US4398943A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Triazolinone derivative and herbicidal use thereof
Assignee: Nihon Nohyaku Co Ltd
•
Filing: 1981-12-15
•
Granted: 1983-08-16
•
Expires: 2001-12-15
Abstract
Abstract There is provided a new herbicidal compound of the formula, <IMAGE> wherein R1 is an alkyl group; R2 is an alkynyl group, a halomethyl group, or a haloethyl group; and X is an alkoxy group, an alkenyloxy group, an alkoxy-alkoxy group, an alkynyloxy group, a hydroxy group, a halomethyloxy group, or a haloethyloxy group.
Inventors
- 👤 Mitsuru Kajioka
- 👤 Katsumasa Okawa
- 👤 Kuniaki Taninaka
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 14:22
CPC Classifications
A; A01; A01N; A01N43/00; A01N43/64; A01N43/647; A01N43/653; A01N47/00; A01N47/02; C; C07; C07D; C07D249/00; C07D249/02; C07D249/08; C07D249/10; C07D249/12
Claims Analysis
Total Claims: 44
Claim 1
Independent Claim
86 words
A Δ 2 -1,2,4-triazoline-5-one derivative represented by the formula (I) ##STR24## wherein R 1 is a C 1 -C 4 alkyl group; R 2 is a C 3 -C 5 alkynyl group, a halomethyl group, or a haloethyl group; and X is a C 1 -C 4 alkoxy group, a C 2 -C 6 alkenyloxy group, a C 2 -C 6 alkoxyalkoxy group, a C 3 -C 8 alkynyloxy group, a hydroxy group, a halomethyloxy group, a 3-chloro-2-propenoxy group, a 1-ethynyl-1-cyclohexyloxy group, or a halethyloxy group.
Claim 2
Dependent Claim
86 words
A Δ 2 -1,2,4-triazoline-5-one derivative represented by the formula (I) ##STR24## wherein R 1 is a C 1 -C 4 alkyl group; R 2 is a C 3 -C 5 alkynyl group, a halomethyl group, or a haloethyl group; and X is a C 1 -C 4 alkoxy group, a C 2 -C 6 alkenyloxy group, a C 2 -C 6 alkoxyalkoxy group, a C 3 -C 8 alkynyloxy group, a hydroxy group, a halomethyloxy group, a 3-chloro-2-propenoxy group, a 1-ethynyl-1-cyclohexyloxy group, or a halethyloxy group.
Claim 3
Dependent Claim
15 words
A Δ 2 -1,2,4-triazolin-5-one derivative of claim 1, wherein R 2 is the halomethyl group.
Claim 4
Dependent Claim
16 words
A Δ 2 -1,2,4-triazolin-5-one derivative of claim 2, wherein the halomethyl group is a difluoromethyl group.
Claim 5
Dependent Claim
46 words
A Δ 2 -1,2,4-triazolin-5-one derivative of claim 1, wherein X is a C 1 -C 4 alkoxy group, a C 2 -C 6 alkenyloxy group, a C 2 -C 6 alkoxyalkoxy group, a 3-chloro-2-propenoxy group, a 1-ethynyl-1-cyclohexyloxy group, or a C 3 -C 8 alkynyloxy group.
Claim 6
Dependent Claim
53 words
A Δ 2 -1,2,4-triazolin-5-one derivative of claim 1, wherein R 2 is a halomethyl group; and X is a C 1 -C 4 alkoxy group, a C 2 -C 6 alkenyloxy group, a 3-chloro-2-propenoxy group, a 1-ethynyl-1-cyclohexyloxy group, a C 2 -C 6 alkoxyalkoxy group, or a C 3 -C 8 alkynyloxy group.
Claim 7
Dependent Claim
16 words
A Δ 2 -1,2,4-triazolin-5-one derivative of claim 5, wherein the halomethyl group is a diflouromethyl group.
Claim 8
Dependent Claim
3 words
1(2,4-dichloro-5-isopropoxyphenyl)-3-methyl-4-difluromethyl-Δ 2 -1,2,4-triazolin-5one.
