JPS5951208A - Fungicidal composition for agriculture and horticulture - Google Patents

Abstract

PURPOSE:The titled composition capable of being applied continuously, showing effects on fungi resistant to chemicals, obtained by combining an N-phenylthiocarbamate compound with a benzimidazole fungicide, a thiophanate fungicide or cyclic imide fungicide. CONSTITUTION:A fungicidal composition for agriculture and horticulture, comprising one or more of N-phenylthiocarbamate compounds shown by the formula I (X is halogen, or methyl; Y is halogen, methyl, alkoxy, etc.; Z is H, F, or alkoxy; A is O, or S; R is alkyl, alkenyl, alkynyl, alkoxy, etc.), and one or more of a benzimidazole fungicide (e.g., compound shown by the formula II, etc.), a thiophanate fungicide (e.g., compound shown by the formula III, etc.) and a cyclic imide fungicide (e.g., compound shown by the formula VI, etc.) as active ingredients. Having improved fungicidal effects on a wide range of various kinds of molds.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention is based on the general formula [wherein X represents a halogen atom or a methyl group]. Y represents a halogen atom, a methyl group, a lower alkoxyl group or a methoxymethyl group.

Z represents a hydrogen atom, a fluorine atom or a lower alkoxyl group. A represents an oxygen atom or a sulfur atom. R represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group, or a lower alkyl group substituted with any one of a lower alkoxyl group, a lower cycloalkyl group, a cyano group, and a halokene atom. ), such as N-phenylthiocarbamate compounds shown in Table 1, and pen-simidazole-based pesticides, such as methyl l-(butylcarbamoyl)benz of the formula % ( Imidazole-2-ylbamate (hereinafter compound fAI)
), 2-(4-thiazolyl)benzimidazole (hereinafter referred to as compound (Bl)) represented by the formula [
ol), 2-(2-furyl)benzimidazole (hereinafter referred to as Dl), or thiophanate fungicides, such as 1,2-bis(8-methoxycarbonyl) represented by the formula -2
-Thioureido)benzene (hereinafter referred to as compound (11))
, 1,2-bis(8-ethoxycarbonyl-
2-Thioureido)benzene (hereinafter referred to as compound IFI), 2-(0,8-dimethylphosphoryl-thioureido)benzene represented by the formula (hereinafter referred to as compound (0)), 2-(0 ,0-dimethylthiophosphorylamino)-1-(8'-methoxycarbonyl-2-thioureido)benzene (hereinafter referred to as compound (-11), or cyclic imide fungicide, for example, represented by the formula % formula % N-(8',5'-dichlorophenyl)-1
, 2-dimethylcyclopropane-1,2-carboximide (hereinafter referred to as compound (I)), 8-
(8', 5'-dichlorophenyl)-1-isobrobylcarbamoylimitasilidine-2,4-dione (
The compound (denoted as Jl) below, 8-(8',5'-dichlorophenyl)-5 represented by the formula
-Methyl-5-vinyloxazolidine-2゜4-dione (arranged with compound group)), ethyl (R
8) -8-(8', 5'-dichlorophenyl)-5-
An agricultural and horticultural fungicidal composition containing as an active ingredient methyl-2,4-dioxoxazolidine-5-carboxylate (hereinafter referred to as compound (Ll)) 4. (hereinafter referred to as the composition of the present invention).

Table l Benzimidazole fungicides and thiophanate fungicides (hereinafter referred to as pensimidazole-thiophanate fungicides) exhibit excellent control effects against various pathogenic bacteria parasitic on ornamental crops. It has been widely used as an agricultural and horticultural fungicide since around 1970, and has greatly contributed to increasing crop production. However, when these fungicides are continuously sprayed on crops, the resistance to the fungicides becomes widespread and the pest control effect of the fungicides decreases, often making them practically unusable. If spraying a fungicide does not have the expected control effect and the outbreak of the disease cannot be suppressed, the damage to farmers and other users of the fungicide will be enormous. Furthermore, it is known that bacteria that develop resistance to one of the benzimidazole/thiophanate fungicides also become 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/thiono-1-nate fungicides are sprayed.

In fields where drug-resistant bacteria are widespread, it is necessary to stop using benzimidazole-thiophyte fungicides, but there are many known cases where the density of drug-resistant bacteria does not decrease even after discontinuing their use. Therefore, once drug resistance develops, the effects will be felt for a long time. Also, in such fields, is it possible to control the target disease by spraying other fungicides to which drug-resistant bacteria do not show cross-resistance? There are very few species that show excellent control effects, making it difficult to control them accurately. The above-mentioned cyclic imide fungicides are effective against various plant diseases and gray mold;
There is a problem with resistant bacteria similar to that of Ne-1-based fungicides.

Considering the circumstances mentioned above, the present invention is limited by the fact that if there is a fungicide that shows a selective bactericidal effect against drug-resistant bacteria, it can be expected to have a high disease control effect in areas where drug-resistant bacteria develop. He worked hard to invent a pesticide that has the same properties. As a result, it was found that the aforementioned N-phenylthiocarbamate compound is a bactericidal agent that has a strong bactericidal effect selectively against drug-resistant bacteria. In other words, as is clear from the test examples described below, N-phenylthiocarbamate compounds are effective against diseases caused by wild bacteria that are susceptible to benzimidazole/thiophanate fungicides or cyclic imide fungicides (hereinafter referred to as drug-susceptible bacteria). Although it did not show any control effect, it showed an excellent control effect against diseases caused by drug-resistant bacteria, and its bactericidal activity against drug-resistant bacteria was extremely selective.

However, in actual fields where pathogenic bacteria are prevalent, drug-resistant and susceptible bacteria often coexist, and benzimidazole/thiophanate fungicides, cyclic imide fungicides, or - It is difficult to expect a sufficient disease control effect by using any one of the phenylthiocarbamate compounds alone.Therefore, one or more of the N-phenylthiocarbamate compounds and benzimidazole/thiophanate of [O] et al. We investigated the disease control effect of using a combination of N-phenylthiocarbamate-based compounds or benzimidazole/thiophanate-based fungicides. A higher tendency was observed when a fungicide or a cyclic imide fungicide was used in combination than when both were used alone.Therefore, the composition of the present invention has a strong bactericidal effect in any field. Furthermore, the composition of the present invention can be used to continuously spray benzimidazole-thiophanate fungicides or cyclic imide fungicides in fields where drug-resistant bacteria have not appeared. Even if there is a concern about the spread of gold, it is possible to prevent its appearance.

Since the composition of the present invention has strong bactericidal activity against a wide variety of filamentous species, it can be used to control various pathogenic bacteria that occur in agriculture and horticulture.

For example, powdery mildew of apples (pod OS p
h a-era 1eucotricha), Venturia 1na-equaIis
), Mycosphaerella pom
i), Marssonina mali
), 5clerotinia ma
li), oyster powdery mildew fungus (Phyllactin
ia kakicola), anthracnose (Oloeos
porium kaki), natural disease fungus of peach (5C
lerOLInla ctnerea), P. sclera (
Orado-sporium carpoph um)
, Phomopsis is sp.
, ), grape botrytis fungus (Botrytis
cinerea), Oercospora
viticnla ), powdery mildew (#ncinul
a necator), Elsinoe
ampelina), Glomerel
la cingulata), sugar beet brown spot fungus (
Qercospora beticola), Beannut brown spot madder (Qercospora arach)
idicola), Oercospor
a personata), Erysiphe graminis f, sp,
hordei), eye-spot fungi (Oercos
porella berpotr-1choides)
, Fusarium n1vake
, powdery mildew of wheat - (Erysiphe gram
inis f.

sp, tritici), cucumber powdery mildew fungus (5phaerotheca fuliginea)
), Mycosphaerella me
lonis), Sclerotinia fungi (5clerotinia)
sclerotiorum ), Botrytis blight (Ilo
trytis cinerea), Qlac
losporium cucumerinum), tomato leaf mold fungus (Olados-porium fu)
lvum), Botrytis di (Botrytisc)
inerea), eggplant black blight fungus (Oorynesp)
oramelongenae), strawberry powdery mildew (Sphaer-otheca humuli), and yellow wilt fungus (Fusarium nxys-porum f).
, sp. fragariae), onion gray rot fig (Botrytis alli),
Sclerotinia scle of lettuce
rotiorum), celery spot fungus (Oerc
ospora apii), common bean horn spot fungus (phaeoisariopsis griseola)
), Botrytis c.
inerea), tobacco powdery mildew (Erysi
phe cichoracearum), rose scab fungus (Diplocarpon rosae), mandarin scab F! 4 (Elsinae fawcett
i), blue mold 5H (Pencilales um i t
al icum ), penicilli fungus ( Penicilli
It can be used to control drug-resistant bacteria such as P. um digitatum).

On the other hand, it has also been found that the composition of the present invention has high safety against infestation and fish, and can be used without actually causing any harm to agriculturally useful crops. When the composition of the present invention is actually applied, it can be used in pure form without adding other ingredients, and it can also be used in a pure form without adding other ingredients. It can be applied by mixing with a carrier to make it easier to use as an i3 agent, and can be applied in the form of energized formulations, such as powders, wettable powders, ill formulations, emulsions, tablets, granules, fine granules, aerosols, flowables, etc. It can be used either way.

In the formulation, the amount of active compound (mixed ingredients in situ) by weight is generally between 1.0 and 95.096, preferably i, 12.0
~81), including 096, and usually an application pit with a diameter of 10 to 100F is appropriate. In addition, for historical use [the concentration is preferably in the range of 0.005 to 0.596, but these usage conditions, dosage form, application time, method, location, target title, companion crop, etc. There is no problem in increasing or decreasing the range without being limited to the above range.

Furthermore, it can be used in admixture with other fungicides, herbicides, plant growth regulators and insecticides, such as S-normal-butyl S-para-tert-butylbenzyldithiocarbonimidate, 0,0- Dimethyl 0-(2
,6-dichloro-4-methylphenyl) phosphorothioate, N-trichloromethylthio-4-cyclohexene-1,2-dicarboximide, cis-N-(1,1
,2,2-tetrachloroethylthio)-4-cyclohexene-1,2-dicarboximide, polyoxin, streptomycin, zinc ethylene bisdithiocarbamate, zinc dimethylthiocarbamate, manganese ethylenebisdithiocarbamate, bis(N,N-dimethylthio carbamoyl) disulfide, tetrachloroisophthalonitrile, 8-hydroxyquinoline, dodecylguanidiacetate, 5,6-sihydro-2-nonal-1,4-oxathiin-8-carboxanilide, N'
-dichlorofluoromethylthio-N,N-dimethyl-N
'-phenylsulfami)', 1-(4-chlorophenoxy)-8,8-dimethyl-1-(1,2゜4-triazol-1-yl)-2-butanone, methyl N-(2,
6-cystylphenyl)-N-methoxyacetyl-2-
Methylglycinate, aluminum ethyl phosphite disinfectant, 2,4-dichlorophenoxy vinegar 671.2
-,) 1 thyl-4-chlorophenoxylic acid, 2-methyl-4-chlorophenoxyacetic acid (ester, containing 4M)
phenoxy thread remover such as, 2,4-dichlorophenyl 4
'-nitrophenyl ether 2.4.6-) dichlorophenyl 4'-nitrophenyl ether, 2-chloro-4
-1-lifluoromethylphenyl 8'-ethoxy-4'
-nitrophenyl ether, 2,4-dichlorophenyl 4'-ditro-8-methoxyphenyl ether, 2゜4
-Diphenyl ether-based weeding f such as dichlorophenyl 8'-methoxycarbonyl-4-nitrophenyl ether
2-chloro-4,6-pisethylamino-1,8.
5-triazine, 2-chloro-4-ethylamino-6-
Isoprobylamino-1,8,5-triazine, 2-methylthio-4,6-pisethylamino-1,8.5-triazine, 2-methylthio-4,6-pisisopropylamino-1,8.5 - Triazine type +i such as triazine
4 Herbicide, 8-(8,4-cyanophenyl)-1,1-dimethylurea, 8-(8,4-dichlorophenyl)-1
Urea herbicides such as -methoxy-1-methylurea, t-(α,α-dimethylbenzyl)-ap-tolylurea, 1-\(2-benzothiazolyl)-t,a-dimethylurea, isopropyl N-( Carbamate thread clearing agents such as 3-chlorophenyl) carbamate, methyl N-(8,4-dichlorophenyl) carbamate, 5-(
Thiol carbamate herbicides such as (4-chlorobenzyl) N, N-diethylthiol carbamate, S-ethyl tA, N-hexamethylenethiol carbamate,
8.4-dichloropropionanilide, 2-chloro-N
-methoxymethyl-2,6-diethylacetanilide,
2-chloro-2'.

6'-Diethyl-N-(butoxymethyl)-acetanilide, 2-chloro-2,6-dinityl-N-(n-propoxyethyl)acetanilide, N-chloroacetyl-N-(2,6-dichlorophenyl)glycine Acid anilide herbicides such as ethyl ester, 11 pyridinium salt herbicides such as urapyridinium chloride such as 5-bromo-8-secondary-butyl-6-methyluracil, 3-cyclohexyl-5,6-drimethyleneuracil, etc. agent, N-(
phosphonomethyl)glycine, N.

N-his(phosphonomethyl)glycine, 0-ethyl 0
-(2-ditro-5-methylphenyl)N-secantarybutyl phosphoramidothioate, 5-(2-methyl-1-piperidylcarbonylmethyl) 0.0-
Di-n-propyldithiophosphate, 5-(2-methyl-l-biperidylcarponylmethyl) 0.0-di-
Phosphorus herbicides such as n-propyl dithiophosphate, 5-(2-methyl-1-piperidylcarbonylmethyl)0.0-diphenyl dithiophosphate, α, α, α
-Toluidine herbicides such as trifluoro 2゜6-sinitro N, N-dipropyl-p-toluidine, 5-tert-butyl-8-(2,4-dichloro-5-isopropoxyphenyl)-1,8, 4-Oxadiazoline-
2-one, 3-isopropyl-(IH)-2,1,8-
Benzothiadiazin-(8H)-one-2,2-dioxide, α-(β-naphthoxy)propionanilide, 4
-(2,4-dichlorobenzoyl)-1,8-dimethylpyrazol-5-yl p-toluenesulfonate, 8-
(Methoxycarbonylamino)phenyl 3-methylphenylcarbamate, 4-amino-3-methyl-6-phenyl-1,2,4-triazine, 0,0-dimethyl 0
-(4-nitro-3-methylphenyl) phosphorothioate, 0-(4-cyanophenyl) 0.0-dimethyl phosphorothioate, 〇-(4-cyanophenyl)
0-Ethyl phenylphosphonothioate 1.0,0
-dimethyl 5-(N-methylcarbamoylmethyl)
Phosphorodithioney 1., 2-methoxy-411-1,
3,2-benzodioxaphosphorine-2-sulfide,
0.0-dimethyl 5-(t-ethoxycarbonyl-1
-phenylmethyl) phosphorodithioate and other organophosphorus insecticides, α-cyano-3-phenoxybenzyl 2-
(4-chlorophenyl)isovalerate, 3-phenoxybenzyl 2,2-dimethyl-8-(2,2-dichlorovinyl)cyclopropanecarboxylate, α-cyano-8-phenoxybenzyl 2,2-dimethyl-8-(2
It can be used in combination with pyrethroid insecticides such as , 2-dibromovinyl) cyclopropanecarboxylate, etc., and neither of them will increase the control effect of each agent alone, and furthermore, the combination is expected to have a phase-shaving effect. It is something that will be done.

Next, test examples and formulation examples will be given to further clarify the usefulness of the composition of the present invention as a disinfectant for agriculture and horticulture.

Test Example 1 Cucumber Powdery Mildew Control Efficacy 90-A plastic pot of Tani was filled with sandy loam, and cucumbers (variety: Sumo Half Day) were sown. This was cultivated at room temperature for 8 days to obtain cucumber seedlings with expanded cotyledons. A water-diluted solution of the test compound in the form of an emulsion or a wettable powder was sprayed on the foliage of the seedlings until a sufficient amount of droplets adhered to the leaf surface. After the chemical solution is air-dried, the seedlings are infected with cucumber powdery mildew fungus (Sphaerotheca fu).
A conidial suspension obtained by mixing drug-resistant bacteria and susceptible bacteria was inoculated by spraying.

