JPS5843974A - ７―アミノ―アゾロ［１，５―ａ］ピリミジン及び該化合物を含有する農園芸用殺菌剤 - Google Patents

７―アミノ―アゾロ［１，５―ａ］ピリミジン及び該化合物を含有する農園芸用殺菌剤

Info

Publication number: JPS5843974A
Authority: JP; Japan
Prior art keywords: group; pyrimidine; amino; atom; substituted
Prior art date: 1981-08-01
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Granted

Application number

JP57132278A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0261955B2 (2

Inventor

カ−ル・アイツケン

クラウス・シヤイプ

ハンス・テオバルト

エルンスト−ハインリヒ・ポマ−

エ−ベルハルト・アマ−マン

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF SE

Original Assignee

BASF SE

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1981-08-01

Filing date

1982-07-30

Publication date

1983-03-14

1982-07-30 Application filed by BASF SE filed Critical BASF SE

1983-03-14 Publication of JPS5843974A publication Critical patent/JPS5843974A/ja

1990-12-21 Publication of JPH0261955B2 publication Critical patent/JPH0261955B2/ja

Status Granted legal-status Critical Current

Links

QTAYIMGPWVBIEN-UHFFFAOYSA-N pyrrolo[1,2-a]pyrimidin-7-amine Chemical compound N1=CC=CN2C=C(N)C=C21 QTAYIMGPWVBIEN-UHFFFAOYSA-N 0.000 title claims abstract description 6
230000000844 anti-bacterial effect Effects 0.000 title description 6
239000003899 bactericide agent Substances 0.000 title 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 20
125000000217 alkyl group Chemical group 0.000 claims abstract description 19
125000003118 aryl group Chemical group 0.000 claims abstract description 19
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 18
125000003545 alkoxy group Chemical group 0.000 claims abstract description 17
239000000417 fungicide Substances 0.000 claims abstract description 14
PQNFLJBBNBOBRQ-UHFFFAOYSA-N benzocyclopentane Natural products C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims abstract description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 7
125000002102 aryl alkyloxo group Chemical group 0.000 claims abstract description 7
125000005110 aryl thio group Chemical group 0.000 claims abstract description 7
125000004104 aryloxy group Chemical group 0.000 claims abstract description 7
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims abstract description 7
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 6
125000004659 aryl alkyl thio group Chemical group 0.000 claims abstract description 6
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
125000002947 alkylene group Chemical group 0.000 claims abstract description 5
229910052736 halogen Inorganic materials 0.000 claims abstract 3
125000005843 halogen group Chemical group 0.000 claims description 17
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 11
230000000855 fungicidal effect Effects 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
230000001954 sterilising effect Effects 0.000 claims 1
238000004659 sterilization and disinfection Methods 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
150000002367 halogens Chemical class 0.000 abstract 2
229910052739 hydrogen Inorganic materials 0.000 abstract 1
239000001257 hydrogen Substances 0.000 abstract 1
150000002431 hydrogen Chemical class 0.000 abstract 1
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 abstract 1
125000000547 substituted alkyl group Chemical group 0.000 abstract 1
239000013543 active substance Substances 0.000 description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
-1 phenyloxy Chemical group 0.000 description 16
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
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150000003839 salts Chemical class 0.000 description 8
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WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical class N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 6
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RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 5
235000012239 silicon dioxide Nutrition 0.000 description 5
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QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
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LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
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LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
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MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
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125000001153 fluoro group Chemical group F* 0.000 description 3
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
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150000002790 naphthalenes Chemical class 0.000 description 3
229920000151 polyglycol Polymers 0.000 description 3
239000010695 polyglycol Substances 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
239000000725 suspension Substances 0.000 description 3
FYTLHYRDGXRYEY-UHFFFAOYSA-N 5-Methyl-3-pyrazolamine Chemical compound CC=1C=C(N)NN=1 FYTLHYRDGXRYEY-UHFFFAOYSA-N 0.000 description 2
239000005995 Aluminium silicate Substances 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
240000008067 Cucumis sativus Species 0.000 description 2
235000010799 Cucumis sativus var sativus Nutrition 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
241001223281 Peronospora Species 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
BTANRVKWQNVYAZ-UHFFFAOYSA-N Sec-butyl alcohol Natural products CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
235000009754 Vitis X bourquina Nutrition 0.000 description 2
235000012333 Vitis X labruscana Nutrition 0.000 description 2
240000006365 Vitis vinifera Species 0.000 description 2
235000014787 Vitis vinifera Nutrition 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
239000000853 adhesive Substances 0.000 description 2
239000003513 alkali Substances 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
238000009835 boiling Methods 0.000 description 2
159000000007 calcium salts Chemical class 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
150000001733 carboxylic acid esters Chemical class 0.000 description 2
235000013339 cereals Nutrition 0.000 description 2
239000004927 clay Substances 0.000 description 2
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239000012895 dilution Substances 0.000 description 2
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XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
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GOQYKNQRPGWPLP-UHFFFAOYSA-N heptadecan-1-ol Chemical class CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
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125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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150000003230 pyrimidines Chemical class 0.000 description 2
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VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
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OZOMQRBLCMDCEG-VIZOYTHASA-N 1-[(e)-[5-(4-nitrophenyl)furan-2-yl]methylideneamino]imidazolidine-2,4-dione Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(O1)=CC=C1\C=N\N1C(=O)NC(=O)C1 OZOMQRBLCMDCEG-VIZOYTHASA-N 0.000 description 1
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YIKWKLYQRFRGPM-UHFFFAOYSA-N 1-dodecylguanidine acetate Chemical compound CC(O)=O.CCCCCCCCCCCCN=C(N)N YIKWKLYQRFRGPM-UHFFFAOYSA-N 0.000 description 1
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UKUVVAMSXXBMRX-UHFFFAOYSA-N 2,4,5-trithia-1,3-diarsabicyclo[1.1.1]pentane Chemical compound S1[As]2S[As]1S2 UKUVVAMSXXBMRX-UHFFFAOYSA-N 0.000 description 1
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FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
244000061176 Nicotiana tabacum Species 0.000 description 1
235000002637 Nicotiana tabacum Nutrition 0.000 description 1
239000005662 Paraffin oil Substances 0.000 description 1
241000233614 Phytophthora Species 0.000 description 1
241001149949 Phytophthora cactorum Species 0.000 description 1
241000233626 Plasmopara Species 0.000 description 1
241001281803 Plasmopara viticola Species 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
239000004721 Polyphenylene oxide Substances 0.000 description 1
241001281802 Pseudoperonospora Species 0.000 description 1
241000342307 Pseudoperonospora humuli Species 0.000 description 1
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240000003768 Solanum lycopersicum Species 0.000 description 1
244000061456 Solanum tuberosum Species 0.000 description 1
235000002595 Solanum tuberosum Nutrition 0.000 description 1
235000011941 Tilia x europaea Nutrition 0.000 description 1
229920001807 Urea-formaldehyde Polymers 0.000 description 1
241000219094 Vitaceae Species 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
238000001720 action spectrum Methods 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
150000005215 alkyl ethers Chemical class 0.000 description 1
150000008051 alkyl sulfates Chemical class 0.000 description 1
150000008052 alkyl sulfonates Chemical class 0.000 description 1
ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
229910000148 ammonium phosphate Inorganic materials 0.000 description 1
235000019289 ammonium phosphates Nutrition 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 1
150000007962 benzene acetonitriles Chemical class 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
NBNTWDUNCHRWMT-UHFFFAOYSA-N bis(4-chlorophenyl)-pyridin-3-ylmethanol Chemical compound C=1C=C(Cl)C=CC=1C(C=1C=NC=CC=1)(O)C1=CC=C(Cl)C=C1 NBNTWDUNCHRWMT-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
PFIADAMVCJPXSF-UHFFFAOYSA-N chloroneb Chemical compound COC1=CC(Cl)=C(OC)C=C1Cl PFIADAMVCJPXSF-UHFFFAOYSA-N 0.000 description 1
239000011280 coal tar Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
229940125773 compound 10 Drugs 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000011161 development Methods 0.000 description 1
MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
CJHXCRMKMMBYJQ-UHFFFAOYSA-N dimethirimol Chemical compound CCCCC1=C(C)NC(N(C)C)=NC1=O CJHXCRMKMMBYJQ-UHFFFAOYSA-N 0.000 description 1
239000012990 dithiocarbamate Substances 0.000 description 1
150000004659 dithiocarbamates Chemical class 0.000 description 1
LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000010459 dolomite Substances 0.000 description 1
229910000514 dolomite Inorganic materials 0.000 description 1
235000013399 edible fruits Nutrition 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
230000002538 fungal effect Effects 0.000 description 1
244000000004 fungal plant pathogen Species 0.000 description 1
238000007429 general method Methods 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
235000021021 grapes Nutrition 0.000 description 1
239000003630 growth substance Substances 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
CKAPSXZOOQJIBF-UHFFFAOYSA-N hexachlorobenzene Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl CKAPSXZOOQJIBF-UHFFFAOYSA-N 0.000 description 1
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical class CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
239000004571 lime Substances 0.000 description 1
239000006028 limestone Substances 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
239000000463 material Substances 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
230000001617 migratory effect Effects 0.000 description 1
238000003801 milling Methods 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000008164 mustard oil Substances 0.000 description 1
NZMAJUHVSZBJHL-UHFFFAOYSA-N n,n-dibutylformamide Chemical compound CCCCN(C=O)CCCC NZMAJUHVSZBJHL-UHFFFAOYSA-N 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
229960003540 oxyquinoline Drugs 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229940044652 phenolsulfonate Drugs 0.000 description 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
229960002447 thiram Drugs 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1
235000020234 walnut Nutrition 0.000 description 1
239000002023 wood Substances 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

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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP57132278A 1981-08-01 1982-07-30 ７―アミノ―アゾロ［１，５―ａ］ピリミジン及び該化合物を含有する農園芸用殺菌剤 Granted JPS5843974A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19813130633 DE3130633A1 (de)	1981-08-01	1981-08-01	7-amino-azolo(1,5-a)pyrimidine und diese enthaltende fungizide
DE3130633.0		1981-08-01

Publications (2)

Publication Number	Publication Date
JPS5843974A true JPS5843974A (ja)	1983-03-14
JPH0261955B2 JPH0261955B2 (2)	1990-12-21

Family

ID=6138442

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP57132278A Granted JPS5843974A (ja)	1981-08-01	1982-07-30	７―アミノ―アゾロ［１，５―ａ］ピリミジン及び該化合物を含有する農園芸用殺菌剤

Country Status (15)

Country	Link
US (1)	US4567263A (2)
EP (1)	EP0071792B1 (2)
JP (1)	JPS5843974A (2)
AT (1)	ATE11539T1 (2)
AU (1)	AU553663B2 (2)
CA (1)	CA1180329A (2)
CS (1)	CS226748B2 (2)
DD (1)	DD202093A5 (2)
DE (2)	DE3130633A1 (2)
DK (1)	DK160020C (2)
GR (1)	GR76193B (2)
HU (1)	HU188325B (2)
IE (1)	IE53269B1 (2)
IL (1)	IL66358A0 (2)
ZA (1)	ZA825498B (2)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS59168081A (ja) *	1983-03-15	1984-09-21	New Japan Chem Co Ltd	ム−ス処理剤
JP2005533070A (ja) *	2002-05-29	2005-11-04	バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト	ピラゾロピリミジン及び有害生物を防除するためのその使用
JP2007506665A (ja) *	2003-06-27	2007-03-22	バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト	ピラゾロピリミジン
JP2007516246A (ja) *	2003-12-10	2007-06-21	バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト	ピラゾロピリミジン類
JP2007516247A (ja) *	2003-12-10	2007-06-21	バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト	ピラゾロピリミジン類
JP2007519662A (ja) *	2004-01-22	2007-07-19	ノバルティスアクチエンゲゼルシャフト	タンパク質キナーゼ依存性疾患の処置に使用するためのピラゾロ［１，５−ａ］ピリミジン−７−イル−アミン誘導体
JP2009502860A (ja) *	2005-07-27	2009-01-29	ビーエーエスエフソシエタス・ヨーロピア	アゾロピリミジニルアミンをベースとする殺菌混合物
JP2009511491A (ja) *	2005-10-06	2009-03-19	シェーリングコーポレイション	プロテインキナーゼインヒビターとしてのピラゾロピリミジン
JP2010516726A (ja) *	2007-01-30	2010-05-20	ビーエーエスエフソシエタス・ヨーロピア	アゾロピリミジニルアミン誘導体及び殺虫剤を主成分とする殺虫性混合物
JP2017501177A (ja) *	2013-12-19	2017-01-12	ノバルティスアーゲー	リーシュマニア症などの寄生虫病を処置するための原生動物のプロテアソーム阻害剤としての［１，２，４］トリアゾロ［１，５−ａ］ピリミジン誘導体

Families Citing this family (109)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3338292A1 (de) *	1983-10-21	1985-05-02	Basf Ag, 6700 Ludwigshafen	7-amino-azolo(1,5-a)-pyrimidine und diese enthaltende fungizide
DE3533050A1 (de) *	1985-09-17	1987-03-26	Basf Ag	7-amino-azolo(1,5-a)pyrimidine, verfahren zu ihrer herstellung und diese enthaltende fungizide, bzw. deren verwendung als fungizide
US5459145A (en) *	1988-01-19	1995-10-17	Pfizer Inc.	Calcium independent camp phosphodiesterase inhibitor antidepressant
FI875724L (fi) *	1986-04-29	1987-12-28	Pfizer	Av kalcium oberoende camp fosfodiesteras-inhibitordepressant.
US5593996A (en) *	1991-12-30	1997-01-14	American Cyanamid Company	Triazolopyrimidine derivatives
TW224044B (2)	1991-12-30	1994-05-21	Shell Internat Res Schappej B V
FR2687676B1 (fr) *	1992-02-24	1994-07-08	Union Pharma Scient Appl	Nouveaux derives de polyazaindenes antagonistes des recepteurs a l'angiotensine ii; leurs procedes de preparation, compositions pharmaceutiques les contenant.
US5395935A (en) *	1992-05-08	1995-03-07	Pfizer Inc.	Endo-bicyclo[2.2.1]heptan-2-ol and derived pharmaceutical agents
TW258648B (2) *	1993-03-04	1995-10-01	Shell Internat Res Schappej Bv
US6060478A (en) *	1996-07-24	2000-05-09	Dupont Pharmaceuticals	Azolo triazines and pyrimidines
US7094782B1 (en)	1996-07-24	2006-08-22	Bristol-Myers Squibb Company	Azolo triazines and pyrimidines
US6191131B1 (en)	1997-07-23	2001-02-20	Dupont Pharmaceuticals Company	Azolo triazines and pyrimidines
US6124289A (en) *	1996-07-24	2000-09-26	Dupont Pharmaceuticals Co.	Azolo triazines and pyrimidines
US6313124B1 (en)	1997-07-23	2001-11-06	Dupont Pharmaceuticals Company	Tetrazine bicyclic compounds
US5817663A (en) *	1996-10-07	1998-10-06	American Cyanamid Company	Pentafluorophenylazolopyrimidines
US6117876A (en)	1997-04-14	2000-09-12	American Cyanamid Company	Fungicidal trifluorophenyl-triazolopyrimidines
TW460476B (en) *	1997-04-14	2001-10-21	American Cyanamid Co	Fungicidal trifluoromethylalkylamino-triazolopyrimidines
TWI252231B (en) *	1997-04-14	2006-04-01	American Cyanamid Co	Fungicidal trifluorophenyl-triazolopyrimidines
US5994360A (en) *	1997-07-14	1999-11-30	American Cyanamid Company	Fungicidal 5-alkyl-triazolopyrimidines
FR2765875B1 (fr) *	1997-07-14	1999-11-19	American Cyanamid Co	5-alkyl-triazolopyrimidines fongicides
EP1359150A3 (en) *	1998-02-11	2003-11-19	Basf Aktiengesellschaft	A process and intermediates for the preparation of fungicidal 7-alkyl-triazolopyrimidines
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1981
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1982
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- 1982-07-15 DE DE8282106335T patent/DE3262143D1/de not_active Expired
- 1982-07-15 AT AT82106335T patent/ATE11539T1/de not_active IP Right Cessation
- 1982-07-15 EP EP82106335A patent/EP0071792B1/de not_active Expired
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- 1982-07-22 CA CA000407815A patent/CA1180329A/en not_active Expired
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- 1982-07-30 IE IE1848/82A patent/IE53269B1/en not_active IP Right Cessation
- 1982-07-30 ZA ZA825498A patent/ZA825498B/xx unknown
- 1982-07-30 HU HU822474A patent/HU188325B/hu not_active IP Right Cessation
- 1982-07-30 DK DK341682A patent/DK160020C/da not_active IP Right Cessation
1984
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JPS59168081A (ja) *	1983-03-15	1984-09-21	New Japan Chem Co Ltd	ム−ス処理剤
JP2005533070A (ja) *	2002-05-29	2005-11-04	バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト	ピラゾロピリミジン及び有害生物を防除するためのその使用
JP2007506665A (ja) *	2003-06-27	2007-03-22	バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト	ピラゾロピリミジン
JP2007516246A (ja) *	2003-12-10	2007-06-21	バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト	ピラゾロピリミジン類
JP2007516247A (ja) *	2003-12-10	2007-06-21	バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト	ピラゾロピリミジン類
JP2007519662A (ja) *	2004-01-22	2007-07-19	ノバルティスアクチエンゲゼルシャフト	タンパク質キナーゼ依存性疾患の処置に使用するためのピラゾロ［１，５−ａ］ピリミジン−７−イル−アミン誘導体
JP2009502860A (ja) *	2005-07-27	2009-01-29	ビーエーエスエフソシエタス・ヨーロピア	アゾロピリミジニルアミンをベースとする殺菌混合物
JP2009511491A (ja) *	2005-10-06	2009-03-19	シェーリングコーポレイション	プロテインキナーゼインヒビターとしてのピラゾロピリミジン
JP2010516726A (ja) *	2007-01-30	2010-05-20	ビーエーエスエフソシエタス・ヨーロピア	アゾロピリミジニルアミン誘導体及び殺虫剤を主成分とする殺虫性混合物
JP2017501177A (ja) *	2013-12-19	2017-01-12	ノバルティスアーゲー	リーシュマニア症などの寄生虫病を処置するための原生動物のプロテアソーム阻害剤としての［１，２，４］トリアゾロ［１，５−ａ］ピリミジン誘導体

Also Published As

Publication number	Publication date
US4567263A (en)	1986-01-28
IE821848L (en)	1983-02-01
DK341682A (da)	1983-02-02
CA1180329A (en)	1985-01-02
GR76193B (2)	1984-08-03
EP0071792B1 (de)	1985-01-30
DD202093A5 (de)	1983-08-31
DK160020B (da)	1991-01-14
EP0071792A3 (en)	1983-04-06
ZA825498B (en)	1983-07-27
ATE11539T1 (de)	1985-02-15
DK160020C (da)	1991-06-03
JPH0261955B2 (2)	1990-12-21
DE3130633A1 (de)	1983-02-17
IE53269B1 (en)	1988-09-28
AU553663B2 (en)	1986-07-24
HU188325B (en)	1986-04-28
AU8665982A (en)	1983-02-10
DE3262143D1 (en)	1985-03-14
IL66358A0 (en)	1982-11-30
EP0071792A2 (de)	1983-02-16
CS226748B2 (en)	1984-04-16

