DE3130633A1 - 7-amino-azolo(1,5-a)pyrimidine und diese enthaltende fungizide - Google Patents
7-amino-azolo(1,5-a)pyrimidine und diese enthaltende fungizideInfo
- Publication number
- DE3130633A1 DE3130633A1 DE19813130633 DE3130633A DE3130633A1 DE 3130633 A1 DE3130633 A1 DE 3130633A1 DE 19813130633 DE19813130633 DE 19813130633 DE 3130633 A DE3130633 A DE 3130633A DE 3130633 A1 DE3130633 A1 DE 3130633A1
- Authority
- DE
- Germany
- Prior art keywords
- amino
- substituted
- alkyl
- formula
- parts
- Prior art date
- 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.)
- Withdrawn
Links
- 239000000417 fungicide Substances 0.000 title claims abstract description 13
- 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 abstract description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 12
- 125000003118 aryl group Chemical group 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical class 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 229910052757 nitrogen 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 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 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 4
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims abstract description 4
- 125000005110 aryl thio group Chemical group 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 125000004104 aryloxy group Chemical group 0.000 claims abstract 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract 2
- -1 Alkoxl Chemical group 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 6
- 150000003230 pyrimidines Chemical class 0.000 claims description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical class N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- MUQNGPZZQDCDFT-JNQJZLCISA-N Halcinonide Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CCl)[C@@]1(C)C[C@@H]2O MUQNGPZZQDCDFT-JNQJZLCISA-N 0.000 claims 1
- 229940028332 halog Drugs 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 abstract 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000004480 active ingredient Substances 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 125000001309 chloro group Chemical group Cl* 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
- 239000000203 mixture Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000003513 alkali Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000000460 chlorine Chemical group 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 230000000855 fungicidal effect Effects 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 150000007962 benzene acetonitriles Chemical class 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000004359 castor oil Substances 0.000 description 4
- 235000019438 castor oil Nutrition 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
- 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
- 239000000843 powder Substances 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 238000004519 manufacturing process Methods 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
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000005406 washing Methods 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
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 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
- 235000009849 Cucumis sativus Nutrition 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
- 241001223281 Peronospora Species 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 241000233626 Plasmopara Species 0.000 description 2
- 241001281803 Plasmopara viticola Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229920001807 Urea-formaldehyde Polymers 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 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
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 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
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical class OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 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
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000012362 glacial acetic acid Substances 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
- 229920005610 lignin Polymers 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
- 238000002156 mixing Methods 0.000 description 2
- 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 2
- 239000006072 paste Substances 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
- 238000005507 spraying Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 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
