CH623986A5 - Herbicide and its use for the selective control of grass weeds - Google Patents

Herbicide and its use for the selective control of grass weeds Download PDF

Info

Publication number: CH623986A5
Authority: CH; Switzerland
Prior art keywords: sep; formula; phenoxy; group; alkyl
Prior art date: 1975-11-20

Application number

CH1503375A

Other languages

German (de)

English (en)

Inventor

Otto Dr Rohr

Beat Dr Boehner

Georg Dr Pissiotas

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.)

1975-11-20

Filing date

1975-11-20

Publication date

1981-07-15

1975-11-20 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1975-11-20 Priority to CH1503375A priority Critical patent/CH623986A5/de

1976-11-16 Priority to US05/742,311 priority patent/US4106925A/en

1976-11-17 Priority to IL50928A priority patent/IL50928A/xx

1976-11-17 Priority to FR7634607A priority patent/FR2332258A1/fr

1976-11-17 Priority to DE19762652384 priority patent/DE2652384A1/de

1976-11-18 Priority to NL7612858A priority patent/NL7612858A/xx

1976-11-18 Priority to CA266,072A priority patent/CA1103696A/fr

1976-11-19 Priority to ES453463A priority patent/ES453463A1/es

1976-11-19 Priority to BE172506A priority patent/BE848526A/fr

1976-11-19 Priority to GB48354/76A priority patent/GB1563610A/en

1976-11-19 Priority to JP51139402A priority patent/JPS5265238A/ja

1978-06-14 Priority to US05/915,491 priority patent/US4205978A/en

1978-07-19 Priority to US05/926,061 priority patent/US4183743A/en

1978-07-19 Priority to US05/926,162 priority patent/US4193790A/en

1981-07-15 Publication of CH623986A5 publication Critical patent/CH623986A5/de

Links

230000002363 herbicidal effect Effects 0.000 title claims abstract description 17
239000004009 herbicide Substances 0.000 title claims abstract description 9
241001148683 Zostera marina Species 0.000 title abstract description 3
241000196324 Embryophyta Species 0.000 claims abstract description 26
125000000217 alkyl group Chemical group 0.000 claims abstract description 24
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
239000001257 hydrogen Substances 0.000 claims abstract description 19
239000000203 mixture Substances 0.000 claims abstract description 15
235000010469 Glycine max Nutrition 0.000 claims abstract description 11
241000209140 Triticum Species 0.000 claims abstract description 11
235000021307 Triticum Nutrition 0.000 claims abstract description 11
229910052736 halogen Inorganic materials 0.000 claims abstract description 11
150000002367 halogens Chemical group 0.000 claims abstract description 11
244000068988 Glycine max Species 0.000 claims abstract description 10
239000002253 acid Substances 0.000 claims abstract description 10
150000002431 hydrogen Chemical class 0.000 claims abstract description 10
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 claims abstract description 9
229920000742 Cotton Polymers 0.000 claims abstract description 9
235000021536 Sugar beet Nutrition 0.000 claims abstract description 9
235000007320 Avena fatua Nutrition 0.000 claims abstract description 7
238000000034 method Methods 0.000 claims abstract description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
238000002360 preparation method Methods 0.000 claims abstract description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 38
239000004480 active ingredient Substances 0.000 claims description 31
239000003795 chemical substances by application Substances 0.000 claims description 28
150000001875 compounds Chemical class 0.000 claims description 13
-1 benzyloxy, phenoxy Chemical group 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
241000209764 Avena fatua Species 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
BNJMRELGMDUDDB-UHFFFAOYSA-N $l^{1}-sulfanylbenzene Chemical compound [S]C1=CC=CC=C1 BNJMRELGMDUDDB-UHFFFAOYSA-N 0.000 claims description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
244000038559 crop plants Species 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 3
KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical group O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims description 3
YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 2
DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical class C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
244000299507 Gossypium hirsutum Species 0.000 claims 1
241000219146 Gossypium Species 0.000 abstract description 9
239000013543 active substance Substances 0.000 abstract description 7
241000209510 Liliopsida Species 0.000 abstract description 4
244000075850 Avena orientalis Species 0.000 abstract description 3
235000005373 Uvularia sessilifolia Nutrition 0.000 abstract description 2
150000001298 alcohols Chemical class 0.000 abstract description 2
241001233957 eudicotyledons Species 0.000 abstract description 2
WSZIZZNQVNLVOK-UHFFFAOYSA-N 2-[4-(2-chloro-3-nitrophenoxy)phenoxy]propanoic acid Chemical class C1=CC(OC(C)C(O)=O)=CC=C1OC1=CC=CC([N+]([O-])=O)=C1Cl WSZIZZNQVNLVOK-UHFFFAOYSA-N 0.000 abstract 1
241001330028 Panicoideae Species 0.000 abstract 1
239000003921 oil Substances 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
239000000839 emulsion Substances 0.000 description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
241000209219 Hordeum Species 0.000 description 6
239000008187 granular material Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
239000005995 Aluminium silicate Substances 0.000 description 5
235000007340 Hordeum vulgare Nutrition 0.000 description 5
241000209094 Oryza Species 0.000 description 5
235000012211 aluminium silicate Nutrition 0.000 description 5
239000002585 base Substances 0.000 description 5
125000004432 carbon atom Chemical group C* 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
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
235000007164 Oryza sativa Nutrition 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
229920000151 polyglycol Polymers 0.000 description 4
239000010695 polyglycol Substances 0.000 description 4
235000009566 rice Nutrition 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
241000743985 Alopecurus Species 0.000 description 3
235000017896 Digitaria Nutrition 0.000 description 3
241001303487 Digitaria <clam> Species 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
150000001768 cations Chemical class 0.000 description 3
235000013339 cereals Nutrition 0.000 description 3
238000006243 chemical reaction Methods 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
150000003254 radicals Chemical class 0.000 description 3
239000000725 suspension Substances 0.000 description 3
239000004563 wettable powder Substances 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
241001666377 Apera Species 0.000 description 2
235000004535 Avena sterilis Nutrition 0.000 description 2
244000025254 Cannabis sativa Species 0.000 description 2
241000192043 Echinochloa Species 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
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
241000209082 Lolium Species 0.000 description 2
241000209504 Poaceae Species 0.000 description 2
241000857233 Rottboellia Species 0.000 description 2
UUTFFHNHMRSARV-UHFFFAOYSA-N Setarin Chemical compound C1=CC=CC2=C1OC(=O)C=C2OC(=C)C UUTFFHNHMRSARV-UHFFFAOYSA-N 0.000 description 2
244000062793 Sorghum vulgare Species 0.000 description 2
240000008042 Zea mays Species 0.000 description 2
235000002017 Zea mays subsp mays Nutrition 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
239000004495 emulsifiable concentrate Substances 0.000 description 2
150000002148 esters Chemical group 0.000 description 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Natural products O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000843 powder Substances 0.000 description 2
LWRKLYVFSHDLMU-UHFFFAOYSA-N setarin Natural products C1=CC=CC2=C1OC(=O)C=C2OCC=C LWRKLYVFSHDLMU-UHFFFAOYSA-N 0.000 description 2
239000000243 solution Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
NTBYINQTYWZXLH-UHFFFAOYSA-N 1,2-dichloro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(Cl)=C1 NTBYINQTYWZXLH-UHFFFAOYSA-N 0.000 description 1
ZSBDGXGICLIJGD-UHFFFAOYSA-N 4-phenoxyphenol Chemical class C1=CC(O)=CC=C1OC1=CC=CC=C1 ZSBDGXGICLIJGD-UHFFFAOYSA-N 0.000 description 1
241000743339 Agrostis Species 0.000 description 1
240000007087 Apium graveolens Species 0.000 description 1
235000015849 Apium graveolens Dulce Group Nutrition 0.000 description 1
235000010591 Appio Nutrition 0.000 description 1
235000007319 Avena orientalis Nutrition 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
241000219112 Cucumis Species 0.000 description 1
235000015510 Cucumis melo subsp melo Nutrition 0.000 description 1
240000008067 Cucumis sativus Species 0.000 description 1
235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
244000058871 Echinochloa crus-galli Species 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
235000009438 Gossypium Nutrition 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
240000004658 Medicago sativa Species 0.000 description 1
235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 1
244000061176 Nicotiana tabacum Species 0.000 description 1
235000002637 Nicotiana tabacum Nutrition 0.000 description 1
IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
235000011999 Panicum crusgalli Nutrition 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
240000001451 Rottboellia cochinchinensis Species 0.000 description 1
241000209056 Secale Species 0.000 description 1
235000007238 Secale cereale Nutrition 0.000 description 1
235000005775 Setaria Nutrition 0.000 description 1
241000232088 Setaria <nematode> Species 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 1
241000219793 Trifolium Species 0.000 description 1
241000209149 Zea Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
125000003302 alkenyloxy group Chemical group 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
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
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000000969 carrier Substances 0.000 description 1
235000019993 champagne Nutrition 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000000470 constituent Substances 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
150000002170 ethers Chemical class 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
239000000417 fungicide Substances 0.000 description 1
230000001408 fungistatic effect Effects 0.000 description 1
238000000227 grinding Methods 0.000 description 1
150000003977 halocarboxylic acids Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000002917 insecticide 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
235000021374 legumes Nutrition 0.000 description 1
239000007788 liquid Substances 0.000 description 1
235000009973 maize Nutrition 0.000 description 1
235000019713 millet Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000001069 nematicidal effect Effects 0.000 description 1
239000005645 nematicide Substances 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-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
239000003960 organic solvent Substances 0.000 description 1
239000006072 paste Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/59—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
- C07C205/60—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms in ortho-position to the carboxyl group, e.g. nitro-salicylic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/59—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH1503375A 1975-11-20 1975-11-20 Herbicide and its use for the selective control of grass weeds CH623986A5 (en)

Priority Applications (14)

Application Number	Priority Date	Filing Date	Title
CH1503375A CH623986A5 (en)	1975-11-20	1975-11-20	Herbicide and its use for the selective control of grass weeds
US05/742,311 US4106925A (en)	1975-11-20	1976-11-16	Novel herbicidally active, nuclear-substituted phenoxy-phenoxy-alkanecarboxylic acid derivatives and use thereof for controlling grass-like weeds
IL50928A IL50928A (en)	1975-11-20	1976-11-17	Nitro phenoxy-phenoxy-alkanecarboxylic acid derivatives,their preparation and herbicidal compositions containing them
FR7634607A FR2332258A1 (fr)	1975-11-20	1976-11-17	Nouveaux derives d'acides phenoxy-phenoxy-alcanecarboxyliques a activite herbicide et leur application dans la lutte contre les mauvaises herbes
DE19762652384 DE2652384A1 (de)	1975-11-20	1976-11-17	Neue herbizid wirksame, kernsubstituierte phenoxy-phenoxy-alkancarbonsaeurederivate und deren verwendung zur bekaempfung von ungraesern
NL7612858A NL7612858A (nl)	1975-11-20	1976-11-18	Nieuwe als herbicide werkzame, in de kern gesub- stitueerde fenoxy-fenoxyalkaancarbonzuurderiva- ten en de toepassing ervan voor het bestrijden van grasachtige onkruiden.
CA266,072A CA1103696A (fr)	1975-11-20	1976-11-18	Derives herbicides d'acides phenoxy-phenoxy- alcanecarboxyliques a substitution sur le noyau; emploi contre les mauvaises herbes
ES453463A ES453463A1 (es)	1975-11-20	1976-11-19	Procedimiento para la preparacion de nuevos derivados de acido 4-fenoxi-alfa-fenoxi alcancarboxilico de accion herbi-cida.
BE172506A BE848526A (fr)	1975-11-20	1976-11-19	Nouveaux derives d'acides phenoxy-alcanecarboxyliques a activite herbicide et leur application dans la lutte contes les mauvaises herbes,
GB48354/76A GB1563610A (en)	1975-11-20	1976-11-19	Herbicidally active nuclear-substituted phenoxy-phenoxy-alkanecarboxylic acid derivatives and use thereof for controlling grass-like weeds
JP51139402A JPS5265238A (en)	1975-11-20	1976-11-19	Nucleusssubstited phenoxyyphenoxyy alkane carboxylic acid derivatives* process for producing same and herbicide containing said compound
US05/915,491 US4205978A (en)	1975-11-20	1978-06-14	Novel herbicidally active, nuclear-substituted phenoxy-phenoxyalkanecarboxylic acid derivatives and use thereof for controlling grass-like weeds
US05/926,061 US4183743A (en)	1975-11-20	1978-07-19	Novel herbicidally active, nuclear-substituted phenoxy-phenoxy-alkanecarboxylic acid derivatives and use thereof for controlling grass-like weeds
US05/926,162 US4193790A (en)	1975-11-20	1978-07-19	Novel herbicidally active, nuclear-substituted phenoxy-phenoxy-alkanecarboxylic acid derivatives and use thereof for controlling grass-like weeds

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1503375A CH623986A5 (en)	1975-11-20	1975-11-20	Herbicide and its use for the selective control of grass weeds

Publications (1)

Publication Number	Publication Date
CH623986A5 true CH623986A5 (en)	1981-07-15

Family

ID=4405758

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1503375A CH623986A5 (en)	1975-11-20	1975-11-20	Herbicide and its use for the selective control of grass weeds

Country Status (2)

Country	Link
BE (1)	BE848526A (fr)
CH (1)	CH623986A5 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4192669A (en) *	1977-12-22	1980-03-11	E. I. Du Pont De Nemours And Company	Herbicidal ethers

