Discovery of Pyridalyl: A Novel Compound for Lepidopterous Pest Control

Sakamoto, Noriko; Saito, Shigeru; Hirose, Taro; Suzuki, Masaya; Matsuo, Sanshiro; Izumi, Keiichi; Nagatomi, Toshio; Ikegami, Hiroshi; Umeda, Kimitoshi; Tsushima, K.; Matsuo, Nobutake

doi:10.1021/bk-2005-0892.ch024

Cited by 7 publications

(9 citation statements)

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“…1), which is highly active against lepidopterous larvae. [1][2][3][4] In a previous study, we observed that Spodoptera litura larvae treated with lethal dosages of pyridalyl lost their vigor, mobile activity and body elasticity, dying within several hours of treatment. In contrast, the topical application of pyridalyl at sub-lethal dosages induced a unique symptom similar to a burn scar at the treated site.…”

Section: Introductionmentioning

confidence: 99%

Effects of Pyridalyl, a Novel Insecticidal Agent, on Cultured Sf9 Cells

2005

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Section: Introductionmentioning

confidence: 99%

Effects of Pyridalyl, a Novel Insecticidal Agent, on Cultured Sf9 Cells

2005

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“…Synthesis of flonicamid. 48) Pyridalyl was discovered and reported by Sumitomo Chemical Co., Ltd. 52,53) It has a 5-(trifluoromethyl) pyridine moiety as a key substructure in the molecule. According to the IRAC, the mode of action of pyridalyl is classified as unknown (UN).…”

Section: Insecticidementioning

confidence: 99%

“…Synthesis of pyridalyl. 52) Sulfoxaflor, 56,57) commercialized by Dow AgroSciences LLC in 2012, is an insecticide targeting sap-feeding pests. The sulfoxyimine functional group is rare and characteristic as a pesticide.…”

Section: Insecticidementioning

confidence: 99%

Synthesis and application of trifluoromethylpyridines as a key structural motif in active agrochemical and pharmaceutical ingredients

et al. 2021

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Herein, we provide a brief overview of the synthesis and applications of trifluoromethylpyridine (TFMP) and its derivatives in the agrochemical and pharmaceutical industries. Currently, the major use of TFMP derivatives is in the protection of crops from pests. Fluazifopbutyl was the first TFMP derivative introduced to the agrochemical market, and since then, more than 20 new TFMP-containing agrochemicals have acquired ISO common names. Several TFMP derivatives are also used in the pharmaceutical and veterinary industries; five pharmaceutical and two veterinary products containing the TFMP moiety have been granted market approval, and many candidates are currently undergoing clinical trials. The biological activities of TFMP derivatives are thought to be due to the combination of the unique physicochemical properties of the fluorine atom and the unique characteristics of the pyridine moiety. It is expected that many novel applications of TFMP will be discovered in the future.

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“…Starting from p-dihydroxybenzene (1), the Intermediates 3a-3c were prepared by the chlorination with sulfonyl chloride, which has been reported before (Scheme 1). 15,[25][26][27] Two routes were used to synthesize the aryloxyphenols 6b-6m and 7a-7k as shown in Scheme 2. Aryloxyphenols 6b-6f were prepared by Baeyer-Villiger oxidation/hydrolysis of aryloxybenzaldehydes 5b-5f with m-chloroperoxybenzoic acid (m-CPBA) in 50-85% yield.…”

Section: Chemistrymentioning

confidence: 99%