5-(4-chlorophenyl)-N-cyclohexyl-4-methyl-2-oxo-1,3-thiazolidine-3-carboxamide

Base Information

• Chemical Name: 5-(4-chlorophenyl)-N-cyclohexyl-4-methyl-2-oxo-1,3-thiazolidine-3-carboxamide
• CAS No.: 78587-05-0
• Molecular Formula: C₁₇H₂₁ClN₂O₂S
• Molecular Weight: 352.885
• Hs Code.: 29341000
• DSSTox Substance ID: DTXSID70861009
• Nikkaji Number: J3.005.230G
• Mol file: 78587-05-0.mol

Synonyms:5-(4-chlorophenyl)-N-cyclohexyl-4-methyl-2-oxothiazolidine-3 carboxamide;hexythiazox

Chemical Property of 5-(4-chlorophenyl)-N-cyclohexyl-4-methyl-2-oxo-1,3-thiazolidine-3-carboxamide

Chemical Property:

• Appearance/Colour: light tan granules with a faint ligneous odor
• Melting Point: 108-108.5 °C
• Refractive Index: 1.621
• Boiling Point: 128°C (rough estimate)
• PKA: 12.77±0.20(Predicted)
• Flash Point: 100°C
• PSA: 74.71000
• Density: 1.31 g/cm³
• LogP: 5.30950
• Storage Temp.: 0-6°C
• Water Solubility.: 0.5mg/L
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 352.1012268
• Heavy Atom Count: 23
• Complexity: 448

Purity/Quality:

99% ^*data from raw suppliers

Hexythiazox ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Pesticides -> Other Insecticides
• Canonical SMILES: CC1C(SC(=O)N1C(=O)NC2CCCCC2)C3=CC=C(C=C3)Cl
• Uses: It belongs to thiazolidone acaricide. This product has broad insecticidal spectrum and high acaricidal activities on spider mite, mocking mite, and panonychus citri. It has good effects in the use of low concentrations and better residual effects. It has no cross resistance problems with organophosphorus, dicofol and so on. It is safe for crops and beneficial insects feeding on mites with main contact effects. It has good penetration to the epidermis of plants, poor effect on adults but no inner-absorption conduction. It has a strong killing effect on many kinds of plant mites with the characteristics of killing young nymphs, but it is ineffective against adult mites. The eggs produced by female mites exposed to liquid medicine are inhibited. The effect is slow, but the residual effect can last as long as more than one month. Like the prevention and treatment of apple red spiders, during full incidence period of young nymphs, if there are 3 to 4 mites per leaf on average, 5 % EC or 5 % WP can be sprayed in 1500～2000 times. Stop using it at least 7 days before the harvest. Hexythiazox is a mite growth regulator and a thiazolidine based acaricide that has long-lasting effects against many kinds of mites and is applied at any stage of the plant growth from budding to frui ting. Nonsystemic acaricide.
• Description: Hexythiazox is an acaricide that induces toxicity in larvae of the two-spotted spider mite T. urticae and the European red mite P. ulmi (LC50s = 0.15-0.58 and 0.23-0.62 mg AI/L, respectively), as well as in the summer and winter eggs of P. ulmi (LC50s = 2.2 and 20 ppm, respectively). Hexythiazox is toxic to bluegill (L. macrochirus; LC50 = 3.2 mg/L) and D. magna (EC50 = 0.36 mg/L) but not rats (LD50 = >5,000 mg/kg). Formulations containing hexythiazox have been used in the control of mites in agriculture.

Technology Process of 5-(4-chlorophenyl)-N-cyclohexyl-4-methyl-2-oxo-1,3-thiazolidine-3-carboxamide

There total 7 articles about 5-(4-chlorophenyl)-N-cyclohexyl-4-methyl-2-oxo-1,3-thiazolidine-3-carboxamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

5-(4-chlorophenyl)-4-methyl-2-oxo-thiazolidin + Cyclohexyl isocyanate (3173-53-3) → N-cyclohexyl-(4RS,5RS)-5-(4-chlorophenyl)-4-methyl-2-oxo-1,3-thiazolidine-3-carboxamide (78587-05-0)

Guidance literature:

With N,N-diethylaniline; In toluene; at 55 - 60 ℃; Reagent/catalyst;

Reference yield:

trans-4-methyl-5-(4-chlorophenyl)-2-thiazolidone (87827-96-1) + Cyclohexyl isocyanate (3173-53-3) → trans-5-(4-chlorophenyl)-N-cyclohexyl-4-methyl-2-oxo-3-thiazolidine-carboxamide (78587-05-0)

Guidance literature:

In dimethyl sulfoxide;

Reference yield:

4'-chloropropiophenone (6285-05-8) → N-cyclohexyl-(4RS,5RS)-5-(4-chlorophenyl)-4-methyl-2-oxo-1,3-thiazolidine-3-carboxamide (78587-05-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: n-Butyl nitrite / Petroleum ether / 5 h

2.1: platinum / methanol / 0.5 h / Inert atmosphere

2.2: 35 °C / 225.02 Torr

2.3: 1 h / 40 °C / pH 6

3.1: carbon disulfide; potassium hydroxide; sodium methylate / water / 12 h / 80 °C

4.1: sodium peroxide / methanol / 0.5 h

4.2: 6 h / 20 - 25 °C

5.1: triethylamine / toluene / 8 h / 37 °C

With carbon disulfide; sodium peroxide; n-Butyl nitrite; sodium methylate; triethylamine; platinum; potassium hydroxide; In methanol; water; toluene; Petroleum ether;

upstream raw materials:

trans-4-methyl-5-(4-chlorophenyl)-2-thiazolidone

Cyclohexyl isocyanate

4'-chloropropiophenone

1-(4-chlorophenyl)-2-(hydroxyimino)propan-1-one

Refernces

• 1、 -. "Hexythiazox and preparation method thereof". . . Retrieved 2017/08/24.
• 2、 -. "1,3,4-oxadiazine derivatives and their use as pesticides". . . Retrieved 2008/06/13.