US3830642A
Expired / Lapsed
US
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Method for controlling weeds with 1{40 -formyl-1{40 -halobenzeneazomethanes and formulations therefor
Assignee: Pharmacia and Upjohn Co
•
Filing: 1971-04-28
•
Granted: 1974-08-20
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Expires: 1991-04-28
Abstract
Abstract Some new 1''-formyl-1''-halobenzeneazomethanes have been prepared. The compounds are active as herbicides. There is variable activity against arthropod pests from compound to compound. The 1''-formyl group can be substituted so as to form a keto or ester functional group. Alkyl, haloalkyl, and cycloalkyl substituent groups form ketones according to the invention. Alkoxy, haloalkoxy, and cycloalkoxy substituent groups form esters according to the invention. The 1''-halogen can be bromine, chlorine, or fluorine; and the benzene ring of the azobenzene group can be variously substituted with halogens (preferred), alkyl, alkoxy, and haloalkyl groups. In addition, the methyl carbon (1''-position) can have another halogen atom substituent, or an alkyl, haloalkyl, cycloalkyl, or phenyl substituent group. The invention comprehends the use of the new 1''-formyl-1''halobenzeneazomethanes as herbicides, and further comprehends new formulations for effecting the new use. Both a method of using and herbicidal formulations of the new 1''-formyl-1''halobenzeneazomethanes are described.
Inventors
- 👤 M Moon
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 23:11
CPC Classifications
C; C07; C07C; C07C251/00; C07C251/72
Claims Analysis
Total Claims: 52
Claim 1
Independent Claim
10 words
The method according to claim 1 wherein R is alkyl.
Claim 2
Dependent Claim
10 words
The method according to claim 2 wherein R'' is X.
Claim 3
Dependent Claim
11 words
The method according to claim 3 wherein the X''s are chlorine.
Claim 4
Dependent Claim
11 words
The method according to claim 4 wherein a Y is halogen.
Claim 5
Dependent Claim
11 words
The method according to claim 5 wherein the halogen is chlorine.
Claim 6
Dependent Claim
10 words
The method according to claim 6 wherein m is 3.
Claim 7
Dependent Claim
7 words
The method according to claim 7, 1,1-dichloro-1-((4,6-dichloro-o-tolyl)azo)-2-propanone.
Claim 8
Dependent Claim
10 words
The method according to claim 1 wherein R is alkoxy.
Claim 9
Dependent Claim
10 words
The method according to claim 9 wherein R'' is alkyl.
Claim 10
Dependent Claim
12 words
The method according to claim 10 wherein X is chlorine or fluorine.
Claim 11
Dependent Claim
12 words
The method according to claim 11 wherein m is 3 or 4.
Claim 12
Dependent Claim
14 words
The method according to claim 12 wherein m is 3 and Y is halogen.
Claim 13
Dependent Claim
11 words
The method according to claim 13 wherein the halogen is chlorine.
Claim 14
Dependent Claim
8 words
The method according to claim 14, ethyl 2-chloro-2-((2,4,6-trichlorophenyl)azo)propionate.
Claim 15
Dependent Claim
8 words
The method according to claim 14, ethyl 2-chloro-2-((2,4,6-trichlorophenyl)azo)butyrate.
Claim 16
Dependent Claim
12 words
The method according to claim 9 wherein R'' is an X halogen.
Claim 17
Dependent Claim
12 words
The method according to claim 17 wherein X and R'' are chlorine.
Claim 18
Dependent Claim
10 words
The method according to claim 18 wherein Y is halogen.
Claim 19
Dependent Claim
10 words
The method according to claim 19 wherein Y is chlorine.
Claim 20
Dependent Claim
8 words
The method according to claim 20, ethyl dichloro-((2,4,6-trichlorophenyl)azo)acetate.
Claim 21
Dependent Claim
8 words
The method according to claim 20, ethyl dichloro-((2,4-dichlorophenyl)azo)acetate.
Claim 22
Dependent Claim
12 words
The method according to claim 18 wherein (Y)m is halogen and lower-alkyl.
Claim 23
Dependent Claim
12 words
The method according to claim 23 wherein (Y)m is chlorine and lower-alkyl.
Claim 24
Dependent Claim
10 words
The method according to claim 24 wherein lower-alkyl is methyl.
Claim 25
Dependent Claim
8 words
The method according to claim 25, methyl dichloro-((2,6-dichloro-p-tolyl)azo)acetate.
Claim 26
Dependent Claim
8 words
The method according to claim 26, methyl dichloro-((2,4,6-trichloro-m-tolyl)azo)acetate.
Claim 27
Dependent Claim
10 words
The method according to claim 9 wherein R'' is phenyl.
Claim 28
Dependent Claim
10 words
The method according to claim 28 wherein X is chlorine.
Claim 29
Dependent Claim
10 words
The method according to claim 29 wherein Y is halogen.
Claim 30
Dependent Claim
10 words
The method according to claim 30 wherein Y is chlorine.
Claim 31
Dependent Claim
9 words
The method according to claim 31, methyl chlorophenyl-((2,4, 6-trichlorophenyl)azo)acetate.
Claim 32
Dependent Claim
10 words
The method according to claim 11 wherein R'' is methyl.
Claim 33
Dependent Claim
10 words
The method according to claim 33 wherein R is ethoxy.
Claim 34
Dependent Claim
14 words
The method according to claim 34 wherein Y is lower-alkoxy and m is 1.
Claim 35
Dependent Claim
10 words
The method according to claim 35 wherein Y is methoxy.
Claim 36
Dependent Claim
8 words
The method according to claim 36, ethyl 2-chloro-2-((o-methoxyphenyl)azo)propionate.
Claim 37
Dependent Claim
10 words
The method according to claim 11 wherein X is fluorine.
Claim 38
Dependent Claim
10 words
The method according to claim 38 wherein Y is halogen.
Claim 39
Dependent Claim
10 words
The method according to claim 39 wherein Y is chlorine.
Claim 40
Dependent Claim
8 words
The method according to claim 40, ethyl 2-fluoro-2-((2,4,6-trichlorophenyl)azo)propionate.
Claim 41
Dependent Claim
23 words
Formulations for herbicidal use comprising an inert adjuvant and an eFfective concentration of an active ingredient comprising a 1''-formyl-1''-halobenzeneazomethane having the structural formula:
Claim 42
Dependent Claim
21 words
Formulations according to claim 42 wherein the 1''-formyl-1''-halobenzeneazomethanes are characterized by R being alkoxy, R'' being alkyl, and X being chlorine.
Claim 43
Dependent Claim
11 words
Formulations according to claim 43 wherein the 1''-formyl-1''-halobenzeneazomethanes are alkyl 2-chloro-2-((2,4,6-trichlorophenyl)azo)propionates.
Claim 44
Dependent Claim
12 words
Formulations according to claim 44 wherein the alkyl 2-chloro-2-((2,4,6-trichlorophenyl)azo)propionates is ethyl 2-chloro-2-((2,4,6-trichlorophenyl)azo)propionate.
Claim 45
Dependent Claim
12 words
Formulations according to claim 42 wherein the 1''-formyl-1''-halobenzeneazomethanes are alkyl dichloro-((Ym phenyl)azo)acetates.
Claim 46
Dependent Claim
13 words
Formulations according to claim 46 wherein the alkyl dichloro-((Ym phenyl)azo)acetates is ethyl dichloro-((2,4-dichlorophenyl)azo)acetate.
Claim 47
Dependent Claim
13 words
Formulations according to claim 46 wherein the alkyl dichloro-((Ym phenyl)azo)acetates is isopropyl dichloro-((2,4,6-trichlorophenyl)azo)acetate.
Claim 48
Dependent Claim
15 words
Formulations according to claim 42 wherein a solvent adjuvant for the active ingredient is present.
Claim 49
Dependent Claim
10 words
Formulations according to claim 49 wherein a surfactant is present.
Claim 50
Dependent Claim
13 words
Formulations according to claim 42 wherein a finely divided solid adjuvant is present.
Claim 51
Dependent Claim
10 words
Formulations according to claim 51 wherein a surfactant is present.
Claim 52
Dependent Claim
13 words
Formulations according to claim 50 wherein the solvent is not miscible with water.
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) | 1977-08-19 | 1978-02-18 | 1978-08-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1981-08-19 | 1982-02-18 | 1982-08-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1985-08-19 | 1986-02-18 | 1986-08-20 | $7700.00 | Window Closed / Lapsed |