HERBICIDES

HERBICIDE COMPOSITIONS

Abrégé anglais

IN THE UNITED STATES PATENT OFFICE
HERBICIDE COMPOSITIONS
Abstract of the Disclosure
Herbicidal active sulfoxide and sulfone
compounds are described herein. The compounds
have the following generic formula:
<IMG>
wherein n is 1 or 2; R is selected from the
group consisting of halophenyl, phenalkyl,
substituted phenalkyl, wherein said substituents
can be selected from halogen and haloalkyl; R1
and R2 can be the same or different and can be
selected from the group consisting of lower
alkyl, cycloalkyl, alkynyl and benzyl.

Revendications

The embodiments of the invention in which an exclusive
property or privilege is claimed are defined as follows:
1. A compound represented by the following generic
formula:
<IMG> .
wherein n is 1 or 2; R is selected from the group consisting of
halophenyl, phenalkyl, substituted phenalkyl, wherein said sub-
stituents can be selected from halogen, alkyl and haloalkyl; R1
and R2 can be the same or different and can be selected from the
group consisting of lower alkyl, cycloalkyl, alkenyl, alkynyl
and benzyl with the proviso that when R is benzyl R1 and R2
are not both-sec-C4H9.
2. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -C2H5, R2 is -C2H5 and n is 2.
3. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -C2H5, R2 is -C2H5 and n is 1.
4. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is n-C3H7, R2 is n-C3H7, and n is 1.
5. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -CH3, R2 is -CH(CH3)-C?CH and n is 1.

6. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -C2H5, R2 is i-C4H9 and n is 1.
7. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is n-C3H7, R2 is n-C3H7 and n is 1.
8. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is n-C3H7, R2 is n-C4H9 and n is 1.
9. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is n-C3H7, R2 is n-C3H7 and n is 1,
10. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is n-C3H7, R2 is n-C3H7 and n is 1.
11. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -C2H5, R2 is i-C4H9 and n is 2.
12. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is n-C3H7, R2 is <IMG> and n is 1.
21

13. The compound as set forth in Claim 1 wherein R is
<IMG> , R1 is -C2H5, R2 is -C2H5 and n is 1.
14. The compound as set forth in Claim 1 wherein R is
<IMG> , R1 is n-C3H7, R2 is n-C3H7 and n is 1.
15. The compound as set forth in Claim 1 wherein R is
<IMG> , R1 is n-C3H7, R2 is n-C3H7 and n is 1.
16. The compound as set forth in Claim 1 wherein R is
<IMG> , R1 is -C2H5, R2 is n-C4H9 and n is 1.
17. The compound as set forth in Claim 1 wherein R is
<IMG> , R1 is n-C3H7, R2 is n-C3H7 and n is 2.
18. The compound as set forth in Claim 1 wherein R is
<IMG> , R1 is n-C3H7, R2 is n-C3H7 and n is 2.
19. The compound as set forth in Claim 1 wherein R is
<IMG> , R1 is -C2H5, R2 is <IMG> and n is 1.
22

20. The compound as set forth in Claim 1 wherein R is
<IMG> , R1 is -C2H5, R2 iS -CH2CH=CH2 and n is 1.
21. The compound as set forth in Claim 1 wherein R is
<IMG> , R1 is n-C3H7, R2 is n-C3H7 and n is 2.
22. The compound as set forth in Claim 1 wherein R is
<IMG> , R1 is -C2H5, R2 is <IMG> and n is 1.
23. The compound as set forth in Claim 1 wherein R is
<IMG> , R1 is -C2H5, R2 is -C2H5 and n is 1.
24. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -n-C4H9, R2 is -n-C4H9 and n is 1.
25. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -n-C4H9, R2 is -i-C4H9 and n is 1.
26. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -n-C4H9, R2 is -sec-C4H9 and n is 1.
27. The compound as set forth in Claim 1 therein R is
<IMG>, R1 is -i-C4H9, R2 is -sec-C4H9 and n is 1.
28. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -C2H5, R2 is -n-C4H9 and n is 2.
29. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -C2H5, R2 is -sec-C4H9 and n is 2.
23

30. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -n-C4H9, R2 is -n-C4H9 and n is 2.
31. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -n-C4H9, R2 is -i-C4H9 and n is 2.
32. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -n-C4H9, R2 is -sec-C4H9 and n is 2.
33. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -i-C4H9, R2 is -i-C4H9 and n is 2.
34. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -i-C4H9, R2 is -sec-C4H9 and n is 2.
35. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -C2H5, R2 is -n-C4H9 and n is 1.
36. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -C2H5, R2 is -sec-C4H9 and n is 1.
37. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -C2H5, R2 is -t-C4H9 and n is 1.
38. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -n-C3H7, R2 is -i-C4H9 and n is 1.
39. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -n-C3H7, R2 is -sec-C4H9 and n is 1.
24

40. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -i-C3H7, R2 is -n-C4H9 and n is 1.
41. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -i-C3H7, R2 is -i-C4H9 and n is 1.
42. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -C2H5, R2 is -n-C4H9 and n is 1.
43. The compound as set forth in Claim 1 wherein R is
<IMG>,R1 is -n-C2H5, R2 is -i-C4H9 and n is 1.
44. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -n-C4H9, R2 is -n-C4H9 and n is 1.
45. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -C2H5, R2 is <IMG>, and n is 1.
46. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -C2H5, R2 is -i-C4H9 and n is 1.
47. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -n-C4H9, R2 is -n-C4H9 and n is 1.
48. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -C2H5, R2 is -n-C4H9 and n is 1.

49. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -C2H5, R2 is -n-C4H9 and n is 1.
50. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -C2H5, R2 is -i-C4H9 and n is 1.
51. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -n-C3H7, R2 is -n-C3H7 and n is 1.
52. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -n-C4H9, R2 is -n-C4H9 and n is 1.
53. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is C2H5, R2 is <IMG> and n is 1.
54. The compound as set forth is Claim 1 wherein R is
<IMG>, R1 is i-C3H7, R2 is -n-C4H9 and n is 2.
55. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -i-C3H7, R2 is -i-C3H7 and n is 2.
56. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -CH3, R2 is -CH3 and n is 1.
57. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -C2H5, R2 is -n-C5H11 and n is 1.
58. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -C2H5, R2 is -sec-C5H11 and n is 1.
26

59. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -C2H5, R2 is <IMG> and n is 1.
60. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -n-C3H7, R2 is -n-C3H7 and n is 1.
61. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -C2H5, R2 is -n-C4H9 and n is 1.
62. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -C2H5, R2 is -sec-C4H9 and n is 1.
63. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -CH3, R2 is -sec-C4H9 and n is 1.
64. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 CH3, R2 is -sec-C5H11 and n is 1.
65. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -CH3, R2 is -CH(CH3)-CH(CH3)2 and n is 1.
66. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is C2H5, R2 is -i-C3H7 and n is 1.
67. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is C2H5, R2 is -CH2-CH=CH2 and n is 1.
27

68. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -C2H5, R2 is -CH(CH3)-CH(CH3)2 and n is 1.
69. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -i-C3H7, R2 is -1-C3H7 and n is 1.
70. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -i-C3H7, R2 is -n-C5H11 and n is 1.
71. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -i-C3H7, R2 is -sec-C5H11 and n is 1.
72. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -i-C4H9, R2 is -i-C4H9 and n is 1.
73. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -C2H5, R2 is -CH2-CH=CH2 and n is 1.
74. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -C2H5, R2 is -i-C4H9 and n is 1.
75. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -i-C4H9, R2 is -i-C4H9 and n is 1.
28

76. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -CH3, R2 is -i-C3H7 and n is 1.
77. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -CH3, R2 is -n-C6H13 and n is 1.
78. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -C2H5, R2 is -n-C3H7 and n is 1.
79. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -C2H5, R2 is -n-C6H13 and n is 1.
80. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -n-C3H7, R2 is -n-C5H11 and n is 1.
81. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -n-C3H7, R2 is -sec-C5H11 and n is 1.
82. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -n-C3H7, R2 is -CH(CH3)-CH(CH3)2 and n is 1.
83. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -CH3, R2 is <IMG> and n is 1.
84. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -n-C3H7, R2 is -i-C3H7, and n is 1.
29

85. The compound as set forth in Claim 1 wherein R is
<IMG> , R1 is -CH3, R2 is <IMG> and n is 1.
86. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -C2H5, R2 is <IMG> and n is 1.
87. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -C2H5, R2 is <IMG> and n is 1.
88. The compound as set forth in Claim 1 wherein R is
<IMG>, R1 is -n-C3H7, R2 is <IMG> and n is 1.
89. The compound as set forth in Claim 1 wherein R is
<IMG> , R1 is -C2H5, R2 is <IMG> and n is 1.
90. The method of controlling undesirable vegetation
comprising applying to the locus where control is desired an
herbicidally effective amount of a compound represented by the
following generic formula:
<IMG>
wherein n is 1 or 2; R is selected from the group consisting of
halophenyl, phenalkyl, substituted phenalkyl, wherein said sub-
stituents can be selected from halogen, alkyl and haloalkyl; R1
and R2 can be the same or different and can be selected from the
group consisting of lower alkyl, cycloalkyl, alkenyl, alkynyl
and benzyl with the proviso that when R is benzyl R1 and R2 are
not both sec C4-C9.
91. The method as set forth in Claim 90 wherein R is
<IMG>, R1 is -C2H5, R2 is -C2H5 and n is 2.

92. The method as set forth in Claim 90 wherein R is
<IMG>, R1 is -C2H5, R2 is -C2H5 and n is 1.
93. The method as set forth in Claim 90 wherein R is
<IMG>, R1 is n-C3H7, R2 is n-C3H7, and n is 1.
94. The method as set forth in Claim 90 wherein R is
<IMG>, R1 is -CH3, R2 is -CH(CH3)-C?CH and n is 1.
95. The method as set forth in Claim 90 wherein R is
<IMG>, R1 is -C2H5, R2 is i-C4H9 and n is 1.
96. The method as set forth in Claim 90 wherein R is
<IMG> , Rl is n-C3H7, R2 is n-C3H7 and n is 1.
97. The method as set forth in Claim 90 wherein R is
<IMG>, R1 is n-C3H7, R2 is n-C4H9 and n is 1.
98. The method as set forth in Claim 90 wherein R is
<IMG>,R1 is n-C3H7, R2 is n-C3H7 and n is 1.
99. The method as set forth in Claim 90 wherein R is
<IMG>, R1 is n-C3H7, R2 is n-C3H7 and n is 1.
100. The method as set forth in Claim 90 wherein R is
<IMG>, R1 is -C2H5, R2 is i-C4H9 and n is 2.
101. The method as set forth in Claim 90 wherein R is
<IMG>, R1 is n-C3H7, R2 is<IMG> and n is 1.
31