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
- 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
- VPGSXIKVUASQIY-UHFFFAOYSA-N 1,2-dibutylnaphthalene Chemical class C1=CC=CC2=C(CCCC)C(CCCC)=CC=C21 VPGSXIKVUASQIY-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
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-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
- 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
- UPTVJAJPBGIRLZ-UHFFFAOYSA-N 2-(trichloromethylsulfanyl)-3a,4,5,7a-tetrahydroisoindole-1,3-dione Chemical compound C1CC=CC2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C21 UPTVJAJPBGIRLZ-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
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- OQFMDNQUPJYDSH-UHFFFAOYSA-N 2-methyl-5-phenylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=C(N)N2N=C(C)C=C2N=C1C1=CC=CC=C1 OQFMDNQUPJYDSH-UHFFFAOYSA-N 0.000 description 1
- FSCWZHGZWWDELK-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-5-ethenyl-5-methyl-2,4-oxazolidinedione Chemical compound O=C1C(C)(C=C)OC(=O)N1C1=CC(Cl)=CC(Cl)=C1 FSCWZHGZWWDELK-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
- 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 1
- FYTLHYRDGXRYEY-UHFFFAOYSA-N 5-Methyl-3-pyrazolamine Chemical compound CC=1C=C(N)NN=1 FYTLHYRDGXRYEY-UHFFFAOYSA-N 0.000 description 1
- GDXOXXFNKIBVCW-UHFFFAOYSA-N 5-ethoxy-3-(trichloromethyl)-2h-thiadiazole;methyl n-(1h-benzimidazol-2-yl)carbamate Chemical compound CCOC1=CN(C(Cl)(Cl)Cl)NS1.C1=CC=C2NC(NC(=O)OC)=NC2=C1 GDXOXXFNKIBVCW-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 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
- UQZZUHYCKPDOAK-UHFFFAOYSA-N C1(CCCCC1)NC(=O)C1=C(OC(=C1)C)C.CC=1OC=CC1C(=O)NC1=CC=CC=C1.CC=1OC(=C(C1C(=O)NC1=CC=CC=C1)C)C Chemical compound C1(CCCCC1)NC(=O)C1=C(OC(=C1)C)C.CC=1OC=CC1C(=O)NC1=CC=CC=C1.CC=1OC(=C(C1C(=O)NC1=CC=CC=C1)C)C UQZZUHYCKPDOAK-UHFFFAOYSA-N 0.000 description 1
- LFHPXUNMLXTQBA-UHFFFAOYSA-N CC1=C(C(=O)NC2=CC=CC=C2)C=CC=C1.CC=1OC(=CC1C(=O)NC1=CC=CC=C1)C Chemical compound CC1=C(C(=O)NC2=CC=CC=C2)C=CC=C1.CC=1OC(=CC1C(=O)NC1=CC=CC=C1)C LFHPXUNMLXTQBA-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- HDABKDMJAICYSH-UHFFFAOYSA-N ClC1=NC(=NC(=N1)Cl)NC1=C(C=CC=C1)Cl.C(C)(=O)O.C(CCCCCCCCCCCCCCCC)C=1NCCN1 Chemical compound ClC1=NC(=NC(=N1)Cl)NC1=C(C=CC=C1)Cl.C(C)(=O)O.C(CCCCCCCCCCCCCCCC)C=1NCCN1 HDABKDMJAICYSH-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical class OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- HDWLUGYOLUHEMN-UHFFFAOYSA-N Dinobuton Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(=O)OC(C)C HDWLUGYOLUHEMN-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 241000221787 Erysiphe Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 240000009088 Fragaria x ananassa Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000208818 Helianthus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 235000008694 Humulus lupulus Nutrition 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 235000003228 Lactuca sativa Nutrition 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241001149951 Mucor mucedo Species 0.000 description 1
- 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
- FPZKMSBEPGFUEO-UHFFFAOYSA-N N.C(N)(SCCSC(N)=S)=S.[Zn].[Mn].C(N)(SCCSC(N)=S)=S.[Mn] Chemical compound N.C(N)(SCCSC(N)=S)=S.[Zn].[Mn].C(N)(SCCSC(N)=S)=S.[Mn] FPZKMSBEPGFUEO-UHFFFAOYSA-N 0.000 description 1
- 241000498271 Necator Species 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 241001670201 Peronospora destructor Species 0.000 description 1
- 241000233614 Phytophthora Species 0.000 description 1
- 241000233622 Phytophthora infestans Species 0.000 description 1
- 241000233629 Phytophthora parasitica Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 241001281805 Pseudoperonospora cubensis Species 0.000 description 1
- 241000342307 Pseudoperonospora humuli Species 0.000 description 1
- 241000235546 Rhizopus stolonifer Species 0.000 description 1
- 235000004789 Rosa xanthina Nutrition 0.000 description 1
- 241000109329 Rosa xanthina Species 0.000 description 1
- 241001183191 Sclerophthora macrospora Species 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis 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
- 235000011054 acetic acid Nutrition 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 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
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 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
- 239000001166 ammonium sulphate Substances 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
- LJOZMWRYMKECFF-UHFFFAOYSA-N benodanil Chemical compound IC1=CC=CC=C1C(=O)NC1=CC=CC=C1 LJOZMWRYMKECFF-UHFFFAOYSA-N 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
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Inorganic materials [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
- 239000001175 calcium sulphate Substances 0.000 description 1
- 235000011132 calcium sulphate Nutrition 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- GYSSRZJIHXQEHQ-UHFFFAOYSA-N carboxin Chemical compound S1CCOC(C)=C1C(=O)NC1=CC=CC=C1 GYSSRZJIHXQEHQ-UHFFFAOYSA-N 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- PFIADAMVCJPXSF-UHFFFAOYSA-N chloroneb Chemical compound COC1=CC(Cl)=C(OC)C=C1Cl PFIADAMVCJPXSF-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000013066 combination product Substances 0.000 description 1
- 229940127555 combination product Drugs 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940125807 compound 37 Drugs 0.000 description 1
- 229940126540 compound 41 Drugs 0.000 description 1
- 229940125936 compound 42 Drugs 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 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
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- PYZSVQVRHDXQSL-UHFFFAOYSA-N dithianon Chemical compound S1C(C#N)=C(C#N)SC2=C1C(=O)C1=CC=CC=C1C2=O PYZSVQVRHDXQSL-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
- 239000000428 dust Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000001153 fluoro group Chemical group F* 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
- 230000002464 fungitoxic effect Effects 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N heptadecan-1-ol Chemical class CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 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
- 150000004678 hydrides Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 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 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000010807 litter Substances 0.000 description 1
- RENRQMCACQEWFC-UGKGYDQZSA-N lnp023 Chemical compound C1([C@H]2N(CC=3C=4C=CNC=4C(C)=CC=3OC)CC[C@@H](C2)OCC)=CC=C(C(O)=O)C=C1 RENRQMCACQEWFC-UGKGYDQZSA-N 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
- 235000012245 magnesium oxide Nutrition 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
- 235000009973 maize Nutrition 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- NZMAJUHVSZBJHL-UHFFFAOYSA-N n,n-dibutylformamide Chemical compound CCCCN(C=O)CCCC NZMAJUHVSZBJHL-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 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 compound 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
- 230000020477 pH reduction Effects 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229940044654 phenolsulfonic acid 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
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical compound O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 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
- 230000000630 rising effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000005624 silicic acid group Chemical class 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
- 239000007858 starting material Substances 0.000 description 1
- 235000021012 strawberries Nutrition 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
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- ILERPRJWJPJZDN-UHFFFAOYSA-N thioquinox Chemical compound C1=CC=C2N=C(SC(=S)S3)C3=NC2=C1 ILERPRJWJPJZDN-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
- 150000003672 ureas Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 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)
Priority Applications (16)
| 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 |
| GR68730A GR76193B (enExample) | 1981-08-01 | 1982-07-12 | |
| DE8282106335T DE3262143D1 (en) | 1981-08-01 | 1982-07-15 | 7-amino-azolo-(1,5-a)-pyrimidines process for their production and fungicides containing them |
| AT82106335T ATE11539T1 (de) | 1981-08-01 | 1982-07-15 | 7-amino-azolo(1,5-a)pyrimidine, verfahren zu ihrer herstellung und diese enthaltende fungizide. |
| EP82106335A EP0071792B1 (de) | 1981-08-01 | 1982-07-15 | 7-Amino-azolo(1,5-a)pyrimidine, Verfahren zu ihrer Herstellung und diese enthaltende Fungizide |
| IL66358A IL66358A0 (en) | 1981-08-01 | 1982-07-20 | 7-aminoazolo(1,5-a)pyrimidines,their manufacture and their use as fungicides |
| CA000407815A CA1180329A (en) | 1981-08-01 | 1982-07-22 | 7-aminoazolo[1,5-a]pyrimidines and fungicides containing these compounds |
| DD82242024A DD202093A5 (de) | 1981-08-01 | 1982-07-28 | Fungizide mittel |
| CS825723A CS226748B2 (en) | 1981-08-01 | 1982-07-29 | Fungicide |
| HU822474A HU188325B (en) | 1981-08-01 | 1982-07-30 | Fungicides containing 7-amino-azolo/1,5-a/pyrimidines and process for the production of the active substances |
| DK341682A DK160020C (da) | 1981-08-01 | 1982-07-30 | 7-amino-azolooe1,5-aaapyrimidiner og disses anvendelse som fungicider |
| AU86659/82A AU553663B2 (en) | 1981-08-01 | 1982-07-30 | 7-aminoazolo(1,5-alpha)pyrimidines |
| IE1848/82A IE53269B1 (en) | 1981-08-01 | 1982-07-30 | 7-aminoazolo(1,5-a)pyrimidines and fungicides containing these compounds |
| JP57132278A 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 |
| ZA825498A ZA825498B (en) | 1981-08-01 | 1982-07-30 | 7-aminoazolo(1,5-a)pyrimidines and fungicides containing these compounds |
| US06/651,660 US4567263A (en) | 1981-08-01 | 1984-09-18 | 7-Aminoazolo[1,5-a]-pyrimidines and fungicides containing these compounds |
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 (1)
| Publication Number | Publication Date |
|---|---|
| DE3130633A1 true DE3130633A1 (de) | 1983-02-17 |
Family
ID=6138442
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19813130633 Withdrawn DE3130633A1 (de) | 1981-08-01 | 1981-08-01 | 7-amino-azolo(1,5-a)pyrimidine und diese enthaltende fungizide |
| DE8282106335T Expired DE3262143D1 (en) | 1981-08-01 | 1982-07-15 | 7-amino-azolo-(1,5-a)-pyrimidines process for their production and fungicides containing them |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8282106335T Expired DE3262143D1 (en) | 1981-08-01 | 1982-07-15 | 7-amino-azolo-(1,5-a)-pyrimidines process for their production and fungicides containing them |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4567263A (enExample) |
| EP (1) | EP0071792B1 (enExample) |
| JP (1) | JPS5843974A (enExample) |
| AT (1) | ATE11539T1 (enExample) |
| AU (1) | AU553663B2 (enExample) |
| CA (1) | CA1180329A (enExample) |
| CS (1) | CS226748B2 (enExample) |
| DD (1) | DD202093A5 (enExample) |
| DE (2) | DE3130633A1 (enExample) |
| DK (1) | DK160020C (enExample) |
| GR (1) | GR76193B (enExample) |
| HU (1) | HU188325B (enExample) |
| IE (1) | IE53269B1 (enExample) |
| IL (1) | IL66358A0 (enExample) |
| ZA (1) | ZA825498B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004000844A1 (de) * | 2002-05-29 | 2003-12-31 | Bayer Cropscience Aktiengesellschaft | Pyrazolopyrimidine und ihre verwendung zur bekämpfung von schädlichen organismen |
| US7629294B2 (en) | 2004-02-20 | 2009-12-08 | Bayer Cropscience Lp | Pyrazolopyrimidines |
Families Citing this family (117)
| 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 |
| HU215433B (hu) * | 1986-04-29 | 2000-05-28 | Pfizer Inc. | Eljárás új 2-oxo-5-fenil-pirimidin-származékok előállítására |
| US5459145A (en) * | 1988-01-19 | 1995-10-17 | Pfizer Inc. | Calcium independent camp phosphodiesterase inhibitor antidepressant |
| TW224044B (enExample) * | 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. |
| US5395935A (en) * | 1992-05-08 | 1995-03-07 | Pfizer Inc. | Endo-bicyclo[2.2.1]heptan-2-ol and derived pharmaceutical agents |
| IL108731A (en) * | 1993-03-04 | 1997-03-18 | Shell Int Research | 6, N-DISUBSTITUTED-£1, 2, 4| TRIAZOLO-£1, 5-a| PYRIMIDINE- 7-AMINE DERIVATIVES, THEIR PREPARATION AND THEIR USE AS FUNGICIDES |
| US6313124B1 (en) | 1997-07-23 | 2001-11-06 | Dupont Pharmaceuticals Company | Tetrazine bicyclic compounds |
| US6191131B1 (en) | 1997-07-23 | 2001-02-20 | Dupont Pharmaceuticals Company | Azolo triazines and pyrimidines |
| US6060478A (en) * | 1996-07-24 | 2000-05-09 | Dupont Pharmaceuticals | Azolo triazines and pyrimidines |
| US6124289A (en) * | 1996-07-24 | 2000-09-26 | Dupont Pharmaceuticals Co. | Azolo triazines and pyrimidines |
| US7094782B1 (en) | 1996-07-24 | 2006-08-22 | Bristol-Myers Squibb Company | Azolo triazines and pyrimidines |
| US5817663A (en) * | 1996-10-07 | 1998-10-06 | American Cyanamid Company | Pentafluorophenylazolopyrimidines |
| 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 |
| US6117876A (en) * | 1997-04-14 | 2000-09-12 | American Cyanamid Company | 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 |
| PT1054888E (pt) * | 1998-02-11 | 2004-02-27 | Basf Ag | 7-alquil-triazolopirimidinas fungicidas |
| US6020338A (en) * | 1998-02-11 | 2000-02-01 | American Cyanamid Company | Fungicidal 7-alkyl-triazolopyrimidines |
| US6124301A (en) * | 1998-03-17 | 2000-09-26 | American Cyanamid Company | Enhancement of the efficacy of triazolopyrimidines |
| JPH11322517A (ja) * | 1998-03-17 | 1999-11-24 | American Cyanamid Co | トリアゾロピリミジン類の効力の増進 |
| US5981534A (en) * | 1998-09-25 | 1999-11-09 | American Cyanamid Company | Fungicidal 6-(2,6-difluoro-4-alkoxyphenyl)-triazolopyrimidines |
| EA003281B1 (ru) * | 1998-03-23 | 2003-04-24 | Америкэн Цианамид Компани | 6-(2-гало-4-алкоксифенил)триазолпиримидины с фунгицидным действием |
| US6268371B1 (en) | 1998-09-10 | 2001-07-31 | American Cyanamid Co. | Fungicidal mixtures |
| PE20001145A1 (es) * | 1998-09-10 | 2000-10-25 | American Cyanamid Co | Mezclas fungicidas |
| US6117865A (en) * | 1998-09-10 | 2000-09-12 | American Cyanamid Company | Fungicidal trifluorophenyl-triazolopyrimidines |
| JP2000103790A (ja) * | 1998-09-25 | 2000-04-11 | American Cyanamid Co | 殺菌・殺カビ性のトリハロフェニル―トリアゾロピリミジン類 |
| US6277857B1 (en) * | 1998-09-25 | 2001-08-21 | American Cyanamid Company | Fungicidal 7-oxy-and 7-thio-substituted-triazolopyrimidines |
| AU765664B2 (en) * | 1998-09-25 | 2003-09-25 | Basf Aktiengesellschaft | Non-aqueous suspension concentrate |
| US5986135A (en) * | 1998-09-25 | 1999-11-16 | American Cyanamid Company | Fungicidal trifluoromethylalkylamino-triazolopyrimidines |
| FR2784380B1 (fr) * | 1998-09-25 | 2002-09-06 | American Cyanamid Co | Triazolopyrimidines 7-oxy- et 7-thio-substituees fongicides |
| US6242451B1 (en) | 1998-09-25 | 2001-06-05 | Klaus-Juergen Pees | Fungicidal trihalophenyl-triazolopyrimidines |
| US6165940A (en) * | 1998-09-25 | 2000-12-26 | American Cyanamid Co. | Non-aqueous suspension concentrate |
| US5985883A (en) * | 1998-09-25 | 1999-11-16 | American Cyanamid Company | Fungicidal trichlorophenyl-triazolopyrimidines |
| AU4331500A (en) | 1999-04-06 | 2000-10-23 | Du Pont Pharmaceuticals Company | Pyrazolotriazines as crf antagonists |
| WO2000059908A2 (en) | 1999-04-06 | 2000-10-12 | Du Pont Pharmaceuticals Company | Pyrazolopyrimidines as crf antagonists |
| US6552026B2 (en) | 1999-06-14 | 2003-04-22 | Basf Aktiengesellschaft | 6-phenyl-pyrazolopyrimidines |
| FR2795073B1 (fr) * | 1999-06-15 | 2002-08-16 | American Cyanamid Co | 6-(5-fluoro-2-trifluoromethylphenyl)-triazolopyrimidines fongicides |
| WO2001035738A2 (en) | 1999-11-18 | 2001-05-25 | Basf Corporation | Non-aqueous concentrated spreading oil composition |
| US6559151B2 (en) | 2000-05-08 | 2003-05-06 | Basf Aktiengesellschaft | 6-(2-trifluoromethyl-phenyl)-triazolopyrimidines |
| US6630476B2 (en) | 2000-07-07 | 2003-10-07 | Bristol-Myers Squibb Pharma Company | Pyrrolo [3,4-d] pyrimidines as corticotropin releasing factor (CRF) antagonists |
| WO2002046195A1 (en) * | 2000-12-06 | 2002-06-13 | Basf Aktiengesellschaft | Fungicidal 6-(trifluoromethyl-phenyl)-triazolopyrimidines |
| WO2002048151A1 (en) * | 2000-12-11 | 2002-06-20 | Basf Aktiengesellschaft | 6-phenyl-pyrazolopyrimidines |
| DE60104087T2 (de) * | 2001-04-09 | 2004-10-28 | Basf Ag | Fungizide 5-Alkylamino-6-phenyl-7-halogen-Triazolopyrimidine |
| SK12522003A3 (sk) * | 2001-04-11 | 2004-05-04 | Basf Aktiengesellschaft | 5-Halogén-6-fenyl-7-fluóralkylaminotriazolopyrimidíny |
| JP2004526767A (ja) * | 2001-04-11 | 2004-09-02 | ビーエーエスエフ アクチェンゲゼルシャフト | 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 |
| US20030232794A1 (en) * | 2001-06-26 | 2003-12-18 | Cottam Howard B. | Use of STAT-6 inhibitors as therapeutic agents |
| US7601846B2 (en) * | 2001-06-26 | 2009-10-13 | The Regents Of The University Of California | Compounds having activity as inhibitors of apoptosis |
| EA007164B1 (ru) | 2001-07-05 | 2006-08-25 | Басф Акциенгезельшафт | Фунгицидные триазолопиримидины, способ их получения и их применение для борьбы с фитопатогенными грибами, а также содержащие их средства |
| JP2005504744A (ja) * | 2001-07-18 | 2005-02-17 | ビーエーエスエフ アクチェンゲゼルシャフト | 殺菌薬としての置換された６−（２−トリル）−トリアゾロピリミジン |
| NZ531066A (en) * | 2001-07-18 | 2005-04-29 | Basf Ag | 6-(2,6-difluorophenyl)-triazolopyrimidines as fungicides |
| WO2003008416A1 (en) * | 2001-07-18 | 2003-01-30 | Basf Aktiengesellschaft | Substituted 6-(2-methoxyphenyl) triazolopyrimides as fungicides |
| WO2003031587A2 (en) * | 2001-10-09 | 2003-04-17 | The Regents Of The University Of California | Use of stat-6 inhibitors as therapeutic agents |
| GB0126914D0 (en) * | 2001-11-08 | 2002-01-02 | Syngenta Ltd | Fungicides |
| BR0308529A (pt) * | 2002-03-21 | 2005-02-01 | Basf Ag | Compostos, processos para a preparação dos mesmos e para o combate de fungos nocivos, e, agente adequado para o combate de fungos nocivos |
| UA80304C2 (en) | 2002-11-07 | 2007-09-10 | Basf Ag | Substituted 6-(2-halogenphenyl)triazolopyrimidines |
| US20050272748A1 (en) * | 2002-11-15 | 2005-12-08 | Basf Aktiengesellschaft | 2-Mercapto-substituted triazolopyrimidines, methods for the production thereof, the use of the same for controlling patogenic fungi, and agents containing said compounds |
| PL376881A1 (pl) * | 2002-11-15 | 2006-01-09 | Basf Aktiengesellschaft | 2-Podstawione triazolopirymidyny, sposoby ich wytwarzania i związki pośrednie do ich wytwarzania, ich zastosowanie do zwalczania szkodliwych grzybów oraz zawierające je środki |
| EP1575958B1 (de) * | 2002-12-17 | 2008-02-06 | Basf Aktiengesellschaft | Fungizide triazolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen sowie sie enthaltende mittel |
| CN1729193A (zh) * | 2002-12-20 | 2006-02-01 | 巴斯福股份公司 | 三唑并嘧啶、其生产方法及其防治有害真菌的用途以及包含所述三唑并嘧啶的物质 |
| TW200504073A (en) * | 2003-04-17 | 2005-02-01 | Basf Ag | Bicyclic compounds and their use for controlling harmful fungi |
| AU2004246782A1 (en) * | 2003-06-18 | 2004-12-23 | Basf Aktiengesellschaft | Fungicidal mixtures based on a triazolopyrimidine derivative |
| MXPA05012795A (es) * | 2003-06-18 | 2006-02-22 | Basf Ag | Mezclas fungicidas. |
| 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 |
| MXPA06000034A (es) * | 2003-07-18 | 2006-03-21 | Basf Ag | Compuestos de 3-arilpiridina arilcondensados y su empleo para combatir hongos nocivos. |
| TW200517057A (en) * | 2003-09-22 | 2005-06-01 | Basf Ag | Fungicidal mixtures |
| JP2007512278A (ja) * | 2003-11-27 | 2007-05-17 | ビーエーエスエフ アクチェンゲゼルシャフト | トリアゾロピリミジン誘導体およびコナゾールに基づく殺菌混合物 |
| DE10357569A1 (de) * | 2003-12-10 | 2005-07-07 | Bayer Cropscience Ag | Pyrazolopyrimidine |
| DE10357568A1 (de) * | 2003-12-10 | 2005-07-07 | Bayer Cropscience Ag | Pyrazolopyrimidine |
| DE10357566A1 (de) * | 2003-12-10 | 2005-07-07 | Bayer Cropscience Ag | Pyrazolopyrimidine |
| DE10357565A1 (de) * | 2003-12-10 | 2005-07-07 | Bayer Cropscience Ag | Pyrazolopyrimidine |
| DE10357567A1 (de) * | 2003-12-10 | 2005-07-07 | Bayer Cropscience Ag | Pyrazolopyrimidine |
| EP1697364A1 (de) * | 2003-12-17 | 2006-09-06 | Basf Aktiengesellschaft | 6-pentafluorphenyl-triazolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bek mpfung von schadpilzen sowi e sie enthaltende mittel |
| JP2007534645A (ja) * | 2003-12-17 | 2007-11-29 | ビーエーエスエフ アクチェンゲゼルシャフト | ６−（２−クロロ−４−アルコキシフェニル）トリアゾロピリミジン、その製法、および有害菌類を防除するためのその使用、ならびにこれらの化合物を含む組成物 |
| DE10359445A1 (de) * | 2003-12-17 | 2005-07-28 | Enginion Ag | Wasserstoff-Verbrennungsmotor |
| TW200533670A (en) * | 2003-12-19 | 2005-10-16 | Basf Ag | 6-(aminocarbonylphenyl)triazolopyrimidines, their preparation and their use for controlling harmful fungi, and compositions comprising these compounds |
| PE20051089A1 (es) * | 2004-01-22 | 2006-01-25 | Novartis Ag | Derivados de pirazolo [1,5-a] pirimidin-7-il-amina como inhibidores de quinasa de proteina |
| BRPI0506967A (pt) * | 2004-01-23 | 2007-07-03 | Basf Ag | composto, processo para preparar o mesmo, agente fungicida, semente, e, processo para combater fungos nocivos fitopatogênicos |
| US20070197389A1 (en) * | 2004-02-25 | 2007-08-23 | Anja Schwogler | Azolopyrimidine compounds and use thereof for combating parasitic fungi |
| WO2005121146A2 (de) * | 2004-06-09 | 2005-12-22 | Basf Aktiengesellschaft | 1, 2, 4-TRIAZOLO[1,5a]PYRIMIDINE UND DEREN VERWENDUNG ZUR BEKÄMPFUNG VON PFLANZEN-PATHOGENEN PILZEN |
| MXPA06014145A (es) * | 2004-06-22 | 2007-03-07 | Basf Ag | Uso de 6-(2-tolil)-triazolopirimidinas como fungicidas, nuevas 6-(2-tolil)-triazolopirimidinas, procedimientos para su preparacion y el uso de las mismas para combatir hongos nocivos, asi como productos que las contienen. |
| CN1972948A (zh) * | 2004-06-25 | 2007-05-30 | 巴斯福股份公司 | 三唑并嘧啶化合物及其在防治病原性真菌中的用途 |
| CN1980935A (zh) * | 2004-07-08 | 2007-06-13 | 巴斯福股份公司 | 取代的6－苯基－7－氨基三唑并嘧啶、其生产方法、其在防治病原性真菌中的用途以及含有这些化合物的试剂 |
| EP1797097A1 (de) * | 2004-09-28 | 2007-06-20 | Basf Aktiengesellschaft | 7-aminomethyl-1,2,4-triazolo[1,5-a]pyrimidin-verbindungen und ihre verwendung zur bekämpfung von schadpilzen |
| EP1828190A1 (de) * | 2004-12-17 | 2007-09-05 | Basf Aktiengesellschaft | 7-amino-6-heteroaryl-1,2,4-triazoloý1,5-a¨pyrimidine und ihre verwendung zur bek[mpfung von schadpilzen |
| JP2007008864A (ja) * | 2005-06-30 | 2007-01-18 | Bayer Cropscience Ag | ピラゾロピリミジン誘導体及び農園芸用殺菌剤 |
| ATE442370T1 (de) * | 2005-07-27 | 2009-09-15 | Basf Se | Fungizide 6-phenyl-pyrazolopyrimidin-7-ylamine |
| JP2009502861A (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 | 殺菌性５−メチル−６−フェニルピラゾロピリミジン−７−イルアミン |
| WO2007012600A1 (de) * | 2005-07-27 | 2007-02-01 | Basf Aktiengesellschaft | Fungizide 5-alkyl-6-phenyl-pyrazolopyrimidin-7-ylamine |
| CA2616199C (en) * | 2005-07-27 | 2014-06-10 | Basf Aktiengesellschaft | Fungicidal mixtures based on azolopyrimidinylamines |
| WO2007012602A1 (de) * | 2005-07-27 | 2007-02-01 | Basf Aktiengesellschaft | Fungizide 5-methyl-6-phenyl-triazolopyrimidinylamine |
| BRPI0613912A2 (pt) * | 2005-07-27 | 2016-11-22 | Basf Ag | compostos, processo para preparar compostos, agente fungicida, semente, e, método para combater fungos nocivos fitopatogênicos |
| RU2008117298A (ru) * | 2005-10-06 | 2009-11-20 | Шеринг Корпорейшн (US) | Пиразолопиримидины как ингибиторы протеинкиназ |
| WO2007099092A1 (de) * | 2006-02-28 | 2007-09-07 | Basf Se | Substituierte 6-phenyl-7-amino-[1,2,4]-triazolo[1,5-a]pyrimidine und deren verwendung zur bekämpfung von schadpilzen |
| BRPI0716915B1 (pt) | 2006-09-18 | 2016-09-13 | Basf Se | mistura pesticida, composição pesticida, métodos para controlar fungos nocivos fitopatogênicos, para controlar insetos, aracnídeos ou nematódeos, para proteger plantas e para proteger semente, processo para a preparação de uma composição, e uso de uma mistura |
| CN101562980B (zh) | 2006-11-10 | 2014-04-16 | 巴斯夫欧洲公司 | 锐劲特的晶型 |
| EP2083628A1 (en) | 2006-11-10 | 2009-08-05 | Basf Se | Crystalline modification of fipronil |
| UA110598C2 (uk) | 2006-11-10 | 2016-01-25 | Басф Се | Спосіб одержання кристалічної модифікації фіпронілу |
| JP2010509275A (ja) | 2006-11-10 | 2010-03-25 | ビーエーエスエフ ソシエタス・ヨーロピア | フィプロニルの結晶変態 |
| JP2010511058A (ja) | 2006-11-29 | 2010-04-08 | アボット・ラボラトリーズ | ジアシルグリセロールｏ−アシルトランスフェラーゼ１型酵素の阻害薬 |
| NZ578205A (en) | 2007-01-19 | 2010-11-26 | Basf Se | Fungicidal mixtures of 1-methylpyrazol-4-ylcarboxylic acid anilides and azolopyrimidinylamines |
| EP2131658A2 (en) * | 2007-01-30 | 2009-12-16 | Basf Se | Method for improving plant health |
| KR20090105974A (ko) * | 2007-01-30 | 2009-10-07 | 바스프 에스이 | 아졸로피리미디닐아민 유도체 및 살곤충제 기재의 살충 혼합물 |
| MX2009007666A (es) | 2007-02-06 | 2009-07-27 | Basf Se | Mezclas de pesticidas. |
| KR20150066600A (ko) | 2007-09-20 | 2015-06-16 | 바스프 에스이 | 살진균성 균주 및 활성 화합물을 포함하는 조합물 |
| RU2012145413A (ru) | 2010-03-26 | 2014-05-10 | Басф Се | Фунгицидные смеси на основе азолопиримидиниламинов |
| WO2011131602A2 (en) | 2010-04-20 | 2011-10-27 | Basf Se | Fungicidal mixtures based on azolopyrimmidinylamines |
| WO2011138345A2 (en) | 2010-05-06 | 2011-11-10 | Basf Se | Fungicidal mixtures based on gallic acid esters |
| US20130267476A1 (en) | 2010-12-20 | 2013-10-10 | Basf Se | Pesticidal Active Mixtures Comprising Pyrazole Compounds |
| US20140200136A1 (en) | 2011-09-02 | 2014-07-17 | Basf Se | Agricultural mixtures comprising arylquinazolinone compounds |
| BR122019015104B1 (pt) | 2012-06-20 | 2020-04-07 | Basf Se | mistura pesticida, composição, composição agrícola, métodos para o combate ou controle das pragas de invertebrados, para a proteção dos vegetais em crescimento ou dos materias de propagação vegetal, para a proteção de material de propagação vegetal e uso de uma mistura pesticida |
| US9303034B2 (en) * | 2013-12-19 | 2016-04-05 | Novartis Ag | Compounds and compositions for the treatment of parasitic diseases |
| JP7254246B2 (ja) | 2019-11-25 | 2023-04-07 | アムジエン・インコーポレーテツド | デルタ－５デサチュラーゼ阻害剤としての複素環式化合物及び使用方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2553500A (en) * | 1946-08-01 | 1951-05-15 | Gen Aniline & Film Corp | Production of photographs in blue-black tones and compositions thereof |
| DD99794A1 (enExample) | 1966-09-27 | 1973-08-20 | ||
| DE1620694C3 (de) * | 1966-10-03 | 1982-04-15 | VEB Deutsches Hydrierwerk Rodleben, DDR 4501 Rodleben | Verfahren zur Herstellung von 5-Methyl-7-diäthylamino-s-triazolo [1,5-a] pyrimidin und seinen Salzen mit Säuren |
| FR2448542A1 (fr) | 1979-02-06 | 1980-09-05 | Landerlan Sa Lab | Derives de triazolapyrimidine utiles comme medicaments |
| US4483987A (en) * | 1983-06-20 | 1984-11-20 | G. D. Searle & Co. | 8-Substituted 7-phenyl-1,2,4-triazolo[2,3-c]pyrimidines-5-amines and amides |
-
1981
- 1981-08-01 DE DE19813130633 patent/DE3130633A1/de not_active Withdrawn
-
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 EP EP82106335A patent/EP0071792B1/de not_active Expired
- 1982-07-15 DE DE8282106335T patent/DE3262143D1/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 AU AU86659/82A patent/AU553663B2/en not_active Ceased
- 1982-07-30 ZA ZA825498A patent/ZA825498B/xx unknown
- 1982-07-30 DK DK341682A patent/DK160020C/da not_active IP Right Cessation
- 1982-07-30 HU HU822474A patent/HU188325B/hu 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
-
1984
- 1984-09-18 US US06/651,660 patent/US4567263A/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004000844A1 (de) * | 2002-05-29 | 2003-12-31 | Bayer Cropscience Aktiengesellschaft | Pyrazolopyrimidine und ihre verwendung zur bekämpfung von schädlichen organismen |
| RU2331643C2 (ru) * | 2002-05-29 | 2008-08-20 | Байер Кропсайенс Аг | Пиразолопиримидины и средство, обладающее фунгицидной и бактерицидной активностью для борьбы с вредными организмами, на их основе |
| US7629294B2 (en) | 2004-02-20 | 2009-12-08 | Bayer Cropscience Lp | Pyrazolopyrimidines |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0071792B1 (de) | 1985-01-30 |
| IE821848L (en) | 1983-02-01 |
| ATE11539T1 (de) | 1985-02-15 |
| JPH0261955B2 (enExample) | 1990-12-21 |
| JPS5843974A (ja) | 1983-03-14 |
| DE3262143D1 (en) | 1985-03-14 |
| AU8665982A (en) | 1983-02-10 |
| DK160020B (da) | 1991-01-14 |
| IE53269B1 (en) | 1988-09-28 |
| CS226748B2 (en) | 1984-04-16 |
| IL66358A0 (en) | 1982-11-30 |
| US4567263A (en) | 1986-01-28 |
| EP0071792A3 (en) | 1983-04-06 |
| HU188325B (en) | 1986-04-28 |
| AU553663B2 (en) | 1986-07-24 |
| DK160020C (da) | 1991-06-03 |
| GR76193B (enExample) | 1984-08-03 |
| EP0071792A2 (de) | 1983-02-16 |
| DD202093A5 (de) | 1983-08-31 |
| ZA825498B (en) | 1983-07-27 |
| DK341682A (da) | 1983-02-02 |
| CA1180329A (en) | 1985-01-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3130633A1 (de) | 7-amino-azolo(1,5-a)pyrimidine und diese enthaltende fungizide | |
| EP0141317B1 (de) | 7-Amino-azolo[1,5-a]-pyrimidine und diese enthaltende Fungizide | |
| EP0119539A2 (de) | Fungizide Mittel, substituierte Glucopyranosylamine und Verfahren zur Bekämpfung von Pilzen | |
| EP0013360B1 (de) | N-substituierte Carbonsäureanilide, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide | |
| EP0275520A1 (de) | Substituierte 1,8-Naphthyridin-Derivate und diese enthaltende Fungizide | |
| EP0135076B1 (de) | Pyridazinon-Derivate, Verfahren zu ihrer Herstellung un ihre Verwendung als Fungizide | |
| DD249624A5 (de) | Fungizide mittel | |
| EP0057365A2 (de) | Vinylazole, Verfahren zu ihrer Herstellung und ihre Verwendung bei der Bekämpfung von Pilzen | |
| EP0191443B1 (de) | 4-Aminopyrimidine und diese enthaltende Fungizide | |
| EP0251083B1 (de) | 4-Aminopyrimidinderivate | |
| EP0098486A1 (de) | Chinolinderivate, Verfahren zu ihrer Herstellung, diese enthaltende Mikrobizide und ihre Verwendung zur Bekämpfung von Pilzen | |
| EP0065723B1 (de) | N-substituierte 2-Methylnaphthylamide, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Pilzen | |
| EP0056860B1 (de) | Substituierte Azolyl-glykolsulfonate, diese enthaltende Fungizide und Verfahren zu ihrer Herstellung | |
| EP0056125B1 (de) | Keten-O,N-acetale, Verfahren zu ihrer Herstellung, diese enthaltende Fungizide und ihre Verwendung zur Bekämpfung von Pilzen | |
| EP0054147B1 (de) | Isatogenderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide | |
| EP0019153A1 (de) | Carbinolether, Verfahren zu ihrer Herstellung und diese enthaltende Fungizide | |
| EP0010691A1 (de) | Neue 1,2,4-Triazolderivate Verfahren zu ihrer Herstellung, ihre Verwendung zur Herstellung von Pflanzenschutzmitteln, Verfahren zur Herstellung von Fungiziden und Verfahren zur Bekämpfung von Fungi sowie fungizide Mittel | |
| DE3021834A1 (de) | Azolyl-4-nitro-2-trichlormethyl-benzolsulfone, ihre herstellung und verwendung | |
| EP0101974A1 (de) | Thiadiazinone, Verfahren zu ihrer Herstellung und diese enthaltende Fungizide | |
| DE3327013A1 (de) | 2-cyan-2-oxyimino-n-carbamoylacetamide, diese enthaltende fungizide und verfahren zu ihrer herstellung | |
| CH628209A5 (de) | Fungizides mittel. | |
| EP0031029A1 (de) | Gamma-Azolyl-Verbindungen enthaltende Fungizide und deren Verwendung | |
| DE2540872A1 (de) | Hydantoin-derivate | |
| EP0074071A1 (de) | Oxalamide, Verfahren zu ihrer Herstellung und diese enthaltende Fungizide | |
| EP0076382A2 (de) | N-Alkinyl-N-naphthylamide, Verfahren zu ihrer Herstellung und diese enthaltende Fungizide |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |