EP0229098A1 - Pflanzenwachstumsregulierende verbindung und verfahren für die regelung des pflanzenwachstums - Google Patents

Pflanzenwachstumsregulierende verbindung und verfahren für die regelung des pflanzenwachstums

Info

Publication number
EP0229098A1
EP0229098A1 EP86903536A EP86903536A EP0229098A1 EP 0229098 A1 EP0229098 A1 EP 0229098A1 EP 86903536 A EP86903536 A EP 86903536A EP 86903536 A EP86903536 A EP 86903536A EP 0229098 A1 EP0229098 A1 EP 0229098A1
Authority
EP
European Patent Office
Prior art keywords
benzyl
ammonium chloride
tri
mass
regulating
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP86903536A
Other languages
English (en)
French (fr)
Inventor
József KARSAI
Endre Sebesty N
Sándor GAAL
Iván GARDI
Károly SIKI
György KISS
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Mem Novenyvedelmi Es Agrokemiai Kozpont
Original Assignee
Mem Novenyvedelmi Es Agrokemiai Kozpont
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Mem Novenyvedelmi Es Agrokemiai Kozpont filed Critical Mem Novenyvedelmi Es Agrokemiai Kozpont
Publication of EP0229098A1 publication Critical patent/EP0229098A1/de
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION 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
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02—Amines; Quaternary ammonium compounds
    • A01N33/12—Quaternary ammonium compounds

Definitions

  • the present invention relates to plant growth compositions containing benzyl trialkyl ammonium salta and a process for regulating the growth of planta.
  • R 1 , R 2 , R 3 are the same or different C 1 - C 1 6 alkyl ,
  • the compounds of the general formula I can be prepared by methods known per se , e. g. by the following reaction scheme:
  • the compounds of the general formula I can be prepared by reacting the appropriate benzyl halide (preferably chlorid or bromide) with the corresponding substituted trialkyl amine in the presence of a solvent at 20-150 °C or benzyl dialkyl amine and alkyl halide are reacted in a solvent or without any solvent according to the following reaction scheme:
  • Kantor and Hauser prepared benzyl tripropyl ammonium bromide by reacting benzyl bromide with tripropyl amine and benzyl tributyl ammonium bromide is prepared by reacting benzyl bromide with tributyl amine (J. Am. Chem. Soc. 73 /1951/ p. 4122).
  • Benzyl triallyl ammonium bromide was prepared by Butler and Bunch (J. Am. Chem. Soc. 71 /1949/ p. 3120) by heating of a mixture of diallyl benzyl amine and allyl bromide in acetophenone.
  • the anion of the benzyl trialkyl ammonium salts can be not only halogen ion.
  • Schlegel obtained benzyl trimethyl ammonium perchlorate by crystallizing a molequivalent benzyl trimethyl ammonium chloride and perchloric acid from an aqueous solution (Ber. Deutsch. Chem. Ges. 64 /1931/ p. 1739) and in this article the preparation of benzyl trimethyl ammonium benzene sulfonate is also described by reacting dimethyl benzyl amine with methyl benzene sulfonate in ether.
  • Plant growth regulating activity was disclosed for di-, trimethyl (cycloalkyl or alkenyl) ammonium salta in US-P
  • substituted benzyl trialkyl ammonium salts show, however, the disadvantage of the risky use. They can be applied to the plants by spray only during the very short ontogenesis period of the plants and the dose range within which the plants do not get injured, is very narrow.
  • J-To crop reduction or phytotoxic symptoms could be observed on the plants upon the spraying with the compositions according to the invention even in case of overdose or when it was not applied in the phenological atage suitable to get optimal effect.
  • Such tolerance was not observed in case of the substituted benzyl trialkyl ammonium salts, though such tolerance is the precondition of the safe use of a compound.
  • the compounds of the general formula I can be used as plant growth regulators per se or combined with other plant growth regulators applying same simultaneously or separately mainly in case of C 3 plants by spraying it in the vegetative or generative stage of development.
  • the amount of the compounds of the general formula I is influenced by the species, variety and development stage and condition of the plant and all factors acting upon the plant, all of which are known for someone skilled in the art or can be determined by someone skilled in the art.
  • the compounds of the general formula I can be preferably used in the vegetative and/or generative development of the plants by spraying them on the foliage at a rate of 50-5000 g/ha. preferably 100-1000 g/ha.
  • the compounds according to the invention can be used for seed dressing, preferably at a rate of 0.0005 g active ingredient related to 100 kg seeds.
  • a rate of 0.0005 g active ingredient related to 100 kg seeds When increasing the dosage of the compounds according .to the invention to 2.0 g/100 kg seeds, phytotoxic symptoms can be observed in case of some plants, these symptoms, however, disappear in a later stage of development.
  • the concentration of the compounds of the general formula I is in the range of 0.0001-90 % by mass, preferably 0.1-50 % by mass, preferably 10-20 % by mass.
  • compositions according to the invention can be prepared from the concentrated compositions by dilution.
  • compositions according to the invention are in the agriculture acceptable solid or liquid compositions, the preparation and use of which is possible due to the physical and chemical properties of the active ingredients.
  • compositions contain the active ingredients together with in the agriculture acceptable solid or liquid carriers and optionally surfactants.
  • the compositions may further contain additives which favourably effect the activity, such as reduce the decomposition of the active ingredients or make their use easier.
  • additives are e.g. protective colloids, thickening agent, substances promoting adhesion, adhesivea, stabilizers of adsorptive solid carriers.
  • a carrier any natural or artificial organic or inorganic substance can be used which is acceptable in the agriculture.
  • talc talc
  • gypaum sugar, salt, soda, chemical fertilizer, synthetic or natural silicates, silicic acid, dolomite, kaolin, vegetable or alga grist, starch etc.
  • Aa a liquid carrier water, alcohols, esters, ketones, mineral oil fraction, aromatic,aliphatic or cyclic hydrocarbons, halogenated hydrocarbons, halogenated hydrocarbons, dimethylsufoxide etc.
  • surfactans emulsifiers dispersing agents or wetting agents can be used and which can be ionogen or non-ionogen.
  • the surfactants the salts of lignin sulfonic acid, the salts of phenol sulfonic and naphtalin sulfonic acid, poly- condensates of ethylene oxide and fatty alcohols and fatty acids or fatty acid amides, aryl alkyl sulfonates, substituted phenols, such aa alkyl phenols, aryl phenols can be mentioned.
  • the solid compositions may be in the form of dusts, dusting agents or granulates.
  • the liquid compositions may be in the form of solutions, emulsifiable concentrates, emulsions, suspension concentrates, wettable powders, spray powders or pastes.
  • compositions according to the invention can te used together with other plant protecting agents, such as herbicides pesticides, fungicides, antibacterial agents, plant growth regulators and other compositions favourably influencing the amount and quality of the crop.
  • plant protecting agents such as herbicides pesticides, fungicides, antibacterial agents, plant growth regulators and other compositions favourably influencing the amount and quality of the crop.
  • any such plant protecting agent can be used together with the composition of the invention which is chemically compatible with the unsubstituted benzyl trialkyl ammonium salts and do not influence unfavourably the biological activity of each other.
  • plants are treated with a composition containing unsubstituted benzyl trialkyl ammonium salt alone or simultaneously or subsequently with other pesticides.
  • the amount of the active ingredients ia chosen so as to achieve the most effective desired regulating effect.
  • compositions are applied optionally in diluted form by conventional methods and equipments e.g. by spraying, dusting, vaporization, spreading.
  • the compounds in Table 1 were prepared by methods known per se. The typical preparation routes are shown by Examples. Chloride and bromide salts were prepared by reacting trialkyl amine with the corresponding benzyl halide. The melting point of the compounds correspond to reference data.
  • Benzyl tributyl ammonium chloride A mixture of 92.68 g. (0.5 mole) of tributyl amine and 63.29 g. (0.5 mole) benzyl chloride is boiled for 10 hours in 250 ml of acetonitrile. When the reaction ia completed (thin layer chromatography showed no benzyl chloride traces) the solvent is distilled off in vacuo in a rotatory film evaporator, the obtained white solid is washed with somewhat diethylether and dried in a vacuum drying oven. Thus 148 g. of white microcrystalline substance is obtained (yield: 94.9 %) m.p.: 154-155 °C
  • active ingredient of the general formula I e.g. tri-n-propyl benzyl ammonium chloride 5 % by mass of polyoxyethylene/2/ sorbitol-monolaurate /Tuieen 20/ 70 % by mass water 00 % by mass
  • active ingredient of the general formula I e.g. trimethyl benzyl ammonium chloride 5 % by mass of emulsifier e.g. /4-/1,1,3,3-tetramethyl- -butyl/-phenyl/-hydroxy-poly-/oxy/1,2-ethanediol/ /Triton X-100/ 7 % by mass dimethyl formamide 0 % by mass methylenechloride 0 % by mass
  • Example 7 Wettable powder 0 % by mass of active ingredient of the general formula I e.g. tri-n-butyl-benzyl ammonium chloride 3 % by mass of dispersing agent, e.g. magnesium lauryl sulphate
  • emulsifier e.g. sodium oleyl methyl tauride
  • active ingredient of the general formula I e.g. tri-n-butyl ammonium chloride 99.9 % by mass attapulgite type carrier 100 % by mass
  • the pots were placed to climatized chamber, and exposed to light for 16 hours, relative humidity: 75 %, daily temperature: 23 °C, hight temperature: 16 °C. 2 weeks after planting the plants were washed out of the soil.
  • the roots were then soaked in 1/4 diluted Hougland nutrient solution in order to remove the soil particles remaining on the root.
  • the test tubes were sealed with soft polyurethane foam in order to prevent evaporation and to support plants.
  • the test tubes were placed in to sand and kept in shadowed green-house for 48 hours. The plant height and the consumption of the nutrient solution were determined.
  • the compound increased the height in a concentration of 625-2500 mg/1 at a rate of 0.003125-0.125 mg active ingredient/pot, and the nutrient uptake was increased simultaneously by the increase of the height and mass.
  • composition was diluted so as to apply 2 1 solution related to 100 kg seeds.
  • 500 g seeds were dressed with proportionally reduced doses of dressing agent containing the active ingredient in the above given amount.
  • Germination of maize was stimulated at a dose of 200 mg-20 g/100 kg by 25-45 % upon using tri-n-butyl benzyl ammonium chloride. A total inhibition of germination was measured by increasing the date to 200 g/100 kg.
  • the evaluation was carried out on the 23rd day after treat- ment.
  • the spray liquid was 500 1/ha in each test.
  • the various tri-n-alkyl benzyl ammonium chloride salts under green-house conditions at the stage of 1 x 3 leaves did not reduce - with the exception of tri-n-butyl benzyl ammonium chloride - the soy-bean height, they rather increased same.
  • the height increase was usually accompanied with the increase of the shuck number and even the raw shuck mass was increased.
  • Out of the various tri-n- -alkyl benzyl ammonium chloride derivatives the activity of tri-n-butyl benzyl ammonium chloride was tested in free-land test under small parcel conditions in soy beans.
  • Test conditions Type of soil: green field "chernozem"
  • Green crop winter wheat .
  • Spray liquid amount 2201/ha Time of treatment: beginning of budding Treatments: 1./ untreated control 2./ tri-n-butyl benzyl ammonium chloride 125 g/ha 3./ tri-n-butyl benzyl ammonium chloride 250 g/ha
  • the soy-bean crop was increased by 7 to 17 % by applying tri- -n-butyl benzyl ammonium chloride at a rate of 125-500 g/ha by spraying. A more intensive increase (16-17 %) was observed in case of the lower rate (125-250 g/ha).
  • Time of treatment beginning of flowering Spray liquid was prepared from the composition containing 10 % by mass active ingredient formulated as disclosed in Example 12.
  • the table shows that when using tri-n-butyl benzyl ammonium chloride in peas by spraying it at the reate of 500 g/ha at the beginning of flowering the crop is increased by 15-21 %. By further increasing the sprayed liquid a crop reduction is caused.
  • T esting dimethyl tetradecyl benzyl ammonium chloride The test was carried out in green-house with nettle leated goosefoot (Chenopodim murale). Settle leated goosefoot of average height of 10 cm were planted to pots of a diameter of 12 cm filled with "chernozem” brown forest soil. When the seedlings took root their height was measured and the seedlings were, treated with the following doses of dimethyl tetradecyl benzyl ammonium chloride. 1./ untreated control
  • Spray liquid was prepared from the composition containing 10 % by mass of active ingredient formulated as given in Example 12. Table 9
  • I t shows that dimethyl tetradecyl benzyl ammonium chloride acts as plant growth regulator.
  • the daily growth rate of nettle leafed goosefoot was increased by 21-29 %, whereas by further increasing the dose the extent of growth intensity was by 10-36 % lower than that of the control.
  • Spray liquid was prepared from compositions formulated as given in Example 12 and containing 10 % by mass of active ingredient. Evaluation was carried out on the 40. day after the first treatment and on the 20. day after the 2. treatment.

