RU2203546C2 - Composition for preventing fungous diseases in cultivated plants and method for preventing them - Google Patents

Abstract

FIELD: agriculture. SUBSTANCE: the described composition contains a) imidazole compound of formula (1)

Description

FIELD OF THE INVENTION
The invention relates to compositions with a markedly enhanced effect on harmful bioorganisms, in particular with a therapeutic and / or prophylactic effect against plant diseases, which is useful in agriculture and horticulture; to a method of suppressing harmful bio-organisms using this composition and to a method of enhancing the suppressing effect of harmful bio-organisms, means for controlling harmful bio-organisms.

State of the art
With regard to the combination of active ingredients (a) and (b) used in the present invention (described later), European patent EP 298196 teaches that the imidazole compound used in the present invention as active ingredient (a) is useful as an agent to combat harmful bio-organisms, and the possibility of using the compound if necessary in combination with other fungicides is mentioned. EP 298196 also reports that the combined use of an imidazole compound, similar in structure to the imidazole compound used in the present invention, as active ingredient (a), with other fungicides such as cyanoacetamides (e.g. 1- (2-cyano-2 -methoxyiminoacetyl) -3-ethylurea) and chlorine-containing organic compounds (for example, tetrachloroisophthalonitrile), leads to increased exposure. In addition, European Patent EP 337103 describes an anti-bioorganism control agent comprising at least one imidazole compound similar in structure to the imidazole used as an active ingredient in the present invention and at least one active ingredient selected from cyanoacetamides, chlorine-containing organic compounds (including tetrachloroisophthalonitrile), phenylamides (including methyl-N- (2-methoxyacetyl) -N- (2,6-xylyl) -DL-alaninate), derivatives of cinnamic acid, copper compounds and organophosphorus compounds (including fosetylaluminium).

 Considering these patents from the point of view of the present invention, it should be noted that they do not describe or offer combinations of imidazoles as active ingredients (a) and inorganic compounds of phosphorus, β-methoxyacrylates or oxazolidinediones. They do not describe or imply a clearly superior suppressive effect that a composition may have, containing as an active ingredient an imidazole compound and, as another active ingredient, at least one of a compound selected from the group consisting of cyanoacetamide, an organic chlorine-containing compounds, phenylamide, cinnamic acid compounds, copper compounds and organophosphorus compounds.

 As for the combination of the active ingredient (a) and the activity enhancing ingredient (c) (described later), European patent EP 298196 describes the usefulness of the imidazole of the present invention as an agent for controlling harmful bioorganisms, and it is indicated that this compound can be incorporated into compositions various forms together with adjuvants. JP-A-Heisei-3-11003 (the term “JP-A” as used herein means “unexamined published Japanese patent application”) describes a method for controlling harmful bio-organisms, including the use of an aqueous dispersion containing at least , one imidazole compound of the present invention and a surfactant is an ester of sorbitan and a higher fatty acid.

 The imidazole compound represented by the formula (I) and many other conventional means for controlling harmful bioorganisms possess certain inhibitory characteristics. Some of them have insufficient inhibitory effect on some harmful bioorganisms or some are less effective in treatment than in prophylaxis, or some have a relatively short duration of residual action. Therefore, sometimes there are cases in which their inhibitory effect on harmful bioorganisms is insufficient in a number of practical uses. In addition, although the imidazole compound of formula (I) exhibits an excellent fungicidal effect on ficomycetes, it tends to weaken the therapeutic and / or prophylactic effect depending on the state of development of the disease. From this point of view, increased action is also desirable.

 On the other hand, in the practical use of a harmful bioorganism control agent containing an imidazole compound of the formula (I), it is desirable to minimize the amount of the compound used for cost reasons and at the same time try to deal with as many harmful bioorganisms as possible, time of their manifestation or time of occurrence of the disease. In addition, although an agent for controlling harmful bio-organisms containing an imidazole derivative of the formula (I) as an active ingredient is particularly excellent in relation to a prophylactic effect, an enhancement of its therapeutic effect is required.

Description of the invention
The inventors of the present invention conducted studies to solve the above problems and as a result found that the imidazole compound of formula (I) as the active ingredient (a) and the specific compound as the active ingredient (b) give unexpected results, for example, such that the relative amounts of the compounds can be reduced or expand the corresponding spectrum of inhibitory action compared to using them individually. The authors also found that the combined use of the active ingredient (a) with the activity enhancing ingredient (c) leads to a marked increase in the inhibitory effect, in particular the therapeutic effect, compared to the use of the active ingredient (a) alone, due to which it is possible to reduce the amount of active ingredient (a). The present invention is implemented based on these findings.

где R представляет низшую алкильную группу или низшую алкоксигруппу и
n представляет целое число от 1 до 5,
в качестве активного ингредиента и
(b) по меньшей мере, одно неорганическое соединение фосфора и/или, по меньшей мере, один фунгицид для фикомицетов в качестве активного ингредиента или
(c) спредер в качестве усиливающего активность ингредиента.The present invention relates to a composition for controlling harmful bio-organisms containing
(a) at least one imidazole compound represented by formula (I)

where R represents a lower alkyl group or lower alkoxy group and
n represents an integer from 1 to 5,
as an active ingredient and
(b) at least one inorganic phosphorus compound and / or at least one phycomycete fungicide as an active ingredient; or
(c) a spreader as an activity enhancing ingredient.

Best Practices for Carrying Out the Invention
In formula (I), the lower alkyl group or the lower alkoxy group represented by R is an alkyl group of 1 to 6 carbon atoms, such as methyl, ethyl, propyl, butyl, pentyl or hexyl, which may have a linear or branched chain. When n is 2 or more, R may be the same or different.

The imidazole compounds represented by the formula (I) include the following compounds:
4-chloro-2-cyano-1-dimethylsulfamoyl-5- (4-methylphenyl) imidazole (compound 1);
4-chloro-2-cyano-1-dimethylsulfamoyl-5- (4-methoxyphenyl) imidazole (compound 2);
4-chloro-2-cyano-1-dimethylsulfamoyl-5- (4-ethylphenyl) imidazole (compound 3) and
4-chloro-2-cyano-1-dimethylsulfamoyl-5- (3-methyl-4-methoxyphenyl) imidazole (compound 4).

 The imidazole derivatives of formula (I) can be obtained by known methods described, for example, in European patent EP 298196 or in EP-A-705823.

 Inorganic phosphorus compounds, as the active ingredient (b), include phosphoric acid, phosphorous acid, hypophosphorous acid, condensed phosphoric acid, condensed phosphorous acid and their salts. Salts include salts of light metals (with a specific gravity of less than 4), such as alkali metals, alkaline earth metals, aluminum and the like; heavy metals (with a specific gravity of 4 or more), such as zinc, copper, nickel, manganese, etc., and substituted or unsubstituted ammonium salts.

 Salts of phosphoric acid include primary phosphates (e.g. sodium dihydrogen phosphate, potassium dihydrogen phosphate, aluminum dihydrogen phosphate, ammonium dihydrogen phosphate), secondary phosphates (e.g. disodium hydrogen phosphate, dipotassium hydrogen phosphate, triphosphate, dimethyl phosphate, dimethyl phosphate , aluminum phosphate, ammonium phosphate, ammonium magnesium phosphate, magnesium phosphate, calcium phosphate).

 Salts of phosphorous acid include primary or secondary phosphites (e.g., primary or secondary sodium phosphite, primary or secondary potassium phosphite, primary or secondary calcium phosphite).

 Hypochlorous acid salts include sodium hypophosphite, barium hypophosphite and calcium hypophosphite.

 Condensed phosphoric acids and their salts include polyphosphoric acids (e.g., pyrophosphoric acid) and polyphosphates (e.g., sodium pyrophosphate, calcium pyrophosphate, disodium dihydropyrophosphate).

 Condensed phosphorous acids and their salts include polymetaphosphoric acids (e.g. trimethaphosphoric acid, tetramethaphosphoric acid) and polymetaphosphates (e.g. sodium trimetaphosphate, sodium tetramethaphosphate, sodium hexametaphosphate).

Phycomycete fungicides that can be used as the active ingredient (b) include
β-methoxyacrylates
(e.g. methyl- (E) -2- {2- [6- (2-cyanophenoxy) pyrimidin-4-yloxy] phenyl} -3-methoxyacrylate,
methyl- (E) -methoxyimino [α- (o-tolyloxy) -O-tolyl] acetate);
oxazolidinediones
(e.g. 3-anilino-5-methyl-5- (4-phenoxyphenyl) -1,3-oxazolidine-2,4-dione);
cyanoacetamides
(for example, 1- (2-cyano-2-methoxyiminoacetyl) -3-ethylurea (the trivial name is cymoxanil));
chlorine-containing organic compounds
(e.g. tetrachloroisophthalonitrile (trivial name chlorothalonil),
pentachloronitrobenzene (trivial name quintozene));
phenylamides
(e.g. methyl-N- (2-methoxyacetyl) -N- (2,6-xylyl) -DL-alaninate (trivial name is metalaxyl),
2-methoxy-N- (2-oxo-1,3-oxazolidin-3-yl) aceto-2 ', 6'-xylidide (trivial name is oxadixyl),
(±) -α-2-chloro-N- (2,6-xylylacetamide) -γ-butyrolactone (trivial name Ofuras),
methyl-N-phenylacetyl-N- (2,6-xylyl) -DL-alaninate (trivial name benalaxyl),
methyl N- (2-furoyl) -N- [2,6-xylyl) -DL-alaninate (trivial name furalaxyl),
(±) -α- [N- (3-chlorophenyl) cyclopropanecarboxamide] -γ-butyrolactone (the trivial name is ciprofuram));
cinnamic acid compounds
(for example, (E, Z) -4- [3- (4-chlorophenyl) -3- (3,4-dimethoxyphenyl) acryloyl] morpholine (the trivial name is dimethomorph));
copper compounds
(e.g., organic or inorganic copper-containing fungicides) and
organophosphorus compounds
(e.g. tris (ethylphosphonate) aluminum (trivial name fosetylaluminum),
O-2,6-dichloro-p-tolyl-O, O-dimethylphosphorothioate (the trivial name is tolclofosmethyl),
(R, S) -S- (R, S) -s-butyl-O-ethyl-2-oxo-2-thiazolidinylphosphonothioate,
S-benzyl-O, O-diisopropylphosphorothioate (trivial name iprobenfos),
O-ethyl-S, S-diphenylphosphordithioate (trivial name edifenphos),
ethyl 2-diethoxythiophosphoryloxy-5-methylpyrazolo (1,5-a) pyrimidine-6-carboxylate (trivial name pyrazophos)).

 Of the listed compounds (E) -2- {2- [6- (2-cyanophenoxy) pyrimidin-4-yloxy] phenyl} -3-methoxyacrylate (hereinafter referred to as “compound (a)”), methyl- (E) - methoxyimino [α- (o-tolyloxy) -O-tolyl] acetate (hereinafter referred to as “compound (b)”) and 3-anilino-5-methyl-5- (4-phenoxyphenyl) -1,3-oxazolidin-2 , 4-dione (hereinafter referred to as “compound (s)”) are described in Brighton Crop Prot. Conf. Pests and Diseases, p. 435-443 (1992), ibid., P. 403-410 (1992) and ibid., P. 21-26 (1996), respectively.

 Of the above-described organic chlorine compounds, tetrachloroisophthalonitrile is preferred. Of the phenylamides, methyl-N- (2-methoxyacetyl) -N- (2,6-xylyl) -DL-alaninate is preferred. Of the organophosphorus compounds, tris (ethylphosphonate) aluminum is preferred. Of the copper compounds, inorganic copper-containing fungicides are preferred.

 The inorganic or organic copper-containing fungicides mentioned above include fungicidal preparations containing, in addition to the copper compound, chemicals other than the active ingredients (a) and (b) (such as fungicides and the like).

 Inorganic copper-containing fungicides include fungicides containing copper oxysulfate as the active ingredient, such as Sanpun Bordeaux (trademark, manufactured by Dai-ichi Noyaku K.K. and Hokko Chemical Industry Co., Ltd.) and dust Sanlun Bordeaux DL (trademark , manufactured by Dai-ichi Noyaku K.K. and Hokko Chemical Industry Co., Ltd.); fungicides containing copper (I) oxychloride as an active ingredient, such as San Bordeaux (trademark, manufactured by Sankei Chemical Co., Ltd.), Doitsu Borudo A (trademark, manufactured by Dai-ichi Noyaku K.K. and Hokko Chemical Industry Co., Ltd.), Do-cal wettable powder (trademark, manufactured by Yashima Chemical Industry Co., Ltd.), Do-jet (trademark, manufactured by Nissan Chemical Industries, Ltd.), etc .; fungicides containing copper hydroxide as an active ingredient, such as Kocide Bordeaux, Kocide DF, Kocide SD (trademarks, all manufactured by Griffin) and the like, and fungicides containing anhydrous copper (II) sulfate, such as Gandie wettable powder (trademark manufactured by Agro-Kanesho Co., Ltd.), etc.

 Fungicidal preparations containing inorganic copper-containing fungicide and chemicals (such as fungicides and the like) other than ingredients (a) and (b) include a Bordeaux mixture containing basic copper-calcium sulfate; fungicides containing copper and sulfur, such as Engei Bordeaux (trademark, manufactured by Sankei Chemical Co., Ltd.) and the like; fungicides containing copper and validamycin; fungicides containing copper, validamycin and phthalide; fungicides containing copper and pyrifenox; fungicides containing copper (I) and vinclozolin; fungicides containing copper and phthalide; fungicides containing copper and procymidone, such as Scletane wettable powder (trademark, manufactured by Hokko Chemical Industry Co., Ltd.); wettable powders containing copper (I) and fosetil; fungicides containing copper and metalaxyl, such as Ridomil Copper wettable powder (trademark, manufactured by Nihon Nohyaku Co., Ltd.); fungicides containing iprodion and copper (I), such as Daisedo wettable powder (trademark, manufactured by Yashima Chemical Industry Co., Ltd.); fungicides containing iminoctadine triacetate and copper; fungicides containing oxadixyl and copper (I); fungicides containing oxolinic acid and copper; fungicides containing kazugamycin and copper, such as 3DL dust Kasumin Bordeaux (trademark, manufactured by Hokko Chemical Industry Co., Ltd.), Kasumin Bordeaux (trademark, manufactured by Dai-ichi Noyaku K.K. and Hokko Chemical Industry Co., Ltd.), etc .; fungicides containing dithianon and copper (I); fungicides containing streptomycin and copper, such as Do-Stomy wettable powder (trademark, manufactured by Ninon Nohyaku Co., Ltd.) and the like; fungicides containing sodium bicarbonate and copper, such as G-Fine wettable powder (trademark, manufactured by Yashima Chemical Industry Co., Ltd.), and fungicides containing copper and organo-copper compounds, such as Ohu Bordeaux (trademark, manufactured by Sankyo Co ., Ltd.), Kinset wettable powder (trademark, manufactured by Agro-Kanesho Co., Ltd), Kinset 80 wettable powder (trademark, manufactured by Agro-Kanesho Co., Ltd), etc.

 Of these fungicides containing inorganic copper compounds, it is particularly preferred to use fungicides containing one or more active ingredients selected from the group consisting of copper hydroxide, copper oxysulfate, copper oxychloride, anhydrous copper (II) sulfate and basic copper-calcium sulfate.

 Organic copper-containing fungicides include fungicides containing 8-hydroxyquinoline and copper, such as Quinone-do 40 or 80 wettable powder (trademark, manufactured by Agro-Kanesho Co., Ltd), Quinone-do granules (trademark, manufactured by Agro-Kanesho Co ., Ltd), Quinone-do fluid wettable powder (trademark, manufactured by Agro-Kanesho Co., Ltd), Oxine-copper (I) wettable powder (trademark, manufactured by Tomono Agrica Co., Ltd.), Oxine wettable powder -copper (I) 75 (trademark, manufactured by Tomono Agrica Co., Ltd.), wettable powder Oxine-copper (I) 80 (trademark, manufactured by Tomono Agrica Co., Ltd. and Nissan Chemical Industries, Ltd.), Oxine-copper (I) wettable powder (trademark, manufactured by Tomono Agrica Co., Ltd., and Nissan Chemical Industries, Ltd.), Dokirin 80 wettable powder (trademark, manufactured Nihon Nohyaku Co., Ltd.) and Dokirin Fluid Wettable Powder (trademark manufactured by Nihon Nohyaku Co., Ltd.) and the like; copper hydroxynonylbenzenesulfonate fungicides, such as Yonepon (trademark manufactured by Yonezawa Kagaku K.K.) and the like; copper (II) bis (ethylenediamine) bis (dodecylbenzenesulfonate) fungicides, such as Sanyol (trademark manufactured by Otsuka Chemical Co., Ltd., and Yonezawa Kagaku K.K.) and the like, and fungicides based copper terephthalate.

 Fungicidal preparations containing a copper-organic fungicide and fungicides other than ingredients (a) and (b) include fungicides containing iprodion (I) and a copper-organic compound, fungicides containing oxolinic acid and a copper-organic compound, fungicides containing captan (I), thiuram and a copper-organic compound, fungicides containing captan (I) and a copper-organic compound, and fungicides containing a copper-organic compound and dithianone (I), fungicides containing streptomycin and a copper-organic compound, thia fungicides endazol (I) and compound organocopper fungicides containing fenarimol (I) and compound organocopper fungicides, machine oil containing organocopper compound, and fungicides containing guazatine iminoctadine (I) and organocopper compound.

 A distribution agent (spreader) is used as an activity enhancing ingredient (c). Examples of a spreader for use in the present invention are surfactants (excluding sorbitan esters and higher fatty acids), paraffin oil, animal and / or vegetable oil and mineral oil. In general, spreaders are not categorized quite definitely. Some of the animal and / or vegetable oils and mineral oil serve as surfactants, and there are a number of spreaders called binders that cannot be clearly classified. Any spreader that appreciably improves the physical properties of the imidazole derivative of formula (I), such as fixing properties, permeability, ability to apply and flood stomata, enhancing the action of the compound, can be used in the present invention. As a rule, the physical properties of the imidazole of formula (I) could be improved using a spreader and such an effect was obtained that an equivalent inhibitory effect on bioorganisms is obtained with a smaller amount of compound. Of the spreaders described above, surfactants (excluding sorbitan esters and higher fatty acids), animal and / or vegetable oil and mineral oil are preferred. Non-ionic surfactants (with the exception of sorbitan esters and higher fatty acids), animal and / or vegetable oil and mineral oil are preferred.

 Suitable non-ionic surfactants that can be used as the enhancing activity of ingredient (c) include polyoxyethylene alkyl ethers, polyoxyethylene alkyl phenyl ethers, polyoxyethylene aryl ethers, polyoxyethylene glycol alkyl ethers, polyoxyethylene fatty acid esters, polyoxyethylene polyol fatty acid esters, fatty acid amines, -N-oxides such as Aromox C / 12W (trademark, manufactured by Akzo Chemie), polyoxyethylene alkylamines, glyceryl esters rina fatty acids, silicone surfactants, polyoxyethylene surfactants tioefirpolifosfaty such as Reider (trade mark, produced American Trading Company), higher alcohol esters, and sulfuric acid, and dialkyl sulfosuccinates. Among them, polyoxyethylene alkyl esters, polyoxyethylene alkyl phenyl esters, polyoxyethylene fatty acid esters, polyoxyethylene fatty acid esters, silicon-containing surfactants, higher alcohol and sulfuric acid esters and dialkyl sulfosuccinates are preferred. Silicon-containing surfactants, polyoxyethylene alkyl phenyl esters and polyoxyethylene fatty acid esters are more preferred. Silicon-containing surfactants are particularly preferred, in particular DyneAmic (trademark, manufactured by Setre Chemical), KINETIC (trademark, manufactured by Setre Chemical), SILWETT L-77 (manufactured by Witco) and SLIPPA (manufactured by Interagro).

 Specific examples of preferred nonionic surfactants are given in table 1. In addition, applicable nonionic surfactants include polyoxyethylene polysilane ether (a type of silicon-containing surfactant), Renex 36 (trademark, polyoxyethylene alkyl ether manufactured by Wauer AG), Crop Oil Extra (trademark, polyoxyethylene alkylphenyl ether manufactured by Kalo, Inc.), Ortho X-77 carrier (trademark, manufactured by Chevron Chemical Company) and COOP wetting agent (trademark, manufactured by Formland In dustry).

 Suitable anionic surfactants that can be used as an activity enhancing ingredient (c) include sulfuric acid esters such as alkyl sulfoesters, or salts thereof; sulfonic acid surfactants such as naphthylmethanesulfonates and ligninsulfonates; fatty acid salts and fluorine-containing surfactants, with sulfuric acid esters and sulfonic acid derivatives being preferred. Examples of preferred anionic surfactants are shown in table 2.

 Suitable cationic surfactants that can be used as an activity enhancing ingredient (c) are dialkylammonium salts, such as NEEDS (trademark, manufactured by Kao Corporation), and alkyl ammonium salts, such as Arguard T / 50 (trademark, manufactured by Akzo Chemical) are shown in table 3.

 Liquid animal fat and / or vegetable oil that can be used as an activity enhancing ingredient (c) includes vegetable oil, such as corn, soybean oil, linseed oil, sunflower oil, cottonseed oil and rapeseed oil, and liquid animal fat, such as beef tallow and whale tallow. They also include alkylated (e.g. methylated) vegetable oil, such as SCOIL (manufactured by MVRC). Specific examples of suitable animal fat and / or vegetable oil are given in table 4. Among them, preferably vegetable oil.

 Paraffin oil, which can be used as an activity enhancing ingredient (c), includes a product obtained from animal fat and / or vegetable oil, a product obtained from mineral oil (e.g. oil) and mixtures thereof. Specific examples are given in table 5.

 Mineral oil, which can be used as an activity enhancing ingredient (c), includes engine oil, liquid fuel, and silicone oil. Examples of preferred types of mineral oil are given in table 6. Of these, ISHIOIL (manufactured by Ishihara Sangyo Kaisha, Ltd.) is most preferred.

 The spreaders described above, i.e. surfactants (excluding sorbitan esters and fatty acids), animal fats and / or vegetable oils, paraffin oil, mineral oil and the like, can be suitably combined for use in as an activity enhancing ingredient (c). Combinations of two or more distributing agents include a vegetable oil containing surfactants such as Soy Dex (Helena Chemical Company) and the like, and a paraffin oil containing surfactants such as Oleo DP 11E (EI du Pont), Fysol 11E (Schering Agrochemicals), Agri Dex (Helena Chemical Co.), Atplas 411 (ICI Agrochemicals), Herbimax (Love Land Industries, Inc.), Competitor corn oil concentrate (Red Pancer Chemical), Actipron (Oil Co .), DASH (BASF AG), Atlas Adherb (Atlas Interlates, Ltd), Cropspray (Tribart Farm Chemical), Agravia 11E (Wakker Chemie), Penetrator (Helena Chemical Co.), Atlus Adjuvant Oil (Atlus Intertates, Ltd.) etc. They also include mixed spreading agents, listed in table 7.

 As indicated above, in the present invention, in order to enhance the action of the compound, any spreader can be used if it substantially improves the physical properties of the imidazole compound of formula (I), whatever form it may be. Specific examples of distribution agents that cannot be assigned to any of the classes described above are shown in Table 8. It is expected that a composition for controlling harmful bio-organisms containing at least one imidazole of formula (I) as an active ingredient, and included a spreader therein, useful as an activity enhancing ingredient (c), in the ratio of the present invention, will exhibit a similar effect.

 The fungicides described above as active ingredient (b) for phycomycetes have one or more of the following properties: prophylactic effect, therapeutic effect and permeability. Some of the inorganic phosphorus compounds as active ingredient (b), which are not fungicides, like fungicides for phycomycetes, have one or more properties such as prophylactic effect, therapeutic effect and permeability.

 The term "prophylactic fungicides" means that fungicides have the ability to prevent plant diseases. Examples of such fungicides are β-methoxy acrylates, oxazolidinediones, cyanoacetamides, organic chlorine compounds, phenylamides, cinnamic acid derivatives, copper compounds and organophosphorus compounds.

 The term "therapeutic fungicides" means that fungicides can penetrate the body of a plant to combat the invading harmful bio-organisms. Examples of such fungicides are β-methoxyacrylates, cyanoacetamides, phenylamides, cinnamic acid derivatives and organophosphorus compounds.

 The term "permeable fungicides" means that fungicides have the ability to penetrate through the surface of the leaves inside. Examples of such fungicides are (β-methoxy acrylates, oxazolidinediones, cyanoacetamides, phenylamides, cinnamic acid derivatives and organophosphorus compounds.

 In addition to these fungicides, other fungicides for phycomycetes, which have at least one of such properties as a prophylactic effect, therapeutic effect or permeability, are also expected to produce the same effect as observed in the present invention. For example, dithiocarbamate-based fungicides can be mentioned as an example of fungicides for phycomycetes having only a prophylactic effect.

 Compositions for controlling harmful bioorganisms of the present invention, containing at least one imidazole of formula (I) as the active ingredient (a) and at least one inorganic phosphorus compound as the active ingredient (b), are particularly suitable for agricultural and horticultural applications. Specifically, they exhibit excellent action against crop plant diseases, such as rice pyricularia caused by Pyricularia oryzae, rice rhizoctoniosis caused by Rhizoctonia solani, cucumber anthracnose caused by Colletotrichum lagenarium, real powdery mildew of cucumbers caused by Sphaerotheca cuciniformes caused by Pseudoperonospora cubensis, late blight of tomatoes caused by Phytophthora infestans, brown blotch of tomatoes caused by Alternaria solani, citrus melanosis caused by Diaporthe citri, peppermint mold caused by Penicillium digitatum, pear scab, yzvannaya Venturia nashicola, apple alternarioznaya blotch caused by Alternaria mali, grape downy mildew caused by Plasmopara viticola, gray mold caused by Botrytis cinerea, Blight caused by Sclerotinia sclerotiorum, and disease caused by rust fungus, etc. and with soil borne diseases caused by phytopathogenic fungi such as Fusarium, Pythium, Rhizoctonia, Verticillium and Plasmodiophora and the like. In particular, the compositions of the present invention exhibit excellent action in the fight against diseases such as potato late blight caused by Phytophthora infestans, sweet pepper late blight caused by Phytophthora capsici, common watermelon rot caused by Phytophthora drechsleri, late blight of Phytophthora stem, and tobacco stem. nicotianae, tomato late blight, caused by Phytophthora infestans, powdery mildew of cucumbers or watermelon, caused by Pseudoperonospora cubensis, powdery mildew of cabbage or Chinese cabbage, caused by Peronospora brassicae, false powdery mildew of onion, Pharatoproera deropora, piroduroperopora, Perona leoprorora perora, porri, and brown rot of watermelon ordinary, caused by Phytophthora capsici, and downy mildew of grapes caused by Plasmopara viticola and various diseases transmitted through the soil, caused, for example, Aphanomyces, Pythium. The compositions have a long residual effect and exhibit, in particular, an excellent therapeutic effect. Therefore, it is possible to fight diseases by treatment after infection. In addition, since the compositions have systemic activity, it is possible to combat diseases of the stems and foliage through soil cultivation.

 Compositions for controlling harmful bioorganisms of the present invention, containing at least one compound of imidazole of formula (I) as the active ingredient (a) and fungicide for phycomycetes as the active ingredient (b), have excellent fungicidal activity when applied to cultural plants, for example fruit vegetables (for example, cucumbers, tomatoes, eggplants, etc.); cereals (e.g. rice, wheat, etc.); seed vegetable crops; fruits (e.g. apples, pears, grapes, citrus fruits, etc.); potatoes and the like that are infected, or are thought to be infected, by pathogenic fungi. They exhibit excellent suppressive effects in diseases such as powdery mildew, downy mildew, anthracnose, gray rot, cough, mold sclerotia, scab, alternating spotting, bacterial spotting, black spotting, melanosis, glomerellous rottenness, rottenness, fit pyriculariosis, rhizoctoniosis, blackleg, southern sclerotic rot, etc. The compositions also exhibit an excellent suppressive effect in diseases transmitted through the soil caused by phycomycetes such as Pythium and other plant pathogens such as Fusarium, Rhizoctonia, Verticillium, Plasmodiophora and the like. The compositions have a long residual effect and exhibit, in particular, an excellent therapeutic effect. Therefore, it is possible to fight diseases by treatment after infection. In addition, since the compositions have systemic activity, it is possible to combat diseases of the stems and foliage through soil cultivation.

In particular, compositions containing at least one imidazole compound of the formula (I) as an active ingredient (a) and a copper compound and / or an organophosphorus compound as a fungicide for phycomycetes as an active ingredient (b) are especially useful for rural household and gardening. Specifically, the compositions exhibit excellent action against crop plant diseases such as rice pyriculariasis caused by Pyricularia oryzae, rice rhizoctoniosis caused by Rhizoctonia solani, cucumber anthracnose caused by Colletotrichum lagenarium, cucumber powdery mildew, Sphaerothera cucumis, Sphaerotheca caused by Pseudoperonospora cubensis, late blight of tomatoes caused by Phytophthora infestans, brown spotting of tomatoes caused by Alternaria solani, citrus melanosis caused by Diaporthe citri, benchmark citrus mold caused by Penicillium digitatum, scab Ruschi caused by Venturia nashicola, apple alternarioznaya blotch caused by Alternaria mali, grape downy mildew caused by Plasmopara viticola, gray mold caused by Botrytis cinerea, Blight caused by Sclerotinia sclerotiorum, rust, bacterial spot, etc, and
with soil borne diseases caused by phytopathogenic fungi, such as Fusarium, Pythium, Rhizoctonia, Verticillium and Plasmodiophora, etc. In particular, the compositions of the present invention exhibit excellent control against diseases such as late blight of potato or tomato caused by Phytophthora infestans, cucumber downy mildew caused by Pseudoperonospora cubensis, grape downy mildew caused by Plasmopara viticola, and various soil borne diseases caused by phycomycetes such as Plasmodiophora, Aphanomyces, Pythium and the like.

 The compositions of the present invention have a long residual effect, so that they exhibit an excellent prophylactic effect, and also exhibit an excellent therapeutic effect. Therefore, it is possible to fight diseases by treatment after infection. In addition, since they have systemic activity, it is also possible to combat diseases of the stems and foliage by cultivating the soil.

 In particular, compositions containing a copper compound as a fungicide for phycomycetes exhibit an excellent prophylactic effect, and compositions containing an organophosphorus compound as a fungicide for phycomycetes exhibit an excellent therapeutic effect.

 Pest control compositions containing at least one imidazole compound of formula (I) as active ingredient (a) and a cyanoacetamide, phenylamide or cinnamic acid compound as fungicide for phycomycetes as active ingredient (b) exhibit an excellent inhibitory action for diseases caused by ficomycetes, such as plant diseases, such as downy mildew of cucumbers, watermelons, cabbage, Chinese cabbage, onions, pumpkin and grapes; late blight of potato, red pepper, sweet pepper, watermelon ordinary, pumpkin, tobacco and tomatoes; shiroiro-eki-byo onions; brown rot of ordinary watermelon; diseases transmitted through soil caused by fungi pathogenic for plants, such as Pythium and the like. They also have an excellent effect on the control of diseases caused by Plasmodiophora.

 Compositions for controlling harmful bio-organisms containing at least one compound of imidazole of formula (I) as the active ingredient (a) and a compound of β-methoxy acrylate, oxazolidinedione or a chlorine-containing organic compound as fungicide for phycomycetes as the active ingredient (b), exhibit an excellent inhibitory effect against diseases caused by ficomycetes, such as plant diseases, for example rice pyricularosis; rice rhizoctoniosis; anthracnose of cucumbers; downy mildew of cucumbers, watermelons, cabbage, Chinese cabbage, onions, pumpkin and grapes; powdery mildew of wheat, barley and cucumbers; late blight of potato, red pepper, sweet pepper, watermelon ordinary, pumpkin, tobacco and tomatoes; wheat Septoria, brown spotting of tomatoes; citrus melanosis; cherries mold citrus; pear scab; alternative spotting of the apple tree; shiroiro-eki-byo onions; brown rot of ordinary watermelon; various diseases, such as gray rot, sclerotic rot, rust, and bacterial spotting; various diseases transmitted through soil caused by fungi pathogenic for plants, etc., such as Fusarium, Pythium, Rhizoctonia, Verticillium and the like. They also exhibit superior suppressive effects in diseases caused by Plasmodio-phora. The compositions show a particularly excellent suppressive effect in diseases such as late blight of potatoes, red pepper, sweet pepper, watermelon, pumpkin, tobacco, tomatoes, etc., and downy mildew of cucumbers, watermelons, cabbage, Chinese cabbage, onions, pumpkins, grapes, etc.

 In addition, compositions containing the active ingredients (a) and (b) of the present invention show an excellent inhibitory effect against insects harmful to agriculture and horticulture, such as delphacids (Delphacidae), cabbage moth (Plutella xylostella), rice circad (Nephotettix cincticeps), adzuki bean kernel (Callosobruchus chinensis), scoop (Spodoptera litura), aphid peach (Myzus persicae), etc .; mites, such as the two-spotted spider mite (Tetranychus uriticae), carmine spider mite (Tetranychus cinnabarinus), red citrus mite (Ranochny citri), etc., and nematodes such as the southern gall nematode (Meloidogyne inc.

 Compositions for controlling harmful bioorganisms containing the active ingredient (a) and the activity enhancing ingredient (c) of the present invention are particularly suitable for use in agriculture and horticulture. Harmful bioorganisms that can be controlled with these compositions include plant pathogenic fungi that cause plant diseases, such as rice pyriculariosis, rice rhizoctoniosis; anthracnose of cucumbers; powdery mildew of cucumbers; downy mildew of cucumbers, watermelon, cabbage, Chinese cabbage, onions and grapes; late blight of potato, red pepper, sweet pepper, ordinary watermelon, pumpkin, tobacco; late blight of tomatoes; brown spotting of tomatoes; citrus melanosis; cherries mold citrus; pear scab; alternative spotting of the apple tree; various diseases such as gray rot, sclerotic rot, rust, and the like; soil containing pathogenic fungi that cause various plant diseases, such as Fusarium, Pytchium, Rhizoctonia, Verticillium, Plasmodiophora, etc. insects such as dolphacids, cabbage moth, rice cicadas, bean kernels, scoops, peach aphids, etc .; mites, such as two-spotted spider mites, carmine spider mites, citrus red mites, etc. and nematodes, such as the southern gall nematode, etc. More specifically, they are effective for late blight of potato, red pepper, sweet pepper, watermelon, pumpkin, tobacco and tomatoes, and downy mildew of cucumbers, watermelons, cabbage, Chinese cabbage, onions, pumpkin and grapes. Compositions containing the active ingredient (a) and activity enhancing ingredient (c) have a long residual effect and exhibit not only an excellent prophylactic effect, but also an excellent therapeutic effect. Therefore, it is possible to fight diseases through treatment after infection.

 The active ingredients, including the other pesticides described below, as well as the active ingredients (a) and (b) and the activity enhancing ingredient (c) of the harmful bio-organisms compositions of the present invention, can be incorporated into compositions of various forms, such as concentrates emulsions, dusts, wettable powders, aqueous solutions, granules, suspension concentrates, etc., together with various adjuvants common to agricultural products. The active ingredient (a) (imidazole compound of the formula (I)), the active ingredient (b) and other specific compounds can be mixed and formulated, or each of them can be prepared separately and then mixed together. When used, the drug can be used as such or diluted to a certain concentration with an appropriate diluent, such as water.

 Examples of adjuvants that can be used are carriers, emulsifiers, suspending agents, thickeners, stabilizers, dispersants, wetting agents, with the exception of those that are used as an activity enhancing ingredient (c), surfactants, wetting agents, penetrators, antifreezes, anti-foaming agents, etc. These adjuvants are added accordingly, if necessary.

 Carriers are divided into solid carriers and liquid carriers. Solid carriers include powders of animal and plant origin (e.g., starch, sugar, powdered cellulose, cyclodextrin, activated carbon, powdered soybeans, wheat flour, chaff, wood powders, fish meal, milk powder, etc.), and mineral powders (for example, talc, kaolin, bentonite, bentonitalkylamine complexes, calcium carbonate, calcium sulfate, sodium hydrogen carbonate, zeolite, diatomaceous earth, white carbon black, clay, alumina, silica, sulfur powder, hydrated lime, etc.). Examples of liquid carriers are water, vegetable oils (e.g. soybean oil, cottonseed oil), liquid animal fats (e.g. beef tallow, whale oil, etc.), alcohols (e.g. ethanol, ethylene glycol, etc.) ketones (e.g. acetone, methyl ethyl ketone, isobutyl ketone, isophorone, etc.), esters (e.g. dioxane, tetrahydrofuran, etc.), aliphatic hydrocarbons (e.g. kerosene, lighting oil, paraffin oil, etc. ), aromatic hydrocarbons (e.g. toluene, xylene, trimethylbenzene, tetramethylbenzene, cyclohexane, solv nt-naphtha, etc.), halogenated hydrocarbons (e.g. chloroform, chlorobenzene, etc.), acid amides (e.g. dimethylformamide, etc.), esters (e.g. ethyl acetate, fatty acid glycerin esters and the like), nitriles (e.g. acetonitrile, etc.), sulfur-containing compounds (e.g. dimethyl sulfoxide, etc.), N-methyl-2-pyrrolidone, N, N-dimethylformamide and so on. Wetting agents (other than those used as an activity enhancing ingredient (c)) or surfactants include polyoxyethylene sorbitan fatty acid esters.

 In compositions containing at least one imidazole compound of formula (I) as the active compound (a) and at least one inorganic phosphorus compound as the active ingredient (b), the mass ratio of (a) and (b) is usually from 1: 300 to 300: 1, preferably from 1: 100 to 100: 1, more preferably from 1:50 to 5: 1, and most preferably from 1:50 to 1:10.

 In compositions containing at least one imidazole compound of formula (I) as the active compound (a) and at least one fungicide for phycomycetes as the active ingredient (b), the mass ratio of (a) and (b) is usually from 1: 10000 to 10000: 1, preferably from 1: 1000 to 10000: 1, more preferably from 1: 100 to 1000: 1. In particular, in compositions containing at least one imidazole compound of formula (I) as the active compound (a) and at least one cyanoacetamide compound as the active ingredient (b) (fungicide for phycomycetes), the mass ratio (a) and (b) is preferably from 1: 300 to 5: 1. When, in particular, copper compounds and / or organophosphorus compounds are used as the active ingredient (b) (fungicide for phycomycetes), the mass ratio of (a) and (b) is usually from 1: 2000 to 2000: 1, preferably from 1: 300 to 300: 1, more preferably from 1: 100 to 100: 1, and particularly preferably from 1:50 to 5: 1.

 In compositions containing the active ingredient (a) and the activity enhancing ingredient (c), the weight ratio of (a) and (c) is usually from 1: 5000 to 2000: 1, preferably from 0.05: 99.95 to 90 : 10, more preferably 0.2: 99.8 to 80:20.

 A method for controlling harmful bioorganisms using compositions for controlling harmful bioorganisms of the present invention is also included in the scope of the present invention.

 When using harmful bioorganism control compositions containing at least one imidazole compound of formula (I) as active ingredient (a) and at least one inorganic phosphorus compound as active ingredient (b), certain total concentrations for the use of the active ingredients (a) and (b), since they vary depending, for example, on the type of cultivated plant being treated, the processing method, the form of the preparation and the amount of preparation used. For example, the imidazole compound of formula (I) and the inorganic phosphorus compound are used at concentrations from 1 to 1000 ppm and from 1 to 5000 ppm, respectively, when treating foliage and from 10 to 10,000 g / ha and from 10 to 50,000 g / ha respectively, when processing the soil.

 When using compositions for combating harmful bioorganisms containing at least one compound of imidazole of formula (I) as the active ingredient (a) and at least one fungicide for phycomycetes selected from the group consisting of β-methoxyacrylate compound , oxazolidinedione compounds, cyanoacetamide compounds, organic chlorine compounds, phenylamide compounds, cinnamic acid derivatives, as the active ingredient (b), it is not possible to establish certain general concentrations for the use of different ingredients, since they vary depending on the type of fungicide used, the cultivated plant being processed, the processing method, the form of the preparation and the amount of preparation used, the processing schedule and the type of harmful fungus to be controlled. In the case of foliage treatment, for example, the imidazole compound of formula (I) and the fungicide are used at concentrations from 0.01 to 1000 ppm and from 0.01 to 1000 ppm, respectively, preferably from 0.1 to 500 ppm and from 0.1 to 500 ppm, respectively.

 When using harmful bioorganism control compositions containing at least one imidazole compound of formula (I) as the active ingredient (a) and a copper compound and / or organophosphorus compound as the active ingredient (b), certain total concentrations cannot be established for the use of active ingredients, since they vary depending, for example, on the type of fungicide used, the cultivated plant being treated, the processing method, the form of the preparation, the amount of preparation used, raphics processing and form harmful fungi, which are struggling. For example, an imidazole compound of formula (I) and a fungicide are used at concentrations from 0.01 to 1000 ppm and from 1 to 5000 ppm, respectively, when treating foliage and from 10 to 10,000 g / ha and from 10 to 50,000 g / ha respectively, when processing the soil.

 When applying compositions for combating harmful bioorganisms containing the active ingredient (a) and activity enhancing ingredient (c), it is not possible to establish certain general concentrations for the use of these ingredients, since they vary depending, for example, on the type of cultivated plant being treated, the processing method, form of the drug and the amount of drug used. For example, the active ingredient (a) and the activity enhancing ingredient (c) are used at concentrations from 0.1 to 10,000 ppm and from 0.01 to 50 ppm, respectively, when treating foliage and from 0.01 to 100 kg / ha and from 0.1 to 0.5 kg / ha, respectively, when cultivating the soil.

 Compositions containing the active ingredients (a) and (b) can be used as a mixture or in combination, for example, with other pesticides, fertilizers and safeners (safety agents) to enhance the effect. Useful pesticides include bactericides, with the exception of those used as active ingredients (a) and (b), fungicides, insecticides, acaricides, nematicides, antiviral agents, attractants, herbicides and plant growth regulators. In particular, mixtures or combinations of compositions for combating harmful bioorganisms of the present invention and one or more active ingredients from among fungicides other than those used as active ingredients (a) and (b) may have improved properties, in terms of a range of destruction harmful bio-organisms, processing schedules and inhibitory activity against harmful bio-organisms. The imidazole compound of formula (I) as the active ingredient (a), the inorganic phosphorus compound and / or the fungicide for phycomycetes as the active ingredient (b) and the active ingredient (s) from among fungicides other than the active ingredients (a) and ( b), you can enter into separate formulations and mix when using either one or at least two of them mix and enter into the composition of one drug.

 When at least one imidazole compound of formula (I) as an active ingredient (a) is combined with at least one inorganic phosphorus compound and / or at least one phycomycete fungicide as active ingredient (b), the composition obtained immediately before use exhibits a more enhanced inhibitory effect compared to the previously prepared composition. Therefore, it is suitable that the composition containing the active ingredient (a) and, optionally, various adjuvants, and the composition containing the active ingredient (b) and, if necessary, various adjuvants, are individually packaged and delivered as a preparation in two packages. For example, the active ingredient (a) and the active ingredient (b) can be dissolved in the respective liquid carriers and packaged individually, or the active ingredient (a) and a mixture of the active ingredient (b) and other fungicides are dissolved in the respective liquid carriers and packaged separately.

 In a method for controlling harmful bio-organisms using compositions containing the active ingredient (a) and an activity enhancing ingredient (c), the compositions can be used as a mixture with other pesticides described above, which can cause an increase in action. Typical examples of other beneficial pesticides are azole compounds such as triflumisole (trivial name) and the like; quinoxaline compounds such as quinomethionate (trivial name) and the like; benzimidazole compounds such as benomyl (trivial name), etc .; pyridinamine compounds such as fluazinam (trivial name) and the like; sulfenic acid derivatives such as dichlorofluanide (trivial name) and the like; isoxazole compounds such as hydroxyisoxazole (trivial name) and the like; dicarboxyimide compounds such as procymidone (trivial name) and the like; benzanilide compounds such as flutolanil (trivial name) and the like, and benzamide compounds such as (R, S) -4-chloro-N- [cyano (ethoxymethyl)] benzamide and the like.

 Preferred variants of the compositions for combating harmful bioorganisms in accordance with the present invention, containing the active ingredients (a) and (b), are given below only for purposes of explanation, and not limitation.

 (1) Compositions for controlling harmful bio-organisms, where at least one inorganic phosphorus compound and / or at least one fungicide for phycomycetes have a prophylactic effect.

 (2) Compositions for controlling harmful bio-organisms, where at least one inorganic phosphorus compound and / or at least one fungicide for phycomycetes have a therapeutic effect.

 (3) Compositions for controlling harmful bio-organisms, where at least one inorganic phosphorus compound and / or at least one fungicide for pericomycetes are permeable.

 (4) Compositions for controlling harmful bio-organisms, where at least one inorganic phosphorus compound and / or at least one fungicide for phycomycetes have a prophylactic and therapeutic effect.

 (5) Compositions for controlling harmful bio-organisms, where at least one inorganic phosphorus compound and / or at least one fungicide for phycomycetes have a prophylactic effect and permeability.

 (6) Compositions for controlling harmful bio-organisms, where at least one inorganic phosphorus compound and / or at least one fungicide for phycomycetes have a therapeutic effect and permeability.

 (7) Compositions for controlling harmful bio-organisms, where at least one inorganic phosphorus compound and / or at least one fungicide for phycomycetes have a prophylactic effect, therapeutic effect and permeability.

 (8) Compositions for controlling harmful bioorganisms, wherein the active ingredient (b) is at least one organophosphorus compound.

 (9) Compositions for controlling harmful bio-organisms, wherein the active ingredient (b) is at least one fungicide for phycomycetes.

 (10) Compositions for controlling harmful bioorganisms according to (9), wherein the fungicide for phycomycetes is a compound selected from the group consisting of β-methoxyacrylate compound, oxazolidinedione compound, cyanoacetamide compound, organic chlorine compound, phenylamide compound, cinnamon compound acids, copper compounds and organophosphorus compounds.

 (11) Compositions for controlling harmful bio-organisms according to (9), wherein the fungicide for phycomycetes is a β-methoxy acrylate compound and / or an oxazolidinedione compound.

 (12) Compositions for controlling harmful bioorganisms according to (9), wherein the fungicide for phycomycetes is a compound selected from the group consisting of a cyanoacetamide compound, an organic chlorine compound, a phenylamide compound, a cinnamic acid compound, a copper compound and an organophosphorus compound.

 (13) Compositions for controlling harmful bioorganisms according to claims (9), (10) or (11), where the fungicide for phycomycetes is a β-methoxyacrylate compound.

 (14) Compositions for controlling harmful bioorganisms according to (13), wherein the β-methoxy acrylate compound is methyl- (E) -2- {2- [6- (2-cyanophenoxy) pyrimidin-4-yloxy] phenyl} -3-methoxyacrylate or methyl- (E) -methoxyimino [α- (o-tolyloxy) -O-tolyl] acetate.

 (15) Compositions for controlling harmful bioorganisms according to claims (9), (10) or (11), wherein the fungicide for phycomycetes is an oxazolidinedione compound.

 (16) Compositions for controlling harmful bio-organisms according to (15), wherein the fungicide for phycomycetes is 3-anilino-5-methyl-5- (4-phenoxyphenyl) -1,3-oxazolidine-2,4-dione.

 (17) Compositions for controlling harmful bioorganisms according to claims (9), (10) or (12), wherein the fungicide for phycomycetes is a cyanoacetamide compound.

 (18) Compositions for controlling harmful bioorganisms according to (17), wherein the cyanoacetamide compound is 1- (2-cyano-2-methoxyiminoacetyl) -3-ethylurea.

 (19) Compositions for controlling harmful bioorganisms according to claims (9), (10) or (12), where the fungicide for phycomycetes is an organic chlorine-containing compound.

 (20) Compositions for controlling harmful bio-organisms according to (19), wherein the organic chlorine-containing compound is tetrachloroisophthalonitrile or pentachloronitrobenzene.

 (21) Compositions for controlling harmful bio-organisms according to (19), wherein the organic chlorine-containing compound is tetrachloroisophthalonitrile.

 (22) Compositions for controlling harmful bioorganisms according to claims (9), (10) or (12), where the fungicide for phycomycetes is a phenylamide compound.

 (23) Compositions for controlling harmful biological organisms according to (22), wherein the phenylamide compound is at least one compound selected from the group consisting of methyl-N- (2-methoxyacetyl) -N- (2, 6-xylyl) -DL-alaninate, 2-methoxy-N- (2-oxo-1,3-oxazolidin-3-yl) aceto-2 ', 6'-xylidide, (±) -α-2-chloro- N- (2,6-xylylacetamide) -γ-butyrolactone, methyl-N-phenylacetyl-N- (2,6-xylyl) -DL-alaninate, methyl-N- (2-furoyl) -N- (2,6 xylyl) -DL-alaninate and (±) -α- [N- (3-chlorophenyl) cyclopropanecarboxamide] -γ-butyrolactone.

 (24) Compositions for controlling harmful biological organisms according to (22), wherein the phenylamide compound is methyl-N- (2-methoxyacetyl) -N- (2,6-xylyl) -DL-alaninate.

 (25) Compositions for controlling harmful bio-organisms according to paragraphs. (9), (10) or (12), where the fungicide for phycomycetes is a cinnamic acid compound.

 (26) Compositions for controlling harmful biological organisms according to (25), wherein the cinnamic acid compound is (E, Z) -4- [3- (4-chlorophenyl) -3- (3,4-dimethoxyphenyl) acryloyl] morpholine.

 (27) Compositions for controlling harmful bioorganisms according to claims (9), (10) or (12), wherein the fungicide for phycomycetes is a copper compound and / or an organophosphorus compound.

 (28) Compositions for controlling harmful bio-organisms according to (27), wherein the copper compound is an inorganic copper-containing fungicide and / or organic copper-containing fungicide.

 (29) Compositions for controlling harmful bioorganisms according to (28), wherein the active ingredient of the inorganic copper-containing fungicide is at least one compound selected from the group consisting of copper hydroxide, copper oxysulfate, copper oxychloride, anhydrous copper sulfate (II) and basic copper-calcium sulfate.

 (30) Compositions for controlling harmful bioorganisms according to (27), wherein the organophosphorus compound is at least one compound selected from the group consisting of tris (ethylphosphonate) aluminum, O-2,6-dichloro-p -tolyl-O, O-dimethylphosphorothioate, (R, S) -S- (R, S) -t-butyl-O-ethyl-2-oxo-2-thiazolidinylphosphonothioate, S-benzyl diisopropylphosphorothioate, O-ethyl diphenylphosphorfthioate and ethyl 2 -diethoxythiophosphoryloxy-5-methylpyrazolo (1,5-a) pyrimidine-6-carboxylate.

 (31) Compositions for controlling harmful bio-organisms according to (27), wherein the organophosphorus compound is aluminum tris (ethylphosphonate).

 (32) Compositions for controlling harmful bioorganisms according to (27), wherein the weight ratio of at least one imidazole compound of formula (I) and copper and / or organophosphorus compounds is from 1: 2000 to 2000: 1.

 Preferred uses of the composition comprising the active ingredient (a) and the activity enhancing ingredient (c) to harmful bioorganisms are described below for purposes of explanation only and not limitation.

(1) Compositions containing the active ingredient (a) and activity enhancing ingredient (c) can be applied to harmful bioorganisms in the form of an aqueous dispersion. With this method, an aqueous dispersion is sprayed over places where harmful bio-organisms are found or expected to appear, such as foliage of beneficial plants or soil. Aqueous dispersion is especially effective for application to foliage. An aqueous dispersion is obtained, for example, by:
(i) dispersing the active ingredient preparation in water and adding an activity enhancing ingredient to the resulting dispersion; (ii) dispersing the preparation containing the active ingredient and enhancing the activity of the ingredient in water or by a method similar to (i) or (ii). An aqueous dispersion for use is prepared using 1 liter of water per 0.1-10000 mg of compositions for controlling harmful bioorganisms, so as to obtain a concentration of the active ingredient of 0.1-10000 ppm. The aqueous dispersion is sprayed in an amount of 100 to 10,000 l / ha.

 (2) Compositions containing the active ingredient (a) and the activity enhancing ingredient (c) can be applied in the form of an aqueous suspension in the same manner as in the case of an aqueous dispersion. The concentration of the active ingredient in the aqueous suspension is from 0.1 to 10,000 ppm. The aqueous suspension is sprayed in an amount of from 100 to 10,000 l / ha.

 The following are illustrative examples of test compositions for controlling harmful bioorganisms of the present invention when used as fungicides for agriculture or horticulture.

Test Example 1
Checking the therapeutic effect of false powdery mildew of cucumbers
A composition for controlling harmful bioorganisms containing compound 1 and the inorganic phosphorus compound shown in table 9 at a concentration of 100 ppm and 2000 ppm, respectively, was obtained by mixing an aqueous suspension suspension of compound 1 and a 20% wettable powder of an inorganic phosphorus compound. A wettable 20% powder of an inorganic phosphorus compound was obtained in accordance with the reference composition example given below.

Cucumbers (grade Suyo) were grown in plastic pots (diameter 7.5 cm). When the plant reached the second leaf phase, it was inoculated by suspension of a spore of a fungus causing downy mildew (Pseudoperonospora cubensis). After 24 hours, the plants were sprayed using the spraying apparatus as prepared above (10 ml per pot). For comparison, the same test was carried out using 10 ml of a composition containing 2000 ppm of an inorganic phosphorus compound and not containing compound 1, or 10 ml of a composition containing 100 ppm of a compound 1 and not containing inorganic phosphorus compound. The plants were kept in chambers at 22-24 ^o C for 6 days and the area of damage of the first leaf was measured, the incidence rate (%) was calculated by the results according to the following formula. The results are shown in table 9.

 The incidence rate (%) = (a / b) x 100, where a is the area of damage to the treated plant and b is the area of damage to the control (untreated plant).

The theoretical incidence rate (%) can be calculated using the Colby formula below. In cases where the incidence rate of the test composition is lower than the theoretical coefficient, the test composition may give a synergistic effect. In these cases, the theoretical incidence rate (%) is shown in table 9 in parentheses. Theoretical incidence rate (%) = (X ¹ x Y ¹ ) / 100, where X ¹ is the incidence rate (%) of a plant treated only with compound 1, and Y ¹ is the incidence rate (%) of a plant treated only with inorganic compound phosphorus.

Test Example 2
Checking the therapeutic effect of false powdery mildew of cucumbers
A composition for controlling harmful bioorganisms containing compound 1 at the previously indicated concentration and the inorganic phosphorus compound shown in Table 10 at a concentration of 250 ppm was prepared by mixing an aqueous suspension of compound 1 and a 20% wettable powder of an inorganic phosphorus compound. A wettable 20% powder of an inorganic phosphorus compound was prepared in accordance with the reference composition example given below.

Cucumbers (grade Suyo) were grown in plastic pots (diameter 7.5 cm). When the plant reached the second leaf phase, it was inoculated by suspension of a spore of a fungus causing downy mildew (Pseudoperonospora cubensis). After 24 hours, the plants were sprayed using the sprayer prepared above (10 ml per pot). For comparison, the same test was performed using 10 ml per pot of a composition containing 250 ppm of inorganic phosphorus compound and not containing compound 1, or 10 ml per pot of a composition containing compound 1 at a certain concentration and not containing inorganic phosphorus compound. The plants were kept in chambers at 22-24 ^o C for 4 days and the area of damage of the first leaf was measured, the incidence rate (%) was calculated according to the following formula. The results are shown in table 10.

 The incidence rate (%) = (a / b) x 100, where a is the area of damage to the treated plant and b is the area of damage to the control (untreated plant).

The theoretical incidence rate (%) can be calculated using the Colby formula below. In cases where the incidence rate of the test composition is lower than the theoretical coefficient, the test composition may give a synergistic effect. In these cases, the theoretical incidence rate (%) is shown in table 10 in parentheses. Theoretical incidence rate (%) = (X ² x Y ² ) / 100, where X ² is the incidence rate (%) of a plant treated only with compound 1, and Y ² is the incidence rate (%) of a plant treated only with inorganic compound phosphorus.

Test Example 3
Field tests of the influence of downy mildew of cucumbers
Five pieces of cucumber seedlings (variety Tokiwa Kohai Hikari, 3, type P) were planted in a two-leaf phase (3 m ² each) in a field located in Kusatsu City, Shiqa, Japan, May 10, 1997. A composition containing 50 h / ppm of compound 1 and 1,500 ppm of the inorganic phosphorus compound shown in table 11 were sprayed with a small sprayer in an amount of 500 ml per plot on June 10 and 17. For comparison, the same field test was performed using a composition containing only 1,500 ppm of the inorganic phosphorus compound or a composition containing only 50 ppm of the compound 1. On June 23, all leaves were examined to obtain a suppression index in accordance with the following rating system . The results are shown in table 11. Artificial infection with pathogenic fungi was not performed, so the disease was spontaneous (see table A).

Test Example 4
Checking the therapeutic effect of false powdery mildew of cucumbers
Cucumbers (grade Suyo) were grown in plastic pots (diameter 7.5 cm). When the plant reached the second leaf phase, it was inoculated by suspension of spores of the fungus that caused downy mildew (Pseudorenonosroba subensis). After 24 hours, plants using a spraying device were sprayed with a composition containing the compounds shown in tables 12-19, in the respective indicated concentrations. The plants were kept in chambers at 22-24 ^o C for 6 days and the area of damage of the first leaf was measured, the incidence rate (%) was calculated by the results according to the following formula. The results are shown in tables 12-19.

 The incidence rate (%) = (a / b) x 100, where a is the area of damage to the treated plant and b is the area of damage to the control (untreated plant).

The theoretical incidence rate (%) can be calculated using the Colby formula below. In cases where the incidence rate of the test composition is lower than the theoretical coefficient, the test composition may give a synergistic effect. In these cases, the theoretical incidence rate (%) is shown in tables 12-19 in parentheses. Theoretical incidence rate (%) = (X ³ x Y ³ ) / 100, where X ² is the incidence rate (%) of a plant treated only with compound 1, 2 or 3, and Y ³ is the incidence rate (%) of the plant, treated only with compound (a), i.e. methyl- (E) -2- {2- [6- (2-cyanophenoxy) pyrimidin-4-yloxy] phenyl} -3-methoxyacrylate, compound (b) (i.e. methyl- (E) -methoxyimino [α - (o-tolyloxy) -O-tolyl] acetate), cymoxanyl, metalaxyl or dimetomorph.

Test Example 5
Checking the therapeutic effect of false powdery mildew of cucumbers
Cucumbers (grade Suyo) were grown in plastic pots (diameter 7.5 cm). When the plant reached the second leaf phase, it was inoculated by spraying with a suspension of spores of powdery mildew fungus (Pseudoperonospora cubensis). After 18 hours, two plants were sprayed with a spray device to 20 ml of a composition containing compound 1 and compound (c) (3-anilino-5-methyl-5- (4-phenoxyphenyl) -1,3-oxazolidine-2,4- dione) at the appropriate concentrations indicated in Table 20. The plants were kept in chambers at 22-24 ^o C for 5 days and the average area of damage was measured on two plants, the incidence rate (%) was calculated using the same method as in the test example 1. The results are shown in table 20.

The theoretical incidence rate (%) can be calculated using the Colby formula below. In cases where the incidence rate of the test composition is lower than the theoretical coefficient, the test composition may give a synergistic effect. In these cases, the theoretical incidence rate (%) is shown in table 20 in parentheses. Theoretical incidence rate (%) = (X ⁴ x Y ⁴ ) / 100, where X ⁴ is the incidence rate (%) of a plant treated only with compound 1, and Y ⁴ is the incidence rate (%) of a plant treated only with compound ( from).

Test Example 6
Checking the therapeutic effect of late blight of tomatoes
Tomatoes (cultivar Ponderosa) were grown in plastic pots (diameter 7.5 cm). When the plant reached the fourth leaf phase, it was inoculated by suspension of zoosporangium fungus causing late blight (Phytophthora infestans). After 6 hours, plants using a spraying device were sprayed with a composition (10 ml per pot) containing compound 1 and cymoxanil, metalaxyl or dimetomorph at the appropriate concentrations indicated in tables 21-23. The plants were kept in chambers at 22-24 ^o C for 3-5 days and the area of damage was measured, according to the results, the incidence rate (%) was calculated in the same way as in test example 1. The results are shown in tables 21-23.

 The theoretical incidence rate (%) can be calculated using the Colby formula below. In cases where the incidence rate of the test composition is lower than the theoretical coefficient, the test composition can produce a synergistic effect. In these cases, the theoretical incidence rate (%) is shown in tables 21-23 in parentheses.

Theoretical incidence rate (%) = (X ⁵ x Y ⁵ ) / 100, where X ⁵ is the incidence rate (%) of a plant treated only with compound 1, and Y ⁵ is the incidence rate (%) of a plant treated only with cymoxanil, metalaxyl or dimetomorph.

Test Example 7
Field trials with downy mildew of cucumbers
Seven pieces of cucumber seedlings (variety Tokiwa Kohai Hikari, 3, type P) were planted (5 m ² each) in a field located in Kusatsu City, Shiga, Japan, May 9, 1995. A composition containing compound 1 and chlorothalonil in appropriate concentrations shown in table 24, using a small sprayer sprayed over the plants in the amount of 500-750 ml per plot on May 30 and June 6. On June 14th, all leaves were examined to obtain a suppression index in accordance with the following rating system. The results are shown in table 24. Artificial infection with pathogenic fungi was not performed, so the disease was spontaneous (see table B).

Test Example 8
Checking the preventive effect on downy mildew of cucumbers
Cucumbers (grade Suyo) were grown in plastic pots (diameter 7.5 cm). When the plant reached the second leaf phase, it was sprayed with a spray device on 10 ml of a composition containing compound 1 and Doitsu Borudo A (trademark for wettable powder based on copper oxychloride, manufactured by Hokko Chemical Industry Co., Ltd.) at the appropriate concentrations indicated table 25. After 24 hours, the plant was inoculated with a suspension of spores of the fungus causing downy mildew (Pseudoperonospora cubensis). The plants were kept in chambers at 22-24 ^o C for 6 days and the area of damage of the first leaf was measured, the incidence rate (%) was calculated by the results according to the following formula. The results are shown in table 25.

 The incidence rate (%) = (a / b) x 100, where a is the area of damage to the treated plant and b is the area of damage to the control (untreated plant).

The theoretical incidence rate (%) can be calculated using the Colby formula below. In cases where the incidence rate of the test composition is lower than the theoretical coefficient, the test composition may give a synergistic effect. In these cases, the theoretical incidence rate (%) is shown in table 25 in parentheses. Theoretical incidence rate (%) = (X ⁶ x Y ⁶ ) / 100, where X ⁶ is the incidence rate (%) of a plant treated only with compound 1, and Y ⁶ is the incidence rate (%) of a plant treated only with Doitsu Borudo A.

Test Example 9
Checking the preventive effect of late blight of tomatoes
Tomatoes (cultivar Ponderosa) were grown in plastic pots (diameter 7.5 cm). When the plant reached the fourth leaf phase, the seedlings sprayed 10 ml of a composition containing compound 1 and Kocide Bordeaux (trademark for wettable powder based on copper hydroxide, manufactured by Griffin) or Doitsu Borudo A (trademark for wettable powder based on copper oxychloride) using a sprayer , manufactured by Hokko Chemical Industry Co., Ltd.), at the appropriate concentrations indicated in Tables 26 and 27. After 24 hours, the plants were inoculated by suspension of zoosporangium fungus causing late blight (Phytophthora infestans). The plants were kept in chambers at 22-24 ^o C for 3 days and the area of damage was measured, according to the results, the incidence rate (%) was calculated in the same way as in test example 1. The results are shown in tables 26 and 27.

The theoretical incidence rate (%) can be calculated using the Colby formula below. In cases where the incidence rate of the test composition is lower than the theoretical coefficient, the test composition may give a synergistic effect. In these cases, the theoretical incidence rate (%) is shown in tables 26 and 27 in parentheses. Theoretical incidence rate (%) = (X ⁷ x Y ⁷ ) / 100, where X ⁷ is the incidence rate (%) of a plant treated only with compound 1, and Y ⁷ is the incidence rate (%) of a plant treated only with Kocide Bordeaux or Doitsu Borudo A.

Test Example 10
Checking the therapeutic effect of false powdery mildew of cucumbers
Cucumbers (grade Suyo) were grown in plastic pots (diameter 7.5 cm). When the plant reached the second leaf phase, it was inoculated by suspension of a spore of the fungus causing downy mildew (Pseudoperonospora cubensis). After 24 hours, plants using a spraying device were sprayed with 10 ml of a composition containing compound 1 and tris (ethylphosphonate) aluminum (fosetylaluminium) in the appropriate concentrations indicated in table 28. The plants were kept in chambers at 22-24 ^o C for 6 days and measured the area of damage, the results calculated the incidence rate (%) in the same manner as in test example 1. The results are shown in table 28.

The theoretical incidence rate (%) can be calculated using the Colby formula below. In cases where the incidence rate of the test composition is lower than the theoretical coefficient, the test composition may give a synergistic effect. In these cases, the theoretical incidence rate (%) is shown in table 28 in parentheses. The theoretical incidence rate (%) = (X ⁸ x Y ⁸ ) / 100, where X ⁸ is the incidence rate (%) of a plant treated only with compound 1, and Y ⁸ is the incidence rate (%) of a plant treated only with fosetyl aluminum.

Test Example 11
Checking the therapeutic effect of false powdery mildew of cucumbers
Obtaining an aqueous dispersion
The distribution agent (spreader is an activity enhancing ingredient) shown in Table 29 was diluted with water 500 or 1000 times, compound 1 was added to it at a concentration of 100 ppm or 12.5 ppm and an aqueous dispersion was obtained. For comparison, an aqueous dispersion containing 100 ppm or 12.5 ppm of compound 1 and not containing an activity enhancing ingredient was prepared in the same way.

Test Procedure and Results
Cucumbers (grade Suyo) were grown in plastic pots (diameter 7.5 cm). When the plant reached the second leaf phase, it was inoculated by suspension of a spore of a fungus causing downy mildew (Pseudoperonospora cubensis). After 15-24 hours, an aqueous dispersion of 20 ml per 0.25 m ^{2 was} sprayed over the plants using a spraying device. Plants were kept in chambers at 22-24 ^o C for 4-6 days and the area of damage of the first leaf was measured to obtain a suppression index in accordance with the following rating system (see table B). The results are shown in table 29.

Test Example 12
Checking the therapeutic effect of late blight of tomatoes
Obtaining an aqueous dispersion
The spreader (activity enhancing ingredient) shown in Table 30 was diluted 500 times with water, compound 1 was added thereto at a concentration of 400 ppm or 12.5 ppm and an aqueous dispersion was obtained.

 For comparison, an aqueous dispersion was prepared in the same way, excluding the use of the surface-active sorbitan esters of fatty acids as listed in Table 30 as spreading agents (spreading agents for comparison A, B and C) and adding compound 1 at a concentration of 400 hours / million For another comparison, an aqueous suspension was prepared in the same way containing 400 ppm or 12.5 ppm of compound 1 and not containing an activity enhancing ingredient.

Test Methods and Results
Tomatoes (cultivar Ponderosa) were grown in plastic pots (diameter 7.5 cm). When the plant reached the fourth leaf phase, it was inoculated by spraying with a suspension of the zoosporangium of a fungus that causes late blight (Phytophtora infestans). After 4 hours, the suspension prepared above in the amount of 20 ml per 0.25 m ^{2 was} sprayed over the plant using a spraying device. After the plants were kept in the chambers at 22-24 ^o C for 3 days, the area of damage was measured and the suppression index was calculated according to the same rating system as in test example 11. The results are shown in table 31.

Test Example 13
Checking the therapeutic effect of late blight of tomatoes
Obtaining an aqueous dispersion
The agent-spreader (activity enhancing ingredient) shown in table 32 was diluted 2000 times with water and compound 1 was added to it at a concentration of 100 ppm to obtain an aqueous dispersion. For comparison, an aqueous dispersion containing 100 ppm of compound 1 and not containing an activity enhancing ingredient was prepared in the same manner.

Test Methods and Results
Tomatoes (cultivar Ponderosa) were grown in plastic pots (diameter 7.5 cm). When the plant reached the fourth leaf phase, it was inoculated by suspension of zoosporangium fungus causing late blight (Phytophthora infestans). After 4 hours, the suspension prepared above in the amount of 20 ml per 0.25 m ^{2 was} sprayed over the plants using a spraying device. After the plants were kept in the chambers at 22-24 ^o C for 3 days, the damage area was measured and the suppression index was calculated according to the same rating system as in test example 11. The results are shown in table 32.

Test Example 14
Checking the preventive effect of late blight of tomatoes
Obtaining an aqueous dispersion
Agent-spreader 58 or 91 (activity enhancing ingredient) was diluted 500 times with water and compound 1 was added at the concentration indicated above, and an aqueous dispersion was obtained. For comparison, an aqueous dispersion containing the same amount of compound 1 and not containing an activity enhancing ingredient was prepared in the same manner.

Test Methods and Results
Tomatoes (cultivar Ponderosa) were grown in plastic pots (diameter 7.5 cm). When the plant reached the fourth leaf phase, the suspension prepared above in the amount of 20 ml per 0.25 m ^{2 was} sprayed over it using a spraying device. 24 hours after spraying, the plants for inoculation were sprayed with a suspension of zoosporangia of a fungus causing late blight (Phytophthora infestans), and the plants were kept in chambers at 22-24 ^° C for 3 days. The damage area was measured and the suppression index was calculated according to the results in accordance with the same rating system as in test example 11. The results are shown in table 33.

Test Example 15
Checking the therapeutic effect of false powdery mildew of cucumbers
Obtaining an aqueous dispersion
The distribution agent (activity enhancing ingredient) shown in Table 34 was diluted 500 or 2,000 times with water, compound 1 was added thereto at a concentration of 12.5 ppm to obtain an aqueous dispersion. For comparison, an aqueous dispersion containing 12.5 ppm of compound 1 and not containing an activity enhancing ingredient was prepared in the same manner.

Test Procedure and Results
Cucumbers (grade Suyo) were grown in plastic pots (diameter 7.5 cm). When the plant reached the second leaf phase, it was inoculated by suspension of a spore of a fungus causing downy mildew (Pseudoperonospora cubensis). After 15-24 hours, an aqueous dispersion of 20 ml per 0.25 m ^{2 was} sprayed over the plants using a spraying device. The plants were kept in chambers at 22-24 ^° C for 5 days and the area of damage to the first leaf was measured to obtain the ratio of damaged leaf area to intact (%). The results are shown in table 34.

 Note: all parts in the following examples of compositions 1-14 and in the reference example of the composition are indicated as mass.

Example composition 1, parts by weight:
(1) Compound 1 to 5
(2) Dipotassium hydrogen phosphate - 7
(3) Diatomaceous earth - 82
(4) Dialkyl sulfosuccinate - 2
(5) Polyoxyethylene alkyl phenyl ether sulfate - 4
The above components are mixed until homogeneous and get wettable powder.

Example composition 2, parts by weight:
(1) Compound 1 to 5
(2) Sodium tertiary phosphate dodecahydrate - 16
(3) Diatomaceous earth - 73
(4) Dialkyl sulfosuccinate - 2
(5) Polyoxyethylene alkyl phenyl ether sulfate - 4
The above components are mixed until homogeneous and get wettable powder.

 An example of composition 3, parts by weight

(1) Compound 1 to 5
(2) Dipotassium hydrogen phosphate - 18
(3) Kerosene - 63
(4) Dialkyl sulfosuccinate - 2
(5) a Mixture of a derivative of polyoxyethylene phenyl phenol and polyoxyethylene sorbitan alkylate - 12
The above components are mixed until homogeneous and finely ground to obtain a suspension concentrate.

An example of composition 4, parts by weight:
(1) Kaolin - 78
(2) Condensate of β-naphthalenesulfonate sodium and formaldehyde - 2
(3) Polyoxyethylene alkyl aryl sulfate - 5
(4) Hydrated Amorphous Silica - 15
A mixture of the above components, dipotassium hydrogen phosphate and compound 1 are mixed in a mass ratio of 79: 20: 1 to obtain a wettable powder.

An example of composition 5, parts by weight:
(1) Kaolin - 78
(2) Condensate of β-naphthalenesulfonate sodium and formaldehyde - 2
(3) Polyoxyethylene alkyl aryl sulfate - 5
(4) Hydrated Amorphous Silica - 15
A mixture of the above components, compound 1 and metalaxyl are mixed in a mass ratio of 8: 1: 1 to obtain a wettable powder.

An example of composition 6, parts by weight:
(1) Compound 2, parts by weight: - 0.5
(2) Metalaxyl - 0.5
(3) Bentonite - 20
(4) Kaolin - 74
(5) Sodium ligninsulfonate - 5
The above components are mixed with an amount of water sufficient for granulation, then granulated and granules are obtained.

Example composition 7, parts by weight:
(1) Compound 3 - 0.25
(2) Metalaxyl - 0.25
(3) Calcium carbonate - 99.0
(4) Phosphate of lower alcohol - 0.5
The above components are mixed until smooth and get dust.

Example composition 8, parts by weight:
(1) Kaolin - 78
(2) Condensate of β-naphthalenesulfonate sodium and formaldehyde - 2
(3) Polyoxyethylene alkyl aryl sulfate - 5
(4) Hydrated Amorphous Silica - 15
A mixture of the above components, compound 1, Kocide Bordeaux (trademark), is mixed at a mass ratio of 0.8: 76.8: 22.4 to obtain a wettable powder.

Example composition 9, parts by weight:
(1) Kaolin - 78
(2) Condensate of β-naphthalenesulfonate sodium and formaldehyde - 2
(3) Polyoxyethylene alkyl aryl sulfate - 5
(4) Hydrated Amorphous Silica - 15
A mixture of the above components, compound 1 and Duitch Bordeaux A (trademark) is mixed at a mass ratio of 5: 67.2: 27.8 to obtain a wettable powder.

Example composition 10, parts by weight:
(1) Compound 1 - 0.25
(2) Dust DL Sanpun Bordeaux (trademark, manufactured by Dai-ichi Noyaku K.K. and Hokko Chemical Industry Co., Ltd.) - 0.25
(3) Sodium carbonate - 99.0
(4) Phosphate of lower alcohol - 0.5
The above components are mixed until smooth and get dust.

Example composition 11, parts by weight:
(1) Compound 1 - 0.5
(2) Dust DL Sanpun Bordeaux (trademark manufactured by Dai-ichi Noyaku K.K. and Hokko Chemical Industry Co., Ltd.) - 0.5
(3) Bentonite - 20
(4) Kaolin - 74
(5) Sodium ligninsulfonate - 5
The above components are mixed together with an amount of water sufficient for granulation, then granulated and granules are obtained.

An example of the composition 12, parts by weight:
(1) Compound 1 to 5
(2) Tris (ethylphosphonate) aluminum (fosetylaluminium) - 5
(3) Diatomaceous earth - 84
(4) Calcium Ligninsulfonate - 2
(5) Dialkyl sulfosuccinate - 4
The above components are mixed until homogeneous and get wettable powder.

POULENC) - 1,1
(3) Диспергатор и смачиватель Supragil MNS/90 (торговый знак) - 1,1
(4) Диспергатор и суспендирующий агент Vegum - 1,7
(5) Мочевина (действует как антифриз) - 11,1
(6) Противовспениватель SM5572F (торговый знак) - 0,1
(7) Дистиллированная вода - 73,8
Указанные выше компоненты (1)-(7) смешивают и подвергают мокрому измельчению до тех пор, пока средний размер частиц активного ингредиента не достигнет 2 мкм, и получают суспензию. К 90 ч. полученной суспензии добавляют 10 ч. усиливающего активность ингредиента, затем смешивают посредством встряхивания и получают концентрат водной суспензии.Example composition 13, parts by weight:
(1) Compound 1 (active ingredient) - 11.1
(2) SOPROPHOR FLK Dispersant (trademark, manufactured by

POULENC) - 1.1
(3) Dispersant and wetting agent Supragil MNS / 90 (trademark) - 1.1
(4) Dispersant and suspending agent Vegum - 1,7
(5) Urea (acts as antifreeze) - 11.1
(6) Anti-foaming agent SM5572F (trademark) - 0.1
(7) Distilled water - 73.8
The above components (1) to (7) are mixed and wet milled until the average particle size of the active ingredient reaches 2 μm, and a suspension is obtained. To 90 parts of the resulting suspension, 10 parts of the activity enhancing ingredient are added, then mixed by shaking to give an aqueous suspension concentrate.

POULENC) - 1,0
(3) Диспергатор и смачиватель Supragil MNS/90 (торговый знак) - 1,0
(4) Диспергатор и суспендирующий агент Vegum - 1,5
(5) Мочевина (действует как антифриз) - 10,0
(6) Противовспениватель SM5572F (торговый знак) - 0,1
(7) Дистиллированная вода - 66,4
(8) Усиливающий активность ингредиент - 10,0
Указанные выше компоненты (1)-(8) смешивают и подвергают мокрому измельчению до тех пор, пока средний размер частиц активного ингредиента не достигнет 2 мкм, и получают концентрат водной суспензии.An example composition 14, parts by weight:
(1) Compound 1 (active ingredient) - 10.0
(2) SOPROPHOR FLK Dispersant (trademark, manufactured by

POULENC) - 1.0
(3) Dispersant and Wetting Agent Supragil MNS / 90 (trademark) - 1.0
(4) Dispersant and suspending agent Vegum - 1,5
(5) Urea (acts as antifreeze) - 10.0
(6) Anti-foaming agent SM5572F (trademark) - 0.1
(7) Distilled water - 66.4
(8) Activity Enhancing Ingredient - 10.0
The above components (1) to (8) are mixed and wet milled until the average particle size of the active ingredient reaches 2 μm, and an aqueous suspension concentrate is obtained.

Reference example composition 15, parts by weight:
(1) Kaolin - 78
(2) Condensate of β-naphthalenesulfonate sodium and formaldehyde - 2
(3) Polyoxyethylene alkyl aryl sulfate - 5
(4) Hydrated Amorphous Silica - 15
The above components and the inorganic phosphorus compound are mixed in a 4: 1 weight ratio to obtain a 20% wettable powder based on the inorganic phosphorus compound.

Test Example 16
(1) Test methods and test results
Evaluation of the therapeutic effect in diseases of tomatoes
Preparation of an aqueous dispersion
Each of the distribution agents: 2-3, polyoxyethylene alkyl ether, 4-9, polyoxyethylene alkyl phenyl ether, 22, silicone surfactant, 67, mineral oil and Tween 20, is dispersed in water to give a concentration of 2000 ppm and then 4- chloro-2-cyano-1-dimethylsulfamoyl-5- (4-methylphenyl) imidazole (compound 1) to give a concentration of 400 ppm, resulting in an aqueous dispersion. As a control, in the same manner as the dispersion described above, an aqueous dispersion is prepared which does not contain an activity enhancing ingredient and contains compound 1 at a concentration of 400 ppm.

Biological Test Method and Results
Tomatoes (grade Ponderosa) are grown in plastic pots (diameter 7.5 cm). When the plant reaches the fourth leaf phase, it is infected by spraying with a suspension of zoosporangium of Phytophtora infestans fungi. After 4 hours, the plants are sprayed using a spray gun with the above-described aqueous dispersion at a rate of 10 ml / pot. A control aqueous dispersion containing compound 1 was also sprayed in a similar manner. The plant is kept in a chamber at a temperature of 22-24 ^o C for 3 days and determine the area of damage. The ratio of the lesion area of the sprayed sample to the lesion area of the sample with water control is calculated as the disease spread coefficient (%). The results are presented in table 35.

Test Example 17
Evaluation of the preventive effect in diseases of tomatoes
Preparation of an aqueous suspension
Each of the distribution agents: 4-5, polyoxyethylene alkyl phenyl ether, and 23, a silicone surfactant, is dispersed in water to obtain a concentration of 1000 ppm and then 4-chloro-2-cyano-1-dimethylsulfamoyl-5- (4 -methylphenyl) imidazole (compound 1) to obtain a concentration of 267 ppm, resulting in an aqueous dispersion. As a control sample, in the same manner as the dispersion described above, an aqueous dispersion is prepared which does not contain an activity enhancing ingredient and contains compound 1 at a concentration of 267 ppm.

Biological Test Method and Results
Tomatoes (grade Ponderosa) are grown in plastic pots (diameter 7.5 cm). Upon reaching the phase of the fourth leaf, the plant is sprayed using a sprayer of the above-described aqueous dispersion, which is brought to a predetermined concentration, at a rate of 300 liters / ha.

A control aqueous dispersion containing compound 1 was sprayed in the same manner. 24 hours after spraying, the plant is infected by spraying with a suspension of zoosporangia of Phytophtora infestans fungi. The plant is kept in a chamber at a temperature of 22-24 ^o C for 3 days and determine the area of damage. The ratio of the lesion area of the treated sample to the lesion area of the sample with water control is calculated as the incidence rate (%). The results are presented in table 37.

Test Example 18
Evaluation of the preventive effect of late blight of tomatoes
Tomatoes (grade Ponderosa) are grown in plastic pots (diameter 7.5 cm). Upon reaching the fourth leaf phase, the seedlings are sprayed with a sprayer of 10 ml of a composition containing an imidazole compound (compound 1 of this patent application or compound A-1b EP 337103) and one fungicide for phycomicets at the appropriate concentrations indicated in tables 35-40. After 24 hours, the plant is infected by spraying a suspension of zoosporangia of Phytophtora infestans fungi. The plant is kept in a chamber at a temperature of 22-24 ^o C for 3 days (table 35) or 4 days (other tables) and determine the area of damage, from which the incidence rate is calculated in accordance with the following formula. The results are shown in tables 35-40.

 The incidence rate (%) = (a / b) x 100, where a is the lesion area of the treated plant and b is the lesion area of the control (untreated plant).

 The theoretical incidence rate (%) can be calculated from the Colby formula below. In cases where the incidence rate of the test composition is lower than the theoretical incidence rate, the test composition may produce a synergistic effect. In these cases, the theoretical incidence rate (%) is presented in tables 35-42.

Theoretical incidence rate (%) = (X ¹ x Y ¹ ) / 100, where X ¹ represents the incidence rate (%) of a plant treated only with imidazole compound, and Y ¹ represents the incidence rate (%) of a plant treated only with fungicide for ficomycetes.

Test Example 19
Evaluation of the preventive effect of downy mildew of cucumbers
Cucumbers (grade Suyo) are grown in plastic pots (diameter 7.5 cm). When the plant reaches the second leaf phase, the seedlings are sprayed with a sprayer of 10 ml of the composition containing the imidazole compound (compound 1 of this patent application or compound A-1b EP337103) at the appropriate concentrations shown in tables 5 and 6. After 24 hours, the plant is infected by spraying with a suspension spores of powdery mildew fungi (Pseudoperonospora cubensis). The plant is kept in a chamber at a temperature of 22-24 ^o C for 5 days (table 42) or 6 days (table 41) and determine the area of damage, from which the incidence rate is calculated in accordance with the following formula. The results are shown in tables 41 and 42.

 The incidence rate (%) = (a / b) x 100, where a is the lesion area of the treated plant and b is the lesion area of the control (untreated plant).

The theoretical incidence rate (%) can be calculated from the Colby formula below. In cases where the incidence rate of the test composition is lower than the theoretical incidence rate, the test composition may produce a synergistic effect. In these cases, the theoretical disease spread rate (%) is presented in tables 41 and 42 in parentheses. Theoretical incidence rate (%) = (X ² x Y ² ) / 100, where X ² is the incidence rate (%) of a plant treated only with imidazole compound, and Y ² is the incidence rate (%) of a plant treated only with fungicide for ficomycetes.

Test Example 20
(1) Test methods and test results
Rating
therapeutic effect in diseases of tomatoes
Preparation of an aqueous dispersion
A silicone surfactant-based distribution agent 23, SILWET L-77 (see table 2), which enhances the action of the active ingredient, is dispersed in water to give a predetermined concentration, and then 4-chloro-2-cyano-1-dimethylsulfamoyl-5- (4 -methylphenyl) imidazole (compound 1) to obtain an aqueous dispersion.

 As a control sample, in the same manner as the dispersion described above, an aqueous dispersion is prepared which does not contain an activity enhancing ingredient and contains compound 1 at a predetermined concentration.

Biological Test Method and Results
Tomatoes (grade Ponderosa) are grown in plastic pots (diameter 7.5 cm). When the plant reaches the phase of the fourth sheet, it is sprayed with the above-described aqueous dispersion at the rate of 7.5 ml per 0.25 m ² . The control aqueous dispersion containing compound 1 is also sprayed in a similar manner using a spray gun. After 24 hours, the plants are infected by spraying a suspension of zoosporangia of Phytophtora infestans fungi. The plant is kept in a chamber at a temperature of 20 ^o C for 3 days and determine the area of damage to the leaves.

 The ratio of the lesion area of the treated sample to the lesion area of the sample with control is calculated as the disease spread coefficient (%). The results are presented in table 43.

Grade Scale:
0: no damage
1: damage less than 10%
2: damage 10% or more, but less than 25%
3: damage 25% or more, but less than 50%
4: damage 50% or more
The incidence rate (IR) = (indicator of damage to 1 sheet) + (indicator of damage to 1 sheet) + (indicator of damage to 2 sheets) + (indicator of damage to 3 sheets) + (indicator of damage to 4 sheets): 16x100.

Industrial applicability
Compositions for combating harmful bioorganisms in accordance with the present invention have a strong therapeutic and / or prophylactic effect on cultivated plants suffering from plant diseases caused by harmful bioorganisms and make it possible to combat harmful bioorganisms. In particular, compositions containing an activity enhancing ingredient exhibit an enhanced therapeutic effect, thereby reducing the amount of active ingredient used.

 Despite the fact that the invention is described in detail and with reference to characteristic variants of its embodiment, it will be obvious to specialists in this field of technology that various changes and modifications can be made without departing from the essence and scope of the invention.

Claims (11)

1. Composition for combating fungal diseases of cultivated plants containing (a) a compound of imidazole of the formula

where R represents a lower alkyl group or a lower alkoxy group;
n is 1,
as an active ingredient, and (b) one inorganic phosphorus compound selected from the group consisting of phosphoric acid, phosphorous acid and their salts, or one fungicide for phycomycetes which is selected from the group consisting of methyl- (E) -2- { 2- [6- (2-cyanophenoxy) pyrimidin-4-yloxy] phenyl} -3-methoxyacrylate, methyl- (E) -methoxyimino [α- (o-tolyloxy) -o-tolyl] acetate, 3-anilino-5 -methyl-5- (4-phenoxyphenyl) -1, 3-oxazolidine-2,4-dione, 1- (2-cyano-2-methoxyiminoacetyl) -3-ethylurea, tetrachloroisophthalonitrile, methyl N- (2-methoxyacetyl) -N- (2,6-xylyl) -DL-alaninate, (E, Z) -4- [3- (4-chlorophenyl) -3- (3,4-methoxyphenyl) acryloyl] -morpholine, inorganic copper-containing fungicide and aluminum tris (ethylphosphonate) as the active ingredient or (c) a distribution agent as an activity enhancing ingredient, which is silicone surfactant or mineral oil, where component (a) and the phosphorus compound are in a mass ratio of from 1: 50 to 5: 1, (a) and the fungicide are in a mass ratio of from 1: 2000 to 2000: 1, or ( a) and (c) are in the ratio mass / volume (kg / l) from 1: 5000 to 1: 0.25. 2. The composition of claim 1, wherein the composition comprises (a) an imidazole compound represented by formula (I)

where R represents a lower alkyl group or a lower alkoxy group;
n is 1,
as an active ingredient, and (b) one inorganic phosphorus compound selected from the group consisting of phosphoric acid, phosphorous acid and their salts, or one fungicide for phycomycetes which is selected from the group consisting of methyl- (E) -2- { 2- [6- (2-cyanophenoxy) pyrimidin-4-yloxy] phenyl} -3-methoxyacrylate, methyl- (E) -methoxyimino [α- (o-tolyloxy) -o-tolyl] acetate, 3-anilino-5 -methyl-5- (4-phenoxyphenyl) -1,3-oxazolidine-2,4-dione, 1- (2-cyano-2-methoxyiminoacetyl) -3-ethylurea, tetrachloroisophthalonitrile, methyl N- (2-methoxyacetyl) -N- (2,6-xylyl) -DL-alaninate, (E, Z) -4- [3- ( 4-chlorophenyl) -3- (3,4-methoxyphenyl) acryloyl] morpholine, inorganic copper-containing fungicide and aluminum tris (ethylphosphonate) as the active ingredient.  3. The composition of claim 2, wherein the active ingredient (b) is a single inorganic phosphorus compound that is selected from the group consisting of phosphoric acid, phosphorous acid, and salts thereof.  4. The composition according to p. 2, where the active ingredient (b) is one fungicide for ficomycetes, which is selected from the group consisting of methyl- (E) -2- {2- [6- (2-cyanophenoxy) pyrimidin-4-yloxy ] phenyl} -3-methoxyacrylate, methyl- (E) -methoxyimino [α- (o-tolyloxy) -o-tolyl] acetate, 3-anilino-5-methyl-5- (4-phenoxyphenyl) -1,3- oxazolidine-2,4-dione, 1- (2-cyano-2-methoxyiminoacetyl) -3-ethylurea, tetrachloroisophthalonitrile, methyl N- (2-methoxyacetyl) -N- (2,6-xylyl) -DL-alaninate, (E, Z) -4- [3- (4-chlorophenyl) -3- (3,4-methoxyphenyl) acryloyl] morpholine, inorganic copper-containing fungicide and tris (ethylphos Onat) aluminum.  5. The composition according to p. 4, where the imidazole compound and fungicide are in a mass ratio of from 1: 300 to 300: 1. 6. The composition according to p. 1, which contains (a) an imidazole compound represented by formula (I)

where R represents a lower alkyl group or a lower alkoxy group;
n is 1,
as an active ingredient, and (c) a distribution agent as an activity enhancing ingredient, which is a silicone surfactant or mineral oil. 7. A method of combating fungal diseases of cultivated plants, comprising applying to them a composition for combating fungal diseases of cultivated plants that contains (a) an imidazole compound represented by formula (I)

where R represents a lower alkyl group or a lower alkoxy group; and n is 1, as an active ingredient, and
(b) one inorganic phosphorus compound that is selected from the group consisting of phosphoric acid, phosphorous acid and their salts, or one fungicide for phycomycetes, which is selected from the group consisting of methyl- (E) -2- {2- [6- ( 2-cyanophenoxy) pyrimidin-4-yloxy] phenyl} -3-methoxyacrylate, methyl- (E) -methoxyimino [α- (o-tolyloxy) -o-tolyl] acetate, 3-anilino-5-methyl-5- ( 4-phenoxyphenyl) -1,3-oxazolidin-2,4-dione, 1- (2-cyano-2-methoxyiminoacetyl) -3-ethylurea, tetrachloroisophthalonitrile, methyl N- (2-methoxyacetyl) -N- (2, 6-xylyl) -DL-alaninate, (E, Z) -4- [3- (4-chlorophenyl) -3- (3,4-methoxyphenyl) acryl silt] -morpholine, an inorganic copper-containing fungicide and aluminum tris (ethylphosphonate), or (c) a distribution agent as an activity enhancing ingredient, which is a silicone surfactant or mineral oil, where component (a) and the phosphorus compound are in the mass ratio of 1: 5 to 1: 30, (a) and fungicide are in the mass ratio of 1: 2000 to 1000: 1, or (a) and (c) are in the ratio mass / volume (kg / l) of 1 : 5000 to 1: 0.25. 8. The method according to p. 7, where the composition contains (a) an imidazole compound represented by formula (I)

where R represents a lower alkyl group or a lower alkoxy group;
n is 1,
as an active ingredient, and (b) one inorganic phosphorus compound selected from the group consisting of phosphoric acid, phosphorous acid and their salts, or one fungicide for phycomycetes which is selected from the group consisting of methyl- (E) -2- { 2- [6- (2-cyanophenoxy) pyrimidin-4-yloxy] phenyl} -3-methoxyacrylate, methyl- (E) -methoxyimino [α- (o-tolyloxy) -o-tolyl] acetate, 3-anilino-5 -methyl-5- (4-phenoxyphenyl) -1,3-oxazolidine-2,4-dione, 1- (2-cyano-2-methoxyiminoacetyl) -3-ethylurea, tetrachloroisophthalonitrile, methyl N- (2-methoxyacetyl) -N- [2,6-xylyl) -DL-alaninate, (E, Z) -4- [3- ( 4-chlorophenyl) -3- (3,4-methoxyphenyl) acryloyl] morpholine, inorganic copper-containing fungicide and aluminum tris (ethylphosphonate) as the active ingredient. 9. The method of claim 1, wherein the composition comprises (a) an imidazole compound represented by formula (I)

where R represents a lower alkyl group or a lower alkoxy group;
n is 1,
as an active ingredient, and (c) a distribution agent as an activity enhancing ingredient, which is a silicone surfactant or mineral oil.  10. The method of claim 9, wherein the composition is in the form of an aqueous dispersion. 11. A method of enhancing the action of an agent that suppresses fungal diseases of cultivated plants containing, as an active ingredient, an imidazole compound represented by the formula (I)

where R represents a lower alkyl group or a lower alkoxy group;
n is 1,
which includes the use, along with the active ingredient, of a distribution agent (c) as an activity enhancing ingredient, which is a silicone surfactant or mineral oil, the imidazole compound and (c) being in a weight / volume ratio (kg / l) of 1: 5000 to 1: 0.25. Point priority
04/25/1997 PP 6,9,10,11;
July 11, 1997 under item 3;
08/19/1997 on pp. 1,2,4,5,7,8.

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