173584-44-6

Basic information

• Product Name: INDOXACARB
• Synonyms: INDOXACARB-MP;METHYL 7-CHLORO-2,5-DIHYDRO-2-[N-(METHOXYCARBONYL)-4-(TRIFLUOROMETHOXY)ANILINOCARBONYL]INDENO[1,2-E][1,3,4]OXADIAZINE-4A(3H)CARBOXYLATE;Indeno1,2-e1,3,4oxadiazine-4a(3H)-carboxylic acid, 7-chloro-2,5-dihydro-2-(methoxycarbonyl)4-(trifluoromethoxy)phenylaminocarbonyl-, methyl ester, (4aS)-;indoxacarb (bsi, pa iso, ansi);methyl(S)-7-chloro-2,3,4a,5-tetrahydro-2-[methoxycarbonyl(4-trifluoromethoxyphenyl)carbamoyl]indeno[1,2-e][1,3,4]oxadiazine-4a-carboxylate:indoxacarb;Chebi:38630;Methyl (4as)-7-chloro-2-{(methoxycarbonyl)[4-(trifluoromethoxy)phenyl]carbamoyl}-2,5-dihydroindeno[1,2-E][1,3,4]oxadiazine-4A(3H)-carboxylate
• CAS NO: 173584-44-6
• Molecular Formula: C22H17ClF3N3O7
• Molecular Weight: 527.83
• EINECS: 200-258-5
• Product Categories: Insecticides
• Mol File: 173584-44-6.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 571.4 °C at 760 mmHg
• Flash Point: 299.3 °C
• Appearance: /
• Density: 1.537 g/cm³
• Vapor Pressure: 4.59E-13mmHg at 25°C
• Refractive Index: 1.601
• Storage Temp.: 0-6°C
• PKA: -1.75±0.40(Predicted)
• CAS DataBase Reference: INDOXACARB(CAS DataBase Reference)
• NIST Chemistry Reference: INDOXACARB(173584-44-6)
• EPA Substance Registry System: INDOXACARB(173584-44-6)

Safety Data

• Hazardous Substances Data: 173584-44-6(Hazardous Substances Data)

Usage

General Description

Indoxacarb is a pesticide from the oxadiazine chemical class that is used to control insect pests in agriculture and household settings. It works by disrupting the nervous system of insects, causing paralysis and eventually leading to their death. Indoxacarb is considered to be more selective and less harmful to non-target organisms and the environment compared to other insecticides. It is commonly used to control a wide range of insect pests such as Lepidoptera, Coleoptera, and Hemiptera in crops like cotton, maize, soybeans, and vegetables. Additionally, it is used in household pest control products to manage pests like ants, cockroaches, and termites. Due to its low toxicity to mammals, indoxacarb is often used as a safer alternative for pest control.

InChI:InChI=1/C22H17ClF3N3O7/c1-33-18(30)21-10-12-9-13(23)3-8-16(12)17(21)27-28(11-35-21)19(31)29(20(32)34-2)14-4-6-15(7-5-14)36-22(24,25)26/h3-9H,10-11H2,1-2H3/t21-/m0/s1

Upstream product

• 109-87-5 Dimethoxymethane 
• 173903-15-6 chloroformyl(4-trifluoromethoxyphenyl)carbamic acid methyl ester 
• 173903-23-6 C₁₂H₁₁ClN₂O₃ 
• 79-22-1 methyl chloroformate 
• 461-82-5 4-(trifluoromethoxy)aniline 
• 144171-61-9 methyl 7-chloro-2,3,4a,5-tetrahydro-2-[methoxycarbonyl(4-trifluoromethoxyphenyl)carbamoyl]-indeno[1,2-e][1,3,4]oxadiazine-4a-carboxylate 

Downstream Products

• 144171-61-9 indoxacarb 
• 144171-61-9 (S)-methyl-7-chloro-2,3,4a,5-tetrahydro-2-[methoxycarbonyl(4-trifluoromethoxyphenyl)aminoformyl]indeno[1,2-e][1,3,4]oxadiazine-4a-carboxylate 

Relevant articles and documents

Synthesis process of indoxacarb

The invention discloses a synthesis process of indoxacarb. The method comprises the following steps: reacting m-chlorobenzaldehyde serving as a raw material with malonic acid to remove monomolecular water and carbon dioxide to generate an intermediate SRCA, performing a hydrogenation reduction on the intermediate SRCA in an autoclave in the presence of a catalyst to obtain an intermediate SRCH, and cyclizing the SRCH by using hydrogen fluoride as a dehydrating agent to obtain the final product indoxacarb. The synthesis process is simple and easy to implement, energy is saved, consumption is reduced, the yield is increased, and good economic and environmental benefits are obtained.

A New Method for the Synthesis of Oxadiazine Insecticide Indoxacarb

9-Fluorenylmethoxycarbonyl was a good protecting group in the field of chemical industry. In the present paper, a new approach for the synthesis of oxadiazine insecticides indoxacarb used 9-fluorenylmethoxycarbonyl as protected group, and triphosgene for chloroformylation. A convenient synthesis of 9-fluorenylmethoxycarbonylhydrazine can be achieved by the nucleophilic substitution reaction of 9-fluorenylmethyl chloroformate and hydrazine hydrate. 4a-Methyl-2-(9-fluorenylmethyl)-7-chloro-indeno [1,2e][1,3,4]oxadia zine-2,4a (3H,5H)-dicarboxylate can be produced via ketone -hydrazine crosslink reaction and cyclization. A preparation of carbamic acid-(chlorocarbonyl)-[(4-trifluoromethoxy) phenyl] me ester can be obtained by the chloroformylation of triphosgene. Finally, the deprotection of 9-fluorenylmethoxy carbonyl and condensation with carbamic acid-(chlorocarbonyl)-[(4-trifluoromethoxy) phenyl] me ester can afford indoxacarb in good yield. A new method for the synthesis of oxadiazine insecticides indoxacarb used 9-fluorenylmethoxycarbonyl-protected group to produce 9-?fluorenylmethoxycarb?onylhydrazine, then through the ketone–hydrazine crosslink reaction, cyclization, deprotection, chloroformylation, and condensation in good yield.