DE2210654A1 - 1 Anthrachinonyloxygruppe enthaltende Verbindungen und deren Verwendung als Herbizide - Google Patents
1 Anthrachinonyloxygruppe enthaltende Verbindungen und deren Verwendung als HerbizideInfo
- Publication number
- DE2210654A1 DE2210654A1 DE19722210654 DE2210654A DE2210654A1 DE 2210654 A1 DE2210654 A1 DE 2210654A1 DE 19722210654 DE19722210654 DE 19722210654 DE 2210654 A DE2210654 A DE 2210654A DE 2210654 A1 DE2210654 A1 DE 2210654A1
- Authority
- DE
- Germany
- Prior art keywords
- anthraquinonyl
- group
- compound
- anthraquinonyloxy
- weeds
- 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.)
- Pending
Links
- -1 anthraquinonyloxy group Chemical group 0.000 title claims description 77
- 150000001875 compounds Chemical class 0.000 title claims description 68
- 239000004009 herbicide Substances 0.000 title description 17
- 241000196324 Embryophyta Species 0.000 claims description 77
- BTLXPCBPYBNQNR-UHFFFAOYSA-N 1-hydroxyanthraquinone Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2O BTLXPCBPYBNQNR-UHFFFAOYSA-N 0.000 claims description 71
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 230000002363 herbicidal effect Effects 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 230000012010 growth Effects 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 150000002431 hydrogen Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- TXPCLHOSLKBTGP-UHFFFAOYSA-N 2-(9,10-dioxoanthracen-1-yl)oxyacetic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2OCC(=O)O TXPCLHOSLKBTGP-UHFFFAOYSA-N 0.000 claims description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 5
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- AFQKMRAPRMSXAT-UHFFFAOYSA-N 2-chloroethyl (9,10-dioxoanthracen-1-yl) carbonate Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2OC(=O)OCCCl AFQKMRAPRMSXAT-UHFFFAOYSA-N 0.000 claims description 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
- BUXRYIQWNPZNOP-UHFFFAOYSA-N (9,10-dioxoanthracen-1-yl) ethyl carbonate Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2OC(=O)OCC BUXRYIQWNPZNOP-UHFFFAOYSA-N 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 3
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- 239000003513 alkali Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 238000009305 arable farming Methods 0.000 description 1
- 230000027455 binding Effects 0.000 description 1
- 238000009739 binding Methods 0.000 description 1
- 230000028446 budding cell bud growth Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-M carbonochloridate Chemical compound [O-]C(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-M 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 231100000762 chronic effect Toxicity 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000036449 good health Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 235000021331 green beans Nutrition 0.000 description 1
- 239000003966 growth inhibitor Substances 0.000 description 1
- 231100000001 growth retardation Toxicity 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- DPOMQPDYGCPLES-UHFFFAOYSA-N methyl 4-(9,10-dioxoanthracen-1-yl)oxybenzenesulfonate Chemical compound C1=CC(S(=O)(=O)OC)=CC=C1OC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O DPOMQPDYGCPLES-UHFFFAOYSA-N 0.000 description 1
- OFCCYDUUBNUJIB-UHFFFAOYSA-N n,n-diethylcarbamoyl chloride Chemical compound CCN(CC)C(Cl)=O OFCCYDUUBNUJIB-UHFFFAOYSA-N 0.000 description 1
- DWLVWMUCHSLGSU-UHFFFAOYSA-M n,n-dimethylcarbamate Chemical compound CN(C)C([O-])=O DWLVWMUCHSLGSU-UHFFFAOYSA-M 0.000 description 1
- XNBKKRFABABBPM-UHFFFAOYSA-N n,n-diphenylcarbamoyl chloride Chemical compound C=1C=CC=CC=1N(C(=O)Cl)C1=CC=CC=C1 XNBKKRFABABBPM-UHFFFAOYSA-N 0.000 description 1
- PJLHXSBKGRJXHA-UHFFFAOYSA-N n-ethylcarbamoyl chloride Chemical compound CCNC(Cl)=O PJLHXSBKGRJXHA-UHFFFAOYSA-N 0.000 description 1
- CPGWSLFYXMRNDV-UHFFFAOYSA-N n-methyl-n-phenylcarbamoyl chloride Chemical compound ClC(=O)N(C)C1=CC=CC=C1 CPGWSLFYXMRNDV-UHFFFAOYSA-N 0.000 description 1
- GSTILDPJAZBDGO-UHFFFAOYSA-N n-piperidin-1-ylcarbamoyl chloride Chemical compound ClC(=O)NN1CCCCC1 GSTILDPJAZBDGO-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 125000006611 nonyloxy group Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 230000019612 pigmentation Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000003375 plant hormone Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- IVRIRQXJSNCSPQ-UHFFFAOYSA-N propan-2-yl carbonochloridate Chemical compound CC(C)OC(Cl)=O IVRIRQXJSNCSPQ-UHFFFAOYSA-N 0.000 description 1
- FBNCDBZHLBYPGY-UHFFFAOYSA-N pyridine;dihydrochloride Chemical compound [Cl-].[Cl-].C1=CC=[NH+]C=C1.C1=CC=[NH+]C=C1 FBNCDBZHLBYPGY-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Chemical class 0.000 description 1
- COEZWFYORILMOM-UHFFFAOYSA-M sodium 4-[(2,4-dihydroxyphenyl)diazenyl]benzenesulfonate Chemical compound [Na+].OC1=CC(O)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 COEZWFYORILMOM-UHFFFAOYSA-M 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C66/00—Quinone carboxylic acids
- C07C66/02—Anthraquinone carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12152071A | 1971-03-05 | 1971-03-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2210654A1 true DE2210654A1 (de) | 1972-09-21 |
Family
ID=22397219
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722210654 Pending DE2210654A1 (de) | 1971-03-05 | 1972-03-06 | 1 Anthrachinonyloxygruppe enthaltende Verbindungen und deren Verwendung als Herbizide |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5231011B1 (enExample) |
| BE (1) | BE780206A (enExample) |
| CA (1) | CA974520A (enExample) |
| CH (1) | CH566718A5 (enExample) |
| DE (1) | DE2210654A1 (enExample) |
| FR (1) | FR2128591B1 (enExample) |
| GB (1) | GB1382721A (enExample) |
| IL (1) | IL38840A0 (enExample) |
| IT (1) | IT953441B (enExample) |
| NL (1) | NL7202877A (enExample) |
| ZA (1) | ZA721148B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0134198A1 (de) * | 1983-08-10 | 1985-03-13 | Ciba-Geigy Ag | Verwendung von Chinonderivaten zum Schützen von Kulturpflanzen vor der phytotoxischen Wirkung von Herbiziden |
| WO1994017070A1 (de) * | 1993-01-20 | 1994-08-04 | Basf Aktiengesellschaft | Derivate des azaanthrachinons und des azaxanthons und diese enthaltende herbizide und pflanzenwachstumsregulatoren |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6432766B2 (ja) * | 2014-09-17 | 2018-12-05 | 川崎化成工業株式会社 | 光ラジカル重合開始剤 |
| MX2024000507A (es) | 2021-07-08 | 2024-01-31 | Agrematch Ltd | Composiciones para la proteccion de cultivos. |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1263352A (en) * | 1969-06-25 | 1972-02-09 | Ici Ltd | Quinone carbamates and their use as pesticides |
-
1972
- 1972-02-18 CA CA135,081A patent/CA974520A/en not_active Expired
- 1972-02-21 GB GB790872A patent/GB1382721A/en not_active Expired
- 1972-02-21 ZA ZA721148A patent/ZA721148B/xx unknown
- 1972-02-25 IL IL38840A patent/IL38840A0/xx unknown
- 1972-03-02 CH CH304172A patent/CH566718A5/xx not_active IP Right Cessation
- 1972-03-03 NL NL7202877A patent/NL7202877A/xx unknown
- 1972-03-03 FR FR7207487A patent/FR2128591B1/fr not_active Expired
- 1972-03-03 JP JP47022685A patent/JPS5231011B1/ja active Pending
- 1972-03-03 BE BE780206A patent/BE780206A/xx unknown
- 1972-03-04 IT IT21447/72A patent/IT953441B/it active
- 1972-03-06 DE DE19722210654 patent/DE2210654A1/de active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0134198A1 (de) * | 1983-08-10 | 1985-03-13 | Ciba-Geigy Ag | Verwendung von Chinonderivaten zum Schützen von Kulturpflanzen vor der phytotoxischen Wirkung von Herbiziden |
| WO1994017070A1 (de) * | 1993-01-20 | 1994-08-04 | Basf Aktiengesellschaft | Derivate des azaanthrachinons und des azaxanthons und diese enthaltende herbizide und pflanzenwachstumsregulatoren |
Also Published As
| Publication number | Publication date |
|---|---|
| IT953441B (it) | 1973-08-10 |
| FR2128591A1 (enExample) | 1972-10-20 |
| CA974520A (en) | 1975-09-16 |
| GB1382721A (en) | 1975-02-05 |
| JPS5231011B1 (enExample) | 1977-08-12 |
| BE780206A (fr) | 1972-09-04 |
| ZA721148B (en) | 1972-10-25 |
| NL7202877A (enExample) | 1972-09-07 |
| IL38840A0 (en) | 1972-04-27 |
| FR2128591B1 (enExample) | 1976-06-11 |
| CH566718A5 (enExample) | 1975-09-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHW | Rejection |