AU2016101699B4 - Water dispersible granule of butroxydim and preparation method thereof - Google Patents
Water dispersible granule of butroxydim and preparation method thereof Download PDFInfo
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- AU2016101699B4 AU2016101699B4 AU2016101699A AU2016101699A AU2016101699B4 AU 2016101699 B4 AU2016101699 B4 AU 2016101699B4 AU 2016101699 A AU2016101699 A AU 2016101699A AU 2016101699 A AU2016101699 A AU 2016101699A AU 2016101699 B4 AU2016101699 B4 AU 2016101699B4
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- butroxydim
- water dispersible
- dispersible granule
- carrier
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- 239000004562 water dispersible granule Substances 0.000 title claims abstract description 66
- 238000002360 preparation method Methods 0.000 title claims abstract description 37
- ZOGDSYNXUXQGHF-XIEYBQDHSA-N Butroxydim Chemical compound CCCC(=O)C1=C(C)C=C(C)C(C2CC(=O)C(\C(CC)=N\OCC)=C(O)C2)=C1C ZOGDSYNXUXQGHF-XIEYBQDHSA-N 0.000 title 1
- ZOGDSYNXUXQGHF-UHFFFAOYSA-N 5-(3-butanoyl-2,4,6-trimethylphenyl)-2-[(Z)-N-ethoxy-C-ethylcarbonimidoyl]-3-hydroxycyclohex-2-en-1-one Chemical compound C(C)ON=C(CC)/C=1C(CC(CC1O)C1=C(C(=C(C=C1C)C)C(CCC)=O)C)=O ZOGDSYNXUXQGHF-UHFFFAOYSA-N 0.000 claims abstract description 74
- 239000002270 dispersing agent Substances 0.000 claims abstract description 61
- 239000000080 wetting agent Substances 0.000 claims abstract description 48
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 46
- 239000002738 chelating agent Substances 0.000 claims abstract description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000011230 binding agent Substances 0.000 claims description 39
- 239000000843 powder Substances 0.000 claims description 31
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 26
- 159000000000 sodium salts Chemical class 0.000 claims description 19
- 239000002994 raw material Substances 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- 229920002472 Starch Polymers 0.000 claims description 12
- 239000000377 silicon dioxide Substances 0.000 claims description 12
- 239000008107 starch Substances 0.000 claims description 12
- 235000019698 starch Nutrition 0.000 claims description 12
- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 claims description 10
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 claims description 10
- 235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 claims description 10
- 229920001732 Lignosulfonate Polymers 0.000 claims description 9
- 239000004117 Lignosulphonate Substances 0.000 claims description 8
- 235000019357 lignosulphonate Nutrition 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 claims description 7
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 claims description 6
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 claims description 6
- 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 5
- 229920002126 Acrylic acid copolymer Polymers 0.000 claims description 5
- 229920005682 EO-PO block copolymer Polymers 0.000 claims description 5
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 claims description 5
- 229910001701 hydrotalcite Inorganic materials 0.000 claims description 5
- 229960001545 hydrotalcite Drugs 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 238000010298 pulverizing process Methods 0.000 claims description 5
- 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 4
- 150000008051 alkyl sulfates Chemical class 0.000 claims description 4
- 239000000440 bentonite Substances 0.000 claims description 4
- 229910000278 bentonite Inorganic materials 0.000 claims description 4
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 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 claims description 4
- 235000019832 sodium triphosphate Nutrition 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
- 239000005995 Aluminium silicate Substances 0.000 claims description 3
- 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 3
- 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
- 239000002202 Polyethylene glycol Substances 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- 235000012211 aluminium silicate Nutrition 0.000 claims description 3
- 239000004927 clay Substances 0.000 claims description 3
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 claims description 3
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 claims description 3
- 229940043264 dodecyl sulfate Drugs 0.000 claims description 3
- 239000008103 glucose Substances 0.000 claims description 3
- 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 3
- 238000004898 kneading Methods 0.000 claims description 3
- 229910052901 montmorillonite Inorganic materials 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims description 3
- 229940051841 polyoxyethylene ether Drugs 0.000 claims description 3
- 229920000056 polyoxyethylene ether Polymers 0.000 claims description 3
- 239000000454 talc Substances 0.000 claims description 3
- 229910052623 talc Inorganic materials 0.000 claims description 3
- 229920001353 Dextrin Polymers 0.000 claims description 2
- 239000004375 Dextrin Substances 0.000 claims description 2
- 235000019425 dextrin Nutrition 0.000 claims description 2
- -1 organobentonite Chemical compound 0.000 claims description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 2
- 229920002261 Corn starch Polymers 0.000 claims 1
- 239000008120 corn starch Substances 0.000 claims 1
- 239000008187 granular material Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000008233 hard water Substances 0.000 abstract description 11
- 239000000575 pesticide Substances 0.000 abstract description 6
- 239000002671 adjuvant Substances 0.000 abstract description 5
- 239000004557 technical material Substances 0.000 description 16
- 239000002245 particle Substances 0.000 description 15
- 239000004480 active ingredient Substances 0.000 description 13
- 230000036515 potency Effects 0.000 description 9
- 229920005551 calcium lignosulfonate Polymers 0.000 description 8
- 239000000725 suspension Substances 0.000 description 7
- 235000007320 Avena fatua Nutrition 0.000 description 5
- 241000209764 Avena fatua Species 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 235000004535 Avena sterilis Nutrition 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 244000100545 Lolium multiflorum Species 0.000 description 2
- 240000006677 Vicia faba Species 0.000 description 2
- 235000010749 Vicia faba Nutrition 0.000 description 2
- 235000002098 Vicia faba var. major Nutrition 0.000 description 2
- 230000004075 alteration Effects 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000007873 sieving Methods 0.000 description 2
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 235000014698 Brassica juncea var multisecta Nutrition 0.000 description 1
- 235000006008 Brassica napus var napus Nutrition 0.000 description 1
- 240000000385 Brassica napus var. napus Species 0.000 description 1
- 235000006618 Brassica rapa subsp oleifera Nutrition 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- 241000209202 Bromus secalinus Species 0.000 description 1
- 235000010523 Cicer arietinum Nutrition 0.000 description 1
- 244000045195 Cicer arietinum Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- 102100028717 Cytosolic 5'-nucleotidase 3A Human genes 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- 241001299819 Hordeum vulgare subsp. spontaneum Species 0.000 description 1
- 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 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 241000033016 Lolium rigidum Species 0.000 description 1
- 241000219745 Lupinus Species 0.000 description 1
- 240000004658 Medicago sativa Species 0.000 description 1
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 1
- 241001668545 Pascopyrum Species 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- 244000046095 Psophocarpus tetragonolobus Species 0.000 description 1
- 235000010580 Psophocarpus tetragonolobus Nutrition 0.000 description 1
- 241000209056 Secale Species 0.000 description 1
- 241000005601 Trisetum Species 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 235000021374 legumes Nutrition 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
- A01N35/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond
-
- 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
Abstract
Abstract The present invention relates to the technical field of pesticides, and discloses a water dispersible granule of butroxydim and preparation method thereof. The water dispersible granule of the present invention comprises butroxydim, a dispersing agent, a wetting agent, a rheological agent, a chelating agent and a carrier. In the present invention, a water dispersible granule of butroxydim which can achieve better disintegrating property and suspending property in high concentration of hard water is prepared by adjusting the type of the auxiliaries in the water dispersible granule of butroxydim and using them in proper combination of adjuvants, and it is particularly suitable for countries and regions having higher water hardness.
Description
WATER DISPERSIBLE GRANULE OF BUTROXYDIM AND 2016101699 29 Aug 2016
PREPARATION METHOD THEREOF
Field of the invention [01] The present invention relates to the technical field of pesticides, and specifically to a water dispersible granule of butroxydim and preparation method thereof.
Background of the invention [02] Butroxydim (chemical name: 5-(3-butyryl-2,4,6-trimethylphenyl)-2-[l-(ethoxyimino)-propyl]-3-hydroxyl-cyclohex-2-en-l-one) is a powdery off-white solid with a melting point of 80.8 °C. It is a postemergence herbicide and is mainly used to control gramineous weeds such as annual rye, wild oat, bromegrass, barley grass, wheat grass, oat grass and the like in the field of legume crops (broad bean, pea, chick pea, fava bean, hyacinth bean, lupin), pasture, alfalfa, flax, rape, cotton, sunflower, soybean, and peanut fields. The dosage is generally 60-180 g/hectare.
[03] A water dispersible granule of pesticide is a dosage form of pesticide which can rapidly disintegrate into original particle size and disperse into a stable suspension in water, and is formed by thoroughly mixing a solid pesticide technical material insoluble in water with a wetting agent, a dispersing agent, other functional auxiliaries and a carrier, pulverizing into fine powdery solid, then kneading, granulating, drying and sieving etc. Water dispersible granule is free of solvents and dusts, safe for the operators, does not drift, avoids the deficiencies of conventional dosage forms such as emulsifiable concentrate, power and wettable powder and the like that are used in a large amount, have many dusts, and so on, but absorbs and utilizes their advantages. It develops quickly, and is considered to be one of the most promising dosage forms in the filed of pesticide processing in the 21st century.
[04] Based on the requirements of dispersing agents in water dispersible granule for technical materials, the technical materials with higher melting point are more favorable for the preparation of the dosage form. However, since the pure butroxydim has a melting point of only 80.8°C, it is difficult to prepare it into water dispersible granules, especially by employing a method of extruding granulation. Moreover, there are problems in conventional water dispersible granules of butroxydim that the products are not shaped well when granulated, and the suspension rate is low when used in countries with high concentration of hard water, such as Australia. 1 [05] Chinese Patent CN105145555A discloses a water dispersible granule of butroxydim and preparation method thereof. It improves the disintegrating and suspending properties of the water dispersible granule of butroxydim by selecting particular dispersing agent, wetting agent, disintegrating agent and solid carrier as adjuvants to prepare the water dispersible granule on the basis of the butroxydim technical material. However, the excellent suspending property of the water dispersible granule of butroxydim mentioned above is only suitable for countries and regions where the water hardness is not high, while in countries commonly having high concentration of hard water, such as Australia, a poor suspending property will still occur when employing the water dispersible granule of butroxydim mentioned above. 2016101699 29 Aug 2016
Summary of the invention [06] In view of this, the object of the present invention is to provide a water dispersible granule of butroxydim and preparation method thereof, such that the water dispersible granule of butroxydim has a better suspension property under conditions of high concentration of hard water.
[07] To achieve the above object, the invention provides the following technical solutions: [08] a water dispersible granule of butroxydim, comprising butroxydim, a dispersing agent, a wetting agent, a rheological agent, a chelating agent and a carrier.
[09] In response to the defect that the existing water dispersible granules of butroxydim are not suitable for high concentration of hard water, the type of adjuvants is adjusted in the present invention, using a rheological agent and a chelating agent instead of the original disintegrating agent, and meanwhile the specific raw material of each component is used in combination to prepare a water dispersible granule of butroxydim, thereby compensating for the defect in the prior art.
[10] Preferably, the water dispersible granule of the present invention comprises, by weight, 10%-80% of butroxydim, 2%-15% of a dispersing agent, l%-6% of a wetting agent, l%-5% of a rheological agent, l%-5% of a chelating agent and the balance of a carrier; further preferably, comprises 10%-80% of butroxydim, 5%-12% of a dispersing agent, 2%-4% of a wetting agent, 3%-5% of a rheological agent, l%-3% of a chelating agent and the balance of a carrier; and more preferably, comprises 10%-80% of butroxydim, 10% of a dispersing agent, 3% of a wetting agent, 5% of a rheological agent, 3% of a chelating agent and the balance of a carrier, wherein the butroxydim preferably can be 20%-70% by weight, further preferably 40%-60%, and 2 most preferably 50%. 2016101699 29 Aug 2016 [11] Preferably, the dispersing agent is one or more selected from the group consisting of polycarboxylic acid sodium salt, lignosulphonate, alkylnaphthalenesulfonic acid sodium salt, alkylnaphthalenesulfonic acid formaldehyde condensate sodium salt, alkylphenol polyoxyethylene polyoxypropylene ether, ethylene oxide-propylene oxide block copolymer, maleic acid-acrylic acid copolymer; more preferably two of polycarboxylic acid sodium salt, lignosulphonate, alkylnaphthalenesulfonic acid sodium salt, alkylnaphthalenesulfonic acid formaldehyde condensate sodium salt, alkylphenol polyoxyethylene polyoxypropylene ether, ethylene oxide-propylene oxide block copolymer, and maleic acid-acrylic acid copolymer, wherein the weight ratio between the dispersing agents is 1:1. Wherein, the polycarboxylic acid sodium salt is preferably one or both of SC/213 and TERSPERSE 2700.
[12] In some specific embodiments of the present invention, the dispersing agent is both SC/213 and TERSPERSE 2700, both SC/213 and lignosulphonate, both ethylene oxide-propylene oxide block copolymer and alkylnaphthalenesulfonic acid sodium salt, both alkylphenol polyoxyethylene polyoxypropylene ether and alkylnaphthalenesulfonic acid sodium salt, both lignosulphonate and alkylnaphthalenesulfonic acid formaldehyde condensate sodium salt, or both alkylphenol polyoxyethylene polyoxypropylene ether and maleic acid-acrylic acid copolymer.
[13] Preferably, the wetting agent is one or more selected from the group consisting of alkyl sulfate, alkylphenol polyoxyethylene ether sulfate, Nekal, lauryl sulfate, naphthalene sulfonic acid formaldehyde condensate sodium salt and dodecyl benzenesulfonate. Wherein, the alkyl sulfate is preferably TERWET 1004. In some specific embodiments of the present invention, the wetting agent can be selected as a combination of naphthalene sulfonic acid formaldehyde condensate sodium salt and dodecyl benzenesulfonate, or a combination of dodecyl benzenesulfonate and Nekal.
[14] Preferably, the rheological agent is one or more selected from the group consisting of precipitated silica, organobentonite, montmorillonite and hydrotalcite.
[15] Preferably, the chelating agent is one or more selected from the group consisting of ethylenediaminetetraacetic acid, disodium ethylenediaminetetraacetate, tetrasodium ethylenediaminetetraacetate and sodium tripolyphosphate.
[16] Preferably, the carrier is one or more selected from the group consisting of pottery clay, kaolin, diatomite, bentonite, precipitated silica, com starch and talc. 3 [17] In addition, the water dispersible granule of the present invention further comprises a binding agent. The binding agent is 1%-10% by weight, more preferably l%-5%. 2016101699 29 Aug 2016 [18] Preferably, the binding agent is one or more selected from the group consisting of polyvinylpyrrolidone, polyethylene glycol, lignosulphonate, glucose, soluble starch and dextrin.
[19] In some specific embodiments of the present invention, the percentage by weight of each component can be selected as follows: (1) 50.5% of butroxydim, 10% of the dispersing agent, 3% of the wetting agent, 3% of chelating agent, 5% of the rheological agent, 5% of the binding agent, and 23.5% of the carrier; (2) 50.5% of butroxydim, 10% of the dispersing agent, 3% of the wetting agent, 3% of the chelating agent, 5% of the rheological agent, and 28.5% of the carrier; (3) 10.2% of butroxydim, 10% of the dispersing agent, 3% of the wetting agent, 3% of chelating agent, 5% of the rheological agent, 5% of the binding agent, and 63.8% of the carrier; (4) 81.7% of butroxydim, 4.5% of the dispersing agent, 1.5% of the wetting agent, 3.5% of the chelating agent, 2% of the rheological agent, 5.5% of the binding agent, and 1.3% of the carrier; (5) 50.5% of butroxydim, 7% of the dispersing agent, 5% of the wetting agent, 3.5% of the chelating agent, 5.5% of the rheological agent, 8% of the binding agent, and 20.5% of the carrier. (6) 30.7% of butroxydim, 10% of the dispersing agent, 6% of the wetting agent, 1.5% of the chelating agent, 3.5% of the rheological agent, 3% of the binding agent, and 45.3% of the carrier. (7) 61.3% of butroxydim, 14% of the dispersing agent, 6% of the wetting agent, 2.5% of the chelating agent, 2.0% of the rheological agent, 6% of the binding agent, and 8.2% of the carrier.
[20] Meanwhile, the present invention further provides a method for preparing the water dispersible granule of butroxydim: uniformly mixing the butroxydim, a dispersing agent, a wetting agent, a rheological agent, a chelating agent and a carrier, and pulverizing into fine powders, then kneading and granulating after adding water, and drying the resultant particles to obtain the water dispersible granule. 4 [21] Wherein, the pulverizing into fine powders is preferably ultrafinely pulverizing into fine powders of 500-800 mesh. The drying is preferably performed at 40-60 °C. Preferably, the preparing process further comprises adding a binding agent into the raw materials and uniformly mixing together. 2016101699 29 Aug 2016 [22] The disintegrating property and suspending property in high concentration of hard water of the water dispersible granule of butroxydim of the present invention and the products of Examples 1-6 in the prior patent CN105145555A are compared, and the results show that they are significantly higher for the water dispersible granule of the present invention than for the products in the prior patent.
[23] As is known from the above technical solutions, a water dispersible granule of butroxydim which can achieve better disintegrating property and suspending property in high concentration of hard water is prepared in the present invention by adjusting the type of auxiliaries thereof and using them in a proper adjuvant combination, and which is particularly suitable for countries and regions having higher water hardness.
Detailed embodiments [24] The examples of the present invention discloses a water dispersible granule of butroxydim and preparation method thereof, which can be achieved by those skilled in the art through learning from the disclosure herein and making a proper improvement for the process parameters. It is particularly to be noted that all the similar substitutions and alterations are apparent for those skilled in the art, and are considered to be encompassed within the present invention. The water dispersible granule of the present invention and the preparation method thereof have been described by way of preferred embodiments, and it is apparent that the related personnel would achieve and apply the techniques of the present invention by alterations or proper modifications and combinations of the methods and applications described herein, without departing from the content, spirit and scope of the preset invention.
[25] In the water dispersible granule of butroxydim of the present invention, butroxydim is based on the butroxydim technical material (with a content ^98%), and other auxiliary adjuvants are all commercially available, for example, SC/213 is purchased from Solvay Auxiliary Cooperation, TERSPERSE 2700 is purchased from Huntsman Auxiliary Cooperation, and TERWET 1004 is purchased form Huntsman Auxiliary Cooperation.
[26] One type of the water dispersible granule of butroxydim and the preparation method thereof provided by the present invention is further described below. 5
Example 1: Preparation of the water dispersible granule of the present invention 2016101699 29 Aug 2016 1. Raw materials
Butroxydim technical material (with a content ^98%, the active ingredient) 505 g (50.5%) SC/213 (dispersing agent) 50 g (5%) TERSPERSE 2700 (dispersing agent) 50 g (5%) TERWET 1004 (wetting agent) 30 g (3%) Disodium EDTA (chelating agent) 30 g (3%) Precipitated silica (rheological agent) 50 g (5%) Calcium lignosulphonate (binding agent) 50 g (5%) Com starch (carrier) 235 g (23.5%) In total 1000 g 2. Preparation method [27] The butroxydim, dispersing agent, wetting agent, binding agent, rheological agent, chelating agent and carrier were mixed uniformly and ultrafinely pulverized into fine powders of 500-800 mesh. Then, the fine powders were kneaded and granulated after water was added. The resultant particles were dried at 40°C-60°C to obtain the water dispersible granule.
Example 2: Preparation of the water dispersible granule of the present invention 1. Raw materials
Butroxydim technical material (with a content -5=98%, the active ingredient) 505 g (50.5%) SC/213 (dispersing agent) 50 g (5%) TERSPERSE 2700 (dispersing agent) 50 g (5%) TERWET 1004 (wetting agent) 30 g (3%) Disodium EDTA (chelating agent) 30 g (3%) Precipitated silica (rheological agent) 50 g (5%) 6
Com starch (carrier) 285 g (28.5%) In total 1000 g 2. Preparation method 2016101699 29 Aug 2016 [28] The butroxydim, dispersing agent, wetting agent, binding agent, rheological agent, chelating agent and carrier were mixed uniformly and ultrafinely pulverized into fine powders of 500-800 mesh. Then, the fine powders were kneaded and granulated after water was added. The resultant particles were dried at 40°C-60°C to obtain the water dispersible granule.
Example 3: Preparation of the water dispersible granule of the present invention 1. Raw materials
Butroxydim technical material (with a content ^98%, the active ingredient) 505 g (50.5%) SC/213 (dispersing agent) 50 g (5%) TERSPERSE 2700 (dispersing agent) 50 g (5%) TERWET 1004 (wetting agent) 30 g (3%) EDTA (chelating agent) 30 g (3%) Precipitated silica (rheological agent) 50 g (5%) Calcium lignosulphonate (binding agent) 50 g (5%) Com starch (carrier) 235 g (23.5%) In total 1000 g 2. Preparation method [29] The butroxydim, dispersing agent, wetting agent, binding agent, rheological agent, chelating agent and carrier were mixed uniformly and ultrafinely pulverized into fine powders of 500-800 mesh. Then, the fine powders were kneaded and granulated after water was added. The resultant particles were dried at 40°C-60°C to obtain the water dispersible granule. 7 2016101699 29 Aug 2016
Example 4: Preparation of the water dispersible granule of the present invention 1. Raw materials
Butroxydim technical material (with a content -5=98%. the active ingredient) 505 g (50.5%) SC/213 (dispersing agent) 50 g (5%) Lignosulphonate (dispersing agent) 50 g (5%) TERWET 1004 (wetting agent) 30 g (3%) Disodium EDTA (chelating agent) 30 g (3%) Precipitated silica (rheological agent) 50 g (5%) Calcium lignosulphonate (binding agent) 50 g (5%) Com starch (carrier) 235 g (23.5%) In total 1000 g 2. Preparation method [30] The butroxydim, dispersing agent, wetting agent, binding agent, rheological agent, chelating agent and carrier were mixed uniformly and ultrafinely pulverized into fine powders of 500-800 mesh. Then, the fine powders were kneaded and granulated after water was added. The resultant particles were dried at 40°C-60°C to obtain the water dispersible granule.
Example 5: Preparation of the water dispersible granule of the present invention 1. Raw materials
Butroxydim technical material (with a content -598%, the active ingredient) 505 g (50.5%) SC/213 (dispersing agent) 50 g (5%) TERSPERSE 2700 (dispersing agent) 50 g (5%) Alkylphenol polyoxyethylene ether sulfate (wetting agent) 30 g (3%) Disodium EDTA (chelating agent) 30 g (3%) 8
Precipitated silica (rheological agent) 50 g (5%) Calcium lignosulphonate (binding agent) 50 g (5%) Com starch (carrier) 235 g (23.5%) In total 1000 g 2. Preparation method 2016101699 29 Aug 2016 [31] The butroxydim, dispersing agent, wetting agent, binding agent, rheological agent, chelating agent and carrier were mixed uniformly and ultrafinely pulverized into fine powders of 500-800 mesh. Then, the fine powders were kneaded and granulated after water was added. The resultant particles were dried at 40°C-60°C to obtain the water dispersible granule.
Example 6: Preparation of the water dispersible granule of the present invention 1. Raw materials
Butroxydim technical material (with a content )5 98%, the active ingredient) 505 g (50.5%) SC/213 (dispersing agent) 50 g (5%) TERSPERSE 2700 (dispersing agent) 50 g (5%) TERWET 1004 (wetting agent) 30 g (3%) Disodium EDTA (chelating agent) 30 g (3%) Hydrotalcite (rheological agent) 50 g (5%) Calcium lignosulphonate (binding agent) 50 g (5%) Com starch (carrier) 235 g (23.5%) In total 1000 g 2. Preparation method [32] The butroxydim, dispersing agent, wetting agent, binding agent, rheological agent, chelating agent and carrier were mixed uniformly and ultrafinely pulverized into fine powders of 500-800 mesh. Then, the fine powders were kneaded and 9 granulated after water was added. The resultant particles were dried at 40°C-60°C to obtain the water dispersible granule. 2016101699 29 Aug 2016
Example 7: Preparation of the water dispersible granule of the present invention 1. Raw materials
Butroxydim technical material (with a content -5=98%, the active ingredient) 505 g (50.5%) SC/213 (dispersing agent) 50 g (5%) TERSPERSE 2700 (dispersing agent) 50 g (5%) TERWET 1004 (wetting agent) 30 g (3%) Disodium EDTA (chelating agent) 30 g (3%) Precipitated silica (rheological agent) 50 g (5%) Calcium lignosulphonate (binding agent) 50 g (5%) Kaolin (carrier) 235 g (23.5%) In total 1000 g 2. Preparation method [33] The butroxydim, dispersing agent, wetting agent, binding agent, rheological agent, chelating agent and carrier were mixed uniformly and ultrafinely pulverized into fine powders of 500-800 mesh. Then, the fine powders were kneaded and granulated after water was added. The resultant particles were dried at 40°C-60°C to obtain the water dispersible granule.
Example 8: Preparation of the water dispersible granule of the present invention 1. Raw materials
Butroxydim technical material (with a content ^98%, the active ingredient) 505 g (50.5%) Ethylene oxide-propylene oxide block copolymer (dispersing agent) 50 g (5%) Alkylnaphthalenesulfonic acid sodium 50 g (5%) 10 salt (dispersing agent) Alkyl sulfate (wetting agent) 30 g (3%) Tetrasodium EDTA (chelating agent) 30 g (3%) Organobentonite (rheological agent) 50 g (5%) Polyethylene glycol (binding agent) 50 g (5%) Bentonite (carrier) 235 g (23.5%) In total 1000 g 2. Preparation method 2016101699 29 Aug 2016 [34] The butroxydim, dispersing agent, wetting agent, binding agent, rheological agent, chelating agent and carrier were mixed uniformly and ultrafinely pulverized into fine powders of 500-800 mesh. Then, the fine powders were kneaded and granulated after water was added. The resultant particles were dried at 40°C-60°C to obtain the water dispersible granule.
Example 9: Preparation of the water dispersible granule of the present invention 1. Raw materials
Butroxydim technical material (with a content ^98%, the active ingredient) 102 g (10.2%) SC/213 (dispersing agent) 50 g (5%) TERSPERSE 2700 (dispersing agent) 50 g (5%) TERWET 1004 (wetting agent) 30 g (3%) Disodium EDTA (chelating agent) 30 g (3%) Precipitated silica (rheological agent) 50 g (5%) Calcium lignosulphonate (binding agent) 50 g (5%) Com starch (carrier) 638 g (63.8%) In total 1000 g 11 2. Preparation method 2016101699 29 Aug 2016 [35] The butroxydim, dispersing agent, wetting agent, binding agent, rheological agent, chelating agent and carrier were mixed uniformly and ultrafinely pulverized into fine powders of 500-800 mesh. Then, the fine powders were kneaded and granulated after water was added. The resultant particles were dried at 40°C-60°C to obtain the water dispersible granule.
Example 10: Preparation of the water dispersible granule of the present invention 1. Raw materials
Butroxydim technical material (with a content ^ 98%, the active ingredient) 817 g (81.7%) Alkylphenol polyoxyethylene polyoxypropylene ether (dispersing agent) 40 g (4%) Maleic acid-acrylic acid copolymer (dispersing agent) 5 g (0.5%) Lauryl sulfate (wetting agent) 15 g (1.5%) Sodium tripolyphosphate (chelating agent) 35 g (3.5%) Montmorillonite (rheological agent) 20 g (2%) Cyclodextrin (binding agent) 55 g (5.5%) Talc (carrier) 13 g (1.3%) In total 1000 g 2. Preparation method [36] The butroxydim, dispersing agent, wetting agent, binding agent, rheological agent, chelating agent and carrier were mixed uniformly and ultrafinely pulverized into fine powders of 500-800 mesh. Then, the fine powders were kneaded and granulated after water was added. The resultant particles were dried at 40°C-60°C to obtain the water dispersible granule. 12
Example 11: Preparation of the water dispersible granule of the present invention 1. Raw materials
Butroxydim technical material (with a content -5=98%. the active ingredient) 505 g (50.5%) SC/213 (dispersing agent) 30 g (3%) TERSPERSE 2700 (dispersing agent) 40 g (4%) TERWET 1004 (wetting agent) 50 g (5%) Disodium EDTA (chelating agent) 35 g (3.5%) Precipitated silica (rheological agent) 55 g (5.5%) Calcium lignosulphonate (binding agent) 80 g (8%) Com starch (carrier) 205 g (20.5%) In total 1000 g 2016101699 29 Aug 2016 2. Preparation method [37] The butroxydim, dispersing agent, wetting agent, binding agent, rheological agent, chelating agent and carrier were mixed uniformly and ultrafinely pulverized into fine powders of 500-800 mesh. Then, the fine powders were kneaded and granulated after water was added. The resultant particles were dried at 40°C-60°C to obtain the water dispersible granule.
