JPH0558823A - Agricultural and hotricultural fungicide composition - Google Patents

Abstract

PURPOSE:To obtain an agricultural and horticultural composition exhibiting excellent controlling effects even in a field having agent-resistant microorganisms by combining a specific aniline derivative with a specific thiophanate-based fungicide. CONSTITUTION:An agricultural and horticultural composition comprising (A) one or more aniline derivatives shown by formula I [X and Y are lower alkyl; (k), (l), (m) and (n) are 0 or 1; R<1> is lower alkyl, lower alkoxy or lower alkoxymethyl; Z is H; A is 0; B is W-R<4> (W is O; R<4> is lower alkyl)] and (B) one or more selected from a thiophanate-based fungicide group composed of compounds shown by formula II, formula II, formula IV and formula V. The composition has high safety to human, animals and fishes and is usable without practically damaging crops important in terms of agriculture.

Description

Detailed Description of the Invention

[0001]

The present invention relates to (a) the general formula:

[0002]

[Chemical 2]

[Wherein X and Y are the same or different,
A lower alkylene group is shown. k, l, m and n are the same or different and represent 0 or 1. R ¹ represents a lower alkyl group, a lower alkoxyl group, or a lower alkoxymethyl group. Z represents a hydrogen atom. A represents an oxygen atom.
B represents a group represented by the general formula —W—R ⁴ . (Wherein W represents an oxygen atom, and R ⁴ represents a lower alkyl group.)],
(B) 1,2-bis (3-methoxycarbonyl-2-thioureido) benzene, 1,2-bis (3-ethoxycarbonyl-2-thioureido) benzene, 2- (O, S)
-Dimethylphosphorylamino) -1- (3'-methoxycarbonyl-2'-thioureido) benzene and 2-
(O, O′-dimethylthiophosphorylamino) -1-
A sterilizing composition for agricultural and horticultural use, which comprises, as an active ingredient, at least one selected from the group of thiophanate-based bactericides comprising (3'-methoxycarbonyl-2'-thioureido) benzene. is there.

[0004]

2. Description of the Related Art Benzimidazole fungicides and thiophanate fungicides (hereinafter referred to as benzimidazole thiophanate fungicides) have excellent control effects against various pathogenic fungi parasitic on agricultural and horticultural crops. Since around this time, it has been widely used as a fungicide for agriculture and horticulture, and has greatly contributed to increased crop production.

[0005]

However, when these fungicides are continuously sprayed on crops, drug-resistant bacteria spread,
The control effect of chemicals has decreased, and it has become more and more common that the medicine becomes practically unusable. If a disinfectant is not sprayed and the expected control effect is not obtained and the occurrence of disease cannot be suppressed, the damage to the users of the drug such as farms will be great. Further, it is known that a bacterium which is resistant to any one of the benzimidazole / thiophanate fungicides becomes resistant to other fungicides in this group and exhibits so-called cross resistance. Therefore, for example, in the field where the control effect is not recognized even when spraying benomyl which is a commercially available agent, the control effect cannot be expected even if other benzimidazole / thiophanate fungicides are applied. In fields where drug-resistant bacteria are prevalent, the use of benzimidazole / thiophanate fungicides has to be discontinued, but there are many cases in which the density of drug-resistant bacteria does not decrease even after discontinuation of use. When resistant bacteria develop, they will be affected for a long time thereafter. Moreover, in such fields, the target disease is controlled by spraying a fungicide of another strain in which the drug-resistant bacterium does not show cross resistance. However, the benzimidazole / thiophanate fungicide has a better control. Very few of them are effective, making proper control difficult. In consideration of the above circumstances, the inventors of the present invention have made diligent efforts to develop a bactericide exhibiting a selective bactericidal effect against drug-resistant bacteria. As a result, the aniline derivative represented by the general formula 2 is selected as a drug-resistant bacterium. It was found to be a bactericidal agent having a strong bactericidal effect. However, in an actual field where pathogenic bacteria are prevalent, it is often the case that drug-resistant bacteria and wild-type bacteria (hereinafter referred to as susceptible bacteria) that are sensitive to benzimidazole / thiophanate fungicides coexist, and benzimidazole. -It is difficult to say that a sufficient disease control effect is necessarily obtained by using either the thiophanate fungicide or the aniline derivative represented by the general formula 2 alone.

[0006]

Under the above circumstances, as a result of various studies, the present inventors have found that (a) the general formula
One or more of the aniline derivatives represented by (b) 1,2-
Bis (3-methoxycarbonyl-2-thioureido) benzene, 1,2-bis (3-ethoxycarbonyl-2-)
Thioureido) benzene, 2- (O, S-dimethylphosphorylamino) -1- (3'-methoxycarbonyl-
2'-thioureido) benzene and 2- (O, O'-
Dimethylthiophosphorylamino) -1- (3′-methoxycarbonyl-2′-thioureido) benzene mixed with one or more selected from the group of thiophanate-based fungicides to use the above-mentioned general formula The inventors have found that when the aniline derivative or the thiophanate-based fungicide represented by Chemical formula 2 is used as a mixture of both, it exhibits a high disease control effect even at a low concentration, as compared with the case of using the fungicide alone. Therefore, the composition of the present invention has a high practical value as a bactericide having an excellent controlling effect in any field. Furthermore, the composition of the present invention prevents the appearance of drug-resistant bacteria even in the field where no drug-resistant bacteria have appeared, even when the spread of drug-resistant bacteria is feared by continuously spraying the benzimidazole / thiophanate fungicide. be able to.

Table 1 shows some of the aniline derivatives represented by the general formula 2 used in the present invention.

[0008]

[Table 1]

Next, Table 2 shows the thiophanate fungicides used in the present invention.

[0010]

[Table 2]

Since the composition of the present invention has excellent bactericidal activity against a wide variety of filamentous fungi, it can be used for controlling various pathogenic fungi that occur in agriculture and horticulture. For example, powdery mildew of apple (Podosphaera leoucotricha), scab (Venturia inaecualis), monili (Scleroti)
nia mali), oyster anthracnose (Gloeosporium kaki), peach scab (Sclerotinia cinerea), scab (Clad)
osporium carpophilum), grapevine Botrytis cinerea (Botr
ytis cinerea), black wilt (Elsinoe ampeline), late rot (Glomerella cingulata), sugar beet leaf spot (Cercospora beticala), peanut leaf spot (Cerc)
ospora arachidicola), black rot (Cercospora persona)
ta), powdery mildew of barley (Erysiphegraminis fs
p.hordei), eye spot disease fungus (Cercosporella herpo
trichoides), red snow rot (Fusarium nivale), and powdery mildew of wheat (Erysiphe graminio f.sp.tritici)
, Powdery mildew of cucumber (Sphaerotheca fuliginea)
, Blight fungus (Mycosphaerella melonis), Botrytis cinerea (Botrytis cinerea), Black scab (Cladosporium c)
ucumerineem), tomato leaf mold fungus (Cladosporium ful)
vum), Botrytis cinerea), strawberry powdery mildew (Sphaerotheca humuli), hop Botrytis cinerea, tobacco powdery mildew (Er)
ysiphe cichoracearum), rose scab (Diplocarpo)
n rosae), mandarin orange fungus (Elsinoe faweetti),
Blue mold (Penicillium italicum), Green mold (Pe
nicillium digitatum), etc., and can be used for controlling drug-resistant bacteria.

On the other hand, the composition of the present invention has a high level of safety against human livestock and fish, and can be used with practically no harm to agriculturally useful crops.

When the composition of the present invention is actually applied, it can be used as it is without adding other components, or it is mixed with a carrier to make it easy to use as a bactericide, and it is usually used in a form such as powder or hydration. It is applied in the form of an agent, oil, emulsion, tablet, granule, fine granule, aerosol, flowable, etc. In the above-mentioned preparations, generally 1.0 to 95.0% by weight of active compound (including mixed components), preferably 2.0 to 80.0
%, Usually 10 to 100 g per 10 ares is suitable. Furthermore, its use concentration is 0.005% to 0.5.
% Range is desirable, but the amount and concentration of these are
Since it varies depending on the application time, method, place, target disease, target crop, etc., there is no problem in increasing or decreasing without regard to the above range.

It is also possible to use it in combination with other fungicides, herbicides, plant growth regulators and insecticides. For example, S-normal-butyl Sp-tert-butylbenzyldithiocarbonimidate, O, O-dimethyl O-
(2,6-Dichloro-4-methylphenyl) phosphorothioate, N-trichloromethylthio-4-cyclohexene-1,2-dicarboximide, polyoxine, streptomycin, zinc ethylene bisdithiocarbamate, tetrachloroisophthalonitrile, 8-hydroxy Quinoline, N'-dichlorofluoromethylthio-N,
N-dimethyl-N'-phenylsulfamide, 1- (4
-Chlorophenoxy) -3,3-dimethyl-1- (1,
2,4-triazol-1-yl) -2-butanone, methyl N- (2,6-dimethylphenyl) -N-methoxyacetyl-2-methylglycinate, aluminum ethyl phosphite and other fungicides, 2,4 -Phenoxy herbicides such as dichlorophenoxyacetic acid, diphenyl ether herbicides such as 2,4-dichlorophenyl 4'-nitrophenyl ether, 2-chloro-4,6-bisethylamino-1,3,5- Triazine herbicides such as triazine,
Urea herbicides such as 3- (3,4-dichlorophenyl) -1,1-dimethylurea, carbamate herbicides such as isopropyl N- (3-chlorophenyl) carbamate, S- (4-chlorobenzyl) N, Thiol carbamate herbicides such as N-diethyl thiol carbamate,
Acid anilide herbicides such as 3,4-dichloropropionanilide, uracil herbicides such as 5-bromo-3-sec-butyl-6-methyluracil, 1,1′-dimethyl-
Pyridinium salt herbicides such as 4,4′-bipyridinium chloride, N- (phosphonomethyl) glycine, O-ethyl O- (2-nitro-5-methylphenyl) N-sec
-Butylphosphoroamidothioate or S- (2-methyl-1-piperidylcarbonylmethyl) O, O-di-
phosphorus-based herbicides such as n-propyldithiophosphate,
α, α, α-trifluoro-2,6-dinitro-N, N
-Toluidine herbicides such as dipropyl-p-toluidine, organophosphorus insecticides such as O, O-dimethyl O- (4-nitro-3-methylphenyl) phosphorothioate, α
-Cyano-3-phenoxybenzyl 2- (4-chlorophenyl) isovalerate, 3-phenoxybenzyl 2,
Pyrethroids such as 2-dimethyl-3- (2,2-dichlorovinyl) cyclopropanecarboxylate-α-cyano-3-phenoxybenzyl 2,2-dimethyl-3- (2,2-dibromovinyl) diclopropanecarboxylate It can be used as a mixture with a system insecticide, neither of which reduces the control effect of each single agent, and further, a synergistic effect by mixing is expected.

[0015]

EXAMPLES The present invention will be described in more detail with reference to formulation examples and test examples. The compounds used in the formulation examples and test examples are shown by compound numbers and compound symbols in Tables 1 and 2.

First, formulation examples are shown. Formulation Example 1 Powder Compound 2 (2 parts), clay (88 parts) and talc (1 part)
If 0 part) is well pulverized and mixed, a powder having a main agent content of 2% is obtained.

Formulation Example 2 Wettable powder Compound 24 (30 parts), diatomaceous earth (45 parts), white carbon (20 parts), wetting agent (sodium lauryl sulfate) (3
Part) and dispersant (calcium lignin sulfonate)
If (2 parts) is well pulverized and mixed, a wettable powder having a main agent content of 30% is obtained.

Formulation Example 3 Wettable powder Compound 25 (50 parts), diatomaceous earth (45 parts), wetting agent (calcium alkylbenzene sulfonate) (2.5 parts) and dispersant (calcium lignin sulfonate) (2.5 parts) were well ground. When mixed, a wettable powder with a main agent content of 50% is obtained.

Formulation Example 4 Emulsion Compound 26 (10 parts), cyclohexanone 80 parts and emulsifier (polyoxyethylene alkylallyl ether)
If (10 parts) is well pulverized and mixed, an emulsifier having a main ingredient content of 10% is obtained.

Formulation Example 5 Powders Compound 2 (1 part), Compound E (1 part), Cray (88)
Parts) and talc (10 parts) are well pulverized and mixed to obtain a powder having a main ingredient content of 2%.

Formulation Example 6 Wettable powder Compound 26 (20 parts) Compound F (10 parts), diatomaceous earth (45 parts)
Part), white carbon (20 parts), a wetting agent (sodium lauryl sulfate) (3 parts) and a dispersant (calcium lignin sulfonate) (2 parts) are thoroughly pulverized and mixed to obtain a wettable powder having a main agent content of 30%. obtain.

Formulation Example 7 Wettable powder Compound 24 (10 parts), Compound G (40 parts), diatomaceous earth (4 parts)
5 parts), wetting agent (calcium alkylbenzene sulfonate) (2.5 parts) and dispersant (calcium lignin sulfonate) (2.5 parts) are mixed well, and the main agent content is 5
0% wettable powder is obtained.

Next, test examples will be shown. Test Example Cucumber Powdery Mildew Control Effect A 90 ml plastic pot was filled with sandy loam and sown with cucumber (variety: Sagamihanjiro). This was cultivated at room temperature for 8 days to obtain cucumber seedlings having cotyledons developed. This seedling was sprayed with an emulsion of an aniline derivative having the following compound number, a wettable powder of compounds E to H, and a water-diluted solution of a mixture thereof prepared according to Formulation Example 4 until the droplets adhered sufficiently to the leaf surface. did. After air-drying with a drug solution, seedlings were spray-inoculated with a conidia suspension obtained by mixing drug-resistant and susceptible bacteria of cucumber powdery mildew (Sphaerotheca fuliginea).
This was placed in a greenhouse and cultivated for 10 days to cause disease, and then the disease state was observed. The results are shown in Tables 3-4. The disease severity was calculated by the following method. That is, according to the appearance of lesions on the investigated leaves, the index was classified into 0, 0.5, 1, 2, 4 and the disease degree was calculated by the following formula. (Sickness index) (Sickness state) 0 ... No flora or lesions are observed on the leaf surface. 0.5 …… Microflora or lesions are observed on less than 5% of the leaf area on the leaf surface. 1 ...... A flora or lesion is observed on less than 20% of the leaf area on the leaf surface. 2 ...... The microflora or lesions are observed on less than 50% of the leaf area on the leaf surface. 4 ...... A flora or lesion is found on 50% or more of the leaf area on the leaf surface. Subsequently, the control value was calculated from the following formula.

[0024]

[Table 3]

[0025]

[Table 4]

[0026]

INDUSTRIAL APPLICABILITY The agricultural and horticultural germicidal composition of the present invention exhibits an excellent controlling effect even in a field where drug-resistant bacteria are mixed.

Front page continuation (72) Inventor Toshiro Kato 4-2-1 Takashi, Takarazuka-shi, Hyogo Sumitomo Kagaku Kogyo Co., Ltd.

Claims (1)

[Claims] 1. (a) General formula: ## STR1 ## [In the formula, X and Y are the same or different and each represents a lower alkylene group. k, l, m and n are the same or different,
Indicates 0 or 1. R ¹ represents a lower alkyl group, a lower alkoxyl group, or a lower alkoxymethyl group. Z is
Indicates a hydrogen atom. A represents an oxygen atom. B is a general formula −
The group represented by W—R ⁴ is shown. (Wherein W represents an oxygen atom, and R ⁴ represents a lower alkyl group)], and (b) 1,2-bis (3-methoxycarbonyl-2-). Thioureido) benzene, 1,2-bis (3-ethoxycarbonyl-2-thioureido) benzene, 2- (O, S
-Dimethylphosphorylamino) -1- (3'-methoxycarbonyl-2'-thioureido) benzene and 2-
(O, O′-dimethylthiophosphorylamino) -1-
A fungicidal composition for agricultural and horticultural use, which comprises, as an active ingredient, one or more kinds selected from the group of thiophanate-based fungicides consisting of (3'-methoxycarbonyl-2'-thioureido) benzene.