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N-(3-substituted aminophenyl) tetrahydrophthalimides and herbicidal composition

Assignee: Mitsubishi Chemical Corp
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Filing: 1982-10-05
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Granted: —
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Expires: 2002-10-05
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Abstract

Abstract Novel tetrahydrophthalimides are represented by the general formula (1): wherein A is a hydrogen atom or a methyl group, X is a hydrogen atom, a halogen atom, a methyl group or a methoxy group, each of Y and Z is a hydrogen atom or a halogen atom, each of U and V is a hydrogen atom; a group; an alkyl group; an alkyl group having one or two substituents selected from the group consitsing of a halogen atom, an alkoxy group, a cyano group and an aryl group which may be substituted by a halogen atom; an alkenyl group; an alkenyl group having one or two substituents selected from the group consitsing of an alkoxycarbonyl group and a cyano group; an alkynyl group; a . group; or an alkylsulfonyl group, The novel compounds are useful as herbicides.

Inventors

  • 👤 Tetsuo Jukihara
  • 👤 Kazuyuki Ushinohama
  • 👤 Bunzi Natsume
  • 👤 Hisao Watanabe
  • 👤 Seiichi Suzuki

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-10-24 16:45
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/44; C07D209/48; A; A01; A01N; A01N37/00; A01N37/18; A01N37/32; A01N37/44; A01N37/46; A01N41/00; A01N41/02; A01N41/04; A01N41/06; A01N43/00; A01N43/72; A01N43/80; A01N47/00; A01N47/08; A01N47/10; A01N47/20; A01N47/22; A01N47/28; A01N47/30

Claims Analysis

Total Claims: 27
Claim 1
Independent Claim 371 words
1) A tetrahydrophthalimide represented by the general formula (I): wherein A is a hydrogen atom or a methyl group, X is a hydrogen atom, a halogen atom, a methyl group or a methoxy group, each of Y and Z is a hydrogen atom or a halogen atom, each of U and V is a hydrogen atom; a group; an alkyl group; an alkyl group having one or two substituents selected from the group consitsing of a halogen atom, an alkoxy group, a cyano group and an aryl group which may be substituted by a halogen atom; an alkenyl group; an alkenyl group having one or two substituents selected from the group consitsing of an alkoxycarbonyl group and a cyano group; an alkynyl group; group; or an alkylsulfonyl group, R is a hydrogen atom or a methyl group, n is an integer of from 1 to 6, B is -O R 3 , -SR 4 or E is -R 7 , -OR 8, -SR 9 , or a hydrogen atom, R 3 is a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, an aryl group, an aralkyl group or R 4 is an alkyl group, each of R 5 and R 6 is a hydrogen atom, an alkyl group, an alkoxy group, an alkoxyalkyl group, an alkenyl group, an alkynyl group, an aryl group, an aralkyl group, a cycloalkyl group, an alkylsulfonyl group or or is a heterocyclic group which may include an oxygen atom, R 7 is an alkyl group which may be substituted by one or more halogen atoms; an alkenyl group; or an aryl group which may be substituted by a halogen atom, R 8 is an alkyl group, a cycloalkyl group, an aralkyl group or an aryl group, R 9 is an alkyl group or an aryl group, each of R 10 and R 11 is a hydrogen atom, an alkyl group, an alkoxy group or an aryl group which may be substituted by a halogen atom, R 12 is a hydrogen atom or an alkyl group, and D is a hydroxyl group, an alkoxy group or an amino group which may be substituted by one or two alkyl or alkenyl groups.
Claim 2
Dependent Claim 371 words
1) A tetrahydrophthalimide represented by the general formula (I): wherein A is a hydrogen atom or a methyl group, X is a hydrogen atom, a halogen atom, a methyl group or a methoxy group, each of Y and Z is a hydrogen atom or a halogen atom, each of U and V is a hydrogen atom; a group; an alkyl group; an alkyl group having one or two substituents selected from the group consitsing of a halogen atom, an alkoxy group, a cyano group and an aryl group which may be substituted by a halogen atom; an alkenyl group; an alkenyl group having one or two substituents selected from the group consitsing of an alkoxycarbonyl group and a cyano group; an alkynyl group; group; or an alkylsulfonyl group, R is a hydrogen atom or a methyl group, n is an integer of from 1 to 6, B is -O R 3 , -SR 4 or E is -R 7 , -OR 8, -SR 9 , or a hydrogen atom, R 3 is a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, an aryl group, an aralkyl group or R 4 is an alkyl group, each of R 5 and R 6 is a hydrogen atom, an alkyl group, an alkoxy group, an alkoxyalkyl group, an alkenyl group, an alkynyl group, an aryl group, an aralkyl group, a cycloalkyl group, an alkylsulfonyl group or or is a heterocyclic group which may include an oxygen atom, R 7 is an alkyl group which may be substituted by one or more halogen atoms; an alkenyl group; or an aryl group which may be substituted by a halogen atom, R 8 is an alkyl group, a cycloalkyl group, an aralkyl group or an aryl group, R 9 is an alkyl group or an aryl group, each of R 10 and R 11 is a hydrogen atom, an alkyl group, an alkoxy group or an aryl group which may be substituted by a halogen atom, R 12 is a hydrogen atom or an alkyl group, and D is a hydroxyl group, an alkoxy group or an amino group which may be substituted by one or two alkyl or alkenyl groups.
Claim 3
Dependent Claim 56 words
2) The tetrahydrophthalimide according to Claim 1 which is represented by the general formula (II): O wherein V 1 is a hydrogen atom, an alkyl group, a - -R 7 , and A, B, n, X, Y, Z, R 1 , R 2 and R 7 are as defined with respect to the general formula (I).
Claim 4
Dependent Claim 19 words
3) The tetrahydrophthalimide according to Claim 2 wherein V 1 in the general formula (II) is a hydrogen atom.
Claim 5
Dependent Claim 34 words
4) The tetrahydrophthalimide according to Claim 3 which is represented by the general formula (VII): wherein X, Y, R 1 , R5and R 6 are as defined with respect to the general formula (I).
Claim 6
Dependent Claim 37 words
5) The tetrahydrophthalimide according to any one of Claims 1 to 4 wherein in the general formula (I), X is a chlorine atom or a bromine atom, and Y is a hydrogen atom or a fluorine atom.
Claim 7
Dependent Claim 64 words
6) The tetrahydrophthalimide according to Claim 4 wherein in the general formula (VII), X is a chlorine atom or a bromine atom, Y is a hydrogen atom or a fluorine atom, R 1 is an alkyl group having from 1 to 3 carbon atoms, R 5 is a hydrogen atom and R 6 is an alkyl group having from 1 to 5 carbon atoms.
