前苏联专利SU1743329A3 Method for controlling growth of plants

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专利摘要:
A plant growth regulant containing a benzamide derivative of the formula: <CHEM> wherein R is hydroxyl, alkoxy, alkoxyalkoxy, alkoxyalkoxyalkoxy, alkenylalkoxy, alkenylalkoxyalkoxy, alkynylalkoxy, alkynylalkoxyalkoxy, monoalkylamino, dialkylamino or O-cat wherein cat is an inorganic or organic cation.
公开号:SU1743329A3
申请号:SU884355406
申请日:1988-03-04
公开日:1992-06-23
发明作者:Мотеги Такео；Сакураба Ясуя；Игути Хироюки；Касахара Каору
申请人:Ходогая Кемикал Ко, Лтд (Фирма)；
IPC主号:

专利说明:

The invention relates to chemical agents affecting the growth and development of plants, and may find application in agriculture.
The purpose of the invention is to increase the retardant effect.
Compounds possessing this kind of activity can be used as a means of reducing the lodging of grain crops, for mowing lawns, for chemical pruning, for delaying flowering, suppressing marksman, etc.
As a means for reducing the lodging of rice, the proposed compound is sprayed onto the leaves of plants at a dose of 0.5-5.0 g / ap as an active ingredient in the following period of time: 30 days before heading - earing.
In the case of processing wheat, barley or rye, the compound is applied in the same way at a dose of 1.5-15.0 g / ap.
For mowing a lawn in the case of Cynodon, Paspalum, Eragrotstis or Axonopus treatment, the compound is used in a dose of 1.5-15.0 g / ap when processing leaves in periVI CO
with you

with
one when you need a haircut or a few days after the haircut. If necessary, processing can be repeated.
If the compound is used as an agent to inhibit the growth or reduce pruning of trees, including fruit trees, this compound is used when treating the leaves at a dose of 10-15 g / ap starting before the growth period and ending with the initial growth stage, in spring and autumn, or a week before pruning, or after pruning, when new branches grow a few centimeters.
For stimulating or growth of flower buds, the proposed compound is used in dos. O - -2.0 g / ap to bud formation.
To delay flowering, the compound is applied at a dose of 0.1-5.0 g / ap, during the bud growth period.
As a means for thinning fruits, the compound is applied in a dose of 0.1-2.0 g / ap for 1 month, starting from the full bloom period.
In order to suppress root crops or increase the sugar content in sugar cane, the compound is applied at a dose of 5-20 g / ap prior to the formation of a peduncle, or applied to the place where the color is emitted in the form of a highly concentrated solution.
In order to improve the preservation of root crops, the compound is applied at a dose of 10-30 g / ap in the following period: 3 weeks before harvesting - 1 week before harvesting.
In order to increase the sugar content in cereals, such as sugar cane, the compound is applied at a dose of 10-50 g / ap over a period of time: 1 month before earing - just before earing.
In tab. 1 shows the compounds according to the invention.
The proposed benzamic derivatives can be obtained by reacting 4-hydroxy-M- (2,3-dichlorophenyl) benzamine with various esters of 2-halopropionic acid in an organic solution, such as acetone, 4-methyl-2-pentanone, toluene, dioxane or N, N-dimethylformamide, in the presence of an inorganic base, such as potassium carbonate or sodium carbonate, or in the presence of an organic base, such as pyridine or triethylamine. As a result of this interaction, the corresponding derivatives of the esters can be easily obtained in good yield. This reaction is usually carried out at 20-160 ° C, preferably 50-130 ° C. Usually, 1.0-2.5 mol, preferably 1.0-1.5 mol, of 2-halopropionic acid ester and inorganic or organic base are used with respect to 1
mol of 4-hydroxy-M- (2,3-dichlorophenyl) -benzamine.
In addition, these ester derivatives can be hydrolyzed at room temperature in an organic solvent, such as dioxane, methanol, acetone or N, N-dimethylformamide, or in a mixture of said organic solvent with water in the presence of an inorganic base, such as sodium hydroxide, but
5, the resulting carboxylic acid derivatives can be reacted with an inorganic halide, such as thionyl chloride, or an organic halide, such as phosgene, in
0 an organic solvent, such as toluene or dioxane, for the preparation of chlorine hydride derivatives. The acid chloride derivatives can then be reacted with various alcohols, alkoxy alcohols, alkoxy alkoxy alcohols, alkenyl alcohols, monoalkylamines or dialkylamines in the presence of an inorganic base, such as potassium carbonate or sodium carbonate, or in the presence of an orohydroxy base, such as pyridine, a triangle or a triangle of a triangle of a triangle of a triangle of a triangle or of a triad. , such as acetone, toluene, diox n or NN-diethylformamide, or in aqueous solution in order to obtain the proposed compounds.
Example 1: Preparation of Compound 3. 28 g of 2-hydroxy- (2,3-dichlorophenyl) benzamine, 20.7 g of potassium carbonate and 23.5 g of ethyl 2-bromopropionate are dispersed in 150 ml
0 M, M-dimethylformamide and incubated for 4 h at 120-130 ° C. After completion of the reaction, the reaction solution is poured into 500 ml of a 2% aqueous solution of hydrochloric acid. The resulting precipitate is filtered off. The crude product thus obtained is recrystallized from toluene, resulting in 35.1 g of the desired compound, ethyl 2-4- (2,3-dichlorophenylcarbamoyl) pheno-hydroxy propionate, in a yield of 92.0% mp. 124.5-12b ° C.
PRI mme R-2. Compound 1 preparation. 19.1 g of ethyl 2-4- (2,3-dichl®phenylcarbamoyl) phenoxy propionate are dissolved in 100
5 ml of methanol and 50 ml of 3 N are added. an aqueous solution of sodium hydroxide. The mixture is stirred for 3 hours at room temperature. After completion of the reaction, the reaction solution was poured into 300 ml of water and acidified with concentrated hydrochloric acid. The precipitate formed is filtered off, washed with a large amount of water, then dried and 17.5 g of the desired compound (2,3-dichlorophenylcarbamoyl) phenyloxy propionic acid are obtained. Yield 98.9%, m.p. 199.5-202 ° C.
Example 3: Preparation of Compound 11.
A mixture containing 3.54 g of (2,3-dichlorophenylcarbamoyl) phenoxy propionic acid, 3.57 g of thionyl chloride and 30 ml of dioxane is stirred at 80 ° C for 4 hours. Excess thionyl chloride and dissolved hydrogen chloride, sulfur dioxide and dioxane is removed to obtain (2,3-dichlouophenylcarbamoyl) phenoxy propionyl chloride as a precipitate. Then, 0.9 g of isopropylamine and 1.68 g of sodium bicarbonate are dissolved in 20 ml of acetone. To this solution, while stirring at room temperature, an acetone solution of the above-mentioned propionyl chloride is added dropwise over 5 minutes. After the addition is complete, the mixture is stirred for another 4 hours at room temperature. The reaction solution is poured into 200 ml of a 2% aqueous solution of hydrochloric acid. The precipitate formed is filtered off, washed with dilute alkaline aqueous solution and water, dried, and then recrystallized from toluene. 3.9 g of the desired compound, M-isopropyl-2- 4- (2,3-dichlorophenylcarbamoyl) phenoxy-propionamide, are obtained. Yield 96.2%, m.p. 204-206 ° C.
Example 4: Preparation of Compound 15.
3.54 g of (2,3-dichlorophenylcarbamoyl) phenoxy propionic acid is dispersed in 30 ml of methanol. Then over the course of 5 minutes, 0.65 g of isopropylamine is added dropwise, while stirring the mixture, at room temperature. After the addition, the mixture is stirred for an additional 30 minutes. Thereafter, an excess of isopropylamine and methanol are removed using a rotary evaporator to obtain 4.1 g of the isopropionic salt of (2,3-dichlorophenylcarbamoyl) phenoxy propionic acid. The yield is 99%, so pl. 192-194 ° C (with decomposition).
PRI me R 5. Means for reducing the lodging of rice.
Known plant growth regulator innabenfid - 4-chloro-2- (a-hydroxybenzyl) isonicotinanilide.
Reduced lodging rice.
The rice field, on which a seedling plant was planted in the middle of the plant, was divided into separate cases 3 x 6 m in size. 30 days before the heading, the treatment was carried out manually: 300 g / ml of granule (in the form of granules) for comparison . At the same time, 20 l and 6 days before the heading, a 2 l / ap diluted solution of the proposed compound was sprayed with a manual sprayer.
After 4 weeks, the length of the stem and panicles were measured in 20 plants. After 6 weeks from an area of 3 m2, they harvested rice and measured all grains (kg / ap) and weight 1000 grains. Lodging was controlled in accordance with a specific schedule of terms and evaluated according to the following standards.
Figure of fumbling: 0 - no lodging; 1 - very slight lodging; 2 - slight lodging; 3 - lodging 50% tilt 45 °, 50% full lodging; 4 - significant lodging; 5 - full lodging.
The evaluation results are presented in Table. 2, where the numerical values are given in percentages relative to the values obtained from the raw plots, and the values given in parentheses in the row for the untreated subdivisions are actually measured values.
Reduced wheat fallen.
The wheat field, planted at the end of September, was divided into plots of 3 x 8 m. Then a dilute solution of the proposed compounds was sprayed using a sprayer with a gas compressor with a spraying rate of 2.5 liters / ap. The earing was at the end of May, and the harvest was in the middle of July.
At the end of ma, i. 1 month after the heading, as well as during the harvest, studies were carried out on various indicators. Studies were carried out similarly to the method described in the rice test example.
The results are shown in Table. 3
Example 6: Study of foliar treatment on various plants (major).
Rice, barley, ordinary beans, a real tomato, lettuce and thin amaranth are grown separately in 60 cm2 porous vegetation vessels. The degree of growth is adjusted to the level of the 2-3rd phase of leaf blooming and the diluted solution of each regulator is applied in an amount of 10 l / ar. After 1 month, growth inhibition is assessed.
The results of the regardant activity are given in table. 4, wherein the evaluation is carried out in accordance with the following standards: 0 is the same as no treatment; 1 - inhibition of growth of about 20% compared with no treatment; 2 - growth inhibition of about 40% compared with no treatment; 3 - growth inhibition of about 60% compared with no treatment; 4 - growth inhibition of about 80% compared to the lack of treatment; 5 - there is no progress in growth after treatment; T - tillering and branching increases significantly; B - leaf burning is observed.
Example Chrysanthemum test.
Cuttings of chrysanthemums were planted in early August, and 2 weeks later they were transplanted into pots with a capacity of 200 m2 of 5 plants per pot. After 2 weeks, the tops of the top were made, and then after 2 weeks, the plants were irradiated at night with electric light for 3 hours. Three pots (plants 5 cm in height) were used as one experimental plot. The proposed compound and diminozyl were sprayed so that the leaves of the treated plant were sufficiently wet (5 ml per pot), then after 1 month, and then after 2 months (during flowering) the studies were carried out.
The research results are summarized in table. 5, where the numerical values are average percentages relative to the data for the untreated plots, and the values in brackets are actually measured values.
Example Test for azaleas.
Azalea trees grown in 200 cm pots were cut to 20 cm. After 1 month, when new buds reached a certain size, plants were sprayed at the rate of 10 ml / pot with diluted solutions of the proposed compounds and compounds for comparison. After 2 weeks thereafter, phytotoxicity was evaluated, and the degree of growth inhibition was assessed 1 month after spraying and 3 months later. Sample estimates for the degree of growth inhibition; 0 is the same as for the untreated area; 1 — inhibition of 20%; 2 - inhibition of 40%; 3 - inhibition of 60%; 4 - 80% inhibition; 5, complete inhibition, growth ceased after treatment.
Phytotoxicity: B-1 - weak leaf fall; B-2 - moderate leaf fall; В-3 - solid leaf fall; C-1 - poor etiolation or yellowing; C-2 - moderate etiolation or yellowing; C-3 - significant etiolation or yellowing.
Other reactions to treatment; S-1 - a weak increase in green color; T-2 - moderate increase in tillering; T-3 - a significant increase in tillering; C-2 moderate enhancement of green color; C-3 - a significant increase in green color; T-1 - weak tillering reinforcement.
The data are given in table. 6
PRI me R 9. Testing spraying on trees x.
Relatively thick shoots from each tree were selected and, when new buds reached 3-5 cm, these shoots were planted into separate areas with a size of 1-2 m. Spraying with a solution was carried out not only from above, but also from the side so that this solution covered all the plants, the dose used was 8–15 l / ap.
After 4 months, shoot growth was evaluated in accordance with the standards given in Example 8.
Data sprayed areas are given in table. 7
The evaluation results are presented in Table. eight.
PRI me R 10. Spraying bermuda grass.
The lawn with T-419 bermuda grass was divided into 3 separate cases of 4 m each. In May, before mowing, the grass was sprayed with a hand sprayer with diluted solutions of the proposed compounds and mefluidid at a dose of 2 l / ar.
After 3 weeks, a study was conducted and the grass was mowed (10 mm height of cut grass), while the weight of the cut grass was measured.
Subsequently, the grass was not mowed and 5 weeks later a comparative assessment was made with respect to the data for the untreated plot.
The evaluation results are presented in Table. 9, where the numerical values are percentages relative to the data for the raw plots, and the values in brackets are actually measured values.
The evaluation was carried out in a manner similar to that described in Example 8, and the density was evaluated according to the following standard: D-0 - normal; D-1 - loose; D-2 - dense; D-3 - high density.
Example 11: Inhibition of development of radish pedicels.
The field of ripening radish, sown in spring and grown just before the development of the pedicel, is divided into divisions so that each division contains 6 plants. The wettable powder, the emulsifiable concentrate, the aqueous solution and the liquid composition are applied in an amount corresponding to 15 liters / ap, using
hydraulic sprayer and hand apply the dust and the composition of microgranules.
After 1 month, the evaluation was carried out as in Example 6.
The results are shown in the table. 10 (the numerical value is the average for 6 plants).
PRI me R 12. The study of foliar treatment on sugar cane.
The field of sugar cane, sown in spring and grown to the initial stage of ripening, is divided into sections so that each contains a plant and 20 ml of a solution having a predetermined concentration of the active component and containing a surfactant are applied by hand. sprayer on the main part of the upper leaves of each stem.
After 2 months, i.e. during harvesting, some earing is observed on the untreated plot, whereas there is no earing in any of the treated areas. Plants are harvested and squeezed. The sugar content of the pressed juice is measured using a polarimeter of sugar content.
The results are shown in the table. eleven.
Example13. The study of foliar processing on the onions.
A field of onions transplanted in the fall and grown to 10 ma, 10 days before harvesting, is divided into sections of 5.4 m2 and a solution having a predetermined concentration of the active component and containing a surfactant is applied on the foliage in an amount of 10 l / are. The height of the plants during application is about 50 cm, and a slight lodging is observed.
After harvesting, 50 onion plants are placed in one layer, not cutting off their leaves, and stored in storage. 30 oct br and 15
but br examine the germination rate and the speed of rotting.
The results are shown in Table. 12.
PRI me R 14. Prolonging the life of cut flowers.
As an experimental unit used 5 cut flowers of carnations and roses. The extension of the life of the cut flowers was estimated according to the following two methods (the test was conducted on the condition of the presence of buds):
a water absorption method in which the active ingredient is added to 200 ml of water in a vase to obtain a given concentration;
an immersion method in which the bud of a cut flower was immersed in a liquid containing the active ingredient in a given concentration for a few seconds, and after the liquid was drained, cut flowers were placed in a vase. The number of days from the beginning of bloom to the state of the last flowers was counted.
The results are shown in tabl. 13.

权利要求:
Claims (1)
[1]
Invention Formula
A method of controlling plant growth involving the treatment with a biologically active substance, characterized in that, in order to increase the retardant effect, a compound of the general formula g is used as the biologically active substance (P
, b HCO-pVoCli-COR,
CH3
where R is hydroxyl, methoxy, ethoxy, butoxy, 2-butoxyethoxy, allyloxy, propargyloxy, diethylamino or o-cation of sodium, calcium, triethylammonium, isopropylammonium, at a dose of 1-30 g / ap.
Table 1
Inabenfid 6fc (granules) Buoyancy in salt water having a relative density of 1.06.
Table3
ten
eleven
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14
15
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comparative)
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0.03
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0.03
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0.3
o.oz
0.1
о.з о.оз
0.1 0.3
0.03
0.1
0.3
o.oz
0.1
о.з
0.03
0.1
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0.03 0.1
о.з
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0.1
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o.oz
0.1 0.3
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0.1
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0.03
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o.oz
0.1 0.3
2
3 T 4.5
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3 T 4.5
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it
4.5
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four
4.5
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about
Table 1
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3
4.5 5
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one
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3
4.5 5
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4 5 5 О О 1
Table5
50
Table 8
nineteen
Dust 2
The composition of the microgranules 2
Emulsifiable concentrate 20
ten
Wettable powder 40
12
Aqueous solution 100
H
Liquid composition 20
1743329
20
E table
Table 10
3.2 A, 2 M
2.6 3.8, 5
3.9 M 5.0
3.1 3.7
,five
3.3
, 2
, 7
3.5, 5 M
Table 12
Table 13

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同族专利:

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EP0281120A3|1990-09-19|

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US4902815A|1990-02-20|

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KR930007421B1|1993-08-10|

DD280685A5|1990-07-18|

CS141688A2|1989-04-14|

US4976768A|1990-12-11|

BR8800979A|1988-10-11|

KR880010669A|1988-10-24|

RO105757B1|1992-12-30|

HU203023B|1991-05-28|

AU1272188A|1988-09-08|

CA1309265C|1992-10-27|

EP0281120B1|1992-09-23|

DK117988A|1988-09-06|

TR23980A|1991-01-14|

CS268195B2|1990-03-14|

EP0281120A2|1988-09-07|

AR243727A1|1993-09-30|

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CN88101138A|1988-09-14|

DK117988D0|1988-03-04|

ZA881523B|1988-08-24|

DE3874773T2|1993-03-25|

PL271010A1|1988-12-08|

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CN1030817C|1996-01-31|

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引用文献:

公开号 | 申请日 | 公开日 | 申请人 | 专利标题

US3907792A|1969-01-31|1975-09-23|Andre Mieville|Phenoxy-alkyl-carboxylic acid derivatives and the preparation thereof|

JPS6358818B2|1978-12-05|1988-11-17|

JPS6254301B2|1979-11-20|1987-11-13|Hodogaya Chemical Co Ltd|

US6329032B1|1997-11-07|2001-12-11|Icc Industries, Inc.|Thermoplastic composition and containers for promoting plant root branching|

US6114431A|1996-11-08|2000-09-05|Griffin Corp.|Plastic composition|

CN103281905B|2010-12-21|2016-10-19|拜尔作物科学有限合伙公司|The sand paper mutant of bacillus and for promoting plant growing, promoting plant health and control disease and the method for insect|

BR112014005654A2|2011-09-12|2017-03-28|Bayer Cropscience Lp|methods to improve health and promote plant growth and / or fruit ripening|

法律状态:

优先权:

申请号 | 申请日 | 专利标题

JP62048716A|JPH06683B2|1987-03-05|1987-03-05|Plant growth regulator|

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