Dihalopropene compounds insecticides containing them as...

Details Dihalopropene compounds insecticides containing them as... Dihalopropene compounds insecticides containing them as...

1999-06-02

2001-04-10

Padmanabhan, Sreeni (Department: 1621)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

C514S277000, C546S313000, C546S314000, C546S315000, C546S323000

Reexamination Certificate

active

06214835

ABSTRACT:

TECHNICAL FIELD
The present invention relates to dihalopropene compounds, insecticides containing them as active ingredients, and intermediates for their production.
BACKGROUND ART
As disclosed in JP-A 48-86835/1973 and JP-A 49-1526/1974, for example, it is well known that some kinds of propene compounds can be used as active ingredients of insecticides.
In view of their insecticidal activity, however, it cannot always be said that these compounds are satisfactorily effective for the control of noxious insects.
DISCLOSURE OF INVENTION
The present inventors have intensively studied to find a compound having excellent insecticidal activity. As a result, they have found that particular dihalopropene compounds have satisfactory insecticidal activity for the control of noxious insects, thereby completing the present invention.
That is, the present invention provides dihalopropene compounds of the general formula:
wherein m is an integer of 0 to 4;
n is an integer of 0 to 2;
X's are independently chlorine or bromine;
Y is oxygen, NH or sulfur; and
Z is oxygen, sulfur or NR
15
in which R
15
is hydrogen or C
1
-C
3
alkyl;
R
2
, R
3
and R
4
are independently halogen, C
1
-C
3
haloalkyl or C
1
-C
3
alkyl;
R
5
, R
6
and R
7
are independently hydrogen, C
1
-C
3
alkyl or trifluoromethyl;
L is C═W, C(═W)NR
13
, NR
13
C(═W), SO
2
NR
13
, NR
13
SO
2
, NR
13
C(═W
1
)—W, WC(═W
1
)NR
13
or NR
14
C(═W)NR
13
in which W and W
1
are independently oxygen or sulfur, and R
13
and R
14
are independently hydrogen, C
1
-C
10
alkyl, C
1
-C
5
haloalkyl, C
2
-C
10
alkenyl, C
2
-C
6
haloalkenyl, C
3
-C
9
alkynyl or C
3
-C
5
haloalkynyl;
R
1
is C
1
-C
10
alkyl, C
1
-C
5
haloalkyl, C
2
-C
10
alkenyl, C
2
-C
6
haloalkenyl, C
3
-C
9
alkynyl, C
3
-C
5
haloalkynyl, C
2
-C
7
alkoxyalkyl, C
2
-C
7
alkylthioalkyl,
C
3
-C
6
cycloalkyl optionally substituted with C
1
-C
4
alkyl, C
1
-C
4
alkoxy or C
1
-C
3
haloalkoxy,
C
4
-C
9
cycloalkylalkyl optionally substituted with C
1
-C
4
alkyl,
C
5
-C
6
cycloalkenyl optionally substituted with C
1
-C
4
alkyl,
C
6
-C
8
cycloalkenylalkyl optionally substituted with C
1
-C
4
alkyl, an optionally substituted heterocyclic group, Q
1
, Q
2
, Q
3
or Q
4
of the general formula:
in which M is oxygen, NH or sulfur,
l is an integer of 0 to 5,
p is an integer of 0 to 5, and
q is an integer of 1 to 5;
R
12
is halogen, cyano, nitro, pentafluorosulfanyl (F
5
S), C
1
-C
8
alkyl, C
1
-C
3
haloalkyl, C
1
-C
7
alkoxy, C
1
-C
3
haloalkoxy, C
1
-C
3
alkylthio, C
1
-C
3
haloalkylthio, C
3
-C
6
alkenyloxy, C
3
-C
6
haloalkenyloxy, C
1
-C
3
hydroxyalkyl, C
2
-C
4
alkenyl, C
2
-C
4
haloalkenyl, C
2
-C
4
alkynyl, C
2
-C
4
alkynyloxy, C
2
-C
4
haloalkynyl, C
2
-C
4
haloalkynyloxy, C
2
-C
4
alkoxyalkyl, C
2
-C
4
alkylthioalkyl, C
3
-C
6
cycloalkyl, C
5
-C
6
cycloalkenyl, C
2
-C
5
alkoxycarbonyl, C
3
-C
6
cycloalkyloxy, C
5
-C
6
cycloalkenyloxy,
phenyl optionally substituted with halogen, C
1
-C
4
alkyl, C
1
-C
3
haloalkyl, C
1
-C
3
alkoxy or C
1
-C
3
haloalkoxy,
phenoxy optionally substituted with halogen, C
1
-C
4
alkyl, C
1
-C
3
haloalkyl, C
1
-C
3
alkoxy or C
1
-C
3
haloalkoxy,
benzyl optionally substituted with halogen, C
1
-C
4
alkyl, C
1
-C
3
haloalkyl, C
1
-C
3
alkoxy or C
1
-C
3
haloalkoxy,
benzyloxy optionally substituted with halogen, C
1
-C
4
alkyl, C
1
-C
3
haloalkyl, C
1
-C
3
alkoxy or C
1
-C
3
haloalkoxy;
or when l is an integer of 2 to 5, adjacent two R
12
are combined together at their ends to form trimethylene or tetramethylene, methylenedioxy optionally substituted with halogen or C
1
-C
3
alkyl, or ethylenedioxy optionally substituted with halogen or C
1
-C
3
alkyl; and
R
8
, R
9
, R
10
and R
11
are independently hydrogen, C
1
-C
3
alkyl or trifluoromethyl.
The present invention further provides compounds of the general formula:
which are useful as intermediates for the production of some of the present compounds, wherein X's are independently chlorine or bromine; R
18
and R
19
are independently halogen or C
1
-C
3
alkyl; R
17
is amino or carboxyl; R
5
, R
6
and R
7
are independently hydrogen, C
1
-C
3
alkyl or trifluoromethyl; and m is an integer of 0 to 4. More particularly, the present invention provides phenol compounds of the general formula:
wherein R
20
is Q
1
as defined above, or 2-pyridyl, 2-pyrazinyl, 2-indolyl, 2-pyrrolyl, 2-quinolyl, 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, 3-pyridyl or 4-pyridyl, each of which may be optionally substituted with (R
16
)
s
in which R
16
is halogen, nitro, cyano, C
1
-C
4
alkyl, C
1
-C
3
haloalkyl, C
1
-C
4
alkoxy, C
1
-C
3
haloalkoxy, C
1
-C
3
alkylthio, C
1
-C
3
haloalkylthio, C
1
-C
2
alkylsulfinyl, C
1
-C
2
alkylsulfonyl, C
1
-C
2
haloalkylsulfinyl, C
1
-C
2
haloalkylsulfonyl, C
2
-C
4
alkenyl, C
2
-C
4
haloalkenyl, C
2
-C
4
alkynyl, C
2
-C
4
haloalkynyl, amino, dimethylamino, acetamido, acetyl, haloacetyl, formyl, carboxyl, methoxycarbonyl, C
3
-C
6
cycloalkyl, (C
1
-C
2
alkyl)aminocarbonyl, [di(C
1
-C
2
alkyl)amino]-carbonyl,
phenyl optionally substituted with halogen, C
1
-C
4
alkyl, C
1
-C
3
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
3
haloalkoxy,
benzyl optionally substituted with halogen, C
1
-C
4
alkyl, C
1
-C
3
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
3
haloalkoxy,
phenoxy optionally substituted with halogen, C
1
-C
4
alkyl, C
1
-C
3
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
3
haloalkoxy,
benzyloxy optionally substituted with halogen, C
1
-C
4
alkyl, C
1
-C
3
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
3
haloalkoxy,
or pyridyloxy optionally substituted with halogen, C
1
-C
4
alkyl, C
1
-C
3
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
3
haloalkoxy; and
s is an integer of 0 to 7;
R
2
and R
3
are independently halogen, C
1
-C
3
haloalkyl or C
1
-C
3
alkyl;
R
5
, R
6
and R
7
are independently hydrogen, C
1
-C
3
alkyl or trifluoromethyl;
L
1
is C═W, C(═W)NR
131
or SO
2
NR
131
in which W is oxygen or sulfur, and R
131
is hydrogen or C
1
-C
3
alkyl.
As more specific examples of these phenol compounds, the present invention provides phenol compounds wherein R
20
is Q
1
in which p=0 or R
1
as defined above in which the 5- or 6-membered heterocyclic group is 2-pyridyl, 2-pyrazinyl, 2-indolyl, 2-pyrrolyl, 2-quinolyl, 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, 3-pyridyl or 4-pyridyl; and
phenol compounds wherein R
20
is Q
1
in which p=0 or R
1
as defined above in which the 5- or 6-membered heterocyclic group is 2-pyridyl, 2-pyrazinyl, 2-indolyl, 2-pyrrolyl, 2-quinolyl, 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, 3-pyridyl or 4-pyridyl, and L
1
is C(═W)NR
131
or SO
2
NR
131
; and
phenol compounds, wherein R
20
is Q
1
in which p=0 or R
1
as defined above in which the 5- or 6-membered heterocyclic group is 2-pyridyl, 2-pyrazinyl, 2-indolyl, 2-pyrrolyl, 2-quinolyl, 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, 3-pyridyl or 4-pyridyl; R
2
and R
3
are halogen or C
1
-C
3
alkyl; and L
1
is C(═W)NR
131
or SO
2
NR
131
; and the following compounds:
3,5-dichloro-4-(3-(N-(4-trifluoromethylphenyl)carbamoyl)propyloxy)phenol;
3,5-dichloro-4-(4-(N-(4-trifluoromethylphenyl)carbamoyl)butyloxy)phenol;
3,5-dichloro-4-(3-(N-(5-trifluoromethyl-2-pyridyl)carbamoyl)propyloxy)-phenol; and
3,5-dichloro-4-(4-(N-(5-trifluoromethyl-2-pyridyl)carbamoyl)butyloxy)-phenol.
DETAILED DESCRIPTION OF THE INVENTION
The variables in the above formulas for the present compounds and their intermediates can take the following specific examples.
Examples of the substituent on the optionally substituted heterocyclic group represented by R
1
are those of the formula: (Ri
6
)
s
in which R
16
is halogen, nitro, cyano, C
1
-C
4
alkyl, C
1
-C
3
haloalkyl, C
1
-C
4
alkoxy, C
1
-C
3
haloalkoxy, C
1
-C
3
alkylthio, C
1
-C
3
haloalkylthio, C
1
-C
2
alkylsulfinyl, C
1
-C
2
alkylsulfonyl, C
1
-C
2
haloalkylsulfinyl, C
1
-C
2
haloalkylsulfonyl, C
2
-C
4
alkenyl, C
2
-C
4
haloalkenyl, C
2
-C
4
alkynyl, C
2
-C
4
haloalkynyl, amino, dimethylamino, acetamido, acetyl, haloac

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