CA1236463A - Herbicidal 1-aryl-.delta..sup.2-1,2,4-triazolin-5-ones - Google Patents
Herbicidal 1-aryl-.delta..sup.2-1,2,4-triazolin-5-onesInfo
- Publication number
- CA1236463A CA1236463A CA000465372A CA465372A CA1236463A CA 1236463 A CA1236463 A CA 1236463A CA 000465372 A CA000465372 A CA 000465372A CA 465372 A CA465372 A CA 465372A CA 1236463 A CA1236463 A CA 1236463A
- Authority
- CA
- Canada
- Prior art keywords
- ylmethyl
- methyl
- alkyl
- carbon atoms
- compound
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 46
- 150000001875 compounds Chemical class 0.000 claims abstract description 92
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 65
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 29
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 26
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 25
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 25
- 229910052717 sulfur Chemical group 0.000 claims abstract description 25
- 239000011593 sulfur Chemical group 0.000 claims abstract description 25
- 150000002367 halogens Chemical class 0.000 claims abstract description 24
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 24
- 239000001301 oxygen Substances 0.000 claims abstract description 24
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 21
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 20
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 19
- 125000004966 cyanoalkyl group Chemical group 0.000 claims abstract description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims abstract description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 6
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 6
- 229910052757 nitrogen Chemical group 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- -1 alkyl radical Chemical class 0.000 claims description 232
- 239000000460 chlorine Substances 0.000 claims description 127
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 82
- 239000000203 mixture Substances 0.000 claims description 76
- 125000004432 carbon atom Chemical group C* 0.000 claims description 53
- 229910052801 chlorine Inorganic materials 0.000 claims description 31
- 235000017168 chlorine Nutrition 0.000 claims description 31
- 244000068988 Glycine max Species 0.000 claims description 26
- 235000010469 Glycine max Nutrition 0.000 claims description 26
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 24
- 229920000742 Cotton Polymers 0.000 claims description 21
- 241000219146 Gossypium Species 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 19
- 239000011737 fluorine Substances 0.000 claims description 18
- 229910052731 fluorine Inorganic materials 0.000 claims description 18
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 6
- HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 claims description 4
- 240000008042 Zea mays Species 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 4
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 4
- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical group OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 230000008635 plant growth Effects 0.000 claims description 4
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 3
- 235000005822 corn Nutrition 0.000 claims description 3
- 229960005419 nitrogen Drugs 0.000 claims description 3
- 229940060038 chlorine Drugs 0.000 claims 22
- 229940060037 fluorine Drugs 0.000 claims 12
- 235000019000 fluorine Nutrition 0.000 claims 12
- 229940074995 bromine Drugs 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 92
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 66
- 238000001228 spectrum Methods 0.000 description 65
- 239000000047 product Substances 0.000 description 62
- 239000011541 reaction mixture Substances 0.000 description 55
- 239000000243 solution Substances 0.000 description 55
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- 239000003921 oil Substances 0.000 description 35
- 235000019198 oils Nutrition 0.000 description 35
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 33
- 239000012312 sodium hydride Substances 0.000 description 33
- 229910000104 sodium hydride Inorganic materials 0.000 description 33
- 239000007787 solid Substances 0.000 description 30
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
- 238000010992 reflux Methods 0.000 description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
- 240000007594 Oryza sativa Species 0.000 description 24
- 235000007164 Oryza sativa Nutrition 0.000 description 24
- 241000209140 Triticum Species 0.000 description 24
- 235000021307 Triticum Nutrition 0.000 description 24
- 240000006995 Abutilon theophrasti Species 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 23
- 235000009566 rice Nutrition 0.000 description 23
- 235000003403 Limnocharis flava Nutrition 0.000 description 22
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 21
- 240000002439 Sorghum halepense Species 0.000 description 21
- 241000482268 Zea mays subsp. mays Species 0.000 description 21
- 239000000706 filtrate Substances 0.000 description 20
- 235000005853 Cyperus esculentus Nutrition 0.000 description 19
- 244000058871 Echinochloa crus-galli Species 0.000 description 19
- 240000001549 Ipomoea eriocarpa Species 0.000 description 19
- 235000005146 Ipomoea eriocarpa Nutrition 0.000 description 19
- 240000001505 Cyperus odoratus Species 0.000 description 18
- 238000007792 addition Methods 0.000 description 18
- 238000004458 analytical method Methods 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 235000002248 Setaria viridis Nutrition 0.000 description 15
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 15
- 235000010086 Setaria viridis var. viridis Nutrition 0.000 description 14
- 229910052739 hydrogen Inorganic materials 0.000 description 14
- 239000001257 hydrogen Substances 0.000 description 14
- 241000894007 species Species 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- 240000003461 Setaria viridis Species 0.000 description 13
- 229960000443 hydrochloric acid Drugs 0.000 description 13
- 235000011167 hydrochloric acid Nutrition 0.000 description 13
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 13
- 235000019341 magnesium sulphate Nutrition 0.000 description 13
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 12
- 235000011121 sodium hydroxide Nutrition 0.000 description 12
- 229940083608 sodium hydroxide Drugs 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 238000009472 formulation Methods 0.000 description 11
- WWCNXHYRAKUQDB-UHFFFAOYSA-N oxolan-3-yl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC1COCC1 WWCNXHYRAKUQDB-UHFFFAOYSA-N 0.000 description 11
- 229940107700 pyruvic acid Drugs 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000002689 soil Substances 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
- 239000000543 intermediate Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- VOHILFSOWRNVJJ-UHFFFAOYSA-N 2-(bromomethyl)oxolane Chemical compound BrCC1CCCO1 VOHILFSOWRNVJJ-UHFFFAOYSA-N 0.000 description 7
- 241000196324 Embryophyta Species 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000002270 dispersing agent Substances 0.000 description 7
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 241000207892 Convolvulus Species 0.000 description 6
- 101100495923 Schizosaccharomyces pombe (strain 972 / ATCC 24843) chr2 gene Proteins 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- ZHZYGIQVBQWOJJ-UHFFFAOYSA-N 3,4-dihydro-1,2,4-triazol-5-one Chemical compound O=C1NCN=N1 ZHZYGIQVBQWOJJ-UHFFFAOYSA-N 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 239000011550 stock solution Substances 0.000 description 5
- XKJYXTZFPVNQGG-UHFFFAOYSA-N 1-(3-hydroxyphenyl)-4h-triazol-5-one Chemical class OC1=CC=CC(N2C(CN=N2)=O)=C1 XKJYXTZFPVNQGG-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 235000011054 acetic acid Nutrition 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229940093956 potassium carbonate Drugs 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 235000011181 potassium carbonates Nutrition 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000012265 solid product Substances 0.000 description 4
- 239000012258 stirred mixture Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- KPIOFCJOKUHZPF-UHFFFAOYSA-N (3-methoxyphenyl)hydrazine Chemical compound COC1=CC=CC(NN)=C1 KPIOFCJOKUHZPF-UHFFFAOYSA-N 0.000 description 3
- BIERXSDNSFWBLQ-UHFFFAOYSA-N (4-chloro-2-fluoro-5-methoxyphenyl)hydrazine Chemical compound COC1=CC(NN)=C(F)C=C1Cl BIERXSDNSFWBLQ-UHFFFAOYSA-N 0.000 description 3
- WNWOTMKHOLCHRJ-UHFFFAOYSA-N 1,4-dihydrotriazol-5-one Chemical compound O=C1CN=NN1 WNWOTMKHOLCHRJ-UHFFFAOYSA-N 0.000 description 3
- CEFVCNWQCJCMHZ-UHFFFAOYSA-N 2-(bromomethyl)furan Chemical compound BrCC1=CC=CO1 CEFVCNWQCJCMHZ-UHFFFAOYSA-N 0.000 description 3
- ZBUDAHCMQUETEO-UHFFFAOYSA-N 4-chloro-2-fluoro-5-methoxyaniline Chemical compound COC1=CC(N)=C(F)C=C1Cl ZBUDAHCMQUETEO-UHFFFAOYSA-N 0.000 description 3
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000004009 herbicide Substances 0.000 description 3
- 150000004678 hydrides Chemical class 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
- 239000012085 test solution Substances 0.000 description 3
- 231100000167 toxic agent Toxicity 0.000 description 3
- 239000003440 toxic substance Substances 0.000 description 3
- AVLKYCMLUHXGOX-UHFFFAOYSA-N (1-methylpyrrolidin-3-yl) 4-methylbenzenesulfonate Chemical compound C1N(C)CCC1OS(=O)(=O)C1=CC=C(C)C=C1 AVLKYCMLUHXGOX-UHFFFAOYSA-N 0.000 description 2
- MPNNLCONPWKVOX-UHFFFAOYSA-N (2,2-dimethyl-1,3-dithiolan-4-yl)methanol Chemical compound CC1(C)SCC(CO)S1 MPNNLCONPWKVOX-UHFFFAOYSA-N 0.000 description 2
- AMMSEPFGEHQNFD-UHFFFAOYSA-N (3-methoxy-4-methylphenyl)hydrazine Chemical compound COC1=CC(NN)=CC=C1C AMMSEPFGEHQNFD-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- OTGAYUCEDFKLHW-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxin-3-ylmethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1OC2=CC=CC=C2OC1 OTGAYUCEDFKLHW-UHFFFAOYSA-N 0.000 description 2
- CKIIJIDEWWXQEA-UHFFFAOYSA-N 2-(bromomethyl)-1,3-dioxolane Chemical compound BrCC1OCCO1 CKIIJIDEWWXQEA-UHFFFAOYSA-N 0.000 description 2
- TYEYBOSBBBHJIV-UHFFFAOYSA-N 2-oxobutanoic acid Chemical compound CCC(=O)C(O)=O TYEYBOSBBBHJIV-UHFFFAOYSA-N 0.000 description 2
- SGFKSWJIHZQDSJ-UHFFFAOYSA-N 4-(chloromethyl)-2,2-dimethyl-1,3-dithiolane Chemical compound CC1(C)SCC(CCl)S1 SGFKSWJIHZQDSJ-UHFFFAOYSA-N 0.000 description 2
- FZNORVZNZXGAMJ-UHFFFAOYSA-N 5-(chloromethyl)-3,6-dihydro-2h-pyran Chemical compound ClCC1=CCCOC1 FZNORVZNZXGAMJ-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 description 2
- 231100000674 Phytotoxicity Toxicity 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000020335 dealkylation Effects 0.000 description 2
- 238000006900 dealkylation reaction Methods 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
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- 239000012259 ether extract Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 244000304962 green bristle grass Species 0.000 description 2
- 125000000262 haloalkenyl group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- ZEERHWXRRLRIQO-UHFFFAOYSA-N oxan-4-yl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC1CCOCC1 ZEERHWXRRLRIQO-UHFFFAOYSA-N 0.000 description 2
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 2
