JPS58192806A - Agricultural and gardening fungicidal composition - Google Patents

Abstract

PURPOSE:An agricultural and gardening fungicidal composition having selective effect on chemical resistant microorganisms, obtained by blending an N-phenylcarbamate-based compound with one or more of a benzimidazole-based fungicide, a thiophanate-based fungicide, and a cyclic imide-based fungicide. CONSTITUTION:An agricultural and gardening fungicidal composition comprising one or more of N-phenylcarbamate-based compounds shown by the formula I (X and Y are alkyl, or alkoxy; R is alkyl, alkenyl, alkynyl, haloalkyl, etc.; Z is O or S) and one or more of a benzimidazole-based fungicide [e.g., methyl 1-(butylcarbamoylbenzimidazole-2-ylcarbamate, etc.], a thiophanate-based fungicide [e.g., 1,2-bis(3-methoxycarbonyl-2-thioureido)benzene, etc.] and a cyclic imide-based fungicide [e.g., N-(3', 5'-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-carboxyimide, etc.] as active ingredients.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a compound of the general formula [wherein X and Y are the same or different and represent a lower alkyl group or a lower furkyl group. R is a low M fulkyl group, a lower fulkenyl group, a lower fulkynyl group, a lower haloalkyl group,
It represents a lower alkyl group substituted with at least seven substituents selected from a lower haloalkyl group, a lower dirofurkyl group, a cyano group, a lower alkyl group, and a lower dichlorofurkyl group. 2 represents an oxygen atom or a sulfur atom. ] N-phenylcarbamenite compound represented by methyl/-(butylcarba□moyl)penzimidazole-coylcarbamate (hereinafter referred to as compound A,
2-(tertiazolyl)benzimidazole (hereinafter referred to as compound B) represented by the formula: methylbenzimidazo τ-ruylcarbamate represented by the formula (hereinafter referred to as compound C); Ru2
-(-monofuryl)benzimidazole (hereinafter referred to as compound), or thiophanate-based fungicides, such as -monofurylbenzimidazole (hereinafter referred to as compound), for example, -monofurylbenzimidazole (hereinafter referred to as compound), represented by the formula /, -bis(3-methoxyruponyl-thioureido)benzene (hereinafter referred to as compound) (arranged with E),
2-bis(3-ditricarbonyl-2-thiourido)benzene (hereinafter referred to as compound 1'), represented by the formula:

-/-(J'-methoxycarbonyl-'-thioureido)benzene (hereinafter referred to as compound G)
, formula phoryl7mino) +, / -(J'-methoxycarbonyl-2'-thioureido)benzene (hereinafter referred to as compound H), or a cyclic imide fungicide, such as kl -(J', j '-dichlorophenyl-/, cordimethyl, 'cyclopropane-/, 2-
Carpoxymido (hereinafter referred to as compound l), formula -/-
Isobrovir rubber moylimidazolidine, terdione (hereinafter referred to as compound J), formula -j-methyl-5-vinyloxazolidine-y-dione (hereinafter referred to as compound), formula dichlorophenyl) -j
-Methyl-, Gauge oxooxazolidine-5-carboxylate (hereinafter referred to as compound), etc.) A disinfectant composition for common use in farms, containing the above as active ingredients. It is.

Table 1.

Benzimidazole-based fungicides and thiophanate-based fungicides (hereinafter referred to as benzimidazole-thiophanate-based fungicides) have shown excellent control effects against pathogenic bacteria that parasitize agricultural and horticultural crops, and have been widely used since around 7'/7θ. It is widely used as a horticultural fungicide and has greatly contributed to increasing crop production. However, when these pesticides were continuously produced,
When sprayed on objects, drug resistance spreads, reducing the control effect of the drug and making it practically unusable.

If the expected pest control effect is not obtained even when spraying pesticides, and if the outbreak of disease cannot be suppressed, the damage to agricultural water and the users of the pesticides will be enormous.

Furthermore, benzimidazole Φ thiophanate film [11
It is known that those that are resistant to one of these fungicides are also resistant to other fungicides in this group, resulting in so-called cross-resistance. However, in fields where no pest control effect is observed, other benzimidazole/thiophanate-based RIs can be used. Even if one agent is sprayed,
No pest control effect can be expected. J1 of drug-resistant bacteria
In treated fields, the use of benzimidazole/thiophanate fungicides has to be discontinued, but there are many known cases in which the number of drug-resistant bacteria does not decrease even after discontinuing their use. Once the bacteria occurs, you will be affected by it for a long time. In addition, in such fields, target diseases can be controlled by spraying other fungicides that do not exhibit cross-resistance.
Very few benzimidazole-thiophanate fungicides exhibit excellent control effects, making accurate control difficult. The above-mentioned cyclic imide-based Mlli agent is effective against various plant diseases, especially gray mold, but it has the same problem of resistant bacteria as the benzimidazonyl thiophanate-based fungicide mentioned above. Considering the above-mentioned circumstances, they considered that if there is a fungicide that selectively kills drug-resistant bacteria, it can be expected to have a high disease control effect in fields where drug-resistant bacteria has developed. He worked hard on his invention. As a result, it was found that the aforementioned H-phenylcarbamate compound is a bactericidal agent that exhibits a strong bactericidal effect selectively against drug-resistant bacteria. As is clear from the test examples described later, the compound of the present invention is effective against diseases caused by resistant bacteria (hereinafter referred to as drug-susceptible bacteria) that are susceptible to benzimidazole-thiophanate fungicides or cyclic imide silkicides. Although it did not show any control effect, it showed an excellent control effect against diseases caused by drug-resistant bacteria, and the killing power of the compound of the present invention against drug-resistant bacteria was extremely selective.

However, in actual fields where pathogens are prevalent, drug-resistant bacteria and susceptible bacteria often coexist, and benzimidazole/thiophanate-based pesticides, cyclic imide threads, monocide, or the above-mentioned N-phenyl It is difficult to expect sufficient disease control effects by using any of the carbamate compounds alone. Therefore, we investigated the disease control effect of using a mixture of seven or more of these N-7-enyl carbamate compounds and a benzimidazole/thiophanate fungicide or a cyclic imide fungicide with /Wi or more. investigated. As a result, the disease control effect tends to be higher when N-phenylcarbamate-based compounds, benzimidazole-thiophanate-based fungicides, or cyclic imide-based 80M agents are used alone than when they are used in combination. It was done. Therefore, the agricultural fungicidal composition based on the compound of the present invention has high practical value as a fungicide that exhibits an excellent pest control effect in any field.

Furthermore, the fungicidal composition of the present invention can be used in fields where drug-resistant bacteria have not appeared, even when there is concern about the spread of drug-resistant bacteria due to continuous spraying of benzimidazole-thiophanate-based fungicides or cyclic imide-based fungicides. Its appearance can be prevented.

The agricultural and horticultural fungicidal composition of the present invention can be widely exposed.

The analogy is powdery mildew on ζ apples! (PcOxXOl-
・n1eoucotrxcha), black star disease @ (V@
nturia 1naequalis ), black spot disease @
(Jrcosphaeralln pomi), brown spot fungus (Marasonimmma'li), monilia disease fungus (8c'l*rotinia-man), oyster powdery mildew fungus (・Appendix 11aotinia 薗C0-), anthracnose carp (ciloeoaporium) m]ci) ,,
Botrytis cinersa on peaches, Botrytis cinersa on grapes, Botrytis cinersa on grapes,
Arooepora viticplm
), powdery mildew (Vncinulanecazor
), black rot fungus (l1sino@ampelina)
, late rot @ (Glomrel'la cingul)
ata), brown spot fungus of sugar beet <c@rcjapo
ra beticffim), beannut brown spot fungus (Oercoapora 'arachidico1m)
), Oercoaporspersomt
a), barley udon koji mold (machi 8uma-〇ρき已#
f, up, 'ho-sha), eye spot pathogen (
aercoapore1] Aherpotrichoi
a・8), Fusariuaichi wa1
), wheat powdery mildew fungus (Sukedo 1-gramini
a f, sp, tritici), cucumber udon disease @ (S voice■rotheaa fuligin
ea), Vine blight fungus (Myco pass-erallam)
elonis), Sclerotinia - (8clerotinia
sclerotiorum), botrytis blight (Bo
trytis cinerea), OjtacLogporium cucumerinum, and tomato leaf mold fungus (OjtacLogporiumfulv).
um ), Botrytia cine
rea', ), eggplant island blight fungus (Oorynagpo
ra mlongenae), strawberry udon and disease @
(8 to 71!Lerotheca hunmi)
, Flxsarlumoxysporum
f, sp, fragarias), onion gray rot fungus (Botrytis alli), lettuce sclerotium fungus (8cl*rotinia aclerot)
iorum), celery spot fungus (osraoaI
l! raapi1), Porus bean horn spot fungus (-o
imriopsi griseolA), Botrytis cin.raa of hops, Botrytis cin.raa.

Tobacco powdery mildew fungus (XrygipbBclchor)
acearum), rose scab* (Dipxoc
arpon rosae), tangerine scab fungus (E
lsime fawcetti), Blue mold fungus (P
enicilliumitalicum), green mold fungus (-Penicillium digitatum)
On the other hand, the fungicidal composition of the present invention is highly safe for humans, livestock, and fish, and has virtually no effect on agriculturally useful crops. It was also found that it can be used without causing any harm. Akira Honkaji fil1
When actually applying the composition, it can be used in pure form without adding other ingredients, or it can be mixed with a carrier to make it easier to use as a fungicide. 4*For example, powders, wettable powders, oils, emulsions, tablets, granules, microgranules, aerosols, flocs The above formulations generally contain active compounds (including mixed ingredients) of 0 to 95% by weight.
．． θ, preferably 10 to 50.0, usually /
It is appropriate to use an application amount of /θ to /θθ2 per θ arch. Since it varies depending on the type, application time, 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 ff1ll/ill, herbicides, plant growth regulators, insecticides, etc., such as 8-n-butyl-balata-butylbenzyldithiocarbonimidate, 0.0- Dimethyl 0-(J,6-dichloro-q-methylphenyl)suphorothioate, N-trichloromethylthiodes cyclohexene-7, codicarpoximide, cis-N
-(/,/,j,j-tetrachloroethylthio)-dercyclohexene-7.2-dicarboxyzincethylenebisdithiocarbamate, zinc dimethylthiocarbamate, manganese ethylenebisdithiocarbamate,
Bis(M,N-dimethylthiocarbamoyl), disulfide, tetrachloroisophthalonitrile, za-hydroxyquinoline, dodecylguanidine acetate, j, 6
-Syhydrocomethyl-/teroxathiin-3-
Kalxanilide, N'-dichlorofluoromethylthio-N, M-dimethyl-N'-phenylsulfamide, /
-C1l-chlorophenoxy)-3,3-dimethyl-/
-(/, j.

Fungicides such as &-triazol-/-yl)-nibutanone, methyl N-C2,4-dimethylphenyl)-N-methoxyacetyl-methylglycinate, aluminum A ethyl phosphite, 2,'I-dichlorophenoxyacetic acid , phenoxy herbicides such as comethyl-dachlorphenoxybutyric acid, comethyl-dachlorphenoxyacetic acid (including salts), -, dichlorophenyl da'-nitrophenyl ether, -.

ether, -1 chlorauder trifluoromethylphenyl 3'-ethoxy-q''-nitrophenyl ether,
dichlorophenyl q'-2) 1) -J'-
Diphenyl ether herbicides such as methoxylaenyl ether, -24t-dichloro7'enyl 3'-methoxycarbonyl-q'-nitrophenyl ether, cokechloruda, 6-pisethylamino/, 3.3-)su7dine , cochlorooguethyl 7 minnow 6-isobrobylamino/, J, j-triazine, comethylthiog,
6-pisethylamino/, 3. ! -Triazine, -1methylthioda, 6-pisisobrovir 7 minnow! ,3
．． J-) Triazine herbicides such as Su7jin, J-'(
J, 4t, dichlorophenyl) -t e' /-dimethylurea, 3-(3, goo dichlorophenyl) -/-
Methoxy-/-methylurea, / ("pα-dimethylpencyl)-J-p-)dilurea, /-(,2-
8 -(4I-chlorobenzyl)N,N
-diethylthiol carbamate, S-ethyl N, M-
Thiol carbamate herbicides of hexamethylenethiol carbamate group, 3. Gauge chlorpropionanilide, -1chloro-N-methoxymethyl-96'-diethylacetanilide, cochlorine, 2,4'-diethyl-N-(butoxymethyl)-7cetanilide, -
1 Loluco, 6'-diethyl 2N-(n-butoxymethyl)acetanilide, N-chlor 7cetyl-N-(
6-acid anilide herbicides such as λ,6-dinitylphenyl) glycine ethyl ester, uracil-based herbicides such as j-bromo-3-secondary-butyl-6-methyluracil 1,3-cyclohexyl-3,6-drimethyleneuracil Herbicides, /l/'-dimethylda, pyridinium salt herbicides such as 4I'-bipyridinium chloride, M (phosphonomethyl)glycine, N.

N-'bis(phosphonomethyl)glycine, 0-ethyl 0
-(-12-ditroj-methylphenyl)N-secondary-butyl sulforamide thioate, 5-(2-methyl-/-piperidylcarbonylmethyl)0,0-di-n-
Propyldithiophosphate, El-(,2-me,thyl-7-biveridylcarbonylmethyl)0,0-di-n-
Propyldithiophosphate, 8 (-2-methyl-
/-piperidylcarbonylmethyl)0.0-diphenyl ° Phosphorous herbicides such as dithiophosphate, toluidine herbicides such as α,α,α-trifluoro-1,6-sinitro-N, N-dipropyl-p-1 luidine , S-tert-butyl-J-(,2, dichloro-j-isopropoxyphenyl)-/, 3゜q-oxadiazolin-one, 3-isopropyl-
(/H)--s/, 3-benzothiadiazine-(3H)
-oney, -monodioxide, α-(β-naphthoxy)
Probionanilide, goo(,2,goo-dichlorobenzoyl)-/,3-dimethylpyrazol-y-yl p
-Toluenesulfonate, 3-(methoxycarbonylamino)phenyl 3-methylphenylcarbamate, dartumino-3-methyl-6-tzenyl/.

-, sheet triazine, o, o-dimethyl 0-(Q-nitro-3-methylphenyl) phosphorothioate, o-(
4-cyanophenyl)0゜0-dimethylphosphorothioate, O-(\-cyanophenyl)0-ethylphenylphosphonothioate, 0,0-dimethino νB-(N-methylcal''/<moylmethyl)phosphorodithioate,
Comethoxy 4 (H/eJs cobenzodioxaphosphorine-sulfide, 0.O-dimethyl 8-(/-
Ethoxycarbonyl-/-phenylmethyl) phosphorodithioate cape organophosphorus insecticide, a-cyano-3-phenoxybenzyl 2-(&-chlorofunyl)invalerate, 3-phenoxypenzylco, -1-dimethyl-j
-(,?,,2dichlorovinyl)cycloprotskidibenzyl-1-1dimethyl-J-(,!.

--It can be used in combination with pyrethroid insecticides such as dibromovinyl) cyclopropane carboxylate, without reducing the control effect of each of the four single agents,
Furthermore, a mutual effect due to mixing is also expected.

Next, test examples and formulation examples will be opened, and the Ikl of the composition of the present invention will be explained.
Further elucidating the usability of ikl's fungicide for use as an ornamental fungicide ◇ Test example / Effectiveness in controlling cucumber powdery mildew A plastic pot with a volume of θ1 was filled with gauzy soil, and cucumbers (variety: Sumo half-day) were sown. This was cultivated at room temperature for several 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 stems and leaves until a sufficient amount of droplets adhered to the leaf surface. After air drying, the seedlings were infected with cucumber powdery mildew @
A conidial suspension obtained by mixing drug-resistant and sensitive bacteria of S. uliginea was inoculated by spraying.

The plants were placed in a greenhouse and cultivated for /θ days to develop the disease, and then the disease state was observed and the 90 disease severity was calculated by the following method.

, that is, depending on the appearance of lesions on the investigated leaves, θ, θ, 3. /
, ko, and q, and the disease severity was calculated using the following formula.

(Onset M) (Onset M) θ・・・Bacteria on the leaf surface! Or no lesions are observed.

θ, S... Fungus lI or lesions are observed on the leaf surface in less than j- of the leaf area.

2--e Lesions of Sonosokiku are observed on the leaf surface in areas less than the leaf area.

Next, the control value was calculated using the following formula.

As a result, as shown in Table 1, compounds (da), ke), (7)
, V), (//) and the compound (A), (B)
, (0), (D), (I), (IF), (()), (H
) When sprayed in a mixture with any of the following, excellent control effects were observed when sprayed alone. A plastic pot with a volume of θ1 was filled with sandy loam soil, and tomatoes (variety: Fuku #-) were sown. This is warm pML,)
The tomato seedlings were cultivated for 4 weeks to obtain tomato seedlings at the leaf stage. For emulsion Maku, a water diluted solution of the test compound in the form of a wettable powder was sprayed on the foliage at a rate of 1/θ liter per pot. After the chemical solution was air-dried, a conidial liquid obtained by mixing drug-resistant and susceptible Botrytis cinsrea bacteria was spray inoculated.

This was kept in a humid room at -θ℃ for 1 day, 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/.

As a result, as shown in Table 3, the compounds (ge), (6), (?
), (/θ), (/-) and compound (I),
In the case of spraying together with either (J), (8)) or (L), a superior control effect was obtained compared to when they were sprayed alone. 0 Table 3 7 parts of compound (g), 7 parts of compound (J), clay trtr
By thoroughly pulverizing and mixing 10 s of talc and 10 s of talc, a powder having a base agent content of 2 t is obtained.

Formulation example - Wettable powder compound (10) - 0 parts, compound @) 70 parts, diatom ±qj
By thoroughly grinding and mixing 29 parts of white carbon, 3 parts of wetting agent (sodium lauryl sulfate), and part of dispersing agent (calcium lignin sulfonate), an irrigation agent with a base ingredient content of 3θ is obtained.0 Formulation Example 3 Water Compound (/, 2) 70 parts, Compound (z) yθ parts, diatom ±4 Ism, wetting agent (calcium alkylbenzenesulfonate) 2.5 parts and dispersing agent (lignin, calcium sulfonate) -0 parts If thoroughly crushed and mixed, an irrigation agent with a base ingredient content of 5 ots can be obtained. O Procedural amendment - letter (voluntary) 3 no ρ No. 1981 Shinroku A Day, Commissioner of the Patent Office Mr. Wakasugi Wainu/, Indication of the case 1988 Patent Whale No. 7176;! No.-0 Name of the invention lk Horticultural fungicidal composition 3, Relationship to the amended person's case Patent applicant address Kitahama-ri-chome/j, Higashi-ku, Osaka City Name (
Koθ? )Sumitomo Chemical Co., Ltd. Representative Sat
Person Mugu0 agent

Claims (1)

[Claims] General formula [wherein X and Y are the same or different and represent a lower fulkyl group, a ``lower fluorinyl group'' ◇ R is a lower fulkyl group, a lower fluoranyl group, a lower alkyl group 02 indicating a low M furkyl group substituted with at least seven tIt substituents among a lower haloalkyl group, a lower dirofurkyl group, a lower haloalkyl group, or a cyano group, a lower flukoxy group, and a lower dichlorofurkyl group. represents an acid group atom or a sulfur atom. ] N = phenyl carbamate Seven or more of the present compounds 111+ and a benzimidazole film [11, a thiophanate fungicide or a cyclic imide fungicide] are combined with a % hammer and -f.
h* Horticultural fungicidal composition.