Chapter 4 Fluorine-Containing Agrochemicals: An Overview of Recent Developments

Theodoridis, George

doi:10.1016/s1872-0358(06)02004-5

Cited by 144 publications

(138 citation statements)

References 75 publications

Supporting

Mentioning

138

Contrasting

Order By: Relevance

“…The incorporation of fluorine atoms in organic molecules (e.g., materials, 1 agrochemicals, 2–3 pharmaceuticals 4 ) is becoming increasingly common, as a result of the unique electronic and steric properties of fluorine atoms. 5–12 Consequently, 19 F NMR is applied ever more frequently in structural assignments.…”

Section: Introductionmentioning

confidence: 99%

Prediction of ¹⁹F NMR Chemical Shifts for Fluorinated Aromatic Compounds

et al. 2018

View full text Add to dashboard Cite

Scaling factors are reported for use in predicting 19F NMR chemical shifts for fluorinated (hetero)aromatic compounds with relatively low levels of theory. Our recommended scaling factors were developed using a curated data set of >50 compounds, with 100 individual 19F shifts spanning a range of >150 ppm. With a maximum deviation of 6.5 ppm between experimental and computed shifts, or 4% of the range tested, these scaling factors allow for the assignment of chemical shifts to specific fluorines in multifluorinated aromatics. The utility of this approach is highlighted by several structural reassignments.

show abstract

Section: Introductionmentioning

confidence: 99%

Prediction of ¹⁹F NMR Chemical Shifts for Fluorinated Aromatic Compounds

et al. 2018

View full text Add to dashboard Cite

show abstract

“…The importance of fluorine in the life science industry has been reviewed; [1][2][3] in addition, the discovery of crop protection products containing the pyridine ring has been surveyed recently. 4 Furthermore, the synthesis of selected trifluoromethyl pyridines contained within biologically active molecules has been reported.…”

Section: Introductionmentioning

confidence: 99%

The importance of trifluoromethyl pyridines in crop protection

Burriss

Edmunds

Emery

et al. 2018

Pest Management Science

View full text Add to dashboard Cite

The pyridine ring, substituted by a trifluoromethyl substituent has been successfully incorporated into molecules with useful biological properties. During the period 1990 to September 2017, 14 crop protection products bearing a trifluoromethyl pyridine have been commercialized or proposed for an ISO common name, covering fungicides, herbicides, insecticides and nematicides. Chemical processes have been developed to provide trifluoromethyl pyridine intermediates, from non-fluorinated pyridine starting materials, at scale and with affordable costs of goods. These attractive starting materials were readily adopted by research chemists, and elaborated through simple chemical modifications into new active ingredients. In a second approach, substituted trifluoromethyl pyridine rings have been constructed from acyclic, trifluoromethyl starting materials, which again has served to identify new active ingredients. Molecular matched pair analysis reveals subtle, yet important differences in physicochemical and agronomic properties of trifluoromethyl pyridines compared with the phenyl analogues. This review focuses on the past 27 years, seeking to identify reasons behind the success of such research programmes, and inspire the search for new crop protection chemicals containing the trifluoromethyl pyridine ring. © 2017 Society of Chemical Industry.

show abstract

“…It is known that fluorinecontaining chemicals can be useful for controlling agricultural pests (Maienfisch and Hall, 2004). The inclusion of single fluorine atoms and trifluoromethyl groups into small molecules can significantly increase their biological activity by promoting electrostatic interactions with biological targets, increasing their metabolic stability, as well as improving cellular membrane permeability and corresponding bioavailability (Muller et al, 2007;Purser et al, 2008;Nagib and MacMillan, 2011;Hagmann, 2008;Yamazaki et al, 2009;Theodoridis, 2006;Yale, 1959). Many amides show mosquito repellent activity, such as N,Ndiethyl-meta-toluamide (DEET, today's gold standard), carboxamides (Katritzky et al, 2010), acylpiperidines (Katritzky et al, 2008), etc., as well as insecticidal activity (Dong et al, 2012;Park et al, 2002;Hwang and Mulla, 1980;Blade, 1990).…”

Section: Introductionmentioning

confidence: 99%

Insecticidal and repellent properties of novel trifluoromethylphenyl amides II

Tsikolia

Bernier

Agramonte

et al. 2018

Pesticide Biochemistry and Physiology

View full text Add to dashboard Cite

A B S T R A C TThis project focused on the design, synthesis, and testing of trifluoromethylphenyl amides (TFMPAs) as potential mosquitocides and repellents. Fourteen compounds were evaluated for toxicity against larvae and adults of Aedes aegypti. Several compounds were toxic against Aedes aegypti (larval, adult and feeding bioassays) and Drosophila melanogaster (glass-surface contact assay), but were much less toxic than fipronil, with toxicity ratios ranging from 100-fold in the larval assay to 100,000-fold for topical application to adult insects. In repellency bioassays to determine minimum effective dosage (MED), compound N-(2,6-dichloro-4-(trifluoromethyl)phenyl)-2,2,3,3,3-pentafluoropropanamide (7b) repelled Ae. aegypti females at lower concentration, 0.017 ( ± 0.006) μmol/cm 2 , than N, N-diethyl-meta-toluamide (DEET) 0.026 ( ± 0.005) μmol/cm 2 . 2-Chloro-N-(3-(trifluoromethyl)phenyl)acetamide (6a) performed better than DEET against two species of mosquitoes: it repelled Ae. aegypti females at 0.013 ( ± 0.006) μmol/cm 2 and Anopheles gambiae females (in a warm body repellent assay), at a standard exposure of 2 nmol/cm 2 . These studies revealed novel active structures that could further lead to compounds with better repellent activity.

show abstract

Chapter 4 Fluorine-Containing Agrochemicals: An Overview of Recent Developments

Cited by 144 publications

References 75 publications

Prediction of ¹⁹F NMR Chemical Shifts for Fluorinated Aromatic Compounds

Prediction of ¹⁹F NMR Chemical Shifts for Fluorinated Aromatic Compounds

The importance of trifluoromethyl pyridines in crop protection

Insecticidal and repellent properties of novel trifluoromethylphenyl amides II

Contact Info

Product

Resources

About

Chapter 4 Fluorine-Containing Agrochemicals: An Overview of Recent Developments

Cited by 144 publications

References 75 publications

Prediction of 19F NMR Chemical Shifts for Fluorinated Aromatic Compounds

Prediction of 19F NMR Chemical Shifts for Fluorinated Aromatic Compounds

The importance of trifluoromethyl pyridines in crop protection

Insecticidal and repellent properties of novel trifluoromethylphenyl amides II

Contact Info

Product

Resources

About

Prediction of ¹⁹F NMR Chemical Shifts for Fluorinated Aromatic Compounds

Prediction of ¹⁹F NMR Chemical Shifts for Fluorinated Aromatic Compounds