Herbicides

Abstract

Herbicides containing thiocarbamate derivatives represented by the general formula (I) as an active ingredient ##STR1## wherein X is 5-indanyl, 5,6,7,8-tetrahydro-2-naphthyl, 1,4-methano-1,2,3,4-tetrahydro-6-naphthyl, 1,4-ethano-1,2,3,4-tetrahydro-6-naphthyl, or substituted phenyl,Y is lower alkyl,Z is naphthyl which is unsubstituted or phenyl which is unsubstituted or substituted.

Description

DETAILED EXPLANATION OF THE INVENTION

The present invention concerns herbicides comprising thiocarbamate derivatives as an active ingredient.

Hitherto, it has been well-known that O-aryl N-arylthiocarbamate derivatives have antifungal activity and nematocidal activity as drugs and also that carbamate, thiolcarbamate and dithiocarbamate derivatives generally have herbicidal activity. For example, there is a description in Japanese unexamined patent publication No. 49925/1973 that some aryl N-arylcarbamate derivatives can be used as herbicides. However, it has been unknown that O-aryl N-arylthiocarbamate derivatives can be used as effective herbicides.

The present inventors have earnestly conducted an investigation to develop herbicides containing O-aryl N-arylthiocarbamate derivatives which exhibit sufficient herbicidal activity and high selectivity.

More especially, the present invention provides herbicides containing O-aryl N-arylthiocarbamate derivatives represented by the general formula (I) as an active ingredient (hereinafter referred to as the herbicides of the present invention) ##STR2## wherein X is 5-indanyl, 5,6,7,8-tetrahydro-2-naphthyl, 1,4-methano-1,2,3,4-tetrahydro-6-naphthyl, 1,4-ethano-1,2,3,4-tetrahydro-6-naphthyl, or substituted phenyl having one or two of the same or different substituents selected from the group of halogeno, lower alkyl, lower alkoxy, lower alkenyloxy, lower alkynyloxy, lower alkylthio, acyl, nitro, cyano, methylenedioxy, and trifluoromethyl,

Y is lower alkyl, Z is naphthyl which is unsubstituted or phenyl which is unsubstituted or substituted by one or two of the same or different substituents selected from the group of halogeno, lower alkyl, lower alkoxy, lower alkylamino, trifluoromethyl, and fluorinated lower alkoxy.

The herbicides of the present invention show extremely excellent herbicidal activity against barnyard grass as well as many general weeds in the paddy field, and they are substantially harmless against transplanted rice plants. Therefore, these herbicides are suitable for use in the paddy field. In addition, the herbicides of the present invention were recognized to have an applicability to be used in the farmland from the observation that they showed excellent herbicidal selectivity between gramineous weeds and broadleaved crops in the soil treatment of the farmland.

Thiocarbamate derivatives represented by the general formula (I), an active ingredient of the herbicides of the present invention, can be prepared according to the following reaction equations (1) and (2) ##STR3## wherein X is 5-indanyl, 5,6,7,8-tetrahydro-2-naphthyl, 1,4-methano-1,2,3,4-tetrahydro-6-naphthyl, 1,4-ethano-1,2,3,4-tetrahydro-6-naphthyl, or substituted phenyl having one or two of the same or different substituents selected from the group of halogen, lower alkyl, lower alkoxy, lower alkenyloxy, lower alkynyloxy, lower alkylthio, acyl, nitro, cyano, methylenedioxy, and trifluoromethyl,

Y is lower alkyl, Z is naphthyl which is unsubstituted or phenyl which is unsubstituted or substituted by one or two of the same or different substituents selected from the group of halogeno, lower alkyl, lower alkoy, lower alkylamino, trifluoromethyl, and fluorinated lower alkoxy, Hal is a halogen atom.

The above-stated reactions proceed in the presence of dehydrohalogenation agents and further in the presence or absence of reaction solvents usually at the reaction temperature ranging from 0.degree. to 150.degree. C. during the reaction time ranging from about few minutes to 48 hours.

As the dehydrohalogenation agents, alkali hydroxides such as sodium hydroxide, potassium hydroxide and the like; alkali earth hydroxides such as calcium hydroxide and the like; alkali carbonates such as sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate and the like; metal hydrides such as sodium hydride and the like; and tertiary amines such as triethylamine, N,N-dimethylaniline, pyridine and the like can be exemplified. The starting amine derivatives can be used as the dehydrohalogenation agents in the reaction shown by the equation (2).

As the reaction solvents, water; alcohols such as methanol, ethanol, isopropanol and the like; ketones such as acetone, methyl ethyl ketone and the like; aromatic hydrocarbons such as benzene, toluene, xylene, and the like; ethers such as ethyl ether, tetrahydrofuran, dioxane and the like; halogenated hydrocarbons such as chlorobenzene, chloroform, carbon tetrachloride, dichloroethane and the like; and polar solvents such as dimethylformamide, dimethylsulfoxide and the like can be used.

Typical example of thiocarbamate derivatives represented by the general formula (I) having number for an identification with those properties are shown herein-below.

