Phenyl urea compound, and use thereof

Abstract

A compound represented by formula (1) is described: ##STR00001##
The compound has an excellent efficacy for controlling plant diseases, and is thus useful as an active ingredient for an agent for controlling plant diseases.

Claims

1. A compound represented by formula (1): ##STR00004##

2. An agent for controlling a plant disease which comprises the compound according to claim 1.

3. A method for controlling a plant disease which comprises applying an effective amount of the compound according to claim 1 to a plant or soil for cultivating the plant.

Description

EXAMPLES

(1) Hereinafter, the present invention is explained in more detail by using Preparation example and Test example, however, the present invention should not be limited to these examples.

(2) First, the Preparation example is shown.

Preparation Example

(3) ##STR00003##

(4) One point two (1.20) grams of 4-Chloro-2-fluoro-5-(2-(ethoxycarbonyl)methoxy-3-pyridyloxy)aniline was added to a mixture of 18 ml of acetic acid and 2.7 ml of water at room temperature, followed by adding 572 mg of Potassium cyanate 572 mg thereto. The mixture was stirred at room temperature for 2 hours, and then the resulting mixture was concentrated under reduced pressure. The resulting residues were subjected to a silica gel column chromatography to give 1.10 g of the Present compound.

(5) .sup.1H-NMR (DMSO-D.sub.6) (ppm): 8.56 (1H, d, J=2.0 Hz), 7.91 (1H, d, J=7.7 Hz), 7.87 (1H, dd, J=5.0, 1.4 Hz), 7.56 (1H, d, J=10.9 Hz), 7.21 (1H, dd, J=7.9, 1.4 Hz), 6.99 (1H, dd, J=7.9, 5.0 Hz), 6.24 (2H, s), 4.93 (2H, s), 4.10 (2H, q, J=7.1 Hz), 1.15 (3H, t, J=7.1 Hz).

(6) Next, the rest example is shown.

(7) Test example 1: Test for controlling cucumber phytophthora blight fungi (Phytophthora capsici)

(8) Four point five (4.5) milligrams of the present compound was diluted with 100 L of dimethyl sulfoxide. One (1) L portion of the diluted liquid was dispensed into a titer plate (96 wells), and thereto was then dispensed 150 L of a potato dextrose broth medium (PDB medium) containing zoospores of cucumber phytophthora blight fungi (Phytophthora capsici). This plate was cultured at 27 C. for three days, thereby allowing the cucumber phytophthora blight fungi to undergo proliferation, and the absorbance at 600 nm of each well of the titer plate was then measured to determine a degree of growth of the cucumber phytophthora blight fungi. The efficacy was calculated from the determined degree of growth by the below-mentioned Equation 1. As a result, the efficacy of the Present compound was 90% or more.
Efficacy=100(XY)/XEquation 1
where
X: Degree of fungal growth in non-treated area
Y: Degree of fungal growth in treated area

(9) In the test example, a non-treated area means an area in which a test was conducted in the same manner, except that dimethyl sulfoxide was dispensed in place of the present compound diluted with dimethyl sulfoxide.

(10) Whilst, the similar test was conducted by using N-[4-chloro-2-fluoro-5-{2-(ethoxycarbonyl)methoxy-3-pyridyloxy}phenyl]acetamide which is described in EP patent No. 1122244 B2 instead of the present compound, and the efficacy thereof was less than 50%.

INDUSTRIAL APPLICABILITY

(11) The compound of the present invention has efficacies for controlling plant diseases, and is useful as an active ingredient for an agent for controlling plant diseases.