HU176867B - Composition containing herbicide active material of thiocarbamate type and antidote of oxazolidine type - Google Patents
Composition containing herbicide active material of thiocarbamate type and antidote of oxazolidine type Download PDFInfo
- Publication number
- HU176867B HU176867B HU76SA2884A HUSA002884A HU176867B HU 176867 B HU176867 B HU 176867B HU 76SA2884 A HU76SA2884 A HU 76SA2884A HU SA002884 A HUSA002884 A HU SA002884A HU 176867 B HU176867 B HU 176867B
- Authority
- HU
- Hungary
- Prior art keywords
- antidote
- compound
- hydrogen
- priority
- composition
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 66
- 239000000729 antidote Substances 0.000 title claims abstract description 54
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 32
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 title claims description 6
- 239000004009 herbicide Substances 0.000 title description 32
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 title description 3
- 239000011149 active material Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 75
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 125000001188 haloalkyl group Chemical group 0.000 claims description 22
- 239000004480 active ingredient Substances 0.000 claims description 9
- -1 chloro, nitro, methyl Chemical group 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 239000004927 clay Substances 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 4
- 239000003350 kerosene Substances 0.000 claims description 4
- 239000008096 xylene Substances 0.000 claims description 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 3
- 239000003945 anionic surfactant Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000008187 granular material Substances 0.000 claims description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000002736 nonionic surfactant Substances 0.000 claims description 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000005909 Kieselgur Substances 0.000 claims description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 239000000440 bentonite Substances 0.000 claims description 2
- 229910000278 bentonite Inorganic materials 0.000 claims description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000002091 cationic group Chemical group 0.000 claims description 2
- 239000003093 cationic surfactant Substances 0.000 claims description 2
- 229910052570 clay Inorganic materials 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 239000000295 fuel oil Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims description 2
- 229910052903 pyrophyllite Inorganic materials 0.000 claims description 2
- 239000000454 talc Substances 0.000 claims description 2
- 229910052623 talc Inorganic materials 0.000 claims description 2
- 229910052902 vermiculite Inorganic materials 0.000 claims description 2
- 239000010455 vermiculite Substances 0.000 claims description 2
- 235000019354 vermiculite Nutrition 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 125000000068 chlorophenyl group Chemical group 0.000 claims 3
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 230000003179 granulation Effects 0.000 claims 2
- 238000005469 granulation Methods 0.000 claims 2
- 125000006501 nitrophenyl group Chemical group 0.000 claims 2
- 239000003208 petroleum Substances 0.000 claims 2
- 206010029897 Obsessive thoughts Diseases 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims 1
- 150000002790 naphthalenes Chemical class 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 15
- OKUGPJPKMAEJOE-UHFFFAOYSA-N S-propyl dipropylcarbamothioate Chemical compound CCCSC(=O)N(CCC)CCC OKUGPJPKMAEJOE-UHFFFAOYSA-N 0.000 description 63
- GUVLYNGULCJVDO-UHFFFAOYSA-N EPTC Chemical compound CCCN(CCC)C(=O)SCC GUVLYNGULCJVDO-UHFFFAOYSA-N 0.000 description 52
- 240000008042 Zea mays Species 0.000 description 40
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 40
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 40
- 235000009973 maize Nutrition 0.000 description 40
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 25
- 240000006394 Sorghum bicolor Species 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 21
- 241000209219 Hordeum Species 0.000 description 19
- 235000007340 Hordeum vulgare Nutrition 0.000 description 19
- 241000196324 Embryophyta Species 0.000 description 17
- 239000011550 stock solution Substances 0.000 description 17
- 239000002689 soil Substances 0.000 description 14
- 241000209094 Oryza Species 0.000 description 13
- 235000007164 Oryza sativa Nutrition 0.000 description 13
- 235000009566 rice Nutrition 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 9
- 229940075522 antidotes Drugs 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 125000001309 chloro group Chemical group Cl* 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 241000607479 Yersinia pestis Species 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 241000209140 Triticum Species 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 244000020551 Helianthus annuus Species 0.000 description 4
- 235000003222 Helianthus annuus Nutrition 0.000 description 4
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 230000010534 mechanism of action Effects 0.000 description 4
- 238000009331 sowing Methods 0.000 description 4
- 241000894007 species Species 0.000 description 4
- PMRFVAVTJBHLIX-UHFFFAOYSA-N 2,2-dichloro-1-[2-(3-nitrophenyl)-1,3-oxazolidin-3-yl]ethanone Chemical compound [O-][N+](=O)C1=CC=CC(C2N(CCO2)C(=O)C(Cl)Cl)=C1 PMRFVAVTJBHLIX-UHFFFAOYSA-N 0.000 description 3
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 3
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 3
- 235000021536 Sugar beet Nutrition 0.000 description 3
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 244000038559 crop plants Species 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000008654 plant damage Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 2
- UFXKOCRVIUQSGA-UHFFFAOYSA-N 2,2-dichloro-1-(2,2,4-trimethyl-5-phenyl-1,3-oxazolidin-3-yl)ethanone Chemical compound O1C(C)(C)N(C(=O)C(Cl)Cl)C(C)C1C1=CC=CC=C1 UFXKOCRVIUQSGA-UHFFFAOYSA-N 0.000 description 2
- SXSNYZPSATVORJ-UHFFFAOYSA-N 2,2-dichloro-1-(2,2-dimethyl-5-phenyl-1,3-oxazolidin-3-yl)ethanone Chemical compound C1N(C(=O)C(Cl)Cl)C(C)(C)OC1C1=CC=CC=C1 SXSNYZPSATVORJ-UHFFFAOYSA-N 0.000 description 2
- FWTCEPSLRAJZDH-UHFFFAOYSA-N 2,2-dichloro-1-(2-ethyl-5-phenyl-1,3-oxazolidin-3-yl)ethanone Chemical compound C1N(C(=O)C(Cl)Cl)C(CC)OC1C1=CC=CC=C1 FWTCEPSLRAJZDH-UHFFFAOYSA-N 0.000 description 2
- PVHYHJXYSJZUIN-UHFFFAOYSA-N 2,2-dichloro-1-[2-(4-chlorophenyl)-1,3-oxazolidin-3-yl]ethanone Chemical compound ClC(Cl)C(=O)N1CCOC1C1=CC=C(Cl)C=C1 PVHYHJXYSJZUIN-UHFFFAOYSA-N 0.000 description 2
- OWJQTDFFYOQKIX-UHFFFAOYSA-N 3-bromo-1-(5-phenyl-1,3-oxazolidin-3-yl)propan-1-one Chemical compound C1N(C(=O)CCBr)COC1C1=CC=CC=C1 OWJQTDFFYOQKIX-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
- DFCAFRGABIXSDS-UHFFFAOYSA-N Cycloate Chemical compound CCSC(=O)N(CC)C1CCCCC1 DFCAFRGABIXSDS-UHFFFAOYSA-N 0.000 description 2
- 240000004585 Dactylis glomerata Species 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- QHTQREMOGMZHJV-UHFFFAOYSA-N Thiobencarb Chemical compound CCN(CC)C(=O)SCC1=CC=C(Cl)C=C1 QHTQREMOGMZHJV-UHFFFAOYSA-N 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229940126208 compound 22 Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 239000003815 herbicide antidote Substances 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 150000002917 oxazolidines Chemical class 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
- 238000004381 surface treatment Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 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
- GSJWOQQDBDJRHN-UHFFFAOYSA-N 2,2,4-trimethyl-5-phenyl-1,3-oxazolidine Chemical compound CC1NC(C)(C)OC1C1=CC=CC=C1 GSJWOQQDBDJRHN-UHFFFAOYSA-N 0.000 description 1
- UFAPZWVTKMHNOL-UHFFFAOYSA-N 2,3-dibromo-1-(2,5-diphenyl-1,3-oxazolidin-3-yl)propan-1-one Chemical compound BrCC(Br)C(=O)N1CC(C=2C=CC=CC=2)OC1C1=CC=CC=C1 UFAPZWVTKMHNOL-UHFFFAOYSA-N 0.000 description 1
- HWKWYDXHMQQDQJ-UHFFFAOYSA-N 2,3-dibromopropanoyl chloride Chemical compound ClC(=O)C(Br)CBr HWKWYDXHMQQDQJ-UHFFFAOYSA-N 0.000 description 1
- JSTLZWSXHWARBN-UHFFFAOYSA-N 2,5-diphenyl-1,3-oxazolidine Chemical compound C1NC(C=2C=CC=CC=2)OC1C1=CC=CC=C1 JSTLZWSXHWARBN-UHFFFAOYSA-N 0.000 description 1
- VEXOEZYUONWVFH-UHFFFAOYSA-N 2-(3-nitrophenyl)-1,3-oxazolidine Chemical compound [O-][N+](=O)C1=CC=CC(C2OCCN2)=C1 VEXOEZYUONWVFH-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
- VVCMGAUPZIKYTH-VGHSCWAPSA-N 2-acetyloxybenzoic acid;[(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;1,3,7-trimethylpurine-2,6-dione Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VVCMGAUPZIKYTH-VGHSCWAPSA-N 0.000 description 1
- WIYIBHOHIPAIJB-UHFFFAOYSA-N 2-chloro-1-(4,4-dimethyl-2-phenyl-1,3-oxazolidin-3-yl)ethanone Chemical compound ClCC(=O)N1C(C)(C)COC1C1=CC=CC=C1 WIYIBHOHIPAIJB-UHFFFAOYSA-N 0.000 description 1
- GNNBYMVRNDJJRY-UHFFFAOYSA-N 2-ethyl-5-phenyl-1,3-oxazolidine Chemical compound O1C(CC)NCC1C1=CC=CC=C1 GNNBYMVRNDJJRY-UHFFFAOYSA-N 0.000 description 1
- ZYUWGAVXDLKUKT-UHFFFAOYSA-N 4,4-dimethyl-2-phenyl-1,3-oxazolidine Chemical compound N1C(C)(C)COC1C1=CC=CC=C1 ZYUWGAVXDLKUKT-UHFFFAOYSA-N 0.000 description 1
- HGRPZJNLVMLELR-UHFFFAOYSA-N 5-phenyl-1,3-oxazolidine Chemical compound O1CNCC1C1=CC=CC=C1 HGRPZJNLVMLELR-UHFFFAOYSA-N 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000006008 Brassica napus var napus Nutrition 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 235000015505 Sorghum bicolor subsp. bicolor Nutrition 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- MWBPRDONLNQCFV-UHFFFAOYSA-N Tri-allate Chemical compound CC(C)N(C(C)C)C(=O)SCC(Cl)=C(Cl)Cl MWBPRDONLNQCFV-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 150000008061 acetanilides Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000002303 anti-venom Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- LDOPKOBZIPJHTP-UHFFFAOYSA-N azepine-1-carbothioic s-acid Chemical compound OC(=S)N1C=CC=CC=C1 LDOPKOBZIPJHTP-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- NCPDPTXSMJDCIH-UHFFFAOYSA-N dipropylcarbamothioic s-acid Chemical compound CCCN(C(S)=O)CCC NCPDPTXSMJDCIH-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004049 embossing Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 125000000262 haloalkenyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 230000000051 modifying effect Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical compound NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 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
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 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
- 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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55006975A | 1975-02-14 | 1975-02-14 | |
| US05/627,986 US4072688A (en) | 1975-02-14 | 1975-11-03 | Haloacyl and thiohaloacyl aryl-substituted oxazolidines and thiazolidines-herbicidal antidotes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU176867B true HU176867B (en) | 1981-05-28 |
Family
ID=27069322
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU76SA2884A HU176867B (en) | 1975-02-14 | 1976-02-09 | Composition containing herbicide active material of thiocarbamate type and antidote of oxazolidine type |
| HU76SA3092A HU184694B (en) | 1975-02-14 | 1976-02-09 | Herbicide composition containing a herbide active substance of thiocaraamate or acetanilide type and an antidote of thiazolidine type |
| HU76SA3169A HU181492B (en) | 1975-02-14 | 1976-02-09 | Composition containing acetanilide type herbicide agent and antidote |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU76SA3092A HU184694B (en) | 1975-02-14 | 1976-02-09 | Herbicide composition containing a herbide active substance of thiocaraamate or acetanilide type and an antidote of thiazolidine type |
| HU76SA3169A HU181492B (en) | 1975-02-14 | 1976-02-09 | Composition containing acetanilide type herbicide agent and antidote |
Country Status (23)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH640108A5 (de) * | 1978-02-06 | 1983-12-30 | Nitrokemia Ipartelepek | Unkrautvernichtungsmittel. |
| HU178301B (en) * | 1978-02-06 | 1982-04-28 | Nitrokemia Ipartelepek | Herbicide compositions containing naphthaline-carboxylic acid derivatives as antidotes and carbamide derivatives and antidote compositions containing naphthaline-carboxylic acid derivatives |
| US4199506A (en) * | 1978-05-15 | 1980-04-22 | Monsanto Company | 2,4-Disubstituted-5-thiazolecarboxylic acids and derivatives |
| US5225570A (en) * | 1987-08-13 | 1993-07-06 | Monsanto Company | 5-heterocyclic-substituted oxazolidine dihaloacetamides |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| GB1420685A (en) * | 1972-08-15 | 1976-01-07 | Scm Corp | Substituted oxazolidines |
| US3884671A (en) * | 1972-08-15 | 1975-05-20 | Scm Corp | Herbicidal n-haloacyl (2-alkylated) oxazolidines |
| CA1014563A (en) * | 1972-10-13 | 1977-07-26 | Stauffer Chemical Company | Substituted oxazolidines and thiazolidines |
-
1976
- 1976-02-06 BR BR7600775A patent/BR7600775A/pt unknown
- 1976-02-09 HU HU76SA2884A patent/HU176867B/hu unknown
- 1976-02-09 HU HU76SA3092A patent/HU184694B/hu unknown
- 1976-02-09 HU HU76SA3169A patent/HU181492B/hu unknown
- 1976-02-10 FR FR7603577A patent/FR2309546A1/fr active Granted
- 1976-02-10 TR TR18817A patent/TR18817A/xx unknown
- 1976-02-11 EG EG70/76A patent/EG11942A/xx active
- 1976-02-11 CH CH166876A patent/CH617570A5/de not_active IP Right Cessation
- 1976-02-12 RO RO7684794A patent/RO75509A/ro unknown
- 1976-02-12 IT IT48066/76A patent/IT1053846B/it active
- 1976-02-12 DE DE19762605586 patent/DE2605586A1/de active Granted
- 1976-02-12 IL IL49023A patent/IL49023A/xx unknown
- 1976-02-12 SU SU762324802A patent/SU661991A3/ru active
- 1976-02-12 DD DD191217A patent/DD122921A5/xx unknown
- 1976-02-12 GB GB5544/76A patent/GB1484842A/en not_active Expired
- 1976-02-13 AU AU11116/76A patent/AU502808B2/en not_active Expired
- 1976-02-13 CA CA245,696A patent/CA1072566A/en not_active Expired
- 1976-02-13 JP JP51014787A patent/JPS5259153A/ja active Pending
- 1976-02-13 DK DK59276*#A patent/DK59276A/da not_active Application Discontinuation
- 1976-02-13 AR AR262257A patent/AR217050A1/es active
- 1976-02-13 NL NLAANVRAGE7601500,A patent/NL188577C/xx not_active IP Right Cessation
- 1976-02-13 ES ES445173A patent/ES445173A1/es not_active Expired
- 1976-02-14 PL PL1976187228A patent/PL100027B1/pl unknown
-
1977
- 1977-06-27 AR AR268195A patent/AR227500A1/es active
-
1979
- 1979-12-13 CH CH1105179A patent/CH619599A5/de not_active IP Right Cessation
- 1979-12-13 CH CH1105279A patent/CH624554A5/de not_active IP Right Cessation
-
1980
- 1980-04-10 KE KE3041A patent/KE3041A/xx unknown
- 1980-12-30 MY MY229/80A patent/MY8000229A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH624554A5 (en) | 1981-08-14 |
| NL188577C (nl) | 1992-08-03 |
| CH617570A5 (en) | 1980-06-13 |
| KE3041A (en) | 1980-04-25 |
| NL7601500A (nl) | 1976-08-17 |
| IL49023A0 (en) | 1976-04-30 |
| DD122921A5 (de) | 1976-11-12 |
| FR2309546B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-05-16 |
| EG11942A (en) | 1978-03-29 |
| CA1072566A (en) | 1980-02-26 |
| AR217050A1 (es) | 1980-02-29 |
| TR18817A (tr) | 1977-11-01 |
| DE2605586A1 (de) | 1976-08-26 |
| IL49023A (en) | 1979-01-31 |
| HU184694B (en) | 1984-09-28 |
| BR7600775A (pt) | 1977-05-10 |
| FR2309546A1 (fr) | 1976-11-26 |
| PL100027B1 (pl) | 1978-08-31 |
| JPS5259153A (en) | 1977-05-16 |
| IT1053846B (it) | 1981-10-10 |
| HU181492B (en) | 1983-07-28 |
| ES445173A1 (es) | 1977-09-16 |
| SU661991A3 (ru) | 1979-05-05 |
| MY8000229A (en) | 1980-12-31 |
| CH619599A5 (en) | 1980-10-15 |
| AU1111676A (en) | 1977-08-18 |
| DK59276A (da) | 1976-08-15 |
| GB1484842A (en) | 1977-09-08 |
| RO75509A (ro) | 1980-12-30 |
| AR227500A1 (es) | 1982-11-15 |
| DE2605586C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-01-14 |
| AU502808B2 (en) | 1979-08-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HPC4 | Succession in title of patentee |
Owner name: ZENECA INC, US |