CN1050873A - 取代的磺酰基脒基腙 - Google Patents
取代的磺酰基脒基腙 Download PDFInfo
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- CN1050873A CN1050873A CN90107113A CN90107113A CN1050873A CN 1050873 A CN1050873 A CN 1050873A CN 90107113 A CN90107113 A CN 90107113A CN 90107113 A CN90107113 A CN 90107113A CN 1050873 A CN1050873 A CN 1050873A
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- formula
- alkyl
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- chlorine
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- 125000004390 alkyl sulfonyl group Chemical group 0.000 title claims description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 59
- 238000002360 preparation method Methods 0.000 claims abstract description 27
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims abstract description 9
- 244000025254 Cannabis sativa Species 0.000 claims abstract description 7
- 235000010086 Setaria viridis var. viridis Nutrition 0.000 claims abstract 3
- -1 carbonyl amide acetals Chemical class 0.000 claims description 88
- 238000000034 method Methods 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 150000002431 hydrogen Chemical class 0.000 claims description 30
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 239000005864 Sulphur Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 claims description 5
- 239000013543 active substance Substances 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 4
- 239000012752 auxiliary agent Substances 0.000 claims description 4
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 150000007857 hydrazones Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 230000007480 spreading Effects 0.000 claims description 4
- 238000003892 spreading Methods 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 3
- 150000001345 alkine derivatives Chemical class 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 244000304962 green bristle grass Species 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 10
- 244000230342 green foxtail Species 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 70
- 239000000460 chlorine Substances 0.000 description 70
- 229910052801 chlorine Inorganic materials 0.000 description 70
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 66
- 239000011737 fluorine Substances 0.000 description 66
- 229910052731 fluorine Inorganic materials 0.000 description 66
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 39
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 38
- 229910052794 bromium Inorganic materials 0.000 description 38
- 241000196324 Embryophyta Species 0.000 description 30
- 239000000203 mixture Substances 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 239000002994 raw material Substances 0.000 description 15
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 14
- 150000001299 aldehydes Chemical class 0.000 description 13
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
- 235000019441 ethanol Nutrition 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 10
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 7
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 6
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical class CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 5
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 230000002363 herbicidal effect Effects 0.000 description 5
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical class CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000000967 suction filtration Methods 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 4
- OHMBHFSEKCCCBW-UHFFFAOYSA-N hexane-2,5-diol Chemical compound CC(O)CCC(C)O OHMBHFSEKCCCBW-UHFFFAOYSA-N 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 3
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 3
- 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
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 3
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- QYCSNMDOZNUZIT-UHFFFAOYSA-N benzhydrylidenehydrazine Chemical compound C=1C=CC=CC=1C(=NN)C1=CC=CC=C1 QYCSNMDOZNUZIT-UHFFFAOYSA-N 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000004009 herbicide Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 235000013311 vegetables Nutrition 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- NHNUFAASKXPOQA-UHFFFAOYSA-N (3-acetamido-2-hydroxyphenyl)arsonic acid Chemical compound C(C)(=O)NC=1C(=C(C=CC1)[As](O)(=O)O)O NHNUFAASKXPOQA-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- WIHIUTUAHOZVLE-UHFFFAOYSA-N 1,3-diethoxypropan-2-ol Chemical compound CCOCC(O)COCC WIHIUTUAHOZVLE-UHFFFAOYSA-N 0.000 description 2
- OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical group C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 description 2
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 2
- WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- NPDLYUOYAGBHFB-WDSKDSINSA-N Asn-Arg Chemical compound NC(=O)C[C@H](N)C(=O)N[C@H](C(O)=O)CCCN=C(N)N NPDLYUOYAGBHFB-WDSKDSINSA-N 0.000 description 2
- 235000005781 Avena Nutrition 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 235000021506 Ipomoea Nutrition 0.000 description 2
- 241000207783 Ipomoea Species 0.000 description 2
- 241000209510 Liliopsida Species 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- 241000209117 Panicum Species 0.000 description 2
- 235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 2
- 235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000207763 Solanum Species 0.000 description 2
- 235000002634 Solanum Nutrition 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 2
- 125000005879 dioxolanyl group Chemical group 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
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- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- PUIYMUZLKQOUOZ-UHFFFAOYSA-N isoproturon Chemical compound CC(C)C1=CC=C(NC(=O)N(C)C)C=C1 PUIYMUZLKQOUOZ-UHFFFAOYSA-N 0.000 description 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- JVJQPDTXIALXOG-UHFFFAOYSA-N nitryl fluoride Chemical compound [O-][N+](F)=O JVJQPDTXIALXOG-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 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 2
- 239000000376 reactant Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 2
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 2
- 238000009333 weeding Methods 0.000 description 2
- HXOOTKIBIPSPNV-UHFFFAOYSA-N (4-chloro-2-methylphenyl) ethaneperoxoate Chemical compound CC(=O)OOC1=CC=C(Cl)C=C1C HXOOTKIBIPSPNV-UHFFFAOYSA-N 0.000 description 1
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 description 1
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 description 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
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- 229940031815 mycocide Drugs 0.000 description 1
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- 229920005615 natural polymer Polymers 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
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- 150000002825 nitriles Chemical class 0.000 description 1
- XITQUSLLOSKDTB-UHFFFAOYSA-N nitrofen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C=C1Cl XITQUSLLOSKDTB-UHFFFAOYSA-N 0.000 description 1
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- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
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- 238000001953 recrystallisation Methods 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
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- 229910052624 sepiolite Inorganic materials 0.000 description 1
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- 239000000377 silicon dioxide Substances 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
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- 238000005507 spraying Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 230000002195 synergetic effect Effects 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
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
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- 239000002699 waste material Substances 0.000 description 1
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- 150000003751 zinc Chemical class 0.000 description 1
Classifications
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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
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D521/00—Heterocyclic compounds containing unspecified hetero rings
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- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
- A01N47/44—Guanidine; Derivatives thereof
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- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
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- General Health & Medical Sciences (AREA)
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- Plural Heterocyclic Compounds (AREA)
Abstract
一类新的取代磺酰基脒基腙及其制备方法,其通
式如下:这类取代磺酰基脒基腙作为除草剂的活性化
合物具有高效的杀灭莠草的作用。
Description
本发明涉及新的取代磺酰基脒基腙、其制备方法以及作为除草剂之用途。
一些有除草性能的取代氨基胍基吖嗪已经公开过,例如N′-(4,6-二甲嘧啶-2-基)-N″-乙酰基氨基-N′″-(2-氯苯磺酰基)胍(参见EP-A121,082)。但氨基胍基吖嗪的除草作用至今常常仍不是完全满意的。
现发现了新的取代磺酰基脒基腙,其通式如下:
式中
R1代表可以被取代的芳基、芳烷基或杂芳基;
R2代表氢,或代表可被取代的烷基、芳基或芳烷基;
R3代表氢,或代表可被取代的烷基、链烯基、链二烯基、。炔烃基、(杂)芳基、芳烷基、芳烯基、烷氧基、烷氧羰基或二烷氨基,或与R2一起代表可被取代的链烷二基;
R4代表氢、囟素、羟基、烷基、囟代烷基、烷氧烷基、烷氧基、囟代烷氧基、烷硫基、囟代烷硫基、氨基、烷基氨基或二烷基氨基;
X代表氮或-CH基;
Y代表氮或-CR5基(R5代表氢、囟素、氰基、烷基、甲酰基、烷基羰基或烷氧基羰基;
Z代表氮或-CR6基(R6代表氢、囟素、羟基、烷基、囟代烷基、烷氧基、囟代烷氧基、烷硫基、烷氨基或二烷基氨基。
通式(Ⅰ)代表式(ⅠA)、(ⅠB)和(ⅠC)的任一种互变异构体,它们可能是
和这些互变异构体的混合物,也可能是在每一情况中由于C=N键而生成的E-异构体和Z-异构体和它们的混合物。
通式(Ⅰ)的新的取代磺酰基脒基腙的制取方法有:
(a)将通式(Ⅱ)的氨基胍
R1、R4、X、Y和Z的定义如上)与通式(Ⅲ)的羰基化合物反应
(式中
R2和R3的定义如上)或与N,N-二烷基羰酰胺缩醛或缩酮反应,适合时可在缩合助剂或稀释剂存在下进行;
(b)将通式(Ⅳ)的磺酰基化合物
(式中
R1、R4、X、Y和Z的定义如上
A代表囟素或一个如下的离去基团
(式中
R1的定义如上;
R7代表烷基、链烯基或芳烷基;
R8代表可被取代的烷基、芳烷基或芳基;
Q代表氧或硫))与通式(Ⅴ)的腙反应,
(式中
R2和R3的定义如上)适合时在稀释剂存在下进行。
新的通式(Ⅰ)的取代磺酰基脒基腙的特点是具有强力的除草活性。
通式(Ⅰ)的新化合物比结构类似和作用方式相同的已知化合物如N′-(4,6-二甲嘧啶-2-基)-N-乙酰氨基-N-(2-氯苯磺酰基)胍(参见EP-A 121,082)具有非常显著的更强力的除草作用。
本发明首先涉及这样的式(Ⅰ)化合物:其中
R9和R10是相同或不相同的,并代表氢、氟、氯、溴、碘、氰基、硝基、C1-C4烷基(可被氟、氯、溴、氰基、羧基、C1-C4烷氧羰基、C1-C4烷氨基羰基、二(C1-C4烷基)氨基羰基、羟基、C1-C4烷氧基、甲酰氧基C1-C4烷基羰氧基、C1-C4烷氨基羰氧基、C1-C4烷硫基、C1-C4烷亚硫酰基、C1-C4烷磺酰基、二(C1-C4)烷氨磺酰基、C3-C6环烷基或苯基所取代),或代表C-C链烯基(可被氟、氯、溴、氰基、C-C烷氧羰基、羧基或苯基所取代),或代表C2-C6炔基(可被氟、氯、溴、氰基、C1-C4烷氧基羰基、羧基或苯基所取代),或代表C1-C4烷氧基(可被氟、氯、溴、氰基、羧基、C1-C4烷氧羰基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷亚硫酰基或C1-C4烷磺酰基所取代),或代表C1-C4烷硫基(可被氟、氯、溴、氰基、羧基、C1-C4烷氧羰基、C1-C4烷硫基、C1-C4烷亚硫酰基或C1-C4烷磺酰基所取代),或代表C3-C6链烯氧基(可被氟、氯、溴、氰基或C1-C4烷氧羰基所取代),或代表C2-C6链烯硫基(可被氟、氯、溴、氰基、硝基、C1-C3烷硫基或C1-C4烷氧羰基所取代)、C3-C6炔氧基或C3-C6炔硫基,或代表-S(O))p-R11基团,其中
p代表1或2;
R11代表C1-C4烷基(可被氟、氯、溴、氰基或C1-C4烷氧基羰基所取代)、C3-C6链烯基、C3-C6炔基、苯基、C1-C4烷氧基、C1-C4烷氧C1-C4烷氨基、C1-C4烷氨基或二(C1-C4烷基)氨基,或代表-NHOR12,其中
R12代表C1-C12烷基(可被氟、氯、氰基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷亚硫酰基、C1-C4烷磺酰基、C1-C4烷基羰基、C1-C4烷氧基羰基、C1-C4烷氨基羰基或二(C1-C4烷基)氨基羰基,或代表C3-C6链烯基(可被氟、氯或溴所取代)、C3-C6炔基、C3-C6环烷基、C3-C6环烷基C1-C2烷基、苯基C1-C2烷基(可被氟、氯、硝基、氰基、C1-C4烷基、C1-C4烷氧基或C1-C4烷氧基羰基所取代),或代表二苯甲基,或代表苯基(可被氟、氯、硝基、氰基、C1-C4烷基、三氟甲基、C1-C4烷氧基、C1-C4氟代烷氧基、C1-C4烷硫基、三氟甲硫基或C1-C4烷氧基羰基所取代,
R9和R10还代表苯基或苯氧基,或代表氨基、C1-C4烷羰基氨基、C1-C4烷氨基羰基氨基或二(C1-C4烷基)氨基羰基氨基,或代表-CO-R13基团,其中
R13代表C1-C6烷基、C1-C6烷氧基(可被氟、氯、甲氧基或乙氧基所取代),或代表C3-C6环烷氧基、C3-C6链烯氧基、C1-C4烷硫基、C1-C4烷氨基、C1-C4烷氧氨基、C1-C4烷氧基C1-C4烷基氨基或二(C1-C4烷基)氨基(这些基团都可被氟和/或氯所取代);
R9和R10还可代表C1-C4烷磺酰氧基、二(C1-C4烷基)氨基磺酰基氨基或噻唑氧基,或代表-CH=N-R14基团,其中
R14代表C1-C6烷基(可被氟、氯、氰基、羧基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷亚硫酰基或C1-C4烷磺酰基所取代),或代表苄基(可被氟或氯所取代),或代表C3-C6链烯基或C3-C6炔基(都可被氟或氯所取代),或代表苯基(可被氟、氯、溴、C1-C4烷基、C1-C4烷氧基、三氟甲基、三氟甲氧基或三氟甲硫基所取代),或代表C1-C6烷氧基、C3-C6链烯氧基、C3-C6炔氧基或苄氧基(都可被氟和/或氯所取代),或代表氨基、苯基氨基C1-C4烷基羰基氨基、C1-C4烷氧基羰基氨基或C1-C4烷磺酰基氨基,或代表苯磺酰基氨基(可被氟、氯、溴或甲基所取代);
在式(Ⅰ)中还可以是
R1代表
其中
R15代表氢或C1-C4烷基;
R16和R17是相同或不相同的,并代表氢氢、氟、氯、溴、硝基、氰基、C1-C4烷基(可被氟和/或氯所取代),C1-C4烷氧基(可被氟和/或氯所取代、羧基、C1-C4烷氧羰基、C1-C4烷磺酰基或二(C1-C4烷基)氨基磺酰基;
在式(Ⅰ)中还可以是
R1代表
其中
R18和R19是相同或不相同的,并代表氢、氟、氯、溴、硝基、氰基、二甲氨基、C1-C4烷基(可被氟和/或氯所取代)或C1-C4烷氧基(可被氟和/或氯所取代);
在式(Ⅰ)中还可以是
R1代表
其中
R20和R21是相同或不相同的,并代表氢、氟、氯、溴、硝基、氰基、C1-C4烷基(可被氟和/或氯所取代)、C2-C4链烯基(可被氟和/或氯所取代)、C1-C4烷氧基(可被氟和/氯所取代),或代表C1-C4烷硫基、。C1-C4烷亚硫酰基或C1-C4烷磺酰基(都可被氟和/或氯所取代),也代表二(C1-C4烷基)氨磺酰基、C1-C4烷氧基羰基、二甲基氨羰基或二氧戊环;
在式(Ⅰ)中还可以是
R1代表
其中
R22和R23是相同或不相同的,并代表氢、氟、氯、溴、C1-C4烷基(可被氟和/或溴所取代)、C1-C4烷氧基(可被氟和/或氯所取代),或者代表C1-C4烷硫基、C1-C4烷亚磺酰基或C1-C4烷磺酰基(均可被氟和/或氯所取代),或代表二(C1-C4烷基)氨磺酰基;
在式(Ⅰ)中还可以是
R1代表
R24和R25是相同或不相同的,并代表氢、氟、氯、溴、氰基、硝基、C1-C4烷基(可被氟、氯、C1-C4烷氧基和/或C1-C4囟代烷氧基所取代)、C1-C4烷氧基(可被氟和/或氯所取代),或C1-C4烷硫基、C1-C4烷亚硫酰基或C1-C4烷磺酰基(均可被氟和/或氯所取代),二(C1-C4烷基)氨磺酰基、C1-C4烷氧羰基、二氧戊环基或2-噻唑基;
A代表氧、硫或N-Z1基
其中
Z1代表氢、C1-C4烷基(可被氟、氯、溴或氰基所取代)、C3-C6环烷基、苄基、苯基(可被氟、氯、溴或硝基取代)、C-C烷羰基、C1-C4烷氧基羰基或二(C1-C4烷基)氨基羰基;
在式(Ⅰ)中还可以是
R1代表
其中
R26代表氢、C1-C5烷基或囟素;
R27代表氢或C1-C5烷基;
Y1代表氧、硫或N-R28基(R28代表氢或C1-C5烷基);
在式(Ⅰ)中还可以是
R1代表基团
其中
R29代表氢、C1-C4烷基、苯基或(异)喹啉基;
R30代表氢、囟素、硝基、氰基、C1-C4烷基(可被氟和/或氯取代)、C1-C4烷氧基(可被氟和/或氯取代)、二氧戊环基或C1-C4烷氧基羰基;
R31代表氢、囟素或C1-C4烷基;
在式(Ⅰ)中还可以是
R1代表基团
其中
R32代表C1-C3烷基;
R33代表C1-C4烷基;
在式(Ⅰ)中还可以是
R1代表
,基团
其中
R34代表氢或甲基;
在式(Ⅰ)中还可以是
R1代表
其中
R35代表氢-囟素或C1-C4烷基;
R36代表氢、囟素、C1-C4烷基、C1-C4囟代烷基、C1-C4烷氧基或C1-C4囟代烷氧基;
Y代表氧或硫;
在式(Ⅰ)中还可以是
R1代表五甲基苯基;
R2代表氢,或代表C1-C6烷基(可被氟、氯和/或溴取代),或代表苯基或苄基(均可被氟、氯、溴、C1-C4烷基和/或C1-C4烷氧基取代);
R3代表氢、或代表C1-C20烷基、C2-C10链烯基、C2-C10炔基或C4-C10链二烯基(均可被氟、氯和/或溴取代),或代表C1-C4烷氧基C1-C4烷基,或代表苯基(可被氟、氯、溴、羧基、氰基、硝基、氨基、C1-C4烷基(可被氟和/或氯取代)、C1-C4烷氧基(可被氟和/或氯取代)、C1-C4烷硫基(可被氟和/或氯取代)、二(C1-C4烷基)氨基、C1-C4烷氧基羰基和/或苯氧基(可被氟、氯和/或三氟甲基取代),或代表萘基,或代表吡啶基、吡咯基、呋喃基、噻唑或噻吩基(均可被氰基、硝基、氟、氯、溴、C1-C4烷基和/或C1-C4烷氧基取代),或代表二噻吩基,或代表苯基C1-C2烷基或苯基乙烯基(均可被氟、氯、溴、C1-C4烷基和/或C1-C4烷氧基取代),或代表C1-C6烷氧基、C1-C6烷氧基羰基或二(C1-C4烷基)氨基,或与R2一起代表C2-C6链烷二基(可被氟、氯、溴、C1-C4烷基和/或C1-C4烷氧基羰基取代);
R4代表氢、氟、氯、溴、C1-C4烷基、C1-C4囟代烷基、C1-C2烷氧烷C1-C2烷基、二(C1-C2烷氧基)C1-C2烷基、C1-C4烷氧基、C1-C4囟代烷氧基、C1-C4烷硫基、C1-C4囟代烷硫基、氨基、C1-C4烷氨基、二甲氨基或二乙氨基;
X代表氮或-CH基;
Y代表氮或-CR5基(R5代表氢、氟、氯、溴、氰基、甲基、甲酰基、乙酰基、甲氧基羰基或乙氧基羰基;
Z代表氮或-CR6基(R6代表氢、氟、氯、溴、C1-C4烷基、三氟甲基、C1-C4烷氧基、二氟甲氧基、C1-C4烷硫基、C1-C4烷氨基、二甲基氨基或二乙基氨基)
本发明特别涉及
R1代表 基团的式(Ⅰ)化合物
式中
R9代表氟、氯、溴、氰基、甲基、三氟甲基、甲氧基、乙氧基、二氟甲氧基、三氟甲氧基C1-C3烷硫基、C1-C3烷亚磺酰基、C1-C3烷磺酰基,苯磺酰基、二甲基氨磺酰基、二乙基氨磺酰基、N-甲氧基-N-甲基氨磺酰基、苯基、苯氧基或C1-C3烷氧基羰基;
R10代表氢、氟、氯、溴、甲基或甲氧基;
在式(Ⅰ)中还可以是
其中
R15代表氢;
R16代表氟、氯、溴、氰基、甲基、甲氧基、乙氧基、二氟甲氧基、三氟甲氧基、甲氧基羰基、乙氧基羰基、甲磺酰基或二甲基氨磺酰基;
R17代表氢或氯;
在式(Ⅰ)中还可以是
R1代表 的基团(式中R代表C1-C2烷基),或
R1代表萘基
在式(Ⅰ)中还可以是
R2代表氢、C1-C4烷基或苯基;
R3代表C1-C4烷基;C2-C10链烯基或C4-C10链二烯基,或者代表苯基(可被氟、氯、溴、羧基、氰基、硝基、甲基、乙基、三氟甲基、甲氧基、乙氧基、二氟甲氧基、三氟甲氧基、甲硫基、乙硫基、二氟甲硫基、三氟甲硫基、二甲基氨基和/或苯氧基(可被氟、氯和/或三氟甲基取代)取代),或代表吡啶基、呋喃基、噻唑基或噻吩基(均可被氰基、硝基、氟、氯、溴、甲基、乙基、甲氧基或乙氧基取代),或代表二噻吩基,或代表苄基或苯乙烯基),或代表C1-C4烷氧基,C1-C4烷氧羰基或二甲基氨基,或与R2一起代表丁烷-1,4-二基(四亚甲基)或戊烷-1,5-二基(五亚甲基);
R4代表氢、氟、氯、溴、甲基、甲氧甲基、三氟甲基、甲氧基、乙氧基、二氟甲氧基、甲硫基、乙硫基、氨基、甲氨基、乙氨基、二甲氨基或二乙氨基;
X代表氮或-CH基;
Y代表氮或-CR5基(R5代表氢、氟、氯或甲基);
Z代表氮或-CR6基(R6代表氢、氟、氯和溴、甲基、乙基、三氟甲基、甲氧基、乙氧基、丙氧基、异丙氧基、二氟甲氧基、甲硫基、乙硫基、甲基氨基、乙基氨基、二甲基氨基或二乙基氨基。
如果原料使用N′-(4,6-二甲氧基嘧啶-2-基)N″-氨基-N′″-(2,6-二氟苯磺酰基)胍和丙酮,本发明(a)法的反应过程可概括如下面的反应方程:
如果原料使用N′-(4-甲氧基-6-甲基-S-三嗪-2-基)-N″-(2-三氟甲基苯磺酰基)-0-甲基异脲和苯乙酮腙,本发明的(b)法的过程可概括如下面的反应方程:
本发明制备式(Ⅰ)化合物的(a)法中,式(Ⅱ)给用作原料的氨基胍提供了一总的定义。
在式(Ⅱ)中,优先选择的R1、R4、X、Y和Z的定义是本发明在上面已经述及的关于式(Ⅰ)化合物的本发明优先选择或特别优先选择的R1、R4、X、Y和Z。
现将式(Ⅱ)的原料之例列于表1。
式(Ⅱ)的某些原料为已知物(参见EP-A 224,078,US P 4,725,303),而某些(作为除草剂)是较早的非在先公开的申请人公司的DE专利申请(P 3,818,040.5,88年5月27日)的主题。
通式(Ⅱ)化合物可按如下方法制备,使通式(Ⅳ)所示的磺酰基化合物与肼或与肼/水或肼/酸加合物反应,如果需要,有酸受体(如碳酸钾)存在,并且如果需要,在一种稀释剂(如甲醇,乙醇和/或水)存在下,在-20℃至+100℃温度下反应,
式中,R1,R4,X,Y和Z定义同上,
A表示囟素或下述离去基团之一,
其中R1定义同上,
R7表示烷基,链烯基或芳烷基,
R8在各种情况下代表可任选取代的烷基,芳烷基或芳基,
Q代表氧或硫,
某些式(Ⅱ)化合物也可按下面概述的方法制得(R是上述R情况下所指出的那些基团)
(至于反应原理,见US P 4,659,364和EP-A 173319)。
式(Ⅳ)规定了作为中间体所需要的磺酰基化合物的总的定义。式(Ⅳ)中,R1,R4,X,Y和Z较好,或特别好的定义是说明书中对本发明化合物(Ⅰ)所给出的R1,R4,X,Y和Z上面那些较好或特别好的定义,
A最好表示氯或下述离去基团之一,
式中R1具有上述优选的定义,
R7表示C1-C4烷基,C3-C4链烯基或苄基,
R8表示任选地被羧基、C1-C4-烷氧基羰基或C1-C4烷氧基取代的C1-C4烷基,或表示苄基或苯基,它们又都可任选地被氟、氯、溴、C1-C4烷基或C1-C4烷氧基取代,以及
Q表示氧或硫。
式(Ⅳ)化合物的实例列于下面表2中。
式(Ⅳ)所示化合物为已知物并且/或者可用实质上已知的方法来制备(参见EP-A 5,986,EP-A 24,215,EP-A 121,082,EP-A 172,975,EP-A 173,321,EP-A-173,956,EP-A 224,078,DE-OS(德国公开说明书)3,634,928和DE-OS(德国公开说明书)3,634,929)。
式(Ⅲ)规定了在本发明方法(a)中用以制备式(Ⅰ)化合物的原料的另一种羰基化合物的总的定义。
在式(Ⅲ)中,R2和R3的定义较好是,或特别是,在叙述本发明式(Ⅰ)化合物时上面已经提到的R2和R3的那些较好的,或特别好的定义。
作为式(Ⅲ)原料的实例,可以提及下述基团:甲醛,乙醛,丙醛,丁醛,异丁醛,戊醛,异戊醛,苯甲醛,吡啶-4-,-2-和-3-甲醛,呋喃-2-和-3-甲醛和噻吩-2-和-3-甲醛,还有丙酮,甲基乙基酮,甲基丙基酮,甲基异丙基酮,甲基丁基酮,甲基异丁基酮,二乙基酮,乙酰苯,二苯酮,环戊酮,环己酮,苯基丙酮,氯丙酮,三氯乙醛,乙醛酸甲酯,乙醛酸乙酯,丙酮酸甲酯和丙酮酸乙酯,苯醛酸和6-氯吡啶-3-醛。
还可以用作本发明方法(a)的原料的N,N-二烷基羧酰胺缩醛或缩酮类最好是在N或O上连有1-4个碳原子的直链或支链烷基的N,N-二烷基甲酰胺缩醛类或缩酮类或者N,N-二烷基乙酰胺缩醛类或缩酮类,例如,N,N-二甲基甲酰胺醛缩二甲醇,N,N-二甲乙酰胺醛缩二甲醇,N,N-二乙基甲酰胺醛缩二甲醇,N,N-二乙基乙酰胺醛缩二甲醇,N,N-二甲基甲酰胺醛缩二乙醇,N,N-二甲基乙酰胺醛缩二乙醇,N,N-二乙基甲酰胺醛缩二乙醇,N,N-二乙基乙酰胺醛缩二乙醇,N,N-二甲基甲酰胺醛缩二丙醇,N,N-二甲基乙酰胺醛缩二丙醇,N,N-二乙基甲酰胺醛缩二丙醇,N,N-二乙基乙酰胺醛缩二丙醇,N,N-二甲基甲酰胺醛缩二异丙醇,N,N-二甲基乙酰胺醛缩二异丙醇,N,N-二乙基甲酰胺醛缩二异丙醇,N,N-二乙基乙酰胺醛缩二异丙醇,N,N-二甲基甲酰胺醛缩二丁醇,N,N-二甲基乙酰胺醛缩二丁醇,N,N-二乙基甲酰胺醛缩二丁醇,N,N-二乙基乙酰胺醛缩二丁醇,N,N-二甲基甲酰胺醛缩二异丁醇,N,N-二甲基乙酰胺醛缩二异丁醇,N,N-二乙基甲酰胺醛缩二异丁醇,N,N-二乙基乙酰胺醛缩二异丁醇,N,N-二甲基甲酰胺醛缩二仲丁醇,N,N-二甲基乙酰胺醛缩二仲丁醇,N,N-二乙基甲酰胺醛缩二仲丁醇,N,N-二乙基乙酰胺醛缩二仲丁醇,N,N-二甲基甲酰胺醛缩二叔丁醇,N,N-二甲基乙酰胺醛缩二叔丁醇,N,N-二乙基甲酰胺醛缩二叔丁醇和N,N-二乙基乙酰胺醛缩二叔丁醇。
式(Ⅲ)所示的原料是有机合成中的已知化学品。
如果需要,实行制备式(Ⅰ)新化合物的本发明方法(a)时使用稀释剂。用于此目的的合适稀释剂实际上是所有的惰性有机溶剂。较好的溶剂包括脂肪族和芳香族、也可以是卤代的烃类,如戊烷,己烷,庚烷,环己烷,石油醚,汽油,ligroin,苯,甲苯,二甲苯,二氯甲烷,二氯乙烷,氯仿,四氯化碳,氯苯和邻二氯苯,醚类,如乙醚,二丁醚,乙二醇二甲醚,二乙二醇二甲醚,四氢呋喃和二噁烷,醇类,如甲醇,乙醇,丙醇,异丙醇,丁醇和异丁醇,酯类,如乙酸甲酯和乙酸乙酯,腈类,如乙腈和丙腈,酰胺类,如二甲基甲酰胺,二甲基乙酰胺和N-甲基吡咯烷酮,还有二甲亚砜,环丁砜和六甲基磷酰胺。
如果需要,在缩合助剂存的下实行本发明方法(a)。合适的缩合助剂较好的是有机化学中惯用的干燥剂。其中较好的包括无水盐类,如硫酸钠,硫酸镁和碳酸钾。
在执行本发明方法(a)时,反应温度可在大范围内变化,通常,本方法在0℃-100℃、较好是10℃-80℃温度范围内进行。
本发明方法(a)通常在大气压下进行。然而,也可以在增压或减压条件下进行。
为了实行本发明方法(a),相对于每摩尔的式(Ⅱ)所示的氨基胍,通常使用1-1000摩尔、较好是1-500摩尔的式(Ⅲ)所示的羰基化合物。
通常,在室温或稍冷条件下将反应物混合,如果需要,在升温条件下搅拌,直至反应完成。通过惯用方法进行处理(参见制备实施例)。
式(Ⅳ)规定了在本发明方法(b)中制备式(Ⅰ)化合物时用作原料的磺酰基化合物的总的定义。该磺酰基化合物中较好和特别好的一组化合物已在上面给予定义。式(Ⅳ)所示原料的实例列在面表2中。
式(Ⅴ)规定了在本发明方法(b)中制备式(Ⅰ)所示化合物时也用作原料的腙类的总的定义。
式(Ⅴ)中,R2和R3较好的或特别好的定义是在上述叙述本发明式(Ⅰ)化合物时提及的R2和R3较好的或特别好的那些定义。
下面提到的化合物是式(Ⅴ)所示原料的实例:
乙醛腙,丙醛腙,丁醛腙,异丁醛腙,戊醛腙,异戊醛腙,苯甲醛腙,吡啶-2-,-3-和-4-醛腙,呋喃-2-和-3-醛腙,噻吩-2-和-3-醛腙,丙酮腙,甲基乙基酮腙,甲基丙基酮腙,甲基异丙基酮腙,甲基丁基酮腙,甲基异丁基酮腙二乙基酮腙,乙酰苯腙,二苯酮腙,环戊酮腙和环己酮腙。
式(Ⅴ)所示原料为已知有机化学品。
制备式(Ⅰ)新化合物的本发明方法(b)最好采用稀释剂进行。此处适用的稀释剂是与上面对本发明方法(a)所指出的稀释剂相同的有机溶剂。
执行本发明方法(b)时,反应温度可以在大范围内变化。通常,该方法在0℃-150℃、较好是20℃-120℃温度范围内进行。
本发明方法(b)通常在大气压下进行。但是也可以在增压或减压条件下进行。
为了进行本发明方法(b)的反应,相对于每摩尔的式(Ⅳ)所示磺酰基化合物,式(Ⅴ)所示腙的用量通常是1-10摩尔、较好是1-5摩尔。
通常,反应物在室温下混合,并且,如果需要,在升温条件下搅拌混合物,直至反应完全。用常用方法进行处理(参见制备实施例)。
本发明活性化合物可用作脱叶剂,脱水剂,破坏阔叶植物的药剂,以及,特别是用作除草剂。广义地说,应将杂草理解为人们不希望其在某处生长的所有植物。本发明物质作为全部除草还是作为选择性除草的除草剂,这基本上取决于所用的量。
本发明的活性化合物例如可用于下述植物:
以下各属的双子叶植物:芥子属,独行菜属,猪殃殃属,繁缕属,母菊属,春黄菊属,牛膝菊属,藜属,荨麻属,千里光属,苋属,马齿苋属,苍耳属,旋花属,番薯属,蓼属,田菁属,豚草属,蓟属,飞廉属,苦苣菜属,茄属,蔊菜属,水松草属,母草属,野芝麻属,婆婆纳属,苘麻属,Emex,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。
以下各属的双子叶栽培植物:棉属,大豆属,甜菜属,胡萝卜属,菜豆属,豌豆属,茄属,亚麻属,番薯属,巢菜属,烟草属,番茄属,花生属,芸苔属,莴苣属,黄瓜属和南瓜属。
以下各属的单子叶杂草:稗属,狗毛草属,黍属,马唐属,梯牧草属,早熟禾属,羊茅属,蟋蟀草属,Branchiaria,毒麦属,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,慈姑属,荸荠属,藨草属,雀稗属,Ischaemum,尖瓣花属,龙爪茅属,翦股颖属,看麦娘属和Apera。
以下各属的单子叶培养植物: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。
但是本发明活性化合物的应用决不限于这些种属,还可以同样方式扩展到其它植物。
该化合物适用于(根据所用浓度)杀灭全部杂草,例如对工业区和铁路线上,以及道路和广场上,不论是否有种植的树木,都可用来杀灭全部杂草。同样,该化合物可用于杀灭多年生栽培植物中的杂草,例如所述植物有人造林,装饰性植物,果园,葡萄园,柑桔林,坚果园,香蕉种植区,咖啡种植园,茶树种植园,橡胶种植园,软果种植和蛇麻草田,在草场,草皮和牧场,以及在一年生栽培植物中选择性杀灭杂草。
本发明的式(Ⅰ)化合物特别适用于通过芽前及芽后方法杀灭单子叶作物中的双子叶杂草。
该活性化合物可以制成常用制剂,如溶液,乳液,可湿性粉剂,悬浮液,粉剂,喷粉剂,糊剂,可溶性粉剂,粒剂,悬浮-乳油,用活性化合物浸渍的天然和合成材料以及用聚合物质做成的很细小的胶囊。
这些制剂是用已知方法制成的,这些方法例如是将活性化合物与扩展剂混合;这些扩展剂是液体溶剂和/或固体载体;也可以使用表面活性剂,即乳化剂和/或分散剂以及/或者发泡剂。
在用水作扩展剂的情况下,也可以使用例如有机溶剂作为助溶剂。合适的液体溶剂主要有:芳香化合物,如二甲苯,甲苯,或烷基萘,氯代芳香化合物和氯代脂肪烃,如氯苯,氯乙烯或二氯甲烷,脂肪烃,如环己烷或石蜡油,如石油馏分,矿物油或植物油,醇类,如丁醇或乙二醇以及它们的醚和酯类,酮类,如丙酮,甲基乙基酮,甲基异丁基酮,或环己酮,强极性溶剂,如二甲基甲酰胺和二甲基亚砜,以及水。
合适的固体载体有:如铵盐和磨细的天然材料,如高岭土,粘土,滑石,白垩,石英,硅镁土,蒙脱土或硅藻土,以及磨细的合成材料,如高度分散的硅石,氧化铝以及硅酸盐,颗粒剂的合适固体载体有:例如压碎并分级的天然材料,如方解石,大理石,浮石,海泡石,白云石,以及无机和有机粗粉合成颗粒,和有机材料颗粒,如锯末,椰子壳,玉米棒子和烟草茎;合适的乳化剂和/或发泡剂有: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,如烷基芳基聚乙二醇醚,烷基磺酸盐,烷基硫酸盐类,芳基磺酸盐类,以及白蛋白水解产物;适合的分散剂有:例如木素亚硫酸盐废液和甲基纤维素。
粘附剂如羧甲基纤维素和粉状、粒状或胶乳状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,和合成的磷脂可用在制剂中。另外的添加剂可以是矿物油和植物油。
有可能使用着色剂,如无机颜料,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,和少量的营养物,如铁盐,锰盐,硼盐,铜盐,钴盐,钼盐和锌盐。
制剂中通常含有0.1-95%重量的活性化合物,较好是0.5-90%。
用于除去杂草时,本发明活性化合物可以本身或以其制剂形式与其它已知除草剂、成品制剂制成混合物或可能的桶混物使用。
制成混合物的合适除草剂有以下已知除草剂,如1-氨基-6-乙硫基-3-(2,2-二甲基丙基)-1,3,5-三嗪-2,4-(1H,3H)-二酮(AMETHYDIONE),或N-(2-苯并噻唑基)-N,N′-二甲基脲(METABENZTHIAZURON),用于除去谷物中的杂草;4-氨基-3-甲基-6-苯基-1,2,4-三嗪-5(4H)-酮(甲苯嗪),用于除去糖甜菜中的杂草,以及4-氨基-6-(1,1-二甲基乙基)-3-甲硫基-1,2,4-三嗪-5(4H)-酮(噻克嗪),用于除去大豆中的杂草;还有2,4-二氯苯氧乙酸(2,4-D);4-(2,4-二氯苯氧基)丁酸(2,4-DB);2,4-二氯苯氧基丙酸(2,4-DP);3-异丙基-2,1,3-苯并噻二嗪-4-酮2,2-二氧化物(苯达松);5-(2,4-二氯苯氧基)-2-硝基苯甲酸甲酯(甲酯除草醚);3,5-二溴-4-羟基苯甲腈(溴草腈);2-氯-N-{〔(4-甲氧基-6-甲基-1,3,5-三嗪-2-基)氨基〕羰基}苯磺酰胺(CHLORSULFURON);N,N-二甲基-N′-(3-氯-4-甲基苯基)脲(绿麦隆);2-〔4-(2,4-二氯苯氧基)苯氧基〕丙酸及其甲基酯或乙基酯(2,4-滴苯丙酸);2-{4-〔(6-氯-2-苯并唑基)氧〕苯氧基}丙酸及其甲酯或乙酯(FENOXAPROP);〔(4-氨基-3,5-二氯-6-氟-2-吡啶基)氧〕乙酸或其1-甲基庚酯(FLUROXYPYR);2-〔4,5-二氢-4-甲基-4-(1-甲基乙基)-5-氧代-1H-咪唑-2-基〕-4(5)甲基苯甲酸甲酯(IMAZAMETHABENZ);3,5-二碘-4-羟基苯甲腈(碘草腈);N,N-二甲基-N′-(4-异丙基苯基)脲(异丙隆);(2-甲基-4-氯苯氧基)乙酸(2甲4氯);(4-氯-2-甲基苯氧基)丙酸(2甲4氯丙酸);N-甲基-2-(1,3-苯并噻唑-2-基氧)乙酰苯胺(MEFENACET);2-{〔〔((4-甲氧基-6-甲基-1,3,5-三嗪-2-基)氨基〕羰基〕氨基〕磺酰基}苯甲酸或其甲酯(MESULFURON);N-(1-乙基丙基)-3,4-二甲基-2,6-二硝基苯胺(PENDIMETHALIN);0-(6-氯-3-苯基哒嗪-4-基)S-辛基硫代氨基甲酸酯(PYRIDATE);4-乙基氨基-2-叔丁基氨基-6-甲硫基-S-三嗪(特丁草净);3-〔〔〔〔4-甲氧基-6-甲基-1,3,5-三嗪-2-基〕氨基〕羰基〕氨基〕磺酰基〕噻吩-2-羧酸甲酯(THIAMETURON)和S-2,3,3-三氯烯丙基N,N-二异丙基硫代氨基甲酸酯(三氯烯丹)。令人惊奇的是,某些混合物还表现出协同效应。
也可以是与其它已知活性化合物的混合物,这些化合物例如是杀真菌剂,杀虫剂,杀螨剂,杀线虫剂,驱鸟剂,植物营养素和改善土壤结构的制剂。
该活性化合物在使用时可以是其自身、其制剂形式或通过进一步稀释由此制得其使用形式,如可直接使用的溶液,悬浮液,乳液,粉剂,糊剂和颗粒剂。其施用方式是常用的,如酒水,喷雾,雾化或撒播。
本发明的活性化合物在植物出土前或出土后都可以使用。
该化合物也可以在播种前掺入土壤中。
活性化合物的用量可以在很大范围内变化。这实质上取决于要达到什么性质的效果。通常该用量每公顷土壤表面为0.01-10千克活性化合物,最好是0.05-5千克/公顷。
从下面的实施例可以看出本发明活性化合物的制备和使用方法。
制备实施例:
实施例1
(方法(a))
将8.2克(0.02摩尔)N′-(4-甲氧基-6-甲基-嘧啶-2-基)-N″-氨基-N″′-(1-甲基-4-乙氧羰基-吡唑-5-基-磺酰基)-胍、5.6克(0.04摩尔)2-氯-苯甲醛和50毫升乙腈的混合物在20℃搅拌20小时。以结晶形式得到的产品通过抽滤分离出来。
得到7.5克(理论产率的70%)N′-(4-甲氧基-6-甲基-嘧啶-2-基)-N″-(2-氯-亚苄基氨基)-N″′-(1-甲基-4-乙氧羰基-吡唑-5-基-磺酰基)-胍,熔点185℃。
实施例2
(方法(a))
将8.2克(0.02摩尔)N′-(4-甲氧基-6-甲基-嘧啶-2-基)-N″-氨基-N″′-(1-甲基-4-乙氧羰基-吡唑-5-基-磺酰基)-胍,5.7克(0.04摩尔)2,6-二氟苯甲醛和50毫升乙醇的混合物在60℃搅拌20小时。在混合物冷至20℃以后,通过抽滤分离出以结晶形式得到的产品。
得到9.2克(理论量的86%)N′-(4-甲氧基-6-甲基-嘧啶-2-基)-N″-(2,6-二氟亚苄基氨基)-N″′-(1-甲基-4-乙氧羰基吡唑-5-基-磺酰基)-胍,熔点177℃。
实施例3
(方法(a))
将0.5克(1.2毫摩尔)N′-(4,6-二甲氧基-均三嗪-2-基)-N″-氨基-N″′-(2-甲氧羰基苯基磺酰基)-胍、20毫升丙酮、2克硫酸钠和10毫升二氯甲烷的混合物在20℃搅拌20小时,然后过滤。用50毫升二氯甲烷洗涤过滤残留物,蒸发母液,残留物中加乙醚研制,令其结晶,用抽滤法分离结晶产物。
得到0.34克(理论量的62%)N′-(4,6-二甲氧基-均-三嗪-2-基)-N″-(1-甲基亚乙基氨基)-N″′-(2-甲氧羰基-苯磺酰基)-胍,熔点175℃。
实施例4
(方法(a))
将1.8克(4.5毫摩尔)N′-(4-甲氧基-6-甲基-均-三嗪-2-基)-N″-氨基-N″′-(2-甲氧羰基-噻吩-3-基-磺酰基)-胍、0.71克(6.7毫摩尔)苯甲醛、2克硫酸钠和30毫升氯仿的混合物回流12小时,然后过滤。过滤残留物用50毫升氯仿洗涤。蒸发过滤得到的氯仿溶液,残留物与乙醚一起搅拌,用抽滤法分离以结晶形式得到的产品。
得到2.05克(理论量的94%)N′-(4-甲氧基-6-甲基-均-三嗪-2-基)-N″-亚苄基氨基-N″′-(2-甲氧羰基-噻吩-3-基-磺酰基)-胍,熔点215℃。
实施例5
(方法(a))
将4.2克(0.01摩尔)N′-(4-甲氧基-6-甲氧基甲基-嘧啶-2-基)-N″-氨基-N″′-(2-甲氧羰基-苯磺酰基)-胍和50毫升苯甲醛的混合物在20℃搅拌7天。用抽滤法分离出以结晶形式得到的产品。
得到2.0克(理论量的39%)N′-(4-甲氧基-6-甲氧甲基-嘧啶-2-基)-N″-亚苄基氨基-N″′-(2-甲氧羰基-苯磺酰基)-胍,熔点209℃。
实施例6
(方法(a))
将4.3克(0.01摩尔)N′-(4,6-二甲氧基-嘧啶-2-基)-N″-氨基-N″′-(2-苯基-苯磺酰基)-胍和2毫升二甲酰胺醛缩二甲醇的混合物在20℃搅拌60分钟;用抽滤法分离出以结晶形式得到的产品。
得到4.6克(理论量的95%)N′-(4,6-二甲氧基嘧啶-2-基)-N″-二甲基氨基亚甲基氨基-N″′-(2-苯基-苯磺酰基)-胍,熔点139℃。
实施例7
(方法(a))
将8.42克(0.02摩尔)N′-(4-甲氧基-6-甲基-均三嗪-2-基)-N″-氨基-N″′-(2-三氟甲氧基-苯磺酰基)胍、5毫升二甲基甲酰胺醛缩二叔丁醇和100毫升四氢呋喃的混合物在20℃搅拌15小时,然后用水慢慢稀释到大约两倍体积。通过抽滤分离出以结晶形式得到的本方法产物。
得到2.2克(理论量的22%)N′-(4-甲氧基-6-甲基-均三嗪-2-基)-N″-(叔丁氧基-亚甲基氨基)′N″′-(2-三氟甲氧基-苯磺酰基)-胍,熔点182℃。
实施例8
(方法(b))
将11.8克(0.02摩尔)N′-(4,6-二甲基嘧啶-2-(基)-N″-甲氧基-N″,N″′-双-(2-甲氧羰基-苯磺酰基)-胍、5.9克(0.03摩尔)二苯酮腙和100毫升二烷的混合物回流2天。待混合物冷却以后,滤除未反应的二苯酮腙,浓缩滤液,残留物用乙醇重结晶。
得到4.7克(理论量的43%)N′-(4,6-二甲基-嘧啶-2-基)-N″-二苯基亚甲基氨基-N″′-(2-甲氧羰基-苯磺酰基)-胍,熔153℃。
下面表3中列出的式(Ⅰ)化合物是可以通过与实施例1-8类似的方法并按照本发明制备方法的概括叙述而制得的其它实例化合物。
(表3中所用的缩写“decomp.”意思是“分解”)
式(Ⅱ)之原料:
实例(Ⅱ-1)
将1.3g(0.025mol)水合肼加入15.9g(0.025mol)N′-(4,6-二甲氧基-嘧啶-2-基)-N″-甲氧基-N″-(2-甲氧基羰基苯磺酰基)-N″′-(2-甲氧基羰基苄磺酰基)胍于100ml甲醇的悬浮液中,起始温度为20℃,同时搅拌,在反应过程中,反应混合物的温度升至30℃,形成清澈的溶液。在20-30℃下经4小时搅拌后沉淀出产品结晶,用吸滤法分离。得到N′-(4,6-二甲氧基嘧啶-2-基-N″-氨基-N″′-(2-甲氧基羰基苄磺酰基)胍9.5g(理论得率的89%),熔点166℃。
实例(Ⅱ-2)
于20℃下将1.0g(0.02mol)的水合肼搅拌加入8.3g(0.02mol)N′-4,6-二甲氧基-S-三嗪-2-基)-N″-(2-甲硫基苯磺酰基)-S-甲基异硫脲和80ml二氯甲烷的混合物中,混合物在20℃下搅拌30分钟。浓缩。残渣用乙醇研磨,得到的产品结晶用吸滤法分离。得到5.5g(理论得率的69%)N′-(4,6-二甲氧基-S-三嗪-2-基)N″-氨基-N″′-(2-甲硫基苯磺酰基)胍,熔点147℃。
可按类似于实例(Ⅱ-1)和(Ⅱ-2)的方法制备的式(Ⅱ)化合物的例子列于表4(decom.表示“分解”)
上述(Ⅱ-1)和(Ⅱ-2)的化合物以及表4所述(Ⅱ-3)至(Ⅱ-94)的化合物是新化合物,它们本身也有除草作用,这些化合物也是本发明的主题。
应用实例
在下面的各应用实例中,使用下述化合物作为对比化合物:
N′-(4,6-二甲基嘧啶-2-基)-N″-乙酰氨基-N'''-(-2-氯代苯磺酰基)胍(公开于EP-A 121,082)
现将应用实例中所用的本发明各化合物的化学式列于下。制备实例使用基编号(即实例号)。
实例A
芽前试验
溶剂:5重量份丙酮
乳化剂:1重量份烷芳基聚乙二醇醚
活性化合物的适合制剂按下法制备:1重量份活性化合物与上述量溶剂混合,加入上述量的乳化剂。将此浓液用水稀释至所需浓度。
将受试植物的种子播于通常的土壤中,24小时后,洒以活性化合物的制剂,每单位面积应保持常数量的水。活性化合物制剂中的浓度是不重要的,每单位面积所施的活性化合物的量才是决定性的。三周以后,植物受损害的程度以未处理的对照植物的生长作对比按%进行评定:
0%代表无作用(类似未处理的对照植物)
100%代表完全损害。
与先有技术对比,在此试验中显示了非常明显的高活性。例如下述制备实例中的化合物:3,67,68,80,83,85,87,88,92,93,95,99,101,108,116,117,258,269,270,271,272,273,275,276,278,284,285及286。
实例B
芽后试验
溶剂:5重量份丙酮
乳化剂:1重量份烷芳基聚乙二醇醚
按下述方法制备活性化合物的适合制剂:将1重量份的活性化合物与上述量溶剂混合,加入上述量的乳化剂。用水将此浓液稀释至所需浓度。
用活性化合物制剂喷洒5-15cm高的受试植物,使每单位面积有所需的特定活性化合物量。喷洒液的浓度的选择应使所需的特定活性化合物量为1000升水/公顷。三周后,植物受损害的程度以未处理的对照植物的生长作对比按%进行评定;
0%代表无作用(类似未处理的对照植物)
100%代表完全损害
与先有技术对比,在此试验中显示了非常高的活性。例如下述制备实例中的化合物:5,9,10,11,67,68,71,72,73,80,83,86,87,88,93,95,97,98,99,100,101,102,106,107,108,109,111,115,116,117,123,125,126,127,128,257,269,270,276,278,283,286,287和291。
Claims (6)
1、通式(Ⅰ)的取代磺酰基脒基腙
式中
R1代表可以被取代的芳基、芳烷基或杂芳基;
R2代表氢,或代表可被取代的烷基、芳基或芳烷基;
R3代表氢,或代表可被取代的烷基、链烯基、链二烯基、。炔烃基、(杂)芳基、芳烷基、芳烯基、烷氧基、烷氧羰基或二烷氨基,或与R2一起代表可被取代的链烷二基;
R4代表氢、卤素、羟基、烷基、卤代烷基、烷氧烷基、烷氧基、卤代烷氧基、烷硫基、卤代烷硫基、氨基、烷基氨基或二烷基氨基;
X代表氮或-CH基;
Y代表氮或-CR5基(R5代表氢、卤素、氰基、烷基、甲酰基、烷基羰基或烷氧基羰基;
Z代表氮或-CR5基(R5代表氢、卤素、羟基烷基、卤代烷基、烷氧基、卤代烷氧基、烷硫基、烷氨基或二烷基氨基。
2、权利要求1的通式(Ⅰ)的取代磺酰基脒基腙的制备方法,其特征在于
(a)将通式(Ⅱ)的氨基胍
(式中
R1、R4、X、Y和Z的定义如上)与通式(Ⅲ)的羰基化合物反应
(式中
R2和R3的定义如上)
或与N,N-二烷基羰酰胺缩醛或缩酮反应,适合时可在缩合助剂或稀释剂存在下进行;
(b)将通式(Ⅳ)的磺酰基化合物
(式中
R1、R4、X、Y和Z的定义如上
A代表卤素或一个如下的离去基团
或-Q-R8,
(式中
R1的定义如上;
R7代表烷基、链烯基或芳烷基;
R8代表可被取代的烷基、芳烷基或芳基;
Q代表氧或硫))
与通式(Ⅴ)的腙反应,
(式中
R2和R3的定义如上)
适合时在稀释剂存在下进行。
3、一类除草剂,其特征在于它含至少一种权利要求1的式(Ⅰ)取代磺酰基脒基腙。
4、一种除莠草的方法,其特征在于将权利要求1的式(Ⅰ)化合物施于莠草和/或其环境中。
5、使用权利要求1的式(Ⅰ)磺酰基脒基腙杀灭莠草。
6、除草剂的制备方法,其特征在于将权利要求1的式(Ⅰ)磺酰基脒基腙与扩展剂和/或表面活性剂相混合。
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3933792.8 | 1989-10-10 | ||
DE3933792 | 1989-10-10 | ||
DE4017460A DE4017460A1 (de) | 1989-10-10 | 1990-05-31 | Substituierte sulfonylamidinohydrazone |
DE4017460.3 | 1990-05-31 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN1050873A true CN1050873A (zh) | 1991-04-24 |
Family
ID=25885970
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN90107113A Pending CN1050873A (zh) | 1989-10-10 | 1990-10-10 | 取代的磺酰基脒基腙 |
Country Status (10)
Country | Link |
---|---|
US (1) | US5167692A (zh) |
EP (1) | EP0431270A1 (zh) |
JP (1) | JPH03133965A (zh) |
KR (1) | KR910007916A (zh) |
CN (1) | CN1050873A (zh) |
AU (1) | AU623554B2 (zh) |
BR (1) | BR9005031A (zh) |
CA (1) | CA2027042A1 (zh) |
DE (1) | DE4017460A1 (zh) |
HU (1) | HUT57743A (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101453895B (zh) * | 2006-05-22 | 2012-09-05 | 梅里亚有限公司 | 使用4-氨基-5-氯-噻吩并[2,3-d]-嘧啶化合物的杀虫方法 |
CN117304076A (zh) * | 2023-11-28 | 2023-12-29 | 苏州大学 | 一种n-磺酰基脒化合物的制备方法 |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2090045T3 (es) * | 1988-09-09 | 1996-10-16 | Ciba Geigy Ag | Plaguicidas. |
DE4110882A1 (de) * | 1991-04-04 | 1992-10-08 | Bayer Ag | Sulfonylguanidinoazine |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4750930A (en) * | 1983-01-04 | 1988-06-14 | E. I. Du Pont De Nemours And Company | Herbicidal N-hydroxy-N'-sulfonylguanidines |
DE3334455A1 (de) * | 1983-03-04 | 1984-09-06 | Bayer Ag, 5090 Leverkusen | Guanidin - derivate |
DE3602679A1 (de) * | 1986-01-30 | 1987-08-06 | Bayer Ag | Acylierte sulfonylguanidine |
-
1990
- 1990-05-31 DE DE4017460A patent/DE4017460A1/de not_active Withdrawn
- 1990-09-17 US US07/583,933 patent/US5167692A/en not_active Expired - Fee Related
- 1990-09-27 EP EP90118519A patent/EP0431270A1/de not_active Withdrawn
- 1990-10-05 CA CA002027042A patent/CA2027042A1/en not_active Abandoned
- 1990-10-09 JP JP2269657A patent/JPH03133965A/ja active Pending
- 1990-10-09 AU AU63954/90A patent/AU623554B2/en not_active Ceased
- 1990-10-09 HU HU906387A patent/HUT57743A/hu unknown
- 1990-10-09 BR BR909005031A patent/BR9005031A/pt not_active Application Discontinuation
- 1990-10-10 CN CN90107113A patent/CN1050873A/zh active Pending
- 1990-10-10 KR KR1019900016005A patent/KR910007916A/ko not_active Application Discontinuation
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101453895B (zh) * | 2006-05-22 | 2012-09-05 | 梅里亚有限公司 | 使用4-氨基-5-氯-噻吩并[2,3-d]-嘧啶化合物的杀虫方法 |
CN117304076A (zh) * | 2023-11-28 | 2023-12-29 | 苏州大学 | 一种n-磺酰基脒化合物的制备方法 |
CN117304076B (zh) * | 2023-11-28 | 2024-02-20 | 苏州大学 | 一种n-磺酰基脒化合物的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
BR9005031A (pt) | 1991-09-10 |
HU906387D0 (en) | 1991-04-29 |
EP0431270A1 (de) | 1991-06-12 |
AU623554B2 (en) | 1992-05-14 |
KR910007916A (ko) | 1991-05-30 |
DE4017460A1 (de) | 1991-04-18 |
HUT57743A (en) | 1991-12-30 |
US5167692A (en) | 1992-12-01 |
JPH03133965A (ja) | 1991-06-07 |
CA2027042A1 (en) | 1991-04-11 |
AU6395490A (en) | 1991-04-26 |
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