KR820000009B1 - Process for preparing imidazolinyl benzoate - Google Patents

Abstract

Title compds. (I; X = -OR3(R3 = H, C1-12 alkyl, substituted C3-5 alkynyl, C3-5 alkenyl), -NR4R5(R4,R5 = H, C1-4alkyl, C3-5 alkenyl, C3-5 alkinyl, benzyl; R1 = C1-4 alkyl; R2 =C1-6 alkyl, C3-6 cycloalkyl, C2-4 alkenyl) and their acid addition salts useful as plant growth regulators, were prepd. by reaction of II and alkali metal akoxide, amine or HCl. Thus, sodium propagyl alcoholate(III) was prepd. by reaction of 12.5 ml propagyl alcohol and 0.1 g NaOH under N2 blanket. 5.0 g II(R1 = CH3; R2 = CH(CH3)2) was mixed with III and HCl was added to give 6.02 g I (R1 = CH2; R2 = CH(CH3)2) X = OCH2CH2-CH3).

Description

Method for producing imidazolinyl benzoates

The present invention relates to a method for preparing imidazolinyl benzoates of the following structural formula (I) useful as plant growth regulators.

(여기서 R₄와R₅는 각기 수소, 알킬 C_1∼C_4,알케닐 C_3∼C₅, 알키닐 C_3∼C₅또는 벤질임) 및 R₁과 R₂가 상이한 치환분인 경우 그의 광학이성체이며; R₁은 알킬 C_1∼C₄이고, R₂는 알킬C_1∼C_6,사이클로알킬C_3∼C_6,알케닐C_2∼C₄이며; X가

인 경우 R₂는 또한 페닐, 할로페닐 또는 벤질이며, R₁과 R₂는 그들이 부착되어 있는 탄소와 함께 메틸로 임의 치환된 사이클로알킬 C_3∼C₆을 형성할 수 있다.Wherein X is -OR ₃ , wherein R ₃ is hydrogen, alkyl C ₁ -C ₁₂ , an alkynyl C ₃ -substituted with one halogen-substituted moiety, preferably chlorine or substituted with 1-2 methyl-substituted moieties C _5, a halogen substituted min, preferably alkenyl of Al substituted by chlorine or methyl-substituted, or 1 to 2 minutes, C ₃ ~C _5, benzyl, cyclohexenyl-methyl, pentadienyl, or an alkali metal, ammonium and Is a salt-forming cation selected from the group consisting of aliphatic ammonium) and acid addition salts thereof (except salt-forming cations) or X is

Wherein R ₄ and R ₅ are each hydrogen, alkyl C _{1 to} C _4, alkenyl C _{3 to} C ₅ , alkynyl C _{3 to} C ₅ or benzyl, and when R ₁ and R ₂ are different substituents, Optical isomers; R ₁ is alkyl C _{1 to} C ₄ , R ₂ is alkyl C _{1 to} C _6, cycloalkyl C _{3 to} C _{6, alkenylC 2 to} C ₄ ; X

R ₂ is also phenyl, halophenyl or benzyl, and R ₁ and R ₂ together with the carbon to which they are attached may form cycloalkyl C _{3 to} C ₆ optionally substituted with methyl.

Aliphatic ammonium means monoalkylammonium, dialkylammonium, trialkylammonium, monoalkenylammonium, dialkylammonium, trialkenylammonium, monoalkynylammonium, dialkylammonium, trialkynylammonium, monoalkanolammonium, It refers to an ammonium group of dialkanolammonium and trialkanolammonium, and the aliphatic ammonium group contains a total of 1 to 18 carbon atoms.

Preferred compounds for use as plant growth regulators, particularly as dwarf agents for crops, leafy plants for eggplant plants and herbaceous plant biocides, are X ₃ OR ₃ , R ₁ is alkyl C ₁ -C ₃ ; When R ₂ is alkyl C _{1 to} C ₃ and R ₁ and R ₂ represent cyclohexyl together with the carbon to which they are attached, R 3 is alkyl C _{1 to} C ₁₂ , _{1 to} 2 methyl substituted or one chlorine substituted. Alkenyl C _{3 to} C ₅ optionally substituted with powder, alkynyl C _{3 to} C ₅ optionally substituted with methyl substituted powder; And benzyl, cyclohexenylmethyl or pentadienyl. The compound of formula (I) and acid addition salts thereof. More preferred compounds of formula (I) are those wherein X is OR ₃ , R ₁ is methyl, R ₂ isopropyl and R ₃ is as described above.

The imidazolinyl benzoate of the general formula (I) according to the present invention, wherein R ₃ is a substitution other than hydrogen, an alkali metal, ammonium or an aliphatic ammonium, may be a suitable alkali of imidazoisoindoledione of the general formula (II). It may be prepared by reacting with a metal alkoxide. The reaction is preferably carried out at a temperature of 20 ° C. to 50 ° C., under an inert gas blanket.

Generally, the alkali metal or alkali metal hydride is mixed with a suitable alcohol and then the mixture is mixed with imidazole isoindoledione (II).

Inert gases that can be used in the blanket in this reaction are preferably nitrogen, argon, helium or nitrogen.

Alkali metal and alkali metal hydrides that may be used include sodium, sodium hydride, potassium, potassium hydride, lithium, lithium hydride.

Schematic of this reaction is as follows.

Wherein R ₁ , R ₂ , and R ₃ are as described above.

In this reaction, the alcohol acts as a reactant and a solvent. In this case, no secondary solvent is required, but if expensive alcohol is used for the reaction and / or excess alcohol is required to create optimum reaction conditions, the reaction mixture may be inexpensive secondary such as dioxane, tetrahydrofuran or other aprotic solvents. Preference is given to adding a solvent.

The amount of aprotic solvent added to the reaction mixture varies but generally does not exceed four times the alcohol used.

The ratio of secondary solvents that may be used in the process of the present invention to alcohols is therefore about 0.0: 1 to 4.0: 1.

The imidazolinyl benzoate of the general formula (I) may be a tautomer. For convenience, they are represented by one structural formula such as general formula (I), but they may exist in an isomeric form as follows.

Wherein R ₁ , R ₂ and R ₃ are as described above.

Thus, one general formula (I) contains both the two isoform imidazolinyl benzoates.

These are amphoteric compounds, soluble in both acidic and alkaline aqueous solutions. They form acid addition salts of imidazolinyl benzoate (I) when treated with strong acids, especially strong inorganic acids such as hydrochloric acid, sulfuric acid or hydrobromic acid.

When R ₁ and R ₂ are the aforementioned groups on imidazolinyl benzoate of general formula (I), the carbon atom to which they are attached becomes a subsidiary carbon atom.

Thus the products (as well as their intermediates) are present as d-, 1- and d1-forms.

Thus the d- or l-form is reacted with a suitable optically active d- or l-imidazoisoindoledione (II) with a suitable alcohol (III) to give the corresponding d- or 1-imidazolinyl benzoate ( Easily produced by producing I).

X is OR ₃ , R ₃ is hydrogen, and R ₁ and R ₂ are compounds of the general formula (I) as described above in which the imidazo isoindoledione of general formula (II) is mixed with water such as tetrahydrofuran or dioxane. It can be prepared by reaction with excess hydrochloric acid in the presence of a chemical solvent.

This reaction produces lactone hydrochloride of formula IV, which is treated with one equivalent of a base such as sodium hydroxide, potassium hydroxide or sodium carbonate to produce the corresponding acid.

This reaction is produced as follows.

The resulting imidazolinylic acid can be converted to the corresponding alkali metal, ammonium or aliphatic ammonium.

If an alkali metal salt is desired, the acid is treated with an alkali metal hydroxide concentrated solution and then water is removed via azeotropic distillation, preferably with an organic solvent such as dioxane.

Ammonium or aliphatic ammonium salts can be prepared in a similar manner except by partially dissolving the formula (I) acid in lower alcohols such as methanol, ethanol, isopropanol and treating the resulting solution with ammonia or a suitable aliphatic amine. The reaction mixture is then concentrated and the residual solid is treated with hexane and dried to recover the ammonium or aliphatic ammonium salt of formula (I).

Aliphatic ammonium salts of the compounds of the present invention are prepared from organic amines having a molecular weight of about 300 or less.

