4-Aminoquinazoline compounds useful as agricultural fungicides

Abstract

Agricultural fungicidal compositions containing as an active ingredient one or more 4-aminoquinazoline derivatives. The amino group is substituted, e.g., with a phenoxyalkylene, and the quinazoline nucleus may be substituted at 2- and or 6-positions.

Description

The invention relates to agricultural fungicidal compositions containing as an active ingredient one or more 4-aminoquinazoline derivatives.

More particularly, it relates to agricultural fungicidal compositions containing as an active ingredient one or more 4-aminoquinazoline derivatives represented by formula (I): ##STR1## in which:

A and B are the same or different and each represents a hydrogen atom, a lower alkyl group, a halogen atom or a nitro group;

X represents an alkylene group;

Y represents an oxygen atom or a sulfur atom;

Z represents an alkyl group, an aralkyl group;

a naphthyl group, an unsubstituted phenyl group or a phenyl group substituted with 1 to 3 substituents which are the same or different and are selected from the group consisting of a lower alkyl group, an alkoxy group, an alkylthio group, a phenyl group, a trifluoromethyl group and a halogen atom; or salts thereof.

A class of 4-aminoquinazoline derivatives is disclosed in Japanese Patent Publication Specification No. 43-29033, which corresponds to U.S. Pat. No. 3,541,094 as being effective controlling agents against phytopathogenic fungi.

The inventors have found that the compounds of formula (I) show a broad and superior fungicidal activity than the known compounds mentioned above against bacteria and fungi parasitic on agricultural and horticultural plants. More specifically, the compounds of formula (I) show a remarkable controlling effect against, for example, blast, brown spot, sheath blight and bacterial leaf blight of rice plants; late blight and early blight of tomatoes; and anthracnose, downy mildew and powdery mildew of cucumbers. They also show a controlling effect against phytoparasitic soil fungi, as well as algal fungi which adversely affect the germination of rice plants.

Further, some of the compounds of formula (I) show a strong inhibiting activity of ingestion against the fourth to final instar larvae of Lepidoptera such as cabbage armyworm and tobacco cutworm, and therefore are useful as an insect repellent. Furthermore, some of the compounds of formula (I) may be used as an insecticidal and acaricidal agent gainst, e.g., two-spotted spider mite.

In the compounds of formula (I), when A and/or B each represents a lower alkyl group, it may be a straight or branched chain alkyl having 1 to 4 carbon atoms, for example, a methyl, ethyl, n-propyl, isopropyl, n-butyl or sec-butyl, preferably a methyl.

When A and/or B each represents a halogen atom, it may be, for example, a chlorine, bromine, fluorine or iodine, preferably a chlorine.

X is a straight or branched alkylene and it may be, for example, a methylene, ethylene, methylmethylene, trimethylene, ethylmethylene, dimethylmethylene, propylene, tetramethylene, 1,1-dimethylethylene, 1,2-dimethylethylene, 2,2-dimethylethylene, 1-ethylethylene, 2-ethylethylene, pentamethylene, hexamethylene, heptamethylene, octamethylene, 2-ethylhexamethylene, 5-ethylhexamethylene, decamethylene, dodecamethylene, hexadecamethylene or octadecamethylene; and it is preferably a straight or branched chain alkylene having 2 to 8 carbon atoms.

When Z is an alkyl group, it may be, for example a methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-amyl, isoamyl, sec-amyl, n-heptyl, n-octyl, 2-ethylhexyl, decyl, dodecyl, tetradecyl, hexadecyl or octadecyl; and it is preferably a straight or branched alkyl having 1 to 8 carbon atoms.

When Z is a naphthyl group, it may be a 1-naphthyl or 2-naphthyl.

When Z is an aralkyl group, it may be, for example, a benzyl, .alpha.-methylbenzyl or phenethyl, preferably a benzyl.

When Z is a phenyl group substituted with lower alkyl, the lower alkyl may be straight or branched chain alkyl having 1 to 4 carbon atoms such as methyl, ethyl, n-propyl isopropyl, n-butyl or sec-butyl, preferably methyl.

When Z is a phenyl group substituted with lower alkoxy, the lower alkoxy may be straight or branched chain alkoxy having 1 to 4 carbon atoms such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy or isobutoxy, preferably methoxy or ethoxy.

When Z is a phenyl group substituted with lower alkylthio, the lower alkylthio may be straight or branched chain alkylthio having 1 to 4 carbon atoms such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio or isobutylthio, preferably methyl thio.

When Z is a phenyl group substituted with halogen atom, the halogen atom may be chlorine, bromine, fluorine or iodine, preferably chlorine.

Of the compounds of formula (I), the preferable class of compounds is when A is a hydrogen atom or a chlorine atom; B is a hydrogen atom, a methyl group, a chlorine atom or a nitro group; X is a straight or branched alkylene group having from 2 to 8 carbon atoms; and Z is an unsubstituted phenyl group or a phenyl group substituted with 1 to 3 substituents which are the same or different and are selected from the group consisting of a methyl, methoxy, ethoxy, methylthio, trifluoromethyl and chlorine.

Among the preferable compounds mentioned above, the more preferable class of compounds is when both A and B are hydrogen atoms; X is a straight or branched chain alkylene group having 2 to 8 carbon atoms; and Z is an unsubstituted phenyl group or a phenyl group substituted with a methyl, methoxy, ethoxy or chlorine.

The most preferable class of compounds is when both A and B are hydrogen atoms; X is a straight or branched alkylene group having 2 to 8 carbon atoms; Y is an oxygen atom; and Z is an unsubstituted phenyl group or a phenyl group substituted with a methyl, methoxy, ethoxy or chlorine.

As can be understood by formula (I), the compounds of the invention have at least one asymmetric carbon atom, depending on the species of the alkylene group X. In such cases, there can be present various different optical isomers. It is, therefore, to be understood that the individual stereoisomers as well as physical or racemic mixtures thereof are included within the scope of the invention.

The compounds of formula (I) may readily form acid addition salts; and such salts may also be used as the active ingredient of the agricultural fungicides of the invention.

Acids to form addition salts include: inorganic acids such as hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid and phosphoric acid; carboxylic acids such as formic acid, oxalic acid and trichloroacetic acid; and organic sulfonic acids such as methanesulfonic acid, benzenesulfonic acid and toluenesulfonic acid. Thereof, hydrochloric acid is preferable.

Further, the compounds of formula (I) may form hydrates with water; and the hydrates may also be used as the active ingredient of the agricultural fungicides of the invention.

The compounds of formula (I) used as the active ingredient of the fungicides of the invention will be illustrated below. The numbers appended to the compounds will be used to identify them hereafter.

