Oxime compounds, their use, and intermediates for their...

Details Oxime compounds, their use, and intermediates for their... Oxime compounds, their use, and intermediates for their...

1999-10-01

2002-08-20

Vollano, Jean F. (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

C564S256000

Reexamination Certificate

active

06437184

ABSTRACT:

TECHNICAL FIELD
The present invention relates to oxime compounds, their use, and intermediates for their production.
BACKGROUND ART
As disclosed, for example, in JP-A61-72733 and JP-A61-260054, it is well known that certain types of oxime compounds can be used as the active ingredients of insecticides. These compounds are, however, not necessarily satisfactory for the active ingredients of insecticidal/acaricidal agents in view of their insecticidal activity.
DISCLOSURE OF INVENTION
Under these circumstances, the present inventors have extensively studied to find out compounds with excellent insecticidal/acaricidal activity. As a result, they have found that oxime compounds of formula (1) as depicted below have excellent insecticidal/acaricidal activity, thereby completing the present invention.
Thus, the present invention provides oxime compounds of formula (1)
(hereinafter referred to as the present compound(s))
wherein:
R
1
, R
2
, and R
3
are independently halogen, C
1
-C
3
alkyl, C
1
-C
3
haloalkyl, C
1
-C
3
alkoxy, C
1
-C
3
haloalkoxy, nitro, or cyano;
R
4
is 3,3-dihalogeno-2-propenyl;
a is an integer of 0 to 2;
Y is oxygen, sulfur, or NH;
Z is oxygen, sulfur, or NR
5
wherein R
5
is hydrogen, acetyl, or C
1
-C
3
alkyl;
X is X
1
or X
2
of formula (2)
 wherein:
R
6
is hydrogen, C
1
-C
8
alkyl, C
2
-C
6
haloalkyl, C
3
-C
6
alkenyl, C
3
-C
6
haloalkenyl, C
3
-C
6
alkynyl, C
3
-C
6
haloalkynyl, or triphenylmethyl,
or C
3
-C
7
cycloalkyl optionally substituted with C
1
-C
4
alkyl,
or C
4
-C
10
cycloalkylalkyl optionally substituted with C
1
-C
4
alkyl on the ring thereof,
or C
5
-C
6
cycloalkenyl optionally substituted with C
1
-C
4
alkyl,
or C
6
-C
8
cycloalkenylalkyl optionally substituted with C
1
-C
4
alkyl on the ring thereof,
or C
1
-C
6
alkyl substituted with cyano, nitro, (C
1
-C
4
alkoxy)-carbonyl, C
1
-C
4
alkylthio, or C
1
-C
4
alkoxy,
or T
1
-1, T
1
-2, T
1
-3, T
1
-4, T
1
-5, T
1
-6, or T
1
-7 of formula (3)
 wherein:
(R
10
)
b
's are zero to five identical or different substituents selected from halogen, C
1
-C
6
alkyl, C
1
-C
3
haloalkyl, C
2
-C
6
alkenyl, C
2
-C
6
haloalkenyl, C
2
-C
6
alkynyl, C
2
-C
6
haloalkynyl, C
1
-C
6
alkoxy, C
1
-C
3
haloalkoxy, C
3
-C
6
alkenyloxy, C
3
-C
6
haloalkenyloxy, C
3
-C
6
alkynyloxy, C
3
-C
6
haloalkynyloxy, (C
1
-C
5
alkoxy)carbonyl, cyano, or nitro;
R
11
, R
12
, R
13
, and R
14
are independently hydrogen, C
1
-C
3
alkyl, or trifluoromethyl;
D is —CH═ or nitrogen;
J is oxygen or sulfur;
b is an integer of 0 to 5;
d is an integer of 1 to 3;
e is an integer of 0 to 3;
f is an integer of 2 to 4;
R
15
is C
1
-C
6
alkyl, C
1
-C
3
haloalkyl, C
2
-C
6
alkenyl, or C
3
-C
6
cycloalkyl,
or 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; and
R
16
and R
42
are independently C
1
-C
6
alkyl, C
2
-C
6
haloalkyl, C
3
-C
6
alkenyl, C
3
-C
6
haloalkenyl, C
3
-C
6
alkynyl, C
3
-C
6
haloalkynyl, or C
3
-C
6
cycloalkyl,
or 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,
or 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 on the ring thereof;
R
7
is hydrogen, C
1
-C
6
alkyl, C
1
-C
3
haloalkyl, C
3
-C
6
cycloalkyl, cyano, cyano C
1
-C
3
alkyl, (C
1
-C
4
alkoxy)carbonyl, or (C
1
-C
4
alkoxy)-carbonyl(C
1
-C
3
)alkyl,
or 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,
or 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 on the ring thereof;