These amines include methylamine, ethylamine, n-propylamine, isopropylamine, n-butylamine, isobutylamine, sec-butylamine, n-amylamine, iso-amylamine, hexylamine, heptylamine, octylamine , Nonylamine, decylamine, undecylamine, dodecylamine, tridecylamine, tetradecylamine, pentadecylamine, hexadecylamine, heptadecylamine, octamesylamine, methylethylamine, menylisopropylamine, methylhexyl Amine, methylnonylamine, methylpentadecylamine, methyloctadecylamine, ethylbutylamine, ethylheptylamine, ethyloctylamine, hexylheptylamine, hexyloctylamine, dimethylamine, diethylamine, di-n-propylamine , Diisopropylamine, di-n-amylamine, diisoamylamine, dihexylamine, di-heptylamine, dioctylamine, trimethylamine, triethylamine, tri-n-propylamine, triisopropylamine, Tri-n-butylamine, triisobutylamine, tri-sec-butylamine, n-amylamine, ethanolamine, N-propanolamine, isopropanolamine, diethanolamine, N, N-diethylethanolamine, N-ethylpropanolamine, N-butylethanolamine, allylamine, n-butenyl- 2-amine, n-tentenyl-2-amine, 2,3-dimethylbutenyl-2-amine, di-butenyl-2-amine, n-hexenyl-2-amine and propylenediamine.

The imidazolinyl benzamide of the following structural formula according to the present invention can be prepared by reacting the imidazoinoindoledione of the general formula (II) with an amine of the general formula (III).

Wherein R ₁ , R ₂ , R ₃ and R ₄ are as described above.

The molar ratio of amine (III) to imidazoisoindoledione (II) should be in the range of from 1: 1 to 10: 1 and preferably from 2: 1 to 5: 1.

The reaction is preferably carried out in non-protic solvents such as tetrahydrofuran, dioxane, toluene, xylene, benzene at a temperature of 50 ° to 100 ° C.

Schematic of the reaction is as follows.

Wherein R ₁ , R ₂ , R ₃ and R ₄ are as described above.

When R ₁ and R ₂ are different substituents, the carbon to which R ₁ and R ₂ are attached is a subsidiary carbon element and the product (and intermediate thereof) is present in d-, 1- and d1-forms. In addition, when imidazoisoindoledione (II) is optically active, the d- or 1-form reacts with the structural formula (III) amine, R ₄ R ₃ NH, and the corresponding d- or 1-amidazolinylbenzamide ( I) is formed.

The compounds of the present invention are very effective as plant growth regulators. They can be effectively used to control relative stem and / or leaf juice growth of monocotyledonous and dicotyledonous plants by applying them to the leaves, stems, roots, or seeds of the plant or to the soil in which the plant grows. Generally valid for one application to plants, but can be repeated as needed.

The most characteristic growth changes resulting from the treatment of the compounds of the present invention with plants are the thickening and shortening of the stems and the reduction of leaf juice growth. As such, the structural formula (I) compounds of the present invention are useful for preventing dwarfing (ie, decreasing relative stem growth) and occupation of pollen and crops such as barley, oat, wheat, rice, and corn. Surprisingly, the compounds of the present invention are also effective in reducing the relative stem growth of soybeans and crops, in particular soybeans such as Gangnam beans, soybeans, green beans, lima beans.

In general, in order to obtain this dwarf effect, it is preferable to use about 0.0002 to 4.48 kg / ha, preferably 0.11 to 2.24 kg / ha, of the compound of general formula (I).

The plant growth control effect of the compounds of the present invention is also shown to regulate the growth of the leaf juice in herbaceous and woody plants such as tobacco and coffee to achieve more desirable plant growth.

In order to control the growth of the liquor of the coffee tree, the trunk of the tree is usually treated by spraying or applying with active imidazolinyl benzoate I.

In fact, this amount is about 0.5 to 2.60 kg of active ingredient per hectare.

A solution containing from 1 to 150 mg, preferably 1 to 40 mg, preferably 1 to 40 mg per heter in the leaves of the plant and 85 to 120 mg in the soil in which the plant grows to prevent blotting growth on mechanically trimmed tobacco plants; and / Or it has been found effective to use suspensions, preferably aqueous solutions and / or aqueous suspensions.

