1085-98-9

Basic information

• Product Name: DICHLOFLUANID
• Synonyms: 1,1-dichloro-n-[(dimethylamino)sulfonyl]-1-fluoro-n-phenyl-methanesulfenamid;1,1-Dichloro-N’-[(dimethylamino)sulfonyl]-1-fluoro-N-phenylmethanesulfenamide;Aniline, N-((dichlorofluoromethyl)thio)-N-((dimethylamino)sulfonyl)-;BAY 47531;bay47531;Bayer 47531;bayer47531;Dichlofluanide
• CAS NO: 1085-98-9
• Molecular Formula: C₉H₁₁Cl₂FN₂O₂S₂
• Molecular Weight: 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

Chemical Properties

• Melting Point: 110-112℃ (ethanol )
• Boiling Point: 154°C (rough estimate)
• Flash Point: 2 °C
• Appearance: /
• Density: 1.5752 (rough estimate)
• Vapor Pressure: 0.00011mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: APPROX 4°C
• PKA: -5.37±0.50(Predicted)
• Water Solubility: 1.3 mg l-1
• Merck: 13,3070
• BRN: 2947992
• CAS DataBase Reference: DICHLOFLUANID(CAS DataBase Reference)
• NIST Chemistry Reference: DICHLOFLUANID(1085-98-9)
• EPA Substance Registry System: DICHLOFLUANID(1085-98-9)

Safety Data

• Hazard Codes: Xn,N,F
• 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
• Hazardous Substances Data: 1085-98-9(Hazardous Substances Data)

Usage

Uses

Used in Agriculture:
Dichlofluanid is used as a fungicide for controlling a wide range of fungal diseases, including storage diseases on many crops. Its application helps protect plants from infections and ensures a healthy growth, leading to increased crop yields.
Used in Wood Preservation:
Dichlofluanid was also used in wood preservatives to protect wood from fungal infections and decay. This application helped extend the lifespan of wooden structures and materials, reducing the need for frequent replacements and maintenance.

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).

InChI:InChI=1/C9H11Cl2FN2O2S2/c1-13(2)18(15,16)14(17-9(10,11)12)8-6-4-3-5-7-8/h3-7H,1-2H3

Synthetic route

N,N-dimethyl-N'-phenylsulfonamide (4710-17-2) + dichlorofluoromethanesulphenyl chloride (2712-93-8) → N-dichlorofluoromethylthio-N',N'-dimethyl-N-phenylsulfamide (1085-98-9)

Conditions	Yield
Stage #1: N,N-dimethyl-N'-phenylsulfonamide With sodium hydride In toluene at 0 - 20℃; for 1h; Stage #2: dichlorofluoromethanesulphenyl chloride In toluene at 20℃;	84.2%

N,N-dimethyl-N'-phenylsulfonamide (4710-17-2) + triethylamine (121-44-8) + dichlorofluoromethanesulphenyl chloride (2712-93-8) → N-dichlorofluoromethylthio-N',N'-dimethyl-N-phenylsulfamide (1085-98-9)

N-dichlorofluoromethylthio-N',N'-dimethyl-N-phenylsulfamide (1085-98-9) → bis(dichlorofluoromethyl)disulfane (675-63-8)

Conditions	Yield
In acetone Irradiation (UV/VIS); together with other products;
In acetone Irradiation (UV/VIS); together with other products;

Upstream product

• 4710-17-2 N,N-dimethyl-N'-phenylsulfonamide 
• 121-44-8 triethylamine 
• 2712-93-8 dichlorofluoromethanesulphenyl chloride 

Related news

Monitoring of the booster biocide DICHLOFLUANID (cas 1085-98-9) in water and marine sediment of Greek marinas08/14/2019

Dichlofluanid (N-dichlorofluoromethylthio-N′-dimethyl-N-phenylsulphamide) is used as booster biocide in antifouling paints. The occurrence of dichlofluanid and its metabolite DMSA (N′-dimethyl-N-phenyl-sulphamide) was monitored in seawater and marine sediment from three Greek marinas. Seawater...detailed

Relevant articles and documents

N, N-dimethyl-N-phenyl-(N- fluorine two chlorine armor thio)-sulfonaide synthesis process

The invention discloses a process for synthesizing N,N-dimethyl-N-phenyl-(N-fluorodichloromethylmercapto)-sulfamide. The synthesis process comprises the following steps: by taking ferric fluoride as a fluoride, recrystallizing a toluene solution of fluorodichloromethylsulfuryl chloride and N,N-dimethyl-N'-phenyl sulfamide under a certain reaction conditions so as to prepare the N,N-dimethyl-N-phenyl-(N-fluorodichloromethylmercapto)-sulfamide. According to the synthesis process, an intermediate is synthesized, the utilization rate and yield of the intermediate can be improved in the intermediate preparation process, the residual substances are conveniently recycled after the reaction, the cost is greatly saved, and the environmental pollution is reduced. The ferric fluoride is taken as the fluoride in the intermediate synthesis process, so that the yield of the N,N-dimethyl-N-phenyl-(N-fluorodichloromethylmercapto)-sulfamide is improved, the influence on the environment is slight, and the problems that the N,N-dimethyl-N-phenyl-(N-fluorodichloromethylmercapto)-sulfamide is difficultly produced industrially because the raw material cost is high, the generated three industrial wastes have great damage to the environment and the yield is low and instable in the conventional method and the like are solved.

Synergistic Combinations Of Active Ingredients

The present invention relates to novel active compound combinations comprising, firstly, at least one known compound of the formula (I) in which R1 and A have the meanings given in the description and, secondly, at least one further known active compound from groups (2) to (27) listed in the description, which combinations are highly suitable for controlling animal pests such as insects and unwanted acarids and also phytopathogenic fungi.

Synergistic Active Compound Combinations Comprising Phenyltriazoles

The present invention relates to novel active compound combinations comprising, firstly, at least one known compound of the formula (I) in which R1 and R2 have the meanings given in the description. and at least one further known active compound from groups (2) to (27) listed in the description, which combinations are highly suitable for controlling animal pests such as insects and unwanted acarids and also phytopathogenic fungi.

Preservative for aqueous products and systems

An antimicrobial composition for preserving products or systems containing an aqueous phase comprising from 10 to 60% by weight or tert.-butyl hydroperoxide, from 3 to 50% by weight of a monophenylglycol ether of formulas I or II herein, and the remainder a diluent which is water, an organic solvent or a mixture of water and organic solvent; and a method of use of the antimicrobial composition. The antimicrobial composition may additionally include up to about 20% by weight of a biocide selected from certain non-halogenated phenols, certain heterocyclic compounds and guanidine, phthalimide and urea derivatives.

Organosilyl compounds and their use as fungicides

Organosilyl compounds of the general formula I STR1 where R1, R2 and R3 are alkyl, substituted alkyl, alkenyl, alkynyl, cycloalkyl, phenyl or substituted aryl, R4 and R5 are alkyl or hydrogen and Y is CH2, oxygen, nitrogen or alkyl-substituted nitrogen, their salts and fungicides containing these compounds.

Pesticidal compositions containing phosphoric esters and divalent sulphur compounds

Pesticidal composition comprising: a pesticidal, phosphoric ester the molecule of which has at least one alkyl group of 1 to 3 carbon atoms, 0.05 to 10% of an agent stabilizing the said ester against decomposition by protonisation, together with adjuvants characterized in that the stabilizing agent comprises at least one sulphur compound containing per molecule at least one divalent sulphur atom of which one valence is bonded to an atom chosen from sulphur, carbon, nitrogen, hydrogen, and metals capable of giving a salt, the other valence being bonded to an atom chosen from hydrogen, the carbon atom already noted, a second carbon atom, the nitrogen atom already noted, a second nitrogen atom, the metal atom already noted in the case of a metal of valence greater than one, a second atom of metal and oxygen when the first valence is not attached to an atom of hydrogen, the proportion of sulphur calculated with reference to the weight of the sulphur compound being between 5 and 99%. Process for stabilizing a phosphoric ester of which the molecule possesses at least one alkyl group containing 1 to 3 carbon atoms characterized in that there is added to the phosphoric ester or to a mixture which contains it, 0.05 to 10% calculated on the weight of the phosphoric acid ester of an agent capable of stabilizing the said phosphoric ester against protonisation and comprising at least one sulphur compound such as that defined thereupon.