DD296401A5 - FUNGICIDAL COMPOSITION - Google Patents

Abstract

The invention relates to a fungicidal composition for agriculture and horticulture, which comprises in addition to a Verduindenungsmittel a Traeger and / or a Adjuvan as the first active ingredient at least one amide derivative of the following general formula (I), wherein the substituents have the meaning given in the description, and as the second active ingredient, at least one component selected from acylalanine fungicides having control activity with respect to plant diseases caused by oomycetes, dithiocarbamate fungicides, N-haloalkylthioimio-fungicides, inorganic copper fungicides, tetrachloroisophthalonitrile, dichlofluanid and fluazinam. Formula (I) {Fungicidal Compositions; Agriculture; Horticulture; active ingredient; amide derivative}

Description

Field of application of the invention

The present invention relates to a fungicidal composition for agriculture and horticulture, which comprises as the first active ingredient at least one amide derivative of the following general formula (I)

(I)

wherein one of X and Y represents a sulfur atom and the other represents a carbon atom, Z represents a nitrile or thioamide group, each of R ¹ and R ^{2 represents} a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, a Halomethyl group or a phenyl group and R ^{3 is} an alkenyl group having 2 to 6 carbon atoms, a haloalkenyl group having 2 to 4 carbon atoms, a furyl group, a thienyl group, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, an alkinyloxy group having 3 to 5 carbon atoms, an alkynylthio group having 3 to 5 carbon atoms, a pyrazolyl group or an unsubstituted or halo-substituted phenyl group; and at least one component selected from acylalanine fungicides having control of oomycete-induced plant diseases, dithiocarbamate fungicides, N-haloalkylthioimide fungicides, inorganic copper fungicides, tetrachloroisophthalonitrile, dichlorofluidide and fluazinam.

Characteristic of the known state of the art

Heretofore compounds having different chemical structures have been used as fungicides for agriculture and horticulture and contributed greatly to the control of plant diseases and, consequently, to the development of agriculture. However, these conventional fungicidal chemicals proved insufficient in their controlling activity and safety. For example, some dithiocarbamate fungicides such as zinc ethylene bis (dithiocarbamate) [zineb], manganese ethylene bis (dithiocarbamate) [maneb], a complex of manganese ethylene bis (dithiocarbamate) and zinc ethylene bis (dithiocarbamate) [Mancozeb ] and Dizink-bis-dimethyldithiocarbamate J-ethylene-bis-ldithiocarbamate) [polycarbamates], N-haloalkylthioimide fungicides, such as N-trichloromethylthio-cyclohexene-1-dicarboximide [captan], N-i'.i ' '-Tetrachloroethylthio ^ -cyclohexene-i-dicarboximide [captofol] and N-trichloromethylthiophthalimide [folpet], inorganic copper fungicides such as cuprisulfate, basic cuprisulfate, basic cupric chloride and cupric hydroxide, tetrachloroisophthalonitrile [TPN], N- (dichlorofluoromethylthio) -N ', N-dimethyl-N-phenylsulfamide [Dichlofluanide I and S-chloro-N-f S -chloro-S-trifluoromethyl-pyridyl-D-e-dinitro-trifluoromethylaniline [fluazinam], an excellent controlling efficacy for diseases in plants such as fruit trees and vegetables, and are widely used as F used for agriculture and horticulture. However, these chemicals are predominantly preventive and are not expected to have a healing effect. Therefore, they have the serious shortcoming that when observing the occurrence of plant diseases, one can not expect sufficient efficacy from these chemicals. Considering, in a given situation, the use of chemicals to control plant diseases, these chemicals are sprayed more or less after the onset of symptoms of the plant disease and the above chemicals are difficult for complete control of the diseases. Furthermore, the concentrations of these chemicals in which they have a controlling effect are very high so that they are safe to use with difficulty, and some of these chemicals have a non-negligible toxicity to fish.

To remedy these shortcomings, extensive research has been carried out with regard to new means of control. For example, acylalanine fungicides such as N- (2,6-dimethylphenyl) -N- (2'-methoxyacetyl) alanine methyl ester [metalaxyl], N- (2,6-dimethylphenyl) -N- (2-furoyl) alanine methyl ester [furalaxyl], N- (2,6-dimethylphenyl) -N- (phenylacetyl) alanine methyl ester [benalaxyl], 2-chloro-N- (2,6-dimethylphenyl) -N- (tetrahydroxy) 2-oxo-3-furanyl) acetamide [Ofurace] and 2-methoxy-N- (2,6-dimethylphenyl) -N- (2-oxo-1,3-oxazolidin-3-yl) -acetamide [oxadixyl] , developed as a means to control plant diseases caused by Oomycetes, which also have excellent healing properties and have been put into practical use worldwide. It has already been stated that these chemicals were resistant to strains and their control effect consequently decreased.

Numerous active benzylamide compounds have been found and used as herbicides or fungicides. For example, known substituted benzamide derivatives include ethyl N-benzoyl-N- (3,4-dichlorophenyl) -2-amino-propionate [benzoylpropyl] ethyl as a herbicide and N- (3-isopropoxyphenyl) -2-methylbenzamide [mepronil] as a fungicide.

BP-2094786, BP-2095237 and BP-2107308 disclose a herbicide and a fungicide comprising a substituted benzylamide derivative having a 4-pyridylcarbonyl, 2-furylcarbonyl, 2-thienylcarbonyl or 2-benzofurylcarbonyl group, but its phytotoxicity compared to crops is a problem.

Object of the invention

The aim of the invention is to provide a fungicidal composition for agriculture and horticulture, which contains the compound as the first active ingredient and a specific, known, fungicidal compound as a second active ingredient.

Explanation of the essence of the invention

It has been found that amide derivatives having a thiazole or isothiazole ring have a biological activity which was by no means unpredictable due to the compounds mentioned above by way of example, and an excellent control activity against a wide range of plant diseases; and in particular that these amide derivatives have both a preventive and a healing effect in controlling various crop diseases such as late blight and powdery mildew.

The amide derivatives used in the present invention have the following general formula (I)

COMHCH

wherein one of X and Y represents a sulfur atom and the other represents a carbon atom, Z represents a nitrile or thioamide group, each of R ¹ and R ^{2 represents} a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, a halomethyl group or a phenyl group and R ^{3 is} an alkenyl group having 2 to 6 carbon atoms, a haloalkenyl group having 2 to 4 carbon atoms, a furyl group, a thienyl group, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, an alkynyloxy group having 3 to 5 carbon atoms, an alkynylthio group having 3 to 5 carbon atoms, a pyrazolyl group or an unsubstituted or halo-substituted phenyl group

In the amide derivatives of the general formula (I), examples of the alkyl group of R ¹ and R ^{2 are} methyl, ethyl, n-propyl, isopropyl, η-butyl, isobutyl, sele-butyl, tert. Butyl, n-pentyl and n-hexyl groups. Examples of the halomethyl group are chloromethyl and trifluoromethyl groups. The alkenyl group of R ³ is, for example, a vinyl, allyl, propen-1-yl, 2-methylpropen-1-yl, i-methyl-propen-1-yl, 1,2-dimethylpropen-i-yl, 2-ethylpropen-1-yl or 2-n-propylpropen-i-yl group. The haloalkenyl group is z. As a 2-chloroethenyl, 2-chloropropene-1 -yl or 1-methyl-2-chloropropene-i -yl group. Examples of the alkoxy group are methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy and tert-butoxy groups. Examples of the alkylthio group are methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio and tert-butylthio groups. Examples of the AHdnyloxygruppe are propin-2-yloxy, 3-methylpropin-2-yl-oxy and 3-ethylpropin-2-yloxy groups. Examples of the alkynylthio groups are propin-2-ylthio, 3-methyl-2-yl-thio, S-ethyl-propyl-3-thio groups. The halogen atom may be, for example, fluorine, chlorine, bromine or iodine. The compounds of general formula (I) are new.

The amide derivatives used in the present invention can be prepared by the following Reaction Schemes (a) to (c). Reaction scheme (a)

CN

(Ii) Reactive Deri- (III)

especially from this

I ₍ \ 7t о J и. Ι ^ · 1

(IV)

In this scheme, the amide derivatives of the general formula (IV) can be prepared by reacting the heterocyclic, 5-membered carboxylic acid of the general formula (II) or its reactive derivative (such as an acid chloride or an acid anhydride) with the aminoacetonitrile of the general formula (III) or whose salt is converted. Various methods are available for carrying out the reaction according to scheme (a) and are described below with reference to the following reaction schemes (a) -1 to (a) -5.

Reaction scheme (a) -1

A process comprising converting the carboxylic acid to a chloride and reacting it with aminoacetonitrile:

SOCl.

N? з ν '  г ^{: 0} 2 ^H ч ⁽ Il ;) ^H 2 N- cn: ^ CN < Ill)

(IV)

Usually, the carboxylic acid derivative (II) is heated in an excess of thionyl chloride. After the reaction, excess thionyl chloride is evaporated off to obtain the acid chloride. Sometimes the reaction in thionyl chloride does not go well. In such a case, the carboxylic acid (II) is treated with an almost weight equivalent amount of phosphorus pentachloride in an inert solvent. This makes the reaction smooth. After the reaction, low boiling materials are evaporated to give the acid chloride. The resulting acid chloride is reacted in an inert solvent with the aminoacetonitrile (III) or its salt in the presence of a weight-equivalent amount or a slight excess of a base to easily give the amide derivative (IV). If the salt of the aminoacetonitrile is used, the base is additionally fed in an amount which is necessary for the neutralization of the salt. The inert solvent is inert to the chloride and the aminoacetonitrile. Specific examples are ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran and dioxane, hydrocarbons such as benzene, toluene, xylene and ligroin, halogenated hydrocarbons such as dichloromethane, chloroform and carbon tetrachloride, esters such as ethyl acetate and ethyl propionate, and aprotic polar solvents such as N , N-dimethylformamide, dimethyl sulfoxide and 1,3-dimethylimidazolidinone. Pyridine can be used as the base and solvent. Examples of the base may be organic bases such as triethylamine, dimethylaniline, pyridine and DBU, and inorganic bases such as ammonia, potassium hydrogencarbonate, potassium carbonate, sodium carbonate, sodium hydrogencarbonate, sodium hydroxide and ammonium carbonate, although these examples are not restrictive. It is undesirable to carry out this reaction at too high a temperature because the thermal stability of the aminoacetonitrile derivative intermediate (III) is low. Preferred reaction temperatures are 10 to 50 ^° C. After the dropwise addition of the aminoacetonitrile derivative (III), the mixture is continuously stirred at room temperature to complete the reaction. The reaction time, which varies depending on the reaction temperature, is usually 0.5 to 4 hours. After the reaction, the crude reaction product is obtained by a conventional method. The resulting desired amide derivative can be easily isolated and purified by a conventional method such as recrystallization or column chromatography.

Reaction scheme (a) -2

A process comprising reacting an anhydride of the carboxylic acid with the aminoacetonitrile.

(II)

CN

HN-CN

(III)

CN

ONHC н;

(IV)

The amide derivative (IV) can be obtained by carrying out the same reaction as in Reaction Scheme (a) -1 except that the acid anhydride is used in place of the acid chloride.

Reaction scheme (a) -3

A process comprising reacting a mixed acid anhydride of the carboxylic acid with the aminoacetonitrile.

N (II)

O ₂ H

ClCO ₂ R

-C-O-C-OR

CN

(III)

CN

ONHCH;

(IV)

(In the above scheme, R ^{4 is} a lower alkyl group.)

The carboxylic acid derivative (II) is dissolved in an organic solvent, and in the presence of a base, a chloroformate ester is added to form a mixed acid anhydride. Addition of the aminoacetonitrile (III) to the mixed acid anhydride gives the amide derivative (IV). The organic solvent and the base may be the same as in the reaction scheme (a) -1. The reaction temperature is -50 to +20 ⁰ C, preferably -10 to + 10 ° C, for the reaction of the carboxylic acid with chloroformate and 0 to 50 ° C, preferably 10 to 30 ⁰ C, for the reaction of the mixed anhydride with the aminoacetonitrile , The isolation and purification of the final product can be easily done according to a conventional method, as in the case of reaction scheme (a) -1.

Reaction scheme (a) -4

Process comprising the use of carbonyldiimidazole (CDI).

N-C-N

(CDI)

.CN

(III)

CN

onhch;

(IV)

The carboxylic acid derivative (II) is dissolved in an organic solvent and carbonyldiimidazole is added. This is followed at 0 to 50 ° C, preferably 0 to 30 ⁰ C, the addition of aminoacetonitrile (III) to give the amide derivative (IV). The organic solvent used may be the same as that used in the reaction of Reaction Scheme (a) -1. The isolation and purification of the final product can be conveniently accomplished in a conventional manner in the same manner as described for the reaction in Reaction Scheme (a) -1.

Reaction scheme (a) -5 Process comprising the use of dicyclohexylcarbodiimide (DCC).

N (II)

Q-N = C = N-Q

° 2 ^H

(DCC)

-CO-O-C

NH

H ₂ N-CN

 (III)

CN 3

ONHCH;

(IV)

The carboxylic acid derivative III) is dissolved in an organic solvent and dicyclohexylcarbodiimide is added to the solution

added. While cooling the solution with ice-water, the aminoacetonitrile (III) is added to obtain the amide derivative. The organic solvent used in this reaction may be the same as those exemplified in the reaction scheme (a) -1. The isolation and purification of the final product can be easily accomplished by a conventional method.

In addition to the reactions shown in Reaction Schemes (a) -1 to (a) -S, for the preparation of the amide derivatives Methods are used, as they are commonly used in the field of peptide synthesis. If R ³ in the general formula (IV) is an alkoxy, alkylthio, alkynyloxy, alkynylthio or pyrazolyl group, this can be Amide derivative (IV) can be prepared according to the following method (b). Reaction scheme (b)

(V)

ri unc allyl acetate in Löbungsir.it tel

R ¹

: uiihc.i.cn

(VI)

HrT (VII)

Tribthylar. in

(IV)

An N-cyanomethylcarboxyamide (V) corresponding to the formula (TV) in which R ^{3 is} a hydrogen atom is a synthesis intermediate for a compound of the general formula (IV) in which R ^{3 is} an alkyl oxy, alkylthio, Af kinyloxy-, Alkfnylthio- or pyrazolyl group, very important.

Treatment of the N-cyanomethylcarboxyamide (V) with a halogenating agent in a suitable solvent gives a halogenated intermediate (VI). Bromine or N-bromosuccinimide can be used as halogenating agent. Examples of solvents are aliphatic halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride and 1,4-dichloroethane, and aliphatic carboxylic acid esters such as methyl acetate, ethyl acetate, isopropyl acetate and ethyl propionate. The reaction temperature is 30 to 80 ^° C., preferably 30 to 50 ° C. This reaction can be carried out in an inert gas atmosphere Since the halogenation intermediate (VI) is unstable, it is immediately reacted with HR ³ (VII) Examples of the acid acceptor are tertiary amines such as triethylamine and dimethylaniline, although they are not limitative It is desirable that this reaction be carried out in a solvent or diluent It is desirable to have high temperatures in carrying out this reaction It is desirably carried out under cooling because it is exothermic, The desired amide derivative (IV) can be purified in a conventional manner by recrystallization, column chromatography, etc., as the thermal stability of the intermediate is low.

A compound of the formula (VIII) corresponding to a compound (1) in which Z represents a thioamide group can be prepared by the following method (c).

Reaction scheme (c)

а ¹ У

см .. /

-C ^r üAC'A

(IV) (VIII)

The thioamide derivative (VIII) can be obtained by reacting the compound (IV) with gaseous hydrogen sulfide in the presence of a catalytically effective amount of a tertiary amine in an inert solvent, e.g. Aliphatic, halogenated hydrocarbons, such as dichloromethane, chloroform, carbon tetrachloride, and 1,4-dichloroethane, or aliphatic carboxylic acid esters, such as methyl acetate, ethyl acetate, isopropyl acetate, and ethyl propionate. The isolation and purification of the desired product can be easily carried out in a conventional manner by recrystallization, column chromatography, etc.

The invention relates to a fungicidal composition for agriculture and horticulture which comprises a diluent or a carrier and / or an adjuvant and as the first active ingredient at least one amide derivative of the following general formula (I):

wherein one of X and Y represents a sulfur atom and the other represents a carbon atom, Z represents a nitrite or thioamide group, each of R ¹ and R ^{2 represents} a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, a halomethyl group or a Phenyl group and R ^{3 is} an alkenyl group having 2 to 6 carbon atoms, a haloalkenyl group having 2 to 4 carbon atoms, a fury group, a thienyl group, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, an alkinyloxy group having 3 to 5 carbon atoms, an alkynylthio group having 3 to 5 carbon atoms, a pyrazolyl group or an unsubstituted or halo-substituted phenyl group, and as the second active ingredient at least one component selected from acylalanine fungicides having activity in control of plant diseases caused by oomycetes, dithiocarbamate Fungicides, the N-haloa alkylthioimide fungicides, inorganic copper fungicides, tetrachloroisophthalonitrile, dichlofluanid and fluazinam.

With regard to the second active ingredient used in the invention, examples of acylalanine fungicides are metalaxyl, furalaxyl, benalaxyl, ofurace, oxadixyl and cyprofuram. Examples of dithiocarbamate fungicides are zineb, maneb, mancozeb, polycarbomates and propineb.

Captan, Captafol and Folpet are examples of the N-halo-octyl-thioimide fungicides. Examples of the inorganic copper fungicides are cuprisulfate, basic cuprisulfate, basic cupric chloride and cupric hydroxide.

The newly prepared prepared compound has both preventive and healing effects against a wide range of diseases in fruit trees and vegetables, and exhibits an excellent control effect against those plant diseases in which pathogenic fungi have acquired resistance to conventional fungicidal chemicals. Furthermore, the composition according to the invention has a sufficiently long residual action and has no phytotoxicity. It also has extremely low toxicity to warm-blooded animals and fish. As a fungicide for agriculture and horticulture, the composition according to the invention has a controlling effect on a wide range of plant diseases. Examples of plant diseases to which the composition of the present invention shows an excellent control effect include frost rot (Glomerella cingulata), anthracnose (Elsinoe ampelina), powdery mildew (Uncinula necator). Rust or fire (Phacospora ampelopsidis) and downy mildew (Plasmopara viticola) of the grape; Rust or fire (Gymnosporangium yamadae), Alternaria leaf spot (Alternaria mali), fruit spots (Mycosphaerella pomi), scab (Venturia inaequalis) and powdery mildew (Podopsphaera

leucotricha) of the apple, anthracnose (Colletotrichum lagenanum), powdery mildew (Sphaerotheca fuligmea), rubbery stem rot (Mycosphaerella meloms), downy mildew (Pseudoperonospora cubensis), Phytophthora rotten (Phythophthora melonis), scab (Cladosporium cucumerinum) and bacterial spots (Pseudomonas lachrymans) for pumpkin, early rotten or mildew (Alternaria solani), leaf mold (Cladosporium fulvum), Phytophthora rotten (Phytophthora capsici), herbaceous rot (Phytophthora infestans) and powdery mildew (Erysiphe cichoracearum) in tomato, Alternana leaf spot (Alternaria japonica), white Spots (Cercosporella brassicae) and powdery mildew in cruciferous glands, rust (Puccinia aiii) and downy mildew (Peronospora destructor) of green onion, downy mildew (Peronospora spinaciae) in spinach, scab (Elsinoe glycines), purple spots (Cercospora kikuchii) and fake Mildew (Peronospora manshurica) of soybean, anthracnose (Colletotrichum hndem uthianum) and rust (Uromnyces appendiculatus) of the white bean, downy mildew (Peronospora viciae) in field beans, black rot (Phytophthora nicotiana var nictiana) of tobacco, mature (Alternana solani) and cabbage stover (Phytophthora infestans) in potato, downy mildew (Pseudoperonospora humuli) in hops, Phytophthora rotten (Phytophthora cinnamomi) in pineapple, Phytophthora rotten pepper (Phythophthora capsici), powdery mildew (Sphaerotheca humuli) and red rot (Phytophtora fragane) of strawberry, and gray mold (Botrytis cinerea), Sclerotinis Disease (Sclerotima sclerotiorum) and putrefaction or Umfallskrankheit (by Phythium etc) of various crops

The compounds described are applied by seed pickling, foliar spraying, soil treatment, etc. The compounds exhibit sufficient effectiveness when applied by methods commonly used by those skilled in the art. The rate of application of the compounds and the concentrations at which they are applied may depend on the crop and the disease to be treated, extent of onset of the disease, formulation of the compound, method of application and various environmental conditions When sprayed on, the appropriate amount of compound as the active ingredient is 50 to 5000 g / ha. preferably 100 to 2000 g / ha If it is to be sprayed as a wettable powder or as an emulsifiable concentrate diluted with water, the Verdunnungsverhaltnis preferably 200 to 10,000, preferably 500 to 5000 The inventive fungicidal composition for agriculture and horticulture can, together with Other agricultural chemicals may be used or formulated as another fungicide, insecticide or plant growth regulator, soil conditioning agent or fertilizer substance. The described compounds may be applied as such, but preferably in the form of a composition with a carrier (including solid or inorganic) liquid diluents fall). The carrier used herein means a synthetic or natural, inorganic or organic substance which is incorporated to assist in the contact of the active ingredients at the site to be treated and to facilitate the storage, transport and handling of the compound as an active ingredient

Suitable solid carriers and liquid carriers as well as adjuvants may be the same as those exemplified above

Usually, the amount of the active ingredients in the composition of the present invention is 0.5 to 20% by weight for a dust, 5 to 20% by weight for an emulsifiable concentrate, 10 to 90% by weight for a wettable powder, 0.1 to 20% by weight for granules and 10 to 90% by weight of a flowable agent The amount of the carrier in the formulation is usually 50 to 99% by weight for a dust, 60 to 95% by weight for an emulsifiable concentrate, 10 to 90% by weight for a wettable powder, 80 to 99% by weight % of granules and 10 to 90% by weight of a flowable agent The amount of adjuvant is usually 0.1 to 20% by weight for a dust, 1 to 20% by weight for an emulsifiable concentrate, 0.1 to 20% by weight for a wettable powder, 0.1 to 20 wt% for granules and 0.1 to 20 wt% for a flowable agent The ratio of the fungicide as the second active ingredient to the amide derivative of the invention can be freely varied between 0.1 and 30

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The following formulation examples illustrate the preparation of the inventive fungicidal composition for agriculture and horticulture The active compound is represented by the compound numbers given in Table 1 All parts are by weight

Formulation Example 1 Dust

3 parts of compound No. 5, 20 parts of diatomaceous earth, 30 parts of terra alba and 47 parts of talc were pulverized and mixed uniformly to give 100 parts of dust

Formulation Example 2 Wettable powder

Thirty parts of Compound No. 19.47 parts of diatomaceous earth, 20 parts of terra alba, 1 part of sodium lignosulfonate and 2 parts of sodium alkylbenzenesulfonate were uniformly pulverized and mixed to give 100 parts of a wettable powder

Formulation Example 3 Emulsifiable concentrate

20 parts of Compound No. 6.10 parts of cyclohexane, 5 mol% of xylene and 20 parts of Sorpol (Trade name of Toho Chemical Co., Ltd. (surfactant) were uniformly blended to give 100 parts of an emulsifiable concentrate

Formulation Example 4 Granules

1 part of Compound No. 2.78 parts of bentonite, 20 parts of talc and 1 part of sodium lignosulfonate were mixed and added with a moderate amount of water, and the mixture was kneaded. The kneaded mixture was granulated by a conventional method in an extrusion granulation machine and dried To give 100 parts of granules

Formulation Example 5 Granules

5 parts of Compound No. 11.1 parts of polyethylene glycol nonylphenyl ether, 3 parts of polyvinyl alcohol and 91 parts of clay were uniformly mixed. Water was added, and the mixture was granulated and dried to obtain 100 parts of granules

Formulation Example 6 Dust

2 parts of Compound No. 20.40 parts of calcium carbonate and 58 parts of clay were uniformly mixed to give 100 parts of dust

Formulation Example 7 Wettable powder

50 parts of Compound No. 37.40 parts of talc, 5 parts of sodium lauryl phosphate and 5 parts of sodium alkylnaphthalenesulfonate were mixed to give 100 parts of wettable powder

Formulation Example 8 Wettable powder

50 parts of compound No. 4.10 parts of sodium lignosulfonate, 5 parts of sodium alkylnaphthalenesulfonate, 10 parts of white carbon and 25 parts of diatomaceous earth were mixed and pulverized to give 100 parts of wettable powder

Formulation Example 9 Flowable agent

40 parts of Compound No. 10.3 parts of carboxymethyl cellulose, 2 parts of sodium lignosulfonate, 1 part of dioctylsulfosuccinate sodium salt and 54 TeMe of water were wet-pulverized by a sand grinder to give 100 parts of a flowable agent

Formulation Example 10 Dust

2 parts of compound No. 2.2 parts of metalaxyl, 20 parts of diatomaceous earth, 30 parts of terra alba and 45 parts of talc were mixed and pulverized to give 100 parts of dust

Formulation Example 11 Wettable powder

Fifteen parts of compound No. 4.15 parts of oxadixyl, 47 parts of diatomaceous earth, 20 parts of terra alba, 1 part of sodium lignosulfonate and 2 parts of sodium alkylbenzenesulfonate were uniformly pulverized and mixed to give 100 parts of wettable powder

Formulation Example 12 Wettable Powder 10 parts of compound No. 6.20 parts of metalaxyl, 55 parts of MeMeTaIc, 3 parts of sodium lauryl phosphate and 2 parts of sodium alkylnaphthalenesulfonate were mixed to give 100 wt. Of wettable powder

Formulation Example 13 Wettable Powder

5 parts of Compound No. 2.15 parts ofurace, 65 parts of diatomaceous earth, 10 parts of white carbon, 3 parts of sodium lauryl phosphate and 2 parts of sodium alkylnaphthalenesulfonate were mixed to give 100 wt. Of wettable powder

Formulation Example 14 Wettable powder

20 parts of Compound No. 2, 30 parts of benalaxyl, 35 parts of talc, 10 parts of white carbon, 3 parts of sodium lauryl phosphate and 2 parts of alkylnapthalene sulfonate were mixed to give 100 parts of wettable powder.

Formulation Example 15 Emulsifiable concentrate

7 parts of Compound No. 6.10 parts of metalaxyl, 50 parts of phenoxyethanol, 28 parts of xylene, 3 parts of polyoxyethylene styrylphenyl ether and 2 parts of sodium alkylnaphthalenesulfonate were mixed to give 100 parts of emulsifiable concentrate.

Formulation Example 16 Granules

3 parts of compound No. 17.10 parts of metalaxyl, 84 parts of clay, 1 part of polyethylene glycol nonylphenyl ether and 2 parts of polyvinyl alcohol were uniformly mixed and kneaded by adding a moderate amount of water. The kneaded mixture was granulated by a conventional method using an extrusion granulator and dried to give 100 parts of granules.

Formulation Example 17 Wettable powder

5 parts of compound No. 4.45 parts of mancozeb, 27 parts of diatomaceous earth, 20 parts of terra alba, 1 part of sodium lignosulfonate and 2 parts of sodium alkylbenzenesulfonate were pulverized and mixed uniformly to give 100 parts of wettable powder.

Formulation Example 18 Wettable powder

10 parts of compound No. 18, 50 parts of mancozeb, 35 parts of talc, 3 parts of sodium lauryl phosphate and 2 parts of sodium alkylnaphthalenesulfonate were uniformly pulverized and mixed to give 100 parts of wettable powder.

Formulation Example 19 Wettable Powder

5 parts of compound No. 2, 50 parts of captan, 40 parts of talc, 3 parts of sodium lauryl phosphate and 2 parts of sodium alkylnaphthalenesulfonate were uniformly pulverized and mixed to give 100 parts of wettable powder.

Formulation Example 20 Wettable powder

Ten parts of compound No. 2, 50 parts of captafol, 35 parts of talc, 3 parts of sodium lauryl phosphate and 2 parts of sodium alkylnaphthalenesulfonate were uniformly pulverized and mixed to give 100 parts of wettable powder.

Formulation Example 21 Wettable Powder

5 parts of Compound No. 6, 50 parts of Folpet, 40 parts of talc, 3 parts of sodium lauryl phosphate and 2 parts of sodium alkylnaphthalenesulfonate were uniformly pulverized and mixed to give a wettable powder.

Formulation Example 22 Wettable powder

5 parts of Compound No. 4, 50 parts of basic copper chloride, 40 parts of talc, 3 parts of sodium lauryl phosphate and 2 parts of sodium alkylnaphthalenesulfonate were uniformly pulverized and mixed to give 100 parts of wettable powder.

Formulation Example 23 Wettable powder

7 parts of compound No. 4.50 parts of basic copper sulfate, 38 parts of talc, 3 parts of sodium lauryl phosphate and 2 parts of sodium alkylnaphthalenesulfonate were uniformly pulverized and mixed to give 100 parts of wettable powder.

Formulation Example 24 Wettable powder

5 parts of Compound No. 6, 50 parts of TPN, 40 parts of talc, 3 parts of sodium lauryl phosphate and 2 parts of sodium alkylnaphthalenesulfonate were uniformly pulverized and mixed to give 100 parts of wettable powder.

Formulation Example 25 Wettable powder

7 parts of compound No. 2.50 parts of zineb, 3 parts of sodium lignosulfonate, 3 parts of sodium alkylnaphthalenesulfonate, 7 parts of white carbon and 30 parts of diatomaceous earth were uniformly pulverized and mixed to give 100 parts of usable powder.

Formulation Example 26 Wettable powder

3 parts of Compound No. 2, 50 parts of mancozeb, 3 parts of sodium lignosulfonate, 3 parts of sodium alkylnaphthalenesulfonate, 5 parts of white carbon, 16 parts of terra alba and 20 parts of diatomaceous earth were uniformly pulverized and mixed to give 100 parts of wettable powder.

Formulation Example 27 Wettable powder

5 parts of Compound No. 10, 50 parts of dichlofulanide, 40 parts of talc, 3 parts of sodium lauryl phosphate and 2 parts of sodium naphthalene sulfonate were uniformly pulverized and mixed to give 100 parts of wettable powder

Formulation Example 28 Granules

1 part of Compound No. 2.2 parts of polycarbamate, 85 parts of clay, 9 parts of diatomaceous earth, 1 part of polyethylene glycol nonylphenyl ether and 2 parts of polyvinyl alcohol were uniformly mixed and further kneaded by adding a moderate amount of water. The kneaded mixture was granulated in an extrusion granulator by a conventional method dried to give 100 parts of granules

Formulation Example 29 Dust

2 parts of compound No. 4.20 parts of polycarbamate, 10 parts of diatomaceous earth, 20 parts of terra alba and 48 parts of talc were uniformly pulverized and mixed to give 100 parts of dust

The following test examples illustrate the efficacy of the compounds prepared as a fungicide for agriculture and horticulture and the fungicidal composition for agriculture and horticulture. The compounds used in these test examples are characterized by the numbers shown in Table 1 or the symbols in Table 2

Table 2

A complex of manganese and zinc ethylene-bis-dithiocarbamatenl / Mancozeb /

B tin ethylene-bis-dithiocarbamate) / zineb /

C N-T V ^ '^' - Tetrachloroethylthio ^ -cyclohexene-i ^ -dicarboximide / captafol /

D basic copper chloride

E tetrachlorophthalonitrile / TPN /

F 3-chloro-N- (3-chloro-5-trifluoromethyl-2-pyndyl) -2,6-dinitro-4-trifluoromethylaniline / cichlofulanide /

G N- (2,6-dimethylphenyl) -N- (2'-methoxyacetyl) alanine methyl ester / metalaxyl /

H N- (2,6-dimethylphenyl) -N- (2-furoyl) alanine methyl ester / furalaxyl /

I N- (2,6-dimethylphenyl) -N- (phenylacetyl) alanine methyl ester / benalaxyl /

J 2-Chloro-N- (2,6-dimethylphenyl) -N- (tetrahydro-2-oxo-3-furanyl) -acetamide / Ofurace /

K 2-Metoxy-N- (2,6-dimethylphenyl) -N- (2-oxo-1,3-oxazolidin-3-yl) -acetamide / oxadixyl

L 3-chloro-N- (oxoperhydro-3-furyl) -cyclopropanecarboxyanihd / cyprofuram /

M N- (a-cyanofurfuryl) -2,6-dichlorophenyl-4-carboxamide

N, N- (a-cyanofurfuryl) furan-2-carboxamide

annotation

Compounds M and N are described in the above-mentioned, published British Patent Application BP-2095237. Compounds G to L are commercially available agricultural chemicals for controlling potato herb rot and cucumber downy mildew

Test Example 1 Test for control of potato rape (preventive effect)

A chemical (obtained by preparing a wettable powder of each test compound according to the method of Formulation Example 8 and diluting it with water to a predetermined concentration) was applied to potatoes (variety "Danshaku", plant height about 25 cm) grown in pots in my greenhouse a rate of 50ml /

3 pots applied using a spray gun (1.0kg / cm ² ) and then air dried. A zoospore suspension of Phytophthora infestans cultured on a potato disk for 7 days was sprayed and inoculated on the potato plant. The test plant was allowed to grow for 6 days a temperature of 17 to 19 ° C and a humidity of more than 95%, and then examined the extent of the formation of damage For each of the Blatter observed and evaluated the proportion of the area of damage and determined the index of the extent of the disease ( Disease index) For each of the test areas, the damage index was calculated according to the following equation

_o , 4n ₄ + 3n ₃ + 2n ₂ + 1n, + On ₀ peg index =

The assessment standards are the following disease index proportion of area of injury%

о O ι + Пі + n ₂ + n ₃ + n ₄ 1 1-5 2 6-25 3 26-50 4 51 or more Number of leaves with a disease index of n ₀ 0 η. 1 η ₂ 2 Пз 3 ₄ 4 N = по

Test Example 2 Test for control of potato rape (curative effect)

A zoospore suspension was prepared from Phytophthora infestans cultivated on a potato disk for 7 days and inoculated by spraying on potatoes (variety "Danshaku", plant height about 25 cm) grown in pots in a greenhouse. The pots were left at 17-19 ° C. for 20 h and then the chemical at a predetermined concentration (obtained by preparing a wettable powder of each test compound according to the method of Formulation Example 8 and diluting it with water to the predetermined concentration) was applied to the potato plants in an amount of 50 ml / 3 pots using a Spray gun (1.0 kg / cm ² ) sprayed and then air dried The pots were left for 6 days at a temperature of 17-19 ° C and a humidity of more than 95%, and then the degree of formation of Damage Examines The standards for the assessment and the method to address the damage index were as in Test Example 1

Test Example 3 Test to control the downy mildew of the cucumber (preventive effect)

The chemical was prepared at a predetermined concentration (obtained by preparing a wettable powder of each test compound according to the method of Formulation Example 8 and diluting it with water to a predetermined concentration) on cucumbers (variety Sagami hanjiro) at the stage where two main leaves were developed ), which were grown in pots in a greenhouse, sprayed in an amount of 30 ml / 3 pots using a spray gun (1.0 kg / cm ² ) and air-dried. From the damage to the powdery mildew-infected cucumber leaves Pseudoperonospora cubenis and provided a spore suspension using deionized water ago and inoculated by spraying on the cucumber Immediately then, the inoculated pots were incubated at a temperature of 18 to 20 ^0C and a humidity of more than 95% during 24 h unddannmein greenhouse left (in 18bis27 ° C) convicted 7-day-father became the degree Damage Assessment The standards for evaluation and the method of indicating the damage index were as in Test Example 1

Test Example 4 Test to control the downy mildew in the cucumber (healing effect)

As in Test Example 3, a spore suspension of Pseudoperonospora cubenis was prepared and inoculated by spraying onto the same cucumber as used in Test Example 3. Immediately thereafter, the inoculated pots were kept at a temperature of 18 to 20 ° C and a humidity of more for 24 hours left as 95% The chemical was used in a predetermined concentration (obtained by preparing a wettable powder of each test compound according to the method of Formulation Example 8 and diluting it with water to the predetermined concentration) on the cucumber in an amount of 30 ml / 3 pans a spray gun (1.0 kg / cm ²⁾ was sprayed and dried in the air the pots were then in a greenhouse (at 18 to 27 ⁰ C) überfuhrt and 7 days later for the degree of formation of lesions examined the standards for the evaluation and The method of displaying the damage index was as in Test Example 1

Test Example 5 Tomato herb lax control test (bottom penetration)

The chemical was prepared at a predetermined concentration (obtained by preparing a wettable powder of each test compound according to the method of Formulation Example 8 and diluting it with water to a predetermined concentration) by dripping in the soil near the roots of tomato (variety Sekaichi, H 20cm) grown in pots (7.5cm diameter) in a greenhouse, added by pipette at a rate of 2ml / pot. The pots were then left in the greenhouse for 5 days. A zoospore suspension of Phytophthora infestans was prepared The suspension was then inoculated by spraying on the chemical treated tomato plants. The test plants were kept at a temperature of 17-19 ° C and a humidity of more than 95%, and the degree was examined the formation of damage The standards of assessment and method, d In the above test examples, the concentration of the active ingredients was adjusted to 100 ppm in the case of spraying and 15 g / Ar in the case of soil penetration. The results of the above test examples are shown in Table 3

Test Example 6 Test to control the downy mildew of the cucumber (healing effect and remaining effect)

Pseudoperonospora cubenis was harvested from damage to cucumber leafs (variety Sagami hanjiro, at the stage where 3 main leaves were developed) grown in pots in a greenhouse and prepared a spore suspension of fungus using deionized water. Spore suspension was inoculated by spraying on the cucumber plants The inoculated pots were left in the greenhouse for 24 hours, and the chemical was brought to a predetermined concentration (obtained by preparing a wettable powder of each test compound according to the test method of Formulation Example 18 or 19 and diluting it to the predetermined one Concentration) in an amount of 50 ml / 3 pots using a spray gun (1.0 kg / cm ² ) and dried in air. Thereafter, the pots were transferred to a greenhouse (18 to 27 ° C) and 10 and 18 days thereafter we investigated the degree of damage formation The results are given in Table 4. The standards of the evaluation and the method of indicating the damage index were as in Test Example 1

Test Example 7 Tomato herb rot control test (curative effect and residual effect)

A zoospore suspension of Phytophthora infestans cultured on a potato disk for 7 days was prepared and inoculated by spraying on tomatoes (variety: Sekaiichi; plant height 20 cm) grown in pots in a greenhouse. The inoculated pots were left in a 16 ° C humid chamber for 24 hours, and a chemical was sprayed at a predetermined concentration (obtained by preparing a wettable powder of each test compound according to Formulation Example 18 or 19 and diluting it with water to the predetermined concentration ) on the plants in an amount of 50ml / 3 pots using a spray gun (1.0kg / cm ² ) and dried in air. The pots were transferred to a greenhouse (10 to 20 ° C), and 10 days and 11 days later, the degree of damage was evaluated. The results are shown in Table 5

 The standards of evaluation and the method of indicating the damage index were as in Test Example 1.

Test Example 8 Test for control of cucumber downy mildew (action on acylalanine-resistant chemicals)

Tribe)

The chemical was prepared in a predetermined concentration (obtained by preparing a wettable powder of each test compound according to Formulation Example 11 or 12 and diluting it with water to the predetermined concentration) on the cucumbers (variety: Sagami hanjiro; the stage in which the three main leaves were developed were), grown in pots in a greenhouse, sprayed in an amount of 50 ml / 3 pots using a spray gun (1.0 kg / cm ² ) and air-dried. Both the acylalanine fungicide resistant and susceptible Pseudoperonospora cubenis strain were harvested from the cucumber leaf damage infected with downy mildew. They were mixed and a spore suspension was made from the mixture. The spore suspension was then inoculated on the treated cucumber leaves by spraying. The inoculated pots were left in a humid chamber for 24 h at 20 ⁰ C and then transferred to a greenhouse (18 to 27 ° C). 10 and 18 days later, the degree of damage was assessed. The damage index was determined as in Test Example 1. The results are shown in Table 6.

Test Example 9 Test for the control of early tomato rot

The chemical was prepared in a predetermined concentration (obtained by preparing a wettable powder of each test compound according to Formulation Example 18 and diluting it with water to the predetermined concentration) on the tomatoes (variety: Sekaiichi; plant height about 20 cm) grown in pots in a greenhouse, sprayed in an amount of 50 ml / 3 pots using a spray gun (1.0 kg / cm ² ) and dried in air. A spore suspension of Alternaria solani cultured in a PSA medium was prepared and inoculated on the tomato in the pots by spraying. The pots were placed in a greenhouse (25 to 33 "C) was transferred, and 10 days later they examined the degree of formation of lesions. The injury index was determined as in Test Example 1 and the results are shown in Table 7.

The results given in Table 3 demonstrate that the compounds described have excellent control over plant diseases caused by oomycetes, such as potato herb rot, tomato herb rot and cucumber downy mildew, when applied not only by spraying, but also by cucumber also by soil saturation whereas the comparative compounds M and N, which are considered relatively similar to the compounds, show little or no control effect on these plant diseases. Furthermore, the compounds produced have a preventative effect at much lower dosages than commercially available and widely used against these plant diseases zinc ethylene bis (dithiocarbamate) and tetrachloroisophthalonitrile and have a curative effect, these two have not commercially available chemicals. Accordingly, the compounds can show a good control effect even when applied after the infection of the crops with these diseases. Thus, this can greatly change the disease control system for crops in agriculture and horticulture and obviously contribute greatly to saving labor on the part of the breeder. Since the compounds have a good control effect when applied by soaking in the soil, they enable the part of a plant which is believed not to be reached by the chemical by spraying alone to be protected from disease.

The results given in Tables 4 and 5 show that the agricultural and horticultural fungicidal composition of the present invention has a superior control effect at lower dosages than is the case when applying dithiocarbamates, N-haloalkylthioimides, inorganic copper fungicides, TPN or thiazole and isothiazole derivatives prepared according to the invention as active ingredients. Obviously, a synergistic effect is found due to the mixing, and the remaining effect is greatly enhanced.

The results given in Table 7 show that the agricultural horticultural fungicidal composition of the present invention has an excellent control effect on a wide range of plant diseases caused by phytopathogenic fungi, such as Alternaria solani, Pseudoperonospora cubenis and Colletotrichum lagenarium, which are taxonomically removed from each other are. This means that in the cultivation of crops, application of the agricultural and horticultural fungicidal composition can control a variety of co-occurring plant diseases which are difficult to control simultaneously with the aid of conventional fungicidal compounds.

As shown in Table 6, the fungicidal composition of the invention for agriculture and horticulture has an excellent control effect against a wide range of plant diseases caused by Oomycetes, whose resistance to fungicidal chemicals is a serious problem. In particular, the fungicidal composition of the invention for agriculture and horticulture shows a much better control effect at lower dosages than in the case of the sole use of acylalanine fungicides (such as metalaxyl, furalaxyl, benalaxyl, oxadixyl, Ofurace and Cyprofuram), thiazole derivatives and isothiazole derivatives, the active ingredients this composition. Obviously, a synergistic effect appears as a result of mixing.

Table 3

Test for diseases of the potato, cucumber and tomato

Test compound no.

damage Index

Kartoffelkrautfäule

preventive

healing

Downy mildew at d. cucumber

preventive

healing

Tomato herb rot soil soak

2 0 0 0 0 0 3 0 - 0 0 0 4 0 0 0 0 0 5 0 0 0 0 0 6 0 - 0 0 0 7 0 0 0 0 0 8th 0.3 - 0.2 0 0.2 9 0 0 0 0 0 10 0 - 0 0 0 11 0 0 0 0 0 12 0 0 0 0 0 13 0 - 0 0 0 14 0 0 0 0 0 15 0 0 0 0 0 16 0 - 0 0 0 17 0 0 0 0 0 18 0 - 0 0 0 19 0 0 0 0 0 20 0 0 0 0 0 21 0 - 0 0 0 22 0 0 0 0 0 25 0 - 0 0 0 26 0 0 0 0 - 32 0 0 0 0 0 33 0 0 0 0 0 34 0 0 0 0 0 35 0 0 0 0 0 36 0 - 0 0 0 38 0 0 0 0 - 39 0 - 0 0 0 40 0 0 0 0 - 41 0 - 0 0 0 42 0.5 0.6 0.3 0.3 - 43 1.2 - 1.2 1.0 - 44 0 0 0 0 - 45 0 0 0 0 - 46 0 - 0 0 0 47 0 0 0 0 - 48 0 0 0 0 - 50 0 0 0 0 0 51 0 0 0 0 0 52 0 0 0 0 0 53 0 0 0 0 0 54 0 0 0 0 0

Table 3 (continued)

Test compound no.

damage Index

Kartoffelkrautfäule

Downy mildew at d. cucumber

Table 4

Test for bad mildew in cucumber. Tomato herb rot

Preventing Hello Preventing Hello Soil drenched 55 - - 0 0.5 - 56 - - 0.3 0.5 - 58 0 - 0 0 - 59 0 0 0 0 0 60 0 0 0 0 - 61 0 0 0 0 - 62 0 0.4 0 0 - 65 - - 0 0 - 71 - - 0 0.2 - 73 - - 0 0.2 - M 2.0 2.4 2.1 2.4 3.2 N 2.0 2.5 1.9 2.3 3.0 B 2.3 3.8 2.0 3.4 3.8 e 2.4 3.6 2.5 3.7 3.7 untreated 3.7 3.8 3.7 3.7 3.8

Test compound no. Concentration of the active substance (ppm) Damage index 10 days 18 days later later 0.7 1.0 2 100 50 0 0 1.0 1.3 3 100 50 0 0 0.7 1.0 4 100 50 0 0 1.0 1.0 5 100 50 0 0 1,0 1,5 6 100 50 0 0 0.8 0.8 17 100 50 0 0 0.6 0.7 18 100 50 0 0 2.9 A 500 2.9 3.0 C 500 3.0 3.7 D 500 3.5 3.1 e 500 3.0 2.8 F 500 2.7 0 0 2 + A 100 + 500 50 + 500 0 0 0 0 3 + A 100 + 500 50 + 500 0 0 0 0 4 + A 100 + 500 50 + 500 0 0

Table 4 (continued)

Test compound no. Concentration of the active substance (ppm) Damage index ЮТаде 18Таде later later 0 0 5 + A 100 + 500 50 + 500 0 0 0 0 2 + C 100 + 500 50 + 500 0 0 0 0 6 + C 100 + 500 50 + 500 0 0 0 0 17 + C 100 + 500 50 + 500 0 0 0 0 18 + C 100 + 500 50 + 500 0 0 0 0.5 3 + D 100 + 500 50 + 500 0 0 0 0.2 5 + D 100 + 500 50 + 500 0 0 0,1 0,5 18 + D 100 + 500 50 + 500 0 0 0 0 2 + E 100 + 500 50 + 500 0 0 0 0 6 + E 100 + 500 50 + 500 0 0 0 0 17 + E 100 + 500 50 + 500 0 0 0 0 18 + E 100 + 500 50 + 500 0 0 0 0 2 + F 100 + 500 50 + 500 0 0 0 0 4 + F 100 + 500 50 + 500 0 0 0 0 5 + F 100 + 500 50 + 500 0 0 3.7 untreated - 3.7

Table 5

Tomato herb test

Test compound no. Concentration of the active substance (ppm) Damage index ЮТаде 18 days later later 0.8 1.2 2 100 50 0 0 1.1 1.4 6 100 50 0 0 0.7 1-0 12 100 50 0 0 0.6 0.9 13 100 50 0 0 1.0 1.0 50 100 50 0 0 1.0 1.8 54 100 50 0 0 3.5 A 500 3.3 3.6 C 500 3.5 3.5 D 500 3.5

Table 5 (continued)

Test compound no. 2 + A Concentration of the active substance (ppm) Damage index 10 days 18 days later later 3.4 e 6 + A 500 3.0 3.0 F 13 + A 500 3.0 0 0 54+ A 100 + 500 50 + 500 0 0 0 0 2 + C 100 + 500 50 + 500 0 0 0 0 6 + C 100 + 500 50 + 500 0 0 0 0.4 50+ C 100 + 500 50 + 500 0 0 0 0 12 + D 100 + 500 50 + 500 0 0 0 0 13 + D 100 + 500 50 + 500 0 0 0 0 54+ D 100 + 500 50 + 500 0 0 0.1 0.3 2 + E 100 + 500 50 + 500 0 0 0 0 6 + E 100 + 500 50 + 500 0 0 0.4 0.7 50+ E 100 + 500 50 + 500 0 0.1 0 0.4 6 + F 100 + 500 50 + 500 0 0 0 0 50+ F 100 + 500 50 + 500 0 0 0 0 54+ F 100 + 500 50 + 500 0 0 0 0 untreated 100 + 500 50 + 500 0 0 0 0 100 + 500 50 + 500 0 0 0 0 100 + 500 50 + 500 0 0 3.8 - 3.6

Table 6

Test for the wrong mildew in cucumber

Test compound no. Concentration of the active substance (ppm) Damage index 10days 18 days later 0.6 1.1 2 200 100 0 0 1,0 1,5 4 200 100 0 0 0.9 1.5 5 200 100 0 0 2.0 2.0 6 200 100 0 0.5 3.0 3.5 G 200 100 CN CN CN 2.8 3.5 H 200 100 2,2 2,5 2,0 2,2 I 200 100 1.7 1.6 3,1 3,3 J 200 100 2,0 2,5 1.8 2.5 К 200 100 1.5 1.9 2.0 2.8 L 200 100 1.3 1.3 0 0 2 + G 50 + 50 50 + 100 0 0 0 0 4 + G 50 + 50 50 + 100 0 0 0 0 5 + G 50 + 50 50 + 100 0 0 0 0 6 + G 50 + 50 50 + 100 0 0 0 0 2 + H 50 + 50 50 + 100 0 0 0 0 4 + H 50 + 50 50 + 100 0 0 0 0 5 + H 50 + 50 50 + 100 0 0 0.2 0.2 6 + H 50 + 50 50 + 100 0 0 0 0 2 + 1 50 + 50 50 + 100 0 0 0 0 4 + 1 50 + 50 50 + 100 0 0 0 0 5 + 1 50 + 50 50 + 100 0 0 0.3 0.1 6 + 1 50 + 50 50 + 100 0 0 0 0 2 + y 50 + 50 50 + 100 0 0 0 0 4 + y 50 + 50 50 + 100 0 0 0 0 5 + y 50 + 50 50 + 100 0 0 0.3 0.1 6 + y 50 + 50 50 + 100 0 0

Table 6 (continued)

Test compound no. Concentration of the active substance (ppm) - Damage index 10 days 18 days later later 0 0 2 + K 50 + 50 50 + 100 0 0 0 0 4 + K 50 + 50 50 + 100 0 0 0 0 5 + K 50 + 50 50 + 100 0 0 0.3 0.2 6 + K 50 + 50 50 + 100 0 0 0 0 2 + L 50 + 50 50 + 100 0 0 0 0 4 + L 50 + 50 50 + 100 0 0 0 0 5 + L 50 + 50 50 + 100 0 0 0 0 6 + L 50 + 50 50 + 100 0 0 3.5 untreated 3.4

Table 7

Test for early rot in tomato

Test compound no. 2 + A Concentration of the active substance (ppm) Damage index 2 3 + A 100 2.6 3 12 + A 100 3.0 4 4 + E 100 3.1 6 6 + E 100 3.0 12 18 + E 100 2.7 18 2 + F 100 2.9 A 3 + F 500 0.8 e 12 + F 500 0.7 F untreated 500 1.0 100 + 500 0 100 + 500 0 100 + 500 0 100 + 500 0 100 + 500 0 100 + 500 0 100 + 500 0 100 + 500 0 100 + 500 0 - ?

Claims (9)

1. A fungicidal composition for agriculture and horticulture, characterized in that it comprises a diluent or a carrier and / or an adjuvant and as the first active ingredient at least one amide derivative of the following general formula (I) wherein one of X and Y represents a sulfur atom and the other represents a carbon atom, Z represents a nitrile or thioamide group, each of R ¹ and R ^{2 represents} a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, a halomethyl group or a phenyl group; and R ^{3 is} an alkenyl group having 2 to 4 carbon atoms, a haloalkenyl group having 2 to 4 carbon atoms, a furyl group, a thienyl group, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, an alkynyloxy group having 3 to 5 Carbonyl, an alkynylthio group having from 3 to 5 carbon atoms, a pyrazolyl group or an unsubstituted or halogeno-substituted phenyl group, and as the second active ingredient at least one component selected from acylalanine fungicides having control activity with respect to plant diseases caused by oomycetes, dithiocarbamate fungicides, N- Haloalkylt Hioimid fungicides, inorganic copper fungicides, TetracMorisophthalonitrile, Dichlofluanid and fluazinam. 2. Composition according to claim 1, characterized in that the second active ingredient is at least one acylalanine fungicide with control efficacy against plant diseases caused by Oomycetes. 3. The composition according to claim 1, characterized in that the second active ingredient is at least one component selected from dithiocarbamate fungicides, N-haloalkylthioimide fungicides, inorganic copper fungicides, Tetrachlorisophthalonitril, Dichlofluanid and fluazinam. 4. The composition according to claim 1, characterized in that the second active ingredient is a dithiocarbamate fungicide. 5. The composition according to claim 1, characterized in that the second active ingredient is an N-haloalkylthioimide fungicide. 6. The composition according to claim 1, characterized in that the second active ingredient is an inorganic copper fungicide. 7. The composition according to claim 1, characterized in that the second active ingredient is tetrachloroisophthalonitrile. 8. The composition according to claim 1, characterized in that the second active ingredient is dichlofluanid. 9. The composition according to claim 1, characterized in that the second active ingredient is fluazinam.