Aromatic amides having a fungicidal activity, their agronomic compositions and relative preparation method

Abstract

Aromatic amides are described, having general formula (I): ##STR00001##
suitably substituted and having a high fungicidal activity, together with their use for controlling phytopathogenic fungi of important agricultural crops.

Claims

1. An amide having general formula (I): ##STR00419## wherein: R.sup.1 represents a C.sub.1-C.sub.12 alkoxyl, a C.sub.1-C.sub.12 haloalkoxyl, a C.sub.3-C.sub.18 cycloalkoxyl, a —NR.sup.4R.sup.5 group; R.sup.2 represents a C.sub.2-C.sub.13 acyl, a C.sub.2-C.sub.12 alkanoyloxyalkyl C.sub.1-C.sub.12, a C.sub.2-C.sub.12 haloalkanoyloxyalkyl C.sub.1-C.sub.12, a C.sub.1-C.sub.12 alkoxy-C.sub.1-C.sub.12-alkanoyloxyalkyl C.sub.1-C.sub.12, a C.sub.1-C.sub.12 haloalkoxy-C.sub.1-C.sub.12-alkanoyloxyalkyl C.sub.1-C.sub.12, a C.sub.3-C.sub.18 cycloalkoxy-C.sub.1-C.sub.12-alkanoyloxyalkyl C.sub.1-C.sub.12, an aryloxy C.sub.1-C.sub.12 alkanoyloxyalkyl C.sub.1-C.sub.12, a benzyloxy C.sub.1-C.sub.12 alkanoyloxyalkyl C.sub.1-C.sub.12, a C.sub.4-C.sub.18 cycloalkanoyloxyalkyl C.sub.1-C.sub.12, a C.sub.1-C.sub.12 aroyloxyalkyl, a C.sub.1-C.sub.12 benzoyloxyalkyl, a C.sub.1-C.sub.12 heterocyclylcarbonyloxyalkyl, a C.sub.1-C.sub.12 alkyloxyalkyl C.sub.1-C.sub.12, a C.sub.1-C.sub.12 haloalkyloxyalkyl C.sub.1-C.sub.12, a C.sub.1-C.sub.12 alkoxy-C.sub.1-C.sub.12-alkyloxyalkyl C.sub.1-C.sub.12, a C.sub.1-C.sub.12 haloalkoxy-C.sub.1-C.sub.12-alkyloxyalkyl C.sub.1-C.sub.12, a C.sub.3-C.sub.18 cycloalkoxy C.sub.1-C.sub.12-alkyloxyalkyl C.sub.1-C.sub.12, an aryloxy C.sub.1-C.sub.12-alkyloxyalkyl C.sub.1-C.sub.12, a benzyloxy C.sub.1-C.sub.12-alkyloxyalkyl C.sub.1-C.sub.12, a C.sub.3-C.sub.18 cycloalkyloxyalkyl C.sub.1-C.sub.12, a C.sub.1-C.sub.12 aryloxyalkyl, a C.sub.1-C.sub.12 benzyloxyalkyl; a C.sub.1-C.sub.12 heterocyclyloxyalkyl, a C.sub.4-C.sub.12 alkanoylthioalkyl C.sub.1-C.sub.12, a C.sub.2-C.sub.12 haloalkanoylthioalkyl C.sub.1-C.sub.12, a C.sub.4-C.sub.18 cycloalkanoylthioalkyl C.sub.1-C.sub.12, a C.sub.1-C.sub.12 aroylthioalkyl, a C.sub.1-C.sub.12 benzoylthioalkyl; a C.sub.1-C.sub.12 heterocyclylcarbonylthioalkyl, a C.sub.1-C.sub.12 alkylthioalkyl C.sub.1-C.sub.12, a C.sub.1-C.sub.12 haloalkylthioalkyl C.sub.1-C.sub.12, a C.sub.1-C.sub.12 alkoxy-C.sub.1-C.sub.12-alkylthioalkyl C.sub.1-C.sub.12, a C.sub.1-C.sub.12 haloalkoxy-C.sub.1-C.sub.12-alkylthioalkyl C.sub.1-C.sub.12, a C.sub.3-C.sub.18 cycloalkoxy C.sub.1-C.sub.12-alkylthioalkyl C.sub.1-C.sub.12, a C.sub.1-C.sub.12 aryloxy alkylthioalkyl C.sub.1-C.sub.12, a C.sub.1-C.sub.12 benzyloxy alkylthioalkyl C.sub.1-C.sub.12, a C.sub.3-C.sub.18 cycloalkylthioalkyl C.sub.1-C.sub.12, a C.sub.1-C.sub.12 benzylthioalkyl, a C.sub.1-C.sub.12 arylthioalkyl, a C.sub.1-C.sub.12 heterocyclylthioalkyl, a C.sub.2-C.sub.12 alkanoylaminoalkyl C.sub.1-C.sub.12, a C.sub.2-C.sub.12 haloalkanoylaminoalkyl C.sub.1-C.sub.12, a C.sub.4-C.sub.18 cycloalkanoylaminoalkyl C.sub.1-C.sub.12, a C.sub.1-C.sub.12 aroylaminoalkyl, a C.sub.1-C.sub.12 benzoylaminoalkyl, a C.sub.1-C.sub.12 heterocyclylcarbonylaminoalkyl, a C.sub.1-C.sub.12 heterocyclylaminoalkyl, a C.sub.4-C.sub.18 cycloalkylaminoalkyl C.sub.1-C.sub.12, a tetrahydropyranyl, a C.sub.1-C.sub.12 trimethylsilyloxyalkyl, a C.sub.1-C.sub.12 trimethylsilyl-ethoxyalkyl; R.sup.1 and R.sup.2 together with the carbon atoms to which they are bound can form a 1,3-oxazole ring; R.sup.3 represents a hydrogen atom, a C.sub.1-C.sub.12 alkyl, a C.sub.3-C.sub.18 cycloalkyl; R.sup.4 and R.sup.5, the same or different, represent a hydrogen atom, an aminocarbonyl group, a methylaminocarbonyl group, a dimethylaminocarbonyl group, a C.sub.1-C.sub.12 alkyl, a formyl, a C.sub.2-C.sub.13 acyl, a C.sub.2-C.sub.13 haloalkylcarbonyl, a benzyl group, an aroyl group, a C.sub.2-C.sub.13 alkoxycarbonyl, a C.sub.1-C.sub.12 alkoxyalkyl C.sub.1-C.sub.12; a C.sub.1-C.sub.12 alkanoyloxyalkyl C.sub.1-C.sub.12, a C.sub.1-C.sub.12 haloalkanoyloxyalkyl C.sub.1-C.sub.12, a C.sub.3-C.sub.18 cycloalkanoyloxyalkyl C.sub.1-C.sub.12, a C.sub.1-C.sub.12 aroyloxyalkyl, a C.sub.1-C.sub.12 heterocyclylcarbonyloxyalkyl, a C.sub.1-C.sub.12 aryloxyalkyl, a C.sub.1-C.sub.12 heterocyclyloxyalkyl, a C.sub.1-C.sub.12 alkanoylthioalkyl C.sub.1-C.sub.12, a C.sub.1-C.sub.12 halo-alkanoylthioalkyl C.sub.1-C.sub.12, a C.sub.3-C.sub.18 cycloalkanoylthioalkyl C.sub.1-C.sub.12, a C.sub.1-C.sub.12 aroylthioalkyl, a C.sub.1-C.sub.12 heterocyclylthioalkyl, a C.sub.1-C.sub.12 arylthioalkyl, a C.sub.1-C.sub.12 alkanoylaminoalkyl C.sub.1-C.sub.12, a C.sub.1-C.sub.12 haloalkanoylaminoalkyl C.sub.1-C.sub.12, a C.sub.3-C.sub.18 cycloalkanoylaminoalkyl C.sub.1-C.sub.12, a C.sub.1-C.sub.12 aroylaminoalkyl, a C.sub.1-C.sub.12 heterocyclylaminoalkyl; A represents a direct bond or a C.sub.1-C.sub.12 alkyl; Y represents an oxygen or sulfur atom; Z represents an oxygen or sulfur atom; X represents a halogen atom, a CN group, a NO.sub.2 group; n represents a number ranging from 0 to 3; G represents a C.sub.3-C.sub.18 cycloalkyl containing from 0 to 3 heteroatoms selected from the group consisting of O, N, S, a C.sub.3-C.sub.18 cycloalkenyl containing from 1 to 3 unsaturations and from 0 to 3 heteroatoms selected from the group consisting of O, N, S, a C.sub.6-C.sub.20 bicycloalkyl containing from 0 to 3 heteroatoms selected from O, N, S, a C.sub.6-C.sub.20 bicycloalkenyl containing from 1 to 3 unsaturations and from 0 to 3 heteroatoms selected from the group consisting of O, N, S, adamantyl, said cyclic groups being optionally substituted with 1 to 3 groups, the same or different, selected from the group consisting of C.sub.1-C.sub.6 alkyl, C.sub.3-C.sub.12 cycloalkyl, benzyl and with the possibility of incorporating in said cyclic structure one or more groups selected from the group consisting of: C═O, C(═O)O, C(═O)S, C(═S)O, C(═S)S, C(═O)NR.sup.3; with the proviso that if R.sup.1 represents a —NR.sup.4R.sup.5 group wherein R.sup.4 is a hydrogen atom and R.sup.5 is an aminocarbonyl group, a methylaminocarbonyl group, a dimethylaminocarbonyl group, a formyl, a C.sub.2-C.sub.13 acyl, a C.sub.2-C.sub.13 alkoxycarbonyl, and R.sup.2 and R.sup.3 represent a hydrogen atom, and Y is an oxygen atom, G cannot be a C.sub.3-C.sub.12 cycloalkyl, a C.sub.3-C.sub.12 cycloalkenyl and a C.sub.3-C.sub.8 cycloalkyl containing from 0 to 3 heteroatoms selected from O, N, S.

