trans-Caryophyllene (TC) is a sesquiterpene commonly found as volatile component in many different aromatic plants. Although the phytotoxic effects of trans-caryophyllene on seedling growth are relatively explored, not many information is available regarding the phytotoxicity of this sesquiterpenes on weed germination and on adult plants. The phytotoxic potential of TC was assayed in vitro on weed germination and seedling growth to validate its phytotoxic potential on weed species. Moreover, it was assayed on the metabolism of Arabidopsis thaliana adult plants, through two different application ways, spraying and watering, in order to establish the primary affected organ and to deal with the unknown mobility of the compound. The results clearly indicated that TC inhibited both seed germination and root growth, as demonstrated by comparison of the ED50 values. Moreover, although trans-caryophyllene-sprayed adult Arabidopsis plants did not show any effect, trans-caryophyllene-watered plants became strongly affected. The results suggested that root uptake was a key step for the effectiveness of this natural compound and its phytotoxicity on adult plants was mainly due to the alteration of plant water status accompanied by oxidative damage.

Chalcone (1,3-diphenyl-2-propen-1-one) is an aromatic ketone precursor of important molecules in plants such as flavonoids or anthocyanins. Its phytotoxicity has been demonstrated on different plant species, but to date little is known about the mechanisms of action of this secondary metabolite at plant cellular level. Detailed analysis by light and transmission electron microscopy (TEM) was conducted to examine the root meristems' ultrastructure of control and chalcone-treated Arabidopsis seedlings. Mitochondrial dysfunction was analysed by measuring mitochondrial membrane potential with JC-1 fluorochrome. Finally, acridine orange/ethidium bromide staining was used for the detection of programmed cell death. Microscopy revealed tissue alterations, inhibition of root hair formation and important changes after 7 and 14 d at the chalcone IC50 value. Chalcone-treated cells showed signs of programmed cell death such as mitochondrial condensation, disruption of organelles and chromatin fragmentation. Acridine orange/ethidium bromide staining confirmed the programmed cell death, which could be induced by the reduction of mitochondrial transmembrane potential (DYm) that was detected after chalcone treatment. These results confirm the phytotoxic activity of chalcone on Arabidopsis seedlings, the alteration of mitochondrial membrane potential and the induction of programmed cell death.

Citral is a monoterpene commonly found as volatile component in many different aromatic plants. Although many studies have identified the presence of citral in phytotoxic essential oils, this work determines for the first time the potential herbicidal effect of citral on weeds. The use of citral against weeds and crops resulted in the potential for the management of barnyardgrass, redroot pigweed, and ribwort. Clear morphological differences were observed between adult thale cress plants exposed to citral in two different application methods: spraying and watering. Citral-sprayed and citral-watered thale cress plants showed completely different effects after treatment, suggesting that foliar or root absorption can determine the effectiveness of this compound. This work demonstrates that citral is effective not only on seedling metabolism but also on adult plants by inhibiting growth and development altering the plant oxidative status.

-This review provides information on the biological activities of chalcones (whether natural or synthetic derivatives) on different organisms, as well as an overview of the functions and possible new applications of these plant secondary metabolites on crop protection, as eco-friendly pesticides and weed control agents. Naturally occurring chalcones have been used in traditional medicine for many years; however, recent scientific advances have shown that these molecules have a broad range of biological activities in a variety of organisms. A review on the major sources of chalcones and the main molecular events involved in the modes of action of these natural products is achieved. Chalcones are molecules with a broad spectrum of biological activities, which are of great interest in agriculture to control weeds and unwanted pests.Keywords: mode of action, secondary metabolites, crop protection, pesticide, fungicide, antiviral, phytotoxicity. RESUMO -Esta avaliação fornece informações sobre as atividades biológicas de chalconas (quer derivados naturais ou sintéticos) em diferentes organismos, bem como uma visão geral das funções e eventuais novas aplicações desses metabólitos secundários de plantas em proteção de cultivos e pesticidas orgânicos e para controlar as plantas daninhas. Durante muitos anos têm sido utilizadas na medicina tradicional chalconas de ocorrência natural; no entanto, os recentes avanços científicos têm mostrado que essas moléculas têm vasta gama de atividades biológicas em uma variedade de organismos. Este estudo permite ter uma ideia das principais fontes de chalconas e dos eventos moleculares envolvidos nos principais mecanismos de ação desses produtos naturais. As chalconas são moléculas com um largo espectro de atividade biológica, de grande interesse na agricultura para controlar plantas daninhas e pragas indesejadas.Palavras-chave: modo de ação, metabólitos secundários, proteção de cultivos, pesticida, fungicida, antiviral, fitotoxicidade.

Mode of action of farnesene, a volatile sesquiterpene commonly found in the essential oils of several plants, was deeply studied on the model species Arabidopsis thaliana. The effects of farnesene on the Arabidopsis root morphology were evaluated by different microscopic techniques. As well, microtubules immunolabeling, phytohormone measurements and ROS staining helped us to elucidate the single or multi-modes of action of this sesquiterpene on plant metabolism. Farnesene-treated roots showed a strong growth inhibition and marked modifications on morphology, important tissue alterations, cellular damages and anisotropic growth. Left-handed growth of farnesene-treated roots, reverted by taxol (a known microtubule stabilizer), was related to microtubule condensation and disorganization. As well, the inhibition of primary root growth, lateral root number, lateral root length, and both root hairs length and density could be explained by the strong increment in ethylene production and auxin content detected in farnesene-treated seedlings. Microtubule alteration and hormonal unbalance appear as important components in the mode of action of farnesene and confirm the strong phytotoxic potential of this sesquiterpene.