102. The method as set forth in Claim 90 wherein R is
<IMG>, R1 is -C2H5, R2 is -C2H5 and n is 1.
103. The method as set forth in Claim 90 wherein R is
<IMG>, R1 is n-C3H7, R2 is n-C3H7 and n is 1.
104. The method as set forth in Claim 90 wherein R is
<IMG>, R1 is n-C3H7, R2 is n-C3H7 and n is 1.
105. The method as set forth in Claim 90 wherein R is
<IMG>, R1 is -C2H5, R2 is n-C4H9 and n is 1.
106. The method as set forth in Claim 90 wherein R is
<IMG>, R1 is n-C3H7, R2 is n-C3H7 and n is 2.
107. The method as set forth in Claim 90 wherein R is
<IMG>, R1 is n-C3H7, R2 is n-C3H7 and n is 2.
108. The method as set forth in Claim 90 wherein R is
<IMG>,R1 is -C2H5, R2 is <IMG> and n is 1.
109. The method as set forth in Claim 90 wherein R is
<IMG>, R1 is -C2H5, R2 is -CH2CH=CH2 and n is 1.
110. The method as set forth in Claim 90 wherein R is
<IMG>, R1 is n-C3H7, R2 is n-C3H7 and n is 2.
32

111. The method as set forth in Claim 90 wherein R is
<IMG> , R1 is -C2H5, R2 is <IMG> and n is 1.
112. The method as set forth in Claim 90 wherein R is
<IMG> , R1 is -C2H5, R2 is -C2H5 and n is 1.
113. The method as set forth in Claim 90 wherein R is
<IMG> , R1 is -n-C4H9, R2 is -n-C4H9 and n is 1.
114. The method as set forth in Claim 90 wherein R is
<IMG> , R1 is -n-C4H9, R2 is -i-C4H9 and n is 1.
115. The method as set forth in Claim 90 wherein R is
<IMG> , R1 is -n-C4H9, R2 is -sec-C4H9 and n is 1.
116. The method as set forth in Claim 90 wherein R is
<IMG> , R1 is -i-C4H9, R2 is -sec-C4H9 and n is 1.
117. The method as set forth in Claim 90 wherein R is
<IMG> , R1 is -C2H5, R2 is -n-C4H9 and n is 2,
118. The method as set forth in Claim 90 wherein R is
<IMG> , R1 is -C2H5, R2 is -sec-C4H9 and n is 2.
119. The method as set forth in Claim 90 wherein R is
<IMG> ' R1 is -n-C4H9, R2 is -n-C4H9 and n is 2.
120. The method as set forth in Claim 90 wherein R is
<IMG> , R1 is -n-C4H9, R2 is -i-C4H9 and n is 2.
33

121. The method as set forth in Claim 90 wherein R is
<IMG> , Rl is -n-C4H9, R2 is -sec-C4H9 and D is 2.
122. The method as set forth in Claim 90wherein R is
<IMG> , Rl is -i-C4H9, R2 is -i-C4H9 and n is 2.
123- The method as set forth in Claim 90wherein R is
<IMG> , Rl is -i-C4H9, R2 is -sec-C4H9 and n is 2,
124. The method as set forth in Claim 90wherein R i
<IMG> , Rl is -C2H5, R2 is -n-C4H9 and n is 1.
125- The method as set forth in Claim 90wherein R is
<IMG> , Rl is -C2H5, R2 is -sec-C4H9 and n is 1.
126 . The method as set forth in Claim 90wherein R is
<IMG> , Rl is -C2H5, R2 is -t-C4H9 and n is 1.
127. The method as set forth in Claim 90 wherein R is
<IMG> , Rl is -n-C3H7, R2 is -i-C4H9 and n is 1.
128- The method as set forth in Claim90 wherein R is
<IMG> , Rl is -n-C3H7, R2 is -sec-C4H9 and n is 1.
129. The method as set forth in Claim90 wherein R is
<IMG> , Rl is -i-C3H7, R2 is -n-C4H9 and n is 1.
130, The method as set forth in Claim90 wherein R is
<IMG> , Rl is -i-C3H7, R2 is i C4H9 and n is
34

131. The method as set forth in Claim 90 wherein R is
<IMG> , Rl is -C2H5, R2 is -n-C4H9 and n is 1.
132. The method as set forth in Claim 90wherein R is
<IMG> , Rl is -C2H5, R2 is -i-C4Hg and n is 1.
133. The method as set forth in Claim 90wherein R is
<IMG> , Rl is -n-C4H9, R2 is -n-C4H9 and n is 1.
134 The method as set forth in Claim90 wherein R is
<IMG> , Rl is -C2H5, R2 is <IMG> and n is 1.
135 . The method as set forth in Claim90 wherein R is
<IMG> , Rl is -C2H5, R2 is -i-C4H9 and n is 1.
136 , The method as set forth in Claim90 wherein R is
<IMG> , Rl is -n-C4H9, R2 is -n-C4H9 and n is 1.
137. The method as set forth in Claim 90wherein R is
<IMG> , R1 is -C2H5, R2 is <IMG> and n is 1.
138 . The method as set forth in Claim 90wherein R is
<IMG> , Rl is -C2H5, R2 is -n-C4H9 and n is 1.
139 . The method as set forth in Claim 9owherein R is
<IMG> , Rl is -C2H5, R2 is -i-C4H9 and n is 1.
140. The method as set forth in Claim90 wherein R is
<IMG> , R1 is -n-C3H7, R2 is -n-C3H7 and n is 1.

141. The method as set forth in Claim 90 wherein R is
<IMG> , R1 is -n-C4H9, R2 is -n-C4H9 and n is 1.
142. The method as set forth in Claim 90 wherein R is
<IMG> , R1 is -C2H5, R2 is <IMG> and n is 1.
143. The method as set forth in Claim 90 wherein R is
<IMG> , R1 is i-C3H7, R2 is -n-C4H9 and n is 2.
144. The method as set forth in Claim 90 wherein R is
<IMG> , R1 is -i-C3H7, R2 is -i-C3H7 and n is 2.
145 . The method as set forth in Claim 90 wherein R is
<IMG> , R1 is -CH3, R2 is -CH3 and n is 1.
146. The method as set forth in Claim 90 wherein R is
<IMG> , R1 is -C2H5, R2 is -n-C5H11 and n is 1.
147 . The method as set forth in Claim 90 wherein R is
<IMG> , R1 is C2H5, R2 is -sec-C5H11 and n is 1.
148 . The method as set forth in Claim 90 wherein R is
<IMG> , R1 is -C2H5, R2 is <IMG> and n is 1.
149. The method as set forth in Claim 90 wherein R is
<IMG> , R1 is -n-C3H7, R2 is -n-C3H7 and n is 1.
36

150. The method as set forth in Claim 90wherein R is
<IMG> , Rl is -C2H5, R2 is -n-C4H9 and n is 1.
151. The method as set forth in Claim90 wherein R is
, Rl is -C2H5, R2 is -sec-C4Hg and n is 1.
<IMG>
152. The method as set forth in Claim90 wherein R is
<IMG> , Rl is -CH3, R2 is -sec-C4Hg and n is 1.
153. The method as set forth in Claim 90wherein R is
<IMG> , Rl is -CH3, R2 is -sec-C5Hll and n is 1.
154. The method as set forth in Claim 90wherein R is
<IMG> , Rl is -CH3, R2 is -CH(cH3)-cH(cH3)2 and n is 1.
155. The method as set forth in Claim90 wherein R is
<IMG> , Rl is -C2H5, R2 is -i-C3H7 and n is 1.
156. The method as set forth in Claim 90wherein R is
<IMG> , Rl is -C2H5, R2 is -CH2-CH=CH2 and n is 1.
157. The method as set forth in Claim 90wherein R is
<IMG> , Rl is -C2H5, R2 is -CH(CH3)-CH(CH3)2 and n is 1.
37

158 . The method as set forth in Claim 90 wherein R is
<IMG> , R1 is -i-C3H7, R2 is -i-C3H7 and n is 1.
159 . The method as set forth in Claim 90 wherein R is
<IMG> , R1 is -i-C3H7, R2 is -n-C5H11 and n is 1.
160 . The method as set forth in Claim 90 wherein R is
<IMG> R1 is -i-C3H7, R2 is -sec-C5H11
161. The method as set forth in Claim 90 wherein R is
<IMG> , R1 is -i-C4H9, R2 is -i-C4H9 and n is 1.
162. The method as set forth in Claim 90 wherein R is
<IMG> , R1 is -C2H5, R2 is -CH2-CH=CH2 and n is 1.
163. The method as set forth in Claim 90 wherein R is
<IMG> , R1 is -C2H5, R2 is -i-C4H9 and n is 1.
164. The method as set forth in Claim 90 wherein R is
<IMG> , R1 is -i-C4H9, R2 is -i-C4H9 and n is 1.
38

165 . The method as set forth in claim 90 wherein R is
<IMG> , R1 is -CH3, R2 is -i-C3H7 and n is 1.
166. The method as set forth in Claim 90 wherein R is
<IMG> , R1 is -CH3, R2 is -n-C6H13 and n is 1.
167 . The method as set forth in Claim 90 wherein R is
<IMG> , R1 is -C2H5, R2 is -n-C3H7 and n is 1.
168. The method as set forth in Claim 90 wherein R is
<IMG> , R1 is -C2H5, R2 is -n-C6H13 and n is 1.
169. The method as set forth in Claim 90 wherein R is
<IMG> , R1 is -n-C3H7, R2 is -n-C5H11 and n is 1.
170 . The method as set forth in Claim 90 wherein R is
<IMG> R1 is -n-C3H7, R2 is -sec-C5H11 and n is 1.
171. The method as set forth in Claim 90 wherein R is
<IMG> , R1 is -n-C3H7, R2 is -CH(CH3)-CH(CH3)2 and n is 1.
172. The method as set forth in Claim 90 wherein R is
<IMG> , R1 is -CH3, R2 is <IMG> and n is 1.
173. The method as set forth in Claim 90 wherein R is
<IMG> , R1 is -n-C3H7, R2 is -i-C3H7, and n is 1.
39

