We study the pseudo-differential operator \begin{equation*} T_a f\left(x\right)=\int_{^n}e^{ix\cdot\xi}a\left(x,\xi\right)\widehat{f}\left(\xi\right),\xi, \end{equation*} where the symbol is in the H"{o}rmander class or more generally in the rough H"{o}rmander class with and . It is known that is bounded on for . In this paper we mainly investigate its boundedness properties when is equal to the critical index . For any we construct a symbol $a\in S^{n(\rho-1)}{\rho,1}T_aL^1$ and furthermore it is not of weak type if . On the other hand we prove that is bounded from to if and construct a symbol such that is unbounded from to . Finally, as a complement, for any we give an example $a\in S^{-1/p}{0,1}T_aL^p()$.

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