HU180918B - Plant growth regulating and herbicide compositions containing thiophene-2-carboxamide-oxime derivatives as active substances and process for preparing the active substances - Google Patents

Plant growth regulating and herbicide compositions containing thiophene-2-carboxamide-oxime derivatives as active substances and process for preparing the active substances Download PDF

Info

Publication number: HU180918B
Authority: HU; Hungary
Prior art keywords: formula; compound; active substances; iii; alkyl
Prior art date: 1977-07-28

Application number

HU78PI633A

Other languages

English (en)

Hungarian (hu)

Inventor

Daniel Farge

Jean Leboul

Goff Yves Le

Gilbert Poigert

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

1983-05-30

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

1983-05-30 Publication of HU180918B publication Critical patent/HU180918B/hu

Links

239000000203 mixture Substances 0.000 title claims description 28
230000002363 herbicidal effect Effects 0.000 title claims description 9
NKMNPRXPUZINOM-UHFFFAOYSA-N n'-hydroxythiophene-2-carboximidamide Chemical class ON=C(N)C1=CC=CS1 NKMNPRXPUZINOM-UHFFFAOYSA-N 0.000 title claims description 7
239000004009 herbicide Substances 0.000 title abstract description 4
230000008635 plant growth Effects 0.000 title description 3
230000001105 regulatory effect Effects 0.000 title description 3
238000004519 manufacturing process Methods 0.000 title description 2
239000013543 active substance Substances 0.000 title 2
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 5
150000001875 compounds Chemical class 0.000 claims description 43
125000000217 alkyl group Chemical group 0.000 claims description 18
238000002360 preparation method Methods 0.000 claims description 15
239000003795 chemical substances by application Substances 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
-1 halogen nitrile Chemical class 0.000 claims description 6
238000000034 method Methods 0.000 claims description 6
239000007787 solid Substances 0.000 claims description 6
239000007788 liquid Substances 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
239000004094 surface-active agent Substances 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
229920002125 Sokalan® Polymers 0.000 claims description 2
229920005610 lignin Polymers 0.000 claims description 2
239000004584 polyacrylic acid Substances 0.000 claims description 2
CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 claims 2
206010029897 Obsessive thoughts Diseases 0.000 claims 1
239000002635 aromatic organic solvent Substances 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
229910052500 inorganic mineral Inorganic materials 0.000 claims 1
239000011707 mineral Substances 0.000 claims 1
239000005648 plant growth regulator Substances 0.000 claims 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
125000004432 carbon atom Chemical group C* 0.000 abstract description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 4
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical class [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
229930195732 phytohormone Natural products 0.000 abstract 1
239000004480 active ingredient Substances 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
241000196324 Embryophyta Species 0.000 description 13
239000000243 solution Substances 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
229920003023 plastic Polymers 0.000 description 8
239000004033 plastic Substances 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
229940125904 compound 1 Drugs 0.000 description 7
238000012360 testing method Methods 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
238000009472 formulation Methods 0.000 description 6
239000002904 solvent Substances 0.000 description 6
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
241000209140 Triticum Species 0.000 description 5
239000013078 crystal Substances 0.000 description 5
235000013399 edible fruits Nutrition 0.000 description 5
239000000839 emulsion Substances 0.000 description 5
125000001424 substituent group Chemical group 0.000 description 5
239000000080 wetting agent 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
235000007688 Lycopersicon esculentum Nutrition 0.000 description 4
240000003768 Solanum lycopersicum Species 0.000 description 4
235000021307 Triticum Nutrition 0.000 description 4
239000000853 adhesive Substances 0.000 description 4
230000001070 adhesive effect Effects 0.000 description 4
239000000047 product Substances 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
239000002689 soil Substances 0.000 description 4
238000005507 spraying Methods 0.000 description 4
239000003381 stabilizer Substances 0.000 description 4
239000004563 wettable powder Substances 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
244000043158 Lens esculenta Species 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000000654 additive Substances 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
235000008504 concentrate Nutrition 0.000 description 3
239000002270 dispersing agent Substances 0.000 description 3
239000006185 dispersion 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
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
241000335053 Beta vulgaris Species 0.000 description 2
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
235000014647 Lens culinaris subsp culinaris Nutrition 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
241000220259 Raphanus Species 0.000 description 2
244000088415 Raphanus sativus Species 0.000 description 2
235000011380 Raphanus sativus Nutrition 0.000 description 2
235000006140 Raphanus sativus var sativus Nutrition 0.000 description 2
235000021536 Sugar beet Nutrition 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
230000000996 additive effect Effects 0.000 description 2
125000004414 alkyl thio group Chemical group 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
230000008033 biological extinction Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000000084 colloidal system Substances 0.000 description 2
239000003086 colorant Substances 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
229940125782 compound 2 Drugs 0.000 description 2
238000005260 corrosion Methods 0.000 description 2
230000007797 corrosion Effects 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
239000004495 emulsifiable concentrate Substances 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
230000003054 hormonal effect Effects 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
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
230000035515 penetration Effects 0.000 description 2
230000000361 pesticidal effect Effects 0.000 description 2
239000000843 powder Substances 0.000 description 2
230000001681 protective effect Effects 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
239000007921 spray Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
230000004936 stimulating effect Effects 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000004546 suspension concentrate Substances 0.000 description 2
CDOUZKKFHVEKRI-UHFFFAOYSA-N 3-bromo-n-[(prop-2-enoylamino)methyl]propanamide Chemical compound BrCCC(=O)NCNC(=O)C=C CDOUZKKFHVEKRI-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
241001621841 Alopecurus myosuroides Species 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
235000016068 Berberis vulgaris Nutrition 0.000 description 1
235000021533 Beta vulgaris Nutrition 0.000 description 1
RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
241001327343 Chrysopogon gryllus Species 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
241000219739 Lens Species 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
240000000111 Saccharum officinarum Species 0.000 description 1
235000007201 Saccharum officinarum Nutrition 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
244000098338 Triticum aestivum Species 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000004442 acylamino group Chemical group 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
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 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
230000003373 anti-fouling effect Effects 0.000 description 1
239000002518 antifoaming agent Substances 0.000 description 1
239000002519 antifouling agent Substances 0.000 description 1
239000007798 antifreeze agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
229920005551 calcium lignosulfonate Polymers 0.000 description 1
RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
238000001514 detection method Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
239000012153 distilled water 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
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000010410 dusting Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000011389 fruit/vegetable juice Nutrition 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
239000003864 humus Substances 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000005286 illumination Methods 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
230000000749 insecticidal effect Effects 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
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000000155 melt Substances 0.000 description 1
229910052751 metal Chemical group 0.000 description 1
239000002184 metal Chemical group 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
229920000847 nonoxynol Polymers 0.000 description 1
229940049964 oleate Drugs 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
230000000149 penetrating effect Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical class OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 1
239000003375 plant hormone Substances 0.000 description 1
235000014483 powder concentrate Nutrition 0.000 description 1
239000002244 precipitate Substances 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
238000004062 sedimentation Methods 0.000 description 1
239000003352 sequestering agent Substances 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
238000012549 training Methods 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000001993 wax Substances 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)

