JPH0649039A - Pyrimidine derivative, herbicide and fungicide for agricultural and horticultural use - Google Patents

Abstract

PURPOSE:To provide a new pyrimidine derivative usable as a herbicide or an agricultural and horticultural fungicide having high selectivity to crops and high safety and exhibiting remarkable effect by the use of a decreased amount of the compound. CONSTITUTION:The compound of formula [R<1> and R<2> are H, alkyl, alkenyl, alkynyl, amino, halogen, CN, OR<9>, SR<10>, OCOR<11> (R<9> to R<11> are H, alkyl, phenyl, etc.), etc.; R<3> and R<5> are H, halogen, alkyl, alkenyl, alkynyl, phenyl, cycloalkyl, etc.; R<4> is H, alkyl, alkenyl, phenyl, cycloalkyl, COOR<23>, COR<24> (R<23> and R<24> are H, alkyl, phenyl, etc.), etc.; R<6> and R<7> are H, halogen, alkyl, phenyl, S(O)qR<28> (q is 0-2; R<28> is H, alkyl, phenyl, etc.), etc.; R<8> is H, halogen, alkyl, phenyl, S(O)rR<33>, OR<34> (r is 0-2; R<33> and R<34> are H, alkyl, phenyl, etc.), etc.], e.g. 2- benzoyl-4-methylthio-6-trifluoromethylpyrimidine.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel pyrimidine derivative, a herbicide and an agricultural / horticultural fungicide.

[0002]

2. Description of the Related Art In the cultivation of agricultural and horticultural crops, many herbicides have come to be used for controlling weeds, which have required a great deal of labor, and a large number of control agents have been used against pests and diseases of crops. It is used, but its efficacy is insufficient, its use is restricted by the emergence of drug-resistant pathogens and pests, it causes medicinal damage to plants, and it remains in the environment and contaminates. However, there is a demand for the development of a drug that can be safely used with a lower dose and a reliable effect. Compounds similar to the compound of the present invention are disclosed in EP461079, WO91 / 10653, J.
Chem. Res. (S), 1977 , 186, etc.

[0003]

DISCLOSURE OF THE INVENTION The object of the present invention is a herbicide or agricultural / horticultural sterilization which can be synthesized industrially advantageously, is highly effective with a lower dose, is highly safe and has good selectivity with crops. It is to provide a novel compound that can be used as an agent.

[0004]

The present invention has the general formula (I)

[Chemical 4] [In the formula, R ¹ and R ² are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted amino, halogen, Cyano, OR ⁹ (in the formula, R ⁹
Represents hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, or optionally substituted cycloalkyl. ), SR ¹⁰ (wherein R ¹⁰ is hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl,
It represents optionally substituted phenyl or optionally substituted cycloalkyl. ), OCOR ¹¹ (wherein, R ¹¹ is hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl,
It represents optionally substituted phenyl or optionally substituted cycloalkyl. ), Or taken together as oxo, thioxo, optionally substituted alkylene, optionally substituted alkylidene, ═NR ¹² (wherein R ¹²
Is hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, optionally substituted cycloalkyl, mono- or di-substituted Represents an optionally substituted amino group. ), ═NOR ¹³ (wherein R ¹³ is hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, substituted or not) Represents an optionally substituted cycloalkyl or an optionally substituted acyl).
Or may together form a carbocycle or a heterocycle, and R ³ and R ⁵ are each independently hydrogen, halogen, optionally substituted alkyl, or optionally substituted alkenyl. , Optionally substituted alkynyl, optionally substituted phenyl, optionally substituted cycloalkyl, S (O) mR ¹⁴ (wherein R ¹⁴
Represents optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, optionally substituted cycloalkyl, and m is 0, 1 or Represents 2. ), N
R ¹⁵ R ¹⁶ (in the formula, R ¹⁵ and R ¹⁶ are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl,
It may represent optionally substituted phenyl, optionally substituted cycloalkyl, or may together form a ring. ), OR ¹⁷ (wherein, R ¹⁷ is hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, optionally substituted Represents a good cycloalkyl), cyano, COOR ¹⁸ (wherein R ¹⁸ is hydrogen,
Represents an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted phenyl, and an optionally substituted cycloalkyl. ), CONR ¹⁹ R ²⁰ (wherein R ¹⁹ , R
²⁰ is independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, optionally substituted cycloalkyl Represent ),
PZ (OR ²¹ ) (OR ²² ) (In the formula, Z represents O or S, and R ²¹ and R ²² represent the same or differently substituted alkyl or optionally substituted phenyl. And R ⁴ represents hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, optionally substituted cycloalkyl. , COOR ²³
(In the formula, R ²³ is hydrogen, an optionally substituted alkyl,
Represents alkenyl which may be substituted, alkynyl which may be substituted, phenyl which may be substituted, and cycloalkyl which may be substituted. ), COR
²⁴ (In the formula, R ²⁴ is hydrogen, alkyl which may be substituted, alkenyl which may be substituted, alkynyl which may be substituted, phenyl which may be substituted, cycloalkyl which may be substituted) ), CON
R ²⁵ R ²⁶ (in the formula, R ²⁵ and R ²⁶ are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, or optionally substituted Good phenyl, optionally substituted cycloalkyl, S (O) _p R ²⁷ (in the formula, R ²⁷
Represents hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, optionally substituted cycloalkyl, and p is 0, Represents 1 or 2. And R ⁶ and R ⁷ are each independently hydrogen, halogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, Optionally substituted cycloalkyl, S (O) qR ²⁸ (wherein R ²⁸ is optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted Represents phenyl, optionally substituted cycloalkyl, q represents 0, 1 or 2), OR ²⁹
(In the formula, R ²⁹ is hydrogen, optionally substituted alkyl,
Represents alkenyl which may be substituted, alkynyl which may be substituted, phenyl which may be substituted, and cycloalkyl which may be substituted. ), COOR ³⁰
(In the formula, R ³⁰ is hydrogen, an optionally substituted alkyl,
Represents alkenyl which may be substituted, alkynyl which may be substituted, phenyl which may be substituted, and cycloalkyl which may be substituted. ), CONR ³¹
R ³² (in the formula, R ³¹ and R ³² are each independently hydrogen, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, or an optionally substituted phenyl. , Represents an optionally substituted cycloalkyl), represents a mono- or di-substituted amino group, and nitro, and R ⁸ is the same or different and is hydrogen, halogen or an optionally substituted alkyl. ,
Optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, optionally substituted cycloalkyl, S (O) rR ³³ (wherein R ³³ is substituted) Represents alkyl which may be substituted, alkenyl which may be substituted, alkynyl which may be substituted, phenyl which may be substituted, cycloalkyl which may be substituted, and r represents 0, 1 or 2. , OR ³⁴ (in the formula, R ³⁴ is hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, optionally substituted Represents cycloalkyl), COOR ³⁵ (in the formula, R ³⁵ is hydrogen, alkyl which may be substituted, alkenyl which may be substituted,
Represents alkynyl which may be substituted, phenyl which may be substituted, and cycloalkyl which may be substituted. ), CONR ³⁶ R ³⁷ (wherein R ³⁶ and R ³⁷ are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, or substituted). Optionally phenyl, optionally substituted cycloalkyl), optionally mono- or di-substituted amino group, nitro, cyano, and n represents 0, 1, 2 or 3. ] The pyrimidine derivative represented by this, a herbicide, and an agricultural and horticultural fungicide.

The method for producing the compound of the present invention is as follows.

[Chemical 5]

[0006]

[Chemical 6] [In the formula, R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ ,
R ¹⁰ and n have the same meanings as described above, and R ′ ⁵ is hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, Represents an optionally substituted cycloalkyl, R ″ ⁵ is S (O) mR ¹⁴ , NR ¹⁵ R ¹⁶ , O
R ¹⁷ (in the formula, R ¹⁴ , NR ¹⁵ , R ¹⁶ , R ¹⁷ , and m have the same meanings as described above, provided that R ¹⁷ is not hydrogen), cyano, R ³⁸ represents alkyl, and R ³⁹ Represents optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, X represents halogen and Y represents a leaving group. ]

In the above reaction a, the raw material amidine or its organic salt such as a mineral acid or a carboxylic acid and the other raw material, a carbonyl compound, are allowed to stand at room temperature to room temperature in the presence of a base.
The reaction is carried out at the boiling point of the solvent for 1 to 48 hours. As the solvent, alcohols such as ethanol, TH
Examples thereof include ethers such as F, hydrocarbons such as benzene and toluene, DMF and the like, or a mixture thereof.
Examples of the base include alcoholates of lower alcohols such as sodium methylate and potassium ethylate, inorganic bases such as potassium carbonate and sodium hydroxide, and organic bases such as DBU.

The above reaction b is carried out in a solvent in the presence of an oxidizing agent,
The reaction is carried out at room temperature to the boiling point of the solvent. Examples of the solvent include water, ethers such as dioxane, hydrocarbons such as benzene and toluene, and mixed homogeneous solvents or mixed bilayer solvents thereof. KMnO as oxidizing agent
₄ , K ₂ Cr ₂ O ₇ , SeO _{2 and the} like can be mentioned.

The above reaction c is carried out in the absence of a solvent or in the presence of a halogenating agent at room temperature to the boiling point of the solvent. Examples of the solvent include halogenated hydrocarbons such as methylene chloride and chloroform, hydrocarbons such as benzene and toluene, and a mixture thereof.
Examples of the halogenating agent include POX ₃ , PCl ₅ , and PX ₃ (wherein X represents halogen).

The above reaction d is carried out in the presence of a base at room temperature to the boiling point of the solvent for several minutes to 24 hours. As the solvent, alcohols such as ethanol,
Examples thereof include ethers such as THF and dioxane, hydrocarbons such as benzene and toluene, DMF and the like, or a mixture thereof. Examples of the base include alcoholates of lower alcohols such as sodium methylate and potassium ethylate, inorganic bases such as potassium carbonate and sodium hydroxide, D
Examples thereof include organic bases such as BU.

[0011]

EXAMPLES The present invention will be further described with reference to examples.
The structure was determined by IR, NMR, MS and the like. Example 1 2- (4-chlorophenylmethyl) -4-hydroxy-
6-trifluoromethylpyrimidine (Compound No. II-
5) Sodium ethylate 1.87 g ethanol 50 ml
To the solution was added 4-chlorobenzylamidine hydrochloride (4.7 g), and trifluoroacetylacetoacetic acid ethyl ester (4.64 g) was added, and the mixture was reacted under reflux for 10 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure, diluted hydrochloric acid was added to the residue, and the precipitated crystals were filtered and washed with water. Further, the filtrate was extracted with ether, dried over magnesium sulfate, and then the solvent was distilled off to obtain crystals. The obtained crystals are combined and dried,
4.25 g of the desired product was obtained.

Example 2 2- (4-chlorobenzoyl) -4-hydroxy-6-
Trifluoromethylpyrimidine (Compound No. I-81) 2- (4-chlorophenylmethyl) -4-hydroxy-
4.25 g of 6-trifluoromethylpyrimidine was dissolved in 40 ml of dioxane and 5 ml of water, and selenium dioxide 1.
98 g was added and the mixture was reacted under reflux for 15 hours. After cooling, the insoluble matter was filtered and the filtrate was extracted with ethyl acetate. The organic layer was washed with water and then dried over magnesium sulfate, the solvent was distilled off to obtain a solid substance, which was washed with ether to obtain 2.5 g of a target crystal. Melting point 174-5 ° C

Example 3 4-chloro-2- (4-chlorobenzoyl) -6-trifluoromethylpyrimidine (Compound No. I-79) 2- (4-chlorobenzoyl) -4-hydroxy-6-
10 ml of phosphorus oxychloride was added to 2.1 g of trifluoromethylpyrimidine, and the mixture was reacted under reflux for 2 hours. After completion of the reaction, the reaction solution was poured into water and extracted with methylene chloride. The organic layer was washed with water, dried over magnesium sulfate, the solvent was distilled off, and the obtained residue was purified by silica gel column chromatography to obtain 1.55 g of the oily desired product. n _D ^22.9 = 1.5
554

Example 4 2-benzoyl-4-methylthio-6-trifluoromethylpyrimidine (Compound No. I-10) 2.0 g of 2-benzoyl-4-chloro-6-trifluoromethylpyrimidine was dissolved in 20 ml of tetrahydrofuran. Then, 6.02 g of a 15% methyl mercaptan sodium salt aqueous solution was added dropwise under ice-water cooling. After reacting for 2 hours at room temperature, diluted hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate, the solvent was distilled off, and the obtained residue was purified by silica gel column chromatography to obtain 1.89 g of the desired crystal. Melting point 59-60 ° C

Example 5 2-Benzoyl-4-methylsulfonyl-6-trifluoromethylpyrimidine (Compound No. I-11) 1.38 g of 2-benzoyl-4-methylthio-6-trifluoromethylpyrimidine was dissolved in 30 ml of methanol. Then, after adding a catalytic amount of sodium tungstate, 1.57 g of 30% hydrogen peroxide aqueous solution was added dropwise at room temperature, and then reacted for 15 hours. The reaction mixture was concentrated to 1/3 under reduced pressure, dissolved in ethyl acetate, washed with water, washed with aqueous sodium thiosulfate solution, washed with saturated brine, and dried over magnesium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography to obtain 1.06 g of the desired crystal. Melting point 1
17-8 ° C

Example 6 2- (3-chlorobenzoyl) -4-methoxy-6-trifluoromethylpyrimidine (Compound No. I-75) 4-chloro-2- (3-chlorobenzoyl) -6-trifluoromethyl Pyrimidine 1.0 g, methanol 1
Dissolve in 0 ml and let 28% sodium methylate at room temperature.
0.72 g of a methanol solution was added dropwise. After reacting at room temperature for 1 hour, water was added and the mixture was neutralized with diluted hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and the solvent was concentrated. The obtained residue is purified by silica gel column chromatography to give 0.93 of the desired product as an oil.
g was obtained. n _D ^22.9 = 1.5308

Example 7 2- (2-chlorobenzoyl) -4-methylamino-6
-Trifluoromethylpyrimidine (Compound No. I-2
5) 4-chloro-2- (2-chlorobenzoyl) -6-trifluoromethylpyrimidine 0.6 g was added to methanol 1
It was dissolved in 0 ml, and 0.43 g of 40% methylamine methanol solution was added dropwise at room temperature. After reacting at room temperature for 1 hour, water was added and the mixture was neutralized with diluted hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and the solvent was concentrated. The obtained residue was purified by silica gel column chromatography to obtain 0.30 g of the objective crystal. Melting point 111-2 ° C

Representative examples of the compounds of the present invention, including the above-mentioned Examples, are shown in Tables 1 and 2. In the table, the melting point is shown in [] of the physical property values.

[0019]

[Table 101]

[0020]

[Table 102]

[0021]

[Table 103]

[0022]

[Table 104]

[0023]

[Table 105]

[0024]

[Table 106]

[0025]

[Table 107]

[0026]

[Table 108]

[0027]

[Table 109]

[0028]

[Table 110]

[0029]

[Table 111]

[0030]

[Table 112]

[0031]

[Table 113]

[0032]

[Table 114]

[0033]

[Table 115]

[0034]

[Table 116]

[0035]

[Table 117]

[0036]

[Table 118]

[0037]

[Table 119]

[0038]

[Table 120]

[0039]

[Table 121]

[0040]

[Table 122]

[0041]

[Table 123]

[0042]

[Table 124]

[0043]

[Table 125]

[0044]

[Table 126]

[0045]

[Table 127]

[0046]

[Table 128]

[0047]

[Table 129]

[0048]

[Table 130]

[0049]

[Table 131]

[0050]

[Table 132]

[0051]

[Table 133]

[0052]

[Table 134]

[0053]

[Table 135]

[0054]

[Table 136]

[0055]

[Table 137]

[0056]

[Table 138]

[0057]

[Table 139]

[0058]

[Table 140]

[0059]

[Table 141]

[0060]

[Table 142]

[0061]

[Table 143]

[0062]

[Table 144]

[0063]

[Table 145]

[0064]

[Table 146]

[0065]

[Table 201]

[0066]

[Table 202]

[0067]

[Table 203]

[0068]

[Table 204]

[0069]

[Table 205]

[0070]

[Table 206]

[0071]

[Table 207]

[0072]

[Table 208]

[0073]

[Table 209]

[0074]

[Table 210]

[0075]

[Table 211]

[0076]

[Table 212]

[0077]

[Means for Solving the Problems]

[Herbicides and fungicides] The compound of the present invention exhibits high herbicidal activity under both upland conditions and both soil treatment and foliage treatment.
Especially in soil treatment, it shows high efficacy against various field weeds such as Crabgrass, Aquino ecologsa, and Aedes serrata, corn,
It also contains compounds that show selectivity for crops such as wheat and soybeans. The compounds of the present invention also include compounds having excellent herbicidal activity against weeds of paddy weeds such as Nobie, Tamagawai and Omodaka, and showing selectivity for rice. Furthermore, the compound of the present invention can be applied to control weeds in orchards, lawns, railroad ends, vacant lots and the like.

Since the compound of the present invention has an excellent bactericidal activity against a wide variety of filamentous fungi, it is used for controlling various diseases caused during cultivation of agricultural and horticultural crops including flowers, turf and grass. You can do it. For example, sugar beet leaf spot ( Cercospora betico)
la ), Peanut leaf spot ( Mycosphaere)
Lla arachidis ), Black spot disease ( Mycosp)
haerella berkeleyi ), powdery mildew of cucumber ( Sphaerotheca fuligi)
nea ), vine blight ( Mycosphaerella )
melonis ), sclerotinia ( Sclerotinia )
sclerotiorum ), Botrytis cinerea ( Botry)
tis cinerea ), scab ( Cladospo )
riumcucumerinum), tomato gray mold disease (Botrytis cinerea), Leaf blight (Cladosporium fulvum), eggplant gray mold disease (Botrytis cinerea), black blight (Corynespora melongena
e ), powdery mildew ( Erysiphe cichora)
cearum ), strawberry gray mold ( Botryti)
s cinerea ), powdery mildew ( Sphaerot )
heca humuli ), gray rot of onion ( B
otrytis allii ), Botrytis cinerea ( Botr
ytis cinerea ), Sclerotinia sclerotioru
m ), Gray mold ( Botrytis cinere)
a ), powdery mildew of apple ( Podochaera)
leucotricha ), scab ( Venturia )
inaequalis), Monilia disease (Monili
niamal ), powdery mildew of oysters ( Phylllac)
tinia kakicola ), anthracnose ( Gloeo )
sporium kaki ), horn spot leaf disease ( Cerco
spora kaki ), peach and sweet cherry scab ( M
onilinia fructicola), grape Botrytis (Botrytis cinerea), powdery mildew (Uncinula necator), ripe rot (Glomerella cingulata), pear scab (Venturia nashicol
a ), scab ( Gymnosporangium as
iaticum ), Black spot ( Alternaria k)
ikuchuiana ), tea leaf spot ( Pestalo)
tia theae ), anthracnose ( Colletotri )
chumtheae-sinensis ), citrus scab ( Elsinoe fawcetti ), blue mold ( Penicillium italicum ),
Green mold ( Penicillium digitatu)
m ), Gray mold ( Botrytis cinere)
a ), powdery mildew of barley ( Erysiphegra
minis f. sp. hordei ), naked smut ( U
stilagonuda ), Fusarium head blight of wheat ( Gib
berella zeae ), red rust ( Puccin )
ia recondita ), leaf spot ( Cochlio )
bolus sativus ), eye blight ( Pseudo )
cercosporella herpotricho
des ), blight ( Leptosphaeria n
odorum ), powdery mildew ( Erysiphe gr)
aminis f. sp. tritici ), red snow rot ( Micronectorella nivali)
s ), rice blast ( Pyricularia or
yzae ), blight ( Rhizoctonia sol)
ani ), Gibberella fujik
uroi ), sesame leaf blight ( Cochliobolus
miyabeanus), tobacco Rot (Scler
otinia sclerotiorum ), powdery mildew ( Erysiphe cichoracearu)
m ), tulip gray mold ( Botrytis)
cinerea ), bentgrass snow rot large grain sclerot ( S)
clerotinia borealis ), powdery mildew of orchardgrass ( Erysiphe gram)
inis ), soybean purpura ( Cercospora)
Kikuchii ), potato, tomato plague ( Ph
ytophthora infestans ), downy mildew of cucumber ( Pseudoperonospora c)
ubensis ), downy mildew of grapes ( Plasmopa
ra viticola) it can be used for the control of such.

In addition, Botrytis c. Fungi which are resistant to benzimidazole fungicides (eg, thiophanate methyl, benomyl, carbendazim)
inea ) and sugar beet leaf spot fungus ( Cercospo)
ra beticola ), an apple scab ( Vent)
uria inaequalis ), pear scab ( V
The compounds of the present invention are also effective against enturia nashicola as in the case of susceptible bacteria. Further, the compounds of the present invention are also effective against Botrytis cinerea, which is resistant to dicarboximide fungicides (eg, vinclozolin, procymidone, iprodione), as well as susceptible bacteria. The compound of the present invention can be used as an antifouling agent for preventing aquatic organisms from adhering to underwater contact objects such as ship bottoms and fishnets, and also as a general antifungal agent for household and industrial use. It can also be used.

When the compound of the present invention thus obtained is actually applied, it contains one or more of the compounds represented by the above general formula (I) as an active ingredient, and has the same composition as a usual pesticide. Has a morphology. That is, the active ingredient compound is generally mixed with a carrier in an appropriate amount to prepare a wettable powder, an emulsion, a granule, a powder,
It is used by formulating it in the form of water solvent, flowable agent, etc.
When a solid agent is intended as an additive and a carrier,
Soybean powder, vegetable powder such as wheat flour, diatomaceous earth, pyroxene, gypsum, talc, pyrophyllite, clay, white carbon (silica), bentonite, mineral oil, vegetable oil and other fine mineral powders are used. For liquid dosage forms, use kerosene, mineral oil, petroleum, solvent naphtha, benzene, xylene, cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, alcohol, acetone, mineral oil, vegetable oil, water, etc. as the solvent. . If necessary, a surfactant may be added in order to obtain a uniform and stable form in these preparations.

The concentration of the active ingredient in the herbicide and fungicide of the present invention varies depending on the form of the above-mentioned preparation. For example, in the wettable powder, it is 5 to 70%, preferably 10%. -30%, in emulsion 3-70%,
Preferably 5 to 20%, in granules 0.01 to 3
A concentration of 0%, preferably 0.05% to 10% is used.

The wettable powder and emulsion thus obtained are diluted with water to a predetermined concentration to give a suspension or emulsion, and powders and granules are used as they are as herbicides before germination of weeds or After germination, the soil or weeds are sprayed or mixed. In applying the herbicide of the present invention, an appropriate amount of 0.1 g or more of the active ingredient is applied per 10 ares. In the case of a fungicide, it is used by a method of spraying it on plants. Further, the compound of the present invention can be used as a mixture with a known fungicide, insecticide, acaricide, herbicide, plant growth regulator and the like. This not only saves labor, but also can expect a higher effect due to the synergistic action of the mixed drugs. In that case, a combination with a plurality of known compounds is also possible.

Typical examples of herbicides, fungicides, insecticides, acaricides and plant growth regulators which can be used by mixing with the compound of the present invention are shown below. [Herbicides] Bentocarb, Molinate, MY-93
Carbamate herbicides such as [S- (2,2-dimethylbenzyl) 1-piperidyl carbothioate], thiocarbamate herbicides, acid amide herbicides such as butachlor, pretilachlor and mefenacet, diphenyl ethers such as clomethoxynil and bifenox. Herbicides,
Triazine herbicides such as atrazine and cyanazine, sulfonylurea herbicides such as bensulfuron-methyl, pyrazosulfuron-ethyl, chlorsulfuron and sulfometuron-methyl, phenoxyalkanecarboxylic herbicides such as MCP and MCPB, diclohop-methyl, etc. Phenoxyphenoxypropionic acid herbicides, imidazolinone herbicides such as imazaquin, pyridyloxyphenoxypropionic acid herbicides such as fluazifop-butyl,
Benzoylaminopropionic acid herbicides such as benzoylpropethyl and furanpropethyl, imidazolinone herbicides such as imazaquin, and others such as piperophos, dimuron, bentazone, difenzocoat, naproanilide, HW-52 (4-ethoxymethoxy) Benz-2,3-dichloroanilide), KNW-242
[1- (3-methylphenyl) -5-phenyl-1H-
1,2,4-triazole-3-carboxysamide],
Cyclohexanedione-based herbicides such as quinclorac (3,7-dichloro-8-quinolinecarboxylic acid), setoxydim, and alloxydim-sodium.

[Fungicide] Captan, Folpet, Thiuram, Zineb, Manneb, Mancozeb, Propineb,
Polycarbamate, chlorothalonil, quintozene, captafol, iprodione, prosimidone, vinclozolin, fluoroimide, thymoxanil, mepronil, flutolanil, pencyclone, oxycarboxyne, fosetylaluminum, propamocarb, triadimefon, triadimenol, propiconazole, diclobutrazol, Bitertanol, hexaconazole, microbutanyl, flucirazole, etaconazole, fluotrimazole, flutriafen, penconazole, diniconazole, cyproconazole, phenalimol, triflumizole, prochloraz, imazalil,
Pefurazoate, tridemorph, fenpropimorph,
Triphorine, butiobate, pyriphenox, anilazine, polyoxine, metalaxyl, oxadixyl,
Furaraxil, isoprothiolane, probenazole, pyrrolenitrin, blasticidin S, kasugamycin, validamycin, dihydrostreptomycin sulfate, benomyl, carbendazim, thiophanatemethyl, hymexazole, basic copper chloride, basic copper sulfate, fentin acetate, triphenyl hydroxide Tin, dietofencarb, metasulfocarb, quinomethionate, vinapacryl, lecithin, baking soda, dithianon, zinocap, phenaminosulf, diclomedine, guazatine, dozine, IBP, edifenphos, mepanipyrim, ferimzone, trichlamide, metasulfocarb, fluazinam, etoquinolac, etquinolac, etoquinolac. Pyroquilon, teclophthalam, thalide.

[Insecticidal / Acaricide] Chlorbenzilate,
Chlorpropylate, Proclonol, Phenisobromolate, Dicofol, Zinobuton, Chlorphenamidine,
Amitraz, BPPS, PPPS, benzomate, hexithiazox, fenbutatin oxide, polynactin, thioquinox, CPCBS, tetradiphone, isoxathione, avermectin, lime polysulfide, clofentezine, flubenzmin, flufenoxuron, BCPE,
Cyhexatin, pyridaben, fenpyroximate, fenthion, fenitrothion, diazinon, chlorpyrifos, ESP, vamidothion, phenthoate, dimethoate, formothion, malathion, Jipu telex, thiometon, phosmet, Menazon, dichlorvos, acephate, EPBP, dialifor, methyl parathion, oxy Jimeton methyl, ethion , Pyraclofos, Monocrotophos, Methomil Monocrotophos, Aldicarb, Propoxur, BPMC, MTMC,
Nac, Cartap, Carbosfan, Benfuracarb, Pirimicarb, Etofencarb, Phenoxycarb, Permethrin, Cypermethrin, Decamethrin,
Fenvalerate, fenpropasulin, pyrethrin,
Allethrin, tetramethrin, resmethrin, dimethrin, propasulin, bifenthrin, prothrin, fluvalinate, cyfluthrin, cyhalothrin, flusilinate, etofenprox, cycloprothrin, tralomethrin, silaneofane, diflubenzuron, chlorfluazuron, triflumuron, teflubenzuron,
Buprofezin, machine oil.

[Plant growth regulator] Gibberellins (eg, gibberellin A ₃ , gibberellin A ₄ , gibberellin A ₇ ) I
AA, NAA, Inabenfide, Ethephon, Chlormequat, Uniconazole, Paclobutrazol.

[0087]

【Example】

[Herbicides, fungicides] Next, some examples of the composition of the present invention will be shown, but the additives and addition ratios should not be limited to these examples, and can be varied in a wide range. Is. Parts in the formulation examples indicate parts by weight.

Example 8 Wettable powder Compound of the present invention 40 parts Diatomaceous earth 53 parts Higher alcohol sulfate ester 4 parts Alkylnaphthalene sulfonate 3 parts The above ingredients are mixed evenly and finely ground to obtain 40
% Of wettable powder is obtained.

Example 9 Wettable powder Compound of the present invention 20 parts White carbon 20 parts Diatomaceous earth 52 parts Sodium alkyl sulfate 8 parts The above components are uniformly mixed and finely pulverized to obtain a wettable powder containing 20% of the active ingredient.

Example 10 Emulsion Compound of the present invention 30 parts Xylene 33 parts Dimethylformamide 30 parts Polyoxyethylene alkylallyl ether 7 parts If the above ingredients are mixed and dissolved, an emulsion containing 30% of the active ingredient is obtained.

Example 11 Emulsion Compound of the present invention 20 parts Xylene 55 parts Dimethylformamide 15 parts Polyoxyethylene phenyl ether 10 parts The above components are mixed and dissolved to obtain an emulsion containing 20% of the active ingredient.

Example 12 Granules Compound of the present invention 5 parts Talc 40 parts Clay 38 parts Bentonite 10 parts Sodium alkyl sulfate 7 parts The above components are uniformly mixed and finely pulverized, and then the diameter is 0.5 to 1.
Granulate into 0 mm granules to obtain granules containing 5% of the active ingredient.

Example 13 Granules Compound of the present invention 5 parts Clay 73 parts Bentonite 20 parts Dioctyl sulfosuccinate sodium salt 1 part Sodium phosphate 1 part The above ingredients are well pulverized and mixed, and water is added and thoroughly kneaded.
Granulate and dry to obtain granules with 5% active ingredient.

Example 14 Powdered compound of the present invention 10 parts Talc 89 parts Polyoxyethylene alkylallyl ether 1 part The above ingredients are mixed evenly and finely pulverized to obtain the active ingredient 10
% Powder is obtained.

Example 15 Suspension Compound of the present invention 10 parts Sodium lignin sulfonate 4 parts Sodium dodecylbenzene sulfonate 1 part Xanthan gum 0.2 parts Water 84.8 parts The above components are mixed until the particle size becomes 1 micron or less. Wet milling gives a suspension with 10% active ingredient.

[0096]

【The invention's effect】

[Herbicides and fungicides] Next, test examples relating to the effects of the herbicides of the present invention will be shown. Test Example 1 Upland soil treatment test A plastic pot having a surface area of 250 cm ² was filled with upland soil, and as seeds of weeds, the seeds of crabgrass, Aquinoenologosa, and Amaranthus serrata were sown and covered with 0.5 cm of soil. The next day, the diluting solution of the wettable powder shown in Example 9 was added,
The active ingredient was uniformly sprayed on the soil so that the amount of the active ingredient was 200 g per 10 a, and 20 days after the treatment, the herbicidal effect was investigated according to the following inspection criteria, and the results are shown in Table 3.

[0097]

[Table 3] Survey criteria Slaughter rate Slaughter index 0% 0 20-29% 2 40-49% 4 60-69% 680 80-89% 8 100% 10 Also 1, 3, 5, 7, 9 The numerical values of 0 indicate intermediate values between 0 and 2, 2 and 4, 4 and 6, 6 and 8, and 8 and 10, respectively.

[0098]

[Equation 1]

[0099]

[Table 4]

Test Example 2 Paddy Soil Treatment Test Pads of 150 cm ² were filled with paddy soil, and seeds of rice, novier, cypress, and odaka were sown and lightly covered with soil. The next day, maintaining a water depth of 2 to 3 cm, the granules of each compound were treated in a predetermined dose and grown in a greenhouse. The herbicidal effect of each weed was investigated 3 weeks after the chemical treatment according to the following criteria,
The results shown in Table 4 were obtained.

[0101]

[Table 5]

Next, it is shown in Test Examples that the compound of the present invention is useful as an active ingredient of various plant disease controlling agents. The control effect is the disease state of the test plant at the time of the survey, that is, the degree of growth of lesions and fungi that appear on leaves, stems, etc. is visually observed,
"5" if no bacterial stains or lesions are observed, "4" if about 10% is admitted, "3" if about 25% is admitted, "2" if about 50% is admitted, about 75% compared to the untreated area "1" if admitted, "0" if there is no difference from the disease state in the untreated area
Is evaluated in 6 levels of 0 to 5, 0, 1, 2, 3,
Shown by 4 and 5.

Test Example 3 Apple Scab Disease Control Test (Prevention Test) Apple seedlings (cultivar "Kunimitsu", 3
~ 4 leaf stage), a drug solution of the compound of the present invention having a predetermined concentration is sprayed and air-dried, and then the scab of apple scab (Ventu) is applied.
ria inaequalis) inoculated with conidia of
After being kept in a room of high humidity at 20 ° C. for 2 weeks under illumination (light / dark repetition), the control effect was investigated. The results are shown in Table 5.

[0104]

[Table 6]

Test Example 4 Grape Downy Mildew Control Test Leaves planted in the open field (cultivar "Kaiji", third grader) were cut out and punched into a disk having a diameter of 30 mm, which was designated as a wettable powder of the compound of the present invention. A suspension of zoosporangium of Plasmopara viticola was spray-inoculated into a drug solution having a concentration and kept in a humid chamber at 20 ° C. under illumination, and the condition of disease onset was examined 10 days after the inoculation. The results are shown in Table 6.

[0106]

[Table 701]

[0107]

[Table 702]

[0108]

[Table 703]

[0109]

[Table 704]

[0110]

[Table 705]

Test Example 5 Cucumber downy mildew control test (prevention test) Cucumbers (cultivar Sagamihanjiro) grown for about 3 weeks in a greenhouse
The seedlings were sprayed with a chemical solution of a wettable powder of the compound of the present invention at a predetermined concentration on the back surface of a cucumber leaf, air-dried, and then the present bacterium ( Pseudoperonospor) collected from a leaf of cucumber downy mildew.
a cubensis ) zoosporangia suspension was spray-inoculated and kept in an inoculation box at 25 ° C and 100% humidity. Inoculation 2
After a day, the treated cucumber seedlings are heated to room temperature of 23 to 26 ° C. and humidity of 70.
% Or more of the greenhouse and the control effect was investigated after 2 days. The results are shown in Table 7.

[0112]

[Table 801]

[0113]

[Table 802]

Test Example 6 Tomato Late Blight Control Test (Prevention Test) Tomatoes raised in unglazed pots (variety: large Fukuju, 5-6)
Leaf stage) The seedlings were sprayed with a chemical solution of the wettable powder of the compound of the present invention at a predetermined concentration. After spraying, the plants were air-dried at room temperature and pre-cultured on potato tubers, Phytophthora infestans ( Phyto
Phthorainfestans ) was spray inoculated with a suspension of zoosporangium. After inoculation, the plants were kept at 20 ° C. and high humidity for 4 days, and then the disease state was investigated to determine the control effect. The results are shown in Table 8.

[0115]

[Table 9]

 ─────────────────────────────────────────────────── ─── Continuation of front page (72) Inventor Shigeo Yamada 345 Yanagicho, Takada, Odawara, Kanagawa Nihon Soda Co., Ltd. Odawara Research Institute (72) Inventor, Takashi 345, Yanagicho, Takada, Odawara, Kanagawa Nippon Soda Co., Ltd. Inside the Odawara Research Center (72) Inventor Akira Hashimoto Inside the Odawara Research Center, Nippon Soda Co., Ltd. 345, Takada, Odawara City, Kanagawa Prefecture (72) Inventor Susumu Shimoda 345 Inside the Odawara Research Center, Odawara City, Kanagawa Prefecture

Claims (3)

[Claims] 1. A compound represented by the general formula (I): [In the formula, R ¹ and R ² are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted amino, halogen, Cyano, OR ⁹ (in the formula, R ⁹
Represents hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, or optionally substituted cycloalkyl. ), SR ¹⁰ (wherein R ¹⁰ is hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl,
It represents optionally substituted phenyl or optionally substituted cycloalkyl. ), OCOR ¹¹ (wherein, R ¹¹ is hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl,
It represents optionally substituted phenyl or optionally substituted cycloalkyl. ), Or taken together as oxo, thioxo, optionally substituted alkylene, optionally substituted alkylidene, ═NR ¹² (wherein R ¹²
Is hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, optionally substituted cycloalkyl, mono- or di-substituted Represents an optionally substituted amino group. ), ═NOR ¹³ (wherein R ¹³ is hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, substituted or not) Represents an optionally substituted cycloalkyl or an optionally substituted acyl).
Or may together form a carbocycle or a heterocycle, and R ³ and R ⁵ are each independently hydrogen, halogen, optionally substituted alkyl, or optionally substituted alkenyl. , Optionally substituted alkynyl, optionally substituted phenyl, optionally substituted cycloalkyl, S (O) mR ¹⁴ (in the formula, R ¹⁴ is optionally substituted alkyl, substituted Optionally alkenyl, optionally substituted alkynyl, optionally substituted phenyl, optionally substituted cycloalkyl,
m represents 0, 1 or 2. ), NR ¹⁵ R ¹⁶ (wherein R
¹⁵ and R ¹⁶ are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl,
It may represent optionally substituted alkynyl, optionally substituted phenyl, optionally substituted cycloalkyl or may together form a ring. ), OR
¹⁷ (in the formula, R ¹⁷ is hydrogen, alkyl which may be substituted, alkenyl which may be substituted, alkynyl which may be substituted, phenyl which may be substituted, cycloalkyl which may be substituted) , Cyano, COOR ¹⁸ (in the formula, R ¹⁸ is hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, Represents an optionally substituted cycloalkyl), CONR ¹⁹ R ²⁰ (wherein R ¹⁹ and R ²⁰ are each independently hydrogen, an optionally substituted alkyl, an optionally substituted alkenyl, Represents an optionally substituted alkynyl, an optionally substituted phenyl, an optionally substituted cycloalkyl), PZ (OR ²¹ ).
(OR ²² ) (in the formula, Z represents O or S, R ²¹ and R ²² represent the same or differently substituted alkyl or optionally substituted phenyl), and R ⁴ is hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, optionally substituted cycloalkyl, COOR ²³ (formula Wherein R ²³ represents hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, or optionally substituted cycloalkyl. ), COR ²⁴ (wherein R ²⁴ is hydrogen, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted fluorine, Phenyl, which represents an optionally substituted cycloalkyl), CONR ²⁵ R ²⁶ (in the formula,
R ²⁵ and R ²⁶ are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, or optionally substituted. Represents a good cycloalkyl. ), S (O) _p R ²⁷ (wherein R ²⁷ is hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, Represents cycloalkyl which may be substituted, p represents 0, 1 or 2), and R ⁶ and R ⁷ are each independently hydrogen, halogen, optionally substituted alkyl or substituted. Optionally alkenyl, optionally substituted alkynyl, optionally substituted phenyl, optionally substituted cycloalkyl, S (O) qR ²⁸ (wherein R ²⁸ is optionally substituted alkyl). , Optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, optionally substituted cycloalkyl, q
Represents 0, 1 or 2. ), OR ²⁹ (wherein R ²⁹ is hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, optionally substituted Represents a good cycloalkyl), COOR ³⁰ (wherein R ³⁰ is hydrogen, an alkyl which may be substituted, an alkenyl which may be substituted, an alkynyl which may be substituted, or a phenyl which may be substituted). , Represents an optionally substituted cycloalkyl), CONR ³¹ R ³² (in the formula,
R ³¹ and R ³² are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, or optionally substituted. Represents a good cycloalkyl. ), A mono- or di-substituted amino group, and nitro, and R ⁸ are the same or different and are hydrogen, halogen, optionally substituted alkyl, optionally substituted alkenyl, or substituted. Optionally alkynyl, optionally substituted phenyl, optionally substituted cycloalkyl, S (O) rR ³³ (in the formula, R ³³ is optionally substituted alkyl, optionally substituted alkenyl. Represents optionally substituted alkynyl, optionally substituted phenyl, optionally substituted cycloalkyl, r
Represents 0, 1 or 2. ), OR ³⁴ (in the formula, R ³⁴ is hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, optionally substituted Represents a good cycloalkyl), COOR ³⁵ (in the formula, R ³⁵ is hydrogen, alkyl which may be substituted, alkenyl which may be substituted, alkynyl which may be substituted, or phenyl which may be substituted). , Represents an optionally substituted cycloalkyl), CONR ³⁶ R ³⁷ (in the formula,
R ³⁶ and R ³⁷ are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, or optionally substituted. Represents a good cycloalkyl. ), An amino group which may be mono- or di-substituted, nitro, cyano, and n represents 0, 1, 2 or 3. ] The pyrimidine derivative represented by these. 2. A compound represented by the general formula (I): [In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ ,
R ⁸ and n have the same meanings as described above. ] The herbicide which contains 1 type, or 2 or more types of the pyrimidine derivative represented by these as an active ingredient. 3. A compound represented by the general formula (I): [In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ ,
R ⁸ and n have the same meanings as described above. ] The agricultural or horticultural fungicide containing one or more types of the pyrimidine derivative represented by these as an active ingredient.