__________________________________________________________________________NO. NAME OF THE THIOCARBAMATE DERIVATIVES AND THEIR PROPERTIES__________________________________________________________________________1. 0-5,6,7,8-Tetrahydro-2-naphthyl N--methyl-N--(3-methylphenyl)thiocarba mate mp 51-54.degree. C.2. 0-5-Indanyl N--methyl-N--(3-methylphenyl)thiocarbamate mp 97-99.degree. C.3. 0-1,4-Methano-1,2,3,4-tetrahydro-6-naphthyl N--methyl-N--(3-methylphen yl)thiocarbamate mp 93.5-97.degree. C.4. 0-5-Indanyl N--methyl-N--phenylthiocarbamate mp 88.5-90.degree. C.5. 0-5,6,7,8-Tetrahydro-2-naphthyl N--methyl-N--phenylthiocarbamate mp 79-80.degree. C.6. 0-5-Indanyl N--methyl-N--(2-methylphenyl)thiocarbamate mp 84-85.5.degree. C.7. 0-5,6,7,8-Tetrahydro-2-naphthyl N--methyl-N--(2-methylphenyl)thiocarba mate mp 74.5-76.degree. C.8. 0-5-Indanyl N--methyl-N--(4-methylphenyl)thiocarbamate mp 66-68.5.degree. C.9. 0-5,6,7,8-Tetrahydro-2-naphthyl N--methyl-N--(4-methylphenyl)thiocarba mate mp 92.5-94.degree. C.10. 0-5-Indanyl N--(2-ethylphenyl)-N--methylthiocarbamate oil11. 0-5,6,7,8-Tetrahydro-2-naphthyl N--(2-ethylphenyl)-N--methylthiocarbam ate mp 63.5-65.degree. C.12. 0-5-Indanyl N--(3-ethylphenyl)-N--methylthiocarbamate mp 68-69.degree. C.13. 0-5,6,7,8-Tetrahydro-2-naphthyl N--(3-ethylphenyl)-N--methylthiocarbam ate mp 48-49.degree. C.14. 0-5-Indanyl N--(4-ethylphenyl)-N--methylthiocarbamate oil15. 0-5,6,7,8-Tetrahydro-2-naphthyl N--(4-ethylphenyl)-N--methylthiocarbam ate mp 76.5-78.5.degree. C.16. 0-5-Indanyl N--(2-fluorophenyl)-N--methylthiocarbamate mp 105.5-108.degree. C.17. 0-5,6,7,8-Tetrahydro-2-naphthyl N--(2-fluorophenyl)-N--methylthiocarba mate mp 60.5-62.degree. C.18. 0-5-Indanyl N-- (3-fluorophenyl)-N--methylthiocarbamate mp 100-101.5.degree. C.19. 0-5,6,7,8-Tetrahydro-2-naphthyl N--(3-fluorophenyl)-N--methylthiocarba mate mp 101-102.5.degree. C.20. 0-5-Indanyl N--(4-fluorophenyl)-N--methylthiocarbamate mp 82-84.degree. C.21. 0-5,6,7,8-Tetrahydro-2-naphthyl N--(4-fluorophenyl)-N--methylthiocarba mate mp 66-67.degree. C.22. 0-5-Indanyl N--(2-chlorophenyl)-N--methylthiocarbamate mp 98-100.degree. C.23. 0-5,6,7,8-Tetrahydro-2-naphthyl N--(2-chlorophenyl)-N--methylthiocarba mate mp 73-75.degree. C.24. 0-5-Indanyl N--(3-chlorophenyl)-N--methylthiocarbamate mp 121-122.degree. C.25. 0-5,6,7,8-Tetrahydro-2-naphthyl N--(3-chlorophenyl)-N--methylthiocarba mate mp 86-87.degree. C.26. 0-5-Indanyl N--(4-chlorophenyl)-N--methylthiocarbamate mp 108-109.degree. C.27. 0-5,6,7,8-Tetrahydro-2-naphthyl N--(4-chlorophenyl)-N--methylthiocarba mate mp 77-78.5.degree. C.28. 0-5-Indanyl N--(2-bromophenyl)-N--methylthiocarbamate mp 86-89.degree. C.29. 0-5,6,7,8-Tetrahydro-2-naphthyl N--(2-bromophenyl)-N--methylthiocarbam ate mp 94-96.degree. C.30. 0-5-Indanyl N--(3-bromophenyl)-N--methylthiocarbamate mp 122.5-125.degree. C.31. 0-5,6,7,8-Tetrahydro-2-naphthyl N--(3-bromophenyl)-N--methylthiocarbam ate mp 81.5-83.degree. C.32. 0-5-Indanyl N--(2-methoxyphenyl)-N--methylthiocarbamate mp 105-105.5.degree. C.33. 0-5,6,7,8-Tetrahydro-2-naphthyl N--(2-methoxyphenyl)-N--methylthiocarb amate oil34. 0-5-Indanyl N--(3-methoxyphenyl)-N--methylthiocarbamate mp 89-90.5.degree. C.35. 0-5,6,7,8-Tetrahydro-2-naphthyl N--(3-methoxyphenyl)-N--methylthiocarb amate mp 88-88.5.degree. C.36. 0-5,6,7,8-Tetrahydro-2-naphthyl N--(4-methoxyphenyl)-N--methylthiocarb amate mp 92-93.5.degree. C.37. 0-5-Indanyl N--(3-trifluoromethylphenyl)-N--methylthiocarbamate mp 102.5-104.degree. C.38. 0-5-Indanyl N--methyl-N--(2,3-dimethylphenyl)thiocarbamate mp 118-119.5.degree. C.39. 0-5,6,7,8-Tetrahydro-2-naphthyl N--methyl-N--(2,3-dimethylphenyl)thioc arbamate mp 98.5-100.degree. C.40. 0-5-Indanyl N--methyl-N--(2,4-dimethylphenyl)thiocarbamate mp 79-80.degree. C.41. 0-5,6,7,8-Tetrahydro-2-naphthyl N--methyl-N--(2,4-dimethylphenyl)thioc arbamate mp 59-62.degree. C.42. 0-5-Indanyl N--methyl-N--(2,5-dimethylphenyl)thiocarbamate mp 141-144.degree. C.43. 0-5,6,7,8-Tetrahydro-2-naphthyl N--methyl-N--(2,5-dimethylphenyl)thioc arbamate mp 107-109.5.degree. C.44. 0-5-Indanyl N--methyl-N--(3,4-dimethylphenyl)thiocarbamate mp 112-113.5.degree. C.45. 0-5,6,7,8-Tetrahydro-2-naphthyl N--methyl-N--(3,4-dimethylphenyl)thioc arbamate mp 72-74.degree. C.46. 0-5-Indanyl N--methyl-N--(3,5-dimethylphenyl)thiocarbamate mp 162-165.degree. C.47. 0-5,6,7,8-Tetrahydro-2-naphthyl N--methyl-N--(3,5-dimethylphenyl)thioc arbamate mp 111-113.degree. C.48. 0-5-Indanyl N--(3-chloro-2-methylphenyl)-N--methylthiocarbamate mp 104-106.5.degree. C.49. 0-5,6,7,8-Tetrahydro-2-naphthyl N--(3-chloro-2-methylphenyl)-N--methyl thiocarbamate mp 104.5-106.degree. C.50. 0-5-Indanyl N--(3-chloro-4-methylphenyl)-N--methylthiocarbamate mp 106-107.degree. C.51. 0-5,6,7,8-Tetrahydro-2-naphthyl N--(3-chloro-4-methylphenyl)-N--methyl thiocarbamate mp 81.5-83.degree. C.52. 0-5-Indanyl N--(5-chloro-2-methoxyphenyl)-N--methylthiocarbamate mp 152.5-154.5.degree. C.53. 0-5,6,7,8-Tetrahydro-2-naphthyl N--(5-chloro-2-methoxyphenyl)-N--methy lthiocarbamate mp 133.5-134.5.degree. C.54. 0-5-Indanyl N--(3-methoxy-4-methylphenyl)-N--methylthiocarbamate mp 96.5-97.5.degree. C.55. 0-5,6,7,8-Tetrahydro-2-naphthyl N--(3-methoxy-4-methylphenyl)-N--methy lthiocarbamate mp 78-79.5.degree. C.56. 0-5-Indanyl N--(3,4-dimethoxyphenyl)-N--methylthiocarbamate mp 159-161.degree. C.57. 0-5,6,7,8-Tetrahydro-2-naphthyl N--(3,4-dimethoxyphenyl)-N--methylthio carbamate mp 137.5-138.5.degree. C.58. 0-5-Indanyl N--(3,4-dichlorophenyl)-N--methylthiocarbamate mp 135-136.degree. C.59. 0-5,6,7,8-Tetrahydro-2-naphthyl N--(3,4-dichlorophenyl)-N--methylthioc arbamate mp 103-104.degree. C.60. 0-5-Indanyl N--methyl-N--(1-naphthyl)thiocarbamate mp 138-140.5.degree. C.61. 0-3-tert-Butylphenyl N--methyl-N--(3-methylphenyl)thiocarbamate mp 62-63.5.degree. C.62. 0-4-tert-Butylphenyl N--methyl-N--(3-methylphenyl)thiocarbamate mp 104-105.degree. C.63. 0-3,4-Dimethylphenyl N--methyl-N--(3-methylphenyl)thiocarbamate mp 82.5-83.5.degree. C.64. 0-4-tert-Butylphenyl N--(3-methoxyphenyl)-N--methylthiocarbamate mp 88-89.degree. C.65. 0-4-tert-Butylphenyl N--(3-chlorophenyl)-N--methylthiocarbamate mp 89-92.degree. C.66. 0-4-tert-Butylphenyl N--(3,4-dichlorophenyl)-N--methylthiocarbamate mp 108-109.degree. C.67. 0-4-Methylphenyl N--methyl-N--(3-methylphenyl)thiocarbamate mp 62-63.degree. C.68. 0-4-Ethylphenyl N--methyl-N--(3-methylphenyl)thiocarbamate oil69. 0-4-Isopropylphenyl N--methyl-N--(3-methylphenyl)thiocarbamate mp 76.5-77.degree. C.70. 0-4-sec-Butylphenyl N--methyl-N--(3-methylphenyl)thiocarbamate mp 59-61.degree. C.71. 0-4-tert-Pentylphenyl N--methyl-N--(3-methylphenyl)thiocarbamate mp 87-88.5.degree. C.72. 0-4-tert-Butylphenyl N--methyl-N--phenylthiocarbamate mp 144.5-146.degree. C.73. 0-4-tert-Butylphenyl N--methyl-N--(2-methylphenyl)thiocarbamate mp 111-112.degree. C.74. 0-4-tert-Butylphenyl N--methyl-N--(4-methylphenyl)thiocarbamate mp 146.5-148.degree. C.75. 0-4-tert-Butylphenyl N--(3-ethylphenyl)-N--methylthiocarbamate mp 49.5-51.5.degree. C.76. 0-4-tert-Butylphenyl N--(2-fluorophenyl)-N--methylthiocarbamate mp 142-143.degree. C.77. 0-4-tert-Butylphenyl N--(3-fluorophenyl)-N--methylthiocarbamate mp 137.5-138.5.degree. C.78. 0-4-tert-Butylphenyl N--(4-fluorophenyl)-N--methylthiocarbamate mp 123-124.5.degree. C.79. 0-4-tert-Butylphenyl N--(2-chlorophenyl)-N--methylthiocarbamate mp 107.5-108.5.degree. C.80. 0-4-tert-Butylphenyl N--(4-chlorophenyl)-N--methylthiocarbamate mp 159-160.5.degree. C.81. 0-4-tert-Butylphenyl N--(3-bromophenyl)-N--methylthiocarbamate mp 70-71.5.degree. C.82. 0-4-tert-Butylphenyl N--(2-methoxyphenyl)-N--methylthiocarbamate mp 112-114.degree. C.83. 0-4-tert-Butylphenyl N--(3-trifluoromethylphenyl)-N--methylthiocarbama te mp 54-55.degree. C.84. 0-4-tert-Butylphenyl N--methyl-N--(3,4-dimethylphenyl)thiocarbamate mp 115.5-117.degree. C.85. 0-4-tert-Butylphenyl N--methyl-N--(3,5-dimethylphenyl)thiocarbamate mp 97-98.5.degree. C.86. 0-4-tert-Butylphenyl N--(3-chloro-4-methylphenyl)-N--methylthiocarbama te mp 104.5-106.degree. C.87. 0-4-tert-Butylphenyl N--(3-methoxy-4-methylphenyl)-N--methylthiocarbam ate mp 113.5-114.5.degree. C.88. 0-4-tert-Butylphenyl N--methyl-N--(1-naphthyl)thiocarbamate mp 107-108.degree. C.89. 0-4-tert-Pentylphenyl N--(3-methoxyphenyl)-N--methylthiocarbamate mp 59-61.degree. C.90. 0-4-Methoxyphenyl N--methyl-N--(3-methylphenyl)thiocarbamate mp 94-95.degree. C.91. 0-4-Butoxyphenyl N--methyl-N--(3-methylphenyl)thiocarbamate oil92. 0- 1,4-Ethano-1,2,3,4-tetrahydro-6-naphthyl N--methyl-N--(3-methylphen yl)thiocarbamate mp 110-112.degree. C.93. 0-3-tert-Butylphenyl N--(3-methoxyphenyl)-N--methylthiocarbamate mp 64-65.degree. C.94. 0-4-Butylphenyl N--methyl-N--(3-methylphenyl)thiocarbamate oil95. 0-4-Isopropylphenyl N--(3-methoxyphenyl)-N--methylthiocarbamate mp 51-53.5.degree. C.96. 0-4-sec-Butylphenyl N--(3-methoxyphenyl)-N--methylthiocarbamate oil97. 0-4-Isopropylphenyl N--methyl-N--phenylthiocarbamate mp 87-88.degree. C.98. 0-3-tert-Butylphenyl N--methyl-N--phenylthiocarbamate mp 78.5-79.degree. C.99. 0-3-tert-Butylphenyl N--methyl-N--(2-methylphenyl)thiocarbamate mp 98.5-99.5.degree. C.100. 0-3-tert-Butylphenyl N--methyl-N--(4-methylphenyl)thiocarbamate mp 80.5-81.5.degree. C.101. 0-3-tert-Butylphenyl N--(2-fluorophenyl)-N--methylthiocarbamate mp 79.5-81.degree. C.102. 0-3-tert-Butylphenyl N--(3-fluorophenyl)-N--methylthiocarbamate mp 75-77.degree. C.103. 0-3-tert-Butylphenyl N--(4-fluorophenyl)-N--methylthiocarbamate oil104. 0-3-tert-Butylphenyl N--(3-bromophenyl)-N--methylthiocarbamate mp 84-86.degree. C.105. 0-3-tert-Butylphenyl N--(3-trifluoromethylphenyl)-N--methylthiocarbama te oil106. 0-3-tert-Butylphenyl N--methyl-N--(3,4-dimethylphenyl)thiocarbamate mp 115-116.degree. C.107. 0-3-tert-Butylphenyl N--methyl-N--(3,5-dimethylphenyl)thiocarbamate mp 70-72.degree. C.108. 0-3-tert-Butylphenyl N--(3-chloro-4-methylphenyl)-N--methylthiocarbama te mp 89-90.degree. C.109. 0-3-tert-Butylphenyl N--(3-methoxy-4-methylphenyl)-N--methylthiocarbam ate oil110. 0-3-tert-Butylphenyl N--(3-ethylphenyl)-N--methylthiocarbamate mp 84.5-85.5.degree. C.111. 0-5-Isopropyl-2-methylphenyl N--methyl-N--phenylthiocarbamate oil112. 0-5-Isopropyl-2-methylphenyl N--methyl-N-- (3-methylphenyl)thiocarbam ate oil113. 0-5-Isopropyl-2-methylphenyl N--(3-methoxyphenyl)-N--methylthiocarbama te oil114. 0-3-Methylphenyl N--methyl-N--(3-methylphenyl)thiocarbamate oil115. 0-3-Ethylphenyl N--methyl-N--(3-methylphenyl)thiocarbamate oil116. 0-3-Isopropylphenyl N--methyl-N--(3-methylphenyl)thiocarbamate mp 48-49.5.degree. C.117. 0-3-tert-Butylphenyl N--(2-chlorophenyl)-N--methylthiocarbamate mp 85.5-86.5.degree. C.118. 0-3-tert-Butylphenyl N--(3-chlorophenyl)-N--methylthiocarbamate oil119. 0-3-tert-Butylphenyl N--(4-chlorophenyl)-N--methylthiocarbamate oil120. 0-3-tert-Butylphenyl N--(2-methoxyphenyl)-N--methylthiocarbamate mp 88.5-90.degree. C.121. 0-3-tert-Butylphenyl N--(4-methoxyphenyl)-N--methylthiocarbamate oil122. 0-3-tert-Butylphenyl N--(3,4-dichlorophenyl)-N--methylthiocarbamate oil123. 0-3-tert-Butylphenyl N--ethyl-N--phenylthiocarbamate oil124. 0-4-Ethyl-3-methylphenyl N--methyl-N--(3-methylphenyl)thiocarbamate oil125. 0-4-Cyanophenyl N--methyl-N--phenylthiocarbamate oil126. 0-3-Ethoxyphenyl N--(3-methoxyphenyl)-N--methylthiocarbamate mp 81.5-82.5.degree. C.127. 0-2-Chlorophenyl N--methyl-N--(3-methylphenyl)thiocarbamate oil128. 0-3-Chlorophenyl N--methyl-N--phenylthiocarbamate oil129. 0-4-Chlorophenyl N--(3-methoxyphenyl)-N--methylthiocarbamate mp 91-92.degree. C.130. 0-3-Bromophenyl N--methyl-N--(3-methylphenyl)thiocarbamate mp 72-73.degree. C.131. 0-4-Bromophenyl N--(3-methoxyphenyl)-N--methylthiocarbamate mp 104-105.degree. C.132. 0-3-Trifluoromethylphenyl N--methyl-N--(3-methylphenyl)thiocarbamate mp 86-87.degree. C.133. 0-4-Nitrophenyl N--(3-methoxyphenyl)-N--methylthiocarbamate mp 81.5-82.5.degree. C.134. 0-4-Acetylphenyl N--(3-methoxyphenyl)-N--methylthiocarbamate mp 90.5-91.5.degree. C.135. 0-4-Methylthiophenyl N--methyl-N--phenylthiocarbamate mp 90-91.degree. C.136. 0-3,4-Methylenedioxyphenyl N--methyl-N--phenylthiocarbamate mp 106.5-107.5.degree. C.137. 0-4-Chloro-3-methylphenyl N--methyl-N--phenylthiocarbamate mp 79-80.degree. C.138. 0-4-Chloro-3-methylphenyl N--methyl-N--(2-methylphenyl)thiocarbamate mp 102-103.5.degree. C.139. 0-4-Chloro-3-methylphenyl N--methyl-N--(3-methylphenyl)thiocarbamate mp 100.5-102.degree. C.140. 0-4-Chloro-3-methylphenyl N--methyl-N--(4-methylphenyl)thiocarbamate mp 67-68.degree. C.141. 0-4-Chloro-3-methylphenyl N--(3-ethylphenyl)-N--methylthiocarbamate oil142. 0-4-Chloro-3-methylphenyl N--(3-fluorophenyl)-N--methylthiocarbamate mp 104.5-106.degree. C.143. 0-4-Chloro-3-methylphenyl N--(2-chlorophenyl)-N--methylthiocarbamate mp 104-105.degree. C.144. 0-4-Chloro-3-methylphenyl N--(3-chlorophenyl)-N--methylthiocarbamate mp 104-105.degree. C.145. 0-4-Chloro-3-methylphenyl N--(4-chlorophenyl)-N--methylthiocarbamate mp 70-72.degree. C.146. 0-4-Chloro-3-methylphenyl N--(3-bromophenyl)-N--methylthiocarbamate mp 124-126.degree. C.147. 0-4-Chloro-3-methylphenyl N--(3-trifluoromethylphenyl)-N--methylthioca rbamate mp 97.5-99.degree. C.148. 0-4-Chloro-3-methylphenyl N--(3-methoxyphenyl)-N--methylthiocarbamate mp 111-113.degree. C.149. 0-4-Chloro-3-methylphenyl N--(3,4-dichlorophenyl)-N--methylthiocarbama te mp 86.5-88.degree. C.150. 0-4-Chloro-3-methylphenyl N--methyl-N--(3,4-dimethylphenyl)thiocarbama te mp 121.5-123.degree. C.151. 0-4-Chloro-3-methylphenyl N--methyl-N--(3,5-dimethylphenyl)thiocarbama te mp 118-120.degree. C.152. 0-4-Chloro-3-methylphenyl N--(3-chloro-4-methylphenyl)-N--methylthioca rbamate mp 91-93.degree. C.153. 0-4-Chloro-3-methylphenyl N--ethyl-N--phenylthiocarbamate mp 98-100.degree. C.154. 0-3-Methyl-4-methylthiophenyl N--methyl-N--(3-methylphenyl)thiocarbama te mp 100-102.degree. C.155. 0-3-Methyl-4-nitrophenyl N--methyl-N--(3-methylphenyl)thiocarbamate mp 91-93.degree. C.156. 0-4-Chloro-3-methoxyphenyl N--methyl-N--(3-methylphenyl)thiocarbamate mp 80-81.5.degree. C.157. 0-3-Allyloxy-4-chlorophenyl N--methyl-N--(3-methylphenyl)thiocarbamate S mp 69-70.5.degree. C.158. 0-4-Chloro-3-(2-propynyloxy)phenyl N--methyl-N--(3-methylphenyl)thioca rbamate oil159. 0-4-Methylthiophenyl N--(3-methoxyphenyl)-N--methylthiocarbamate mp 72-73.5.degree. C.160. 0-5,6,7,8-Tetrahydro-2-naphthyl N--(4-trifluoromethoxyphenyl)-N--methy lthiocarbamate mp 86-88.degree. C.161. 0-5,6,7,8-Tetrahydro-2-naphthyl N--[4-(1,1,2,2-tetrafluoroethoxy)pheny l]-N--methylthiocarbamate mp 78-80.5.degree. C.162. 0-3-Isopropylphenyl N--methyl-N--phenylthiocarbamate oil163. 0-3-Isopropylphenyl N--(3-methoxyphenyl)-N--methylthiocarbamate mp 60-61.degree. C.164. 0-3-Isopropylphenyl N--(3-chlorophenyl)-N--methylthiocarbamate oil165. 0-5,6,7,8-Tetrahydro-2-naphthyl N--methyl-N--(3-dimethylaminophenyl)th iocarbamate oil166. 0-5-Indanyl N--methyl-N--(3-dimethylaminophenyl)thiocarbamate mp 85.5-87.5.degree. C.167. 0-4-tert-Butylphenyl N--methyl-N--(3-dimethylaminophenyl)thiocarbamate mp 107-109.degree. C.168. 0-1,4-Methano-1,2,3,4-tetrahydro-6-naphthyl N--methyl-N--(3-dimethylam inophenyl)-thiocarbamate mp 97-98.5.degree. C.169. 0-3-tert-Butylphenyl N--methyl-N--(3-dimethylaminophenyl)thiocarbamate mp 76-77.degree. C.170. 0-4-Trifluoromethylphenyl N--methyl-N--(3-methylphenyl)thiocarbamate mp 81.5-82.5.degree. C.171. 0-4-Trifluoromethylphenyl N--(3-methoxyphenyl)-N--methylthiocarbamate mp 51-51.5.degree. C.172. 0-4-Bromo-3-methylphenyl N--methyl-N--(3-methylphenyl)thiocarbamate mp 82-84.degree. C.173. 0-4-Bromo-3-methylphenyl N--(3-methoxyphenyl)-N--methylthiocarbamate oil174. 0-3-Chloro-4-methylphenyl N--(3-methoxyphenyl)-N--methylthiocarbamate mp 82-83.degree.__________________________________________________________________________ C.

In order to use the herbicides of the present invention, proper amount of one or more than one of the thiocarbamate derivatives represented by the above-stated general formula (I) is incorporated with inert carriers to use as usual agricultural chemicals like water dispersible powder, emulsifiable concentrate, granules, dust and so on.

As solid carriers, talc, clay, diatomaceous earth, bentonite, kaoline, Japanese acid clay, white carbon, pumice powder and the like are exemplified. As liquid carriers, water, alcohol, benzene, toluene, xylene, kerosine, cyclohexane, cyclohexanone, isophorone, Butyl Cellosolve, benzyl acetate, dimethylformamide, mineral oil and the like are used.

Furthermore, surface-active agents and stabilizers can be added when they are required. In addition, the herbicides of the present invention can be applied after incorporating them with other agricultural chemicals used in the same field, for example, insecticides, fungicides, herbicides, plant growth regulators or fertilizers. Especially, there will be occasions for the herbicides of the present invention that it is proper to be mixed with other herbicides for the purpose of reducing labor for spreading or for the purpose of extending the spectrum of weed species to be effectively prevented.

As herbicides to be added, triazine herbicides such as Atrazine, Simazine, Simetryn, Prometryn and the like; carbamate herbicides such as Asulam, Benthiocarb, Molinate and the like; urea herbicides such as Linuron, Dymrone and the like; phenoxy-series herbicides such as 2,4-D, MCP, MCPB, Naproanilide and the like; diphenyl ether herbicides such as Nitrofen, Chlornitrofen, Chlomethoxynil and the like; heterocyclic-series herbicides such as Oxadiazon, Pyrazolate, Bentazon and the like; and amide herbicides such as Alachlor, Butachlor, Propanil and the like can be exemplified. It is possible to provide mixtures of the herbicides of the present invention by being skillfully combined with one or more than one of the herbicides described above to be effctive to many weed species.

Examples of the formulation to prepare the herbicides of the present invention containing the thiocarbamate derivatives represented by the above-mentioned general formula (I) are explained herein-below. In the Examples, the term "parts" means parts by weight.

EXAMPLE 1

[Water Dispersible Powder]

A mixture of the compound No. 14 (10 parts), Zeeklite (Trade Name, manufactured by Kunimine Kogyo Co., Ltd. 87.3 parts) used as the carrier material, Neopelex (Trade Name, manufactured by Kao Atlas Co., Ltd., 1.35 parts); and Solpol 800A (Trade Name, manufactured by Toho Kogyo Co., Ltd., 1.35 parts) was pulverized to give 10% water dispersible powder.

EXAMPLE 2

[Emulsifiable Concentrate]

A mixture of the compound No. 15 (25 parts) and Solpol 800A (10 parts) was dissolved in 65 parts of benzene to give 25% emulsifiable concentrate.

EXAMPLE 3

[Granules]

A mixture of the compound No. 24 (10 parts), 50 parts of bentonite, 35 parts of Kunilite (Trade Name, manufactured by Kokuho Kogyo Co., Ltd.) and 5 parts of Solpol 800A used as the surface-active agent was pulverized. After 10 parts of water was added, the mixture was kneaded to give a homogeneous mixture and then the mixture was extruded through sieving perforations having a diameter of 0.7 mm and dried. The product was cut off to give 10% granules having length of 1-2 mm.

The herbicides of the present invention do not show any phytotoxicity against many useful crops like rice, soybean, cotton and the like but have excellent herbicidal activity against various weeds. More particularly, as to the herbicidal action of the presently invented herbicides, characteristic features are that these herbicides kill weeds, or inhibit the growth, or suppress the growth considerably to result in a failure of growth competition against crops.

Application amount of the herbicides of the present invention is generally in the range of 10 to 1000 g/10 ares, preferably 50 to 500 g/10 ares as an active ingredient although it differs depending upon the place applied, the application time, the application methods, and weeds to be avoided.

The herbicides of the present invention were found to have outstanding herbicidal activity against barnyard grass as well as many weeds such as umbrella plant, monochoria, tooth cup, bulrush and so on in the use of 50-500 g/10 ares as an active ingredient, especially under submerged paddy field condition. In addition, the herbicides of the present invention are highly safe to young seedling of rice plants and no affection has been observed even in the application amount of 1000 g/10 ares as an active ingredient. Therefore, the herbicides of the present invention have extremely excellent characteristics to be used for paddy field. Furthermore, the application period can be considerably extended since some of the herbicides of the present invention have good herbicidal activity against barnyard grass even in a growth period (1- to 3-leaf stage). That is to say, it was shown that these herbicides have high applicability as soil-applied agents in a cultivation of transplanted rice plants at the primary to medium stage and immediately after flooding in a cultivation of dry-seeded rice.

Surprisingly, it was also shown that some of the herbicides of the present invention have high applicability to be used in farmland because those herbicides, when they are used as soil-applied agents after the seeding of general broadleaved crops like soybean, effectively prevent gramineous weeds such as barnyard grass, crab grass, and foxtail without any phytotoxicity to crops.

The herbicidal effects of the presently invented herbicides are explained in the below-stated Examples.

EXAMPLE 4

[Test for the Herbicidal Effects Under Submerged Conditions (1)]

Paddy field soil was charged in porcelain pots having a diameter of 9 cm, and then water was added. After the soil was tilled, weed seeds were sown on the surface of the soil and two bunches of rice plants (variety: Nihonbare) being in 2-leaf stage were transplanted in 1 cm depth. The pots were flooded to give water depth of 2 cm on the next day and predetermined amount of water dispersible powder of the herbicides of the present invention, which was dispersed in 10 ml of water, was added dropwise onto the surface of water in every pots for the treatment. Then they were settled in a greenhouse and received water in proper time intervals. After 3 weeks from the treatment with chemicals, the herbicidal effects as well as the influence against the rice plants were examined. Evaluation is expressed by 6 stage system, details of which are shown below. The obtained results are shown in Table 1.

______________________________________Ex- Phytotoxicitypression against rice plants Herbicidal effects______________________________________5 Killed 100% Prevention (Amount of residual weeds: 0%)4 Considerably 80% Prevention injured (Amount of residual weeds: 20%)3 Substantially 60% Prevention injured (Amount of residual weeds: 40%)2 A little injured 40% Prevention (Amount of residual weeds: 60%)1 Slightly injured 20% Prevention (Amount of residual weeds: 80%)0 No injured 0% Prevention (Amount of residual weeds: 100%)______________________________________ TABLE 1__________________________________________________________________________ Phytotoxicity Herbicidal effectsCompound Dose against Barnyard Umbrella ToothNo. (g/10 ares) rice plant grass plant Bulrush Monochoria cup__________________________________________________________________________1 125 0 5 5 4 5 5 250 0 5 5 5 5 5 500 0 5 5 5 5 5 1000 0 5 5 5 5 53 125 0 5 5 5 5 5 250 0 5 5 5 5 5 500 0 5 5 5 5 5 1000 0 5 5 5 5 54 125 0 5 5 4 5 5 250 0 5 5 5 5 5 500 0 5 5 5 5 5 1000 0 5 5 5 5 57 125 0 5 5 4 5 4 250 0 5 5 5 5 5 500 0 5 5 5 5 5 1000 0 5 5 5 5 59 125 0 5 5 3 5 5 250 0 5 5 4 5 5 500 0 5 5 5 5 5 1000 0 5 5 5 5 510 125 0 5 5 2 5 5 250 0 5 5 3 5 5 500 0 5 5 4 5 5 1000 0 5 5 4 5 516 125 0 5 5 4 5 5 250 0 5 5 5 5 5 500 0 5 5 5 5 5 1000 0 5 5 5 5 519 125 0 5 5 2 5 5 250 0 5 5 3 5 5 500 0 5 5 3 5 5 1000 0 5 5 4 5 521 125 0 5 5 4 5 5 250 0 5 5 5 5 5 500 0 5 5 5 5 5 1000 0 5 5 5 5 524 125 0 5 5 3 5 5 250 0 5 5 4 5 5 500 0 5 5 5 5 5 1000 0 5 5 5 5 527 125 0 5 5 2 4 4 250 0 5 5 3 5 5 500 0 5 5 4 5 5 1000 0 5 5 4 5 531 125 0 5 5 4 5 5 250 0 5 5 4 5 5 500 0 5 5 5 5 5 1000 0 5 5 5 5 533 125 0 5 5 4 5 5 250 0 5 5 5 5 5 500 0 5 5 5 5 5 1000 0 5 5 5 5 535 125 0 5 5 3 5 5 250 0 5 5 3 5 5 500 0 5 5 4 5 5 1000 0 5 5 4 5 544 125 0 5 5 1 5 5 250 0 5 5 2 5 5 500 0 5 5 3 5 5 1000 0 5 5 3 5 548 125 0 5 5 0 5 5 250 0 5 5 0 5 5 500 0 5 5 1 5 5 1000 0 5 5 2 5 551 125 0 5 5 1 5 5 250 0 5 5 1 5 5 500 0 5 5 2 5 5 1000 0 5 5 2 5 555 125 0 5 5 2 5 5 250 0 5 5 3 5 5 500 0 5 5 4 5 5 1000 0 5 5 4 5 560 125 0 3 5 0 4 4 250 0 4 5 0 4 4 500 0 4 5 1 5 5 1000 0 5 5 2 5 561 125 0 5 5 0 5 5 250 0 5 5 1 5 5 500 0 5 5 2 5 5 1000 0 5 5 3 5 562 125 0 5 5 3 5 5 250 0 5 5 4 5 5 500 0 5 5 4 5 5 1000 0 5 5 5 5 563 125 0 5 5 1 4 4 250 0 5 5 1 5 5 500 0 5 5 2 5 5 1000 0 5 5 2 5 564 125 0 5 5 1 5 5 250 0 5 5 1 5 5 500 0 5 5 2 5 5 1000 0 5 5 3 5 565 125 0 5 5 2 5 5 250 0 5 5 2 5 5 500 0 5 5 3 5 5 1000 0 5 5 4 5 567 125 0 5 5 1 4 4 250 0 5 5 1 5 5 500 0 5 5 2 5 5 1000 0 5 5 3 5 568 125 0 5 5 3 3 3 250 0 5 5 4 5 5 500 0 5 5 5 5 5 1000 0 5 5 5 5 569 125 0 5 5 1 5 5 250 0 5 5 1 5 5 500 0 5 5 2 5 5 1000 0 5 5 3 5 570 125 0 5 5 1 1 1 250 0 5 5 1 2 2 500 0 5 5 1 4 4 1000 0 5 5 2 5 571 125 0 5 5 1 5 5 250 0 5 5 3 5 5 500 0 5 5 3 5 5 1000 0 5 5 4 5 575 125 0 5 5 3 5 5 250 0 5 5 3 5 5 500 0 5 5 4 5 5 1000 0 5 5 4 5 581 125 0 5 5 1 5 5 250 0 5 5 2 5 5 500 0 5 5 2 5 5 1000 0 5 5 3 5 583 125 0 5 5 1 5 5 250 0 5 5 2 5 5 500 0 5 5 3 5 5 1000 0 5 5 4 5 586 125 0 5 5 3 5 5 250 0 5 5 4 5 5 500 0 5 5 5 5 5 1000 0 5 5 5 5 587 125 0 5 5 3 5 5 250 0 5 5 3 5 5 500 0 5 5 4 5 5 1000 0 5 5 4 5 589 125 0 5 5 4 5 5 250 0 5 5 5 5 5 500 0 5 5 5 5 5 1000 0 5 5 5 5 590 125 0 4 5 1 4 4 250 0 5 5 2 5 5 500 0 5 5 2 5 5 1000 0 5 5 3 5 592 125 0 5 5 5 5 5 250 0 5 5 5 5 5 500 0 5 5 5 5 5 1000 0 5 5 5 5 593 125 0 5 5 5 5 5 250 0 5 5 5 5 5 500 0 5 5 5 5 5 1000 0 5 5 5 5 594 125 0 4 5 1 3 3 250 0 5 5 1 4 4 500 0 5 5 2 5 5 1000 0 5 5 2 5 597 125 0 5 5 4 5 5 250 0 5 5 5 5 5 500 0 5 5 5 5 5 1000 0 5 5 5 5 598 125 0 5 5 5 5 5 250 0 5 5 5 5 5 500 0 5 5 5 5 5 1000 0 5 5 5 5 5101 125 0 5 5 0 5 5 250 0 5 5 0 5 5 500 0 5 5 1 5 5 1000 0 5 5 1 5 5105 125 0 5 5 0 4 5 250 0 5 5 1 5 5 500 0 5 5 1 5 5 1000 0 5 5 2 5 5106 125 0 5 5 0 5 5 250 0 5 5 1 5 5 500 0 5 5 1 5 5 1000 0 5 5 2 5 5107 125 0 5 5 1 5 5 250 0 5 5 2 5 5 500 0 5 5 2 5 5 1000 0 5 5 3 5 5109 125 0 5 5 1 5 5 250 0 5 5 2 5 5 500 0 5 5 3 5 5 1000 0 5 5 3 5 5113 125 0 5 5 4 5 5 250 0 5 5 4 5 5 500 0 5 5 5 5 5 1000 0 5 5 5 5 5115 125 0 5 5 3 4 3 250 0 5 5 3 5 4 500 0 5 5 5 5 5 1000 0 5 5 5 5 5116 125 0 5 5 4 4 5 250 0 5 5 5 5 5 500 0 5 5 5 5 5 1000 0 5 5 5 5 5119 125 0 5 5 3 4 4 250 0 5 5 3 4 5 500 0 5 5 4 4 5 1000 0 5 5 4 5 5123 125 0 5 5 0 4 5 250 0 5 5 0 4 5 500 0 5 5 1 5 5 1000 0 5 5 1 5 5124 125 0 5 5 5 5 5 250 0 5 5 5 5 5 500 0 5 5 5 5 5 1000 0 5 5 5 5 5125 125 0 2 3 2 3 3 250 0 3 5 3 4 3 500 0 3 5 3 4 4 1000 0 4 5 4 5 4126 125 0 3 5 0 3 2 250 0 4 5 1 4 3 500 0 4 5 1 4 4 1000 0 4 5 2 5 4129 125 0 5 5 0 3 2 250 0 5 5 0 3 3 500 0 5 5 1 4 3 1000 0 5 5 2 4 4131 125 0 4 5 0 4 1 250 0 5 5 0 4 2 500 0 5 5 1 4 2 1000 0 5 5 1 5 3133 125 0 1 4 0 1 0 250 0 2 4 0 2 1 500 0 2 5 1 3 1 1000 0 3 5 1 3 2134 125 0 1 3 0 0 0 250 0 2 4 0 0 1 500 0 3 5 1 1 1 1000 0 4 5 2 2 3135 125 0 5 5 4 4 3 250 0 5 5 4 5 4 500 0 5 5 5 5 4 1000 0 5 5 5 5 5136 125 0 2 5 2 2 2 250 0 3 5 2 3 3 500 0 4 5 3 3 3 1000 0 5 5 4 4 4137 125 0 5 5 3 5 5 250 0 5 5 4 5 5 500 0 5 5 4 5 5 1000 0 5 5 4.5 5 5140 125 0 5 5 3 5 4 250 0 5 5 3 5 4 500 0 5 5 4 5 5 1000 0 5 5 4 5 5144 125 0 5 5 3 5 4 250 0 5 5 3 5 4 500 0 5 5 4 5 4.5 1000 0 5 5 4 5 5148 125 0 5 5 1 5 2 250 0 5 5 2 5 3 500 0 5 5 2 5 4 1000 0 5 5 3 5 4149 125 0 5 5 3 5 5 250 0 5 5 4 5 5 500 0 5 5 4 5 5 1000 0 5 5 4.5 5 5152 125 0 5 5 2 5 4 250 0 5 5 2 5 4 500 0 5 5 3 5 5 1000 0 5 5 3 5 5154 125 0 5 5 3 3 5 250 0 5 5 3 3 5 500 0 5 5 4 4 5 1000 0 5 5 4 4 5155 125 0 5 5 4 5 5 250 0 5 5 4 5 5 500 0 5 5 5 5 5 1000 0 5 5 5 5 5156 125 0 5 5 4 5 4 250 0 5 5 5 5 5 500 0 5 5 5 5 5 1000 0 5 5 5 5 5157 125 0 4 5 0 3 4 250 0 5 5 0 4 5 500 0 5 5 1 4 5 1000 0 5 5 1 5 5158 125 0 5 5 4 5 5 250 0 5 5 4 5 5 500 0 5 5 5 5 5 1000 0 5 5 5 5 5160 125 0 1 3 1 2 2 250 0 2 4 2 3 3 500 0 3 5 3 5 4 1000 0 4 5 4 5 5161 125 0 3 3 2 3 1 250 0 4 4 2 4 2 500 0 4 5 3 5 3 1000 0 5 5 3 5 4163 125 0 5 5 4 5 4 250 0 5 5 4 5 5 500 0 5 5 4 5 5 1000 0 5 5 4 5 5165 125 0 5 5 2 5 4 250 0 5 5 3 5 4 500 0 5 5 3 5 5 1000 0 5 5 4 5 5167 125 0 5 5 3 5 4 250 0 5 5 3 5 5 500 0 5 5 4 5 5 1000 0 5 5 4 5 5170 125 0 5 5 3 5 4 250 0 5 5 4 5 4 500 0 5 5 4 5 5 1000 0 5 5 4 5 5171 125 0 5 5 3 5 4 250 0 5 5 4 5 4 500 0 5 5 5 5 5 1000 0 5 5 5 5 5172 125 0 5 5 4 5 4 250 0 5 5 4 5 4 500 0 5 5 5 5 5 1000 0 5 5 5 5 5173 125 0 5 5 4 5 4 250 0 5 5 4 5 5 500 0 5 5 5 5 5 1000 0 5 5 5 5 5174 125 0 5 5 3 5 3 250 0 5 5 3 5 3 500 0 5 5 4 5 3 1000 0 5 5 5 5 4Benthiocarb 125 1 5 5 2 2 3(Reference 250 2 5 5 2 2 3agent) 500 2 5 5 3 3 4 1000 3 5 5 5 4 5Not treated 0 0 0 0 0 0 0__________________________________________________________________________

EXAMPLE 5

[Test for the Herbicidal Effects Under Submerged Conditions (2)]

Paddy field soil was changed in porcelain pots having a diameter of 9 cm, and then water was added. After the soil was tilled, seeds of barnyard grass were sown on the surface of the soil and two bunches of rice plants (variety: Nihonbare) being in 2-leaf stage were transplanted in 1 cm depth. The pots were flooded to give water depth of 2 cm on the next day and predetermined amount of water dispersible powder of the herbicides of the present invention, which was dispersed in 10 ml of water, was added dropwise onto the surface of water in every pots for the treatment before the germination of and at the time of both 1.2- and 2-leaf stages of barnyard grass. The pots were settled in a greenhouse and received water in proper time intervals. The examination was carried out after 3 weeks from the treatment with the chemicals and the results were evaluated in the similar manner as in Example 4. The results are shown in Table 2.

TABLE 2__________________________________________________________________________ Herbicidal effects Phytotoxicity against barnyard grassCompound Dose against Pre- 1.2- 2-No. (g/10 ares) rice plant emergence Leaf stage Leaf stage__________________________________________________________________________1 12.5 0 5 -- 5 25 0 5 -- 5 50 0 5 -- 5 100 0 5 -- 53 12.5 0 5 -- 5 25 0 5 -- 5 50 0 5 -- 5 100 0 5 -- 535 12.5 0 5 -- 5 25 0 5 -- 5 50 0 5 -- 5 100 0 5 -- 544 12.5 0 5 -- 4 25 0 5 -- 5 50 0 5 -- 5 100 0 5 -- 562 12.5 0 5 5 -- 25 0 5 5 -- 50 0 5 5 -- 100 0 5 5 --69 12.5 0 5 4 -- 25 0 5 4 -- 50 0 5 5 -- 100 0 5 5 --72 12.5 0 5 5 -- 25 0 5 5 -- 50 0 5 5 -- 100 0 5 5 --106 12.5 0 5 -- -- 25 0 5 -- -- 50 0 5 -- -- 100 0 5 -- --116 12.5 0 5 -- -- 25 0 5 -- -- 50 0 5 -- -- 100 0 5 -- --124 12.5 0 5 -- -- 25 0 5 -- -- 50 0 5 -- -- 100 0 5 -- --137 12.5 0 3 -- -- 25 0 5 -- -- 50 0 5 -- -- 100 0 5 -- --152 12.5 0 5 -- -- 25 0 5 -- -- 50 0 5 -- -- 100 0 5 -- --Benthiocarb 12.5 0 2 1 1(Reference 25 0 3 2 2agent) 50 0 4 2.5 2.5 100 1 5 4 4Not treated 0 0 0 0 0__________________________________________________________________________

EXAMPLE 6

[Test for the Herbicidal Effects by the Surface Treatment of Farmland Soil]

Farmland soil was charged into porcelain pots having a diameter of 12 cm and several kinds of crop seeds together with weed seeds were sown. The seeds were further covered by the soil in 1 cm thickness. Predetermined amount of water dispersible powder of the herbicides of the present invention, which was dispersed in 10 ml of water per every pots, was sprayed on the surface of soil for the treatment. The pots were stationarily placed in a greenhouse and received sprayed water in proper time intervals. After 3 weeks from the treatment with the chemicals, the herbicidal effects and the influences against soybean and cotton plants were examined in the similar manner as in Example 4. The results are shown in Table 3.

TABLE 3__________________________________________________________________________ Phytotoxicity Herbicidal effectsCompound Dose Soybean Cotton Barnyard CrabNo. (g/10 ares) plant plant grass grass Foxtail__________________________________________________________________________1 100 0 0 5 5 5 200 0 0 5 5 5 400 0 0 5 5 5 800 0 0 5 5 53 100 0 0 5 5 5 200 0 0 5 5 5 400 0 0 5 5 5 800 0 0 5 5 535 100 0 0 5 5 5 200 0 0 5 5 5 400 0 0 5 5 5 800 0 0 5 5 544 100 0 0 5 5 5 200 0 0 5 5 5 400 0 0 5 5 5 800 0 0 5 5 562 50 0 0 5 5 5 100 0 0 5 5 5 200 0 0 5 5 5 400 0 0 5 5 569 50 0 0 4 4 4 100 0 0 4 5 4.5 200 0 0 5 5 5 400 0 0 5 5 572 50 0 0 5 5 5 100 0 0 5 5 5 200 0 0 5 5 5 400 0 0 5 5 598 50 0 0 5 5 5 100 0 0 5 5 5 200 0 0 5 5 5 400 0 0 5 5 5116 50 0 0 5 5 5 100 0 0 5 5 5 200 0 0 5 5 5 400 0 0 5 5 5124 50 0 0 5 5 5 100 0 0 5 5 5 200 0 0 5 5 5 400 0 0 5 5 5137 50 0 0 3 4 3 100 0 0 4 5 4 200 0 0 5 5 5 400 0 0 5 5 5152 50 0 0 5 5 5 100 0 0 5 5 5 200 0 0 5 5 5 400 0 0 5 5 5Benthiocarb 50 0 0 3 4 3(Reference 100 0 0 4 5 4agent) 200 0 0 5 5 5 400 0 0 5 5 5 800 0 0 5 5 5Not treated 0 0 0 0 0 0__________________________________________________________________________

Claims

1. A method for the control of weeds, comprising the application of a herbicidal composition containing a thiocarbamate derivative represented by the general formula (I) as an active ingredient incorporated in an inert carrier to the locus to be protected ##STR4## wherein X is 5-indanyl, 5,6,7,8-tetrahydro-2-naphthyl, 1,4-methano-1,2,3,4-tetrahydro-6-naphthyl, 1,4-ethano-1,2,3,4-tetrahydro-6-naphthyl, or substituted phenyl having one or two of the same or different substituents selected from the group consisting of halogeno, lower alkyl, lower alkoxy, lower alkenyloxy, lower alkynyloxy, lower alkylthio, acyl, nitro, cyano, methylenedioxy, and trifluoromethyl,

Y is lower alkyl,

Z is naphthyl which is unsubstituted or phenyl which is unsubstituted or substituted by one or two of the same or different substituents selected from the group consisting of halogeno, lower alkyl, lower alkoxy, lower alkylamino, trifluoromethyl, and fluorinated lower alkoxy.

2. A method for the control of weeds, comprising the application of a herbicidal composition containing a thiocarbamate derivative according to claim 1, wherein

X is 5-indanyl, 5,6,7,8-tetrahydro-2-naphthyl, 1,4-methano-1,2,3,4-tetrahydro-6-naphthyl, 1,4-ethano-1,2,3,4-tetrahydro-6-naphthyl, or substituted phenyl having one or two of the same or different substituents selected from the group consisting of a chlorine atom, a bromine atom, alkyl of 1 to 5 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkenyloxy of 3 carbon atoms, alkynyloxy of 3 carbon atoms, methylthio, acetyl, nitro, cyano, methylenedioxy, and trifluoromethyl.

3. A method for the control of weeds, comprising the application of a herbicidal composition containing a thiocarbamate derivative according to claim 1, wherein

Y is alkyl of 1 to 2 carbon atoms.

4. A method for the control of weeds, comprising the application of a herbicidal composition containing a thiocarbamate derivative according to claim 1, wherein

Z is naphthyl which is unsubstituted or or phenyl which is unsubstituted or substituted by one or two of the same or different substituents selected from the group consisting of a chlorine atom, a bromine atom, a fluorine atom, alkyl of 1 to 2 carbon atoms, methoxy, dimethylamino, trifluoromethyl, and fluorinated alkoxy of 1 to 2 carbon atoms.

5. A method for the control of weeds, comprising the application of a herbicidal composition containing a thiocarbamate derivative according to claim 1, wherein

X is 5-indanyl, 5,6,7,8-tetrahydro-2-naphthyl, 1,4-methano-1,2,3,4-tetrahydro-6-naphthyl, 1,4-ethano-1,2,3,4-tetrahydro-6-naphthyl, or substituted phenyl having one or two of the same or different substituents selected from the group consisting of a chlorine atom, a bromine atom, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkenyloxy of 3 carbon atoms, alkynyloxy of 3 carbon atoms, methylthio, acetyl, nitro, cyano, methylenedioxy, and trifluoromethyl,

Y is alkyl of 1 to 2 carbon atoms,

Z is naphthyl which is unsubstituted or phenyl which is unsubstituted or substituted by one or two of the same or different substituents selected from the group consisting of a chlorine atom, a bromine atom, a fluorine atom, alkyl of 1 to 2 carbon atoms, methoxy, dimethylamino, trifluoromethyl, and fluorinated alkoxy of 1 to 2 carbon atoms.