CN1289330A - 用作除草剂的取代的杂芳基甲基化合物 - Google Patents
用作除草剂的取代的杂芳基甲基化合物 Download PDFInfo
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- CN1289330A CN1289330A CN99802547A CN99802547A CN1289330A CN 1289330 A CN1289330 A CN 1289330A CN 99802547 A CN99802547 A CN 99802547A CN 99802547 A CN99802547 A CN 99802547A CN 1289330 A CN1289330 A CN 1289330A
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- amino
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- alkyl
- base
- carbonyl
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 61
- 239000004009 herbicide Substances 0.000 title abstract description 5
- -1 nitro, formyl Chemical group 0.000 claims description 169
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 48
- 238000002360 preparation method Methods 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 239000011737 fluorine Substances 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 13
- 239000000460 chlorine Substances 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000002252 acyl group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000003368 amide group Chemical group 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 7
- JSLZUBLGGPEVQN-DIPNUNPCSA-N (2r)-4-methyl-2-propan-2-yl-2-[2-[4-[4-[2-(3,4,5-trimethoxyphenyl)ethyl]piperazin-1-yl]butoxy]phenyl]-1,4-benzothiazin-3-one Chemical compound COC1=C(OC)C(OC)=CC(CCN2CCN(CCCCOC=3C(=CC=CC=3)[C@@]3(C(N(C)C4=CC=CC=C4S3)=O)C(C)C)CC2)=C1 JSLZUBLGGPEVQN-DIPNUNPCSA-N 0.000 claims description 6
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 6
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 6
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 6
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 6
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 6
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
- 229950001891 iprotiazem Drugs 0.000 claims description 6
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 6
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 6
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 6
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000005493 quinolyl group Chemical group 0.000 claims description 6
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 6
- 125000001425 triazolyl group Chemical group 0.000 claims description 6
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 claims description 5
- 150000001345 alkine derivatives Chemical class 0.000 claims description 5
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000005108 alkenylthio group Chemical group 0.000 claims description 4
- 125000001118 alkylidene group Chemical group 0.000 claims description 4
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 230000002363 herbicidal effect Effects 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 4
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- PFJOTFSIBVZGPK-UHFFFAOYSA-N 1-ethyl-2-methylhydrazine Chemical compound CCNNC PFJOTFSIBVZGPK-UHFFFAOYSA-N 0.000 claims description 2
- WAUHABGEEBVFTF-UHFFFAOYSA-N CCCC[S] Chemical group CCCC[S] WAUHABGEEBVFTF-UHFFFAOYSA-N 0.000 claims description 2
- TWBIDQDUOXHFSN-UHFFFAOYSA-N C[CH]C=O Chemical compound C[CH]C=O TWBIDQDUOXHFSN-UHFFFAOYSA-N 0.000 claims description 2
- 239000004606 Fillers/Extenders Substances 0.000 claims description 2
