DE2544367A1 - 3-alkyl- bzw. -cycloalkylisoxazol- derivate - Google Patents
3-alkyl- bzw. -cycloalkylisoxazol- derivateInfo
- Publication number
- DE2544367A1 DE2544367A1 DE19752544367 DE2544367A DE2544367A1 DE 2544367 A1 DE2544367 A1 DE 2544367A1 DE 19752544367 DE19752544367 DE 19752544367 DE 2544367 A DE2544367 A DE 2544367A DE 2544367 A1 DE2544367 A1 DE 2544367A1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- butyl
- isoxazolyl
- tert
- urea
- 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.)
- Ceased
Links
- 150000001875 compounds Chemical class 0.000 claims description 25
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 23
- -1 morpholino, pyrrolidino Chemical group 0.000 claims description 21
- 239000004202 carbamide Substances 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 239000004009 herbicide Substances 0.000 claims description 7
- SCMVCKIBKAYNGT-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-methylurea Chemical compound CNC(=O)NC1=CC(C(C)(C)C)=NO1 SCMVCKIBKAYNGT-UHFFFAOYSA-N 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- CVYPCXPTUOOTDX-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-1,3-dimethylurea Chemical compound CNC(=O)N(C)C1=CC(C(C)(C)C)=NO1 CVYPCXPTUOOTDX-UHFFFAOYSA-N 0.000 claims description 3
- TUUQZYVMMHAPRI-UHFFFAOYSA-N methyl n-(3-tert-butyl-4-chloro-1,2-oxazol-5-yl)carbamate Chemical compound COC(=O)NC=1ON=C(C(C)(C)C)C=1Cl TUUQZYVMMHAPRI-UHFFFAOYSA-N 0.000 claims description 3
- YLKNELCNPDKQIL-UHFFFAOYSA-N 1-(3-tert-butyl-4-chloro-1,2-oxazol-5-yl)-3-methylurea Chemical compound CNC(=O)NC=1ON=C(C(C)(C)C)C=1Cl YLKNELCNPDKQIL-UHFFFAOYSA-N 0.000 claims description 2
- KMEKZESIISVXOI-UHFFFAOYSA-N 1-butyl-3-(3-tert-butyl-1,2-oxazol-5-yl)-1-methylurea Chemical compound CCCCN(C)C(=O)NC1=CC(C(C)(C)C)=NO1 KMEKZESIISVXOI-UHFFFAOYSA-N 0.000 claims description 2
- LJXLRUOXUFVORK-UHFFFAOYSA-N 3-(4-bromo-3-tert-butyl-1,2-oxazol-5-yl)-1,1-dimethylurea Chemical compound CN(C)C(=O)NC=1ON=C(C(C)(C)C)C=1Br LJXLRUOXUFVORK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 21
- 125000000217 alkyl group Chemical group 0.000 claims 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 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
- 239000011541 reaction mixture Substances 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 241000196324 Embryophyta Species 0.000 description 7
- 230000002363 herbicidal effect Effects 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- IAXWZYXUKABJAN-UHFFFAOYSA-N 1,2-oxazol-5-amine Chemical compound NC1=CC=NO1 IAXWZYXUKABJAN-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- PNHJSONCSFWVTK-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-1,3,3-trimethylurea Chemical compound CN(C)C(=O)N(C)C1=CC(C(C)(C)C)=NO1 PNHJSONCSFWVTK-UHFFFAOYSA-N 0.000 description 3
- QBVVHKDTQWZQJB-UHFFFAOYSA-N 3-(3-tert-butyl-1,2-oxazol-5-yl)-1,1-dimethylurea Chemical compound CN(C)C(=O)NC1=CC(C(C)(C)C)=NO1 QBVVHKDTQWZQJB-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 244000098338 Triticum aestivum Species 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 235000019988 mead Nutrition 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- AHBATNRNNHRAAR-UHFFFAOYSA-N 3-tert-butyl-5-isocyanato-1,2-oxazole Chemical compound CC(C)(C)C=1C=C(N=C=O)ON=1 AHBATNRNNHRAAR-UHFFFAOYSA-N 0.000 description 2
- XSQALNWVNGTOBH-UHFFFAOYSA-N 5-isocyanato-1,2-oxazole Chemical compound O=C=NC1=CC=NO1 XSQALNWVNGTOBH-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 244000237956 Amaranthus retroflexus Species 0.000 description 2
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 2
- 235000005637 Brassica campestris Nutrition 0.000 description 2
- 241001301148 Brassica rapa subsp. oleifera Species 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- 240000003176 Digitaria ciliaris Species 0.000 description 2
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 244000088461 Panicum crus-galli Species 0.000 description 2
