TW505640B - 3-heterocyclyl-substituted benzoyl derivatives - Google Patents

3-heterocyclyl-substituted benzoyl derivatives Download PDF

Info

Publication number: TW505640B
Authority: TW; Taiwan
Prior art keywords: alkyl; hydrogen; group; compound; ibl
Prior art date: 1997-01-17

Application number

TW087100502A

Other languages

English (en)

Chinese (zh)

Inventor

Joachim Rheinheimer

Ulf Misslitz

Helmut Walter

En Karl-Otto Westphal

Ernst Baumann

Original Assignee

Basf Ag

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

1997-01-17

Filing date

1998-01-15

Publication date

2002-10-11

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=7817606&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=TW505640(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1998-01-15 Application filed by Basf Ag filed Critical Basf Ag

2002-10-11 Application granted granted Critical

2002-10-11 Publication of TW505640B publication Critical patent/TW505640B/zh

Links

125000003236 benzoyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 title abstract description 4
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 287
239000001257 hydrogen Substances 0.000 claims abstract description 285
125000000217 alkyl group Chemical group 0.000 claims abstract description 92
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 85
150000002431 hydrogen Chemical group 0.000 claims abstract description 66
239000000203 mixture Chemical class 0.000 claims abstract description 56
125000003545 alkoxy group Chemical group 0.000 claims abstract description 34
229910052760 oxygen Inorganic materials 0.000 claims abstract description 33
229910052736 halogen Inorganic materials 0.000 claims abstract description 31
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 28
150000002367 halogens Chemical class 0.000 claims abstract description 24
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 24
238000000034 method Methods 0.000 claims abstract description 22
150000003839 salts Chemical class 0.000 claims abstract description 20
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 11
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 10
229910052717 sulfur Inorganic materials 0.000 claims abstract description 10
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 9
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 4
125000003226 pyrazolyl group Chemical group 0.000 claims abstract 2
-1 phenylfluorenyl Chemical class 0.000 claims description 579
150000001875 compounds Chemical class 0.000 claims description 430
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 198
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 39
150000003937 benzamidines Chemical class 0.000 claims description 37
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 31
239000001301 oxygen Substances 0.000 claims description 31
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
239000002253 acid Substances 0.000 claims description 27
241000196324 Embryophyta Species 0.000 claims description 26
NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 20
239000007789 gas Substances 0.000 claims description 16
230000002363 herbicidal effect Effects 0.000 claims description 16
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 13
239000000052 vinegar Substances 0.000 claims description 13
235000021419 vinegar Nutrition 0.000 claims description 13
101100134925 Gallus gallus COR6 gene Proteins 0.000 claims description 12
125000001424 substituent group Chemical group 0.000 claims description 12
150000001558 benzoic acid derivatives Chemical class 0.000 claims description 10
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
125000000623 heterocyclic group Chemical group 0.000 claims description 8
239000005711 Benzoic acid Substances 0.000 claims description 7
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 7
235000010233 benzoic acid Nutrition 0.000 claims description 7
239000011593 sulfur Substances 0.000 claims description 7
239000003054 catalyst Substances 0.000 claims description 6
238000006467 substitution reaction Methods 0.000 claims description 6
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
239000002671 adjuvant Substances 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
230000007062 hydrolysis Effects 0.000 claims description 4
238000006460 hydrolysis reaction Methods 0.000 claims description 4
150000004702 methyl esters Chemical class 0.000 claims description 4
230000000269 nucleophilic effect Effects 0.000 claims description 4
XHTUOWXUBNMVEU-UHFFFAOYSA-N 1-benzoyl-5-ethyl-5-(3-methylbutyl)-1,3-diazinane-2,4,6-trione Chemical group O=C1C(CC)(CCC(C)C)C(=O)NC(=O)N1C(=O)C1=CC=CC=C1 XHTUOWXUBNMVEU-UHFFFAOYSA-N 0.000 claims description 3
PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical group NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 claims description 3
238000009472 formulation Methods 0.000 claims description 3
238000006462 rearrangement reaction Methods 0.000 claims description 3
WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
150000001735 carboxylic acids Chemical class 0.000 claims 2
RMMKGDVKSFHHAX-UHFFFAOYSA-N 1,3-oxazole;pyridine Chemical compound C1=COC=N1.C1=CC=NC=C1 RMMKGDVKSFHHAX-UHFFFAOYSA-N 0.000 claims 1
QVCIPIYWPSPRFA-UHFFFAOYSA-N 1-hydroxypyrazole Chemical compound ON1C=CC=N1 QVCIPIYWPSPRFA-UHFFFAOYSA-N 0.000 claims 1
QZVRXWBKQJFSLP-UHFFFAOYSA-N 2-ethyl-1h-pyrazol-3-one Chemical compound CCN1NC=CC1=O QZVRXWBKQJFSLP-UHFFFAOYSA-N 0.000 claims 1
XKHGDOMATZKMIL-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole-5-carbonitrile Chemical compound N#CC1CC=NO1 XKHGDOMATZKMIL-UHFFFAOYSA-N 0.000 claims 1
TYWCCQQJFXUKRN-UHFFFAOYSA-N 4-methyl-1,2-dihydropyrazol-3-one Chemical compound CC1=CNNC1=O TYWCCQQJFXUKRN-UHFFFAOYSA-N 0.000 claims 1
241000282620 Hylobates sp. Species 0.000 claims 1
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
229910021386 carbon form Inorganic materials 0.000 claims 1
230000007774 longterm Effects 0.000 claims 1
125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 11
125000004438 haloalkoxy group Chemical group 0.000 abstract description 5
125000004995 haloalkylthio group Chemical group 0.000 abstract description 4
239000000543 intermediate Substances 0.000 abstract description 4
230000008569 process Effects 0.000 abstract description 3
125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 abstract 1
125000004663 dialkyl amino group Chemical group 0.000 abstract 1
125000004440 haloalkylsulfinyl group Chemical group 0.000 abstract 1
230000000875 corresponding effect Effects 0.000 description 258
238000011049 filling Methods 0.000 description 159
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 129
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 120
239000000460 chlorine Substances 0.000 description 101
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 93
230000002079 cooperative effect Effects 0.000 description 79
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 51
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 42
229910052757 nitrogen Inorganic materials 0.000 description 38
125000006125 ethylsulfonyl group Chemical group 0.000 description 36
QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 32
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 32
229910052801 chlorine Inorganic materials 0.000 description 31
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 31
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 28
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
239000002585 base Substances 0.000 description 27
239000000243 solution Substances 0.000 description 27
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 26
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 25
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 22
239000002904 solvent Substances 0.000 description 22
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 21
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 20
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 19
239000004480 active ingredient Substances 0.000 description 19
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 19
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
229910052794 bromium Inorganic materials 0.000 description 17
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 15
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 14
125000001309 chloro group Chemical group Cl* 0.000 description 14
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 14
125000006126 n-butyl sulfonyl group Chemical group 0.000 description 14
125000006124 n-propyl sulfonyl group Chemical group 0.000 description 14
238000012360 testing method Methods 0.000 description 14
238000002844 melting Methods 0.000 description 13
230000008018 melting Effects 0.000 description 13
150000001412 amines Chemical class 0.000 description 12
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 11
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 11
239000012074 organic phase Substances 0.000 description 11
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
241001674048 Phthiraptera Species 0.000 description 10
QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 10
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 9
239000011737 fluorine Substances 0.000 description 9
229910052731 fluorine Inorganic materials 0.000 description 9
125000005843 halogen group Chemical group 0.000 description 9
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 9
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
239000008346 aqueous phase Substances 0.000 description 8
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
238000011282 treatment Methods 0.000 description 8
238000005481 NMR spectroscopy Methods 0.000 description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 7
239000006185 dispersion Substances 0.000 description 7
238000004821 distillation Methods 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
150000002825 nitriles Chemical class 0.000 description 7
239000003921 oil Substances 0.000 description 7
235000019198 oils Nutrition 0.000 description 7
239000000843 powder Substances 0.000 description 7
239000000047 product Substances 0.000 description 7
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 7
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
239000007787 solid Substances 0.000 description 7
239000007858 starting material Substances 0.000 description 7
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 6
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 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
229960004365 benzoic acid Drugs 0.000 description 6
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 6
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
238000007639 printing Methods 0.000 description 6
150000003254 radicals Chemical class 0.000 description 6
238000010992 reflux Methods 0.000 description 6
239000011734 sodium Substances 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
238000003756 stirring Methods 0.000 description 6
239000000126 substance Substances 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 5
125000006519 CCH3 Chemical group 0.000 description 5
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 5
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
150000001450 anions Chemical class 0.000 description 5
239000012141 concentrate Substances 0.000 description 5
244000038559 crop plants Species 0.000 description 5
239000000839 emulsion Substances 0.000 description 5
239000004009 herbicide Substances 0.000 description 5
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
229910052740 iodine Inorganic materials 0.000 description 5
239000007788 liquid Substances 0.000 description 5
229940095102 methyl benzoate Drugs 0.000 description 5
239000001632 sodium acetate Substances 0.000 description 5
235000017281 sodium acetate Nutrition 0.000 description 5
239000004575 stone Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 description 4
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
VEDTXTNSFWUXGQ-UHFFFAOYSA-N Carbophenothion Chemical group CCOP(=S)(OCC)SCSC1=CC=C(Cl)C=C1 VEDTXTNSFWUXGQ-UHFFFAOYSA-N 0.000 description 4
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
241000209140 Triticum Species 0.000 description 4
235000021307 Triticum Nutrition 0.000 description 4
240000008042 Zea mays Species 0.000 description 4
150000001299 aldehydes Chemical class 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
229940050390 benzoate Drugs 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
239000000969 carrier Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
125000004966 cyanoalkyl group Chemical group 0.000 description 4
125000004705 ethylthio group Chemical group C(C)S* 0.000 description 4
125000001153 fluoro group Chemical group F* 0.000 description 4
230000035784 germination Effects 0.000 description 4
230000012010 growth Effects 0.000 description 4
150000007857 hydrazones Chemical class 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 4
239000012071 phase Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000008159 sesame oil Substances 0.000 description 4
235000011803 sesame oil Nutrition 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
125000003396 thiol group Chemical group [H]S* 0.000 description 4
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 4
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 3
RRFGGUXLGOVPOP-UHFFFAOYSA-N 2-chloro-3-methyl-4-methylsulfonylbenzoic acid Chemical compound CC1=C(Cl)C(C(O)=O)=CC=C1S(C)(=O)=O RRFGGUXLGOVPOP-UHFFFAOYSA-N 0.000 description 3
241000723377 Coffea Species 0.000 description 3
235000010469 Glycine max Nutrition 0.000 description 3
244000068988 Glycine max Species 0.000 description 3
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
240000007594 Oryza sativa Species 0.000 description 3
235000007164 Oryza sativa Nutrition 0.000 description 3
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150000003217 pyrazoles Chemical class 0.000 description 1
LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 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
206010037844 rash Diseases 0.000 description 1
235000013526 red clover Nutrition 0.000 description 1
230000009467 reduction Effects 0.000 description 1
BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
235000020637 scallop Nutrition 0.000 description 1
125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000013049 sediment Substances 0.000 description 1
150000007659 semicarbazones Chemical class 0.000 description 1
239000010703 silicon Substances 0.000 description 1
239000000779 smoke Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
PYODKQIVQIVELM-UHFFFAOYSA-M sodium;2,3-bis(2-methylpropyl)naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 PYODKQIVQIVELM-UHFFFAOYSA-M 0.000 description 1
238000009331 sowing Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
229940071182 stannate Drugs 0.000 description 1
125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical group CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
KBPHJBAIARWVSC-XQIHNALSSA-N trans-lutein Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C(=CC(O)CC2(C)C)C KBPHJBAIARWVSC-XQIHNALSSA-N 0.000 description 1
229910001428 transition metal ion Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
229940087291 tridecyl alcohol Drugs 0.000 description 1
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
229910052722 tritium Inorganic materials 0.000 description 1
230000002485 urinary effect Effects 0.000 description 1
210000002700 urine Anatomy 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
238000005945 von Braun degradation reaction Methods 0.000 description 1
235000020234 walnut Nutrition 0.000 description 1
239000004562 water dispersible granule Substances 0.000 description 1
239000012991 xanthate Substances 0.000 description 1
FJHBOVDFOQMZRV-XQIHNALSSA-N xanthophyll Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C=C(C)C(O)CC2(C)C FJHBOVDFOQMZRV-XQIHNALSSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D411/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D411/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/20—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings condensed with carbocyclic rings or ring systems
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings

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)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Thiazole And Isothizaole Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pyridine Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

TW087100502A 1997-01-17 1998-01-15 3-heterocyclyl-substituted benzoyl derivatives TW505640B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19701446		1997-01-17

Publications (1)

Publication Number	Publication Date
TW505640B true TW505640B (en)	2002-10-11

Family

ID=7817606

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW087100502A TW505640B (en)	1997-01-17	1998-01-15	3-heterocyclyl-substituted benzoyl derivatives

Country Status (33)

Country	Link
US (3)	US9045465B1 (2)
EP (1)	EP0958291B1 (2)
JP (1)	JP4306805B2 (2)
KR (2)	KR20050111648A (2)
CN (1)	CN1117750C (2)
AR (1)	AR011539A1 (2)
AT (1)	ATE421514T1 (2)
AU (3)	AU6092998A (2)
BG (1)	BG64232B1 (2)
BR (1)	BR9806778B1 (2)
CA (1)	CA2278331C (2)
CZ (1)	CZ297554B6 (2)
DE (1)	DE59814338D1 (2)
DK (1)	DK0958291T3 (2)
EA (1)	EA006633B1 (2)
EE (1)	EE05455B1 (2)
ES (1)	ES2318868T3 (2)
GE (1)	GEP20022617B (2)
HU (1)	HU228459B1 (2)
IL (1)	IL130777A (2)
IN (2)	IN1998CH00104A (2)
MX (1)	MX220140B (2)
NO (1)	NO313914B1 (2)
NZ (1)	NZ336992A (2)
PL (1)	PL195240B1 (2)
PT (1)	PT958291E (2)
SI (1)	SI0958291T1 (2)
SK (1)	SK286069B6 (2)
TR (1)	TR199901667T2 (2)
TW (1)	TW505640B (2)
UA (1)	UA54489C2 (2)
WO (1)	WO1998031681A1 (2)
ZA (2)	ZA98363B (2)

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DK1852424T3 (da)	1998-05-11	2012-07-23	Basf Se	Fremgangsmåde til fremstilling af isoxazolin-3-YL-acylbenzener
DE19852095A1 (de)	1998-11-12	2000-05-18	Basf Ag	Verfahren zur Herstellung von 2-Alkyl-3-(4,5-dihydroisoxazol-3-yl)-acylbenzolen
CN101176450A (zh)	1998-06-16	2008-05-14	巴斯福股份公司	具有增效效果的除草混合物
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AU3329800A (en) *	1999-03-29	2000-10-16	Nippon Soda Co., Ltd.	Process for the preparation of (e)-3-(1-propenyl)isoxazoline
EP1174409A4 (en) *	1999-04-28	2003-05-02	Nippon Soda Co	NOVEL BICYCLOHEPTENE DERIVATIVES AND THEIR PREPARATION PROCESS
AR024845A1 (es)	1999-08-06	2002-10-30	Basf Ag	Derivados de 1-cicloalquilpirazolil-benzoilo y sus sales, procedimiento para obtener dichos derivados, las composiciones herbicidas que los contienen y supreparacion, el procedimiento para controlar el crecimiento de plantas indeseadas con dichos derivados y el uso de dichos derivados como herbicida
DE19946853A1 (de)	1999-09-30	2001-04-05	Bayer Ag	Substituierte Arylketone
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AU781318B2 (en) *	1999-12-22	2005-05-19	Basf Aktiengesellschaft	3-(4,5-dihydroisoxazole-5-yl)benzoylpyrazole
AU784813B2 (en)	2000-01-17	2006-06-29	Bayer Aktiengesellschaft	Substituted aryl ketones
US6388135B1 (en)	2000-06-30	2002-05-14	Basf Aktiengesellschaft	Preparation of 4-bromoaniline derivatives
JP4990472B2 (ja)	2000-07-17	2012-08-01	ビーエーエスエフソシエタス・ヨーロピア	４−チオアルキルブロモベンゼン誘導体の製造方法
BR0209099B1 (pt)	2001-04-27	2013-04-24		composiÇço seletivamente herbicida e mÉtodo para controlar o desenvolvimento de plantas indesejadas em colheitas de plantas éteis.
DE10136449A1 (de) *	2001-05-09	2002-11-14	Bayer Ag	Substituierte Arylketone
WO2002090336A1 (de)	2001-05-09	2002-11-14	Bayer Cropscience Ag	Substituierte arylketone
DE10138577A1 (de) *	2001-05-21	2002-11-28	Bayer Ag	Substituierte Benzoylpyrazole
DE10142333A1 (de) *	2001-08-30	2003-03-20	Bayer Cropscience Ag	Herbizide Mischungen auf Basis von substituierten Arylketonen
DE10142336A1 (de)	2001-08-30	2003-03-20	Bayer Cropscience Ag	Selektive Herbizide enthaltend ein Tetrazolinon-Derivat
DE10142334A1 (de) *	2001-08-30	2003-03-20	Bayer Cropscience Ag	Herbizide auf Basis von substituierten Arylketonen
DE10146591A1 (de)	2001-09-21	2003-04-10	Bayer Cropscience Ag	Herbizide auf Basis von substituierten Thien-3-yl-sulfonylamino(thio)carbonyl-triazolin(thi)onen
DE10206792A1 (de)	2002-02-19	2003-08-28	Bayer Cropscience Ag	Substituierte Arylketone
DE10209645A1 (de) *	2002-03-05	2003-09-18	Bayer Cropscience Ag	Substituierte Arylketone
WO2003084331A1 (de) *	2002-04-10	2003-10-16	Basf Aktiengesellschaft	Verfahren zur erhöhung der widerstandskraft von pflanzen gegen die phytotoxizität von agrochemikalien
JP2005533058A (ja)	2002-06-17	2005-11-04	メルク　エンド　カムパニー　インコーポレーテッド	Ｅｄｇ受容体アゴニストとしての１−（（５−アリール−１，２，４−オキサジアゾール−３−イル）ベンジル）アゼチジン−３−カルボキシラートおよび１−（（５−アリール−１，２，４−オキサジアゾール−３−イル）ベンジル）ピロリジン−３−カルボキシラート
EA011503B1 (ru) *	2002-07-22	2009-04-28	Басф Акциенгезельшафт	Гербицидные смеси с синергическим действием
EP1917857A1 (en)	2002-07-24	2008-05-07	Basf Se	Synergistically acting herbicidal mixtures
MXPA05008783A (es) *	2003-03-13	2005-10-18	Basf Ag	Mezclas herbicidas que comprenden un protector.
DE102004010813A1 (de)	2004-03-05	2005-11-10	Bayer Cropscience Ag	Neue Herbizide auf Basis von substituierten Thien-3-yl-sulfonylamino(thio)carbonyltriazolin(thi)onen und 4-HPPD-Hemmstoffen
US20070060478A1 (en) *	2005-09-13	2007-03-15	Basf Aktiengesellschaft	Herbicidal mixtures comprising a safener
US20070123426A1 (en) *	2005-11-25	2007-05-31	Basf Aktiengesellschaft	Mixtures
AR056889A1 (es)	2005-12-15	2007-10-31	Ishihara Sangyo Kaisha	Compuestos benzoilpirazol y herbicidas que los contienen
UA91446C2 (ru)	2006-08-04	2010-07-26	Басф Се	Неводный и водный концентраты действующего вещества с гербицидным действием, способ борьбы с нежелательным ростом растений
UA89599C2 (uk) *	2006-08-04	2010-02-10	Басф Се	Водний концентрат діючої речовини з гербіцидною дією та спосіб боротьби з небажаним ростом рослин
PL2096922T3 (pl)	2006-11-27	2012-09-28	Basf Se	Sposób zwalczania chwastów trawiastych za pomocą chwastobójczo skutecznej kompozycji zawierającej jednowartościową sól 4-[2-metylo-3-(4,5-dihydroizoksazol-3-ilo)-4-metylosulfonylo-benzoilo]-1-metylo-5-hydroksy-1H-pirazolu
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SI2173742T1 (sl)	2007-07-06	2012-03-30	Basf Se	Kristalna oblika dihidro izoksazolilmetil metilsulfonil fenil hidroksi metil h pirazol il metanona
EP2052615A1 (de)	2007-10-24	2009-04-29	Bayer CropScience AG	Herbizid-Kombination
DE102008037628A1 (de)	2008-08-14	2010-02-18	Bayer Crop Science Ag	Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden
WO2011067184A1 (de)	2009-12-01	2011-06-09	Basf Se	3- (4, 5 -dihydroisoxazol- 5 -yl) benzoylpyrazolverbindungen und ihre mischungen mit safenern
BR112014011534A2 (pt)	2011-11-14	2017-05-09	Basf Se	composto, composição, uso de um composto e método para controle de vegetação indesejada
JP6032272B2 (ja)	2012-03-16	2016-11-24	日本ゼオン株式会社	開環メタセシス重合体水素化物の製造方法及び樹脂組成物
JP2015519314A (ja)	2012-04-27	2015-07-09	ビーエーエスエフソシエタス・ヨーロピアＢａｓｆＳｅ	置換型ｎ−（テトラゾール−５−イル）−およびｎ−（トリアゾール−５−イル）ピリジン−３−イル−カルボキサミド化合物ならびに除草剤としてのそれらの使用
JP6141408B2 (ja)	2012-04-27	2017-06-07	ビーエーエスエフソシエタス・ヨーロピアＢａｓｆＳｅ	置換型ｎ−（テトラゾール−５−イル）−およびｎ−（トリアゾール−５−イル）アリールカルボキサミド化合物ならびに除草剤としてのそれらの使用
BR112015028597A2 (pt)	2013-05-15	2017-07-25	Basf Se	n-(tetrazol-5-il)- e n-(5-triazol-il)arilcarboxamidas, composição, utilização de um composto e método para o controle da vegetação
WO2014184058A1 (en)	2013-05-15	2014-11-20	Basf Se	Substituted 1,2,5-oxadiazole compounds and their use as herbicides
WO2015007564A1 (en)	2013-07-18	2015-01-22	Basf Se	Substituted n-(1,2,4-triazol-3-yl)arylcarboxamide compounds and their use as herbicides
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1998
- 1998-01-08 DE DE59814338T patent/DE59814338D1/de not_active Expired - Lifetime
- 1998-01-08 DK DK98905274T patent/DK0958291T3/da active
- 1998-01-08 SI SI9830916T patent/SI0958291T1/sl unknown
- 1998-01-08 EE EEP199900290A patent/EE05455B1/xx unknown
- 1998-01-08 EP EP98905274A patent/EP0958291B1/de not_active Expired - Lifetime
- 1998-01-08 WO PCT/EP1998/000069 patent/WO1998031681A1/de not_active Ceased
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- 1998-01-08 BR BRPI9806778-8A patent/BR9806778B1/pt not_active IP Right Cessation
- 1998-01-08 US US09/091,300 patent/US9045465B1/en not_active Expired - Fee Related
- 1998-01-08 CN CN98802797A patent/CN1117750C/zh not_active Expired - Lifetime
- 1998-01-08 AT AT98905274T patent/ATE421514T1/de active
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- 1998-01-08 ES ES98905274T patent/ES2318868T3/es not_active Expired - Lifetime
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2000
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Also Published As

Publication number	Publication date
KR20050111648A (ko)	2005-11-25
CZ297554B6 (cs)	2007-02-07
EP0958291A1 (de)	1999-11-24
WO1998031681A1 (de)	1998-07-23
KR20000070236A (ko)	2000-11-25
SK90399A3 (en)	1999-12-10
US7232792B2 (en)	2007-06-19
DK0958291T3 (da)	2009-05-04
EA199900614A1 (ru)	2000-02-28
IN1998CH00104A (2)	2005-03-04
AU2004203481B2 (en)	2007-10-18
AU9139501A (en)	2002-01-10
JP2001508458A (ja)	2001-06-26
HUP0001493A3 (en)	2001-02-28
IL130777A (en)	2005-06-19
HUP0001493A2 (hu)	2000-08-28
TR199901667T2 (xx)	1999-10-21
US20080039327A1 (en)	2008-02-14
BR9806778B1 (pt)	2009-12-01
EA006633B1 (ru)	2006-02-24
MX220140B (es)	2004-04-28
PL334847A1 (en)	2000-03-27
BG103658A (en)	2000-06-30
CN1248255A (zh)	2000-03-22
IL130777A0 (en)	2001-01-28
PL195240B1 (pl)	2007-08-31
SI0958291T1 (sl)	2009-04-30
AU2004203481A1 (en)	2004-08-26
EP0958291B1 (de)	2009-01-21
NZ336992A (en)	2001-08-31
CN1117750C (zh)	2003-08-13
JP4306805B2 (ja)	2009-08-05
BR9806778A (pt)	2000-05-16
ZA98362B (en)	1999-07-16
GEP20022617B (en)	2002-01-25
MX9906602A (es)	1999-10-31
EE9900290A (et)	2000-02-15
ES2318868T3 (es)	2009-05-01
ZA98363B (en)	1999-07-16
CZ252399A3 (cs)	2000-04-12
CA2278331C (en)	2008-11-18
CA2278331A1 (en)	1998-07-23
KR100550482B1 (ko)	2006-02-09
HU228459B1 (en)	2013-03-28
US7608564B2 (en)	2009-10-27
US9045465B1 (en)	2015-06-02
AR011539A1 (es)	2000-08-30
EE05455B1 (et)	2011-08-15
IN1998CH00103A (en)	2005-03-04
US20020025910A1 (en)	2002-02-28
AU6092998A (en)	1998-08-07
BG64232B1 (bg)	2004-06-30
UA54489C2 (uk)	2003-03-17
NO993521L (no)	1999-09-15
SK286069B6 (sk)	2008-02-05
ATE421514T1 (de)	2009-02-15
NO313914B1 (no)	2002-12-23
PT958291E (pt)	2009-02-11
NO993521D0 (no)	1999-07-16
DE59814338D1 (de)	2009-03-12

Legal Events

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2003-03-10	GD4A	Issue of patent certificate for granted invention patent
2018-02-21	MK4A	Expiration of patent term of an invention patent

Publication	Publication Date	Title
TW505640B (en)	2002-10-11	3-heterocyclyl-substituted benzoyl derivatives
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BR9915950B1 (pt)	2012-01-10	benzoilpirazol substituìdo por 3-heterociclila, processo para preparar benzoilpirazóis substituìdos por 3-heterociclila, composição, processo para preparar uma composição, processo para controlar vegetação indesejável, e, uso dos benzoilpirazóis substituìdos por 3-heterociclila.
EP1240163A1 (de)	2002-09-18	3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazole
EP1200429B1 (de)	2004-06-16	1-cycloalkylpyrazolyl-benzoyl-derivate
EP1135387B1 (de)	2002-11-06	3-(heterocyclyl)-benzoylpyrazol-derivate
DE19936520A1 (de)	2001-02-15	3-(Heterocyclyl)-benzoylpyrazolyl-Derivate
MXPA97005015A (es)		2-fenilpiridinas sustituidas, su procedimiento deobtencion y las composiciones herbicidas que las contie
MXPA01005566A (en)	2001-12-04	3-(heterocyclyl)-benzoylpyrazole-derivatives
MXPA01005666A (en)	2002-05-09	Sizing composition
MXPA97004925A (en)		2-fenil pyridine sustitui
MXPA97004926A (en)	1998-07-03	2-substitute phenilpiridines, procedure parasu obtaining and the herbicidal compositions that contain them