CN1890246A - 吡唑并嘧啶 - Google Patents
吡唑并嘧啶 Download PDFInfo
- Publication number
- CN1890246A CN1890246A CNA2004800369542A CN200480036954A CN1890246A CN 1890246 A CN1890246 A CN 1890246A CN A2004800369542 A CNA2004800369542 A CN A2004800369542A CN 200480036954 A CN200480036954 A CN 200480036954A CN 1890246 A CN1890246 A CN 1890246A
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- CN
- China
- Prior art keywords
- group
- alkyl
- carbon atom
- methyl
- represent
- Prior art date
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- APXRHPDHORGIEB-UHFFFAOYSA-N 1H-pyrazolo[4,3-d]pyrimidine Chemical class N1=CN=C2C=NNC2=C1 APXRHPDHORGIEB-UHFFFAOYSA-N 0.000 title abstract 2
- 238000000034 method Methods 0.000 claims abstract description 120
- 244000005700 microbiome Species 0.000 claims abstract description 18
- -1 heterocyclic radical Chemical class 0.000 claims description 131
- 125000004432 carbon atom Chemical group C* 0.000 claims description 88
- 150000001875 compounds Chemical class 0.000 claims description 73
- 229910052799 carbon Inorganic materials 0.000 claims description 72
- 239000002585 base Substances 0.000 claims description 64
- 238000006243 chemical reaction Methods 0.000 claims description 49
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 229910052731 fluorine Inorganic materials 0.000 claims description 40
- 229910052801 chlorine Inorganic materials 0.000 claims description 37
- 239000011737 fluorine Substances 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 36
- 239000000460 chlorine Substances 0.000 claims description 35
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 32
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 31
- OGEBRHQLRGFBNV-RZDIXWSQSA-N chembl2036808 Chemical compound C12=NC(NCCCC)=NC=C2C(C=2C=CC(F)=CC=2)=NN1C[C@H]1CC[C@H](N)CC1 OGEBRHQLRGFBNV-RZDIXWSQSA-N 0.000 claims description 29
- 239000003795 chemical substances by application Substances 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 238000002360 preparation method Methods 0.000 claims description 26
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 24
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 24
- 229910052794 bromium Inorganic materials 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 239000001301 oxygen Substances 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
- 125000001188 haloalkyl group Chemical group 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000013543 active substance Substances 0.000 claims description 10
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 235000019270 ammonium chloride Nutrition 0.000 claims description 8
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- QEJQAPYSVNHDJF-UHFFFAOYSA-N $l^{1}-oxidanylethyne Chemical compound [O]C#C QEJQAPYSVNHDJF-UHFFFAOYSA-N 0.000 claims description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims description 6
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 239000001294 propane Substances 0.000 claims description 6
- 241000790917 Dioxys <bee> Species 0.000 claims description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
- 150000001728 carbonyl compounds Chemical class 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
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 239000011630 iodine Substances 0.000 claims description 5
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 5
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 5
- 239000005864 Sulphur Substances 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 4
- 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 3
- WIHIUTUAHOZVLE-UHFFFAOYSA-N 1,3-diethoxypropan-2-ol Chemical compound CCOCC(O)COCC WIHIUTUAHOZVLE-UHFFFAOYSA-N 0.000 claims description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 150000001336 alkenes Chemical class 0.000 claims description 3
- NEHMKBQYUWJMIP-UHFFFAOYSA-N anhydrous methyl chloride Natural products ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 3
- 239000001273 butane Substances 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 3
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 229950001891 iprotiazem Drugs 0.000 claims description 3
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 3
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 3
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 3
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 claims description 2
- 230000000855 fungicidal effect Effects 0.000 claims description 2
- 239000000417 fungicide Substances 0.000 claims description 2
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 230000000749 insecticidal effect Effects 0.000 claims description 2
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 125000005936 piperidyl group Chemical group 0.000 claims description 2
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 2
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 241000196324 Embryophyta Species 0.000 description 76
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
- 230000001580 bacterial effect Effects 0.000 description 34
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 241000233866 Fungi Species 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 239000000463 material Substances 0.000 description 20
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 230000008859 change Effects 0.000 description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 15
- 241000894006 Bacteria Species 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
- 239000003960 organic solvent Substances 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- 239000002994 raw material Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical compound N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 description 12
- 240000008042 Zea mays Species 0.000 description 11
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 11
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 11
- 235000005822 corn Nutrition 0.000 description 11
- 238000004128 high performance liquid chromatography Methods 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 241000233679 Peronosporaceae Species 0.000 description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
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- 229920000742 Cotton Polymers 0.000 description 8
- 244000299507 Gossypium hirsutum Species 0.000 description 8
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
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- 235000010469 Glycine max Nutrition 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 235000011430 Malus pumila Nutrition 0.000 description 6
- 235000015103 Malus silvestris Nutrition 0.000 description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Aalpha Natural products C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 6
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- 229940031815 mycocide Drugs 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
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- 238000010626 work up procedure Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
- FJBGIXKIXPUXBY-UHFFFAOYSA-N {2-[3-(4-chlorophenyl)propyl]-2,4,4-trimethyl-1,3-oxazolidin-3-yl}(imidazol-1-yl)methanone Chemical compound C1=CN=CN1C(=O)N1C(C)(C)COC1(C)CCCC1=CC=C(Cl)C=C1 FJBGIXKIXPUXBY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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Abstract
下式的新的吡唑并嘧啶,其中,R1、R2、R3、R4、R5和R6的定义如说明书中所述,多种制备这些化合物的方法,以及其用于防治不想要的微生物的用途。
Description
本发明涉及吡唑并嘧啶,该类物质的多种制备方法,以及该类物质用于防治不想要的微生物的用途。
已知某些吡唑并嘧啶具有杀真菌性能(对比DE-A 3 130 633或FR-A2 794 745)。
然而,由于对现代杀真菌剂在生态上及经济上的要求不断提高,所述要求涉及例如作用谱、毒性、选择性、施用率、残留物的组成以及制造的便利性,并且还可能进一步涉及例如抗性问题,因此,需要不断地开发新的至少在某些方面优于现有技术的杀真菌剂。
本发明现提供下式的新的吡唑并嘧啶
其中,
R1代表氢、任选被取代的烷基、任选被取代的链烯基、任选被取代的炔基、任选被取代的环烷基,或代表任选被取代的杂环基(heterocyclyl),
R2代表氢或烷基,或者,
R1和R2和与其连接的氮原子一起代表任选被取代的杂环,
R3代表氢、卤素、任选被取代的烷基或任选被取代的环烷基,
X 代表氧原子、HN基团、HO-N基团或Z-O-N=,其中
Z代表任选被取代的烷基或芳基烷基,
或者
R7代表氢或烷基,并且
R8代表任选被取代的烷基、任选被取代的苯基,或代表任选被取代的苯基氨基,
R5代表卤素、任选被取代的烷氧基、任选被取代的烷硫基、任选被取代的烷基亚磺酰基,或代表任选被取代的烷基磺酰基,并且
R6代表任选被取代的芳基。
此外,已发现式(I)的吡唑并嘧啶可通过如下方式获得:
a)下式的氰基化合物,
其中,
R1、R2、R3、R5和R6的定义如上,
α)如合适,在稀释剂存在下,与酸和水反应,
或者,
β)在稀释剂存在下,并且如合适,在催化剂存在下,与羟胺或羟铵盐(hydroxylammonium salt)反应,
或者,
γ)在碱存在下,并且在稀释剂存在下,与氯化铵反应,
或者,
b)在稀释剂存在下,以及如合适,在催化剂存在下,
下式的羰基化合物,
其中,
R1、R2、R3、R5、R6以及R7的定义如上,
与下式(IV)的氨基化合物反应,
H2N-R8 (IV)
其中,R8的定义如上,
其中,式(IV)的氨基化合物还可以其酸加成盐(acid additionsalt)的形式使用。
最后,已发现式(I)的吡唑并嘧啶非常适于防治不想要的微生物。特别是,它们具有强烈的杀真菌活性,并且可用于农作物保护及材料保护。
根据取代基的形式,本发明的化合物可以,如合适,以多种可能的异构体的混合物形式存在,所述异构体特别指立体异构体,例如E异构体和Z异构体、苏式和赤式异构体以及旋光异构体,如果合适还可以是互变异构体。如果R6在与连接点相邻的两个原子上被不同的取代基取代,则所讨论的化合物可以以特别的立体异构体的形式,即阻转异构体(atropisomer)的形式存在。
式(I)提供了本发明的吡唑并嘧啶的总体定义。优选以下式(I)的化合物,其中
R1代表氢、具有1至6个碳原子的烷基,所述烷基可被相同或不同的选自卤素、氰基、羟基、具有1至4个碳原子的烷氧基以及具有3至6个碳原子的环烷基的取代基一取代至五取代,
R1代表具有2至6个碳原子的链烯基,所述链烯基可被相同或不同的选自卤素、氰基、羟基、具有1至4个碳原子的烷氧基以及具有3至6个碳原子的环烷基的取代基一取代至三取代,
R1代表具有3至6个碳原子的炔基,所述炔基可被相同或不同的选自卤素、氰基、具有1至4个碳原子的烷氧基以及具有3至6个碳原子的环烷基的取代基一取代至三取代,
R1代表具有3至6个碳原子的环烷基,所述环烷基可被相同或不同的选自卤素和具有1至4个碳原子的烷基的取代基一取代至三取代,
R1代表具有5或6个环原子以及1至3个杂原子的饱和或不饱和的杂环基,所述杂原子包括例如氮、氧和/或硫,其中杂环基可被选自卤素、具有1至4个碳原子的烷基、氰基、硝基和/或具有3至6个碳原子的环烷基的取代基一取代或二取代,
R2代表氢或具有1至4个碳原子的烷基,或者
R1和R2和与其相连的氮原子一起代表具有3至6个环原子的饱和或饱和的杂环,其中所述杂环还可含有作为环原子的氮、氧或硫原子,并且所述杂环可被氟、氯、溴、具有1至4个碳原子的烷基和/或具有1至4个碳原子和1至9个氟原子和/或氯原子的卤代烷基最多三取代,
R3代表氢、氟、氯、溴、碘、具有1至4个碳原子的烷基、具有1至4个碳原子和1至9个卤素原子的卤代烷基,或者代表具有3至6个碳原子的环烷基,
R4代表
X 代表氧原子、HN基团、HO-N基团或Z-O-N=,其中Z代表烷基或芳基烷基,
或者
R4代表
R7代表氢或具有1至4个碳原子的烷基,并且
R8代表具有1至4个碳原子的烷基,其中每个烷基基团可被具有1至4个碳原子的烷氧基、在烷基部分具有1至3个碳原子的烷基羰基和/或在烷氧基部分具有1至3个碳原子的烷氧基羰基一取代或二取代,或者
R8代表苯基,所述苯基可被相同或不同的选自具有1至4个碳原子的烷基、具有1至4个碳原子的烷氧基、卤素、硝基以及具有1至4个碳原子和1至5个卤素原子的卤代烷基的取代基一取代至三取代,或者
R8代表苯基氨基,所述苯基氨基可被相同或不同的选自具有1至4个碳原子的烷基、具有1至4个碳原子的烷氧基、卤素、硝基以及具有1至4个碳原子和1至5个卤素原子的卤代烷基的取代基一取代至三取代,
R5代表氟、氯、溴、具有1至4个碳原子的烷氧基、具有1至4个碳原子的烷硫基、具有1至4个碳原子的烷基亚磺酰基或具有1至4个碳原子的烷基磺酰基,并且
R6代表苯基,所述苯基可被相同或不同的选自卤素、氰基、硝基、氨基、羟基、甲酰基、羧基、氨基甲酰基、硫代氨基甲酰基的取代基一取代至四取代;
各自具有1至6个碳原子的、各自为直链或带有支链的烷基、烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基;
各自具有2至6个碳原子的、各自为直链或带有支链的链烯基或烯氧基;
各自具有1至6个碳原子和1至13个相同或不同的卤素原子的、
各自为直链或带有支链的卤代烷基、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;
各自具有2至6个碳原子和1至11个相同或不同的卤素原子的、
各自为直链或带支链的卤代链烯基或卤代烯氧基;
各自在各自的烷基部分中具有1至6个碳原子的、各自为直链或带支链的烷基氨基、二烷基氨基、烷基羰基、烷基羰基氧基(alkylcarbonyloxy)、烷氧基羰基、烷基磺酰基氧基、肟基烷基(hydroximinoalkyl)或烷氧基亚氨基烷基(alkoximinoalkyl);
具有3至6个碳原子的环烷基,
连接于2-,3-位的1,3-丙烷二基、1,4-丁烷二基、亚甲基二氧基(-O-CH2-O)或1,2-亚乙基二氧基(-O-CH2-CH2-O-),其中所述基团可被相同或不同的选自卤素、具有1至4个碳原子的烷基以及具有1至4个碳原子和1至9个相同或不同的卤素原子的卤代烷基的取代基一取代或多取代。
特别优选下述式(I)吡唑并嘧啶,其中
R1代表氢或下式的基团
其中#标记代表连接点,
R2代表氢、甲基、乙基或丙基,或者
R1和R2和与其连接的氮原子一起代表吡咯烷基、哌啶基、吗啉基、硫代吗啉基(thiomorpholinyl)、哌嗪基、3,6-二氢-1(2H)-哌啶基或四氢-1(2H)-哒嗪基,其中这些基团可被1至3个氟原子、1至3个甲基和/或三氟甲基取代,
或者
R1和R2和与其连接的氮原子一起代表下式的基团,
其中,
R′代表氢或甲基,
R″代表甲基、乙基、氟、氯或三氟甲基,
m代表数字0、1、2或3,其中,如果m代表2或3,则R″代表相同或不同的基团,
R代表甲基、乙基、氟、氯或三氟甲基,并且,
n代表数字0、1、2或3,其中,如果n代表2或3,则R代表相同或不同的基团,
R3代表氢、氟、氯、溴、碘、甲基、乙基、异丙基、环丙基、环丁基、环戊基、环己基、三氟甲基、1-三氟甲基-2,2,2-三氟乙基或七氟异丙基,
R4代表
基团,其中
X代表氧原子、HN基团、HO-N基团或Z-O-N=,其中Z代表烷基或芳基烷基,或者
R4代表
R7代表氢、甲基或乙基,并且
R8代表具有1至2个碳原子的烷基,其中每个烷基基团可被甲氧基、乙氧基、甲基羰基、乙基羰基、甲氧基羰基或乙氧基羰基取代,或者
R8代表苯基,所述苯基可被相同或不同的选自甲基、乙基、甲氧基、乙氧基、氟、氯、溴、硝基以及三氟甲基的取代基一取代至三取代,或者
R8代表苯基氨基,所述苯基氨基可被相同或不同的选自甲基、乙基、甲氧基、乙氧基、氟、氯、溴、硝基以及三氟甲基的取代基一取代至三取代,
R5代表氟、氯、溴、甲氧基、乙氧基、甲硫基、甲基亚磺酰基或甲基磺酰基,并且
R6代表苯基,所述苯基可被相同或不同的选自氟、氯、溴、氰基、硝基、甲酰基、甲基、乙基、正或异丙基、正、异、仲或叔丁基、烯丙基、炔丙基、甲氧基、乙氧基、正或异丙氧基、甲硫基、乙硫基、正或异丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基、乙基磺酰基、烯丙基氧基、炔丙基氧基、三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基、三氟乙氧基、二氟甲硫基、二氟一氯甲硫基、三氟甲硫基、三氟甲基亚磺酰基、三氟甲基磺酰基、三氯乙炔基氧基、三氟乙炔基氧基、氯烯丙基氧基、碘炔丙基氧基、甲氨基、乙氨基、正或异丙氨基、二甲氨基、二乙氨基、乙酰基、丙酰基、乙酰氧基(acetyloxy)、甲氧基羰基、乙氧基羰基、肟基甲基、肟基乙基、甲氧基亚氨基甲基、乙氧基亚氨基甲基、甲氧基亚氨基乙基、乙氧基亚氨基乙基、环丙基、环丁基、环戊基或环己基的取代基一取代至三取代,
连接于2-,3-位的1,3-丙烷二基、亚甲基二氧基(-O-CH2-O-)或1,2-亚乙基二氧基(-O-CH2-CH2-O-),其中所述基团可被相同或不同的选自氟、氯、甲基、乙基、正丙基、异丙基以及三氟甲基的取代基一取代或多取代。
本发明的化合物的尤其优选为这样的式(I)吡唑并嘧啶,其中
R1、R2、R3和R4具有以上给出的特别优选的含义,
R5代表氟、氯、溴、甲氧基或甲硫基,并且
R6代表2,4-、2,5-、或2,6-二取代的苯基或2-取代的苯基,或代
表2,4,6-三取代的苯基,可能的取代基为已在关于特别优选的定义的列举中已提及的基团。
上述基团的定义可根据需要相互结合。而且,单独的定义可能不适用。
采用3-氰基-5-氯-6-(2-氯-4-氟苯基)-7-(3,3-二甲基丁-2-基氨基)吡唑并[1,5-a]嘧啶作为原料,并采用稀硫酸作为反应成分,本发明的方法(a,变化形式α)可由下式表示:
采用3-氰基-5-氯-6-(2-氯-4-氟苯基)-7-(3,3-二甲基丁-2-基氨基)吡唑并[1,5-a]嘧啶作为原料,并且采用羟基氯化铵(hydroxylammonium chloride)作为反应成分的方法(a,变化形式β)可由下式表示:
采用3-氰基-5-氯-6-(2-氯-4-氟苯基)-7-(3,3-二甲基丁-2-基氨基)吡唑并[1,5-a]嘧啶作为原料,采用氯化铵作为反应成分,并且采用甲醇钠作为碱的方法(a,变化形式γ)可由下式表示:
采用3-甲酰基-5-氯-6-(2-氯-4-氟苯基)-7-(3,3-二甲基丁-2-基氨基)吡唑并[1,5-a]嘧啶作为原料,并且采用2,4-二硝基苯基肼作为反应成分的本发明的方法(b)可由下式表示:
式(II)提供了实施本发明的方法(a)所需要原料氰基化合物的总体定义。在该式中,R1、R2、R3、R5和R6优选具有与本发明式(I)的化合物的相关说明中已提及的这些基团的优选定义。
式(II)的氰基化合物可通过如下方式获得:
c)如合适,在稀释剂存在下,如合适,在催化剂存在下,并且,如合适,在酸受体存在下,使下式(V)的卤代吡唑并嘧啶与下式(VI)的胺反应,
其中,
R3和R6的定义如上,
X1代表卤素,并且
Y1代表卤素,
其中
R1和R2的定义如上,
并且,如合适,得到的下式的氰基化合物,
其中,
R1、R2、R3、R6和X1的定义如上,
在第二步中,如合适,在稀释剂存在下,与下式(VII)的化合物反应,
R9-Me (VII)
其中,
R9代表任选被取代的烷氧基、任选被取代的烷硫基、任选被取代的烷基亚磺酰基或者任选被取代的烷基磺酰基,并且
Me代表钠或钾。
式(V)的卤代吡唑并嘧啶是已知的,或者可通过已知的方法制备(参见DE-A 103 28 996以及PCT/EP 03/05 159)。
因此,式(V)的卤代吡唑并嘧啶可通过以下方式获得:
d)如合适,在稀释剂存在下,
使下式(VIII)的二羟基吡唑并嘧啶与卤化剂反应,
其中,
R3和R6的定义如上。
式(VIII)的二羟基吡唑并嘧啶可通过如下方式获得:
e)如合适,在稀释剂存在下,并且如合适,在强碱存在下,下式(IX)的芳基丙二酸酯与下式(X)的氨基吡唑反应,
其中,
R6定义如上,并且
R10代表烷基,
其中,
R3定义如上。
式(IX)提供了实施本发明的方法(e)所需要原料的芳基丙二酸酯的总体定义。在该式中,R6优选具有与本发明式(I)化合物的相关说明中已提及的该基团的优选定义。R10优选代表具有1至4个碳原子的烷基,特别优选甲基或乙基。
式(IX)芳基丙二酸酯是已知的,或者可通过已知方法制备(参见US-A 6 156 925)。
式(X)提供了实施本发明的方法(e)所需要原料的氨基吡唑的总体定义。在该式中,R3优选具有与本发明式(I)化合物的相关说明中已提及的该基团的优选定义。
适合用于实施本发明的方法(e)的稀释剂为所有常规惰性有机溶剂。优选使用以下有机溶剂:脂肪族、脂环族或芳香族烃,例如石油醚、己烷、庚烷、环己烷、甲基环己烷、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,例如二乙醚、二异丙醚、甲基叔丁基醚、甲基叔戊基醚、二噁烷、四氢呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷或苯甲醚;腈,例如乙腈、丙腈、正或异丁腈或苄腈;酰胺,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三胺;酯,例如乙酸甲酯或乙酸乙酯;亚砜,例如二甲基亚砜;砜,例如四氢噻吩砜;醇,例如甲醇、乙醇、正或异丙醇、正、异、仲或叔丁醇、乙二醇、丙-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;胺,例如三正丁胺;或羧酸,例如乙酸。
用于实施方法(e)的合适的强碱优选为碱土金属或碱金属的氢化物或醇盐,以及氨基碱金属。可作为实例提及的有氢化钠、氨基钠、甲醇钠、乙醇钠以及叔丁醇钾。
本专利申请中所述的方法(e)以及其他方法通常在大气压下实施。然而,还可在升高的压力下或者在降低的压力下实施一只要无高度挥发的反应组分存在。
当实施方法(e)时,反应温度可各自在较宽的范围内变化。在没有碱的情况下,所述方法通常在100℃至250℃的温度下实施,优选在120℃至200℃的温度下实施。如果存在碱,则所述方法通常在20℃至120℃的温度下实施,优选在20℃至80℃的温度下实施。
当实施方法(e)时,每mol式(IX)的芳基丙二酸酯通常使用1至15mol的,优选1至8mol的式(X)的氨基吡唑。以常规方法进行后处理。
用于实施方法(d)的合适的卤化剂为所有适于将连接到碳上的羟基基团交换为卤素的常规试剂。优选使用三氯化磷、三溴化磷、五氯化磷、磷酰氯、碳酰氯、亚硫酰氯、亚硫酰溴或其混合物。相应的式(V)的氟化物可由氯化物或氟化物通过与氟化钾反应制备。
用于实施方法(d)的合适的稀释剂为所有常用于这类卤化反应的有机溶剂。优选使用脂肪族、脂环族或芳香族烃,例如石油醚、己烷、庚烷、环己烷、甲基环己烷、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。
然而,卤化剂本身或卤化剂与上述稀释剂中的一种的混合物也可用作稀释剂。
当实施方法(d)时,反应温度可在较宽的范围内变化。总的来说,所述方法在20℃至150℃的温度下实施,优选在40℃至120℃的温度下实施。
当实施方法(d)时,每mol式(VIII)的二羟基吡唑并嘧啶分别使用过量的卤化剂。使用常规方法进行后处理。
式(V)提供了实施本发明的方法(c)所需要原料卤代吡唑并嘧啶的总体定义。在该式中,R3和R6优选具有与本发明式(I)化合物的相关说明中已提及的这些基团的优选定义。X1和Y1各自优选代表氟、氯或溴,特别优选代表氟或氯。
式(VI)提供了实施本发明的方法(c)所需要原料胺的总体定义。在该式中,R1和R2优选具有与本发明式(I)的化合物的相关说明中已提及的这些基团的优选定义。
式(VII)提供了实施本发明的方法(c)的第二步所需要反应成分的化合物的总体定义。在该式中,R9优选代表具有1至4个碳原子的烷氧基、具有1至4个碳原子的烷硫基、具有1至4个碳原子的烷基亚磺酰基或者具有1至4个碳原子的烷基磺酰基。Me还优选代表钠或钾。
特别优选式(VII)的化合物,其中R9代表甲氧基、乙氧基、甲硫基、甲基亚磺酰基或者甲基磺酰基,并且Me代表钠或钾。
式(VI)的胺以及式(VII)化合物是已知的,或者可通过已知方法制备。
适合用于实施本发明的方法(c)的第一步的稀释剂为所有常规惰性有机溶剂。优选使用卤代烃,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,例如二乙醚、二异丙醚、甲基叔丁基醚、甲基叔戊基醚、二噁烷、四氢呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷或苯甲醚;腈,例如乙腈、丙腈、正或异丁腈或苄腈;酰胺,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三胺;酯,例如乙酸甲酯或乙酸乙酯;亚砜,例如二甲基亚砜;砜,例如四氢噻吩砜。
用于实施方法(c)的第一步的合适的酸受体为所有常用于这类反应的无机或有机碱。优选使用的酸受体有碱土金属或碱金属的氢化物、氢氧化物、氨化物、醇盐、乙酸盐、碳酸盐或碳酸氢盐,例如氢化钠、氨基钠、二异丙基氨基锂、甲醇钠、乙醇钠、叔丁醇钾、氢氧化钠、氢氧化钾、乙酸钠、乙酸钾、乙酸钙、碳酸钠、碳酸钾、碳酸氢钾以及碳酸氢钠,并且还有铵化合物,例如氢氧化铵、乙酸铵以及碳酸铵,以及叔胺,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)或二氮杂双环十一碳烯(DBU)。
用于实施方法(c)的第一步的合适的催化剂为所有常用于这类反应的反应促进剂。
优选使用氟化物,例如氟化钠、氟化钾或氟化铵。
当实施方法(c)的第一步时,反应温度可在较宽的范围内变化。总的来说,所述方法在0℃至150℃的温度下实施,优选在0℃至80℃的温度下实施。
当实施方法(c)的第一步时,每mol式(V)的卤代吡唑并嘧啶通常使用0.5至10mol,优选0.8至2mol的式(VI)的胺。以常规方法进行后处理。
适合用于实施本发明的方法(c)的第二步的稀释剂为所有常规惰性有机溶剂。优选使用卤代烃,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,例如二乙醚、二异丙醚、甲基叔丁基醚、甲基叔戊基醚、二噁烷、四氢呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷或苯甲醚;腈,例如乙腈、丙腈、正或异丁腈或苄腈;酰胺,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三胺;酯,例如乙酸甲酯或乙酸乙酯;亚砜,例如二甲基亚砜;砜,例如四氢噻吩砜。
当实施方法(c)的第二步时,反应温度也可在较宽的范围内变化。总的来说,所述方法在0℃至150℃的温度下实施,优选在20℃至100℃的温度下实施。
当实施方法(c)的第二步时,每mol所讨论的式(IIa)的氰基化合物与等量或过量的式(VII)的化合物反应。以常规方法进行后处理。
用于实施方法(a,变化形式α)的合适的酸为所有适于水解腈的常规酸。优选使用无机酸,例如盐酸或硫酸。
用于实施方法(a,变化形式α)的合适的稀释剂为常规惰性有机溶剂。可作为实例提及的有醚,例如二乙醚、四氢呋喃或二噁烷。此外,水既可用作反应组分,亦可用作稀释剂。特别优选使用同时作为稀释剂和反应组分的稀的水溶酸。
当实施本发明的方法(a,变化形式α)时,反应温度可在某一范围内变化。总的来说,所述方法在0℃至60℃的温度下实施,优选在10℃至50℃的温度下实施。
当实施本发明的方法(a,变化形式α)时,每mol式(II)的氰基化合物使用等量或过量的酸和水。通过常规方法进行后处理。通常,如果合适,在预浓缩(prior concentration)后,将反应混合物与冰搅拌,并将得到的沉淀通过抽滤滤出。
用于实施本发明的方法(a,变化形式β)的合适的反应组分为羟胺或羟铵盐,例如氯化物或硫酸盐。优选使用羟基氯化铵。
用于实施本发明的方法(a,变化形式β)的合适的稀释剂为所有常规惰性有机溶剂。优选使用醇,例如甲醇、乙醇、正丙醇或异丙醇。
用于实施本发明的方法(a,变化形式β)的合适的催化剂为所有常用于这类反应的反应促进剂。优选使用酸性或碱性催化剂,例如,商品名为Amberlyst A-21的市售弱碱性离子交换剂。
当实施本发明的方法(a,变化形式β)的时,反应温度可在某一范围内变化。总的来说,所述方法在0℃至80℃的温度下实施,优选在10℃至60℃的温度下实施。
当实施本发明的方法(a,变化形式β)的时,通常,每mol式(II)的氰基化合物使用等量或过量的、优选1.1至1.5mol的羟胺或羟铵盐。通过常规方法进行后处理。通常,如合适,将反应混合物过滤,然后浓缩,并将分离出的产物纯化。
用于实施本发明的方法(a,变化形式γ)的合适的碱为所有常用于这类反应的有机碱。优选使用碱金属醇盐,例如甲醇钠或叔丁醇钾。
用于实施本发明的方法(a,变化形式γ)的合适的稀释剂为所有常用于这类反应的有机溶剂。优选使用醇,例如甲醇、乙醇、正丙醇或异丙醇。
当实施本发明的方法(a,变化形式γ)的时,反应温度也可在某一范围内变化。总的来说,所述方法在0℃至80℃的温度下实施,优选在10℃至60℃的温度下实施。
当实施本发明的方法(a,变化形式γ)的时,通常,每mol式(II)的氰基化合物使用等量或过量的氯化铵以及催化量的碱。亦通过常规方法进行后处理。在此,以这样的方式制备的式(I)的吡唑并嘧啶还可以其氯化氢加成盐的形式被分离。
式(III)提供了实施本发明的方法(b)所需要原料羰基化合物的总体定义。在该式中,R1、R2、R3、R5、R7优选具有与本发明式(I)化合物的相关说明中已提及的该基团的优选定义。
式(III)的羰基化合物可通过如下方式获得:
f)下式的氰基化合物,
其中,
R1、R2、R3、R5和R6的定义如上,
或者
α)在氯化铵水溶液存在下,并且有机稀释剂存在下,与氢化二异丁基铝反应,
或者
β)在稀释剂存在下,并且,如合适,在催化剂存在下,与下式的格利雅化合物反应,
R11-Mg-X2 (XI)
其中,
R11代表烷基,并且
X2代表氯、溴或碘,或者,
g)下式的吡唑并嘧啶,
其中,
R1、R2、R3、R5和R6的定义如上,
在催化剂和稀释剂存在下,与下式的酰卤反应
其中,
R12代表烷基,并且
Hal代表氯或溴,
或者,在催化剂和稀释剂存在下,
与下式的酸酐反应,
其中,
R12代表烷基,
或者,
h)在二甲基甲酰胺存在下,
使下式的羟基吡唑并嘧啶与磷酰氯反应,
其中,
R3和R6的定义如上,
并且,如合适,接下来与再添加的五氯化磷反应,并且,使得到的下式的卤代吡唑并嘧啶,
其中,
R3和R6的定义如上,
如合适,在催化剂存在下,如合适,在酸结合剂存在下,并且如合适,在稀释剂存在下,
与下式的胺反应
其中,
R1和R2的定义如上。
式(XI)提供了实施本发明的方法(f,变化形式β)所需要反应成分的格利雅化合物的总体定义。在该式中,R11优选代表具有1至4个碳原子的烷基,特别优选代表甲基或乙基。X2还优选代表氯、溴或碘。
用于实施方法(f,变化形式α)的合适的稀释剂为所有常规惰性有机溶剂。优选使用任选卤化的脂肪族或芳香族烃,例如甲苯、二氯甲烷、氯仿或四氯化碳。
当实施方法(f,变化形式α)时,反应温度可在某一范围内变化。总的来说,所述方法在-80℃至+20℃的温度下实施,优选在-60℃至+10℃的温度下实施。
当实施方法(f,变化形式α)时,通常每mol式(II)的氰基化合物使用等量或过量的、优选1.1至1.2mol的氢化二异丁基铝,然后添加过量的氯化铵水溶液。通过常规方法进行后处理。通常,将反应混合物酸化,分离有机相,使用几乎不与水混溶的有机溶剂萃取水相,将合并的有机相洗涤、干燥并减压浓缩。
用于实施方法(f,变化形式β)的合适的催化剂为所有常用于格利雅反应的反应促进剂。可作为实例提及的有碘化钾及碘。
用于实施方法(f,变化形式β)的合适的稀释剂为所有常用于这类反应的惰性有机溶剂。优选使用醚,例如二乙醚、二噁烷或四氢呋喃,此外还有芳香烃,例如甲苯,以及醚和芳香烃的混合物,例如甲苯/四氢呋喃。
当实施方法(f,变化形式β)时,反应温度可在某一范围内变化。通常,所述方法在-20℃至+100℃的温度下实施,优选在0℃至+80℃的温度下实施。
当实施方法(f,变化形式β)时,通常每mol式(II)的氰基化合物使用2至3mol的式(XI)的格利雅化合物。接下来通过常规方法进行水相后处理(aqueous work up)。
式(XII)提供了实施本发明的方法(g)所需要原料吡唑并嘧啶的总体定义。在这些结构式中,R1、R2、R3、R5和R6优选具有与本发明式(I)化合物的相关说明中已提及的这些基团的优选定义。
式(XII)的吡唑并嘧啶是已知的,或者可通过已知的方法制备。
式(XIII)和式(XIV)提供了实施方法(d)而需要作为反应组分的酰卤及酸酐的总体定义。在该式中,R12优选代表具有1至4个碳原子的烷基,特别优选甲基、乙基或丙基。式(XIII)中的Hal优选代表氯或溴。
式(XIII)的酰卤及式(XIV)的酸酐都是已知的,或者可通过已知方法制备。
用于实施方法(g)的合适的催化剂为所有常用于弗瑞德-克来福特反应的反应促进剂。优选使用路易斯酸,例如三氯化铝、三溴化铝以及氯化铁(III)。
用于实施方法(g)的合适的稀释剂为所有常用于这种弗瑞德-克来福特反应的惰性有机溶剂。优选使用醚,例如二乙醚、甲基叔丁基醚、二噁烷和四氢呋喃,以及二硫化碳。
当实施方法(g)时,反应温度可在某一范围内变化。通常,所述方法在-10℃至+100℃的温度下实施,优选在0℃至80℃的温度下实施。
当实施方法(g)时,通常每mol式(XII)的吡唑并嘧啶通常使用1至5mol,优选1至2mol的式(XIII)的酰卤,以及1.1至5mol,优选1.1至3mol的催化剂,或者,使用1至5mol,优选1至2mol的式(XIV)的酸酐,以及2.1至6mol,优选2.1至4mol的催化剂。通常,先在低温下添加反应组分,在最初的剧烈反应平息后,缓慢升温至回流温度。通过常规方法进行后处理。
式(XV)提供了实施本发明的方法(h)所需要原料羟基吡唑并嘧啶的总体定义。在该式中,R3和R6优选具有与本发明式(I)化合物的相关说明中已提及的这些基团的优选定义。
当使用其中的CN基团替换为氢原子的式(X)的氨基吡唑时,式(XV)的羟基吡唑并嘧啶可由方法(e)制备。
方法(h)的第一步在Vilsmeier配方的条件下实施,即在存在二甲基甲酰胺时借助于磷酰氯实施。此时,也可添加五氯化磷作为氯化剂。
当实施方法(h)的第一步时,反应温度可在较宽的范围内变化。通常,所述方法在-10℃至+150℃的温度下实施,优选在0℃至120℃的温度下实施。
当实施方法(h)的第一步时,通常每mol式(XV)的羟基吡唑并嘧啶使用2至5mol的二甲基甲酰胺、5至15mol的磷酰氯,并且,如合适,使用0至2mol的五氯化磷。通过常规方法进行后处理。
用于实施方法(h)第二步的合适的式(VI)的胺和催化剂、酸结合剂以及稀释剂为在方法(c)第一步的有关说明中已经提及的化合物。还可采用方法(c)的第一步中相应的反应温度及其他反应条件。
式(IV)提供了实施本发明的方法(b)而需要作为反应组分的氨基化合物的总体定义。在该式中,R8优选具有在本发明式(I)的化合物的有关说明中已提及的该基团的优选定义。式(IV)的氨基化合物还可以其酸加成盐的形式使用。在此,优选的盐为通过氯化氢或硫酸加成而形成的盐。
式(IV)的氨基化合物和其酸加成盐都是已知的,或者可通过已知的方法制备。
用于实施本发明的方法(b)的合适的稀释剂为所有常规惰性有机溶剂。优选使用醇,例如甲醇、乙醇、正丙醇或异丙醇,还优选烃,例如苯或甲苯。
用于实施本发明的方法(b)的合适的催化剂为所有常用于这类反应的反应促进剂。优选使用酸性催化剂,例如硫酸或对甲苯磺酸,或者碱性催化剂,例如商品名为Amberlyst A-21的市售弱碱性离子交换剂。
当实施本发明的方法(b)时,反应温度可在较宽的范围内变化。通常,所述方法在0℃至150℃的温度下实施,优选在10℃至130℃的温度下实施。
当实施本发明的方法(b)时,通常每mol式(III)的羰基化合物使用等量或过量的,优选1.0至1.5mol的式(IV)的氨基化合物或其酸加成盐。通过常规方法进行后处理。
本发明的物质具有有效的杀微生物活性,可在作物保护和材料保护中用于防治不想要的微生物,例如真菌和细菌。
杀真菌剂可用于在农作物保护中防治根肿菌(Plasmodiophoromycete)、卵菌(Oomycete)、壶菌(Chytridiomycete)、接合菌(Zygomycete)、子囊菌(Ascomycete)、担子菌(Basidiomycete)及半知菌(Deuteromycete)。
杀细菌剂可用于在农作物保护中防治假单孢菌(Pseudomonadaceae)、根瘤菌(Rhizobiaceae)、Enterobateriaceae、Corynebacteriaceae以及链霉菌(Streptomycetaceae)。
以示例而非限制的方式列举一些归入以上所列菌类的引起真菌及细菌疾病的病原体:
黄单胞(Xanthomonas)菌种,例如野油菜黄单胞菌水稻致病变种(Xanthomonas campestris pv.oryzae);
假单胞(Pseudomonas)菌种,例如丁香假单胞菌黄瓜致病变种(Pseudomonas syringae pv.lachrymans);
欧文氏(Erwinia)菌种,例如解淀粉欧文氏菌(Erwinia amylovora);
腐霉(Pythium)菌种,例如终极腐霉(Pythium ultimum);
疫霉(Phytophthora)菌种,例如致病疫霉(Phytophthorainfestans);
假霜霉(Pseudoperonospora)菌种,例如草假霜霉(Pseudoperonospora humuli)或古巴假霜霉(Pseudoperonosporacubensis);
轴霜霉(Plasmopara)菌种,例如葡萄生轴霜霉(Plasmoparaviticola);
盘霜霉(Bremia)菌种,例如莴苣盘霜霉(Bremia lactucae);
霜霉(Peronospora)菌种,例如豌豆霜霉(Peronospora pisi)或十字花科霜霉(P.brassicae);
白粉菌(Erysiphe)菌种,例如禾谷白粉菌(Erysiphe graminis);
单囊壳属(Sphaerotheca)菌种,例如凤仙花单囊壳(Sphaerothecafuliginea);
叉丝单囊壳属(Podosphaera)菌种,例如白叉丝单囊壳(Podosphaeraleucotricha);
黑星菌属(Venturia)菌种,例如苹果黑星病菌(Venturiainaequalis);
核腔菌属(Pyrenophora)菌种,例如圆核腔菌(Pyrenophora teres)或麦类核腔菌(P.graminea)(分生孢子形式:Drechslera,syn:Helminthosporium);
旋孢腔菌属(Cochliobolus)菌种,例如禾旋孢腔菌(Cochliobolussativus)(分生孢子形式:Drechslera,syn:Helminthosporium);
单胞锈菌属(Uromyces)菌种,例如疣顶单胞锈菌(Uromycesappendiculatus);
柄锈菌(Puccinia)菌种,例如隐匿柄锈菌(Puccinia recondita);
核盘菌属(Sclerotinia)菌种,例如核盘菌(Sclerotiniasclerotiorum);
腥黑粉菌属(Tilletia)菌种,例如小麦网腥黑粉菌(Tilletiacaries);
黑粉菌(Ustilago)菌种,例如裸黑粉菌(Ustilago nuda)或燕麦黑粉菌(Ustilago avenae);
薄膜革菌属(Pellicularia)菌种,例如佐佐木薄膜革菌(Pellicularia sasakii);
梨孢(Pyricularia)菌种,例如稻梨孢(Pyricularia oryzae);
镰孢属(Fusarium)菌种,例如黄色镰孢(Fusarium culmorum);
葡萄孢属(Botrytis)菌种,例如灰葡萄孢(Botrytiscinerea);
壳针孢属(Septoria)菌种,例如颖枯壳针孢(Septorianodorum);
小球腔菌属(Leptosphaeria)菌种,例如Leptosphaeria nodorum;
尾孢属(Cercospora)菌种,例如变灰尾孢(Cercospora canescens);
链格孢属(Alternaria)菌种,例如芸薹链格孢(Alternariabrassicae);
假小尾孢属(Pseudocercosporella)菌种,例如小麦基腐病菌(Pseudocercosporella herpotrichoides)。
本发明的活性化合物还在植物中显示出强烈的激发作用(invigorating action)。因此,它们适于活化植物内部的防御性能以抵抗不想要的微生物的侵袭。
在本发明中,植物激发(抗性诱发)化合物应被理解为这样的物质,它们能够激发植物的防御系统,从而,当经处理的植物之后被不想要的微生物接种时,所述植物表现出对上述微生物显著的抵抗性。
在本发明中,不想要的微生物应被理解为植物致病真菌、细菌以及病毒。因此,本发明的化合物可用于在处理后的某段时间内保护植物抵抗所述病原体的侵袭。所获得的保护作用的时间通常为自以活性化合物处理植物起1至10天,优选1至7天。
本发明的活性化合物在防治植物病害所需浓度下具有的良好的植物耐受性,这就使得可对植物的地上部分、离体繁殖株(propagationstock)、种子以及土壤进行处理。
本发明的活性化合物能够以特别好的效果防治谷类疾病,例如防治白粉菌属种(Erysiphe),以及葡萄栽培和水果、蔬菜栽培中出现的疾病,例如防治葡萄孢属种(Botrytis)、黑星菌属种(Venturia)、单丝壳属种(Sphaerotheca)和叉丝单囊壳属种(Podosphaeva)。
本发明的活性化合物还适于提高农作物的产量。此外,它们还表现出低毒性以及良好的植物耐受性。
如果合适,本发明的活性化合物还可以在某些浓度和施用率下用作除草剂,以调节植物生长,并防治动物害虫。如果合适,它们还可用作合成其它活性化合物的中间体或前体。
所有的植物及植物部位(part)均可依据本发明来处理。本发明中植物的含义应理解为所有的植物及植物种群,例如需要的及不需要的野生植物或农作物植物(包括自然存在的农作物植物)。农作物植物可以是通过常规植物育种及优选法,或通过生物技术及基因工程,或通过所述方法的结合而获得的植物,包括转基因植物,也包括受或不受植物种苗权保护的植物品种。植物部位的含义应理解为植物所有的地上和地下部位以及植物器官,例如芽、叶、花及根,可提及的实例为叶、针叶(needle)、茎、干、花、子实体、果实、种子、根、块茎及根茎。植物部位还包括采收物和无性及有性繁殖物,例如插条、块茎、根茎、侧枝及种子。
本发明的使用活性化合物对植物及植物部位进行的处理,依据常规处理方法直接进行或使活性化合物作用于其环境、生境或贮存区域,所述常规处理方法包括例如浸泡、喷雾、蒸发、弥雾(atomizing)、撒播、涂抹(brushing-on),在繁殖物、特别是种子的情况下,也可涂布一层或多层。
在材料的保护中,本发明的化合物可用于保护工业材料免受不想要的微生物的侵染及破坏。
本发明中的工业材料的含义应理解为已制成准备用于工业的非活体材料。例如,拟由本发明的活性化合物保护以免受微生物改变或破坏的工业材料可为粘合剂、胶料、纸张及板材、织物、皮革、木材、漆及塑料制品、冷却润滑剂(cooling lubricant)及其它可受微生物侵染或破坏的材料。可被微生物繁殖损害的生产工厂部件,例如冷却水回路,亦在可保护材料的范围内。在本发明范围内可提及的工业材料优选为粘合剂、胶料、纸张及板材、皮革、木材、漆、冷却润滑剂及传热液体,尤其优选木材。
可提及的可使工业材料发生劣化或改变的微生物为,例如细菌、真菌、酵母菌、藻类及粘液生物(slime organism)。本发明的活性化合物优选作用于真菌,特别是霉菌、木材退色真菌及木腐真菌(担子菌),以及粘液生物及藻类。
可列举以下各属的微生物作为实例:
链格孢属(Alternaria),例如链格孢(Alternaria tenuis),
曲霉属(Aspergillus),例如黑曲霉(Aspergillus ningar),
毛壳菌(Chaetomium),例如球毛壳菌(Chaetomium globosum),
粉革菌属(Coniophora),例如Coniophora puetana,
香菇属(Lentinus),例如虎皮香菇菌(Lentinus tigrinus),
青霉属(Penicillium),例如灰绿青霉(Penicillium glaucum),
多孔菌(Polyporus),例如杂色多孔菌(Polyporus versicolor),
短梗霉属(Aureobasidium),例如出芽短梗霉(Aureobasidiumpullulans),
核茎点属(Sclerophoma),例如Sclerophoma pityophila,
木霉属(Trichoderma),例如绿色木霉(Trichoderma viride),
埃希氏菌属(Escherichia),例如大肠埃希氏菌(Escherichiacoli),
假单胞菌属(Pseudomonas),例如铜绿假单胞菌(Pseudomonasaeruginosa),
葡萄球菌属(Staphylococcus),例如金黄色葡萄球菌(Staphylococcus aureus)。
依据其具体的物理和/或化学特性,本发明的活性化合物可转化为常规制剂,例如溶液、乳剂、悬浮剂、粉剂、泡沫、膏剂、颗粒剂、气雾剂、聚合物与种子包衣(coating)组合物中的微胶囊剂以及ULV冷却与加温弥雾(fogging)制剂。
所述制剂以已知方式制备,例如将活性化合物与填充剂(extender)混合,即与液体溶剂、加压液化气和/或固体载体混合,同时可任选使用表面活性剂,即乳化剂和/或分散剂和/或发泡剂。如果使用的填充剂为水,还可使用例如有机溶剂作为辅助溶剂。适合的液体溶剂主要有:芳香族化合物,例如二甲苯、甲苯或烷基萘;氯化芳香族化合物或氯化脂肪烃,例如氯苯、氯乙烯或二氯甲烷;脂肪烃,例如环己烷或石蜡,如石油馏分;醇,例如丁醇或乙二醇及其醚及酯;酮,例如丙酮、甲乙酮、甲基异丁基酮或环己酮;强极性溶剂,例如二甲基甲酰胺或二甲基亚砜;或水。液化气填充剂或载体的含义应理解为在标准温度及大气压下为气态的液体,例如气溶胶喷雾剂,例如卤代烃,或丁烷、丙烷、氮气及二氧化碳。适合的固体载体为:例如粉碎的天然矿物,例如高岭土、粘土、滑石粉、白垩、石英、凹凸棒石、蒙脱石或硅藻土;以及粉碎的合成矿物,例如细分散二氧化硅、氧化铝及硅酸盐。适用于颗粒剂的固体载体为:例如粉碎并分级的天然岩石,例如方解石、浮石、大理石、海泡石及白云石;或合成的无机及有机粉颗粒,以及有机物颗粒,例如锯木屑、椰壳、玉米穗轴及烟草茎。适合的乳化剂和/或发泡剂为:例如非离子及阴离子乳化剂,例如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚,例如烷基芳基聚乙二醇醚、烷基磺酸盐、烷基硫酸盐、芳基磺酸盐,或蛋白质水解产物。适合的分散剂为:例如木素亚硫酸盐废液及甲基纤维素。
制剂中可使用增粘剂,例如羧甲基纤维素,以及粉末、颗粒或胶乳形式的天然及合成聚合物,例如阿拉伯树胶、聚乙烯醇及聚乙酸乙烯酯,或天然磷脂,例如脑磷脂及卵磷脂,以及合成磷脂。其它添加剂可为矿物油及植物油。
可使用着色剂,例如无机颜料,例如氧化铁、氧化钛及普鲁士蓝,以及有机染料,例如茜素染料、偶氮染料及金属酞菁染料,以及微量营养物,例如铁盐、锰盐、硼盐、铜盐、钴盐、钼盐及锌盐。
制剂一般包括0.1至95重量百分比的活性化合物,优选0.5至90重量百分比。
本发明的活性化合物可以其本身或其制剂的形式使用,还可以与已知的杀真菌剂、杀细菌剂、杀螨剂、杀线虫剂或杀昆虫剂混合使用,以拓宽例如其作用谱或防止抗性的产生。在很多情况下,获得了协同效应,即混合物的活性大于单独组分的活性。
合适的混合组分有例如以下化合物:
杀真菌剂:
