Claims
- 1. A dihydropyridazinone and pyridazinone compound having the structure ##STR21## wherein W is ##STR22## n is 0 or 1; Y is O, S, NR.sub.1, or R.sub.6 ;
- the ring bond containing R.sub.4 and R.sub.5 is a single or double bond;
- X is independently selected from hydrogen, halo, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy and --HC.dbd.CH--CH.dbd.CH-- thereby forming a naphthyl ring;
- R is independently selected from (C.sub.1 -C.sub.12)alkyl and halo(C.sub.1 -C.sub.12)alkyl;
- R.sub.1 is independently selected from (C.sub.1 -C.sub.12)alkyl, (C.sub.2 -C.sub.8)alkenyl, phenyl and naphthyl which phenyl or naphthyl may be substituted with up to three substituents selected from the group consisting of halogen, cyano, nitro, trihalomethyl, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkylthio, (C.sub.1 -C.sub.4)alkylsulfoxide (C.sub.1 -C.sub.6)alkoxy and halo(C.sub.1 -C.sub.4)alkyl, excluding phenyl or naphthyl substituted with 2-alkylthio, 2-alkylsulfoxide, or adjacent trinitro, triiodo or tri-tertbutyl moieties;
- R.sub.2 is independently selected from hydrogen, (C.sub.1 -C.sub.12)alkyl, (C.sub.1 -C.sub.12)alkoxy, halo(C.sub.1 -C.sub.12)alkyl, halo(C.sub.1 -C.sub.12)alkoxy, hydroxy(C.sub.1 -C.sub.12)alkyl, (C.sub.1 -C.sub.12)alkoxy(C.sub.1 -C.sub.12)alkyl, (C.sub.1 -C.sub.12)alkoxycarbonyl(C.sub.1 -C.sub.12)alkyl, (C.sub.2 -C.sub.8)alkenyl, halo(C.sub.2 -C.sub.8)alkenyl, (C.sub.3 -C.sub.10)alkynyl, halo(C.sub.3 -C.sub.10)alkynyl, (C.sub.3 -C.sub.7)cycloalkyl, (C.sub.3 -C.sub.7)cycloalkyl(C.sub.1 -C.sub.4)alkyl, PO(OR.sub.1).sub.2 (C.sub.1 -C.sub.12)alkyl, R.sub.1 S(O).sub.2 (C.sub.1 -C.sub.12)alkyl, (R.sub.1).sub.3 Si(C.sub.1 -C.sub.12)alkyl, phenoxy(C.sub.1 -C.sub.12)alkyl, naphthyloxy(C.sub.1 -C.sub.12)alkyl, phenylcarbonyl(C.sub.1 -C.sub.12)alkyl, naphthylcarbonyl(C.sub.1 -C.sub.12)alkyl, phenylalkyl, naphthylalkyl, phenylalkenyl, naphthylalkenyl, phenyl, and naphthyl, any of which phenyl or naphthyl may be substituted with up to three substituents selected from the group consisting of halogen, cyano, nitro, trihalomethyl, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkylthio, (C.sub.1 -C.sub.4)alkylsulfoxide (C.sub.1 -C.sub.6)alkoxy and halo(C.sub.1 -C.sub.4)alkyl, excluding phenyl or naphthyl substituted with 2-alkylthio, 2-alkylsulfoxide, or adjacent trinitro, trilodo or tritertbutyl moieties;
- R.sub.4 and R.sub.5 are independently selected from hydrogen, halo, (C.sub.1 -C.sub.8)alkyl, (C.sub.1 -C.sub.8)alkoxy, cyano, halo(C.sub.1 -C.sub.12)alkyl, (C.sub.2 -C.sub.8)alkenyl, (C.sub.3 -C.sub.10)alkynyl, aryl and aralkyl; and
- R.sub.6 is (C.sub.1 -C.sub.12) alkyl and (C.sub.2 -C.sub.12) alkenyl.
- 2. The compound of claim 1 wherein the ring bond between the carbon bonded to R.sub.4 and R.sub.5 is a double bond.
- 3. The compound of claim 1 wherein the ring bond between the carbon bonded to R.sub.4 and R.sub.5 is a single bond.
- 4. The compounds of claim 2 wherein R.sub.4 and R.sub.5 are hydrogen, the moiety ##STR23## is meta to Y, R is methyl and R.sub.2 is selected from the group consisting of (C.sub.1 -C.sub.12)alkyl, (C.sub.2 -C.sub.8)alkenyl, halo(C.sub.1 -C.sub.12)alkyl, phenylalkyl, naphthylalkyl wherein the phenyl and naphthyl rings can be optionally substituted, and halo(C.sub.2 -C.sub.8)alkenyl.
- 5. The compound of claim 4 wherein n=0, X is hydrogen and R.sub.2 is selected from the group consisting of ethyl, propyl, butyl, vinyl, allyl, chloroethyl, fluoroethyl and substituted benzyl.
- 6. The compound of claim 5 wherein R.sub.2 is selected from halosubstituted benzyl, (C.sub.1-C.sub.4)alkyl substituted benzyl, trihalosubstituted benzyl and cyano substituted benzyl.
- 7. The compound of claim 6 wherein R.sub.2 is selected from 2-chlorobenzyl, 3-chlorobenzyl, 4-chlorobenzyl, 2-fluorobenzyl, 3-fluorobenzyl, 4-fluorobenzyl, 2-cyanobenzyl, 3-cyanobenzyl, 4-cyanobenzyl and 4-trifluoromethylbenzyl.
- 8. The compounds of claim 3 wherein R.sub.4 and R.sub.5 are hydrogen, the moiety ##STR24## is meta to Y, R is methyl and R.sub.2 is selected from the group consisting of (C.sub.1 -C.sub.12)alkyl, (C.sub.2 -C.sub.8)alkenyl, halo(C.sub.1 -C.sub.12)alkyl, phenylalkyl, naphthylalkyl wherein the phenyl and naphthyl rings can be optionally substituted, and halo(C.sub.2 -C.sub.8)alkenyl.
- 9. The compound of claim 8 wherein n=0, X is hydrogen and R.sub.2 is selected from the group consisting of ethyl, propyl, butyl, vinyl, allyl, chloroethyl, fluoroethyl and substituted benzyl.
- 10. The compound of claim 9 wherein R.sub.2 is selected from halosubstituted benzyl, (C.sub.1 -C.sub.4)alkyl substituted benzyl, trihalosubstituted benzyl and cyano substituted benzyl.
- 11. The compound of claim 10 wherein R.sub.2 is selected from 2-chlorobenzyl, 3-chlorobenzyl, 4-chlorobenzyl, 2-fluorobenzyl, 3-fluorobenzyl, 4-fluorobenzyl, 2-cyanobenzyl, 3-cyanobenzyl, 4-cyanobenzyl and 4-trifluoromethylbenzyl.
- 12. A fungicidal composition for controlling phytopathogenic fungi which comprises an agronomically acceptable carrier and the compound of claim 1 wherein the ratio of the carrier to the compound is 99:1 to 1:4.
- 13. The composition of claim 12 wherein the ratio of the agriculturally acceptable carrier to compound is 10:1 to 1:3.
- 14. A method for controlling phytopathogenic fungi which comprises applying to the locus where control is desired the compound of claim 1 at a rate of from 0.005 to 50 kilograms per hectare.
- 15. The method of claim 14 wherein the compound of claim 1 is applied at the rate of from 0.025 to 10 kilograms per hectare.
- 16. A method for controlling insects which comprises applying to the insect's habitat the compound of claim 1 at a rate of 0.005 to 10 kilograms per hectare.
- 17. The method of claim 16 wherein the compound is applied at a rate of 0.01 to 1 kilogram per hectare.
Parent Case Info
This application claims the benefit of prior U.S. Provisional Application No. 60/028,336 filed Oct. 11, 1996.
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