CH621921A5 - - Google Patents

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Info

Publication number: CH621921A5
Authority: CH; Switzerland
Prior art keywords: carbon atoms; alkyl; halogen; benzyl; formula
Prior art date: 1972-05-17

Application number

CH681473A

Other languages

German (de)

English (en)

Inventor

Werner Becker

Peter Dr Langelueddeke

Heinrich Dr Leditschke

Helmut Dr Nahm

Friedhelm Dr Schwerdtle

Original Assignee

Hoechst 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.)

1972-05-17

Filing date

1973-05-14

Publication date

1981-03-13

1973-05-14 Application filed by Hoechst Ag filed Critical Hoechst Ag

1981-03-13 Publication of CH621921A5 publication Critical patent/CH621921A5/de

Links

150000001875 compounds Chemical class 0.000 claims description 54
125000004432 carbon atom Chemical group C* 0.000 claims description 37
230000000694 effects Effects 0.000 claims description 28
241000196324 Embryophyta Species 0.000 claims description 26
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
-1 substituted Chemical class 0.000 claims description 21
239000000203 mixture Substances 0.000 claims description 20
125000000217 alkyl group Chemical group 0.000 claims description 18
238000002360 preparation method Methods 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 16
229910052736 halogen Inorganic materials 0.000 claims description 16
150000002367 halogens Chemical group 0.000 claims description 16
238000000034 method Methods 0.000 claims description 13
244000038559 crop plants Species 0.000 claims description 9
230000002363 herbicidal effect Effects 0.000 claims description 8
238000009472 formulation Methods 0.000 claims description 7
150000007513 acids Chemical class 0.000 claims description 6
239000004009 herbicide Substances 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
150000007529 inorganic bases Chemical class 0.000 claims description 4
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
239000000654 additive Substances 0.000 claims description 3
150000001768 cations Chemical class 0.000 claims description 3
150000007530 organic bases Chemical class 0.000 claims description 3
BNJMRELGMDUDDB-UHFFFAOYSA-N $l^{1}-sulfanylbenzene Chemical compound [S]C1=CC=CC=C1 BNJMRELGMDUDDB-UHFFFAOYSA-N 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
150000003973 alkyl amines Chemical class 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
230000008635 plant growth Effects 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims 2
229960002944 cyclofenil Drugs 0.000 claims 1
150000002632 lipids Chemical class 0.000 claims 1
230000004060 metabolic process Effects 0.000 claims 1
238000011282 treatment Methods 0.000 description 40
241000209504 Poaceae Species 0.000 description 32
239000004480 active ingredient Substances 0.000 description 25
241000743985 Alopecurus Species 0.000 description 18
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 18
235000021536 Sugar beet Nutrition 0.000 description 17
239000003795 chemical substances by application Substances 0.000 description 17
241000192043 Echinochloa Species 0.000 description 15
240000001592 Amaranthus caudatus Species 0.000 description 14
235000009328 Amaranthus caudatus Nutrition 0.000 description 14
125000001309 chloro group Chemical group Cl* 0.000 description 14
239000000126 substance Substances 0.000 description 14
235000010469 Glycine max Nutrition 0.000 description 13
244000068988 Glycine max Species 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
240000004713 Pisum sativum Species 0.000 description 12
XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 12
244000025254 Cannabis sativa Species 0.000 description 11
235000010582 Pisum sativum Nutrition 0.000 description 11
230000000052 comparative effect Effects 0.000 description 11
241000209761 Avena Species 0.000 description 10
MZHCENGPTKEIGP-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1Cl MZHCENGPTKEIGP-UHFFFAOYSA-N 0.000 description 9
230000006378 damage Effects 0.000 description 9
239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 8
244000299507 Gossypium hirsutum Species 0.000 description 8
241001300479 Macroptilium Species 0.000 description 8
WYKYKTKDBLFHCY-UHFFFAOYSA-N chloridazon Chemical compound O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1 WYKYKTKDBLFHCY-UHFFFAOYSA-N 0.000 description 8
239000011734 sodium Substances 0.000 description 8
235000007319 Avena orientalis Nutrition 0.000 description 7
229920000742 Cotton Polymers 0.000 description 7
LKJPSUCKSLORMF-UHFFFAOYSA-N Monolinuron Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C=C1 LKJPSUCKSLORMF-UHFFFAOYSA-N 0.000 description 7
