ChemicalBook CAS DataBase List 131341-86-1

131341-86-1

Name	FLUDIOXONIL
CAS	131341-86-1
EINECS(EC#)	603-476-3
Molecular Formula	C12H6F2N2O2
MDL Number	MFCD01631158
Molecular Weight	248.19
MOL File	131341-86-1.mol

Synonyms

MAXIM Geoxe CELEST Savior Scholar cga173506 MaxiM PSP Beret Gold Fludioxnil FLUDIOXONIL Fludioxonil 0 Celest Saphire Fludioxonil [iso] FLUDIOXONIL STANDARD fludioxonil (bsi, pa e-iso) Fludioxonil 100mg [131341-86-1] 3-(2,2-Difluoro-benzodioxol-4-yl)-4-cyanopyrrole 4-（2，2-difluoro-1,3-benzodioxol-4-yl) pyrrole-3-carbonitrile 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 4-(2,2-difluoro-1,3-benzodioxol-4-yl)-1h-pyrrole-3-carbonitrile 1H-Pyrrole-3-carbonitrile, 4-(2,2-difluoro-1,3-benzodioxol-4-yl)- 4-(2,2-Difluorobenzo[d][1,3]dioxol-4-yl)-1H-pyrrole-3-carbonitrile

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.	0-6°C
solubility	DMSO: Slightly Soluble,Methanol: Slightly Soluble
form	neat
pka	14.10±0.50(Predicted)
Water Solubility	1.8 mg l^-1 in water at 25 °C
color	White to off-white
BRN	8393936
Henry's Law Constant	1.9×10⁴ mol/(m³Pa) at 25℃, Duchowicz et al. (2020)
Major Application	agriculture environmental
InChI	InChI=1S/C12H6F2N2O2/c13-12(14)17-10-3-1-2-8(11(10)18-12)9-6-16-5-7(9)4-15/h1-3,5-6,16H
InChIKey	MUJOIMFVNIBMKC-UHFFFAOYSA-N
SMILES	N1C=C(C2=C3C(=CC=C2)OC(F)(F)O3)C(C#N)=C1
EPA Substance Registry System	Fludioxonil (131341-86-1)

Safety Data

Symbol(GHS)	GHS09
Signal word	Warning
Hazard statements	H410
Precautionary statements	P273-P391-P501
Hazard Codes	N
Risk Statements	50/53 less more
Safety Statements	60-61 less more
RIDADR	3077
WGK Germany	3
RTECS	UX9347525
HazardClass	9
PackingGroup	III
HS Code	29349990
Storage Class	11 - Combustible Solids
Hazard Classifications	Aquatic Acute 1 Aquatic Chronic 1
Hazardous Substances Data	131341-86-1(Hazardous Substances Data)
Toxicity	LD50 in rats (mg/kg): >2000 orally; >2000 dermally; LC50 (4 hr) in rats: >2600 mg/m3 (Gehmann) less more

Raw materials And Preparation Products

Hazard Information

Usage

Fludioxonil is a nonsystemic phenylpyrrole fungicide structurally related to pyrrolnitrin.

Chemical Properties

The pure product is colorless crystals with an mp of 199.8°C, a relative density of 1.54 (20°C), a vapor pressure of 3.9×10-7 Pa (20°C), and a partition coefficient of 4.12 (25°C). Solubility at 25°C is: acetone 190 mg/L, methanol 44 mg/L, n-octanol 20 mg/L, toluene 2.7 mg/L, hexane 0.0078 mg/L, and water 1.8 mg/L. Hydrolysis does not occur at pH 5-9.

Uses

Agricultural fungicide.

Uses

Fludioxonil 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.

Uses

Fludioxonil is a nonsystemic phenylpyrrole fungicide structurally related to pyrrolnitrin.

Definition

ChEBI: 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 .

in vivo

Fludioxonil (40 mg/kg, i.g., once every three days for 80 days) inhibits tumor proliferation in mice^[2].

Animal Model:	MCF-7V-transplanted mice^[2]
Dosage:	40 mg/kg; every 3 days; 80 days
Administration:	i.g.
Result:	Accelerated tumor growth in vivo, and the expression of PCNA in animal tumor tissues also significantly increased.

Metabolic pathway

Limited 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.

Degradation

Fludioxonil(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.

Pesticide Type

Fungicide

Questions And Answer

Description
Fludioxonil 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.
;
background
Fludioxonil 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 action
Fludioxonil 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.
;
Indications
It 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.;
Safety
Fludioxonil 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;
Preparation
Taking 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:
;
References
https://en.wikipedia.org/wiki/Fludioxonil
http://www.agchemaccess.com/Fludioxonil ;

Spectrum Detail

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131341-86-1

Chemical Properties

Safety Data

Raw materials And Preparation Products

Raw materials

Hazard Information

Usage

Chemical Properties

Uses

Uses

Uses

Definition

in vivo

Metabolic pathway

Degradation

Pesticide Type

Questions And Answer

Description

background

Mechanism of action

effect

Indications

Safety

Preparation

References

Spectrum Detail

Supplier

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