Bicyclic amines

Details Bicyclic amines Bicyclic amines

2000-06-26

2002-05-21

Fan, Jane (Department: 1625)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

C514S256000, C514S247000, C544S238000, C544S333000, C544S405000

Reexamination Certificate

active

06391883

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 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) were 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 alkyl, 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-3-
143.2-144.2° C.
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
3,4-methylenedioxy-
oil
benzyl
 17
3,5-difluorophenyl
3,5-dichlorobenzyl
154.1° C.
 18
3,5-difluorophenyl
3,3-difluoroprop-2-en-
94.6° C.
1-yl
 19
3,5-difluorophenyl
2-hydroxy-2-phenyl-
120.8° C.
ethyl
 20
3,5-difluorophenyl
1-phenyl-2-hydroxy-
168.8° C.
ethyl
 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-yl-
114° C.
methyl
 28
3,5-difluorophenyl
6-chloropyrid-2-yl
gum
 29
3,5-difluorophenyl
2-methylthiazol-5-yl-
140° C.
methyl
 30
3,5-difluorophenyl
2-iminyl-2-methoxy-
109° C.
ethyl
 31
phenyl
benzyl (exo-isomer)
115-116° C.
 32
phenyl
benzyl (endo-isomer)
97° C.
 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
 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-methylpyridini-
t
-butoxycarbonyl
185-187° C.
um-3-yl
(iodide)
 41
6-chloropyridazin-
methyl
119-120° C.
3-yl
 42
pyrid-3-yl
propyl
oil
 43
6-chloropyrazin-2-yl
methyl
80° C.
 44
pyrid-3-yl
methane-
163-164° C.
sulphonylmethylsul-
phonyl
 45
pyrid-3-yl
methane-sulphonyl
135° C.
 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
ethoxycarbonylmethyl
gum
 51
pyrid-3-yl
methoxycarbonyl-
gum
methyl
 52
2-fluoro-4-nitro-
methyl
100-102° C.
phenyl
 53
3-fluorophenyl
methyl
oil
 54
pyrid-3-yl
2-hydroxyethyl
155.2-156.8° C.
 55
5,6-dichloropyrid-
methyl
110.1-111.4° C.
3-yl
 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-dichloropyri-
methyl
95.3-96.8° C.
mid-4-yl
 64
5-chloropyrid-3-yl
2-fluoroethyl
125.9-126.9° C.
 65
2,6-dichloropyrid-4-
methyl
165-165.8° C.
yl
 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-trifluoroethyl
109.5-111.5° C.
 73
3,5-difluorophenyl
pyrid-2-yl
oil
 74
5-chloropyrid-3-yl
phenyl
122-123° C.
 75
5-chloropyrid-3-yl
propargyl
110-112° C.
 76
5-chloropyrid-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-ethoxypyrid-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-ylmeth-
68-70° C.
yloxycarbonyl
 86
5-chloropyrid-3-yl
ethoxycarbonyl-
gum
methyl
 87
5-chloropyrid-3-yl
isopropyl
oil
 88
5-chloropyrid-3-yl
4,4,4-trifluorobut-3-
143.9-145.1° C.
on-1-en-1-yl
 89
5-chloropyrid-3-yl
1-methyl-2,2,2-
152-155° C.
trichloroethoxy-
carbonyl
 90
5-chloropyrid-3-yl
allyloxycarbonyl
oil
 91
5-chloropyrid-3-yl
benzyloxycarbonyl
oil
 92
5-chloropyrid-3-yl
2-chloroethoxycar-
gum
bonyl
 93
5-chloropyrid-3-yl
pentafluorobenzyl
143-144° C.
 94
5-chloropyrid-3-yl
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-eny

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