2-苯基苯酚、8-羟基喹啉硫酸盐、acibenzolar-S-methyl、aldimorph、amidoflumet、氨丙膦酸(ampropylfos)、氨丙膦酸钾、andoprim、敌菌灵(anilazine)、戊环唑(azaconazole)、腈嘧菌酯(azoxystrobin)、苯霜灵(benalaxyl)、benalaxyl-M、麦锈灵(benodanil)、苯菌灵(benomyl)、异丙基-benthiavalicarb、苄烯酸(benzamacril)、异丁基苄烯酸、双丙氨膦(bilanafos)、乐杀螨(binapacryl)、联苯、双苯三唑醇(bitertanol)、灭瘟素(blasticidin-S)、啶酰菌胺(boscalid)、糠菌唑(bromuconazole)、磺嘧菌灵(bupirimate)、粉并定(buthiobate)、丁胺、多硫化钙、卡巴西霉素(capsimycin)、敌菌丹(captafol)、克菌丹(captan)、多菌灵(carbendazim)、萎锈灵(carboxin)、氯环丙酰胺(carpropamid)、香芹酮(carvone)、灭螨猛(chinomethionat)、灭瘟唑(chlobenthiazone)、苯咪唑菌(chlorfenazole)、地茂散(chloroneb)、百菌清(chlorothalonil)、乙菌利(chlozolinate)、clozylacon、氰霜唑(cyazofamid)、环氟菌胺(cyflufenamid)、清菌脲(cymoxanil)、环唑醇(cyproconazole)、嘧菌环胺(cyprodinil)、酯菌胺(cyprofuram)、Dagger G、双乙氧咪唑威(debacarb)、抑菌灵(dichlofluanid)、二氯萘醌(dichlone)、双氯酚(dichlorophen)、diclocymet、哒菌清(diclomezine)、氯硝胺(dicloran)、乙霉威(diethofencarb)、噁醚唑(difenoconazole)、氟嘧菌胺(diflumetorim)、甲菌定(dimethirimol)、烯酰吗啉(dimethomorph)、dimoxystrobin、烯唑醇(diniconazole)、烯唑醇-M(diniconazole-M)、敌螨普(dinocap)、二苯胺(diphenylamine)、双吡硫翁(dipyrithione)、灭菌磷(ditalimfos)、二氰蒽醌(dithianon)、dodine、敌菌酮(drazoxolon)、克瘟散(edifenphos)、氧唑菌(epoxiconazole)、韩乐宁(ethaboxam)、乙菌定(ethirimol)、氯唑灵(etridiazole)、噁唑酮菌(famoxadone)、咪唑菌酮(fenamidone)、菌拿灵(fenapanil)、异嘧菌醇(fenarimol)、腈苯唑(fenbuconazole)、甲呋酌苯胺(fenfuram)、环酰菌胺(fenhexamid)、种衣酯(fenitropan)、稻瘟酰胺(fenoxanil)、拌种咯(fenpiclonil)、苯锈啶(fenpropidin)、丁苯吗啉(fenpropimorph)、福美铁(ferbam)、氟啶胺(fluazinam)、flubenzimine、氟噁菌(fludioxonil)、氟联苯菌(flumetover)、氟吗啉(flumorph)、氟氯菌核利(fluoromide)、氟嘧菌酯(fluoxastrobin)、喹唑菌酮(fluquinconazole)、呋嘧醇(flurprimidol)、氟硅唑(flusilazole)、磺菌胺(flusulfamide)、氟酰胺(flutolanil)、粉唑醇(flutriafol)、灭菌丹(folpet)、藻菌磷(fosetyl-A1)、藻菌磷钠(fosetyl-sodium)、麦穗宁(fuberidazole)、呋氨丙灵(furalaxyl)、呋吡唑灵(furametpyr)、灭菌胺(furcarbanil)、拌种胺(furmecyclox)、双胍盐(guazatine)、六氯苯(hexachlorobenzene)、己唑醇(hexaconazole)、土菌消(hymexazole)、烯菌灵(imazalil)、酰胺唑(imibenconazole)、双胍辛胺乙酸盐(iminoctadine triacetate)、克热净(烷苯磺酸盐)(iminoctadine tris(albesil))、iodocarb、环戊唑醇(ipconazole)、异稻瘟净(iprobenfos)、异丙定(iprodione)、缬霉威(iprovalicarb)、人间霉素(irumamycin)、稻瘟灵(isoprothiolane)、氯苯咪菌酮(isovaledione)、春雷霉素(kasugamycin)、亚胺菌(kresoxim-methyl)、代森锰锌(mancozeb)、代森锰(maneb)、meferimzone、嘧菌胺(mepanipyrim)、丙氧灭锈胺(mepronil)、甲霜灵(metalaxyl)、精甲霜灵(metalaxyl-M)、环戊唑菌(metconazole)、磺菌威(methasulfocarb)、甲呋菌胺(methfuroxam)、代森联(metiram)、叉氨苯酰胺(metominostrobin)、噻菌胺(metsulfovax)、米多霉素(mildiomycin)、腈菌唑(myclobutanil)、甲菌利(myclozolin)、多马霉素(natamycin)、nicobifen、异丙消(nitrothal-isopropyl)、noviflumuron、氟苯嘧啶醇(nuarimol)、甲呋酰胺(ofurace)、orysastrobin、噁霜灵(oxadixyl)、喹菌酮(oxolinic acid)、oxpoconazole、氧化萎锈灵(oxycarboxin)、oxyfenthiin、多效唑(paclobutrazol)、稻瘟酯(pefurazoate)、戊菌唑(penconazole)、戊菌隆(pencycuron)、双氯苯磷(phosdiphen)、四氯苯酞(phthalide)、啶氧菌酯(picoxystrobin)、粉病灵(piperalin)、多抗霉素(polyoxins)、polyoxorim、噻菌灵(probenazole)、丙氯灵(prochloraz)、杀菌利(procymidone)、百维灵(propamocarb)、propanosine-sodium、丙环唑(propiconazole)、丙森锌(propineb)、proquinazid、prothioconazole、吡唑醚菌酯(pyraclostrobin)、定菌磷(pyrazophos)、啶斑肟(pyrifenox)、二甲嘧菌胺(pyrimethanil)、咯喹酮(pyroquilon)、氯吡呋醚(pyroxyfur)、pyrrolenitrine、唑喹菌酮(quinconazole)、喹氧灵(quinoxyfen)、五氯硝基苯(quintozene)、硅氟唑(simeconazole)、螺噁茂胺(spiroxamine)、硫、戊唑醇(tebuconazole)、叶枯酞(tecloftalam)、四氯硝基苯(tecnazene)、tetcyclacis、氟醚唑(tetraconazole)、涕必灵(thiabendazole)、噻菌腈(thicyofen)、溴氟唑菌(thifluzamide)、甲基托布津(thiophanate-methyl)、福美双(thiram)、tioxymid、甲基立枯磷(tolclofos-methyl)、对甲抑菌灵(tolylfluanid)、三唑酮(triadimefon)、唑菌醇(triadimenol)、丁三唑(triazbutil)、唑菌嗪(triazoxide)、tricyclamide、三环唑(tricyclazole)、克啉菌(tridemorph)、肟菌酯(trifloxystrobin)、氟菌唑(triflumizole)、嗪氨灵(triforine)、戊叉唑菌(triticonazole)、烯效唑(uniconazole)、有效霉素A(validamycinA)、烯菌酮(vinclozolin)、代森锌(zineb)、福美锌(ziram)、苯酰菌胺(zoxamide)、(2S)-N-[2-[4-[[3-(4-氯苯基)-2-丙炔基]氧]-3-甲氧基苯基]乙基]-3-甲基-2-[(甲基磺酰基)氨基]丁酰胺、1-(1-萘基)-1H-吡咯-2,5-二酮、2,3,5,6-四氯-4-(甲基磺酰基)吡啶、2-氨基-4-甲基-N-苯基-5-噻唑甲酰胺、2-氯-N-(2,3-二氢-1,1,3-三甲基-1H-茚-4-基)-3-吡啶甲酰胺、3,4,5-三氯-2,6-吡啶二腈、actinovate、顺-1-(4-氯苯基)-2-(1H-1,2,4-三唑-1-基)环庚醇、1-(2,3-二氢-2,2-二甲基-1H-茚-1-基)-1H-咪唑-5-羧酸甲酯、碳酸氢钾、N-(6-甲氧基-3-吡啶基)环丙烷甲酰胺、N-丁基-8-(1,1-二甲基乙基)-1-氧杂螺[4.5]癸烷-3-胺、四硫代碳酸钠;
以及铜盐及其制剂,例如波尔多液、氢氧化铜、环烷酸铜、氯氧化铜(copper oxychloride)、硫酸铜、硫杂灵(cufraneb)、氧化铜、代森锰铜(mancopper)、喹啉铜(oxine-copper)。
杀细菌剂:
溴硝丙二醇(bronopol)、双氯酚、三氯甲基吡啶(nitrapyrin)、二甲基二硫代氨基甲酸镍(nickel dimethyldithiocarbamate)、春雷霉素、异噻菌酮(octhilinone)、羧酸呋喃(furancarboxylic acid)、土霉素(oxytetracyclin)、噻菌灵、链霉素(streptomycin)、叶枯酞、硫酸铜和其他铜制剂。
杀昆虫剂/杀螨剂/杀线虫剂:
1.乙酰胆碱酯酶(AChE)抑制剂
1.1氨基甲酸酯类(例如,棉铃威(alanycarb)、涕灭威(aldicarb)、砜灭威(aldoxycarb)、除害威(allyxycarb)、灭害威(aminocarb)、甲基吡恶磷(azamethiphos)、噁虫威(bendiocarb)、丙硫克百威(benfuracarb)、必克虱(bufencarb)、畜虫威(butacarb)、丁叉威(butocarboxim)、氧丁叉威(butoxycarboxim)、西维因(carbaryl)、虫螨威(carbofuran)、丁硫克百威(carbosulfan)、除线威(choethocarb)、蝇毒磷(coumaphos)、苯腈磷(cyanofenphos)、杀螟腈(cyanophos)、敌蝇威(dimetilan)、苯虫威(ethiofencarb)、丁苯威(fenobucarb)、苯硫威(fenothiocarb)、伐虫脒(formetanate)、呋线威(furathiocarb)、异丙威(isoprocarb)、威百亩(metam-sodium)、灭虫威(methiocarb)、灭多虫(methomyl)、速灭威(metolcarb)、甲氨叉威(oxamyl)、抗蚜威(pirimicarb)、猛杀威(promecarb)、残杀威(propoxur)、硫双灭多威(thiodicarb)、特氨叉威(thiofanox)、唑蚜威(triazamate)、混杀威(trimethacarb)、XMC、灭杀威(xylylcarb))
1.2有机磷酸酯类(例如,高灭磷(acephate)、唑啶磷(azamethiphos)、谷硫磷(azinphos-methyl)、乙基谷硫磷(azinphos-ethyl)、乙基溴硫磷(bromophos-ethy1)、溴苯烯磷(bromfenvinfod(-methyl))、特嘧硫磷(butathiofos)、硫线磷(cadusafos)、三硫磷(carbophenothion)、壤虫氯磷(chlorethoxyfos)、毒虫畏(chlorfenvinphos)、氯甲磷(chlormephos)、甲基毒死蜱(chlorpyrifos-methyl)、乙基毒死蜱、蝇毒磷(coumaphos)、苯腈磷(cyanofenphos)、杀螟腈(cyanophos)、毒虫畏(chlorfenvinphos)、甲基一○五九(demeton-S-methyl)、磺吸磷(demeton-S-methylsulfone)、氯亚磷(dialifos)、二嗪农(diazinon)、除线磷(dichlofenthion)、敌敌畏(dichlorvos)/DDVP、百治磷(dicrotophos)、乐果(dimethoate)、甲基毒虫畏(dimethylvinphos)、蔬果磷(dioxabenzofos)、乙拌磷(disulfoton)、EPN、乙硫磷(ethion)、灭克磷(ethoprophos)、氧嘧啶磷(etrimfos)、氨磺磷(famphur)、克线磷(fenamiphos)、杀螟松(fenitrothion)、丰索磷(fensulfothion)、倍硫磷(fenthion)、吡氟硫磷(flupyrazofos)、地虫磷(fonofos)、安果(formothion)、丁苯硫磷(fosmethilan)、噻唑酮磷(fosthiazate)、庚虫磷(heptenophos)、碘硫磷(iodofenphos)、异稻瘟净(iprobenfos)、氟唑磷(isazofos)、丙胺磷(isofenphos)、O-水杨酸异丙酯、异噁唑啉(isoxathion)、马拉松(malathion)、灭蚜磷(mecarbam)、虫螨畏(methacrifos)、甲胺磷(methamidophos)、杀扑磷(methidathion)、速灭磷(mevinphos)、久效磷(monocrotophos)、二溴磷(naled)、氧化乐果(omethoate)、砜吸磷(oxydemeton-methyl)、甲基一六○五(parathion methyl)、一六○五(-乙基)、稻丰散(phenthoate)、三九一一(phorate)、伏杀磷(phosalone)、亚胺硫磷(phosmet)、磷胺(phosphamidon)、乙丙磷威(phosphocarb)、腈肟磷(phoxim)、虫螨磷(pirimiphos methyl)、乙基虫螨磷(pirimiphos ethyl)、丙溴磷(profenofos)、丙虫磷(propaphos)、烯虫磷(propetamphos)、丙硫磷(prothiofos)、发果(prothoate)、吡唑硫磷(pyraclofos)、打杀磷(pyridaphenthion)、pyridathion、喹噁磷(quinalphos)、硫线磷(sebufos)、硫特普(sulfotep)、乙丙硫磷(sulprofos)、嘧丙磷(tebupirimphos)、双硫磷(temephos)、特丁磷(terbufos)、杀虫畏(tetrachlorvinphos)、甲基乙拌磷(thiometon)、三唑磷(triazophos)、敌百虫(trichlorfon)、蚜灭多(vamidothion))
