Substituted aminoquinazolinone (thione) derivatives or salts...

Details Substituted aminoquinazolinone (thione) derivatives or salts... Substituted aminoquinazolinone (thione) derivatives or salts...

2000-11-01

2002-09-24

Rao, Deepak R. (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C544S284000

Reexamination Certificate

active

06455535

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to substituted aminoquinazolinone (thione) derivatives or salts thereof, intermediates thereof for preparing the same, pest controllers and a method for using the same.
2. Related Art
Japanese Patent Unexamined Publication, JP-A-8-325239 discloses that aminoquinazolinone derivatives are useful as pest controllers.
SUMMARY OF THE INVENTION
As a consequence of investigation earnestly conducted for finding a novel pest controller, the present inventors found that compounds of the present invention, having the substituents in the phenyl group which is belonging to the quinazolinone ring, possess the same or better insecticidal effects at low dosage as compared with compounds of Examples disclosed in the above-mentioned JP-A-8-325239. Particularly the compounds of the present invention possess sufficient insecticidal effects against whiteflies under consideration in the agricultural and horticultural fields, consequently the present inventors have accomplished the present invention.
The substituted aminoquinazolinone (thione) derivatives or salts thereof represented by the general formula (I) and the compounds represented by the general formula (II) which are intermediates for preparing the derivatives of the general formula (I) are novel compounds which have not been known in any prior art literature. Furthermore, pest controllers containing, as the active ingredient, the substituted aminoquinazolinone (thione) derivative represented by the general formula (I) or salts thereof possess excellent insecticidal effects against various insects at low dosage as compared with conventional pest controllers.
The present inventors have earnestly conducted investigation on the aminoquinazolinone (thione) derivatives for developing a novel pest controller having expanded insceticidal spectrum. Finally, the inventors have found the fact that novel aminoquinazolinone derivatives having bromine atom, iodine atom, perfluoroalkyl group, perfluoroalkoxy group or the like in the quinazoline ring possess quite excellent insecticidal activities as pest controllers.
DETAILED DESCRIPTION OF THE INVENTION
The present invention relates to substituted aminoquinazolinone (thione) derivatives represented by the general formula (I), or salts thereof:
[where R is a hydrogen atom; a hydroxyl group; a formyl group; a (C
1-12
)alkyl group; a halo(C
1-6
)alkyl group; a hydroxy(C
1-6
)alkyl group; a (C
2-6
)alkenyl group; a (C
2-6
)-alkynyl group; a (C
1-6
)alkoxy group; a halo(C
1-6
)alkoxy group; a (C
1-6
)alkoxy(C
1-3
)alkyl group; a (C
1-6
)alkoxy(C
1-3
)alkoxy(C
1-3
)alkyl group; a (C
1-6
)alkylthio group; a halo(C
1-6
)alkylthio group; a (C
1-6
)alkylsulfinyl group; a (C
1-6
)alkylsulfonyl group; a (C
1-6
)alkylthio(C
1-3
)alkyl group; a di(C
1-6
)alkoxy(C
1-3
)alkyl group in which the (C
1-6
)alkoxy groups may be the same or different; an unsubstituted amino(C
1-6
)alkyl group; a substituted amino(C
1-6
)alkyl group having one or two substituents which may be the same or different and are selected from the group consisting of (C
1-6
)alkyl groups, halo(C
1-6
)alkyl groups, (C
2-6
)alkenyl groups and (C
2-6
)alkynyl groups; a cyano(C
1-6
)alkyl group; a (C
1-6
)alkylcarbonyl group; a (C
1-6
)alkoxycarbonyl group; a hydroxycarbonyl-(C
1-3
)alkyl group; a (C
1-6
)alkoxycarbonyl(C
1-3
)alkyl group; an unsubstituted aminocarbonyl group; a substituted aminocarbonyl group having one or two substituents which may be the same or different and are selected from the group consisting of (C
1-6
)alkyl groups, (C
2-6
)alkenyl groups and (C
2-6
)alkynyl groups; a (C
3-6
)-cycloalkyl(C
1-3
)alkyl group; an unsubstituted phenyl(C
1-3
)alkyl group; a substituted phenyl(C
1-3
)alkyl group having on the ring 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro groups, cyano groups, (C
1-6
)alkyl groups, halo(C
1-6
)alkyl groups, (C
1-6
)alkoxy groups, halo(C
1-6
)alkoxy groups, (C
1-6
)alkylthio groups and halo(C
1-6
)alkylthio groups; an unsubstituted phenylcarbonyl group; a substituted phenylcarbonyl group having on the ring 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro groups, cyano groups, (C
1-6
)alkyl groups, halo(C
1-6
)alkyl groups, (C
1-6
)alkoxy groups, halo(C
1-6
)alkoxy groups, (C
1-6
)alkylthio groups and halo(C
1-6
)alkylthio groups; an unsubstituted phenylthio group; a substituted phenylthio group having on the ring 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro groups, cyano groups, (C
1-6
)alkyl groups, halo(C
1-6
)alkyl groups, (C
1-6
)alkoxy groups, halo(C
1-6
)alkoxy groups, (C
1-6
)alkylthio groups and halo(C
1-6
)alkylthio groups; an unsubstituted phenyl-sulfonyl group; a substituted phenylsulfonyl group having on the ring 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro groups, cyano groups, (C
1-6
)alkyl groups, halo(C
1-6
)alkyl groups, (C
1-6
)alkoxy groups, halo(C
1-6
)alkoxy groups, (C
1-6
)alkylthio groups and halo(C
1-6
)alkylthio groups; an unsubstituted phenyl(C
1-6
)alkylsulfonyl group; a substituted phenyl(C
1-6
)alkylsulfonyl group having on the ring 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro groups, cyano groups, (C
1-6
)alkyl groups, halo(C
1-6
)alkyl groups, (C
1-6
)alkoxy groups, halo(C
1-6
)alkoxy groups, (C
1-6
)alkylthio groups and halo(C
1-6
)alkylthio groups; an unsubstituted phenyloxycarbonyl group; a substituted phenyloxycarbonyl group having on the ring 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro groups, cyano groups, (C
1-6
)alkyl groups, halo(C
1-6
)alkyl groups, (C
1-6
)alkoxy groups, halo(C
1-6
)-alkoxy groups, (C
1-6
)alkylthio groups and halo(C
1-6
)-alkylthio groups; an unsubstituted phenyloxy(C
1-3
)alkyl group, a substituted phenyloxy(C
1-3
)alkyl group having on the ring 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro groups, cyano groups, (C
1-6
)alkyl groups, halo(C
1-6
)alkyl groups, (C
1-6
)alkoxy groups, halo(C
1-6
)alkoxy groups, (C
1-6
)alkylthio groups and halo(C
1-6
)alkylthio groups; an unsubstituted phenyl(C
2-6
)-alkenyl group, a substituted phenyl(C
2-6
)alkenyl group having on the ring 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro groups, cyano groups, (C
1-6
)alkyl groups, halo(C
1-6
)alkyl groups, (C
1-6
)alkoxy groups, halo(C
1-6
)alkoxy groups, (C
1-6
)alkylthio groups, halo(C
1-6
)alkylthio groups and (C
1-2
)alkylenedioxy groups; an unsubstituted phenyl(C
2-6
)alkynyl group; a substituted phenyl(C
2-6
)alkynyl group having on the ring 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro groups, cyano groups, (C
1-6
)alkyl groups, halo(C
1-6
)alkyl groups, (C
1-6
)alkoxy groups, halo(C
1-6
)alkoxy groups, (C
1-6
)alkylthio groups, halo(C
1-6
)alkylthio groups and (C
1-2
)alkylenedioxy groups; an unsubstituted phenyl(C
2-4
)alkynyl(C
1-3
)alkyl group; a substituted phenyl(C
2-4
)alkynyl(C
1-3
)alkyl group having on the ring 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro groups, cyano groups, (C
1-6
)alkyl groups, halo(C
1-6
)alkyl groups, (C
1-6
)alkoxy groups, halo(C
1-6
)alkoxy groups, (C
1-6
)alkylthio groups, halo(C
1-6
)alkylthio groups and (C
1-2
)alkylenedioxy groups; a 1,3-dioxolan-2-yl(C
1-3
)alkyl group; or a phthalimido(C
1-6
)alkyl group,
R
1
is a 5- or 6-membered heterocyclic ring having 1 to 3 heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitroge

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