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

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

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

• 500011-86-9 3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxylic acid 
• 120374-68-7 6-chloro-8-methyl-1H-benzo[d][1,3]oxazine-2,4-dione 
• 74-89-5 methylamine 
• 943982-60-3 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbonyl chloride 
• 79101-83-0 2-amino-3-methyl-5-chlorobenzoic acid methyl ester 
• 870997-57-2 N-methyl-3-methyl-2-aminobenzamide 
• 600126-70-3 N-3-dimethyl-2-nitrobenzamide 
• 5437-38-7 3-methyl-2-nitrobenzoic acid 
• 99-04-7 m-Toluic acid 
• 20776-67-4 2-amino-5-chloro-3-methylbenzoic acid 
• 1045077-26-6 3-bromo-1-(3-chloropyridine-2-yl)-1H-pyrazole-5-carboxylic acid methyl ester 
• 890707-28-5 2-amino-3-methyl-5-chlorobenzoyl-N-methylamine 
• 500011-89-2 ethyl 5-chloro-2-(3-chloropyridin-2-yl)-3,4-dihydro-2H-pyrazole-3-carboxylate 
• 22841-92-5 3-chloro-2(1H)-pyridinone hydrazone 

Relevant articles and documents

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.

Preparation method of chlorantraniliprole

The invention relates to the field of insecticide synthesis, and discloses a preparation method of chlorantraniliprole. The preparation method comprises the following steps: synthesis of an intermediate I, synthesis of an intermediate II and synthesis of chlorantraniliprole. The method comprises the following steps: reacting 2, 3, 6-trichloropyridine serving as a raw material with hydrazine hydrate under the action of a catalyst A to obtain 3, 6-dichloro-2-hydrazinopyridine, carrying out hydrogenation reduction reaction under the action of a catalyst B to obtain an intermediate I, reacting theintermediate I with diethyl maleate, and preparing the 2-(3-chloropyridine-2-yl)-5-hydroxypyrazole-3-ethyl formate under the action of a catalyst C, and hydrolyzing after bromination to obtain an intermediate II, and preparing chlorantraniliprole from the intermediate II. According to the invention, 2, 3, 6-trichloropyridine is adopted to replace 2, 3-dichloropyridine as a raw material to preparethe intermediate I, so that the defects of difficulty in obtaining the 2, 3-dichloropyridine raw material, harsh synthesis conditions, low yield and the like are avoided, the total reaction yield ofthe intermediate I is improved, the intermediate II is prepared by a one-pot method, the post-treatment operation is reduced, and the synthesis cost of chlorantraniliprole is reduced.

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.

Method for synthesizing chlorantraniliprole

A solvent containing 2 - amino -3 - methylbenzoic acid is stirred, N - methyl -3 - methyl -2 - amino - benzamide is dissolved in alkali liquor in a stirring reaction process, and reacted with NCS to obtain N - methyl -3 - methyl -2 - amino -5 - chloro - benzamide. The reaction of the bromination reaction, the oxidation reaction and the condensation reaction is carried out by cooperation of a catalyst so as to obtain chlorantraniliprole. By optimizing the preparation steps of chlorantraniliprole, the whole process is relatively simple in process steps, the post-treatment is simple, intermediate products can be obtained directly after the single step is finished, high environmental control requirements are not needed in the whole synthesis step, and industrialization can be conveniently realized.

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.

Method for synthesizing chlorantraniliprole

The invention discloses a synthesis method of chlorantraniliprole, which comprises the following steps: dissolving phosgene in a solvent to form a material A, mixing 3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxylic acid and 2-amino-5-chloro-3-methylbenzoic acid as raw materials in the presence of alkali and the solvent, and adding the material A to carry out a reaction to obtain 2-(3-Bromo-1-(3-chloro-2-pyridyl)-1H-5-pyrazolyl)-6-chloro-8-methyl-4H-benzo[d][1,3]oxazine-4-one (oxazinone, for short), and directly reacting the oxazinone with monomethylamine without purification to synthesize the chlorantraniliprole. The synthesis method has the advantages of cheap raw materials, high reaction activity, simple post-treatment process and no residue; the reaction synthesis conditions aremild, less three wastes are generated, special equipment is not needed, and industrial production is easy to realize.

PROCESS FOR PREPARATION OF ANTHRANILAMIDES

The present invention provides a process for preparation and purification of anthranilamides.

METHOD FOR PREPARING N-PHENYLPYRAZOLE-1-CARBOXAMIDES

A method is disclosed for preparing compounds of Formula 1 by combining compounds of Formulae 2 and 3 and a sulfonyl chloride in a continuous process.

Preparation method of chlorantraniliprole

The invention relates to the technical field of synthesis processes of insecticides, and discloses a preparation method of chlorantraniliprole, which comprises the following steps: 1) adding 4-8 partsof maleic anhydride and 4-8 parts of methanol into a single-necked bottle, stirring the mixture, heating to 50 DEG C, and carrying out heat preservation reaction for 0.5-1.5 hours to obtain monomethyl maleate; and 2) cooling 80-120 parts of a hydrogen bromide-glacial acetic acid solution to 0 DEG C, then dropwise adding 3-5 parts of the monomethyl maleate, after addition is completed, carrying out heat preservation and stirring for 3-7 min, so that a large amount of a yellow viscous substance appears, and the monomethyl 3-bromomaleate can be prepared. The invention discloses a preparation method of chlorantraniliprole. The maleic anhydride, 2,3-dichloropyridine and 2-amino-3-methylbenzoic acid are adopted as starting materials to synthesize the target compound chlorantraniliprole througha convergent reaction. The structure is determined through HNMR, the route is mild in reaction condition, easy and convenient to operate and separate, raw materials are easy to obtain, special equipment is not needed, industrial production is easy to achieve, the action mechanism is novel and unique, and wide application and development prospects are achieved.

Method for preparing benzamide compound by using pressure reducing method

The invention relates to a method for preparing a benzamide compound represented by a general formula (I), wherein the reaction formula is defined in the specification, and each group in the formula is defined in the specification. According to the method, 3-bromo-1-(substituted pyridyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acid (IV) is used as a raw material, and is simultaneously subjected to acyl chlorination and oxidation under a pressure reducing condition to prepare acyl chloride represented by a general formula (III), and the benzamide compound represented by the general formula (I) isprepared from the acyl chloride (III) and substituted aniline (II) in the absence of an acid-binding agent in a high yield manner.