MXPA97001459A - Microbic composition - Google Patents

Abstract

The present invention relates to a microbicidal composition comprising as active ingredients: (I) a dithiocarbonimide compound represented by the general formula (I): wherein Z represents a CH group or a nitrogen atom, R1 and R2 are the same or different and represent a hydrogen atom, an alkyl group of 1 to 6 carbon atoms, a halogen atom, an alkoxy group of 1 to 6 carbon atoms, a haloalkyl group of 1 to 6 carbon atoms or a haloalkoxy group of 1 to 6 carbon atoms, or R1 and R2, taken together, form a methylenedioxy group optionally substituted with a fluorine atom, and (II) at least one compound selected from the group consisting of ethylenebis (dithiocarbamate), copper compound, phthalimide microbicide compound, Chlorothalonil, microbicidal compound of anilide, cymoxanil, dimetomorph and foset

Description

MICROBICIDE COMPOSITION FIELD OF THE INVENTION The present invention relates to a microbicidal composition. More particularly The present invention relates to a microbicidal composition that shows the superior effects of controlling diseases caused by Oomycetes. BACKGROUND OF THE INVENTION To date, numerous microbicidal compositions have been known. However, many of the diseases caused by Oomycetes present the rapid development of the symptoms of the disease once the plant is attacked by Oomycetes and this pathogenic microorganism rapidly spreads by secondary infection. Therefore, diseases caused by Oomycetes are difficult to control effectively. Thus, there is a great demand for a microbicidal composition that shows the superior effects of controlling the diseases caused by Oomycetes. OBJECTIVES OF THE INVENTION A main objective of the present invention is to provide a microbicidal composition having the superior effects of controlling diseases caused by Oomycetes.

REF: 24150 This objective, as well as other objectives and advantages of the present invention, will be apparent to those skilled in the art after reading the following description. BRIEF DESCRIPTION OF THE INVENTION The present invention solves the above problems and provides a microbicidal composition comprising as active ingredients: (I) a dithiocarbonimide compound (hereinafter referred to as "compound (I)"), represented by the general formula : or wherein Z represents a CH group or a nitrogen atom, R 1 and R 2 are the same or different and represent a hydrogen atom, an alkyl group of 1 to 6 carbon atoms, a halogen atom, an alkoxy group of 1 to 6 carbon atoms, a haloalkyl group of 1 to 6 carbon atoms or a haloalkoxy group of 1 to 6 carbon atoms, or R and R, all comatose, form an optionally substituted methylene dioxide group with a fluorine atom and (II) at least one compound (hereinafter referred to as "compound (II)" J which is selected from the group consisting of eti lenbis (dithiocarbamate), copper compound, phthalimide microbicide compound, chlorotaioni i, microbicidal compound of anuide, cymoxanil, dimethomorph and fosetii.- DETAILED DESCRIPTION OF THE INVENTION First, compound (I) will be explained In the above general formula, examples of alkyl groups of 1 to 6 carbon atoms represented by R "i and R2, they are methyl and ethyl groups. The atoms of the halogen atom are fluorine and chlorine atoms. Examples of the alkoxy group of 1 to 6 carbon atoms are methoxy and ethoxy groups. An example of a haloalkyl group of 1 to 6 carbon atoms is the trifluoromethyl group 1.

An example of a haloalkoxy group of 1 to 6 carbon atoms is a trifluoromethoxy group. The compound (I) can be prepared by a method described in European Patent EP-A-0656351. The modalities of the compound (I) are shown together with the numbers of the compound in Table 1 (the modalities are shown by the definition of the respective substituents in the compound represented by the general formula).

