Turning renewable resources into value-added products: Development of rosin-based insecticide candidates

Gao, Yanqing; Li, Jian; Song, Zhanqian; Song, Jié; Shang, Shibin; Xiao, Gengsheng; Wang, Zongde; Rao, Xiaoping

doi:10.1016/j.indcrop.2015.07.067

Cited by 18 publications

(19 citation statements)

References 29 publications

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“…It is noteworthy that neat rosin can be acrylated as well [125]. As an important material in rosin chemistry, acrylpimaric acid can be used for preparation of diallyl acrylpimarate [123], polyesters of acrylated rosin and polyethylene glycols [125], epoxy resins [126,127], acrylpimaryl dichloride [128,129], acrylpimaric acid amides [130], cyclic diamide [131], quaternary ammonium salts [132,133,134,135,136], calcium and zinc salts [137] as well as polyesters [138]. Moreover, it can be used directly as an epoxy curing agent [139].…”

Section: Rosin-based Chemicalsmentioning

confidence: 99%

“…Thiadiazole group-containing amides of dehydroabietic or acrylpimaric acids can be prepared from adequate rosin acid, thiosemicarbazide and an acyl chloride according to Scheme 40, and using such separation methods as filtration, vacuum drying, recrystallization and column chromatography [130]. They can be potentially applied as insecticides [130,190].…”

Section: Rosin-based Chemicalsmentioning

confidence: 99%

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Advances in Rosin-Based Chemicals: The Latest Recipes, Applications and Future Trends

et al. 2019

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A comprehensive review of the publications about rosin-based chemicals has been compiled. Rosin, or colophony, is a natural, abundant, cheap and non-toxic raw material which can be easily modified to obtain numerous useful products, which makes it an excellent subject of innovative research, attracting growing interest in recent years. The last extensive review in this research area was published in 2008, so the current article contains the most promising, repeatable achievements in synthesis of rosin-derived chemicals, published in scientific literature from 2008 to 2018. The first part of the review includes low/medium molecule weight compounds: Especially intermediates, resins, monomers, curing agents, surfactants, medications and biocides. The second part is about macromolecules: mainly elastomers, polymers for biomedical applications, coatings, adhesives, surfactants, sorbents, organosilicons and polysaccharides. In conclusion, a critical evaluation of the publications in terms of data completeness has been carried out with an indication of the most promising directions of rosin-based chemicals development.

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Section: Rosin-based Chemicalsmentioning

confidence: 99%

Section: Rosin-based Chemicalsmentioning

confidence: 99%

Advances in Rosin-Based Chemicals: The Latest Recipes, Applications and Future Trends

et al. 2019

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“…Due to its availability and attractive properties, rosin has been widely used for centuries. Plant-derived compounds present in rosin exhibit high biological activity, making it a potential component for herbicidal or insecticidal formulations. , …”

Section: Introductionmentioning

confidence: 99%

“…Plant-derived compounds present in rosin exhibit high biological activity, making it a potential component for herbicidal or insecticidal formulations. 4,5 Abietic acid (AA) is the main constituent of rosin (IUPAC name abieta-7,13-dien-18-oic acid, (1R,4aR,4bR,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,4b,5,6,10,10a-decahydrophenanthrene-1-carboxylic acid or silvic acid), which is present in the largest quantities in pines. AA is a yellowish solid, insoluble in water, with a melting point at 172−175 °C.…”

Section: ■ Introductionmentioning

confidence: 99%

Biobased Ionic Liquids with Abietate Anion

Klejdysz

Łęgosz

Czuryszkiewicz

et al. 2016

ACS Sustainable Chem. Eng.

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The present study is focused on the utilization of naturally occurring abietic acid in the synthesis of high added-value compounds with attractive characteristics. The synthesis of ILs derived from abietic acid was conducted using ion-exchange or neutralization methods, and the products were obtained with high yields exceeding 85%. The study confirmed strong influence of the chemical structure on the physicochemical properties of the obtained compounds, such as solubility, thermal stability, and phase transitions. The results also revealed excellent deterrent properties of ILs with abietate anions toward S. granarius, T. conf usum, and T. granarium, reaching or exceeding the values calculated for azadirachtin. The best results were achieved for cations containing long alkyl substituentstetraalkylammonium and 1-alkyl-3-methylimidazolium cations. Additionally, the obtained compounds exhibited antioxidant properties in the DPPH radical scavenging assay. The highest activity was observed for tetraalkylammonium cations. The obtained results allow for a conclusion that abietate ionic liquids with both antifeedant and antioxidant activity can be successfully implemented into storage crop protection.

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“…It is virtually and economically impossible to develop and screen candidates with fungicidal activity from among numberless compounds. The development of new quantitative structure-activity relationship (QSAR) methods, with simple molecular indexes, is a promising shortcut to resolve the cost and time issues [22]. The QSAR method enables the calculation of numerous quantitative descriptors on the basis of molecular structural information and is very useful to optimize important aspects such as fungicidal activity or toxicity.…”

Section: Introductionmentioning

confidence: 99%

New α-Methylene-γ-Butyrolactone Derivatives as Potential Fungicidal Agents: Design, Synthesis and Antifungal Activities

Wu¹,

Wang²,

Gao³

et al. 2016

Molecules

Self Cite

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Abstract:In consideration of the fact that the α-methylene-γ-butyrolactone moiety is a major bio-functional group in the structure of carabrone and possesses some agricultural biological activity, forty-six new ester and six new ether derivatives containing α-methylene-γ-butyrolactone moieties were synthesized, and their fungicidal activities against Colletotrichum lagenarium and Botrytis cinerea were investigated. Most of the synthesized compounds showed moderate to significant fungicidal activity. Among them, halogen atom-containing derivatives showed better activity than others, especially compounds 6a,d which exhibited excellent fungicidal activity against C. lagenarium, with IC 50 values of 7.68 and 8.17 µM. The structure-activity relationship (SAR) analysis indicated that ester derivatives with electron-withdrawing groups on the benzene ring showed better fungicidal activity than those with electron-donating groups. A quantitative structure-activity relationship (QSAR) model (R 2 = 0.9824, F = 203.01, S 2 = 0.0083) was obtained through the heuristic method. The built model revealed a strong correlation of fungicidal activity against C. lagenarium with the molecular structures of these compounds. These results are expected to prove helpful in the design and exploration of low toxicity and high efficiency α-methylene-γ-butyrolactone-based fungicides.

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Turning renewable resources into value-added products: Development of rosin-based insecticide candidates

Cited by 18 publications

References 29 publications

Advances in Rosin-Based Chemicals: The Latest Recipes, Applications and Future Trends

Advances in Rosin-Based Chemicals: The Latest Recipes, Applications and Future Trends

Biobased Ionic Liquids with Abietate Anion

New α-Methylene-γ-Butyrolactone Derivatives as Potential Fungicidal Agents: Design, Synthesis and Antifungal Activities

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