In practice, about 0.5 to 2.0 kg of active ingredient per hectare are used.

In tobacco cultivation, harvesting of crop crops begins by eliminating normalized growth of tobacco plants through so-called topping.

This process usually facilitates the growth of large leaves that make up the harvest.

However, this growth is subtracted by strengthening the growth of the livestock (leaf juice) buds.

Livestock growth (so-called blotting) reduces the nutrient supply to be used to control broadleaf growth. Therefore, it is essential to control the growth of tobacco plants when optimal production of marketable leaves is achieved.

Control of aerobic growth is achieved by using active ingredients as much as the amount of germination growth on tops of tobacco leaves or soil where they grow.

The imidazolinyl benzoate (I) of the present invention is poorly soluble in water and therefore they are generally formulated as fluids dispersed in water or other inexpensive liquid diluents for use as wet powders, emulsifiable concentrates or liquid sprays. .

The compounds of the present invention may generally be prepared in granules containing about 5% to 15% of poisons.

Generally, the wet powder is about 25-80% by weight of imidazolinyl benzoate, about 2-5% by weight of surfactants (e.g. sodium N-methyl-N-oleoyltaurate, alkylphenoxypolyoxyethylene ethanol Or 5-10% by weight dispersant (e.g., fixed lignosulfonate), 25-63% by weight of finely ground carriers (e.g. kaolin, diatomaceous earth, attapulgite) It is prepared by mixing and grinding.

The most typical composition prepared according to the above formulation is 50% by weight of 1-methyl-2-propynyl 0- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) benzoic acid ester 3% by weight of sodium N-methyl-N-oleoyl taurate, 10% by weight of sodium lignosulfonate, and 37% by weight of kaolin.

The flowable liquid composition is 40 to 60% by weight of imidazolinyl benzoate 2 to 3% by weight of concentrated naphthalene sulfonate sodium, 2-3% by weight of gel clay, 2% by weight of propylene It can be prepared by mixing and grinding glycol and 54 to 32% by weight of water together.

Typical granular compositions can be prepared by dissolving or dispersing the active ingredient in a solvent and adding the poison to an adsorbent or nonadsorbent carrier such as attapulgite, corn cobs, pumice, talc.

The invention is illustrated in detail by the following examples.

Example 1

2-propynyl 0- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) benzoate

To 12.5 ml of propargyl alcohol is added 0.1 g of a 50% suspension in mineral oil of sodium hydride. The addition is carried out under a blanket of nitrogen while stirring the mixture and maintaining the temperature at 20 ° C. to 25 ° C. by external cooling.

The sodium salt of propargyl alcohol is completed within 1 to 2 hours. To this solution is added 5.0 g of 3-isopropyl-3-methyl-5H-imidazo [2,1-2] isoindole-2 (3H), 5-dione and the mixture is stirred overnight at room temperature under a blanket of nitrogen.

If incomplete reaction is indicated by thin layer chromatography, further 50 mg of 50% suspension in sodium hydride oil is added to the reaction mixture.

After stirring overnight the mixture was cooled to 5 ° C. and 0.7 ml of 3N hydrochloric acid was added.

The mixture is diluted with methylene chloride and washed with water, then the organic phase is dried and concentrated in vacuo.

The crystalline residue was transferred to a filter funnel using hexane and air dried to produce 2-propynyl Q- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl at a melting point of 131-144 ° C. 6.02 g of benzoate is obtained. Similar reactions are recrystallized from acetone-hexane to give pure product with melting point 145-147 ° C.

Example 2

Structural Formula (I) Preparation of Imidazolinyl Benzoate

Propargyl alcohol is substituted with a suitable alcohol and 3-isopropyl-3-methyl-5H-imidazo [2,1-a] isoindole-2C3H), 5-dione, is substituted with a suitable imidazoisoindoledione. The following imidazolinyl benzoate was prepared in a similar manner to Example 1 except for the following.

Schematic of the reaction is as follows.