2.钠通道抑扬调节剂/电压依赖性钠通道阻断剂
2.1合成除虫菊酯类(例如,氟酯菊酯(acrinathrin)、丙烯除虫菊(d-顺-反,d-反)(allethrin(d-cis-trans,d-trans))、β-氟氯氰菊酯(beta-cyfluthrin)、氟氯菊酯(bifenthrin)、反丙烯除虫菊(bioallethrin)、反丙烯除虫菊-S-环戊基异构体、bioethanomethrin、生物氯菊酯(biopermethrin)、右旋反灭虫菊酯(bioresmethrin)、chlovaporthrin、顺-氯氰菊酯、顺-灭虫菊(cis-resmethrin)、顺-氯菊酯(cis-permethrin)、功夫菊酯(clocythrin)、乙氰菊酯(cycloprothrin)、氟氯氰菊酯(cyfluthrin)、氯氟氰菊酯(cyhalothrin)、氯氰菊酯(α-、β-、θ-、ζ-)(cypermethrin(alpha-,beta-,theta-,zeta-))、苯醚氯菊酯(cyphenothrin)、DDT、溴氰菊酯(deltamethrin)、烯炔菊酯(1R异构体)(empenthrin(1R isomer))、高氰戊菊酯(esfenvalerate)、醚菊酯(etofenprox)、五氟苯菊酯(fenfluthrin)、甲氰菊酯(fenpropathrin)、吡氯氰菊酯(fenpyrithrin)、灭杀菊酯(fenvalerate)、溴氟菊酯(flubrocythrinate)、氟氰戊菊酯(flucythrinate)、氟丙苄醚(flufenprox)、氟氯苯菊酯(flumethrin)、氟胺氰菊酯(fluvalinate)、fubfenprox、γ-氯氟氰菊酯(gamma-cyhalothrin)、炔咪菊酯(imiprothrin)、噻嗯菊酯(kadethrin)、λ-氯氟氰菊酯(lambda-cyhalothrin)、甲氧苄氟菊酯(metofluthrin)、氯菊酯(顺-、反-)、苯醚菊酯(1R反式异构体)(phenothrin(1Rtransisomer)、炔酮菊酯(prallethrin)、丙氟菊酯(profluthrin)、protrifenbute、反灭虫菊(pyresmethrin)、灭虫菊、RU-15525、灭虫硅醚(silafluofen)、氟胺氰菊酯(tau-fluvalinate)、七氟菊酯(tefluthrin)、环戊烯丙菊酯(terallethrin)、胺菊酯(1R反式异构体)(tetramethrin(1Rtrans-isomer))、四溴菊酯(tralomethrin)、四氟菊酯(transfluthrin)、ZXI 8901、除虫菊素(pyrethrin)(除虫菊(pyrethrum)))
2.2噁二嗪类(oxadiazine)(例如噁二唑虫(indoxacarb))
3.乙酰胆碱受体激动剂/拮抗剂
3.1氯烟碱基类(chloronicotinyls)/新类烟碱(neonicotinoids)(例如,吡虫清(acetamiprid)、噻虫胺(clothianidin)、呋虫胺(dinotefuran)、吡虫啉、硝胺烯啶(nitenpyram)、硝虫噻嗪(nithiazine)、噻虫啉(thiacloprid)、噻虫嗪(thiamethoxam))
3.2烟碱(nicotine)、杀虫磺(bensultap)、巴丹(cartap)
4.乙酰胆碱受体抑扬调节剂
4.1spinosyn类(例如艾克敌105(spinosad))
5.GABA受控氯通道拮抗剂
5.1环戊二烯有机氯类(例如,毒杀芬(camphechlor)、氯丹(chlordane)、硫丹(endosulfan)、林丹(gamma-HCH)、HCH、七氯(heptachlor)、林丹(lindane)、甲氧滴滴涕(methoxychlor))
5.2fiprole类(例如,乙酞虫睛(acetoprole)、乙虫清(ethiprole)、锐劲特(fipronil)、氟吡唑虫(vaniliprole))
6.氯通道激活剂类
6.1Mectin类(例如,阿维菌素(abamectin,avermectin)、埃玛菌素(emamectin)、埃玛菌素苯甲酸盐(emamectin-benzoate)、伊维菌素(ivermectin)、弥拜菌素(milbemectin)、米尔倍霉素(milbemycin))
7.保幼激素mimetic类(例如,噁茂醚(diofenolan)、epofenonane、双氧威(fenoxycarb)、蒙五一二(hydroprene)、蒙七七七(kinoprene)、蒙五一五(methoprene)、蚊蝇醚(pyriproxifen)、烯虫硫酯(triprene))
8.蜕皮激素激动剂/干扰剂类(disruptor)
8.1二酰基肼类(例如,环虫酰肼(chromafenozide)、特丁苯酰肼(halofenozide)、甲氧苯酰肼(methoxyfenozide)、双苯酰肼(tebufenozide))
9.甲壳质生物合成抑制剂
9.1苯甲酰脲类(例如,双三氟虫脲(bistrifluron)、定虫隆(chlorfluazuron)、氟脲杀(diflubenzuron)、氟啶蜱脲(fluazuron)、氟螨脲(flucycloxuron)、氟虫脲(flufenoxuron)、氟铃脲(hexaflumuron)、氟丙氧脲(lufenuron)、双苯氟脲(novaluron)、多氟脲(noviflumuron)、氟幼脲(penfluron)、伏虫磷(teflubenzuron)、杀虫隆(triflumuron))
9.2噻嗪酮(buprofezin)
9.3灭蝇胺(cyromazine)
10.氧化性磷酸化抑制剂,ATP干扰剂类
10.1杀螨硫隆(diafenthiuron)
10.2有机锡类(例如唑环锡(azocyclotin)、三环锡(cyhexatin)、杀螨锡(fenbutatin-oxide))
11.通过打断H-质子梯度而起作用的氧化性磷酸化去偶剂(decoupler)类
11.1吡咯类(例如氟唑虫清(chlorfenapyr))
11.2二硝基酚类(例如乐杀螨(binapacryl)、敌螨通(dinobuton)、敌螨普(dinocap)、DNOC)
12.侧链-I(Side-I)电子转移抑制剂类
12.1METI类(例如喹螨醚(fenazaquin)、唑螨酯(fenpyroximate)、嘧胺苯醚(pyrimidifen)、哒螨酮(pyridaben)、吡螨胺(tebufenpyrad)、唑虫酰胺(tolfenpyrad))
12.2灭蚁腙(hydramethylnon)
12.3开乐散(dicofol)
13.侧链-II电子转移抑制剂类
13.1鱼藤酮(rotenone)
14.侧链-III电子转移抑制剂类
14.1灭螨醌(acequinocyl)、嘧螨酯(fluacrypyrim)
15.昆虫肠道膜微生物干扰剂类
苏云金杆菌(Bacillus thuringiensis)菌株
16.脂肪合成抑制剂类
16.1季酮酸类(例如,螺螨酯(spirodiclofen)、螺甲螨酯(spiromesifen))
16.2特特拉姆酸类(tetramic acids)(例如,3-(2,5-二甲基苯基)-8-甲氧基-2-氧代-1-氮杂螺[4.5]十二-3-烯-4-基碳酸乙酯(alias:碳酸的3-(2,5-二甲基苯基)-8-甲氧基-2-氧代-1-氮杂螺[4.5]十二-3-烯-4-基乙基酯,CAS Reg.No.:382608-10-8)以及碳酸的顺-3-(2,5-二甲基苯基)-8-甲氧基-2-氧代-1-氮杂螺[4.5]十二-3-烯-4-基乙基酯(CAS Reg.No.:203313-25-1))
17.氨甲酰类(例如氟啶虫酰胺(flonicamid))
18.octopaminergic激动剂类(例如虫螨脒(amitraz))
19.镁激励ATP酶抑制剂类(例如克螨特(propargite))
20.邻苯二酰胺类(例如N2-[1,1-二甲基-2-(甲基磺酰基)乙基]-3-碘-N1-[2-甲基-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]苯基]-1,2-苯二氨甲酰(CAS Reg.No.:272451-65-7)、flubendiamide)
21.沙蚕毒素类似物(例如硫赐安(thiocyclam hydrogenoxalate)、杀虫双(thiosultap-sodium))
22.生物类,激素类或信息素类(例如,艾扎丁(azadirachtin)、杆菌属种、僵菌属种、十二碳二烯醇(codlemone)、绿僵菌属种(Metarrhizium spec.)、拟青霉属种(Paecilomyces spec.)、敌贝特(thuringiensin)、轮枝菌属种(Verticillium spec.))
23.具有未知或未确定作用机理的活性化合物类
23.1熏蒸剂类(例如,磷化铝、一溴甲烷、硫酰氟)
23.2选择性拒食剂类(例如,冰晶石、氟啶虫酰胺(flonicamid)、拒嗪酮(pymetrozine))
23.3螨生长抑制剂类(例如,四螨嗪(clofentezine)、特苯噁唑(etoxazole)、噻螨酮(hexythiazox))
23.4amidoflumet、benclothiaz、苯螨特(benzoximate)、联苯肼酯(bifenazate)、溴螨酯(bromopropylate)、噻嗪酮(buprofezin)、灭螨锰、杀虫脒(chlordimeform)、乙酯杀螨醇(chlorobenzilate)、氯化苦(chloropicrin)、clothiazoben、cycloprene、cyflumetofen、地昔尼尔(dicyclanil)、fenoxacrim、氟硝二苯胺(fentrifanil)、噻唑螨(flubenzimine)、flufenerim、氟替阿嗪(flutenzin)、诱虫十六酯(gossyplure)、灭蚁腙(hydramethylnone)、japonilure、恶虫酮(metoxadiazone)、石油、胡椒基丁醚(piperonyl butoxide)、油酸钾、pyrafluprole、啶虫丙醚(pyridalyl)、pyriprole、氟虫胺(sulfluramid)、三氯杀螨砜(tetradifon)、杀螨好(tetrasul)、苯赛螨(thiarathene)、verbutin,
以及化合物丙基氨基甲酸3-甲基苯基酯(Tsumacide Z)、化合物3-(5-氯-3-吡啶基)-8-(2,2,2-三氟乙基)-8-吖二环[3.2.1]辛烷-3-腈(CAS注册号185982-80-3)以及相应的3-内异构体(CAS注册号185984-60-5)(参见WO 96/37494、WO 98/25923),以及含有杀昆虫性能的活性植物提取物、线虫、真菌或病毒的制剂。
与其它已知化合物—例如除草剂—的混合物,或与肥料以及生长调节剂、安全剂和/或化学信息素的混合物也是可以的。
此外,本发明的式(I)化合物还具有非常好的抗真菌活性。这些化合物具有非常宽的抗真菌作用谱,特别是针对皮肤癣菌(dermatophyte)和酵母菌、霉菌和双相真菌(diphasic fungi)(例如针对念珠菌属(Candida)菌种、例如白色念珠菌(Candida albicans)、光滑念珠菌(Candida glabrata)),以及絮状表面癣菌(Epidermophytonfloccosum),曲霉(Aspergillus)菌种、例如黑曲霉(Aspergillusniger)和烟曲霉(Aspergillus fumigatus),毛癣菌属(Trichophyton)菌种,例如须癣毛癣菌(Trichophyton mentagrophytes),小孢霉属(Microsporon)菌种例如犬小孢霉(Microsporon canis)和Microsporonaudouinii。所列真菌仅为说明目的,而并非限制可涵盖的真菌谱。
本发明的活性化合物可以其本身、其制剂形式或由其制备的使用形式使用,例如即用的溶液剂、悬浮剂、可湿性粉剂、膏剂、可溶性粉剂、粉末剂和颗粒剂。施用以常规方式进行,例如浇灌、喷雾、雾化、撒播(broadcasting)、喷粉、发泡、抛撒等。还可通过超低容量法(ultra-lowvolume method)施用活性化合物,或者将活性化合物制剂或活性化合物本身注射至土壤内。还可处理植物种子。
本发明的活性化合物用作杀真菌剂时,施用率可依据施用类型在较宽的范围内变化。对于植物部位的处理,活性化合物施用率一般为0.1至10000g/ha,优选10至1000g/ha。对于拌种,活性化合物施用率一般为0.001至50g每公斤种子,优选0.01至10g每公斤种子。对于土壤处理,活性化合物施用率一般为0.1至10000g/ha,优选1至5000g/ha。
如上所述,可依据本发明处理所有的植物及其部位。在一个优选实施方案中,处理了野生植物种和植物栽培种,或由常规生物育种方法—例如杂交或原生质体融合—获得的植物种和植物栽培种,以及所述植物种和栽培种的部位。在另一优选实施方案中,处理了由基因工程、如果合适还可与常规方法相结合而获得的转基因植物和植物栽培种(遗传修饰的生物(genetically modified organism))及其部位。术语“部位”或“植物的部位”或“植物部位”解释如上。
特别优选依据本发明进行处理的植物为各自市售或使用的植物栽培种。植物栽培种的含义理解为由常规育种、诱变或重组DNA技术育种的具有新特性(“特征”)的植物。它们可以是栽培种、品种(variety)、生物型(biotype)和基因型形式。
依据植物种或植物栽培种、其种植地点和生长条件(土壤、气候、植物生长期、营养),本发明的处理也可产生超加和性(superadditive)(“协同”)效应。由此,例如,对于可按本发明使用的物质和组合物,可降低其施用率和/或加宽其作用谱和/或提高其活性,以及改善植物生长、提高高温或低温耐受性、提高干旱或水或土壤含盐量耐受性、提高开花品质、使采收更简易、加速成熟、提高产量、改善采收产品的质量和/或提高其营养价值、改善采收产品的贮存稳定性和/或其加工性能,这些可超过实际预期的效果。
优选由本发明处理的转基因植物或植物栽培种(即通过遗传工程获得)包括在重组修饰中接受了遗传物质的所有植物,所述遗传物质将特别有利的有用特性(“特征”)赋予所述植物。所述特性的实例有改善植物生长、提高高温或低温耐受性、提高干旱或水或土壤含盐量耐受性、提高开花品质、使采收更简易、加速成熟、提高产量、改善采收产品的质量和/或提高其营养价值、改善采收产品的贮存稳定性和/或其加工性能。需特别提及的所述特性的其他实例为改善植物对动物和微生物害虫的抵抗力,例如对昆虫、螨虫、植物致病真菌、细菌和/或病毒的抵抗力,以及提高植物对某些除草活性化合物的耐受性。可列举的转基因植物的实例为重要的作物植物,例如谷物(小麦、稻)、玉米、大豆、马铃薯、棉花、烟草、油菜和果树(苹果、梨、柑橘类水果以及葡萄),特别强调的为玉米、大豆、马铃薯、棉花、烟草和油菜。特别强调的特征为通过在植物体内形成毒素,特别是由苏云金杆菌的遗传物质(例如基因CryIA(a)、CryIA(b)、CryIA(c)、CryIIA、CryIIIA、CryIIIB2、Cry9c Cry2Ab、Cry3Bb和CryIF及其结合)在植物体内形成的毒素,来提高植物对昆虫、蛛形纲动物、线虫和蜗牛(slugs and snails)的抵抗力(以下简称为“Bt植物”)。特别强调的其他特征为通过系统获得性抗性(SAR)、系统素、植物抗毒素、引发物和抗性基因以及相应的表达蛋白质和毒素来提高植物对真菌、细菌和病毒的抵抗力。尤其强调的特性为提高植物对某些除草活性化合物的耐受性,例如咪唑啉酮类、磺酰脲类、草甘磷(glyphosate)或phosphinotricin(例如“PAT”基因)。赋予所需要特征的基因也可各自在转基因植物体内相互结合。可列举的“Bt植物”的实例有市售的商标名称为YIELD GARD(例如玉米、棉花、大豆)、KnockOut(例如玉米)、StarLink(例如玉米)、Bollgard(棉花)、Nucotn(棉花)和NewLeaf(马铃薯)的玉米品种、棉花品种、大豆品种和马铃薯品种。可列举的具有除草剂耐受性的植物的实例有市售的商标名称为Roundup Ready(具有草甘磷耐受性,例如玉米、棉花、大豆)、Liberty Link(具有phosphinotricin耐受性,例如油菜)、IMI(具有咪唑啉酮耐受性)和STS(具有磺酰脲耐受性,例如玉米)的玉米品种、棉花品种和大豆品种。可列举的具有除草剂抗性的植物(以常规的除草剂耐受性方式育种的植物)还包括名称为Clearfield的市售品种(例如玉米)。当然,以上叙述也适用于具有所述的或待开发的基因特征的植物栽培种,所述植物栽培种将在未来进行开发和/或上市。
特别有利地,所列出的植物可依据本发明用本发明的通式(I)化合物或活性化合物混合物进行处理。上述活性化合物或混合物的优选范围也适用于所述植物的处理。特别强调的为用本发明特别提及的化合物或混合物对植物进行处理。
本发明的式(I)的化合物还适于抑制人类及哺乳动物中癌细胞的生长。这是基于本发明的化合物与管蛋白(tubulin)以及微管蛋白(microtubuli)相互作用,并促进微管蛋白的聚合而实现的。
为此目的,可以将有效量的式(I)的一种或多种化合物或其可药用盐进行给药。
本发明活性化合物的制备方法和应用由以下实施例阐述。
制备实施例
实施例1
方法(a,变化形式α)
0℃下,将5ml的稀硫酸以及0.4g(0.985mmol)的3-氰基-5-氯-6-(2-氯-6-氟苯基)-7-(3,3-二甲基丁-2-基氨基)吡唑并[1,5-a]嘧啶混合,然后在室温下再搅拌5小时。之后将反应混合物倒在冰上。将得到的沉淀通过抽滤滤出,用水洗涤并干燥。得到0.32g(理论值的61.28%)的3-酰氨基-5-氯-6-(2-氯-6-氟苯基)-7-(3,3-二甲基丁-2-基氨基)吡唑并[1,5-a]嘧啶。
HPLC:logP=3.62
实施例2
方法(a,变化形式β)
室温下,将0.082g(1.181mmol)的羟基氯化铵以及0.800g的Amberlyst A-21添加到0.400g(0.985mmol)的3-氰基-5-氯-6-(2-氯-4-氟苯基)-7-(3,3-二甲基丁-2-基氨基)吡唑并[1,5-a]嘧啶和20ml乙醇的混合物中,并将混合物在室温下振荡16小时。然后再将另外的40mg羟基氯化铵以及200mg的Amberlyst A-21添加到反应混合物中,并将混合物在室温下振荡48小时。按以下所述进行后处理:抽滤得到生成的的固体产物,减压浓缩母液,并使用4∶1的石油醚∶甲基叔丁基醚对残留在硅胶上的剩余物进行色谱分离。得到0.16g(理论值的36.47%)的所述3-肟酰氨基-5-氯-6-(2-氯-4-氟苯基)-7-(3,3-二甲基丁-2-基氨基)吡唑并[1,5-a]嘧啶。
HPLC:logP=2.55
实施例3
方法(a,变化形式γ)
室温下,将于甲醇中的0.053g(0.246mmol)甲醇钠添加到1.000g(2.461mmol)的3-氰基-5-氯-6-(2-氯-4-氟苯基)-7-(3,3-二甲基-丁-2-基氨基)吡唑并[1,5-a]嘧啶和5ml的甲醇的混合物中,并在室温下搅拌混合物48小时。然后添加0.132g(2.461mmol)的氯化铵,并将混合物在室温下搅拌24小时。然后减压浓缩反应混合物。得到0.95g的产物,所述产物含有8.6%的、阻转异构体A形式的所述3-亚氨基酰胺-5-氯-6-(2-氯-4-氟苯基)-7-(3,3-二甲基丁-2-基氨基)吡唑并[1,5-a]嘧啶。
HPLC:logP=2.72
实施例4
方法(a,变化形式γ)
室温下,将于甲醇中的0.053g(0.246mmol)甲醇钠添加到1.0g(2.461mmol)的3-氰基-5-氯-6-(2-氯-4-氟苯基)-7-(3,3-二甲基-丁-2-基氨基)吡唑[1,5-a]嘧啶和25ml的甲醇的混合物中,并在室温下搅拌混合物48小时。然后添加0.132g(2.461mmol)的氯化铵,并将混合物在室温下搅拌24小时。然后减压浓缩反应混合物。得到0.98g的产物,所述产物含有15.24%阻转异构体B形式的3-亚氨基酰胺-5-氯-6-(2-氯-4-氟苯基)-7-(3,3-二甲基丁-2-基氨基)吡唑并[1,5-a]嘧啶。
HPLC:logP=2.58
实施例5
方法(b)
室温,搅拌下,将0.2ml的浓硫酸和0.3ml的水滴加到48mg(0.244mmol)的2,4-二硝基苯肼中。搅拌下,先后添加1ml的乙醇以及0.1g(0.244mmol)3-甲酰基-5-氯-6-(2-氯-4-氟苯基)-7-(3,3-二甲基丁-2-基氨基)吡唑并[1,5-a]嘧啶的10%的溶液。通过抽滤得到生成的固体产物,以水洗涤并干燥。得到0.09g(理论值的56.25%)的3-(2,4-二硝基苯肼亚氨基甲基(2,4-dinitriophenylhydrazimino-methyl))-5-氯-6-(2-氯-4-氟苯基)-7-(3,3-二甲基丁-2-基氨基)吡唑并[1,5-a]嘧啶。
HPLC:logP=6.28
列于表1的下式化合物也可通过上述方法制备。
表1
logP值根据EEC手册79/831附件V.A8(EEC-Directive 79/831Annex V.A8)通过HPLC确定(梯度法,乙腈/0.1%磷酸水溶液)。
原料的制备
实施例36
室温,搅拌下将7.407g(73.194mmol)的2-氨基-3,3-二甲基丁烷添加到在250ml乙腈中的10.0g(29.27mmol)的3-氰基-5,7-二氯-6-(2-氯-6-氟苯基)吡唑并[1,5-a]嘧啶混合物中。添加结束后,将反应混合物在室温下搅拌3小时,然后搅拌添加到水和盐酸的混合物中。通过抽滤得到生成的固体产物,反复水洗并干燥。得到10.8g(理论值的90.97%)的3-氰基-5-氯-6-(2-氯-6-氟苯基)-7-(3,3-二甲基丁-2-基氨基)吡唑并[1,5-a]嘧啶。
HPLC:logP=4.59
实施例37
上式化合物通过实施例18中的方法制备。
HPLC:logP=4.78
实施例38
将48g(0.184mol)的2-氯-4-氟苯基丙二酸二甲酯与19.91g(0.184mol)的4-氰基-5-氨基吡唑以及37.55g(0.203mol)的三正丁胺混合,并将混合物在180℃下搅拌6小时。将反应期间形成的甲醇连续蒸除。然后将反应混合物冷却至室温。95℃、1mbar下,蒸除挥发性组分。得到的剩余物为粗产物形式的6-(2-氯-4-氟苯基)-5,7-二羟基吡唑并[1,5-a]嘧啶-3-腈,该粗产物不需进一步纯化即可用于下一步合成。
实施例39
上式的化合物根据实施例22所述方法制备。
HPLC:logP=0.19
实施例40
将根据实施例22制备的6-(2-氯-4-氟苯基)-5,7-二羟基吡唑并[1,5-a]嘧啶-3-腈粗产物溶于367.3g(2.395mol)的磷酰氯中。室温下,将31.95g(0.153mol)的五氯化磷每次少量地加入。然后使混合物在回馏下沸腾12小时。减压蒸除挥发性组分,将二氯甲烷添加至剩余物中,并以水洗涤混合物。用硫酸钠干燥有机相并减压浓缩。采用3份环己烷和1份乙酸乙酯作为流动相在硅胶上对剩余物进行色谱分离。得到21g、纯度95.7%的3-氰基-5,7-二氯-6-(2-氯-4-氟苯基)吡唑并[1,5-a]嘧啶。
HPLC:logP=3.49
1H-NMR(DMSO-d6,四甲基硅烷):6=7.44-7.52(1H);7.62-7.66(1H);7.71-7.77(1H);9.03(1H)ppm。
实施例41
上式化合物根据实施例24中所述的方法制备。
HPLC:logP=3.31
应用实施例
实施例A
苹果黑星病菌测试(苹果)/保护
溶剂: 24.5重量份的丙酮
24.5重量份的二甲基乙酰胺
乳化剂: 1.0重量份的烷基芳基聚乙二醇醚
为了制备合适的活性化合物制剂,将1重量份的活性化合物与上述用量的溶剂及乳化剂混合,并将浓液以水稀释至所需浓度。
为了测试保护活性,以所述施用率将活性化合物制剂喷洒至幼小植株上。喷洒层干燥后,将苹果霉菌病原体苹果黑星病菌(Venturiainaequalis)的含水分生孢子悬浮液接种于该植株上,然后在约20℃、大气相对湿度100%的培养室继续放置一天。
然后将该植株放置到约21℃、大气相对湿度约90%的温室中。
接种后10天进行评估。0%表示相当于对照样的药效,100%药效表示未观察到侵染。
在本测试中,列于实施例1、2、7、12及13中的本发明化合物在施用率100g/ha下表现出高于90%的药效。
实施例B
灰葡萄孢试验(豆(bean))/保护
溶剂: 24.5重量份丙酮
24.5重量份二甲基乙酰胺
乳化剂: 1重量份烷基芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1重量份的活性化合物与所述量的溶剂和乳化剂混合,将浓液用水稀释至所需浓度。
为测试保护活性,以所述施用率将活性化合物制剂喷洒至幼小植株上。喷洒涂层干燥后,将2小片植入灰葡萄孢(Botrytis cinerea)的琼脂放置在每片叶子上。将接种后的植株放入约20℃、100%相对大气湿度的暗室中。
接种2天后评测叶子上受侵染面积的大小。0%表示药效与对照样相当,100%药效表示未观察到侵染。
在本测试中,列于实施例1、2、7、12及13中的本发明化合物在施用率500g/ha下表现出高于90%的药效。
实施例C
单囊壳白粉病菌试验(黄瓜)/保护
溶剂: 49重量份的N,N-二甲基甲酰胺
乳化剂: 1重量份的烷基芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1重量份的活性化合物与所述量的溶剂和乳化剂混合,将浓液用水稀释至所需浓度。
为测试保护活性,以所述施用率将活性化合物制剂喷洒至幼小黄瓜植株上。处理1天后,将所述植株用单囊壳白粉病菌(Sphaerothecafuliginea)的孢子悬浮液接种。然后将植株放入相对大气湿度70%、温度23℃的温室中。
培养7天后进行评测。0%表示药效与对照样相当,100%药效表示未观察到侵染。
在本测试中,列于实施例2及7中的本发明化合物在施用率750g/ha下表现出高于90%的药效。
Claims (10)
1.下式的吡唑并嘧啶,
其中,
R1代表氢、任选被取代的烷基、任选被取代的链烯基、任选被取代的炔基、任选被取代的环烷基,或代表任选被取代的杂环基,
R2代表氢或烷基,或者,
R1和R2和与其连接的氮原子一起代表任选被取代的杂环,
R3代表氢、卤素、任选被取代的烷基或任选被取代的环烷基,
R4代表
基团,其中
X代表氧原子、HN基团、HO-N基团或Z-O-N=,其中
Z代表任选被取代的烷基或芳基烷基,
或者
R4代表
R7代表氢或烷基,并且
R8代表任选被取代的烷基、任选被取代的苯基,或代表任选被取代的苯基氨基,
R5代表卤素、任选被取代的烷硫基、任选被取代的烷基亚磺酰基,或代表任选被取代的烷基磺酰基,
R6代表任选被取代的芳基。
2.权利要求1的式(I)的吡唑并嘧啶,其中,
R1代表氢、具有1至6个碳原子的烷基,所述烷基可被相同或不同的选自卤素、氰基、羟基、具有1至4个碳原子的烷氧基以及具有3至6个碳原子的环烷基的取代基一取代至五取代,
R1代表具有2至6个碳原子的链烯基,所述链烯基可被相同或不同的选自卤素、氰基、羟基、具有1至4个碳原子的烷氧基以及具有3至6个碳原子的环烷基的取代基一取代至三取代,或者
R1代表具有3至6个碳原子的炔基,所述炔基可被相同或不同的选自卤素、氰基、具有1至4个碳原子的烷氧基以及具有3至6个碳原子的环烷基的取代基一取代至三取代,或者
R1代表具有3至6个碳原子的环烷基,所述环烷基可被相同或不同的选自卤素和具有1至4个碳原子的烷基的取代基一取代至三取代,或者
R1代表具有5或6个环原子以及1至3个杂原子的饱和或不饱和的杂环基,所述杂原子包括例如氮、氧和/或硫,其中杂环基可被选自卤素、具有1至4个碳原子的烷基、氰基、硝基和/或具有3至6个碳原子的环烷基的取代基一取代或二取代,
R2代表氢或具有1至4个碳原子的烷基,或者
R1和R2和与其相连的氮原子一起代表具有3至6个环原子的饱和或不饱和的杂环,其中所述杂环还可含有作为环原子的氮、氧或硫原子,并且所述杂环最多可被氟、氯、溴、具有1至4个碳原子的烷基和/或具有1至4个碳原子和1至9个氟原子和/或氯原子的卤代烷基三取代,
R3代表氢、氟、氯、溴、碘、具有1至4个碳原子的烷基、具有1至4个碳原子和1至9个卤素原子的卤代烷基,或者代表具有3至6个碳原子的环烷基,
R4代表
基团,其中
X代表氧原子、HN基团或HO-N基团,
或者
R4代表
R7代表氢或具有1至4个碳原子的烷基,并且
R8代表羟基、具有1至4个碳原子的烷基,其中每个烷基基团可被具有1至4个碳原子的烷氧基、在烷基部分具有1至3个碳原子的烷基羰基和/或在烷氧基部分具有1至3个碳原子的烷氧基羰基一取代或二取代,或者
R8代表苯基,所述苯基可被相同或不同的选自具有1至4个碳原子的烷基、具有1至4个碳原子的烷氧基、卤素、硝基以及具有1至4个碳原子和1至5个卤素原子的卤代烷基的取代基一取代至三取代,或者
