DK141118B - Fungicide halogenacetanilider til anvendelse ved plantebeskyttelse. - Google Patents
Fungicide halogenacetanilider til anvendelse ved plantebeskyttelse. Download PDFInfo
- Publication number
- DK141118B DK141118B DK136075AA DK136075A DK141118B DK 141118 B DK141118 B DK 141118B DK 136075A A DK136075A A DK 136075AA DK 136075 A DK136075 A DK 136075A DK 141118 B DK141118 B DK 141118B
- Authority
- DK
- Denmark
- Prior art keywords
- soil
- plants
- formula
- parts
- sugar beet
- Prior art date
Links
- 230000000855 fungicidal effect Effects 0.000 title claims description 7
- -1 halogen acetanilides Chemical class 0.000 title description 14
- 229910052736 halogen Inorganic materials 0.000 title description 6
- 239000000417 fungicide Substances 0.000 title description 3
- 241000196324 Embryophyta Species 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 28
- 239000013543 active substance Substances 0.000 claims description 25
- 230000000694 effects Effects 0.000 claims description 18
- 241000233866 Fungi Species 0.000 claims description 14
- 239000007921 spray Substances 0.000 claims description 14
- 239000000843 powder Substances 0.000 claims description 13
- 239000002689 soil Substances 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 claims description 6
- 238000002474 experimental method Methods 0.000 claims description 6
- 235000021536 Sugar beet Nutrition 0.000 claims description 4
- 238000005507 spraying Methods 0.000 claims description 4
- 238000009472 formulation Methods 0.000 claims description 2
- 239000004576 sand Substances 0.000 claims 2
- 241000335053 Beta vulgaris Species 0.000 claims 1
- 235000021533 Beta vulgaris Nutrition 0.000 claims 1
- 239000007900 aqueous suspension Substances 0.000 claims 1
- 230000002969 morbid Effects 0.000 claims 1
- 238000005554 pickling Methods 0.000 claims 1
- 238000009331 sowing Methods 0.000 claims 1
- 239000000460 chlorine Substances 0.000 description 56
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 11
- 229910052801 chlorine Inorganic materials 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 239000005995 Aluminium silicate Substances 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 235000012211 aluminium silicate Nutrition 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000008187 granular material Substances 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
- 239000000243 solution Substances 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 230000003032 phytopathogenic effect Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 240000003768 Solanum lycopersicum Species 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 235000019993 champagne Nutrition 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 239000011630 iodine Chemical group 0.000 description 4
- 229910052740 iodine Chemical group 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000002904 solvent Substances 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
- 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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 235000013339 cereals Nutrition 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000005520 cutting process Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 235000013399 edible fruits Nutrition 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 239000004009 herbicide Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- WXBUNMRUBVTEKD-UHFFFAOYSA-N methyl 2-(2-chloro-6-methylanilino)propanoate Chemical compound COC(=O)C(C)NC1=C(C)C=CC=C1Cl WXBUNMRUBVTEKD-UHFFFAOYSA-N 0.000 description 3
- ACEONLNNWKIPTM-UHFFFAOYSA-N methyl 2-bromopropanoate Chemical compound COC(=O)C(C)Br ACEONLNNWKIPTM-UHFFFAOYSA-N 0.000 description 3
- 230000003641 microbiacidal effect Effects 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 240000008067 Cucumis sativus Species 0.000 description 2
- 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
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- 241001281803 Plasmopara viticola Species 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 229960003767 alanine Drugs 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229920005610 lignin Polymers 0.000 description 2
- OMUMQXQJPMKSOD-UHFFFAOYSA-N methyl 2-(2,6-dichloroanilino)propanoate Chemical compound COC(=O)C(C)NC1=C(Cl)C=CC=C1Cl OMUMQXQJPMKSOD-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
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 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
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 230000003449 preventive effect Effects 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 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 2
- 239000007787 solid Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- PNVPNXKRAUBJGW-UHFFFAOYSA-N (2-chloroacetyl) 2-chloroacetate Chemical compound ClCC(=O)OC(=O)CCl PNVPNXKRAUBJGW-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
- 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
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- JDMFXJULNGEPOI-UHFFFAOYSA-N 2,6-dichloroaniline Chemical compound NC1=C(Cl)C=CC=C1Cl JDMFXJULNGEPOI-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
- WFNLHDJJZSJARK-UHFFFAOYSA-N 2-chloro-6-methylaniline Chemical compound CC1=CC=CC(Cl)=C1N WFNLHDJJZSJARK-UHFFFAOYSA-N 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000000832 Ayote Nutrition 0.000 description 1
- 241000221198 Basidiomycota Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000219112 Cucumis Species 0.000 description 1
- 235000015510 Cucumis melo subsp melo Nutrition 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
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 235000008694 Humulus lupulus Nutrition 0.000 description 1
- 244000025221 Humulus lupulus Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- QNAYBMKLOCPYGJ-UWTATZPHSA-N L-Alanine Natural products C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 description 1
- 240000008790 Musa x paradisiaca Species 0.000 description 1
- 235000018290 Musa x paradisiaca Nutrition 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- NPKSPKHJBVJUKB-UHFFFAOYSA-N N-phenylglycine Chemical class OC(=O)CNC1=CC=CC=C1 NPKSPKHJBVJUKB-UHFFFAOYSA-N 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 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
- 241000233622 Phytophthora infestans Species 0.000 description 1
- 241000233626 Plasmopara Species 0.000 description 1
- 241001281802 Pseudoperonospora Species 0.000 description 1
- 241000221535 Pucciniales Species 0.000 description 1
- 241000233639 Pythium Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 244000273928 Zingiber officinale Species 0.000 description 1
- 235000006886 Zingiber officinale Nutrition 0.000 description 1
- ZXKIFUWANBZSKF-UHFFFAOYSA-N [I].CC(O)=O Chemical compound [I].CC(O)=O ZXKIFUWANBZSKF-UHFFFAOYSA-N 0.000 description 1
- 150000001243 acetic acids Chemical class 0.000 description 1
- 239000012345 acetylating agent Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- DNEHKUCSURWDGO-UHFFFAOYSA-N aluminum sodium Chemical compound [Na].[Al] DNEHKUCSURWDGO-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 239000000022 bacteriostatic agent Substances 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 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
- 230000000052 comparative effect Effects 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 1
- 239000002038 ethyl acetate fraction Substances 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- ZBHDTYQJAQDBIH-UHFFFAOYSA-N fluoroacetyl chloride Chemical compound FCC(Cl)=O ZBHDTYQJAQDBIH-UHFFFAOYSA-N 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 230000001408 fungistatic effect Effects 0.000 description 1
- 235000008397 ginger Nutrition 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000002363 herbicidal effect Effects 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
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940124561 microbicide Drugs 0.000 description 1
- 239000002855 microbicide agent Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000003750 molluscacide Substances 0.000 description 1
- 230000002013 molluscicidal effect Effects 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 230000001737 promoting effect Effects 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
- 238000012958 reprocessing Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000003128 rodenticide Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 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
- 239000004334 sorbic acid Substances 0.000 description 1
- 238000006277 sulfonation 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
- 230000008719 thickening Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 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
- 238000009941 weaving Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 235000014101 wine Nutrition 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH451074A CH590607A5 (en) | 1974-04-01 | 1974-04-01 | N-Aryl-N-haloacetyl-alanine methyl esters - prepd. by haloacetylation of N-aryl-alanine methyl esters |
| CH451074 | 1974-04-01 | ||
| CH1152274 | 1974-08-23 | ||
| CH1152174A CH595755A5 (en) | 1974-08-23 | 1974-08-23 | N-Aryl-N-haloacetyl-alanine methyl esters |
| CH1152274A CH595756A5 (en) | 1974-08-23 | 1974-08-23 | N-Aryl-N-haloacetyl-alanine methyl esters |
| CH1152174 | 1974-08-23 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK136075A DK136075A (fr) | 1975-10-02 |
| DK141118B true DK141118B (da) | 1980-01-21 |
| DK141118C DK141118C (fr) | 1980-06-30 |
Family
ID=27174877
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK136075AA DK141118B (da) | 1974-04-01 | 1975-03-26 | Fungicide halogenacetanilider til anvendelse ved plantebeskyttelse. |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4032657A (fr) |
| JP (1) | JPS5910321B2 (fr) |
| AR (1) | AR209297A1 (fr) |
| AT (1) | AT343406B (fr) |
| BG (1) | BG26508A3 (fr) |
| CS (1) | CS183787B2 (fr) |
| DD (1) | DD118788A5 (fr) |
| DE (1) | DE2513730C2 (fr) |
| DK (1) | DK141118B (fr) |
| EG (1) | EG12082A (fr) |
| ES (1) | ES436153A1 (fr) |
| FI (1) | FI61476C (fr) |
| FR (1) | FR2265726B1 (fr) |
| GB (1) | GB1495348A (fr) |
| HU (1) | HU173316B (fr) |
| IE (1) | IE41102B1 (fr) |
| IL (1) | IL46968A (fr) |
| LU (1) | LU72173A1 (fr) |
| NL (1) | NL7503758A (fr) |
| NO (1) | NO144962C (fr) |
| OA (1) | OA04917A (fr) |
| PH (1) | PH11591A (fr) |
| RO (1) | RO70589A (fr) |
| SE (1) | SE411450B (fr) |
| SU (1) | SU692535A3 (fr) |
| TR (1) | TR18662A (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK150848B (da) * | 1976-09-17 | 1987-07-06 | Ciba Geigy | N-substituerede sulfonylglycolsyreanilider med fungicid virkning mod fytopatogene svampe samt anvendelse deraf til bekaempelse af fytopatogene svampe |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2648074A1 (de) * | 1976-10-23 | 1978-04-27 | Bayer Ag | N-chloracetyl-n-phenyl-alaninester, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
| 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 |
| CH635819A5 (de) * | 1978-06-02 | 1983-04-29 | Ciba Geigy Ag | Alkoxy-alkoxy-acetyl acylalanine, deren herstellung und verwendung als pflanzenfungizide. |
| US4440780A (en) * | 1979-06-01 | 1984-04-03 | Chevron Research Company | Fungicidal 3-(N-acyl-N-arylamino)-and 3-(N-thionoacyl-N-arylamino)-gamma-butyrolactones and gamma-thiobutyrolactones |
| DE2913459A1 (de) * | 1979-04-04 | 1980-11-13 | Bayer Ag | N-dichloracetyl-n-phenyl-alanin (thiol)ester, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
| 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 |
| US4266071A (en) * | 1980-06-09 | 1981-05-05 | Ciba-Geigy Corporation | Process for the preparation of N-(1-alkoxycarbonylethyl)-2,6-dialkylanilines |
| US4267356A (en) * | 1980-06-09 | 1981-05-12 | Ciba-Geigy Corporation | Process for the preparation of N-(1'-alkoxycarbonylethyl)-2,6-dialkylanilines |
| US4260782A (en) * | 1980-06-09 | 1981-04-07 | Ciba-Geigy Corporation | Process for the preparation of N-(1'-alkoxycarbonylethyl)-2,6-dialkylanilines |
| DE3037160C2 (de) * | 1980-10-01 | 1982-09-23 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von optisch aktiven 2-Anilinopropionsäureestern |
| US4460603A (en) * | 1980-11-17 | 1984-07-17 | Chevron Research Company | 1-(2'-Haloalkyl)-amidomethyl-substituted acetanilide fungicides |
| DE3206235A1 (de) * | 1982-02-20 | 1983-09-01 | Bayer Ag, 5090 Leverkusen | Substituierte oximinoacetanilide, verfahren zu ihrer herstellung sowie ihre verwendung als schaedlingsbekaempfungsmittel |
| US4492683A (en) * | 1982-08-06 | 1985-01-08 | Buffalo Color Corporation | Method for inhibiting the growth of fungi with phenyl glycine compounds |
| DD256072A1 (de) * | 1985-03-04 | 1988-04-27 | Adl Der Ddr Inst Fuer Pflanzen | Fungizide und pflanzenwachstumsregulierende mittel |
| EP0230209A3 (fr) * | 1985-12-16 | 1987-08-12 | Ciba-Geigy Ag | Microbicides |
| RU2680309C1 (ru) * | 2018-02-13 | 2019-02-19 | Андрей Васильевич Кудряшов | Средство для защиты растений "Агройод" |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR6340M (fr) * | 1967-04-11 | 1968-09-30 | ||
| US3712805A (en) * | 1967-12-28 | 1973-01-23 | Shell Oil Co | Weed control employing n,n-disubstituted amino acid herbicides |
| US3892786A (en) * | 1969-03-12 | 1975-07-01 | Stauffer Chemical Co | Bromoacetanilides and their utility as biocides |
| US3780095A (en) * | 1970-04-08 | 1973-12-18 | Byk Gulden Lomberg Chem Fab | Acylated anilino-carboxylic acids and their salts |
| 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 |
| JPS5119020B2 (fr) * | 1973-02-16 | 1976-06-14 |
-
1975
- 1975-03-25 FR FR7509240A patent/FR2265726B1/fr not_active Expired
- 1975-03-26 SE SE7503516A patent/SE411450B/xx unknown
- 1975-03-26 DK DK136075AA patent/DK141118B/da not_active IP Right Cessation
- 1975-03-26 FI FI750919A patent/FI61476C/fi not_active IP Right Cessation
- 1975-03-26 NO NO751085A patent/NO144962C/no unknown
- 1975-03-27 HU HU75CI1559A patent/HU173316B/hu not_active IP Right Cessation
- 1975-03-27 DE DE2513730A patent/DE2513730C2/de not_active Expired
- 1975-03-27 GB GB12989/75A patent/GB1495348A/en not_active Expired
- 1975-03-27 NL NL7503758A patent/NL7503758A/xx not_active Application Discontinuation
- 1975-03-27 IE IE696/75A patent/IE41102B1/xx unknown
- 1975-03-27 AT AT238575A patent/AT343406B/de not_active IP Right Cessation
- 1975-03-27 US US05/562,741 patent/US4032657A/en not_active Expired - Lifetime
- 1975-03-31 ES ES436153A patent/ES436153A1/es not_active Expired
- 1975-03-31 RO RO7581847A patent/RO70589A/fr unknown
- 1975-03-31 PH PH16994A patent/PH11591A/en unknown
- 1975-03-31 IL IL46968A patent/IL46968A/xx unknown
- 1975-03-31 BG BG029500A patent/BG26508A3/xx unknown
- 1975-03-31 DD DD185110A patent/DD118788A5/xx unknown
- 1975-03-31 OA OA55459A patent/OA04917A/fr unknown
- 1975-03-31 AR AR258181A patent/AR209297A1/es active
- 1975-04-01 JP JP50039728A patent/JPS5910321B2/ja not_active Expired
- 1975-04-01 SU SU752120302A patent/SU692535A3/ru active
- 1975-04-01 LU LU72173A patent/LU72173A1/xx unknown
- 1975-04-01 TR TR18662A patent/TR18662A/xx unknown
- 1975-04-01 EG EG183/75A patent/EG12082A/xx active
- 1975-04-01 CS CS7500002211A patent/CS183787B2/cs unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK150848B (da) * | 1976-09-17 | 1987-07-06 | Ciba Geigy | N-substituerede sulfonylglycolsyreanilider med fungicid virkning mod fytopatogene svampe samt anvendelse deraf til bekaempelse af fytopatogene svampe |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DK141168B (da) | Fungicide anilidforbindelser til anvendelse ved plantebeskyttelse. | |
| DK141118B (da) | Fungicide halogenacetanilider til anvendelse ved plantebeskyttelse. | |
| DK142360B (da) | Fungicide N-acyl-anilinoeddikesyrederivater til anvendelse ved plantebeskyttelse. | |
| JPS6254096B2 (fr) | ||
| IE43632B1 (en) | Amino acid anilides having microbicidal activity | |
| US4143155A (en) | Sulfonylglycolic anilide fungicides | |
| US4025648A (en) | Haloacylanilides and use as fungicides | |
| US4046911A (en) | N-(substituted phenyl)-n-furanoyl-alanine methyl esters and their use in fungicidal composition and methods | |
| DK141440B (da) | Fungicide N-acyl-anilinoeddikesyreestere til anvendelse ved plantebeskyttelse. | |
| US4075349A (en) | Microbicidal compositions | |
| US4233308A (en) | Microbicidal compositions | |
| JPH0234939B2 (fr) | ||
| JPS648615B2 (fr) | ||
| CS219337B2 (en) | Fungicide means and method of making the active ingredients | |
| JPS629105B2 (fr) | ||
| US4207338A (en) | Microbicidal composition | |
| US4101672A (en) | Microbicidal alanine thioesters | |
| FI61475C (fi) | Saosom vaextfungicider anvaendbara haloacylanilider | |
| HU185884B (en) | Fungicide compositions containing n-allenyl-acetanilides and process for preparing such compounds | |
| US4224337A (en) | Pesticidal compositions | |
| CH618842A5 (en) | Pesticides | |
| JPS6250469B2 (fr) | ||
| CH608690A5 (en) | Microbicidal composition | |
| CH603042A5 (en) | Microbicidal N-phenyl-N-haloacetyl-alanine methyl ester cpds. |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PBP | Patent lapsed |