131341-86-1 Usage
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
Uses
Different sources of media describe the Uses of 131341-86-1 differently. You can refer to the following data:
1. Fludioxonil is a nonsystemic phenylpyrrole fungicide structurally related to pyrrolnitrin.
2. Agricultural fungicide.
3. 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.
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 .
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.
Check Digit Verification of cas no
The CAS Registry Mumber 131341-86-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,1,3,4 and 1 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 131341-86:
(8*1)+(7*3)+(6*1)+(5*3)+(4*4)+(3*1)+(2*8)+(1*6)=91
91 % 10 = 1
So 131341-86-1 is a valid CAS Registry Number.
InChI:InChI=1/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
131341-86-1Relevant articles and documents
Synthesis of Pyrroles via Consecutive 6π-Electrocyclization/Ring-Contraction of Sulfilimines
Feichtinger, Niklas J.,Haut, Franz-Lucas,Müller, Mira,Magauer, Thomas,Plangger, Immanuel,Podewitz, Maren,Streit, Tim-Niclas,Wein, Lukas A.,Wurst, Klaus
, p. 9002 - 9008 (2021/07/01)
We present a modular, synthetic entry to polysubstituted pyrroles employing readily available 2,5-dihydrothiophenes. Ring-opening of the heterocycle provides access to a panel of 1,3-dienes which undergo pyrrole formation in the presence of inexpensive chloramine-T trihydrate. The transformation is conducted in an open flask and proceeds at ambient temperatures (23 °C) in nondry solvents. A careful adjustment of the electronics and sterics of the 1,3-diene precursor allows for the isolation of key intermediates. DFT studies identified a reaction mechanism that features a 6π-electrocyclization of a sulfilimine intermediate followed by spontaneous ring-contraction to reveal the pyrrole skeleton.
A method for preparing Fludioxonil
-
, (2018/04/02)
The invention relates to the field of organic synthesis and discloses a method for preparing Fludioxonil. Fludioxonil has a structure represented by a formula (VIII) shown in the description. The method is characterized by comprising the step of enabling a 2-cyano-3-(2,2-difluoro-1,3-benzodioxy-4-yl)acrylic acid compound represented by a formula (I) shown in the description to be in contact reaction with p-methylbenzenesulfonyl methyl isocyanide represented by a formula (VII) shown in the description in a solvent in the presence of alkali, wherein the rate of change of the pH value of a reaction solution during reaction is lower than 1 per minute, the pH value is controlled in the range of 10-14.0, R1 is NHR2 or OR3, R2 is H or C1-C6 alkyl, and R3 is C1-C6 alkyl. The yield of the Fludioxonil product prepared by the method disclosed by the invention can reach over 95%, the purity of the product can reach over 98wt%, and the content of difficultly-removed impurities, i.e., M305 and M319 in the product can be lower than 0.1 wt%; and the prepared Fludioxonil product is white, so that the step and cost for dealing with color problems are avoided.
Process for the preparation of substituted difluorobenzo-1,3-dioxoles
-
, (2008/06/13)
The reaction of 2,2-difluorobenzo-1,3-dioxole with (a) an alkali metal or an alkali metal compound and then (b) a compound R1 -Z1 l in which Z1 is a leaving group, or with an aldehyde produces compounds of formula I STR1 wherein R1 l is --OH, --SH, --CHO, --CN, --COOH, --B(OH)2, --COX, with X being Cl or Br, or is --COOR2, --SiR32 or --B(OR2)2, with R2 being a C1 -C12 alcohol moiety without the hydroxy group, wherein R1 is further --Cn H2n COOR2, with n being an integer from 1 to 4, or linear or branched C1 -C12 hydroxyalkyl which is unsubstituted or is substituted by --F, --CN, C1 -C6 alkoxy, phenyl, fluorophenyl, C1 -C4 alkoxy-phenyl, C1 -C4 alkylthio-phenyl, C1 -C4 alkyl-phenyl, C1 -C4 fluoroalkyl-phenyl, nitrophenyl or by cyanophenyl, or wherein R1 is a benzyl alcohol which is unsubstituted or is substituted by F, C1 -C4 alkoxy, C1 -C4 alkylthio, C1 -C4 alkyl, C1 -C4 fluoroalkyl, nitro or by cyano, or is C1 -C12 acyl, or wherein R 1 is a radical of formula II STR2 wherein R5 is --CN, --CF3, --COOR2, --CO--NHR2 or --CONR22, R3 and R4 are a direct bond or each is H, or R3 is H and R4 independently has the meanings of R5, or R3 and R4 together are --CH2 --NR6 --CH2 --, --CH2 --NR6 --CO-- or --CO--NR6 --CO-- wherein R6 is the radical of a removable protecting group, or wherein further R1 is a radical of formula III STR3 Insecticides or fungicides can be prepared from the compounds of formula I. 3-(2,2-difluorobenzodioxol-4-yl)-4-cyanopyrrole can be prepared by reacting 4-metallo-2,2-difluorobenzodioxole (III) with an unsaturated nitrile and then with a sulfonylmethyl isocyanide in a one-pot process. The compounds III are novel intermediates.
