SK51998A3 - Herbicidal sulfonamides - Google Patents
Herbicidal sulfonamides Download PDFInfo
- Publication number
- SK51998A3 SK51998A3 SK519-98A SK51998A SK51998A3 SK 51998 A3 SK51998 A3 SK 51998A3 SK 51998 A SK51998 A SK 51998A SK 51998 A3 SK51998 A3 SK 51998A3
- Authority
- SK
- Slovakia
- Prior art keywords
- chf
- chcl
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- 230000002363 herbicidal effect Effects 0.000 title claims description 7
- 229940124530 sulfonamide Drugs 0.000 title description 10
- 150000003456 sulfonamides Chemical class 0.000 title description 9
- 239000000460 chlorine Chemical group 0.000 claims description 2953
- 150000001875 compounds Chemical class 0.000 claims description 195
- -1 alkoxyalkyl carbon Chemical compound 0.000 claims description 75
- 229910052739 hydrogen Inorganic materials 0.000 claims description 61
- 125000004432 carbon atom Chemical group C* 0.000 claims description 60
- 239000000203 mixture Substances 0.000 claims description 60
- 239000001257 hydrogen Substances 0.000 claims description 55
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 36
- 239000005562 Glyphosate Substances 0.000 claims description 34
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 33
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 28
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims description 28
- 229940097068 glyphosate Drugs 0.000 claims description 28
- 125000001153 fluoro group Chemical group F* 0.000 claims description 25
- 125000005843 halogen group Chemical group 0.000 claims description 23
- 229910052731 fluorine Inorganic materials 0.000 claims description 22
- 229910052760 oxygen Inorganic materials 0.000 claims description 22
- 229910052801 chlorine Chemical group 0.000 claims description 21
- 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 claims description 21
- 239000005586 Nicosulfuron Substances 0.000 claims description 20
- 239000005604 Prosulfuron Substances 0.000 claims description 20
- LTUNNEGNEKBSEH-UHFFFAOYSA-N Prosulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)CCC(F)(F)F)=N1 LTUNNEGNEKBSEH-UHFFFAOYSA-N 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 18
- 239000011737 fluorine Chemical group 0.000 claims description 18
- 239000007787 solid Substances 0.000 claims description 18
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 17
- NSWAMPCUPHPTTC-UHFFFAOYSA-N chlorimuron-ethyl Chemical group CCOC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(Cl)=CC(OC)=N1 NSWAMPCUPHPTTC-UHFFFAOYSA-N 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 239000004094 surface-active agent Substances 0.000 claims description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 13
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 12
- 239000005574 MCPA Substances 0.000 claims description 12
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 claims description 12
- 125000001188 haloalkyl group Chemical group 0.000 claims description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 11
- 239000005558 Fluroxypyr Substances 0.000 claims description 11
- VJYIFXVZLXQVHO-UHFFFAOYSA-N chlorsulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)Cl)=N1 VJYIFXVZLXQVHO-UHFFFAOYSA-N 0.000 claims description 11
- MEFQWPUMEMWTJP-UHFFFAOYSA-N fluroxypyr Chemical compound NC1=C(Cl)C(F)=NC(OCC(O)=O)=C1Cl MEFQWPUMEMWTJP-UHFFFAOYSA-N 0.000 claims description 11
- MPPOHAUSNPTFAJ-UHFFFAOYSA-N 2-[4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 MPPOHAUSNPTFAJ-UHFFFAOYSA-N 0.000 claims description 10
- 239000005606 Pyridate Substances 0.000 claims description 10
