CN1350517A - 取代的n-氰基脒类化合物 - Google Patents
取代的n-氰基脒类化合物 Download PDFInfo
- Publication number
- CN1350517A CN1350517A CN00807457A CN00807457A CN1350517A CN 1350517 A CN1350517 A CN 1350517A CN 00807457 A CN00807457 A CN 00807457A CN 00807457 A CN00807457 A CN 00807457A CN 1350517 A CN1350517 A CN 1350517A
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- China
- Prior art keywords
- amino
- group
- carbonyl
- alkyl
- sec
- Prior art date
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- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 5
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 3
- -1 nitro- Chemical class 0.000 claims description 141
- 150000001875 compounds Chemical class 0.000 claims description 41
- 238000002360 preparation method Methods 0.000 claims description 25
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 16
- 150000001336 alkenes Chemical class 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 150000001721 carbon Chemical group 0.000 claims description 7
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000001924 cycloalkanes Chemical class 0.000 claims description 6
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 6
- 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 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 230000002363 herbicidal effect Effects 0.000 claims description 5
- 229950001891 iprotiazem Drugs 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 3
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 3
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 3
- 125000006627 ethoxycarbonylamino group Chemical group 0.000 claims description 3
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 3
- 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 3
- 125000006629 isopropoxycarbonylamino group Chemical group 0.000 claims description 3
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 3
- 125000006626 methoxycarbonylamino group Chemical group 0.000 claims description 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 3
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 3
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 3
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims description 2
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 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
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 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
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 2
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 abstract description 4
- 239000004009 herbicide Substances 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 25
- 150000004702 methyl esters Chemical class 0.000 description 12
- 244000025254 Cannabis sativa Species 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 8
- 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
- 239000002904 solvent Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- 239000013543 active substance Substances 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 125000004494 ethyl ester group Chemical group 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- 235000010755 mineral Nutrition 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 241000209140 Triticum Species 0.000 description 4
- 235000021307 Triticum Nutrition 0.000 description 4
- 230000001419 dependent effect Effects 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
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- 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
- 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
- 239000003516 soil conditioner Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000000967 suction filtration Methods 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
- 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 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
- 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
- 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
- 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
- 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
- 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
- 238000005406 washing Methods 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
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Abstract
本发明涉及新颖的通式(I)的取代的N-氰基脒类,其中,R1代表氢或代表各任选被取代的烷基、烯基、炔基、环烷基、环烷基烷基、芳基或芳烷基和R2代表各苯并稠合的、吡啶并稠合的或噻吩并稠合的环烷(烯)基、氧杂环烷(烯)基或硫杂环烷(烯)基,其中所有的环状或杂环状基团可以被取代。本发明还涉及所述的取代的N-氰基脒的制备方法以及它们作为除草剂的应用。
Description
本发明涉及新颖的取代的N-氰基脒类化合物、其制备及其作为除草剂的应用。
业已知道某些取代的N-氰基胍类具有除草性能(参见,例如,DE-A-2505301、US-A-4661520、US-A-4684398、US-A-4689348、J.Agric.Food Chem.37(1989),809-814)。然而,现有技术中的取代的N-氰基胍类的性能和各个方面不能满足现代作物处理剂的高要求。
本发明提供新颖的通式(I)的取代的N-氰基脒类,其中R1 代表氢或代表各任选被取代的烷基、烯基、炔基、环烷基、环烷基烷基、芳基或芳烷基和R2 代表各苯并稠合的、吡啶并稠合的或噻吩并稠合的环烷(烯)基、氧杂环烷(烯)基或硫杂环烷(烯)基,其中所有的环状或杂环状基团可以被取代。
通式(I)包括在每一种情况下可能存在的E和Z构型异构体。
在基团定义中,烃链如烷基、烯基或炔基,各可以是直链或支链。
列于上下文提到的化学式中的基团的优选的取代基说明如下。R1 优选代表氢,代表任选由氰基-、卤素-、C1-C4-烷氧基-、C1-C4-烷硫基-、C1-C4-烷基亚磺酰基-或C1-C4-烷基磺酰基-取代的具有1至6个碳原子的烷基,代表各任选由卤素-取代的各具有2至6个碳原子的烯基或炔基,代表各任选由氰基-、卤素-或C1-C4-烷基-取代的在环烷基中各具有3至6个碳原子和任选在烷基部分具有1至4个碳原子的环烷基或环烷基烷基,或代表各任选由硝基-、氰基-、卤素-、C1-C4-烷基-、C1-C4-卤代烷基-、C4-C4-烷氧基-或C1-C4-卤代烷氧基-取代的在芳基部分各具有6或10个碳原子和任选在烷基部分具有1至4个碳原子的芳基或芳烷基。R2 优选代表选自下文所列的各苯并稠合的、吡啶并稠合的或噻吩并稠合的环烷(烯)基、氧杂环烷(烯)基或硫杂环烷(烯)基,其中所有的环状或杂环状基团可以被取代:其中所有的环状或杂环状基团可以优选由下文所列基团之一取代:硝基、羟基、氨基、氰基、氨基甲酰基、硫代氨基甲酰基、甲酰基氨基、卤素、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷硫基、C1-C4-卤代烷硫基、C1-C4-烷基亚磺酰基、C1-C4-卤代烷基亚磺酰基、C1-C4-烷基磺酰基、C1-C4-卤代烷基磺酰基、C1-C4-烷基氨基、二-(C1-C4-烷基)-氨基、C1-C4-烷基-羰基、C1-C4-烷氧基-羰基、C1-C4-烷基氨基-羰基、二-(C1-C4-烷基)-氨基-羰基、C1-C4-烷基-羰基-氨基、C1-C4-烷氧基-羰基-氨基、C1-C4-烷基-氨基-羰基-氨基、C1-C4-烷基-磺酰基-氨基。R1 特别优选代表氢,代表各任选由氰基-、氟-、氯-、溴-、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-、正或异丙基亚磺酰基-、甲基磺酰基-、乙基磺酰基-、正或异丙基磺酰基-取代的甲基、乙基、正或异丙基、正-、异-、仲-或叔丁基,代表各任选由氟-、氯-或溴-取代的乙烯基、丙烯基、丁烯基、乙炔基、丙炔基或丁炔基,代表各任选由氰基-、氟-、氯-、溴-、甲基-、乙基-、正或异丙基-取代的环丙基、环丁基、环戊基、环己基、环丙基甲基、环丁基甲基、环戊基甲基或环己基甲基,或代表各任选由硝基-、氰基-、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-、二氟甲氧基-或三氟甲氧基-取代的苯基或苄基。R2 特别优选代表上文提到的环状或杂环状基团之一,其中取代基可以选自下文所列的基团之一:硝基、羟基、氨基、氰基、氨基甲酰基、硫代氨基甲酰基、甲酰基氨基、氟、氯、溴、甲基、乙基、正或异丙基、正、异、仲或叔丁基、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、甲氧基、乙氧基、正或异丙氧基、二氟甲氧基、三氟甲氧基、氯二氟甲氧基、氟二氯甲氧基、甲硫基、乙硫基、正或异丙硫基、二氟甲硫基、三氟甲硫基、氯二氟甲硫基、氟二氯甲硫基、甲基亚磺酰基、乙基亚磺酰基、三氟甲基亚磺酰基、甲基磺酰基、乙基磺酰基、三氟甲基磺酰基、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、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、二甲基氨基羰基、二乙基氨基羰基、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、甲基氨基羰基氨基、乙基氨基羰基氨基、正或异丙基氨基羰基氨基、甲基磺酰基氨基、乙基磺酰基氨基、正或异丙基磺酰基氨基。R1 非常特别优选代表氢或代表各任选由氰基-、氟-、氯-、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-取代的甲基、乙基、正或异丙基。R2 非常特别优选代表列于下文的苯并稠合的环烷(烯)基:其中所有的环状基团可以由下文所列的基团之一取代:R1 最优选代表氢、甲基、乙基或正或异丙基。R2 最优选代表下列的基团之一:
本发明优选的是含有上面所列优选含义组合的式(I)化合物。
本发明特别优选的是含有上面所列特别优选含义组合的式(I)化合物。
本发明非常特别优选的是含有上面所列非常特别优选含义组合的式(I)化合物。
本发明最优选的是含有上面所列最优选含义组合的式(I)化合物。
列于上文中的一般或优选的基团定义适合于式(I)的终产物,且相应地,适合于在每一种制备情况下所需的起始原料和中间体。这些基团定义可以相互间按需要组合,即,包括给定的优选范围间的组合。
新颖的通式(I)的取代的N-氰基脒类具有令人感兴趣的生物性能。特别是,它们具有强的除草活性。
新颖的通式(I)的取代的N-氰基脒如下获得:任选地在反应辅助剂存在下和在稀释剂存在下,使通式(II)的N-氰基-亚氨酸酯与通式(III)的氨基化合物反应,其中R1如上文所定义,且R’代表烷基,其中R2如上定义。
使用例如N-氰基-丙亚胺酸乙酯和吲哚-2-基-胺作为起始原料,本发明方法中的反应过程可以用下列反应式来说明:式(II)提供在制备通式(I)化合物的本发明方法中用作起始原料的N-氰基-亚胺酸酯的一般定义。在式(II)中,R1优选具有在上文有关本发明式(I)化合物的描述中业已提到的R1的优选、特别优选、非常特别优选或最优选的含义;R’优选代表具有1至4个碳原子的烷基,特别是甲基或乙基。
通式(II)的N-氰基-亚胺酸酯是已知的和/或可以用本身已知的方法制备(参见,例如,J.Am.Chem.Soc.104(1982),235-239;同前,106(1984),2805-2811;J.Org.Chem.28(1963),1816-1821;同前,46(1981),1457-1465;合成[Synthesis]1983,402-404;四面体通讯[Tetrahedron Lett.]21(1980),909-912)。
式(III)提供在制备式(I)化合物的本发明方法中另一用作起始原料的氨基化合物的一般定义。在式(III)中,R2优选具有在上文有关本发明式(I)化合物的描述中业已提到的R2的优选、特别优选、非常特别优选或最优选的含义。
通式(III)的起始原料是已知的和/或可以通过本身已知的方法制备(参见,J.Am.Chem.Soc.88(1966),2233-2240;同前,95(1973),4083-4084);J.Chem.Soc.C 1966,717-722;合成[Synthesis]1980,695-697;四面体[Tetrahedron]24(1968),3681-3696;同前50(1994),3627-3638)。
任选地,制备通式(I)化合物的本发明方法是使用反应辅助剂进行的。适合于本发明方法的反应辅助剂通常是所有的常规无机或有机碱或酸受体。优选的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、氢氧化物或醇盐,例如,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、甲醇钠、乙醇钠、正或异丙醇钠、正-、异-、仲-或叔丁醇钠、甲醇钾、乙醇钾、正或异丙醇钾、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-二异丙基胺、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-、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]十一-7-烯(DBU)。
在大多数情况下,可以省去上面提到的反应辅助剂之一的使用。
制备通式(I)化合物的本发明方法优选使用稀释剂进行。适合稀释剂,除了水之外,特别是惰性有机溶剂。这些溶剂优选包括脂肪族、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、丁酮或甲基异丁基酮;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;以及亚砜类,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、二甘醇单甲醚、二甘醇单乙醚,它们与水的混合物或纯水。
进行本发明方法时,反应温度可以在较宽的范围内进行的。通常,反应是在0℃至150℃,优选在10℃至120℃间的温度下进行。
本发明的方法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、任选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数小时。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、蔊菜属、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、山羊草属、虉草属,
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。
取决于其浓度,本发明的活性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,活性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)化合物当施于土壤或用于植物地上部分时,具有强的除草活性和宽阔的活性谱;在某种程度上,它们还适合于以芽前和芽后二种方式选择性地防治单子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、粉尘剂、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,即液体溶剂和/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。
如果用水作扩充剂,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,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。其它可能的添加剂是矿物油和植物油。
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,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、benzobicyclon、吡草酮、新燕灵(乙酯)、双丙氨酰磷、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、草灭畏、杀草敏、氯嘧黄隆(乙酯)、草枯醚、绿黄隆、绿麦隆、cinidon(-ethyl)、环庚草醚、醚黄隆、clefoxydim、烯草酮、炔草酸、异噁草酮、氯甲酰草胺、二氯吡啶酸、clopyrasulfuron(-ethyl)、cloransulam(-methyl)、cumyluron、氰草津、cybutryne、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(甲酯)、diclosulam、乙酰甲草胺、野燕枯、吡氟草胺、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、杀草隆、epoprodan、茵达灭、戊草丹、乙丁烯氟灵、胺苯黄隆(甲酯)、乙呋草黄、ethoxyfen、ethoxysulfuron、etobenzanid、噁唑禾草灵乙酯、fentrazamide、麦草伏(异丙酯)、麦草伏(异丙酯-L)、麦草伏(甲酯)、啶嘧黄隆、florasulam、吡氟禾草灵(丁酯)、fluazolate、flucarbazone、flufenacet、唑嘧磺草胺、氟烯草酸、丙炔氟草胺、flumipropyn、吡唑磺草胺、氟草隆、氟咯草隆、乙羧氟草醚(乙酯)、胺草唑、flupropacil、flupyrasulfuron(-methyl、sodium)、芴丁酸、氟啶草酮、氯氟吡氧乙酸、氟嘧醇、flurtamone、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)、精吡氟氯禾灵(甲酯)、环嗪酮、咪草酯(甲酯)、imazamethapyr、imazamox、imazapic、灭草烟、灭草喹、咪草烟、咪唑黄隆、碘磺隆(甲酯,钠盐)、碘苯腈、异丙乐灵、异丙隆、异噁隆、异噁酰草胺、isoxachlortole、isoxaflutole、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、mesotrione、苯嗪草酮、吡唑草胺、甲基苯噻隆、吡喃隆、秀谷隆、(α-)异丙甲草胺、磺草唑胺、甲氧隆、嗪草酮、甲黄隆(甲酯)、草达灭、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、壬酸、二甲戊灵、pendralin、pentoxazone、甜菜宁、哌草磷、丙草胺、氟嘧黄隆(甲酯)、扑草净、毒草胺、敌稗、喔草酯、异丙草胺、戊炔草胺、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、喹草酸、灭藻醌、喹禾灵(乙酯)、喹禾灵(四氢糠酯)、砜嘧黄隆、稀禾定、西玛津、西草净、sulcitrione、甲磺草胺、嘧黄隆(甲酯)、草锍磷、甲嘧磺隆、牧草胺、特丁噻草隆、tepraloxydim、特丁津、特丁净、噻吩草胺、噻呋酰胺、噻唑烟酸、thidiazimin、噻黄隆(甲酯)、杀草丹、仲草丹、肟草酮、野燕畏、醚苯黄隆、苯黄隆(甲酯)、绿草定、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10千克之间,优选每公顷5克至5千克。
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:
在室温(大约20℃)下,将0.98g(10mmol)N-氰基-乙亚胺酸甲酯、1.42g(10mmol)1,2,3,4-四氢-1-萘基胺和20ml水的混合物搅拌12小时。随后通过抽吸过滤分离出所得的晶状产物,用少量水和乙醚洗涤,并在陶土制成的盘中干燥。
由此给出1.3g(理论值的62%)N’-氰基-(1,2,3,4-四氢-1-萘基)-乙亚胺酰胺,熔点113℃。
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%=完全破坏
在此试验中,例如,制备实施例1化合物对杂草显示出非常强的活性。
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1化合物对杂草显示出非常强的活性。
Claims (8)
2.根据权利要求1的化合物,其特征在于,R1 代表氢,代表任选由氰基-、卤素-、C1-C4-烷氧基-、C1-C4-烷硫基-、C1-C4-烷基亚磺酰基-或C1-C4-烷基磺酰基-取代的具有1至6个碳原子的烷基,代表各任选由卤素-取代的各具有2至6个碳原子的烯基或炔基,代表各任选由氰基-、卤素-或C1-C4-烷基-取代的在环烷基中各具有3至6个碳原子和任选在烷基部分具有1至4个碳原子的环烷基或环烷基烷基,或代表各任选由硝基-、氰基-、卤素-、C1-C4-烷基-、C1-C4-卤代烷基-、C1-C4-烷氧基-或C1-C4-卤代烷氧基-取代的在芳基部分各具有6或10个碳原子和任选在烷基部分具有1至4个碳原子的芳基或芳烷基,代表选自下文所列的各自苯并稠合的、吡啶并稠合的或噻吩并稠合的环烷(烯)基、氧杂环烷(烯)基或硫杂环烷(烯)基:其中所有的环状或杂环状基团可以优选由下文所列基团之一取代:硝基、羟基、氨基、氰基、氨基甲酰基、硫代氨基甲酰基、甲酰基氨基、卤素、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷硫基、C1-C4-卤代烷硫基、C1-C4-烷基亚磺酰基、C1-C4-卤代烷基亚磺酰基、C1-C4-烷基磺酰基、C1-C4-卤代烷基磺酰基、C1-C4-烷基氨基、二-(C1-C4-烷基)-氨基、C1-C4-烷基-羰基、C1-C4-烷氧基-羰基、C1-C4-烷基氨基-羰基、二-(C1-C4-烷基)-氨基-羰基、C1-C4-烷基-羰基-氨基、C1-C4-烷氧基-羰基-氨基、C1-C4-烷基-氨基-羰基-氨基、C1-C4-烷基-磺酰基-氨基。
3.根据权利要求1或2的化合物,其特征在于R1 代表氢,代表各任选由氰基-、氟-、氯-、溴-、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-、正或异丙基亚磺酰基-、甲基磺酰基-、乙基磺酰基-、正或异丙基磺酰基取代的甲基、乙基、正或异丙基、正-、异-、仲-或叔丁基,代表各任选由氟-、氯-或溴-取代的乙烯基、丙烯基、丁烯基、乙炔基、丙炔基或丁炔基,代表各任选由氰基-、氟-、氯-、溴-、甲基-、乙基-、正或异丙基-取代的环丙基、环丁基、环戊基、环己基、环丙基甲基、环丁基甲基、环戊基甲基或环己基甲基,或代表各任选由硝基-、氰基-、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-、二氟甲氧基-或三氟甲氧基-取代的苯基或苄基,和R2 代表权利要求1或2中提到的环状或杂环状基团之一,其中取代基可以选自下文所列的基团之一:硝基、羟基、氨基、氰基、氨基甲酰基、硫代氨基甲酰基、甲酰基氨基、氟、氯、溴、甲基、乙基、正或异丙基、正、异、仲或叔丁基、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、甲氧基、乙氧基、正或异丙氧基、二氟甲氧基、三氟甲氧基、氯二氟甲氧基、氟二氯甲氧基、甲硫基、乙硫基、正或异丙硫基、二氟甲硫基、三氟甲硫基、氯二氟甲硫基、氟二氯甲硫基、甲基亚磺酰基、乙基亚磺酰基、三氟甲基亚磺酰基、甲基磺酰基、乙基磺酰基、三氟甲基磺酰基、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、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、二甲基氨基羰基、二乙基氨基羰基、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、甲基氨基羰基氨基、乙基氨基羰基氨基、正或异丙基氨基羰基氨基、甲基磺酰基氨基、乙基磺酰基氨基、正或异丙基磺酰基氨基。
4.根据权利要求1至3之任一项的化合物,其特征在于R1 代表氢或代表各任选由氰基-、氟-、氯-、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-取代的甲基、乙基、正或异丙基,和R2 代表列于下文的苯并稠合的环烷(烯)基:
其中所有的环状基团可以由下文所列的基团之一取代:硝基、羟基、氨基、氰基、氨基甲酰基、硫代氨基甲酰基、甲酰基氨基、氟、氯、溴、甲基、乙基、正或异丙基、正、异、仲或叔丁基、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、甲氧基、乙氧基、正或异丙氧基、二氟甲氧基、三氟甲氧基、氯二氟甲氧基、氟二氯甲氧基、甲硫基、乙硫基、正或异丙硫基、二氟甲硫基、三氟甲硫基、氯二氟甲硫基、氟二氯甲硫基、甲基亚磺酰基、乙基亚磺酰基、三氟甲基亚磺酰基、甲基磺酰基、乙基磺酰基、三氟甲基磺酰基、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、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、二甲基氨基羰基、二乙基氨基羰基、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、甲基氨基羰基氨基、乙基氨基羰基氨基、正或异丙基氨基羰基氨基、甲基磺酰基氨基、乙基磺酰基氨基、正或异丙基磺酰基氨基。
5.根据权利要求1至4之任一项的化合物,其特征在于R1 代表氢、甲基、乙基或正或异丙基,R2 代表下文的基团之一
6.制备权利要求1至5之任一项的化合物的方法,其特征在于,任选地在反应辅助剂存在下和任选地在稀释剂存在下,使通式(II)的N-氰基亚胺酸酯与通式(III)的氨基化合物反应,其中R1 如权利要求1至5之任一项中所定义,且R2 代表烷基,其中R2 如权利要求1至5之任一项中所定义。
7.除草组合物,其特征在于,它们包含至少一种权利要求1至5之任一项的化合物和常规的扩充剂。
8.权利要求1至5之任一项的至少一种化合物防治不希望的植物的应用。
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DE19921886A DE19921886A1 (de) | 1999-05-12 | 1999-05-12 | Substituierte N-Cyano-amidine |
DE19921886.2 | 1999-05-12 |
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KR (1) | KR20020005008A (zh) |
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CA (1) | CA2373429A1 (zh) |
DE (1) | DE19921886A1 (zh) |
HK (1) | HK1044530A1 (zh) |
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CN102459158A (zh) * | 2009-04-20 | 2012-05-16 | 雅培制药有限公司 | 新的酰胺和脒衍生物和其用途 |
CN106146349A (zh) * | 2015-04-07 | 2016-11-23 | 中国科学院大连化学物理研究所 | 一种芳香醛催化转化制备脒的方法 |
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US4661520A (en) * | 1984-08-17 | 1987-04-28 | The Dow Chemical Company | Cyanoguanidine useful as an animal growth promoting agent |
US4684398A (en) * | 1984-08-17 | 1987-08-04 | The Dow Chemical Company | Herbicidal cyanoguanidines and cyanoisothioureas |
GB8630759D0 (en) * | 1986-12-23 | 1987-02-04 | Janssen Pharmaceutica Nv | Carboxylic acid derivatives |
EP0314852B1 (de) * | 1987-11-06 | 1993-11-18 | Ciba-Geigy Ag | Verfahren zur Synthese von 1-substituierten Imidazol-5-carbonsäuren und -carbonsäure-derivaten |
EP0347378A1 (de) * | 1988-06-13 | 1989-12-20 | Ciba-Geigy Ag | Imidazol-Derivate |
US5104890A (en) * | 1989-03-28 | 1992-04-14 | Fujisawa Pharmaceutical Company, Ltd. | Benzopyran derivatives and processes for preparation thereof |
US5095016A (en) * | 1989-08-11 | 1992-03-10 | Kaken Pharmaceutical Co., Ltd. | Benzopyran compounds, processes for their production and pharmaceutical compositions |
WO1995002589A1 (fr) * | 1993-07-16 | 1995-01-26 | Japan Tobacco Inc. | Nouveau compose du chromane, ses intermediaires et ses applications medicinales |
DE19924273A1 (de) * | 1998-07-18 | 2000-01-20 | Bayer Ag | Imidamid-Derivate |
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CN102459158A (zh) * | 2009-04-20 | 2012-05-16 | 雅培制药有限公司 | 新的酰胺和脒衍生物和其用途 |
CN103772239A (zh) * | 2009-04-20 | 2014-05-07 | Abbvie公司 | 新的酰胺和脒衍生物和其用途 |
CN102459158B (zh) * | 2009-04-20 | 2015-11-25 | Abbvie公司 | 新的酰胺和脒衍生物和其用途 |
CN103772239B (zh) * | 2009-04-20 | 2017-04-12 | Abbvie 公司 | 酰胺和脒衍生物和其用途 |
CN106146349A (zh) * | 2015-04-07 | 2016-11-23 | 中国科学院大连化学物理研究所 | 一种芳香醛催化转化制备脒的方法 |
CN106146349B (zh) * | 2015-04-07 | 2018-02-13 | 中国科学院大连化学物理研究所 | 一种芳香醛催化转化制备脒的方法 |
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EP1178956A1 (de) | 2002-02-13 |
WO2000069813A1 (de) | 2000-11-23 |
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HK1044530A1 (zh) | 2002-10-25 |
AU765922B2 (en) | 2003-10-02 |
DE19921886A1 (de) | 2000-11-16 |
CA2373429A1 (en) | 2000-11-23 |
AU4755300A (en) | 2000-12-05 |
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KR20020005008A (ko) | 2002-01-16 |
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