CA1059141A - Microbicidal agents - Google Patents
Microbicidal agentsInfo
- Publication number
- CA1059141A CA1059141A CA223,937A CA223937A CA1059141A CA 1059141 A CA1059141 A CA 1059141A CA 223937 A CA223937 A CA 223937A CA 1059141 A CA1059141 A CA 1059141A
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- formula
- ethyl
- carbon atoms
- compounds
- 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.)
- Expired
Links
- 239000002855 microbicide agent Substances 0.000 title 1
- 241000233866 Fungi Species 0.000 claims abstract description 14
- 230000003032 phytopathogenic effect Effects 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 58
- 125000004432 carbon atom Chemical group C* 0.000 claims description 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 238000004519 manufacturing process Methods 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 15
- -1 halogen anion Chemical class 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 150000002431 hydrogen Chemical group 0.000 claims description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 238000001640 fractional crystallisation Methods 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 claims description 2
- QNAYBMKLOCPYGJ-UWTATZPHSA-N L-Alanine Natural products C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 claims description 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 2
- 230000010933 acylation Effects 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 229960003767 alanine Drugs 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 1
- ASLBBJLABBBEFO-UHFFFAOYSA-N methyl 2-(2,6-dimethyl-n-(2-phenylmethoxyacetyl)anilino)propanoate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)COCC1=CC=CC=C1 ASLBBJLABBBEFO-UHFFFAOYSA-N 0.000 claims 1
- UVKNAWCYNNYTGE-UHFFFAOYSA-N methyl 2-(2,6-dimethyl-n-(2-propan-2-yloxyacetyl)anilino)propanoate Chemical compound CC(C)OCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C UVKNAWCYNNYTGE-UHFFFAOYSA-N 0.000 claims 1
- GKYDMXVUQZNVMF-UHFFFAOYSA-N methyl 2-(2-chloro-6-methyl-n-(2-propan-2-yloxyacetyl)anilino)propanoate Chemical compound CC(C)OCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1Cl GKYDMXVUQZNVMF-UHFFFAOYSA-N 0.000 claims 1
- CWINJMFXMJHNIA-UHFFFAOYSA-N methyl 2-(2-ethyl-6-methyl-n-(2-propan-2-yloxyacetyl)anilino)propanoate Chemical compound CCC1=CC=CC(C)=C1N(C(C)C(=O)OC)C(=O)COC(C)C CWINJMFXMJHNIA-UHFFFAOYSA-N 0.000 claims 1
- LCSSVPBAIUUKSK-UHFFFAOYSA-N methyl 2-(n-(2-ethoxyacetyl)-2,3,6-trimethylanilino)propanoate Chemical compound CCOCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC(C)=C1C LCSSVPBAIUUKSK-UHFFFAOYSA-N 0.000 claims 1
- OXVYUWXEGXXFRO-UHFFFAOYSA-N methyl 2-(n-(2-ethoxyacetyl)-2,6-dimethylanilino)propanoate Chemical compound CCOCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C OXVYUWXEGXXFRO-UHFFFAOYSA-N 0.000 claims 1
- JFVZYTNGPKQTJH-UHFFFAOYSA-N methyl 2-(n-(2-methoxyacetyl)-2,3,6-trimethylanilino)propanoate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC(C)=C1C JFVZYTNGPKQTJH-UHFFFAOYSA-N 0.000 claims 1
- FGCBGECEUHIXKM-UHFFFAOYSA-N methyl 2-(n-(2-methoxyacetyl)-2,4,6-trimethylanilino)propanoate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=C(C)C=C1C FGCBGECEUHIXKM-UHFFFAOYSA-N 0.000 claims 1
- ZQEIXNIJLIKNTD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-UHFFFAOYSA-N 0.000 claims 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims 1
