CN115943956A - Bromodifenoxanil dispersible oil suspending agent and preparation method thereof - Google Patents
Bromodifenoxanil dispersible oil suspending agent and preparation method thereof Download PDFInfo
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- CN115943956A CN115943956A CN202211152571.8A CN202211152571A CN115943956A CN 115943956 A CN115943956 A CN 115943956A CN 202211152571 A CN202211152571 A CN 202211152571A CN 115943956 A CN115943956 A CN 115943956A
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- polyoxyethylene ether
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- 239000000375 suspending agent Substances 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 18
- 239000002562 thickening agent Substances 0.000 claims abstract description 12
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229940051841 polyoxyethylene ether Drugs 0.000 claims description 50
- 229920000056 polyoxyethylene ether Polymers 0.000 claims description 50
- 239000003921 oil Substances 0.000 claims description 20
- 235000019198 oils Nutrition 0.000 claims description 20
- 239000004359 castor oil Substances 0.000 claims description 18
- 235000019438 castor oil Nutrition 0.000 claims description 18
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 18
- AMWBKZHMFJEZRP-UHFFFAOYSA-N 3-fluorobenzene-1,2-dicarboxamide Chemical compound NC(=O)C1=CC=CC(F)=C1C(N)=O AMWBKZHMFJEZRP-UHFFFAOYSA-N 0.000 claims description 17
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 claims description 12
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 claims description 11
- 150000002191 fatty alcohols Chemical class 0.000 claims description 10
- 239000012053 oil suspension Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 239000000440 bentonite Substances 0.000 claims description 6
- 229910000278 bentonite Inorganic materials 0.000 claims description 6
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 5
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 claims description 5
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 claims description 5
- 229940073769 methyl oleate Drugs 0.000 claims description 5
- -1 sorbitan fatty acid ester Chemical class 0.000 claims description 5
- DMAXMXPDVWTIRV-UHFFFAOYSA-N 2-(2-phenylethyl)phenol Chemical compound OC1=CC=CC=C1CCC1=CC=CC=C1 DMAXMXPDVWTIRV-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 239000003549 soybean oil Substances 0.000 claims description 4
- 235000012424 soybean oil Nutrition 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- 239000004576 sand Substances 0.000 claims description 3
- 238000010008 shearing Methods 0.000 claims description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 claims description 2
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 2
- 239000004113 Sepiolite Substances 0.000 claims description 2
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- CWFOCCVIPCEQCK-UHFFFAOYSA-N chlorfenapyr Chemical compound BrC1=C(C(F)(F)F)N(COCC)C(C=2C=CC(Cl)=CC=2)=C1C#N CWFOCCVIPCEQCK-UHFFFAOYSA-N 0.000 claims description 2
- 235000005687 corn oil Nutrition 0.000 claims description 2
- 239000002285 corn oil Substances 0.000 claims description 2
- 235000012343 cottonseed oil Nutrition 0.000 claims description 2
- 239000002385 cottonseed oil Substances 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- 229910021485 fumed silica Inorganic materials 0.000 claims description 2
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 claims description 2
- 229920001451 polypropylene glycol Polymers 0.000 claims description 2
- 229920000136 polysorbate Polymers 0.000 claims description 2
- 229950008882 polysorbate Drugs 0.000 claims description 2
- 229910052624 sepiolite Inorganic materials 0.000 claims description 2
- 235000019355 sepiolite Nutrition 0.000 claims description 2
- 229940100515 sorbitan Drugs 0.000 claims description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 4
- 241000982106 Brevicoryne Species 0.000 claims 2
- CTHMWRJVVKCPDA-UHFFFAOYSA-N 3-bromobenzene-1,2-dicarboxamide Chemical compound NC(=O)C1=CC=CC(Br)=C1C(N)=O CTHMWRJVVKCPDA-UHFFFAOYSA-N 0.000 claims 1
- 241000186146 Brevibacterium Species 0.000 claims 1
- 239000012141 concentrate Substances 0.000 claims 1
- 235000010446 mineral oil Nutrition 0.000 claims 1
- 239000002480 mineral oil Substances 0.000 claims 1
- 241000607479 Yersinia pestis Species 0.000 abstract description 13
- 230000002195 synergetic effect Effects 0.000 abstract description 6
- 241000254173 Coleoptera Species 0.000 abstract description 5
- 241000258937 Hemiptera Species 0.000 abstract description 3
- 241000255777 Lepidoptera Species 0.000 abstract description 3
- 206010059866 Drug resistance Diseases 0.000 abstract description 2
- 231100000053 low toxicity Toxicity 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- 241000238631 Hexapoda Species 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 241000500437 Plutella xylostella Species 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000010413 mother solution Substances 0.000 description 4
- 230000009471 action Effects 0.000 description 3
- 230000000749 insecticidal effect Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000575 pesticide Substances 0.000 description 3
- OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 description 2
- WXYAXNJJSMYZGM-UHFFFAOYSA-N 3-formamidobenzamide Chemical compound NC(=O)C1=CC=CC(NC=O)=C1 WXYAXNJJSMYZGM-UHFFFAOYSA-N 0.000 description 2
- 241001674044 Blattodea Species 0.000 description 2
- 241000255925 Diptera Species 0.000 description 2
- 241000257303 Hymenoptera Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000256602 Isoptera Species 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 230000001055 chewing effect Effects 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 231100000518 lethal Toxicity 0.000 description 2
- 230000001665 lethal effect Effects 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 238000002791 soaking Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 230000001018 virulence Effects 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- KGGHWIKBOIQEAJ-UHFFFAOYSA-N 2-fluorobenzamide Chemical compound NC(=O)C1=CC=CC=C1F KGGHWIKBOIQEAJ-UHFFFAOYSA-N 0.000 description 1
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000005489 Bromoxynil Substances 0.000 description 1
- 239000005886 Chlorantraniliprole Substances 0.000 description 1
- 108010062745 Chloride Channels Proteins 0.000 description 1
- 102000011045 Chloride Channels Human genes 0.000 description 1
- 241001414989 Thysanoptera Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229940125516 allosteric modulator Drugs 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 238000010009 beating Methods 0.000 description 1
- QSLZKWPYTWEWHC-UHFFFAOYSA-N broflanilide Chemical compound C=1C=CC(C(=O)NC=2C(=CC(=CC=2Br)C(F)(C(F)(F)F)C(F)(F)F)C(F)(F)F)=C(F)C=1N(C)C(=O)C1=CC=CC=C1 QSLZKWPYTWEWHC-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- PSOVNZZNOMJUBI-UHFFFAOYSA-N chlorantraniliprole Chemical compound CNC(=O)C1=CC(Cl)=CC(C)=C1NC(=O)C1=CC(Br)=NN1C1=NC=CC=C1Cl PSOVNZZNOMJUBI-UHFFFAOYSA-N 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008233 hard water Substances 0.000 description 1
- 238000005338 heat storage Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000012865 response to insecticide Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
Classifications
-
- 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
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention relates to the field of A01N43, in particular to a brotrochan difluoride dispersible oil suspending agent and a preparation method thereof, wherein the brotrochan difluoride dispersible oil suspending agent comprises, by weight, 5-60 parts of brotrochan difluoride, 0.5-3 parts of a thickening agent, 10-30 parts of an emulsifier and 10-80 parts of a dispersing carrier. The best synergistic effect can be generated by introducing the brotroche diamide and the compound shown in the formula (I) or the formula (II), the brotroche diamide and the compound shown in the formula (I) or the formula (II) have obviously improved co-toxicity coefficient, and the problem of drug resistance of pests is effectively solved. Can effectively control common pests such as homoptera, lepidoptera, coleoptera and the like, has the characteristics of high efficiency, low toxicity and low residue, and provides a new choice for controlling agricultural pests.
Description
Technical Field
The invention relates to the field of A01N43, in particular to a bromofenoxanil fluorobenzene bisamide dispersible oil suspending agent and a preparation method thereof.
Background
Brofenamid fluorobenzenediamide (broflanilide): the m-formamidobenzamide pesticide has excellent effect on controlling various chewing mouthparts pests such as caterpillars, beetles and the like, can be applied to special and row crops, and can prevent and control termites, ants, cockroaches and flies in non-crop areas. Bromoidal fluorobenzamide is an m-diamide (m-formamidobenzamide) insecticide developed by Mitsui chemistry and Pasteur together. The action mechanism of the compound is obviously different from the prior o-diamide insecticides such as chlorantraniliprole, and the like, and the compound is an allosteric modulator of a gamma-aminobutyric acid (GABA) gated chloride ion channel. The international commission on insecticide resistance action has classified it into 30 groups (IRAC Group 30), which are currently the only members of this Group. The bromoxynil fluorobenzdiamide has excellent effects on controlling various chewing mouthpart pests such as caterpillars and beetles, and can be applied to special and row crops and used for preventing and controlling termites, ants, cockroaches and flies in non-crop areas. For example, chinese application CN109757495A discloses a pesticide composition containing butynitrile and brotrochan difluoride, specifically, butynitrile and brotrochan difluoride are used as core drug components, the composition can generate a synergistic effect, and has excellent control effects on homoptera pests, lepidoptera pests, thysanoptera pests, coleoptera pests and other pests, but because the common application of butynitrile and brotrochan difluoride can amplify drug resistance genes of insect populations, and the resistance to butynitrile and brotrochan difluoride causes pesticide failure.
Disclosure of Invention
In order to solve the problems, the invention provides a dispersible oil suspending agent of the chlorfenapyr fluorobenzene diamide, which at least comprises the following preparation raw materials in parts by weight: 5-60 parts of bromofenoxanil and 5-60 parts of an effective component A, wherein the effective component A is selected from at least one of the compounds shown in the formulas (I) and (II):
a compound of the formula (I),
a compound of the formula (II),
as a preferable technical scheme, the dispersible oil suspending agent also comprises 0.5-3 parts of thickening agent, 10-30 parts of emulsifier and 10-80 parts of dispersing carrier by weight.
As a preferable technical scheme, the effective component A is a compound shown in a formula (I) or a compound shown in a formula (II).
As a preferred technical scheme, the mass ratio of the brotrochar benserdiamide to the compound shown in the formula (I) or the formula (II) is (40-1): (1-40), preferably (20-1): (1-20); further preferably, the mass ratio of the brofenpyrad to the compound shown in the formula (I) or the formula (II) is (4-1): (1-4), preferably (2-1): (1-2);
based on the system, the mass ratio of the introduced brotroche bendiamide to the compound shown in the formula (I) or the formula (II) is (2-1): the inventor analyzes that the reason why the brotrochan fluorobenzene bisamide has an insecticidal effect by matching with the compound shown in the formula (I) or the compound shown in the formula (II) through different insecticidal mechanisms, the action range is wider, the insecticidal effect is improved, and multi-point effects on common pest control are achieved.
As a preferable technical scheme, the emulsifier is one or more of castor oil polyoxyethylene ether, phenethyl phenol polyoxyethylene ether, calcium dodecyl benzene sulfonate, polysorbate, sorbitan fatty acid ester, phenethyl phenol polyoxypropylene ether, nonylphenol polyoxyethylene ether, alkylphenol polyoxyethylene ether, fatty alcohol polyoxyethylene ether, polyoxyethylene ether carboxylate, polyoxyethylene ether, alkylphenol polyoxyethylene ether sulfosuccinate and castor oil ethylene oxide addition product. Preferably, the emulsifier is a combination of castor oil polyoxyethylene ether, fatty alcohol polyoxyethylene ether, calcium dodecylbenzene sulfonate and alkylphenol polyoxyethylene ether sulfosuccinate. Preferably, the mass ratio of the castor oil polyoxyethylene ether, the fatty alcohol polyoxyethylene ether, the calcium dodecylbenzene sulfonate and the alkylphenol polyoxyethylene ether sulfosuccinate is (3-8): (2-6): (8-12): (1-6). Based on the bromofenoxanil, the compound shown in the formula (I) or the formula (II) adopted in the system, the mass ratio of the compound to the compound is (3-8): (2-6): (8-12): and (1) the castor oil polyoxyethylene ether, the fatty alcohol polyoxyethylene ether, the calcium dodecyl benzene sulfonate and the alkylphenol polyoxyethylene ether sulfosuccinate are used as the emulsifier, so that the provided dispersible oil suspending agent has long-term stable performance, good emulsifying dispersibility and good drug effect maintenance under the condition of higher or lower temperature, and the storage time of the product is prolonged.
As a preferable technical scheme, the HLB value of the castor oil polyoxyethylene ether is 9-14; preferably, the HLB value of the castor oil polyoxyethylene ether is 9-10, the mark is C875007, and the castor oil polyoxyethylene ether is obtained from Shanghai Maxin Biotechnology and science Co. The CAS number of the fatty alcohol-polyoxyethylene ether is 111-09-3, the product number is P35056, and the product is from Shanghai Dingfen chemical technology Co. The alkylphenol polyoxyethylene ether sulfosuccinate is DNS-1035 and is derived from HANERCHEM.
As a preferable technical scheme, the thickening agent is one or more of organic bentonite, fumed silica, magnesium aluminum silicate and sepiolite; preferably, the thickener is organic bentonite, and is derived from Zhejiang Fenghong New materials GmbH. Based on the system, the organic bentonite is introduced as the thickening agent, so that the anti-settling effect in the system is better, and the suspension stability of the dispersible oil suspending agent is effectively improved. This is probably because the organobentonite is dispersed in the methyl oleate into a network structure, and effectively prevents the bromofenoxanil, the compound of formula (I) or formula (II) from sinking, and avoids the generation of hard precipitate.
As a preferred technical scheme, the dispersion carrier is at least one of methyl oleate, soybean oil, epoxidized soybean oil, corn oil, rapeseed oil and cottonseed oil; preferably, the dispersing vehicle is methyl oleate.
The invention also provides a preparation method of the brevibra fluorobenzene bisamide dispersible oil suspending agent, which comprises the steps of mixing the brevibra fluorobenzene bisamide, the effective component A, the thickening agent, the emulsifying agent and the dispersing carrier according to parts by weight, shearing, and sanding by a sand mill to obtain the brevibra fluorobenzene bisamide dispersible oil suspending agent.
Has the advantages that:
1. the invention provides a brotrochan difluoride dispersible oil suspending agent and a preparation method thereof.
2. Based on the bromofenoxanil, the compound shown in the formula (I) or the formula (II) adopted in the system, the mass ratio of the compound to the compound is (3-8): (2-6): (8-12): and (1-6) the castor oil polyoxyethylene ether, the fatty alcohol polyoxyethylene ether, the calcium dodecyl benzene sulfonate and the alkylphenol polyoxyethylene ether sulfosuccinate are used as emulsifiers, so that the provided dispersible oil suspending agent has long-term stable performance, good emulsifying dispersibility and good efficacy maintenance under the condition of higher or lower temperature, and the storage time of the product is prolonged.
3. Based on the system, the organic bentonite is introduced into the system as the thickening agent, so that the anti-settling effect in the system is better, and the suspension stability of the dispersible oil suspending agent is effectively improved.
4. The bromine insect fluorobenzene bisamide dispersible oil suspending agent provided by the invention can effectively control common pests such as homoptera, lepidoptera, coleoptera and the like, has the characteristics of high efficiency, low toxicity and low residue, and provides a new choice for controlling agricultural pests.
Detailed Description
Examples 1 to 13
In one aspect, embodiments 1-13 of the present invention provide a dispersible oil suspension of bromofenoxanil and fluorobenzene bisamide, and the raw material formula is shown in table 1 in parts by weight.
TABLE 1,
The effective component A is a compound shown in a formula (I), wherein the structure of the compound shown in the formula (I) is as follows:
the emulsifier is the combination of castor oil polyoxyethylene ether, fatty alcohol polyoxyethylene ether, calcium dodecyl benzene sulfonate and alkylphenol polyoxyethylene ether sulfosuccinate. The mass ratio of the castor oil polyoxyethylene ether to the fatty alcohol polyoxyethylene ether to the calcium dodecyl benzene sulfonate to the alkylphenol polyoxyethylene ether sulfosuccinate is 6:5:9:4. the HLB value of the castor oil polyoxyethylene ether is 9-10, the mark is C875007, and the castor oil polyoxyethylene ether is from Shanghai Michelin Biotech limited. The CAS number of the fatty alcohol-polyoxyethylene ether is 111-09-3, the product number is P35056, and the product is from Shanghai Dingfen chemical technology Co. The alkylphenol polyoxyethylene ether sulfosuccinate is DNS-1035 and is derived from HANERCHEM.
The thickener is organic bentonite and is derived from Zhejiang Fenghong new material GmbH.
The dispersing carrier is methyl oleate.
In another aspect, embodiments 1-13 of the present invention provide a method for preparing a bregma fluorobenzene bisamide dispersible oil suspension, which comprises mixing, by weight, bregma fluorobenzene bisamide, a compound of formula (I), a thickener, an emulsifier, and a dispersing carrier, shearing for 30min, and sanding for 60min with a sand mill.
Examples 14 to 26
Examples 14 to 26 of the present invention provide a bromofenoxanil dispersible oil suspension and a preparation method thereof, and the specific implementation modes are the same as examples 1 to 13, respectively. Except that the compound of formula (I) is replaced with a compound of formula (II) having the structure:
comparative example 1
The embodiment of the invention is the same as that of example 5, except that the emulsifier is calcium dodecyl benzene sulfonate.
Comparative example 2
Comparative example 2 of the present invention provides a bromofenoxanil-fluorobenzenediamide dispersible oil suspension and a preparation method thereof, and the specific implementation manner is the same as example 5 except that the dispersion carrier is isopropanol.
Performance test method
1. Dispersion stability:
measured according to the CIPAC MT180 method, diluted with standard hard water at 30 ℃ and meeting the following requirements:
time stability limit after dispersion
The dispersion property is recorded as "pass"; otherwise, the test is recorded as "fail".
2. Heat storage stability: the water dispersible oil suspension of bromofenoxanil prepared in examples and comparative examples was sealed in a 50mL glass bottle, stored in an incubator at 54 ℃ ± 2 ℃ for 14 days, taken out, placed in a desiccator, cooled to room temperature, and the effective ingredients before and after thermal storage of the product were determined: contents of the compound (A1) of the formula (I), the compound (A2) of the formula (II) and the bromofenoxanil (B), and a content change rate of the effective ingredient was calculated by the following formula.
The rate of change in the content of active ingredient = (the content of active ingredient before hot storage-the content of active ingredient after hot storage)/the content of active ingredient before hot storage × 100%.
TABLE 2,
3. And (3) determining the cotoxicity coefficient of the compound shown in the formula (I) or the compound shown in the formula (II) and the brotrochan difluoride to the plutella xylostella in different proportions.
The specific test method comprises the following steps:
adopting a leaf soaking method: according to the results of the preliminary test,
accurately weighing 0.2062g of 97% original drug of the compound shown in the formula (I) or 97% original drug of the compound shown in the formula (II) and dissolving the 97% original drug of the compound shown in the formula (I) by 0.5mL of mixed solution, adding 0.2mL of emulsifier Twenen 80, stirring the mixture evenly, adding 99.3mL of clear water to prepare a mother solution of 2000mg/L, diluting the mother solution into 1000, 500, 250, 125 and 62.5mg/L by 2 times of water containing the emulsifier of 0.1 percent Twen 80, and carrying out the test at 6 concentrations in total.
Accurately weighing 0.0102g of 98% technical product of the brevibramole fluorobenzene bisamide, dissolving the technical product by 0.5mL of DMF, adding 0.2ml of Tween80 emulsifier, uniformly stirring, adding 99.3mL of clear water to prepare a mother solution of 100mg/L, adding 10mL of the mother solution into 90mL of water containing 0.1% Tween80 emulsifier to prepare a test solution of 10mg/L, diluting the test solution into 5, 2.5, 1.25, 0.625 and 0.3125mg/L according to 2 times of proportion, and carrying out tests in 6 concentrations.
Preparing the compound shown in the formula (I) or the compound shown in the formula (II) and bromofenoxanil according to the proportion shown in the tables 3 and 4 to obtain a test liquid.
Beating cabbage leaves into leaf disks by using a puncher with the diameter of 18mm, soaking the liquid disks in test liquid medicine for 10s, putting the liquid disks into culture dishes (with the diameter of 90 mm) filled with moisturizing filter paper, putting 5 leaf disks into each dish, naturally drying, selecting 3-year-old diamondback moth larvae starved for 4h into the culture dishes, repeating the steps for 15 times, covering the dishes with a dish cover, culturing in a incubator under the conditions that the temperature is 25 +/-1 ℃ and the humidity is 60-80%, and the illumination L is D = 18h. And (5) checking the death condition of the test insects after 72h, and taking the test insects as dead insects if the test insects are lightly contacted with tweezers and do not respond. And (3) carrying out statistical processing on the data obtained by the test by using SPSS software to obtain a toxicity regression equation, lethal medium concentration, correlation coefficient and the like, and solving a cotoxicity coefficient (CTC) by using a Sun cloud Peel method. The judgment standard of the synergistic effect of the two effective components after compounding is as follows:
when CTC is greater than 120, it is synergistic, when CTC is less than 80, it is antagonistic, and when CTC is 80-120, it is additive.
The lethal middle concentration, the toxicity regression equation, the correlation coefficient and the cotoxicity coefficient of the compound shown in the formula (I) or the compound shown in the formula (II) and the bromoantraniliprole in each proportion to the plutella xylostella are shown in tables 3 and 4.
Table 3 shows indoor toxicity test results of the compound (a) of the formula (I) and the bromofenoxanil (B) at different ratios against plutella xylostella.
| Proportioning | Regression equation of virulence | Coefficient of correlation | LC50(mg/L) | Co-toxicity coefficient |
| A:B＝40：1 | Y＝3.1952+1.2549X | 0.9958 | 27.4300(21.0698-35.7105) | 95.4263 |
| A:B＝20:1 | Y＝3.5507+1.1313X | 0.9864 | 19.1027(15.1237-24.1286) | 105.0233 |
| A:B＝8:1 | Y＝3.6517+1.3559X | 0.9873 | 9.8723(8.3975-11.6062) | 124.0371 |
| A:B＝4:1 | Y＝3.8017+11.5200X | 0.9782 | 6.1430(5.1960-7.2620) | 128.9808 |
| A:B＝2:1 | Y＝4.1567+1.4281X | 0.9749 | 3.8949(3.0952-4.9013) | 133.0077 |
| A:B＝1:1 | Y＝4.3641+1.4876X | 0.9724 | 2.6756(2.0133-3.5559) | 135.1437 |
| A:B＝1:2 | Y＝4.5007+1.4609X | 0.9701 | 2.1965(1.5847-3.0446) | 126.434 |
| A:B＝1:4 | Y＝4.6006+1.4331X | 0.9832 | 1.8996(1.3251-2.7234) | 123.3121 |
| A:B＝1:8 | Y＝4.6358+1.4876X | 0.9741 | 1.7572(1.2156-2.5401) | 120.7116 |
| A:B＝1:20 | Y＝4.5985+1.5342X | 0.9842 | 1.8268(1.2846-2.5978) | 108.7708 |
| A:B＝1:40 | Y＝4.5634+1.5496X | 0.9816 | 1.9131(1.3622-2.6868) | 101.5159 |
| A | Y＝2.8973+1.3263X | 0.9988 | 38.4902(28.1618-52.6065) | — |
| B | Y＝4.5723+1.5381X | 0.9805 | 1.8971(1.3455-2.6748) | — |
As can be seen from the data in the table, the brotroche bendiamide and the compound shown in formula (I) have a synergistic effect, and particularly, when the mass ratio of the brotroche bendiamide to the compound shown in formula (I) is 1.
Table 4 shows the results of determining the co-toxicity of the compound (a) of the formula (II) and the bromofenoxanil (B) against plutella xylostella at different ratios.
| Proportioning | Regression equation of virulence | Correlation coefficient | LC50 (mg/L) 95% confidence Limit | Co-toxicity coefficient |
| A:B＝40：1 | Y＝3.3638+1.1018X | 0.9963 | 30.5495(22.3428-41.7704) | 97.0129 |
| A:B＝20:1 | Y＝3.7531+0.9357X | 0.985 | 21.5109(16.0137-28.8952) | 117.3703 |
| A:B＝8:1 | Y＝3.9010+0.9479X | 0.9822 | 14.4346(11.3388-18.3756) | 124.5054 |
| A:B＝4:1 | Y＝3.8799+1.1417X | 0.9831 | 9.5734(7.9243-11.5658) | 133.7618 |
| A:B＝2:1 | Y＝4.0658+1.1397X | 0.9864 | 6.6027(5.3641-8.1274) | 135.5123 |
| A:B＝1:1 | Y＝4.1761+1.1748X | 0.9772 | 5.0277(3.9870-6.3401) | 129.2766 |
| A:B＝1:2 | Y＝4.2751+1.2022X | 0.9748 | 4.0086(3.0909-5.1986) | 127.3146 |
| A:B＝1:4 | Y＝4.2657+1.3591X | 0.979 | 3.4695(2.6820-4.4882) | 125.5247 |
| A:B＝1:8 | Y＝4.1836+1.5950X | 0.976 | 3.2499(2.5618-4.1227) | 122.0741 |
| A:B＝1:20 | Y＝3.9587+2.0200X | 0.9705 | 3.2772(2.6889-3.9941) | 113.8163 |
| A:B＝1:40 | Y＝3.8497+2.0927X | 0.9728 | 3.5454(2.9528-4.2596) | 102.9529 |
| A | Y＝2.9465+1.3169X | 0.9994 | 36.2554(26.7919-49.0614) | — |
| B | Y＝3.9382+1.9212X | 0.9815 | 3.3598(2.9386-4.3367) | — |
As can be seen from the data in the table, the brotroche bendiamide and the compound shown in formula (II) have a synergistic effect, and especially when the mass ratio of the compound shown in formula (II) to the brotroche bendiamide is 2.
Claims (10)
1. The water dispersible oil suspending agent of the chlorfenapyr fluorobenzene bisamide is characterized by comprising the following preparation raw materials in parts by weight: 5-60 parts of bromofenoxanil and 5-60 parts of an effective component A, wherein the effective component A is selected from at least one of the compounds shown in the formulas (I) and (II):
a compound of the formula (I),
a compound of the formula (II),
2. the brevibra fluorobenzene bisamide dispersible oil suspending agent according to claim 1, wherein the dispersible oil suspending agent further comprises 0.5-3 parts by weight of a thickening agent, 10-30 parts by weight of an emulsifier and 10-80 parts by weight of a dispersing carrier.
3. The dispersible oil suspension concentrate of brofentoo benzamide as claimed in claim 2, wherein the mass ratio of the brofentoo benzamide to the compound of formula (I) or formula (II) is 1: (0.025-40).
4. The bromobenzene bisamide dispersible oil suspending agent as claimed in claim 3, wherein as a preferable technical scheme, the emulsifier is one or more of castor oil polyoxyethylene ether, phenethyl phenol polyoxyethylene ether, calcium dodecyl benzene sulfonate, polysorbate, sorbitan fatty acid ester, phenethyl phenol polyoxypropylene ether, nonylphenol polyoxyethylene ether, alkylphenol polyoxyethylene ether, fatty alcohol polyoxyethylene ether, polyoxyethylene ether carboxylate, polyoxyethylene ether, alkylphenol polyoxyethylene ether sulfosuccinate and castor oil ethylene oxide addition product.
5. The brevibrass fluorobenzene bisamide dispersible oil suspending agent as claimed in claim 4, wherein the emulsifier is a combination of castor oil polyoxyethylene ether, fatty alcohol polyoxyethylene ether, calcium dodecyl benzene sulfonate and alkylphenol polyoxyethylene ether sulfosuccinate.
6. The brevicoryne bromide fluorobenzene bisamide dispersible oil suspending agent as claimed in claim 5, wherein the mass ratio of the castor oil polyoxyethylene ether to the fatty alcohol polyoxyethylene ether to the calcium dodecylbenzene sulfonate to the alkylphenol polyoxyethylene ether sulfosuccinate is (3-8): (2-6): (8-12): (1-6).
7. The brevibrama fluorobenzene bisamide dispersible oil suspension as claimed in claim 5 or 6, wherein the HLB value of the castor oil polyoxyethylene ether is 9-14.
8. The water dispersible oil suspending agent of the brevicoryne difluoride as claimed in claim 7, wherein the thickener is one or more of organic bentonite, fumed silica, magnesium aluminum silicate and sepiolite.
9. The brevibacterium fluorobenzene diamide dispersible oil suspension as claimed in claim 8, wherein the dispersing carrier is at least one of methyl oleate, soybean oil, epoxidized soybean oil, corn oil, rapeseed oil, cottonseed oil and mineral oil.
10. The preparation method of the bregma fluorobenzene bisamide dispersible oil suspending agent according to any one of claims 2 to 9, characterized by mixing the bregma fluorobenzene bisamide, the effective component A, the thickening agent, the emulsifying agent and the dispersing carrier according to parts by weight, shearing, and sanding by a sand mill.
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| US5151428A (en) * | 1990-05-24 | 1992-09-29 | Noriyasu Sakamoto | Pyridine derivatives and their compositions for the control of insect pests |
| JPH04364167A (en) * | 1990-05-24 | 1992-12-16 | Sumitomo Chem Co Ltd | Pyridine compound, its production, intermediate thereof and pest control agent containing the same as active ingredient |
| US5243087A (en) * | 1990-05-24 | 1993-09-07 | Sumitomo Chemical Company, Limited | Pyridine derivatives, their production processes and their compositions for the control of insect pests |
| CN109757495A (en) * | 2019-03-07 | 2019-05-17 | 湖南速博生物技术有限公司 | Composition pesticide containing butene-fipronil and bromine worm fluorobenzene bisamide |
| CN111518022A (en) * | 2019-02-02 | 2020-08-11 | 华东理工大学 | Aromatic (hetero) cyclic ether compound with insecticidal activity and preparation method and application thereof |
| CN114246186A (en) * | 2021-12-22 | 2022-03-29 | 天津市汉邦植物保护剂有限责任公司 | Dispersible oil suspending agent containing kojic acid and cyantraniliprole as well as preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5151428A (en) * | 1990-05-24 | 1992-09-29 | Noriyasu Sakamoto | Pyridine derivatives and their compositions for the control of insect pests |
| JPH04364167A (en) * | 1990-05-24 | 1992-12-16 | Sumitomo Chem Co Ltd | Pyridine compound, its production, intermediate thereof and pest control agent containing the same as active ingredient |
| US5243087A (en) * | 1990-05-24 | 1993-09-07 | Sumitomo Chemical Company, Limited | Pyridine derivatives, their production processes and their compositions for the control of insect pests |
| CN111518022A (en) * | 2019-02-02 | 2020-08-11 | 华东理工大学 | Aromatic (hetero) cyclic ether compound with insecticidal activity and preparation method and application thereof |
| CN109757495A (en) * | 2019-03-07 | 2019-05-17 | 湖南速博生物技术有限公司 | Composition pesticide containing butene-fipronil and bromine worm fluorobenzene bisamide |
| CN114246186A (en) * | 2021-12-22 | 2022-03-29 | 天津市汉邦植物保护剂有限责任公司 | Dispersible oil suspending agent containing kojic acid and cyantraniliprole as well as preparation method and application thereof |
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