Claims
- 1. A method for controlling algae, comprising applying to the locus of the algae an algicidally effective amount of one or more compounds of the formula: ##STR12## wherein: A is selected from substituted and unsubstituted phenyl, pyridyl, furyl, thienyl, isoxazolyl, oxazolyl, pyrrolyl, isothiazolyl, thiazolyl, pyrazolyl, imidazolyl, pyrimidinyl, quinolyl, isoquinolyl, naphthyl, pyridazinyl, pyrazinyl, benzothienyl, indolyl, benzofuranyl, benzyl, (C.sub.3 -C.sub.7)cycloalkyl, (C.sub.1 -C.sub.6)alkyl, halo(C.sub.1 -C.sub.6)alkyl, (C.sub.2 -C.sub.6)alkenyl, halo(C.sub.2 -C.sub.6)alkenyl, (C.sub.2 -C.sub.6)alkynyl, and halo(C.sub.2 -C.sub.6)alkynyl wherein the substituents are independently selected from:
- a) one to four of halo, cyano, (C.sub.1 -C.sub.6)alkyl, halo(C.sub.1 -C.sub.6)alkyl, (C.sub.2 -C.sub.6)alkenyl, halo(C.sub.2 -C.sub.6)alkenyl, (C.sub.2 -C.sub.6)alkynyl, halo(C.sub.2 -C.sub.6)alkynyl, (C.sub.1 -C.sub.6)alkoxy, halo(C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.6)alkylthio, halo(C.sub.1 -C.sub.6)alkylthio, nitro, --NR.sup.6 R.sup.7, --CR.sup.8 .dbd.NOR.sup.9, NHCOOR.sup.10, --CONR.sup.11 R.sup.12, --COOR.sup.13 ;
- b) fused 5, 6, and 7-membered rings formed from two such substituents; and
- c) fused 5, 6 and 7-membered carbocyclic rings which may contain up to two heteroatoms selected from the group consisting of O, S, N, and P:
- R.sup.1 and R.sup.2 are each independently selected from H, (C.sub.1 -C.sub.6)alkyl, halo(C.sub.1 -C.sub.6)alkyl, (C.sub.2 -C.sub.6)alkenyl, halo(C.sub.2 -C.sub.6)alkenyl, (C.sub.2 -C.sub.6)alkynyl, or halo(C.sub.2 -C.sub.6)alkynyl provided that at least one of R.sup.1 and R.sup.2 is other than H;
- R.sup.6 and R.sup.7 are each independently selected from H, (C.sub.1 -C.sub.6)alkyl, and (C.sub.1 -C.sub.6)alkylcarbonyl;
- R.sup.8 is selected from H, (C.sub.1 -C.sub.6)alkyl, (C.sub.2 -C.sub.6)alkenyl, and (C2-C.sub.6)alkynyl;
- R.sup.9 is selected from H, (C.sub.1 -C.sub.6)alkyl, (C.sub.2 -C.sub.6)alkenyl, (C.sub.2 -C.sub.6)alkynyl, and (C.sub.1 -C.sub.4)alkylcarbonyl;
- R.sup.10, R.sup.11, R.sup.12 and R.sup.13 are each independently selected from H, (C.sub.1 -C.sub.6)alkyl, (C.sub.2 -C.sub.6)alkenyl, and (C.sub.2 -C.sub.6)alkynyl; and
- X, Y and Z are each independently selected from H, halo, cyano, thiocyano, isothiocyano and (C.sub.1 -C.sub.6)alkylsulfonyloxy, provided that at least one of X, Y and Z is halo, cyano, thiocyano, isothiocyano or (C.sub.1 -C.sub.6)alkylsulfonyloxy;
- enantiomers and stereoisomers thereof; and acid addition salts thereof.
- 2. The method of claim 1 wherein the compound has the formula: ##STR13## wherein: R.sup.1 and R.sup.2 are each independently selected from H, (C.sub.1 -C.sub.6)alkyl, halo(C.sub.1 -C.sub.6)alkyl, (C.sub.2 -C.sub.6)alkenyl, and (C.sub.2 -C.sub.6)alkynyl, provided that at least one of R.sup.1 and R.sup.2 is other than H;
- R.sup.3, R.sup.4, and R.sup.5 are each independently selected from:
- a) H, halo, cyano, (C.sub.1 -C.sub.6)alkyl, halo(C.sub.1 -C.sub.6)alkyl, (C.sub.2 -C.sub.6)alkenyl, (C.sub.2 -C.sub.6)alkynyl, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.6)alkylthio, halo(C.sub.1 -C.sub.6)alkoxy, nitro, --NR.sup.6 R.sup.7, --CR.sup.8 .dbd.NOR.sup.9, NHCOOR.sup.10, --CONR.sup.11 R.sup.12, and --COOR.sup.13 ; and
- b) two together form a fused 5, 6 or 7-membered carbocyclic ring which may contain up to two heteroatoms selected from the group consisting of: O, S, N, and P;
- R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11, R.sup.12, and R.sup.13 are each independently selected from H and (C.sub.1 -C.sub.6) alkyl; and
- X and Y are each independently selected from H, halo, cyano, thiocyano, isithiocyano and (C.sub.1 -C.sub.6) alkysulfonyloxy, provided that at least one of X and Y is other than H.
- 3. The method of claim 2 wherein X is chloro; Y is H; R.sup.1 is methyl; R.sup.2 is methyl or ethyl; R.sup.3 and R.sup.5 are each independently selected from the group consisting of H, halo, methyl, nitro, cyano, --NR.sup.6 R.sup.7, --CR.sup.8 .dbd.NOR.sup.9 and --NHCOOR.sup.10 ; R.sup.4 is selected from H, --NR.sup.6 R.sup.7, cyano, --CR.sup.8 .dbd.NOR.sup.9, --NHCOOR.sup.10, COOR.sup.13, and (C.sub.1 -C.sub.4)alkyl; and R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10 and R.sup.13 are each independently H or (C.sub.1 -C.sub.6) alkyl.
- 4. The method of claim 2 wherein R.sup.4 and R.sup.5 together form a fused 5, 6, or 7-membered ring containing up to two heteroatoms selected from the group consisting of O, S, N, and P.
- 5. The method of claim 1 wherein the compound has the formula: ##STR14## wherein R.sup.1 and R.sup.2 are H, (C.sub.1 -C.sub.6)alkyl, halo(C.sub.1 -C.sub.6)alkyl, (C.sub.2 -C.sub.6)alkenyl, and (C.sub.2 -C.sub.6)alkynyl, provided that at least one of R.sup.1 and R.sup.2 is not H;
- R.sup.3 and R.sup.5 are each independently selected from H, halo, cyano, (C.sub.1 -C.sub.6)alkyl, halo(C.sub.1 -C.sub.6)alkyl, (C.sub.2 -C.sub.6)alkenyl, (C.sub.2 -C.sub.6)alkynyl, (C.sub.1 -C.sub.6)alkoxyl, (C.sub.1 -C.sub.6)alkylthio, halo(C.sub.1 -C.sub.6)alkoxyl, nitro, carboxyl, --NR.sup.6 R.sup.7, --CR.sup.8 .dbd.NOR.sup.9, NHCOOR.sup.10, --CONR.sup.11 R.sup.12, and --COOR.sup.13 ;
- R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11, R.sup.12, and R.sup.13 are H or (C.sub.1 -C.sub.6) alkyl; and
- X and Y are each independently selected from H, halo, cyano, thiocyano, isothiocyano and (C.sub.1 -C.sub.6) alkysulfonyloxy, provided that at least one of X and Y is not H.
- 6. The method of claim 1 wherein the compound has the formula: ##STR15## wherein R.sup.1, .sup.2, R.sup.3, R.sup.4, X and Y are as defined in claim 1.
- 7. The method of claim 6 wherein R.sup.3 and R.sup.4 together form a fused 5, 6 or 7 membered carbocyclic ring containing up to two heteroatoms selected from the group consisting of O, S, N, and P.
- 8. The method of claim 1 wherein the compound has the structural formula: ##STR16## wherein: D is O and S;
- R.sup.1 and R.sup.2 are each independently selected from H, (C.sub.1 -C.sub.6)alkyl, halo(C.sub.1 -C.sub.6)alkyl, (C.sub.2 -C.sub.6)alkenyl, and (C.sub.2 -C.sub.6)alkynyl, provided that at least one of R.sup.1 and R.sup.2 is other than H;
- R.sup.3, R.sup.4, and R.sup.5 are each independently selected from:
- a) H, halo, cyano, (C.sub.1 -C.sub.6)alkyl, halo(C.sub.1 -C.sub.6)alkyl, (C.sub.2 -C.sub.6)alkenyl, (C.sub.2 -C.sub.6)alkynyl, (C.sub.1 C.sub.6)alkoxy, (C.sub.1 -C.sub.6)alkylthio, halo(C.sub.1 -C.sub.6)alkoxy, nitro, --NR.sup.6 R.sup.7, --CR.sup.8 .dbd.NOR.sup.9, NHCOOR.sup.10, --CONR.sup.11 R.sup.12, and --COOR.sup.13 ; and
- b) R.sup.4 and R.sup.5 together form a fused 5, 6 or 7-membered carbocyclic ring which may contain up to two heteroatoms selected from the group consisting of: O, S, N, and P:
- R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11, R.sup.12, and R.sup.13 are each independently selected from H and (C.sub.1 -C.sub.6) alkyl; and
- X and Y are each independently selected from H, halo, cyano, thiocyano, isithiocyano and (C.sub.1 -C.sub.6) alkysulfonyloxy, provided that at least one of X and Y is other than H.
- 9. A method to control organisms that cause hard fouling on submerged surfaces, comprising applying to the locus of the organism a compound of the method of claim 1.
- 10. The method of claim 1 wherein the algae are selected from individual species and mixed cultures of green algae, cyanobacteria, and marine algae.
Parent Case Info
This is a nonprovisional application of prior pending provisional application Ser. No. 60/048,010 filed May 29, 1997.
US Referenced Citations (7)
Number |
Name |
Date |
Kind |
3661991 |
McNulty et al. |
May 1972 |
|
4822902 |
Carley et al. |
Apr 1989 |
|
4863940 |
Sharma |
Sep 1989 |
|
5254584 |
Michelotti et al. |
Oct 1993 |
|
5304572 |
Michelotti et al. |
Apr 1994 |
|
5811427 |
Michelotti et al. |
Sep 1998 |
|
5891918 |
Michelotti et al. |
Apr 1999 |
|
Non-Patent Literature Citations (1)
Entry |
S. D. Strauss and P. R. Puckorius, Power, S1, "Cooling-Water Treatment for Control of Scaling, Fouling, Corrosion", Jun. 1984. |