CN1108293C - 取代的1-氨基-3-苯基-尿嘧啶衍生物、其制备及其作为除草剂的应用 - Google Patents
取代的1-氨基-3-苯基-尿嘧啶衍生物、其制备及其作为除草剂的应用 Download PDFInfo
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- CN1108293C CN1108293C CN96196722A CN96196722A CN1108293C CN 1108293 C CN1108293 C CN 1108293C CN 96196722 A CN96196722 A CN 96196722A CN 96196722 A CN96196722 A CN 96196722A CN 1108293 C CN1108293 C CN 1108293C
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- 239000004009 herbicide Substances 0.000 title abstract description 6
- 238000002360 preparation method Methods 0.000 title description 25
- YSYCHVGDGZZWBB-UHFFFAOYSA-N 1-amino-3-phenylpyrimidine-2,4-dione Chemical class O=C1N(N)C=CC(=O)N1C1=CC=CC=C1 YSYCHVGDGZZWBB-UHFFFAOYSA-N 0.000 title 1
- -1 thiocarbamoyl Chemical group 0.000 claims abstract description 325
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 30
- 239000001257 hydrogen Substances 0.000 claims abstract description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 18
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 9
- 239000000460 chlorine Substances 0.000 claims description 36
- 229910052801 chlorine Inorganic materials 0.000 claims description 36
- 239000011737 fluorine Substances 0.000 claims description 32
- 229910052731 fluorine Inorganic materials 0.000 claims description 32
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 23
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 21
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
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- 238000006243 chemical reaction Methods 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
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- BISHACNKZIBDFM-UHFFFAOYSA-N 5-amino-1h-pyrimidine-2,4-dione Chemical class NC1=CNC(=O)NC1=O BISHACNKZIBDFM-UHFFFAOYSA-N 0.000 claims description 8
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
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- 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 5
- 125000006638 cyclopentyl carbonyl group Chemical group 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
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- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
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- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 claims description 3
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- OWOHLURDBZHNGG-YFKPBYRVSA-N (8ar)-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione Chemical group O=C1CNC(=O)[C@@H]2CCCN12 OWOHLURDBZHNGG-YFKPBYRVSA-N 0.000 claims description 2
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- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims description 2
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- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 2
- 125000006337 tetrafluoro ethyl group Chemical group 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
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
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- 239000004094 surface-active agent Substances 0.000 claims 1
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- 150000001875 compounds Chemical class 0.000 abstract description 38
- 125000000217 alkyl group Chemical group 0.000 abstract description 17
- 125000003342 alkenyl group Chemical group 0.000 abstract description 15
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract description 10
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract description 8
- 125000005129 aryl carbonyl group Chemical group 0.000 abstract description 8
- 125000005090 alkenylcarbonyl group Chemical group 0.000 abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 6
- 229910052736 halogen Inorganic materials 0.000 abstract description 6
- 150000002367 halogens Chemical class 0.000 abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 abstract description 3
- 125000006193 alkinyl group Chemical group 0.000 abstract 4
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 abstract 2
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 abstract 2
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 abstract 2
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 125000000304 alkynyl group Chemical group 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
- 239000002994 raw material Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 6
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
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- 239000013543 active substance Substances 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
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- 235000010755 mineral Nutrition 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
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- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 241000209149 Zea Species 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 125000005087 alkynylcarbonyl group Chemical group 0.000 description 4
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- 239000013068 control sample Substances 0.000 description 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 4
- 230000001419 dependent effect Effects 0.000 description 4
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
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- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 4
- WCFAPJDPAPDDAQ-UHFFFAOYSA-N 1,2-dihydropyrimidine Chemical compound C1NC=CC=N1 WCFAPJDPAPDDAQ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
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- 239000000047 product Substances 0.000 description 1
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 1
- VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-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
- BACHBFVBHLGWSL-JTQLQIEISA-N rac-diclofop methyl Natural products C1=CC(O[C@@H](C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-JTQLQIEISA-N 0.000 description 1
- 239000011541 reaction mixture Substances 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
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical group 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
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 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
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000003516 soil conditioner Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-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
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
- HVZJRWJGKQPSFL-UHFFFAOYSA-N tert-Amyl methyl ether Chemical compound CCC(C)(C)OC HVZJRWJGKQPSFL-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
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 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
- 150000003918 triazines Chemical class 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
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 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
- 150000003672 ureas Chemical class 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000003643 water by type Substances 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
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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- 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
- C07D401/10—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 carbon chain containing aromatic rings
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- 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
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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Abstract
本发明涉及通式(I)的取代氨基尿嘧啶,其中R1是氢、氰基或卤素,R2是氰基或硫代氨基甲酰基,R3是氢或选自下列的任选取代的基团:烷基、烷基羰基、链烯基、链烯基羰基、炔基、炔基羰基、环烷基、环烷基羰基、环烷基烷基、环烷基烷基羰基、芳基羰基、芳烷基羰基和杂环基羰基,R4是氢或选自下列的任选取代的基团:烷基、烷基羰基、链烯基、链烯基羰基、炔基、炔基羰基、环烷基、环烷基羰基、环烷基烷基、环烷基烷基羰基、芳基羰基、芳烷基羰基和杂环基羰基,或与R3一起形成任选取代的烷二基、氧代烷二基或二氧代烷二基,R5是氢、卤素或任选取代的烷基或烷氧基,R6是任选取代的烷基,R7是氢或选自下列的任选取代的基团:烷基、链烯基和炔基,且R8是氢或选自下列的任选取代的基团:烷基、链烯基和炔基。本发明还涉及制备这些化合物的方法及其作为除草剂的应用。
Description
本发明涉及新的取代氨基尿嘧啶类化合物、其制备方法及其作为除草剂的应用。
已知某些取代的尿嘧啶具有除草性能(参见EP 408 382/US 5 084084/US 5 127 935/US 5 154 755/EP 563 384/EP 648 749/WO 91/00278/US4 979 982/US 5 169 430)。然而,这些化合物不是特别重要的。
其中
R1代表氢、氰基或卤素,
R2代表氰基或硫代氨基甲酰基,
R3代表氢或代表选自下列的各任选取代的基团:烷基、烷基羰基、链烯基、链烯基羰基、炔基、炔基羰基、环烷基、环烷基羰基、环烷基烷基、环烷基烷基羰基、芳基羰基、芳烷基羰基或杂环基羰基,
R4代表氢或代表选自下列的各任选取代的基团:烷基、烷基羰基、链烯基、链烯基羰基、炔基、炔基羰基、环烷基、环烷基羰基、环烷基烷基、环烷基烷基羰基、芳基羰基、芳烷基羰基或杂环基羰基,或与R3一起代表各任选取代的烷二基、氧代烷二基或二氧代烷二基,
R5代表氢、卤素或代表各任选取代的烷基或烷氧基,
R6代表任选取代的烷基,
R7代表氢或代表选自下列的各任选取代的基团:烷基、链烯基或炔基,且
R8代表氢或代表选自下列的各任选取代的基团:烷基、链烯基或炔基。
新的通式(I)的取代氨基苯基尿嘧啶类化合物是如下获得的:
如果需要在反应助剂存在下,且如果需要在稀释剂存在下,使通式(II)氨基尿嘧啶类化合物与通式(III)、(IV)、(V)或(VI)的烷基化或酰基化试剂反应,
其中
R1、R2、R5、R6、R7和R8各如上所定义,且
Z代表任选取代的烷基磺酰基氨基或基团-NR3R4,其中R3和R4各如上所定义,
X-R3 (III) R3-CO-O-CO-R3 (IV)
X-R4 (V) R4-CO-O-CO-R4 (VI)
其中
R3和R4各如上所定义。
通过常规的方法,例如用乙酸铵/冰乙酸去酰基化( )或通过加硫化氢( ),可以将通式(I)化合物转化成根据上面定义的其它通式(I)化合物。
新的通式(I)的取代氨基尿嘧啶类化合物具有强的除草性能。
在定义中,饱和或不饱和的烃链如烷基、链烯基或炔基各是直链或支链。
卤素通常代表氟、氯、溴或碘,优选氟、氯或溴,特别是氟或氯。
本发明优选提供式(I)化合物,其中
R1代表氢、氰基、氟或氯,
R2代表氰基或硫代氨基甲酰基,
R3代表氢或代表各任选由氰基-、羧基-、氟-、氯-、溴-、C1-C4-烷氧基-、C1-C4-烷基羰基-或C1-C4-烷氧基羰基取代的烷基、烷基羰基、链烯基、链烯基羰基、炔基或炔基羰基,它们各在烷基、链烯基或炔基部分具有至多10个碳原子,
R3还代表各任选由氰基-、羧基-、氟-、氯-、溴-、C1-C4-烷基-、C1-C4-烷氧基-、C1-C4-烷基羰基-或C1-C4-烷氧基羰基取代的环烷基、环烷基羰基、环烷基烷基或环烷基烷基羰基,它们各在环烷基部分具有3至8个碳原子和任选在烷基部分具有至多4个碳原子,
R3还代表在芳基部分具有6或10个碳原子和任选在烷基部分具有至多4个碳原子的芳基羰基或芳烷基羰基,该芳基羰基或芳烷基羰基基团各任选由氰基、羧基、硝基、氨基甲酰基、硫代氨基甲酰基、氟、氯、溴,由C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-烷基亚磺酰基、C1-C4-烷基磺酰基、C1-C4-烷基-羰基或C1-C4-烷氧基羰基(它们各任选由氟和/或氯取代),由苯基、苯氧基或苯硫基(它们各任选由氟、氯、溴、氰基、甲基、甲氧基、三氟甲基和/或三氟甲氧基取代)取代,
R3还代表取代的呋喃基羰基、四氢呋喃基羰基、噻吩基羰基、四氢噻吩基羰基、噁唑基羰基、异噁唑基羰基、噻唑基羰基、噁二唑基羰基、噻二唑基羰基、吡唑基羰基、吡啶基羰基或嘧啶基羰基,它们各任选由氰基、羧基、氨基甲酰基、硫代氨基甲酰基、氟、氯、溴,由C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-烷基亚磺酰基、C1-C4-烷基磺酰基、C1-C4-烷基-羰基或C1-C4-烷氧基羰基(它们各任选由氟和/或氯取代),由苯基、苯氧基或苯硫基(它们各任选由氟、氯、溴、氰基、甲基、甲氧基、三氟甲基和/或三氟甲氧基取代)取代,
R4代表氢或代表各任选由氰基-、羧基-、氟-、氯-、溴-、C1-C4-烷氧基-、C1-C4-烷基羰基-或C1-C4-烷氧基羰基取代的烷基、烷基羰基、链烯基、链烯基羰基、炔基或炔基羰基,它们各在烷基、链烯基或炔基部分具有至多10个碳原子,
R4还代表各任选由氰基-、羧基-、氟-、氯-、溴-、C1-C4-烷基-、C1-C4-烷氧基-、C1-C4-烷基羰基-或C1-C4-烷氧基羰基取代的环烷基、环烷基羰基、环烷基烷基或环烷基烷基羰基,它们各在环烷基部分具有3至8个碳原子和任选在烷基部分具有至多4个碳原子,
R4还代表在芳基部分具有6或10个碳原子和任选在烷基部分具有至多4个碳原子的芳基羰基或芳烷基羰基,该芳基羰基或芳烷基羰基基团各任选由氰基、羧基、硝基、氨基甲酰基、硫代氨基甲酰基、氟、氯、溴,由C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-烷基亚磺酰基、C1-C4-烷基磺酰基、C1-C4-烷基-羰基或C1-C4-烷氧基羰基(它们各任选由氟和/或氯取代),由苯基、苯氧基或苯硫基(它们各任选由氟、氯、溴、氰基、甲基、甲氧基、三氟甲基和/或三氟甲氧基取代)取代,
R4还代表呋喃基羰基、四氢呋喃基羰基、噻吩基羰基、四氢噻吩基羰基、噁唑基羰基、异噁唑基羰基、噻唑基羰基、噁二唑基羰基、噻二唑基羰基、吡唑基羰基、吡啶基羰基或嘧啶基羰基,它们各任选由氰基、羧基、氨基甲酰基、硫代氨基甲酰基、氟、氯、溴,由C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-烷基亚磺酰基、C1-C4-烷基磺酰基、C1-C4-烷基-羰基或C1-C4-烷氧基羰基(它们各任选由氟和/或氯取代),由苯基、苯氧基或苯硫基(它们各任选由氟、氯、溴、氰基、甲基、甲氧基、三氟甲基和/或三氟甲氧基取代)取代,
R4与R3一起代表各任选由氟-、氯-、溴-、C1-C4-烷基-或C1-C4-卤代烷基-取代的各具有至多6个碳原子的烷二基、氧代烷二基或二氧代烷二基,
R5代表氢、氟、氯溴或代表各任选由氟-和/或氯-取代的各具有1至4个碳原子的烷基或烷氧基,
R6代表任选由氟-和/或氯-取代的具有1至4个碳原子的烷基,
R7代表氢或代表各任选由氟-、氯-或C1-C4-烷氧基-取代的各具有至多6个碳原子的烷基、链烯基和炔基,且
R8代表氢或代表各由任选氟-、氯-或C1-C4-烷氧基-取代的各具有至多6个碳原子的烷基、链烯基和炔基。
本发明特别提供式(I)化合物,其中
R1代表氢、氟或氯,
R2代表氰基或硫代氨基甲酰基,
R3代表氢或代表各任选由氰基-、羧基-、氟-、氯-、甲氧基-、乙氧基-、正或异丙氧基-、乙酰基-、丙酰基-、甲氧基羰基-、乙氧基羰基-、正或异丙氧基羰基取代的甲基、乙基、正或异丙基、正-、异-、仲-或叔丁基、正-、异-、仲-或叔戊基、乙酰基、正或异丙基羰基、正-、异-、仲-或叔丁基羰基、丙烯基、丙烯基羰基、丁烯基、丁烯基羰基、戊烯基、戊烯基羰基、丙炔基、丙炔基羰基、丁炔基、丁炔基羰基、戊炔基或戊炔基羰基,
R3还代表各任选由氰基-、羧基-、氟-、氯-、溴-、甲基-、乙基-、正或异丙基-、甲氧基-、乙氧基-、正或异丙氧基-、乙酰基-或丙酰基-、甲氧基羰基-、乙氧基羰基-、正或异丙氧基羰基-取代的环丙基、环丙基羰基、环丁基、环丁基羰基、环戊基、环戊基羰基、环己基、环己基羰基、环丙基甲基、环丁基甲基、环戊基甲基或环己基甲基,
R3还代表各任选由氰基-、羧基-、硝基-、氨基甲酰基-、硫代氨基甲酰基-、氟-、氯-、溴-、甲基-、乙基-、正或异丙基-、正-、异-、仲-或叔-丁基-、三氟甲基-、甲氧基-、乙氧基-、正或异丙氧基-、甲硫基-、乙硫基-、甲基亚磺酰基-、乙基亚磺酰基-、甲基磺酰基-、乙基磺酰基-、乙酰基-、丙酰基-、甲氧基羰基-、乙氧基羰基-、正或异丙氧基羰基取代的苯基羰基、苯基甲基羰基或苯基乙基羰基,
R3还代表各任选由氰基-、羧基-、氨基甲酰基-、硫代氨基甲酰基-、氟-、氯-、溴-、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-、甲基亚磺酰基-、乙基亚磺酰基-、甲基磺酰基-、乙基磺酰基-、乙酰基-、丙酰基-、甲氧基羰基-、乙氧基羰基-、正或异丙氧基羰基-、苯基-、苯氧基-或苯硫基-取代的呋喃基羰基、四氢呋喃基羰基、噻吩基羰基、四氢噻吩基羰基、噁唑基羰基、异噁唑基羰基、噻唑基羰基、噁二唑基羰基、噻二唑基羰基、吡唑基羰基、吡啶基羰基或嘧啶基羰基,
R4代表氢或代表各任选由氰基-、羧基-、氟-、氯-、甲氧基-、乙氧基-、正或异丙氧基-、乙酰基-、丙酰基-、甲氧基羰基-、乙氧基羰基-、正或异丙氧基羰基-取代的甲基、乙基、正或异丙基、正-、异-、仲-或叔丁基、正-、异-、仲-或叔戊基、乙酰基、正或异丙基羰基、正-、异-、仲-或叔丁基羰基、丙烯基、丙烯基羰基、丁烯基、丁烯基羰基、戊烯基、戊烯基羰基、丙炔基、丙炔基羰基、丁炔基、丁炔基羰基、戊炔基或戊炔基羰基,
R4还代表各任选由氰基-、羧基-、氟-、氯-、溴-、甲基-、乙基-、正或异丙基-、甲氧基-、乙氧基-、正或异丙氧基-、乙酰基-或丙酰基-、甲氧基羰基-、乙氧基羰基-、正或异丙氧基羰基-取代的环丙基、环丙基羰基、环丁基、环丁基羰基、环戊基、环戊基羰基、环己基、环己基羰基、环丙基甲基、环丁基甲基、环戊基甲基或环己基甲基,
R4还代表各任选由氰基-、羧基-、硝基-、氨基甲酰基-、硫代氨基甲酰基-、氟-、氯-、溴-、甲基-、乙基-、正或异丙基-、正-、异-、仲-或叔-丁基-、三氟甲基-、甲氧基-、乙氧基-、正或异丙氧基-、甲硫基-、乙硫基-、甲基亚磺酰基-、乙基亚磺酰基-、甲基磺酰基-、乙基磺酰基-、乙酰基-、丙酰基-、甲氧基羰基-、乙氧基羰基-、正或异丙氧基羰基-取代的苯基羰基、苯基甲基羰基或苯基乙基羰基,
R4还代表各任选由氰基-、羧基-、氨基甲酰基-、硫代氨基甲酰基-、氟-、氯-、溴-、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-、甲基亚磺酰基-、乙基亚磺酰基-、甲基磺酰基-、乙基磺酰基-、乙酰基-、丙酰基-、甲氧基羰基-、乙氧基羰基-、正或异丙氧基羰基-、苯基-、苯氧基-或苯硫基-取代的呋喃基羰基、四氢呋喃基羰基、噻吩基羰基、四氢噻吩基羰基、噁唑基羰基、异噁唑基羰基、噻唑基羰基、噁二唑基羰基、噻二唑基羰基、吡唑基羰基、吡啶基羰基或嘧啶基羰基,
R4与R3一起代表各任选由氟-、氯-、甲基-或三氟甲基-取代的丙-1,3-二基(三亚甲基)、丁-1,4-二基(四亚甲基)、1-氧代-丙-1,3-二基、1-氧代-丁-1,4-二基、1,3-二氧代丙-1,3-二基或1,4-二氧代丁-1,4-二基,
R5代表氢、氟、氯、溴或甲基,
R6代表甲基、乙基、二氟甲基、二氯甲基、三氟甲基、三氯甲基、氯二氟甲基、氟二氯甲基、氯乙基、氟乙基、二氟乙基、二氯乙基、氯氟乙基、氯二氟乙基、氟二氯乙基、三氟乙基、四氟乙基、氯三氟乙基或五氟乙基,
R7代表氢或代表各任选由氟-、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-、或仲-丁氧基、丙烯基、丁烯基、丙炔基或丁炔基,且
R8代表氢或代表各任选由氟-、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-、或仲-丁氧基、丙烯基、丁烯基、丙炔基或丁炔基。
上面所列的基团定义—不论是一般的或是在优选范围中所列的—不仅适合于式(I)的终产物,而且也相应地适合于所有制备中所需的起始原料和/或中间体。这些基团也可以按需要相互组合,而且也包括所指的优选范围间的组合。
本发明式(I)化合物的实例列于下文的组中。
R3具有例如下面所列的含义:
氢、甲基、乙基、正或异丙基、正-、异-、仲-或叔丁基、正-、异-、仲-或叔戊基、乙酰基、正-或异丙基-羰基、正-、异-、仲-或叔丁基羰基、正-、异-、仲-或叔戊基羰基、二氟乙酰基、三氟乙酰基、氯二氟乙酰基、氟二氯乙酰基、氟丙酰基、氯丙酰基、氯氟丙酰基、二氟丙酰基、二氯丙酰基、三氟丙酰基、三氯丙酰基、氯二氟丙酰基、四氟丙酰基、氯三氟丙酰基、五氟丙酰基、氟丁酰基、氯丁酰基、二氟丁酰基、二氯丁酰基、三氟丁酰基、氰基甲基、氰基乙酰基、氰基乙基、氰基丙酰基、氰基丙基、氰基丁酰基、羧基甲基、羧基乙基、羧基丙基、羧基丁基、甲氧基甲基、甲氧基乙酰基、乙氧基甲基、乙氧基乙酰基、丙氧基甲基、丙氧基乙酰基、甲氧基乙基、甲氧基丙酰基、乙氧基乙基、丙氧基乙基、甲氧基丙基、甲氧基丁酰基、乙氧基丙基、乙氧基丁酰基、甲氧基羰基甲基、乙氧基羰基甲基、丙氧基羰基甲基、甲氧基羰基乙基、乙氧基羰基乙基、丙氧基羰基乙基、甲氧基羰基丙基、乙氧基羰基丙基、1-丙烯-3-基(烯丙基)、3-甲基-1-丙烯-3-基、2-丁烯-4-基(巴豆基)、1-丙炔-3-基(炔丙基)、3-甲基-1-丙炔-3-基、2-丁炔-4-基、环丙基、环丙基羰基、氰基环丙基、羧基环丙基、二氟环丙基、二氯环丙基、甲基环丙基、甲氧基羰基环丙基、乙氧基羰基环丙基、环丁基、环丁基羰基、氰基环丁基、羧基环丁基、二氟环丁基、二氟环丁基羰基、三氟环丁基、三氟环丁基羰基、四氟环丁基、四氟环丁基羰基、氯三氟环丁基、氯三氟环丁基羰基、甲基环丁基、环戊基、环戊基羰基、氰基环戊基、羧基环戊基、氟环戊基、氯环戊基、二氟环戊基、二氯环戊基、甲基环戊基、甲氧基羰基环戊基、乙氧基羰基环戊基、环己基、环己基羰基、氰基环己基、羧基环己基、氟环己基、氯环己基、二氟环己基、二氯环己基、甲基环己基、三氟甲基环己基、甲氧基羰基环己基、乙氧基羰基环己基、环丙基甲基、二氟环丙基甲基、三氯环丙基甲基、环丁基甲基、环戊基甲基、环己基甲基、氰基环己基甲基、羧基环己基甲基、氟环己基甲基、氯环己基甲基、甲基环己基甲基、三氟甲基环己基甲基、苯甲酰基、氰基苯甲酰基、硝基苯甲酰基、氟苯甲酰基、氯苯甲酰基、溴苯甲酰基、甲基苯甲酰基、三氟甲基苯甲酰基、甲氧基苯甲酰基、二氟甲氧基苯甲酰基、三氟甲氧基苯甲酰基、苯基乙酰基、呋喃基羰基、四氢呋喃基羰基、噻吩基羰基、四氢噻吩基羰基、噁唑基羰基、异噁唑基羰基、吡啶基羰基。
R3具有例如上面对第1组所给的含义。
R3具有例如上面对第1组所给的含义。
第4组
R3具有例如上面对第1组所给的含义。
第5组
R3具有例如上面对第1组所给的含义。
R3具有例如上面对第1组所给的含义。
R3具有例如上面对第1组所给的含义。
第8组
R3具有例如上面对第1组所给的含义。
R3具有例如上面对第1组所给的含义。
R3具有例如上面对第1组所给的含义。
第11组
R3具有例如上面对第1组所给的含义。
使用(例如)3-氨基-4-氯二氟甲基-1-(4-氰基-2-氟-5-甲基磺酰基氨基-苯基)-3,6-二氢-2,6-二氧代-1(2H)-嘧啶和二氯乙酰基氯作为起始原料,本发明方法的反应途径可以用下列反应式说明:
式(II)给出的是在本发明制备式(I)化合物的方法中用作起始原料的氨基尿嘧啶的一般定义。在式(II)中,R1、R2、R5、R6、R7和R8优选或特别优选在关于式(I)化合物的描述中在上面已经指明的R1、R2、R5、R6、R7和R8的优选或特别优选的含义;Z优选代表任选由卤素取代的C1-C4-烷基磺酰基氨基、氨基或任选由卤素取代的C1-C4-烷基羰基氨基,特别是甲基磺酰基氨基、乙基磺酰基氨基或三氟乙酰基氨基。
式(II)起始原料是已知的和/或可以通过已知的方法制备(参见,EP408 382、EP 648 749)。
式(III)、(IV)、(V)和(VI)给出的是在本发明制备式(I)化合物的方法中另用作起始原料的烷基化或酰基化试剂的一般定义。在这些化学式中,R3和R4优选或特别是在关于式(I)化合物的描述中在上面已经指明的R3和R4的优选或特别优选的含义。
式(III)、(IV)、(V)和(VI)起始原料是已知的合成化学品。
制备式(I)化合物的本发明方法优选在适合的反应助剂存在下进行的。适合的反应助剂一般是所有的常规无机或有机碱或酸受体。它们包括优选是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、氢氧化物或醇化物,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、氢氧化钾或氢氧化铵、甲醇钠或甲醇钾、乙醇钠或乙醇钾、正或异丙醇钠或正或异丙醇钾、正-、异-、仲-或叔丁醇钠或正-、异-、仲-或叔丁醇钾;以及碱性有机氮化合物,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-二甲基苄胺、吡啶、2-甲基-、3-甲基-和4-甲基、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)和1,8-二氮杂二环[5,4,0]-十一碳-7-烯(DBU)。
制备式(I)化合物的本发明方法优选是在稀释剂存在下进行的。适合的稀释剂是一般是常规的有机溶剂。这些溶剂包括优选是脂族、脂环族和芳族的任选卤代的烃,诸如戊烷、己烷、庚烷、石油醚、轻石油、汽油、苯、甲苯、二甲苯、氯苯、二氯苯、环己烷、甲基环己烷、二氯甲烷、氯仿和四氯化碳;二烷基醚类,如,乙醚、二异丙醚、甲基叔丁基醚(MTBE)、乙基叔丁基醚、甲基叔戊基醚(TAME)、乙基叔戊基醚、四氢呋喃、1,4-二噁烷、乙二醇二甲醚或乙二醇二乙醚、二甘醇二甲醚或二甘醇二乙醚;二烷基酮类,如,丙酮、丁酮(甲基乙基酮)、甲基异丙基酮或甲基异丁基酮;腈类,如,乙腈、丙腈、丁腈或苯甲腈;酰胺类,如N,N-二甲基甲酰胺(DMF)、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、乙酸乙酯、乙酸正或异丙酯、乙酸正、异或仲丁酯;亚砜类,如二甲亚砜;烷醇类,如,甲醇、乙醇、正或异丙醇、正、异、仲或叔丁醇、乙二醇单甲醚或乙二醇单乙醚、二甘醇单甲醚或二甘醇单乙醚;其与水的混合物或纯水。
实施本发明方法时,反应温度可以在相对宽的范围内变化。一般而言,反应是在0℃和150℃之间,优选采用10℃至120℃间的温度下进行。
本发明方法通常是在常压下进行的。然而,也可以在增高或降低的压力—通常在0.1巴至10巴间进行的。
实施本发明方法时,起始原料通常是以大致等摩尔量进行的。然而,也可以相对大地过量使用组分之一。反应通常是在适合的稀释剂中,在反应助剂存在下进行,且反应混合物通常在所需的温度下搅拌几小时。后处理是通过常规的方法来完成的(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(haulmkiller),特别是用作除草剂。所谓的杂草,就其最广的含义而言,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作为选择性除草剂基本上取决于所用的量。
本发明化合物可以用于下列植物:
下列属的双子叶杂草:芥属、独行草属、猪殃殃属、繁缕属、母草属、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、野豌豆属、烟草属、蕃茄属、花生属、芸苔属、莴苣属、黄瓜属和南瓜属。
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、蔍草属、雀稗属、鸭嘴草属、尖瓣花属、龙爪茅属、剪股颖属、看麦娘属和风草属。
