Title: Method of controlling aquatic weeds

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1. A method of destroying aquatic weeds in water which comprises contacting the weeds with an herbicidally-effective amount of a compound of the formula ##STR11## wherein A is hydrogen, bromo, or chloro;

B is cyclohexyl, benzyl, or phenyl;

X is oxygen or sulfur;

m is 0 or 1;

when m = 0, n + p is 2 through 10; and

when m = 1, n = p = 1, or n = 2, p = 0;

R.sup.1, when taken alone, is hydrogen, C.sub.1 -C.sub.5 alkyl, or --CH.sub.2 CH.sub.2 OH;

R.sup.2, when taken alone, is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.3 alkenyl, cyclohexyl, --CH.sub.2 CH.sub.2 OH, --(CH.sub.2).sub.3 OCH.sub.3, 1-adamantyl, or phenyl;

R.sup.1 and R.sup.2, when taken together with the nitrogen atom to which they are attached, form morpholino, 2-methylpiperidino, 4-(2-hydroxyethyl)piperazino, or pyrrolidino; and

the acid addition salts thereof.

2. The method of claim 1 wherein the active compound is of the formula ##STR12## A is chloro; B is phenyl;

m is 0 or 1;

when m = 0, n + p is 2 through 6; and

when m = 1, n = p 32 1, or n = 2, and p = 0;

R.sup.1 is hydrogen, C.sub.1 -C.sub.5 alkyl, or -CH.sub.2 CH.sub.2 OH;

R.sup.2 is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.3 alkenyl, --CH.sub.2 CH.sub.2 OH, --(CH.sub.2).sub.3 OCH.sub.3, or cyclohexyl; and

the acid addition salts thereof.

3. The method of claim 1 wherein the active compound is of the formula ##STR13## wherein m is 0 or 1;

when m = 0, n + p is 2, 3, or 4;

when m = 1, n = 2, and p = 0;

R.sup.2 is C.sub.2 -C.sub.4 alkyl, cyclohexyl, or --(CH.sub.2).sub.3 OCH.sub.3 ; and the acid addition salts thereof.

4. The method of claim 1 wherein the herbicidally-effective amount of the active compound is from about 0.5 to about 10 ppm.

5. The method of claim 1 wherein the active compound is 3-(5-chloro-2-biphenylyloxy)-N-ethyl-1-methylpropylamine hydrochloride.

6. The method of claim 1 wherein the active compound is N-(t-butyl)-3-(5-chloro-2-biphenylyloxy)propylamine hydrochloride.

7. The method of claim 1 wherein the active compound is 3-(5-chloro-2-biphenylyloxy)-N-isopropylpropylamine hydrochloride.

8. The method of claim 1 wherein the active compound is 3-(5-chloro-2-biphenylyloxy)-N-ethyl-N-(2-hydroxyethyl)propylamine hydrochloride.

9. The method of claim 1 wherein the active compound is 4-(5-chloro-2-biphenylyloxy)-N-cyclohexylbutylamine hydrochloride.
Other info:

Inventors: Lacefield, William B. (Indianapolis, IN, US)

Application Number: 783124
Filing Date: 1977-03-31
Publication_date: 1978-02-21
Assignee: Eli Lilly and Company (Indianapolis, IN)
Primary Class(es): 504/160 504/155, 504/156
Other Classes:
US Patent Ref:

2723193	Nov, 1955	Todd	71/66.
3677735	Jul, 1972	Richter et al.	71/66.
3808257	Apr, 1974	Richter et al.	71/66.

Other Refs:
Primary Examiner: Gotts, Lewis
Assistant Examiner: Mills, Catharine L.
Attorney: Morrison; Dwight E., Whale; Arthur R.