CN1316989A - 旋光的取代的n-芳基-o-芳氧基烷基-氨基甲酸酯类 - Google Patents
旋光的取代的n-芳基-o-芳氧基烷基-氨基甲酸酯类 Download PDFInfo
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- CN1316989A CN1316989A CN99810513A CN99810513A CN1316989A CN 1316989 A CN1316989 A CN 1316989A CN 99810513 A CN99810513 A CN 99810513A CN 99810513 A CN99810513 A CN 99810513A CN 1316989 A CN1316989 A CN 1316989A
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- phenyl
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- ethyl
- methyl
- alkyl
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- -1 isochinolinyl Chemical group 0.000 claims abstract description 243
- 150000001875 compounds Chemical class 0.000 claims abstract description 45
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 25
- 238000000034 method Methods 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 15
- 150000002367 halogens Chemical group 0.000 claims abstract description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 6
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 6
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims abstract description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims abstract description 4
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 4
- 125000002541 furyl group Chemical group 0.000 claims abstract description 4
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 4
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims abstract description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 3
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims abstract description 3
- 241000196324 Embryophyta Species 0.000 claims description 30
- 238000002360 preparation method Methods 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 239000011737 fluorine Substances 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 150000001721 carbon Chemical group 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 7
- 239000000203 mixture Substances 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
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 6
- 230000002363 herbicidal effect Effects 0.000 claims description 6
- 229950001891 iprotiazem Drugs 0.000 claims description 6
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 6
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 6
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 239000002689 soil Substances 0.000 claims description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 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 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims description 4
- 150000004982 aromatic amines Chemical class 0.000 claims description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 3
- 125000005493 quinolyl group Chemical group 0.000 claims description 3
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 3
- ZRNSSRODJSSVEJ-UHFFFAOYSA-N 2-methylpentacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(C)C ZRNSSRODJSSVEJ-UHFFFAOYSA-N 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 claims description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 125000006309 butyl amino group Chemical group 0.000 claims description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 2
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 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
- 239000011630 iodine Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 2
- NBVXSUQYWXRMNV-UHFFFAOYSA-N monofluoromethane Natural products FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 2
- JVJQPDTXIALXOG-UHFFFAOYSA-N nitryl fluoride Chemical compound [O-][N+](F)=O JVJQPDTXIALXOG-UHFFFAOYSA-N 0.000 claims description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 241000405414 Rehmannia Species 0.000 claims 1
- 239000004009 herbicide Substances 0.000 abstract description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 3
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 abstract 1
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 abstract 1
- 125000002619 bicyclic group Chemical group 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000002950 monocyclic group Chemical group 0.000 abstract 1
- 230000010287 polarization Effects 0.000 abstract 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 abstract 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 abstract 1
- 239000002994 raw material Substances 0.000 description 13
- 150000004702 methyl esters Chemical class 0.000 description 11
- 244000025254 Cannabis sativa Species 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 230000000694 effects Effects 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 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 7
- 239000002904 solvent Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 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
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 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
- 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
- 150000001412 amines Chemical class 0.000 description 4
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- 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
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- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
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- 229960000278 theophylline Drugs 0.000 description 1
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- 229930192474 thiophene Natural products 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 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
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-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
- 238000009834 vaporization Methods 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
- 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
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- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
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- A01N47/20—N-Aryl derivatives thereof
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- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
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- C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
- C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
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Abstract
本发明涉及新颖的通式(Ⅰ)的旋光的取代的N芳基-O-芳氧基烷基-氨基甲酸酯类,其中Ar1代表选自下列的任选被取代的单环状或双环状碳环或杂环基:苯基、萘基、四氢化萘基、呋喃基、苯并呋喃基、噻吩基、苯并噻吩基、吡啶基、喹啉基、异喹啉基或是同样任选被取代的基团(a),其中A代表任选由卤素取代的具有1至3个碳原子的链烷二基,且其中在每一种情况下可能的取代基优选选自下列:氰基、硝基、卤素、各任选由卤素取代的各具有至多5个碳原子的烷基、烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷基羰基、烷氧基羰基;Ar2代表具有6至10个碳原子的芳基,该芳基任选由硝基、氰基、羧基、氨基甲酰基、硫代氨基甲酰基、卤素,或由(各任选由氰基-、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)各在烷基中具有至多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、二烷基氨基、烷基羰基、烷氧基羰基、烷基氨基羰基或二烷基氨基羰基取代,R1代表任选由氰基-、卤素-或C1-C4-烷氧基-取代的具有1至4个碳原子的烷基,和R2代表氢或任选由氰基-、卤素-或C1-C4-烷氧基-取代的具有1至4个碳原子的烷基,其条件是,在通式(Ⅰ)化合物中,在R1连接的碳原子上的取代基如此排列,使偏振光的震动平面向左旋转。本发明还涉及其制备方法以及其作为除草剂的应用。
Description
本发明涉及新颖的旋光的取代的N-芳基-O-芳氧基烷基-氨基甲酸酯类化合物,涉及其制备及其作为除草剂的应用。
业已知道某些取代的N-芳基-O-芳氧基烷基-氨基甲酸酯类具有除草性能(参见,例如,US-A 5 099 059、US-A 5 152 827、US-A 5194 661)。然而,这些化合物的性能并非在所有方面均令人满意。
Ar1代表各任选被取代的选自下列的单环状或双环状碳环或杂环基:
苯基、萘基、四氢化萘基、呋喃基、苯并呋喃基、噻吩基、苯并噻吩基、吡啶基、喹啉基、异喹啉基,或是同样任选被取代的下列基团:其中A代表任选由卤素取代的具有1至3个碳原子的链烷二基,且其中在每一种情况下可能的取代基优选选自下列:
氰基、硝基、卤素、各任选由卤素取代的各具有至多5个碳原子的烷基、烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷基羰基、烷氧基羰基,
Ar2代表具有6至10个碳原子的芳基,该芳基任选由硝基、氰基、羧基、氨基甲酰基、硫代氨基甲酰基、卤素,或由(各任选由氰基-、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)各在烷基中具有至多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、二烷基氨基、烷基羰基、烷氧基羰基、烷基氨基羰基或二烷基氨基羰基取代,
R1代表任选由氰基-、卤素-或C1-C4-烷氧基-取代的具有1至4个碳原子的烷基,和
R2代表氢或任选由氰基-、卤素-或C1-C4-烷氧基-取代的具有1至4个碳原子的烷基,
其条件是,在通式(Ⅰ)化合物中,在R1连接的碳原子上的取代基如此排列,使偏振光的震动平面向左旋转,即,式(Ⅰ)化合物为(-)对映体。
在定义中,烃链如烷基,各可以是直链或支链--包括与杂原子的组合如在烷氧基中。
Ar1优选代表上面提到基团之一,其中A代表各任选由氟-和/或氯-取代的亚甲基或二亚甲基(乙-1,2-二基),且其中每一种情况下可能的取代基优选自下列:
氰基、硝基、氟、氯、溴、各任选由氟-和/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、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、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、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。
Ar2优选代表苯基或萘基,它们各任选由下列基团取代:
硝基、氰基、羧基、氨基甲酰基、硫代氨基甲酰基、氟、氯、溴、碘、或(各任选由氰基-、氟-、氯-、甲氧基-、乙氧基-、甲硫基-、乙硫基-、甲基亚磺酰基-、乙基亚磺酰基-、甲基磺酰基-或乙基磺酰基-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、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、甲基氨基、乙基氨基、正或异丙基氨基、正-、异-、仲-或叔丁基氨基、二甲基氨基、二乙基氨基、乙酰基、丙酰基、正或仲丁酰基、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、二甲基氨基羰基或二乙基氨基羰基。
R1优选代表甲基、乙基、正或异丙基。
R2优选代表氢、甲基、乙基、正或异丙基。
Ar1特别优选代表苯基,它在3位上含有一个选自下列的取代基:氰基、硝基、氟、氯、溴、甲基、乙基、正或异丙基、氯甲基、氟甲基、二氯甲基、二氟甲基、三氯甲基、三氟甲基、甲氧基、乙氧基、氟甲氧基、二氟甲氧基、氯氟甲氧基、三氟甲氧基、氯二氟甲氧基,和任选地在另一位置上含有另外一个上面所列的取代基。
Ar2特别优选代表苯基,它任选由下列基团取代:硝基、氰基、氟、氯、溴、或(各任选由氟-和/或氯-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、正或异丙基磺酰基、甲基磺酰基、乙基磺酰基、正或异丙基磺酰基、二甲基氨基、乙酰基、丙酰基、甲氧基羰基、乙氧基碳基或二甲基氨基羰基。
R1特别优选代表甲基或乙基。
R2特别优选代表氢、甲基或乙基。
本发明优选的是含有上面所列优选含义组合的化合物。
本发明特别优选的是含有上面所列特别优选含义组合的化合物。
列于上文中的一般或优选的基团定义适合于式(Ⅰ)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,包括优选化合物给定的范围间的组合。
在此,Ar2具有,例如,下文给出的含义:
2-氯-3-氟-苯基,2,3-二氯-苯基,2-氯-3-溴-苯基,2-氯-3-甲基-苯基,2-氯-3-乙基-苯基,2-氯-3-三氟甲基-苯基,2-氯-3-氰基-苯基,2-氯-3-甲氧基-苯基,2-氯-3-乙氧基-苯基,2-氯-4-氟-苯基,2,4-二氯-苯基,2-氯-4-溴-苯基,2-氯-4-甲基-苯基,2-氯-4-乙基-苯基,2-氯-4-三氟甲基-苯基,2-氯-4-氰基-苯基,2-氯-4-甲氧基-苯基,2-氯-4-乙氧基-苯基,2-氯-5-氟-苯基,2,5-二氯-苯基,2-氯-5-溴-苯基,2-氯-5-甲基-苯基,2-氯-5-乙基-苯基,2-氯-5-三氟甲基-苯基,2-氯-5-氰基-苯基,2-氯-5-甲氧基-苯基,2-氯-5-乙氧基-苯基,2-氯-6-氟-苯基,2,6-二氯-苯基,2-氯-6-溴-苯基,2-氯-6-甲基-苯基,2-氯-6-乙基-苯基,2-氯-6-三氟甲基-苯基,2-氯-6-氰基-苯基,2-氯-6-甲氧基-苯基,2-氯-6-乙氧基-苯基;
2,3-二氟-苯基,2-氟-3-氯-苯基,2-氟-3-溴-苯基,2-氟-3-甲基-苯基,2-氟-3-乙基-苯基,2-氟-3-三氟甲基-苯基,2-氟-3-氰基-苯基,2-氟-3-甲氧基-苯基,2-氟-3-乙氧基-苯基,2,4-二氟-苯基,2-氟-4-氯-苯基,2-氟-4-溴-苯基,2-氟-4-甲基-苯基,2-氟-4-乙基-苯基,2-氟-4-三氟甲基-苯基,2-氟-4-氰基-苯基,2-氟-4-甲氧基-苯基,2-氟-4-乙氧基-苯基,2,5-二氟-苯基,2-氟-5-氯-苯基,2-氟-5-溴-苯基,2-氟-5-甲基-苯基,2-氟-5-乙基-苯基,2-氟-5-三氟甲基-苯基,2-氟-5-氰基-苯基,2-氟-5-甲氧基-苯基,2-氟-5-乙氧基-苯基,2,6-二氟-苯基,2-氟-6-氯-苯基,2-氟-6-溴-苯基,2-氟-6-甲基-苯基,2-氟-6-乙基-苯基,2-氟-6-三氟甲基-苯基,2-氟-6-氰基-苯基,2~氟-6-甲氧基-苯基,2-氟-6-乙氧基-苯基;
2-溴-3-氟-苯基,2-溴-3-氯-苯基,2,3-二溴-苯基,2-溴-3-甲基-苯基,2-溴-3-乙基-苯基,2-溴-3-三氟甲基-苯基,2-溴-3-氰基-苯基,2-溴-3-甲氧基-苯基,2-溴-3-乙氧基-苯基,2-溴-4-氟-苯基,2-溴-4-氯-苯基,2,4-二溴-苯基,2-溴-4-甲基-苯基,2-溴-4-乙基-苯基,2-溴-4-三氟甲基-苯基,2-溴-4-氰基-苯基,2-溴-4-甲氧基-苯基,2-溴-4-乙氧基-苯基,2-溴-5-氟-苯基,2-溴-5-氯-苯基,2,5-二溴-苯基,2-溴-5-甲基-苯基,2-溴-5-乙基-苯基,2-溴-5-三氟甲基-苯基,2-溴-5-氰基-苯基,2-溴-5-甲氧基-苯基,2-溴-5-乙氧基-苯基,2-溴-6-氟-苯基,2-溴-6-氯-苯基,2-溴-6-溴-苯基,2-溴-6-甲基-苯基,2-溴-6-乙基-苯基,2-溴-6-三氟甲基-苯基,2-溴-6-氰基-苯基,2-溴-6-甲氧基-苯基,2-溴-6-乙氧基-苯基;
2-甲基-3-氟-苯基,2-甲基-3-氯-苯基,2-甲基-3-溴-苯基,2,3-二甲基-苯基,2-甲基-3-乙基-苯基,2-甲基-3-三氟甲基-苯基,2甲基-3-氰基-苯基,2-甲基-3-甲氧基-苯基,2-甲基-3-乙氧基-苯基,2-甲基-4-氟-苯基,2-甲基-4-氯-苯基-,2-甲基-4-溴-苯基,2,4-二甲基-苯基,2-甲基-4-乙基-苯基,2-甲基-4-三氟甲基-苯基,2-甲基-4-氰基-苯基,2-甲基-4-甲氧基-苯基,2-甲基-4-乙氧基-苯基,2-甲基-5-氟-苯基,2-甲基-5-氯-苯基,2-甲基-5-溴-苯基,2,5-二甲基-苯基,2-甲基-5-乙基-苯基,2-甲基-5-三氟甲基-苯基,2-甲基-5-氰基-苯基,2-甲基-5-甲氧基-苯基,2-甲基-5-乙氧基-苯基,2-甲基-6-氟-苯基,2-甲基-6-氯-苯基,2-甲基-6-溴-苯基,2,6-二甲基-苯基,2-甲基-6-乙基-苯基,2-甲基-6-三氟甲基-苯基,2甲基-6-氰基-苯基,2-甲基-6-甲氧基-苯基,2-甲基-6-乙氧基-苯基;
2-乙基-3-氟-苯基,2-乙基-3-氯-苯基,2-乙基-3-溴-苯基,2-乙基-3-甲基-苯基,2,3-二乙基-苯基,2-乙基-3-三氟甲基-苯基,2-乙基-3-氰基-基基,2-乙基-3-甲氧基-苯基,2-乙基-3-乙氧基-苯基,2-乙基-4-氟苯基,2-乙基-4-氯-苯基,2-乙基-4-溴-苯基,2-乙基-4-甲基-苯基,2,4-二乙基-苯基,2-乙基-4-三氟甲基-苯基,
2-乙基-4-氰基-苯基,2-乙基-4-甲氧基-苯基,2-乙基-4-乙氧基-苯基,2-乙基-5-氟-苯基,2-乙基-5-氯-苯基,2-乙基-5-溴-苯基,2-乙基-5-甲基苯基,2,5-二乙基-苯基,2-乙基-5-三氟甲基-苯基,2-乙基-5-氰基-苯基,2-乙基-5-甲氧基-苯基,2-乙基-5-乙氧基-苯基,2-乙基-6-氟-苯基,2-乙基-6-氯-苯基,2-乙基-6-溴-苯基,2-乙基-6-甲基-苯基,2,6-二乙基苯基,2-乙基-6-三氟甲基-苯基,2-乙基-6-氰基-苯基,2-乙基-6-甲氧基-苯基,2-乙基-6-乙氧基-苯基;
2-三氟甲基-3-氟-苯基,2-三氟甲基-3-氯-苯基,2-三氟甲基-3-溴-苯基,2-三氟甲基-3-甲基-苯基,2-三氟甲基-3-乙基-苯基,2,3-双-三氟甲基-苯基,2-三氟甲基-3-氰基-苯基,2-三氟甲基-3-甲氧基-苯基,2-三氟甲基-3-乙氧基-苯基,2-三氟甲基-4-氟-苯基,2-三氟甲基-4-氯-苯基,2-三氟甲基-4-溴-苯基,2-三氟甲基-4-甲基-苯基,2-三氟甲基-4-乙基-苯基,2,4-双-三氟甲基-苯基,2-三氟甲基-4-氰基-苯基,2-三氟甲基-4-甲氧基-苯基,2-三氟甲基-4-乙氧基-苯基,2-三氟甲基-5-氟-苯基,2-三氟甲基-5-氯-苯基,2-三氟甲基-5-溴-苯基,2-三氟甲基-5-甲基-苯基,2-三氟甲基-5-乙基-苯基,2,5-双三氟甲基-苯基,2-三氟甲基-5-氰基-苯基,2-三氟甲基-5-甲氧基-苯基,2-三氟甲基-5-乙氧基-苯基,2-三氟甲基-6-氟-苯基,2-三氟甲基-6-氯-苯基,2-三氟甲基-6-溴-苯基,2-三氟甲基-6-甲基-苯基,2-三氟甲基-6-乙基-苯基,2,6-双-三氟甲基-苯基,2-三氟甲基-6-氰基-苯基,2-三氟甲基-6-甲氧基-苯基,2-三氟甲基-6-乙氧基-苯基;
2-氰基-3-氟-苯基,2-氰基-3-氯-苯基,2-氰基-3-溴-苯基,2-氰基-3-甲基-苯基,2-氰基-3-乙基-苯基,2-氰基-3-三氟甲基-苯基,2,3-二氰基-苯基,2-氰基-3-甲氧基-苯基,2-氰基-3-乙氧基-苯基,2-氰基-4-氟-苯基,2-氰基-4-氯-苯基,2-氰基-4-溴-苯基,2-氰基-4-甲基-苯基,2-氰基-4-乙基-苯基,2-氰基-4-三氟甲基-苯基,2,4-二氰基-苯基,2-氰基-4-甲氧基-苯基,2-氰基-4-乙氧基-苯基,2-氰基-5-氟-苯基,2-氰基-5-氯-苯基,2-氰基-5-溴-苯基,2-氰基-5-甲基-苯基,2-氰基-5-乙基-苯基,2-氰基-5-三氟甲基-苯基,2,5-二氰基苯基,2-氰基-5-甲氧基-苯基,2-氰基-5-乙氧基-苯基,2-氰基-6-氟-苯基,2-氰基-6-氯-苯基,2-氰基-6-溴-苯基,2-氰基-6-甲基-苯基,2氰基-6-乙基-苯基,2-氰基-6-三氟甲基-苯基,2-氰基-6-氰基-苯基,2-氰基-6-甲氧基-苯基,2-氰基-6-乙氧基-苯基;
2-甲氧基-3-氟-苯基,2-甲氧基-3-氯-苯基,2-甲氧基-3-溴-苯基,2-甲氧基-3-甲基-苯基,2-甲氧基-3-乙基-苯基,2-甲氧基-3-三氟甲基-苯基,2-甲氧基-3-氰基-苯基,2,3-二甲氧基-苯基,2-甲氧基-3-乙氧基-苯基,2-甲氧基-4-氟-苯基,2-甲氧基-4-氯-苯基,2-甲氧基-4-溴-苯基,2-甲氧基-4-甲基-苯基,2-甲氧基-4-乙基-苯基,2-甲氧基-4-三氟甲基-苯基,2-甲氧基-4-氰基-苯基,2,4-二甲氧基-苯基,2-甲氧基-4-乙氧基-苯基,2-甲氧基-5-氟-苯基,2-甲氧基-5-氯-苯基,2-甲氧基-5-溴-苯基,2-甲氧基-5-甲基-苯基,2-甲氧基-5-乙基-苯基,2-甲氧基-5-三氟甲基-苯基,2-甲氧基5-氰基-苯基,2,5-二甲氧基-苯基,2-甲氧基-5-乙氧基-苯基,2-甲氧基-6-氟-苯基,2-甲氧基-6-氯-苯基,2-甲氧基-6-溴-苯基,2-甲氧基-6-甲基-苯基,2-甲氧基-6-乙基-苯基,2-甲氧基-6-三氟甲基-苯基,2-甲氧基-6-氰基-苯基,2,6-二甲氧基-苯基,2-甲氧基-6-乙氧基-苯基;
2-乙氧基-3-氟-苯基,2-乙氧基-3-氯-苯基,2-乙氧基-3-溴-苯基,2-乙氧基-3-甲基-苯基,2-乙氧基-3-乙基-苯基,2-乙氧基-3-三氟甲基-苯基,2-乙氧基-3-氰基-苯基,2-乙氧基-3-甲氧基-苯基,2,3-二乙氧基-苯基,2-乙氧基-4-氟-苯基,2-乙氧基-4-氯-苯基,2-乙氧基-4-溴-苯基,2-乙氧基-4-甲基-苯基,2-乙氧基-4-乙基-苯基,2-乙氧基-4-三氟甲基-苯基,2-乙氧基-4-氰基-苯基,2-乙氧基-4-甲氧基-苯基,2,4-二乙氧基-苯基,2-乙氧基5-氟-苯基,2-乙氧基-5-氯-苯基,2-乙氧基-5-溴-苯基,2-乙氧基-5甲基-苯基,2-乙氧基-5-乙基-苯基,2-乙氧基-5-三氟甲基-苯基,2-乙氧基-5-氰基-苯基,2-乙氧基-5-甲氧基-苯基,2,5-二乙氧基-苯基,2-乙氧基-6-氟-苯基,2-乙氧基-6-氯-苯基,2-乙氧基-6-溴-苯基,2-乙氧基-6-甲基-苯基,2-乙氧基-6-乙基-苯基,2-乙氧基-6-三氟甲基-苯基,2-乙氧基-6-氰基-苯基,2-乙氧基-6-甲氧基-苯基,2,6-二乙氧基-苯基。
组2
在此,Ar2具有,例如,上文组1中给出的含义。
在此,Ar2具有,例如,上文组1中给出的含义。
组4
在此,Ar2具有,例如,上文组1中给出的含义。
组5
在此,Ar2具有,例如,上文组1中给出的含义。
在此,Ar2具有,例如,上文组1中给出的含义。
在此,Ar2具有,例如,上文组1中给出的含义。
在此,Ar2具有,例如,上文组1中给出的含义。
在此,Ar2具有,例如,上文组1中给出的含义。
在此,Ar2具有,例如,上文组1中给出的含义。
在此,Ar2具有,例如,上文组1中给出的含义。
组12
在此,Ar2具有,例如,上文组1中给出的含义。
在此,Ar2具有,例如,上文组1中给出的含义。
组14
在此,Ar2具有,例如,上文组1中给出的含义。
组15
在此,Ar2具有,例如,上文组1中给出的含义。
在此,Ar2具有,例如,上文组1中给出的含义。
在此,Ar2具有,例如,上文组1中给出的含义。
组18
在此,Ar2具有,例如,上文组1中给出的含义。
组19
在此,Ar2具有,例如,上文组1中给出的含义。
组20
在此,Ar2具有,例如,上文组1中给出的含义。
组21
在此,Ar2具有,例如,上文组1中给出的含义。
特别优选的是带有上述前提条件的组1至3的化合物。
更特别优选的是带有上述前提条件的组2化合物。
新颖的通式(Ⅰ)的取代的N-芳基-O-烷基氨基甲酸酯显示出强的和选择性的除草作用。
新颖的通式(Ⅰ)的取代的N-芳基-O-烷基氨基甲酸酯如下获得:
(a)如果适宜在反应辅助剂存在下和如果适宜稀释剂存在下,
Ar1和R1如上定义,
或-如果R2代表氢-
Ar2如上定义,
与通式(Ⅴ)的取代的链烷醇反应其中
Ar1和R1如上定义。
使用例如(-)-氯甲酸[1-(3-甲基-苯氧基甲基)-丙基]酯和2-氟-6-甲基苯胺作为起始原料,本发明方法(a)中的反应过程可以用下列反应式来说明:
式(Ⅱ)提供在制备式(Ⅰ)化合物的本发明方法(a)中用作起始原料的芳基胺的一般定义。在式(Ⅱ)中,Ar2和R2各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Ar2和R2的优选或特别优选的含义。
通式(Ⅱ)的起始原料是合成上已知的有机化学品。
式(Ⅲ)提供在制备式(Ⅰ)化合物的本发明方法(a)中另一用作起始原料的氯甲酸酯的一般定义。在式(Ⅲ)中,Ar1和R1各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Ar1和R1的优选或特别优选的含义。
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,US-A 5 099 059,US-A 5 152 827,US-A 5 399 545)。
式(Ⅳ)提供在制备式(Ⅰ)化合物的本发明方法(b)中用作起始原料的异氰酸芳基酯的一般定义。在式(Ⅳ)中,Ar2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Ar2的优选或特别优选的含义。
通式(Ⅳ)的起始原料是合成上已知的有机化学品。
式(Ⅴ)提供在制备式(Ⅰ)化合物的本发明方法(b)中另一用作起始原料的取代的链烷醇的一般定义。在式(Ⅴ)中,Ar1和R1各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Ar1和R1的优选或特别优选的含义。
通式(V)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,US-A 5 099 059,US-A 5 152 827,US-A 5 399 545)。
适合于用在本发明方法(a)和(b)的反应辅助剂是所有的常规无机或有机碱或酸受体。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,诸如,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)。
适合于进行本发明方法(a)和(b)的稀释剂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(a)和(b)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(a)和(b)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)和(b)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、毛茛属和蒲公英属,
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、高粱属、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,本发明活性化合物可以用于防治多年生植物中的杂草,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,和用于选择性地防治一年生植物中的杂草。
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、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、烯草酮、炔草酸、异噁草酮、氯甲酰草胺、二氯吡啶酸、clopyrasulfuron(-methyl)、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、精噁唑禾草灵乙酯、麦草伏(异丙酯)、麦草伏(异丙酯-L)、麦草伏(甲酯)、啶嘧黄隆、精吡氟禾草灵(丁酯)、fluazolate、flucarbazone、flufenacet、唑嘧磺草胺、氟烯草酸、丙炔氟草胺、flumipropyn、氟草隆、氟咯草隆、乙羧氟草醚(乙酯)、胺草唑、flupropacil、flurpyrsulfuron(-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、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、二甲戊乐灵、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:
(方法(b))
在室温(大约20℃)下,将1.20g(5mmol)(-)-1-乙基-2-(3-三氟甲基-苯氧基)-乙醇、0.70g(5mmol)2,3-二甲基-苯基异氰酸酯、0.1g(10mmol)三乙胺和20ml乙腈的混合物搅拌15小时,随后仔细地在水泵真空下浓缩。残余物用石油醚消化,并将所得的晶状产物抽吸过滤分离。
由此给出1.3g(理论值的68%)(-)-N-(2,3-二甲基苯基)-0-[1-乙基-2-(3-三氟甲基-苯氧基)-乙基]-氨基甲酸酯,熔点68℃;[α]D 20=+24.8°。
类似于制备实施例1,并根据本发明制备方法的一般描述,也可以制备出例如列于下文表1中的式(Ⅰ)化合物。
实施例(Ⅴ-1)
将外消旋体分离成单个的对映体:
在室温(大约20℃)下,用HPLC(高效液体色谱)在手性固定硅胶相Chiracel OD_上,采用正庚烷与异丙醇作为移动相并使用光度计检测,将外消旋体拆分。
柱: Chiracel OD_20μm(生产厂,Daicel,日本)500*40mm
移动相:正庚烷/异丙醇(体积比10∶1)
流速: 30ml/分
检测: UV254nm
加样: 100mg外消旋体(=2.5ml的1克外消旋体在25ml移动相中的溶液)。
在分析测定对映体的纯度后,洗脱液在减压下蒸发并用作进一步反应的粗产物。
在上面提到的条件下,左旋对映体先洗脱。在20毫克/毫升的溶液浓度下,左旋对映体的旋光率为[α]D 20=-15.9(在氯仿中测定)。
用这种方式重复加载100毫克外消旋体,将所有的量分离开。
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和2化合物对杂草显示出非常强的活性,并能被作物如小麦、大麦、棉花和大豆很好地耐受。
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1和2化合物对杂草显示出非常强的活性。
Claims (7)
1.通式(Ⅰ)的取代的N-芳基-O-芳氧基烷基-氨基甲酸酯,其中
Ar1代表各任选被取代的选自下列的单环状或双环状碳环或杂环基:
苯基、萘基、四氢化萘基、呋喃基、苯并呋喃基、噻吩基、苯并噻吩基、吡啶基、喹啉基、异喹啉基,或是同样任选被取代的下列基团:其中A代表任选由卤素取代的具有1至3个碳原子的链烷二基,且其中在每一种情况下可能的取代基优选选自下列:
氰基、硝基、卤素、各任选由卤素取代的各具有至多5个碳原子的烷基、烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷基羰基、烷氧基羰基,
Ar2代表具有6至10个碳原子的芳基,该芳基任选由硝基、氰基、羧基、氨基甲酰基、硫代氨基甲酰基、卤素,或由(各任选由氰基-、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)各在烷基中具有至多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、二烷基氨基、烷基羰基、烷氧基羰基、烷基氨基羰基或二烷基氨基羰基取代,
R1代表任选由氰基-、卤素-或C1-C4-烷氧基-取代的具有1至4个碳原子的烷基,和
R2代表氢或任选由氰基-、卤素-或C1-C4-烷氧基-取代的具有1至4个碳原子的烷基,
其条件是,在通式(Ⅰ)化合物中,在R1连接的碳原子上的取代基如此排列,使偏振光的震动平面向左旋转,即,式(Ⅰ)化合物为(-)对映体。
2.根据权利要求1的取代的N-芳基-O-芳氧基烷基-氨基甲酸酯,其特征在于,
其中A代表各任选由氟-和/或氯-取代的亚甲基或二亚甲基(乙-1,2-二基),且其中每一种情况下可能的取代基优选自下列:
氰基、硝基、氟、氯、溴、各任选由氟-和/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、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、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、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,
Ar2代表苯基或萘基,它们各任选由下列基团取代:
硝基、氰基、羧基、氨基甲酰基、硫代氨基甲酰基、氟、氯、溴、碘、或(各任选由氰基-、氟-、氯-、甲氧基-、乙氧基-、甲硫基-、乙硫基-、甲基亚磺酰基-、乙基亚磺酰基-、甲基磺酰基-或乙基磺酰基-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、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、甲基氨基、乙基氨基、正或异丙基氨基、正-、异-、仲-或叔丁基氨基、二甲基氨基、二乙基氨基、乙酰基、丙酰基、正或仲丁酰基、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、二甲基氨基羰基或二乙基氨基羰基,
R1代表甲基、乙基、正或异丙基,
R2代表氢、甲基、乙基、正或异丙基。
3.根据权利要求1的取代的N-芳基-O-芳氧基烷基-氨基甲酸酯,其特征在于,
Ar1代表苯基,它在3位上含有一个选自下列的取代基:氰基、硝基、氟、氯、溴、甲基、乙基、正或异丙基、氯甲基、氟甲基、二氯甲基、二氟甲基、三氯甲基、三氟甲基、甲氧基、乙氧基、氟甲氧基、二氟甲氧基、氯氟甲氧基、三氟甲氧基、氯二氟甲氧基,和任选地在另一位置土含有另外一个上面所列的取代基,
Ar2代表苯基,它任选由下列基团取代:硝基、氰基、氟、氯、溴、或(各任选由氟-和/或氯-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、正或异丙基磺酰基、甲基磺酰基、乙基磺酰基、正或异丙基磺酰基、二甲基氨基、乙酰基、丙酰基、甲氧基羰基、乙氧基碳基或二甲基氨基羰基,
R1代表甲基或乙基,
R2代表氢、甲基或乙基。
5.防治不希望的植物的方法,其特征在于,使至少一种权利要求1至3之任一的取代的N-芳基-O-芳氧基烷基-氨基甲酸酯作用于不希望的植物和/或其栖生地。
6.至少一种权利要求1至3之任一的取代的N-芳基-O-芳氧基烷基-氨基甲酸酯防治不希望的植物的应用。
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3之任一的取代的N-芳基-O-芳氧基烷基-氨基甲酸酯。
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DE19843763.3 | 1998-09-24 | ||
DE19843763A DE19843763A1 (de) | 1998-09-24 | 1998-09-24 | Optische aktive substituierte N-Aryl-O-aryloxyalkyl-carbamate |
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CN (1) | CN1316989A (zh) |
AR (1) | AR020416A1 (zh) |
AU (1) | AU5977899A (zh) |
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CA (1) | CA2345073A1 (zh) |
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JP2002504482A (ja) * | 1998-02-20 | 2002-02-12 | バイエル・アクチエンゲゼルシヤフト | 置換アルコキシカルボニル化合物 |
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BR9914049A (pt) | 2001-06-19 |
KR20010074841A (ko) | 2001-08-09 |
AR020416A1 (es) | 2002-05-08 |
DE19843763A1 (de) | 2000-03-30 |
WO2000017157A1 (de) | 2000-03-30 |
CA2345073A1 (en) | 2000-03-30 |
JP2002526471A (ja) | 2002-08-20 |
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