CN1082954C - 肟衍生物及其作为杀真菌剂的用途 - Google Patents
肟衍生物及其作为杀真菌剂的用途 Download PDFInfo
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- CN1082954C CN1082954C CN97198888A CN97198888A CN1082954C CN 1082954 C CN1082954 C CN 1082954C CN 97198888 A CN97198888 A CN 97198888A CN 97198888 A CN97198888 A CN 97198888A CN 1082954 C CN1082954 C CN 1082954C
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- methyl
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- 150000002923 oximes Chemical class 0.000 title claims abstract description 17
- 239000000417 fungicide Substances 0.000 title abstract 2
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 84
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 45
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 36
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 35
- 239000001301 oxygen Substances 0.000 claims abstract description 31
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 31
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 23
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 20
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 19
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 19
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 14
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
- -1 thiocarbamoyl Chemical group 0.000 claims description 179
- 150000001875 compounds Chemical class 0.000 claims description 61
- 229910052736 halogen Inorganic materials 0.000 claims description 33
- 150000002367 halogens Chemical class 0.000 claims description 33
- 238000002360 preparation method Methods 0.000 claims description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 21
- 239000000460 chlorine Substances 0.000 claims description 21
- 229910052801 chlorine Inorganic materials 0.000 claims description 21
- 239000011737 fluorine Substances 0.000 claims description 20
- 229910052731 fluorine Inorganic materials 0.000 claims description 20
- 239000005864 Sulphur Substances 0.000 claims description 18
- 125000001118 alkylidene group Chemical group 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 15
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
- 125000003368 amide group Chemical group 0.000 claims description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 11
- 150000003851 azoles Chemical class 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
- 125000001188 haloalkyl group Chemical group 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical group [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 8
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 7
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 7
- 229940100198 alkylating agent Drugs 0.000 claims description 7
- 239000002168 alkylating agent Substances 0.000 claims description 7
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 7
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 7
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 7
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 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
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 5
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 5
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 5
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 5
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 5
- 125000005291 haloalkenyloxy group Chemical group 0.000 claims description 5
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 5
- 229950001891 iprotiazem Drugs 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
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 5
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 5
- 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 5
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 5
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 5
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 5
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 5
- JKTORXLUQLQJCM-UHFFFAOYSA-N 4-phosphonobutylphosphonic acid Chemical compound OP(O)(=O)CCCCP(O)(O)=O JKTORXLUQLQJCM-UHFFFAOYSA-N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
- 241000607479 Yersinia pestis Species 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 229930192474 thiophene Natural products 0.000 claims description 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004666 alkoxyiminoalkyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- QFXZANXYUCUTQH-UHFFFAOYSA-N ethynol Chemical group OC#C QFXZANXYUCUTQH-UHFFFAOYSA-N 0.000 claims description 2
- 150000002240 furans Chemical class 0.000 claims description 2
- 239000002917 insecticide Substances 0.000 claims description 2
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 150000003217 pyrazoles Chemical class 0.000 claims description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 150000003233 pyrroles Chemical class 0.000 claims description 2
- 150000004867 thiadiazoles Chemical class 0.000 claims description 2
- 150000003852 triazoles Chemical class 0.000 claims description 2
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 5
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 claims 1
- 241000238631 Hexapoda Species 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- 230000002508 compound effect Effects 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 2
- 125000006193 alkinyl group Chemical group 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 239000013067 intermediate product Substances 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 239000011593 sulfur Substances 0.000 abstract 1
- 239000002585 base Substances 0.000 description 74
- 150000001721 carbon Chemical group 0.000 description 49
- 241000894006 Bacteria Species 0.000 description 36
- 230000000694 effects Effects 0.000 description 34
- 238000012360 testing method Methods 0.000 description 30
- 239000000203 mixture Substances 0.000 description 26
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 241000196324 Embryophyta Species 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 17
- 239000013543 active substance Substances 0.000 description 16
- 239000003995 emulsifying agent Substances 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
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- 150000002148 esters Chemical class 0.000 description 12
- 239000003999 initiator Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 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 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
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- 239000000725 suspension Substances 0.000 description 9
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- 125000002877 alkyl aryl group Chemical group 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
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- 150000002576 ketones Chemical class 0.000 description 7
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
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- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
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- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
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- 150000001298 alcohols Chemical class 0.000 description 4
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- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/86—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/88—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with three ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Abstract
本发明涉及通式(I)的新的肟衍生物,其中A是亚烷基,Ar是各自任意取代的亚芳基或杂亚芳基,G代表单键,杂原子任意间开的亚烷基(但是与R1连接的碳原子在任何情况下总与亚烷基链的碳原子相连)或G代表如说明书中基团,其中R3代表烷基,R1代表氢、氰基或各自任意取代的烷基、烷氧基、烷硫基、烷基氨基、二烷基氨基或环烷基,R2代表氢或烷基,Y代表氧、硫或-NH-和Z代表各自任意取代的烷基、链烯基、链炔基、环烷基、芳香基或杂环基,涉及其制备方法和其作为杀真菌剂的用途,以及新的中间体和制备它们的多种方法。
Description
本发明涉及新的肟衍生物,涉及它们的多种制备方法和它们作为杀真菌剂的用途,还涉及新的中间体和它们的多种制备方法。
已知结构上与下相似的某些肟衍生物具有杀真菌性质(参见,例如WO-A9504728)。但是,在许多情况下这些化合物的杀真菌活性不令人满意。
本发明提供通式(I)的新的肟衍生物其中A是亚烷基Ar是各自任意取代的亚芳基或杂亚芳基,G代表单键,杂原子任意间开的亚烷基(但是与R1连接的碳原子在任何情况下总与亚烷基链的碳原子相连)或G代表基团其中R3代表烷基,R1代表氢、氰基或各自任意取代的烷基、烷氧基、烷硫基、烷基氨基、二烷基氨基或环烷基,R2代表氢或烷基,Y代表氧、硫或-NH-和Z代表各自任意取代的烷基、链烯基、链炔基、环烷基、芳香基或杂环基。
在定义中,饱和或不饱和烃链例如烷基、亚烷基、链烯基或链炔基,每种情况都包括直链或支链,也包括连接的杂原子,例如烷氧基、烷硫基或烷基氨基。如果烷基或亚烷基链是被一个以上杂原子间开,它们可以相同或不同。如果烷基或亚烷基链被一个以上氧原子间开,它们彼此不相邻。
卤素通常代表氟、氯、溴或碘,也包括假卤素,例如氰基,优选氟、氯、溴或氰基,特别优选氟或氯。
芳香基代表单或多环烃,例如苯基、萘基、蒽基、菲基,优选苯基或萘基,特别优选苯基。
杂环代表饱和或不饱和杂环,也包括芳香杂环,环化物中至少一个成环原子是杂原子,即不同于碳的原子。如果环中含有多个杂原子,那么它们可以相同或不同。优选杂原子是氧、氮或硫。如果适合的话,环化物也可以与其它碳环或杂环形成稠环或桥环的多环体系。优选单环或双环体系,特别优选单环或双环芳香环体系。
环烷基代表饱和碳环化合物,可以任意与其它稠合碳环或桥环形成多环体系。
此外,还发现(方法a)通式(II)的肟与通式(III)的烷化剂反应,得到通式(I)的新的肟衍生物,其中A、Ar、Y和R2的定义同上,其中G、R1和Z的定义同上和X代表卤素、烷基磺酰氧基或任意取代的芳基磺酰氧基。
如果适合的话,在稀释剂存在下和如果适合的话,在酸受体存在下。
最后发现,通式(I)的新的肟衍生物有非常强的杀真菌活性。
如果适合的话,本发明的化合物可以以各种可能的异构体形式存在,特别是立体异构体,例如E和Z,或光学异构体。本申请要求异构体E和Z,单独的对映体,外消旋体和这些异构体的任何混合物。
本申请优选提供了通式(I)的肟衍生物,其中A代表1-6个碳原子的亚烷基,Ar代表各自任意取代的亚苯基或亚萘基,代表各自为5或6元单环或双环杂亚芳基或代表苯稠合的5或6元环杂亚芳基,其中至少一个各自代表氧、硫或氮和其它的一个或两个任意代表氮,其中优选下列可能的取代基:卤素、氰基、硝基、氨基、羟基、甲酰基、羧基、氨基甲酰基、硫代氨基甲酰基,各自为直链或支链的1-6个碳原子的烷基、烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基,各自为直链或支链的2-6个碳原子的直链或支链链烯基、链烯氧基或链炔氧基,各自为直链或支链的1-6个碳原子和1-13个相同或不同卤素原子的卤代烷基、卤代烷氧基、卤代烷硫基、卤代烷基亚磺酰基或卤代烷基磺酰基,各自为直链或支链的2-6个碳原子和1-11个相同或不同卤素原子的卤代链烯基或卤代链烯氧基,各自为直链或支链的烷基氨基、二烷基氨基、烷基羰基、烷基羰基氧基、烷氧基羰基、烷基磺酰氧基、肟基烷基或烷氧亚氨基烷基(alkoximinoalkyl),在单独的烷基部分各自有1-6个碳原子,各自为双键结合的1-6个碳原子的亚烷基或二氧亚烷基和各自任意被相同或不同取代基单或多取代,取代基选自卤素、1-4个碳原子的直链或支链烷基和1-4个碳原子和1-9个相同或不同卤素原子的直链或支链卤代烷基,G代表单键,代表被一或两个杂原子任意断开的1-5元亚烷基(但是与R1连接的碳原子在任何情况下总与亚烷基链的碳原子相连)或基团其中R3代表1-4个碳原子的烷基,R1代表氢、氰基,代表各自被卤素、氰基或C1-C4烷氧基任意取代的烷基、烷氧基、烷硫基、烷基氨基、二烷基氨基,各自的烷基有1-6个碳原子或代表各自被卤素、氰基、羧基、C1-C4烷基或C1-C4烷氧基任意取代的有3-6个碳原子的环烷基,R2代表氢或1-4个碳原子的烷基,Y代表氧、硫或-NH-和Z代表1-8个碳原子的烷基,其可任意被单取代或相同或不同的取代基多取代,取代基选自卤素、氰基、羟基、氨基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基和C1-C4烷基磺酰基(每种情况可以任意被卤素取代);代表各自多至8个碳原子的任意卤代的链烯基或链炔基;代表各自任意被单取代或相同或不同的取代基多取代的3-6个碳原子的环烷基,取代基选自卤素、氰基、羧基、苯基(其被卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基任意取代)、C1-C4烷基和C1-C4烷氧基-羰基;或代表各自被任意单取代或相同或不同取代基多取代的苯基或萘基,或代表3-7元杂环,其中至少一个代表氧、硫或氮和另外一个或两个任意代表氮,其中可能的取代基优选自下列基团:卤素、氰基、硝基、氨基、羟基、甲酰基、羧基、氨基甲酰基、硫代氨基甲酰基;各自为1-6个碳原子的直链或支链烷基、烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基;各自为2-6个碳原子的直链或支链链烯基或链烯氧基;各自为1-6个碳原子和1-13个相同或不同卤素原子的直链或支链卤代烷基、卤代烷氧基、卤代烷硫基、卤代烷基亚磺酰基或卤代烷基磺酰基;各自为2-6个碳原子和1-11个相同或不同卤素原子的直链或支链卤代链烯基或卤代链烯氧基;各自为直链或支链的烷基氨基、二烷基氨基、烷基羰基、烷基羰基氧基、烷氧基羰基或烷基磺酰氧基,在单独的烷基部分各自有1-6个碳原子;各自为双键结合的1-6个碳原子的亚烷基或二氧亚烷基和各自被任意单取代或相同或不同取代基多取代,取代基选自卤素、1-4个碳原子的直链或支链烷基和1-4个碳原子和1-9个相同或不同卤素原子的直链或支链卤代烷基;3-6个碳原子的环烷基;各自为3-7元环的杂环基或杂环基-甲基,有1-3个相同或不同的杂原子-特别是氮、氧和/或硫-或基团A1代表1-4个碳原子的烷基或1-6个碳原子的环烷基和A2代表氰基、烷氧基、烷硫基、烷基氨基、二烷基氨基或苯基取代的1-4个碳原子的烷基或2-4个碳原子的链烯基或链炔基。
本申请特别涉及通式(I)的化合物,其中A代表亚甲基、乙烷-1,1-二基、乙烷-1,2-二基、丙烷-1,1-二基、丙烷-1,2-二基、丙烷-1,3-二基、丙烷-2,2-二基、丁烷-1,2-二基、丁烷-1,3-二基或丁烷-2,3-二基,Ar代表邻亚苯基、间亚苯基或对亚苯基、呋喃二基、噻吩二基、吡咯二基、吡唑二基、三唑二基、噁唑二基、异噁唑二基、噻唑二基、异噻唑二基、噁二唑二基、噻二唑二基、吡啶二基(特别是吡啶-2,3-二基)、嘧啶二基、哒嗪二基、吡嗪二基、1,3,4-三嗪二基或1,2,3-三嗪二基,以上各基团也可任意被氟、氯、氰基、甲基、乙基、环丙基、三氟甲基、甲氧基、乙氧基、甲硫基、甲基亚磺酰基或甲基磺酰基单取代或二取代,G代表单键、亚甲基、乙烷-1,2-二基、-O-CH2-或基团其中R3代表甲基、乙基、正丙基或异丙基,R1代表氢、氰基、甲基、乙基或环丙基,R2代表氢或甲基,Y代表氧、硫或-NH-和Z代表苯基、1,2,4-噻二唑基、1,3,4-噻二唑基、1,2,4-噁二唑基、1,3,4-噁二唑基、吡啶基、嘧啶基、哒嗪基、吡嗪基、1,2,3-三嗪基、1,2,4-三嗪基、1,3,5-三嗪基或5,6-二氢-1,4,2-二噁嗪基,以上的基团可被相同或不同的取代基任意单至三取代,其中可能的取代基优选自以下:氟、氯、溴、氰基、正丁基、异丁基、仲丁基或叔丁基、甲氧基、乙氧基、正丙氧基或异丙氧基、甲硫基、乙硫基、正丙硫基或异丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基或乙基磺酰基、三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟氯甲氧基、三氟乙氧基、二氟甲硫基、三氟甲硫基、二氟氯甲硫基、三氟甲基亚磺酰基或三氟甲基磺酰基、甲氧羰基、乙氧羰基,每种情况下都与亚甲二氧基、亚乙二氧基双键连接,每种情况下都可以任意被相同或不同的取代基单至四取代,取代基包括氟、氯、甲基、三氟甲基和乙基或基团其中A1代表甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基、环丙基或环丁基和A2代表甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基、烯丙基、炔丙基、丁-2-烯-1-基、2-甲基-丙-1-烯-3-基、氰甲基、甲氧基甲基、乙氧基甲基、甲氧基乙基、乙氧基乙基、甲硫基甲基、乙硫基甲基、甲硫基乙基、乙硫基乙基、二甲氨基甲基、二甲氨基乙基、甲氨基甲基、甲氨基乙基或苄基。
本发明通式(I)的化合物中被特别优选的化合物的基团其中A代表亚甲基、乙烷-1,1-二基、乙烷-1,2-二基、丙烷-1,1-二基、丙烷-1,2-二基、丙烷-1,3-二基、丙烷-2,2-二基、丁烷-1,2-二基、丁烷-1,3-二基或丁烷-2,3-二基,Ar代表邻亚苯基、吡啶-2,3-二基或噻吩-2,3-二基,G代表单键,亚甲基、乙烷-1,2-二基、-O-CH2-或基团其中R3代表甲基,R1代表甲基,R2代表氢,Y代表氧、硫或-NH-和Z代表各自被相同或不同取代基任意单至三取代的苯基、吡啶基、嘧啶基、噻吩基或5,6-二氢-1,4,2-二噁嗪基,其中可能的取代基优选自以下:氟、氯、溴、氰基、甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基、甲氧基、乙氧基、正丙氧基或异丙氧基、甲硫基、乙硫基、正丙硫基或异丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基或乙基磺酰基、三氟甲基、二氟甲氧基、三氟甲氧基、二氟氯甲氧基、三氟乙氧基、二氟甲硫基、三氟甲硫基、二氟氯甲硫基、三氟甲基亚磺酰基或三氟甲基磺酰基、甲氧羰基、乙氧羰基,每种情况下都与亚甲二氧基、亚乙二氧基双键连接,每种情况下都可以任意被相同或不同的取代基单至四取代,取代基选自氟、氯、甲基、三氟甲基和乙基或基团其中A1代表甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基、环丙基或环丁基和A2代表甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基、烯丙基、炔丙基、丁-2-烯-1-基、2-甲基-丙-1-烯-3-基、氰甲基、甲氧基甲基、乙氧基甲基、甲氧基乙基、乙氧基乙基、甲硫基甲基、乙硫基甲基、甲硫基乙基、乙硫基乙基、二甲氨基甲基、二甲氨基乙基、甲氨基甲基、甲氨基乙基或苄基。
在本发明特别优选的化合物基团中,Ar代表邻-亚苯基。
在本发明更特别优选的化合物基团中,Y代表氧和A代表1,2-乙烷二基。
上述一般基团的定义或优选范围的基团的定义同样适用于通式(I)的最终产物和相应的起始化合物或每种制备过程所需的中间体。
这些基团所给的基团定义在单独情况下,在联合使用或上述优选联合使用的基团,在单独或联合的特别情况下也可以被其他优选范围的任何基团定义取代。
本发明的化合物实例列于表1-6:表1其中Z1代表以下取代基:表2其中Z1代表表1所示取代基。表3其中Z1代表表1所示取代基。表4其中Z1代表表1所示取代基。表5其中Z1代表表1所示取代基。表6其中Z1代表表1所示取代基。
通式(II)为进行本发明步骤a)所需的起始物肟提供了一般定义。在通式(II)中,A、Ar、Y和R2优选或特别优选的定义已经在本发明通式(I)的相关定义中作为A、Ar、Y和R2的优选或特别优选给出。
通式(II)的起始物迄今还不是已知的,作为新物质,它们也构成了本申请主题的一部分。
通式(II)的肟可以通过通式(IV)的酮化合物与羟胺或其盐反应(步骤b)得到其中A、Ar、Y和R2的定义同上,
如果合适的话,在稀释剂存在下进行,稀释剂优选醇类,例如甲醇、乙醇、正丙醇或异丙醇、正丁醇、异丁醇、仲丁醇或叔丁醇、乙二醇、丙烷-1,2-二醇、乙氧基乙醇、甲氧基乙醇、二甘醇单甲醚、二甘醇单乙醚,它们与水的混合物或纯水,和如果合适的话在碱的存在下进行,优选碱土金属的或碱金属的氢氧化物、醇盐、乙酸盐、碳酸盐或碳酸氢盐,例如甲醇钠、乙醇钠、叔丁醇钾、氢氧化钠、氢氧化钾、氢氧化铵、乙酸钠、乙酸钾、乙酸钙、乙酸铵、碳酸钠、碳酸钾、碳酸氢钾、碳酸氢钠或碳酸铵,或叔胺,例如三甲胺、三乙胺、三丁胺、N,N-二甲基苯胺、N,N-二甲基苄胺、吡啶、N-甲基哌啶、N-甲基吗啉、N,N-二甲基氨基吡啶、二氮杂双环辛烷(DABCO)、二氮杂双环壬烯(DBN)或二氮杂双环癸烯(DBU)。
通式(IV)为进行本发明步骤b)所需的起始物的酮化合物提供了一般定义。在通式(IV)中,A、Ar、Y和R2优选或特别优选的定义已经在本发明通式(I)化合物的相关定义中作为A、Ar、Y和R2的优选或特别优选给出。
通式(IV)的酮化合物迄今还不是已知的,作为新物质,它们也构成了本申请主题的一部分。
通式(IV)的酮化合物可以通过已知的方法,由通式(V)的卤代烷基化合物与二甲基亚砜(Nef反应)、乌洛托品(Sommelet反应)、氮酸(Hass反应)、氧化胺或亚硝基化合物(Krohnke反应)反应(步骤C)得到其中
A、Ar、Y和R2的定义同上,
X1代表卤素,
如果适合的话在碱存在下反应,优选碱土金属的或碱金属的氢化物、酰胺、醇盐,例如氢化钠、氨基化钠、甲醇钠、乙醇钠、叔丁醇钾,和如果适合的话在稀释剂存在下,优选酰胺,例如N,N-二甲基甲酰胺或醇类,例如甲醇、乙醇、正丙醇或异丙醇、正丁醇、异丁醇、仲丁醇或叔丁醇,反应温度为-20-150℃,优选-10-120℃。
通式(V)为进行本发明步骤C)所需的起始物卤代烷基化合物提供了一般定义。在通式(V)中,A、Ar、Y和R2优选或特别优选的定义已经在本发明通式(I)的A、Ar、Y和R2优选或特别优选的相关定义中给出。X1代表卤素和优选代表氯或溴。
通式(V)的卤代烷基化合物迄今还不是已知的,作为新物质,它们也构成了本申请主题的一部分。
E-X2(VII)其中E代表烷基羰基、芳基羰基、烷基磺酰基或芳基磺酰基和X2代表卤素。
如果适合的话在稀释剂存在下,和如果适合的话在路易斯酸存在下反应。
通式(VI)为进行本发明步骤d)所需的起始物苯氧基化合物提供了一般定义。在通式(VI)中,A、Ar、Y和R2优选或特别优选的定义已经在本发明通式(I)的A、Ar、Y和R2优选或特别优选的相关定义中给出。Ar1代表任意取代的芳基,优选代表被卤素、各自1-4个碳原子的烷基或烷氧基任意取代的苯基,特别代表苯基或2-甲基苯基、3-甲基苯基或4-甲基苯基。
通式(VI)的苯氧基化合物是已知的和/或可以通过已知的方法制备(参见,例如,WO-A9504728和DE-A19504625)。
通式(VII)为进行本发明步骤d)进一步所需的酰基卤化合物提供了一般定义。在通式(VII)中,X2代表卤素,优选代表氯或溴。E代表烷基羰基,优选乙酰基、丙酰基或新戊酰基、芳基羰基,优选苯甲酰基或甲苯甲酰基、烷基磺酰基,优选甲基磺酰基或芳基磺酰基,优选甲苯磺酰基。
进行本发明步骤C)所需的起始物,例如二甲基亚砜、乌洛托品、氮酸、氧化胺或亚硝基化合物通常是化学合成中已知的化学品。
通式(VII)的酰基卤化合物一般是化学合成法已知的化学品。
进行本发明的步骤b)和步骤e)所需的起始物羟胺或它的盐是化学合成法已知的化学品。
通式(III)提供了为进行本发明步骤a)进一步所需的烷基化剂起始物的一般定义。在通式(III)中,G和Z优选或特别优选的定义已经在本发明通式(I)的G和Z优选或特别优选的相关定义中给出。X代表卤素,优选氯、溴或碘,或烷基磺酰基,优选甲基磺酰基或任意取代的芳基磺酰基,优选4-甲苯磺酰基。
一些通式(III)的烷基化剂中一些是已知的,它们可以通过已知的方法制备(参见,例如,J.Org.Chem.,51,1,1986,109-111;J.Chem.Soc.Perkin Trans.2,1986,593-598)。
新的通式(III-a)的烷基化剂也构成了本申请主题的一部分其中R4代表烷基或环烷基,R5代表烷基,X3代表卤素和Z2代表任意取代的芳基或杂环基,优选的通式(III-a)的化合物,其中R4代表1-4个碳原子的烷基或3-6个碳原子的环烷基,R5代表1-4个碳原子的烷基,X3代表氯、溴或碘和Z2代表苯基、萘基,它们可以各自被任意单取代或被相同或不同的取代基多取代,或代表3-7元杂环,其中至少一个代表氧、硫或氮和其中另外一个或两个任意代表氮,其中可能的取代基优选自以下:卤素、氰基、硝基、氨基、羟基、甲酰基、羧基、氨基甲酰基、硫代氨基甲酰基;各自为1-6个碳原子的直链或支链烷基、烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基;各自为2-6个碳原子的直链或支链链烯基或链烯氧基;各自为1-6个碳原子和1-13个相同或不同卤素原子的直链或支链卤代烷基、卤代烷氧基、卤代烷硫基、卤代烷基亚磺酰基或卤代烷基磺酰基;各自为2-6个碳原子和1-11个相同或不同卤素原子的直链或支链卤代链烯基或卤代链烯氧基;各自为直链或支链的烷基氨基、二烷基氨基、烷基羰基、烷基羰基氧基、烷氧基羰基或烷基磺酰氧基,在单独的烷基部分各自有1-6个碳原子;各自为双键结合的1-6个碳原子的亚烷基或二氧亚烷基和各自被单取代或相同或不同取代基多取代,取代基选自卤素、1-4个碳原子的直链或支链烷基和1-4个碳原子和1-9个相同或不同卤素原子的直链或支链卤代烷基;3-6个碳原子的环烷基烷基;各自为3-7元环的杂环基或杂环基-甲基,其中的1-3个环成分是相同或不同的杂原子-特别是氮、氧和/或硫-或基团其中A3代表1-4个碳原子的烷基或1-6个碳原子的环烷基和A4代表任意被氰基、烷氧基、烷硫基、烷基氨基、二烷基氨基或苯基取代的1-4个碳原子的烷基,2-4个碳原子的链烯基或链炔基。
特别优选的通式(III-a)化合物,其中R4代表甲基、乙基或环丙基,R5代表甲基或乙基,X3代表氯或溴和Z2代表苯基、吡啶基、嘧啶基或噻吩基,各自任意被相同或不同的取代基单至三取代,其中可能的取代基优选自以下:氟、氯、溴、氰基、甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基、甲氧基、乙氧基、正丙氧基或异丙氧基、甲硫基、乙硫基、正丙硫基或异丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基或乙基磺酰基、三氟甲基、二氟甲氧基、三氟甲氧基、二氟氯甲氧基、三氟乙氧基、二氟甲硫基、三氟甲硫基、二氟氯甲硫基、三氟甲基亚磺酰基或三氟甲基磺酰基、甲氧羰基、乙氧羰基,每种情况下都与亚甲二氧基、亚乙二氧基双键连接,每种情况下都可以任意被相同或不同的取代基单至四取代,取代基包括氟、氯、甲基、三氟甲基和乙基或基团其中A3代表甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基、环丙基或环丁基和A4代表甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基、烯丙基、炔丙基、丁-2-烯-1-基、2-甲基-丙-1-烯-3-基、氰基甲基、甲氧基甲基、乙氧基甲基、甲氧基乙基、乙氧基乙基、甲硫基甲基、乙硫基甲基、甲硫基乙基、乙硫基乙基、二甲氨基甲基、二甲氨基乙基、甲氨基甲基、甲氨基乙基或苄基。
通式(III-a)的烷基化剂通过通式(VIII)的卤代酮和羟胺或其盐反应获得(步骤e))其中R4、X3和Z2的定义同上,如果适合的话在稀释剂存在下反应,优选醇类,例如甲醇、乙醇、正丙醇或异丙醇、正丁醇、异丁醇、仲丁醇或叔丁醇、乙二醇、1,2-丙二醇、乙氧基乙醇、甲氧基乙醇、二甘醇单甲醚、二甘醇单乙醚,它们与水的混合物或纯水和如果适合的话在碱存在下反应,优选碱土金属的或碱金属的氢氧化物、醇盐、乙酸盐、碳酸盐或碳酸氢盐,例如甲醇钠、乙醇钠、叔丁醇钾、氢氧化钠、氢氧化钾、氢氧化铵、乙酸钠、乙酸钾、乙酸钙、乙酸铵、碳酸钠、碳酸钾、碳酸氢钾、碳酸氢钠或碳酸铵,或叔胺,例如三甲胺、三乙胺、三丁胺、N,N-二甲基苯胺、N,N-二甲基苄胺、吡啶、N-甲基哌啶、N-甲基吗啉、N,N-二甲基氨基吡啶、二氮杂双环辛烷(DABCO)、二氮杂双环壬烯(DBN)或二氮杂双环癸烯(DBU)。
通式(III)为进行本发明步骤e)所需的起始物的卤代酮提供了一般定义。在通式(III)中,R4、X3和Z2的优选或特别优选的定义已经在本发明通式(III-a)的R4、X3和Z2优选或特别优选的相关定义中给出。
进行本发明步骤e)所需起始物通式(VIII)的卤代酮一般是化学合成中已知的化学品。
进行本发明步骤a)的合适稀释剂为所有惰性有机溶剂。优选包括脂族烃、脂环烃或芳香烃,例如石油醚、己烷、庚烷、环己烷、甲基环基烷、苯、甲苯、二甲苯或萘烷;卤代烃,例如氯苯、二氯苯、二氯甲烷、氯仿、四氯化碳、二氯乙烷或三氯乙烷;醚类,例如乙醚、二异丙醚、甲基叔丁醚、甲基叔戊醚、二噁烷、四氢呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷或茴香醚;酮类,例如丙酮、丁酮、甲基异丁基酮或环己酮;腈类,例如乙腈、丙腈、正丁腈或异丁腈或苄基腈;酰胺类,例如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胺;酯类例如乙酸甲酯或乙酸乙酯;亚砜类,例如二甲亚砜或砜类,例如环丁砜。
如果合适的话,本发明步骤a)在合适的酸受体的存在下进行。适合的酸受体是所有惯用的无机或有机碱。优选包括碱土金属的或碱金属的氢化物、氢氧化物、酰胺、醇盐、乙酸盐、碳酸盐或碳酸氢盐,例如氢化钠、氨基钠、甲醇钠、乙醇钠、叔丁醇钾、氢氧化钠、氢氧化钾、氢氧化铵、乙酸钠、乙酸钾、乙酸钙、乙酸铵、碳酸钠、碳酸钾、碳酸氢钾、碳酸氢钠或碳酸铵,或叔胺,例如三甲胺、三乙胺、三丁胺、N,N-二甲基苯胺、N,N-二甲基苄胺、吡啶、N-甲基哌啶、N-甲基吗啉、N,N-二甲基氨基吡啶、二氮杂双环辛烷(DABCO)、二氮杂双环壬烯(DBN)或二氮杂双环癸烯(DBU)。
进行本发明的步骤a)时,反应温度可以在较宽的范围内变化。一般来说,反应温度为-20-150℃,优选0-80℃。
当进行制备通式(I)化合物的步骤a)时,一般使用通式(III)的烷基化剂相对于每摩尔通式(II)的肟为1-15摩尔,优选1-8摩尔。
本发明的步骤a)、b)、c)、d)和e)一般在常压下进行。但是,也可以在加压或减压下进行反应-一般为0.1-10巴。
本发明的材料有潜在的杀微生物活性,可以用来防治不希望的微生物,例如真菌和细菌,用于农作物保护和用于材料保护。
在农作物保护方面用作杀真菌剂,用以防治根肿菌纲真菌、卵菌纲真菌、壶菌纲真菌、接合菌纲真菌、子囊菌纲真菌、担子菌纲真菌和半知菌纲真菌。
在农作物保护方面用作杀菌剂,用以防治假单胞菌科细菌、根瘤菌科细菌、肠杆菌科细菌、棒杆菌科细菌和链霉菌科细菌。
引起真菌疾病和细菌疾病的一些病原体,按照上述属名作为例子给出如下,但不以任何方式限制于此:
黄单孢杆菌属的种类,如平原黄单孢杆菌;
假单孢菌属种类,如丁香假单孢杆菌;
欧文氏菌属种类,如食粉欧文氏菌;
腐霉属种类,如远腐霉菌;
疫霉属种类,如致病疫霉菌;
假霜霉属种类,如绿草假霜霉菌或瓜类霜霉菌;
单轴霉属种类,如葡萄生单轴霉菌;
Bremia属,如Bremia lactucae,
霜霉属种类,如豌豆霜霉菌或芸苔霜霉菌;
白粉菌属种类,如草白粉菌;
单丝壳属种类,如单丝壳菌;
叉丝单囊壳属种类,如苹果白粉病菌;
黑星菌属种类,如不等黑星菌;
核腔菌属种类,如圆核腔菌或麦类核腔菌(分生孢子型:Drechslera,同物异名:长蠕孢菌属);
旋孢腔菌属种类,如禾旋孢腔菌(分生孢子型:Drechslera,同物异名:长蠕孢菌属);
单孢锈菌属种类,如疣顶单孢锈菌;
柄锈菌属种类,如隐匿柄锈菌;
Sclerotinia属种类,如Sclerotinia sclerotiorum;
腥黑粉菌属种类,如小麦网腥黑粉菌;
黑粉菌属种类,如麦散黑粉菌或燕麦散黑粉菌;
薄膜革菌属种类,如佐佐木薄膜革菌;
梨孢霉菌种类,如散粒梨孢霉菌;
镰孢菌属种类,如黄色镰孢菌;
葡萄孢属种类,如灰葡萄孢菌;
壳针孢属种类,如小麦颖枯病菌;
小球腔菌属种类,如麦小球腔菌;
尾孢属种类,如变灰尾孢菌;
交链孢属种类,如芸苔交链孢菌;和
假尾孢属种类,如曲毛假尾孢菌。
在为防治植物病害所需浓度下,植物对活性化合物的良好耐受性使得处理植物的地上部分、繁育枝和种子,和土壤成为可能。
本发明的活性化合物可以特别成功地防治谷类病害,如抗Erysiphe,防治葡萄栽培和水果和蔬菜生长过程中的疾病,例如抗黑星菌、单丝壳菌、叉丝单囊壳菌、疫霉菌和单轴霉菌种类,或防治稻类疾病,例如梨孢霉菌种类。也可成功地防治谷类疾病,;例如壳针孢菌属、核腔菌属和旋孢腔菌属。此外,本发明的化合物也可以用来增加农作物的产量。
根据其具体的物理和/或化学特性,活性化合物可以转化成常规剂型,如溶液,乳剂,悬浮剂,粉剂,泡沫剂,膏剂,颗粒剂,气雾剂,聚合物中的细微胶囊和用于种子的包衣组合物,以及ULV冷和热雾剂。
这些剂型可以用已知的方式生产,例如,将活性化合物与填充剂(即液体溶剂,压力下的液化气体)混合,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)。用水作填充剂的情况下,也可以用有机溶剂作助溶剂。作为液体溶剂,适合的主要有:芳族化合物,如二甲苯,甲苯或烷基萘,氯代芳族化合物或氯代脂族烃,如氯代苯类,氯乙烯类或二氯甲烷,脂族烃,如环己烷或石蜡,例如矿物油馏分,醇类,如丁醇或乙二醇以及醚或酯,酮类,如丙酮,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;液化气填充剂或载体是指环境温度和大气压力下是气体的液体,例如气雾抛射剂,如卤代烃以及丁烷,丙烷,氮气和二氧化碳;固体载体适合的有:磨碎的天然矿物质和高岭土,粘土,滑石,白垩,石英,硅镁土,蒙脱石或硅藻土,和磨碎的合成矿物质,如高分散二氧化硅,矾土和硅酸盐;用于颗粒剂的固体载体适合的有:例如压碎和破碎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;乳化剂和/或起泡剂适合的有: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,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;分散剂适合的有:例如,木素亚硫酸废液和甲基纤维素。
制剂中可以使用黏合剂如粉状、颗粒或乳胶形式的羧甲基纤维素和天然和合成聚合物,如阿拉伯胶,聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂,如脑磷脂和卵磷脂,和合成磷脂。其它的添加剂可以是矿物油和植物油。
也可以使用染料,如无机颜料,例如氧化铁,氧化钛和普鲁士蓝,和有机染料,如茜素染料,偶氮染料和金属酞菁染料,和微量营养素如铁、锰、硼、铜、钴、钼和锌的盐。
制剂中通常含有按重量计0.1至95%的活性化合物,优选0.5至90%本发明的活性化合物可以以其本身或以其制剂形式,或作为与已知的杀真菌剂、杀细菌剂、杀螨剂、杀线虫剂或杀虫剂的混合物的形式使用,以例如扩大作用谱,或防止抗性的产生。在许多情况下,这些混合物可以获得增效作用。
在混合物中适宜的辅助组分的例子是以下化合物:
杀真菌剂:
aldimorph、氨丙磷酸、氨丙磷酸钾、andoprim、敌菌灵、戊环唑、腈嘧菌酯、苯霜灵、麦锈灵、苯菌灵、苄烯酸、苄烯酸-异丁酯、双丙氨酰膦、乐杀螨、联苯、双苯三唑醇、灭瘟素、糠菌唑、乙嘧酚磺酸酯、丁赛特、多硫化钙、capsimycin、敌菌丹、克菌丹、多菌灵、萎锈灵、carvon、灭螨猛、灭瘟唑、苯咪唑菌、地茂散、氯化苦、百菌清、乙菌利、clozylacon、硫杂灵、霜脲氰、环唑醇、环丙嘧啶、酯菌胺、双乙氧咪唑威、双氯酚、苄氯三唑醇、dielofluanid、哒菌清、氯硝胺、乙霉威、噁醚唑、甲菌定、烯酰吗啉、烯唑醇、烯唑醇-M、二硝巴豆酸酯、二苯胺、吡菌硫、灭菌磷、二噻农、十二环吗啉、多果定、联氨噁唑酮、克瘟散、氧唑菌、乙环唑、乙嘧酚、土菌灵、噁唑酮菌、咪菌腈、氯苯嘧啶醇、腈苯唑、甲呋酰苯胺、种衣酯、拌种咯、苯锈啶、丁苯吗啉、三苯基醋酸锡、三苯基氢氧锡、福美铁、嘧菌腙、氟定胺、氟联苯菌、氟氯菌核利、喹唑菌酮、调嘧醇、氟硅唑、黄菌胺、氟酰胺、粉唑醇、灭菌丹、乙磷铝、乙磷钠、四氯苯酞、麦穗宁、呋霜灵、呋吡唑灵、二甲呋酰苯胺、呋菌唑、呋醚唑、拌种胺、谷种定、六氯苯、己唑醇、噁霉灵、抑霉唑、酰胺唑、双胍辛醋酸盐、双八胍盐、双八胍三醋酸盐、iodocarb、环戊唑醇、异稻瘟病(IBP)、异丙定、irumamycin、稻瘟灵、氯苯咪菌酮、春雷霉素、亚胺菌、铜制剂,如氢氧化铜、环烷酸铜、氯氧化铜、硫酸铜、氧化铜、喹啉铜和波尔多液、代森锰铜、代森锰锌、代森锰、meferimzone、嘧菌胺、灭锈胺、甲霜灵、metconazole、磺菌威、呋菌胺、代森联、氯苯咯菌胺、噻菌胺、米多霉素、腈菌唑、甲菌利、福美镍、间硝酞异丙酯、氟苯嘧啶醇、甲呋酰胺、噁霜灵、oxamocarb、喹菌酮、氧化萎锈灵、oxyfenthiin、多效唑、稻瘟酯、戊菌唑、戊菌隆、双氯苯磷、多马霉素、病花灵、多氧霉素、polyoxorim、烯丙异噻唑、咪鲜安、腐霉利、丙酰胺、propanosine-钠、丙环唑、丙森锌、吡嘧磷、啶斑肟、二甲嘧菌胺、咯喹酮、氯吡呋醚、唑喹菌酮、五氯硝基苯(PCNB)、硫和硫制剂、戊唑醇、叶枯酞、四氯硝基苯、调环烯、氟醚唑、噻菌灵、噻菌腈、溴氟唑菌、甲基硫菌灵、福美双、硫氰苯甲酰胺、甲基立枯磷、甲基氟磺胺、三唑酮、三唑醇、triazbutil、唑菌嗪、杨菌胺、三环唑、十三吗啉、氟菌唑、嗪氨灵、戊叉唑菌、烯效唑、稻纹散A、乙烯菌核利、烯霜苄唑、氯菌胺、代森锌、福美锌和
咪草酯G、
OK-8705、
OK-8801、
α-(1,1-二甲基乙基)-β-(2-苯氧乙基)-1H-1,2,4-三唑-1-乙醇、
α-(2,4-二氯苯基)-β-氟-β-丙基-1H-1,2,4-三唑-1-乙醇、
α-(2,4-二氯苯基)-β-甲氧基-α-甲基-1H-1,2,4-三唑-1-乙醇、
α-(5-甲基-1,3-二噁烷-5-基)-β-[[4-(三氟甲基)-苯基]-亚甲基]-1H-1,2,4-三唑-1-乙醇、
(5RS,6RS)-6-羟基-2,2,7,7-四甲基-5-(1H-1,2,4-三唑-1-基)-3-辛酮、
(E)-α-(甲氧基亚氨基)-N-甲基-2-苯氧基-苯乙酰胺、
{2-甲基-1[[[1-(4-甲基苯基)乙基]氨基]羰基]丙基}氨基甲酸-1-异丙酯、
1-(2,4-二氯苯基)-2-(1H-1,2,4-三唑-1-基)乙同-O-(苯基甲基)肟、
1-(2-甲基-1-萘基)-1H-吡咯-2,5-二酮、
1-(3,5-二氯苯基)-3-(2-丙烯基)-2,5-吡咯烷二酮、
1-[(二碘甲基)-磺酰基]-4-甲基-苯、
1-[[2-(2,4-二氯苯基)-1,3-二噁烷-2-基]-甲基]-1H-咪唑、
1-[[2-(4-氯苯基)-3-苯基环氧乙烷基]-甲基]-1H-1,2,4-三唑、
1-[1-[2-[(2,4-二氯苯基)-甲氧基]-苯基]-乙烯基]-1H-咪唑、
1-甲基-5-壬基-2-(苯甲基)-3-吡咯烷醚
2’,6’-二溴-2-甲基-4’-三氟甲氧基-4’-三氟-甲基-1,3-噻唑-5-甲酰苯胺、
2,2-二氯-N-[1-(4-氯苯基)-乙基]-1-乙基-3-甲基-环丙基甲酰胺、
2,6-二氯-5-(甲硫基)-4-嘧啶基硫氰酸酯、
2,6-二氯-N-(4-三氟甲基苄基)-苯甲酰胺、
2,6-二氯-N-[[4-(三氟甲基)-苯基]-甲基]-苯甲酰胺、
2-(2,3,3-三碘-2-丙烯基)-2H-四唑、
2-[(1-甲基乙基)磺酰基]-5-(三氯甲基)-1,3,4-噻二唑、
2-[[6-脱氧-4-O-(4-O-甲基-β-D-吡喃葡糖基)-α-D-吡喃葡萄糖基]-氨基]-4-甲氧基-1H-吡咯并[2,3-d]嘧啶-5-腈、
2-氨基丁烷、
2-溴-2-(溴甲基)-戊二腈、
2-氯-N-(2,3-二氢-1,1,3-三甲基-1H-茚-4-基)-3-吡啶甲酰胺、
2-氯-N-(2,6-二甲基苯基)-N-(异硫氰酸根合甲基)-乙酰胺、
2-苯基苯酚(OPP)、
3,4-二氯-1-[4-(二氟甲氧基)-苯基]-1H-吡咯-2,5-二酮、3,5-二氯-N-[氰基-[(1-甲基-2-丙炔基)-氧基]-甲基]-苯甲酰胺、3-(1,1-二甲基丙基-1-氧代-1H-茚-2-腈、3-[2-(4-氯苯基)-5-乙氧基-3-异噁唑烷基]-吡啶、4-氯-2-氰基-N,N-二甲基-5-(4-甲基苯基)-1H-咪唑-1-氨磺酰、4-甲基-四唑并[1,5-a]喹唑啉-5(4H)-酮、8-(1,1-二甲基乙基)-N-乙基-N-丙基-1,4-二氧螺[4,5]癸烷-2-甲胺、8-羟基喹啉硫酸盐、9H-占吨-2-[(苯基氨基)-羰基]-9-羧酰肼、双-(1-甲基乙基)-3-甲基-4-[(3-甲基苯甲酰基)氧基]-2,5-噻吩二羧酸酯、顺-1-(4-氯苯基)-2-(1H-1,2,4-三唑-1-基)-环庚醇、顺-4-3-[4-(1,1-二甲基丙基)-苯基-2-甲基丙基]-2,6-二甲基吗啉盐酸盐、[(4-氯苯基)-偶氮]-氰基乙酸乙酯、碳酸氢钾、甲基四硫醇钠盐、1-(2,3-二氢-2,2-二甲基-1H-茚-1-基)-1H-咪唑-5-羧酸甲酯、N-(2,6-二甲基苯基)-N-(5-异噁唑基羰基)-DL-丙氨酸甲酯、N-(氯乙酰基)-N-(2,6-二甲基苯基)-DL-丙氨酸甲酯、N-(2,3-二氯-4-羟基苯基)-1-甲基-环己烷酰胺、N-(2,6-二甲基苯基)-2-甲氧基-N-(四氢-2-氧代-3-呋喃基)-乙酰胺、N-(2,6-二甲基苯基)-2-甲氧基-N-(四氢-2-氧代-3-噻吩基)-乙酰胺、N-(2-氯-4-硝基苯基)-4-甲基-3-硝基-苯磺酰胺、N-(4-环己基苯基)-1,4,5,6-四氢-2-嘧啶胺、N-(4-己基苯基)-1,4,5,6-四氢-2-嘧啶胺、N-(5-氯-2-甲基苯基)-2-甲氧基-N-(2-氧代-3-噁唑烷基)-乙酰胺、N-(6-甲氧基)-3-吡啶基)-环丙酰胺、N-[2,2,2-三氯-1-[(氯乙酰基)-氨基]-乙基]-苯甲酰胺、N-[3-氯-4,5-双(2-丙炔基氧基)-苯基]-N’-甲氧基-甲亚酰胺、N-甲酰基-N-羟基-DL-丙氨酸、-钠盐、O,O-二乙基[2-(二丙基氨基)-2-氧乙基]-乙基硫代磷酰胺酯、O-甲基S-苯基硫代苯丙基磷酰胺酯、1,2,3-苯并噻二唑-7-硫代羧酸S-甲酯、
螺[2H]-1-苯并吡喃-2,1’(3’H)-异苯并呋喃]-3’-酮、
杀细菌剂:
溴硝醇、双氯酚、氯甲基吡啶、福美镍、春雷霉素、异噻菌酮、呋喃甲酸、土霉素、烯丙异噻唑、链霉素、叶枯酞、硫酸铜和其它铜制剂。
杀虫剂/杀螨剂/杀线虫剂:
齐墩螨素、乙酰甲胺磷、氟酯菊酯、棉铃威、涕灭威、甲体氯氰菊酯、双甲脒、阿维螨素、AZ60541、azadirachtin、保棉磷A、保棉磷M、三唑锡、苏芸金杆菌、4-溴-2-(4-氯苯基)-1-(乙氧基甲基)-5-(三氟甲基)-1H-吡咯-3-腈、噁虫威、丙硫克百威、杀虫蟥、氟氯氰菊酯、氟氯菊酯、BPMC、溴醚菊酯、溴硫磷、合杀威、噻嗪酮、丁酮威、丁基哒螨酮、硫线磷、甲萘威、克百威、三硫磷、丁硫克百威、杀螟丹、chloethocarb、壤虫氯磷、氯唑虫清、毒虫畏、定虫隆、氯甲硫磷、N-[(6-氯-3吡啶基)-甲基]-N’-氰基-N-甲基-乙酰亚胺、毒死蜱、甲基毒死蜱、顺式苄呋菊酯、三氟氯氰菊酯、四螨嗪、杀螟腈、乙氰菊酯、氟氯氰菊酯、氯氟氰菊酯、三环锡、氯氰菊酯、灭蝇胺、溴氰菊酯、甲基内吸磷、杀螨隆、二嗪磷、酚线磷、敌敌畏、dicliphos、百治磷、乙硫磷、除虫脲、乐果、甲基毒虫畏、二噁硫磷、乙拌磷、克瘟散、emamectin、高氰戊菊酯、乙硫苯威、乙硫磷、醚菊酯、丙线磷、乙嘧硫磷、克线磷、喹螨醚、苯丁锡、杀螟硫磷、仲丁威、苯硫威、双氧威、甲氰菊酯、fenpyrad、唑螨酯、氟啶胺、fluazuron、氟螨脲、氟氰戊菊酯、氟虫脲、氟醚菊酯、氟胺氰菊酯、地虫硫磷、安果、噻唑磷、溴醚菊酯、呋线威、六六六、庚烯磷、氟幼脲、噻螨酮、咪蚜胺、异稻瘟净、氯唑磷、异丙胺磷、叶蝉散、噁唑磷、伊维菌素、λ-三氟氯氰菊酯、lufenuron、马拉硫磷、灭蚜蜱、速灭磷、倍硫磷亚砜、蜗牛敌、虫螨畏、甲胺磷、杀扑磷、灭梭威、灭多威、速灭威、米尔倍菌素、久效磷、moxidectin、二溴磷、NC184、nitenpyram、氧乐果、杀线威、亚砜吸磷、异砜磷、对硫磷、甲基对硫磷、氯菊酯、稻丰散、甲拌磷、伏杀硫磷、亚胺硫磷、磷胺、辛硫磷、抗蚜威、甲基嘧啶硫磷、嘧啶硫磷、猛杀威、丙虫磷、残杀威、丙硫磷、发果、pymetrozin、pyrachlophos、哒嗪硫磷、反灭菊酯、除虫菊酯、哒螨酮、pyrimidifen、蚊蝇醚、蔬果磷、sebufos、silafluofen、治螟磷、sulprofos、tebufenozide、tebufenpyrad、tebuprimphos、甲丙硫磷、伏虫隆、七氟菊酯、双硫磷、特灭威、特丁磷、杀虫畏、thiafenox、thiodicarb、久效威、二甲硫吸磷、线虫磷、thuringiensin、四溴菊酯、苯赛螨、三唑磷、triazuron、敌百虫、杀虫隆、trimethacarb、蚜灭多、XMC、灭杀威、zetamethrin。
本发明活性化合物也可与其它已知活性化合物如除草剂、或与化肥和生长调节剂混合。
活性化合物可以以其原样或以其市售制剂或由其制备的使用形式使用,例如可直接使用的溶液、悬浮剂、可湿性粉剂,膏剂,可溶性粉剂,粉剂和颗粒剂。它们以常规方法使用,例如浇泼,喷雾,弥雾,撒施,喷粉,气泡,涂刷等等。此外可用超低容量方法使用化合物,或将活性化合物制剂或活性化合物本身注入土壤。也可用于处理植物的种子。
处理植物部分时,使用形式中的活性化合物浓度可在大范围内变化:通常,在按重量计1和0.0001%之间,优选在按重量计0.5和0.001%间使用。
处理种子时,通常每公斤种子需要0.001至50g,优选0.01至10g量的活性化合物。
处理土壤时,活性化合物浓度为0.00001-0.1%(重量),优选0.0001-0.02%(重量),要求使用在作用部位上。
制备实施例
将在10ml二甲基甲酰胺中的0.5g(1.9mmol)的2-[(5,6-二氢-[1,4,2]二噁嗪-3-基)-甲氧基-亚氨基-甲基]-苯甲醛肟溶液冷却至0℃,和在氩气气氛下,与0.063g(2.1mmol)的80%浓度的氢化钠悬浮液混合。将2ml二甲基甲酰胺中的0.42g(2.1mmol)1-(1-氯乙基)-4-环己基苯溶液滴加到该混合物中,然后在无冷却下搅拌4小时。将反应混合物倾倒入150ml水中并每次用100ml乙酸乙酯萃取3次。用硫酸镁干燥合并的有机相和减压浓缩。将残余物通过硅胶色谱,流动相环己烷/乙酸乙酯(3∶1)。得到0.6g(理论值的70%)2-[(5,6-二氢-[1,4,2]二噁嗪-3-基)-甲氧基亚氨基甲基]-苯甲醛O-[1-(4-环己基苯基)-乙基]肟。
1H-NMR(CDCl3,TMS):δ=1.20-1.40;1.56;1.59;1.70-1.90;2.48;3.92;
4.07-4.16;4.42-4.49;5.30;7.13-8.00 ppm.起始物的制备
实施例II-1
在氩气气氛下,20℃时,将4g(0.16mol)的2-[(5,6-二氢-[1,4,2]二噁嗪-3-基)-甲氧基亚氨基-甲基]-苯甲醛的100ml乙醇溶液与5.5g(0.08mol)氯化羟铵和8g(0.08mol)三乙胺预混合,和将此混合物在20℃搅拌2小时。将反应混合物倾倒入500ml水中并每次用100ml二氯甲烷萃取3次。用硫酸镁干燥合并的有机相和减压浓缩。将残余物通过硅胶色谱,流动相环己烷/乙酸乙酯(4∶1)。得到2.4g(理论值的57%)2-[(5,6-二氢-[1,4,2]二噁嗪-3-基)-甲氧基亚氨基甲基]-苯甲醛肟。
1H-NMR(CDCl3,TMS):δ=3.97;4.14-4.19;4.49-4.52;7.18-8.03ppm.前体的制备
将19.5g(0.14mol)N-甲基吗啉N-氧化物加到15g(0.056 mol)(2-氯甲基苯基)-(5,6-二氢-[1,4,2]二噁嗪-3-基)-甲酮O-甲基肟的150ml二甲基甲酰胺溶液中,并在120℃搅拌此混合物2小时。放冷后,将反应混合物倾倒入1000ml水中并每次用200ml乙酸乙酯萃取3次。用硫酸镁干燥合并的有机相和减压浓缩。将残余物与异丙醚一起搅拌并将所得固体抽滤出。得到10.5g(理论值的76%)2-[(5,6-二氢-[1,4,2]二噁嗪-3-基)-甲氧基亚氨基-甲基]-苯甲醛。
1H-NMR(CDCl3,TMS):δ=3.96;4.17-4.20;4.53-4.56;7.29-7.95;9.92ppm.前体的制备
经15分钟,将61.1g(0.775mol)的乙酰氯加到103.4g(0.775mol)无水氯化铝的1升二氯甲烷悬浮液中。在氩气气氛下和20℃,将105g(0.31mol)KBR5896的500ml二氯甲烷溶液滴加到此混合物中,将反应混合物温热至30℃,并另外搅拌3小时。将反应混合物倾倒入2升冰水中并每次用300ml二氯甲烷萃取3次。用硫酸镁干燥合并的有机相和减压浓缩。残余物与异丙基醚一起搅拌和抽滤出得到固体(59.1g)。减压浓缩滤液和将残余物通过硅胶色谱,流动相环己烷/乙酸乙酯(3∶1)。进一步得到4g产物。一共得63.1g(理论值的76%)的(2氯甲基-苯基)-(5,6-二氢-[1,4,2]二噁嗪-3-基)-甲基酮O-甲基肟。
1H-NMR(CDCl3,TMS):δ=3.99;4.17-4.20;4.49-4.53;7.15-7.53ppm.
将0.4g(1.52mmol)的2-[(5,6-二氢-[1,4,2]二噁嗪-3-基)-甲氧基亚氨基-甲基]-苯甲醛肟的10ml的二甲基甲酰胺溶液冷却至0℃,在氩气气氛下,与0.055g(1.82mmol)80%浓度的氢化钠悬浮液混合。将0.37g(1.52mmol)的2-溴-1-(对甲苯基)-丙烷-1-酮O-甲基肟的2ml二甲基甲酰胺溶液滴加到此混合物中,无冷却下再搅拌4小时。将反应混合物倾倒入100ml水中并每次用100ml乙酸乙酯萃取3次。用硫酸镁干燥合并的有机相和减压浓缩。将残余物通过硅胶色谱,流动相环己烷/乙酸乙酯(3∶1)。得0.42g(理论值的63%)的2-[(5,6-二氢-[1,4,2]二噁嗪-3-基)-甲氧基亚氨基-甲基]苯甲醛O-[2-甲氧基亚氨基-1-甲基-2-(对甲苯基)-乙基]肟。
1H-NMR(CDCl3,TMS):δ=1.56;1.59;2.32;3.87;3.99;4.16;4.48;5.87;
7.11-7.98ppm.起始物的制备
实施例(III-a-l)
在20℃,将2.27g(10mmol)的2-溴-1-(对甲苯基)-丙-1-酮溶解在10ml乙酸中,并与1.25g(15mmol)氯化羟铵和2.07g(15mmol)乙酸钠混合。14小时后,减压蒸馏除去溶剂,将残余物溶于100ml乙酸乙酯中和分离有机相,用50g硫酸镁干燥和浓缩。得到2.5g(理论值的99%)2-溴-1-(对甲苯基)-丙-1-酮O-甲基肟,为异构体混合物(e/z=70/30)。
1H-NMR(DMSO-d6,TMS):δ=1.69(d,3H,e异构体;1,82(d,3H,z异构体);
3.78(s,3H,z异构体);3.96(s,3H,e异构体)ppm.