2. The amide according to claim 1, wherein: R.sup.1 represents a C.sub.1-C.sub.6 alkoxyl, a C.sub.1-C.sub.6 haloalkoxyl, a C.sub.3-C.sub.12 cycloalkoxyl, a —NR.sup.4R.sup.5 group; R.sup.2 represents a C.sub.2-C.sub.7 acyl, a C.sub.2-C.sub.7 alkanoyloxyalkyl C.sub.1-C.sub.6, a C.sub.2-C.sub.7 haloalkanoyloxyalkyl C.sub.1-C.sub.6, a C.sub.1-C.sub.6 alkoxy-C.sub.1-C.sub.6-alkanoyloxyalkyl C.sub.1-C.sub.6, a C.sub.1-C.sub.6 haloalkoxy-C.sub.1-C.sub.6-alkanoyloxyalkyl C.sub.1-C.sub.6, a C.sub.3-C.sub.12 cycloalkoxy-C.sub.1-C.sub.6-alkanoyloxyalkyl C.sub.1-C.sub.6, an aryloxy C.sub.1-C.sub.6 alkanoyloxyalkyl C.sub.1-C.sub.6, a benzyloxy C.sub.1-C.sub.6 alkanoyloxyalkyl C.sub.1-C.sub.6, a C.sub.4-C.sub.12 cycloalkanoyloxyalkyl C.sub.1-C.sub.6, a C.sub.1-C.sub.6 aroyloxyalkyl, a C.sub.1-C.sub.6 benzoyloxyalkyl, a C.sub.1-C.sub.6 heterocyclylcarbonyloxyalkyl, a C.sub.1-C.sub.6 alkyloxyalkyl C.sub.1-C.sub.6, a C.sub.1-C.sub.6 haloalkyloxyalkyl C.sub.1-C.sub.6, a C.sub.1-C.sub.6 alkoxy-C.sub.1-C.sub.6-alkyloxyalkyl C.sub.1-C.sub.6, a C.sub.1-C.sub.6 haloalkoxy-C.sub.1-C.sub.6-alkoxyalkyl C.sub.1-C.sub.6, a C.sub.3-C.sub.12 cycloalkoxy C.sub.1-C.sub.6-alkyloxyalkyl C.sub.1-C.sub.6, an aryloxy C.sub.1-C.sub.6-alkyloxyalkyl C.sub.1-C.sub.6, a benzyloxy C.sub.1-C.sub.6-alkyloxyalkyl C.sub.1-C.sub.6, a C.sub.3-C.sub.12 cycloalkyloxyalkyl C.sub.1-C.sub.6, a C.sub.1-C.sub.6 aryloxyalkyl, a C.sub.1-C.sub.6 benzyloxyalkyl; a C.sub.1-C.sub.6 heterocyclyloxyalkyl, a C.sub.4-C.sub.6 alkanoylthioalkyl C.sub.1-C.sub.6, a C.sub.2-C.sub.6 haloalkanoylthioalkyl C.sub.1-C.sub.6, a C.sub.4-C.sub.12 cycloalkanoylthioalkyl C.sub.1-C.sub.6, a C.sub.1-C.sub.6 aroylthioalkyl, a C.sub.1-C.sub.6 benzoylthioalkyl; a C.sub.1-C.sub.6 heterocyclylcarbonylthioalkyl, a C.sub.1-C.sub.6 alkylthioalkyl C.sub.1-C.sub.6, a C.sub.1-C.sub.6 haloalkylthioalkyl C.sub.1-C.sub.6, a C.sub.1-C.sub.6 alkoxy-C.sub.1-C.sub.6-alkylthioalkyl C.sub.1-C.sub.6, a C.sub.1-C.sub.6 haloalkoxy-C.sub.1-C.sub.6-alkylthioalkyl C.sub.1-C.sub.6, a C.sub.3-C.sub.12 cycloalkoxy C.sub.1-C.sub.6 alkylthioalkyl C.sub.1-C.sub.6, a C.sub.1-C.sub.6 aryloxy alkylthioalkyl C.sub.1-C.sub.6, a C.sub.1-C.sub.6 benzyloxy alkylthioalkyl C.sub.1-C.sub.6, a C.sub.3-C.sub.12 cycloalkylthioalkyl C.sub.1-C.sub.6, a C.sub.1-C.sub.6 benzylthioalkyl, a C.sub.1-C.sub.6 arylthioalkyl, a C.sub.1-C.sub.6 heterocyclylthioalkyl, a C.sub.2-C.sub.6 alkanoylaminoalkyl C.sub.1-C.sub.6, a C.sub.2-C.sub.6 haloalkanoylaminoalkyl C.sub.1-C.sub.6, a C.sub.4-C.sub.12 cycloalkanoylaminoalkyl C.sub.1-C.sub.6, a C.sub.1-C.sub.6 aroylaminoalkyl, a C.sub.1-C.sub.6 benzoylaminoalkyl, a C.sub.1-C.sub.6 heterocyclylcarbonylaminoalkyl, a C.sub.1-C.sub.6 heterocyclylaminoalkyl, a C.sub.4-C.sub.12 cycloalkylaminoalkyl C.sub.1-C.sub.6, a tetrahydropyranyl, a C.sub.1-C.sub.6 trimethylsilyloxyalkyl, a C.sub.1-C.sub.6 trimethylsilyl-ethoxyalkyl; R.sup.3 represents a hydrogen atom, a C.sub.1-C.sub.6 alkyl, a C.sub.3-C.sub.12 cycloalkyl; R.sup.4 and R.sup.5, the same or different, represent a hydrogen atom, an aminocarbonyl group, a methylaminocarbonyl group, a dimethylaminocarbonyl group, a C.sub.1-C.sub.6 alkyl, a formyl, a C.sub.2-C.sub.7 acyl, a C.sub.2-C.sub.7 haloalkylcarbonyl, a benzyl group, an aroyl group, a C.sub.2-C.sub.7 alkoxycarbonyl, a C.sub.1-C.sub.6 alkoxyalkyl C.sub.1-C.sub.6; a C.sub.1-C.sub.6 alkanoyloxyalkyl C.sub.1-C.sub.6, a C.sub.1-C.sub.6 haloalkanoyloxyalkyl C.sub.1-C.sub.12, a C.sub.3-C.sub.12 cycloalkanoyloxyalkyl C.sub.1-C.sub.6, a C.sub.1-C.sub.6 aroyloxyalkyl, a C.sub.1-C.sub.6 heterocyclylcarbonyloxyalkyl, a C.sub.1-C.sub.6 aryloxyalkyl, a C.sub.1-C.sub.6 heterocyclyloxyalkyl, a C.sub.1-C.sub.6 alkanoylthioalkyl C.sub.1-C.sub.6, a C.sub.1-C.sub.6 haloalkanoylthioalkyl C.sub.1-C.sub.6, a C.sub.3-C.sub.12 cycloalkanoylthioalkyl C.sub.1-C.sub.6, a C.sub.1-C.sub.6 aroylthioalkyl, a C.sub.1-C.sub.6 heterocyclylthioalkyl, a C.sub.1-C.sub.6 arylthioalkyl, a C.sub.1-C.sub.6 alkanoylaminoalkyl C.sub.1-C.sub.6, a C.sub.1-C.sub.6 haloalkanoylaminoalkyl C.sub.1-C.sub.6, a C.sub.3-C.sub.12 cycloalkanoylaminoalkyl C.sub.1-C.sub.6, a C.sub.1-C.sub.6 aroylaminoalkyl, a C.sub.1-C.sub.6 heterocyclylaminoalkyl; A represents a direct bond or a C.sub.1-C.sub.6 alkyl; Y represents an oxygen or sulfur atom; X represents a halogen atom, a CN group, a NO.sub.2 group; n represents a number ranging from 0 to 1; G represents a C.sub.3-C.sub.12 cycloalkyl containing from 0 to 3 heteroatoms selected from O, N, S, a C.sub.3-C.sub.12 cycloalkenyl containing from 1 to 3 unsaturations and from 0 to 3 heteroatoms selected from the group consisting of O, N, S, a C.sub.6-C.sub.16 bicycloalkyl containing from 0 to 3 heteroatoms selected from O, N, S, a C.sub.6-C.sub.16 bicycloalkenyl containing from 1 to 3 unsaturations and from 0 to 3 heteroatoms selected from O, N, S, adamantyl, said cyclic groups being optionally substituted with 1 to 3 groups, the same or different, selected from the group consisting of C.sub.1-C.sub.6 alkyl, C.sub.3-C.sub.12 cycloalkyl, benzyl and with the possibility of incorporating in said cyclic structure one or more groups selected from the group consisting of: C═O, C(═O)O, C(═O)S, C(═S)O, C(═S)S, and C(═O)NR.sup.3.

3. The amide according to claim 1, wherein: R.sup.2 represents a C.sub.2-C.sub.6 acyl, a C.sub.1-C.sub.6 alkoxy-C.sub.1-C.sub.6-alkanoyloxyalkyl C.sub.1-C.sub.6, a C.sub.1-C.sub.6 haloalkoxy-C.sub.1-C.sub.6-alkanoyloxyalkyl C.sub.1-C.sub.6, a C.sub.3-C.sub.12 cycloalkoxy-C.sub.1-C.sub.6-alkanoyloxyalkyl C.sub.1-C.sub.6, a C.sub.3-C.sub.12 cycloalkyloxyalkyl C.sub.1-C.sub.6, a C.sub.4-C.sub.12 alkanoylthioalkyl C.sub.1-C.sub.6, a C.sub.2-C.sub.6 haloalkanoylthioalkyl C.sub.1-C.sub.6, a C.sub.4-C.sub.12 cycloalkanoylthioalkyl C.sub.1-C.sub.6, a C.sub.2-C.sub.6 alkanoylaminoalkyl C.sub.1-C.sub.6, a C.sub.2-C.sub.6 haloalkanoylaminoalkyl C.sub.1-C.sub.6, a C.sub.1-C.sub.6 alkoxy-C.sub.1-C.sub.6-alkyloxyalkyl C.sub.1-C.sub.6, a C.sub.1-C.sub.6 haloalkoxy-C.sub.1-C.sub.6-alkyloxyalkyl C.sub.1-C.sub.6, a C.sub.3-C.sub.12 cycloalkoxy C.sub.1-C.sub.6-alkyloxyalkyl C.sub.1-C.sub.6, a tetrahydropyranyl, a C.sub.1-C.sub.6 trimethylsilyloxyalkyl, a C.sub.1-C.sub.6 trimethylsilyl-ethoxyalkyl; Y and Z both represent an oxygen atom; G represents a C.sub.3-C.sub.12 cycloalkyl containing from 0 to 3 heteroatoms selected from O, N, S, a C.sub.3-C.sub.12 cycloalkenyl containing from 1 to 3 unsaturations and from 0 to 3 heteroatoms selected from the group consisting of O, N, S, a C.sub.6-C.sub.16 bicycloalkyl containing from 0 to 3 heteroatoms selected from the group consisting of O, N, S, a C.sub.6-C.sub.16 bicycloalkenyl containing from 1 to 3 unsaturations and from 0 to 3 heteroatoms selected from the group consisting of O, N, S, adamantyl, said cyclic groups being optionally substituted with 1 to 3 groups, the same or different, selected from the group consisting of C.sub.1-C.sub.6 alkyl, C.sub.3-C.sub.12 cycloalkyl, benzyl and with the possibility of incorporating in said cyclic structure one or more groups selected from the group consisting of: C═O, C(═O)O, C(═O)S, C(═S)O, C(═S)S, and C(═O)NR.sup.3.

