Transformation of the Herbicide Sulcotrione into a Root Growth Enhancer Compound by Sequential Photolysis and Hydrolysis.

Xanthene-1,9-dione-3,4-dihydro-6-methylsulfonyl (1), the main product of sulcotrione phototransformation on plant leaves, was slowly hydrolyzed into 2-hydroxy-4-methylsulfonylbenzoic acid (2) and 1,3-cyclohexanedione (3) in aqueous solution. Interestingly, the rate of hydrolysis was significantly enhanced in the presence of roots of monocotyledonous plants, while the same treatment showed adverse effects on broadleaf weeds. Root growth enhancement varied according to the plant species and concentrations of compound 2, as shown with Zea mays roots. Compound 2 is a derivative of salicylic acid that is known to be a plant signaling messenger. Compound 2 was, therefore, able to mimic some known effects of this phytohormone. This work showed that a pesticide like sulcotrione was transformed into a compound exhibiting a positive impact on plant growth. This study exemplified a rarely reported situation where chemical and biological chain reactions transformed a xenobiotic into a compound exhibiting potential beneficial effects.

Synergistic health effects between chemical pollutants and electromagnetic fields.

Humans and ecosystems are exposed to highly variable and unknown cocktail of chemicals and radiations. Although individual chemicals are typically present at low concentrations, they can interact with each other resulting in additive or potentially synergistic mixture effects. This was also observed with products obtained by radiation actions such as sunlight or electromagnetic fields that can change the effects of chemicals, such as pesticides, and metal trace elements on health. Concomitant presence of various pesticides and their transformation products adds further complexity to chemical risk assessment since chronic inflammation is a key step for cancer promotion. Degradation of a parent molecule can produce several by-products which can trigger various toxic effects with different impacts on health and environment. For instance, the cocktail of sunlight irradiated sulcotrione pesticide has a greater cytotoxicity and genotoxicity than parent molecule, sulcotrione, and questions about the impact of photochemical process on environment. Adjuvants were shown to modify the biological features of pesticides. Addition of other elements, metals or biological products, can differently enhance cell toxicity of pesticides or electromagnetic radiations suggesting a synergy in living organisms. Electromagnetic fields spreading, pesticide by-products and mixtures monitoring become greater for environmental contamination evaluations.

Cytotoxicity on Allium cepa of the two main sulcotrione photoproducts, xanthene-1,9-dione-3,4-dihydro-6-methylsulphonyl and 2-chloro-4-mesylbenzoic acid.

The cytotoxic effects of 2-chloro-4-mesylbenzoic acid (CMBA) and xanthene-1,9-dione-3,4-dihydro-6-methylsulphonyl (XDD), the two main photoproducts of sulcotrione, were investigated on Allium root meristematic cells at different concentrations. Degradation of sulcotrione was correlated to mitotic index decrease, together with increasing anomaly and c-mitosis frequencies. Mitotic index significantly decreased with increasing XDD and CMBA concentrations. Cell frequency with abnormal chromosomes increased with CMBA or XDD application rates. In contrast, CMBA induced a low micronucleus rate even for high concentrations while XDD increased the micronucleus ratio. C-mitoses, chromosomal aberrations due to an inactivation of the spindle, were enhanced by CMBA treatments but not by XDD. The photochemical degradation process of the pesticide can change the risk for the environment.

Toxicity of sulcotrione and grape marc on Vicia faba cells.

The cell toxicity of sulcotrione, a selective triketone herbicide, was evaluated on Vicia faba. Sulcotrione, trademark Mikado, grape marc, and mixtures of sulcotrione or Mikado with grape marc induced cell death. Addition of grape marc to either sulcotrione or Mikado enhanced cell death, especially with Mikado. Addition of grape marc to herbicides, sulcotrione, or Mikado resulted in different expression of genes usually associated with cell stress. Mixtures of grape marc and herbicides enhanced transcript accumulation for ubiquitin, hsp 70, and cytosolic superoxide dismutase, but did not change ascorbate peroxidase transcript accumulation. The results thus provide evidence that sulcotrione, Mikado, and mixtures with grape marc can trigger cell death and specific gene expressions. Cocktails of products with sulcotrione, such as commercial additives and grape marc, can modify biological features of pesticide. Moreover, grape marc differently enhanced cell toxicity of sulcotrione and Mikado, suggesting a synergy between pesticide products and grape marc.

Water extracts from winery by-products as tobacco defense inducers.

Water extracts from winery by-products exhibited significant plant defense inducer properties. Experiments were conducted on three marc extracts containing various amounts of polyphenols and anthocyanins. Infiltration of red, white and seed grape marc extracts into tobacco leaves induced hypersensitive reaction-like lesions with cell death evidenced by Evans Blue staining. The infiltration zones and the surrounding areas revealed accumulation of autofluorescent compounds under UV light. Leaf infiltration of the three winery by-product extracts induced defense gene expression. The antimicrobial PR1, ß-1,3-glucanase PR2, and chitinase PR3 target genes were upregulated locally in tobacco plants following grape marc extract treatments. The osmotin PR5 transcripts accumulated as well in red marc extract treated-tobacco leaves. Overall, the winery by-product extracts elicited an array of plant defense responses making the grape residues a potential use of high value compounds.

Genotoxicity of sulcotrione pesticide and photoproducts on Allium cepa root meristem.

Contamination by toxic agents in the environment has become matters of concern to agricultural countries. Sulcotrione, a triketone herbicide used to control dicotyledonous weeds in maize culture is rapidly photolyzed on plant foliage and generate two main photoproducts the xanthene-1,9-dione-3,4-dihydro-6-methylsulfonyl and 2-chloro-4-mesylbenzoic acid (CMBA). The aim of this study was to analyze the potential toxicity of the herbicide and the irradiated herbicide cocktail. Cytotoxicity and genotoxicity of non irradiated and irradiated sulcotrione were investigated in Allium cepa test. The sulcotrione irradiation was monitored under sunlight simulated conditions to reach 50% of phototransformation. Concentrations of sulcotrione in the range 5 × 10(-)(9)-5 × 10(-)(5)M were tested. Cytological analysis of root tips cells showed that both non irradiated and irradiated sulcotrione caused a dose-dependent decrease of mitotic index with higher cytotoxicity for the irradiated herbicide which can lead to 24.2% reduction of mitotic index compared to water control. Concomitantly, chromosomal aberrations were observed in A.cepa root meristems. Both non irradiated sulcotrione and irradiated sulcotrione induced a dose-dependent increase of chromosomal abnormalities frequencies to a maximal value of 33.7%. A saturating effect in anomaly frequencies was observed in meristems treated with high concentrations of non irradiated sulcotrione only. These data suggest that photolyzed sulcotrione cocktail have a greater cytotoxicity and genotoxicity than parent molecule and question about the impact of photochemical process on environment.