# US 5,346,879 A · Plant growth regulator containing a phthalimide derivative

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 5,346,879 A
- Document ID: US5346879A
- Status: Granted
- Kind: A
- Application number: 08/046,836
- Filed: 1993-04-14
- Granted: 1994-09-13
- Earliest claimed: 1989-08-25
- Assignees: Sumitomo Chemical Company, Limited
- Inventors: Akio Manabe; Masato Mizutani; Naonori Hirata; Sachiko Uwayokote; Kazuo Izumi; Kenji Arai
- Web page: https://patentgrep.com/patent/US5346879A

## CPC

- C07D 209/48: with oxygen atoms in positions 1 and 3, e.g. phthalimide
- A01N 37/36: containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- C07C 259/10: having carbon atoms of hydroxamic groups bound to carbon atoms of six-membered aromatic rings
- C07D 207/46: with hetero atoms directly attached to the ring nitrogen atom
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

Plant growth regulators comprising, as an active ingredient, a substituted dicarboxylic acid derivative having the formula: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same as defined in the present specification, the substituted dicarboxylic acid derivatives, and processes for preparing the same, are disclosed. The plant growth regulators provided according to the present invention have a regulating activity on plant growth; more specifically, an action thereof of lowering the content of endogenous ethylene in a plant is utilized.

## Claims

### Claim 1

A plant growth regulator comprising, as an active ingredient, a substituted dicarboxylic acid derivative having the formula: ##STR28## wherein R.sup.1 and R.sup.2 are, same or different, a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a C.sub.1 -C.sub.3 alkyl group or together represent a C.sub.3 -C.sub.5 alkylene group or a divalent organic group represented by the formula, --CH.dbd.CH--CH.dbd.CH--, optionally substituted by X.sub.n to form a cyclic group; R.sup.3 is a hydrogen atom or a C.sub.1 -C.sub.3 alkyl group; and R.sup.4 is a cyano group or a group represented by the formula, --COOR.sup.5, --CH.sub.2 COOR.sup.5 or --CONR.sup.6 R.sup.7, in which X is, same or different, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 alkoxy group, a hydroxyl group, a nitro group or an amino group and n is 0, 1, 2, 3 or 4, R.sup.5 is a hydrogen atom or a C.sub.1 -C.sub.6 alkyl group, R.sup.6 and R.sup.7 are, same or different, a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group or together represent a C.sub.3 -C.sub.5 alkylene group optionally substituted by a methyl group, or physiologically acceptable metal salts or amine salts thereof, and an inert carrier or diluent.

### Claim 2 (depends on 1)

The plant growth regulator according to claim 1, wherein R.sup.1 and R.sup.2 are, same or different, a hydrogen atom, a fluorine atom, a chlorine atom, a C.sub.1 -C.sub.3 alkyl group or together represent a C.sub.3 -C.sub.5 alkylene group or a divalent organic group represented by the formula, --CH.dbd.CH--CH.dbd.CH--, optionally substituted by X.sub.n so as to form a cyclic group; R.sup.3 is a hydrogen atom or a C.sub.1 -C.sub.3 alkyl group; and R.sup.4 is a cyano group or a group represented by the formula, --COOR.sup.5 or --CH.sub.2 COOR.sup.5, in which X is the same or different, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a C.sub.1 -C.sub.4 group, a C.sub.1 -C.sub.4 alkoxy group, a hydroxyl group, a nitro group or an amino group and n is 0, 1, 2, 3 or 4, R.sup.5 is a hydrogen atom or a C.sub.1 -C.sub.6 alkyl group, or physiologically acceptable metal salts or amine salts thereof, and an inert carrier or diluent.

### Claim 3 (depends on 1)

The plant growth regulator according to claim 1, wherein R.sup.1 and R.sup.2 are, same or different, a hydrogen atom, a chlorine atom a C.sub.1 alkyl group or together represent a C.sub.4 alkylene group or a divalent organic group represented by the formula, --CH.dbd.CH--CH.dbd.CH--, optionally substituted by X.sub.n to form a cyclic group; R.sup.3 is a hydrogen atom or a C.sub.1 alkyl group; and R.sup.4 is a cyano group or a group represented by the formula, --COOR.sup.5 or --CH.sub.2 COOR.sup.5, in which X is, same or different, a fluorine atom, a chlorine atom, a C.sub.1 alkyl group, a C.sub.1 alkoxy group, a hydroxyl group or a nitro group and n is 0, 1, 2, 3 or 4, R.sup.5 is a hydrogen atom or a C.sub.1 -C.sub.4 alkyl group, or physiologically acceptable metal salts or amine salts thereof, and an inert carrier or diluent.

### Claim 4 (depends on 1)

The plant growth regulator according to claim 1, wherein R.sup.1 and R.sup.2 are, same or different, a chlorine atom, a C.sub.1 alkyl group or a divalent organic group represented by the formula, --CH.dbd.CH--CH.dbd.CH--, so as to form a cyclic group; R.sup.3 is a hydrogen atom or a C.sub.1 alkyl group; and R.sup.4 is a cyano group or a group represented by the formula, --COOR.sup.5, in which R.sup.5 is a hydrogen atom or a C.sub.1 alkyl group, or physiologically acceptable metal salts or amine salts thereof.

