85509-19-9

Basic information

• Product Name: Flusilazole
• Synonyms: (bis(4-fluorophenyl))(methyl)(1h-1,2,4-triazol-1-ylmethyl)-silan;4-triazole,1-((bis(4-fluorophenyl)methylsilyl)methyl)-1h-2;dpx-h6573;flusilazol;fluzilazol;SANCTION;PUNCH;PUNCH(R)
• CAS NO: 85509-19-9
• Molecular Formula: C₁₆H₁₅F₂N₃Si
• Molecular Weight: 315.39
• Product Categories: Fungicide;Special Silanes;ConazolesAlphabetic;Alpha sort;ConazolesPesticides&Metabolites;E-GAlphabetic;F;FA - FL;Fungicides;Pesticides
• Mol File: 85509-19-9.mol

Chemical Properties

• Melting Point: 55°
• Boiling Point: 393 °C [760mmHg]
• Flash Point: 192°C
• Appearance: brown-red viscous liquid
• Density: 1.17
• Vapor Pressure: 1.2E-07mmHg at 25°C
• Refractive Index: 1.563
• Storage Temp.: 0-6°C
• PKA: 2.5 at 25℃
• Water Solubility: 900 mg l-1 (pH 1.1), 50 mg l-1 (pH 5.7), 45 mg l-1 (pH 7.8) at 25 °C
• Merck: 13,4232
• BRN: 5824097
• CAS DataBase Reference: Flusilazole(CAS DataBase Reference)
• NIST Chemistry Reference: Flusilazole(85509-19-9)
• EPA Substance Registry System: Flusilazole(85509-19-9)

Safety Data

• Hazard Codes: T;N,N,T
• Statements: 61-22-40-51/53
• Safety Statements: 53-45-61
• RIDADR: UN 2588
• WGK Germany: 3
• RTECS: XZ4105000
• Hazardous Substances Data: 85509-19-9(Hazardous Substances Data)

Usage

Metabolic pathway

Flusilazole is stable to aqueous hydrolytic and photolytic degradation. Although flusilazole is relatively stable in soil and is detected in plant and animal samples, numerous degradation products have been reported. The primary metabolic pathway involves the cleavage of the methylenesilicon or/and methylene-triazole linkage. Another primary pathway involves aryl hydroxylation followed by conjugation. The primary metabolic/degradation pathways of flusilazole in soil, plant and animals are presented in Scheme 1.

Degradation

Aqueous hydrolysis and photolysis are not sigruficant degradation pathways for flusilazole (1). Flusilazole was stable (<5% decomposition) in sterile buffers at pH 5, 7 and 9 (25 °C) for 34 days (Cadwgan, 1983). No significant degradation was observed when fusilazole was irradiated with simulated sunlight for 30 days at 300-450 nm in sterile buffer solution at pH 7 (Carter, 1986).

InChI:InChI=1/C16H15F2N3Si/c17-14-5-1-12(2-6-14)16(13-3-7-15(18)8-4-13)22-11-21-10-19-9-20-21/h1-10,16H,11,22H2

Upstream product

• 41253-21-8 sodium triazole 
• 85491-26-5 (chloromethyl)bis(4-fluorophenyl)methylsilane 

Downstream Products

• 113576-68-4 2-{[bis-(4-fluorophenyl)-methyl-silanyl]-methyl}-2,4-dihydro[1,2,4]triazole-3-thione 

Relevant articles and documents

Flusilazole and synthesis method thereof

The invention discloses flusilazole and a synthesis method thereof. The synthesis method comprises the following steps: putting magnesium powder into a Grignard reaction kettle; adding an organic solvent and uniformly stirring; cooling and adding p-fluorobromobenzene in one step; mixing and stirring; dropwise adding the p-fluorobromobenzene, and keeping heat and reacting; cooling and storing to obtain a p-fluorobromobenzene Grignard reagent; raising the temperature of the p-fluorobromobenzene Grignard reagent; dropwise adding methyl chloromethyl dichlorosilane and carrying out heat insulation;recycling an organic solvent under negative pressure to obtain a flusilazole intermediate, magnesium bromide and magnesium chloride; adding DMF (Dimethyl Formamide), stirring, cooling and centrifuging; removing the magnesium bromide and the magnesium chloride to obtain a DMF mother solution; dissolving triazole sodium salt into formamide; adding the DMF mother solution and reacting; recycling theDMF under negative pressure and distilling in vacuum; cooling to obtain the flusilazole. The content of the flusilazole is greater than or equal to 95.0 percent and the yield is 80 to 90 percent; thesynthesis method has the advantages of moderate reaction conditions, safety in operation, low equipment requirements, low cost, no wastewater and easiness for operation and implementation, and is suitable for large-scale production of enterprises.

Integrated palladium-catalyzed arylation of heavier groupa 14 hydrides

A convenient procedure has been developed for the preparation of Groupa 14 compounds by integrated palladium-catalyzed cross-coupling of aromatic iodides with the corresponding Groupa 14 hydrides in the presence of a base. The reaction conditions can be applied to the cross-coupling of tertiary, secondary, and primary Groupa 14 compounds. In most cases, the desired arylated products were obtained in synthetically useful yields. Even in the case of aryl iodides containing OH, NH2, CN, or CO2R groups, the reactions proceeded with good to high yields with tolerance of these reactive functional groups. A possible application of this method is the unique synthesis of a fungicidal diarylmethyl(1H-1,2,4-triazol-1-ylmethyl)silane derivative. A convenient procedure has been developed for the preparation of Groupa 14 compounds by integrated palladium-catalyzed cross-coupling of aromatic iodides with the corresponding Groupa 14 hydrides in the presence of a base (see picture). Application of this method in the synthesis of a fungicidal diarylmethyl(1H-1,2,4-triazol-1-yl-methyl)silane derivative is demonstrated. Copyright

Synergistic Fungidical Active Substance Combinations

The present invention relates to novel active substance combinations which contain spiroxamine, which is known, a known azole and a known carboxamide and which are very suitable for controlling undesired phytopathogenic fungi.

Fungicide mixture

A composition comprising effective amounts ofa) a carbamate of the formula I where T is CH or N, n is 0, 1 or 2 and R is halogen, C1-C4-alkyl or C1-C4-haloalkyl, it being possible for the radicals R to be different if n is 2, andc) a compound III selected from the group consisting of the oxime ether carboxylate IIIa, the oxime ether carboxamide IIIb and the methoxyacrylate IIIc and optionally an oxime ether (II) and/or an azole (IV) as defined in the specification which exhibits a synergistically enhanced fungicidal effect is described.

Fungicide mixtures

A fungicidal mixture comprising a) an oxime ether of the formula I where the substituents have the following meanings: X is oxygen or amino (NH); Y is CH or N; Z is oxygen, sulfur, amino (NH) or C1-C4-alkylamino (N-alkyl); R′ is alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkylmethyl, or, if desired, substituted benzyl; a) an oxime ether of the formula I where the substituents have the following meanings: X is oxygen or amino (NH); Y is CH or N; Z is oxygen, sulfur, amino (NH) or C1-C4-alkylamino (N—C1-C4-alkyl); R′ is C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-alkenyl, C2-C6-haloalkenyl, C3-C6-alkynyl, C3-C6-haloalkynyl, C3-C6-cycloalkylmethyl, or is benzyl which can be partially or fully halogenated and/or can have attached to it one to three of the following radicals: cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and C1-C4-alkylthio; and at least one compound from groups b)-c): b.1) the oxime ether carboxylate of the formula IIa, b.2) the oxime ether carboxamide of the formula IIb, b.3) the methoxyacrylate of the formula IIc, c) one or more azole derivatives in a synergistically active amount.

Fungicidal mixtures

Fungicidal mixture, comprising a) an oxime ether carboxamide of the formula I STR1 where R is hydrogen or halogen and b) an azole derivative II selected from the group of the compounds II.1 to II.17 1-[(2RS,4RS;2RS,4SR)-4-bromo-2-(2,4-dichlorophenyl)-tetrahydrofuryl]-1H-1,2,4-triazole (II.1) 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol (II.2) (±)-4-chloro-4-[4-methyl-2-(1H-1,2,4-triazol-1-yl-methyl)-1,3-dioxolan-2-yl]phenyl 4-chlorophenyl ether (II.3) (E)-(R,S)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol (II.4) (Z)-2-(1H-1,2,4-triazol-1-ylmethyl)-2-(4-fluorophenyl)-3-(2-chlorophenyl)oxirane (II.5) 4-(4-chlorophenyl)-2-phenyl-2-(1H-1,2,4-triazolylmethyl)butyronitrile (II.6) 3-(2,4-dichlorophenyl)-6-fluoro-2-(1H-1,2,4-triazol-1-yl) quinazolin-4(3H)-one (II.7) bis(4-fluorophenyl)(methyl)(1H-1,2,4-triazol-1-yl-methyl)silane (II.8) (R,S)-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol (II.9) (1RS,5RS;1RS,5SR)-5-(4-chlorobenzyl)-2,2-dimenthyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol [sic] (II.10) N-propyl-N-[2-(2,4,6-trichlorophenoxy)ethyl]imidazole-1-carboxamide (II.11) (±)-1-[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole (II.12) (R,S)-1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol (II.13) (±)-2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazolyl)-propyl 1,1,2,2-tetrafluoroethyl ether (II.14) and (E)-1-[1-[[4-chloro-2-(trifluoromethyl)phenyl]imino]-2-propoxyethyl]-1H-imidazole (II.15) (RS)-2,4'-difluoro-α-(1H-1,2,4-triazol-1-ylmethyl)-benzhydryl alcohol (II.16) 2-p-chlorophenyl-2-(1H-1,2,4-triazol-1-ylmethyl)-hexanenitrile (II.17) in a synergistically active amount.

Fungicidal mixtures

A fungicidal mixture containing a) the oxime ether carboxamide of the formula I STR1 and b) an azole derivative II selected from the group of compounds II.1 to II.16 1-[(2RS,4RS;2RS,4SR)-4-bromo-2-(2,4-dichlorophenyl)tetra-hydrofuryl]-1H-1,2,4-triazole (II.1) 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol (II.2) (±)-4-chloro-4-[4-methyl-2-(1H-1,2,4-triazol-1-yl-methyl)-1,3-dioxolan-2-yl]phenyl 4-chlorophenyl ether (II.3) (E)-(R,S)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol (II.4) (Z)-2-(1H-1,2,4-triazol-1-ylmethyl)-2-(4-fluorophenyl)-3-(2-chlorophenyl)oxirane (II.5) 4-(4-chlorophenyl)-2-phenyl-2-(1H-1,2,4-triazolyl methyl)butyronitrile (II.6) 3-(2,4-dichlorophenyl)-6-fluoro-2-(1H-1,2,4-triazol-1-yl)quinazolin-4(3H)-one (II.7) bis(4-fluorophenyl)(methyl)(1H-1,2,4-triazol-1-yl-methyl)silane (II.8) (R,S)-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-l-yl)-hexan-2-ol (II.9) (1RS,5RS;1RS,5SR)-5-(4-chlorobenzyl)-2,2-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol (II.10) N-propyl-N-[2-(2,4,6-trichlorophenoxy)ethyl]-imidazole-1-carboxamide (II.11) (±)-1-[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole (II.12) (R,S)-1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol (II.13) (±)-2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl) propyl 1,1,2,2-tetrafluoroethyl ether (II.14) (E)-1-[1-[[4-chloro-2-(trifluoromethyl)phenyl]imino]-2-propoxyethyl]-1H-imidazole (II.15) and (RS)-2,4'-difluoro-α-(1H-1,2,4-triazol-1-yl-methyl)benzhydryl alcohol (II.16) in a synergistically active amount is described.

Synthesis of Fungicidal (1H-1,2,4-Triazol-1-yl-methyl)silanes and -siloxanes

The synthesis of FlusilazoleTM (1a) was substantially improved by thorough exclusion of oxygen nucleophiles in the reaction of (chloromethyl)bis(4-fluorophenyl)methylsilane with sodium 1H-1,2,4-triazolide.New α,α-diaryl-α-(1H-1,2,4-triazol-1-yl-methyl)siloxanes 3 were obtained firstly from diaryl(1H-1,2,4-triazol-1-yl-methyl)silanols or -silanolates, which were prepared by different methods from the corresponding silanol hydrochlorides and further treated with functional, linear oligodimethylsiloxanes or secondly from α,α-diaryl-α-(chloromethyl)siloxanes and 1-(trimethylsilyl)-1H-1,2,4-triazole.The siloxane 4 containing a triazolylmethyl group and additionally silicofunctional coupling groups could be synthesized by hydrosilylation of an α-triazolylmethyl-ω-vinylsiloxane with triethoxysilane. - Key Words: Fungicides / Silanes / Siloxanes / 1,2,4-Triazoles

Fungicidal 1,2,4-triazole derivatives

Silicon-containing 1,2,4-triazoles having broad-spectrum fungicidal activity have been discovered.