DE3032973A1 - Cyclohexan-1,3-dion-derivate - Google Patents
Cyclohexan-1,3-dion-derivateInfo
- Publication number
- DE3032973A1 DE3032973A1 DE19803032973 DE3032973A DE3032973A1 DE 3032973 A1 DE3032973 A1 DE 3032973A1 DE 19803032973 DE19803032973 DE 19803032973 DE 3032973 A DE3032973 A DE 3032973A DE 3032973 A1 DE3032973 A1 DE 3032973A1
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- acid
- salts
- parts
- chloro
- 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- Withdrawn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
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical class O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 title abstract description 4
- 150000003839 salts Chemical group 0.000 claims abstract description 59
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 239000004009 herbicide Substances 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 claims abstract description 3
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims abstract description 3
- 125000000262 haloalkenyl group Chemical group 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000003513 alkali Substances 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 5
- 230000002363 herbicidal effect Effects 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000003868 ammonium compounds Chemical class 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- -1 ethoxyaminobutylidene Chemical group 0.000 description 62
- 150000002148 esters Chemical class 0.000 description 33
- 150000001408 amides Chemical class 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 239000002253 acid Substances 0.000 description 15
- 239000004480 active ingredient Substances 0.000 description 15
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 159000000000 sodium salts Chemical class 0.000 description 12
- 239000003921 oil Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 240000007594 Oryza sativa Species 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 235000007164 Oryza sativa Nutrition 0.000 description 8
- 239000004202 carbamide Substances 0.000 description 8
- 235000013877 carbamide Nutrition 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
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- 229940125904 compound 1 Drugs 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 6
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- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 244000046052 Phaseolus vulgaris Species 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
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- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 5
- 150000004702 methyl esters Chemical class 0.000 description 5
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
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- 150000001242 acetic acid derivatives Chemical class 0.000 description 4
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- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
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- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
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- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical class CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 2
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- HCJLVWUMMKIQIM-UHFFFAOYSA-M sodium;2,3,4,5,6-pentachlorophenolate Chemical compound [Na+].[O-]C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl HCJLVWUMMKIQIM-UHFFFAOYSA-M 0.000 description 1
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- RJKCKKDSSSRYCB-UHFFFAOYSA-N tebutam Chemical compound CC(C)(C)C(=O)N(C(C)C)CC1=CC=CC=C1 RJKCKKDSSSRYCB-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 125000004035 thiopropyl group Chemical group [H]SC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
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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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Environmental Sciences (AREA)
- Wood Science & Technology (AREA)
- Pest Control & Pesticides (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Steroid Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803032973 DE3032973A1 (de) | 1980-09-02 | 1980-09-02 | Cyclohexan-1,3-dion-derivate |
| AT81105558T ATE6636T1 (de) | 1980-09-02 | 1981-07-15 | Cyclohexan-1,3-dion-derivate. |
| EP81105558A EP0046860B1 (de) | 1980-09-02 | 1981-07-15 | Cyclohexan-1,3-dion-Derivate |
| DE8181105558T DE3162656D1 (en) | 1980-09-02 | 1981-07-15 | Cyclohexane-1,3-dione derivatives |
| GR65591A GR74305B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-09-02 | 1981-07-22 | |
| IL63597A IL63597A (en) | 1980-09-02 | 1981-08-17 | Cyclohexane-1,3-dione derivatives,their preparation and their use as herbicides |
| CA000384496A CA1167466A (en) | 1980-09-02 | 1981-08-24 | Cyclohexane-1,3-dione derivatives |
| IE1961/81A IE51575B1 (en) | 1980-09-02 | 1981-08-27 | Cyclohexane-1,3-dione derivatives |
| CS816446A CS226035B2 (en) | 1980-09-02 | 1981-08-31 | Herbicide |
| BR8105587A BR8105587A (pt) | 1980-09-02 | 1981-09-01 | Composicoes herbicidas d base de derviados de ciclo-hexano1,3-diona |
| DK386281A DK153835C (da) | 1980-09-02 | 1981-09-01 | Cyclohexan-1,3-dion-derivater, herbicid og fremgangsmaade til bekaempelse af uoenskede planter |
