PL110714B1 - Method of producing new heterocyclic derivatives containing in ring nitrogen,specially oxazolidine or thiazolidine - Google Patents
Method of producing new heterocyclic derivatives containing in ring nitrogen,specially oxazolidine or thiazolidine Download PDFInfo
- Publication number
- PL110714B1 PL110714B1 PL1976189381A PL18938176A PL110714B1 PL 110714 B1 PL110714 B1 PL 110714B1 PL 1976189381 A PL1976189381 A PL 1976189381A PL 18938176 A PL18938176 A PL 18938176A PL 110714 B1 PL110714 B1 PL 110714B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- group
- alkyl
- compound
- oxazolidine
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 title claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 title claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 title claims description 4
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 title claims description 3
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 49
- 238000006243 chemical reaction Methods 0.000 claims description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 16
- -1 chloro-aryl Chemical group 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 12
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 125000001188 haloalkyl group Chemical group 0.000 claims description 9
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 150000008065 acid anhydrides Chemical class 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 5
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 3
- 150000007529 inorganic bases Chemical class 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- MPKBJDUMKUXTGV-UHFFFAOYSA-N ClC(C1OCCN1C(C)=O)(Cl)Cl Chemical compound ClC(C1OCCN1C(C)=O)(Cl)Cl MPKBJDUMKUXTGV-UHFFFAOYSA-N 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 125000004965 chloroalkyl group Chemical group 0.000 claims description 2
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 2
- 150000003462 sulfoxides Chemical class 0.000 claims description 2
- 239000004009 herbicide Substances 0.000 description 57
- 239000000729 antidote Substances 0.000 description 49
- 230000002363 herbicidal effect Effects 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- 241000196324 Embryophyta Species 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 240000008042 Zea mays Species 0.000 description 21
- 239000000243 solution Substances 0.000 description 19
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 18
- GUVLYNGULCJVDO-UHFFFAOYSA-N EPTC Chemical compound CCCN(CCC)C(=O)SCC GUVLYNGULCJVDO-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 14
- 235000009973 maize Nutrition 0.000 description 14
- 235000013339 cereals Nutrition 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- 239000012074 organic phase Substances 0.000 description 12
- 238000001953 recrystallisation Methods 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 239000013068 control sample Substances 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 239000002689 soil Substances 0.000 description 10
- 238000011282 treatment Methods 0.000 description 10
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 229940075522 antidotes Drugs 0.000 description 8
- 238000000921 elemental analysis Methods 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- 241000209219 Hordeum Species 0.000 description 7
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 235000007340 Hordeum vulgare Nutrition 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000009331 sowing Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000010908 decantation Methods 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 239000003815 herbicide antidote Substances 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- VQCSISBLWARLJL-UHFFFAOYSA-N 2-(trichloromethyl)-1,3-thiazolidine Chemical compound ClC(Cl)(Cl)C1NCCS1 VQCSISBLWARLJL-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 4
- MCOQHIWZJUDQIC-UHFFFAOYSA-N barban Chemical compound ClCC#CCOC(=O)NC1=CC=CC(Cl)=C1 MCOQHIWZJUDQIC-UHFFFAOYSA-N 0.000 description 4
- 235000005822 corn Nutrition 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- JVTFIEPMJSJBMH-UHFFFAOYSA-N 2,2-dichloro-1-[2-(trichloromethyl)-1,3-thiazolidin-3-yl]ethanone Chemical compound ClC(Cl)C(=O)N1CCSC1C(Cl)(Cl)Cl JVTFIEPMJSJBMH-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 241000219198 Brassica Species 0.000 description 3
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 3
- RQHMQURGSQBBJY-UHFFFAOYSA-N (2,2-dichloroacetyl) 2,2-dichloroacetate Chemical compound ClC(Cl)C(=O)OC(=O)C(Cl)Cl RQHMQURGSQBBJY-UHFFFAOYSA-N 0.000 description 2
- SHXGGYLLZCCNAX-UHFFFAOYSA-N (3-chlorophenyl) carbamate Chemical compound NC(=O)OC1=CC=CC(Cl)=C1 SHXGGYLLZCCNAX-UHFFFAOYSA-N 0.000 description 2
- KGUDNHCITIQTPD-UHFFFAOYSA-N 2,2-dichloro-1-[2-(dichloromethyl)-1,3-oxazolidin-3-yl]ethanone Chemical compound ClC(Cl)C1OCCN1C(=O)C(Cl)Cl KGUDNHCITIQTPD-UHFFFAOYSA-N 0.000 description 2
- PHDMPTTZAVGJKN-UHFFFAOYSA-N 2-(tribromomethyl)-1,3-oxazolidine Chemical compound BrC(Br)(Br)C1NCCO1 PHDMPTTZAVGJKN-UHFFFAOYSA-N 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical class ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 description 2
- 241001057636 Dracaena deremensis Species 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 244000020551 Helianthus annuus Species 0.000 description 2
- 235000003222 Helianthus annuus Nutrition 0.000 description 2
- 239000005573 Linuron Substances 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000007689 inspection Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- HHBOUFYYHJJTNU-UHFFFAOYSA-N 1,3,6-thiadiazepane-2,7-dithione Chemical compound S=C1NCCNC(=S)S1 HHBOUFYYHJJTNU-UHFFFAOYSA-N 0.000 description 1
- UCCSPJPIAZEQQQ-UHFFFAOYSA-N 1-(1,3-thiazolidin-2-yl)ethanone Chemical compound CC(=O)C1NCCS1 UCCSPJPIAZEQQQ-UHFFFAOYSA-N 0.000 description 1
- UGIOPQPNNHGOOT-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-1-(methoxymethyl)urea Chemical compound COCN(C(N)=O)C1=CC=C(Cl)C(Cl)=C1 UGIOPQPNNHGOOT-UHFFFAOYSA-N 0.000 description 1
- ZEEUECJNGDPJMC-UHFFFAOYSA-N 1-[2-(trichloromethyl)-1,3-oxazolidin-3-yl]pentan-1-one Chemical compound CCCCC(=O)N1CCOC1C(Cl)(Cl)Cl ZEEUECJNGDPJMC-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- NOLWAGXBBKJFEE-UHFFFAOYSA-N 1-aminosulfanylethanol Chemical compound CC(O)SN NOLWAGXBBKJFEE-UHFFFAOYSA-N 0.000 description 1
- YTGSYRVSBPFKMQ-UHFFFAOYSA-N 2,2,2-tribromoacetaldehyde Chemical compound BrC(Br)(Br)C=O YTGSYRVSBPFKMQ-UHFFFAOYSA-N 0.000 description 1
- SOAQZWBTFXPSKD-UHFFFAOYSA-N 2,2-dichloro-1-[1-oxo-2-(trichloromethyl)-1,3-thiazolidin-3-yl]ethanone Chemical compound ClC(Cl)C(=O)N1CCS(=O)C1C(Cl)(Cl)Cl SOAQZWBTFXPSKD-UHFFFAOYSA-N 0.000 description 1
- JNDQCLSCEIPXMN-UHFFFAOYSA-N 2,2-dichloro-1-[2-(tribromomethyl)-1,3-oxazolidin-3-yl]ethanone Chemical compound ClC(Cl)C(=O)N1CCOC1C(Br)(Br)Br JNDQCLSCEIPXMN-UHFFFAOYSA-N 0.000 description 1
- BLAJBHZIAJCKOI-UHFFFAOYSA-N 2,2-dichloro-1-[2-(trichloromethyl)-2h-1,3-benzoxazol-3-yl]ethanone Chemical compound C1=CC=C2N(C(=O)C(Cl)Cl)C(C(Cl)(Cl)Cl)OC2=C1 BLAJBHZIAJCKOI-UHFFFAOYSA-N 0.000 description 1
- GOBAVXNNRYZFQH-UHFFFAOYSA-N 2,2-dichloro-1-[4,4-dimethyl-2-(trichloromethyl)-1,3-oxazolidin-3-yl]ethanone Chemical compound CC1(C)COC(C(Cl)(Cl)Cl)N1C(=O)C(Cl)Cl GOBAVXNNRYZFQH-UHFFFAOYSA-N 0.000 description 1
- HDXWIGWJPABRKG-UHFFFAOYSA-N 2,2-dichloro-1-[4-ethyl-2-(trichloromethyl)-1,3-oxazolidin-3-yl]ethanone Chemical compound CCC1COC(C(Cl)(Cl)Cl)N1C(=O)C(Cl)Cl HDXWIGWJPABRKG-UHFFFAOYSA-N 0.000 description 1
- MKDVVYSFCOAWPD-UHFFFAOYSA-N 2-(dichloromethyl)-1,3-oxazolidine Chemical compound ClC(Cl)C1NCCO1 MKDVVYSFCOAWPD-UHFFFAOYSA-N 0.000 description 1
- YFZMDNJBQWEQRG-UHFFFAOYSA-N 2-(trichloromethyl)-1,3-oxazolidine Chemical compound ClC(Cl)(Cl)C1NCCO1 YFZMDNJBQWEQRG-UHFFFAOYSA-N 0.000 description 1
- VKPHHYUEMRNFSX-UHFFFAOYSA-N 2-aminobutan-2-ol Chemical compound CCC(C)(N)O VKPHHYUEMRNFSX-UHFFFAOYSA-N 0.000 description 1
- GPBICYITRWEKAX-UHFFFAOYSA-N 2-aminosulfanylethanol Chemical compound NSCCO GPBICYITRWEKAX-UHFFFAOYSA-N 0.000 description 1
- SJSXTEXASMKMCW-UHFFFAOYSA-N 2-chloro-N-(2,6-diethyl-3-methylphenyl)-N-methoxyacetamide Chemical compound CON(C1=C(C(=CC=C1CC)C)CC)C(CCl)=O SJSXTEXASMKMCW-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- ZJAFQAPHWPSKRZ-UHFFFAOYSA-N 4-nitrobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=C([N+]([O-])=O)C=C1 ZJAFQAPHWPSKRZ-UHFFFAOYSA-N 0.000 description 1
- OTLNPYWUJOZPPA-UHFFFAOYSA-N 4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-N 0.000 description 1
- YNIFAXORHVZTGQ-UHFFFAOYSA-N 5-methyl-2-(trichloromethyl)-1,3-oxazolidine Chemical compound CC1CNC(C(Cl)(Cl)Cl)O1 YNIFAXORHVZTGQ-UHFFFAOYSA-N 0.000 description 1
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 description 1
- 235000021537 Beetroot Nutrition 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- KAEBAIRMQCPGGU-UHFFFAOYSA-N ClCC1OCCN1 Chemical compound ClCC1OCCN1 KAEBAIRMQCPGGU-UHFFFAOYSA-N 0.000 description 1
- DFCAFRGABIXSDS-UHFFFAOYSA-N Cycloate Chemical compound CCSC(=O)N(CC)C1CCCCC1 DFCAFRGABIXSDS-UHFFFAOYSA-N 0.000 description 1
- SPANOECCGNXGNR-UITAMQMPSA-N Diallat Chemical compound CC(C)N(C(C)C)C(=O)SC\C(Cl)=C\Cl SPANOECCGNXGNR-UITAMQMPSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- WARIWGPBHKPYON-UHFFFAOYSA-N Ethiolate Chemical compound CCSC(=O)N(CC)CC WARIWGPBHKPYON-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- ZKGWPJYSXASUHL-UHFFFAOYSA-N N-chloro-N-propan-2-ylaniline Chemical compound ClN(C(C)C)C1=CC=CC=C1 ZKGWPJYSXASUHL-UHFFFAOYSA-N 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 229910019950 S—O Inorganic materials 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- BJNXJPYKYOKYOR-UHFFFAOYSA-N [C].ClC(Cl)Cl Chemical compound [C].ClC(Cl)Cl BJNXJPYKYOKYOR-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 1
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001804 chlorine Chemical class 0.000 description 1
- JXCGFZXSOMJFOA-UHFFFAOYSA-N chlorotoluron Chemical compound CN(C)C(=O)NC1=CC=C(C)C(Cl)=C1 JXCGFZXSOMJFOA-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- DLLJVQNYBYOKGS-UHFFFAOYSA-N ethoxyethane;pentane Chemical compound CCCCC.CCOCC DLLJVQNYBYOKGS-UHFFFAOYSA-N 0.000 description 1
- XYSNXNHHBUFLLV-UHFFFAOYSA-N ethyl n-(3-methylphenyl)carbamate Chemical compound CCOC(=O)NC1=CC=CC(C)=C1 XYSNXNHHBUFLLV-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 125000005347 halocycloalkyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000012764 mineral filler Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002917 oxazolidines Chemical class 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- JKWONDKDFCXETQ-UHFFFAOYSA-N propan-2-ylcarbamothioic s-acid Chemical compound CC(C)NC(S)=O JKWONDKDFCXETQ-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- PUNUCLJJWUUKFB-UHFFFAOYSA-N s-ethyl n-cyclohexylcarbamothioate Chemical compound CCSC(=O)NC1CCCCC1 PUNUCLJJWUUKFB-UHFFFAOYSA-N 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003548 thiazolidines Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000004563 wettable powder Substances 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- 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
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/06—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
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 |
|---|---|---|---|
| FR7514297A FR2310348A1 (fr) | 1975-05-07 | 1975-05-07 | Nouveaux derives heterocycliques antidotes contre herbicides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL110714B1 true PL110714B1 (en) | 1980-07-31 |
Family
ID=9154965
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1976189381A PL110714B1 (en) | 1975-05-07 | 1976-05-07 | Method of producing new heterocyclic derivatives containing in ring nitrogen,specially oxazolidine or thiazolidine |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4197110A (h) |
| BE (1) | BE841320A (h) |
| BG (2) | BG27370A3 (h) |
| BR (1) | BR7602846A (h) |
| CA (1) | CA1087183A (h) |
| CH (1) | CH612187A5 (h) |
| CS (1) | CS189768B2 (h) |
| DD (2) | DD132291A5 (h) |
| DE (1) | DE2620101A1 (h) |
| DK (1) | DK204976A (h) |
| FR (1) | FR2310348A1 (h) |
| GB (1) | GB1544679A (h) |
| IE (1) | IE43133B1 (h) |
| IL (1) | IL49515A (h) |
| IT (1) | IT1070224B (h) |
| LU (1) | LU74883A1 (h) |
| NL (1) | NL7604764A (h) |
| PL (1) | PL110714B1 (h) |
| PT (1) | PT65075B (h) |
| RO (1) | RO68892A (h) |
| SU (1) | SU759045A3 (h) |
| YU (1) | YU108076A (h) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0002206A1 (de) * | 1977-11-24 | 1979-06-13 | Ciba-Geigy Ag | Halogenierte Buttersäurechloride, Verfahren zu deren Herstellung und ihre Verwendung als Zwischenprodukte zur Herstellung von Schädlingsbekämpfungsmitteln |
| LU80912A1 (de) * | 1978-02-06 | 1979-06-07 | Nitrokemia Ipartelepek | Unkrautvernichtungsmittel |
| US4437875A (en) | 1980-04-14 | 1984-03-20 | Monsanto Company | 2,4-Disubstituted-5-thiazole-carboxylic acids and derivatives |
| US4602454A (en) * | 1978-05-15 | 1986-07-29 | Monsanto Company | 2,4-disubstituted-5-thiazole-carboxylic acids and derivatives |
| US4199506A (en) * | 1978-05-15 | 1980-04-22 | Monsanto Company | 2,4-Disubstituted-5-thiazolecarboxylic acids and derivatives |
| US4602937A (en) * | 1978-05-15 | 1986-07-29 | Monsanto Company | 2,4-Disubstituted-5-thiazole-carboxylic acids and derivatives |
| US4437876A (en) | 1980-04-14 | 1984-03-20 | Monsanto Company | 2,4-Disubstituted-5-thiazole-carboxylic acids and derivatives |
| DE2828293A1 (de) * | 1978-06-28 | 1980-01-10 | Bayer Ag | N-dichloracetyl-1,2,3,4-tetrahydro- chinaldin, verfahren zu dessen herstellung und dessen verwendung zur verhuetung von herbizidschaeden an kulturpflanzen |
| DE2832974A1 (de) * | 1978-07-27 | 1980-02-14 | Basf Ag | Ein thiolcarbamat enthaltende herbizide mittel |
| GR66644B (h) * | 1978-07-27 | 1981-04-03 | Basf Ag | |
| DE2948535A1 (de) * | 1979-12-03 | 1981-06-25 | Basf Ag, 6700 Ludwigshafen | Dichloracetamide, herbizide mittel, die acetanilide als herbizide wirkstoffe und diese dichloracetamide als antagonistische mittel enthalten, sowie ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses |
| HU187284B (en) * | 1980-12-11 | 1985-12-28 | Mta Koezponti Kemiai Kutato In | Herbicide compositions containing antitoxines of aldehyde- and ketone-derivatives |
| US4586948A (en) * | 1981-04-22 | 1986-05-06 | Monsanto Company | 2,4-disubstituted-5-thiazole-carboxylic acids and derivatives |
| IT1194793B (it) * | 1981-05-12 | 1988-09-28 | Corvi Camillo Spa | Derivati tiazolidinici ad attivita' farmacologica,procedimento per la loro preparazione e composizioni farmaceutiche contenenti detti derivati |
| DE3120859A1 (de) * | 1981-05-26 | 1982-12-23 | Basf Ag, 6700 Ludwigshafen | Dihalogenacetamide, verfahren zu ihrer herstellung und herbizide mittel, die acetanilide als herbizide wirkstoffe und diese dihalogenacetamide als antagonistische mittel enthalten |
| MX159669A (es) * | 1983-12-12 | 1989-08-02 | Ciba Geigy Ag | Procedimiento para la preparacion de derivados de acilamida |
| US5256625A (en) * | 1987-08-13 | 1993-10-26 | Monsanto Company | Safening imidazolinone herbicides |
| US4824468A (en) * | 1987-10-13 | 1989-04-25 | Ici Americas Inc. | Herbicidal oxazolidines and methods of use |
| US5773455A (en) * | 1996-06-28 | 1998-06-30 | Biomeasure, Incorporated | Inhibitors of prenyl transferases |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3707541A (en) * | 1970-03-16 | 1972-12-26 | Johnson & Son Inc S C | Oxazolidine and tetrahydrooxazine compounds having insect repellent activity |
| US3825555A (en) * | 1970-03-16 | 1974-07-23 | Johnson & Son Inc S C | 3-substituted 4-alkanoyl oxazaspiro insect repellents |
| US3859252A (en) * | 1972-04-28 | 1975-01-07 | Uniroyal Inc | Polyamido polysulfone thermoplastics and intermediates thereof |
| US3859292A (en) * | 1972-08-15 | 1975-01-07 | Scm Corp | N-haloacyl (2-spirocycloaliphatic) oxazolidines |
| US3884671A (en) * | 1972-08-15 | 1975-05-20 | Scm Corp | Herbicidal n-haloacyl (2-alkylated) oxazolidines |
| US4124372A (en) * | 1973-05-02 | 1978-11-07 | Stauffer Chemical Company | Herbicidal antidote compositions with substituted oxazolidines and thiazolidines |
| US3959304A (en) * | 1974-07-01 | 1976-05-25 | Stauffer Chemical Company | Certain 3-haloacyl-2,2,5-trimethyl-oxazolidines |
-
1975
- 1975-05-07 FR FR7514297A patent/FR2310348A1/fr active Granted
-
1976
- 1976-04-29 YU YU01080/76A patent/YU108076A/xx unknown
- 1976-04-30 BE BE1007352A patent/BE841320A/xx unknown
- 1976-05-03 BG BG033087A patent/BG27370A3/xx unknown
- 1976-05-03 IL IL49515A patent/IL49515A/xx unknown
- 1976-05-03 BG BG034110A patent/BG27526A4/xx unknown
- 1976-05-05 CH CH566176A patent/CH612187A5/xx not_active IP Right Cessation
- 1976-05-05 NL NL7604764A patent/NL7604764A/xx not_active Application Discontinuation
- 1976-05-05 US US05/683,599 patent/US4197110A/en not_active Expired - Lifetime
- 1976-05-05 LU LU74883A patent/LU74883A1/xx unknown
- 1976-05-06 DE DE19762620101 patent/DE2620101A1/de not_active Withdrawn
- 1976-05-06 GB GB18520/76A patent/GB1544679A/en not_active Expired
- 1976-05-06 RO RO7686027A patent/RO68892A/ro unknown
- 1976-05-06 PT PT65075A patent/PT65075B/pt unknown
- 1976-05-06 CA CA251,926A patent/CA1087183A/fr not_active Expired
- 1976-05-06 BR BR2846/76A patent/BR7602846A/pt unknown
- 1976-05-06 CS CS763031A patent/CS189768B2/cs unknown
- 1976-05-07 IE IE987/76A patent/IE43133B1/en unknown
- 1976-05-07 IT IT68121/76A patent/IT1070224B/it active
- 1976-05-07 PL PL1976189381A patent/PL110714B1/pl unknown
- 1976-05-07 DD DD7600201853A patent/DD132291A5/xx unknown
- 1976-05-07 DK DK204976A patent/DK204976A/da unknown
- 1976-05-07 DD DD7600192728A patent/DD127928A5/xx unknown
- 1976-08-04 SU SU762387471A patent/SU759045A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| US4197110A (en) | 1980-04-08 |
| SU759045A3 (ru) | 1980-08-23 |
| PT65075A (fr) | 1976-06-01 |
| IE43133B1 (en) | 1980-12-31 |
| GB1544679A (en) | 1979-04-25 |
| YU108076A (en) | 1982-06-30 |
| BG27526A4 (en) | 1979-11-12 |
| FR2310348B1 (h) | 1978-06-09 |
| IT1070224B (it) | 1985-03-29 |
| RO68892A (ro) | 1982-09-09 |
| FR2310348A1 (fr) | 1976-12-03 |
| CH612187A5 (h) | 1979-07-13 |
| DK204976A (da) | 1976-11-08 |
| DD132291A5 (de) | 1978-09-20 |
| BG27370A3 (en) | 1979-10-12 |
| PT65075B (fr) | 1977-09-13 |
| CS189768B2 (en) | 1979-04-30 |
| DD127928A5 (de) | 1977-10-19 |
| IL49515A0 (en) | 1976-07-30 |
| LU74883A1 (h) | 1977-01-14 |
| BR7602846A (pt) | 1976-11-16 |
| IE43133L (en) | 1976-11-07 |
| IL49515A (en) | 1979-10-31 |
| DE2620101A1 (de) | 1976-11-18 |
| NL7604764A (nl) | 1976-11-09 |
| CA1087183A (fr) | 1980-10-07 |
| BE841320A (fr) | 1976-11-03 |
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