4. The amide according to claim 1, selected from compounds having general formula (I) wherein R.sup.1, R.sup.2, R.sup.3, Y, Z, X, n, A, G have the meanings indicated in the following table TABLE-US-00008 Comp. R.sup.1 R.sup.2 R.sup.3 Y Z A X n G 1. NHCHO H O O — 0 2. NHCHO H O O — 0 3. NHCHO H O O — 0 4. NR.sup.2CHO H O O — 0 5. NR.sup.2CHO H O O — 0 6. NR.sup.2CHO H O O — 0 7. NR.sub.2.sup.2 H O O — 0 8. NR.sub.2.sup.2 H O O — 0 9. NR.sub.2.sup.2 H O O — 0 10. NHCHO H O O — 0 11. NHCHO H O O — 0 12. NHCHO H O O — 0 13. NHCHO H O O — 0 14. NHCHO H O O — 0 15. NHCHO H O O — 0 16. NHCHO H O O — 0 17. NHCHO H O O — 0 18. NHCHO H O O — 0 19. NHCHO H O O — 0 20. NHCHO CH.sub.3 O O — 0 21. NHCHO CH.sub.3 O O — 0 22. NHCHO CH.sub.3 O O — 0 23. NHCHO H S O — 0 24. OCH.sub.3 H S O — 0 25. NHCHO H S O — 0 26. NHCHO H O O — 0 27. NHCHO H O O — 0 28. NHCHO H O O — 0 29. NHCHO H O O — 0 30. NHCHO H O O — 0 31. NHCHO H O O CH.sub.2 0 32. NHCHO H O O CH.sub.2 0 33. OCH.sub.3 H O O — 5-Cl 1 34. OCH.sub.3 H O O — 6-Br 1 35. OCH.sub.3 H O O — 4-NO.sub.2 1 36. NHCHO H O O CH.sub.2 0 37. NHCHO H O O CH.sub.2 0 38. NHCHO H O O CH.sub.2 0 39. NHCHO H O O — 0 40. NHCHO H O O — 0 41. NHCHO H S O 0 42. NHCHO H S O — 0 43. NHCHO H O O — 0 44. NHCHO H S O — 0 45. NHCHO H O O — 0 46. NHCHO H O O — 0 47. NHCHO H O O — 0 48. NHCHO H S O — 0 49. NHCHO H O O — 0 50. NHCHO H O O — 0 52. NHCHO COCH.sub.3 H O O — 0 53. NHCHO H O O — 0 54. NHCHO H O O — 0 55. NHCHO H O O — 0 56. NHCHO H O O — 0 57. NHCHO H O O — 0 58. NHCHO H O O — 0 59. NHCHO H O O — 0 60. NHCHO H O O — 0 61. NHCHO H O O — 0 62. NHCHO H O O — 0 63. NHCHO H O O — 0 64. NHCHO H S O — 0 65. NHCHO H O O — 0 66. NHCHO H O O — 0 67. NHCHO H O O — 0 68. NHCHO H O O — 0 69. NHCHO H O O — 0 70. NHCHO H O O CH.sub.2 0 72. NHCHO COCH.sub.3 H O O — 0 73. NHCHO H O O — 0 74. NHCHO H O O — 0 75. NHCHO H O O — 0 77. NHCHO COCH.sub.3 H O O — 0 78. NHCHO H O O — 0 79. NHCHO H O O — 0 80. NHCHO H O O — 0 82. NHCHO COCH.sub.3 H O O — 0 83. NHCHO H O O — 0 84. NHCHO H O O — 0 85. NHCHO H O O — 0 87. NHCHO H O O — 0 88. NHCHO COCH.sub.3 H O O — 0 89. NHCHO H O O — 0 90. NHCHO H O O — 0 91. NHCHO H O S — 0 92. NHCHO H O S — 0 93. NHCHO H O S — 0 94. NHCHO H O S — 0 95. NHCHO H O S — 0 96. NHCHO H O S — 0 97. NHCHO H O S — 0 98. NHCHO H O S — 0 99. NHCHO H O S — 0 100. NHCHO H O S — 0 101. NHCHO COCH.sub.3 H O S — 0 102. NHCHO H O S — 0 103. NHCHO COCH.sub.3 H O S — 0 104. NHCHO H O S — 0 105. NHCHO H O S — 0 106. NHCHO COCH.sub.3 H O S — 0 107. NHCHO COCH.sub.3 H O S — 0

5. The amide according to claim 1, selected from compounds having general formula (I) wherein R.sup.1, R.sup.2, R.sup.3, Y, Z, X, n, A, G have the meanings indicated in the following table TABLE-US-00009 Comp. R.sup.1 R.sup.2 R.sup.3 Y Z A X n G 1. NHCHO H O O — 0 2. NHCHO H O O — 0 4. NR.sup.2CHO H O O — 0 10. NHCHO H O O — 0 106. NHCHO COCH.sub.3 H O S — 0 107. NHCHO COCH.sub.3 H O S — 0

6. The amide according to claim 1, which are a) geometric isomers of the compounds having general formula (I); b) in the form of salts of the compounds having formula (I) obtained by the addition of inorganic or organic acids; c) hydrated forms of the compounds having formula (I).

7. A fungicidal composition comprising at least one compound having formula (I) according to claim 1, a solvent and/or solid or liquid diluent, and optionally a surfactant.

8. The composition according to claim 7, comprising one or more further active ingredients selected from the group consisting of fungicides other than those having general formula (I), phytoregulators, antibiotics, herbicides, insecticides, fertilizers and/or mixtures thereof, preferably comprising at least one other fungicide.