1. 4-(2-Methoxyethyl)aminoquinazoline 2. 4-(2-Ethoxyethyl)aminoquinazoline 3. 4-(2-Ethylthioethyl)aminoquinazoline 4. 2-Chloro-4-(2-ethoxyethyl)aminoquinazoline 5. 2-Chloro-4-(2-ethylthioethyl)aminoquinazoline 6. 6-Chloro-4-(2-ethoxyethyl)aminoquinazoline 7. 4-(2-n-Propylthioethyl)aminoquinazoline 8. 4-(2-Phenoxyethyl)aminoquinazoline 9. 4-(2-Phenylthioethyl)aminoquinazoline 10. 2-Chloro-4-(2-phenoxyethyl)aminoquinazoline 11. 2-Chloro-4-(2-phenylthioethyl)aminoquinazoline 12. 6-Chloro-4-(2-phenoxyethyl)aminoquinazoline 13. 6-Methyl-4-(2-phenoxyethyl)aminoquinazoline 14. 4-[2-(2-Chlorophenoxy)ethyl]aminoquinazoline 15. 4-[2-(2-Bromophenoxy)ethyl]aminoquinazoline 16. 4-[2-(2-Iodophenoxy)ethyl]aminoquinazoline 17. 4-[2-(2-Fluorophenoxy)ethyl]aminoquinazoline 18. 2-Chloro-4-[2-(2-chlorophenoxy)ethyl]aminoquinazoline 19. 6-Chloro-4-[2-(2-chlorophenoxy)ethyl]aminoquinazoline 20. 4-[2-(2-Methylphenoxy)ethyl]aminoquinazoline 21. 4-[2-(2-Methylphenylthio)ethyl]aminoquinazoline 22. 2-Chloro-4-[2-(2-methylphenoxy)ethyl]aminoquinazoline 23. 6-Chloro-4-[2-(2-methylphenoxy)ethyl]aminoquinazoline 24. 6-Methyl-4-[2-(2-methylphenoxy)ethyl]aminoquinazoline 25. 6-Isopropyl-4-[2-(2-methylphenoxy)ethyl]aminoquinazoline 26. 2-Chloro-4-[2-(2-methylphenylthio)ethyl]aminoquinazoline 27. 4-[2-(2-Ethylphenoxy)ethyl]aminoquinazoline 28. 4-[2-(2-Isopropylphenoxy)ethyl]aminoquinazoline 29. 4-[2-(2-sec-Butylphenoxy)ethyl]aminoquinazoline 30. 4-[2-(2-Methoxyphenoxy)ethyl]aminoquinazoline 31. 6-Methyl-4-[2-(2-methoxyphenoxy)ethyl]aminoquinazoline 32. 4-[2-(2-Ethoxyphenoxy)ethyl]aminoquinazoline 33. 6-Chloro-4-[2-(2-ethoxyphenoxy)ethyl]aminoquinazoline 34. 4-[2-(2-n-Butoxyphenoxy)ethyl]aminoquinazoline 35. 4-[2-(o-Phenylphenoxy)ethyl]aminoquinazoline 36. 4-[2-(p-Phenylphenoxy)ethyl]aminoquinazoline 37. 6-Chloro-4-[2-(o-phenylphenoxy)ethyl]aminoquinazoline 38. 4-[2-(2-Trifluoromethylphenoxy)ethyl]aminoquinazoline 39. 4-[2-(3-Chlorophenoxy)ethyl]aminoquinazoline 40. 6-Methyl-4-[2-(3-chlorophenoxy)ethyl]aminoquinazoline 41. 4-[2-(3-Methylphenoxy)ethyl]aminoquinazoline 42. 4-[2-(3-Methylphenylthio)ethyl]aminoquinazoline 43. 2-Chloro-4-[2-(3-methylphenoxy)ethyl]aminoquinazoline 44. 2-Chloro-4-[2-(3-methylphenylthio)ethyl]aminoquinazoline 45. 4-[2-(3-Trifluoromethylphenoxy)ethyl]aminoquinazoline 46. 4-[2-(4-Chlorophenoxy)ethyl]aminoquinazoline 47. 4-[2-(4-Chlorophenylthio)ethyl]aminoquinazoline 48. 4-[2-(4-Bromophenoxy)ethyl]aminoquinazoline 49. 4-[2-(4-Bromophenylthio)ethyl]aminoquinazoline 50. 4-[2-(4-Fluorophenoxy)ethyl]aminoquinazoline 51. 4-[2-(4-Methylphenoxy)ethyl]aminoquinazoline 52. 4-[2-(4-Methylphenylthio)ethyl]aminoquinazoline 53. 2-Chloro-4-[2-(4-methylphenoxy)ethyl]aminoquinazoline 54. 2-Chloro-4-[2-(4-Methylphenylthio)ethyl]aminoquinazoline 55. 6-Methyl-4-[2-(4-methylphenoxy)ethyl]aminoquinazoline 56. 4-[2-(4-tert-Butylphenoxy)ethyl]aminoquinazoline 57. 4-[2-(4-Methoxyphenoxy)ethyl]aminoquinazoline 58. 4-[2-(4-Isopropoxyphenoxy)ethyl]aminoquinazoline 59. 4-[2-(2,4-Dichlorophenoxy)ethyl]aminoquinazoline 60. 4-[2-(2,4-Dibromophenoxy)ethyl]aminoquinazoline 61. 6-Chloro-4-[2-(2,4-dichlorophenoxy)ethyl]aminoquinazoline 62. 4-[2-(2-Methyl-4-chlorophenoxy)ethyl]aminoquinazoline 63. 2-Chloro-4-[2-(2-methyl-4-chlorophenoxy)ethyl]aminoquinazoline 64. 4-[2-(2,4-Dimethylphenoxy)ethyl]aminoquinazoline 65. 4-[2-(2-Chloro-4-methoxyphenoxy)ethyl]aminoquinazoline 66. 4-[2-(2-Bromo-4-isopropylphenoxy)ethyl]aminoquinazoline 67. 6-Chloro-4-[2-(2,5-dimethylphenoxy)ethyl]aminoquinazoline 68. 4-[2-(2,6-Dimethylphenoxy)ethyl]aminoquinazoline 69. 4-[2-(2,6-Diethylphenoxy)ethyl]aminoquinazoline 70. 2-Chloro-4-[2-(2,6-dimethylphenoxy)ethyl]aminoquinazoline 71. 4-[2-(3-Methyl-4-methylthiophenoxy)ethyl]aminoquinazoline 72. 6-Bromo-[2-(3-methyl-4-n-butylthiophenylthio)ethyl]aminoquinazoline 73. 4-[2-(3,5-Dimethylphenoxy)ethyl]aminoquinazoline 74. 2-Chloro-4-[2-(3,5-dimethylphenoxy)ethyl]aminoquinazoline 75. 6-Chloro-4-[2-(3,5-dimethylphenoxy)ethyl]aminoquinazoline 76. 4-[2-(2,4,5-Trichlorophenoxy)ethyl]aminoquinazoline 77. 4-[2-(2,4,6-Tribromophenoxy)ethyl]aminoquinazoline 78. 6-Chloro-4-[2-(2,4,5-trichlorophenoxy)ethyl]aminoquinazoline 79. 4-[2-(2,4,6-Trichlorophenoxy)ethyl]aminoquinazoline 80. 4-[2-(2,4,6-Triiodophenoxy)ethyl]aminoquinazoline 81. 6-Chloro-4-[2-(2,4,6-trichlorophenoxy)ethyl]aminoquinazoline 82. 4-[2-(2,3,6-Trimethylphenoxy)ethyl]aminoquinazoline 83. 6-Bromo-4-[2-(2,6-dichloro-4-bromophenoxy)ethyl]aminoquinazoline 84. 4-[2-(1-Naphthoxy)ethyl]aminoquinazoline 85. 6-Chloro-4-[2-(1-naphthoxy)ethyl]aminoquinazoline 86. 4-[2-(Benzyloxy)ethyl]aminoquinazoline 87. 4-[2-Benzylthio)ethyl]aminoquinazoline 88. 2-Chloro-4-[2-(benzylthio)ethyl]aminoquinazoline 89. 4-[2-(Phenethyloxy)ethyl]aminoquinazoline 90. 4-[2-(.alpha.-Methylbenzyloxy)ethyl]aminoquinazoline 91. 4-(3-Methoxypropyl)aminoquinazoline 92. 4-(3-Ethoxypropyl)aminoquinazoline 93. 2-Chloro-4-(3-ethoxypropyl)aminoquinazoline 94. 6-Nitro-4-(3-ethoxypropyl)aminoquinazoline 95. 4-(3-Isopropoxypropyl)aminoquinazoline 96. 4-(3-n-Butoxypropyl)aminoquinazoline 97. 2-Chloro-4-(3-n-butoxypropyl)aminoquinazoline 98. 4-[3-(2-Ethylhexyloxy)propyl]aminoquinazoline 99. 6-Nitro-4-[3-(2-ethylhexyloxy)propyl]aminoquinazoline 100. 4-(3-Dodecyloxypropyl)aminoquinazoline 101. 6-Iodo-4-(3-stearyloxypropyl)aminoquinazoline 102. 4-(3-Phenoxypropyl)aminoquinazoline 103. 4-(3-Phenylthiopropyl)aminoquinazoline 104. 2-Chloro-4-(3-phenoxypropyl)aminoquinazoline 105. 2-Chloro-4-(3-phenylthiopropyl)aminoquinazoline 106. 6-Methyl-4-(3-phenoxypropyl)aminoquinazoline 107. 6-Methyl-4-(3-phenylthiopropyl)aminoquinazoline 108. 6-Nitro-4-(3-phenoxypropyl)aminoquinazoline 109. 4-[3-(2-Chlorophenoxy)propyl]aminoquinazoline 110. 4-[3-(2-Methylphenoxy)propyl]aminoquinazoline 111. 4-[3-(2-Methylphenylthio)propyl]aminoquinazoline 112. 4-[3-(2-Methoxyphenoxy)propyl]aminoquinazoline 113. 4-[3-(3-Chlorophenoxy)propyl]aminoquinazoline 114. 4-[3-(3-Methylphenoxy)propyl]aminoquinazoline 115. 4-[3-(3-Methylphenylthio)propyl]aminoquinazoline 116. 2-Chloro-4-[3-(3-methylphenoxy)propyl]aminoquinazoline 117. 2-Chloro-4-[3-(3-methylphenylthio)propyl]aminoquinazoline 118. 4-[3-(4-Chlorophenoxy)propyl]aminoquinazoline 119. 2-Chloro-4-[3-(4-chlorophenoxy)propyl]aminoquinazoline 120. 4-[3-(4-Methylphenoxy)propyl]aminoquinazoline 121. 4-[3-(4-Methylphenylthio)propyl]aminoquinazoline 122. 2-Chloro-4-[3-(4-methylphenylthio)propyl]aminoquinazoline 123. 6-Iodo-4-[3-(4-tert-butylphenoxy)propyl]aminoquinazoline 124. 4-[3-(4-methoxyphenoxy)propyl]aminoquinazoline 125. 4-[3-(2,5-Dimethylphenoxy)propyl]aminoquinazoline 126. 4-[3-(2-Methyl-4-chlorophenoxy)propyl]aminoquinazoline 127. 4-[3-(2-Chloro-4-methoxyphenoxy)propyl]aminoquinazoline 128. 4-[3-(3-Methyl-4-chlorophenoxy)propyl]aminoquinazoline 129. 4-[3-(3,5-Dimethylphenoxy)propyl]aminoquinazoline 130. 6-Chloro-4-[3-(2,4,6-trimethylphenoxy)propyl]aminoquinazoline 131. 4-[3-(1-Naphthoxy)propyl]aminoquinazoline 132. 2-Chloro-4-[3-(2-naphthylthio)propyl]aminoquinazoline 133. 4-(1-Methyl-2-methoxyethyl)aminoquinazoline 134. 4-(1-Methyl-2-octyloxyethyl)aminoquinazoline 135. 4-(1-Methyl-2-phenoxyethyl)aminoquinazoline 136. 2-Chloro-4-(1-methyl-2-phenoxyethyl)aminoquinazoline 137. 6-Methyl-4-(1-methyl-2-phenoxyethyl)aminoquinazoline 138. 6-Bromo-4-(1-methyl-2-phenylthioethyl)aminoquinazoline 139. 4-[1-Methyl-2-(2-methylphenoxy)ethyl]aminoquinazoline 140. 4-[1-Methyl-2-(2-methoxyphenoxy)ethyl]aminoquinazoline 141. 4-[1-Methyl-2-(3-chlorophenoxy)ethyl]aminoquinazoline 142. 4-[1-Methyl-2-(3-methylphenoxy)ethyl]aminoquinazoline 143. 4-[1-Methyl-2-(3-isopropylphenylthio)ethyl]aminoquinazoline 144. 4-[1-Methyl-2-(4-chlorophenoxy)ethyl]aminoquinazoline 145. 2-Chloro-4-[1-methyl-2-(4-chlorophenoxy)ethyl]aminoquinazoline 146. 6-Bromo-4-[1-methyl-2-(4-iodophenylthio)ethyl]aminoquinazoline 147. 4-[1-Methyl-2-(4-methylphenoxy)ethyl]aminoquinazoline 148. 2-Chloro-4-[1-methyl-2-(4-methylphenoxy)ethyl]aminoquinazoline 149. 4-[1-Methyl-2-(4-n-butoxyphenoxy)ethyl]aminoquinazoline 150. 4-[1-Methyl-2-(4-phenylphenoxy)ethyl]aminoquinazoline 151. 4-(2-Methyl-2-phenoxyethyl)aminoquinazoline 152. 2-Chloro-4-(2-methyl-2-phenoxyethyl)aminoquinazoline 153. 4-[2-Methyl-2-(2-chlorophenoxy)ethyl]aminoquinazoline 154. 4-[2-Methyl-2-(2-methylphenoxy)ethyl]aminoquinazoline 155. 2-Chloro-4-[2-methyl-2-(2-methylphenoxy)ethyl]aminoquinazoline 156. 6-Chloro-4-[2-methyl-2-(2-tert-butylphenoxy)ethyl]aminoquinazoline 157. 4-[2-Methyl-2-(2-methoxyphenoxy)ethyl]aminoquinazoline 158. 4-[2-Methyl-2-(3-chlorophenoxy)ethyl]aminoquinazoline 159. 4-[2-Methyl-2-(3-methylphenoxy)ethyl]aminoquinazoline 160. 4-[2-Methyl-2-(4-chlorophenoxy)ethyl]aminoquinazoline 161. 4-[2-Methyl-2-(4-bromophenoxy)ethyl]aminoquinazoline 162. 2-Chloro-4-[2-methyl-2-(4-chlorophenoxy)ethyl]aminoquinazoline 163. 4-[2-Methyl-2-(4-methylphenoxy)ethyl]aminoquinazoline 164. 2-Chloro-4-[2-methyl-2-(4-methylphenoxy)ethyl]aminoquinazoline 165. 4-[2-Methyl-2-(4-phenylphenoxy)ethyl]aminoquinazoline 166. 6-Methyl-4-[2-methyl-2-(4-n-butylthiophenoxy)ethyl]aminoquinazoline 167. 4-(4-Ethoxybutyl)aminoquinazoline 168. 4-(4-Dodecylthiobutyl)aminoquinazoline 169. 4-(4-Benzyloxybutyl)aminoquinazoline 170. 4-(4-Phenoxybutyl)aminoquinazoline 171. 6-Methyl-4-(4-phenoxybutyl)aminoquinazoline 172. 4-[4-(2-Chlorophenoxy)butyl]aminoquinazoline 173. 4-[4-(2-Methylphenoxy)butyl]aminoquinazoline 174. 4-[4-(2-Methoxyphenoxy)butyl]aminoquinazoline 175. 4-[4-(3-Methylphenoxy)butyl]aminoquinazoline 176. 4-[4-(3-Chlorophenoxy)butyl]aminoquinazoline 177. 6-Bromo-4-[4-(3-bromophenylthio)butyl]aminoquinazoline 178. 4-[4-(3-Phenylphenoxy)butyl]aminoquinazoline 179. 4-[4-(4-Methylphenoxy)butyl]aminoquinazoline 180. 4-[4-(4-Isopropylphenoxy)butyl]aminoquinazoline 181. 4-[4-(4-Methylthiophenylthio)butyl]aminoquinazoline 182. 4-(2-Ethyl-2-benzyloxyethyl)aminoquinazoline 183. 4-(2-Ethyl-2-phenoxyethyl)aminoquinazoline 184. 4-[2-Ethyl-2-(2-methoxyphenoxy)ethyl]aminoquinazoline 185. 2-Chloro-4-[2-ethyl-2-(4-chlorophenoxy)ethyl]aminoquinazoline 186. 4-(1-Ethyl-2-methoxyethyl)aminoquinazoline 187. 6-Bromo-4-(1-ethyl-2-benzyloxyethyl)aminoquinazoline 2-Chloro-4-(1-ethyl-2-phenoxyethyl)aminoquinazoline 4-[1-Ethyl-2-(2-chlorophenoxy)ethyl]aminoquinazoline 4-[1-Ethyl-2-(3-methylphenoxy)ethyl]aminoquinazoline 4-[1-Ethyl-2-(4-isopropoxyphenylthio)ethyl]aminoquinazoline 4-(2,2-Dimethyl-2-ethoxyethyl)aminoquinazoline 2-Chloro-4-(2,2-dimethyl-2-octyloxyethyl)aminoquinazoline 6-Methyl-4-(2,2-dimethyl-2-benzylthioethyl)aminoquinazoline 4-(2,2-Dimethyl-2-phenoxyethyl)aminoquinazoline 2-Chloro-4-(2,2-dimethyl-2-phenoxyethyl)aminoquinazoline 4-[2,2-Dimethyl-2-(2-chlorophenoxy)ethyl]aminoquinazoline 4-[2,2-Dimethyl-2-(2-methylphenoxy)ethyl]aminoquinazoline 2-Chloro-4-[2,2-dimethyl-2-(2-methylphenoxy)ethyl]aminoquinazoline 4-[2,2-Dimethyl-2-(2-methoxyphenoxy)thyl]aminoquinazoline 4-[2,2-Dimethyl-2-(3-chlorophenoxy)ethyl]aminoquinazoline 4-[2,2-Dimethyl-2-(3-methylphenoxy)ethyl]aminoquinazoline 2-Chloro-4-[2,2-dimethyl-2-(3-methylphenoxy)ethyl]aminoquinazoline 4-[2,2-Dimethyl-2-(4-chlorophenoxy)ethyl]aminoquinazoline 4-[2,2-Dimethyl-2-(4-bromophenoxy)ethyl]aminoquinazoline 4-[2,2-Dimethyl-2-(4-methylphenoxy)ethyl]aminoquinazoline 4-[2,2-Dimethyl-2-(4-isopropylphenylthio)ethyl]aminoquinazoline 2-Chloro-4-[2,2-dimethyl-2-(4-methylphenoxy)ethyl]aminoquinazoline 4-(1,1-Dimethyl-2-phenoxyethyl)aminoquinazoline 4-[1,1-Dimethyl-2-(2-methylphenoxy)ethyl]aminoquinazoline 4-[1,1-Dimethyl-2-(3-methoxyphenoxy)ethyl]aminoquinazoline 4-(1,2-Dimethyl-2-dodecyloxyethyl)aminoquinazoline 4-(1,2-Dimethyl-2-phenoxyethyl)aminoquinazoline 4-[1,2-Dimethyl-2-(2-chlorophenoxy)ethyl]aminoquinazoline 4-[1,2-Dimethyl-2-(3-methylphenoxy)ethyl]aminoquinazoline 2-Chloro-4-[1,2-dimethyl-2-(4-methoxyphenylthio)ethyl]aminoquinazoline 4-(5-n-Butoxypentyl)aminoquinazoline 4-(5-Octoxypentyl)aminoquinazoline 4-[5-(2-Ethylhexyloxy)pentyl]aminoquinazoline 4-(5-Stearyloxypentyl)aminoquinazoline 4-(5-Benzylthiopentyl)aminoquinazoline 4-(5-Phenoxypentyl)aminoquinazoline 4-[5-(2-Chlorophenoxy)pentyl]aminoquinazoline 2-Chloro-4-[5-(2-chlorophenoxy)pentyl]aminoquinazoline 4-[5-(2-Methylphenoxy)pentyl]aminoquinazoline 4-[5-(2-Methoxyphenoxy)pentyl]aminoquinazoline 2-Chloro-4-[5-(2-methoxyphenylthio)pentyl]aminoquinazoline 4-[5-(3-Chlorophenoxy)pentyl]aminoquinazoline 4-[5-(3-Methylphenoxy)pentyl]aminoquinazoline 4-[5-(3-Methoxyphenoxy)pentyl]aminoquinazoline 4-[5-(4-Chlorophenoxy)pentyl]aminoquinazoline 4-[5-(4-Methylphenoxy)pentyl]aminoquinazoline 4-[5-(4-Methoxyphenoxy)pentyl]aminoquinazoline 4-(6-Phenoxyhexyl)aminoquinazoline 4-[6-(2-Chlorophenoxy)hexyl]aminoquinazoline 4-[6-(2-Methylphenoxy)hexyl]aminoquinazoline 6-Chloro-4-[6-(2-methylphenoxy)hexyl]aminoquinazoline 4-[6-(3-Chlorophenoxy)hexyl]aminoquinazoline 4-[6-(3-Methylphenoxy)hexyl]aminoquinazoline 4-[6-(3-Methoxyphenoxy)hexyl]aminoquinazoline 4-[6-(4-Chlorophenoxy)hexyl]aminoquinazoline 4-[6-(4-Chlorophenylthio)hexyl]aminoquinazoline 4-[6-(4-Methylphenoxy)hexyl]aminoquinazoline 4-[6-(4-Methoxyphenoxy)hexyl]aminoquinazoline 2-Chloro-4-[6-(4-methoxyphenoxy)hexyl]aminoquinazoline 4-(7-Isopropoxyheptyl)aminoquinazoline 4-(7-Dodecylthioheptyl)aminoquinazoline 4-(7-Phenoxyheptyl)aminoquinazoline 4-[7-(2-Chlorophenoxy)heptyl]aminoquinazoline 4-[7-(2-Methylphenoxy)heptyl]aminoquinazoline 4-[7-(2-Methoxyphenoxy)heptyl]aminoquinazoline 4-[7-(3-Chlorophenoxy)heptyl]aminoquinazoline 4-[7-(3-Methylphenoxy)heptyl]aminoquinazoline 4-[7-(4-Chlorophenoxy)heptyl]aminoquinazoline 4-[7-(4-Methylphenoxy)heptyl]aminoquinazoline 4-[7-(4-Methoxyphenoxy)heptyl]aminoquinazoline 4-[7-(2,4-Dichlorophenoxy)heptyl]aminoquinazoline 4-[7-(3,5-Dimethylphenoxy)heptyl]aminoquinazoline 4-(8-Methoxyoctyl)aminoquinazoline 4-(8-Benzylthiooctyl)aminoquinazoline 4-(8-Phenoxyoctyl)aminoquinazoline 4-[8-(2-Chlorophenoxy)octyl]aminoquinazoline 4-[8-(2-Methylphenoxy)octyl]aminoquinazoline 4-[8-(2-Methoxyphenoxy)octyl]aminoquinazoline 4-[8-(3-Chlorophenoxy)octyl]aminoquinazoline 4-[8-(3-Methylphenyl)octyl]aminoquinazoline 4-[8-(3-Methoxyphenyl)octyl]aminoquinazoline 4-[8-(4-Chlorophenoxy)octyl]aminoquinazoline 4-[8-(4-Methylphenoxy)octyl]aminoquinazoline 4-[8-(4-Methylthiophenoxy)octyl]aminoquinazoline 4-[8-(4-Methoxyphenoxy)octyl]aminoquinazoline 4-[8-(3,5-Dichlorophenoxy)octyl]aminoquinazoline 4-[8-(2,6-Dimethylphenoxy)octyl]aminoquinazoline 4-(10-Methoxydecyl)aminoquinazoline 4-(10-Phenoxydecyl)aminoquinazoline 4-[10-(2-Chlorophenoxy)decyl]aminoquinazoline 4-[10-(3-Methylphenoxy)decyl]aminoquinazoline 4-[10-(4-Methoxyphenoxy)decyl]aminoquinazoline 4-(12-Phenoxydodecyl)aminoquinazoline 4-[12-(2-Methylphenoxy)dodecyl]aminoquinazoline 4-[12-(3-Chlorophenoxy)dodecyl]aminoquinazoline 4-[12-(4-Methoxyphenoxy)dodecyl]aminoquinazoline 4-(16-Phenoxyhexadecyl)aminoquinazoline 4-(18-Phenoxyoctadecyl)aminoquinazoline 4-[2-(2-n-Propylphenoxy)ethyl]aminoquinazoline 6-Methyl-4-[4-(2-chlorophenoxy)butyl]aminoquinazoline 4-[2-(2-Methoxy-4-methylphenoxy)ethyl]aminoquinazoline 4-[2-(3-Methoxyphenoxy)ethyl]aminoquinazoline 4-[2-(2-Methoxy-4-chlorophenoxy)ethyl]aminoquinazoline 4-[2-(2-Methyl-3-chlorophenoxy)ethyl]aminoquinazoline 2-Methyl-4-(3-phenoxypropyl)aminoquinazoline 4-[2-(2,5-Dimethoxyphenoxy)ethyl]aminoquinazoline 4-[2-(3,5-Dimethyl-4-bromophenoxy)ethyl]aminoquinazoline 4-[2-(2,4-Dichloro-6-methylphenoxy)ethyl]aminoquinazoline 4-[2-(2-Trifluoromethyl-4-chlorophenoxy)ethyl]aminoquinazoline 4-[2-(2-n-Butylphenoxy)ethyl]aminoquinazoline 4-[2-(2-tert-Butylphenoxy)ethyl]aminoquinazoline

The compounds of formula (I) may readily be prepared, for example, by the following methods which can be performed under per se known conditions: ##STR2## (In the above formulae, A, B, X, Y and Z are as defined above).

The reaction is preferably carried out in the presence of a solvent and a base.

The nature of the solvent is not critical, provided that it has no adverse effect upon the reaction. Examples of suitable solvents include: Chlorinated or non-chlorinated aromatic, aliphatic or alicyclic hydrocarbons, such as benzene, toluene, xylene, methylnaphthalene, petroleum ether, ligroin, hexane, chlorobenzene, dichlorobenzene, methylene chloride, chloroform, dichloroethane, trichloroethylene and cyclohexane; ethers, such as diethyl ether, ethylene glycol dimethyl ether, tetrahydrofuran and dioxane; ketones, such as acetone and methyl ethyl ketone; alcohols, such as methanol, ethanol and ethylene glycol as well as mixtures thereof with water; and mixtures of the above-mentioned solvents.

Examples of bases include: organic bases, such as triethylamine, pyridine and N,N-diethylaniline; inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate and potassium carbonate.

The reaction temperature is not critical and it ranges usually from ambient to a temperature at which the solvent used refluxes. It is preferable that the reaction is performed with heating in order to shorten the reaction period.

After completion of the reaction, the desired compound may optionally be purified by conventional methods such as recrystallization or chromatography.

Acid addition salts may readily be prepared by introducing an acid into the reaction mixture and then by evaporating the solvent.

Similarly, hydrates may usually be obtained by recrystallizing the desired compound from a solvent containing water.

Preparation of the active ingredient compound of the invention is illustrated by the following Examples:

Preparation 1. Compound No. 19

To a solution of 2.0 g (0.01 mol) of 4,6-dichloroquinazoline in 50 ml of benzene were added 1.0 g (0.01 mol) of triethylamine and 1.7 g (0.01 mol) of 2-(2-chlorophenoxy) ethylamine, and the mixture was refluxed, with stirring, for 3 hours.

After completion of the reaction, the benzene was removed from the reaction mixture by evaporation under reduced pressure, and the crystals which were separated were washed with water and collected by filtration. Recrystallization of the crystals from ethanol gave 2.7 g of 6-chloro-4-[2-(2-chlorophenoxy)ethyl]aminoquinazoline in the form of colorless plates.

m.p. 176.degree..about.178.degree. C.

Elementary analysis (%): Calcd: C, 57.62; H, 3.78; N, 12.69; Found: C, 57.50; H, 3.92; N, 12.57.

Preparation 2. Compound No. 31

To a solution of 1.8 g (0.01 mol) of 4-chloro-6-methylquinazoline in 50 ml of benzene were added 1.0 g (0.01 mol) of triethylamine and 1.7 g (0.01 mol) of 2-(0-methoxyphenoxy)ethylamine, and the mixture was heated, with stirring, at 60.degree..about.70.degree. C. for 5 hours. After completion of the reaction, the benzene was evaporated under reduced pressure and the residue was dissolved in chloroform, washed with water and dried over anhydrous sodium sulfate. The chloroform was evaporated under reduced pressure to leave crystals, which were recrystallized from ethanol, giving 0.9 g of 6-methyl-4-[2-(2-methoxyphenoxy)ethyl]-aminoquinazoline in the form of colorless plates.

m.p. 167.degree..about.169.degree. C.

Elementary analysis (%): Calcd: C, 69.88; H, 6.19; N, 13.58; Found: C, 69.86; H, 6.15; N, 13.60.

Preparation 3. Compound No. 49

To a solution of 2.5 g (0.015 mol) of 4-chloroquinazoline in 50 ml of benzene were added 1.5 g (0.015 mol) of triethylamine and 3.5 g (0.015 mol) of 2-(p-bromophenylthio) ethylamine, and the mixture was heated, with stirring, at 70.degree..about.80.degree. C. for 3 hours. After completion of the reaction, the benzene was evaporated under reduced pressure and the resulting crystals were washed with water, collected by filtration and recrystallized from ethanol, giving 3.0 g of 4-[2-(4-bromophenylthio)ethyl]aminoquinazoline in the form of colorless granules.

m.p. 161.degree..about.163.degree. C.

Elementary analysis (%): Calcd: C, 52.95; H, 3.85; N, 11.41; Found: C, 53.34; H, 3.92; N, 11.66.

Preparation 4. Compound No. 86

To a solution of 3.3 g (0.02 mol) of 4-chloroquinazoline in 50 ml of benzene were added 2.0 g (0.02 mol) of triethylamine and 3.0 g (0.02 mol) of 2-benzyloxyethylamine, and the mixture was heated, with stirring, at 60.degree..about.70.degree. C. for 5 hours. After completion of the reaction, the benzene was evaporated under reduced pressure, and the resulting crystals were washed with water, collected by filtration, dried and recrystallized from benzene/n-hexane, affording 3.7 g of 4-[2-(benzyloxy)ethyl]aminoquinazoline in the form of colorless needles.

m.p. 111.degree..about.113.degree. C.

Elementary analysis (%): Calcd: C, 73.09; H, 6.14; N, 15.04; Found: C, 72.98; H, 6.11; N, 14.69.

Preparation 5. Compound No. 102

To a solution of 2.5 g (0.015 mol) of 4-chloroquinazoline in 50 ml of benzene were added 1.5 g (0.015 mol) of triethylamine and 2.3 g (0.015 mol) of 3-phenoxypropylamine, and the mixture was refluxed for 3 hours.

After completion of the reaction, the benzene was evaporated under reduced pressure and the residue was washed with water, collected by filtration to give crystals. The crystals were recrystallized from 70% ethanol, giving 1.5 g of 4-(3-phenoxypropyl)aminoquinazoline in the form of colorless flakes.

m.p. 129.degree..about.131.degree. C.

Elementary analysis (%): Calcd: C, 73.09; H. 6.14; N, 15.04; Found: C, 72.69; H, 6.24; N, 14.66.

Preparation 6. Compound No. 108

To a solution of 1.7 g (0.008 mol) of 4-chloro-5-nitroquinazoline in 50 ml of benzene were added 0.8 g (0.008 mol) of triethylamine and 1.2 g (0.008 mol) of 3-phenoxypropylamine, and the mixture was refluxed for 3 hours on an oil bath. After cooling, crystals separated were collected by filtration, washed with water and recrystallized from aqueous ethanol, affording 6-nitro-4-(3-phenoxypropyl)aminoquinazoline as the monohydrate in the form of yellow needles.

m.p. 121.degree..about.123.degree. C.

Elementary analysis (%): Calcd: C, 60.38; H, 5.19; N, 16.44; Found: C, 59.65; H, 5.26; N, 16.37.

Preparation 7. Compound No. 208

To a solution of 2.0 g (0.01 mol) of 2,4-dichloroquinazoline in 50 ml of benzene were added 1.0 g (0.01 mol) of triethylamine and 1.8 g (0.01 mol) of 2,2-dimethyl-2-(4-methylphenoxy)-ethylamine and the mixture was stirred at an ambient temperature for 4 hours. After completion of the reaction, the benzene was evaporated under reduced pressure, and the residue was dissolved in chloroform, washed with water and dried over anhydrous sodium sulfate. The chloroform was removed by evaporation under reduced pressure to leave crystals, which were recrystallized from benzene/hexane, affording 2.3 g of 2-chloro-4-[2,2-dimethyl-2-(4-methylphenoxy)ethyl]-aminoquinazoline in the form of a colorless fine powder.

m.p. 121.degree..about.124.degree. C.

Elementary analysis (%): Calcd: C, 66.76; H, 5.90; N, 12.29; Found: C, 66.52; H, 6.04; N, 11.93.

Preparation 8. Compound No. 222

To a solution of 1.7 g (0.01 mol) of 4-chloroquinazoline in 50 ml of benzene were added 1.0 g (0.01 mol) of triethylamine and 1.8 g (0.01 mol) of 5-phenoxypentylamine, and the mixture was refluxed for 3 hours. After completion of the reaction, the benzene was evaporated under reduced pressure to leave crystals, which were washed with water, collected by filtration and recrystallized from aqueous ethanol, giving 0.6 g of 4-(5-phenoxypentyl)aminoquinazoline in the form of colorless flakes.

m.p. 106.degree..about.108.degree. C.

Elementary analysis (%): Calcd: C, 74.26; H, 6.84; N, 13.68; Found: C, 74.95; H, 6.89; N, 13.75.

2.5 g of the 4-(5-phenoxypentyl)aminoquinazoline obtained according to the process were dissolved in 100 ml of ethanol, and 2 g of 36% hydrochloric acid were added. The ethanol was removed by evaporation under reduced pressure and the resulting residue was dried, recrystallized from aqueous ethanol, giving 4-(5-phenoxypentyl)aminoquinazoline in the form of the hydrochloride melting at 183.degree..about.186.degree. C.

Following the methods described in Preparations 1 to 8, the following compounds were obtained:

4-(2-Methoxyethyl)aminoquinazoline m.p. 127.degree..about.128.degree. C. 4-(2-Ethoxyethyl)aminoquinazoline m.p. 112.degree..about.113.degree. C. 4-(2-Ethylthioethyl)aminoquinazoline m.p. 116.degree..about.118.degree. C. 2-Chloro-4-(2-ethoxyethyl)aminoquinazoline m.p. 93.degree..about.95.degree. C. 2-Chloro-4-(2-ethylthioethyl)aminoquinazoline m.p. 119.degree..about.121.degree. C. 6-Chloro-4-(2-ethoxyethyl)aminoquinazoline m.p. 125.degree..about.127.degree. C. 4-(2-n-Propylthioethyl)aminoquinazoline m.p. 95.degree..about.98.degree. C. 4-(2-Phenoxyethyl)aminoquinazoline m.p. 183.degree..about.185.degree. C. 4-(2-Phenylthioethyl)aminoquinazoline m.p. 137.degree..about.139.degree. C. 2-Chloro-4-(2-phenoxyethyl)aminoquinazoline m.p. 172.degree..about.174.degree. C. 2-Chloro-4-(2-phenylthioethyl)aminoquinazoline m.p. 210.degree..about.212.degree. C. 6-Chloro-4-(2-phenoxyethyl)aminoquinazoline m.p. 155.degree..about.158.degree. C. 6-Methyl-4-(2-phenoxyethyl)aminoquinazoline m.p. 138.degree..about.140.degree. C. 4-[2-(2-Chlorophenoxy)ethyl]aminoquinazoline m.p. 161.degree..about.163.degree. C. 4-[2-(2-Bromophenoxy)ethyl]aminoquinazoline m.p. 164.degree..about.166.degree. C. 4-[2-(2-Iodophenoxy)ethyl]aminoquinazoline m.p. 161.degree..about.163.degree. C. 4-[2-(2-Fluorophenoxy)ethyl]aminoquinazoline m.p. 164.degree..about.166.degree. C. 2-Chloro-4-[2-(2-chlorophenoxy)ethyl]aminoquinazoline m.p. 169.degree..about.171.degree. C. 4-[2-(2-Methylphenoxy)ethyl]aminoquinazoline m.p. 138.degree..about.140.degree. C. 4-[2-(2-Methylphenylthio)ethyl]aminoquinazoline m.p. 149.degree..about.151.degree. C. 2-Chloro-4-[2-(2-methylphenoxy)ethyl]aminoquinazoline m.p. 176.degree..about.178.degree. C. 6-Chloro-4-[2-(2-methylphenoxy)ethyl]aminoquinazoline m.p. 168.degree..about.171.degree. C. 6-Methyl-4-[2-(2-methylphenoxy)ethyl]aminoquinazoline m.p. 161.degree..about.164.degree. C. 2-Chloro-4-[2-(2-methylphenylthio)ethyl]aminoquinazoline m.p. 194.degree..about.196.degree. C. 4-[2-(2-Ethylphenoxy)ethyl]aminoquinazoline m.p. 134.degree..about.135.degree. C. 4-[2-(2-Isopropylphenoxy)ethyl]aminoquinazoline m.p. 132.degree..about.134.degree. C. 4-[2-(2-sec-Butylphenoxy)ethyl]aminoquinazoline m.p. 128.degree..about.130.degree. C. 4-[2-(2-Methoxyphenoxy)ethyl]aminoquinazoline m.p. 148.degree..about.152.degree. C. 4-[2-(2-Ethoxyphenoxy)ethyl]aminoquinazoline.monohydrate m.p. 111.degree..about.113.degree. C. 6-Chloro-4-[2-(2-ethoxyphenoxy)ethyl]aminoquinazoline.monohydrate m.p. 154.degree..about.156.degree. C. 4-[2-(2-Phenylphenoxy)ethyl]aminoquinazoline m.p. 137.degree..about.140.degree. C. 4-[2-(3-Chlorophenoxy)ethyl]aminoquinazoline m.p. 193.degree..about.195.degree. C. 6-Methyl-4-[2-(3-chlorophenoxy)ethyl]aminoquinazoline m.p. 150.degree..about.152.degree. C. 4-[2-(3-Methylphenoxy)ethyl]aminoquinazoline m.p. 184.degree..about.186.degree. C. 4-[2-(3-Methylphenylthio)ethyl]aminoquinazoline m.p. 131.degree..about.133.degree. C. 2-Chloro-4-[2-(3-methylphenoxy)ethyl]aminoquinazoline m.p. 162.degree..about.164.degree. C. 2-Chloro-4-[2-(3-methylphenylthio)ethyl]aminoquinazoline m.p. 154.degree..about.156.degree. C. 4-[2-(3-Trifluoromethylphenoxy)ethyl]aminoquinazoline m.p. 161.degree..about.163.degree. C. 4-[2-(4-Chlorophenoxy)ethyl]aminoquinazoline m.p. 191.degree..about.193.degree. C. 4-[2-(4-Chlorophenylthio)ethyl]aminoquinazoline m.p. 147.degree..about.149.degree. C. 4-[2-(4-Bromophenoxy)ethyl]aminoquinazoline m.p. 161.degree..about.163.degree. C. 4-[2-(4-Fluorophenoxy)ethyl]aminoquinazoline m.p. 189.degree..about.190.degree. C. 4-[2-(4-Methylphenoxy)ethyl]aminoquinazoline m.p. 153.degree..about.155.degree. C. 4-[2-(4-Methylphenylthio)ethyl]aminoquinazoline m.p. 134.degree..about.136.degree. C. 2-Chloro-4-[2-(4-methylphenoxy)ethyl]aminoquinazoline m.p. 161.degree..about.163.degree. C. 2-Chloro-4-[2-(4-methylphenylthio)ethyl]aminoquinazoline m.p. 160.degree..about.165.degree. C. 6-Methyl-4-[2-(4-methylphenoxy)ethyl]aminoquinazoline m.p. 143.degree..about.145.degree. C. 4-[2-(4-tert-Butylphenoxy)ethyl]aminoquinazoline m.p. 138.degree..about.143.degree. C. 4-[2-(4-Methoxyphenoxy)ethyl]aminoquinazoline m.p. 142.degree..about.144.degree. C. 4-[2-(2,4-Dichlorophenoxy)ethyl]aminoquinazoline m.p. 170.degree..about.172.degree. C. 4-[2-(2,4-Dibromophenoxy)ethyl]aminoquinazoline m.p. 161.degree..about.163.degree. C. 6-Chloro-4-[2-(2,4-dichlorophenoxy)ethyl]aminoquinazoline m.p. 187.degree..about.188.degree. C. 4-[2-(2-Methyl-4-chlorophenoxy)ethyl]aminoquinazoline m.p. 164.degree..about.166.degree. C. 2-Chloro-4-[2-(2-methyl-4-chlorophenoxy)ethyl]aminoquinazoline m.p. 179.degree..about.181.degree. C. 4-[2-(2,4-Dimethylphenoxy)ethyl]aminoquinazoline m.p. 164.degree..about.167.degree. C. 4-[2-(2-Chloro-4-methoxyphenoxy)ethyl]aminoquinazoline m.p. 124.degree..about.126.degree. C. 6-Chloro-4-[2-(2,5-dimethylphenoxy)ethyl]aminoquinazoline m.p. 164.degree..about.167.degree. C. 4-[2-(2,6-Dimethylphenoxy)ethyl]aminoquinazoline m.p. 132.degree..about.134.degree. C. 2-Chloro-4-[2-(2,6-dimethylphenoxy)ethyl]aminoquinazoline m.p. 169.degree..about.171.degree. C. 4-[2-(3-Methyl-4-methylthiophenoxy)ethyl]aminoquinazoline m.p. 171.degree..about.173.degree. C. 4-(2-(3,5-Dimethylphenoxy)ethyl]aminoquinazoline m.p. 183.degree..about.185.degree. C. 2-Chloro-4-[2-(3,5-dimethylphenoxy)ethyl]aminoquinazoline m.p. 186.degree..about.188.degree. C. 6-Chloro-4-[2-(3,5-dimethylphenoxy)ethyl]aminoquinazoline m.p. 209.degree..about.211.degree. C. 4-[2-(2,4,5-Trichlorophenoxy)ethyl]aminoquinazoline m.p. 176.degree..about.178.degree. C. 6-Chloro-4-[2-(2,4,5-trichlorophenoxy)ethyl]aminoquinazoline m.p. 198.degree..about.202.degree. C. 4-[2-(2,4,6-Trichlorophenoxy)ethyl]aminoquinazoline m.p. 170.degree..about.172.degree. C. 4-[2-(2,4,6-Triiodophenoxy)ethyl]aminoquinazoline m.p. 185.degree..about.187.degree. C. 4-[2-(2,4,6-Tribromophenoxy)ethyl]aminoquinazoline m.p. 181.degree..about.183.degree. C. 4-[2-(1-Naphthoxy)ethyl]aminoquinazoline m.p. 163.degree..about.165.degree. C. 6-Chloro-4-[2-(1-naphthoxy)ethyl]aminoquinazoline m.p. 165.degree..about.167.degree. C. 4-[2-(Benzylthio)ethyl]aminoquinazoline m.p. 111.degree..about.113.degree. C. 2-Chloro-4-[2-(benzylthio)ethyl]aminoquinazoline m.p. 107.degree..about.109.degree. C. 4-(3-Methoxypropyl)aminoquinazoline m.p. 105.degree..about.107.degree. C. 4-(3-Ethoxypropyl)aminoquinazoline m.p. 101.degree..about.103.degree. C. 2-Chloro-4-(3-ethoxypropyl)aminoquinazoline m.p. 92.degree..about.95.degree. C. 6-Nitro-4-(3-ethoxypropyl)aminoquinazoline m.p. 141.degree..about.143.degree. C. 4-(3-Isopropoxypropyl)aminoquinazoline m.p. 84.degree..about.86.degree. C. 4-(3-n-Butoxypropyl)aminoquinazoline m.p. 77.degree..about.79.degree. C. 2-Chloro-4-(3-n-butoxypropyl)aminoquinazoline m.p. 86.degree..about.88.degree. C. 4-[3-(2-Ethylhexyloxy)propyl]aminoquinazoline m.p. 36.degree..about.40.degree. C. 6-Nitro-4-[3-(2-ethylhexyloxy)propyl]aminoquinazoline m.p. 55.degree..about.58.degree. C. 4-(3-Phenylthiopropyl)aminoquinazoline m.p. 103.degree..about.105.degree. C. 2-Chloro-4-(3-phenoxypropyl)aminoquinazoline m.p. 118.degree..about.120.degree. C. 2-Chloro-4-(3-phenylthiopropyl)aminoquinazoline m.p. 86.degree..about.89.degree. C. 6-Methyl-4-(3-phenoxypropyl)aminoquinazoline m.p. 121.degree..about.123.degree. C. 6-Methyl-4-(3-phenylthiopropyl)aminoquinazoline m.p. 121.degree..about.123.degree. C. 4-[3-(2-Chlorophenoxy)propyl]aminoquinazoline m.p. 144.degree..about.145.degree. C. 4-[3-(2-Methylphenoxy)propyl]aminoquinazoline m.p. 147.degree..about.149.degree. C. 4-[3-(2-Methylphenylthio)propyl]aminoquinazoline m.p. 99.degree..about.102.degree. C. 4-[3-(2-Methoxyphenoxy)propyl]aminoquinazoline m.p. 138.degree..about.139.degree. C. 4-[3-(3-Chlorophenoxy)propyl]aminoquinazoline m.p. 145.degree..about.147.degree. C. 4-[3-(3-Methylphenoxy)propyl]aminoquinazoline m.p. 153.degree..about.155.degree. C. 4-[3-(3-Methylphenylthio)propyl]aminoquinazoline m.p. 73.degree..about.76.degree. C. 2-Chloro-4-[3-(3-methylphenoxy)propyl]aminoquinazoline m.p. 96.degree..about.99.degree. C. 2-Chloro-4-[3-(3-methylphenylthio)propyl]aminoquinazoline m.p. 70.degree..about.73.degree. C. 4-[3-(4-Chlorophenoxy)propyl]aminoquinazoline m.p. 148.degree..about.150.degree. C. 2-Chloro-4-[3-(4-chlorophenoxy)propyl]aminoquinazoline m.p. 131.degree..about.133.degree. C. 4-[3-(4-Methylphenoxy)propyl]aminoquinazoline m.p. 151.degree..about.152.degree. C. 4-[3-(4-Methylphenylthio)propyl]aminoquinazoline m.p. 129.degree..about.131.degree. C. 2-Chloro-4-[3-(4-methylphenylthio)propyl]aminoquinazoline m.p. 82.degree..about.85.degree. C. 4-[3-(4-Methoxyphenoxy)propyl]aminoquinazoline m.p. 136.degree..about.138.degree. C. 4-[3-(2,5-Dimethylphenoxy)propyl]aminoquinazoline m.p. 142.degree..about.144.degree. C. 4-[3-(2-Methyl-4-chlorophenoxy)propyl]aminoquinazoline m.p. 178.degree..about.181.degree. C. 4-[3-(2-Chloro-4-methoxyphenoxy)propyl]aminoquinazoline m.p. 166.degree..about.169.degree. C. 4-[3-(3-Methyl-4-chlorophenoxy)propyl]aminoquinazoline m.p. 137.degree..about.139.degree. C. 4-[3-(3,5-Dimethylphenoxy)propyl]aminoquinazoline m.p. 116.degree..about.118.degree. C. 4-[3-(1-Naphthoxy)propyl]aminoquinazoline m.p. 132.degree..about.134.degree. C. 4-(1-Methyl-2-phenoxyethyl)aminoquinazoline m.p. 125.degree..about.128.degree. C. 2-Chloro-4-(1-methyl-2-phenoxyethyl)aminoquinazoline m.p. 168.degree..about.170.degree. C. 6-Methyl-4-(1-methyl-2-phenoxyethyl)aminoquinazoline m.p. 150.degree..about.152.degree. C. 4-[1-Methyl-2-(2-methylphenoxy)ethyl]aminoquinazoline m.p. 134.degree..about.136.degree. C. 4-[1-Methyl-2-(2-methoxyphenoxy)ethyl]aminoquinazoline m.p. 165.degree..about.167.degree. C. 4-[1-Methyl-2-(3-chlorophenoxy)ethyl]aminoquinazoline m.p. 163.degree..about.166.degree. C. 4-[1-Methyl-2-(3-methylphenoxy)ethyl]aminoquinazoline m.p. 130.degree..about.132.degree. C. 4-[1-Methyl-2-(4-chlorophenoxy)ethyl]aminoquinazoline m.p. 156.degree..about.159.degree. C. 2-Chloro-4-[1-methyl-2-(4-chlorophenoxy)ethyl]aminoquinazoline m.p. 125.degree..about.128.degree. C. 4-[1-Methyl-2-(4-methylphenoxy)ethyl]aminoquinazoline m.p. 171.degree..about.173.degree. C. 2-Chloro-4-[1-methyl-2-(4-methylphenoxy)ethyl]aminoquinazoline m.p. 139.degree..about.141.degree. C. 4-(2-Methyl-2-phenoxyethyl)aminoquinazoline m.p. 162.degree..about.164.degree. C. 2-Chloro-4-(2-methyl-2-phenoxyethyl)aminoquinazoline m.p. 144.degree..about.146.degree. C. 4-[2-Methyl-2-(2-chlorophenoxy)ethyl]aminoquinazoline m.p. 151.degree..about.153.degree. C. 4-[2-Methyl-2-(2-methylphenoxy)ethyl]aminoquinazoline m.p. 152.degree..about.154.degree. C. 2-Chloro-4-[2-methyl-2-(2-methylphenoxy)ethyl]aminoquinazoline m.p. 122.degree..about.125.degree. C. 4-[2-Methyl-2-(2-methoxyphenoxy)ethyl]aminoquinazoline m.p. 135.degree..about.138.degree. C. 4-[2-Methyl-2-(3-chlorophenoxy)ethyl]aminoquinazoline m.p. 140.degree..about.142.degree. C. 4-[2-Methyl-2-(3-methylphenoxy)ethyl]aminoquinazoline m.p. 123.degree..about.126.degree. C. 4-[2-Methyl-2-(4-chlorophenoxy)ethyl]aminoquinazoline m.p. 165.degree..about.168.degree. C. 2-Chloro-4-[2-methyl-2-(4-chlorophenoxy)ethyl]aminoquinazoline m.p. 160.degree..about.162.degree. C. 4-[2-Methyl-2-(4-methylphenoxy)ethyl]aminoquinazoline m.p. 163.degree..about.164.degree. C. 2-Chloro-4-[2-methyl-2-(4-methylphenoxy)ethyl]aminoquinazoline m.p. 138.degree..about.141.degree. C. 4-(4-Phenoxybutyl)aminoquinazoline.monohydrate m.p. 90.degree..about.93.degree. C. 6-Methyl-4-(4-phenoxybutyl)aminoquinazoline m.p. 110.degree..about.112.degree. C. 4-[4-(2-Chlorophenoxy)butyl]aminoquinazoline m.p. 151.degree..about.153.degree. C. 4-[4-(2-Methylphenoxy)butyl]aminoquinazoline m.p. 152.degree..about.153.degree. C. 4-[4-(2-Methoxyphenoxy)butyl]aminoquinazoline m.p. 135.degree..about.137.degree. C. 4-[4-(3-Methylphenoxy)butyl]aminoquinazoline m.p. 110.degree..about.112.degree. C. 4-[4-(4-Methylphenoxy)butyl]aminoquinazoline m.p. 121.degree..about.123.degree. C. 4-(2-Ethyl-2-phenoxyethyl)aminoquinazoline m.p. 158.degree..about.160.degree. C. 4-(2,2-Dimethyl-2-phenoxyethyl)aminoquinazoline m.p. 98.degree..about.100.degree. C. 2-Chloro-4-(2,2-dimethyl-2-phenoxyethyl)aminoquinazoline m.p. 132.degree..about.134.degree. C. 4-[2,2-Dimethyl-2-(2-chlorophenoxy)ethyl]aminoquinazoline m.p. 89.degree..about.91.degree. C. 4-[2,2-Dimethyl-2-(2-methylphenoxy)ethyl]aminoquinazoline m.p. 96.degree..about.99.degree. C. 2-Chloro-4-[2,2-dimethyl-2-(2-methylphenoxy)ethyl]aminoquinazoline m.p. 110.degree..about.112.degree. C. 4-[2,2-Dimethyl-2-(2-methoxyphenoxy)ethyl]aminoquinazoline m.p. 103.degree..about.105.degree. C. 4-[2,2-Dimethyl-2-(3-chlorophenoxy)ethyl]aminoquinazoline m.p. 111.degree..about.113.degree. C. 4-[2,2-Dimethyl-2-(3-methylphenoxy)ethyl]aminoquinazoline m.p. 97.degree..about.100.degree. C. 2-Chloro-4-[2,2-dimethyl-2-(3-methylphenoxy)ethyl]aminoquinazoline m.p. 103.degree..about.106.degree. C. 4-[2,2-Dimethyl-2-(4-chlorophenoxy)ethyl]aminoquinazoline m.p. 104.degree..about.106.degree. C. 4-[2,2-Dimethyl-2-(4-methylphenoxy)ethyl]aminoquinazoline m.p. 92.degree..about.94.degree. C. 4-[5-(2-Chlorophenoxy)pentyl]aminoquinazoline m.p. 115.degree..about.117.degree. C. 4-[5-(2-Methylphenoxy)pentyl]aminoquinazoline m.p. 96.degree..about.98.degree. C. 4-[5-(2-Methoxyphenoxy)pentyl]aminoquinazoline m.p. 104.degree..about.106.degree. C. 4-[5-(3-Methylphenoxy)pentyl]aminoquinazoline m.p. 113.degree..about.115.degree. C. 4-[5-(4-Methylphenoxy)pentyl]aminoquinazoline m.p. 128.degree..about.130.degree. C. 4-(6-Phenoxyhexyl)aminoquinazoline m.p. 105.degree..about.108.degree. C. 4-(7-Phenoxyheptyl)aminoquinazoline m.p. 83.degree..about.86.degree. C. 4-(8-Phenoxyoctyl)aminoquinazoline m.p. 74.degree..about.78.degree. C. 4-[2-(2-n-Propylphenoxy)ethyl]aminoquinazoline m.p. 74.degree..about.78.degree. C. 6-Methyl-4-[4-(2-chlorophenoxy)butyl]aminoquinazoline m.p. 113.degree..about.116.degree. C. 4-[2-(2-Methoxy-4-methylphenoxy)ethyl]aminoquinazoline m.p. 155.degree..about.156.degree. C. 4-[2-(3-Methoxyphenoxy)ethyl]aminoquinazoline m.p. 165.degree..about.166.degree. C. 4-[2-(2-Methoxy-4-chlorophenoxy)ethyl]aminoquinazoline m.p. 163.degree..about.166.degree. C. 4-[2-(2-Methyl-3-chlorophenoxy)ethyl]aminoquinazoline m.p. 154.degree..about.156.degree. C. 2-Methyl-4-(3-phenoxypropyl)aminoquinazoline m.p. 111.degree..about.115.degree. C. 4-[2-(2,5-Dimethoxyphenoxy)ethyl]aminoquinazoline m.p. 178.degree..about.180.degree. C. 4-[2-(3,5-Dimethyl-4-bromophenoxy)ethyl]aminoquinazoline m.p. 218.degree..about.220.degree. C. 4-[2-(2,4-Dichloro-6-methylphenoxy)ethyl]aminoquinazoline m.p. 165.degree..about.167.degree. C. 4-[2-(2-Trifluoromethyl-4-chlorophenoxy)ethyl]aminoquinazoline m.p. 159.degree..about.162.degree. C. 6-Chloro-4-[2-(2-Chlorophenoxy)ethyl]aminoquinazoline m.p. 176.degree..about.178.degree. C. 4-[2-(2-n-Butoxyphenoxy)ethyl]aminoquinazoline m.p. 89.degree..about.92.degree. C. 4-[2-(2-Trifluoromethylphenoxy]ethyl]aminoquinazoline m.p. 143.degree..about.145.degree. C. 4-[2-(4-Bromopherylthio)ethyl]aminoquinazoline m.p. 162.degree..about.163.degree. C. 4-[2-(4-Isopropoxyphenoxy)ethyl]aminoquinazoline m.p. 148.degree..about.151.degree. C. 4-[2-(2,4-Dibromophenoxy)ethyl]aminoquinazoline m.p. 161.degree..about.163.degree. C. 6-Chloro-4-[2-(2,4,6-trichlorophenoxy)ethyl]aminoquinazoline m.p. 185.degree..about.187.degree. C. 4-[2-(2,3,6-Trimethylphenoxy)ethyl]aminoquinazoline m.p. 155.degree..about.158.degree. C. 4-[2-(Benzyloxy)ethyl]aminoquinazoline m.p. 111.degree..about.113.degree. C. 4-(3-Phenoxypropyl)aminoquinazoline m.p. 129.degree..about.131.degree. C. 6-Nitro-4-(3-phenoxypropyl)aminoquinazoline m.p. 121.degree..about.123.degree. C. 2-Chloro-4-[3-(4-chlorophenoxy)propyl]aminoquinazoline m.p. 131.degree..about.133.degree. C. 2-Chloro-4-[2,2-dimethyl-2(4-methylphenoxy)ethyl]aminoquinazoline m.p. 121.degree..about.124.degree. C. 4-(5-Phenoxypentyl)aminoquinazoline m.p. 106.degree..about.108.degree. C. 4-[6-(2-Methylphenoxy)hexyl]aminoquinazoline m.p. 90.degree..about.92.degree. C. 4-[7-(2-Methylphenoxy)heptyl]aminoquinazoline m.p. 88.degree..about.91.degree. C. 4-[8-(2-Methylphenoxy)octyl]aminoquinazoline m.p. 70.degree..about.73.degree. C. 4-[12-(2-Methylphenoxy)dodecyl]aminoquinazoline m.p. 66.degree..about.70.degree. C. 4-[2-(2-n-Butylphenoxy)ethyl]aminoquinazoline m.p. 150.degree..about.163.degree. C. 4-[2-(2-tert-Butylphenoxy)ethyl]aminoquinazoline m.p. 158.degree..about.160.degree. C.

The compounds in this invention may be formulated for use with the preparations commonly employed as an agricultural fungicide, for example, powdery dusts, coarse dusts, fine granules, granules, wettable powders, emulsifiable concentrates, aqueous liquids, water soluble powders, oil suspensions and so on, with admixture of a carrier and, if required, other auxiliary agents. The carrier as used herein means a synthetic or natural and inorganic or organic substance that is mixed with an active compound and can assist an active compound in its arrival to the site to be treated and make it easy to store, transport or handle.

As suitable solid carriers may be mentioned inorganic substances such as clays, which may be represented by Kaolinite, Montmorillonite or Attapulgite, talc, mica, pyrophyllite, pumice, vermiculite, gypsum, calcium carbonate, dolomite, diatomaceous earth, magnesium carbonate, apatite, zeolite, silicic anhydride, synthetic calcium silicate and the like, vegetable organic substances such as soybean meal, tobacco powder, walnut powder, wheat flour, wood meal, starch, crystalline cellulose and the like, synthetic or natural high polymer compounds such as cumarone resin, petroleum resin, alkyl resin, polyvinyl chloride, polyalkylene glycol, ketone resin, ester gum, copal gum, dammar gum, and the like, waxes such as carnauba wax, beeswax and the like, or urea.

As suitable liquid media or carriers may be mentioned paraffin or naphthene hydrocarbons such as kerosine, mineral oil, spindle oil, white oil and the like, aromatic hydrocarbons such as benzene, toluene, xylene, ethylbenzene, cumene, methylnaphthalene and the like, chlorinated hydrocarbons such as carbon tetra chloride, chloroform, trichloroethylene, monochlorobenzene, o-chlorotoluene and the like, ethers such as dioxane, tetrahydrofuran and the like, ketones such as acetone, methyl ethyl ketone, diisobutylketone, cyclohexanone, acetophenone, isophorone and the like, esters such as ethyl acetate, amyl acetate, ethylene glycol acetate, diethylene glycol acetate, dibutyl maleate, diethyl succinate and the like, alcohols such as methanol, n-hexanol, ethylene glycol, diethylene glycol, cyclohexanol, benzyl alcohol and the like, ether alcohols such as ethylene glycol ethyl ether, ethylene glycol phenyl ether, diethylene glycol ethyl ether, diethylene glycol butyl ether and the like, polar solvents such as dimethylformamide, dimethylsulfoxide and the like, or water.

As the surface active agents used for emulsifying, dispersing, wetting, spreading, binding, controlling disintegration, stabilizing active ingredient, improving fluidity, rust proofing and so on may be utilized any of non-ionic, anionic, cationic and amphoteric ones, but non-ionic and/or anionic agents are usually employed. As suitable non-ionic surface active agents may be mentioned, for example, polymerization adducts of ethylene oxide and higher alcohols such as lauryl alcohol, stearyl alcohol, oleyl alcohol and the like, polymerization adducts of ethylene oxide and alkyl phenols such as isooctyl phenol, nonyl phenol and the like, polymerization adducts of ethylene oxide and alkyl naphthols such as butyl naphthol, octyl naphthol and the like, polymerization adducts of ethylene oxide and higher fatty acids such as palmitic acid, stearic acid, oleic acid and the like, polymerization adducts of ethylene oxide and mono- or di-alkyl phosphoric acids such as stearyl phosphoric acid, dilauryl phosphoric acid and the like, polymerization adducts of ethylene oxide and amines such as dodecyl amine, stearic acid amide and the like, polymerization adducts of ethylene oxide and higher fatty acid esters of polyhydric alcohols such as sorbitan and said fatty acid esters, polymerization adducts of ethylene oxide to propylene oxide and so on. As suitable anionic surface active agents may be mentioned, for example, alkyl sulfate salts such as sodium lauryl sulfate, oleyl sulfate amine salt and the like, alkyl sulfonate salts such as sodium dioctyl sulfosuccinate, sodium 2-ethylhexene sulfonate and the like, aryl sulfonate salts such as sodium isopropylnaphthalene sulfonate, sodium methylenebisnaphthalene sulfonate, sodium ligninsulfonate, sodium dodecylbenzene sulfonate and the like.

Moreover, the agricultural fungicidal compositions of this invention may be used in combination with high molecular compounds or other auxiliary agents such as casein, gelatin, albumin, glue, sodium alginate, carboxymethyl cellulose, methyl cellulose, hydroxyethyl cellulose, polyvinyl alcohol and the like for improving properties and increasing biological effects thereof.

The above-mentioned carriers and various auxiliary agents may be optionally utilized alone or in combination for desired purposes, with consideration for the type of preparation, application and other factors.

Dusts usually contain, for example, 1 to 25 parts by weight of the active compound and the remainder is a solid carrier.

Wettable powders usually contain, for example, 25-90 parts by weight of the active compound and the remainder is a solid carrier and a dispersing and wetting agent, if required, together with a protective colloidal agent, a thixotropic agent, an anti-foaming agent and the like.

Granules usually contain 1-35 parts by weight of the active compound and a major portion of the remainder is a solid carrier. The active compound is homogeneously admixed with the solid carrier or adhered or adsorbed on the carrier surface and the size of a granule is about 0.2-1.5 mm.

Emulsifiable concentrates usually contain, for example, 5-50 parts by weight of the active compound and about 5-20 parts by weight of an emulsifying agent, the remainder being a liquid carrier, if required, together with a corrosive inhibitor.

The fungicidal compositions of this invention which are formulated into various types of preparations as above, may be applied in a paddy or upland field at 1-5000 g, preferably 10-1000 g of the active ingredient per 10 ares for pre- or post-emergence foliage spraying or soil drenching or spraying onto water to control diseases effectively.

Further, the fungicidal compositions of this invention, when employed for seed disinfection or coating, may effectively control soil-borne or seed infectious diseases by coating seeds at 0.1-2%, preferably 0.2-0.5%, of the active ingredient per weight of the seed.

The fungicidal compositions of this invention may be preferably combined with other fungicides for broader fungicidal spectra and, in some cases, a synergistic effect is expectable.

As examples of such other fungicides may be, for instance, carbamate type fungicides such as 3,3'-ethylene-bis(tetrahydro-4,6-dimethyl-2H-1,3,5-thiadiazine-2-thione; zinc or manganese ethylenebisdithiocarbamate; bis(dimethyldithiocarbamoyl)disulfide; zinc propylenebisdithiocarbamate; bis(dimethyldithiocarbamoyl)ethylenediamine; nickel dimethyldithiocarbamate; methyl 1-(butylcarbamoyl)-2-benzimidazolcarbamate; 1,2-bis(3-methoxycarbonyl-2-thioureido)benzene; phosphorous type fungicides such as O,O-diisopropyl-S-benzylphosphorothioate; O-ethyl-S,S-diphenyldithiophosphate and the like, dicarboximide type fungicides such as N-trichloromethylthio-4-cyclohexene-1,2-dicarboximide; N-tetrachloroethylthio-4-cyclohexene-1,2-dicarboximide and the like, oxazine type fungicides such as 5,6-dihydro-2-methyl-1,4-oxazine-3-carboxanilide-4,4-dioxide; 5,6-dihydro-2-methyl-1,4-oxazine-3-carboxanilide and the like, naphthoquinone type fungicides such as 2,3-dichloro-1,4-naphthoquinone and the like, other fungicides such as pentachloronitrobenzene; 3-hydroxy-5-methylisoxazole; N-(2,3-dichlorophenyl)tetrachlorophthalamic acid; 5-ethoxy-3-trichloromethyl-1,2,4-thiadiazole; 2,4,6-trichloro-6-(o-chloroanilino)-1,3,5-triazine; 2,3-dicyano-1,4-dithio-anthraquinone; copper 8-quinolate; Validamycin; cycloheximide; iron methanearsonate; tetrachloroisophthalonitrile; 2-(1-methylpropyl)-4,6-dinitrophenyl .beta.,.beta.-dimethylacrylate; triphenyltinhydroxide; Polyoxin; Phytomycin, Kasugamycin; Blasticidin S; 4,5,6,7-tetrachlorophthalide and the like, but they are not critical.

The fungicidal compositions of the invention may also be applied in a mixture with insecticides as illustratively given below: phosphorus type insecticides such as O,O-diethyl O-(2-isopropyl-4-methyl-6-pyrimidinyl)phosphorothioate; O,O-diethyl S-2-[(ethylthio)ethyl]phosphorodithioate; O,O-dimethyl O-(3-methyl-4-nitrophenyl)thiophosphate; O,O-dimethyl S-(N-methylcarbamoylmethyl)phosphorodithioate; O,O-dimethyl S-(N-methyl-N-formylcarbamoylmethyl)phosphorodithioate; O,O-dimethyl S-2-(ethylthio)ethylphosphorodithioate; O,O-dimethyl-1-hydroxy-2,2,2-trichloroethylphosphonate; O,O-diethyl-O-(5-phenyl-3-isoxazolyl)phosphorothioate; methyl(4-bromo-2,5-dichlorophenyl)phenylphosphonothioate; O,O-dimethyl-O-(3-methyl-4-methylmercaptophenyl)thiophosphate; O-ethyl-O-p-cyanophenyl phenylphosphonothioate; O,O-diethyl S-(1,2-dicarboethoxyethyl)phosphorodithioate; 2-chloro-1-(2,4,5-trichlorophenyl) vinyldimethyl phosphate; 2-chloro-1-(2,4-dichlorophenyl)vinyldimethyl phosphate; O,O-dimethyl O-p-cyanophenyl phosphorothioate; 2,2-dichlorovinyl dimethyl phosphate; O,O-diethyl O-2,4-dichlorophenyl phosphorothioate; ethyl mercaptophenylacetate O,O-dimethyl phosphorodithioate; S-[(6-chloro-2-oxo-3-benzoxazolinyl)-methyl]O,O-diethylphosphorodithioate; 4-mercaptothiophenyl dipropylphosphate; 2-chloro-1-(2,4-dichlorophenyl)vinyl diethylphosphate; O,O-diethyl-O-(3-oxo-2-phenyl-2H-pyridazin-6-yl)phosphorothioate; O,O-dimethyl S-(1-methyl-2-ethylsulfinyl)-ethyl phosphorothiolate; O,O-dimethyl S-phthalimidomethyl phosphoroditioate; dimethylmethylcarbamoylethylthioethyl thiophosphorothiolate; O,O-diethyl S-(N-ethoxycarbonyl-N-methylcarbamoylmethyl) phosphorodithioate; O,O-dimethyl-S-[2-methoxy-1,3,4-thiadiazol-5(4H)-onyl-(4)-methyl] dithiophosphate; 2-methoxy-4H-1,3,2-benzodioxaphosphorin 2-sulfide; O,O-diethyl-O-(3,5,6-trichloro-2-pyridyl)phosphorothioate; O-ethyl-O-2,4-dichlorophenyl thionobenzene phosphonate; S-[4,6-diamino-S-triazin-2-yl-methyl]-O,O-dimethyl phosphorodithioate; O-ethyl O-p-nitrophenylphenylphosphorothioate; O,S-dimethyl-N-acetyl phosphoroamidothioate or the like; carbamate type insecticides such as 1-naphthyl N-methylcarbamate; S-methyl-N-[methylcarbamoyloxy]thioacetoimidate; m-tolyl methylcarbamate; 3,4xylyl methylcarbamate; 3,5-xylyl methylcarbamate; 2-sec-butylphenyl-N-methylcarbamate; 2-isopropoxyphenyl-N-methylcarbamate; 1,3-bis(carbamoylthio)-2-(N,N-dimethylamino)propane hydrochloride; and the like, other insecticides such as N,N-dimethyl-N'-(2-methyl-4-chlorophenyl) formamidine hydrochloride, nicotine sulfate, Milbemycin, 6-methyl-2,3-quinoxalinedithiocyclic S,S-dithiocarbonate, 2,4-dinitro-6-sec-butylphenyl dimethylacrylate; 1,1-bis(p-chlorophenyl)-2,2,2-trichloroethanol; 2-(p-tert-butylphenoxy)isopropyl-2'-chloroethylsulfite; azoxybenzene; di-(p-chlorophenyl)cyclopropyl carbinol; isopropyl-4,4'-dichlorobenzylate; ethyl-4,4'-dichlorobenzylate; or machine oil and the like.

The fungicidal composition of this invention can be used with a controlling agent against rice blast, Helminthosporium leaf spot, bacterial leaf blight, rice stem borer, planthopper and/or leafhopper to save labor. The agricultural chemicals, which may be used with the present fungicidal composition, are as mentioned hereinabove. The combination ratio of these agents may vary depending upon diseases or insects to be controlled and preparation forms to be used, these agents are prepared and applied with an effective amount of active ingredients required for controlling. In particular, dusts and fine granules are preferable for controlling rice plant diseases and soil treatment.

Examples of the agricultural fungicidal composition of this invention will be given below. All parts are given by weight unless otherwise stated.

Fomulation 1. Dusts

Five parts of the compound having compound No. 8, 50 parts of talc and 45 parts of kaolin were uniformly mixed to form dusts.

Formulation 2. Wattable powders

Fifty parts of the compound having compound No. 20, 29 parts of clay, 10 parts of diatomaceous earth, 5 parts of white carbon, 3 parts of sodium lignosulfonate, 2 parts of "Newcol" 1106 (trade name, Nihon Nyukazai K. K. Japan) and 1 part of polyvinyl alcohol were uniformly mixed in a mixer and pulverized three times by a hammer mill to give wettable powders.

Formulation 3. Granules

Seventy parts of the compound having compound No. 32 was finely pulverized and 30 parts of clay was added thereto and then mixed in a mixer to form a premixture. 10 parts of the premix was uniformly mixed with 60 parts of clay and 30 parts of bentonite in a mixer. The mixture was kneaded with a suitable amount of water in a kneader, extruded through a screen having a diameter of 0.8 mm and dried in a draft drier at 50.degree. C. The product thus formed was adjusted by a sifter to form granules.

Experimental examples of the present fungicidal compositions thus prepared are given below. The wettable powders prepared according to the procedures in the above-mentioned Formulation 2 are used in the following experiments, each containing 50% by weight of the active compound of this invention.

Experiment 1

Test for effect against the rice blast

Rice plant seedlings, variety Nohrin No. 20, at 4 to 5 leaf stage were sprayed with each test preparation at 500 ppm in a total amount of 30 ml per 2 pots. After 3 days, the rice blast fungi were inoculated into the host plants by spraying a spore suspension of Piricularia oryzae, and the host plants were kept in a room for 48 hours under conditions at 20.degree. to 22.degree. C., 100% relative humidity. The host plants were then placed in a greenhouse at 24.degree. to 26.degree. C. and after further 3 days the number of diseased spots of the upper two leaves of the host plants was investigated. Each test was conducted at triplicate runs and the damage was indicated by the mean number of diseased spots per leaf.

The results are given in Table 1. None of the active compounds exhibited phototoxicity.

TABLE 1______________________________________ Number of Number of diseased diseasedTest compound spots per Test compound spots perNo. leaf No. leaf______________________________________4 0.0 110 1.06 0.9 111 1.09 1.0 112 0.913 0.1 121 0.720 1.1 122 1.221 0.8 135 0.942 1.0 137 0.152 1.1 141 1.455 0.9 142 1.157 1.2 144 1.368 0.0 159 0.093 1.0 160 0.894 1.1 173 0.096 1.3 179 1.298 1.0 204 1.1102 1.1 222 1.2 (hydro-103 0.9 chloride)109 1.5______________________________________

Experiment 2

Test for effect against the brown spot of rice plants

Following the procedures of Experiment 1, but using a spore suspension of Cochliobolus miyabeanus and test preparations at 500 ppm, the effect against the brown spot was tested. Each test was conducted at triplicate runs and the damage was indicated by the mean number of diseased spots per leaf. The results are given in Table 2. None of the active compounds exhibited any phytotoxicity.

TABLE 2______________________________________ Number of diseased spotsTest compound No. per leaf______________________________________2 0.04 2.06 0.0135 0.0222 3.2(hydrochloride)______________________________________

Experiment 3

Test for effect against the bacterial leaf blight of rice plants

Groups of rice plants, variety Kimmaze, were planted in a series of Wager pots having a surface area of 1/5000 are and grown to the flag leaf stage. Each rice plant was inoculated with a suspension of pathogenic microorganism Xanthomonas oryzae by spraying and then kept for 1 day in a room at 26.degree. to 28.degree. C., 100% relative humidity. The pots were placed in a greenhouse at 28.degree. C. Three days after the inoculation, each pot was treated with 20 ml of an aqueous suspension containing 1000 ppm of one of the active compounds shown in Table 3, applied to the host plants by spraying over their stems and leaves. 20 days after the application of the active compounds, the diseased area percentage of the flag and second leaves was measured. Three pots were used for each test. The results are given in Table 3. Compounds No. 43 and No. 55 showed slight phytotoxicity.

TABLE 3______________________________________Test compound Diseased area Test compound Diseased areaNo. (%) No. (%)______________________________________3 17 95 1410 15 102 1811 5 106 012 21 107 013 9 109 1318 10 111 720 8 121 324 12 136 040 0 139 642 10 140 1143 14 147 752 6 153 1354 9 162 055 15 171 457 9 172 765 10 173 1679 20 175 884 15 179 587 12 204 1488 0 206 1193 9 285 10______________________________________

EXPERIMENT 4

Test for effect against the late blight of tomatoes

Groups of tomatoes, variety Shinfukuju, at the 5 to 6 leaf stage were sprayed with 20 ml per pot of an aqueous suspension containing 500 ppm of one of the active compounds shown in Table 4. After air-drying, each plant was inoculated with a spore suspension of pathogenic microorganism Phytophthora infestans by spraying and kept for 24 hours in a wet room at 20.degree. C. and more than 95% humidity. The pots were then kept in a greenhouse at 25.degree. C., and after 5 days, the diseased area of the upper three leaves of each plant was measured. Two pots were used for each test and the average diseased area per leaf was calculated. The results are given in Table 4. None of the active compounds exhibited any phytotoxicity.

TABLE 4______________________________________ Dis- Dis- Dis-Test eased Test eased Test easedcompound area compound area compound areaNo. (%) No. (%) No. (%)______________________________________3 15 102 0 172 24 0 103 0 173 08 9 105 28 174 09 10 106 0 175 010 2613 014 11 107 0 179 1620 2 109 0 195 021 16 110 0 197 122 15 111 0 198 023 15 112 0 199 024 0 113 0 200 027 3 114 2 201 028 4 115 0 202 230 2 117 0 204 031 0 118 0 206 233 15 121 0 222 034 34 122 4 223 1637 17 124 0 225 740 0 125 7 226 1341 5 126 0 229 342 20 127 4 232 543 24 128 0 235 046 1 129 0 248 148 0 137 18 261 051 0 139 4 285 855 9 140 18 286 1256 16 141 22 287 457 27 142 23 291 1059 0 144 11 292 962 0 151 28 294 1664 5 152 13 295 565 3 153 1673 3 154 576 23 155 079 21 157 084 0 158 1587 0 159 0 164 27 170 0______________________________________

EXPERIMENT 5

Test for effect against the early blight of tomatoes

Groups of two tomato plants, variety Shinfukuju, were planted in a series of Wager pots having a diameter of 12 cm and used as host plants when at the 5 to 6 leaf stage. Each pot was treated with 30 ml of an aqueous suspension containing 500 ppm of one of the active compounds shown in Table 5, applied to the host plants by spraying over their stems and leaves. After air-drying, each plant was inoculated with a spore suspension of the pathogenic microorganism Alternalia solani and kept in a wet room for 24 hours at 20.degree.-22.degree. C., 100% relative humidity. The pots were then placed in a greenhouse for 3 days. The presence of the disease of all leaves was investigated and the number of disease spot per leaf was calculated, using three pots for each test. The results are given in Table 5. None of the active compounds exhibited any phytotoxicity.

TABLE 5______________________________________Test Number of Test Number ofcompound diseased spots compound diseased spotsNo per leaf No. per leaf______________________________________6 16 125 314 0 127 620 0 131 721 37 142 2530 5 144 2032 25 151 1939 9 152 342 10 153 247 0 157 049 0 158 1453 20 159 055 32 160 065 2 170 1668 0 172 071 6 173 2073 12 175 087 25 177 094 49 183 496 13 195 097 0 197 1498 0 198 0102 0 200 27103 29 202 10104 0 204 0106 14 206 0109 18 222110 0 (hydrochloride) 0111 7 223 10113 6 225 18117 12 232 9118 34 235 0120 27 285 7122 16 286 7124 23 287 7 291 3 295 7______________________________________

EXPERIMENT 6

Test for effect against the anthracnose of cucumbers

Groups of two cucumber plants, variety Sagamihanshiro, were planted in a series of Wagner pots having a diameter of 12 cm and used as host plants when the first leaf was fully grown and open. Each test group of three pots was treated with one of the active compounds shown in Table 6, by spraying on an aqueous suspension containing 500 ppm of the active compound at the rate of 30 ml per 3 pots. After air-drying, the host plants were inoculated by spraying with a spore suspension of the pathogenic microorganism Colletotrichum lagenarium and kept in a wet room for 24 hours at 20.degree. to 22.degree. C., 100% relative humidity. The pots were then placed in a greenhouse at 26.degree. C., and seven days after the inoculation, the diseased area percentage of the cotyledon and the first leaf was calculated. The results are given in Table 6.

None of the active compounds exhibited any phytotoxicity.

TABLE 6______________________________________ Dis- Dis- Dis-Test eased Test eased Test easedcompound area compound area compound areaNo. (%) No. (%) No. (%)______________________________________2 14 103 0 158 164 6 106 0 159 06 0 107 0 170 08 0 109 0 172 013 0 110 0 173 020 5 112 3 174 023 0 113 0 175 2128 2 114 0 179 230 035 0 117 5 197 039 11 118 0 200 241 0 119 13 201 042 20 122 0 204 146 5 124 0 222 047 13 125 0 223 348 0 126 0 225 1051 0 127 4 226 055 8 128 6 229 557 17 129 0 232 3159 12 136 19 234 062 0 137 0 248 1265 0 141 0 261 768 0 142 15 285 1170 0 144 0 286 279 0 147 12 287 084 12 152 9 288 285 8 153 9 290 0102 0 155 6 291 0 295 2______________________________________

EXPERIMENT 7

Test for effect against the powdery mildew of cucumbers

Cucumber seedlings, variety Sagamihanshiro, planted two per 12 cm diameter pot, were used as host plants at the stage when the first leaf was fully grown and open. Each test group of three pots was treated with one of the active compounds shown in Table 7, by spraying on an aqueous suspension containing 500 ppm of the active compound at the rate of 20 ml per 3 pots. After air-drying, the host plants were inoculated with Sphaerotheca fuliginea by brushing already infected cucumber leaves with a small brush and letting the microorganism fall onto the host plants. The inoculated plants were kept in a greenhouse at 24.degree. to 26.degree. C. for 10 days, and at the end of this period the diseased area percentage was measured. Three pots were used for each test. The results are given in Table 7. None of the active compounds exhibited any phytotoxicity.

TABLE 7______________________________________ Dis- Dis- Dis-Test eased Test eased Test easedcompound area compound area compound areaNo. (%) No. (%) No. (%)______________________________________6 18 70 5 147 88 0 71 13 154 813 0 79 2 163 1314 3 84 0 170 720 0 85 0 171 1023 7 102 5 173 024 30 103 19 174 027 0 106 0 175 1528 2 107 0 179 330 0 110 8 195 431 0 111 13 197 335 0 113 4 204 737 3 114 0 206 039 6 118 28 222 0 (hydro-40 9 120 20 chloride)41 0 124 4 225 043 0 126 18 226 346 0 127 8 232 047 11 128 18 234 055 256 457 17 129 7 248 859 23 135 0 261 562 0 137 0 286 064 10 141 10 287 1065 0 142 12 288 667 5 144 12 290 3 295 3______________________________________

EXPERIMENT 8

Test for repellent action against the fourth instar larva of cabbage armyworms

Cabbage leaves were dipped for 30 seconds in an aqueous suspension containing 1000 ppm or 100 ppm of one of the active compounds shown in Table 8. After air-drying, the leaves were placed on vermiculite in a plastic receptacle of 15 cm.times.20 cm, and five per receptacle of the fourth instar larvae of cabbage armyworm were released on the leaves, while other leaves without dipping being placed 12 cm away from the dipped leaves in the receptacle.

After 24 hours, the extent of ingestion of the dipped and non-dipped leaves was measured, using two receptacles for each test.

The results are given in Table 8.

TABLE 8______________________________________ Extent of ingestionTest compound 1000 ppm 100 ppmNo. Dipped Non-dipped Dipped Non-dipped______________________________________ 8 -- +++ .+-. +++41 -- +++ .+-. +++Control (None) +++ +++______________________________________

EXPERIMENT 9

Test for repellent action against the third instar larva of tobacco cutworm

Cabbage leaves were dipped for 30 seconds in an aqueous suspension containing 1000 ppm or 100 ppm of one of the active compounds shown in Table 9. After air-drying, the leaves were placed in a plastic receptacle having a diameter of 8 cm, and 10 per receptacle of the third instar larvae of tobacco cutworm were released on the leaves. After 72 hours, the extent of ingestion of the leaves was measured, using two receptacles for each test. The results are given in Table 9.

TABLE 9______________________________________Test compound Extent of ingestionNo. 1000 ppm 100 ppm______________________________________ 62 - -102 .+-. +113 - .+-.118 .+-. +126 - .+-.128 - .+-.Control (None) +++ +++______________________________________

Claims

1. A compound having the formula ##STR3## wherein: A and B each represents a hydrogen atom;

X represents an alkylene group;

Y represents an oxygen atom or a sulfur atom; and

Z represents an unsubstituted phenyl group or a phenyl group substituted with 1 to 3 substituents which are the same or different and selected from the group consisting of a lower alkyl group, a lower alkoxy group, a lower alkylthio group, a phenyl group, a trifluoromethyl group and a halogen atom; or a salt thereof.

2. The compound of claim 1 wherein X is ethylene.

3. The compound of claim 1 wherein Y is oxygen.

4. The compound of claim 1 wherein X is ethylene and Y is oxygen.

5. The compound of claim 1 wherein X is a straight or branched chain alkylene group having 2 to 8 carbon atoms.

6. The compound of claim 1 wherein Z is an unsubstituted phenyl group or a phenyl group substituted with 1 to 3 substituents which are the same or different and are selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, a phenyl group, a trifluoromethyl group and a halogen atom.

7. The compound of claim 1 wherein Z is a phenyl group substituted with 1 to 3 substituents selected from the group consisting of methyl group, methoxy group, methylthio group, trifluoromethyl group and chlorine.

8. The compound of any one of claims 2, 3 or 4 wherein Z is a phenyl group substituted with an alkyl group having 1 to 4 carbon atoms at the 2-position.

9. The compound of any one of claims 2, 3 or 4 wherein Z is a phenyl group substituted with 1 to 3 substituents which are the same or different and are selected from the group consisting of alkyls having 1 to 4 carbon atoms.

10. The compound of claim 9 wherein at least one of said alkyl groups is methyl.

11. The compound of claim 9 wherein said phenyl group is substituted with a substituent at the 2-position and at the 4-position, and wherein the substituent at the 2-position is the methyl group.

12. The compound of claim 1 which is 4-[2-(2-methylphenoxy)ethyl]aminoquinazoline.

13. The compound of claim 1 which is 4-[2-(2-isopropylphenoxy)ethyl]aminoquinazoline.

14. The compound of claim 1 which is 4-[2-(2,4-dimethylphenoxy)ethyl]aminoquinazoline.

15. The compound of claim 1 which is 4-[2-(2-methyl-4-chlorophenoxy)ethyl]aminoquinazoline.