GB1573576A - Phthalamic acids and nicotinic acids and their use as plant growth regulants - Google Patents
Phthalamic acids and nicotinic acids and their use as plant growth regulants Download PDFInfo
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- GB1573576A GB1573576A GB53127/77A GB5312777A GB1573576A GB 1573576 A GB1573576 A GB 1573576A GB 53127/77 A GB53127/77 A GB 53127/77A GB 5312777 A GB5312777 A GB 5312777A GB 1573576 A GB1573576 A GB 1573576A
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- pyridyl
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fertilizers (AREA)
Abstract
The plant growth regulators contain from 1 to 99 % by weight of an active substance of the formula: <IMAGE> or an alkali metal salt, amine salt or ammonium salt thereof. In the formula I, R, R1 and R2 have the meanings given in Patent Claim 1. To alter the development of the reproductive components of a maize plant, an effective and non-lethal amount of an active substance of the formula I is applied to the maize plant.
Description
(54) PHTHALAMIC ACIDS AND NICOTINIC ACIDS AND
THEIR USE AS PLANT GROWTH REGULANTS
(71) We, MONSANTO COMPANY, a corporation organise under the
\'*/-'--.-,..r*..Jt-:-- < 0 < Vt\.ThT < nf < < 'r < th PATENTS ACT, 1949
SPECIFICATION NO 1573576
The following amendments were allowed under Section 29 on 28 May 1981 Page I, Heading (54), after AND second occurrence insert DERIVATIVES THEREOF AND
Page 1, line 7, after and the irzserr derivatives including
Page 2, lines 5,6 and 19, after acids insert and their derivaties
Page 2, lines 8 and 13, page 9, lines 9 and 20, after defined insert provided that when R is hydrogen
and R2 is a monosubstituted pyridyl, then the substituent on the pyridyl cannot be lower alkoxy as
herein defined in the 4-position when the nitrogen atom in the ring is in the 3-position
Page 2, line 13, delete and insert ; or
Page 6, lines 25 and 32, delete acids insert compounds
Page 7, lines 8 and 9, lelete phthaiamic acids insert compounds of Formula 1 THE PATENT OFFICE 19 Bas 83461/9 provided that @@@@@@ A @@@ @ @@@ @@ @@@@@@ atom is in the 3 position.
The term"substituted phenyl"as used herein is understood to mean those radicals having the formula
wherein X and Y are defined as above.
(54) PHTHALAMIC ACIDS AND NICOTINIC ACIDS AND
THEIR USE AS PLANT GROWTH REGULANTS
(71) We, MONSANTO COMPANY, a corporation organised under the laws of the State of Delaware, United States of America, of 800 North Lindbergh
Boulevard, St. Louis, Missouri 63166, United States of America, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement :- This invention relates to phthalmic acids and nicotinic acids and the salts thereof.
Said compounds are useful as the active ingredient in plant growth regulating compositions.
More particularly, the invention relates to a method for altering the development of the reproductive components of a corn plant which comprises applying to said corn plant an effective, non-lethal amount of a compound having the formula
wherein R is hydrogen or lower alkyl ; Ri is carbon or nitrogen; R is pyridyl, substituted pyridyl as herein defined or when Ri is nitrogen, R2 may be substituted phenyl as herein defined ; and agriculturally acceptable salts thereof.
The term"substituted pyridyl"as used herein is understood to mean those radicals having the formulae
wherein X is selected from hydrogen, halogen, trifluoromethyl, lower alkyl and lower alkoxy and Y is selected from halogen, trifluoromethyl, lower alkyl and lower alkoxy ; provided that neither X nor Y may be chlorine in the 4 position when the nitrogen atom is in the 3 position.
The term"substituted phenyl"as used herein is understood to mean those radicals having the formula
wherein X and Y are defined as above.
As used herein, the term"agriculturally acceptable salts"includes alkali metal, substituted amine, such as isopropylamine and triethylamine and ammonium salts.
The terms"lower alkyl"and"lower alkoxy"are understood to include those alkyl and alkoxy radicals having from one to four carbon atoms inclusive.
Some of the phthalamic acids are novel and they form an aspect of the present invention. The novel phthalamic acids are compounds having the formula
wherein R is hydrogen or lower alkyl ; R2 is substituted pyridyl as herein defined or agriculturally acceptable salts thereof.
