GB1392111A - Carbamyloximino compounds and their use in pesticidal compositions - Google Patents

Carbamyloximino compounds and their use in pesticidal compositions

Info

Publication number
GB1392111A
GB1392111A GB1618772A GB1618772A GB1392111A GB 1392111 A GB1392111 A GB 1392111A GB 1618772 A GB1618772 A GB 1618772A GB 1618772 A GB1618772 A GB 1618772A GB 1392111 A GB1392111 A GB 1392111A
Authority
GB
United Kingdom
Prior art keywords
alkyl
compounds
prepared
alkenyl
proviso
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
GB1618772A
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.)
Diamond Shamrock Corp
Original Assignee
Diamond Shamrock Corp
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 Diamond Shamrock Corp filed Critical Diamond Shamrock Corp
Publication of GB1392111A publication Critical patent/GB1392111A/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
    • C07D295/04—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 substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—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 substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/125—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 substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—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 substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/18—Radicals substituted by singly bound hetero atoms other than halogen by sulfur atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

1392111 Carbamyloximino compounds DIAMOND SHAMROCK CORP 7 April 1972 [8 April 1971 24 Feb 1972] 16187/72 Heading C2C The invention comprises pesticidal compounds of the formula where: (a) R 2 and R 3 are the same or different and each represents a hydrogen atom or is as defined for R 1 ; (b) R 1 is an alkyl, alkenyl or alkynyl group or a substituted alkyl, alkenyl or alkynyl group, with the proviso that R 1 and R 2 may be connected to form a cycloaliphatic ring and with the proviso that R 1 , R 2 and R 3 together contain at least 2 carbon atoms; (c) R 4 and R 5 are the same or different and each represents a hydrogen atom or an alkyl, alkenyl or alkynyl group; (d) X is OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , 050 2 R 6 , NR 6 R 7 , NO 2 CN, SCN, N 3 or a halogen atom; (e) R 6 is a hydrogen atom or an alkyl, phenylalkyl, 2-thienyl-alkyl, alkenyl, alkynyl, aryl, substituted aryl, cyclohexyl, carbamyi, substituted carbamyl, acyl or substituted acyl group, with the proviso that the alkyl or alkenyl groups may be further substituted with X; and (f) R 7 is a hydrogen atom or an alkyl group, with the proviso that R 6 , R 7 and N in the NR 6 R 7 group may form a heterocyclic ring; and their production by reacting the corresponding oxime with R 4 NCO or with phosgene and then with R 4 R 5 NH; or by reacting a compound as above in which X is halogen with another compound HX in the presence of a hydrogen halide acceptor. Sulphinyl and sulphonyl compounds may be prepared by oxidation of thio compounds with sodium metaperiodate or acidic H 2 0 2 . Sulphonyloxy compounds are prepared from the HO-compound and sulphonyl chlorides. The compounds of the invention have insecticidal, miticidal and/or nematocidal activity. Ketoxime intermediates are prepared from the ketone and hydroxylamine in aqueous ethanol. 3,3 - Dimethyl - 1 - nitro - 2 - butanone oxime is prepared from NaNO 2 and the 1-bromo compound. Hydrocarbyloxy- and -thio-ketones are prepared by reacting α-haloketones with mercaptans or alcohols in the presence of an acid acceptor.
GB1618772A 1971-04-08 1972-04-07 Carbamyloximino compounds and their use in pesticidal compositions Expired GB1392111A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US13258471A 1971-04-08 1971-04-08
US229207A US3875232A (en) 1971-04-08 1972-02-24 AC Ketoxime carbamates

Publications (1)

Publication Number Publication Date
GB1392111A true GB1392111A (en) 1975-04-30

Family

ID=26830521

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1618772A Expired GB1392111A (en) 1971-04-08 1972-04-07 Carbamyloximino compounds and their use in pesticidal compositions

Country Status (20)

Country Link
US (1) US3875232A (en)
JP (1) JPS5533410B1 (en)
AR (1) AR192758A1 (en)
BE (1) BE830594Q (en)
CA (1) CA984399A (en)
CH (3) CH591433A5 (en)
DE (1) DE2216838C2 (en)
EG (1) EG10912A (en)
ES (1) ES401551A1 (en)
FR (1) FR2136055A5 (en)
GB (1) GB1392111A (en)
HU (1) HU165184B (en)
IE (1) IE36264B1 (en)
IL (1) IL39157A (en)
IT (1) IT954413B (en)
NL (1) NL175989C (en)
PL (1) PL89001B1 (en)
RO (3) RO61151A (en)
SU (3) SU466653A3 (en)
YU (3) YU39065B (en)

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4215075A (en) * 1971-04-08 1980-07-29 Diamond Shamrock Corporation Ketoxime carbamates
US3932471A (en) * 1972-02-24 1976-01-13 Diamond Shamrock Corporation Azide
DE2408522A1 (en) * 1974-02-22 1975-09-04 Boehringer Mannheim Gmbh AMINE DERIVATIVES OF AZIDOPHENOLS AND THE PROCESS FOR THEIR PRODUCTION
US4029688A (en) * 1974-06-27 1977-06-14 Union Carbide Corporation Carbamic pesticidal compositions
US4018894A (en) * 1975-01-20 1977-04-19 Stauffer Chemical Company Oxime carbonetes as fungicidal or bactericidal agents
US3988357A (en) * 1975-01-20 1976-10-26 Stauffer Chemical Company Certain oxime carbonates
US4009179A (en) * 1975-10-15 1977-02-22 E. I. Du Pont De Nemours And Company Di- and tri-substituted oxazolidin-2-one oximes
DE2621102A1 (en) 1976-05-10 1977-11-24 Schering Ag PROPANE-1,2-DIONE DIOXIME, SCHAEDLING KINKKKANKAGEN CONTAINING THESE COMPOUNDS AND THE PROCESS FOR THEIR PRODUCTION
US4073930A (en) * 1976-06-01 1978-02-14 Union Carbide Corporation Carbamoyloximes and oximes and insecticidal and miticidal compositions and methods employing them
US4072750A (en) * 1976-06-01 1978-02-07 Union Carbide Corporation 1,3,5-Trithiane and 1,3,5-oxadithiane carbamoyloxime compounds and insecticidal and miticidal compositions and methods employing them
US4454134A (en) * 1976-06-14 1984-06-12 Union Carbide Corporation Amide carbamates and amide oxime compounds
DE2631522A1 (en) * 1976-07-14 1978-01-19 Bayer Ag OXIME CARBAMATES OF FLUORINATED KETONES, METHOD FOR THEIR PRODUCTION AND USE AS INSECTICIDES, ACARICIDES AND NEMATICIDES
US4045491A (en) * 1976-10-07 1977-08-30 International Flavors & Fragrances Inc. α-Oxy(oxo) sulfides and ethers
DE2828133A1 (en) * 1978-06-27 1980-01-10 Bayer Ag N-SULFENYLATED CARBAMOYLOXIMINO-1-METHYLTHIO-BUTANES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS INSECTICIDES
CA1126278A (en) * 1978-11-09 1982-06-22 Paul Winternitz Carbamoyloximes
US4234514A (en) * 1978-12-04 1980-11-18 Diamond Shamrock Corporation Method of preparing ketoxime carbamates
US4264528A (en) * 1978-12-04 1981-04-28 Diamond Shamrock Corporation Method of preparing ketoxime carbamates
DE2933600A1 (en) * 1979-08-18 1981-04-09 Bayer Ag, 5090 Leverkusen SUBSTITUTED 2-CARBAMOYLOXIMINOBUTANE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS A PEST CONTROL
DE3125920A1 (en) 1981-07-01 1983-01-20 Basf Ag, 6700 Ludwigshafen "METHOD FOR PRODUCING SULFIDES"
US4387053A (en) * 1981-11-23 1983-06-07 Diamond Shamrock Corporation Stabilization of oxime carbamates with gallic acid, lower alkyl ester derivatives thereof
DE3204788A1 (en) * 1982-02-11 1983-08-18 Bayer Ag, 5090 Leverkusen METHOD FOR PRODUCING 5-SUBSTITUTED 1-CHLORINE-3,3-DIMETHYLPENTAN-2-ONES
US4640927A (en) * 1984-03-30 1987-02-03 Uniroyal Chemical Company, Inc. Substituted oxime carbamates
US4785108A (en) * 1984-06-04 1988-11-15 Uniroyal Chemical Company, Inc. Substituted oxime carbamates
US5200427A (en) * 1984-07-27 1993-04-06 The Board Of Trustees Of The Univ. Of Illinois Porphyric insecticides
GB2173499A (en) * 1985-02-04 1986-10-15 Ici Plc Fungicidal dithiolopyrrolones
US7842727B2 (en) * 2001-03-27 2010-11-30 Errant Gene Therapeutics, Llc Histone deacetylase inhibitors
CA2486303C (en) * 2002-05-22 2013-04-30 Errant Gene Therapeutics, Llc Histone deacetylase inhibitors based on alpha-ketoepoxide compounds
WO2003099789A1 (en) * 2002-05-22 2003-12-04 Errant Gene Therapeutics, Llc. Histone deacetylase inhibitors based on alphachalcogenmethylcarbonyl compounds

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA846786A (en) * 1970-07-14 R. Baker Don. Use of certain oxime esters in controlling fungi upon cellulosic materials
NL106827C (en) * 1957-01-21
NL298378A (en) * 1962-09-25
US3400153A (en) * 1964-09-23 1968-09-03 Union Carbide Corp Nitroalkyl carbamoyloximes
US3454642A (en) * 1966-12-22 1969-07-08 Upjohn Co Alkyl 2-methylpropenyl ketoxime carbamates
GB1214077A (en) * 1967-11-02 1970-12-02 Usv Pharma Corp Oximes and their carbamoyl esters and the methods of preparation thereof
NL6912150A (en) * 1968-08-19 1970-02-23
US3681386A (en) * 1969-11-06 1972-08-01 Minnesota Mining & Mfg Substituted alkanal oximes
CH536286A (en) * 1970-03-23 1973-04-30 Agripat Sa Process for the production of new carbamoyl oximes
US3647861A (en) * 1970-08-25 1972-03-07 Du Pont Substituted o-carbamylhydroxamates

Also Published As

Publication number Publication date
IE36264B1 (en) 1976-09-29
YU94472A (en) 1982-05-31
YU42298B (en) 1988-08-31
IT954413B (en) 1973-08-30
HU165184B (en) 1974-07-27
CA984399A (en) 1976-02-24
YU31579A (en) 1982-06-30
RO72827A (en) 1982-10-11
CH611275A5 (en) 1979-05-31
RO61151A (en) 1976-10-15
RO72853A (en) 1982-02-26
CH585194A5 (en) 1977-02-28
ES401551A1 (en) 1975-10-01
DE2216838C2 (en) 1985-05-09
IL39157A (en) 1976-08-31
SU466681A3 (en) 1975-04-05
DE2216838A1 (en) 1972-11-02
YU39102B (en) 1984-04-30
SU454735A3 (en) 1974-12-25
NL175989C (en) 1985-02-01
IE36264L (en) 1972-10-08
NL175989B (en) 1984-09-03
US3875232A (en) 1975-04-01
AR192758A1 (en) 1973-03-14
JPS5533410B1 (en) 1980-08-30
YU39065B (en) 1984-04-30
FR2136055A5 (en) 1972-12-22
CH591433A5 (en) 1977-09-15
BE830594Q (en) 1975-10-16
NL7204698A (en) 1972-10-10
PL89001B1 (en) 1976-10-30
IL39157A0 (en) 1972-06-28
SU466653A3 (en) 1975-04-05
YU31679A (en) 1982-05-31
EG10912A (en) 1976-12-31

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
732 Registration of transactions, instruments or events in the register (sect. 32/1977)
PE20 Patent expired after termination of 20 years