DD202092A5 - Fungizides mittel - Google Patents

Fungizides mittel Download PDF

Info

Publication number: DD202092A5
Authority: DD; German Democratic Republic
Prior art keywords: acetophenone; pyrazinyl; dichloro; pyridyl; chloro
Prior art date: 1980-10-10

Application number

DD81233896A

Other languages

German (de)

English (en)

Inventor

Franz Dorn

Original Assignee

Hoffmann La Roche

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.)

1980-10-10

Filing date

1981-10-05

Publication date

1983-08-31

1981-10-05 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1983-08-31 Publication of DD202092A5 publication Critical patent/DD202092A5/de

Links

239000000417 fungicide Substances 0.000 title claims abstract description 15
150000001875 compounds Chemical class 0.000 claims abstract description 57
150000003839 salts Chemical class 0.000 claims abstract description 19
239000002253 acid Substances 0.000 claims abstract description 16
238000000034 method Methods 0.000 claims abstract description 15
238000002360 preparation method Methods 0.000 claims abstract description 13
241000233866 Fungi Species 0.000 claims abstract description 12
238000003898 horticulture Methods 0.000 claims abstract description 9
239000003795 chemical substances by application Substances 0.000 claims abstract description 7
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 24
239000000203 mixture Substances 0.000 claims description 12
-1 dichloro-2- (2-pyrazinyl) -propiophenone Chemical compound 0.000 claims description 10
230000000855 fungicidal effect Effects 0.000 claims description 10
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
239000012876 carrier material Substances 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 5
125000001475 halogen functional group Chemical group 0.000 claims description 4
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 3
238000002156 mixing Methods 0.000 claims description 3
150000002923 oximes Chemical class 0.000 claims description 3
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
JOUGEUWUSSLCLD-UHFFFAOYSA-N 1-(4-chlorophenyl)-n-methoxy-2-pyridin-3-ylethanimine Chemical compound C=1C=C(Cl)C=CC=1C(=NOC)CC1=CC=CN=C1 JOUGEUWUSSLCLD-UHFFFAOYSA-N 0.000 claims description 2
239000000463 material Substances 0.000 claims 3
XATBRNBYTKPFCG-UHFFFAOYSA-N 2,2-dichloro-n-methoxy-1-phenyl-2-pyridin-3-ylethanimine Chemical compound C=1C=CN=CC=1C(Cl)(Cl)C(=NOC)C1=CC=CC=C1 XATBRNBYTKPFCG-UHFFFAOYSA-N 0.000 claims 1
239000004480 active ingredient Substances 0.000 abstract description 16
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 14
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 7
150000003216 pyrazines Chemical class 0.000 abstract description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 8
XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 8
CAWHJQAVHZEVTJ-UHFFFAOYSA-N methylpyrazine Chemical compound CC1=CN=CC=N1 CAWHJQAVHZEVTJ-UHFFFAOYSA-N 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000007921 spray Substances 0.000 description 6
239000007858 starting material Substances 0.000 description 6
CGZQCZNRBCLEOH-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-2-pyridin-3-ylethanone Chemical compound ClC1=CC(Cl)=CC=C1C(=O)CC1=CC=CN=C1 CGZQCZNRBCLEOH-UHFFFAOYSA-N 0.000 description 5
241000196324 Embryophyta Species 0.000 description 5
241000221785 Erysiphales Species 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
239000013543 active substance Substances 0.000 description 5
239000002585 base Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
KUZOAJKWVPACQX-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-2-pyrazin-2-ylethanone Chemical compound ClC1=CC(Cl)=CC=C1C(=O)CC1=CN=CC=N1 KUZOAJKWVPACQX-UHFFFAOYSA-N 0.000 description 4
KBCBKIPUEHCLJB-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-pyrazin-2-ylethanone Chemical compound C1=CC(Cl)=CC=C1C(=O)CC1=CN=CC=N1 KBCBKIPUEHCLJB-UHFFFAOYSA-N 0.000 description 4
239000005995 Aluminium silicate Substances 0.000 description 4
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 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
125000003342 alkenyl group Chemical group 0.000 description 4
235000012211 aluminium silicate Nutrition 0.000 description 4
239000004495 emulsifiable concentrate Substances 0.000 description 4
KVFIJIWMDBAGDP-UHFFFAOYSA-N ethylpyrazine Chemical compound CCC1=CN=CC=N1 KVFIJIWMDBAGDP-UHFFFAOYSA-N 0.000 description 4
125000005843 halogen group Chemical group 0.000 description 4
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 4
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
BVUNKIYUJIIEEX-UHFFFAOYSA-N n-[1-(2,4-dichlorophenyl)-2-pyridin-3-ylethylidene]hydroxylamine Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=NO)CC1=CC=CN=C1 BVUNKIYUJIIEEX-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
CKPCAYZTYMHQEX-JXAWBTAJSA-N (z)-1-(2,4-dichlorophenyl)-n-methoxy-2-pyridin-3-ylethanimine Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=N/OC)\CC1=CC=CN=C1 CKPCAYZTYMHQEX-JXAWBTAJSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000012043 crude product Substances 0.000 description 3
LRCFXGAMWKDGLA-UHFFFAOYSA-N dioxosilane;hydrate Chemical compound O.O=[Si]=O LRCFXGAMWKDGLA-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000003921 oil Substances 0.000 description 3
230000003032 phytopathogenic effect Effects 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
229960004029 silicic acid Drugs 0.000 description 3
229960001866 silicon dioxide Drugs 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
DHIYWPQTECHUNX-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-pyrazin-2-ylpropan-1-one Chemical compound C=1N=CC=NC=1C(C)C(=O)C1=CC=C(Cl)C=C1 DHIYWPQTECHUNX-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
206010039509 Scab Diseases 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
241000221577 Uromyces appendiculatus Species 0.000 description 2
125000000304 alkynyl group Chemical group 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
230000001588 bifunctional effect Effects 0.000 description 2
OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000004359 castor oil Substances 0.000 description 2
235000019438 castor oil Nutrition 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
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 2
229940093915 gynecological organic acid Drugs 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000000155 melt Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
IOUXLAZQWNNGRA-UHFFFAOYSA-N n-[1-(4-chlorophenyl)-2-pyrazin-2-ylethylidene]hydroxylamine Chemical compound C=1C=C(Cl)C=CC=1C(=NO)CC1=CN=CC=N1 IOUXLAZQWNNGRA-UHFFFAOYSA-N 0.000 description 2
229910017604 nitric acid Inorganic materials 0.000 description 2
NUXCOKIYARRTDC-UHFFFAOYSA-N o-ethylhydroxylamine;hydron;chloride Chemical compound Cl.CCON NUXCOKIYARRTDC-UHFFFAOYSA-N 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 2
239000003586 protic polar solvent Substances 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
150000003460 sulfonic acids Chemical class 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
AYWDUWKFFSUEFE-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-2-pyrazin-2-ylpropan-1-one Chemical compound C=1N=CC=NC=1C(C)C(=O)C1=CC=C(Cl)C=C1Cl AYWDUWKFFSUEFE-UHFFFAOYSA-N 0.000 description 1
PVPPSYNNEIDORF-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-n-ethoxy-2-pyridin-3-ylethanimine Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=NOCC)CC1=CC=CN=C1 PVPPSYNNEIDORF-UHFFFAOYSA-N 0.000 description 1
KAUVMPWDSMAISH-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-n-methoxy-2-pyrazin-2-ylpropan-1-imine Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=NOC)C(C)C1=CN=CC=N1 KAUVMPWDSMAISH-UHFFFAOYSA-N 0.000 description 1
NVKWOGAKCQFEHR-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-n-prop-2-ynoxy-2-pyrazin-2-ylethanimine Chemical compound ClC1=CC(Cl)=CC=C1C(=NOCC#C)CC1=CN=CC=N1 NVKWOGAKCQFEHR-UHFFFAOYSA-N 0.000 description 1
XHDPNHNJYMVCCO-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-n-prop-2-ynoxy-2-pyridin-3-ylethanimine Chemical compound ClC1=CC(Cl)=CC=C1C(=NOCC#C)CC1=CC=CN=C1 XHDPNHNJYMVCCO-UHFFFAOYSA-N 0.000 description 1
BSBDMMWCKABSKX-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-n-propan-2-yloxy-2-pyrazin-2-ylethanimine Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=NOC(C)C)CC1=CN=CC=N1 BSBDMMWCKABSKX-UHFFFAOYSA-N 0.000 description 1
RMGGNVKRVNWVCV-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-n-propan-2-yloxy-2-pyridin-3-ylethanimine Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=NOC(C)C)CC1=CC=CN=C1 RMGGNVKRVNWVCV-UHFFFAOYSA-N 0.000 description 1
YHPUJWQWBMOWSZ-UHFFFAOYSA-N 1-(2-chlorophenyl)-2-pyrazin-2-ylethanone Chemical compound ClC1=CC=CC=C1C(=O)CC1=CN=CC=N1 YHPUJWQWBMOWSZ-UHFFFAOYSA-N 0.000 description 1
CCIFCWHNVQXPTI-UHFFFAOYSA-N 1-(2-chlorophenyl)-n-methoxy-2-pyrazin-2-ylethanimine Chemical compound C=1C=CC=C(Cl)C=1C(=NOC)CC1=CN=CC=N1 CCIFCWHNVQXPTI-UHFFFAOYSA-N 0.000 description 1
YQBAOXWHMUDREK-UHFFFAOYSA-N 1-(4-bromophenyl)-2-pyrazin-2-ylethanone Chemical compound C1=CC(Br)=CC=C1C(=O)CC1=CN=CC=N1 YQBAOXWHMUDREK-UHFFFAOYSA-N 0.000 description 1
ACWFIYYVDCWFPR-UHFFFAOYSA-N 1-(4-bromophenyl)-n-methoxy-2-pyrazin-2-ylethanimine Chemical compound C=1C=C(Br)C=CC=1C(=NOC)CC1=CN=CC=N1 ACWFIYYVDCWFPR-UHFFFAOYSA-N 0.000 description 1
XPSQHYPYPLUYAC-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-pyridin-3-ylethanone Chemical compound C1=CC(Cl)=CC=C1C(=O)CC1=CC=CN=C1 XPSQHYPYPLUYAC-UHFFFAOYSA-N 0.000 description 1
BDJBVPOPIPGRSP-UHFFFAOYSA-N 1-(4-chlorophenyl)-n-ethoxy-2-pyrazin-2-ylethanimine Chemical compound C=1C=C(Cl)C=CC=1C(=NOCC)CC1=CN=CC=N1 BDJBVPOPIPGRSP-UHFFFAOYSA-N 0.000 description 1
USGFTVNSUJEMMH-UHFFFAOYSA-N 1-(4-chlorophenyl)-n-methoxy-2-pyrazin-2-ylethanimine Chemical compound C=1C=C(Cl)C=CC=1C(=NOC)CC1=CN=CC=N1 USGFTVNSUJEMMH-UHFFFAOYSA-N 0.000 description 1
GDANOLXKBFVBJB-UHFFFAOYSA-N 1-(4-chlorophenyl)-n-methoxy-2-pyrazin-2-ylpropan-1-imine Chemical compound C=1C=C(Cl)C=CC=1C(=NOC)C(C)C1=CN=CC=N1 GDANOLXKBFVBJB-UHFFFAOYSA-N 0.000 description 1
DDUCWCUOGZLMTN-UHFFFAOYSA-N 1-(4-chlorophenyl)-n-prop-2-ynoxy-2-pyrazin-2-ylethanimine Chemical compound C1=CC(Cl)=CC=C1C(=NOCC#C)CC1=CN=CC=N1 DDUCWCUOGZLMTN-UHFFFAOYSA-N 0.000 description 1
XZOODJULVBPISP-UHFFFAOYSA-N 1-(4-fluorophenyl)-2-pyrazin-2-ylethanone Chemical compound C1=CC(F)=CC=C1C(=O)CC1=CN=CC=N1 XZOODJULVBPISP-UHFFFAOYSA-N 0.000 description 1
ATCRIUVQKHMXSH-UHFFFAOYSA-M 2,4-dichlorobenzoate Chemical compound [O-]C(=O)C1=CC=C(Cl)C=C1Cl ATCRIUVQKHMXSH-UHFFFAOYSA-M 0.000 description 1
NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
IKCLCGXPQILATA-UHFFFAOYSA-M 2-chlorobenzoate Chemical compound [O-]C(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-M 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
241001480061 Blumeria graminis Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
XHNZTOHDRQYGOX-UHFFFAOYSA-N CON=C(C(C1=NC=CN=C1)(Cl)Cl)C1=CC=CC=C1 Chemical compound CON=C(C(C1=NC=CN=C1)(Cl)Cl)C1=CC=CC=C1 XHNZTOHDRQYGOX-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
241001157813 Cercospora Species 0.000 description 1
241001600095 Coniophora puteana Species 0.000 description 1
241001529717 Corticium <basidiomycota> Species 0.000 description 1
240000008067 Cucumis sativus Species 0.000 description 1
235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
241000371644 Curvularia ravenelii Species 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
241001492300 Gloeophyllum trabeum Species 0.000 description 1
241000896246 Golovinomyces cichoracearum Species 0.000 description 1
241001181537 Hemileia Species 0.000 description 1
241001181532 Hemileia vastatrix Species 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
241000188250 Idas Species 0.000 description 1
101150057104 MCIDAS gene Proteins 0.000 description 1
241000276489 Merlangius merlangus Species 0.000 description 1
241001337928 Podosphaera leucotricha Species 0.000 description 1
241000896203 Podosphaera pannosa Species 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
241000221300 Puccinia Species 0.000 description 1
241001123561 Puccinia coronata Species 0.000 description 1
241001123569 Puccinia recondita Species 0.000 description 1
241000221535 Pucciniales Species 0.000 description 1
241001361634 Rhizoctonia Species 0.000 description 1
241000220317 Rosa Species 0.000 description 1
241001533598 Septoria Species 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
241000722133 Tilletia Species 0.000 description 1
241000221576 Uromyces Species 0.000 description 1
241000221566 Ustilago Species 0.000 description 1
241000228452 Venturia inaequalis Species 0.000 description 1
241000589652 Xanthomonas oryzae Species 0.000 description 1
230000000895 acaricidal effect Effects 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000003899 bactericide agent Substances 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-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
235000013339 cereals Nutrition 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
229960004106 citric acid Drugs 0.000 description 1
238000007865 diluting Methods 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
235000013399 edible fruits Nutrition 0.000 description 1
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
229960002598 fumaric acid Drugs 0.000 description 1
238000000227 grinding Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002431 hydrogen Chemical group 0.000 description 1
XIQUJVRFXPBMHS-UHFFFAOYSA-N hydron;o-prop-2-enylhydroxylamine;chloride Chemical compound Cl.NOCC=C XIQUJVRFXPBMHS-UHFFFAOYSA-N 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000000749 insecticidal effect Effects 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
229960000448 lactic acid Drugs 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
229940098895 maleic acid Drugs 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
VCRWILYAWSRHBN-UHFFFAOYSA-N methyl 2,4-dichlorobenzoate Chemical compound COC(=O)C1=CC=C(Cl)C=C1Cl VCRWILYAWSRHBN-UHFFFAOYSA-N 0.000 description 1
CZNGTXVOZOWWKM-UHFFFAOYSA-N methyl 4-bromobenzoate Chemical compound COC(=O)C1=CC=C(Br)C=C1 CZNGTXVOZOWWKM-UHFFFAOYSA-N 0.000 description 1
LXNFVVDCCWUUKC-UHFFFAOYSA-N methyl 4-chlorobenzoate Chemical compound COC(=O)C1=CC=C(Cl)C=C1 LXNFVVDCCWUUKC-UHFFFAOYSA-N 0.000 description 1
MSEBQGULDWDIRW-UHFFFAOYSA-N methyl 4-fluorobenzoate Chemical compound COC(=O)C1=CC=C(F)C=C1 MSEBQGULDWDIRW-UHFFFAOYSA-N 0.000 description 1
CUKYGXFNZUNZLN-UHFFFAOYSA-N n-[1-(2,4-dichlorophenyl)-2-pyrazin-2-ylethylidene]hydroxylamine Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=NO)CC1=CN=CC=N1 CUKYGXFNZUNZLN-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
XTEGVFVZDVNBPF-UHFFFAOYSA-L naphthalene-1,5-disulfonate(2-) Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1S([O-])(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-L 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
KPTCZURLWZSRKB-UHFFFAOYSA-N o-prop-2-enylhydroxylamine Chemical compound NOCC=C KPTCZURLWZSRKB-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
238000005554 pickling Methods 0.000 description 1
230000008635 plant growth Effects 0.000 description 1
239000005648 plant growth regulator Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229960001367 tartaric acid Drugs 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/53—Nitrogen atoms
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms

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)
Pyridine Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)

DD81233896A 1980-10-10 1981-10-05 Fungizides mittel DD202092A5 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH758480		1980-10-10
CH464281		1981-07-15

Publications (1)

Publication Number	Publication Date
DD202092A5 true DD202092A5 (de)	1983-08-31

Family

ID=25695975

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD81233896A DD202092A5 (de)	1980-10-10	1981-10-05	Fungizides mittel

Country Status (15)

Country	Link
US (1)	US4605656A (fr)
EP (1)	EP0049854B1 (fr)
AR (1)	AR231633A1 (fr)
AU (1)	AU552881B2 (fr)
BR (1)	BR8106236A (fr)
CA (1)	CA1225092A (fr)
DD (1)	DD202092A5 (fr)
DE (1)	DE3168350D1 (fr)
ES (2)	ES506141A0 (fr)
GB (1)	GB2085007B (fr)
HU (1)	HU187375B (fr)
KE (1)	KE3484A (fr)
NZ (1)	NZ198534A (fr)
OA (1)	OA06918A (fr)
PL (1)	PL233387A1 (fr)

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH650253A5 (de) *	1982-03-26	1985-07-15	Hoffmann La Roche	Pyridin- und pyrazin-derivate und ihre verwendung als fungizide wirkstoffe.
IT1172404B (it) *	1982-03-31	1987-06-18	Hoffmann La Roche	Composti eterociclici
US5036074A (en) *	1989-03-01	1991-07-30	Ciba-Geigy Corporation	Certain 2,4-dichloro-phenyl(loweralkylidene) pyridines having fungicidal activity
EP0445069A1 (fr) *	1990-02-16	1991-09-04	Ciba-Geigy Ag	Composés hétérocycliques
DE4018260A1 (de) *	1990-06-07	1991-12-12	Basf Ag	Derivate des (beta)-picolins und diese enthaltende pflanzenschutzmittel
US5493024A (en) *	1991-04-11	1996-02-20	Dowelanco	3,4,N-trisubstituted-4,5-dihydro-1H-pyrazole-1-carboxamides and their use as insectioides
BRPI0509093A (pt) *	2004-04-27	2007-08-28	Basf Aktiengeeellschaft	misturas fungicidas para combater fungos nocivos fitopatogênicos, agente, processo para combater fungos nocivos, semente, e, uso dos compostos
CA2661170A1 (fr)	2006-09-18	2008-03-27	Basf Se	Melanges pesticides
WO2008071714A1 (fr)	2006-12-15	2008-06-19	Rohm And Haas Company	Mélanges comprenant du 1-méthylcyclopropène
BR122019020360B1 (pt)	2007-02-06	2020-08-18	Basf Se	misturas, composição pesticida, método para controlar fungos nocivos fitopatogênicos, método para proteger plantas do ataque ou infestação pelos insetos, acarídeos ou nematódeos e método para proteger semente
EA017621B1 (ru)	2007-04-23	2013-01-30	Басф Се	Повышение продуктивности растений путем комбинирования химических веществ с трансгенными модификациями
ES2381320T3 (es)	2007-09-26	2012-05-25	Basf Se	Composiciones fungicidas ternarias que comprenden boscalida y clorotalonil
WO2011026796A1 (fr)	2009-09-01	2011-03-10	Basf Se	Mélanges fongicides synergiques contenant des lactylates et procédé de lutte contre des champignons phytopathogènes
EA201300731A1 (ru)	2010-12-20	2014-01-30	Басф Се	Пестицидно активные смеси, которые содержат соединения пиразола
EP2481284A3 (fr)	2011-01-27	2012-10-17	Basf Se	Mélanges de pesticides
EP3378313A1 (fr)	2011-03-23	2018-09-26	Basf Se	Compositions contenant composés polymères ioniques comportant des groupes imidazolium
JP2014525424A (ja)	2011-09-02	2014-09-29	ビーエーエスエフソシエタス・ヨーロピア	アリールキナゾリノン化合物を含む農業用混合物
ES2660132T3 (es)	2012-06-20	2018-03-20	Basf Se	Compuestos de pirazol plaguicidas
US20150257383A1 (en)	2012-10-12	2015-09-17	Basf Se	Method for combating phytopathogenic harmful microbes on cultivated plants or plant propagation material
CA2894264C (fr)	2012-12-20	2023-03-07	BASF Agro B.V.	Compositions comprenant un compose triazole
EP2783569A1 (fr)	2013-03-28	2014-10-01	Basf Se	Compositions comprenant un composé de triazole
EP2835052A1 (fr)	2013-08-07	2015-02-11	Basf Se	Mélanges fongicides comprenant des pyrimidines fongicides
EP3046915A1 (fr)	2013-09-16	2016-07-27	Basf Se	Composés pyrimidines fongicides
WO2015036059A1 (fr)	2013-09-16	2015-03-19	Basf Se	Composés fongicides de pyrimidine
EP2979549A1 (fr)	2014-07-31	2016-02-03	Basf Se	Procédé pour améliorer la santé d'une plante
AU2015334829B2 (en)	2014-10-24	2019-09-12	Basf Se	Non-amphoteric, quaternisable and water-soluble polymers for modifying the surface charge of solid particles