Another aspect of the present invention is a plant growth regulating composition which comprises from 1 to 99 parts by weight of a compound having the formula
wherein R is hydrogen or lower alkyl ; Rz is substituted pyridyl as herein defined and an agriculturally acceptable salt thereof ; the remaining parts being compose of one or more suitable carriers, diluentsånd/or adjuvants.
The phthalamic acids may be prepared by adding a stoichiometric equivalent of the appropriate aminopyridine to a slurry containing phthalic anhydride and chloroform. After stirring at room temperature, the precipitate may be filtered and air-dried. To illustrate the preparation of the novel phthalamic acids, the following
Examples are presented. In the Examples the percentages mentioned are expressed in terms of weight.
Example 1.
To a stirred slurry containing 0.1 moles of phthalic anhydride and 100 ml. of chloroform, 0.1 moles of 3-amino-2-chloropyridine was added in one portion.
The reaction mixture was stirred for 24 hours. The precipitate was filtered, air-dried and identified as N- (2-chloro-3-pyridyl) phthalamic acid having a melting point of 203 C. (% yield=87) Anal. Calc'd. Cl. 12.81 ; N, 10.12
Found Cl, 12.94; N, 10.37.
In accordance with the procedure of Example 1, the following compounds have been prepared.
Analysis
Example Compound Calculated Found # 2 N-(6-methoxy-3-pyridyl)phthalamic acid C, 61.80; H, 4,44, N, 10.30 C, 61.94, H, 4.42; N, 10.26 3 N-(5-bromo-2-pyridyl)phthalamic acid N, 8.72; Br, 24.88 N, 8.69; Br, 24.75 4 N-(4,6-dimethyl-1-2-pyridyl)phthalamic acid C, 66.65; H, 5.22; N, 10.36 C, 66,53; H, 5.28; N, 10.35 The soduim salt of the novel phthalamic acids may be prepared by stirring for one hour a stoichiometrically equivalent amount of 50% aqueous NaOH and 400 ml. of water for a 0.1 mole reaction. In accordance with this procedure, the following compounds have been prepared.
Example Compound 5 Soduim salt of N-(5-chloro-2-pyridyl)phthalamic acid 6 Soduim salt of N-(2-chloro-3-pyridyl)phthalamic acid
Ammonium and substituted amine salts may be prepared in accordance with the following examples.
Example 7.
To a stirred slurry of 0.1 moles of N - (2 - chloro - 3 - pyridyl)phthalamic acid and 500 ml of diethyl ether, 0.11 moles of isopropylamine, to form the isopropylamine salt, was added in one portion. After stirring at 25--30 C. for 24 hours,a solid was collected by filtration and air-dried. The product, m.p. 147--148 C., was obtained in 100% yield.
Anal. Calc'd. C, 57.23; H, 5.40; Cl, 10.56; N, 12.61
Found C, 57.68; H, 5.45; Cl, 10.71; N, 12.59.
Example 8.
The procedure of Example 7 was followed to prepare the isopropylamine salt of
N - (5 - bromo - 2 - pyridyl)phthalamic acid, m.p. 145--146 C., in 87% yield.
Anal Calc'd C, 50.54; H, 4.77; N, 11.05
Found C, 50.42; H, 4.73; N, 10.99.
The nicotinic acids of the present invention may be prepared by adding 0.1 moles of the appropriate substituted aniline or aminochloropyridine to a slurry of 0.1 moles of 2,3 - pyridinecarboxylic acid anhydride and 100 ml of chloroform. After stirring at 25--30 C. for 24 hours, the solids are collected by filtration and air-dried at 25-30 C. The compounds of Examples 9--16, summarized by Table I below, were prepared in accordance with the above procedure.
TABLE I
Percent Percent C Percent H Percent N Example R, m. p. C. Yield Calc'd. Found Calc'd. Found Calc'd. Found OCH3 9 178-9 95 59.60 59.62 4.67 4.69 9. 27 9, 31 OCH3 CF3 10 4 111-2 (b) 90 54.20 54.37 2.92 3. 07-
Cl 11 C F3 139-9 (e) 73 48.79 48.69 2.34 2.31 8.13 8.18 CF CF3 12 174-5 (b) 99 47.63 47.89 2.13 2.10 7.41 7.30 CF3 3 13 -C ! 150-1 94 51.91 51.47 2.90 3.02 15.13 15.47 , li. i. a, l bl'aldl MGloia, "ii. nlkllr : avlw. n. niH :. ; rk. lul TABLE I (continued)
Percent Percent C Percent H Percent N Example R2 m. p. C. Yield Calc'd. Found Calc'd. Found Calc'd. Found CF3 14 ci 184-5 (d) 96 48.79 48.68 2.34 2.25 8.13 8.04 15 54. 08 2.92 2.88 9. 03 9.18 U 16 oCF3 182-3 95 54. 07 2. 92 2. 89- (a) Recrystallization from methyl alcohol.
(b) Recrystallization from heptane/isopropyl alcohol.
(c) Recrystallization from NaOII/HCI.
(b) Recrystallization from isopropyl alcohol.
Esters may be prepared as follows.
Example 17.
To a stirred slurry containing 27.7 grams (0. 1 moles) of N - (2 - chloro - 3- pyridyl) phthalamic acid and 300 ml. of methyl alcohol, 71 grams (0.5 moles) of boron trifluoride etherate [(C2Hs) 2O BF3] is added in one portion. An exothermic reaction set in causing a temperature rise from 21 to 33 C. The stirred mixture is heated at reflux for 24 hours. After cooling to-10'C., 1000-ml. of a 10% aqueous sodium bicarbonate solution is added slowly at-10 to 0 C. After stirring at 0 to 10 C. for 30 minutes, the solid is collected by filtration, tvshed with water until neutral and air-dried at 2530 C. The product, which is the methyl ester of N- (2chloro-3-pyridyl) phthalamic acid, m. p. 110-112 C., is obtained in 76% yield.
After two recrystallizations from heptane/isopropyl alcohol, it melted at 122-124 C.
Anal. Calc'd. for Cl4HIlClNzOq : C, 57. 84; H, 3.81 ; Cl, 12.20; N, 9.64.
Found: C, 57. 88; H, 3.57; Cl, I2. 45 ; N, 9.41.
The compounds represented by Formula I above have been-found to be effective in altering the development of both the male (tassel) and female (ear) reproductive components of corn plants. As used herein, the alteration of the"development of the reproductive component"of the corn plant is understood to mean the modification of the normal sequential development to said component to maturity. Such modifications are most readily observed as inhibition of tassel growth, inhibition of lateral tassel branches, alteration in ear numbers, shape, position, kernel numbers, speed of silking, etc.
The invention contemplates the alteration of the development of the reproductive- components of healthy corn plants by applying an effective, non-lethal amount of the acids of Formula I to said corn plant before or during the early stages of the development of said reproductive component referred to herein as reproductive differentiation.
As a result of such application, tassel size can be reduced or eliminated, thus reducing or eliminating the labor required by hybrid seed corn producers to manually detassel said corn plants. Additionally, the amount of seed per unit area of land may be increased by applying an effective amount of the active ingredient before or during the early stages of the development of said ear.
As used herein, the term"active ingredient"refers to the acids of Formula I.
In accordance with the novel aspects of the present invention, compounds 1-16 were tested in accordance with the following procedure.
Example A.
A-619 variety com plants were grown and thinned to obtain a uniform population. All weak or late plants were removed before chemical application. The active ingredient was formulated by adding 50 or 100 mg. of the active ingredient to 7.5 ml. of acetone and 7.5 ml. of water. 0.25% Tween 20 was added as a surfactant. Utilizing a Devilbiss 152 sprayer, the corn plants were sprayed during the early stages of reproductive differentiation at a rate of 10 mg. per plant or 20 mg. per plant.
(Devilbiss is a registered trade mark.)
Results were analyzed by comparing the treated plants to control plants which were not chemically treated. Chemicals were considered to be active in altering the reproductive development of the corn plant if treatment resulted in an inhibition of at least 25 percent of the lateral tassel formation when compare to the control plants.
In accordance with the above procedure, compounds I, 2, 3, 6 and 9-11 were found to be effective in inhibiting from 50 to 74 percent of the lateral tassel development. Compounds 3,7,8 and 12-16 were found to be effective in inhibiting from 25 to 49 percent of the lateral tassel development. In addition, flowering was inhibited as illustrated in Table II.
TABLE II
cm. of
Compound Flowers
Control 224 1 67 3 132
4 75
Example B.
In another test, N- (2-chloro-3-pyridyl) phthalamic acid was applied to corn plants as a formulation described above. Responses noted included alteration of ear height, increased speed of silking and partial sterility. Table III illustrates the responses noted.
TABLE III
Rate of Treatment Ear Percent
kilos/hectare Height of Male
Day g (a) Day 12 (a) Day 15 (a) (cS Sterility
0 0 0 48 0
1.12 1.12 0 73 80 1. 12 0 1.12 54 88 1. 12 0.56 0 57 75
1.12 0 0.56 52 89
0.56 1. 12 0 60 68
0.56 0 1.12 48 95
0.56 0.56 0 55 74
0.56 0 0.56 48 88 (a) from seedling emergence.
As exemplified above, the invention contemplates the application of the phthalamic acids before or during the early stages of the reproductive differentiation. Reproductive differentiation occurs at different times depending upon the variety of corn plant as well as environmental factors. For example, male reproductive differentiation of Gaspe corn begins during kernel formation while reproduction differentiation of A-619 corn begins within the first 8 to 12 days after seedling emergence. The determination of when reproductive differentiation occurs is within the skill of the art. By way of example and for purposes of illustration only, applications for most varieties used in the Midwest of the United States ranging from 3 to 25 days after seedling emergence are desirable. Varieties used in foreign countries may require applications ranging from 1 to 40 days from seedling emergence. The following examples illustrates that for A-619 variety corn, applications between 7 to 12 days after seedling emergence are preferred.
Example C.
Corn, A--619 variety, was planted is plots at a rate of 64,000 plants per hectare.
@@@ @@@@@ @ @@ @@ a formulation consisting of compound 6,50 percent acetone, 0.25 percent Tween 20 and a sufficient amount of water such that said formulation was applied at a rate of 320 liters per hectare. Tween is a registered trade mark. Some applications were made early, on or before 12 days after seedling emergence. Other applications were made late, after 12 days from seedling emergence. After harvest, the yields of the treated plants were compared to those of the untreated control plants. Table IV illustrates the results of this test.
TABLE IV Grams/Plot Early Late
Control Yields Application Application
1300
2060
1940 2940
1650 1540 1740 1680
1700 1740 1720
1910 2170 1660
1810 2430 1390
1850 2230 1480
1770 1730 1130
Mean 1773 2057 1476
In the practice of the invention, the active ingredient can be used alone or in combination with a material referred to in the art as an adjuvant in either liquid or solid form. To prepare plant growth regulating compositions, the active ingredient is admixed with an adjuvant including diluents, extenders, carriers and conditioning agents to provide compositions in the form of finely-divided particulate solids, granules, pellets, wettable powders, dusts, solutions and aqueous dispersions or emulsions. Thus, the active ingredient can be used with an adjuvant such as a finely-divided particulate solid, a solvent liquid of organic origin, water, a wetting agent, dispersing agent or emulsifying agent or any suitable combination of ~ ~ ~ Illustrative finely-divided solid carriers and extenders which are useful in plant growth regulating compositions of this invention include the talcs, clays, pumice, silica, diatomaceous earth, quartz, Fullers earth, sulfur, powdered cork, powdered wood, walnut flour, chalk, tobacco dust and charcoal. Typical liquid diluents include
Stoddard solvent, acetone, alcohols, glycols, ethyl acetate and benzene. The plant growth regulating compositions of this invention, particularly liquids and wettable powders, usually contain one or more surface-active agents in amounts sumcient to render a given composition readily dispersible in water or in oil. The term"surfaceactive agent"is understood to include wetting agents, dispersing agents, suspending agents and emulsifying agents. Such surface-active agents are well known and reference is made to U. S. Patent No. 2,547,724, Columns 3 and 4, for detailed examples of the same.
Generally, the active ingredients are applied in the form of a composition containing one or more adjuvants which aid in the application of a uniform distribution of the active ingredient. The application of liquid and particulate solid compositions of the active ingredient can be carried out by conventional techniques utilizing, for example, spreaders, power dusters, boom and hand sprayers and spray dusters. The composition can also be applied from airplanes as a dust or spray.
Compositions of this invention generally contain from 1 to 99 parts active ingredient, about 1 to 50 parts surface-active agent and 4 to 94 parts solvents, all parts being by weight based on the total weight of the composition.
In selecting the appropriate rate of application of the active ingredient, it will be recognized that percise rates will also be dependent upon the mode of application, art. While a rate of 0.056 to 5. 6 kilos per hectare is preferred, higher rates of up to 56 kilos per hectare may be used, depending upon the factors noted above.
This invention, however, does not contemplate the use of phytotoxic rates which exert a herbicidal effect. In addition, it will be recognized that single or multiple applications may be used to exert the desired response.
Claims (19)
1. A compound having the formula
wherein R is hydrogen or lower alkyl ; R is substituted pyridyl as herein defined or an agriculturally acceptable salt thereof.
2. A compound according to Claim 1 which is N- (2-chloro-3-pyridyl)- phthalamic acid.
3. A compound according to Claim 1 which is the sodium salt of N- (2-chloro3-pyridyl) phthalamic acid.
4. A compound according to Claim 1 that has been specifically named in any of the Examples.
5. A plant growth regulating composition which comprises from 1 to 99 parts by weight of a compound having the formula
wherein R is hydrogen or lower alkyl ; R2 is substituted pyridyl as herein defined ; or an agriculturally acceptable salt thereof ; the remaining parts being composed of one or more suitable carriers, diluents and/or adjuvants.
6. A composition according to Claim 5 wherein said compound is N- (2-chloro3-pyridyl) phthalamic acid.
7. A composition according to Claim 5 wherein said compound is the sodium salt of N- (2-chloro-3-pyridyl) phthalamic acid.
8. A composition according to any of Claims 5 to 7 which comprises a surface active agent.
9. A composition according to any of Claims 5 to 8 which is in the form of a finely divided particulate solid, a granule, a pellet, a wettable powder, a dust, a solution, an aqueous dispersion or an aqueous emulsion.
10. A method for altering the development of the reproductive components of a com plant which comprises applying to said com plant an effective, non-lethal amount of a compound of the formula
wherein R is hydrogen or lower alkyl ; Rl is carbon or nitrogen ; R2 is pyridyl, substituted pyridyl as herein defined or when Rl is nitrogen, R2 may be pyridyl, substituted pyridyl as herein defined or substituted phenyl as herein defined ; or an agriculturally acceptable salt thereof.
11. A method according to Claim 10 wherein said compound has the formula'"
wherein R is pyridyl or substituted pyridyl.
12. A method according to Claim 11 wherein R is substituted pyridyl.
13. A method according to Claim 11 wherein said compound is N- (2-chloro3-pyridyl) phthalamic acid.
14. A method according to Claim 11 wherein said compound is the sodium salt of N- (2-chloro-3-pyridyl) phthalamic acid.
15. A method according to Claim 10 wherein said compound has the formula
wherein R is pyridyl, substituted pyridyl or substituted phenyl.
16. A method according to any of Claims 10 to 15 wherein the said compound is applied at a rate of from 0.056 to 5. 6 kilos per hectare.
17. A method according to any of Claims 10 to 15 wherein the said compound is applied from 1 to 40 days from seedling emergence.
