GB1425763A - 2-nitromethylene- piperidines and their use as insecticides - Google Patents

2-nitromethylene- piperidines and their use as insecticides

Info

Publication number
GB1425763A
GB1425763A GB2081973A GB2081973A GB1425763A GB 1425763 A GB1425763 A GB 1425763A GB 2081973 A GB2081973 A GB 2081973A GB 2081973 A GB2081973 A GB 2081973A GB 1425763 A GB1425763 A GB 1425763A
Authority
GB
United Kingdom
Prior art keywords
alkyl
aryl
aralkyl
alkenyl
hydrogen
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
GB2081973A
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.)
Shell Internationale Research Maatschappij BV
Original Assignee
Shell Internationale Research Maatschappij BV
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 US00331155A external-priority patent/US3853888A/en
Application filed by Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV
Publication of GB1425763A publication Critical patent/GB1425763A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D211/74—Oxygen atoms
    • C07D211/76—Oxygen atoms attached in position 2 or 6

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Hydrogenated Pyridines (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

1425763 2 - (Nitromethylene) - piperidines SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ BV 2 May 1973 [4 May 1972 (2) 9 Feb 1973 (2)] 20819/73 Heading C2C [Also in Division A5] Novel compounds of Formula I: wherein n is 0, 1 or 2; X is alkyl, alkenyl, alkynyl, aryl, aralkyl, halogen, -CN, -C(O)-OH, -C(O)-O-alkyl, -C(O)-O- aryl, -C(O)-O-aralkyl, -O-C(O)-alkyl, -O-C(O)-aryl, -OH, -O-alkyl, -O- aryl, -O-alkoxyalkyl, -O-alkenyl, -O- aralkyl, -S-alkyl, -SO-alkyl, -SO 2 -alkyl, -NH 2 , -NH(alkyl), -N(alkyl) 2 , -C(O)NH 2 , -C(O)NH(alkyl), -C(O)N(alkyl) 2 , -NO 2 , = O (involving a ring carbon, -C(O)-H, -C(O)-alkyl, (mono- or polyhalo)alkyl, -SCN, -NHOH, -NH-O- (alkyl), hydrazino, or dialkylhydrazino; Y is hydrogen, alkyl, alkenyl, aryl, halogen, -CN, -C(O)NH 2 , -C(O)NH(alkyl), -C(O)N(alkyl) 2 , -NO 2 , -C(O)-H, -C(O)-alkyl or -C(O)- O-alkyl; and R is hydrogen, alkyl, alkenyl, aryl, aralkyl, alkynyl, (mono- or polyhalo)- alkyl, -C(O)-alkyl, -C(O)-aryl, -C(O)- O-alkyl, -C(O)NH 2 , -C(O)NH(alkyl), -C(O)N(alkyl) 2 , -O-alkyl, -NO 2 , -SCN, -halogen, alkoxyalkyl, cyanoalkyl, carboalkoxyalkyl, -(CH 2 ) m O-C(O)-alkyl, -CH 2 )- m C(O)-O-alkyl, -(CH 2 )- m C(O)NH 2 , -(CH 2 )- m C(O)NH(alkyl), or -(CH 2 )- m C(O)N(alkyl) 2 , m being 1 or 2; and if Y is hydrogen, R is hydrogen and n is 0, the equimolecular complex of an alkanesulphonic acid therewith, are prepared by reacting the corresponding valerolactam (2-piperidone) with a dialkyl sulphate or a trialkyloxonium fluoroborate, followed by base or an alkoxide to yield the corresponding 2-alkoxy-3,4,5,6-tetrahydropyridine or lactam acetal respectively, which is then reacted with nitromethane, a substituted nitromethane, or another 1-nitroalkane, the 2- (nitromethylene)-piperidine product being reacted further, if required, to introduce additional substituents. The examples describe the preparation of many piperidine derivatives of Formula I and their use as insecticides.
GB2081973A 1972-05-04 1973-05-02 2-nitromethylene- piperidines and their use as insecticides Expired GB1425763A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US25030572A 1972-05-04 1972-05-04
US25030672A 1972-05-04 1972-05-04
US33115873A 1973-02-09 1973-02-09
US00331155A US3853888A (en) 1972-05-04 1973-02-09 Piperidine insect control agents

Publications (1)

Publication Number Publication Date
GB1425763A true GB1425763A (en) 1976-02-18

Family

ID=27500350

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2081973A Expired GB1425763A (en) 1972-05-04 1973-05-02 2-nitromethylene- piperidines and their use as insecticides

Country Status (16)

Country Link
JP (1) JPS5626643B2 (en)
AU (1) AU472504B2 (en)
CA (1) CA978964A (en)
CH (1) CH583510A5 (en)
DD (1) DD105558A5 (en)
DE (1) DE2321523A1 (en)
EG (1) EG10835A (en)
FR (1) FR2196335B1 (en)
GB (1) GB1425763A (en)
HU (1) HU168688B (en)
IL (1) IL42170A (en)
IT (1) IT986985B (en)
NL (1) NL7306020A (en)
OA (1) OA04404A (en)
PL (1) PL89228B1 (en)
SU (1) SU888801A3 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002018339A2 (en) * 2000-08-30 2002-03-07 Dow Agrosciences Llc Compounds useful as insecticides, compounds useful as acaricides, and processes to use and make same

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6184234A (en) * 1984-10-03 1986-04-28 藤森工業株式会社 Manufacture of packaging bag
JPS61268257A (en) * 1985-05-24 1986-11-27 東洋製罐株式会社 Infusion container with window
CN1120839A (en) * 1993-04-08 1996-04-17 希巴-盖吉股份公司 Novel 2-nitromethylidene/2-cyanimino/2-nitro-imino-pyrrolidines and piperidines, intermediates, and their use as pesticides
DE60039299D1 (en) 1999-05-14 2008-08-07 Kaneka Corp METHOD FOR THE PRODUCTION OF OPTICALLY ACTIVE AZETIDIN-2-CARBOXYLIC ACIDS

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002018339A2 (en) * 2000-08-30 2002-03-07 Dow Agrosciences Llc Compounds useful as insecticides, compounds useful as acaricides, and processes to use and make same
WO2002018339A3 (en) * 2000-08-30 2002-05-16 Dow Agrosciences Llc Compounds useful as insecticides, compounds useful as acaricides, and processes to use and make same

Also Published As

Publication number Publication date
HU168688B (en) 1976-06-28
PL89228B1 (en) 1976-11-30
IL42170A (en) 1977-07-31
CA978964A (en) 1975-12-02
AU5514073A (en) 1974-11-07
AU472504B2 (en) 1976-05-27
IT986985B (en) 1975-01-30
JPS5626643B2 (en) 1981-06-19
FR2196335A1 (en) 1974-03-15
CH583510A5 (en) 1977-01-14
NL7306020A (en) 1973-11-06
FR2196335B1 (en) 1977-02-11
DD105558A5 (en) 1974-05-05
DE2321523A1 (en) 1973-11-15
DE2321523C2 (en) 1987-09-17
OA04404A (en) 1980-02-29
IL42170A0 (en) 1973-07-30
EG10835A (en) 1976-07-31
JPS4954532A (en) 1974-05-27
SU888801A3 (en) 1981-12-07

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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

Effective date: 19920502