IE53269B1 - 7-aminoazolo(1,5-a)pyrimidines and fungicides containing these compounds - Google Patents

7-aminoazolo(1,5-a)pyrimidines and fungicides containing these compounds

Info

Publication number: IE53269B1
Authority: IE; Ireland
Prior art keywords: aminoazolo; substituted; alkyl; alkoxy; halogen
Prior art date: 1981-08-01

Application number

IE1848/82A

Other languages

English (en)

Other versions

IE821848L (en

Original Assignee

Basf Ag

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

1988-09-28

1982-07-30 Application filed by Basf Ag filed Critical Basf Ag

1983-02-01 Publication of IE821848L publication Critical patent/IE821848L/xx

1988-09-28 Publication of IE53269B1 publication Critical patent/IE53269B1/en

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 12
239000000417 fungicide Substances 0.000 title claims abstract description 11
QTAYIMGPWVBIEN-UHFFFAOYSA-N pyrrolo[1,2-a]pyrimidin-7-amine Chemical class N1=CC=CN2C=C(N)C=C21 QTAYIMGPWVBIEN-UHFFFAOYSA-N 0.000 title abstract description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 15
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
229910052736 halogen Inorganic materials 0.000 claims abstract description 10
150000002367 halogens Chemical class 0.000 claims abstract description 10
125000000217 alkyl group Chemical group 0.000 claims abstract description 9
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
PQNFLJBBNBOBRQ-UHFFFAOYSA-N benzocyclopentane Natural products C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims abstract description 7
239000001257 hydrogen Substances 0.000 claims abstract description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 6
125000003118 aryl group Chemical group 0.000 claims abstract description 6
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims abstract description 5
125000002947 alkylene group Chemical group 0.000 claims abstract description 3
150000002431 hydrogen Chemical class 0.000 claims abstract description 3
-1 phenoxy, phenylthio, benzyl Chemical group 0.000 claims description 24
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 9
230000000855 fungicidal effect Effects 0.000 claims description 9
239000000460 chlorine Substances 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 8
241000233866 Fungi Species 0.000 claims description 5
238000000034 method Methods 0.000 claims description 5
SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical class N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
239000007787 solid Substances 0.000 claims description 4
SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
239000007788 liquid Substances 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
125000003545 alkoxy group Chemical group 0.000 abstract description 8
125000004453 alkoxycarbonyl group Chemical group 0.000 abstract description 2
125000003710 aryl alkyl group Chemical group 0.000 abstract 1
125000004659 aryl alkyl thio group Chemical group 0.000 abstract 1
125000002102 aryl alkyloxo group Chemical group 0.000 abstract 1
125000005110 aryl thio group Chemical group 0.000 abstract 1
125000004104 aryloxy group Chemical group 0.000 abstract 1
125000000753 cycloalkyl group Chemical group 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
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 16
239000004480 active ingredient Substances 0.000 description 15
239000000203 mixture Substances 0.000 description 14
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
239000006185 dispersion Substances 0.000 description 11
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000003921 oil Substances 0.000 description 9
239000000243 solution Substances 0.000 description 9
239000002904 solvent Substances 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
239000002253 acid Substances 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
150000001340 alkali metals Chemical class 0.000 description 4
239000004359 castor oil Substances 0.000 description 4
235000019438 castor oil Nutrition 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
239000013078 crystal Substances 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
239000000839 emulsion Substances 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
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 4
229920000151 polyglycol Polymers 0.000 description 4
239000010695 polyglycol Substances 0.000 description 4
239000000843 powder Substances 0.000 description 4
150000003230 pyrimidines Chemical class 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
159000000000 sodium salts Chemical class 0.000 description 4
239000011701 zinc Substances 0.000 description 4
229910052725 zinc Inorganic materials 0.000 description 4
CDIJOYCNNFLOAX-UHFFFAOYSA-N 4-(trichloromethylsulfanyl)isoindole-1,3-dione Chemical compound ClC(Cl)(Cl)SC1=CC=CC2=C1C(=O)NC2=O CDIJOYCNNFLOAX-UHFFFAOYSA-N 0.000 description 3
241000196324 Embryophyta Species 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
241001281803 Plasmopara viticola Species 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
150000007962 benzene acetonitriles Chemical class 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
239000008187 granular material Substances 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
235000012054 meals Nutrition 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000002480 mineral oil Substances 0.000 description 3
235000010446 mineral oil Nutrition 0.000 description 3
150000002790 naphthalenes Chemical class 0.000 description 3
239000006072 paste Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 description 2
WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 2
FYTLHYRDGXRYEY-UHFFFAOYSA-N 5-Methyl-3-pyrazolamine Chemical compound CC=1C=C(N)NN=1 FYTLHYRDGXRYEY-UHFFFAOYSA-N 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
235000009849 Cucumis 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
244000070406 Malus silvestris Species 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
241000109329 Rosa xanthina Species 0.000 description 2
235000004789 Rosa xanthina Nutrition 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
241000219094 Vitaceae Species 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000001464 adherent effect Effects 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
235000021016 apples Nutrition 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
239000000969 carrier Substances 0.000 description 2
235000013339 cereals Nutrition 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
229940125904 compound 1 Drugs 0.000 description 2
229940125773 compound 10 Drugs 0.000 description 2
229940125898 compound 5 Drugs 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
239000007859 condensation product Substances 0.000 description 2
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
239000012990 dithiocarbamate Substances 0.000 description 2
229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000003337 fertilizer Substances 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
238000009472 formulation Methods 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
235000021021 grapes Nutrition 0.000 description 2
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 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
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 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
239000007921 spray Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
235000013311 vegetables Nutrition 0.000 description 2
239000002699 waste material Substances 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 1
QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 description 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
TUBQDCKAWGHZPF-UHFFFAOYSA-N 1,3-benzothiazol-2-ylsulfanylmethyl thiocyanate Chemical compound C1=CC=C2SC(SCSC#N)=NC2=C1 TUBQDCKAWGHZPF-UHFFFAOYSA-N 0.000 description 1
WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 description 1
RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
FKKAGFLIPSSCHT-UHFFFAOYSA-N 1-dodecoxydodecane;sulfuric acid Chemical compound OS(O)(=O)=O.CCCCCCCCCCCCOCCCCCCCCCCCC FKKAGFLIPSSCHT-UHFFFAOYSA-N 0.000 description 1
YIKWKLYQRFRGPM-UHFFFAOYSA-N 1-dodecylguanidine acetate Chemical compound CC(O)=O.CCCCCCCCCCCCN=C(N)N YIKWKLYQRFRGPM-UHFFFAOYSA-N 0.000 description 1
XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
KBLAMUYRMZPYLS-UHFFFAOYSA-N 2,3-bis(2-methylpropyl)naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(O)(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 KBLAMUYRMZPYLS-UHFFFAOYSA-N 0.000 description 1
YTOPFCCWCSOHFV-UHFFFAOYSA-N 2,6-dimethyl-4-tridecylmorpholine Chemical compound CCCCCCCCCCCCCN1CC(C)OC(C)C1 YTOPFCCWCSOHFV-UHFFFAOYSA-N 0.000 description 1
AHPLVFAAWVRBFQ-UHFFFAOYSA-N 2-(2-formyl-3-phenoxyphenyl)acetonitrile Chemical compound O=CC1=C(CC#N)C=CC=C1OC1=CC=CC=C1 AHPLVFAAWVRBFQ-UHFFFAOYSA-N 0.000 description 1
PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
FDZDYFYRIBRQEQ-UHFFFAOYSA-N 2-(4-tert-butyl-2-formylphenyl)acetonitrile Chemical compound CC(C)(C)C1=CC=C(CC#N)C(C=O)=C1 FDZDYFYRIBRQEQ-UHFFFAOYSA-N 0.000 description 1
NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical class CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 1
PRUSWLVZTHLBEB-UHFFFAOYSA-N 2-[2-formyl-3-(trifluoromethyl)phenyl]acetonitrile Chemical compound FC(F)(F)C1=CC=CC(CC#N)=C1C=O PRUSWLVZTHLBEB-UHFFFAOYSA-N 0.000 description 1
BTANRVKWQNVYAZ-UHFFFAOYSA-N 2-butanol Substances CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical compound CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
OOTHTARUZHONSW-UHFFFAOYSA-N 4-[(2-chlorophenyl)hydrazinylidene]-3-methyl-1,2-oxazol-5-one Chemical compound CC1=NOC(=O)C1=NNC1=CC=CC=C1Cl OOTHTARUZHONSW-UHFFFAOYSA-N 0.000 description 1
QXYAENZAKHMNNH-UHFFFAOYSA-N 4-[2-hydroxy-2-(2-hydroxy-3,5-dimethylcyclohexyl)ethyl]piperidine-2,6-dione Chemical compound C1C(C)CC(C)C(O)C1C(O)CC1CC(=O)NC(=O)C1 QXYAENZAKHMNNH-UHFFFAOYSA-N 0.000 description 1
NBBDALDSFZXHQJ-UHFFFAOYSA-N 7a-methylsulfanyl-4,5-dihydro-3ah-isoindole-1,3-dione Chemical compound C1=CCCC2C(=O)NC(=O)C21SC NBBDALDSFZXHQJ-UHFFFAOYSA-N 0.000 description 1
239000005725 8-Hydroxyquinoline Substances 0.000 description 1
244000291564 Allium cepa Species 0.000 description 1
235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 1
239000004254 Ammonium phosphate Substances 0.000 description 1
235000016068 Berberis vulgaris Nutrition 0.000 description 1
241000335053 Beta vulgaris Species 0.000 description 1
241001480061 Blumeria graminis Species 0.000 description 1
241000233685 Bremia lactucae Species 0.000 description 1
REEFSLKDEDEWAO-UHFFFAOYSA-N Chloraniformethan Chemical compound ClC1=CC=C(NC(NC=O)C(Cl)(Cl)Cl)C=C1Cl REEFSLKDEDEWAO-UHFFFAOYSA-N 0.000 description 1
229940126062 Compound A Drugs 0.000 description 1
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PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
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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 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-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
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
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235000012015 potatoes Nutrition 0.000 description 1
AHIHJODVQGBOND-UHFFFAOYSA-M propan-2-yl carbonate Chemical compound CC(C)OC([O-])=O AHIHJODVQGBOND-UHFFFAOYSA-M 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
150000003254 radicals Chemical class 0.000 description 1
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RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
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239000007858 starting material Substances 0.000 description 1
235000021012 strawberries Nutrition 0.000 description 1
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239000004094 surface-active agent Substances 0.000 description 1
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239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
238000012360 testing method Methods 0.000 description 1
WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 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
238000001665 trituration Methods 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
150000003672 ureas Chemical class 0.000 description 1
238000009736 wetting Methods 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)
Dentistry (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Agronomy & Crop Science (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)

IE1848/82A 1981-08-01 1982-07-30 7-aminoazolo(1,5-a)pyrimidines and fungicides containing these compounds IE53269B1 (en)

Applications Claiming Priority (1)

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

Publications (2)

Publication Number	Publication Date
IE821848L IE821848L (en)	1983-02-01
IE53269B1 true IE53269B1 (en)	1988-09-28

Family

ID=6138442

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IE1848/82A IE53269B1 (en)	1981-08-01	1982-07-30	7-aminoazolo(1,5-a)pyrimidines and fungicides containing these compounds

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)

Families Citing this family (119)

* 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
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
WO1987006576A1 (en) *	1986-04-29	1987-11-05	Pfizer Inc.	Calcium independent camp phosphodiesterase inhibitor antidepressant
US5459145A (en) *	1988-01-19	1995-10-17	Pfizer Inc.	Calcium independent camp phosphodiesterase inhibitor antidepressant
TW224044B (2) *	1991-12-30	1994-05-21	Shell Internat Res Schappej B V
US5593996A (en) *	1991-12-30	1997-01-14	American Cyanamid Company	Triazolopyrimidine derivatives
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.
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1981
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1982
- 1982-07-12 GR GR68730A patent/GR76193B/el unknown
- 1982-07-15 AT AT82106335T patent/ATE11539T1/de not_active IP Right Cessation
- 1982-07-15 DE DE8282106335T patent/DE3262143D1/de not_active Expired
- 1982-07-15 EP EP82106335A patent/EP0071792B1/de not_active Expired
- 1982-07-20 IL IL66358A patent/IL66358A0/xx not_active IP Right Cessation
- 1982-07-22 CA CA000407815A patent/CA1180329A/en not_active Expired
- 1982-07-28 DD DD82242024A patent/DD202093A5/de unknown
- 1982-07-29 CS CS825723A patent/CS226748B2/cs 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
- 1982-07-30 IE IE1848/82A patent/IE53269B1/en not_active IP Right Cessation
- 1982-07-30 JP JP57132278A patent/JPS5843974A/ja active Granted
- 1982-07-30 ZA ZA825498A patent/ZA825498B/xx unknown
- 1982-07-30 AU AU86659/82A patent/AU553663B2/en not_active Ceased
1984
- 1984-09-18 US US06/651,660 patent/US4567263A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
GR76193B (2)	1984-08-03
ZA825498B (en)	1983-07-27
JPH0261955B2 (2)	1990-12-21
ATE11539T1 (de)	1985-02-15
EP0071792A3 (en)	1983-04-06
HU188325B (en)	1986-04-28
EP0071792B1 (de)	1985-01-30
US4567263A (en)	1986-01-28
DE3130633A1 (de)	1983-02-17
DK341682A (da)	1983-02-02
EP0071792A2 (de)	1983-02-16
IE821848L (en)	1983-02-01
DE3262143D1 (en)	1985-03-14
DK160020B (da)	1991-01-14
CA1180329A (en)	1985-01-02
DK160020C (da)	1991-06-03
IL66358A0 (en)	1982-11-30
AU8665982A (en)	1983-02-10
AU553663B2 (en)	1986-07-24
DD202093A5 (de)	1983-08-31
CS226748B2 (en)	1984-04-16
JPS5843974A (ja)	1983-03-14

Legal Events

Date	Code	Title	Description
1997-03-26	MM4A	Patent lapsed

Publication	Publication Date	Title
US4567263A (en)	1986-01-28	7-Aminoazolo[1,5-a]-pyrimidines and fungicides containing these compounds
USRE32676E (en)	1988-05-24	7-aminozolo[1,5-a]pyrimidines and fungicides containing these
US4801592A (en)	1989-01-31	Substituted 1,8-naphthyridine derivatives and fungicides containing them
JP2004531527A (ja)	2004-10-14	殺菌剤としての５−ハロゲン−６−フェニル−７−フルオロアルキルアミノ−トリアゾロピリミジン類
US4430336A (en)	1984-02-07	N-Substituted 2-methylnaphthylamides, their preparation and fungicides containing these compounds
CA1288096C (en)	1991-08-27	7-aminoazolo[1,5-a] pyrimidines, and fungicides containing these
JP2004526767A (ja)	2004-09-02	６−（２−クロロ−６−フルオロ−フェニル）−トリアゾロピリミジン類
JPH0272141A (ja)	1990-03-12	アクリルエステル及び該アクリルエステルを含有する殺菌剤
IL44737A (en)	1977-02-28	5-substituted-3-(3,5-dichlorophenyl)-2,4-oxazolidinedione derivatives and fungicidal compositions containing them
PL123432B1 (2)	1982-10-31
US4521429A (en)	1985-06-04	Vinylazoles and their use for controlling fungi
US4568684A (en)	1986-02-04	N-Substituted 2-methylnaphthylamides, their preparation, and fungicides containing these compounds
PL119823B2 (en)	1982-01-30	Fungicide
JPH01275566A (ja)	1989-11-06	アゾリルメチルアリルアルコール及び該化合物を含有する殺菌剤並びに真菌類の防除法
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