CH627920A5 - Herbicide and process for its preparation - Google Patents
Herbicide and process for its preparation Download PDFInfo
- Publication number
- CH627920A5 CH627920A5 CH880877A CH880877A CH627920A5 CH 627920 A5 CH627920 A5 CH 627920A5 CH 880877 A CH880877 A CH 880877A CH 880877 A CH880877 A CH 880877A CH 627920 A5 CH627920 A5 CH 627920A5
- Authority
- CH
- Switzerland
- Prior art keywords
- octane
- trimethyl
- azabicyclo
- composition according
- active component
- Prior art date
Links
- 230000002363 herbicidal effect Effects 0.000 title claims description 25
- 238000002360 preparation method Methods 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 7
- 239000004009 herbicide Substances 0.000 title claims description 4
- -1 isopropyl 6-azabicyclo- (3.2.1) -octane-6-carboxylate Chemical compound 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 23
- 150000002148 esters Chemical class 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 12
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 239000002168 alkylating agent Substances 0.000 claims description 3
- 229940100198 alkylating agent Drugs 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000009472 formulation Methods 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- DYWSVUBJGFTOQC-UHFFFAOYSA-N xi-2-Ethylheptanoic acid Chemical compound CCCCCC(CC)C(O)=O DYWSVUBJGFTOQC-UHFFFAOYSA-N 0.000 claims description 3
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical group CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical class ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 2
- UDJUJZSBQFLNCM-UHFFFAOYSA-N S-ethyl 1,3,3-trimethyl-6-azabicyclo[3.2.1]octane-6-carbothioate Chemical compound C(C)SC(=O)N1C2CC(CC(C1)(C2)C)(C)C UDJUJZSBQFLNCM-UHFFFAOYSA-N 0.000 claims description 2
- ZDAVQPOSWCQTLX-UHFFFAOYSA-N ethyl 2-ethylheptanoate Chemical compound CCCCCC(CC)C(=O)OCC ZDAVQPOSWCQTLX-UHFFFAOYSA-N 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
- IOJSVCXNWBXHIU-UHFFFAOYSA-N 3,3,5-trimethyl-7-azabicyclo[3.2.1]octane-7-carbothioic s-acid Chemical compound C1C2CC(C)(C)CC1(C)CN2C(S)=O IOJSVCXNWBXHIU-UHFFFAOYSA-N 0.000 claims 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 2
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- QOLSPKHUUKOPGN-UHFFFAOYSA-N pentyl 1,3,3-trimethyl-6-azabicyclo[3.2.1]octane-6-carboxylate Chemical compound C(CCCC)OC(=O)N1C2CC(CC(C1)(C2)C)(C)C QOLSPKHUUKOPGN-UHFFFAOYSA-N 0.000 claims 1
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- ZTCBDXOJCDAYDP-UHFFFAOYSA-N s-methyl 3,3,5-trimethyl-7-azabicyclo[3.2.1]octane-7-carbothioate Chemical compound C1C2N(C(=O)SC)CC1(C)CC(C)(C)C2 ZTCBDXOJCDAYDP-UHFFFAOYSA-N 0.000 claims 1
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- 235000013312 flour Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 150000001469 hydantoins Chemical class 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 description 1
- BYVCTYDTPSKPRM-UHFFFAOYSA-N naphthalene-1-carbonyl naphthalene-1-carboxylate Chemical compound C1=CC=C2C(C(OC(=O)C=3C4=CC=CC=C4C=CC=3)=O)=CC=CC2=C1 BYVCTYDTPSKPRM-UHFFFAOYSA-N 0.000 description 1
- 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
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- QNMLMAVEXUCXRG-UHFFFAOYSA-N oxadiazinane-4,5-dione Chemical class O=C1CONNC1=O QNMLMAVEXUCXRG-UHFFFAOYSA-N 0.000 description 1
- SDRLFDJOSQLRPB-UHFFFAOYSA-N oxadiazine-4,5-dione Chemical class O=C1CON=NC1=O SDRLFDJOSQLRPB-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- YDCVQGAUCOROHB-UHFFFAOYSA-N oxadiazolidine-4,5-dione Chemical class O=C1NNOC1=O YDCVQGAUCOROHB-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- REJGOFYVRVIODZ-UHFFFAOYSA-N phosphanium;chloride Chemical class P.Cl REJGOFYVRVIODZ-UHFFFAOYSA-N 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- DJKSTIZKPGOSRU-UHFFFAOYSA-N propan-2-yl 1,3,3-trimethyl-6-azabicyclo[3.2.1]octane-6-carboxylate Chemical compound C(C)(C)OC(=O)N1C2CC(CC(C1)(C2)C)(C)C DJKSTIZKPGOSRU-UHFFFAOYSA-N 0.000 description 1
- YMEHFBNETWILFL-UHFFFAOYSA-N propan-2-yl 2-ethylheptanoate Chemical compound C(C)(C)OC(=O)C(CCCCC)CC YMEHFBNETWILFL-UHFFFAOYSA-N 0.000 description 1
- GIPIQOXJHPZYMD-UHFFFAOYSA-N propyl 2-ethylheptanoate Chemical compound CCCCCC(CC)C(=O)OCCC GIPIQOXJHPZYMD-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- BFZYLUGEHGYJKJ-UHFFFAOYSA-N pyrazolidine-3-thione Chemical class S=C1CCNN1 BFZYLUGEHGYJKJ-UHFFFAOYSA-N 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000005299 pyridinones Chemical class 0.000 description 1
- 150000008318 pyrimidones Chemical class 0.000 description 1
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical class OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 150000003246 quinazolines Chemical class 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- QCMHWZUFWLOOGI-UHFFFAOYSA-N s-ethyl chloromethanethioate Chemical compound CCSC(Cl)=O QCMHWZUFWLOOGI-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000003011 styrenyl group Chemical class [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- OLPRIZQBWZMBAS-UHFFFAOYSA-N thiadiazolidine 1,1-dioxide Chemical class O=S1(=O)CCNN1 OLPRIZQBWZMBAS-UHFFFAOYSA-N 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
- 150000003582 thiophosphoric acids Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762632915 DE2632915A1 (de) | 1976-07-19 | 1976-07-19 | 1,3,3-trimethyl-6-azabicyclo- (3.2.1)-octan-6-carbonsaeureester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH627920A5 true CH627920A5 (en) | 1982-02-15 |
Family
ID=5983626
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH880877A CH627920A5 (en) | 1976-07-19 | 1977-07-15 | Herbicide and process for its preparation |
Country Status (34)
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES303195A1 (es) * | 1963-08-19 | 1965-03-16 | Ciba Geigy | Procedimiento para la obtencion de acidos n-(n,n-bicicloalquilenoimino)-ditiocarbonicos. |
| US3820974A (en) * | 1970-08-05 | 1974-06-28 | Ciba Geigy Corp | Control of weeds with n carbenyl derivatives of azabicyclooctanes |
| US3705165A (en) * | 1970-08-05 | 1972-12-05 | Elmar Sturm | N-carbonyl derivatives of azabicyclooctanes |
-
1976
- 1976-07-19 DE DE19762632915 patent/DE2632915A1/de not_active Withdrawn
-
1977
- 1977-06-24 NL NL7707038A patent/NL7707038A/xx unknown
- 1977-07-01 YU YU01644/77A patent/YU164477A/xx unknown
- 1977-07-04 MX MX77100800U patent/MX4852E/es unknown
- 1977-07-04 CS CS774434A patent/CS192582B2/cs unknown
- 1977-07-05 FI FI772095A patent/FI772095A7/fi not_active Application Discontinuation
- 1977-07-05 IL IL52455A patent/IL52455A/xx unknown
- 1977-07-07 TR TR19833A patent/TR19833A/xx unknown
- 1977-07-11 CA CA282,400A patent/CA1100138A/en not_active Expired
- 1977-07-14 ES ES460737A patent/ES460737A1/es not_active Expired
- 1977-07-14 AU AU27008/77A patent/AU511783B2/en not_active Expired
- 1977-07-15 BG BG7736916A patent/BG27027A3/xx unknown
- 1977-07-15 CH CH880877A patent/CH627920A5/de not_active IP Right Cessation
- 1977-07-15 BG BG036916D patent/BG28027A3/xx unknown
- 1977-07-15 DD DD7700200094A patent/DD131070A5/xx unknown
- 1977-07-15 IE IE1472/77A patent/IE45359B1/en unknown
- 1977-07-15 LU LU77781A patent/LU77781A1/xx unknown
- 1977-07-16 PL PL1977199694A patent/PL103690B1/pl unknown
- 1977-07-18 DK DK324977A patent/DK324977A/da not_active Application Discontinuation
- 1977-07-18 GR GR53987A patent/GR71649B/el unknown
- 1977-07-18 FR FR7721934A patent/FR2359142A1/fr active Granted
- 1977-07-18 HU HU77SCHE615A patent/HU178752B/hu unknown
- 1977-07-18 NO NO772552A patent/NO147603C/no unknown
- 1977-07-18 PT PT66822A patent/PT66822B/pt unknown
- 1977-07-18 SE SE7708277A patent/SE424868B/xx unknown
- 1977-07-18 AT AT517477A patent/AT355861B/de not_active IP Right Cessation
- 1977-07-18 RO RO7791078A patent/RO71241A/ro unknown
- 1977-07-18 AR AR268467A patent/AR216084A1/es active
- 1977-07-18 BR BR7704733A patent/BR7704733A/pt unknown
- 1977-07-19 IT IT25888/77A patent/IT1113599B/it active
- 1977-07-19 GB GB30241/77A patent/GB1588934A/en not_active Expired
- 1977-07-19 ZA ZA00774346A patent/ZA774346B/xx unknown
- 1977-07-19 BE BE179455A patent/BE856933A/xx not_active IP Right Cessation
- 1977-07-19 SU SU772504515A patent/SU656464A3/ru active
- 1977-07-19 JP JP8657277A patent/JPS5312855A/ja active Granted
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| PL | Patent ceased |