USH811H - Biocidal composition - Google Patents

Biocidal composition Download PDF

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Publication number
USH811H
USH811H US07/322,460 US32246089A USH811H US H811 H USH811 H US H811H US 32246089 A US32246089 A US 32246089A US H811 H USH811 H US H811H
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US
United States
Prior art keywords
compounds
compound
formula
halogen
group
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Abandoned
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US07/322,460
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English (en)
Inventor
Rikuo Nasu
Terumasa Komyoji
Toshio Nakajima
Kazumi Suzuki
Keiichiro Ito
Tekeshi Ohshima
Hideshi Yoshimura
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Ishihara Sangyo Kaisha Ltd
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Ishihara Sangyo Kaisha Ltd
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Priority claimed from JP63057920A external-priority patent/JP2606720B2/ja
Application filed by Ishihara Sangyo Kaisha Ltd filed Critical Ishihara Sangyo Kaisha Ltd
Assigned to ISHIHARA SANGYO KAISHA, LTD., reassignment ISHIHARA SANGYO KAISHA, LTD., ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: ITO, KEIICHIRO, KOMYOJI, TERUMASA, NAKAJIMA, TOSHIO, NASU, RIKUO, OHSHIMA, TEKESHI, SUZUKI, KAZUMI, YOSHIMURA, HIDESHI
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Publication of USH811H publication Critical patent/USH811H/en
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles

Definitions

  • This invention relates to a biocidal composition containing as active ingredients at least one imidazole compound of formula (I) shown below and at least one other specific compound.
  • imidazole compounds of formula (I) shown below are useful as a biocide for controlling harmful organisms, which were found by the inventors of the present invention as described in European Patent 298,196A.
  • the present invention relates to a biocidal composition for controlling harmful organisms containing, as active ingredients, at least one imidazole compound represented by formula (I): ##STR2## wherein R 1 represents a phenyl group, a halogen-substituted phenyl group, an alkyl group, or a halogen-substituted alkyl group; and Rz represents a halogen atom, and at least one compound selected from the group consisting of azole compounds, quinoxaline compounds, dithiocarbamate compounds, organic chlorine compounds, benzimidazole compounds, pyridinamine compounds, cyanoacetamide compounds, phenylamide compounds, sulfenic acid compounds, copper compounds, isoxazole compounds, organophosphorus compounds, N-halogenothioalkyl compounds, dicarboximide compounds, benzanilide compounds, benzamide compounds, piperazine compounds, pyridine compounds, pyrimidine compounds, piperidine compounds, morpho
  • the halogen atom includes fluorine, chlorine, bromine, and iodine atoms.
  • the alkyl group contains from 1 to 4 carbon atoms and mention may be made of, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group, etc.
  • a biocidal composition wherein the compound which is used in admixture with the imidazole compounds represented by formula (I) is at least one compound selected from the group consisting of azole compounds, quinoxaline compounds, dithiocarbamate compounds, organic chlorine compounds, benzimidazole compounds, pyridinamine compounds, cyanoacetamide compounds, phenylamide compounds, sulfenic acid compounds, copper compounds, isoxazole compounds, organophosphorus compounds, dicarboximide compounds, benzanilide compounds, and benzamide compounds.
  • a biocidal composition wherein the imidazole compound is represented by formula (I'): ##STR3## wherein R 1 ' represents a phenyl group or a halogen-substituted alkyl group; and R 2 ' represents a chlorine atom.
  • a biocidal composition whose main use is for a fungicide.
  • the imidazole compounds represented by formula (I) include compounds represented by formula (I-a) and/or compounds represented by formula (I-b): ##STR4##
  • JP-A as used herein means a "published unexamined patent application”.
  • the imidazole compounds represented by formula (I) can be prepared, for example, by the following reaction schemes. ##STR6## wherein Z represents a hydrogen atom, a chlorine atom, or a bromine atom; Y represents a chlorine atom, a fluorine atom, a bromine atom, or an iodine atom; Y' represents a chlorine atom, a bromine atom, or an iodine atom; and R 1 is as defined above. ##STR7## wherein Y, R 1 , and R 2 are as defined above.
  • Step 1 of process A and Process B are carried out, if desired, in the presence of a solvent and an acid acceptor.
  • the solvent which can be used includes aromatic hydrocarbons, e.g., benzene, toluene, xylene, chlorobenzene, etc.; cyclic or acyclic aliphatic hydrocarbons, e.g., chloroform, carbon tetrachloride, methylene chloride, dichloroethane, trichloroethane, n-hexane, cyclohexane, etc.; ethers, e.g., diethyl ether, dioxane, tetrahydrofuran, etc.; ketones, e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, etc.; nitriles, e.g., acetonitrile, propionitrile, etc.; and aprotic polar solvents, e.g., dimethylformamide, N-methylpyrrolidone, dimethyl sul
  • the acid acceptor which can be used includes inorganic bases such as alkali metal hydroxides, e.g., sodium hydroxide and potassium hydroxide, alkali metal or alkaline earth metal carbonates, e.g., anhydrous potassium carbonate and anhydrous calcium carbonate, alkali metal hydrides, e.g., sodium hydride, and alkali metals, e.g., metallic sodium; and organic basis, e.g., triethylamine.
  • inorganic bases such as alkali metal hydroxides, e.g., sodium hydroxide and potassium hydroxide, alkali metal or alkaline earth metal carbonates, e.g., anhydrous potassium carbonate and anhydrous calcium carbonate, alkali metal hydrides, e.g., sodium hydride, and alkali metals, e.g., metallic sodium; and organic basis, e.g., triethylamine.
  • Step 1 of Process A and Process B can be effected in the presence of an appropriate catalyst, such as a phase transfer catalyst (e.g., quaternary ammonium salt derivatives).
  • a phase transfer catalyst e.g., quaternary ammonium salt derivatives
  • the compound of formula (II) includes tautomers represented by the following formulae: ##STR9## wherein R 1 and R 2 are as defined above.
  • reaction mixture was poured into water and extracted with methylene chloride.
  • the extract was washed with water and dried over anhydrous sodium sulfate.
  • the solvent was removed by distillation, and the residue was purified by silica gel column chromatography using methylene chloride as a developing solvent to obtain 28.0 g of 2-cyano-1-dimethylsulfamoylimidazole having a melting point of from 74 to 76° C.
  • reaction mixture was poured into water and extracted with 500 ml of ethyl acetate.
  • the ethyl acetate layer was washed with water and dried over anhydrous sodium sulfate.
  • the ethyl acetate was removed by distillation, and the residue was purified by silica gel column chromatography using methylene chloride as a developing solvent and separated to give 4.8 g of 2-cyano-1-dimethylsulfamoyl-5-n-propylimidazole having a melting point of from 51 to 52° C.
  • the acetonitrile was removed by distillation from the reaction mixture. After pouring 100 ml of water into the residue, the resulting mixture was extracted with 50 ml of methylene chloride. The extract was washed with water and dried over anhydrous sodium sulfate. The methylene chloride was removed by distillation, and the residue was allowed to stand overnight at room temperature. The analysis of the residue revealed that one of the two isomers in the mixture decomposed and returned to the starting 4(5)-chloro-2-cyano-5(4)-n-propylimidazole.
  • reaction mixture was poured into water and extracted with chloroform. After washing with water, the extracted layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: methylene chloride) to give 1.28 g of 4(5)-chloro-2-cyano-5(4)-phenylimidazole having a melting point of from 149° to 151° C.
  • reaction mixture was poured into water and extracted with ethyl acetate. After washing with water, the extracted layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was then purified by silica gel column chromatography (developing solvent: methylene chloride) to give 0.5 g of 4(5)-chloro-2-cyano-1-dimethylsulfamoyl-5(4)phenylimidazole having a melting point of from 106° to 109° C.
  • the compound described above was found to be an isomeric mixture of 4-chloro-2-cyano-1-dimethylsulfamoyl-5-phenylimidazole and 5-chloro-2-cyano-1-dimethylsulfa- moyl-4-phenylimidazole in almost equal ratios.
  • biocidal compositions according to the present invention comprising the imidazole compound of formula (I) in combination with other specific compound, are particularly useful as agricultural fungicides. Specifically, they exhibit excellent effects of controlling diseases of crop plants such as rice blast caused by Pyricularia oryzae, rice sheath blight caused by Rhizoctonia solani, cucumber anthracnose caused by Colletotrichum lagenarium, cucumber powdery mildew caused by Sphaerotheca fuliginea, cucumber downy mildew caused by Pseudoperonospora cubensis, tomato late blight caused by Phytophthora infestans, tomato early blight caused by Alternaria solani, citrus melanose caused by Diaporthe citri, citrus common green mold caused by Penicillium digitatum, pear scab caused by Venturia nashicola, apple alternaria blotch caused by Alternaria mali, grape downy mildew caused by Plasmopara viticola,
  • biocidal compositions of the present invention exhibit excellent effects of controlling diseases such as potato or tomato late blight caused by Phytophthora infestans, cucumber downy mildew caused by Pseudoperonospora cubensis, grape downy mildew caused by Plasmopara viticola, tobacco blue mold caused by Peronospora tabacina; and various soil diseases caused by phycomycetes such as Plasmodiophora, Aphanomyces, Pythium, etc.
  • diseases such as potato or tomato late blight caused by Phytophthora infestans, cucumber downy mildew caused by Pseudoperonospora cubensis, grape downy mildew caused by Plasmopara viticola, tobacco blue mold caused by Peronospora tabacina
  • various soil diseases caused by phycomycetes such as Plasmodiophora, Aphanomyces, Pythium, etc.
  • biocidal compositions of the present invention have a prolonged residual effect so that they exhibit an excellent preventive effect, and also exhibit an excellent curative effect as well. It is therefore possible to control diseases by treatment after infection. In addition, since they possess a systemic activity, it is also possible to control diseases of the stem and leaf by soil treatment.
  • biocidal compositions of the present invention show an excellent controlling effect against agriculturally and horticulturally harmful insects such as planthoppers, diamondback moth (Plutella xylostella), green rice leafhopper (Nephotettix cincticeps), adzuki bean weevil (Callosobruchus chinensis), common cutworm (Spodoptera litura), green peach aphid (Myzus persicae), etc.; mites such as twospotted spider mite (Tetranychus urticae), carmine spider mite (Tetranychus cinnabarinus), citrus red mite (Panonychus citri), etc.; and nematodes such as southern root-knot nematode (Meloidogyne incognita), etc.
  • the compounds constituting the biocidal composition of the present invention can be formulated into a variety of forms, such as emulsifiable concentrates, dusts, wettable powders, aqueous solutions, granules, suspension concentrates, etc., together with various adjuvants, as in conventional agricultural preparations.
  • the imidazole compound of formula (I) and the other specific compound may be mixed and formulated, or each of the compounds may be separately formulated and then mixed together.
  • the preparation may be used as such or as diluted with an appropriate diluent, e.g., water, to a predetermined concentration.
  • adjuvants examples include carriers, emulsifying agents, suspending agents, dispersing agents, spreaders, penetrating agents, wetting agents, thickeners, stabilizers, etc. These adjuvants can be added appropriately according to necessity.
  • the carriers are classified into solid carriers and liquid carriers.
  • the solid carriers include animal and vegetable powders, e.g., starch, sugar, cellulose powders, cyclodextrin, activated charcoal, soybean powders, wheat powders, chaff powders, wood powders, fish powders, powdery milk, etc., and mineral powders, e.g., talc, kaolin, bentonite, bentonite-alkylamine complexes, calcium carbonate, calcium sulfate, sodium bicarbonate, zeolite, diatomaceous earth, white carbon, clay, alumina, silica, sulfur powders, etc.
  • animal and vegetable powders e.g., starch, sugar, cellulose powders, cyclodextrin, activated charcoal, soybean powders, wheat powders, chaff powders, wood powders, fish powders, powdery milk, etc.
  • mineral powders e.g., talc, kaolin, bentonite, bentonite
  • the liquid carriers include water, animal and vegetable oils, e.g., soybean oil, cotton seed oil, etc., alcohols, e.g., ethyl alcohol, ethylene glycol, etc., ketones, e.g., acetone, methyl ethyl ketone, etc., ethers, e.g., dioxane, tetrahydrofuran, etc., aliphatic hydrocarbons, e.g., kerosene, lamp oil, liquid paraffin, etc., aromatic hydrocarbons, e.g., xylene, trimethylbenzene, tetramethylbenzene, cyclohexane, solvent naphtha, etc., halogenated hydrocarbons, e.g., chloroform, chlorobenzene, etc., acid amides, e.g., dimethylformamide, etc., esters, e.g., ethyl acetate, fatty acid gly
  • a suitable mixing ratio of the imidazole compound of formula (I) and other specific compound usually ranges from 1:300 to 300:1, preferably from 1:100 to 100:1, and more preferably from 1:50 to 5:1, by weight.
  • concentration of the biocidal composition of the present invention is hard to specify as it varies depending on the crop to which the composition is applied, the method of application, the preparation form, the dose to be applied, and the like.
  • concentrations of the imidazole compound of formula (I) and the specific compound to be combined are from 1 to 1,000 ppm and from 1 to 5,000 ppm, respectively, in the case of foliar treatment, and those in the case of soil treatment are from 10 to 10,000 g/ha and from 10 to 50,000 g/ha, respectively.
  • biocidal compositions according to the present invention are hereinafter given for illustrative purposes only but not for limitation.
  • Tomato (cultivars: Ponderosa) was cultivated in a polyethylene pot having a diameter of 7.5 cm.
  • 10 ml of a solution obtained from each of test compounds adjusted to a predetermined concentration was sprayed over tomato using a spray gun.
  • a zoosporangium suspension of fungi of late blight (Phytophthora infestans) was inoculated by spraying.
  • Five days after the inoculation an area of lesion on the leaves was investigated, and an index of control was determined according to the following standard. The results obtained are shown in Tables 2-1 through 2-6.
  • the controlling effect was determined by visually observing a degree of disease of a test plant and expressed by the following 5 grades of the index of control.
  • Test Example 1 A test similar to Test Example 1 was carried out. The degree of disease has visually observed to determine the index of control according to the following standard for evaluation. The results obtained are shown in Tables 3-1 through 3-3.
  • Cucumber (cultivars: Suyo) was cultivated in a polyethylene pot having a diameter of 7.5 cm.
  • a spore suspension of fungi of downy mildew (Pseudoperonospora cubensis) was inoculated by spraying.
  • 10 ml of a solution of each of test compounds adjusted to a predetermined concentration was sprayed over cucumber using a spray gun.
  • an area of lesion on the first leaf was visually observed to determine the index of control according to the standard of Test Example 2. The results obtained are shown in Tables 5-1 through 5-3.
  • Cucumber (cultivars: Suyo) was cultivated in a polyethylene pot having a diameter of 7.5 cm.
  • 10 ml of a solution obtained from each of test compounds adjusted to a predetermined concentration has sprayed over cucumber using a spray gun.
  • a mycelial disc having a diameter of 5 mm of fungi of gray mold (Botrytis cinerea) was inoculated on the first leaf.
  • Three days after the inoculation a length of lesion was investigated, and an index of control was determined according to the standard of Test Example 2. The results shown in Table 6 were obtained.
  • Rice plant (cultivars: Chukyo Asahi) was cultivated in a polyethylene pot having a diameter of 7.5 cm.
  • 20 ml of a solution obtained from each of test compounds adjusted to a predetermined concentration was sprayed over rice plant using a spray gun.
  • rice straw in which fungi of sheath blight (Rhizoctonia solani) had been previously incubated was set between leaf sheath portions to inoculate.
  • a length of lesion was investigated, and an index of control was determined according to the standard of Test Example 2. The results shown in Table 7 were obtained.
  • Mycelial disc (agar punching) of preincubated Pythium aphanidermatum was transplanted on potato-dextrose agar medium (PDA medium) containing 100 ppm of streptomycin and a predetermined concentration of each of test compounds. After incubation at 22° C. for 48 hours, a diameter of mycellium was measured. Inhibition of hyphal growth (%) was determined by the following equation. The results shown in Table 8 were obtained. ##EQU1##
  • the above components are uniformly mixed to prepare a wettable powder.
  • a wettable powder can be prepared in the same manner as in Formulation Example 1, except for replacing Compound No. A-1b with 25 parts by weight of Compound No. A-12b and replacing Compound No. D-3 with 25 parts by weight of Compound No. I-1.
  • a wettable powder can be prepared in the same manner as in Formulation Example 1, except for replacing Compound No. D-3 with Compound No. K-1.
  • the above components are uniformly mixed to prepare a wettable powder.
  • a wettable powder can be prepared in the same manner as in Formulation Example 4, except for replacing Compound No. G-1 with Compound No. F-1.
  • a wettable powder can be prepared in the same manner as in Formulation Example 4, except for replacing Compound No. G-1 with Compound No. O1.
  • the above components are uniformly mixed to prepare a wettable powder.
  • a mixture consisting of the above components is mixed with Compound No. A-1b and Compound No. I-1 at a weight mixing ratio of 8:1:1 to prepare a wettable powder.
  • the above components are uniformly mixed to prepare a dust.
  • the above components are mixed and finely pulverized to prepare a suspension concentrate.
  • a suspension concentrate can be prepared in the same manner as in Formulation Example 14, except for replacing Compound No. D-3 with Compound No. E-2.

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
US07/322,460 1988-03-11 1989-03-13 Biocidal composition Abandoned USH811H (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP63057920A JP2606720B2 (ja) 1987-03-13 1988-03-11 イミダゾール系化合物及びそれらを含有する有害生物防除剤
JP63-57920 1988-03-11
JP22932788 1988-09-13
JP63-229327 1988-09-13

Publications (1)

Publication Number Publication Date
USH811H true USH811H (en) 1990-08-07

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ID=26399005

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US07/322,460 Abandoned USH811H (en) 1988-03-11 1989-03-13 Biocidal composition

Country Status (16)

Country Link
US (1) USH811H (enrdf_load_stackoverflow)
EP (1) EP0337103B1 (enrdf_load_stackoverflow)
KR (1) KR890013985A (enrdf_load_stackoverflow)
CN (1) CN1036879A (enrdf_load_stackoverflow)
AT (1) ATE85498T1 (enrdf_load_stackoverflow)
AU (1) AU609264B2 (enrdf_load_stackoverflow)
BR (1) BR8901097A (enrdf_load_stackoverflow)
DE (2) DE337103T1 (enrdf_load_stackoverflow)
ES (1) ES2014385T3 (enrdf_load_stackoverflow)
GR (2) GR900300071T1 (enrdf_load_stackoverflow)
HU (1) HU205833B (enrdf_load_stackoverflow)
IL (1) IL89475A0 (enrdf_load_stackoverflow)
MY (1) MY129863A (enrdf_load_stackoverflow)
NZ (1) NZ228284A (enrdf_load_stackoverflow)
PH (1) PH25549A (enrdf_load_stackoverflow)
PT (1) PT89972B (enrdf_load_stackoverflow)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5248675A (en) * 1990-03-15 1993-09-28 Tanabe Seiyaku Co., Ltd. Polysulfate of cyclodextrin derivative and process for preparing the same
US5250520A (en) * 1990-03-15 1993-10-05 Tanabe Seiyaku Co., Ltd. Polysulfate of cyclodextrin derivative and process for preparing the same
US5506216A (en) * 1993-04-23 1996-04-09 Boehringer Mannheim Gmbh Cyclodextrin-biocide complex
US5656281A (en) * 1989-12-14 1997-08-12 Rhone-Poulenc Agrochimie Water-dispersible granules of phosphite fungicidal products
US5891918A (en) * 1996-06-28 1999-04-06 Rohm And Haas Company Method for controlling resistant fungi

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9023082D0 (en) * 1990-10-24 1990-12-05 Schering Agrochemicals Ltd Fungicides
DE4122868A1 (de) * 1991-07-11 1993-01-14 Bayer Ag Mikrobizide wirkstoffkombinationen
DE4139950A1 (de) * 1991-12-04 1993-06-09 Bayer Ag, 5090 Leverkusen, De 2-cyanobenzimidazole, ein verfahren zu ihrer herstellung und ihre verwendung und neue vorprodukte
KR100368510B1 (ko) * 1994-09-08 2003-04-23 이시하라 산교 가부시끼가이샤 1-치환된-2-시아노이미다졸화합물의제조방법
FR2737085B1 (fr) * 1995-07-26 1997-08-22 Rhone Poulenc Agrochimie Associations insecticides d'un oxime carbamate avec un insecticide a groupe pyrazole ou phenylimidazole
JPH10109912A (ja) * 1996-10-04 1998-04-28 Akio Suganuma 抗菌組成物
CN1330238C (zh) 1997-04-25 2007-08-08 石原产业株式会社 防治有害生物的组合物和用该组合物防治有害生物的方法
WO2001014341A1 (fr) * 1999-08-19 2001-03-01 Ishihara Sangyo Kaisha, Ltd. Agents permettant de luter contre les maladies animales engendrees par des parasites
US6713500B2 (en) 1999-08-19 2004-03-30 Ishihara Sangyo Kaisha Ltd. Agent for controlling animal diseases caused by parasites
ATE372675T1 (de) * 2001-07-30 2007-09-15 Ishihara Sangyo Kaisha Zusammensetzung zur bekämpfung von pflanzenpathogenen bakterien und verfahren zur bekämpfung von pflanzenpathogenen bakterien
PL1769679T3 (pl) 2004-07-16 2011-06-30 Ishihara Sangyo Kaisha Bakteriobójcza kompozycja do stosowania w rolnictwie i ogrodnictwie oraz sposób zwalczania chorób roślin
CN101312649B (zh) * 2005-11-22 2012-03-28 石原产业株式会社 农业园艺用杀菌剂组合物以及植物病害的防除方法
JP5584532B2 (ja) * 2009-07-06 2014-09-03 石原産業株式会社 農園芸用殺菌剤組成物及び植物病害の防除方法
WO2019022857A1 (en) * 2017-07-28 2019-01-31 Dow Global Technologies Llc USE OF A NON-OXIDIZING BIOCIDE FOR THE SELECTIVE RECOVERY OF PRECIOUS METALS IN A FOAM FLOTATION PROCESS

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0298196A1 (en) 1987-03-13 1989-01-11 Ishihara Sangyo Kaisha, Ltd. Imidazole compounds and biocidal compositions comprising the same

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0298196A1 (en) 1987-03-13 1989-01-11 Ishihara Sangyo Kaisha, Ltd. Imidazole compounds and biocidal compositions comprising the same

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5656281A (en) * 1989-12-14 1997-08-12 Rhone-Poulenc Agrochimie Water-dispersible granules of phosphite fungicidal products
US5248675A (en) * 1990-03-15 1993-09-28 Tanabe Seiyaku Co., Ltd. Polysulfate of cyclodextrin derivative and process for preparing the same
US5250520A (en) * 1990-03-15 1993-10-05 Tanabe Seiyaku Co., Ltd. Polysulfate of cyclodextrin derivative and process for preparing the same
US5506216A (en) * 1993-04-23 1996-04-09 Boehringer Mannheim Gmbh Cyclodextrin-biocide complex
US5891918A (en) * 1996-06-28 1999-04-06 Rohm And Haas Company Method for controlling resistant fungi

Also Published As

Publication number Publication date
MY129863A (en) 2007-05-31
ATE85498T1 (de) 1993-02-15
PT89972A (pt) 1989-10-04
KR890013985A (ko) 1989-10-21
GR900300071T1 (en) 1991-07-31
EP0337103A3 (en) 1990-01-17
HUT54867A (en) 1991-04-29
IL89475A0 (en) 1989-09-10
ES2014385T3 (es) 1994-08-01
EP0337103B1 (en) 1993-02-10
BR8901097A (pt) 1989-10-31
CN1036879A (zh) 1989-11-08
AU3109389A (en) 1989-09-14
DE68904792T2 (de) 1993-07-01
DE337103T1 (de) 1990-06-13
AU609264B2 (en) 1991-04-26
HU205833B (en) 1992-07-28
ES2014385A4 (es) 1990-07-16
GR3007247T3 (enrdf_load_stackoverflow) 1993-07-30
NZ228284A (en) 1991-01-29
PH25549A (en) 1991-08-08
PT89972B (pt) 1994-01-31
EP0337103A2 (en) 1989-10-18
DE68904792D1 (de) 1993-03-25

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