Acibenzolar-S-Methyl

Base Information

• Chemical Name: Acibenzolar-S-Methyl
• CAS No.: 135158-54-2
• Molecular Formula: C8H6N2OS2
• Molecular Weight: 210.28
• European Community (EC) Number: 420-050-0,603-901-2
• UNII: BCW6119347
• DSSTox Substance ID: DTXSID1032519
• Nikkaji Number: J737.150K
• Wikipedia: Acibenzolar-S-methyl
• Wikidata: Q341312
• Metabolomics Workbench ID: 66292
• ChEMBL ID: CHEMBL425055
• Mol file: 135158-54-2.mol

Synonyms:acibenzolar-S-methyl;benzo(1,2,3)thiadiazole-7-carbothioic acid S-methyl ester;BTH ester;GGA 245704;S-methyl benzo(1,2,3)thiadiazole-7-carbothioate

Chemical Property of Acibenzolar-S-Methyl

Chemical Property:

• Appearance/Colour: Beige fine powder
• Vapor Pressure: 4.4 x 10-4 Pa (25 °C)
• Melting Point: 132.9oC
• Refractive Index: 1.5690 (estimate)
• Boiling Point: 331.8 °C at 760 mmHg
• PKA: -3.90±0.50(Predicted)
• Flash Point: 154.5 °C
• PSA: 111.41000
• Density: 1.45 g/cm³
• LogP: 2.72980
• Storage Temp.: 0-6°C
• Solubility.: Chloroform (Slightly), Methanol (Very Slightly)
• Water Solubility.: 7.7 mg l-1 (25 °C)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 209.99215517
• Heavy Atom Count: 13
• Complexity: 212

Purity/Quality:

99.9% ^*data from raw suppliers

Acibenzolar-S-methyl ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,N
• Hazard Codes: Xi,N
• Statements: 36/37/38-43-50/53
• Safety Statements: 24/25-37-46-59-60-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Herbicides, Other
• Canonical SMILES: CSC(=O)C1=C2C(=CC=C1)N=NS2
• Description: Acibenzolar-S-methyl (Novartis) has attracted special attention because it acts against a very wide range of plant diseases but does not directly affect the growth or metabolism of the causal organisms. It is known to act by stimulating systemic activated resistance (SAR) in the treated plant. The well-established compound probenazole, which for some years has been the leading treatment for rice blast in Japan, is thought to act in a similar way. Pathogen resistance to probenazole has not developed, and such stability of performance may well be a general feature of SAR-inducing compounds.
• Uses: Acibenzolar-S-methyl is a S-methyl thioester derivative of acibenzolar. Acibenzolar-S-Methyl acts as a fungicide in pesticidal formulations. Plant disease resistance activator. CGA245704 is used to control a range of diseases in wheat and it is being developed for use on rice, bananas, vegetables and tobacco.

Technology Process of Acibenzolar-S-Methyl

There total 19 articles about Acibenzolar-S-Methyl 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:

Lawessons reagent (19172-47-5,94367-93-8) + benzo-1,2,3-thiadiazole-7-thiomethyl ester → S-methyl-benzo[1,2,3]thiadiazole-7-carbothioate (135158-54-2)

Guidance literature:

In 5,5-dimethyl-1,3-cyclohexadiene;

Reference yield:

benzo[d][1,2,3]thiadiazole-7-carboxylic acid (35272-27-6) → S-methyl-benzo[1,2,3]thiadiazole-7-carbothioate (135158-54-2)

Guidance literature:

Multi-step reaction with 2 steps

1: SOCl₂ / 8 h / 90 °C

2: 0.12 g / CH₂Cl₂ / 5 h / 20 °C

With thionyl chloride; In dichloromethane;

DOI:10.1021/jf0618574

Reference yield:

2-chloro-3-nitrobenzoic acid methyl ester (53553-14-3) → S-methyl-benzo[1,2,3]thiadiazole-7-carbothioate (135158-54-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 99 percent

2: H₂ / Raney nickel / tetrahydrofuran

3: 86 percent / NaNO₂; H(+)

4: 98 percent / NaOH; H₂O

5: SOCl₂

With sodium hydroxide; thionyl chloride; water; hydrogen; hydrogen cation; sodium nitrite; nickel; In tetrahydrofuran; 1: Substitution / 2: Reduction / 3: Diazotization / 4: Hydrolysis / 5: Substitution / 6: Esterification;

DOI:10.1002/(SICI)1096-9063(199708)50:4<275::AID-PS593>3.0.CO;2-7

upstream raw materials:

methylthiol

benzothiadiazole-7-carboxylic acid chloride

sodium thiomethoxide

benzo[d][1,2,3]thiadiazole-7-carboxylic acid

Refernces

• 1、 -. "Synergistic Combinations Of Active Ingredients". . . Retrieved 2012/02/15.
• 2、 Zhu, Weiping,Zhao, Zhenjiang,Xu, Yufang. "Derivatives of benzothiadiazole-7-carboxylates: Synthesis and biological activity". scheme or table. p. 1067 - 1071. Retrieved 2009/12/02.