IL87427A - 5-Heterocyclic-substituted oxazolidine dihaloacetamides and compositions containing them - Google Patents
5-Heterocyclic-substituted oxazolidine dihaloacetamides and compositions containing themInfo
- Publication number
- IL87427A IL87427A IL8742788A IL8742788A IL87427A IL 87427 A IL87427 A IL 87427A IL 8742788 A IL8742788 A IL 8742788A IL 8742788 A IL8742788 A IL 8742788A IL 87427 A IL87427 A IL 87427A
- Authority
- IL
- Israel
- Prior art keywords
- rate
- methyl
- dote
- barnyard
- grass
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 84
- 150000002917 oxazolidines Chemical class 0.000 title description 4
- 235000011684 Sorghum saccharatum Nutrition 0.000 claims description 347
- 240000008042 Zea mays Species 0.000 claims description 254
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 254
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 254
- 235000005822 corn Nutrition 0.000 claims description 254
- 244000068988 Glycine max Species 0.000 claims description 192
- 235000010469 Glycine max Nutrition 0.000 claims description 192
- 230000002363 herbicidal effect Effects 0.000 claims description 159
- 235000021307 Triticum Nutrition 0.000 claims description 149
- 150000001875 compounds Chemical class 0.000 claims description 145
- 239000004009 herbicide Substances 0.000 claims description 136
- -1 hetero cyclic radical Chemical class 0.000 claims description 79
- 238000000034 method Methods 0.000 claims description 76
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims description 48
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 31
- 244000038559 crop plants Species 0.000 claims description 29
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 28
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 26
- 230000002605 anti-dotal effect Effects 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
- 125000005842 heteroatom Chemical group 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 claims description 16
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 claims description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 239000001301 oxygen Substances 0.000 claims description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 claims description 14
- 239000005711 Benzoic acid Substances 0.000 claims description 13
- 235000010233 benzoic acid Nutrition 0.000 claims description 13
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 13
- 235000001968 nicotinic acid Nutrition 0.000 claims description 13
- 229960003512 nicotinic acid Drugs 0.000 claims description 13
- 239000011664 nicotinic acid Substances 0.000 claims description 13
- 125000000160 oxazolidinyl group Chemical group 0.000 claims description 13
- 150000003254 radicals Chemical class 0.000 claims description 13
- 150000004702 methyl esters Chemical class 0.000 claims description 12
- VTNQPKFIQCLBDU-UHFFFAOYSA-N Acetochlor Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1CC VTNQPKFIQCLBDU-UHFFFAOYSA-N 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000001188 haloalkyl group Chemical group 0.000 claims description 10
- 229960001413 acetanilide Drugs 0.000 claims description 9
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 claims description 8
- QXDOFVVNXBGLKK-UHFFFAOYSA-N 3-Isoxazolidinone Chemical compound OC1=NOCC1 QXDOFVVNXBGLKK-UHFFFAOYSA-N 0.000 claims description 8
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- STEPQTYSZVCJPV-UHFFFAOYSA-N metazachlor Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)CN1N=CC=C1 STEPQTYSZVCJPV-UHFFFAOYSA-N 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 claims description 7
- HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 claims description 6
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 6
