Design, synthesis, crystal structure and insecticidal evaluation of novel arylpyrazole derivatives containing cyhalothroyl thiourea moiety

Han, Zhenyu; Wu, Wen‐Yuan; Chen, Fuli; Guan, Xi-Lin; Fu, Xiao-Huan; Jiang, Peng; Wan, Rong

doi:10.1080/10426507.2017.1292272

Cited by 8 publications

(5 citation statements)

References 24 publications

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“…Among the prominent methods, biomimetic synthesis simulates natural reactions within living organisms [80], while substructure splicing amalgamates active pesticide fragments to generate compounds with enhanced biological efficacy [81]. For the efficient synthesis of pyrethroids, the primary approach involves esterification, necessitating the initial production of chrysanthemic acid derivatives and alcohols (or aldehydes) [82][83][84][85].…”

Section: Synthesis Strategies Of Pyrethroids: Approaches and Mechanis...mentioning

confidence: 99%

“…Pyrethroids, renowned for their potent insecticidal properties and low mammalian toxicity, have evolved significantly, leveraging structural modifications to enhance stability and effectiveness [86]. The integration of aromatic groups into the alcoholic moiety has notably contributed to the improved stability of pyrethroids, allowing for their widespread application in crop protection [82][83][84][85]. This stability feature has propelled the exploration of various modifications, particularly in the alcohol and acid segments, underscoring the versatility of the synthesis approach [82][83][84][85].…”

Section: Synthesis Strategies Of Pyrethroids: Approaches and Mechanis...mentioning

confidence: 99%

“…The integration of aromatic groups into the alcoholic moiety has notably contributed to the improved stability of pyrethroids, allowing for their widespread application in crop protection [82][83][84][85]. This stability feature has propelled the exploration of various modifications, particularly in the alcohol and acid segments, underscoring the versatility of the synthesis approach [82][83][84][85].…”

Section: Synthesis Strategies Of Pyrethroids: Approaches and Mechanis...mentioning

confidence: 99%

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Pyrethrins and Pyrethroids: A Comprehensive Review of Natural Occurring Compounds and Their Synthetic Derivatives

Hodoșan,

Gîrd,

Ghica

et al. 2023

Plants

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This comprehensive scientific review provides an in-depth analysis of both the natural compounds, pyrethrins, and their synthetic derivatives, pyrethroids, focusing on their classification, biosynthesis, mechanism of action, general and pharmaceutical uses, as well as their toxicity and environmental impact. Pyrethrins, derived from certain plant species, have long been recognized for their potent insecticidal properties. The review begins by examining the classification of pyrethrins and pyrethroids, elucidating their structural characteristics and unique features within the field of natural and synthetic compounds. The biosynthetic pathways responsible for producing pyrethrins in plants are discussed, highlighting the enzymatic reactions and genetic regulation involved. In addition, the synthesis of pyrethroid derivatives is explored, including both natural and synthetic sources and potential optimization strategies. Understanding the mechanisms of action by which pyrethrins and pyrethroids exert their insecticidal effects is a crucial aspect of this review. Complex interactions with the nervous systems of target organisms are examined, providing insights into their selective toxicity and modes of action. In addition, the various applications of these compounds are explored, from their use in agriculture for pest control to their incorporation into household insecticides and potential pharmaceutical applications. The review also critically evaluates the potential toxicity of pyrethrins and pyrethroids to human health. By consolidating current knowledge and research findings, this review provides a comprehensive understanding of the properties and applications of pyrethrins and pyrethroids, highlighting their benefits and risks, and the importance of responsible and sustainable use in various areas.

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Section: Synthesis Strategies Of Pyrethroids: Approaches and Mechanis...mentioning

confidence: 99%

Section: Synthesis Strategies Of Pyrethroids: Approaches and Mechanis...mentioning

confidence: 99%

Section: Synthesis Strategies Of Pyrethroids: Approaches and Mechanis...mentioning

confidence: 99%

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Pyrethrins and Pyrethroids: A Comprehensive Review of Natural Occurring Compounds and Their Synthetic Derivatives

Hodoșan,

Gîrd,

Ghica

et al. 2023

Plants

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“…Thiourea derivatives can be synthesized with different methods [1,2] and uses in different applications such as the extraction of certain transition metals in acidic medium [3][4][5]. Multiple biological activities such as antibacterial [5,6] antifungal [6] antituberculosis [7] anticancer [8] antiviral [9] anticonvulsant [10] antioxidant [11] insecticidal [12] and herbicidal [13,14]. Benzoylthiourea derivatives are widely and successfully used in coordination chemistry.…”

Section: Introductionmentioning

confidence: 99%

Syntheses and X-ray Structure of N-(Benzothiazol-2-yl)-3-chlorobenzamide

Sow,

Odame,

Diouf

et al. 2024

Int. Res. J. Pure Appl. Chem.

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The reaction of 3-chloro-benzoyl chloride and 2-aminobenzothiazole in the presence of potassium thiocyanate yielded a yellowish solid C15H10ClN3OS2 (1). Reaction of 1 with cobalt chloride yield a yellowish solid C14H11ClN2O2S (2) which gives crystal suitable for X-ray analyses. The compounds were characterized by elemental analyses FTIR spectroscopy and melting point measurement. Compound 2 crystallizes in the triclinic space group Pī with the following parameters: a = 7.0299(2) Å b = 7.0466(2) Å c = 14.5490(2) Å a = 103.844(3)° β = 92.929(2)° g = 107.291(3) V = 662.33(4) Å3 Z= 2 R1 = 0.030 wR2 = 0.034. The asymmetric unit of (2) consists of one molecule in which the 3-chloro phenyl moiety and the benzothiazole-2-yl moiety form a dihedral angle of 6.417(4)°. An intramolecular O—H···O hydrogen bond occurs. In the crystal O—H···N and N—H···O hydrogen bonds link the molecules forming layers parallel to the ac plane.

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“…Thiourea derivatives have been reported in the literature for their multiple biological activities, including antibacterial [1][2][3][4], antifungal [5,6], antitubercular [7][8][9], anthelmintic [10], antiviral [11,12], anticancer [4,13,14], analgesic [15][16][17], anti-inflammatory [1,18], anti-diabetic [19,20], anticonvulsant [21], antithyroid [22,23], antioxidant [24], insecticidal [25], herbicidal [26], and rodenticidal [27] effects. Thiourea derivatives are also versatile intermediates for the synthesis of heterocyclic compounds such as 1,3-thiazoles, pyrimidines, 1,2,4-triazines and 1,3-quinazolines [28].…”

Section: Introductionmentioning

confidence: 99%

New N-acyl Thiourea Derivatives: Synthesis, Standardized Quantification Method and In Vitro Evaluation of Potential Biological Activities

Roman

Pintilie

Cãproiu³

et al. 2023

Antibiotics

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New N-acyl thiourea derivatives with heterocyclic rings have been synthesized by first obtaining isothiocyanate, which further reacted with a heterocyclic amine, characterized by (FT-IR, NMR spectroscopy and FT-ICR) and tested for their in vitro antimicrobial, anti-biofilm and antioxidant activities to obtain a drug candidate in a lead-optimization process. From the tested compounds, those bearing benzothiazole (1b) and 6-methylpyridine (1d) moieties revealed anti-biofilm activity against E. coli ATCC 25922 at MBIC values of 625 µg/mL. Compound 1d exhibited the highest antioxidant capacity (~43%) in the in vitro assay using 1,1-diphenyl-2-picrylhydrazyl (DPPH). Considering the in vitro results, the highest anti-biofilm and antioxidant activities were obtained for compound 1d. Therefore, a reversed-phase high-performance liquid chromatography (RP-HPLC) method has been optimized and validated for the quantitative determination of compound 1d. The detection and quantitation limits were 0.0174 μg/mL and 0.0521 μg/mL, respectively. The R2 correlation coefficient of the LOQ and linearity curves were greater than 0.99, over the concentration range of 0.05 μg/mL–40 μg/mL. The precision and accuracy of the analytical method were within 98–102%, confirming that the method is suitable for the quantitative determination of compound 1d in routine quality control analyses. Evaluating the results, the promising potential of the new N-acyl thiourea derivatives bearing 6-methylpyridine moiety will be further investigated for developing agents with anti-biofilm and antioxidant activities.

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Design, synthesis, crystal structure and insecticidal evaluation of novel arylpyrazole derivatives containing cyhalothroyl thiourea moiety

Cited by 8 publications

References 24 publications

Pyrethrins and Pyrethroids: A Comprehensive Review of Natural Occurring Compounds and Their Synthetic Derivatives

Pyrethrins and Pyrethroids: A Comprehensive Review of Natural Occurring Compounds and Their Synthetic Derivatives

Syntheses and X-ray Structure of N-(Benzothiazol-2-yl)-3-chlorobenzamide

New N-acyl Thiourea Derivatives: Synthesis, Standardized Quantification Method and In Vitro Evaluation of Potential Biological Activities

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