HERBICIDALLY ACTIVE THIOCARBAMATES AND SULFOXIDES

THIOCARBAMATES ET SULFOXYDES A PROPRIETES HERBICIDES

English Abstract

Abstract of the Disclosure
Herbicidally active S-cycloalkylmethyl
thiocarbamates and their sulfoxide derivatives
are described herein. The compounds have the
following general structural formula:
<IMG>
wherein n is 0 or 1; R is selected from the
group consisting of tertiary butyl, cyclopropyl,
cyclobutyl and cyclopentyl; and R1 and R2
are individually selected from the group
consisting of alkyl, alkenyl, cyclopropylmethyl,
cyclohexyl, phenyl and benzyl or R1 and R2
together form an alkylene group or an alkyl
substituted alkylene group.

Claims

WHAT IS CLAIMED IS:
1. A compound having the general structural formula:
<IMG>
wherein n is 0 or 1; R is selected from the group consisting of
tertiary butyl, cyclopropyl, cyclobutyl and cyclopentyl; and
R1 and R2 are individually selected from the group consisting of
alkyl, alkenyl, cyclopropylmethyl, cyclohexyl, phenyl and benzyl
or R1 and R2 together form an alkylene group or an alkyl
substituted alkylene group.
2. A compound according to Claim 1 wherein R is <IMG>,
R1 is -C2H5, R2 is -n-C4H9, and n is 0.
3. A compound according to Claim 1 wherein R is <IMG>,
R1 is -C2H5, R2 is <IMG>, and n is 0.
4. A compound according to Claim 1 wherein R is <IMG>,
R1 is -n-C3H7, R2 is -n-C3H7, and n is 0.
5. A compound according to Claim 1 wherein R is <IMG>,
R1 is -n-C4H9, R2 is <IMG>, and n is 0.
6. A compound according to Claim 1 wherein R is <IMG>,
R1 is -n-C4H9, R2 is <IMG> , and n is 0.
7. A compound according to Claim 1 wherein R is <IMG>,
R1 is -i-C4H9, R2 is -i-C4H9, and n is 0.
28

8. A compound according to Claim 1 wherein R is <IMG>,
R1 and R2 together are <IMG> and n is 0.
9. A compound according to Claim 1 wherein R is <IMG>,
R1 is -C2H5, R2 is <IMG> , and n is 0.
10. A compound acoording to Claim 1 wherein R is <IMG>,
R1 is -n-C3H7, R2 is <IMG> , and n is 0.
11. A compound according to Claim 1 wherein R is <IMG>,
R1 is -i-C3H7, R2 is <IMG> , and n is 0.
12. A compound according to Claim 1 wherein R is <IMG>,
R1 is -CH2CH=CH2, R2 is <IMG> , and n is 0.
13. A compound according to Claim 1 wherein R is <IMG>,
R1 is -s-C4H9, R2 is <IMG> , and n is 0.
14. A compound according to Claim 1 wherein R is <IMG>,
R1 is <IMG> , R2 is <IMG> , and n is 0.
15. A compound according to Claim 1 wherein R is <IMG>,
R1 is -C2H5, R2 is -CH2CH=CH2, and n is 0.
16. A compound according to Claim 1 wherein R is <IMG>,
R1 is -C2H5, R2 is <IMG> , and n is 0.
29

17. A compound according to Claim 1 wherein R is <IMG>,
R1 is -C2H5, R2 is <IMG> , and n is 0.
18. A compound according to Claim 1 wherein R is <IMG>,
R1 is -C2H5, R2 is <IMG> , and n is 0.
19. A compound according to Claim 1 wherein R is <IMG>,
R1 is -n-C3H7, R2 is i-C3H7, and n is 0.
20. A compound according to Claim 1 wherein R is <IMG>,
R1 is -s-C4H9, R2 is -s-C4H9, and n is 0.
21. A compound according to Claim 1 wherein R is <IMG>,
R1 and R2 together are <IMG> and n is 0.
22. A compound according to Claim 1 wherein R is <IMG>,
R1 is -i-C4H9, R2 is -s-C4H9, and n is 0-
23. A compound according to Claim 1 wherein R is <IMG>,
R1 is <IMG> , R2 is <IMG> , and n is 0.
24. A compound according to Claim 1 wherein R is <IMG>,
R1 and R2 together are <IMG> and n is 0.

25. A compound according to Claim 1 wherein R is <IMG>,
R1 is -n-C3H7, R2 is -n-C3H7, and n is 1.
26. A compound according to Claim 1 wherein R is <IMG>,
R1 is C2H5, R2 is -CH2CH=CH2, and n is 1.
27. A compound according to Claim 1 wherein R is <IMG>,
R1 is -C2H5, R2 is -n-C4H9, and n is 1.
28. A compound according to Claim 1 wherein R is <IMG>,
R1 is C2H5, R2 is -s-C4H9, and n is 1.
29. A compound according to Claim 1 wherein R is <IMG>,
R1 is -C2H5, R2 is <IMG> , and n is 1.
30. A compound according to Claim 1 wherein R is <IMG>,
R1 is -C2H4, R2 is <IMG> , and n is 1.
31. A compound according to Claim 1 wherein R is <IMG>,
R1 is -C2H5, R2 is <IMG> , and n is 1.
32. A compound according to Claim 1 wherein R is <IMG>,
R1 is -C2H5, R2 is <IMG> , and n is 1.
33. A compound according to Claim 1 wherein R is <IMG>,
R1 is -n-C3H7, R2 is -i-C3H7, and n is 1.
34. A compound according to Claim 1 wherein R is <IMG>,
R1 is -n-C3H7, R2 is <IMG> , and n is 1.
31

35. A compound according to Claim 1 wherein R is <IMG>,
R1 is -i-C3H7, R2 <IMG> , and n is 1.
36. A compound according to Claim 1 wherein R is <IMG>,
R1 is CH2CH=CH2, R2 is <IMG> , and n is 1.
37. A compound according to Claim 1 wherein R is <IMG>,
R1 is n C4H9, R2 is <IMG> , and n is 1.
38. A compound according to Claim 1 wherein R is <IMG>,
R1 is i-C4H9, R2 is i-C4H9, and n is 1.
39. A compound according to Claim 1 wherein R is <IMG>,
R1 is s-C4H9, R2 is s-C4H9, and n is 1.
40. A compound according to Claim 1 wherein R is <IMG>,
R1 is s-C4H9, R2 is <IMG> , and n is 1.
41. A compound according to Claim 1 wherein R is <IMG>,
R1 is <IMG> , R2 is <IMG> , and n is 1.
42. A compound according to Claim 1 wherein R is <IMG>,
R1 and R2 together are <IMG> and n is 1.
43. A compound according to Claim 1 wherein R is <IMG>,
R1 and R2 together are <IMG> and n is 1.
32

