Tetrahydrophtalimides, and their production and use

Claim 2

A compound of the formula: wherein R 1 is a hydrogen atom, a C 1 ―C 5 alkyl group, a C 3 -C 4 alkenyl group, a C 3 ―C 4 alkynyl group, a C 1 ―C 4 haloalkyl group, a C 3 ―C 4 haloalkenyl group, a C 3 -C 4 haloalkynyl group, a C 1 -C 2 alkoxy(C 1 ―C 2 )alkyl group or a C 1 ―C 2 alkoxy(C 1 ―C 2 )-alkoxy(C 1 ―C 2 )alkyl group, R 2 and R 3 are the same or different and each a hydrogen atom, a halogen atom, a C 1 -C 3 alkyl group or a phenyl group, X is a hydrogen atom, a chlorine atom or a fluorine atom and n is an integer of 0 or 1.

Claim 3

The compound according to claim 1, wherein X is a hydrogen atom or a fluorine atom.

Claim 4

The compound according to claim 2, wherein R 1 is a C 1 -C 4 alkyl group, a C 3 -C 4 alkenyl group, a C 3 ―C 4 alkynyl group, a C 3 ―C 4 haloalkynyl group or a C 1 -C 2 alkoxymethyl group and either one of R 2 and R 3 is a hydrogen atom, a methyl group or an ethyl group.

Claim 5

The compound according to claim 3, wherein R 1 is a C 1 -C 3 alkyl group, a C 3 -C 4 alkenyl group, a C 3 ―C 4 alkynyl group or a halopropynyl group.

Claim 6

The compound according to claim 4, wherein n is an integer of 1.

Claim 7

The compound according to claim 5, wherein R 2 is a hydrogen atom or a methyl group and R 3 is a hydrogen atom.

Claim 8

The compound according to claim 6, wherein R 1 is a C 3 -C 4 alkynyl group or a C 3 -C 4 alkenyl group.

Claim 9

The compound according to claim 1, which is 2-[4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-on-6-yl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione.

Claim 10

The compound according to claim 1, which is 2-[2-methyl-4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-on-6-yl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione.

Claim 11

The compound according to claim 1, which is 2-[7-fluoro-4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-on-6-yl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione.

Claim 12

The compound according to claim 1, which is 2-[7-fluoro-2-methyl-4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-on-6-yl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione.

Claim 13

A compound of the formula: wherein R 1 is a hydrogen atom, a C 1 ―C 5 alkyl group, a C 3 ―C 4 alkenyl group, a C 3 ―C 4 alkynyl group, a C 1 ―C 4 haloalkyl group, a C 3 ―C 4 haloalkenyl group, a C 3 ―C 4 haloalkynyl group, a C 1 -C 2 alkoxy(C 1 -C 2 )alkyl group or a C 1 ―C 2 , alkoxy(C 1 ―C 2 )-alkoxy(C 1 ―C 2 )alkyl group, R 2 and R 3 are the same or different and each a hydrogen atom, a halogen atom, a C 1 -C 3 alkyl group or a phenyl group, X is a hydrogen atom, a chlorine atom or a fluorine atom, n is an integer of 0 or 1 and A is an amino group or a nitro group.

Claim 14

A compound of the formula: wherein R 1 is a hydrogen atom, a C 1 ―C 5 alkyl group, a C 3 ―C 4 alkenyl group, a C 3 ―C 4 alkynyl group, a C 1 ―C 4 haloalkyl group, a C 3 ―C 4 haloalkenyl group, a C 3 ―C 4 haloalkynyl group, a C 1 -C 2 alkoxy(C 1 -C 2 )alkyl group or a C 1 ―C 2 , alkoxy(C 1 ―C 2 )-alkoxy(C 1 ―C 2 )alkyl group, R 2 and R 3 are the same or different and each a hydrogen atom, a halogen atom, a C 1 -C 3 alkyl group or a phenyl group, X is a hydrogen atom, a chlorine atom or a fluorine atom, n is an integer of 0 or 1 and A is an amino group or a nitro group.

Claim 15

A compound of the formula: wherein R 1 is a hydrogen atom, a C 1 ―C 5 alkyl group, a C 3 ―C 4 alkenyl group, a C 3 -C 4 alkynyl group, a C 1 -C 4 haloalkyl group, a C 3 ―C 4 haloalkenyl group, a C 3 ―C 4 haloalkynyl group, a C 1 -C 2 alkoxy(C 1 ―C 2 )alkyl group or a C 1 -C 2 alkoxy(C 1 ―C 2 )-alkoxy(C 1 ―C 2 )alkyl group, R 2 and R 3 are the same or different and each a hydrogen atom, a halogen atom, a C 1 -C 3 alkyl group or a phenyl group.

Claim 16

A compound of the formula: wherein R 1 is a hydrogen atom, a C 1 ―C 5 alkyl group, a C 3 ―C 4 alkenyl group, a C 3 -C 4 alkynyl group, a C 1 -C 4 haloalkyl group, a C 3 ―C 4 haloalkenyl group, a C 3 ―C 4 haloalkynyl group, a C 1 -C 2 alkoxy(C 1 ―C 2 )alkyl group or a C 1 -C 2 alkoxy(C 1 ―C 2 )-alkoxy(C 1 ―C 2 )alkyl group, R 2 and R 3 are the same or different and each a hydrogen atom, a halogen atom, a C 1 -C 3 alkyl group or a phenyl group.

Claim 17

A process for preparing the compound according to claim 1, which comprises reacting an amino compound of the formula: wherein R 1 , R 2 , R 3 , X and n are each as defined in claim 1, with 3,4,5,6-tetrahydrophthalic anhydride in a solvent.

Claim 18

A composition which comprises as an active ingredient a herbicidally effective amount of the compounds according to any of claims 1 to 11, and an inert carrier and/or diluent.

Claim 20

The method according to claim 16, wherein the application is effected in a field of wheat or barley.

Claim 21

The method according to claim 16, wherein the application is effected in a field of soybean or peanut. -

Claim 22

Use of the compounds according to any of claims 1 to 11 as herbicides.