EP0049508A1
Expired / Lapsed
EP
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N-(3-Substituted oxyphenyl) tetrahydrophthalimides and herbicidal composition
Assignee: Mitsubishi Chemical Corp
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Filing: 1981-10-05
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Granted: —
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Expires: 2001-10-05
Abstract
Abstract Δ'-Tetrahydrophthalimides having a substituted oxy group at 3-position and, if necessary, a halogen atom at 4-position and/or at 2-position of phenyl group as N-substituent have excellent herbicidal activity and are useful as selective herbicides.
Inventors
- 👤 Tetsuo Jikuhara
- 👤 Masatsugu Oda
- 👤 Bunji Natsume
- 👤 Hisao Watanabe
- 👤 Seiichi Suzuki
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-04 17:30
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/44; C07D209/48; A; A01; A01N; A01N39/00; A01N39/02; A01N39/04
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
173 words
1) N-(3-substituted oxyphenyl)-3,4,5,6-tetrahydrophthalimides which are represented by the general formula wherein X and Y respectively represent hydrogen or a halogen atom; A represents B represents or -CN; R 1 represents hydrogen atom or an alkyl, phenyl or a substituted phenyl group; R2 represents hydrogen atom or an alkyl group; R 3 represents hydrogen, atom or an alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, cyanoalkyl, hydroxyalkyl, alkoxyalkyl, alkoxyalkoxyalkyl, alkoxyalkoxyalkoxyalkyl, alkylthioalkyl, cycloalkyl, aralkyl, phenyl, y-butyrolactone group which can be substituted by methyl group or salt moiety; R 4 represents an alkyl, alkoxycarbonylalkyl or benzyl group; R 5 represents hydrogen atom or methyl group; R 6 represents methyl or phenyl group; R 7 and R 8 can be the same or different and respectively represent hydrogen atom, an alkyl, alkenyl, alkynyl, haloalkyl, hydroxyalkyl, alkoxyalkyl, aralkyl, phenyl, substituted phenyl, heterocyclic ring, alkoxy, alkenyloxy, amino, mono-substituted amino, di-substituted amino, alkanesulfonyl, benzenesulfonyl, substituted benzenesulfonyl or cycloalkyl group; and R 8 can form a heterocyclic ring which can have -0-; and m and n respectively represent an integer of 1 to 3.
Claim 2
Dependent Claim
173 words
1) N-(3-substituted oxyphenyl)-3,4,5,6-tetrahydrophthalimides which are represented by the general formula wherein X and Y respectively represent hydrogen or a halogen atom; A represents B represents or -CN; R 1 represents hydrogen atom or an alkyl, phenyl or a substituted phenyl group; R2 represents hydrogen atom or an alkyl group; R 3 represents hydrogen, atom or an alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, cyanoalkyl, hydroxyalkyl, alkoxyalkyl, alkoxyalkoxyalkyl, alkoxyalkoxyalkoxyalkyl, alkylthioalkyl, cycloalkyl, aralkyl, phenyl, y-butyrolactone group which can be substituted by methyl group or salt moiety; R 4 represents an alkyl, alkoxycarbonylalkyl or benzyl group; R 5 represents hydrogen atom or methyl group; R 6 represents methyl or phenyl group; R 7 and R 8 can be the same or different and respectively represent hydrogen atom, an alkyl, alkenyl, alkynyl, haloalkyl, hydroxyalkyl, alkoxyalkyl, aralkyl, phenyl, substituted phenyl, heterocyclic ring, alkoxy, alkenyloxy, amino, mono-substituted amino, di-substituted amino, alkanesulfonyl, benzenesulfonyl, substituted benzenesulfonyl or cycloalkyl group; and R 8 can form a heterocyclic ring which can have -0-; and m and n respectively represent an integer of 1 to 3.
Claim 3
Dependent Claim
16 words
2) The compound (I) according to Claim 1 wherein X represents Cℓ and Y represents H.
Claim 4
Dependent Claim
16 words
3) The compound (I) according to Claim 1 wherein X represents Br and Y represents H.
Claim 5
Dependent Claim
77 words
4) The compound (I) according to Claim 1, 2 or 3 wherein A represents -CHR 1 -; R 1 represents H, an alkyl or phenyl group; B represents -CONR 7 R 8 group; R 7 and R 8 respectively represent H, an alkyl, alkenyl, alkynyl, haloalkyl, hydroxyalkyl, alkoxyalkyl, aralkyl, phenyl, substituted phenyl, heterocyclic ring, alkoxy, alkenyloxy, amino; mono-substituted amino, di-substituted amino, alkanesulfonyl, benzenesulfonyl, substituted benzenesulfonyl or cycloalkyl group; can form a heterocyclic ring which can have -O-.
Claim 6
Dependent Claim
63 words
5) The compound (I) according to Claim 4 wherein R 1 represents a C 1-4 alkyl group; R 7 represents H, a C 1-7 alkyl or a C 1-4 alkoxy group ; R 8 represents a C 1-7 alkyl, a C 1-4 alkoxy, a C 2-4 haloalkyl, a C 2-4 hydroxyalkyl, phenyl, aralkyl, a C 3-4 alkenyl or a C 3-5 alkynyl group.
Claim 7
Dependent Claim
56 words
6) The compound (I) according to Claim 5 wherein R 1 represents a C 1-4 alkyl group; R 7 represents H, a C l -7 alkyl or a C 1-4 alkoxy group; R 8 represents a C 1-7 alkyl, a C 1-4 alkoxy, a C 3-4 alkenyl, a C 3 - 5 alkynyl or benzyl group.
Claim 8
Dependent Claim
49 words
7) The compound (I) according to Claim 6 wherein X represents Cℓ or Br; Y represents H; R 1 represents a C 1-3 alkyl group; R 7 represents H, methyl or methoxy group; R 8 represents a C 1-4 alkyl, a C 1-4 alkoxy, allyl, propargyl or benzyl group.
Claim 9
Dependent Claim
134 words
8) The compound (I) according to Claim 1, 2 or 3 wherein A represents or -CH 2 CH=CH-; B represents R 1 represents hydrogen atom or an alkyl, phenyl or a substituted phenyl group; R 2 represents hydrogen atom or an alkyl group; R 3 represents hydrogen atom or an alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, cyanoalkyl, hydroxyalkyl, alkoxyalkyl, alkoxyalkoxyalkyl, alkoxyalkoxyalkoxyalkyl, alkylthioalkyl, cycloalkyl, aralkyl, phenyl, γ-butyrolactone group which can be substituted by methyl group or a salt moiety selected from alkali metals, alkaline earth metals and ammonium group which can be substituted with an alkyl group; R 4 represents an alkyl, alkoxycarbonyl or benzyl group; R represents hydrogen atom or methyl group; R 6 represents methyl or phenyl group; n is an integer of 1 to 3; m is an integer of 1 to 3.
Claim 10
Dependent Claim
46 words
9) The compound (I) according to Claim 8 wherein A represents -CHR 1- ; R 1 represents a C 1-4 alkyl or phenyl group; B represents -COOR or -COSR ; R 3 represents a C 1-6 alkyl group; R 4 represents a C 1-10 alkyl group.
Claim 11
Dependent Claim
26 words
10) The compound (I) according to Claim 9 wherein R 3 represents a C 1-4 alkyl group; and R 4 represents a C 2-3 alkyl group.
Claim 12
Dependent Claim
40 words
11) The compound (I) according to Claim 1, 2 or 3 wherein A represents -(CHR 1 ) n ; R 1 represents H or an alkyl group; n is an integer of 1 to 3 and B represents CN group.
Claim 13
Dependent Claim
20 words
12) A herbicidal composition which comprises the compound (1) according to Claim 1 as an active ingredient and a carrier.
Claim 14
Dependent Claim
16 words
13) The herbicidal composition according to Claim 12 wherein X represents Br and Y represents H.
Claim 15
Dependent Claim
76 words
14) The herbicidal composition according to Claim 12 or 13 wherein A represents -CHR 1 -; R 1 represents H, an alkyl or phenyl group; B represents -CONR 7 R 8 group; R 7 and R 8 respectively represent H, an alkyl, alkenyl, alkynyl, haloalkyl, hydroxyalkyl, alkoxyalkyl, aralkyl, phenyl, substituted phenyl, heterocyclic ring, alkoxy, alkenyloxy, amino, mono-substituted amino, di-substituted amino, alkanesulfonyl, benzenesulfonyl, substituted benzenesulfonyl or cycloalkyl group; can form a heterocyclic ring which can have -O-.
Claim 16
Dependent Claim
47 words
15) The herbicidal composition according to Claim 14 wherein X represents Cℓ; Y represents H; R 1 represents a C 1-3 alkyl group; R 7 represents H, methyl or methoxy group; R 8 represents a C 1-4 alkyl, a C 1-4 alkoxy, allyl, propargyl or benzyl group.
Claim 17
Dependent Claim
133 words
16) The herbicidal composition according to Claim 12 or 13 A represents or -CH 2 CH=CH-; B represents R 1 represents hydrogen atom or an alkyl, phenyl or a substituted phenyl group; R 2 represents hydrogen atom or an alkyl group; R 3 represents hydrogen atom or an alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, cyanoalkyl, hydroxyalkyl, alkoxyalkyl, alkoxyalkoxyalkyl, alkoxyalkoxyalkoxyalkyl, alkylthioalkyl, cycloalkyl, aralkyl, phenyl, γ-butyrolactone group which can be substituted by methyl group or a salt moiety selected from alkali metals alkaline earth metals and ammonium group which can be substituted with an alkyl group; R 4 represents an alkyl, alkoxycarbonyl or benzyl group; R 5 represents hydrogen atom or methyl group; R 6 represents methyl or phenyl group; n is an integer of 1 to 3; m is an integer of 1 to 3.
Claim 18
Dependent Claim
38 words
17) The herbicidal composition according to Claim 16 wherein R 1 represents a C 1-4 alkyl group; R 2 represents H; R 3 represents a C 1-4 alkyl group; and R 4 represents a C 2-3 alkyl group.
Claim 19
Dependent Claim
39 words
18) The herbicidal composition according to Claim 12 or 13 wherein A represents -(CHR 1 ) n ; R 1 represents H or an alkyl group; n is an integer of 1 to 3 and B represents CN group.
Claim 20
Dependent Claim
45 words
19) The herbicidal composition according to one of Claim 9 to 14 which is in a form of a wettable powder, a flowable, a granule or an emulsifiable concentrate which comprises the compound (I) as an active ingredient and an inert solid or liquid carrier.
Claim 21
Dependent Claim
26 words
20) The herbicidal composition according to one of Claim 9 to 15 which comprises 5 to 80 wt.% of the compound (I) as an active ingredient.
Claim 22
Dependent Claim
25 words
21) A method of controlling weeds in a cultivation of a crop plant by applying an effective amount of the compound (I) of Claim 1.
Claim 23
Dependent Claim
32 words
22) The method of controlling weeds in a cultivation of a crop plant selected from soybean, cotton, sugar beat, sunflower, pea, potato, cucumber, rice, wheat, barley, oat, rye, corn and sugar cane.
Claim 24
Dependent Claim
32 words
22) The method of controlling weeds in a cultivation of a crop plant selected from soybean, cotton, sugar beat, sunflower, pea, potato, cucumber, rice, wheat, barley, oat, rye, corn and sugar cane.
Claim 25
Dependent Claim
73 words
23) A process for producing the compound (I) of Claim 1 which comprises (a) reacting a compound having the formula with a compound having the formula Z-A-B; or (b) reacting a compound having the formula with a compound having the formula and if necessary converting a substituent -A-B of the product to the other -A-B to produce the compound having the formula wherein X, Y, A and B are defined in Claim 1.
References Cited (Backward Citations)
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