6957-92-2

Basic information

• Product Name: [(2,4-dichlorophenyl)methylideneamino]thiourea
• Synonyms: [(2,4-dichlorophenyl)methylideneamino]thiourea
• CAS NO: 6957-92-2
• Molecular Formula: C₈H₇Cl₂N₃S
• Molecular Weight: 248.13
• Mol File: 6957-92-2.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 375.4°C at 760 mmHg
• Flash Point: 180.8°C
• Appearance: /
• Density: 1.49g/cm³
• Vapor Pressure: 7.79E-06mmHg at 25°C
• Refractive Index: 1.659
• CAS DataBase Reference: [(2,4-dichlorophenyl)methylideneamino]thiourea(CAS DataBase Reference)
• NIST Chemistry Reference: [(2,4-dichlorophenyl)methylideneamino]thiourea(6957-92-2)
• EPA Substance Registry System: [(2,4-dichlorophenyl)methylideneamino]thiourea(6957-92-2)

Safety Data

• Hazardous Substances Data: 6957-92-2(Hazardous Substances Data)

Usage

General Description

The chemical [(2,4-dichlorophenyl)methylideneamino]thiourea, also known as dichlorphenamid, is a white crystalline solid used as a fungicide to protect plants from various fungal diseases. It works by inhibiting the development and spread of fungal infections by interfering with the formation of their cell walls. [(2,4-dichlorophenyl)methylideneamino]thiourea is considered relatively low in toxicity to humans and has been approved for use in agriculture by various regulatory authorities. However, it is important to handle and apply dichlorphenamid with caution and in accordance with safety guidelines to minimize potential risks to human health and the environment.

InChI:InChI=1/C8H7Cl2N3S/c9-6-2-1-5(7(10)3-6)4-12-13-8(11)14/h1-4H,(H3,11,13,14)/b12-4+

Upstream product

• 874-42-0 2,4-dichlorobenzaldeyhde 
• 79-19-6 thiosemicarbazide 

Downstream Products

• 106320-49-4 2,4-dichloro-benzaldehyde (4-oxo-5-propyl-thiazolidin-2-ylidene)-hydrazone 
• 100710-15-4 2,4-dichloro-benzaldehyde (5-butyl-4-oxo-thiazolidin-2-ylidene)-hydrazone 
• 134951-56-7 [2-(2,4-Dichloro-phenyl)-4-oxo-thiazolidin-3-yl]-thiourea 
• 128391-18-4 Cu⁽¹⁺⁾*C₈H₆Cl₂N₃S^(1-)={Cu(C₆H₃Cl₂CHNNCSNH₂)} 
• 467246-65-7 C₂₀H₁₃Cl₂N₃S 
• 1248828-24-1 2-[{5-(2,4-dichlorolphenyl)-[1,3,4]-thiadiazol-2-yl}imino]-1,3-thiazolidin-4-one 
• 1233091-88-7 2-chloro-N-[5-(2,4-dichlorophenyl)-[1,3,4]-thiadiazol-2-yl]-acetamide 
• 1431555-44-0 4-[[5-(2,4-dichlorophenyl)-1,3,4-thiadiazol-2-ylimino]-methyl]phenol 
• 134834-90-5 1-[1-Acetyl-3-benzylsulfanyl-5-(2,4-dichloro-phenyl)-1,5-dihydro-[1,2,4]triazol-4-yl]-ethanone 
• 134951-55-6 2-(2,4-Dichloro-phenyl)-3-[4-oxo-thiazolidin-(2E)-ylideneamino]-thiazolidin-4-one 
• 134951-57-8 6-(2,4-Dichloro-phenyl)-1,5-dithia-3a,6a,7-triaza-cyclopenta[a]pentalen-3-one 
• 134951-54-5 2-{[1-(2,4-Dichloro-phenyl)-meth-(E)-ylidene]-hydrazono}-thiazolidin-4-one 
• 134834-82-5 C₁₅H₁₃Cl₂N₃S*ClH 

Relevant articles and documents

Synthesis, in vitro thymidine phosphorylase activity and molecular docking study of thiadiazole bearing isatin analogs

A series of seventeen analogs (1─17) were synthesized and characterized through different spectroscopic techniques such as 1H, 13CNMR, HR-EI-MS and were evaluated for in vitro thymidine phosphorylase inhibition. All compounds showed excellent to good thymidine phosphorylase activity having IC50 value ranging between 4.10 ± 0.20 and 54.60 ± 1.40?μM when compared with standard drug 7-deazaxanthine (IC50 = 38.68 ± 1.12?μM). Among the series, compounds 1 (IC50 = 8.30 ± 0.30?μM), 6 (IC50 = 6.30 ± 0.10?μM), 11 (IC50 = 8.40 ± 0.30?μM) and 16 (IC50 = 4.10 ± 0.20?μM) were found more potent. Potent compounds were further subjected to molecular docking study to identify their interactions with the active site of amino acid. Structure activity relationship was done for all analogs mostly based on substitution pattern on phenyl and isatin rings. Graphic abstract: [Figure not available: see fulltext.]

Thiosemicarbazones exhibit inhibitory efficacy against New Delhi metallo-β-lactamase-1 (NDM-1)

The superbug infection caused by metallo-β-lactamases (MβLs) carrying drug-resistant bacteria, specifically, New Delhi metallo-β-lactamase (NDM-1) has become an emerging threat. In an effort to develop novel inhibitors of NDM-1, thirteen thiosemicarbazones (1a-1m) were synthesized and assayed. The obtained molecules specifically inhibited NDM-1, with an IC50 in the range of 0.88–20.2 μM, and 1a and 1f were found to be the potent inhibitors (IC50 = 1.79 and 0.88 μM) using cefazolin as substrate. ITC and kinetic assays indicated that 1a irreversibly and non-competitively inhibited NDM-1 in vitro. Importantly, MIC assays revealed that these molecules by themselves can sterilize NDM-producing clinical isolates EC01 and EC08, exhibited 78-312-fold stronger activities than the cefazolin. MIC assays suggest that 1a (16 μg ml?1) has synergistic antimicrobial effect with ampicillin, cefazolin and meropenem on E. coli producing NDM-1, resulting in MICs of 4-32-, 4-32-, and 4-8-fold decrease, respectively. These studies indicate that the thiosemicarbazide is a valuable scaffold for the development of inhibitors of NDM-1 and NDM-1 carrying drug-resistant bacteria.

Synthesis and evaluation of novel 1,3,4-thiadiazole–fluoroquinolone hybrids as antibacterial, antituberculosis, and anticancer agents

A series of 5-substituted-1,3,4-thiadiazole-based fluoroquinolone derivatives were designed as potential antibacterial and anticancer agents using a molecular hybridization approach. The target compounds 16–25 were synthesized by reacting the correspondin