79983-71-4

Usage

Uses

Used in Agricultural Industry:
Hexaconazole is used as a systemic fungicide for the control of many fungi, particularly Ascomycetes and Basidiomycetes on a variety of crops. It is effective against powdery mildews, scabs, and rusts of vines, pome fruits, vegetables, and major diseases of small grain cereals.
Used in Rice Sheath Blight Control:
In China, India, and some other Asian countries, Hexaconazole is used as a fungicide for the control of rice sheath blight.
Used in Horticulture:
Hexaconazole is applicable to apples, grapes, bananas, vegetables, peanuts, and cereal crops as well as ornamental plants. It is especially suitable for the treatment of fungi diseases such as powdery mildew, rust, scab, brown blotch, and anthracnose caused by Ascomycetes and Basidiomycetes.
Used in Plant Stress Tolerance:
Exogenous application of Hexaconazole (15 mg/L) to Matricaria chamomilla (chamomile) plants improves water, proline, and protein contents, as well as increases non-enzymatic and enzymatic antioxidant and apigenin-7-glucoside content during a water deficit stress tolerance test.

References

https://en.wikipedia.org/wiki/Hexaconazole http://xb-agrochemical.com/3-5-hexaconazole.html/130471 http://krepl.in/wp-content/uploads/2014/10/KRIZOLE-5.pdf

Metabolic pathway

Metabolism of hexaconazole in plants involves primarily oxidation of the alkyl side chain.

Degradation

Hexaconazole is stable for at least 6 years at ambient temperature. It is stable to hydrolysis and photolysis in water.

InChI:InChI=1/C14H17Cl2N3O/c1-2-3-6-14(20,8-19-10-17-9-18-19)12-5-4-11(15)7-13(12)16/h4-5,7,9-10,20H,2-3,6,8H2,1H3

Synthetic route

n-butyl magnesium bromide (693-03-8) + 1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone (58905-16-1) → hexaconazole (79983-71-4)

Conditions	Yield
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone With magnesium bromide ethyl etherate In dichloromethane at 20℃; for 1.5h; Inert atmosphere; Stage #2: n-butyl magnesium bromide In diethyl ether; dichloromethane at 0 - 20℃; for 12h; Inert atmosphere;	12%

1-(2,4-dichlorophenyl)-2-(4-amino-4H-1,2,4-triazoliumyl)ethanone chloride (118227-30-8) → hexaconazole (79983-71-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrogenchloride; sodium nitrite / water / 1 h / 0 - 20 °C 2.1: magnesium bromide ethyl etherate / dichloromethane / 1.5 h / 20 °C / Inert atmosphere 2.2: 12 h / 0 - 20 °C / Inert atmosphere View Scheme

2,2',4'-trichloroacetophenone (4252-78-2) → hexaconazole (79983-71-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: isopropyl alcohol / 12 h / 80 °C 2.1: hydrogenchloride; sodium nitrite / water / 1 h / 0 - 20 °C 3.1: magnesium bromide ethyl etherate / dichloromethane / 1.5 h / 20 °C / Inert atmosphere 3.2: 12 h / 0 - 20 °C / Inert atmosphere View Scheme

copper(II) acetate monohydrate (6046-93-1) + hexaconazole (79983-71-4) → 2C14H17Cl2N3O*Cu(2+)*2C2H3O2(1-)

Conditions	Yield
In ethanol at 20℃; for 1h;	68%

zinc(II) nitrate hexahydrate + N,N-dimethyl-formamide (68-12-2, 33513-42-7) + hexaconazole (79983-71-4) → [ZnL34 (DMF)2](NO3)2

Conditions	Yield
In ethanol at 20℃; for 4h;	61%

hexaconazole (79983-71-4) → (+)-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol + (-)-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol

Conditions	Yield
In hexane; isopropyl alcohol at 20℃; Resolution of racemate; enantioselective reaction;
With chiralpak IC column In hexane; isopropyl alcohol at 20℃; Thermodynamic data; Solvent; Temperature; Resolution of racemate; enantioselective reaction;

1-(6-chloronicotinyl)-2-nitroiminoimidazoline (105827-78-9) + hexaconazole (79983-71-4) → C14H17Cl2N3O*C9H10ClN5O2

Conditions	Yield
at 100 - 110℃; Inert atmosphere;

1-(6-chloronicotinyl)-2-nitroiminoimidazoline (105827-78-9) + hexaconazole (79983-71-4) → 2C14H17Cl2N3O*C9H10ClN5O2

Conditions	Yield
at 100 - 110℃; Inert atmosphere;

1-(6-chloronicotinyl)-2-nitroiminoimidazoline (105827-78-9) + hexaconazole (79983-71-4) → 4C14H17Cl2N3O*C9H10ClN5O2

Conditions	Yield
at 100 - 110℃; Inert atmosphere;

1-(6-chloronicotinyl)-2-nitroiminoimidazoline (105827-78-9) + hexaconazole (79983-71-4) → 6C14H17Cl2N3O*C9H10ClN5O2

Conditions	Yield
at 100 - 110℃; Inert atmosphere;

1-(6-chloronicotinyl)-2-nitroiminoimidazoline (105827-78-9) + hexaconazole (79983-71-4) → 8C14H17Cl2N3O*C9H10ClN5O2

Conditions	Yield
at 100 - 110℃; Inert atmosphere;

hexaconazole (79983-71-4) → (R)-(+)-α-butyl-α-(2,4-dichlorophenyl)-1,2,4-triazole-1-ethanol (221627-81-2) + (S)-(-)-α-butyl-α-(2,4-dichlorophenyl)-1,2,4-triazole-1-ethanol (221627-82-3)

Conditions	Yield
With colistin sulfate-based polymer monolithic column In methanol; water at 20℃; Resolution of racemate; Green chemistry; enantioselective reaction;
In methanol; water at 20℃; Reagent/catalyst; Solvent; Resolution of racemate;

Upstream product

• 4252-78-2 2,2',4'-trichloroacetophenone 
• 693-03-8 n-butyl magnesium bromide 
• 58905-16-1 1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone 
• 118227-30-8 1-(2,4-dichlorophenyl)-2-(4-amino-4H-1,2,4-triazoliumyl)ethanone chloride 

Downstream Products

• 221627-81-2 (R)-(+)-α-butyl-α-(2,4-dichlorophenyl)-1,2,4-triazole-1-ethanol 
• 221627-82-3 (S)-(-)-α-butyl-α-(2,4-dichlorophenyl)-1,2,4-triazole-1-ethanol 

Relevant academic research and scientific papers

Antifungal Compounds

Compounds and compositions having antifungal activity, and methods of using the antifungal compounds and compositions, are described for use in treating fungal infections.

Novel alkylated azoles as potent antifungals

Fluconazole (FLC) is the drug of choice when it comes to treat fungal infections such as invasive candidiasis in humans. However, the widespread use of FLC has resulted in the development of resistance to this drug in various fungal strains and, simultaneously has occasioned the need for new antifungal agents. Herein, we report the synthesis of 27 new FLC derivatives along with their antifungal activity against a panel of 13 clinically relevant fungal strains. We also explore their toxicity against mammalian cells, their hemolytic activity, as well as their mechanism of action. Overall, many of our FLC derivatives exhibited broad-spectrum antifungal activity and all compounds displayed an MIC value of 0.03?μg/mL against at least one of the fungal strains tested. We also found them to be less hemolytic and less cytotoxic to mammalian cells than the FDA approved antifungal agent amphotericin B. Finally, we demonstrated with our best derivative that the mechanism of action of our compounds is the inhibition of the sterol 14α-demethylase enzyme involved in ergosterol biosynthesis.

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.

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.

Patch preparations for treating plants

The following invention introduces a patch preparation for treating plants, whereas the patch preparations comprise a chemical layer composed of at least one agrochemically active compound, at least one adhesive and optionally, one or more additives. The components are dispersed in a matrix state on a substrate which are then introduced on the roots of the plant to be treated.

Method for the treatment of plants with agrochemical tablet compositions

Novel method for applying agrochemicals to plants, which method consists in attaching to the surface of the plants tablets comprising at least one agrochemically active compound and at least one adjuvant, which is solid, liquid of pasty at room temperature, and optionally, one or more excipients optionally in admixture with one or more other additives and/or water.

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.

Fungicide compositions

Compositions of azole fungicides exhibiting reduced eye irritation are prepared by replacing a significant portion of the hydrocarbon solvent with a combination of propylene glycol and a long chain fatty alcohol.