- JTZCTMAVMHRNTR-UHFFFAOYSA-N Pyridate Chemical compound CCCCCCCCSC(=O)OC1=CC(Cl)=NN=C1C1=CC=CC=C1 JTZCTMAVMHRNTR-UHFFFAOYSA-N 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 10
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 9
- HKELWJONQIFBPO-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-5-(trichloromethyl)-1,2,4-triazole-3-carboxylic acid Chemical compound N1=C(C(=O)O)N=C(C(Cl)(Cl)Cl)N1C1=CC=C(Cl)C=C1Cl HKELWJONQIFBPO-UHFFFAOYSA-N 0.000 claims description 9
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 claims description 9
- CABMTIJINOIHOD-UHFFFAOYSA-N 2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]quinoline-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC2=CC=CC=C2C=C1C(O)=O CABMTIJINOIHOD-UHFFFAOYSA-N 0.000 claims description 9
- 239000005981 Imazaquin Substances 0.000 claims description 9
- 239000005624 Tralkoxydim Substances 0.000 claims description 9
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 9
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 claims description 9
- 239000005618 Sulcotrione Substances 0.000 claims description 8
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 8
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 8
- 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 claims description 8
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- PQTBTIFWAXVEPB-UHFFFAOYSA-N sulcotrione Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O PQTBTIFWAXVEPB-UHFFFAOYSA-N 0.000 claims description 8
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
- RBSXHDIPCIWOMG-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-3-(2-ethylsulfonylimidazo[1,2-a]pyridin-3-yl)sulfonylurea Chemical compound CCS(=O)(=O)C=1N=C2C=CC=CN2C=1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 RBSXHDIPCIWOMG-UHFFFAOYSA-N 0.000 claims description 7
- GOCUAJYOYBLQRH-UHFFFAOYSA-N 2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl GOCUAJYOYBLQRH-UHFFFAOYSA-N 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000005619 Sulfosulfuron Substances 0.000 claims description 7
- 239000005625 Tri-allate Substances 0.000 claims description 7
- 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 claims description 7
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 7
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 claims description 7
- LBGPXIPGGRQBJW-UHFFFAOYSA-N Difenzoquat Chemical compound C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 LBGPXIPGGRQBJW-UHFFFAOYSA-N 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 230000012010 growth Effects 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- 239000011734 sodium Substances 0.000 claims description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- VAIZTNZGPYBOGF-CYBMUJFWSA-N fluazifop-P-butyl Chemical group C1=CC(O[C@H](C)C(=O)OCCCC)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 VAIZTNZGPYBOGF-CYBMUJFWSA-N 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 239000005621 Terbuthylazine Substances 0.000 claims description 4
- 150000001721 carbon Chemical class 0.000 claims description 4
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 4
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 4
- COYBRKAVBMYYSF-UHFFFAOYSA-N heptan-2-yl [(5-chloroquinolin-8-yl)oxy]acetate Chemical group C1=CN=C2C(OCC(=O)OC(C)CCCCC)=CC=C(Cl)C2=C1 COYBRKAVBMYYSF-UHFFFAOYSA-N 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 claims description 4
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 claims description 3
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 claims description 3
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- JLYFCTQDENRSOL-UHFFFAOYSA-N 2-chloro-N-(2,4-dimethylthiophen-3-yl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound COCC(C)N(C(=O)CCl)C=1C(C)=CSC=1C JLYFCTQDENRSOL-UHFFFAOYSA-N 0.000 claims description 2
- WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 claims description 2
- DXBQEHHOGRVYFF-UHFFFAOYSA-N 3-pyridin-4-ylpentane-2,4-dione Chemical group CC(=O)C(C(C)=O)C1=CC=NC=C1 DXBQEHHOGRVYFF-UHFFFAOYSA-N 0.000 claims description 2
- 239000005476 Bentazone Substances 0.000 claims description 2
- RRVIAQKBTUQODI-UHFFFAOYSA-N Methabenzthiazuron Chemical compound C1=CC=C2SC(N(C)C(=O)NC)=NC2=C1 RRVIAQKBTUQODI-UHFFFAOYSA-N 0.000 claims description 2
- 239000005582 Metosulam Substances 0.000 claims description 2
- VGHPMIFEKOFHHQ-UHFFFAOYSA-N Metosulam Chemical compound N1=C2N=C(OC)C=C(OC)N2N=C1S(=O)(=O)NC1=C(Cl)C=CC(C)=C1Cl VGHPMIFEKOFHHQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000005603 Prosulfocarb Substances 0.000 claims description 2
- 125000004702 alkoxy alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzidamine Natural products C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 2
- 125000004461 halocycloalkylalkyl group Chemical group 0.000 claims description 2
- PUIYMUZLKQOUOZ-UHFFFAOYSA-N isoproturon Chemical compound CC(C)C1=CC=C(NC(=O)N(C)C)C=C1 PUIYMUZLKQOUOZ-UHFFFAOYSA-N 0.000 claims description 2
- DSRNRYQBBJQVCW-UHFFFAOYSA-N metoxuron Chemical compound COC1=CC=C(NC(=O)N(C)C)C=C1Cl DSRNRYQBBJQVCW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000466 oxiranyl group Chemical group 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 claims description 2
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 claims description 2
- QICWSAFHNDKQKS-UHFFFAOYSA-N sodium;methylsulfonylazanide Chemical compound [Na+].CS([NH-])(=O)=O QICWSAFHNDKQKS-UHFFFAOYSA-N 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- PVSGXWMWNRGTKE-UHFFFAOYSA-N 5-methyl-2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]pyridine-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC=C(C)C=C1C(O)=O PVSGXWMWNRGTKE-UHFFFAOYSA-N 0.000 claims 1
- LXKOADMMGWXPJQ-UHFFFAOYSA-N Halosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N(N=C(Cl)C=2C(O)=O)C)=N1 LXKOADMMGWXPJQ-UHFFFAOYSA-N 0.000 claims 1
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- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 125000005203 haloalkylcarbonyloxy group Chemical group 0.000 claims 1
- IOXAXYHXMLCCJJ-UHFFFAOYSA-N oxetan-3-yl 2-[(4,6-dimethylpyrimidin-2-yl)carbamoylsulfamoyl]benzoate Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(=O)OC2COC2)=N1 IOXAXYHXMLCCJJ-UHFFFAOYSA-N 0.000 claims 1
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- 150000003457 sulfones Chemical class 0.000 claims 1
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- AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 description 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
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- CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 description 1
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- 230000003389 potentiating effect Effects 0.000 description 1
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- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 description 1
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- PHNUZKMIPFFYSO-UHFFFAOYSA-N propyzamide Chemical compound C#CC(C)(C)NC(=O)C1=CC(Cl)=CC(Cl)=C1 PHNUZKMIPFFYSO-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
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- ASRAWSBMDXVNLX-UHFFFAOYSA-N pyrazolynate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OS(=O)(=O)C1=CC=C(C)C=C1 ASRAWSBMDXVNLX-UHFFFAOYSA-N 0.000 description 1
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- 238000010791 quenching Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
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- 238000000926 separation method Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
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- 239000011780 sodium chloride Substances 0.000 description 1
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- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- PDEFQWNXOUGDJR-UHFFFAOYSA-M sodium;2,2-dichloropropanoate Chemical compound [Na+].CC(Cl)(Cl)C([O-])=O PDEFQWNXOUGDJR-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
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- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- OORLZFUTLGXMEF-UHFFFAOYSA-N sulfentrazone Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(NS(C)(=O)=O)=C(Cl)C=C1Cl OORLZFUTLGXMEF-UHFFFAOYSA-N 0.000 description 1
- ZDXMLEQEMNLCQG-UHFFFAOYSA-N sulfometuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 ZDXMLEQEMNLCQG-UHFFFAOYSA-N 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
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- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- LOQQVLXUKHKNIA-UHFFFAOYSA-N thifensulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C2=C(SC=C2)C(O)=O)=N1 LOQQVLXUKHKNIA-UHFFFAOYSA-N 0.000 description 1
- 210000003371 toe Anatomy 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- 125000001874 trioxidanyl group Chemical group [*]OOO[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; Derivatives thereof
- A01N41/06—Sulfonic acid amides
-
- 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
-
- 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
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/42—One nitrogen atom
- C07D251/46—One nitrogen atom with oxygen or sulfur atoms attached to the two other ring carbon atoms
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US703195P | 1995-10-25 | 1995-10-25 | |
| US1232996P | 1996-02-27 | 1996-02-27 | |
| PCT/US1996/016111 WO1997015576A1 (en) | 1995-10-25 | 1996-10-08 | Herbicidal sulfonamides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK51998A3 true SK51998A3 (en) | 1998-09-09 |
Family
ID=26676376
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK519-98A SK51998A3 (en) | 1995-10-25 | 1996-10-08 | Herbicidal sulfonamides |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US6060432A (cs) |
| EP (1) | EP0862571B1 (cs) |
| JP (1) | JPH11514370A (cs) |
| KR (1) | KR19990067047A (cs) |
| CN (1) | CN1202172A (cs) |
| AR (1) | AR004082A1 (cs) |
| AT (1) | ATE231151T1 (cs) |
| AU (1) | AU712362B2 (cs) |
| BR (1) | BR9611133A (cs) |
| CA (1) | CA2235146C (cs) |
| CZ (1) | CZ121298A3 (cs) |
| DE (1) | DE69625825T2 (cs) |
| DK (1) | DK0862571T3 (cs) |
| ES (1) | ES2191117T3 (cs) |
| HU (1) | HUP9802363A3 (cs) |
| IL (1) | IL124158A (cs) |
| PL (1) | PL328095A1 (cs) |
| SK (1) | SK51998A3 (cs) |
| TR (1) | TR199800718T2 (cs) |
| TW (1) | TW357053B (cs) |
| WO (1) | WO1997015576A1 (cs) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA981168B (en) | 1997-02-19 | 1999-08-12 | Du Pont | Compounds and processes for making herbicidal sulfonamides. |
| DE19731784A1 (de) * | 1997-07-24 | 1999-02-04 | Bayer Ag | Substituierte N-Aryl-N-thioxocarbonyl-sulfonamide |
| US6395767B2 (en) | 2000-03-10 | 2002-05-28 | Bristol-Myers Squibb Company | Cyclopropyl-fused pyrrolidine-based inhibitors of dipeptidyl peptidase IV and method |
| US7214825B2 (en) * | 2003-10-17 | 2007-05-08 | Honeywell International Inc. | O-(3-chloropropenyl) hydroxylamine free base |
| CA2558642C (en) | 2004-03-10 | 2017-08-08 | Monsanto Technology Llc | Herbicidal compositions containing n-phosphonomethyl glycine and an auxin herbicide |
| BRPI0519288A2 (pt) | 2004-12-24 | 2009-01-06 | Astrazeneca Ab | compostos heterocÍclicos como antagonistas de ccr2b |
| RU2488270C2 (ru) * | 2008-02-05 | 2013-07-27 | Ариста Лайфсайенс Норс Америка, Ллс | Твердый состав легкоплавкого активного соединения |
| US20120142532A1 (en) | 2009-08-10 | 2012-06-07 | Monsanto Technology Llc | Low volatility auxin herbicide formulations |
| UY39627A (es) | 2011-10-26 | 2022-03-31 | Monsanto Technology Llc | Sales de herbicidas de ácido carboxílico |
| JP6162146B2 (ja) * | 2012-01-12 | 2017-07-12 | ダウ アグロサイエンシィズ エルエルシー | ベンタゾンとals阻害剤とaccアーゼ阻害剤とを含有する除草剤組成物 |
| WO2013184622A2 (en) | 2012-06-04 | 2013-12-12 | Monsanto Technology Llc | Aqueous concentrated herbicidal compositions containing glyphosate salts and dicamba salts |
| CN110495471A (zh) | 2013-02-27 | 2019-11-26 | 孟山都技术公司 | 用于具有改进的挥发性的麦草畏桶混合物的草甘膦组合物 |
| WO2017041230A1 (en) * | 2015-09-08 | 2017-03-16 | Aceneobiochem, Inc. | Herbicidal chloromethyl triazolinones |
| KR20180080286A (ko) | 2015-11-05 | 2018-07-11 | 바스프 에스이 | 식물병원성 진균 퇴치용 치환된 옥사디아졸 |
| US10492494B2 (en) | 2015-11-13 | 2019-12-03 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
| AR106679A1 (es) | 2015-11-13 | 2018-02-07 | Basf Se | Oxadiazoles sustituidos para combatir hongos fitopatógenos |
| CA3003949A1 (en) | 2015-11-19 | 2017-05-26 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
| WO2017085098A1 (en) | 2015-11-19 | 2017-05-26 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
| CN105284796A (zh) * | 2015-11-20 | 2016-02-03 | 佛山市盈辉作物科学有限公司 | 除草剂添加剂、含除草剂添加剂的除草组合物及生产设备 |
| AU2017250397A1 (en) | 2016-04-11 | 2018-10-11 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
| RU2018146743A (ru) | 2016-06-09 | 2020-07-09 | Басф Се | Замещенные оксадиазолы для борьбы с фитопатогенными грибами |
| US20210368793A1 (en) | 2016-08-05 | 2021-12-02 | Basf Se | Method for Controlling PPO Resistant Weeds |
| WO2018080859A1 (en) | 2016-10-24 | 2018-05-03 | E. I. Du Pont De Nemours And Company | Fungicidal oxadiazoles |
| TW202220953A (zh) * | 2020-07-29 | 2022-06-01 | 美商富曼西公司 | 經取代的鹵代烷基磺胺類除草劑 |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0077938A3 (en) * | 1981-10-23 | 1983-08-24 | Mitsubishi Kasei Corporation | N-(3-substituted aminophenyl) tetrahydrophthalimides and herbicidal composition |
| US4666507A (en) * | 1985-01-16 | 1987-05-19 | Nippon Kayaku Kabushiki Kaisha | Herbicidal 5-halo-1-[5-(N-substituted sulfonylamino)phenyl]pyrazole derivatives |
| CN85106905A (zh) * | 1985-08-08 | 1987-02-04 | Fmc公司 | 含有1-芳基-δ2-1,2,4,-三唑啉-5-酮类的除草剂及其制备方法 |
| US5041155A (en) * | 1989-04-03 | 1991-08-20 | Fmc Corporation | Herbicidal aryl triazolinones |
| DE3813884A1 (de) * | 1988-04-20 | 1989-11-16 | Schering Ag | Substituierte 1-oxo-3-thioxo-2,3,5,8-tetrahydro-1h- (1,2,4)-triazolo(1,2-(alpha))pyridazine, verfahren zu ihrer herstellung und ihre verwendung als mittel mit herbizider wirkung |
| DE3835168A1 (de) * | 1988-10-15 | 1990-04-19 | Bayer Ag | N-aryl-stickstoffheterocyclen, mehrere verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| JP3089621B2 (ja) * | 1990-12-17 | 2000-09-18 | 日産化学工業株式会社 | ウラシル誘導体 |
| DE69228707T2 (de) * | 1992-01-29 | 1999-10-21 | E.I. Du Pont De Nemours And Co., Wilmington | Substituierte phenylheterozyklische herbizide |
| WO1994003454A1 (en) * | 1992-07-29 | 1994-02-17 | E.I. Du Pont De Nemours And Company | Herbicidal triazinones |
| DE4225629A1 (de) * | 1992-07-30 | 1994-02-03 | Degussa | Heterocyclische Verbindungen |
| WO1994004511A1 (en) * | 1992-08-21 | 1994-03-03 | Nissan Chemical Industries, Ltd. | Pyrimidine derivative and weedkiller |
| DE9321642U1 (de) * | 1992-09-10 | 2001-11-08 | Degussa AG, 40474 Düsseldorf | Bizyklische Imide |
| DE4236220A1 (de) * | 1992-10-27 | 1994-04-28 | Degussa | Anellierte Triazolverbindungen |
| IL107719A0 (en) * | 1992-12-21 | 1994-02-27 | Du Pont | Imidazolones their manufacture and their use as herbicides |
| DE4327027A1 (de) * | 1993-02-15 | 1994-08-18 | Bayer Ag | Imidazoazine |
| WO1994022860A1 (en) * | 1993-03-26 | 1994-10-13 | E.I. Du Pont De Nemours And Company | Herbicidal triazolinones |
| DE4309966A1 (de) * | 1993-03-26 | 1994-09-29 | Bayer Ag | Substituierte 1-Aryltriazolinone |
| JPH06345743A (ja) * | 1993-04-12 | 1994-12-20 | Sankyo Co Ltd | 除草性トリアゾール化合物 |
| BR9406971A (pt) * | 1993-06-23 | 1996-03-26 | Ciba Geigy Ag | Tiadiazabiciclodecanos herbicidas |
| AU678896B2 (en) * | 1994-02-16 | 1997-06-12 | Degussa A.G. | Herbicidal tricyclic heterocycles and bicyclic ureas |
| WO1995023509A1 (en) * | 1994-03-01 | 1995-09-08 | E.I. Du Pont De Nemours And Company | Herbicidal bicyclic hydantoins |
| DE4414568A1 (de) * | 1994-04-27 | 1995-11-02 | Bayer Ag | Heterocyclylbenzonitrile |
| EP0801068A4 (en) * | 1994-12-27 | 2000-08-23 | Sagami Chem Res | HYDANTOIN DERIVATIVES, PROCESS FOR PRODUCING THE SAME, AND HERBICIDES INCLUDING THEM AS ACTIVE INGREDIENTS |
-
1996
- 1996-10-08 BR BR9611133A patent/BR9611133A/pt not_active IP Right Cessation
- 1996-10-08 DK DK96937667T patent/DK0862571T3/da active
- 1996-10-08 EP EP96937667A patent/EP0862571B1/en not_active Expired - Lifetime
- 1996-10-08 CN CN96197871A patent/CN1202172A/zh active Pending
- 1996-10-08 IL IL12415896A patent/IL124158A/en not_active IP Right Cessation
- 1996-10-08 CA CA002235146A patent/CA2235146C/en not_active Expired - Fee Related
- 1996-10-08 TR TR1998/00718T patent/TR199800718T2/xx unknown
- 1996-10-08 HU HU9802363A patent/HUP9802363A3/hu unknown
- 1996-10-08 WO PCT/US1996/016111 patent/WO1997015576A1/en not_active Ceased
- 1996-10-08 AT AT96937667T patent/ATE231151T1/de not_active IP Right Cessation
- 1996-10-08 SK SK519-98A patent/SK51998A3/sk unknown
- 1996-10-08 DE DE69625825T patent/DE69625825T2/de not_active Expired - Fee Related
- 1996-10-08 PL PL96328095A patent/PL328095A1/xx unknown
- 1996-10-08 AU AU75153/96A patent/AU712362B2/en not_active Ceased
- 1996-10-08 ES ES96937667T patent/ES2191117T3/es not_active Expired - Lifetime
- 1996-10-08 KR KR1019980702984A patent/KR19990067047A/ko not_active Withdrawn
- 1996-10-08 JP JP9516120A patent/JPH11514370A/ja not_active Ceased
- 1996-10-08 CZ CZ981212A patent/CZ121298A3/cs unknown
- 1996-10-23 AR ARP960104871A patent/AR004082A1/es active IP Right Grant
- 1996-10-24 US US08/736,636 patent/US6060432A/en not_active Expired - Fee Related
- 1996-12-24 TW TW085116011A patent/TW357053B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| EP0862571B1 (en) | 2003-01-15 |
| HUP9802363A1 (hu) | 1999-01-28 |
| PL328095A1 (en) | 1999-01-04 |
| ES2191117T3 (es) | 2003-09-01 |
| JPH11514370A (ja) | 1999-12-07 |
| IL124158A (en) | 2004-06-20 |
| WO1997015576A1 (en) | 1997-05-01 |
| CA2235146A1 (en) | 1997-05-01 |
| DE69625825T2 (de) | 2003-09-04 |
| CN1202172A (zh) | 1998-12-16 |
| CA2235146C (en) | 2004-12-14 |
| DK0862571T3 (da) | 2003-04-28 |
| AR004082A1 (es) | 1998-09-30 |
| TR199800718T2 (xx) | 1998-08-21 |
| CZ121298A3 (cs) | 1998-07-15 |
| TW357053B (en) | 1999-05-01 |
| BR9611133A (pt) | 1999-05-25 |
| KR19990067047A (ko) | 1999-08-16 |
| ATE231151T1 (de) | 2003-02-15 |
| DE69625825D1 (de) | 2003-02-20 |
| AU7515396A (en) | 1997-05-15 |
| AU712362B2 (en) | 1999-11-04 |
| EP0862571A1 (en) | 1998-09-09 |
| HUP9802363A3 (en) | 1999-04-28 |
| US6060432A (en) | 2000-05-09 |
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