- 229940067157 phenylhydrazine Drugs 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- GDJWDLUJZROSRN-UHFFFAOYSA-N thian-4-yl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC1CCSCC1 GDJWDLUJZROSRN-UHFFFAOYSA-N 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- AEFDFEJGVXDJEB-UHFFFAOYSA-N thiolan-3-yl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC1CSCC1 AEFDFEJGVXDJEB-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
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- 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 1
- LZTSCEYDCZBRCJ-UHFFFAOYSA-N 1,2-dihydro-1,2,4-triazol-3-one Chemical compound OC=1N=CNN=1 LZTSCEYDCZBRCJ-UHFFFAOYSA-N 0.000 description 1
- RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 1
- WEAYCYAIVOIUMG-UHFFFAOYSA-N 1-methyl-4-(4-methylphenyl)sulfonylbenzene Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C1=CC=C(C)C=C1 WEAYCYAIVOIUMG-UHFFFAOYSA-N 0.000 description 1
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- GWQOQQVKVOOHTI-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxin-3-ylmethanol Chemical compound C1=CC=C2OC(CO)COC2=C1 GWQOQQVKVOOHTI-UHFFFAOYSA-N 0.000 description 1
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- UKHQUUMINBTTGU-UHFFFAOYSA-N bromo 4-methylbenzenesulfonate Chemical group CC1=CC=C(S(=O)(=O)OBr)C=C1 UKHQUUMINBTTGU-UHFFFAOYSA-N 0.000 description 1
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- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 1
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- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
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- 239000003085 diluting agent Substances 0.000 description 1
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- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- DEQYTNZJHKPYEZ-UHFFFAOYSA-N ethyl acetate;heptane Chemical compound CCOC(C)=O.CCCCCCC DEQYTNZJHKPYEZ-UHFFFAOYSA-N 0.000 description 1
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- XDRMBCMMABGNMM-UHFFFAOYSA-N ethyl benzenesulfonate Chemical compound CCOS(=O)(=O)C1=CC=CC=C1 XDRMBCMMABGNMM-UHFFFAOYSA-N 0.000 description 1
- AGNXHYCFWUFQIG-UHFFFAOYSA-N ethyl n-(2,2-dimethylpropanoyl)carbamate Chemical compound CCOC(=O)NC(=O)C(C)(C)C AGNXHYCFWUFQIG-UHFFFAOYSA-N 0.000 description 1
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- 230000012010 growth Effects 0.000 description 1
- 125000004969 haloethyl group Chemical group 0.000 description 1
- 125000004970 halomethyl group Chemical group 0.000 description 1
- RBBOWEDMXHTEPA-UHFFFAOYSA-N hexane;toluene Chemical compound CCCCCC.CC1=CC=CC=C1 RBBOWEDMXHTEPA-UHFFFAOYSA-N 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
- 125000001145 hydrido group Chemical group *[H] 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
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- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
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- 125000006431 methyl cyclopropyl group Chemical group 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
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- 235000010755 mineral Nutrition 0.000 description 1
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- 235000010446 mineral oil Nutrition 0.000 description 1
- AYOOGWWGECJQPI-NSHDSACASA-N n-[(1s)-1-(5-fluoropyrimidin-2-yl)ethyl]-3-(3-propan-2-yloxy-1h-pyrazol-5-yl)imidazo[4,5-b]pyridin-5-amine Chemical compound N1C(OC(C)C)=CC(N2C3=NC(N[C@@H](C)C=4N=CC(F)=CN=4)=CC=C3N=C2)=N1 AYOOGWWGECJQPI-NSHDSACASA-N 0.000 description 1
