WO1986005069A1 - Composition and process for the preparation of field plants - Google Patents

Composition and process for the preparation of field plants Download PDF

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Publication number
WO1986005069A1
WO1986005069A1 PCT/HU1986/000013 HU8600013W WO8605069A1 WO 1986005069 A1 WO1986005069 A1 WO 1986005069A1 HU 8600013 W HU8600013 W HU 8600013W WO 8605069 A1 WO8605069 A1 WO 8605069A1
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methyl
weight
parts
hydroxy
acetyl
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PCT/HU1986/000013
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French (fr)
Inventor
Sándor BÁLINT
Judit Benczik
Ferenc Fodor
András Horváth
Béla KARÁCSONYI
Elemér TÖMÖRDI
László ZBISKÓ
Sándor GAÁL
Iván GÁRDI
József KARSAI
Endre SEBESTYÉN
Károly SIKI
Csaba SÖPTEI
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Nitrokémia Ipartelepek
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Publication of WO1986005069A1 publication Critical patent/WO1986005069A1/en
Priority to DK523586A priority Critical patent/DK523586A/en

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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/14Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A01N43/16Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom

Definitions

  • the present invention relates to composition and pro cess for the treatment of field plants in order to intensify the plant growth.
  • a 3728-91-KY trimethyl-7-hydroxy-(2,4)-chromene and optionally microelements and/or mesoalements were used.
  • the present invention is aimed at searching such active ingredients for the treatment of field plants, the use of which makes unnecessary the use of active ingredients which are foreign to the structure of compounds in the plant tissue, such as 2- chloro-ethyl-phosphonic acid, and whereby the loading of the environment and the soil with chemicals can be avoided.
  • the present invention is related to controlling the growth of field plants, mainly cereals, maize soya and sunflower and the process can be characterized by treating the plants at vegetativ stage, in case of cereals when growing into bush or at 2 nodes stage at the beginning of earing, in maize at 5-8 leaves stage, in soya on the 4-6. week after emergence at a rate of 0.025 to 2.0 kg/ha with a 4-methyl-7-hydroxy[2H]benzopyran-2-one (4-methyl- umbelliferon) of the general formula (I)
  • R stands for methyl, ethyl, isopropyl , acetyl, chloro-acetyl, propynyl or Cu-, Ni-, Co-, Na- or H- and optionally at a rate of 58 - 117 g metal ion/ha with micro and meso elements, such as boron, magnesium, copper and zinc in the form of water soluble salts and chelates respectively thereof.
  • micro and meso elements such as boron, magnesium, copper and zinc in the form of water soluble salts and chelates respectively thereof.
  • the present invention also provides compositions suitable for the treatment of field plants containing in an amount of 1-60 percent by weight a compound of the general formula (l) - wherein the definition of R is as given above - and optionally in the form of water soluble salts or soluble chelates boron, magnesium, copper, zinc as well as solid or liquid carriers, optionally surfactants.
  • the compositions of the invention contain 0.01 - 0. 625 parts of copper, 0.0075 - 0.83 parts of zinc, 0.01 - 0.65 parts of magnesium and 0.00175 - 0.28 parts of boron as microelement in the form of water soluble salts or chelates calculated on metal ion and related to 1 part of the compound of the general formula (I),
  • compositions are preferably used in the form of tank mixtures in diluted state and if desired the active ingredients are combined prior to use in the tank mixture.
  • 4-methyl-7-hydroxy [2H] benzopyran-2-on can be prepared from aceto acetic acid ester and from resorcinol in the presence of an acidic catalyst by
  • R acetyl melting point: 150-151 oC
  • R propynyl melting point: 138 oC
  • benzopyran derivatives of the general formula (I) is advantageous due to the structure being very similar to the structure of the other aromatic ompounds having phenyl-propane sceleton such as coumarin, esculetin, scopoletin and lignine which can be found in bound form in the tissues of the plants.
  • the active ingredients according to the invention can be considered being analogous with those compounds which are synthetized in the plants and thereby neither the soil, nor the plants are loaded with chemicals which cannot be found in the nature.
  • the compounds of the general formula (I) can be used at a relatively low rate, such as 50 - 500 g/ha.
  • the compounds of the general formula are not toxic to humans or warm blooded animals and can be thus used as pharmaceuticals in human therapy.
  • the active ingredients according to the invention have a further advantage that they do not influence the endogen hormone synthesis in the plants and their effect is presumably due to the fact that they promote the release of indolyl acetic acid synthetized by the plants but being in bound form.
  • Compounds according to the invention are applied in the form of dusting agents, wettable powders or emulsifiable concentrates, which can contain solid or liquid carriers and/or surfactants.
  • surfactants can be non-ionic and anionic, as anionic surfactants salts of aliphatic sulfonic acid esters, salts of aromatic sulfonated compounds, alkali salts of lignosulfonate and as non-ionic surfactants fatty alcohol derivatives of ethylene oxide or propylene oxide, alkyl phenols, oils or fats can be employed.
  • the compositions in concentrated form are diluted prior to use to 0.01 - 4-5 % by weight sprayable compositions.
  • the usual dosis of the compositions is 0.025 - 2.0 kg per hectare, but higher dosis may be used as well for special purposes.
  • compositions according to the invention are suitable for the treatment of monocotyledonous and dicotyledonous field plants, such as cereals, maize, sunflower, cole-seed, sugar beet and soya.
  • Micro- and mesoelements are usually used in the form chelates.
  • chelate forming agent K-p- phenol-lignosulfonate can be used.
  • chelates magnesium chelate at a concentrat ion of 40 g/l copper chelate at a concentration of 40 g/l
  • zinc chelate at a concentration of 30 g/l can be mentioned.
  • the preparation of the chelates as well as the details of the preparation of the compositions according to the invention can be found in the following examples.
  • Example 1 % by weight
  • Example 2 25 g of 4-methyl-umb elliferon are admixed with the sodium salt of 3 g diisobutyl-naphtalene-sulphonic acid, 5 g of the sodium salt of lignine sulphonic acid and with 67 g of kaolin. The mixture is ground and wettable powder is obtained.
  • Micro- and mesoelement compositions are prepared as follows:
  • compositions are prepared from water soluble salts and chelate forming agents so that one liter of the solution contains the given amount of ions.
  • chelate forming agent trimethyl-diamine- 2,2'-hydroxy-5,5'-potassium-potasslum-para-phenol- sulfonate is used.
  • Example 8 % by weight
  • the tests were performed on field cernozjom soil on 2x10 m 2 plots in 4 repetitions by using winter wheat, maize, soya, and sunflower indicating plants.
  • the spray-liquid was sprayed by using a plot spraying machine of the type Patox 20. Amount of spray liquid: 220 l/ha.
  • Micro- and mesoelements were used as disclosed in Example 7.
  • Time of treatment in 2-6 pairs of leaf stage of the plants Compositions and dosis: 4-methyl-7-hydroxy[2H]benzo- pyran-2-one 62.5 g/ha
  • compositions and dosis 4-methyl-7-hydroxy[2H] benzo- pyran-2-one 250 g/ha 500 g/ha 1000 g/ha microelements: 1.0-1.0 l/ha from the composition according to Example 7. Concentration of spray liquid: 0.11-0.68 % by weight /volume related to the active ingredient. Treatment, dosis Crop t/ha % g/ha, l/ha II. III. IV. Average
  • Concentration of spray-liquid 0.011-1.13 % by weight/ volume related to the active ingredient.
  • Example 12 Test-plant: maize Art: Pi-3709 Sowing: April 28. Harvest: November 16. Stook-number: 82.500 stock/ha Weed-killing: N,N-d i-n-propyl-S-ethy l-thiocarbamate

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Composition and process for the treatment of field plants, mainly for regulating the growth of cereals, soya, maize or sunflower at their vegetative or generative stage of development which comprises containing in a total amount of 1-60% by weight 1 part by weight of 4-methyl-7-hydroxy- AD2H BDbenzopyran-2-one or a derivative of general formula (I) - wherein R stands for methyl, ethyl, isopropyl, acetyl, chloro-acetyl, propynyl or Cu-, Ni-, Co-, Na- or H - and optionally in the form of soluble salts or chelates - related to the metal ion - 0.00175 - 0.28 parts by weight of boron, 0.01 - 0.625 parts by weight of magnesium, 0.01 - 0.625 parts by weight of copper and 0.0075 - 0.83 parts by weight of zinc.

Description

COMPOSITION AND PROCESS FOR THE PREPARATION OF FIELD PLANTS
The present invention relates to composition and pro cess for the treatment of field plants in order to intensify the plant growth.
Technical Field
When growing field plants several plant growth regulating agents are used which control the plant growth and plant hormone production, as well as the increase of the inner auxin synthesis. One of the most active agents influencing the hormone balance of the plants is e.g. 2-chloro ethyl phosphonic acid. A special attention, however, has to be paid to the use of the agents influencing the hormone balance of the plants, the growing technology has to be strictly observed as in the opposite case the depression of the plant growth, withering and necrotic symptoms may occur instead of the expected favourable effect.
Background Art
In order to compensate a possible unfavourable effect of 2-chloroethyl phosphonic acid in the vegetative stage of the plant growth a combined method of treatment has been suggested in the published Patent Specification PCT/HU 84/0,0014 where apart from 2- chloroethyl phosphonic acid e.g. 4-chloro-cresol, p-cresol, hydroquinone, p-nitro-phenol, p-chloro- phenol, phenol, resorcinol, pyrogallol, 2,4-dichloro- phenol, 2,6-dichloro-phenol, pyrocatechol, o-butyl- phenol, 4-methyl-7-hydroxy-(2H)benzopyran-2-one, di-acetyl-pyrocatechol, pyrocatechol-metallyl-ether, 2,2,h-trimethyl-5-hydroxy-(2, 4 )-chromene, 2,2,4-
A 3728-91-KY trimethyl-7-hydroxy-(2,4)-chromene and optionally microelements and/or mesoalements were used.
Among the compounds compensating the unfavourable activity of 2-chloroethyl phosphonic acid 4-methyl-7-hydroxy (2H)-benzopyran-2-one was mentioned, which decreases the intensity of the growth of e.g. the dicotyledonous Chenopodium murale and in other cases when combined with 2-chloroethyl phosphonic acid it increases the crop of the sunflower.
Disclosure of the invention
The present invention is aimed at searching such active ingredients for the treatment of field plants, the use of which makes unnecessary the use of active ingredients which are foreign to the structure of compounds in the plant tissue, such as 2- chloro-ethyl-phosphonic acid, and whereby the loading of the environment and the soil with chemicals can be avoided.
The present invention is related to controlling the growth of field plants, mainly cereals, maize soya and sunflower and the process can be characterized by treating the plants at vegetativ stage, in case of cereals when growing into bush or at 2 nodes stage at the beginning of earing, in maize at 5-8 leaves stage, in soya on the 4-6. week after emergence at a rate of 0.025 to 2.0 kg/ha with a 4-methyl-7-hydroxy[2H]benzopyran-2-one (4-methyl- umbelliferon) of the general formula (I)
Figure imgf000004_0001
or a derivative thereof wherein
R stands for methyl, ethyl, isopropyl , acetyl, chloro-acetyl, propynyl or Cu-, Ni-, Co-, Na- or H- and optionally at a rate of 58 - 117 g metal ion/ha with micro and meso elements, such as boron, magnesium, copper and zinc in the form of water soluble salts and chelates respectively thereof. The effect of the treatment results in a significant increase of the crops both in monocotyledonous and dicotyledonous field plants already by using a relatively small dosis.
The present invention also provides compositions suitable for the treatment of field plants containing in an amount of 1-60 percent by weight a compound of the general formula (l) - wherein the definition of R is as given above - and optionally in the form of water soluble salts or soluble chelates boron, magnesium, copper, zinc as well as solid or liquid carriers, optionally surfactants. The compositions of the invention contain 0.01 - 0. 625 parts of copper, 0.0075 - 0.83 parts of zinc, 0.01 - 0.65 parts of magnesium and 0.00175 - 0.28 parts of boron as microelement in the form of water soluble salts or chelates calculated on metal ion and related to 1 part of the compound of the general formula (I),