The plants were placed in a greenhouse and cultivated for 18 days to develop the disease, and then the disease state was observed.

Disease-causing dust was calculated using the method described below.

That is, depending on the appearance of lesions on the investigated leaves, 0.0.5.1,
The dust was classified into an index of 2.4, and the disease-causing dust was calculated using the following formula.

0: No bacterial flora or lesions observed on the leaf surface.

0.5...596 1ifl of multiplication on the leaf surface
Bacterial flora or lesions are observed in ii.

l: 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...1li on the leaf surface over 5096 of the leaf area
Ii plexus or lesions are observed.

The control value was calculated using the following formula.

As a result, compounds (7), (9), (1
21, Qal, (14) (71) Izureka and compound f
A+, (river, (C)), (f)), tl>l, ipl,
(01, (When mixed with any of the rivers and sprayed, it was found that they were more effective in controlling staghorn V5 than when they were sprayed alone. 1, Table 2 Test Example 2 Tomato Gray Mold Control Effect 9 〇-A plastic bottle in the valley was filled with sandy loam soil, and tomatoes (product & in?lI8ju No. 2) were sown. These were cultivated in a greenhouse for 4 weeks to obtain tomato seedlings at the 4-leaf stage. Alternatively, a water-diluted solution of the test compound in the form of a wettable powder was sprayed on the stems and foliage at a rate of 10 per pot.After the chemical solution was air-dried, a mixture of drug-resistant and sensitive bacteria of Botrytis Clnerea was prepared. The conidial fluid was sprayed onto the conidia.

The specimens were left in a humid room at 20° C. for 5 days, and then the disease 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 8, compounds (9), 0(1), (
13), (14), or (15) and the compound (T
A superior pesticidal effect was obtained compared to when the mixture was sprayed with either of the following.

\,~ Table 8 i
296 powder is obtained.

Formulation Example 2 Wettable powder compound + 9120 parts, compound (Kl 10 parts, diatomaceous earth 4
By thoroughly grinding and mixing 5 parts of white carbon, 20 parts of white carbon, 8 parts of a wetting agent (sodium lauryl sulfate), and 2 parts of a dispersing agent (calcium lignin sulfonate), a wettable powder having a base ingredient content of 80% is obtained.

Formulation Example 8 Wettable powder compound (13Jl 0 parts, compound (1140 parts, diatomaceous earth 45 parts), /IN/II!l agent (calcium alkylbenzenesulfonate) 2.5 parts, and dispersant (calcium ligninsulfonate) 2. 5 parts were thoroughly pulverized and mixed to obtain a wettable powder with a main ingredient content of 50%.

43150 ) 7215-4
H (AOIN 47/20 43/78) 7215-4
H (A 01 N 47/20 37/32) 7419-
4HO Inventor: Kato Sube, 4-2-1 Takashi, Takarazuka City, Sumitomo Chemical Co., Ltd. 0 inventors: Hiroshi Noguchi, 4-2-1 Takashi, Takarazuka City, Sumitomo Chemical Co., Ltd., 0 inventors: Yukio Ishikuri Takarazuka 4-2-1 Ichitakashi, Sumitomo Chemical Co., Ltd. Author Shigeo Yamamoto 4-2-1 Takashi, Takarazuka City Sumitomo Chemical Co., Ltd. 0 author Katsuzo Kamoshita 4-2-1 Takashi, Takarazuka City No. Sumitomo Chemical Co., Ltd.

Claims (1)

[Claims] General formula [wherein, X represents a halogen atom or a methyl group]. Y represents a halogen atom, a methyl group, a lower alkoxyl group or a methoxymethyl group. 2 represents a hydrogen atom, a fluorine atom, or a lower alkoxyl group. A represents an oxygen atom or a sulfur atom. R represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group, or a lower alkyl group substituted with a substituent selected from among a lower alkoxyl group, a lower cycloalkyl group, a cya/44i, and a halogen atom. ] and one or more types of benzimidazole-based fungicides, thiophanate-based fungicides, or cyclic imide-based fungicides as active ingredients. A disinfectant composition for agricultural and horticultural use.