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