| ZA816048A ZA816048B (en) | 1980-09-02 | 1981-09-01 | Cyclohexane-1,3-dione derivatives |
| AU74879/81A AU543509B2 (en) | 1980-09-02 | 1981-09-02 | Cyclohexane 1,3-diones of amino-oxy ethers |
| JP56137152A JPS5777645A (en) | 1980-09-02 | 1981-09-02 | Cyclohexane-1,3-dione derivative and herbicide containing same |
| DD81232676A DD200141A5 (de) | 1980-09-02 | 1981-09-19 | Herbizide mittel |
| US06/498,043 US4568383A (en) | 1980-09-02 | 1983-05-25 | Cyclohexane-1,3-dione derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803032973 DE3032973A1 (de) | 1980-09-02 | 1980-09-02 | Cyclohexan-1,3-dion-derivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3032973A1 true DE3032973A1 (de) | 1982-04-22 |
Family
ID=6110917
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803032973 Withdrawn DE3032973A1 (de) | 1980-09-02 | 1980-09-02 | Cyclohexan-1,3-dion-derivate |
| DE8181105558T Expired DE3162656D1 (en) | 1980-09-02 | 1981-07-15 | Cyclohexane-1,3-dione derivatives |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8181105558T Expired DE3162656D1 (en) | 1980-09-02 | 1981-07-15 | Cyclohexane-1,3-dione derivatives |
Country Status (15)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0172502A1 (de) * | 1984-08-18 | 1986-02-26 | BASF Aktiengesellschaft | Cyclohexenonderivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchses |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE32489E (en) * | 1980-11-25 | 1987-09-01 | Chevron Research Company | Herbicidal substituted 2-(1-(oxyamino)-alkylidene)-cyclohexane-1,3-diones |
| US4440566A (en) * | 1982-08-05 | 1984-04-03 | Chevron Research Company | Herbicidal substituted 2-(1-(oxyamino)-alkylidene)-cyclohexane-1,3-diones |
| DE3219315A1 (de) * | 1982-05-22 | 1983-11-24 | Basf Ag, 6700 Ludwigshafen | Cyclohexan-1,3-dion-derivate |
| DE3239071A1 (de) * | 1982-10-22 | 1984-04-26 | Basf Ag, 6700 Ludwigshafen | Cyclohexan-1,3-dionderivate, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses |
| JPS59196840A (ja) * | 1983-04-22 | 1984-11-08 | Kumiai Chem Ind Co Ltd | シクロヘキサン誘導体および植物生長調節剤 |
| US4626276A (en) * | 1984-06-11 | 1986-12-02 | Chevron Research Company | Herbicidal trans-2-[(3-chloroallyloxyimino)alkyl]-5-(substitutedsulfinylalkyl)-cyclohexane-1,3-diones and derivatives thereof |
| DE3440410A1 (de) * | 1984-11-06 | 1986-05-07 | Basf Ag, 6700 Ludwigshafen | Cyclohexenonderivate, verfahren zu ihrer herstellung sowie ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses |
| US4838932A (en) * | 1987-08-20 | 1989-06-13 | Stauffer Chemical Company | Certain 2-(2-substituted benzoyl)-4-(substituted imino, oximino or carbonyl)-1,3-cyclohexanediones |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2251544B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1973-11-21 | 1978-04-21 | Rhone Poulenc Ind | |
| US3950420A (en) * | 1973-08-15 | 1976-04-13 | Nippon Soda Company, Ltd. | Cyclohexane derivatives |
| IL54560A (en) * | 1977-05-23 | 1981-06-29 | Nippon Soda Co | Substituted 2-aminoalkylidene-1,3-cyclohexanediones,their preparation and their use as herbicides |
| JPS6045633B2 (ja) * | 1977-07-15 | 1985-10-11 | 日本曹達株式会社 | シクロヘキサン誘導体、製造方法及び除草剤 |
-
1980
- 1980-09-02 DE DE19803032973 patent/DE3032973A1/de not_active Withdrawn
-
1981
- 1981-07-15 EP EP81105558A patent/EP0046860B1/de not_active Expired
- 1981-07-15 AT AT81105558T patent/ATE6636T1/de not_active IP Right Cessation
- 1981-07-15 DE DE8181105558T patent/DE3162656D1/de not_active Expired
- 1981-07-22 GR GR65591A patent/GR74305B/el unknown
- 1981-08-17 IL IL63597A patent/IL63597A/xx unknown
- 1981-08-24 CA CA000384496A patent/CA1167466A/en not_active Expired
- 1981-08-27 IE IE1961/81A patent/IE51575B1/en unknown
- 1981-08-31 CS CS816446A patent/CS226035B2/cs unknown
- 1981-09-01 DK DK386281A patent/DK153835C/da not_active IP Right Cessation
- 1981-09-01 ZA ZA816048A patent/ZA816048B/xx unknown
- 1981-09-01 BR BR8105587A patent/BR8105587A/pt unknown
- 1981-09-02 AU AU74879/81A patent/AU543509B2/en not_active Ceased
- 1981-09-02 JP JP56137152A patent/JPS5777645A/ja active Pending
- 1981-09-19 DD DD81232676A patent/DD200141A5/de not_active IP Right Cessation
-
1983
- 1983-05-25 US US06/498,043 patent/US4568383A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0172502A1 (de) * | 1984-08-18 | 1986-02-26 | BASF Aktiengesellschaft | Cyclohexenonderivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchses |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE6636T1 (de) | 1984-03-15 |
| ZA816048B (en) | 1982-09-29 |
| DK153835B (da) | 1988-09-12 |
| CA1167466A (en) | 1984-05-15 |
| DK386281A (da) | 1982-03-03 |
| IE51575B1 (en) | 1987-01-21 |
| JPS5777645A (en) | 1982-05-15 |
| IL63597A (en) | 1985-06-30 |
| US4568383A (en) | 1986-02-04 |
| GR74305B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-06-22 |
| AU7487981A (en) | 1982-03-11 |
| EP0046860A1 (de) | 1982-03-10 |
| DD200141A5 (de) | 1983-03-23 |
| IL63597A0 (en) | 1981-11-30 |
| IE811961L (en) | 1982-03-02 |
| AU543509B2 (en) | 1985-04-26 |
| DE3162656D1 (en) | 1984-04-19 |
| BR8105587A (pt) | 1982-05-18 |
| CS226035B2 (en) | 1984-03-19 |
| EP0046860B1 (de) | 1984-03-14 |
| DK153835C (da) | 1989-01-30 |
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| 8130 | Withdrawal |