CH627342A5 - Plant growth regulator containing, as active substance, a hydroxamic acid derivative - Google Patents

Plant growth regulator containing, as active substance, a hydroxamic acid derivative Download PDF

Info

Publication number: CH627342A5
Authority: CH; Switzerland
Prior art keywords: formula; growth; ethyl; acid; methyl
Prior art date: 1976-03-09

Application number

CH289876A

Other languages

German (de)

English (en)

Inventor

Hans Dr Moser

Rolf Dr Schurter

Original Assignee

Ciba Geigy Ag

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.)

1976-03-09

Filing date

1976-03-09

Publication date

1982-01-15

1976-03-09 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1976-03-09 Priority to CH289876A priority Critical patent/CH627342A5/de

1977-02-22 Priority to NL7701888A priority patent/NL7701888A/xx

1977-02-28 Priority to US05/772,420 priority patent/US4126440A/en

1977-03-07 Priority to CA273,310A priority patent/CA1080746A/fr

1977-03-07 Priority to DE19772709854 priority patent/DE2709854A1/de

1977-03-07 Priority to FR7706582A priority patent/FR2343722A1/fr

1977-03-07 Priority to IL51610A priority patent/IL51610A/xx

1977-03-08 Priority to ES77456608A priority patent/ES456608A1/es

1977-03-08 Priority to GB9669/77A priority patent/GB1570228A/en

1977-03-08 Priority to ZA00771404A priority patent/ZA771404B/xx

1977-03-08 Priority to IT21042/77A priority patent/IT1075492B/it

1977-03-08 Priority to BE175567A priority patent/BE852197A/fr

1977-03-08 Priority to AU23002/77A priority patent/AU513600B2/en

1977-03-09 Priority to BR7701405A priority patent/BR7701405A/pt

1977-03-09 Priority to JP2588377A priority patent/JPS52108936A/ja

1982-01-15 Publication of CH627342A5 publication Critical patent/CH627342A5/de

Links

239000002253 acid Substances 0.000 title claims abstract description 17
NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 title claims abstract description 12
239000013543 active substance Substances 0.000 title abstract description 6
239000005648 plant growth regulator Substances 0.000 title abstract 2
230000012010 growth Effects 0.000 claims abstract description 23
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 10
238000002360 preparation method Methods 0.000 claims abstract description 10
241000209504 Poaceae Species 0.000 claims abstract description 9
230000002401 inhibitory effect Effects 0.000 claims abstract description 8
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
239000001257 hydrogen Substances 0.000 claims abstract description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
239000004480 active ingredient Substances 0.000 claims description 34
150000001875 compounds Chemical class 0.000 claims description 27
241000196324 Embryophyta Species 0.000 claims description 24
239000000203 mixture Substances 0.000 claims description 16
-1 N-substituted phenylamines Chemical class 0.000 claims description 14
235000013339 cereals Nutrition 0.000 claims description 12
239000003795 chemical substances by application Substances 0.000 claims description 12
UGIUIFDIFSBIBH-UHFFFAOYSA-N 2-(n-(2-chloroacetyl)-2,6-dimethylanilino)acetic acid Chemical compound CC1=CC=CC(C)=C1N(CC(O)=O)C(=O)CCl UGIUIFDIFSBIBH-UHFFFAOYSA-N 0.000 claims description 11
238000000034 method Methods 0.000 claims description 10
230000008635 plant growth Effects 0.000 claims description 9
239000004009 herbicide Substances 0.000 claims description 7
235000010469 Glycine max Nutrition 0.000 claims description 6
244000068988 Glycine max Species 0.000 claims description 6
244000025254 Cannabis sativa Species 0.000 claims description 5
240000005979 Hordeum vulgare Species 0.000 claims description 5
235000007340 Hordeum vulgare Nutrition 0.000 claims description 5
241000209140 Triticum Species 0.000 claims description 4
235000021307 Triticum Nutrition 0.000 claims description 4
150000008064 anhydrides Chemical class 0.000 claims description 4
230000002363 herbicidal effect Effects 0.000 claims description 4
230000009467 reduction Effects 0.000 claims description 4
IHNGFMNOFGWIEZ-UHFFFAOYSA-N 2-(n-(2-chloroacetyl)-2,6-diethylanilino)butanoic acid Chemical compound CCC(C(O)=O)N(C(=O)CCl)C1=C(CC)C=CC=C1CC IHNGFMNOFGWIEZ-UHFFFAOYSA-N 0.000 claims description 3
239000000654 additive Substances 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
239000000969 carrier Substances 0.000 claims description 3
230000003111 delayed effect Effects 0.000 claims description 3
230000000694 effects Effects 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 3
230000005094 fruit set Effects 0.000 claims description 3
238000004904 shortening Methods 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
230000009105 vegetative growth Effects 0.000 claims description 3
MFUUKPXESMFXBH-UHFFFAOYSA-N 2-(n-(2-chloroacetyl)anilino)acetic acid Chemical compound OC(=O)CN(C(=O)CCl)C1=CC=CC=C1 MFUUKPXESMFXBH-UHFFFAOYSA-N 0.000 claims description 2
PERLAUCSKSAHSO-UHFFFAOYSA-N 2-anilino-n-(2-chloroacetyl)acetamide Chemical class ClCC(=O)NC(=O)CNC1=CC=CC=C1 PERLAUCSKSAHSO-UHFFFAOYSA-N 0.000 claims description 2
208000012766 Growth delay Diseases 0.000 claims description 2
241000735234 Ligustrum Species 0.000 claims description 2
244000172730 Rubus fruticosus Species 0.000 claims description 2
235000021029 blackberry Nutrition 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims description 2
238000005520 cutting process Methods 0.000 claims description 2
230000006378 damage Effects 0.000 claims description 2
239000003966 growth inhibitor Substances 0.000 claims description 2
238000003306 harvesting Methods 0.000 claims description 2
238000004162 soil erosion Methods 0.000 claims description 2
244000045561 useful plants Species 0.000 claims description 2
238000009333 weeding Methods 0.000 claims description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 11
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
150000001408 amides Chemical class 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000000839 emulsion Substances 0.000 description 6
239000008187 granular material Substances 0.000 description 6
239000005995 Aluminium silicate Substances 0.000 description 5
235000012211 aluminium silicate Nutrition 0.000 description 5
239000012141 concentrate Substances 0.000 description 5
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 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
240000007594 Oryza sativa Species 0.000 description 4
235000007164 Oryza sativa Nutrition 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
229920000151 polyglycol Polymers 0.000 description 4
239000010695 polyglycol Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
ISERORSDFSDMDV-UHFFFAOYSA-N 2-(n-(2-chloroacetyl)-2,6-diethylanilino)acetic acid Chemical compound CCC1=CC=CC(CC)=C1N(CC(O)=O)C(=O)CCl ISERORSDFSDMDV-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
239000002202 Polyethylene glycol Substances 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
229940106681 chloroacetic acid Drugs 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
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 3
229920001223 polyethylene glycol Polymers 0.000 description 3
235000009566 rice Nutrition 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000009331 sowing Methods 0.000 description 3
239000007921 spray Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 3
239000004563 wettable powder Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
239000007832 Na2SO4 Substances 0.000 description 2
235000002637 Nicotiana tabacum Nutrition 0.000 description 2
244000061176 Nicotiana tabacum 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
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
239000003513 alkali Substances 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
239000002585 base Substances 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
238000011156 evaluation Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Natural products O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
230000009036 growth inhibition Effects 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
230000017066 negative regulation of growth Effects 0.000 description 2
239000004033 plastic Substances 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
239000000843 powder Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000000376 reactant Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000004576 sand Substances 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000002689 soil Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
235000015112 vegetable and seed oil Nutrition 0.000 description 2
239000008158 vegetable oil 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
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
WOKGGLSYQGJYTP-UHFFFAOYSA-N 2-(n-(2-chloroacetyl)-2-ethyl-6-methylanilino)acetic acid Chemical compound CCC1=CC=CC(C)=C1N(CC(O)=O)C(=O)CCl WOKGGLSYQGJYTP-UHFFFAOYSA-N 0.000 description 1
GXBRYTMUEZNYJT-UHFFFAOYSA-N 2-anilinoacetamide Chemical compound NC(=O)CNC1=CC=CC=C1 GXBRYTMUEZNYJT-UHFFFAOYSA-N 0.000 description 1
LKRZCUQFUCYWLZ-UHFFFAOYSA-N 2-chloroacetyl bromide Chemical compound ClCC(Br)=O LKRZCUQFUCYWLZ-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
240000004585 Dactylis glomerata Species 0.000 description 1
WFKSADNZWSKCRZ-UHFFFAOYSA-N Diethatyl-ethyl Chemical compound CCOC(=O)CN(C(=O)CCl)C1=C(CC)C=CC=C1CC WFKSADNZWSKCRZ-UHFFFAOYSA-N 0.000 description 1
241000410074 Festuca ovina Species 0.000 description 1
240000004296 Lolium perenne Species 0.000 description 1
SXZPBDICBKEBCG-UHFFFAOYSA-N N-ethoxy-N-methylhydroxylamine Chemical compound C(C)ON(C)O SXZPBDICBKEBCG-UHFFFAOYSA-N 0.000 description 1
NPKSPKHJBVJUKB-UHFFFAOYSA-N N-phenylglycine Chemical class OC(=O)CNC1=CC=CC=C1 NPKSPKHJBVJUKB-UHFFFAOYSA-N 0.000 description 1
IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
241000209049 Poa pratensis Species 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
241000219793 Trifolium Species 0.000 description 1
244000098338 Triticum aestivum Species 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
DNEHKUCSURWDGO-UHFFFAOYSA-N aluminum sodium Chemical compound [Na].[Al] DNEHKUCSURWDGO-UHFFFAOYSA-N 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
239000002518 antifoaming agent Substances 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
230000003115 biocidal effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
235000019993 champagne Nutrition 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
150000001983 dialkylethers Chemical class 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000012467 final product Substances 0.000 description 1
NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
230000001408 fungistatic effect Effects 0.000 description 1
238000000227 grinding Methods 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
KRKPYFLIYNGWTE-UHFFFAOYSA-N n,o-dimethylhydroxylamine Chemical compound CNOC KRKPYFLIYNGWTE-UHFFFAOYSA-N 0.000 description 1
AANPZKMNFXPEOQ-UHFFFAOYSA-N n-methylhydroxylamine;oxalic acid Chemical compound CNO.OC(=O)C(O)=O AANPZKMNFXPEOQ-UHFFFAOYSA-N 0.000 description 1
230000001069 nematicidal effect Effects 0.000 description 1
239000005645 nematicide Substances 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
125000001117 oleyl 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])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000006072 paste Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
230000026267 regulation of growth Effects 0.000 description 1
230000000979 retarding effect Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
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 1
238000001228 spectrum Methods 0.000 description 1
238000005728 strengthening Methods 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
KLBOFRLEHJAXIU-UHFFFAOYSA-N tributylazanium;chloride Chemical compound Cl.CCCCN(CCCC)CCCC KLBOFRLEHJAXIU-UHFFFAOYSA-N 0.000 description 1
230000003442 weekly effect Effects 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon

Landscapes

Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Dentistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Plant Pathology (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH289876A 1976-03-09 1976-03-09 Plant growth regulator containing, as active substance, a hydroxamic acid derivative CH627342A5 (en)

Priority Applications (15)

Application Number	Priority Date	Filing Date	Title
CH289876A CH627342A5 (en)	1976-03-09	1976-03-09	Plant growth regulator containing, as active substance, a hydroxamic acid derivative
NL7701888A NL7701888A (nl)	1976-03-09	1977-02-22	Hydroxamzuurderivaten ter beinvloeding van de plantengroei.
US05/772,420 US4126440A (en)	1976-03-09	1977-02-28	Hydroxamic acid derivatives for regulating plant growth
CA273,310A CA1080746A (fr)	1976-03-09	1977-03-07	Derives d'acide hydroxamique comme regulateurs de la croissange vegetale
DE19772709854 DE2709854A1 (de)	1976-03-09	1977-03-07	Hydroxamsaeure-derivate zur beeinflussung des pflanzenwachstums
FR7706582A FR2343722A1 (fr)	1976-03-09	1977-03-07	Derives d'acide hydroxamique pour influencer la croissance des plantes
IL51610A IL51610A (en)	1976-03-09	1977-03-07	2,6-dialkyl n-hydroxylamino carbonyl chloroacetanilide derivatives,their production and plant growth regulating compositions containing them
ES77456608A ES456608A1 (es)	1976-03-09	1977-03-08	Procedimiento para la preparacion de derivados de acido hi- droxamico.
GB9669/77A GB1570228A (en)	1976-03-09	1977-03-08	Hydroxamic acid derivatives and plant growth regulating compositions containing them
ZA00771404A ZA771404B (en)	1976-03-09	1977-03-08	Hydroxamic acid derivatives for regulating plant growth
IT21042/77A IT1075492B (it)	1976-03-09	1977-03-08	Derivati dell'acido idrossammico,procedimento per la loro preparazione e loro impiego per influire sulla crescita delle piante
BE175567A BE852197A (fr)	1976-03-09	1977-03-08	Derives d'acide hydroxamique pour influencer la croissance des plantes
AU23002/77A AU513600B2 (en)	1976-03-09	1977-03-08	Hydroxamic acid derivatives
BR7701405A BR7701405A (pt)	1976-03-09	1977-03-09	Derivados de acido hidroxamico,processo para sua preparacao e composicao e processo para retardar e inibir o crescimento de plantas
JP2588377A JPS52108936A (en)	1976-03-09	1977-03-09	Hydroxamic acid derivative* prparati of therof and plant growth rgulation composition containing same

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH289876A CH627342A5 (en)	1976-03-09	1976-03-09	Plant growth regulator containing, as active substance, a hydroxamic acid derivative

Publications (1)

Publication Number	Publication Date
CH627342A5 true CH627342A5 (en)	1982-01-15

Family

ID=4244092

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH289876A CH627342A5 (en)	1976-03-09	1976-03-09	Plant growth regulator containing, as active substance, a hydroxamic acid derivative

Country Status (3)

Country	Link
BE (1)	BE852197A (fr)
CH (1)	CH627342A5 (fr)
ZA (1)	ZA771404B (fr)

1976
- 1976-03-09 CH CH289876A patent/CH627342A5/de not_active IP Right Cessation
1977
- 1977-03-08 ZA ZA00771404A patent/ZA771404B/xx unknown
- 1977-03-08 BE BE175567A patent/BE852197A/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
BE852197A (fr)	1977-09-08
ZA771404B (en)	1978-02-22

Legal Events

Date	Code	Title	Description
1987-11-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
EP0000176B1 (fr)	1981-09-16	Dérivés d'acides pyridyloxy-phénoxy-alcanoîques, leurs procédés de préparation et leur utilisation comme régulateurs de croissance pour plantes
DE2657728C2 (fr)	1987-09-24
DE2650604A1 (de)	1977-05-12	Mittel und verfahren zur beeinflussung des pflanzenwachstums und neue 1-phenyl-2-oxo-pyrrolidin-4- carbonsaeurederivate
DE2639405A1 (de)	1977-03-17	Neuer oximaether, verfahren zu dessen herstellung und seine verwendung als gegenmittel fuer kulturpflanzen schaedigende herbizide
DD223147A5 (de)	1985-06-05	Verfahren zur herstellung von cyclohexandion-carbonsaeurederivaten
CH621921A5 (fr)	1981-03-13
CH644371A5 (de)	1984-07-31	In 2- und 4-stellung disubstituierte 5-thiazolcarbonsaeuren und deren funktionelle derivate.
EP0017946B1 (fr)	1982-04-14	Sels d'alpha-aminoacétanilides, procédé pour leur préparation et leur utilisation comme régulateurs de la croissance des plantes
DE2744137C2 (de)	1984-05-10	N,N-Disubstituierte Benzolsulfonamid-Derivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende herbizide Zusammensetzung
EP0036390B1 (fr)	1983-10-26	Diphényléther-urées à propriétés herbicides
DE1618644C3 (de)	1979-10-04	zu ihrer Herstellung und sie enthaltende Herbicide
DD149935A5 (de)	1981-08-05	Verfahren zur herstellung von racemen oder optisch aktivem 2-(propargyloxyimino)-1,7,7-trimethylbicyclo(2,2,1)heptan
EP0010692B1 (fr)	1982-06-23	N-m-Anilidocarbamates, herbicides les contenant et procédé pour leur préparation ainsi que procédé pour contrôler la croissance de plantes indésirables
DE2709854A1 (de)	1977-09-15	Hydroxamsaeure-derivate zur beeinflussung des pflanzenwachstums
DD262992A5 (de)	1988-12-21	Nematizide und insektizide zusammensetzung
DE2114094A1 (de)	1971-10-14	Unkrautbekaempfungsmittel
DE3300056C2 (de)	1985-06-27	3-Nitrobenzolsulfonanilid-Derivate und diese enthaltende fungizide Mittel
EP0050097A1 (fr)	1982-04-21	Dérivés de l'acide alpha-(pyridyl-2-oxy-phénoxy)-propionique, procédé pour leur préparation et leur utilisation comme herbicide et/ou régulateurs de croissance de plantes
DE2428070A1 (de)	1975-01-09	Butyramide und butyrate und ihre herstellung und anwendung
EP0023539B1 (fr)	1983-01-12	Esters alkyliques de l'acide 3-(N-1,3,4-thiadiazolyl-2)-amino-alkyle acrylique, procédé pour leur préparation et leur utilisation comme bactéricides pour plantes
DE2154634A1 (fr)	1972-05-10
DE2826531C2 (fr)	1988-04-14
EP0040310A2 (fr)	1981-11-25	Thioglycol anilides à substitution hétérocyclique et à activité fongicide, leur préparation, et pesticides les contenant
EP0016731B1 (fr)	1983-02-16	Méta-cyanoalcoxy-phénylurées à activité herbicide, leur préparation et compositions les contenant
CH593606A5 (en)	1977-12-15	Substd. chloro acetyl phenyl amino acetamides - having plant growth inhibiting activity without phytotoxic effect