CN117158432A - Herbicide containing mequindox, acifluorfen and bentazone and preparation method thereof - Google Patents
Herbicide containing mequindox, acifluorfen and bentazone and preparation method thereof Download PDFInfo
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- CN117158432A CN117158432A CN202310986197.XA CN202310986197A CN117158432A CN 117158432 A CN117158432 A CN 117158432A CN 202310986197 A CN202310986197 A CN 202310986197A CN 117158432 A CN117158432 A CN 117158432A
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- acifluorfen
- bentazone
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- 239000004009 herbicide Substances 0.000 title claims abstract description 47
- 239000005476 Bentazone Substances 0.000 title claims abstract description 42
- NUFNQYOELLVIPL-UHFFFAOYSA-N acifluorfen Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 NUFNQYOELLVIPL-UHFFFAOYSA-N 0.000 title claims abstract description 42
- ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 title claims abstract description 42
- CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzidamine Natural products C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 title claims abstract description 42
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 40
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- CUJMCPPBTUATEJ-UHFFFAOYSA-N 1-(3-methyl-4-oxido-1-oxoquinoxalin-1-ium-2-yl)ethanone Chemical compound C1=CC=C2[N+](=O)C(C(=O)C)=C(C)N([O-])C2=C1 CUJMCPPBTUATEJ-UHFFFAOYSA-N 0.000 title claims description 30
- 229920001661 Chitosan Polymers 0.000 claims abstract description 72
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000003094 microcapsule Substances 0.000 claims abstract description 30
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 claims abstract description 28
- 229930002875 chlorophyll Natural products 0.000 claims abstract description 25
- 235000019804 chlorophyll Nutrition 0.000 claims abstract description 25
- 239000008367 deionised water Substances 0.000 claims abstract description 25
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 25
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000000843 powder Substances 0.000 claims abstract description 16
- 235000017788 Cydonia oblonga Nutrition 0.000 claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- 239000000839 emulsion Substances 0.000 claims abstract description 14
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 claims abstract description 11
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims abstract description 9
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims abstract description 9
- 239000004372 Polyvinyl alcohol Substances 0.000 claims abstract description 9
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims abstract description 9
- 229920002451 polyvinyl alcohol Polymers 0.000 claims abstract description 9
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 8
- 229920000570 polyether Polymers 0.000 claims abstract description 8
- 229920002545 silicone oil Polymers 0.000 claims abstract description 8
- 239000012874 anionic emulsifier Substances 0.000 claims abstract description 7
- 239000000243 solution Substances 0.000 claims description 67
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 30
- 238000003756 stirring Methods 0.000 claims description 29
- 230000003213 activating effect Effects 0.000 claims description 20
- TURHTASYUMWZCC-UHFFFAOYSA-N Olaquindox [BAN:INN] Chemical compound C1=CC=C2N([O-])C(C)=C(C(=O)NCCO)[N+](=O)C2=C1 TURHTASYUMWZCC-UHFFFAOYSA-N 0.000 claims description 17
- 229950010210 olaquindox Drugs 0.000 claims description 17
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 14
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims description 11
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims description 11
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 claims description 11
- 238000001816 cooling Methods 0.000 claims description 10
- 230000001105 regulatory effect Effects 0.000 claims description 10
- SXGZJKUKBWWHRA-UHFFFAOYSA-N 2-(N-morpholiniumyl)ethanesulfonate Chemical compound [O-]S(=O)(=O)CC[NH+]1CCOCC1 SXGZJKUKBWWHRA-UHFFFAOYSA-N 0.000 claims description 7
- 238000001914 filtration Methods 0.000 claims description 7
- 239000012188 paraffin wax Substances 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- 229920004890 Triton X-100 Polymers 0.000 claims description 6
- 239000013504 Triton X-100 Substances 0.000 claims description 6
- 238000000502 dialysis Methods 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 229930002869 chlorophyll b Natural products 0.000 claims description 4
- NSMUHPMZFPKNMZ-VBYMZDBQSA-M chlorophyll b Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C=O)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 NSMUHPMZFPKNMZ-VBYMZDBQSA-M 0.000 claims description 4
- 230000014759 maintenance of location Effects 0.000 claims description 4
