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 
• 118-48-9 isatoic anhydride 
• 642474-94-0 N-(2-carbamoylphenyl)-3,4-dichloro-1,2-thiazole-5-carboxamide 

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 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.

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

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.