powders, flowable preparations, emulsions, and the like.

In actual use, these various formulations can be used directly or diluted with water to a desired concentration.

The agrochemical auxiliary agents mentioned herein include carriers (diluents) and other auxiliary agents such as spreading agents, emulsifiers, wetting agents, dispersants, fixing agents, and disintegrants.

Liquid carriers include aromatic hydrocarbons such as toluene and xylene, alcohols such as methanol, butanol, and glycol, ketones such as acetone, amides such as dimethylformamide, sulfoxides such as dimethyl sulfoxide, methylnaphthalenecyclohexane, and animal and vegetable oils. , fatty acids, fatty acid esters, etc.

Solid carriers include clay, kaolin, talc, diatomaceous earth,
Examples include silica, calcium carbonate, montmorillonite, bentonite, feldspar, quartz, alumina, and sawdust.

In addition, surfactants are usually used as emulsifiers or dispersants, such as anionic surfactants such as higher alcohol sodium sulfate, stearyltrimethylammonium chloride, polyoxyethylene alkylphenyl ether, lauryl betaine, and cationic surfactants. , nonionic surfactants, and amphoteric surfactants.

As a spreading agent, polyoxyethylene nonylphenyl ether, holoxyethylene lauryl ether, etc.
Wetting agents include polyoxyethylene nonylphenyl ether, sialkyl sulfosacunate, etc., fixing agents include carboxymethyl cellulose, polyvinyl alcohol, etc., and disintegrating agents include sodium genin sulfonate, sodium lauryl sulfate, etc.

Not only can each formulation be used alone, but
It can also be used in combination with other agricultural and horticultural fungicides, insecticides, plant growth regulators, and acaricides.

The active ingredient compound content in the agricultural and horticultural fungicide of the present invention is:
It varies depending on the formulation form, method of application, and other conditions. In some cases, only the active ingredient compound may be used, but it is usually 0.2 to 95 cm (weight), preferably 0.5 to 70%.
(weight) range.

The agricultural and horticultural fungicide of the present invention has an excellent control effect when sprayed on foliage, and is suitably applied at a concentration of 10 to 4000 ppm.

The amount of the fungicide composition of the present invention to be used varies depending on the dosage form, method of use, timing, and other conditions, but for agricultural and horticultural agents, the amount of active ingredient per 10 ares is usually 10 to 300 grams, preferably 15 to 300 grams. 200 grams are used. For example, powders range from 15 to 120 grams of active ingredient per 10 are, granules range from 30 to 240 grams, and emulsions range from 40 to 250 grams. However, in special cases it is possible to exceed these ranges.
It is also possible, and sometimes even necessary, to go below.

The present invention is effective for controlling the following diseases of crops and fruit trees, but is not limited thereto.

Apple powdery mildew (71eucotricha) Pear powdery mildew (phyllactinia □) Grape powdery mildew (Jncinula necator) Persimmon powdery mildew (other side! Kozangan 1 time) Cucurbit powdery mildew (Sphaerotheca ful)
iginea) Strawberry powdery mildew
l i) Botrytis on vegetables and other plants (13otryt)
is cinerea) Vegetable Sclerotinia
inia sclerotiorum) peach gray blight (
Sclerotinia cinerea) [Effects of the Invention] The compound of the present invention is 1. a new compound not described in any literature;
In particular, it shows a high control effect when sprayed on foliage, is effective against drug-resistant bacteria, and does not have any adverse effects such as chemical damage on plants, so it can be widely used as a fungicide for agriculture and horticulture.

Next, the agricultural and horticultural fungicide of the present invention will be explained in more detail using specific examples, but the type and mixing ratio of the cosmetic auxiliary agent are not limited to these, and can be used in a wide range. Note that "parts" means "parts by weight."

Synthesis Example 1゜Production of 4-(n-butylamino)-5-fluoro-6-methyl-2-methylthiopyrimidine (compound 1'1h5): 4-chloro-5-fluoro-6-methyl-2-methylthiopyrimidine 71.5 g (7.8 mmol) of Miji in THF
Dissolve in 15ml and add 0.6 rope tylamine to it.
6 g (9,0 mmol) and triethylamine 1.
Add 53g (15mmol) and boil under reflux R.
The reaction was allowed to proceed for 0 hours. After the reaction mixture was left to cool, it was poured into water and extracted with ethyl acetate. The extract was washed with water and saturated brine, and then dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was subjected to column chromatography (silica gel, eluent n-hexane/ethyl acetate = 10/1-5/
1.57 g of 4-(n-butylamino)-5-fluoro-6-methyl-2-methylthiopyrimidine purified by step 1)
(yield 88%).

mp77-79°C Engineering l'j(z-'): 3240. 3150.
1605'HNMR (CDus + ppm) "δ0
．． 95 (t, :31(,CH3).

l, 3-1.7 (4H, m, CH, CH2n, 2.
28 (d, J=3.1Hz, 3H, CHs)+
2.49 (s, 3H, CHsS).

3.49 (td, 2H, NHCH2), 4.85 (b
r, IH.

NH).

Other alkylamines were reacted in the same manner, and all were purified by silica gel column chromatography. These results are summarized in Table 1.

Synthesis Example 2 5-fluoro-6-methyl-2-methylthio-4-(p
-Toluidino)pyrimidine (compound Nn12): 4-chloro-5-fluoro-6-methyl-2-methyb-
y-opyrimidi 71.0 g (5.2 mmol).

1.07 g of p-toluidine (10 mmol) and 1.02 g of triethylamine (IQ mmol) were added to DMAc 1
0 ml and reacted at 70° to 80°C for 9 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with dilute hydrochloric acid and then with saturated brine, and then dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by column chromatography (silica gel, eluent n-hexane/ethyl acetate - 10/1 to 5/1) to obtain the desired 5-fluoro-6-methyl-2. -methylthio-4-(p
゛-Toluidino)pyrimidine 0.95g (yield 69%)
Obtained.

mp 105-107℃ IR (Cfi/: 3240.3
145. 1600'HNMR (CD(28,pp
m): δ 2.31 (S, 3H,'C
H3).

2.33 (d, J=3.1Hz, 3H, CH8),
2.50 (S, 3H.

CHs), 6.77 (br, IH, NH), 7.
12 (d, J=8.4Hz, 2H1 benzene ring)
, 7.50 (d, J=8.4H2°2H, benzene ring).

0.18 g (yield: 15%) of 4-(N,N-diethylamino)-5-fluoro-6-methylni2-methylthiopyrimidine was obtained as a by-product from the reaction mixture. oily substance
nD 1.5479 IR (cln), 2975. 2925. 1580
'HNMR (CDcts, ppm): δ 1.
22(t, 6H.

CH3X2), 2.28(d, J=3゜6H2,
3H, CH3).

2.47 (s, 3H-CHa)-3,57(d, q
-J=l, 5 and 7.0 Hz, CH2X2).

Other anilines were reacted in the same manner and the results of purification are summarized in Table 1.

Synthesis Example 3 Production of 4-anilino-5-fluoro-6-)f-2-methylthiopyrimidine (compound N[Ll): 4-chloro-5-fluoro-6-methyl-2-methylthio-pyrimidine 75.0 Dissolve g (0,026 mol) in 2 Qmt of ethanol, and add 1' of concentrated ammonia water there.
．． Qml was added and incubated at room temperature for 10 hours, then at 80°C for 15 hours.
Allowed time to react. The reaction mixture was concentrated, diluted with water, extracted with ethyl acetate, and the extract was washed with saturated brine and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure,
The residue was purified by column chromatography (silica gel, eluent n-hexane/ethyl acetate = 20/1 to 3/1) to obtain 2.9 g (58% recovery) of the raw material, and the desired amine 0
．． 8 g (yield 42%) was obtained.

mp151-153°C IR (crn-'): 3300.3125.1
630.1590'HNMR (DMSO-do, pI
) m) : δ2.29 (d, J=3.1) (z, 3
H, CH3)l 2.46 (S,3H,CH3)1
5.9 (hr.

2H, -NH,) Synthesis Example 4゜4-chloro-5-fluoro-6-(5-fluoro-6-
Methyl-2-methylthio-4-pyrimidyl)methyl-2
-Preparation of methylthiopyrimidine: 1.92 g (10 mmol) of 4-chloro-5-fluoro-6-methyl-2-methylthio-pyrimidine.

Sodium hydride (60%, 0.4 g, 1
A mixture of 0 mmol and 20 ml of DMAc was reacted at room temperature for 2 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was thoroughly washed with water and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was subjected to column chromatography (silica gel, eluent n-hexane/ethyl acetate = 20/1 to 5/1).
) to give 1.5 g of 4-chloro-5-fluoro-6-(5-fluoro-6-methyl-2-methylthio-4-pyrimidyl)methyl-2-methylthiopyrimidine (yield: 8
6%) obtained.

mp81-83°C IR (crn), 1580, 1555.153
0.1385゜'HNMRCCDCts, ppm)
: δ 2.42 (S, 3H, CH35).

2.46 (s, 3H, CH35), 2.47 (d,
J=2.6Hz, CH,).

4.29 (t, J:1.9H2,2HCH2)13C
NMR (CDC1s, ppm): δ 14.16
(CH3), 14.36 (CH2), 17.1
8 (CHs), 33.08 (CH2), 149.3
C, C-F), 147.2, 150.6, 152.6 (
C-F).

153.7. 154.8. 165.7. 166.
519FNMR (CDCl2.ppm from
int, CF(2,): δ 141.2(IF), 14
7.1 (IF), MS: m/z+
+348 (M),
a33(M), 333(M-CH3)Ca
lcd, fore12H, (2F2N, S2+ 3
48.829 Synthesis Example 5゜4-n-butylamino-5-fluoro-6-(5-fluoro-6-methyl-2-methylthio-4-pyrimidyl)
Production of methyl-2-methylthiopyrimidine (compound K14): 4-chloro5-fluoro-6-(5-fluoro-6-
Methyl-2-methylthio-4-pyrimidyl)methyl-2
-Methylthiopyrimidine 0.93 g (2,7 mmo
l), n-butylamine 0.4 g (5,5 mmo
l), ) ethylamine 0.54 g (5,3m
mol) in 10mt of DMAc, 50-60°
The reaction was carried out at C for 4 hours. The reaction mixture was poured into water, extracted with ethyl acetate, the extractables were thoroughly washed with water, and dried over anhydrous magnesium sulfur. After distilling off the solvent under reduced pressure, it was purified by column chromatography (silica gel, eluent n-hexane/ethyl acetate = 20/1 to 5/1) to give 4-n-butylamino-5-fluoro-6-( 5-Fluoro-6-methyl-2-methylthio-4-pyrimidyl)methyl-2-
1.0 g (quantitative) of methylthiopyrimidine was obtained.

Oily substance. nDl, 5795 IR(crn-1): 3350.1600.157
8'HNMR (CD(:ts, [)pm): δ
0.941t, 3H.

CHs, 1.3-1.8 (m, 4H, (CH2)
2), 2.40 (S.

3H,CH3, 2.43 (d, 3H,CHs)
, 2.46 (s.

3H, CHs), 3.49 (td, 2H, CH2N),
4.09 (t.

2H, CH2), 5.1 (br, IH, NH).

Synthesis Example 6゜5-chloro-6-methyl-2-methylthio-4-(p-
) Preparation of pyrimidine (compound N25): 1.0 g (4.8 mmol) of 4.5-dichloro-6-methyl-2-methylthiopyrimidine and 1.0 g of triethylamine. Og (10 mmol) in DMAc
10 ml, reacted at 50 to 70°C for 8 hours, and post-treated and purified in the same manner as in Synthesis Example 2 to obtain the desired 5-chloro-6-methyl-2-methylthio-4-(1)-trifluoride. Luiginonpyrimidine 1.34 g (yield 83%).

mp 121-122°C IR (tM), 3390.2915.1575.
1545゜'HNMR (CI) Ct3+ ppm)
” δ 2.32 (S, 3H, CH3).

2.43 (S, 3H, CH3), 2.47 (S
, 3H, CH3).

7, 12 (d, 3H, -MH+benzene ring), 7.
47 (d.

2H, benzene ring).

5-chloro-4-(N,
0.14 g (yield: 12%) of N-diethylamino)-6-methyl-2-methylthiopyrimidine (compound 11!127) was obtained. Oil, nDl, 5775°IR (crn), 2965.2920.1530°'H
NMR (CDcts-pI): 1.24
(1,6H,CHsX2)-2=41 (S,3H
, CHs), 2.47 (s, 3H, CH3)
.

3.61 (q, 4H, CH2X2).

Other amines were also reacted in the same manner, and the results are summarized in Table 1.

Formulation Example I, Powder Compound Nn3, 46 parts of talc and 49 parts of clay are mixed and ground to form a powder.

Formulation example 2. A wettable powder is prepared by mixing and pulverizing 550 parts of an electrokinetic compound, 45 parts of carillion, 3 parts of higher alcohol sodium sulfate, and 2 parts of sodium ligninsulfonate.

Formulation Example 30 grains After mixing 11110 parts of agent compound N, ±35 parts of diatom, 23 parts of bentonite, 30 parts of talc and 2 parts of disintegrant,
Add 18 parts of water to evenly moisten the mixture, then extrude it through an injection molding machine, granulate it, granulate it with a granulator, and then dry it to form granules with a particle size of 0.6 to 1 fi.

Formulation Example 4 parts Microgranules 126 parts of the compound rlk are uniformly mixed and pulverized with 6 parts of polyvinyl alcohol and 9 parts of clay to form a thick powder.

Separately, 80 parts of oil well-absorbing mineral coarse powder of 74 to 105 microns is mixed in a suitable manner, and 20 parts of water is added while rotating to moisten the mixture.The above-mentioned thick powder is added, coated, and dried to form fine granules.

Formulation example 5. 1320 parts of the emulsion compound Nct was dissolved in 63 parts of xylene, and a mixture of alkylphenol ethylene oxide condensate and calcium alkylbenzenesulfonate (8:2) was added to the mixture.
17 parts were mixed and dissolved to form an emulsion.

The basic rule is to dilute it with water and use it as an emulsion.

Next, the compound of the present invention can be used against various agricultural and horticultural crop diseases.
The fact that it has an excellent pest control effect will be explained using experimental examples.

Experimental example 1. Botrytis blight control test formulation example 2. A hydrating agent containing the compound of the present invention prepared in the above was diluted with water to prepare primary leaves of kidney beans (variety: Shin-Edo).
After spraying and air-drying, pieces of mycelia of Botrytis cinerea (benzimidazole-resistant fungus) punched out using a cork pole with a diameter of 5 mm were left to stand, kept in a greenhouse, and allowed to develop. After 48 hours, the half diameter of the disease was determined. We investigated and calculated the control value.

Benomyl hydrating agent (active ingredient: methyl-1) was used as a control drug.
-(butylcarbamoyl)-2-benzimidazole carbamate) was used.

The results are shown in Table 2. The control value was calculated as follows.

Table 2 Note) A is 4-allylamino-5-chloro-6-methyl-
2-Methylthiopyrimidine (West German Patent No. 3436380
(Compounds entered in the specification) Experimental example 2. Cucumber Powdery Mildew Control Test The hydrating agent containing the compound of the present invention as an active ingredient prepared in Preparation Example 2 was diluted with water and applied to a potted cucumber at the stage of first true leaf development (cultivar 2F1 strong kagreen nodules). After spraying and air-drying, Kyu IJ 5 powdery mildew fungus (Heca f4)
The spores were inoculated and placed in a greenhouse, and two weeks later, the degree of disease onset was investigated and the control value was calculated. Benomyl hydrating agent (active ingredient: methyl-1-(butylcarbamoyl)) was used as a control drug.
-2-benzimidazole carbamate) was used. The results are shown in Table 3. The disease index and control value were calculated as follows.

A: Number of strains with severe disease onset B: Number of strains that are significantly susceptible to disease C: Number of strains with slight disease onset D=Number of healthy stocks Table 3

Claims (2)

[Claims] (1) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (1) [In the formula, X represents a chlorine or fluorine atom, R^1 represents an alkyl group of C_1 to C_4, and R^2 represents a methyl group or ▲There are mathematical formulas, chemical formulas, tables, etc.▼Represents a group, where R^3 and R^4 are each independently a hydrogen atom, a branched or cyclic alkyl group of C_1 to C_6, or COOR^5 (in the group, R
_5 is an alkyl group optionally substituted with a hydrogen atom or a lower alkyl group, a lower alkenyl group, or ▲Numerical formula,
There are chemical formulas, tables, etc. ▼ (In the group, R^6 is a hydrogen atom,
represents a halogen atom, lower alkyl group, lower alkenyl group, lower alkoxy group or trifluoromethyl group). However, when X is a chlorine atom, methyl groups and alkenyl groups are excluded. ] A pyrimidine derivative represented by (2) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (1) [In the formula, X represents a chlorine or fluorine atom, R^1 represents an alkyl group of C_1 to C_4, and R^2 represents a methyl group or ▲There are mathematical formulas, chemical formulas, tables, etc.▼Represents a group, where R^3 and R^4 are each independently a hydrogen atom, a branched or cyclic alkyl group of C_1 to C_6, or COOR^5 (in the group, R^ 5 is a hydrogen atom or an alkyl group optionally substituted with a lower alkyl group), a lower alkenyl group, or ▲
There are mathematical formulas, chemical formulas, tables, etc.▼ (In the group, R^6 represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkenyl group, a lower alkoxy group, or a trifluoromethyl group). However, when X is a chlorine atom, methyl groups and alkenyl groups are excluded. ] An agricultural and horticultural fungicide characterized by containing a pyrimidine derivative represented by the following as an active ingredient.