CS201016B2 - Herbicide - Google Patents

Herbicide Download PDF

Info

Publication number: CS201016B2
Authority: CS; Czechoslovakia
Prior art keywords: group; formula; compound; mixture; preparation
Prior art date: 1977-08-12

Application number

CS527278A

Other languages

Czech (cs)

English (en)

Inventor

David Cartwright

Original Assignee

Ici Ltd

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.)

1977-08-12

Filing date

1978-08-11

Publication date

1980-10-31

1978-08-11 Application filed by Ici Ltd filed Critical Ici Ltd

1980-10-31 Publication of CS201016B2 publication Critical patent/CS201016B2/cs

Links

230000002363 herbicidal effect Effects 0.000 title claims description 11
239000004009 herbicide Substances 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 122
239000000203 mixture Substances 0.000 claims description 89
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 61
239000000460 chlorine Substances 0.000 claims description 52
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
-1 phenyloxycarbonyl Chemical group 0.000 claims description 24
229910052801 chlorine Inorganic materials 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 16
239000004480 active ingredient Substances 0.000 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 12
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 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 9
229910052799 carbon Inorganic materials 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 8
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 7
229910052794 bromium Inorganic materials 0.000 claims description 6
229910052751 metal Inorganic materials 0.000 claims description 6
239000002184 metal Substances 0.000 claims description 6
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 5
229910052740 iodine Inorganic materials 0.000 claims description 5
150000003222 pyridines Chemical class 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
239000013543 active substance Substances 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
239000011630 iodine Substances 0.000 claims description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
IOYNQIMAUDJVEI-BMVIKAAMSA-N Tepraloxydim Chemical group C1C(=O)C(C(=N/OC\C=C\Cl)/CC)=C(O)CC1C1CCOCC1 IOYNQIMAUDJVEI-BMVIKAAMSA-N 0.000 claims 1
208000037386 Typhoid Diseases 0.000 claims 1
125000001183 hydrocarbyl group Chemical group 0.000 claims 1
235000019260 propionic acid Nutrition 0.000 claims 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
FUSNMLFNXJSCDI-UHFFFAOYSA-N tolnaftate Chemical group C=1C=C2C=CC=CC2=CC=1OC(=S)N(C)C1=CC=CC(C)=C1 FUSNMLFNXJSCDI-UHFFFAOYSA-N 0.000 claims 1
201000008297 typhoid fever Diseases 0.000 claims 1
235000013522 vodka Nutrition 0.000 claims 1
238000002360 preparation method Methods 0.000 description 79
239000003921 oil Substances 0.000 description 64
239000000243 solution Substances 0.000 description 60
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 59
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 56
239000000047 product Substances 0.000 description 45
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 43
238000000034 method Methods 0.000 description 42
238000006243 chemical reaction Methods 0.000 description 35
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
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238000009835 boiling Methods 0.000 description 26
238000012360 testing method Methods 0.000 description 26
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
241000196324 Embryophyta Species 0.000 description 23
239000000284 extract Substances 0.000 description 21
238000010992 reflux Methods 0.000 description 21
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 21
239000002904 solvent Substances 0.000 description 20
238000003756 stirring Methods 0.000 description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
239000007787 solid Substances 0.000 description 16
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239000002253 acid Substances 0.000 description 15
239000000706 filtrate Substances 0.000 description 15
239000010410 layer Substances 0.000 description 15
239000003208 petroleum Substances 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 14
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
229910000027 potassium carbonate Inorganic materials 0.000 description 12
230000002829 reductive effect Effects 0.000 description 11
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 11
244000075850 Avena orientalis Species 0.000 description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
235000007319 Avena orientalis Nutrition 0.000 description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
239000002585 base Substances 0.000 description 8
230000006378 damage Effects 0.000 description 8
239000012259 ether extract Substances 0.000 description 8
239000007788 liquid Substances 0.000 description 8
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 8
238000004809 thin layer chromatography Methods 0.000 description 8
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 7
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 7
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
239000000839 emulsion Substances 0.000 description 7
229910052708 sodium Inorganic materials 0.000 description 7
239000011734 sodium Substances 0.000 description 7
239000004094 surface-active agent Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
238000005481 NMR spectroscopy Methods 0.000 description 6
229950005499 carbon tetrachloride Drugs 0.000 description 6
150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
239000003085 diluting agent Substances 0.000 description 6
238000001704 evaporation Methods 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
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KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 5
244000038559 crop plants Species 0.000 description 5
239000006185 dispersion Substances 0.000 description 5
238000004821 distillation Methods 0.000 description 5
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229910000040 hydrogen fluoride Inorganic materials 0.000 description 5
239000000463 material Substances 0.000 description 5
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230000008018 melting Effects 0.000 description 5
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239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
229960001866 silicon dioxide Drugs 0.000 description 5
229910000029 sodium carbonate Inorganic materials 0.000 description 5
239000002689 soil Substances 0.000 description 5
GDFCUTHAIBYLSX-UHFFFAOYSA-N 2,5-dichloro-3-(difluoromethyl)pyridine Chemical compound FC(F)C1=CC(Cl)=CN=C1Cl GDFCUTHAIBYLSX-UHFFFAOYSA-N 0.000 description 4
CZVBTOGZRGRJSC-UHFFFAOYSA-N 2,5-dichloro-3-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC(Cl)=CN=C1Cl CZVBTOGZRGRJSC-UHFFFAOYSA-N 0.000 description 4
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SFZCNBIFKDRMGX-UHFFFAOYSA-N sulfur hexafluoride Chemical compound FS(F)(F)(F)(F)F SFZCNBIFKDRMGX-UHFFFAOYSA-N 0.000 description 4
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ODNBVEIAQAZNNM-UHFFFAOYSA-N 1-(6-chloroimidazo[1,2-b]pyridazin-3-yl)ethanone Chemical compound C1=CC(Cl)=NN2C(C(=O)C)=CN=C21 ODNBVEIAQAZNNM-UHFFFAOYSA-N 0.000 description 3
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239000003350 kerosene Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
239000012669 liquid formulation Substances 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
150000004668 long chain fatty acids Chemical class 0.000 description 1
230000007774 longterm Effects 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
235000009973 maize Nutrition 0.000 description 1
238000005259 measurement Methods 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
229940050176 methyl chloride Drugs 0.000 description 1
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
229940055577 oleyl alcohol Drugs 0.000 description 1
XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
WROZTZHKRRNHBS-UHFFFAOYSA-N phenyl propaneperoxoate Chemical compound CCC(=O)OOC1=CC=CC=C1 WROZTZHKRRNHBS-UHFFFAOYSA-N 0.000 description 1
HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
229940067157 phenylhydrazine Drugs 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
230000008654 plant damage Effects 0.000 description 1
239000004033 plastic Substances 0.000 description 1
239000004304 potassium nitrite Substances 0.000 description 1
235000010289 potassium nitrite Nutrition 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
RMIGTEGRHJUHHM-UHFFFAOYSA-N propan-1-ol;hydrochloride Chemical compound Cl.CCCO RMIGTEGRHJUHHM-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
235000012045 salad Nutrition 0.000 description 1
230000009528 severe injury Effects 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
239000000344 soap Substances 0.000 description 1
239000004289 sodium hydrogen sulphite Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
HFQQZARZPUDIFP-UHFFFAOYSA-M sodium;2-dodecylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O HFQQZARZPUDIFP-UHFFFAOYSA-M 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000002594 sorbent Substances 0.000 description 1
229940035044 sorbitan monolaurate Drugs 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000005507 spraying Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
238000001256 steam distillation Methods 0.000 description 1
QHMQWEPBXSHHLH-UHFFFAOYSA-N sulfur tetrafluoride Chemical compound FS(F)(F)F QHMQWEPBXSHHLH-UHFFFAOYSA-N 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
210000001685 thyroid gland Anatomy 0.000 description 1
238000001665 trituration Methods 0.000 description 1
238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
238000012795 verification Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Landscapes

Pyridine Compounds (AREA)

CS527278A 1977-08-12 1978-08-11 Herbicide CS201016B2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB3403977		1977-08-12
GB4454177		1977-10-26

Publications (1)

Publication Number	Publication Date
CS201016B2 true CS201016B2 (en)	1980-10-31

Family

ID=26262130

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS527278A CS201016B2 (en)	1977-08-12	1978-08-11	Herbicide

Country Status (3)

Country	Link
CS (1)	CS201016B2 (pl)
HU (1)	HU185767B (pl)
PL (1)	PL208964A1 (pl)

1978
- 1978-08-09 HU HUIE000843 patent/HU185767B/hu unknown
- 1978-08-10 PL PL20896478A patent/PL208964A1/pl unknown
- 1978-08-11 CS CS527278A patent/CS201016B2/cs unknown

Also Published As

Publication number	Publication date
HU185767B (en)	1985-03-28
PL208964A1 (pl)	1979-09-24

Publication	Publication Date	Title
US4925947A (en)	1990-05-15	Precursors to herbicidal pyridine compounds
US5250690A (en)	1993-10-05	Haloalkoxy anilide derivatives of 2-4(-heterocyclic oxyphenoxy)alkanoic or alkenoic acids and their use as herbicides
JP3157234B2 (ja)	2001-04-16	除草性カルボキシアミド誘導体
JPH092906A (ja)	1997-01-07	プロペン酸誘導体、その製造法及びそれを含有する殺菌組成物
JPS6250466B2 (pl)	1987-10-24
WO1994022833A1 (en)	1994-10-13	Herbicidal heterocyclic-substituted pyridines
DK164595B (da)	1992-07-20	3-methoxy-2-pyridyl-methylacrylater, fremgangsmaade til fremstilling deraf, middel indeholdende forbindelserne og disses eller midlets anvendelse til bekaempelse af svampe
IE44934B1 (en)	1982-05-19	2-(phenoxyphenoxy)-propionic acid derivatives and their herbicidal compositions
US4565568A (en)	1986-01-21	Pyridyl(oxy/thio)phenoxy compounds, herbicidal compositions and methods
CA1244441A (en)	1988-11-08	2(4-pyridyl-2-oxyphenoxy) propanol compounds
RU2070883C1 (ru)	1996-12-27	Производные пиколинамида, способы их получения, промежуточные соединения для получения производных пиколинамида, способ их получения, способы борьбы с нежелательной растительностью
EP0050019B1 (en)	1986-04-09	3-keto-4-(4'-aromatically substituted-phenoxy) compounds, their 3- alkylated enol and 2,3-hydrogenated derivatives and the use thereof for the control of weeds
CS203034B2 (en)	1981-02-27	Herbicide and process for preparing effective compounds
CS201016B2 (en)	1980-10-31	Herbicide
EP0205821A1 (en)	1986-12-30	Haloalkoxy anilide derivatives of 2-(4-heterocyclic oxyphenoxy)-alkanoic acids and their use as herbicides
JPH0245459A (ja)	1990-02-15	除草活性を有するアクリロニトリル誘導体
CS236791B2 (en)	1985-05-15	Herbicide agent and processing method of active component
IE47552B1 (en)	1984-04-18	-(4-(5-fluoromethyl-2-pyridyloxy)-phenoxy)alkane-carboxylic acid derivatives and their use as herbicides
US4460400A (en)	1984-07-17	Dihydropyrones, novel starting products used therein, compositions containing the novel dihydropyrones as active ingredients, and the use thereof for combating weeds
SI7811927A8 (sl)	1994-12-31	Postopek za pripravo piridinskih spojin
JPH0433788B2 (pl)	1992-06-04
JPH06145007A (ja)	1994-05-24	除草剤組成物
JPH05148213A (ja)	1993-06-15	シアノケトン誘導体
NZ201042A (en)	1985-01-31	Substituted phenoxypropionates and herbicidal compositions