The paper presents the evaluation of effectiveness of deep chiseling with the help of analytical methods. General objective of the work is to develop the method for describing theoretical interaction of operating parts of machines and tools with soil during main chiseling in the form of a stochastic process of successive hits of the operating part with a solid medium. The destruction of monoliths (uncultivated) soil during its cultivation was considered as a process of formation and subsequent evolution of dynamic cracks, the nature and amount of which, in a particular soil volume, is determined by the amount of energy absorbed by operating parts and the actual properties of cultivated soil. It should be taken into consideration that the spread of cracks during chiseling occurs by the lowest strength of connections between certain structural units, in fact organic inclusions, soil pores, moisture inclusions and other similar elements are the largest centers of formation, concentration and further development of cracks during cultivation. Interaction of operating parts of machines and tools with soil is most expedient to carry out modeling work in a thickness of the environment of a dihedral wedge taking into account mechanical structure of soil. It is established that the number of cracks and the size and number of lumps after cultivation are linearly dependent, which means that to qualitatively study the change in physical state, during chiseling with operating parts and tools, it is enough to study the process and evolution of cracking. As a result of the work performed, it is proved that the degree of soil grinding during its chiseling can be assessed by probability, and the quality of tools, that is the percentage of total mass of cultivated soil particles with the size not exceeding 50 mm. When modeling chiseling, the grinding process can be considered in the form of interaction of a dihedral wedge with a solid structured layer of soil with specified properties. The interaction of the chiseling operating part with the soil is accompanied by deformation of soil environment, increased stresses and cracks, which ultimately determine the shape and size of the crushed units. We believe that the number and nature of cracks that occur during tillage are in direct proportion to the size of the obtained units upon completion.