AU2016101530B4 - Water soluble granule of prothioconazole-tebuconazole and preparation method thereof - Google Patents
Water soluble granule of prothioconazole-tebuconazole and preparation method thereof Download PDFInfo
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- AU2016101530B4 AU2016101530B4 AU2016101530A AU2016101530A AU2016101530B4 AU 2016101530 B4 AU2016101530 B4 AU 2016101530B4 AU 2016101530 A AU2016101530 A AU 2016101530A AU 2016101530 A AU2016101530 A AU 2016101530A AU 2016101530 B4 AU2016101530 B4 AU 2016101530B4
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- Australia
- Prior art keywords
- prothioconazole
- tebuconazole
- water dispersible
- dispersible granule
- agent
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- 239000005839 Tebuconazole Substances 0.000 title claims abstract description 80
- 238000002360 preparation method Methods 0.000 title abstract description 8
- 239000004549 water soluble granule Substances 0.000 title description 2
- 239000004562 water dispersible granule Substances 0.000 claims abstract description 58
- MNHVNIJQQRJYDH-UHFFFAOYSA-N 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound N1=CNC(=S)N1CC(C1(Cl)CC1)(O)CC1=CC=CC=C1Cl MNHVNIJQQRJYDH-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000005825 Prothioconazole Substances 0.000 claims abstract description 34
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 32
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000002738 chelating agent Substances 0.000 claims abstract description 24
- 239000002270 dispersing agent Substances 0.000 claims abstract description 24
- 239000000080 wetting agent Substances 0.000 claims abstract description 24
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims abstract description 21
- 201000010099 disease Diseases 0.000 claims abstract description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000000945 filler Substances 0.000 claims abstract description 13
- 241000221785 Erysiphales Species 0.000 claims abstract description 9
- 206010053615 Thermal burn Diseases 0.000 claims abstract description 8
- 241000209504 Poaceae Species 0.000 claims abstract description 4
- 239000000843 powder Substances 0.000 claims description 28
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 14
- 229920001732 Lignosulfonate Polymers 0.000 claims description 13
- 150000008051 alkyl sulfates Chemical class 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- 239000005995 Aluminium silicate Substances 0.000 claims description 11
- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 claims description 11
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 11
- 235000012211 aluminium silicate Nutrition 0.000 claims description 11
- 235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 claims description 11
- 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 11
- 229920002472 Starch Polymers 0.000 claims description 10
- 239000004615 ingredient Substances 0.000 claims description 10
- 239000008107 starch Substances 0.000 claims description 10
- 235000019698 starch Nutrition 0.000 claims description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 claims description 6
- 238000010298 pulverizing process Methods 0.000 claims description 6
- 239000000440 bentonite Substances 0.000 claims description 5
- 229910000278 bentonite Inorganic materials 0.000 claims description 5
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 claims description 5
- 229940051841 polyoxyethylene ether Drugs 0.000 claims description 5
- 229920000056 polyoxyethylene ether Polymers 0.000 claims description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 4
- 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 4
- 229920000142 Sodium polycarboxylate Polymers 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 claims description 4
- 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 claims description 3
- 229920002126 Acrylic acid copolymer Polymers 0.000 claims description 3
- 229920005682 EO-PO block copolymer Polymers 0.000 claims description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- 229920001400 block copolymer Polymers 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 claims description 3
- 229910000388 diammonium phosphate Inorganic materials 0.000 claims description 3
- 235000019838 diammonium phosphate Nutrition 0.000 claims description 3
- SFNALCNOMXIBKG-UHFFFAOYSA-N ethylene glycol monododecyl ether Chemical compound CCCCCCCCCCCCOCCO SFNALCNOMXIBKG-UHFFFAOYSA-N 0.000 claims description 3
- 239000001103 potassium chloride Substances 0.000 claims description 3
- 235000011164 potassium chloride Nutrition 0.000 claims description 3
- 239000000377 silicon dioxide Substances 0.000 claims description 3
- 239000000454 talc Substances 0.000 claims description 3
- 229910052623 talc Inorganic materials 0.000 claims description 3
- 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 claims description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims description 2
- 235000011130 ammonium sulphate Nutrition 0.000 claims description 2
- 229960000892 attapulgite Drugs 0.000 claims description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 2
- 235000013877 carbamide Nutrition 0.000 claims description 2
- 239000004927 clay Substances 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 claims description 2
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 claims description 2
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- 235000019387 fatty acid methyl ester Nutrition 0.000 claims description 2
- 150000004665 fatty acids Chemical class 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- 238000004898 kneading Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 229910000402 monopotassium phosphate Inorganic materials 0.000 claims description 2
- 235000019796 monopotassium phosphate Nutrition 0.000 claims description 2
- 229910052625 palygorskite Inorganic materials 0.000 claims description 2
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 claims description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 2
- 235000011152 sodium sulphate Nutrition 0.000 claims description 2
- 235000019832 sodium triphosphate Nutrition 0.000 claims description 2
- KKDONKAYVYTWGY-UHFFFAOYSA-M sodium;2-(methylamino)ethanesulfonate Chemical compound [Na+].CNCCS([O-])(=O)=O KKDONKAYVYTWGY-UHFFFAOYSA-M 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 5
- 230000002085 persistent effect Effects 0.000 abstract description 5
- 239000008233 hard water Substances 0.000 abstract description 4
- 239000000725 suspension Substances 0.000 abstract description 3
- 239000002671 adjuvant Substances 0.000 abstract description 2
- 239000000575 pesticide Substances 0.000 abstract description 2
- 230000001276 controlling effect Effects 0.000 description 15
- 238000000227 grinding Methods 0.000 description 11
- 241000209219 Hordeum Species 0.000 description 7
- 235000007340 Hordeum vulgare Nutrition 0.000 description 7
- 230000000855 fungicidal effect Effects 0.000 description 7
- 239000000417 fungicide Substances 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- 235000013339 cereals Nutrition 0.000 description 3
- 229930182558 Sterol Natural products 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 230000017858 demethylation Effects 0.000 description 2
- 238000010520 demethylation reaction Methods 0.000 description 2
- 244000052769 pathogen Species 0.000 description 2
- AQIXEPGDORPWBJ-UHFFFAOYSA-N pentan-3-ol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-UHFFFAOYSA-N 0.000 description 2
- 230000003405 preventing effect Effects 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 150000003432 sterols Chemical class 0.000 description 2
- 235000003702 sterols Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- BQPPJGMMIYJVBR-UHFFFAOYSA-N (10S)-3c-Acetoxy-4.4.10r.13c.14t-pentamethyl-17c-((R)-1.5-dimethyl-hexen-(4)-yl)-(5tH)-Delta8-tetradecahydro-1H-cyclopenta[a]phenanthren Natural products CC12CCC(OC(C)=O)C(C)(C)C1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21C BQPPJGMMIYJVBR-UHFFFAOYSA-N 0.000 description 1
- CHGIKSSZNBCNDW-UHFFFAOYSA-N (3beta,5alpha)-4,4-Dimethylcholesta-8,24-dien-3-ol Natural products CC12CCC(O)C(C)(C)C1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21 CHGIKSSZNBCNDW-UHFFFAOYSA-N 0.000 description 1
- XYTLYKGXLMKYMV-UHFFFAOYSA-N 14alpha-methylzymosterol Natural products CC12CCC(O)CC1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21C XYTLYKGXLMKYMV-UHFFFAOYSA-N 0.000 description 1
- FPTJELQXIUUCEY-UHFFFAOYSA-N 3beta-Hydroxy-lanostan Natural products C1CC2C(C)(C)C(O)CCC2(C)C2C1C1(C)CCC(C(C)CCCC(C)C)C1(C)CC2 FPTJELQXIUUCEY-UHFFFAOYSA-N 0.000 description 1
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- BKLIAINBCQPSOV-UHFFFAOYSA-N Gluanol Natural products CC(C)CC=CC(C)C1CCC2(C)C3=C(CCC12C)C4(C)CCC(O)C(C)(C)C4CC3 BKLIAINBCQPSOV-UHFFFAOYSA-N 0.000 description 1
- LOPKHWOTGJIQLC-UHFFFAOYSA-N Lanosterol Natural products CC(CCC=C(C)C)C1CCC2(C)C3=C(CCC12C)C4(C)CCC(C)(O)C(C)(C)C4CC3 LOPKHWOTGJIQLC-UHFFFAOYSA-N 0.000 description 1
- 206010027146 Melanoderma Diseases 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- CAHGCLMLTWQZNJ-UHFFFAOYSA-N Nerifoliol Natural products CC12CCC(O)C(C)(C)C1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21C CAHGCLMLTWQZNJ-UHFFFAOYSA-N 0.000 description 1
- 241000233647 Phytophthora nicotianae var. parasitica Species 0.000 description 1
- 241001123583 Puccinia striiformis Species 0.000 description 1
- 241001515790 Rhynchosporium secalis Species 0.000 description 1
- 241000221662 Sclerotinia Species 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- QBSJHOGDIUQWTH-UHFFFAOYSA-N dihydrolanosterol Natural products CC(C)CCCC(C)C1CCC2(C)C3=C(CCC12C)C4(C)CCC(C)(O)C(C)(C)C4CC3 QBSJHOGDIUQWTH-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- XJLZCPIILZRCPS-ANMPWZFDSA-N eburicol Chemical compound C([C@@]12C)C[C@H](O)C(C)(C)[C@@H]1CCC1=C2CC[C@]2(C)[C@@H]([C@H](C)CCC(=C)C(C)C)CC[C@]21C XJLZCPIILZRCPS-ANMPWZFDSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- CAHGCLMLTWQZNJ-RGEKOYMOSA-N lanosterol Chemical compound C([C@]12C)C[C@@H](O)C(C)(C)[C@H]1CCC1=C2CC[C@]2(C)[C@H]([C@H](CCC=C(C)C)C)CC[C@@]21C CAHGCLMLTWQZNJ-RGEKOYMOSA-N 0.000 description 1
- 229940058690 lanosterol Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- HLPHHOLZSKWDAK-UHFFFAOYSA-M sodium;formaldehyde;naphthalene-1-sulfonate Chemical compound [Na+].O=C.C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HLPHHOLZSKWDAK-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- QPDUQKTYZRXRBC-UHFFFAOYSA-N triazole-4-thione Chemical compound S=C1C=NN=N1 QPDUQKTYZRXRBC-UHFFFAOYSA-N 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
- A01N25/02—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 containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
Landscapes
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Dispersion Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The present invention relates to the technical field of pesticides, particularly to a water dispersible granule of prothioconazole-tebuconazole and preparation method thereof. The water dispersible granule comprises, by weight percentage, prothioconazole, tebuconazole, a dispersing agent, a wetting agent, a chelating agent, a disintegrating agent and a filler. A water dispersible granule comprising prothioconazole and tebuconazole which attains better disintegration and suspension properties in high concentration of hard water is prepared in the present invention by adjusting the type of auxiliaries of the water dispersible granule comprising prothioconazole and tebuconazole, and using proper adjuvant combination. It is particularly suitable for countries and regions of higher water hardness. The water dispersible granule of prothioconazole-tebuconazole of the present invention prolongs the persistent period of the agents, and has a good effect in controlling the crop diseases such as stripe rust, leaf scald and powdery mildew in Gramineae crops, and performs better than the existing water dispersible granule of prothioconazole-tebuconazole.
Description
1001558473 1 2016101530 30 Aug 2016
WATER SOLUBLE GRANULE OF PROTHIOCONAZOLE-TEBUCONAZOLE AND PREPARATION
METHOD THEREOF
Field of the invention
The present invention relates to the technical field of pesticides, and particularly to a water dispersible granule of prothioconazole-tebuconazole and preparation method thereof.
Background of the invention
Currently, the difficulty in controlling plant diseases is increasing: on one hand, the extent and the amount for the occurrence of disease are both raised with the changes in plantation structure and the gradually expanded planting area of cereals and other crops; on the other hand, the resistances of pathogens are increasing year by year under the continuous selection pressure from agents, leading to a significant reduction in single-agent controlling performance. Therefore, the plant disease controlling is confronted with great challenges.
Prothioconazole is a novel broad-spectrum triazolethione systemic fungicide developed by Bayer, its chemical name is 2-(2-( l-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl-l-2-dihydro-3-l,2,3-triazole-3-thione, and its molecular formula is C14H15C12N3OS. The effect mechanism of prothioconazole is to inhibit the demethylation of the precursor of a sterol in fungi, lanosterol or 24-methylenedihydrolanosterol. Through numerous field efficacy tests, the results indicate that prothioconazole not only has good safety and controlling effects, but also increases the production. As compared with the triazole fungicides, prothioconazole has a more broad-spectrum fungicidal activity, and a longer persistent period. It is mainly used for controlling rust disease, powdery mildew, leaf scald, leaf blight, leaf spot, gibberellic disease, etc., in cereal crops such as wheat and barley.
Tebuconazole, the chemical name of which is (RS)-l-(4-chlorophenyl)-4,4-dimethyl-3-(lH-l,2,4-triazol-l-yl-methyl) pentan-3-ol, belongs to the triazole fungicides and is an inhibitor for demethylation of sterol, which is an efficient fungicide used in seed treatment or foliar spray of important economic plants and can 1001558473 2 2016101530 30 Aug 2016 effectively control a variety of rust diseases, powdery mildew, net blotch, root rot, gibberellic disease, smut and seed-bome zonate spot, etc in cereal crops.