174 . The method as set forth in Claim 90 wherein R is
<IMG> , R1 is -CH3, R2 is <IMG> and n is 1.
175 . The method as set forth in Claim 90 wherein R is
<IMG> , R1 is -C2H5, R2 is <IMG> and n is 1.
176 . The method as set forth in Claim 90 wherein R is
<IMG> , Rl is -C2H5, R2 is <IMG> , and n is 1.
177. The method as set forth in Claim 90 wherein R is
<IMG> , Rl is -n-C3H7, R2 is <IMG> and n is 1.
178. The method as set forth in Claim 90 wherein R is
<IMG> Rl is -C2H5 R2 is <IMG> and n is 1.
179 . A process for manufacturing a compound having the
formula:
<IMG>
wherein n is 1 or 2; R is selected from the group consisting of
halophenyl, phenalkyl, substituted phenalkyl wherein said substi-
tuents are selected from halogen, alkyl and haloalkyl; Rl and R2
can be the same or different and can be selected from lower alkyl,
cycloalkyl, alkenyl, alkynyl and benzyl, with the ,proviso that when R is benzyl
Rl and R2 are not both sec C4Hg, comprising the steps of:
a) reacting an oxidizing agent with a thiocarbamate;
said thiocarbamate having the formula:
<IMG>
wherein said R, Rl and R2 have been previously
defined; 40
F 40

b) said reaction being carried out at a temperature
of between -25°C. and 65°C.;
c) said oxidizing agent being present in an amount
of at least one molar equivalent.
180. The process of claim 179 wherein said oxidizing
agent is m-chloroperoxybenzoic acid.
181. Compounds of the class of carbamoyl sulphoxides
having the general formula:
<IMG>
wherein R is selected from:
- halophenyl; and
- benzyl which may be substituted in the phenyl
group with alkyl containing 1 to 4 carbon
atoms and halogen;
and wherein R1 and R2 can be the same or different and can
be selected from:
- alkyl containing 1 to 4 carbon atoms; and
- cycloalkyl containing 4 to 7 carbon atoms with the
proviso that when R is benzyl R1 and R2 are not
both sec C4H9.
182. A process for manufacturing a compound having
the general formula:
<IMG>
wherein R is selected from:
- halophenyl; and
- benzyl which may be substituted in the phenyl
group with alkyl containing 1 to 4 carbon
atoms and halogen;
41

and wherein R1 and R2 can be the same or different and
can be selected from:
- alkyl containing 1 to 4 carbon atoms; and
-cycloalkyl containing 4 to 7 carbon atoms with the proviso that
when R is benzyl R1 and R2 are not both sec C4H9, comprising the steps of:
(a) reacting an oxidizing agent selected from:
(i) peracetic acid; and
(ii) m-chloroperoxybenzoic acid with a
thiocarbamate, said thiocarbamate
having the general formula:
<IMG>
wherein R, R1 and R2 have been previously
defined;
(b) said reaction being carried out at a temperature
between -25°C and 50°C; and
(c) said oxidizing agent being present in an amount
of one molar equivalent.
183. A method of controlling undesirable vegetation compris-
ing applying to the locus where control is desired an
effective amount of a compound represented by the general
formula:
<IMG>
wherein R is selected from:
- halophenyl; and
42

- benzyl which may be substituted in the phenyl
group with alkyl containing 1 to 4 carbon
atoms and halogen;
and wherein R1 and R2 can be the same or different and can
be selected from:
- alkyl containing 1 to 4 carbon atoms; and
- cycloalkyl containing 4 to 7 carbon atoms with the
proviso that when R is benzyl R1 and R2 are both not sec-C4H9.
184. The method as set forth in claim 183 wherein R is
<IMG> , R1 is n-C3H7 and R2 is <IMG>.
185. The method as set forth in claim 183 wherein R is
<IMG> , R1 is n-C3H7 and R2 is n-C3H7.
186. The method as set forth in claim 183 wherein R is
<IMG> , R1 is i-C4H9 and R2 is i-C4H9.
187. The method as set forth in claim 183 wherein R is
<IMG> , R1 is i-C3H7 and R2 is i-C3H7.
43

Description

li5S135
Description of th~ Invention
This invention is directed to a novel group of compounds
which may be generally described as sulfoxide and sulfone deri-
vàtives of thiocarbamates which are highly active herbicides.
The compounds of the present invention are represented by the
generic formula: ~ / R
-R-S()n-C~N\
R2
wherein n can be 1 or 2; R can be selected from the group con-
sisting of halophenyl, phenalkyl, substituted phenalkyl, wherein
said substituents can be selected from halogen, alkyl and halo-
alkyl; Rl and P~2 can be the same or different and can be selected
from the group consisting of lower alkyl, cycLoallcyl, alkenyl,
alkynyl and benzyl.
The above-noted compounds can be prepared by reacting
an oxidizing agent such as peracetic acid cr m-chloroperoxy-
benzoic acid with a thiocarbamate compound corresponding to the
following formula: ~ ~ R
R-S-C-N \
R2
wherein R, Rl and R2 have been defined above. The reaction is
carried out in the presence of a ~olvent such as chloroform,
methylene chloride, benzene or toluene, and at a reduced tempera-
ture of from about -25C. to about 65C. The amount of oxidizing
agent used must be at least one molar equivalent to form the sul-
foxide derivative and at least two molar equivalents to form the
sulfone derivatives.
~2-
,.

