1-(butyl(2-hydroxy-3-(naphthalen-1-yloxy)propyl)amino)-3-(naphthalen-2-yloxy)propan-2-ol as an eco-friendly insecticidal agent against Spodoptera littoralis (boisd.)

Patent metadata

Field	Value
Publication number	US-11903385-B1
Application number	US-202318388732-A
Country	US
Kind code	B1
Filing date	Nov 10, 2023
Priority date	Nov 10, 2023
Publication date	Feb 20, 2024
Grant date	Feb 20, 2024

Abstract

Synthesis of a compound 1-(butyl(2-hydroxy-3-(naphthalen-1-yloxy)propyl)amino)-3-(naphthalen-2-yloxy)propan-2-ol and its use as an insecticidal agent.

First claim

We claim:

1. An insecticidally acceptable composition comprising an insecticidally effective amount of a 1-(butyl(2-hydroxy-3-(naphthalen-1-yloxy)propyl)amino)-3-(naphthalen-2-yloxy)propan-2-ol compound having the formula I:

2. A method of killing insects comprising applying to said insects or to a target site of insect infestation an insecticidally effective amount of the insecticidally active composition of claim 1 .

3. The method of killing insects of claim 2 , wherein the insects belong to a species Spodoptera littoralis.

4. The method of killing insects of claim 3 , wherein the 1-(butyl(2-hydroxy-3-(naphthalen-1-yloxy)propyl)amino)-3-(naphthalen-2-yloxy)propan-2-ol compound has an LC 50 of about 10.76 mg/L against the species Spodoptera littoralis after 72 hours of treatment.

5. The method of killing insects of claim 3 , wherein the 1-(butyl(2-hydroxy-3-(naphthalen-1-yloxy)propyl)amino)-3-(naphthalen-2-yloxy)propan-2-ol compound has an LC 50 of about 10.76 mg/L against 2 nd instars of larvae of the species Spodoptera littoralis after 72 hours of treatment.

6. The method of killing insects of claim 3 , wherein the 1-(butyl(2-hydroxy-3-(naphthalen-1-yloxy)propyl)amino)-3-(naphthalen-2-yloxy)propan-2-ol compound has an LC 50 of about 16.65 mg/L against 4 th instars of larvae of the species Spodoptera littoralis after 72 hours of treatment.

7. The method of killing insects of claim 2 , wherein the 1-(butyl(2-hydroxy-3-(naphthalen-1-yloxy)propyl)amino)-3-(naphthalen-2-yloxy)propan-2-ol compound is applied to castor leaves.

8. The method of killing insects of claim 2 , wherein about 12.5 to about 1000 ppm of the 1-(butyl(2-hydroxy-3-(naphthalen-1-yloxy)propyl)amino)-3-(naphthalen-2-yloxy)propan-2-ol compound is applied to the insects or to the target site.

9. A method of repelling insects comprising applying to a target site of insect infestation an insect repelling effective amount of the insecticidally active composition of claim 1 .

10. The method of repelling insects of claim 9 , wherein the insects belong to a species Spodoptera littoralis.

11. A method of controlling an insect pest comprising applying to a target site of insect infestation an insect controlling effective amount of the insecticidally active composition of claim 1 .

12. The method of controlling the insect pest of claim 11 , wherein the insect pest belongs to a species Spodoptera littoralis.

13. A method of making a 1-(butyl(2-hydroxy-3-(naphthalen-1-yloxy)propyl)amino)-3-(naphthalen-2-yloxy)propan-2-ol compound, the method comprising:
adding triethanolamine (TEA) dropwise to a mixture of 2-((naphthalen-1-yloxy)methyl)oxirane and butan-1-amine in ethanol to obtain a reaction mixture;
irradiating the reaction mixture;
cooling the reaction mixture to room temperature;
purifying a precipitating product by crystallization using dioxane; and
obtaining the 1-(butyl(2-hydroxy-3-(naphthalen-1-yloxy)propyl)amino)-3-(naphthalen-2-yloxy)propan-2-ol compound.

14. The method of making the 1-(butyl(2-hydroxy-3-(naphthalen-1-yloxy)propyl)amino)-3-(naphthalen-2-yloxy)propan-2-ol compound of claim 13 , wherein the irradiating step is conducted in an MW oven for about 5 minutes.

15. The method of making the 1-(butyl(2-hydroxy-3-(naphthalen-1-yloxy)propyl)amino)-3-(naphthalen-2-yloxy)propan-2-ol compound of claim 13 , wherein the 1-(butyl(2-hydroxy-3-(naphthalen-1-yloxy)propyl)amino)-3-(naphthalen-2-yloxy)propan-2-ol compound is obtained in an about 73% yield.

Assignees

• Univ King Faisal

Inventors

• Ali Mai Mostafa Khalaf
• Ahmed Hany Mohamed Abd El-Lateef
• Ahmed Antar Ahmed Abdelhamid
• Amer Amer A
• Gad Mohamed A

Classifications

• A01N33/10 Primary

  having at least one oxygen or sulfur atom directly attached to an aromatic ring system · CPC title

• A01P7/04

  Insecticides · CPC title

• A01P17/00

  Pest repellants · CPC title

• C07C213/08

  by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups · CPC title

• C07C213/10

  Separation; Purification; Stabilisation; Use of additives · CPC title