JPS6134421B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention is based on the formula [In the formula, R is hydrogen or lower alkyl, and R ₁ is of the formula

【formula】

[expression] or

[Formula] (wherein, X is selected from the group consisting of hydrogen, halogen, lower alkyl and lower alkoxy,
Y is selected from the group consisting of halogen, lower alkyl and lower alkoxy, provided that if the nitrogen atom is present at the 3rd position with respect to the bond in the above formula, then X or Y is the chlorine at the 4th position with the same meaning. and if the nitrogen atom is present in the 3-position with respect to the bond in the above formula and X is hydrogen, then Y cannot be a lower alkoxy group in the 4-position in the same sense). Substituted pyridyl] and their salts. The compounds described above are useful as active ingredients in compositions that regulate plant growth. As used herein, the term "agriculturally acceptable salts" includes alkali metal, substituted amine salts and ammonium salts such as isopropylamine and triethylamine. The terms "lower alkyl" and "lower alkoxy" are understood to include alkyl and alkoxy groups having 1 to 4 carbon atoms. The above phthalamic acids can be prepared by adding stoichiometrically equivalent amounts of the appropriate aminopyridine to a slurry of phthalic anhydride and chloroform. After stirring at room temperature, filter the precipitate and air dry. The production of novel phthalamic acid will be explained below with reference to Examples. Example 1 0.1 mol of phthalic anhydride and 100 ml of chloroform
3-amino-2 into a stirred slurry containing
- Add 0.1 mol of chloropyridine all at once. The reaction mixture is stirred for 24 hours. Filter the precipitate and air dry. It is N-(2-chloro-3-pyridyl)phthalamic acid (yield 87%) with m.p 203℃
is identified as . The elemental analysis values are as follows. ClN Calculated value: 12.81 10.12 Actual value: 12.94 10.37 Examples 2 to 5 The following compounds are produced by the operation of Example 1.

[Table] The above novel sodium salt of phthalamic acid is
50% of stoichiometric equivalent for 0.1 mole of reaction
It can be prepared by stirring aqueous NaOH and 400 ml of water for 1 hour. The following compound is produced by this operation.