44. A compound according to Claim 1 wherein R is <IMG>,
R1 is -i-C4H9, R2 is -s-C4H9, and n is 1.
45. A compound according to Claim 1 wherein R is <IMG>,
R1 is <IMG> , R2 is <IMG> , and n is 1.
46. A compound according to Claim 1 wherein R is <IMG>,
R1 and R2 together are <IMG> , and n is 1.
47. A compound according to Claim 1 wherein R is <IMG>,
R1 is -C2H5, R2 is -n-C4H9, and n is 0.
48. A compound according to Claim 1 wherein R is <IMG>,
R1 is -C2H5, R2 is -s-C4H9, and n is 0.
49. A compound according to Claim 1 wherein R is <IMG>,
R1 is -C2H5, R2 is <IMG> , and n is 0.
50. A compound according to Claim 1 wherein R is <IMG>,
R1 is -n-C3H7, R2 is -n-C3H7, and n is 0.
51. A compound according to Claim 1 wherein R is <IMG>,
R1 is -n-C4H9, R2 is <IMG> , and n is 0.
52. A compound according to Claim 1 wherein R is <IMG>,
R1 is -i-C4H9, R2 is -i-C4H9, and n is 0.
33

53. A compound according to Claim 1 wherein R is <IMG>,
R1 is -s-C4H9, R2 is -s-C4H9, and n is 0.
54. A compound according to Claim 1 wherein R is <IMG>,
R1 is -i-C4H9, R2 is -s-C4H9, and n is 0.
55. A compound according to Claim 1 wherein R is <IMG>,
R1 and R2 together are <IMG> and n is 0.
56. A compound accordlng to Claim 1 wherein R is <IMG>,
R1 is <IMG> , R2 is <IMG> , and n is 0.
57. A compound according to Claim 1 wherein R is <IMG>,
R1 and R2 together are <IMG> , and n is 0.
58. A compound according to Claim 1 wherein R is <IMG>,
R1 and R2 together are <IMG> and n is 1.
59. A compound according to Claim 1 wherein R is <IMG>,
R1 and R2 together are <IMG> and n is 1.
34

60. A compound according to Claim 1 wherein R is <IMG>,
R1 is <IMG> , R2 is <IMG> , and n is 1.
61. A compound according to Claim 1 wherein R is <IMG>,
R1 is -C2H5, R2 is n-C4H9, and n is 0.
62. A compound according to Claim 1 wherein R is <IMG>,
R1 is -C2H5, R2 is -s-C4H9, and n is 0.
63. A compound according to Claim 1 wherein R is <IMG>,
R1 is C2H5, R2 is <IMG> , and n is 0.
64. A compound according to Claim 1 wherein R is <IMG>,
R1 is -n-C3H7, R2 i3 -n-C3H7, and n is 0.
65. A compound according to Claim 1 wherein R is <IMG>,
R1 is -i-C4H9, R2 is -i-C4H9, and n is 0.
66. A compound according to Claim 1 wherein R is <IMG>,
R1 is <IMG> , R2 is <IMG> , and n is 0.
67. A compound according to Claim 1 wherein R is <IMG>,
R1 is -i-C4H9, R2 is -s-C4H9, and n is 0.
68. A compound according to Claim 1 wherein R is <IMG>,
R1 is -s-C4H9, R2 is -s-C4H9, and n is 0.
69. A compound according to Claim 1 wherein R is <IMG>,
R1 and R2 together are <IMG> and n is 0.

70. A compound according to Claim 1 wherein R is <IMG>,
R1 is -n-C4H9, R2 is -n-C4H9, and n is 0.
71. A compound according to Claim 1 wherein R is <IMG>,
R1 and R2 together are <IMG> and n is 0.
72. A compound according to Claim 1 wherein R is
<IMG> , R1 is C2H5, R2 is n-C4H9 and n is 0.
73. A compound according to Claim 1 wherein R is
<IMG> , R1 is C2H5, R2 is i-C4H9, and n is 0.
74. A compound according to Claim 1 wherein R is
<IMG> , R1 is C2H5, R2 is sec.-C4H9, and n is 0.
75. A compound according to Claim 1 wherein R is
<IMG> , R1 is n-C3H7, R2 is n-C3H7, and n is 0.
76. A compound according to Claim 1 wherein R is
<IMG> , R1 is n-C3H7, R2 is i-C3H7, and n is 0.
36

77. A compound according to Claim 1 wherein R is
<IMG> , R1 is allyl, R2 is allyl, and n is 0.
78. A compound according to Claim 1 wherein R is
<IMG> , R1 is i-C3H7, R2 is i-C4H9, and n is 0.
79. A compound according to Claim 1 wherein R is
<IMG> , R1 is i-C4H9, R2 is i-C4H9, and n is 0.
80. A compound according to Claim 1 wherein R is
<IMG> , R, is sec.-C4H9, R2 is sec.-C4H9, and n is 0.
81. A compound according to Claim 1 wherein R is
<IMG> , R1 is i-C4H9, R2 is sec.-C4H9, and n is 0.
82. A compound according to Claim 1 wherein R is
<IMG> , R1 and R2 taken together are <IMG> , and n is
0.
37

83. A compound according to Claim 1 wherein R is
<IMG> , R1 is C2H5, R2 is allyl, and n is 0.
84. A compound according to Claim 1 wherein R is
<IMG> , R1 is C2H5, R2 is cyclohexyl, and n is 0.
85. A compound according to Claim 1 wherein R is
<IMG> , R1 is n-C4H9, R2 is cyclopropylmethyl, and n is 0.
86. A compound according to Claim 1 wherein R is
<IMG> , R1 and R2 together are <IMG> , and n is 0.
87. A compound according to Claim 1 wherein R is
<IMG> , R1 is cyclopropylmethyl, R2 is cyclopropyl methyl,
and n is 0.
88. A compound according to Claim 1 wherein R is
<IMG> , R1 and R2 taken together are <IMG> , and
38

89. A compound according to Claim 1 wherein R is
<IMG> , R1 is C2H5, R2 is sec.-C4H9, and n is 1.
90. A compound according to Claim 1 wherein R is
<IMG> , R1 is i-C4H9, R2 is sec.-C4H9, and n is 1.
91. A compound according to Claim 1 wherein R is
<IMG> , R1 is C2H5, R2 is n-C4H9, and n is 1.
92. A compound according to Claim 1 wherein R is
<IMG> , R1 is C2H5, R2 is i-C4H9, and n is 1.
93. A compound according to Claim 1 wherein R is
<IMG> , R1 is i-C3H7, R2 is i-C3H7, and n is 1.
94. A compound according to Claim 1 wherein R is
<IMG> , R1 is i-C3H7, R2 is i-C4H9, and n is 1.
39

95. A compound according to Claim 1 wherein R is
<IMG> , R1 is sec.-C4H9, R2 is sec.-C4H9, and n is 1.
96. A compound according to Claim 1 wherein R is
<IMG> , R1 is9 CH2CH=CH2, R2 is CH2CH=CH2, and n is 1.
97. A compound according to Claim 1 wherein R is
<IMG> , R1 is n-C3H7, R2 is n-C3H7, and n is 1.
98. A compound according to Claim 1 wherein R is
<IMG> , R1 is C2H5, R2 is CH2CH=CH2, and n is 1.
99. A compound according to Claim 1 wherein R is
<IMG> , R1 is C2H5, R2 is cyclohexyl, and n is 1.
100. A compound according to Claim 1 wherein R is
<IMG> , R1 is C4H9, R2 is cyclopropylmethyl, and n is 1.
101. A compound according to Claim 1 wherein R is
<IMG> , R1 and R2 taken together are <IMG>
and n is 1.