1975
- 1975-11-20 CH CH1503375A patent/CH623986A5/de not_active IP Right Cessation
1976
- 1976-11-19 BE BE172506A patent/BE848526A/fr unknown

Also Published As

Publication number	Publication date
BE848526A (fr)	1977-05-20

Legal Events

Date	Code	Title	Description
1984-07-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
EP0003114B1 (fr)	1982-01-27	Esters insaturés à activité herbicide d'acides 4- (3',5'-dihalogéno-pyridyl -(2')-oxy)-alpha-phénoxypropionique, procédé de leur préparation, compositions herbicides les contenant et leur utilisation
EP0000351A1 (fr)	1979-01-24	Dérivés d'acides phénoxy-phenyl-thio-alkylcarboxyliques, méthode de préparation et leur application comme herbicides et régulateurs de croissance des plantes
DE2433067B2 (de)	1977-11-24	Alpha- eckige klammer auf 4-(4' trifluormethylphenoxy)-phenoxy eckige klammer zu -propionsaeuren und deren derivate, verfahren zu ihrer herstellung und diese enthaltende herbizide mittel
DD149013A5 (de)	1981-06-24	Herbizides und pflanzenregulierendes mittel
DE2809541A1 (de)	1978-09-14	Neue herbizid wirksame phenoxy- alpha-phenoxy-alkancarbonsaeurederivate
DE2652384A1 (de)	1977-05-26	Neue herbizid wirksame, kernsubstituierte phenoxy-phenoxy-alkancarbonsaeurederivate und deren verwendung zur bekaempfung von ungraesern
DD253754A5 (de)	1988-02-03	Herbizides und das pflanzenwachstum hemmendes mittel
EP0036390B1 (fr)	1983-10-26	Diphényléther-urées à propriétés herbicides
EP0008624B1 (fr)	1982-02-24	Esters d'acides O-(pyridyloxy-phényl)-lactiques, leur procédé de préparation et leur utilisation comme herbicides et régulateurs de croissance de plantes
CH623725A5 (en)	1981-06-30	Herbicide containing, as active substance, novel phenoxy-alpha-phenoxyalkanecarboxylic acid derivatives
EP0007089B1 (fr)	1981-09-16	Acylanilides à activité herbicide et fungicide, procédé pour leur préparation et leur utilisation
DD204607A5 (de)	1983-12-07	Herbizide und wachstumsregulierende mittel
EP0058639B1 (fr)	1985-08-14	Esters de l'acide 2-(4-(6-halogène-quinoxalinyl-2-oxy)-phénoxy)-propionique, leurs procédés de préparation et leur application comme herbicides et régulateurs de la croissance de plantes
DE2730591A1 (de)	1978-01-12	Neue herbizid wirksame, kernsubstituierte phenoxy-phenoxy-alkancarbonsaeurederivate und deren verwendung zur bekaempfung von ungraesern
CH623986A5 (en)	1981-07-15	Herbicide and its use for the selective control of grass weeds
EP0003059B1 (fr)	1981-01-07	Alcoxyalcoylamides de l'acide 4-(p-phénoxy-phénoxy)-alpha-propionique, doués d'une activité herbicide, procédé pour leur préparation et agents herbicides les contenant et leur usage
EP0003297A1 (fr)	1979-08-08	Phenoxy-alcoyl-oxazolines, leur préparation, compositions herbicides les contenant et leur application
DE3402982A1 (de)	1985-08-01	Phenoxypropionyloxyalkanphosphonsaeureester
DD141773A5 (de)	1980-05-21	Herbizides mittel
CH624927A5 (en)	1981-08-31	Process for the preparation of novel, herbicidally active phenoxyphenoxyalkanecarboxylic acid derivatives which are substituted in the nucleus, compositions containing them, and their use for controlling weeds
EP0058885B1 (fr)	1984-03-07	4-Amino-6-(2-chloro-1-méthyl-cyclopropyl)-3-méthylthio-1,2,4-triazine-5-one à activité herbicide
EP0071096B1 (fr)	1984-11-07	N-aminométhylhalogènacétanilides, procédé de leur préparation et leur utilisation dans le contrôle de croissance indésirable des herbes
DE2162046A1 (de)	1972-08-10	Verfahren zur Herstellung neuer herbizider Wirkstoffe
DD202088A5 (de)	1983-08-31	Herbizides mittel
EP0003586A1 (fr)	1979-08-22	Dérivés d'acides phénoxy-acétiques, procédé pour leur préparation et leur utilisation comme herbicides