224049-04-1

Basic information

• Product Name: Isotianil
• Synonyms: 3,4-Dichloro-N-(2-cyanophenyl)-5-isothiazolecarboxamide
• CAS NO: 224049-04-1
• Molecular Formula: C₁₁H₅Cl₂N₃OS
• Molecular Weight: 298.1479
• Mol File: 224049-04-1.mol

Chemical Properties

• Boiling Point: 322.771°C at 760 mmHg
• Flash Point: 149.007°C
• Appearance: /
• Density: 1.6g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.675
• PKA: 9.15±0.70(Predicted)
• CAS DataBase Reference: Isotianil(CAS DataBase Reference)
• NIST Chemistry Reference: Isotianil(224049-04-1)
• EPA Substance Registry System: Isotianil(224049-04-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36-43
• Safety Statements: 26-36/37
• WGK Germany: 3
• Hazardous Substances Data: 224049-04-1(Hazardous Substances Data)

Usage

Uses

Used in Agriculture:
Isotianil is used as a fungicide for the control of rice blast, a fungal disease that significantly affects rice crops. Its application helps in protecting the crops from the damaging effects of the disease, ensuring a healthy and productive yield.
Used in Crop Protection Industry:
In the crop protection industry, Isotianil is utilized as a key component in the development of fungicides and other protective agents. Its role in controlling rice blast makes it a valuable asset in the fight against crop diseases, contributing to the overall food security and agricultural sustainability.

InChI:InChI=1/C11H5Cl2N3OS/c12-8-9(18-16-10(8)13)11(17)15-7-4-2-1-3-6(7)5-14/h1-4H,(H,15,17)

Upstream product

• 56914-82-0 3,4-dichloro-isothiazole-5-carbonyl chloride 
• 1885-29-6 anthranilic acid nitrile 
• 28144-70-9 anthranilic acid amide 
• 642474-94-0 N-(2-carbamoylphenyl)-3,4-dichloro-1,2-thiazole-5-carboxamide 
• 118-48-9 isatoic anhydride 

Relevant articles and documents

METHOD FOR PRODUCING 3,4-DICHLORO-N-(2-CYANOPHENYL)-5-ISOTHIAZOLECARBOXAMIDE

The present invention relates to a novel, one-stage method for preparing and isolating 3,4-dichloro-N-(2-cyanophenyl)-5-isothiazolecarboxamide (isotianil), which has microbicidal and plant-fortifying (host defence inducer) properties. In the method accord

Synthesis, Structure, and Spectroscopic Properties of Isotianil as a Bactericide

Abstract: Isotianil [N-(2-cyanophenyl)-3,4-dichloro-1,2-thiazole-5-carboxamide] has beensynthesized in a good yield with high purity by reaction of the key intermediateproduct, N-(2-carbamoylphenyl)-3,4-dichloro-1,2-thiazole-5-carboxamide, withthionyl chloride in N,N-dimethylformamide at 60°C. The structure of isotianil wasstudied by X-ray analysis. It crystallized in triclinic space group P1 with a =11.459(3), b = 12.632(3), c = 22.528(5) ?, α = 78.897(3), β = 81.730(3), γ =71.493(3)°, Z = 10.

PROCESS FOR PREPARING 3,4-DICHLORO-N-(2-CYANOPHENYL)-5-ISOTHIAZOLECARBOXAMIDE

The present invention relates to a novel process for preparing and isolating 3,4-dichloro-N-(2-cyanophenyl)-5-isothiazolecarboxamide (Isotianil), which can be used as an active compound with microbicidal properties, wherein the amount of waste materials - e.g. solvents and diluents - is significantly reduced and the process meets the requirements of industrial scale production, in particular that it provides the product in high yield, high purity, i.e. minimum amount of by-products and impurities, and can be carried out with tolerable corrosivity in industrial scale metal, in particular stainless steel, vessels or Cr-Ni-Mo alloy pressure filters or centrifuges.

PROCESS FOR PREPARING 3,4-DICHLORO-N-(2-CYANOPHENYL)-5-ISOTHIAZOLECARBOXAMIDE

Described is a process for preparing 3,4-dichloro-N-(2-cyanophenyl)-5-isothiazolecarboxamide, by a) reacting 3,4-dichloroisothiazole-5-carbonyl chloride with anthranilamide in the absence or the presence of an acid acceptor and b) then reacting the resulting N-[2-(aminocarbonyl)phenyl]-3,4-dichloro-5-isothiazolecarboxamide with a mixture of a dialkylformamide and thionyl chloride or phosgene as a dehydrating agent. The reactions can be carried out at least partly in the presence of methyl acetate, ethyl acetate or a mixture of these as a diluent. In the course of working up and of isolation, an alcohol may be present.

METHOD FOR PRODUCING 3,4-DICHLORO-N-(2-CYANO-PHENYL)-5-ISOTHIAZOLE CARBOXAMIDE

The invention relates to a novel one-pot method for producing 3,4-dichloro-N-(2-cyano-phenyl)-5-isothiazole carboxamide. According to said method, a) isatoic acid anhydride is reacted with ammonia gas in the presence of dimethylformamide, b) the anthranil

METHOD FOR PRODUCING 3,4-DICHLORO-N-(2-CYANO-PHENYL)-5-ISOTHIAZOLE CARBOXAMIDE

The invention relates to a novel method for producing 3,4-dichloro-N-(2-cyano-phenyl)-5-isothiazole carboxamide. According to said method, a) 3,4-dichloro-isothiazole-5-carboxylic acid chloride is reacted with anthranilic acid amide in the presence of an acid acceptor and an aprotic diluent, and b) the N-[2-(aminocarbonyl)-phenyl]-3,4-dichloro-5-isothiazole carboxamide obtained is reacted with a dehydration agent optionally in the presence of an additional diluent. The N-[2-(aminocarbonyl)-phenyl]-3,4-dichloro-5-isothiazole carboxamide is novel.

Isothiazole carboxylic acid amides and the application thereof in order to protect plants

Novel isothiazolecarboxamides of the formula in which R is as defined in the description, a plurality of processes for preparing the novel compounds and their use for protecting plants against attack by undesirable microorganisms and animal pests.