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DICHLOFLUANID

CAS No.
1085-98-9
Chemical Name:
DICHLOFLUANID
Synonyms
rman);Eparen;B-47531;ELVARON;Oiparen;Pecudin;EUPAREN;diparen;bay47531;Euparene
CBNumber:
CB0734712
Molecular Formula:
C9H11Cl2FN2O2S2
Molecular Weight:
333.23
MDL Number:
MFCD00078639
MOL File:
1085-98-9.mol
Last updated:2023-04-23 13:52:06

DICHLOFLUANID 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)
Flash point 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
CAS DataBase Reference 1085-98-9
EWG's Food Scores 3
FDA UNII 76A92XU36Y
EPA Substance Registry System Dichlofluanid (1085-98-9)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS07,GHS09
Signal word  Warning
Hazard statements  H317-H319-H332-H400
Precautionary statements  P261-P273-P280-P302+P352-P304+P340+P312-P305+P351+P338
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
Toxicity LD50 in rats, guinea pigs, rabbits (mg/kg): 1.000 orally in all species (Grewe)

DICHLOFLUANID price More Price(6)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich CRM04195 Dichlofluanid certified reference material, TraceCERT? 1085-98-9 100MG $89.3 2024-03-01 Buy
Sigma-Aldrich 45433 Dichlofluanid PESTANAL 1085-98-9 250mg $52.5 2024-03-01 Buy
TRC D434513 Dichlofluanid 1085-98-9 25mg $80 2021-12-16 Buy
Usbiological 446661 Dichlofluanid 1085-98-9 25mg $355 2021-12-16 Buy
American Custom Chemicals Corporation AGR0000168 DICHLOFLUANID 98.00% 1085-98-9 5G $1155 2021-12-16 Buy
Product number Packaging Price Buy
CRM04195 100MG $89.3 Buy
45433 250mg $52.5 Buy
D434513 25mg $80 Buy
446661 25mg $355 Buy
AGR0000168 5G $1155 Buy

DICHLOFLUANID Chemical Properties,Uses,Production

Description

Dichlofluanid is solid sparingly soluble in water, soluble in most organic solvents, and decomposes in alkaline media.

Uses

Dichlofluanid is used to control a wide range of fungal diseases including storage diseases on many crops.

Uses

Fungicide.

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 metabolic degradation to N',N'-dimethyl-N-phenylsulfamide (2) (dimethylsulfanilide). By analogy with captan, presumably the dichlorofluoromethylthio moiety can be transferred to the sulfur atoms of cellular thiols such as cysteine and glutathione. Thus in the presence of thiols, dichlofluanid is probably cleaved at the N-S bond to form thiophosgene (3) or its monofluoro analogue and other gaseous products such as hydrogen sulfide, hydrogen chloride and carbonyl sulfide. Thiophosgene or its monofluoro analogue is rapidly hydrolysed by water. The dichlorofluoromethylthio group and thiophosgene may be intermediates in the formation of addition products such as thiazolidine-2-thione-4-carboxylic acid (4) by addition to cysteine. A thiazolidine derivative of glutathione may 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, >18 hours and <10 minutes at pH 4,7 and 9, respectively, at 22 °C (PM).
Dichlofluanid is unstable to light and its fungitoxicity decreases on exposure, albeit to a lesser extent than for captan. Dichlofluanid does not absorb light of wavelength of >295 nm and so photodegradation is unlikely to occur in the absence of photosensitisers. Dichlofluanid was reacted in vitru with glutathone or cysteine in water/methanol solutions. The reaction was carried out in a closed system at 40 °C using traps for COS and CO2 and analysis by TLC. The proposed route of degradation is given in Scheme 1. Short-lived intermediates are proposed that were not detected. It is not clear whether thiophosgene (3) or its monofluoro analogue were formed (Schuphan ef al., 1981).
The photolysis of dichlofluanid was studied under artificial conditions that may not be relevant to typical environmental circumstances. Unlabelled dichlofluanid in methanol, benzene or acetone solution was irradiated with a medium pressure UV lamp (100 W) but the emission wavelengths were not given. As they photodegraded, the methanol and benzene solutions gave a brown solid and the acetone solution darkened. Products were separated and identified using IR, GC and MS methods. The products from acetone solution were N',N'-dimethyl-Nphenylsulfamide (2), phenyl isocyanate (6), phenyl isothiocyanate (7) and dimethylamidosulfonyl chloride (8). Studies using GC-MS indicated the presence of bis(dichlorofluoromethyl) disulfide (9). It was concluded that irradiation of dichlofluanid produced mainly the hydrolysis product dimethylsulfanilide (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 acetone solution by reaction with solvent. The phenyl isothiocyanate (12) was also isolated In vitro tests against Botrytis cinerea showed that irradiation decreased the fungicidal activity of dichlofluanid (Clark and Watkins, 1978).

4710-17-2
2712-93-8
1085-98-9
Synthesis of DICHLOFLUANID from DMSA and DICHLOROFLUOROMETHANESULFENYL CHLORIDE

DICHLOFLUANID Preparation Products And Raw materials

Raw materials

Preparation Products

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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 DICHLOROFLUANIDE B-47531 N-(Dichlorofluoromethylthio)-N-(dimethylaminosulfonyl)aniline [[dichloro(fluoro)methyl]thio]-(dimethylsulfamoyl)-phenyl-amine N-[dichloro(fluoro)methyl]sulfanyl-N-(dimethylsulfamoyl)aniline Dichlofluanid 1g [1085-98-9] Diclofluanide Euparen WG Lichenicide 246 N-DICHLOROFLUOROMETHYLTHIO-N',N'-DIMETHYL-N-PHENYLSULFAMIDE N-[(DICHLOROFLUOROMETHYL)THIO]-N',N'-DIMETHYL-N-PHENYLSULPHAMIDE ELVARON 1,1-dichloro-n-((dimethylamino)sulfonyl)-1-fluoro-n-phenyl-methanesulfenamid 1,1-Dichloro-N-((dimethylamino)sulfonyl)-1-fluoro-N-phenylmethanesulfenamide n-dichlorfluormethylthio-n’,n’-dimethylaminosulfonsaeureanilid Oiparen Pecudin rman) Sulfamide, N-[(dichlorofluoromethyl)thio]-N',N'-dimethyl-N-phenyl- DICHLOFLUANID Dichlofluanid emulsion(content>25%) EUPAREN(R) EUPAREN 1,1-Dichloro-N’-[(dimethylamino)sulfonyl]-1-fluoro-N-phenylmethanesulfenamide Aniline, N-((dichlorofluoromethyl)thio)-N-((dimethylamino)sulfonyl)- BAY 47531 bay47531 Bayer 47531 bayer47531 Dichlofluanide dichlorfluanid Diclofluanid diparen Eparen Euparene Ku 13-o32-c ku13-032-c ku13-o32-c Kue 13032c kue13032c Methanesulfenamide, 1,1-dichloro-N-[(dimethylamino)sulfonyl]-1-fluoro-N-phenyl- n-((dichlorofluoromethyl)thio)-n-((dimethylamino)sulfonyl)-anilin n-((dichlorofluoromethyl)thio)-n’,n’-dimethyl-n-phenyl-sulfamid N-([Dichloro(fluoro)methyl]sulfanyl)-N',N'-dimethyl-N-phenylsulfamide N-(Dichlor-fluor-methyl-thio)-N',N'-dimethyl-N-phenyl-schwefel-saeurediamid n-(dichlor-fluor-methyl-thio)-n’,n’-dimethyl-n-phenyl-schwefel-saeurediamid n-(dichlor-fluor-methyl-thio)-n’,n’-dimethyl-n-phenyl-schwefel-saeurediamid(ge n-(dichlorofluoromethylthio)-n-(dimethylsulfamoyl)-aniline n,n-dimethyl-n’-phenyl-n’-fluorodichloromethylthiosulfamide N,N-Dimethyl-N'-phenyl-N'-((fluorodichloromethyl)thio)sulfamide