Claim 8
Dependent Claim 73 words
7) The tetrahydrophthalimide according to Claim 4 wherein in the general formula (VII), X is a chlorine atom or a bromine atom, Y is a hydrogen atom or a fluorine atom, R 1 is an alkyl group having from 1 to 3 carbon atoms, R 5 is an alkyl or alkoxy group having from 1 to 3 carbon atoms and R 6 is an alkyl group having from 1 to 3 carbon atoms.
Claim 9
Dependent Claim 35 words
8) The tetrahydrophthalimide according to Claim 1, 2 or 3 which is represented by the general formula (VIII): wherein Y, R 1 and R 3 are as defined with respect to the general formula (I).
Claim 10
Dependent Claim 59 words
9) The tetrahydrophthalimide according to Claim 8 wherein in the general formula (VIII), Y is a hydrogen atom or a fluorine atom, R 1 is an alkyl group having from 1 to 4 carbon atoms and R 3 is an alkyl group having from 1 to 5 carbon atoms or an alkenyl group having 3 or 4 carbon atoms.
Claim 11
Dependent Claim 66 words
10) The tetrahydrophthalimide according to Claim 1 which is represented by the general formula (IV): wherein each of U 2 and V 2 is a hydrogen atom; an alkyl group; an alkyl group substituted by a halogen atom, an alkoxy group or a cyano group; an alkenyl group or an alkynyl group, provided one of U 2 and V 2 is other than a hydrogen atom.
Claim 12
Dependent Claim 40 words
11) The tetrahydrophthalimide according to Claim 1 which is represented by the general formula (V): wherein U 3 is a group where R is as defined with respect to the general formula (I), and V 3 is an alkyl group.
Claim 13
Dependent Claim 19 words
12) A herbicidal composition which comprises the tetrahydrophthalimide of Claim 1 as an active ingredient and an inert carrier.
Claim 14
Dependent Claim 18 words
13) The herbicidal composition according to Claim 12 wherein the active ingredient is the tetrahydrophthalimide of Claim 2.
Claim 15
Dependent Claim 18 words
14) The herbicidal composition according to Claim 12 wherein the active ingredient is the tetrahydrophthalimide of Claim 3.
Claim 16
Dependent Claim 18 words
15) The herbicidal composition according to Claim 12 wherein the active ingredient is the tetrahydrophthalimide of Claim 4.
Claim 17
Dependent Claim 18 words
16) The herbicidal composition according to Claim 12 wherein the active ingredient is the tetrahydrophthalimide of Claim 5.
Claim 18
Dependent Claim 18 words
17) The herbicidal composition according to Claim 12 wherein the active ingredient is the tetrahydrophthalimide of Claim 6.
Claim 19
Dependent Claim 18 words
18) The herbicidal composition according to Claim 12 wherein the active ingredient is the tetrahydrophthalimide of Claim 7.
Claim 20
Dependent Claim 18 words
19) The herbicidal composition according to Claim 12 wherein the active ingredient is the tetrahydrophthalimide of Claim 8.
Claim 21
Dependent Claim 18 words
20) The herbicidal composition according to Claim 12 wherein the active ingredient is the tetrahydrophthalimide of Claim 9.
Claim 22
Dependent Claim 18 words
21) The herbicidal composition according to Claim 12 wherein the active ingredient is the tetrahydrophthalimide of Claim 10.
Claim 23
Dependent Claim 18 words
22) The herbicidal composition according to Claim 12 wherein the active ingredient is the tetrahydrophthalimide of Claim 11.
Claim 24
Dependent Claim 47 words
23) The herbicidal composition according to Claim 12 which comprises from 1 to 80% by weight of the active ingredient, from 2 to 30% by weight of a surfactant, from 10 to 97% of an inert carrier and from 0 to 20% by weight of other additives.
Claim 25
Dependent Claim 26 words
24) The herbicidal composition according to Claim 12 which is formulated in a form of an emulsifiable concentrate, a wettable powder, a dust, granules or tablets.
Claim 26
Dependent Claim 150 words
25) A process for producing a tetrahydrophthalimide represented by the general formula (I): wherein A, X, Y, Z, U and V are as defined in Claim 1, which comprises: (a) reacting a tetrahydrophthalic acid anhydride represented by the general formula: wherein A is as defined with respect to the general formula (I), with an aniline represented by the general formula: wherein X, Y, Z, U and V are as defined with respect to the general formula (I); or (b) reacting a compound represented by the general formula: wherein A, X, Y, Z and V are as defined with respect to the general formula (I), with a compound represented by the general formula: wherein U is as defined with respect to the general formula (I) and Q is a halogen atom, mesyl, tosyl or an alkoxy group, or Q forms .together with U an acid anhydride or a mixed acid anhydride.
Claim 27
Dependent Claim 26 words
26) A method for controlling undesirable weeds which comprises applying a herbicidally effective amount of a tetrahydrophthalimide of the formula (I) as defined in Claim 1.

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