NEW SUCCINIC ACID DERIVATIVES, PLANT GROWTH REGULATING COMPOSITIONS CONTAINING THEM AND A PROCESS FOR THE PREPARATION THEREOF

Abstract: New succinic acid derivatives of general formula (I) wherein A represents hydrogen, a naphthoxyethyl group of formula (b), or a substituted phenoxyethyl group of general formula (a), and in this latter formula R stands for hydrogen or C1-4 alkyl, R<1> is hydrogen, halo or C1-4 alkyl, and R<2> and R<3> each stand for hydrogen or halo, and agriculturally acceptable salts thereof are prepared by reacting succinic anhydride with an aryloxyethanol of the general formula (III). The new succinic acid derivatives of general formula (I) possess plant growth regulating properties.

Description: NEW SUCCINIC ACID DERIVATIVES , PLANT GROWTH REGULATING COMPO TIONS CONTAINING THEM AND- A PROCESS FOR THE PREPARATION THER The invention rela tes to new mono- or di- (arylo__:y ethyl) -succinates and plant growth, regulating compositions containing these compounds . The invention also relates to process for the prepara tion of new mono- or di-(aryloxyethyl succinates . Succinic a cid-2, 2 -dime hyl -hydra zide (da inozide) is a well known compound utilized as active ingredient in plant growth regulating compositions (Alar-85 WP; see : Louis G. Nickall : Plant Growth Regulators Agricultural Uses ; Springer Vβrlag, Berlin-He idelberg-New York, 1982) . British patent specification No . 1, 91,308 discloses various β-phenoxyethyl and β-phenylthioethyl carboxylates a fungicides ; one of them being β-phenoxyeth l succinate . Now it has been found that certain mono- and di-(ary • oxyethyl) succina tes and agriculturally acceptable salts thereof possess excellent plant growth regula ting propertie superior to those of the known substances of rela ted structu Based on the above , the invention rela tes to mono- and di-(aryloxyethyl) succina te s of the general formula (I) , wherein A represents hydrogen, a naphthoxyethyl group of formula (b) or a substituted phenoxyethyl group of the general formula (a) , and in this la tter formula R stands for hydrogen or C, ^ alkyl, R is hydrogen, halo or C^^ alkyl , and R and each stand for hydrogen or halo , with the proviso that at least one of the two A groups is other than hydrogen, and agriculturally acceptable salts thereof. The invention also relates to agricultural, primarily plant growth regulating compositions, comprising as active agent at least one compound of the general formula (I). In the above formula the term "alkyl" means preferably methyl, whereas "halo" means preferably chloro. Substituents R 1 , R 2 and ^ 3 are attached to the phenyl ring preferably in positions 2 and/ or 4- and/or 5 » The invention also rela tes to a proce ss for the pre pa tion of compounds having the genera l formula ( I) wi th the ex ception of β-phenoxye hyl succina te . The compounds of the general formula (I) are pre pared according to the invention by reacting succinic anhydride of formula (II) 0 0H - C . I 2 (II) σΞ 2 - < ° with an aryloxy ethanol of the general formula (III) , R HO - CHg - CH - 0 - A (III) wherein A is as defined above . Depending on whether a mono or a die ster is required, the alcohol of the general formula ( III) is utilized in amounts of e ssent ially 1 or 2 molar equivalents . The reac¬ tion is performed in the presence of a mineral acid, such as concentra ted sulfuric acid, as catalyst. The reaction is performed preferably in a solvent, such as in a chlorinated hydrocarbon (e.g. carbon tetrachlor ide) , a ketone (e.g. methyl-ethyl ketone) or in a mixture thereof, .or in an aromatic hydrocarbon (e.g. benzene). Water formed in the diesterification reaction should be removed continuously from. the system e.g. by utilizing a Marcusson apparatus. The reaction temperature may be as high as the boilin point of the mixture. It is preferred to perform the reactio in a refluxing mixture. The resulting product can be separated and, if neces purified by methods known per sβ. The salts of the monoesters may be salts formed with inorganic or organic bases, such as alkali metal salts, alka ine ' earth metal salts or salts formed with organic amines. These salts can be prepared by methods known per se. Depending on whether a mono- or a diestar is to be pre pared, one proceeds e.g. as follows: Succinic anhydride is suspended in carbon tetrachlori or in a mixture of carbon tetrachloride and methyl ethyl ket 1-2 drops of sulfuric acid are added to the suspension, the mixture is heated to reflux temperature, and one molar equi¬ valent of the appropriate aryloxy alcohol of the general formula (III) is added dropwise to the boiling suspension under stirring within one hour. Thereafter the mixture is stirred and refluxed for 1-3 hours. The mixture is allowed t cool, the separated monoester is filtered off, washed with water or aqueous alcohol, and dried at a temperature not ex ceeding 0°C. * When a diester is to be prepared, succinic anhyd 2 molar equivalents of the appropriate aryloxy ethanol and 15-20 drops of sulfuric acid are added to an aromatic solve such as benzene. The mixture is stirred and refluxed for 5 hours in a flask equipped with a Marcusson apparatus. There after the mixture is allowed to cool, the diester is filte off, washed with water, aqueous sodium carbonate solution a then with water again, and dried at a tempera ure not exce ing 40°C. The preparation of the compounds having the gener formula (I) is illustrated in detail in the following Examples. Example 1 (2-Mβtby 1-2-/2* ,4 > .5 , -trichlorophenoxy/-e hyl) succinate 16 g (0.16 mole) of finely powdered succinic an¬ hydride are added to a mixture of 250 ml of dry carbon tetr chloride and 50 ml of methyl ethyl ketone. The mixture is h ed to reflux, and a solution of 40.9 g (0.16 mole) of 2-met 2- (2 , ,4 , ,5*-trichlorophenoxy) -ethanol in 50 ml of methyl ethyl ketone is added dropwise to the stirred mixture withi one hour. Thereafter the mixture is stirred and refluxed fo one hour. The mixture is allowed to cool, the product is filtered off with suction, admixed with about 3 volumes of 80% aqueous ethanol, and filtered. The product is dried at 40°C. 27.2 g (47,8 %) of the title compound are obtained. Example 2 Di-(β-naphthoχyethyl succinate 50 g (0.5 mole) of succinic anhydride, 188 g (1 mo of β-naphthoxy-ethanol and 10 drops of concentrated sulfuri acid are added to 300 ml of dry benzene. The reaction mixtur is stirred and refluxed for 8 hours under a Marcusson water separator. The mixture is allowed to cool, the separated product is filtered off by suction, washed with water, then three times with an aqueous sodium carbonate solution, and finally with water again. The product is dried at room tempe ture. 171 g (74.7 %) of the title compound are obtained. Example 5 Phenoxyethyl succinate 250 g (2.5 moles) of finely powdered succinic anhydr and two drops of concentrated sulfuric acid are added to 300 ml of dry carbon tetrachloride. The mixture is heated to boiling, and then 3 -5 S (2.5 moles) of phenoxyethanol are added dropwise to the stirred mixture within one hour. The resulting mixture is stirred under reflux for one hour, and then allowed to cool. The separated product is filtered off suction, washed with water, and dried at room temperature. 583 g (98 %) of the title compound are obtained. The compounds of the general formula (I) pre _pared according to the invention are summarized in Table I. Table I Compound Characteristic IR No. A R R J R c R' Mp.°C bands, cm""l C=0 (ester) OH (acid) 1 H and (a) H H H H 74- 76 1725 3650-2400 2 H and (a) H CH 3 Cl H • • 81- 82 3 H and (a) CH 5 Cl Cl Cl 160 4 H and (b) - — - - 114-116 5 (a) and (a) H GH 3 Cl H 79- 80 6 (b) and (b) — — — — 138-138 The agricultural compositions according to the inven¬ tion contain the active agents of the gαneral formula (I) i admixture with a solid or liquid carrier or diluent. The com positions may also comprise a surfactant and optionally oth additives commonly used in agricultural practice. The active agent content of the compositions may vary within O.Ol to 95 % by weight, preferably 0.1 to 90 % by weight. The solid carriers ' or diluents usable according to the invention may be e.g. natural or synthetic mineral substance such as silica, clay, talc, attapulgite, kaoline, calcium and aluminium silicates, calcium carbonate, dolomite, etc., furthermore solids of vegetable origin, e.g. sawdust, natur or synthetic resins, etc. Of the liquid carriers or diluents the following are t be mentioned: aliphatic, aromatic, aralipha ic or cyclic, hyd carbons, such as benzene, toluene, xylene, caclohexanol and cyclohexanone, water, alcohols, such as isopropanol and glyc mineral oil fractions, chlorinated