- 238000010298 pulverizing process Methods 0.000 claims description 4
- 229960005294 triamcinolone Drugs 0.000 claims description 4
- GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical group O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 claims description 4
- 229930002868 chlorophyll a Natural products 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 2
- 229960002117 triamcinolone acetonide Drugs 0.000 claims description 2
- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 claims description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract description 40
- 241000192043 Echinochloa Species 0.000 abstract description 11
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract description 9
- 230000002147 killing effect Effects 0.000 abstract description 6
- 230000002349 favourable effect Effects 0.000 abstract description 3
- 206010034972 Photosensitivity reaction Diseases 0.000 abstract description 2
- 238000005354 coacervation Methods 0.000 abstract description 2
- 239000000575 pesticide Substances 0.000 abstract description 2
- 230000036211 photosensitivity Effects 0.000 abstract description 2
- RONWGALEIBILOG-VMJVVOMYSA-N quinine sulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 RONWGALEIBILOG-VMJVVOMYSA-N 0.000 abstract 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 239000008096 xylene Substances 0.000 description 5
- 239000005614 Quizalofop-P-ethyl Substances 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- OSUHJPCHFDQAIT-GFCCVEGCSA-N quizalofop-P-ethyl Chemical group C1=CC(O[C@H](C)C(=O)OCC)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 OSUHJPCHFDQAIT-GFCCVEGCSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- -1 aryl phenoxy propionic acid Chemical compound 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 244000037666 field crops Species 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- FCZYGJBVLGLYQU-UHFFFAOYSA-M sodium;2-[2-[2-[4-(2,4,4-trimethylpentan-2-yl)phenoxy]ethoxy]ethoxy]ethanesulfonate Chemical group [Na+].CC(C)(C)CC(C)(C)C1=CC=C(OCCOCCOCCS([O-])(=O)=O)C=C1 FCZYGJBVLGLYQU-UHFFFAOYSA-M 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
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- 230000009885 systemic effect Effects 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
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- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention discloses a herbicide containing refined quince, acifluorfen and bentazone and a preparation method thereof, belonging to the technical field of pesticides, and comprising chitosan coated refined quince microcapsule, acifluorfen, bentazone, polyether modified silicone oil, p-hydroxybenzoic acid, anionic emulsifier, hydroxyethyl cellulose, polyvinyl alcohol and deionized water; after the chitosan is grafted with chlorophyll by reaction, the solution of chlorophyll grafted chitosan powder is mixed with refined quinoline emulsion, and as the solubility of refined quinoline in dimethylbenzene is far greater than that of refined quinoline in water, the refined quinoline is basically coated in the chlorophyll grafted chitosan after the chitosan coated refined quinoline microcapsule is prepared by a single coacervation method; the p-hydroxybenzoic acid has photosensitivity, is favorable for increasing the photostability of the chitosan coated refined quine microcapsule, and can basically recover the photocleavable property of the chitosan coated refined quine microcapsule after the herbicide is diluted for use, thereby playing a role in killing barnyard grass.
Description
Technical Field
The invention belongs to the technical field of pesticides, and particularly relates to a herbicide containing mequindox, acifluorfen and bentazone and a preparation method thereof.
Background
Herbicides are agents which thoroughly or selectively kill weeds and are used to kill or inhibit plant growth and are also known as herbicides.
The quizalofop-p-ethyl is a low-toxicity herbicide with aryl phenoxy propionic acid selectivity and systemic conduction. The action mechanism of the weed killer is that the weed killer is absorbed by stem leaves of weeds, is conducted upwards and downwards in a plant body, is accumulated on top and intermediate meristems, and inhibits the synthesis of cell fatty acid, so that the weeds are necrotized. The acifluorfen is a contact-killing type selective post-emergence herbicide, can be absorbed by weed stems and leaves, is not absorbed by roots in soil, is easily decomposed by microorganisms, cannot be used for soil treatment, and is safe for soybeans. Mainly preventing broadleaf grass. The bentazone is a selective herbicide after seedling, has the advantages of high efficiency, wide herbicide controlling spectrum, low toxicity, no phytotoxicity, good compatibility with other herbicides and the like, and has good killing effect on various weeds of paddy and upland field crops.
The Chinese patent with the bulletin number of CN102265858B announces a mixed herbicide containing bentazone, acifluorfen and quizalofop-p-ethyl and application thereof, compared with a single herbicide, the mixed herbicide has the advantages of delaying the resistance of weeds, along with wide weeding spectrum, long duration and safety to soybeans and afterreap crops on the premise of improving the pesticide effect. But the effect of barnyard grass killing can be reduced after the refined quindox is compounded with bentazone and acifluorfen.
Disclosure of Invention
The invention aims to provide a herbicide containing mequindox, acifluorfen and bentazone, which solves the problem of poor effect of killing barnyard grass after the mequindox is compounded; and the second aim is to provide a preparation method of herbicide containing mequindox, acifluorfen and bentazone.
The aim of the invention can be achieved by the following technical scheme:
the herbicide containing the mequindox, the acifluorfen and the bentazone comprises the following components in parts by mass:
15-20 parts of chitosan coated refined olaquindox microcapsule, 4-8 parts of acifluorfen, 15-20 parts of bentazone, 15-20 parts of polyether modified silicone oil, 0.2-0.8 part of p-hydroxybenzoic acid, 2-4 parts of anionic emulsifier, 2-3 parts of hydroxyethyl cellulose, 1-2 parts of polyvinyl alcohol and 40-60 parts of deionized water.
Further, the anionic emulsifier is triton X-200 or triton X-750.
A preparation method of a herbicide containing mequindox, acifluorfen and bentazone comprises the following steps:
adding chitosan coated refined quince microcapsule, acifluorfen, bentazone, polyether modified silicone oil, parahydroxybenzoic acid, anionic emulsifier, hydroxyethyl cellulose, polyvinyl alcohol and deionized water into a stirrer, stirring for 15-20min under 1000-1500r/min and light-proof condition, and obtaining herbicide containing refined quince, acifluorfen and bentazone.
Further, the chitosan coated refined olaquindox microcapsule is prepared by the following steps:
step one: adding chitosan and acetic acid solution with mass fraction of 2-5% into a reaction kettle, stirring for 30-60min, and regulating pH value to 6+ -0.2 with sodium hydroxide solution to obtain chitosan solution;
step two: regulating the pH value of morpholine ethanesulfonic acid aqueous solution with the molar concentration of 10 mmo/L to 6+/-0.2 by using a sodium hydroxide solution with the mass fraction of 25%, then adding 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride and N-hydroxysuccinimide, stirring and dissolving, wherein 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride is used as an activating agent, and N-hydroxysuccinimide is used as an activating agent to obtain an activating solution;
step three: dissolving chlorophyll with dimethyl sulfoxide, adding into the activating solution, stirring at 20-25deg.C under dark condition for 4-5 hr, adding chitosan solution, stirring for 20-24 hr, transferring the reaction solution into dialysis bag with molecular retention of 10000-14000Da, dialyzing with deionized water for purification for 2-4 days, lyophilizing the dialyzed and purified solution, and pulverizing to obtain chlorophyll grafted chitosan powder;
step four: mixing and stirring triton X-100 serving as an emulsifier and deionized water, adding a refined quinol xylene solution with the mass fraction of 10% and solid paraffin, stirring for 2-3 hours at 75-80 ℃ and 1500-2000r/min, and cooling to obtain a refined quinol emulsion;
step five: dissolving chlorophyll grafted chitosan powder in acetic acid solution with mass fraction of 1% under the condition of light shielding, adding refined olaquindox emulsion, stirring at 60 ℃ under the condition of light shielding for reaction for 12-14h, cooling, filtering, washing with deionized water for 2-3 times, and drying to obtain the chitosan coated refined olaquindox microcapsule.
Further, the dosage ratio of chitosan to acetic acid solution is 0.1-0.15g:100-120mL;
further, the dosage ratio of the morpholine ethanesulfonic acid aqueous solution, the 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride and the N-hydroxysuccinimide is 50-60mL:0.55g:0.66g.
Further, the dosage ratio of chlorophyll, dimethyl sulfoxide, activating solution and chitosan solution is 0.25-0.5g:50-60mL:50-60mL:1-1.2L.
Further, chlorophyll is chlorophyll a or chlorophyll b.
Further, the dosage ratio of the triton X-100, the deionized water, the refined quinol xylene solution and the solid paraffin is 0.1-0.15g:20-30mL:20-25mL:0.3-0.4g.
Further, the dosage ratio of chlorophyll grafted chitosan powder, acetic acid solution and refined quinoline emulsion is 1-1.5g:50-60mL:50-60mL.
The invention has the beneficial effects that:
the herbicide containing the mequindox, the acifluorfen and the bentazone disclosed by the invention can kill various types of weeds at the same time, the mequindox is prepared into chitosan coated mequindox microcapsules and then compounded, and the chitosan coated mequindox microcapsules are gradually cracked to release active components of the mequindox after being irradiated by light, so that the effect of increasing the killing capacity of barnyard grass is facilitated, and the influence of direct compounding on the capacity of the mequindox to kill barnyard grass is avoided.
After the chitosan is grafted with chlorophyll by reaction, the solution of chlorophyll grafted chitosan powder is mixed with refined quinoline emulsion, and as the solubility of refined quinoline in dimethylbenzene is far greater than that of refined quinoline in water, the refined quinoline is basically coated in the chlorophyll grafted chitosan after the chitosan coated refined quinoline microcapsule is prepared by a single coacervation method; the p-hydroxybenzoic acid has photosensitivity, is favorable for increasing the photostability of the chitosan coated refined olaquindox microcapsule, and can basically recover the photocleavable property of the chitosan coated refined olaquindox microcapsule after the herbicide is diluted for use. The hydroxyethyl cellulose can increase the consistency of the herbicide, plays a role in tackifying together with the polyvinyl alcohol, is favorable for the chitosan coated refined quinoline microcapsule to be attached to the barnyard grass leaves, and increases the barnyard grass killing effect.
Detailed Description
The technical solutions of the embodiments of the present invention will be clearly and completely described below in conjunction with the embodiments of the present invention, and it is apparent that the described embodiments are only some embodiments of the present invention, not all embodiments. 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.
Example 1
The embodiment provides a herbicide containing mequindox, acifluorfen and bentazone, which comprises the following implementation steps:
step one: 10kg of chitosan and 10000L of acetic acid solution with mass fraction of 2% are added into a reaction kettle to be stirred for 30min, and the pH value is regulated to 6+/-0.2 by sodium hydroxide solution, thus obtaining chitosan solution.
Step two: the pH value of 500L morpholine ethanesulfonic acid water solution with the molar concentration of 10mmO L/L is regulated to 6+/-0.2 by using sodium hydroxide solution with the mass fraction of 25 percent, then 5.5kg of 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride and 6.6kg of N-hydroxysuccinimide are added, and the mixture is stirred and dissolved, wherein 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride is taken as an activating agent, and N-hydroxysuccinimide is taken as an activating agent, so as to obtain an activating solution.
Step three: dissolving 2.5kg of chlorophyll a with 500L of dimethyl sulfoxide, adding into 500L of activating solution, stirring at 20deg.C under dark condition for 4h, adding 10000L of chitosan solution, stirring for 20h, transferring the reaction solution into dialysis bag with molecular retention of 10000Da, dialyzing with deionized water for purification for 2 days, lyophilizing the dialysed and purified solution, and pulverizing to obtain chlorophyll grafted chitosan powder.
Step four: 10kg of triton X-100 serving as an emulsifier and 2000L of deionized water are stirred and mixed, 2000L of refined quinol xylene solution with the mass fraction of 10% and 30kg of solid paraffin are added, and stirring is carried out for 2 hours at 75 ℃ and 1500r/min, and cooling is carried out, so that refined quinol emulsion is obtained.
Step five: dissolving 1kg of chlorophyll grafted chitosan powder with 50L of acetic acid solution with the mass fraction of 1% under the light-shielding condition, adding 50L of refined quinoline emulsion, stirring at 60 ℃ under the light-shielding condition for reaction for 12 hours, cooling, filtering, washing with deionized water for 2 times, and drying to obtain the chitosan coated refined quinoline microcapsule.
Step six: 1.5kg of chitosan coated refined quince microcapsules, 0.4kg of acifluorfen, 1.5kg of bentazone, 1.5kg of polyether modified silicone oil, 0.02kg of parahydroxybenzoic acid, 0.2kg of triamcinolone X-200, 0.2kg of hydroxyethyl cellulose, 0.1kg of polyvinyl alcohol and 4kg of deionized water are added into a stirrer, and stirred for 15min under the conditions of 1000r/min and light shielding, so as to obtain the herbicide containing refined quince, acifluorfen and bentazone.
Example 2
The embodiment provides a herbicide containing mequindox, acifluorfen and bentazone, which comprises the following implementation steps:
step one: adding 12kg of chitosan and 11000L of acetic acid solution with the mass fraction of 3% into a reaction kettle, stirring for 45min, and regulating the pH value to 6+/-0.2 by using a sodium hydroxide solution to obtain the chitosan solution.
Step two: the pH value of 500L morpholine ethanesulfonic acid water solution with the molar concentration of 10mmO L/L is regulated to 6+/-0.2 by using sodium hydroxide solution with the mass fraction of 25 percent, then 5.5kg of 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride and 6.6kg of N-hydroxysuccinimide are added, and the mixture is stirred and dissolved, wherein 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride is taken as an activating agent, and N-hydroxysuccinimide is taken as an activating agent, so as to obtain an activating solution.
Step three: dissolving 3.5kg of chlorophyll b with 550L of dimethyl sulfoxide, adding into 550L of activating solution, stirring at 22 ℃ under the dark condition for 4.5h, then adding 11000L of chitosan solution, continuously stirring for 22h, transferring the reaction solution into a dialysis bag with the molecular cutoff of 12000Da, dialyzing and purifying with deionized water for 3 days, freeze-drying the dialysed and purified liquid, and crushing to obtain chlorophyll grafted chitosan powder.
Step four: 12kg of triton X-100 serving as an emulsifier and 2500L of deionized water are stirred and mixed, 2200L of refined quinol xylene solution with the mass fraction of 10% and 35kg of solid paraffin are added, stirring is carried out for 2.5 hours at 78 ℃ and 1800r/min, and cooling is carried out, thus obtaining refined quinol emulsion.
Step five: dissolving 1.2kg of chlorophyll grafted chitosan powder with 55L of acetic acid solution with mass fraction of 1% under the condition of light shielding, adding 55L of refined quinoline emulsion, stirring at 60 ℃ under the condition of light shielding for reaction for 13h, cooling, filtering, washing with deionized water for 2 times, and drying to obtain the chitosan coated refined quinoline microcapsule.
Step six: 1.8kg of chitosan coated refined quince microcapsules, 0.6kg of acifluorfen, 1.8kg of bentazone, 1.8kg of polyether modified silicone oil, 0.06kg of parahydroxybenzoic acid, 0.3kg of triamcinolone X-750, 0.25kg of hydroxyethyl cellulose, 0.15kg of polyvinyl alcohol and 5kg of deionized water are added into a stirrer, and stirred for 18min under the conditions of 1200r/min and light shielding, so as to obtain the herbicide containing refined quince, acifluorfen and bentazone.
Example 3
The embodiment provides a herbicide containing mequindox, acifluorfen and bentazone, which comprises the following implementation steps:
step one: 15kg of chitosan and 12000L of acetic acid solution with mass fraction of 5% are added into a reaction kettle, stirred for 60min, and pH value is regulated to 6+/-0.2 by sodium hydroxide solution, thus obtaining chitosan solution.
Step two: the pH value of 500L morpholine ethanesulfonic acid water solution with the molar concentration of 10mmO L/L is regulated to 6+/-0.2 by using sodium hydroxide solution with the mass fraction of 25 percent, then 5.5kg of 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride and 6.6kg of N-hydroxysuccinimide are added, and the mixture is stirred and dissolved, wherein 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride is taken as an activating agent, and N-hydroxysuccinimide is taken as an activating agent, so as to obtain an activating solution.
Step three: dissolving 5kg of chlorophyll b with 600L of dimethyl sulfoxide, adding into 600L of activating solution, stirring at 25 ℃ under dark condition for 5h, then adding 12000L of chitosan solution, continuously stirring for 24h, transferring the reaction solution into a dialysis bag with molecular retention of 14000Da, dialyzing and purifying with deionized water for 4 days, freeze-drying the dialysed and purified liquid, and pulverizing to obtain chlorophyll grafted chitosan powder.
Step four: 15kg of triton X-100 serving as an emulsifier and 3000L of deionized water are stirred and mixed, 2500L of refined quinol xylene solution with the mass fraction of 10% and 40kg of solid paraffin are added, stirring is carried out for 3 hours at 80 ℃ and 2000r/min, and cooling is carried out, thus obtaining refined quinol emulsion.
Step five: dissolving 1.5kg of chlorophyll grafted chitosan powder with 60L of acetic acid solution with the mass fraction of 1% under the light-shielding condition, then adding 60L of refined quinoline emulsion, stirring and reacting for 14h under the light-shielding condition at 60 ℃, cooling and filtering, washing with deionized water for 3 times, and drying to obtain the chitosan coated refined quinoline microcapsule.
Step six: 2kg of chitosan coated refined quince microcapsules, 0.8kg of acifluorfen, 2kg of bentazone, 2kg of polyether modified silicone oil, 0.08kg of p-hydroxybenzoic acid, 0.4kg of triamcinolone acetonide X-750, 0.3kg of hydroxyethyl cellulose, 0.2kg of polyvinyl alcohol and 6kg of deionized water are added into a stirrer, and stirred for 20min under the conditions of 1500r/min and light shielding, so as to obtain the herbicide containing refined quince, acifluorfen and bentazone.
Comparative example 1: based on example 3, unmodified chitosan is directly used for replacing chlorophyll grafted chitosan powder in the fifth step to prepare an unmodified chitosan coated refined quince microcapsule, and the unmodified chitosan coated refined quince microcapsule is applied to the subsequent step to prepare the herbicide containing refined quince, acifluorfen and bentazone.
Comparative example 2: on the basis of example 3, no parahydroxybenzoic acid was added, and the remaining steps remained unchanged, to prepare a herbicide containing mequindox, acifluorfen and bentazone.
Comparative example 3: referring to the prior art, 2kg of bentazone, 2kg of quizalofop-p-ethyl, 0.8kg of acifluorfen, 0.7kg of sodium lignin sulfonate, 0.5kg of sodium dodecyl sulfate, 0.5kg of ammonium sulfate and 0.8kg of ammonium sulfate are uniformly mixed to prepare the herbicide containing the quizalofop-p-ethyl, the acifluorfen and the bentazone.
The chitosan-coated refined quinoline microcapsules prepared in example 3 and comparative example 2 were each weighed into 2 groups of 1g samples, then the samples were respectively added into flasks, respectively dispersed for 2 minutes with 20mL of acetone, the first group was dispersed under light conditions, the second group was dispersed under light-shielding conditions, the extract was collected by filtration and concentrated to 2mL with a dry nitrogen blower, and the refined quinoline content was detected with a gas chromatograph after filtration, and the results are shown in table 1:
TABLE 1
In example 3, the chitosan coated refined olaquindox microcapsule can release more refined olaquindox when dispersed under the illumination condition, and the surface of the chitosan coated refined olaquindox microcapsule has photocleavable property.
Test of efficacy of example 1-example 2 and comparative example 1-comparative example 3 different herbicides were diluted 100-fold with clear water and sprayed with an atomizer onto paddy fields uniformly grown with barnyard grass, 5 pieces of each group were selected with an area of 1m 2 The average numbers of barnyard grass and rice seedlings were counted, and after 20 days, the control effect on barnyard grass ((initial number-20 days later)/initial number) was calculated, and the results are shown in table 1:
TABLE 1
As can be seen from Table 1, the herbicides of examples 1 to 3 have the best control effect on barnyard grass. The worst effect in comparative example 1 is that English unmodified chitosan is inconvenient to release coated refined olaquindox, and the worse effect in comparative example 2 is that the chitosan coated refined olaquindox microcapsule is broken in advance to release the content due to the fact that the hydroxy benzoic acid with light stabilization effect is not added.
It should be noted that in this document, terms such as "comprises," "comprising," or any other variation thereof, are intended to cover a non-exclusive inclusion, such that a process, method, article, or apparatus that comprises a list of elements does not include only those elements but may include other elements not expressly listed or inherent to such process, method, article, or apparatus.
Although embodiments of the present invention have been shown and described, it will be understood by those skilled in the art that various changes, modifications, substitutions and alterations can be made therein without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (10)
1. The herbicide containing the mequindox, the acifluorfen and the bentazone is characterized by comprising the following components in parts by mass:
15-20 parts of chitosan coated refined olaquindox microcapsule, 4-8 parts of acifluorfen, 15-20 parts of bentazone, 15-20 parts of polyether modified silicone oil, 0.2-0.8 part of parahydroxybenzoic acid, 2-4 parts of anionic emulsifier, 2-3 parts of hydroxyethyl cellulose, 1-2 parts of polyvinyl alcohol and 40-60 parts of deionized water;
the chitosan coated refined olaquindox microcapsule is prepared through the following steps:
mixing and stirring triton X-100 and deionized water, adding refined olaquindox solution with the mass fraction of 10% and solid paraffin, stirring for 2-3h at 75-80 ℃ and 1500-2000r/min, and cooling to obtain refined olaquindox emulsion;
dissolving chlorophyll grafted chitosan powder in acetic acid solution with mass fraction of 1% under light-shielding condition, adding refined olaquindox emulsion, stirring at 60deg.C under light-shielding condition for reaction for 12-14 hr, cooling, filtering, washing with deionized water for 2-3 times, and drying to obtain chitosan coated refined olaquindox microcapsule.
2. The herbicide containing mequindox, acifluorfen and bentazone according to claim 1, wherein the dosage ratio of the triamcinolone acetonide X-100, deionized water, the mequindox solution and the solid paraffin is 0.1-0.15g:20-30mL:20-25mL:0.3-0.4g.
3. The herbicide containing mequindox, acifluorfen and bentazone according to claim 1, characterized in that the dosage ratio of chlorophyll grafted chitosan powder, acetic acid solution and mequindox emulsion is 1-1.5g:50-60mL:50-60mL.
4. The herbicide containing mequindox, acifluorfen and bentazone according to claim 1, wherein the anionic emulsifier is triamcinolone X-200 or triamcinolone X-750.
5. The herbicide containing mequindox, acifluorfen and bentazone according to claim 1, characterized in that the green grafted chitosan powder is prepared by the following steps:
dissolving chlorophyll with dimethyl sulfoxide, adding into the activating solution, stirring at 20-25deg.C in dark for 4-5 hr, adding chitosan solution, stirring for 20-24 hr, transferring into dialysis bag with molecular retention of 10000-14000Da, dialyzing with deionized water for 2-4 days, lyophilizing, and pulverizing to obtain chlorophyll grafted chitosan powder.
6. The herbicide containing mequindox, acifluorfen and bentazone according to claim 5, characterized in that the dosage ratio of chlorophyll, dimethyl sulfoxide, activating solution and chitosan solution is 0.25-0.5g:50-60mL:50-60mL:1-1.2L.
7. The herbicide containing mequindox, acifluorfen and bentazone of claim 5, wherein the chlorophyll is chlorophyll a or chlorophyll b.
8. The herbicide containing mequindox, acifluorfen and bentazone of claim 5, wherein the most recent method of chitosan solution is: adding chitosan and acetic acid solution with mass fraction of 2-5% into a reaction kettle, stirring for 30-60min, and regulating pH value to 6+ -0.2 with sodium hydroxide solution to obtain chitosan solution; the dosage ratio of the chitosan to the acetic acid solution is 0.1-0.15g:100-120mL.
9. The herbicide containing mequindox, acifluorfen and bentazone according to claim 5, wherein the preparation method of the activating solution is as follows: regulating the pH value of a morpholine ethanesulfonic acid aqueous solution with the molar concentration of 10 mmo/L to 6+/-0.2 by using a sodium hydroxide solution with the mass fraction of 25%, then adding 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride and N-hydroxysuccinimide, stirring and dissolving to obtain an activated liquid; the dosage ratio of the morpholine ethanesulfonic acid aqueous solution, the 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride and the N-hydroxysuccinimide is 50-60mL:0.55g:0.66g.
10. The method for preparing the herbicide containing mequindox, acifluorfen and bentazone according to claim 1, which is characterized by comprising the following steps:
adding chitosan coated refined quince microcapsule, acifluorfen, bentazone, polyether modified silicone oil, parahydroxybenzoic acid, anionic emulsifier, hydroxyethyl cellulose, polyvinyl alcohol and deionized water into a stirrer, stirring for 15-20min under 1000-1500r/min and light-proof condition, and obtaining herbicide containing refined quince, acifluorfen and bentazone.
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