CA2853724A1 - Substituted 1,2,5-oxadiazole compounds and their use as herbicides - Google Patents

Substituted 1,2,5-oxadiazole compounds and their use as herbicides Download PDF

Info

Publication number: CA2853724A1
Authority: CA; Canada
Prior art keywords: alkyl; methyl; isoxazolinyl; ch2cf3; alkoxy
Prior art date: 2011-11-14
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

CA2853724A

Other languages

English (en)

French (fr)

Inventor

Helmut Kraus

Matthias Witschel

Thomas Seitz

Trevor William Newton

Liliana Parra Rapado

Raphael Aponte

Klaus Kreuz

Klaus Grossmann

Jens Lerchl

Richard R. Evans

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF SE

Original Assignee

BASF SE

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.)

2011-11-14

Filing date

2012-11-13

Publication date

2013-05-23

2012-11-13 Application filed by BASF SE filed Critical BASF SE

2013-05-23 Publication of CA2853724A1 publication Critical patent/CA2853724A1/en

Status Abandoned legal-status Critical Current

Links

150000002244 furazanes Chemical class 0.000 title abstract description 9
239000004009 herbicide Substances 0.000 title description 45
150000001875 compounds Chemical class 0.000 claims abstract description 198
229910052736 halogen Inorganic materials 0.000 claims abstract description 106
150000002367 halogens Chemical class 0.000 claims abstract description 106
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 102
239000001257 hydrogen Substances 0.000 claims abstract description 91
150000003839 salts Chemical class 0.000 claims abstract description 84
239000000203 mixture Substances 0.000 claims abstract description 64
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 63
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract description 38
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 35
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 34
125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims abstract description 32
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 29
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 23
238000000034 method Methods 0.000 claims abstract description 19
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 16
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 14
125000004648 C2-C8 alkenyl group Chemical group 0.000 claims abstract description 7
125000004649 C2-C8 alkynyl group Chemical group 0.000 claims abstract description 6
125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims abstract description 4
125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims abstract description 4
125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims abstract description 4
125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims abstract description 3
150000002431 hydrogen Chemical class 0.000 claims abstract 21
-1 1,2,5-Oxadiazole compound Chemical class 0.000 claims description 557
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 469
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 287
239000000460 chlorine Substances 0.000 claims description 101
125000001309 chloro group Chemical group Cl* 0.000 claims description 79
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 77
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 66
125000000623 heterocyclic group Chemical group 0.000 claims description 62
229910052757 nitrogen Inorganic materials 0.000 claims description 57
150000003254 radicals Chemical class 0.000 claims description 51
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 41
125000005842 heteroatom Chemical group 0.000 claims description 37
229910052731 fluorine Inorganic materials 0.000 claims description 36
229920006395 saturated elastomer Polymers 0.000 claims description 34
229910052717 sulfur Inorganic materials 0.000 claims description 34
229910052801 chlorine Inorganic materials 0.000 claims description 32
125000004433 nitrogen atom Chemical group N* 0.000 claims description 26
125000002950 monocyclic group Chemical group 0.000 claims description 24
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 20
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 20
150000001204 N-oxides Chemical class 0.000 claims description 20
JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical group F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 19
108010081348 HRT1 protein Hairy Chemical group 0.000 claims description 19
102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 19
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 17
125000000217 alkyl group Chemical group 0.000 claims description 16
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 16
239000011737 fluorine Substances 0.000 claims description 15
229910052760 oxygen Inorganic materials 0.000 claims description 14
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 13
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 12
125000002619 bicyclic group Chemical group 0.000 claims description 11
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 9
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
238000006467 substitution reaction Methods 0.000 claims description 7
125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 6
125000003971 isoxazolinyl group Chemical group 0.000 claims description 6
125000000842 isoxazolyl group Chemical group 0.000 claims description 6
125000004122 cyclic group Chemical group 0.000 claims description 5
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
125000005844 heterocyclyloxy group Chemical group 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 2
125000005879 dioxolanyl group Chemical group 0.000 claims description 2
125000002541 furyl group Chemical group 0.000 claims description 2
125000002757 morpholinyl group Chemical group 0.000 claims description 2
125000002971 oxazolyl group Chemical group 0.000 claims description 2
125000004193 piperazinyl group Chemical group 0.000 claims description 2
125000003386 piperidinyl group Chemical group 0.000 claims description 2
125000003373 pyrazinyl group Chemical group 0.000 claims description 2
125000003226 pyrazolyl group Chemical group 0.000 claims description 2
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
125000000335 thiazolyl group Chemical group 0.000 claims description 2
125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 1
125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
ICJSJAJWTWPSBD-UHFFFAOYSA-N cloquintocet Chemical compound C1=CN=C2C(OCC(=O)O)=CC=C(Cl)C2=C1 ICJSJAJWTWPSBD-UHFFFAOYSA-N 0.000 description 143
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 description 142
PFJJMJDEVDLPNE-UHFFFAOYSA-N Benoxacor Chemical compound C1=CC=C2N(C(=O)C(Cl)Cl)C(C)COC2=C1 PFJJMJDEVDLPNE-UHFFFAOYSA-N 0.000 description 142
ITGSCCPVERXFGN-UHFFFAOYSA-N isoxadifen Chemical compound C1C(C(=O)O)=NOC1(C=1C=CC=CC=1)C1=CC=CC=C1 ITGSCCPVERXFGN-UHFFFAOYSA-N 0.000 description 142
XEJNEDVTJPXRSM-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-5-methyl-4,5-dihydro-1H-pyrazole-3,5-dicarboxylic acid Chemical compound OC(=O)C1(C)CC(C(O)=O)=NN1C1=CC=C(Cl)C=C1Cl XEJNEDVTJPXRSM-UHFFFAOYSA-N 0.000 description 139
YRMLFORXOOIJDR-UHFFFAOYSA-N Dichlormid Chemical compound ClC(Cl)C(=O)N(CC=C)CC=C YRMLFORXOOIJDR-UHFFFAOYSA-N 0.000 description 137
239000005562 Glyphosate Substances 0.000 description 124
XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 108
229940097068 glyphosate Drugs 0.000 description 108
239000005591 Pendimethalin Substances 0.000 description 92
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 92
235000013350 formula milk Nutrition 0.000 description 89
239000005621 Terbuthylazine Substances 0.000 description 63
FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 63
239000005507 Diflufenican Substances 0.000 description 57
WYEHFWKAOXOVJD-UHFFFAOYSA-N diflufenican Chemical compound FC1=CC(F)=CC=C1NC(=O)C1=CC=CN=C1OC1=CC=CC(C(F)(F)F)=C1 WYEHFWKAOXOVJD-UHFFFAOYSA-N 0.000 description 57
150000002148 esters Chemical group 0.000 description 52
239000005580 Metazachlor Substances 0.000 description 50
MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 50
STEPQTYSZVCJPV-UHFFFAOYSA-N metazachlor Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)CN1N=CC=C1 STEPQTYSZVCJPV-UHFFFAOYSA-N 0.000 description 50
125000004432 carbon atom Chemical group C* 0.000 description 43
230000002363 herbicidal effect Effects 0.000 description 43
IYMLUHWAJFXAQP-UHFFFAOYSA-N topramezone Chemical compound CC1=C(C(=O)C2=C(N(C)N=C2)O)C=CC(S(C)(=O)=O)=C1C1=NOCC1 IYMLUHWAJFXAQP-UHFFFAOYSA-N 0.000 description 42
239000005578 Mesotrione Substances 0.000 description 36
239000005586 Nicosulfuron Substances 0.000 description 36
KPUREKXXPHOJQT-UHFFFAOYSA-N mesotrione Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O KPUREKXXPHOJQT-UHFFFAOYSA-N 0.000 description 36
RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 description 36
239000005620 Tembotrione Substances 0.000 description 33
IUQAXCIUEPFPSF-UHFFFAOYSA-N tembotrione Chemical compound ClC1=C(COCC(F)(F)F)C(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O IUQAXCIUEPFPSF-UHFFFAOYSA-N 0.000 description 33
241000196324 Embryophyta Species 0.000 description 29
244000038559 crop plants Species 0.000 description 24
CASLETQIYIQFTQ-UHFFFAOYSA-N 3-[[5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)pyrazol-4-yl]methylsulfonyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound CN1N=C(C(F)(F)F)C(CS(=O)(=O)C=2CC(C)(C)ON=2)=C1OC(F)F CASLETQIYIQFTQ-UHFFFAOYSA-N 0.000 description 22
239000005607 Pyroxsulam Substances 0.000 description 22
GLBLPMUBLHYFCW-UHFFFAOYSA-N n-(5,7-dimethoxy-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-2-methoxy-4-(trifluoromethyl)pyridine-3-sulfonamide Chemical compound N1=C2N=C(OC)C=C(OC)N2N=C1NS(=O)(=O)C1=C(OC)N=CC=C1C(F)(F)F GLBLPMUBLHYFCW-UHFFFAOYSA-N 0.000 description 22
JKPSVOHVUGMYGH-UHFFFAOYSA-M sodium;(4,6-dimethoxypyrimidin-2-yl)-[[3-methoxycarbonyl-6-(trifluoromethyl)pyridin-2-yl]sulfonylcarbamoyl]azanide Chemical compound [Na+].COC(=O)C1=CC=C(C(F)(F)F)N=C1S(=O)(=O)NC(=O)[N-]C1=NC(OC)=CC(OC)=N1 JKPSVOHVUGMYGH-UHFFFAOYSA-M 0.000 description 22
239000005597 Pinoxaden Substances 0.000 description 21
JBDHZKLJNAIJNC-LLVKDONJSA-N clodinafop-propargyl Chemical group C1=CC(O[C@H](C)C(=O)OCC#C)=CC=C1OC1=NC=C(Cl)C=C1F JBDHZKLJNAIJNC-LLVKDONJSA-N 0.000 description 21
PQKBPHSEKWERTG-LLVKDONJSA-N ethyl (2r)-2-[4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy]propanoate Chemical group C1=CC(O[C@H](C)C(=O)OCC)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 PQKBPHSEKWERTG-LLVKDONJSA-N 0.000 description 21
MGOHCFMYLBAPRN-UHFFFAOYSA-N pinoxaden Chemical compound CCC1=CC(C)=CC(CC)=C1C(C1=O)=C(OC(=O)C(C)(C)C)N2N1CCOCC2 MGOHCFMYLBAPRN-UHFFFAOYSA-N 0.000 description 21
IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 description 19
239000003053 toxin Substances 0.000 description 19
231100000765 toxin Toxicity 0.000 description 19
108700012359 toxins Proteins 0.000 description 19
239000003112 inhibitor Substances 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
229910052794 bromium Inorganic materials 0.000 description 16
RUCAXVJJQQJZGU-UHFFFAOYSA-M hydron;2-(phosphonatomethylamino)acetate;trimethylsulfanium Chemical compound C[S+](C)C.OP(O)(=O)CNCC([O-])=O RUCAXVJJQQJZGU-UHFFFAOYSA-M 0.000 description 16
229910052702 rhenium Inorganic materials 0.000 description 16
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 description 15
239000005499 Clomazone Substances 0.000 description 15
RXCPQSJAVKGONC-UHFFFAOYSA-N Flumetsulam Chemical compound N1=C2N=C(C)C=CN2N=C1S(=O)(=O)NC1=C(F)C=CC=C1F RXCPQSJAVKGONC-UHFFFAOYSA-N 0.000 description 15
239000005560 Foramsulfuron Substances 0.000 description 15
XVOKUMIPKHGGTN-UHFFFAOYSA-N Imazethapyr Chemical compound OC(=O)C1=CC(CC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 XVOKUMIPKHGGTN-UHFFFAOYSA-N 0.000 description 15
239000005583 Metribuzin Substances 0.000 description 15
KIEDNEWSYUYDSN-UHFFFAOYSA-N clomazone Chemical compound O=C1C(C)(C)CON1CC1=CC=CC=C1Cl KIEDNEWSYUYDSN-UHFFFAOYSA-N 0.000 description 15
FOUWCSDKDDHKQP-UHFFFAOYSA-N flumioxazin Chemical compound FC1=CC=2OCC(=O)N(CC#C)C=2C=C1N(C1=O)C(=O)C2=C1CCCC2 FOUWCSDKDDHKQP-UHFFFAOYSA-N 0.000 description 15
PXDNXJSDGQBLKS-UHFFFAOYSA-N foramsulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=C(NC=O)C=2)C(=O)N(C)C)=N1 PXDNXJSDGQBLKS-UHFFFAOYSA-N 0.000 description 15
238000009472 formulation Methods 0.000 description 15
FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 description 15
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 15
239000002253 acid Substances 0.000 description 14
NIFKBBMCXCMCAO-UHFFFAOYSA-N methyl 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-4-(methanesulfonamidomethyl)benzoate Chemical group COC(=O)C1=CC=C(CNS(C)(=O)=O)C=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 NIFKBBMCXCMCAO-UHFFFAOYSA-N 0.000 description 14
239000000049 pigment Substances 0.000 description 14
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 14
108090000623 proteins and genes Proteins 0.000 description 13
239000005561 Glufosinate Substances 0.000 description 11
102000004169 proteins and genes Human genes 0.000 description 11
229910052703 rhodium Inorganic materials 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
240000008042 Zea mays Species 0.000 description 10
238000010790 dilution Methods 0.000 description 10
239000012895 dilution Substances 0.000 description 10
150000003852 triazoles Chemical class 0.000 description 10
NUPJIGQFXCQJBK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-5-(methoxymethyl)nicotinic acid Chemical compound OC(=O)C1=CC(COC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 NUPJIGQFXCQJBK-UHFFFAOYSA-N 0.000 description 9
239000005566 Imazamox Substances 0.000 description 9
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 9
235000002017 Zea mays subsp mays Nutrition 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
235000005822 corn Nutrition 0.000 description 9
239000002270 dispersing agent Substances 0.000 description 9
239000003921 oil Substances 0.000 description 9
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 description 9
GNHDVXLWBQYPJE-UHFFFAOYSA-N saflufenacil Chemical compound C1=C(Cl)C(C(=O)NS(=O)(=O)N(C)C(C)C)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F GNHDVXLWBQYPJE-UHFFFAOYSA-N 0.000 description 9
239000007787 solid Substances 0.000 description 9
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 8
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 description 8
239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 8
CLQMBPJKHLGMQK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)nicotinic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC=CC=C1C(O)=O CLQMBPJKHLGMQK-UHFFFAOYSA-N 0.000 description 8
MAYMYMXYWIVVOK-UHFFFAOYSA-N 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-4-(methanesulfonamidomethyl)benzoic acid Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=C(CNS(C)(=O)=O)C=2)C(O)=O)=N1 MAYMYMXYWIVVOK-UHFFFAOYSA-N 0.000 description 8
KRQUFUKTQHISJB-YYADALCUSA-N 2-[(E)-N-[2-(4-chlorophenoxy)propoxy]-C-propylcarbonimidoyl]-3-hydroxy-5-(thian-3-yl)cyclohex-2-en-1-one Chemical compound CCC\C(=N/OCC(C)OC1=CC=C(Cl)C=C1)C1=C(O)CC(CC1=O)C1CCCSC1 KRQUFUKTQHISJB-YYADALCUSA-N 0.000 description 8
IRJQWZWMQCVOLA-ZBKNUEDVSA-N 2-[(z)-n-[(3,5-difluorophenyl)carbamoylamino]-c-methylcarbonimidoyl]pyridine-3-carboxylic acid Chemical compound N=1C=CC=C(C(O)=O)C=1C(/C)=N\NC(=O)NC1=CC(F)=CC(F)=C1 IRJQWZWMQCVOLA-ZBKNUEDVSA-N 0.000 description 8
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 description 8
IOYNQIMAUDJVEI-ZFNPBRLTSA-N 2-[N-[(E)-3-chloroprop-2-enoxy]-C-ethylcarbonimidoyl]-3-hydroxy-5-(oxan-4-yl)cyclohex-2-en-1-one Chemical compound C1C(=O)C(C(=NOC\C=C\Cl)CC)=C(O)CC1C1CCOCC1 IOYNQIMAUDJVEI-ZFNPBRLTSA-N 0.000 description 8
UFAPVJDEYHLLBG-UHFFFAOYSA-N 2-{2-chloro-4-(methylsulfonyl)-3-[(tetrahydrofuran-2-ylmethoxy)methyl]benzoyl}cyclohexane-1,3-dione Chemical compound ClC1=C(COCC2OCCC2)C(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O UFAPVJDEYHLLBG-UHFFFAOYSA-N 0.000 description 8
XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 8
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150000003624 transition metals Chemical class 0.000 description 1
238000013519 translation Methods 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
150000003918 triazines Chemical class 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
YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-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
AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical group 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
238000001665 trituration Methods 0.000 description 1
239000002753 trypsin inhibitor Substances 0.000 description 1
150000004669 very long chain fatty acids Chemical class 0.000 description 1
244000052613 viral pathogen Species 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
239000002699 waste material Substances 0.000 description 1
239000003021 water soluble solvent Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1
239000000230 xanthan gum Substances 0.000 description 1
229920001285 xanthan gum Polymers 0.000 description 1
235000010493 xanthan gum Nutrition 0.000 description 1
229940082509 xanthan gum Drugs 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- 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
- A01N43/82—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 three ring hetero atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/08—1,2,5-Oxadiazoles; Hydrogenated 1,2,5-oxadiazoles
- 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
- C07D413/12—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 chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

CA2853724A 2011-11-14 2012-11-13 Substituted 1,2,5-oxadiazole compounds and their use as herbicides Abandoned CA2853724A1 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US201161559164P	2011-11-14	2011-11-14
US61/559,164		2011-11-14
PCT/EP2012/072469 WO2013072300A1 (en)	2011-11-14	2012-11-13	Substituted 1,2,5-oxadiazole compounds and their use as herbicides

Publications (1)

Publication Number	Publication Date
CA2853724A1 true CA2853724A1 (en)	2013-05-23

Family

ID=47146426

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA2853724A Abandoned CA2853724A1 (en)	2011-11-14	2012-11-13	Substituted 1,2,5-oxadiazole compounds and their use as herbicides

Country Status (17)

Country	Link
US (1)	US20140323306A1 (2)
EP (1)	EP2780334A1 (2)
JP (1)	JP2014533254A (2)
KR (1)	KR20140098134A (2)
CN (1)	CN104039770A (2)
AR (1)	AR088857A1 (2)
AU (1)	AU2012338953A1 (2)
BR (1)	BR112014011534A2 (2)
CA (1)	CA2853724A1 (2)
CO (1)	CO6950497A2 (2)
CR (1)	CR20140195A (2)
EA (1)	EA201400576A1 (2)
IL (1)	IL232235A0 (2)
IN (1)	IN2014CN03268A (2)
MX (1)	MX2014005175A (2)
WO (1)	WO2013072300A1 (2)
ZA (1)	ZA201404294B (2)

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2012
- 2012-11-13 AR ARP120104276A patent/AR088857A1/es unknown
- 2012-11-13 CA CA2853724A patent/CA2853724A1/en not_active Abandoned
- 2012-11-13 EP EP12783624.5A patent/EP2780334A1/en not_active Withdrawn
- 2012-11-13 KR KR1020147016251A patent/KR20140098134A/ko not_active Withdrawn
- 2012-11-13 CN CN201280067032.2A patent/CN104039770A/zh active Pending
- 2012-11-13 US US14/357,897 patent/US20140323306A1/en not_active Abandoned
- 2012-11-13 IN IN3268CHN2014 patent/IN2014CN03268A/en unknown
- 2012-11-13 MX MX2014005175A patent/MX2014005175A/es unknown
- 2012-11-13 WO PCT/EP2012/072469 patent/WO2013072300A1/en not_active Ceased
- 2012-11-13 BR BR112014011534A patent/BR112014011534A2/pt not_active IP Right Cessation
- 2012-11-13 JP JP2014540513A patent/JP2014533254A/ja active Pending
- 2012-11-13 AU AU2012338953A patent/AU2012338953A1/en not_active Abandoned
- 2012-11-13 EA EA201400576A patent/EA201400576A1/ru unknown
2014
- 2014-04-24 IL IL232235A patent/IL232235A0/en unknown
- 2014-04-29 CR CR20140195A patent/CR20140195A/es unknown
- 2014-05-08 CO CO14099141A patent/CO6950497A2/es unknown
- 2014-06-11 ZA ZA2014/04294A patent/ZA201404294B/en unknown

Also Published As

Publication number	Publication date
CO6950497A2 (es)	2014-05-20
ZA201404294B (en)	2017-11-29
CN104039770A (zh)	2014-09-10
EP2780334A1 (en)	2014-09-24
EA201400576A1 (ru)	2014-11-28
JP2014533254A (ja)	2014-12-11
IL232235A0 (en)	2014-06-30
US20140323306A1 (en)	2014-10-30
WO2013072300A1 (en)	2013-05-23
CR20140195A (es)	2014-06-03
BR112014011534A2 (pt)	2017-05-09
AR088857A1 (es)	2014-07-10
IN2014CN03268A (2)	2015-07-03
KR20140098134A (ko)	2014-08-07
AU2012338953A1 (en)	2014-06-05
MX2014005175A (es)	2014-05-28

Legal Events

Date	Code	Title	Description
2016-12-26	FZDE	Discontinued	Effective date: 20161114

Publication	Publication Date	Title
EP3022190B1 (en)	2017-06-28	N-(1,2,4-triazol-3-yl)-pyridin-2-yl-carboxamide derivatives as herbicides
US9902704B2 (en)	2018-02-27	Substituted N-(tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxamide compounds and their use as herbicides
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AU2014267561B2 (en)	2018-06-07	Substituted N-(tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxamide compounds and their use as herbicides
EP3390372B1 (en)	2020-06-03	Benzamide compounds and their use as herbicides
CA2853724A1 (en)	2013-05-23	Substituted 1,2,5-oxadiazole compounds and their use as herbicides
US20160280696A1 (en)	2016-09-29	Substituted 1,2,5-oxadiazole compounds and their use as herbicides
US9398768B2 (en)	2016-07-26	Substituted N-(tetrazol-5-yl)- and N-(triazol-5-yl)pyridin-3-yl-carboxamide compounds and their use as herbicides
WO2014184015A1 (en)	2014-11-20	Substituted n-(tetrazol-5-yl)- and n-(triazol-5-yl)arylcarboxamide compounds and their use as herbicides
AU2012338879A1 (en)	2014-06-05	Substituted 1,2,5-oxadiazole compounds and their use as herbicides II
WO2014184074A1 (en)	2014-11-20	Substituted n-(tetrazol-5-yl)- and n-(triazol-5-yl)hetarylcarboxamide compounds and their use as herbicides
AU2012338748A1 (en)	2014-06-05	Substituted 1,2,5-oxadiazole compounds and their use as herbicides III
US20150291570A1 (en)	2015-10-15	Substituted N-(tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxamide compounds and their use as herbicides
WO2014184014A1 (en)	2014-11-20	N-(1,2,5-oxadiazol-3-yl)carboxamide compounds and their use as herbicides
WO2014184073A1 (en)	2014-11-20	Substituted n-(tetrazol-5-yl)- and n-(triazol-5-yl)arylcarboxamide compounds and their use as herbicides
WO2014184017A1 (en)	2014-11-20	Substituted n-(tetrazol-5-yl)- and n-(triazol-5-yl)pyridin-3-yl-carboxamide compounds and their use as herbicides
WO2014184058A1 (en)	2014-11-20	Substituted 1,2,5-oxadiazole compounds and their use as herbicides
EP2907807A1 (en)	2015-08-19	Benzamide compounds and their use as herbicides