### Claim 5 (depends on 1)

The plant growth regulator according to claim 1, wherein the plant growth regulator lowers the content of endogenous ethylene in a plant.

### Claim 6 (depends on 1)

The plant growth regulator according to claim 1, wherein the plant growth regulator maintains the freshness of cut flowers.

### Claim 7

A method of regulating plant growth, which comprises applying an effective amount of a substituted dicarboxylic acid derivative having the formula: ##STR29## wherein R.sup.1 and R.sup.2 are, same or different, a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a C.sub.1 -C.sub.3 alkyl group or together represent a C.sub.3 -C.sub.5 alkylene group or a divalent organic group represented by the formula, --CH.dbd.CH--CH.dbd.CH--, optionally substituted by X.sub.n to form a cyclic group; R.sup.3 is a hydrogen atom or a C.sub.1 -C.sub.3 alkyl group; and R.sup.4 is a cyano group or a group represented by the formula, --COOR.sup.5, --CH.sub.2 COOR.sup.5 or --CONR.sup.6 R.sup.7, in which X is, same or different, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 alkoxy group, a hydroxyl group, a nitro group or an amino group and n is 0, 1, 2, 3, or 4, R.sup.5 is a hydrogen atom or a C.sub.1 -C.sub.6 alkyl group, R.sup.6 and R.sup.7 are, same or different, a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group or together represent a C.sub.3 -C.sub.5 alkylene group optionally substituted by a methyl group, or physiologically acceptable metal salts or amine salts thereof.

### Claim 8 (depends on 7)

The method according to claim 7, wherein the regulating of plant growth comprises lowering the content of endogenous ethylene in a plant.

### Claim 9 (depends on 7)

The method according to claim 7, wherein the regulating of plant growth comprises maintaining the freshness of cut flowers.

### Claim 10

A substituted dicarboxylic acid derivative having the formula: ##STR30## wherein R.sup.1 and R.sup.2 are, same or different, a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a C.sub.1 -C.sub.3 alkyl group or together represent a C.sub.3 -C.sub.5 alkylene group or a divalent organic group represented by the formula, --CH.dbd.CH--CH.dbd.CH--, substituted by X.sub.n to form a cyclic group; R.sup.3 is a hydrogen atom or a C.sub.1 -C.sub.3 alkyl group; and R.sup.4 is a cyano group or a group represented by the formula, --COOR, --CH.sub.2 COOR.sup.5 or --CONR.sup.6 R.sup.7, in which X is, same or different, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 alkoxy group, a hydroxyl group, a nitro group or an amino group and n is 1, 2, 3 or 4, R.sup.5 is a hydrogen atom or a C.sub.1 -C.sub.6 alkyl group, R.sup.6 and R.sup.7 are, same or different, a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group or together represent a C.sub.3 -C.sub.5 alkylene group optionally substituted by a methyl group, or physiologically acceptable metal salts or amine salts thereof.

### Claim 11 (depends on 10)

The substituted dicarboxylic acid derivative according to claim 10, wherein R.sup.1 and R.sup.2 are, same or different, a hydrogen atom, a fluorine atom, a chlorine atom, a C.sub.1 -C.sub.3 alkyl group or together represent a C.sub.3 -C.sub.5 alkylene group or a divalent organic group represented by the formula, --CH.dbd.CH--CH.dbd.CH--, substituted by X.sub.n so as to form a cyclic group; R.sup.3 is a hydrogen atom or a C.sub.1 -C.sub.3 alkyl group; and R.sup.4 is a cyano group or a group represented by the formula, --COOR.sup.5 or --CH.sub.2 COOR.sup.5, in which X is the same or different, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 alkoxy a group, a hydroxyl group, a nitro group or an amino group and n is 1, 2, 3 or 4, R.sup.5 is a hydrogen atom or a C.sub.1 -C.sub.6 alkyl group, or physiologically acceptable metal salts or amine salts thereof.

### Claim 12 (depends on 10)

The substituted dicarboxylic acid derivative according to claim 10, wherein R.sup.1 and R.sup.2 are, same or different, a hydrogen atom, a chlorine atom, a C.sub.1 alkyl group or together represent a C.sub.4 alkylene group or a divalent organic group represented by the formula, --CH.dbd.CH--CH.dbd.CH--, substituted by X.sub.n to form a cyclic group; R.sup.3 is a hydrogen atom or a C.sub.1 alkyl group; and R.sup.4 is a cyano group or a group represented by the formula, --COOR.sup.5 or --CH.sub.2 COOR.sub.5, in which X is, same or different, a fluorine atom, a chlorine atom, a C.sub.1 alkyl group, a C.sub.1 alkoxy group, a hydroxyl group or a nitro group and n is 1, 2, 3 or 4, R.sup.5 is a hydrogen atom or a C.sub.1 -C.sub.4 alkyl group, or physiologically acceptable metal salts or amine salts thereof.