- NRAINUFKKPBZQY-UHFFFAOYSA-N [O]C1CC1 Chemical compound [O]C1CC1 NRAINUFKKPBZQY-UHFFFAOYSA-N 0.000 claims description 2
- GYAPJISEIGCPQO-UHFFFAOYSA-N [O]C1CCC1 Chemical compound [O]C1CCC1 GYAPJISEIGCPQO-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000006323 alkenyl amino group Chemical group 0.000 claims description 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 2
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- VCZIFQMEDXLHEA-UHFFFAOYSA-N cyclopentylperoxycyclohexane Chemical compound C1(CCCC1)OOC1CCCCC1 VCZIFQMEDXLHEA-UHFFFAOYSA-N 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 230000005611 electricity Effects 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 2
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 238000006722 reduction reaction Methods 0.000 claims description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 4
- RQQDJYROSYLPPK-UHFFFAOYSA-N N1=CC=CC2=CC=CC=C21.N1=CC=CC2=CC=CC=C21 Chemical compound N1=CC=CC2=CC=CC=C21.N1=CC=CC2=CC=CC=C21 RQQDJYROSYLPPK-UHFFFAOYSA-N 0.000 claims 3
- 150000001721 carbon Chemical group 0.000 claims 2
- 125000004647 alkyl sulfenyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 241000196324 Embryophyta Species 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000002994 raw material Substances 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 12
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
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- 239000000706 filtrate Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
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- PHNUZKMIPFFYSO-UHFFFAOYSA-N propyzamide Chemical compound C#CC(C)(C)NC(=O)C1=CC(Cl)=CC(Cl)=C1 PHNUZKMIPFFYSO-UHFFFAOYSA-N 0.000 description 1
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- YXIIPOGUBVYZIW-UHFFFAOYSA-N pyraflufen Chemical compound ClC1=C(OC(F)F)N(C)N=C1C1=CC(OCC(O)=O)=C(Cl)C=C1F YXIIPOGUBVYZIW-UHFFFAOYSA-N 0.000 description 1
- ASRAWSBMDXVNLX-UHFFFAOYSA-N pyrazolynate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OS(=O)(=O)C1=CC=C(C)C=C1 ASRAWSBMDXVNLX-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- VTRWMTJQBQJKQH-UHFFFAOYSA-N pyributicarb Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C(C=CC=2)C(C)(C)C)=N1 VTRWMTJQBQJKQH-UHFFFAOYSA-N 0.000 description 1
- DEIKMOQTJBGGAX-DJKKODMXSA-N pyriminobac Chemical compound CO\N=C(/C)C1=CC=CC(OC=2N=C(OC)C=C(OC)N=2)=C1C(O)=O DEIKMOQTJBGGAX-DJKKODMXSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 description 1
- ALZOLUNSQWINIR-UHFFFAOYSA-N quinmerac Chemical compound OC(=O)C1=C(Cl)C=CC2=CC(C)=CN=C21 ALZOLUNSQWINIR-UHFFFAOYSA-N 0.000 description 1
- OSUHJPCHFDQAIT-GFCCVEGCSA-N quizalofop-P-ethyl Chemical group C1=CC(O[C@H](C)C(=O)OCC)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 OSUHJPCHFDQAIT-GFCCVEGCSA-N 0.000 description 1
- BBKDWPHJZANJGB-IKJXHCRLSA-N quizalofop-P-tefuryl Chemical group O=C([C@H](OC=1C=CC(OC=2N=C3C=CC(Cl)=CC3=NC=2)=CC=1)C)OCC1CCCO1 BBKDWPHJZANJGB-IKJXHCRLSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000003516 soil conditioner Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- OORLZFUTLGXMEF-UHFFFAOYSA-N sulfentrazone Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(NS(C)(=O)=O)=C(Cl)C=C1Cl OORLZFUTLGXMEF-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920001059 synthetic polymer Polymers 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
- RJKCKKDSSSRYCB-UHFFFAOYSA-N tebutam Chemical compound CC(C)(C)C(=O)N(C(C)C)CC1=CC=CC=C1 RJKCKKDSSSRYCB-UHFFFAOYSA-N 0.000 description 1
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 description 1
- WOSNCVAPUOFXEH-UHFFFAOYSA-N thifluzamide Chemical compound S1C(C)=NC(C(F)(F)F)=C1C(=O)NC1=C(Br)C=C(OC(F)(F)F)C=C1Br WOSNCVAPUOFXEH-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 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 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
-
- 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
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Abstract
本发明涉及通式(Ⅰ)的取代的杂芳基甲基化合物,其中,Q、X1、X2、Z1和Z2具有说明书中给出的含义,本发明还涉及它们的制法及它们作为除草剂的应用。
Description
本发明涉及新颖的取代的杂芳基甲基化合物,其制备方法及其作为除草剂的应用。
取代的芳基甲基化合物类作为潜在的除草剂业已公开于(专利)文献中(参见,DE-A-2526358、US-A-4249934、US-A-5262390、WO-A-9621647)。然而,这些化合物迄今未获得任何实际的重要性。
因此,本发明提供新颖的通式(Ⅰ)的取代的杂芳基甲基化合物其中Q 代表O、S、SO或SO2,X1 代表氢、羟基、巯基、氨基、硝基、甲酰基、羧基、氰基、氨基甲
酰基、硫代氨基甲酰基、卤素,或代表均可任选由氰基-、卤素-或
烷氧基取代的烷基、烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、
烷基氨基、二烷基氨基、烷基羰基、烷氧基羰基、烷基羰基氨基、
烷氧基羰基氨基或烷基磺酰基氨基,X2 代表氢或卤素,Z1 代表任选取代的选自下列的杂芳基:呋喃基、苯并呋喃基、吡咯基、
吡唑基、咪唑基、三唑基、噁唑基、异噁唑基、苯并噁唑基、噻唑
基、异噻唑基、苯并噻唑基、苯并咪唑基、吡啶基、喹啉基、异喹
取代的烷基、烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷基
氨基、二烷基氨基、链烯基、链烯氧基、链烯硫基、链烯氨基、炔
基、炔氧基、炔硫基、环烷基、环烷基氧基、环烷基硫基或环烷基
氨基,或任选与相邻的R1一起代表烷二基(亚烷基),和R2 代表氢、氰基、甲酰基,或代表均可任选由氰基-、卤素-或烷氧基
-取代的烷基、烷基羰基、烷氧基羰基、链烯基或炔基。
在上述定义中,烃链如烷基-以及在与杂原子组合时,如在烷氧基中-均可是直链或支链。
本发明优选提供式(Ⅰ)化合物,其中Q 代表O、S、SO或SO2,X1 代表氢、羟基、巯基、氨基、硝基、甲酰基、羧基、氰基、氨基甲
酰基、硫代氨基甲酰基、卤素,或任选由氰基-、卤素-或C1-C4-烷
氧基-取代的各在烷基中具有1至6个碳原子的烷基、烷氧基、烷
硫基、烷基亚磺酰基、烷基磺酰基、烷基氨基、二烷基氨基、烷基
羰基、烷氧基羰基、烷基羰基氨基、烷氧基羰基氨基或烷基磺酰基
氨基,X2 代表氢或卤素,Z1 代表任选取代的选自下列的杂芳基:呋喃基、苯并呋喃基、吡咯基、
吡唑基、咪唑基、三唑基、噁唑基、异噁唑基、苯并噁唑基、噻唑
基、异噻唑基、苯并噻唑基、苯并咪唑基、吡啶基、喹啉基、异喹
啉基、嘧啶基、吡嗪基、哒嗪基、喹唑啉基或喹喔啉基,其中可能
的取代基优选选自下列:
硝基、氨基、羟基、羧基、氰基、氨基甲酰基、硫代氨基甲酰基、
磺基、氯代磺酰基、氨基磺酰基、卤素,均可任选由氰基-、卤素-
或C1-C4-烷氧基-取代的各在烷基部分具有1至4个碳原子的烷基、
烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷基氨基、烷基羰
基、烷氧基羰基、烷基氨基羰基、烷基羰基氨基、烷氧基羰基氨基
或烷基磺酰基氨基,或苯基,
基-取代的在烷基部分各具有1至6个碳原子的烷基、烷氧基、烷
硫基、烷基亚磺酰基、烷基磺酰基、烷基氨基或二烷基氨基,代表
均可任选由卤素取代的各在链烯基或炔基部分具有2至6个碳原子
的链烯基、链烯氧基、链烯硫基、链烯基氨基、炔基、炔氧基或炔
硫基,代表均可任选由氰基-、卤素-或C1-C4-烷氧基-取代的各在
环烷基中具有3至6个碳原子的环烷基、环烷基氧基、环烷基硫基
或环烷基氨基,或任选与相邻的R1一起代表具有3至5个碳原子的
烷二基(亚烷基),和R2 代表氢、氰基、甲酰基,代表均可任选由氰基-、卤素-或C1-C4-烷
氧基-取代的各在烷基中具有1至6个碳原子的烷基、烷基羰基、
烷氧基羰基,或代表均可任选由卤素取代的各具有3至6个碳原子
的链烯基或炔基。
本发明特别是涉及式(Ⅰ)化合物,其中Q 代表O、S、SO或SO2,X1 代表氢、羟基、巯基、氨基、硝基、甲酰基、羧基、氰基、氨基甲
酰基、硫代氨基甲酰基、氟、氯、溴,代表均可任选由氰基-、氟-、
氯-、甲氧基-或乙氧基-取代的甲基、乙基、正或异丙基、甲氧基、
乙氧基、正或异丙氧基、甲硫基、乙硫基、正或异丙硫基、甲基亚
磺酰基、乙基亚磺酰基、甲基磺酰基、乙基磺酰基、甲基氨基、乙
基氨基、正或异丙基氨基、二甲基氨基、二乙基氨基、乙酰基、丙
酰基、甲氧基羰基、乙氧基羰基、乙酰基氨基、丙酰基氨基、甲氧
基羰基氨基、乙氧基羰基氨基、甲基磺酰基氨基、乙基磺酰基氨基、
正或异丙基磺酰基氨基,X2 代表氢、氟、氯或溴,Z1 代表任选取代的选自下列的杂芳基:呋喃基、苯并呋喃基、吡咯基、
吡唑基、咪唑基、三唑基、噁唑基、异噁唑基、苯并噁唑基、噻唑
基、异噻唑基、苯并噻唑基、苯并咪唑基、吡啶基、喹啉基、异喹
啉基、嘧啶基、吡嗪基、哒嗪基、喹唑啉基或喹喔啉基,其中可能
的取代基优选选自下列:
硝基、氨基、羟基、羧基、氰基、氨基甲酰基、硫代氨基甲酰基、
氨基磺酰基、氟、氯、溴,均可任选由氰基-、氟-、氯-、甲氧基-
或乙氧基-取代的甲基、乙基、正或异丙基、正-、异-、仲-或叔丁
基、甲氧基、乙氧基、正或异丙氧基、正-、异-、仲-或叔丁氧基、
甲硫基、乙硫基、正或异丙硫基、正-、异-、仲-或叔丁硫基、甲
基亚磺酰基、乙基亚磺酰基、甲基磺酰基、乙基磺酰基、甲基氨基、
乙基氨基、正或异丙基氨基、正-、异-、仲-或叔丁基氨基、乙酰
基、丙酰基、正或异丁酰基、甲氧基羰基、乙氧基羰基、正或异丙
氧基羰基、甲基氨基羰基、乙基氨基羰基、正或异丙基氨基羰基、
乙酰基氨基、丙酰基氨基、正-或异丁酰基氨基、甲氧基羰基氨基、
乙氧基羰基氨基、正或异丙氧基羰基氨基、甲基磺酰基氨基、乙基
磺酰基氨基、正或异丙基磺酰基氨基、正-、异-、仲-或叔丁基磺
酰基氨基,或苯基,和Z2 代表下列基团之一
其中
Q1代表O或S,R1 代表氢、氰基、氟、氯、溴,或代表均可任选由氰基-、氟、氯-、
甲氧基-或乙氧基-取代的甲基、乙基、正或异丙基、甲氧基、乙氧
基、正或异丙氧基、甲硫基、乙硫基、正或异丙硫基、甲基亚磺酰
基、乙基亚磺酰基、甲基磺酰基、乙基磺酰基、甲基氨基、乙基氨
基、正或异丙基氨基、二甲基氨基或二乙基氨基,代表均可任选由
氟-、氯-或溴-取代的乙烯基、丙烯基、丙烯基氧基、丙烯基硫基、
丙烯基氨基、乙炔基、丙炔基、丙炔基氧基或丙炔基硫基,或代表
均可任选由氰基-、氟-、氯-、甲基-、乙基-、正-或异丙基-取代
的环丙基、环丁基、环戊基、环己基、环丙基氧基、环丁基氧基、
环戊基氧基、环己基氧基、环丙基氨基、环丁基氨基、环戊基氨基
或环己基氨基,或任选与相邻R1一起代表丙-1,3-二基(三亚甲基)
或丁-1,4-二基(四亚甲基),和R2 代表氢、氰基、甲酰基,代表均可任选由氰基-、氟-、氯-、甲氧
基-或乙氧基-取代的甲基、乙基、正或异丙基、乙酰基、丙酰基、
正或异丁酰基、甲氧基羰基、乙氧基羰基、正或异丙氧基羰基,或
代表均可任选由氟-、氯-或溴-取代的丙烯基、丁烯基、丙炔基或
丁炔基。
一组非常特别优选的通式(Ⅰ)化合物是这样的化合物,其中Z2代表下式的杂环基且Q、X1、X2与Z1和R2具有上面给出的特别优选的含义,
Q、X1、X2、Z1和Z2具有表1(制备实施例之后)中给出的含义,以及制备实施例1和2的化合物。
上面提到的一般或优选的基团定义适合于式(Ⅰ)终产物,且相应地,也适合于在每一种制备情况下所需的起始原料或中间体。这些基团定义可以按照需要相互结合,即,包括上面提到的优选范围间的组合。
新颖的通式(Ⅰ)的取代的杂芳基甲基化合物具有强的和选择性的除草活性。
新颖的通式(Ⅰ)的取代的杂芳基甲基化合物如下获得:
(a)如果适合在稀释剂存在下和如果适合在反应辅助剂存在下,
其中
Q、X1、X2和Z1如上所定义,
或
(b)如果适合在稀释剂存在下和如果适合在反应辅助剂存在下,
其中
Q、X1、X2和Z2各如上所定义,
与通式(Ⅳ)的杂芳基甲基卤反应
X3-CH2-Z1 (Ⅳ)
其中
Z1如上所定义,和
X3代表卤素,
或
(c)如果适合在反应辅助剂存在下和在如果适合在稀释剂存在下,
其中
X1、X2和Z2各如上所定义,和
X4代表卤素,
与通式(Ⅵ)的杂芳烃反应,
HQ-CH2-Z1 (Ⅵ)
其中
Q和Z1如上所定义,
如果适合,随后用常规方式在取代基定义的范围内进行亲电或亲核取代反应以及/或氧化反应或还原反应。
使用,例如,邻苯二甲酸酐和1-氨基-2-氟-4-(3,5-二甲基-异噁唑-4-基-甲氧基)-苯作为作为起始原料,本发明方法(a)中的反应途径可以用下列反应式来说明:
使用,例如,3-(2,4-二氟-5-硝基-苯基)-4-溴-1-甲基-5-三氟甲基-1H-吡唑和糠醇作为起始原料,本发明方法(c)中的反应途径可以用下列反应式来说明:
意欲在本发明制备式(Ⅰ)化合物的方法中用作起始原料的邻苯二甲酸酐和3,4,5,6-四氢-邻苯二甲酸酐是合成上已知的有机化学品。
式(Ⅱ)提供在制备式(Ⅰ)化合物的本发明方法(a)中用作起始原料的氨基苯衍生物的一般定义。在式(Ⅱ)中,Q、X1、X2和Z1各优选或特别是具有在上文有关本发明式(Ⅰ)化合物的描述中业已提到的Q、X1、X2和Z1的优选或特别优选的含义。
通式(Ⅱ)起始原料是已知和/或可以通过已知的方法制备(参见,《Justus Liebigs Ann.Chem.733(1970),125-140;DE-A-2842186;US-A-5344812;US-A-5399543;WO-A-9517096;制备实施例)。
通式(Ⅲ)提供在本发明方法(b)中用作起始原料的取代的杂环基芳烃的一般定义。在式(Ⅲ)中,Q、X1、X2和Z2各优选或特别是具有在上文有关本发明式(Ⅰ)化合物的描述中业已提到的Q、X1、X2和Z2的优选或特别优选的含义。
式(Ⅲ)起始原料是已知和/或可以由本身已知的方法制备(参见,EP-A-545206;JP-A-04178373;WO-A-9618618;制备实施例)
式(Ⅳ)提供在制备式(Ⅰ)化合物的本发明方法(b)中用作起始原料的杂芳基甲基卤的一般定义。在式(Ⅳ)中,Z1各优选或特别是具有在上文有关本发明式(Ⅰ)化合物的描述中业已提到的Z1的优选或特别优选的含义;X3优选代表氟、氯、溴或碘,特别是氯或溴。
式(Ⅳ)起始原料是合成上已知的有机化学品。
通式(Ⅴ)提供在制备式(Ⅰ)化合物的本发明方法(c)中用作起始原料的取代的杂环基芳烃的一般定义。在式(Ⅴ)中,X1、X2和Z2各优选或特别是具有在上文有关本发明式(Ⅰ)化合物的描述中业已提到的X1、X2和Z2的优选或特别优选的含义;X4优选代表氟、氯或溴,特别是氟或氯。
式(Ⅴ)起始原料是已知的和/或可以用本身已知的方法制备(参见,US-A-5281571,WO-A-9206962;WO-A-9618618)。
式(Ⅵ)提供在制备式(Ⅰ)化合物的本发明方法(c)中另一用作起始原料的杂芳烃的一般定义。在式(Ⅵ)中,Q和Z1各优选或特别是具有在上文有关本发明式(Ⅰ)化合物的描述中业已提到的Q和Z1的优选或特别优选的含义。
式(Ⅵ)起始原料是合成上已知的有机化学品。
本发明制备通式(Ⅰ)方法优选使用稀释剂进行。适合于进行本发明方法(a)至(c)的稀释剂首先是惰性有机溶剂。这些物质包括特别是脂肪族、脂环族或芳族的任选卤代的烃,诸如,例如汽油、苯、甲苯、二甲苯、氯苯、二氯苯、石油醚、己烷、环己烷、二氯甲烷、氯仿、四氯化碳;醚类,如乙醚、异丙醚、二噁烷、四氢呋喃或乙二醇二甲醚或乙二醇二乙醚;酮类,如丙酮、丁酮或甲基异丁酮;腈类,如乙腈、丙腈或丁腈;酰胺类,如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基-甲酰苯胺、N-甲基吡咯烷酮或六甲基磷酰三胺;酯类,如乙酸甲酯或乙酸乙酯;亚砜类,如二甲基亚砜;醇类,如甲醇、乙醇、正-或异丙醇、乙二醇单甲醚、乙二醇单乙醚、二乙二醇单甲醚、二乙二醇单乙醚,它们与水的混合物,或纯水。
适合于方法(a)至(c)的反应辅助剂通常是常规的无机或有机碱或酸受体。这些物质优选包括碱金属或碱土金属的乙酸盐、氨化物、碳酸盐、碳酸氢盐、氢化物、氢氧化物或醇盐,如乙酸钠、乙酸钾或乙酸钙、氨化锂、氨化钠、氨化钾或氨化钙、碳酸钠、碳酸钾或碳酸钙、碳酸氢钠、碳酸氢钾或碳酸氢钙、氢化锂、氢化钠、氢化钾或氢化钙、氢氧化锂、氢氧化钠、氢氧化钾或氢氧化钙,甲醇、乙醇、正或异丙醇、正-、异-、仲-或叔丁醇的钠盐或甲醇、乙醇、正-或异丙醇、正-、异-、仲-或叔丁醇的钾盐;另外还有碱性有机氮化合物,如,三甲胺、三乙胺、三丙胺、三丁胺、乙基-二异丙胺、N,N-二甲基-环己基胺、二环己基胺、乙基-二环己基胺、N,N-二甲基苯胺、N,N-二甲基-苄基胺、吡啶,2-甲基-、3-甲基-、4-乙基-、2,4-二甲基-、2,6-二甲基-、3,4-二甲基-和3,5-二甲基-吡啶,5-乙基-2-甲基-吡啶、4-二甲基氨基-吡啶、N-甲基-哌啶、1,4-二氮杂二环[2.2.2]-辛烷(DABCO)、1,5-二氮杂二环[4.3.0]-壬-5-烯(DBN)或1,8-二氮杂二环[5.4.0]-十一-7-烯(DBU)。
进行本发明方法(a)至(c)时,反应温度可以在相对宽的范围内进行的。通常,反应是在0℃至200℃,优选在10℃至150℃间的温度下进行。
本发明的方法(a)至(c)通常是在常压下进行的。然而,本发明方法也可以在加压或减压下--通常是在0.1巴至10巴间的压力下进行。
进行本发明方法(a)至(c)时,通常采用大致等摩尔量的起始原料。然而,也可以相对大地过量采用反应组分之一。反应通常是在适合的稀释剂中,在反应辅助剂存在下进行的,且反应混合物通常在所需的温度下搅拌几小时。后处理是用常规方法进行(参见,制备实施例)。
本发明活性化合物可以用作脱叶剂、干燥剂、杀茎杆剂,和特别是用作除草剂。所谓的杂草,就其最广义而言,应理解为生长在不该生长的地方的所有植物。本发明的物质是作为灭生性除草剂或是选择性除草剂基本上取决于所用的量。
本发明化合物可以与例如下列植物相关使用:
下列属的双子叶杂草:芥属、独行草属、猪殃殃属、繁缕属、母菊属、春黄菊属、牛膝属、藜属、荨麻属、千里光属、苋属、马齿苋属、苍耳属、旋花属、甘薯属、蓼属、田菁属、豚草属、蓟属、飞廉属、苦苣菜属、茄属、焊菜属、节节草属、母草属、野芝麻属、婆婆纳属、苘麻属、刺酸模属、曼陀罗属、堇菜属、鼬瓣花属、罂粟属、矢车菊属、三叶草属、毛茛属、蒲公英属,
下列属的双子叶作物:棉属、大豆属、甜菜属、胡萝卜属、菜豆属、豌豆属、茄属、亚麻属、甘薯属、巢菜属、烟草属、蕃茄属、花生属、芸苔属、莴苣属、黄瓜属、南瓜属,
下列属的单子叶杂草:稗属、狗尾草属、黍属、马唐属、梯牧草属、早熟禾属、羊茅属、蟋蟀草属、臂形草属、黑麦草属、雀麦属、燕麦属、莎草属、高梁属、冰草属、狗牙根属、雨久花属、飘拂草属、慈菇属、荸荠属、藨草属、雀稗属、鸭嘴草属、尖瓣花属、龙爪茅属、剪股颖属、看麦娘属、风草属,
下列属的单子叶作物:稻属、玉米属、小麦属、大麦属、燕麦属、黑麦属、高梁属、黍属、甘蔗属、凤梨属、天门冬属、葱属。
然而,本发明活性化合物的应用决不限于这些属,且也可以相同的方式延伸至其它植物。
取决于化合物的浓度,化合物适合于灭生性防治杂草,例如工业地域和铁道线,以及有或无种植树林的道路和广场。同样,化合物可以用于防治多年生作物中的杂草,例如森林、装饰树林、果园、葡萄园、柑桔林、坚果园、蕉种植园、咖啡种植园、茶园、橡胶种植园、油棕榈种植园、可可种植园、软果林和啤酒花田、草场、体育场和牧场中的杂草。且本发明化合物还可以用于选择性地防治一年生作物中的杂草。
本发明式(Ⅰ)化合物特别适合于以芽前和芽后二种方式选择性地防治单子叶叶和双子叶作物中的单子叶和双子叶杂草。
活性化合物可以转化成常规的制剂,如溶液、乳剂、可湿性粉剂、悬浮剂、粉剂、喷粉剂、膏剂、可溶性粉剂、颗粒剂、悬乳剂、用活性化合物浸渍的天然或合成材料,以及包在聚合物中的微细胶囊。
这些制剂可以用已知的方式生产,例如,将活性化合物与扩充剂,即液体和/或与固体载体混合,并任选使用表面活性剂,即乳化剂和/或分散剂和/或起泡剂。
在用水作增充剂的情况下,也可以用有机溶剂作助溶剂。适合的液体溶剂主要有:芳族化合物,如二甲苯,甲苯或烷基萘,氯代芳族化合物或氯代脂肪烃,如氯代苯类、氯乙烯类或二氯甲烷,脂族烃,如环己烷或石蜡,例如石油馏份、矿物和植物油,醇类,如丁醇或甘醇以及其醚和酯,酮类,如丙酮、甲乙酮、甲基异丁基酮或环己酮,强极性溶剂,如二甲基甲酰胺或二甲基亚砜,以及水。
适合的固体载体是:例如铵盐和磨碎的天然矿物质,如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱石或硅藻土,和磨碎的合成矿物质,如高分散二氧化硅、矾土和硅酸盐,适合用于颗粒剂的固体载体有:例如压碎并分级的天然矿物质如方解石、大理石、浮石、海泡石和白云石,以及有机和无机粉的合成颗粒,和如下有机物的颗粒:锯木屑、椰壳、玉米穗轴和烟茎;适合的乳化剂和/或起泡剂是:例如非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚,例如,烷芳基聚乙二醇醚,烷基磺酸盐,烷基硫酸盐,芳基磺酸盐以及白蛋白水解产物;适合的分散剂是:例如,木素亚硫酸废液和甲基纤维素。
制剂中可以使用粘合剂如羧甲基纤维素和粉状、颗粒或乳胶形式的天然和合成聚合物,如阿拉伯胶、聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂,如脑磷脂和卵磷脂,和合成磷脂。其它的添加剂可以是矿物油和植物油。
也可以使用着色剂,如无机颜料,例如氧化铁、氧化钛和普鲁士蓝,和有机染料,如茜素染料、偶氮染料和金属酞菁染料,和微量营养元素如铁、锰、硼、铜、钴、钼和锌的盐。
制剂中通常含有按重量计0.1至95%的活性化合物,优选0.5至90%。
为防治杂草,本发明活性化合物,其原样或以其制剂形式,也可以作为与已知除草剂一起的混合物使用,它们可以是终制剂或桶混物。
混合物的可能的共组分是已知除草剂,例如,乙草胺、三氟羧草醚(钠盐)、苯草醚、甲草胺、禾草灭(钠盐)、莠灭净、amidochlor、酰嘧黄隆、莎稗磷、磺草灵、莠去津、azafenidin、四唑嘧黄隆、草除灵、呋草黄、苄嘧黄隆(甲酯)、灭草松、吡草酮、新燕灵(乙酯)、双丙氨膦、甲羧除草醚、双草醚、溴丁酰草胺、溴酚肟、溴苯腈、丁草胺、butroxydim、丁草敌、cafenstrole、caloxydim、双酰草胺、carfentrazone(-ethyl)、甲氧除草醚、灭草畏、氯草敏、氯嘧黄隆(乙酯)、草枯醚、绿黄隆、绿麦隆、环庚草醚、醚黄隆、烯草酮、炔草酸、异噁草松、氯甲酰草胺、二氟吡啶酸、clopyrasulfuron(-methyl)、cloransulam(-methyl)、cumyluron、氰草津、灭草特、环丙嘧磺隆、噻草酮、氰氟草酯、2,4-滴、2,4-滴丁酸、2,4-滴丙酸、甜菜安、燕麦敌、麦草畏、禾草灵、diclosulam、乙酰甲草胺、野燕枯、吡氟酰草胺、diflufenzopyr、唑隆、哌草丹、二甲草胺、二甲丙乙净、二甲吩草胺、dimexyflam、氨氟灵、双苯酰草胺、敌草快、氟硫草定、敌草隆、dymron、epoprodan、茵草敌、戊草丹、乙丁烯氟灵、胺苯黄隆(甲酯)、乙呋草黄、ethoxyfen、ethoxysulfuron、etobenzanid、噁唑禾草灵、麦草伏(异丙酯)、麦草伏(异丙酯-L)、麦草伏(甲酯)、啶嘧黄隆、吡氟禾草灵(丁酯)、唑嘧磺草胺、氟烯草酸、丙炔氟草胺、flumipropyn、flumetsulam、伏草隆、氟咯草隆、乙羧氟草醚(乙酯)、胺草唑、flupropacil、flurpyrsulfuron(-methyl,-sodium)、芴丁酯、氟啶草酮、氯氟吡氧乙酸、氟嘧醇、氟草酮、fluthiacet(-methyl)、fluthiamide、氟黄胺草醚、草铵磷(铵盐)、草甘磷(异丙铵盐)、halosafen、吡氟氯禾灵(乙氧基乙酯)、氟吡甲禾灵、环嗪酮、咪草酯(甲酯)、imazamethapyr、imazamox、咪唑烟酸、咪唑喹啉酸、咪唑乙烟酸、唑吡嘧黄隆、碘苯腈、异丙乐灵、异丙隆、异噁隆、异噁酰草胺、isoxaflutole、异噁草醚、乳氟禾草灵、环草定、利谷隆、2甲4氯、2甲4氯丙酸、苯噻酰草胺、苯嗪草酮、吡唑草胺、甲基苯噻隆、吡喃隆、秀谷隆、异丙甲草胺、磺草唑胺、甲氧隆、甲黄隆(甲酯)、嗪草酮、禾草敌、绿谷隆、萘丙胺、萘氧丙草胺、草不隆、烟嘧黄隆、哒草伏、坪草丹、安磺乐灵、oxadiargyl、噁草酮、oxasulfuron、oxaziclomefone、乙氧氟草醚、百草枯、pelargonicacid、二甲戊灵、pentoxazone、甜草宁、哌草磷、丙草胺、氟嘧黄隆(甲酯)、扑草净、毒草胺、敌稗、噁草酸、异丙草胺、炔苯酰草胺、苄草丹、氟磺隆、pyraflufen(-ethyl)、吡唑特、吡嘧黄隆(乙酯)、苄草唑、pyribenzoxim、稗草丹、哒草特、pyriminobac(-methyl)、嘧草硫醚、二氯喹啉酸、氯甲喹啉酸、灭藻醌、精喹禾灵、喹禾糠酯、砜嘧黄隆、稀禾定、西玛津、西草净、磺草酮、甲磺草胺、甲嘧黄隆、sulfosate、sulfosulfuron、牧草胺、丁噻隆、特丁津、特丁净、噻吩草胺、噻呋酰胺、噻唑烟酸、thidiazimin、噻吩黄隆、禾草丹、仲草丹、tralkoxydim、野麦畏、醚苯黄隆、苯黄隆(甲酯)、绿草定、三氯吡氧乙酸、灭草环、氟乐灵和氟胺黄隆。
也可以是与其它已知活性化合物如杀真菌剂、杀虫剂、杀螨剂、杀线虫剂、驱鸟剂、植物养料和土壤结构改良剂一起的混合物。
活性化合物可以以其本身、以其制剂或由之经进一步稀释而制备的使用形式使用,如直接可用溶液、悬浮液、乳液、粉剂、膏剂和颗粒剂。它们以常规方法使用,例如浇泼、喷雾、弥雾或撒施等等。
本发明活性化合物可以在植物萌发前或后施用。它们也可以在播种前掺入土壤中。
所用的活性化合物的量可以在相当宽的范围内变化。用量基本上取决于所需的效果。通常,使用量在每公顷土表面积用1克至10公斤之间,优选每公顷5克至5公斤。
本发明活性化合物的制备和使用可以参见下列实施例。
制备实施例:
(方法(a))
将2.0g(8mmol)1-氨基-2-氟-4-(2-氯-吡啶-5-基-甲氧基)-苯、1.2g(8mmol)邻苯二甲酸酐和50ml乙酸的混合物加热回流5小时,之后在室温下搅拌18小时,随后再加热回流4小时。之后混合物在水泵真空下浓缩,残余物用水/乙酸乙酯震荡,分离出有机相,用水洗涤,用硫酸钠干燥并过滤。滤液在水泵真空下浓缩,残余物用二异丙基醚消化,晶体产物通过抽吸过滤分离。
由此给出1.9g(理论值的62%)N-(2-氟-(2-氯-吡啶-5-基-甲氧基)-苯基]-邻苯二甲酰亚胺,熔点183℃。
(方法(b))
将0.90g(3.3mmol)4-(2-氟-4-羟基-苯基)-2-二氟甲基-1-甲基-1,2,4-三唑啉-3,5-二酮、0.65g(3.3mmol)2-氯-5-氯甲基-吡啶、0.55g碳酸钾和10ml N,N-二甲基-甲酰胺的混合物在80℃下搅拌3小时。在稍微冷却后,将此混合物倒入预先与冰混合的1N盐酸和乙醚的溶剂混合物中。在充分搅拌之后,晶体产物通过抽吸过滤分离。
由此给出0.35g(理论值的26.5%)4-[2-氟-4-(2-氯-吡啶基-5-基甲氧基)-苯基]-2-二氟甲基-1-甲基-1,2,4-三唑啉-3,5-二酮,熔点134℃。
将0.56g(14mmol)60%氢化钠的矿物油液加入到2.3g(15mmol)2-氯-5-羟基甲基-吡啶的20ml乙腈溶液中。混合物在室温(大约20℃)下搅拌15分钟,之后与3.4g(10mmol)4-氯-3-(2,4-二氟-5-硝基-苯基)-1-甲基-5-三氟甲基-1H-吡唑混合,开在室温下搅拌4小时。之后将此混合物用大约等量的水和乙酸乙酯稀释至大约三倍体积,并用2N盐酸酸化。分离出有机相,用饱和碳酸氢钠水溶液和用饱和氯化钠水溶液洗涤,用硫酸钠干燥并过滤。在水泵真空下仔细将溶剂从滤液中蒸馏掉。
由此给出4.6g(理论值的99%)4-氯-3-[4-[(2-氯-吡啶-5-基)-甲氧基]-2-氟-5-硝基-苯基]-1-甲基-5-三氟甲基-1H-吡唑,熔点170℃。
表1中的实例7化合物可以例如如下制备:
在80-90℃下,将27g(58mmol)4-氯-3-[4-[(2-氯-吡啶-5-基)-甲氧基]-2-氟-5-硝基-苯基]-1-甲基-5-三氟甲基-1H-吡唑在120ml乙酸和60ml乙酸乙酯的悬浮液缓慢计量入32.3g(0.58mol)铁(粉)和72ml浓度5%的乙酸水溶液中。反应混合物在室温(大约20℃)下搅拌150分钟,之后滤过Celite(以Kieselguhr为基础的过滤器辅剂)。过滤残余物用水和乙酸乙酯洗涤,之后分离有机相并合并在一起,用饱和碳酸氢钠和饱和氯化钠水溶液洗涤,用硫酸钠干燥并过滤。在水泵真空下仔细将溶剂从滤液中蒸馏掉。
由此给出24.8g(理论值的98%)4-氯-3-[5-氨基-4-[(2-氯-吡啶-5-基)-甲氧基]-2-氟-苯基]-1-甲基-5-三氟甲基-1H-吡唑,熔点116℃。
表1中的实例4化合物可以例如如下制备:
将2.8g(6.4mmol)4-氯-3-[5-氨基-4-[(2-氯-吡啶-5-基)-甲氧基]-2-氟-苯基]-1-甲基一5-三氟甲基-1H-吡唑的20ml四氢呋喃溶液加热回流,同时逐滴加入1.7ml(12.8mmol)亚硝酸正戊酯。完成的反应混合物再加热回流30分钟,之后在水泵真空下浓缩。油性残余物通过柱色谱(硅胶,二氯甲烷/甲醇,体积比100∶1)纯化。
由此给出0.65g(理论值的24%)4-氯-3-[4-[(2-氯-吡啶-5-基)-甲氧基]-2-氟-苯基]-1-甲基-5-三氟甲基-1H-吡唑,熔点73℃。式(Ⅱ)起始原料
将8.65g(55mmol)3-氟-4-硝基-苯酚、9.72g(60mmol)2-氯-5-氯乙基-吡啶、8.3g(60mmol)碳酸钾和150ml丁酮的混合物在80℃下搅拌10小时,之后在水泵真空下浓缩。残余物用2N盐酸水溶液、乙酸乙酯和乙醚的溶剂混合物搅拌,之后,晶体产物通过抽滤分离。
由此给出9.8g(理论值的63%)2-氯-5-(3-氟-4-硝基-苯氧基甲基)-吡啶,熔点174℃。步骤2
先将9.5g(33.6mmol)2-氯-5-(3-氟-4-硝基-苯氧基甲基)-吡啶加入150ml乙酸和10ml水的混合物中,之后将混合物加热至50℃。再一次一点地将9.5g铁粉加入,并将此混合物在20℃至25℃间搅拌60分钟,并过滤。滤液浓缩,残余物用水/乙酸乙酯振荡,并将有机相用水洗涤,用硫酸钠干燥并过滤。滤液在水泵真空下浓缩,残余物用石油醚消化,晶体产物通过抽滤分离。
由此给出7.3g(理论值的86%)2-氯-5-(4-氨基-3-氯-苯氧基甲基)-吡啶,熔点101℃。
式(Ⅲ)起始原料
实施例(Ⅲ-1)步骤1
先将15.0g(106.4mmol)1-氨基-2-氟-4-甲氧基-苯加入到400ml乙酸乙酯中,并在室温下,在搅拌下逐滴与47g氯甲酸三氯甲基酯(双光气)混合。之后将混合物加热回流2小时,随后在水泵真空下浓缩。残余物用200ml乙腈消化,与23g 2-甲基-1-乙氧基羰基-肼和9.8g碳酸氢钠混合。此混合物加热回流6小时,随后在水泵真空下浓缩。残余物与1N盐酸和乙醚的混合物混合,晶体产物通过抽滤分离。
由此给出21.5g(理论值的71%)4-(2-氟-4-甲氧基-苯基)-1-乙氧基羰基-2-甲基-氨基脲。
1H-NMR(DMSO-D6,δ,ppm):2.98(N-CH3)。
步骤2
将21.0g(83.7mmol)4-(2-氟-4-甲氧基-苯基)-1-乙氧基羰基-2-甲基-氨基脲和210ml 4N氢氧化钠水溶液在80℃下加热20分钟,之后冷却至10℃,随后与70ml浓盐酸混合。之后混合物与二氯甲烷一起振荡,有机相用水洗涤,用硫酸钠干燥并过滤。滤液在水泵真空下浓缩,残余物用乙醚消化,晶体产物通过抽滤分离。
由此给出13.9g(理论值的79%)4-(2-氟-4-甲氧基-苯基)-1-甲基-1,2,3-三唑啉-3,5-二酮。
1H-NMR(DMSO-D6,δ,ppm):3.81(N-CH3)。
将一氯二氟甲烷通入到加热到100℃的14.0g(58.6mmol)4-(2-氟-4-甲氧基-苯基)-1-甲基-1,2,3-三唑啉-3,5-二酮、8.5g碳酸钾和50ml N,N-二甲基甲酰胺的混合物中三小时。在稍微冷却后,将此混合物倒入冰水中,用2N盐酸酸化,并与乙酸乙酯一起振荡。分离出有机相,用水洗涤,用硫酸钠干燥并过滤。滤液在水泵真空下浓缩,残余物通过柱色谱(硅胶,乙酸乙酯/己烷,体积比1∶2)分离。
由此给出(作为第二级分)4.0g(理论值的24%)4-(2-氟-4-甲氧基-苯基)-2-二氟甲基-1-甲基-1,2,3-三唑啉-3,5-二酮,熔点88℃。
将2.0g(6.9mmol)4-(2-氟-4-甲氧基-苯基)-2-二氟甲基-1-甲基-1,2,3-三唑啉-3,5-二酮溶解于30ml二氯甲烷中,并将此混合物逐滴加入到3g三氟化硼的30ml二氯甲烷溶液中。此反应混合物在室温下搅拌6小时。在加毕50ml水后,分离出有机相,用水洗涤,用硫酸钠干燥并过滤。在水泵真空下仔细将溶液从滤液中蒸馏掉。
由此给出1.6g(理论值的84%)4-(2-氟-4-羟基-苯基)-2-二氟甲基-1-甲基-1,2,3-三唑啉-3,5-二酮,熔点141℃。
应用实施例
实施例A
芽前试验
溶剂: 5份重量丙酮
乳化剂: 1份重量的烷芳基聚乙二醇醚
制备适合的活性化合物制剂时,将1份重量的活性化合物与所述量的溶剂混合,将所述量的乳化剂加入,并用水将此乳油稀释至所需浓度。
将试验植物的种子播入通常的土壤中,约24小时后,土壤用活性化合物制剂浇水,在每单位面积上施用特定量的活性成分。选择喷雾液的浓度,使所需的活性化合物的特定量以1000升水/公顷的喷雾量施用。
三周后,将植物的损害程度与未处理对照的发育相比较,目测定出损害%。
数值的含义如下:
0%=无作用(与未处理相同)
100%=完全损害
在此试验中,例如,制备实施例1、2、3和4对杂草显示出强活性,且它们的一些能被作物如玉米和小麦很好地耐受。
实施例B
芽后试验
溶剂: 5份重量丙酮
乳化剂: 1份重量的烷芳基聚乙二醇醚
制备适合的活性化合物制剂时,将1份重量的活性化合物与所述量的溶剂混合,将所述量的乳化剂加入,并用水将此乳油稀释至所需浓度。
向株高5-15厘米的试验植物按单位面积喷雾施用一定量的所需活性化合物制剂。选择喷雾液的浓度,使所需化合物的特定量以1,000升水/公顷的量施用。
三周后,将植物的损害程度与未处理对照相比较,定出损害%。
数值的含义如下:
0%=无作用(与未处理相同)
100%=完全破坏
在此试验中,制备实施例2、3、4和5对杂草显示出强活性,且它们的一些能被作物如小麦很好地耐受。
Claims (8)
酰基、硫代氨基甲酰基、卤素,或代表均可任选由氰基-、卤素-或
烷氧基取代的烷基、烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、
烷基氨基、二烷基氨基、烷基羰基、烷氧基羰基、烷基羰基氨基、
烷氧基羰基氨基或烷基磺酰基氨基,X2 代表氢或卤素,Z1 代表任选取代的选自下列的杂芳基:呋喃基、苯并呋喃基、吡咯基、
吡唑基、咪唑基、三唑基、噁唑基、异噁唑基、苯并噁唑基、噻唑
基、异噻唑基、苯并噻唑基、苯并咪唑基、吡啶基、喹啉基、异喹
啉基、嘧啶基、吡嗪基、哒嗪基、喹唑啉基或喹喔啉基,和Z2 代表下列基团之一其中Q 代表O或S,R1 代表氢、氰基、卤素,或代表均可任选由氰基-、卤素-或烷氧基-
取代的烷基、烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷基
氨基、二烷基氨基、链烯基、链烯氧基、链烯硫基、链烯氨基、炔
基、炔氧基、炔硫基、环烷基、环烷基氧基、环烷基硫基或环烷基
氨基,或任选与相邻的R1一起代表烷二基(亚烷基),和R2 代表氢、氰基、甲酰基,或代表均可任选由氰基-、卤素-或烷氧基
-取代的烷基、烷基羰基、烷氧基羰基、链烯基或炔基。
2.权利要求1的取代的杂芳基甲基化合物,其特征在于Q 代表O、S、SO或SO2,X1 代表氢、羟基、巯基、氨基、硝基、甲酰基、羧基、氰基、氨基甲
酰基、硫代氨基甲酰基、卤素,或任选由氰基-、卤素-或C1-C4-烷
氧基-取代的各在烷基中具有1至6个碳原子的烷基、烷氧基、烷
硫基、烷基亚磺酰基、烷基磺酰基、烷基氨基、二烷基氨基、烷基
羰基、烷氧基羰基、烷基羰基氨基、烷氧基羰基氨基或烷基磺酰基
氨基,X2 代表氢或卤素,Z1 代表任选取代的选自下列的杂芳基:呋喃基、苯并呋喃基、吡咯基、
吡唑基、咪唑基、三唑基、噁唑基、异噁唑基、苯并噁唑基、噻唑
基、异噻唑基、苯并噻唑基、苯并咪唑基、吡啶基、喹啉基、异喹
啉基、嘧啶基、吡嗪基、哒嗪基、喹唑啉基或喹喔啉基,其中可能
的取代基优选选自下列:
硝基、氨基、羟基、羧基、氰基、氨基甲酰基、硫代氨基甲酰基、
磺基、氯代磺酰基、氨基磺酰基、卤素,均可任选由氰基-、卤素-
或C1-C4-烷氧基-取代的各在烷基部分具有1至4个碳原子的烷基、
烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷基氨基、烷基羰
基、烷氧基羰基、烷基氨基羰基、烷基羰基氨基、烷氧基羰基氨基
或烷基磺酰基氨基,或苯基,
和Z2 代表下列基团之一:其中Q1 代表O或S,R1 代表氢、氰基、卤素,代表均可任选由氰基-、卤素-或C1-C4-烷氧
基-取代的在烷基部分各具有1至6个碳原子的烷基、烷氧基、烷
硫基、烷基亚磺酰基、烷基磺酰基、烷基氨基或二烷基氨基,代表
均可任选由卤素取代的各在链烯基或炔基部分具有2至6个碳原子
的链烯基、链烯氧基、链烯硫基、链烯基氨基、炔基、炔氧基或炔
硫基,代表均可任选由氰基-、卤素-或C1-C4-烷氧基-取代的各在
环烷基中具有3至6个碳原子的环烷基、环烷基氧基、环烷基硫基
或环烷基氨基,或任选与相邻的R1一起代表具有3至5个碳原子的
烷二基(亚烷基),和R2 代表氢、氰基、甲酰基,代表均可任选由氰基-、卤素-或C1-C4-烷
氧基-取代的各在烷基中具有1至6个碳原子的烷基、烷基羰基、
烷氧基羰基,或代表均可任选由卤素取代的各具有3至6个碳原子
的链烯基或炔基。
3.权利要求1的取代的杂芳基甲基化合物,其特征在于,Q 代表O、S、SO或SO2,X1 代表氢、羟基、巯基、氨基、硝基、甲酰基、羧基、氰基、氨基甲
酰基、硫代氨基甲酰基、氟、氯、溴,代表均可任选由氰基-、氟-、
氯-、甲氧基-或乙氧基-取代的甲基、乙基、正或异丙基、甲氧基、
乙氧基、正或异丙氧基、甲硫基、乙硫基、正或异丙硫基、甲基亚
磺酰基、乙基亚磺酰基、甲基磺酰基、乙基磺酰基、甲基氨基、乙
基氨基、正或异丙基氨基、二甲基氨基、二乙基氨基、乙酰基、丙
酰基、甲氧基羰基、乙氧基羰基、乙酰基氨基、丙酰基氨基、甲氧
基羰基氨基、乙氧基羰基氨基、甲基磺酰基氨基、乙基磺酰基氨基、
正或异丙基磺酰基氨基,X2 代表氢、氟、氯或溴,Z1 代表任选取代的选自下列的杂芳基:呋喃基、苯并呋喃基、吡咯基、
吡唑基、咪唑基、三唑基、噁唑基、异噁唑基、苯并噁唑基、噻唑
基、异噻唑基、苯并噻唑基、苯并咪唑基、吡啶基、喹啉基、异喹
啉基、嘧啶基、吡嗪基、哒嗪基、喹唑啉基或喹喔啉基,其中可能
的取代基优选选自下列:
硝基、氨基、羟基、羧基、氰基、氨基甲酰基、硫代氨基甲酰基、
氨基磺酰基、氟、氯、溴,均可任选由氰基-、氟-、氯-、甲氧基-
或乙氧基-取代的甲基、乙基、正或异丙基、正-、异-、仲-或叔丁
基、甲氧基、乙氧基、正或异丙氧基、正-、异-、仲-或叔丁氧基、
甲硫基、乙硫基、正或异丙硫基、正-、异-、仲-或叔丁硫基、甲
基亚磺酰基、乙基亚磺酰基、甲基磺酰基、乙基磺酰基、甲基氨基、
乙基氨基、正或异丙基氨基、正-、异-、仲-或叔丁基氨基、乙酰
基、丙酰基、正或异丁酰基、甲氧基羰基、乙氧基羰基、正或异丙
氧基羰基、甲基氨基羰基、乙基氨基羰基、正或异丙基氨基羰基、
乙酰基氨基、丙酰基氨基、正-或异丁酰基氨基、甲氧基羰基氨基、
乙氧基羰基氨基、正或异丙氧基羰基氨基、甲基磺酰基氨基、乙基
磺酰基氨基、正或异丙基磺酰基氨基、正-、异-、仲-或叔丁基磺
酰基氨基,或苯基,和Z2 代表下列基团之一其中Q1 代表O或S,R1 代表氢、氰基、氟、氯、溴,或代表均可任选由氰基-、氟-、氯-、
甲氧基-或乙氧基-取代的甲基、乙基、正或异丙基、甲氧基、乙氧
基、正或异丙氧基、甲硫基、乙硫基、正或异丙硫基、甲基亚磺酰
基、乙基亚磺酰基、甲基磺酰基、乙基磺酰基、甲基氨基、乙基氨
基、正或异丙基氨基、二甲基氨基、二乙基氨基,代表均可任选由
氟-、氯-或溴-取代的乙烯基、丙烯基、丙烯基氧基、丙烯基硫基、
丙烯基氨基、乙炔基、丙炔基、丙炔基氧基或丙炔基硫基,或代表
均可任选由氰基-、氟-、氯-、甲基-、乙基-、正-或异丙基-取代
的环丙基、环丁基、环戊基、环己基、环丙基氧基、环丁基氧基、
环戊基氧基、环己基氧基、环丙基氨基、环丁基氨基、环戊基氨基
或环己基氨基,或任选与相邻R1一起代表丙-1,3-二基(三亚甲基)
或丁-1,4-二基(四亚甲基),和R2 代表氢、氰基、甲酰基,代表均可任选由氰基-、氟-、氯-、甲氧
基-或乙氧基-取代的甲基、乙基、正或异丙基、乙酰基、丙酰基、
正或异丁酰基、甲氧基羰基、乙氧基羰基、正或异丙氧基羰基,或
代表均可任选由氟-、氯-或溴-取代的丙烯基、丁烯基、丙炔基或
丁炔基。
4.权利要求1至3之一的取代的杂芳基甲基化合物,其特征在于,Z2代表下式的杂环基,而Q、X1、X2以及Z1和R2如权利要求1至3之一中所定义:
6.制备权利要求1至3之一的取代的杂芳基甲基化合物的方法,其特征在于,(a)如果适合在稀释剂存在下和如果适合在反应辅助剂存在下,
使邻苯二甲酸酐或3,4,5,6-四氢-邻苯二甲酸酐与通式(Ⅱ)的氨基苯衍生物反应
其中
Q、X1、X2和Z1如权利要求1至3之一中所定义,
或(b)如果适合在稀释剂存在下和如果适合在反应辅助剂存在下,
其中
Q、X1、X2和Z2如权利要求1至3之一中所定义,
与通式(Ⅳ)的杂芳基甲基卤反应
X3-CH2-Z1 (Ⅳ)
其中
Z1如上所定义,和
X3代表卤素,
或(c)如果适合在反应辅助剂存在下和在如果适合在稀释剂存在下,
其中
X1、X2和Z2如权利要求1至3之一中所定义,和
X4代表卤素,
与通式(Ⅵ)的杂芳烃反应,
HQ-CH2-Z1 (Ⅵ)
其中
Q和Z1如权利要求1至3之一中所定义,
如果适合,随后用常规方式在取代基定义的范围内进行亲电或亲核取代反应和/或氧化反应或还原反应。
7.权利要求1至5之一的至少一种取代的杂芳基甲基化合物防治不想要的植物的应用。
8.除草组合物,其特征在于,包含至少一种权利要求1至5之一的取代的杂芳基甲基化合物和常规的增充剂。
Applications Claiming Priority (2)
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DE19803395A DE19803395A1 (de) | 1998-01-29 | 1998-01-29 | Substituierte Heteroarylmethylverbindungen |
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CN1289330A true CN1289330A (zh) | 2001-03-28 |
Family
ID=7856003
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EP (1) | EP1051414A1 (zh) |
JP (1) | JP2002501917A (zh) |
KR (1) | KR20010033804A (zh) |
CN (1) | CN1289330A (zh) |
AU (1) | AU2421599A (zh) |
BR (1) | BR9908341A (zh) |
CA (1) | CA2319053A1 (zh) |
DE (1) | DE19803395A1 (zh) |
WO (1) | WO1999038861A1 (zh) |
Cited By (2)
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CN105517995A (zh) * | 2013-07-08 | 2016-04-20 | 拜耳作物科学股份公司 | 作为杀虫剂的六元c-n键合的芳基硫化物和芳基硫氧化物衍生物 |
CN111187213A (zh) * | 2018-11-15 | 2020-05-22 | 华中师范大学 | 多卤代5-(2-羟基苯基)吡唑类化合物及其制备方法和应用 |
Families Citing this family (1)
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IT1313601B1 (it) | 1999-08-05 | 2002-09-09 | Isagro Ricerca Srl | Fenilpirazoli ad attivita' erbicida |
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US4332944A (en) * | 1981-07-09 | 1982-06-01 | Zoecon Corporation | Compositions and use |
AU649474B2 (en) * | 1990-08-06 | 1994-05-26 | Monsanto Company | Herbicidal substituted aryl alkylsulfonyl pyrazoles |
DE19728125A1 (de) * | 1997-07-02 | 1999-01-07 | Bayer Ag | Substituierte Aryluracile |
-
1998
- 1998-01-29 DE DE19803395A patent/DE19803395A1/de not_active Withdrawn
-
1999
- 1999-01-16 CA CA002319053A patent/CA2319053A1/en not_active Abandoned
- 1999-01-16 KR KR1020007007356A patent/KR20010033804A/ko not_active Application Discontinuation
- 1999-01-16 BR BR9908341-8A patent/BR9908341A/pt not_active Application Discontinuation
- 1999-01-16 EP EP99903637A patent/EP1051414A1/de not_active Withdrawn
- 1999-01-16 WO PCT/EP1999/000238 patent/WO1999038861A1/de not_active Application Discontinuation
- 1999-01-16 CN CN99802547A patent/CN1289330A/zh active Pending
- 1999-01-16 AU AU24215/99A patent/AU2421599A/en not_active Abandoned
- 1999-01-16 JP JP2000529329A patent/JP2002501917A/ja active Pending
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105517995A (zh) * | 2013-07-08 | 2016-04-20 | 拜耳作物科学股份公司 | 作为杀虫剂的六元c-n键合的芳基硫化物和芳基硫氧化物衍生物 |
CN105517995B (zh) * | 2013-07-08 | 2018-10-02 | 拜耳作物科学股份公司 | 作为农药的六元c-n键合的芳基硫化物和芳基硫氧化物衍生物 |
CN111187213A (zh) * | 2018-11-15 | 2020-05-22 | 华中师范大学 | 多卤代5-(2-羟基苯基)吡唑类化合物及其制备方法和应用 |
CN111187213B (zh) * | 2018-11-15 | 2021-09-07 | 华中师范大学 | 多卤代5-(2-羟基苯基)吡唑类化合物及其制备方法和应用 |
Also Published As
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CA2319053A1 (en) | 1999-08-05 |
WO1999038861A1 (de) | 1999-08-05 |
AU2421599A (en) | 1999-08-16 |
JP2002501917A (ja) | 2002-01-22 |
DE19803395A1 (de) | 1999-08-05 |
EP1051414A1 (de) | 2000-11-15 |
BR9908341A (pt) | 2001-10-02 |
KR20010033804A (ko) | 2001-04-25 |
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