COMPOSITION AND PROCESS FOR THE PREPARATION OF FIELD PLANTS

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-[2H]benzopyran-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 5 and process for the treatment of field plants in order to intensify the plant growth. Technical Field Q • When growing field plan ' bs 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 5 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 0 plant growth, withering and necrotic symptoms may occur instead of the expected favourable effect. Background Art 5 n order to compensate a possible unfavourable effect of 2-chloroethyl phosphonic acid in the vegeta¬ tive 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- 0 -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, -π_ethyl-7-hydroxy-( 2H) benzo yran-2-one, di- 5 acetyl-pyrocatechol, pyrocatechol-metallyl-ethe , 2,2, h-trimethyl-5-.hydroxy_( 2; )-chromene, 2,2,-+- A 3728-91-KY < fau>__. trimethyl-7-hydroxy-( 2,4) -chromene and optionally microelements and/or mesoalements were used. Among the compounds compensating the un¬ favourable activity of 2-chloroethyl phosphonic acid 4-methyl-7-hydroxy ( H) -benzopyran-2-one was men¬ tioned, which decreases the intensity of the growth of e.g. the dicotyledonous Che opodium rrrurale and in other cases when combined with 2-chloroethyl phosphonic acid it increases the crop of the sun¬ flower. 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 struc¬ ture of compounds in the plant tissue, such as" 2- -chloro-ethyl-phosphonic acid, and whereby the load¬ ing of the environment and the soil with chemicals can be avoided. The present invention is related to controll¬ ing 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 no es 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 [2H3 benzopyran-2-one (4-methyl- -umbelli eron) of the general formula (I) 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, mag¬ nesium, copper and zinc in the form of water soluble salts and chelates respectively thereof. The effect 10 of the treatment results in a significant increase of the orops both in monocotyledonous and dicotyle¬ donous field plants already by using a relatively small dosis. The present invention also provides composi- 15 tions 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 •20 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 2o 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 fo-rm of tank mixtures in diluted state and if 3 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 [2Hl benzopyran-2-on can be 35 prepared from aceto acetic acid ester and from resorcinol in the presence of an acidic catalyst by Pechmann condensation C(θrg. Synth. Coll. Vol. III. 281-283 p; John Wiley 1955 New York)] . Melting point of the compound is 194 - 195 C, UVmax in methanol 221-251, 322,5 nm. Data of the derivatives are as follows : Compound of the general formula (I) C=C C 1(- H 7 Na0 3 2H 2 0 3300 3080 1735 1610 3010 1720 1590 C 20 H 14 Cli0 6 5H 2 0 3k 50 3080 1710 1600 3010 1690 1670 C 20 H 14 Ni °6 3H 2 o 3450 3080 1710 • 1600 3010 1690 1678 C 20 H 14 CO °6 3H 2 0 3300 3080 1725 1610 3010 1703 1600 1690 R = acetyl melting point : I5O-I5I C R = propynyl melting point : 138 C tf θ 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 hD__mone 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 re applied in the form of dusting agents, wettable powders or emulsifiable concentrates, which can con¬ tain 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 sur- factants 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 % b weight sprayable compositions. The usual dosis of the com- positions 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 -p- -phenol-lignosulfonate can be used. As chelates magnesium chelate at a concentration 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 composi¬ tions according to the invention can be- found in the following examples. Example 1 fo by weight 4-methyl-7-hydroxy [2__Q behzopyran-2-one 6θ 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-umbelliferon are admixed with the sodium salt of 3 g diisobutyl-naphtalene- -sulphonic acid, 5 S °f "fc-nβ 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 dimethy1-formamide and 14 g of xylol and an addition product of 40 mol of ethylene- -αxide 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-π_ethyl-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-π_ethyl-7-hydroxy- [2H] benzopyran-2-one are dissolved in 70 ml of water and to the solution 5 S °f iso-tridecyl-alcohol-poly- ethyleneglycol-ethe 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 S °f isotridecyl- -alcohol-polyethyleneglycol-ether are added and the composition is diluted with water to 100 ml. Example 7 Micro- and mesoelement compositions are pre¬ pared 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 trimethy1-diamine- -2, 2' -hydroxy-5, 5'-potassium-potasslum-pa a-phenol- -sulfonate is used. The salts and chelate forming agents are dis- solved 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 S zinc-chloride and 227 g chelate-forming agent are dissolved in water and the volume is co-mpleted 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 concentra¬ tion) 40 g of ortho tartaric acid are dissolved in water and the volume is completed with water to 1 liter. Example 8 o by weight 4-methyl-7-hydroχy[2Hl benzopyran-2-one 1 alkylphenol-alkoxylate (Emulsogen ICL) 5 xylol 94 Biological activity The tests were performed on field cernozjom 2 soil on 2x10 m 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 5 test: by weight 4-methyl-7-hydroxy [2H3 benzopyran-2-on 6θ sodium-lignin-sulfonate 4 fatty alcohol 4 0 colloidal synthetic silicium-dioxide 20 kaolin 12 Micro- and mesoelements were used as dis¬ closed in Example 7. 5 Example 9 Test plant : sunflower Art : Marianne Stock number: 62 thousand stocks/ha Sowing: April 17th 20 Harvest: September 5th Weed-killing: 910 g/ha 2, 6-dinitro-N,N-dipropyl-4- -trifluoro-me hyl-aniline + 1250 g/ha N-(4-bromo-3-chloro-phenyl) -N' - -methoxy-N-methyl-urea 25 Chemical fertilizer: Time of treatment : i stage of the plants 30 Compositions and dosis: 4-methyl-7-hydroxy " [2H1 benzo- pyran-2-one 62.5 g/ha microelements: 0.5-0.5 l/ha 3.3 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 s g /ha, l/ha Iβ TL HI. IV. Aver ¬ age 1) Control 1.96 2.13 1 * 87 2.26 2.06 100 2) 4-methyl-umbel- liferon 62.5 g/ka 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 O.5-O.5 l/ha 2.11 2.00 2.24 2.05 2.10 102 6) 4-methyl-umbel- liferon 62.5 e/ha + Zn-, Cu-, B-, Mg-chelate O.5-O.5 l/ha K 2.29 2.36 2.19 2.41 2.31 112 7) 4-methyl-umbel- liferon 125 g/ha + Zn-, Cu-, Mg-, B-chelate O.5-O.5 l/ha x 2.39 2.66 2.47 2.51 2.50 122 8) 4-methyl-umbel- liferon 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 sun lower crop at a very low doses (62.5 g/ha). Increase: 6 o . By increasing the rate to 250 g/ha the crop increase was 27 i°. By using 4-methyl-7-hydroxy [2Efl benzopyran -2-one together with the micro elements of the inven¬ tion the crop increase was higher, particularly when using smaller rates of 4-πiθthyl-7-hydroχy [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-isopro * pyl-l,2, 3-benzothio-diazinon- -(4)-2,2-dioχide Chemical fertilizer: Time of treatment : before the appearance of flower buds. Compositions and dosis: 4-methyl-7-hydroxy [2H] benzo- pyran-2-one 250 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 o by weight /volume related to the active ingredient. Treatment, dosis Crop t/ha x ■ 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-methyl-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 1.0-1.0 l/ha 2.57 2.78 2.43 2.85 2.66 102 6) 4-methy1-umbel- liferon 3 ' .05- 2.90 3-17 - 2.88 3.00 115 7) 4-methyl-umbel- liferon 500 g/ha + Zn-, Cu-, B-, Mg-chelate 1-1 l/ha S 2.77 2.85 2.80 2.81 2.81 108 8) 4-methy1-umbel- liferon 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 ( H-15 <f 0 ) , when using the lowest examined doses (250 g/ha) of 4-methyl-7-hydroxy [2H1 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 Chemical fertilizer: 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 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 If τχ ^ --- ^ χv^ Averagβ 1) Control 7.44 8.12 7.75 7.-67 7.75 100 Growing into bush Treatmen , dosis Crop t/ha g/ha, l/ha - II. III. IV. Average 2) 4-methyl-umbel- liferon 500 g/ha • 8.34 8.29 8.76 8.67 8.52 liυ 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 9.17 9.16 8.85 9-05 9.06 117 7) l- 8.87 8.60 8.47 8.60 8.64 111 8) 4-methyl-umbel- liferon 8.82 8.64 8.48 8.70 8.66 111 Start of earing 9) -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 reatment, dosis Crop t/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 8.17 8.22 8.0c 8.25 §..18 105 14) 4-methyl-umbel- liferon 8.53 8.62 8.49 8.70 8.59 111 15) 4-methyl-umbel- liferon 100 g/ha + Zn-, Cu-, B-, Mg-chelate O.5-O.5 l/ha 8.64 8.70 8.51 8.69 8,64 111 x = 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 o 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 crop increase when the compounds was used at a rate of 50 g/ha completed with micro elements. Example 12 5 Test-plant: maize Art: Pi-3709 Sowing: April 28. Harvest: November 16. Stook- umbe : 82.500 stock/ha 10 Weed-killing: N,N- i-ti-propyl-S-ethy -thiocarbamate 500 g/ha + N-(3,*+-dichloro-phenyl)-N'- -methyl-urea 1250 g/ha Time of treatment: in 6-8 leaves stage of the plants .Compositions and dosis: 4-methyl-7-hydroxy[2H]benzo- pyran -2-one 250 g/ha microelements: 1.0-1.0 l/ha from the compositions accord¬ ing to Example 7 Spray liquid concentration: 0.22-1.13 by weight/ 5 volume related to the active ingredient. Treatment, dosis Crop t/ha g/ha, l/ha s I. II. III. IV. Average 0 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 5 Treatment, dosis Crop t/ha £ g/ha, l/ha I. II. III. rv. 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 11.2 10.9 11.6 11.0 11.2 105 6) 4-methy1-umbel- Liferoα B che ate 1-1 l/ha* 12.6 13.9 13.^ 1^.1 13.5 127 7) 4-methyl-umbel- li eron 13.8 14.2 13.1 13*3 13.6 128 8) 4-methyl-urabel- liferon 12.7 13.1 12.2 12.5 12.6 119 x = Composition according to Example 7 Related to the untreated control 4-methyl-7- -hydroxy[2H]benzopyra — 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 in¬ crease 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-6θ by weight 1 part by weight of 4-methyl-7- -hydroxy-[2H]benzopyran-2-one or a derivative of the general formula - 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 sun lower 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 - wherein R stands for methyl,, ethyl, isopropyl, acetyl, chloro-acetyl, propynyl or Cu- , i** , 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.

Inventors: BALINT SANDOR, BENCZIK JUDIT, FODOR FERENC, GAAL SANDOR, GARDI IVAN, HORVATH ANDRAS, KARACSONYI BELA, KARSAI JOZSEF, SEBESTYEN ENDRE, SIKI KAROLY, SOEPTEI CSABA, TOEMOERDI ELEMER, ZBISKO LASZLO, BALINT, SANDOR, BENCZIK, JUDIT, FODOR, FERENC, GAAL, SANDOR, GARDI, IVAN, HORVATH, ANDRAS, KARACSONYI, BELA, KARSAI, JOZSEF, SEBESTYEN, ENDRE, SIKI, KAROLY, SOEPTEI, CSABA, TOEMOERDI, ELEMER, ZBISKO, LASZLO
Applicants: NITROKEMIA IPARTELEPEK
Application year: 1986
Main classification: A01N43
IPC codes: A01N43, A01N55, A01N59