5,6-difluorogramine And Its Analogues: Synthesis、Marine Antifouling Activity In And Potential Ecological Risk

The organic biocides which are incorporated into antifouling paints play important role in the fight against marine biofouling attachment, and meanwhile have a potential negative impact on the marine organisms and food safety. Two new antifouling agent 5,6-difluorogramine(DFG)and 3,4-dichlorophenyl-N,N-dimethylmethanamine(DCDMA) were analysised in this paper. All title compounds are identified by means of FTIR and NMR. The optimum conditions of these new products are studied respectively, and the influence factors of reactions involved are discussed respectively also. The antifouling properties of two new anti-fouling agents were carried out by the experiments of antibacterial,micro-algal inhibition and mussels inhibition. Their safety to marine organisms were studied by short-term acute toxicity of Sebastiscus marmoratus(Cuvier) and mouse.(1)In the work, the antimicrobial activity,micro-algal inhibition and mussels inhibition of DFG and DCDMA was studied.The results showed that IC50 value to w-1(Pseudomonas stutzeri) and F-6(Bacillus cereus) was respectively: DFG: 0.726 mg·m L-1 and 0.602 mg·m L-1, DCDMA: 0.214 mg·m L-1 and 0.732 mg·m L-1, with the banned antifoulant TBTO as control: 0.0822 μg·m L-1 and 0.0692 μg·m L-1. The range of MIC value for inhibition to Chlorella vulgaris Beij and Chlamydomonas reinhardtii was respectively: DFG: 2~3 μg·m L-1 and >3 μg·m L-1, DCDMA: 1~2 μg·m L-1(both), while the banned TBTO: 0.1~0.5 μg·m L-1 and <0.1 μg·m L-1, and up-to-now used herbicide antifouling agent diuron: 0.1μg·m L-1 and 0.1~0.5 μg·m L-1. According to the relationship between the number of mussel byssus secretion and antifouling agent concentration,The results showed : TBTO>Diuron>TGB>DCDMA.(2)With Cuvier exposure to test solutions of DFG and DCDMA respectively, LC50 values for 96 h were gotten between1.0 mg·L-1 and 10.0 mg·L-1, and the safe concentrations were respectively 1.22 mg·L-1and 2.80 mg·L-1. According to Test method of fish acute toxicity fro dangerous chemical products GB/T 21281-2007, the two novel antifouling agents belonged to acute toxicity grade II. LD50 of DFG and DCDMA was measured by intraperitoneal injection to mouse, which was 132.205 and 24.118 mg·kg-1, respectively.The results provide the application performance and the safety performance of the data used for antifouling agents.