CA1090367A - Derives des acides phenoxyphenoxyalcanecarboxyliques comme regulateurs de croissance vegetale - Google Patents

Derives des acides phenoxyphenoxyalcanecarboxyliques comme regulateurs de croissance vegetale

Info

Publication number: CA1090367A
Authority: CA; Canada
Prior art keywords: formula; radical; halogen; cyano; substituted
Prior art date: 1977-06-30
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA306,425A

Other languages

English (en)

Inventor

Otto Rohr

Georg Pissiotas

Dieter Durr

Beat Bohner

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Novartis AG

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.)

1977-06-30

Filing date

1978-06-28

Publication date

1980-11-25

1978-06-28 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1980-11-25 Application granted granted Critical

1980-11-25 Publication of CA1090367A publication Critical patent/CA1090367A/fr

Status Expired legal-status Critical Current

Links

239000002253 acid Substances 0.000 title claims abstract description 13
230000008635 plant growth Effects 0.000 title claims abstract description 8
230000001105 regulatory effect Effects 0.000 title claims abstract description 5
230000002363 herbicidal effect Effects 0.000 title abstract description 12
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 37
150000001875 compounds Chemical class 0.000 claims abstract description 32
-1 cyano, carboxyl Chemical group 0.000 claims abstract description 22
229910052736 halogen Inorganic materials 0.000 claims abstract description 18
150000002367 halogens Chemical class 0.000 claims abstract description 18
239000001257 hydrogen Substances 0.000 claims abstract description 18
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 17
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 10
150000002431 hydrogen Chemical class 0.000 claims abstract description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 6
241000196324 Embryophyta Species 0.000 claims description 40
239000000203 mixture Substances 0.000 claims description 19
150000003254 radicals Chemical class 0.000 claims description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
238000000034 method Methods 0.000 claims description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
239000005864 Sulphur Substances 0.000 claims description 5
150000001768 cations Chemical class 0.000 claims description 5
230000001276 controlling effect Effects 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 3
150000001340 alkali metals Chemical class 0.000 claims description 3
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
239000002585 base Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 3
125000003342 alkenyl group Chemical group 0.000 claims 2
RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 claims 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
230000002401 inhibitory effect Effects 0.000 abstract description 7
230000009471 action Effects 0.000 abstract description 6
150000001408 amides Chemical class 0.000 abstract 1
150000001734 carboxylic acid salts Chemical class 0.000 abstract 1
150000002148 esters Chemical class 0.000 abstract 1
150000007970 thio esters Chemical class 0.000 abstract 1
239000000460 chlorine Substances 0.000 description 53
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 47
239000013543 active substance Substances 0.000 description 31
230000012010 growth Effects 0.000 description 19
239000003921 oil Substances 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
244000025254 Cannabis sativa Species 0.000 description 7
235000013339 cereals Nutrition 0.000 description 7
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 7
239000002904 solvent Substances 0.000 description 7
239000005995 Aluminium silicate Substances 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
241000209504 Poaceae Species 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
235000012211 aluminium silicate Nutrition 0.000 description 6
229910052801 chlorine Inorganic materials 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
239000011541 reaction mixture Substances 0.000 description 6
244000068988 Glycine max Species 0.000 description 5
235000010469 Glycine max Nutrition 0.000 description 5
244000061176 Nicotiana tabacum Species 0.000 description 5
235000002637 Nicotiana tabacum Nutrition 0.000 description 5
238000009472 formulation Methods 0.000 description 5
239000008187 granular material Substances 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
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239000002689 soil Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
238000009835 boiling Methods 0.000 description 4
235000013399 edible fruits Nutrition 0.000 description 4
238000003306 harvesting Methods 0.000 description 4
239000004009 herbicide Substances 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
229920000151 polyglycol Polymers 0.000 description 4
239000010695 polyglycol Substances 0.000 description 4
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000000843 powder Substances 0.000 description 4
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
241000252254 Catostomidae Species 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000002202 Polyethylene glycol Substances 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
240000000111 Saccharum officinarum Species 0.000 description 3
235000007201 Saccharum officinarum Nutrition 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
239000000969 carrier Substances 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
238000005520 cutting process Methods 0.000 description 3
235000021186 dishes Nutrition 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
230000035784 germination Effects 0.000 description 3
230000009036 growth inhibition Effects 0.000 description 3
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 3
239000003960 organic solvent Substances 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
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
239000000376 reactant Substances 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
244000291564 Allium cepa Species 0.000 description 2
235000002732 Allium cepa var. cepa Nutrition 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
240000005979 Hordeum vulgare Species 0.000 description 2
235000007340 Hordeum vulgare Nutrition 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
241000209056 Secale Species 0.000 description 2
244000061456 Solanum tuberosum Species 0.000 description 2
235000002595 Solanum tuberosum Nutrition 0.000 description 2
244000098338 Triticum aestivum Species 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
239000000470 constituent Substances 0.000 description 2
239000004495 emulsifiable concentrate Substances 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
239000003966 growth inhibitor Substances 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
239000005457 ice water Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
ACEONLNNWKIPTM-UHFFFAOYSA-N methyl 2-bromopropanoate Chemical compound COC(=O)C(C)Br ACEONLNNWKIPTM-UHFFFAOYSA-N 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
239000004033 plastic Substances 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
230000008569 process Effects 0.000 description 2
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
238000009331 sowing Methods 0.000 description 2
239000007921 spray Substances 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
125000006569 (C5-C6) heterocyclic group Chemical group 0.000 description 1
BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical group [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 1
JEANOXXXGPLTOI-UHFFFAOYSA-N 2,4,4-trimethyl cyclo hexanone Natural products CC1CC(C)(C)CCC1=O JEANOXXXGPLTOI-UHFFFAOYSA-N 0.000 description 1
OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
IULJSGIJJZZUMF-UHFFFAOYSA-N 2-hydroxybenzenesulfonic acid Chemical compound OC1=CC=CC=C1S(O)(=O)=O IULJSGIJJZZUMF-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
240000004585 Dactylis glomerata Species 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
241000220485 Fabaceae Species 0.000 description 1
241000410074 Festuca ovina Species 0.000 description 1
240000004296 Lolium perenne Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000207836 Olea <angiosperm> Species 0.000 description 1
241000209049 Poa pratensis Species 0.000 description 1
238000000297 Sandmeyer reaction Methods 0.000 description 1
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
235000021307 Triticum Nutrition 0.000 description 1
241000358324 Viverricula indica Species 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
229940115440 aluminum sodium silicate Drugs 0.000 description 1
230000003698 anagen phase Effects 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Chemical group 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
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235000019993 champagne Nutrition 0.000 description 1
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125000001309 chloro group Chemical group Cl* 0.000 description 1
235000020971 citrus fruits Nutrition 0.000 description 1
239000007931 coated granule Substances 0.000 description 1
238000012505 colouration Methods 0.000 description 1
230000035613 defoliation Effects 0.000 description 1
238000007865 diluting Methods 0.000 description 1
229960001760 dimethyl sulfoxide Drugs 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000000428 dust Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000003628 erosive effect Effects 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
230000035558 fertility Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
230000028245 fruit abscission Effects 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
238000000227 grinding Methods 0.000 description 1
125000001841 imino group Chemical group [H]N=* 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
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150000007529 inorganic bases Chemical class 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
230000028514 leaf abscission Effects 0.000 description 1
239000012669 liquid formulation Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
235000009973 maize Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
230000000802 nitrating effect Effects 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 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
150000007530 organic bases Chemical class 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000006072 paste Substances 0.000 description 1
239000000441 potassium aluminium silicate Substances 0.000 description 1
235000012219 potassium aluminium silicate Nutrition 0.000 description 1
235000012015 potatoes Nutrition 0.000 description 1
230000009290 primary effect Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
239000004576 sand Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000004904 shortening Methods 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000000429 sodium aluminium silicate Substances 0.000 description 1
235000012217 sodium aluminium silicate Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 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
IZWPGJFSBABFGL-GMFCBQQYSA-M sodium;2-[methyl-[(z)-octadec-9-enoyl]amino]ethanesulfonate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CCS([O-])(=O)=O IZWPGJFSBABFGL-GMFCBQQYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/39—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups
- C07C205/42—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups having nitro groups or esterified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/43—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups having nitro groups or esterified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- 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
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
- A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/38—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. nitrodiphenyl ethers
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids

Landscapes

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

CA306,425A 1977-06-30 1978-06-28 Derives des acides phenoxyphenoxyalcanecarboxyliques comme regulateurs de croissance vegetale Expired CA1090367A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH8068/77		1977-06-30
CH806877		1977-06-30

Publications (1)

Publication Number	Publication Date
CA1090367A true CA1090367A (fr)	1980-11-25

Family

ID=4334639

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA306,425A Expired CA1090367A (fr)	1977-06-30	1978-06-28	Derives des acides phenoxyphenoxyalcanecarboxyliques comme regulateurs de croissance vegetale

Country Status (7)

Country	Link
EP (1)	EP0000474B1 (fr)
JP (1)	JPS5416436A (fr)
CA (1)	CA1090367A (fr)
DE (1)	DE2860339D1 (fr)
ES (1)	ES471398A1 (fr)
IL (1)	IL55029A (fr)
IT (1)	IT7825138A0 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2850902A1 (de) *	1978-11-24	1980-06-12	Hoechst Ag	Neue phenoxy-phenoxi-propionsaeureamide und ihre verwendung als herbizide
US4309210A (en) *	1978-12-01	1982-01-05	Ciba-Geigy Corporation	Preemergence method of selectively controlling weeds in crops of cereals and composition therefor
EP0078536A3 (fr) *	1981-11-02	1983-07-27	Sandoz Ag	Phosphinates et phosphonates et leur utilisation comme herbicides

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1560416A (en) *	1975-09-03	1980-02-06	Rohm & Haas	Trifluoromethylphenyl derivatives
NZ181994A (en) *	1975-09-27	1978-09-20	Ishihara Sangyo Kaisha	(2-chloro-4-trifluorom-ethylphenoxy)-phenoxy acids,esters,ethers,amides and nitriles and herbicidal compositions
GB1565972A (en) *	1976-04-15	1980-04-23	Sori Soc Rech Ind	M-substituted phenoxypropionic acid dervatives
DE2632581C2 (de) *	1976-07-20	1982-07-15	Hoechst Ag, 6000 Frankfurt	Substituierte Nitrodiphenylether, Verfahren zu ihrer Herstellung und diese enthaltende herbizide Mittel
AU2716177A (en) *	1976-07-21	1979-01-25	Ciba Geigy Ag	Herbicides

1978
- 1978-06-22 DE DE7878100218T patent/DE2860339D1/de not_active Expired
- 1978-06-22 EP EP78100218A patent/EP0000474B1/fr not_active Expired
- 1978-06-28 CA CA306,425A patent/CA1090367A/fr not_active Expired
- 1978-06-28 IL IL55029A patent/IL55029A/xx unknown
- 1978-06-29 ES ES471398A patent/ES471398A1/es not_active Expired
- 1978-06-29 IT IT7825138A patent/IT7825138A0/it unknown
- 1978-06-30 JP JP8044678A patent/JPS5416436A/ja active Pending

Also Published As

Publication number	Publication date
DE2860339D1 (en)	1981-02-12
EP0000474A1 (fr)	1979-02-07
EP0000474B1 (fr)	1980-11-26
IT7825138A0 (it)	1978-06-29
IL55029A (en)	1982-09-30
IL55029A0 (en)	1978-08-31
JPS5416436A (en)	1979-02-07
ES471398A1 (es)	1979-02-01

Legal Events

Date	Code	Title	Description
1997-11-25	MKEX	Expiry

Publication	Publication Date	Title
US4349377A (en)	1982-09-14	Phenoxyphenylthioalkanecarboxylic acid amides and their use as herbicides and plant growth regulants
CA1100964A (fr)	1981-05-12	Traduction non-disponible
US4332961A (en)	1982-06-01	Herbicidal compound, herbicidal composition containing the same, and method of use thereof
CA1110245A (fr)	1981-10-06	Acides phenoxy-valeriques et leurs derives, utilises comme herbicide
CA1101867A (fr)	1981-05-26	Traduction non-disponible
KR820001834B1 (ko)	1982-10-13	피리딜옥시-페녹시-a프로피온산 아미노알킬 에스테르의 제조방법
US4391624A (en)	1983-07-05	Herbicidally active 2-substituted 5-phenoxyphenylphosphonic acid esters
CA1083574A (fr)	1980-08-12	Derives des acides 1-(bis-trifluoromethylphenyl)-2- oxo-pyrrolidine-4-carboxyliques, leur production et leur emploi comme regulateurs de la croissance vegetale et comme herbicides
JPS6353176B2 (fr)	1988-10-21
JPH0657684B2 (ja)	1994-08-03	Ｎ―ベンジル２―（４―フルオル―３―トリフルオルメチルフェノキシ）ブタン酸アミド及びそれを含有する除草剤
US4304936A (en)	1981-12-08	Herbicidal 3-(trifluro-methyl-halophenoxy)-α-phenoxyalkanecarboxylic acid amides
CA1179337A (fr)	1984-12-11	Derives de trifluoromethyl-phenoxy-phenyl-silicone, procede de prepartion et utilisation comme herbicides et regulateurs de la croissance des plantes
CA1091240A (fr)	1980-12-09	Derives de l'acide phenoxy-phenoxy-alcanecarboxylique ayant une action herbicide, production desdits derives, composes les contenant et utilisation
US4945113A (en)	1990-07-31	herbicidal sulfonamide derivatives
CA1090367A (fr)	1980-11-25	Derives des acides phenoxyphenoxyalcanecarboxyliques comme regulateurs de croissance vegetale
CA1240705A (fr)	1988-08-16	N-(1'-methyl-2'-methoxyethyl)-n-chloro-2,6- dimethyl-aniline optiquement active, agent herbicides
US4092151A (en)	1978-05-30	Herbicidal compound, herbicidal composition containing the same and method of use thereof
CA1153008A (fr)	1983-08-30	Derives d'acide phenoxy-phenoxy-alcanecarboxylique ayant des proprietes herbicides, et utilisation pour les mauvaises herbes
US4429146A (en)	1984-01-31	Substituted diphenyl ether herbicides and process for use
US4221581A (en)	1980-09-09	Phenoxyphenoxyalkanecarboxylic acid esters
EP0034012A2 (fr)	1981-08-19	Dérivés de la 2-nitro 5(phénoxy substitué) phénylalcanone-oxime et -imine utilisés comme herbicides
CA1127161A (fr)	1982-07-06	Phenoxyalkyloxazolines
CA1080746A (fr)	1980-07-01	Derives d'acide hydroxamique comme regulateurs de la croissange vegetale
CA1102818A (fr)	1981-06-09	Traduction non-disponible
US4434108A (en)	1984-02-28	Herbicidally active 2-nitro-5-(2'-chloro-4'-trifluoromethylphenoxy)phenylphosphinic acid derivatives