CA1293974C - Preparation de sels d'alcanolamine a partir d'acide carboxylique d'herbicides - Google Patents
Preparation de sels d'alcanolamine a partir d'acide carboxylique d'herbicidesInfo
- Publication number
- CA1293974C CA1293974C CA000526348A CA526348A CA1293974C CA 1293974 C CA1293974 C CA 1293974C CA 000526348 A CA000526348 A CA 000526348A CA 526348 A CA526348 A CA 526348A CA 1293974 C CA1293974 C CA 1293974C
- Authority
- CA
- Canada
- Prior art keywords
- mixture
- diethanolamine
- alkanolamine
- herbicide
- weight
- 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.)
- Expired - Fee Related
Links
- 239000004009 herbicide Substances 0.000 title claims abstract description 55
- 150000003839 salts Chemical class 0.000 title claims abstract description 35
- 238000002360 preparation method Methods 0.000 title description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 73
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 57
- 239000000843 powder Substances 0.000 claims abstract description 43
- 238000000034 method Methods 0.000 claims abstract description 39
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 claims abstract description 27
- 238000003756 stirring Methods 0.000 claims abstract description 23
- 239000005595 Picloram Substances 0.000 claims abstract description 22
- NQQVFXUMIDALNH-UHFFFAOYSA-N picloram Chemical compound NC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl NQQVFXUMIDALNH-UHFFFAOYSA-N 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- HUBANNPOLNYSAD-UHFFFAOYSA-N clopyralid Chemical compound OC(=O)C1=NC(Cl)=CC=C1Cl HUBANNPOLNYSAD-UHFFFAOYSA-N 0.000 claims abstract description 17
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000005500 Clopyralid Substances 0.000 claims abstract description 14
- 239000005504 Dicamba Substances 0.000 claims abstract description 14
- 101000742062 Bos taurus Protein phosphatase 1G Proteins 0.000 claims abstract description 12
- 229960002939 metizoline Drugs 0.000 claims abstract description 12
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 claims abstract description 11
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000005627 Triclopyr Substances 0.000 claims abstract description 10
- 239000005574 MCPA Substances 0.000 claims abstract description 9
- 238000010792 warming Methods 0.000 claims abstract description 9
- NDNKHWUXXOFHTD-UHFFFAOYSA-N metizoline Chemical compound CC=1SC2=CC=CC=C2C=1CC1=NCCN1 NDNKHWUXXOFHTD-UHFFFAOYSA-N 0.000 claims abstract 6
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 52
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 18
- 238000002156 mixing Methods 0.000 claims description 17
- 239000007787 solid Substances 0.000 claims description 15
- 239000004094 surface-active agent Substances 0.000 claims description 14
- 239000003352 sequestering agent Substances 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 8
- 229940031098 ethanolamine Drugs 0.000 claims description 8
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 claims description 7
- -1 phenyl- Chemical group 0.000 claims description 7
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 claims description 6
- 239000000377 silicon dioxide Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 5
- 229940043276 diisopropanolamine Drugs 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 229940102253 isopropanolamine Drugs 0.000 claims description 4
- QEVGZEDELICMKH-UHFFFAOYSA-N Diglycolic acid Chemical compound OC(=O)COCC(O)=O QEVGZEDELICMKH-UHFFFAOYSA-N 0.000 claims description 3
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical group OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 3
- 229940043237 diethanolamine Drugs 0.000 claims description 3
- 229960004418 trolamine Drugs 0.000 claims description 3
- 229910021485 fumed silica Inorganic materials 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 6
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 claims 2
- ZTMKADLOSYKWCA-UHFFFAOYSA-N lenacil Chemical compound O=C1NC=2CCCC=2C(=O)N1C1CCCCC1 ZTMKADLOSYKWCA-UHFFFAOYSA-N 0.000 claims 2
- 239000002609 medium Substances 0.000 claims 2
- QDGIAPPCJRFVEK-UHFFFAOYSA-N (1-methylpiperidin-4-yl) 2,2-bis(4-chlorophenoxy)acetate Chemical compound C1CN(C)CCC1OC(=O)C(OC=1C=CC(Cl)=CC=1)OC1=CC=C(Cl)C=C1 QDGIAPPCJRFVEK-UHFFFAOYSA-N 0.000 claims 1
- QPUYECUOLPXSFR-UHFFFAOYSA-N alpha-methyl-naphthalene Natural products C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 claims 1
- 239000003125 aqueous solvent Substances 0.000 abstract description 3
- 239000003960 organic solvent Substances 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 21
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 239000000155 melt Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 description 8
- HYJSGOXICXYZGS-UHFFFAOYSA-N benazolin Chemical compound C1=CC=C2SC(=O)N(CC(=O)O)C2=C1Cl HYJSGOXICXYZGS-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 241000196324 Embryophyta Species 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000001692 EU approved anti-caking agent Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000013066 combination product Substances 0.000 description 2
- 229940127555 combination product Drugs 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 239000003348 petrochemical agent Substances 0.000 description 2
- XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 description 1
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- IUQJDHJVPLLKFL-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)acetate;dimethylazanium Chemical compound CNC.OC(=O)COC1=CC=C(Cl)C=C1Cl IUQJDHJVPLLKFL-UHFFFAOYSA-N 0.000 description 1
- RHPUJHQBPORFGV-UHFFFAOYSA-N 4-chloro-2-methylphenol Chemical compound CC1=CC(Cl)=CC=C1O RHPUJHQBPORFGV-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 238000013494 PH determination Methods 0.000 description 1
- 235000018734 Sambucus australis Nutrition 0.000 description 1
- 244000180577 Sambucus australis Species 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000526348A CA1293974C (fr) | 1986-12-29 | 1986-12-29 | Preparation de sels d'alcanolamine a partir d'acide carboxylique d'herbicides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000526348A CA1293974C (fr) | 1986-12-29 | 1986-12-29 | Preparation de sels d'alcanolamine a partir d'acide carboxylique d'herbicides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1293974C true CA1293974C (fr) | 1992-01-07 |
Family
ID=4134646
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000526348A Expired - Fee Related CA1293974C (fr) | 1986-12-29 | 1986-12-29 | Preparation de sels d'alcanolamine a partir d'acide carboxylique d'herbicides |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA1293974C (fr) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110124506A1 (en) * | 2009-11-23 | 2011-05-26 | Dow Agrosciences Llc | Process for preparing soluble granules of salts of pyridine containing carboxylic acids |
| US9743662B2 (en) | 2012-11-05 | 2017-08-29 | Monsanto Technology Llc | Auxin herbicidal mixtures |
| US10285404B2 (en) | 2013-02-27 | 2019-05-14 | Monsanto Technology Llc | Glyphosate composition for dicamba tank mixtures with improved volatility |
| US10334849B2 (en) | 2011-10-26 | 2019-07-02 | Monsanto Technology Llc | Salts of carboxylic acid herbicides |
| US10499646B2 (en) | 2004-03-10 | 2019-12-10 | Monsanto Technology Llc | Herbicidal compositions containing N-phosphonomethyl glycine and an auxin herbicide |
| CN110839632A (zh) * | 2018-08-20 | 2020-02-28 | 四川利尔作物科学有限公司 | 一种除草组合物 |
| US10736322B2 (en) | 2012-06-04 | 2020-08-11 | Monsanto Technology Llc | Aqueous concentrated herbicidal compositions containing glyphosate salts and dicamba salts |
| WO2021028375A1 (fr) * | 2019-08-13 | 2021-02-18 | Bayer Aktiengesellschaft | Bénazoline-choline et son utilisation dans le domaine agrochimique |
-
1986
- 1986-12-29 CA CA000526348A patent/CA1293974C/fr not_active Expired - Fee Related
Cited By (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10499646B2 (en) | 2004-03-10 | 2019-12-10 | Monsanto Technology Llc | Herbicidal compositions containing N-phosphonomethyl glycine and an auxin herbicide |
| US11864558B2 (en) | 2004-03-10 | 2024-01-09 | Monsanto Technology Llc | Herbicidal compositions containing N-phosphonomethyl glycine and an auxin herbicide |
| WO2011063312A3 (fr) * | 2009-11-23 | 2012-01-19 | Dow Agrosciences Llc | Procédé amélioré de préparation de granulés solubles de sels d'acides carboxyliques contenant de la pyridine |
| CN102612319A (zh) * | 2009-11-23 | 2012-07-25 | 陶氏益农公司 | 用于制备吡啶-羧酸的盐的可溶颗粒的改进方法 |
| US8669209B2 (en) | 2009-11-23 | 2014-03-11 | Dow Agrosciences, Llc. | Process for preparing soluble granules of salts of pyridine containing carboxylic acids |
| AU2010321776B2 (en) * | 2009-11-23 | 2014-04-03 | Corteva Agriscience Llc | Improved process for preparing soluble granules of salts of pyridine - carboxylic acids |
| CN105409937A (zh) * | 2009-11-23 | 2016-03-23 | 陶氏益农公司 | 用于制备吡啶-羧酸的盐的可溶颗粒的改进方法 |
| CN105409937B (zh) * | 2009-11-23 | 2018-06-01 | 陶氏益农公司 | 用于制备吡啶-羧酸的盐的可溶颗粒的改进方法 |
| US20110124506A1 (en) * | 2009-11-23 | 2011-05-26 | Dow Agrosciences Llc | Process for preparing soluble granules of salts of pyridine containing carboxylic acids |
| US10334849B2 (en) | 2011-10-26 | 2019-07-02 | Monsanto Technology Llc | Salts of carboxylic acid herbicides |
| US10736322B2 (en) | 2012-06-04 | 2020-08-11 | Monsanto Technology Llc | Aqueous concentrated herbicidal compositions containing glyphosate salts and dicamba salts |
| US10485232B2 (en) | 2012-11-05 | 2019-11-26 | Monsanto Technology Llc | Auxin herbicidal mixtures |
| US11452290B2 (en) | 2012-11-05 | 2022-09-27 | Monsanto Technology Llc | Auxin herbicidal mixtures |
| US9743662B2 (en) | 2012-11-05 | 2017-08-29 | Monsanto Technology Llc | Auxin herbicidal mixtures |
| US10285404B2 (en) | 2013-02-27 | 2019-05-14 | Monsanto Technology Llc | Glyphosate composition for dicamba tank mixtures with improved volatility |
| US11399544B2 (en) | 2013-02-27 | 2022-08-02 | Monsanto Technology Llc | Glyphosate composition for dicamba tank mixtures with improved volatility |
| US12458027B2 (en) | 2013-02-27 | 2025-11-04 | Monsanto Technology Llc | Glyphosate composition for dicamba tank mixtures with improved volatility |
| CN110839632A (zh) * | 2018-08-20 | 2020-02-28 | 四川利尔作物科学有限公司 | 一种除草组合物 |
| WO2021028375A1 (fr) * | 2019-08-13 | 2021-02-18 | Bayer Aktiengesellschaft | Bénazoline-choline et son utilisation dans le domaine agrochimique |
| US20220324822A1 (en) * | 2019-08-13 | 2022-10-13 | Bayer Aktiengesellschaft | Benazolin-choline and its use in the agrochemical field |
| US12435050B2 (en) * | 2019-08-13 | 2025-10-07 | Bayer Aktiengesellschaft | Benazolin-choline and its use in the agrochemical field |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |