CN105061306A - Boscalid preparation method - Google Patents
Boscalid preparation method Download PDFInfo
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- CN105061306A CN105061306A CN201510476648.0A CN201510476648A CN105061306A CN 105061306 A CN105061306 A CN 105061306A CN 201510476648 A CN201510476648 A CN 201510476648A CN 105061306 A CN105061306 A CN 105061306A
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- preparation
- boscalid
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- boscalid amine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
Abstract
The invention discloses a boscalid preparation method, which relates to the technical field of chemistry. The preparation method comprises the steps of pretreatment, MS-Pd catalysis, hydrogen reduction and hierarchical processing. By taking o-chloronitrobenzene and chlorophenylboronic acid as raw materials, boscalid can be prepared under existence of a catalyst MS-Pd, anhydrous potassium carbonate and a DMF solution. The method for synthesizing boscalid by employing the catalyst MS-Pd, anhydrous potassium carbonate and the DMF solution. The method has the advantages of simple process, mild reaction condition and low production cost, and has good industrial application prospect.
Description
Technical field
The present invention relates to chemical technology field, be specifically related to the preparation method of boscalid amine class.
Background technology
Boscalid amine (boscalid) is the Novel tobacco acid amide fungicides developed by BASF Aktiengesellschaft.Molecular formula: C18H12C12N20, molecular weight: 343.21.The chloro-N ' of chemical name: 2--(4 '-chlordiphenyl-2-base) niacinamide (IUPAC).
Boscalid amine belongs to succsinic acid ubiquinone reductase inhibitor in mitochondrial respiratory chain, has very strong rejection ability to the sprouting of spore, and with other sterilant without cross resistance.Liquid is permeated by blade face through plant absorption, is then transferred in plant, can suppress mitochondrial succinate acid esters dehydrogenase activity, thus hinders tricarboxylic acid cycle, and make amino acid, sugar lacks, energy reduces, the division of interference cell and growth and have fungicidal activity.This medicament disinfecting spectrum is comparatively wide, can be used for various crop and prevent and treat the multiple fungal diseases such as gray mold, and also effective to the resistance bacterium of other medicaments.Be mainly used in preventing and treating Powdery Mildew, gray mold, various canker, brown heart and root rot etc.Because it is to crop safety, ecological effect is better, is the Novel tobacco acid amide fungicides of significant.At present, abroad the research of boscalid amine is enlivened, domestic few to its research report.
Summary of the invention
Problem to be solved by this invention is to provide a kind of preparation method of boscalid amine class.
To achieve these goals, the technical scheme that the present invention takes is: a kind of preparation method of boscalid amine class, comprises the steps:
(1) pre-treatment: join in the DMF solution solvent of Anhydrous potassium carbonate and TBAB to chlorophenylboronic acid raw material by 45%-55% o-chloronitrobenzene and 55%-45%, stirs 10-30min, makes abundant dissolving;
(2) MS-Pd catalysis: catalyzer MS-Pd is added to step (1) afterwards in solution, be heated to 115-120 DEG C, insulation 10-30min, makes abundant reaction;
(3) hydrogen reduction: by step (2) afterwards solution be down to room temperature, slowly add distilled water, recycling hydrogen catalysis reduction, make abundant reaction;
(4) layered shaping: utilize 2-chloronicotinoyl chloride to carry out condensation, layering, precipitation to step (3) solution, boscalid amine class.
Preferably, described step (1) raw material comprises following component (massfraction): adjacent chlorine nitro 45%, benzene chlorophenylboronic acid 55%.
Preferably, o-chloronitrobenzene and be 25 DEG C to the temperature of the abundant dissolving of chlorophenylboronic acid in described step (1) raw material.
Beneficial effect of the present invention: by o-chloronitrobenzene and chlorophenylboronic acid raw material are joined in the DMF solution solvent of Anhydrous potassium carbonate and TBAB, after dissolving, add catalyzer MS-Pd, be warmed up to 120 DEG C of reactions, after monitoring has been reacted, add water under being down to room temperature, the reduction of recycling hydrogen catalysis, after monitoring has been reacted, the condensation of recycling 2-chloronicotinoyl chloride, layering, precipitation, obtained boscalid amine class.The present invention has the advantages such as technique is simple, reaction conditions is gentle, reaction yield is high, production cost is low, has good prospects for commercial application.
Embodiment
The technique means realized for making the present invention, creation characteristic, reaching object and effect is easy to understand, below in conjunction with embodiment, setting forth the present invention further.
Chemical equation of the present invention:
embodiment 1:
(1) pre-treatment: 45% o-chloronitrobenzene and 55% pair of chlorophenylboronic acid raw material are joined in the DMF solution solvent of Anhydrous potassium carbonate and TBAB, stir 10min, make abundant dissolving, control temperature is 25 DEG C;
(2) MS-Pd catalysis: catalyzer MS-Pd is added to step (1) afterwards in solution, be heated to 120 DEG C, insulation 10min, makes abundant reaction;
(3) hydrogen reduction: by step (2) afterwards solution be down to room temperature, slowly add distilled water, recycling hydrogen catalysis reduction, make abundant reaction;
(4) layered shaping: utilize 2-chloronicotinoyl chloride to carry out condensation, layering, precipitation to step (3) solution, boscalid amine.
embodiment 2:
(1) pre-treatment: 55% o-chloronitrobenzene and 45% pair of chlorophenylboronic acid raw material are joined in the DMF solution solvent of Anhydrous potassium carbonate and TBAB, stir 15min, make abundant dissolving, control temperature is 25 DEG C;
(2) MS-Pd catalysis: catalyzer MS-Pd is added to step (1) afterwards in solution, be heated to 115-120 DEG C, insulation 30min, makes abundant reaction;
(3) hydrogen reduction: by step (2) afterwards solution be down to room temperature, slowly add distilled water, recycling hydrogen catalysis reduction, make abundant reaction;
(4) layered shaping: utilize 2-chloronicotinoyl chloride to carry out condensation, layering, precipitation to step (3) solution, boscalid amine.
Based on above-mentioned, in the present invention, by o-chloronitrobenzene and chlorophenylboronic acid raw material are joined in the DMF solution solvent of Anhydrous potassium carbonate and TBAB, after dissolving, add catalyzer MS-Pd, be warmed up to 120 DEG C of reactions, after monitoring has been reacted, add water under being down to room temperature, the reduction of recycling hydrogen catalysis, after monitoring has been reacted, the condensation of recycling 2-chloronicotinoyl chloride, layering, precipitation, obtained boscalid amine.The present invention has the advantages such as technique is simple, reaction conditions is gentle, reaction yield is high, production cost is low, has good prospects for commercial application.
Obvious specific implementation of the present invention is not subject to the restrictions described above; as long as have employed the improvement of the various unsubstantialities that method of the present invention is conceived and technical scheme is carried out; or design of the present invention and technical scheme directly applied to other occasion, all within protection scope of the present invention without to improve.
Claims (3)
1. a preparation method for boscalid amine class, is characterized in that: comprise the steps:
Pre-treatment: join in the DMF solution solvent of Anhydrous potassium carbonate and TBAB to chlorophenylboronic acid raw material by 45%-55% o-chloronitrobenzene and 55%-45%, stirs 10-30min, makes abundant dissolving;
MS-Pd catalysis: catalyzer MS-Pd is added to step (1) afterwards in solution, be heated to 115-120 DEG C, insulation 10-30min, makes abundant reaction;
Hydrogen reduction: by step (2) afterwards solution be down to room temperature, slowly add distilled water, recycling hydrogen catalysis reduction, make abundant reaction;
Layered shaping: utilize 2-chloronicotinoyl chloride to carry out condensation, layering, precipitation to step (3) solution, boscalid amine.
2. the preparation method of boscalid amine class according to claim 1, is characterized in that, described step (1) raw material comprises following component (massfraction): adjacent chlorine nitro 45%, benzene chlorophenylboronic acid 55%.
3. the preparation method of boscalid amine class according to claim 1, is characterized in that, in described step (1) raw material, o-chloronitrobenzene and the temperature to the abundant dissolving of chlorophenylboronic acid are 25 DEG C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510476648.0A CN105061306A (en) | 2015-08-07 | 2015-08-07 | Boscalid preparation method |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510476648.0A CN105061306A (en) | 2015-08-07 | 2015-08-07 | Boscalid preparation method |
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| CN105061306A true CN105061306A (en) | 2015-11-18 |
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| CN201510476648.0A Pending CN105061306A (en) | 2015-08-07 | 2015-08-07 | Boscalid preparation method |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5330995A (en) * | 1991-11-22 | 1994-07-19 | Basf Aktiengesellschaft | Anilide derivatives and their use for combating botrytis |
| CN104478797A (en) * | 2014-12-09 | 2015-04-01 | 苏州至善化学有限公司 | Preparation method of nicotinamide fungicide namely boscalid |
| CN104725303A (en) * | 2015-02-02 | 2015-06-24 | 西安近代化学研究所 | Synthetic method of 2-chloro-N-(4'-chlorodiphenyl-2-yl) nicotinamide |
-
2015
- 2015-08-07 CN CN201510476648.0A patent/CN105061306A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5330995A (en) * | 1991-11-22 | 1994-07-19 | Basf Aktiengesellschaft | Anilide derivatives and their use for combating botrytis |
| CN104478797A (en) * | 2014-12-09 | 2015-04-01 | 苏州至善化学有限公司 | Preparation method of nicotinamide fungicide namely boscalid |
| CN104725303A (en) * | 2015-02-02 | 2015-06-24 | 西安近代化学研究所 | Synthetic method of 2-chloro-N-(4'-chlorodiphenyl-2-yl) nicotinamide |
Non-Patent Citations (10)
| Title |
|---|
| RAJU DEY,等: "Molecular sieves-supported palladium(II) catalyst: Suzuki coupling of chloroarenes and an easy access to useful intermediates for the synthesis of irbesartan,losartan and boscalid", 《TETRAHEDRON》 * |
| TOMA N. GLASNOV,等: "Toward a Continuous-Flow Synthesis of Boscalid", 《ADVANCED SYNTHESIS&CATALYSIS》 * |
| 于康平: "啶酰菌胺及其同系物的合成及杀菌活性研究", 《现代农药》 * |
| 吴鸿飞,等: "啶酰菌胺合成方法述评", 《农药》 * |
| 孙斌,等: "啶酰菌胺的合成研究", 《化学研究与应用》 * |
| 张晓光,等: "啶酰菌胺的合成研究进展", 《精细化工中间体》 * |
| 成红丽,等: "啶酰菌胺的合成工艺改进研究", 《武汉生物工程学院学报》 * |
| 王凤卓: "啶酰菌胺的合成工艺改进研究", 《江西化工》 * |
| 迟会伟,等: "啶酰菌胺的合成与生物活性研究", 《精细化工中间体》 * |
| 黄晓瑛,等: "杀菌剂啶酰菌胺合成方法", 《农药科学与管理》 * |
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