Bicyclic amines

Details Bicyclic amines Bicyclic amines

2002-04-12

2003-06-03

Raymond, Richard L. (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C546S124000

Reexamination Certificate

active

06573275

ABSTRACT:

This invention relates to novel bicyclic amines, to processes for preparing them, to insecticidal compositions comprising and to methods of combatting and controlling insect pests therewith.
The invention provides compounds of formula (I) wherein R
1
represents a group of formula (A) where each of W, X, Y and Z and Z represents either a group CR or the nitrogen atom, provided that not more than two of W, X, Y and Z represent the nitrogen atom and where each R present is independently selected from hydrogen and halogen atoms and cyano, amino, hydrazino, acylamino, hydroxy, alkyl, hydroxyalkyl, alkoxy, haloalkyl, haloalkoxy, alkenyl, alkenyloxy, alkoxyalkenyl, alkynyl, carboxylic acyl, alkoxycarbonyl, aryl and heterocyclyl groups, said groups comprising up to 6 carbon atoms, and wherein R
2
represents hydrogen or cyano or a group selected from alkyl, aryl, heteroaryl, aralkyl, heteroarylalkyl, alkenyl, aralkenyl, alkynyl, alkoxycarbonyl, alkanesulfonyl, arenesulfonyl, alkanyloxycarbonyl, aralkyloxycarbonyl, aryloxycarbonyl, heterocyclylalkyl, carbamyl or dithiocarboxyl groups, said groups comprising from 1 to 15 carbon atoms, said groups being optionally substituted with one or more substituents selected from, halogen, cyano, carboxyl, carboxylic acyl, carbamyl, alkoxycarbonyl, alkoxy, alkylenedioxy, hydroxy, nitro, haloalkyl, alkyl, amino, acylamino, imidate and phosphonato groups; and acid addition salts and quaternary ammonium salts and N-oxides derived therefrom. R
1
is preferably a halo-substituted phenyl, pyridyl or diazinyl group.
In a preferred aspect invention provides compounds of formula (I) where R
1
represents an optionally halogen substituted phenyl group or an optionally halogen substituted pyridyl, pyridazinyl or pyrazinyl group and R
2
represents hydrogen or a C
1-6
alkyl, alkenyl, alkynyl, phenyl, benzyl, pyridylmethyl, thienylmethyl, thiazolylmethyl group which may be optionally substituted with one or more allyl, alkoxy, alkoxycarbonyl, cyano, optionally substituted alkane sulphonyl groups or halogen atoms; and acid addition salts thereof.
One particularly preferred group of compounds are those wherein R
1
represents an optionally halogen substituted phenyl or pyridyl group and R
2
represents a alkyl group containing up to 4 carbon atoms which may optionally be substituted with one or more halogen atoms.
An especially preferred group of compounds are those wherein R
1
represents a 5-halopyrid-3-yl group and R
2
represents hydrogen or a haloalkyl, haloalkenyl or halobenzyl group.
