JPH0748359A - Fused pyrimidine derivatives, herbicides and agricultural / horticultural fungicides - Google Patents

Abstract

(57) [Summary] (Modified) [Structure] A pyrimidine derivative represented by the formula [I] or a salt thereof, and a herbicide and an agricultural / horticultural fungicide containing the compound as an active ingredient. [Wherein R ¹ and R ² are hydrogen, alkyl, phenyl, OR
⁵ , SR ⁶ , OCOR ⁷ , amino, Z ¹ P (= Z ² )
(Z ³ R ⁸ ) (Z ⁴ R ⁹ ), or together oxo, thioxo, cyclic ketal, = NOR ^15, etc., or —CH ₂ —O—, —O— (CH ₂ ) ₂ —N—, -S-
_{(CH 2) 2 -N -,} - N- (CH 2) represents _2-N-like, R ³ represents hydrogen, halogen, alkyl, nitro, cyano or the like, n represents 0, 1, 2, 3, Represents 4 or 5, R
⁴ represents hydrogen, halogen, alkyl, phenyl, cycloalkyl, nitro, cyano, etc., and A forms a 5- to 7-membered carbocycle or heterocycle. [Effect] It has excellent herbicidal activity and agricultural / horticultural bactericidal activity.

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. Am.
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 5] [In the formula, R ¹ and R ² are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, cyano, Optionally substituted alkoxycarbonyl, halogen, OR ⁵ (in the formula, R ⁵ is hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted Represents phenyl, optionally substituted cycloalkyl), SR ⁶ (in the formula, R ⁶ is hydrogen,
Represents an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted phenyl, and an optionally substituted cycloalkyl. ), OCOR ⁷ (wherein R ⁷ is hydrogen,
Represents an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted phenyl, and an optionally substituted cycloalkyl. ), Optionally substituted amino, Z
¹ P (= Z ² ) (Z ³ R ⁸ ) (Z ⁴ R ⁹ ) (wherein
R ⁸ and R ⁹ are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, or optionally substituted. Represents cycloalkyl,
Z ¹ , Z ² , Z ³ , and Z ⁴ each independently represent O or S. ), Or together, oxo, thioxo,
Cyclic ketal, cyclic Chioketa - le, = CR ¹⁰ R ¹¹ (wherein, R ^10, R ¹¹ are each independently hydrogen, nitro, cyano, alkyl optionally substituted, alkenyl which may be substituted, An optionally substituted alkynyl,
Optionally substituted alkylcarbonyl, optionally substituted carbamoyl, carboxy, optionally substituted alkyloxycarbonyl, optionally substituted alkenyloxycarbonyl, optionally substituted alkynyloxycarbonyl, substituted Optionally represents phenyl, optionally substituted alkylsulfonyl or optionally substituted phenylsulfonyl. ), = N
R ¹² (in the formula, R ¹² is hydrogen, alkyl which may be substituted, alkenyl which may be substituted, alkynyl which may be substituted, phenyl which may be substituted, and cyclo which may be substituted). Represents alkyl), = NN
R ¹³ R ¹⁴ (In the formula, R ¹³ and R ¹⁴ are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, or optionally substituted. Good phenyl, optionally substituted cycloalkyl, optionally substituted alkoxycarbonyl, represents carboxy), = NOR ¹⁵ (in the formula, R ¹⁵
Represents hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, or optionally substituted cycloalkyl. ),

[Chemical 6] Represents a spiro ring selected from, R ^{3 s} are the same or different, and are hydrogen, halogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, or optionally substituted. Good phenyl, optionally substituted cycloalkyl, S (O) pR
¹⁶ (wherein R ¹⁶ is an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted phenyl, an optionally substituted cycloalkyl, a substituted Represents an optionally substituted amino, p represents 0, 1 or 2), OR ¹⁷ (wherein, R ¹⁷ is hydrogen, optionally substituted alkyl, optionally substituted alkenyl, substituted Optionally alkynyl, optionally substituted phenyl, optionally substituted cycloalkyl, optionally substituted acyl, optionally substituted carbamoyl), C
OOR ¹⁸ (in the formula, R ¹⁸ is hydrogen, alkyl which may be substituted, alkenyl which may be substituted, alkynyl which may be substituted, phenyl which may be substituted, and cyclo which may be substituted). Represents alkyl),
CONR ¹⁹ R ²⁰ (In the formula, R ¹⁹ and R ²⁰ are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, or optionally substituted. Good phenyl, optionally substituted cycloalkyl, and NR ²¹ R ²² (in the formula, R
²¹ and R ²² are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl,
Represents alkynyl which may be substituted, phenyl which may be substituted, cycloalkyl which may be substituted, acyl which may be substituted and carbamoyl which may be substituted. ), Nitro, cyano, or two R
³ may form an optionally substituted 5 to 7 membered carbocycle or an optionally substituted 5 to 7 membered heterocycle. n represents 0, 1, 2, 3, 4 or 5, and R
⁴ is hydrogen, halogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, optionally substituted cycloalkyl, S ( O) qR
²³ (In the formula, R ²³ is hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, optionally substituted cycloalkyl , Represents an optionally substituted amino, and q represents 0, 1 or 2.), N
R ²⁴ R ²⁵ (in the formula, R ²⁴ and R ²⁵ are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl,
Represents phenyl which may be substituted, cycloalkyl which may be substituted, acyl which may be substituted and carbamoyl which may be substituted. ), OR ²⁶ (wherein R ²⁶ is hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, optionally substituted) Good cycloalkyl, optionally substituted acyl, optionally substituted carbamoyl)), C
OOR ²⁷ (wherein, R ²⁷ is hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, optionally substituted cyclo) Represents alkyl),
CONR ²⁸ R ²⁹ (In the formula, R ²⁸ and R ²⁹ are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, or optionally substituted. Good phenyl, optionally substituted cycloalkyl), nitro, cyano, A forms a 5- to 7-membered carbocycle or heterocycle,
Halogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, optionally substituted cycloalkyl, S (O) rR ³⁰ ( In the formula, R ³⁰ 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 30 Represents 0, 1 or 2.), NR 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 Represents optionally substituted cycloalkyl, optionally substituted acyl, optionally substituted carbamoyl), OR ³³ (in the formula,
R ³³ is hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, optionally substituted cycloalkyl, optionally substituted Good acyl,
It represents carbamoyl which may be substituted. ), COR
³⁴ (In the formula, R ³⁴ 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) , COO
R ³⁵ (wherein R ³⁵ is hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, or optionally substituted cyclo. Represents alkyl), CON
R ³⁶ R ³⁷ (In the formula, R ³⁶ and R ³⁷ are each independently hydrogen, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, or an optionally substituted Good phenyl, optionally substituted cycloalkyl), oxo, thioxo and cyano groups may be substituted. ] The pyrimidine derivative represented by this, a herbicide, and an agricultural and horticultural fungicide.

In the compound of the present invention, examples of the respective substituents include the substituents shown below. 1. Alkyl, alkenyl, alkynyl: halogen, hydroxy, alkoxy, phenyl, nitro, cyano, alkoxycarbonyl, alkylthio, alkylcarbonyloxy. Phenyl: halogen, alkyl, alkoxy, nitro 3. Cycloalkyl: alkyl, alkoxy, carboxy, alkoxycarbonyl 4. Amino: alkyl, alkenyl, alkynyl, alkoxycarbonyl, alkylcarbonyl 5. Carboxy alkali metal 6. Carbamoylalkyl In addition to the above as a substituent of alkyl in R ¹² , P (=
O) (OH) ₂ , P (= O) (O-alkyl) ₂ , P
(= S) (O-alkyl) ₂ , and examples of the substituent of alkynyl in R ⁴ include trialkylsilyl in addition to the above. In the present invention, the number of carbon atoms of alkyl is usually 1 to 6, the number of carbon atoms of alkenyl and alkynyl is 2 to 6, and the number of carbon atoms of cycloalkyl is 3 to 6.

The compound represented by the general formula [I] may be optical isomers such as when R ¹ and R ² are different, and these isomers are also included in the compound of the present invention.

The compound of the present invention can be produced by appropriately selecting the method shown below or a similar reaction known thereto.

[0008]

[Chemical 7]

[0009]

[Chemical 8]

[0010]

[Chemical 9]

[0011]

[Chemical 10]

[0012]

[Chemical 11]

[0013]

[Chemical 12]

[0014]

[Chemical 13]

[0015]

[Chemical 14]

[0016]

[Chemical 15]

[Wherein R ³ , R ⁴ , R ⁵ , R ⁶ , A, n
Represents the same meaning as described above, and R ′ ⁴ is hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, substituted Optionally represents cycloalkyl, R ″ ⁴ is S (O) qR ²³ (in the formula, R ²³ , q
Represents the same meaning as described above. ), NR ²⁴ R ²⁵ (wherein R ²⁴
And R ²⁵ has the same meaning as described above. ), OR ²⁶ (in the formula, R ²⁶ has the same meaning as described above), COOR ²⁷ (in the formula, R ²⁷ has the same meaning as described above), CONR ²⁸ R ²⁹
(In the formula, R ²⁸ and R ²⁹ have the same meanings as described above), nitro and cyano, R ³⁸ and R ′ ³⁸ represent alkyl,
R ³⁹ is S (O) rR ³⁰ (in the formula, R ³⁰ and r have the same meanings as described above), NR ³¹ R ³² (in the formula, R ³¹ and R
³² has the same meaning as described above. ), OR ³³ (wherein R ³³
Represents the same meaning as described above. ), Cyano, and R ⁴⁰ is
Represents an optionally substituted alkyl, an optionally substituted alkenyl, or an optionally substituted alkynyl,
X represents halogen, Y represents O, S, NR ⁴¹ (in the formula,
R ⁴¹ represents hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, or optionally substituted cycloalkyl. ), B is C ₂ -C ₄ alkylene which may be substituted and may have 1 or 2 unsaturated bonds, and V is
One of the carbons is O, S, NR ⁴² (wherein R ⁴² represents hydrogen, optionally substituted alkyl, optionally substituted phenyl, or optionally substituted cycloalkyl), and COR. ³⁴ (wherein, R ³⁴ is hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, optionally substituted 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 represents phenyl, optionally substituted cycloalkyl, and C ₁ to C ₃ alkylene which may be substituted by
Represents a leaving group such as halogen, alkylsulfonyl and benzylsulfonyl. ]

The reaction a) is carried out by reacting the raw material amidine or its organic acid salt such as mineral acid or carboxylic acid with the β-dicarbonyl compound in a solvent at room temperature to the boiling point of the solvent for 1 to 48 hours. By doing. As the solvent, alcohols such as ethanol, ethers such as THF, hydrocarbons such as benzene and toluene, DM
F and the like, or a mixture thereof and the like can be mentioned. Examples of the base include metal alcoholates of lower alcohols such as sodium methylate and potassium ethylate, potassium carbonate,
Inorganic bases such as sodium hydroxide, organic bases such as DBU and the like can be mentioned.

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. As the solvent, water, ethers such as dioxane, hydrocarbons such as benzene and toluene, halogenated hydrocarbons such as acetic acid, acetic anhydride, pyridine and methylene chloride, or a mixed homogeneous solvent or a mixed two-layer system thereof. Solvents may be mentioned. As the oxidant, KMnO ₄ , K ₂ Cr ₂ O ₇ ,
SeO _{2 and the} like can be mentioned.

The above-mentioned 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. As the halogenating agent, POX ₃ , PX ₃ , PCl ₅
(In the formula, X represents halogen.) And the like.

The above reaction d is carried out in the presence of an acid or a base at room temperature to the boiling point of the solvent for 1 to 48 hours. When Y = O, the solvent is
Examples thereof include water, dioxane and the like, or a mixture thereof. The acid used is sulfuric acid, sodium dihydrogen phosphate, a mixture of sodium dihydrogen phosphate and phosphoric acid, or the like.
The reaction is carried out at 0 ° C to the boiling point of the solvent for 1 to 10 hours. When Y = S, an error such as dioxane
Tellurium, hydrocarbons such as benzene, DMF and the like can be mentioned. As the base, sodium sulfide or the like is used, and the reaction is carried out at room temperature to the boiling point of the solvent for 1 to 48 hours. In the case of Y = NR ⁴¹ , examples of the solvent include water, alcohols such as methanol, ethers such as dioxane, DMF and the like, or a mixture thereof.
As a base, potassium carbonate, sodium hydroxide and the like can be used if necessary together with NH ₂ R ⁴¹ , and the reaction is carried out at room temperature to the boiling point of the solvent, if necessary under pressure for 1 to 48 hours.

The reaction (e) is carried out in a solvent in the presence of a base at room temperature to the boiling point of the solvent for a few minutes to 24 hours. Examples of the solvent include alcohols such as ethanol, 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 metal alcohols of lower alcohol such as sodium methylate and potassium ethylate, inorganic bases such as potassium carbonate and sodium hydroxide, organic bases such as DBU and the like.

The reaction of the above-mentioned f is carried out in the presence of a base in a solvent,
The reaction is carried out at 78 ° C to the boiling point of the solvent for a few minutes to 24 hours. The solvent may be an ether such as THF.
Tellurium, DMF, and the like. As the base, sodium hydride, potassium tert-butoxide, n
-Butyl lithium, lithium diisopropylamide and the like.

The reaction of the above-mentioned g is carried out by reacting in a halogenated hydrocarbon such as chloroform in the presence of a peracid such as m-chloroperbenzoic acid at -10 ° C to the boiling point of the solvent for 1 to 24 hours. To do. Alternatively, TH as a solvent
In the presence of oxygen using an ether such as F, DMF, etc., 0 °
Or react at the boiling point of C to the solvent for 1 to 48 hours,
Alternatively, it is carried out by air oxidation in a mixed two-layer system solvent of hydrocarbons such as toluene and water in the presence of a quaternary ammonium salt using an inorganic base such as sodium hydroxide.

The above reaction (h) is carried out by reacting in a solvent in the presence of a halogenating agent at -10 ° C to the boiling point of the solvent for 1 to 48 hours. Examples of the solvent include halogen hydrocarbons such as carbon tetrachloride and chloroform, hydrocarbons such as benzene and toluene, and a mixture thereof. Examples of the halogenating agent include N-chlorosuccinimide, N-bromosuccinimide and the like, and if necessary, light, benzoyl peroxide and the like can be used as a catalyst.

The above reaction i is carried out in a solvent in the presence of an oxidizing agent,
The reaction is carried out at 0 ° C to the boiling point of the solvent for 1 to 48 hours. Examples of the solvent include water, ethers such as dioxane, hydrocarbons such as benzene and toluene, halogenated hydrocarbons such as methylene chloride, and mixed homogeneous solvents or mixed bilayer solvents thereof. As the oxidizer, KMnO ₄ , K ₂ Cr ₂ O ₇ , NiO ₂ ,
Examples include chloranil, N-chlorosuccinimide, N-bromosuccinimide and the like.

The reaction of the above j is carried out using Law in a solvent such as ethers such as dimethoxyethane and hydrocarbons such as toluene.
The reaction is carried out in the presence of the Esson reagent at 0 ° C to the boiling point of the solvent for 1 to 24 hours.

The above reaction k is carried out by reacting in water, alcohols such as methanol or the like, or a mixture thereof in the presence of NaBH ₄ at 0 ° C. or the boiling point of the solvent for 1 to 48 hours. .

The above-mentioned reaction of l is carried out in a solvent in the presence of a base at 0
The reaction is carried out at a temperature of ° C to the boiling point of the solvent for a few minutes to 24 hours. As the solvent, alcohols such as ethanol, ketones such as acetone, ethers such as THF and dioxane, hydrocarbons such as benzene and toluene,
Examples thereof include DMF and the like, or a mixture thereof. As the base, sodium hydride, potassium ter
Examples thereof include inorganic bases such as t-butoxide, potassium carbonate and sodium hydroxide, and organic bases such as DBU.

The above reaction of m is carried out by reacting at 0 ° C. to the boiling point of the solvent in the absence of solvent or in the presence of a halogenating agent. As the solvent, water, methylene chloride,
Examples thereof include halogenated hydrocarbons such as chloroform, hydrocarbons such as benzene and toluene, and mixtures thereof. HX, PX ₃ , SOC as halogenating agent
l ₂ (wherein X represents halogen) and the like.

The above reaction o is carried out by reacting in a solvent at -78 ° C to the boiling point of the solvent for several minutes to 10 hours. Examples of the solvent include ethers such as diethyl ether, and examples of the alkylating agent include alkyl metals such as alkyl lithium and Grignard reagents such as alkyl magnesium bromide.

The above reaction of p is carried out by reacting in a solvent in the presence or absence of an acidic catalyst at 0 ° C. to the boiling point of the solvent. Examples of the solvent include alcohols such as ethanol, hydrocarbons such as toluene, halogenated hydrocarbons such as chloroform, ethers, DMF and the like, or a mixture thereof. Examples of the catalyst include inorganic acids such as hydrochloric acid and sulfuric acid, and organic acids such as acetic acid.

The reaction of the above q is carried out by reacting in a solvent in the presence or absence of a base at -78 ° C to the boiling point of the solvent. In addition, a catalyst may be added if necessary. As the solvent, ethers such as THF, benzene,
Hydrocarbons such as toluene, halogenated hydrocarbons such as chloroform and methylene chloride, and the like, or a mixture thereof can be used. Examples of the base include inorganic bases such as sodium hydride and potassium tert-butoxide, organic metal bases such as butyl lithium, and organic bases such as DBU and pyridine. As the catalyst, TiCl ₄ , SnCl ₄
Lewis acids such as.

The above reaction of r is carried out by a conventional method. (For example, J. Org. Chem., 27 , 998 (196
1))

In the above i) and ii)

[Chemical 16] The compounds are known or can be synthesized by a conventional method. (J. Org. Chem., 43 , 346 (197).
8) or J. Med. chem. , 28 , 934
(1985))

[0036]

EXAMPLES-Compounds The present invention will be further described with reference to Examples. The structure of the compound was determined by IR, NMR, MS and the like.

Example 1 2- (2-chlorobenzoyl) -4-trifluoromethyl-5,6-dihydrofuro [2,3-d] pyrimidine (Compound No. 13)

[0038]

[Chemical 17]

0.7 g of metallic sodium was dissolved in 50 ml of ethanol, and at room temperature, 5 g of 2- (2-chlorophenyl) acetamidine-hydrochloride and 5.3 g of α were dissolved.
-Trifluoroacetyl-γ-butyrolactone was added,
Stirring and heating under reflux were continued for 18 hours. The reaction solution was concentrated under reduced pressure, acidified with 10% hydrochloric acid, and the precipitated crystals were filtered off,
It was washed with water, washed with ether and dried to obtain 5.2 g of 2- (2-chlorobenzyl) -4-trifluoromethyl-5- (2-hydroxyethyl) -6-hydroxypyrimidine. 50 ml of dioxane and 10 ml of water,
3.4 g of SeO ₂ was added, and stirring and heating under reflux were continued for 3 days. Se was filtered off from the reaction solution, the filtrate was washed with saturated brine, dried over MgSO ₄ and concentrated under reduced pressure, and the precipitated crystals were washed with ether to give 2- (2-chlorobenzoyl)-.
4 g of 4-trifluoromethyl-5- (2-hydroxyethyl) -6-hydroxypyrimidine was obtained. Then add 200 ml of toluene and 2 g of POCl ₃ to this,
After stirring and heating under reflux for 2 hours, the reaction solution was concentrated, water was added, the mixture was extracted with methylene chloride, washed with saturated brine, and washed with Mg.
After drying with SO ₄ , the mixture was concentrated under reduced pressure and the obtained crystals were purified with ether to give the title compound (3 g).

Example 2 2- (2-chlorobenzoyl) -4-trifluoromethyl-furo [2,3-d] pyrimidine (Compound No. 16)

[0041]

[Chemical 18]

0.5 g of 2- (2-chlorobenzoyl)
-4-Trifluoromethyl-5,6-dihydrofuro [2,3-d] pyrimidine was dissolved in 20 ml of toluene, 2 g of NiO ₂ was added, and the mixture was heated under reflux for 5 hours. The insoluble material was filtered off from the reaction solution, the filtrate was washed with saturated brine, dried over MgSO ₄ , concentrated under reduced pressure and purified by silica gel column chromatography to give the title compound (25%).
0 mg was obtained.

Example 3 2- (2-chlorobenzoyl) -4-trifluoromethyl-5,6-dihydropyrrolo [2,3-d] pyrimidine (Compound No. 17)

[0044]

[Chemical 19]

5 g of 2- (2-chlorobenzoyl) -4
-Trifluoromethyl-5- (2-hydroxyethyl)
-6-hydroxypyrimidine were dissolved in POCl ₃ in 30 ml, it was heated under reflux for 2 hours. The reaction solution is concentrated under reduced pressure,
Pour into water, extract with methylene chloride, wash with saturated saline,
Dry over MgSO ₄ , concentrate under reduced pressure and purify by silica gel column chromatography to give 2- (2-chlorobenzoyl) -4-trifluoromethyl-5- (2-chloroethyl) -6-chloropyrimidine (3.0 g). Obtained. 1 g of 2- (2-chlorobenzoyl) -4-trifluoromethyl-5- (2-chloroethyl) -6-chloropyrimidine was dissolved in 10 ml of MeOH, 3 ml of aqueous ammonia was added thereto, and the tube was sealed, 100 Stir at 18 ° C. for 18 hours. Ethyl acetate was added to the reaction solution, washed with saturated saline solution, and MgS
The extract was dried over O ₄ , concentrated under reduced pressure, and purified by silica gel column chromatography to obtain 300 mg of the title compound.

Example 4 2- (2-chlorobenzyl) -4-hydroxy-5,
6,7,8-Tetrahydroquinazoline (Compound No. 1)

[0047]

[Chemical 20]

0.95 g of metallic sodium was dissolved in 50 ml of ethanol, to which 7 g of 2- (2-chlorophenylacetamidine-hydrochloride) and 6.3 g of 2-ethoxycarbonylcyclohexanone were added and heated for 18 hours. After refluxing, the reaction mixture was concentrated, acidified with 10% hydrochloric acid, and the precipitated crystals were washed with water and ether and dried to give 2- (2-chlorobenzyl) -4-hydroxy-.
7.2 g of 5,6,7,8-tetrahydroquinazoline was obtained.

Example 5 2- (2-chlorobenzoyl) -4-chloro-5,6,
7,8-Tetrahydroquinazoline (Compound No. 3)

[0050]

[Chemical 21]

6 g of 2- (2-chlorobenzyl) -4-
Hydroxy-5,6,7,8-tetrahydroquinazoline in 60 ml dioxane, 12 ml water and 3 g SeO 2.
₂ was added and the mixture was heated under reflux for 18 hours. The reaction solution was concentrated under reduced pressure, 20 ml of POCl ₃ was added thereto, and the mixture was heated under reflux for 3 hours. Se was separated from the reaction solution by filtration, the filtrate was concentrated under reduced pressure, water was added, the mixture was extracted with ethyl acetate, washed with saturated brine, dried and concentrated under reduced pressure, and purified by silica gel column chromatography. 4.2 g of (2-chlorobenzoyl) -4-chloro-5,6,7,8-tetrahydroquinazoline was obtained.

Example 6 2- (2-chlorobenzoyl) -4-methoxy-5
6,7,8-Tetrahydroquinazoline (Compound No. 4)

[0053]

[Chemical formula 22]

0.7 g of 2- (2-chlorobenzoyl)
-4-Chloro-5,6,7,8-tetrahydroquinazoline was dissolved in 10 ml of methanol, 0.6 ml of a sodium methylate methanol solution (28%) was added, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into water, extracted with ethyl acetate, washed with saturated brine, dried over MgSO ₄ , and concentrated under reduced pressure to give the title compound (0.7 g).

Example 7 2- (2-chlorobenzyl) -4-hydroxyquinazoline (Compound No. 6)

[0056]

[Chemical formula 23]

0.6 g of metallic sodium was dissolved in 50 ml of ethanol and at room temperature 5 g of ethyl 2- (2-chlorophenyl) -acetimidate-hydrochloride was added to 3.9.
Ethyl 2-aminobenzoate (g) was added, and stirring and heating under reflux were continued for 18 hours. The reaction solution was concentrated under reduced pressure, acidified with 10% hydrochloric acid, and the precipitated crystals were separated by filtration, washed with water and ether, and dried to obtain 4 g of 2- (2-chlorobenzyl) -4-hydroxyquinazoline.

Example 8 2- (2-chlorobenzoyl) -4-hydroxyquinazoline (Compound No. 7)

[0059]

[Chemical formula 24]

1.2 g of 2- (2-chlorobenzyl)-
4-hydroxyquinazoline and 20 ml dioxane 4
A mixture of ml of water and 1.0 g of SeO ₂ was heated under reflux for 18 hours. Se was filtered off from the reaction solution, the filtrate was washed with saturated brine, dried over MgSO ₄ , concentrated under reduced pressure, and the precipitated crystals were washed with ether, and 2- (2-chlorobenzoyl) -4-hydroxy was added. 1.0 g of quinazoline was obtained.

Example 9 2- (2-benzoyl) -4-methylthioquinazoline (Compound No. 9)

[0062]

[Chemical 25]

2- (2-chlorobenzoyl) -4-hydroxyquinazoline 1.0 g, 20 ml toluene and 2 g
POCl ₃ was added and the mixture was heated under reflux for 2 hours. The reaction solution was concentrated under reduced pressure, and 10 ml of dioxane and 4 ml of a methyl mercaptan sodium aqueous solution (15%) were added thereto,
Stir at room temperature for 2 hours. The reaction mixture was poured into water, extracted with ethyl acetate, washed with saturated brine, dried over MgSO ₄ , concentrated under reduced pressure, and the precipitated crystals were washed with ether to give the title compound (0.7 g). .

Example 10 2- (2-Chloro-6-fluorobenzyl) -4-trifluoromethyl-dihydropyrano [4,3d] pyrimidine

[0065]

[Chemical formula 26]

0.16 g of sodium metal was dissolved in 20 ml of ethanol, to which 1.9 g of 2- (2-chloro-6-fluorophenyl) acetamidine-hydrochloride and 1.0 g of 3-trifluoro were added. Acetyl-4-tetrahydropyranone was added, and stirring and heating under reflux were continued for 3 hours. The reaction solution was concentrated under reduced pressure, acidified with 10% hydrochloric acid,
The mixture was extracted with ethyl acetate, dried over magnesium sulfate, and concentrated under reduced pressure. This was purified by silica gel column chromatography to obtain 0.6 g of the title compound.

Example 11 Ethyl-3- (2-chlorophenyl) -3- (4-trifluoromethyl-5,6dihydrofuro [2,3d] pyrimidin-2-yl) propeneate

[0068]

[Chemical 27]

1.0 g of 2- (2-chlorobenzoyl)
-4-trifluoromethyl-5,6 dihydrofuro [2,
3d] Pyrimidine and 1.06 g of triphenylcarbetoxymethylenephosphorane were dissolved in 15 ml of benzene, and stirring and heating under reflux were continued for 24 hours. The reaction solution was concentrated under reduced pressure and purified by silica gel column chromatography,
0.78 g of the title compound was obtained.

Representative examples of the compounds of the present invention, including the compounds of the above Examples, are shown in Table 1.

[0071]

[Table 101]

[0072]

[Table 102]

[0073]

[Table 103]

[0074]

[Table 104]

[0075]

[Table 105]

[0076]

[Table 106]

[0077]

[Table 107]

[0078]

[Table 108]

[0079]

[Table 109]

[0080]

[Table 110]

[0081]

[Table 111]

[0082]

[Table 112]

[0083]

[Table 113]

[0084]

[Table 114]

[0085]

[Table 115]

[0086]

[Table 116]

[0087]

[Table 117]

[0088]

[Table 118]

[0089]

[Table 119]

[0090]

[Table 120]

[0091]

[Table 121]

[0092]

[Table 122]

[0093]

[Table 123]

[0094]

[Table 124]

[0095]

[Table 125]

[0096]

[Table 126]

[0097]

[Table 127]

[0098]

[Table 128]

[0099]

[Table 129]

[0100]

[Table 130]

[0101]

[Table 131]

[0102]

[Table 132]

[0103]

[Table 133]

[0104]

[Table 134]

[0105]

[Table 135]

[0106]

[Table 136]

[0107]

[Table 137]

[0108]

[Table 138]

[0109]

[Table 139]

[0110]

[Table 140]

[0111]

[Table 141]

[0112]

[Table 142]

[0113]

[Table 143]

[0114]

[Table 144]

[0115]

[Table 145]

[0116]

[Table 146]

[0117]

[Table 147]

[0118]

[Table 148]

[0119]

[Table 149]

[0120]

[Table 150]

[0121]

[Table 151]

[0122]

[Table 152]

[0123]

[Table 153]

[0124]

[Table 154]

[0125]

[Table 155]

[0126]

[Table 156]

[0127]

[Table 157]

[0128]

[Table 158]

[0129]

[Table 159]

[0130]

[Table 160]

[0131]

[Table 161]

[0132]

[Table 162]

[0133]

[Table 163]

[0134]

[Table 164]

[0135]

[Table 165]

[0136]

[Table 166]

[0137]

[Table 167]

[0138]

[Table 168]

[0139]

[Table 169]

[0140]

[Table 170]

[0141]

[Table 171]

[0142]

[Table 172]

[0143]

[Table 173]

[0144]

[Table 174]

[0145]

[Table 175]

[0146]

[Table 176]

[0147]

[Table 177]

[0148]

[Table 178]

[0149]

[Table 179]

[0150]

[Table 180]

[0151]

[Table 181]

[0152]

[Table 182]

[0153]

[Table 183]

[0154]

[Table 184]

[0155]

[Table 185]

[0156]

[Table 186]

[0157]

[Table 187]

[0158]

[Table 188]

[0159]

[Table 189]

[0160]

[Table 190]

[0161]

[Table 191]

[0162]

[Table 192]

[0163]

[Table 193]

The compound of the present invention shows 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 barnyard grass, corn, wheat,
It also contains compounds that show selectivity for crops such as soybeans. In addition, the compound of the present invention, Nobie of paddy weeds, Tamagayatsu,
It also contains compounds that have excellent herbicidal activity against weeds such as Japanese sardines and have 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
niamail ), 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
r a viticola) it can be used for the control of such.

[0166] Further, 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 is also used as a general antifungal agent at home and in industry. You can also do it.

[0167]

Means for Solving the Problems-Herbicide, fungicide When the compound of the present invention thus obtained is actually applied, 1 or 2 of the compounds represented by the above general formula [I] is used.
It contains the above as an active ingredient and has a form similar to that of a normal pesticide. That is, the active ingredient compound is generally used in the form of a wettable powder, an emulsion, a granule, a powder, an aqueous solvent, a flowable agent, etc. by mixing an appropriate amount with a carrier. When a solidifying agent is intended as an additive and a carrier, soybean powder, vegetable powder such as wheat flour, diatomaceous earth, burnt stone, gypsum, talc,
Mineral fine powders such as pyrophyllite, clay, white carbon (silica), bentonite, mineral oil and vegetable oil 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 weed germination 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.

[Insecticides / Acaricides] 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.

Examples-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, but can be varied within a wide range. Parts in the formulation examples indicate parts by weight.

Example 12 Wettable powder Compound of the present invention 40 parts Diatomaceous earth 53 parts Higher alcohol sulfate ester 4 parts Alkylnaphthalene sulfonate 3 parts If the above is uniformly mixed and finely ground, the active ingredient 40
% Of wettable powder is obtained.

Example 13 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 having 20% of an active ingredient.

Example 14 Emulsion Compound of the present invention 30 parts Xylene 33 parts Dimethylformamide 30 parts Polyoxyethylene alkylallyl ether 7 parts The above components are mixed and dissolved to obtain an emulsion containing 30% of the active ingredient.

Example 15 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 16 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 thereof is 0.5 to 1.
Granulate into 0 mm granules to obtain granules containing 5% of the active ingredient.

Example 17 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 components are well pulverized and mixed, and water is added and kneaded well.
Granulate and dry to obtain granules with 5% active ingredient.

Example 18 Dust Compound of the present invention 10 parts Talc 89 parts Polyoxyethylene alkylallyl ether 1 part The above ingredients are mixed evenly and finely ground to obtain the active ingredient 10
% Powder is obtained.

Example 19 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 are mixed until the particle size becomes 1 micron or less. Wet milling gives a suspension with 10% active ingredient.

[0183]

Next, test examples relating to the effects of the herbicide 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 liquid of the wettable powder shown in Example 13 was uniformly sprayed on the soil cover so that 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. The results are shown in Table 2.

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 Numerical values indicate intermediate values of 0 and 2, 2 and 4, 4 and 6, 6 and 8, and 8 and 10, respectively.

[0185]

[Table 201]

[0186]

[Table 202]

Test Example 2 Paddy Field Soil Treatment Test Paddy field soil was filled in a 150 cm ² pot, seeds of Novier, Pleurotus cornucopiae, and Pokeweed were sown, and rice at the two-leaf stage was transplanted. After irrigation to 3 cm on the next day, a prescribed amount of each compound granule was treated and grown in a greenhouse. Three weeks after the chemical treatment, the weeding effect of each weed was investigated according to the above criteria, and the results shown in Table 3 were obtained.

[0188]

[Table 301]

[0189]

[Table 302]

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 Cucumber beet and disease control test (prevention test) Cucumber grown in a greenhouse for about 3 weeks (quality: Sagamihanjiro)
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 4.

[0192]

[Table 401]

[0193]

[Table 402]

Test Example 4 Cucumber downy mildew control test (therapeutic test) [0194] This seedling ( Pseudoperonospora) collected from diseased leaves of cucumber downy mildew was applied to seedlings of a cucumber (cultivar Sagamihanjiro, 1,1 leaf stage) grown in a greenhouse. cubens
The suspension of zoosporangium of is ) was spray-inoculated and kept in an inoculation box at 25 ° C. and high humidity. 20 hours after the inoculation, a chemical solution of the wettable powder of the compound of the present invention having a predetermined concentration is sprayed, and after air-drying, 24-
It was transferred to a thermostatic chamber at 26 ° C. and a humidity of 70% or more, and the disease state was investigated 3 days later, and the control effect was obtained. The results are shown in Table 5.

[0195]

[Table 5]

Test Example 5 Grape downy mildew control test Leaves planted outdoors (variety "Kaiji", 3rd grade) were cut off 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 zoosporangia of grapevine and disease fungus ( Plasmopara viticola ) was sprayed and inoculated into the drug solution at a concentration, 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.

[0197]

[Table 601]

[0198]

[Table 602]

Test Example 6 Tomato epidemic 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 7.

[0200]

[Table 7]

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code Internal reference number FI Technical indication C07D 239/90 8615-4C 239/91 8615-4C 239/93 8615-4C 403/04 233 405 / 04 239 413/04 239 417/04 239 471/04 107 E 487/04 140 7019-4C 150 7019-4C 491/048 7019-4C 491/052 7019-4C 495/04 105 Z 111 C07F 9/6512 9155- 4H // (C07D 403/04 233: 00 239: 00) (C07D 405/04 239: 00 303: 00) (C07D 413/04 239: 00 263: 00) (C07D 417/04 239: 00 277: 00) ) (C07D 487/04 223: 00 239: 00) (C07D 491/048 239: 00 307: 00) (C07D 491/052 239: 00 309: 00) (C07D 495/04 239: 00 333: 00) ( C07D 495/04 239: 00 335: 00) (72) Inventor Hiroyuki Adachi 345 Yanagicho, Takada, Odawara, Kanagawa Japan Tatsu Co., Ltd. in the Odawara Research Institute (72) Inventor Shigeo Yamada 345 Yanagicho, Takada, Odawara, Kanagawa Japan Soda Co., Ltd. Inside the Odawara Research Institute (72) Inventor, Takashi 345 Yanagicho, Takada, Odawara, Kanagawa Japan Soda Co., Ltd. Inside the research institute (72) Inventor Susumu Shimoda 345 Yanagicho, Takada, Odawara, Kanagawa Nihon Soda Co., Ltd. Inside the Odawara Research Center (72) Inventor Akira Hashimoto 2-2-1 Otemachi, Chiyoda-ku Tokyo

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 phenyl, cyano, Optionally substituted alkoxycarbonyl, halogen, OR ⁵ (in the formula, R ⁵ is hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted Represents phenyl, optionally substituted cycloalkyl), SR ⁶ (in the formula, R ⁶ is hydrogen,
Represents an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted phenyl, and an optionally substituted cycloalkyl. ), OCOR ⁷ (wherein R ⁷ is hydrogen,
Represents an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted phenyl, and an optionally substituted cycloalkyl. ), Optionally substituted amino, Z
¹ P (= Z ² ) (Z ³ R ⁸ ) (Z ⁴ R ⁹ ) (wherein
R ⁸ and R ⁹ are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, or optionally substituted. Represents cycloalkyl,
Z ¹ , Z ² , Z ³ , and Z ⁴ each independently represent O or S. ), Or together, oxo, thioxo,
Cyclic ketal, cyclic thioketal, = CR ¹⁰ R ¹¹ (in the formula, R ¹⁰ and R ¹¹ are each independently hydrogen, nitro, cyano, optionally substituted alkyl, optionally substituted alkenyl, or substituted Alkynyl, which may be
Optionally substituted alkylcarbonyl, optionally substituted carbamoyl, carboxy, optionally substituted alkyloxycarbonyl, optionally substituted alkenyloxycarbonyl, optionally substituted alkynyloxycarbonyl, substituted Optionally represents phenyl, optionally substituted alkylsulfonyl or optionally substituted phenylsulfonyl. ), ═NR ¹² (wherein R ¹² is hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, or optionally substituted) Also represents cycloalkyl), ═NNR ¹³ R ¹⁴
(In the formula, R ¹³ and R ¹⁴ are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, substituted Optionally substituted cycloalkyl, optionally substituted alkoxycarbonyl, represents carboxy, = NOR ¹⁵ (wherein, R ¹⁵ is hydrogen, optionally substituted alkyl, optionally substituted alkenyl, Represents an optionally substituted alkynyl, an optionally substituted phenyl, or an optionally substituted cycloalkyl), and Represents a spiro ring selected from, R ³ is the same or different and is hydrogen, halogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, or optionally substituted. Good phenyl, optionally substituted cycloalkyl, S (O) pR ¹⁶ (wherein, R ¹⁶ is optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, substituted Phenyl which may be substituted, cycloalkyl which may be substituted, amino which may be substituted, p represents 0, 1 or 2), OR ¹⁷ (in the formula, R ¹⁷ is hydrogen or substituted) Optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, optionally substituted cycloalkenyl Le, acyl which may be substituted, represents a carbamoyl substituted.), COOR ¹⁸ (wherein, R ¹⁸ is hydrogen, alkyl optionally substituted, an optionally substituted alkenyl, substituted Optionally alkynyl, optionally substituted phenyl, optionally substituted cycloalkyl), CONR ¹⁹ R ²⁰ (in the formula, R ¹⁹ and R
²⁰ is independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, optionally substituted cycloalkyl Represent ),
NR ²¹ R ²² (in the formula, R ²¹ and R ²² are each independently hydrogen, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, or an optionally substituted Good phenyl, optionally substituted cycloalkyl, optionally substituted acyl, optionally substituted carbamoyl), nitro,
5 optionally substituted with cyano or two R ³
It may form a 7- to 7-membered carbocycle or an optionally substituted 5- to 7-membered heterocycle. n is 0, 1, 2, 3, 4
Or represents 5, R ⁴ is hydrogen, halogen, alkyl optionally substituted, alkenyl which may be substituted, alkynyl which may be substituted, phenyl which may be substituted, may be substituted Good cycloalkyl, S (O) qR
²³ (In the formula, R ²³ is hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, optionally substituted cycloalkyl , Represents an optionally substituted amino, and q represents 0, 1 or 2.), N
R ²⁴ R ²⁵ (in the formula, R ²⁴ and R ²⁵ are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl,
Represents phenyl which may be substituted, cycloalkyl which may be substituted, acyl which may be substituted and carbamoyl which may be substituted. ), OR ²⁶ (wherein R ²⁶ is hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, optionally substituted) Good cycloalkyl, optionally substituted acyl, optionally substituted carbamoyl)), C
OOR ²⁷ (wherein, R ²⁷ is hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, optionally substituted cyclo) Represents alkyl),
CONR ²⁸ R ²⁹ (In the formula, R ²⁸ and R ²⁹ are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, or optionally substituted. Good phenyl, optionally substituted cycloalkyl), nitro, cyano, A forms a 5- to 7-membered carbocycle or heterocycle, and halogen, optionally substituted alkyl, substituted Optionally alkenyl, optionally substituted alkynyl,
Optionally substituted phenyl, optionally substituted cycloalkyl, S (O) rR ³⁰ (wherein, R ³⁰ is optionally substituted alkyl, optionally substituted alkenyl, optionally substituted Represents an optionally substituted alkynyl, an optionally substituted phenyl, an optionally substituted cycloalkyl, and r represents 0, 1 or 2.), NR ³¹ R ³²
(In the formulae, R ³¹ and R ³² are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl, substituted Optionally substituted cycloalkyl, optionally substituted acyl, optionally substituted carbamoyl), OR ³³ (in the formula, R ³³ is hydrogen, optionally substituted alkyl, substituted) Optionally alkenyl, optionally substituted alkynyl,
Represents phenyl which may be substituted, cycloalkyl which may be substituted, acyl which may be substituted and carbamoyl which may be substituted. ), COR 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, substituted Represents an optionally substituted cycloalkyl), oxo, thioxo or cyano group. ] The pyrimidine derivative or its salt represented by these. 2. A compound represented by the general formula [I]: [In the formula, R ¹ , R ² , R ³ , R ⁴ , A 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 , A 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.