18. A method according to Claim 17 wherein the said compound is applied from 7 to 12 days after seedling emergence.
19. A method according to Claim 18 wherein said compound is applied from 8 to 12 days after seedling emergence.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75326076A | 1976-12-22 | 1976-12-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1573576A true GB1573576A (en) | 1980-08-28 |
Family
ID=25029880
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB53127/77A Expired GB1573576A (en) | 1976-12-22 | 1977-12-21 | Phthalamic acids and nicotinic acids and their use as plant growth regulants |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS5379871A (en) |
| AR (1) | AR220111A1 (en) |
| AU (1) | AU516014B2 (en) |
| BE (1) | BE862113A (en) |
| CA (1) | CA1112645A (en) |
| CH (1) | CH632997A5 (en) |
| CS (1) | CS196411B2 (en) |
| DD (1) | DD133884A5 (en) |
| DE (1) | DE2757111A1 (en) |
| DK (1) | DK571377A (en) |
| FR (2) | FR2387960A1 (en) |
| GB (1) | GB1573576A (en) |
| HU (1) | HU179545B (en) |
| IL (1) | IL53671A (en) |
| IT (1) | IT1090352B (en) |
| MY (1) | MY8200169A (en) |
| NL (1) | NL7714092A (en) |
| PH (1) | PH16343A (en) |
| PL (1) | PL106999B1 (en) |
| SU (1) | SU942573A3 (en) |
| ZA (1) | ZA777589B (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0041623A2 (en) * | 1980-06-02 | 1981-12-16 | American Cyanamid Company | Substituted imidazolinyl nicotine acids, esters and salts and use thereof as herbicidal agents |
| EP0144595A1 (en) * | 1983-11-07 | 1985-06-19 | American Cyanamid Company | Preparation of 2-carbamoyl nicotinic and 3-quinoline carboxylic acids |
| US4556414A (en) * | 1981-06-25 | 1985-12-03 | Rhone-Poulenc Agrochimie | Herbicidal dihydropyridine amides |
| EP0184027A2 (en) * | 1984-12-03 | 1986-06-11 | American Cyanamid Company | Preparation of substituted and unsubstituted 2-carbamoyl nicotinic and 3-quinolinecarboxylic acids |
| WO2001055115A1 (en) * | 2000-01-27 | 2001-08-02 | Cytovia, Inc. | Substituted nicotinamides and analogs as activators of caspases and inducers of apoptosis and the use thereof |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59118750A (en) * | 1982-12-27 | 1984-07-09 | Eisai Co Ltd | Carboxylic acid amide compound and its derivative |
| RU2629990C1 (en) * | 2016-05-19 | 2017-09-05 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Государственный аграрный университет Северного Зауралья" (ФГБОУ ВО ГАУ Северного Зауралья) | Method for inhibiting seed germination of grain crops |
| JP6768631B2 (en) | 2017-12-20 | 2020-10-14 | コベストロ、ドイチュラント、アクチエンゲゼルシャフトＣｏｖｅｓｔｒｏ Ｄｅｕｔｓｃｈｌａｎｄ Ａｇ | Flame-retardant polyisocyanurate foam |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR929965A (en) * | 1945-09-18 | 1948-01-13 | Pyridium Corp | Process for obtaining pyridine phthalamidic acid compounds and its salts |
| DE1642224B2 (en) * | 1967-04-28 | 1976-04-29 | Basf Ag, 6700 Ludwigshafen | USE OF SUBSTITUTED BENZOIC ANILIDES FOR CONTROL OF FUNGI FROM THE CLASS OF BASIDIOMYCETS |
| CH489993A (en) * | 1967-12-19 | 1970-05-15 | Ciba Geigy | Plant growth regulating and phytocidal agent |
| FR2059977A1 (en) * | 1969-08-14 | 1971-06-11 | Socibre |
-
1977
- 1977-12-20 NL NL7714092A patent/NL7714092A/en unknown
- 1977-12-21 HU HU77MO998A patent/HU179545B/en unknown
- 1977-12-21 GB GB53127/77A patent/GB1573576A/en not_active Expired
- 1977-12-21 JP JP15501477A patent/JPS5379871A/en active Granted
- 1977-12-21 SU SU772556503A patent/SU942573A3/en active
- 1977-12-21 DE DE19772757111 patent/DE2757111A1/en not_active Withdrawn
- 1977-12-21 IT IT31043/77A patent/IT1090352B/en active
- 1977-12-21 CS CS778654A patent/CS196411B2/en unknown
- 1977-12-21 CA CA293,560A patent/CA1112645A/en not_active Expired
- 1977-12-21 IL IL53671A patent/IL53671A/en unknown
- 1977-12-21 AR AR270438A patent/AR220111A1/en active
- 1977-12-21 DK DK571377A patent/DK571377A/en not_active Application Discontinuation
- 1977-12-21 FR FR7738669A patent/FR2387960A1/en active Granted
- 1977-12-21 PL PL1977203191A patent/PL106999B1/en unknown
- 1977-12-21 DD DD77202844A patent/DD133884A5/en unknown
- 1977-12-21 PH PH20583A patent/PH16343A/en unknown
- 1977-12-21 ZA ZA00777589A patent/ZA777589B/en unknown
- 1977-12-21 CH CH1579177A patent/CH632997A5/en not_active IP Right Cessation
- 1977-12-21 BE BE183675A patent/BE862113A/en not_active IP Right Cessation
- 1977-12-22 AU AU31877/77A patent/AU516014B2/en not_active Expired
-
1978
- 1978-05-23 FR FR7815339A patent/FR2381029A1/en active Granted
-
1982
- 1982-12-30 MY MY169/82A patent/MY8200169A/en unknown
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0041623A2 (en) * | 1980-06-02 | 1981-12-16 | American Cyanamid Company | Substituted imidazolinyl nicotine acids, esters and salts and use thereof as herbicidal agents |
| EP0041623A3 (en) * | 1980-06-02 | 1982-09-22 | American Cyanamid Company | Substituted imidazolinyl nicotine acids, esters and salts and use thereof as herbicidal agents |
| US4556414A (en) * | 1981-06-25 | 1985-12-03 | Rhone-Poulenc Agrochimie | Herbicidal dihydropyridine amides |
| EP0144595A1 (en) * | 1983-11-07 | 1985-06-19 | American Cyanamid Company | Preparation of 2-carbamoyl nicotinic and 3-quinoline carboxylic acids |
| EP0184027A2 (en) * | 1984-12-03 | 1986-06-11 | American Cyanamid Company | Preparation of substituted and unsubstituted 2-carbamoyl nicotinic and 3-quinolinecarboxylic acids |
| EP0184027B1 (en) * | 1984-12-03 | 1990-02-07 | American Cyanamid Company | Preparation of substituted and unsubstituted 2-carbamoyl nicotinic and 3-quinolinecarboxylic acids |
| WO2001055115A1 (en) * | 2000-01-27 | 2001-08-02 | Cytovia, Inc. | Substituted nicotinamides and analogs as activators of caspases and inducers of apoptosis and the use thereof |
| US6794397B2 (en) | 2000-01-27 | 2004-09-21 | Cytovia, Inc. | Substituted nicotinamides and analogs as activators of caspases and inducers of apoptosis and the use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CS196411B2 (en) | 1980-03-31 |
| DK571377A (en) | 1978-06-23 |
| IT1090352B (en) | 1985-06-26 |
| HU179545B (en) | 1982-11-29 |
| IL53671A (en) | 1982-05-31 |
| DD133884A5 (en) | 1979-01-31 |
| PL106999B1 (en) | 1980-01-31 |
| FR2381029A1 (en) | 1978-09-15 |
| PH16343A (en) | 1983-09-05 |
| NL7714092A (en) | 1978-06-26 |
| AU3187777A (en) | 1979-06-28 |
| JPS6134421B2 (en) | 1986-08-07 |
| MY8200169A (en) | 1982-12-31 |
| CA1112645A (en) | 1981-11-17 |
| BE862113A (en) | 1978-06-21 |
| FR2381029B1 (en) | 1982-07-23 |
| AU516014B2 (en) | 1981-05-14 |
| SU942573A3 (en) | 1982-07-07 |
| DE2757111A1 (en) | 1978-07-06 |
| IL53671A0 (en) | 1978-03-10 |
| PL203191A1 (en) | 1978-07-03 |
| ZA777589B (en) | 1978-10-25 |
| AR220111A1 (en) | 1980-10-15 |
| CH632997A5 (en) | 1982-11-15 |
| FR2387960B1 (en) | 1982-06-25 |
| FR2387960A1 (en) | 1978-11-17 |
| JPS5379871A (en) | 1978-07-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| 429A | Application made for amendment of specification (sect. 29/1949) | ||
| 429H | Application (made) for amendment of specification now open to opposition (sect. 29/1949) | ||
| 429D | Case decided by the comptroller ** specification amended (sect. 29/1949) | ||
| SP | Amendment (slips) printed | ||
| PCNP | Patent ceased through non-payment of renewal fee |