通过实施例(1)的方法和按本发明制备步骤a)的一般叙述,也可以得到表7中所列的本发明通式(I-a)的化合物:表7
*)1H-NMR谱通过氘氯仿(CDCl3)或六氘二甲基亚砜(DMSO-d6)记录,四甲基硅烷(TMS)为内标。化学位移的δ值为ppm。
实施例号 | Z G R1 | NMR*: |
3456789 | 3-三氟甲基苯基 - -CH34-二氟甲氧基苯基 - -H4-氯苯基 - -CH34-甲基苯基 - -CH34-乙基苯基 - -CH34-苯氧基苯基 - -CH34-丙基苯基 - -CH3 | 1.61,D(2H);3.92;4.12,M(2H);4.46,M(2H);5.37,Q(1H);7.14-8.023.93;4.13,M(2H);4.46.M(2H);5.16;6.50,T(1H);7.10-8.001.57,D(3H);3.93;4.13,M(2H);4.46,M(2H);5.29,Q(1H);7.13-8.021.59,D(3H);2.34;3.93;4.10,M(2H);4.46,M(2H);5.29,Q(1H);7.13-8.011.23,T(3H);1.60,D(3H);2.64,Q(2H);3.93;4.10,M(2H);4.45,M(2H);5.30,Q(1H);7.13-8.001.60,D(3H);3.93;4.13,M(2H);4.47,M(2H);5.33,Q(1H);6.97-8.000.94,T(3H);1.59,D(3H);1.66,M(2H);2.57,T(2H);3.92;4.13,M(2H);4.45,M(2H);5.30,Q(1H);7.13-8.00 |
通过实施例(III-a-1)的方法和按本发明制备步骤e)的一般叙述,也可以得到下面表8中所列的本发明通式(III-a)的化合物:表8
*质谱使用实施例
实施例号 | Z2 R4 R5 X3 | phys.data |
(III-a-2)(III-a-3)(III-a-4) | 2-氟苯基 -CH3 -CH3 Br4-叔丁基苯基 -CH3 -CH3 Br3-三氟甲基苯基 -CH3 -CH3 Br | MS*:m/e=259,262(M+)MS*:m/e=297.299(M+)MS*:m/e=309,311(M+) |
实施例1梨孢霉菌试验(水稻)/保护性溶剂: 12.5份(重量)丙酮乳化剂:0.3份(重量)烷芳基聚乙二醇醚
为制得合适的活性化合物制剂,将1份(重量)活性化合物与规定量的溶剂混合,和将此浓溶液用水和规定量的乳化剂稀释至所需浓度。
为试验保护性活性,用活性化合物制剂喷洒在水稻幼株上直至流掉。当喷洒层干后,用散粒梨孢霉菌孢子水悬浮液接种植物。接着将试验植物移入100%相对大气湿度和25℃的温室中。
培养4天后进行评价。
0%是指无作用,100%是指完全防治。
在此试验中,例如制备实施例5,6,7,8,9,10和11的化合物显示了活性,当典型地活性化合物浓度为0.05%时,效果是100%。使用同样的活性化合物浓度,制备实施例1的效果是90%。
实施例2疫霉菌试验(西红柿)/保护性溶剂: 47份(重量)丙酮乳化剂:3份(重量)烷芳基聚乙二醇醚
为制得合适的活性化合物制剂,将1份(重量)活性化合物与规定量的溶剂和乳化剂混合,和将此浓溶液用水稀释至所需浓度。
为试验保护性活性,以规定的用量将活性化合物制剂喷洒在幼株上。当喷洒层干后,用致病疫霉菌孢子水悬浮液接种植物。然后将试验植物移入约100%相对大气湿度和20℃的培养箱中。
培养3天后进行评价。0%是指无作用,100%是指完全防治。
在此试验中,例如制备实施例9,10和11的化合物显示了活性,当典型地活性化合物用量为100g/公顷时,相对与未经处理的对照组,防治效果是91-93%。
实施例3单轴霉菌试验(葡萄)/保护性溶剂: 47份(重量)丙酮乳化剂:3份(重量)烷芳基聚乙二醇醚
为制得合适的活性化合物制剂,将1份(重量)活性化合物与规定量的溶剂和乳化剂混合,和将此浓溶液用水稀释至所需浓度。
为试验保护性活性,以规定的用量将活性化合物制剂喷洒在幼株上。当喷洒层干后,用葡萄生单轴霉菌孢子水悬浮液接种植物。然后将试验植物移入约100%相对大气湿度和20℃的培养箱中培养1天。接着将试验植物移入约90%相对大气湿度和21℃的温室中放5天。然后润湿植物和在培养箱中放1天。
培养6天后进行评价。0%是指无作用,100%是指完全防治。
在此试验中,例如制备实施例5,6,7,8,9,10和11的化合物制剂显示了活性,当典型地活性化合物用量为100g/公顷时,相对与未经处理的对照组,防治效果是99-100%。
实施例4叉丝单囊壳菌试验(苹果)/保护性溶剂: 47份(重量)丙酮乳化剂:3份(重量)烷芳基聚乙二醇醚
为制得合适的活性化合物制剂,将1份(重量)活性化合物与规定量的溶剂和乳化剂混合,和将此浓溶液用水稀释至所需浓度。
为试验保护性活性,以规定的用量将活性化合物制剂喷洒在幼株上。当喷洒层干后,用苹果白粉病菌孢子水悬浮液接种植物。然后将试验植物移入约23℃和相对大气湿度70%的温室中培养。
培养10天后进行评价。0%是指无作用,100%是指完全防治。
在此试验中,例如制备实施例3和9的化合物显示了活性,当典型地活性化合物用量为10g/公顷时,相对与未经处理的对照组,防治效果是94-98%。
实施例5单丝壳菌试验(黄瓜)/保护性溶剂: 47份(重量)丙酮乳化剂:3份(重量)烷芳基聚乙二醇醚
为制得合适的活性化合物制剂,将1份(重量)活性化合物与规定量的溶剂和乳化剂混合,和将此浓溶液用水稀释至所需浓度。
为试验保护性活性,以规定的用量将活性化合物制剂喷洒在幼株上。当喷洒层干后,用单丝壳菌(fuliginea)孢子水悬浮液接种植物。然后将试验植物移入约23℃和相对大气湿度约70%的温室中培养。
培养10天后进行评价。0%是指无作用,100%是指完全防治。
在此试验中,例如制备实施例2,3,5,6,7,9和11的化合物显示了活性,当典型地活性化合物用量为100g/公顷时,相对与未经处理的对照组,防治效果是92-100%。
实施例6黑星菌试验(苹果)/保护性溶剂:47份(重量)丙酮乳化剂:3份(重量)烷芳基聚乙二醇醚
为制得合适的活性化合物制剂,将1份(重量)活性化合物与规定量的溶剂和乳化剂混合,和将此浓溶液用水稀释至所需浓度。
为试验保护性活性,以规定的用量将活性化合物制剂喷洒在幼株上。当喷洒层干后,用不等黑星菌孢子水悬浮液培养植物和将试验植物移入约20℃和100%相对大气湿度的培养箱中培养1天。然后将试验植物移入约21℃和相对大气湿度约90%的温室中。
培养12天后进行评价。0%是指无作用,100%是指完全防治。
在此试验中,例如制备实施例1,3,5,6,7,9,10和11的化合物显示了活性,当典型地活性化合物用量为100g/公顷时,相对与未经处理的对照组,防治效果是94-100%。
实施例7白粉菌试验(大麦)/保护性溶剂:10份(重量)N-甲基-吡咯烷酮乳化剂:0.6份(重量)烷芳基聚乙二醇醚
为制得合适的活性化合物制剂,将1份(重量)活性化合物与规定量的溶剂和乳化剂混合,和将此浓溶液用水稀释至所需浓度。
为试验保护性活性,以规定的用量将活性化合物制剂喷洒在幼株上。当喷洒层干后,用草白粉菌孢子喷涂植物。然后将试验植物移入约20℃和相对大气湿度约80%的温室中加速霉胞发展。
培养7天后进行评价。0%是指无作用,100%是指完全防治。
在此试验中,例如制备实施例1,6,7,9,10和11的化合物显示了活性,当典型地活性化合物用量为250g/公顷时,相对与未经处理的对照组,防治效果是88%。
Claims (9)
1. 通式(I)的化合物其中A是亚烷基Ar是带或不带取代基的亚芳基或杂亚芳基,G代表单键,杂原子任意间开的亚烷基,但是与R1连接的碳原子在任何情况下总与亚烷基链的碳原子相连,或G代表基团其中R3代表烷基,R1代表氢、氰基或带或不带取代基的烷基、烷氧基、烷硫基、烷基氨基、二烷基氨基或环烷基,R2代表氢或烷基,Y代表氧、硫或-NH-,和Z代表带或不带取代基的烷基、链烯基、链炔基、环烷基、芳香基或杂环基。
2.权利要求1的通式(I)化合物,其中A代表1-6个碳原子的亚烷基,Ar代表带或不带取代基的亚苯基或亚萘基,代表5或6元单环或双环杂亚芳基或代表苯稠合的5或6元环杂亚芳基,其中至少一个杂原子代表氧、硫或氮和其它的一个或两个可代表氮,其中可能的取代基是:卤素、氰基、硝基、氨基、羟基、甲酰基、羧基、氨基甲酰基、硫代氨基甲酰基,各自为直链或支链的1-6个碳原子的烷基、烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基,各自为直链或支链的2-6个碳原子的直链或支链链烯基、链烯氧基或链炔氧基,各自为直链或支链的1-6个碳原子和1-13个相同或不同卤素原子的卤代烷基、卤代烷氧基、卤代烷硫基、卤代烷基亚磺酰基或卤代烷基磺酰基,各自为直链或支链的2-6个碳原子和1-11个相同或不同卤素原子的卤代链烯基或卤代链烯氧基,各自为直链或支链的烷基氨基、二烷基氨基、烷基羰基、烷基羰基氧基、烷氧基羰基、烷基磺酰氧基、肟基烷基或烷氧亚氨基烷基(alkoximinoalkyl),在单独的烷基部分各自有1-6个碳原子,各自为双键结合的1-6个碳原子的亚烷基或二氧亚烷基和各自任意被相同或不同取代基单或多取代,取代基选自卤素、1-4个碳原子的直链或支链烷基和1-4个碳原子和1-9个相同或不同卤素原子的直链或支链卤代烷基,G代表单键,代表被一或两个杂原子任意间开的1-5元亚烷基,但是与R1连接的碳原子在任何情况下总与亚烷基链的碳原子相连,或G代表基团其中R3代表1-4个碳原子的烷基,R1代表氢、氰基,代表各自被卤素、氰基或C1-C4烷氧基取代或未取代的烷基、烷氧基、烷硫基、烷基氨基、二烷基氨基,各自的烷基有1-6个碳原子或代表各自被卤素、氰基、羧基、C1-C4烷基或C1-C4烷氧基取代或未取代的有3-6个碳原子的环烷基,R2代表氢或1-4个碳原子的烷基,Y代表氧、硫或-NH-,和Z代表1-8个碳原子的烷基,其可被单取代或被相同或不同的取代基多取代,取代基选自卤素、氰基、羟基、氨基、可以被卤素取代的C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基和C1-C4烷基磺酰基;代表各自可被卤素取代的多至8个碳原子的链烯基或链炔基;代表各自可被单取代或被相同或不同的取代基多取代的3-6个碳原子的环烷基,取代基选自卤素、氰基、羧基、苯基,该苯基可被卤素、氰基、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、C1-C4烷基和C1-C4烷氧基-羰基;或代表各自可被单取代或可被相同或不同取代基多取代的苯基或萘基,或代表3-7元杂环,其中至少一个代表氧、硫或氮和另外一个或两个可代表氮,其中可能的取代基选自下列基团:卤素、氰基、硝基、氨基、羟基、甲酰基、羧基、氨基甲酰基、硫代氨基甲酰基;各自为1-6个碳原子的直链或支链烷基、烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基;各自为2-6个碳原子的直链或支链链烯基或链烯氧基;各自为1-6个碳原子和1-13个相同或不同卤素原子的直链或支链卤代烷基、卤代烷氧基、卤代烷硫基、卤代烷基亚磺酰基或卤代烷基磺酰基;各自为2-6个碳原子和1-11个相同或不同卤素原子的直链或支链卤代链烯基或卤代链烯氧基;各自为直链或支链的烷基氨基、二烷基氨基、烷基羰基、烷基羰基氧基、烷氧基羰基或烷基磺酰氧基,在单独的烷基部分各自有1-6个碳原子;各自为1-6个碳原子的亚烷基或二氧亚烷基和各自可被单取代或可被相同或不同取代基多取代,取代基选自卤素、1-4个碳原子的直链或支链烷基和1-4个碳原子和1-9个相同或不同卤素原子的直链或支链卤代烷基;3-6个碳原子的环烷基;各自为3-7元环的杂环基或杂环基-甲基,该杂环有1-3个选自氮、氧和/或硫的相同或不同的杂原子,或为基团A1代表1-4个碳原子的烷基或1-6个碳原子的环烷基和A2代表氰基、烷氧基、烷硫基、烷基氨基、二烷基氨基或苯基取代的1-4个碳原子的烷基或2-4个碳原子的链烯基或链炔基。
3.权利要求1的通式(I)化合物,其中A代表亚甲基、乙烷-1,1-二基、乙烷-1,2-二基、丙烷-1,1-二基、丙烷-1,2-二基、丙烷-1,3-二基、丙烷-2,2-二基、丁烷-1,2-二基、丁烷-1,3-二基或丁烷-2,3-二基,Ar代表邻亚苯基、间亚苯基或对亚苯基、呋喃二基、噻吩二基、吡咯二基、吡唑二基、三唑二基、唑二基、异唑二基、噻唑二基、异噻唑二基、二唑二基、噻二唑二基、吡啶二基、嘧啶二基、哒嗪二基、吡嗪二基、1,3,4-三嗪二基或1,2,3-三嗪二基,以上各基团也可任意被氟、氯、氰基、甲基、乙基、环丙基、三氟甲基、甲氧基、乙氧基、甲硫基、甲基亚磺酰基或甲基磺酰基单取代或二取代,G代表单键、亚甲基、乙烷-1,2-二基、-O-CH2-或基团其中R3代表甲基、乙基、正丙基或异丙基,R1代表氢、氰基、甲基、乙基或环丙基,R2代表氢或甲基,Y代表氧、硫或-NH-和Z代表苯基、1,2,4-噻二唑基、1,3,4-噻二唑基、1,2,4-二唑基、1,3,4-二唑基、吡啶基、嘧啶基、哒嗪基、吡嗪基、1,2,3-三嗪基、1,2,4-三嗪基、1,3,5-三嗪基或5,6-二氢-1,4,2-二嗪基,以上的基团可被相同或不同的取代基单至三取代,其中取代基选自以下:氟、氯、溴、氰基、正丁基、异丁基、仲丁基或叔丁基、甲氧基、乙氧基、正丙氧基或异丙氧基、甲硫基、乙硫基、正丙硫基或异丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基或乙基磺酰基、三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟氯甲氧基、三氟乙氧基、二氟甲硫基、三氟甲硫基、二氟氯甲硫基、三氟甲基亚磺酰基或三氟甲基磺酰基、甲氧羰基、乙氧羰基,每种情况下都与亚甲二氧基、亚乙二氧基双键连接,每种情况下都可以被相同或不同的取代基单至四取代,取代基包括氟、氯、甲基、三氟甲基和乙基或基团其中A1代表甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基、环丙基或环丁基和A2代表甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基、烯丙基、炔丙基、丁-2-烯-1-基、2-甲基-丙-1-烯-3-基、氰甲基、甲氧基甲基、乙氧基甲基、甲氧基乙基、乙氧基乙基、甲硫基甲基、乙硫基甲基、甲硫基乙基、乙硫基乙基、二甲氨基甲基、二甲氨基乙基、甲氨基甲基、甲氨基乙基或苄基。
4.权利要求1的通式(I)化合物,其中A代表亚甲基、乙烷-1,1-二基、乙烷-1,2-二基、丙烷-1,1-二基、丙烷-1,2-二基、丙烷-1,3-二基、丙烷-2,2-二基、丁烷-1,2-二基、丁烷-1,3-二基或丁烷-2,3-二基,Ar代表邻亚苯基、吡啶-2,3-二基或噻吩-2,3-二基,G代表单键,亚甲基、乙烷-1,2-二基、-O-CH2-或基团其中R3代表甲基,R1代表甲基,R2代表氢,Y代表氧、硫或-NH-,和Z代表各自可带或不带一至三个相同或不同取代基的苯基、吡啶基、嘧啶基、噻吩基或5,6-二氢-1,4,2-二;嗪基,其中取代基选自以下:氟、氯、溴、氰基、甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基、甲氧基、乙氧基、正丙氧基或异丙氧基、甲硫基、乙硫基、正丙硫基或异丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基或乙基磺酰基、三氟甲基、二氟甲氧基、三氟甲氧基、二氟氯甲氧基、三氟乙氧基、二氟甲硫基、三氟甲硫基、二氟氯甲硫基、三氟甲基亚磺酰基或三氟甲基磺酰基、甲氧羰基、乙氧羰基,
5.一种杀虫剂组合物,其特征在于含有至少一种权利要求1的通式(I)化合物。
6.一种防治害虫的方法,其特征在于权利要求1的通式(I)化合物作用于害虫和/或它们的栖息地。
8.权利要求1至5的通式(I)化合物防治害虫的用途。
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CN01116333A Pending CN1327978A (zh) | 1996-10-17 | 2001-04-06 | 肟衍生物及其作为杀真菌剂的用途 |
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CN (2) | CN1082954C (zh) |
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DE (2) | DE19642864A1 (zh) |
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JP2002534522A (ja) | 1999-01-13 | 2002-10-15 | ビーエーエスエフ アクチェンゲゼルシャフト | アザジオキサシクロアルケン並びに有害菌類及び動物害虫の駆除のためのその使用 |
AU3247900A (en) * | 1999-03-06 | 2000-09-28 | E.I. Du Pont De Nemours And Company | Amide and ester fungicides and arthropodicides |
DE19929086A1 (de) * | 1999-06-25 | 2000-12-28 | Bayer Ag | Pyrrolderivate |
EP1228050A1 (de) * | 1999-11-12 | 2002-08-07 | Basf Aktiengesellschaft | Azadioxacycloalkene |
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WO1996025406A1 (de) * | 1995-02-13 | 1996-08-22 | Bayer Aktiengesellschaft | Fungizide aza-heterocycloalkene |
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1996
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1997
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- 1997-10-06 AU AU47076/97A patent/AU4707697A/en not_active Abandoned
- 1997-10-06 BR BR9713259-4A patent/BR9713259A/pt not_active Application Discontinuation
- 1997-10-06 KR KR1019990702877A patent/KR20000048869A/ko not_active Application Discontinuation
- 1997-10-06 CN CN97198888A patent/CN1082954C/zh not_active Expired - Fee Related
- 1997-10-06 DE DE59711502T patent/DE59711502D1/de not_active Expired - Fee Related
- 1997-10-06 US US09/284,367 patent/US6271226B1/en not_active Expired - Fee Related
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- 1997-10-06 WO PCT/EP1997/005475 patent/WO1998017653A1/de not_active Application Discontinuation
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WO1995004728A1 (de) * | 1993-08-11 | 1995-02-16 | Bayer Aktiengesellschaft | Substituierte azadioxacycloalkene und ihre verwendung als fungizide |
WO1996025406A1 (de) * | 1995-02-13 | 1996-08-22 | Bayer Aktiengesellschaft | Fungizide aza-heterocycloalkene |
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EP0934289B1 (de) | 2004-04-07 |
AU4707697A (en) | 1998-05-15 |
KR20000048869A (ko) | 2000-07-25 |
DE19642864A1 (de) | 1998-04-23 |
WO1998017653A1 (de) | 1998-04-30 |
JP2001502677A (ja) | 2001-02-27 |
DE59711502D1 (de) | 2004-05-13 |
EP0934289A1 (de) | 1999-08-11 |
CN1327978A (zh) | 2001-12-26 |
BR9713259A (pt) | 2000-03-28 |
HK1023124A1 (en) | 2000-09-01 |
CN1234027A (zh) | 1999-11-03 |
US6271226B1 (en) | 2001-08-07 |
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