JP2024516932A - アルキルエステル塩誘導体及び調製法と応用 - Google Patents
アルキルエステル塩誘導体及び調製法と応用 Download PDFInfo
- Publication number
- JP2024516932A JP2024516932A JP2023559019A JP2023559019A JP2024516932A JP 2024516932 A JP2024516932 A JP 2024516932A JP 2023559019 A JP2023559019 A JP 2023559019A JP 2023559019 A JP2023559019 A JP 2023559019A JP 2024516932 A JP2024516932 A JP 2024516932A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl ester
- salt derivative
- ester salt
- acid
- hydroxyethylethylenediamine
- 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.)
- Pending
Links
- 125000005907 alkyl ester group Chemical group 0.000 title claims abstract description 48
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000126 substance Substances 0.000 claims abstract description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims abstract description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims abstract description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 claims abstract description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 40
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 36
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 claims description 35
- 239000004593 Epoxy Substances 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 24
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 23
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 22
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 20
- 235000019253 formic acid Nutrition 0.000 claims description 20
- 150000007522 mineralic acids Chemical class 0.000 claims description 18
- 150000002148 esters Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 239000002994 raw material Substances 0.000 claims description 15
- 239000000463 material Substances 0.000 claims description 14
- 239000005562 Glyphosate Substances 0.000 claims description 13
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims description 13
- 229940097068 glyphosate Drugs 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 239000011787 zinc oxide Substances 0.000 claims description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 10
- 238000006735 epoxidation reaction Methods 0.000 claims description 10
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 10
- 235000012424 soybean oil Nutrition 0.000 claims description 9
- 239000003549 soybean oil Substances 0.000 claims description 9
- -1 fatty acid isopropyl ester Chemical class 0.000 claims description 8
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 6
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 claims description 6
- 239000000194 fatty acid Substances 0.000 claims description 6
- 229930195729 fatty acid Natural products 0.000 claims description 6
- 230000002363 herbicidal effect Effects 0.000 claims description 6
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 claims description 6
- 229940073769 methyl oleate Drugs 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 5
- 239000004009 herbicide Substances 0.000 claims description 5
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims description 4
- 235000019387 fatty acid methyl ester Nutrition 0.000 claims description 3
- 150000004702 methyl esters Chemical class 0.000 claims description 3
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004494 ethyl ester group Chemical group 0.000 claims description 2
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 claims description 2
- 229940093471 ethyl oleate Drugs 0.000 claims description 2
- 150000004665 fatty acids Chemical class 0.000 claims description 2
- WIBFFTLQMKKBLZ-SEYXRHQNSA-N n-butyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCCC WIBFFTLQMKKBLZ-SEYXRHQNSA-N 0.000 claims description 2
- PZQSQRCNMZGWFT-QXMHVHEDSA-N propan-2-yl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC(C)C PZQSQRCNMZGWFT-QXMHVHEDSA-N 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 11
- 238000001179 sorption measurement Methods 0.000 abstract description 4
- 239000007864 aqueous solution Substances 0.000 abstract description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 15
- 241000196324 Embryophyta Species 0.000 description 9
- 239000006227 byproduct Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 238000004821 distillation Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000003814 drug Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 4
- 150000003944 halohydrins Chemical class 0.000 description 4
- 150000004965 peroxy acids Chemical class 0.000 description 4
- 239000003760 tallow Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 238000007142 ring opening reaction Methods 0.000 description 3
