To cope with the rising food demand, modern agriculture practices are based on the indiscriminate use of agrochemicals. Although this strategy leads to a temporary solution, it also severely damages the environment, representing a risk to human health. A sustainable alternative to agrochemicals is the use of plant metabolites and plant-based pesticides, known to have minimal environmental impact compared to synthetic pesticides. Retama raetam is a shrub growing in Algeria’s desert areas, where it is commonly used in traditional medicine because of its antiseptic and antipyretic properties. Furthermore, its allelopathic features can be exploited to effectively control phytopathogens in the agricultural field. In this study, six compounds belonging to isoflavones and flavones subgroups have been isolated from the R. raetam dichloromethane extract and identified using spectroscopic and optical methods as alpinumisoflavone, hydroxyalpinumisoflavone, laburnetin, licoflavone C, retamasin B, and ephedroidin. Their antifungal activity was evaluated against the fungal phytopathogen Stemphylium vesicarium using a growth inhibition bioassay on PDA plates. Interestingly, the flavonoid laburnetin, the most active metabolite, displayed an inhibitory activity comparable to that exerted by the synthetic fungicide pentachloronitrobenzene, in a ten-fold lower concentration. The allelopathic activity of R. raetam metabolites against parasitic weeds was also investigated using two independent parasitic weed bioassays to discover potential activities on either suicidal stimulation or radicle growth inhibition of broomrapes. In this latter bioassay, ephedroidin strongly inhibited the growth of Orobanche cumana radicles and, therefore, can be proposed as a natural herbicide.

The study of allelopathic activity of plants and the isolation and characterization of the responsible allelochemicals can lead to the development of environment friendly alternative approaches to weed control. Conyza species are invasive weeds that use allelopathic activity as part of a successful strategy to outcompete neighboring plants. Broomrape weeds are parasitic plants that use host-induced germination and the formation of a haustorium as strategies to infect host plants. The control of broomrape infection in most affected crops is limited or non-existing. In the current study, we investigated the allelopathic activity of Conyza bonariensis organic extracts in suicidal germination and radicle growth of four broomrape species (Orobanche crenata, Orobanche cumana, Orobanche minor and Phelipanche ramosa). A bioactivity-driven fractionation of Conyza bonariensis extracts led to the identification of two germination-inducing molecules and two growth-inhibitory compounds. The germination-inducing metabolites had species-specific activity being hispidulin active on seeds of O. cumana and methyl 4-hydroxybenzoate active in P. ramosa. The growth-inhibitory metabolites (4Z)-lachnophyllum lactone and (4Z,8Z)-matricaria lactone strongly inhibited the radicle growth of all parasitic weed species studied. Some structure–activity relationships were found as result of the study herein presented.

Cuscuta species are obligate parasitic plants that infect the stems of a wide range of hosts including many crop and weed species causing severe agricultural problems. Using in vitro experiments to screen organic extracts prepared from fifteen autotrophic weed species found in agricultural fields infested with Cuscuta campestris, we have identified for the first time a strong phytotoxic activity in Conyza bonariensis extract against C. campestris. Additional pot experiments revealed that seven day-old Cuscuta seedlings had reduced capacity to coil and properly attach on Conyza plants, leading to reduced parasitic weed infection. Via activity-guided fractionation of Conyza extracts, we isolated and identified the acetylenic furanone (4Z)-lachnophyllum lactone as the major active component, with a concentration required to achieve reduction of 50% Cuscuta seedling growth (IC₅₀) of 24.8 µg/mL. The discovery of (4Z)-lachnophyllum lactone bioactivity could aid the development of efficient and sustainable management strategies for C. campestris, whose control is limited or non-existent.

Cuscuta campestris is a parasitic weed species with noxious effects in broadleaf crops worldwide. The control of Cuscuta in the majority of crops affected is limited or non-existing. We tested, for the first time, the effect of eighteen metabolites in in vitro-grown Cuscuta seedlings. We found that 2-benzoxazolinone, hydrocinnamic acid and pisatin caused the strongest inhibition of seedling growth. In addition to seedling growth, pisatin caused necrosis of the Cuscuta seedling, occurring mostly at the seedling shoot. Scopoletin and sesamol treatments caused toxicity, observed as a black staining, only at the Cuscuta root apices, while caffeic acid, ferulic acid and vanillic acid caused toxicity, observed as brown staining, in the root apices. The structure–activity relationships in four structural derivatives of 2-benzoxazolinone, and five structural derivatives of hydrocinnamic acid, were also studied. The identification of new herbicidal modes of action against Cuscuta is the first step in creating new alternatives to sustainable chemical control of parasitic weeds.

Cuscuta campestris is a parasitic weed species that inflicts worldwide noxious effects in many broadleaf crops due to its capacity to withdraw nutrients and water directly from the crop vascular system using haustorial connections. Cuscuta campestris control in the majority of crops affected is non-existent, and thus, research for the development of control methods is needed. Hydrocinnamic acid occurs naturally in the rhizosphere, playing regulatory roles in plant–plant and plant–microbe communities. The toxicity of hydrocinnamic acid against C. campestris was recently identified. In the present work, a structure–activity relationship study of 21 hydrocinnamic acid analogues was performed to identify key structural features needed for its allelopathic action against the seedling growth of this parasitic plant. The findings of this study provide the first step for the design of herbicides with enhanced activity for the control of C. campestris infection.

Cuscuta campestris Yunck. is a parasitic weed responsible for severe yield losses in crops worldwide. The selective control of this weed is scarce due to the difficult application of methods that kill the parasite without negatively affecting the infected crop. trans-Cinnamic acid is secreted by plant roots naturally into the rhizosphere, playing allelopathic roles in plant–plant communities, although its activity in C. campestris has never been investigated. In the search for natural molecules with phytotoxic activity against parasitic weeds, this work hypothesized that trans-cinnamic acid could be active in inhibiting C. campestris growth and that a study of a series of analogs could reveal key structural features for its growth inhibition activity. In the present structure–activity relationship (SAR) study, we determined in vitro the inhibitory activity of trans-cinnamic acid and 24 analogs. The results showed that trans-cinnamic acid’s growth inhibition of C. campestris seedlings is enhanced in eight of its derivatives, namely hydrocinnamic acid, 3-phenylpropionaldehyde, trans-cinnamaldehyde, trans-4-(trifluoromethyl)cinnamic acid, trans-3-chlorocinnamic acid, trans-4-chlorocinnamic acid, trans-4-bromocinnamic acid, and methyl trans-cinnamate. Among the derivatives studied, the methyl ester derivative of trans-cinnamic acid was the most active compound. The findings of this SAR study provide knowledge for the design of herbicidal treatments with enhanced activity against parasitic weeds.