GB950348A - Plant growth regulants - Google Patents

Plant growth regulants

Info

Publication number
GB950348A
GB950348A GB42842/61A GB4284261A GB950348A GB 950348 A GB950348 A GB 950348A GB 42842/61 A GB42842/61 A GB 42842/61A GB 4284261 A GB4284261 A GB 4284261A GB 950348 A GB950348 A GB 950348A
Authority
GB
United Kingdom
Prior art keywords
acid
tetrahydrophthalamic
endomethylene
dimethylamino
prepared
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.)
Expired
Application number
GB42842/61A
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.)
Uniroyal Inc
Original Assignee
United States Rubber Co
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 United States Rubber Co filed Critical United States Rubber Co
Publication of GB950348A publication Critical patent/GB950348A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C07D295/28—Nitrogen atoms
    • C07D295/32—Nitrogen atoms acylated with carboxylic or carbonic acids, or their nitrogen or sulfur analogues
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/32—Cyclic imides of polybasic carboxylic acids or thio analogues thereof
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
    • C07C243/36—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/58—[b]- or [c]-condensed
    • C07D209/72—4,7-Endo-alkylene-iso-indoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/58—[b]- or [c]-condensed
    • C07D209/72—4,7-Endo-alkylene-iso-indoles
    • C07D209/76—4,7-Endo-alkylene-iso-indoles with oxygen atoms in positions 1 and 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Cultivation Of Plants (AREA)
  • Indole Compounds (AREA)

Abstract

A plant growth regulant composition comprises as active ingredient a compound selected from the group consisting of N-disubstituted-amino amic acids in which the disubstituted amino radical is any of dialkylamino radicals having 1 to 12 carbon atoms in each alkyl group, 1 - pyrrolidyl, 1 - piperidyl, or 4 - morpholinyl radicals, and the amic acid is any of hexahydrophthalamic acid, 1,2,3,6-tetrahydrophthalamic acid, 3,6 - endoxy - D 4 - tetrahydrophthalamic acid, and 3,6 - endomethylene - D 4 - tetrahydrophthalamic acid, and the salts and imids of the N-disubstitutedamino amic acids. Specified active ingredients are N-dimethylaminohexahydrophthalamic acid, N - dimethyl-amino - 1,2,3,6 - tetrahydrophthalamic acid, N - dimethylamino - 3,6 - endoxy - D 4 -tetrahydrophthalamic acid, N - dimethylamino3,6 - endomethylene - D 4 - tetrahydrophthalamic acid, N - dimethylamino - 3,6 - endomethylene - D 4 - tetrahydrophthalimide. The composition may be in the form of dusts with powdered solid carriers such as mica, talc, pyrophillite and clays or an aqueous solution or as solutions in organic solvents e.g. acetone, benzene or kerosene. Surface-active agents may be added to each of these forms of the composition. The invention comprises methods of regulating plant growth by applying the compounds to plants i.e. seeds, flowers, fruits, vegetables, roots and foliage or to soil in which seeds are planted. Examples given show the dwarfing effect on plants of the compounds. U.S.A. Specification 2,547,724 is referred to.ALSO:The invention comprises an N-disubstituted aminoamic acid in which the disubstituted amino radical is any of dialkylamino radicals having 1 to 12 carbon atoms in each alkyl group, 1-pyrrolidyl, 1-piperidyl, or 4-morpholinyl radicals, and the amic acid is any of hexahydrophthalamic acid, 1, 2, 3, 6-tetrahydrophthalamic acid, 3, 6-endoxy-D 4 -tetra-hydrophthalamic acid, and 3, 6-endomethylene-D 4 -tetrahydrophthalamic acid, and the salts and imides of the N-disubstituted amino amic acids. Per se compounds claimed are N-dimethylaminohexahydrophthalamic acid, N-dimethylamino-1, 2, 3, 6-tetrahydrophthalamic acid, N-dimethylamino-3, 6-endoxy-D 4 -tetrahydrophthalamic acid, N-dimethylamino-3, 6-endomethylene-D 4 -tetrahydrophthalamic acid, N-dimethylamino-3, 6-endomethylene-D 4-tetrahydrophthalimide. The N-disubstituted amino amic acids are prepared by reacting the selected 1, 1-disubstituted hydrazine with the anhydride of the selected dicarboxylic acid. The imides of these acids are prepared by removing water from the acid by means of acetic anhydride. The salts may readily be formed directly from the acid and a selected base such as an alkali-metal hydroxide or carbonate, or ammonia, or an amine. In an example N-dimethylamino-3, 6-endomethylene-D 4-tetrahydrophthalamic acid is prepared by reacting 1, 1-dimethylhydrazine with 3, 6-endomethylene-D 4-tetrahydrophthalamic anhydride. The N-dioctylamino, N-didodecylamino, N-(4-morpholinyl), N-(1-pyrrolidyl) and N-(1-piperidyl)-3, 6- endomethylene-D 4-tetrahydrophthalamic acids may similarly be prepared from 1, 1-dioctyl hydrazine, 1, 1-didodecyl-hydrazine, N-aminomorpholine, N-aminopyrrolidine, and N-aminopiperidine, respectively and 3, 6-endomethylene-D 4-tetrahydrophthalic anhydride. The other N-disubstituted amino amic acids may similarly be prepared from the anhydride of the selected hydrophthalic acid. In another example N-dimethylamino-3, 6-endomethylene-D 4-tetrahydrophthalimide is prepared by reacting N-dimethylamino-3, 6-endomethylene-D 4-tetrahydrophthalamic acid with acetic anhydride. Other examples show the production of N-dimethylaminohexahydrophthalamic acid, -1, 2, 3, 6-tetrahydrophthalamic acid, -3, 6, endoxy-D 4,tetrahydrophthalamic acid. U.S.A. Specification 2,547,724 is referred to.
GB42842/61A 1961-02-16 1961-11-30 Plant growth regulants Expired GB950348A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US8965561A 1961-02-16 1961-02-16

Publications (1)

Publication Number Publication Date
GB950348A true GB950348A (en) 1964-02-26

Family

ID=22218867

Family Applications (1)

Application Number Title Priority Date Filing Date
GB42842/61A Expired GB950348A (en) 1961-02-16 1961-11-30 Plant growth regulants

Country Status (5)

Country Link
BE (1) BE612380A (en)
DE (1) DE1468747B1 (en)
GB (1) GB950348A (en)
LU (1) LU41082A1 (en)
NL (9) NL6513672A (en)

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2576080A (en) * 1949-03-11 1951-11-20 Sharples Chemicals Inc Plant growth regulation
DE946857C (en) * 1951-06-13 1956-08-09 Pennsylvania Salt Mfg Company Preparations for influencing plant growth
GB760686A (en) * 1953-03-25 1956-11-07 Pennsylvania Salt Mfg Co Oxygen-bridged hydrogenated derivatives of phthalamic acid
US2637640A (en) * 1951-10-31 1953-05-05 Sharples Chemicals Inc Plant growth regulation
GB790646A (en) * 1955-05-09 1958-02-12 Whiffen And Sons Ltd Bismaleamic acid
DE1032021B (en) * 1956-07-12 1958-06-12 Dr Rer Nat Friedrich Schuette Method for combating pests on woody plants

Also Published As

Publication number Publication date
NL6603236A (en) 1966-06-27
LU41082A1 (en) 1962-03-12
NL6603064A (en) 1966-06-27
NL125076C (en)
BE612380A (en)
NL123754C (en)
DE1468747B1 (en) 1970-10-15
NL6513672A (en) 1965-12-27
NL6603063A (en) 1966-06-27
NL121528C (en)
NL125461C (en)
NL274654A (en)

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