HU78PI633A 1977-07-28 1978-07-28 Plant growth regulating and herbicide compositions containing thiophene-2-carboxamide-oxime derivatives as active substances and process for preparing the active substances HU180918B (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
HU180918B true HU180918B (en)	1983-05-30

Family

ID=9194251

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU78PI633A HU180918B (en)	1977-07-28	1978-07-28	Plant growth regulating and herbicide compositions containing thiophene-2-carboxamide-oxime derivatives as active substances and process for preparing the active substances

Country Status (18)

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

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/fr active

Also Published As

Publication number	Publication date
FR2398744B2 (fr)	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
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
CH634067A5 (en)	1983-01-14
ES472090A2 (es)	1979-10-16

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SU1665875A3 (ru)	1991-07-23	Способ получени Е-изомеров производных акриловой кислоты
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US4066436A (en)	1978-01-03	Method of controlling sicklepod in soybeans
EP0046069A1 (fr)	1982-02-17	Diphényl-pyridazinones herbicides et régulateurs de la croissance des plantes
US4188203A (en)	1980-02-12	Herbicidal and phytohormonal amidoximes
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HU180918B (en)	1983-05-30	Plant growth regulating and herbicide compositions containing thiophene-2-carboxamide-oxime derivatives as active substances and process for preparing the active substances
HU176418B (en)	1981-02-28	Hormonal and herbicide compositions for plant containing 1,2,4-oxadiazin-5-one,and process for producing this compound
USRE29439E (en)	1977-10-11	Certain 1,2,4-Oxa- and -thiadiazol-5-ylthioalkanoic acid derivatives
SU867280A3 (ru)	1981-09-23	Средство дл регулировани роста растений
JPS6038370A (ja)	1985-02-27	新規な複素環置換スルホニル尿素、それらの製造方法およびそれらを含有する除草剤または植物生長調整剤
CS214799B2 (cs)	1982-05-28	Prostředek k regulaci růstu rostlin a způsob výroby účinných látek
KR790001934B1 (ko)	1979-12-29	신규한 아미독심 유도체의 제조법
US4338118A (en)	1982-07-06	Plant growth regulation
US4217459A (en)	1980-08-12	Benzylthio-1,3,4-thiadiazol-2-yl ureas
KR810001506B1 (ko)	1981-10-25	3-우레이도-(티오)-크로몬 유도체의 제조방법
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KR800000625B1 (ko)	1980-07-07	아닐린 유도체의 제조방법
KR800001639B1 (ko)	1980-12-31	1, 2, 3-티아디아졸린-2-이드 유도체의 제조방법