JPS608241A - Oxobutoxyphenyl derivative and fungicide - Google Patents

Abstract

NEW MATERIAL:The compound of formula I {R is H, R1CO- [R1 is (substituted) phenyl or heterocyclic group], R2SO2- (R2 is 1-5C alkyl, 2-4C alkenyl, etc.), group of formula II (R3 and R4 are H, 1-5C alkyl, 3-7C cycloalkyl, etc.) or group of formula III (R6 and R7 are H or 1-5C alkyl; X is O or S)}. EXAMPLE:p-(3,3-Dimethyl-2-oxobutoxy)phenylmethanesulfonate. USE:An agricultural and horticultural fungicide effective to the control of various blights of agricultural and horticultural plants, e.g. damping-off of cucumber, Fusarium yellow of radish, etc. PREPARATION:The compound of formula I can be prepared either by converting the OH of p-(3,3-dimethyl-2-oxobutoxy)phenol to alkali metal salt, and reacting with alkanesulfonyl chloride, or by reacting a phenolic compound with an alkanesulfonyl chloride in a solvent such as tetrahydrofuran in the presence of a base such as triethylamine.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a ginphenyl derivative and a fungicide containing the compound as an active ingredient.

[In the formula, R represents a hydrogen atom, R1Co;

represents a phenyl group, an optionally substituted phenyl group, a heterocyclic group, or R also represents R2S02-, R2 is C1
．． , 5 alkyl group, C2-4 alkenyl group, C3-7 cycloalkyl group, C1. , 4-halokene alkyl group, C
2. ,,4haloke9alkenyl group, C5-7 halokenecycloalkyl group, phenyl group, optionally substituted phenyl group, C1-5 alkylamino group, R5COMH%
In this formula, R5 represents a C,-5 alkyl group.

Or one or both are C1-5 alkyl groups,
C3-7 cycloalkyl M, C1-s halodane alkyl group, C5-7 haloke8 cycloalkyl group, phenyl group, and optionally substituted phenyl group.

R60, R represents P-, and R6, R, is a hydrogen atom R70
' Alternatively, one or both of them represents a C1-5 alkyl group, and X represents oxygen or sulfur. ] The compound of the present invention can be prepared by, for example, a method in which the hydroxyl group of p(3,3-nomethyl-2-oxobutoxy)phenol is converted into an alkali metal salt, and this is reacted with, for example, alkanesulfonyl chloride, or by an alternative method of the method. and alkanesulfonyl chloride r with sodium amide, potassium carbonate,
triethylamine, sodium hydroxide, barium oxide,
Silver oxide, hydride) a7thone, nonotyl sulfoxide, trimethylformamide,
It can be easily synthesized by a reaction method in a solvent such as tetrahydrofuran.

It can also be synthesized by a method in which the phenol compound is reacted with an isocyanate ester in a solvent such as ether, THF, benzene, carbon tetrachloride, etc. using a base such as triethylamine or hisricine as a catalyst. Of course, various other organic synthesis reactions can also be used.

Typical synthesis methods for the compounds of the present invention will be shown below and explained in more detail, but as mentioned above, the methods are not limited thereto.

Synthesis Example ■ p-(3,3-dimethyl-2-oxobutoxy)phenylmethanesulfonate p-(3,:3-nomethyl-2-oxobutoxy)phenol 1. 09 and triethylamine 5.69 to tetrahydrofuran 1. Methanesulfonyl chloride 7I is gradually added dropwise. After completion of the dropwise addition, the mixture was stirred at room temperature for 15 hours. After the reaction is stirred at 60° C. for 3 hours, the reaction solution is washed twice with thorium hydrogen carbonate solution, washed with water, and dried over thorium sulfate.

Thereafter, the solvent is distilled off to obtain an oily target product.

■p-(3,3-dimethyl-2-oxobutoxy)phenyl-m-toluenecarpoxylate-1・p-(3
．． 3-monomethyl-2-oxobutquine) phenol4.
Dissolve 2 g in gin and gradually add m-methylbennoyl chloride dropwise. Stir at room temperature for 6 hours. After the reaction is complete, pour the reaction solution into a large amount of water to obtain crystals. Recrystallize these crude crystals from ethanol. .

Compounds shown in Table (I) can be synthesized by similar operations.

The compounds of the present invention are effective in controlling a wide range of diseases of agricultural and horticultural crops, and the main ones include the following.

Paddy rice: Seedling blight, damping-off disease; Wheat: damping-off, sclerotium disease; Noyaga potato: dry rot, black bruising, white silk disease, sclerotia; Beans: damp-off disease, damping-off disease, sclerotia; Tobacco buckthorn disease, mai disease, white silk disease;
Sugar beet seedling damping-off.

Root rot, white silk disease; Konnyaku dry rot, white silk disease.

Root rot diseases; Tomato wilt, seedling damping-off, white silk disease; Eggplant half-wilt, brown rot, seedling damping-off, white silk disease.

Cucumber damping off late blight, seedling damping off, white silk disease, vine splitting disease,
Radish yellowing; Chinese cabbage sclerotium, root club; onion dry rot; lettuce hem blight; Ichiko 8 yellowing However, it can be used as it is or mixed with a carrier (diluent) to form powders, granules, wettable powders, emulsions, oils, and other suitable commonly used agents. In this case, if necessary, a spreading agent, an emulsifier, 7:
11 Spreading agents, fixing agents, etc. are used as appropriate, and they can also be used in combination or mixed with other types of fungicides, insecticides, herbicides, fertilizers, etc.

Example 1 Powder Compounds listed in the table 3 parts Clay 40 parts Talc 57 parts Example 2 Wettable powder Compounds listed in the table 75 parts Polyoxyethylene alkyl allyl ether 9 parts White carbon 16 parts There are no restrictions on the amount of spraying. However, when spraying on fields where crops are grown, the active ingredient compounds (A,
As for I), 50 to 10005'/10a, and when applied into soil, 1 to 10 kgA·cm/XOa is appropriate. Of course, this is just a guideline, and it may be adjusted as necessary, taking into account factors such as the type of crop, the type and degree of damage, the season, the weather, and the dosage form of the drug.

In order to specifically explain the effects of the compounds of the present invention, typical test examples will be shown below. However, these are merely examples, and it goes without saying that the application examples of the present invention are not limited to these.

Test Example-1 Efficacy test for cucumber seedling blight (Test method) Pythium aphanid
ermatum) in a diameter of 15 mm.
Pour into crn clay pot. After sowing 20 pre-germinated cucumber seeds (variety: Sumo Hanshiro) per pot on the surface, cover the soil with contaminated soil, and immediately apply an amount equivalent to 3 t/m2 of the chemical solution diluted to the specified concentration evenly over the surface. Irrigate. After pouring water, it was lightly watered and left in the greenhouse. During the test, the water was appropriately bent, and 14 days after treatment, the number of germinated plants and the number of lodging plants were examined, and the control value was calculated as follows.

However, the number of runs shall be three.

Test Example-2 Cucumber seedling damping-off efficacy test Test method> Cucumber seedling damping-off fungus (Rhizoctonia 5ol)
soil artificially contaminated with Ani 3A) with a diameter of 15 cm.
Pour into an M clay pot. After sowing 920 pre-germinated cucumber seeds (variety: Sumo Hanshiro) on the surface of the pot, cover the soil with contaminated soil, and immediately sprinkle the equivalent of 317 m2 of a chemical solution diluted to the specified concentration uniformly over the surface. do. After rinsing, the plants were lightly watered and left in a greenhouse. Water as needed during the test.
Fourteen days after the treatment, the number of germinated plants and lodging plants were examined, and the control value was calculated as follows.

However, the number of runs shall be three.

Test Example-3 Fusarium oxysporum efficacy test <Test method> Fusarium oxysporum
Soil artificially contaminated with F. raphani) was packed in a clay pot with a diameter of 15 Cn+. After sowing 10 pre-germinated radish seeds R (variety: j￥ Samemiyaju) per pot on the surface, cover with contaminated soil and immediately dilute to the specified concentration/equivalent to 3t/n, 2 of the chemical solution. Irrigate the amount evenly over the surface.

After pouring with water, the plants were lightly water-bent, left in a greenhouse, and watered appropriately.After 60 to 1 treatment, the degree of disease onset was investigated as follows.

However, the number of runs shall be 5.

Continuation of page 1 9Int, C1,' Identification symbol Internal organization - (:07
C143/86 6667 C07F 9/12 7327 9/18 7327 0 Inventor Hiroshi Kojima Showa Denko K.K. Biochemistry Laboratory, 2-24-25 Tamagawa, Ota-ku, Tokyo

Claims (2)

[Claims] (1) General formula [In the formula, R represents a hydrogen atom, R1C0, and R1 in the formula
represents a phenyl group, an optionally substituted phenyl group, or a heterocyclic group. In addition, R also represents R25O2-, and R2 is C
l-5 alkyl group, C2-4 alkenyl group, C3-7 cycloalkyl M, C1-4 halogenalkyl group, C2-
4-haloke8-alkenyl group, C3-7-haloke8-cycloalkyl group, phenyl group, optionally substituted phenyl group, C1-5 alkylamino group, R3C0NH- (fork group, C3-7 cycloalkyl group, ' indicates a C1-5 halogen alkyl group, a C3,,7 halogen cycloalkyl group, a phenyl group, or an optionally substituted phenyl group. One or both of the children represents a C4-5 alkyl group, and X is oxygen or sulfur.] An oxobutoxyphenyl derivative represented by: (2) [In the formula, R represents a hydrogen atom, R, Co, and in the formula, R1
represents a phenyl group, an optionally substituted phenyl group, or a heterocyclic group. In addition, R also represents R25O2-, and R2 is C
1,,5 alkyl group, C2-4 alkenyl group, C3-
7 cycloalkyl group, C1,,,4 halokene alkyl group, C2-4 halokene alkenyl a, C3-7 halogen cycloalkyl group, phenyl group, optionally substituted phenyl group, C1-5 alkylamino group ,R,coNn(
I)-, in which R3 represents a C4-5 alkyl group. Further, R represents R4-NC0-, R3 and R4 are hydrogen atoms, 5, or one or both are 01. ．． 5 alkyl &, C3-7 cycloalkyl group, C1-5 position 8
argyl group, C5-7 halokenecycloalkyl group,
Indicates a phenyl group and an optionally substituted phenyl group. One or both of the children represents a C1-5 alkyl group, and X represents oxygen or sulfur. ] An agricultural and horticultural fungicide containing an oxobutoxyphenyl derivative represented by the following as an active ingredient: