Isothioureido isoindolediones and use as plant growth regulators
AssigneeGulf Oil Corporation
InventorsJoel L. Kirkpatrick, Natu R. Patel, Jerry L. Rutter
Life of this patent
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AssigneeGulf Oil Corporation
InventorsJoel L. Kirkpatrick, Natu R. Patel, Jerry L. Rutter
Estimating the term…
A novel class of compounds which are useful as plant growth regulators is disclosed, having the general structural formula: ##STR1## In which R is C.sub.1 to C.sub.4 alkyl, alkenyl or aklynyl to which may be attached phenyl, pyridyl, benzoyl, phenoxy, halophenoxy, halobenzoyl, N-phenylcarbamyl, N-alkylcarbamyl, N-trifluoromethylthiadiazolylcarbamyl, carboxy, carbalkoxy or halo substituents, R.sup.1 is H, C.sub.1 to C.sub.3 alkyl, alkenyl or alkynyl to which may be attached phenyl, halophenyl or phenoxy groups, acetyl, or R and R.sup.1 together may be C.sub.2 to C.sub.4 alkylene, Ar is phenyl or benzoyl, R.sup.2 is C.sub.1 to C.sub.4 alkyl, alkoxy, alkylene, alkylamino or alkylthio, phenoxy, benzyloxy, carbalkoxy, acetyl, methylenedioxy, trifluoromethyl, nitro, halo or cyano and n may be zero or an integer from 1 to 4, with the provision that at least one position ortho to the point of attachment of a phenyl ring of the Ar structure must be unsubstituted, R.sup.3 is lower alkyl or halo and n' may be zero or an integer from 1 to 4.
A compound which has the structural formula:
2-[1-Methyl-2-allyl-3-(3-fluorophenyl)isothioureido]-1H-isoindole-1,3-(2 H)dione.
2-(1-Methyl-2-propyl-3-phenylisothioureido)-1H-isoindole-1,3-(2H)dione.
2-[1-Methyl-2-(4-bromobenzyl)-3-phenylisothioureido]-1H-isoindole-1,3-(2 H)dione.
2-(1- Methyl-2-pivalylmethyl-3-phenylisothioureido)-1H-isoindole-1,3-(2H)dione.
2-(1,2-Dimethyl-3-phenylisothioureido)-1H-isoindole-1,3-(2H)dione hydroiodide.
2-(1-Methyl-2-allyl-3-phenylisothioureido)-1H-isoindole-1,3-(2H)dione hydrobromide.
2-(1-Methyl-2-benzyl-3-phenylisothioureido)-1H-isoindole-1,3-(2H)dione hydrobromide.
2-(1-Allyl-2-methyl-3-phenylisothioureido)-1H-isoindole-1,3-(2H)dione.
2-(1,2-Diallyl-3-phenylisothioureido)-1H-isoindole-1,3-(2H)dione.
2-[1,2-Dimethyl-3-(3-methylphenyl)isothioureido]-1H-isoindole-1,3 -(2H)dione.
2-[1-Me thyl-2(2-propynyl)-3-(3-fluorophenyl)isothioureido]-1H-isoindole-1,3-(2H)di one hydrobromide.
2-[1,2-Dimeth yl-3-(3-chlorophenyl)isothioureido]-1H-isoindole-1,3-(2H)dione.
2-[1,2-Dimethyl-3-(3,4-dichlorophenyl)isothioureido]-1H-iso indole-1,3-(2H)dione.
2-(1-Methyl-2-allyl-3-phenylisothioureido)-1H-isoindole-1,3-(2H)dione.
2-(1,2-Dimethyl-3-phenylisothioureido)-1H-isoindole-1,3-(2H)dione.
2-(1-Methyl-2-benzyl-3-phenylisothioureido)-1H-isoindole-1,3-(2H)dione.
2-[1,2-Dimethyl-3-(3-fluorophenyl)isothioureido]-1H-isoindole-1,3-(2H)d ione.
2-(1-Methyl-2-ethyl-3-phenylisothioureido)-1H-isoindole-1,3-(2H)dione.
2-[1-Methyl-2-butyl-3-(3,4-dichlorophenyl)isothioureido]-1H-isoindole-1 ,3-(2H)dione.
2-[1-Meth yl-2-methylthiomethyl-3-(3-chlorophenyl)isothioureido]-1H-isoindole-1,3-(2H )dione.
2-( 1,2-Dimethyl-3-phenylisothioureido)-4-methyl-1H-isoindole-1,3-(2H)dione.
2-(1,2-Dimethyl-3-phenylisothioureido)-4-methyl-1H-isoindole-1,3-(2H)di one hydriodide.
2-[1-Methyl -2-carbethoxymethyl-3-(4-fluorophenyl)isothioureido]-1H-isoindole-1,3-(2H)d ione hydrobromide.
2-[1-Methyl-2- carbethoxymethyl-3-(4-fluorophenyl)isothioureido]-1H-isoindole-1,3-(2H)dion e.
2-[1-Methyl-2-carbethoxymethyl-3-(3-fluorophenyl)isothioureido]-1H-isoind ole-1,3-(2H)dione hydrobromide.
2-(2-Ethyl-3-phenylisothioureido)-1H-isoindole-1,3-(2H)dione.
2-(1-Allyl-2-ethyl-3-phenylisothioureido)-1H-isoindole-1,3-(2H)dione.
2-[1,2-Dimethyl-3-(3-trifluoromethylphenyl)isothioureido]-1H-isoindole- 1,3-(2H)dione.
2-[1,2-Dim ethyl-3-(4-chlorophenyl)isothioureido]-1H-isoindole-1,3-(2H)dione.
2-[1-Methyl-2-benzyl-3-(4-chlorophenyl)isothioureido]-1H-isoin dole-1,3-(2H)dione.
2-[1-(2-Propyny l)2-benzyl-3-(4-chlorophenyl)isothioureido]-1H-isoindole-1,3-(2H)dione.
2-[1-Methyl-2-(2,6-dichlorobenzyl)-3-phenylisothioureido]-1H-isoindole- 1,3-(2H)dione.
2-[1-Methy l-2-(4-methylbenzyl)-3-phenylisothioureido]-1H-isoindole-1,3-(2H)dione.
2-(1-Allyl-2-propyl-3-phenylisothioureido)-1H-isoindole-1,3-(2H)dione.
2-(1-Methyl-2-isopropyl-3-phenylisothioureido)-1H-isoindole-1,3-(2H)dio ne.
2-[1,2-Dimethyl-3-(4-methoxyphenyl)isothioureido]-1H-isoindole-1,3-(2H)dio ne.
2-[-2-Ethyl-1-methyl-3-(4-methoxyphenyl)isothioureido]-1H-isoindole-1,3-(2 H)dione.
2-[1 ,2-Dimethyl-3-(2-methylphenyl)isothioureido]-1H-isoindole-1,3-(2H)dione.
2-[2-Ethyl-1-methyl-3-(2-methylphenyl)isothioureido]-1H-isoindole-1,3-( 2H)dione.
2-[1, 2-Dimethyl-3-(2-chlorophenyl)-isothioureido]-1H-isoindole-1,3-(2H)dione.
2-[1,2-Dimethyl-3-(4-fluorophenyl)isothioureido]-1H-isoindole-1,3-(2H)d ione.
2 -[2-Ethyl-1-methyl-3-(2-chlorophenyl)isothioureido]-1H-isoindole-1,3-(2H)di one.
2-[2-Ethyl-1-methyl-3-(4-fluorophenyl)isothioureido]-1H-isoindole-1,3-(2H)d ione.
2 -(1-Allyl-2-isopropyl-3-phenylisothioureido-1H-isoindole-1,3-(2H)dione.
2-(2-Butyl-1-methyl-3-phenylisothioureido)-1H-isoindole-1,3-(2H)dione.
2-(1-Allyl-2-butyl-3-phenylisothioureido)-1H-isoindole-1,3-(2H)dione.
2-(2-Isobutyl-1-methyl-3-phenylisothioureido)-1H-isoindole-1,3-(2H)dion e.
2-[1,2-Dimethyl-3-(4-chloro-3-trifluoromethylphenyl)isothioureido-1H-isoi ndole-1,3-(2H)dione.
2-[1,2-Dimethyl- 3(2-trifluoromethylphenyl)isothioureido]-1H-isoindole-1,3-(2H)dione.
2-{2-[2-(2,4-Dichlorophenoxy)ethyl]-1-methyl-3-phenylisothiourei do}-1H-isoindole-1,3-(2H)dione.
2-[1,2-Dimethyl-3-(3-methox yphenyl)isothioureido]-1H-isoindole-1,3-(2H)dione.
2-[1,2-Dimethyl-3-(3-methylthiophenyl)isothiou reido]-1H-isoindole-1,3-(2H)dione.
2-[1,2-Dimethyl-3-(4-chloro-2- methylphenyl)isothioureido]-1H-isoindole-1,3-(2H)dione.
2-[1,2-Dimethyl-3-(2,4-dichlorophenyl)isothioureido ]-1H-isoindole-1,3-(2H)dione.
2-[1,2-Dimethyl-3-(4-etho xyphenyl)isothioureido]-1H-isoindole-1,3-(2H)dione.
2-[1,2-Dimethyl-3-(2-fluorophenyl)isothioureido ]-1H-isoindole-1,3-(2H)dione.
2-[2-Ethyl-1-methyl-3-(2, 4-dichlorophenyl)isothioureido]-1H-isoindole-1,3-(2H)dione.
2-[2-Ethyl-1-methyl-3-(4-ethoxyphenyl)isothioureido]-1H -isoindole-1,3-(2H)dione.
2-[2-Allyl-1-methyl-3 -(4-trifluoromethylphenyl)isothioureido]-1H-isoindole-1,3-(2H)dione.
2-{2-[2-(2,4-Dichlorophenoxy)ethyl]-1-methyl-3-(2-fluorophenyl)i sothioureido}-1H-isoindole-1,3-(2H)dione.
2-[2-(1-Benzoyl)ethyl-1-methyl-3-(4-m ethoxyphenyl)-isothioureido]-1H-isoindole-1,3-(2H)dione.
2-[2-(4-Fluorobenzoylmethyl)-1-methyl-3-(2-methylphe nyl)isothioureido]-1H-isoindole-1,3-(2H)dione.
2-[2-(4-Fluorobenzoylmethyl)-1-methyl-3-(2 -fluorophenyl)isothioureido]-1H-isoindole-1,3-(2H)dione.
2-(2-Carboxymethyl-1-methyl-3-phenylisothioureido)-1 H-isoindole-1,3-(2H)dione hydrobromide.
2-[1-(3-Chlorobenzyl)-2-methyl-3-ph enylisothioureido]-1H-isoindole-1,3-(2H)dione.
2-[2-(3-Phenyl-2-propenyl)-3-(3-fluorophen yl)-isothioureido]-1H-isoindole-1,3-(2H)dione.
2{2-[2-(N-Ethyl-N-phenylcarbamyl)ethyl]-1- methyl-3-(3-fluorophenyl)isothioureido}-1H-isoindole-1,3-(2H)dione.
2-[1-Methyl-2-(3,4,4-trifluoro-3-butenyl)-3-(3-fluorophenyl)iso thioureido]-1H-isoindole-1,3-(2H)dione.
2-[1-Methyl-2-(3,4,4-trifluoro-3-bu tenyl)-3-phenylisothioureido-1H-isoindole-1,3-(2H)dione.
2-[1,2-Dimethyl-3-(3-methylbenzoyl)isothioureido]-1H -isoindole-1,3-(2H)dione.
Dependencies are inferred from the claim text.