Compound No. X R1 R2 (la) CH CH3 H (Ib) CH C2H5 H lie) CH OC2H5 H (Id) CH CF3 H (le) CH OC2H5 F (If) CH OCF20 dg) N OC2H5 H (Ih) CH CF30 H Next, compound (II) will be explained. Each page that is mentioned after the name of each compound represents the page number in which the compounds are described in The Pesticide Manual, Tenth Edition (edited by Clive To lin, published by The British Crop Protection Council and The Royal Society of Chemistry, 1994): In the present invention, the ethylenebis (dithiocarbamate) compound means a salt of ethylenebis- (dithiocarbamate) such as the zinc salt [general name; zineb, chemical name; zinc eti (zinc dithiocarbamate) (polymeric), page 1048], manganese salt [general name]; maneb. chemical name; ethylenebis - '? it locarbamate) of manganese (polymeric), page 637] and zinc and manganese salt [general name; manzeb, another name; mancozeb, chemical name; ethylenebis- (dithiocarbonate) manganese (polymeric) complexed with zinc salt, page 635]. The copper compound means an inorganic copper salt. which is used as a microbicidal agent "such as chloride, oxychloride [general name: basic copper chloride (copper oxychloride), chemical name trihydroxychloride dicobre (approximate composition), page 230], carbonate, oxide, hydroxide, sulfate ( page 231), phosphate, silicate, zinc chromate and hydrazinium sulfate) and an organic copper salt, which is used as a microbicidal agent "such as acetate, 8-hydroxyquinol inolate [general name; oxina-copper, chemical name; 8-quinol cupric inoxide. page 758], oxalate. bis (3-feni lsal icilato). Naphthalene (page 716). Linolenate and oleate} . The phthalimide microbicide compound means N- (trichloromethyl Itio) phthalimide "general name, flopet, page 518. which is a compound having an N-substituted phthalimide structure, and N- (trichloro ethylthio) -c? Clohex- 4-en-l, 2-dicarboximide (general name, captan. page 145) and N- (1, 1, 2, 2-tetrachloroeti lthio) cyclohex-4-en-1,2-dicarboxamide (general name, captafol, page 143), which are compounds having a tetrahydrophthalide structure N -replaced. The term chlorothalonil (general name) means tetrachloroisophthalonitrile (page 193). The compound microbicide of anuide means a compound having the structure 2,6-dimethylanilide. such as metal xyl (general name) "chemical name; N- (2,6-dimethylphenyl) -N- (methoxyacetyl) laninate methyl, page 660.}., benalaxyl (general name)" chemical name; N- (2,6-dimethylphenyl) -N- (phenylacetyl) alaninate methyl, page 71), furalaxyl (general name) "chemical name: N- (2,6-dimethylphenyl) -N- (2-ur nylcarbonyl) methyl alaninate, page 534.}., ofurace (general name) "chemical name; 2-Chloro-N- (2,6-dimethyl-1-phenyl) -N- (tetrahydro-2-oxo-3-furanyl) -ettamide, page 745.). and oxadixyl (general name) "chemical name: 2-methoxy-N- (2-oxo-1,3-oxazolidin-3-yl) aceto-2 '.6'-xylidide, page 755.}. having the structure 3-chloroanilide, such as ciprofuram (general name) chemical name, N- (3-chloropheni1) -N- (tetrahydro-2-oxo-3-furani1) -cyclopropanecarboxamide, page 1076) Cimoxanil ( general name) means 2-cyano-NJ (etilamino) carbonyl -2- (methoximino) acetamide (page 257). ? i dimetomorfo (general name) means 4- [3-! - i rofeni 1) -3- (3.4-? imeto i feni 1) acri loi l] morfol ina i page 351). The fosetyl (general name) means hydrogen ethyl phosphate (page 530). The fosetyl can be used in salt form, such as an aluminum salt and the like. The microbicidal composition of the present invention can be used to control diseases caused by Piricularia oryzae, Cochl iobolus miyabeanus and Rhizoctonia solani of rice, Erysiphe graminis, f. sp. hordei, f. sp. tritici. Gibberella zeae. Puccinia striiformis, P. graminis, P. recondite, P. hordei. Typh la sp. Miconectriel the nivalis. Ustilago tritici, U. nuda, Tillßtia caries, Pseudocercosporel herpotrichoides, Rhizoctonia cereal is. Rhynchosporium secalis, Septoria tritici and Leptospheria nodorum of cereals, Diaporthe citri, Elsinoe fawcetti, Penicil lium digitatum, and P. italicum of orange. Sclerotinia mal i. Bad Valsa i. Podosphaera leucotricha. I would alternate badly and Venturia inaequalis of the apple, Venturia nashicola. It would alternate Kikuchiana and Gymnosporangium haraeanum of the pear, Sclerotinia cinerea, Cladosporium carpophi lum and Phomopsis sp. of the peach, Plasmopara viticola, Elsinoe ampelina, Flomerel the cingulata, Uncinula necator and Phakopsora ampelopsidzs of the vine, ßloeosporiu kaki. Cercospora kaki and Mycospharel the nawaß of the persimmon. Pseudoperonospora cubensis of cucumber. Col letotrichum lagenarium, Sphaerotheca ful iginea, Mycospaerel the melonis of the plants Cucurbitaceae, Alternaria solani. Cladosporium fulvum and Phytophthora infestans from tomato, Phomopsis vexans and Erysphe cichoracearum from eggplant. Alternate japonica and Csrcosporel the brassiecae of the Cruciferae plants, Puccinia there of the elsh onion, Cercospora kikuchii. Elsinoe glycines and Diaporthe phasßolorum var. sa ae of soy. Col letotrichum lindemthianum from beans, Mycosphaerella person tum and Cercospora arachidicola from peanuts, Erysiphe pisi and Peronospora pisi from pea. Peronospora viciae and Phytopfthora nicotianae of the kidney bean. I would alternate solani and Phytophthora infestans from the potato, Sphaetotheca humuli and Phitophthora nicotianae of strawberry.

Exobasidiu reticulatum and Elsinoe tea leucospila.

I would alternate longipes. Erysiphe cichoracearum.

Col letotrichum tabacum and Phytopfthora parasitic of tobacco. Cercospora baticola, Diplocarpon roses.

Sphaerotheca pannosa and Phytophtora megasperma of the rose.

Septoria chrysanthemi indici and Puccinia horiana of chrysanthemum. Botrytis cinerea and Sclerotinia sclerotiorum of various crops and various diseases caused by Pythium sp. In particular, the microbicidal composition of the present invention shows superior effects by its synergistic microbial effects to control diseases caused by Oomycetes. such as Peronospora. Phytophthora and diseases caused by Pythi u sp. In the microbicidal composition of the present invention, a mixing ratio of Compound (I) and Compound (II) is not limited to those specified. An amount of at least one compound that is selected from the group consisting of eti-lenbis compound (dithiocarbamate), copper compound, phthalimide microbicide compound, chlorothalonil and fosetyl. it is usually in the range of 0.1 to 100 parts by weight, preferably 0.5 to 50 parts by weight, based on one part by weight of Compound (I). An amount of the microbicide compound of anuide is usually in the range of 0.1 to 20 parts by weight, preferably 0.1 to 10 parts by weight, based on one part by weight of Compound (I). An amount of cymoxanil is usually in the range of 0.1 to 100 parts by weight, preferably 0.5 to 50 parts by weight, based on one part by weight of Compound (I). An amount of dimethomorph is usually in the range of 0.1 to 50 parts by weight, preferably 0.2 to 10 parts by weight, based on one part by weight of Compound (I).

The microbicidal composition of the present invention can be used merely by mixing the compound (I) and the Compound (II). However, the microbicidal composition of the present invention is normally used by formulating it into preparations such as in the form of water dispersible powder, suspension, granules, dry flow agent, emulsifiable concentrate, liquid formulation, • oil solution, smoking agent , aerosol agent and microcapsules. mixing Compound (I) and Compound (II). mixing said mixture with a solid vehicle, liquid vehicle and / or gaseous vehicle, and if necessary, adding thereto an adjuvant for preparations, such as a surfactant, an adhesive agent, a dispersing agent and a stabilizing agent. Alternatively, the microbicidal composition of the present invention can be used by formulating Compound (I) and Compound (II) in separate preparations, diluting each preparation with water and mixing both preparations. A total amount of the active compounds contained in these preparations is usually from 0.1 to 99% by weight, preferably from 0.2 to 90% by weight. Examples of solid carriers are pulverized or particulate clay particles (such as kaolin clay, diatomaceous earth, hydrated synthetic silicon oxide, attapulgite clay, bentonite and acid clay), talcs, other inorganic minerals (such as sericite, quartz powder). , sulfur powder, activated carbon, calcium carbonate and hydrated silica) and sal. for chemical fertilizers (such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea and ammonium chloride). Examples of liquid carriers are water, alcohols (such as methanol and ethanol), ketones, such as acetone, methyl ethyl ketone and cyclohexanone) aromatic hydrocarbons (such as benzene, toluene, xylene, ethylbenzene and methyl Inaftalene). aliphatic hydrocarbons (such as hexane and kerosene), esters (such as ethyl acetate and butyl acetate, nitriles (such as acetonitrile and isobutyronitrile), ethers (such as dioxane and diisopropyl ether), amides (such as dimethylformamide and dimeti lacetamide). Halogenated hydrocarbons (such as dichloroethane, trichlorethylene and carbon tetrachloride) Examples of gaseous vehicles are butane gas, gaseous carbonic acid and ganocarbon solvents Examples of the surfactant are alkylsulfuric esters, alkylsulfonates, alkylarylsulfonates, alkylaryl ethers and their polyoxyethylene compounds. , polyethylene glycol ether, multivalent alcohol ester and sugar alcohol derivatives.

Examples of the adhesive agent and the dispersing agent are casein, gelatin, polysaccharides (such as starch, acacia gum, cellulose derivatives and alginic acid). derivatives of lignin, bentonite, sugars and water soluble synthetic polymers (polyvinyl alcohol, polyvinylpyrrolidone and polyacrylic acid). Examples of the stabilizing agents are the PAP (isopropi Ifosfato acid), BHT (2,6- i-tert-butyl-4-methylphenol). BHA (mixture of 2-tert-butyl 1-4-methoxyphenol and 3-tert-butyl 1-4-methoxyphenol). vegetable oil, mineral oil and fatty acids or esters thereof. The preparations described above are applied to plants or soil as they are or diluted with water or the like. When the preparations are applied to the ground, these can be sprayed to the soil surface or can be used by applying them in a mixture with the soil. Alternatively, the preparations can be applied by various methods such as the seed treatment method and the ULV methods. When the preparations are used as a seed treatment agent, they are employed by a seed coating treatment, seed immersion treatment, seed spray treatment or the like. The microbicidal composition of the present invention can be used in conjunction with other microbicidal agents, insecticides, acaricides, nematicides, herbicides, seed disinfectants, fertilizers, soil conditioners and the like. An application amount of the microbicidal composition of the present invention depends on the type of active ingredient compound, the mixing ratio of Compound (I) and Compound (II), weather conditions, the manner of preparation , the time of application, the method of application, the place of application, the disease in question, the crop in question and the like, and a total amount of the active ingredient compound is usually 0.001 to-1000 g / area . preferably from 0.1 to 100 g / area. When the preparation is applied in the form of emulsifiable concentrate, water dispersible powder, suspension, liquid formulation or the like, the application concentration is usually from 0.0001 to 1% by weight, preferably from 0.001 to 0.5% by weight. The granules or powders or the like, are applied as they are. undiluted When it comes to treatments on the seeds, the total amount of active ingredient compounds to be applied is normally 0.001 to 50 g / kg of seeds, preferably 0.01 to 10 g / kg of seeds. The following Preparation Examples and Test Examples illustrate the present invention in greater detail, but should not be considered as limiting the scope thereof. The term "parts" means "parts by weight" unless otherwise indicated. EXAMPLE OF PREPARATION 1 A part of Compound (la), (Ib), (le), (Id) are thoroughly ground and mixed. (you). (If). (Ig) or (Ih) -5 parts of zineb, maneb, manzeb. comes out inorganic copper, comes out organic copper, folpet. captan, captafol, chlorothalonil, metalaxil, benalaxil, furalaxil, ofurace, oxadixil, ciprofuram, cimoxanil, dimetomorfo or fosetil; a part of hydrated synthetic silicon oxide; 2 parts of lignin calcium sulfonate; 30 parts of bentonite and 61 parts clay of kaolin, water is added to the mixture to knead well, followed by a granulation and dried, to obtain granules. PREPARATION EXAMPLE 2 5 parts of Compound (la) are thoroughly ground and mixed. (Ib) (Ic) (Id) (le), (If). (Ig) or (Ib); 5 parts of zineb. maneb. manzeb, inorganic copper salt, organic copper salt, folpet. captan, captafol, chlorothalonil, metalaxyl. benalaxyl furalaxil. ofurace oxadixil. ciprofuram, cymoxanil. dimethomorph or fosetyl; a part of hydrated synthetic silicon oxide; 2 parts of lignin calcium sulfonate; 30 parts of bentonite and 57 parts of kaolin clay, water is added to the mixture to knead well, followed by granulation and dried to obtain granules.

EXAMPLE OF PREPARATION 3 Perfectly grind and mix 0.5 parts of the Compound (the) (Ib), (him). (Id), (le), (If), (Ig) or (Ih); 2.5 parts of zineb. maneb, manzeb, inorganic copper salt, organic copper salt, folpet, captan. captafol, chlorothalonil, metalaxyl. benalaxyl furalaxil. ofurace oxadixil. ciprofuram cymoxanil, dimethomorph or fosetyl; 86 parts of kaolin clay and 11 parts of talc, to obtain a powder.

PREPARATION EXAMPLE 4 5 parts of Compound (a), (Ib), (le), (Id), (le), (If) are mixed and wet-milled. (Ig) or (Ih); 25 parts of zineb. maneb, manzeb, inorganic copper salt, organic copper salt, folpet, captan, captafol, chlorothalonil, metalaxil, benalaxil, furalaxil, ofurace, oxadixil, ciprofuram, cimoxanil. dimethomorph or fosetyl; 3 parts of polyoxyethylene monooleate lensorbitan; 3 parts of carboxymethylcellulose and 64 parts of water, until obtaining particles of a size less than 5 microns, to obtain a suspension.

EXAMPLE OF PREPARATION 5 Perfectly grind and mix 10 parts of the Compound (the) (Ib), (le), (Id), (le), (If), (Ig), or (Ih); 50 parts of zineb, maneb, manzeb. Inorganic salt of copper, organic salt of copper. folpet, captan, captafol, chlorothalonil, metalaxyl, benalaxyl. furalaxil, ofurace. oxadixyl, metalaxyl, benalaxyl, furalaxyl, ofurace, oxadixyl, ciprofuram, cymoxanil, dimethomorph or fosetyl; 3 parts of lignin calcium sulfonate; 2 parts of sodium lauryl sulfate and 35 parts of hydrated synthetic silicon oxide, to obtain a water-dispersible powder. The following Test Examples indicate that the microbicidal composition of the present invention has excellent activity for controlling diseases. The control effect, which is expected when the treatment is carried out by mixing the two given types of active ingredient compounds, is usually calculated with the following Colby equation. E = X + Y - X_ Y 100 X: Control value (%) when the treatment is carried out using a compound A of active ingredient at the concentration of m ppm.

Y: Control value. { %) when the treatment is carried out using a compound B of active ingredient at the concentration of m ppm. E: Control value. { %) when the treatment is carried out using compound A of active ingredient at the concentration of m ppm and compound B of active ingredient at the concentration of n ppm (hereinafter referred to as "expected control value"). If the control value (%) when the treatment is carried out by mixing two types of active ingredient compounds is greater than the expected control value (%), it can be said that the 3-energetic effect exists in a combination of these compounds. EXAMPLE OF TEST 1 A plastic container was filled with sandy loam, a vine was planted (fruit A) in the same »the vine was grown for 40 days in a greenhouse. A test preparation which was formulated as a water dispersible powder according to Preparation Example 5 was diluted with water to a predetermined concentration. The diluted test preparation was sprayed on the foliage of the seeded vine, which had developed 3 true leaves, in such a way that the dew effectively joined the surface of the leaves. Afterwards, the outbreak was inoculated by spraying with a suspension of zoosporangia from Plasmopara viticola. After the inoculation, the shoot was placed at high humidity at 23"C overnight, was grown for 7 days in a greenhouse, the severity was investigated (%) and the actual control value (%) was obtained according to with the following equation: Control value (%) ** "[Severity of the untreated pest (%) - severity of the treated plant (%)] / [severity of the untreated plant (%)]} X 100 The results are shown in Table 2.

Table 2 Concentration Control value Control value of the expected real ingredient Test set active (* l (*) (pp- *) (la) + manzeb 0.8 + 0.11 90 63 (Ib) + manzeb 0.8 + 0.11 94 74 (Is) + manzeb 0.8 + 0.11 90 66 Concentration Control value Control value of the expected real ingredient Active test time 1 * 1 1 * 1 IPPB) (the) + oxychloride of 0. 8 + 11 83 60 CODG * (le) + oxychloride of 0.8 + 11 80 64 copper (Ig) + oxychloride of 0.8 + 11 90 72 copper (la) + folpet 0.8 + 8 90 55 (Ib) + folpet 0.8 + 8 92 67 (Id) + folpet 0.8 + 8 88 60 Ka) + chlorotalone .1 0.8 + 10 70 53 I (c) + chlorotaloni .1 0.8 + 10 70 57 Kg) + chlorotaloni .1 0.8 + 10 80 67 Ka) r metalaxyl 0.8 + 0.5 90 68 Kb) + metal il 0.8 + 0.5 95 76 Kg) + metalaxyl 0.8 + 0.5 95 77 (Ib) + cymoxanil 0.8 + 30 82 67 (le) + cimoxanil 0.8 + 30 76 60 (Id) + cimoxani 1 0.8 + 30 70 51 Concentration Control value Control value of the expected real ingredient Active test set (*) (ti (ppi) (the) + dimetomorph 0.8 + 1 85 60 (le) + dimetomorph 0.8 + 1 85 64 (Ig) + dimetomorph 0.8 + 1 90 72 Ka) + fosetil 0.8 + 8 90 50 (Ib) + fosetil 0.8 + 8 95 63 (Id) + fosetil 0.8 + 8 90 45 (la) 0.8 50 - (Ib) 0.8 63 - (le) 0.8 55 - (Id) 0.8 45 - (Ig) 0.8 65 - Manzeb 11 25 - Oxi chloride of copper 11 20 - Folpet 8 10 - Chlorothalonil 10 5 - Metalaxyl 0.5 35 - Cimoxanil '30 10 - Dimetomorph 1 20 - Fosethyl 8 0 - EXAMPLE OF TEST 2 A plastic container was filled with sandy loam, a tomato plant (Ponterosa) was seeded therein, the tomato was grown during 20 days in a greenhouse. A test preparation, which was formulated in suspension according to Preparation Example 4, was diluted with water to a predetermined concentration. The diluted test preparation was sprayed on the foliage of the tomato plant, which had developed two true leaves, so that the spray effectively bound to the surface of the leaves. Afterwards, the shoot was inoculated by spraying with "a suspension of zoosporangia of Phytophthora infestans." After inoculation the shoot was placed at high humidity at 23 ° C overnight, grown for 4 days in a greenhouse, the severity (%) and the actual control value (%) was obtained in accordance with the previous equation.The results are shown in Table 3. - -, - > - Table 3 Concentration Control value Control value of the expected real ingredient Active test set (* l (*) (ppa) (the + manzeb 12.5 + 12.5 100 90 (Ib + manzeb 12.5 + 12.5 100 95 (Id + manzeb 12.5 + 12.5 100 85 Kb + chlorothalonil 12.5 + 12.5 100 95 I (c + chlorothalonil 12.5 + 12.5 100 96 Kd + chlorothalonil 12.5+ 12.5 100 85 Ka + metalaxyl 12.5 + 12 * .5 100 85 Kb + metalaxyl 12.5 + 12.5 100 93 Kc + metalaxyl 12.5 + 12.5 100 94 Kd + metalaxyl 12.5 + 12.5 100 78 He + metalaxyl 12.5 + 12.5 100 94 I (f + metalaxyl 12.5 + 12.5 100 90 Kg + metalaxyl 12.5 + 12.5 100 94 I (h + mßtalaxyl 12.5 + 12.5 100 93 (Ib + cyanoxanil 12.5 + 50 100 93 (le + cymoxanil 12.5 + 50 100 95 (ig + cymoxanil 12.5 + 50 100 95 Concentration 1 Control value Control value of the expected real ingredient Coapuesto ae active test (II («1 (ppi) (the) + dimetomor fo 12.5 + 12. 5 100 92 (le) + dimetomor fo 12.5 + 12. 5 100 95 (Ig) + dimetomor fo 12.5 + 12. 5 100 95 (la) 12.5 80 - (Ib) 12.5 90 - (le) 12.5 92 - (Id) 12.5 70 - (le) 12.5 92 - (If) 12.5 86 - (Ig) 12.5 92 - (Ih) 12.5 90 - Manzeb 12.5 50 - Chlorothalonil 12.5 50 - Metalaxyl 5 25 - Cimoxanil 50 33 - Dimetomorph 12.5 60 - The following Preparation Example illustrates the preparation of Compound (I) used in the present invention.

Example of Preparation of References [Preparation of Compound (le)] Carbon disulphide (2.0 g, 26 mmol) was added to a mixture of 4-ethoxy-3-f luoroani 1 ina (2.7 g, 17 mmol) and tritylamine ( 4.0 g, 40 mmol) under stirring. The mixture was stirred at room temperature for 10 hours, N.N-dimethyl formamide (30 ml) was added and methyl iodide (2.2 g, 16 mmol) was added dropwise. The mixture was stirred at room temperature for 30 minutes and dilute hydrochloric acid was added, followed by extraction with diethyl ether. The organic phase was washed with a saturated solution of sodium chloride, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (elution solvent: hexa? O / ethyl acetate, 4: 1). to obtain methyl 4-ethoxy-3-fluorofeni-l-dithiocarbamate (2.5 g, 10 mmol) in the form of crystals; p.f. - 108. O'C. To a solution of 4-ethoxy-3-fluorophenyldithiocarbamate (0.40 g, 1.6 mmol) in tetrahydrofuran (20 ml) was added sodium hydride (60% oil dispersion, 60 mg, 1.5 mmol) at room temperature. The mixture was stirred at room temperature for 30 minutes and (E) -methoximino-2- (2-bromoeti lfeni 1) -N-methylacetamide (0.42 g, 1.5 mmol) was added. The mixture was stirred at room temperature for 30 minutes and water was added, followed by extraction with ethyl acetate. The organic phase was dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (elution solvent: hexane / ethyl acetate, 1: 1). to obtain (E) -2-methoximino-2- [2- (4-ethoxy-3-f-lorof nor 1-imino) - (methylthio) met i 1-tofeni 1] -N-methylacetamide (0.60- g 1.3 mmol) ) in the form of an oil. - H-NMR (CDC13 / TMS, 6 (ppm)) 1.26 (3H.t. J = 7.1 Hz). 2.45 (3H. S). 2.88 (3H.D. J = 4.6 Hz). 2.95 (3H. S). 4.12 (2H, q, J = 7.1 Hz), 4.22 (2H, br s), 6.55-7.50 (8H.). Some NMR data of other compounds used in the present invention are shown below. Compound (la): 1 H-NMR (CDC13 / TMS.6 (ppm)) 2.46 (3H, s). 2.89 (3H. d, J = - 5.0 Hz). 3.95 (3H, s), 4.21 (2H, br s), 6.51-7.46 (8H, m). Compound (If): H-NMR (CDC13 / TMS, d (ppm)) 2.31 (3H.s), 2.44 (3H.s), 2.86 (3H.sup.-J-5.0 Hz). 3.95 (3H. S). 4.22 (2H. Br s). 6.72-7.49 (9H.m). It is noted that in relation to this date, the best method known to the applicant to carry out the aforementioned invention, is that which is clear from the present description of the invention. Having described the invention as an antecedent, what is contained in the following is claimed as property.

Claims (4)

1. CLAIMS 1. A microbicidal composition characterized in that it comprises as active ingredients: (I) a dithiocarbonimide compound represented by the general formula:
2. OR wherein Z represents a CH group or a nitrogen atom, R 1 and R 2 are the same or different and represent a hydrogen atom, an alkyl group of 1 to 6 carbon atoms, a halogen atom, an alkoxy group of 1 to 6 carbon atoms, a haloalkyl group of 1 to 6 carbon atoms or a haloalkoxy group of 1 to 6 carbon atoms. or R 1 and R 2, taken together, form a methylenedioxy group optionally substituted with a fluorine atom, and (II) at least one compound selected from the group consisting of ethylenebis (dithiocarbamate). copper compound, phthalimide microbicide compound. chlorotaioni 1. microbicidal compound of anuide, cymoxanil, dimetomorph and fosetil. 2. A microbicidal composition according to claim 1, characterized in that the eti-lenis (dithiocarbamate) compound is at least one member that is selected from the group consisting of zineb, maneb and manzeb, the copper compound is at least one member which is selected. from the group consisting of inorganic copper salts and organic copper salts, - the phthalimide microbicide compound is at least one member that is selected from the group consisting of folpet. capture and captafol. and the "microbial compound" is at least one member selected from the group consisting of metalaxyl, benalaxyl, furalaxyl, ofurace, oxadixyl and ciprofuram.
3. 3. A method to control diseases caused by fungi Oomycetes. characterized in that it comprises applying the composition according to any of claims 1 or 2. to a place where the fungi Oomycetes are propagated.
4. 4. The use of the composition according to any of claims 1 or 2, to control diseases caused by Oomycete fungi.