# US 11,076,597 B2 · High stress resistant plant growth regulator and preparation method and use thereof

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- Number: US 11,076,597 B2
- Document ID: US11076597B2
- Status: Granted
- Kind: B2
- Application number: 16/066,755
- Filed: 2016-11-18
- Published: 2019-01-03
- Granted: 2021-08-03
- Earliest claimed: 2015-12-28
- Assignees: Cas Center for Excellence In Molecular Plant Sciences
- Applicants: Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences
- Inventors: Jiankang Zhu; Yulu Zhang; Minjie Cao; Xue Liu; Qiuhua Wang
- Web page: https://patentgrep.com/patent/US11076597B2

## CPC

- A01N 43/86: six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N 43/42: condensed with carbocyclic rings
- A01N 43/54: 1,3-Diazines; Hydrogenated 1,3-diazines
- C07D 215/227: only one oxygen atom which is attached in position 2
- C07D 215/38: Nitrogen atoms (nitro radicals C07D215/18)
- C07D 239/80: Oxygen atoms
- C07D 263/58: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D 265/18: with hetero atoms directly attached in position 2
- C07B 2200/07: Optical isomers
- 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)
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

Disclosed are a high stress resistant plant growth regulator and a preparation and use thereof. In particular, the compound provided by the present invention is an ABA substitute for significantly improving the stress resistance of plants, and therefore has a very wide application prospect.

## Claims

### Claim 1

A compound represented by formula (I), or a salt, or an optical isomer or a racemate, or a solvate, thereof,
wherein,
R1 is H, halogen, C1-C3 alkyl, or C1-C3 haloalkyl;
R2 is H, halogen, C1-C3 alkyl, or C1-C3 haloalkyl;
R3 is H, halogen, C1-C3 alkyl, or C1-C3 haloalkyl;
R4 is H, halogen, C1-C3 alkyl, or C1-C3 haloalkyl;
R5 is halogen, C1-C3 alkyl, C1-C3 haloalkyl, SF5 or C3-C8 cycloalkyl;
R6 is substituted or unsubstituted C1-C7 alkyl, substituted or unsubstituted C2-C7 alkenyl, substituted or unsubstituted C2-C7 alkynyl, substituted or unsubstituted C3-C7 cycloalkyl, or substituted or unsubstituted —Ra—O—Rb, wherein Ra is C1-C2 alkylene and Rb is H, C1-C3 alkyl; and substituted means substituted with one or more substituents selected from the group consisting of: halogen, —ORb, —CN, —N(Rb)2, and nitro;
R7 is selected from the group consisting of: H, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C2-C6 alkynyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C5-C10 heterocyclyl, Rc—C(O)—, —ORb, —CN, and —N(Rb)2; Rc is selected from the group consisting of: hydroxyl, mercapto, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C1-C6 alkoxy; wherein the heterocyclyl contains 1 to 2 heteroatoms selected from N, O, S, and substituted means substituted with one or more substituents selected from the group consisting of: halogen, —ORb, —CN, —N(Rb)2, and nitro;
R8, R9, R10 are each independently selected from the group consisting of:
(i) H;
(ii) substituted or unsubstituted C1-C6 alkyl, C3-C8 alkoxy, substituted or unsubstituted C3-C8 cycloalkyl, halogen, Rc—C(O)—, —OH, —NH2; R11 is selected from the group consisting of: hydroxyl, mercapto, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C1-C6 alkoxy; wherein substituted means substituted with one or more substituents selected from the group consisting of: halogen, —ORb, —CN, —N(Rb)2, and nitro;
R11 is H, C1-C3 alkyl, or C1-C3 haloalkyl;
X is NR13, O, or S, R13 is none, or selected from the group consisting of: H, halogen, C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkenyl, and C1-C3 haloalkyl;
m=1 or 2;
“” represents a single bond or a double bond.

### Claim 2 (depends on 1)

The compound of claim 1, wherein the compound has a structure of formula Ia:

### Claim 3 (depends on 1)

The compound of claim 1, wherein the compound has a structure of formula Ib:

### Claim 4 (depends on 1)

The compound of claim 1, wherein the compound has a structure of formula Ic:

### Claim 5 (depends on 1)

The compound of claim 1, wherein the compound is selected from the group consisting of:

### Claim 6 (depends on 1)

An agricultural formulation which comprises:
(i) a compound represented by formula (I), or a salt, or an optical isomer, or a racemate, or a solvate thereof of claim 1; and
(ii) an agriculturally acceptable carrier.

### Claim 7 (depends on 1)

The compound represented by formula (I) of claim 1, wherein the compound is selected from the group consisting of: