# US 12,108,762 B2 · Methods of controlling crop pests using aromatic amide insect repellents, methods of making aromatic amide insect repellents, and novel aromatic amide insect repellents

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- Number: US 12,108,762 B2
- Document ID: US12108762B2
- Status: Granted
- Kind: B2
- Application number: 17/377,022
- Filed: 2021-07-15
- Published: 2022-03-10
- Granted: 2024-10-08
- Earliest claimed: 2020-09-08
- Applicants: Santanu Maitra; David Lent; Jacob Guerra; Peter Robles
- Inventors: Santanu Maitra; David Lent; Jacob Guerra; Peter Robles
- Web page: https://patentgrep.com/patent/US12108762B2

## CPC

- A01N 43/60: 1,4-Diazines; Hydrogenated 1,4-diazines
- A01N 25/04: Dispersions, {emulsions, suspoemulsions, suspension concentrates} or gels (foams A01N25/16)
- A01N 43/36: five-membered rings
- A01N 43/40: six-membered rings
- A01P 7/04: Insecticides
- 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

## Abstract

Methods of protecting fruit crops from flying insect pests and of repelling flying insects using aromatic amide compounds are disclosed. The methods apply the compounds to various surfaces, such as the fruit crops, the ground or structures adjacent to the fruit crops, or an object, article, human skin or animal. The compounds have the formula RxC6Hy—C(═O)—N(Cy), where RxC6Hy is a substituted phenyl group, each R group is independently C1-C6 alkyl, substituted C1-C4 alkyl, (substituted) C6-C10 aryl, C1-C4 alkoxy, C6-C10 aryloxy, halogen, nitro, cyano, cyanate, isocyanate, nitroso, C1-C4 alkylthio, phenylthio, (halogen-substituted) C1-C4 alkylsulfonyl, phenylsulfonyl, tolylsulfonyl, amino, mono- or di-C1-C4 alkylamino, diphenylamino, di-C1-C4 alkylamido, formyl, C2-C7 acyl, or C1-C6 alkoxycarbonyl; x is an integer of 1 to 5; x+y=5; Cy is a C2-C8 (substituted) alkadiyl, a C4-C6 (substituted) alkenediyl, or a (substituted) diyl of the formula —(CH2CH2)—O—(CH2CH2)—, —(CH2CH2)—NR′—(CH2CH2)— or —(CH2CH2)—S—(CH2CH2)— that, along with the amide N atom, forms a non-aromatic cyclic group; and R′ is C1-C6 alkyl, substituted C1-C4 alkyl, (substituted) C6-C10 aryl, or (substituted) benzyl.

## Claims

### Claim 1

A method of protecting fruit crops from flying insect pests, comprising applying a compound having a formula RxC6Hy—C(═O)—N(Cy) to the fruit crops or to ground or structures adjacent to the fruit crops, wherein:
RxC6Hy is a substituted phenyl group,
each R group is independently selected from C1-C6 alkyl, C1-C4 alkyl substituted with 1 to 2n+1 halogen atoms (where n=the number of C atoms in the C1-C4 alkyl group) or a C1-C4 alkoxy group, C6-C10 aryl, C6-C10 aryl substituted with 1-5 halogen atoms or 1 or 2 C1-C4 alkoxy groups, C1-C4 alkoxy, C6-C10 aryloxy, halogen, nitro, cyano, cyanate, isocyanate, nitroso, C1-C4 alkylthio, phenylthio, unsubstituted C1-C4 alkylsulfonyl, C1-C4 alkylsulfonyl substituted with 1 to 2n+1 halogen atoms, phenylsulfonyl, tolylsulfonyl, amino, mono-C1-C4 alkylamino, di-C1-C4 alkylamino, diphenylamino, di-C1-C4 alkylamido, formyl, C2-C7 acyl, or C1-C6 alkoxycarbonyl;
x is an integer of from 1 to 5 and x+y=5;
Cy is a C2-C8 substituted or unsubstituted alkadiyl or a substituted or unsubstituted diyl of the formula —(CH2CH2)—O—(CH2CH2)—, —(CH2CH2)—NR′—(CH2CH2)— or —(CH2CH2)—S—(CH2CH2)—, that, along with the N atom in the amide group in the formula, forms a substituted or unsubstituted non-aromatic cyclic group; and
R′ is C1-C6 alkyl, substituted C1-C4 alkyl, substituted or unsubstituted C6-C10 aryl, or substituted or unsubstituted benzyl.

### Claim 2 (depends on 1)

The method of claim 1, wherein the compound is applied to the fruit crops.

### Claim 3 (depends on 1)

The method of claim 1, wherein the compound is applied by spraying a solution or suspension of the compound on the fruit crops, the ground, or the structures.

### Claim 4 (depends on 1)

The method of claim 1, wherein x is 1 or 2.

### Claim 5 (depends on 1)

The method of claim 1, wherein Cy, together with the N atom in the —C(═O)—N group, forms a mono- or polycyclic heterocycle selected from pyrrolidine, pyrimidine, 1,2,3-trihydroindole, 1,2,3-tetrahydroisoquinoline, decahydroquinoline, decahydroisoquinoline, tetrahydropyrazine, morpholine, thiomorpholine, hexahydroazepine, azocane and azonane.

### Claim 6 (depends on 5)

The method of claim 5, wherein Cy, together with the N atom in the —C(═O)—N group, forms a pyrrolidine, pyrimidine, tetrahydropyrazine, or morpholine ring.

### Claim 7 (depends on 1)

The method of claim 1, wherein Cy is unsubstituted.

### Claim 8 (depends on 4)

The method of claim 4, wherein each R is C1-C6 alkyl, C1-C4 alkyl substituted with 1 to 2n+1 halogen atoms (where n=the number of C atoms in the C1-C4 alkyl group), C1-C4 alkoxy, halogen, nitro, cyano, C1-C4 alkylthio, C1-C4 alkylsulfonyl, amino, mono-C1-C4 alkylamino, or di-C1-C4 alkylamino.

### Claim 9 (depends on 8)

The method of claim 8, wherein each R is C1-C4 alkyl, trifluoromethyl, C1-C4 alkoxy, fluoro, chloro, nitro, or amino.

### Claim 10 (depends on 9)

The method of claim 9, wherein x is 1 and R is at an o-position or an m-position.

### Claim 11 (depends on 2)

The method of claim 2, wherein the compound is applied by spraying a solution or suspension of the compound on the fruit crops.

### Claim 12 (depends on 1)

The method of claim 1, wherein x is 1.

### Claim 13 (depends on 12)

The method of claim 12, wherein R is F.

### Claim 14 (depends on 13)

The method of claim 13, wherein Cy is an unsubstituted diyl of the formula —(CH2CH2)—NR′—(CH2CH2)—, and R′ is an unsubstituted C1-C6 alkyl.

### Claim 15 (depends on 12)

The method of claim 12, wherein R is at an o-position or an m-position.

### Claim 16 (depends on 12)

The method of claim 12, wherein Cy is an unsubstituted C4-C5 alkadiyl or an unsubstituted diyl of the formula —(CH2CH2)—NR′—(CH2CH2)—, where R′ is an unsubstituted C1-C6 alkyl.

### Claim 17 (depends on 1)

The method of claim 1, wherein Cy is —(CH2CH2)—NR′—(CH2CH2)—, where R′ is an unsubstituted C1-C6 alkyl.

### Claim 18 (depends on 17)

The method of claim 17, wherein R′ is —CH3.

### Claim 19 (depends on 1)

The method of claim 1, wherein Cy is an unsubstituted C4-C5 alkadiyl.

### Claim 20 (depends on 19)

The method of claim 19, wherein R is F.