JPH0532507A - Germicidal composition for agriculture and horticulture - Google Patents

Abstract

PURPOSE:To provide a germicidal composition for agriculture and horticulture, exhibiting an excellent control effect even in fields containing mixed resistant fungi. CONSTITUTION:An agricultural and horticultural germicidal composition contains (A) one kind or more of N-phenylcarbamate compounds of formula I (R is lower alkyl, lower alkenyl, lower alkinyl, lower haloalkyl, lower haloalkinyl, phenyl-substituted lower alkyl; Z is H, lower alkyl carbonyl, lower cycloalkylcarbonyl, benzoyl capable of having a hologen atom) and (B) one kind or more of cyclic imide germicides of formulas II, III, IV, and V as active ingredients, and exhibits a high blight control effect even in lower concentrations than the case when the components A and B are separately used, respectively. The composition exhibits the excellent blight control effect even in any field, and can especially previously prevent the generation of chemical-resistant fungi, even when the epidemy of the chemical-resistant fungi is feared by continuously applying benzimidazole.thiophanate germicides or the cyclic imide germicides to fields which are upto data free from the generation of the chemical-resistant fungi.

Description

Detailed Description of the Invention

[0001]

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

[0002]

[Chemical 2]

[In the formula, R represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower haloalkyl group, a lower haloalkynyl group, or a phenyl-substituted lower alkyl group, Y represents an oxygen atom or a sulfur atom, and Z represents Z.
Represents a hydrogen atom, a lower alkylcarbonyl group, a lower cycloalkylcarbonyl group, or a benzoyl group optionally substituted with a halogen atom. ] N-
At least one phenylcarbamate compound, and N-
(3 ', 5'-dichlorophenyl) -1,2-dimethylcyclopropane-1,2-dicarboximide, 3-
(3 ', 5'-Dichlorophenyl) -1-isopropylcarbamoylimidazolidine-2,4-dione, 3-
(3 ', 5'-dichlorophenyl) -5-methyl-5-
Vinyloxazoline-2,4-dione or ethyl (R, S) -3- (3 ', 5'-dichlorophenyl)-
A fungicidal composition for agricultural and horticultural use, which comprises, as an active ingredient, at least one selected from the group of cyclic imide fungicides consisting of 5-methyl-2,4-dioxooxazolidine-5-carboxylate. It is about things.

[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. Cyclic imide fungicides are effective against various plant diseases, especially Botrytis cinerea, but they have the same problem of resistant bacteria as the above-mentioned benzimidazole thiophanate fungicides. In consideration of the above circumstances, the present inventors have made diligent efforts to develop a bactericide showing a bactericidal effect selectively against drug-resistant bacteria, and as a result, the above-mentioned general formula
It has been revealed that the N-phenylcarbamate compound represented by Chemical formula 2 is a bactericidal agent having a strong bactericidal effect selectively against drug-resistant bacteria. However, in an actual field where pathogenic bacteria are prevalent, drug-resistant bacteria and wild-type bacteria (hereinafter referred to as susceptible bacteria) sensitive to benzimidazole / thiophanate fungicides or cyclic imide fungicides are mixed. In many cases, a cyclic imide-based germicide or the above-mentioned general formula 2
It is difficult to say that a sufficient disease control effect is necessarily obtained only by using any one of the N-phenyl carbamate compounds represented by.

[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 N-phenyl carbamate compounds represented by and (b) N- (3 ′, 5′-dichlorophenyl) -1,
2-Dimethylcyclopropane-1,2-dicarboximide, 3- (3 ', 5'-dichlorophenyl) -1-isopropylcarbamoylimidazolidine-2,4-dione, 3- (3', 5'-dichlorophenyl) -5-Methyl-5-vinyloxazoline-2,4-dione or ethyl (R, S) -3- (3 ', 5'-dichlorophenyl) -5-methyl-2,4-dioxooxazolidine-
A N-phenylcarbamate compound represented by the above general formula 2 or a cyclic imide fungicide, which is used by mixing with one or more kinds selected from the group of cyclic imide fungicides consisting of 5-carboxylate. The present invention was found to exhibit a high disease control effect at a low concentration when both are used in combination as compared with the case where they are used 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, in the field where the drug-resistant bacteria have not appeared, even when the spread of drug-resistant bacteria is feared by continuously spraying the benzimidazole thiophanate fungicide or the cyclic imide fungicide, Appearance can be prevented.

Some of the N-phenylcarbamate compounds represented by the general formula 2 used in the present invention are shown in Tables 1 and 2.

[0008]

[Table 1]

[0009]

[Table 2]

Next, Table 3 shows some of the cyclic imide fungicides used in the present invention.

[0011]

[Table 3]

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 which 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 and α-cyano-3-phenoxybenzyl 2,2-dimethyl-3- (2,2-dibromovinyl) diclopropanecarboxylate. It can be used as a mixture with a system insecticide, and none of them reduces the control effect of each single agent, and further, a synergistic effect by mixing is expected.

[0016]

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 the compound numbers and compound symbols in Table 1, Table 2 and Table 3.

First, formulation examples are shown. Formulation Example 1 Powder Compound 1 (1 part), Compound I (1 part), Clay (88
Parts) and talc (10 parts) are well pulverized and mixed to obtain a powder having a main ingredient content of 2%.

Formulation Example 2 Wettable powder Compound 6 (20 parts), Compound J (10 parts), diatomaceous earth (4 parts)
5 parts), white carbon (20 parts), wetting agent (sodium lauryl sulfate) (3 parts) and dispersant (calcium lignin sulfonate) (2 parts) are well pulverized and mixed to obtain a wettable powder containing 30% of the main agent. To get

Formulation Example 3 Wettable powder Compound 7 (10 parts), Compound K (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.

Formulation Example 4 Wettable powder Compound 8 (25 parts), Compound I (50 parts), diatomaceous earth (1
8 parts), wetting agent (calcium alkylbenzene sulfonate) (3.5 parts) and dispersant (calcium lignin sulfonate) (3.5 parts) are mixed well and the main agent content is 7
5% of wettable powder is obtained.

Formulation Example 5 Wettable powder Compound 1 (20 parts), Compound L (30 parts), powdered sucrose, (40 parts), white carbon (5 parts), 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 50%.

Next, test examples will be shown. Test Example Tomato gray mold control effect A 90 ml plastic pot was filled with sandy loam and sown with tomato (cultivar: Fukuju No. 2). This was cultivated in a greenhouse for 4 weeks to obtain 4-leaf stage tomato seedlings. Add 10 ml of a diluted solution of the test compound in emulsion or wettable powder to each pot.
It was sprayed on the foliage. After air-drying the chemical solution, Botryt
is cinerea) was spray-inoculated with conidial fluid obtained by mixing drug-resistant bacteria and susceptible bacteria. This was left under humid conditions at 20 ° C. for 5 days, and then the disease state was observed. The disease severity was calculated by the following method. That is, according to the appearance of lesions on the surveyed leaves, they are classified into indices of 0, 0.5, 1, 2, and 4,
The disease severity 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 found 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 observed on the leaf surface in 50% or more of the leaf area. Subsequently, the control value was calculated from the following formula. The results are shown in Tables 4-7.

[0023]

[Table 4]

[0024]

[Table 5]

[0025]

[Table 6]

[0026]

[Table 7]

[0027]

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.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁵ Identification code Internal reference number FI technical display location (A01N 47/20 33:08) (72) Inventor Yukio Ishiguri 4-2 Takashi, Takarazuka-shi, Hyogo Prefecture No. 1 Sumitomo Kagaku Kogyo Co., Ltd. (72) Inventor Shigeo Yamamoto 4-2-1 Takashi Takarazuka-shi, Hyogo Sumitomo Kagaku Kogyo Co., Ltd. (72) Inventor Katsuzo Kamoshita 4-2 Takashi, Takarazuka-shi, Hyogo No. 1 Sumitomo Chemical Co., Ltd.

Claims (1)

What is claimed is: (a) General formula (1) [Wherein R represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower haloalkyl group, a lower haloalkynyl group or a phenyl-substituted lower alkyl group, and Y
Represents an oxygen atom or a sulfur atom, Z represents a hydrogen atom,
It represents a lower alkylcarbonyl group, a lower cycloalkylcarbonyl group, or a benzoyl group optionally substituted with a halogen atom. ] One or more of the N-phenyl carbamate compounds represented by the following, and (b) N- (3 ', 5'-dichlorophenyl) -1,2.
-Dimethylcyclopropane-1,2-dicarboximide, 3- (3 ', 5'-dichlorophenyl) -1-isopropylcarbamoylimidazolidine-2,4-dione, 3- (3', 5'-dichlorophenyl)- 5-Methyl-5-vinyloxazoline-2,4-dione or ethyl (R, S) -3- (3 ', 5'-dichlorophenyl) -5-methyl-2,4-dioxooxazolidine-
A sterilizing composition for agricultural and horticultural use, which comprises, as an active ingredient, one or more kinds selected from the group of cyclic imide-based bactericides composed of 5-carboxylate.