CN117562066B - Wettable powder containing flumioxazin and glufosinate-ammonium, preparation method and application thereof - Google Patents
Wettable powder containing flumioxazin and glufosinate-ammonium, preparation method and application thereof Download PDFInfo
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- CN117562066B CN117562066B CN202410067361.1A CN202410067361A CN117562066B CN 117562066 B CN117562066 B CN 117562066B CN 202410067361 A CN202410067361 A CN 202410067361A CN 117562066 B CN117562066 B CN 117562066B
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- CN
- China
- Prior art keywords
- glufosinate
- flumioxazin
- wettable powder
- agent
- ammonium
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 title claims abstract description 79
- 238000002360 preparation method Methods 0.000 title claims abstract description 60
- FOUWCSDKDDHKQP-UHFFFAOYSA-N flumioxazin Chemical compound FC1=CC=2OCC(=O)N(CC#C)C=2C=C1N(C1=O)C(=O)C2=C1CCCC2 FOUWCSDKDDHKQP-UHFFFAOYSA-N 0.000 title claims abstract description 56
- 239000004563 wettable powder Substances 0.000 title claims abstract description 49
- 239000002270 dispersing agent Substances 0.000 claims abstract description 86
- 239000000080 wetting agent Substances 0.000 claims abstract description 60
- 239000005561 Glufosinate Substances 0.000 claims abstract description 59
- 239000008139 complexing agent Substances 0.000 claims abstract description 39
- 239000002994 raw material Substances 0.000 claims abstract description 38
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims abstract description 34
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 31
- 239000000194 fatty acid Substances 0.000 claims abstract description 31
- 229930195729 fatty acid Natural products 0.000 claims abstract description 31
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 31
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims abstract description 17
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims abstract description 17
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims abstract description 17
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical group OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000005642 Oleic acid Substances 0.000 claims abstract description 17
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims abstract description 17
- 235000021314 Palmitic acid Nutrition 0.000 claims abstract description 17
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims abstract description 17
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims abstract description 17
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims abstract description 17
- YWYZEGXAUVWDED-UHFFFAOYSA-N triammonium citrate Chemical compound [NH4+].[NH4+].[NH4+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O YWYZEGXAUVWDED-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000000945 filler Substances 0.000 claims abstract description 14
- 238000002156 mixing Methods 0.000 claims description 37
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical group C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 claims description 27
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 25
- 229940074404 sodium succinate Drugs 0.000 claims description 24
- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 claims description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 12
- 238000010902 jet-milling Methods 0.000 claims description 12
- 239000006229 carbon black Substances 0.000 claims description 11
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 claims description 11
- 238000003756 stirring Methods 0.000 claims description 7
- 238000009333 weeding Methods 0.000 claims description 6
- 235000013339 cereals Nutrition 0.000 claims description 3
- WVRXNIBQZAKZTE-UHFFFAOYSA-N 1-methylidene-2h-naphthalene Chemical compound C1=CC=C2C(=C)CC=CC2=C1 WVRXNIBQZAKZTE-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 15
- 230000002363 herbicidal effect Effects 0.000 abstract description 10
- 239000004009 herbicide Substances 0.000 abstract description 8
- 238000003860 storage Methods 0.000 abstract description 3
- 239000004480 active ingredient Substances 0.000 abstract description 2
- OMKBBIQIHSBGRL-UHFFFAOYSA-N 1-methylidene-2h-naphthalene;sodium Chemical compound [Na].C1=CC=C2C(=C)CC=CC2=C1 OMKBBIQIHSBGRL-UHFFFAOYSA-N 0.000 description 24
- 241000196324 Embryophyta Species 0.000 description 22
- 239000000126 substance Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 238000012360 testing method Methods 0.000 description 17
- 230000000694 effects Effects 0.000 description 14
- 229940079593 drug Drugs 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 5
- 150000004671 saturated fatty acids Chemical class 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 238000009736 wetting Methods 0.000 description 5
- 239000002738 chelating agent Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000000575 pesticide Substances 0.000 description 4
- 241000209504 Poaceae Species 0.000 description 3
- 230000000857 drug effect Effects 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 3
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000001647 drug administration Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000005338 heat storage Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000000691 measurement method Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920000056 polyoxyethylene ether Polymers 0.000 description 2
- 229940051841 polyoxyethylene ether Drugs 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 241001290610 Abildgaardia Species 0.000 description 1
- 229910002016 Aerosil® 200 Inorganic materials 0.000 description 1
- 240000001579 Cirsium arvense Species 0.000 description 1
- 235000005918 Cirsium arvense Nutrition 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 206010059866 Drug resistance Diseases 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
- 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
- STECJAGHUSJQJN-USLFZFAMSA-N LSM-4015 Chemical compound C1([C@@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-USLFZFAMSA-N 0.000 description 1
- 229940087098 Oxidase inhibitor Drugs 0.000 description 1
- 108020001991 Protoporphyrinogen Oxidase Proteins 0.000 description 1
- 102000005135 Protoporphyrinogen oxidase Human genes 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 241000219094 Vitaceae Species 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- -1 cyclic imide Chemical class 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920005646 polycarboxylate Polymers 0.000 description 1
- 238000007781 pre-processing Methods 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/12—Powders or granules
- A01N25/14—Powders or granules wettable
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P13/00—Herbicides; Algicides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Dentistry (AREA)
- Toxicology (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention relates to the technical field of agriculture, and in particular provides a wettable powder containing flumioxazin and glufosinate-ammonium, a preparation method and application thereof. The wettable powder containing flumioxazin and glufosinate comprises the following preparation raw materials in percentage by mass: 66% of effective components, 1-10% of dispersing agent, 1-5% of wetting agent, 1% of complexing agent, 1.4% of fatty acid and the balance of filler; the active ingredients are flumioxazin and glufosinate-ammonium; the complexing agent is ethylenediamine tetraacetic acid and ammonium citrate; the fatty acids comprise palmitic acid and oleic acid. The wettable powder provided by the invention has stable performance during storage, higher efficacy, improves the herbicidal activity of herbicide, and prolongs the service life of the medicament.
Description
Technical Field
The invention relates to the technical field of agriculture, in particular to wettable powder containing flumioxazin and glufosinate-ammonium, a preparation method and application thereof.
Background
Flumioxazin (flumioxazin) is a cyclic imide herbicide developed by the japanese sumitomo chemical industry co. Flumioxazin is a protoporphyrinogen oxidase inhibitor, which is a contact-killing type selective herbicide used for preventing and killing broadleaf weeds of soybeans, cotton, grapes and other many crops. After flumioxazin is used for treating the surface layer of the soil, the pesticide is absorbed by the soil particles, a treatment layer is formed on the surface of the soil, and when weeds germinate, seedlings are withered by contacting the pesticide treatment layer.
The glufosinate is an organophosphorus herbicide, is a glutamine synthesis inhibitor, and is a nonselective contact herbicide; the weeding composition has a certain sucking effect and is often used for weeding in orchards and non-cultivated lands; for example, they are useful in potato fields for combating annual and perennial dicotyledonous plants, grassy weeds and sedge weeds.
The flumioxazin and the glufosinate have water solubility, but the water solubility of the flumioxazin and the glufosinate is different; the glufosinate-ammonium has strong water solubility and is dissolved in water, so that weather conditions need to be considered when the glufosinate-ammonium is applied. Also, both of them have water solubility, so that they are better in drug efficacy in high-temperature and high-humidity weather. No data in the prior art at present mention that the wettable powder containing flumioxazin and glufosinate is prepared by taking the water solubility difference between the flumioxazin and the glufosinate into consideration.
Patent CN113424834a relates to a 77% flumioxazin-glufosinate-ammonium dispersible granule, which effectively expands weed control spectrum, improves weed control activity of herbicide, remarkably reduces dosage of herbicide, reduces resistance of weed to medicament, delays resistance of weed to single medicament, improves control effect of resistant weed, prolongs service life of medicament, and reduces environmental pressure. More of the patent also compounds two original medicines to delay drug resistance, but the detailed physical property analysis of the two components is not carried out, so that the optimal drug effect of the two compounds is enlarged.
Aiming at the situation, the invention provides wettable powder containing flumioxazin and glufosinate-ammonium, a preparation method and application thereof.
Disclosure of Invention
The invention provides a wettable powder containing flumioxazin and glufosinate-ammonium, which comprises the following preparation raw materials in percentage by mass: 60% of flumioxazin, 6% of glufosinate, 6% of dispersing agent, 2.5% of wetting agent, 1% of complexing agent, 1.4% of fatty acid, 3% of white carbon black and the balance of talcum powder;
the complexing agent is ethylenediamine tetraacetic acid and ammonium citrate; and the mass ratio of the ethylenediamine tetraacetic acid to the ammonium citrate is 1:1;
the wetting agent comprises an anhydrous fast T wetting agent and sodium succinate sulfonate; and the mass ratio is 3:2;
the fatty acids comprise palmitic acid and oleic acid; and the mass ratio is 2:1, a step of;
the dispersant comprises a naphthalene sulfonate dispersant and a sodium methylene naphthalene sulfonate dispersant.
