Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2000-11-30
2001-09-11
Lambkin, Deborah C. (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C546S269100, C548S131000, C514S364000
Reexamination Certificate
active
06288088
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a novel oxadiazoline derivative and agrochemical composition comprising it.
BACKGROUND ART
A large number of synthetic compounds having pest-controlling activities have so far been used as insecticides. Most of them, however, belong to the family of organic phosphoric acid esters, carbamic acid esters, organic chlorine-containing compounds or pyrethroid compounds.
On the other hand, it isreportedthat 1-arylpyrazole derivatives having a hydrogen or halogen atom or an alkyl, cycloalkyl, haloalkyl, cyano, nitro, carbamoyl or thiocarbamoyl group at position 3 of the pyrazole ring exhibit insecticidal activity [JP-A-228065/1987, 207259/1987, 148240/1993, 282366/1990, 86054/1993, and JP-A-500319/1995, etc.].
However, while these pyrazole derivatives are high in insecticidal activity, they show high toxicity to man, animals and fish. In some cases, they show toxicity even in natural enemies to pests. Moreover, these compounds tend to remain in soil to a considerable extent. For these and other reasons, satisfactory effects are not always obtained under the existing circumstances.
DISCLOSURE OF INVENTION
The present inventors have long been engaged in intensive investigations in an attempt to discover insecticides quite different in structure from the insecticides that have so far been used. As a result, they unexpectedly found that novel oxadiazolinylpyrazole derivatives represented by the formula [I], inclusive of salts thereof, have very strong insecticidal activity. It was further found that they have little phytotoxicity, are low in toxicity and safe to humans and animals, to fish and to natural enemies to pests, among others. Based on these findings, the present inventors have continued their research, and have now completed the present invention.
Namely, the present invention relates to: [1] a compound represented by the formula [I]:
wherein R
1
is a C
1-6
alkyl group or a C
1-6
haloalkyl group; n is 0, 1 or 2;
X is (1) a group of —NR
2
R
3
wherein R
2
and R
3
independently represent (i) a hydrogen atom or (ii) a C
1-6
alkyl group which may optionally be substituted with pyridyl group,
(2) a group of —N═CHOR
4
wherein R
4
represents a C
1-6
alkyl group,
(3) a group of —N═CHNR
5
R
7
wherein R
6
and R
7
independently represent (i) a hydrogen atom or (ii) a C
1-6
alkyl group,
(4) a group of —N═CHAr wherein Ar represents a phenyl group which may optionally be substituted with a substituent or substituents selected from the group consisting of hydroxy and C
1-3
alkoxy groups, or
(5) a pyrrolyl group;
R
5
is an optionally substituted alkyl group or an optionally substituted acyl group;
R
8
is (1) a halogen atom, (2) a C
1-6
haloalkyl group, (3) a C
1-6
haloalkoxy group or (4) phenyl which may optionally be substituted with a C
1-6
haloalkyl group;
A is (1) a nitrogen atom or (2) a group of
wherein R
9
is a chlorine atom or cyano; and
B is a nitrogen atom or
(hereinafter sometimes referred to as “Compound [I]”); or a salt thereof,
[2] the compound as described in above [1], wherein R
1
is a trifluoromethyl group, or a salt thereof,
[3] the compound as described in above [1], wherein X is (1) a group of —NR
2
R
3
wherein R
2
and R
3
independently represent (i) a hydrogen atom or (ii) a C
1-6
alkyl group, or (2) a group of —N═CHOR
4
wherein R
4
represents a C
1-6
alkyl group, or a salt thereof,
[4] the compound as described in above [1], wherein X is —NH
2
or a group of —N═CHOR
4
wherein R
4
represents a C
1-6
alkyl group, or a salt thereof,
[5] the compound as described in above [1], wherein R
5
is an optionally substituted carbamoyl group, or a salt thereof,
[6] the compound as described in above [1], wherein R
5
is (1) a C
1-6
alkyl group which may optionally be substituted with one to three C
1-6
alkoxy groups, (2) a C
2-10
alkanoyl group which may optionally be substituted with one to three substituents selected from the group consisting of (i) amino which may optionally be substituted with one or two C
1-6
alkyl groups, (ii) a C
1-6
alkoxy group, (iii) phenyl and (iv) a halogen atom, (3) a C
4-10
cycloalkanoyl group, (4) a C
3-10
alkenylcarbonyl group, (5) benzoyl, (6) carbamoyl which may optionally be substituted with one or two substituents selected from the group consisting of (i) a C
1-6
alkyl group which may optionally be substituted with the substituents selected from the group consisting of phenyl, halogen and amino which may optionally be substituted with C
1-6
alkyl, (ii) a C
3-9
cycloalkyl group, (iii) a C
2-6
alkenyl group, (iv) a C
2-6
alkynyl group, (v) phenyl, (vi) amino which may optionally be substituted with one or two C
1-6
alkyl groups, (vii) a cyclic amino group, (viii) hydroxy and (ix) a C
1-6
alkoxy group, (7) a cyclic amino-carbonyl group, or (8) a C
1-6
alkoxy-carbonyl group or (9) formyl, or a salt thereof,
[7] the compound as described in above [1], wherein R
8
is a trifluoromethyl group, or a salt thereof,
[8] the compound as described in above [1], wherein A is
or a salt thereof,
[9] the compound as described in above [1], wherein B is a nitrogen atom, or a salt thereof,
[10] the compound as described in above [1], wherein X is
(1) a group of —NR
2
R
3
wherein R
2
and R
3
independently represent (i) a hydrogen atom or (ii) a C
1-6
alkyl group,
(2) a group of —N═CHOR
4
wherein R
4
represents a C
1-6
alkyl group, or
(3) a group of —N═CHNR
6
R
7
wherein R
6
and R
7
independently represent (i) a hydrogen atom or (ii) a C
1-6
alkyl group;
R
8
is trifluoromethyl;
A is
and
B is a nitrogen atom, or a salt thereof,
[11] the compound as described in above [10], wherein X is (1) a group of —NR
2
R
3
wherein R
2
and R
3
independently represent (i) a hydrogen atom or (ii) a C
1-6
alkyl group, or
(2) a group of —N═CHOR
4
wherein R
4
represents a C
1-6
alkyl group, or a salt thereof,
[12] the compound as described in above [1], which is 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-{4-(N,N-dimethylcarbamoyl)-&Dgr;
2
-1,2,4-oxadiazolin-3-yl}-5-isopropoxymethyleneamino-4-trifluoromethylsulfinylpyrazole or a salt thereof,
[13] the compound as described in above [1], which is 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-{4-(N,N-dimethylcarbamoyl)-&Dgr;
2
-1,2,4-oxadiazolin-3-yl}-5-ethoxymethyleneamino-4-trifluoromethylsulfinylpyrazole or a salt thereof,
[14] the compound as described in above [1], which is 1-(2,6-dichloro-4-trifluoromethylphenyl)-5-ethoxymethyleneamino-3-{4-(morpholinocarbonyl)-&Dgr;
2
-1,2,4-oxadiazolin-3-yl}-4-trifluoromethylsulfinylpyrazole or a salt thereof,
[15] the compound as described in above [1], which is 1-(2,6-dichloro-4-trifluoromethylphenyl)-5-ethoxymethyleneamino-3-{4-isobutylyl-&Dgr;
2
-1,2,4-oxadiazolin-3-yl}-4-trifluoromethylsulfinylpyrazole or a salt thereof,
[16] an agrochemical composition which comprises an effective amount of the compound as described in above [1] or a salt thereof,
[17] the agrochemical composition as described in above [16], which is an insecticidal composition,
[18] a method of combatting an insect, which comprises applying or administering an effective dose of the compound as described in above [1] or a salt thereof to a vertebrate, a paddy field, plowland, orchard, non-cropland or house,
[19] use of the compound as described in above [1] or a salt thereof for the manufacture of an agrochemical composition, and
[20] use of the compound as described in above [1] or a salt thereof for combatting an insect.
BEST MODE FOR CARRYING OUT THE INVENTION
The compound of the above formula [I] or a s
Atsuo Akayama
Kando Yasuyuki
Kiji Toshiyuki
Masada Shinichi
Noguchi Makota
Lambkin Deborah C.
Shameem Golam M. M.
Takeda Chemical Industries Ltd.
Wenderoth , Lind & Ponack, L.L.P.
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