IL102680A - 2) 2 chloro 3 ethoxy 4 ethyl sulfonylbenzoyl (5 methyl 3,1 cyclohexanediol and herbicides containing it - Google Patents
2) 2 chloro 3 ethoxy 4 ethyl sulfonylbenzoyl (5 methyl 3,1 cyclohexanediol and herbicides containing itInfo
- Publication number
- IL102680A IL102680A IL10268092A IL10268092A IL102680A IL 102680 A IL102680 A IL 102680A IL 10268092 A IL10268092 A IL 10268092A IL 10268092 A IL10268092 A IL 10268092A IL 102680 A IL102680 A IL 102680A
- Authority
- IL
- Israel
- Prior art keywords
- chloro
- methyl
- herbicidal
- ethoxy
- compound
- Prior art date
Links
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 34
- 239000000203 mixture Substances 0.000 title claims description 40
- WPGRZNRGTBYDND-UHFFFAOYSA-N (2-chloro-3-ethoxy-4-ethylsulfonylphenyl)-(2,6-dihydroxy-4-methylcyclohexyl)methanone Chemical compound ClC1=C(C(=O)C2C(CC(CC2O)C)O)C=CC(=C1OCC)S(=O)(=O)CC WPGRZNRGTBYDND-UHFFFAOYSA-N 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims description 6
- JHNVAGCOUOBGJS-UHFFFAOYSA-N 2-(2-chloro-3-ethoxy-4-ethylsulfonylbenzoyl)-5-methylcyclohexane-1,3-dione Chemical compound C1=C(S(=O)(=O)CC)C(OCC)=C(Cl)C(C(=O)C2C(CC(C)CC2=O)=O)=C1 JHNVAGCOUOBGJS-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 31
- 239000004009 herbicide Substances 0.000 abstract description 9
- -1 2-chloro-3-ethoxy-4- ethylsulfonylbenzoyl Chemical group 0.000 description 21
- 239000002585 base Substances 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
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- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
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- KNGWEAQJZJKFLI-UHFFFAOYSA-N 2,2-dimethyl-4h-1,3-benzodioxine-6-carbaldehyde Chemical compound O=CC1=CC=C2OC(C)(C)OCC2=C1 KNGWEAQJZJKFLI-UHFFFAOYSA-N 0.000 description 1
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- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- NSOBKQDDAMXWKA-UHFFFAOYSA-N 2-[2-[5-(trifluoromethyl)pyridin-2-yl]oxyphenoxy]propanoic acid Chemical compound OC(=O)C(C)OC1=CC=CC=C1OC1=CC=C(C(F)(F)F)C=N1 NSOBKQDDAMXWKA-UHFFFAOYSA-N 0.000 description 1
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- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- KIEDNEWSYUYDSN-UHFFFAOYSA-N clomazone Chemical compound O=C1C(C)(C)CON1CC1=CC=CC=C1Cl KIEDNEWSYUYDSN-UHFFFAOYSA-N 0.000 description 1
- 239000011362 coarse particle Substances 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940125961 compound 24 Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 150000004891 diazines Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000011086 glassine Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- ZEKANFGSDXODPD-UHFFFAOYSA-N glyphosate-isopropylammonium Chemical compound CC(C)N.OC(=O)CNCP(O)(O)=O ZEKANFGSDXODPD-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 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
- 229910001411 inorganic cation Inorganic materials 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 239000003621 irrigation water Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 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
- 239000003350 kerosene Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- BMLIZLVNXIYGCK-UHFFFAOYSA-N monuron Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C=C1 BMLIZLVNXIYGCK-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- NVGOPFQZYCNLDU-UHFFFAOYSA-N norflurazon Chemical compound O=C1C(Cl)=C(NC)C=NN1C1=CC=CC(C(F)(F)F)=C1 NVGOPFQZYCNLDU-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 description 1
- 230000035515 penetration Effects 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
- 239000010451 perlite Substances 0.000 description 1
- 235000019362 perlite Nutrition 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical class [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229940051841 polyoxyethylene ether Drugs 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- LCHWKMAWSZDQRD-UHFFFAOYSA-N silylformonitrile Chemical class [SiH3]C#N LCHWKMAWSZDQRD-UHFFFAOYSA-N 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 239000012242 solid toxicant Substances 0.000 description 1
- 231100001112 solid toxicant Toxicity 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical class [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000002426 superphosphate Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 238000012956 testing procedure Methods 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 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
- 238000005303 weighing Methods 0.000 description 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/10—Sulfones; Sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/24—Sulfones; Sulfoxides having sulfone or sulfoxide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73928191A | 1991-08-01 | 1991-08-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL102680A0 IL102680A0 (en) | 1993-01-14 |
| IL102680A true IL102680A (en) | 1998-10-30 |
Family
ID=24971605
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL10268092A IL102680A (en) | 1991-08-01 | 1992-07-30 | 2) 2 chloro 3 ethoxy 4 ethyl sulfonylbenzoyl (5 methyl 3,1 cyclohexanediol and herbicides containing it |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP0641317B1 (cs) |
| JP (1) | JP3176369B2 (cs) |
| CN (1) | CN1035739C (cs) |
| AT (1) | ATE143006T1 (cs) |
| AU (1) | AU658921B2 (cs) |
| CA (1) | CA2114618A1 (cs) |
| CZ (1) | CZ282138B6 (cs) |
| DE (1) | DE69213964T2 (cs) |
| DK (1) | DK0641317T3 (cs) |
| IL (1) | IL102680A (cs) |
| MX (1) | MX9204496A (cs) |
| SK (1) | SK239692A3 (cs) |
| WO (1) | WO1993003009A1 (cs) |
| ZA (1) | ZA925775B (cs) |
| ZM (1) | ZM5092A1 (cs) |
| ZW (1) | ZW12492A1 (cs) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4780127A (en) * | 1982-03-25 | 1988-10-25 | Stauffer Chemical Company | Certain 2-(substituted benzoyl)-1,3-cyclohexanediones and their use as herbicides |
| US4957538A (en) * | 1988-11-18 | 1990-09-18 | Ici Americas Inc. | Certain 2-(2',3',4'-trisubstituted benzoyl)-1,3-cyclohexanediones |
-
1992
- 1992-07-29 DK DK92916724.5T patent/DK0641317T3/da active
- 1992-07-29 WO PCT/US1992/006276 patent/WO1993003009A1/en active IP Right Grant
- 1992-07-29 AT AT92916724T patent/ATE143006T1/de not_active IP Right Cessation
- 1992-07-29 EP EP92916724A patent/EP0641317B1/en not_active Expired - Lifetime
- 1992-07-29 JP JP50369993A patent/JP3176369B2/ja not_active Expired - Fee Related
- 1992-07-29 CA CA002114618A patent/CA2114618A1/en not_active Abandoned
- 1992-07-29 ZM ZM5092A patent/ZM5092A1/xx unknown
- 1992-07-29 AU AU23997/92A patent/AU658921B2/en not_active Ceased
- 1992-07-29 DE DE69213964T patent/DE69213964T2/de not_active Expired - Fee Related
- 1992-07-30 IL IL10268092A patent/IL102680A/en not_active IP Right Cessation
- 1992-07-31 MX MX9204496A patent/MX9204496A/es not_active IP Right Cessation
- 1992-07-31 ZA ZA925775A patent/ZA925775B/xx unknown
- 1992-07-31 ZW ZW124/92A patent/ZW12492A1/xx unknown
- 1992-07-31 SK SK2396-92A patent/SK239692A3/sk unknown
- 1992-07-31 CZ CS922396A patent/CZ282138B6/cs not_active IP Right Cessation
- 1992-08-01 CN CN92108999A patent/CN1035739C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| AU658921B2 (en) | 1995-05-04 |
| CZ282138B6 (cs) | 1997-05-14 |
| ZM5092A1 (en) | 1994-04-25 |
| ATE143006T1 (de) | 1996-10-15 |
| IL102680A0 (en) | 1993-01-14 |
| MX9204496A (es) | 1993-03-01 |
| AU2399792A (en) | 1993-03-02 |
| CN1035739C (zh) | 1997-09-03 |
| ZW12492A1 (en) | 1993-04-14 |
| DE69213964D1 (de) | 1996-10-24 |
| WO1993003009A1 (en) | 1993-02-18 |
| CN1070638A (zh) | 1993-04-07 |
| DE69213964T2 (de) | 1997-02-06 |
| DK0641317T3 (da) | 1997-01-13 |
| SK239692A3 (en) | 1995-07-11 |
| ZA925775B (en) | 1993-04-28 |
| EP0641317A1 (en) | 1995-03-08 |
| CZ239692A3 (en) | 1993-02-17 |
| JPH07500818A (ja) | 1995-01-26 |
| CA2114618A1 (en) | 1993-02-18 |
| JP3176369B2 (ja) | 2001-06-18 |
| EP0641317B1 (en) | 1996-09-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| HP | Change in proprietorship | ||
| MM9K | Patent not in force due to non-payment of renewal fees | ||
| HC | Change of name of proprietor(s) |