- 235000011999 Panicum crusgalli Nutrition 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 229920005551 calcium lignosulfonate Polymers 0.000 description 2
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- LJFLSSVKLBCDNE-UHFFFAOYSA-N 1,1-dimethyl-3-(3-propyl-1,2-oxazol-5-yl)urea Chemical compound CCCC=1C=C(NC(=O)N(C)C)ON=1 LJFLSSVKLBCDNE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LTSMPRQQQRFLTH-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-methylthiourea Chemical compound CNC(=S)NC1=CC(C(C)(C)C)=NO1 LTSMPRQQQRFLTH-UHFFFAOYSA-N 0.000 description 1
- APHNQOGPYLTSFX-UHFFFAOYSA-N 3-tert-butyl-1,2-oxazol-5-amine Chemical compound CC(C)(C)C=1C=C(N)ON=1 APHNQOGPYLTSFX-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
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- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
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- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
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- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
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- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UJXBZCDDWHNWNG-UHFFFAOYSA-N butyl thiohypochlorite Chemical compound CCCCSCl UJXBZCDDWHNWNG-UHFFFAOYSA-N 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
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- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 235000001050 hortel pimenta Nutrition 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 125000000842 isoxazolyl group Chemical group 0.000 description 1
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- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 description 1
- NIGVNKDENQWICK-UHFFFAOYSA-N methyl n-(3-tert-butyl-1,2-oxazol-5-yl)carbamate Chemical compound COC(=O)NC1=CC(C(C)(C)C)=NO1 NIGVNKDENQWICK-UHFFFAOYSA-N 0.000 description 1
- CYTNPFQEAMQWCL-UHFFFAOYSA-N n-methyl-1,2-oxazol-5-amine Chemical compound CNC1=CC=NO1 CYTNPFQEAMQWCL-UHFFFAOYSA-N 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachloro-phenol Natural products OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical class OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 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
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/14—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/20—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings condensed with carbocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP49114839A JPS5810361B2 (ja) | 1974-10-04 | 1974-10-04 | ３−アルチルイソオキサゾ−ル系除草剤 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2544367A1 true DE2544367A1 (de) | 1976-04-22 |
Family
ID=14647980
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752544367 Ceased DE2544367A1 (de) | 1974-10-04 | 1975-10-03 | 3-alkyl- bzw. -cycloalkylisoxazol- derivate |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4028376A (enExample) |
| JP (1) | JPS5810361B2 (enExample) |
| AR (1) | AR220094A1 (enExample) |
| BR (1) | BR7506453A (enExample) |
| CA (1) | CA1049516A (enExample) |
| CH (1) | CH595762A5 (enExample) |
| DE (1) | DE2544367A1 (enExample) |
| DK (1) | DK144526C (enExample) |
| FR (1) | FR2286820A1 (enExample) |
| GB (1) | GB1463439A (enExample) |
| IT (1) | IT1047275B (enExample) |
| MX (1) | MX3245E (enExample) |
| NL (1) | NL7511694A (enExample) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2818947A1 (de) * | 1977-04-28 | 1978-11-02 | Shionogi & Co | Verfahren zur herstellung von harnstoffderivaten |
| EP0002881A1 (en) * | 1977-11-02 | 1979-07-11 | FISONS plc | 5-Isoxazolylurea derivatives, their preparation, their use and compositions containing them |
| EP0010262A1 (en) * | 1978-10-12 | 1980-04-30 | Shionogi & Co., Ltd. | Process for preparing 3-amino-5-t-butylisoxazole |
| DE3940261A1 (de) * | 1989-12-06 | 1991-06-13 | Agrolinz Agrarchemikalien Muen | Verfahren zur herstellung reiner, unsymmetrisch disubstituierter harnstoffe |
| US5099021A (en) * | 1989-11-10 | 1992-03-24 | Agrolinz Agrarchemikalien Gesellschaft M.B.H. | Process for the preparation of pure, unsymmetrically disubstituted ureas |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4111680A (en) * | 1973-07-27 | 1978-09-05 | Shionogi & Co., Ltd. | Herbicidal compositions containing 3-isoxazolylurea derivatives |
| JPS5031039A (enExample) * | 1973-07-27 | 1975-03-27 | ||
| FR2392981A1 (fr) * | 1977-05-31 | 1978-12-29 | Philagro Sa | Thiolcarbamates d'(isoxazolyl)-alcoyles et compositions herbicides les contenant |
| US4336264A (en) * | 1980-06-19 | 1982-06-22 | Eli Lilly And Company | 1-Benzoyl-3-(isoxazolyl or benzisoxazolyl)-ureas and insecticidal use thereof |
| US4394510A (en) * | 1981-02-02 | 1983-07-19 | Eli Lilly And Company | Process for preparing an isoxazolylurea |
| IT1163183B (it) * | 1983-03-29 | 1987-04-08 | Anic Spa | Composti eterociclici ad attivita' erbicida |
| US4689071A (en) * | 1983-05-05 | 1987-08-25 | Ppg Industries, Inc. | Herbicidally active 3-isoxazolyl-2-imidazolidinone derivatives |
| US4544753A (en) * | 1984-05-31 | 1985-10-01 | Hoechst-Roussel Pharmaceuticals Incorporated | Isoxazole intermediates |
| DE3818556A1 (de) * | 1988-06-01 | 1989-12-07 | Pfeiffer Vakuumtechnik | Magnetlager fuer eine schnell rotierende vakuumpumpe |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3547940A (en) * | 1967-10-31 | 1970-12-15 | Du Pont | Substituted ureido isoxazoles |
| US3743498A (en) * | 1967-10-31 | 1973-07-03 | Du Pont | Method of selectively controlling undesirable vegetation |
-
1974
- 1974-10-04 JP JP49114839A patent/JPS5810361B2/ja not_active Expired
-
1975
- 1975-09-23 US US05/615,883 patent/US4028376A/en not_active Expired - Lifetime
- 1975-09-26 CA CA236,477A patent/CA1049516A/en not_active Expired
- 1975-10-01 DK DK443575A patent/DK144526C/da not_active IP Right Cessation
- 1975-10-01 GB GB4020575A patent/GB1463439A/en not_active Expired
- 1975-10-03 AR AR260670A patent/AR220094A1/es active
- 1975-10-03 NL NL7511694A patent/NL7511694A/xx not_active Application Discontinuation
- 1975-10-03 DE DE19752544367 patent/DE2544367A1/de not_active Ceased
- 1975-10-03 FR FR7530435A patent/FR2286820A1/fr active Granted
- 1975-10-03 BR BR7506453*A patent/BR7506453A/pt unknown
- 1975-10-03 MX MX000867U patent/MX3245E/es unknown
- 1975-10-03 IT IT69469/75A patent/IT1047275B/it active
- 1975-10-03 CH CH1289575A patent/CH595762A5/xx not_active IP Right Cessation
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2818947A1 (de) * | 1977-04-28 | 1978-11-02 | Shionogi & Co | Verfahren zur herstellung von harnstoffderivaten |
| EP0002881A1 (en) * | 1977-11-02 | 1979-07-11 | FISONS plc | 5-Isoxazolylurea derivatives, their preparation, their use and compositions containing them |
| EP0010262A1 (en) * | 1978-10-12 | 1980-04-30 | Shionogi & Co., Ltd. | Process for preparing 3-amino-5-t-butylisoxazole |
| US5099021A (en) * | 1989-11-10 | 1992-03-24 | Agrolinz Agrarchemikalien Gesellschaft M.B.H. | Process for the preparation of pure, unsymmetrically disubstituted ureas |
| DE3940261A1 (de) * | 1989-12-06 | 1991-06-13 | Agrolinz Agrarchemikalien Muen | Verfahren zur herstellung reiner, unsymmetrisch disubstituierter harnstoffe |
Also Published As
| Publication number | Publication date |
|---|---|
| AR220094A1 (es) | 1980-10-15 |
| CH595762A5 (enExample) | 1978-02-28 |
| GB1463439A (enExample) | 1977-02-02 |
| MX3245E (es) | 1980-08-06 |
| AU8551475A (en) | 1977-04-21 |
| NL7511694A (nl) | 1976-04-06 |
| FR2286820A1 (fr) | 1976-04-30 |
| DK144526C (da) | 1982-10-04 |
| BR7506453A (pt) | 1976-08-10 |
| JPS5810361B2 (ja) | 1983-02-25 |
| IT1047275B (it) | 1980-09-10 |
| DK443575A (da) | 1976-04-05 |
| DK144526B (da) | 1982-03-22 |
| FR2286820B1 (enExample) | 1979-04-20 |
| JPS5141431A (enExample) | 1976-04-07 |
| US4028376A (en) | 1977-06-07 |
| CA1049516A (en) | 1979-02-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8131 | Rejection |