Example 12: Preparation of the water dispersible granule of the present invention 1. Raw materials
Butroxydim technical material (with a content -5=98%. the active ingredient) 307 g (30.7%) Lignosulfonate (dispersing agent) 60 g (6%) Alkylnaphthalenesulfonic acid formaldehyde condensate sodium salt (dispersing agent) 40 g (4%) Nekal (wetting agent) 10g(l%) 13
Dodecyl benzenesulfonate (wetting agent) 50 g (5%) Tetrasodium EDTA (chelating agent) 15 g (1.5%) Hydrotalcite (rheological agent) 35 g (3.5%) Glucose (binding agent) 30 g (3%) Pottery clay (carrier) 453 g (45.3%) In total 1000 g 2. Preparation method 2016101699 29 Aug 2016 [38] The butroxydim, dispersing agent, wetting agent, binding agent, rheological agent, chelating agent and carrier were mixed uniformly and ultrafinely pulverized into fine powders of 500-800 mesh. Then, the fine powders were kneaded and granulated after water was added. The resultant particles were dried at 40°C-60°C to obtain the water dispersible granule.
Example 13: Preparation of the water dispersible granule of the present invention 1. Raw materials
Butroxydim technical material (with a content (598% . the active ingredient) 613 g (61.3%) Alkylphenol polyoxyethylene polyoxypropylene ether (dispersing agent) 20 g (2%) Alkylnaphthalenesulfonic acid sodium salt (dispersing agent) 120 g (12%) Naphthalene sulfonic acid formaldehyde condensate sodium salt (wetting agent) 15 g (1.5%) Dodecyl benzenesulfonate (wetting agent) 45 g (4.5%) Sodium tripolyphosphate (chelating agent) 25 g (2.5%) 14
Hydrotalcite (rheological agent) 20 g (2.0%) Soluble starch (binding agent) 60 g (6%) Bentonite (carrier) 82 g (8.2%) In total lOOOg 2. Preparation method 2016101699 29 Aug 2016 [39] The butroxydim, dispersing agent, wetting agent, binding agent, rheological agent, chelating agent and carrier were mixed uniformly and ultrafinely pulverized into fine powders of 500-800 mesh. Then, the fine powders were kneaded and granulated after water was added. The resultant particles were dried at 40°C-60°C to obtain the water dispersible granule.
Example 14: Comparative test [40] Using the products of Examples 1-6 in the prior patent CN105145555A as controls (hereinafter abbreviated as CN1-CN6), the performance index of the products of all examples of the present invention and the controls was detected in hard water of the same high concentration. The results are shown in Table 1.
Table 1. Comparison with the performance index of Examples in the Patent CN105145555A
Examples Disintegrating property, s Suspension rate in 3-times D water, % Sieving (400 mesh) Thermal storage stability 1 40 98.2 99.9 Qualified 2 48 98.0 99.9 Qualified 3 42 91.6 99.9 Qualified 4 44 85.5 99.8 Qualified 5 62 86.3 99.6 Qualified 6 50 94.6 99.8 Qualified 7 58 92.2 99.0 Qualified 8 68 84.2 99.4 Qualified 9 56 89.0 99.9 Qualified 15 10 72 81.4 99.3 Qualified 11 66 85.0 99.5 Qualified 12 74 82.2 99.1 Qualified 13 74 82.7 99.0 Qualified CN1 40 78.9 99.0 Qualified CN 2 50 77.8 98.5 Qualified CN 3 50 80.1 99.0 Qualified CN 4 46 78.0 99.0 Qualified CN 5 40 76.5 99.0 Qualified CN 6 50 77.1 99.0 Qualified
Note: The hardness of 3-times D water is 1026 mg/L, pH=6.0-7.0, Ca2+:Mg2+=4:l.
[41] As can be seen from Table 1, the water dispersible granules of butroxydim of the present invention still can achieve a better level of suspension rate in a higher 3-times D water hardness, the highest of which can be up to 98.2%. However, the suspension rate of the products in the prior patent is only up to 80%, which is obviously not as good as that of the present invention. 2016101699 29 Aug 2016
Example 13: Potency test [42] The potency of the products of Examples 1-13 in the present invention was tested on the crop CANOLA against annual ryegrass (Lolium rigidum) and wild oat (Avena fatua) in Australia (high concentration of hard water), wherein the dosage was 40 g a.i/ha and the product of Example 1 in CN105145555A was used as the control group. The results are shown in Table 2.