The second aspect of the invention provides the wettable powder containing flumioxazin and glufosinate-ammonium, which is used for early post-emergence weeding of cereal crops.
The third aspect of the invention provides a preparation method of the wettable powder containing flumioxazin and glufosinate, which comprises the following steps:
s01, mixing glufosinate and a complexing agent, adding fatty acid, and stirring and mixing;
s02, mixing flumioxazin, a dispersing agent and a filler, performing jet milling, adding a wetting agent after fineness is qualified, and performing secondary mixing on glufosinate after the treatment in the step S01 to obtain the wettable powder.
By adopting the technical scheme, the invention has the following beneficial effects:
the wettable powder provided by the invention has stable storage performance, higher efficacy, improves the herbicidal activity of the herbicide, and prolongs the service life of the medicament.
Detailed Description
The following description of the present invention will be made clearly and fully, and it is apparent that the embodiments described are some, but not all, of the embodiments of the present invention. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
The invention provides a wettable powder containing flumioxazin and glufosinate-ammonium, which comprises the following preparation raw materials in percentage by mass: 66% of effective components, 1-10% of dispersing agent, 1-5% of wetting agent, 1% of complexing agent, 1.4% of fatty acid and the balance of filler;
in a preferred embodiment, the dispersant is one or more selected from the group consisting of block polyether dispersants, polyether sulfate dispersants, naphthalene sulfonate dispersants, and polycarboxylate dispersants.
More preferably, the dispersant comprises naphthalene sulfonate dispersant and NNO (sodium methylene naphthalene sulfonate) dispersant; wherein the naphthalene sulfonate dispersant is purchased from akzo nobel morwet d-425 at a mass percent of 4%; the NNO (sodium methylene naphthalene sulfonate) dispersant is purchased from the chemical industry of Rong Yi Suzhou, and the mass percentage is 2%.
In a preferred mode, the wetting agent is selected from one or more of naphthalene sulfonate wetting agents, polyoxyethylene ether wetting agents, dicarboxylic ester sodium sulfonate wetting agents and fatty alcohol polyoxyethylene ether sulfate wetting agents.
More preferably, the wetting agent comprises an anhydrous fast T wetting agent purchased from chemical industry in guangzhou, 1.5 mass percent; the sodium succinate sulfonate was purchased from Triton-GR-7N, dow, 1% by mass.
Complexing agent, the complexing agent comprises ethylenediamine tetraacetic acid and ammonium citrate, wherein the mass percentage of ethylenediamine tetraacetic acid is 0.5%, and the mass percentage of ammonium citrate is 0.5%.
Fatty acid, wherein the fatty acid comprises palmitic acid and oleic acid, and the mass ratio of the palmitic acid to the oleic acid is 2:1, the comprehensive mass percentage is 1.4%.
As a preferred mode, the filler comprises white carbon black and talcum powder, and the weight percentage of the white carbon black is 3%, and the filler is purchased from Yingzhang AEROSIL200; talcum powder is added to 100%, and is purchased from Suzhou Jian Hui-thrown mineral new material.
The second surface of the invention provides a preparation method of the wettable powder containing flumioxazin and glufosinate-ammonium, which comprises the following steps:
s01, mixing glufosinate and a complexing agent, adding fatty acid, and stirring and mixing;
s02, mixing flumioxazin, a dispersing agent and a filler, performing jet milling, adding a wetting agent after fineness is qualified, and performing secondary mixing on glufosinate after the treatment in the step S01 to obtain the wettable powder.
The third aspect of the invention provides the wettable powder containing flumioxazin and glufosinate-ammonium, which is used for early post-emergence weeding of cereal crops.
Firstly, mixing a complexing agent and glufosinate, and preprocessing the glufosinate; and then mixing with the rest components; when in use, the water-based emulsion is mixed with water, and the phenomena of overlarge particle size and difficult wetting of raw medicines can not occur. Meanwhile, the water solubility of the flumioxazin and the glufosinate-ammonium are not close; meanwhile, as the wettable powder needs to be mixed with water for spraying when in use, the wettable powder then acts on crops. However, in the case of the type of preparation prepared as wettable powder, if both raw materials are subjected to jet milling treatment at the same time, it is easy to cause that the product particles after jet milling of glufosinate are small, and thus wetting is difficult. Thus, the common treatment is to perform the preparation separately, so that it is possible to avoid making more difficult the preparation.
Similarly, the difference in wettability and the time of action are different, and the two are both water-soluble to some extent, so that if the difference is large, the effect of 1+1>2 cannot be obtained between the two. In addition, the sensitivity of the two to the environment is not on the same standard, the glufosinate is sensitive to the humidity, and the flumioxazin is sensitive to the temperature. In the daily planting environment, the high-temperature and high-humidity environment rarely exists for a long time, and even in different areas, such as the north, the northwest, the south and the like, the humidity and the temperature are different.
After the compound preparation with higher wettability and storage stability is prepared by the invention, the drug effect is also very advantageous by the design of the whole formula. The invention adopts the compound complexing agent to complex with glufosinate and then prepare with flumioxazin, thereby being capable of preparing WP together and simultaneously effectively avoiding the phenomenon of difficult wetting in the later period.
In addition, the fast T is selected as the penetrating agent, and the principle is that the surfactant is reduced, so that the fast T is easy to wash in sudden rainy days and has an influence on the attachment of leaf surfaces. The inventor finds that the adhesive force of the product can be improved by selecting saturated fatty acid and unsaturated fatty acid and adding fast T, so that the effect of fast weeding is achieved. However, the invention discovers that adding partial saturated or unsaturated fatty acid into the formula can reduce the dispersion effect, and when the chelating agent is ethylenediamine tetraacetic acid, the phosphonic acid group on the glufosinate can form a single-layer complex with the chelating agent, and the carboxyl at the other end can be free at the interface of gas and liquid, so that the similar effect of surface activity can be achieved, and the defect of saturated fatty acid is overcome.
The invention is further illustrated with reference to specific embodiments.
Example 1
The embodiment provides a wettable powder containing flumioxazin and glufosinate, which comprises raw materials of 60% of flumioxazin, 6% of glufosinate, 6% of dispersing agent, 2.5% of wetting agent, 1% of complexing agent, 1.4% of fatty acid, 3% of white carbon black, 1% of complexing agent and the balance of talcum powder.
Wherein the dispersant comprises naphthalene sulfonate dispersant and NNO (sodium methylene naphthalene sulfonate) dispersant; wherein the naphthalene sulfonate dispersant is purchased from Akzo Nobel Morwet D-425, and the mass percentage of the naphthalene sulfonate dispersant is 4 percent of the preparation raw material; the NNO (sodium methylene naphthalene sulfonate) dispersant is purchased from the chemical industry of Rong Yi Cheng Zhu Su, and the mass percentage of the NNO (sodium methylene naphthalene sulfonate) dispersant is 2%.
The wetting agent comprises an anhydrous fast T wetting agent and sodium succinate sulfonate, wherein the anhydrous fast T wetting agent is purchased from chemical industry in Guangzhou, and the mass percentage of the wetting agent is 1.5 percent of the preparation raw materials; the sodium succinate sulfonate is purchased from Triton-GR-7N of Dow, and the mass percentage of the sodium succinate sulfonate to the preparation raw material is 1%.
The complexing agent comprises ethylenediamine tetraacetic acid and ammonium citrate, wherein the mass of the ethylenediamine tetraacetic acid accounts for 0.5% of the mass of the preparation raw materials, and the mass of the ammonium citrate accounts for 0.5% of the mass of the preparation raw materials.
The fatty acid comprises palmitic acid and oleic acid, and the mass ratio of the palmitic acid to the oleic acid is 2:1, the comprehensive mass accounts for 1.4 percent of the preparation raw materials.
The embodiment provides a preparation method of the wettable powder, which comprises the following steps:
s01, after the glufosinate and the complexing agent are mixed, a small amount of water is sprayed so as to facilitate the mixing of the glufosinate and the complexing agent, and then fatty acid is added, and stirring and mixing are performed;
s02, mixing flumioxazin, a dispersing agent and a filler, performing jet milling, adding a wetting agent after fineness is qualified, and performing secondary mixing on the treated glufosinate-ammonium to obtain the wettable powder.
Example 2
The embodiment provides wettable powder containing flumioxazin and glufosinate, which comprises 60% of flumioxazin, 6% of glufosinate, 6% of dispersing agent, 2.5% of wetting agent, 1.4% of fatty acid, 3% of white carbon black and the balance of talcum powder.
Wherein the dispersant comprises naphthalene sulfonate dispersant and NNO (sodium methylene naphthalene sulfonate) dispersant; wherein the naphthalene sulfonate dispersant is purchased from Akzo Nobel Morwet D-425, and the mass percentage of the naphthalene sulfonate dispersant is 4 percent of the preparation raw material; the NNO (sodium methylene naphthalene sulfonate) dispersant is purchased from the chemical industry of Rong Yi Cheng Zhu Su, and the mass percentage of the NNO (sodium methylene naphthalene sulfonate) dispersant is 2%.
The wetting agent comprises an anhydrous fast T wetting agent and sodium succinate sulfonate, wherein the anhydrous fast T wetting agent is purchased from chemical industry in Guangzhou, and the mass percentage of the wetting agent is 1.5 percent of the preparation raw materials; the sodium succinate sulfonate is purchased from Triton-GR-7N of Dow, and the mass percentage of the sodium succinate sulfonate to the preparation raw material is 1%.
The fatty acid comprises palmitic acid and oleic acid, and the mass ratio of the palmitic acid to the oleic acid is 2:1, the comprehensive mass percentage is 1.4%.
The embodiment provides a preparation method of the wettable powder, which comprises the following steps:
mixing glufosinate, fatty acid, flumioxazin, dispersing agent and filler, performing jet milling, adding wetting agent after fineness is qualified, and performing secondary mixing on the treated glufosinate to obtain the wettable powder.
Example 3
The embodiment provides wettable powder containing flumioxazin and glufosinate, which comprises 60% of flumioxazin, 6% of glufosinate, 6% of dispersing agent, 2.5% of wetting agent, 1.4% of fatty acid, 3% of white carbon black and the balance of talcum powder.
Wherein the dispersant comprises naphthalene sulfonate dispersant and NNO (sodium methylene naphthalene sulfonate) dispersant; wherein the naphthalene sulfonate dispersant is purchased from Akzo Nobel Morwet D-425, and the mass percentage of the naphthalene sulfonate dispersant is 4 percent of the preparation raw material; the NNO (sodium methylene naphthalene sulfonate) dispersant is purchased from the chemical industry of Rong Yi Cheng Zhu Su, and the mass percentage of the NNO (sodium methylene naphthalene sulfonate) dispersant is 2%.
The wetting agent comprises an anhydrous fast T wetting agent and sodium succinate sulfonate, wherein the anhydrous fast T wetting agent is purchased from chemical industry in Guangzhou, and the mass percentage of the wetting agent is 1.5 percent of the preparation raw materials; the sodium succinate sulfonate is purchased from Triton-GR-7N of Dow, and the mass percentage of the sodium succinate sulfonate to the preparation raw material is 1%.
The fatty acid comprises palmitic acid and oleic acid, and the mass ratio of the palmitic acid to the oleic acid is 2:1, the comprehensive mass accounts for 1.4 percent of the preparation raw materials.
The embodiment provides a preparation method of the wettable powder, which comprises the following steps:
s01, mixing glufosinate and fatty acid under stirring;
s02, mixing flumioxazin, a dispersing agent and a filler, performing jet milling, adding a wetting agent after fineness is qualified, and performing secondary mixing on the treated glufosinate-ammonium to obtain the wettable powder.
Example 4
The embodiment provides wettable powder containing flumioxazin and glufosinate, which comprises 60% of flumioxazin, 6% of glufosinate, 6% of dispersing agent, 2.5% of wetting agent, 1% of complexing agent, 1.4% of fatty acid, 3% of white carbon black and the balance of talcum powder.
Wherein the dispersant comprises naphthalene sulfonate dispersant and NNO (sodium methylene naphthalene sulfonate) dispersant; wherein the naphthalene sulfonate dispersant is purchased from Akzo Nobel Morwet D-425, and the mass percentage of the naphthalene sulfonate dispersant is 4 percent of the preparation raw material; the NNO (sodium methylene naphthalene sulfonate) dispersant is purchased from the chemical industry of Rong Yi Cheng Zhu Su, and the mass percentage of the NNO (sodium methylene naphthalene sulfonate) dispersant is 2%.
The wetting agent comprises an anhydrous fast T wetting agent and sodium succinate sulfonate, wherein the anhydrous fast T wetting agent is purchased from chemical industry in Guangzhou, and the mass percentage of the wetting agent is 1.5 percent of the preparation raw materials; the sodium succinate sulfonate is purchased from Triton-GR-7N of Dow, and the mass percentage of the sodium succinate sulfonate to the preparation raw material is 1%.
The complexing agent is ethylenediamine tetraacetic acid.
The fatty acid comprises palmitic acid and oleic acid, and the mass ratio of the palmitic acid to the oleic acid is 2:1, the comprehensive mass accounts for 1.4 percent of the preparation raw materials.
The embodiment provides a preparation method of the wettable powder, which comprises the following steps:
s01, after the glufosinate and the complexing agent are mixed, a small amount of water is sprayed so as to facilitate the mixing of the glufosinate and the complexing agent, and then fatty acid is added, and stirring and mixing are performed;
s02, mixing flumioxazin, a dispersing agent and a filler, performing jet milling, adding a wetting agent after fineness is qualified, and performing secondary mixing on the treated glufosinate-ammonium to obtain the wettable powder.
Example 5
The embodiment provides wettable powder containing flumioxazin and glufosinate, which comprises 60% of flumioxazin, 6% of glufosinate, 6% of dispersing agent, 2.5% of wetting agent, 1% of complexing agent, 1.4% of fatty acid, 3% of white carbon black and the balance of talcum powder.
Wherein the dispersant comprises naphthalene sulfonate dispersant and NNO (sodium methylene naphthalene sulfonate) dispersant; wherein the naphthalene sulfonate dispersant is purchased from Akzo Nobel Morwet D-425, and the mass percentage of the naphthalene sulfonate dispersant is 4 percent of the preparation raw material; the NNO (sodium methylene naphthalene sulfonate) dispersant is purchased from the chemical industry of Rong Yi Cheng Zhu Su, and the mass percentage of the NNO (sodium methylene naphthalene sulfonate) dispersant is 2%.
The wetting agent comprises an anhydrous fast T wetting agent and sodium succinate sulfonate, wherein the anhydrous fast T wetting agent is purchased from chemical industry in Guangzhou, and the mass percentage of the wetting agent is 1.5 percent of the preparation raw materials; the sodium succinate sulfonate is purchased from Triton-GR-7N of Dow, and the mass percentage of the sodium succinate sulfonate to the preparation raw material is 1%.
The complexing agent comprises ethylenediamine tetraacetic acid and ammonium citrate, wherein the mass of the ethylenediamine tetraacetic acid accounts for 0.5% of the mass of the preparation raw materials, and the mass of the ammonium citrate accounts for 0.5% of the mass of the preparation raw materials.
The fatty acid comprises palmitic acid and oleic acid, and the mass ratio of the palmitic acid to the oleic acid is 2:1, the comprehensive mass accounts for 1.4 percent of the preparation raw materials.
The embodiment provides a preparation method of the wettable powder, which comprises the following steps:
and mixing flumioxazin, glufosinate, complexing agent, dispersing agent, fatty acid, wetting agent and filler, performing jet milling, and adding the treated glufosinate to perform secondary mixing after fineness is qualified to obtain the wettable powder.
Example 6
The embodiment provides wettable powder containing flumioxazin and glufosinate, which comprises 60% of flumioxazin, 6% of glufosinate, 6% of dispersing agent, 2.5% of wetting agent, 1% of complexing agent, 3% of white carbon black and the balance of talcum powder.
Wherein the dispersant comprises naphthalene sulfonate dispersant and NNO (sodium methylene naphthalene sulfonate) dispersant; wherein the naphthalene sulfonate dispersant is purchased from Akzo Nobel Morwet D-425, and the mass percentage of the naphthalene sulfonate dispersant is 4 percent of the preparation raw material; the NNO (sodium methylene naphthalene sulfonate) dispersant is purchased from the chemical industry of Rong Yi Cheng Zhu Su, and the mass percentage of the NNO (sodium methylene naphthalene sulfonate) dispersant is 2%.
The wetting agent comprises an anhydrous fast T wetting agent and sodium succinate sulfonate, wherein the anhydrous fast T wetting agent is purchased from chemical industry in Guangzhou, and the mass percentage of the wetting agent is 1.5 percent of the preparation raw materials; the sodium succinate sulfonate is purchased from Triton-GR-7N of Dow, and the mass percentage of the sodium succinate sulfonate to the preparation raw material is 1%.
The complexing agent comprises ethylenediamine tetraacetic acid and ammonium citrate, wherein the mass of the ethylenediamine tetraacetic acid accounts for 0.5% of the mass of the preparation raw materials, and the mass of the ammonium citrate accounts for 0.5% of the mass of the preparation raw materials.
The embodiment provides a preparation method of the wettable powder, which comprises the following steps:
s01, after the glufosinate and the complexing agent are mixed, a small amount of water is sprayed so as to facilitate the mixing of the glufosinate and the complexing agent;
s02, mixing flumioxazin, a dispersing agent and a filler, performing jet milling, adding a wetting agent after fineness is qualified, and performing secondary mixing on the treated glufosinate-ammonium to obtain the wettable powder.
Example 7
The embodiment provides wettable powder containing flumioxazin and glufosinate, which comprises 60% of flumioxazin, 6% of glufosinate, 6% of dispersing agent, 2.5% of wetting agent, 1% of complexing agent, 3% of white carbon black and the balance of talcum powder.
Wherein the dispersant comprises naphthalene sulfonate dispersant and NNO (sodium methylene naphthalene sulfonate) dispersant; wherein the naphthalene sulfonate dispersant is purchased from Akzo Nobel Morwet D-425, and the mass percentage of the naphthalene sulfonate dispersant is 4 percent of the preparation raw material; the NNO (sodium methylene naphthalene sulfonate) dispersant is purchased from the chemical industry of Rong Yi Cheng Zhu Su, and the mass percentage of the NNO (sodium methylene naphthalene sulfonate) dispersant is 2%.
The wetting agent comprises an anhydrous fast T wetting agent and sodium succinate sulfonate, wherein the anhydrous fast T wetting agent is purchased from chemical industry in Guangzhou, and the mass percentage of the wetting agent is 1.5 percent of the preparation raw materials; the sodium succinate sulfonate is purchased from Triton-GR-7N of Dow, and the mass percentage of the sodium succinate sulfonate to the preparation raw material is 1%.
The complexing agent is ethylenediamine tetraacetic acid.
The fatty acid comprises palmitic acid and oleic acid, and the mass ratio of the palmitic acid to the oleic acid is 2:1, the comprehensive mass percentage is 1.4%.
The embodiment provides a preparation method of the wettable powder, which comprises the following steps:
s01, after the glufosinate and the complexing agent are mixed, a small amount of water is sprayed so as to facilitate the mixing of the glufosinate and the complexing agent, and then fatty acid is added, and stirring and mixing are performed;
s02, mixing flumioxazin, a dispersing agent and a filler, performing jet milling, adding a wetting agent after fineness is qualified, and performing secondary mixing on the treated glufosinate-ammonium to obtain the wettable powder.
Performance testing
1. Test 1: the measurement of the heat storage stability is carried out by referring to a GB/T19136-2003 pesticide heat storage stability measurement method; the low temperature stability measurement is performed by referring to the GB/T19137-2003 pesticide low temperature stability measurement method. Judgment standard: qualified: the decomposition rate is less than or equal to 5 percent; disqualification: the decomposition rate is more than 5 percent.
2. Test 2: drug efficacy test
Table 1 test results of test 1
From the above examples, the difference between example 2 and example 1 is that the preparation raw material in example 2 was not added with complexing agent, and the preparation method was prepared by pulverizing glufosinate-ammonium and flumioxazin together; example 3 differs from example 1 in that no complexing agent was added to the preparation starting material; example 4 differs from example 1 in that the complexing agent in the preparation of example 4 does not comprise ammonium citrate; example 5 differs from example 1 in that glufosinate was prepared by crushing glufosinate and flumioxazin together, and glufosinate was not treated in advance; example 6 differs from example 1 in that the preparation starting material of example 6 does not contain fatty acids; example 7 differs from example 1 in that the preparation starting material of example 7 does not comprise fatty acids and ammonium citrate.
From the above, the complexing agent and the glufosinate are mixed firstly, and the glufosinate is pretreated; and then mixing with the rest components; when in use, the water-based emulsion is mixed with water, and the phenomena of overlarge particle size and difficult wetting of raw medicines can not occur. The invention adopts the compound complexing agent to complex with glufosinate and then prepare with flumioxazin, thereby being capable of preparing WP together and simultaneously effectively avoiding the phenomenon of difficult wetting in the later period. According to the invention, the dispersing effect is reduced by adding partial saturated or unsaturated fatty acid into the formula, and if the chelating agent is ethylenediamine tetraacetic acid, the phosphonic acid group on the glufosinate can form a single-layer complex with the chelating agent, and meanwhile, the carboxyl at the other end can be free at the interface of gas and liquid, so that the similar effect of surface activity can be achieved, and the defect of saturated fatty acid is overcome.
Efficacy test of 66% flumioxazin-glufosinate wettable powder for preventing and controlling non-cultivated land weeds in field.
The application method and the water consumption are as follows: the stems and leaves are sprayed, the spraying is uniform, and the water consumption is 750 liters per hectare. The weed starts to be used when the height of the weeds is 10-30cm, and the proper dosage is 396 g/hectare of 66% flumioxazin-glufosinate wettable powder active ingredient.
Selection of test subjects weeds
Target 1, cirsium setosum (Willd.) MB., target 2, sucedasala (Linn.) Pall, target 3, digitataasanguinalis (L.) Scop, and target 4, setairavidis (L.) Bcauv.
The control medicament is 200g/L glufosinate-ammonium aqua, and the registration number is: PD20132310, beijing Bonong chemical technology Co., ltd.
Blank control treatment was set.
The liquid medicine was uniformly sprayed on the front and back sides of plant leaves using an AGROLEXSPRAYERJACTOHD400 Linong 16L backpack sprayer (manufactured by Singapore private Co., ltd., using a conical spray head, adding a 1 Pa constant pressure valve, and a flow rate of 630 ml/min). The medicine is applied once in 28 days of 6 months. Weather data: the test is carried out in the shade on the same day, the temperature is 20.0-25.0 ℃, the average temperature is 28.0 ℃ during the test, the highest temperature is 30 ℃, the lowest temperature is 18.0 ℃, and the weather is better in the test stage.
The test site is arranged in a modern agriculture development area of Feichong City of Shandong province, the area of the test land is 10 mu, the soil type is brown soil, the organic matter content is 11.2%, and the test area is barren land. The weed distribution was uniform in all test plots.
Investigation time and times
Investigation was performed 7 days, 14 days, and 30 days after administration, respectively, for a total of 3 times.
Investigation method
The total number of plants per weed was investigated 14 days after the drug, the total number of plants and fresh weight per weed was investigated 30 days after the drug, 4 spots were randomly selected per cell, and 0.25m per spot. Gramineous weeds were checked for scores.
Drug effect calculation method
Control effect% = (number of active grasses in control area-number of active grasses in agent treatment area)/number of active grasses in control area ×100%.
The efficacy test was performed on examples 1, 2, 4, and 6, and the test results were as follows:
table 2 66% flumioxazin-glufosinate-ammonium wettable powder for controlling non-cultivated land weed strain control effect (%) -14 d after drug administration
Table 3 66% flumioxazin-glufosinate-ammonium wettable powder for controlling non-cultivated land weed strain control effect (%) -30 d after drug administration
Finally, it should be noted that: the above embodiments are only for illustrating the technical solution of the present invention, and not for limiting the same; although the invention has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: the technical scheme described in the foregoing embodiments can be modified or some or all of the technical features thereof can be replaced by equivalents; such modifications and substitutions do not depart from the spirit of the invention.
Claims (2)
1. The wettable powder containing flumioxazin and glufosinate is characterized by comprising the following preparation raw materials in percentage by mass: 60% of flumioxazin, 6% of glufosinate, 6% of dispersing agent, 2.5% of wetting agent, 1% of complexing agent, 1.4% of fatty acid, 3% of white carbon black and the balance of talcum powder;
the complexing agent is ethylenediamine tetraacetic acid and ammonium citrate; and the mass ratio of the ethylenediamine tetraacetic acid to the ammonium citrate is 1:1;
the wetting agent is anhydrous fast T wetting agent and sodium succinate sulfonate; and the mass ratio is 3:2;
the fatty acid is palmitic acid and oleic acid; and the mass ratio is 2:1, a step of;
the dispersing agent is naphthalene sulfonate dispersing agent and methylene naphthalene sulfonate dispersing agent;
the preparation method of the wettable powder containing flumioxazin and glufosinate-ammonium comprises the following steps:
s01, mixing glufosinate and a complexing agent, adding fatty acid, and stirring and mixing;
s02, mixing flumioxazin, a dispersing agent and a filler, performing jet milling, adding a wetting agent after fineness is qualified, and performing secondary mixing on glufosinate after the treatment in the step S01 to obtain the wettable powder.
2. Wettable powder comprising flumioxazin and glufosinate according to claim 1 for use in early post-emergence weeding of cereal crops.
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| CN112690283A (en) * | 2019-10-23 | 2021-04-23 | 沈阳中化农药化工研发有限公司 | Herbicidal composition containing phenyl isoxazolines with optical activity and application |
| CN113424834A (en) * | 2021-05-08 | 2021-09-24 | 安徽省益农化工有限公司 | 77% flumioxazin-glufosinate dispersible granule |
| WO2022229654A1 (en) * | 2021-04-30 | 2022-11-03 | UPL Corporation Limited | Herbicidal compositions with enhanced soil mobility |
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| JP2001139401A (en) * | 1999-11-12 | 2001-05-22 | Sumitomo Chem Co Ltd | Granular wettable powder |
| CN107624780A (en) * | 2016-07-19 | 2018-01-26 | 山东潍坊润丰化工股份有限公司 | A kind of glufosinate-ammonium water-soluble granule |
| CN109392946A (en) * | 2017-08-15 | 2019-03-01 | 海利尔药业集团股份有限公司 | A kind of Herbicidal combinations containing glufosinate-ammonium and flumioxazin |
| CN112690283A (en) * | 2019-10-23 | 2021-04-23 | 沈阳中化农药化工研发有限公司 | Herbicidal composition containing phenyl isoxazolines with optical activity and application |
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