DD151591A5 - Unkrautvertilgungsmittel-zusammensetzung - Google Patents

Unkrautvertilgungsmittel-zusammensetzung Download PDF

Info

Publication number: DD151591A5
Authority: DD; German Democratic Republic
Prior art keywords: group; antidote; carbon atoms; oxazolidine; haloalkyl
Prior art date: 1979-06-18

Application number

DD80221941A

Other languages

German (de)

English (en)

Inventor

Eugene G Teach

Original Assignee

Stauffer Chemical Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1979-06-18

Filing date

1980-06-18

Publication date

1981-10-28

1979-06-18 Priority claimed from US06/049,814 external-priority patent/US4249932A/en

1979-06-18 Priority claimed from US06/049,697 external-priority patent/US4249931A/en

1980-06-18 Application filed by Stauffer Chemical Co filed Critical Stauffer Chemical Co

1981-10-28 Publication of DD151591A5 publication Critical patent/DD151591A5/de

Links

239000000203 mixture Substances 0.000 title claims abstract description 67
239000004009 herbicide Substances 0.000 title claims abstract description 44
239000000729 antidote Substances 0.000 claims abstract description 84
-1 5-substituted oxazolidine Chemical class 0.000 claims abstract description 61
230000002363 herbicidal effect Effects 0.000 claims abstract description 37
125000000217 alkyl group Chemical group 0.000 claims abstract description 25
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 20
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 16
239000001257 hydrogen Substances 0.000 claims abstract description 10
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 9
229910052717 sulfur Chemical group 0.000 claims abstract description 9
239000011593 sulfur Chemical group 0.000 claims abstract description 9
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims abstract description 4
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims abstract description 4
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 75
125000004432 carbon atom Chemical group C* 0.000 claims description 30
239000000460 chlorine Substances 0.000 claims description 22
238000000034 method Methods 0.000 claims description 16
230000006378 damage Effects 0.000 claims description 14
229910052760 oxygen Inorganic materials 0.000 claims description 11
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
239000001301 oxygen Substances 0.000 claims description 10
GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 claims description 7
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 7
231100001184 nonphytotoxic Toxicity 0.000 claims description 7
125000001309 chloro group Chemical group Cl* 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
125000001246 bromo group Chemical group Br* 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
239000000654 additive Substances 0.000 claims description 2
239000000126 substance Substances 0.000 claims description 2
150000003558 thiocarbamic acid derivatives Chemical class 0.000 claims description 2
VFAJHTLDYCVUDP-UHFFFAOYSA-N C(C)(C)OCC1OCCN1 Chemical compound C(C)(C)OCC1OCCN1 VFAJHTLDYCVUDP-UHFFFAOYSA-N 0.000 claims 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
241000196324 Embryophyta Species 0.000 abstract description 60
239000003795 chemical substances by application Substances 0.000 abstract description 11
230000009471 action Effects 0.000 abstract description 4
101100311330 Schizosaccharomyces pombe (strain 972 / ATCC 24843) uap56 gene Proteins 0.000 abstract 1
101100072620 Streptomyces griseus ind2 gene Proteins 0.000 abstract 1
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
108090000623 proteins and genes Proteins 0.000 abstract 1
101150018444 sub2 gene Proteins 0.000 abstract 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 87
OKUGPJPKMAEJOE-UHFFFAOYSA-N S-propyl dipropylcarbamothioate Chemical compound CCCSC(=O)N(CCC)CCC OKUGPJPKMAEJOE-UHFFFAOYSA-N 0.000 description 58