Claim 9
Dependent Claim
3 words
1(2,4-dichloro-5-isopropoxyphenyl)-3-methyl-4-difluromethyl-Δ 2 -1,2,4-triazolin-5one.
Claim 10
Dependent Claim
3 words
1-(2,4-dichloro-5-allyloxyphenyl)-3-methyl-4-difluromethyl-Δ 2 -1,2,4-triazolin-5-one.
Claim 11
Dependent Claim
3 words
1-(2,4-dichloro-5-allyloxyphenyl)-3-methyl-4-difluromethyl-Δ 2 -1,2,4-triazolin-5-one.
Claim 12
Dependent Claim
3 words
1-(2,4-dichloro-5-propargyloxyphenyl)-3-methyl-4-difluromethyl-Δ 2 -1,2,4-triazolin-5-one.
Claim 13
Dependent Claim
3 words
1-(2,4-dichloro-5-propargyloxyphenyl)-3-methyl-4-difluromethyl-Δ 2 -1,2,4-triazolin-5-one.
Claim 14
Dependent Claim
3 words
1-(2,4-dichloro-5-methoxymethoxyphenyl)-3-methyl-4-difluoromethyl-Δ 2 -1,2,4-triazolin-5-one.
Claim 15
Dependent Claim
3 words
1-(2,4-dichloro-5-methoxymethoxyphenyl)-3-methyl-4-difluoromethyl-Δ 2 -1,2,4-triazolin-5-one.
Claim 16
Dependent Claim
98 words
A herbicidal composition comprising an effective amount of a Δ 2 -1,2,4-triazolin-5-one derivative and a diluent, said derivative being represented by the formula ##STR25## wherein R 1 is a C 1 -C 4 alkyl group; R 2 is a C 3 -C 5 alkynyl group, a halomethyl group, or a haloethyl group; and X is C 1 -C 4 alkoxy group, a C 2 -C 6 alkenyloxy group, a C 2 -C 6 alkoxyalkoxy group, a C 3 -C 8 alkynyloxy group, a hydroxy group, a halomethyloxy group, a 3-chloro-2-propenoxy group, a 1-ethynyl-1-cyclohexyloxy group, or a haloethyloxy group.
Claim 17
Dependent Claim
98 words
A herbicidal composition comprising an effective amount of a Δ 2 -1,2,4-triazolin-5-one derivative and a diluent, said derivative being represented by the formula ##STR25## wherein R 1 is a C 1 -C 4 alkyl group; R 2 is a C 3 -C 5 alkynyl group, a halomethyl group, or a haloethyl group; and X is C 1 -C 4 alkoxy group, a C 2 -C 6 alkenyloxy group, a C 2 -C 6 alkoxyalkoxy group, a C 3 -C 8 alkynyloxy group, a hydroxy group, a halomethyloxy group, a 3-chloro-2-propenoxy group, a 1-ethynyl-1-cyclohexyloxy group, or a haloethyloxy group.
Claim 18
Dependent Claim
13 words
A herbidical composition of claim 11, wherein R 2 is a halomethyl group.
Claim 19
Dependent Claim
14 words
A herbidical composition of claim 12, wherein the halomethyl group is a difluoromethyl group.
Claim 20
Dependent Claim
44 words
A herbicidal composition of claim 11, wherein X is a C 1 -C 4 alkoxy group, a C 2 -C 6 alkenyloxy group, a C 2 -C 6 alkoxyalkoxy group, a 3-chloro-2-propenoxy group, a 1-ethynyl-1-cyclohexyloxy group, or a C 3 -C 8 alkynyloxy group.
Claim 21
Dependent Claim
51 words
A herbicidal composition of claim 11, wherein R 2 is a halomethyl group; and X is a C 1 -C 4 alkoxy group, a C 2 -C 6 alkenyloxy group, a C 2 -C 6 alkoxyalkoxy group, a 3-chloro-2-propenoxy group, a 1-ethynyl-1-cyclohexyloxy group, or a C 3 -C 8 alkynyloxy group.
Claim 22
Dependent Claim
14 words
A herbicidal composition of claim 15, wherein the halomethyl group is a difluoromethyl group.
Claim 23
Dependent Claim
16 words
A herbicidal composition of claim 11, wherein the Δ 2 -1,2,4-triazolin-5-one derivative is 1-(2,4-dichloro-5-isopropoxyphenyl)-3-methyl-4-difluromethyl-Δ 2 -1,2,4-triazolin-5-one.
Claim 24
Dependent Claim
16 words
A herbicidal composition of claim 11, wherein the Δ 2 -1,2,4-triazolin-5-one derivative is 1-(2,4-dichloro-5-allyloxyphenyl)-3-methyl-4-difluoromethyl-Δ 2 -1,2,4-triazolin-5-one.
Claim 25
Dependent Claim
15 words
A herbicidal composition of claim 11, wherein the Δ 2 -1,2,4-triazolin-5-one derivative is 1-(2,4-dichloro-5-propargyloxyphenyl)-3-methyl-4-difluoromethyl-Δ.sup.2 -1,2,4-triazolin-5-one.
Claim 26
Dependent Claim
15 words
A herbicidal composition of claim 11, wherein the Δ 2 -1,2,4-triazolin-5-one derivative is 1-(2,4-dichloro-5-methoxymethoxyphenyl)-3-methyl-4-difluromethyl-Δ.sup.2 -1,2,4-triazolin-5-one.
Claim 27
Dependent Claim
21 words
A method of killing plants comprising applying to the plants a herbicidally effective amount of a compound according to claim 1.
Claim 28
Dependent Claim
21 words
A method of killing plants comprising applying to the plants a herbicidally effective amount of a compound according to claim 2.
Claim 29
Dependent Claim
21 words
A method of killing plants comprising applying to the plants a herbicidally effective amount of a compound according to claim 3.
Claim 30
Dependent Claim
21 words
A method of killing plants comprising applying to the plants a herbicidally effective amount of a compound according to claim 4.
Claim 31
Dependent Claim
21 words
A method of killing plants comprising applying to the plants a herbicidally effective amount of a compound according to claim 5.
Claim 32
Dependent Claim
20 words
A method of killing plants comprising applying to the plants a herbicidally effective amount of the compound of claim 6.
Claim 33
Dependent Claim
20 words
A method of killing plants comprising applying to the plants a herbicidally effective amount of the compound of claim 7.
Claim 34
Dependent Claim
20 words
A method of killing plants comprising applying to the plants a herbicidally effective amount of the compound of claim 8.
Claim 35
Dependent Claim
20 words
A method of killing plants comprising applying to the plants a herbicidally effective amount of the compound of claim 9.
Claim 36
Dependent Claim
20 words
A method of killing plants comprising applying to the plants a herbicidally effective amount of the compound of claim 10.
Claim 37
Dependent Claim
16 words
A method according to claim 21 wherein the compound is applied before emergence of the plants.
Claim 38
Dependent Claim
16 words
A method according to claim 21 wherein the compound is applied after emergence of the plants.
Claim 39
Dependent Claim
37 words
A method of selectively killing weeds in a crop of useful plants comprising applying to the crop an amount of a compound of claim 1 effective to kill the weeds but insufficient to kill the useful crop.
Claim 40
Dependent Claim
16 words
A method according to claim 33 wherein the herbicide is applied efore emergence of the plants.
Claim 41
Dependent Claim
11 words
A method according to claim 34 wherein the crop is rice.
Claim 42
Dependent Claim
16 words
A method according to claim 33 wherein the herbicide is applied after emergence of the plants.
Claim 43
Dependent Claim
13 words
A method according to claim 36 wherein the crop is rice or soybeans.
Claim 44
Dependent Claim
10 words
A compound according to claim 5 wherein X is 1-ethynyl-1-cyclohexyloxy.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-08-15 | 1987-02-14 | 1987-08-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-08-15 | 1991-02-14 | 1991-08-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-08-15 | 1995-02-14 | 1995-08-16 | $7700.00 | Window Closed / Lapsed |