CN107250127A - 除草化合物 - Google Patents
除草化合物 Download PDFInfo
- Publication number
- CN107250127A CN107250127A CN201680009376.6A CN201680009376A CN107250127A CN 107250127 A CN107250127 A CN 107250127A CN 201680009376 A CN201680009376 A CN 201680009376A CN 107250127 A CN107250127 A CN 107250127A
- Authority
- CN
- China
- Prior art keywords
- alkyl
- methyl
- chemical formula
- group
- alkoxy
- Prior art date
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 149
- 239000004009 herbicide Substances 0.000 title claims description 21
- 239000000203 mixture Substances 0.000 claims abstract description 75
- 241000196324 Embryophyta Species 0.000 claims abstract description 65
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 20
- 150000003217 pyrazoles Chemical class 0.000 claims abstract description 12
- 244000038559 crop plants Species 0.000 claims abstract description 11
- 230000008635 plant growth Effects 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims description 146
- -1 C1-C6Alkyl Chemical group 0.000 claims description 141
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 51
- 244000025254 Cannabis sativa Species 0.000 claims description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 30
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 29
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 150000002367 halogens Chemical class 0.000 claims description 29
- 238000002360 preparation method Methods 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 27
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 26
- 239000011737 fluorine Substances 0.000 claims description 26
- 229910052731 fluorine Inorganic materials 0.000 claims description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 25
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 20
- 239000005864 Sulphur Substances 0.000 claims description 20
- 150000001412 amines Chemical class 0.000 claims description 20
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 19
- 239000000460 chlorine Substances 0.000 claims description 19
- 229910052801 chlorine Inorganic materials 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 17
- 150000002148 esters Chemical class 0.000 claims description 17
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 16
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 239000011734 sodium Substances 0.000 claims description 14
- 229910052708 sodium Inorganic materials 0.000 claims description 14
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 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 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- 125000004122 cyclic group Chemical group 0.000 claims description 11
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 10
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- RMFGNMMNUZWCRZ-UHFFFAOYSA-N Humulone Natural products CC(C)CC(=O)C1=C(O)C(O)(CC=C(C)C)C(O)=C(CC=C(C)C)C1=O RMFGNMMNUZWCRZ-UHFFFAOYSA-N 0.000 claims description 8
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 8
- VMSLCPKYRPDHLN-NRFANRHFSA-N humulone Chemical compound CC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C(O)[C@@](O)(CC=C(C)C)C1=O VMSLCPKYRPDHLN-NRFANRHFSA-N 0.000 claims description 8
- 150000002924 oxiranes Chemical class 0.000 claims description 8
- 239000000575 pesticide Substances 0.000 claims description 8
- 235000019260 propionic acid Nutrition 0.000 claims description 8
- 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 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 7
- 239000002671 adjuvant Substances 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- 150000002576 ketones Chemical class 0.000 claims description 7
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims description 6
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 6
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 235000021307 Triticum Nutrition 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims description 6
- 150000003254 radicals Chemical class 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 5
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 235000013339 cereals Nutrition 0.000 claims description 5
- 125000004494 ethyl ester group Chemical group 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 239000011630 iodine Substances 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- UDPGUMQDCGORJQ-UHFFFAOYSA-N (2-chloroethyl)phosphonic acid Chemical compound OP(O)(=O)CCCl UDPGUMQDCGORJQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 125000006765 (C2-C6) haloalkenyloxy group Chemical group 0.000 claims description 4
- 239000005630 Diquat Substances 0.000 claims description 4
- 239000005562 Glyphosate Substances 0.000 claims description 4
- 235000010086 Setaria viridis var. viridis Nutrition 0.000 claims description 4
- 150000003851 azoles Chemical class 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- MXZACTZQSGYANA-UHFFFAOYSA-N chembl545463 Chemical compound Cl.C1=CC(OC)=CC=C1C(N=C1)=CN2C1=NC(C)=C2O MXZACTZQSGYANA-UHFFFAOYSA-N 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- JLYFCTQDENRSOL-UHFFFAOYSA-N 2-chloro-N-(2,4-dimethylthiophen-3-yl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound COCC(C)N(C(=O)CCl)C=1C(C)=CSC=1C JLYFCTQDENRSOL-UHFFFAOYSA-N 0.000 claims description 3
- JDWQITFHZOBBFE-UHFFFAOYSA-N Benzofenap Chemical compound C=1C=C(Cl)C(C)=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OCC(=O)C1=CC=C(C)C=C1 JDWQITFHZOBBFE-UHFFFAOYSA-N 0.000 claims description 3
- MNFMIVVPXOGUMX-UHFFFAOYSA-N Fluchloralin Chemical compound CCCN(CCCl)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O MNFMIVVPXOGUMX-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- CNILNQMBAHKMFS-UHFFFAOYSA-M Pyrithiobac-sodium Chemical compound [Na+].COC1=CC(OC)=NC(SC=2C(=C(Cl)C=CC=2)C([O-])=O)=N1 CNILNQMBAHKMFS-UHFFFAOYSA-M 0.000 claims description 3
- 150000001336 alkenes Chemical class 0.000 claims description 3
- 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 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 238000009826 distribution Methods 0.000 claims description 3
- 239000003205 fragrance Substances 0.000 claims description 3
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims description 3
- 229940097068 glyphosate Drugs 0.000 claims description 3
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims description 3
- 150000002916 oxazoles Chemical class 0.000 claims description 3
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 239000010902 straw Substances 0.000 claims description 3
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000006717 (C3-C10) cycloalkenyl group Chemical group 0.000 claims description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 2
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 2
- 239000002794 2,4-DB Substances 0.000 claims description 2
- YIVXMZJTEQBPQO-UHFFFAOYSA-N 2,4-DB Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1Cl YIVXMZJTEQBPQO-UHFFFAOYSA-N 0.000 claims description 2
- YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- YUVKUEAFAVKILW-UHFFFAOYSA-N 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 YUVKUEAFAVKILW-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 claims description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 claims description 2
- NYRMIJKDBAQCHC-UHFFFAOYSA-N 5-(methylamino)-2-phenyl-4-[3-(trifluoromethyl)phenyl]furan-3(2H)-one Chemical compound O1C(NC)=C(C=2C=C(C=CC=2)C(F)(F)F)C(=O)C1C1=CC=CC=C1 NYRMIJKDBAQCHC-UHFFFAOYSA-N 0.000 claims description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 2
- NXQDBZGWYSEGFL-UHFFFAOYSA-N Anilofos Chemical compound COP(=S)(OC)SCC(=O)N(C(C)C)C1=CC=C(Cl)C=C1 NXQDBZGWYSEGFL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005470 Beflubutamid Substances 0.000 claims description 2
- 239000005471 Benfluralin Substances 0.000 claims description 2
- 239000005484 Bifenox Substances 0.000 claims description 2
- KZCBXHSWMMIEQU-UHFFFAOYSA-N Chlorthal Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(C(O)=O)C(Cl)=C1Cl KZCBXHSWMMIEQU-UHFFFAOYSA-N 0.000 claims description 2
- NPOJQCVWMSKXDN-UHFFFAOYSA-N Dacthal Chemical compound COC(=O)C1=C(Cl)C(Cl)=C(C(=O)OC)C(Cl)=C1Cl NPOJQCVWMSKXDN-UHFFFAOYSA-N 0.000 claims description 2
- NNYRZQHKCHEXSD-UHFFFAOYSA-N Daimuron Chemical compound C1=CC(C)=CC=C1NC(=O)NC(C)(C)C1=CC=CC=C1 NNYRZQHKCHEXSD-UHFFFAOYSA-N 0.000 claims description 2
- 239000005503 Desmedipham Substances 0.000 claims description 2
- LBGPXIPGGRQBJW-UHFFFAOYSA-N Difenzoquat Chemical compound C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 LBGPXIPGGRQBJW-UHFFFAOYSA-N 0.000 claims description 2
- OFDYMSKSGFSLLM-UHFFFAOYSA-N Dinitramine Chemical compound CCN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C(N)=C1[N+]([O-])=O OFDYMSKSGFSLLM-UHFFFAOYSA-N 0.000 claims description 2
- 239000005510 Diuron Substances 0.000 claims description 2
- GUVLYNGULCJVDO-UHFFFAOYSA-N EPTC Chemical compound CCCN(CCC)C(=O)SCC GUVLYNGULCJVDO-UHFFFAOYSA-N 0.000 claims description 2
- 244000058871 Echinochloa crus-galli Species 0.000 claims description 2
- 239000005976 Ethephon Substances 0.000 claims description 2
- 239000005514 Flazasulfuron Substances 0.000 claims description 2
- HWATZEJQIXKWQS-UHFFFAOYSA-N Flazasulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(F)(F)F)=N1 HWATZEJQIXKWQS-UHFFFAOYSA-N 0.000 claims description 2
- 239000005533 Fluometuron Substances 0.000 claims description 2
- 239000005559 Flurtamone Substances 0.000 claims description 2
- 239000005566 Imazamox Substances 0.000 claims description 2
- SUSRORUBZHMPCO-UHFFFAOYSA-N MC-4379 Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 SUSRORUBZHMPCO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005577 Mesosulfuron Substances 0.000 claims description 2
- FFQPZWRNXKPNPX-UHFFFAOYSA-N N-benzyl-2-[4-fluoro-3-(trifluoromethyl)phenoxy]butanamide Chemical compound C=1C=CC=CC=1CNC(=O)C(CC)OC1=CC=C(F)C(C(F)(F)F)=C1 FFQPZWRNXKPNPX-UHFFFAOYSA-N 0.000 claims description 2
- AQGDXJQRVOCUQX-UHFFFAOYSA-N N.[S] Chemical compound N.[S] AQGDXJQRVOCUQX-UHFFFAOYSA-N 0.000 claims description 2
- NYRSPHPCSCVZJI-UHFFFAOYSA-N NNC(=O)N=N.C1=CC=CC=C1 Chemical class NNC(=O)N=N.C1=CC=CC=C1 NYRSPHPCSCVZJI-UHFFFAOYSA-N 0.000 claims description 2
- 239000005642 Oleic acid Substances 0.000 claims description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000005595 Picloram Substances 0.000 claims description 2
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 claims description 2
- IHHMUBRVTJMLQO-UHFFFAOYSA-N Pyraclonil Chemical compound C#CCN(C)C1=C(C#N)C=NN1C1=NN(CCCC2)C2=C1Cl IHHMUBRVTJMLQO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005625 Tri-allate Substances 0.000 claims description 2
- MWBPRDONLNQCFV-UHFFFAOYSA-N Tri-allate Chemical compound CC(C)N(C(C)C)C(=O)SCC(Cl)=C(Cl)Cl MWBPRDONLNQCFV-UHFFFAOYSA-N 0.000 claims description 2
- VYOZKLLJJHRFNA-UHFFFAOYSA-N [F].N Chemical compound [F].N VYOZKLLJJHRFNA-UHFFFAOYSA-N 0.000 claims description 2
- WHDHEVMINMZADQ-UHFFFAOYSA-N [F].N1C=CC=C1 Chemical compound [F].N1C=CC=C1 WHDHEVMINMZADQ-UHFFFAOYSA-N 0.000 claims description 2
- INJDDZZBIUHKQX-UHFFFAOYSA-N [P].C(CCC)N Chemical compound [P].C(CCC)N INJDDZZBIUHKQX-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 150000001345 alkine derivatives Chemical class 0.000 claims description 2
- SMDHCQAYESWHAE-UHFFFAOYSA-N benfluralin Chemical compound CCCCN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O SMDHCQAYESWHAE-UHFFFAOYSA-N 0.000 claims description 2
- XLTRGZZLGXNXGD-UHFFFAOYSA-N benzene;1h-pyrazole Chemical class C=1C=NNC=1.C1=CC=CC=C1 XLTRGZZLGXNXGD-UHFFFAOYSA-N 0.000 claims description 2
- 125000005605 benzo group Chemical group 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- GINJFDRNADDBIN-FXQIFTODSA-N bilanafos Chemical compound OC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](N)CCP(C)(O)=O GINJFDRNADDBIN-FXQIFTODSA-N 0.000 claims description 2
- CURLHBZYTFVCRG-UHFFFAOYSA-N butan-2-yl n-(3-chlorophenyl)carbamate Chemical compound CCC(C)OC(=O)NC1=CC=CC(Cl)=C1 CURLHBZYTFVCRG-UHFFFAOYSA-N 0.000 claims description 2
- YALMXYPQBUJUME-UHFFFAOYSA-L calcium chlorate Chemical compound [Ca+2].[O-]Cl(=O)=O.[O-]Cl(=O)=O YALMXYPQBUJUME-UHFFFAOYSA-L 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- WZJZMXBKUWKXTQ-UHFFFAOYSA-N desmedipham Chemical compound CCOC(=O)NC1=CC=CC(OC(=O)NC=2C=CC=CC=2)=C1 WZJZMXBKUWKXTQ-UHFFFAOYSA-N 0.000 claims description 2
- OGGXGZAMXPVRFZ-UHFFFAOYSA-N dimethylarsinic acid Chemical compound C[As](C)(O)=O OGGXGZAMXPVRFZ-UHFFFAOYSA-N 0.000 claims description 2
- OSUHJPCHFDQAIT-UHFFFAOYSA-N ethyl 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoate Chemical group C1=CC(OC(C)C(=O)OCC)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 OSUHJPCHFDQAIT-UHFFFAOYSA-N 0.000 claims description 2
- 229960004979 fampridine Drugs 0.000 claims description 2
- 239000011790 ferrous sulphate Substances 0.000 claims description 2
- 235000003891 ferrous sulphate Nutrition 0.000 claims description 2
- RZILCCPWPBTYDO-UHFFFAOYSA-N fluometuron Chemical compound CN(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 RZILCCPWPBTYDO-UHFFFAOYSA-N 0.000 claims description 2
- 150000007857 hydrazones Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 150000002460 imidazoles Chemical class 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- NRXQIUSYPAHGNM-UHFFFAOYSA-N ioxynil Chemical compound OC1=C(I)C=C(C#N)C=C1I NRXQIUSYPAHGNM-UHFFFAOYSA-N 0.000 claims description 2
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 claims description 2
- 229910000359 iron(II) sulfate Inorganic materials 0.000 claims description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- QYPPRTNMGCREIM-UHFFFAOYSA-N methylarsonic acid Chemical compound C[As](O)(O)=O QYPPRTNMGCREIM-UHFFFAOYSA-N 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 229960002939 metizoline Drugs 0.000 claims description 2
- NVGOPFQZYCNLDU-UHFFFAOYSA-N norflurazon Chemical compound O=C1C(Cl)=C(NC)C=NN1C1=CC=CC(C(F)(F)F)=C1 NVGOPFQZYCNLDU-UHFFFAOYSA-N 0.000 claims description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 2
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- NQQVFXUMIDALNH-UHFFFAOYSA-N picloram Chemical compound NC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl NQQVFXUMIDALNH-UHFFFAOYSA-N 0.000 claims description 2
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 claims description 2
- FKERUJTUOYLBKB-UHFFFAOYSA-N pyrazoxyfen Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OCC(=O)C1=CC=CC=C1 FKERUJTUOYLBKB-UHFFFAOYSA-N 0.000 claims description 2
- 235000010339 sodium tetraborate Nutrition 0.000 claims description 2
- 150000003457 sulfones Chemical class 0.000 claims description 2
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 claims description 2
- GYICYQJEVCIYJY-UHFFFAOYSA-N thiophen-1-ylidenemethanone Chemical compound O=C=S1C=CC=C1 GYICYQJEVCIYJY-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 12
- 239000005584 Metsulfuron-methyl Substances 0.000 claims 3
- ZBMRKNMTMPPMMK-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid;azane Chemical compound [NH4+].CP(O)(=O)CCC(N)C([O-])=O ZBMRKNMTMPPMMK-UHFFFAOYSA-N 0.000 claims 2
- 239000005472 Bensulfuron methyl Substances 0.000 claims 2
- 239000005564 Halosulfuron methyl Substances 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 claims 2
- 239000005605 Pyraflufen-ethyl Substances 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- XMQFTWRPUQYINF-UHFFFAOYSA-N bensulfuron-methyl Chemical group COC(=O)C1=CC=CC=C1CS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 XMQFTWRPUQYINF-UHFFFAOYSA-N 0.000 claims 2
- FUHMZYWBSHTEDZ-UHFFFAOYSA-M bispyribac-sodium Chemical compound [Na+].COC1=CC(OC)=NC(OC=2C(=C(OC=3N=C(OC)C=C(OC)N=3)C=CC=2)C([O-])=O)=N1 FUHMZYWBSHTEDZ-UHFFFAOYSA-M 0.000 claims 2
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 claims 2
- GXEKYRXVRROBEV-FBXFSONDSA-N (1r,2s,3r,4s)-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid Chemical compound C1C[C@@H]2[C@@H](C(O)=O)[C@@H](C(=O)O)[C@H]1O2 GXEKYRXVRROBEV-FBXFSONDSA-N 0.000 claims 1
- IPPAUTOBDWNELX-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl) 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate Chemical group C1=C([N+]([O-])=O)C(C(=O)OCC(=O)OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 IPPAUTOBDWNELX-UHFFFAOYSA-N 0.000 claims 1
- XJPOOEMIUDHWSO-PHIMTYICSA-N (2s,5r)-2,5-dimethyl-n-phenylpyrrolidine-1-carboxamide Chemical compound C[C@H]1CC[C@@H](C)N1C(=O)NC1=CC=CC=C1 XJPOOEMIUDHWSO-PHIMTYICSA-N 0.000 claims 1
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 1
- GAWAYYRQGQZKCR-REOHCLBHSA-N (S)-2-chloropropanoic acid Chemical compound C[C@H](Cl)C(O)=O GAWAYYRQGQZKCR-REOHCLBHSA-N 0.000 claims 1
- OVXMBIVWNJDDSM-UHFFFAOYSA-N (benzhydrylideneamino) 2,6-bis[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate Chemical compound COC1=CC(OC)=NC(OC=2C(=C(OC=3N=C(OC)C=C(OC)N=3)C=CC=2)C(=O)ON=C(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 OVXMBIVWNJDDSM-UHFFFAOYSA-N 0.000 claims 1
- XQEMNBNCQVQXMO-UHFFFAOYSA-M 1,2-dimethyl-3,5-diphenylpyrazol-1-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 XQEMNBNCQVQXMO-UHFFFAOYSA-M 0.000 claims 1
- RBSXHDIPCIWOMG-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-3-(2-ethylsulfonylimidazo[1,2-a]pyridin-3-yl)sulfonylurea Chemical compound CCS(=O)(=O)C=1N=C2C=CC=CN2C=1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 RBSXHDIPCIWOMG-UHFFFAOYSA-N 0.000 claims 1
- KNGWEAQJZJKFLI-UHFFFAOYSA-N 2,2-dimethyl-4h-1,3-benzodioxine-6-carbaldehyde Chemical compound O=CC1=CC=C2OC(C)(C)OCC2=C1 KNGWEAQJZJKFLI-UHFFFAOYSA-N 0.000 claims 1
- BDQWWOHKFDSADC-UHFFFAOYSA-N 2-(2,4-dichloro-3-methylphenoxy)-n-phenylpropanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C)OC1=CC=C(Cl)C(C)=C1Cl BDQWWOHKFDSADC-UHFFFAOYSA-N 0.000 claims 1
- WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 claims 1
- GOCUAJYOYBLQRH-UHFFFAOYSA-N 2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl GOCUAJYOYBLQRH-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- 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 claims 1
- CABMTIJINOIHOD-UHFFFAOYSA-N 2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]quinoline-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC2=CC=CC=C2C=C1C(O)=O CABMTIJINOIHOD-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- SGVDYFNFBJGOHB-UHFFFAOYSA-N 2-[methyl(phosphonomethyl)amino]acetic acid Chemical compound OC(=O)CN(C)CP(O)(O)=O SGVDYFNFBJGOHB-UHFFFAOYSA-N 0.000 claims 1
- SVOAUHHKPGKPQK-UHFFFAOYSA-N 2-chloro-9-hydroxyfluorene-9-carboxylic acid Chemical compound C1=C(Cl)C=C2C(C(=O)O)(O)C3=CC=CC=C3C2=C1 SVOAUHHKPGKPQK-UHFFFAOYSA-N 0.000 claims 1
- IRCMYGHHKLLGHV-UHFFFAOYSA-N 2-ethoxy-3,3-dimethyl-2,3-dihydro-1-benzofuran-5-yl methanesulfonate Chemical compound C1=C(OS(C)(=O)=O)C=C2C(C)(C)C(OCC)OC2=C1 IRCMYGHHKLLGHV-UHFFFAOYSA-N 0.000 claims 1
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 claims 1
- RRCWSLBKLVBFQD-UHFFFAOYSA-N 4-chloro-1-(2-methylpropyl)imidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C3N(CC(C)C)C=NC3=C(Cl)N=C21 RRCWSLBKLVBFQD-UHFFFAOYSA-N 0.000 claims 1
- CTSLUCNDVMMDHG-UHFFFAOYSA-N 5-bromo-3-(butan-2-yl)-6-methylpyrimidine-2,4(1H,3H)-dione Chemical compound CCC(C)N1C(=O)NC(C)=C(Br)C1=O CTSLUCNDVMMDHG-UHFFFAOYSA-N 0.000 claims 1
- BIHPYCDDPGNWQO-UHFFFAOYSA-N 5-iai Chemical compound C1=C(I)C=C2CC(N)CC2=C1 BIHPYCDDPGNWQO-UHFFFAOYSA-N 0.000 claims 1
- DVOODWOZJVJKQR-UHFFFAOYSA-N 5-tert-butyl-3-(2,4-dichloro-5-prop-2-ynoxyphenyl)-1,3,4-oxadiazol-2-one Chemical group O=C1OC(C(C)(C)C)=NN1C1=CC(OCC#C)=C(Cl)C=C1Cl DVOODWOZJVJKQR-UHFFFAOYSA-N 0.000 claims 1
- 239000002890 Aclonifen Substances 0.000 claims 1
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 claims 1
- 239000003666 Amidosulfuron Substances 0.000 claims 1
- CTTHWASMBLQOFR-UHFFFAOYSA-N Amidosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)N(C)S(C)(=O)=O)=N1 CTTHWASMBLQOFR-UHFFFAOYSA-N 0.000 claims 1
- QGQSRQPXXMTJCM-UHFFFAOYSA-N Benfuresate Chemical compound CCS(=O)(=O)OC1=CC=C2OCC(C)(C)C2=C1 QGQSRQPXXMTJCM-UHFFFAOYSA-N 0.000 claims 1
- 239000005476 Bentazone Substances 0.000 claims 1
- 239000005489 Bromoxynil Substances 0.000 claims 1
- ZOGDSYNXUXQGHF-XIEYBQDHSA-N Butroxydim Chemical compound CCCC(=O)C1=C(C)C=C(C)C(C2CC(=O)C(\C(CC)=N\OCC)=C(O)C2)=C1C ZOGDSYNXUXQGHF-XIEYBQDHSA-N 0.000 claims 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 1
- 239000005490 Carbetamide Substances 0.000 claims 1
- 239000005492 Carfentrazone-ethyl Substances 0.000 claims 1
- 239000005647 Chlorpropham Substances 0.000 claims 1
- WMLPCIHUFDKWJU-UHFFFAOYSA-N Cinosulfuron Chemical compound COCCOC1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC)=NC(OC)=N1 WMLPCIHUFDKWJU-UHFFFAOYSA-N 0.000 claims 1
- 239000005497 Clethodim Substances 0.000 claims 1
- 239000005499 Clomazone Substances 0.000 claims 1
- 239000005500 Clopyralid Substances 0.000 claims 1
- DFCAFRGABIXSDS-UHFFFAOYSA-N Cycloate Chemical compound CCSC(=O)N(CC)C1CCCCC1 DFCAFRGABIXSDS-UHFFFAOYSA-N 0.000 claims 1
- 239000005501 Cycloxydim Substances 0.000 claims 1
- 239000005502 Cyhalofop-butyl Substances 0.000 claims 1
- TYIYMOAHACZAMQ-CQSZACIVSA-N Cyhalofop-butyl Chemical group C1=CC(O[C@H](C)C(=O)OCCCC)=CC=C1OC1=CC=C(C#N)C=C1F TYIYMOAHACZAMQ-CQSZACIVSA-N 0.000 claims 1
- NDUPDOJHUQKPAG-UHFFFAOYSA-N Dalapon Chemical compound CC(Cl)(Cl)C(O)=O NDUPDOJHUQKPAG-UHFFFAOYSA-N 0.000 claims 1
- 239000005644 Dazomet Substances 0.000 claims 1
- QNXAVFXEJCPCJO-UHFFFAOYSA-N Diclosulam Chemical compound N=1N2C(OCC)=NC(F)=CC2=NC=1S(=O)(=O)NC1=C(Cl)C=CC=C1Cl QNXAVFXEJCPCJO-UHFFFAOYSA-N 0.000 claims 1
- 239000005507 Diflufenican Substances 0.000 claims 1
- 239000005508 Dimethachlor Substances 0.000 claims 1
- PHVNLLCAQHGNKU-UHFFFAOYSA-N Dimethipin Chemical compound CC1=C(C)S(=O)(=O)CCS1(=O)=O PHVNLLCAQHGNKU-UHFFFAOYSA-N 0.000 claims 1
- IIPZYDQGBIWLBU-UHFFFAOYSA-N Dinoterb Chemical compound CC(C)(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O IIPZYDQGBIWLBU-UHFFFAOYSA-N 0.000 claims 1
- QAHFOPIILNICLA-UHFFFAOYSA-N Diphenamid Chemical compound C=1C=CC=CC=1C(C(=O)N(C)C)C1=CC=CC=C1 QAHFOPIILNICLA-UHFFFAOYSA-N 0.000 claims 1
- NPWMZOGDXOFZIN-UHFFFAOYSA-N Dipropetryn Chemical compound CCSC1=NC(NC(C)C)=NC(NC(C)C)=N1 NPWMZOGDXOFZIN-UHFFFAOYSA-N 0.000 claims 1
- YUBJPYNSGLJZPQ-UHFFFAOYSA-N Dithiopyr Chemical compound CSC(=O)C1=C(C(F)F)N=C(C(F)(F)F)C(C(=O)SC)=C1CC(C)C YUBJPYNSGLJZPQ-UHFFFAOYSA-N 0.000 claims 1
- BXEHUCNTIZGSOJ-UHFFFAOYSA-N Esprocarb Chemical compound CC(C)C(C)N(CC)C(=O)SCC1=CC=CC=C1 BXEHUCNTIZGSOJ-UHFFFAOYSA-N 0.000 claims 1
- 239000005512 Ethofumesate Substances 0.000 claims 1
- UWVKRNOCDUPIDM-UHFFFAOYSA-N Ethoxysulfuron Chemical compound CCOC1=CC=CC=C1OS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 UWVKRNOCDUPIDM-UHFFFAOYSA-N 0.000 claims 1
- LLQPHQFNMLZJMP-UHFFFAOYSA-N Fentrazamide Chemical compound N1=NN(C=2C(=CC=CC=2)Cl)C(=O)N1C(=O)N(CC)C1CCCCC1 LLQPHQFNMLZJMP-UHFFFAOYSA-N 0.000 claims 1
- 239000005529 Florasulam Substances 0.000 claims 1
- QZXATCCPQKOEIH-UHFFFAOYSA-N Florasulam Chemical compound N=1N2C(OC)=NC=C(F)C2=NC=1S(=O)(=O)NC1=C(F)C=CC=C1F QZXATCCPQKOEIH-UHFFFAOYSA-N 0.000 claims 1
- FICWGWVVIRLNRB-UHFFFAOYSA-N Flucetosulfuron Chemical compound COCC(=O)OC(C(C)F)C1=NC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 FICWGWVVIRLNRB-UHFFFAOYSA-N 0.000 claims 1
- 239000005531 Flufenacet Substances 0.000 claims 1
- IRECWLYBCAZIJM-UHFFFAOYSA-N Flumiclorac pentyl Chemical group C1=C(Cl)C(OCC(=O)OCCCCC)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1F IRECWLYBCAZIJM-UHFFFAOYSA-N 0.000 claims 1
- AOQMRUTZEYVDIL-UHFFFAOYSA-N Flupoxam Chemical compound C=1C=C(Cl)C(COCC(F)(F)C(F)(F)F)=CC=1N1N=C(C(=O)N)N=C1C1=CC=CC=C1 AOQMRUTZEYVDIL-UHFFFAOYSA-N 0.000 claims 1
- PXRROZVNOOEPPZ-UHFFFAOYSA-N Flupropanate Chemical compound OC(=O)C(F)(F)C(F)F PXRROZVNOOEPPZ-UHFFFAOYSA-N 0.000 claims 1
- YWBVHLJPRPCRSD-UHFFFAOYSA-N Fluridone Chemical compound O=C1C(C=2C=C(C=CC=2)C(F)(F)F)=CN(C)C=C1C1=CC=CC=C1 YWBVHLJPRPCRSD-UHFFFAOYSA-N 0.000 claims 1
- 239000005560 Foramsulfuron Substances 0.000 claims 1
- FMGZEUWROYGLAY-UHFFFAOYSA-N Halosulfuron-methyl Chemical group ClC1=NN(C)C(S(=O)(=O)NC(=O)NC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OC FMGZEUWROYGLAY-UHFFFAOYSA-N 0.000 claims 1
- CAWXEEYDBZRFPE-UHFFFAOYSA-N Hexazinone Chemical compound O=C1N(C)C(N(C)C)=NC(=O)N1C1CCCCC1 CAWXEEYDBZRFPE-UHFFFAOYSA-N 0.000 claims 1
- 239000005981 Imazaquin Substances 0.000 claims 1
- 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 claims 1
- PMAAYIYCDXGUAP-UHFFFAOYSA-N Indanofan Chemical compound O=C1C2=CC=CC=C2C(=O)C1(CC)CC1(C=2C=C(Cl)C=CC=2)CO1 PMAAYIYCDXGUAP-UHFFFAOYSA-N 0.000 claims 1
- 239000005571 Isoxaflutole Substances 0.000 claims 1
- UQVYUTAMNICZNI-UHFFFAOYSA-N Karbutilate Chemical compound CN(C)C(=O)NC1=CC=CC(NC(=O)OC(C)(C)C)=C1 UQVYUTAMNICZNI-UHFFFAOYSA-N 0.000 claims 1
- 239000005572 Lenacil Substances 0.000 claims 1
- 239000005573 Linuron Substances 0.000 claims 1
- OKIBNKKYNPBDRS-UHFFFAOYSA-N Mefluidide Chemical compound CC(=O)NC1=CC(NS(=O)(=O)C(F)(F)F)=C(C)C=C1C OKIBNKKYNPBDRS-UHFFFAOYSA-N 0.000 claims 1
- 239000005578 Mesotrione Substances 0.000 claims 1
- 239000005579 Metamitron Substances 0.000 claims 1
- 239000005580 Metazachlor Substances 0.000 claims 1
- RRVIAQKBTUQODI-UHFFFAOYSA-N Methabenzthiazuron Chemical compound C1=CC=C2SC(N(C)C(=O)NC)=NC2=C1 RRVIAQKBTUQODI-UHFFFAOYSA-N 0.000 claims 1
- LRUUNMYPIBZBQH-UHFFFAOYSA-N Methazole Chemical compound O=C1N(C)C(=O)ON1C1=CC=C(Cl)C(Cl)=C1 LRUUNMYPIBZBQH-UHFFFAOYSA-N 0.000 claims 1
- FMINYZXVCTYSNY-UHFFFAOYSA-N Methyldymron Chemical compound C=1C=CC=CC=1N(C)C(=O)NC(C)(C)C1=CC=CC=C1 FMINYZXVCTYSNY-UHFFFAOYSA-N 0.000 claims 1
- 239000005582 Metosulam Substances 0.000 claims 1
- VGHPMIFEKOFHHQ-UHFFFAOYSA-N Metosulam Chemical compound N1=C2N=C(OC)C=C(OC)N2N=C1S(=O)(=O)NC1=C(Cl)C=CC(C)=C1Cl VGHPMIFEKOFHHQ-UHFFFAOYSA-N 0.000 claims 1
- 239000005583 Metribuzin Substances 0.000 claims 1
- WXZVAROIGSFCFJ-UHFFFAOYSA-N N,N-diethyl-2-(naphthalen-1-yloxy)propanamide Chemical compound C1=CC=C2C(OC(C)C(=O)N(CC)CC)=CC=CC2=C1 WXZVAROIGSFCFJ-UHFFFAOYSA-N 0.000 claims 1
- LVKTWOXHRYGDMM-UHFFFAOYSA-N Naproanilide Chemical compound C=1C=C2C=CC=CC2=CC=1OC(C)C(=O)NC1=CC=CC=C1 LVKTWOXHRYGDMM-UHFFFAOYSA-N 0.000 claims 1
- 239000005585 Napropamide Substances 0.000 claims 1
- CCGPUGMWYLICGL-UHFFFAOYSA-N Neburon Chemical compound CCCCN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 CCGPUGMWYLICGL-UHFFFAOYSA-N 0.000 claims 1
- 239000005586 Nicosulfuron Substances 0.000 claims 1
- FJNWCVWQSGGMML-UHFFFAOYSA-N O=C1NC=CC(N1)=O.CF Chemical compound O=C1NC=CC(N1)=O.CF FJNWCVWQSGGMML-UHFFFAOYSA-N 0.000 claims 1
- 239000005589 Oxasulfuron Substances 0.000 claims 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
- 239000005590 Oxyfluorfen Substances 0.000 claims 1
- OQMBBFQZGJFLBU-UHFFFAOYSA-N Oxyfluorfen Chemical compound C1=C([N+]([O-])=O)C(OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 OQMBBFQZGJFLBU-UHFFFAOYSA-N 0.000 claims 1
- SGEJQUSYQTVSIU-UHFFFAOYSA-N Pebulate Chemical compound CCCCN(CC)C(=O)SCCC SGEJQUSYQTVSIU-UHFFFAOYSA-N 0.000 claims 1
- 239000005591 Pendimethalin Substances 0.000 claims 1
- WGVWLKXZBUVUAM-UHFFFAOYSA-N Pentanochlor Chemical compound CCCC(C)C(=O)NC1=CC=C(C)C(Cl)=C1 WGVWLKXZBUVUAM-UHFFFAOYSA-N 0.000 claims 1
- 239000005594 Phenmedipham Substances 0.000 claims 1
- 239000005597 Pinoxaden Substances 0.000 claims 1
- UNLYSVIDNRIVFJ-UHFFFAOYSA-N Piperophos Chemical compound CCCOP(=S)(OCCC)SCC(=O)N1CCCCC1C UNLYSVIDNRIVFJ-UHFFFAOYSA-N 0.000 claims 1
- YLPGTOIOYRQOHV-UHFFFAOYSA-N Pretilachlor Chemical compound CCCOCCN(C(=O)CCl)C1=C(CC)C=CC=C1CC YLPGTOIOYRQOHV-UHFFFAOYSA-N 0.000 claims 1
- 239000005600 Propaquizafop Substances 0.000 claims 1
- 239000005603 Prosulfocarb Substances 0.000 claims 1
- 239000005604 Prosulfuron Substances 0.000 claims 1
- LTUNNEGNEKBSEH-UHFFFAOYSA-N Prosulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)CCC(F)(F)F)=N1 LTUNNEGNEKBSEH-UHFFFAOYSA-N 0.000 claims 1
- VXMNDQDDWDDKOQ-UHFFFAOYSA-N Pyrazosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N(N=CC=2C(O)=O)C)=N1 VXMNDQDDWDDKOQ-UHFFFAOYSA-N 0.000 claims 1
- BGNQYGRXEXDAIQ-UHFFFAOYSA-N Pyrazosulfuron-ethyl Chemical group C1=NN(C)C(S(=O)(=O)NC(=O)NC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OCC BGNQYGRXEXDAIQ-UHFFFAOYSA-N 0.000 claims 1
- 239000005606 Pyridate Substances 0.000 claims 1
- JTZCTMAVMHRNTR-UHFFFAOYSA-N Pyridate Chemical compound CCCCCCCCSC(=O)OC1=CC(Cl)=NN=C1C1=CC=CC=C1 JTZCTMAVMHRNTR-UHFFFAOYSA-N 0.000 claims 1
- 239000005607 Pyroxsulam Substances 0.000 claims 1
- 239000005608 Quinmerac Substances 0.000 claims 1
- OBLNWSCLAYSJJR-UHFFFAOYSA-N Quinoclamin Chemical compound C1=CC=C2C(=O)C(N)=C(Cl)C(=O)C2=C1 OBLNWSCLAYSJJR-UHFFFAOYSA-N 0.000 claims 1
- 239000002167 Quinoclamine Substances 0.000 claims 1
- 239000005616 Rimsulfuron Substances 0.000 claims 1
- CSPPKDPQLUUTND-NBVRZTHBSA-N Sethoxydim Chemical compound CCO\N=C(/CCC)C1=C(O)CC(CC(C)SCC)CC1=O CSPPKDPQLUUTND-NBVRZTHBSA-N 0.000 claims 1
- JXVIIQLNUPXOII-UHFFFAOYSA-N Siduron Chemical compound CC1CCCCC1NC(=O)NC1=CC=CC=C1 JXVIIQLNUPXOII-UHFFFAOYSA-N 0.000 claims 1
- 239000005619 Sulfosulfuron Substances 0.000 claims 1
- HBPDKDSFLXWOAE-UHFFFAOYSA-N Tebuthiuron Chemical compound CNC(=O)N(C)C1=NN=C(C(C)(C)C)S1 HBPDKDSFLXWOAE-UHFFFAOYSA-N 0.000 claims 1
- NBQCNZYJJMBDKY-UHFFFAOYSA-N Terbacil Chemical compound CC=1NC(=O)N(C(C)(C)C)C(=O)C=1Cl NBQCNZYJJMBDKY-UHFFFAOYSA-N 0.000 claims 1
- KDWQYMVPYJGPHS-UHFFFAOYSA-N Thenylchlor Chemical compound C1=CSC(CN(C(=O)CCl)C=2C(=CC=CC=2C)C)=C1OC KDWQYMVPYJGPHS-UHFFFAOYSA-N 0.000 claims 1
- YIJZJEYQBAAWRJ-UHFFFAOYSA-N Thiazopyr Chemical compound N1=C(C(F)F)C(C(=O)OC)=C(CC(C)C)C(C=2SCCN=2)=C1C(F)(F)F YIJZJEYQBAAWRJ-UHFFFAOYSA-N 0.000 claims 1
- 239000005623 Thifensulfuron-methyl Substances 0.000 claims 1
- QHTQREMOGMZHJV-UHFFFAOYSA-N Thiobencarb Chemical compound CCN(CC)C(=O)SCC1=CC=C(Cl)C=C1 QHTQREMOGMZHJV-UHFFFAOYSA-N 0.000 claims 1
- 239000005624 Tralkoxydim Substances 0.000 claims 1
- 239000005627 Triclopyr Substances 0.000 claims 1
- HFBWPRKWDIRYNX-UHFFFAOYSA-N Trietazine Chemical compound CCNC1=NC(Cl)=NC(N(CC)CC)=N1 HFBWPRKWDIRYNX-UHFFFAOYSA-N 0.000 claims 1
- 241000209140 Triticum Species 0.000 claims 1
- 239000005629 Tritosulfuron Substances 0.000 claims 1
- AMRQXHFXNZFDCH-SECBINFHSA-N [(2r)-1-(ethylamino)-1-oxopropan-2-yl] n-phenylcarbamate Chemical compound CCNC(=O)[C@@H](C)OC(=O)NC1=CC=CC=C1 AMRQXHFXNZFDCH-SECBINFHSA-N 0.000 claims 1
- GMAMSSZSJYRYTH-UHFFFAOYSA-N [F].N1=NN=CC=C1 Chemical compound [F].N1=NN=CC=C1 GMAMSSZSJYRYTH-UHFFFAOYSA-N 0.000 claims 1
- HYJODZUSLXOFNC-UHFFFAOYSA-N [S].[Cl] Chemical compound [S].[Cl] HYJODZUSLXOFNC-UHFFFAOYSA-N 0.000 claims 1
- GOIGHUHRYZUEOM-UHFFFAOYSA-N [S].[I] Chemical compound [S].[I] GOIGHUHRYZUEOM-UHFFFAOYSA-N 0.000 claims 1
- NUFNQYOELLVIPL-UHFFFAOYSA-N acifluorfen Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 NUFNQYOELLVIPL-UHFFFAOYSA-N 0.000 claims 1
- DDBMQDADIHOWIC-UHFFFAOYSA-N aclonifen Chemical compound C1=C([N+]([O-])=O)C(N)=C(Cl)C(OC=2C=CC=CC=2)=C1 DDBMQDADIHOWIC-UHFFFAOYSA-N 0.000 claims 1
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 claims 1
- ORFPWVRKFLOQHK-UHFFFAOYSA-N amicarbazone Chemical compound CC(C)C1=NN(C(=O)NC(C)(C)C)C(=O)N1N ORFPWVRKFLOQHK-UHFFFAOYSA-N 0.000 claims 1
- VGPYEHKOIGNJKV-UHFFFAOYSA-N asulam Chemical compound COC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 VGPYEHKOIGNJKV-UHFFFAOYSA-N 0.000 claims 1
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 claims 1
- XOEMATDHVZOBSG-UHFFFAOYSA-N azafenidin Chemical compound C1=C(OCC#C)C(Cl)=CC(Cl)=C1N1C(=O)N2CCCCC2=N1 XOEMATDHVZOBSG-UHFFFAOYSA-N 0.000 claims 1
- ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 claims 1
- CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzidamine Natural products C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 claims 1
- 229910021538 borax Inorganic materials 0.000 claims 1
- WZDDLAZXUYIVMU-UHFFFAOYSA-N bromobutide Chemical compound CC(C)(C)C(Br)C(=O)NC(C)(C)C1=CC=CC=C1 WZDDLAZXUYIVMU-UHFFFAOYSA-N 0.000 claims 1
- HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 claims 1
- VAIZTNZGPYBOGF-UHFFFAOYSA-N butyl 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate Chemical compound C1=CC(OC(C)C(=O)OCCCC)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 VAIZTNZGPYBOGF-UHFFFAOYSA-N 0.000 claims 1
- RSKPLCGMBWEANE-UHFFFAOYSA-N cacodyl Chemical group C[As](C)[As](C)C RSKPLCGMBWEANE-UHFFFAOYSA-N 0.000 claims 1
- HFEJHAAIJZXXRE-UHFFFAOYSA-N cafenstrole Chemical compound CCN(CC)C(=O)N1C=NC(S(=O)(=O)C=2C(=CC(C)=CC=2C)C)=N1 HFEJHAAIJZXXRE-UHFFFAOYSA-N 0.000 claims 1
- NLKUPINTOLSSLD-UHFFFAOYSA-L calcium;4-(1-oxidopropylidene)-3,5-dioxocyclohexane-1-carboxylate Chemical compound [Ca+2].CCC([O-])=C1C(=O)CC(C([O-])=O)CC1=O NLKUPINTOLSSLD-UHFFFAOYSA-L 0.000 claims 1
- GGWHBJGBERXSLL-NBVRZTHBSA-N chembl113137 Chemical compound C1C(=O)C(C(=N/OCC)/CCC)=C(O)CC1C1CSCCC1 GGWHBJGBERXSLL-NBVRZTHBSA-N 0.000 claims 1
- WYKYKTKDBLFHCY-UHFFFAOYSA-N chloridazon Chemical compound O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1 WYKYKTKDBLFHCY-UHFFFAOYSA-N 0.000 claims 1
- NSWAMPCUPHPTTC-UHFFFAOYSA-N chlorimuron-ethyl Chemical group CCOC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(Cl)=CC(OC)=N1 NSWAMPCUPHPTTC-UHFFFAOYSA-N 0.000 claims 1
- JXCGFZXSOMJFOA-UHFFFAOYSA-N chlorotoluron Chemical compound CN(C)C(=O)NC1=CC=C(C)C(Cl)=C1 JXCGFZXSOMJFOA-UHFFFAOYSA-N 0.000 claims 1
- CWJSHJJYOPWUGX-UHFFFAOYSA-N chlorpropham Chemical compound CC(C)OC(=O)NC1=CC=CC(Cl)=C1 CWJSHJJYOPWUGX-UHFFFAOYSA-N 0.000 claims 1
- NNKKTZOEKDFTBU-YBEGLDIGSA-N cinidon ethyl Chemical compound C1=C(Cl)C(/C=C(\Cl)C(=O)OCC)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1 NNKKTZOEKDFTBU-YBEGLDIGSA-N 0.000 claims 1
- SILSDTWXNBZOGF-JWGBMQLESA-N clethodim Chemical compound CCSC(C)CC1CC(O)=C(C(CC)=NOC\C=C\Cl)C(=O)C1 SILSDTWXNBZOGF-JWGBMQLESA-N 0.000 claims 1
- KIEDNEWSYUYDSN-UHFFFAOYSA-N clomazone Chemical compound O=C1C(C)(C)CON1CC1=CC=CC=C1Cl KIEDNEWSYUYDSN-UHFFFAOYSA-N 0.000 claims 1
- HUBANNPOLNYSAD-UHFFFAOYSA-N clopyralid Chemical compound OC(=O)C1=NC(Cl)=CC=C1Cl HUBANNPOLNYSAD-UHFFFAOYSA-N 0.000 claims 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- QAYICIQNSGETAS-UHFFFAOYSA-N dazomet Chemical compound CN1CSC(=S)N(C)C1 QAYICIQNSGETAS-UHFFFAOYSA-N 0.000 claims 1
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- BWUPSGJXXPATLU-UHFFFAOYSA-N dimepiperate Chemical compound C=1C=CC=CC=1C(C)(C)SC(=O)N1CCCCC1 BWUPSGJXXPATLU-UHFFFAOYSA-N 0.000 claims 1
- SCCDDNKJYDZXMM-UHFFFAOYSA-N dimethachlor Chemical compound COCCN(C(=O)CCl)C1=C(C)C=CC=C1C SCCDDNKJYDZXMM-UHFFFAOYSA-N 0.000 claims 1
- IRLGCAJYYKDTCG-UHFFFAOYSA-N ethametsulfuron Chemical compound CCOC1=NC(NC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 IRLGCAJYYKDTCG-UHFFFAOYSA-N 0.000 claims 1
- ZINJLDJMHCUBIP-UHFFFAOYSA-N ethametsulfuron-methyl Chemical group CCOC1=NC(NC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(=O)OC)=N1 ZINJLDJMHCUBIP-UHFFFAOYSA-N 0.000 claims 1
- MLKCGVHIFJBRCD-UHFFFAOYSA-N ethyl 2-chloro-3-{2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-4-fluorophenyl}propanoate Chemical group C1=C(Cl)C(CC(Cl)C(=O)OCC)=CC(N2C(N(C(F)F)C(C)=N2)=O)=C1F MLKCGVHIFJBRCD-UHFFFAOYSA-N 0.000 claims 1
- VAIZTNZGPYBOGF-CYBMUJFWSA-N fluazifop-P-butyl Chemical group C1=CC(O[C@H](C)C(=O)OCCCC)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 VAIZTNZGPYBOGF-CYBMUJFWSA-N 0.000 claims 1
- UOUXAYAIONPXDH-UHFFFAOYSA-M flucarbazone-sodium Chemical compound [Na+].O=C1N(C)C(OC)=NN1C(=O)[N-]S(=O)(=O)C1=CC=CC=C1OC(F)(F)F UOUXAYAIONPXDH-UHFFFAOYSA-M 0.000 claims 1
- IANUJLZYFUDJIH-UHFFFAOYSA-N flufenacet Chemical compound C=1C=C(F)C=CC=1N(C(C)C)C(=O)COC1=NN=C(C(F)(F)F)S1 IANUJLZYFUDJIH-UHFFFAOYSA-N 0.000 claims 1
- DNUAYCRATWAJQE-UHFFFAOYSA-N flufenpyr-ethyl Chemical group C1=C(Cl)C(OCC(=O)OCC)=CC(N2C(C(C)=C(C=N2)C(F)(F)F)=O)=C1F DNUAYCRATWAJQE-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- OQZCSNDVOWYALR-UHFFFAOYSA-N flurochloridone Chemical compound FC(F)(F)C1=CC=CC(N2C(C(Cl)C(CCl)C2)=O)=C1 OQZCSNDVOWYALR-UHFFFAOYSA-N 0.000 claims 1
- XWROTTLWMHCFEC-LGMDPLHJSA-N fluthiacet Chemical compound C1=C(Cl)C(SCC(=O)O)=CC(\N=C/2N3CCCCN3C(=O)S\2)=C1F XWROTTLWMHCFEC-LGMDPLHJSA-N 0.000 claims 1
- ZCNQYNHDVRPZIH-UHFFFAOYSA-N fluthiacet-methyl Chemical compound C1=C(Cl)C(SCC(=O)OC)=CC(N=C2N3CCCCN3C(=O)S2)=C1F ZCNQYNHDVRPZIH-UHFFFAOYSA-N 0.000 claims 1
- BGZZWXTVIYUUEY-UHFFFAOYSA-N fomesafen Chemical compound C1=C([N+]([O-])=O)C(C(=O)NS(=O)(=O)C)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 BGZZWXTVIYUUEY-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- 244000230342 green foxtail Species 0.000 claims 1
- MFSWTRQUCLNFOM-SECBINFHSA-N haloxyfop-P-methyl Chemical group C1=CC(O[C@H](C)C(=O)OC)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl MFSWTRQUCLNFOM-SECBINFHSA-N 0.000 claims 1
- YFONKFDEZLYQDH-BOURZNODSA-N indaziflam Chemical compound CC(F)C1=NC(N)=NC(N[C@H]2C3=CC(C)=CC=C3C[C@@H]2C)=N1 YFONKFDEZLYQDH-BOURZNODSA-N 0.000 claims 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims 1
- PUIYMUZLKQOUOZ-UHFFFAOYSA-N isoproturon Chemical compound CC(C)C1=CC=C(NC(=O)N(C)C)C=C1 PUIYMUZLKQOUOZ-UHFFFAOYSA-N 0.000 claims 1
- OYIKARCXOQLFHF-UHFFFAOYSA-N isoxaflutole Chemical compound CS(=O)(=O)C1=CC(C(F)(F)F)=CC=C1C(=O)C1=C(C2CC2)ON=C1 OYIKARCXOQLFHF-UHFFFAOYSA-N 0.000 claims 1
- 229940088649 isoxaflutole Drugs 0.000 claims 1
- ZTMKADLOSYKWCA-UHFFFAOYSA-N lenacil Chemical compound O=C1NC=2CCCC=2C(=O)N1C1CCCCC1 ZTMKADLOSYKWCA-UHFFFAOYSA-N 0.000 claims 1
- XIGAUIHYSDTJHW-UHFFFAOYSA-N mefenacet Chemical compound N=1C2=CC=CC=C2SC=1OCC(=O)N(C)C1=CC=CC=C1 XIGAUIHYSDTJHW-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- VHCNQEUWZYOAEV-UHFFFAOYSA-N metamitron Chemical compound O=C1N(N)C(C)=NN=C1C1=CC=CC=C1 VHCNQEUWZYOAEV-UHFFFAOYSA-N 0.000 claims 1
- STEPQTYSZVCJPV-UHFFFAOYSA-N metazachlor Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)CN1N=CC=C1 STEPQTYSZVCJPV-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- JTHMVYBOQLDDIY-UHFFFAOYSA-N methyl 2-[(4-methyl-5-oxo-3-propoxy-1,2,4-triazole-1-carbonyl)sulfamoyl]benzoate Chemical compound O=C1N(C)C(OCCC)=NN1C(=O)NS(=O)(=O)C1=CC=CC=C1C(=O)OC JTHMVYBOQLDDIY-UHFFFAOYSA-N 0.000 claims 1
- LYPWWQLKWQNQKV-UHFFFAOYSA-N methyl 2-[5-ethyl-2-[[4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]methyl]phenoxy]propanoate Chemical compound COC(=O)C(C)OC1=CC(CC)=CC=C1COC1=CC=C(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)C=C1 LYPWWQLKWQNQKV-UHFFFAOYSA-N 0.000 claims 1
- ZTYVMAQSHCZXLF-UHFFFAOYSA-N methyl 2-[[4,6-bis(difluoromethoxy)pyrimidin-2-yl]carbamoylsulfamoyl]benzoate Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC(F)F)=CC(OC(F)F)=N1 ZTYVMAQSHCZXLF-UHFFFAOYSA-N 0.000 claims 1
- LINPVWIEWJTEEJ-UHFFFAOYSA-N methyl 2-chloro-9-hydroxyfluorene-9-carboxylate Chemical group C1=C(Cl)C=C2C(C(=O)OC)(O)C3=CC=CC=C3C2=C1 LINPVWIEWJTEEJ-UHFFFAOYSA-N 0.000 claims 1
- NDNKHWUXXOFHTD-UHFFFAOYSA-N metizoline Chemical compound CC=1SC2=CC=CC=C2C=1CC1=NCCN1 NDNKHWUXXOFHTD-UHFFFAOYSA-N 0.000 claims 1
- DSRNRYQBBJQVCW-UHFFFAOYSA-N metoxuron Chemical compound COC1=CC=C(NC(=O)N(C)C)C=C1Cl DSRNRYQBBJQVCW-UHFFFAOYSA-N 0.000 claims 1
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 claims 1
- RSMUVYRMZCOLBH-UHFFFAOYSA-N metsulfuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 RSMUVYRMZCOLBH-UHFFFAOYSA-N 0.000 claims 1
- DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 claims 1
- AIMMSOZBPYFASU-UHFFFAOYSA-N n-(4,6-dimethoxypyrimidin-2-yl)-n'-[3-(2,2,2-trifluoroethoxy)pyridin-1-ium-2-yl]sulfonylcarbamimidate Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)OCC(F)(F)F)=N1 AIMMSOZBPYFASU-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- JXTHEWSKYLZVJC-UHFFFAOYSA-N naptalam Chemical compound OC(=O)C1=CC=CC=C1C(=O)NC1=CC=CC2=CC=CC=C12 JXTHEWSKYLZVJC-UHFFFAOYSA-N 0.000 claims 1
- RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 claims 1
- LLLFASISUZUJEQ-UHFFFAOYSA-N orbencarb Chemical compound CCN(CC)C(=O)SCC1=CC=CC=C1Cl LLLFASISUZUJEQ-UHFFFAOYSA-N 0.000 claims 1
- UCDPMNSCCRBWIC-UHFFFAOYSA-N orthosulfamuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)NC=2C(=CC=CC=2)C(=O)N(C)C)=N1 UCDPMNSCCRBWIC-UHFFFAOYSA-N 0.000 claims 1
- 235000006408 oxalic acid Nutrition 0.000 claims 1
- IOXAXYHXMLCCJJ-UHFFFAOYSA-N oxetan-3-yl 2-[(4,6-dimethylpyrimidin-2-yl)carbamoylsulfamoyl]benzoate Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(=O)OC2COC2)=N1 IOXAXYHXMLCCJJ-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- IDOWTHOLJBTAFI-UHFFFAOYSA-N phenmedipham Chemical compound COC(=O)NC1=CC=CC(OC(=O)NC=2C=C(C)C=CC=2)=C1 IDOWTHOLJBTAFI-UHFFFAOYSA-N 0.000 claims 1
- HOKBIQDJCNTWST-UHFFFAOYSA-N phosphanylidenezinc;zinc Chemical compound [Zn].[Zn]=P.[Zn]=P HOKBIQDJCNTWST-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- ISEUFVQQFVOBCY-UHFFFAOYSA-N prometon Chemical compound COC1=NC(NC(C)C)=NC(NC(C)C)=N1 ISEUFVQQFVOBCY-UHFFFAOYSA-N 0.000 claims 1
- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 claims 1
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 claims 1
- FKLQIONHGSFYJY-UHFFFAOYSA-N propan-2-yl 5-[4-bromo-1-methyl-5-(trifluoromethyl)pyrazol-3-yl]-2-chloro-4-fluorobenzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(C=2C(=C(N(C)N=2)C(F)(F)F)Br)=C1F FKLQIONHGSFYJY-UHFFFAOYSA-N 0.000 claims 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 claims 1
- WJNRPILHGGKWCK-UHFFFAOYSA-N propazine Chemical compound CC(C)NC1=NC(Cl)=NC(NC(C)C)=N1 WJNRPILHGGKWCK-UHFFFAOYSA-N 0.000 claims 1
- VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 claims 1
- PHNUZKMIPFFYSO-UHFFFAOYSA-N propyzamide Chemical compound C#CC(C)(C)NC(=O)C1=CC(Cl)=CC(Cl)=C1 PHNUZKMIPFFYSO-UHFFFAOYSA-N 0.000 claims 1
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 claims 1
- APTZNLHMIGJTEW-UHFFFAOYSA-N pyraflufen-ethyl Chemical group C1=C(Cl)C(OCC(=O)OCC)=CC(C=2C(=C(OC(F)F)N(C)N=2)Cl)=C1F APTZNLHMIGJTEW-UHFFFAOYSA-N 0.000 claims 1
- ASRAWSBMDXVNLX-UHFFFAOYSA-N pyrazolynate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OS(=O)(=O)C1=CC=C(C)C=C1 ASRAWSBMDXVNLX-UHFFFAOYSA-N 0.000 claims 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 claims 1
- USSIUIGPBLPCDF-KEBDBYFISA-N pyriminobac-methyl Chemical compound CO\N=C(/C)C1=CC=CC(OC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OC USSIUIGPBLPCDF-KEBDBYFISA-N 0.000 claims 1
- NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 claims 1
- ALZOLUNSQWINIR-UHFFFAOYSA-N quinmerac Chemical compound OC(=O)C1=C(Cl)C=CC2=CC(C)=CN=C21 ALZOLUNSQWINIR-UHFFFAOYSA-N 0.000 claims 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 claims 1
- MEFOUWRMVYJCQC-UHFFFAOYSA-N rimsulfuron Chemical compound CCS(=O)(=O)C1=CC=CN=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 MEFOUWRMVYJCQC-UHFFFAOYSA-N 0.000 claims 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 claims 1
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 claims 1
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 claims 1
- 239000004328 sodium tetraborate Substances 0.000 claims 1
- 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 claims 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 claims 1
- OORLZFUTLGXMEF-UHFFFAOYSA-N sulfentrazone Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(NS(C)(=O)=O)=C(Cl)C=C1Cl OORLZFUTLGXMEF-UHFFFAOYSA-N 0.000 claims 1
- ZDXMLEQEMNLCQG-UHFFFAOYSA-N sulfometuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 ZDXMLEQEMNLCQG-UHFFFAOYSA-N 0.000 claims 1
- BCQMBFHBDZVHKU-UHFFFAOYSA-N terbumeton Chemical compound CCNC1=NC(NC(C)(C)C)=NC(OC)=N1 BCQMBFHBDZVHKU-UHFFFAOYSA-N 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 229930192474 thiophene Natural products 0.000 claims 1
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 claims 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 claims 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 claims 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 claims 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 claims 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 claims 1
- 230000000694 effects Effects 0.000 abstract description 9
- 238000009333 weeding Methods 0.000 abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
- 239000002585 base Substances 0.000 description 36
- 239000000243 solution Substances 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- 239000002904 solvent Substances 0.000 description 27
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 24
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 22
- 235000019439 ethyl acetate Nutrition 0.000 description 22
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
- 240000008042 Zea mays Species 0.000 description 21
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 21
- 239000007787 solid Substances 0.000 description 21
- 239000003513 alkali Substances 0.000 description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
- 241000192043 Echinochloa Species 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
- 241000209082 Lolium Species 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 235000019441 ethanol Nutrition 0.000 description 16
- 238000005160 1H NMR spectroscopy Methods 0.000 description 15
- 244000075850 Avena orientalis Species 0.000 description 15
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 15
- 241000209117 Panicum Species 0.000 description 15
- 235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 15
- 235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 15
- 239000003153 chemical reaction reagent Substances 0.000 description 15
- 241000611157 Brachiaria Species 0.000 description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 14
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 14
- 235000005822 corn Nutrition 0.000 description 14
- 239000007921 spray Substances 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000004094 surface-active agent Substances 0.000 description 13
- 235000005775 Setaria Nutrition 0.000 description 12
- 241000232088 Setaria <nematode> Species 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- 229910000104 sodium hydride Inorganic materials 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 241000209120 Cenchrus Species 0.000 description 11
- 235000015424 sodium Nutrition 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 241000743339 Agrostis Species 0.000 description 9
- 235000005781 Avena Nutrition 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 241000255964 Pieridae Species 0.000 description 9
- 244000062793 Sorghum vulgare Species 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- 239000000376 reactant Substances 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 240000001592 Amaranthus caudatus Species 0.000 description 8
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 8
- 241000320639 Leptochloa Species 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
- 240000006394 Sorghum bicolor Species 0.000 description 8
- 230000008859 change Effects 0.000 description 8
- 238000003818 flash chromatography Methods 0.000 description 8
- 150000004702 methyl esters Chemical class 0.000 description 8
- 239000004530 micro-emulsion Substances 0.000 description 8
- 239000005416 organic matter Substances 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
- 239000012312 sodium hydride Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 244000098338 Triticum aestivum Species 0.000 description 7
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 7
- 239000004495 emulsifiable concentrate Substances 0.000 description 7
- 239000008187 granular material Substances 0.000 description 7
- 125000000623 heterocyclic group Chemical group 0.000 description 7
- 238000005286 illumination Methods 0.000 description 7
- 235000009973 maize Nutrition 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 235000007319 Avena orientalis Nutrition 0.000 description 6
- 0 B*(C)c1c(*)ncc(C)c1* Chemical compound B*(C)c1c(*)ncc(C)c1* 0.000 description 6
- 235000017896 Digitaria Nutrition 0.000 description 6
- 241001303487 Digitaria <clam> Species 0.000 description 6
- 235000007351 Eleusine Nutrition 0.000 description 6
- 241000209215 Eleusine Species 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- 241000209046 Pennisetum Species 0.000 description 6
- 241000745991 Phalaris Species 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 235000006386 Polygonum aviculare Nutrition 0.000 description 6
- 244000292697 Polygonum aviculare Species 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- 239000000080 wetting agent Substances 0.000 description 6
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical compound NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 description 5
- 241001647031 Avena sterilis Species 0.000 description 5
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 5
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 5
- 241000044408 Eriochloa Species 0.000 description 5
- 240000007594 Oryza sativa Species 0.000 description 5
- 235000007164 Oryza sativa Nutrition 0.000 description 5
- 241000857233 Rottboellia Species 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 5
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 235000019253 formic acid Nutrition 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- 235000009566 rice Nutrition 0.000 description 5
- 241000894007 species Species 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- 241000743985 Alopecurus Species 0.000 description 4
- 241001621841 Alopecurus myosuroides Species 0.000 description 4
- 241001666377 Apera Species 0.000 description 4
- 235000007320 Avena fatua Nutrition 0.000 description 4
- 235000004535 Avena sterilis Nutrition 0.000 description 4
- 241000209200 Bromus Species 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- 241000234653 Cyperus Species 0.000 description 4
- 244000299507 Gossypium hirsutum Species 0.000 description 4
- 241000209510 Liliopsida Species 0.000 description 4
- 240000004296 Lolium perenne Species 0.000 description 4
- 240000000178 Monochoria vaginalis Species 0.000 description 4
- 244000081757 Phalaris arundinacea Species 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 4
- 241000202758 Scirpus Species 0.000 description 4
- 241000820163 Setaria leucopila Species 0.000 description 4
- 235000001155 Setaria leucopila Nutrition 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- OBNCKNCVKJNDBV-UHFFFAOYSA-N ethyl butyrate Chemical group CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 4
- 244000304962 green bristle grass Species 0.000 description 4
- 230000012010 growth Effects 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 239000004546 suspension concentrate Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 4
- 239000004563 wettable powder Substances 0.000 description 4
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 3
- 241000219144 Abutilon Species 0.000 description 3
- 235000007516 Chrysanthemum Nutrition 0.000 description 3
- 241000234646 Cyperaceae Species 0.000 description 3
- GMBRUAIJEFRHFQ-UHFFFAOYSA-N Fenchlorazole-ethyl Chemical group N1=C(C(=O)OCC)N=C(C(Cl)(Cl)Cl)N1C1=CC=C(Cl)C=C1Cl GMBRUAIJEFRHFQ-UHFFFAOYSA-N 0.000 description 3
- 241000238631 Hexapoda Species 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 235000003990 Monochoria hastata Nutrition 0.000 description 3
- 241000069499 Ottochloa Species 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 241000209048 Poa Species 0.000 description 3
- 244000292693 Poa annua Species 0.000 description 3
- 241000209504 Poaceae Species 0.000 description 3
- 235000008515 Setaria glauca Nutrition 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 239000003905 agrochemical Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 239000000010 aprotic solvent Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000009395 breeding Methods 0.000 description 3
- 235000001465 calcium Nutrition 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- COYBRKAVBMYYSF-UHFFFAOYSA-N heptan-2-yl [(5-chloroquinolin-8-yl)oxy]acetate Chemical group C1=CN=C2C(OCC(=O)OC(C)CCCCC)=CC=C(Cl)C2=C1 COYBRKAVBMYYSF-UHFFFAOYSA-N 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 230000002147 killing effect Effects 0.000 description 3
- 244000144886 lesser spear grass Species 0.000 description 3
- 235000019713 millet Nutrition 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000012266 salt solution Substances 0.000 description 3
- 239000003053 toxin Substances 0.000 description 3
- 231100000765 toxin Toxicity 0.000 description 3
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 150000000094 1,4-dioxanes Chemical class 0.000 description 2
- 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 2
- QWWHRELOCZEQNZ-UHFFFAOYSA-N 2,2-dichloro-1-(1-oxa-4-azaspiro[4.5]decan-4-yl)ethanone Chemical compound ClC(Cl)C(=O)N1CCOC11CCCCC1 QWWHRELOCZEQNZ-UHFFFAOYSA-N 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- 125000006012 2-chloroethoxy group Chemical group 0.000 description 2
- ZRNSSRODJSSVEJ-UHFFFAOYSA-N 2-methylpentacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(C)C ZRNSSRODJSSVEJ-UHFFFAOYSA-N 0.000 description 2
- 150000005710 5-bromopyrimidines Chemical class 0.000 description 2
- 241000219318 Amaranthus Species 0.000 description 2
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 2
- 244000237956 Amaranthus retroflexus Species 0.000 description 2
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 2
- 241001148727 Bromus tectorum Species 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 208000003643 Callosities Diseases 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 241000219312 Chenopodium Species 0.000 description 2
- 235000000509 Chenopodium ambrosioides Nutrition 0.000 description 2
- 244000098897 Chenopodium botrys Species 0.000 description 2
- 235000005490 Chenopodium botrys Nutrition 0.000 description 2
- 240000005250 Chrysanthemum indicum Species 0.000 description 2
- 241000132542 Conyza Species 0.000 description 2
- 240000002092 Echinochloa colona Species 0.000 description 2
- 235000014716 Eleusine indica Nutrition 0.000 description 2
- 244000025670 Eleusine indica Species 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 241001553700 Euphorbia lathyris Species 0.000 description 2
- 241001290564 Fimbristylis Species 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 241001101998 Galium Species 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 241000461680 Hymenachne hemitomon Species 0.000 description 2
- 206010020649 Hyperkeratosis Diseases 0.000 description 2
- 235000021506 Ipomoea Nutrition 0.000 description 2
- 241000207783 Ipomoea Species 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 241000110847 Kochia Species 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 235000015225 Panicum colonum Nutrition 0.000 description 2
- 244000038248 Pennisetum spicatum Species 0.000 description 2
- 235000007195 Pennisetum typhoides Nutrition 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 235000014676 Phragmites communis Nutrition 0.000 description 2
- 244000273256 Phragmites communis Species 0.000 description 2
- 241000205407 Polygonum Species 0.000 description 2
- 229920001213 Polysorbate 20 Polymers 0.000 description 2
- 229920001214 Polysorbate 60 Polymers 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 240000009132 Sagittaria sagittifolia Species 0.000 description 2
- 241001355178 Setaria faberi Species 0.000 description 2
- 235000017016 Setaria faberi Nutrition 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 235000002634 Solanum Nutrition 0.000 description 2
- 241000207763 Solanum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 240000002439 Sorghum halepense Species 0.000 description 2
- 240000006694 Stellaria media Species 0.000 description 2
- 240000001260 Tropaeolum majus Species 0.000 description 2
- 235000004424 Tropaeolum majus Nutrition 0.000 description 2
- 241000405217 Viola <butterfly> Species 0.000 description 2
- 241001506766 Xanthium Species 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 210000000481 breast Anatomy 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000004490 capsule suspension Substances 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- WMSPXQIQBQAWLL-UHFFFAOYSA-N cyclopropanesulfonamide Chemical compound NS(=O)(=O)C1CC1 WMSPXQIQBQAWLL-UHFFFAOYSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000012407 engineering method Methods 0.000 description 2
- 230000008029 eradication Effects 0.000 description 2
- 239000000686 essence Substances 0.000 description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000010353 genetic engineering Methods 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- IGMNYECMUMZDDF-UHFFFAOYSA-N homogentisic acid Chemical compound OC(=O)CC1=CC(O)=CC=C1O IGMNYECMUMZDDF-UHFFFAOYSA-N 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- MWKVXOJATACCCH-UHFFFAOYSA-N isoxadifen-ethyl Chemical group C1C(C(=O)OCC)=NOC1(C=1C=CC=CC=1)C1=CC=CC=C1 MWKVXOJATACCCH-UHFFFAOYSA-N 0.000 description 2
- 235000015110 jellies Nutrition 0.000 description 2
- 239000008274 jelly Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 235000001055 magnesium Nutrition 0.000 description 2
- 229940091250 magnesium supplement Drugs 0.000 description 2
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 2
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 2
- NBVXSUQYWXRMNV-UHFFFAOYSA-N monofluoromethane Natural products FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000007764 o/w emulsion Substances 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229960003742 phenol Drugs 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000003880 polar aprotic solvent Substances 0.000 description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 235000007686 potassium Nutrition 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000013049 sediment Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L sodium sulphate Substances [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
- 229960000278 theophylline Drugs 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- JRHPOFJADXHYBR-HTQZYQBOSA-N (1r,2r)-1-n,2-n-dimethylcyclohexane-1,2-diamine Chemical class CN[C@@H]1CCCC[C@H]1NC JRHPOFJADXHYBR-HTQZYQBOSA-N 0.000 description 1
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 1
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 1
- 150000005071 1,2,4-oxadiazoles Chemical class 0.000 description 1
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 1
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 1
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 description 1
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 description 1
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 description 1
- 150000004869 1,3,4-thiadiazoles Chemical class 0.000 description 1
- HMOPMAWBRBERLG-UHFFFAOYSA-N 1-methyl-6-(trifluoromethyl)pyrimidine-2,4-dione Chemical compound CN1C(C(F)(F)F)=CC(=O)NC1=O HMOPMAWBRBERLG-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical class OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 description 1
- AMFYRKOUWBAGHV-UHFFFAOYSA-N 1h-pyrazolo[4,3-b]pyridine Chemical class C1=CN=C2C=NNC2=C1 AMFYRKOUWBAGHV-UHFFFAOYSA-N 0.000 description 1
- QLSWIGRIBOSFMV-UHFFFAOYSA-N 1h-pyrrol-2-amine Chemical compound NC1=CC=CN1 QLSWIGRIBOSFMV-UHFFFAOYSA-N 0.000 description 1
- 125000004797 2,2,2-trichloroethoxy group Chemical group ClC(CO*)(Cl)Cl 0.000 description 1
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- VUCGAFPTLRWSEB-UHFFFAOYSA-N 2-[2-(2-dodecoxyethoxy)ethoxy]acetic acid Chemical compound CCCCCCCCCCCCOCCOCCOCC(O)=O VUCGAFPTLRWSEB-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- GAWAYYRQGQZKCR-UHFFFAOYSA-N 2-chloropropionic acid Chemical class CC(Cl)C(O)=O GAWAYYRQGQZKCR-UHFFFAOYSA-N 0.000 description 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- CBQDTCDOVVBGMN-UHFFFAOYSA-N 2-methyl-3-octylphenol Chemical compound CCCCCCCCC1=CC=CC(O)=C1C CBQDTCDOVVBGMN-UHFFFAOYSA-N 0.000 description 1
- DUIOKRXOKLLURE-UHFFFAOYSA-N 2-octylphenol Chemical compound CCCCCCCCC1=CC=CC=C1O DUIOKRXOKLLURE-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- XYVMOLOUBJBNBF-UHFFFAOYSA-N 3h-1,3-oxazol-2-one Chemical class OC1=NC=CO1 XYVMOLOUBJBNBF-UHFFFAOYSA-N 0.000 description 1
- WHJDTUHLRPOPSK-UHFFFAOYSA-N 4-amino-4-oxo-3-sulfobutanoic acid Chemical class NC(=O)C(S(O)(=O)=O)CC(O)=O WHJDTUHLRPOPSK-UHFFFAOYSA-N 0.000 description 1
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 1
- SFHYNDMGZXWXBU-LIMNOBDPSA-N 6-amino-2-[[(e)-(3-formylphenyl)methylideneamino]carbamoylamino]-1,3-dioxobenzo[de]isoquinoline-5,8-disulfonic acid Chemical compound O=C1C(C2=3)=CC(S(O)(=O)=O)=CC=3C(N)=C(S(O)(=O)=O)C=C2C(=O)N1NC(=O)N\N=C\C1=CC=CC(C=O)=C1 SFHYNDMGZXWXBU-LIMNOBDPSA-N 0.000 description 1
- ZUSHSDOEVHPTCU-UHFFFAOYSA-N 6-chloro-3-phenyl-1h-pyridazin-4-one Chemical compound N1C(Cl)=CC(=O)C(C=2C=CC=CC=2)=N1 ZUSHSDOEVHPTCU-UHFFFAOYSA-N 0.000 description 1
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical class N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 1
- 241001290610 Abildgaardia Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241000254175 Anthonomus grandis Species 0.000 description 1
- 241000209764 Avena fatua Species 0.000 description 1
- 235000011635 Avena sterilis subsp ludoviciana Nutrition 0.000 description 1
- IVRMZWNICZWHMI-UHFFFAOYSA-N Azide Chemical compound [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 1
- 241000193388 Bacillus thuringiensis Species 0.000 description 1
- PFJJMJDEVDLPNE-UHFFFAOYSA-N Benoxacor Chemical compound C1=CC=C2N(C(=O)C(Cl)Cl)C(C)COC2=C1 PFJJMJDEVDLPNE-UHFFFAOYSA-N 0.000 description 1
- RRNIZKPFKNDSRS-UHFFFAOYSA-N Bensulide Chemical compound CC(C)OP(=S)(OC(C)C)SCCNS(=O)(=O)C1=CC=CC=C1 RRNIZKPFKNDSRS-UHFFFAOYSA-N 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 244000148500 Bolboschoenus maritimus Species 0.000 description 1
- 235000014698 Brassica juncea var multisecta Nutrition 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000006008 Brassica napus var napus Nutrition 0.000 description 1
- 235000006618 Brassica rapa subsp oleifera Nutrition 0.000 description 1
- 244000188595 Brassica sinapistrum Species 0.000 description 1
- 241000981770 Buddleja asiatica Species 0.000 description 1
- DZAHXNNEQCZPGJ-UHFFFAOYSA-N CCCCOC(OC)=O.COC(O)=O Chemical class CCCCOC(OC)=O.COC(O)=O DZAHXNNEQCZPGJ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 244000189548 Chrysanthemum x morifolium Species 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 241001573881 Corolla Species 0.000 description 1
- 238000006969 Curtius rearrangement reaction Methods 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 235000005462 Digitaria horizontalis Nutrition 0.000 description 1
- 241000163589 Digitaria horizontalis Species 0.000 description 1
- 235000003664 Digitaria insularis Nutrition 0.000 description 1
- 241000718034 Digitaria insularis Species 0.000 description 1
- 244000152970 Digitaria sanguinalis Species 0.000 description 1
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
- 241000771421 Dinebra panicoides Species 0.000 description 1
- 244000239348 Echinochloa crus galli var. praticola Species 0.000 description 1
- 240000002358 Echinochloa oryzoides Species 0.000 description 1
- 244000078127 Eleusine coracana Species 0.000 description 1
- 235000013499 Eleusine coracana subsp coracana Nutrition 0.000 description 1
- 241001299722 Eriochloa villosa Species 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- NRFQZTCQAYEXEE-UHFFFAOYSA-N Fenclorim Chemical compound ClC1=CC(Cl)=NC(C=2C=CC=CC=2)=N1 NRFQZTCQAYEXEE-UHFFFAOYSA-N 0.000 description 1
- DHAHEVIQIYRFRG-UHFFFAOYSA-N Fluoroglycofen Chemical compound C1=C([N+]([O-])=O)C(C(=O)OCC(=O)O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 DHAHEVIQIYRFRG-UHFFFAOYSA-N 0.000 description 1
- UKSLKNUCVPZQCQ-UHFFFAOYSA-N Fluxofenim Chemical compound C=1C=C(Cl)C=CC=1C(C(F)(F)F)=NOCC1OCCO1 UKSLKNUCVPZQCQ-UHFFFAOYSA-N 0.000 description 1
- 239000005561 Glufosinate Substances 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 238000012696 Interfacial polycondensation Methods 0.000 description 1
- 241000731961 Juncaceae Species 0.000 description 1
- 241000735470 Juncus Species 0.000 description 1
- 241001408874 Juncus acutiflorus Species 0.000 description 1
- 241000254158 Lampyridae Species 0.000 description 1
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 1
- 244000143149 Leptochloa chinensis Species 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 244000100545 Lolium multiflorum Species 0.000 description 1
- 241000033018 Lolium persicum Species 0.000 description 1
- 241000033016 Lolium rigidum Species 0.000 description 1
- 241000237852 Mollusca Species 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- QSMTUAJDOTXEDZ-UHFFFAOYSA-N N1C=CC=C1.[Cl] Chemical class N1C=CC=C1.[Cl] QSMTUAJDOTXEDZ-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- AYDQIZKZTQHYIY-UHFFFAOYSA-N OC(=O)C1(C)CC(C(O)=O)=CC=C1 Chemical compound OC(=O)C1(C)CC(C(O)=O)=CC=C1 AYDQIZKZTQHYIY-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 241001147398 Ostrinia nubilalis Species 0.000 description 1
- WFVUIONFJOAYPK-KAMYIIQDSA-N Oxabetrinil Chemical compound C=1C=CC=CC=1C(/C#N)=N\OCC1OCCO1 WFVUIONFJOAYPK-KAMYIIQDSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 235000006484 Paeonia officinalis Nutrition 0.000 description 1
- 244000170916 Paeonia officinalis Species 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 241001148659 Panicum dichotomiflorum Species 0.000 description 1
- 235000007199 Panicum miliaceum Nutrition 0.000 description 1
- 241000257649 Phalaris minor Species 0.000 description 1
- 241000461749 Phalaris paradoxa Species 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 239000005596 Picolinafen Substances 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 239000005986 Prohexadione Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Natural products C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 240000001451 Rottboellia cochinchinensis Species 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 241001302809 Schoenoplectus triqueter Species 0.000 description 1
- 244000085269 Scirpus juncoides Species 0.000 description 1
- 244000010062 Setaria pumila Species 0.000 description 1
- 235000002248 Setaria viridis Nutrition 0.000 description 1
- 241000220261 Sinapis Species 0.000 description 1
- 235000002597 Solanum melongena Nutrition 0.000 description 1
- 244000061458 Solanum melongena Species 0.000 description 1
- 235000007230 Sorghum bicolor Nutrition 0.000 description 1
- 244000046109 Sorghum vulgare var. nervosum Species 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000005622 Thiencarbazone Substances 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 102000004357 Transferases Human genes 0.000 description 1
- 108090000992 Transferases Proteins 0.000 description 1
- 108700019146 Transgenes Proteins 0.000 description 1
- 241000972221 Urochloa decumbens Species 0.000 description 1
- 241000044594 Urochloa plantaginea Species 0.000 description 1
- 241001141210 Urochloa platyphylla Species 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- ROMMVUMWISCVBE-UHFFFAOYSA-N [F].N#CC#N Chemical compound [F].N#CC#N ROMMVUMWISCVBE-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- QLVHFTGKDGTJDH-UHFFFAOYSA-N acetic acid;ethenyl acetate Chemical compound CC(O)=O.CC(=O)OC=C QLVHFTGKDGTJDH-UHFFFAOYSA-N 0.000 description 1
- 239000012445 acidic reagent Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000004647 alkyl sulfenyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 125000002393 azetidinyl group Chemical group 0.000 description 1
- 229940097012 bacillus thuringiensis Drugs 0.000 description 1
- 238000000498 ball milling Methods 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- HYJSGOXICXYZGS-UHFFFAOYSA-N benazolin Chemical compound C1=CC=C2SC(=O)N(CC(=O)O)C2=C1Cl HYJSGOXICXYZGS-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 229920002988 biodegradable polymer Polymers 0.000 description 1
- 239000004621 biodegradable polymer Substances 0.000 description 1
- 239000003124 biologic agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000010170 biological method Methods 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- 244000022203 blackseeded proso millet Species 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- NNBFNNNWANBMTI-UHFFFAOYSA-M brilliant green Chemical compound OS([O-])(=O)=O.C1=CC(N(CC)CC)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](CC)CC)C=C1 NNBFNNNWANBMTI-UHFFFAOYSA-M 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 150000004648 butanoic acid derivatives Chemical class 0.000 description 1
- JIJAYWGYIDJVJI-UHFFFAOYSA-N butyl naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)OCCCC)=CC=CC2=C1 JIJAYWGYIDJVJI-UHFFFAOYSA-N 0.000 description 1
- LGFPDDKHVBSPBT-UHFFFAOYSA-N butyl(methylidyne)azanium Chemical compound CCCC[N+]#C LGFPDDKHVBSPBT-UHFFFAOYSA-N 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 125000005588 carbonic acid salt group Chemical group 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 235000019504 cigarettes Nutrition 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- BIKACRYIQSLICJ-UHFFFAOYSA-N cloransulam-methyl Chemical group N=1N2C(OCC)=NC(F)=CC2=NC=1S(=O)(=O)NC1=C(Cl)C=CC=C1C(=O)OC BIKACRYIQSLICJ-UHFFFAOYSA-N 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 239000011162 core material Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- 238000009795 derivation Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 235000013325 dietary fiber Nutrition 0.000 description 1
- 150000002012 dioxanes Chemical class 0.000 description 1
- ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 239000004491 dispersible concentrate Substances 0.000 description 1
- 238000009837 dry grinding Methods 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- SFNALCNOMXIBKG-UHFFFAOYSA-N ethylene glycol monododecyl ether Chemical compound CCCCCCCCCCCCOCCO SFNALCNOMXIBKG-UHFFFAOYSA-N 0.000 description 1
- 241001233957 eudicotyledons Species 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000009313 farming Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 235000003642 hunger Nutrition 0.000 description 1
- 238000009396 hybridization Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 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 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 229940030980 inova Drugs 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000010977 jade Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 150000005451 methyl sulfates Chemical class 0.000 description 1
- 229950000081 metilsulfate Drugs 0.000 description 1
- 239000011785 micronutrient Substances 0.000 description 1
- 235000013369 micronutrients Nutrition 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical class CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 1
- 125000006095 n-butyl sulfinyl group Chemical group 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006124 n-propyl sulfonyl group Chemical group 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 230000000050 nutritive effect Effects 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000004893 oxazines Chemical class 0.000 description 1
- 150000002921 oxetanes Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- CWKFPEBMTGKLKX-UHFFFAOYSA-N picolinafen Chemical compound C1=CC(F)=CC=C1NC(=O)C1=CC=CC(OC=2C=C(C=CC=2)C(F)(F)F)=N1 CWKFPEBMTGKLKX-UHFFFAOYSA-N 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000004476 plant protection product Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BUCOQPHDYUOJSI-UHFFFAOYSA-N prohexadione Chemical compound CCC(=O)C1C(=O)CC(C(O)=O)CC1=O BUCOQPHDYUOJSI-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
- OVPLZYJGTGDFNB-UHFFFAOYSA-N propan-2-yl carbamate Chemical class CC(C)OC(N)=O OVPLZYJGTGDFNB-UHFFFAOYSA-N 0.000 description 1
- IVRIRQXJSNCSPQ-UHFFFAOYSA-N propan-2-yl carbonochloridate Chemical compound CC(C)OC(Cl)=O IVRIRQXJSNCSPQ-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- DWSPRBSLSXQIEJ-UHFFFAOYSA-N pyrasulfotole Chemical compound CC1=NN(C)C(O)=C1C(=O)C1=CC=C(C(F)(F)F)C=C1S(C)(=O)=O DWSPRBSLSXQIEJ-UHFFFAOYSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- IIVUJUOJERNGQX-UHFFFAOYSA-N pyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=CN=C1 IIVUJUOJERNGQX-UHFFFAOYSA-N 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000035040 seed growth Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 229940084106 spermaceti Drugs 0.000 description 1
- 239000012177 spermaceti Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229960005137 succinic acid Drugs 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940104261 taurate Drugs 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- GLDAZAQRGCSFNP-UHFFFAOYSA-N thiencarbazone Chemical compound O=C1N(C)C(OC)=NN1C(=O)NS(=O)(=O)C1=C(C)SC=C1C(O)=O GLDAZAQRGCSFNP-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 description 1
- 238000003971 tillage Methods 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- AISMNBXOJRHCIA-UHFFFAOYSA-N trimethylazanium;bromide Chemical compound Br.CN(C)C AISMNBXOJRHCIA-UHFFFAOYSA-N 0.000 description 1
- 239000004560 ultra-low volume (ULV) liquid Substances 0.000 description 1
- 241001478887 unidentified soil bacteria Species 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000010792 warming Methods 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- 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
-
- 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
- A01N43/74—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
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- 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
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/20—N-Aryl derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/22—O-Aryl or S-Aryl esters thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D403/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- C07D417/14—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 three or more hetero 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
- A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/46—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom rings with more than six members
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
本发明涉及除草活性的吡啶并‑/嘧啶并‑吡唑衍生物,连同涉及用于制备此类衍生物的方法和中间体。本发明进一步延伸到包括此类衍生物的除草组合物,连同延伸到此类化合物和组合物在有用植物的作物中控制不希望的植物生长中的用途,特别是在控制杂草中的用途。
Description
本发明涉及除草活性的吡啶并-/嘧啶并-吡唑衍生物,连同涉及用于制备此类衍生物的方法和中间体。本发明进一步延伸到包括此类衍生物的除草组合物,连同延伸到此类化合物和组合物在有用植物的作物中控制不希望的植物生长中的用途,特别是在控制杂草中的用途。
除草嘧啶并-咪唑是从WO 2005/047281已知的。在WO 2013/162715、WO 2013/162716、WO 2013/062981和WO 2012/061290中描述了用作杀螨/杀昆虫/杀软体动物/杀线虫剂或用于在控制无脊椎动物害虫中的吡啶并-/嘧啶并-吡唑衍生物。
本发明是基于以下发现:如在本文所定义的具有化学式(I)的吡啶并-吡唑和嘧啶并-吡唑衍生物展示了出人意料地良好的除草活性。
因此,在本发明的第一个方面,提供了具有化学式(I)的化合物,
或其盐或N-氧化物作为除草剂的用途,其中Q是选自
的环系统,其中A表示与杂芳基环的附接点,以及B表示与氮原子的附接点;
X1是N或CR1;
R1是氢、卤素、氰基、C1-C6烷基、C3-C6环烷基、C2-C6烯基、C2-C6炔基、C1-C6烷氧基、C(O)OR6或S(O)n(C1-C6烷基)、甲酰基、羟基、-C(O)NR6R7、NR6R7、苄氧基、C1-C6卤代烷氧基或C1-C6卤代烷基;
R2是氢、卤素、氰基、硝基、C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、C(O)OR6、或S(O)n(C1-C6烷基)、C1-C6烷氧基、C1-C6卤代烷氧基;
n是0、1、或2;
R3是氢、氰基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C2-C6卤代烯基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6卤代烷氧基、C2-C6烯氧基、C3-C10环烷基、NR6R7;
R4是O、S、或N(C1-C6烷基);
X2是O、S、或NR8;
R5是氢,C1-C6烷基,C2-C6烯基,C2-C6炔基,C3-C10环烷基,C3-C10环烯基,C1-C6卤代烷基,C2-C6卤代烯基,C1-C6烷氧基,C1-C6卤代烷氧基,C2-C6烯氧基,C2-C6炔氧基,C3-C10环烷氧基,C3-C10环烯氧基,C2-C6卤代烯氧基,C6-C10芳基或被从1至3个独立地选自卤素、硝基、氰基、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基和C1-C3卤代烷氧基的基团取代的C6-C10芳基;C3-C10杂环基或被从1至3个独立地选自卤素、硝基、氰基、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基、和C1-C3卤代烷氧基的基团取代的C3-C10杂环基;或NR6R7;
或R3和R5连同X2以及它们所连接的原子一起形成饱和或部分不饱和5-9元环系统,该5-9元环系统任选地包括1至3个独立地选自S、O和N的杂原子并且任选地被1至3个独立地选自卤素或C1-C6烷基的基团取代;
或R3和R8连同它们所连接的原子一起形成饱和或部分不饱和5-9元环系统,该5-9元环系统任选地包括1至3个独立地选自S、O和N的杂原子并且任选地被1至3个独立地选自卤素或C1-C6烷基的基团取代;
R6和R7各自独立地是氢、C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、或C2-C6炔基,
或R6和R7连同它们所连接的氮原子一起形成饱和或部分不饱和3-6元环,该3-6元环任选地包括1至3个独立地选自S、O和N的杂原子并且任选地被1至3个独立地选自卤素或C1-C6烷基的基团取代;
R8是氢、氰基、C1-C6烷基、C1-C6卤代烷基、C2-C6烯基或C2-C6炔基;C1-C6烷氧基、C1-C6卤代烷氧基、C2-C6烯氧基、C2-C6炔氧基、C3-C10环烷基氧基、C3-C10环烯氧基、C2-C6卤代烯氧基;
或R7和R8连同它们所连接的碳原子一起形成饱和或部分不饱和3-9元环,该3-9元环任选地包括1至3个独立地选自S、O和N的杂原子并且任选地被1至3个独立地选自卤素或C1-C6烷基的基团取代,
R9是氢、卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、C2-C6炔基、C1-C6卤代烷氧基、C1-C6烷氧基、或C3-C6环烷基;
R10是氢、C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6烷基硫基、-C(O)OR6、C1-C6烷氧基、C1-C6卤代烷氧基、C3-C6环烷基、或C2-C6炔基。
具有化学式(I)的化合物可以作为不同的几何异构体或以不同的互变异构的形式存在。本发明涵盖了所有的此类异构体和互变异构体,以及它们的处于所有比例的混合物,连同同位素形式(例如氘化的化合物)的用途。
可能的情况是具有化学式(I)的化合物包含一个或多个不对称中心并且因此可以产生光学异构体和非对映异构体。尽管没有相对于立体化学示出,本发明包括所有此类光学异构体和非对映异构体连同外消旋的和拆分的对映异构体纯的R和S立体异构体以及这些R和S立体异构体的其他混合物及其农用化学上可接受的盐的用途。
每个烷基部分单独或者作为较大基团(如烷氧基、烷硫基、烷氧基羰基、烷基羰基、烷氨基羰基或二烷氨基羰基等)的一部分可以是直链或支链的。典型地,该烷基是例如甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、正戊基、新戊基、或正己基。烷基基团通常是C1-C6烷基基团(除了在已经更狭窄地定义时),但优选地是C1-C4烷基或C1-C3烷基基团,并且更优选地是C1-C2烷基基团(例如甲基)。
烯基和炔基部分可以处于直链或支链的形式,并且这些烯基部分适当时可以是具有(E)-或(Z)-构型。烯基和炔基部分可以含有一个或多个任何组合的双和/或三键,但优选地含有仅一个双键(对于烯基来说)或仅一个三键(对于炔基来说)。
烯基或炔基部分典型地是C2-C4烯基或C2-C4炔基,更具体地是乙烯基(ethenyl)(乙烯基(vinyl))、丙-2-烯基(烯丙基)、乙炔基、丙-2-炔基(炔丙基)、或丙-1-炔基。
优选地,术语环烷基是指环丙基、环丁基、环戊基或环己基。
在本说明书的背景下,术语“芳基”优选地意指苯基。如在此所用,术语“杂芳基”意指包含至少一个环杂原子并且由单环组成的芳香族环系统。优选地,单环将包含独立地选自氮、氧以及硫的1、2或3个杂原子。典型地,“杂芳基”是呋喃基、噻吩基、吡咯基、吡唑基、咪唑基、1,2,3-三唑基、1,2,4-三唑基、噁唑基、异噁唑基、噻唑基、异噻唑基、1,2,4-噁二唑基、1,3,4-噁二唑基、1,2,5-噁二唑基、1,2,3-噻二唑基、1,2,4-噻二唑基、1,3,4-噻二唑基、1,2,5-噻二唑基、吡啶基、嘧啶基、哒嗪基、吡嗪基、1,2,3-三嗪基、1,2,4-三嗪基、或1,3,5-三嗪基。
杂环基基团以及杂环(单独的或作为更大基团(例如杂环基-烷基-)的部分)是包含至少一个杂原子的环系统并且可以是处于单环或双环形式。优选地,杂环基基团将包含多达两个杂原子,这些杂原子将优选地选自氮、氧以及硫。杂环基团的实例包括氧杂环丁烷基、硫杂环丁烷基、氮杂环丁烷基以及7-氧杂-双环[2.2.1]庚-2-基。包含单个氧原子作为杂原子的杂环基基团是最优选的。杂环基基团优选地是3元至8元环,更优选地3元至6元环。
卤素(或卤代)涵盖了氟、氯、溴或碘。该卤素对应地应用于其他定义背景下的卤素,如卤代烷基或卤代苯基。
具有从1至6个碳原子链长的卤代烷基基团是,例如氟甲基、二氟甲基、三氟甲基、氯甲基、二氯甲基、三氯甲基、2,2,2-三氟乙基、2-氟乙基、2-氯乙基、五氟乙基、1,1-二氟-2,2,2-三氯乙基、2,2,3,3-四氟乙基、2,2,2-三氯乙基、七氟正丙基以及全氟正己基。
烷氧基基团优选地具有从1至6个碳原子的链长。烷氧基是,例如甲氧基、乙氧基、丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基或叔丁氧基或戊氧基或己氧基异构体,优选地是甲氧基和乙氧基。还应当领会的是,两个烷氧基取代基可以存在于相同碳原子上。
卤代烷氧基是,例如氟甲氧基、二氟甲氧基、三氟甲氧基、2,2,2-三氟乙氧基、1,1,2,2-四氟乙氧基、2-氟乙氧基、2-氯乙氧基、2,2-二氟乙氧基或2,2,2-三氯乙氧基,优选地二氟甲氧基、2-氯乙氧基或三氟甲氧基。
C1-C6烷基-S-(烷基硫基)是,例如甲硫基、乙硫基、正丙硫基、异丙硫基、正丁硫基、异丁硫基、仲丁硫基或叔丁硫基,优选地是甲硫基或乙硫基。
C1-C6烷基-S(O)-(烷基亚磺酰基)是,例如甲基亚磺酰基、乙基亚磺酰基、正丙基亚磺酰基、异丙基亚磺酰基、正丁基亚磺酰基、异丁基亚磺酰基、仲丁基亚磺酰基或叔丁基亚磺酰基,优选地是甲基亚磺酰基或乙基亚磺酰基。
C1-C6烷基-S(O)2-(烷基磺酰基)是,例如甲基磺酰基、乙基磺酰基、正丙基磺酰基、异丙基磺酰基、正丁基磺酰基、异丁基磺酰基、仲丁基磺酰基或叔丁基磺酰基,优选地是甲基磺酰基或乙基磺酰基。
具有化学式(I)的化合物可以与胺类(例如,氨水、二甲胺和三乙胺)、碱金属和碱土金属碱类或季铵碱类形成,和/或用作农学上可接受的盐。在用作成盐物的碱金属和碱土金属氢氧化物、氧化物、醇化物以及碳酸氢盐和碳酸盐之中,要强调的是锂、钠、钾、镁和钙的氢氧化物、醇化物、氧化物以及碳酸盐,但尤其是钠、镁和钙的那些。还可以使用对应的三甲基锍盐。
当具有化学式(I)的化合物含有碱部分时,该具有化学式(I)的化合物还可以与各种有机和/或无机酸(例如乙酸、丙酸、乳酸、柠檬酸、酒石酸、琥珀酸、富马酸、马来酸、丙二酸、扁桃酸、苹果酸、邻苯二甲酸、盐酸、氢溴酸、磷酸、硝酸、硫酸、甲磺酸、萘磺酸、苯磺酸、甲苯磺酸、樟脑磺酸以及类似地已知可接受的酸)形成(和/或用作)农学上可接受的盐。
具有化学式(I)的化合物还可以是/用作成盐过程中形成的水合物形式。
X1、X2、R1、R2、R3、R4、R5、R6、R7、R8、R9、R10以及n的优选值是如以下列出的,并且根据本发明的具有化学式(I)的化合物可以包括所述值的任何组合。熟练的技术人员将理解,用于任何指定组的实施例的值可以与用于任何其他组的实施例的值组合,其中这些组合不相互排斥。
优选地,R1是氢、卤素、甲酰基、氰基、C1-C6烷氧基、C1-C6烷基磺酰基、C1-C6烷基硫基、C1-C6卤代烷氧基、-C(O)NR6R7、NR6R7、或C1-C6卤代烷基。更优选地,R1是氢、氟、氯、氰基、三氟甲基、甲氧基、二氟甲氧基、甲酰基、甲烷磺酰基、甲酰胺、甲硫醇或氨基。
优选地,R2是卤素、氰基、硝基、C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6烷基硫基、-C(O)OR6、C1-C6烷氧基、C1-C6卤代烷氧基、C3-C6环烷基、或C2-C6炔基。更优选地,R2是卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、C1-C6烷氧基、C1-C6卤代烷氧基、C3-C6环烷基、-C(=O)OR6、或C2-C6炔基。甚至更优选地,R2是甲基、三氟甲基、氯、溴、碘、氟、乙烯基、乙炔基、甲氧基羰基、-CO2H、或环丙基;
如上所述,R3是C1-C6烷基、C2-C6烯基、C2-C6炔基、C2-C6卤代烯基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6卤代烷氧基、C2-C6烯氧基、C3-C10环烷基、或NR6R7。优选地,R3是氢、或C1-C3烷基。更优选地,R3是氢或甲基。
优选地,R4是O。
优选地,X2是O、或NR8。
优选地,R5是C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C10环烷基、C1-C6卤代烷基、C2-C6卤代烯基、C1-C6烷氧基、C1-C6卤代烷氧基、C2-C6烯氧基、C2-C6炔氧基、C3-C10环烷氧基、C3-C10环烯氧基、C2-C6卤代烯氧基、C6-C20芳基、C3-C20杂环基、或NR6R7。更优选地,R5是甲基、乙基、异丙基、叔丁基或叔丁氧基。
优选地,R8是氢、氰基、C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、或C2-C6炔基。
优选地R9是氢、氯、氟、溴、甲基或三氟甲基。更优选地,R9是氢、氯、氟、或溴。甚至更优选地,R9是氢、或氯。
优选地,R10是C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6烷基硫基、-C(O)OR6、C1-C6烷氧基、C1-C6卤代烷氧基、C3-C6环烷基、或C2-C6炔基。更优选地,R10是C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、C1-C6烷氧基、C1-C6卤代烷氧基、C3-C6环烷基、-C(O)OR6、或C2-C6炔基。甚至更优选地R10是甲基、三氟甲基或二氟甲基。
在实施例中(其中R3和R5,连同X2以及它们所连接的原子一起形成饱和或部分不饱和5-9元环系统,该5-9元环系统任选地包括1至3个独立地选自S、O和N的杂原子并且任选地被1至3个独立地选自卤素或C1-C6烷基的基团取代),优选的是形成以下基团T(即T1或T2):
其中X2和R4是如本文所定义的,并且A表示与吡啶并/嘧啶并-吡唑部分的附接点。优选地,在基团T1和T2中,R4是O并且X2是O或NR8。甚至更优选地,R4是O并且X2是O或NR8,并且R8是甲基。
下表1提供了用于根据本发明所述的用途的具有化学式(I)的除草化合物的具体实例。
表1具有化学式(I)的化合物
具有化学式(I)的化合物可以使用有机化学领域中技术人员已知的技术,根据以下方案进行制备,其中取代基X1、X2、R1、R2、R3、R4、R5、R6、R7、R8、R9、R10和n具有(除非另有明确说明)上文所描述的定义。下文描述了用于生产具有化学式(I)的化合物的通用方法。除非在本文中另外说明,否则该合成方法源自WO 2013/162715、WO 2013/162716、WO 2013/062981和WO 2012/061290。用于制备本发明的化合物的起始材料可以购买自通常的商品供应商或者可以由已知的方法制备。起始材料以及中间体可以在使用前,通过现有技术的方法说明(例如层析、结晶、蒸馏和过滤)进行纯化。
方案1
如上述方案1所示,在合适的碱(如氢化钠)和合适的溶剂(如DMSO)存在下,用二硫化碳和碘甲烷处理经适当取代的具有化学式(II)的杂环甲基酮可以得到具有化学式(III)的化合物。可以在碱(如三乙胺)存在下,在溶剂(如乙醇)中,用合适的具有化学式(XXXII)的胺处理具有化学式(III)的化合物,以提供具有化学式(IV)的化合物和/或他们的立体异构体。
可以通过如WO 2013/162716中所述,在极性质子溶剂(如乙醇)中,用适当经取代的具有化学式(XXX)的肼进行处理,将具有化学式(IV)的化合物进一步转化成具有化学式(V)的氨基吡唑。可以在非质子溶剂(例如二氯甲烷)中或在使用过量的碱(例如吡啶)作为溶剂来得到具有化学式(Ib)的化合物的条件下,在合适的碱(例如吡啶)存在下,通过与合适的具有化学式(XXXI)的试剂(其中LG是合适的离去基团(例如,该试剂(XXXI)是二碳酸二叔丁酯))反应,对得到的具有化学式(V)的氨基吡唑进行进一步加工。
作为替代方案,当R9=H时,可以在合适的溶剂(如乙腈)中,用合适的试剂(如N-氯代琥珀酰亚胺)对具有化学式(V)的化合物进行卤化,得到具有化学式(VI)的化合物,其进而可以在非质子溶剂(例如二氯甲烷)中或在使用过量的碱(例如吡啶)作为溶剂来得到(Ib)的条件下,在合适的碱(例如吡啶)存在下,通过与合适的具有化学式(XXXI)的试剂(例如,二碳酸二叔丁酯)反应进行进一步加工。
如下面方案2中所示,具有化学式(Ib)的化合物可以经由起始于β-二酮酸酯(例如2,4-二氧代-4-(3-吡啶基)丁酸乙酯)的序列进行制备,其中该二酮酸酯可以通过在合适的碱(例如氢化钠)存在下,在合适的溶剂(例如THF)中,将适当取代的具有化学式(II)的杂芳基酮与草酸二酯(例如草酸二乙酯)缩合来制备。
具有化学式(VII)的β-二酮酸酯可以与适当取代的具有化学式(XXX)的肼在极性质子溶剂(如乙醇)中反应,以给出具有化学式(VIII)的吡嗪酯。在典型条件(例如氢氧化钠,水和1,4-二噁烷)下进行碱性皂化,然后根据需要分离,得到具有化学式(IX)的酸,该酸可以与合适的试剂(如二苯基磷酰叠氮化物(DPPA))反应形成酰基叠氮化物,该酰基叠氮化物经历原位库尔修斯反应,以产生异氰酸酯,然后用合适的具有化学式(XXXIII)的醇(X2=O)淬灭该异氰酸酯,得到具有化学式(Ic)的氨基甲酸酯。然后可以在温和条件下(使用例如在极性非质子溶剂如N,N-二甲基甲酰胺中氢化钠)用合适的具有化学式(XXXIV)的烷基化剂进一步烷基化这些氨基甲酸酯,其中LG是合适的离去基团(这样的烷基化试剂的实例是甲基碘),得到具有化学式(Ib)的化合物。
方案2
如上面方案3所示,制备具有化学式(Ib)的化合物的另一种方法是通过具有化学式(X)的化合物(其可以通过各种已知方法制备,包括但不限于,由Ridge等人在J.Med.Chem.1979,22,1385-1389[药物化学杂志1979,22,1385-1389]中描述的那些)。具有化学式(X)的化合物可以与合适的具有化学式(XXX)的肼缩合,得到具有化学式(XI)的区域异构的氨基吡唑。
在非质子溶剂(例如二氯甲烷)中或在使用过量的碱(例如吡啶)作为溶剂的条件下在合适的碱(例如吡啶)存在下,可以将所得到的具有化学式(XI)的氨基吡唑通过与具有化学式(XXXI)的合适试剂(如二碳酸二叔丁基酯)反应来进行进一步加工,来提供具有化学式(Ic)的化合物(分离形成的产品混合物之后)即,本发明所述化合物的实例,其中R3=H)。在典型的极性非质子溶剂(如N,N-二甲基甲酰胺)中,用合适的碱(例如氢化钠)去质子化后,用合适的具有化学式(XXXIV)的亲电子试剂(如甲基碘)进行烷基化,产生具有化学式(Ib)的化合物。
方案3
如方案4所示,在合适的碱存在下和在合适的溶剂中,通过用具有化学式(XLI)的化合物(其中LG是合适的离去基团,例如Cl,Br,I或OT)进行烷基化,可以可替代地由具有化学式(XIa)的氨基吡唑(具有化学式XI的化合物,其中R10=H)制备具有化学式(XI)的氨基吡唑(其中R10≠H)。合适的溶剂/碱组合包括Cs2CO3/DMF(参见例如M.K.Ameriks等人,生物有机与药物化学快报(2009),613[Bioorg.Med.Chem,Lett.(2009),613])和KOH/丙酮(参见例如G.Guillaumet等人,Bioorg.Med.Chem.Lett.(2006),1078[生物有机与药物化学快报(2006),1078])。
方案4
如方案5所示,如在WO 2013/062981中所传授的,可以在极性质子溶剂(如乙醇)中,使用氢气、合适的催化剂(例如氧化铝上的5%Pd)和酸溶液(例如50%HBr),在氢化条件下,将具有化学式(XII)的化合物的硝基官能度还原成胺,得到具有化学式(XIII)的化合物(其可作为盐(例如HBr盐)被分离)。
在溶剂(如水/THF)和合适的碱(如碳酸氢钠)的混合物存在下,可以使用合适的具有化学式(XXXI)的试剂(如二碳酸二叔丁酯)将具有化学式(XIII)的化合物转化成具有化学式(XIIV)的化合物。
如在WO 2013/062981中所传授的,在具有合适碱(如磷酸钾)的极性非质子溶剂(如乙腈)中,在催化量的氯化铜(II)与配体(如N,N'-二甲基乙烷-1,2-二胺)的存在下,可以通过与具有化学式(XV)的化合物反应,将具有化学式(XIIV)的化合物进一步转化成具有化学式(Id)的化合物,得到具有化学式(Id)的化合物,该所得化合物为本发明所述化合物,其中R3=H。在极性非质子溶剂(如N,N-二甲基甲酰胺)中,用具有化学式(XXXIV)的合适的烷基化剂(如甲基碘)和合适的碱进一步烷基化产生具有化学式(Ia)的化合物。
方案5
如在方案6中所示,当R4=O,X2=O以及R5=t-Bu时,在温和的酸性条件下(例如,用在醚中的HCl),可以将所得到的N-Boc基团去除,以提供胺盐,例如HCl盐。具有化学式(I)的化合物的酸性裂解(例如用溶剂如四氢呋喃中的HCl)得到具有化学式(XVI)的化合物作为其盐,例如作为其HCl盐。然后可以在碱(例如吡啶)存在下,通过与合适的具有化学式(XXXV)的氯甲酸酯(如氯甲酸乙酯)反应,将具有化学式(XVI)的化合物进一步转化为例如具有化学式(If)的化合物。
方案6
作为替代方案,然后可以通过与碳酰氯或具有化学式(XXXVII)的适合的碳酰氯等效物(如CDI或4-硝基苯基氯甲酸酯)反应,进一步转化具有化学式(XVI)的化合物,以给出具有化学式(Ie)的化合物。然后与具有化学式(XXXIII)的醇、胺或硫醇进一步反应,得到具有化学式(Ig)的化合物。
作为另外的替代方案,可以通过与合适的具有化学式(XXXVI)的异氰酸酯(例如叔丁基-异腈)反应,将具有化学式(XVI)的化合物转化为例如具有化学式(Ih)的化合物。当X2=N,可以在碱(例如碳酸钾)存在下,用合适的具有化学式(XXXVIII)的亲电子试剂(例如甲基碘)进一步烷基化具有化学式(Ih)的化合物,以给出具有化学式(Ii)的化合物。
方案7
如方案7所示,如在WO 2013/186089中所传授的,可以在溶剂如(1,4-二噁烷)中,通过用具有化学式(XXXIX)的双功能试剂(例如1-氯-2-异硫氰酸基乙烷或1-溴-4-异氰酸基合丁烷)处理,将具有化学式(XVI)的化合物转化为具有化学式(Ik)的化合物。
方案8
如方案8所示,在醚溶剂(如1,4-二噁烷)中,将具有化学式(Ip)的化合物用具有化学式(XX)的双官能试剂(例如氯甲酸氯乙酯)以及碱(例如氢化钠)进行酰化,得到具有化学式(XXI)的化合物。可以在溶剂(如二氯甲烷)中,用酸性试剂(如TFA),在温和条件下裂解N-Boc基团,以得到具有化学式(Ip)的化合物。
经由在极性非质子溶剂(例如N,N-二甲基甲酰胺)中用合适的碱(例如氢化钠)去质子化,通过环化对具有化学式(Ip)的化合物进一步官能化,以得到具有化学式(Iq)的化合物。
如本文所描述的具有化学式(I)的化合物可以自身被用作除草剂,但是通常使用配制佐剂(例如载体、溶剂和表面活性剂(SFA))将它们配制成除草组合物。因此,本发明进一步提供了包括如本文所描述的除草化合物和农业上可接受的配制佐剂的除草组合物。该组合物可以处于浓缩物的形式,在使用前稀释这些浓缩物,尽管也可以制成即用型组合物。通常用水进行最终稀释,但是可以替代水或除了水之外使用例如液体肥料、微量营养素、生物有机体、油或溶剂。
这些除草组合物总体上包含按重量计从0.1%到99%、尤其是按重量计从0.1%到95%的具有化学式(I)的化合物以及按重量计从1%到99.9%的配制佐剂,该配制佐剂优选地包括按重量计从0%到25%的表面活性物质。
这些组合物可以选自多种配制品类型,这些配制品类型中的很多从《关于植物保护产物的FAO标准的发展和使用的手册》(Manual on Development and Use of FAOSpecifications for Plant Protection Products),第5版,1999年中得知。这些包括可尘化粉剂(DP)、可溶性粉剂(SP)、水溶性颗粒剂(SG)、水可分散性颗粒剂(WG)、可湿性粉剂(WP)、颗粒剂(GR)(缓释或快释的)、可溶的浓缩物(SL)、油易混合的液体(OL)、超低体积液体(UL)、可乳化的浓缩物(EC)、可分散性浓缩物(DC)、乳液(水包油(EW)和油包水(EO)两者)、微乳液(ME)、悬浮液浓缩物(SC)、气溶胶、胶囊悬浮液(CS)以及种子处理配制品。在任何情况下,所选择的配制品类型将取决于所设想的具体目的以及具有化学式(I)的化合物的物理、化学和生物特性。
可尘化粉剂(DP)可以通过将具有化学式(I)的化合物与一种或多种固体稀释剂(例如,天然粘土、高岭土、叶蜡石、膨润土、氧化铝、蒙脱石、硅藻土(kieselguhr)、白垩土、硅藻土(diatomaceous earths)、磷酸钙、碳酸钙和碳酸镁、硫、石灰、面粉、滑石和其他有机和无机的固体载体)混合并将该混合物机械地碾磨成细粉末来制备。
可溶性粉剂(SP)可以通过将具有化学式(I)的化合物与一种或多种水-溶性无机盐(如碳酸氢钠、碳酸钠或硫酸镁)或一种或多种水溶性有机固体(如多糖)以及任选地一种或多种湿润剂、一种或多种分散剂或所述试剂的混合物进行混合来制备以改进水分散性/水溶性。然后将该混合物研磨成细粉末。也可以将类似的组合物颗粒化以形成水溶性颗粒剂(SG)。
可湿性粉剂(WP)可以通过将具有化学式(I)的化合物与一种或多种固体稀释剂或载体、一种或多种湿润剂以及优选地,一种或多种分散剂,以及优选地,一种或多种的悬浮剂混合来制备以促进在液体中的分散。然后将该混合物研磨成细粉末。也可以将类似的组合物颗粒化以形成水可分散性颗粒剂(WG)。
可以这样形成颗粒剂(GR):通过将具有化学式(I)的化合物与一种或多种粉状固体稀释剂或载体的混合物造粒来形成,或者通过将具有化学式(I)的化合物(或其在适宜试剂中的溶液)吸收进多孔颗粒材料(例如浮石、凹凸棒石粘土、漂白土、硅藻土(kieselguhr)、硅藻土(diatomaceous earths)或玉米芯粉),或通过将具有化学式(I)的化合物(或其在适宜试剂中的溶液)吸附到硬芯材料(例如沙、硅酸盐、矿物碳酸盐、硫酸盐或磷酸盐)上并且如果必要的话,进行干燥来由预成型的空白颗粒形成。通常用于帮助吸收或吸附的试剂包括溶剂(如脂肪族和芳香族石油溶剂、醇、醚、酮以及酯)和粘着剂(如聚乙酸乙烯酯、聚乙烯醇、糊精、糖以及植物油)。一种或多种其他添加剂还可以包括在颗粒(例如乳化剂、湿润剂或分散剂)。
可分散的浓缩物(DC)可以通过将具有化学式(I)的化合物溶于水或有机溶剂(如酮、醇或乙二醇醚)中来制备。这些溶液可以包含表面活性剂(例如以改进水稀释或防止喷雾罐中的结晶)。
可乳化的浓缩物(EC)或水包油乳液(EW)可以通过将具有化学式(I)的化合物溶于有机溶剂(任选地包含一种或多种湿润剂、一种或多种乳化剂或者所述试剂的混合物)中来制备。在EC中使用的适合的有机溶剂包括芳香族烃类(如烷基苯或烷基萘,例如SOLVESSO100、SOLVESSO 150和SOLVESSO 200;SOLVESSO是注册商标)、酮类(如环己酮或甲基环己酮)和醇类(如苯甲醇、糠醇或丁醇)、N-烷基吡咯烷酮类(如N-甲基吡咯烷酮或N-辛基吡咯烷酮)、脂肪酸的二甲基酰胺(如C8-C10脂肪酸二甲基酰胺)和氯化烃类。EC产品可以在添加到水中时自发地乳化,从而产生具有足够稳定性的乳液,以允许通过适当设备进行喷洒施用。
EW的制备涉及获得作为液体(如果它在室温下不是液体,则它可以在典型地低于70℃的合理温度下熔化)或处于溶液中(通过将它溶于适当的溶剂中)的具有化学式(I)的化合物,然后在高剪切下将所得液体或溶液乳化进包含一种或多种SFA的水中,以产生乳液。在EW中使用的适合的溶剂包括植物油、氯化烃(如氯苯)、芳香族溶剂(如烷基苯或烷基萘)以及其他在水中具有低溶解度的适当的有机溶剂。
微乳液(ME)可以通过将水与一种或多种溶剂和一种或多种SFA的掺合物混合来制备,以自发地产生热力学稳定的各向同性的液体配制品。具有化学式(I)的化合物一开始就存在于水中或溶剂/SFA掺合物中。在ME中使用的适合的溶剂包括此前描述的在EC或EW中使用的那些。ME可以是水包油系统或油包水系统(存在哪种系统可以通过电导率测量来确定)并且可以适合用于在相同配制品中混合水溶性的和油溶性的杀有害生物剂。ME适合于稀释到水中,同时保持为微乳液或者形成常规的水包油乳液。
悬浮浓缩物(SC)可以包括具有化学式(I)的化合物的精细分散的不溶固体颗粒的水性或非水性悬浮液。SC可以任选地使用一种或多种分散剂通过在适合的介质中球磨或珠磨具有化学式(I)的固体化合物来制备,以产生该化合物的精细颗粒悬浮液。在该组合物中可以包括一种或多种湿润剂,并且可以包括悬浮剂以降低颗粒的沉降速率。可替代地,可以干磨具有化学式(I)的化合物并且将其添加到包含此前描述的试剂的水中,以产生希望的最终产物。
气溶胶配制品包含具有化学式(I)的化合物和适合的推进剂(例如,正丁烷)。还可将具有化学式(I)的化合物溶于或分散于适合的介质(例如水或可与水混溶的液体,如正丙醇)中以提供在不加压的手动喷雾泵中使用的组合物。
胶囊悬浮液(CS)可以通过以与制备EW配制品类似的方式来制备,除了附加的聚合步骤之外,这样使得获得油滴的水分散体,其中每个油滴都被聚合物外壳包裹并且含具有化学式(I)的化合物以及其可任选的载体或稀释剂。该聚合物壳可以通过界面缩聚反应或通过凝聚程序来制备。这些组合物可以提供具有化学式(I)的化合物的受控释放并且它们可以用于种子处理。具有化学式(I)的化合物也可以被配制在可生物降解的聚合物基质中,以提供该化合物的缓慢的控制释放。
该组合物可以包括一种或多种添加剂以改进该组合物的生物性能,例如通过改进表面上的湿润性、保留或分布;处理过的表面上的防雨性;或具有化学式(I)的化合物的吸收或迁移性。这样的添加剂包括表面活性剂(SFA)、基于油的喷雾添加剂,例如某些矿物油或天然植物油(例如大豆和油菜籽油),以及这些与其他生物增强佐剂(可帮助或修饰具有化学式(I)的化合物的作用的成分)的掺合物。
湿润剂、分散剂和乳化剂可以是阳离子类型、阴离子类型、两性类型或非-离子类型的SFA。
适合的阳离子类型的SFA包括季铵化合物(例如鲸蜡三甲基溴化铵)、咪唑啉以及胺盐。
适合的阴离子型SFA包括脂肪酸的碱金属盐、脂肪族硫酸单酯的盐(例如月桂硫酸钠)、磺化的芳香族化合物的盐(例如十二烷基苯磺酸钠、十二烷基苯磺酸钙、丁基萘磺酸盐以及二-异丙基-萘磺酸钠和三-异丙基-萘磺酸钠的混合物)、醚硫酸盐、醇醚硫酸盐(例如月桂醇聚醚-3-硫酸钠)、醚羧酸盐(例如月桂醇聚醚-3-羧酸钠)、磷酸酯类(来自一种或多种脂肪醇与磷酸(主要是单酯)或与五氧化二磷(主要是二酯)之间反应的产物,例如月桂醇与四磷酸之间的反应;另外这些产物可以被乙氧基化)、硫代琥珀酰胺酸盐、石蜡或烯烃磺酸盐、牛磺酸盐以及木质磺酸盐。
适合的两性型的SFA包括甜菜碱、丙酸盐和甘氨酸盐。
适合的非-离子型SFA包括环氧烷类(如环氧乙烷、环氧丙烷、环氧丁烷或其混合物)与脂肪醇类(如油醇或鲸蜡醇)或与烷基酚类(如辛基酚、壬基酚或辛基甲酚)的缩合产物;衍生自长链脂肪酸或己糖醇酐的偏酯;所述偏酯与环氧乙烷的缩合产物;嵌段聚合物(包含环氧乙烷和环氧丙烷);烷醇酰胺;单酯(例如脂肪酸聚乙二醇酯);氧化胺(例如月桂基二甲基氧化胺);以及卵磷脂。
适合的悬浮剂包括亲水性胶体(诸如多糖、聚乙烯吡咯烷酮或羧甲基纤维素钠)和膨胀性粘土(诸如膨润土或凹凸棒石)。
如本文所描述的除草组合物可以进一步包括至少一种另外的杀有害生物剂。例如,具有化学式(I)的化合物还可以与其他除草剂或植物生长调节剂组合使用。在优选的实施例中,该另外的杀有害生物剂是除草剂和/或除草剂安全剂。这类混合物的实例(其中‘I’代表具有化学式(I)的化合物)是:I+乙酰草胺、I+氟锁草醚、I+氟锁草醚钠、I+苯草醚、I+丙烯醛、I+甲草胺、I+阿洛昔芬、I+莠灭净、I+氨唑草酮、I+酰嘧磺隆、I+氯氨吡啶酸、I+杀草强、I+莎稗磷、I+黄草灵、I+莠去津、I+唑啶草酮、I+四唑嘧磺隆、I+BCPC、I+氟丁酰草胺、I+草除灵、I+苯卡巴腙、I+氟草胺、I+呋草磺、I+苄嘧磺隆、I+苄嘧磺隆甲酯、I+地散磷、I+灭草松、I+双苯嘧草酮、I+苯并双环酮、I+吡草酮、I+氟吡草酮、I+治草醚、I+双丙氨膦、I+双草醚、I+双草醚钠、I+硼砂、I+丁溴啶、I+溴丁酰草胺、I+溴草腈、I+丁草胺、I+丁胺磷、I+地乐胺、I+丁苯草酮、I+丁酸盐、I+卡可基酸、I+氯酸钙、I+唑草胺、I+长杀草、I+唑草酮、I+唑酮草酯、I+氯芴素、I+氯芴素甲酯、I+杀草敏、I+氯嘧磺隆、I+氯嘧磺隆乙酯、I+氯乙酸、I+绿麦隆、I+氯普芬、I+氯磺隆、I+敌草索、I+敌草索二甲酯、I+吲哚酮草酯、I+环庚草醚、I+醚磺隆、I+咯草隆、I+烯草酮、I+炔草酯、I+炔草酯炔丙酯、I+广灭灵、I+稗草胺、I+二氯吡啶酸、I+氯酯磺草胺、I+氯酯磺草胺甲酯、I+氰草津、I+环草敌、I+环丙嘧磺隆、I+噻草酮、I+氰氟草酯、I+氰氟草酯-丁基、I+2,4-D、I+杀草隆、I+茅草枯、I+棉隆、I+2,4-DB、I+甜菜安、I+麦草畏、I+敌草腈、I+2,4-滴丙酸、I+精2,4-滴丙酸、I+禾草灵、I+禾草灵甲酯、I+双氯磺草胺、I+野燕枯、I+野燕枯甲基磺酸盐、I+吡氟酰草胺、I+氟吡草腙、I+噁唑隆、I+哌草丹、I+二甲草胺、I+异戊净、I+二甲吩草胺、I+精二甲吩草胺、I+噻节因、I+二甲胂酸、I+敌乐胺、I+特乐酚、I+草乃敌、I+异丙净、I+敌草快、I+敌草快二溴化物、I+氟硫草定、I+敌草隆、I+草多索、I+EPTC、I+禾草畏、I+丁氟消草、I+胺苯磺隆、I+胺苯磺隆甲酯、I+乙烯利、I+甜菜呋、I+氟乳醚、I+乙氧嘧磺隆、I+乙氧苯草胺、I+精噁唑禾草灵、I+精噁唑禾草灵-乙酯、I+四唑酰草胺、I+硫酸亚铁、I+麦草氟M、I+啶嘧磺隆、I+双氟磺草胺、I+吡氟禾草灵、I+吡氟禾草灵丁酯、I+精吡氟禾草灵、I+精吡氟禾草灵-丁酯、I+异丙吡草酯、I+氟酮磺隆、I+氟酮磺隆-钠、I+氟吡磺隆、I+氟消草、I+氟噻草胺、I+氟哒嗪草酯、I+氟哒嗪草酯乙酯、I+氟节胺、I+唑嘧磺草胺、I+氟烯草酸、I+氟烯草酸戊酯、I+丙炔氟草胺、I+氟炔草胺(flumipropin)、I+伏草隆、I+乙羧氟草醚、I+乙羧氟草醚乙酯、I+氟虫腙(fluoxaprop)、I+氟胺草唑、I+氟替丙酸(flupropacil)、I+四氟丙酸、I+氟啶嘧磺隆、I+氟啶嘧磺隆-甲基-钠、I+抑草丁、I+氟啶草酮、I+氟咯草酮、I+使它隆、I+呋草酮、I+嗪草酸、I+嗪草酸甲酯、I+氟磺胺草醚、I+甲酰胺磺隆、I+蔓草磷、I+草铵膦、I+草铵膦铵、I+草甘膦、I+氟氯吡啶酯、I+氯吡嘧磺隆、I+氯吡嘧磺隆甲酯、I+吡氟氯禾灵、I+精吡氟氯禾灵、I+环嗪酮、I+咪草酯、I+咪草酯甲酯、I+甲氧咪草烟、I+甲咪唑烟酸、I+灭草烟、I+咪唑喹啉酸、I+咪草烟、I+咪唑磺隆、I+茚草酮、I+三嗪茚草胺、I+碘甲烷、I+碘磺隆、I+I+碘甲磺隆钠、I+碘苯腈、I+异丙隆、I+异噁隆、I+异噁酰草胺、I+异噁氯草酮、I+异噁唑草酮、I+异噁草醚、I+卡灵草、I+克阔乐、I+环草定、I+利谷隆、I+2甲4氯丙酸、I+精2甲4氯丙酸、I+苯噻酰草胺、I+氟磺酰草胺、I+甲基二磺隆、I+甲基二磺隆甲酯、I+硝磺草酮、I+威百亩、I+噁唑酰草胺、I+苯嗪草酮、I+吡草胺、I+甲基苯噻隆、I+灭草唑、I+甲基胂酸、I+甲基杀草隆、I+异硫氰酸甲酯、I+异丙甲草胺、I+S-异丙甲草胺、I+磺草唑胺、I+甲氧隆、I+赛克嗪、I+甲磺隆、I+甲磺隆甲酯、I+草达灭、I+绿谷隆、I+萘丙胺、I+敌草胺、I+抑草生、I+草不隆、I+烟嘧磺隆、I+正甲基草甘膦、I+壬酸、I+达草灭、I+油酸(脂肪酸)、I+坪草丹、I+嘧苯胺磺隆、I+氨磺灵、I+丙炔噁草酮、I+噁草酮、I+环氧嘧磺隆、I+噁嗪草酮、I+乙氧氟草醚、I+百草枯、I+百草枯二氯化物、I+克草猛、I+二甲戊乐灵、I+五氟磺草胺、I+五氯苯酚、I+甲氯酰草胺、I+环戊噁草酮、I+烯草胺、I+甜菜宁、I+毒莠定、I+氟吡酰草胺(picolinafen)、I+唑啉草酯、I+哌草磷、I+丙草胺、I+氟嘧磺隆、I+氟嘧磺隆甲酯、I+氨氟乐灵、I+环苯草酮、I+调环酸钙、I+扑灭通、I+扑草净、I+扑草胺、I+敌稗、I+喔草酯、I+扑灭津、I+苯胺灵、I+异丙草胺、I+丙苯磺隆、I+丙苯磺隆钠、I+拿草特、I+苄草丹、I+氟磺隆、I+双唑草腈、I+吡草醚、I+吡草醚乙酯、I+磺酰草吡唑(pyrasulfotole)、I+吡唑特、I+吡嘧磺隆、I+吡嘧磺隆乙酯、I+苄草唑(pyrazoxyfen)、I+嘧啶肟草醚、I+稗草畏、I+氯苯咕醇(pyridafol)、I+哒草特、I+环酯草醚、I+嘧草醚、I+嘧草醚甲酯、I+吡丙醚、I+嘧硫草醚、I+嘧硫草醚钠、I+罗克杀草砜、I+甲氧磺草胺、I+快杀稗、I+喹草酸、I+灭藻醌、I+喹禾灵、I+精喹禾灵、I+砜嘧磺隆、I+苯嘧磺草胺、I+稀禾定、I+环草隆、I+西玛津、I+西草净、I+氯酸钠、I+磺草酮、I+甲磺草胺、I+嘧磺隆、I+嘧磺隆甲酯、I+草硫膦(sulfosate)、I+磺酰磺隆、I+硫酸、I+丁噻隆、I+特呋三酮、I+环磺酮、I+吡喃草酮、I+特草定、I+甲氧去草净、I+特丁津、I+去草净、I+甲氧噻草胺、I+噻草啶、I+噻吩磺隆、I+噻酮磺隆(thiencarbazone)、I+噻吩磺隆甲酯、I+禾草丹、I+苯吡唑草酮、I+肟草酮、I+野麦畏、I+醚苯磺隆、I+三嗪氟草胺、I+苯磺隆、I+苯磺隆甲酯、I+绿草定、I+草达津、I+三氟啶磺隆、I+三氟啶磺隆钠、I+氟乐灵、I+氟胺磺隆、I+氟胺磺隆甲酯、I+三羟基三嗪、I+抗倒酯乙酯、I+三氟甲磺隆以及I+[3-[2-氯-4-氟-5-(1-甲基-6-三氟甲基-2,4-二氧代-1,2,3,4-四氢嘧啶-3-基)苯氧基]-2-吡啶基氧基]乙酸乙酯(CAS RN 353292-31-6)。本发明的具有化学式(I)的化合物和/或组合物还可以与在WO 06/024820和/或WO 07/096576中披露的除草化合物组合。
具有化学式(I)的化合物的混合配伍物还可以处于酯或盐的形式,如例如在杀有害生物剂手册(The Pesticide Manual),第十六版,英国作物保护委员会(British CropProtection Council),2012中所提到。
具有化学式(I)的化合物还可以在与其他农用化学品(例如杀真菌剂、杀线虫剂或杀昆虫剂)的混合物中使用,这些农用化学品的实例在杀有害生物剂手册(见上文)中给出)。
具有化学式(I)的化合物与混合配伍物的混合比优选地是从1:100至1000:1。
这些混合物可以有利地用于以上提到的这些配制品中(在这种情况下“活性成分”涉及具有化学式I的化合物与混合配伍物的对应混合物)。
如本文所描述的具有化学式(I)的化合物还可以与一种或多种安全剂组合使用。同样地,如本文所描述的具有化学式(I)的化合物与一种或多种另外的除草剂的混合物还可以与一种或多种安全剂组合使用。这些安全剂可以是AD 67(MON 4660)、解草嗪、解毒喹、环丙磺酰胺(CAS RN 221667-31-8)、二氯丙烯胺、解草唑乙酯、解草啶、氟草肟、解草噁唑和对应的R异构体、双苯噁唑酸乙酯、吡唑解草酸二乙酯、解草腈、N-异丙基-4-(2-甲氧基-苯甲酰基氨磺酰基)-苯甲酰胺(CAS RN 221668-34-4)。其他可能性包括例如在EP 0365484中披露的安全剂化合物,例如N-(2-甲氧基苯甲酰基)-4-[(甲基氨基羰基)氨基]苯磺酰胺。特别优选的是具有化学式I的化合物与环丙磺酰胺、双苯噁唑酸-乙基、解毒喹和/或N-(2-甲氧基苯甲酰基)-4-[(甲基-氨基羰基)氨基]苯磺酰胺的混合物。
该具有化学式(I)的化合物的这些安全剂还可以处于酯或盐的形式,如例如在杀有害生物剂手册(The Pesticide Manual)(见上文)中所提到。提及解毒喹还适用于锂、钠、钾、钙、镁、铝、铁、铵、季铵、锍或其鏻盐(如在WO 02/34048中披露的),并且对解草唑乙酯(fenchlorazole-ethyl)的提及还适用于解草唑(fenchlorazole),等等。
优选地,具有化学式(I)的化合物与安全剂的混合比是从100:1至1:10,尤其是从20:1至1:1。
这些混合物可有利地用于以上提到的这些配制品中(在这种情况下“活性成分”涉及具有化学式(I)的化合物与安全剂的对应混合物)。
如上所述,包括此类化合物的具有化学式(I)的化合物和/或组合物可以用于控制不想要的植物生长的方法中,和特别是用于在有用植物的作物中控制不想要的植物生长中。因此,本发明进一步提供了选择性地控制场所中的杂草的方法,该场所包括作物植物和杂草,其中该方法包括向该场所施用杂草控制量的如本文所描述的具有化学式(I)的化合物、或组合物。‘控制’意指杀死、减少或延迟生长或防止或减少发芽。通常有待控制的植物是不想要的植物(杂草)。‘场所’意指其中植物正生长或将生长的区域。
具有化学式(I)的化合物的施用率可以在宽范围之内变化并且取决于土壤的性质、施用方法(出苗前或出苗后;拌种;施用至种子垄沟;免耕施用等)、作物植物、有待控制的杂草、主要气候条件、以及受施用方法支配的其他因素、施用时间以及目标作物。根据本发明的具有化学式I的化合物通常以从10g/ha至2000g/ha,尤其是从50g/ha到1000g/ha的比率施用。
通常通过喷洒该组合物进行施用,典型地是通过用于大面积的装在拖拉机上的喷洒机,但是还可以使用其他方法如撒粉(针对粉末)、滴加或浸湿。
可以使用根据本发明的组合物的有用植物,包括作物如谷物,例如大麦和小麦、棉花、油菜籽油菜、向日葵、玉米、稻、大豆、甜菜、甘蔗以及草皮。
作物植物还可以包括树,如果树、棕榈树、椰子树或其他坚果。还包括藤本植物(如葡萄)、灌木果树、果实植物和蔬菜。
作物应被理解为还包括通过常规的育种方法或通过基因工程已经赋予对除草剂或多种类别的除草剂(例如ALS-抑制剂、GS-抑制剂、EPSPS-抑制剂、PPO-抑制剂、ACC酶-抑制剂以及HPPD-抑制剂)的耐受性的那些作物。通过常规的育种方法已经赋予其对咪唑啉酮(例如,甲氧咪草烟)的耐受性的作物的实例是夏季油菜(卡罗拉(canola))。通过基因工程方法而赋予对除草剂的耐受性的作物的实例包括例如草甘膦和草丁膦抗性的玉米品种,这些玉米品种在和商标名下是可商购的。在具体优选方面,该作物植物已经如在例如WO 2010/029311中所传授的被工程化,以过表达尿黑酸茄呢基转移酶。
农作物还应理解为通过基因工程方法已经赋予其对有害昆虫有抗性的那些农作物,例如Bt玉米(对欧洲玉米螟有抗性)、Bt棉花(对棉铃象鼻虫有抗性)以及还有Bt马铃薯(对科罗拉多甲虫有抗性)Bt玉米的实例是的Bt 176玉米杂交体(先正达种子公司(Syngenta Seeds))。Bt毒素是由苏芸金芽孢杆菌土壤细菌天然形成的蛋白质。毒素或能够合成此类毒素的转基因植物的实例描述于EP-A-451 878、EP-A-374 753、WO 93/07278、WO95/34656、WO 03/052073以及EP-A-427 529中。包括一个或多个编码杀昆虫剂抗性和表达一种或多种毒素的基因的转基因植物的实例是(玉米)、Yield(玉米)、(棉花)、(棉花)、(马铃薯)、以及其植物作物或种子材料均可以是抗除草剂的并且同时是抗昆虫摄食的(“叠加的”转基因结果)。例如,种子可以在具有表达杀虫的Cry3蛋白的能力的同时是耐草甘膦的。
作物还应被理解为包括通过常规的育种或基因工程的方法获得并且包含所谓的输出性状(例如改进的储存稳定性、更高的营养价值以及改进的香味)的那些。
其他有用的植物包括例如在高尔夫球场、草地、公园以及路旁的或者商业上种植用于草地的草皮草,以及观赏植物,如花卉或者灌木。
可以使用这些组合物来控制不想要的植物(统称为‘杂草’)。待控制的杂草包括单子叶(例如禾本科)的物种(例如剪股颖属(Agrostis)、看麦娘属(Alopecurus)、燕麦属(Avena)、臂形草属(Brachiaria)、雀麦属(Bromus)、蒺藜草属(Cenchrus)、莎草属(Cyperus)、马唐属(Digitaria)、稗属(Echinochloa)、穇属(Eleusine)、黑麦草属(Lolium)、雨久花属(Monochoria)、筒轴茅属(Rottboellia)、慈姑属(Sagittaria)、藨草属(Scirpus)、狗尾草属(Setaria)以及高粱属(Sorghum));和双子叶的物种(例如苘麻属(Abutilon)、苋属(Amaranthus)、豚草属(Ambrosia)、藜属(Chenopodium)、菊属(Chrysanthemum)、白酒草属(Conyza)、拉拉藤属(Galium)、番薯属(Ipomoea)、地肤属(Kochia)、旱金莲属(Nasturtium)、蓼属(Polygonum)、黄花稔属(Sida)、白芥属(Sinapis)、茄属(Solanum)、繁缕属(Stellaria)、婆婆纳属(Veronica)、堇菜属(Viola)以及苍耳属(Xanthium))。杂草还可以包括可被认为是作物植物但是在作物区外生长的植物(‘逃逸者(escapes)’),或从先前栽培的不同作物留下的种子生长的植物(‘志愿者(volunteers)’)。此类志愿者或逃逸者可以是对某些其他除草剂耐受的。
优选地,待控制和/或生长抑制的杂草包括单子叶杂草、更优选地禾本科单子叶杂草、特别的来自以下属的那些:剪股颖属(Agrostis)、看麦娘属(Alopecurus)、阿披拉草属(Apera)、燕麦属(Avena)、臂形草属(Brachiaria)、雀麦属(Bromus)、蒺藜草属(Cenchrus)、莎草属(Cyperus)(莎草科(sedge)的属)、马唐属(Digitaria)、稗属(Echinochloa)、椮属(Eleusine)、野黍属(Eriochloa)、飘拂草属(Fimbristylis)(莎草科的属)、灯心草属(Juncus)(灯心草科(rush)的属)、千金子属(Leptochloa)、黑麦草属(Lolium)、鸭舌草属(Monochoria)、露籽草属(Ottochloa)、黍属(Panicum)、狼尾草属(Pennisetum)、虉草属(Phalaris)、早熟禾属(Poa)、筒轴草属(Rottboellia)、慈菇属(Sagittarta)、藨草属(Scirpus)(莎草科的属)、狗尾草属(Setaria)和/或高粱属(Sorghum),和/或自生自长的玉米(自生自长的玉蜀黍)杂草;具体地:大穗看麦娘(Alopecurus myosuroides)(ALOMY,英文名“黑草”)、阿披拉草(Apera spica-venti)、野燕麦(Avena fatua)(AVEFA,英文名“野生燕麦”)、长颖燕麦(Avena ludoviciana)、不实燕麦(Avena sterilis)、燕麦(Avena sativa)(英文名“燕麦(oats)”(自生植物))、伏生臂形草(Brachiaria decumbens)、车前臂形草(Brachiaria plantaginea)、宽叶臂形草(Brachiaria platyphylla)(BRAPP)、旱雀麦(Bromus tectorum)、水平尾马唐(Digitaria horizontalis)、两耳马唐(Digitariainsularis)、马唐(Digitaria sanguinalis)(DIGSA)、稗草(Echinochloa crus-galli)(英文名“常见稗草”,ECHCG)、水田稗(Echinochloa oryzoides)、光头稗(Echinochloa colona或colonum)、牛筋草(Eleusine indica)、野黍(Eriochloa villosa)(英文名“乌利千草杯”)、千金子(Leptochloa chinensis)、亚马逊千金子(Leptochloa panicoides)、多年生黑麦草(Lolium perenne)(LOLPE,英文名“多年生的黑麦草”)、多花黑麦草(Loliummultiflorum)(LOLMU,英文名“意大利黑麦草”)、欧黑麦草(Lolium persicum)(英文名“波斯黑麦草”)、硬直黑麦草(Lolium rigidum)、洋野黍(Panicum dichotomiflorum)(PANDI)、黍稷(Panicum miliaceum)(英文名“野生黍稷”)、小子虉草(Phalaris minor)、奇异虉草(Phalaris paradoxa)、早熟禾(Poa annua)(POAAN,英文名“一年生早熟禾”)、滨海藨草(Scirpus maritimus)、萤蔺(Scirpus juncoides)、翠绿狗尾草(Setaria viridis)(SETVI,英文名“绿狗尾草”)、大狗尾草(Setaria faberi)(SETFA,英文名“大狗尾草(giantfoxtail)”)、狗尾草(Setaria glauca)、金狗尾草(Setaria lutescens)(英文名“金黄狗尾草”)、两色蜀黍(Sorghum bicolor)、和/或假高粱(Sorghum halapense)(英文名“约翰逊草”)、和/或高粱(Sorghum vulgare);和/或自生自长的玉米(自生自长的玉蜀黍)杂草。
在一个实施例中,待控制的禾草科单子叶杂草包括来自以下各属的杂草:剪股颖属(Agrostis)、看麦娘属(Alopecurus)、阿披拉草属(Apera)、燕麦属(Avena)、臂形草属(Brachiaria)、雀麦属(Bromus)、蒺藜草属(Cenchrus)、马唐属(Digitaria)、稗属(Echinochloa)、椮属(Eleusine)、野黍属(Eriochloa)、千金子属(Leptochloa)、黑麦草属(Lolium)、露籽草属(Ottochloa)、黍属(Panicum)、狼尾草属(Pennisetum)、虉草属(Phalaris)、早熟禾属(Poa)、筒轴草属(Rottboellia)、狗尾草属(Setaria)和/或高粱属(Sorghum)、和/或自生自长的玉米(自生自长的玉蜀黍)杂草;特别地:来自以下各属的杂草:剪股颖属(Agrostis)、看麦娘属(Alopecurus)、阿披拉草属(Apera)、燕麦属(Avena)、臂形草属(Brachiaria)、雀麦属(Bromus)、蒺藜草属(Cenchrus)、马唐属(Digitaria)、稗属(Echinochloa)、椮属(Eleusine)、野黍属(Eriochloa)、千金子属(Leptochloa)、黑麦草属(Lolium)、黍属(Panicum)、虉草属(Phalaris)、早熟禾属(Poa)、筒轴草属(Rottboellia)、狗尾草属(Setaria)、和/或高粱属(Sorghum)、和/或自生自长的玉米(自生自长的玉蜀黍)杂草。
在另外的实施例中,禾草科单子叶杂草是“暖季型”(温暖气候型)禾本科杂草;在这种情况下,它们优选地包括(例如是):来自以下各属的杂草:臂形草属(Brachiaria)、蒺藜草属(Cenchrus)、马唐属(Digitaria)、稗属(Echinochloa)、椮属(Eleusine)、野黍属(Eriochloa)、千金子属(Leptochloa)、露籽草属(Ottochloa)、黍属(Panicum)、狼尾草属(Pennisetum)、虉草属(Phalaris)、筒轴草属(Rottboellia)、狗尾草属(Setaria)和/或高粱属(Sorghum)、和/或自生自长的玉米(自生自长的玉蜀黍)杂草。更优选地,例如待控制和/或生长抑制的禾草科单子叶杂草是“暖季型”(温暖气候)禾草科杂草,其包括(例如是)来自以下各属的杂草:臂形草属(Brachiaria)、蒺藜草属(Cenchrus)、马唐属(Digitaria)、稗属(Echinochloa)、椮属(Eleusine)、野黍属(Eriochloa)、黍属(Panicum)、狗尾草属(Setaria)和/或高粱属(Sorghum)、和/或自生自长的玉米(自生自长的玉蜀黍)杂草。
在另一个具体实施例中,禾本科单子叶杂草是“冷季”(凉爽气候)禾本科杂草;在该情况下它们典型地包括来自以下各属的杂草:剪股颖属、看麦娘属、阿披拉草属、燕麦属、雀麦属、黑麦草属和/或早熟禾属。
现在通过举例更详细地说明本发明的不同方面和实施例。应当理解的是,在不偏离本发明范围的情况下,可以对细节做出修改。
制备实例
贯穿以下实例,在Varian Unity Inova仪器上或者在Bruker AVANCE-II仪器上在400Mhz或500MHz下记录1H NMR光谱。
使用了以下缩写:s=单峰;bs=宽单峰;d=二重峰;bd=宽二重峰;dd=双二重峰;t=三重峰;q=四重峰;m=多重峰;THF=四氢呋喃;EtOAc=乙酸乙酯;EtOH=乙醇;DMSO=二甲基亚砜;DPPA=叠氮磷酸二苯酯;DMF=N,N-二甲基甲酰胺;dppf=1,1′-双(联苯膦基)二茂铁;Pd(OAc)2=乙酸钯(II);Et3N=三乙胺;MeOH=甲醇。
使用Accelrys Draw 4.0中的‘Text from structure’功能生成化学名称。
实例P1 化合物A2,叔-丁基N-[2-甲基-5-(3-吡啶基)吡唑-3-基]氨基甲酸酯的制备
1.1步骤1:2,4-二氧代-4-(3-吡啶基)丁酸乙酯的制备
将NaH(60%w/w,9.91g,248.0mmol)添加到装有无水THF(170mL)的烧瓶中。添加草酸二乙酯(24.13g,165.1mmol),并用无水THF(15mL)洗涤。将该混合物加热至回流,然后在回流下伴随搅拌缓慢添加1-(3-吡啶基)乙酮(10.0g,82.55mmol)在THF(15mL)中的溶液。15分钟后,将该混合物冷却至室温,并在搅拌和冷却下缓慢添加到在水(375mL)中的2M HCl(130mL)的混合物中。将所得混合物用固体NaHCO3处理直到轻微碱性,然后用EtOAc萃取三次。将合并的有机物用盐水洗涤一次,干燥(MgSO4)并真空浓缩,得到深棕色胶状物,令其静置固化。
通过洗涤和用己烷倾析除去矿物油。将固体溶于温热乙醇(350mL)中并用脱色木炭处理。5分钟后,将该溶液通过硅藻土热过滤。将滤液真空浓缩,得到粗的2,4-二氧代-4-(3-吡啶基)丁酸乙酯(15.0g),其不经进一步纯化即可使用。
1H NMR(400MHz,CDCl3)δ=9.21(1H,d),8.83(1H,dd),8.29(1H,m),7.46-7.52(1H,m),7.08(1H,s),4.39-4.46(2H,q),1.40-1.46(3H,t)。
1.2步骤2:2-甲基-5-(3-吡啶基)吡唑-3-甲酸乙酯的制备
向填充溶解于EtOH(120mL)中的2,4-二氧代-4-(3-吡啶基)丁酸乙酯(10.0g,45.2mmol)的烧瓶中添加甲基肼(2.4mL,46.0mmol)。将混合物加热至回流,持续2.5小时,然后静置过夜。
真空除去溶剂,并使用EtOAc/己烷梯度,将粗材料经由硅胶快速柱色谱法纯化,以得到乙基2-甲基-5-(3-吡啶基)吡唑-3-甲酸酯(2.52g)。
1H NMR(400MHz,CDCl3)δ=9.02(1H,m),8.56(1H,dd),8.11(1H,m),7.34(1H,dd),7.17(1H,s),4.39(2H,q),4.25(3H,s),1.42(3H,t)
1.3步骤3:2-甲基-5-(3-吡啶基)吡唑-3-甲酸乙基酯的制备
向冷却于冰浴中、装有溶解于1,4-二噁烷(17mL)中的2-甲基-5-(3-吡啶基)吡唑-3-甲酸乙基酯(2.52g,10.9mmol)的烧瓶中滴加在水(3.3mL)中的NaOH(1.09g,27.3mmol)。将所得的双相溶液在环境温度下搅拌2小时,然后分批添加水直至均匀(13.2mL)。
将反应混合物在环境温度下再搅拌2小时,此后将溶剂真空浓缩至约50%体积,并用水(20mL)稀释。将反应混合物用2M HCl(13.5mL)酸化,并将固体沉淀物在泵上过滤,用水洗涤并空气干燥过夜,以得到呈灰白色固体的2-甲基-5-(3-吡啶基)吡唑-3-甲酸(1.70g)。
1H NMR(400MHz,d6-DMSO)δ=9.06(1H,m),8.53(1H,dd),8.20(1H,d),7.45(1H,m),7.43(1H,s),4.15(3H,s)。
1.4步骤4:N-[2-甲基-5-(3-吡啶基)吡唑-3-基]氨基甲酸叔丁基酯的制备
伴随搅拌,向装有悬浮于叔丁醇(37mL)和甲苯(37mL)中的2-甲基-5-(3-吡啶基)吡唑-3-甲酸(1.70g,8.34mmol)的烧瓶中滴加三乙胺(1.18mL,8.38mmol)和DPPA(2.30g,8.40mmol),并然后将所得混合物逐渐加热至回流。回流4.5小时后,使反应混合物冷却,并真空除去溶剂。使用EtOAc/己烷梯度,将残余物经由硅胶快速柱色谱法纯化,以得到呈无色胶状的N-[2-甲基-5-(3-吡啶基)吡唑-3-基]氨基甲酸叔丁基酯(0.75g)。
1H NMR(400MHz,CDCl3)δ=8.98(1H,bs),8.53(1H,bs),8.05(1H,m),7.30(1H,m),6.63(1H,bs),6.53(1H,bs),3.81(3H,s),1.53(9H,s)。
实例P2 化合物A1,N-甲基-N-[2-甲基-5-(3-吡啶基)吡唑-3-基]氨基甲酸叔丁基酯的制备
将N-[2-甲基-5-(3-吡啶基)吡唑-3-基]氨基甲酸叔丁基酯(245mg,0.893mmol)溶于无水DMF(2.5mL)中,在冰浴中冷却,然后以单一部分添加NaH(60%w/w,42.9mg,1.07mmol)。5分钟后,允许混合物温热至环境温度5分钟(溶液变成棕色)。重新应用冰浴,并滴加无水DMF(0.7mL)中的MeI(133.1mg,0.938mmol)溶液。30分钟后,将反应升温至环境温度并再搅拌1小时。
用含有2M Hcl(89μL)的水(13mL)淬灭反应。将该混合物用EtOAc萃取3次,并且将合并的有机物用盐水洗涤2次,并且然后干燥(MgSO4)。真空浓缩溶剂并使用EtOAc/己烷梯度,将残余物经由硅胶快速柱色谱法纯化,以得到呈琥珀色胶状的N-甲基-N-[2-甲基-5-(3-吡啶基)吡唑-3-基]氨基甲酸叔丁基酯(125.0mg)。
1H NMR(400MHz,CDCl3)δ=8.97(1H,d),8.51-8.56(1H,m)8.07(1H,d),7.28-7.35(1H,m),6.40(1H,s),3.75(3H,s),3.22(3H,s),1.45(9H,s)。
实例P3 化合物A3,N-(3-甲基-1-嘧啶-5-基-吡唑-4-基)氨基甲酸叔丁基酯的制备
3.1步骤1:3-甲基-1-嘧啶-5-基-吡唑-4-甲酸乙酯的制备
向装有溶解于1,4-二噁烷(5mL)中的5-溴嘧啶(248mg,1.56mmol)的烧瓶中添加K2CO3(359mg,2.59mmol)、CuI(124mg,0.065mmol)、反式-N,N'-二甲基环己烷-1,2-二胺(28.5mg,0.195mmol)和3-甲基-1H-吡唑-4-甲酸乙酯(200mg,1.30mmol)。这得到蓝色悬浮液,将其加热至110℃并搅拌过夜。
一夜之间,该反应已经变成了深灰色。冷却后,将反应混合物倒入EtOAc和水中。将其用EtOAc萃取两次。将合并的有机物用盐水洗涤并干燥(MgSO4),将合并的有机物真空浓缩,得到棕色固体,将该棕色固体经由硅胶快速柱色谱法使用EtOAc/己烷梯度纯化,以得到呈白色固体的3-甲基-1-嘧啶-5-基-吡唑-4-甲酸乙酯(255mg)。
1H NMR(400MHz,CDCl3)δ=9.18(1H,s),9.14(2H,s),8.42(1H,s),4.35(2H,q),2.58(3H,s),1.39(3H,t)。
3.2步骤2:3-甲基-1-嘧啶-5-基-吡唑-4-甲酸的制备
向装有在1,4-二噁烷(3.4mL)中的3-甲基-1-嘧啶-5-基-吡唑-4-甲酸乙酯(180mg,0.775mmol)的烧瓶中添加溶解于水(1.7mL)中的NaOH(68.2mg 1.71mmol),以形成淡黄色溶液,将所得溶液在55℃搅拌过夜。
将反应混合物真空浓缩以除去有机物,并将水层用1M HCl酸化至pH 3,得到白色固体。在泵上滤出沉淀物并用水洗涤两次,然后用EtOAc洗涤并空气干燥,得到呈白色固体的3-甲基-1-嘧啶-5-基-吡唑-4-甲酸(84mg)。
1H NMR(400MHz,d6-DMSO)δ=9.35(2H,s),9.15(1H,s),9.10(1H,s),2.42(3H,s)。
3.3步骤3:N-(3-甲基-1-嘧啶-5-基-吡唑-4-基)氨基甲酸叔丁基酯,化合物A3的制备
向装有3-甲基-1-嘧啶-5-基-吡唑-4-甲酸(0.206g,1.01mmol)和叔丁醇(7mL)的烧瓶中通过注射器滴加三乙胺(0.141mL,1.0mmol)。向其中通过注射器滴加DPPA(0.219mL,1.01mmol),并将混合物加热至回流过夜。
过夜形成白色沉淀,并且冷却后,将其在泵中过滤出,并真空浓缩滤液,留下黄色残余物。将其在水和EtOAc之间分配。用另外3部分EtOAc萃取水层。将合并的有机物用盐水洗涤,干燥(MgSO4),并蒸发至干,得到膏状固体(297mg)。将该粗产物通过硅胶快速柱层析法用EtOAc/异己烷梯度洗脱进行纯化,以给出呈白色固体(64mg)的N-(3-甲基-1-嘧啶-5-基-吡唑-4-基)氨基甲酸叔丁基酯。
1H NMR(400MHz,CDCl3)δ=9.08(3H,s),8.28(1H,s),6.17(1H,s),2.31(3H,s),1.54(9H,s)。
实例P4 N-甲基-N-(3-甲基-1-嘧啶-5-基-吡唑-4-基)氨基甲酸叔丁基酯,化合物A5的制备
在氮气下,向装有溶解于DMF(1mL)中并于冰浴中冷却的N-(3-甲基-1-嘧啶-5-基-吡唑-4-基)氨基甲酸叔丁基酯(68.0mg,0.25mmol)的烧瓶中以单一部分添加NaH(60%w/w11.0mg,0.27mmol),得到亮黄色溶液。将混合物在冰浴中搅拌10分钟,然后温热至环境温度持续40分钟。重新应用冰浴,并通过注射器滴加MeI(16μL,0.26mmol)。将反应在环境温度下搅拌2小时,并用水淬灭和用Et2O萃取两次。将合并的有机物用盐水洗涤,干燥(MgSO4),并真空浓缩,得到呈白色固体的N-甲基-N-(3-甲基-1-嘧啶-5-基-吡唑-4-基)氨基甲酸叔丁基酯(51mg)。
1H NMR(400MHz,CDCl3)δ=9.10(1H,s),9.06(2H,s),7.85(1H,s),3.21(3H,s),2.28(3H,s),1.57(9H,s)。
实例P5 异丙基N-[2-(二氟甲基)-5-嘧啶-5-基-吡唑-3-基]氨基甲酸酯,化合物A58的制备
步骤一:嘧啶-5-甲酸甲酯的合成
将一氧化碳气体引入在MeOH(120mL)中的5-溴嘧啶(15.9g,0.1mol)、dppf(2.22g,4mmol)、Pd(OAc)2(448mg,2mmol)和Et3N(20.2g,0.2mol)的混合物中并将内压增加至30巴。将反应混合物在95℃下搅拌约4小时,然后冷却至室温并过滤。减压浓缩滤液,并将残余物通过硅胶柱色谱纯化(洗脱剂:石油醚/乙酸乙酯=5:1),得到呈白色固体的嘧啶-5-甲酸甲酯(9.6g,70%收率)。
1H NMR(400MHz,CDCl3)δ=9.36(1H,s),9.27(2H,s),3.98(3H,s)。
步骤二:3-嘧啶-5-基-1H-吡唑-5-胺的合成
将嘧啶-5-甲酸甲酯(5.3g,38mmol)添加到在乙腈(1.57g,38mmol)和THF(50mL)中的NaH(2.4g,60mmol)的悬浮液中,并将混合物在回流下加热过夜。滤出沉淀,并用二乙醚洗涤,得到呈黄色固体的3-氧代-3-嘧啶-5-基-丙腈钠盐,其不经进一步纯化直接用于下一步骤。
将在EtOH(100mL)中的3-氧代-3-嘧啶-5-基-丙腈钠盐(5g)、肼盐酸盐(3.0g,44mmol)、乙酸(1.7g,30mmol)和盐酸(0.2mL,1M)的混合物在回流下加热3小时。然后将反应混合物冷却至室温并真空浓缩。将残余物通过硅胶柱色谱纯化,得到呈黄色固体的5-嘧啶-5-基-1H-吡唑-3-胺(1.5g)。
1H NMR(400MHz,DMSO-d6)δ=11.84(1H,bs),9.03(3H,s),5.85(1H,s),5.09(2H,bs)。
步骤三:2-(二氟甲基)-5-嘧啶-5-基-吡唑-3-胺的合成
在高压釜中,将CHClF2(26.66g,310mmol)引入在二噁烷(30mL)和水(20mL)中的5-嘧啶-5-基-1H-吡唑-3-胺(5g,31mmol)和KOH(8.68g,155mmol)的混合物中。将反应混合物在100℃加热,并将内压增加至15巴。搅拌4h后,将反应混合物冷却至室温,用水(50mL)稀释并用EtOAc萃取3次。将合并的萃取液用无水硫酸钠干燥,真空浓缩并通过硅胶快速色谱纯化(洗脱剂石油醚/乙酸乙酯3:1),得到呈黄色固体的1-(二氟甲基)-5-嘧啶-5-基-吡唑-3-胺(260mg)和想要的2-(二氟甲基)-5-嘧啶-5-基-吡唑-3-胺(260mg)。
1H NMR(400MHz,DMSO-d6)δ=9.17(1H,s),9.14(2H,s),7.65(1H,t),6.19(2H,s),5.97(1H,s)。
步骤四:N-[2-(二氟甲基)-5-嘧啶-5-基-吡唑-3-基]氨基甲酸异丙基酯,化合物A58的合成
向装有2-(二氟甲基)-5-嘧啶-5-基-吡唑-3-胺(100mg,0.47mmol)的小瓶中添加二氯甲烷(7mL)与吡啶(94mg,1.184mmol)并将该混合物搅拌5分钟。滴加氯甲酸异丙酯(1M,在甲苯中)(0.59mmol,0.59mL),并将混合物搅拌过夜。将样品真空浓缩并预先吸附到硅胶上,然后使用EtOAc/己烷梯度通过快速柱色谱纯化,得到呈稠胶状物的所希望的产物(82mg)。
1H NMR(400MHz,CDCl3)δ=9.22(1H,s),9.16(2H,s),7.28(1H,t),7.20(1H,bs),6.92(1H,bs),5.05(1H,m),1.30(6H,d)。
实例P6 N-[2-(二氟甲基)-5-嘧啶-5-基-吡唑-3-基]-N-甲基-氨基甲酸异丙基酯,化合物A59的制备
向装有异丙基N-[2-(二氟甲基)-5-嘧啶-5-基-吡唑-3-基]氨基甲酸酯(82mg,0.276mmol)的烧瓶中添加DMF(5mL)并搅拌至均匀。将混合物冷却至0℃(冰浴),并以单一部分添加氢化钠(65%w/w,在矿物油中)(12mg,0.29mmol)。5分钟后,将混合物从冰浴中取出并在环境温度下再搅拌5分钟。然后将烧瓶重新冷却至0℃(冰浴),并滴加碘甲烷(42mg,0.295mmol,0.0180mL)。10分钟后,允许混合物温热至环境温度并再搅拌30分钟。将混合物用2M HCl(500μL)淬灭并真空浓缩。然后将所得残余物溶解在CH2Cl2中并预先吸附到硅胶上,然后使用EtOAc/己烷梯度在硅胶上通过快速柱色谱纯化。此步骤得到呈白色固体的所需化合物(44mg)。
1H NMR(400MHz,CDCl3)δ=9.22(1H,s),9.12(2H,s),7.14(1H,t),6.60(1H,s),4.98(1H,m),3.27(3H,s),1.22(6H,bd)。
实例P7 N-[3-氯-1-(3-吡啶基)吡唑-4-基]-N-甲基-氨基甲酸叔丁基酯,化合物A60的制备
N-[3-氯-1-(3-吡啶基)吡唑-4-基]氨基甲酸叔丁基酯是根据US8901153中的程序制备的。
经约5分钟,向装有在DMF(6mL)中并在冰浴中冷却的N-[3-氯-1-(3-吡啶基)吡唑-4-基]氨基甲酸叔丁基酯(200mg,0.69mmol)的烧瓶中滴加氢化钠(60%w/w,在油中)(30mg,0.75mmol)。在这段时间反应混合物变成深黄色,并且可观察到细小的沉淀。然后将混合物温热至室温并搅拌5分钟。重新应用冰浴,并滴加碘甲烷(212mg,1.49mmol,92μL)。将混合物在冰浴中搅拌2小时,然后温热至环境温度,并用盐水(5mL)稀释。将反应用EtOAc(3×10mL)萃取,并将合并的有机物真空浓缩,并且然后装载到SiO2柱上,然后通过硅胶快速柱色谱(用EtOAc/己烷梯度洗脱)纯化,得到呈无色油状物的所需化合物(102mg)。
1H NMR(400MHz,CDCl3)δ=8.92(1H,d),8.57(1H,d),8.07(1H,m),7.90(1H,bs),7.42(1H,m),3.22(3H,s),1.39(9H,s)。
使用上述实例P1至P7中关于化合物A1、A2、A3、A5、A58、A59和A60的方法,以类似的方式制备本发明的其他实例。下表2总结了这些化合物的物理数据。
表2:通过上述方法制备的化合物
生物学实例
B1出苗前除草活性
将多种测试物种的种子播种在盆中的标准土壤中。普通小麦(TRZAW)、水稻(ORYSA)、野燕麦(AVEFA)、大穗看麦娘(Alopecurus myosuroides)(ALOMY)、稗草(ECHCG)、黑麦草(LOLPE)。在温室(在24℃/16℃白天/夜晚下;14小时光照;65%湿度)中在受控条件下培养一天之后(出苗前),用水性喷雾溶液喷洒这些植物,该水性喷雾溶液源自工业级活性成分在丙酮/水(50:50)溶液中的配制品,该溶液含有0.5%吐温20(聚氧乙烯脱水山梨糖醇单月桂酸酯,CAS RN 9005-64-5)。然后使测试植物在受控制的条件(在24℃/16℃日/夜下;14小时光照;65%湿度)下生长于温室中,并且每天浇水两次。13天之后,对测试进行评估(5=对植物完全性的损害;0=对植物没有损害)。结果示于下面的表3中。
表3通过出苗前施用具有化学式(I)的化合物对杂草物种的控制
B1a出苗前除草活性
将多种测试物种的种子播种在盆中的标准土壤中。反枝苋(AMARE)、大狗尾草(SETFA)、玉米(ZEAMX)、茼麻(Abutilon threophrasti)(ABUTH)、稗草(ECHCG)、黑麦草(LOLPE)。在温室(在24℃/16℃白天/夜晚下;14小时光照;65%湿度)中在受控条件下培养一天之后(出苗前),用水性喷雾溶液喷洒这些植物,该水性喷雾溶液源自工业级活性成分在丙酮/水(50:50)溶液中的配制品,该溶液含有0.5%吐温20(聚氧乙烯脱水山梨糖醇单月桂酸酯,CAS RN 9005-64-5)。然后使测试植物在受控制的条件(在24℃/16℃日/夜下;14小时光照;65%湿度)下生长于温室中,并且每天浇水两次。13天之后,对测试进行评估(5=对植物完全性的损害;0=对植物没有损害)。结果示于下面的表4中
表4通过出苗前施用具有化学式(I)的化合物对杂草物种的控制
B2出苗后除草活性
将多种测试物种的种子播种在盆中的标准土壤中。普通小麦(TRZAW)、水稻(ORYSA)、野燕麦(AVEFA)、大穗看麦娘(Alopecurus myosuroides)(ALOMY)、稗草(ECHCG)、黑麦草(LOLPE)。在温室(在24℃/16℃白天/夜晚下;14小时光照;65%湿度)中在受控条件下栽培(出苗前)八天后,用水性喷雾溶液喷洒这些植物,该水性喷雾溶液源自工业级活性成分在丙酮/水(50:50)溶液中的配制品,该溶液含有0.5%吐温20(聚氧乙烯脱水山梨糖醇单月桂酸酯,CAS RN 9005-64-5)。然后使测试植物在受控制的条件(在24℃/16℃日/夜下;14小时光照;65%湿度)下生长于温室中,并且每天浇水两次。13天之后,对测试进行评估(5=对植物完全性的损害;0=对植物没有损害)。结果在下表5中示出。
表5通过出苗后施用具有化学式(I)的化合物对杂草物种的控制
B2a出苗后除草活性
将多种测试物种的种子播种在盆中的标准土壤中。反枝苋(AMARE)、大狗尾草(SETFA)、玉米(ZEAMX)、茼麻(ABUTH)、稗草(ECHCG)、黑麦草(LOLPE)。在温室(在24℃/16℃白天/夜晚下;14小时光照;65%湿度)中在受控条件下栽培(出苗前)八天后,用水性喷雾溶液喷洒这些植物,该水性喷雾溶液源自工业级活性成分在丙酮/水(50:50)溶液中的配制品,该溶液含有0.5%吐温20(聚氧乙烯脱水山梨糖醇单月桂酸酯,CAS RN 9005-64-5)。然后使测试植物在受控制的条件(在24℃/16℃日/夜下;14小时光照;65%湿度)下生长于温室中,并且每天浇水两次。13天之后,对测试进行评估(5=对植物完全性的损害;0=对植物没有损害)。结果在下表6中示出。
表6通过出苗后施用具有化学式(I)的化合物对杂草物种的控制
Claims (25)
1.一种具有化学式(I)的化合物,
或其盐或N-氧化物作为除草剂的用途,其中Q是选自
或的环系统,
其中A表示与杂芳基环的附接点,以及B表示与氮原子的附接点;
X1是N或CR1;
R1是氢、卤素、氰基、C1-C6烷基、C3-C6环烷基、C2-C6烯基、C2-C6炔基、C1-C6烷氧基、C(=O)OR6或S(=O)n(C1-C6烷基)、甲酰基、羟基、-(=O)CNR6R7、NR6R7、苄氧基、C1-C6卤代烷氧基或C1-C6卤代烷基;
R2是氢、卤素、氰基、硝基、C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、C(=O)OR6、或S(=O)n(C1-C6烷基)、C1-C6烷氧基、C1-C6卤代烷氧基;
n是0、1、或2;
R3是氢、氰基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C2-C6卤代烯基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6卤代烷氧基、C2-C6烯氧基、C3-C10环烷基、NR6R7;
R4是O、S、或N(C1-C6烷基);
X2是O、S、或NR8;
R5是氢,C1-C6烷基,C2-C6烯基,C2-C6炔基,C3-C10环烷基,C3-C10环烯基,C1-C6卤代烷基,C2-C6卤代烯基,C1-C6烷氧基,C1-C6卤代烷氧基,C2-C6烯氧基,C2-C6炔氧基,C3-C10环烷氧基,C3-C10环烯氧基,C2-C6卤代烯氧基,C6-C10芳基或被从1至3个独立地选自卤素、硝基、氰基、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基和C1-C3卤代烷氧基的基团取代的C6-C10芳基;C3-C10杂环基或被从1至3个独立地选自卤素、硝基、氰基、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基、和C1-C3卤代烷氧基的基团取代的C3-C10杂环基;或NR6R7;
或R3和R5连同X2以及它们所连接的原子一起形成饱和或部分不饱和5-9元环系统,该5-9元环系统任选地包括1至3个独立地选自S、O和N的杂原子并且任选地被1至3个独立地选自卤素或C1-C6烷基的基团取代;
或R3和R8连同它们所连接的原子一起形成饱和或部分不饱和5-9元环系统,该5-9元环系统任选地包括1至3个独立地选自S、O和N的杂原子并且任选地被1至3个独立地选自卤素或C1-C6烷基的基团取代;
R6和R7各自独立地是氢、C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、或C2-C6炔基,
或R6和R7连同它们所连接的氮原子一起形成饱和或部分不饱和3-6元环,该3-6元环任选地包括1至3个独立地选自S、O和N的杂原子并且任选地被1至3个独立地选自卤素或C1-C6烷基的基团取代;
R8是氢、氰基、C1-C6烷基、C1-C6卤代烷基、C2-C6烯基或C2-C6炔基;C1-C6烷氧基、C1-C6卤代烷氧基、C2-C6烯氧基、C2-C6炔氧基、C3-C10环烷基氧基、C3-C10环烯氧基、C2-C6卤代烯氧基;
或R7和R8连同它们所连接的碳原子一起形成饱和或部分不饱和3-9元环,该3-9元环任选地包括1至3个独立地选自S、O和N的杂原子并且任选地被1至3个独立地选自卤素或C1-C6烷基的基团取代,
R9是氢、卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、C2-C6炔基、C1-C6卤代烷氧基、C1-C6烷氧基、或C3-C6环烷基;
R10是氢、C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6烷基硫基、-C(O)OR6、C1-C6烷氧基、C1-C6卤代烷氧基、C3-C6环烷基、或C2-C6炔基。
2.根据权利要求1所述的具有化学式(I)的化合物的用途,其中R1是氢、卤素、甲酰基、氰基、C1-C6烷氧基、C1-C6烷基磺酰基、C1-C6烷基硫基、C1-C6卤代烷氧基、-(O)CNR6R7、NR6R7、或C1-C6卤代烷基。
3.根据权利要求1或权利要求2所述的具有化学式(I)的化合物的用途,其中R1是氢、氟、氯、氰基、三氟甲基、甲氧基、二氟甲氧基、甲酰基、甲烷磺酰基、甲酰胺、甲硫醇或氨基。
4.根据权利要求1至3中任一项所述的具有化学式(I)的化合物的用途,其中R2是卤素、氰基、硝基、C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6烷基硫基、-C(O)OR6、C1-C6烷氧基、C1-C6卤代烷氧基、C3-C6环烷基、或C2-C6炔基。
5.根据前述权利要求中任一项所述的具有化学式(I)的化合物的用途,其中R2是卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、C1-C6烷氧基、C1-C6卤代烷氧基、C3-C6环烷基、-C(=O)OR6、或C2-C6炔基。
6.根据前述权利要求中任一项所述的具有化学式(I)的化合物的用途,其中R2是甲基、三氟甲基、氯、溴、碘、氟、乙烯基、乙炔基、甲氧基羰基、-CO2H或环丙基。
7.根据前述权利要求中任一项所述的具有化学式(I)的化合物的用途,其中R3是氢或C1-C3烷基。
8.根据前述权利要求中任一项所述的具有化学式(I)的化合物的用途,其中R3是氢或甲基。
9.根据前述权利要求中任一项所述的具有化学式(I)的化合物的用途,其中R5是C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C10环烷基、C1-C6卤代烷基、C2-C6卤代烯基、C1-C6烷氧基、C1-C6卤代烷氧基、C2-C6烯氧基、C2-C6炔氧基、C3-C10环烷氧基、C3-C10环烯氧基、C2-C6卤代烯氧基、C6-C20芳基、C3-C20杂环基、或NR6R7。
10.根据前述权利要求中任一项所述的具有化学式(I)的化合物的用途,其中R5是甲基、乙基异丙基、叔丁基或叔丁氧基。
11.根据权利要求1至6中任一项所述的具有化学式(I)的化合物的用途,其中R3和R5连同X2以及它们所连接的原子一起形成饱和或部分不饱和5-9元环系统,该5-9元环系统任选地包括1至3个独立地选自S、O和N的杂原子并且任选地被1至3个独立地选自卤素或C1-C6烷基的基团取代。
12.根据权利要求11所述的具有化学式(I)的化合物的用途,其中R3和R5连同X2和它们所附接的原子一起形成环系统T,该环系统T选自由T1和T2组成的组,
其中X2和R4是如权利要求1中所定义的,并且A表示与吡啶并/嘧啶并-吡唑部分的附接点。
13.根据前述权利要求中任一项所述的具有化学式(I)的化合物的用途,其中R4是O。
14.根据前述权利要求中任一项所述的具有化学式(I)的化合物的用途,其中X2是O,或NR8。
15.根据前述权利要求中任一项所述的具有化学式(I)的化合物的用途,其中R8是氢、氰基、C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、或C2-C6炔基。
16.根据前述权利要求中任一项所述的具有化学式(I)的化合物的用途,其中R9是氢、氯、氟、溴、甲基或三氟甲基。
17.根据前述权利要求中任一项所述的具有化学式(I)的化合物的用途,其中R9是氢或氯。
18.根据前述权利要求中任一项所述的具有化学式(I)的化合物的用途,其中R10是C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6烷基硫基、-C(O)OR6、C1-C6烷氧基、C1-C6卤代烷氧基、C3-C6环烷基、或C2-C6炔基。
19.根据前述权利要求中任一项所述的具有化学式(I)的化合物的用途,其中R10是C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、C1-C6烷氧基、C1-C6卤代烷氧基、C3-C6环烷基、-C(=O)OR6、或C2-C6炔基。
20.根据前述权利要求中任一项所述的具有化学式(I)的化合物的用途,其中R10是甲基、三氟甲基或二氟甲基。
21.一种除草组合物,该除草组合物包括按重量计从0.1%至99%的如在前述权利要求中任一项所定义的具有化学式(I)的化合物,以及按重量计从1%至99.9%的配制佐剂,其中该配制佐剂包括按重量计从0至25%的表面活性物质。
22.如权利要求21所述的除草组合物,该除草组合物进一步包括至少一种另外的选自除草剂或除草剂安全剂的杀有害生物剂。
23.根据权利要求22所述的除草组合物,其中该另外的杀有害生物剂选自下组,该组由以下各项组成:乙酰草胺、氟锁草醚、氟锁草醚钠、苯草醚、丙烯醛、甲草胺、阿洛昔芬、莠灭净、氨唑草酮、酰嘧磺隆、氯氨吡啶酸、杀草强、莎稗磷、黄草灵、莠去津、唑啶草酮、四唑嘧磺隆、BCPC、氟丁酰草胺、草除灵、苯卡巴腙、氟草胺、呋草磺、苄嘧磺隆、苄嘧磺隆甲酯、地散磷、灭草松、双苯嘧草酮、苯并双环酮、吡草酮、氟吡草酮、治草醚、双丙氨膦、双草醚、双草醚钠、硼砂、丁溴啶、溴丁酰草胺、溴草腈、丁草胺、丁胺磷、地乐胺、丁苯草酮、丁酸盐、卡可基酸、氯酸钙、唑草胺、长杀草、唑草酮、唑酮草酯、氯芴素、氯芴素甲酯、杀草敏、氯嘧磺隆、氯嘧磺隆乙酯、氯乙酸、绿麦隆、氯普芬、氯磺隆、敌草索、敌草索二甲酯、吲哚酮草酯、环庚草醚、醚磺隆、咯草隆、烯草酮、炔草酯、炔草酯炔丙酯、广灭灵、稗草胺、二氯吡啶酸、氯酯磺草胺、氯酯磺草胺甲酯、氰草津、环草敌、环丙嘧磺隆、噻草酮、氰氟草酯、氰氟草酯-丁基、2,4-D、杀草隆、茅草枯、棉隆、2,4-DB、甜菜安、麦草畏、敌草腈、2,4-滴丙酸、精2,4-滴丙酸、禾草灵、禾草灵甲酯、双氯磺草胺、野燕枯、野燕枯甲基磺酸盐、吡氟酰草胺、氟吡草腙、噁唑隆、哌草丹、二甲草胺、异戊净、二甲吩草胺、精二甲吩草胺、噻节因、二甲胂酸、敌乐胺、特乐酚、草乃敌、异丙净、敌草快、敌草快二溴化物、氟硫草定、敌草隆、草多索、EPTC、禾草畏、丁氟消草、胺苯磺隆、胺苯磺隆甲酯、乙烯利、甜菜呋、氟乳醚、乙氧嘧磺隆、乙氧苯草胺、精噁唑禾草灵、精噁唑禾草灵-乙酯、四唑酰草胺、硫酸亚铁、麦草氟M、啶嘧磺隆、双氟磺草胺、吡氟禾草灵、吡氟禾草灵丁酯、精吡氟禾草灵、精吡氟禾草灵-丁酯、异丙吡草酯、氟酮磺隆、氟酮磺隆-钠、氟吡磺隆、氟消草、氟噻草胺、氟哒嗪草酯、氟哒嗪草酯乙酯、氟节胺、唑嘧磺草胺、氟烯草酸、氟烯草酸戊酯、丙炔氟草胺、氟炔草胺、伏草隆、乙羧氟草醚、乙羧氟草醚乙酯、氟虫腙、氟胺草唑、氟替丙酸、四氟丙酸、氟啶嘧磺隆、氟啶嘧磺隆-甲基-钠、抑草丁、氟啶草酮、氟咯草酮、使它隆、呋草酮、嗪草酸、嗪草酸甲酯、氟磺胺草醚、甲酰胺磺隆、蔓草磷、草铵膦、草铵膦铵、草甘膦、氟氯吡啶酯、氯吡嘧磺隆、氯吡嘧磺隆甲酯、吡氟氯禾灵、精吡氟氯禾灵、环嗪酮、咪草酯、咪草酯甲酯、甲氧咪草烟、甲咪唑烟酸、灭草烟、咪唑喹啉酸、咪草烟、咪唑磺隆、茚草酮、三嗪茚草胺、碘甲烷、碘磺隆、碘甲磺隆钠、碘苯腈、异丙隆、异噁隆、异噁酰草胺、异噁氯草酮、异噁唑草酮、异噁草醚、卡灵草、克阔乐、环草定、利谷隆、2甲4氯丙酸、精2甲4氯丙酸、苯噻酰草胺、氟磺酰草胺、甲基二磺隆、甲基二磺隆甲酯、硝磺草酮、威百亩、噁唑酰草胺、苯嗪草酮、吡草胺、甲基苯噻隆、灭草唑、甲基胂酸、甲基杀草隆、异硫氰酸甲酯、异丙甲草胺、S-异丙甲草胺、磺草唑胺、甲氧隆、赛克嗪、甲磺隆、甲磺隆甲酯、草达灭、绿谷隆、萘丙胺、敌草胺、抑草生、草不隆、烟嘧磺隆、正甲基草甘膦、壬酸、达草灭、油酸、坪草丹、嘧苯胺磺隆、氨磺灵、丙炔噁草酮、噁草酮、环氧嘧磺隆、噁嗪草酮、乙氧氟草醚、百草枯、百草枯二氯化物、克草猛、二甲戊乐灵、五氟磺草胺、五氯苯酚、甲氯酰草胺、环戊噁草酮、烯草胺、甜菜宁、毒莠定、氟吡酰草胺、唑啉草酯、哌草磷、丙草胺、氟嘧磺隆、氟嘧磺隆甲酯、氨氟乐灵、环苯草酮、调环酸钙、扑灭通、扑草净、扑草胺、敌稗、喔草酯、扑灭津、苯胺灵、异丙草胺、丙苯磺隆、丙苯磺隆钠、拿草特、苄草丹、氟磺隆、双唑草腈、吡草醚、吡草醚乙酯、磺酰草吡唑、吡唑特、吡嘧磺隆、吡嘧磺隆乙酯、苄草唑、嘧啶肟草醚、稗草畏、氯苯咕醇、哒草特、环酯草醚、嘧草醚、嘧草醚甲酯、吡丙醚、嘧硫草醚、嘧硫草醚钠、罗克杀草砜、甲氧磺草胺、快杀稗、喹草酸、灭藻醌、喹禾灵、精喹禾灵、砜嘧磺隆、苯嘧磺草胺、稀禾定、环草隆、西玛津、西草净、氯酸钠、磺草酮、甲磺草胺、嘧磺隆、嘧磺隆甲酯、草硫膦、磺酰磺隆、硫酸、丁噻隆、特呋三酮、环磺酮、吡喃草酮、特草定、甲氧去草净、特丁津、去草净、甲氧噻草胺、噻草啶、噻吩磺隆、噻酮磺隆、噻吩磺隆甲酯、禾草丹、苯吡唑草酮、肟草酮、野麦畏、醚苯磺隆、三嗪氟草胺、苯磺隆、苯磺隆甲酯、绿草定、草达津、三氟啶磺隆、三氟啶磺隆钠、氟乐灵、氟胺磺隆、氟胺磺隆甲酯、三羟基三嗪、抗倒酯乙酯、三氟甲磺隆以及[3-[2-氯-4-氟-5-(1-甲基-6-三氟甲基-2,4-二氧代-1,2,3,4-四氢嘧啶-3-基)苯氧基]-2-吡啶基氧基]乙酸乙酯。
24.一种控制不想要的植物生长的方法,该方法包括将如在权利要求1至20中任一项所定义的具有化学式(I)的化合物或根据权利要求21至23中任一项所述的除草组合物施用至不想要的植物或施用至其所在场所。
25.一种在包括作物植物和杂草的场所选择性地控制杂草的方法,其中该方法包括:向该场所施用杂草控制量的如在权利要求1至20中任一项所定义的具有化学式(I)的化合物,或如在权利要求21至23中任一项所定义的组合物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1502164.5 | 2015-02-10 | ||
GBGB1502164.5A GB201502164D0 (en) | 2015-02-10 | 2015-02-10 | Herbicidal compounds |
PCT/EP2016/052232 WO2016128266A1 (en) | 2015-02-10 | 2016-02-03 | Herbicidal compounds |
Publications (2)
Publication Number | Publication Date |
---|---|
CN107250127A true CN107250127A (zh) | 2017-10-13 |
CN107250127B CN107250127B (zh) | 2020-11-24 |
Family
ID=52746382
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201680009376.6A Expired - Fee Related CN107250127B (zh) | 2015-02-10 | 2016-02-03 | 除草化合物 |
Country Status (7)
Country | Link |
---|---|
US (1) | US10905123B2 (zh) |
EP (1) | EP3255989B1 (zh) |
CN (1) | CN107250127B (zh) |
BR (1) | BR112017017193A2 (zh) |
ES (1) | ES2836423T3 (zh) |
GB (1) | GB201502164D0 (zh) |
WO (1) | WO2016128266A1 (zh) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108013040A (zh) * | 2017-12-08 | 2018-05-11 | 北京科发伟业农药技术中心 | 含苯嘧磺草胺和精敌草胺的除草组合物 |
CN108077283A (zh) * | 2017-12-22 | 2018-05-29 | 北京科发伟业农药技术中心 | 含唑啉草酯和磺酰草吡唑的除草组合物 |
CN113423272A (zh) * | 2019-02-15 | 2021-09-21 | 先正达农作物保护股份公司 | 除草组合物 |
CN113453554A (zh) * | 2019-02-15 | 2021-09-28 | 先正达农作物保护股份公司 | 除草组合物 |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20190327969A1 (en) * | 2016-03-23 | 2019-10-31 | Syngenta Participations Ag | Herbicides |
US10743535B2 (en) | 2017-08-18 | 2020-08-18 | H&K Solutions Llc | Insecticide for flight-capable pests |
GB201715324D0 (en) * | 2017-09-22 | 2017-11-08 | Syngenta Participations Ag | Improvements in or relating to organic compounds |
GB201715414D0 (en) * | 2017-09-22 | 2017-11-08 | Syngenta Participations Ag | Improvements in or relating to organic compounds |
MX2021009954A (es) | 2019-02-19 | 2021-12-10 | Gowan Company L L C | Composiciones liquidas estables y metodos para usar las mismas. |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013162715A2 (en) * | 2012-04-27 | 2013-10-31 | Dow Agrosciences Llc | Pesticidal compositions and processes related thereto |
CN103619171A (zh) * | 2010-11-03 | 2014-03-05 | 陶氏益农公司 | 杀虫组合物和与其相关的方法 |
JP2014111559A (ja) * | 2012-07-04 | 2014-06-19 | Nissan Chem Ind Ltd | ピラゾール誘導体および有害生物防除剤 |
US20140213448A1 (en) * | 2012-04-27 | 2014-07-31 | Dow Agrosciences Llc | Pesticidal compositions and processes related thereto |
CN104010505A (zh) * | 2011-10-26 | 2014-08-27 | 陶氏益农公司 | 杀虫组合物和与其相关的方法 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20130126606A (ko) | 2010-11-03 | 2013-11-20 | 다우 아그로사이언시즈 엘엘씨 | 살충 조성물 및 이에 관련된 방법 |
-
2015
- 2015-02-10 GB GBGB1502164.5A patent/GB201502164D0/en not_active Ceased
-
2016
- 2016-02-03 ES ES16702570T patent/ES2836423T3/es active Active
- 2016-02-03 CN CN201680009376.6A patent/CN107250127B/zh not_active Expired - Fee Related
- 2016-02-03 EP EP16702570.9A patent/EP3255989B1/en active Active
- 2016-02-03 US US15/549,707 patent/US10905123B2/en active Active
- 2016-02-03 BR BR112017017193A patent/BR112017017193A2/pt not_active IP Right Cessation
- 2016-02-03 WO PCT/EP2016/052232 patent/WO2016128266A1/en active Application Filing
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103619171A (zh) * | 2010-11-03 | 2014-03-05 | 陶氏益农公司 | 杀虫组合物和与其相关的方法 |
CN104010505A (zh) * | 2011-10-26 | 2014-08-27 | 陶氏益农公司 | 杀虫组合物和与其相关的方法 |
WO2013162715A2 (en) * | 2012-04-27 | 2013-10-31 | Dow Agrosciences Llc | Pesticidal compositions and processes related thereto |
US20140213448A1 (en) * | 2012-04-27 | 2014-07-31 | Dow Agrosciences Llc | Pesticidal compositions and processes related thereto |
JP2014111559A (ja) * | 2012-07-04 | 2014-06-19 | Nissan Chem Ind Ltd | ピラゾール誘導体および有害生物防除剤 |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108013040A (zh) * | 2017-12-08 | 2018-05-11 | 北京科发伟业农药技术中心 | 含苯嘧磺草胺和精敌草胺的除草组合物 |
CN108077283A (zh) * | 2017-12-22 | 2018-05-29 | 北京科发伟业农药技术中心 | 含唑啉草酯和磺酰草吡唑的除草组合物 |
CN113423272A (zh) * | 2019-02-15 | 2021-09-21 | 先正达农作物保护股份公司 | 除草组合物 |
CN113453554A (zh) * | 2019-02-15 | 2021-09-28 | 先正达农作物保护股份公司 | 除草组合物 |
CN113453554B (zh) * | 2019-02-15 | 2023-09-05 | 先正达农作物保护股份公司 | 除草组合物 |
Also Published As
Publication number | Publication date |
---|---|
EP3255989A1 (en) | 2017-12-20 |
CN107250127B (zh) | 2020-11-24 |
GB201502164D0 (en) | 2015-03-25 |
ES2836423T3 (es) | 2021-06-25 |
US10905123B2 (en) | 2021-02-02 |
WO2016128266A1 (en) | 2016-08-18 |
BR112017017193A2 (pt) | 2018-06-26 |
US20180027815A1 (en) | 2018-02-01 |
EP3255989B1 (en) | 2020-09-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN107250127A (zh) | 除草化合物 | |
CN106536486B (zh) | 除草哒嗪酮衍生物 | |
RU2697417C1 (ru) | Пиразолоновые соединения или их соли, способ их получения, гербицидная композиция и ее применение | |
CN107001349A (zh) | 除草吡啶并/嘧啶并噻唑 | |
CN105451558B (zh) | 吡唑基吡咯啉酮及其作为除草剂的用途 | |
RU2739914C2 (ru) | Гербициды | |
AU2013251862A1 (en) | Pyridazinone herbicidal compounds | |
CH655310A5 (fr) | Derives acylamino du n-phenylpyrazole, compositions les contenant et leur utilisation comme herbicides. | |
CN108884074A (zh) | 除草哒嗪酮化合物 | |
CN108884069A (zh) | 除草剂 | |
CN103974616A (zh) | 除草剂组合物 | |
CN106661010A (zh) | 除草化合物 | |
CN105472986A (zh) | 吡唑基吡咯啉酮及其作为除草剂的用途 | |
CN109836391A (zh) | 异噁唑啉衍生物及其在农业中的应用 | |
RU2760349C2 (ru) | Гербициды | |
CN108929319A (zh) | 异噁唑啉衍生物及其在农业中的应用 | |
CN105683189B (zh) | 除草的3‑(2‑苄氧基苯基)‑2,4‑二羟基‑1,8‑萘啶衍生物 | |
CN106795101B (zh) | 除草化合物 | |
CN105121410B (zh) | 除草活性2-(取代的-苯基)-环戊烷-1,3-二酮化合物及其衍生物 | |
CN111212568B (zh) | 除草活性的吡啶基-/嘧啶基-嘧啶衍生物 | |
JP7153068B2 (ja) | 除草剤としてのピラジン-4-カルバメート又は尿素誘導体 | |
JP7206262B2 (ja) | 除草活性を有するピリジル-/ピリミジル-ピラジン誘導体 | |
JP7252215B2 (ja) | 除草剤としてのピリミジン-4-カルバメート又は尿素誘導体 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20201124 |
|
CF01 | Termination of patent right due to non-payment of annual fee |