The compositions are preferably used in the form of tank mixtures in diluted state and if desired the active ingredients are combined prior to use in the tank mixture.
The compounds of the general formula (I) are known.
4-methyl-7-hydroxy [2H] benzopyran-2-on can be prepared from aceto acetic acid ester and from resorcinol in the presence of an acidic catalyst by
Pechmann condensation [(Org. Synth. Coll. Vol. III.
281-283 p; John Wiley 1955 New York)] . Melting point of the compound is 194 - 195 ºC, UVmax in methanol
221-251, 322,5 nm.
Data of the derivatives are as follows:
Compound of the general formula (I)
Figure imgf000006_0001
C10H7NaO3 2H2O 3300 3080 1735 1610
3010 1720 1590
C20H14CuO6 5H2O 3450 3080 1710 1600
3010 1690 1670
C20H14NiO6 3H2O 3450 3080 1710 1600
3010 1690 1678
C20H14CoO6 3H2O 3300 3080 1725 1610
3010 1703 1600 1690
R = acetyl melting point: 150-151 ºC
R = propynyl melting point: 138 ºC We have found that the use of the benzopyran derivatives of the general formula (I) is advantageous due to the structure being very similar to the structure of the other aromatic ompounds having phenyl-propane sceleton such as coumarin, esculetin, scopoletin and lignine which can be found in bound form in the tissues of the plants. The active ingredients according to the invention can be considered being analogous with those compounds which are synthetized in the plants and thereby neither the soil, nor the plants are loaded with chemicals which cannot be found in the nature. It is also favourable that the compounds of the general formula (I) can be used at a relatively low rate, such as 50 - 500 g/ha, On the other hand, the compounds of the general formula are not toxic to humans or warm blooded animals and can be thus used as pharmaceuticals in human therapy. The active ingredients according to the invention have a further advantage that they do not influence the endogen hormone synthesis in the plants and their effect is presumably due to the fact that they promote the release of indolyl acetic acid synthetized by the plants but being in bound form.
Compounds according to the invention are applied in the form of dusting agents, wettable powders or emulsifiable concentrates, which can contain solid or liquid carriers and/or surfactants.
Among solid carriers kaolin, bentonite, silicic acid, dolomite, calcium carbonate, talc, and among liquid carriers aliphatic, aromatic, cycloaromatic solvents, mineral oil fractions and alcohols can be mentioned. Surfactants can be non-ionic and anionic, as anionic surfactants salts of aliphatic sulfonic acid esters, salts of aromatic sulfonated compounds, alkali salts of lignosulfonate and as non-ionic surfactants fatty alcohol derivatives of ethylene oxide or propylene oxide, alkyl phenols, oils or fats can be employed. The compositions in concentrated form are diluted prior to use to 0.01 - 4-5 % by weight sprayable compositions. The usual dosis of the compositions is 0.025 - 2.0 kg per hectare, but higher dosis may be used as well for special purposes.
The compositions according to the invention are suitable for the treatment of monocotyledonous and dicotyledonous field plants, such as cereals, maize, sunflower, cole-seed, sugar beet and soya. Micro- and mesoelements are usually used in the form chelates. As chelate forming agent K-p- phenol-lignosulfonate can be used. As chelates magnesium chelate at a concentrat ion of 40 g/l, copper chelate at a concentration of 40 g/l, zinc chelate at a concentration of 30 g/l can be mentioned. The preparation of the chelates as well as the details of the preparation of the compositions according to the invention can be found in the following examples.
Example 1 % by weight
4-methyl-7-hydroxy[2H]behzopyran-2-one 60 sodium salt of lignine sulfonic acid 4 fatty alcohol sulfonate 4 colloidal synthetic silicium-dioxide 20 kaolin 12
Example 2 25 g of 4-methyl-umb elliferon are admixed with the sodium salt of 3 g diisobutyl-naphtalene-sulphonic acid, 5 g of the sodium salt of lignine sulphonic acid and with 67 g of kaolin. The mixture is ground and wettable powder is obtained.
Example 3
10 g of 4-methyl-umbelliferon are dissolved in a mixture of 56 g dimethyl-formamide and 14 g of xylol and an addition product of 40 mol of ethylene- oxide and 1 mol of lauryl acid in an amount of 20 g is added. The composition is diluted with water prior to use to the desired concentration.
Example 4
% by weight 4-methyl-7-hydroxy[2H]benzop ran-2-one 5.5 fatty alcohol-sulfonate 5.0 colloidal-synthetic silicium-dioxide 30.0 kaolin 54.5
Example 5
20 g of sodium salt of 4-methyl-7-hydroxy- [2H]benzopyran-2-one are dissolved in 70 ml of water and to the solution 5 g of iso-tridecyl-alcohol-poly-ethyleneglycol-ethe r are added as surfactant. The composition is then diluted with water to 100 ml.
Example 6
20 g of isopropyl-amine salt of 4-methyl-7- hydroxy (2H) benzopyran-2-one is dissolved in 70 ml of water and as a surfactant 5 g of isotridecyl- alcohol-polyethyleneglycol-ether are added and the composition is diluted with water to 100 ml.
Example 7
Micro- and mesoelement compositions are prepared as follows:
The used compositions are prepared from water soluble salts and chelate forming agents so that one liter of the solution contains the given amount of ions. As chelate forming agent trimethyl-diamine- 2,2'-hydroxy-5,5'-potassium-potasslum-para-phenol- sulfonate is used.
The salts and chelate forming agents are dissolved in a necessary amount of water and the volume of the solution is completed with water to 1 liter. a) Copper complex solution (40 g/liter copper- ion concentration)
157.2 g crystalline copper sulfate and 156 g chelate forming agent are dissolved in water and the volume is completed with water to 1 liter. b) Zinc-complex solution ( 30 g/liter zinc-ion concentration) 62.5 g zinc-chloride and
227 g chelate-forming agent are dissolved in water and the volume is completed with water to 1 liter. c) Magnesium-complex solution (40 g/liter magnesium ion concentration)
234.3 g of crystalline magnesium acetate and
407 g of chelate-forming agent are dissolved in water and the volume is completed with water to 1 liter. d) Boron-solution (7 g/liter boron-ion concentration)
40 g of ortho tartaric acid are dissolved in water and the volume is completed with water to 1 liter.
Example 8 % by weight
4-methyl-7-hydroχy[2H] benzopyran-2-one 1 alkylphenol-alkoxylate (Emulsogen ICL) 5 xylol 94
Biological activity
The tests were performed on field cernozjom soil on 2x10 m2 plots in 4 repetitions by using winter wheat, maize, soya, and sunflower indicating plants. The spray-liquid was sprayed by using a plot spraying machine of the type Patox 20. Amount of spray liquid: 220 l/ha.
The following composition was used for the test:
% by weight 4-methyl-7-hydroxy[2H]benzopyran-2-on 60 sodium-lignin-sulf onate 4 fatty alcohol 4 colloidal synthetic silicium-dioxide 20 kaolin 12
Micro- and mesoelements were used as disclosed in Example 7.
Example 9
Test plant : sunflower
Art : Marianne
Stock number: 62 thousand stocks/ha
Sowing: April 17th Harvest: September 25th
Weed-killing: 910 g/ha 2,6-dinitro-N,N-dipropyl-4- trifluoro-methyl-aniline + 1250 g/ha
N-(4-bromo-3-chloro-phenyl)-N'- methoxy-N-methyl-urea Chemical fertilizer: NH4NO3 = 120 kg/ha
P2O5 = 150 kg/ha
K2O = 200 kg/ha
Time of treatment : in 2-6 pairs of leaf stage of the plants Compositions and dosis: 4-methyl-7-hydroxy[2H]benzo- pyran-2-one 62.5 g/ha
125.0 g/ha
250.0 g/ha microelements: 0.5-0.5 l/ha in the form of the compositions according to Example 7 Concentration of spray-liquid: 0.028-0.23 % by weight volume related to the active ingredient.
Treatment, dosis Crop t/ha %
Figure imgf000012_0001
g/ha, l/ha I. ll. llI. IV. Average
1) Control 1.96 2.13 1.87 2.26 2.06 100
2) 4-methyl-umbel- liferon
62.5 g/ha 2.14 2.26 1.97 2.35 2.18 106
3) 4-methyl-umbel- liferon
125 e/ha 2.47 2.31 2.53 2.28 2.40 116
4) 4-methyl-umbel- liferon
250 g/ha 2.69 2.74 2.48 2.57 2.62 127
5) Zn-, Cu-, B-, Mg-chelate
0.5-0.5 l/ha
Figure imgf000012_0003
2.11 2.00 2.24 2.05 2.10 102
6) 4-methyl-umbel- liferon
62.5 g/ha +
Zn-, Cu-, B-,
Mg-chelate
Figure imgf000012_0002
0.5-0.5 l/ha 2.29 2.36 2.19 2.41 2.31 112
7) 4-methyl-umbel- liferon
125 g/ha +
Zn-, Cu-, Mg-,
B-chelate
Figure imgf000012_0004
0.5-0.5 l/ha 2.39 2.66 2.47 2.51 2.50 122
8) 4-methyl-umbel- liferon
250 g/ha +
Zn- , Cu- , Mg- ,
B-chelat e
0. 5-0. 5 l/haX
Figure imgf000012_0005
2. 71 2. 62 2. 80 2. 57 2. 67 130
x = Composition according to Example 7 According to the test results 4-methyl-7- hydroxy[2H]benzopyran-2-one increased the sunflower crop at a very low doses (62.5 g/ha). Increase: 6 % . By increasing the rate to 250 g/ha the crop increase was 27 % . By using 4-methyl-7-hydroxy[2H]benzopyran-2-one together with the micro elements of the invention the crop increase was higher, particularly when using smaller rates of 4-methyl-7-hydroxy[2H]benzo-pyrane-2-one ( 62.5-125g/ha).
Example 10 Test plant : soya Art : Merit
Stock number: 575 thousand stocks/ha Sowing: April 25th
Harvest : October l6th
Weed-killing: 910 g/ha 2,6-dinitro-N,N-dipropyl-4- trifluoro-methyl-aniline + 1690 g/ha 3-isopropyl-1,2,3-benzothio-diazinon- (4)-2,2-dioxide
Chemical fertilizer: NH4NO3 = 50 kg/ha
P2O5 = 130 kg/ha K2O = 165 kg/ha Time of treatment : before the appearance of flower buds.
Compositions and dosis: 4-methyl-7-hydroxy[2H] benzo- pyran-2-one 250 g/ha 500 g/ha 1000 g/ha microelements: 1.0-1.0 l/ha from the composition according to Example 7. Concentration of spray liquid: 0.11-0.68 % by weight /volume related to the active ingredient. Treatment, dosis Crop t/ha %
Figure imgf000014_0001
g/ha, l/ha II. III. IV. Average
1) Control 2.75 2.45 2.50 2.70 2.60 100
2) 4-methyl-umbel- liferon
250 g/ha 2.78 2.96 2.86 2.92 2.88 111
3) 4-me thyl-umbel- liferon 500 g/ha 2.75 2.72 2.69 2.48 2.66 102
4) 4-methyl-umbel- liferon 1000 g/ha 2.66 2.57 2.63 2.55 2.60 100
5) Zn-, Cu-, B-, Mg-chelate
Figure imgf000014_0004
1.0-1.0 l/ha 2.57 2.78 2.43 2.85 2.66 102
6) 4-methy1-umbel- liferon
250 g/ha +
Zn-, Cu-, B-,
Mg-chalafee
1-1 l/has 3.05 2.90 3.17 2.88 3.00 115
7) 4-methyl-umbel- liferon
500 g/ha +
Zn-, Cu-, B-,
Mg-chela
Figure imgf000014_0003
te
1-1 l/haS 2.77 2.85 2.80 2.81 2.81 108
8) 4-methy1-umbel- liferon
1000 g/ha +
Zn-, Cu-, B-,
Mg-chela
Figure imgf000014_0002
te
1-1 l/hax 2.67 2.81 2.56 2.83 2.72 105
x composition according to Example 7.
The crop of soya was increased at the highest extents (11-15 %), when using the lowest examined doses (250 g/ha) of 4-methyl-7-hydroxy[2H]benzopyran-2-one alone and also when completed with micro elements. By increasing the doses the efficacy of 4-methyl-7- hydroxy[2H]benzopyran-2-one decreased. Example 11 Test plant: winter wheat Art : Mv-8
Sowing: October 5th Harvest : July 25th
Stock number: 6.5 million/ha
Weed-killing: ammonium salt of 2, 4-dichloro-phenoxy- acetic acid 1.12 kg/ha Chemical fertilizer: NH4NO3 = 200 kg/ha
P2O5 = 120 kg/ha K2O = 140 kg/ha Time of treatment: growing into bush, respectively, at the start of earing Compositions and dose: 4-methyl-7-hydroxy[2H] benzopyran- 2-one
500 g/ha 1000 g/ha when growing into bush 2000 g/ha 25 g/ha
50 g/ha at the start of earing 100 g/ha microelements: 1.0-1.0 l/ha from the composition according to Example 7.
Concentration of spray-liquid: 0.011-1.13 % by weight/ volume related to the active ingredient.
Treatment, dosis Crop t/ha % g/ha, l/ha
Figure imgf000015_0001
I. ll. ll l. lv. Average
1) Control 7.44 8.12 7.75 7.-67 7.75 100
Growing into bush Treatment, dosis Crop t/ha % g/ha, l/ha
Figure imgf000016_0001
l. II. III. IV. Average
2) 4-methyl-umbel- liferon 500 g/ha 8.34 8.29 8.76 8.67 8.52 110
3) 4-methyl-umbel- liferon 1000 g/ha 8.65 9.06 8.74 8.81 8.82 114
4) 4-methyl-umbel- liferon 2000 g/ha 8.58 8.50 8.82 8.56 8.62 111
5) Un-, Cu-, B-, Mg-chelate 1-1 l/ha 7.81 8.01 7.79 7.97 7.90 102
6) 4-methyl-umbel- liferon
500 g/ha +
Zn-, Cu-, D-,
Mg-chelate
1-1 l/ha 9.17 9.16 8.85 9.05 9.06 117
7) 4-methyl-umbel- liferon
1000 g/ha +
Zn-, Cu-, B-,
Mg-chelate
1-1 l/ha 8.87 8.60 8.47 8.60 8.64 111
8) 4-methyl-umbel- liferon 2000 g/ha + Zn-, Cu-, B-, Mg-chelate 1-1 l/ha 8.82 8.64 8.48 8.70 8.66 111
Start of earing
9) 4-methy1-umbel- liferon 25 g/ha 8.07 7.95 8.11 8.16 8.07 104
10) 4-methyl-umbel- liferon 50 g/ha 8.39 8.41 8.52 8.43 8.44 109
11) 4-methyl-umbel- liferon 100 g/ha 8.33 8.50 8.54 8.46 8.46 109 Treatment, dosis Crop t/ha % g/ha, l/ha'
I. II. III. IV. Average
12) Zn-, Cu-, B-, Mg-chelate
0.5-0.5 l/ha 8.00 7.83 8.02 8.11 7.99 103
13) 4-methyl-umbel- liferon
25 g/ha +
Zn-, Cu-, B-,
Mg-chelate
0.5-0.5 l/ha 8.17 8.22 8.06 8.25 8.18 105
14) 4-methyl-umbel- liferon
50 g/ha +
Zn-, Cu-, B-,
Mg-chelate
0.5-0.5 l/ha 8.53 8.62 8.49 8.70 8.59 111
15) 4-methyl-umbel- liferon
100 g/ha +
Zn-, Cu-, B-,
Mg-chelate
0.5-0.5 l/ha 8.64 8.70 8.51 8.69 8,64 111
= Composition according to Example 7.
When using 4-methyl-7-hydroxy[2H] benzopyran-2- one at two different stages of development of winter wheat a crop increase over 10 % or almost 10 % can be achieved when using the substance alone by spraying it on the plants at a rate of 500 - 1000 g/ha when growing into bush, and at a rate of 50 - 100 g/ha at the start of earing.
When completed 4-methyl-7-hydroxy[2H]benzo-pyran-2-one with microelements a 17 % crop increase was observed at a rate of 500 g/ha when growing into bush.
The treatment at the stage of earing with the combination resulted in a 11 % crcp increase when the compounds was used at a rate of 50 g/ha completed with micro elements.
Example 12 Test-plant: maize Art: Pi-3709 Sowing: April 28. Harvest: November 16. Stook-number: 82.500 stock/ha Weed-killing: N,N-d i-n-propyl-S-ethy l-thiocarbamate
500 g/ha + N-(3,4-dichloro-phenyl)-N'- methyl-urea 1250 g/ha Chemical fertilizer: NH4NO3 = 270 kg/ha
P2O5 = 150 kg/ha K2O = 200 kg/ha
Time of treatment: in 6-8 leaves stage of the plantsCompositions and dosis: 4-methyl-7-hydroxy[2H]benzo- pyran -2-one 250 g/ha
500 g/ha 1000 g/ha microelements: 1.0-1.0 l/ha from the compositions according to Example 7 Spray liquid concentration: 0.22-1.13 % by weight/ volume related to the active ingredient.
Treatment, dosis Crop t/ha % g/ha, l/has I. II. III. IV. Average
1) Control 10.7 10.2 10.9 10.4 10.6 100
2) 4-methyl-umbel- liferon
250 g/ha 12.9 13.1 12.5 12.0 12.6 119 Treatment, dosis Crop t/ha %
Figure imgf000019_0005
g/ha, l/ha I. II. III. lV. Average
3) 4-methyl-umbel- liferon
500 g/ha 12.1 12.4 12.3 11.8 12.2 115
4) 4-methyl-umbel- liferon
1000 g/ha 11.8 12.3 .11.5 12.0 11.9 112
5) Zn-, Cu-, Mg-, B-chelate
1-1 l/ha X
Figure imgf000019_0001
11.2 10.9 11.6 11.0 11.2 105
6) 4-methy1-umbel- liferon 250 g/ha + Zn-, Cu-, Mg-,
B-chelate 1-1 l/ha*
Figure imgf000019_0002
12.6 13.9 13.4 14.1 13.5 127
7) 4-methyl-umbel- liferon
500 g/ha +
Zn-, Cu-, Mg-,
B-chelate
1-1 l/haS
Figure imgf000019_0003
13.8 14.2 13.1 13.3 13.6 128
8) 4-methyl-urabel- liferon
1000 g/ha + Zn-, Cu-, Mg-,
B-chelate 1-1 l/haS
Figure imgf000019_0004
. 12.7 13.1 12.2 12.5 12.6 119
= Composition according to Example 7
Related to the untreated control 4-methyl-7- hydroxy[2H]benzopyran -2-one increased the crop by 19 % when used at a rate of 250 g/ha.
By increasing of the dosis the extent of growth was only 12-15 %.
When completed with micro elementes 4-methyl- 7-hydroxy[2H]benzopyran -2-one resulted a crop increase of 27-28 ia on using a lower dosis pro hectar.

Claims

Claims
1. Composition suitable for the treatment of field plants, mainly for regulating the growth of cereals, soya, maize or sunflower at their vegetative or generative stage of development which comprises containing in a total amount of l-60 % by weight 1 part by weight of 4-methyl-7- hydroxy-[2H]benzopyran-2-one or a derivative of the general formula
Figure imgf000020_0001
- wherein
R stands for methyl, ethyl, isopropyl, acetyl, chloro-acetyl, propynyl or Cu-, Ni-, Co-,
Na- or H - and optionally in the form of soluble salts or chelates - related to the metal ion - 0.00175 - 0.28 parts by weight of boron, 0.01 - 0.625 parts by weight of magnesium, 0.01 - 0.625 parts by weight of copper and 0.0075 - 0.83 parts by weight of zinc.
2. Process for treating field plants, mainly cereals, soya, maize or sunflower which comprises treating the plants in the vegetative or generative stage of development, preferably when growing in to bush or at the start of earing of the cereals, at 5-8 leaves stage of maize, at 2-6 pairs of leaf of sunflower and 4-6 weeks after emergence of soya at a rate of 0.025 - 2.0 kg/ha with 4-methyl-7-hydroxy-[2H]benzopyran-2-one or a derivative thereof of the general formula
Figure imgf000021_0001
- wherein R stands for methyl,, ethyl, isopropyl, acetyl, chloro-acetyl, propynyl or Cu-, Ni-, Co-, Na- or H - and optionally simultaneously or previously at a rate of of 58 - 117 g metal ion per hectare with spray liquids containing magnesium, copper, zinc and boron in the form of metal chelates or water soluble salts.
PCT/HU1986/000013 1985-03-04 1986-03-04 Composition and process for the preparation of field plants WO1986005069A1 (en)

Priority Applications (1)

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DK523586A DK523586A (en) 1985-03-04 1986-11-03 METHOD AND PROCEDURE FOR TREATMENT OF MARKET PLANTS

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HU78285A HU192678B (en) 1985-03-04 1985-03-04 Composition and process for treating field plants

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0694257A1 (en) * 1994-07-25 1996-01-31 American Cyanamid Company 4-Phenoxycoumarins and thio derivatives thereof, their preparation and use as herbicides

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1984003418A1 (en) * 1983-03-08 1984-09-13 Nitrokemia Ipartelepek Process and composition for plant growth regulation

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1984003418A1 (en) * 1983-03-08 1984-09-13 Nitrokemia Ipartelepek Process and composition for plant growth regulation

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Chemical Abstracts, vol. 79, issued 1971,November 12 (Columbus, Ohio, USA) S.a.Vichkonova et al. "Antimicrobial and antiviral acitivity of some natural coumarins", see page 49, column 1, abstract-no. 111980v, Rast. Resur. 1973,9(3), 370-9 (Russ),(Section 3). *
Rompps Chemie-Lexikon, 7th edition, vol. 5, issued 1972 (Francksche Verlagshandlung Stuttgart), see pages 3299-3301, especially page 3300, left column, lines 19-33. *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0694257A1 (en) * 1994-07-25 1996-01-31 American Cyanamid Company 4-Phenoxycoumarins and thio derivatives thereof, their preparation and use as herbicides

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DK523586D0 (en) 1986-11-03
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DK523586A (en) 1986-11-03
JPS62501975A (en) 1987-08-06
EP0215092A1 (en) 1987-03-25

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