US3947263A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Plant growth regulants
Assignee: Uniroyal Ltd Canada
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Filing: 1974-07-29
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Granted: 1976-03-30
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Expires: 1994-07-29
Abstract
Abstract Plant growth regulant effects, such as dwarfing, cessation of terminal growth, increased flower set, increased fruit and pod set, fruiting body abortion, twisting and epinastic responses, etc., may be accomplished on crops such as soybeans, cotton, etc., by application of certain 2-(1,3,4-oxadiazol-2-yl) or 2-(2-oxazolyl) or 2-(1,3,4-thiadiazol-2-yl)benzoic acids, salts and esters, having the formula ##SPC1## Where X is nitrogen or C--R" (R" being hydrogen or methyl), Z is oxygen or sulfur when X is nitrogen, Z is oxygen when X is C--R", R is phenyl or various substituents, and R' is hydrogen or various substituents. An example is 2-(5-phenyl-1,3,4-oxadiazol-2-yl)benzoic acid. The compounds where X is nitrogen and Z is sulfur are new compounds, e.g., 2-(5-phenyl-1,3,4-thiadiazol-2-yl)benzoic acid.
Inventors
- 👤 Walter G. Brouwer
- 👤 Edwin J. MacPherson
- 👤 Ronald B. Ames
- 👤 Robert W. Neidermyer
- 👤 Charles E. Crittendon
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 21:08
CPC Classifications
C; C07; C07D; C07D285/00; C07D285/01; C07D285/02; C07D285/04; C07D285/12
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
157 words
A method of retarding the growth of plants comprising applying to plants, in a non-herbicidal amount effective to retard the growth of the plants, a chemical which is a 2-(1,3,4-oxadiazol-2-yl) [, a 2-(2-oxazolyl) or a 2-(1,3,4-thiadiazol-2-yl)] benzoic acid, salt, or ester of the formula ##SPC6## where X is nitrogen [or C-R"], Z is oxygen [or sulfur when X is nitrogen, Z is oxygen when X is C-R"], R is the group ##SPC7## where the Y's are the same or different and are selected from the group consisting of hydrogen, halogen, nitro, lower alkyl and lower alkoxy, R' is selected from the group consisting of hydrogen, a moiety which forms an alkali metal, a polyvalent metal, an ammonium, alkyl- or hydroxyalkylammonium salt with said acid, and a moiety which forms an aliphatic or cycloaliphatic hydrocarbyl or epoxy lower alkyl ester with said acid wherein the alkyl, hydroxyalkyl, aliphatic or cycloaliphatic moieties may contain up to 12 carbon atoms.
Claim 2
Independent Claim
157 words
A method of retarding the growth of plants comprising applying to plants, in a non-herbicidal amount effective to retard the growth of the plants, a chemical which is a 2-(1,3,4-oxadiazol-2-yl) [, a 2-(2-oxazolyl) or a 2-(1,3,4-thiadiazol-2-yl)] benzoic acid, salt, or ester of the formula ##SPC6## where X is nitrogen [or C-R"], Z is oxygen [or sulfur when X is nitrogen, Z is oxygen when X is C-R"], R is the group ##SPC7## where the Y's are the same or different and are selected from the group consisting of hydrogen, halogen, nitro, lower alkyl and lower alkoxy, R' is selected from the group consisting of hydrogen, a moiety which forms an alkali metal, a polyvalent metal, an ammonium, alkyl- or hydroxyalkylammonium salt with said acid, and a moiety which forms an aliphatic or cycloaliphatic hydrocarbyl or epoxy lower alkyl ester with said acid wherein the alkyl, hydroxyalkyl, aliphatic or cycloaliphatic moieties may contain up to 12 carbon atoms.
Claim 3
Independent Claim
54 words
A method of retarding the growth of plants comprising applying to the plants, in a non-herbicidal amount effective to retard the growth of the plants, a chemical selected from the group consisting of 2-(5-phenyl-1,3,4-oxadiazol-2-yl)benzoic acid, 2-[5-(2-tolyl)-1,3,4-oxadiazol-2-yl]benzoic acid, 2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl]benzoic acid, 2-[5-(2-chlorophenyl)-1,3,4-oxadiazol-2-yl]benzoic acid, 2-[5-(3-chlorophenyl)-1,3,4-oxadiazol-2-yl]benzoic acid, 2-[5-(2-methoxyphenyl)-1,3,4-oxadiazol-2-yl]benzoic acid, propargyl 2-(5-phenyl-1,3,4-oxadiazol-2-yl)benzoate, butyl 2-(5-phenyl-1,3,4-oxadiazol-2-yl)benzoate, 2-[5-(3-nitrophenyl)-1,3,4-oxadiazol-2-yl]benzoic acid, and methyl 2-(5-phenyl-1,3,4-oxadiazol-2-yl)benzoate.
Claim 4
Independent Claim
54 words
A method of retarding the growth of plants comprising applying to the plants, in a non-herbicidal amount effective to retard the growth of the plants, a chemical selected from the group consisting of 2-(5-phenyl-1,3,4-oxadiazol-2-yl)benzoic acid, 2-[5-(2-tolyl)-1,3,4-oxadiazol-2-yl]benzoic acid, 2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl]benzoic acid, 2-[5-(2-chlorophenyl)-1,3,4-oxadiazol-2-yl]benzoic acid, 2-[5-(3-chlorophenyl)-1,3,4-oxadiazol-2-yl]benzoic acid, 2-[5-(2-methoxyphenyl)-1,3,4-oxadiazol-2-yl]benzoic acid, propargyl 2-(5-phenyl-1,3,4-oxadiazol-2-yl)benzoate, butyl 2-(5-phenyl-1,3,4-oxadiazol-2-yl)benzoate, 2-[5-(3-nitrophenyl)-1,3,4-oxadiazol-2-yl]benzoic acid, and methyl 2-(5-phenyl-1,3,4-oxadiazol-2-yl)benzoate.
Claim 5
Dependent Claim
14 words
A method as in claim 2 in which the said chemical is 2-(5-phenyl-1,3,4-oxadiazol-2-yl]benzoic acid.
Claim 6
Dependent Claim
14 words
A method as in claim 2 in which the said chemical is 2-[5-(2-tolyl)-1,3,4-oxadiazol-2-yl]benzoic acid.
Claim 7
Dependent Claim
14 words
A method as in claim 2 in which the said chemical is 2-[5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl]benzoic acid.
Claim 8
Dependent Claim
14 words
A method as in claim 2 in which the said chemical is 2-[5-(2-chlorophenyl)-1,3,4-oxadiazol-2-yl]benzoic acid.
Claim 9
Dependent Claim
14 words
A method as in claim 2 in which the said chemical is 2-[5-(3-chlorophenyl)-1,3,4-oxadiazol-2-yl]benzoic acid.
Claim 10
Dependent Claim
14 words
A method as in claim 2 in which the said chemical is 2-[5-(2-methoxyphenyl)-1,3,4-oxadiazol-2-yl]benzoic acid.
Claim 11
Dependent Claim
14 words
A method as in claim 2 in which the said chemical is propargyl 2-(5-phenyl-1,3,4-oxadiazol-2-yl)benzoate.
Claim 12
Dependent Claim
15 words
A method as in claim 2 in which the said chemical is butyl 2-(5-phenyl-1,3,4-oxadiazol-2-yl) benzoate.
Claim 13
Dependent Claim
14 words
A method as in claim 2 in which the said chemical is 2-[5-(3-nitrophenyl)-1,3,4-oxadiazol-2-yl]benzoic acid.
Claim 14
Dependent Claim
14 words
A method as in claim 2 in which the said chemical is methyl 2-(5-phenyl-1,3,4-oxadiazol-2-yl)-benzoate.
Claim 15
Dependent Claim
13 words
A method as in claim 2 in which the plants are cotton plants.
Claim 16
Dependent Claim
13 words
A method as in claim 2 in which the plants are soybean plants.
Claim 17
Dependent Claim
13 words
A method as in claim 2 in which the plants are sugar-producing plants.
Claim 18
Dependent Claim
13 words
A method as in claim 2 in which the plants are peanut plants.
Claim 19
Dependent Claim
14 words
A method as in claim 2 in which the plants are small grain plants.
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) | 1979-03-30 | 1979-09-29 | 1980-03-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-03-30 | 1983-09-29 | 1984-03-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-03-30 | 1987-09-29 | 1988-03-30 | $7700.00 | Window Closed / Lapsed |