hydrocarbons, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl keton etc. If the diluent is water, the composition according to the invention also comprises a surfactant. The surfactants applicable according to the invention may be ionic or non-ionic emulsifying, dispersing or wetting agents. Preferred surfactants are polycondensates of ethylene oxide with fatty acid derivatives, polycondensates of ethyl ene oxide with alkylphenols or arylphenols, alkali metal or alkaline earth metal lignosulfonates, alkyl-aryl sulfonic acids, salts of sulfosuccinic esters and sucrose derivatives With respect to the appropriate selection of the sur actants reference is made to US patent specification No. 3,713,804. The compositions according to the invention can be formulated as solid or liquid products. Of the solid compositions dusting powders, granulat microgranulates and powdery compositions are to be mention These solid compositions are utilized generally as such, wi out any further dilution. Compositions prepared as liquids or to be applied in the liquid state are e.g. wettable powders, e ulsifyable so tions and concentrates, suspendable ' powders and solutions. these compositions concentrates, emulsions and dispersions to be diluted with. ater are preferred. Dusting powders contain generally 0.1 to 5 % of acti ingredient in admixture with a carrier. Granulates and microgranulates contain generally 0.5 to 10 % by weight of active agent. These formulations are prepared by methods known per se, e.g. by impregnation tech niques. Granular compositions may also comprise other addit such as substances which control the release of active age Wettable powders contain generally 2.0 to 95 % by weight of active agent in admixture with a solid carrier an a surfactant, such as a wetting or dispersing agent. Wettable powders are prepared by thoroughly admixi or grinding together the active agent and the additives. Th resulting powder is easily wettable and suspendable and it can be diluted with water to any desired extent. The result aqueous compositions can be applied to the plants by spray E ulsifyable concentrates or solutions contain gener ally 1 to 50 w/v % of an active agent together with a solven such-as an aromatic hydrocarbon, and a surfactant, preferab an emulsifying agent. These compositions can be diluted with water to any desired extent before use. Suspendable powders comprise the active agent in a very finely dispersed state as an oily or aqueous suspension from which the solid particles do not settle. Such compositi comprise generally 5 to 80 % by weight of active agent. ' These concentrated suspensions are prepared by grind ing the active agent to a very fine powder and dispersing th resulting powder in a liquid carrier which also comprises th other additives. These suspensions can be diluted with water directly before use to any desired concentration, Some characteristic -compositions according to the invention are illustrated by the following Examples. Example I Wettable powder (a) Active agent No. 1 50 % by weight Sodium lignosulfonate 6 " Kaoline 44 " (b) Active agent No. 2 50 % by weight Sodiu ' lignosulfonate 5 " Isopropyl naphthalene sulfonate 1 " Talc 44 " (c) Active agent No. 1 90 % by weight Sodium dioctyl sulfosuccinate 0.2 " Synthetic silica 9.8 " (d) Active agent No. 4 80 % by weig Sodium alkyl naphthalene sulfonate 4 ** Methyl cellulose 2 " Kieselguhr 14 " Example II Emulsifyable concentrate (a) Active agent No. 1 250 g Condensate of ethylene oxide with alkyl phenol 30 S Calcium alkylaryl sulfonate 50 s Mineral oil fraction (bp.: 160-190°C) 670 s (b) Active agent No. 3 400 s Condensate of ethylene oxide with alkyl phenol 60 s Sodium alkylaryl sulfonate ' 40 s Cyclohexanone 150 g Xylene 400 s (c) Active agent No. 5 400 s Condensate of ethylene oxide with tri- styryϊ phenol phosphate 50 s Cyclohexanone 400 s Sodium alkyl benzene sulfonate 40 s Example III Suspendable concentrate Active agent No. 5 500 g Condensate of ethylene oxide with tristyryl phenol phosphate 50 g Condensate of ethylene oxide with alkyl phenol 50 g Polycarboxylic acid sodium salt 20 g Ethylene glycol 50 g Polysaccharide 1.5 g Water 320 g • Example IV Granulate Active agent No. 1 50 g Propylene glycol 25 g Vegetable oil 50 g Granular clay (diameter: 0.2-0.6 mm) 950 g The activity of the plant growth regulating αo pos tions according to the invention was tested under both green house and field conditions. A wettable powder of 5 % by weight active agent co tent was prepared by admixing the active agent in question with 40 % by weight of kaoline and 10 % by weight of a fatty alcohol sulfonate. The resulting wettable powder was diluted with water before use- to the desired concentration. . Lettuce and cucumber seeds were dressed by wetting them thoroughly with suspensions of -varying active agent content. The crossed seeds were- dried at room temperature for 48 hours and then germinated in Petri dishes on filter paper Ste and root lengths were measured on the 12th day for cucumber and on the 8th day for lettuce, and the data were compared to those of controls treated in the same way with distilled water. The results (stimulation or suppression) are summarized in Tables II and III. Plant growth regulating and damaging effects were also tested on beans under greenhouse conditions. Young bea plants grown in pots were treated in the two true leaves stage with 5ml of spray solution per plant, containing vary ing amounts of active agents. 3 weeks after treatment the effects exerted on internodium length and growth stage were assessed and compared to those observed on untreated controls. The results, expressed as percentages in relation to untreated controls, are listed in Tables IV and V. The phytotoxic effects were also evaluated. The data of Tables, II to V indicate that the composi¬ tions according to the invention exert growth retarding effect on the plants tested. The compositions significantly reduce stem and . root growth in relation to the untreated controls, and also significantly reduce inte nodial length. The ste and plant growth retarding effects of the compositions are at least identical to or even greater than those exerted by compositions comprising as active agent succinic acid-2,2-di- e hyl-cydrazide, a known plant growth regulating compound. The compositions according to the invention have no phytotoxic effects. The effects exerted on vegetative growth, flowering and crop yield were examined in three years* small parcel field tests on young (2-4 years old) apple trees. Apple tree varieties Gloster/M.9 and Starking Nm/N.9 of, strong or medium growth, respectively, were tested. The apple trees were sprayed until dripping with spray solutions containing varying amounts of active agents at the period of intense shooting. The trees were treated twice with a hand-operated spraying equipment. The lengths of two main shoots (predicted as having the strongest growth), each, were measured on every tree, the nodes were counted, and the individual shoots were marked prior to treatment. These shoots were measured twice again at a later phβnophasis of plant growth. At the end of the vegetative period, one skeletal branch was selected on each of the treated and control trees. The circumferences of the branches, and the lengths of the shoots shorter than 10 cm, to be regarded as potentially fructiferous parts, were ' 5 measured. The effects exerted on shoot growth and growth prope ties were evaluated in relation to untreated controls (Tables VI and- VII) . The data of Tablee VI indicate that phenoxyethyl succ 0 ate, in a higher dosage, considerably decreases the shoot growth on young trees. According to the data, the final . shoot length (70.1 cm) was only 81.4 % of that measured on treated trees. From the time of the first treatment to th end of vegetation period the total shoot growth measured on 5 treated trees was 3 .2 cm in average " , which, compared to th average value of 53 * 6 cm measured on " untreated plants, re¬ presents a decrease of 36.2 %. When applied . in a smaller dosage, phenoxyethyl succ ate has a shoot growth reducing effect of the same order as 0 succinic acid-2,2-dimethyl-hydrazide , a known very effecti plant growth reducing agent. It has been observed that on apple varieties of medium growth the number of fructiferous parts related to branch circumference increases significan upon treating the trees with the compositions according to 5 the invention (see Table VII). In the young apple plantation treated according to the invention the effects exerted on flowering and crop yi were examined in the year following the year of treatment. The results are shown in Table VIII. The