| Identification | Back Directory | [Name]
oxathiapiprolin | [CAS]
1003318-67-9 | [Synonyms]
oxathiapiprolin
Oxathioapiprolin
Oxathiapiprolin@100 μg/mL in Methanol
Ethanone, 1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]- | [Molecular Formula]
C24H22F5N5O2S | [MDL Number]
MFCD30480157 | [MOL File]
1003318-67-9.mol | [Molecular Weight]
539.52 |
| Chemical Properties | Back Directory | [Description]
Oxathiapiprolin is now registered in numerous countries around the world, including Australia, Canada, China, Japan, and the United States, with the reviews confirming a highly favorable toxicological and environmental profile. | [Boiling point ]
613.9±65.0 °C(Predicted) | [density ]
1.54±0.1 g/cm3(Predicted) | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
0.78±0.10(Predicted) | [color ]
Off-White to Pale Yellow | [Henry's Law Constant]
2.8×102 mol/(m3Pa) at 25℃, Maniere et al. (2011) | [EPA Substance Registry System]
Ethanone, 1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]- (1003318-67-9) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS09 | [Signal word ]
Warning | [Hazard statements ]
H410 | [Precautionary statements ]
P273-P391-P501 | [Toxicity]
Acute toxicity studies No acute toxicity observed
Acute oral rat LD50 > 5000 mg kg−1
Acute dermal rat LD50 > 5000 mg kg−1
Acute inhalation rat LC50 > 5.1 mg kg−1
Rabbit eye or skin Not an irritant
Dermal sensitization in guinea pigs Nonsensitizing |
| Hazard Information | Back Directory | [Physical properties]
Melting point 146–148 °C (Form B)
Water solubility 0.175 mg l−1
log Kow 3.67
Kfoc 8368 g kg−1
Vapor pressure (20 °C) 1.14 × 10−6 Pa
Hydrolysis Stable
Aqueous photolysis DT50 ~ 15 d
Degradation in soil DT50 ~ 90 d | [Uses]
Zorvec is a novel oxathiapiprolin compound. Displays highly-active oomycete fungicide activity with a novel site of action. an oxysterol binding protein. | [Definition]
ChEBI: 1-(4-{4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone is an N-acylpiperidine that is N-acetyl 4-(1,3-thiazol-2-yl)piperidine in which the thiazole ring is substituted at position 4 by a 5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl group and in which one of the hydrogens of the acetyl group is replaced by a 5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl group. It is a N-acylpiperidine, a member of 1,3-thiazoles, a member of pyrazoles, an organofluorine compound, an isoxazoline and a tertiary carboxamide. | [Production Methods]
Oxathiapiprolin is produced commercially through a multi-step synthesis that assembles its complex piperidinyl-thiazole-isoxazole-pyrazole framework. The process begins with preparation of the 2,6-difluorophenyl isoxazole intermediate via cyclisation of a diketone with hydroxylamine. In parallel, a thiazole fragment is constructed and coupled to a piperidine derivative through selective substitution. The pyrazole unit, bearing a trifluoromethyl group, is then introduced via acylation to form the ethanone linkage. These fragments are joined under controlled conditions to yield the final N-acylpiperidine fungicide structure. Industrial production requires careful stereochemical control and purification (typically recrystallisation or chromatography) to achieve the technical-grade product. | [Mechanism of action]
Systemic, preventative with residual disease control. It acts via an oxysterol binding protein. Oxysterol-binding protein homologue inhibition (OSBPI). | [Pharmacology]
Oxathiapiprolin is the first member of a new class of highly active oomycete fungicides, the piperidinyl thiazole isoxazolines. It is effective at extremely low use rates and shows excellent preventative and curative efficacy, excellent antisporulant properties, and long residual control with protection of new growth. It was discovered using a high-throughput screening approach with diverse structural classes and optimized to this high potency chemotype by conformationally restricting the benzyl amide moiety using an isoxazoline ring as an amide bioisostere.
Oxathiapiprolin has a novel site of action, binding strongly to an OSBP with an, as yet, unknown cellular function. Oxathiapiprolin has the perfect combination of attributes to provide outstanding oomycete disease control and is being developed globally as DuPont? Zorvec? disease control. We expect that products containing oxathiapiprolin will become valuable tools for growers in their efforts to combat these diseases and sustainably and responsibly meet the growing global food production needs. | [Pesticide Type]
Fungicide |
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