WO2009119842A1 - 農園芸用殺菌剤組成物及び植物病害の防除方法 - Google Patents
農園芸用殺菌剤組成物及び植物病害の防除方法 Download PDFInfo
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- WO2009119842A1 WO2009119842A1 PCT/JP2009/056380 JP2009056380W WO2009119842A1 WO 2009119842 A1 WO2009119842 A1 WO 2009119842A1 JP 2009056380 W JP2009056380 W JP 2009056380W WO 2009119842 A1 WO2009119842 A1 WO 2009119842A1
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- polyoxin
- fungicide composition
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- VEMKTZHHVJILDY-FIWHBWSRSA-N resmethrin Chemical compound CC1(C)[C@H](C=C(C)C)C1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-FIWHBWSRSA-N 0.000 description 1
- 229940080817 rotenone Drugs 0.000 description 1
- JUVIOZPCNVVQFO-UHFFFAOYSA-N rotenone Natural products O1C2=C3CC(C(C)=C)OC3=CC=C2C(=O)C2C1COC1=C2C=C(OC)C(OC)=C1 JUVIOZPCNVVQFO-UHFFFAOYSA-N 0.000 description 1
- JJSYXNQGLHBRRK-SFEDZAPPSA-N ryanodine Chemical compound O([C@@H]1[C@]([C@@]2([C@]3(O)[C@]45O[C@@]2(O)C[C@]([C@]4(CC[C@H](C)[C@H]5O)O)(C)[C@@]31O)C)(O)C(C)C)C(=O)C1=CC=CN1 JJSYXNQGLHBRRK-SFEDZAPPSA-N 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- HPYNBECUCCGGPA-UHFFFAOYSA-N silafluofen Chemical compound C1=CC(OCC)=CC=C1[Si](C)(C)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 HPYNBECUCCGGPA-UHFFFAOYSA-N 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- MXMXHPPIGKYTAR-UHFFFAOYSA-N silthiofam Chemical compound CC=1SC([Si](C)(C)C)=C(C(=O)NCC=C)C=1C MXMXHPPIGKYTAR-UHFFFAOYSA-N 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 229940014213 spinosad Drugs 0.000 description 1
- GOLXNESZZPUPJE-UHFFFAOYSA-N spiromesifen Chemical compound CC1=CC(C)=CC(C)=C1C(C(O1)=O)=C(OC(=O)CC(C)(C)C)C11CCCC1 GOLXNESZZPUPJE-UHFFFAOYSA-N 0.000 description 1
- CLSVJBIHYWPGQY-GGYDESQDSA-N spirotetramat Chemical compound CCOC(=O)OC1=C(C=2C(=CC=C(C)C=2)C)C(=O)N[C@@]11CC[C@H](OC)CC1 CLSVJBIHYWPGQY-GGYDESQDSA-N 0.000 description 1
- PUYXTUJWRLOUCW-UHFFFAOYSA-N spiroxamine Chemical compound O1C(CN(CC)CCC)COC11CCC(C(C)(C)C)CC1 PUYXTUJWRLOUCW-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 150000003450 sulfenic acids Chemical class 0.000 description 1
- CCEKAJIANROZEO-UHFFFAOYSA-N sulfluramid Chemical compound CCNS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F CCEKAJIANROZEO-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 239000005936 tau-Fluvalinate Chemical class 0.000 description 1
- INISTDXBRIBGOC-XMMISQBUSA-N tau-fluvalinate Chemical class N([C@H](C(C)C)C(=O)OC(C#N)C=1C=C(OC=2C=CC=CC=2)C=CC=1)C1=CC=C(C(F)(F)F)C=C1Cl INISTDXBRIBGOC-XMMISQBUSA-N 0.000 description 1
- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 description 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- WOSNCVAPUOFXEH-UHFFFAOYSA-N thifluzamide Chemical compound S1C(C)=NC(C(F)(F)F)=C1C(=O)NC1=C(Br)C=C(OC(F)(F)F)C=C1Br WOSNCVAPUOFXEH-UHFFFAOYSA-N 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- OPASCBHCTNRLRM-UHFFFAOYSA-N thiometon Chemical compound CCSCCSP(=S)(OC)OC OPASCBHCTNRLRM-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- QSOHVSNIQHGFJU-UHFFFAOYSA-L thiosultap disodium Chemical compound [Na+].[Na+].[O-]S(=O)(=O)SCC(N(C)C)CSS([O-])(=O)=O QSOHVSNIQHGFJU-UHFFFAOYSA-L 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- VJQYLJSMBWXGDV-UHFFFAOYSA-N tiadinil Chemical compound N1=NSC(C(=O)NC=2C=C(Cl)C(C)=CC=2)=C1C VJQYLJSMBWXGDV-UHFFFAOYSA-N 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical group COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- WPALTCMYPARVNV-UHFFFAOYSA-N tolfenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(OC=3C=CC(C)=CC=3)=CC=2)=C1Cl WPALTCMYPARVNV-UHFFFAOYSA-N 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical class CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- DBXFMOWZRXXBRN-LWKPJOBUSA-N valifenalate Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)NC(CC(=O)OC)C1=CC=C(Cl)C=C1 DBXFMOWZRXXBRN-LWKPJOBUSA-N 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000010698 whale oil Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
Classifications
-
- 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
- the present invention relates to a fungicide composition for agricultural and horticultural use having a plant disease control effect, particularly an effect of preventing and / or treating plant disease, and a plant disease control method using the composition.
- Patent Document 1 describes that an imidazole compound, which is an active ingredient of the agricultural and horticultural fungicide composition of the present invention, is useful as a pest control agent, and can be mixed with other fungicides as necessary. There is a description that they can be used together. Polyoxins are antibiotics described in Patent Document 2. However, these publications do not describe combinations of active ingredient compounds in the agricultural and horticultural fungicide composition of the present invention.
- Each of the imidazole compounds represented by the formula (I) described below may have a plant disease control effect that is not sufficient for a specific plant disease or has a relatively short residual effect. Then, it may show only an insufficient control effect practically against plant diseases.
- the present inventors have used polyoxins in combination with imidazole compounds represented by the following formula (I) to use each drug alone.
- the present invention was completed by obtaining the knowledge that an even more excellent plant disease control effect could be obtained that could not be expected.
- the present invention relates to an agricultural and horticultural fungicide composition characterized by containing
- the present invention also relates to a method for controlling plant diseases, which comprises applying the agricultural and horticultural fungicide composition to plants.
- the C 1-6 alkyl group or the alkyl part of the C 1-6 alkoxy group defined by R is alkyl having 1 to 6 carbon atoms such as methyl, ethyl, Examples include propyl, butyl, pentyl, hexyl, which may be linear or branched. When n is 2 or more, R may be the same or different.
- Examples of the imidazole compound represented by the formula (I) include the following compounds. 4-Chloro-2-cyano-1-dimethylsulfamoyl-5- (4-methylphenyl) imidazole (Compound No. 1) 4-Chloro-2-cyano-1-dimethylsulfamoyl-5- (4-methoxyphenyl) imidazole (Compound No. 2) 4-Chloro-2-cyano-1-dimethylsulfamoyl-5- (4-ethylphenyl) imidazole (Compound No. 3) 4-Chloro-2-cyano-1-dimethylsulfamoyl-5- (3-methyl-4-methoxyphenyl) imidazole (Compound No.
- the imidazole compound represented by the formula (I) can be produced by a method described in European Patent Application Publication No. 298196 and European Patent Application Publication No. 705823.
- Compound No. 1 is a compound known as the general name Cyazofamid.
- the polyoxin used as the active ingredient (b) in the present invention is a substance described on pages 795-797 of The Pesticide Manual (13th edition; BRITISH CROP PROTECTION COUNCIL 2003). Polyoxin is not a single compound but a complex of a series of compounds having chemical structures similar to each other, and those containing polyoxin B as the main component and those containing polyoxin D as the main component are used as bactericides. . Any of them can be used in the present invention.
- the fungicide composition for agricultural and horticultural use comprising (a) at least one imidazole compound represented by the formula (I) and (b) polyoxin as active ingredients, which infects harmful diseases.
- Cultivated crops that may or may be, such as cucumbers, tomatoes, eggplants and other sugar beets; rice, wheat and other cereals; legumes, apples, pears, grapes, citrus and other fruit trees; potatoes, etc.
- the agricultural and horticultural fungicide composition of the present invention has a long residual effect, excellent osmotic transferability, and has a preventive effect and / or a therapeutic effect, and is particularly excellent in a preventive effect.
- the agricultural and horticultural fungicide composition of the present invention specifically includes rice blast disease; rice sheath blight; rice seedling blight; cucumber anthracnose; cucumber, melon, cabbage, cabbage, onion, pumpkin, grape Downy mildew; wheat, barley, cucumber powdery mildew; potato, pepper, pepper, watermelon, pumpkin, tobacco, tomato plague; wheat septoria disease; tomato ringspot; citrus sunspot; citrus green mold; Pear scab; apple spotted leaf blight; onion white plague; brown rot of watermelon; various gray molds, mycorrhizal disease, rust, spotted bacterial diseases; Fusarium, Psium, Rhizoctonia, Verti Excellent control effect against various soil diseases caused by plant pathogens such as silicium.
- the active ingredient constituting the agricultural and horticultural fungicide composition according to the present invention is blended with various adjuvants as in the case of conventional agricultural chemical preparations, and emulsions, powders, wettable powders, liquids, granules, suspension preparations, etc. Can be formulated into various forms.
- the imidazole compound represented by the formula (I) and another specific compound may be mixed and formulated together, or may be separately formulated and mixed. In actual use of these preparations, they can be used as they are or after diluting to a predetermined concentration with a diluent such as water.
- auxiliary agent examples include carriers, emulsifiers, suspending agents, thickeners, stabilizers, dispersants, spreading agents, wetting agents, penetrating agents, antifreezing agents, antifoaming agents, and the like. What is necessary is just to add suitably.
- the carrier examples include a solid carrier and a liquid carrier. Examples of the solid carrier include starch, sugar, cellulose powder, cyclodextrin, activated carbon, soybean powder, wheat flour, rice bran powder, wood powder, fish powder, and milk powder.
- Kerosene light Aliphatic hydrocarbons such as liquid paraffin; aromatic hydrocarbons such as toluene, xylene, trimethylbenzene, tetramethylbenzene, cyclohexane and solvent naphtha; halogenated hydrocarbons such as chloroform and chlor
- the spreading agent examples include sodium alkyl sulfate, sodium alkylbenzene sulfonate, sodium lignin sulfonate, polyoxyethylene glycol alkyl ether, polyoxyethylene lauryl ether, polyoxyethylene alkylaryl ether, polyoxyethylene sorbitan fatty acid ester, and the like. .
- fungicide for example, Anilinopyrimidinamine compounds such as mepanipyrim, pyrimethanil, cyprodinil; Pyridinamine compounds such as fluazinam; Triadimefon, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, microbutanil, cyproconazole cyproconazole), tebuconazole, hexaconazole, furconazole-cis, prochloraz, metconazole, epoxiconazole, tetraconazole, o Oxpoconazole fumarate, sipconazole, prothioconazole, triadimenol, flutriafol, difenoconazole , Fluquinconazole, fen
- pesticides as an insecticide, acaricide, or nematicide, that is, an active ingredient compound of a pesticide (generic name; including some pending applications), for example, profenofos, dichlorvos ( dichlorvos, fenamiphos, fenitrothion, EPN, diazinon, chlorpyrifos-methyl, acephate, prothiofos, fothhiazate, phosphocarb, phosphocarb, cadusafos), disulfoton, chlorpyrifos, demeton-S-methyl, dimethoate, metamidophos, imicyafos, isoxathion, isoxathion, isofenphos , Etion, etrim Etrimfos, quinalphos, dimethylvinphos, sulprofos, thiometon, bamidothion, pyraclofos, pyrida pesticide (generic name; including
- Bacillus thuringienses aizawai, Bacillus thuringienses kurstaki, Bacillus thuringienses israelensis, Bacillus thuringienses japonensis, crystal protein toxins produced by Bacillus thuringienses tenebrionis or Bacillus thuringienses; Microbial pesticides such as: avermectin, milbemectin, milbemycin, spinosad, emamectin benzoate, ivermectin, lepimectin, spinetoram, spinetoram, It can also be used in combination with antibiotics such as abamectin and emamectin; natural products such as azadirachtin and rotenone; and repellents such as deet.
- Microbial pesticides such as: avermectin, milbemectin, milbemycin, spinosad, emame
- an appropriate mixing weight ratio of at least one imidazole compound represented by formula (I) and polyoxin exhibits a synergistic effect when both are combined. It is desirable that the blending ratio be an effective amount (synergistically effective amount) of each of the above, generally 1: 10000 to 10000: 1, desirably 1: 1000 to 1000: 1, more desirably 1: 100 to 100. : 1.
- the plant disease control method of applying the agricultural and horticultural fungicide composition of the present invention to a plant is also included in the present invention.
- concentration of the active ingredient used in the agricultural and horticultural fungicide composition of the present invention varies depending on the conditions such as the target crop, method of use, formulation form, application rate, application time, type of harmful fungus, etc.
- the concentration of the active ingredient is usually 0.01 to 1,000 ppm, preferably 0.3 to 500 ppm of the imidazole compound represented by the formula (I), and polyoxin is contained. It is 0.1 to 10,000 ppm, desirably 0.5 to 5000 ppm.
- the agricultural and horticultural fungicide composition of the present invention has a stable and high control effect on cultivated crops infected with plant diseases, and plant diseases can be controlled using this composition.
- An agricultural and horticultural fungicide composition comprising (a) at least one imidazole compound represented by formula (I) and (b) polyoxin as active ingredients.
- Disinfectant composition (4) Agricultural and horticultural use according to the above (1), wherein the weight ratio of (a) at least one imidazole compound represented by formula (I) to (b) polyoxin is 1: 1000 to 1000: 1. Disinfectant composition. (5) The agricultural and horticultural fungicide composition according to (1), wherein the imidazole compound represented by the formula (I) is cyazofamide.
- Test example 1 Pythium spinosum hyphal elongation inhibitory effect test
- the strain used for the test was pre-cultured in PSA plate medium at 20 ° C for 2 days, and the grown hyphae were punched out with a cork borer with a diameter of 4 mm, and active compound was placed on a PDA plate medium prepared by diluting to contain a predetermined concentration.
- Table 1 The results are shown in Table 1.
- the theoretical value of the inhibition rate was calculated according to Colby's formula and described in parentheses in Table 1.
- the agricultural and horticultural fungicide composition of the present invention has a synergistic effect on the control of plant diseases.
- Test example 2 Pythium graminicola hyphal elongation inhibitory effect test In the same manner as in Test Example 1, hyphal elongation was measured, the inhibition rate was examined, and the results are shown in Table 2. The average mycelial elongation of the untreated group was 46.5 mm.
- Formulation Example 1 (I) 2 parts by weight of cyazofamide, (b) 10 parts by weight of a polyoxin complex composed mainly of polyoxin B, (5) 5 parts by weight of a sodium naphthalene sulfonate formalin condensate, (E) Clay 78 parts by weight The above components are mixed to obtain a wettable powder.
- Formulation Example 2 (A) 0.5 parts by weight of cyazofamide, (b) 2.5 parts by weight of a polyoxin complex containing polyoxin B as a main component, (c) 20 parts by weight of calcium carbonate, (d) 77 parts by weight of clay To obtain a powder.
- the agricultural and horticultural fungicide composition of the present invention has a stable and high control effect on cultivated crops infected with plant diseases, and plant diseases can be controlled using this composition.
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- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
・4-クロロ-2-シアノ-1-ジメチルスルファモイル-5-(4-メチルフェニル)イミダゾール(化合物No.1)
・4-クロロ-2-シアノ-1-ジメチルスルファモイル-5-(4-メトキシフェニル)イミダゾール(化合物No.2)
・4-クロロ-2-シアノ-1-ジメチルスルファモイル-5-(4-エチルフェニル)イミダゾール(化合物No.3)
・4-クロロ-2-シアノ-1-ジメチルスルファモイル-5-(3-メチル-4-メトキシフェニル)イミダゾール(化合物No.4)
なお、前記式(I)で表されるイミダゾール系化合物は、欧州特許出願公開第298196号明細書及び欧州特許出願公開第705823号明細書などに記載された方法によって製造することができる。また、化合物No.1は、一般名シアゾファミド(Cyazofamid)として知られた化合物である。
メパニピリム(mepanipyrim)、ピリメサニル(pyrimethanil)、シプロジニル(cyprodinil)のようなアニリノピリミジナミン系化合物;
フルアジナム(fluazinam)のようなピリジナミン系化合物;
トリアジメホン(triadimefon)、ビテルタノール(bitertanol)、トリフルミゾール(triflumizole)、エタコナゾール(etaconazole)、プロピコナゾール(propiconazole)、ペンコナゾール(penconazole)、フルシラゾール(flusilazole)、マイクロブタニル(myclobutanil)、シプロコナゾール(cyproconazole)、テブコナゾール(tebuconazole)、ヘキサコナゾール(hexaconazole)、ファーコナゾールシス(furconazole‐cis)、プロクロラズ(prochloraz)、メトコナゾール(metconazole)、エポキシコナゾール(epoxiconazole)、テトラコナゾール(tetraconazole)、オキスポコナゾールフマル酸塩(oxpoconazole fumarate)、シプコナゾール(sipconazole)、プロチオコナゾール(prothioconazole)、トリアジメノール(triadimenol)、フルトリアホール(flutriafol)、ジフェノコナゾール(difenoconazole)、フルキンコナゾール(fluquinconazole)、フェンブコナゾール(fenbuconazole)、ブロムコナゾール(bromuconazole)、ジニコナゾール(diniconazole)、トリシクラゾール(tricyclazole)、プロベナゾール(probenazole)、シメコナゾール(simeconazole)、ペフラゾエート(pefurazoate)、イプコナゾール(ipconazole)、イミベンコナゾール(imibenconazole)のようなアゾール系化合物;
キノメチオネート(quinomethionate)のようなキノキサリン系化合物;
マンネブ(maneb)、ジネブ(zineb)、マンゼブ(mancozeb)、ポリカーバメート(polycarbamate)、メチラム(metiram)、プロピネブ(propineb)、チラム(thiram)のようなジチオカーバメート系化合物;
フサライド(fthalide)、クロロタロニル(chlorothalonil)、キントゼン(quintozene)のような有機塩素系化合物;
ベノミル(benomyl)、チオファネートメチル(thiophanate‐methyl)、カーベンダジム(carbendazim)、チアベンダゾール(thiabendazole)、フベリアゾール(fuberiazole)のようなイミダゾール系化合物;
シモキサニル(cymoxanil)のようなシアノアセトアミド系化合物;
メタラキシル(metalaxyl)、メタラキシル-M(metalaxyl-M)、メフェノキサム(mefenoxam)、オキサジキシル(oxadixyl)、オフレース(ofurace)、ベナラキシル(benalaxyl)、ベナラキシル-M(benalaxyl-M、別名キララキシル(kiralaxyl、chiralaxyl))、フララキシル(furalaxyl)、シプロフラム(cyprofuram)のようなフェニルアミド系化合物;
ジクロフルアニド(dichlofluanid)のようなスルフェン酸系化合物;
水酸化第二銅(cupric hydroxide)、有機銅(oxine Copper)のような銅系化合物;
ヒメキサゾール(hymexazol)のようなイソキサゾール系化合物;
ホセチルアルミニウム(fosetyl‐Al)、トルコホスメチル(tolcofos‐Methyl)、S-ベンジル O,O-ジイソプロピルホスホロチオエート、O-エチル S,S-ジフェニルホスホロジチオエート、アルミニウムエチルハイドロゲンホスホネート、エジフェンホス(edifenphos)、イプロベンホス(iprobenfos)のような有機リン系化合物;
キャプタン(captan)、キャプタホル(captafol)、フォルペット(folpet)のようなN-ハロゲノチオアルキル系化合物;
プロシミドン(procymidone)、イプロジオン(iprodione)、ビンクロゾリン(vinclozolin)のようなジカルボキシイミド系化合物;
フルトラニル(flutolanil)、メプロニル(mepronil)、ゾキサミド(zoxamide)、チアジニル(tiadinil)のようなベンズアニリド系化合物;
カルボキシン(carboxin)、オキシカルボキシン(oxycarboxin)、チフルザミド(thifluzamide)、ペンチオピラド(penthiopyrad)、ボスカリド(boscalid)、ビキサフェン(bixafen)、フルオピラム(fluopyram)、イソチアニル(isotianil)のようなアニリド系化合物;
トリホリン(triforine)のようなピペラジン系化合物;
ピリフェノックス(pyrifenox)のようなピリジン系化合物;
フェナリモル(fenarimol)、フルトリアフォル(flutriafol)のようなカルビノール系化合物;
フェンプロピディン(fenpropidin)のようなピペリジン系化合物;
フェンプロピモルフ(fenpropimorph)、スピロキサミン(spiroxamine)、トリデモルフ(Tridemorph)のようなモルフォリン系化合物;
フェンチンヒドロキシド(fentin hydroxide)、フェンチンアセテート(fentin acetate)のような有機スズ系化合物;
ペンシキュロン(pencycuron)のような尿素系化合物;
ジメトモルフ(dimethomorph)、フルモルフ(flumorph)のようなシンナミック酸系化合物;
ジエトフェンカルブ(diethofencarb)のようなフェニルカーバメート系化合物;
フルジオキソニル(fludioxonil)、フェンピクロニル(fenpiclonil)のようなシアノピロール系化合物;
アゾキシストロビン(azoxystrobin)、クレソキシムメチル(kresoxim‐methyl)、メトミノフェン(metominofen)、トリフロキシストロビン(trifloxystrobin)、ピコキシストロビン(picoxystrobin)、オリザストロビン(oryzastrobin)、ジモキシストロビン(dimoxystrobin)、ピラクロストロビン(pyraclostrobin)、フルオキサストロビン(fluoxastrobin)のようなストロビルリン系化合物;
ファモキサドン(famoxadone)のようなオキサゾリジノン系化合物;
エタボキサム(ethaboxam)のようなチアゾールカルボキサミド系化合物;
シルチオファム(silthiopham)のようなシリルアミド系化合物;
イプロバリカルブ(iprovalicarb)、ベンチアバリカルブ-イソプロピル(benthiavalicarb-isopropyl)、バリフェナール(valiphenal)のようなアミノアシッドアミドカーバメート系化合物;
フェナミドン(fenamidone)のようなイミダゾリジン系化合物;
フェンヘキサミド(fenhexamid)のようなハイドロキシアニリド系化合物;
フルスルファミド(flusulfamid)のようなベンゼンスルホンアミド系化合物;
シフルフェナミド(cyflufenamid)のようなオキシムエーテル系化合物;
フェノキサニル(fenoxanil)のようなフェノキシアミド系化合物;
アトラキノン系化合物;
クロトン酸系化合物;
バリダマイシン(validamycin)、カスガマイシン(kasugamycin)のような抗生物質;
イミノクタジン(iminoctadine)のようなグアニジン系化合物;
その他の化合物として、ピリベンカルブ(pyribencarb)、イソプロチオラン(isoprothiolane)、ピロキロン(pyroquilon)、ジクロメジン(diclomezine)、キノキシフェン(quinoxyfen)、プロパモカルブ塩酸塩(propamocarb hydrochloride)クロルピクリン(chloropicrin)、ダゾメット(dazomet)、メタムナトリウム塩(metam‐sodium)、ニコビフェン(nicobifen)、メトラフェノン(metrafenone)、UBF-307、ジクロシメット(diclocymet)、プロキンアジド(proquinazid)、アミスルブロム(amisulbrom;別名アミブロドール(amibromdole))、Syngenta 446510(mandipropamid、dipromandamid)、フルオピコリド(fluopicolide)、カルプロパミド(carpropamid)、BCF051、BCM061、BCM062、AF-0201などが挙げられる。
カルバリル(carbaryl)、プロポキスル(propoxur)、アルジカルブ(aldicarb)、カルボフラン(carbofuran)、チオジカルブ(thiodicarb)、メソミル(methomyl)、オキサミル(oxamyl)、エチオフェンカルブ(ethiofencarb)、ピリミカルブ(pirimicarb)、フェノブカルブ(fenobucarb)、カルボスルファン(carbosulfan)、ベンフラカルブ(benfuracarb)、ベンダイオカルブ(bendiocarb)、フラチオカルブ(furathiocab)、イソプロカルブ(isoprocarb)、メトルカルブ(metolcarb)、キシリルカルブ(xylylcarb)、XMC、フェノチオカルブ(fenothiocarb)のようなカーバメート系化合物;
カルタップ(cartap)、チオシクラム(thiocyclam)、ベンスルタップ(bensultap)、チオスルタップナトリウム(thiosultap-sodium)のようなネライストキシン誘導体;
ジコホル(dicofol)、テトラジホン(tetradifon)、エンドスルファン(endosulfan)、ジエノクロル(dienochlor)、ディルドリン(dieldrin)のような有機塩素系化合物;
酸化フェンブタスズ(fenbutatin Oxide)、シヘキサチン(cyhexatin)のような有機金属系化合物;
フェンバレレート(fenvalerate)、ペルメトリン(permethrin)、シペルメトリン(cypermethrin)、デルタメトリン(deltamethrin)、シハロトリン(cyhalothrin)、テフルトリン(tefluthrin)、エトフェンプロックス(ethofenprox)、フルフェンプロックス(flufenprox)、フェンプロパトリン(fenpropathrin)、ビフェントリン(bifenthrin)、イミデート(imidate)、シフルトリン(cyfluthrin)、フルシトリネート(flucythrinate)、フルバリネート(fluvalinate)、シクロプロトリン(cycloprothrin)、ラムダシハロトリン(lambda-cyhalothrin)、ピレスリン(pyrethrins)、エスフェンバレレート(esfenvalerate)、テトラメスリン(tetramethrin)、レスメスリン(resmethrin)、プロトリフェンブト(protrifenbute)、ゼータシペルメトリン(zeta-cypermethrin)、アクリナトリン(acrinathrin)、アルファシペルメトリン(alpha-cypermethrin)、アレスリン(allethrin)、ガンマシハロトリン(gamma-cyhalothrin)、シータシペルメトリン(theta-cypermethrin)、タウフルバリネート(tau-fluvalinate)、トラロメスリン(tralomethrin)、プロフルスリン(profluthrin)、ベータシペルメトリン(beta-cypermethrin)、ベータシフルトリン(beta-cyfluthrin)、メトフルトリン(metofluthrin)のようなピレスロイド系化合物;
ジフルベンズロン(diflubenzuron)、クロルフルアズロン(chlorfluazuron)、テフルベンズロン(teflubenzuron)、フルフェノクスロン(flufenoxuron)、ルフェヌロン(lufenuron)、ノバルロン(novaluron)、トリフルムロン(triflumuron)、ヘキサフルムロン(hexaflumuron)、ビストリフルロン(bistrifluron)、ノビフルムロン(noviflumuron)、フルアズロン(fluazuron)のようなベンゾイルウレア系化合物;
メトプレン(methoprene)、ピリプロキシフェン(pyriproxyfen)、フェノキシカルブ(fenoxycarb)、ジオフェノラン(diofenolan)のような幼若ホルモン様化合物;
ピリダベン(pyridaben)のようなピリダジノン系化合物;
フェンピロキシメート(fenpyroximate)、フィプロニル(fipronil)、テブフェンピラド(tebufenpyrad)、エチピロール(ethiprole)、トルフェンピラド(tolfenpyrad)、アセトプロール(acetoprole)、ピラフルプロール(pyrafluprole)、ピリプロール(pyriprole)のようなピラゾール系化合物;
イミダクロプリド(imidacloprid)、ニテンピラム(nitenpyram)、アセタミプリド(acetamiprid)、チアクロプリド(thiacloprid)、チアメトキサム(thiamethoxam)、クロチアニジン(clothianidin)、ニジノテフラン(nidinotefuran)、ジノテフラン(dinotefuran)などのネオニコチノイド;
テブフェノジド(tebufenozide)、メトキシフェノジド(methoxyfenozide)、クロマフェノジド(chromafenozide)、ハロフェノジド(halofenozide)などのヒドラジン系化合物;
ピリダリル(Pyridaryl)、フロニカミド(flonicamid)などのようなピリジン系化合物;
スピロディクロフェン(spirodiclofen)などのようなテトロニック酸系化合物;
フルアクリピリム(fluacrypyrin)などのようなストロビルリン系化合物;
フルフェネリム(flufenerim)などのようなピリジナミン系化合物;
ジニトロ系化合物;有機硫黄化合物;尿素系化合物;トリアジン系化合物;ヒドラゾン系化合物;また、その他の化合物として、ブプロフェジン(buprofezin)、ヘキシチアゾクス(hexythiazox)、アミトラズ(amitraz)、クロルジメホルム(chlordimeform)、シラフルオフェン(silafluofen)、トリアザメイト(triazamate)、ピメトロジン(pymetrozine)、ピリミジフェン(pyrimidifen)、クロルフェナピル(chlorfenapyr)、インドキサカルブ(indoxacarb)、アセキノシル(acequinocyl)、エトキサゾール(etoxazole)、シロマジン(cyromazine)、1,3-ジクロロプロペン(1,3-dichloropropene)、ジアフェンチウロン(diafenthiuron)、ベンクロチアズ(benclothiaz)、フルフェンリム(flufenerim)、ピリダリル(pyridalyl)、スピロジクロフェン(spirodiclofen)、ビフェナゼート(bifenazate)、スピロテトラマット(spirotetramat)、プロパルギット(propargite)、ベルブチン(verbutin)、スピロメシフェン(spiromesifen)、チアゾリルシナノニトリル(thiazolylcinnanonitrile)、アミドフルメット(amidoflumet)、フルベンジアミド(flubendiamide)、クロフェンテジン(clofentezine)メタフルミゾン(metaflumizone)、クロルアントラニルプロール(chlorantraniliprole)、HGW-86、シフルメトフェン(cyflumetofen)、シエノピラフェン(cyenopyrafen)、ピリフルキナゾン(pyrifluquinazone)、フェナザキン(fenazaquin)、ピリダベン(pyridaben)、アミドフルメット(amidoflumet)、クロロベンゾエート(chlorobenzoate)、スルフルアミド(sulfluramid)、メタアルデヒド(metaldehyde)、リアノジン(ryanodine)のような化合物;
AKD‐1022、IKA‐2000などが挙げられる。
更に、Bacillus thuringienses aizawai、Bacillus thuringienses kurstaki、Bacillus thuringienses israelensis、Bacillus thuringienses japonensis、Bacillus thuringienses tenebrionis又はBacillus thuringiensesが生成する結晶タンパク毒素;昆虫病原ウイルス剤、昆虫病原糸状菌剤、線虫病原糸状菌剤などのような微生物農薬;アベルメクチン(avermectin)、ミルベメクチン(milbemectin)、ミルベマイシン(milbemycin)、スピノサッド(spinosad)、エマメクチンベンゾエート(emamectin Benzoate)、イベルメクチン(ivermectin)、レピメクチン(lepimectin)、スピネトラム(spinetoram)、アバメクチン(abamectin)、エマメクチン(emamectin)のような抗生物質;アザディラクチン(azadirachtin)、ロテノン(rotenone)のような天然物;ディート(deet)のような忌避剤などと、混用、併用することもできる。
(1)(a)式(I)で表されるイミダゾール系化合物の少なくとも1種と、(b)ポリオキシンとを有効成分として含有することを特徴とする農園芸用殺菌剤組成物。
(2)(a)式(I)で表されるイミダゾール系化合物の少なくとも1種と、(b)ポリオキシンとの相乗有効量を含有する前記(1)記載の農園芸用殺菌剤組成物。
(3)(a)式(I)で表されるイミダゾール系化合物の少なくとも1種と、(b)ポリオキシンとの重量比が1:10000~10000:1である前記(1)記載の農園芸用殺菌剤組成物。
(4)(a)式(I)で表されるイミダゾール系化合物の少なくとも1種と、(b)ポリオキシンとの重量比が1:1000~1000:1である前記(1)記載の農園芸用殺菌剤組成物。
(5)式(I)で表されるイミダゾール系化合物がシアゾファミドである前記(1)記載の農園芸用殺菌剤組成物。
イネ苗立枯菌(Pythium spinosum)菌糸伸長阻害効果試験
検定に用いる菌株をPSA平板培地で20℃、2日間予備培養し、成育した菌糸の周縁部分を直径4mmのコルクボーラーで打ち抜き、有効成分化合物を所定の濃度含有するように希釈して作成したPDA平板培地上に置いた。本平板培地を20℃で2日間培養したのち菌糸伸長を測定し、阻害率を調べた。
その結果を第1表に示した。
また、コルビーの式により、阻害率の理論値を計算し、第1表の( )内に記載した。実験値がコルビーの式による理論値よりも高い場合に、本発明の農園芸用殺菌剤組成物は、植物病害の防除に関し相乗効果を有する。
芝ピシウム(Pythium graminicola)菌糸伸長阻害効果試験
試験例1と同様の方法で、菌糸伸長を測定し、阻害率を調べ、結果を第2表に示した。なお、無処理区の菌糸伸長平均は46.5mmであった。
(イ)シアゾファミド 2重量部、(ロ)ポリオキシンBを主成分とするポリオキシン複合体 10重量部、(ハ)ナフタレンスルホン酸ナトリウムホルマリン縮合物 5重量部、(ニ)アルキルベンゼンスルホン酸ナトリウム 5重量部、(ホ)クレー 78重量部、以上の各成分を混合し、水和剤を得る。
(イ)シアゾファミド 0.5重量部、(ロ)ポリオキシンBを主成分とするポリオキシン複合体 2.5重量部、(ハ)炭酸カルシウム 20重量部、(ニ)クレー 77重量部、以上の各成分を混合し、粉剤を得る。
なお、本出願は、2008年3月28日付けで出願された日本特許出願(特願2008-085318)及び2008年5月23日付けで出願された日本特許出願(特願2008-135649)に基づいており、その全体が引用により援用される。
また、ここに引用されるすべての参照は全体として取り込まれる。
Claims (5)
- (a)式(I)で表されるイミダゾール系化合物の少なくとも1種と、(b)ポリオキシンとの相乗有効量を含有する請求項1に記載の農園芸用殺菌剤組成物。
- (a)式(I)で表されるイミダゾール系化合物の少なくとも1種と、(b)ポリオキシンとの混合重量比が1:10000~10000:1である請求項1に記載の農園芸用殺菌剤組成物。
- 式(I)で表されるイミダゾール系化合物がシアゾファミドである請求項1に記載の農園芸用殺菌剤組成物。
- 請求項1、2、3又は4に記載の農園芸用殺菌剤組成物を植物に施用することを特徴とする植物病害の防除方法。
Priority Applications (10)
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CA2722038A CA2722038C (en) | 2008-03-28 | 2009-03-27 | Fungicide composition for agriculture and horticulture and method for preventing plant diseases |
RU2010144047/13A RU2484630C2 (ru) | 2008-03-28 | 2009-03-27 | Фунгицидная композиция для сельского хозяйства и садоводства и способ предотвращения заболеваний растений |
MX2010010580A MX2010010580A (es) | 2008-03-28 | 2009-03-27 | Composicion fungicida para agricultura y horticultura y procedimiento para prevenir enfermedades en plantas. |
BRPI0910109-8A BRPI0910109A2 (pt) | 2008-03-28 | 2009-03-27 | Composição fungicida para a agricultura e horticultura a método para prevenir doenças de plantas |
NZ588153A NZ588153A (en) | 2008-03-28 | 2009-03-27 | Fungicide composition for agriculture and horticulture and method for preventing plant diseases |
US12/934,852 US8741859B2 (en) | 2008-03-28 | 2009-03-27 | Fungicide composition for agriculture and horticulture and method for preventing plant diseases |
AU2009229811A AU2009229811B2 (en) | 2008-03-28 | 2009-03-27 | Fungicide composition for agriculture and horticulture and method for preventing plant diseases |
CN200980111204.XA CN101980605B (zh) | 2008-03-28 | 2009-03-27 | 农业和园艺用杀菌剂组合物及用于预防植物病害的方法 |
ZA2010/06701A ZA201006701B (en) | 2008-03-28 | 2010-09-17 | "fungicide composition for agriculture and horticulture and method for preventing plant diseases" |
MA33269A MA32243B1 (fr) | 2008-03-28 | 2010-10-19 | Composition bactéricide destinée à l'agriculture et à l'horticulture et procédé de prévention contre les maladies des plantes |
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JP (1) | JP5502354B2 (ja) |
KR (1) | KR101548403B1 (ja) |
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CA (1) | CA2722038C (ja) |
CO (1) | CO6310996A2 (ja) |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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CN106719740A (zh) * | 2016-11-29 | 2017-05-31 | 德州迈科生物技术有限公司 | 一种含有多抗霉素和苯甲酸钠的杀菌组合物及其应用 |
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JP2012158585A (ja) * | 2011-01-11 | 2012-08-23 | Ishihara Sangyo Kaisha Ltd | 根こぶ病の防除方法 |
JP6351928B2 (ja) * | 2013-03-04 | 2018-07-04 | 片倉コープアグリ株式会社 | 農地及び農地に使用する資材の病原抑止力の評価方法並びに同方法を用いた農作物栽培システム |
CN103444737B (zh) * | 2013-09-29 | 2015-03-04 | 江苏省绿盾植保农药实验有限公司 | 一种含有多抗霉素和苯噻菌胺的杀菌剂组合物 |
CA3092616A1 (en) * | 2018-03-01 | 2019-09-06 | Ishihara Sangyo Kaisha, Ltd. | Pharmaceutical composition with excellent storage stability |
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- 2009-03-27 NZ NZ588153A patent/NZ588153A/en unknown
- 2009-03-27 KR KR1020107021308A patent/KR101548403B1/ko active IP Right Grant
- 2009-03-27 AU AU2009229811A patent/AU2009229811B2/en active Active
- 2009-03-27 MX MX2010010580A patent/MX2010010580A/es active IP Right Grant
- 2009-03-27 CN CN200980111204.XA patent/CN101980605B/zh active Active
- 2009-03-27 TW TW098110154A patent/TWI430748B/zh active
- 2009-03-27 WO PCT/JP2009/056380 patent/WO2009119842A1/ja active Application Filing
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CN106719740A (zh) * | 2016-11-29 | 2017-05-31 | 德州迈科生物技术有限公司 | 一种含有多抗霉素和苯甲酸钠的杀菌组合物及其应用 |
Also Published As
Publication number | Publication date |
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US20110028419A1 (en) | 2011-02-03 |
TWI430748B (zh) | 2014-03-21 |
RU2484630C2 (ru) | 2013-06-20 |
RU2010144047A (ru) | 2012-05-10 |
KR20100125355A (ko) | 2010-11-30 |
TW200942175A (en) | 2009-10-16 |
MY155967A (en) | 2015-12-31 |
MX2010010580A (es) | 2011-02-25 |
MA32243B1 (fr) | 2011-04-01 |
NZ588153A (en) | 2011-11-25 |
TR201007678T1 (tr) | 2010-12-21 |
JP2010001283A (ja) | 2010-01-07 |
CA2722038A1 (en) | 2009-10-01 |
CA2722038C (en) | 2016-03-15 |
ECSP10010501A (es) | 2010-10-30 |
CN101980605B (zh) | 2014-12-03 |
CO6310996A2 (es) | 2011-08-22 |
ZA201006701B (en) | 2011-05-25 |
KR101548403B1 (ko) | 2015-08-28 |
CN101980605A (zh) | 2011-02-23 |
JP5502354B2 (ja) | 2014-05-28 |
AU2009229811B2 (en) | 2013-07-11 |
BRPI0910109A2 (pt) | 2015-09-01 |
US8741859B2 (en) | 2014-06-03 |
AU2009229811A1 (en) | 2009-10-01 |
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