500008-45-7

Basic information

• Product Name: CHLOANTRANILIPROLE
• Synonyms: CHLOANTRANILIPROLE;CHLORANTRANILIPROLE;3-Bromo-N-[4-chloro-2-methyl-6-[(methylamino)carbonyl]phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide;3-Bromo-4-chloro-1-(3-chloro-2-pyridyl)-2-methyl-6-(methylcarbamoyl)pyrazole-5-carboxanilide;Chlorantraniliprole [iso];Rynaxpyr;Chlorantranilipol;DPX E2Y45
• CAS NO: 500008-45-7
• Molecular Formula: C₁₈H₁₄BrCl₂N₅O₂
• Molecular Weight: 483.152
• Product Categories: Agro-Products;pesticide
• Mol File: 500008-45-7.mol
• Article Data: 24

Chemical Properties

• Melting Point: approximate 225℃ (dec.)
• Boiling Point: 526.6 ºC at 760 mmHg
• Flash Point: 272.3 ºC
• Appearance: /
• Density: 1.66 g/cm³
• Vapor Pressure: 3.51E-11mmHg at 25°C
• Refractive Index: 1.699
• Storage Temp.: 2-8°C
• PKA: 10.19±0.70(Predicted)
• CAS DataBase Reference: CHLOANTRANILIPROLE(CAS DataBase Reference)
• NIST Chemistry Reference: CHLOANTRANILIPROLE(500008-45-7)
• EPA Substance Registry System: CHLOANTRANILIPROLE(500008-45-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37
• Safety Statements: 26
• Hazardous Substances Data: 500008-45-7(Hazardous Substances Data)

Usage

Description

Chlorantraniliprole, also known as Rynaxpyr, is an anthranilic diamide insecticide belonging to the ryanoid class. It is a selective insecticide with a novel mode of action (group 28 in the IRAC classification) and is the first anthranilic diamide registered for use on turfgrass and landscape ornamentals. Developed by DuPont, it is characterized by its high efficiency and broad-spectrum control over various pests. Chlorantraniliprole is a white crystalline compound with specific properties such as a melting point of 208-210℃ and a decomposition temperature of 330℃.

Uses

1. Used in Pesticide detection (Solution)
Chlorantraniliprole is used as an activator of insect ryanodine receptors for pesticide detection purposes.
2. Used in Agriculture
Chlorantraniliprole is used as an insecticide for controlling a broad spectrum of pests, including cabbage loopers, corn borers, Colorado potato beetle, European grapevine moth, armyworms, and cutworms on a range of crops such as potatoes and cotton.
3. Used in Insect Control on Turfgrass and Landscape Ornamentals
Chlorantraniliprole is used as an insecticide for controlling pests on turfgrass and landscape ornamentals, providing effective and selective control.
4. Used in Control of Insects of the Order Lepidoptera
Chlorantraniliprole is used as an insecticide for controlling insects of the order Lepidoptera, such as the fall armyworm, diamondback moth, and tobacco budworm, as well as other insects from the orders Coleoptera, Diptera, and Isoptera.
5. Used in Ryanodine Receptor Activation
Chlorantraniliprole is used as a ryanodine receptor activator, which plays a role in its insecticidal action by stimulating the release of calcium from intracellular stores, leading to impaired muscle regulation, paralysis, and death of sensitive species.
6. Used in Protection of Various Crops
Chlorantraniliprole is used to protect a wide variety of crops, including corn, cotton, grapes, rice, and potatoes, by acting as a ryanodine receptor agonist and providing effective control against targeted pests.

Preparation

Chlorantraniliprole was synthesized by reaction of 3-bromo-1-(3-chloropyridin-2-pyridinyl)-1H-pyrazole-5carboxylic acid with 2-amino-5-chloro-3-methylbenzoic acid.3-bromo-1-(3-chloropyridin-2-pyridinyl)-1H-pyrazole5-carboxylic acid was prepared by reaction of maleic anhydride with 2,3-dichloropyridine as starting materials in eight steps.2-Amino-5-chloro-3-methylbenzoic acid was prepared by reaction of 2-amino-3-methylbenzoic acid in one step.The structure of target compound was conf irmed by 1H NMR.Total yield was 36.3%(calculated with 2,3-dichloropyridine),and purity determined by HPLC was over 95%.

InChI:InChI=1/C18H14BrCl2N5O2/c1-9-6-10(20)7-11(17(27)22-2)15(9)24-18(28)13-8-14(19)25-26(13)16-12(21)4-3-5-23-16/h3-8H,1-2H3,(H,22,27)(H,24,28)

Upstream product

• 500011-87-0 6-chloro-2-(3-bromo-1-(3-chloropyridin-2-yl)-1Hpyrazol-5-yl)-8-methyl-4H-benzo[d][1,3]oxazin-4-one 
• 74-89-5 methylamine 
• 500011-86-9 3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxylic acid 
• 890707-28-5 2-amino-3-methyl-5-chlorobenzoyl-N-methylamine 
• 120374-68-7 6-chloro-8-methyl-1H-benzo[d][1,3]oxazine-2,4-dione 
• 943982-60-3 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbonyl chloride 
• 146948-68-7 2-bromo-4-chloro-6-methylphenylamine 
• 4389-45-1 3-methylantranilic acid 
• 20776-67-4 2-amino-5-chloro-3-methylbenzoic acid 
• 2402-77-9 2,3-dichloro-pyridine 
• 22841-92-5 (3-chloro-2-pyridyl)hydrazine 
• 95-53-4 o-toluidine 
• 500011-88-1 2-(3-chloro-pyridin-2-yl)-5-oxo-pyrazolidine-3-carboxylic acid ethyl ester 
• 500011-91-6 5-bromo-2-(3-chloro-pyridin-2-yl)-3,4-dihydro-2H-pyrazole-3-carboxylic acid ethyl ester 

Relevant articles and documents

PROCESS FOR THE PREPARATION OF CHLORANTRANILIPROLE

The present disclosure relates to a process for the preparation of Chlorantraniliprole. The process of the present disclosure is carried out at an ambient temperature by using an inorganic base which can be readily separated from Chlorantraniliprole. The process is simple, efficient, environment friendly, and provides Chlorantraniliprole with high purity and high yield.

PROCESS FOR PREPARATION OF ARTHROPODICIDAL ANTHRANILAMIDE COMPOUNDS

The present invention provides a process for preparation of arthropodicidal anthranilamide compounds. The present invention further relates to one pot process for preparation of anthranilamide compounds.

PROCESS FOR THE PREPARATION OF CHLORANTRANILIPROLE

The present invention relates to two novel, efficient and one-pot methods for synthesizing chlorantraniliprole. In the first scheme, Chlorantraniliprole is prepared by a novel telescopic process starting from 3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid a key raw material-A (Key RM-A). In the second scheme, starting from Key RM-A, the process steps use of a novel variant of anthranilic acid (Methyl 2-amino-5-chloro-3-methylbenzoate), to get Chlorantraniliprole. Furthermore, the present invention also relates to the synthesis of key starting material for the synthesizing chlorantraniliprole in-situ. All the in-situ steps of the disclosed synthesis methods obtain good yield, without using any expensive reagent or base or harsh reaction conditions, which makes the process simple, environment friendly and more cost effective. With this process the production cost of chlorantraniliprole and its intermediates is substantially reduced; fewer by-products are formed during its synthesis and since it's a one-pot reaction, isolation and purification are easy to achieve.