| Identification | Back Directory | [Name]
CLORANSULAM-METHYL | [CAS]
147150-35-4 | [Synonyms]
xde-565
CLORANSULAM-METHYL
ChloransulaM-Methyl
cloransulam-methyl (bsi, pa iso, ansi)
Methyl 3-chloro-N-(5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidin-2-ylsulfonyl)anthranilate
Methyl 3-chloro-2-[(5-ethoxy-7-fluoro-[1,2,4]triazolo[5,1-c]pyrimidin-2-yl)sulfonylamino]benzoate
Methyl 3-chloro-2-{[(5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidine-2-yl)sulfonyl]amino}benzoate
3-Chloro-2-[[(5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)sulfonyl]amino]benzoic acid, Methyl ester | [EINECS(EC#)]
405-090-9 | [Molecular Formula]
C15H13ClFN5O5S | [MDL Number]
MFCD08273840 | [MOL File]
147150-35-4.mol | [Molecular Weight]
429.81 |
| Chemical Properties | Back Directory | [Melting point ]
216-218 °C | [density ]
1.538 g/cm3 | [storage temp. ]
0-6°C | [form ]
neat | [pka]
3.97±0.50(Predicted) | [BRN ]
7501727 | [Henry's Law Constant]
1.6×1011 mol/(m3Pa) at 25℃, Ebert et al. (2023) | [InChI]
InChI=1S/C15H13ClFN5O5S/c1-3-27-15-18-10(17)7-11-19-14(20-22(11)15)28(24,25)21-12-8(13(23)26-2)5-4-6-9(12)16/h4-7,21H,3H2,1-2H3 | [InChIKey]
BIKACRYIQSLICJ-UHFFFAOYSA-N | [SMILES]
C(OC)(=O)C1=CC=CC(Cl)=C1NS(C1N=C2C=C(F)N=C(OCC)N2N=1)(=O)=O | [CAS DataBase Reference]
147150-35-4 | [EPA Substance Registry System]
Benzoic acid, 3-chloro-2-[[(5-ethoxy-7-fluoro[ 1,2,4]triazolo[1,5-c]pyrimidin-2-yl)sulfonyl]amino]-, methyl ester(147150-35-4) |
| Hazard Information | Back Directory | [Description]
Cloransulam-methyl is a post-emergence herbicide. It has a moderate aqueous solubility, is non-volatile and, based on its chemical properties, is mobile and may leach to groundwater in some situations. It is generally non- persistent in soil systems but usually degrades quickly in aquatic systems via photolysis. It is not susceptible to hydrolysis. It has a low mammalian toxicity and has a high potential for bioaccumulation. It is a skin and eye irritant. It has a low level of toxicity to birds and aquatic invertebrates but is more toxic to fish, aquatic plants, algae, earthworms and honeybees. | [Uses]
Cloransulam-methyl is a triazolopyrimidine sulfonanilide herbicide. Cloransulam-methyl can be used to control broadleaf weeds in soybean by acetolactate synthase (ALS) inhibition[1]. | [Definition]
ChEBI: The methyl ester of cloransulam. An inhibitor of acetohydroxyacid synthase (AHAS), it prevents the synthesis of amino acids in plants and is used as a herbicide for the control of post-emergence control of broad-leaved weeds in soybeans. It is not approved
for use within the European Area. | [Production Methods]
Cloransulam-methyl is commercially produced through a multi-step organic synthesis designed for large-scale manufacturing, typically involving 5–7 reactions with high yields and minimal waste. The process begins with the construction of the 5-ethoxy-7-fluoro-[1,2,4]triazolo[1,5-c]pyrimidine core from basic heterocyclic precursors like 3-amino-1,2,4-triazole and a suitably substituted pyrimidine derivative via cyclocondensation in the presence of base and solvent (e.g., ethanol or DMF) at elevated temperatures. The 2-sulfonyl chloride intermediate is then formed by chlorosulfonation using chlorosulfonic acid or thionyl chloride. This is followed by nucleophilic coupling with methyl 2-amino-3-chlorobenzoate in a basic medium (e.g., pyridine or triethylamine in dichloromethane) to yield the final sulfonamide product. | [Mechanism of action]
Inhibits plant amino acid synthesis - acetohydroxyacid synthase AHAS. | [Metabolic pathway]
When 14C-cloransulam methyl is incubated with soils,
the degradation proceeds via the hydrolysis of the
ester group and O-de-ethylation on the
triazolopyrimidine ring to yield the three identified
metabolites, cloransulam, 5-hydroxycloransulam
methyl, and 5-hydroxycloransulam. These metabolites
are significantly less phytotoxic than the parent
herbicide. | [References]
[1] Jeffrey D. Wolt, et al. Products and Kinetics of Cloransulam-methyl Aerobic Soil Metabolism. J. Agric. Food Chem. 1996, 44, 1, 324-332. | [Pesticide Type]
Herbicide |
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