R
8
and R
9
are independently hydrogen, C
1
-C
11
alkyl, C
1
-C
6
haloalkyl, C
2
-C
6
alkenyl, C
2
-C
6
haloalkenyl, C
2
-C
6
alkynyl, C
2
-C
6
haloalkynyl, C
2
-C
10
alkoxyalkyl, C
2
-C
10
alkylthioalkyl, or naphthyl,
or C
3
-C
7
cycloalkyl optionally substituted with C
1
-C
4
alkyl,
or C
4
-C
10
cycloalkylalkyl optionally substituted with C
1
-C
4
alkyl on the ring thereof,
or C
5
-C
6
cycloalkenyl optionally substituted with C
1
-C
4
alkyl,
or C
6
-C
8
cycloalkenylalkyl optionally substituted with C
1
-C
4
on the ring thereof,
or T
2
-1 or T
2
-2 of formula (4)
 wherein:
(R
7
)
b
's are zero to five identical or different substituents selected from halogen, C
1
-C
6
alkyl, C
1
-C
3
haloalkyl, C
2
-C
6
alkenyl, C
2
-C
6
haloalkenyl, C
2
-C
6
alkynyl, C
2
-C
6
haloalkynyl, C
1
-C
6
alkoxy, C
1
-C
3
haloalkoxy, C
3
-C
6
alkenyloxy, C
3
-C
6
haloalkenyloxy, C
3
-C
6
alkynyloxy, C
3
-C
6
haloalkynyloxy, 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
1
-C
3
hydroxyalkyl, C
2
-C
4
alkoxyalkyl, C
2
-C
4
alkylthioalkyl, dimethylamino, acetamido, acetyl, formyl, carboxyl, (C
1
-C
2
alkyl)aminocarbonyl, [di(C
1
-C
2
alkyl)amino]carbonyl, (C
1
-C
6
alkoxy)carbonyl, C
3
-C
6
cycloalkyl, C
5
-C
6
cycloalkenyl, C
3
-C
6
cycloalkyloxy, C
5
-C
6
cycloalkenyloxy, pentafluorosulfanyl (F
5
S), cyano, or nitro,
or 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,
or 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,
or 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 on the ring thereof,
or 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 on the ring thereof,
or when b is 2 to 5, two adjacent R
17
's are combined together at their ends to form trimethylene or tetramethylene,
or when b is 2 to 5, two adjacent R
17
's are combined together at their ends to form methylenedioxy optionally substituted with halogen or C
1
-C
3
alkyl,
or when b is 2 to 5, two adjacent R
17
's are combined together at their ends to form ethylenedioxy optionally substituted with halogen or C
1
-C
3
alkyl;
D is —CH═ or nitrogen;
R
11
and R
12
are independently hydrogen, C
1
-C
3
alkyl, or trifluoromethyl;
b is an integer of 0 to 5; and
d is an integer of 1 to 3;
or a heterocyclic group, exclusive of pyridine ring, which heterocyclic group may be optionally substituted with one to three identical or different (R
18
)
g
's,
wherein:
R
18
is halogen, C
1
-C
6
alkyl, C
1
-C
3
haloalkyl, C
2
-C
6
alkenyl, C
2
-C
6
haloalkenyl, C
2
-C
6
alkynyl, C
2
-C
6
haloalkynyl, C
1
-C
6
alkoxy, C
1
-C
3
haloalkoxy, C
3
-C
6
alkenyloxy, C
3
-C
6
haloalkenyloxy, C
3
-C
6
alkynyloxy, C
3
-C
6
haloalkynyloxy, 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
1
-C
3
hydroxyalkyl, C
2
-C
4
alkoxyalkyl, C
2
-C
4
alkylthioalkyl, cyano, or nitro,
or 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; and
g is an integer of 1 to 3;
or R
8
and R
9
are combined together at their ends to form a saturated or unsaturated 5- or 6-membered ring containing zero to two oxygen or sulfur atoms in the ring;
A
1
is A
1
-1, A
1
-2, A
1
-3, A
1
-4, A
1
-5, A
1
-6, A
1
-7, A
1
-8, A
1
-9, A
1
-10, A
1
-11, or A
1
-12 of formula (5)
A
1
-1: —(CR
19
═CR
20
)
h
—(CR
21
R
22
)
i
—
A
1
-2: —(CR
19
═CR
20
)
h
—(CR
21
R
22
)
j
—Q
1
—(CR
23
R
24
)
k
—
A
1
-3: —(CR
19
═CR
20
)
h
—(CR
21
R
22
)
j
—Q
1
—(CR
23
R
24
)
m
—CR
25
═CR
26
—(CR
27
R
28
)
n
—
A
1
-4: —(CR
19
═CR
20
)
h
—(CR
21
R
22
)
j
—Q
1
—(CR
23
R
24
)
m
—C≡C—(CR
25
R
26
)
n
—
A
1
-5: —(CR
19
═CR
20
)
h
—(CR
21
R
22
)
j
—Q
1
—(CR
23
R
24
)
p
—E—(CR
25
R
26
)
q
—
A
1
-6: —(CR
19
═CR
20
)
h
—(CR
21
R
22
)
j
—Q
1
—(CR
23
R
24
)
r
—Q
2
—(CR
25
R
26
)
s
—
A
1
-7: —U

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