BRPI0715451A2 - furil-sulfonilamino(tio)carbonil-triazolin(ti)onas substituÍdas - Google Patents

furil-sulfonilamino(tio)carbonil-triazolin(ti)onas substituÍdas Download PDF

Info

Publication number: BRPI0715451A2
Authority: BR; Brazil
Prior art keywords: oc3h7; optionally substituted; cyano; alkyl; chlorine
Prior art date: 2006-07-12

Application number

BRPI0715451-8A

Other languages

English (en)

Portuguese (pt)

Inventor

Christian Waldraff

Martin Hills

Heinz Kehne

Chris Rosinger

Ernst Gesing

Klaus-Helmut Mueller

Dieter Feucht

Original Assignee

Bayer Cropscience 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.)

2006-07-12

Filing date

2007-07-05

Publication date

2013-02-26

2007-07-05 Application filed by Bayer Cropscience Ag filed Critical Bayer Cropscience Ag

2013-02-26 Publication of BRPI0715451A2 publication Critical patent/BRPI0715451A2/pt

Links

-1 furyl sulfonylamino (thio) carbonyl triazolin Chemical compound 0.000 title claims abstract description 248
150000001875 compounds Chemical class 0.000 claims abstract description 139
238000000034 method Methods 0.000 claims abstract description 52
230000008569 process Effects 0.000 claims abstract description 45
238000002360 preparation method Methods 0.000 claims abstract description 30
150000003839 salts Chemical class 0.000 claims abstract description 23
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 335
239000001257 hydrogen Substances 0.000 claims description 112
229910052739 hydrogen Inorganic materials 0.000 claims description 112
239000000460 chlorine Chemical group 0.000 claims description 110
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 105
229910052801 chlorine Inorganic materials 0.000 claims description 105
229910052736 halogen Inorganic materials 0.000 claims description 100
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 94
125000004432 carbon atom Chemical group C* 0.000 claims description 94
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 90
241000196324 Embryophyta Species 0.000 claims description 87
150000002367 halogens Chemical class 0.000 claims description 82
125000004093 cyano group Chemical group *C#N 0.000 claims description 76
125000000217 alkyl group Chemical group 0.000 claims description 74
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 70
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 64
239000011737 fluorine Substances 0.000 claims description 63
229910052731 fluorine Inorganic materials 0.000 claims description 63
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 63
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 63
125000001153 fluoro group Chemical group F* 0.000 claims description 62
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 54
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 48
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 47
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 47
229910052794 bromium Inorganic materials 0.000 claims description 47
CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical group FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 39
125000000623 heterocyclic group Chemical group 0.000 claims description 36
125000003342 alkenyl group Chemical group 0.000 claims description 35
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 35
125000000304 alkynyl group Chemical group 0.000 claims description 34
239000000203 mixture Substances 0.000 claims description 32
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 32
125000003118 aryl group Chemical group 0.000 claims description 30
125000000753 cycloalkyl group Chemical group 0.000 claims description 29
229910052760 oxygen Inorganic materials 0.000 claims description 29
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 25
125000003545 alkoxy group Chemical group 0.000 claims description 24
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 24
239000001301 oxygen Substances 0.000 claims description 24
125000004414 alkyl thio group Chemical group 0.000 claims description 22
125000003710 aryl alkyl group Chemical group 0.000 claims description 21
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 21
230000002363 herbicidal effect Effects 0.000 claims description 21
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 20
238000006243 chemical reaction Methods 0.000 claims description 19
125000003302 alkenyloxy group Chemical group 0.000 claims description 18
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 18
239000003085 diluting agent Substances 0.000 claims description 18
125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 18
229910052717 sulfur Chemical group 0.000 claims description 18
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 17
125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 16
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 15
239000011593 sulfur Chemical group 0.000 claims description 15
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 15
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 13
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 13
125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 12
125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 12
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 11
239000011734 sodium Substances 0.000 claims description 11
229910052708 sodium Inorganic materials 0.000 claims description 11
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 claims description 10
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 10
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
125000005133 alkynyloxy group Chemical group 0.000 claims description 10
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 9
125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
125000003282 alkyl amino group Chemical group 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 8
125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 8
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 8
125000004663 dialkyl amino group Chemical group 0.000 claims description 8
IEKOSPNJXYCZHY-UHFFFAOYSA-N furan-2-sulfonyl chloride Chemical class ClS(=O)(=O)C1=CC=CO1 IEKOSPNJXYCZHY-UHFFFAOYSA-N 0.000 claims description 8
125000002541 furyl group Chemical group 0.000 claims description 8
125000001544 thienyl group Chemical group 0.000 claims description 8
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 7
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 7
125000004104 aryloxy group Chemical group 0.000 claims description 7
125000006310 cycloalkyl amino group Chemical group 0.000 claims description 7
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 7
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 6
125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 6
RHBMVXBGYGIDJN-UHFFFAOYSA-N furan-2-sulfonamide Chemical class NS(=O)(=O)C1=CC=CO1 RHBMVXBGYGIDJN-UHFFFAOYSA-N 0.000 claims description 6
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 6
125000003566 oxetanyl group Chemical group 0.000 claims description 6
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 6
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
125000005958 tetrahydrothienyl group Chemical group 0.000 claims description 6
125000002053 thietanyl group Chemical group 0.000 claims description 6
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
125000006319 alkynyl amino group Chemical group 0.000 claims description 5
239000012752 auxiliary agent Substances 0.000 claims description 5
125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 5
229910052740 iodine Inorganic materials 0.000 claims description 5
230000008635 plant growth Effects 0.000 claims description 5
125000004434 sulfur atom Chemical group 0.000 claims description 5
239000004094 surface-active agent Substances 0.000 claims description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
125000005108 alkenylthio group Chemical group 0.000 claims description 4
150000003863 ammonium salts Chemical class 0.000 claims description 4
239000011575 calcium Substances 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 4
125000005366 cycloalkylthio group Chemical group 0.000 claims description 4
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
239000011630 iodine Substances 0.000 claims description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 3
125000006323 alkenyl amino group Chemical group 0.000 claims description 3
125000005109 alkynylthio group Chemical group 0.000 claims description 3
125000004659 aryl alkyl thio group Chemical group 0.000 claims description 3
125000001769 aryl amino group Chemical group 0.000 claims description 3
125000005110 aryl thio group Chemical group 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
229910052791 calcium Inorganic materials 0.000 claims description 3
150000003857 carboxamides Chemical class 0.000 claims description 3
125000006125 ethylsulfonyl group Chemical group 0.000 claims description 3
229910052751 metal Inorganic materials 0.000 claims description 3
239000002184 metal Substances 0.000 claims description 3
125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 3
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 3
125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
229910021529 ammonia Inorganic materials 0.000 claims description 2
125000001691 aryl alkyl amino group Chemical group 0.000 claims description 2
WGQKYBSKWIADBV-UHFFFAOYSA-O benzylaminium Chemical compound [NH3+]CC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-O 0.000 claims description 2
125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 claims description 2
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
239000011777 magnesium Substances 0.000 claims description 2
229910052749 magnesium Inorganic materials 0.000 claims description 2
239000011591 potassium Substances 0.000 claims description 2
229910052700 potassium Inorganic materials 0.000 claims description 2
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000006320 propynyl amino group Chemical group 0.000 claims description 2
238000006467 substitution reaction Methods 0.000 claims description 2
RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 2
NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims 1
MUQNGPZZQDCDFT-JNQJZLCISA-N Halcinonide Chemical group C1CC2=CC(=O)CC[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CCl)[C@@]1(C)C[C@@H]2O MUQNGPZZQDCDFT-JNQJZLCISA-N 0.000 claims 1
241000610375 Sparisoma viride Species 0.000 claims 1
229940028332 halog Drugs 0.000 claims 1
229910052738 indium Inorganic materials 0.000 claims 1
APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical group [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
125000006324 propenyl amino group Chemical group 0.000 claims 1
125000000547 substituted alkyl group Chemical group 0.000 claims 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims 1
150000003567 thiocyanates Chemical class 0.000 claims 1
239000004009 herbicide Substances 0.000 abstract description 24
238000002844 melting Methods 0.000 description 60
230000008018 melting Effects 0.000 description 60
150000003254 radicals Chemical class 0.000 description 52
239000013543 active substance Substances 0.000 description 50
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
239000007858 starting material Substances 0.000 description 22
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
150000002148 esters Chemical class 0.000 description 20
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238000009472 formulation Methods 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
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230000000694 effects Effects 0.000 description 13
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125000005843 halogen group Chemical group 0.000 description 12
239000000843 powder Substances 0.000 description 12
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GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 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
MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 1
OYJMHAFVOZPIOY-UHFFFAOYSA-N propan-2-yl 2-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]benzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1 OYJMHAFVOZPIOY-UHFFFAOYSA-N 0.000 description 1
FROBCXTULYFHEJ-OAHLLOKOSA-N propaquizafop Chemical compound C1=CC(O[C@H](C)C(=O)OCCON=C(C)C)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 FROBCXTULYFHEJ-OAHLLOKOSA-N 0.000 description 1
WJNRPILHGGKWCK-UHFFFAOYSA-N propazine Chemical compound CC(C)NC1=NC(Cl)=NC(NC(C)C)=N1 WJNRPILHGGKWCK-UHFFFAOYSA-N 0.000 description 1
VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
DVBARFVOVUTLAH-UHFFFAOYSA-N propyl 5,5-diphenyl-4h-1,2-oxazole-3-carboxylate Chemical compound C1C(C(=O)OCCC)=NOC1(C=1C=CC=CC=1)C1=CC=CC=C1 DVBARFVOVUTLAH-UHFFFAOYSA-N 0.000 description 1
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
NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
239000003223 protective agent Substances 0.000 description 1
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239000008262 pumice Substances 0.000 description 1
YXIIPOGUBVYZIW-UHFFFAOYSA-N pyraflufen Chemical compound ClC1=C(OC(F)F)N(C)N=C1C1=CC(OCC(O)=O)=C(Cl)C=C1F YXIIPOGUBVYZIW-UHFFFAOYSA-N 0.000 description 1
VTRWMTJQBQJKQH-UHFFFAOYSA-N pyributicarb Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C(C=CC=2)C(C)(C)C)=N1 VTRWMTJQBQJKQH-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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239000010453 quartz Substances 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
ALZOLUNSQWINIR-UHFFFAOYSA-N quinmerac Chemical compound OC(=O)C1=C(Cl)C=CC2=CC(C)=CN=C21 ALZOLUNSQWINIR-UHFFFAOYSA-N 0.000 description 1
ABOOPXYCKNFDNJ-SNVBAGLBSA-N quizalofop-P Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 ABOOPXYCKNFDNJ-SNVBAGLBSA-N 0.000 description 1
BACHBFVBHLGWSL-JTQLQIEISA-N rac-diclofop methyl Natural products C1=CC(O[C@@H](C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-JTQLQIEISA-N 0.000 description 1
229910052705 radium Inorganic materials 0.000 description 1
238000010992 reflux Methods 0.000 description 1
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229910052701 rubidium Inorganic materials 0.000 description 1
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229910052624 sepiolite Inorganic materials 0.000 description 1
235000019355 sepiolite Nutrition 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 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
RVULBHWZFCBODE-UHFFFAOYSA-M sodium;5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate Chemical compound [Na+].C1=C([N+]([O-])=O)C(C(=O)[O-])=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 RVULBHWZFCBODE-UHFFFAOYSA-M 0.000 description 1
MZSDGDXXBZSFTG-UHFFFAOYSA-M sodium;benzenesulfonate Chemical class [Na+].[O-]S(=O)(=O)C1=CC=CC=C1 MZSDGDXXBZSFTG-UHFFFAOYSA-M 0.000 description 1
JRQGDDUXDKCWRF-UHFFFAOYSA-M sodium;n-(2-methoxycarbonylphenyl)sulfonyl-4-methyl-5-oxo-3-propoxy-1,2,4-triazole-1-carboximidate Chemical compound [Na+].O=C1N(C)C(OCCC)=NN1C(=O)[N-]S(=O)(=O)C1=CC=CC=C1C(=O)OC JRQGDDUXDKCWRF-UHFFFAOYSA-M 0.000 description 1
239000004550 soluble concentrate Substances 0.000 description 1
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241000894007 species Species 0.000 description 1
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230000003068 static effect Effects 0.000 description 1
238000003860 storage Methods 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
FZMKKCQHDROFNI-UHFFFAOYSA-N sulfometuron Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 FZMKKCQHDROFNI-UHFFFAOYSA-N 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical group OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical class O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
235000013616 tea Nutrition 0.000 description 1
BCQMBFHBDZVHKU-UHFFFAOYSA-N terbumeton Chemical compound CCNC1=NC(NC(C)(C)C)=NC(OC)=N1 BCQMBFHBDZVHKU-UHFFFAOYSA-N 0.000 description 1
IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
125000000335 thiazolyl 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
SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical group CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
229960003231 thioacetazone Drugs 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
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 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
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical compound COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
230000000007 visual effect Effects 0.000 description 1
239000001993 wax Substances 0.000 description 1
238000001238 wet grinding Methods 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000002023 wood 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
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

BRPI0715451-8A 2006-07-12 2007-07-05 furil-sulfonilamino(tio)carbonil-triazolin(ti)onas substituÍdas BRPI0715451A2 (pt)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE102006032164.2		2006-07-12
DE200610032164 DE102006032164A1 (de)	2006-07-12	2006-07-12	Substituierte Furyl-sulfonylamino(thio)carbonyl-triazolin(thi)one
PCT/EP2007/005935 WO2008006499A2 (fr)	2006-07-12	2007-07-05	Furyl-sulfonylamino(thio)carbonyl-triazoline(thi)ones substituées

Publications (1)

Publication Number	Publication Date
BRPI0715451A2 true BRPI0715451A2 (pt)	2013-02-26

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BRPI0715451-8A BRPI0715451A2 (pt)	2006-07-12	2007-07-05	furil-sulfonilamino(tio)carbonil-triazolin(ti)onas substituÍdas

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Country	Link
EP (1)	EP2046781A2 (fr)
CN (1)	CN101506200A (fr)
BR (1)	BRPI0715451A2 (fr)
CA (1)	CA2657598A1 (fr)
DE (1)	DE102006032164A1 (fr)
WO (1)	WO2008006499A2 (fr)

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EP2822931B1 (fr)	2012-03-09	2017-05-03	Inception 2, Inc.	Composés de triazolone et leurs utilisations
SG11201504622PA (en)	2012-12-20	2015-07-30	Inception 2 Inc	Triazolone compounds and uses thereof
CN105579440A (zh)	2013-09-06	2016-05-11	因森普深2公司	三唑酮化合物及其应用
CN115888184B (zh) *	2022-11-10	2026-03-13	上海市精神卫生中心（上海市心理咨询培训中心）	一种用于血液镁离子检测的固相萃取装置及其应用
CN115770411B (zh) *	2022-11-10	2025-07-25	上海市精神卫生中心（上海市心理咨询培训中心）	一种键合原卟啉的镁离子固相萃取剂及其应用

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DE19540737A1 (de) *	1995-11-02	1997-05-07	Bayer Ag	Substituierte Sulfonylamino(thio)carbonylverbindungen
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

2006
- 2006-07-12 DE DE200610032164 patent/DE102006032164A1/de not_active Withdrawn
2007
- 2007-07-05 WO PCT/EP2007/005935 patent/WO2008006499A2/fr not_active Ceased
- 2007-07-05 CN CNA2007800306797A patent/CN101506200A/zh active Pending
- 2007-07-05 EP EP07765059A patent/EP2046781A2/fr not_active Withdrawn
- 2007-07-05 BR BRPI0715451-8A patent/BRPI0715451A2/pt not_active Application Discontinuation
- 2007-07-05 CA CA002657598A patent/CA2657598A1/fr not_active Abandoned

Also Published As

Publication number	Publication date
WO2008006499A8 (fr)	2008-03-06
CN101506200A (zh)	2009-08-12
DE102006032164A1 (de)	2008-01-24
WO2008006499A3 (fr)	2008-07-03
CA2657598A1 (fr)	2008-01-17
WO2008006499A2 (fr)	2008-01-17
EP2046781A2 (fr)	2009-04-15

Legal Events

Date	Code	Title	Description
2013-07-02	B11A	Dismissal acc. art.33 of ipl - examination not requested within 36 months of filing
2013-10-01	B11Y	Definitive dismissal - extension of time limit for request of examination expired [chapter 11.1.1 patent gazette]

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CA2707133C (fr)	2016-06-14	Derives chiraux de 3-(benzylsulfinyl)-5,5-dimethyl-4,5-dihydroisoxazole et de 5,5-dimethyl-3-[(1h-pyrazol-4-ylmethyl)sulfinyl]-4,5-dihydroisoxazole, procedes pour leur production et leur utilisation en tant qu'herbicides et regulateurs de croissance des vegetaux
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BR0012482B1 (pt)	2012-02-22	tien-3-il-sulfonilamino(tio)carbonil-triazolin(ti)ona s substituìdas, seu processo de preparação, composição herbicida, bem como processo para combater o crescimento indesejado de plantas.
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RU2302411C2 (ru)	2007-07-10	Замещенные арилкетоны и гербицидное средство на их основе
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TW201002207A (en)	2010-01-16	Selected salts of 3-(5,6-dihydro-1,4,2-dioxazin-3-yl)-N-[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]pyridine-2-sulfonamide, processes for their preparation and their use as herbicides and plant growth regulators
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CA2309438A1 (fr)	1999-05-14	Urees carbamoylphenylsulfoniques, leur procede de production et leur utilisation comme herbicides et regulateurs de la croissance des plantes
US20110028318A1 (en)	2011-02-03	Herbicidal compounds based on n-azinyl-n'-pyridylsulphonylureas
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AU2015203829B2 (en)	2017-02-23	2-(benzyl- and 1H-pyrazol-4-ylmethyl)sulfinyl thiazole derivatives as herbicides and plant growth regulators
BR112019020877A2 (pt)	2020-05-12	Derivados de 2-amino-5-oxialquil-pirimidina e seu uso para controlar o crescimento de plantas indesejadas
ES2349257T3 (es)	2010-12-29	Benzoilciclohexenonas sustituidas y su utilización como agentes herbicidas.
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