239000000243 solution Substances 0.000 description 49
238000002360 preparation method Methods 0.000 description 37
238000006243 chemical reaction Methods 0.000 description 34
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 32
235000010469 Glycine max Nutrition 0.000 description 28
GUVLYNGULCJVDO-UHFFFAOYSA-N EPTC Chemical compound CCCN(CCC)C(=O)SCC GUVLYNGULCJVDO-UHFFFAOYSA-N 0.000 description 26
239000002689 soil Substances 0.000 description 25
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 21
239000000047 product Substances 0.000 description 18
238000004566 IR spectroscopy Methods 0.000 description 13
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 12
235000011114 ammonium hydroxide Nutrition 0.000 description 12
238000009331 sowing Methods 0.000 description 12
238000005481 NMR spectroscopy Methods 0.000 description 11
208000027418 Wounds and injury Diseases 0.000 description 11
208000014674 injury Diseases 0.000 description 11
YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
239000002904 solvent Substances 0.000 description 10
238000003756 stirring Methods 0.000 description 10
239000000543 intermediate Substances 0.000 description 9
229960004592 isopropanol Drugs 0.000 description 9
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 8
229940075522 antidotes Drugs 0.000 description 8
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 8
230000000694 effects Effects 0.000 description 8
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 7
101150065749 Churc1 gene Proteins 0.000 description 7
102100038239 Protein Churchill Human genes 0.000 description 7
229910021529 ammonia Inorganic materials 0.000 description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 6
239000003637 basic solution Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000007858 starting material Substances 0.000 description 6
238000010626 work up procedure Methods 0.000 description 6
239000002585 base Substances 0.000 description 5
239000013067 intermediate product Substances 0.000 description 5
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 5
238000010992 reflux Methods 0.000 description 5
238000007363 ring formation reaction Methods 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
229920001213 Polysorbate 20 Polymers 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
238000009835 boiling Methods 0.000 description 4
238000001035 drying Methods 0.000 description 4
150000002118 epoxides Chemical class 0.000 description 4
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 4
239000011521 glass Substances 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 4
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 4
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
IQHIFJVDTZSMEK-UHFFFAOYSA-N 1-chloro-3-ethylsulfanylpropan-2-ol Chemical compound CCSCC(O)CCl IQHIFJVDTZSMEK-UHFFFAOYSA-N 0.000 description 3
HWKWYDXHMQQDQJ-UHFFFAOYSA-N 2,3-dibromopropanoyl chloride Chemical compound ClC(=O)C(Br)CBr HWKWYDXHMQQDQJ-UHFFFAOYSA-N 0.000 description 3
240000006394 Sorghum bicolor Species 0.000 description 3
235000011684 Sorghum saccharatum Nutrition 0.000 description 3
239000000908 ammonium hydroxide Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 3
230000008029 eradication Effects 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
230000012010 growth Effects 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
239000007788 liquid 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
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
150000002917 oxazolidines Chemical class 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
238000006467 substitution reaction Methods 0.000 description 3
125000000446 sulfanediyl group Chemical group *S* 0.000 description 3
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
UZSDSVJEAQLMER-UHFFFAOYSA-N 1-amino-3-ethylsulfanylpropan-2-ol Chemical compound CCSCC(O)CN UZSDSVJEAQLMER-UHFFFAOYSA-N 0.000 description 2
MBYAHPCDMMPGPG-UHFFFAOYSA-N 2,2-dimethyl-5-(propan-2-yloxymethyl)-1,3-oxazolidine Chemical compound CC(C)OCC1CNC(C)(C)O1 MBYAHPCDMMPGPG-UHFFFAOYSA-N 0.000 description 2
KWLPSCOXIQJOCT-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-(methoxymethyl)-1,3-oxazolidine Chemical compound O1C(COC)CNC1C1=CC=C(Cl)C=C1 KWLPSCOXIQJOCT-UHFFFAOYSA-N 0.000 description 2
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
VVYGXCWZXQYLKD-UHFFFAOYSA-N 2-propyl-3-(3-propyloxiran-2-yl)sulfanyloxirane Chemical compound CCCC1OC1SC1C(CCC)O1 VVYGXCWZXQYLKD-UHFFFAOYSA-N 0.000 description 2
VLJQDHDVZJXNQL-UHFFFAOYSA-N 4-methyl-n-(oxomethylidene)benzenesulfonamide Chemical compound CC1=CC=C(S(=O)(=O)N=C=O)C=C1 VLJQDHDVZJXNQL-UHFFFAOYSA-N 0.000 description 2
DGEDAVCMPSTFSW-UHFFFAOYSA-N 5-(ethylsulfanylmethyl)-2,2-dimethyl-1,3-oxazolidine Chemical compound CCSCC1CNC(C)(C)O1 DGEDAVCMPSTFSW-UHFFFAOYSA-N 0.000 description 2
XOFNHZHCGBPVGJ-UHFFFAOYSA-N 5-ethyl-2-methylpiperidine Chemical compound CCC1CCC(C)NC1 XOFNHZHCGBPVGJ-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 2
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
DFCAFRGABIXSDS-UHFFFAOYSA-N Cycloate Chemical compound CCSC(=O)N(CC)C1CCCCC1 DFCAFRGABIXSDS-UHFFFAOYSA-N 0.000 description 2
244000058871 Echinochloa crus-galli Species 0.000 description 2
244000068988 Glycine max Species 0.000 description 2
244000299507 Gossypium hirsutum Species 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
101100084040 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) ppi-1 gene Proteins 0.000 description 2
101100244014 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) ppi-5 gene Proteins 0.000 description 2
FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 2
231100000674 Phytotoxicity Toxicity 0.000 description 2
240000002439 Sorghum halepense Species 0.000 description 2
229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
244000098338 Triticum aestivum Species 0.000 description 2
238000005576 amination reaction Methods 0.000 description 2
230000003042 antagnostic effect Effects 0.000 description 2
150000003935 benzaldehydes Chemical class 0.000 description 2
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical class C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
238000000576 coating method Methods 0.000 description 2
230000001276 controlling effect Effects 0.000 description 2
239000000463 material Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
229940106026 phenoxyisopropanol Drugs 0.000 description 2
238000000746 purification Methods 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000002407 reforming Methods 0.000 description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000001119 stannous chloride Substances 0.000 description 2
235000011150 stannous chloride Nutrition 0.000 description 2
238000007280 thionation reaction Methods 0.000 description 2
PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
125000006060 1,1-dimethyl-3-butenyl group Chemical group 0.000 description 1
YTPMCWYIRHLEGM-BQYQJAHWSA-N 1-[(e)-2-propylsulfonylethenyl]sulfonylpropane Chemical compound CCCS(=O)(=O)\C=C\S(=O)(=O)CCC YTPMCWYIRHLEGM-BQYQJAHWSA-N 0.000 description 1
IDSWHVZEQHESIJ-UHFFFAOYSA-N 1-amino-3-methoxypropan-2-ol Chemical compound COCC(O)CN IDSWHVZEQHESIJ-UHFFFAOYSA-N 0.000 description 1
JZEHWMUIAKALDN-UHFFFAOYSA-N 1-amino-3-phenoxypropan-2-ol Chemical compound NCC(O)COC1=CC=CC=C1 JZEHWMUIAKALDN-UHFFFAOYSA-N 0.000 description 1
125000006017 1-propenyl group Chemical group 0.000 description 1
SNQLPDDWENTOJR-UHFFFAOYSA-N 2,2-dichloro-1-[2,2-dimethyl-5-(propan-2-yloxymethyl)-1,3-oxazolidin-3-yl]ethanone Chemical compound CC(C)OCC1CN(C(=O)C(Cl)Cl)C(C)(C)O1 SNQLPDDWENTOJR-UHFFFAOYSA-N 0.000 description 1
SXRPENWRCCHDET-UHFFFAOYSA-N 2,2-dimethyl-5-(phenoxymethyl)-1,3-oxazolidine Chemical compound O1C(C)(C)NCC1COC1=CC=CC=C1 SXRPENWRCCHDET-UHFFFAOYSA-N 0.000 description 1
FKRWAFJGXXLQOY-UHFFFAOYSA-N 2,2-dimethyl-n-(4-methylphenyl)sulfonyl-5-(phenoxymethyl)-1,3-oxazolidine-3-carboxamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)N1C(C)(C)OC(COC=2C=CC=CC=2)C1 FKRWAFJGXXLQOY-UHFFFAOYSA-N 0.000 description 1
UPODEUNIWXQXLS-UHFFFAOYSA-N 2,3-dibromo-1-[5-(methoxymethyl)-2,2-dimethyl-1,3-oxazolidin-3-yl]propan-1-one Chemical compound COCC1CN(C(=O)C(Br)CBr)C(C)(C)O1 UPODEUNIWXQXLS-UHFFFAOYSA-N 0.000 description 1
CCIILNOBNOHYOX-UHFFFAOYSA-N 2-(4-chlorophenyl)-1,3-oxazolidine Chemical compound C1=CC(Cl)=CC=C1C1OCCN1 CCIILNOBNOHYOX-UHFFFAOYSA-N 0.000 description 1
NWLUZGJDEZBBRH-UHFFFAOYSA-N 2-(propan-2-yloxymethyl)oxirane Chemical compound CC(C)OCC1CO1 NWLUZGJDEZBBRH-UHFFFAOYSA-N 0.000 description 1
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
XBYCMSUMGCICIK-UHFFFAOYSA-N 2-chloro-1-[5-(ethylsulfanylmethyl)-2-phenyl-1,3-oxazolidin-3-yl]ethanone Chemical compound O1C(CSCC)CN(C(=O)CCl)C1C1=CC=CC=C1 XBYCMSUMGCICIK-UHFFFAOYSA-N 0.000 description 1
GOPUCFKUFOFEIC-UHFFFAOYSA-N 2-methyl-1,3-oxazolidine Chemical compound CC1NCCO1 GOPUCFKUFOFEIC-UHFFFAOYSA-N 0.000 description 1
HEBTZZBBPUFAFE-UHFFFAOYSA-N 2-methyl-n-(oxomethylidene)benzenesulfonamide Chemical compound CC1=CC=CC=C1S(=O)(=O)N=C=O HEBTZZBBPUFAFE-UHFFFAOYSA-N 0.000 description 1
JJJLSDKGRDVLMD-UHFFFAOYSA-N 2H-1,3-oxazol-2-ide Chemical compound O1[C-]=NC=C1 JJJLSDKGRDVLMD-UHFFFAOYSA-N 0.000 description 1
125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
OOLQCSVOGIIFNW-UHFFFAOYSA-N 5-(ethylsulfanylmethyl)-2-phenyl-1,3-oxazolidine Chemical compound O1C(CSCC)CNC1C1=CC=CC=C1 OOLQCSVOGIIFNW-UHFFFAOYSA-N 0.000 description 1
CSOLCAOHJPQVLH-UHFFFAOYSA-N 5-(methoxymethyl)-2,2-dimethyl-1,3-oxazolidine Chemical compound COCC1CNC(C)(C)O1 CSOLCAOHJPQVLH-UHFFFAOYSA-N 0.000 description 1
LCPNMGMKOBIPOV-UHFFFAOYSA-N 5-(methoxymethyl)-2-phenyl-1,3-oxazolidine Chemical compound O1C(COC)CNC1C1=CC=CC=C1 LCPNMGMKOBIPOV-UHFFFAOYSA-N 0.000 description 1
DSFRJIDTCVSLOU-UHFFFAOYSA-N 5-(phenoxymethyl)-1,3-oxazolidine Chemical compound O(C1=CC=CC=C1)CC1CNCO1 DSFRJIDTCVSLOU-UHFFFAOYSA-N 0.000 description 1
BJNKPJIMRJAXQI-UHFFFAOYSA-N 5-(propan-2-yloxymethyl)-1,3-oxazolidine Chemical compound C(C)(C)OCC1CNCO1 BJNKPJIMRJAXQI-UHFFFAOYSA-N 0.000 description 1
241000209761 Avena Species 0.000 description 1
235000007320 Avena fatua Nutrition 0.000 description 1
241000209764 Avena fatua Species 0.000 description 1
235000007319 Avena orientalis Nutrition 0.000 description 1
RAMYGXOAMNVWRX-UHFFFAOYSA-N CC1(CO1)SC1(C)CO1 Chemical compound CC1(CO1)SC1(C)CO1 RAMYGXOAMNVWRX-UHFFFAOYSA-N 0.000 description 1
QTWRSZIHSQHMOX-UHFFFAOYSA-N CCC1=C(NC([O-])=O)[S+](CC)C=C1C1CCCCC1 Chemical compound CCC1=C(NC([O-])=O)[S+](CC)C=C1C1CCCCC1 QTWRSZIHSQHMOX-UHFFFAOYSA-N 0.000 description 1
JJMWKUJHFDFXAQ-UHFFFAOYSA-N CCCC1=C[S+](CC)C(NC([O-])=O)=C1CCC Chemical compound CCCC1=C[S+](CC)C(NC([O-])=O)=C1CCC JJMWKUJHFDFXAQ-UHFFFAOYSA-N 0.000 description 1
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 description 1
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
241000234653 Cyperus Species 0.000 description 1
235000005853 Cyperus esculentus Nutrition 0.000 description 1
244000075634 Cyperus rotundus Species 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
235000009432 Gossypium hirsutum Nutrition 0.000 description 1
241000209219 Hordeum Species 0.000 description 1
240000005979 Hordeum vulgare Species 0.000 description 1
235000007340 Hordeum vulgare Nutrition 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
235000015225 Panicum colonum Nutrition 0.000 description 1
235000011999 Panicum crusgalli Nutrition 0.000 description 1
241000209504 Poaceae Species 0.000 description 1
240000003461 Setaria viridis Species 0.000 description 1
235000002248 Setaria viridis Nutrition 0.000 description 1
235000007230 Sorghum bicolor Nutrition 0.000 description 1
244000062793 Sorghum vulgare Species 0.000 description 1
235000021307 Triticum Nutrition 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
230000002159 abnormal effect Effects 0.000 description 1
150000008061 acetanilides Chemical class 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
229940069428 antacid Drugs 0.000 description 1
239000003159 antacid agent Substances 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
230000001458 anti-acid effect Effects 0.000 description 1
230000004888 barrier function Effects 0.000 description 1
230000033228 biological regulation Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
230000021235 carbamoylation Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000034303 cell budding Effects 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000012790 confirmation Methods 0.000 description 1
244000038559 crop plants Species 0.000 description 1
230000035613 defoliation Effects 0.000 description 1
230000007850 degeneration Effects 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
239000003599 detergent Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000000428 dust Substances 0.000 description 1
239000004495 emulsifiable concentrate Substances 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
244000037666 field crops Species 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000011737 fluorine Chemical group 0.000 description 1
229910052731 fluorine Chemical group 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
208000037824 growth disorder Diseases 0.000 description 1
238000003306 harvesting Methods 0.000 description 1
230000003054 hormonal effect Effects 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
230000006872 improvement Effects 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000011068 loading method Methods 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
HNEFZQHWHGZOJR-UHFFFAOYSA-N methyl 4-[2-(4-chlorophenyl)-5-(propoxymethyl)-1,3-oxazolidin-3-yl]-4-oxobutanoate Chemical compound O1C(COCCC)CN(C(=O)CCC(=O)OC)C1C1=CC=C(Cl)C=C1 HNEFZQHWHGZOJR-UHFFFAOYSA-N 0.000 description 1
FZFRDSPXVDBUMJ-UHFFFAOYSA-N methyl 4-[5-(methoxymethyl)-2-phenyl-1,3-oxazolidin-2-yl]-4-oxobutanoate Chemical compound O1C(COC)CNC1(C(=O)CCC(=O)OC)C1=CC=CC=C1 FZFRDSPXVDBUMJ-UHFFFAOYSA-N 0.000 description 1
SRXOJMOGPYFZKC-UHFFFAOYSA-N methyl 4-chloro-4-oxobutanoate Chemical compound COC(=O)CCC(Cl)=O SRXOJMOGPYFZKC-UHFFFAOYSA-N 0.000 description 1
230000005012 migration Effects 0.000 description 1
238000013508 migration Methods 0.000 description 1
238000003801 milling Methods 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000000051 modifying effect Effects 0.000 description 1
230000036651 mood Effects 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
HFHZKZSRXITVMK-UHFFFAOYSA-N oxyphenbutazone Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=C(O)C=C1 HFHZKZSRXITVMK-UHFFFAOYSA-N 0.000 description 1
229960000649 oxyphenbutazone Drugs 0.000 description 1
230000000885 phytotoxic effect Effects 0.000 description 1
230000008635 plant growth Effects 0.000 description 1
239000003223 protective agent Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
QCMHWZUFWLOOGI-UHFFFAOYSA-N s-ethyl chloromethanethioate Chemical compound CCSC(Cl)=O QCMHWZUFWLOOGI-UHFFFAOYSA-N 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
238000012549 training Methods 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
238000001665 trituration Methods 0.000 description 1
150000003672 ureas Chemical class 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/24—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/25—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
- 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
- C07D263/06—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 with hydrocarbon radicals, substituted by oxygen atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/34—Compounds containing oxirane rings with hydrocarbon radicals, substituted by sulphur, selenium or tellurium atoms

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Health & Medical Sciences (AREA)
Zoology (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
Wood Science & Technology (AREA)
Agronomy & Crop Science (AREA)
Environmental Sciences (AREA)
Toxicology (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)

DD80221941A 1979-06-18 1980-06-18 Unkrautvertilgungsmittel-zusammensetzung DD151591A5 (de)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US4967679A	1979-06-18	1979-06-18
US06/049,814 US4249932A (en)	1979-06-18	1979-06-18	5-Phenoxymethyl substituted oxazolidine herbicide antidotes
US06/049,697 US4249931A (en)	1979-06-18	1979-06-18	5-Oxy or thiomethyl substituted oxazolidine herbicide antidotes

Publications (1)

Publication Number	Publication Date
DD151591A5 true DD151591A5 (de)	1981-10-28

Family

ID=27367585

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD80221941A DD151591A5 (de)	1979-06-18	1980-06-18	Unkrautvertilgungsmittel-zusammensetzung

Country Status (18)

Country	Link
EP (1)	EP0021759B1 (fr)
KR (1)	KR840000857B1 (fr)
AR (1)	AR228034A1 (fr)
AU (1)	AU537415B2 (fr)
BG (1)	BG36626A3 (fr)
BR (1)	BR8003659A (fr)
CA (1)	CA1149393A (fr)
DD (1)	DD151591A5 (fr)
DE (1)	DE3069274D1 (fr)
DK (1)	DK260680A (fr)
ES (5)	ES492500A0 (fr)
IL (1)	IL60333A (fr)
NZ (1)	NZ194070A (fr)
PH (1)	PH19088A (fr)
PL (1)	PL124586B1 (fr)
PT (1)	PT71407A (fr)
RO (1)	RO81224B (fr)
TR (1)	TR20378A (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BR8205085A (pt) *	1981-09-08	1983-08-09	Stauffer Chemical Co	Composicao de antidoto herbicida e processo para estabelecer seletividade herbicida
PL144076B1 (en) *	1983-08-24	1988-04-30	Stauffer Chemical Co	Herbicide
IT1196507B (it) *	1986-07-16	1988-11-16	Oxon Italia Spa	5-imminometil-aloacilossazolidone ad azione inibitrice della fitotossicita' di erbicidi
ATE181735T1 (de) *	1993-05-01	1999-07-15	Merck Patent Gmbh	Substituierte 1-phenyl-oxazolidin-2-on derivate, deren herstellung und deren verwendung als adhäsionsrezeptor-antagonisten

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3959304A (en) *	1974-07-01	1976-05-25	Stauffer Chemical Company	Certain 3-haloacyl-2,2,5-trimethyl-oxazolidines
US4072688A (en) *	1975-02-14	1978-02-07	Stauffer Chemical Company	Haloacyl and thiohaloacyl aryl-substituted oxazolidines and thiazolidines-herbicidal antidotes

1980
- 1980-01-16 AR AR281424A patent/AR228034A1/es active
- 1980-06-12 BR BR8003659A patent/BR8003659A/pt unknown
- 1980-06-13 AU AU59291/80A patent/AU537415B2/en not_active Ceased
- 1980-06-14 RO RO101418A patent/RO81224B/ro unknown
- 1980-06-16 DE DE8080302017T patent/DE3069274D1/de not_active Expired
- 1980-06-16 EP EP80302017A patent/EP0021759B1/fr not_active Expired
- 1980-06-16 CA CA000354070A patent/CA1149393A/fr not_active Expired
- 1980-06-16 BG BG048157A patent/BG36626A3/xx unknown
- 1980-06-17 PH PH24156A patent/PH19088A/en unknown
- 1980-06-17 TR TR20378A patent/TR20378A/xx unknown
- 1980-06-17 IL IL60333A patent/IL60333A/xx unknown
- 1980-06-17 ES ES492500A patent/ES492500A0/es active Granted
- 1980-06-17 NZ NZ194070A patent/NZ194070A/en unknown
- 1980-06-18 PL PL1980225057A patent/PL124586B1/pl unknown
- 1980-06-18 DD DD80221941A patent/DD151591A5/de unknown
- 1980-06-18 DK DK260680A patent/DK260680A/da not_active Application Discontinuation
- 1980-06-18 PT PT71407A patent/PT71407A/pt unknown
1981
- 1981-02-16 ES ES499467A patent/ES8201559A1/es not_active Expired
- 1981-02-16 ES ES499465A patent/ES499465A0/es active Granted
- 1981-02-16 ES ES499464A patent/ES8201557A1/es not_active Expired
- 1981-02-16 ES ES499466A patent/ES8201558A1/es not_active Expired
1984
- 1984-04-17 KR KR1019840002027A patent/KR840000857B1/ko not_active Expired

Also Published As

Publication number	Publication date
TR20378A (tr)	1981-05-01
DE3069274D1 (en)	1984-10-31
KR840000857B1 (ko)	1984-06-20
BR8003659A (pt)	1981-08-04
ES499467A0 (es)	1981-12-16
ES8204988A1 (es)	1982-05-16
AU5929180A (en)	1981-01-08
ES8105305A1 (es)	1981-06-01
IL60333A (en)	1984-12-31
IL60333A0 (en)	1980-09-16
PL124586B1 (en)	1983-02-28
PL225057A1 (fr)	1981-03-27
AU537415B2 (en)	1984-06-21
NZ194070A (en)	1984-11-09
PH19088A (en)	1985-12-19
DK260680A (da)	1980-12-19
EP0021759A1 (fr)	1981-01-07
AR228034A1 (es)	1983-01-14
CA1149393A (fr)	1983-07-05
RO81224B (ro)	1983-02-28
ES499466A0 (es)	1981-12-16
ES499464A0 (es)	1981-12-16
RO81224A (fr)	1983-02-15
ES8201558A1 (es)	1981-12-16
ES492500A0 (es)	1981-06-01
ES499465A0 (es)	1982-05-16
EP0021759B1 (fr)	1984-09-26
ES8201559A1 (es)	1981-12-16
ES8201557A1 (es)	1981-12-16
PT71407A (en)	1980-07-01
BG36626A3 (en)	1984-12-16

Publication	Publication Date	Title
EP0012158B1 (fr)	1984-08-15	Dérivés d'oxime et leur utilisation dans la protection des cultures de plantes
DE2360631A1 (de)	1974-06-12	1,2,4-triazolylphosphorsaeure- bzw. phosphonsaeureester, verfahren zu ihrer herstellung und ihre verwendung
CH633260A5 (de)	1982-11-30	N'-(4-phenylaethyloxyphenyl)-n-methyl-n-methoxyharnstoffe, bei denen der phenylrest des phenylaethylrestes substituiert ist.
CH636853A5 (de)	1983-06-30	N'-phenyl-n-methylharnstoffderivate, verfahren zur herstellung und verwendung derselben.
JPS5829281B2 (ja)	1983-06-22	バルビツ−ル酸系除草剤
DE2605586C2 (fr)	1988-01-14
DD231978A5 (de)	1986-01-15	Herbizide zusammensetzung
DE2952483C2 (de)	1983-06-23	O-Sulfamoylglykolsäureamid-Derivate und deren Verwendung in einem herbiziden Mittel
JPS585900B2 (ja)	1983-02-02	新規ジフェニルエ−テル系化合物と殺草剤
US4400529A (en)	1983-08-23	Herbicide antidote compositions and method of use
DE2362333C3 (de)	1978-07-13	Thionophosphorsäureesteramide, Verfahren zu deren Herstellung und Verwendung derselben
DE2634278A1 (de)	1977-02-24	Unkrautvertilgungsmittel, die dibromsubstituierte propionamide als antidots enthalten
US3647850A (en)	1972-03-07	Fluorine substituted benzyl dithiocarbamates and their production and use
DE2519085C3 (de)	1978-05-18	Substituierte Benzolmethanolverbindungen und diese enthaltende herbizide Mittel
PL124586B1 (en)	1983-02-28	Herbicide with detoxicant
CH629081A5 (en)	1982-04-15	Herbicidal composition
DE2356892A1 (de)	1974-06-06	Alpha-pyron-derivate, ihre herstellung und ihre verwendung als selektivherbicide, pflanzenwachstumsregulatoren und fungicide
US4351665A (en)	1982-09-28	Sulfinoate herbicidal antidotes
US4279638A (en)	1981-07-21	3,5-Disubstituted 1,2,4-oxadiazole herbicidal antidotes
DE2260763A1 (de)	1973-06-20	Mittel zum abtoeten von schaedlichen organismen
KR830002894B1 (ko)	1983-12-30	피리다진 유도체의 제조방법
DE2431801C3 (de)	1976-09-23	Benzothiazolderivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur selektiven Unkrautbekämpfung in Reis- oder Weizenkulturen
AT328795B (de)	1976-04-12	Schadlingsbekampfungsmittel
JPS58206555A (ja)	1983-12-01	シクロヘキセノン誘導体、その製造方法及び選択的除草剤
DE2451418B2 (de)	1977-02-24	N-alpha, alpha-dimethylbenzyl-n'- phenyl-n'-alkoxy-bzw. n'-alkenyloxy- harnstoffe und diese enthaltende herbicide mittel