Amino acid chemistry in crop protection

Lamberth, Clemens

doi:10.1016/j.tet.2010.06.008

Cited by 57 publications

(43 citation statements)

References 168 publications

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“…This five‐membered heterocycle adds to α‐chlorooacrylonitrile in a thermal cycloaddition reaction to the trisubstituted pyrrole 71 . Introduction of two further substituents by bromination and N‐alkylation leads to chlorfenapyr ( 73 ) (Scheme ) .…”

Section: Oxazole and Isoxazole Derivatives As Intermediates In The Symentioning

confidence: 99%

“…An appropriate process for the synthesis of etoxazole starts with the acylation of the phenylglycine ester 74 with 2,6‐difluorobenzoyl chloride and the subsequent reduction of the ester function of the intermediate amidoester 75 . The resulting aminoalcohol 76 is then converted into the oxazoline derivative etoxazole ( 22 ) by chlorination and base‐catalyzed cyclization (Scheme ) .…”

Section: Synthesis Of Oxazole‐based and Isoxazole‐based Agrochemicalsmentioning

confidence: 99%

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Oxazole and Isoxazole Chemistry in Crop Protection

Lamberth

2018

Journal of Heterocyclic Chem

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An overview is given of the significance of the oxazole and isoxazole scaffolds in crop protection chemistry. The main herbicidally, fungicidally, and insecticidally active oxazole and isoxazole classes are presented, together with their synthesis routes, modes of action, and biological efficacies. In addition, the role of oxazoles and isoxazoles as lead structure or as intermediate in the synthesis of other agrochemicals is reported. Also, partially and fully saturated oxazole and isoxazole derivatives such as oxazolines, isoxazolines, oxazolidines, and isoxazolidines, oxygenated derivatives such as oxazolones and isoxazolones as well as annulated derivatives, such as benzoxazoles and benzisoxazoles, are covered.

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Section: Oxazole and Isoxazole Derivatives As Intermediates In The Symentioning

confidence: 99%

Section: Synthesis Of Oxazole‐based and Isoxazole‐based Agrochemicalsmentioning

confidence: 99%

Oxazole and Isoxazole Chemistry in Crop Protection

Lamberth

2018

Journal of Heterocyclic Chem

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“…Amino acids as bifunctional building blocks are suitable starting materials for the construction of heterocyclic scaffolds of agrochemicals . This is demonstrated by the conversion of α‐methylvalinamide ( 56 ) into the imidazolinone ring of imazethapyr ( 58 ), an acetohydroxyacid synthase (AHAS/ALS) inhibiting herbicide, which selectively controls a wide variety of broadleaf weeds and grasses in soybeans and other crops at low use rates (Scheme ).…”

Section: Different Possibilities For the Synthesis Of Heterocyclic Agmentioning

confidence: 99%

Heterocyclic chemistry in crop protection

2013

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An overview is given of the significance of heterocycles in crop protection chemistry, which is enormous as more than two-thirds of all agrochemicals launched to the market within the last 20 years belong to this huge group of chemicals. This review focuses on two important aspects of heterocyclic agrochemistry: the different roles of heterocyclic scaffolds in crop protection agents and the major possibilities for their synthesis.

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“…On the other hand, the increasing concern about adverse effects of pesticides on health and environment, evidenced by the introduction of new pesticide registration procedures (see, for example, the Food Quality Protection Act in the United States [5]), prompted the investigation of new pesticides, including natural product-based pesticides [6], to replace the compounds that could no longer be used, due to the new registration requirements. Examples can be found in a number of reviews [7,8]. In the attempt to obtain more efficient compounds, ferrocenyl group was introduced as a substituent in compounds known to be active.…”

Section: Ferrocene-containing Agrochemicalsmentioning

confidence: 99%