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- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- LMYJGUNNJIDROI-UHFFFAOYSA-N oxan-4-ol Chemical compound OC1CCOCC1 LMYJGUNNJIDROI-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 150000004031 phenylhydrazines Chemical class 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000001629 suppression Effects 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- YODQQARABJQLIP-UHFFFAOYSA-N thian-4-ol Chemical compound OC1CCSCC1 YODQQARABJQLIP-UHFFFAOYSA-N 0.000 description 1
- OVRJVKCZJCNSOW-UHFFFAOYSA-N thian-4-one Chemical compound O=C1CCSCC1 OVRJVKCZJCNSOW-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- BJYXNFYVCZIXQC-UHFFFAOYSA-N thiolan-3-ol Chemical compound OC1CCSC1 BJYXNFYVCZIXQC-UHFFFAOYSA-N 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
- 229940055764 triaz Drugs 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54159683A | 1983-10-13 | 1983-10-13 | |
| US541,596 | 1983-10-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1236463A true CA1236463A (en) | 1988-05-10 |
Family
ID=24160242
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000465372A Expired CA1236463A (en) | 1983-10-13 | 1984-10-12 | Herbicidal 1-aryl-.delta..sup.2-1,2,4-triazolin-5-ones |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0157876A1 (it) |
| AU (1) | AU3507784A (it) |
| CA (1) | CA1236463A (it) |
| IL (1) | IL73225A0 (it) |
| IT (1) | IT1196292B (it) |
| WO (1) | WO1985001637A1 (it) |
| ZA (1) | ZA848007B (it) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61501032A (ja) * | 1984-06-12 | 1986-05-22 | エフ エム シ− コ−ポレ−シヨン | 除草剤２↓−アリ−ル↓−１，２，４↓−トリアジン↓−３，５（２ｈ，４ｈ）↓−ジオン化合物及びその硫黄類似化合物 |
| BR8507017A (pt) * | 1984-10-31 | 1987-01-06 | Fmc Corp | Aril triazolinas herbicidas |
| JPS6299368A (ja) * | 1985-10-26 | 1987-05-08 | Nippon Nohyaku Co Ltd | Δ↑２−１，２，４−トリアゾリン−５−オン誘導体及びその製法並びにその用途 |
| US4845232A (en) * | 1985-10-26 | 1989-07-04 | Nihon Nohyaku Co., Ltd. | Process for producing 1,2,4-triazolin-5-one derivatives, and intermediates therefor |
| US4846875A (en) * | 1987-07-21 | 1989-07-11 | Fmc Corporation | Herbicidal triazolinones |
| DE3736297A1 (de) * | 1987-10-27 | 1989-05-11 | Basf Ag | N-phenyltetrahydrophthalimidverbindungen |
| JPH01249768A (ja) * | 1988-03-30 | 1989-10-05 | Nippon Tokushu Noyaku Seizo Kk | Ｎ−置換フエニル−ヘテロ環式化合物及び除草剤 |
| UA26918C2 (uk) | 1988-08-31 | 1999-12-29 | Фмк Корпорейшн | Похідhі триазоліhоhу, що проявляють гербіцидhу активhість, гербіцидhа композиція, спосіб придушеhhя росту бур'яhів |
| US4985065A (en) * | 1989-05-10 | 1991-01-15 | Fmc Corporation | Tetrazolinone herbicides |
| DE19802697A1 (de) * | 1998-01-24 | 1999-07-29 | Bayer Ag | Selektive Herbizide auf Basis von N-Aryl-triazolin(thi)onen und N-Arylsulfonylamino(thio)carbonyltriazolin(thi)onen |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4318731A (en) * | 1979-08-25 | 1982-03-09 | Nihon Nohyaku Co., Ltd. | Δ2 -1,2,4-triazolin-5-one derivatives and herbicidal usage thereof |
| US4404019A (en) * | 1980-12-24 | 1983-09-13 | Sumitomo Chemical Company, Limited | 3-Chloro-1-phenyl-1,2,4-triazolin-5-ones and their use as herbicides |
-
1984
- 1984-10-10 WO PCT/US1984/001638 patent/WO1985001637A1/en unknown
- 1984-10-10 EP EP84904023A patent/EP0157876A1/en not_active Withdrawn
- 1984-10-10 IL IL73225A patent/IL73225A0/xx unknown
- 1984-10-10 AU AU35077/84A patent/AU3507784A/en not_active Abandoned
- 1984-10-12 CA CA000465372A patent/CA1236463A/en not_active Expired
- 1984-10-12 ZA ZA848007A patent/ZA848007B/xx unknown
- 1984-10-12 IT IT23141/84A patent/IT1196292B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| AU3507784A (en) | 1985-05-07 |
| IT8423141A0 (it) | 1984-10-12 |
| WO1985001637A1 (en) | 1985-04-25 |
| IT8423141A1 (it) | 1986-04-12 |
| ZA848007B (en) | 1985-05-29 |
| IT1196292B (it) | 1988-11-16 |
| IL73225A0 (en) | 1985-01-31 |
| EP0157876A1 (en) | 1985-10-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry | ||
| MKEX | Expiry |
Effective date: 20050510 |