# US 5,348,976 A · Condensed heterocyclic derivatives and agricultural or horticultural fungicides containing the same

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- Number: US 5,348,976 A
- Document ID: US5348976A
- Status: Granted
- Kind: A
- Application number: 08/117,284
- Filed: 1993-09-07
- Granted: 1994-09-20
- Earliest claimed: 1992-09-07
- Assignees: Kumai Chemical Industry Co., Ltd.; Ihara Chemical Industry Co., Ltd.
- Inventors: Masaru Shibata; Shigekazu Ito; Jun-etsu Sakai; Shigeru Hayashi
- Web page: https://patentgrep.com/patent/US5348976A

## CPC

- A01N 43/42: condensed with carbocyclic rings
- A01N 43/12: condensed with a carbocyclic ring
- A01N 43/14: six-membered rings
- A01N 43/38: condensed with carbocyclic rings
- A01N 47/12: containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
- A01N 47/14: Di-thio analogues thereof
- A01N 47/18: containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
- A01N 47/22: O-Aryl or S-Aryl esters thereof
- A01N 47/28: Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< (isoureas, isothioureas A01N47/42)
- A01N 47/30: Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
- C07D 209/14: Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C07D 215/12: with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D 307/81: Radicals substituted by nitrogen atoms not forming part of a nitro radical
- C07D 333/58: Radicals substituted by nitrogen atoms
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present invention provides a condensed heterocyclic derivative represented by a formula: ##STR1## wherein R.sup.1 represents a lower alkyl group, an alkenyl group, or the like, R.sup.2, R.sup.3, R.sup.4, R.sup.5, and R.sup.6 independently represent a hydrogen atom, a lower alkyl, or the like, W is represented by --OC(O)--, --SC(O)--, or the like, and Z represents a 2-indolyl group or the like. The present invention also provides an agricultural or horticultural fungicide which comprises an amount of the condensed derivative known to be effective as a fungicide. The agricultural or horticultural fungicide according to the present invention exhibits a superior control effect for downy mildew and late blight, without harm to nonfungal, photosynthesizing plants.

## Claims

### Claim 1

A condensed heterocyclic derivative represented by a formula: ##STR26## wherein R.sup.1 represents a C1-C6 alkyl group optionally having at least one substituent selected from the group consisting of a halogen atom, a cyano group, and a methoxy group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C8 cycloalkyl group optionally having at least one methyl group, a C3-C8 cycloalkenyl group optionally having at least one methyl group, a C2-C6 cyclic ether group optionally having at least one methyl group, a C7-C10 aralkyl group optionally having at least one substituent selected from the group consisting of a methyl group, a methoxy group, and a nitro group, a phenyl group optionally having at least one substituent selected from the group consisting of a halogen atom, a methyl group, a methoxy group, a nitro group, and a methoxycarbonyl group, a dimethylamino group, or an ethoxy carbonyl group,
R.sup.2, R.sup.3, R.sup.4, R.sup.5, and R.sup.6 independently represent a hydrogen atom, a C1-C6 alkyl group optionally having at least one halogen group, a C3-C6 cycloalkyl group, a C7-C10 aralkyl group; a phenyl group, a cyano group, an acyl group, a C1-C6 alkoxy group, or a C1-C6 alkoxycarbonyl group,
R.sup.2 may form a C3-C6 alkylic ring with R.sup.3 ;
Z is represented by the following formulae: ##STR27## wherein X represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group optionally having at least one halogen atom, a C2-C6 alkynyl group, a methoxy group, a trifluoromethoxy group, a hydroxyl group, a methoxycarbonyl group, a methylcarbonyloxy group, an amino group, a dimethylamino group, a nitro group, a methylthio group, a methylsulfinyl group, a methylsulfonyl group, a phenyl group, an acetyl group, a formyl group, or a cyano group;
n is an integer of 1, 2, or 3;
A is O, S, N, or represented by the formula: ##STR28## wherein R.sup.7 represents a hydrogen atom, a methyl group, an acetyl group, or a benzoyl group; and
W is represented by --C(O)--, --SO.sub.2 --, --NHC(O)--, --N(CH.sub.3)C(O)--, --OC(O)--, --SC(O)--, --OC(S)--, or --SC(S)--.

### Claim 2 (depends on 1)

A condensed heterocyclic derivative as recited in claim 1, wherein
R.sup.1 represents a C2-C6 straight or branched alkyl group, a C3 straight or branched alkenyl group, a C5-C6 cycloalkyl group, or a phenyl group,
R.sup.2 represents a hydrogen atom,
R.sup.3 represents an ethyl group, an isopropyl group, or a sec-butyl group,
R.sup.4 represents a hydrogen atom, a methyl group, an ethyl group, or a phenyl group,
R.sup.5 represents a hydrogen atom, or a methyl group,
R.sup.6 represents a hydrogen atom,
Z represents a substituted heterocyclic group including a benzofuran group, a benzothiophene group, an indole group, or a 2,3-dihydrobenzofuran which has one or two substituent selected from the group consisting of a fluorine atom, a chlorine atom, a nitro group, a cyano group, and a methyl group,
W is represented by --OC(O)--, and
wherein the carbon to which R.sup.2 and R.sup.3 are attached is in the S configuration.

### Claim 3 (depends on 1)

A condensed heterocyclic derivative as recited in claim 1, wherein
R.sup.1 represents an isopropyl group, a tert-butyl group, a sec-butyl group, a cyclopentyl group, an isopropenyl group, or a phenyl group,
R.sup.2 represents a hydrogen atom,
R.sup.3 represents an ethyl group, an isopropyl group, or a sec-butyl group,
R.sup.4 represents a methyl group,
R.sup.5 represents a hydrogen atom,
R.sup.6 represents a hydrogen atom,
Z represents a substituted heterocyclic group including a benzofuran group or a benzothiophene which has one or two substituent selected from the group consisting of a fluorine atom, a chlorine atom, a nitro group, a cyano group, and a methyl group,
W is represented by --OC(O)--, and
wherein the carbon to which R.sup.2 and R.sup.3 are attached is in the S configuration.

### Claim 4 (depends on 1)

A condensed heterocyclic derivative as recited in claim 1, wherein the derivative includes N.sup.1 -[1-(5-chloro-2-benzofuranyl)ethyl]-N.sup.2 -cyclopentyloxycarbonyl-L-valinamide, N.sup.1 -[1-(5-chloro-2-benzofuranyl)ethyl]-N.sup.2 -isopropyloxycarbonyl-L-valinamide, N.sup.1 -[1-(5-fluoro-2-benzofuranyl)ethyl]-N.sup.2 -isopropyloxycarbonyl-L-valinamide, N.sup.2 -isopropyloxycarbonyl-N.sup.1 -[1-(5-nitro-2-benzofuranyl)ethyl]-L-valinamide, N.sup.1 -[1-(5-fluoro-2-benzo[b]thienyl)ethyl]-N.sup.2 -isopropyloxycarbonyl-L-valinamide, N.sup.1 -[1-(6-fluoro-2-benzo[b]thienyl)ethyl]-N.sup.2 -isopropyloxycarbonyl-L-valanimide, N.sup.2 -sec-butyloxycarbonyl-N.sup.1 -[1-(5-chloro-2-benzofuranyl)ethyl]-L-valinamide, or N.sup.1 -[1-(5-chloro-2-benzofuranyl)ethyl]-N.sup.2 -phenoxycarbonyl-L-valinamide.

### Claim 5 (depends on 1)

An agricultural or horticultural fungicide which comprises an effective amount of a condensed heterocyclic derivative, as recited in claim 1, known to be effective as a fungicide and a diluent.

### Claim 6 (depends on 1)

A method for controlling fungi which infect agricultural or horticultural nonfungal, photosynthetic plants comprising the step of applying an effective amount of a condensed heterocyclic derivative, as recited in claim 1, known to be effective as a fungicide to the plants.