Agent for controlling diseases and insect pests, containing...

Details Agent for controlling diseases and insect pests, containing... Agent for controlling diseases and insect pests, containing...

2000-01-14

2001-09-18

Owens, Amelia (Department: 1625)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S292000, C504S294000, C549S404000, C549S467000

Reexamination Certificate

active

06291399

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to alkoxyimino-substituted bicyclic derivatives, a process for producing them, agents for controlling diseases and insect pests containing them as an active ingredient, and intermediates of them.
2. Description of the Background
Various compounds usable as agricultural fungicides have been known hitherto. For example, Japanese Patent Unexamined Published Application (hereinafter referred to as “J. P. KOKAI”) No. Hei 4-182461 discloses agricultural fungicides containing alkoxyiminoacetamide compounds as active ingredients. The specific compounds stated in this patent specification include, for example, 2-methoxyimino-2-[2-(indane -5-yloxymethyl)-phenyl]-acetic acid methylamide (compound No. 20).
J. P. KOKAI No. Hei 3-17052 discloses 2-methoxyimino-2-[2-(5,6,7,8-tetrahydronaphthalene-2-yloxymethyl)phenyl]-methylacetate (compound No. 1.246) as a specific example of the compounds:
J. P. KOKAI No. Sho 63-216848 discloses propene derivatives usable for fungicide compositions. Specifically, methyl 3-methoxy-2-[2-(dibenzofuran-2-yloxymethyl)-phenyl]-acrylate (compound No. 189) is given in this patent specification.
It is known that these compounds are effective in controlling diseases (the effects of controlling insect pests are not described in those specifications). However, the derivatives described therein are utterly different from those of the present invention in that they do not have an alkoxyimino substituent in the polycyclic part thereof. Further, these compounds have no or substantially no penetration and translocation. Under these circumstances, it is demanded to provide an agent for controlling diseases, which has an excellent penetration and translocation.
SUMMARY OF THE INVENTION
The object of the present invention is to provide alkoxyimino-substituted bicyclic derivatives having an effect of controlling diseases or insect pests and also an excellent penetration and translocation.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
After intensive investigations on agents for controlling diseases, which have an excellent penetration and translocation, the inventors have found that alkoxyimino-substituted bicyclic derivatives having a specific structure have a high penetration and translocation into plants and an excellent effect of controlling diseases and insect pests. The present invention has been completed on the basis of this finding.
DISCLOSURE OF THE INVENTION
The present invention is as follows:
1. An alkoxyimino-substituted bicyclic derivative having the following formula (I) or salt thereof:
wherein
R
1
represents a hydrogen atom, a C1-C6 alkyl group, a halogenlated C1-C6 alkyl group, a C3-C5 alkenyl group, a halogenated C3-C5 alkenyl group, a C3-C5 alkynyl group, a halogenated C3-C5 alkynyl group, a cyano-C1-C6 alkyl group, a C1-C4 alkoxy-C1-C6 alkyl group, a C1-C4 alkylcarbonyl-C1-C6 alkyl group, a C1-C4 alkoxycarbonyl-C1-C6 alkyl group, a C3-C6 cycloalkyl group, a C3-C6 cycloalkyl-C1-C6 alkyl group, a phenyl-C1-C6 alkyl group, or a naphthyl-C1-C6 alkyl group,
R
2
, R
3
, R
4
and R
5
independently represent a hydrogen atom, a C1-C3 alkyl group or a halogenated C1-C3 alkyl group,
A represents an oxygen atom, a sulfur atom or C(R
6
)R
7
,
R
6
and R
7
independently represent a hydrogen atom, a C1-C3 alkyl group or a halogenated C1-C3 alkyl group,
n represents 0, 1 or 2,
U, V and W independently represent a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a halogenated C1-C6 alkyl group, a C1-C6 alkoxy group, a halogenated C1-C6 alkoxy group, a cyano group or a nitro group,
X and Y independently represent a hydrogen atom, a halogen atom, a C1-C3 alkyl group, a halogenated C1-C3 alkyl group, a C1-C3 alkoxy group, a halogenated C1-C3 alkoxy group, a cyano group or a nitro group,
Z represents C(CO
2
CH
3
)═CHR
8
, C(CO
2
CH
3
)═NOCH
3
, C(CONHCH
3
)═NOCH
3
, C(CSNHCH
3
)═NOCH
3
, N(CO
2
CH
3
)OCH
3
, N(CONHCH
3
)OCH
3
, N(CSNHCH
3
)OCH
3
, CH(CO
2
CH
3
)OCH
3
, CH(CONHCH
3
)OCH
3
or CH(CSNHCH
3
)OCH
3
, and
R
8
represents a hydrogen atom, a methyl group, an ethyl group or a methoxyl group.
2. A process for producing an alkoxyimino-substituted bicyclic derivative having the formula (I) set forth in above item 1, which comprises reacting a phenol having the formula (II):
wherein
R
1
′ represents a C1-C6 alkyl group, a halogenated C1-C6 alkyl group, a C3-C5 alkenyl group, a halogenated C3-C5 alkenyl group, a C3-C5 alkynyl group, a halogenated C3-C5 alkynyl group, a cyano-C1-C6 alkyl group, a C1-C4 alkoxy-C1-C6 alkyl group, a C1-C4 alkylcarbonyl-C1-C6 alkyl group, a C1-C4 alkoxycarbonyl-C1-C6 alkyl group, a C3-C6 cycloalkyl group, a C3-C6 cycloalkyl-C1-C6 alkyl group, a phenyl-C1-C6 alkyl group, or a naphthyl-C1-C6-alkyl group,
R
2
, R
3
, R
4
and R
5
independently represent a hydrogen atom, a C1-C3 alkyl group or a halogenated C1-C3-alkyl group,
A represents an oxygen atom, a sulfur atom or C(R
6
)R
7
,
R
6
and R
7
independently represent a hydrogen atom, a C1-C3 alkyl group or a halogenated C1-C3 alkyl group,
n represents 0, 1 or 2, and
U, V and W independently represent a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a halogenated C1-C6 alkyl group, a C1-C6 alkoxy group, a halogenated C1-C6 alkoxy group, a cyano group or a nitro group,
with a phenyl compound having the formula (III):
wherein
X and Y independently represent a hydrogen atom, a halogen atom, a C1-C3 alkyl group, a halogenated C1-C3 alkyl group, a C1-C3 alkoxy group, a halogenated C1-C3 alkoxy group, a cyano group or a nitro group,
L represents a leaving group,
Z represents C(CO
2
CH
3
)═CHR
8
, C(CO
2
CH
3
)═NOCH
3
, C(CONHCH
3
)═NOCH
3
, C(CSNHCH
3
)═NOCH
3
, N(CO
2
CH
3
)OCH
3
, N(CONHCH
3
)OCH
3
, N(CSNHCH
3
)OCH
3
, CH(CO
2
CH
3
)OCH
3
, CH(CONHCH
3
)OCH
3
or CH(CSNHCH
3
)OCH
3
, and
R
8
represents a hydrogen atom, a methyl group, an ethyl group or a methoxy group.
3. A process for producing an alkoxyimino-substituted bicyclic derivative having the formula (I) set forth in above item 1, which comprises reacting a substituted bicyclic compound having the formula (IV):
wherein
R
2
, R
3
, R
4
and R
5
independently represent a hydrogen atom, a C1-C3 alkyl group or a halogenated C1-C3 alkyl group,
A represents an oxygen atom, a sulfur atom or C(R
6
)R
7
,
R
6
and R
7
independently represent a hydrogen atom, a C1-C3 alkyl group or a halogenated C1-C3 alkyl group,
n represents 0, 1 or 2,
U, V and W independently represent a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a halogenated C1-C6 alkyl group, a C1-C6 alkoxy group, a halogenated C1-C6 alkoxy group, a cyano group or a nitro group,
X and Y independently represent a hydrogen atom, a halogen atom, a C1-C3 alkyl group, a halogenated C1-C3 alkyl group, a C1-C3 alkoxy group, a halogenated C1-C3 alkoxy group, a cyano group or a nitro group,
Z represents C(CO
2
CH
3
)═CHR
8
, C(CO
2
CH
3
)═NOCH
3
, C(CONHCH
3
)═NOCH
3
, C(CSNHCH
3
)═NOCH
3
, N(CO
2
CH
3
)OCH
3
, N(CONHCH
3
)OCH
3
, N(CSNHCH
3
)OCH
3
, CH(CO
2
CH
3
)OCH
3
, CH(CONHCH
3
)OCH
3
or CH(CSNHCH
3
)OCH
3
, and
R
8
represents a hydrogen atom, a methyl group, an ethyl group or a methoxy group, with an amine having the formula (V) or a salt thereof:
R
1
ONH
2
  (V)
wherein R
1
represents a hydrogen atom, a C1-C6 alkyl group, a halogenated C1-C6 alkyl group, a C3-C5 alkenyl group, a halogenated C3-C5 alkenyl group, a C3-C5 alkynyl group, a halogenated C3-C5 alkynyl group, a cyano-C1-C6 alkyl group, a C1-C4 alkoxy-C1-C6 alkyl group, a C1-C4 alkylcarbonyl-C1-C6 alkyl group, a C1-C4 alkoxycarbonyl-C1-C6 alkyl group, a C3-C6 cycloalkyl group, a C3-C6 cycloalkyl-C1-C6 alkyl group, a phenyl-C1-C6 alkyl group, or a naphthyl-C1-C6 alkyl group.
4. An agent for controlling a disease or an insect pest, comprising the alkoxyimino-substituted bicyclic derivative or salt thereof set forth in above item 1 as an active ingredient.
5. An intermediate having the following formula (II):
whe

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