JPS59212410A - Antifungal composition for agricultural and horticultural purposes - Google Patents

Abstract

PURPOSE:An antifungal composition for agricultural and horticultural purposes that contains a combination of a specific antifungal such as benzimidazol antifungal with an N-penylcarbamate, thus showing improved effect of combatting diseases in agricultural crops, especially antifungal effect against resistant strains. CONSTITUTION:The objective antifungal composition for agricultural and horticultural purposes contains, as active ingredients, (A) at least one of N-phenylcarbamates of formula I (R1-R3 are lower alkyl), e.g., the compound of formula IIand (B) at least one selected from benzimidazole antifungals of formula III, thiophenate antifungals of formula IV and cyclic imide antifungals of formula V. The resultant composition is effective against a wide range of filamentous fungi and further it shows high effectiveness in the fields where a fungus resistant to the above component B is formed and prevent the development of resistant strains in the fields where resistant strains are yet to be formed in a lower dose than that in case of sole use of individual components.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a compound of the general formula [I] [wherein R1, R2 and R8 are the same or different and represent a lower alkyl group. ] Regarding an agricultural and horticultural fungicidal composition containing as active ingredients 13 or more N-phenyl carbamate compounds represented by the following and one or more selected from benzimidazole fungicides, thiophanate fungicides, or cyclic imide fungicides. It is something.

Benzimidazole-based fungicides and thiophanate-based fungicides (hereinafter referred to as benzimidazole-thiophanate-based fungicides) have shown excellent control effects against various pathogenic bacteria that parasitize agricultural and horticultural crops, and have been used as official farm disinfectants since around 1970. It is widely used as a chemical agent and has greatly contributed to increasing crop production. However, when these fungicides are continuously sprayed on crops, drug-resistant bacteria become widespread, reducing the control effectiveness of the fungicides, often making them practically unusable. If spraying a fungicide does not produce the expected control effect and prevent disease outbreaks, farmers and other fungicide users will suffer severe damage. Furthermore, it is known that bacteria that are resistant to any of the benzimidazole thioph7ate fungicides are also resistant to other fungicides in this group, exhibiting so-called cross-resistance. Therefore, for example, in a field where no pesticidal effect is observed even after spraying Benomyl, no pesticidal effect can be expected even if other benzimidazole/thiophanate fungicides are sprayed. In fields where drug-resistant bacteria are prevalent, the use of benzimidazole/thiophanate fungicides must be discontinued, but there are many known cases in which the density of drug-resistant bacteria does not decrease even after discontinuing their use. If resistant bacteria emerge, the effects will be felt for a long time. In addition, in such fields, drug-resistant bacteria can be prevented by spraying other fungicides that do not show cross-resistance.
Although it is intended to control the target disease, very few benzimidazole/thiophanate fungicides exhibit excellent control effects, making accurate control difficult.

Cyclic imide fungicides are effective against various plant diseases, particularly gray mold, but they have the same problems with resistant bacteria as the benzimidazole thiophanate fungicides mentioned above.

In consideration of the above circumstances, the present inventors believe that a fungicide that exhibits a selective bactericidal effect against drug-resistant bacteria can be expected to have a high disease control effect in fields where drug-resistant bacteria occur, and therefore developed a fungicide that has such properties. He worked hard to invent the. As a result, it was found that the N-phenyl carbamate compound represented by the general formula [D] is a bactericidal agent that exhibits a strong bactericidal effect selectively against drug-resistant bacteria.

However, in actual fields where pathogens are prevalent, drug-resistant bacteria and wild bacteria (hereinafter referred to as
They are called susceptible bacteria. ) are often mixed, and benzimidazole/thiophanate fungicides or cyclic imide fungicides, or N represented by the general formula [I] above.
-It is difficult to expect sufficient disease control effects by using any of the phenyl carbamate compounds alone. Therefore, we investigated the disease control effect of using a mixture of one or more N-phenyl carbamate compounds and one or more benzimidazole/thiophanate fungicides or cyclic imide fungicides. The results show that the disease control effect is higher even at low concentrations when N-phenylcarbamate compounds, benzimidazole thiophanate fungicides, or cyclic imide fungicides are used in combination than when they are used alone. Became.

Therefore, the composition of the present invention has high practical value as a fungicide that exhibits excellent control effects in any type of environment. Furthermore, the composition of the present invention can be used even when there is concern about the spread of drug-resistant bacteria due to continuous spraying of benzimidazole-thiono-1-nate fungicides or cyclic imide fungicides in fields where drug-resistant bacteria have not appeared. , its appearance can be prevented.

As the N-phenyl carbamate compound represented by the general formula [11], f, for example, isopropyl N-(2-fluoro-3,4-
jetoxyphenyl) carbonate (hereinafter, compound a)
It is written as ), and benzimidazole fungicides include, for example, methyl 1-(butylcar)(moyl)benzimidazole-2-ylcano(mate (hereinafter referred to as compound A)), which is represented by the formula 0; 2-(4-thiazolyl)benzimidazole (hereinafter referred to as compound B), methylbenzimidazole-2-ylbamate (hereinafter referred to as compound C) represented by the formula, 2-( represented by the formula 2-Furyl) benzimidazole (hereinafter referred to as compound), and examples of thiophanate fungicides include 1 shown by the formula
, 2-bis(8-methoxycarbonyl-2-thioureido)benzene (hereinafter referred to as compound E), 1,2-bis(3-ethoxycarbonyl-2
-thiourido)benzene (hereinafter referred to as compound 1°).

), 2-(0,8-dimethylphosphorylamino) represented by the formula)
-1-(8'-methoxycarbonyl-2'-thioureido)benzene (hereinafter referred to as compound G), 2-(U, 0-dimethylthiophosphorylamino) -1-(8'-methoxy carbonyl-2-thioureido)benzene (hereinafter referred to as compound R),
In addition, as a cyclic imide fungicide, for example, N-C8',5'-dichlorophenyl)-1 shown by the formula
, 2-dimethylcyclopropano-1,2-calphokidiimide (hereinafter referred to as compound ①), as shown by the formula 8-(8', 5'-dichlorophenyl)-1-isopropylic compound ? Dacilidine-2
, 4-dione (hereinafter referred to as compound J), 8'-(8',5'-dichlorophenyl)-
5-Methyl-5-vinyloxazolidine-2゜4-dione (hereinafter referred to as "l!" in the compound), ethyl (R8)-8-(8', 5'-dichlorophenyl)-5- represented by the formula Methyl-2,4-dioxoxazolidine-5
-carboxylate (hereinafter referred to as compound).

Since the composition of the present invention has excellent bactericidal activity against a wide variety of filamentous fungi, it can be used to control various pathogens occurring in agriculture and horticulture.

For example, powdery mildew of apples (Podosphae
raLeoucotricha), Sclerosis fungus (Ve
nturia 1naecualis), Gloeosporium kaki on oysters, Gloeosporium kaki on oysters, Clerotinia cinere on peaches (8clerotinia cinere)
a), Oladosporium carp
pophilum), grape botrytis fungus (Bot
rytiscinerea), Els
inoe ampeline), Glo
rnerella cingulata), Cercsspora beticala
), peanut brown spot fungus (Cercospora
arachidicola), Cercos
pora personata), barley powdery mildew (Erysiphe graminis f, s
P. hordei), eye spot fungus (Cer.
cosporella, berpotrichoid
es), Fusarium n1v
ale), wheat powdery mildew (Erysiphe
graminio f, sp, tritici)
, cucumber powdery mildew (5phaerotheca
fuliginea), Vine blight fungus (Mycosp)
haerella melonis), Botrytis cinerea, Cladosporium cucumerineem
), tomato leaf mold fungus (Cladosporium
S.

fulvum), gray mold fungus (Botrytia
clnerea), strawberry powdery mildew fungus (8ph
aerotheca humuli ), Botrytis cinerea on hops, and Erysiphe cichor on tobacco.
acearum), rose scab fungus (Diploca
rpon rosae), mandarin orange scab fungus (El
sinde fawcetti), P. sinde fawcetti (P.
enicillium italicum), green mold fungus (Penicillium digitatum)
), it can be used to control drug-resistant bacteria such as.

On the other hand, it has also been found that the composition of the present invention is highly safe for humans, livestock, and fish, and can be used without causing any practical harm to agriculturally useful crops. When actually applying the composition of the present invention, it can be used as it is without adding other ingredients, or it can be mixed with a carrier to make it easier to use as a fungicide. For example, powders, wettable powders, oils, emulsions, tablets, granules, fine granules,
It is formulated into aerosols, flowables, etc. and applied.

The above preparations generally contain active compounds (including mixed ingredients).
1.0 to 95.0%, preferably 2.0 to 95.0% by weight
Contains 80.0%, usually 10 to 100 per 10 ares
An application amount of 1.5 g is appropriate.

Furthermore, the concentration used is preferably in the range of 0.005% to 0.5%, but the amount and concentration used will vary depending on the dosage form, application period,
Since it varies depending on the method, location, target disease, target crop, etc., there is no problem in increasing or decreasing the amount without being limited to the above range.

Furthermore, it can be used in combination with other fungicides, herbicides, plant growth regulators and insecticides.

1 word 8 / 71/ v Jl/-buti 71/
8-p-tert-butylbenzyldithiocarbonimidate, 01O-dimethyl U-(2,6-dichloro-4-methylphenyl)phosphorothioate, N-
Trichloromethylthio-4-cyclohexene-1゜2-
Dicarboximide, polyoxin, stolebutomycin, cinque ethylene bisdithiocarbamate, tetrachloroisophthalonitrile, 8-hydroxyquinoline,
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
- Fungicides such as methylglycinate and aluminum ethyl phosphite, 2.

Phenoxy-based removal such as 4-dichlorophenoxyacetic acid Ju1
1.2.Diphenyl ether herbal agents such as 4-dichlorophenyl 4'-nitrophenyl ether, 2-chloro-4.
Triazine herbicides such as 6-pisethyl JL amino-1,8.5-1-riazine, urea herbicides such as 3-(8,4-dichlorophenyl)-111-dimethylurea, isopropyl N-(3-chloro Carbamate herbicides such as phenyl) carno mate, S-(4-chlorobenzyl)
Thiol carbamate herbicides such as N,N-diethylthiolcarano (mate), 3.

Acid anilide herbicides such as 4-dichloropropionanilide, uracil herbicides such as 5-bromo-3-sec-butyl-6-methyluracil, 1.

Pyridinium salt herbicides such as 1'-dimethyl-4,4'-bipyridinium chloride, N-(phosphonomethyl)
Glycine, 〇-Ethyl 0-(2-nitro-5-methylphenyl) N-sec-phthylphosphoramidothioate or 5-(2-methyl-1-piperidylcarbonylmethyl)0゜O-di-n - Phosphorus herbicides such as propyl dithiophosphate, toluidine herbicides such as α,α,α-trifluoro2゜6-sinitroN, N-dipropyl-P-toluidine, 0.0-dimethyl 0-
Organophosphorus insecticides such as (4-nitro-3-methylphenyl) phosphorothioate, α-cyano-3-phenoxybenzyl 2-(4-talolophenyl)isovalerate,
3-phenoxybenzyl 2,2-dimethyl-8-(2,
2 dichlorohinyl) cyclopropane carboxylate,
It can be used in combination with pyrethroid insecticides such as α-cyano-8-phenoxybenzyl 2゜2-dimethyl-8-(2,2-dibromohinyl) dichloropropanecarboxylate, and each single agent can control There is no reduction in the effect, and furthermore, a synergistic effect by mixing is expected.

Next, test examples and formulation examples will be given to further clarify the usefulness of the compounds of the present invention as agricultural and horticultural fungicides.

Test Example 1 Cucumber Powdery Mildew Control Effect A 90-capacity plastic bottle was filled with sandy loam, and cucumbers (variety: Sagami Hanjiro) were sown. This was cultivated at room temperature for 8 days to obtain cucumber seedlings with expanded cotyledons. To these seedlings, a water-diluted solution of the test compound in the form of a wettable powder was sprayed on the foliage until a sufficient amount of droplets adhered to the leaf surface. After air-drying the chemical solution, the seedlings were infected with cucumber powdery mildew fungus (8phaerotheca fu).
liginea) (y) A conidial suspension obtained by mixing drug-resistant bacteria and susceptible bacteria was spray inoculated. The plants were placed in a greenhouse and cultivated for 10 days to develop the disease, and then the disease state was observed.

The disease severity was calculated by the following method.

That is, depending on the appearance of lesions on the investigated leaves, 0°0.5, 1
, 2, and 4, and the disease severity was calculated using the following formula.

(Sickness index) (Sickness status) 0...
...No bacterial flora or lesions are observed on the leaf surface.

0.5: Bacterial flora or lesions are observed on the leaf surface in less than 5% of the leaf area.

1...Bacterial flora or lesions are observed on the leaf surface in less than 20% of the leaf area.

2: Bacterial flora or lesions are observed on the leaf surface in less than 50% of the leaf area.

4...Bacterial flora or lesions are observed on the leaf surface over 50% of the leaf area.

Next, calculate the pest control value using the following formula.

As a result, as shown in Table 1, compound a, compounds A, B,
When sprayed in combination with any of C, D, E, F, G, and H+7), superior control efficacy5 was observed compared to when they were sprayed alone.

Table 1 Test Example 2 Tomato gray mold control effect A 90 ml plastic pot was filled with sandy loam, and tomatoes (Shinzuke: Fukuju No. 2) were sown. This was cultivated in a ditch room for 4 weeks to obtain tomato plants at the 4-leaf stage. A water diluted solution of the test compound in the form of an emulsion or wettable powder is added to this in a pot.
Sprayed on stems and leaves at 0me. After air-drying the chemical solution, gray mold fungus (
A conidial liquid obtained by mixing drug-resistant and susceptible bacteria of Botrytis cinerea) was spray inoculated. .

This was placed in a humid room at 20°C for 5 days and the disease development state was observed. The disease onset investigation method and control value calculation were performed in the same manner as in Test Example 1.

As a result, as shown in Table 2, compound a and compound I, , J,
When sprayed in combination with any of L, superior pesticidal effects were obtained compared to when they were sprayed alone.

Table 2 Formulation Example 1 Powder 31 parts of the compound, 11 parts of the compound, 88 parts of clay and 10 parts of talc are thoroughly ground and mixed to obtain a powder with a base ingredient content of 2%.

Formulation Example 2 Wettable powder compound 820 parts, compound JIO part, diatom ±45 parts, white carbon 20 parts, wetting agent (sodium lauryl sulfate) 8 parts
1 part and 2 parts of a dispersant (calcium lignin sulfonate) are thoroughly ground and mixed to obtain a wettable powder having a base ingredient content of 30%.

Formulation example 3 810 parts of wettable powder compound, 40 parts of compound A, 45 parts of diatomaceous earth, wet a
2.5 parts of agent (calcium alkylbenzenesulfonate) and 2.5 parts of dispersant (calcium ligninsulfonate)
By thoroughly pulverizing and mixing the two parts, a wettable powder having a main ingredient content of 50% can be obtained.

Sumitomo 4-2-1 Takashi, Takarazuka City Sumitomo 4-2-1 Takashi, Takarazuka City Within Kagaku Kogyo Co., Ltd. 57-

Claims (1)

[Claims] General formula [wherein R1, R2 and R8 are the same or different and represent a lower alkyl group. ] Agricultural and horticultural use characterized by containing one or more R-phenyl carbamate compounds represented by the following and one or more benzimidazole fungicides, thiophanate fungicides, or cyclic imide fungicides as active ingredients. Sterilizing composition.