Fludioxonil

Fudioxonil is a synthetic phenylpyrrole-group substance. It is a kind of broad-spectrum, non-systemic fungicide, being used against Fusarium, Rhizoctonia, Alternaria and Botrytis cinerea. For dealing with the fungal diseases, it is usually applied in seed treatment as well as post-harvest treatment of fruits.
Fludioxonil Basic information
Description background Mechanism of action effect Indications Safety Preparation References
Product Name:Fludioxonil
Synonyms:Fludioxonil 0;Fludioxnil;4-(2,2-difluoro-1,3-benzdioxol-4-yl)-1h-pyrrole-3-carbonitrile;4-(2,2-difluoro-1,3-benzodioxol-4-yl)-1h-pyrrole-3-carbonitril;Scholar;4-(2,2-Difluorobenzo[d][1,3]dioxol-4-yl)-1H-pyrrole-3-carbonitrile;FREE SAMPLE NCV FLUDIOXONIL 25 G/L + MET ALXYL 37.5 G/L;Fludioxonil Solution, 1000ppm
CAS:131341-86-1
MF:C12H6F2N2O2
MW:248.18
EINECS:603-476-3
Product Categories:Agro-Products;Aromatics;PyrolesBuilding Blocks;Alpha sort;Heterocycles;Isotope Labelled Compounds;E-GAlphabetic;F;FA - FLPesticides;Fungicides;Heterocyclic Building Blocks;Pesticides&Metabolites;Thiazoles
Mol File:131341-86-1.mol
Fludioxonil Structure
Fludioxonil Chemical Properties
Melting point 199.4°
Boiling point 420.4±45.0 °C(Predicted)
density 1.55±0.1 g/cm3(Predicted)
vapor pressure 3.9 x 10-7 Pa (25 °C)
storage temp. Inert atmosphere,Room Temperature
solubility DMSO: Slightly Soluble,Methanol: Slightly Soluble
Water Solubility 1.8 mg l-1 in water at 25 °C
pka14.10±0.50(Predicted)
form neat
BRN 8393936
InChIKeyMUJOIMFVNIBMKC-UHFFFAOYSA-N
EPA Substance Registry SystemFludioxonil (131341-86-1)
Safety Information
Hazard Codes N
Risk Statements 50/53
Safety Statements 60-61
RIDADR 3077
WGK Germany 3
RTECS UX9347525
HazardClass 9
PackingGroup III
HS Code 29349990
Hazardous Substances Data131341-86-1(Hazardous Substances Data)
ToxicityLD50 in rats (mg/kg): >2000 orally; >2000 dermally; LC50 (4 hr) in rats: >2600 mg/m3 (Gehmann)
MSDS Information
Fludioxonil Usage And Synthesis
DescriptionFludioxonil is a synthetic phenylpyrrole-group substance. It is a kind of broad-spectrum, non-systemic fungicide, being used against Fusarium, Rhizoctonia, Alternaria and Botrytis cinerea. For dealing with the fungal diseases, it is usually applied in seed treatment as well as post-harvest treatment of fruits. Fludioxonil is effective in the treatment of many major seed diseases such as seedling blight, stem-base Browning, snow mould and common blunt. For post-harvest treatment, it can deal with Grey mould, storage rot, powdery mildew and black spot. It exerts its effect through interfering with the transport-associated phosphorylation of glucose as well as inhibiting glycerol synthesis, further inhibiting the mycelial growth. When used in combination with thiamethoxam and metalaxyl-M, fludioxonil can also be used for the treatment of pests such as peach-potato aphid, flea beetle and cabbage stem flea beetle.
Fludioxonil
backgroundFludioxonil is a non-systemic fungicide, introduced in 1993 by Ciba-Geigy (now Syngenta). It is used for the treatment of crops (particularly cereals, fruits and vegetables, and ornamental plants; often in combination with another fungicide such as cyprodinil). Brand names include seed treatments: Celest, Agri Star Fludioxonil 41 ST, Dyna-shield Fludioxonil, Maxim 4 FS, and Spirato 480 FS, as well as foliar applications: Switch (fludioxonil + cyprodinil) [1]. Fludioxonil is used against Fusarium, Rhizoctonia, Alternaria and Botrytis cinerea.
Mechanism of actionFludioxonil is a new type of pyrrole non-systemic, contact-killing broad-spectrum fungicide. As a seed treatment fungicide, the suspension seed coating agent can control many diseases. The application results show that fludioxonil root irrigation or soil treatment has very good effects on many root diseases such as wilt, root rot, fusarium wilt and vine blight of various crops. In addition, fludioxonil can also be used as a spray to prevent gray mold and sclerotia of various crops.
effect

Its mode of action is to inhibit transport-associated phosphorylation of glucose, which reduces mycelial growth rate.

IndicationsIt is used for the foliar treatment of wheat, barley, corn, peas, rape, rice, vegetables, grapes, lawns, and ornamental crops. It is used to control Fusarium nivalis, Tilletia rot, Rhizoctonia solani, etc. Special effects; treatment of grain and non-grain seeds, prevention and control of seed and soil-borne pathogens, such as Alternaria, Ascodia, Aspergillus, Fusarium, Bipolaris, Rhizoctonia and Penicillium bacteria.
SafetyFludioxonil is safe and harmless to crops at the recommended dose. The seed treatment of Silox is extremely safe for wheat stripe disease, netting disease, hard smut, and snow rot; corn is green and does not affect the emergence of seeds, and can promote the emergence of seeds in advance
PreparationTaking nitrophenol as raw material, the intermediate substituted aniline is prepared by etherification, fluorination and reduction, and then reacted with acrylonitrile by diazotization, and finally the ring is closed to obtain fludioxonil. The second preparation method takes substituted benzaldehyde as the starting material and undergoes condensation and cyclization to obtain fludioxonil. The reaction formula is as follows:
131341-86-1 synthesis
Referenceshttps://en.wikipedia.org/wiki/Fludioxonil
http://www.agchemaccess.com/Fludioxonil
UsesFludioxonil is a nonsystemic phenylpyrrole fungicide structurally related to pyrrolnitrin.
UsesAgricultural fungicide.
UsesFludioxonil is a non-systemic fungicide used for the seed treatment control of seedling blight, scab, brown root rot, ear blight, smut and leaf spots in cereals caused by Fusarium spp., Septuria nodurum, Tilletia caries, etc. It is also a contact fungicide controlling fruit rot, wood rot, stem rot and root rot in vines, fruits, field crops, vegetables and rice.
DefinitionChEBI: A member of the class of benzodioxoles that is 2,2-difluoro-1,3-benzodioxole substituted at position 4 by a 3-cyanopyrrol-4-yl group. A fungicide seed treatment for control of a range of diseases including Fusarium, Rhizoctonia an Alternaria .
Metabolic pathwayLimited data are available in the open literature. Information presented in this summary was abstracted from the data evaluation published by the Pesticide Safety Directorate (PSD, 1995). Fludioxonil is stable to hydrolytic and soil degradation. Oxidation and hydration of the cyano moiety was observed in and on soil surfaces and probably resulted from photolytic action to yield the corresponding amides and carboxylic acids. Extensive degradation occurred at the pyrrole ring in plants and animals, including hydroxylation and oxidation, followed by ring-opening. Modification of the benzodioxyl moiety was not observed.
DegradationFludioxonil(1) is stable to hydrolytic degradation (up to 30 days at 25 °C) over the pH range 5-9.
Fludioxonil degraded in pH 7 buffered solution when exposed to UV light generated by a xenon arc lamp with an estimated DT50 value of 10 days. The chemical nature of three major degradation products (each accounted ca. 15%) was not determined.
Fludioxonil Preparation Products And Raw materials
Raw materialsAcrylonitrile-->Nitrophenol
Prochloraz Sorbic acid Indoxacarb Triadimenol Thiodiazole copper IMINOCTADINE TRIS(ALBESILATE) Bromacil N-Methylpropionamide BARIUM THIOSULFATE Dinotefuran Teflubenzuron Fludioxonil-13C3 FLUDIOXONIL SOLUTION 100UG/ML IN ACETONITRILE 1ML FLUDIOXONIL PESTANAL, 100 MG Fludioxonil 3-CYANO-4-PHENYL-PYRROLE FLUDIOXONIL SOLUTION 100UG/ML IN TOLUENE 1ML 2,2-Difluoro-1,3-benzodioxole

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