- 239000012958 Amine synergist Substances 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- VUSHVKUNOXWQTG-KHPPLWFESA-N methyl (Z)-2-oxooctadec-9-enoate Chemical compound O=C(C(=O)OC)CCCCCC\C=C/CCCCCCCC VUSHVKUNOXWQTG-KHPPLWFESA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 240000000321 Abutilon grandifolium Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 235000003403 Limnocharis flava Nutrition 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- ZEKANFGSDXODPD-UHFFFAOYSA-N glyphosate-isopropylammonium Chemical compound CC(C)N.OC(=O)CNCP(O)(O)=O ZEKANFGSDXODPD-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000000622 irritating effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/22—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated the carbon skeleton being further substituted by oxygen atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
-
- 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
- A01N25/30—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 characterised by the surfactants
-
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Dispersion Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202110359364.9A CN112794805B (zh) | 2021-04-02 | 2021-04-02 | 一种烷基酯基盐衍生物、其制备方法和应用 |
CN202110359364.9 | 2021-04-02 | ||
PCT/CN2021/114507 WO2022205753A1 (zh) | 2021-04-02 | 2021-08-25 | 一种烷基酯基盐衍生物、其制备方法和应用 |
Publications (1)
Publication Number | Publication Date |
---|---|
JP2024516932A true JP2024516932A (ja) | 2024-04-18 |
Family
ID=75816137
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2023559019A Pending JP2024516932A (ja) | 2021-04-02 | 2021-08-25 | アルキルエステル塩誘導体及び調製法と応用 |
Country Status (3)
Country | Link |
---|---|
JP (1) | JP2024516932A (zh) |
CN (1) | CN112794805B (zh) |
WO (1) | WO2022205753A1 (zh) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112794805B (zh) * | 2021-04-02 | 2021-06-22 | 苏州丰倍生物科技有限公司 | 一种烷基酯基盐衍生物、其制备方法和应用 |
Family Cites Families (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5563111A (en) * | 1993-08-03 | 1996-10-08 | Kao Corporation | Agricultural chemical composition comprising amine surfactants with at least one ester or amide linkage |
EP0685995B1 (en) * | 1993-12-28 | 1999-07-14 | Kao Corporation | Enhancer composition for agricultural chemicals and agricultural chemical composition |
US5783516A (en) * | 1996-06-28 | 1998-07-21 | Albemarle Corporation | Herbicidal and plant growth regulant compositions and their use |
FR2765075B1 (fr) * | 1997-06-27 | 2003-08-15 | Flamel Tech Sa | Emulsion de glyphosate, l'un de ses procedes de preparation et composition phytotoxique en contenant |
NZ502397A (en) * | 1997-07-22 | 2002-04-26 | Monsanto Co | Storage stable high-loaded ammonium glyphosate and surfactant formulations |
US7135437B2 (en) * | 2000-05-19 | 2006-11-14 | Monsanto Technology Llc | Stable liquid pesticide compositions |
US6503869B1 (en) * | 2000-08-21 | 2003-01-07 | Falcon Lab Llc | Enhanced post-emergent herbicidal compositions containing ammonium salts and methods of using the same |
IT1395312B1 (it) * | 2009-08-10 | 2012-09-05 | Trentino Sviluppo Spa | Composizione per il trattamento e/o la profilassi di piante. |
CN101648121B (zh) * | 2009-08-21 | 2012-08-29 | 江苏钟山化工有限公司 | 一种水溶性增稠剂及其制法和在农药制剂中的应用 |
EP3111764B1 (en) * | 2010-09-15 | 2019-10-23 | Dow AgroSciences LLC | Amine surfactants for controlling herbicide spray drift |
PL226607B1 (pl) * | 2013-04-19 | 2017-08-31 | Inst Ciężkiej Syntezy Organicznej Blachownia | Kompozycja herbicydowa |
US20160015033A1 (en) * | 2014-07-21 | 2016-01-21 | Dow Agrosciences Llc | Compounds derived from herbicidal carboxylic acids and tetraalkylammonium or (arylalkyl)trialkylammonium hydroxides |
CN104814008B (zh) * | 2015-03-25 | 2016-06-15 | 深圳市长园嘉彩环境材料有限公司 | 一种草甘膦铵盐专用增稠增效助剂 |
JP6242844B2 (ja) * | 2015-10-01 | 2017-12-06 | 花王株式会社 | アミノ酸系農薬用効力増強剤組成物 |
CN109310095A (zh) * | 2016-05-11 | 2019-02-05 | 孟山都技术公司 | 含酰胺基烷基胺表面活性剂的草甘膦制剂 |
WO2021007683A1 (en) * | 2019-07-12 | 2021-01-21 | Rhodia Operations | Stable herbicidal compositions comprising amine oxide and betaine |
CN110818577B (zh) * | 2019-11-07 | 2022-12-06 | 南京威尔生物化学有限公司 | 一种高药效草甘膦颗粒剂助剂的制备方法和应用 |
CN112794854A (zh) * | 2019-11-14 | 2021-05-14 | 苏州科睿思制药有限公司 | Ribociclib的半琥珀酸盐晶型CSI及其制备方法和用途 |
CN111066810A (zh) * | 2019-12-27 | 2020-04-28 | 中国农业科学院棉花研究所 | 草甘膦复配组合物及其制备方法与除草剂 |
CN112794805B (zh) * | 2021-04-02 | 2021-06-22 | 苏州丰倍生物科技有限公司 | 一种烷基酯基盐衍生物、其制备方法和应用 |
-
2021
- 2021-04-02 CN CN202110359364.9A patent/CN112794805B/zh active Active
- 2021-08-25 WO PCT/CN2021/114507 patent/WO2022205753A1/zh active Application Filing
- 2021-08-25 JP JP2023559019A patent/JP2024516932A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
CN112794805A (zh) | 2021-05-14 |
WO2022205753A1 (zh) | 2022-10-06 |
CN112794805B (zh) | 2021-06-22 |
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