IL39042A - 2,4,5-trioxoimidazolidine-1-carboxylic acid derivatives,their preparation and their use for the control of plant metabolism - Google Patents

2,4,5-trioxoimidazolidine-1-carboxylic acid derivatives,their preparation and their use for the control of plant metabolism

Info

Publication number
IL39042A
IL39042A IL39042A IL3904272A IL39042A IL 39042 A IL39042 A IL 39042A IL 39042 A IL39042 A IL 39042A IL 3904272 A IL3904272 A IL 3904272A IL 39042 A IL39042 A IL 39042A
Authority
IL
Israel
Prior art keywords
radical
trioxoimidazolidine
ethyl
methyl
acid
Prior art date
Application number
IL39042A
Other versions
IL39042A0 (en
Original Assignee
Ciba Geigy Ag
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
Priority claimed from CH451471A external-priority patent/CH552596A/en
Priority claimed from CH1168371A external-priority patent/CH570381A5/en
Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag
Publication of IL39042A0 publication Critical patent/IL39042A0/en
Publication of IL39042A publication Critical patent/IL39042A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/72—Two oxygen atoms, e.g. hydantoin
    • 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
    • A01N3/00—Preservation of plants or parts thereof, e.g. inhibiting evaporation, improvement of the appearance of leaves or protection against physical influences such as UV radiation using chemical compositions; Grafting wax
    • A01N3/02—Keeping cut flowers fresh chemically
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/96—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having three double bonds between ring members or between ring members and non-ring members

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • Toxicology (AREA)
  • Agronomy & Crop Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Claims (1)

1. CLAIMS 1. imidarolidlnetrione-carboxylic acid derivatives of formula I: (I) wherein represents hydrogen, an alkyl, lower alkenyl, lower alkynyl radical, a cycloalkyl radical, or a lower alkoxycarbonyl or lower alkylthio-carbonyl radical, a lower alkyl radical substituted by cycloalkyl, lower alkoxy, lower alkoxycarbonyl , lower alkylthio, lower dialkylamino or by halogen, a phenyl radical optionally substituted by halogen, nitro, lower alkyl , lower alkoxy or halogenalkyl , the tetrahydro-3- thienyl-S ,S-dioxide radical , a benzyl radical optionally ring-substituted by halogen or a tetrahydrofurfuryl radical, R2 represents an alkyl, lower alkenyl, lower alkynyl radical, a cycloalkyl radical , or a lower alkyl radical substituted by (lower alkoxy) (lower alkoxy) carbonyl , allyloxy , lower alkoxy or halogen, a phenyl radical optionally substituted by halogen or lower alkyl, a benzyl or phenylethyl radical optionally ring-substituted by halogen and/or nitro , or a furfuryl or tetrahydrofurfuryl radical, Y represents an oxygen or sulphur atom, and their addition salts with organic and inorganic acids. 39042/3 2. Imidazolidinetrionecarboxylic acid derivatives according to Claim 1 wherein and R2 independently represent an alkyl radical having up to 8 carbon atoms , a chloro- or bro oalkyl radical having up to 4 carbon atoms, an alkoxyalkyl radical having up to 5 carbon atoms, an alkenyl radical having up to 4 carbon atoms, a propargyl or butynyl radical, a cycloalkyl radical having up to 6 carbon atoms, which in the case of R^ can also be bound by way of -a. methyl , ethyl , n-propyl or n-butyl radical , a benzyl or phenylethyl (only R2) radical optionally mono- 20. III.72 to tri- ring-substituted by chlorine, bromine, iodine, nitro (only ^) or a phenyl radical optionally, mono- to tri- substituted by chlorine, bromine, iodine, methyl, ethyl and in the case of R^ also methoxy, ethoxy, nitro, trifluoromethyl , 20. III.72 and R^ can moreover also represent hydrogen, whilst Y stands for. oxygen or sulphur. 3. Imidazolidinetrionecarboxylic acid derivatives according to Claim 2 wherein Y represents oxygen, and wherein and R2 independently represent methyl, ethyl, n- propyl,. isopropyl, n-butyl, isobutyl, sec. butyl, tert. butyl, n-amyl, . isoamyl, n-hexyl, chloroethyl, chloropropyl, bromoethyl, bromopropyl , allyl, methallyl,. propargyl, cyclopropyl, cyclopropylmethyl (only R^) , a benzyl radical optionally monosubstituted by chlorine, or (in the case of 20. III.72 R2 onlY) nitro, or a phenyl radical optionally mono- or di- substituted by chlorine, bromine ,methyl, or in the case of R1 also 20. III.72 methoxy, and R, can moreover also represent hydrogen. 39042/2 ! 4. Imidazolidinetrionecarboxylic acid derivatives according to Claim 2 wherein Y represents sulphur, and 72 wherein R1 represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec.butyl, tert.butyl, n-amyl, isoamyl, n-hexyl, chloroethyl , chloropropyl , " ~" bromoethyl, brornopropyl , allyl, methallyl, propargyl, cyclopropyl, cyclopropylmethyl , benzyl, or a phenyl radical optionally mono- or di- substituted by chlorine, bromine, methoxy, methyl; and R2 rePresents methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec.butyl, tert.butyl, n-amyl, isoamyl, a benzyl radical optionally monosubstituted by chlorine, .72 methyl or nitro, or phenyl radical optionally mono- or di- substituted by chlorine, bromine, methyl, ethyl. 5. Imidazolidinetrionecarboxylic acid derivatives according to Claim 2 wherein Y represents oxygen, and one of the two substituents R1 and R2 represents an alkenyl radical and the other an alkyl radical, or both substituents represent an. alkyl radical, with the number of carbon atoms of and R^ together being between 3 and 6. 6. Imidazolidinetrionecarboxylic acid derivatives according to Claim 2 wherein Y represents sulphur, and one of the two substituents R-^ and represents an alkenyl radical, and the other an alkyl radical, or both substituents represent an alkyl radical, with the number of carbon atoms of and together being between 3 and 6. 7. 1-Methy1-2 ,4, 5-trioxoimidazolidine-3-carboxylic acid-ethyl ester according to Claim 1. 8. l-Methyl-2,4,5-trioxoimidazolidine-3-carboxylic acid-isopropyl ester according to Claim 1. 9. l-Methyl-2,4, 5-trioxoimidazolidine-3-carboxylic acid-n-butyl ester according to Claim 1. 10. l-Methyl-2,4,5-trioxoimidazolidine-3-carboxylic acid-isobutyl ester according to Claim 1. 11. l-Ethyl-2, 4, 5-trioxoimidazolidine-3-carboxylic acid-methyl ester according to Claim 1. 12. l-Ethyl-2, 4, 5-trioxoimidazolidine-3-carboxylic acid-ethyl ester according to Claim 1. 13. l-Ethyl-2 , 4, 5-trioxoimidazolidine-3-carboxylic acid-n-butyl ester according to Claim 1. 14. l-Ethyl-2, 4, 5-trioxoimidazolidine-3-carboxylic acid-isobutyl ester according to Claim 1. 15. l-Ethyl-2, 4, 5-trioxoimidazolidine-3-carboxylic acid-n-propyl ester according to Claim 1. 16. l-Methyl-2 , 4, 5-trioxoimidazolidine-3-carboxylic acid-sec.butyl ester according to Claim 1. 17·. l-Methyl-2 , 4, 5-trioxoimidazolidine-3-thiocarboxylic acid-S-ethyl ester according to Cla'im 1. 18. l-Methyl-2 , 4 , 5-trioxoimidazolidine-3-thiocarboxylic acid-S-n- propyl ester according to Claim 1. 19. l-Ethyl-2 , 4, 5-trioxoimidazolidine-3-thiocarboxylic acid-S-n- propyl ester according to Claim 1. 20. l-Methyl-2,4, 5- rioxoimidazolidine-3-thiocarboxylic acid-S-n-butyl ester according to Claim 1. 21. l-Ethyl-2 , 4, 5-trioxoimidazolidine-3-thiocarboxylic acid-S-n-butyl ester according to Claim 1. 22. l-Ethyl-2 , 4, 5-trioxoimidazolidine-3-thiocarboxylic acid-S-isopropyl ester according to Claim 1. 23. l-Methyl-2 , 4 , 5-trioxoimidazolidine-3-thiocarboxylic acid-S-isopropyl ester according to Claim 1. 24. l-Ethyl-2 , 4, 5-trioxoimidazolidine-3 -thiocarboxylic acid-S-ethyl ester according to Claim 1. 25. l-Methyl-2,4, 5-trioxoimidazolidine-3-thiocarboxylic acid-S-allyl ester according to Claim 1. 26 l-Ethyl-2,4, 5-trioxoimidazolidine-3-thiocarboxylic acid-S-allyl ester according to Claim 1. wherein has the meanings given under formula I; and the reaction of this, in the presence of an acid-binding agent, with a halogenoformic acid(thio) ester of formula IV: X - COYR2 (IV) wherein R2 and Y have the meanings given under formula I, and X represents halogen, especially chlorine or bromine; and, optionally, in \ the presence of an amino group, the formation of an additional salt with an inorganic or organic acid. 34. Process according to Claim 33, wherein there is used, as a functional derivative of oxalic acid: oxalyl halide, preferably oxalyl chloride or oxalyl bromide. 35. Process according to Claim 33, wherein there is used, as a functional derivative of oxalic acid: oxalyl halide semi-ester, preferably oxalyl chloride lower alkyl ester. 36. Process according to Claim 33, wherein there is used, as a functional derivative of oxalic acid: oxalic acid di-lower alkyl ester. 37. Process for the production of new imidazolidinetrione-3-carboxylic acid derivatives of formula I of Claim 1, the said process comprising the cyclisation of an allophanic acid ester of the formula: R1-NH-C0-NH-C00R2 , wherein R^ and R2 have the meaning given for formula I of of Claim 1, with an oxalyl halide, preferably with oxalyl chloride or oxalyl bromide; and, if represents hydrogen, optionally the further reaction of the obtained compound of the formul : 0 with a halide of the formula -halogen, wherein does not stand for hydrogen. 38. Agents for the control of plant metabolism, * the said agents containing as active substance at least one imidazolidinetrione-3-carboxylic acid derivative of Claim 1, in combination with carriers and/or distributing agents. 39. Agents according to Claim 37 containing a compound according to Claim 2. 40. Agents according to Claim 37 containing a compound according to Claim 3. 41. Agents according to Claim 37 containing a compound according to Claim 4. 42. Agents according to Claim 37 containing a compound according to Claim 5. i 43. Agents according to Claim 37 containing a compound according to any one of Claims 6 to 32. 44. Process for the control of fruit abscission, the said process comprising thie treatment of the plants, before their fruit is ripe for picking, with a compound according to Claim 1, either to the plants direct or to the soil. 45. Pnocess for the inhibition of senescence on plants, the said process comprising the treatment of the plants with a compound. according to Claim
1. C I B A - G E I G Y A.G. 2/Pk/nr
IL39042A 1971-03-26 1972-03-20 2,4,5-trioxoimidazolidine-1-carboxylic acid derivatives,their preparation and their use for the control of plant metabolism IL39042A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH451471A CH552596A (en) 1971-03-26 1971-03-26 1-substd-2,4,5-trioxoimidazolidine-3-carboxylic and thiocarboxylic - esters - used in growth control in plants
CH1168371A CH570381A5 (en) 1971-08-06 1971-08-06 1-substd-2,4,5-trioxoimidazolidine-3-carboxylic and thiocarboxylic - esters - used in growth control in plants

Publications (2)

Publication Number Publication Date
IL39042A0 IL39042A0 (en) 1972-05-30
IL39042A true IL39042A (en) 1976-04-30

Family

ID=25695670

Family Applications (1)

Application Number Title Priority Date Filing Date
IL39042A IL39042A (en) 1971-03-26 1972-03-20 2,4,5-trioxoimidazolidine-1-carboxylic acid derivatives,their preparation and their use for the control of plant metabolism

Country Status (12)

Country Link
JP (1) JPS565201B1 (en)
AR (1) AR193249A1 (en)
BE (1) BE781182A (en)
BG (1) BG20590A3 (en)
CA (1) CA987328A (en)
DD (1) DD102051A5 (en)
DE (1) DE2214448C3 (en)
FR (1) FR2131604A5 (en)
GB (1) GB1373556A (en)
IL (1) IL39042A (en)
IT (1) IT953546B (en)
NL (1) NL7204027A (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2306965B (en) * 1995-11-06 1999-09-01 American Cyanamid Co Aqueous spray compositions
US6197806B1 (en) 1995-12-20 2001-03-06 Nippon Zoki Pharmaceutical Co., Ltd. Eliminating agent for activated oxygen and free radicals
JPH10182460A (en) * 1996-12-27 1998-07-07 Nippon Zoki Pharmaceut Co Ltd 3-deoxyglucosone generation inhibitor
AU754989B2 (en) 1998-11-16 2002-11-28 Nippon Zoki Pharmaceutical Co., Ltd. A therapeutic agent for intractable vasculitis
JP4711523B2 (en) 2001-02-13 2011-06-29 日本臓器製薬株式会社 Hypoalbuminemia improving agent

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1670943B2 (en) * 1967-10-20 1976-12-02 Bayer Ag, 5090 Leverkusen PROCESS FOR PRODUCING PARABANIC ACID DERIVATIVES

Also Published As

Publication number Publication date
DE2214448B2 (en) 1981-05-21
CA987328A (en) 1976-04-13
DE2214448A1 (en) 1972-10-12
BG20590A3 (en) 1975-12-05
FR2131604A5 (en) 1972-11-10
DD102051A5 (en) 1973-12-05
JPS565201B1 (en) 1981-02-04
GB1373556A (en) 1974-11-13
IT953546B (en) 1973-08-10
DE2214448C3 (en) 1982-03-25
AR193249A1 (en) 1973-04-11
BE781182A (en) 1972-09-25
NL7204027A (en) 1972-09-28
IL39042A0 (en) 1972-05-30

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