- GUVLYNGULCJVDO-UHFFFAOYSA-N EPTC Chemical group CCCN(CCC)C(=O)SCC GUVLYNGULCJVDO-UHFFFAOYSA-N 0.000 claims description 6
- 240000006394 Sorghum bicolor Species 0.000 claims description 6
- 229940100389 Sulfonylurea Drugs 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- 231100000674 Phytotoxicity Toxicity 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000002147 dimethylamino group Chemical class [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- YGTYRMDZBFYUCE-UHFFFAOYSA-N 2-chloro-n-(2-methoxy-6-methylphenyl)-n-(propan-2-yloxymethyl)acetamide Chemical compound COC1=CC=CC(C)=C1N(COC(C)C)C(=O)CCl YGTYRMDZBFYUCE-UHFFFAOYSA-N 0.000 claims description 3
- KTFNPLHWDYECSQ-UHFFFAOYSA-N 2-chloro-n-(ethoxymethyl)-n-[2-methyl-6-(trifluoromethyl)phenyl]acetamide Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1C(F)(F)F KTFNPLHWDYECSQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 150000003863 ammonium salts Chemical class 0.000 claims description 3
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 claims description 3
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 3
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- UIWOZHBYBSGCOS-UHFFFAOYSA-N methoxy(oxido)phosphanium Chemical compound CO[PH2]=O UIWOZHBYBSGCOS-UHFFFAOYSA-N 0.000 claims description 3
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 claims description 3
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 claims description 3
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 claims description 3
- 125000006012 2-chloroethoxy group Chemical group 0.000 claims description 2
- DLXUBTVMCYYDGS-UHFFFAOYSA-N C1=C([N+]([O-])=O)C(C(=O)OCC)=C(OCC)C(OC=2C(=C(N(C)N=2)C(F)(F)F)Cl)=C1 Chemical compound C1=C([N+]([O-])=O)C(C(=O)OCC)=C(OCC)C(OC=2C(=C(N(C)N=2)C(F)(F)F)Cl)=C1 DLXUBTVMCYYDGS-UHFFFAOYSA-N 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 5
- 239000011593 sulfur Substances 0.000 claims 5
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims 4
- ZJULYDCRWUEPTK-UHFFFAOYSA-N dichloromethyl Chemical compound Cl[CH]Cl ZJULYDCRWUEPTK-UHFFFAOYSA-N 0.000 claims 3
- 125000004970 halomethyl group Chemical group 0.000 claims 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims 2
- SLAMLWHELXOEJZ-UHFFFAOYSA-N 2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-N 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- SUSRORUBZHMPCO-UHFFFAOYSA-N MC-4379 Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 SUSRORUBZHMPCO-UHFFFAOYSA-N 0.000 claims 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 239000004202 carbamide Substances 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 150000003951 lactams Chemical class 0.000 claims 2
- LZGUHMNOBNWABZ-UHFFFAOYSA-N n-nitro-n-phenylnitramide Chemical compound [O-][N+](=O)N([N+]([O-])=O)C1=CC=CC=C1 LZGUHMNOBNWABZ-UHFFFAOYSA-N 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 claims 1
- ZBMRKNMTMPPMMK-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid;azane Chemical compound [NH4+].CP(O)(=O)CCC(N)C([O-])=O ZBMRKNMTMPPMMK-UHFFFAOYSA-N 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- WYFCZWSWFGJODV-MIANJLSGSA-N 4-[[(1s)-2-[(e)-3-[3-chloro-2-fluoro-6-(tetrazol-1-yl)phenyl]prop-2-enoyl]-5-(4-methyl-2-oxopiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-1-carbonyl]amino]benzoic acid Chemical compound O=C1CN(C)CCN1C1=CC=CC2=C1CCN(C(=O)\C=C\C=1C(=CC=C(Cl)C=1F)N1N=NN=C1)[C@@H]2C(=O)NC1=CC=C(C(O)=O)C=C1 WYFCZWSWFGJODV-MIANJLSGSA-N 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 1
- 244000098338 Triticum aestivum Species 0.000 claims 1
- 235000010716 Vigna mungo Nutrition 0.000 claims 1
- 240000001417 Vigna umbellata Species 0.000 claims 1
- 235000011453 Vigna umbellata Nutrition 0.000 claims 1
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 claims 1
