Fluensulfone I Nematicides

Fluensulfone [5-chloro-2-(3,4,4-trifluorobut-3-enylsulfonyl)-1,3-thiazole] is a new nematicide for chemical control of Plant Parasitic Nematodes (PPNs). Chemically, Fluensulfone is a member of the fluoroalkenyl thioether group and it is designed in manner that it posses excellent nematicidal activity but lacks many of the drawbacks of other chemical controls, as exemplified by its relatively low toxicity to non-target organisms.

Fluensulfone is effective against a number of PPNs including species of Meloidogyne which are responsible for a significant proportion of nematode crop yield loss. Also, Fluensulfone has been shown to significantly reduce root infection and penetration by Meloidogyne javanica, Meloidogyne incognita and Meloidogyne arenaria.

Fluensulfone: 2D and 3D Structure

Fluensulfone was launched in 2014 by ADAMA which claims it to be “true nematicide“ as it causes irreversible nematicidal activity resulting in pest mortality within 24 to 48 hours rather than temporary nematostatic (repelling or immobilizing) activity as seen with organophosphates and carbamates.

Mechanism for Activity

There is no mechanism available right now.

In a study using model genetic organism Caenorhabditis elegans proved that C. elegans is susceptible to the irreversible nematicidal effects of Fluensulfone. Researchers found that:

a. Fluensulfone has pleiotropic actions.

b. It inhibits development, egg-laying, egg-hatching, feeding and locomotion. In the case of feeding and locomotion, an early excitation precedes the gross inhibition.

The profile of these effects is notably distinct from other classes of anthelmintic and nematicide: the inhibition of motility caused by Fluensulfone is not accompanied by the hypercontraction which is characteristic of organophosphates and carbamates. Also, C. elegans mutants that are resistant to the carbamate Aldicarb and the macrocyclic lactone Ivermectin retain susceptibility to Fluensulfone.

Whilst the dose required is higher than that which has nematicidal activity against Meloidogyne spp. the profile of effects on motility, egg-hatching and survival is similar to that reported for plant parasitic nematodes. These data indicate Fluensulfone’s mode of action is distinct from currently available nematicides and it therefore presents a promising new chemical entity for crop protection [1].

Developer

It is developed and launched by ADAMA in 2014.

Reported Activities for Fluensulfone

% Mortality (C. elegans life cycle [L1] @ 1 mM) = 100 ± 0

% Mortality (C. elegans life cycle [Adult] @ 1 mM) = 97.0 ± 12

Summary

Common name: Dipymetitrone; MCW-2

Trademarks: NIMITZ

Molecular Formula: C7H5ClF3NO2S2

CAS Registry Number: 318290-98-1

CAS Name: 5-chloro-2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)thiazole

Molecular Weight: 291.70

SMILES: F/C(CCS(C1=NC=C(Cl)S1)(=O)=O)=C(F)/F

InChI Key: XSNMWAPKHUGZGQ-UHFFFAOYSA-N

InChI: InChI=1S/C7H5ClF3NO2S2/c8-5-3-12-7(15-5)16(13,14)2-1-4(9)6(10)11/h3H,1-2H2

Mechanism of Action: Unknown

Activity: Nematicide

Status: Launched 2014 (US)

Chemical Class: Thiazoles; Sulfonyls; Flourine Containing; Tri-Flouro Molecules; Sulphur containing; Thio containing; Small-molecules

Originator: ADAMA

Fluensulfone Synthesis

WO2001002378A1: The patent reports synthesis for Fluensulfone and its various derivatives. The synthesis starts with the alklylation of the 2-mercaptothiazole by 4-bromo-1,1,2-trifluorobutene. The thiazole obtained is subsequently chlorinated by N-chlorosuccinimide, and the sulfide function oxidized to the sulphone by hydrogen peroxide in the presence of acetic acid.

 Identifications:

1H NMR (Estimate) for Fluensulfone

Adverse Reports:

Nothing available.

Others:

The readers are welcome to share their views.

References:

1. Kearn, J.; et. al. Fluensulfone is a nematicide with a mode of action distinct from anticholinesterases and macrocyclic lactones. Pestic Biochem Physiol 2014, 109, 44-57. (free article)

2. Watanabe, Y.; et. al. Nematicidal trifluorobutenes. WO2001002378A1

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