BG63123B1 - N-(1,2,4 триазолоазинил) бензенсулфонамидни и пиридинсул- фонамидни съединения и тяхното използванекато хербициди - Google Patents
N-(1,2,4 триазолоазинил) бензенсулфонамидни и пиридинсул- фонамидни съединения и тяхното използванекато хербициди Download PDFInfo
- Publication number
- BG63123B1 BG63123B1 BG102478A BG10247898A BG63123B1 BG 63123 B1 BG63123 B1 BG 63123B1 BG 102478 A BG102478 A BG 102478A BG 10247898 A BG10247898 A BG 10247898A BG 63123 B1 BG63123 B1 BG 63123B1
- Authority
- BG
- Bulgaria
- Prior art keywords
- alkyl
- methoxy
- chlorine
- trifluoromethyl
- och3
- Prior art date
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- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 239000004009 herbicide Substances 0.000 title abstract description 29
- -1 2-amino [1,2,4] triazole Chemical compound 0.000 claims abstract description 110
- CDRNYKLYADJTMN-UHFFFAOYSA-N pyridine-3-sulfonyl chloride Chemical class ClS(=O)(=O)C1=CC=CN=C1 CDRNYKLYADJTMN-UHFFFAOYSA-N 0.000 claims abstract description 7
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical class ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 claims abstract description 5
- NHAZGSRLKBTDBF-UHFFFAOYSA-N 1,2,4-triazol-1-amine Chemical class NN1C=NC=N1 NHAZGSRLKBTDBF-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 177
- 229910052739 hydrogen Inorganic materials 0.000 claims description 142
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 137
- 239000000460 chlorine Substances 0.000 claims description 95
- 239000000203 mixture Substances 0.000 claims description 89
- 229910052801 chlorine Inorganic materials 0.000 claims description 73
- 239000001257 hydrogen Substances 0.000 claims description 65
- 229910052799 carbon Inorganic materials 0.000 claims description 60
- 229910052757 nitrogen Inorganic materials 0.000 claims description 60
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 51
- 229910052794 bromium Inorganic materials 0.000 claims description 49
- 229910052731 fluorine Inorganic materials 0.000 claims description 44
- 229910052717 sulfur Inorganic materials 0.000 claims description 37
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 36
- 125000001424 substituent group Chemical group 0.000 claims description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
- 150000002431 hydrogen Chemical group 0.000 claims description 29
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 27
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 27
- 125000001153 fluoro group Chemical group F* 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- 239000011737 fluorine Substances 0.000 claims description 22
- 230000002363 herbicidal effect Effects 0.000 claims description 21
- 229910052740 iodine Inorganic materials 0.000 claims description 21
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 20
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- 239000000654 additive Substances 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
- SMBZJSVIKJMSFP-UHFFFAOYSA-N trifluoromethyl hypofluorite Chemical group FOC(F)(F)F SMBZJSVIKJMSFP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000004791 2-fluoroethoxy group Chemical group FCCO* 0.000 claims description 3
- 229910004013 NO 2 Inorganic materials 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 6
- 125000006012 2-chloroethoxy group Chemical group 0.000 claims 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 abstract description 11
- 125000004421 aryl sulphonamide group Chemical group 0.000 abstract description 9
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 abstract description 5
- LENLQGBLVGGAMF-UHFFFAOYSA-N tributyl([1,2,4]triazolo[1,5-a]pyridin-6-yl)stannane Chemical class C1=C([Sn](CCCC)(CCCC)CCCC)C=CC2=NC=NN21 LENLQGBLVGGAMF-UHFFFAOYSA-N 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 70
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
- 239000007787 solid Substances 0.000 description 56
- 239000000843 powder Substances 0.000 description 50
- 241000196324 Embryophyta Species 0.000 description 44
- 238000003756 stirring Methods 0.000 description 42
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 39
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 36
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 34
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
- 239000000428 dust Substances 0.000 description 33
- 238000001704 evaporation Methods 0.000 description 32
- 230000008020 evaporation Effects 0.000 description 32
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 238000002844 melting Methods 0.000 description 27
- 230000008018 melting Effects 0.000 description 27
- 238000000921 elemental analysis Methods 0.000 description 25
- 238000002360 preparation method Methods 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- 238000001914 filtration Methods 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 17
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 17
- 235000019341 magnesium sulphate Nutrition 0.000 description 17
- 239000003921 oil Substances 0.000 description 17
- 235000019198 oils Nutrition 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 238000001816 cooling Methods 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 150000002367 halogens Chemical group 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 9
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 239000000969 carrier Substances 0.000 description 8
- 229910052736 halogen Inorganic materials 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 239000011550 stock solution Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 240000007594 Oryza sativa Species 0.000 description 7
- 235000007164 Oryza sativa Nutrition 0.000 description 7
- 229960000583 acetic acid Drugs 0.000 description 7
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 7
- 235000009566 rice Nutrition 0.000 description 7
- 239000002689 soil Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 6
- 235000021307 Triticum Nutrition 0.000 description 6
- 241000209140 Triticum Species 0.000 description 6
- 238000007865 diluting Methods 0.000 description 6
- ALVPFGSHPUPROW-UHFFFAOYSA-N dipropyl disulfide Chemical compound CCCSSCCC ALVPFGSHPUPROW-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- DWJMBQYORXLGAE-UHFFFAOYSA-N pyridine-2-sulfonamide Chemical class NS(=O)(=O)C1=CC=CC=N1 DWJMBQYORXLGAE-UHFFFAOYSA-N 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 244000068988 Glycine max Species 0.000 description 5
- 235000010469 Glycine max Nutrition 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 150000008331 benzenesulfonamides Chemical class 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical class Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 5
- 230000006378 damage Effects 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Inorganic materials [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- DPZNOMCNRMUKPS-UHFFFAOYSA-N 1,3-Dimethoxybenzene Chemical compound COC1=CC=CC(OC)=C1 DPZNOMCNRMUKPS-UHFFFAOYSA-N 0.000 description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- DBJPBHJHAPAUQU-UHFFFAOYSA-N 5,8-dimethoxy-[1,2,4]triazolo[1,5-c]pyrimidin-2-amine Chemical compound COC1=CN=C(OC)N2N=C(N)N=C12 DBJPBHJHAPAUQU-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 239000004927 clay Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 230000018109 developmental process Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 4
- WJJBIYLGJUVNJX-UHFFFAOYSA-N pyrimidine-2-sulfonamide Chemical class NS(=O)(=O)C1=NC=CC=N1 WJJBIYLGJUVNJX-UHFFFAOYSA-N 0.000 description 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 4
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 description 3
- TZFDIWVKNFJGDH-UHFFFAOYSA-N 1-benzylsulfanyl-2-methoxybenzene Chemical compound COC1=CC=CC=C1SCC1=CC=CC=C1 TZFDIWVKNFJGDH-UHFFFAOYSA-N 0.000 description 3
- KLVZDQNSNTUNGU-UHFFFAOYSA-N 2,6-dimethoxybenzenesulfonyl chloride Chemical compound COC1=CC=CC(OC)=C1S(Cl)(=O)=O KLVZDQNSNTUNGU-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- DMKFWTCEKLNOKK-UHFFFAOYSA-N 2-methoxy-4-(trifluoromethyl)pyridine-3-sulfonyl chloride Chemical compound COC1=NC=CC(C(F)(F)F)=C1S(Cl)(=O)=O DMKFWTCEKLNOKK-UHFFFAOYSA-N 0.000 description 3
- BJYNYQGJTZULJI-UHFFFAOYSA-N 2-methoxy-5-methylbenzenesulfonyl chloride Chemical compound COC1=CC=C(C)C=C1S(Cl)(=O)=O BJYNYQGJTZULJI-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 240000002791 Brassica napus Species 0.000 description 3
- 235000006008 Brassica napus var napus Nutrition 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 3
- 244000299507 Gossypium hirsutum Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
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- 239000000284 extract Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- HMJLICZVJHBGIN-UHFFFAOYSA-N methyl 2-chlorosulfonyl-3-methoxybenzoate Chemical compound COC(=O)C1=CC=CC(OC)=C1S(Cl)(=O)=O HMJLICZVJHBGIN-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229940124530 sulfonamide Drugs 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- RBWNDVYFFBLMPZ-UHFFFAOYSA-N 1-methoxy-2-propylsulfanyl-3-(trifluoromethyl)benzene Chemical compound CCCSC1=C(OC)C=CC=C1C(F)(F)F RBWNDVYFFBLMPZ-UHFFFAOYSA-N 0.000 description 2
- BJGPIZPEUCJKHY-UHFFFAOYSA-N 2-(1,1,2,2-tetrafluoroethoxy)benzenesulfonyl chloride Chemical compound FC(F)C(F)(F)OC1=CC=CC=C1S(Cl)(=O)=O BJGPIZPEUCJKHY-UHFFFAOYSA-N 0.000 description 2
- MUHLBQUPTQLQLQ-UHFFFAOYSA-N 2-methoxy-1-propylsulfanyl-4-(trifluoromethyl)benzene Chemical compound CCCSC1=CC=C(C(F)(F)F)C=C1OC MUHLBQUPTQLQLQ-UHFFFAOYSA-N 0.000 description 2
- TXBYWRCAEYSVFA-UHFFFAOYSA-N 2-methoxy-3-propylsulfanyl-4-(trifluoromethyl)pyridine Chemical compound CCCSC1=C(OC)N=CC=C1C(F)(F)F TXBYWRCAEYSVFA-UHFFFAOYSA-N 0.000 description 2
- NBZJAHPYJUXLQC-UHFFFAOYSA-N 2-methoxy-6-(trifluoromethyl)benzenesulfonyl chloride Chemical compound COC1=CC=CC(C(F)(F)F)=C1S(Cl)(=O)=O NBZJAHPYJUXLQC-UHFFFAOYSA-N 0.000 description 2
- RINPFKDQCWLBEK-UHFFFAOYSA-N 3-methoxy-2-propylsulfanylbenzoic acid Chemical compound CCCSC1=C(OC)C=CC=C1C(O)=O RINPFKDQCWLBEK-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- QYQKVLHYWFIURN-UHFFFAOYSA-N 8-chloro-5-methoxy-[1,2,4]triazolo[1,5-c]pyrimidin-2-amine Chemical compound COC1=NC=C(Cl)C2=NC(N)=NN12 QYQKVLHYWFIURN-UHFFFAOYSA-N 0.000 description 2
- KIKWOPRYZVFPSB-UHFFFAOYSA-N 8-chloro-5-methoxy-n-trimethylsilyl-[1,2,4]triazolo[1,5-c]pyrimidin-2-amine Chemical compound COC1=NC=C(Cl)C2=NC(N[Si](C)(C)C)=NN12 KIKWOPRYZVFPSB-UHFFFAOYSA-N 0.000 description 2
- XWEXEGOUNWGVJC-UHFFFAOYSA-N 8-chloro-5-methylsulfanyl-[1,2,4]triazolo[4,3-c]pyrimidin-3-amine;hydrobromide Chemical compound Br.CSC1=NC=C(Cl)C2=NN=C(N)N12 XWEXEGOUNWGVJC-UHFFFAOYSA-N 0.000 description 2
- 241001621841 Alopecurus myosuroides Species 0.000 description 2
- 235000007320 Avena fatua Nutrition 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- 125000006519 CCH3 Chemical group 0.000 description 2
- 101100234822 Caenorhabditis elegans ltd-1 gene Proteins 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- 238000005917 acylation reaction Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- ICSNLGPSRYBMBD-UHFFFAOYSA-N alpha-aminopyridine Natural products NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzidamine Natural products C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 description 1
- MKQSWTQPLLCSOB-UHFFFAOYSA-N benzyl 2-chloro-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate Chemical compound N1=C(Cl)SC(C(=O)OCC=2C=CC=CC=2)=C1C(F)(F)F MKQSWTQPLLCSOB-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- LKMCJXXOBRCATQ-UHFFFAOYSA-N benzylsulfanylbenzene Chemical class C=1C=CC=CC=1CSC1=CC=CC=C1 LKMCJXXOBRCATQ-UHFFFAOYSA-N 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 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
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- RIUXZHMCCFLRBI-UHFFFAOYSA-N chlorimuron Chemical compound COC1=CC(Cl)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 RIUXZHMCCFLRBI-UHFFFAOYSA-N 0.000 description 1
- 125000006011 chloroethoxy group Chemical group 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- KIEDNEWSYUYDSN-UHFFFAOYSA-N clomazone Chemical compound O=C1C(C)(C)CON1CC1=CC=CC=C1Cl KIEDNEWSYUYDSN-UHFFFAOYSA-N 0.000 description 1
- HUBANNPOLNYSAD-UHFFFAOYSA-N clopyralid Chemical compound OC(=O)C1=NC(Cl)=CC=C1Cl HUBANNPOLNYSAD-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 229940125878 compound 36 Drugs 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- HBGGBCVEFUPUNY-UHFFFAOYSA-N cyclododecanamine Chemical compound NC1CCCCCCCCCCC1 HBGGBCVEFUPUNY-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- YDVNLQGCLLPHAH-UHFFFAOYSA-N dichloromethane;hydrate Chemical compound O.ClCCl YDVNLQGCLLPHAH-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- BWUPSGJXXPATLU-UHFFFAOYSA-N dimepiperate Chemical compound C=1C=CC=CC=1C(C)(C)SC(=O)N1CCCCC1 BWUPSGJXXPATLU-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical class CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- BDTDECDAHYOJRO-UHFFFAOYSA-N ethyl n-(sulfanylidenemethylidene)carbamate Chemical compound CCOC(=O)N=C=S BDTDECDAHYOJRO-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- RZILCCPWPBTYDO-UHFFFAOYSA-N fluometuron Chemical compound CN(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 RZILCCPWPBTYDO-UHFFFAOYSA-N 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 229910003472 fullerene Inorganic materials 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 238000010353 genetic engineering Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229940100242 glycol stearate Drugs 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- CONWAEURSVPLRM-UHFFFAOYSA-N lactofen Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC(C)C(=O)OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 CONWAEURSVPLRM-UHFFFAOYSA-N 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- JDOZOOBCADNBIJ-UHFFFAOYSA-N lithium;2h-pyridin-2-ide Chemical compound [Li+].C1=CC=N[C-]=C1 JDOZOOBCADNBIJ-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- OBUVUJFTXIJWSX-UHFFFAOYSA-N methyl 3-methoxy-2-propylsulfanylbenzoate Chemical compound CCCSC1=C(OC)C=CC=C1C(=O)OC OBUVUJFTXIJWSX-UHFFFAOYSA-N 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- FDEUKEQHTSJLTA-UHFFFAOYSA-N n-([1,2,4]triazolo[1,5-a]pyridin-2-yl)benzenesulfonamide Chemical compound N1=C2C=CC=CN2N=C1NS(=O)(=O)C1=CC=CC=C1 FDEUKEQHTSJLTA-UHFFFAOYSA-N 0.000 description 1
- DHAPBBUXEDAFAU-UHFFFAOYSA-N n-([1,2,4]triazolo[1,5-a]pyridin-2-yl)pyridine-3-sulfonamide Chemical class N1=C2C=CC=CN2N=C1NS(=O)(=O)C1=CC=CN=C1 DHAPBBUXEDAFAU-UHFFFAOYSA-N 0.000 description 1
- WRBXZOZOTBCPAG-UHFFFAOYSA-N n-([1,2,4]triazolo[1,5-a]pyrimidin-2-yl)benzenesulfonamide Chemical class N1=C2N=CC=CN2N=C1NS(=O)(=O)C1=CC=CC=C1 WRBXZOZOTBCPAG-UHFFFAOYSA-N 0.000 description 1
- SRSPKOVFMZHHDV-UHFFFAOYSA-N n-([1,2,4]triazolo[1,5-c]pyrimidin-2-yl)benzenesulfonamide Chemical class N1=C2C=CN=CN2N=C1NS(=O)(=O)C1=CC=CC=C1 SRSPKOVFMZHHDV-UHFFFAOYSA-N 0.000 description 1
- 238000002663 nebulization Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- RAASNKWPYCKKLW-UHFFFAOYSA-N o-methyl 3-methoxy-2-propylbenzenecarbothioate Chemical compound CCCC1=C(OC)C=CC=C1C(=S)OC RAASNKWPYCKKLW-UHFFFAOYSA-N 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- HJMNOOURRPJWCF-UHFFFAOYSA-N propoxysulfinyl propyl sulfite Chemical compound S(=O)(OCCC)OS(=O)OCCC HJMNOOURRPJWCF-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- JQJOGAGLBDBMLU-UHFFFAOYSA-N pyridine-2-sulfonyl chloride Chemical class ClS(=O)(=O)C1=CC=CC=N1 JQJOGAGLBDBMLU-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000723 toxicological property Toxicity 0.000 description 1
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PNQBEPDZQUOCNY-UHFFFAOYSA-N trifluoroacetyl chloride Chemical compound FC(F)(F)C(Cl)=O PNQBEPDZQUOCNY-UHFFFAOYSA-N 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D333/66—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US2655696P | 1996-09-24 | 1996-09-24 | |
PCT/US1997/016867 WO1998013367A1 (en) | 1996-09-24 | 1997-09-23 | N-([1,2,4] triazoloazinyl)benzenesulfonamide and pyridinesulfonamide compounds and their use as herbicides |
Publications (2)
Publication Number | Publication Date |
---|---|
BG102478A BG102478A (en) | 1999-08-31 |
BG63123B1 true BG63123B1 (bg) | 2001-04-30 |
Family
ID=21832490
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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BG102478A BG63123B1 (bg) | 1996-09-24 | 1998-05-22 | N-(1,2,4 триазолоазинил) бензенсулфонамидни и пиридинсул- фонамидни съединения и тяхното използванекато хербициди |
Country Status (23)
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US (5) | US5858924A (es) |
EP (1) | EP0877745B1 (es) |
JP (2) | JP4215824B2 (es) |
KR (1) | KR100488277B1 (es) |
CN (2) | CN1159297C (es) |
AR (1) | AR012020A1 (es) |
AU (1) | AU723666B2 (es) |
BG (1) | BG63123B1 (es) |
BR (1) | BR9706774B1 (es) |
CA (1) | CA2238316C (es) |
CO (1) | CO4900002A1 (es) |
CZ (1) | CZ297521B6 (es) |
DE (2) | DE69705821T2 (es) |
DK (1) | DK0877745T3 (es) |
EA (1) | EA001064B1 (es) |
ES (1) | ES2158513T3 (es) |
FR (1) | FR08C0037I2 (es) |
GR (1) | GR3036961T3 (es) |
HU (2) | HU229886B1 (es) |
PL (1) | PL190282B1 (es) |
TR (1) | TR199800906T1 (es) |
UA (1) | UA59350C2 (es) |
WO (1) | WO1998013367A1 (es) |
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AR035209A1 (es) | 2000-11-03 | 2004-05-05 | Dow Agrosciences Llc | Compuestos de n-(5,7-dimetoxi(1,2,4)triazol(1,5-a)pirimidin-2-il)arilsulfonamida y composiciones herbicidas formuladas con dichos compuestos como agente activo; proceso para prepararlos y metodo para controlar vegetacion indeseable utilizando dichos compuestos |
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CN107668053A (zh) * | 2017-11-27 | 2018-02-09 | 浙江永太科技股份有限公司 | 一种含哒草特和五氟磺草胺的除草剂组合物 |
CN108395435B (zh) * | 2018-05-10 | 2021-02-05 | 深圳大学 | 三唑并嘧啶磺酰胺类化合物及其制备方法和应用 |
CN108558744A (zh) * | 2018-07-04 | 2018-09-21 | 常州大学 | 一种2-甲氧基-4-三氟甲基-3-吡啶磺酰氯的制备方法 |
CN108707109A (zh) * | 2018-08-29 | 2018-10-26 | 常州沃腾化工科技有限公司 | 一种2-甲氧基-4-三氟甲基吡啶-3-磺酰氯的制备方法 |
CN113227052A (zh) * | 2018-12-27 | 2021-08-06 | 科迪华农业科技有限责任公司 | 磺酰胺除草剂方法中间体的制备 |
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1997
- 1997-09-23 PL PL97327108A patent/PL190282B1/pl unknown
- 1997-09-23 AR ARP970104360A patent/AR012020A1/es active IP Right Grant
- 1997-09-23 EA EA199800478A patent/EA001064B1/ru not_active IP Right Cessation
- 1997-09-23 ES ES97909857T patent/ES2158513T3/es not_active Expired - Lifetime
- 1997-09-23 HU HU1200420A patent/HU229886B1/hu unknown
- 1997-09-23 DE DE69705821T patent/DE69705821T2/de not_active Expired - Lifetime
- 1997-09-23 DE DE122009000052C patent/DE122009000052I2/de active Active
- 1997-09-23 CN CNB02118609XA patent/CN1159297C/zh not_active Expired - Lifetime
- 1997-09-23 TR TR1998/00906T patent/TR199800906T1/xx unknown
- 1997-09-23 CZ CZ0156398A patent/CZ297521B6/cs not_active IP Right Cessation
- 1997-09-23 WO PCT/US1997/016867 patent/WO1998013367A1/en active IP Right Grant
- 1997-09-23 CA CA002238316A patent/CA2238316C/en not_active Expired - Lifetime
- 1997-09-23 BR BRPI9706774-1A patent/BR9706774B1/pt not_active IP Right Cessation
- 1997-09-23 DK DK97909857T patent/DK0877745T3/da active
- 1997-09-23 AU AU47363/97A patent/AU723666B2/en not_active Expired
- 1997-09-23 KR KR10-1998-0703833A patent/KR100488277B1/ko not_active IP Right Cessation
- 1997-09-23 US US08/936,046 patent/US5858924A/en not_active Expired - Lifetime
- 1997-09-23 UA UA98052683A patent/UA59350C2/uk unknown
- 1997-09-23 CN CN97191491A patent/CN1092195C/zh not_active Expired - Lifetime
- 1997-09-23 JP JP51578798A patent/JP4215824B2/ja not_active Expired - Lifetime
- 1997-09-23 HU HU0002072A patent/HU228039B1/hu unknown
- 1997-09-23 EP EP97909857A patent/EP0877745B1/en not_active Expired - Lifetime
- 1997-09-24 CO CO97055758A patent/CO4900002A1/es unknown
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1998
- 1998-05-22 BG BG102478A patent/BG63123B1/bg unknown
- 1998-07-31 US US09/127,378 patent/US6130335A/en not_active Expired - Lifetime
- 1998-07-31 US US09/127,328 patent/US6005108A/en not_active Expired - Lifetime
- 1998-07-31 US US09/127,384 patent/US5965490A/en not_active Expired - Lifetime
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2000
- 2000-03-16 US US09/527,857 patent/US6303814B1/en not_active Expired - Lifetime
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2008
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- 2008-09-10 FR FR08C0037C patent/FR08C0037I2/fr active Active
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