9. The composition according to claim 8, consisting of a compound having formula (I) and a further fungicide, selected from the group consisting of: C1: compound 1+tetraconazole; C2: compound 1+tebuconazole; C3: compound 1+epoxyconazole; C4: compound 1+prothioconazole; C5: compound 1+difenoconazole; C6: compound 1+penconazole; C7: compound 1+prochloraz; C8: compound 1+fenpropimorph; C9: compound 1+spiroxamine; C10: compound 1+bixafen; C11: compound 1+boscalid; C12: compound 1+carboxin; C13: compound 1+fluopyram; C14: compound 1+fluxapyroxad; C15: compound 1+isopyrazam; C16: compound 1+penthiopyrad; C17: compound 1+sedaxane; C18: compound 1+azoxystrobin; C19: compound 1+dimoxystrobin; C20: compound 1+fluoxastrobin; C21: compound 1+kresoxim-methyl; C22 compound 1+picoxystrobin; C23: compound 1+pyraclostrobin; C24: compound 1+trifloxystrobin; C25: compound 1+metrafenone; C26: compound 1+proquinazid; C27: compound 1+mepanipyrim; C28: compound 1+cyprodinil; C29: compound 1+iprodione; C30: compound 1+procymidone; C31: compound 1+carbendazim; C32: compound 1+thiophanate-methyl; C33: compound 1+fluindapyr; C34: compound 1+benalaxyl-M; C35: compound 1+fenpyrazamine; C36: compound 1+fluazinam; C37: compound 1+tolclofos-methyl; C38: compound 1+mandipropamid; C39: compound 1+copper oxychloride; C40: compound 1+copper salicylate; C41: compound 1+chlorothalonil; C42: compound 1+cimoxanil; C43: compound 1+dimetomorph; C44: compound 1+oxathiapiprolin; C45: compound 1+fluopicolide; C46: compound 2+tetraconazole; C47: compound 2+tebuconazole; C48: compound 2+epoxyconazole; C49: compound 2+prothioconazole; C50: compound 2+difenoconazole; C51: compound 2+penconazole; C52: compound 2+prochloraz; C53: compound 2+fenpropimorph; C54: compound 2+spiroxamine; C55: compound 2+bixafen; C56: compound 2+boscalid; C57: compound 2+carboxin; C58: compound 2+fluopyram; C59: compound 2+fluxapyroxad; C60: compound 2+isopyrazam; C61: compound 2+penthiopyrad; C62: compound 2+sedaxane; C63: compound 2+azoxystrobin; C64: compound 2+dimoxystrobin; C65: compound 2+fluoxastrobin; C66: compound 2+kresoxim-methyl; C67: compound 2+picoxystrobin; C68: compound 2+pyraclostrobin; C69: compound 2+trifloxystrobin; C70: compound 2+metrafenone; C71: compound 2+proquinazid; C72: compound 2+mepanipyrim; C73: compound 2+cyprodinil; C74: compound 2+iprodione; C75: compound 2+procymidone; C76: compound 2+carbendazim; C77: compound 2+thiophanate-methyl; C78: compound 2+fluindapyr; C79: compound 2+benalaxyl-M; C80: compound 2+fenpyrazamine; C81: compound 2+fluazinam; C82: compound 2+tolclofos-methyl; C83: compound 2+mandipropamid; C84: compound 2+copper oxychloride; C85: compound 2+copper salicylate; C86: compound 2+chlorothalonil; C87: compound 2+cimoxanil; C88: compound 2+dimetomorph; C89: compound 2+oxathiopiproline; C90: compound 2+fluopicolide; C91: compound 4+tetraconazole; C92: compound 4+tebuconazole; C93: compound 4+epoxyconazole; C94: compound 4+prothioconazole; C95: compound 4+difenconazole; C96: compound 4+penconazole; C97: compound 4+prochloraz; C98: compound 4+fenpropimorph; C99: compound 4+spiroxamine; C100: compound 4+bixafen; C101: compound 4+boscalid; C102: compound 4+carboxin; C103: compound 4+fluopyram; C104: compound 4+fluxapyroxad; C105: compound 4+isopyrazam; C106: compound 4+penthiopyrad; C107: compound 4+sedaxane; C108: compound 4+azoxystrobin; C109: compound 4+dimoxystrobin; C110: compound 4+fluoxastrobin; C111: compound 4+kresoxim-methyl; C112: compound 4+picoxystrobin; C113: compound 4+pyraclostrobin; C114: compound 4+trifloxystrobin; C115: compound 4+metrafenone; C116: compound 4+proquinazid; C117: compound 4+mepanipyrim; C118: compound 4+cyprodinil; C119: compound 4+iprodione; C120: compound 4+procymidone; C121: compound 4+carbendazim; C122: compound 4+thiophanate-methyl; C123: compound 4+fluindapyr; C124: compound 4+benalaxyl-M; C125: compound 4+fenpyrazamine; C125: compound 4+fluazinam; C126: compound 4+tolclofos-methyl; C127: compound 4+mandipropamid; C128: compound 4+copper oxychloride; C129: compound 4+copper salicylate; C130: compound 4+chlorothalonil; C131: compound 4+cimoxanil; C132: compound 4+dimetomorph; C133: compound 4+oxathiopiproline; C134: compound 4+fluopicolide; C135: compound 1+pyrachlostrobin; C136: compound 1+zoxamide; C137: compound 1+ametoctradin; C138: compound 1+metiram; C139: compound 1+potassium phosphite; C140: compound 1+tetraconazole+azoxystrobin, C141: compound 1+pyraclostrobin+tetraconazole; C142: compound 1+epoxyconazole+azoxystrobin; C143: compound 1+pyraclostrobin+epoxyconazole; C144: compound 1+azoxystrobin+fluindapyr; C145: compound 1+pyraclostrobin+fluindapyr; C146: compound 1+fosetyl-aluminium+copper oxychloride; C147: compound 1+fosetyl-aluminium+copper salicylate; C148: compound 1+fluindapyr+tetraconazole; C149: compound 4+tetraconazole+azoxystrobin; C150: compound 4+pyraclostrobin+tetraconazole; C151: compound 4+azoxystrobin+fluindapyr; C152: compound 4+fluindapyr+tetraconazole, C153: compound 10+tetraconazole; C154: compound 10+tebuconazole; C155: compound 10+epoxyconazole; C156: compound 10 prothioconazole; C157: compound 10+difenoconazole; C158: compound 10+penconazole; C159: compound 10+prochloraz; C160: compound 10+fenpropimorph; C161: compound 10+spiroxamine; C162: compound 10+bixafen; C163: compound 10+boscalid; C164: compound 10+carboxin; C165: compound 10+fluopyram; C166 compound 10+fluxapyroxad; C167: compound 10+isopyrazam; C168 compound 10+penthiopyrad; C169 compound 10+sedaxane; C170: compound 10+azoxystrobin; C171: compound 10+dimoxystrobin; C172: compound 10+fluoxastrobin; C173: compound 10+kresoxim-methyl; C174: compound 10+picoxystrobin; C175: compound 10+pyraclostrobin; C176: compound 10+trifloxystrobin; C177: compound 10+metrafenone; C178: compound 10+proquinazid; C179: compound 10+mepanipyrim; C180: compound 10+cyprodinil; C181: compound 10+iprodione; C182: compound 10+procymidone; C183: compound 10+carbendazim; C184: compound 10+thiophanate-methyl; C185: compound 10+fluindapyr; C186: compound 10+benalaxyl-M; C187: compound 10+fenpyrazamine; C188: compound 10+fluazinam; C189: compound 10+tolclofos-methyl; C190: compound 10+mandipropamid; C191: compound 10+copper oxychloride; C192: compound 10+copper salicylate; C193: compound 10+chlorothalonil; C194: compound 10+cimoxanil; C195: compound 10+dimetomorph; C196: compound 10+oxathiopiproline; C197: compound 10+fluopicolide; C198: compound 106+tetraconazole; C199: compound 106+tebuconazole; C200: compound 106+epoxyconazole; C201: compound 106+prothioconazole; C202: compound 106+difenoconazole; C203: compound 106+penconazole; C204: compound 106+prochloraz; C205: compound 106+fenpropimorph; C206: compound 106+spiroxamine; C208: compound 106+bixafen; C209: compound 106+boscalid; C210: compound 106+carboxin; C211: compound 106+fluopyram; C212: compound 106+fluxapyroxad; C213 compound 106+isopyrazam; C214: compound 106+penthiopyrad; C215: compound 106+sedaxane; C216: compound 106+azoxystrobin; C217: compound 106+dimoxystrobin; C218: compound 106+fluoxastrobin; C219: compound 106+kresoxim-methyl; C220: compound 106+picoxystrobin; C221: compound 106+pyraclostrobin; C222: compound 106+trifloxystrobin; C223: compound 106+metrafenone; C224: compound 106+proquinazid; C225: compound 106+mepanipyrim; C226: compound 106+cyprodinil; C227: compound 106+iprodione; C228: compound 106+procymidone; C229: compound 106+carbendazim; C230: compound 106+thiophanate-methyl; C231: compound 106+fluindapyr; C232: compound 106+benalaxyl-M; C233: compound 106+fenpyrazamine; C234: compound 106+fluazinam; C235: compound 106+tolclofos-methyl; C236: compound 106+mandipropamid; C237: compound 106+copper oxychloride; C238: compound 106+copper salicylate; C239: compound 106+chlorothalonil; C240: compound 106+cimoxanil; C241: compound 106+dimetomorph; C242: compound 106+oxathiopiproline; C243: compound 106+fluopicolide; C244: compound 107+tetraconazole; C245: compound 107+tebuconazole; C246: compound 107+epoxyconazole; C247: compound 107+prothioconazole; C248: compound 107+difenoconazole; C249: compound 107+penconazole; C250: compound 107+prochloraz; 0251: compound 107+fenpropimorph; C252: compound 107+spiroxamine; C253: compound 107+bixafen; C254: compound 107+boscalid; C255: compound 107+carboxin; C256: compound 107+fluopyram; C257: compound 107+fluxapyroxad; C258: compound 107+isopyrazam; C259: compound 107+penthiopyrad; C260: compound 107+sedaxane; C261: compound 107+azoxystrobin; C262: compound 107+dimoxystrobin; C263: compound 107+fluoxastrobin; C264: compound 107+kresoxim-methyl; C265: compound 107+picoxystrobin; C266: compound 107+pyraclostrobin; C267: compound 107+trifloxystrobin; C268: compound 107+metrafenone; C269: compound 107+proquinazid; C270: compound 107+mepanipyrim; C271: compound 107+cyprodinil; C272: compound 107+iprodione; C273: compound 107+procymidone; C274: compound 107+carbendazim; C275: compound 107+thiophanate-methyl; C276: compound 107+fluindapyr; C277: compound 107+benalaxyl-M; C278: compound 107+fenpyrazamine; C279: compound 107+fluazinam; C280: compound 107+tolclofos-methyl; C281: compound 107+mandipropamid; C282: compound 107+copper oxychloride; C283: compound 107+copper salicylate; C284: compound 107+chlorothalonil; C285: compound 107+cimoxanil; C286: compound 107+dimetomorph; C287: compound 107+oxathiopiproline; C288: compound 107+fluopicolil; C289: compound 10+tetraconazole+azoxystrobin, C290: compound 10+pyraclostrobin+tetraconazole; C291: compound 10+epoxyconazole+azoxystrobin; C292: compound 10+pyraclostrobin+epoxyconazole; C293: compound 10+azoxystrobin+fluindapyr; C294: compound 10+pyraclostrobin+fluindapyr; C295: compound 10+fosetyl-aluminium+copper oxychloride; C296: compound 10+fosetyl-aluminium+copper salicylate; C297: compound 10+fluindapyr+tetraconazole; C298: compound 106+tetraconazole+azoxystrobin, C299: compound 106+pyraclostrobin+tetraconazole; C300: compound 106+epoxyconazole+azoxystrobin; C301: compound 106+pyraclostrobin+epoxyconazole; C302: compound 106+azoxystrobin+fluindapyr; C303: compound 106+pyraclostrobin+fluindapyr; C304: compound 106+fosetyl-aluminium+copper oxychloride; C305: compound 106+fosetyl-aluminium+copper salicylate; C306: compound 106+fluindapyr+tetraconazole; C307: compound 107+tetraconazole+azoxystrobin, C308: compound 107+pyraclostrobin+tetraconazole; C309: compound 107+epoxyconazole+azoxystrobin; C310: compound 107+pyraclostrobin+epoxyconazole; C311: compound 107+azoxystrobin+fluindapyr; C312: compound 107+pyraclostrobin+fluindapyr; C313: compound 107+fosetyl-aluminium+copper oxychloride; C314: compound 107+fosetyl-aluminium+copper salicylate; C315: compound 107+fluindapyr+tetraconazole; wherein compounds 1, 2, 4, 10, 106, 107 are compounds having general formula (I) wherein the substituents have the meanings defined hereunder: TABLE-US-00010 Comp. R.sup.1 R.sup.2 R.sup.3 Y Z X n A G 1. NHCHO H O O — 0 — 2. NHCHO H O O — 0 — 4. NR.sup.2CHO H O O — 0 — 10. NHCHO H O O — 0 106. NHCHO COCH.sub.3 H O S — 0 107. NHCHO COCH.sub.3 H O S — 0

10. A method of controlling phytopathogenic fungi in agricultural crops, both curative and preventive, and for the control of phytopathogenic bacteria and viruses, comprising applying an amide according to claim 1.

11. The method according to claim 10, for the control of Plasmopara viticola on vines, Phytophtora infestans and Botrytis cinerea on tomatoes, Puccinia recondita, Erisiphae graminis, Helminthosporium teres, Septoria nodorum, Septoria tritici and Fusarium spp. on cereals, for the control of Phakopsora pachyrhizi on soybeans, for the control of Uromyces appendiculatus on beans, for the control of Venturia inaequalis on apple trees, for the control of Sphaerotheca fuliginea on cucumbers; for the control of Xanthomonas spp., Pseudomonas spp., Erwinia amylovora.

12. A method for controlling phytopathogenic fungi in agricultural crops, both curative and preventive or eradicative, for the control of fungi of the soil and for the control of phytopathogenic bacteria and viruses, comprising applying a fungicidal composition according to claim 7.

13. The method according to claim 12, for the control of Plasmopara viticola on vines, Phytophtora infestans and Botrytis cinerea on tomatoes, Phytophtora infestans on potatoes, Puccinia Recondita, Erysiphe graminis, Helminthosporium teres, Septoria spp and Fusarium spp. on cereals, for the control of Phakopsora Pachyrhizi on soybeans, for the control of Uromyces appendiculatus on beans, for the control of Venturia inaequalis on apple trees, for the control of Sphaerotheca fuliginea on cucumbers, for the control of Rhizoctonia solani, Sclerotinia spp, Pythium ultimum on horticultural plants, for the control of Xanthomonas spp., Pseudomonas spp., Erwinia amylovora.

14. A method for controlling phytopathogenic fungi in agricultural crops, which consists in applying, on any part of the plants to be protected or on the ground, effective and non-phytotoxic doses of compounds having formula (I) according to claim 1.

15. A process for preparing a compound having formula (I) according to claim 1, according to the following reaction scheme: ##STR00635## wherein a compound having formula (VII) is obtained by the reaction of a compound R.sup.2-Q with a mixture of a compound having formula (VI) dissolved in a solvent selected from the group consisting of ethyl acetate, N,N-dimethylformamide and acetone, at a temperature ranging from −15° C. to 0° C., in the presence of an organic or inorganic base, selected from the group consisting of potassium carbonate, sodium carbonate, sodium hydride, triethylamine and pyridine, optionally in the presence of a catalyst selected from the group consisting of sodium iodide, potassium iodide and a crown ether, such as 15-crown-5 or 18-crown-6, wherein, in the compound R.sup.2-Q, Q represents an outgoing group selected from the group consisting of a halogen, or a mesylate and a triflate, the other substituents having the meanings previously indicated.

16. The process for preparing a compound according to claim 15, wherein Q represents a halogen.

17. The process for preparing a compound according to claim 15, wherein Q represents an iodine atom.

Description

EXAMPLE 1

Preparation of 3-formylamino-2 hydroxy-N-(3,3,5,5-tetramethylcyclohexyl) benzamide

(1) A solution, prepared separately, obtained by dissolving 4.25 g of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide chlorohydrate (22.2 mmoles) and 3.10 ml of triethylamine (22.2 mmoles) in 100 ml of dichloromethane, was added dropwise on an ice bath, at about 0° C., to a suspension of 2.68 g of 3-formylamino salicylic acid (14.8 mmoles), 2.30 g of 3,3,5,5-tetramethylcyclohexylamine (14.8 mmol) and 3.40 g of 1-hydroxybenzotriazole (22.2 mmoles) in 100 ml of dichloromethane. After an hour, the reaction mixture was left to return to room temperature and was left under stirring at this temperature for 24 hours.

(2) After GC-MS and LC-MS control, the reaction mixture was washed with water and the phases were separated. The aqueous phase was re-extracted using dichloromethane and the organic phase was joined and washed twice with water and then with a saturated solution of sodium chloride, anhydrified on sodium sulfate, filtered and evaporated to give 5.12 g of product.

(3) The product thus obtained was purified by silica gel chromatography, eluting with heptane/ethyl acetate 9:1. 4.19 g of the desired product were obtained.

(4) Yield 88.5%.

(5) LC-MS: M.sup.+=318

EXAMPLE 2

Preparation of 3-formylamino-2-[(2-methyl-propanoyl-oxy)methoxy]-N-(3,3,5,5-tetramethylcyclohexyl)benzamide [Compound nr. 1]

(6) 4.19 g of 3-formylamino-2-hydroxy-N-(3,3,5,5-tetramethylcyclohexyl) benzamide (13.2 mmoles) dissolved in 45 ml of anhydrous N,N-dimethylformamide, were added, at −10° C., to a suspension of 0.58 g of sodium hydride (14.5 mmoles) at 60% in hexane, in 75 ml of anhydrous N,N-dimethylformamide. The reaction mixture was left at this temperature for 10 minutes, and 4.53 g of iodomethyl isobutyrate (19.80 mmoles) in 30 ml of N,N-dimethylformamide were then added dropwise and the reaction mixture was left at this temperature for about 1 hour.

(7) After GC-MS and LC-MS control, the reaction mixture was poured into water and ice, recovered with ethyl acetate, washed twice with water and then with a saturated solution of sodium chloride, anhydrified on sodium sulfate, filtered and evaporated to give 5.1 of raw product.

(8) The product thus obtained was purified by means of silica gel chromatography, eluting with heptane/ethyl acetate 9:1. 3.95 g of the desired product were obtained.

(9) Yield 71.6%

(10) LC-MS: M.sup.+=418

EXAMPLE 3

Preparation of 3-(N′-formyl-N′-[(2-methylpropanoyl-oxy)methyl]amino)-2-[(2-methylpropanoyloxy)methoxy]-N-(3,3,5,5-tetramethylcyclohexyl)-benzamide [Compound nr. 4]

(11) 4.19 g of 3-formylamino-2-hydroxy-N-(3,3,5,5-tetramethylcyclohexyl) benzamide (13.2 mmoles) dissolved in 45 ml of N,N-dimethylformamide were added at −10° C. to a suspension of 1.32 g of sodium hydride (33.0 mmoles) at 60% in hexane, in 75 ml of anhydrous N,N-dimethylformamide.

(12) The reaction mixture was left for ten minutes at this temperature, and 9.06 g of iodomethyl isobutyrate (39.60 mmoles) in 30 ml of anhydrous N,N-dimethylformamide were then added dropwise and the reaction mixture was left to return to room temperature and left under stirring for 3 hours.

(13) After GC-MS and LC-MS control, the reaction mixture was poured into water and ice, recovered with ethyl acetate, washed twice with water and then with a saturated solution of sodium chloride, anhydrified on sodium sulfate, filtered and evaporated to give 7.21 of raw product.

(14) The product thus obtained was purified by means of silica gel chromatography, eluting with heptane/ethyl acetate 9:1. 5.82 g of the desired product were obtained.