Example 3

1,1-dimethylallyl 0- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) benzoate. Hydrochloride

164 mg of 1,1-dimethylallyl 0- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) benzoate (0.5 mmol) was dissolved in 5 ml of methylene chloride and 5 ml of anhydrous ethanol. 0.5 ml of 1.0 N hydrochloric acid is added to the solution. The mixture is concentrated in vacuo and the residue is treated with ether to give crystalline product which is filtered off and washed with ether and air dried to give 170 mg of hydrochloride with melting point 259-262 ° C. (decomposition).

The melting point of these and other salts depends on the heating rate.

Example 4

Preparation of 0- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) -N, N-dimethylbenzamide

68 g of dimethylamine in a cold solution obtained by dissolving 180 g of 3-isopropyl-3-methyl-5H-imidazo [2,1-a] isoindole-2- (3H) and 5-dione in 300 ml of anhydrous tetrahydrofuran in a pressure bottle Add.

The bottle is sealed and heated to 50 ° C. for 16 h with stirring.

Cool the mixture and transfer the contents of the bottle to the flask.

The solvent is removed in vacuo. The crystalline residue was suspended in ether, filtered, washed with ether and air dried to yield 0- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-with a melting point of 144-146 ° C. 195 g of N, N-dimethylbenzamide is obtained. This product is recrystallized from acetonitrile to obtain a pure product having a melting point of 147 to 150 ° C.

Example 5

Preparation of Formula I Imidazolinyl Benzamide

A compound of the following structural formula is obtained using a method similar to Example 1 except for replacing dimethylamine with a suitable amine and a suitable imidazo [2,1-a] isoindole-2 (3H), 5-dione.

Example 6

Plant Growth Regulatory Effects of Test Compounds Used on the Leaves of Plants

To assess the effect of the test compound as a plant growth regulator that reduces the relative stem growth of barley, the compound is dissolved or dispersed in a 50/50 water / acetone mixture and applied to the leaves of seedling plants growing in a cup of about 7.5 cm ² . did.

이란 상품명으로 시판되고 있다.A sufficient amount of spreader-sticker was added to the mixture to about 0.1% by weight of the mixture. The main reagents used as spreader-stickers are alkylarylpolyethoxyethanols, free fatty acids and mixed fatty acids, glycol ethers (di-alkyl), benzenedicarboxylates and isopropanol. This spreader-sticker has a specific gravity of 0.90 at 20/20 ° C., a density of 898.5 g / L at 20 ° C., a surface tension of 30 dynes / cm in a 0.1% aqueous solution, and a pH of 6 ± 0.5 as a liquid spray film. This is BIO- from Colloidal Products, Inc. of San Solito, California.

It is marketed under the trade name Iran.

The test compound in acetone: water (1: 1) is sprayed onto seedling barley at a rate of 747 liters per hectare using a nozzle moving at a constant speed along a constant orbit over the plant.

In this test, compounds are used at a rate of 0.11-448 kg per hectare.

The treated plants are placed in a greenhouse bench and watered and fertilized according to the conventional greenhouse growing method.

Three weeks after the plants are treated, some are cultivated and weighed.

The heights of the control and treatment groups were measured and reported in Table 1 below. The various barley used in some of the tests are listed below with their abbreviations.

Barley Type About Ching

Villa v

Mexico M

Larker L

Conquest C

Trial T

Early E

Mona mo

The dwarfness rate of all barleys treated is shown in Table 1 below.

TABLE 1

Relative stem growth deterioration effect determination of barley of imidazolinyl benzoate compound having the following structure.

TABLE 1

Determination of the effect of reducing the relative stem growth of barley (Larker species) of the test compound having the following structural formula.

Example 7

Evaluation of the Effect of Imidazolinyl Benzoate on the Relative Stem Growth of Corn and Gangnam Beans

The effect of lowering the relative stem growth of imidazolinyl benzoate corn and gangnam bean was observed using the same method as in Example 6 except using corn and gangnam bean instead of barley.

The various kidney beans used in the test were Greensleeves and the corn was Field Corn FR 619.

TABLE 2

Determination of the effect of reducing the relative stem growth of corn and kidney beans of imidazolinyl benzoate having the structure

Example 8

Evaluation of the Effect of Imidazolinyl Benzoate to Reduce Relative Stem Growth of Barley and Soybeans

The evaluation method applied in the following test is substantially the same as Example 6 mentioned above. However, the plant species used are Larker barley and Fiskby V soybeans. Moreover, it did not report and record the exact measurement, but evaluated it according to the following index.

% Change in fresh or dry weight or size

50% reduction

2. 35-50% reduction

3. 20-34% ˝

4. 1-19% ˝

5. 0-10%

This test data is reported in Table 3 below.

TABLE 3

Determination of the Effect of Degrading Stem Growth of Barley and Kidney Beans of Imidazolinyl Benzoate Having the Following Structure

Example 9

"Snaptest" wheel test

To measure how hardened the stem and plant stems are by the treatment of the test compound, a handful of plants is pushed sideways at an angle of about 45 ° from just below the seed head.

Repeat this process six times per plot.

Measure the force applied to the stem and the force and speed when they snap back to the vertical position.

The grade is relative because it is based solely on feeling. Use the numbers 1-5 to indicate the weakest stem and 1 to the 5 most rigid stem. This test is carried out with all the cropped edges. The crops used in this test were barley and the type was Villa.

The obtained data is reported in Table IV below.

Table IV

Snap test of barley plants

Example 10

The germination inhibition effect of potted young coffee plants was shown by the following test in which the aqueous acid solution of the emulsified concentrate shown in Example II was sprayed on the stems of the young pollen coffee plants. Eight plants were used in one treatment and each plant was treated with about 25, 50 or 100 mg of test compound.

After 107 days of treatment, the average number and average size of the leaf buds were measured and recorded. The obtained data is reported in Table V below.

TABLE V

Germination of Coffee Plants

Example 11

25% by weight of 2-propynyl 0 (5-isopropyl-5-methyl- (4-oxo-2-imidazoline) to determine the effect of the compounds of the present invention on reducing the number of shoots growing on coffee trees -2-yl) benzoic acid, methyl ester, dispersed in 50% by weight of cyclohexanone, 15% by weight of heavy aromatic solvent (Hi Sol) and 10% by weight of nonionic emulsifier (T Mulz 339) Two pounds of aqueous acid solution was prepared.

The emulsion concentrate was dispersed in a sufficient amount of water to prepare a dispersion containing 2000 mg of active compound per 90 ml of water.

The stems of 15-year-old Mundo Novo coffee plants are cut off at 0.6 m from the soil and treated with one 90 ml of test solution per branch, one of two branches per hill. This corresponds to 2.860 kg / ha of active ingredient.

After 60 days of stem treatment of the coffee tree, the average number and size (cm) of the shoots were measured and examined.

In the untreated stems in this test, the stems treated with an average of 15.3 3.7 cm salts had an average shoot of 4.3 cm per stem.

Example 12

The following tests were conducted to determine the effect of the tobacco plants of the compounds of the present invention as the leaf juice growth inhibitors.

In this test, 10 mg of test compound was dispersed or dissolved in 200 ml of 50/50 acetone / water.

The 8-week-old tobacco tree was mechanically sharpened and sprayed with 40 ml of test solution containing 2 mg of active ingredient.

The treated plants were placed in greenhouse vents and grown according to the greenhouse cultivation method. After 3 weeks of treatment all plants (5 per treatment) were examined to determine the number of bloat per plant and the data obtained are shown in Table VI below.

[Table VI] Leaf juice growth inhibition in tobacco

Example 13

The following test was conducted to determine the effect of the compound of the present onset as a leaf juice growth inhibitor in tobacco plants.

In this test, the tips of 6-week-old Xantia tobacco plants were trimmed and sprayed with 30 ml of acetone / water 50/50 containing 1-5 mg of test compound.

Three weeks after spraying, the number of suctions on the tree was counted, removed and weighed. Five trees were used for one treatment and the results were averaged. The results obtained are reported in Table VII below.

[Table-Ⅶ] Tobacco Germination Jersey

Example 14

Determination of the Effect of Imidazolinyl Benzamide to Reduce Stem Growth in Corn and Kidney Beans

Corn and kidney beans were used instead of barley and tested according to the method of Example 6.

In this test, corn and kidney bean seedlings were sprayed with a water / acetone (1: 1) mixture containing a sufficient amount of test compound. 0.056 to 6.72 kg / hectare of test compound was used in one treatment.

The corn and kidney beans used in this test were Field Corn FR-619 and Green Sleeves, respectively.

Stem growth reduction of treated plants is evident from the data obtained in this test and the results are reported in Table VII below.

[Table VII]

Determination of Relative Stem Growth Degradation Effects of Corn and Kidney Beans of Test Compounds with the Following Structure

Example 15

In this test, 21-day-old soybean seedlings were sprayed with a solution or dispersion in which the test compound was dissolved or dispersed in a 50/50 water / acetone mixture. The test solution or dispersion contains a sufficient amount of the test compound and when sprayed on the plant as in Example (I), the plant leaves are sprayed in an amount of 0.033 or 0.11 kg / hectare.

The test solution contained 0.1% by weight of the same spreader-sticker as in Example 3 above.

After spraying, the plants are placed in greenhouse benches and watered and fertilized according to the greenhouse cultivation method.

After two months of treatment, the plants are planted in 18 cm pots and placed back into the greenhouse for further growth.

The test is completed 12 weeks after spraying. The plants are inspected, harvested, weighed, weighed and weighed, and the pods are dried and weighed again.

Two soybeans were used in this test, Bragg and Fiskeby V. Using five plants per treatment, the results were measured as height, pod generation and average weight of pods. The data obtained are shown in Table VII below.

Table 1-Determination of the Effect of Imidazolinyl Benzoamide on the Relative Stem Growth and Yield of Soybean

Example 16

Determination of the Effect of Imidazolinyl Benzamide on Tobacco Suction Regulator

To measure the inhibitory effect of the test compound on germination growth of tobacco plants, the tip of xanthia tobacco plants growing in 18 cm pots was polished. Three days after trimming, when the shoots grew to a length of 1-1.5 cm, water / acetone (1: 1) solution or dispersion of the test compound was sprayed. A solution or dispersion containing 0.1% by weight of spreader-stucker as in Example 6 and 20 or 100 mg of test compound per liter was used.

Each plant was sprayed with 200 ml of solution containing 4 or 20 mg of test compound. Five plants were used in one treatment. After spraying, the plants were placed in greenhouse benches and grown according to the greenhouse cultivation method. Three weeks after treatment all plants were examined and recorded. Untreated plants and plants treated with maleic hydrazide (traditional deodorant) were used as controls.

The data obtained are shown in Table VII below.

Here, 20 mg of the test compound showed a germination inhibition rate of 78.9%, whereas a general germination inhibitor showed an inhibition rate of 64.0% of wool.

[Table Ⅹ] tobacco bud jersey

Claims (1)

A process for preparing the compound of formula (I) characterized by reacting an imidazo isoindoledione compound of formula (II) with an alkali metal alkoxide, amine or hydrochloric acid and a base

Wherein X is OR ₃ (where R ₃ is hydrogen, alkyl C ₁ -C ₁₂ , one halogen substituent, preferably chlorine or alkenyl C ₃ -C ₅ , substituted with 1-2 methyl substituents, one A halogen substitution of, preferably consisting of alkynyl C ₃ -C ₅ , benzyl, cyclohexenyl methyl, pentadienyl, or an alkali metal, ammonium and aliphatic ammonium, substituted by chlorine or 1-2 methyl substitutions Is a salt forming cation selected from the group) and R ₃ is an acid addition salt thereof if it is not a salt forming cation, or one X is

(Wherein R ₄ and R ₅ are each hydrogen, alkyl C ₁ -C ₄ , alkenyl C ₃ -C ₅ , alkynyl C ₃ -C ₅ or benzyl) and when R ₁ and R ₂ are different substituents, Isoisomer, R ₁ is alkyl C ₁ -C ₄ and R ₂ is alkyl C ₁ -C ₆ , cycloalkyl C ₃ -C ₆ , alkenyl C ₂ -C ₄ ; X

R ₂ is also phenyl, halophenyl or benzyl, and R ₁ and R ₂ together with the carbon to which they are attached can form a cycloalkyl C ₃ -C ₆ optionally substituted with methyl.