AU2016102057B4 - Water dispersible granule containing azoxystrobin and cyproconazole and preparation method thereof - Google Patents
Water dispersible granule containing azoxystrobin and cyproconazole and preparation method thereof Download PDFInfo
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- AU2016102057B4 AU2016102057B4 AU2016102057A AU2016102057A AU2016102057B4 AU 2016102057 B4 AU2016102057 B4 AU 2016102057B4 AU 2016102057 A AU2016102057 A AU 2016102057A AU 2016102057 A AU2016102057 A AU 2016102057A AU 2016102057 B4 AU2016102057 B4 AU 2016102057B4
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- Australia
- Prior art keywords
- cyproconazole
- water dispersible
- azoxystrobin
- dispersible granule
- water
- Prior art date
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- 239000005757 Cyproconazole Substances 0.000 title claims abstract description 65
- 239000004562 water dispersible granule Substances 0.000 title claims abstract description 62
- UFNOUKDBUJZYDE-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC(Cl)=CC=1)C(C)C1CC1 UFNOUKDBUJZYDE-UHFFFAOYSA-N 0.000 title claims abstract description 41
- 239000005730 Azoxystrobin Substances 0.000 title claims abstract description 41
- WFDXOXNFNRHQEC-GHRIWEEISA-N azoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1OC1=CC(OC=2C(=CC=CC=2)C#N)=NC=N1 WFDXOXNFNRHQEC-GHRIWEEISA-N 0.000 title claims abstract description 41
- 238000002360 preparation method Methods 0.000 title description 8
- 239000002270 dispersing agent Substances 0.000 claims abstract description 37
- 239000000080 wetting agent Substances 0.000 claims abstract description 37
- 150000008051 alkyl sulfates Chemical class 0.000 claims abstract description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000000945 filler Substances 0.000 claims abstract description 14
- 239000000843 powder Substances 0.000 claims description 28
- 239000000463 material Substances 0.000 claims description 18
- 238000001125 extrusion Methods 0.000 claims description 14
- 238000005469 granulation Methods 0.000 claims description 14
- 230000003179 granulation Effects 0.000 claims description 14
- 238000000227 grinding Methods 0.000 claims description 14
- 238000004898 kneading Methods 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 10
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 8
- 229930006000 Sucrose Natural products 0.000 claims description 8
- 239000005720 sucrose Substances 0.000 claims description 8
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- 229960000892 attapulgite Drugs 0.000 claims description 3
- 239000000440 bentonite Substances 0.000 claims description 3
- 229910000278 bentonite Inorganic materials 0.000 claims description 3
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 claims description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 239000008103 glucose Substances 0.000 claims description 3
- 229910052625 palygorskite Inorganic materials 0.000 claims description 3
- 239000000377 silicon dioxide Substances 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000000454 talc Substances 0.000 claims description 3
- 229910052623 talc Inorganic materials 0.000 claims description 3
- 239000005995 Aluminium silicate Substances 0.000 claims description 2
- 229920002261 Corn starch Polymers 0.000 claims description 2
- 235000012211 aluminium silicate Nutrition 0.000 claims description 2
- 239000008120 corn starch Substances 0.000 claims description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims 1
- 229920001732 Lignosulfonate Polymers 0.000 abstract description 17
- 239000008233 hard water Substances 0.000 abstract description 12
- 239000000575 pesticide Substances 0.000 abstract description 8
- 239000003795 chemical substances by application Substances 0.000 abstract description 6
- 229940051841 polyoxyethylene ether Drugs 0.000 description 10
- 229920000056 polyoxyethylene ether Polymers 0.000 description 10
- 159000000000 sodium salts Chemical class 0.000 description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 239000004557 technical material Substances 0.000 description 8
- 241000221785 Erysiphales Species 0.000 description 7
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- JSYPRLVDJYQMAI-ODZAUARKSA-N (z)-but-2-enedioic acid;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)\C=C/C(O)=O JSYPRLVDJYQMAI-ODZAUARKSA-N 0.000 description 6
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 229920005646 polycarboxylate Polymers 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 5
- 229920005552 sodium lignosulfonate Polymers 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 4
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- KKDONKAYVYTWGY-UHFFFAOYSA-M sodium;2-(methylamino)ethanesulfonate Chemical compound [Na+].CNCCS([O-])(=O)=O KKDONKAYVYTWGY-UHFFFAOYSA-M 0.000 description 4
- LWEAHXKXKDCSIE-UHFFFAOYSA-M 2,3-di(propan-2-yl)naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S([O-])(=O)=O)=C(C(C)C)C(C(C)C)=CC2=C1 LWEAHXKXKDCSIE-UHFFFAOYSA-M 0.000 description 3
- 235000017060 Arachis glabrata Nutrition 0.000 description 3
- 244000105624 Arachis hypogaea Species 0.000 description 3
- 235000010777 Arachis hypogaea Nutrition 0.000 description 3
- 235000018262 Arachis monticola Nutrition 0.000 description 3
- 229920001400 block copolymer Polymers 0.000 description 3
- 235000013339 cereals Nutrition 0.000 description 3
- 229940043264 dodecyl sulfate Drugs 0.000 description 3
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 3
- 150000002193 fatty amides Chemical class 0.000 description 3
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 235000020232 peanut Nutrition 0.000 description 3
- 206010059866 Drug resistance Diseases 0.000 description 2
- 229920005682 EO-PO block copolymer Polymers 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 241001123583 Puccinia striiformis Species 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 235000009754 Vitis X bourquina Nutrition 0.000 description 2
- 235000012333 Vitis X labruscana Nutrition 0.000 description 2
- 240000006365 Vitis vinifera Species 0.000 description 2
- 235000014787 Vitis vinifera Nutrition 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 230000004075 alteration Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 230000002085 persistent effect Effects 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 241001480061 Blumeria graminis Species 0.000 description 1
- 239000005747 Chlorothalonil Substances 0.000 description 1
- 241000233652 Chytridiomycota Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 241000233679 Peronosporaceae Species 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 1
- 206010039509 Scab Diseases 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 229930182692 Strobilurin Natural products 0.000 description 1
- 239000005842 Thiophanate-methyl Substances 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 238000012271 agricultural production Methods 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000011859 microparticle Substances 0.000 description 1
- LCRMGUFGEDUSOG-UHFFFAOYSA-N naphthalen-1-ylsulfonyloxymethyl naphthalene-1-sulfonate;sodium Chemical compound [Na].C1=CC=C2C(S(=O)(OCOS(=O)(=O)C=3C4=CC=CC=C4C=CC=3)=O)=CC=CC2=C1 LCRMGUFGEDUSOG-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- 239000003090 pesticide formulation Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- -1 succinate sulfonic acid sodium salt Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000006277 sulfonation reaction Methods 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
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 235000013311 vegetables Nutrition 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/12—Powders or granules
- A01N25/14—Powders or granules wettable
-
- 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
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The present invention relates to the technical field of pesticides, discloses a water dispersible granule containing azoxystrobin and cyproconazole. The water dispersible granule of the invention consists of azoxystrobin, cyproconazole, the dispersing agent lignosulfonate, the wetting agent alkylsulfate and a filler. A water dispersible granule which attains better disintegrating and suspending properties and lower foamability in high concentration of hard water is prepared in the present invention by adjusting the type of auxiliaries of the water dispersible granule with respect to the agent characteristics of azoxystrobin and cyproconazole, and only using specific dispersing agent, wetting agent and filler in combination, which is particularly suitable for countries and regions of higher water hardness.
Description
1 2016102057 30 Nov 2016
WATER DISPERSIBLE GRANULE CONTAINING AZOXYSTROBIN AND CYPROCONAZOLE AND PREPARATION METHOD THEREOF 5 Field of the invention
The present invention relates to the technical field of pesticides, and particularly to a water dispersible granule containing azoxystrobin and cyproconazole and preparation method thereof. 10 Background of the invention
In the field of agricultural production, the problems of drug resistance of germs easily occur in the process of disease control, such as the powdery mildew in agriculture which often rises in the late growth stage of cucurbit crops due to its high speed of spreading and wide range of hosts, and is particularly easy to develop a 15 resistance. Another example is that in some places with serious harm of powdery mildew, the common fungicides such as chlorothalonil, thiophanate-methyl have no effect when used alone, and triadimefon or the like has also caused a serious resistance due to large area of application, and is prone to generate phytotoxicity. Therefore, existing pesticides often employ a combination of multiple active 20 ingredients, to achieve better control effect by means of synergism, while are not prone to drug resistance.
Azoxystrobin is a strobilurin fungicide, which has a high efficacy and broad spectrum, and has good activities on almost all diseases caused by kingdom fungi (Ascomycotina, Basidiomycotina, Mastigomycotina and Deuteromycotina), such as 25 powdery mildew, rust disease, glume blight, net blotch, downy mildew, rice blast, etc. It can be used for stem and leaf spray, seed treatment, and also soil treatment, and is mainly used for cereal, rice, peanut, grape, potato, fruit tree, vegetable, coffee, lawn and the like; cyproconazole is mainly used to control rust disease of cereals and coffee, powdery mildew of cereals, fruit tree and grape, leaf spot disease of peanut 30 and beet, apple scab and white rot of peanut. In the prior art, they are combined to prepare into pesticide formulations for controlling crop diseases.
Among a large variety of pesticide dosage forms, in addition to the features of 2 2016102057 30 Nov 2016 the general granules, water dispersible granules further exhibit the following characteristics: (1) no dust flying, thus reducing the pollution to the environment, being safe to the operator, and can make highly toxic species modified to low toxicity; (2) having a higher content of active ingredient, larger relative density of product, 5 smaller volume and convenience for packing, storing and transporting as compared to wettable powders and suspensions; (3) having a better storage stability and physical-chemical stability, particularly for unstable pesticides in water which is better to be made into such a dosage form than the suspension; (4) a fast disintegration speed of the granules, wherein the granules are immediately wetted 10 upon contacted with water, and disintegrated rapidly in the process of submerging; (5) dispersing of the granules into very small particles rapidly after disintegrated in water, of which after disintegration, agitation, and wet-screened through 325-mesh sieve, the residue on the sieve should not be greater than 0.3%; (6) better suspension stability, by which the agent liquid that is formulated but not used up on the day can be 15 re-suspended the next day after stirring, without affecting the efficacy; (7) only slightly agitation is required for the granules to be dispersed in the liquid so that the fine microparticles can be well dispersed in the liquid which can maintain homogeneity until all the drug liquid is sprayed.
In general, the water dispersible granule consists of an active gradient, a 20 wetting agent, a dispersing agent, a disintegrating agent, a stabilizing agent, a binder and a carrier, while the wetting-dispersing property and disintegrating property are important indicators for water dispersible granules. Both the China Patent Nos. CN102047889A and CN102907433A disclose a sterilizing composition containing azoxystrobin and cyproconazole, and specifically disclose a technical solution of a 25 water dispersible granule of azoxystrobin and cyproconazole, wherein the auxiliaries employed are dispersing agent, wetting agent, disintegrating agent and filler, etc. According to the description, these water dispersible granules have good physicochemical properties and control effects, however, it is discovered after examination that the beneficial effects of these water dispersible granules in various 30 aspects are only suitable for countries and regions having not very high water hardness, while adoption of the above described water dispersible granules in countries having commonly high concentration of hard water such as Australia will exhibit phenomena of poor product qualities, such as poorer disintegrating and suspending properties, and higher foamability, which prevents the complete exertion 35 of the efficacies of azoxystrobin and cyproconazole. 2016102057 18 May 2017 3
Summary of the invention
In view of this, it would be desirable to provide a water dispersible granule containing azoxystrobin and cyproconazole and preparation method thereof, so that 5 the water dispersible granule has better disintegrating and suspending properties and a lower foamability under conditions of high hard water concentration.
Accordingly, the present invention provides the following technical solutions: A water dispersible granule containing azoxystrobin and cyproconazole, consisting of azoxystrobin, cyproconazole, a dispersing agent, a wetting agent and a 10 filler; the dispersing agent is selected from the group consisting of: (1) lignosulfonate; (2) polycarboxylate, ethylene oxide-propylene oxide block copolymer; (3) maleic acid-acrylic acid copolymer, arylphenol polyoxyethylene ether; 15 (4) alkylnaphthalenesulfonic acid sodium salt, alkylnaphthalenesulfonic acid formaldehyde condensate sodium salt; (5) polyoxy ethyl ene-polyoxypropylene block copolymer, alkylphenol polyoxyethylene polyoxypropylene ether; (6) alkylphenolsulfonate; 20 (7) maleic acid-acrylic acid copolymer, polycarboxylate; the wetting agent is selected from the group consisting of: (1) alkylsulfate; (2) fatty amide N-methyl taurine sodium salt; (3) Nekal, laurylsulfate; 25 (4) alkylphenol polyoxyethylene ether sulfate, sodium oalkenyl sulfonate; (5) naphthalenesulfonic acid formaldehyde condensate sodium salt, dodecylbenzenesul fonate; 4 2016102057 30 Nov 2016 (6) α-sulfofatty acid methyl ester, alkylsulfate; (7) lauryl sulfuric acid, alkylphenol polyoxyethylene ether sulfate.
Aiming at the problem that the prior water dispersible granule of azoxystrobin and cyproconazole is unable to achieve a better product performance in the 5 environment of high concentration of hard water, the selection criteria of conventional auxiliaries of water dispersible granule is adjusted by the present invention, with the frequently used disintegrating agents removed, and prepared only with the dispersing agent lignosulfonate , the wetting agent alkylsulfate and a filler, to achieve a better product performance in high concentration of hard water. 10 Wherein, as a preference, by weight percentage, the azoxystrobin is l%-60%, the cyproconazole is l%-39%, the dispersing agent is 6%-15%, the wetting agent is 2.5%-6%, and the balance of the filler to 100%.
More preferably, the weight percent of azoxystrobin can be specifically selected to be 1%, 10%, 16%, 34%, 35%, 40%, 58%, 60% or 64%; the weight percent 15 of cyproconazole can be specifically selected to be 1%, 2%, 4%, 10%, 16%, 20%, 24%, 35% or 39%.
More preferably, the dispersing agent is selected from the group consisting of: (1) 10% of lignosulfonate; (2) 4% of polycarboxylate, 4% of ethylene oxide-propylene oxide block 20 copolymer; (3) 7% of maleic acid-acrylic acid copolymer, 8% of arylphenol polyoxyethylene ether; (4) 4% of alkylnaphthalenesulfonic acid sodium salt, 2% of alkylnaphthalenesulfonic acid formaldehyde condensate sodium salt; 25 (5) 6% of polyoxyethylene-polyoxypropylene block copolymer, 7% of alkylphenol polyoxyethylene polyoxypropylene ether; (6) 12% of alkylphenolsulfonate; or (7) 5% of maleic acid-acrylic acid copolymer, 4% of polycarboxylate; the wetting agent is selected from the group consisting of: 30 (1) 2.5% of alkylsulfate; (2) 3% of fatty amide N-methyl taurine sodium salt; 5 2016102057 30 Nov 2016 (3) 2% of Nekal, 2.5% of laurylsulfate; (4) 1.5% of alkylphenol polyoxyethylene ether sulfate, 3.5% sodium a-alkenyl sulfonate; (5) 3% of naphthalenesulfonic acid formaldehyde condensate sodium salt, 1.5% of 5 dodecylbenzenesulfonate; (6) 3% of α-sulfofatty acid methyl ester, 3% of alkylsulfate; or (7) 2% of lauryl sulfuric acid, 2% of alkylphenol polyoxyethylene ether sulfate.
As a preference, the lignosulfonate is sodium lignosulfonate. In a specific embodiment of the present invention, the dispersing agent sodium lignosulfonate can 10 be further selected to be the dispersing agent sodium lignosulfonate REAX 907, which has a higher molecular weight and a lower sulfonation degree.
As a preference, the wetting agent alkylsulfate is the wetting agent alkylsulfate REAX WL. In a specific embodiment of the present invention, the product performance with best effect can be achieved by employing the dispersing agent 15 sodium lignosulfonate REAX 907 and the wetting agent alkylsulfate REAX WL in combination.
As a preference, the filler is one or more of kaolin, attapulgite, diatomite, organic bentonite, precipitated silica, light calcium carbonate, com starch, glucose, talc and anhydrous sodium sulfate. 20 In the specific process of implementation, the present invention also provides a water dispersible granule with a specific formulation, wherein every 1000 g of the water dispersible granule consists of 612.2 g of azoxystrobin technical material, 250 g of cyproconazole technical material, 100 g of the dispersing agent lignosulfonate, 25 g of the wetting agent alkylsulfate and 12.8 g of a filler. In the specific process of 25 implementation, the purity of the azoxystrobin technical material is 98%, and the purity of the cyproconazole technical material is 96%.
Meanwhile, the present invention further provides a method for preparing the water dispersible granule, comprising homogeneously mixing azoxystrobin, cyproconazole, the dispersing agent, the wetting agent and the filler, conducting 30 ultramicro airflow grinding, adding the resultant fine powder with water to perform kneading, and then subjecting the kneaded material to extrusion granulation and drying, to obtain the water dispersible granule. 6 2016102057 30 Nov 2016
Wherein, the mesh number of the fine powder is preferably 680-840 mesh, and the temperature for drying is 30-70 °C.
By comparing the dispersing property, foamability, disintegrating property and suspension rate in high concentration of hard water of the water dispersible granule 5 according to the present invention as well as the product of Example 1 in the prior patent CN102047889A and the products of Example 1-13 in CN102907433A, the results show that, the dispersing property, disintegrating property and suspension rate of the water dispersible granule according to the present invention is significantly superior to those of the products in the prior patents, the foamability of the water 10 dispersible granule according to the present invention is significantly lower than that of the products in the prior patents, and phenomena of unqualification exist in the products in the prior patents.
Meanwhile, those which are different from the dispersing agent lignosulfonate and the wetting agent alkylsulphate used in the present invention are selected for 15 comparative test in the present invention, and the results show that, the superior product performance can be exhibited in the environment of high concentration of hard water only on the premise of the selected auxiliaries of the present invention, particularly in combination of the dispersing agent sodium lignosulfonate REAX 907 and the wetting agent alkylsulfate REAX WL, in which the product performance with 20 the best effect can be achieved.
It can be known from the technical solutions above that, a water dispersible granule which attains better disintegrating property and suspension rate and lower foamability in high concentration of hard water is prepared in the present invention by adjusting the type of auxiliaries of the water dispersible granule with respect to the 25 agent characteristics of azoxystrobin and cyproconazole, and only using specific dispersing agent, wetting agent and filler in combination, which is particularly suitable for countries and regions of higher water hardness.
Detailed embodiments 30 The embodiments of the present invention disclose a water dispersible granule containing azoxystrobin and cyproconazole and preparation method thereof, which can be achieve by those skilled in the art by using the content herein for reference and suitably improving the process parameters. It should be particularly noted that all similar alternatives and alterations will be apparent to those skilled in the art, and are 7 2016102057 30 Nov 2016 all considered to be included within the present invention. The water dispersible granule and preparation method thereof of the present invention have been described by way of preferred embodiments and it is apparent that the related personnel can achieve and apply the techniques of the present invention by alterations or proper 5 modifications and combinations of the products and methods described herein, without departing from the content, spirit and scope of the preset invention.
All the technical materials or auxiliaries used in the water dispersible granule of azoxystrobin and cyproconazole and preparation method thereof provided by the present invention are commercially available. Wherein, the lignosulfonate REAX907 10 is purchased from MeadWestvaco, and the alkylsulfate WL is purchased from MeadWestvaco.
In the specific process of implementation, the active ingredients of the formulation are all prepared with the technical materials, wherein the purity of the azoxystrobin technical material is 98%, and the purity of the cyproconazole technical 15 material is 96%; the weight percentage can be converted into specific weight units such as grams, kilograms, etc. according to the purity of the technical materials. Taking Example 1 for example, every 1000 g of the water dispersible granule consists of 612.2 g of azoxystrobin technical material, 250 g of cyproconazole technical material, 100 g of the dispersing agent lignosulfonate, 25 g of the wetting agent 20 alkylsulfate and 12.8 g of sucrose (filler), wherein the percentages by weight as converted are the respective percentages as described in Example 1. This also applies to the other Examples.
The water dispersible granule containing azoxystrobin and cyproconazole and preparation method thereof provided by the present invention are further illustrated as 25 follows.
Example 1: Water dispersible granule of 84% azoxystrobin-cyproconazole 60% of azoxystrobin, 24% of cyproconazole, 10% of the dispersing agent lignosulfonate REAX907 (MeadWestvaco), 2.5% of the wetting agent alkylsulfate 30 WL (MeadWestvaco) and the balance of sucrose to 100% were homogeneously mixed, and then ultramicro airflow grinding was conducted to obtain a fine powder of 700 mesh; the obtained fine powders were added with water to perform kneading, then the kneaded material was subjected to extrusion granulation and dried at 55 °C, to obtain the water dispersible granule of 84% azoxystrobin-cyproconazole. 8 2016102057 30 Nov 2016
Example 2: Water dispersible granule of 70% azoxystrobin-cyproconazole 35% of azoxystrobin, 35% of cyproconazole, 10% of the dispersing agent lignosulfonate REAX907 (MeadWestvaco), 2.5% of the wetting agent alkylsulfate 5 WL (MeadWestvaco) and the balance of sucrose to 100% were homogeneously mixed, and then ultramicro airflow grinding was conducted to obtain a fine powder of 750 mesh; the obtained fine powders were added with water to perform kneading, then the kneaded material was subjected to extrusion granulation and dried at 52 °C, to obtain the water dispersible granule of 70% azoxystrobin-cyproconazole. 10
Example 3: Water dispersible granule of 50% azoxystrobin-cyproconazole 40% of azoxystrobin, 10% of cyproconazole, 10% of the dispersing agent lignosulfonate REAX907 (MeadWestvaco), 2.5% of the wetting agent alkylsulfate WL (MeadWestvaco) and the balance of sucrose to 100% were homogeneously mixed, 15 and then ultramicro airflow grinding was conducted to obtain a fine powder of 720 mesh; the obtained fine powders were added with water to perform kneading, then the kneaded material was subjected to extrusion granulation and dried at 50 °C, to obtain the water dispersible granule of 50% azoxystrobin-cyproconazole. 20 Example 4: Water dispersible granule of 30% azoxystrobin-cyproconazole 10% of azoxystrobin, 20% of cyproconazole, 10% of the dispersing agent lignosulfonate REAX907 (MeadWestvaco), 2.5% of the wetting agent alkylsulfate WL (MeadWestvaco) and the balance of sucrose to 100% were homogeneously mixed, and then ultramicro airflow grinding was conducted to obtain a fine powder of 680 25 mesh; the obtained fine powders were added with water to perform kneading, then the kneaded material was subjected to extrusion granulation and dried at 45 °C, to obtain the water dispersible granule of 30% azoxystrobin-cyproconazole.
Example 5: Water dispersible granule of 60% azoxystrobin-cyproconazole 30 58% of azoxystrobin, 2% of cyproconazole, 10% of the dispersing agent lignosulfonate REAX907 (MeadWestvaco), 2.5% of the wetting agent alkylsulfate WL (MeadWestvaco) and the balance of sucrose to 100% were homogeneously mixed, 9 2016102057 30 Nov 2016 and then ultramicro airflow grinding was conducted to obtain a fine powder of 730 mesh; the obtained fine powders were added with water to perform kneading, then the kneaded material was subjected to extrusion granulation and dried at 48 °C, to obtain the water dispersible granule of 60% azoxystrobin-cyproconazole. 5
Example 6: Water dispersible granule of 40% azoxystrobin-cyproconazole 1% of azoxystrobin, 39% of cyproconazole, 10% of the dispersing agent lignosulfonate REAX907 (MeadWestvaco), 2.5% of the wetting agent alkylsulfate WL (MeadWestvaco) and the balance of sucrose to 100% were homogeneously mixed, 10 and then ultramicro airflow grinding was conducted to obtain a fine powder of 750 mesh; the obtained fine powders were added with water to perform kneading, then the kneaded material was subjected to extrusion granulation and dried at 46 °C, to obtain the water dispersible granule of 40% azoxystrobin-cyproconazole. 15 Example 7: Water dispersible granule of 84% azoxystrobin-cyproconazole 60% of azoxystrobin, 24% of cyproconazole, 4% of the dispersing agent polycarboxylate, 4% of ethylene oxide-propylene oxide block copolymer, 3% of the wetting agent fatty amide N-methyl taurine sodium salt and the balance of com starch to 100% were homogeneously mixed, and then ultramicro airflow grinding was 20 conducted to obtain a fine powder of 780 mesh; the obtained fine powders were added with water to perform kneading, then the kneaded material was subjected to extrusion granulation and dried at 55 °C, to obtain the water dispersible granule of 84% azoxystrobin-cyproconazole. 25 Example 8: Water dispersible granule of 56% azoxystrobin-cyproconazole 40% of azoxystrobin, 16% of cyproconazole, 7% of the dispersing agent maleic acid-acrylic acid copolymer, 8% of arylphenol polyoxyethylene ether, 2% of the wetting agent Nekal, 2.5% of laurylsulfate, 10% of anhydrous sodium sulfate and the balance of diatomite to 100% were homogeneously mixed, and then ultramicro 30 airflow grinding was conducted to obtain a fine powder of 760 mesh; the obtained fine powders were added with water to perform kneading, then the kneaded material was subjected to extrusion granulation and dried at 50 °C, to obtain the water dispersible granule of 56% azoxystrobin-cyproconazole. ίο 2016102057 30 Nov 2016
Example 9: Water dispersible granule of 20% azoxystrobin-cyproconazole 16% of azoxystrobin, 4% of cyproconazole, 4% of the dispersing agent alkylnaphthalenesulfonic acid sodium salt, 2% of alkylnaphthalenesulfonic acid 5 formaldehyde condensate sodium salt, 1.5% of the wetting agent alkylphenol polyoxyethylene ether sulfate, 3.5% of sodium α-alkenyl sulfonate, 40% of organic bentonite and the balance of light calcium carbonate to 100% were homogeneously mixed, and then ultramicro airflow grinding was conducted to obtain a fine powder of 700 mesh; the obtained fine powders were added with water to perform kneading, 10 then the kneaded material was subjected to extrusion granulation and dried at 60 °C, to obtain the water dispersible granule of 20% azoxystrobin-cyproconazole.
Example 10: Water dispersible granule of 70% azoxystrobin-cyproconazole 35% of azoxystrobin, 35% of cyproconazole, 6% of the dispersing agent 15 polyoxyethylene-polyoxypropylene block copolymer, 7% of alkylphenol polyoxyethylene ether, 3% of the wetting agent naphthalenesulfonic acid formaldehyde condensate sodium salt, 1.5% of dodecylbenzenesulfonate, 5% of precipitated silica and the balance of talc to 100% were homogeneously mixed, and then ultramicro airflow grinding was conducted to obtain a fine powder of 780 mesh; 20 the obtained fine powders were added with water to perform kneading, then the kneaded material was subjected to extrusion granulation and dried at 50 °C, to obtain the water dispersible granule of 70% azoxystrobin-cyproconazole.
Example 11: Water dispersible granule of 35% azoxystrobin-cyproconazole 25 34% of azoxystrobin, 1% of cyproconazole, 12% of the dispersing agent alkylphenolsulfonate, 3% the wetting agent α-sulfofatty acid methyl ester, 3% of alkylsulfate, 30% of diatomite and the balance of attapulgite to 100% were homogeneously mixed, and then ultramicro airflow grinding was conducted to obtain a fine powder of 750 mesh; the obtained fine powders were added with water to 30 perform kneading, then the kneaded material was subjected to extrusion granulation and dried at 65 °C, to obtain the water dispersible granule of 35% azoxystrobin- cyproconazole. 11 2016102057 30 Nov 2016
Example 12: Water dispersible granule of 65% azoxystrobin-cyproconazole 64% of azoxystrobin, 1% of cyproconazole, 5% of the dispersing agent maleic acid-acrylic acid copolymer, 4% of polycarboxylate, 2% of the wetting agent laurylsulfuric acid, 2% of alkylphenol polyoxyethylene ether sulfate, 10% of glucose 5 and the balance of corn starch to 100% were homogeneously mixed, and then ultramicro airflow grinding was conducted to obtain a fine powder of 800 mesh; the obtained fine powders were added with water to perform kneading, then the kneaded material was subjected to extrusion granulation and dried at 52 °C, to obtain the water dispersible granule of 65% azoxystrobin-cyproconazole. 10
Example 13: Comparative test
Control: 1. The product of Example 1 in CN102047889A (hereinafter abbreviated as CN1); the products of Examples 1-13 in CN102907433A (hereinafter abbreviated as CN2-14). 15 2. Substitution of the dispersing agent lignosulfonate and the wetting agent alkylsulfate to the ones other than those used in the present invention based on the formulation of Example 1, with the same amount, respectively as: the dispersing agent sodium methylene bis-naphthalene sulfonate and the wetting agent dialkyl succinate sulfonic acid sodium salt (hereinafter abbreviated as control 2). 20 3. Substitution of the dispersing agent lignosulfonate to the ones other than REAX 907 and the wetting agent alkylsulfate to the ones other than REAX WL based on the formulations of Example 1, with the same amount, respectively as: the dispersing agent RE ΑΧ 88B and the wetting agent sodium dodecyl sulfate (hereinafter abbreviated as control 1). 25 The performance index test was conducted on all of the Example products in the present invention and the above 3 types of controls in the same high concentration of hard water (3 times of D water, hardness of 1026 mg/L, pH=6.0-7.0, Ca2+:Mg2+=4:l), which refers to the methods provided in “Physical-Chemical Method of Pesticide Technical Material and Formulation - CIPAC Handbook”, and the quality 30 standard refers to “FAO Pesticide Standard Setting and User Manual” and “Guidelines on Drafting Specifications of Water Dispersible Granule of Pesticides”, as specifically shown in Table 1.
Table 1. Comparison of the performance indicators of the Examples in the patents and 12 2016102057 30 Nov 2016 controls Examples Disintegrati ng , s Suspensibility of 3 times of D water, % Persistent foam, mL Wet sieve test (400 mesh) 1 40 98.5 5 99.9 2 42 96.0 7 99.9 3 44 95.3 7 99.9 4 48 96.2 6 99.9 5 50 95.8 5 99.9 6 48 95.0 6 99.9 7 52 91.6 10 99.3 8 48 91.0 12 99.4 9 56 89.6 14 99.2 10 58 89.1 12 99.1 11 57 87.5 16 99.0 12 55 88.7 18 99.0 CN1 56 71.5 45 99.0 CN2 45 80.9 20 99.9 CN3 55 79.8 30 99.9 CN4 49 79.1 23 99.9 CN5 50 79.9 24 99.9 CN6 52 79.3 28 99.9 CN7 60 76.8 35 99.6 CN8 62 77.1 30 99.5 CN9 64 76.5 36 99.4 CN10 68 76.0 36 99.2 CN11 68 76.3 40 99.2 CN12 62 75.8 42 99.0 CN13 64 75.2 42 99.0 13 CN14 64 74.5 32 99.0 Control 1 74 70.1 60 99.0 Control 2 54 82.0 18 99.3 2016102057 30 Nov 2016
As can be seen from the above table, the products of each Example of the present invention can simultaneously achieve better disintegrating and suspensibility as well as persistent foam in the conditions of high concentration of hard water, 5 particularly the products of Examples 1-6 which have the best effects.
Example 14: Efficacy test
The efficacy test was conducted with the products of Examples 1-12 of the present invention in Australia (high concentration of hard water). They were used on 10 barley crops in South Australia to control powdery mildew (Blumeria graminis f sp. hordei), and used on winter wheat in New South Wales to control stripe rust (Puccinia striiformis), with the dosage of 133 g a.i/ha (80 g of azoxystrobin, 32 g of cyproconazole); the control groups are Example 1 in CN102047889A and Example 1 in CN102907433A. The results are shown in Table 2. 15
Table 2. Efficacy comparison (21 days after administration)
Examples Control efficacy on powdery mildew, % Control efficacy on stripe rust, % 1 97.2 96.5 2 94.3 93.1 3 93.9 93.6 4 94.0 93.9 5 92.8 92.5 6 93.1 92.7 7 89.3 88.8 8 89.0 88.7 9 85.6 84.2 14 10 85.9 85.1 11 82.9 83.4 12 83.0 83.8 Example 1 in CN102907433A 78.3 78.1 Example 1 in CN102047889A 73.8 73.1 Clean water control 0 0 2016102057 30 Nov 2016
As can be known from the above table, the products of each Example of the present invention have significantly superior controlling efficacy on powdery mildew and stripe rust of wheat to the products of prior patents in conditions of high 5 concentration of hard water, particularly the products of Examples 1-6 which have the best controlling efficacy.
The foregoing description is only for understanding the method of the present invention and the core concept thereof, and it should be noted to an ordinary skilled in the art that a number of improvements and modifications can be made to the present 10 invention without departing from the principles of the invention, these improvements and modifications also fall within the protection scope of the present invention.
Claims (4)
- CLAIMS:1. A water dispersible granule containing azoxystrobin and cyproconazole, consisting by weight percentage, 1% to 60% of azoxystrobin, 1 to 39% of cyproconazole, 10% of Hgnosulfonate as a dispersing agent, 2.5% of alkylsulfate as a wetting agent, and the balance of a filler to 100%.
- 2. The water dispersible granule according to claim 1, wherein the hgnosulfonate is the dispersing agent sodium hgnosulfonate REAX 907, and the alkylsulfate is the wetting agent alkylsulfate REAX WL.
- 3. The water dispersible granule according to claim 1, wherein the filler is one or more of kaolin, attapulgite, diatomite, organic bentonite, precipitated silica, light calcium carbonate, corn starch, glucose, sucrose, talc and anhydrous sodium sulfate.
- 4. A method for preparing the water dispersible granule of claim 1, comprising homogeneously mixing azoxystrobin, cyproconazole, the dispersing agent, the wetting agent and the filler, conducting ultramicro airflow grinding, adding the resultant fine powder with water to perform kneading, and then subjecting the kneaded material to extrusion granulation and drying, to obtain the water dispersible granule.
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| CN101692807A (en) * | 2009-10-20 | 2010-04-14 | 陕西上格之路生物科学有限公司 | Dispersible oil suspension agent containing cyproconazole |
| CN101697729A (en) * | 2009-11-03 | 2010-04-28 | 成都皇牌作物科学有限公司 | Disinfectant compound containing cyproconazole |
| CN101911940A (en) * | 2010-09-08 | 2010-12-15 | 吴元林 | Germicide compounded from azoxystrobin, difenoconazole and cyproconazole and preparation method thereof |
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| CN102047889A (en) * | 2009-10-29 | 2011-05-11 | 青岛海利尔药业有限公司 | Antibacterial composition containing azoxystrobin and cyproconazole and application thereof |
| CN102907433A (en) * | 2012-10-26 | 2013-02-06 | 山东潍坊润丰化工有限公司 | Sterilization composition containing azoxystrobin and cyproconazole and application of sterilization composition |
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| CN101692807A (en) * | 2009-10-20 | 2010-04-14 | 陕西上格之路生物科学有限公司 | Dispersible oil suspension agent containing cyproconazole |
| CN101697729A (en) * | 2009-11-03 | 2010-04-28 | 成都皇牌作物科学有限公司 | Disinfectant compound containing cyproconazole |
| CN101911940A (en) * | 2010-09-08 | 2010-12-15 | 吴元林 | Germicide compounded from azoxystrobin, difenoconazole and cyproconazole and preparation method thereof |
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