Structure-related antifeedant activity of halolactones with a <i>p</i>
-menthane system against the lesser mealworm, <i>Alphitobius diaperinus</i>
 Panzer

Szczepanik, M.; Grudniewska, Aleksandra; Zawitowska, Beata; Wawrzeńczyk, Czesław

doi:10.1002/ps.3634

Cited by 15 publications

(19 citation statements)

References 33 publications

(49 reference statements)

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“…Up to the present day, many biologically active lactones, mostly with isoprenoid skeleton, have been synthesized by our research team. They exhibited antifeedant activity towards storage insect pests, [16][17][18][19][20] aphids, 21,22 lesser mealworm 23,24 or colorado potato beetle. 2,25 Some of the obtained lactones also inhibited the growth of pathogenic fungi.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of β-aryl-γ-lactones and relationship: Structure – antifeedant and antifungal activity

et al. 2015

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Eighteen racemic β-aryl-γ -lactones derived from simple aromatic aldehydes have been obtained in the chemical synthesis. Iodolactones (5c and 6c) were synthesized from (E)-4-(benzo [d][1 ,3 ]-dioxol-5 -yl)-but-3-en-2-one (1). Reductive dehalogenation of iodolactones 5a-c and 6a-c afforded γ -ethyl-γ -lactones (7a-c, 8a-c) whereas the unsaturated lactones (9a-c, 10a-c) were obtained by dehydrohalogenation of iodolactones. All synthesized lactones were fully characterized by spectroscopic data (NMR, IR, HRMS) and subjected to the tests on the antifeedant activity towards Tribolium confusum, Trogoderma granarium and Sitophilus granaries as well to the tests on the antifungal activity towards four Fusarium species. The biological tests allowed to find some relationships between the structure and biological activity of the compounds studied. γ -Ethyl-γ -lactones 7a-c, 8a-c and unsaturated lactones 9a-c, 10a-c were usually stronger antifeedants than their parent iodolactones 5a-c and 6a-c. trans-Iodolactones 6a-c were more active than cis isomers 5a-c both in antifeedant and antifungal assays. The structure of aromatic substituent was the key factor in antifungal activity. The lactones with benzo [d][1,3]dioxole ring (5c, 6c, 7c, 8c, 9c) were the most active whereas those with unsubstituted benzene ring exhibited almost no activity.

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Section: Introductionmentioning

confidence: 99%

Synthesis of β-aryl-γ-lactones and relationship: Structure – antifeedant and antifungal activity

et al. 2015

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“…Aguerin B and chlorojanerin, isolated from Rhaponticum pulchrum , have been shown to be good feeding deterents against three stored‐product insect pests: Sitophilus granarius , Trogoderma granarium and Tribolium confusum . The synthetic lactones are also potent antifeedants . The chlorolactone obtained from β ‐cyclocitral is a good antifeedant against Tribolium confusum .…”

Section: Introductionmentioning

confidence: 99%

“…The chlorolactone obtained from β ‐cyclocitral is a good antifeedant against Tribolium confusum . Lactones with a p ‐menthane system have exhibited activity against stored‐product pests, aphids, lesser mealworm and Colorado potato beetle . Additionally, this group of compounds is known for a wide spectrum of antibacterial activity .…”

Section: Introductionmentioning

confidence: 99%

Lactones 46. Synthesis, antifeedant and antibacterial activity ofγ-lactones with ap-methoxyphenyl substituent

et al. 2015

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The results of biological tests showed that halogen atom removal significantly increased the antifeedant properties of γ-lactones with a p-methoxyphenyl substituent. Unsaturated lactones are most promising in the context of their possible industrial application as crop protection agents. Further structural modifications of lactones with aromatic rings are needed to find important structural factors increasing the antibacterial activity.

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“…Estudos anteriores têm demonstrado que a introdução de um grupamento lactona em estruturas de compostos tais como (±)-limoneno, (R)-(-)-mirtenol, (-)-α-pineno, (+)-3-careno, (±)-canfeno aumenta consideravelmente a ação "antifeedants" em insetos [26,27,28]. As plantas das famílias Asteraceae e Apiaceae são particularmente ricas em lactonas [29].…”

Section: "Antifeedants" De Origem Naturalunclassified

“…No entanto, isto nãoé regra e sendo assim, os testes biológicos devem incluir a avaliação da atividade de todos os estereoisômeros possíveis dos compostos bioativos quirais [29].…”

Section: Fatores Químicosunclassified

An Overview of the Insects Antifeedants

Pires¹,

Carvalho²

2017

Revista Ciencias Exatas E Naturais

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Resumo: A preocupação com o meio ambiente e o modo como as atividades econômicas nele se organizam, tem sido tema de vários estudos. Muitos insetos atuam, disseminando cultivos importantes para a sobrevivência do homem. Uma saída mais coerenteé fazer uso de práticas de manejo integrado de pragas, que tem como propósito, manter a densidade populacional de um organismo abaixo do nível de dano econômico, sem a necessidade da utilização de pesticidas químicos (agroquímicos). Neste sentido, se encaixa um termo conhecido por muitos pesquisadores daárea de ecologia química, que são os Antifeedants-Substâncias capazes de inibir a alimentação do inseto, por mecanismos fisiologicamente complexos. O objetivo dos pesquisadores acerca deste tema envolve a possibilidade de extrair das plantas um bioinseticida que, portanto, não cause danos ambientais e/ou sociais, como ocorre ao se fazer o uso indiscriminado dos pesticidas sintéticos. A síntese química, entretanto, pode contribuir muito, na formulação de um bioinseticida, utilizando como protótipo a molécula isolada de determinada planta. Neste estudo pretende-se fazer uma revisão da literatura em torno da ação antialimentar ("antifeedants") que determinados compostos, naturais ou sintéticos, podem exercer em insetos, aqui encarados como pragas agrícolas.Palavras-chave: bioinseticidas; controle de pragas; inibição alimentar. Abstract:The concern about the environment and the way in which economic activities are organized in it has been the subject of many studies. Many insects have the task of disseminating cultivations that are important for human survival. A more coherent way out is to make the use of practices of integrated pest management, which has the purpose of keeping the population density of an organism below the level of economic damage, without the need of chemical pesticides (agrochemicals) utilization. In this sense, appears a well-known term among researchers in the field of chemical ecology: the "Antifeedants" -Substances capable of inhibiting the feeding of the insect by physiologically complex mechanisms. The objective of researchers on this theme involves the possibility of extracting from plants a bioinsecticide that, therefore, does not cause environmental and/or social damages, which happens when the indiscriminate use of synthetic pesticide is made. The chemical synthesis, however, can contribute greatly to the formulation of a bioinsecticide, using as a prototype the isolated molecule from a certain plant. This study intends to review the literature on the antifeedants action that certain compounds, natural or synthetic ones, may exert on insects, here displayed as agricultural pests.

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Structure-related antifeedant activity of halolactones with a p -menthane system against the lesser mealworm, Alphitobius diaperinus Panzer

Cited by 15 publications

References 33 publications

Synthesis of β-aryl-γ-lactones and relationship: Structure – antifeedant and antifungal activity

Synthesis of β-aryl-γ-lactones and relationship: Structure – antifeedant and antifungal activity

Lactones 46. Synthesis, antifeedant and antibacterial activity ofγ-lactones with ap-methoxyphenyl substituent

An Overview of the Insects Antifeedants

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