Condensed heterocylic compounds and herbicides containing them

Details Condensed heterocylic compounds and herbicides containing them Condensed heterocylic compounds and herbicides containing them

2001-02-07

2003-07-01

McKane, Joseph K. (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C544S238000

Reexamination Certificate

active

06586368

ABSTRACT:

TECHNICAL FIELD
The present invention relates to condensed heterocyclic compounds and their use.
DISCLOSURE OF THE INVENTION
The present inventors have extensively studied to find compounds having excellent herbicidal activity. As a result, they have found that the condensed heterocyclic compounds of general formula I as depicted below have excellent herbicidal activity, thereby completing the present invention.
The present invention provides condensed heterocyclic compounds of general formula I:
(hereinafter referred to as the present compounds)
wherein T is carbon or nitrogen; when T is carbon, then the bond between T and A is a double bond, the bond between A and Y is a single bond, and Y is oxygen, sulfur, or N—R
142
; or when T is nitrogen, then the bond between T and A is a single bond, the bond between A and Y is a double bond, and Y is nitrogen or C—R
152
;
wherein R
142
is hydrogen, C
1
-C
5
alkyl, C
1
-C
5
haloalkyl, C
3
-C
6
alkenyl, C
3
-C
6
alkynyl, cyano, —COR
143
, —N(R
145
)R
146
, or —N═C(R
147
)R
148
; R
152
is hydrogen, halogen, C
1
-C
3
alkyl, nitro, amino, cyano, or —COR
153
;
 wherein R
143
is hydrogen, C
1
-C
3
alkyl, C
1
-C
3
haloalkyl, hydroxyl, C
1
-C
5
alkoxy, or —N(R
156
)N
157
; R
145
and R
146
are independently hydrogen, C
1
-C
5
alkyl, C
1
-C
5
haloalkyl, formyl, (C
1
-C
5
alkyl)carbonyl, (C
1
-C
5
haloalkyl)carbonyl, or (C
1
-C
6
alkoxy)carbonyl; R
147
and R
148
are independently hydrogen or C
1
-C
5
alkyl; R
153
is hydrogen, C
1
-C
3
alkyl, C
1
-C
3
haloalkyl, hydroxyl, C
1
-C
5
alkoxy, or —N(R
154
)R
155
;
wherein R
156
and R
157
are independently hydrogen, C
1
-C
5
alkyl, C
1
-C
5
haloalkyl, formyl, (C
1
-C
5
alkyl)carbonyl, (C
1
-C
5
haloalkyl)carbonyl, or (C
1
-C
5
alkoxy)carbonyl; R
154
and R
155
are independently hydrogen, C
1
-C
5
alkyl, C
1
-C
5
haloalkyl, (C
1
-C
5
alkoxy)carbonyl, formyl, (C
1
-C
5
alkyl)carbonyl, or (C
1
-C
5
haloalkyl)carbonyl;
A is nitrogen or C—R
141
wherein R
141
is hydrogen, halogen, or C
1
-C
3
alkyl;
R
1
is hydrogen, halogen, C
1
-C
3
alkyl, C
1
-C
3
haloalkyl, hydroxymethyl, nitro, or cyano;
R
2
is hydrogen, halogen, C
1
-C
11
alkyl, C
1
-C
11
haloalkyl, hydroxymethyl, nitro, cyano, —N(R
9
)R
10
, —OR
11
, —SR
12
, —SO
2
R
13
, —COX, —COOR
14
, —CON(R
15
)R
16
, —COR
17
, —C(R
26
)═NOR
19
, —C(R
27
)═C(R
21
)R
22
, or —CH(R
23
)—CH(R
24
)R
25
;
R
3
is hydrogen, halogen, C
1
-C
11
alkyl, C
1
-C
11
haloalkyl, hydroxymethyl, nitro, cyano, —N(R
59
)R
60
, —OR
61
, —SR
62
, —SO
2
R
63
, —COX, —COOR
64
, —CON(R
65
)R
66
, —COR
67
, —C(R
76
)═NOR
69
, —C(R
77
)═C(R
71
)R
72
, or —CH(R
73
)—CH(R
74
)R
75
;
R
4
is hydrogen, halogen, C
1
-C
3
alkyl, C
1
-C
3
haloalkyl, hydroxymethyl, nitro, or cyano;
 wherein X is chlorine or bromine;
R
9
and R
59
are independently hydrogen, C
1
-C
5
alkyl, (C
1
-C
5
alkyl)carbonyl, or (C
1
-C
5
alkoxy)carbonyl;
R
10
, R
11
, and R
12
are independently hydrogen, C
1
-C
10
alkyl, C
1
-C
10
haloalkyl, C
3
-C
10
cycloalkyl, C
3
-C
10
halocycloalkyl, C
3
-C
10
cycloalkyl C
1
-C
3
alkyl, C
3
-C
10
alkenyl, C
3
-C
10
haloalkenyl, C
3
-C
10
alkynyl, C
3
-C
10
haloalkynyl, cyano C
1
-C
6
alkyl, (C
1
-C
5
alkyl)carbonyl, (C
1
-C
5
haloalkyl)carbonyl, (C
3
-C
10
cycloalkyl)carbonyl, (C
1
-C
5
alkyl)carbonyl, C
1
-C
5
alkyl, (C
1
-C
5
haloalkyl)carbonyl C
1
-C
5
alkyl, hydroxy C
1
-C
5
alkyl, C
1
-C
5
alkoxy C
1
-C
5
alkyl, C
1
-C
5
alkylthio C
1
-C
5
alkyl, (C
1
-C
5
alkoxy)carbonyl, carboxy C
1
-C
5
alkyl, (C
1
-C
10
alkoxy)carbonyl C
1
-C
5
alkyl, (C
1
-C
10
haloalkoxy)carbonyl C
1
-C
5
alkyl, (C
3
-C
10
cycloalkoxy)carbonyl C
1
-C
5
alkyl, (C
3
-C
10
halocycloalkoxy)carbonyl C
1
-C
5
alkyl, —C(R
43
)(R
44
)—C(═O)ON(R
45
)R
46
, —C(R
47
)(R
48
) —CON(R
49
)R
50
, —CH
2
—C(R
56
)═NOR
55
, —CHMe—C(R
58
)═NOR
57
, (C
3
-C
10
alkenoxy)carbonyl C
1
-C
5
alkyl, (C
3
-C
10
alkynoxy)carbonyl C
1
-C
5
alkyl, phenoxycarbonyl, benzyloxycarbonyl, carboxy (C
1
-C
5
alkoxy)carbonyl C
1
-C
5
alkyl, (C
1
-C
10
alkoxy)carbonyl (C
1
-C
5
alkoxy)carbonyl C
1
-C
5
alkyl, (C
1
-C
10
haloalkoxy)carbonyl(C
1
-C
5
alkoxy)carbonyl C
1
-C
5
alkyl, (C
3
-C
10
cycloalkoxy)carbonyl(C
1
-C
5
alkoxy)carbonyl C
1
-C
5
alkyl, (C
3
-C
10
alkenoxy)carbonyl(C
1
-C
5
alkoxy)carbonyl C
1
-C
5
alkyl, (C
3
-C
10
alkynoxy)carbonyl(C
1
-C
5
alkoxy)carbonyl C
1
-C
5
alkyl, carboxy(C
1
-C
5
alkyl)carbonyl, (C
1
-C
10
alkoxy)carbonyl(C
1
-C
5
alkyl)carbonyl, (C
1
-C
10
haloalkoxy)carbonyl(C
1
-C
5
alkyl)carbonyl, C
1
-C
5
alkylsulfonyl, C
1
-C
5
haloalkylsulfonyl, —SO
2
N(R
51
)R
52
, —CON(R
53
)R
54
, optionally substituted benzyl, or optionally substituted phenyl;
R
60
, R
61
, and R
62
are independently hydrogen, C
1
-C
10
alkyl, C
1
-C
10
haloalkyl, C
3
-C
10
cycloalkyl, C
3
-C
10
halocycloalkyl, C
3
-C
10
cycloalkyl C
1
-C
3
alkyl, C
3
-C
10
alkenyl, C
3
-C
10
haloalkenyl, C
3
-C
10
alkynyl, C
3
-C
10
haloalkynyl, cyano C
1
-C
6
alkyl, (C
1
-C
5
alkyl)carbonyl, (C
1
-C
5
haloalkyl)carbonyl, (C
3
-C
10
cycloalkyl)carbonyl, (C
1
-C
5
alkyl)carbonyl C
1
-C
5
alkyl, (C
1
-C
5
haloalkyl)carbonyl C
1
-C
5
alkyl, hydroxy C
1
-C
5
alkyl, C
1
-C
5
alkoxy C
1
-C
5
alkyl, C
1
-C
5
alkylthio C
1
-C
5
alkyl, (C
1
-C
5
alkoxy)carbonyl, carboxy C
1
-C
5
alkyl, (C
1
-C
10
alkoxy)carbonyl C
1
-C
5
alkyl, (C
1
-C
10
haloalkoxy)carbonyl C
1
-C
10
alkyl, (C
3
-C
10
cycloalkoxy)carbonyl C
1
-C
5
alkyl, (C
3
-C
10
halocycloalkoxy)carbonyl C
1
-C
5
alkyl, —C(R
163
)(R
164
)—C(═O)ON(R
165
)R
166
, —C(R
167
)R
168
)—CON(R
169
)R
170
, —CH
2
—C(═NOR
175
)R
176
, —CHMe—C(═NOR
177
)R
178
, (C
3
-C
10
alkenoxy)carbonyl C
1
-C
5
alkyl, (C
3
-C
10
alkynoxy)carbonyl C
1
-C
5
alkyl, phenoxycarbonyl, benzyloxycarbonyl, carboxy(C
1
-C
5
alkoxy)carbonyl C
1
-C
5
alkyl, (C
1
-C
10
alkoxy)carbonyl (C
1
-C
5
alkoxy)carbonyl C
1
-C
5
alkyl, (C
1
-C
10
haloalkoxy)carbonyl (C
1
-C
5
alkoxy)carbonyl C
1
-C
5
alkyl, (C
3
-C
10
cycloalkoxy)carbonyl(C
1
-C
5
alkoxy)carbonyl C
1
-C
5
alkyl, (C
3
-C
10
alkenoxy)carbonyl(C
1
-C
5
alkoxy)carbonyl C
1
-C
5
alkyl, (C
3
-C
10
alkynoxy)carbonyl(C
1
-C
5
alkoxy)carbonyl C
1
-C
5
alkyl, carboxy(C
1
-C
5
alkyl)carbonyl, (C
1
-C
110
alkoxy)carbonyl(C
1
-C
5
alkyl)carbonyl, (C
1
-C
10
haloalkoxy)carbonyl(C
1
-C
5
alkyl)carbonyl, C
1
-C
5
alkylsulfonyl, C
1
-C
5
haloalkylsulfonyl, —SO
2
N(R
171
)R
172
, —CON(R
173
)R
174
, optionally substituted benzyl, or optionally substituted phenyl;
 wherein R
43
, R
44
, R
163
, and R
164
are independently hydrogen, halogen, C
1
-C
5
alkyl, or C
1
-C
5
haloalkyl;
R
45
, R
46
, R
165
, and R
166
are independently hydrogen, C
1
-C
5
alkyl, C
1
-C
5
haloalkyl, C
3
-C
8
cycloalkyl, C
3
-C
6
alkenyl, or C
3
-C
6
alkynyl; or R
45
and R
46
may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring, or R
165
and R
166
may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring;
R
47
, R
48
, R
167
, and R
168
are independently hydrogen, halogen, C
1
-C
5
alkyl, or C
1
-C
5
haloalkyl;
R
49
, R
50
, R
169
, and R
170
are independently hydrogen, C
1
-C
5
alkyl, C
1
-C
5
haloalkyl, C
3
-C
8
cycloalkyl, C
3
-C
6
alkenyl, or C
3
-C
6
alkynyl; or R
49
and R
50
may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring, or R
169
and R
170
may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring;
R
51
, R
52
, R
171
, and R
172
are independently hydrogen, C
1
-C
5
alkyl, C
1
-C
5
haloalkyl, C
3
-C
8
cycloalkyl, C
3
-C
6
alkenyl, or C
3
-C
6
alkynyl; or R
51
and R
52
may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring containing zero to on

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