731-27-1

Usage

Uses

Used in Agriculture:
TOLYLFLUANID is used as a fungicide for controlling a wide range of fungal diseases on various fruit crops, such as apples, grapes, and strawberries. It helps in protecting these crops from storage diseases, ensuring better yield and quality of the produce.
Used in Analytical Chemistry:
TOLYLFLUANID may be used as a reference standard for the determination of the analyte in nutraceutical formulations. It is employed in combination with dispersive liquid-liquid microextraction (DLLME) coupled with gas chromatography-mass spectrometry method, which aids in accurate analysis and quantification of the target compounds in the samples.

Metabolic pathway

Tolylfluanid contains an unstable dichlorofluoromethylthio (sulfenyl) moiety that has been shown to undergo rapid hydrolytic and metabolic degradation to dimethylaminosulfotoluidide (2). 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 tolylfluanid is probably cleaved at the N-S bond to form thiophosgene or its monofluoro analogue (3) 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, for example addition to cysteine affords thiazolidine-2-thione-4-carboxylica cid (4). A thiazolidine derivative of glutathione may also be formed. The main metabolic reactions in all media were cleavage of the N-S bond to give dimethylaminosulfotoluidide (2) followed by hydroxylation of the phenyl ring and oxidation of the methyl substituent on the phenyl ring. Glucoside conjugates were detected in plants and the cysteine adduct, thiazolidine-2- thione-4-carboxylic acid (4), was formed in rats.

Degradation

Tolylfluanid is hydrolysed rapidly in alkaline conditions. The hydrolytic DT50 is about 12 days, 29 hours and <10 minutes at pH 4,7 and 9, respectively, at 22 °C. In the environment, hydrolysis is faster than photolysis (PM; PSD, 1995). Tolylfluanid does not absorb light of wavelength >295 nm and so photodegradation is unlikely to occur in the absence of photosensitisers.

InChI:InChI=1/C10H13Cl2FN2O2S2/c1-8-4-6-9(7-5-8)15(18-10(11,12)13)19(16,17)14(2)3/h4-7H,1-3H3

Synthetic route

N,N-dimethyl-N'-(4-methylphenyl)-sulfamide (66840-71-9) + dichlorofluoromethanesulphenyl chloride (2712-93-8) → dichloro-N-[(dimethylamino)sulfonyl]fluoro-N-(p-tolyl)methanesulfenamide (731-27-1)

Conditions	Yield
Stage #1: N,N-dimethyl-N'-(4-methylphenyl)-sulfamide With sodium hydride In tetrahydrofuran at 0 - 10℃; Inert atmosphere; Stage #2: dichlorofluoromethanesulphenyl chloride In tetrahydrofuran at 20℃; Reagent/catalyst; Temperature; Inert atmosphere;	17.1 g

N,N-dimethyl-N'-(4-methylphenyl)-sulfamide (66840-71-9) + triethylamine (121-44-8) + dichlorofluoromethanesulphenyl chloride (2712-93-8) → dichloro-N-[(dimethylamino)sulfonyl]fluoro-N-(p-tolyl)methanesulfenamide (731-27-1)

dichloro-N-[(dimethylamino)sulfonyl]fluoro-N-(p-tolyl)methanesulfenamide (731-27-1) → methylamine (74-89-5)

Conditions	Yield
aluminium In water; acetonitrile Product distribution; Irradiation; influence of aluminum foil;;

Upstream product

• 66840-71-9 N,N-dimethyl-N'-(4-methylphenyl)-sulfamide 
• 121-44-8 triethylamine 
• 2712-93-8 dichlorofluoromethanesulphenyl chloride 

Downstream Products

• 74-89-5 methylamine 

Relevant academic research and scientific papers

Synthesis method of high-purity bacteriostatic agent and derivatives thereof

The invention discloses a synthesis method of a high-purity bacteriostatic agent and derivatives thereof. The synthesis method comprises the following specific steps: adding primary amine or secondaryamine into a solvent, adding perchloromethyl mercaptan, reacting at room temperature for 14-18 hours, washing the reaction solution with water, separating, drying, concentrating the solvent and separating to obtain an intermediate 1; mixing the intermediate 1 with a solvent and fluoride, heating to 100-140 DEG C, reacting for 6-18 hours, filtering the reaction solution, washing with water, drying, concentrating the solvent, rectifying and separating to obtain an intermediate 2; mixing the intermediate 2 with a solvent, introducing hydrogen chloride gas at 0-10 DEG C to react for 2-16 hours, washing the reaction solution with water, separating, drying and concentrating the solvent to obtain an intermediate 3; and mixing the intermediate 4 with a solvent, adding alkali at 0-10 DEG C, reacting for 0.5-1 hour, adding the intermediate 3, reacting at room temperature for 1-2 hours, washing the reaction solution with water, separating, drying and concentrating the solvent to obtain the target compound. The method is low in cost and high in product yield and a high-purity product can be obtained.

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.

ACTIVE COMPOUND COMBINATIONS HAVING INSECTICIDAL AND ACARICIDAL PROPERTIES

The novel active compound combinations comprising a compound of the formula (I-1) or (I-2) and the active compounds (1) to (26) listed in the description have very good insecticidal and acaricidal properties.

Fungicidal combinations of active substances

The novel active compound combinations of a fluoro-benzothiazole derivative of the formula and the active compound groups (1) to (51) listed in the description have very good fungicidal properties.

Pyrazolyl benzyl ether derivatives containing a fluoromethoxyimino group and use thereof as pesticides

The invention relates to novel pyrazolyl benzyl ethers, to a plurality of processes for their preparation and to their use for controlling harmful organisms.

Iminoacetic acid amides and their use as pest control agents

PCT No. PCT/EP96/04345 Sec. 371 Date Apr. 15, 1998 Sec. 102(e) Date Apr. 15, 1998 PCT Filed Oct. 7, 1996 PCT Pub. No. WO97/14673 PCT Pub. Date Apr. 24, 1997Iminoacetamides of the formula (I) in which A represents a single bond or optionally substituted alkylene, Q represents oxygen or sulphur, R1 represents respectively optionally substituted cycloalkyl, cycloalkenyl, aryl or heterocyclyl, R2 represents respectively optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, aryl or heterocyclyl, R3 represents hydrogen or respectively optionally substituted alkyl, alkenyl, alkinyl or cycloalkyl, R4 represents respectively optionally substituted cycloalkyl, cycloalkenyl, aryl or heterocyclcyl a process for their preparation, pesticidal compositions containing them, and their use for controlling pests.

Microbicidal benzotriazoles

Novel benzotriazoles of the formula STR1 in which R, X1, X2, X3, X4 and Y have the meanings given in the description, and their acid addition salts and metal salt complexes, a process for the preparation of these substances and their use as microbicides in crop protection and in material protection.

Halogen alkenyl azolyl microbicides

Novel halogenoalkenyl-azolyl derivatives of the formula STR1 in which R1 represents optionally substituted alkyl, optionally substituted alkenyl, optionally substituted cycloalkyl, optionally substituted aryl or represents optionally substituted heteroaryl, R2 represents alkyl, halogenoalkyl, 1-hydroxyalkyl, 2-hydroxyalkyl, 1-hydroxyhalogenalkyl, 1-alkenyl or 2-alkenyl, X1 represents fluorine, chlorine, bromine or iodine, X2 represents fluorine, chlorine, bromine or iodine, and Y represents nitrogen or a CH group, and addition products thereof with acids or metal salts are very active as microbicides in plant protection and in the protection of materials.

Acylated 5-aminopyrazoles and the use thereof to combat animal parasites

The present invention relates to new acylated 5-aminopyrazoles of the formula (I) STR1 in which R1, R2, R3, R4 and R5 have the meaning given in the description, to processes for their preparation and to their use as pesticides.