US3867127A - Amine fruit abscission agents - Google Patents

Amine fruit abscission agents Download PDF

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Publication number
US3867127A
US3867127A US350273A US35027373A US3867127A US 3867127 A US3867127 A US 3867127A US 350273 A US350273 A US 350273A US 35027373 A US35027373 A US 35027373A US 3867127 A US3867127 A US 3867127A
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United States
Prior art keywords
acid
amine
parts
agents
active substances
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Expired - Lifetime
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US350273A
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English (en)
Inventor
Hanspeter Fischer
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.)
Novartis Corp
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Ciba Geigy Corp
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Publication date
Application filed by Ciba Geigy Corp filed Critical Ciba Geigy Corp
Priority to US05/529,427 priority Critical patent/US3986863A/en
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Publication of US3867127A publication Critical patent/US3867127A/en
Anticipated expiration legal-status Critical
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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
    • A01N33/04—Nitrogen directly attached to aliphatic or cycloaliphatic carbon atoms

Definitions

  • ABSTRACT Primary Examiner-Glennon H. Hollrah Attorney, Agent, or Firm-Harry lFalber [57] ABSTRACT
  • the present invention describes a composition and a method for the promotion of the abscission of fruits of all kinds particularly of citrus fruit.
  • the active princi ple therefore is an amine of formula I I wherein:
  • R is an alkyl or alkenyl radical of 8 to .22 carbon atoms
  • R and R are independently of each other hydrogen alkyl radicals of l to 12 carbon atoms. unsubstituted or substituted by amino, alkyl-or dialkylamino, as well as an acid addition or quaternary ammonium salt of such an amine.
  • the present invention relates to new agents for the promotion of the abscission of fruit of all kinds, particularly of citrus fruits, by the application, as active substances, of amines, their addition salts with inorganic or organic acids, as well as quaternary salts of such amines.
  • the active substances contained in the agents according to the invention are amines of formula 1 of 1 N Jx wherein R,, R and R have the meanings given under formula 1, R stands for a lower alkyl radical having 1 to 4 carbon atoms, and X for the anion of an inorganic or organic acid.
  • Alkyl radicals in these formulae are straight-chain or branched radicals.
  • the symbols R and R denote, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, as well as n-pentyl, n-
  • R represents, for example. noctyl, n-nonyl, n-decyl, n-undecyl, n-dodccyl, n tridecyl, n-tetradecyl. n-hexadecyl or n-octadecyl radicals, n-nonadecylamine, n-eicosylamine, and their branched isomers containing up to 22 carbon atoms.
  • Alkenyl radicals R can be straight-chain or branched: those preferred are the oleyl radical and the undecenyl radical.
  • Alkylaminoalkyl radicals and dialkylaminoalkyl radicals contain in all preferably 4 to 12 carbon atoms.
  • R represents the methyl, ethyl, npropyl or isopropyl radical or one ofthe butyl radicals.
  • Suitable addition salts are preferably salts of strong mineral acids such as hydrohalic acids: for example, hydrochloric acid, fluoboric acid (H81 nitric acid. phosphoric acid, thioor dithiophosphoric acids or sulphuric acid; or organic acids such as benzoic acid, halobenzoic acids, cinnamic acid and substituted cinnamic acids, naphthoic acid, acetic acid, haloacetic acids, propionic acid, halopropionic acids, butyric acid, lactic acid,-stearic acid, oxalic acid, tartaric acid, maleic acid,
  • hydrohalic acids for example, hydrochloric acid, fluoboric acid (H81 nitric acid. phosphoric acid, thioor dithiophosphoric acids or sulphuric acid; or organic acids such as benzoic acid, halobenzoic acids, cinnamic acid and substituted cinnamic acids,
  • the anion X of the quaternary salts can be an anion of the given acids.
  • amines and their salts (by which are meant in the following both the addition salts and the quaternary salts) contained in the agents according to the invention are known, and have been suggested for use as, among other things, herbicides'and defoliants.
  • the agents according to the invention can contain as active substances, for example, the following amines of 9r n u a I and rsalts Active substance Number Physical data:
  • addition salts of inorganic acids especially of hydrohalic acids.
  • outstanding among the quaternary salts are, in particular, the trimethylammonium salts of inorgarlic acids, e.g. of hydrohalic acids.
  • the active substances applicable are those which effect the promotion of fruit abscission but which do not produce defoliation.
  • hexadecylamine (palmitylamine, cetylamine).
  • the active substances are sprayed, as solutions in the given concentrations, onto branches well hung with fruit on various orange trees of the varieties Hamlin and Pineapple.
  • the results of the tests are evaluated after 7 days by the method developed by W. C. Wilson and C. H. Hendershott [Proc. Am. Soc. Hort. Sci. 90, 123-129 1967)].
  • the force to be applied to effect abscission of the fruit is measured; the results are expressed in the following table as percentages of the respective force measured in the case of the untreated s t t t- Force required to Active substance Concentration effect abscission, Defolinumber* in ppm as 7: of that measation ured in control test 7:
  • the active substances are used in the form of aqueous suspensions, emulsions and solutions, which are obtained from active-substance concentrates in the form of a. wettable powders and b. emulsion concentrates.
  • the agents according to the invention are produced in a manner known per se by the intimate mixing and- /or grinding of active substances of the general formula I with suitable carriers, optionally with the addition of dispersing agents or solvents which are inert to the active substances.
  • the active substances can be obtained and used in the following forms: water-dispersible active-substance concentrates:
  • Water-dispersible concentrates of active substances are agents which can be diluted with water to obtain any desired concentration. They consist of active substance, carrier, optionally additives which stabilise the active substance, surface-active substances, antifoam agents and, optionally, solvents.
  • concentration of active substance in these agents is between 5 and
  • the wettable powders and pastes are obtained by the mixing and grinding of the active substances with dispersing agents and pulverulent carriers, in suitable devices, until homogeneity is obtained.
  • Suitable carriers are, e.g.
  • kaolin talcum, bole, loess, chalk, limestone, ground limestone, attapulgite, dolomite, diatomaceous earth, precipitated silicic acid, alkaline-earth silicates, sodium and potassium aluminium silicates (feldspars and mica), calcium and magnesium sulphates, magnesium oxide, ground synthetic materials, fertilisers such as ammonium sulphate, ammonium phosphate, ammonium nitrate, urea, ground vegetable products such as bran, bark dust, sawdust, ground nutshells, cellulose powder, residues of plant extractions, active charcoal, etc., singly or in admixture with each other.
  • dispersing agents it is possible to use, e.g. condensation products of sulphonated naphthalene and sulphonated naphthalene derivatives with formaldehyde, condensation products of naphthalene or of naphthalene-sulphonic acids with phenol and formaldehyde, as well as alkali, ammonium and alkaline-earth metal salts of ligninsulphonic acid, also alkylarylsulphonates, al-
  • octadecanols and salts of sulphated fatty alcohol gylcol.
  • ethers the sodium salt of oleyl methyl tauride, ditertiary ethylene glycols, dialkyl dilauryl ammonium chloride, and fatty acid alkali-metal and alkaline-earth metal salts.
  • Suitable antifoam agents are, for example, silicones.
  • the active substances are so mixed, ground, sieved and strained with the above mentioned additives that the solid constituent in the case of wettable powders has a particle size not exceeding 0.02 to 0.04 mm.
  • dispersing agents are used such as those mentioned in the preceding paragraphs, organic solvents and water.
  • Suitable solvents are, e.g. alcohols, benzene, xylenes, toluene, dimethylsulphoxide, N,N-dialkylated amides, N-oxides of amines, particularly trialkylamines, and mineral oil fractions boiling in the range of to 350C.
  • the solvents must be practically odourless, non-phytotoxic, inert to the active substances and not readily combustible.
  • the agents according to the invention can be used in the form of solutions.
  • the active substance (or several active substances) of the general formula I is (or are) dissolved in water, or in suitable organic solvents, solvent mixtures, or mixtures of organic solvents with water.
  • organic solvents it is possible to use aliphatic and aromatic hydrocarbons, their chlorinated derivatives, alkylnaphthalenes, mineral oils on their own or in admixture with each other.
  • the solutions should contain the active substances in concentrations of from 1 to 20%.
  • agents according to the invention may also contain trace elements, and so forth.
  • Wettable Powders The following substances are used for the preparation of 25% wettable powders:
  • This concentrate can be mixed with water to form emulsions of suitable concentrations.
  • a method for the promotion of citrus fruit abscission which comprises applying to the citrus fruitbearing plants an effective amount of nonylamine.
  • a method for the promotion of citrus fruit abscission which comprises applying to the citrus fruitbearing plants an effective amount of decylamine.

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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)
US350273A 1972-04-19 1973-04-11 Amine fruit abscission agents Expired - Lifetime US3867127A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US05/529,427 US3986863A (en) 1973-04-11 1974-12-04 Amine fruit abscission agents

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH577472A CH564903A5 (enrdf_load_html_response) 1972-04-19 1972-04-19

Related Child Applications (1)

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US05/529,427 Continuation-In-Part US3986863A (en) 1973-04-11 1974-12-04 Amine fruit abscission agents

Publications (1)

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US3867127A true US3867127A (en) 1975-02-18

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US350273A Expired - Lifetime US3867127A (en) 1972-04-19 1973-04-11 Amine fruit abscission agents

Country Status (8)

Country Link
US (1) US3867127A (enrdf_load_html_response)
JP (1) JPS4919026A (enrdf_load_html_response)
CH (1) CH564903A5 (enrdf_load_html_response)
ES (1) ES413875A1 (enrdf_load_html_response)
GB (1) GB1403287A (enrdf_load_html_response)
IL (2) IL41987A (enrdf_load_html_response)
IT (1) IT982052B (enrdf_load_html_response)
ZA (1) ZA732668B (enrdf_load_html_response)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3986863A (en) * 1973-04-11 1976-10-19 Ciba-Geigy Corporation Amine fruit abscission agents
US4192671A (en) * 1977-09-14 1980-03-11 Basf Aktiengesellschaft Plant growth regulators
US4421547A (en) * 1982-04-06 1983-12-20 Stauffer Chemical Company 4-Hydroxy-5-isopropyl-2-methylphenyl trimethylammonium, 1-piperidine carboxylate salt of N-phosphonomethylglycine and its use as a herbicide

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS56126960A (en) * 1980-03-11 1981-10-05 Nec Corp Manufacture of semiconductor device

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3065066A (en) * 1958-10-03 1962-11-20 Rohm & Haas Method of defoliating plants employing aminos
US3460936A (en) * 1965-10-22 1969-08-12 Armour Ind Chem Co Long chain amine salts as plant growth regulators
US3506433A (en) * 1965-10-20 1970-04-14 Armour Ind Chem Co Plant growth control
US3660072A (en) * 1970-05-22 1972-05-02 Hawaiian Sugar Planters Assoc Ripening of sugarcane by use of certain quaternary ammonium halides

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3065066A (en) * 1958-10-03 1962-11-20 Rohm & Haas Method of defoliating plants employing aminos
US3506433A (en) * 1965-10-20 1970-04-14 Armour Ind Chem Co Plant growth control
US3460936A (en) * 1965-10-22 1969-08-12 Armour Ind Chem Co Long chain amine salts as plant growth regulators
US3660072A (en) * 1970-05-22 1972-05-02 Hawaiian Sugar Planters Assoc Ripening of sugarcane by use of certain quaternary ammonium halides

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3986863A (en) * 1973-04-11 1976-10-19 Ciba-Geigy Corporation Amine fruit abscission agents
US4192671A (en) * 1977-09-14 1980-03-11 Basf Aktiengesellschaft Plant growth regulators
US4421547A (en) * 1982-04-06 1983-12-20 Stauffer Chemical Company 4-Hydroxy-5-isopropyl-2-methylphenyl trimethylammonium, 1-piperidine carboxylate salt of N-phosphonomethylglycine and its use as a herbicide

Also Published As

Publication number Publication date
GB1403287A (en) 1975-08-28
CH564903A5 (enrdf_load_html_response) 1975-08-15
ES413875A1 (es) 1976-01-16
IL41999A0 (en) 1973-06-29
ZA732668B (en) 1974-02-27
IL41987A0 (en) 1973-06-29
IL41987A (en) 1976-03-31
JPS4919026A (enrdf_load_html_response) 1974-02-20
IT982052B (it) 1974-10-21

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