TABLE Ammonium salts and substituted amine salts can be prepared according to the following examples. Example 6 To a stirred slurry of 0.1 mole of N-(2-chloro-3-pyridyl)phthalamic acid and 500 ml of ethyl ether is added 0.11 mole of isopropylamine in one portion to form the isopropylamine salt. After stirring at 25-30°C for 24 hours, remove the solids and air dry. The product with mp 147-148°C is obtained in 100% yield. The elemental analysis results are as follows. C H Cl N Calculated value: 57.23 5.40 10.56 12.61 Actual value: 57.68 5.45 10.71 12.59 Example 7 Following the procedure of Example 5, N-(5-bromo-2-
An isopropylamine salt of pyridyl)phthalamic acid is produced. mp145-146℃. Yield 87%.
The elemental analysis results are as follows. C H N calculated value: 50.54 4.77 11.05 Actual value: 50.42 4.73 10.99 The ester can be produced as follows. Example 8 27.7 g (0.1 mol) of N-(2-chloro-3-pyridyl)phthalamic acid and methyl alcohol
71 g (0.5 mol) of boron trifluoride etherate [(C ₂ H ₅ ) ₂ O.BF ₃ ] are added at once to the stirred slurry containing 300 ml. An exothermic reaction occurs and the temperature is 21
℃ to 33℃. This stirred mixture
Heat under reflux for 24 hours. After cooling to -10°C, add 1000ml of 10% aqueous sodium bicarbonate solution to -10°~0°C.
Add gradually. After stirring for 30 minutes at 0° to 10°C, remove the solids, wash with water until neutral, and mix for 25 to 30 minutes.
Air dry at 30℃. N-(chloro-3-pyridyl)
The product, which is the methyl ester of phthalamic acid (mp 110-112°C), is obtained in a yield of 76%. After two recrystallizations from heptane/isopropyl alcohol it melts at 122-124°C.
The elemental analysis results as C ₁₄ H ₁₁ ClN ₂ O ₃ are as follows. C H Cl N Calculated: 57.84 3.81 12.20 9.64 Actual: 57.88 3.57 12.45 9.41 The compound represented by the above formula is effective in modifying the development of both the male (hanger) and female (ear) reproductive parts of the corn plant. It was found to be effective. As used herein, alteration of the "development of reproductive parts" of a corn plant means
It is understood to mean a modification of the normal sequential development of the above-mentioned organs until they reach maturity. Such changes are often easily observed as inhibition of flower growth, suppression of lateral flower branches, changes in panicle number, morphology, position, grain number, panicle silking rate, etc. The present invention provides a method for producing corn plants by applying an effective non-lethal amount of an acid of the formula to a healthy corn plant before or during the early stages of development of the reproductive parts described herein as reproductive differentiation. , contemplates altering the development of the reproductive parts of the above-mentioned corn plants. Such applications can result in a reduction in the size of the dandelion or the removal of the dandelion, thus making it easier for the replacement seed corn grower to remove the dandelion by hand from the corn plants mentioned above. The work required can be reduced or eliminated. Furthermore, by applying an effective amount of the active ingredient before or during the early stages of panicle development as described above, the amount of seeds per unit area of land can be increased. The term "active ingredient" as used herein refers to an acid of the formula. According to the novel aspect of the present invention, compounds 1-7 are tested by the following procedure. Test Example A A corn plant variety A-619 is grown and sown to obtain a uniformly grown population. All soft or slow-growing plants are removed prior to compound application. Active ingredient 50mg or 100
Formulate the active ingredient by adding mg to 7.5 ml of acetone and 7.5 ml of water. Add 0.25% Tween 20 as a surfactant. Devilbiss〓152
(Devilbiss〓152) Spray corn plants at a rate of 10 mg per plant or 20 mg per plant during the early stages of reproductive differentiation using a sprayer. Results are analyzed by comparing treated plants to control plants that are not chemically treated.
A chemical is considered active in altering the reproductive development of a corn plant if the treatment results in at least a 25% inhibition of lateral drapery formation compared to control plants. Through the above procedure, it was found that compounds 1, 4 and 5 were effective in inhibiting the growth of lateral pedicels by 50 to 74%. Compounds 2, 6 and 7 were found to be effective in inhibiting lateral flower development by 25-49%. Furthermore, as shown in the table, flowering is suppressed. Table Compound Length (mm) Control 224 1 67 2 132 3 75 Furthermore, the methyl ester of N-(2-chloro-3-pyridyl)phthalamic acid obtained in Example 8 was added according to Test Example A above. It was treated as a plant growth regulator. The drug was sprayed on corn at a rate of 15 mg after two weeks of growth. The number of corn fields was approximately 25,000 per hectare. Data were collected after 8 weeks. The above-mentioned phthalate esters have no chemical toxicity, and the amount of corn treated is only 75%.
It showed only ~99% infertility. Test Example B In another test, N-(2-chloro-3
-pyridyl) phthalamic acid is applied to corn plants as the formulation described above. Significant responses include changes in panicle height, increased panicle silking rate, and partial sterility. The table shows significant reactions.

Table 1 As exemplified above, the present invention contemplates the application of the phthalamic acids described above before or during the early stages of reproductive differentiation. Reproductive differentiation occurs at different times depending on the type of corn plant and environmental factors. For example, androgenetic differentiation of gasbean corn begins during kernel formation, whereas reproductive differentiation of maize A-619 occurs within the first 8 to 12 hours after germination.
Starts within days. Determination of when reproductive differentiation occurs is subject to those skilled in the art. By way of example and for purposes of illustration only, applications for most varieties used in the Midwest United States are preferably applied between 3 and 25 days after germination. For varieties used abroad, it may be necessary to apply between 1 and 40 days after germination. The following example shows the case of corn variety A-619 at 7 to 12 days after germination.
Indicates that it is preferable to apply during the day. Test Example C Corn variety A-619 is sown at a rate of 64,000 plants per hectare. Compound 5,
These were applied at a rate of 0.56Kg to 1.68Kg per hectare using a formulation consisting of 50% acetone, 0.25% Tween 20 and sufficient water for the formulation to be applied at a rate of 320Kg per hectare. Process the plants. In some cases the application is carried out early, ie on or before the 12th day after germination. In other cases, the application is carried out late, ie after 12 days after germination. Post-harvest, the yield of treated plants is compared to that of untreated control plants. The table shows the results of this test.

In the practice of this invention, the active ingredients can be used alone or in combination with liquid or solid substances, referred to in the art as adjuvants. To produce plant growth regulating compositions, the active ingredient is mixed with adjuvants, including diluents, fillers, carriers and regulators, to form finely divided finely divided solids, granules, pills, moisturizers, etc. Compositions in the form of powders, dusts, solutions and aqueous dispersions and emulsions are provided. The active ingredient can therefore include auxiliaries such as finely divided solids, liquids of organic origin as solvents, water, wetting agents,
It can be used with dispersants or emulsifiers or any suitable combinations thereof. Specific examples of finely divided solid carriers and fillers useful in the plant growth regulating compositions of the present invention include talc, clay, pumice, silica, diatomaceous earth,
Quartz, acid clay, sulfur, powdered cork, wood powder,
Examples include walnut powder, white seal, tobacco powder, charcoal powder and their similar substances. Typical liquid diluents include Stoddard's solvent, acetone, alcohols, glycols, ethyl acetate, benzene and the like. The plant growth regulating compositions of the present invention, particularly liquids and wettable powders, typically contain one or more surfactants in an amount sufficient to render the given composition readily dispersible in water or oil. The term "surfactant" is understood to include wetting agents, dispersing agents, suspending agents and emulsifying agents. Such surfactants are well known and for detailed examples thereof see US Pat. No. 2,547,724. Generally, the active ingredient is applied in the form of a composition containing one or more adjuvants to aid in uniform distribution of the active ingredient when it is applied.
The application of the liquid and particulate solid powder compositions containing the active ingredients can be carried out according to customary techniques, for example using propagators, powder spreaders, automatic and manual atomizers and spray spreaders.
The composition can also be applied from an airplane as a duct or spray. The compositions of the present invention generally contain about 1 to 99 parts of active moiety, about 1 to 50 parts of surfactant, and about 4 to 94 parts of solvent, where all parts of the composition It is based on the weight based on the total weight. When choosing the appropriate application ratio of active ingredients,
It will be appreciated that the exact ratio will also depend on the type of application, plant variety, soil conditions and various other factors known to those skilled in the art. Rates of about 0.056 Kg to 5.6 Kg per hectare are preferred, but higher rates up to 56 Kg per hectare can be used depending on the factors set out above. However, the present invention is not expected to be used in phytotoxic proportions that would exhibit herbicidal effects. It will further be appreciated that one or multiple applications can be used to produce the desired effect. Although the invention has been described with respect to particular embodiments, it is not intended to be limited in detail. It is to be understood that various modifications may be made without departing from the spirit and scope of the invention and such modifications are intended to be included therein.

Claims (1)

[Claims] 1 formula [wherein, R is hydrogen or lower alkyl, and R ₁ is of the formula [formula] [formula] or [formula] (wherein, X is selected from the group consisting of hydrogen, halogen, lower alkyl, and lower alkoxy) Re,
Y is selected from the group consisting of halogen, lower alkyl and lower alkoxy, provided that if the nitrogen atom is present at the 3rd position with respect to the bond in the above formula, then X or Y is the chlorine at the 4th position with the same meaning. and if the nitrogen atom is present in the 3-position with respect to the bond in the above formula and X is hydrogen, then Y cannot be a lower alkoxy group in the 4-position in the same sense). a substituted pyridyl] and agriculturally acceptable salts thereof. 2 As the active ingredient, the formula [wherein, R is hydrogen or lower alkyl, and R ₁ is of the formula [formula] [formula] or [formula] (wherein, X is selected from the group consisting of hydrogen, halogen, lower alkyl, and lower alkoxy) Re,
Y is selected from the group consisting of halogen, lower alkyl and lower alkoxy, provided that if the nitrogen atom is present at the 3rd position with respect to the bond in the above formula, then X or Y is the chlorine at the 4th position with the same meaning. and if the nitrogen atom is present in the 3-position with respect to the bond in the above formula and X is hydrogen, then Y cannot be a lower alkoxy group in the 4-position in the same sense). A reproductive and growth regulator for corn plants, which comprises a compound having the following formula or an agriculturally acceptable salt thereof: substituted pyridyl.