Publication	Publication Date	Title
JPS5843974A (ja)	1983-03-14	７―アミノ―アゾロ［１，５―ａ］ピリミジン及び該化合物を含有する農園芸用殺菌剤
USRE32676E (en)	1988-05-24	7-aminozolo[1,5-a]pyrimidines and fungicides containing these
EP0219756A1 (de)	1987-04-29	Neue Acrylsäureamide
WO2006094994A1 (de)	2006-09-14	Verwendung von 4-aminopyrimidinen zur bekämpfung von schadpilzen, neue 4-aminopyrimidine, verfahren zu ihrer herstellung sowie sie enthaltende mittel
JP2000336080A (ja)	2000-12-05	イソチアゾールカルボキサミド類
JPH03145478A (ja)	1991-06-20	オキサゾールカルボン酸アミドまたはチアゾールカルボン酸アミド
CA1136633A (en)	1982-11-30	Imidazole-copper complex compounds, the manufacture thereof, and fungicides containing them
JPS63174986A (ja)	1988-07-19	置換された１，８−ナフチリジン誘導体及び該化合物を含有する殺菌剤
JPS638383A (ja)	1988-01-14	キノリン誘導体及び該化合物を含有する殺菌剤
EP1718305A1 (en)	2006-11-08	Pyrimidine derivatives and use thereof as agricultural and horticultural fungicides
CA1288096C (en)	1991-08-27	7-aminoazolo[1,5-a] pyrimidines, and fungicides containing these
EP0135838B1 (de)	1990-04-18	3-Phenyl-4-methoxycarbonylpyrazole, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchses
DE3541716A1 (de)	1987-05-27	Neue acrylsaeureamide
US4198423A (en)	1980-04-15	1,3-Bis-(trihalomethylsulfenyl)-imidazoline-2,4-diones
EP0054147B1 (de)	1983-10-12	Isatogenderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide
EP0007588B1 (de)	1981-05-13	Tetrahydro-1,3-oxazine, herbizide Mittel, die Acetanilide als herbizide Wirkstoffe und diese Tetrahydro-1,3-oxazine als antagonistische Mittel enthalten, sowie ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchses
JPS6156166A (ja)	1986-03-20	Ｎ−（アリ−ルプロピル）−アゾリル尿素及び該化合物を含有する殺菌剤
EP0010616B1 (de)	1981-04-29	4-Nitro-2-trichlormethylphenylsulfenamide und diese enthaltende Fungizide, deren Herstellung und Verwendung bei der Bekämpfung von Pilzen
IE51887B1 (en)	1987-04-15	Substituted azolylglycol sulfonates,fungicides containing these compounds,and their preparation
EP0040344B1 (de)	1984-12-05	4-Nitro-2-trichlormethylbenzolsulfensäurederivat, Verfahren zu seiner Herstellung, und dieses enthaltende Fungizide
EP0065189A2 (de)	1982-11-24	Heterocyclische Dihalogenacetamide, Verfahren zu ihrer Herstellung und herbizide Mittel, die Acetanilide als herbizide Wirkstoffe und diese Dihalogenacetamide als antagonistische Mittel enthalten
JP2000095778A (ja)	2000-04-04	ピラゾール誘導体、その製造法及び農園芸用の殺菌剤
DE2540872A1 (de)	1977-03-24	Hydantoin-derivate
JPH0318601B2 (2)	1991-03-13
JPH03227977A (ja)	1991-10-08	５―置換―２，４―ジフェニルピリミジン誘導体、その製造法、それを有効成分とする除草剤およびその製造中間体

JPS5843974A - ７―アミノ―アゾロ［１，５―ａ］ピリミジン及び該化合物を含有する農園芸用殺菌剤 - Google Patents

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