Design, synthesis and insecticidal evaluation of aryloxy dihalopropene derivatives

Yang, Ji‐Chun; Li, Miao; Wu, Qiao; Liu, Changling; Chang, Xiu-Hui

doi:10.1016/j.bmc.2015.09.030

Cited by 16 publications

(8 citation statements)

References 18 publications

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“…7 The intermediate derivatization method (IDM) is a useful and highly efficient approach for agrochemical discovery. [8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24] Using this approach, novel molecules are constructed based on one or more chemical intermediates identified by retrosynthesis analysis. Applying such an analysis to saflufenacil, we found that saflufenacil can be produced starting from 2-chloro-4-fluorotoluene by oxidation, nitration, reduction and cyclization reactions, thus 2-chloro-4-fluorotoluene is a key raw material.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis and herbicidal evaluation of novel uracil derivatives containing an isoxazoline moiety

Yang

Guan

et al. 2020

Pest Management Science

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BACKGROUND Glyphosate is the most widely used and successful herbicide discovered to date, but its utility is now threatened by the occurrence of several glyphosate‐resistant weed species. Saflufenacil is a relatively new herbicide developed by BASF in 2010. It is a highly effective selective herbicide showing excellent control on broadleaf weeds (more than 90 species), significantly superior to other protoporphyrinogen oxidase (PPO) inhibitor herbicides at the level of weeds controlled. It is also effective against glyphosate‐resistant Conyza canadensis if used in combination with glyphosate. A series of novel uracil‐based PPO inhibitors containing an isoxazoline moiety were designed via the intermediate derivatization method, synthesized using a key saflufenacil raw material as starting material and evaluated for herbicidal activity. RESULTS The target compounds were characterized by 1H NMR and high‐resolution electrospray mass spectra. Bioassays indicated that some title compounds can control efficiently and effectively both broadleaf weeds and grassy weeds at low doses, especially the glyphosate‐resistant weeds C. canadensis and Eleusine indica. CONCLUSION This work provides a basis for further studies of 9b for control of a wider range of weeds, particularly for glyphosate‐resistant weeds.

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Section: Introductionmentioning

confidence: 99%

Design, synthesis and herbicidal evaluation of novel uracil derivatives containing an isoxazoline moiety

Yang

Guan

et al. 2020

Pest Management Science

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“…In this study, we sought to develop new pyrimidinamine derivatives with improved fungicidal activity by employing the intermediate derivatization method (IDM), a recently reported highly efficient approach to discover agrochemical candidates. − 2-Chloro-5-(chloromethyl)pyridine or 6-chloronicotinic acid derivatives were used as starting materials to obtain key intermediates, which produced a series of pyrimidinamine derivatives containing an aryloxy pyridine moiety (Figure ). The detailed synthesis, bioassay results, and structure–activity relationships of these compounds are discussed below.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Structure–Activity Relationship of New Pyrimidinamine Derivatives Containing an Aryloxy Pyridine Moiety

Guan

Liu

Chen

et al. 2017

J. Agric. Food Chem.

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The pyrimidinamine diflumetorim is an ideal template for the discovery of agrochemical lead compounds due to its unique mode of action, novel chemical structure, and lack of reported resistance. To develop a new pyrimidinamine fungicide effective against cucumber downy mildew (CDM), a series of new pyrimidinamine derivatives containing an aryloxy pyridine moiety were designed and synthesized by employing the recently reported intermediate derivatization method (IDM). The structures of all compounds were identified by H NMR, elemental analyses, HRMS, and X-ray diffraction. Bioassays demonstrated that some of the title compounds exhibited excellent fungicidal activities against CDM. Compound 9 gave the best activity (EC = 0.19 mg/L), which is significantly better than the commercial fungicides diflumetorim, flumorph, and cyazofamid. The relationship between structure and fungicidal activity of the synthesized pyrimidinamines was explored. The study showed that compound 9 is a promising fungicide candidate for further development.

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“…Very promisingly, the most active compound 178 (Figure 28) in this series displayed superior insecticidal activity than pyridalyl both in the greenhouse tests and field trials. 235 Around the same time, this research group disclosed a class of thienopyrimidine derivatives baring a DE moiety at the side chain (as shown in formula 179, Figure 28) as potential insecticides and acaricides. Some of these derivatives exhibited a 100% controlling effect against Myzus persicae and over 90% 29).…”

Section: ■ Introductionmentioning

confidence: 99%

Diaryl Ether: A Privileged Scaffold for Drug and Agrochemical Discovery

Chen

Xiong

Yang

et al. 2020

J. Agric. Food Chem.

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Diaryl ether (DE) is a functional scaffold existing widely both in natural products (NPs) and synthetic organic compounds. Statistically, DE is the second most popular and enduring scaffold within the numerous medicinal chemistry and agrochemical reports. Given its unique physicochemical properties and potential biological activities, DE nucleus is recognized as a fundamental element of medicinal and agrochemical agents aimed at different biological targets. Its drug-like derivatives have been extensively synthesized with interesting biological features including anticancer, anti-inflammatory, antiviral, antibacterial, antimalarial, herbicidal, fungicidal, insecticidal, and so on. In this review, we highlight the medicinal and agrochemical versatility of the DE motif according to the published information in the past decade and comprehensively give a summary of the target recognition, structure–activity relationship (SAR), and mechanism of action of its analogues. It is expected that this profile may provide valuable guidance for the discovery of new active ingredients both in drug and pesticide research.

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Design, synthesis and insecticidal evaluation of aryloxy dihalopropene derivatives

Cited by 16 publications

References 18 publications

Design, synthesis and herbicidal evaluation of novel uracil derivatives containing an isoxazoline moiety

Design, synthesis and herbicidal evaluation of novel uracil derivatives containing an isoxazoline moiety

Design, Synthesis, and Structure–Activity Relationship of New Pyrimidinamine Derivatives Containing an Aryloxy Pyridine Moiety

Diaryl Ether: A Privileged Scaffold for Drug and Agrochemical Discovery

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