R8代表苯基氨基,所述苯基氨基可被相同或不同的选自具有1至4个碳原子的烷基、具有1至4个碳原子的烷氧基、卤素、硝基以及具有1至4个碳原子和1至5个卤素原子的卤代烷基的取代基一取代至三取代,
R5代表氟、氯、溴、具有1至4个碳原子的烷氧基、具有1至4个碳原子的烷硫基、具有1至4个碳原子的烷基亚磺酰基或具有1至4个碳原子的烷基磺酰基,并且
R6代表苯基,所述苯基可被相同或不同的选自卤素、氰基、硝基、氨基、羟基、甲酰基、羧基、氨基甲酰基、硫代氨基甲酰基的取代基一取代至四取代;
分别具有1至6个碳原子的、各自为直链或带有支链的烷基、烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基;
分别具有2至6个碳原子的、各自为直链或带有支链的链烯基或烯氧基;
分别具有1至6个碳原子和1至13个相同或不同的卤素原子的、各自为直链或带有支链的卤代烷基、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;
分别具有2至6个碳原子和1至11个相同或不同的卤素原子的、各自为直链或带支链的卤代链烯基或卤代烯氧基;
分别在各自的烷基部分中具有1至6个碳原子的、各自为直链或带支链的烷基氨基、二烷基氨基、烷基羰基、烷基羰基氧基、烷氧基羰基、烷基磺酰基氧基、肟基烷基或烷氧基亚氨基烷基;
具有3至6个碳原子的环烷基,
连接于2-,3-位的1,3-丙烷二基、1,4-丁烷二基、亚甲基二氧基(-O-CH2-O)或1,2-亚乙基二氧基(-O-CH2-CH2-O-),其中所述基团可被相同或不同的选自卤素、具有1至4个碳原子的烷基以及具有1至4个碳原子和1至9个相同或不同的卤素原子的卤代烷基的取代基一取代或多取代。
3.权要求1或2的式(I)的吡唑并嘧啶,其中,
R1代表氢或下式的基团
其中,#标记代表连接点,
R2代表氢、甲基、乙基或丙基,或者
R1和R2和与其连接的氮原子一起代表吡咯烷基、哌啶基、吗啉基、硫代吗啉基、哌嗪基、3,6-二氢-1(2H)-哌啶基或四氢-1(2H)-哒嗪基,其中这些基团可被1至3个氟原子、1至3个甲基和/或三氟甲基取代,
或者
R1和R2和与其连接的氮原子一起代表下式的基团,
其中,
R′代表氢或甲基,
R″代表甲基、乙基、氟、氯或三氟甲基,
m 代表数字0、1、2或3,其中,如果m代表2或3,则R″代表相同或不同的基团,
R代表甲基、乙基、氟、氯或三氟甲基,
并且,
n代表数字0、1、2或3,其中,如果n代表2或3,则代表相同或不同的基团,
R3代表氢、氟、氯、溴、碘、甲基、乙基、异丙基、环丙基、环丁基、环戊基、环己基、三氟甲基、1-三氟甲基-2,2,2-三氟乙基或七氟异丙基,
R4代表
基团,其中
X代表氧原子、硫原子、HN基团或HO-N基团,或者
R4代表
R7代表氢、甲基或乙基,并且
R8代表具有1至2个碳原子的烷基,其中每个烷基基团可被甲氧基、乙氧基、甲基羰基、乙基羰基、甲氧基羰基或乙氧基羰基取代,或者
R8代表苯基,所述苯基可被相同或不同的选自甲基、乙基、甲氧基、乙氧基、氟、氯、溴、硝基以及三氟甲基的取代基一取代至三取代,或者
R8代表苯基氨基,所述苯基氨基可被相同或不同的选自甲基、乙基、甲氧基、乙氧基、氟、氯、溴、硝基以及三氟甲基的取代基一取代至三取代,
R5代表氟、氯、溴、甲氧基、乙氧基、甲硫基、甲基亚磺酰基或甲基磺酰基,并且
R6代表苯基,所述苯基可被相同或不同的选自氟、氯、溴、氰基、硝基、甲酰基、甲基、乙基、正或异丙基、正、异、仲或叔丁基、烯丙基、炔丙基、甲氧基、乙氧基、正或异丙氧基、甲硫基、乙硫基、正或异丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基、乙基磺酰基、烯丙基氧基、炔丙基氧基、三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基、三氟乙氧基、二氟甲硫基、二氟一氯甲硫基、三氟甲硫基、三氟甲基亚磺酰基、三氟甲基磺酰基、三氯乙炔基氧基、三氟乙炔基氧基、氯烯丙基氧基、碘炔丙基氧基、甲氨基、乙氨基、正或异丙氨基、二甲氨基、二乙氨基、乙酰基、丙酰基、乙酰氧基、甲氧基羰基、乙氧基羰基、肟基甲基、肟基乙基、甲氧基亚氨基甲基、乙氧基亚氨基甲基、甲氧基亚氨基乙基、乙氧基亚氨基乙基、环丙基、环丁基、环戊基或环己基的取代基一取代至三取代,
连接于2-,3-位的1,3-丙烷二基、亚甲基二氧基(-O-CH2-O-)或1,2-亚乙基二氧基(-O-CH2-CH2-O-),其中所述基团可被相同或不同的选自氟、氯、甲基、乙基、正丙基、异丙基以及三氟甲基的取代基一取代或多取代。
4.权利要求1至3之一或多个中的式(I)的吡唑并嘧啶,其中,
R5代表氟、氯、溴、甲氧基或甲硫基,并且
R6代表2,4-、2,5-、或2,6-二取代的苯基或2-取代的苯基,或代表2,4,6-三取代的苯基,其中取代基选自:
氟、氯、溴、氰基、硝基、甲酰基、甲基、乙基、正或异丙基、正、异、仲或叔丁基、烯丙基、炔丙基、甲氧基、乙氧基、正或异丙氧基、甲硫基、乙硫基、正或异丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基、乙基磺酰基、烯丙基氧基、炔丙基氧基、三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基、三氟乙氧基、二氟甲硫基、二氟一氯甲硫基、三氟甲硫基、三氟甲基亚磺酰基、三氟甲基磺酰基、三氯乙炔基氧基、三氟乙炔基氧基、氯烯丙基氧基、碘炔丙基氧基、甲氨基、乙氨基、正或异丙氨基、二甲氨基、二乙氨基、乙酰基、丙酰基、乙酰氧基、甲氧基羰基、乙氧基羰基、肟基甲基、肟基乙基、甲氧基亚氨基甲基、乙氧基亚氨基甲基、甲氧基亚氨基乙基、乙氧基亚氨基乙基、环丙基、环丁基、环戊基或环己基,
连接于2-,3-位的1,3-丙烷二基、亚甲基二氧基(-O-CH2-O-)或1,2-亚乙基二氧基(-O-CH2-CH2-O-),其中这些基团可被相同或不同的选自氟、氯、甲基、乙基、正丙基、异丙基以及三氟甲基的取代基一取代或多取代。
5.权利要求1至4之一或多个中的式(I)的吡唑并嘧啶的制备方法,其特征在于,
a)下式的氰基化合物,
其中,
R1、R2、R3、R5和R6的定义如上,
α)如合适,在稀释剂存在下,与酸和水反应,
或者,
β)在稀释剂存在下,并且,如合适,在催化剂存在下,与羟胺或羟铵盐反应,
或者,
γ)在碱存在下,并且在稀释剂存在下,与氯化铵反应,
或者,
b)在稀释剂存在下,以及如合适,在催化剂存在下,
下式III的羰基化合物与下式(IV)的氨基化合物反应,
其中,
R1、R2、R3、R5、R6以及R7的定义如上,
H2N-R8 (IV)
其中,R8的定义如上,
其中,式(IV)的氨基化合物还可以其酸加成盐的形式使用。
6.用于防治不想要的微生物的组合物,其特征在于,所述组合物含有至少一种权利要求1至4之一或多个中的式(I)的吡唑并嘧啶,以及填充剂和/或表面活性剂。
7.权利要求6的组合物,还含有至少一种具有杀真菌性能或杀昆虫性能的活性化合物。
8.权利要求1至4之一或多个中的式(I)的吡唑并嘧啶用于防治不想要的微生物的用途。
9.防治不想要的微生物的方法,其特征在于,将权利要求1至4之一或多个中的式(I)的吡唑并嘧啶施用于不想要的微生物和/或其生境。
10.制备用于防治不想要的微生物的组合物的方法,其特征在于,将权利要求1至4之一或多个中的式(I)的吡唑并嘧啶与填充剂和/或表面活性剂混合。
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US5817663A (en) * | 1996-10-07 | 1998-10-06 | American Cyanamid Company | Pentafluorophenylazolopyrimidines |
NZ335422A (en) * | 1996-11-26 | 2000-10-27 | Zeneca Ltd | 8-azabicyclo[3.2.1]octane-, 8-azabicyclo [3.2.1] oct-6-ene-, 9-azabicyclo[3.3.1]nonane-, 9-aza-3-oxabicyclo[3.3.1]nonane- and 9-aza-3-thiabicyclo[3.3.1]nonane derivatives for use in insecticides |
GB9624611D0 (en) * | 1996-11-26 | 1997-01-15 | Zeneca Ltd | Bicyclic amine compounds |
US6156925A (en) * | 1998-09-25 | 2000-12-05 | American Cyanamid Company | Process for the preparation of halogenated phenylmaloates |
US6552026B2 (en) * | 1999-06-14 | 2003-04-22 | Basf Aktiengesellschaft | 6-phenyl-pyrazolopyrimidines |
JP2001019693A (ja) * | 1999-06-14 | 2001-01-23 | American Cyanamid Co | 殺菌・殺カビ性6−フェニル−ピラゾロピリミジン |
DE10223917A1 (de) * | 2002-05-29 | 2003-12-11 | Bayer Cropscience Ag | Pyrazolopyrimidine |
-
2003
- 2003-12-10 DE DE10357568A patent/DE10357568A1/de not_active Withdrawn
-
2004
- 2004-12-08 CN CNA2004800369542A patent/CN1890246A/zh active Pending
- 2004-12-08 US US10/581,775 patent/US20060276478A1/en not_active Abandoned
- 2004-12-08 AT AT04803610T patent/ATE388953T1/de not_active IP Right Cessation
- 2004-12-08 CA CA002548516A patent/CA2548516A1/en not_active Abandoned
- 2004-12-08 KR KR1020067013506A patent/KR20060126685A/ko not_active Application Discontinuation
- 2004-12-08 BR BRPI0417075-0A patent/BRPI0417075A/pt not_active IP Right Cessation
- 2004-12-08 AU AU2004296970A patent/AU2004296970A1/en not_active Abandoned
- 2004-12-08 DE DE502004006528T patent/DE502004006528D1/de not_active Expired - Fee Related
- 2004-12-08 MX MXPA06006421A patent/MXPA06006421A/es not_active Application Discontinuation
- 2004-12-08 WO PCT/EP2004/013931 patent/WO2005056556A1/de active IP Right Grant
- 2004-12-08 EP EP04803610A patent/EP1694681B1/de not_active Not-in-force
- 2004-12-08 JP JP2006543459A patent/JP2007516247A/ja active Pending
- 2004-12-08 EA EA200601128A patent/EA200601128A1/ru unknown
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2006
- 2006-06-06 IL IL176145A patent/IL176145A0/en unknown
- 2006-06-07 ZA ZA200604654A patent/ZA200604654B/xx unknown
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101967149B (zh) * | 2009-07-28 | 2013-01-16 | 北京师范大学 | 18F取代硝基标记的吡唑并[1,5-a]嘧啶类化合物及制备和应用 |
Also Published As
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MXPA06006421A (es) | 2006-08-23 |
JP2007516247A (ja) | 2007-06-21 |
US20060276478A1 (en) | 2006-12-07 |
KR20060126685A (ko) | 2006-12-08 |
ZA200604654B (en) | 2007-10-31 |
EP1694681A1 (de) | 2006-08-30 |
WO2005056556A1 (de) | 2005-06-23 |
EA200601128A1 (ru) | 2006-10-27 |
EP1694681B1 (de) | 2008-03-12 |
ATE388953T1 (de) | 2008-03-15 |
CA2548516A1 (en) | 2005-06-23 |
AU2004296970A1 (en) | 2005-06-23 |
DE10357568A1 (de) | 2005-07-07 |
CR8443A (es) | 2006-11-07 |
BRPI0417075A (pt) | 2007-03-13 |
DE502004006528D1 (en) | 2008-04-24 |
IL176145A0 (en) | 2006-10-05 |
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