1155135
The thiocarbamate compounds are known herbicides and
their method of synthesis is known; see U.S. Patents 2,913,327,
2,983,747, 3,133,947, 3,175,897 and 3,185,720-~for example.
However, the use of these thiocarbamates as reactive intermediates
to form other compounds that also have pesticidal activity is
unexpected.
In order to illustrate the merits of the present inven-
tion the following examples are provided:
xample 1
O O
Cl ~ CE2-1-C-N
A solution was formed containing 7.5 g. of m-chloro-
peroxybenzoic acid in 100 cc. of methylene chloride in a reactionvessel. The temperature of this solution was regulated to 30C.,
wherein 4.4 g. (0.017 mole) of S-4-chlorobenzyl diethylthiocar-
bamate was added over a period of one minute. At the end of the
addition, a rapid reflux began and the temperature rose to 41C.
The reaction was allowed to take place for about 40 minutes,
wherein the mixture was cooled and filtered and the cake was
washed with two portions of 25 cc. of methylene chloride. The
combined filtrate was washed with four portions of 50 cc. of 5%
sodium carbonte solution and two portions of 50 cc. of water,
then dried over magnesium sulfate and concentrated in a rotary
evaporator, first under a water pump vacuum and finally under
high vacuum to yield 4.4 g. of product, n30 _ 1.5425. ~fter
standing for a short period, the liquid crystallized to yield
a product of 4.4 g. having a m.p. of 64-72C.

~ 1~5S135
Example 2
O O
Cl ~ - CH2-S-C-~ 2 5
~ solution was formed containing 10.7 g. (0.0525 mole)
of m-chloroperoxybenzoic acid in 200 ec. of methylene chloride.
This solution was cooled to -16C., wherein 12.9 g. (0.05 mole)
of S-4-chlorobenzyl diethylthiocarbamate was added over a period
of four mintues. The reaction was allowed to take place for one
hour, wherein the temperature was allowed to go to -5C. The
temperature was held at 5C. for another 30 mintues, wherein the
temperature was allowed to reach 21.5C. The solution was ~hen
cooled in an ice bath, wherein the cold mixture was filtered and
the cake was washed with two portions of 25 cc. of methylene
chloride. The combined filtrate was washed with four portions of
100 cc. of 5% solution of sodium carbonate and two portions of
100 cc. of water, dried over magnesium sulfate and concentrated
in a rotary evaporator, first under water pump vacuum and finally
15 under high vacuum to yield 12.3 g. of product, n30 ~ 1.5678.
This product was further distilled to yield 10.6 g. of product,
n30 _ 1.5680.
~xample 3
O O
~ 2 - i-C H
In a 500 ml. 3-necked flask equipped with a thermometer,
mechanical stirrer, and addition device were placed 250 ml. of
20 methylene chloride and 12.6 g. ~0.05 mole) of S-benzyl ethyl-
isobutylthiocarbamate dissolved in 25 ml. of methylene chloride.
Stirring was begun and the temperature lowered to -30C. with dry
-- 4 --

1~55~3S
ice. Then, 8.7 g. (0.05 mole) of m-chloroperoxybenzoic acid was
rapad,ly added and the temperature held at -30C. for 15 minutes.
The temperature then was allowed to rise to 0C. over a 30-minute
period and then up to 4C. The cold mixture was filtered and the
filtrate washed with three 50 ml. portions of 5~ potassium carbo-
nate solution, two 50 ml. portions of water and then dried over
magnesium sulfate and stripped to obtain a colorless viscous
liquid product weighing 13.5 g., n30 _ 1.5403.
Example 4
O O
C-M ~ 2 5
~ 2 ¦l i-C4H9
A solution was formed containing 17.3 g. (0.10 mole) of
m-chloroperoxybenzoic acid in 300 ml. of methylene chloride.
This mixture was warmed to 30C. whereupon 12.6 g. (0.05 mole) of
S-benzyl ethylisobutylthiocarbamate in 25 ml. of methylene chloride
was added at a rate such that gentle reflux was maintained. Stir-
ring at reflux was carried out for thirty minutes and then the
solution waC cooled to 5C. in an ice bath. The solid was filtered
off and washed with cold methylene chlorlde. The combined por-
tions of filtrate were washed with three 50 ml. portions of 5%
potassium carbonate solution, two 50 ml. portions of water, dried
over magnesium sulfate, and then stripped to obtain 14.0 g. of
product, n30 - 1.5255~
Other compounds were prepared in an analogous manner
starting with the appropriate starting materials as outlined above.

" `` 1155135
The following is a table of compounds representative of those
embodied by the present invention. Compound numbers have been
assigned to them and are used for identification throughout the
balance of the specification.
TABT~E I
R-S(O)n-C-N
Compound
No. R -1 -2 n
-CH2 ~ Cl -C2H5 -C2H5
-CH2 ~ Cl C2~5 -C2H5
3 ~ Cl C3 7 3 7
4 -CEI2 ~ -CH3 -CH(CH3)-C-CH
5 -CH2 ~ -C2H5 i-C4H9
6 -CH2 ~ n C3H7 n-c3H7
-CH2 ~ 3 7 n-C4H9
-- 6 --

~5S~3S
TABLE I (Cont~ )
Compound
No. R Rl R2 n
C24~ C3H7 3 7
3 6~ C 3 7 3 7
-CH2~9 -C2H5 i C4EI9 2
11 -CH;~ C3 7
5F3
12 -CH2~ -(~2H5 -C2H5
.
/CF3
13 -CH2 ~ 3 7 3 7
14 -CH2~--Cl C3H7 n C3H7
-CH2 {~Cl -C2H5 n-C4H9
CF3
16 -CH2--~ 3 7 n~C3H7 2
~ i!

155~35
TABLE I (Con t . )
Compound
No. R R R n
n-C3H7 n C3H7 2
18 -CH2~3 -C2H5 -CH2~
19 -CH2~CH3 -C2H5 -CH2CH=CH2
-CH2~CH3 n-C3H7 n~C3H7 2
21 -CH2~ -C2H5 -CH
F3
22 -CH2~ -C2H5 -C2H5
23 -CH2~3 -n-C4Hg -n-C4Hg
24 -CH2~3 -n-C4Hg -i-C4H9
-CH2~3 -n-C4Hg -sec-C4H9
26 -CH2~3 -i-C4Hg ~sec-C4Hg
27 -CH2~ -C2H5 -n-C4H9 2
28 -CH2~ -C2H5 -sec-C4H9 2
29 -CH2~ ~ C4H9 -n-C~Hg 2

~55~35
TABLE I (Cont.
Compound
~. R ~ R2
-CH~ ~ -n-C4Hg -i-C4H9 2
31 -CH2 ~ -n-C4Hg -sec-C4H9 2
32 -CH2 ~ -i-C4Hg -i-C4H9 2
33 -CH2 ~ C4~9 -sec~C4H 2
.
34 -CH2 ~ -C2H5 -n-C4H9
-CH2 ~ -C2H5 -sec-C4H9
36 -CH2 ~ -C2H5 -t-C4H9
37 -CH2 ~ -n-C3H7 -i-C4H9
.
38 -CH2 ~ -n-C3H7 -sec-C4Hg
39 -CH2 ~ -i-C3~17 ~n-C~Hg
-CH2 ~ i-C3H7 i C4~9
41 -CH2 ~ F3 -C2H5 -n-C4H9
,CF
42 -CH2 ~ -C2H5 -i-C4H9
43 -CH2 ~ CF3 -n-C4Hg -n C4H9

1155~35
TABLE I (~
Compound
No. R Rl R2 n
44 -CH2~ -C2H5 ~
-CH2~Cl -C2H5 -i-C4Hg 1
46 -CH2~Cl -n-C4Hg -n-C4H9
47 -CH2~3Cl -C2H5 {~ 1
48 -CH2~3cH3 C2H5 -n-C4H9
49 -CH2 g3CH3 -C2H5 -i-C4Hg
-CH2~CH3 -n-C3H7 -n-C3H7
51 -CH2~CH3 -n-C4Hg -n-C4Hg
52 -CH2g3CEl3 C2H5
53 -CH2~ i-C3H7 n C4H9 2
54 -CH2~ C3H7 - i-C3H7 2
-CE~2~ -CH3 -CH3
56 -CH2~ -C2H5 -n-C5Hll 1
57 -CH2~ -C2H5 -sec-C5Hll 1
-10-

1~5513S
~ Cont.
Compou~d
No. R Rl -2
58 -CH2 ~ -C2H
~1 '
59 -CH2~ -n-c3~7 -n-c3H7
C~
C~
CH2 ~ -C2H5 n C4H9
61 CH2 ~ -C2H5 -sec-C4H9
62 -CH2 ~ -CH3 sec C H
63 -CH2 ~ -CH3 -sec-C5Hll 1
64 -CH2 ~ -CH3 -CH(CH3)-C~(c~3)2
-CH2 ~ -C2H5 -i-C3H7
66 -CH2 ~ -C2H5
67 -CH2 ~ -C2H5 -cH(cH3)-cH(cH3)2
68 -CH2 ~ -i-C3H7 -i-C3H7 .1
69 -CH2 ~ -i-C3H7 n C5Hll

115513~
TABL.E I (Cont . )
Compound
No, R Rl R2 n
CH2~3 i C3H7 -sec-C5H11 1
71 -CH2~3 -i-C4Hg -i-C4H9
72 -CH2~3 -sec-C4H9 -sec-C4H9
73 -CH2~ -c2l~5 -CH2-CH=CH2 L
74 -CH2~3 -C2H5 -i-C4H9
C
-CH2~ -i-C4Hg -i-C4H9
7 6 -CH2~ -C~3 - i-C3H7
77 -CH2~3 -CH3 -n-C6H13
78 -CH2~ -C2H5 -n-C3H7
79 -CH2~3 ''C2H5 -n-C6H13
-CH2~3 -n-C3H7 -n-C5H11 1
81 -CH2~3 -n-C3H7 -sec-C5H11 1
-12-

1155~3S
TABLE I (Cont.)
Compound
No. R R R2 n
--1 _
82 -CH2 ~ -n C3H7 -CH(CH3~-CH(CH3)2
83 -CEI2 ~ -CH3 -CH
84 -CH2 ~ -n-C3H7 -i-C3H7
-CEI2 ~ C1 -CE~3 -CH2- ~ 1
86 -CH2 ~ C1 -C2EI5 -CH2 ~
87 -CH2 ~ Cl -C2H5 -CH2- ~ 1
88 -CEI2 ~ Cl -n-C3~I7 -CH
89 -CH2 ~ -C2H5 -CH
Herbicidal Screening Tests
.
As previously mentioned, the novel compounds herein des-
cribed are phytotoxic compounds which are useful and valuable in
controlling various plants species. Compounds of this invention
are tested as herbicides in the following manner.
Pre-emergence Herbicide Screening Test
Using an analytical halance, 20 mg. of the compound to be
-13-

llS5~3S
tested is 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~ is added to dissolve
the compound. If the material is not soluble in acetone, another
solvent such as water, alcohol or dimethylformamide (DMF) is used
instead. When DMF is used, only 0.5 ml. or less is used to
dissolve the compound and then another solvent is used to make
the volume up to 3 ml. The 3 ml. of solution is sprayed uni-
formly on the soil contained in a small Styrofoam flat one day
after planting weed seeds in the flat of soil. A Mo. 152
DeVilbiss atomizer is used to apply the spray using compressed
air at a pressure 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 with loamy sand soil. Seeds of
seven different weed species are pla~ed in individual rows using
one species per row across the width of the flat. The seeds are
covered with soil so that they are planted at a depth of 0.5
inch. The seeds used are hairy crabgrass (Di~itarla ~ ),
yellow foxtail (Sertaria ~lauca), redroot pigweed (~maranthus
retroflexus), Indian mustard (~rassica juncea) and curly dock
(Rumex crispus). ~mple 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 injury or control is deter-
mined by comparison with untreated check plants of the same age.
The injury rating from 0 to 100% is recorded for each species as
percent control with 0% representing no injury and 100% represent-
ing complete kill.
!~ -14-

" 1~55~35
Post-emergence Herbicide Screening Test
Seeds of six plant species, including hairy crabgrass,
watergrass, red oat, mustard, curly dock and Pinto beans
(Phaseolus vulgaris) 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
trifoliate leaves are just starting to form, 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 using a No. 152 DeVilbiss atomizer at an air
pressure of 5 lb./sq. in. The spray concentration is 0.2 and
the rate is 8 lb./acre. The spray volume is 476 gal./acre.
Injury ratings are recorded 14 days after treatment.
The rating system is the same as described above for the pre-
emergence test. The injury symptoms are also the same as listed
above for the pre-emergence test, except that IG (inhibited ger-
mination) is not used since the seeds have alread~ germinatedbefore treatment in the post-emergence screening test.
The results of these tests are shown in Table II.
-15-
.,.

~L15513~
TABLE II
HERBICIDAL ACTIVITY - SCREENING RESULTS
Per Cent Control~' at 8 lb./A
Compound
No. Pre-emer~ence Post-emergence
1 10 45
2 89 ` 88
3 8 0
4 53 18
99.7 93
6 99.9 87
7 99 - 87
8 76 75
9 88 60
. 90 76
11 - 91 25
12 75 15
13 93 32
14 87 72
82 48
16 27 10
17 37 17
18 57 20
19 68 40
17 42
22 92 63
23 90 47
24 90 75
9~ 72
26 91 75
-16-

~L~55~35
TABLÆ II (Cont.~
.
Gompound
No Pre-emerg~ence Post-emer~ence
27 27 15
31 14 0
34 88 73
99 - 95
36 46 48
37 100 85
38 - g8 gl
39 ~4 87 .
96 74
41 78 43
42 90 50
43 37 37
44 87 62
gO 75
46 64 63
47 ~1 7~
48 90 77
49 96 79
51 80 70
52 92 76
53 0 ` 32
54 4g 57
69 73
56 86 53
57 87 78
-17-

~15S~35
TABI,E II (Cont~
~.
Per Cent Control'; at 8 lb. /A
- Compound
__ No. Pre emer~ence Post-emergence
58 89 63
S9 77 45
58 43
61 96 - 48
62 99 83
~3 99 81
6~ g9.9 93
99 - 9
66 95 62
67 100 ~0
68 100 8
69 93 77
100 82
71 100 82
72 100 88 `
73 73 80
74 91 85
~9.6 85
76 96 91
77 64 83
78 98 83
79 88 78
91 79
81 100 91
82 100 92
83 38 32
-18-
~.

llSS135
T~BLE II (Cont.~
Per Cent Control* at 8 lb./A
Compound
No. Pre-emer~ence Post-eme~
84 90 78
85 21 0
87 62 O
88 42 0
89 67 40 -
Per Cent Control at 20 lb./A
Compound
No. Pre-emer~ence Post-emer~ence
21 43
28 29 --
29 0 7
30 - O 8
32 21 --
33 0 8
86 27 --
* Average for seven plant species in the pre-e~er~ence test '`
and for six plant species in the post-emerg~nce test.
The compounds of the present invention can be used in
any convenient form. Thus, the compounds can be made into emul-
sifiable liquids, emulsifiable concentrates, liquid, wettable po~-
der, powders, granular or any other convenient fo~rm, and applied
to the soil to control the undesired vegetation.
The terms lower alkyl, alkenyl and alkynyl are meant t~
include those compounds having straight or branched chain coni-
gurations having from 1 to 6 carbon atoms, inclusive.
-19-