CN114702422A - Preparation method of diafenthiuron technical - Google Patents
Preparation method of diafenthiuron technical Download PDFInfo
- Publication number
- CN114702422A CN114702422A CN202111606745.9A CN202111606745A CN114702422A CN 114702422 A CN114702422 A CN 114702422A CN 202111606745 A CN202111606745 A CN 202111606745A CN 114702422 A CN114702422 A CN 114702422A
- Authority
- CN
- China
- Prior art keywords
- technical
- diafenthiuron
- preparation
- etherification
- bromination
- 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
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 abstract description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract description 6
- 230000031709 bromination Effects 0.000 abstract description 4
- 238000005893 bromination reaction Methods 0.000 abstract description 4
- 238000006266 etherification reaction Methods 0.000 abstract description 4
- KDGQGEKLPWYCGO-UHFFFAOYSA-N 1-butoxybutane;urea Chemical compound NC(N)=O.CCCCOCCCC KDGQGEKLPWYCGO-UHFFFAOYSA-N 0.000 abstract description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract description 3
- RBDFBEPKVUICAS-UHFFFAOYSA-N [4-phenoxy-2,6-di(propan-2-yl)phenyl]thiourea Chemical compound CC(C)C1=C(NC(N)=S)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 RBDFBEPKVUICAS-UHFFFAOYSA-N 0.000 abstract description 3
- 150000001412 amines Chemical class 0.000 abstract description 3
- 238000000197 pyrolysis Methods 0.000 abstract description 3
- 239000000575 pesticide Substances 0.000 abstract description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 241000238876 Acari Species 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 241001414720 Cicadellidae Species 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- 241000256259 Noctuidae Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000003958 fumigation Methods 0.000 description 1
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000003151 ovacidal effect Effects 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 238000005732 thioetherification reaction Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/74—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by halogenation, hydrohalogenation, dehalogenation, or dehydrohalogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
- C07C331/16—Isothiocyanates
- C07C331/28—Isothiocyanates having isothiocyanate groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C335/18—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a preparation method of a diafenthiuron technical. The invention combines three steps of bromination, etherification and thiourea into a synthetic intermediate 2, 6-diisopropyl-4-phenoxyphenylthiourea by using a continuous reaction, and then the raw pesticide butyl ether urea is synthesized by pyrolysis and amine. The content of the diafenthiuron technical reaches more than 95 percent, and the yield is effectively improved compared with the prior art.
Description
Technical Field
The invention relates to a preparation method of a diafenthiuron technical, belonging to the technical field of pesticide preparation.
Background
Diafenthiuron is a new type thiourea as high-efficiency insecticide and acaricide, has the functions of contact poisoning, stomach toxicity, systemic absorption and fumigation, has a certain ovicidal effect, is low in toxicity, is converted into a substance with insecticidal activity under ultraviolet light, and has stronger activity on pests with serious drug resistance on vegetables. Can be used for preventing and treating aphid, whitefly, leafhopper, noctuidae pests and mites on various crops and ornamental plants.
In the existing preparation process of diafenthiuron, a multi-step method is adopted for preparation, the preparation process flow is complex, the control factors are more, the yield cannot be effectively controlled, and further improvement is needed.
Disclosure of Invention
The invention aims to overcome the defects and provides a preparation method of diafenthiuron technical with simple process and high yield.
The technical scheme adopted by the invention is as follows:
the invention has the advantages that: according to the invention, three steps of bromination, etherification and thiosemicarbazide are combined into a synthetic intermediate 2, 6-diisopropyl-4-phenoxyphenylthiourea by using a continuous reaction, and then the raw material of the butylether urea is synthesized by pyrolysis and amine; the content of the diafenthiuron technical reaches more than 95 percent, and the yield is effectively improved compared with the prior art.
Detailed Description
The technical scheme adopted by the invention is as follows:
the invention combines three steps of bromination, etherification and thiourea into a synthetic intermediate by utilizing a continuous reaction
2, 6-diisopropyl-4-phenoxyphenylthiourea, and then synthesizing the raw material butyl ether urea through pyrolysis and amine; the innovation point of the invention is that the continuous reaction, namely combining three steps of bromination, etherification and thioetherification into one step, and the reaction conditions, such as reaction temperature, molar ratio of each material and the like, can be obtained by those skilled in the art according to the prior art, so that no further description is made herein, and therefore the above description does not affect the clear and complete technical scheme of the application.
Claims (1)
1. The preparation method of the diafenthiuron technical is characterized by comprising the following steps:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111606745.9A CN114702422A (en) | 2021-12-26 | 2021-12-26 | Preparation method of diafenthiuron technical |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111606745.9A CN114702422A (en) | 2021-12-26 | 2021-12-26 | Preparation method of diafenthiuron technical |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN114702422A true CN114702422A (en) | 2022-07-05 |
Family
ID=82166028
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111606745.9A Pending CN114702422A (en) | 2021-12-26 | 2021-12-26 | Preparation method of diafenthiuron technical |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114702422A (en) |
-
2021
- 2021-12-26 CN CN202111606745.9A patent/CN114702422A/en active Pending
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| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |