JPH04182403A - Germicide containing thiadiazole derivative as active ingredient - Google Patents

Abstract

PURPOSE:To obtain a germicide, containing a new thiadiazole derivative as an active ingredient and applicable to extermination and eradication of plant disease injuries due to various germs over a wide range without any phytotoxicity to cultivated crops at the normal concentration used. CONSTITUTION:A germicide containing a compound expressed by formula I [A is O or S; X, Y and Z are H, halogen, (halo)alkyl, alkoxy, OH or NO2; R1 is H, alkyl, alkenyl, alkynyl, formula II (n is 0 or 1; B is CH or N; R2 and R3 are H, halogen, alkoxy, NO2 or alkyl), formula III (R4 is H or alkyl; R5 is OH or substitutable NH2), formula IV (R9 and R10 are alkyl or alkoxy), formula V (W is O or S; E is CH2 or O; m is 0 or 1; R11 and R12 are alkyl), etc.] as an active ingredient.

Description

[Detailed description of the invention] [Industrial application field] The present invention relates to agriculturally useful fungicides.

[Prior Art] 1.2.5-Thiadiazole derivatives are described in, for example, the Journal of Organic Chemistry (Journa
l of Organic Chemistry) 2
823 (1967), etc., but 1,2
．． It is completely unknown that compounds having a 5-thiadiazole skeleton have bactericidal activity.

[Problem to be solved by the invention] Conventionally, many compounds with fungicidal activity have been used in the agricultural field, but there are problems such as the emergence of resistance in plant pathogenic bacteria due to continuous use of the same or the same type of chemicals for a long period of time. Various problems have been pointed out, and there is a desire for an excellent agricultural fungicide that does not cause the emergence of resistant bacteria.

[Means for Solving the Problems] The present inventors have discovered that a novel thiadiazole derivative discovered by the present inventors has excellent bactericidal activity, and have completed the present invention.

That is, the present invention provides a fungicide containing a thiadiazole derivative represented by the following general formula [I] as an active ingredient.

[However, in the formula, A represents an oxygen atom or a sulfur atom, and x
, ySz are the same or different and represent a hydrogen atom, a halogen atom, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a hydroxy group, or a nitro group, and R1 is a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group. group, an alkoxyalkyl group which may be substituted with an alkoxy group, an alkylthioalkyl group, (n represents O or 1, B represents CH or a nitrogen atom, R and R are the same or different and are a hydrogen atom, a halogen atom) , represents a lower alkoxy group, a nitro group, or a lower alkyl group optionally substituted with a halogen atom), -CHRC0R5 (R4 represents a hydrogen atom or a lower alkyl group, R5 represents a hydroxy group, or a lower alkyl group and/or or an amino group which may be substituted with a phenyl group), -COR6 (R8 is a lower alkyl group, a cycloalkyl group, or a lower alkyl group with one halogen atom).

Represents a phenyl group which may be substituted with a lower haloalkyl group, lower alkoxy group, nitro group or cyano group. ), -C(-W)NR7R8 (W represents an oxygen atom or a sulfur atom, R and R8 are the same or different and are a hydrogen atom, a lower alkyl group, or a cycloalkyl group.

a lower alkoxy group, an alkoxyalkyl group, a phenyl group which may be substituted with an alkoxy group, a pyridyl group which may be substituted with a halogen atom or a lower alkyl group, or (R and Rlo are the same or different and are a lower alkyl group,
Or represents a lower alkoxy group. ) represents.

), or (W represents an oxygen atom or a sulfur atom, E represents a CH2 or an oxygen atom, m is O or 1, and R11 and R12 are the same or different and represent a hydrogen atom or a lower alkyl group.) . ] [Function] The present invention will be described in detail below.

Table 1 below specifically shows the compounds of the present invention. The present invention is not limited only to these compounds.

Table 1 The agricultural and horticultural fungicide represented by the general formula of the present invention has excellent bactericidal activity against plant pathogens and can be applied to exterminate and eradicate plant diseases caused by a wide variety of fungi.

For example, rice blast disease (Pyricularia or
yzae), rice sheath blight (Rhizoctonia)
5olani), apple powdery mildew (Podospha
era Ieucotrjcha), apple scab (
Venturia 1naequalls), pear scab (Venturia nashlcola), pear sclerosis (Sclerosinlamall), oyster anthracnose (Gloeosporium kakl) S
Sclerotlnia cinerea
), peach scab (C1ad.).

sporium carpophllua), grape gray mold (Botrytis cinerea), grape smut (Elsinoe ampelina), grape late rot (Glomerella clngulat)
a), Cercospora bet
icola), peanut brown spot (Cercospo
ra arachidicola), Cercospora personata, Barley powdery mildew (Eryslphe gramini)
s f, sp, hordei), barley eye 0 spot disease (Cercosporella herpotri
choides), barley red snow rot (Fusari)
u* n1vale), wheat powdery mildew (Erysl
phe graminis f, sp, trtle
i) Wheat rust (Puccjnia reco)
ndlta), cucumber and disease (Pseudopero
nospora cubensis), cucumber powdery mildew (Sphaerotheca fuliglnea)
), cucumber vine blight (Mycosphaerella
5elonis), cucumber gray mold (Botry)
tis cinerea), cucumber scab (Clad
osporlum cucumerinum), tomato late blight (Phytophthora 1nfestans)
), tomato leaf mold (C1adosporius fu
lvu+g), Botrytls
cinerea), Powdery Mildew (Sphaer
otheca husull), hop botrytis (
Botrytis cfnerea), tobacco powdery mildew (Eryslphe cichoracearum)
, rose scab <D191 ocarpon rosae)
, mandarin scab (Elsjnoe favcetl)
l), tangerine blue mold (Penielljus Ha)
Ncum), citrus green mold (Penicllium
digItatυkai), etc. Among them, it is particularly effective against wheat powdery mildew, wheat rust, and rice blast.

In addition, these compounds have a good affinity for higher plants, that is, they do not cause any phytotoxicity to cultivated plants at normal concentrations, so they can be used as agricultural and horticultural fungicides to completely prevent plant diseases caused by pathogenic bacteria. It can be used conveniently.

Although the thiadiazole derivative itself may be used as the agricultural and horticultural fungicide of the present invention, it is usually mixed with a carrier, a surfactant, a dispersant, or an auxiliary agent and prepared in a conventional manner, for example, as a hydrating powder, an emulsion, or a thiadiazole derivative. It can be formulated and used as a powder or granules. These preparations can be diluted to appropriate concentrations and sprayed, or applied directly.

The blending ratio of the active ingredients may be selected as required, but a range of 0.5 to 80% based on the formulation is usually appropriate.

The application amount of the agricultural and horticultural fungicide of the present invention varies depending on the type of compound used, the target disease, the degree of damage, environmental conditions, the dosage form used, etc., but it can be used as is, such as powders and granules. In this case, the active ingredient is 0.1 per 10 ares.
It is best to select from the range of ~5 kg, preferably 0.3 ~ 1 seagull. In addition, when it is finally used in liquid form such as an emulsion or a wettable powder, the amount is 0.1 to 110,000 pp, preferably 1
It is preferable to select from the range of 0 to 3000 ppm.

[Example] Next, the agricultural and horticultural fungicide of the present invention will be specifically described with reference to Examples. Parts in the examples below refer to parts by weight.

Example 1 (Wettable powder) 10 parts of the compound of the present invention (No. 1) was used as a carrier material.
Clyte [trade name, manufactured by Kuniho Kogyo Co., Ltd.] 87.3 parts Neoperex [trade name, Kao Atlas (trade name) as surfactant]
Co., Ltd.] and 1.35 parts of Tsurupol 800A [trade name, manufactured by Toho Chemical Industries Co., Ltd.] were mixed and ground to obtain a 10% hydrating powder. Example 2 (emulsion) 5 parts of the compound of the present invention (No. 2) was mixed and dissolved with 85 parts of xylene and 10 parts of Tsurpol 800A as a surfactant,
A 5% emulsion was obtained.

Example 3 (powder) 2 parts of the compound of the present invention (No. 3) and 5 parts of diatomaceous earth.

and 93 parts of clay were uniformly mixed and ground to obtain a 2% powder.

Example 4 (granules) After mixing and pulverizing 10 parts of the compound of the present invention (No. 4) with 50 parts of bentonite, 35 parts of Kunilite [trade name, manufactured by Kunimine Kogyo Co., Ltd.] and 5 parts of Tsurupol 800A as a surfactant, 10 parts of water was added, stirred uniformly, extruded through a sieve hole with a diameter of 0.71 mm, dried, and cut into lengths of 1 to 211 I11 to obtain 10% granules.

Next, test examples will be given to further clarify the usefulness of the compound of the present invention as an agricultural and horticultural fungicide.

Test Example 1 Wheat powdery mildew preventive effect test Wheat seeds (variety: Norin No. 61) were sown in 8 cm x 8 cm plastic pots and grown in a greenhouse. A solution obtained by diluting a hydrating powder prepared according to Example 1 with water to an active ingredient concentration of 500 ppm was sprayed onto wheat seedlings whose leaves had fully expanded. After air-drying, it was inoculated with wheat powdery mildew and placed in a constant temperature room at 25°C. Seven days after inoculation, the degree of damage to the entire pot was investigated according to the following criteria, and the control value was calculated.

Degree of damage (%) - N N: Total number of leaves examined nO Number of leaves without disease nl: Number of affected leaves with a lesion area rate of less than 25% n2: Number of affected leaves with a lesion area rate of 25 to 50% n3: Diseased leaves Spot area rate 50-75
Number of diseased leaves in % n4: Number of diseased leaves with lesion area ratio of 75% or more Control value (%) - Degree of damage in untreated plot The results obtained are shown in Table 2.

Table 2 Test Example 2 Wheat Rust Preventive Effect Test Wheat seeds (variety = m-lin No. 61) were sown in 8 cm x 8 cm plastic pots and grown in a greenhouse. A solution obtained by diluting a hydrating powder prepared according to Example 1 with water to an active ingredient concentration of 500 ppm was sprayed onto wheat seedlings whose leaves had fully expanded. After air-drying, it was inoculated with wheat rust and placed in a constant temperature room at 25°C. Seven days after inoculation, the number of lesions throughout the pot was investigated, and the control value was calculated according to the following formula.

Control value (%) - (1-number of lesions in treated area, X□.

Number of lesions in untreated area The results obtained are shown in Table 3.

Test Example 3 Rice blast preventive effect test Rice seeds (variety: Yamahoshi) were sown in 8 cm x 8 cm plastic pots and grown in a greenhouse. 2.5~
At the third leaf stage, a solution prepared by diluting a hydrating powder prepared according to Example 1 with water to an active ingredient concentration of 500 pI'm was sprayed. After air-drying, the rice blast fungus was inoculated and placed in a constant temperature room at 25°C.

Seven days after inoculation, the number of lesions throughout the pot was investigated, and the control value was determined using the same formula as in Test Example 2.

The results obtained are shown in Table 4.

Table 4

Claims (1)

[Claims] (1) General formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼[I] [However, in the formula, A represents an oxygen atom or a sulfur atom, and
, Y, and Z are the same or different and represent a hydrogen atom, a halogen atom, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a hydroxy group, or a nitro group, and R_1
is a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, an alkoxyalkyl group that may be substituted with an alkoxy group, an alkylthioalkyl group, ▲ Numerical formulas, chemical formulas, tables, etc. ▼ {n represents 0 or 1 , B represents CH or a nitrogen atom, R_2 and R_3 are the same or different hydrogen atoms,
Represents a halogen atom, a lower alkoxy group, a nitro group, or a lower alkyl group optionally substituted with a halogen atom. }, -CHR_4COR_5{R_4 represents a hydrogen atom or a lower alkyl group, and R_5 represents a hydroxy group or an amino group which may be substituted with a lower alkyl group and/or a phenyl group. }, -COR_6 (R_6 represents a lower alkyl group, a cycloalkyl group, or a phenyl group which may be substituted with a halogen atom, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a nitro group, or a cyano group.), - C(=W)NR_7R_8 {W represents an oxygen atom or a sulfur atom, and R_7 and R_8 are the same or different and substituted with a hydrogen atom, a lower alkyl group, a cycloalkyl group, a lower alkoxy group, an alkoxyalkyl group, or an alkoxy group. a phenyl group that may be substituted with a halogen atom or a lower alkyl group, or a ▲ mathematical formula, chemical formula, table, etc. ). }, or ▲There are mathematical formulas, chemical formulas, tables, etc.▼ {W represents an oxygen atom or a sulfur atom, E represents a CH_2 or an oxygen atom, m is 0 or 1, R_1_1, R
_1_2 are the same or different and represent a hydrogen atom or a lower alkyl group. } represents. ] A disinfectant containing a thiadiazole derivative represented by the following as an active ingredient.