| Summary: | The secondary metabolites of the phytopathogenic fungus <i>Corynespora cassiicola</i> CC01 from <i>Hevea brasiliensis</i> were investigated. As a result, two new compounds, 5-acetyl-7-hydroxy-6- methoxybenzofuran-2(3<i>H</i>)-one (<b>1</b>) and (<i>S</i>)-2-(2,3-dihydrofuro [3,2-<i>c</i>]pyridin-2-yl)propan-2-ol (<b>2</b>), together with seven known compounds, 4,6,8-trihydroxy-3,4-dihydronaphthalen-1(2<i>H</i>)-one (<b>3</b>), 3,6,8-trihydroxy-3,4-dihydronaphthalen-1(2<i>H</i>)-one (<b>4</b>), curvulin acid (<b>5</b>), 2-methyl-5-carboxymethyl- 7-hydroxychromone (<b>6</b>), tyrosol (<b>7</b>), <i>p</i>-hydroxybenzoic acid (<b>8</b>) and cerevisterol (<b>9</b>), were isolated from the fermentation extract by comprehensive silica gel, reverse phase silica gel, Sephadex-LH20 column chromatography and high-performance liquid chromatography (HPLC). The structures of these compounds were identified by using high-resolution electrospray mass spectrometry (HRESIMS), nuclear magnetic resonance spectroscopy (NMR), optical rotation, ultraviolet and infrared spectroscopy techniques and a comparison of NMR data with those reported in the literature. Compounds <b>1</b> and <b>2</b> were new compounds, and compounds <b>3</b>–<b>9</b> were discovered from this phytopathogenic fungus for the first time. Compounds <b>1</b>–<b>9</b> were tested for phytotoxicity against the fresh tender leaf of <i>Hevea brasiliensis</i>, and the results show that none of them were phytotoxic. Additionally, these compounds were subjected to an antimicrobial assay against three bacteria (<i>E. coli</i>, <i>methicillin-resistant Staphylococcus aureus</i> and <i>Micrococcus luteus</i>), but they showed no activity.
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