239000005594 Phenmedipham Substances 0.000 description 7
241000209140 Triticum Species 0.000 description 7
235000021307 Triticum Nutrition 0.000 description 7
IDOWTHOLJBTAFI-UHFFFAOYSA-N phenmedipham Chemical compound COC(=O)NC1=CC=CC(OC(=O)NC=2C=C(C)C=CC=2)=C1 IDOWTHOLJBTAFI-UHFFFAOYSA-N 0.000 description 7
239000000080 wetting agent Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
239000005493 Chloridazon (aka pyrazone) Substances 0.000 description 6
235000017896 Digitaria Nutrition 0.000 description 6
241001303487 Digitaria <clam> Species 0.000 description 6
240000005979 Hordeum vulgare Species 0.000 description 6
235000007340 Hordeum vulgare Nutrition 0.000 description 6
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 6
239000005573 Linuron Substances 0.000 description 6
SAQSTQBVENFSKT-UHFFFAOYSA-M TCA-sodium Chemical compound [Na+].[O-]C(=O)C(Cl)(Cl)Cl SAQSTQBVENFSKT-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
241001148683 Zostera marina Species 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
239000007921 spray Substances 0.000 description 6
240000002791 Brassica napus Species 0.000 description 5
235000004977 Brassica sinapistrum Nutrition 0.000 description 5
244000020551 Helianthus annuus Species 0.000 description 5
235000003222 Helianthus annuus Nutrition 0.000 description 5
241000209082 Lolium Species 0.000 description 5
240000007594 Oryza sativa Species 0.000 description 5
239000004495 emulsifiable concentrate Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
235000007164 Oryza sativa Nutrition 0.000 description 4
240000008042 Zea mays Species 0.000 description 4
235000002017 Zea mays subsp mays Nutrition 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
239000008187 granular material Substances 0.000 description 4
230000012010 growth Effects 0.000 description 4
235000009566 rice Nutrition 0.000 description 4
239000002689 soil Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
235000017060 Arachis glabrata Nutrition 0.000 description 3
244000105624 Arachis hypogaea Species 0.000 description 3
235000010777 Arachis hypogaea Nutrition 0.000 description 3
235000018262 Arachis monticola Nutrition 0.000 description 3
235000005781 Avena Nutrition 0.000 description 3
240000008067 Cucumis sativus Species 0.000 description 3
235000010799 Cucumis sativus var sativus Nutrition 0.000 description 3
235000002767 Daucus carota Nutrition 0.000 description 3
244000000626 Daucus carota Species 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 3
150000001735 carboxylic acids Chemical class 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
241001233957 eudicotyledons Species 0.000 description 3
239000003337 fertilizer Substances 0.000 description 3
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 3
235000009973 maize Nutrition 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
DGPBHERUGBOSFZ-UHFFFAOYSA-N n-but-3-yn-2-yl-2-chloro-n-phenylacetamide Chemical compound C#CC(C)N(C(=O)CCl)C1=CC=CC=C1 DGPBHERUGBOSFZ-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
235000020232 peanut Nutrition 0.000 description 3
238000009331 sowing Methods 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
239000005995 Aluminium silicate Substances 0.000 description 2
241000219318 Amaranthus Species 0.000 description 2
241001666377 Apera Species 0.000 description 2
240000007087 Apium graveolens Species 0.000 description 2
235000015849 Apium graveolens Dulce Group Nutrition 0.000 description 2
235000010591 Appio Nutrition 0.000 description 2
241000209764 Avena fatua Species 0.000 description 2
241000219112 Cucumis Species 0.000 description 2
235000015510 Cucumis melo subsp melo Nutrition 0.000 description 2
244000058871 Echinochloa crus-galli Species 0.000 description 2
241001101998 Galium Species 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
235000021506 Ipomoea Nutrition 0.000 description 2
241000207783 Ipomoea Species 0.000 description 2
240000004658 Medicago sativa Species 0.000 description 2
235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
235000002637 Nicotiana tabacum Nutrition 0.000 description 2
244000061176 Nicotiana tabacum Species 0.000 description 2
235000011999 Panicum crusgalli Nutrition 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
241000220261 Sinapis Species 0.000 description 2
241000219793 Trifolium Species 0.000 description 2
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 2
239000013543 active substance Substances 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
210000003608 fece Anatomy 0.000 description 2
239000000463 material Substances 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
238000005406 washing Methods 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 description 1
YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 description 1
OVSKIKFHRZPJSS-DOMIDYPGSA-N 2-(2,4-dichlorophenoxy)acetic acid Chemical compound OC(=O)[14CH2]OC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-DOMIDYPGSA-N 0.000 description 1
OWZPCEFYPSAJFR-UHFFFAOYSA-N 2-(butan-2-yl)-4,6-dinitrophenol Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O OWZPCEFYPSAJFR-UHFFFAOYSA-N 0.000 description 1
IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
TVSPPYGAFOVROT-UHFFFAOYSA-N 2-phenoxybutanoic acid Chemical compound CCC(C(O)=O)OC1=CC=CC=C1 TVSPPYGAFOVROT-UHFFFAOYSA-N 0.000 description 1
XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 1
ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical compound CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
XQMRZWSYBUCVAX-UHFFFAOYSA-N 4-(4-chlorophenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(Cl)C=C1 XQMRZWSYBUCVAX-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
CTSLUCNDVMMDHG-UHFFFAOYSA-N 5-bromo-3-(butan-2-yl)-6-methylpyrimidine-2,4(1H,3H)-dione Chemical compound CCC(C)N1C(=O)NC(C)=C(Br)C1=O CTSLUCNDVMMDHG-UHFFFAOYSA-N 0.000 description 1
MDBGGTQNNUOQRC-UHFFFAOYSA-N Allidochlor Chemical compound ClCC(=O)N(CC=C)CC=C MDBGGTQNNUOQRC-UHFFFAOYSA-N 0.000 description 1
244000291564 Allium cepa Species 0.000 description 1
241001621841 Alopecurus myosuroides Species 0.000 description 1
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235000007320 Avena fatua Nutrition 0.000 description 1
235000000832 Ayote Nutrition 0.000 description 1
RRNIZKPFKNDSRS-UHFFFAOYSA-N Bensulide Chemical compound CC(C)OP(=S)(OC(C)C)SCCNS(=O)(=O)C1=CC=CC=C1 RRNIZKPFKNDSRS-UHFFFAOYSA-N 0.000 description 1
ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
239000004604 Blowing Agent Substances 0.000 description 1
240000007124 Brassica oleracea Species 0.000 description 1
235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
WLYGSPLCNKYESI-RSUQVHIMSA-N Carthamin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1[C@@]1(O)C(O)=C(C(=O)\C=C\C=2C=CC(O)=CC=2)C(=O)C(\C=C\2C([C@](O)([C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)C(O)=C(C(=O)\C=C\C=3C=CC(O)=CC=3)C/2=O)=O)=C1O WLYGSPLCNKYESI-RSUQVHIMSA-N 0.000 description 1
241000208809 Carthamus Species 0.000 description 1
VCBRBUKGTWLJOB-UHFFFAOYSA-N Chloranocryl Chemical compound CC(=C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 VCBRBUKGTWLJOB-UHFFFAOYSA-N 0.000 description 1
YJKIALIXRCSISK-UHFFFAOYSA-N Chlorfenprop-methyl Chemical group COC(=O)C(Cl)CC1=CC=C(Cl)C=C1 YJKIALIXRCSISK-UHFFFAOYSA-N 0.000 description 1
244000241235 Citrullus lanatus Species 0.000 description 1
235000012828 Citrullus lanatus var citroides Nutrition 0.000 description 1
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HCRWJJJUKUVORR-UHFFFAOYSA-N Desmetryn Chemical compound CNC1=NC(NC(C)C)=NC(SC)=N1 HCRWJJJUKUVORR-UHFFFAOYSA-N 0.000 description 1
244000152970 Digitaria sanguinalis Species 0.000 description 1
235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
RDJTWDKSYLLHRW-UHFFFAOYSA-N Dinoseb acetate Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(C)=O RDJTWDKSYLLHRW-UHFFFAOYSA-N 0.000 description 1
QAHFOPIILNICLA-UHFFFAOYSA-N Diphenamid Chemical compound C=1C=CC=CC=1C(C(=O)N(C)C)C1=CC=CC=C1 QAHFOPIILNICLA-UHFFFAOYSA-N 0.000 description 1
239000005630 Diquat Substances 0.000 description 1
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239000005510 Diuron Substances 0.000 description 1
240000002092 Echinochloa colona Species 0.000 description 1
235000014716 Eleusine indica Nutrition 0.000 description 1
244000025670 Eleusine indica Species 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
239000005533 Fluometuron Substances 0.000 description 1
HHMCAJWVGYGUEF-UHFFFAOYSA-N Fluorodifen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O HHMCAJWVGYGUEF-UHFFFAOYSA-N 0.000 description 1
GXAMYUGOODKVRM-UHFFFAOYSA-N Flurecol Chemical compound C1=CC=C2C(C(=O)O)(O)C3=CC=CC=C3C2=C1 GXAMYUGOODKVRM-UHFFFAOYSA-N 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
235000003228 Lactuca sativa Nutrition 0.000 description 1
240000008415 Lactuca sativa Species 0.000 description 1
239000005572 Lenacil Substances 0.000 description 1
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240000006240 Linum usitatissimum Species 0.000 description 1
235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