data of Table VIII indicate that the composition according to the invention significantly promote bud forma¬ tion, and the extent of flowering (number of flowers/1 cm branch circumference) remarkably exceeds that observed on the untreated controls. Due to the stimulation of flowering, the compositio according to the invention also increase crop yield to a great extent. Related. to the untreated controls, an increas of 32 % in crop yield can be observed on Gloster apple and tha of 13-18 % on Starking variety, which represent a surplus of 2 tons/hectare in a 3 years plantation and a sur plus of 2.7 tons/hectare in a 5 years plantation. The efficiency of plant growth regulating activity can be increased when the active agent is applied in great amounts (0.4 % by volume) and in combination with 2-chloro- ethyl phos honic acid. The frost resistance of apple twigs was examined by their electrolytic conductivity measured after freezing in cryostate. It has been observed that the frost resistance o twigs obtained from trees treated according to the inventio is the same as, or sometimes even better than, that of the untreated ones. The new compositions according to the invention were also tested under small parcel field conditions on Pandy variety morello trees of low productivity. The trees were sprayed until dripping once in the flowering period. It was observed that the new compositions according to the inventi significantly increase fruit fixation. Compared to the results obtained after a treatment with an N-phenyl-phthala acid containing known composition, the crop yield increase by 50 % and the increase in crop yield vis about twofold i comparison with the untreated controls . Despite this extr great increase in crop yield, the average dimensions of th fruits do not decrease . Phenoxyethyl succinate exerts a favourable influenc on the growth characteristics of young apple trees, which be attributed to the reduction of shoot growth and the sti tion of flower bud formation. As a conseque nce , the crop y can be increased and the productive stage can be a ttained an earlier age . With morello trees of low productivity, the improve ment of fruit fixation and the extremely.high increase in crop yield are significantly advantageous results. The compositions according to the invention may al contain, beside the' compounds of the general- formula (I) , other, known plant regulating agents, furthermore plant pro ing agents, such as- herbicides, fungicides, bactericides and insecticides, as well as antidotes. The invention also relates to a process for regula ing plant growth, according to which plants are treated with an effective amount of a compound of the general formula (I) or with a composition containing such a compou Table II Concentra- Amount C u c u m b e r Active agent tion g/100 kg % by weight of seed Root length Ste length cm % increase re¬ % increase rela lated to the cm ed to the contr control Phenoxyethyl succinate 0.12 48 10.2 + 7.4 4.2 -19.3 0.06 24 8.6 - 9.5 3.9 -25.0 0.05 20 8.1 - 14.8 4.7 - 9.7 0.04 16 7.7 - 18.9 5.3 + 1.9 Control (treated with wa er) 9.5 5.2 Table III L e t t u c Active agent Concentra¬ tion, ppm Stem length, cm % increase related to the control Phenoxyethyl succinate 10 1.6 20 100 1.3 35 1000 1.1 45 j3-Naphthoxy-ethyl succinate 10 1.7 15 100 1.5 25 1000 1.3 35 ( -/4' -Chloro-2 ' -me thyl-phen- 10 1;6 20 " oxy/ -ethyl) succinate 100 0;8 60 1000 0.3 85 2-Methyl-2-(2 » ,4* ^'-brichloro- 10 1.7 15 phenoxy) -ethyl succinate 100 1.0 50 1000 0.2 90 Succinic acid-2,2-dimeth l- 10 1.5 25 hydrazide (known compound) 100 0.6 7P 1000 0.4 80 Control (treated with water) 2.0 Table IV Concentra¬ B e a s Active agent tion, Phytotoi % by wt . Plant Number of Internodi length city, % height, cm nodes % increase related to the control Phenoxyethyl 0,01 15.0 3 3.0 -26.8 0.0 succina e 0,05 14.5 2 2.3 -41.5 O.O 0.1 13.5 2 2,2 _46.4 0.0 0.5 12.6 1 • 2.1 -48.8 0.0 Control ( untreated) 18.5 4.1 Table V- Application B e a n s Phyto- ctive agent ra e toxic i b kg/ ectare Height, cm % increase related to the control % henoxyethyl succina e 0;06 7.0 16.7 0.0 0.6 5.5 34.6 olo -Naphthoxy-ethyl succinate O;06 8;0 4.8 0.0- 0.6 5.0 40.5 0.0 -(4-Chlorome th l-phenoxy) - 0;06 7.0 16;7 0;0 thyl succinate 0.6 6.0 28.6 0.0 -Methyl-2-(2 » ,4 » ,5'-tri- 0;06 4 ; 7 -44.1 0.0 lo o-phe oxy) -e thyl 0.6 3.4 -59.6 0.0 uccinate uccinic a cid-2, -di e th 1- 0;06 5.0 -40.5 0;0 ydrazide (known compound) 0.6 4.5 -46.6 0.0 ontrol (untreated) 8.4 Table VI Concentra¬ A p l e (G 1 o s t a v a r i e t y) Active agent tion, % by weight Growth 08.06-07. 3 Inter-* Growth 07, .23-10.05 Inter- Final le Shoot No. of nodium th Shoot No. of nodium of shoot length, nodes leng length 10.05 cm mm length, cm nodes mm Phenoxyethyl succinate 0.4 19.7 10.6 18.6 14.5 9.3 15.6 70.1 Control (un¬ treated) 28.3 14.0 20.2 25-3 13.4- 18.9 86.1 Measured at the end of the examination period Table VII Concentra¬ A p p l e (S t a r k i n g a r i e t y) ctive agent tion, % by weight Average shoot % increase relat- Productive part/ % increase length, cm ed to the control branch circum- related to th ference, cm control henoxyethyl succinate 0.2 23.4 •13.1 6.5 +38.2 * uccinic acid- 0.3 -2,2-dimethyl- and 23.4 ■ 13.1 3.8 -19.2 ydrazide (known 0.15 compound) Control (un¬ treated) 26.9 4.7 Table VIII Apple (var. Gloster) Apple (var. Sta king) Concentra¬ Active agent tion, % No. of flowers/ ' Crop yield No. of flowers/ Crop yi by weight branch circum- kg/ tree branch circum- kg/ ree ference, cm ference, cm Phenoxyethyl succinate 0.4 ' 3.6 8.6 - - Phenoxyethyl succinate O.2 - 8.2 23.1 Succinic acid- (2, - 0.3 + di ethyl-hyd a zide)+ 2-chloroethyl phosphon- 0.06 3.7 8.8 - ic acid Phenoxyethyl succinate 0,2 + + 2-chloroethyl phosphonic acid 0.06 _ 8.1 24.1 Control (untreated) - 3.0 6.6 5.9 20.4 Table IX Concentra« M o r e 1 1 o Active agent tion, % by weight No. of fruits/ Fruit diameter Fruit weight Crop yield 100 flowers mm g kg/ ree Phenoxyethyl succinate 0.04 27 23.4 6.12 38.4 N-phenyl-pht a 1- amic acid ( known 0.12 19 23.4 6.28 25.8 c ompound) Control ( un¬ treated) 20 23.5 6.37 21.2

Claims: AMENDED CLAIMS [received by the International Bureau on 14 October 1986 (14.10.86); original claims 1-9 replaced by amended claims 1-9 (3 pages)] 1. A mono- or di-(aryloxyeth l) succina te of the general formula ( I) , 0 Jl CH - C - 0 - A 1 ^ (I) CHg - <j| - 0 - A 0 wherein A represents hydrogen, a naphthoxye thyl group o.f formula (b) , or a substituted phenoxyethyl group of the general formula (a) and in this latter formula R stands for hydrogen or C, « alkyl, R is hydrogen, halo or C,_^ alkyl, and R 2 and Η each stand for hydrogen or halo, with the provisos that (i) at least one of R, R , R and R^ is other than hydrogen and (ii) at least one of the two A groups is other than hydrogen, or an agriculturally acceptable salt thereof. 2. A plant growth regulating composition characterized by containing as active agent at least one mono- or di-(aryl- oxyethyl) succinate of the general formula (I), wherein A is as defined in claim 1, or an agriculturally acceptable salt thereof. 3. A composition as claimed in cla im 2, characterized by containing 0.01 to 95 % by weight of active agent . 4. A composition as claimed in claim 2 or 3, character ized by containing a solid or liquid carrier or diluent and an ionic or non-ionic surfactant. 5. A composition as claimed in any of claims 2 to 4, characterized by also containing a known plant growth regula ting agent . 6. A process for the prepara tion of a mono- or di-(ary oxyethyl) succina te of the general formula (I) , wherein A is a s defined in claim 1 , or a salt of the monoesters , characterized in tha t succinic anhydride of the formula (II) is reacted with an aryloxy ethanol of the general formula ( HI) , wherein R is as defined in claim 1 and A* is the aromatic part of group (a) or (b) , and, if desired, a resulting mono- ester is converted into its salt. 7. A process as claimed in claim 6, characterized by utilizing the aryloxy ethanol in an amount of one molar equivalent. 8. A process as claimed in claim 6, characterized by utilizing the aryloxy ' ethanol in an amount of two molar equivalents. 9, A process for regulating plant growth, character¬ ized by applying onto the plant or seed an effective amount of a composition as claimed in any of claims 2 to 5*

Inventors: BELAI IVAN, BUBAN TAMAS, GERLEI OSZKARNE, KEREKES GYULA, KOVACS JANOSNE, MATOLCSY GYOERGY, VASARHELYI ENDRE, BELAI, IVAN, BUBAN, TAMAS, GERLEI, OSZKARNE, KEREKES, GYULA, KOVACS, JANOSNE, MATOLCSY, GYOERGY, VASARHELYI, ENDRE
Applicants: REANAL FINOMVEGYSZERGYAR
Application year: 1986
Main classification: C07C69
IPC codes: A01N39