# US 11,998,013 B1 · 1-(morpholin-4-yl)-3-(naphthalen-2-yloxy)propan-2-ol as an eco-friendly insecticidal agent against spodoptera littoralis (boisd.)

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- Number: US 11,998,013 B1
- Document ID: US11998013B1
- Status: Granted
- Kind: B1
- Application number: 18/241,382
- Filed: 2023-09-01
- Granted: 2024-06-04
- Earliest claimed: 2023-09-01
- Assignees: King Faisal University
- Applicants: King Faisal University
- Inventors: Hany Mohamed Abd El-Lateef Ahmed; Mai Mostafa Khalaf Ali; Antar Ahmed Abdelhamid Ahmed; Mohamed A. Gad
- Web page: https://patentgrep.com/patent/US11998013B1

## CPC

- A01N 43/84: six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
- A01N 25/12: Powders or granules (A01N25/26 takes precedence)
- A01N 31/14: Ethers
- A01P 7/04: Insecticides
- C07D 295/088: to an acyclic saturated chain
- 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
- A01P: BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

A compound 1-(morpholin-4-yl)-3-(naphthalen-2-yloxy)propan-2-ol, its synthesis, insecticidal compositions containing the same, and its use as an insecticidal agent.

## Claims

### Claim 1

An insecticidally acceptable composition composing an insecticidally effective amount of a 1-(morpholin-4-yl)-3-(naphthalen-2-yloxy)propan-2-ol compound and an insecticidally acceptable carrier, wherein the 1-(morpholin-4-yl)-3-(naphthalen-2-yloxy)propan-2-ol compound has the formula I:

### Claim 2 (depends on 1)

The insecticidally active composition of claim 1, wherein the compound is obtained as a white powder.

### Claim 3 (depends on 1)

The insecticidally active composition of claim 1, having a melting point of about 112° C. to about 114° C.

### Claim 4 (depends on 1)

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.

### Claim 5 (depends on 4)

The method of killing insects of claim 4, wherein the insects belong to a species Spodoptera littoralis.

### Claim 6 (depends on 5)

The method of killing insects of claim 5, wherein the 1-(morpholin-4-yl)-3-(naphthalen-2-yloxy)propan-2-ol compound has an LC50 of about 17.56 ppm against the species Spodoptera littoralis after 72 hours of treatment.

### Claim 7 (depends on 5)

The method of killing insects of claim 5, wherein the 1-(morpholin-4-yl)-3-(naphthalen-2-yloxy)propan-2-ol compound has an LC50 of about 17.56 ppm against 2nd instars of larvae of the species Spodoptera littoralis after 72 hours of treatment.

### Claim 8 (depends on 5)

The method of killing insects of claim 5, wherein the 1-(morpholin-4-yl)-3-(naphthalen-2-yloxy)propan-2-ol compound has an LC50 of about 69.252 ppm against the species Spodoptera littoralis after 72 hours of treatment.

### Claim 9 (depends on 5)

The method of killing insects of claim 5, wherein the 1-(morpholin-4-yl)-3-(naphthalen-2-yloxy)propan-2-ol compound has an LC50 of about 69.252 ppm against 4th instars of larvae of the species Spodoptera littoralis after 72 hours of treatment.

### Claim 10 (depends on 4)

The method of killing insects of claim 4, wherein the 1-(morpholin-4-yl)-3-(naphthalen-2-yloxy)propan-2-ol compound is applied to castor leaves.

### Claim 11 (depends on 5)

The method of killing insects of claim 5, wherein about 12.5 to about 200 ppm of the 1-(morpholin-4-yl)-3-(naphthalen-2-yloxy)propan-2-ol compound is applied to the insects or to the target site.

### Claim 12 (depends on 1)

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.

### Claim 13 (depends on 12)

The method of repelling insects of claim 12, wherein the insects belong to a species Spodoptera littoralis.

### Claim 14 (depends on 1)

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.

### Claim 15 (depends on 14)

The method of controlling the insect pest of claim 14, wherein the insect pest belongs to a species Spodoptera littoralis.

### Claim 16 (depends on 1)

A method of making the 1-(morpholin-4-yl)-3-(naphthalen-2-yloxy)propan-2-ol compound of claim 1, the method comprising;
treating 2-((2naphthyloxy)methyl)oxirane with morpholine in a presence of triethylamine as a catalyst to obtain a crude product;
purifying the crude product by recrystallization from absolute ethyl alcohol; and
obtaining the 1-(morpholin-4-yl)-3-(naphthalen-2-yloxy)propan-2-ol compound.

### Claim 17 (depends on 16)

The method of making the 1-(morpholin-4-yl)-3-(naphthalen-2-yloxy)propan-2-ol of claim 16, wherein the 1-(morpholin-4-yl)-3-(naphthalen-2-yloxy)propan-2-ol compound is obtained as a white powder.

### Claim 18 (depends on 16)

The method of making the 1-(morpholin-4-yl)-3-(naphthalen-2-yloxy)propan-2-ol compound of claim 16, wherein the 1-(morpholin-4-yl)-3-(naphthalen-2-yloxy)propan-2-ol compound is obtained in an about 60% yield.