DDUIUBPJPOKOMV-UHFFFAOYSA-N Methoprotryne Chemical compound COCCCNC1=NC(NC(C)C)=NC(SC)=N1 DDUIUBPJPOKOMV-UHFFFAOYSA-N 0.000 description 1
KXGYBSNVFXBPNO-UHFFFAOYSA-N Monalide Chemical compound CCCC(C)(C)C(=O)NC1=CC=C(Cl)C=C1 KXGYBSNVFXBPNO-UHFFFAOYSA-N 0.000 description 1
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239000007832 Na2SO4 Substances 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
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235000015622 Pisum sativum var macrocarpon Nutrition 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
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PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
229920002125 Sokalan® Polymers 0.000 description 1
240000003768 Solanum lycopersicum Species 0.000 description 1
MWBPRDONLNQCFV-UHFFFAOYSA-N Tri-allate Chemical compound CC(C)N(C(C)C)C(=O)SCC(Cl)=C(Cl)Cl MWBPRDONLNQCFV-UHFFFAOYSA-N 0.000 description 1
ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical class O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 1
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240000006677 Vicia faba Species 0.000 description 1
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235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
AKGGOMZLAADIQD-UHFFFAOYSA-N [3-(methoxycarbonylamino)phenyl]-(3-methylphenyl)carbamic acid Chemical group COC(=O)NC1=CC=CC(N(C(O)=O)C=2C=C(C)C=CC=2)=C1 AKGGOMZLAADIQD-UHFFFAOYSA-N 0.000 description 1
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229940051881 anilide analgesics and antipyretics Drugs 0.000 description 1
150000003931 anilides Chemical class 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
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MCOQHIWZJUDQIC-UHFFFAOYSA-N barban Chemical compound ClCC#CCOC(=O)NC1=CC=CC(Cl)=C1 MCOQHIWZJUDQIC-UHFFFAOYSA-N 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
239000008280 blood Substances 0.000 description 1
229960003369 butacaine Drugs 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
IVUXTESCPZUGJC-UHFFFAOYSA-N chloroxuron Chemical compound C1=CC(NC(=O)N(C)C)=CC=C1OC1=CC=C(Cl)C=C1 IVUXTESCPZUGJC-UHFFFAOYSA-N 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
SYJFEGQWDCRVNX-UHFFFAOYSA-N diquat Chemical compound C1=CC=[N+]2CC[N+]3=CC=CC=C3C2=C1 SYJFEGQWDCRVNX-UHFFFAOYSA-N 0.000 description 1
238000010410 dusting Methods 0.000 description 1
235000005489 dwarf bean Nutrition 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
RZILCCPWPBTYDO-UHFFFAOYSA-N fluometuron Chemical compound CN(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 RZILCCPWPBTYDO-UHFFFAOYSA-N 0.000 description 1
238000005469 granulation Methods 0.000 description 1
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238000000227 grinding Methods 0.000 description 1
244000080020 horsebean Species 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
NRXQIUSYPAHGNM-UHFFFAOYSA-N ioxynil Chemical compound OC1=C(I)C=C(C#N)C=C1I NRXQIUSYPAHGNM-UHFFFAOYSA-N 0.000 description 1
229910052622 kaolinite Inorganic materials 0.000 description 1
235000021374 legumes Nutrition 0.000 description 1
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229920005610 lignin Polymers 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
JITOKQVGRJSHHA-UHFFFAOYSA-M monosodium methyl arsenate Chemical compound [Na+].C[As](O)([O-])=O JITOKQVGRJSHHA-UHFFFAOYSA-M 0.000 description 1
229940084719 monosodium methylarsonate Drugs 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
125000001117 oleyl group Polymers [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
230000001151 other effect Effects 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 1
239000004584 polyacrylic acid Substances 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 description 1
NLZGRCKPBHBOGE-UHFFFAOYSA-N prop-2-enyl n,n-diethylcarbamodithioate Chemical compound CCN(CC)C(=S)SCC=C NLZGRCKPBHBOGE-UHFFFAOYSA-N 0.000 description 1
MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 1
235000015136 pumpkin Nutrition 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000010453 quartz Substances 0.000 description 1
239000004576 sand Substances 0.000 description 1
ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
241000894007 species Species 0.000 description 1
238000005507 spraying Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- 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
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH681473A 1972-05-17 1973-05-14 CH621921A5 (nl)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2223894A DE2223894C3 (de)	1972-05-17	1972-05-17	Herbizide Mittel auf Basis von Phenoxycarbonsäurederivaten

Publications (1)

Publication Number	Publication Date
CH621921A5 true CH621921A5 (nl)	1981-03-13

Family

ID=5845046

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH681473A CH621921A5 (nl)	1972-05-17	1973-05-14

Country Status (32)

Country	Link
US (1)	US3954442A (nl)
JP (1)	JPS548727B2 (nl)
AR (1)	AR214697A1 (nl)
AT (1)	AT332676B (nl)
AU (1)	AU474130B2 (nl)
BE (1)	BE799554A (nl)
BG (1)	BG28017A3 (nl)
BR (1)	BR7303586D0 (nl)
CA (1)	CA1033584A (nl)
CH (1)	CH621921A5 (nl)
CS (1)	CS170471B2 (nl)
CU (1)	CU33903A (nl)
DD (1)	DD105714A5 (nl)
DE (1)	DE2223894C3 (nl)
EG (1)	EG11004A (nl)
FR (1)	FR2184906B1 (nl)
GB (1)	GB1423006A (nl)
HU (1)	HU170009B (nl)
IE (1)	IE37638B1 (nl)
IL (1)	IL42278A (nl)
IT (1)	IT987464B (nl)
KE (1)	KE2764A (nl)
MY (1)	MY7700316A (nl)
NL (1)	NL173469C (nl)
OA (1)	OA04408A (nl)
PH (1)	PH10381A (nl)
PL (1)	PL89252B1 (nl)
SE (1)	SE400879B (nl)
SU (1)	SU610470A3 (nl)
TR (1)	TR20186A (nl)
ZA (1)	ZA732653B (nl)
ZM (1)	ZM8473A1 (nl)

Families Citing this family (115)

* Cited by examiner, † Cited by third party
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US4058552A (en) *	1969-01-31	1977-11-15	Orchimed Sa	Esters of p-carbonylphenoxy-isobutyric acids
BE786644A (fr) *	1971-07-23	1973-01-24	Hoechst Ag	Derives d'acides phenoxy-4 phenoxy-alcane-carboxyliques leur preparation et les medicaments qui en contiennent
US4093446A (en) *	1972-03-14	1978-06-06	Rohm And Haas Company	Herbicidal 4-trifluoromethyl-4-nitrodiphenyl ethers
US4067892A (en) *	1973-08-23	1978-01-10	Beecham Group Limited	Substituted (4-carboxyphenoxy) phenyl alkane compounds
IL45894A0 (en) *	1973-10-25	1974-12-31	Ciba Geigy Ag	New aryl alkyl ethers,their preparation and their use in pest control
DE2427270A1 (de) *	1974-06-06	1975-12-18	Hoechst Ag	Herbizide mittel
CS185694B2 (en) *	1974-07-17	1978-10-31	Ishihara Sangyo Kaisha	Herbicidal agent
US4156011A (en) *	1974-09-30	1979-05-22	Societe Anonyme Dite: Laboratoire L. Lafon	Sulphur- and oxygen-containing diaryl compounds
CH609024A5 (en) *	1974-09-30	1979-02-15	Lafon Labor	Process for the preparation of new sulphur-containing diaryl and oxygen-containing diaryl compounds
GB1519147A (en) *	1974-09-30	1978-07-26	Lafon Labor	Sulphur and oxygen-containing diaryl compounds
DK154074C (da) *	1974-10-17	1989-02-27	Ishihara Sangyo Kaisha	Alfa-(4-(5 eller 3,5 substitueret pyridyl-2-oxy)-phenoxy)-alkan-carboxylsyrer eller derivater deraf til anvendelse som herbicider, herbicidt middel samt fremgangsmaader til bekaempelse af ukrudt
US4092151A (en) *	1974-10-17	1978-05-30	Ishihara Sangyo Kaisha, Ltd.	Herbicidal compound, herbicidal composition containing the same and method of use thereof
US4083714A (en) *	1974-10-17	1978-04-11	Ishihara Sangyo Kaisha, Ltd.	Alkoxyalkyl esters of substituted pyridyloxyphenoxy-2-propanoic acids, herbicidal composition containing the same and method of use thereof
US4107329A (en) *	1974-12-06	1978-08-15	Imperial Chemical Industries Limited	Fluorinated compounds as therapeutics
GB1499508A (en) *	1974-12-06	1978-02-01	Ici Ltd	3,3,3-trifluoropropionic acid derivatives
JPS5941967B2 (ja) *	1974-12-23	1984-10-11	三井東圧化学株式会社	殺草剤
JPS51136823A (en) *	1975-05-16	1976-11-26	Mitsui Toatsu Chem Inc	Weedkiller
US4151302A (en) *	1975-06-28	1979-04-24	Merck Patent Gesellschaft Mit Beschrankter Haftung	Araliphatic dihalogen compounds composition and method of use
DE2537290A1 (de) *	1975-08-21	1977-03-03	Bayer Ag	Mittel zur selektiven unkrautbekaempfung in rueben
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
US4203758A (en) *	1975-09-27	1980-05-20	Ishihara Sangyo Kaisha Limited	Herbicidal phenoxy-phenoxyalkane thio esters
US4193790A (en) *	1975-11-20	1980-03-18	Ishihara Sangyo Kabushiki Kaisha Ltd.	Novel herbicidally active, nuclear-substituted phenoxy-phenoxy-alkanecarboxylic acid derivatives and use thereof for controlling grass-like weeds
US4183743A (en) *	1975-11-20	1980-01-15	Ishihara Sangyo Kaisha Ltd.	Novel herbicidally active, nuclear-substituted phenoxy-phenoxy-alkanecarboxylic acid derivatives and use thereof for controlling grass-like weeds
US4205978A (en) *	1975-11-20	1980-06-03	Ishihara Sangyo Kaisha, Ltd.	Novel herbicidally active, nuclear-substituted phenoxy-phenoxyalkanecarboxylic acid derivatives and use thereof for controlling grass-like weeds
US4106925A (en) *	1975-11-20	1978-08-15	Ishihara Sangyo Kaisha Ltd.	Novel herbicidally active, nuclear-substituted phenoxy-phenoxy-alkanecarboxylic acid derivatives and use thereof for controlling grass-like weeds
DE2601548C2 (de) *	1976-01-16	1984-01-26	Hoechst Ag, 6230 Frankfurt	2-[4-(2'-Chlor-4'-bromphenoxy)-phenoxy]-propionsäure und Derivate sowie diese enthaltende herbizide Mittel
ES457540A1 (es) *	1976-04-13	1978-10-01	Ishihara Sangyo Kaisha	Procedimiento para la preparacion de acido alfa-(4-(2-nitro-4-halogenfenoxi) fenoxil) propionico, sus sales y esteres alquilicos.
JPS52131540A (en) *	1976-04-14	1977-11-04	Ishihara Sangyo Kaisha Ltd	Phenoxyvaleric acid derivatives and herbicides therefrom
DE2617804C2 (de) *	1976-04-23	1985-01-24	Hoechst Ag, 6230 Frankfurt	2-(4-Phenoxy phenoxy)-propionsäurederivate und ihre Verwendung als Herbizide
DE2623558C2 (de) *	1976-05-26	1984-12-06	Hoechst Ag, 6230 Frankfurt	2-[4'-Phenoxy-phenoxy]propionsäure-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende herbizide Mittel
DE2628384C2 (de) *	1976-06-24	1984-09-27	Hoechst Ag, 6230 Frankfurt	2-(4-Phenoxyphenoxy)- bzw. 2-(4-Benzylphenoxy)-propionsäurederivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Pflanzenbehandlungsmittel
DE2632581C2 (de) *	1976-07-20	1982-07-15	Hoechst Ag, 6000 Frankfurt	Substituierte Nitrodiphenylether, Verfahren zu ihrer Herstellung und diese enthaltende herbizide Mittel
US4133675A (en) *	1976-07-23	1979-01-09	Ciba-Geigy Corporation	Pyridyloxy-phenoxy-alkanecarboxylic acid derivatives which are effective as herbicides and as agents regulating plant growth
CH624087A5 (en) *	1976-08-25	1981-07-15	Hoechst Ag	Process for the preparation of phenoxyphenoxypropionic acid derivatives
US4108628A (en) *	1976-08-26	1978-08-22	E. I. Du Pont De Nemours And Company	Cycloalkanopyrazole herbicides mixtures
CH626318A5 (nl) *	1977-03-08	1981-11-13	Ciba Geigy Ag
US4090866A (en) *	1977-03-14	1978-05-23	O. M. Scott & Sons Company	Process for the selective control of tall fescue in turf
US4248618A (en) *	1977-05-06	1981-02-03	Ici Australia Limited	Derivatives of (pyrimidyloxy)phenoxy-alkanecarboxylic acid and herbicidal compositions thereof
DE2861187D1 (en) *	1977-07-07	1981-12-24	Ciba Geigy Ag	Phenoxy-phenylsulfinyl-and-sulfonylalkanecarboxylic acid derivatives, method for their preparation and their use as herbicides and plant growth regulators.
EP0000351A1 (de) *	1977-07-07	1979-01-24	Ciba-Geigy Ag	Phenoxy-phenylthio-alkancarbonsäurederivate, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und als Pflanzenwachstumsregulierungsmittel
TR19824A (tr) *	1977-07-21	1980-01-24	Ishihara Sangyo Kaisha	Trilorometilpiridoksifenoksipropionik as tuerevleri ve bunlari ihtiva eden herbisidler
UA6300A1 (uk) *	1977-07-21	1994-12-29	Ісіхара Сангіо Кайся Лтд	Гербіцидний склад
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1972
- 1972-05-17 DE DE2223894A patent/DE2223894C3/de not_active Expired
1973
- 1973-04-18 ZA ZA732653A patent/ZA732653B/xx unknown
- 1973-04-19 EG EG140/73A patent/EG11004A/xx active
- 1973-04-25 TR TR20186A patent/TR20186A/xx unknown
- 1973-04-27 GB GB2021073A patent/GB1423006A/en not_active Expired
- 1973-05-04 PH PH14587A patent/PH10381A/en unknown
- 1973-05-11 US US05/359,274 patent/US3954442A/en not_active Expired - Lifetime
- 1973-05-11 NL NLAANVRAGE7306625,A patent/NL173469C/nl not_active IP Right Cessation
- 1973-05-14 CU CU7333903A patent/CU33903A/es unknown
- 1973-05-14 BG BG023595A patent/BG28017A3/xx unknown
- 1973-05-14 CH CH681473A patent/CH621921A5/de not_active IP Right Cessation
- 1973-05-15 IL IL42278A patent/IL42278A/en unknown
- 1973-05-15 ZM ZM84/73*UA patent/ZM8473A1/xx unknown
- 1973-05-15 BE BE131128A patent/BE799554A/xx not_active IP Right Cessation
- 1973-05-15 AT AT422773A patent/AT332676B/de not_active IP Right Cessation
- 1973-05-15 AU AU55695/73A patent/AU474130B2/en not_active Expired
- 1973-05-15 IT IT24118/73A patent/IT987464B/it active
- 1973-05-15 DD DD170835A patent/DD105714A5/xx unknown
- 1973-05-15 AR AR248023A patent/AR214697A1/es active
- 1973-05-16 JP JP5373273A patent/JPS548727B2/ja not_active Expired
- 1973-05-16 OA OA54911A patent/OA04408A/xx unknown
- 1973-05-16 PL PL1973162579A patent/PL89252B1/pl unknown
- 1973-05-16 IE IE776/73A patent/IE37638B1/xx unknown
- 1973-05-16 CS CS3522A patent/CS170471B2/cs unknown
- 1973-05-16 HU HUHO1570A patent/HU170009B/hu unknown
- 1973-05-16 FR FR7317665A patent/FR2184906B1/fr not_active Expired
- 1973-05-16 CA CA171,539A patent/CA1033584A/en not_active Expired
- 1973-05-16 BR BR3586/73A patent/BR7303586D0/pt unknown
- 1973-05-17 SE SE7306974A patent/SE400879B/xx unknown
- 1973-05-17 SU SU731923577A patent/SU610470A3/ru active
1977
- 1977-08-27 KE KE2764A patent/KE2764A/xx unknown
- 1977-12-30 MY MY316/77A patent/MY7700316A/xx unknown

Also Published As

Publication number	Publication date
CU33903A (es)	1981-09-09
OA04408A (fr)	1980-02-29
ATA422773A (de)	1976-01-15
BE799554A (fr)	1973-11-16
AU474130B2 (en)	1976-07-15
IT987464B (it)	1975-02-20
ZM8473A1 (en)	1974-01-21
DE2223894C3 (de)	1981-07-23
AU5569573A (en)	1974-11-21
ZA732653B (en)	1974-04-24
MY7700316A (en)	1977-12-31
GB1423006A (en)	1976-01-28
SU610470A3 (ru)	1978-06-05
IL42278A (en)	1977-08-31
CS170471B2 (nl)	1976-08-27
NL173469B (nl)	1983-09-01
BR7303586D0 (pt)	1974-06-27
BG28017A3 (en)	1980-02-25
AR214697A1 (es)	1979-07-31
CA1033584A (en)	1978-06-27
FR2184906A1 (nl)	1973-12-28
PL89252B1 (nl)	1976-11-30
NL7306625A (nl)	1973-11-20
DE2223894A1 (de)	1973-12-13
TR20186A (tr)	1980-11-01
US3954442A (en)	1976-05-04
NL173469C (nl)	1984-02-01
JPS548727B2 (nl)	1979-04-18
HU170009B (nl)	1977-03-28
IE37638B1 (en)	1977-09-14
IL42278A0 (en)	1973-07-30
JPS4954525A (nl)	1974-05-27
DE2223894B2 (de)	1980-09-11
SE400879B (sv)	1978-04-17
AT332676B (de)	1976-10-11
KE2764A (en)	1977-09-09
DD105714A5 (nl)	1974-05-12
FR2184906B1 (nl)	1977-02-11
PH10381A (en)	1977-03-02
IE37638L (en)	1973-11-17
EG11004A (en)	1976-11-30

Publication	Publication Date	Title
CH621921A5 (nl)	1981-03-13
DE2433067C3 (nl)	1978-07-13
DE2617804C2 (de)	1985-01-24	2-(4-Phenoxy phenoxy)-propionsäurederivate und ihre Verwendung als Herbizide
DE69126836T2 (de)	1998-01-02	Herbizide
DE2628384C2 (de)	1984-09-27	2-(4-Phenoxyphenoxy)- bzw. 2-(4-Benzylphenoxy)-propionsäurederivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Pflanzenbehandlungsmittel
DE2101938C2 (de)	1983-05-11	3-[2-Chlor-4-(3,3-dimethylureido)-phenyl]-5-tert.-butyl-1,3,4-oxadiazolon-(2), seine Herstellung und herbicide Zusammensetzungen, die es enthalten
EP0036390B1 (de)	1983-10-26	Diphenyläther-Harnstoffe mit herbizider Wirkung
CH636600A5 (de)	1983-06-15	2-hydroxybenzamidderivate und verwendung derselben als fungizide.
EP0007089B1 (de)	1981-09-16	Acylanilide mit herbicider und fungicider Wirkung, Verfahren zu ihrer Herstellung und ihre Verwendung
DE3533440A1 (de)	1987-03-26	N-substituierte 3,4,5,6-tetrahydrophthalimide, verfahren zu ihrer herstellung sowie ihre verwendung im pflanzenschutz
DE3101889A1 (de)	1982-08-26	"neue phenoxycarbonsaeureamide, verfahren zu ihrer herstellung und ihre verwendung als herbizide"
CH631721A5 (de)	1982-08-31	Pflanzenschutzmittel.
EP0011802B1 (de)	1982-09-15	Neue Phenoxy-phenoxypropionsäureamide, Verfahren zu ihrer Herstellung, sie enthaltende herbizide Mittel und ihre Verwendung zur Bekämpfung von Schadpflanzen
CH616687A5 (nl)	1980-04-15
CH506237A (de)	1971-04-30	Gegebenenfalls substituiertes N,N'-Bis-(carbamoyloxy)-dithiooxalimidat enthaltendes Schädlingsbekämpfungsmittel
DD215002A5 (de)	1984-10-31	Pestizide zusammensetzung
DE2919825C2 (nl)	1988-09-01
DE2941658A1 (de)	1980-04-24	Praeparat mit wachstumsregulierender wirkung und anwendung dieses praeparats im acker- und gartenbau, sowie neue hexahydropyrimidine und imidazolidine
DE3035822A1 (de)	1981-04-09	Akarizide mittel
DD200204A5 (de)	1983-03-30	Fungizide mittel
DE1810581C3 (de)	1977-12-29	N-Acyl-p-dialkylamino-phenylhydrazone, Verfahren zu ihrer Herstellung und deren Verwendung zur Bekämpfung von phytopathogene Pilzen
DE2633159C2 (de)	1982-05-27	Phosphorhaltige Verbindungen, Verfahren zu ihrer Herstellung, sowie diese Verbindungen enthaltende herbizide Mittel
DE2643445A1 (de)	1977-04-07	Mikrobizide mittel
DE2206822C3 (de)	1977-08-18	Phenoxycarbonsäureamide
DE1955892A1 (de)	1970-07-02	Herbizides und insektizides Mittel

Legal Events

Date	Code	Title	Description
1993-07-30	PL	Patent ceased
2024-10-31	PL	Patent ceased