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Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
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Acetals are formed by reacting two equivalents of alcohol with carbonyl compounds like aldehydes or ketones. Acetals are unaffected by bases, nucleophiles, oxidizing agents, and reducing agents. They serve as protecting groups for aldehydes and ketones. Acetals can be easily formed and also easily removed via mild acid hydrolysis.
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All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for...
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Rational Design of β-Ketonitrile Acaricides through Binding-Mode-Guided Isosteric Ring Replacement.

Cong Zhou1, Jingwen Ge1, Zhong Li1

  • 1Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China.

Journal of Agricultural and Food Chemistry
|December 26, 2025
PubMed
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New β-ketonitrile acaricides show potent activity against spider mites by inhibiting succinate dehydrogenase (SDH). Compound A23 offers improved efficacy and reduced fish toxicity, presenting a promising candidate for pest management.

Keywords:
computational modelingisosteric ring replacementmode of actionstructure activity relationshipβ-ketonitrile acaricide

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Area of Science:

  • Agricultural Chemistry
  • Entomology
  • Toxicology

Background:

  • β-Ketonitrile acaricides are crucial for controlling phytophagous mites by targeting succinate dehydrogenase (SDH).
  • Developing novel derivatives is essential for effective mite management and overcoming resistance.
  • SDH inhibitors (SDHIs) are a significant class of agrochemicals with broad applications.

Purpose of the Study:

  • To rationally design novel β-ketonitrile acaricides using a binding mode similarity-based isosteric ring replacement strategy.
  • To identify potent acaricidal compounds with an improved safety profile.
  • To investigate the mechanism of action of the designed compounds.

Main Methods:

  • Applied a structure-based drug design approach incorporating isosteric ring replacement.
  • Synthesized arylcarbonitrile and arylacrylonitrile derivatives containing SDHI fungicidal moieties.
  • Evaluated acaricidal activity against various developmental stages of *Tetranychus cinnabarinus* and assessed acute fish toxicity.

Main Results:

  • The optimal compound, A23 (3-trifluoromethyl-1*H*-methylpyrazole moiety), demonstrated high efficacy against adult, nymph, and egg stages of *Tetranychus cinnabarinus*.
  • Compound A23 exhibited significantly lower acute fish toxicity (3.2-fold decrease) compared to cyenopyrafen.
  • Mechanism studies confirmed SDH inhibition via conserved cation-π interactions and H-bonds.

Conclusions:

  • The designed β-ketonitrile acaricides, particularly A23, show excellent acaricidal activity and a favorable ecological safety profile.
  • These findings provide a potential candidate for developing new acaricides and offer insights for designing other SDHI agrochemicals.
  • The study highlights the success of a rational design strategy for novel pesticide development.