Specific compounds of formula I according to the invention include those set out in Table I below in which the groups represented by R
1
and R
2
are given for each compound, together with the melting point (° C.) or an indication of the physical state of the compound.
TABLE I
Com-
pound
No
R
1
R
2
Melting Point
1
3,5-dichlorophenyl
methyl
145-146°
C.
2
3,5-difluorophenyl
methyl
93-94°
C.
3
2,3-difluorophenyl
methyl
oil
4
pentafluorophenyl
methyl
oil
5
2,3-dichlorophenyl
methyl
solid
6
4-methoxyphenyl
benzyl (Isomer A)
178.4°
C.
7
4-methoxyphenyl
benzyl (Isomer B)
95-100°
C.
8
phenyl
benzyl
90-90.5°
C.
9
3,5-difluorophenyl
H
112.1°
C.
10
3,5-difluorophenyl
benzyl
85.2°
C.
11
3,5-difluorophenyl
5,6-dichloropyrid-
143.2-144.2°
C.
3-ylmethyl
12
3,5-difluorophenyl
pyrid-2-ylmethyl
127.9-128.5°
C.
13
3,5-difluorophenyl
3-methylbenzyl
95.9-96.1°
C.
14
3,5-difluorophenyl
4-chlorobenzyl
95.5-96.7°
C.
15
3,5-difluorophenyl
pyrid-3-ylmethyl
78.2°
C.
16
3,5-difluorophenyl
3,5-methylenedi-
oil
oxybenzyl
17
3,5-difluorophenyl
3,5-
154.1°
C.
dichlorobenzyl
18
3,5-difluorophenyl
3,3-difluoroprop-
94.6°
C.
2-en-1-yl
19
3,5-difluorophenyl
2-hydroxy-2-
120.8°
C.
phenylethyl
20
3,5-difluorophenyl
1-phenyl-2-
168.8°
C.
hydroxyethyl
21
3,5-difluorophenyl
allyl
70.5°
C.
22
3,5-difluorophenyl
propargyl
108.4°
C.
23
3,5-difluorophenyl
2-fluoroethyl
oil
24
3,5-difluorophenyl
2-hydroxyethyl
100.4°
C.
25
3,5-difluorophenyl
2-methoxyethyl
54.8°
C.
26
3,5-difluorophenyl
2-cyanoethyl
115°
C.
27
3,5-difluorophenyl
5-chlorothien-2-
114°
C.
ylmethyl
28
3,5-difluorophenyl
6-chloropyrid-2-
gum
yl
29
3,5-difluorophenyl
2-methylthiazol-
140°
C.
5-ylmethyl
30
3,5-difluorophenyl
2-iminyl-2-
109°
C.
methoxyethyl
31
phenyl
benzyl
115-116°
C.
(exo-isomer)
32
phenyl
benzyl
97°
C.
(endo-isomer)
33
pyrid-3-yl
methyl
87°
C.
34
pyrid-3-yl
2-fluoroethyl
86-88°
C.
35
pyrid-3-yl
allyl
90-92°
C.
36
pyrid-3-yl
H
80-81°
C.
37
pyrid-3-yl
benzyl
119-120°
C.
38
pyrid-3-yl
ethyl
oil
39
pyrid-3-yl
t
-butoxycarbonyl-
gum
methyl
40
N-methylpyridinium-
t
-butoxycarbonyl
185-187°
C.
3-yl
(iodide)
41
6-chloropyridazin-3-yl
methyl
119-120 ac
42
pyrid-3-yl
propyl
oil
43
6-chloropyrazin-2-yl
methyl
80°
C.
44
pyrid-3-yl
methane-
163-164°
C.
sulphonyl-
methylsulphonyl
45
pyrid-3-yl
methane-
135°
C.
sulphonyl
46
6-chloropyrid-3-yl
methyl
gum
47
pyrid-3-yl
methoxymethyl
oil
48
pyrid-3-yl
ethoxymethyl
oil
49
pyrid-3-yl
cyanomethyl
90-91°
C.
50
pyrid-3-yl
ethoxycar-
gum
bonylmethyl
51
pyrid-3-yl
methoxycar-
gum
bonylmethyl
52
2-fluoro-4-nitrophenyl
methyl
100-102°
C.
53
3-fluorophenyl
methyl
oil
54
pyrid-3-yl
2-hydroxyethyl
155.2-156.8°
C.
55
5,6-dichloropyrid-3-yl
methyl
110.1-111.4°
C.
56
pyrid-3-yl
propargyl
119.8-121.1°
C.
57
pyrid-3-yl
methyl
gum
58
pyrid-3-yl
but-2-en-1-yl
193-194°
C.
59
3,5-difluorophenyl
4-nitrophenyl
96.9-97.9°
C.
60
5-chloropyrid-3-yl
methyl
152.8-154.5°
C.
61
pyrid-3-yl
phenyl
136-137°
C.
62
pyrazin-2-yl
methyl
76-76.9°
C.
63
2,6-dichloropyrimid-
methyl
95.3-96.8°
C.
4-yl
64
5-chloropyrid-3-yl
2-fluoroethyl
125.9-126.9°
C.
65
2,6-dichloropyrid-4-yl
methyl
165-165.8°
C.
66
2-chloro-6-
methyl
72-73°
C.
hydrazinopyrid-4-yl
67
pyrid-4-yl
methyl
74.5-76.1°
C.
68
5-bromopyrid-3-yl
methyl
144.1-145.2°
C.
69
5-chloropyrid-3-yl
vinyloxycarbonyl
gum
70
5-chloropyrid-3-yl
H
85-87°
C.
71
6-chloropyrid-2-yl
methyl
103.9-104.8°
C.
72
5-chloropyrid-3-yl
2,2,2-
109.5-111.5°
C.
trifluoroethyl
73
3,5-difluorophenyl
pyrid-2-yl
oil
74
5-chloropyrid-3-yl
phenyl
122-123°
C.
75
5-cloropyrid-3-yl
propargyl
110-112°
C.
76
5-cloropyrid-3-yl
allyl
78-80°
C.
77
5-methoxypyrid-3-yl
methyl
112.2-113.1°
C.
78
5-chloropyrid-3-yl
ethyl
116-118°
C.
79
5-chloropyrid-3-yl
butyl
48-50°
C.
80
5-methoxypyrid-3-yl
methyl
567.2-57°
C.
81
5-chloropyrid-3-yl
hexyl
resin
82
5-chloropyrid-3-yl
phenoxycarbonyl
117-123°
C.
83
5-chloropyrid-3-yl
2,2,2-trichloro-
oil
ethoxycarbonyl
84
5-chloropyrid-3-yl
ethoxycarbonyl
oil
85
5-chloropyrid-3-yl
fluoren-9-yl-
68-70°
C.
methyloxy-
carbonyl
86
5-chloropyrid-3-yl
ethoxycar-
gum
bonylmethyl
87
5-chloropyrid-3-yl
isopropyl
oil
88
5-chloropyrid-3-yl
4,4,4-trifluorobut-
143.9-145.1°
C.
3-on-1-en-1-yl
89
5-chloropyrid-3-yl
1-methyl-2,2,2-
152-155°
C.
trichloro-
ethoxycarbonyl
90
5-chloropyrid-3-yl
allyloxycbrbonyl
oil
91
5-chloropyrid-3-yl
benzyl-
oil
oxycarbonyl
92
5-chloropyrid-3-yl
2-chloro-
gum
ethoxycarbonyl
93
5-chloropyrid-3-yl
pentafluorobenzyl
143-144°
C.
94
5-chloropyrid-3-yl
4-nitrophenyl
213-214.5°
C.
95
5-chloropyrid-3-yl
acetyl
162-165°
C.
96
5-chloropyrid-3-yl
trifluoroacetyl
121-124°
C.
97
5-chloropyrid-3-yl
4-chlorobenzoyl
175-177°
C.
98
5-chloropyrid-3-yl
4-fluorobenzoyl
200-204°
C.
99
5-chloropyrid-3-yl
3-fluoropropyl
oil
100
5-chloropyrid-3-yl
2,4-bis(trifluoro-
112-114°
C.
methyl)benzyl
101
5-chloropyrid-3-yl
4-carboxybenzyl
gum
102
5-(prop-1-enyloxy)
methyl
gum
pyrid-3-yl
103
5-chloropyrid-3-yl
2,3-
102-103°
C.
difluorobenzyl
104
5-chloropyrid-3-yl
2-phenylethyl
oil
105
5-chloropyrid-3-yl
4-cyanophenyl
201-204°
C.
106
5-chloropyrid-3-yl
3,3-difluoropro-
oil
2-en-1-yl
107
5-chloropyrid-3-yl
carboxymethyl
165-167°
C.
108
5-chloropyrid-3-yl
3,5-
194-196°
C.
dibromobenzyl
109
5-chloropyrid-3-yl
3-chloro-4-
95-97
C.
fluorobenzyl
110
5-chloropyrid-3-yl
formyl
141-142°
C.
111
5-chloropyrid-3-yl
isopro-
gum
poxycarbonyl
112
5-chloropyrid-3-yl
benzenesulfonyl
210-211°
C.
113
5-chloropyrid-3-yl
2,4,6-
106-107°
C.
trifluorobenzyl
114
5-chloropyrid-3-yl
2,3,6-
125-127°
C.
trifluorobenzyl
115
5-chloropyrid-3-yl
1-cyano-1-
141-142°
C.
phenylmethyl
116
5-chloropyrid-3-yl
methoxycarbonyl
oil
117
5-chloropyrid-3-yl
pyr

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