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、天门冬属和葱属。
然而,本发明化合物的应用决不仅限于这些属,它们也可以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、香蕉种植园、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、草皮和牧场中的杂草,和选择性地防治一年生作物中的杂草。
本发明式(I)化合物特别适合于选择性地以芽前和芽后二种方式防治单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剂型,如液剂、乳剂、可湿性粉剂、悬浮剂、粉剂、喷粉药剂、膏剂、可溶性粉剂、颗粒剂、悬乳剂、用活性化合物浸渍的天然和合成物质和用聚合物制成的微胶囊。
这些型剂可以用已知的方式生产,例如,将活性化合物与填充剂,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。
在用水作填充剂的情况下,也可以用有机溶剂作助溶剂。作为液体溶剂,适合的主要有:芳族化合物,如二甲苯,甲苯或烷基萘,氯代芳烃或氯代脂肪烃,如氯代苯类、氯乙烯类或二氯甲烷,脂族烃,如环己烷或石蜡,例如矿物油馏份、矿物和植物油,醇类,如丁醇或乙二醇以及其醚和酯,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;用于颗粒剂的固体载体适合的有: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。其它的添加物可以是矿物油和植物油。
也可能使用染料,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%。
防治杂草时,本发明活性化合物也可以—以其本身或以其制剂形式—以与已知除草剂混合的混合物、成品制剂或可能的桶混物的形式使用。
可以用于混合物的组分是已知的除草剂,例如酰苯胺类如吡氟草胺和敌稗;芳基羧酸类如二氯吡啶甲酸、麦草畏和毒草定;芳氧基链烷酸类如2,4-滴、2,4-滴丁酸、2,4-滴丙酸、氟草烟、2甲4氯、2甲4氯丙酸和绿草定;芳氧基苯氧基链烷酸类如禾草灵、恶唑禾草灵、吡氟禾草灵、吡氟氯禾灵和喹禾灵;连氮酮类如杀草敏和哒草伏;氨基甲酸酯类如氯苯胺灵、甜菜安、甜菜宁和苯胺灵;氯乙酰苯胺类如甲草胺、乙草胺、丁草胺、吡草胺、异丙甲草胺、丙草胺和毒草胺;二硝基苯胺类如安磺灵、二甲戊乐灵和氟乐灵;二苯醚类如三氟羧草醚、甲羧除草醚、乙羧氟草醚、氟黄胺草醚、halosafen、乳氟禾草灵和乙氧氟草醚;脲类如绿麦隆、敌草隆、伏草隆、异丙隆、利谷隆和甲基苯噻隆;羟胺类如禾草灭、烯草酮、噻草酮、稀禾定和肟草酮;咪唑啉酮类如咪草烟、咪草酯、灭草烟和灭草喹;腈类如溴苯腈、敌草腈和碘苯腈;氧乙酰胺类如苯噻草胺;磺酰脲类如amidosufuron、苄嘧黄隆、氯嘧黄隆、绿黄隆、醚黄隆、甲黄隆、烟嘧黄隆、氟嘧黄隆、吡嘧黄隆、噻黄隆、醚苯黄隆和苯黄隆;硫代氨基甲酸酯类如丁草特、灭草特、燕麦敌、茵达灭、禾草畏、草达灭、苄草丹、杀草丹和野麦畏;三嗪类如莠去津、氰草津、西玛津、西草净和特丁净;噻嗪酮类如环嗪酮、苯嗪草酮和嗪草酮;其它除草剂如杀草强、呋草黄、灭草松、环庚草醚、异恶草酮、二氯吡啶酸、双苯唑快、氟硫草定、乙呋草黄、氟咯草酮、草铵膦、草甘膦、isoxaben、哒草特、二氯喹啉酸、喹草酸、草硫膦和灭草环。
也可以是与其它已知活性化合物的混合物,如杀菌剂、杀虫剂、杀螨剂、杀线虫剂、驱鸟剂、植物营养素和土壤结构改良剂。
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,所述的使用形式有例如可直接使用溶液、悬浮液、乳液、粉、膏和颗粒。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,使用量在每公顷土地表面积用1克至10公斤之间,优选每公顷5克至5公斤。
本发明活性成分的制备和使用可以参见下列实施例。
制备实施例:
实施例1
将2.1克(5毫摩尔)3-氨基-1-(4-氰基-2-氟-5-乙基磺酰基-氨基-苯基)-5-三氟甲基-3,6-二氢-2,6-二氧代-1(2H)-嘧啶、1.1克(5.5毫摩尔)三氟乙酸酐、1毫升三乙胺和20毫升乙腈的混合物回流加热30小时,之后用水泵真空浓缩。残留物用乙酸乙酯消化,用1N盐酸洗涤,用硫酸钠干燥并过滤。滤液用水泵真空浓缩,并将以残留物获得的粗产物通过柱色谱(硅胶,氯仿/乙酸乙酯,体积比1∶1)纯化。
获得0.8克(理论值的38%)3-氨基-1-(4-氰基-2-氟-5-三氟乙酰基-氨基-苯基)-5-三氟甲基-3,6-二氢-2,6-二氧代-1(2H)-嘧啶。
1H NMR(二甲基亚砜-D6,δ):6.47ppm。
类似于实施例1的方法和根据本发明方法的一般描述,还可以制备例如列于下表1中的式(I)化合物。
表1:式(I)化合物的实施例实施例 R1 R2 R3 R4 R5 R6 R7 R8 物理序号 数据2 F CN H H H CF3 H H3 F CN H CH3 H CF3 H H4 F CN CH3 CH3 H CF3 H H5 F CN CH3 C3H7-i H CF3 H H6 F CN H C2H5 H CF3 H H7 F CN H C3H7-n H CF3 H H8 F CN H C3H7-i H CF3 H H9 F CN -(CH2)4- H CF3 H H10 F CN H COCF3 H CF3 H H11 F CN H COC2F5 H CF3 H H12 F CN H COCH3 H CF3 H H13 F CN COCH3 COCH3 H CF3 H H14 F CN -CO-CH2CH2-CO- H CF3 H H15 F CN H COC2H5 H CF3 H H实施例 R1 R2 R3 R4 R5 R6 R7 R8 物理序号 数据16 F CN H
H CF3 H H17 F CN H
H CF3 H H18 F CN H
H CF3 H H19 F CN H COC4H9-t H CF3 H H20 F CN H COC3H7-i H CF3 H H2l F CN CH3 COCH3 H CF3 H H22 F CN C2H5 COC4H9-n H CF3 H H23 F CN CH3 COCF3 H CF3 H H24 F CN COCH3
H CF3 H H25 F CN H CH2COOCH3 H CF3 H H26 F CN CH3 CH2COOCH3 H CF3 H H27 F CN COCH3 CH2CN H CF3 H H28 F CN H CH2CH2CN H CF3 H H29 F CSNH2 H COCF3 H CF3 H H实施例 R1 R2 R3 R4 R5R6 R7 R8 物理序号 数据30 F CN H COCHCl2 H CF3 H H31 F CN
H CF3 H H32 F CN
H CF3 H H33 F CN H CH3 H CF3 CH3 H34 F CSNH2 H CH3 H CF3 CH3 H35 F CN H
H CF3 H H
应用实施例
实施例A
芽前试验
溶剂: 5重量份丙酮
乳化剂: 1重量份的烷芳基聚乙二醇醚
制备适合的活性化合物制剂时,将1重量份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。24小时后,土壤用活性化合物制剂浇灌。最好使每单位面积的水量保持恒定。制剂中活性化合物的浓度是不重要的,只有每单位施用的活性化合物的量是关键的。
三周后,将植物的损害程度与未处理对照样的发育相比较,定出损害%。
数值的含义如下:
0%=无作用(与未处理对照样相同)
100%=完全损害
在此试验中,例如,制备实施例1化合物在30克/公顷的施用量下,对杂草显示出非常强的活性,例如狗尾草(100%)、蜀黍(90%)、苘麻(100%)、猪殃殃(100%)、母菊(100%)和蓼(100%),而作物对之则有非常优异的耐受性,例如玉米(0%)。
实施例B
芽后试验
溶剂: 5重量份丙酮
乳化剂: 1重量份的烷芳基聚乙二醇醚
制备适合的活性化合物制剂时,将1重量份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。选择好喷雾浓度,使得以1000升/公顷的喷雾量施用所需的活性化合物量。
三周后,将植物的损害程度与未处理对照样的发育相比较,定出损害%。
数值的含义如下:
0%=无作用(与未处理对照样相同)
100%=完全破坏
在此试验中,例如,制备实施例1的化合物在30克/公顷的施用量下,对杂草显示出非常强的活性,如稗(100%)、苘麻(100%)、曼陀罗(100%)、牵牛(100%)和堇菜(100%),而作物对之则有非常优异的耐受性,例如玉米(0%)。
Claims (6)
1.通式(I)的取代的氨基尿嘧啶类化合物
其中
R1代表氢、氟或氯,
R2代表氰基或硫代氨基甲酰基,
R3代表氢或代表各任选由氰基-、羧基-、氟-或氯-取代的甲基、乙基、正或异丙基、正-、异-、仲-或叔丁基、正-、异-、仲-或叔戊基、乙酰基、正或异丙基羰基、正-、异-、仲-或叔丁基羰基,
R3还代表各任选由氰基-、羧基-、氟-、氯-或溴-取代的环丙基、环丙基羰基、环丁基、环丁基羰基、环戊基、环戊基羰基、环己基或环己基羰基,
R4代表各任选由氰基-、羧基-、氟-、氯-、甲氧基-、乙氧基-、正或异丙氧基-、乙酰基-、丙酰基-、甲氧基羰基-、乙氧基羰基-、正或异丙氧基羰基-取代的甲基、乙基、正或异丙基、正-、异-、仲-或叔丁基、正-、异-、仲-或叔戊基、乙酰基、正或异丙基羰基、正-、异-、仲-或叔丁基羰基、丙烯基、丙烯基羰基、丁烯基、丁烯基羰基、戊烯基、戊烯基羰基、丙炔基、丙炔基羰基、丁炔基、丁炔基羰基、戊炔基或戊炔基羰基,
R4还代表各任选由氰基-、羧基-、氟-、氯-、溴-、甲基-、乙基-、正或异丙基-、甲氧基-、乙氧基-、正或异丙氧基-、乙酰基-或丙酰基-、甲氧基羰基-、乙氧基羰基-、正或异丙氧基羰基-取代的环丙基、环丙基羰基、环丁基、环丁基羰基、环戊基、环戊基羰基、环己基、环己基羰基,
R4还代表各任选由氰基-、羧基-、硝基-、氨基甲酰基-、硫代氨基甲酰基-、氟-、氯-、溴-、甲基-、乙基-、正或异丙基-、正-、异-、仲-或叔-丁基-或三氟甲基-取代的苯基羰基、苯基甲基羰基或苯基乙基羰基,
R4还代表各任选由氰基-、羧基-、氨基甲酰基-、硫代氨基甲酰基-、氟-、氯-、溴-、甲基-或乙基-取代的噻吩基羰基或吡啶基羰基,或
R4与R3一起代表各任选由氟-、氯-、甲基-或三氟甲基-取代的丙-1,3-二基(三亚甲基)、丁-1,4-二基(四亚甲基)、1-氧代-丙-1,3-二基、1-氧代-丁-1,4-二基、1,3-二氧代丙-1,3-二基或1,4-二氧代丁-1,4-二基,
R5代表氢、氟、氯或溴,
R6代表甲基、乙基、二氟甲基、二氯甲基、三氟甲基、三氯甲基、氯二氟甲基、氟二氯甲基、氯乙基、氟乙基、二氯乙基、氯氟乙基、氯二氟乙基、氟二氯乙基、三氟乙基、四氟乙基、氯三氟乙基或五氟乙基,
R7代表氢或代表各任选由氟-或氯-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、正或异丙氧基或正-、异-、或仲-丁氧基,且
R8代表氢或代表各任选由氟-、氯-、甲氧基-或乙氧基-取代的甲基或乙基。
3.除草剂组合物,其特征在于,它含有至少一种根据权利要求1的通式(I)的取代的氨基尿嘧啶类化合物。
4.防治莠草的方法,其特征在于,使根据权利要求1的通式(I)的取代的氨基尿嘧啶类化合物作用于莠草和/或其栖生地。
5.根据权利要求1的通式(I)的取代的氨基尿嘧啶类化合物防治莠草的应用。
6.制备除草剂组合物的方法,其特征在于,将根据权利要求1的通式(I)的取代的氨基尿嘧啶类化合物与填充剂和/或表面活性物质混合。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19532344A DE19532344A1 (de) | 1995-09-04 | 1995-09-04 | Substituierte Aminouracile |
DE19532344.0 | 1995-09-04 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1195341A CN1195341A (zh) | 1998-10-07 |
CN1108293C true CN1108293C (zh) | 2003-05-14 |
Family
ID=7771056
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN96196722A Expired - Fee Related CN1108293C (zh) | 1995-09-04 | 1996-08-22 | 取代的1-氨基-3-苯基-尿嘧啶衍生物、其制备及其作为除草剂的应用 |
Country Status (10)
Country | Link |
---|---|
US (1) | US6008160A (zh) |
EP (1) | EP0851861A1 (zh) |
JP (1) | JPH11512102A (zh) |
KR (1) | KR19990044255A (zh) |
CN (1) | CN1108293C (zh) |
AU (1) | AU705631B2 (zh) |
BR (1) | BR9610194A (zh) |
CA (1) | CA2230650A1 (zh) |
DE (1) | DE19532344A1 (zh) |
WO (1) | WO1997009319A1 (zh) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1673219A (zh) | 1997-10-27 | 2005-09-28 | Isk美国有限公司 | 取代的苯化合物、它们的制备方法和含它们的除草剂和脱叶剂组合物 |
DE19830694A1 (de) | 1998-07-09 | 2000-01-13 | Bayer Ag | Substituierte Acylaminophenyl-uracile |
DE10219434A1 (de) * | 2002-05-02 | 2003-11-20 | Bayer Cropscience Ag | Substituierte (Thioxo)carbonylaminophenyl-uracile |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
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DE2207549A1 (de) * | 1972-02-18 | 1973-08-23 | Bayer Ag | 1-aminouracile und deren salze, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
EP0420194A2 (en) * | 1989-09-26 | 1991-04-03 | Sumitomo Chemical Company, Limited | Uracil derivatives and their production and use |
EP0438209A1 (en) * | 1990-01-18 | 1991-07-24 | Nissan Chemical Industries, Limited | Uracil derivatives and pesticides containing the same as active ingredient |
EP0517181A1 (en) * | 1991-06-07 | 1992-12-09 | Sumitomo Chemical Company, Limited | Amino uracil derivatives, and their production and use |
EP0540023A1 (en) * | 1991-11-01 | 1993-05-05 | Sumitomo Chemical Company, Limited | Uracil derivatives and their use |
EP0563384A1 (en) * | 1990-12-17 | 1993-10-06 | Nissan Chemical Industries, Limited | Uracil derivative |
CN1102642A (zh) * | 1993-08-18 | 1995-05-17 | 拜尔公司 | N-氰基芳基-氮杂环 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2441156A1 (de) * | 1974-08-28 | 1976-03-18 | Bayer Ag | 1-furfurylamino-uracile, ein verfahren zu ihrer herstellung sowie ihre verwendung als herbizide |
US5681794A (en) * | 1993-08-18 | 1997-10-28 | Bayer Aktiengesellschaft | N-cyanoaryl-nitrogen heterocycles |
JP4036468B2 (ja) * | 1994-04-25 | 2008-01-23 | バイエル・アクチエンゲゼルシヤフト | N−シアノアリール窒素複素環 |
-
1995
- 1995-09-04 DE DE19532344A patent/DE19532344A1/de not_active Withdrawn
-
1996
- 1996-08-22 WO PCT/EP1996/003693 patent/WO1997009319A1/de not_active Application Discontinuation
- 1996-08-22 CN CN96196722A patent/CN1108293C/zh not_active Expired - Fee Related
- 1996-08-22 US US09/029,212 patent/US6008160A/en not_active Expired - Fee Related
- 1996-08-22 KR KR1019980701491A patent/KR19990044255A/ko active IP Right Grant
- 1996-08-22 JP JP9510813A patent/JPH11512102A/ja not_active Ceased
- 1996-08-22 AU AU68762/96A patent/AU705631B2/en not_active Ceased
- 1996-08-22 CA CA002230650A patent/CA2230650A1/en not_active Abandoned
- 1996-08-22 BR BR9610194A patent/BR9610194A/pt unknown
- 1996-08-22 EP EP96929303A patent/EP0851861A1/de not_active Withdrawn
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2207549A1 (de) * | 1972-02-18 | 1973-08-23 | Bayer Ag | 1-aminouracile und deren salze, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
EP0420194A2 (en) * | 1989-09-26 | 1991-04-03 | Sumitomo Chemical Company, Limited | Uracil derivatives and their production and use |
EP0438209A1 (en) * | 1990-01-18 | 1991-07-24 | Nissan Chemical Industries, Limited | Uracil derivatives and pesticides containing the same as active ingredient |
EP0563384A1 (en) * | 1990-12-17 | 1993-10-06 | Nissan Chemical Industries, Limited | Uracil derivative |
EP0517181A1 (en) * | 1991-06-07 | 1992-12-09 | Sumitomo Chemical Company, Limited | Amino uracil derivatives, and their production and use |
EP0540023A1 (en) * | 1991-11-01 | 1993-05-05 | Sumitomo Chemical Company, Limited | Uracil derivatives and their use |
CN1102642A (zh) * | 1993-08-18 | 1995-05-17 | 拜尔公司 | N-氰基芳基-氮杂环 |
Also Published As
Publication number | Publication date |
---|---|
AU705631B2 (en) | 1999-05-27 |
KR19990044255A (ko) | 1999-06-25 |
JPH11512102A (ja) | 1999-10-19 |
CN1195341A (zh) | 1998-10-07 |
AU6876296A (en) | 1997-03-27 |
WO1997009319A1 (de) | 1997-03-13 |
CA2230650A1 (en) | 1997-03-13 |
BR9610194A (pt) | 1998-12-15 |
EP0851861A1 (de) | 1998-07-08 |
US6008160A (en) | 1999-12-28 |
DE19532344A1 (de) | 1997-03-06 |
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