Table 2. Comparison of potency (27 d after dosing)
Examples Controlling potency against annual ryegrass, % Controlling potency against wild oat, % 1 95.0 95.0 2 94.5 94.3 3 92.8 92.2 4 86.0 86.2 5 86.5 86.3 6 92.2 92.0 7 91.7 91.5 16 8 85.1 85.5 9 87.8 87.0 10 81.8 81.3 11 83.5 84.0 12 82.1 82.0 13 82.5 83.0 CN1 76.8 78.1 Clean water control 0 0 [43] As can be seen from Table 2, the water dispersible granules of butroxydim of the present invention as a whole exhibit a better controlling potency in the potency test conducted in Australia, where the hard water has a high concentration. Different controlling potencies are also shown in terms of different formulae and dosages, highest of which can be up to 95%. However, the products of Examples 1-6 in the prior patent CN105145555A all display a poor suspension rate in high concentration of hard water, and the controling potency thereof is also affected, and thus is not as good as that of the present invention. 2016101699 29 Aug 2016 [44] The above description is merely for understanding the method of the present invention and the core concept thereof. It should be noted that, those ordinary skilled in the art can make various improvements and modifications to the present invention without departing from the principle of the present invention, and these improvements and modifications also fall into the protection scope of the claims of the present invention. 17
Claims (5)
1. A water dispersible granule of butroxydim, wherein it comprises, by weight, 10%-80% of butroxydim, 2%-15% of a dispersing agent, l%-6% of a wetting agent, l%-5% of a rheological agent, l%-5% of a chelating agent and the balance of a carrier; the dispersing agent is one or more selected from the group consisting of polycarboxylic acid sodium salt, lignosulphonate, alkylnaphthalenesulfonic acid sodium salt, alkylnaphthalenesulfonic acid formaldehyde condensate sodium salt, alkylphenol polyoxyethylene polyoxypropylene ether, ethylene oxide-propylene oxide block copolymer and maleic acid-acrylic acid copolymer; the wetting agent is one or more selected from the group consisting of alkyl sulfate, alkylphenol polyoxyethylene ether sulfate, Nekal, lauryl sulfate, naphthalene sulfonic acid formaldehyde condensate sodium salt and dodecyl benzenesulfonate; the rheological agent is one or more selected from the group consisting of precipitated silica, organobentonite, montmorillonite and hydrotalcite; the chelating agent is one or more selected from the group consisting of ethylenediaminetetraacetic acid, disodium ethylenediaminetetraacetate, tetrasodium ethylenediaminetetraacetate and sodium tripolyphosphate; the carrier is one or more selected from the group consisting of pottery clay, kaolin, diatomite, bentonite, precipitated silica, corn starch and talc.
2. The water dispersible granule of butroxydim according to claim 1, wherein it further comprises a binder, and the binder is 1%-10% by weight.
3. The water dispersible granule of butroxydim according to claim 2, wherein the binder is one or more selected from the group consisting of polyvinylpyrrolidone, polyethylene glycol, lignosulphonate, glucose, soluble starch and dextrin.
4. A method for preparing the water dispersible granule of butroxydim of claim 1, comprising uniformly mixing butroxydim, the dispersing agent, the wetting agent, the rheological agent, the chelating agent and the carrier as raw materials and pulverizing the mixture into fine powders, then kneading and granulating the fine powders after adding water, and drying the resultant granule to obtain the water dispersible granule.
5. The preparation method according to claim 4, wherein in the mixing, the raw materials further comprise a binder.
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| AU2018101558B4 (en) * | 2018-10-18 | 2019-05-16 | Yi Xiang Zhang | Synthetic method for a butroxydim water dispersible granule |
| AU2018250461B1 (en) * | 2018-10-18 | 2019-12-12 | Yi Xiang Zhang | Synthetic method for a butroxydim water dispersible granule |
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| CN111789114A (en) * | 2020-07-19 | 2020-10-20 | 江苏云帆化工有限公司 | Butylbenzene-clomazone dry suspending agent and preparation method thereof |
| CN114642208B (en) * | 2020-12-21 | 2023-07-21 | 山东潍坊润丰化工股份有限公司 | Fluazinam water dispersible granule and preparation method thereof |
| CN114982751B (en) * | 2022-07-01 | 2023-10-03 | 河北双吉化工有限公司 | Production process of pesticide water dispersible granule with good stability |
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| CN101263808A (en) * | 2008-04-17 | 2008-09-17 | 深圳市朗钛生物科技有限公司 | Diflubenzuron water dispersion granule and preparation thereof |
| CN103975917A (en) * | 2014-05-13 | 2014-08-13 | 山东潍坊润丰化工股份有限公司 | Propanil Wwater dispersible granules |
| CN105123731B (en) * | 2015-09-24 | 2018-05-25 | 山东潍坊润丰化工股份有限公司 | A kind of thifensulfuronmethyl and the water dispersible granules of clodinafop-propargyl and its preparation method and application |
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| AU2018101558B4 (en) * | 2018-10-18 | 2019-05-16 | Yi Xiang Zhang | Synthetic method for a butroxydim water dispersible granule |
| AU2018250461B1 (en) * | 2018-10-18 | 2019-12-12 | Yi Xiang Zhang | Synthetic method for a butroxydim water dispersible granule |
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