US 10,208,033 B2 · β-carboline, dihydro-β-carboline and tetrahydro-β-carboline alkaloid derivatives and preparation methods same and use in aspects of preventing and treating plant viruses, fungicides and insecticides

Abstract

The present invention relates to β-carboline, dihydro-β-carboline and tetrahydro-β-carboline alkaloid derivatives (I) and a method for preparing same and the use in the aspects of preventing and treating plant viruses, fungicides and insecticides. For the meaning of each group in formula (I) see the description. The β-carboline, dihydro-β-carboline and tetrahydro-β-carboline alkaloid derivatives of the present invention show a particularly ourstanding anti-plant virus activity, and also have fungicidal and insecticidal activities.

Claims9

Dependent claims

A β-carboline compound with a structure shown in the following formula Ic or formula Id

wherein,
R4 and R5 respectively represent hydrogen, C1-C10 alkyl, C3-C10 nitrogen-containing heterocyclic ring, C1-C10 oxygen-containing heterocyclic ring, or C1-C10 sulfur-containing heterocyclic ring, or R4 and R5 form a C6 aliphatic ring, or R4 is hydrogen and R5 is prop-2-enyl;
and
R6 represents hydrogen, hydroxy, C1-C6 alkoxy, substituted phenyl ring, C1-C10 oxygen-containing heterocyclic ring, or C1-C10 sulfur-containing heterocyclic ring.

1 more element

A β-carboline compound selected from the group consisting of:

(1S, 3S)—N′-benzylidene-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-1);
(1S, 3S)—N′-(4-tert-butyl benzylidene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-2);
(1S, 3S)—N′-(4-dimethyl amino benzylidene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-3);
(1S, 3S)—N′-(4-nitrobenzylidene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-4);
(1S, 3S)—N′-(4-chlorobenzylidene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-5);
(1S, 3S)—N′-(2, 4-dichlorobenzylidene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-6);
(1S, 3S)—N′-(3,4-dichlorobenzylidene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-7);
(1S, 3S)—N′-(4-methoxybenzylidene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-8);
(1S, 3S)—N′-(3-methoxybenzylidene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-9);
(1S, 3S)—N′-(2-methoxybenzylidene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-10);
(1S, 3S)—N′-(3,4-dimethoxybenzylidene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-11);
(1S, 3S)—N′-((benzo [d] [1, 3] dioxymethylene-5)-methylene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-12);
(1S, 3S)—N′-(2, 3-dihydrobenzo [b] [1, 4] dioxin-6-methylene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-13);
(1S, 3S)—N′-(6-hydroxynaphthalene-2-methylene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-14);
(1S, 3S)—N′-(pyridine-4-methylene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-15);
(1S, 3S)—N′-(pyridine-3-methylene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-16);
(1S, 3S)—N′-(pyridine-2-methylene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-17);
(1S, 3S)—N′-(furan-2-methylene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-18);
(1S, 3S)—N′-(pyrrole-2-methylene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-19);
(1S, 3S)—N′-(thiophene-2-methylene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-20);
(1S, 3S)—N′-(imidazole-2-methylene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-21);
(1S, 3S)—N′-((E)-but-2-enylidene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-22);
(1S, 3S)—N′-butylidene-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-23);
(1S, 3S)—N′-octadien-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-24);
(1S, 3S)—N′-(cyclohexylmethylene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-25);
(1S, 3S)—N′-(2,2-dimethylpropylidene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-26);
(1S, 3S)—N′-(1-phenylethylidene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-27);
(1S, 3S)—N′-(3,3-dimethyl-2-butylidene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-28);
(1S, 3S)—N′-cyclohexylidene-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-29);
N′-((1S, 3S)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-tricarboxylate) benzo [d] [1,2,3] thiadiazole-7-formylhydrazine (Id-i);
4-methyl-N′-((1S, 3S)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-triformyl)-1, 2, 3-thiadiazole-5-formylhydrazine (Id-2);
(1S, 3S)—N′-isonicotinoyl-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Id-3);
(1S, 3S)—N′-benzoyl-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Id-4);
(1S, 3S)—N′-n-hexanoyl-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Id-5);
(1S, 3S)—N′-tert-valeryl-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Id-G);
and
(1S, 3S)—N′-(cyclopentyl formyl)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Id-7).

34 more elements

A method of treating plant viruses comprising administering a β-carboline compound selected from the group consisting of:

(1S, 3S)—N′-benzylidene-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-1);
(1S, 3S)—N′-(4-tert-butyl benzylidene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-2);
(1S, 3S)—N′-(4-dimethyl amino benzylidene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-3);
(1S, 3S)—N′-(4-nitrobenzylidene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-4);
(1S, 3S)—N′-(4-chlorobenzylidene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-5);
(1S, 3S)—N′-(2, 4-dichlorobenzylidene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-6);
(1S, 3S)—N′-(3,4-dichlorobenzylidene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-7);
(1S, 3S)—N′-(4-methoxybenzylidene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-8);
(1S, 3S)—N′-(3-methoxybenzylidene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-9);
(1S, 3S)—N′-(2-methoxybenzylidene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-10);
(1S, 3S)—N′-(3,4-dimethoxybenzylidene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-11);
(1S, 3S)—N′-((benzo [d] [1, 3] dioxymethylene-5)-methylene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-12);
(1S, 3S)—N′-(2, 3-dihydrobenzo [b] [1, 4] dioxin-6-methylene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-13);
(1S, 3S)—N′-(6-hydroxynaphthalene-2-methylene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-14);
(1S, 3S)—N′-(pyridine-4-methylene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-15);
(1S, 3S)—N′-(pyridine-3-methylene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-16);
(1S, 3S)—N′-(pyridine-2-methylene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-17);
(1S, 3S)—N′-(furan-2-methylene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-18);
(1S, 3S)—N′-(pyrrole-2-methylene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-19);
(1S, 3S)—N′-(thiophene-2-methylene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-20);
(1S, 3S)—N′-(imidazole-2-methylene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-21);
(1S, 3S)—N′-((E)-but-2-enylidene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-22);
(1S, 3S)—N′-butylidene-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-23);
(1S, 3S)—N′-octadien-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-24);
(1S, 3S)—N′-(cyclohexylmethylene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-25);
(1S, 3S)—N′-(2,2-dimethylpropylidene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-26);
(1S, 3S)—N′-(1-phenylethylidene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-27);
(1S, 3S)—N′-(3,3-dimethyl-2-butylidene)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-28);
(1S, 3S)—N′-cyclohexylidene-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Ic-29);
N′-((1S, 3S)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-tricarboxylate) benzo [d] [1,2,3] thiadiazole-7-formylhydrazine (Id-1);
4-methyl-N′-((1S, 3S)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-triformyl)-1, 2, 3-thiadiazole-5-formylhydrazine (Id-2);
(1S, 3S)—N′-isonicotinoyl-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Id-3);
(1S, 3S)—N′-benzoyl-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Id-4);
(1S, 3S)—N′-n-hexanoyl-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Id-5);
(1S, 3S)—N′-tert-valeryl-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-f ormylhydrazine (Id-6);
and
(1S, 3S)—N′-(cyclopentyl formyl)-1-methyl-2,3,4,9-tetrahydropyridino [3,4-b] indol-3-formylhydrazine (Id-7).

34 more elements

Dependencies are inferred from the claim text.

Facts

Application

15/109,371Filed 24 Dec 2014

Priority

CN 2013 1 075224030 Dec 2013

Published

US 2016/0326166 A110 Nov 2016

Granted

19 Feb 2019

Term ends

Not estimatedThe source records don’t support an estimate.

Classification4 codes

C07D 471/04
In which the condensed system contains two hetero rings: ortho-condensed systems
A01N 43/90
Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds: having two or more relevant hetero rings,…
C07D
Heterocyclic compounds
A01N
Preservation of bodies of humans or animals or plants or parts thereof

Abstract

Facts

Application

15/109,371Filed 24 Dec 2014

Priority

CN 2013 1 075224030 Dec 2013

Published

US 2016/0326166 A110 Nov 2016

Granted

19 Feb 2019

Term ends

Not estimatedThe source records don’t support an estimate.

Classification4 codes

C07D 471/04
In which the condensed system contains two hetero rings: ortho-condensed systems
A01N 43/90
Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds: having two or more relevant hetero rings,…
C07D
Heterocyclic compounds
A01N
Preservation of bodies of humans or animals or plants or parts thereof

β-carboline, dihydro-β-carboline and tetrahydro-β-carboline alkaloid derivatives and preparation methods same and use in aspects of preventing and treating plant viruses, fungicides and insecticides

Life of this patent

Abstract

Claims9

β-carboline, dihydro-β-carboline and tetrahydro-β-carboline alkaloid derivatives and preparation methods same and use in aspects of preventing and treating plant viruses, fungicides and insecticides

Life of this patent

Abstract

Claims9