GB1393993A - Agent for the regulation of plant growth - Google Patents

Agent for the regulation of plant growth

Info

Publication number
GB1393993A
GB1393993A GB2297372A GB2297372A GB1393993A GB 1393993 A GB1393993 A GB 1393993A GB 2297372 A GB2297372 A GB 2297372A GB 2297372 A GB2297372 A GB 2297372A GB 1393993 A GB1393993 A GB 1393993A
Authority
GB
United Kingdom
Prior art keywords
alkyl
hnr
novel
optionally substituted
stated
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
GB2297372A
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 AG
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
Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of GB1393993A publication Critical patent/GB1393993A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/38—One sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/48—Two nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/50—Three nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/60—Three or more oxygen or sulfur atoms

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)
  • Plural Heterocyclic Compounds (AREA)

Abstract

1393993 Pyrimidines CIBA-GEIGY AG 16 May 1972 [17 May 1971] 22973/72 Heading C2C Novel 5-nitropyrimidines of Formula I wherein R 1 represents C 2-6 alkyl, C 3-5 alkenyl, C 3-5 alkinyl, C 1-4 hydroxyalkyl, C 2-5 cyanoalkyl, or alkoxyalkyl or alkylamino alkyl or trialkylammonioalkyl wherein each alkyl moiety has 1-6 C atoms, or C 3-6 cycloalkyl optionally substituted by Me or Et; R 2 and R 3 which may be identical or different each represent H or C 1-6 alkyl; R 4 represents H, C 1-6 alkyl or C 3-6 cycloalkyl optionally substituted by Me or Et; R 5 represents C 1-6 alkyl; or R 1 and R 2 taken together form a C 2-6 polymethylene group, or R 3 and R 4 taken together form a C 4-6 polymethylene group, each of which may have a methylene group replaced by O or NR<SP>1</SP> where R<SP>1</SP> represents H or C 1-6 alkyl; and acid addition salts thereof with an inorganic or organic strong acid or quaternary salts thereof, may be prepared by exchanging the halogen atoms of a dihalopyrimidine of Formula IV successively with amines of formulµ HNR 1 R 2 and HNR 3 R 4 at a temperature between -60‹ C. and +120‹ C. in the presence of a base. Certain of the intermediate pyrimidines which may be isolated after the first step of the process, i.e. those containing a single halogen atom, are stated to be novel and these and the other novel compounds I of the invention exhibit plant growth regulant properties. An alternative preparative route for the compounds I is from the 2,4,6-trihalo-5-nitropyrimidine by reaction with HNR 1 R 2 and HNR 3 R 4 to give an intermediate (some of which are stated to be novel) which may be reacted with HSR 5 or an alkali metal salt thereof.
GB2297372A 1971-05-17 1972-05-16 Agent for the regulation of plant growth Expired GB1393993A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH722971A CH558137A (en) 1971-05-17 1971-05-17 MEANS OF INFLUENCING PLANT GROWTH.

Publications (1)

Publication Number Publication Date
GB1393993A true GB1393993A (en) 1975-05-14

Family

ID=4321885

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2297372A Expired GB1393993A (en) 1971-05-17 1972-05-16 Agent for the regulation of plant growth

Country Status (18)

Country Link
JP (1) JPS5654283B1 (en)
BG (1) BG19073A3 (en)
BR (1) BR7203098D0 (en)
CA (1) CA994773A (en)
CH (1) CH558137A (en)
CS (1) CS177082B2 (en)
DE (1) DE2223644A1 (en)
EG (1) EG10574A (en)
ES (1) ES402755A1 (en)
FR (1) FR2137933B1 (en)
GB (1) GB1393993A (en)
HU (1) HU164885B (en)
IL (1) IL39417A (en)
IT (1) IT955556B (en)
NL (1) NL7206602A (en)
SU (1) SU578825A3 (en)
TR (1) TR17050A (en)
ZA (1) ZA723325B (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991001310A1 (en) * 1989-07-21 1991-02-07 Beecham Group Plc Process for preparing 2,5-diamino-4,6-dichloropyrimidine
US7812159B2 (en) 2005-01-10 2010-10-12 Arena Pharamaceuticals, Inc. Processes for preparing aromatic ethers
US7838525B2 (en) 2003-07-11 2010-11-23 Arena Pharmaceuticals, Inc. Trisubstituted aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto
US8933083B2 (en) 2003-01-14 2015-01-13 Arena Pharmaceuticals, Inc. 1,2,3-trisubstituted aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto such as diabetes and hyperglycemia
US10894787B2 (en) 2010-09-22 2021-01-19 Arena Pharmaceuticals, Inc. Modulators of the GPR119 receptor and the treatment of disorders related thereto
US11007175B2 (en) 2015-01-06 2021-05-18 Arena Pharmaceuticals, Inc. Methods of treating conditions related to the S1P1 receptor
US11884626B2 (en) 2015-06-22 2024-01-30 Arena Pharmaceuticals, Inc. Crystalline L-arginine salt of (R)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclo-penta [b]indol-3-yl)acetic acid(Compound1) for use in S1P1 receptor-associated disorders

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH595061A5 (en) * 1974-05-10 1978-01-31 Ciba Geigy Ag
TWI229674B (en) * 1998-12-04 2005-03-21 Astra Pharma Prod Novel triazolo[4,5-d]pyrimidine compounds, pharmaceutical composition containing the same, their process for preparation and uses
MY148521A (en) 2005-01-10 2013-04-30 Arena Pharm Inc Substituted pyridinyl and pyrimidinyl derivatives as modulators of metabolism and the treatment of disorders related thereto
GB0512844D0 (en) * 2005-06-23 2005-08-03 Novartis Ag Organic compounds
KR20190116416A (en) 2017-02-16 2019-10-14 아레나 파마슈티칼스, 인크. Compounds and Methods for Treating Primary Bile Cholangitis

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991001310A1 (en) * 1989-07-21 1991-02-07 Beecham Group Plc Process for preparing 2,5-diamino-4,6-dichloropyrimidine
AU634564B2 (en) * 1989-07-21 1993-02-25 Beecham Group Plc Process for preparing 2,5-diamino-4,6-dichloropyrimidine
US8933083B2 (en) 2003-01-14 2015-01-13 Arena Pharmaceuticals, Inc. 1,2,3-trisubstituted aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto such as diabetes and hyperglycemia
US7838525B2 (en) 2003-07-11 2010-11-23 Arena Pharmaceuticals, Inc. Trisubstituted aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto
US8546429B2 (en) 2003-07-11 2013-10-01 Arena Pharmaceuticals, Inc. 1,2,3-trisubstituted aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto
US7812159B2 (en) 2005-01-10 2010-10-12 Arena Pharamaceuticals, Inc. Processes for preparing aromatic ethers
US10894787B2 (en) 2010-09-22 2021-01-19 Arena Pharmaceuticals, Inc. Modulators of the GPR119 receptor and the treatment of disorders related thereto
US11007175B2 (en) 2015-01-06 2021-05-18 Arena Pharmaceuticals, Inc. Methods of treating conditions related to the S1P1 receptor
US11884626B2 (en) 2015-06-22 2024-01-30 Arena Pharmaceuticals, Inc. Crystalline L-arginine salt of (R)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclo-penta [b]indol-3-yl)acetic acid(Compound1) for use in S1P1 receptor-associated disorders

Also Published As

Publication number Publication date
CA994773A (en) 1976-08-10
FR2137933B1 (en) 1973-07-13
HU164885B (en) 1974-05-28
BR7203098D0 (en) 1973-05-31
CH558137A (en) 1975-01-31
IT955556B (en) 1973-09-29
JPS5654283B1 (en) 1981-12-24
NL7206602A (en) 1972-11-21
IL39417A0 (en) 1972-07-26
TR17050A (en) 1974-04-25
DE2223644A1 (en) 1972-11-30
FR2137933A1 (en) 1972-12-29
ZA723325B (en) 1973-02-28
ES402755A1 (en) 1975-04-01
EG10574A (en) 1976-01-31
SU578825A3 (en) 1977-10-30
IL39417A (en) 1975-07-28
BG19073A3 (en) 1975-04-30
CS177082B2 (en) 1977-07-29

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee