CN1289477C - N-substituted phenyl carbamate compound with sterilization activity and method for preparing the same - Google Patents

N-substituted phenyl carbamate compound with sterilization activity and method for preparing the same Download PDF

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CN1289477C
CN1289477C CN 03124795 CN03124795A CN1289477C CN 1289477 C CN1289477 C CN 1289477C CN 03124795 CN03124795 CN 03124795 CN 03124795 A CN03124795 A CN 03124795A CN 1289477 C CN1289477 C CN 1289477C
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Prior art keywords
oily
pyridyl
formula
compound
meo
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CN1523013A (en
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刘卫东
王晓光
张承来
毛春晖
柳爱平
盛书祥
黄路
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Hunan Research Institute of Chemical Industry
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Hunan Research Institute of Chemical Industry
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Abstract

The present invention discloses an N-replacement phenyl carbamate compound which has bactericidal activity and is shown in a general formula (I), and a preparation method of the compound. In the general formula (I), R1, R2 and R6 are alkyl; R4 and R5 are respectively hydrogen or the alkyl, alkoxy which is replaced arbitrarily, alkenyl which is replaced arbitrarily, alkynyl which is replaced arbitrarily, aryl which is replaced arbitrarily, and hetero aryl which is replaced arbitrarily; R3 is the aryl which is replaced arbitrarily, or the hetero aryl which is replaced arbitrarily; n is from 0 to 2.

Description

Has N-substituted-phenyl amino formate compounds of fungicidal activity and preparation method thereof
Technical field the present invention relates to have fungicidal activity N-substituted-phenyl amino formate compounds and preparation method thereof.
Background technology German patent DE 4423612 discloses N-substituted-phenyl amino formate compounds, and this compounds has the characteristic of mycocide, but compound that the present invention relates to and fungicidal activity thereof do not have bibliographical information.
Summary of the invention the purpose of this invention is to provide the compound shown in (I) and preparation method thereof that has general formula, and (I) is as follows for general formula:
In the general formula (I): R 1, R 2, R 6It is alkyl; R 4, R 5Be respectively the thiazolinyl of hydrogen or alkyl, the alkoxyl group that replaces arbitrarily, replacement arbitrarily, the alkynyl that replaces arbitrarily, the aryl that replaces arbitrarily, any heteroaryl that replaces; R 3It is aryl that replaces arbitrarily or the heteroaryl that replaces arbitrarily; N is 0～2.
Alkyl: have the straight or branched alkyl of 1～6 carbon atom, for example methyl, ethyl, propyl group, sec.-propyl and butyl.
Thiazolinyl: have the straight or branched of 2～6 carbon atoms and can on any position, have two keys.For example vinyl, allyl group.
Alkynyl: have the straight or branched of 2～6 carbon atoms and can on any position, have three key.For example ethynyl, propargyl.
Aryl: comprise phenyl and naphthyl.
Heteroaryl: contain five-ring, six-ring or the fused heterocycle of one or more methyls, oxygen, sulfur heteroatom, for example furans, pyridine, pyrimidine, pyridazine, triazine, pyrazine, cumarone, thiazole, benzothiazole or pyrazoles.
General formula (I) also comprises because the two keys of carbon-nitrogen connect the Z type of different substituting group formation and the miscellany of E type rotamerism and arbitrary proportion thereof.
Further specify general formula of the present invention (I) compound with the compound of listing in the table 1, but do not limit the present invention.
Table 1
Numbering R1 R2 n R 3 R 4 R 5 R 6 Rerum natura
1 CH 3 CH 3 0 C 6H 5 H H CH 3 Oily
2 CH 3 CH 3 0 2-Cl-C 6H 4 H H CH 3 Oily
3 CH 3 CH 3 0 3-Cl-C 6H 4 H H CH 3 Oily
4 CH 3 CH 3 0 4-Cl-C 6H 4 H H CH 3 Oily
5 CH 3 CH 3 0 2-F-C 6H 4 H H CH 3 Oily
6 CH 3 CH 3 0 3-F-C 6H 4 H H CH 3 Oily
7 CH 3 CH 3 0 4-F-C 6H 4 H H CH 3 Oily
8 CH 3 CH 3 0 2-Br-C 6H 4 H H CH 3 Oily
9 CH 3 CH 3 0 3-Br-C 6H 4 H H CH 3 Oily
10 CH 3 CH 3 0 4-Br-C 6H 4 H H CH 3 Oily
11 CH 3 CH 3 0 2-Me-C 6H 4 H H CH 3 Oily
12 CH 3 CH 3 0 3-Me-C 6H 4 H H CH 3 Oily
13 CH 3 CH 3 0 4-Me-C 6H 4 H H CH 3 Oily
14 CH 3 CH 3 0 2-CF 3-C 6H 4 H H CH 3 Oily
15 CH 3 CH 3 0 3-CF 3-C 6H 4 H H CH 3 Oily
16 CH 3 CH 3 0 4-CF 3-C 6H 4 H H CH 3 Oily
17 CH 3 CH 3 0 2-MeO-C 6H 4 H H CH 3 Oily
18 CH 3 CH 3 0 3-MeO-C 6H 4 H H CH 3 Oily
19 CH 3 CH 3 0 4-MeO-C 6H 4 H H CH 3 Oily
20 CH 3 CH 3 0 2-CF 3O-C 6H 4 H H CH 3 Oily
21 CH 3 CH 3 0 3-CF 3O-C 6H 4 H H CH 3 Oily
22 CH 3 CH 3 0 4-CF 3O-C 6H 4 H H CH 3 Oily
23 CH 3 CH 3 0 4-F 2CHO-C 6H 4 H H CH 3 Oily
24 CH 3 CH 3 0 The 2-pyridyl H H CH 3 Oily
25 CH 3 CH 3 0 The 3-pyridyl H H CH 3 Oily
26 CH 3 CH 3 0 The 4-pyridyl H H CH 3 Oily
27 CH 3 CH 3 0 The 3-Cl-2-pyridyl H H CH 3 Oily
28 CH 3 CH 3 0 The 4-Cl-2-pyridyl H H CH 3 Oily
29 CH 3 CH 3 0 The 4-Cl-3-pyridyl H H CH 3 Oily
30 CH 3 CH 3 0 The 5-Cl-3-pyridyl H H CH 3 Oily
31 CH 3 CH 3 0 The 3-Cl-4-pyridyl H H CH 3 Oily
32 CH 3 CH 3 0 The 1-naphthyl H H CH 3 Oily
33 CH 3 CH 3 0 The 3-thiazolyl H H CH 3 Oily
34 CH 3 CH 3 0 2，4-diCl-C 6H 3 H H CH 3 Oily
35 CH 3 CH 3 0 2，5-diCl-C 6H 3 H H CH 3 Oily
36 CH 3 CH 3 0 3，4-diCl-C 6H 3 H H CH 3 Oily
37 CH 3 CH 3 0 2-Cl-4-Me-C 6H 3 H H CH 3 Oily
38 CH 3 CH 3 0 3-Cl-4-Me-C 6H 3 H H CH 3 Oily
39 CH 3 CH 3 0 2-F-4-Me-C 6H 3 H H CH 3 Oily
40 CH 3 CH 3 0 3-F-4-Me-C 6H 3 H H CH 3 Oily
41 CH 3 CH 3 0 2，4-diMe-C 6H 3 H H CH 3 Oily
42 CH 3 CH 3 0 2，5-diMe-C 6H 3 H H CH 3 Oily
43 CH 3 CH 3 0 3，4-diMe-C 6H 3 H H CH 3 Oily
44 CH 3 CH 3 0 2，4di(MeO)-C 6H 3 H H CH 3 Oily
45 CH 3 CH 3 0 3，4di(MeO)-C 6H 3 H H CH 3 Oily
46 CH 3 CH 3 0 3，5di(MeO)-C 6H 3 H H CH 3 Oily
47 CH 3 CH 3 0 3，5di(CF 3)-C 6H 3 H H CH 3 Oily
48 CH 3 CH 3 0 2，5-diCl-4-F-C 6H 2 H H CH 3 Oily
49 CH 3 CH 3 0 2，4，5-tri Cl-C 6H 2 H H CH 3 Oily
50 CH 3 CH 3 0 2，4，6-tri Cl-C 6H 2 H H CH 3 Oily
51 CH 3 CH 3 0 2，4，5-tri CH 3-C 6H 2 H H CH 3 Oily
52 CH 3 CH 3 0 2，4，6-tri CH 3-C 6H 2 H H CH 3 Oily
53 C 2H 5 CH 3 0 C 6H 5 H H CH 3 Oily
54 C 2H 5 CH 3 0 2-Cl-C 6H 4 H H CH 3 Oily
55 C 2H 5 CH 3 0 3-Cl-C 6H 4 H H CH 3 Oily
56 C 2H 5 CH 3 0 4-Cl-C 6H 4 H H CH 3 Oily
57 C 2H 5 CH 3 0 2-F-C 6H 4 H H CH 3 Oily
58 C 2H 5 CH 3 0 3-F-C 6H 4 H H CH 3 Oily
59 C 2H 5 CH 3 0 4-F-C 6H 4 H H CH 3 Oily
60 C 2H 5 CH 3 0 2-Br-C 6H 4 H H CH 3 Oily
61 C 2H 5 CH 3 0 3-Br-C 6H 4 H H CH 3 Oily
62 C 2H 5 CH 3 0 4-Br-C 6H 4 H H CH 3 Oily
63 C 2H 5 CH 3 0 2-Me-C 6H 4 H H CH 3 Oily
64 C 2H 5 CH 3 0 3-Me-C 6H 4 H H CH 3 Oily
65 C 2H 5 CH 3 0 4-Me-C 6H 4 H H CH 3 Oily
66 C 2H 5 CH 3 0 2-CF 3-C 6H 4 H H CH 3 Oily
67 C 2H 5 CH 3 0 3-CF 3-C 6H 4 H H CH 3 Oily
68 C 2H 5 CH 3 0 4-CF 3-C 6H 4 H H CH 3 Oily
69 C 2H 5 CH 3 0 2-MeO-C 6H 4 H H CH 3 Oily
70 C 2H 5 CH 3 0 3-MeO-C 6H 4 H H CH 3 Oily
71 C 2H 5 CH 3 0 4-MeO-C 6H 4 H H CH 3 Oily
72 C 2H 5 CH 3 0 2-CF 3O-C 6H 4 H H CH 3 Oily
73 C 2H 5 CH 3 0 3-CF 3O-C 6H 4 H H CH 3 Oily
74 C 2H 5 CH 3 0 4-CF 3O-C 6H 4 H H CH 3 Oily
75 C 2H 5 CH 3 0 4-F 2CHO-C 6H 4 H H CH 3 Oily
76 C 2H 5 CH 3 0 The 2-pyridyl H H CH 3 Oily
77 C 2H 5 CH 3 0 The 3-pyridyl H H CH 3 Oily
78 C 2H 5 CH 3 0 The 4-pyridyl H H CH 3 Oily
79 C 2H 5 CH 3 0 The 3-Cl-2-pyridyl H H CH 3 Oily
80 C 2H 5 CH 3 0 The 4-Cl-2-pyridyl H H CH 3 Oily
81 C 2H 5 CH 3 0 The 4-Cl-3-pyridyl H H CH 3 Oily
82 C 2H 5 CH 3 0 The 5-Cl-3-pyridyl H H CH 3 Oily
83 C 2H 5 CH 3 0 The 3-Cl-4-pyridyl H H CH 3 Oily
84 C 2H 5 CH 3 0 The 1-naphthyl H H CH 3 Oily
85 C 2H 5 CH 3 0 2，4-diCl-C 6H 3 H H CH 3 Oily
86 C 2H 5 CH 3 0 2，5-diCl-C 6H 3 H H CH 3 Oily
87 C 2H 5 CH 3 0 3，4-diCl-C 6H 3 H H CH 3 Oily
88 C 2H 5 CH 3 0 2-Cl-4-Me-C 6H 3 H H CH 3 Oily
89 C 2H 5 CH 3 0 3-Cl-4-Me-C 6H 3 H H CH 3 Oily
90 C 2H 5 CH 3 0 2-F-4-Me-C 6H 3 H H CH 3 Oily
91 C 2H 5 CH 3 0 3-F-4-Me-C 6H 3 H H CH 3 Oily
92 C 2H 5 CH 3 0 2，4-diMe-C 6H 3 H H CH 3 Oily
93 C 2H 5 CH 3 0 2，5-diMe-C 6H 3 H H CH 3 Oily
94 C 2H 5 CH 3 0 3，4-diMe-C 6H 3 H H CH 3 Oily
95 C 2H 5 CH 3 0 2，4di(MeO)-C 6H 3 H H CH 3 Oily
96 C 2H 5 CH 3 0 3，4di(MeO)-C 6H 3 H H CH 3 Oily
97 C 2H 5 CH 3 0 3，5di(MeO)-C 6H 3 H H CH 3 Oily
98 C 2H 5 CH 3 0 3，5di(CF 3)-C 6H 3 H H CH 3 Oily
99 C 2H 5 CH 3 0 2，5-diCl-4-F-C 6H 2 H H CH 3 Oily
100 C 2H 5 CH 3 0 2，4，5-tri Cl-C 6H 2 H H CH 3 Oily
101 C 2H 5 CH 3 0 2，4，6-tri Cl-C 6H 2 H H CH 3 Oily
102 C 2H 5 CH 3 0 2，4，5-tri CH 3-C 6H 2 H H CH 3 Oily
103 C 2H 5 CH 3 0 2，4，6-tri CH 3-C 6H 2 H H CH 3 Oily
104 CH 3 C 2H 5 0 C 6H 5 H H CH 3 Oily
105 CH 3 C 2H 5 0 2-Cl-C 6H 4 H H CH 3 Oily
106 CH 3 C 2H 5 0 3-Cl-C 6H 4 H H CH 3 Oily
107 CH 3 C 2H 5 0 4-Cl-C 6H 4 H H CH 3 Oily
108 CH 3 C 2H 5 0 2-F-C 6H 4 H H CH 3 Oily
109 CH 3 C 2H 5 0 3-F-C 6H 4 H H CH 3 Oily
110 CH 3 C 2H 5 0 4-F-C 6H 4 H H CH 3 Oily
111 CH 3 C 2H 5 0 2-Br-C 6H 4 H H CH 3 Oily
112 CH 3 C 2H 5 0 3-Br-C 6H 4 H H CH 3 Oily
113 CH 3 C 2H 5 0 4-Br-C 6H 4 H H CH 3 Oily
114 CH 3 C 2H 5 0 2-Me-C 6H 4 H H CH 3 Oily
115 CH 3 C 2H 5 0 3-Me-C 6H 4 H H CH 3 Oily
116 CH 3 C 2H 5 0 4-Me-C 6H 4 H H CH 3 Oily
117 CH 3 C 2H 5 0 2-CF 3-C 6H 4 H H CH 3 Oily
118 CH 3 C 2H 5 0 3-CF 3-C 6H 4 H H CH 3 Oily
119 CH 3 C 2H 5 0 4-CF 3-C 6H 4 H H CH 3 Oily
120 CH 3 C 2H 5 0 2-MeO-C 6H 4 H H CH 3 Oily
121 CH 3 C 2H 5 0 3-MeO-C 6H 4 H H CH 3 Oily
122 CH 3 C 2H 5 0 4-MeO-C 6H 4 H H CH 3 Oily
123 CH 3 C 2H 5 0 2-CF 3O-C 6H 4 H H CH 3 Oily
124 CH 3 C 2H 5 0 3-CF 3O-C 6H 4 H H CH 3 Oily
125 CH 3 C 2H 5 0 4-CF 3O-C 6H 4 H H CH 3 Oily
126 CH 3 C 2H 5 0 4-F 2CHO-C 6H 4 H H CH 3 Oily
127 CH 3 C 2H 5 0 The 2-pyridyl H H CH 3 Oily
128 CH 3 C 2H 5 0 The 3-pyridyl H H CH 3 Oily
129 CH 3 C 2H 5 0 The 4-pyridyl H H CH 3 Oily
130 CH 3 C 2H 5 0 The 3-Cl-2-pyridyl H H CH 3 Oily
131 CH 3 C 2H 5 0 The 4-Cl-2-pyridyl H H CH 3 Oily
132 CH 3 C 2H 5 0 The 4-Cl-3-pyridyl H H CH 3 Oily
133 CH 3 C 2H 5 0 The 5-Cl-3-pyridyl H H CH 3 Oily
134 CH 3 C 2H 5 0 The 3-Cl-4-pyridyl H H CH 3 Oily
135 CH 3 C 2H 5 0 The 1-naphthyl H H CH 3 Oily
136 CH 3 C 2H 5 0 2，4-diCl-C 6H 3 H H CH 3 Oily
137 CH 3 C 2H 5 0 2，5-diCl-C 6H 3 H H CH 3 Oily
138 CH 3 C 2H 5 0 3，4-diCl-C 6H 3 H H CH 3 Oily
139 CH 3 C 2H 5 0 2-Cl-4-Me-C 6H 3 H H CH 3 Oily
140 CH 3 C 2H 5 0 3-Cl-4-Me-C 6H 3 H H CH 3 Oily
141 CH 3 C 2H 5 0 2-F-4-Me-C 6H 3 H H CH 3 Oily
142 CH 3 C 2H 5 0 3-F-4-Me-C 6H 3 H H CH 3 Oily
143 CH 3 C 2H 5 0 2，4-diMe-C 6H 3 H H CH 3 Oily
144 CH 3 C 2H 5 0 2，5-diMe-C 6H 3 H H CH 3 Oily
145 CH 3 C 2H 5 0 3，4-diMe-C 6H 3 H H CH 3 Oily
146 CH 3 C 2H 5 0 2，4di(MeO)-C 6H 3 H H CH 3 Oily
147 CH 3 C 2H 5 0 3，4di(MeO)-C 6H 3 H H CH 3 Oily
148 CH 3 C 2H 5 0 3，5di(MeO)-C 6H 3 H H CH 3 Oily
149 CH 3 C 2H 5 0 3，5di(CF 3)-C 6H 3 H H CH 3 Oily
150 CH 3 C 2H 5 0 2，5-diCl-4-F-C 6H 2 H H CH 3 Oily
151 CH 3 C 2H 5 0 2，4，5-tri Cl-C 6H 2 H H CH 3 Oily
152 CH 3 C 2H 5 0 2，4，6-tri Cl-C 6H 2 H H CH 3 Oily
153 CH 3 C 2H 5 0 2，4，5-tri CH 3-C 6H 2 H H CH 3 Oily
154 CH 3 C 2H 5 0 2，4，6-tri CH 3-C 6H 2 H H CH 3 Oily
155 C 2H 5 C 2H 5 0 C 6H 5 H H CH 3 Oily
156 C 2H 5 C 2H 5 0 2-Cl-C 6H 4 H H CH 3 Oily
157 C 2H 5 C 2H 5 0 3-Cl-C 6H 4 H H CH 3 Oily
158 C 2H 5 C 2H 5 0 4-Cl-C 6H 4 H H CH 3 Oily
159 C 2H 5 C 2H 5 0 2-F-C 6H 4 H H CH 3 Oily
160 C 2H 5 C 2H 5 0 3-F-C 6H 4 H H CH 3 Oily
161 C 2H 5 C 2H 5 0 4-F-C 6H 4 H H CH 3 Oily
162 C 2H 5 C 2H 5 0 2-Br-C 6H 4 H H CH 3 Oily
163 C 2H 5 C 2H 5 0 3-Br-C 6H 4 H H CH 3 Oily
164 C 2H 5 C 2H 5 0 4-Br-C 6H 4 H H CH 3 Oily
165 C 2H 5 C 2H 5 0 2-Me-C 6H 4 H H CH 3 Oily
166 C 2H 5 C 2H 5 0 3-Me-C 6H 4 H H CH 3 Oily
167 C 2H 5 C 2H 5 0 4-Me-C 6H 4 H H CH 3 Oily
168 C 2H 5 C 2H 5 0 2-CF 3-C 6H 4 H H CH 3 Oily
169 C 2H 5 C 2H 5 0 3-CF 3-C 6H 4 H H CH 3 Oily
170 C 2H 5 C 2H 5 0 4-CF 3-C 6H 4 H H CH 3 Oily
171 C 2H 5 C 2H 5 0 2-MeO-C 6H 4 H H CH 3 Oily
172 C 2H 5 C 2H 5 0 3-MeO-C 6H 4 H H CH 3 Oily
173 C 2H 5 C 2H 5 0 4-MeO-C 6H 4 H H CH 3 Oily
174 C 2H 5 C 2H 5 0 2-CF 3O-C 6H 4 H H CH 3 Oily
175 C 2H 5 C 2H 5 0 3-CF 3O-C 6H 4 H H CH 3 Oily
176 C 2H 5 C 2H 5 0 4-CF 3O-C 6H 4 H H CH 3 Oily
177 C 2H 5 C 2H 5 0 4-F 2CHO-C 6H 4 H H CH 3 Oily
178 C 2H 5 C 2H 5 0 The 2-pyridyl H H CH 3 Oily
179 C 2H 5 C 2H 5 0 The 3-pyridyl H H CH 3 Oily
180 C 2H 5 C 2H 5 0 The 4-pyridyl H H CH 3 Oily
181 C 2H 5 C 2H 5 0 The 3-Cl-2-pyridyl H H CH 3 Oily
182 C 2H 5 C 2H 5 0 The 4-Cl-2-pyridyl H H CH 3 Oily
183 C 2H 5 C 2H 5 0 The 4-Cl-3-pyridyl H H CH 3 Oily
184 C 2H 5 C 2H 5 0 The 5-Cl-3-pyridyl H H CH 3 Oily
165 C 2H 5 C 2H 5 0 The 3-Cl-4-pyridyl H H CH 3 Oily
186 C 2H 5 C 2H 5 0 The 1-naphthyl H H CH 3 Oily
187 C 2H 5 C 2H 5 0 2，4-diCl-C 6H 3 H H CH 3 Oily
188 C 2H 5 C 2H 5 0 2，5-diCl-C 6H 3 H H CH 3 Oily
189 C 2H 5 C 2H 5 0 3，4-diCl-C 6H 3 H H CH 3 Oily
190 C 2H 5 C 2H 5 0 2-Cl-4-Me-C 6H 3 H H CH 3 Oily
191 C 2H 5 C 2H 5 0 3-Cl-4-Me-C 6H 3 H H CH 3 Oily
192 C 2H 5 C 2H 5 0 2-F-4-Me-C 6H 3 H H CH 3 Oily
193 C 2H 5 C 2H 5 0 3-F-4-Me-C 6H 3 H H CH 3 Oily
194 C 2H 5 C 2H 5 0 2，4-diMe-C 6H 3 H H CH 3 Oily
195 C 2H 5 C 2H 5 0 2，5-diMe-C 6H 3 H H CH 3 Oily
196 C 2H 5 C 2H 5 0 3，4-diMe-C 6H 3 H H CH 3 Oily
197 C 2H 5 C 2H 5 0 2，4di(MeO)-C 6H 3 H H CH 3 Oily
198 C 2H 5 C 2H 5 0 3，4di(MeO)-C 6H 3 H H CH 3 Oily
199 C 2H 5 C 2H 5 0 3，5di(MeO)-C 6H 3 H H CH 3 Oily
200 C 2H 5 C 2H 5 0 3，5di(CF 3)-C 6H 3 H H CH 3 Oily
201 C 2H 5 C 2H 5 0 2，5-diCl-4-F-C 6H 2 H H CH 3 Oily
202 C 2H 5 C 2H 5 0 2，4，5-tri Cl-C 6H 2 H H CH 3 Oily
203 C 2H 5 C 2H 5 0 2，4，6-tri Cl-C 6H 2 H H CH 3 Oily
204 C 2H 5 C 2H 5 0 2，4，5-tri CH 3-C 6H 2 H H CH 3 Oily
205 C 2H 5 C 2H 5 0 2，4，6-tri CH 3-C 6H 2 H H CH 3 Oily
206 CH 3 CH 3 0 C 6H 5 H CH 3 CH 3 Oily
207 CH 3 CH 3 0 2-Cl-C 6H 4 H CH 3 CH 3 Oily
208 CH 3 CH 3 0 3-Cl-C 6H 4 H CH 3 CH 3 Oily
209 CH 3 CH 3 0 4-Cl-C 6H 4 H CH 3 CH 3 Oily
210 CH 3 CH 3 0 2-F-C 6H 4 H CH 3 CH 3 Oily
211 CH 3 CH 3 0 3-F-C 6H 4 H CH 3 CH 3 Oily
212 CH 3 CH 3 0 4-F-C 6H 4 H CH 3 CH 3 Oily
213 CH 3 CH 3 0 2-Br-C 6H 4 H CH 3 CH 3 Oily
214 CH 3 CH 3 0 3-Br-C 6H 4 H CH 3 CH 3 Oily
215 CH 3 CH 3 0 4-Br-C 6H 4 H CH 3 CH 3 Oily
216 CH 3 CH 3 0 2-Me-C 6H 4 H CH 3 CH 3 Oily
217 CH 3 CH 3 0 3-Me-C 6H 4 H CH 3 CH 3 Oily
218 CH 3 CH 3 0 4-Me-C 6H 4 H CH 3 CH 3 Oily
219 CH 3 CH 3 0 2-CF 3-C 6H 4 H CH 3 CH 3 Oily
220 CH 3 CH 3 0 3-CF 3-C 6H 4 H CH 3 CH 3 Oily
221 CH 3 CH 3 0 4-CF 3-C 6H 4 H CH 3 CH 3 Oily
222 CH 3 CH 3 0 2-MeO-C 6H 4 H CH 3 CH 3 Oily
223 CH 3 CH 3 0 3-MeO-C 6H 4 H CH 3 CH 3 Oily
224 CH 3 CH 3 0 4-MeO-C 6H 4 H CH 3 CH 3 Oily
225 CH 3 CH 3 0 2-CF 3O-C 6H 4 H CH 3 CH 3 Oily
226 CH 3 CH 3 0 3-CF 3O-C 6H 4 H CH 3 CH 3 Oily
227 CH 3 CH 3 0 4-CF 3O-C 6H 4 H CH 3 CH 3 Oily
228 CH 3 CH 3 0 4-F 2CHO-C 6H 4 H CH 3 CH 3 Oily
229 CH 3 CH 3 0 The 2-pyridyl H CH 3 CH 3 Oily
230 CH 3 CH 3 0 The 3-pyridyl H CH 3 CH 3 Oily
231 CH 3 CH 3 0 The 4-pyridyl H CH 3 CH 3 Oily
232 CH 3 CH 3 0 The 3-Cl-2-pyridyl H CH 3 CH 3 Oily
233 CH 3 CH 3 0 The 4-Cl-2-pyridyl H CH 3 CH 3 Oily
234 CH 3 CH 3 0 The 4-Cl-3-pyridyl H CH 3 CH 3 Oily
235 CH 3 CH 3 0 The 5-Cl-3-pyridyl H CH 3 CH 3 Oily
236 CH 3 CH 3 0 The 3-Cl-4-pyridyl H CH 3 CH 3 Oily
237 CH 3 CH 3 0 The 1-naphthyl H CH 3 CH 3 Oily
238 CH 3 CH 3 0 2，4-diCl-C 6H 3 H CH 3 CH 3 Oily
239 CH 3 CH 3 0 2，5-diCl-C 6H 3 H CH 3 CH 3 Oily
240 CH 3 CH 3 0 3，4-diCl-C 6H 3 H CH 3 CH 3 Oily
241 CH 3 CH 3 0 2-Cl-4-Me-C 6H 3 H CH 3 CH 3 Oily
242 CH 3 CH 3 0 3-Cl-4-Me-C 6H 3 H CH 3 CH 3 Oily
243 CH 3 CH 3 0 2-F-4-Me-C 6H 3 H CH 3 CH 3 Oily
244 CH 3 CH 3 0 3-F-4-Me-C 6H 3 H CH 3 CH 3 Oily
245 CH 3 CH 3 0 2，4-diMe-C 6H 3 H CH 3 CH 3 Oily
246 CH 3 CH 3 0 2，5-diMe-C 6H 3 H CH 3 CH 3 Oily
247 CH 3 CH 3 0 3，4-diMe-C 6H 3 H CH 3 CH 3 Oily
248 CH 3 CH 3 0 2，4di(MeO)-C 6H 3 H CH 3 CH 3 Oily
249 CH 3 CH 3 0 3，4di(MeO)-C 6H 3 H CH 3 CH 3 Oily
250 CH 3 CH 3 0 3，5di(MeO)-C 6H 3 H CH 3 CH 3 Oily
251 CH 3 CH 3 0 3，5di(CF 3)-C 6H 3 H CH 3 CH 3 Oily
252 CH 3 CH 3 0 2，5-diCl-4-F-C 6H 2 H CH 3 CH 3 Oily
253 CH 3 CH 3 0 2，4，5-tri Cl-C 6H 2 H CH 3 CH 3 Oily
254 CH 3 CH 3 0 2，4，6-tri Cl-C 6H 2 H CH 3 CH 3 Oily
255 CH 3 CH 3 0 2，4，5-tri CH 3-C 6H 2 H CH 3 CH 3 Oily
256 CH 3 CH 3 0 2，4，6-tri CH 3-C 6H 2 H CH 3 CH 3 Oily
257 CH 3 CH 3 0 C 6H 5 H H C 2H 5 Oily
258 CH 3 CH 3 0 2-Cl-C 6H 4 H H C 2H 5 Oily
259 CH 3 CH 3 0 3-Cl-C 6H 4 H H C 2H 5 Oily
260 CH 3 CH 3 0 4-Cl-C 6H 4 H H C 2H 5 Oily
261 CH 3 CH 3 0 2-F-C 6H 4 H H C 2H 5 Oily
262 CH 3 CH 3 0 3-F-C 6H 4 H H C 2H 5 Oily
263 CH 3 CH 3 0 4-F-C 6H 4 H H C 2H 5 Oily
264 CH 3 CH 3 0 2-Br-C 6H 4 H H C 2H 5 Oily
265 CH 3 CH 3 0 3-Br-C 6H 4 H H C 2H 5 Oily
266 CH 3 CH 3 0 4-Br-C 6H 4 H H C 2H 5 Oily
267 CH 3 CH 3 0 2-Me-C 6H 4 H H C 2H 5 Oily
268 CH 3 CH 3 0 3-Me-C 6H 4 H H C 2H 5 Oily
269 CH 3 CH 3 0 4-Me-C 6H 4 H H C 2H 5 Oily
270 CH 3 CH 3 0 2-CF 3-C 6H 4 H H C 2H 5 Oily
271 CH 3 CH 3 0 3-CF 3-C 6H 4 H H C 2H 5 Oily
272 CH 3 CH 3 0 4-CF 3-C 6H 4 H H C 2H 5 Oily
273 CH 3 CH 3 0 2-MeO-C 6H 4 H H C 2H 5 Oily
274 CH 3 CH 3 0 3-MeO-C 6H 4 H H C 2H 5 Oily
275 CH 3 CH 3 0 4-MeO-C 6H 4 H H C 2H 5 Oily
276 CH 3 CH 3 0 2-CF 3O-C 6H 4 H H C 2H 5 Oily
277 CH 3 CH 3 0 3-CF 3O-C 6H 4 H H C 2H 5 Oily
278 CH 3 CH 3 0 4-CF 3O-C 6H 4 H H C 2H 5 Oily
279 CH 3 CH 3 0 4-F 2CHO-C 6H 4 H H C 2H 5 Oily
280 CH 3 CH 3 0 The 2-pyridyl H H C 2H 5 Oily
281 CH 3 CH 3 0 The 3-pyridyl H H C 2H 5 Oily
282 CH 3 CH 3 0 The 4-pyridyl H H C 2H 5 Oily
283 CH 3 CH 3 0 The 3-Cl-2-pyridyl H H C 2H 5 Oily
284 CH 3 CH 3 0 The 4-Cl-2-pyridyl H H C 2H 5 Oily
285 CH 3 CH 3 0 The 4-Cl-3-pyridyl H H C 2H 5 Oily
286 CH 3 CH 3 0 The 5-Cl-3-pyridyl H H C 2H 5 Oily
287 CH 3 CH 3 0 The 3-Cl-4-pyridyl H H C 2H 5 Oily
288 CH 3 CH 3 0 The 1-naphthyl H H C 2H 5 Oily
289 CH 3 CH 3 0 2，4-diCl-C 6H 3 H H C 2H 5 Oily
290 CH 3 CH 3 0 2，5-diCl-C 6H 3 H H C 2H 5 Oily
291 CH 3 CH 3 0 3，4-diCl-C 6H 3 H H C 2H 5 Oily
292 CH 3 CH 3 0 2-Cl-4-Me-C 6H 3 H H C 2H 5 Oily
293 CH 3 CH 3 0 3-Cl-4-Me-C 6H 3 H H C 2H 5 Oily
294 CH 3 CH 3 0 2-F-4-Me-C 6H 3 H H C 2H 5 Oily
295 CH 3 CH 3 0 3-F-4-Me-C 6H 3 H H C 2H 5 Oily
296 CH 3 CH 3 0 2，4-diMe-C 6H 3 H H C 2H 5 Oily
297 CH 3 CH 3 0 2，5-diMe-C 6H 3 H H C 2H 5 Oily
298 CH 3 CH 3 0 3，4-diMe-C 6H 3 H H C 2H 5 Oily
299 CH 3 CH 3 0 2，4di(MeO)-C 6H 3 H H C 2H 5 Oily
300 CH 3 CH 3 0 3，4di(MeO)-C 6H 3 H H C 2H 5 Oily
301 CH 3 CH 3 0 3，5di(MeO)-C 6H 3 H H C 2H 5 Oily
302 CH 3 CH 3 0 3，5di(CF 3)-C 6H 3 H H C 2H 5 Oily
303 CH 3 CH 3 0 2，5-diCl-4-F-C 6H 2 H H C 2H 5 Oily
304 CH 3 CH 3 0 2，4，5-tri Cl-C 6H 2 H H C 2H 5 Oily
305 CH 3 CH 3 0 2，4，6-tri Cl-C 6H 2 H H C 2H 5 Oily
306 CH 3 CH 3 0 2，4，5-tri CH 3-C 6H 2 H H C 2H 5 Oily
307 CH 3 CH 3 0 2，4，6-tri CH 3-C 6H 2 H H C 2H 5 Oily
308 CH 3 CH 3 0 C 6H 5 H CH 3 C 2H 5 Oily
309 CH 3 CH 3 0 2-Cl-C 6H 4 H CH 3 C 2H 5 Oily
310 CH 3 CH 3 0 3-Cl-C 6H 4 H CH 3 C 2H 5 Oily
311 CH 3 CH 3 0 4-Cl-C 6H 4 H CH 3 C 2H 5 Oily
312 CH 3 CH 3 0 2-F-C 6H 4 H CH 3 C 2H 5 Oily
313 CH 3 CH 3 0 3-F-C 6H 4 H CH 3 C 2H 5 Oily
314 CH 3 CH 3 0 4-F-C 6H 4 H CH 3 C 2H 5 Oily
315 CH 3 CH 3 0 2-Br-C 6H 4 H CH 3 C 2H 5 Oily
316 CH 3 CH 3 0 3-Br-C 6H 4 H CH 3 C 2H 5 Oily
317 CH 3 CH 3 0 4-Br-C 6H 4 H CH 3 C 2H 5 Oily
318 CH 3 CH 3 0 2-Me-C 6H 4 H CH 3 C 2H 5 Oily
319 CH 3 CH 3 0 3-Me-C 6H 4 H CH 3 C 2H 5 Oily
320 CH 3 CH 3 0 4-Me-C 6H 4 H CH 3 C 2H 5 Oily
321 CH 3 CH 3 0 2-CF 3-C 6H 4 H CH 3 C 2H 5 Oily
322 CH 3 CH 3 0 3-CF 3-C 6H 4 H CH 3 C 2H 5 Oily
323 CH 3 CH 3 0 4-CF 3-C 6H 4 H CH 3 C 2H 5 Oily
324 CH 3 CH 3 0 2-MeO-C 6H 4 H CH 3 C 2H 5 Oily
325 CH 3 CH 3 0 3-MeO-C 6H 4 H CH 3 C 2H 5 Oily
326 CH 3 CH 3 0 4-MeO-C 6H 4 H CH 3 C 2H 5 Oily
327 CH 3 CH 3 0 2-CF 3O-C 6H 4 H CH 3 C 2H 5 Oily
328 CH 3 CH 3 0 3-CF 3O-C 6H 4 H CH 3 C 2H 5 Oily
329 CH 3 CH 3 0 4-CF 3O-C 6H 4 H CH 3 C 2H 5 Oily
330 CH 3 CH 3 0 4-F 2CHO-C 6H 4 H CH 3 C 2H 5 Oily
331 CH 3 CH 3 0 The 2-pyridyl H CH 3 C 2H 5 Oily
332 CH 3 CH 3 0 The 3-pyridyl H CH 3 C 2H 5 Oily
333 CH 3 CH 3 0 The 4-pyridyl H CH 3 C 2H 5 Oily
334 CH 3 CH 3 0 The 3-Cl-2-pyridyl H CH 3 C 2H 5 Oily
335 CH 3 CH 3 0 The 4-Cl-2-pyridyl H CH 3 C 2H 5 Oily
336 CH 3 CH 3 0 The 4-Cl-3-pyridyl H CH 3 C 2H 5 Oily
337 CH 3 CH 3 0 The 5-Cl-3-pyridyl H CH 3 C 2H 5 Oily
338 CH 3 CH 3 0 The 3-Cl-4-pyridyl H CH 3 C 2H 5 Oily
339 CH 3 CH 3 0 The 1-naphthyl H CH 3 C 2H 5 Oily
340 CH 3 CH 3 0 2，4-diCl-C 6H 3 H CH 3 C 2H 5 Oily
341 CH 3 CH 3 0 2，5-diCl-C 6H 3 H CH 3 C 2H 5 Oily
342 CH 3 CH 3 0 3，4-diCl-C 6H 3 H CH 3 C 2H 5 Oily
343 CH 3 CH 3 0 2-Cl-4-Me-C 6H 3 H CH 3 C 2H 5 Oily
344 CH 3 CH 3 0 3-Cl-4-Me-C 6H 3 H CH 3 C 2H 5 Oily
345 CH 3 CH 3 0 2-F-4-Me-C 6H 3 H CH 3 C 2H 5 Oily
346 CH 3 CH 3 0 3-F-4-Me-C 6H 3 H CH 3 C 2H 5 Oily
347 CH 3 CH 3 0 2，4-diMe-C 6H 3 H CH 3 C 2H 5 Oily
348 CH 3 CH 3 0 2，5-diMe-C 6H 3 H CH 3 C 2H 5 Oily
349 CH 3 CH 3 0 3，4-diMe-C 6H 3 H CH 3 C 2H 5 Oily
350 CH 3 CH 3 0 2，4di(MeO)-C 6H 3 H CH 3 C 2H 5 Oily
351 CH 3 CH 3 0 3，4di(MeO)-C 6H 3 H CH 3 C 2H 5 Oily
352 CH 3 CH 3 0 3，5di(MeO)-C 6H 3 H CH 3 C 2H 5 Oily
353 CH 3 CH 3 0 3，5di(CF 3)-C 6H 3 H CH 3 C 2H 5 Oily
354 CH 3 CH 3 0 2，5-diCl-4-F-C 6H 2 H CH 3 C 2H 5 Oily
355 CH 3 CH 3 0 2，4，5-tri Cl-C 6H 2 H CH 3 C 2H 5 Oily
356 CH 3 CH 3 0 2，4，6-tri Cl-C 6H 2 H CH 3 C 2H 5 Oily
357 CH 3 CH 3 0 2，4，5-tri CH 3-C 6H 2 H CH 3 C 2H 5 Oily
358 CH 3 CH 3 0 2，4，6-tri CH 3-C 6H 2 H CH 3 C 2H 5 Oily
359 C 2H 5 CH 3 0 C 6H 5 H CH 3 C 2H 5 Oily
360 C 2H 5 CH 3 0 2-Cl-C 6H 4 H CH 3 C 2H 5 Oily
361 C 2H 5 CH 3 0 3-Cl-C 6H 4 H CH 3 C 2H 5 Oily
362 C 2H 5 CH 3 0 4-Cl-C 6H 4 H CH 3 C 2H 5 Oily
363 C 2H 5 CH 3 0 2-F-C 6H 4 H CH 3 C 2H 5 Oily
364 C 2H 5 CH 3 0 3-F-C 6H 4 H CH 3 C 2H 5 Oily
365 C 2H 5 CH 3 0 4-F-C 6H 4 H CH 3 C 2H 5 Oily
366 C 2H 5 CH 3 0 2-Br-C 6H 4 H CH 3 C 2H 5 Oily
367 C 2H 5 CH 3 0 3-Br-C 6H 4 H CH 3 C 2H 5 Oily
368 C 2H 5 CH 3 0 4-Br-C 6H 4 H CH 3 C 2H 5 Oily
369 C 2H 5 CH 3 0 2-Me-C 6H 4 H CH 3 C 2H 5 Oily
370 C 2H 5 CH 3 0 3-Me-C 6H 4 H CH 3 C 2H 5 Oily
371 C 2H 5 CH 3 0 4-Me-C 6H 4 H CH 3 C 2H 5 Oily
372 C 2H 5 CH 3 0 2-CF 3-C 6H 4 H CH 3 C 2H 5 Oily
373 C 2H 5 CH 3 0 3-CF 3-C 6H 4 H CH 3 C 2H 5 Oily
374 C 2H 5 CH 3 0 4-CF 3-C 6H 4 H CH 3 C 2H 5 Oily
375 C 2H 5 CH 3 0 2-MeO-C 6H 4 H CH 3 C 2H 5 Oily
376 C 2H 5 CH 3 0 3-MeO-C 6H 4 H CH 3 C 2H 5 Oily
377 C 2H 5 CH 3 0 4-MeO-C 6H 4 H CH 3 C 2H 5 Oily
378 C 2H 5 CH 3 0 2-CF 3O-C 6H 4 H CH 3 C 2H 5 Oily
379 C 2H 5 CH 3 0 3-CF 3O-C 6H 4 H CH 3 C 2H 5 Oily
380 C 2H 5 CH 3 0 4-CF 3O-C 6H 4 H CH 3 C 2H 5 Oily
381 C 2H 5 CH 3 0 4-F 2CHO-C 6H 4 H CH 3 C 2H 5 Oily
382 C 2H 5 CH 3 0 The 2-pyridyl H CH 3 C 2H 5 Oily
383 C 2H 5 CH 3 0 The 3-pyridyl H CH 3 C 2H 5 Oily
384 C 2H 5 CH 3 0 The 4-pyridyl H CH 3 C 2H 5 Oily
385 C 2H 5 CH 3 0 The 3-Cl-2-pyridyl H CH 3 C 2H 5 Oily
386 C 2H 5 CH 3 0 The 4-Cl-2-pyridyl H CH 3 C 2H 5 Oily
387 C 2H 5 CH 3 0 The 4-Cl-3-pyridyl H CH 3 C 2H 5 Oily
388 C 2H 5 CH 3 0 The 5-Cl-3-pyridyl H CH 3 C 2H 5 Oily
389 C 2H 5 CH 3 0 The 3-Cl-4-pyridyl H CH 3 C 2H 5 Oily
390 C 2H 5 CH 3 0 The 1-naphthyl H CH 3 C 2H 5 Oily
391 C 2H 5 CH 3 0 2，4-diCl-C 6H 3 H CH 3 C 2H 5 Oily
392 C 2H 5 CH 3 0 2，5-diCl-C 6H 3 H CH 3 C 2H 5 Oily
393 C 2H 5 CH 3 0 3，4-diCl-C 6H 3 H CH 3 C 2H 5 Oily
394 C 2H 5 CH 3 0 2-Cl-4-Me-C 6H 3 H CH 3 C 2H 5 Oily
395 C 2H 5 CH 3 0 3-Cl-4-Me-C 6H 3 H CH 3 C 2H 5 Oily
396 C 2H 5 CH 3 0 2-F-4-Me-C 6H 3 H CH 3 C 2H 5 Oily
397 C 2H 5 CH 3 0 3-F-4-Me-C 6H 3 H CH 3 C 2H 5 Oily
398 C 2H 5 CH 3 0 2，4-diMe-C 6H 3 H CH 3 C 2H 5 Oily
399 C 2H 5 CH 3 0 2，5-diMe-C 6H 3 H CH 3 C 2H 5 Oily
400 C 2H 5 CH 3 0 3，4-diMe-C 6H 3 H CH 3 C 2H 5 Oily
401 C 2H 5 CH 3 0 2，4di(MeO)-C 6H 3 H CH 3 C 2H 5 Oily
402 C 2H 5 CH 3 0 3，4di(MeO)-C 6H 3 H CH 3 C 2H 5 Oily
403 C 2H 5 CH 3 0 3，5di(MeO)-C 6H 3 H CH 3 C 2H 5 Oily
404 C 2H 5 CH 3 0 3，5di(CF 3)-C 6H 3 H CH 3 C 2H 5 Oily
405 C 2H 5 CH 3 0 2，5-diCl-4-F-C6H2 H CH 3 C 2H 5 Oily
406 C 2H 5 CH 3 0 2，4，5-tri Cl-C 6H 2 H CH 3 C 2H 5 Oily
407 C 2H 5 CH 3 0 2，4，6-tri Cl-C 6H 2 H CH 3 C 2H 5 Oily
408 C 2H 5 CH 3 0 2，4，5-tri CH 3-C 6H 2 H CH 3 C 2H 5 Oily
409 C 2H 5 CH 3 0 2，4，6-tri CH 3-C 6H 2 H CH 3 C 2H 5 Oily
410 CH 3 CH 3 1 C 6H 5 H H CH 3 Oily
411 CH 3 CH 3 1 2-Cl-C 6H 4 H H CH 3 Oily
412 CH 3 CH 3 1 3-Cl-C 6H 4 H H CH 3 Oily
413 CH 3 CH 3 1 4-Cl-C 6H 4 H H CH 3 Oily
414 CH 3 CH 3 1 2-F-C 6H 4 H H CH 3 Oily
415 CH 3 CH 3 1 3-F-C 6H 4 H H CH 3 Oily
416 CH 3 CH 3 1 4-F-C 6H 4 H H CH 3 Oily
417 CH 3 CH 3 1 2-Br-C 6H 4 H H CH 3 Oily
418 CH 3 CH 3 1 3-Br-C 6H 4 H H CH 3 Oily
419 CH 3 CH 3 1 4-Br-C 6H 4 H H CH 3 Oily
420 CH 3 CH 3 1 2-Me-C 6H 4 H H CH 3 Oily
421 CH 3 CH 3 1 3-Me-C 6H 4 H H CH 3 Oily
422 CH 3 CH 3 1 4-Me-C 6H 4 H H CH 3 Oily
423 CH 3 CH 3 1 2-CF 3-C 6H 4 H H CH 3 Oily
424 CH 3 CH 3 1 3-CF 3-C 6H 4 H H CH 3 Oily
425 CH 3 CH 3 1 4-CF 3-C 6H 4 H H CH 3 Oily
426 CH 3 CH 3 1 2-MeO-C 6H 4 H H CH 3 Oily
427 CH 3 CH 3 1 3-MeO-C 6H 4 H H CH 3 Oily
428 CH 3 CH 3 1 4-MeO-C 6H 4 H H CH 3 Oily
429 CH 3 CH 3 1 2-CF 3O-C 6H 4 H H CH 3 Oily
430 CH 3 CH 3 1 3-CF 3O-C 6H 4 H H CH 3 Oily
431 CH 3 CH 3 1 4-CF 3O-C 6H 4 H H CH 3 Oily
432 CH 3 CH 3 1 4-F 2CHO-C 6H 4 H H CH 3 Oily
433 CH 3 CH 3 1 The 2-pyridyl H H CH 3 Oily
434 CH 3 CH 3 1 The 3-pyridyl H H CH 3 Oily
435 CH 3 CH 3 1 The 4-pyridyl H H CH 3 Oily
436 CH 3 CH 3 1 The 3-Cl-2-pyridyl H H CH 3 Oily
437 CH 3 CH 3 1 The 4-Cl-2-pyridyl H H CH 3 Oily
438 CH 3 CH 3 1 The 4-Cl-3-pyridyl H H CH 3 Oily
439 CH 3 CH 3 1 The 5-Cl-3-pyridyl H H CH 3 Oily
440 CH 3 CH 3 1 The 3-Cl-4-pyridyl H H CH 3 Oily
441 CH 3 CH 3 1 The 1-naphthyl H H CH 3 Oily
442 CH 3 CH 3 1 2，4-diCl-C 6H 3 H H CH 3 Oily
443 CH 3 CH 3 1 2，5-diCl-C 6H 3 H H CH 3 Oily
444 CH 3 CH 3 1 3，4-diCl-C 6H 3 H H CH 3 Oily
445 CH 3 CH 3 1 2-Cl-4-Me-C 6H 3 H H CH 3 Oily
446 CH 3 CH 3 1 3-Cl-4-Me-C 6H 3 H H CH 3 Oily
447 CH 3 CH 3 1 2-F-4-Me-C 6H 3 H H CH 3 Oily
448 CH 3 CH 3 1 3-F-4-Me-C 6H 3 H H CH 3 Oily
449 CH 3 CH 3 1 2，4-diMe-C 6H 3 H H CH 3 Oily
450 CH 3 CH 3 1 2，5-diMe-C 6H 3 H H CH 3 Oily
451 CH 3 CH 3 1 3，4-diMe-C 6H 3 H H CH 3 Oily
452 CH 3 CH 3 1 2，4di(MeO)-C 6H 3 H H CH 3 Oily
453 CH 3 CH 3 1 3，4di(MeO)-C 6H 3 H H CH 3 Oily
454 CH 3 CH 3 1 3，5di(MeO)-C 6H 3 H H CH 3 Oily
455 CH 3 CH 3 1 3，5di(CF 3)-C 6H 3 H H CH 3 Oily
456 CH 3 CH 3 1 2，5-diCl-4-F-C 6H 2 H H CH 3 Oily
457 CH 3 CH 3 1 2，4，5-tri Cl-C 6H 2 H H CH 3 Oily
458 CH 3 CH 3 1 2，4，6-tri Cl-C 6H 2 H H CH 3 Oily
459 CH 3 CH 3 1 2，4，5-tri CH 3-C 6H 2 H H CH 3 Oily
460 CH 3 CH 3 1 2，4，6-tri CH 3-C 6H 2 H H CH 3 Oily
461 CH3 C 2H 5 0 C 6H 5 H CH 3 C 2H 5 Oily
462 CH3 C 2H 5 0 2-Cl-C 6H 4 H CH 3 C 2H 5 Oily
463 CH3 C 2H 5 0 3-Cl-C 6H 4 H CH 3 C 2H 5 Oily
464 CH3 C 2H 5 0 4-Cl-C 6H 4 H CH 3 C 2H 5 Oily
465 CH3 C 2H 5 0 2-F-C 6H 4 H CH 3 C 2H 5 Oily
466 CH3 C 2H 5 0 3-F-C 6H 4 H CH 3 C 2H 5 Oily
467 CH3 C 2H 5 0 4-F-C 6H 4 H CH 3 C 2H 5 Oily
468 CH3 C 2H 5 0 2-Br-C 6H 4 H CH 3 C 2H 5 Oily
469 CH3 C 2H 5 0 3-Br-C 6H 4 H CH 3 C 2H 5 Oily
470 CH3 C 2H 5 0 4-Br-C 6H 4 H CH 3 C 2H 5 Oily
471 CH3 C 2H 5 0 2-Me-C 6H 4 H CH 3 C 2H 5 Oily
472 CH3 C 2H 5 0 3-Me-C 6H 4 H CH 3 C 2H 5 Oily
473 CH3 C 2H 5 0 4-Me-C 6H 4 H CH 3 C 2H 5 Oily
474 CH3 C 2H 5 0 2-CF 3-C 6H 4 H CH 3 C 2H 5 Oily
475 CH3 C 2H 5 0 3-CF 3-C 6H 4 H CH 3 C 2H 5 Oily
476 CH3 C 2H 5 0 4-CF 3-C 6H 4 H CH 3 C 2H 5 Oily
477 CH3 C 2H 5 0 2-MeO-C 6H 4 H CH 3 C 2H 5 Oily
478 CH3 C 2H 5 0 3-MeO-C 6H 4 H CH 3 C 2H 5 Oily
479 CH3 C 2H 5 0 4-MeO-C 6H 4 H CH 3 C 2H 5 Oily
480 CH3 C 2H 5 0 2-CF 3O-C 6H 4 H CH 3 C 2H 5 Oily
481 CH3 C 2H 5 0 3-CF 3O-C 6H 4 H CH 3 C 2H 5 Oily
482 CH3 C 2H 5 0 4-CF 3O-C 6H 4 H CH 3 C 2H 5 Oily
483 CH3 C 2H 5 0 4-F 2CHO-C 6H 4 H CH 3 C 2H 5 Oily
484 CH3 C 2H 5 0 The 2-pyridyl H CH 3 C 2H 5 Oily
485 CH3 C 2H 5 0 The 3-pyridyl H CH 3 C 2H 5 Oily
486 CH3 C 2H 5 0 The 4-pyridyl H CH 3 C 2H 5 Oily
487 CH3 C 2H 5 0 The 3-Cl-2-pyridyl H CH 3 C 2H 5 Oily
488 CH3 C 2H 5 0 The 4-Cl-2-pyridyl H CH 3 C 2H 5 Oily
489 CH3 C 2H 5 0 The 4-Cl-3-pyridyl H CH 3 C 2H 5 Oily
490 CH3 C 2H 5 0 The 5-Cl-3-pyridyl H CH 3 C 2H 5 Oily
491 CH3 C 2H 5 0 The 3-Cl-4-pyridyl H CH 3 C 2H 5 Oily
492 CH3 C 2H 5 0 The 1-naphthyl H CH 3 C 2H 5 Oily
493 CH3 C 2H 5 0 2，4-diCl-C 6H 3 H CH 3 C 2H 5 Oily
494 CH3 C 2H 5 0 2，5-diCl-C 6H 3 H CH 3 C 2H 5 Oily
495 CH3 C 2H 5 0 3，4-diCl-C 6H 3 H CH 3 C 2H 5 Oily
496 CH3 C 2H 5 0 2-Cl-4-Me-C 6H 3 H CH 3 C 2H 5 Oily
497 CH3 C 2H 5 0 3-Cl-4-Me-C 6H 3 H CH 3 C 2H 5 Oily
498 CH3 C 2H 5 0 2-F-4-Me-C 6H 3 H CH 3 C 2H 5 Oily
499 CH3 C 2H 5 0 3-F-4-Me-C 6H 3 H CH 3 C 2H 5 Oily
500 CH3 C 2H 5 0 2，4-diMe-C 6H 3 H CH 3 C 2H 5 Oily
501 CH3 C 2H 5 0 2，5-diMe-C 6H 3 H CH 3 C 2H 5 Oily
502 CH3 C 2H 5 0 3，4-diMe-C 6H 3 H CH 3 C 2H 5 Oily
503 CH3 C 2H 5 0 2，4di(MeO)-C 6H 3 H CH 3 C 2H 5 Oily
504 CH3 C 2H 5 0 3，4di(MeO)-C 6H 3 H CH 3 C 2H 5 Oily
505 CH3 C 2H 5 0 3，5di(MeO)-C 6H 3 H CH 3 C 2H 5 Oily
506 CH3 C 2H 5 0 3，5di(CF 3)-C 6H 3 H CH 3 C 2H 5 Oily
507 CH3 C 2H 5 0 2，5-diCl-4-F-C 6H 2 H CH 3 C 2H 5 Oily
508 CH3 C 2H 5 0 2，4，5-tri Cl-C 6H 2 H CH 3 C 2H 5 Oily
509 CH3 C 2H 5 0 2，4，6-tri Cl-C 6H 2 H CH 3 C 2H 5 Oily
600 CH3 C 2H 5 0 2，4，5-tri CH 3-C 6H 2 H CH 3 C 2H 5 Oily
601 CH3 C 2H 5 0 2，4，6-tri CH 3-C 6H 2 H CH 3 C 2H 5 Oily
During n=0, formula (I) compound can prepare R in the formula by following reaction in the general formula of the present invention (I) 1, R 2, R 3, R 4, R 5, R 6Definition the same; Z is leavings group such as halogen (chlorine, bromine or iodine).
Reaction formula is:
The concrete preparation method of formula (I) compound: at CH 2Cl 2, THF, in DMF or the DMSO equal solvent, with formula (II) compound and formula (III) compound react under the alkaline condition and under-10 ℃～30 ℃ temperature of reaction formula (I) compound.Used alkali is alkaline carbonate or supercarbonate, alkaline earth metal carbonate or supercarbonate, alkali metal hydroxide or alkaline earth metal hydroxides, NaH, NH 2Na, tertiary butyl potassium, tertiary butyl sodium etc.; More than preferred alkali be K 2CO 3, Na 2CO 3, NaOH, KOH, NaH or NaNH 2
In general formula of the present invention (I), when n=1 or 2, its preparation method is: with formula (I) compound and the H of n=0 2O 2Or the Sodium peroxoborate reaction promptly gets formula (I) compound of n=1 or 2, R in the formula 1, R 2, R 3, R 4, R 5, R 6Definition the same; Z is leavings group such as halogen (chlorine, bromine or iodine).The preferred solvent of above-mentioned reaction is THF, DMF or DMSO; Preferred temperature of reaction is 10 ℃～60 ℃.
Organic Synthesis Collective Volume III, p.668,1955 and European patent EP 0619301A 2In, the synthetic method of formula (II) compound of Z=Br has been described.
European patent EP 1125931 has been described the synthetic method of formula (III) compound.
Formula (I) compound can be prevented and treated by multiple fungus-caused diseases such as Phycomycetes, Oomycete, Ascomycetes, Basidiomycetes and deuteromycetes, and they have systemic activity and can be used as the blade face and soil mycocide.Be specially adapted to prevent and treat rice blast; Rust on the stripe rust of barley and wheat, leaf rust, black rust and other crops; Powdery Mildew on cucurbits powdery mildew, apple mildew, uncinula necator and other plant on the ground family crops such as the Powdery Mildew of barley and wheat, cucumber, muskmelon, sponge gourd, pumpkin; Wheat hypochnus and glume blight; Helminthosporium on the cereal, the mouth spore is mould, Septoria is sick, the caryosphere shell belong to sick, pseudo-cercospora is sick, the top softgel shell belongs to sick; The cercospora black spot of peanut that the cercospora brown spot of peanut that Semen arachidis hypogaeae tail spore causes and ball seat tail spore cause; Other Cercospora disease on beet, soybean and the paddy; Grey mold disease on vegetables such as tomato, cucumber, grape and the fruit; Glue chain spore on the vegetables belongs to disease; Cucumber anthracnose, scab of apple; Oomycetes disease such as cucumber downy mildew, downy mildew of garpe, the late blight of potato, tomato late blight; Damping-off that thanatephorus cucumeris(frank) donk causes and banded sclerotial blight.
By in The compounds of this invention, adding other one or more mycocides, can enlarge fungicidal spectrum, and have the Synergistic sterilizing effect.Embodiment: further specify the present invention below in conjunction with embodiment.
Embodiment 1 compound (E)-N-methoxyl group-N-[2-[1--phenyl-2-methylthio group-ethyliminum oxygen methyl]-phenyl] preparation of Urethylane (compound 1)
In 20mlDMF, (the E)-1-phenyl-2-methylthio group-ethylidenehydroxylamine of adding 0.724g (4mmol) and content are 50% NaH0.24g (0.5mmol), at 20～25 ℃ of N-(2-2-bromomethylphenyl)-N-methoxyl group-Urethylanes that drip 1.4g (5.0mmol) down.Drip and finish, reaction mixture is poured in the 100ml water, ethyl acetate extraction twice merges organic layer, is washed to neutrality, anhydrous Na 2SO 4Dry.1: 3 mixed solution of ethyl acetate and sherwood oil flushing column chromatography gets title compound 0.51g, yield 34.1%.
Mass spectrometry results: 375 (M+H)
Embodiment 2 compounds (E)-N-methoxyl group-N-[2-[1-(4-methyl-phenyl)-2-methylthio group-ethyliminum oxygen methyl]-phenyl] preparation of Urethylane (compound 13)
(E)-1-p-methylphenyl-2-methylthio group-ethylidenehydroxylamine of 0.98g (5mmol) and N-(2-2-bromomethylphenyl)-N-methoxyl group-Urethylane of 1.4g (5mmol) are dissolved among the 10mlDMF under room temperature, be added dropwise in the 10mlDMF suspension of 0.24gNaH (purity 50%) under 0～5 ℃ of the temperature control, have a large amount of bubbles to produce.Drip and finish, reaction mixture is poured in the 100ml water, ethyl acetate extraction twice merges organic layer, is washed to neutrality, anhydrous Na 2SO 4Dry.1: 3 mixed solution of ethyl acetate and sherwood oil flushing column chromatography gets title compound 0.87g, yield 44.8%.
Mass spectrometry results: 389 (M+H)
Embodiment 3 compounds (E)-N-methoxyl group-N-[2-[1-(3-trifluoromethyl-phenyl)-2-methylthio group-ethyliminum oxygen methyl]-phenyl] preparation of Urethylane (compound 15)
In 20mlDMF, add the NaH of (E)-1-m-trifluoromethylphenyl-2-methylthio group-ethylidenehydroxylamine and 0.2460% (4.4mmol) of 0.996g (4mmol), drip N-(2-2-bromomethylphenyl)-N-methoxyl group-Urethylane down at 20～25 ℃.Drip and finish, reaction mixture is poured in the 100ml water, ethyl acetate extraction twice merges organic layer, is washed to neutrality, anhydrous Na 2SO 4Dry.1: 3 mixed solution of ethyl acetate and sherwood oil flushing column chromatography gets title compound 0.6g, yield 33.9%.
Mass spectrometry results: 443 (M+H)
4 examples of embodiment explanation (E)-N-[2-[1-thiazolyl]-2-methylthio group-ethyliminum oxygen methyl]-phenyl] preparation of Urethylane (compound 33)
In 20ml DMF, add (E)-1-(3-thiazolyl)-2-methylthio group-ethylidenehydroxylamine of 0.748g (4mmol), the NaH of 0.24g (5mmol) 50%, drip 1.20g (4.4mmol) N-(2-2-bromomethylphenyl)-N-methoxyl group-Urethylane down at 20～25 ℃.Drip and finish, at room temperature react half an hour again, reaction mixture is poured in the 100ml water, ethyl acetate extraction twice merges organic layer, is washed to neutrality, anhydrous Na 2SO 4Dry.1: 3 mixed solution of ethyl acetate and sherwood oil flushing column chromatography gets title compound 1.0g, yield 65.7%.
Mass spectrometry results: 381 (M+H)
Embodiment 5 compounds (E)-N-methoxyl group-N-[2-[1-(2,5-two chloro-phenyl)-2-methylthio group-ethyliminum oxygen methyl]-phenyl] preparation of Urethylane (compound 35)
In the 20ml anhydrous tetrahydro furan, add (E) 1-(2 of 1.25g (5mmol), 5-two chloro-phenyl)-and 2-methylthio group-ethylidenehydroxylamine and 50% NaH 0.24g, drip 1.4g (5mmol) N-(2-2-bromomethylphenyl)-N-methoxyl group-Urethylanes down at 20～25 ℃.At room temperature stirred 0.5～1 hour afterwards, reaction solution is poured in the 100ml water again, with ethyl acetate extraction twice, merges organic layer, uses anhydrous Na 2SO 4Dry.1: 3 mixed solution of ethyl acetate and sherwood oil flushing column chromatography gets title compound 1.3g, yield 58.8%.
Mass spectrometry results: 443 (M+H)
Embodiment 6 (E)-N-methoxyl group-N-[2-[1-(2-chloro-4-methyl-phenyl)-2-methylthio group-ethyliminum oxygen methyl]-phenyl] preparation of Urethylane (compound 37)
1-(2-chloro-4-methyl-phenyl)-2-methylthio group-ethylidenehydroxylamine of 0.916g (4mmol) and N-(2-2-bromomethylphenyl)-N-methoxyl group-Urethylane of 1.21g (4.4mmol) are dissolved among the 10mlDMF under room temperature, under 0～5 ℃, be added dropwise in the 10mlDMF suspension of 0.5gNaH (purity 50%), have a large amount of bubbles to produce.Drip and finish, reaction mixture is poured in the 100ml water, ethyl acetate extraction twice merges organic layer, is washed to neutrality, anhydrous Na 2SO 4Dry.1: 3 mixed solution of ethyl acetate and sherwood oil flushing column chromatography gets title compound 0.40g, yield 23.7%.
Mass spectrometry results: 423 (M+H)
Embodiment 7 (E)-N-methoxyl group-N-[2-[1-(2,5-two chloro-4-fluoro-phenyl)-2-methylthio group-ethyliminum oxygen methyl]-phenyl] preparation of Urethylane (compound 48)
(the E)-1-(2 that in 20mlDMF, adds 1.07g (4mmol), 4-two chloro-5-fluoro-phenyl)-N-(2-2-bromomethylphenyl)-N-methoxyl group-Urethylane of 2-methylthio group-ethylidenehydroxylamine and 1.21g (4.4mmol), under 0～5 ℃, be added dropwise in the 10mlDMF suspension of 0.5gNaH (purity 50%), have a large amount of bubbles to produce.Drip and finish, reaction mixture is poured in the 100ml water, ethyl acetate extraction twice merges organic layer, is washed to neutrality, anhydrous Na 2SO 4Dry.1: 3 mixed solution of ethyl acetate and sherwood oil flushing column chromatography gets title compound 0.45g, yield 24.5%.
Mass spectrometry results: 461 (M+H)
Embodiment 8 (E)-N-oxyethyl group-N-[2-[1-(4-chloro-phenyl)-2-methylthio group-ethyliminum oxygen methyl]-phenyl] preparation of Urethylane (compound 56)
In 20mlDMF, add (E)-1-(4-chloro-phenyl)-2-methylthio group-ethylidenehydroxylamine of 0.862g (4mmol) and N-(2-2-bromomethylphenyl)-N-oxyethyl group-Urethylane of 1.26g (4.4mmol), under 0～5 ℃, be added dropwise in the 10mlDMF suspension of 0.5gNaH (purity 50%), have a large amount of bubbles to produce.Drip and finish, reaction mixture is poured in the 100ml water, ethyl acetate extraction twice merges organic layer, is washed to neutrality, anhydrous Na 2SO 4Dry.1: 3 mixed solution of ethyl acetate and sherwood oil flushing column chromatography gets title compound 0.54g, yield 32.0%.
Mass spectrometry results: 423 (M+H)
Embodiment 9 (E)-N-oxyethyl group-N-[2-[1-(3-trifluoromethyl-phenyl)-2-methylthio group-ethyliminum oxygen methyl]-phenyl] preparation of Urethylane (compound 67)
The NaH of (E)-1-of 0.996g in 20mlDMF (4mmol) (3-trifluoromethyl-phenyl)-2-methylthio group-ethylidenehydroxylamine, 0.24g (5mmol) 50%, at 20～25 ℃ of N-(2-2-bromomethylphenyl)-N-oxyethyl group-Urethylanes that drip 1.26g (4.4mmol) down, drip and finish, at room temperature react half an hour again, reaction mixture is poured in the 100ml water, and ethyl acetate extraction twice merges organic layer, be washed to neutrality, anhydrous Na 2SO 4Dry.1: 3 mixed solution of ethyl acetate and sherwood oil flushing column chromatography gets title compound 1.0g, yield 54.7%.
Mass spectrometry results: 457 (M+H)
Embodiment 10 (E)-N-methoxyl group-N-[2-[1-(4-chloro-phenyl)-2-methylthio group-ethyliminum oxygen methyl]-phenyl] urethanum (compound 107) preparation
(E)-1-(4-chloro-the phenyl)-2-methylthio group-ethylidenehydroxylamine that in 20mlDMF, adds 0.862g (4mmol), (0.5gNaH purity 50%), at 20～25 ℃ of N-(2-2-bromomethylphenyl)-N-methoxyl group-urethanum that drip 1.26g (4.4mmol) down, drip to finish and at room temperature react half an hour again, afterwards reaction mixture is poured in the 100ml water, ethyl acetate extraction twice merges organic layer, be washed to neutrality, anhydrous Na 2SO 4Dry.1: 3 mixed solution of ethyl acetate and sherwood oil flushing column chromatography gets title compound 0.30g, yield 17.7%.
Mass spectrometry results: 423 (M+H)
Embodiment 11 (E)-N-methoxyl group-N-[2-[1-(4-methyl-phenyl)-2-methylthio group-ethyliminum oxygen methyl]-phenyl] preparation of urethanum (compound 116)
(E)-1-(4-methyl-phenyl)-2-methylthio group-ethylidenehydroxylamine that in 20mlDMF, adds 0.78g (4mmol), (0.5gNaH purity 50%), at 20～25 ℃ of N-(2-2-bromomethylphenyl)-N-methoxyl group-urethanum that drip 1.26g (4.4mmol) down, drip to finish and at room temperature react half an hour again, afterwards reaction mixture is poured in the 100ml water, ethyl acetate extraction twice merges organic layer, be washed to neutrality, anhydrous Na 2SO 4Dry.1: 3 mixed solution of ethyl acetate and sherwood oil flushing column chromatography gets title compound 0.45g, yield 28.0%.
Mass spectrometry results: 403 (M+H)
Embodiment 12 (E)-N-methoxyl group-N-[2-[1-(3-trifluoromethyl-phenyl)-2-methylthio group-ethyliminum oxygen methyl]-phenyl] preparation of urethanum (compound 118)
(E)-1-(3-trifluoromethyl-phenyl)-2-methylthio group-ethylidenehydroxylamine that in 20mlDMF, adds 0.996g (4mmol), (0.5gNaH purity 50%), at 20～25 ℃ of N-(2-2-bromomethylphenyl)-N-methoxyl group-urethanum that drip 1.26g (4.4mmol) down, drip to finish and at room temperature react half an hour again, afterwards reaction mixture is poured in the 100ml water, ethyl acetate extraction twice merges organic layer, be washed to neutrality, anhydrous Na 2SO 4Dry.1: 3 mixed solution of ethyl acetate and sherwood oil flushing column chromatography gets title compound 0.52g, yield 28.5%.
Mass spectrometry results: 457 (M+H)
Embodiment 13 (E)-N-methoxyl group-N-[2-[1-(3, the 4-dichlorophenyl)-2-methylthio group-ethyliminum oxygen methyl]-phenyl] preparation of urethanum (compound 138)
(the E)-1-(3 that in 20mlDMF, adds 0.996g (4mmol), the 4-dichlorophenyl)-2-methylthio group-ethylidenehydroxylamine, (0.5gNaH purity 50%), at 20～25 ℃ of N-(2-2-bromomethylphenyl)-N-methoxyl group-urethanum that drip 1.26g (4.4mmol) down, drip to finish and at room temperature react again half an hour, reaction mixture is poured in the 100ml water afterwards, twice of ethyl acetate extraction, merge organic layer, be washed to neutrality, anhydrous Na 2SO 4Dry.1: 3 mixed solution of ethyl acetate and sherwood oil flushing column chromatography gets title compound 0.63g, yield 34.5%.
Mass spectrometry results: 457 (M+H)
Embodiment 14 (E)-N-oxyethyl group--N-[2-[1-(3-trifluoromethyl-phenyl)-2-methylthio group-ethyliminum oxygen methyl]-phenyl] preparation of urethanum (compound 169)
(the E)-1-(3 that in 20mlDMF, adds 0.996g (4mmol), the 4-dichlorophenyl)-2-methylthio group-ethylidenehydroxylamine, (0.5gNaH purity 50%), at 20～25 ℃ of N-(2-2-bromomethylphenyl)-N-oxyethyl group-urethanum that drip 1.33g (4.4mmol) down, drip to finish and at room temperature react again half an hour, reaction mixture is poured in the 100ml water afterwards, twice of ethyl acetate extraction, merge organic layer, be washed to neutrality, anhydrous Na 2SO 4Dry.1: 3 mixed solution of ethyl acetate and sherwood oil flushing column chromatography gets title compound 0.72g, yield 38.3%.
Mass spectrometry results: 471 (M+H)
Embodiment 15 (E)-N-methoxyl group-N-[2-[1-phenyl-2-methylthio group-tetrahydroform oxygen methyl]-phenyl] preparation of Urethylane (compound 206)
1-phenyl-2-methylthio group-the acetoxime and the 0.5gNaH (purity 50%) that in 20mlDMF, add 0.78g (4mmol).At N-(2-the 2-bromomethylphenyl)-N-methoxyl group-Urethylane that stirs and 20～25 ℃ drip 1.21g (4.4mmol) down, drip to finish and at room temperature react again half an hour, reaction mixture is poured in the 100ml water afterwards, twice of ethyl acetate extraction, merge organic layer, be washed to neutrality, anhydrous Na 2SO 4Dry.1: 3 mixed solution of ethyl acetate and sherwood oil flushing column chromatography gets title compound 0.62g, yield 40%.
Mass spectrometry results: 389 (M+H)
Embodiment 16 (E)-N-methoxyl group-N-[2-[1-(4-chloro-phenyl)-2-methylthio group-tetrahydroform oxygen methyl]-phenyl] preparation of Urethylane (compound 209)
1-rubigan-2-methylthio group-the acetoxime, the 0.5gNaH (purity 50%) that in 20mlDMF, add 0.916g (4mmol).At 20～25 ℃ of N-(2-2-bromomethylphenyl)-N-methoxyl group-Urethylanes that drip 1.21g (4.4mmol) down, drip to finish and at room temperature react again half an hour, reaction mixture is poured in the 100ml water afterwards, twice of ethyl acetate extraction, merge organic layer, be washed to neutrality, anhydrous Na 2SO 4Dry.1: 3 mixed solution of ethyl acetate and sherwood oil flushing column chromatography gets title compound 0.53g, yield 31.4%.
Mass spectrometry results: 423 (M+H)
Embodiment 17 (E)-N-methoxyl group-N-[2-[1-(3-methyl-phenyl)-2-methylthio group-tetrahydroform oxygen methyl]-phenyl] preparation of Urethylane (compound 217)
1-(3-methyl-phenyl)-2-methylthio group-acetoxime, the 0.5gNaH (purity 50%) that in 20mlDMF, add 0.836g (4mmol).At 20～25 ℃ of N-(2-2-bromomethylphenyl)-N-methoxyl group-Urethylanes that drip 1.21g (4.4mmol) down, drip to finish and at room temperature react again half an hour, reaction mixture is poured in the 100ml water afterwards, twice of ethyl acetate extraction, merge organic layer, be washed to neutrality, anhydrous Na 2SO 4Dry.1: 3 mixed solution of ethyl acetate and sherwood oil flushing column chromatography gets title compound 0.61g, yield 37.8%.
Mass spectrometry results: 403 (M+H)
Embodiment 18 (E)-N-methoxyl group-N-[2-[1-(3-trifluoromethyl-phenyl)-2-methylthio group-tetrahydroform oxygen methyl]-phenyl] preparation of Urethylane (compound 220)
1-(3-trifluoromethyl-phenyl)-2-methylthio group-acetoxime, the 0.5gNaH (purity 50%) that in 20mlDMF, add 1.052g (4mmol).At 20～25 ℃ of N-(2-2-bromomethylphenyl)-N-methoxyl group-Urethylanes that drip 1.21g (4.4mmol) down, drip to finish and at room temperature react again half an hour, reaction mixture is poured in the 100ml water afterwards, twice of ethyl acetate extraction, merge organic layer, be washed to neutrality, anhydrous Na 2SO 4Dry.1: 3 mixed solution of ethyl acetate and sherwood oil flushing column chromatography gets title compound 0.69g, yield 37.8%.
Mass spectrometry results: 457 (M+H)
Embodiment 19 (E)-N-methoxyl group-N-[2-[1-(3, the 4-dichlorophenyl)-2-methylthio group-tetrahydroform oxygen methyl]-phenyl] preparation of Urethylane (compound 240)
1-(3, the 4-the dichlorophenyl)-2-methylthio group-acetoxime, the 0.5gNaH (purity 50%) that in 20mlDMF, add 1.05g (4mmol).At 20～25 ℃ of N-(2-2-bromomethylphenyl)-N-methoxyl group-Urethylanes that drip 1.21g (4.4mmol) down, drip to finish and at room temperature react again half an hour, reaction mixture is poured in the 100ml water afterwards, twice of ethyl acetate extraction, merge organic layer, be washed to neutrality, anhydrous Na 2SO 4Dry.1: 3 mixed solution of ethyl acetate and sherwood oil flushing column chromatography gets title compound 0.83g, yield 45.5%.
Mass spectrometry results: 457 (M+H)
Embodiment 20 (E)-N-methoxyl group-N-[2-[1-(2-chloro-4-aminomethyl phenyl)-2-methylthio group-tetrahydroform oxygen methyl]-phenyl] preparation of Urethylane (compound 241)
1-(2-chloro-4-the aminomethyl phenyl)-2-methylthio group-acetoxime, the 0.5gNaH (purity 50%) that in 20mlDMF, add 0.97g (4mmol).At 20～25 ℃ of N-(2-2-bromomethylphenyl)-N-methoxyl group-Urethylanes that drip 1.21g (4.4mmol) down, drip to finish and at room temperature react again half an hour, reaction mixture is poured in the 100ml water afterwards, twice of ethyl acetate extraction, merge organic layer, be washed to neutrality, anhydrous Na 2SO 4Dry.1: 3 mixed solution of ethyl acetate and sherwood oil flushing column chromatography gets title compound 0.73g, yield 41.9%.Mass spectrometry results: 437 (M+H)
21 examples of embodiment explanation (E)-N-methoxyl group-N-[2-[1-(3-trifluoromethyl)-2-methylsulfinyl-ethyliminum oxygen methyl]-phenyl] preparation of Urethylane (compound 424)
With 0.442g (1.0mmol) (E)-N-methoxyl group-N-[2-[1-(3-trifluoromethyl-phenyl)-2-methylthio group-ethyliminum oxygen methyl]-phenyl] Urethylane (compound 15) is dissolved in 10mlCH 3Among the OH, add H 2O 20.34g (concentration 30%) and 2ml Glacial acetic acid stirred 2 hours under room temperature.Reaction mixture is poured in the 50ml water, and ethyl acetate extraction twice merges organic layer, is washed to neutrality, anhydrous Na 2SO 4Dry.1: 2 mixed solution of ethyl acetate and sherwood oil flushing column chromatography gets title compound 0.35g, yield 76.4%.
Mass spectrometry results: 459 (M+H)
22 examples of embodiment explanation (E)-N-methoxyl group-N-[2-[1-(2, the 5-dichlorophenyl)-2-methylsulfinyl-tetrahydroform oxygen methyl]-phenyl] preparation of Urethylane (compound 443)
With 0.456g (1.0mmol) (E)-N-methoxyl group-N-[2-[1-(2, the 5-dichlorophenyl)-2-methylthio group-tetrahydroform oxygen methyl]-phenyl] Urethylane (compound 235) is dissolved in 10mlCH 3Among the OH, add H 2O 20.34g (concentration 30%) and 2ml Glacial acetic acid stirred 2 hours under room temperature.Reaction mixture is poured in the 50ml water, and ethyl acetate extraction twice merges organic layer, is washed to neutrality, anhydrous Na 2SO 4Dry.1: 2 mixed solution of ethyl acetate and sherwood oil flushing column chromatography gets title compound 0.29g, yield 61.5%.
Mass spectrometry results: 473 (M+H)
As follows with formula of the present invention (I) compound to the test of the various fungal diseases of plant:
At greenhouse pot culture plant examination material, it is standby to grow to the certain period.To have general formula (I) compound small amount of N, the dinethylformamide dissolving is diluted with water to desired concn, and preparation is diluted with water to desired concn.Plant examination material being carried out spray pesticide handle, is contrast with spray clear water plant examination material, plant is tried material placement ventilation make the plant surface soup air-dry, inoculates pathogenic bacteria after 24 hours.Inoculation finishes, and plant is placed in the fixed temperature and humidity incubator, makes pathogenic bacteria be continued to infect.A couple of days is carried out the disease index investigation of each chemicals treatment after the inoculation when contrast is fully fallen ill.
Active classification sees Table 2:
The A level: preventive effect is 90%-100%, the B level: preventive effect is 70%-90%, the C level: preventive effect is 50-90%, the D level: preventive effect is below 50%.
Table 2: partial test result (testing compound concentration is 100ppm):
Compound number Gray mold of cucumber Cucumber downy mildew Rice sheath blight disease Rice blast Wheat powdery mildew Wheat glume blight Wheat rust Cucumber anthracnose Tomato late blight
1 B B C B A C A B B
13 B B B B A B C B B
15 A A B A A A A B A
36 B B B A A B A B B
39 A B B A B B A B B
47 A B C A A B B B B
105 B B B B A B A B B
114 B C B A B A B C B
116 B A B A A A A B B
202 B A B C A B B B C
216 A B B B A B A B A
237 B B B B A B A B B
416 B B B B A A A B B
436 B B B A B A B B B
The present invention can make up the Synergistic sterilizing effect with following sterilant: alkene azoles alcohol, nitrile bacterium azoles, the spirit of powder rust, F-1991, thiabendazole, derosal, thiophanate methyl, m-tetrachlorophthalodinitrile, Bordeaux mixture, the hot salt of biguanides, jingganmycin, hymexazol, Sukeling, Fujione, kasugamycin, zinc manganese ethylenebisdithiocarbamate, maneb, zineb, Polyoxin, propineb, thiram, tridemorph, dimethomorph, metaxanin etc.

Claims (5)

1, a kind of N-substituted-phenyl amino formate compounds with fungicidal activity, the compound shown in (I) that it is characterized in that having general formula and because the two keys of carbon-nitrogen connect Z type and the E type geometrical isomer that different substituting groups forms,
Figure C031247950002C1
In the general formula (I): R 1, R 2, R 6It is alkyl; R 4, R 5It is respectively hydrogen or alkyl; R 3Be the aryl of replacement or the heteroaryl of replacement; N is 0 or 1.
2, the preparation method with the compound shown in the general formula (I) according to claim 1 is characterized in that: when n=0, use formula (II) compound and formula (III) compound to react under alkaline condition and promptly get formula (I) compound; Used alkali is alkaline carbonate or supercarbonate, alkaline earth metal carbonate or supercarbonate, alkali metal hydroxide or alkaline earth metal hydroxides, NaH, NH 2Na, tertiary butyl potassium, tertiary butyl sodium; The solvent that is adopted has methylene dichloride, tetrahydrofuran (THF), dimethyl formamide or dimethyl sulfoxide (DMSO); Temperature of reaction is-10 ℃～30 ℃, and reaction formula is as follows:
R in the formula 1, R 2, R 3, R 4, R 5And R 6Has the above-mentioned definition of giving; Z is chlorine, bromine or iodine leavings group.
3, the preparation method with the compound shown in the general formula (I) according to claim 1 is characterized in that: when n=1, with formula (I) compound and the H of n=0 2O 2Or the Sodium peroxoborate reaction promptly gets formula (I) compound of n=1.
4, the purposes with the compound shown in the general formula (I) according to claim 1 is characterized in that: be used for preventing and treating on various crops by the multiple fungus-caused disease of Phycomycetes, Oomycete, Ascomycetes, Basidiomycetes and deuteromycetes.
5, the purposes with the compound shown in the general formula (I) according to claim 1 is characterized in that: make up with the Synergistic sterilizing effect with alkene azoles alcohol, nitrile bacterium azoles, the spirit of powder rust, F-1991, thiabendazole, derosal, thiophanate methyl, m-tetrachlorophthalodinitrile, Bordeaux mixture, the hot salt of biguanides, jingganmycin, hymexazol, Sukeling, Fujione, kasugamycin, zinc manganese ethylenebisdithiocarbamate, maneb, zineb, Polyoxin, propineb, thiram, tridemorph, dimethomorph, metaxanin.
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