CH634067A5 - Thiophenecarboxamidoxime derivatives, their preparation and phytohormonal and herbicidal compositions containing them - Google Patents

Thiophenecarboxamidoxime derivatives, their preparation and phytohormonal and herbicidal compositions containing them Download PDF

Info

Publication number: CH634067A5
Authority: CH; Switzerland
Prior art keywords: carbon atoms; radical; formula; alkyl; compound
Prior art date: 1977-07-28

Application number

CH816578A

Other languages

English (en)

French (fr)

Inventor

Daniel Farge

Jean Leboul

Yves Le Goff

Gilbert Poiget

Original Assignee

Philagro Sa

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.)

1977-07-28

Filing date

1978-07-28

Publication date

1983-01-14

1978-07-28 Application filed by Philagro Sa filed Critical Philagro Sa

1983-01-14 Publication of CH634067A5 publication Critical patent/CH634067A5/fr

Links

239000000203 mixture Substances 0.000 title claims description 24
238000002360 preparation method Methods 0.000 title claims description 11
230000002363 herbicidal effect Effects 0.000 title claims description 4
NKMNPRXPUZINOM-UHFFFAOYSA-N n'-hydroxythiophene-2-carboximidamide Chemical class ON=C(N)C1=CC=CS1 NKMNPRXPUZINOM-UHFFFAOYSA-N 0.000 title claims description 3
150000001875 compounds Chemical class 0.000 claims description 37
125000004432 carbon atom Chemical group C* 0.000 claims description 28
239000011149 active material Substances 0.000 claims description 12
-1 trifluoromethoxy, trifluoromethylthio, carboxy Chemical group 0.000 claims description 9
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical class [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 7
238000011282 treatment Methods 0.000 claims description 7
238000000034 method Methods 0.000 claims description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
239000004094 surface-active agent Substances 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical class C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
229910052799 carbon Inorganic materials 0.000 claims 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
125000002252 acyl group Chemical group 0.000 claims 1
125000004442 acylamino group Chemical group 0.000 claims 1
125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 1
125000003282 alkyl amino group Chemical group 0.000 claims 1
125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
125000004414 alkyl thio group Chemical group 0.000 claims 1
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 1
125000001589 carboacyl group Chemical group 0.000 claims 1
125000005842 heteroatom Chemical group 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
239000002184 metal Chemical group 0.000 claims 1
125000004433 nitrogen atom Chemical group N* 0.000 claims 1
229910052760 oxygen Inorganic materials 0.000 claims 1
239000001301 oxygen Substances 0.000 claims 1
125000001424 substituent group Chemical group 0.000 claims 1
229910052717 sulfur Inorganic materials 0.000 claims 1
239000011593 sulfur Substances 0.000 claims 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
239000000243 solution Substances 0.000 description 12
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
150000003254 radicals Chemical class 0.000 description 9
239000000047 product Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000004480 active ingredient Substances 0.000 description 6
239000013078 crystal Substances 0.000 description 6
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
235000007688 Lycopersicon esculentum Nutrition 0.000 description 5
240000003768 Solanum lycopersicum Species 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
241000196324 Embryophyta Species 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
241000220259 Raphanus Species 0.000 description 4
235000006140 Raphanus sativus var sativus Nutrition 0.000 description 4
239000000853 adhesive Substances 0.000 description 4
230000001070 adhesive effect Effects 0.000 description 4
239000004495 emulsifiable concentrate Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
239000000843 powder Substances 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
239000003381 stabilizer Substances 0.000 description 4
239000000080 wetting agent Substances 0.000 description 4
241000335053 Beta vulgaris Species 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
241000219739 Lens Species 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
241000209140 Triticum Species 0.000 description 3
235000021307 Triticum Nutrition 0.000 description 3
239000000654 additive Substances 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
239000002270 dispersing agent Substances 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
235000013399 edible fruits Nutrition 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000000155 melt Substances 0.000 description 3
230000000149 penetrating effect Effects 0.000 description 3
241000894007 species Species 0.000 description 3
238000005507 spraying Methods 0.000 description 3
239000004563 wettable powder Substances 0.000 description 3
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
VNDWQCSOSCCWIP-UHFFFAOYSA-N 2-tert-butyl-9-fluoro-1,6-dihydrobenzo[h]imidazo[4,5-f]isoquinolin-7-one Chemical compound C1=2C=CNC(=O)C=2C2=CC(F)=CC=C2C2=C1NC(C(C)(C)C)=N2 VNDWQCSOSCCWIP-UHFFFAOYSA-N 0.000 description 2
LLKFNPUXQZHIAE-UHFFFAOYSA-N 5-(3-aminopropyl)-8-bromo-3-methyl-2h-pyrazolo[4,3-c]quinolin-4-one Chemical compound O=C1N(CCCN)C2=CC=C(Br)C=C2C2=C1C(C)=NN2 LLKFNPUXQZHIAE-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
240000001592 Amaranthus caudatus Species 0.000 description 2
235000009328 Amaranthus caudatus Nutrition 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
235000016068 Berberis vulgaris Nutrition 0.000 description 2
244000043158 Lens esculenta Species 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
240000008042 Zea mays Species 0.000 description 2
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
235000002017 Zea mays subsp mays Nutrition 0.000 description 2
239000002253 acid Substances 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000000084 colloidal system Substances 0.000 description 2
239000007859 condensation product Substances 0.000 description 2
235000005822 corn Nutrition 0.000 description 2
230000007797 corrosion Effects 0.000 description 2
238000005260 corrosion Methods 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
230000006378 damage Effects 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
238000010410 dusting Methods 0.000 description 2
239000000975 dye Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000012530 fluid Substances 0.000 description 2
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000011707 mineral Substances 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
230000001681 protective effect Effects 0.000 description 2
239000002994 raw material Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000002689 soil Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000013008 thixotropic agent Substances 0.000 description 2
YQYGGOPUTPQHAY-KIQLFZLRSA-N (4S)-4-[[(2S)-2-[[(2S)-2-[2-[6-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S,3S)-1-[[(2S)-5-amino-1-[[(4S,7R)-7-[[(2S)-1-[(2S)-6-amino-2-[[(2R)-2-[[(2S)-5-amino-2-[[(2S,3R)-2-[[(2S)-6-amino-2-[[(2S)-4-carboxy-2-hydrazinylbutanoyl]amino]hexanoyl]amino]-3-methylpentanoyl]amino]-5-oxopentanoyl]amino]propanoyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-2-methyl-5,6-dioxooctan-4-yl]amino]-1,5-dioxopentan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-5-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-4-amino-2-[[(2S)-2-amino-3-hydroxypropanoyl]amino]-4-oxobutanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxypropanoyl]amino]-4-carboxybutanoyl]amino]-3-hydroxypropanoyl]amino]-3-phenylpropanoyl]amino]-6-oxohexyl]hydrazinyl]-3-phenylpropanoyl]amino]-3-hydroxypropanoyl]amino]-5-[[(2S)-1-[[(2S,3S)-1-[[(2S)-4-amino-1-[[(2S)-1-hydroxy-3-oxopropan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-5-oxopentanoic acid Chemical compound CC[C@@H](C)[C@H](NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(O)=O)NN)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@H](C)C(=O)N[C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)N[C@H](C)C(=O)C(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](Cc1ccccc1)NC(=O)C(CCCCNN[C@@H](Cc1ccccc1)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CO)C=O)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](N)CO)[C@H](C)O)C(C)C)[C@H](C)O YQYGGOPUTPQHAY-KIQLFZLRSA-N 0.000 description 1
241001621841 Alopecurus myosuroides Species 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
235000021537 Beetroot Nutrition 0.000 description 1
235000021533 Beta vulgaris Nutrition 0.000 description 1
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
244000025254 Cannabis sativa Species 0.000 description 1
RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
239000001692 EU approved anti-caking agent Substances 0.000 description 1
235000014647 Lens culinaris subsp culinaris Nutrition 0.000 description 1
235000010666 Lens esculenta Nutrition 0.000 description 1
IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
235000019057 Raphanus caudatus Nutrition 0.000 description 1
244000088415 Raphanus sativus Species 0.000 description 1
235000011380 Raphanus sativus Nutrition 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229920002125 Sokalan® Polymers 0.000 description 1
235000021536 Sugar beet Nutrition 0.000 description 1
244000098338 Triticum aestivum Species 0.000 description 1
WERKSKAQRVDLDW-ANOHMWSOSA-N [(2s,3r,4r,5r)-2,3,4,5,6-pentahydroxyhexyl] (z)-octadec-9-enoate Chemical class CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO WERKSKAQRVDLDW-ANOHMWSOSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 1
230000002528 anti-freeze Effects 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
238000007865 diluting Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
239000000428 dust Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
241001233957 eudicotyledons Species 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
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 1
150000002576 ketones Chemical class 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
239000008268 mayonnaise Substances 0.000 description 1
235000010746 mayonnaise Nutrition 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
230000000361 pesticidal effect Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical class OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229940072033 potash Drugs 0.000 description 1
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
238000004382 potting Methods 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
ARENMZZMCSLORU-UHFFFAOYSA-N propan-2-yl naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)OC(C)C)=CC=CC2=C1 ARENMZZMCSLORU-UHFFFAOYSA-N 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000004576 sand Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000013049 sediment Substances 0.000 description 1
238000004062 sedimentation Methods 0.000 description 1
239000003352 sequestering agent Substances 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
238000009331 sowing Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000012085 test solution Substances 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
239000001993 wax Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom

Landscapes

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

CH816578A 1977-07-28 1978-07-28 Thiophenecarboxamidoxime derivatives, their preparation and phytohormonal and herbicidal compositions containing them CH634067A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR7724114A FR2398744A2 (fr)	1977-07-28	1977-07-28	Nouveaux derives d'amidoximes, leur preparation et les compositions qui les contiennent

Publications (1)

Publication Number	Publication Date
CH634067A5 true CH634067A5 (en)	1983-01-14

Family

ID=9194251

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH816578A CH634067A5 (en)	1977-07-28	1978-07-28	Thiophenecarboxamidoxime derivatives, their preparation and phytohormonal and herbicidal compositions containing them

Country Status (18)

Country	Link
JP (1)	JPS5427558A (pl)
AT (1)	AT365586B (pl)
BE (1)	BE869383R (pl)
BR (1)	BR7804865A (pl)
CH (1)	CH634067A5 (pl)
DD (1)	DD137181A5 (pl)
DE (1)	DE2831983A1 (pl)
DK (1)	DK334578A (pl)
ES (1)	ES472090A2 (pl)
FR (1)	FR2398744A2 (pl)
GB (1)	GB1576646A (pl)
HU (1)	HU180918B (pl)
IE (1)	IE47162B1 (pl)
IT (1)	IT1112650B (pl)
LU (1)	LU80050A1 (pl)
NL (1)	NL7807969A (pl)
PL (1)	PL112882B1 (pl)
SE (1)	SE7808241L (pl)

1977
- 1977-07-28 FR FR7724114A patent/FR2398744A2/fr active Granted
1978
- 1978-05-23 GB GB21684/78A patent/GB1576646A/en not_active Expired
- 1978-07-20 DE DE19782831983 patent/DE2831983A1/de not_active Withdrawn
- 1978-07-26 IE IE1511/78A patent/IE47162B1/en unknown
- 1978-07-27 DK DK334578A patent/DK334578A/da not_active Application Discontinuation
- 1978-07-27 DD DD78206977A patent/DD137181A5/xx unknown
- 1978-07-27 JP JP9202778A patent/JPS5427558A/ja active Pending
- 1978-07-27 PL PL1978208678A patent/PL112882B1/pl unknown
- 1978-07-27 ES ES472090A patent/ES472090A2/es not_active Expired
- 1978-07-27 LU LU80050A patent/LU80050A1/fr unknown
- 1978-07-27 BR BR7804865A patent/BR7804865A/pt unknown
- 1978-07-27 NL NL7807969A patent/NL7807969A/xx not_active Application Discontinuation
- 1978-07-28 SE SE7808241A patent/SE7808241L/xx unknown
- 1978-07-28 IT IT26286/78A patent/IT1112650B/it active
- 1978-07-28 CH CH816578A patent/CH634067A5/fr not_active IP Right Cessation
- 1978-07-28 HU HU78PI633A patent/HU180918B/hu unknown
- 1978-07-28 AT AT0552178A patent/AT365586B/de not_active IP Right Cessation
- 1978-07-28 BE BE189598A patent/BE869383R/xx active

Also Published As

Publication number	Publication date
FR2398744B2 (pl)	1980-01-18
JPS5427558A (en)	1979-03-01
DK334578A (da)	1979-01-29
DE2831983A1 (de)	1979-02-15
LU80050A1 (fr)	1980-02-14
GB1576646A (en)	1980-10-15
PL112882B1 (en)	1980-11-29
HU180918B (en)	1983-05-30
AT365586B (de)	1982-01-25
PL208678A1 (pl)	1979-09-10
IE781511L (en)	1979-01-28
SE7808241L (sv)	1979-01-29
NL7807969A (nl)	1979-01-30
IT7826286A0 (it)	1978-07-28
IT1112650B (it)	1986-01-20
DD137181A5 (de)	1979-08-22
ATA552178A (de)	1981-06-15
FR2398744A2 (fr)	1979-02-23
BR7804865A (pt)	1979-04-24
IE47162B1 (en)	1984-01-11
BE869383R (fr)	1979-01-29
ES472090A2 (es)	1979-10-16

Legal Events

Date	Code	Title	Description
1985-03-29	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
EP0087375B1 (fr)	1985-09-18	Nouveaux dérivés du cyano-2 benzimidazole, leur préparation et leur utilisation comme fongicides et acaricides
EP0135454B1 (fr)	1989-05-31	Herbicides de type sulfonimide à groupe aminométhylphosphonique
FR2559150A1 (fr)	1985-08-09	Nouveaux derives du cyano-2 benzimidazole, leur preparation et leur utilisation comme fongicides
EP0044262B1 (fr)	1983-11-23	Nouveaux dérivés de l'aniline, leur préparation et leur application pour le désherbage sélectif de cultures
EP0069033A1 (fr)	1983-01-05	Herbicides à fonction amide et ester dérivés de la pyridine ainsi que leur procédé de préparation et leur application
EP0239508A2 (fr)	1987-09-30	Nouveaux dérivés du cyano-2 benzimidazole, leur préparation et leur utilisation comme fongicide, leur association avec d'autres fongicides
EP0189358B1 (fr)	1988-09-28	Herbicides de type N-(phosphonométhylglycyl) sulfonylamines
EP0122206A2 (fr)	1984-10-17	Nouveaux dérivés de cyano-2 imidazopyridine, leur préparation et leur utilisation comme fongicides
EP0034556B1 (fr)	1984-02-01	Compositions régulatrices de la croissance des plantes contenant comme matière active des dérivés de l'acide méthylène-2 succinamique et nouveaux dérivés de cet acide utilisables dans ces compositions
CH634067A5 (en)	1983-01-14	Thiophenecarboxamidoxime derivatives, their preparation and phytohormonal and herbicidal compositions containing them
EP0012703B1 (fr)	1981-11-04	Dérivés de phosphates de N-phényle N-(alcoxycarbonylalcoyle)acétamides, procédé pour leur préparation et les compositions fongicides les contenant
EP0060955B1 (fr)	1985-05-08	Nouveaux uraciles substitués comportant un groupement 2-tétra-hydropyranyle, leur procédé de préparation et les compositions pesticides les renfermant
EP0014167B1 (fr)	1982-06-30	Produits dérivés de l'aniline ayant une activité antifongique ainsi que leur procédé de préparation
FR2560007A1 (fr)	1985-08-30	Compositions fongicides comprenant des derives de phenoxy benzaldehyde
EP0077281B1 (fr)	1985-02-13	Nouveaux fongicides homologués des N-phényl alaninates et leur procédé de préparation et leur application
EP0249567A2 (fr)	1987-12-16	Dérivés propargyloxybenzènes, leur préparation et compositions fongicides les contenant
FR2543142A1 (fr)	1984-09-28	Ester de l'hydroxyde de tricyclohexyletain acaricide
CH633781A5 (fr)	1982-12-31	Derives de l'oxadiazole-1,3,4 utilisables comme fongicides.
EP0097107B1 (fr)	1985-09-18	Nouveaux dérivés de l'acide phénylimino-2 acétique, leur préparation et leur utilisation comme régulateurs de la croissance des plantes
EP0016132A1 (fr)	1980-10-01	Nouvelle phenyluree substituee herbicide
LU86116A1 (fr)	1986-03-24	Compositions herbicides selectives ayant une action prolongee et contenant,a titre d'ingredient actif,des derives d'alpha-chloracetamide
EP0246984A2 (fr)	1987-11-25	Herbicides de type sulfonylurée, leur préparation, les compositions les contenant et leur utilisation
FR2549839A1 (fr)	1985-02-01	Nouveaux herbicides a groupe sulfonamide derives de la n-phosphonomethyl glycine
LU80635A1 (fr)	1980-07-21	Nouveaux derives de ureido-3(thio)chromones et compositions herbicides les contenant
FR2486938A1 (fr)	1982-01-22	Nouveaux derives de la dihydro-1, 4 pyridine, leur preparation et leur application pour le desherbage selectif de cultures