102. A compound according to Claim 1 wherein R is
<IMG> , R1 is cyclopropylmethyl, R2 is cyclopropylmethyl, and
n is 1.
103. A compound according to Claim 1 wherein R is
<IMG> , R1 is i-C4H9, R2 is i-C4H9, and n is 1.
104. A compound according to Claim 1 wherein R is
<IMG> , R1 and R2 taken together are <IMG> , and n is 0.
105. A compound according to Claim 1 wherein R is
<IMG> , R1 and R2 taken together are <IMG> , and n is 0.
106. A method of controlling undesirable vegetation which
comprises applying to the soil an effective amount of a compound
having the general structural formula
<IMG>
wherein n is 0 or 1, R is selected from the group consisting of
tertiary butyl, cyclopropyl, cyclobutyl and cyclopentyl; and
R1 and R2 are individually selected from the group consisting
of alkyl, alkenyl, cyclopropylmethyl, cyclohexyl, phenyl and
benzyl or R1 and R2 together from an alkylene group or an
alkyl substituted alkylene group.
41

107. A method according to Claim 106 wherein R is <IMG>,
R1 is -C2H5, R2 is -s-C4H9, and n is 0.
108. A method according to Claim 106 wherein R is <IMG>,
R1 is -n-C3H7, R2 is -n-C3H7, and n is 0.
109. A method according to claim 105 wherein R is <IMG>,
R1 is -n-C4H9, R2 is -n-C4H9, and n is 0.
110. A method according to Claim 106 wherein R is <IMG>,
R1 is -n-C4H9, R2 is <IMG> , and n is 0.
111. A method according to Claim 106 wherein R is <IMG>,
R1 is -i-C4H9, R2 is -i-C4H9, and n is 0.
112. A method according to Claim 106 wherein R is <IMG>,
R1 and R2 together are <IMG> and n is 0.
113. A method according to Claim 106 wherein R is <IMG>,
R1 is -C2H5, R2 is <IMG> , and n is 0.
114. A method according to Claim 106 wherein R is <IMG>,
R1 is -n-C3H7, R2 is <IMG> , and n is 0.
115. A method according to Claim 106 wherein R is <IMG>,
R1 is -i-C3H7, R2 is <IMG> , and n is 0.
116. A method according to Claim 106 wherein R is <IMG>,
R1 is -C2H5, R2 is -n-C4H9, and n is 0.
42

117. A method according to Claim 106 wherein R is <IMG>,
R1 is -CH2CH=CH2, R2 is <IMG> , and n is 0.
118. A method according to Claim 106 wherein R is <IMG>,
R1 is -s-C4H9, R2 is <IMG> , and n is 0.
119. A method according to Claim 106 wherein R is <IMG>,
R1 is <IMG> , and R2 is <IMG> , and n is 0.
120. A method according to Claim 106 wherein R is <IMG>,
R1 is -C2H5, R2 is -CH2CH=CH2, and n is 0.
121. A method according to Claim 106 wherein R is <IMG>,
R1 is -C2H5, R2 is <IMG> , and n is 0.
122. A method according to Claim 106 wherein R is <IMG>,
R1 is -C2H5, R2 is <IMG>, and n is 0.
123 A method according to Claim 106 wherein R is <IMG>,
R1 is -C2H5, R2 is <IMG>, and n is 0.
124. A method according to Claim 106 wherein R is <IMG>,
R1 is -n-C3H7, R2 is i-C3H7, and n is 0.
125. A method according to Claim 106 wherein R is <IMG>,
R1 is -s-C4H9, R2 is -s-C4H9, and n is 0.
126. A method according to Claim 106 wherein R is <IMG>,
R1 and R2 together are <IMG> and n is 0.
43

127. A method according to Claim 106 wherein R is <IMG>,
R1 is -i-C4H9, R2 is -s-C4H9, and n is 0.
128. A method according to Claim106 wherein R is <IMG>,
R1 is <IMG>, R2 is <IMG>, and n is 0.
129. A method according to Claim 106 wherein R is <IMG>,
R1 and R2 together are and n is 0.
<IMG>
130. A method according to Claim 106 wherein R is <IMG>,
R1 is -n-C3H7, R2 is -n-C3H7, and n is 1.
131. A method according to Claim 106 wherein R is <IMG>,
R1 is -C2H5, R2 is CH2CH=CH2, and n is 1.
132. A method according to Claim 106 wherein R is <IMG>,
R1 is -C2H5, R2 is -n-C4H9, and n is 1.
133. A method according to Claim 106 wherein R is <IMG>,
R1 is -C2H5, R2 is -s-C4H9, and n is 1.
134. A method according to Claim 106 wherein R is <IMG>,
R1 is -C2H5, R2 is <IMG>, and n is 1.
135. A method according to Claim 106 wherein R is <IMG>,
R1 is -C2H5, R2 is <IMG>, and n is 1.
44

136. A method according to Claim 106 wherein R is <IMG>,
R1 is -C2H5, R2 is <IMG>, and n is 1.
137. A method according to Claim 106 wherein R is <IMG>,
R1 is -C2H5, R2 is <IMG>, and n is 1.
138. A method according to Claim 106 wherein R is <IMG>,
R1 is -n-C3H7, R2 is -i-C3H7, and n is 1.
139. A method according to Claim 106 wherein R is <IMG>,
R1 is -n-C3H7, R2 is <IMG>, and n is 1.
140. A method according to Claim 106 wherein R is <IMG>,
R1 is -i-C3H7, R2 is <IMG>, and n is 1.
141. A method according to Claim 106 wherein R is <IMG>,
R1 is CH2CH=CH2, R2 is <IMG>, and n is 1.
142. A method according to Claim 106 wherein R is <IMG>,
R1 is n-C4H9, R2 is <IMG>, and n is 1.
143. A method according to Claim 106 wherein R is <IMG>,
R1 is i-C4H9, R2 is i-C4H9, and n is 1.
144. A method according to Claim 106 wherein R is <IMG>,
R1 is s-C4H9, R2 is s-C4H9, and n is 1.
145. A method according to Claim 106 wherein R is <IMG>,
R1 is s-C4H9, R2 is <IMG>, and n is 1.

146. A method according to Claim 106 wherein R is <IMG>,
R1 is <IMG>, R2 is <IMG>, and n is 1.
147. A method according to Claim 106 wherein R is <IMG>,
R1 and R2 together are <IMG> and n is 1.
148. A method according to Claim 106 wherein R is <IMG>,
R1 and R2 together are <IMG> and n is 1.
149. A method according to Claim 106 wherein R is <IMG>,
R1 is -i-C4H9, R2 is -s-C4H9, and n is 1.
150. A method according to Claim 106 wherein R is <IMG>,
R1 is <IMG>, R2 is <IMG>, and n is 1.
151. A method according to Claim 106 wherein R is <IMG>,
R1 and R2 together are <IMG> and n is 1.
152. A method according to Claim 106 wherein R is <IMG>,
R1 is -C2H5, R2 is -n-C4H9, and n is 0.
153. A method according to Claim 106 wherein R is <IMG>,
R1 is -C2H5, R2 is -s-C4H9, and n is 0.
46

154. A method according to Claim 106 wherein R is <IMG>,
R1 is -C2H5, R2 is <IMG>, and n is 0.
155. A method according to Claim 106 wherein R is <IMG>,
R1 is -n-C3H7, R2 is -n-C3H7, and n is 0.
156. A method according to Claim 106 wherein R is <IMG>,
R1 is -n-C4H9, R2 is <IMG>, and n is 0.
157. A method according to Claim 106 wherein R is <IMG>,
R1 is -i-C4H9, R2 is -i-C4H9, and n is 0.
158. A method according to Claim 106 wherein R is <IMG>,
R1 is -s-C4H9, R2 is -s-C4H9, and n is 0.
159. A method according to Claim 106 wherein R is <IMG>,
R1 is -i-C4H9, R2 is -s-C4H9, and n is 0.
160. A method according to Claim 106 wherein R is <IMG>,
R1 and R2 together are <IMG> and n is 0.
161. A method according to Claim 106 wherein R is <IMG>,
R1 is <IMG>, R2 is <IMG>, and n is 0.
162. A method according to Claim 106 wherein R is <IMG>,
R1 and R2 together are <IMG> and n is 0.
47

163. A method according to Claim 106 wherein R is <IMG>,
R1 and R2 together are <IMG> , and n is 1.
164. A method according to Claim 106 wherein R is <IMG>,
R1 and R2 together are <IMG> and n is 1.
165. A method according to Claim 106 wherein R is <IMG>
R1 is <IMG> , R2 is <IMG> , and n is 1.
166. A method according to Claim 106 wherein R is <IMG>,
R1 is -C2H5, R2 is n-C4H9, and n is 0.
167. A method according to Claim 106 wherein R is <IMG>,
R1 is -C2H5, R2 is -s-C4H9.
168. A method according to Claim 106 wherein R is <IMG>,
R1 is -C2H5, R2 is <IMG>, and n is 0.
169. A method according to Claim 106 wherein R is <IMG>,
R1 is -n-C3H7, R2 is -n-C3H7, and n is 0.
170. A method according to Claim 106 wherein R is <IMG>,
R1 is -C4H9, R2 is -i-C4H9, and n is 0.
171. A method according to Claim 106 wherein R is <IMG>,
R1 is <IMG>, R2 is <IMG>, and n is 0.
48

172. A method according to Claim 106 wherein R is <IMG>,
R1 is -i-C4H9, R2 is -s-C4H9, and n is 0.
173. A method according to Claim 106 wherein R is <IMG>,
R1 is -s-C4H9, R2 is -s-C4H9, and n is 0.
174. A method according to Claim 106 wherein R is <IMG>,
R1 and R2 together are <IMG> and n is 0.
175. A method according to Claim 106 wherein R is <IMG>,
R1 and R2 together are <IMG> and n is 0.
176. A method according to Claim 106 wherein R is <IMG>,
R1 is -n-C4H9, R2 is -n-C4H9, and n is 0.
177. A method according to Claim 106 wherein R is <IMG>,
R1 and R2 together are <IMG> and n is 0.
178. A method according to Claim 106 wherein R is
<IMG> , R1 is C2H5, R2 is n-C4H9, and n is 0.
49

179. A method according to Claim 106 wherein R is
<IMG> , R1 is C2H5, R2 is i-C4H9, and n is 0.
180. A method according to Claim 106 wherein R is
<IMG> , R1 is C2H5, R2 is sec.-C4H9, and n is 0.
181. A method according to Claim 106 wherein R is
<IMG> , R1 is n-C3H7, R2 is n-C3H7, and n is 0.
182. A method according to Claim 106 wherein R is
<IMG>, R1 is n-C3H7, R2 is i-C3H7, and n is 0.
183. A method according to Claim 106 wherein R is
<IMG> , R1 is allyl, R2 is allyl, and n is 0.
184. A method according to Claim 106 wherein R is
<IMG> , R1 is i-C3H7, R2 is i-C4H9, and n is 0.

185. A method according to Claim 106 wherein R is
<IMG> , R1 is i-C4H9, R2 is i-C4H9, and n is 0.
186. A method according to Claim 106 wherein R is
<IMG> , R1 is sec.-C4H9, R2 is sec.-C4H9, and n is 0.
187. A method according to Claim 106 wherein R is
<IMG> , R1 is i-C4H9, R2 is sec.-C4H9, and n is 0.
188. A method according to Claim 106 wherein R is
<IMG> , R1 and R2 taken together are <IMG> , and n is 0.
189. A method according to Claim 106 wherein R is
<IMG> , R1 is C2H5, R2 is allyl, and n is 0.
190. A method according to Claim 106 wherein R is
<IMG> , R1 is C2H5, R2 is cyclohexyl, and n is 0.
51

191. A method according to Claim 106 wherein R is
<IMG> , R1 is n-C4H9, R2 is cyclopropylmethyl, and n is 0.
192. A method according to Claim 106 wherein R is
<IMG> , R1 and R2 taken together are <IMG> and n is 0.
193. A method according to Claim 106 wherein R is
<IMG> , R1 is cyclopropylmethyl, R2 is cyclopropylmethyl, and
n is 0.
194. A method according to Claim 106 wherein R is
<IMG> , R1 and R2 taken together are <IMG> , and n is 0.
195. A method according to Claim 106 wherein R is
<IMG> , R1 is C2H5, R2 is sec.-C4H9, and n is 1.
196. A method according to Claim 106 wherein R is
<IMG> , R1 is i-C4H9, R2 is sec.-C4H9, and n is 1.
52

197. A method according to Claim 106 wherein R is
<IMG> , R1 is C2H5, R2 is n-C4H9, and n is 1.
198. A method according to Claim 106 wherein R is
<IMG> , R1 is C2H5, R2 is i-C4H9, and n is 1.
199. A method according to Claim 106 wherein R is
<IMG> , R1 is C3H7, R2 is i-C3H7, and n is 1.
200. A method according to Claim 106 wherein R is
<IMG> , R1 is i-C3H7, R2 is i-C4H9, and n is 1.
201. A method according to Claim 106 wherein R is
<IMG> , R1 is sec.-C4H9, R2 is sec.-C4H9, and n is 1.
202. A method according to Claim 106 wherein R is
<IMG> , R1 is CH2CH=CH2, R2 is CH2CH=CH2, and n is 1.
53

203. A method according to Claim 106 wherein R is
<IMG> , R1 is n-C3H7, R2 is n-C3H7, and n is 1.
204. A method according to Claim 106 wherein R is
<IMG> , R1 is C2H5, R2 iS CH2CH=CH2, and n is 1,
205. A method according to Claim 106 wherein R is
<IMG> , R1 is C2H5, R2 is cyclohexyl, and n is 1.
206. A method according to Claim 106 wherein R is
<IMG> , R1 is C4H9, R2 is cyclopropylmethyl, and n is 1.
207. A method according to Claim 106 wherein R is
<IMG> , R1 and R2 taken together are <IMG> , and n is 1.
208. A method according to Claim 106 wherein R is
<IMG> , R1 is cyclopropylmethyl, R2 is cyclopropylmethyl, and
n is 1.
54

209. A method according to Claim 106 wherein R is
<IMG> , R1 is i-C4H9, R2 is i-C4H9, and n is 1.
210. A method according to Claim 106 wherein R is
<IMG> , R1 and R2 taken together are <IMG> , and n is 1.
211. A method according to Claim 106 wherein R is
<IMG> , R1 and R2 taken together are <IMG> , and
n is 1.

Description

Description of the Invention
This invention is directed to a novel class of thio-
carbamates, certain sulfoxide derivatives thereof and to the use
of said thiocarbamates and sulfoxides in controlling undesirable
vegetation. The compounds of the present invention are represented
by the following general structural formula:
(R) n p / Rl
R-CH2-S ~ -N \
R2 . ' ' .
wherein n is 0 or 1; R is selected from the group consisting of
tertiary butyi, cyclopropyl, cyclobutyl and cyclopentyl; and
Rl and R2 are individually selected from the group consisting
of alkyl, alkenyl, cyclopropylmethyl, cyclohexyl, phenyl and
benzyl or Rl and R2 together form an alkylene group or an
alkyl substituted alkylene group.
The term "alkyl" is meant to include straight and
branched chain alkyl groups having 1-6 carbon atoms. The term
"alkenyl" is meant to include straight and branched chain alkenyl
groups having 2-6 carbon atoms. The term "alkylene" is meant to
include alkylene groups containing 4-7 carbon atoms.
- The thiocarbamates, i.e. compounds of the above formula
wherein n equals 0, can be prepared by any of the known methods
of synthesis of thiocarbamates. Typical methods of preparing
thiocarbamates are disclosed in U.S. Patents No. 2,913,327,
2,983,747, 3,101,263, 3,133,947, 3,175,897 and 3,185,720. A
?articularly preferred method for preparing the thiocarbamates
is to react the appropriate chlorothioformate with the desired

amine. Appropriate starting materials for the preparation of the
individual thiocarbamates will be readily apparent to one skilled
in the art.
The sulfoxide derivatives of this invention, i.e. com-
pounds of the above formula wherein n = 1, can be prepared by
reacting an oxidizing agent such as peracetic acid or m-chloro-
peroxybenzoic acid with the thiocarbamate defined above. The
reaction is carried out in the presence of a solvent such as
chloroform, methylene chloride, benzene or toluene and at a
reduced temperature of from about -25C to about 65C. The
amount of oxidizing agent used must be at least 1 molar equivalent.
The carbamyl sulfoxides of this invention are excellent herbicides
and exhibit improved thermal stability
The following examples serve to illustrate the prepara-
tion of typcal thiocarbamate and sulfoxide compounds of this
invention and demonstrate their herbicidal activity.
EXAMPL~
This example illustrates the preparation of S-cyclo-
propylmethyl di-n-propyl thiocarbamate.
To a solution of 6.0 g (0.040 mole) of cyclopropylmethyl
chlorothioformate in 50 ml benzene is added 8.5 g (0.084 mole) of
di-n-propyl amine dissolved in 25 ml benzene while maintaining
the temperature below 30C. The reaction mixture was stirred
for 30 minutes, then washed with 50 ml 0.05 M hydrochloric

acid ~nd then twice with 50 ml pcrtions of water. The solution
wa8 then dried over anhydrous msgnesium sulfate, filteret and the
volatiles stripped off. A yield of 7.9 g (theory ~ 8.5 g) of
protuct having an N30 ~ 1.4S83 was obtained. The ~ructure of
the product was confirmed by NMR and IR.
EXAMPLE 2
This example illustrates the preparstion of S-cyclo- -
propylmethyl n-butyl cyclopropylmethyl thiocarbamate.
A solution of 3.44 g (0.021 mole) of n-butyl cyclopropyl-
methyl amine hydrochloride and 40.5 g (0.04 mole) of triethylamine
in 100 ml water is formed. Then, 3.0 g (0.020 mole) of cyclo-
propylmethyl chlorothioformate was added dropwise with stirring
~hile maintaining ~he temperature below 30C. Strring was
continued for 1 hour. The reaction mixture was then washed with
50 ml (0.05 mole) hydrochloric acid and twice with 50 ml portions
of water. The solution was dried over anhydrous magnesium sulfate,
filtered and the volatiles stripped off. A yield of 4.4 g (theory
4.8~ g) of product having ND30 : 1.4797 was obtained. Structure
of the product was conf~rmed by NMR and IR.
EXAMP~E 3
This example illustrates the preparation of S-cyclo-
propylmethyl n-butyl cyclopropylmethyl thiocarbamate sulfoxide.
A solution was formed by dissol~ing 4.3 g (0.0178 mole)
of S-cyclopropylmethyl n~bucyI cyclopropylmethyl thiocarbamate,
prepared as described in Example 2, in 75 ml methylene chloride

`L~7;~1
in a 250 ml three-necked flask equipped with a mechanical stir-
rer. The solution was cooled to 0C and 3,08 g (0,0178 mole) of
meta-chloroperoxybenzo~c acid was added in portions so as to
maintain the temperature between 0 snd 5C, The reaction m~xture
was allowed to warm to room temperature with stirring and stirring
was continued for about 90 minutes, After about 30 minutes
starch/potassium iodide test psper indicated complete disappear-
ance of peroxide from the reaction solution. The solution was
washed with ~0 ml of 5% potassium carbon~te and then twice with
50 ml portions of water, The solution was dried over anhydrous
mhgnesium sulfate, f~ltered and stripped of volatiles, A yield
of 4,5 g (theory - 4,6 g) of a product having N30 _ 1,4890 was
obtained, The structure of the product was confirmed by NMR and
IR.
EXAMPLE 4
This example illustrates the preparation of cyclobutyl-
methyl di-n-propyl thiocarbsmate,
In a 250 ml three-necked, round-bottom flssk equipped
with a mechanical stirrer and thermometer was placed a solution
of 1.6 g (0,04 mole) sodium hydroxide in 75 ml water and 4,05 g
(0,04 mole) di-n-propylamine, Rapid stirring was commenced and
6,57 g (0,04 mole) S-cyclobutylmethyl chlorothioformate was added
dropwise at a rate to maintain the temperature below 40C,
Following the addition the solution was stirred for one hour at
room temperature. The reaction mixture was separated into an
2S organic layer and a water layer and the water layer was washed ~-
with benzene. The resulting benzene layer was combined with the
--5--

organic layer ~nd washed with 50 ml lN hydrochloric ~c~t snd with
water snd the resul ing solution dried over anhytrous magnesium
sulfste. A yield of 8.6 g (theory ~ 9.17 g) of product having an
N30 1.4688 wss obtained Structure of the product W~8 confirmed
by NMR and IR.
EXAMPLE 5
This example illustrates the prep~ration of S-c~clo
butylmethyl di-n-propyl thioc~rbamate ~ulfoxide.
A solution was formed by dissolving 4.57 g (0.020 mole)
of S-cyclobutylmethyl di-n-propyl thiocarbamate, prepared as
described in Example 4, in 75 ml methylene chloride ~n a 250 ml
three-necked flask equipped with a mechanical stirrer. The
solution W8S cooled to 0C and 3.56 g (0.020 mole) of meta-chloro-
peroxybenzoic acid was added in portions so as to maintain the
temperature between 0 snd 5C. The reaction mixture was allowed
to wanm to room temperature with stirring ~nd stirring was
- continued for about 90 minutes. After about 30 minutes starch/
potassium iodide test psper indicated complete disappearance of
peroxide from the reaction solution. The solution was washed
with 70 ml of 5% potassium carbonate and then twice with 50 ml
portions of water. The solution was drie~ over anhydrous
magnesium sulfate, filtered, and stripped of volatiles. A yield
of 4.7 g (theory = 4.9 g) of product having ~ = 1.4793 was
obtained. The~tructure of the product was conf~rmed by NMR.
EXAMPLE 6
This example illustrates the preparation of S-cyclo-
pentylmethyl di-n-propyl thiocarbamate.
, .

f ~1
In a 250 ml three-necked round-bottom flask equipped
with a mecnanical st'rrer and thermometer were placed a solution
of 0.8 (0.02 mole) sodium hydroxide in 75 ml water and 2.02 g
(0.02 mole) di-n-propylamine. Rapid stirring was commenced and
3.58 g (0.02 mole) of S-cyclopentylmethyl chlorothioformate was
added dropwise at a rate to maintain the temperature below 40C.
Following the addition, the solution was stirred for one hour at
room temperature. The reaction mixture was separated into an
-organic layer and a water layer and the water layer washed with
benzene. The resulting benzene layer was combined with the
organic layer and washed with 50 ml LN hydrochloric acid and
with water and the resulting solution dired over anhydrous magnesium
sulfate. A yield of 4.6 g (theory = 4.87 g) of product having
N30 = 1.4719 was obtained. Structure of the produce was confirmed
by N~ and IR.
EXAMPLE 7
This example illustrates the preparation of S-neopentyl
butylethyl thiocarbamate.
In a 250 ml flask were placed a solution of 1.6 g
(0.04 mole) NaOH in 100 ml water and 4 0 g (0.04 mole) of butyl-
ethylamine. The mixture was stirred rapidly while 6.7 g (0.~4 mole)
of neopentylchlorothioformate was added dropwise, at a rate such
that the temperature was maint~ined at a maximum of 40C. After the
addition was complete, the mixture was stirred at room temperature
for 1 hour. The organic layer was separated, the aqueous layer
was washed with benzene and the combined organic phases were washed
with 50 ml of lN HCl, water, and dried over MgSO4. There was

obtained 7.2 g (78~/o g theoretical yield) of S-neopent~l butylethyl-
thioc~rbamate, N30 _ 1.4499.
EXA~fPLE 8
This example illustrates the preparation of S-neopentyl
hexahydro-lH-azepinecarbothioate sulfoxide.
In a 250 ml flask were placed 4.6 g (0.02 mole) S-
neopentyl hexahydro-lH-azepinecarbothioate and 75 ml methylene
chloride. The mixture was cooled to 5C with an ice/acetone bath,
and 3~5 g (0.02 mole) m-chloroperoxvbenzoic acid was added. The
reaction mixture was allowed to warm up to room temperature, then
further warmed to about 35-40C~ washed with 2 portions each of
50 ml of 5% aqueous potassiu.~ carbonate, followed by 2 portions
each of 50 ml water, dried over MgS04 and stripped of solvent.
There was obtained 4~3 g (86~/o of theoretical yield), of S-neopentyl
hexahydro-lH-azepinecarbothioate sulfoxide, N30 _ 1.4619.
Other compounds were prepared in an analagous manner
starting with the appropriate starting materials as outlined
above. The following Table I lists compounds representative of
those embodied by the present invention, including those whose
preparation is described above. Compound numbers have been
assigned ~o them and are used for identification throughout the
balance of this specification.

a~
TABLE I
()n 8~Rl
\R2
Com-
pound
No. R Rl ~ n
D- -C2H5 ~ C4H9
2 D- -C2H5 g C4H9
3 D- -n-C3H7 n C3H7 0
4 D- -n-C4Hg _n-C4H9
D- -n-C4Hg -CH2~
6 D- -i-C4H9 -i-C4H9
D- ~ CH2--CH2 i 2
CH2--CH2--CH2
8 D- -C2H5 -CH2~
g D- -n-C3H7 CH2<¦ 0
D~ C3H7
11 D -CH2CH-CH2 CH2<1
12 C~ -s-C4H9 2-'a
13 D~- -CH2~ -CH2~<1 o

7f~1
TAB~E I (con ' t)
Com-
potmd
No. R Rl --2
14 D- -C2H5 -CH2CH-CH2
D- C2H5 ~
16 D- -C2H5 ~
17 D- -C2H5 CH2~
18 ~ -n-C3H7 i-C3H7
19 D- -S-C4Hg ~ C4Hg . O
D- ~2H5 0
~H--CH2 2
CH3
21 ~ -i-C4Hg -s-C4H9
22 D- -CH2-<1 CH2-<1 . O
23 D- CH2--CH2--CH2
~ ~ CH2
CH2~U2'--CH2 ~,
24 D- -n-C3H7 -n-C3H7
C'~ -C2H5 -CH2CHSCH2
26 C>- -C2H5 -n-C4H9
27 D- -C2H5 -s-C4H9
-io-

l~'f ~
TABLE I (con't)
Com-
pound
No. R Rl ~2 n
- 28 ~- -C2H5 -CH2~
29 ~ -C2H5 _~ 1
~ -C2H5 ~
31 D- -C2H5 -CH2~3 1
32 D- -n-C3H7 -i-C3H7
33 D- -n-C3H7 CH2
34 D- -i-C3H7 -CH
D- ~H2CH8CH2 -CH2-~1
36 D; . n-C4Hg -CH2<¦ 1
37 D- i-C4Hg i-C4H9
38 ~ s-C4Hg ~-C4H9
D- 8-C4Hg -CH
D- -CH2<~ -CH~
41 D- F2H5
CH2
~H--CH2
CH3
42 D- CH2~H2 I H2
~CH2--CH2--C~2
-Ll-

TABLE I ~con't)
Co~-
pound
No. R ~1 R2
43 ~ -i-C4Hg -s-C4Hg
44 ~ -CH2 ~ -CH
~~ CH2----CH2
2--CH2--CH2
C2H5 -n-C4H9
47 ~ -C2H5 -s-C4Hg O
48 ~ C2H5. ~
49 ~ . -n-C3H7 -n-C3H7 O
O~ -n-C4Hg -CH2~
51 ~ -i-C4Hg -i-C4H9 ~:
52 -s-C4Hg -8-C4H9
5~ ~ -i~C4Hg -s-C4Hg
o ~CH2--CH2~CH2 ''
CH2--CH2--CH2
~ -CH2 ~ C~2 ~
56 ~
~CH2 --C~
~ CH2
CH CH2
C 3
-12-

7~
TABLE I (con't)
Com-
pound
No. R Rl --2
57 <~ / 2~H2~
C 2--CH2--C 2
58 0 ~CH2--CH2 IH2
~C~2--C~2~2
59 O- -CH2~ -CH2~
. 6 ' ,[~ -C2115 n C4~19 0
61 O~ S-C4H9
62 O- -C2~15 ~ O
63 O- -n-C3H -n C3H7
64 l~ -i-C4119 i-c4n9
~_ -CH2~ -CH2~<1 0
66 O- -~-C4H9
67 O~ -s-C4Hg -s-C4Hg O
68 O ~CH2~H2 1CH2
~CH2--CH2~H2
~,r ~~ 1 3.~

Table I (con't)
Com-
pound
No. R Rl R2 n
_
69 U f2H5 0
CH2~
~CH2
7H~12
CH3
U` -n-C4Hg -n-C4Hg O
71 0 / CH2---CH2--C ~ O
~ CH2
CH2--CH2~H2
~ ICH3 ~ .
72 CH3-C- C2H5n-C4Hg O
CH3
CH ' _ ~
73 CH3 ~ C2H5i C4H9
CH3
74 CH3-C- C2H5 sec.-C4H9 O
CH3
ICH3 .
C 3 IC 3 7 n-C3H7 O
C 3
ICH3
76 CH3-C- n C3H7 i-C3H7
CH3
B -14-
~ . " ~ .
. . . . . .

'7~1
TABLE I (con't)
Com-
pound
No. R Rl R2
ICH ~
77 CH3 IC allyl allyl 0
CH3
ICH3
78 CH3-C- i C3H7 i C4H9
CH3
CH3
79 CH3-C- i-C4Hg i-C4H9
CH3
~H3
CH3-C- sec.-C4Hg sec.-c4H9 0
CH3
F 3
81 CH3-F- i C4H9 sec.-C4Hg 0
CH3
ICH3 ~CH2-CH2-CH2
82 CH3-1C- \ ¦ 0
CH3 CH2-CH2-CH2
CH
83 CH3-C- C2H5 allyl
CH3
CH3
84 CH3-C- ' C2H5 cyclohexyl 0
CH3
FH3
CH3-C- n-C4Hg cyclopropyl- 0
H3
B.. ,.!~ -- 15

7~1
TABLE I (con't)
Com-
pound
No. R RlC H R2 n
l2 5
,CH3 CH2- CH
86 CH3-C- CH2 0
CH3 IH - C
CH3
CH
87 C 3 cyclopropyl- cyclopropyl- O
CH3 methyl . . methyl
ICH3 ~ CH2-CH? -C~
88 CH3-C- ~ CH2 0
CH3 CH2-CH2-CH2
~H3
89 CH3-C- C2H5 seC.-c4H9
CH3
CH3
CH3 C i C4H9 sec.-C4H9
CH3
CH3
91 CH3-C- C2H5 n-C4H9
CH3
ICH3
92 CH3-C- C2H5 i C4Hg
CH3
ÇH3
93 CH3-C- C3H7 i 3 7
CH3
94 CH3-C- i C3H7 i-C4H9
CH3
-16-
.B.~.
. " ~, .

r~ ~
a~
TABLE I (con~t)
Com-
pound
No. R Rl R2 n
CIH3
CH3-C~- sec.-C4Hg sec.-C4H9
CH3
~H3
96 CH3-CI- C ~ CH=CH2 CH2CH=CH2
CH3
CIH3
97 CH3-C- n~C3H7 n C3H7
CH3
CIH3
98 CH3-~- C2H5 CH2CH-CH2
CH3
CH3
99 CH3-C- C2H5 cyclohexyl
CH3
CIH3
100 CH3 C4Hg methyl
~C 2H5
~jCH3 / ~CH2 C ~
101 CH3-C- ~ ~ CH2
CH3 ICI~ C 2
CH3
iCH3
102 CH -IC- cyclopropyl- cyclopropyl-
3 CH3 methyl methyl
.~ -17-

7~
TABLE I (con ' t
Com-
R Rl 2
CH3
103 CH3-C- iC4H9 i-C4Hg
CH3
C! H3 /CH2-CH2-CH2
104 CH3-C-
~H3 CH2 CH2 CH2
Cl H3 ~CH2-CH2~
105 CH3-C- \ H2
CH3 CH2-CH2-CH2
-18-
~J ~" .

~ 7~1 .
Herbicidal Screenin~ Test
A~ previously mentioned, the novel thiocarbamates and
sulfoxides herein descr~bed are phytotoxic compounds which are
useful and valuable in controlling various plant species. Com-
pounds of this invention are tested as herbicides in the fol-
lowing manner.
Pre-emer~ence Her~icide Screenin~ Test
Using an analytical balance, 20 mg. of the compound to
be tested i8 weighed out on a piece of glassine weighing paper.
The paper and compound are placed in a 30 ml wide-mouth bottle
and 3 ml of acetone containing 1~ Tween 20~ (a polyoxyethylene
sorb~tan monolaurate) is added to d~ssolve the compound. If
the material is not soluble in acetone, another solvent such as
water, alcohol or dimethylformamide (DMF) is uæed instead. When
DMF is used, only 0.5 ml or less is used to dissolve the co~pound
snd then another solvent is used to make the volume up to 3 ml.
The 3 ml of solution is sprayed uniformly on the soil contained
in a small Styrofoam flat one day after planting weed seeds in
the flat of soil. A No. 152 DeVilbiss atomizer is used to apply
the spray using compresset air at a pre~sure of 5- lb/sq. in. The
rate of application is 8 lb/acre and the spray volume is 143
gal/acre. _
On the day preceding treatment, the Styrofoam flat,
which is 7 inches long, 5 inches wide and 2.75 inches deep, is
filled to a depth of 2 inches wlth loamy sand soil. Seeds of
seven different weed species are planted in individual rows
using one specles per row across the width of the flat. The
~ -L9-
.

seeds are covered with soil so that they are planted at a depth
of 0.5 inch. The seeds used are hairy crabgrass (Di~itaria
san~uinalis), yellow foxtail (Setaria ~lauca), redroot pigweed
~Amaranthus retroflexus), Indian mustard (Brassica ~uncea~,
S curly dock (Rumex crispus), watergrass (Echinochloa crus~alli),
and red oat (Avena _ativa). Ample seeds are planted to give
about 20 to 50 seedlings per row after emergence depending on
the size of the plants.
.
After treatment, the flats are placed in the greenhouse
at a temperature of 70 to 85F and watered by sprinkling. Two
weeks after treatment the degree of in~ury or control is deter-
mined by comparison with untreated check plants of the same age.
The in3ury rating from 0 to 1007o is recorded for each species
as percent control with ~/O representing no in~ury and 1007o
representing complete kill.
Post-emer~ence Herbicide Screenin~ Test
Seeds of six plant species, including hairy crabgrass,
watergrass, red oat, mustard, curly dock End Pinto beans
(Phaseolus vul~ar~s) are planted in the Styrofoam flats as des-
cribed above for pre-emergence screening. The flats are placed
in the greenhouse at 70 to 85F and watered daily with a sprinkler._
About 10 to 14 days after planting when the primary leaves of ~~
the bean plants are almost fully expanded and the first tri-
foliate leaves are just starting to fonm, the plants are sprayed.
The spray is prepared by weighing out 20 mg of the test compound,
dissolving it in 5 ml of acetone containing 1% Tween 20~ and then
adding 5 ml of water. The solution is sprayed on the foliage
-20-
... . .
': ' , . '

L~
using a No. 152 DeVilbiss atomizer at an air pressure of 5 lb/
8q . in. The spray concentration is 0.2 and the rate i8 8 lb/acre.
The spray volume is 476 gal/acre. In~ury ratings are recorded
14 days after treatment. The rating sys~em i8 the same as des-
ibed abovè in the pre-emergence test,
The results of these tests are shown in Table II.
TABLE II
Per cent contral at 8 lb/A . -
Compound Pre-Emer~ence ~ Post-Emergence
1 75 25
2 ~ 55 5
3 56 30
, . ....... . . . . . ..
4 - 54 ~ 43
6 55 25
- 7 59 52
8 87. 37
9 77 53
92 42
11 91 42
12 91 37
13 71 28
14 53 20
76 44
16 13 13
17 85 39
-Zl-

'7~1
TABLE II (con't)
Per cent control at 8 lb/A
Compound Pre-Emergence Post-Emergence
No.
18 S5 28
19 31 5
81 73
21 45 3
22 76 70
23 82 59
~4 ~8 63
- 25 67 ~5
26 94 77
27 92 58
28 88 66
29 85 86
6 8
31 38 31
32 92 74
33 97 87
34 91 79
.
79 78
36 96 79
99 83
38 68 60
39 97 81
63 48
41 99 84
42 89 67
. -22-
. . .

TABLE II (con1t)
Per cent control at 8 lb/A
Compound
_ N0. Pre-emer~ence Post-emer~ence
43 100 93
44 94 76
98 56
46 .. 40 42
47 44 72
48 . 51 46
49 52 34
51 31
5~ 51 35
52 26 3
53 49 5
54 24 46
55 69 50
56 81 58
57 . 68 81
58 17 73
59 76 66
52 47
61 51 27
62 17 35
63 30 41 ~
64 14 35
36 36
66 16 15
67 14 27
68 28 35

TABLE II (con't)
Per cent control at 8 lb/A
Compound
No. Pre-emer~ence Post-emer~ence
69 52 31
0 27
71 32 48
72 42 12
73 47 32
74 59 O
67 28
76 44 12
21 2
78 58 ^ O
79 42 3
~0 31 0
81 50 12
82 32 32
83 47 0
~4 33 43
28
86 55 28
87 82 45
88 65 55
89 91 83
gO 83 74
91 93 73
92 97 67
93 100 63
94 100 62
-

TABLE II (con't)
Per cent control at 8 lb/A
Compound
No. Pre-emergence Post-emer~ence
89 73
96 70 66
97 99 77
98 84 68
99 98 83
100 85 64
101 84 72
102 90 71
103 100 77
104 83 68
105 89 51
Average for seven plant species in the pre-emergence test and
for six plant species in the post-emergence test.
The herbicidal compounds of this invention are applied
to soil to control the growth of undesirable vegetation in th2
form of compositions or formulations containing the compound and
an inert carrier. Herbicidal formulations generally take the form
of dusts, wettable powders, granules, solutions, or emulsifiable
concentrates.
Dusts are free-flowing powder compositions containing
the herbicidal com?ound imprPgnated on a particulate carrier.
The ?articule size of the carrier is usually in the range of from
about 30 to 50 microns. Examples of suitable carriers are talc,
-25-
.

bentoinite, diatomaceous earth, and pyrophyllite. Anticaking
and antistatic agents can be added, if desired. The composition
generally contains up to 50% of active ingxedient.
Wettable powders are finely divided compositions com-
prising a particulate carrier impregnated with the herbicidal
compound and additionally contain one or more surface active
agent. The surface active agent promotes rapid dispersion of
the powder in aqueous medium to form stable, sprayable suspensions.
A wide variety of surface active agents can be used, for example,
long chain fatty alcohols and alkali metal salts of the sulfated
fatty alcohols; salts of sulfonic acid; esters of long chain
fatty acids; and polyhydric alcohols, in which the alcohol groups
are free, omega-substituted polyethylene glycols of relatively
long chain length. A list of surface active agents suitable for
use in agriculture formulations can be found in Pesticide
Formulations by Wade Van Valkenburg, Marcel Dekker, Inc., N.Y.
1973 at pages 79-84.
Granules comprise the herbicidal compound impregnated
on a particulate inert carrier having a particle size of about
1 to 2 millimeters in diameter. The granules can be made by
spraying a solution o the active ingredient in a volatile sol-
vent onto the granular carrier. Suitable carriers in preparation
of granules include clay, vermiculite, sawdust, granular carbon,
and the like.
The herbicidal compounds can also be applied to the
soil in the form of a solution in a suitable solvent. Solvents
frequently used in her~icidal formulations include kerosene,

fuel oil, xylene, petroleum fractions with boiling ranges above
xylene, and aromatic petroleum fractions rich in methylated
naphthalenes.
Emulsifiable concentrates consist of an oil solution of
the herbicide along with an emulsiying agent. Prior to use
the concentrate is diluted with water to form a suspended emulsion
of oil droplets. The emulsifiers used are usually a mixture of
anionic and nonionic surfactants. Other additives such as
spreading agents and stickers can be included in the emulsifiable
concentrate.
The compositions are applied to the soil to control
the growth of undesirable vegetation at a rate to provide 1-50
pounds per acre of active herbicidal ingredient. The amount of
actual ingredient used per acre will depend on overall cost and
desired result. It will be readily apparent to one skilled in
the art that compounds exhibiting lower herbicidal activity will
require a higher dosage rate for the same degree of control than
more active compounds.