# US 11,026,426 B2 · Oxadiazole and phenol derivatives as antibacterial and/or herbicidal agents

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- Number: US 11,026,426 B2
- Document ID: US11026426B2
- Status: Granted
- Kind: B2
- Application number: 15/933,608
- Filed: 2018-03-23
- Published: 2018-09-27
- Granted: 2021-06-08
- Earliest claimed: 2017-03-24
- Assignees: Northern Illinois Research Foundation
- Applicants: Northern Illinois Research Foundation
- Inventors: Timothy J. Hagen; Michael Thompson; Jeremy R. Troxell; Brian E. Hartnett
- Web page: https://patentgrep.com/patent/US11026426B2

## CPC

- A01N 43/82: five-membered rings with three ring hetero atoms
- A01N 43/36: five-membered rings
- A61K 31/4245: Oxadiazoles
- C07D 209/12: Radicals substituted by oxygen atoms
- C07D 413/04: directly linked by a ring-member-to-ring-member bond
- C07D 417/04: directly linked by a ring-member-to-ring-member bond
- 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
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Compounds of formula I and II are described. In formulae I and II, X is —NH— or —S— and Y is —CH═ or —N═. In formula I, Z is C1-C6 alkylene, C2-C6 alkenylene, C6-C10 arylene, or C3-C6 cycloalkylene, or Z is absent. In formula I, R is hydrogen, halogen, —OH, —NO2, C1-C6 alkyl, C2-C6 alkenyl, C6-C10aryl, —O(C1-C6 alkyl), or —O(C6-C10 aryl), wherein each hydrogen atom in C1-C6 alkyl, C2-C6 alkenyl, C6-C10 aryl, —O(C1-C6 alkyl), and —O(C6-C10 aryl) is independently optionally substituted by halogen, —OH, or —NO2. In formula II, R1, R2, R3, and R4 are each independently hydrogen, halogen, —OH, —NO2, C1-C6 alkyl, C2-C6 alkenyl, or C6-C10 aryl, wherein each hydrogen atom in C1-C6 alkyl, C2-C6 alkenyl, and C6-C10 aryl is independently optionally substituted by halogen, —OH, or —NO2. Methods of inhibiting bacteria are also described.

## Claims

### Claim 1

A method to inhibit bacteria, the method comprising contacting the bacteria with a compound of the formula I
wherein
X is NH or S;
Y is CH or N;
Z is selected from the group consisting of C1-C6 alkylene, C2-C6 alkenylene, and C3-C6 cycloalkylene, or Z is absent; and
R is selected from the group consisting of halogen, —OH, —NO2, C2-C6 alkenyl, —O(C1-C6 alkyl), and —O(C6-C10 aryl), wherein each hydrogen atom in C2-C6 alkenyl, and —O(C1-C6 alkyl) is independently optionally substituted by halogen, —OH, or —NO2, and wherein each hydrogen atom in —O(C6-C10 aryl) is optionally substituted by —OH.