DE2621102A1 - Propan-1,2-diondioxime, schaedlingsbekaempfungsmittel enthaltend diese verbindungen sowie verfahren zu ihrer herstellung - Google Patents
Propan-1,2-diondioxime, schaedlingsbekaempfungsmittel enthaltend diese verbindungen sowie verfahren zu ihrer herstellungInfo
- Publication number
- DE2621102A1 DE2621102A1 DE19762621102 DE2621102A DE2621102A1 DE 2621102 A1 DE2621102 A1 DE 2621102A1 DE 19762621102 DE19762621102 DE 19762621102 DE 2621102 A DE2621102 A DE 2621102A DE 2621102 A1 DE2621102 A1 DE 2621102A1
- Authority
- DE
- Germany
- Prior art keywords
- berlin
- acid
- account
- bank
- methylthiopropane
- 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.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 title claims description 39
- 238000000034 method Methods 0.000 title claims description 34
- KFTHGQZJWAXFGG-UHFFFAOYSA-N N-(1-hydroxyiminopropan-2-ylidene)hydroxylamine Chemical compound ON=C(C)C=NO KFTHGQZJWAXFGG-UHFFFAOYSA-N 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 182
- XZNGJRLVGVUZPP-UHFFFAOYSA-N methyl N-hydroxy-2-hydroxyiminopropanimidothioate Chemical compound CSC(C(C)=NO)=NO XZNGJRLVGVUZPP-UHFFFAOYSA-N 0.000 claims description 79
- 150000005690 diesters Chemical class 0.000 claims description 73
- -1 methylcarbamoyl group Chemical group 0.000 claims description 35
- 239000002253 acid Substances 0.000 claims description 26
- 239000003960 organic solvent Substances 0.000 claims description 23
- YYLLOZJPNBMSIS-UHFFFAOYSA-N N-hydroxy-2-hydroxyiminopropanimidoyl chloride Chemical compound ON=C(C)C(Cl)=NO YYLLOZJPNBMSIS-UHFFFAOYSA-N 0.000 claims description 21
- 235000015244 frankfurter Nutrition 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 19
- 239000012948 isocyanate Substances 0.000 claims description 19
- 150000002513 isocyanates Chemical class 0.000 claims description 19
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 16
- UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical compound CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 claims description 15
- 239000004480 active ingredient Substances 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 9
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 8
- ZDGGJQMSELMHLK-UHFFFAOYSA-N m-Trifluoromethylhippuric acid Chemical compound OC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 ZDGGJQMSELMHLK-UHFFFAOYSA-N 0.000 claims description 8
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 5
- 239000000969 carrier Substances 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 239000000575 pesticide Substances 0.000 claims description 5
- ATCRIUVQKHMXSH-UHFFFAOYSA-N 2,4-dichlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1Cl ATCRIUVQKHMXSH-UHFFFAOYSA-N 0.000 claims description 4
- GAWCRULEMQFHTI-UHFFFAOYSA-N 4-chlorophenylisocyanic acid Natural products OC(=O)NC1=CC=C(Cl)C=C1 GAWCRULEMQFHTI-UHFFFAOYSA-N 0.000 claims description 4
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 claims description 4
- ILUJQPXNXACGAN-UHFFFAOYSA-N O-methylsalicylic acid Chemical compound COC1=CC=CC=C1C(O)=O ILUJQPXNXACGAN-UHFFFAOYSA-N 0.000 claims description 4
- 150000001266 acyl halides Chemical class 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 230000000749 insecticidal effect Effects 0.000 claims description 4
- GPSDUZXPYCFOSQ-UHFFFAOYSA-N m-toluic acid Chemical compound CC1=CC=CC(C(O)=O)=C1 GPSDUZXPYCFOSQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- KCMDLQKACKNGMB-UHFFFAOYSA-N n-hydroxy-2-oxopropanimidoyl chloride Chemical compound CC(=O)C(Cl)=NO KCMDLQKACKNGMB-UHFFFAOYSA-N 0.000 claims description 4
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 claims description 4
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 claims description 2
- AFPHTEQTJZKQAQ-UHFFFAOYSA-N 3-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1 AFPHTEQTJZKQAQ-UHFFFAOYSA-N 0.000 claims description 2
- OTLNPYWUJOZPPA-UHFFFAOYSA-N 4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-N 0.000 claims description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- QCIGLPLDNRDLQQ-UHFFFAOYSA-N butan-2-ylcarbamic acid Chemical compound CCC(C)NC(O)=O QCIGLPLDNRDLQQ-UHFFFAOYSA-N 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- SARZTZKPVBNGQE-UHFFFAOYSA-N propan-2-yl N-hydroxy-2-hydroxyiminopropanimidothioate Chemical compound C(C)(C)SC(C(C)=NO)=NO SARZTZKPVBNGQE-UHFFFAOYSA-N 0.000 claims description 2
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims description 2
- 150000005691 triesters Chemical class 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- MZAGXDHQGXUDDX-JSRXJHBZSA-N (e,2z)-4-ethyl-2-hydroxyimino-5-nitrohex-3-enamide Chemical compound [O-][N+](=O)C(C)C(/CC)=C/C(=N/O)/C(N)=O MZAGXDHQGXUDDX-JSRXJHBZSA-N 0.000 claims 1
- KNTZCGBYFGEMFR-UHFFFAOYSA-N (propan-2-ylazaniumyl)formate Chemical compound CC(C)NC(O)=O KNTZCGBYFGEMFR-UHFFFAOYSA-N 0.000 claims 1
- VPHHJAOJUJHJKD-UHFFFAOYSA-N 3,4-dichlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C(Cl)=C1 VPHHJAOJUJHJKD-UHFFFAOYSA-N 0.000 claims 1
- AWGBKZRMLNVLAF-UHFFFAOYSA-N 3,5-dibromo-n,2-dihydroxybenzamide Chemical compound ONC(=O)C1=CC(Br)=CC(Br)=C1O AWGBKZRMLNVLAF-UHFFFAOYSA-N 0.000 claims 1
- 150000008065 acid anhydrides Chemical class 0.000 claims 1
- 235000021167 banquet Nutrition 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 150000002430 hydrocarbons Chemical group 0.000 claims 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 12
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 12
- 238000001953 recrystallisation Methods 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 8
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
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- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
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- 239000002585 base Substances 0.000 description 4
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 4
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
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- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- XHRRYUDVWPPWIP-UHFFFAOYSA-N pentyl carbonochloridate Chemical compound CCCCCOC(Cl)=O XHRRYUDVWPPWIP-UHFFFAOYSA-N 0.000 description 1
- 239000004476 plant protection product Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000006308 propyl amino group Chemical group 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- NHCKWOHEDYQDHP-UHFFFAOYSA-N s-methyl 2-oxopropanethioate Chemical compound CSC(=O)C(C)=O NHCKWOHEDYQDHP-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
- HSFQBFMEWSTNOW-UHFFFAOYSA-N sodium;carbanide Chemical group [CH3-].[Na+] HSFQBFMEWSTNOW-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
Landscapes
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762621102 DE2621102A1 (de) | 1976-05-10 | 1976-05-10 | Propan-1,2-diondioxime, schaedlingsbekaempfungsmittel enthaltend diese verbindungen sowie verfahren zu ihrer herstellung |
| AU23493/77A AU507664B2 (en) | 1976-05-10 | 1977-03-22 | Propane-1, 2-dione-dioximes, a process for their manufacture and their use as pest-combating agents |
| TR19686A TR19686A (tr) | 1976-05-10 | 1977-03-29 | Propan-1,2-diyon,dioksim'ler bu bilesimleri ihtiva eden hasere ile muecadele muestahzarlari ve ayrica bunlarin ueretilmesine mahsus bir usul |
| DK137477A DK137477A (da) | 1976-05-10 | 1977-03-29 | Propan-1,2-diondioximer skadedyrsbekempelsesmidler indeholdende disse forbindelser samt en fremgangsmade til deres fremstilling |
| GB14125/77A GB1581382A (en) | 1976-05-10 | 1977-04-04 | Propane-1,2-dione-dioximes a process for their manufacture and their use as pest-combating agents |
| NL7703873A NL7703873A (nl) | 1976-05-10 | 1977-04-07 | Propaan-1,2-diondioximen, werkwijze voor het be- reiden daarvan, alsmede werkwijze voor het be- reiden van deze verbindingen bevattende midde- len ter bestrijding van schadelijke organismen. |
| CS772334A CS192576B2 (en) | 1976-05-10 | 1977-04-07 | Insecticide means and method of preparation of active substances |
| IE803/77A IE44486B1 (en) | 1976-05-10 | 1977-04-20 | Propane-1,2-dione-dioximes,a process for their manufacture and their use as pest-combating agents |
| SU772475653A SU650479A3 (ru) | 1976-05-10 | 1977-05-03 | Инсектицидное средство |
| IL52032A IL52032A (en) | 1976-05-10 | 1977-05-05 | Propane-1,2-dione-dioxime carbamates,a process for their manufacture and insecticidal compositions containing them |
| DD7700198802A DD129730A5 (de) | 1976-05-10 | 1977-05-06 | Schaedlingsbekaempfungsmittel |
| SU772477060A SU671723A3 (ru) | 1976-05-10 | 1977-05-06 | Способ получени пропан-1,2-диондиоксимов |
| IT23315/77A IT1075540B (it) | 1976-05-10 | 1977-05-09 | Propan-1,2-diondiossime,mezzi antiparassi tari contenenti tali composti e procedimento per la loro preparazione |
| LU77292A LU77292A1 (enExample) | 1976-05-10 | 1977-05-09 | |
| GR53416A GR70657B (enExample) | 1976-05-10 | 1977-05-09 | |
| AT329677A AT354805B (de) | 1976-05-10 | 1977-05-09 | Insektizides mittel |
| JP5363577A JPS52136120A (en) | 1976-05-10 | 1977-05-10 | New propanee1*22dioxydioxime and its method of manufacturing and insecticide containing said compound |
| BE177437A BE854456A (fr) | 1976-05-10 | 1977-05-10 | Propane-1,2-dionedioximes, leur procede de preparation et leur utilisation |
| FR7714199A FR2351099A1 (fr) | 1976-05-10 | 1977-05-10 | Propane-dione-dioximes et produits pesticides qui en contiennent |
| US06/150,172 US4358408A (en) | 1976-05-10 | 1980-05-15 | Propane-1,2-dionedioximes, pesticides containing these compounds, and the method for their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762621102 DE2621102A1 (de) | 1976-05-10 | 1976-05-10 | Propan-1,2-diondioxime, schaedlingsbekaempfungsmittel enthaltend diese verbindungen sowie verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2621102A1 true DE2621102A1 (de) | 1977-11-24 |
Family
ID=5977787
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762621102 Withdrawn DE2621102A1 (de) | 1976-05-10 | 1976-05-10 | Propan-1,2-diondioxime, schaedlingsbekaempfungsmittel enthaltend diese verbindungen sowie verfahren zu ihrer herstellung |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4358408A (enExample) |
| JP (1) | JPS52136120A (enExample) |
| AT (1) | AT354805B (enExample) |
| AU (1) | AU507664B2 (enExample) |
| BE (1) | BE854456A (enExample) |
| CS (1) | CS192576B2 (enExample) |
| DD (1) | DD129730A5 (enExample) |
| DE (1) | DE2621102A1 (enExample) |
| DK (1) | DK137477A (enExample) |
| FR (1) | FR2351099A1 (enExample) |
| GB (1) | GB1581382A (enExample) |
| GR (1) | GR70657B (enExample) |
| IE (1) | IE44486B1 (enExample) |
| IL (1) | IL52032A (enExample) |
| IT (1) | IT1075540B (enExample) |
| LU (1) | LU77292A1 (enExample) |
| NL (1) | NL7703873A (enExample) |
| SU (2) | SU650479A3 (enExample) |
| TR (1) | TR19686A (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0058346A3 (en) * | 1981-02-14 | 1983-01-26 | Bayer Ag | N sulfenyl oximecarbamates, preparation thereof and use thereof as pesticide |
| WO1990012784A1 (en) * | 1989-04-25 | 1990-11-01 | E.I. Du Pont De Nemours And Company | Fungicidal oxime carbamates |
| WO1991016299A1 (en) * | 1989-04-25 | 1991-10-31 | E.I. Du Pont De Nemours And Company | Fungicidal oxime carbamates |
| EP0738260B1 (en) * | 1994-01-05 | 2001-08-29 | Bayer Aktiengesellschaft | Pesticides |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3039269A1 (de) * | 1980-10-17 | 1982-05-19 | Bayer Ag, 5090 Leverkusen | Hydroxamsaeureester, verfahren zu ihrer herstellung, ihre verwendung in schaedlingsbekaempfungsmitteln und zwischenprodukte dafuer |
| TW438575B (en) * | 1996-08-28 | 2001-06-07 | Basf Ag | Compositions and methods for controlling harmful fungi |
| PH12012502415A1 (en) * | 2010-06-24 | 2015-07-08 | Ihara Chemical Ind Co | Alkoxyimino derivative and pest control agent |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3231599A (en) * | 1961-09-22 | 1966-01-25 | Union Carbide Corp | Bicyclic carbamyloximes |
| GB1138347A (en) | 1966-01-10 | 1969-01-01 | Du Pont | Carbamyl hydroxamate pesticides |
| NL130985C (enExample) * | 1967-02-09 | |||
| US3657307A (en) * | 1967-08-18 | 1972-04-18 | Du Pont | Dialkyl and dialkenyl n n'-bis(substituted carbamoyloxy) dithioloxalimidates |
| US3576834A (en) * | 1967-08-31 | 1971-04-27 | Du Pont | Substituted o-carbamylhydroxamates |
| DE2036491C3 (de) | 1970-07-23 | 1978-04-13 | Consortium Fuer Elektrochemische Industrie Gmbh, 8000 Muenchen | Schädlingsbekämpfungsmittel auf Ketoximcarbamat-Basis |
| US3875232A (en) | 1971-04-08 | 1975-04-01 | Diamond Shamrock Corp | AC Ketoxime carbamates |
| US3832375A (en) * | 1971-08-13 | 1974-08-27 | Fujisawa Pharmaceutical Co | Carbonic acid esters |
| US3901683A (en) * | 1973-07-23 | 1975-08-26 | Diamond Shamrock Corp | Crop yields with ketoximes |
| US4052194A (en) * | 1974-01-24 | 1977-10-04 | Merrill Wilcox | Oxime abscission agents |
| DE2409463A1 (de) | 1974-02-27 | 1975-09-04 | Bayer Ag | N-sulfenylierte oximcarbamate, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide, akarizide und nematizide |
| US4029688A (en) * | 1974-06-27 | 1977-06-14 | Union Carbide Corporation | Carbamic pesticidal compositions |
| US4096166A (en) * | 1975-02-04 | 1978-06-20 | E. I. Du Pont De Nemours And Company | Process for the preparation of carbamates of N-hydroxythioimidates |
| US4128581A (en) * | 1975-02-27 | 1978-12-05 | Diamond Shamrock Corporation | Ketoxime carbamates |
-
1976
- 1976-05-10 DE DE19762621102 patent/DE2621102A1/de not_active Withdrawn
-
1977
- 1977-03-22 AU AU23493/77A patent/AU507664B2/en not_active Expired
- 1977-03-29 DK DK137477A patent/DK137477A/da unknown
- 1977-03-29 TR TR19686A patent/TR19686A/xx unknown
- 1977-04-04 GB GB14125/77A patent/GB1581382A/en not_active Expired
- 1977-04-07 NL NL7703873A patent/NL7703873A/xx not_active Application Discontinuation
- 1977-04-07 CS CS772334A patent/CS192576B2/cs unknown
- 1977-04-20 IE IE803/77A patent/IE44486B1/en unknown
- 1977-05-03 SU SU772475653A patent/SU650479A3/ru active
- 1977-05-05 IL IL52032A patent/IL52032A/xx unknown
- 1977-05-06 SU SU772477060A patent/SU671723A3/ru active
- 1977-05-06 DD DD7700198802A patent/DD129730A5/xx unknown
- 1977-05-09 GR GR53416A patent/GR70657B/el unknown
- 1977-05-09 AT AT329677A patent/AT354805B/de not_active IP Right Cessation
- 1977-05-09 IT IT23315/77A patent/IT1075540B/it active
- 1977-05-09 LU LU77292A patent/LU77292A1/xx unknown
- 1977-05-10 FR FR7714199A patent/FR2351099A1/fr not_active Withdrawn
- 1977-05-10 BE BE177437A patent/BE854456A/xx unknown
- 1977-05-10 JP JP5363577A patent/JPS52136120A/ja active Pending
-
1980
- 1980-05-15 US US06/150,172 patent/US4358408A/en not_active Expired - Lifetime
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0058346A3 (en) * | 1981-02-14 | 1983-01-26 | Bayer Ag | N sulfenyl oximecarbamates, preparation thereof and use thereof as pesticide |
| US4470984A (en) * | 1981-02-14 | 1984-09-11 | Bayer Aktiengesellschaft | Combating pests with novel oxime-carbamates |
| WO1990012784A1 (en) * | 1989-04-25 | 1990-11-01 | E.I. Du Pont De Nemours And Company | Fungicidal oxime carbamates |
| EP0397345A1 (en) * | 1989-04-25 | 1990-11-14 | E.I. Du Pont De Nemours And Company | Fungicidal oxime carbamates |
| WO1991016299A1 (en) * | 1989-04-25 | 1991-10-31 | E.I. Du Pont De Nemours And Company | Fungicidal oxime carbamates |
| EP0738260B1 (en) * | 1994-01-05 | 2001-08-29 | Bayer Aktiengesellschaft | Pesticides |
Also Published As
| Publication number | Publication date |
|---|---|
| AT354805B (de) | 1979-01-25 |
| LU77292A1 (enExample) | 1977-08-24 |
| SU671723A3 (ru) | 1979-06-30 |
| AU2349377A (en) | 1978-09-28 |
| IL52032A (en) | 1980-12-31 |
| TR19686A (tr) | 1979-10-11 |
| NL7703873A (nl) | 1977-11-14 |
| CS192576B2 (en) | 1979-08-31 |
| IE44486B1 (en) | 1981-12-16 |
| US4358408A (en) | 1982-11-09 |
| IE44486L (en) | 1977-11-10 |
| IL52032A0 (en) | 1977-07-31 |
| ATA329677A (de) | 1979-06-15 |
| SU650479A3 (ru) | 1979-02-28 |
| FR2351099A1 (fr) | 1977-12-09 |
| IT1075540B (it) | 1985-04-22 |
| GB1581382A (en) | 1980-12-10 |
| DD129730A5 (de) | 1978-02-08 |
| GR70657B (enExample) | 1982-12-03 |
| JPS52136120A (en) | 1977-11-14 |
| AU507664B2 (en) | 1980-02-21 |
| BE854456A (fr) | 1977-11-10 |
| DK137477A (da) | 1977-11-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |