CA1146596A - Derives de trichlorovinyl-cetones, microbicides - Google Patents

Derives de trichlorovinyl-cetones, microbicides

Info

Publication number: CA1146596A
Authority: CA; Canada
Prior art keywords: formula; microorganisms; plants; trichlorovinyl; parts
Prior art date: 1978-11-06
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.): Expired

Application number

CA000402107A

Other languages

English (en)

Inventor

Elmar Sturm

Robert Nyfeler

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

Novartis AG

Original Assignee

Ciba Geigy Investments Ltd

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.)

1978-11-06

Filing date

1982-04-30

Publication date

1983-05-17

1979-11-02 Priority claimed from CA000339094A external-priority patent/CA1140568A/fr

1982-04-30 Application filed by Ciba Geigy Investments Ltd filed Critical Ciba Geigy Investments Ltd

1982-04-30 Priority to CA000402107A priority Critical patent/CA1146596A/fr

1983-05-17 Application granted granted Critical

1983-05-17 Publication of CA1146596A publication Critical patent/CA1146596A/fr

Status Expired legal-status Critical Current

Links

MQGVZPCVUTWNMB-UHFFFAOYSA-N 1,1,2,4,5,5-hexachloropenta-1,4-dien-3-one Chemical class ClC(Cl)=C(Cl)C(=O)C(Cl)=C(Cl)Cl MQGVZPCVUTWNMB-UHFFFAOYSA-N 0.000 title claims description 3
230000003641 microbiacidal effect Effects 0.000 title abstract description 5
150000001875 compounds Chemical class 0.000 claims abstract description 63
239000000460 chlorine Chemical group 0.000 claims abstract description 55
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
239000001257 hydrogen Substances 0.000 claims abstract description 15
241000233866 Fungi Species 0.000 claims abstract description 13
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 9
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 9
229910052794 bromium Inorganic materials 0.000 claims abstract description 9
229910052801 chlorine Inorganic materials 0.000 claims abstract description 9
150000002576 ketones Chemical class 0.000 claims abstract description 8
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 7
229910052731 fluorine Inorganic materials 0.000 claims abstract description 7
239000011737 fluorine Chemical group 0.000 claims abstract description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 7
230000003032 phytopathogenic effect Effects 0.000 claims abstract description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
241000894006 Bacteria Species 0.000 claims abstract description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 3
238000000034 method Methods 0.000 claims description 20
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
150000002431 hydrogen Chemical class 0.000 claims description 8
239000002841 Lewis acid Substances 0.000 claims description 7
150000007517 lewis acids Chemical class 0.000 claims description 7
BCOSEZGCLGPUSL-UHFFFAOYSA-N 2,3,3-trichloroprop-2-enoyl chloride Chemical compound ClC(Cl)=C(Cl)C(Cl)=O BCOSEZGCLGPUSL-UHFFFAOYSA-N 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
JVJQPDTXIALXOG-UHFFFAOYSA-N nitryl fluoride Chemical compound [O-][N+](F)=O JVJQPDTXIALXOG-UHFFFAOYSA-N 0.000 claims description 2
244000005700 microbiome Species 0.000 claims 10
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
239000013543 active substance Substances 0.000 description 41
241000196324 Embryophyta Species 0.000 description 35
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 17
239000000126 substance Substances 0.000 description 16
239000000725 suspension Substances 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
238000012360 testing method Methods 0.000 description 14
239000002689 soil Substances 0.000 description 12
239000007921 spray Substances 0.000 description 11
239000004563 wettable powder Substances 0.000 description 11
238000011534 incubation Methods 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
239000002904 solvent Substances 0.000 description 9
240000007594 Oryza sativa Species 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
238000004519 manufacturing process Methods 0.000 description 8
239000000243 solution Substances 0.000 description 8
PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 7
239000013078 crystal Substances 0.000 description 7
230000001681 protective effect Effects 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
239000005995 Aluminium silicate Substances 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
235000012211 aluminium silicate Nutrition 0.000 description 6
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
208000015181 infectious disease Diseases 0.000 description 6
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 6
230000009885 systemic effect Effects 0.000 description 6
239000002253 acid Substances 0.000 description 5
239000008187 granular material Substances 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
206010061217 Infestation Diseases 0.000 description 4
208000031888 Mycoses Diseases 0.000 description 4
235000019993 champagne Nutrition 0.000 description 4
230000001338 necrotic effect Effects 0.000 description 4
239000000047 product Substances 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
240000004160 Capsicum annuum Species 0.000 description 3
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
-1 Cl-C4-alkyl Chemical group 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
244000098338 Triticum aestivum Species 0.000 description 3
240000006365 Vitis vinifera Species 0.000 description 3
235000014787 Vitis vinifera Nutrition 0.000 description 3
241000589652 Xanthomonas oryzae Species 0.000 description 3
241000567019 Xanthomonas vesicatoria Species 0.000 description 3
239000000654 additive Substances 0.000 description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
239000002585 base Substances 0.000 description 3
239000000969 carrier Substances 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
239000000428 dust Substances 0.000 description 3
235000013399 edible fruits Nutrition 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
230000000855 fungicidal effect Effects 0.000 description 3
239000000843 powder Substances 0.000 description 3
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 3
235000012239 silicon dioxide Nutrition 0.000 description 3
SRAWNDFHGTVUNZ-UHFFFAOYSA-M sodium;3,6-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(CCCC)=CC2=CC(CCCC)=CC=C21 SRAWNDFHGTVUNZ-UHFFFAOYSA-M 0.000 description 3
238000003756 stirring Methods 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 2
PJYDBLHGPLPWEJ-UHFFFAOYSA-N 2,3-dichloro-7-hydroxy-4-methylinden-1-one Chemical compound CC1=CC=C(O)C2=C1C(Cl)=C(Cl)C2=O PJYDBLHGPLPWEJ-UHFFFAOYSA-N 0.000 description 2
ZUNXGXNCUHCRBN-UHFFFAOYSA-N 4-bromo-2,3-dichloro-7-hydroxyinden-1-one Chemical compound OC1=CC=C(Br)C2=C1C(=O)C(Cl)=C2Cl ZUNXGXNCUHCRBN-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
CBQYNPHHHJTCJS-UHFFFAOYSA-N Alline Chemical compound C1=CC=C2C3(O)CCN(C)C3NC2=C1 CBQYNPHHHJTCJS-UHFFFAOYSA-N 0.000 description 2
244000105624 Arachis hypogaea Species 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
238000005727 Friedel-Crafts reaction Methods 0.000 description 2
235000011430 Malus pumila Nutrition 0.000 description 2
244000070406 Malus silvestris Species 0.000 description 2
235000015103 Malus silvestris Nutrition 0.000 description 2
241000315044 Passalora arachidicola Species 0.000 description 2
241001281803 Plasmopara viticola Species 0.000 description 2
241000221300 Puccinia Species 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
206010037888 Rash pustular Diseases 0.000 description 2
241000722133 Tilletia Species 0.000 description 2
241000722093 Tilletia caries Species 0.000 description 2
230000000844 anti-bacterial effect Effects 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
235000013339 cereals Nutrition 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
238000000576 coating method Methods 0.000 description 2
239000000470 constituent Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
238000005520 cutting process Methods 0.000 description 2
238000011161 development Methods 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
235000021186 dishes Nutrition 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000009472 formulation Methods 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
239000005457 ice water Substances 0.000 description 2
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
239000012948 isocyanate Substances 0.000 description 2
150000002513 isocyanates Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
229920000151 polyglycol Polymers 0.000 description 2
239000010695 polyglycol Substances 0.000 description 2
208000029561 pustule Diseases 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000005507 spraying Methods 0.000 description 2
208000024891 symptom Diseases 0.000 description 2
239000000454 talc Substances 0.000 description 2
235000012222 talc Nutrition 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
229940086542 triethylamine Drugs 0.000 description 2
238000009736 wetting Methods 0.000 description 2
239000008096 xylene Substances 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
HWPORWYITJLGGR-UHFFFAOYSA-N (1,2-dichloro-7-methyl-3-oxoinden-4-yl) n-methylcarbamate Chemical compound CNC(=O)OC1=CC=C(C)C2=C1C(=O)C(Cl)=C2Cl HWPORWYITJLGGR-UHFFFAOYSA-N 0.000 description 1
WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
FWCHKLDXJAPYFR-UHFFFAOYSA-N (7-bromo-1,2-dichloro-3-oxoinden-4-yl) methyl carbonate Chemical compound COC(=O)OC1=CC=C(Br)C2=C1C(=O)C(Cl)=C2Cl FWCHKLDXJAPYFR-UHFFFAOYSA-N 0.000 description 1
RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
MXMMPZIAUQYJFT-UHFFFAOYSA-N 2,3-dichloro-7-hydroxy-4-methyl-6-nitroinden-1-one Chemical compound CC1=CC([N+]([O-])=O)=C(O)C2=C1C(Cl)=C(Cl)C2=O MXMMPZIAUQYJFT-UHFFFAOYSA-N 0.000 description 1
SHHKCBRYZSVDIV-UHFFFAOYSA-N 2,3-dichloro-7-hydroxyinden-1-one Chemical class OC1=CC=CC2=C1C(=O)C(Cl)=C2Cl SHHKCBRYZSVDIV-UHFFFAOYSA-N 0.000 description 1
MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical class COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
QJPJQTDYNZXKQF-UHFFFAOYSA-N 4-bromoanisole Chemical compound COC1=CC=C(Br)C=C1 QJPJQTDYNZXKQF-UHFFFAOYSA-N 0.000 description 1
UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
235000003276 Apios tuberosa Nutrition 0.000 description 1
235000010777 Arachis hypogaea Nutrition 0.000 description 1
235000010744 Arachis villosulicarpa Nutrition 0.000 description 1
241000235349 Ascomycota Species 0.000 description 1
235000000832 Ayote Nutrition 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
241000221198 Basidiomycota Species 0.000 description 1
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
241001465180 Botrytis Species 0.000 description 1
238000006418 Brown reaction Methods 0.000 description 1
102100038916 Caspase-5 Human genes 0.000 description 1
241001157813 Cercospora Species 0.000 description 1
241000219112 Cucumis Species 0.000 description 1
235000015510 Cucumis melo subsp melo Nutrition 0.000 description 1
240000008067 Cucumis sativus Species 0.000 description 1
235000009849 Cucumis sativus Nutrition 0.000 description 1
241000219122 Cucurbita Species 0.000 description 1
235000009854 Cucurbita moschata Nutrition 0.000 description 1
235000009804 Cucurbita pepo subsp pepo Nutrition 0.000 description 1
241000219104 Cucurbitaceae Species 0.000 description 1
241000371644 Curvularia ravenelii Species 0.000 description 1
241000588698 Erwinia Species 0.000 description 1
241000223218 Fusarium Species 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
244000043261 Hevea brasiliensis Species 0.000 description 1
101100112336 Homo sapiens CASP5 gene Proteins 0.000 description 1
244000025221 Humulus lupulus Species 0.000 description 1
235000008694 Humulus lupulus Nutrition 0.000 description 1
239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
101100273286 Mus musculus Casp4 gene Proteins 0.000 description 1
240000005561 Musa balbisiana Species 0.000 description 1
244000061176 Nicotiana tabacum Species 0.000 description 1
235000002637 Nicotiana tabacum Nutrition 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241000233654 Oomycetes Species 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
101100335018 Pectobacterium carotovorum subsp. carotovorum fliQ gene Proteins 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
241000589516 Pseudomonas Species 0.000 description 1
241000221301 Puccinia graminis Species 0.000 description 1
241000221535 Pucciniales Species 0.000 description 1
206010039509 Scab Diseases 0.000 description 1
241000208292 Solanaceae 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
235000021536 Sugar beet Nutrition 0.000 description 1
244000299461 Theobroma cacao Species 0.000 description 1
235000009470 Theobroma cacao Nutrition 0.000 description 1
229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
235000021307 Triticum Nutrition 0.000 description 1
241000317942 Venturia <ichneumonid wasp> Species 0.000 description 1
241000228452 Venturia inaequalis Species 0.000 description 1
240000006677 Vicia faba Species 0.000 description 1
241000589634 Xanthomonas Species 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
230000000895 acaricidal effect Effects 0.000 description 1
239000000642 acaricide Substances 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
239000004411 aluminium Substances 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229940115440 aluminum sodium silicate Drugs 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical class COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
238000007080 aromatic substitution reaction Methods 0.000 description 1
239000003899 bactericide agent Substances 0.000 description 1
235000021015 bananas Nutrition 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
RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000007931 coated granule Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
150000001983 dialkylethers Chemical class 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
239000004491 dispersible concentrate Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000010410 dusting Methods 0.000 description 1
239000004495 emulsifiable concentrate Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
SNWQUNCRDLUDEX-UHFFFAOYSA-N inden-1-one Chemical class C1=CC=C2C(=O)C=CC2=C1 SNWQUNCRDLUDEX-UHFFFAOYSA-N 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
235000009973 maize Nutrition 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
229940124561 microbicide Drugs 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000017074 necrotic cell death Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
238000012856 packing Methods 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
229940044654 phenolsulfonic acid Drugs 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
235000012015 potatoes Nutrition 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000015136 pumpkin Nutrition 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000429 sodium aluminium silicate Substances 0.000 description 1
235000012217 sodium aluminium silicate Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
238000009331 sowing Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
125000001424 substituent group Chemical class 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Landscapes

Agricultural Chemicals And Associated Chemicals (AREA)

CA000402107A 1978-11-06 1982-04-30 Derives de trichlorovinyl-cetones, microbicides Expired CA1146596A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000402107A CA1146596A (fr)	1978-11-06	1982-04-30	Derives de trichlorovinyl-cetones, microbicides

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
CH11528/78-2		1978-11-06
CH1152878		1978-11-06
CA000339094A CA1140568A (fr)	1978-11-06	1979-11-02	Procedes d'obtention de derives de 1h-inden-1-ones, et emploi comme agents antimicrobiens dans certains produits
CA000402107A CA1146596A (fr)	1978-11-06	1982-04-30	Derives de trichlorovinyl-cetones, microbicides

Publications (1)

Publication Number	Publication Date
CA1146596A true CA1146596A (fr)	1983-05-17

Family

ID=27166477

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000402107A Expired CA1146596A (fr)	1978-11-06	1982-04-30	Derives de trichlorovinyl-cetones, microbicides

Country Status (1)

Country	Link
CA (1)	CA1146596A (fr)

1982
- 1982-04-30 CA CA000402107A patent/CA1146596A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2000-05-17	MKEX	Expiry

Publication	Publication Date	Title
US4785002A (en)	1988-11-15	Imidazo-pyrrolo-pyridines useful as fungicidal and growth-regulating agents
JPS6254103B2 (fr)	1987-11-13
JPS6128668B2 (fr)	1986-07-01
KR840001771B1 (ko)	1984-10-19	1-하이드록시에틸-아졸 유도체의 제조방법
KR840002291B1 (ko)	1984-12-15	N-알킬-n-아실아릴아민유도체의 제조방법
CA1197855A (fr)	1985-12-10	Derives de l'homoserine, procede de production utilisation comme microbicides
US4623377A (en)	1986-11-18	1,2,3,4-tetrahydroquinolin-1-ylcarbonylimidazoles and herbicidal use thereof
JPS6337788B2 (fr)	1988-07-27
US4459152A (en)	1984-07-10	Nitroarylalkylsulfone derivatives as plant growth stimulants
CA1134838A (fr)	1982-11-02	Derives d'acylaniline, utiles comme pesticides
US4322442A (en)	1982-03-30	Combating fungi with 1-halo-1-propyn-3-ols
CA1132583A (fr)	1982-09-28	Imides de l'acide cyclobutanedicarboxylique, procedes pour les fabriquer, et leur utilisation comme fongicides
CA1185246A (fr)	1985-04-09	CYCLOALKYL (.alpha.-TRIAZOLYL-.beta.-HYDROXY)-CETONES; PREPARATION ET EMPLOI COMME FONGICIDES ET REGULATEURS DE CROISSANCE POUR LES PLANTES
CA1167039A (fr)	1984-05-08	Ethers benzylpyrimidinylalkyliques; methode de preparation et utilisation comme regulateurs de la croissance des plantes et comme fongicides; produits intermediaires et leur preparation
CS212338B2 (en)	1982-03-26	Means for regulation of the plant growth and fungicide means and method of making the active substance
GB2035315A (en)	1980-06-18	Azolyl ketals, process for producing them, and their use as microbicides
US4291061A (en)	1981-09-22	1H-inden-1-one derivatives, processes for producing them, their use in microbicidal compositions, and for combating microorganisms
US4594353A (en)	1986-06-10	Azolyl-furan-derivatives having fungicide activity
US4416889A (en)	1983-11-22	Combating fungi with N-allenyl-acetanilides
IE44343B1 (en)	1981-10-21	Acylated imidazolyl-o,n-acetals,process for their preparation and their use as fungicides
US4181732A (en)	1980-01-01	1-Branched-alkylcarbonyl-3-(3,5-dihalophenyl)imidazolidine-2,4-diones
US4546109A (en)	1985-10-08	Organotin compounds and pesticidal compositions
US4397869A (en)	1983-08-09	Combating fungi with N-sulphenylated ureas
US4622064A (en)	1986-11-11	Triazolo-(3,2-c)perhydroxazin-8-one derivatives and use as fungicides and plant growth regulators
US4255437A (en)	1981-03-10	Combating fungi with 2-aryl-5-alkyl-3,4-dioxo-1,2,5-thiazolidine-1-oxides