Patent publication No. CN104642331 A discloses a fungicidal composition comprising prothioconazole and tebuconazole, and the water dispersible granule thereof. Studies have shown that this fungicidal composition has a higher synergistic effect, and overcomes and delays the resistance of pathogens, with a rapid onset for sterilization, long persistent period, reduced costs for application, and an obviously better controlling performance than the agent used individually, which can be used for controlling the fungal diseases on crops, especially for controlling powdery mildew, sheath blight, fusarium wilt, leaf spot, rust disease, sclerotinia, net blotch, leaf scald, gray mold, black spot, brown spot, black shank and smut, with the performance better than the agent used individually. But it has been found through studies that the preventing effect of the water dispersible granule of prothioconazole-tebuconazole disclosed in this application is unsatisfactory. Therefore, it is required to provide a water dispersible granule of prothioconazole-tebuconazole with better preventing effect.
Summary of the invention
In view of this, the present invention provides a water dispersible granule of prothioconazole-tebuconazole and preparation method thereof. The water dispersible granule of prothioconazole-tebuconazole has a good effect in controlling the crop diseases such as stripe rust, powdery mildew, leaf spot, gibberellic disease, leaf rust and stem rust in the crops such as barley, which performs better than the existing water dispersible granule of prothioconazole-tebuconazole.
To achieve the above purpose of the invention, the present invention provides the following technical solutions:
The present invention provides a water dispersible granule of prothioconazole-tebuconazole, which comprises both prothioconazole and tebuconazole as effective ingredients, as well as a dispersing agent, a wetting agent, a chelating agent, a disintegrating agent and a filler.
As a preference, by weight percentage, it comprises 10%~90% of the effective ingredients, 1%~15% of the dispersing agent, 1%~6.5% of the wetting agent, 1%~5% of the chelating agent, 1%~10% of the disintegrating agent and the balance of the 2016101530 30 Aug 2016 1001558473 3 filler.
Preferably, by weight percentage, it comprises 10%~90% of the effective ingredients, 10%~15% of the dispersing agent, 2.5%~6.5% of the wetting agent, 2%~3% of the chelating agent, 4%~7% of the disintegrating agent and the balance of the filler.
More preferably, by weight percentage, it comprises 10%-90% of the effective ingredients, 10% of the dispersing agent, 3% of the wetting agent, 3% of the chelating agent, 5% of the disintegrating agent and the balance of the filler.
As a preference, the mass ratio of prothioconazole to tebuconazole is (1-90):(1-90).
Preferably, the mass ratio of prothioconazole to tebuconazole is (1-50):(1-50).
Preferably, the mass ratio of prothioconazole to tebuconazole is (1-20):(1-20).
More preferably, the mass ratio of prothioconazole to tebuconazole is 1:1.
As a preference, the weight percentage of the effective ingredients is 20%~80%.
Preferably, the weight percentage of the effective ingredients is 40%~60%.
More preferably, the weight percentage of the effective ingredients is 60%.
As a preference, the dispersing agent is one or a mixture of two or more selected from the group consisting of polyoxyethylene-polyoxypropylene block copolymer, sodium polycarboxylate, lignin sulfonate, sodium alkylnaphthalenesulfonate, sodium alkylnaphthalenesulfonate formaldehyde condensate, alkylphenol polyoxyethylene polyoxypropylene ether, ethylene oxide-propylene oxide block copolymer, maleic acid-acrylic acid copolymer, arylphenol polyoxyethylene ether and alkylphenol sulfonate.
Preferably, the dispersing agent is lignin sulfonate.
In an example provided by the present invention, the lignin sulfonate is REAX910.
As a preference, the wetting agent is one or a mixture of two or more selected from the group consisting of a-sulfo fatty acid methyl ester, alkylsulfate, fatty acid amide N-methyl taurine sodium salt, alkylphenol polyoxyethylene ether sulfate, sodium a-olefin sulfonate, nekal, laureth sulfate, sodium naphthalenesulfonate 1001558473 4 2016101530 30 Aug 2016 formaldehyde condensate and dodecylbenzenesulfonate.
Preferably, the wetting agent is alkylsulfate.
In an example provided by the present invention, the alkylsulfate is WL.
As a preference, the chelating agent is one or a mixture of two or more selected from the group consisting of ethylenediaminetetraacetic acid, disodium ethylenediaminetetraacetate, tetrasodium ethylenediaminetetraacetate and sodium tripolyphosphate.
Preferably, the chelating agent is disodium ethylenediaminetetraacetate.
As a preference, the disintegrating agent is one or a mixture of two or more selected from the group consisting of sodium sulfate, potassium chloride, potassium dihydrogen phosphate, dipotassium hydrogen phosphate, diammonium hydrogen phosphate, urea, ammonium sulfate and com starch.
Preferably, the disintegrating agent is corn starch.
As a preference, the filler is one or a mixture of two or more selected from the group consisting of attapulgite, organic bentonite, light calcium carbonate, talc, anhydrous sodium sulfate, pot clay, diatomite, bentonite, precipitated silica and calcined kaolin.
Preferably, the filler is calcined kaolin.
The present invention further provides a method for preparing the water dispersible granule of prothioconazole-tebuconazole, which comprises: homogeneously mixing the prothioconazole, the tebuconazole, the dispersing agent, the wetting agent, the chelating agent, the disintegrating agent and the filler, pulverizing into fine powders, then kneading and granulating by adding water, drying the obtained granule, to obtain the water dispersible granule.
As a preference, the pulverizing into fine powders is conducted by ultramicro-pulverizing into 600-800 mesh of fine powders.
As a preference, the temperature for drying is 40-65 °C.
The present invention further provides use of the water dispersible granule of prothioconazole-tebuconazole for controlling stripe rust, leaf scald, powdery mildew, leaf spot, gibberellic disease, leaf rust or stem rust in Gramineae crops.
In an example provided by the present invention, the Gramineae crop is barley. 1001558473 5 2016101530 30 Aug 2016
The present invention provides a water dispersible granule of prothioconazole-tebuconazole and preparation method thereof. By weight percentage, the water dispersible granule of prothioconazole-tebuconazole comprises both prothioconazole and a tebuconazole as effective ingredients, as well as a dispersing agent, a wetting agent, a chelating agent, a disintegrating agent and a filler. The beneficial effects of the present invention are: 1. A water dispersible granule comprising prothioconazole and tebuconazole which attains better disintegration and suspension properties in high concentration of hard water is prepared in the present invention by adjusting the type of auxiliaries of the water dispersible granule comprising prothioconazole and tebuconazole, and using proper adjuvant combination. It is particularly suitable for countries and regions of higher water hardness; 2. The water dispersible granule of prothioconazole-tebuconazole of the present invention prolongs the persistent period of the agents, and has a good effect in controlling the crop diseases such as stripe rust, powdery mildew, leaf spot, gibberellic disease, leaf rust and stem rust in crops such as wheat and barley, and performs better than the existing water dispersible granule of prothioconazole-tebuconazole.
Detailed description of the invention
The present invention discloses a water dispersible granule of prothioconazole-tebuconazole and preparation method thereof. Those skilled in the art can use the article content for reference to achieve by appropriately improving the process parameter. It should be particular noted that all the similar substitutions and modifications will be apparent to those skilled in the art, and all of them are considered to be encompassed by the present invention. The methods and use of the present invention have been described through preferred examples, and it is obvious to related personnel that modifications or proper alternations and combinations can be made to the method and use described in the present invention without departing from the content, spirit and scope of the present invention, to achieve and apply of the technology of the present invention.
All the bulk drug or auxiliaries used in the water dispersible granule of prothioconazole-tebuconazole and preparation method thereof provided by the present invention can be commercially available. Wherein, the lignin sulfonate 1001558473 6 2016101530 30 Aug 2016 REAX910 was purchased from MeadWestvaco, and the alkylsulfate WL was purchased from MeadWestvaco.
The present invention will be further illustrated below in conjunction with examples:
Example 1. Water dispersible granule of 60% prothioconazole-tebuconazole 30% of prothioconazole, 30% of tebuconazole, 10% of the dispersing agent lignin sulfonate REAX910 (MeadWestvaco), 3% of the wetting agent alkylsulfate WL (MeadWestvaco), 3% of the chelating agent disodium ethylenediaminetetraacetate, 5% of the disintegrating agent com starch, and the balance of calcined kaolin to 100% were mixed homogeneously, and then ultramicro airlow grinding was conducted to obtain 700 mesh of fine powder. The obtained fine powder was kneaded and granulated by adding water, and dried under 50°C, to obtain the water dispersible granule of 60% prothioconazole-tebuconazole.
Example 2. Water dispersible granule of 72% prothioconazole-tebuconazole 54% of prothioconazole, 18% of tebuconazole, 10% of the dispersing agent lignin sulfonate REAX910 (MeadWestvaco), 3% of the wetting agent alkylsulfate WL (MeadWestvaco), 3% of the chelating agent disodium ethylenediaminetetraacetate, 5% of the disintegrating agent com starch, and the balance of calcined kaolin to 100% were mixed homogeneously, and then ultramicro airlow grinding was conducted to obtain 750 mesh of fine powder. The obtained fine powder was kneaded and granulated by adding water, and dried under 55°C, to obtain the water dispersible granule of 72% prothioconazole-tebuconazole.
Example 3. Water dispersible granule of 40% prothioconazole-tebuconazole 10% of prothioconazole, 30% of tebuconazole, 10% of the dispersing agent lignin sulfonate REAX910 (MeadWestvaco), 3% of the wetting agent alkylsulfate WL (MeadWestvaco), 3% of the chelating agent disodium ethylenediaminetetraacetate, 5% of the disintegrating agent com starch, and the balance of calcined kaolin to 100% were mixed homogeneously, and then ultramicro airlow grinding was conducted to obtain 680 mesh of fine powder. The obtained fine powder was kneaded and 1001558473 7 2016101530 30 Aug 2016 granulated by adding water, and dried under 45°C, to obtain the water dispersible granule of 40% prothioconazole-tebuconazole.
Example 4. Water dispersible granule of 20% prothioconazole-tebuconazole 19% of prothioconazole, 1% of tebuconazole, 10% of the dispersing agent lignin sulfonate REAX910 (MeadWestvaco), 3% of the wetting agent alkylsulfate WL (MeadWestvaco), 3% of the chelating agent disodium ethylenediaminetetraacetate, 5% of the disintegrating agent com starch, and the balance of calcined kaolin to 100% were mixed homogeneously, and then ultramicro airlow grinding was conducted to obtain 680 mesh of fine powder. The obtained fine powder was kneaded and granulated by adding water, and dried under 45°C, to obtain the water dispersible granule of 20% prothioconazole-tebuconazole.
Example 5. Water dispersible granule of 55 % prothioconazole-tebuconazole 1% of prothioconazole, 54% of tebuconazole, 10% of the dispersing agent lignin sulfonate REAX910 (MeadWestvaco), 3% of the wetting agent alkylsulfate WL (MeadWestvaco), 3% of the chelating agent disodium ethylenediaminetetraacetate, 5% of the disintegrating agent com starch, and the balance of calcined kaolin to 100% were mixed homogeneously, and then ultramicro airlow grinding was conducted to obtain 730 mesh of fine powder. The obtained fine powder was kneaded and granulated by adding water, and dried under 40°C, to obtain the water dispersible granule of 55% prothioconazole-tebuconazole.
Example 6. Water dispersible granule of 10% prothioconazole-tebuconazole 7% of prothioconazole, 3% of tebuconazole, 10% of the dispersing agent lignin sulfonate REAX910 (MeadWestvaco), 3% of the wetting agent alkylsulfate WL (MeadWestvaco), 3% of the chelating agent disodium ethylenediaminetetraacetate, 5% of the disintegrating agent com starch, and the balance of calcined kaolin to 100% were mixed homogeneously, and then ultramicro airlow grinding was conducted to obtain 750 mesh of fine powder. The obtained fine powder was kneaded and granulated by adding water, and dried under 60°C, to obtain the water dispersible granule of 10% prothioconazole-tebuconazole. 2016101530 30 Aug 2016 1001558473 8
Example 7. Water dispersible granule of 60% prothioconazole-tebuconazole 30% of prothioconazole, 30% of tebuconazole, the dispersing agent 5% of polyoxyethylene-polyoxypropylene block copolymer, 7% of sodium polycarboxylate, 5% of the wetting agent alkylphenol polyoxyethylene ether sulfate, 2% of the chelating agent ethylenediaminetetraacetic acid, 4% of the disintegrating agent diammonium hydrogen phosphate, 10% of anhydrous sodium sulfate, and the balance of bentonite to 100% were mixed homogeneously, and then ultramicro airlow grinding was conducted to obtain 800 mesh of fine powder. The obtained fine powder was kneaded and granulated by adding water, and dried under 50°C, to obtain the water dispersible granule of 60% prothioconazole-tebuconazole.
Example 8. Water dispersible granule of 40% prothioconazole-tebuconazole 20% of prothioconazole, 20% of tebuconazole, 8% of the dispersing agent maleic acid-acrylic acid copolymer, 7% of sodium polycarboxylate, 2.5% of the wetting agent laureth sulfate, 2.5% of the chelating agent tetrasodium ethylenediaminetetraacetate, 4% of the disintegrating agent potassium chloride, 5% of precipitated silica and the balance of diatomite to 100% were mixed homogeneously, and then ultramicro airlow grinding was conducted to obtain 780 mesh of fine powder. The obtained fine powder was kneaded and granulated by adding water, and dried under 57°C, to obtain the water dispersible granule of 40% prothioconazole-tebuconazole.
Example 9. Water dispersible granule of 70% prothioconazole-tebuconazole 68% of prothioconazole, 2% of tebuconazole, 10% of the dispersing agent lignin sulfonate REAX910 (MeadWestvaco), 3% of the wetting agent alkylsulfate WL (MeadWestvaco), 3% of the chelating agent disodium ethylenediaminetetraacetate, 5% of the disintegrating agent com starch, and the balance of calcined kaolin to 100% were mixed homogeneously, and then ultramicro airlow grinding was conducted to obtain 700 mesh of fine powder. The obtained fine powder was kneaded and granulated by adding water, and dried under 48°C, to obtain the water dispersible granule of 70% prothioconazole-tebuconazole. 1001558473 9 2016101530 30 Aug 2016
Example 10. Water dispersible granule of 75 % prothioconazole-tebuconazole 3% of prothioconazole, 72% of tebuconazole, 10% of the dispersing agent lignin sulfonate REAX910 (MeadWestvaco), 3% of the wetting agent alkylsulfate WL (MeadWestvaco), 3% of the chelating agent disodium ethylenediaminetetraacetate, 5% of the disintegrating agent com starch, and the balance of calcined kaolin to 100% were mixed homogeneously, and then ultramicro airlow grinding was conducted to obtain 760 mesh of fine powder. The obtained fine powder was kneaded and granulated by adding water, and dried under 42°C, to obtain the water dispersible granule of 75% prothioconazole-tebuconazole.
Example 11. Water dispersible granule of 65% prothioconazole-tebuconazole 2% of prothioconazole, 63% of tebuconazole, 8% of the dispersing agent alkylphenol polyoxyethylene polyoxypropylene ether, 5% of ethylene oxide-propylene oxide block copolymer, 6.5% of the wetting agent sodium naphthalene sulfonate formaldehyde condensate, 2.0% of the chelating agent tetrasodium ethylenediaminetetraacetate, 7% of the disintegrating agent urea, and the balance of talc to 100% were mixed homogeneously, and then ultramicro airlow grinding was conducted to obtain 720 mesh of fine powder. The obtained fine powder was kneaded and granulated by adding water, and dried under 50°C, to obtain the water dispersible granule of 65% prothioconazole-tebuconazole.
Example 12. Tests for the main performance indicators
The water dispersible granules obtained in Example 1-11 were subjected to tests for the main performance indicators, and the results are shown in Table 1 below:
Table 1. Tests for indicators of the water dispersible granules obtained by compounding prothioconazole and tebuconazole
Examples Disintegration, s 3 times of D water suspension rate, % Screening (400 mesh) Thermal storage stability 1 40 95.1 99.9 Qualified 2016101530 30 Aug 2016 1001558473 10 2 42 94.2 99.9 Qualified 3 44 94.3 99.9 Qualified 4 48 93.5 99.9 Qualified 5 52 93.1 99.9 Qualified 6 50 94.0 99.9 Qualified 7 58 89.3 99.6 Qualified 8 58 89.5 99.7 Qualified 9 54 92.4 99.9 Qualified 10 54 92.0 99.9 Qualified 11 68 82.8 99.0 Qualified Note: The hardness of 3 times of D water is 1026 mg/L, pH=6.0-7.0, Ca2+:Mg2+=4:l.
It can be known from the test results in Table 1 that, the water dispersible granules of Example 1-11 are capable of achieving better disintegration and suspension properties in high concentration of hard water, which is particularly suitable for countries and regions of higher water hardness.
Example 13. Efficacy test
The efficacy test was conducted in Australia (high concentration of hard water) on the crop of barley, for controlling stripe rust (Puccinia striiformis) and leaf scald (Rhynchosporium secalis). Sprays were applied at the early stage of the diseases in barley and the second application was conducted 14 days later, using prothioconazole, 250 g/L EC (commercially available) and tebuconazole, 430 g/L SC (commercially available) as control agents.
Table 2. Efficacy comparison (21 days after the application)
Dosage for the Controlling efficacy Controlling efficacy Examples application on stripe rust, on leaf scald, g a.i/ha % % 2016101530 30 Aug 2016 1001558473 11 1 126 97.1 97.5 2 126 94.0 94.2 3 126 94.3 94.0 4 126 92.1 92.2 5 126 92.3 92.1 6 126 93.7 93.9 7 126 89.2 89.5 8 126 88.6 88.9 9 126 91.9 92.1 10 126 91.5 92.0 11 126 84.1 84.6 Prothioconazole 250g/L EC 150 80.1 80.4 Tebuconazole 430g/L SC 170 72.8 73.8 Plain water control 0 0 Example 14 of CN104642331 A 140 82.2 82.0 Example 15 of CN 104642331 A 140 82.8 83.0
It can be known from the test results in Table 2 that, the water dispersible granule of prothioconazole-tebuconazole of the present invention has broadened the fungicidal spectrum, increased the fungicidal efficiency, avoided the resistance of the diseases and prolonged the persistent period of the agents, and has good effects for controlling the crop diseases such as stripe rust, leaf scald, powdery mildew, leaf spot, gibberellic disease, leaf rust and stem rust of barley, and performs better than the existing water dispersible granule of prothioconazole-tebuconazole. 2016101530 20 Apr 2017 12
The above described are only the preferred embodiments of the present invention. It should be noted that, for an ordinary skilled in the art, some improvements and modifications can be made to the present invention without departing from the principles of the present invention, and these improvements and modifications should also be deemed to be within the protection scope of the present invention.
Comprises/comprising and grammatical variations thereof when used in this specification are to be taken to specify the presence of stated features, integers, steps or components or groups thereof, but do not preclude the presence or addition of one or more other features, integers, steps, components or groups thereof.
Claims (5)
1. A water dispersible granule of prothioconazole-tebuconazole, comprising both prothioconazole and tebuconazole as effective ingredients, as well as a dispersing agent, a wetting agent, a chelating agent, a disintegrating agent and a filler.
2. The water dispersible granule of prothioconazole-tebuconazole according to claim 1, comprising, by weight percentage, 10%~90% of the effective ingredients, 1%~15% of the dispersing agent, 1%~6.5% of the wetting agent, 1%~5% of the chelating agent, 1%~10% of the disintegrating agent and the balance of the filler; the mass ratio of the prothioconazole to the tebuconazole is (1-90):(1-90).
3. The water dispersible granule of prothioconazole-tebuconazole according to claim 1 or 2, wherein the dispersing agent is one or a mixture of two or more selected from the group consisting of polyoxyethylene-polyoxypropylene block copolymer, sodium polycarboxylate, lignin sulfonate, sodium alkylnapthalenesulfonate, sodium alkylnapthalenesulfonate formaldehyde condensate, alkylphenol polyoxyethylene polyoxypropylene ether, ethylene oxide-propylene oxide block copolymer, maleic acid-acrylic acid copolymer, arylphenol polyoxyethylene ether and alkylphenol sulfonate; the wetting agent is one or a mixture of two or more selected from the group consisting of a-sulfo fatty acid methyl ester, alkylsulfate, fatty acid amide N-methyl taurine sodium salt, alkylphenol polyoxyethylene ether sulfate, sodium a-olefin sulfonate, nekal, laureth sulfate, sodium naphthalenesulfonate formaldehyde condensate, dodecylbenzenesulfonate; the chelating agent is one or a mixture of two or more selected from the group consisting of ethylenediaminetetraacetic acid, disodium ethylenediaminetetraacetate, tetrasodium ethylenediaminetetraacetate and sodium tripolyphosphate; the disintegrating agent is one or a mixture of two or more selected from the group consisting of sodium sulfate, potassium chloride, potassium dihydrogen phosphate, dipotassium hydrogen phosphate, diammonium hydrogen phosphate, urea, ammonium sulfate and com starch; the filler is one or a mixture of two or more selected from the group of attapulgite, organic bentonite, light calcium carbonate, talc, anhydrous sodium sulfate, pot clay, diatomite, bentonite, precipitated silica and calcined kaolin.
4. A method for preparing the water dispersible granule prothioconazole-tebuconazole according to any of claims 1 to 3, comprising: homogeneously mixing the prothioconazole, the tebuconazole, the dispersing agent, the wetting agent, the chelating agent, the disintegrating agent and the filler, pulverizing into fine powders, then kneading and granulating by adding water, drying the obtained granule, to obtain the water dispersible granule; the pulverizing into fine powders is conducted by ultramicro-pulverizing into 600-800 mesh of fine powders; the temperature for drying is 40~65°C.
5. Use of the water dispersible granule of prothioconazole-tebuconazole according to any one of claims 1 to 3 for controlling stripe rust, leaf scald, powdery mildew, leaf spot, gibberellic disease; leaf rust or stem rust in Gramineae crops. SHANDONG WEIFANG RAINBOW CHEMICAL CO., LTD. WATERMARK INTELLECTUAL PROPERTY PTY LTD UIP1533AU00
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