- ZQOKGFJVSMHJSW-UHFFFAOYSA-N dimethyl 2-(difluoromethyl)-4-(2-methylpropyl)-6-(trifluoromethyl)pyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C(F)F)N=C(C(F)(F)F)C(C(=O)OC)=C1CC(C)C ZQOKGFJVSMHJSW-UHFFFAOYSA-N 0.000 claims 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 claims 1
- GVBSRTBYUFJDIW-UHFFFAOYSA-N pyridine-3,5-dicarbothioic s-acid Chemical compound OC(=S)C1=CN=CC(C(O)=S)=C1 GVBSRTBYUFJDIW-UHFFFAOYSA-N 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 424
- 230000000694 effects Effects 0.000 description 376
- 230000005764 inhibitory process Effects 0.000 description 373
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- 235000013339 cereals Nutrition 0.000 description 176
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- 235000009344 Chenopodium album Nutrition 0.000 description 175
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- 241000209140 Triticum Species 0.000 description 148
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- 239000000729 antidote Substances 0.000 description 106
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 67
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- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 67
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 67
- 235000014716 Eleusine indica Nutrition 0.000 description 67
- 239000002689 soil Substances 0.000 description 40
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 34
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
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- 239000000047 product Substances 0.000 description 19
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
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- 238000012360 testing method Methods 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
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- 229960005419 nitrogen Drugs 0.000 description 10
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 125000000623 heterocyclic group Chemical group 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 125000001984 thiazolidinyl group Chemical group 0.000 description 8
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- 238000011282 treatment Methods 0.000 description 7
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 6
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
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- 238000003756 stirring Methods 0.000 description 6
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- 238000010626 work up procedure Methods 0.000 description 6
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- 238000007630 basic procedure Methods 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
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- 239000012280 lithium aluminium hydride Substances 0.000 description 5
- 230000001681 protective effect Effects 0.000 description 5
- 241000894007 species Species 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical class C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 4
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical group CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 125000001246 bromo group Chemical group Br* 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 229940093499 ethyl acetate Drugs 0.000 description 4
- 235000019439 ethyl acetate Nutrition 0.000 description 4
- 238000011221 initial treatment Methods 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
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- 230000004044 response Effects 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 230000000007 visual effect Effects 0.000 description 4
- AZVSIHIBYRHSLB-UHFFFAOYSA-N 3-furaldehyde Chemical compound O=CC=1C=COC=1 AZVSIHIBYRHSLB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 235000015505 Sorghum bicolor subsp. bicolor Nutrition 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 3
- 125000004982 dihaloalkyl group Chemical group 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/12—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
-
- 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
- C07D209/56—Ring systems containing three or more rings
- C07D209/96—Spiro-condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/10—Spiro-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Pest Control & Pesticides (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Emergency Lowering Means (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8478687A | 1987-08-13 | 1987-08-13 | |
| US07/212,621 US5225570A (en) | 1987-08-13 | 1988-07-01 | 5-heterocyclic-substituted oxazolidine dihaloacetamides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL87427A0 IL87427A0 (en) | 1989-01-31 |
| IL87427A true IL87427A (en) | 1995-01-24 |
Family
ID=26771426
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL8742788A IL87427A (en) | 1987-08-13 | 1988-08-12 | 5-Heterocyclic-substituted oxazolidine dihaloacetamides and compositions containing them |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US5225570A (en, 2012) |
| EP (1) | EP0304409B1 (en, 2012) |
| JP (1) | JPH0653737B2 (en, 2012) |
| CN (1) | CN1025141C (en, 2012) |
| AU (1) | AU608639B2 (en, 2012) |
| BG (1) | BG49813A3 (en, 2012) |
| BR (1) | BR8804098A (en, 2012) |
| CA (1) | CA1328108C (en, 2012) |
| DE (1) | DE3875556T2 (en, 2012) |
| DK (1) | DK451988A (en, 2012) |
| ES (1) | ES2010153T3 (en, 2012) |
| GR (1) | GR3006869T3 (en, 2012) |
| HU (1) | HU205826B (en, 2012) |
| IL (1) | IL87427A (en, 2012) |
| PL (1) | PL274217A1 (en, 2012) |
| RU (1) | RU2093029C1 (en, 2012) |
| UA (1) | UA35539C2 (en, 2012) |
| YU (1) | YU47061B (en, 2012) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5502025A (en) * | 1987-08-13 | 1996-03-26 | Monsanto Company | Safening herbicidal pyrazolylsulfonylureas |
| US5256625A (en) * | 1987-08-13 | 1993-10-26 | Monsanto Company | Safening imidazolinone herbicides |
| US5256630A (en) * | 1987-08-13 | 1993-10-26 | Monsanto Company | Safening mixtures of sulfonylurea and acetanilide herbicides |
| US5710100A (en) * | 1987-08-13 | 1998-01-20 | Monsanto Company | Safening imidazolinone herbicides |
| YU48319B (sh) * | 1988-08-01 | 1998-05-15 | Monsanto Company | Bezbednosni herbicidni derivati benzoeve kiseline |
| US5880066A (en) * | 1990-12-11 | 1999-03-09 | Monsanto Company | Safened herbicidal sulfonamide compositions |
| US5527762A (en) * | 1990-12-12 | 1996-06-18 | Zeneca Limited | Antidoting herbicidal 3-isoxazolidinone compounds |
| US5691274A (en) * | 1990-12-12 | 1997-11-25 | Zeneca Limited | Antidoting herbicidal 3-isoxazolidinone compounds |
| US5395816A (en) * | 1990-12-12 | 1995-03-07 | Imperial Chemical Industries Plc | Antidoting herbicidal 3-ixoxazolidinone compounds |
| EP0561970B1 (en) * | 1990-12-12 | 1995-01-18 | Zeneca Inc. | Antidoting herbicidal 3-isoxazolidinone compounds |
| US5484760A (en) * | 1990-12-31 | 1996-01-16 | Monsanto Company | Herbicide antidotes as safeners for reducing phytotoxicity resulting from synergistic interaction between herbicides and other pesticides |
| US5541148A (en) * | 1992-07-08 | 1996-07-30 | Ciba-Geigy Corporation | Selective safened herbicidal composition comprising 2-ethoxycarbonyl-3-(4,6-dimethoxypyrimidine-2-yl) oxy-pyridine and an acylsulfamoylphenyl-urea safener |
| US5470741A (en) * | 1992-07-22 | 1995-11-28 | Henkel Corporation | Mutant of Geotrichum candidum which produces novel enzyme system to selectively hydrolyze triglycerides |
| EP0616770B1 (de) | 1993-03-22 | 1999-05-06 | Novartis AG | Selektiv-herbizides Mittel |
| EE9500018A (et) * | 1994-06-03 | 1995-12-15 | Ciba-Geigy Ag | Selektiivne herbitsiid ja meetod selle kasutamiseks |
| US5693590A (en) * | 1994-08-30 | 1997-12-02 | Rohm And Haas Company | Compositions containing phosphosulfonate herbicides and dichloroacetamide safeners |
| ATE171842T1 (de) * | 1994-08-30 | 1998-10-15 | Rohm & Haas | Zusammensetzungen aus phosphosulphonat-herbizide und dichloracetamide-safener und verwendungsmethoden |
| AU719770B2 (en) * | 1995-11-23 | 2000-05-18 | Syngenta Participations Ag | Herbicidal composition |
| US7071146B1 (en) | 1996-11-11 | 2006-07-04 | Syngenta Crop Protection, Inc. | Herbicidal composition |
| AU7527898A (en) * | 1997-04-23 | 1998-11-13 | Novartis Ag | Herbicide |
| US5905057A (en) * | 1997-11-06 | 1999-05-18 | Rhone-Poulenc Agrochimie | Herbicidal 4-benzoylisoxazole-3-carboxylate liquid compositions comprising N-alkylpyrrolidinone stabilizer |
| US20040142198A1 (en) * | 2003-01-21 | 2004-07-22 | Thomas Hubert Van Steenkiste | Magnetostrictive/magnetic material for use in torque sensors |
| RU2242123C1 (ru) * | 2003-08-04 | 2004-12-20 | Кубанский государственный технологический университет | Средство для снижения токсического действия гербицида 2,4-дихлорфеноксиуксусной кислоты на подсолнечнике |
| CN101010323B (zh) | 2004-08-25 | 2010-06-16 | 埃科特莱茵药品有限公司 | 作为肾素抑制剂的双环壬烯衍生物 |
| RU2277329C1 (ru) * | 2005-02-07 | 2006-06-10 | Всероссийский научно-исследовательский институт биологической защиты растений | Способ защиты вегетирующих растений подсолнечника от повреждающего действия 2,4-д |
| RU2277332C1 (ru) * | 2005-02-09 | 2006-06-10 | Всероссийский научно-исследовательский институт биологической защиты растений | Способ защиты вегетирующих растений подсолнечника от повреждающего действия 2,4-д |
| RU2277333C1 (ru) * | 2005-02-14 | 2006-06-10 | Всероссийский научно-исследовательский институт биологической защиты растений | Способ защиты вегетирующих растений подсолнечника от повреждающего действия 2,4-д |
| RU2309571C1 (ru) * | 2006-05-02 | 2007-11-10 | Федеральное государственное образовательное учреждение высшего профессионального образования "Воронежский государственный аграрный университет имени К.Д. Глинки" (ФГОУ ВПО ВГАУ им. К.Д. Глинки) | Способ обогащения черноземной почвы при возделывании сельскохозяйственных культур |
| CN101069501A (zh) | 2007-05-28 | 2007-11-14 | 江苏龙灯化学有限公司 | 双取代长链烷基酰胺类作为结晶抑制剂在唑类农药液剂中的应用 |
| CN105732376A (zh) | 2007-08-16 | 2016-07-06 | 索尔维公司 | 制备4-氟取代的3-氧代-烷酸酯的方法 |
| CN102617560A (zh) * | 2011-01-30 | 2012-08-01 | 南京理工大学 | 呋喃解草唑的制备方法 |
| AR091901A1 (es) * | 2012-07-25 | 2015-03-11 | Amvac Chemical Corp | Composiciones herbicidas dispersables y metodos de uso de las mismas |
| CN106045861B (zh) * | 2016-05-26 | 2019-04-19 | 山东润博生物科技有限公司 | 一种连续化生产5-氟-2-硝基苯酚的方法及其系统 |
| CN107935858B (zh) * | 2016-10-12 | 2020-09-08 | 利尔化学股份有限公司 | 5-氟-2-硝基苯酚的制备方法 |
| MX2022015269A (es) | 2020-06-02 | 2023-01-11 | Bayer Ag | Herbicidas selectivos en base a carboxamidas de isoxazolina sustituidas y furilazol. |
| WO2024197109A1 (en) * | 2023-03-23 | 2024-09-26 | Fmc Corporation | Substituted oxazolidinones and imidazolinones as herbicides |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4072688A (en) * | 1975-02-14 | 1978-02-07 | Stauffer Chemical Company | Haloacyl and thiohaloacyl aryl-substituted oxazolidines and thiazolidines-herbicidal antidotes |
| BR7600775A (pt) * | 1975-02-14 | 1977-05-10 | Stauffer Chemical Co | Processo para a obtencao de(tio)haloacil-(tia)oxazolidinas arisubstituidas e composicoes herbicidas sinergeticas que as contem |
| CA1075701A (en) * | 1975-08-28 | 1980-04-15 | Harold M. Pitt | Production of n-substituted oxazolidines |
| US4400200A (en) * | 1977-10-11 | 1983-08-23 | Stauffer Chemical Company | Haloacyl and thiohaloacyl aryl-substituted oxazolidines and thiazolidines - herbicidal antidotes |
| GB1538318A (en) * | 1976-08-09 | 1979-01-17 | Stauffer Chemical Co | Preparation of n-substituted oxazolidines |
| US4219655A (en) * | 1979-07-16 | 1980-08-26 | Stauffer Chemical Company | Process for the production of N-acyl substituted oxazolidines |
| WO1981000406A1 (en) * | 1979-08-03 | 1981-02-19 | Stauffer Chemical Co | Spirooxazolidines and thiazolidines as herbicide antidotes |
| BR8205085A (pt) * | 1981-09-08 | 1983-08-09 | Stauffer Chemical Co | Composicao de antidoto herbicida e processo para estabelecer seletividade herbicida |
| US4648894A (en) * | 1983-05-20 | 1987-03-10 | Stauffer Chemical Co. | Herbicide compositions of extended soil life |
| PL144076B1 (en) * | 1983-08-24 | 1988-04-30 | Stauffer Chemical Co | Herbicide |
| US4613083A (en) * | 1984-06-21 | 1986-09-23 | Nordson Corporation | Adjustable powder spray gun |
| EP0190105A3 (de) * | 1985-01-31 | 1988-10-26 | Ciba-Geigy Ag | Herbizides Mittel |
| DE3600288A1 (de) * | 1986-01-08 | 1987-07-16 | Bayer Ag | Verwendung von amiden zur verbesserung der kulturpflanzen-vertraeglichkeit von herbizid wirksamen sulfonylharnstoff-derivaten |
| DE3618004A1 (de) * | 1986-05-28 | 1987-12-03 | Bayer Ag | Verwendung von amiden zur verbesserung der kulturpflanzen-vertraeglichkeit von herbizid wirksamen sulfonyliso(thio)-harnstoff-derivaten |
| NZ222993A (en) * | 1986-12-22 | 1989-09-27 | Stauffer Agricultural Chemical | Herbicidal compositions containing an acyl substituted oxazolidone antidote and two active herbicides |
-
1988
- 1988-07-01 US US07/212,621 patent/US5225570A/en not_active Expired - Lifetime
- 1988-08-12 HU HU884342A patent/HU205826B/hu unknown
- 1988-08-12 BG BG085225A patent/BG49813A3/xx unknown
- 1988-08-12 IL IL8742788A patent/IL87427A/en not_active IP Right Cessation
- 1988-08-12 RU SU884356197A patent/RU2093029C1/ru not_active IP Right Cessation
- 1988-08-12 DE DE8888870135T patent/DE3875556T2/de not_active Expired - Lifetime
- 1988-08-12 CN CN88104956A patent/CN1025141C/zh not_active Expired - Lifetime
- 1988-08-12 DK DK451988A patent/DK451988A/da not_active Application Discontinuation
- 1988-08-12 YU YU157188A patent/YU47061B/sh unknown
- 1988-08-12 ES ES88870135T patent/ES2010153T3/es not_active Expired - Lifetime
- 1988-08-12 JP JP63201816A patent/JPH0653737B2/ja not_active Expired - Fee Related
- 1988-08-12 EP EP88870135A patent/EP0304409B1/en not_active Expired - Lifetime
- 1988-08-12 PL PL27421788A patent/PL274217A1/xx unknown
- 1988-08-12 AU AU20660/88A patent/AU608639B2/en not_active Ceased
- 1988-08-12 CA CA000574701A patent/CA1328108C/en not_active Expired - Lifetime
- 1988-08-12 BR BR8804098A patent/BR8804098A/pt not_active IP Right Cessation
- 1988-08-12 UA UA4356197A patent/UA35539C2/uk unknown
-
1993
- 1993-01-21 GR GR930400123T patent/GR3006869T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US5225570A (en) | 1993-07-06 |
| BG49813A3 (en) | 1992-02-14 |
| EP0304409B1 (en) | 1992-10-28 |
| YU157188A (en) | 1990-08-31 |
| CA1328108C (en) | 1994-03-29 |
| DK451988D0 (da) | 1988-08-12 |
| AU608639B2 (en) | 1991-04-11 |
| HUT47789A (en) | 1989-04-28 |
| DE3875556D1 (de) | 1992-12-03 |
| JPS6483079A (en) | 1989-03-28 |
| HU205826B (en) | 1992-07-28 |
| DE3875556T2 (de) | 1993-05-06 |
| GR3006869T3 (en, 2012) | 1993-06-30 |
| BR8804098A (pt) | 1989-03-07 |
| EP0304409A1 (en) | 1989-02-22 |
| IL87427A0 (en) | 1989-01-31 |
| ES2010153T3 (es) | 1994-07-16 |
| ES2010153A4 (es) | 1989-11-01 |
| CN1031375A (zh) | 1989-03-01 |
| JPH0653737B2 (ja) | 1994-07-20 |
| YU47061B (sh) | 1994-12-28 |
| RU2093029C1 (ru) | 1997-10-20 |
| PL274217A1 (en) | 1989-04-17 |
| CN1025141C (zh) | 1994-06-29 |
| AU2066088A (en) | 1989-02-16 |
| DK451988A (da) | 1989-02-14 |
| UA35539C2 (uk) | 2001-04-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| MM9K | Patent not in force due to non-payment of renewal fees |