CH640108A5 - Unkrautvernichtungsmittel. - Google Patents
Unkrautvernichtungsmittel. Download PDFInfo
- Publication number
- CH640108A5 CH640108A5 CH133179A CH133179A CH640108A5 CH 640108 A5 CH640108 A5 CH 640108A5 CH 133179 A CH133179 A CH 133179A CH 133179 A CH133179 A CH 133179A CH 640108 A5 CH640108 A5 CH 640108A5
- Authority
- CH
- Switzerland
- Prior art keywords
- chloro
- methyl
- compounds
- triazine
- acetanilide
- Prior art date
Links
- 241000196324 Embryophyta Species 0.000 title claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 87
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 20
- -1 butylene, pentylene Chemical group 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 239000004009 herbicide Substances 0.000 claims description 13
- 238000009331 sowing Methods 0.000 claims description 11
- 229910052717 sulfur Chemical group 0.000 claims description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
- 239000004202 carbamide Substances 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 150000002431 hydrogen Chemical group 0.000 claims description 6
- 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 5
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 235000013877 carbamide Nutrition 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000011593 sulfur Chemical group 0.000 claims description 4
- VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical class ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 claims description 3
- 229960001413 acetanilide Drugs 0.000 claims description 3
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 claims description 3
- YTBYCJWEQNIZTM-UHFFFAOYSA-N 2-chloro-4,6-di(propan-2-yl)-2h-1,3,5-triazin-1-amine Chemical compound CC(C)C1=NC(Cl)N(N)C(C(C)C)=N1 YTBYCJWEQNIZTM-UHFFFAOYSA-N 0.000 claims description 2
- IYLMCARCSCXVNP-UHFFFAOYSA-N 2-chloro-n-(2,6-dimethylphenyl)-n-(propan-2-yloxymethyl)acetamide Chemical compound CC(C)OCN(C(=O)CCl)C1=C(C)C=CC=C1C IYLMCARCSCXVNP-UHFFFAOYSA-N 0.000 claims description 2
- ITUJTNVTYSHLGM-UHFFFAOYSA-N 2-methylsulfanyl-4,6-di(propan-2-yl)-2h-1,3,5-triazin-1-amine Chemical compound CSC1N=C(C(C)C)N=C(C(C)C)N1N ITUJTNVTYSHLGM-UHFFFAOYSA-N 0.000 claims description 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
- VTNQPKFIQCLBDU-UHFFFAOYSA-N Acetochlor Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1CC VTNQPKFIQCLBDU-UHFFFAOYSA-N 0.000 claims description 2
- DFDFCUAUFPAWMI-UHFFFAOYSA-N CCC1=C[S+](CC(C=C2)=CC=C2Cl)C(NC([O-])=O)=C1CC Chemical compound CCC1=C[S+](CC(C=C2)=CC=C2Cl)C(NC([O-])=O)=C1CC DFDFCUAUFPAWMI-UHFFFAOYSA-N 0.000 claims description 2
- RKECAJFMHWHHBI-UHFFFAOYSA-N CCCC1=C[S+](CCC)C(NC([O-])=O)=C1CCC Chemical compound CCCC1=C[S+](CCC)C(NC([O-])=O)=C1CCC RKECAJFMHWHHBI-UHFFFAOYSA-N 0.000 claims description 2
- RKKMJLZFJSRZBE-UHFFFAOYSA-N CC[S+]1C(NC([O-])=O)=C(CC(C)C)C(CC(C)C)=C1 Chemical compound CC[S+]1C(NC([O-])=O)=C(CC(C)C)C(CC(C)C)=C1 RKKMJLZFJSRZBE-UHFFFAOYSA-N 0.000 claims description 2
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 claims description 2
- HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 claims description 2
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 claims description 2
- 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 1
- UJANKJMOLOLHIH-UHFFFAOYSA-N C(CCC)C1=NC(=NC(=N1)N(CC)N)Cl Chemical compound C(CCC)C1=NC(=NC(=N1)N(CC)N)Cl UJANKJMOLOLHIH-UHFFFAOYSA-N 0.000 claims 1
- APRNCHGYBXRIIX-UHFFFAOYSA-N CC[S+]1C(NC([O-])=O)=C(CCC2CCCCC2)C=C1 Chemical compound CC[S+]1C(NC([O-])=O)=C(CCC2CCCCC2)C=C1 APRNCHGYBXRIIX-UHFFFAOYSA-N 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 claims 1
- BCQMBFHBDZVHKU-UHFFFAOYSA-N terbumeton Chemical compound CCNC1=NC(NC(C)(C)C)=NC(OC)=N1 BCQMBFHBDZVHKU-UHFFFAOYSA-N 0.000 claims 1
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 claims 1
- 150000003918 triazines Chemical class 0.000 claims 1
- 150000003672 ureas Chemical class 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 239000004480 active ingredient Substances 0.000 description 24
- 230000002363 herbicidal effect Effects 0.000 description 24
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 230000000254 damaging effect Effects 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000000729 antidote Substances 0.000 description 13
- 239000000460 chlorine Substances 0.000 description 12
- 229910052801 chlorine Inorganic materials 0.000 description 12
- GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- YRMLFORXOOIJDR-UHFFFAOYSA-N Dichlormid Chemical compound ClC(Cl)C(=O)N(CC=C)CC=C YRMLFORXOOIJDR-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 231100000674 Phytotoxicity Toxicity 0.000 description 8
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000013543 active substance Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 230000009931 harmful effect Effects 0.000 description 7
- 238000002329 infrared spectrum Methods 0.000 description 7
- RDEKOGBRLXGCAK-UHFFFAOYSA-N 2,2-dichloro-1-(1-thia-4-azaspiro[4.5]decan-4-yl)ethanone Chemical compound ClC(Cl)C(=O)N1CCSC11CCCCC1 RDEKOGBRLXGCAK-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 244000038559 crop plants Species 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 150000001728 carbonyl compounds Chemical class 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 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 5
- 230000000885 phytotoxic effect Effects 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 235000003222 Helianthus annuus Nutrition 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000004495 emulsifiable concentrate Substances 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000010933 acylation Effects 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 239000007900 aqueous suspension Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- WCGGWVOVFQNRRS-UHFFFAOYSA-N dichloroacetamide Chemical class NC(=O)C(Cl)Cl WCGGWVOVFQNRRS-UHFFFAOYSA-N 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- QWWHRELOCZEQNZ-UHFFFAOYSA-N 2,2-dichloro-1-(1-oxa-4-azaspiro[4.5]decan-4-yl)ethanone Chemical compound ClC(Cl)C(=O)N1CCOC11CCCCC1 QWWHRELOCZEQNZ-UHFFFAOYSA-N 0.000 description 2
- YHAOXSWOQSRJQE-UHFFFAOYSA-N 2,2-dichloro-1-(1-oxa-5-azaspiro[5.5]undecan-5-yl)ethanone Chemical compound ClC(Cl)C(=O)N1CCCOC11CCCCC1 YHAOXSWOQSRJQE-UHFFFAOYSA-N 0.000 description 2
- VIKUZSGMOLEKIH-UHFFFAOYSA-N 2,2-dichloro-1-(1-oxo-1$l^{4}-thia-4-azaspiro[4.5]decan-4-yl)ethanone Chemical compound ClC(Cl)C(=O)N1CCS(=O)C11CCCCC1 VIKUZSGMOLEKIH-UHFFFAOYSA-N 0.000 description 2
- ARFFVYSBJQFUBV-UHFFFAOYSA-N 2,2-dichloro-1-(1-thia-4-azaspiro[4.4]nonan-4-yl)ethanone Chemical compound ClC(Cl)C(=O)N1CCSC11CCCC1 ARFFVYSBJQFUBV-UHFFFAOYSA-N 0.000 description 2
- KGWNRZLPXLBMPS-UHFFFAOYSA-N 2h-1,3-oxazine Chemical compound C1OC=CC=N1 KGWNRZLPXLBMPS-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 244000062793 Sorghum vulgare Species 0.000 description 2
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- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
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- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 1
- ANYJHCKEXQAPBZ-UHFFFAOYSA-N 2,2-dichloro-1-(1-oxa-4-azaspiro[4.6]undecan-4-yl)ethanone Chemical compound ClC(Cl)C(=O)N1CCOC11CCCCCC1 ANYJHCKEXQAPBZ-UHFFFAOYSA-N 0.000 description 1
- QPDLPGADMYGJIB-UHFFFAOYSA-N 2,2-dichloro-1-(1-oxa-5-azaspiro[5.6]dodecan-5-yl)ethanone Chemical compound ClC(Cl)C(=O)N1CCCOC11CCCCCC1 QPDLPGADMYGJIB-UHFFFAOYSA-N 0.000 description 1
- MOHVRUZXQQMGLP-UHFFFAOYSA-N 2,2-dichloro-1-(1-thia-4-azaspiro[4.6]undecan-4-yl)ethanone Chemical compound ClC(Cl)C(=O)N1CCSC11CCCCCC1 MOHVRUZXQQMGLP-UHFFFAOYSA-N 0.000 description 1
- JHWJSQBVSGWRFG-UHFFFAOYSA-N 2,2-dichloro-1-(6-oxa-10-azaspiro[4.5]decan-10-yl)ethanone Chemical compound ClC(Cl)C(=O)N1CCCOC11CCCC1 JHWJSQBVSGWRFG-UHFFFAOYSA-N 0.000 description 1
- YVXOLHCUUFEQFQ-UHFFFAOYSA-N 2,2-dichloro-1-(8-methyl-1-oxa-4-azaspiro[4.5]decan-4-yl)ethanone Chemical compound C1CC(C)CCC21N(C(=O)C(Cl)Cl)CCO2 YVXOLHCUUFEQFQ-UHFFFAOYSA-N 0.000 description 1
- VPLYDVNPBIXMHB-UHFFFAOYSA-N 2-n-butyl-6-chloro-4-n-ethyl-1,3,5-triazine-2,4-diamine Chemical compound CCCCNC1=NC(Cl)=NC(NCC)=N1 VPLYDVNPBIXMHB-UHFFFAOYSA-N 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- OOHIAOSLOGDBCE-UHFFFAOYSA-N 6-chloro-4-n-cyclopropyl-2-n-propan-2-yl-1,3,5-triazine-2,4-diamine Chemical compound CC(C)NC1=NC(Cl)=NC(NC2CC2)=N1 OOHIAOSLOGDBCE-UHFFFAOYSA-N 0.000 description 1
- MDBGGTQNNUOQRC-UHFFFAOYSA-N Allidochlor Chemical compound ClCC(=O)N(CC=C)CC=C MDBGGTQNNUOQRC-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- DFCAFRGABIXSDS-UHFFFAOYSA-N Cycloate Chemical compound CCSC(=O)N(CC)C1CCCCC1 DFCAFRGABIXSDS-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229940075522 antidotes Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229940058963 dichloroacetamide derivative drug for amoebiasis and other protozoal diseases Drugs 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 150000007529 inorganic bases Chemical class 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
- 239000000463 material Substances 0.000 description 1
- MQWCXKGKQLNYQG-UHFFFAOYSA-N methyl cyclohexan-4-ol Natural products CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 1
- HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- LIXFJRLISFERDN-UHFFFAOYSA-N o-ethyl n,n-dipropylcarbamothioate Chemical compound CCCN(CCC)C(=S)OCC LIXFJRLISFERDN-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical class OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 239000004476 plant protection product Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 235000020238 sunflower seed Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- 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
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/04—1,3-Thiazines; Hydrogenated 1,3-thiazines
- C07D279/06—1,3-Thiazines; Hydrogenated 1,3-thiazines not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/04—1,3-Thiazines; Hydrogenated 1,3-thiazines
- C07D279/08—1,3-Thiazines; Hydrogenated 1,3-thiazines condensed with carbocyclic rings or ring systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Toxicology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUME002142 HU178301B (en) | 1978-02-06 | 1978-02-06 | Herbicide compositions containing naphthaline-carboxylic acid derivatives as antidotes and carbamide derivatives and antidote compositions containing naphthaline-carboxylic acid derivatives |
| BE193625A BE874361A (fr) | 1978-02-06 | 1979-02-22 | Composition herbicide selective |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH640108A5 true CH640108A5 (de) | 1983-12-30 |
Family
ID=25651298
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH133179A CH640108A5 (de) | 1978-02-06 | 1979-02-12 | Unkrautvernichtungsmittel. |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4256481A (en, 2012) |
| CH (1) | CH640108A5 (en, 2012) |
| DE (1) | DE2905650A1 (en, 2012) |
| FR (1) | FR2448857B1 (en, 2012) |
| GB (1) | GB2043447B (en, 2012) |
| LU (1) | LU80912A1 (en, 2012) |
| NL (1) | NL187256C (en, 2012) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5011526A (en) * | 1978-09-20 | 1991-04-30 | Ici Americas Inc. | Herbicide compositions of extended soil life |
| HU187284B (en) * | 1980-12-11 | 1985-12-28 | Mta Koezponti Kemiai Kutato In | Herbicide compositions containing antitoxines of aldehyde- and ketone-derivatives |
| CA1196917A (en) * | 1982-03-26 | 1985-11-19 | Derek A. Wood | N-substituted-tetrahydrothiazines, process for their preparation, and their use as pesticides |
| DE3403147A1 (de) * | 1984-01-31 | 1985-08-01 | Wella Ag, 6100 Darmstadt | 3-carbamoyl- und 3-thiocarbamoyl-tetrahydro-1,3-thiazin-2-thione, verfahren zu ihrer herstellung sowie diese verbindungen enthaltende hautbehandlungsmittel |
| US5051125A (en) * | 1986-03-04 | 1991-09-24 | Ici Americas Inc. | Synergistic herbicidal composition of cycloate and cyanazine |
| US4938796A (en) * | 1987-07-06 | 1990-07-03 | Ici Americas Inc. | Herbicidal compositions of acylated 1,3-dicarbonyl herbicides and antidotes therefor |
| HU210367B (en) * | 1989-04-11 | 1995-04-28 | Nitrokemia Ipartelepek | Antidoted herbicidal compositions and antidotal composition and process for their use |
| US5527762A (en) * | 1990-12-12 | 1996-06-18 | Zeneca Limited | Antidoting herbicidal 3-isoxazolidinone compounds |
| 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 |
| 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 |
| FR2762475B1 (fr) * | 1997-04-25 | 1999-07-16 | Nitrokemia Rt | Compositions herbicides a base de chloroacetamide et de 1,3,5-triazine et leur utilisation |
| JP3967431B2 (ja) * | 1997-09-03 | 2007-08-29 | 株式会社トクヤマ | エテニルアミド系除草剤組成物 |
| CN116283812A (zh) * | 2023-03-04 | 2023-06-23 | 徐州彰梁生化科技有限公司 | 一种苯叉酰胺生产工艺 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2035796A1 (de) * | 1970-07-18 | 1972-01-27 | Bayer Ag | Verfahren zum Austausch von N Nitroso |
| CA1174865A (en) * | 1971-04-16 | 1984-09-25 | Ferenc M. Pallos | Thiolcarbamate herbicides containing nitrogen containing antidote |
| US3989503A (en) * | 1972-10-13 | 1976-11-02 | Stauffer Chemical Company | Herbicidal antidote compositions with substituted oxazolidines and thiazolidines |
| HU165736B (en, 2012) * | 1972-04-13 | 1974-10-28 | ||
| US3859292A (en) * | 1972-08-15 | 1975-01-07 | Scm Corp | N-haloacyl (2-spirocycloaliphatic) oxazolidines |
| GB1420685A (en) * | 1972-08-15 | 1976-01-07 | Scm Corp | Substituted oxazolidines |
| US3881908A (en) * | 1972-08-15 | 1975-05-06 | Scm Corp | Herbicidal N-haloacyl (2-spirocycloaliphatic) oxazolidines |
| US3884671A (en) * | 1972-08-15 | 1975-05-20 | Scm Corp | Herbicidal n-haloacyl (2-alkylated) oxazolidines |
| GB1457128A (en) * | 1972-10-13 | 1976-12-01 | Stauffer Chemical Co | Substituted oxazolidines and thiazolidines |
| CH574207A5 (en, 2012) * | 1973-01-25 | 1976-04-15 | Ciba Geigy Ag | |
| US4124372A (en) * | 1973-05-02 | 1978-11-07 | Stauffer Chemical Company | Herbicidal antidote compositions with substituted oxazolidines and thiazolidines |
| GB1403876A (en) * | 1973-05-04 | 1975-08-28 | Stauffer Chemical Co | Thiazolidine derivatives and their use as herbicide 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 |
| FR2310348A1 (fr) * | 1975-05-07 | 1976-12-03 | Ugine Kuhlmann | Nouveaux derives heterocycliques antidotes contre herbicides |
| HU178064B (en) * | 1978-05-31 | 1982-02-28 | Noevenyvedelmi Kutato Intezet | Antidote composition containing n-/trimethyl-cyclopentillidene /-ethanol-amine-dichloracetate and process for preparing the active material |
-
1979
- 1979-02-12 CH CH133179A patent/CH640108A5/de not_active IP Right Cessation
- 1979-02-12 LU LU80912A patent/LU80912A1/de unknown
- 1979-02-14 GB GB7905299A patent/GB2043447B/en not_active Expired
- 1979-02-14 DE DE19792905650 patent/DE2905650A1/de active Granted
- 1979-02-19 FR FR7904130A patent/FR2448857B1/fr not_active Expired
- 1979-02-27 NL NLAANVRAGE7901548,A patent/NL187256C/xx not_active IP Right Cessation
- 1979-03-02 US US06/017,034 patent/US4256481A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| GB2043447A (en) | 1980-10-08 |
| DE2905650A1 (de) | 1980-08-21 |
| NL187256C (nl) | 1991-08-01 |
| NL7901548A (nl) | 1980-08-29 |
| FR2448857B1 (fr) | 1982-05-28 |
| US4256481A (en) | 1981-03-17 |
| GB2043447B (en) | 1983-10-26 |
| LU80912A1 (de) | 1979-06-07 |
| FR2448857A1 (fr) | 1980-09-12 |
| DE2905650C2 (en, 2012) | 1989-02-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |