ChemInform Abstract: Trifluoromethylpyridines as Building Blocks for New Agrochemicals. Discovery of a New Turf Herbicide

Haga, Takahiro; Tsujii, Yasuhiro; Hayashi, Kiyotada; Kimura, Fumio; Sakashita, N.; Fujikawa, K.

doi:10.1002/chin.199129313

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(3 citation statements)

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“…In the case of the herbicide fluazifop‐ P ‐butyl, results indicated that an improved translocation, and thus bioavailability of this molecule is observed when compared with the molecular matched pair phenyl analogue (Fig. ) …”

Section: Physicochemical Considerationsmentioning

confidence: 99%

“…10). 12 The impact of introducing a nitrogen atom into an aromatic ring in medicinal chemistry has recently been reviewed. 31 Listing many varied examples, striking differences in properties such as in vitro activity, bioavailability, functional activity or safety profiles have been observed using this approach.…”

Section: Physicochemical Considerationsmentioning

confidence: 99%

“…The electron‐withdrawing effect of the trifluoromethyl group in combination with the pyridine nitrogen activates the chlorine adjacent to the nitrogen in intermediates 1 , 2 , and 3 towards substitution by nucleophiles, allowing further chemical transformations to be performed easily. The application of such intermediates, together with discovery of the herbicides fluazifop‐ P ‐butyl and fluazasulfuron, the fungicide fluazinam and the insecticide chlorfluazuron have been summarized in Haga et al and are shown in Fig. .…”

Section: Products Originating From Chlorine–fluorine Exchange Technolmentioning

confidence: 99%

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The importance of trifluoromethyl pyridines in crop protection

Burriss

Edmunds

Emery

et al. 2018

Pest Management Science

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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.

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Section: Physicochemical Considerationsmentioning

confidence: 99%

Section: Physicochemical Considerationsmentioning

confidence: 99%

Section: Products Originating From Chlorine–fluorine Exchange Technolmentioning

confidence: 99%

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