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3205234A (en) *	1961-06-30	1965-09-07	Upjohn Co	Nu-oxides of pyridyl ketone omicron-hydrocarbonoximes
US3167563A (en) *	1962-03-05	1965-01-26	Upjohn Co	O-(ring-substituted) benzyl ethers of acyl-pyridineoxime 1-oxides
DE2723942C2 (de) *	1977-05-27	1982-11-11	Basf Ag, 6700 Ludwigshafen	ω-(1,2,4-Triazol-1-yl) acetophenonoximäther
GB2015524A (en) *	1978-03-06	1979-09-12	Ici Ltd	Pyridine derivatives
US4352804A (en) *	1978-07-25	1982-10-05	Acf Chemiefarma Nv	Oxime ethers, their preparation and pharmaceutical compositions containing them
US4297359A (en) *	1978-07-25	1981-10-27	Acf Chemiefarma Nv	Anti-ulcer compositions containing certain pyridyl oxime ethers
US4263305A (en) *	1979-03-12	1981-04-21	Interx Research Corporation	Novel pyridiniumaldoximes having micellar characteristics
US4244959A (en) *	1979-07-02	1981-01-13	Chevron Research Company	Fungicidal O-acyl (alpha-nitro-formaldoxime) and (alpha-halo-formaldoxime)-pyridines
US4305947A (en) *	1980-08-26	1981-12-15	Survival Technology, Inc.	Stable aqueous solutions of pralidoxime salts

1981
- 1981-08-21 CA CA000384356A patent/CA1225092A/fr not_active Expired
- 1981-09-29 BR BR8106236A patent/BR8106236A/pt unknown
- 1981-10-02 NZ NZ198534A patent/NZ198534A/en unknown
- 1981-10-05 DD DD81233896A patent/DD202092A5/de unknown
- 1981-10-06 EP EP81107990A patent/EP0049854B1/fr not_active Expired
- 1981-10-06 DE DE8181107990T patent/DE3168350D1/de not_active Expired
- 1981-10-07 HU HU812893A patent/HU187375B/hu unknown
- 1981-10-08 OA OA57513A patent/OA06918A/fr unknown
- 1981-10-09 AU AU76185/81A patent/AU552881B2/en not_active Expired
- 1981-10-09 AR AR287049A patent/AR231633A1/es active
- 1981-10-09 PL PL23338781A patent/PL233387A1/xx unknown
- 1981-10-09 GB GB8130521A patent/GB2085007B/en not_active Expired
- 1981-10-09 ES ES506141A patent/ES506141A0/es active Granted
1982
- 1982-05-11 ES ES512076A patent/ES8302660A1/es not_active Expired
1983
- 1983-10-21 US US06/736,061 patent/US4605656A/en not_active Expired - Lifetime
1984
- 1984-12-07 KE KE3484A patent/KE3484A/xx unknown

Also Published As

Publication number	Publication date
GB2085007A (en)	1982-04-21
ES512076A0 (es)	1983-02-01
KE3484A (en)	1985-01-25
OA06918A (fr)	1983-05-31
HU187375B (en)	1985-12-28
PL233387A1 (fr)	1982-12-20
ES8301945A1 (es)	1982-12-16
EP0049854A2 (fr)	1982-04-21
ES8302660A1 (es)	1983-02-01
ES506141A0 (es)	1982-12-16
AU552881B2 (en)	1986-06-26
EP0049854A3 (en)	1982-04-28
DE3168350D1 (en)	1985-02-28
AU7618581A (en)	1982-04-22
US4605656A (en)	1986-08-12
AR231633A1 (es)	1985-01-31
GB2085007B (en)	1984-08-08
EP0049854B1 (fr)	1985-01-16
NZ198534A (en)	1985-03-20
CA1225092A (fr)	1987-08-04
BR8106236A (pt)	1982-06-15

Publication	Publication Date	Title
EP0049854B1 (fr)	1985-01-16	Dérivés de pyridine et de pyrazine, préparation de ces composés, fongicides qui contiennent ces composés comme principe actif et utilisation de tels composés ou moyens comme fongicides en agriculture et en horticulture
DE2429523C2 (fr)	1988-07-21
DE2324010A1 (de)	1975-01-16	Triazolyl-0,n-acetale, verfahren zu ihrer herstellung und ihre fungizide verwendung
DE2742173A1 (de)	1979-03-29	Phenoxy-pyridinyl(pyrimidinyl)-alkanole, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide
DD206728A5 (de)	1984-02-08	Fungizide mittel
DE2652313A1 (de)	1978-05-18	Triazolderivate
DD140411A5 (de)	1980-03-05	Fungizide mittel
EP0071009B1 (fr)	1987-02-04	Dérivés d'alcinyl-azol fongicide et leur utilisation
DE1793229B2 (de)	1979-03-08	Cyclohexylpentadiensäurederivate, ihre Herstellung und ihre Verwendung als Wachstumsregulatoren für Pflanzen
EP0016974A1 (fr)	1980-10-15	Dérivés de la pyridine substituée en position 3, procédé pour leur préparation, leur utilisation comme fongicides et composés intermédiaires
EP0158205A2 (fr)	1985-10-16	(1,2,4-Triazol-1-yl)-méthyl carbinoles
DD158850A5 (de)	1983-02-09	Aminopropanol-derivate,verfahren zu ihrer herstellung und ihre verwendung als fungizide
DE2624529A1 (de)	1977-12-22	Aminomethylazol-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide und zur regulierung des pflanzenwachstums
EP0062238A1 (fr)	1982-10-13	Dérivés de 1,3-dioxolanes, leur préparation, fongicides contenant ces composés comme principe actif et utilisation de tels composés ou agents fongicides pour combattre les champignons en agriculture et en jardinage
EP0129798A1 (fr)	1985-01-02	Composés d'azole fongicides, leur préparation et leur utilisation
DD215929A5 (de)	1984-11-28	Fungizide mittel
DE2827968A1 (de)	1980-01-10	Sulfenylierte carbamoyl-triazolyl- o,n-acetale, verfahren zu ihrer herstellung und ihre verwendung als fungizide
DD158848A5 (de)	1983-02-09	Substituierte phenyl-trazolyl-vinyl-ketone,verfahren zu ihrer herstellung sowie ihre verwendung als fungizide
DE3310148A1 (de)	1983-10-06	Heterocyclische verbindungen
DE3321158A1 (de)	1984-12-13	Azolylmethyl-thienyl-carbinol-derivate
DD221343A5 (de)	1985-04-24	Fungizide mittel
DD236869A5 (de)	1986-06-25	Fungizide mittel
EP0073331B1 (fr)	1986-04-09	5-Aryloxy-5-azolyl-3,3-diméthyl-1-pentène-4-ones et -ols, leur procédé de synthèse et leur application comme fongicides
CH651552A5 (en)	1985-09-30	Heterocyclic compounds
DD248275A5 (de)	1987-08-05	Fungizide und pflanzenwuchsregulierende mittel