(15) Yield 85.1%

(16) LC-MS: M.sup.+=518

EXAMPLE 4

Preparation of 2-hydroxy-3-nitro-N-(3,3,5,5-tetramethylcyclohexyl)-benzamide

(17) A solution, prepared separately, obtained by dissolving 4.25 g of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide chlorohydrate (22.2 mmoles) and 3.10 ml of triethylamine (22.2 mmoles) in 100 ml of dichloromethane, was added dropwise on an ice bath, at about 0° C., to a suspension of 2.72 g of 3-nitro salicylic acid (14.8 mmoles), 2.30 g of 3,3,5,5-tetramethylcyclohexylamine (14.8 mmoles) and 3.40 g of 1-hydroxybenzotriazole (22.2 mmoles) in 100 ml of dichloromethane. After an hour, the reaction mixture was left to return to room temperature and was left under stirring at this temperature for 24 hours.

(18) After GC-MS and LC-MS control, the reaction mixture was washed with water and the phases were separated. The aqueous phase was re-extracted with dichloromethane and the organic phase was joined and washed twice with water and then with a saturated solution of sodium chloride, anhydrified on sodium sulfate, filtered and evaporated to give 4.95 g of product which was used as such for the subsequent reaction.

(19) LC-MS: M.sup.+=320

EXAMPLE 5

Preparation of 3-amino-2-hydroxy-N-(3,3,5,5-tetramethylcyclohexyl)-benzamide

(20) 0.45 g of Pd/C at 10% (0.10% w/w) were added, under a nitrogen atmosphere, to a solution of 4.95 g of 2-hydroxy-3-nitro-N-(3,3,5,5-tetramethylcyclohexyl)benzamide (14.8 mmoles theoretical) in 220 ml of ethyl acetate and the reaction mixture was hydrogenated in an autoclave at 3 bars and 30° C. for 24 hours.

(21) After GC-MS and LC-MS control, the reaction mixture was filtered on celite to eliminate the catalyst, washed twice with water and then with a saturated solution of sodium chloride, anhydrified on sodium sulfate, filtered and evaporated to give 4.02 g of raw product which was used as such for the subsequent reaction. Yield 93.6%.

(22) LC-MS: M.sup.+=290

EXAMPLE 6

Preparation of 3-(N′,N′-bis(2-methylpropanoyloxy) methyl]amino)-2-[(2-methylpropanoyloxy)methoxy]-N-(3,3,5,5-tetramethylcyclohexyl) benzamide [Compound nr. 7]

(23) 4.02 g of 3-amino-2-hydroxy-N-(3,3,5,5-tetramethylcyclohexyl)benzamide (13.8 mmoles theoretical) dissolved in 45 ml of N,N-dimethylformamide were added, at −10° C., to a suspension in 75 ml of anhydrous N,N-dimethylformamide, of 2.21 g of sodium hydride (55.20 mmoles) al 60% in hexane. The reaction mixture was left for 10 minutes at this temperature and 12.64 g of iodomethyl isobutyrate (55.20 mmoles) in 60 ml of N,N-dimethylformamide were then added dropwise and the reaction mixture was left to return to room temperature and left under stirring for 4 hours.

(24) After GC-MS and LC-MS control, the reaction mixture was poured into water and ice, recovered with ethyl acetate, washed twice with water and then with a saturated solution of sodium chloride, anhydrified on sodium sulfate, filtered and evaporated to give 9.62 g of raw product.

(25) The product thus obtained was purified by means of silica gel chromatography, eluting with heptane/ethyl acetate 9:1. 7.53 g of the desired product were obtained.

(26) Yield 92.5%.

(27) LC-MS: M.sup.+=590

EXAMPLE 7

Preparation of 3-formylamino-2-hydroxy-N-(3,3,5,5-tetramethylcyclohexyl) benzamide

(28) A suspension of 4.02 g of 3-amino-2-hydroxy-N-(3,3,5,5-tetramethylcyclohexyl)benzamide (13.8 mmoles theoretical) in 11.5 ml of formamide was stirred and heated to 150° C. for an hour.

(29) After GC-MS and LC-MS control, the reaction mixture was poured into water, extracted twice with ethyl acetate, then anhydrified on sodium sulfate, filtered and evaporated to give 4.40 g of raw product which was purified on silica gel, eluting with a mixture of heptane/ethyl acetate 6:4, obtaining 3.5 g of the desired product.

(30) Yield 80.1%

(31) LC-MS: M.sup.+=318

EXAMPLE 8

Preparation of Compounds nr. 2, 3, 5, 6, 8-107

(32) Compounds nr. 2, 3, 5, 6, 8-107 having formula (I) indicated in Table 2, were obtained by operating analogously to what is described in the previous examples.

(33) TABLE-US-00003 TABLE 2 Comp. R.sup.1 R.sup.2 R.sup.3 Y Z A X n G 1. NHCHO H O O — 0 0 2. NHCHO H O O — 0 3. NHCHO H O O — 0 4. NR.sup.2CHO H O O — 0 5. NR.sup.2CHO H O O — 0 6. NR.sup.2CHO H O O — 0 0 7. NR.sub.2.sup.2 H O O — 0 8. NR.sub.2.sup.2 H O O — 0 9. NR.sub.2.sup.2 H O O — 0 10. NHCHO H O O — 0 11. NHCHO H O O — 0 0 12. NHCHO H O O — 0 13. NHCHO H O O — 0 14. NHCHO H O O — 0 15. NHCHO H O O — 0 16. NHCHO H O O — 0 0 17. NHCHO H O O — 0 18. NHCHO H O O — 0 19. NHCHO H O O — 0 20. NHCHO CH.sub.3 O O — 0 21. NHCHO CH.sub.3 O O — 0 0 22. NHCHO CH.sub.3 O O — 0 23. NHCHO H S O — 0 24. OCH.sub.3 H S O — 0 25. NHCHO H S O — 0 26. NHCHO H O O — 0 0 27. NHCHO H O O — 0 28. NHCHO H O O — 0 29. NHCHO H O O — 0 30. NHCHO H O O — 0 31. NHCHO H O O CH.sub.2 0 0 32. NHCHO H O O CH.sub.2 0 33 OCH.sub.3 H O O — 5-Cl 1 34 OCH.sub.3 H O O — 6-Br 1 35 OCH.sub.3 H O O — 4-NO.sub.2 1 36 NHCHO H O O CH.sub.2 0 0 37 NHCHO H O O CH.sub.2 0 38 NHCHO H O O CH.sub.2 0 39 NHCHO H O O — 0 40 NHCHO H O O — 0 41 NHCHO H S O 0 00 42 NHCHO 01 H S O — 0 02 43 NHCHO 03 H O O — 0 04 44 NHCHO 05 H S O — 0 06 45 NHCHO 07 H O O — 0 08 46 NHCHO 09 H O O — 0 0 47 NHCHO H O O — 0 48 NHCHO H S O — 0 49 NHCHO H O O — 0 50 NHCHO H O O — 0 51 NHCHO H H O O — 0 52 NHCHO COCH.sub.3 H O O — 0 0 53 NHCHO H O O — 0 54 NHCHO H O O — 0 55 NHCHO H O O — 0 56 NHCHO H O O — 0 57 NHCHO H O O — 0 0 58 NHCHO H O O — 0 59 NHCHO H O O — 0 60 NHCHO H O O — 0 61 NHCHO H O O — 0 62 NHCHO H O O — 0 0 63 NHCHO H O O — 0 64 NHCHO H S O — 0 65 NHCHO H O O — 0 66 NHCHO H O O — 0 67 NHCHO H O O — 0 0 68 NHCHO H O O — 0 69 NHCHO H O O — 0 70 NHCHO H O O CH.sub.2 0 71 NHCHO H H O O — 0 72 NHCHO COCH.sub.3 H O O — 0 73 NHCHO H O O — 0 0 74 NHCHO H O O — 0 75 NHCHO H O O — 0 76 NHCHO H H O O — 0 77 NHCHO COCH.sub.3 H O O — 0 78 NHCHO H O O — 0 79 NHCHO H O O — 0 0 80 NHCHO H O O — 0 81 NHCHO H H O O — 0 82 NHCHO COCH.sub.3 H O O — 0 83 NHCHO H O O — 0 84 NHCHO H O O — 0 85 NHCHO H O O — 0 0 86 NHCHO H H O O — 0 87 NHCHO H O O — 0 88 NHCHO COCH.sub.3 H O O — 0 89 NHCHO H O O — 0 90 NHCHO H O O — 0 91 NHCHO H O S — 0 0 92 NHCHO H O S — 0 93 NHCHO H O S — 0 94. NHCHO H O S — 0 95 NHCHO H O S — 0 96 NHCHO H O S — 0 00 97 NHCHO 01 H O S — 0 02 98 NHCHO 03 H O S — 0 04 99 NHCHO 05 H O S — 0 06 100 NHCHO 07 H O S — 0 08 101 NHCHO COCH.sub.3 H O S — 0 09 102 NHCHO 0 H O S — 0 103 NHCHO COCH.sub.3 H O S — 0 104 NHCHO H O S — 0 105 NHCHO H O S — 0 106 NHCHO COCH.sub.3 H O S — 0 107 NHCHO COCH.sub.3 H O S — 0

(34) Table 3 shows the results of the GC-MS analyses on the samples 2, 3, 5, 6, 8-107.

(35) TABLE-US-00004 TABLE 3 Compound Nr. LC-MS: M+  2. 432  3. 416  5. 546  6. 514  8. 632  9. 584 10. 432 11. 446 12. 390 13. 414 14. 398 15. 482 16. 404 17. 418 18. 416 19. 418 20. 446 21. 460 22. 428 23. 430 24. 436 25. 450 26. 389 27. 338 28. 420 29. 448 30. 402 31. 546 32. 446 33  425 34. 470 35. 436 36. 448 37. 432 38. 462 39. 391 40. 405 41. 407 42. 421 43. 347 44. 363 45. 375 46. 363 47. 417 48. 433 49. 445 50. 433 51. 345 52. 387 53. 407 54. 421 55. 435 56. 435 57. 419 58. 447 59. 419 60. 447 61. 419 62. 447 63. 435 64. 449 65. 404 66. 403 67. 435 68. 473 69. 417 70. 419 71. 337 72. 379 73. 409 74. 425 75. 437 76. 353 77. 395 78. 425 79. 441 80. 453 81. 339 82. 381 83. 411 84. 427 85. 439 86. 350 87. 450 88. 392 89. 422 90. 438 91. 435 92. 449 93. 433 94. 449 95. 421 96. 433 97. 435 98. 463 99. 463 100.  451 101.  395 102.  453 103.  411 104.  469 105.  466 106.  377 107.  391

EXAMPLE 9

Determination of the Preventive Fungicidal Activity (5 Days) Against Puccinia recondita on Wheat

(36) Leaves of wheat plants of the Salgemma variety, grown in pots in a conditioned environment at 20° C. and 70% of Relative Humidity (RH) were treated by spraying both sides of the leaves with the compound under examination (see Table 4 hereunder) dispersed in a hydroacetone solution at 20% by volume of acetone.

(37) After remaining 5 days in a conditioned environment, the plants were sprayed on both sides of the leaves with an aqueous suspension of conidia of Puccinia recondita (2 mg of inoculum per 1 ml of solution for infection).

(38) After spraying, the plants were kept in a humidity-saturated environment at a temperature ranging from 18 to 24° C. for the incubation period of the fungus (1 day).

(39) At the end of this period, the plants were put in a greenhouse with a relative humidity (RH) of 70% and at a temperature of 18-24° C. for 14 days.

(40) At the end of this period, the external symptoms of the pathogen appeared and it was therefore possible to proceed with the visual evaluation of the intensity of the infection, both on the parts treated directly with the products (T) and on the parts developed during the implementation of the test (NT).

(41) The fungicidal activity is expressed as a percentage of the reduction, with respect to non-treated seedlings (comparison), in the area of the leaf affected by the disease (100=full effectiveness; 0=zero effectiveness).

(42) All of the compounds 1, 2, 3, 5 showed full activity (100%) at the dosage of 250 ppm. At the same time, an evaluation of the phytotoxicity was effected (percentage of leaf necrosis) induced on the wheat seedlings by the application of the products: in this case the evaluation scale ranges from 0 (completely healthy plant) to 100 (completely necrotic plant).

(43) Table 4 indicates the results obtained by carrying out the test described with compounds 1, 2, and 4 compared with compound 504 described in WO9927783: CR1: 3-formylamino-2-hydroxy-N-(3,3,5,5-tetramethylcyclohexyl)benzamide

(44) TABLE-US-00005 TABLE 4 P5 activity Compound Nr. ppm T NT 1 125 70 60 250 75 65 2 125 60 55 250 70 65 4 125 70 65 250 80 70 CR1 125 50 35 250 65 50

EXAMPLE 10

Determination of the Preventive Activity (7 Days) of the Compounds Having Formula (I) Against Plasmopara viticola on Vines

(45) Leaves of vine plants of the Merlot variety, grown in pots, in a conditioned environment, (20±1° C., 70% of R.H.) were treated by spraying both sides with the compound under examination.

(46) 7 days after the treatment, the plants were inoculated with an aqueous suspension of spores of Plasmopara viticola (200,000 spores/cc) by spraying both sides of the leaves with a compressed air gun.

(47) After remaining 24 hours in a humidity-saturated environment, at 21° C. the plants were transferred for an incubation period (7 days) in a conditioned environment at 70% of R H. and at 24° C.

(48) At the end of this period, the external symptoms of the pathogen appeared and it was therefore possible to proceed with the evaluation of the intensity of the infection.

(49) The fungicidal activity was expressed as the reduction percentage, with respect to non-treated seedlings, in the area of the leaf affected by the disease (100=full effectiveness; 0=zero effectiveness).

(50) Table 5 indicates the results obtained by carrying out the test described with compounds nr. 1, 2 and 4 compared with compound 504 described in WO9927783. CR1: 3-formylamino-2-hydroxy-N-(3,3,5,5-tetramethylcyclohexyl)benzamide

(51) TABLE-US-00006 TABLE 5 Compound Nr ppm P7 activity 1 30 100 125 100 2 30 95 125 100 4 30 100 125 100 CR1 30 50 125 65

EXAMPLE 11

Determination of the Fungicidal Activity of the Compounds Having Formula (I) Against Helmintosporium Teres on Barley

(52) Leaves of barley plants (cultivar Gemini), grown in pots in a conditioned environment (20±1° C., 70% of R.H.), were treated by spraying both sides of the leaves with the compounds under examination, dispersed in a hydro-acetate solution at 20% by volume of acetone.

(53) After remaining 5 days in a conditioned environment, the plants were sprayed on both sides of the leaves with an aqueous suspension of conidia of Helmintosporium teres (50,000 conidia per cm.sup.3 (adding Tween 20-1 drop/100 ml).

(54) The plants were then kept in a controlled environment during the incubation period of the fungus (1 day wet room for infection, 3 days in a cell with R.H. 70% and 0° C. for the incubation period, 3 days for wet room evasion, 12 days biological cycle).

(55) At the end of this period (12 days), the fungicidal activity was evaluated according to an evaluation percentage scale from 0 (plant completely infected) to 100 (healthy plant).

(56) Table 6 indicates the results obtained by carrying out the test described with compound nr. 1 compared with compound 504 described in WO9927783. CR1: 3-formylamino-2-hydroxy-N-(3,3,5,5-tetramethylcyclohexyl)benzamide

(57) TABLE-US-00007 TABLE 6 Compound Nr ppm P7 activity 1 125 75 250 80 CR1 125 5 250 15