Landscapes

  • 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)
EP86903536A 1985-06-05 1986-06-05 Pflanzenwachstumsregulierende verbindung und verfahren für die regelung des pflanzenwachstums Withdrawn EP0229098A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
HU852225A HU196887B (en) 1985-06-05 1985-06-05 Composition regulating the growth of plants containing as active substance derivatives of benzil-trialkylammonium
HU222585 1985-06-05

Publications (1)

Publication Number Publication Date
EP0229098A1 true EP0229098A1 (de) 1987-07-22

Family

ID=10958390

Family Applications (1)

Application Number Title Priority Date Filing Date
EP86903536A Withdrawn EP0229098A1 (de) 1985-06-05 1986-06-05 Pflanzenwachstumsregulierende verbindung und verfahren für die regelung des pflanzenwachstums

Country Status (6)

Country Link
EP (1) EP0229098A1 (de)
BR (1) BR8606711A (de)
DK (1) DK46187D0 (de)
FI (1) FI870441A7 (de)
HU (1) HU196887B (de)
WO (1) WO1986007237A1 (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104031243A (zh) * 2014-06-24 2014-09-10 上海大学 季铵盐类环氧树脂固化促进剂及其制备方法
CN106946717B (zh) * 2017-03-24 2019-02-19 广东洛斯特制药有限公司 苯扎氯铵单体合成工艺
CN106831446B (zh) * 2017-03-24 2019-02-19 广东洛斯特制药有限公司 一种改进的药用级苯扎氯铵单体生产方法
CN109232269A (zh) * 2018-10-31 2019-01-18 江西肯特化学有限公司 一种半干法工艺一步制备芐基三甲氯化铵的方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DD215228A1 (de) * 1983-05-11 1984-11-07 Bitterfeld Chemie Mittel zur beeinflussung des pflanzenwachstums und der pflanzenentwicklung i
DD215686A1 (de) * 1983-05-11 1984-11-21 Bitterfeld Chemie Mittel zur beeinflussung des pflanzenwachstums und der pflanzenentwicklung iii

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO8607237A1 *

Also Published As

Publication number Publication date
FI870441A0 (fi) 1987-02-02
FI870441A7 (fi) 1987-02-02
WO1986007237A1 (en) 1986-12-18
BR8606711A (pt) 1987-08-11
HU196887B (en) 1989-02-28
DK46187A (da) 1987-01-28
DK46187D0 (da) 1987-01-28
HUT41205A (en) 1987-04-28

Similar Documents

Publication Publication Date Title
NO130107B (de)
JPH01157905A (ja) 植物の生長調整法及び生長調整剤
US3829306A (en) Plant regulation with 2-halo-2',6'-disubstituted-n-amidomethyl-acetanilides
US4062962A (en) Substituted pyridines as systemic plant protectants
US3268323A (en) Method for regulating plant growth
WO1986007237A1 (en) Plant growth regulating compositions and process for regulating plant growth
US4227912A (en) Method for controlling the relative stem growth of plants
SU1486049A3 (ru) Способ регулирования роста сельскохозяйственных культур
US4620871A (en) Composition for increasing plant productivity protein nitrogen level and anion uptake, possessing kinetin-supplementing, cytokinin-like and membrane activities
US3989502A (en) Method for controlling growth of tobacco suckers
EP0044201B1 (de) 2-Chlor-4-trifluormethyl-thiazolcarbothiolsäuren und ihre Verwendung als Antidota
US3497343A (en) Method of stunting plant growth with substituted hydrazonium salts
JP2547739B2 (ja) イミダゾ−ル誘導体を有効成分とする植物生育調節剤
NO870463L (no) Plantevekstregulerende midler og fremgangsmaate for regulering av plantevekst.
CS214799B2 (cs) Prostředek k regulaci růstu rostlin a způsob výroby účinných látek
US4221582A (en) Plant growth regulating compounds, compositions and methods
EP0031690B1 (de) 0-alkyl-S-alpha-verzweigte Alkyl-alkylphosphondithioat-Insektizide und -Nematozide
CN1249746A (zh) 保护水稻不受乙草胺毒害的组合物
US4338118A (en) Plant growth regulation
CS231189B2 (en) Herbicide agent and processing method of active matter
JP7325429B2 (ja) 植物の耐塩性向上剤
CS208499B2 (en) Means for regulation of the plants growth,particularly the vegetables
US3687966A (en) O,o-di-(c1{14 c2 alkyl) s-{8 1-(c2{13 c20 acyl) hydantoin-3-yl{9 methyl phosphorthioates
US4718936A (en) 6-(3-thienylmethylamino)-purine, its preparation and its use
US4076517A (en) Method of inhibiting the growth of plants with phospholenium salts

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE CH DE FR GB IT LI LU NL SE

RIN1 Information on inventor provided before grant (corrected)

Inventor name: KARSAI, JOZSEF

Inventor name: SEBESTY N, ENDRE

Inventor name: SIKI, KAROLY

Inventor name: GAAL, SANDOR

Inventor name: GARDI, IVAN

Inventor name: KISS, GYOERGY

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 19880619

RIN1 Information on inventor provided before grant (corrected)

Inventor name: GAAL, SANDOR

Inventor name: SIKI, KAROLY

Inventor name: GARDI, IVAN

Inventor name: KISS, GYOERGY

Inventor name: KARSAI, JOZSEF

Inventor name: SEBESTY N, ENDRE