DICHLOFLUANID CAS 1085-98-9
Introduction：Basic information about DICHLOFLUANID CAS 1085-98-9, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
DICHLOFLUANID Basic information
| Product Name: | DICHLOFLUANID |
| Synonyms: | 1,1-dichloro-n-[(dimethylamino)sulfonyl]-1-fluoro-n-phenyl-methanesulfenamid;dichlofluanid (bsi,iso);dichlofluanid solution;dichlorfluanid (jmaf);N,N-Dimethyl-N-[(dichlorofluoromethyl)thio-N-phenylsulfamide;dichlofluanid (ISO) N-dichlorofluoromethylthio-N',N'-dimethyl-N-phenylsulphamide;DICHLOFLUANID PESTANAL, 250 MG;DICHLOFLUANID, 1GM, NEAT |
| CAS: | 1085-98-9 |
| MF: | C9H11Cl2FN2O2S2 |
| MW: | 333.23 |
| EINECS: | 214-118-7 |
| Product Categories: | Organics;AcaricidesPesticides;Alpha sort;Amide structurePesticides&Metabolites;D;DAlphabetic;DIA - DIC;Fungicides;Pesticides;Pesticides&Metabolites;Amide structureAlphabetic |
| Mol File: | 1085-98-9.mol |
DICHLOFLUANID Chemical Properties
| Melting point | 110-112℃ (ethanol ) |
| Boiling point | 154°C (rough estimate) |
| density | 1.5752 (rough estimate) |
| vapor pressure | 1.5 x 10-5 Pa (20 °C) |
| refractive index | 1.6000 (estimate) |
| Fp | 2 °C |
| storage temp. | APPROX 4°C |
| Water Solubility | 1.3 mg l-1 (20 °C) |
| pka | -5.37±0.50(Predicted) |
| Merck | 13,3070 |
| BRN | 2947992 |
| Major Application | agriculture environmental |
| InChI | 1S/C9H11Cl2FN2O2S2/c1-13(2)18(15,16)14(17-9(10,11)12)8-6-4-3-5-7-8/h3-7H,1-2H3 |
| InChIKey | WURGXGVFSMYFCG-UHFFFAOYSA-N |
| SMILES | CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)c1ccccc1 |
| CAS DataBase Reference | 1085-98-9 |
| EPA Substance Registry System | Dichlofluanid (1085-98-9) |
Safety Information
| Hazard Codes | Xn,N,F |
| Risk Statements | 20-36-43-50/53-20/21/22-11-50 |
| Safety Statements | 24-37-60-61-36-26-16-36/37 |
| RIDADR | 2588 |
| WGK Germany | 3 |
| RTECS | WO6475000 |
| HazardClass | 6.1(b) |
| PackingGroup | III |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Inhalation Aquatic Acute 1 Eye Irrit. 2 Skin Sens. 1 |
| Hazardous Substances Data | 1085-98-9(Hazardous Substances Data) |
| Toxicity | LD50 in rats, guinea pigs, rabbits (mg/kg): 1.000 orally in all species (Grewe) |
| Description | Dichlofluanid is solid sparingly soluble inwater, soluble in most organic solvents, and decomposesin alkaline media. |
| Chemical Properties | White powder. Melting point 105-106°C, vapor pressure 0.133×10-6kPa at 20°C, insoluble in water, soluble in acetone, methanol (15g/L), xylene (70g/L), light-sensitive, decomposed in strong alkali. |
| Uses | Fungicide. |
| Uses | Dichlofluanid is used to control a wide range of fungal diseasesincluding storage diseases on many crops. |
| Definition | ChEBI: A member of the class of sulfamides that is sulfamide in which the hydrogens attached to one of the nitrogens are replaced by methyl groups, while those attached to the other nitrogen are replaced by a phenyl and a [dichloro(fluoro)methyl]sulfanediyl group A fungicide introduced in 1965 and used in the cultivation of fruit and vegetables, as well as in wood preservatives, it is no longer approved for use in the European Union. |
| Metabolic pathway | Dichlofluanid contains an unstable dichlorofluoromethylthio (sulfenyl)moiety that has been shown to undergo rapid hydrolytic and metabolicdegradation to N',N'-dimethyl-N-phenylsulfamide (2) (dimethylsulfanilide).By analogy with captan, presumably the dichlorofluoromethylthiomoiety can be transferred to the sulfur atoms of cellular thiols such ascysteine and glutathione. Thus in the presence of thiols, dichlofluanidis probably cleaved at the N-S bond to form thiophosgene (3) orits monofluoro analogue and other gaseous products such as hydrogensulfide, hydrogen chloride and carbonyl sulfide. Thiophosgene or itsmonofluoro analogue is rapidly hydrolysed by water. The dichlorofluoromethylthiogroup and thiophosgene may be intermediates in theformation of addition products such as thiazolidine-2-thione-4-carboxylicacid (4) by addition to cysteine. A thiazolidine derivative of glutathionemay also be formed (5). |
| Degradation | Dichlofluanid is hydrolysed rapidly in alkaline conditions to form N',N'-dimethyl-N-phenylsulfamide (2). The hydrolytic DT50 is >15 days, >18hours and <10 minutes at pH 4,7 and 9, respectively, at 22 °C (PM). Dichlofluanid is unstable to light and its fungitoxicity decreases onexposure, albeit to a lesser extent than for captan. Dichlofluanid does notabsorb light of wavelength of >295 nm and so photodegradation isunlikely to occur in the absence of photosensitisers. Dichlofluanid wasreacted in vitru with glutathone or cysteine in water/methanol solutions.The reaction was carried out in a closed system at 40 °C using traps forCOS and CO2 and analysis by TLC. The proposed route of degradationis given in Scheme 1. Short-lived intermediates are proposed that werenot detected. It is not clear whether thiophosgene (3) or its monofluoroanalogue were formed (Schuphan ef al., 1981). The photolysis of dichlofluanid was studied under artificial conditionsthat may not be relevant to typical environmental circumstances.Unlabelled dichlofluanid in methanol, benzene or acetone solution wasirradiated with a medium pressure UV lamp (100 W) but the emissionwavelengths were not given. As they photodegraded, the methanoland benzene solutions gave a brown solid and the acetone solutiondarkened. Products were separated and identified using IR, GC and MSmethods. The products from acetone solution were N',N'-dimethyl-Nphenylsulfamide(2), phenyl isocyanate (6), phenyl isothiocyanate (7) anddimethylamidosulfonyl chloride (8). Studies using GC-MS indicated thepresence of bis(dichlorofluoromethyl) disulfide (9). It was concluded thatirradiation of dichlofluanid produced mainly the hydrolysis productdimethylsulfanilide (2) and the very active dichlorofluoromethyl sulfide radical (.SCCl2F), the latter reacting with other compounds in solution. For example, 1-(dichlorofluoromethylthio)propan-2-one (10), and 1-(dichlorofluoromethylsulfonyl)propan-2-one(11) were formed in acetonesolution by reaction with solvent. The phenyl isothiocyanate (12) was alsoisolated In vitro tests against Botrytis cinerea showed that irradiationdecreased the fungicidal activity of dichlofluanid (Clark and Watkins,1978). |
DICHLOFLUANID Preparation Products And Raw materials
| Raw materials | DICHLOROFLUOROMETHANESULFENYL CHLORIDE-->DMSA-->Triethylamine-->Aniline |