- 230000003641 microbiacidal effect Effects 0.000 abstract description 5
- 229940124561 microbicide Drugs 0.000 abstract description 2
- 235000013350 formula milk Nutrition 0.000 description 47
- 239000013543 active substance Substances 0.000 description 40
- 241000196324 Embryophyta Species 0.000 description 26
- 239000000203 mixture Substances 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000002689 soil Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000843 powder Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 208000031888 Mycoses Diseases 0.000 description 7
- 230000003287 optical effect Effects 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000005995 Aluminium silicate Substances 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 240000003768 Solanum lycopersicum Species 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 235000012211 aluminium silicate Nutrition 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
- 239000004563 wettable powder Substances 0.000 description 6
- 235000013339 cereals Nutrition 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 241000209219 Hordeum Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 235000019993 champagne Nutrition 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 238000005520 cutting process Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 3
- 241000233622 Phytophthora infestans Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 235000021536 Sugar beet Nutrition 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000370 acceptor Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 235000013399 edible fruits Nutrition 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 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
- 238000005507 spraying Methods 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 235000004535 Avena sterilis Nutrition 0.000 description 2
- 241001647031 Avena sterilis Species 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 240000008067 Cucumis sativus Species 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- 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 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 241001281803 Plasmopara viticola Species 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 241000233639 Pythium Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229940074995 bromine Drugs 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 235000015071 dressings Nutrition 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 230000009036 growth inhibition Effects 0.000 description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229920005610 lignin Polymers 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- ACEONLNNWKIPTM-UHFFFAOYSA-N methyl 2-bromopropanoate Chemical compound COC(=O)C(C)Br ACEONLNNWKIPTM-UHFFFAOYSA-N 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
- 229910052757 nitrogen Inorganic materials 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
- 230000008635 plant growth Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000003449 preventive effect Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 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
- 239000008096 xylene Substances 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
- CDFPXALLOJLBDX-UHFFFAOYSA-N 2,3-dibutylnaphthalene-1-sulfonic acid;sodium Chemical compound [Na].C1=CC=C2C(S(O)(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 CDFPXALLOJLBDX-UHFFFAOYSA-N 0.000 description 1
- GSFSVEDCYBDIGW-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-6-chlorophenol Chemical compound OC1=C(Cl)C=CC=C1C1=NC2=CC=CC=C2S1 GSFSVEDCYBDIGW-UHFFFAOYSA-N 0.000 description 1
- VVCMGAUPZIKYTH-VGHSCWAPSA-N 2-acetyloxybenzoic acid;[(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;1,3,7-trimethylpurine-2,6-dione Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VVCMGAUPZIKYTH-VGHSCWAPSA-N 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- FPQQSNUTBWFFLB-UHFFFAOYSA-N 2-chloro-n-(2,6-dimethylphenyl)acetamide Chemical compound CC1=CC=CC(C)=C1NC(=O)CCl FPQQSNUTBWFFLB-UHFFFAOYSA-N 0.000 description 1
- IULJSGIJJZZUMF-UHFFFAOYSA-N 2-hydroxybenzenesulfonic acid Chemical compound OC1=CC=CC=C1S(O)(=O)=O IULJSGIJJZZUMF-UHFFFAOYSA-N 0.000 description 1
- JJKWHOSQTYYFAE-UHFFFAOYSA-N 2-methoxyacetyl chloride Chemical compound COCC(Cl)=O JJKWHOSQTYYFAE-UHFFFAOYSA-N 0.000 description 1
- FUCUHFQBEBZAFY-UHFFFAOYSA-N 6-ethyl-2,3-dimethylaniline Chemical compound CCC1=CC=C(C)C(C)=C1N FUCUHFQBEBZAFY-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000221198 Basidiomycota Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- 241000219112 Cucumis Species 0.000 description 1
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- 241000219122 Cucurbita Species 0.000 description 1
- 235000009804 Cucurbita pepo subsp pepo Nutrition 0.000 description 1
- NPOJQCVWMSKXDN-UHFFFAOYSA-N Dacthal Chemical compound COC(=O)C1=C(Cl)C(Cl)=C(C(=O)OC)C(Cl)=C1Cl NPOJQCVWMSKXDN-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 241001480059 Erysiphaceae Species 0.000 description 1
- 241000508723 Festuca rubra Species 0.000 description 1
- 244000286663 Ficus elastica Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 235000008694 Humulus lupulus Nutrition 0.000 description 1
- 240000004296 Lolium perenne Species 0.000 description 1
- 240000008790 Musa x paradisiaca Species 0.000 description 1
- 235000018290 Musa x paradisiaca Nutrition 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 241000233654 Oomycetes Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241001223281 Peronospora Species 0.000 description 1
- 241000233614 Phytophthora Species 0.000 description 1
- 241000233626 Plasmopara Species 0.000 description 1
- 241000209049 Poa pratensis Species 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 241001281802 Pseudoperonospora Species 0.000 description 1
- 241000221535 Pucciniales Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 241000208292 Solanaceae Species 0.000 description 1
- 235000002560 Solanum lycopersicum Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- 241000358324 Viverricula indica 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
- 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
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229940115440 aluminum sodium silicate Drugs 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000001723 carbon free-radicals Chemical class 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000007931 coated granule Substances 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229920001577 copolymer Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 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
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000008121 plant development Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000000429 sodium aluminium silicate Substances 0.000 description 1
- 235000012217 sodium aluminium silicate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- 244000045561 useful plants Species 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
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/30—Isothioureas
- C07C335/32—Isothioureas having sulfur atoms of isothiourea groups bound to acyclic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH499574A CH592410A5 (en) | 1974-04-09 | 1974-04-09 | n-Substd. acetanilides - microbicides useful for treating phytopathogenic fungi, prepd. by acylation of substd. anilines |
| CH325975A CH608690A5 (en) | 1975-03-14 | 1975-03-14 | Microbicidal composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1059141A true CA1059141A (en) | 1979-07-24 |
Family
ID=25692584
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA223,937A Expired CA1059141A (en) | 1974-04-09 | 1975-04-07 | Microbicidal agents |
Country Status (33)
Families Citing this family (82)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| OA04979A (fr) | 1974-04-09 | 1980-11-30 | Ciba Geigy | Nouveaux dérivés de l'aniline utiles comme agents microbicides et leur procédé de préparation. |
| US4147792A (en) * | 1977-02-04 | 1979-04-03 | Ciba-Geigy Corporation | Fungicidal compositions |
| CH627343A5 (en) * | 1977-03-28 | 1982-01-15 | Ciba Geigy Ag | Microbicide |
| CH629939A5 (de) * | 1977-03-29 | 1982-05-28 | Ciba Geigy Ag | Mikrobizides mittel. |
| AT368358B (de) * | 1977-12-24 | 1982-10-11 | Fisons Ltd | Schaedlingsbekaempfungs- und pflanzenwachstumsregulierungsmittel |
| DE2802211A1 (de) | 1978-01-19 | 1979-07-26 | Basf Ag | N-substituierte 2,6-dialkylaniline und verfahren zur herstellung von n- substituierten 2,6-dialkylanilinen |
| BG28977A3 (en) | 1978-02-02 | 1980-08-15 | Montedison Spa | Fungicide means and method for fungus fighting |
| CS217978B2 (en) * | 1978-04-01 | 1983-02-25 | Lilly Industries Ltd | Fungicide means |
| CH635313A5 (de) * | 1978-05-19 | 1983-03-31 | Ciba Geigy Ag | Pflanzenmikrobizid wirkende hydrazino-acetanilid-derivate, verfahren zu ihrer herstellung sowie mikrobizide mittel mit diesen praeparaten als wirkstoffe. |
| CH635819A5 (de) * | 1978-06-02 | 1983-04-29 | Ciba Geigy Ag | Alkoxy-alkoxy-acetyl acylalanine, deren herstellung und verwendung als pflanzenfungizide. |
| CH637368A5 (de) * | 1978-10-27 | 1983-07-29 | Ciba Geigy Ag | Anilinderivate und daraus hergestellte schaedlingsbekaempfungsmittel. |
| CH641760A5 (de) * | 1978-11-27 | 1984-03-15 | Ciba Geigy Ag | Schaedlingsbekaempfungsmittel. |
| CH639940A5 (en) * | 1978-12-05 | 1983-12-15 | Ciba Geigy Ag | Substituted N-alkoxycarbonylethyl-N-acylanilines, microbicides containing them, and process for the preparation of the compounds |
| DE2948734A1 (de) * | 1978-12-07 | 1980-06-19 | Ciba Geigy Ag | Schaedlingsbekaempfungsmittel |
| FR2447373A1 (fr) * | 1979-01-24 | 1980-08-22 | Rhone Poulenc Agrochimie | Produits derives de l'aniline ayant une activite antifongique ainsi que leur procede de preparation |
| FR2451914A1 (fr) * | 1979-03-20 | 1980-10-17 | Ciba Geigy Ag | Composes aromatiques azotes possedant des proprietes microbicides |
| CH639643A5 (en) * | 1979-03-21 | 1983-11-30 | Ciba Geigy Ag | Pesticides |
| MA18800A1 (fr) * | 1979-04-10 | 1980-12-31 | Ciba Geigy Ag | Naphtylamines acylees,procede pour leur preparation et leur application comme phytofongicides |
| DE2915026A1 (de) * | 1979-04-12 | 1980-10-30 | Bayer Ag | N,n-disubstituierte ethylglycin (thiol)ester, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
| DE2917914A1 (de) * | 1979-05-03 | 1980-11-13 | Ciba Geigy Ag | N-(alkoxy- bzw. alkoxycarbonylalkyl)- n-alkoxyalkoxyacetyl-anilin-derivate |
| DE2917893A1 (de) * | 1979-05-03 | 1980-11-13 | Ciba Geigy Ag | N-(alkoxy- bzw. alkoxycarbonalalkyl)- n-hydroxyacetyl- bzw. propionyl-anilin- derivate als pflanzenfungizide |
| ES8104796A1 (es) * | 1979-07-25 | 1981-05-16 | Hoechst Ag | Procedimiento para la preparacion de anilidas de acido tio- glicolico, fungicidas |
| ATE2426T1 (de) * | 1979-08-29 | 1983-03-15 | Ciba-Geigy Ag | Sulfinyl- und sulfonylacetanilide, verfahren zu deren herstellung und deren verwendung als mikrobizide. |
| MA19111A1 (fr) * | 1979-10-26 | 1981-12-31 | Ciba Geigy Ag | Derives de l'homoserine,procede pour leur preparation et leur utilisation en tant que microbicides |
| DE2946910A1 (de) * | 1979-11-21 | 1981-07-02 | Hoechst Ag, 6230 Frankfurt | Fungizide sulfonyl-, bzw. sulfinylacetanilide |
| US4377587A (en) * | 1980-07-25 | 1983-03-22 | Ciba-Geigy Corporation | Arylamine derivatives and use thereof as microbicides |
| MA19215A1 (fr) * | 1980-07-25 | 1982-04-01 | Ciba Geigy Ag | Nouveaux derives arylamines,procede pour leur fabrication et utilisation en tant que microbicides . |
| US4448773A (en) * | 1981-04-29 | 1984-05-15 | Ciba-Geigy Corporation | Microbicidal N-alkoxycarbonyl-alkyl-N-substituted acetyl-anilines and -naphthylamines |
| FR2505327A1 (fr) * | 1981-05-08 | 1982-11-12 | Rhone Poulenc Agrochimie | Procede d'halogenation en meta de n-(o,o'-dialkyl phenyl) alaninates et homologues |
| FR2513993A1 (fr) * | 1981-10-06 | 1983-04-08 | Rhone Poulenc Agrochimie | Nouveaux fongicides homologues des n-phenyl alaninates et leur procede de preparation et leur application |
| CH654979A5 (de) * | 1982-01-26 | 1986-03-27 | Sandoz Ag | Fungizide und ihre verwendung. |
| US4742079A (en) * | 1982-01-26 | 1988-05-03 | Sandoz Ltd. | Fungicides containing cymoxanil and metalaxyl |
| EP0230209A3 (de) * | 1985-12-16 | 1987-08-12 | Ciba-Geigy Ag | Mikrobizide |
| HU198825B (en) * | 1987-03-09 | 1989-12-28 | Chinoin Gyogyszer Es Vegyeszet | Synergic fungicides |
| HU202481B (en) * | 1989-04-19 | 1991-03-28 | Nitrokemia Ipartelepek | Process for producing n-phenyl-n-(methoxyacetyl)-dl-alanine methyl ester derivatives |
| CA2023176A1 (en) * | 1989-08-25 | 1991-02-26 | Margaret M. Bowers-Daines | Preparation and use of iodopropargyl esters of a-amino acid derivatives as antimicrobial agents |
| US5252745A (en) * | 1989-08-25 | 1993-10-12 | Rohm And Haas Company | Preparation and use of iodopropargyl esters of α-amino acid derivatives as antimicrobial agents |
| US5155136A (en) * | 1990-11-23 | 1992-10-13 | Eastman Kodak Company | Fungicidal, 2-acylacetanilide derivatives |
| US5266597A (en) * | 1990-11-23 | 1993-11-30 | Eastman Kodak Company | Fungicidal 2-acylacetanilide derivatives |
| US5723491A (en) * | 1994-07-11 | 1998-03-03 | Novartis Corporation | Fungicidal composition and method of controlling fungus infestation |
| CH687169A5 (de) | 1994-07-11 | 1996-10-15 | Ciba Geigy Ag | Mikrobizide. |
| DE4429014A1 (de) | 1994-08-16 | 1996-02-22 | Basf Ag | Verfahren zur Herstellung von cyclischen Aminen |
| RU2001101908A (ru) | 1998-06-17 | 2003-02-10 | Байер Акциенгезельшафт (De) | Средства для борьбы с вредителями растений |
| DE10049804A1 (de) * | 2000-10-09 | 2002-04-18 | Bayer Ag | Wirkstoffkombinationen mit fungiziden und akariziden Eigenschaften |
| DE10347090A1 (de) | 2003-10-10 | 2005-05-04 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| DE10349501A1 (de) | 2003-10-23 | 2005-05-25 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| EP2255630A3 (de) | 2004-04-30 | 2012-09-26 | Basf Se | Fungizide Mischungen |
| US20060264415A1 (en) * | 2005-04-01 | 2006-11-23 | Methylgene Inc. | Inhibitors of histone deacetylase |
| EA201270781A1 (ru) | 2005-06-09 | 2013-09-30 | Байер Кропсайенс Аг | Комбинации биологически активных веществ |
| DE102005026482A1 (de) | 2005-06-09 | 2006-12-14 | Bayer Cropscience Ag | Wirkstoffkombinationen |
| ITMI20051558A1 (it) | 2005-08-09 | 2007-02-10 | Isagro Spa | Miscele e-o composizioni sinergiche cin elevata attivita'fungicida |
| DE102006023263A1 (de) | 2006-05-18 | 2007-11-22 | Bayer Cropscience Ag | Synergistische Wirkstoffkombinationen |
| US20100041682A1 (en) | 2006-09-18 | 2010-02-18 | Langewald Juergen | Ternary Pesticidal Mixtures |
| EP2258177A3 (en) | 2006-12-15 | 2011-11-09 | Rohm and Haas Company | Mixtures comprising 1-methylcyclopropene |
| WO2008095924A2 (de) | 2007-02-06 | 2008-08-14 | Basf Se | Insektizide als safener für fungizide mit phytotoxischer wirkung |
| CL2008001181A1 (es) | 2007-04-23 | 2009-10-23 | Basf Se | Metodo para mejorar la salud de la planta y/o controlar plagas en plantas con al menos una modificacion transgenica relacionada con el aumento del rendimiento que consiste en la aplicacion de una composicion quimica que comprende al menos un ingrediente activo seleccionado de insecticidas, fungicidas o herbicidas. |
| EP2000028A1 (de) * | 2007-06-06 | 2008-12-10 | Bayer CropScience Aktiengesellschaft | Fungizide Wirkstoffkombinationen |
| EP2000030A1 (de) * | 2007-06-06 | 2008-12-10 | Bayer CropScience AG | Fungizide Wirkstoffkombinationen |
| JP2010540495A (ja) | 2007-09-26 | 2010-12-24 | ビーエーエスエフ ソシエタス・ヨーロピア | ボスカリド及びクロロタロニルを含む三成分殺菌組成物 |
| DE102007045920B4 (de) | 2007-09-26 | 2018-07-05 | Bayer Intellectual Property Gmbh | Synergistische Wirkstoffkombinationen |
| JP5417814B2 (ja) * | 2008-11-25 | 2014-02-19 | 住友化学株式会社 | 植物病害防除用組成物及び植物病害の防除方法 |
| BR112012001080A2 (pt) | 2009-07-16 | 2015-09-01 | Bayer Cropscience Ag | Combinações de substâncias ativas sinérgicas contendo feniltriazóis |
| WO2011026796A1 (en) | 2009-09-01 | 2011-03-10 | Basf Se | Synergistic fungicidal mixtures comprising lactylates and method for combating phytopathogenic fungi |
| EP2417853A1 (en) | 2010-08-05 | 2012-02-15 | Basf Se | Synergistic fungicidal and insecticidal mixtures comprising a fungicide and an insecticide |
| KR20130132942A (ko) | 2010-12-20 | 2013-12-05 | 바스프 에스이 | 피라졸 화합물을 포함하는 살충 활성 혼합물 |
| EP2481284A3 (en) | 2011-01-27 | 2012-10-17 | Basf Se | Pesticidal mixtures |
| WO2012127009A1 (en) | 2011-03-23 | 2012-09-27 | Basf Se | Compositions containing polymeric, ionic compounds comprising imidazolium groups |
| EP3295797A1 (en) | 2011-03-23 | 2018-03-21 | Bayer Intellectual Property GmbH | Active compound combinations |
| US20140200136A1 (en) | 2011-09-02 | 2014-07-17 | Basf Se | Agricultural mixtures comprising arylquinazolinone compounds |
| JP2013142063A (ja) * | 2012-01-10 | 2013-07-22 | Sumitomo Chemical Co Ltd | 植物病害防除組成物およびその用途 |
| 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 |
| JP6051799B2 (ja) * | 2012-11-12 | 2016-12-27 | 住友化学株式会社 | 農薬用組成物及び植物の生長を促進する方法 |
| JP6576829B2 (ja) | 2012-12-20 | 2019-09-18 | ビーエーエスエフ アグロ ベー．ブイ． | トリアゾール化合物を含む組成物 |
| EP2783569A1 (en) | 2013-03-28 | 2014-10-01 | Basf Se | Compositions comprising a triazole compound |
| EP2835052A1 (en) | 2013-08-07 | 2015-02-11 | Basf Se | Fungicidal mixtures comprising pyrimidine fungicides |
| WO2015036059A1 (en) | 2013-09-16 | 2015-03-19 | Basf Se | Fungicidal pyrimidine compounds |
| CN105722833A (zh) | 2013-09-16 | 2016-06-29 | 巴斯夫欧洲公司 | 杀真菌的嘧啶化合物 |
| EP2979549A1 (en) | 2014-07-31 | 2016-02-03 | Basf Se | Method for improving the health of a plant |
| EP2910126A1 (en) | 2015-05-05 | 2015-08-26 | Bayer CropScience AG | Active compound combinations having insecticidal properties |
| US20180184654A1 (en) | 2015-07-02 | 2018-07-05 | BASF Agro B.V. | Pesticidal Compositions Comprising a Triazole Compound |
| CA3003065A1 (en) | 2015-10-27 | 2017-05-04 | Bayer Cropscience Aktiengesellschaft | Composition comprising a safener, a fungicide and metalaxyl |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1164160A (en) * | 1966-12-30 | 1969-09-17 | Shell Int Research | N,N-Disubstituted Amino Acid Derivatives and their use as Herbicides |
| GB1289283A (cg-RX-API-DMAC7.html) * | 1970-03-04 | 1972-09-13 | ||
| DE2212268C3 (de) * | 1971-03-15 | 1979-09-13 | Sumitomo Chemical Co., Ltd., Osaka (Japan) | N-Halogenacetylanilinoessigsäureester, Verfahren zu deren Herstellung und diese enthaltende herbicide Massen |
| SE397191B (sv) * | 1972-10-13 | 1977-10-24 | Ciba Geigy Ag | N-(1'-alkoxikarbonyl-etyl)-n-haloacetyl-2,6-dialkylaniliner till anvendning som fungicid |
| US4151299A (en) | 1974-04-09 | 1979-04-24 | Ciba-Geigy Corporation | Certain aniline derivatives as microbicidal agents |
| US4204002A (en) * | 1974-04-09 | 1980-05-20 | Ciba-Geigy Corporation | Methods of using N-(substituted)-N-alkoxy carbonyl anilino compounds |
| OA04979A (fr) * | 1974-04-09 | 1980-11-30 | Ciba Geigy | Nouveaux dérivés de l'aniline utiles comme agents microbicides et leur procédé de préparation. |
| US4206228A (en) * | 1974-04-09 | 1980-06-03 | Ciba-Geigy Corporation | Microbicidal aniline derivatives |
| CH623458A5 (cg-RX-API-DMAC7.html) * | 1975-09-30 | 1981-06-15 | Ciba Geigy Ag |
-
1973
- 1973-04-08 OA OA55472A patent/OA04979A/xx unknown
-
1975
- 1975-03-26 FI FI750922A patent/FI61477C/fi not_active IP Right Cessation
- 1975-03-26 DK DK136375AA patent/DK142360B/da not_active IP Right Cessation
- 1975-03-26 NO NO751088A patent/NO144960C/no unknown
- 1975-03-26 SE SE7503519A patent/SE430015B/xx not_active IP Right Cessation
- 1975-04-07 FR FR7510722A patent/FR2267042B1/fr not_active Expired
- 1975-04-07 DE DE2515091A patent/DE2515091C2/de not_active Expired
- 1975-04-07 CA CA223,937A patent/CA1059141A/en not_active Expired
- 1975-04-07 PH PH17028A patent/PH13585A/en unknown
- 1975-04-07 LU LU72224A patent/LU72224A1/xx unknown
- 1975-04-07 HU HU75CI1567A patent/HU173318B/hu unknown
- 1975-04-08 IT IT22134/75A patent/IT1049536B/it active
- 1975-04-08 BG BG029586A patent/BG26357A3/xx unknown
- 1975-04-08 IL IL47046A patent/IL47046A/xx unknown
- 1975-04-08 IE IE787/75A patent/IE40913B1/xx unknown
- 1975-04-08 YU YU0893/75A patent/YU37311B/xx unknown
- 1975-04-08 CY CY1010A patent/CY1010A/xx unknown
- 1975-04-08 GB GB14380/75A patent/GB1500581A/en not_active Expired
- 1975-04-08 ES ES436385A patent/ES436385A1/es not_active Expired
- 1975-04-08 AT AT263875A patent/AT341827B/de not_active IP Right Cessation
- 1975-04-08 DD DD185303A patent/DD118979A5/xx unknown
- 1975-04-08 DD DD192564A patent/DD124973A5/xx unknown
- 1975-04-08 TR TR18846A patent/TR18846A/xx unknown
- 1975-04-09 NL NLAANVRAGE7504236,A patent/NL184781C/xx not_active IP Right Cessation
- 1975-04-09 RO RO106425A patent/RO84020B/ro unknown
- 1975-04-09 SU SU752124200A patent/SU730268A3/ru active
- 1975-04-09 PL PL1975192740A patent/PL104373B1/pl unknown
- 1975-04-09 CS CS752436A patent/CS187468B2/cs unknown
- 1975-04-09 RO RO7581942A patent/RO79678A/ro unknown
- 1975-04-09 RO RO106424A patent/RO83787B/ro unknown
- 1975-04-09 PL PL1975179458A patent/PL97724B1/pl unknown
- 1975-04-09 JP JP4314775A patent/JPS5443573B2/ja not_active Expired
-
1976
- 1976-07-01 SU SU762375578A patent/SU639445A3/ru active
-
1979
- 1979-04-08 AR AR258284A patent/AR226272A1/es active
- 1979-05-11 KE KE2960A patent/KE2960A/xx unknown
- 1979-06-21 HK HK403/79A patent/HK40379A/xx unknown
- 1979-12-07 US US06/101,355 patent/US4294850A/en not_active Expired - Lifetime
-
1980
- 1980-12-30 MY MY56/80A patent/MY8000056A/xx unknown
-
1981
- 1981-06-15 US US06/274,019 patent/US4427696A/en not_active Expired - Lifetime
- 1981-06-15 US US06/273,801 patent/US4439447A/en not_active Expired - Lifetime
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1059141A (en) | Microbicidal agents | |
| US4151299A (en) | Certain aniline derivatives as microbicidal agents | |
| CA1050546A (en) | Derivatives of n-carboxy-alkyl anilides | |
| CA1064952A (en) | Microbicidal compositions | |
| US4143155A (en) | Sulfonylglycolic anilide fungicides | |
| US4025648A (en) | Haloacylanilides and use as fungicides | |
| US4094990A (en) | Certain phytofungicidal n-furanyl carbonyl and tetrahydrofuranyl carbonyl, n-(substituted)phenyl alanines | |
| CA1073922A (en) | Microbicidal acylated thiopropionyl anilines | |
| PL97728B1 (pl) | Srodek mikrobojczy i regulujacy wzrost roslin | |
| CA1131239A (en) | Microbicides for controlling plant diseases | |
| HU188127B (en) | Plant fungicides containing acylated naphthylamine derivatives and process for preparing the active substances | |
| US4206228A (en) | Microbicidal aniline derivatives | |
| JPS648615B2 (cg-RX-API-DMAC7.html) | ||
| CA1121376A (en) | Microbicides | |
| US4330556A (en) | Microbicidal N-1'-hydrocarbyloxycarbonylethyl)-N-alkoxyacetylanilines | |
| US4101672A (en) | Microbicidal alanine thioesters | |
| CA1127178A (en) | Microbicidal composition | |
| US4214005A (en) | Fungicidal alkoxyalkoxyacetyl acylalanines | |
| CA1065332A (en) | Acylated phenylamino thiopropionates | |
| US4224337A (en) | Pesticidal compositions | |
| CH639643A5 (en) | Pesticides | |
| US3992387A (en) | Octahydropyrindine phosphorylacylamines | |
| US4165381A (en) | Microbicidal compositions | |
| SI7510893A8 (sl) | Postopek za pripravo novih anilinov | |
| CH608690A5 (en) | Microbicidal composition |