Title: Method of regulating the growth of aquatic weeds with pyridine derivatives

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1. A method for inhibiting the growth of submerged and floating aquatic weeds which comprises adding to the water containing said weeds an amount sufficient to provide a growth-regulating and non-herbicidal concentration of a compound of the formula ##STR2## wherein X is hydrogen, hydroxyl, halo, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.6 alkylthio, cyclohexylthio, 4-chlorophenylthio, --N(R.sup.3).sub.2, acetamido, imidazol-l-yl, morpholino, or cyano;

R.sup.1 is hydrogen, C.sub.1 -C.sub.9 alkyl, ethynyl, C.sub.3 -C.sub.6 cycloalkyl, benzyl, phenyl, or monohalophenyl;

R.sup.2 is C.sub.1 -C.sub.9 alkyl, C.sub.3 -C.sub.6 cycloalkyl, cyclohexylmethyl, cyclohexylethyl, phenyl, monohalophenyl, dihalophenyl, 3,4-(methylenedioxy)phenyl, trifluoromethylphenyl, p-cumenyl, tolyl, phenoxyphenyl, phenoxy(C.sub.1 -C.sub.4)alkyl, benzyl, C.sub.1 -C.sub.4 alkoxyphenyl, pentafluorophenyl, xylyl, 2-thienyl, 3-pyridyl, 1,3-dioxan-5-yl, or 5-methyl-1,3-dioxan-5-yl; and

R.sup.1 and R.sup.2, when taken together with the carbon atom to which they are attached, form 2,6-dimethylcyclohexan-1-yl, 9-fluorenyl, 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl, 9-xanthenyl, 5H-dibenzo[a,d]cyclohepten-5-yl, or 9-thioxanthenyl;

R.sup.3 is hydrogen or C.sub.1 -C.sub.6 alkyl; and

the nonphytotoxic acid addition salts thereof.

2. The method of claim 1 wherein the growth-regulating and non-herbicidal concentration of the active compound ranges from about 0.25 to about 10 ppm.

3. The method of claim 1 wherein the active compound is of the formula ##STR3## wherein X is hydrogen, hydroxyl or methoxy;

R.sup.1 is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.6 cycloalkyl, or phenyl;

R.sup.2 is C.sub.1 -C.sub.8 alkyl, cyclohexylmethyl, cyclohexyl, phenyl, 4-fluorophenyl, 4-chlorophenyl, 4-methoxyphenyl, p-tolyl, or 4-phenoxy-n-butyl;

R.sup.1 and R.sup.2, when taken together with the carbon atom to which they are attached, form 9-fluorenyl, 9-xanthenyl, or 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl; and

the nonphytotoxic acid addition salts thereof.

4. The method of claim 1 wherein the active compound is of the formula ##STR4## wherein X is hydrogen, hydroxyl or methoxy;

R.sup.1 is C.sub.3 -C.sub.8 alkyl, cyclopropyl, cyclohexyl, or phenyl;

R.sup.2 is C.sub.4 -C.sub.7 alkyl, 4-chlorophenyl, 4-fluorophenyl, 4-methoxyphenyl, p-tolyl, cyclohexylmethyl, phenyl, and 4-phenoxy-n-butyl;

R.sup.1 and R.sup.2, when taken together with the carbon to which they are attached, form 9-fluorenyl; and

the nonphytotoxic acid addition salts thereof.

5. The method of claim 1 wherein the active compound is of the formula ##STR5## wherein X is hydroxyl;

R.sup.1 is isopropyl, cyclopropyl, isobutyl, t-butyl, or phenyl;

R.sup.2 is n-hexyl, phenyl, 4-fluorophenyl, 4-methoxyphenyl, or 4-chlorophenyl; and

the nonphytotoxic acid addition salts thereof.

6. The method of claim 1 wherein the active compound is .alpha.,.alpha.-diphenyl-3-pyridinemethanol.

7. The method of claim 1 wherein the active compound is .alpha.-(4-chlorophenyl)-.alpha.-cyclopropyl-3-pyridinemethanol hydrochloride.

8. The method of claim 1 wherein the active compound is .alpha.,.alpha.-diisobutyl-3-pyridinemethanol.

9. The method of claim 1 wherein the active compound is .alpha.-hexyl-.alpha.-isobutyl-3-pyridinemethanol.

10. The method of claim 1 wherein the active compound is .alpha.-(4-chlorophenyl)-.alpha.-isopropyl-3-pyridinemethanol.

11. The method of claim 1 wherein the active compound is 3-pyridyl diphenylmethane.

12. The method of claim 1 wherein the active compound is .alpha.-isopropyl-.alpha.-(4-methoxyphenyl)-3-pyridinemethanol.

13. The method of claim 1 wherein the active compound is .alpha.-(t-butyl)-.alpha.-(4-fluorophenyl)-3-pyridinemethanol.
Other info:

Inventors: Krumkalns, Eriks V. (Indianapolis, IN, US)

Application Number: 833541
Filing Date: 1977-09-15
Publication_date: 1978-09-26
Assignee: Eli Lilly and Company (Indianapolis, IN)
Primary Class(es): 504/155 504/156
Other Classes:
US Patent Ref:

3244722	Apr, 1966	Johnson	71/66.
3655359	Apr, 1972	Krumkalns et al.	71/94.
3746531	Jul, 1973	Doherty	71/66.

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