GB1392111A - Carbamyloximino compounds and their use in pesticidal compositions - Google Patents
Carbamyloximino compounds and their use in pesticidal compositionsInfo
- 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
Links
- 150000001875 compounds Chemical class 0.000 title abstract 6
- 230000000361 pesticidal effect Effects 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 title 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- -1 2-thienyl-alkyl Chemical group 0.000 abstract 4
- 125000000304 alkynyl group Chemical group 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 abstract 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- 235000008098 Oxalis acetosella Nutrition 0.000 abstract 1
- 240000007930 Oxalis acetosella Species 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 229910003460 diamond Inorganic materials 0.000 abstract 1
- 239000010432 diamond Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000012433 hydrogen halide Substances 0.000 abstract 1
- 229910000039 hydrogen halide Inorganic materials 0.000 abstract 1
- 230000000749 insecticidal effect Effects 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 230000003129 miticidal effect Effects 0.000 abstract 1
- ZFMWFLYWJJPZJK-UHFFFAOYSA-N n-(3,3-dimethyl-1-nitrobutan-2-ylidene)hydroxylamine Chemical compound CC(C)(C)C(=NO)C[N+]([O-])=O ZFMWFLYWJJPZJK-UHFFFAOYSA-N 0.000 abstract 1
- 230000001069 nematicidal effect Effects 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 150000002923 oximes Chemical class 0.000 abstract 1
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 abstract 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract 1
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 Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (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.
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) | CH611275A5 (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) | RO72827A (en) |
| SU (3) | SU466653A3 (en) |
| YU (3) | YU39065B (en) |
Families Citing this family (29)
| 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 |
| US3932508A (en) | 1974-04-26 | 1976-01-13 | Minnesota Mining And Manufacturing Company | Polyfluoromethylthio-substituted compounds |
| US4029688A (en) * | 1974-06-27 | 1977-06-14 | Union Carbide Corporation | Carbamic pesticidal compositions |
| US3988357A (en) * | 1975-01-20 | 1976-10-26 | Stauffer Chemical Company | Certain oxime carbonates |
| US4018894A (en) * | 1975-01-20 | 1977-04-19 | Stauffer Chemical Company | Oxime carbonetes as fungicidal or bactericidal agents |
| 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 |
| US4264528A (en) * | 1978-12-04 | 1981-04-28 | Diamond Shamrock Corporation | Method of preparing ketoxime carbamates |
| US4234514A (en) * | 1978-12-04 | 1980-11-18 | 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 |
| AU2003243272A1 (en) * | 2002-05-22 | 2003-12-12 | Errant Gene Therapeutics, Llc | Histone deacetylase inhibitors based on alpha-ketoepoxide compounds |
| AU2003247390A1 (en) * | 2002-05-22 | 2003-12-12 | Errant Gene Therapeutics, Llc. | Histone deacetylase inhibitors based on alphachalcogenmethylcarbonyl compounds |
Family Cites Families (10)
| 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 | |||
| BE637723A (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 |
-
1972
- 1972-02-24 US US229207A patent/US3875232A/en not_active Expired - Lifetime
- 1972-03-17 CA CA137,337A patent/CA984399A/en not_active Expired
- 1972-03-27 FR FR7210622A patent/FR2136055A5/fr not_active Expired
- 1972-04-05 AR AR241311A patent/AR192758A1/en active
- 1972-04-06 EG EG138/72A patent/EG10912A/en active
- 1972-04-07 IE IE453/72A patent/IE36264B1/en unknown
- 1972-04-07 RO RO7282519A patent/RO72827A/en unknown
- 1972-04-07 HU HUDI222A patent/HU165184B/hu unknown
- 1972-04-07 NL NLAANVRAGE7204698,A patent/NL175989C/en not_active IP Right Cessation
- 1972-04-07 PL PL1972154659A patent/PL89001B1/en unknown
- 1972-04-07 GB GB1618772A patent/GB1392111A/en not_active Expired
- 1972-04-07 RO RO7282518A patent/RO72853A/en unknown
- 1972-04-07 YU YU00944/72A patent/YU39065B/en unknown
- 1972-04-07 SU SU1886513A patent/SU466653A3/en active
- 1972-04-07 CH CH514972A patent/CH611275A5/xx not_active IP Right Cessation
- 1972-04-07 CH CH436875A patent/CH585194A5/xx not_active IP Right Cessation
- 1972-04-07 DE DE2216838A patent/DE2216838C2/en not_active Expired
- 1972-04-07 CH CH436975A patent/CH591433A5/xx not_active IP Right Cessation
- 1972-04-07 SU SU1887327A patent/SU466681A3/en active
- 1972-04-07 RO RO70445A patent/RO61151A/ro unknown
- 1972-04-07 IL IL39157A patent/IL39157A/en unknown
- 1972-04-07 SU SU1769624A patent/SU454735A3/en active
- 1972-04-07 IT IT49465/72A patent/IT954413B/en active
- 1972-04-07 ES ES401551A patent/ES401551A1/en not_active Expired
- 1972-04-07 JP JP3563572A patent/JPS5533410B1/ja active Pending
-
1975
- 1975-06-24 BE BE157643A patent/BE830594Q/en not_active IP Right Cessation
-
1979
- 1979-02-12 YU YU00315/79A patent/YU39102B/en unknown
- 1979-02-12 YU YU316/79A patent/YU42298B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| YU39065B (en) | 1984-04-30 |
| YU31579A (en) | 1982-06-30 |
| NL175989B (en) | 1984-09-03 |
| DE2216838C2 (en) | 1985-05-09 |
| HU165184B (en) | 1974-07-27 |
| YU39102B (en) | 1984-04-30 |
| JPS5533410B1 (en) | 1980-08-30 |
| CH591433A5 (en) | 1977-09-15 |
| FR2136055A5 (en) | 1972-12-22 |
| IL39157A0 (en) | 1972-06-28 |
| BE830594Q (en) | 1975-10-16 |
| DE2216838A1 (en) | 1972-11-02 |
| CH611275A5 (en) | 1979-05-31 |
| PL89001B1 (en) | 1976-10-30 |
| CH585194A5 (en) | 1977-02-28 |
| YU42298B (en) | 1988-08-31 |
| RO72827A (en) | 1982-10-11 |
| YU31679A (en) | 1982-05-31 |
| NL175989C (en) | 1985-02-01 |
| ES401551A1 (en) | 1975-10-01 |
| SU466653A3 (en) | 1975-04-05 |
| YU94472A (en) | 1982-05-31 |
| NL7204698A (en) | 1972-10-10 |
| EG10912A (en) | 1976-12-31 |
| SU466681A3 (en) | 1975-04-05 |
| IL39157A (en) | 1976-08-31 |
| US3875232A (en) | 1975-04-01 |
| SU454735A3 (en) | 1974-12-25 |
| IT954413B (en) | 1973-08-30 |
| RO72853A (en) | 1982-02-26 |
| RO61151A (en) | 1976-10-15 |
| AR192758A1 (en) | 1973-03-14 |
| IE36264L (en) | 1972-10-08 |
| IE36264B1 (en) | 1976-09-29 |
| CA984399A (en) | 1976-02-24 |
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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 |