IL41766A - Diphenyl ethers and their use as herbicides - Google Patents
Diphenyl ethers and their use as herbicidesInfo
- Publication number
- IL41766A IL41766A IL41766A IL4176673A IL41766A IL 41766 A IL41766 A IL 41766A IL 41766 A IL41766 A IL 41766A IL 4176673 A IL4176673 A IL 4176673A IL 41766 A IL41766 A IL 41766A
- Authority
- IL
- Israel
- Prior art keywords
- trifluoro
- compound
- alkoxy
- tolyl
- carbon atoms
- Prior art date
Links
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 title claims abstract description 89
- 239000004009 herbicide Substances 0.000 title claims abstract description 26
- 150000001875 compounds Chemical class 0.000 claims abstract description 105
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 32
- 239000001257 hydrogen Substances 0.000 claims abstract description 32
- 239000000460 chlorine Substances 0.000 claims abstract description 25
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 22
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 21
- -1 carbalkoxy Chemical group 0.000 claims abstract description 20
- 150000002367 halogens Chemical group 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 150000002989 phenols Chemical class 0.000 claims abstract description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 12
- 125000001424 substituent group Chemical group 0.000 claims abstract description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 10
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 8
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 6
- 239000011591 potassium Substances 0.000 claims abstract description 6
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims abstract description 5
- 125000003277 amino group Chemical group 0.000 claims abstract description 5
- 159000000000 sodium salts Chemical class 0.000 claims abstract description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract 6
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract 3
- 150000002431 hydrogen Chemical group 0.000 claims abstract 3
- 239000000203 mixture Substances 0.000 claims description 51
- 238000000034 method Methods 0.000 claims description 46
- 241000196324 Embryophyta Species 0.000 claims description 43
- 150000003839 salts Chemical group 0.000 claims description 37
- 230000002363 herbicidal effect Effects 0.000 claims description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 238000002360 preparation method Methods 0.000 claims description 26
- 238000012360 testing method Methods 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- 239000001963 growth medium Substances 0.000 claims description 14
- 239000007795 chemical reaction product Substances 0.000 claims description 13
- 150000005171 halobenzenes Chemical class 0.000 claims description 13
- 230000009418 agronomic effect Effects 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 244000105624 Arachis hypogaea Species 0.000 claims description 6
- 229920000742 Cotton Polymers 0.000 claims description 6
- 244000000626 Daucus carota Species 0.000 claims description 6
- 235000010469 Glycine max Nutrition 0.000 claims description 6
- 244000068988 Glycine max Species 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 235000020232 peanut Nutrition 0.000 claims description 6
- 235000003255 Carthamus tinctorius Nutrition 0.000 claims description 4
- 244000020518 Carthamus tinctorius Species 0.000 claims description 4
- 235000002767 Daucus carota Nutrition 0.000 claims description 4
- 241000219146 Gossypium Species 0.000 claims description 4
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 239000004593 Epoxy Substances 0.000 claims description 3
- 239000000853 adhesive Substances 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- 235000010627 Phaseolus vulgaris Nutrition 0.000 claims description 2
- 244000046052 Phaseolus vulgaris Species 0.000 claims description 2
- 235000010582 Pisum sativum Nutrition 0.000 claims description 2
- 240000004713 Pisum sativum Species 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 235000013339 cereals Nutrition 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
- 230000000802 nitrating effect Effects 0.000 claims 2
- 238000006396 nitration reaction Methods 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 125000004953 trihalomethyl group Chemical group 0.000 abstract description 4
- 125000005113 hydroxyalkoxy group Chemical group 0.000 abstract description 2
- 125000005111 carboxyalkoxy group Chemical group 0.000 abstract 1
- 125000004181 carboxyalkyl group Chemical group 0.000 abstract 1
- 125000005117 dialkylcarbamoyl group Chemical group 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 101
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 73
- 239000000243 solution Substances 0.000 description 70
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 66
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 60
- 239000002904 solvent Substances 0.000 description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical class O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- 239000003921 oil Substances 0.000 description 14
- 235000019198 oils Nutrition 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 13
- 239000000047 product Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
- 240000007594 Oryza sativa Species 0.000 description 9
- 235000007164 Oryza sativa Nutrition 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 235000009566 rice Nutrition 0.000 description 9
- 239000002689 soil Substances 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- 235000007320 Avena fatua Nutrition 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- GETTZEONDQJALK-UHFFFAOYSA-N trifluorotoluene Substances FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 8
- 235000005853 Cyperus esculentus Nutrition 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 7
- 229960004592 isopropanol Drugs 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- 240000006995 Abutilon theophrasti Species 0.000 description 6
- 240000006122 Chenopodium album Species 0.000 description 6
- 235000009344 Chenopodium album Nutrition 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- 244000058871 Echinochloa crus-galli Species 0.000 description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 240000003768 Solanum lycopersicum Species 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 229910017604 nitric acid Inorganic materials 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
- 241000209140 Triticum Species 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
- 240000008042 Zea mays Species 0.000 description 5
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 5
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 5
- NUFNQYOELLVIPL-UHFFFAOYSA-N acifluorfen Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 NUFNQYOELLVIPL-UHFFFAOYSA-N 0.000 description 5
- 235000005822 corn Nutrition 0.000 description 5
- 229960004756 ethanol Drugs 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical compound [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- XILPLWOGHPSJBK-UHFFFAOYSA-N 1,2-dichloro-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(Cl)C(Cl)=C1 XILPLWOGHPSJBK-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 244000036975 Ambrosia artemisiifolia Species 0.000 description 4
- 241000209764 Avena fatua Species 0.000 description 4
- 244000075850 Avena orientalis Species 0.000 description 4
- 241000219198 Brassica Species 0.000 description 4
- 235000011331 Brassica Nutrition 0.000 description 4
- 235000011292 Brassica rapa Nutrition 0.000 description 4
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 4
- 241001148727 Bromus tectorum Species 0.000 description 4
- 241000217446 Calystegia sepium Species 0.000 description 4
- 241000207894 Convolvulus arvensis Species 0.000 description 4
- 244000285774 Cyperus esculentus Species 0.000 description 4
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 4
- 240000003176 Digitaria ciliaris Species 0.000 description 4
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 4
- 235000005476 Digitaria cruciata Nutrition 0.000 description 4
- 235000006830 Digitaria didactyla Nutrition 0.000 description 4
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 4
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- 235000014716 Eleusine indica Nutrition 0.000 description 4
- 241000209510 Liliopsida Species 0.000 description 4
- 240000004284 Rumex crispus Species 0.000 description 4
- 235000021501 Rumex crispus Nutrition 0.000 description 4
- 235000015422 Rumex crispus ssp. crispus Nutrition 0.000 description 4
- 235000015426 Rumex crispus ssp. fauriei Nutrition 0.000 description 4
- 244000207667 Rumex vesicarius Species 0.000 description 4
- 240000007807 Sisymbrium officinale Species 0.000 description 4
- 235000005373 Uvularia sessilifolia Nutrition 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 244000013123 dwarf bean Species 0.000 description 4
- 235000005489 dwarf bean Nutrition 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000003337 fertilizer Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 230000000885 phytotoxic effect Effects 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- NJDSBHJSXKXNMI-UHFFFAOYSA-N 1,2-dimethyl-3-phenoxybenzene Chemical compound CC1=CC=CC(OC=2C=CC=CC=2)=C1C NJDSBHJSXKXNMI-UHFFFAOYSA-N 0.000 description 3
- MWAGUKZCDDRDCS-UHFFFAOYSA-N 1-nitro-4-(4-nitrophenoxy)benzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C([N+]([O-])=O)C=C1 MWAGUKZCDDRDCS-UHFFFAOYSA-N 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 3
- 244000052363 Cynodon dactylon Species 0.000 description 3
- 244000075634 Cyperus rotundus Species 0.000 description 3
- 241000508725 Elymus repens Species 0.000 description 3
- 235000003403 Limnocharis flava Nutrition 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 240000002439 Sorghum halepense Species 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 230000000295 complement effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 230000009969 flowable effect Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000010899 nucleation Methods 0.000 description 3
- 238000003359 percent control normalization Methods 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- IWSFMWPETWIRHF-UHFFFAOYSA-N 1-[2-[2-(2,3-dimethylphenyl)-4-nitrophenoxy]-5-nitrophenyl]-2,3-dimethylbenzene Chemical compound C1=C(C(=C(C=C1)C1=C(C=CC(=C1)[N+](=O)[O-])OC1=C(C=C(C=C1)[N+](=O)[O-])C1=C(C(=CC=C1)C)C)C)C IWSFMWPETWIRHF-UHFFFAOYSA-N 0.000 description 2
- XVIRIXVOLLJIPF-UHFFFAOYSA-N 1-nitro-2-(2-nitrophenoxy)benzene Chemical compound [O-][N+](=O)C1=CC=CC=C1OC1=CC=CC=C1[N+]([O-])=O XVIRIXVOLLJIPF-UHFFFAOYSA-N 0.000 description 2
- QIJIUJYANDSEKG-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-amine Chemical compound CC(C)(C)CC(C)(C)N QIJIUJYANDSEKG-UHFFFAOYSA-N 0.000 description 2
- 240000001592 Amaranthus caudatus Species 0.000 description 2
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 2
- 235000004135 Amaranthus viridis Nutrition 0.000 description 2
- 235000003133 Ambrosia artemisiifolia Nutrition 0.000 description 2
- 235000003129 Ambrosia artemisiifolia var elatior Nutrition 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 235000005484 Chenopodium berlandieri Nutrition 0.000 description 2
- 235000009332 Chenopodium rubrum Nutrition 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 235000009849 Cucumis sativus Nutrition 0.000 description 2
- 240000008067 Cucumis sativus Species 0.000 description 2
- 235000002206 Daucus carota subsp carota Nutrition 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000192043 Echinochloa Species 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
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- 240000001549 Ipomoea eriocarpa Species 0.000 description 2
- 235000005146 Ipomoea eriocarpa Nutrition 0.000 description 2
- 241000209082 Lolium Species 0.000 description 2
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- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 2
- 235000012629 Mentha aquatica Nutrition 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 240000000275 Persicaria hydropiper Species 0.000 description 2
- 235000017337 Persicaria hydropiper Nutrition 0.000 description 2
- 241000978467 Persicaria pensylvanica Species 0.000 description 2
- 235000004442 Polygonum persicaria Nutrition 0.000 description 2
- 241000533293 Sesbania emerus Species 0.000 description 2
- 244000062793 Sorghum vulgare Species 0.000 description 2
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 241001506766 Xanthium Species 0.000 description 2
- 244000067505 Xanthium strumarium Species 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 235000003484 annual ragweed Nutrition 0.000 description 2
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- 238000009835 boiling Methods 0.000 description 2
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- 235000003488 common ragweed Nutrition 0.000 description 2
- 244000038559 crop plants Species 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 241001233957 eudicotyledons Species 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 235000019713 millet Nutrition 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229910003446 platinum oxide Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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- 239000002244 precipitate Substances 0.000 description 2
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- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
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- 239000012895 dilution Substances 0.000 description 1
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- ARFLASKVLJTEJD-UHFFFAOYSA-N ethyl 2-bromopropanoate Chemical compound CCOC(=O)C(C)Br ARFLASKVLJTEJD-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
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- 229910052806 inorganic carbonate Inorganic materials 0.000 description 1
- 229910052909 inorganic silicate Inorganic materials 0.000 description 1
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- FNFZPRQJSDRYOH-UHFFFAOYSA-N methyl 3-chloro-4-[2-[2-(2-chloro-4-methoxycarbonylphenyl)-4-nitrophenoxy]-5-nitrophenyl]benzoate Chemical compound ClC1=CC(C(=O)OC)=CC=C1C1=CC([N+]([O-])=O)=CC=C1OC1=CC=C([N+]([O-])=O)C=C1C1=CC=C(C(=O)OC)C=C1Cl FNFZPRQJSDRYOH-UHFFFAOYSA-N 0.000 description 1
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 1
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- 150000004950 naphthalene Chemical class 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000000575 pesticide 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
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- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
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- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- ILUJNXBVWGPCKH-UHFFFAOYSA-M potassium;3-ethoxy-4-nitrophenolate Chemical compound [K+].CCOC1=CC([O-])=CC=C1[N+]([O-])=O ILUJNXBVWGPCKH-UHFFFAOYSA-M 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
- VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
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- 150000004760 silicates Chemical class 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- RVULBHWZFCBODE-UHFFFAOYSA-M sodium;5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate Chemical compound [Na+].C1=C([N+]([O-])=O)C(C(=O)[O-])=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 RVULBHWZFCBODE-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
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- 239000000126 substance Substances 0.000 description 1
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- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
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- 150000003918 triazines Chemical class 0.000 description 1
- WCLDITPGPXSPGV-UHFFFAOYSA-N tricamba Chemical compound COC1=C(Cl)C=C(Cl)C(Cl)=C1C(O)=O WCLDITPGPXSPGV-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/07—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
- C07C205/11—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings
- C07C205/12—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings the six-membered aromatic ring or a condensed ring system containing that ring being substituted by halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/38—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. nitrodiphenyl ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/39—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups
- C07C205/42—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups having nitro groups or esterified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/43—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups having nitro groups or esterified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
-
- 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
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
- C07C275/34—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C275/36—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with at least one of the oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. N-aryloxyphenylureas
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
-
- 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
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/62—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by introduction of halogen; by substitution of halogen atoms by other halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23465172A | 1972-03-14 | 1972-03-14 | |
| US234656A US3888932A (en) | 1972-03-14 | 1972-03-14 | Herbicidal 4-trifluoromethyl-4-nitrodiphenyl ethers |
| US05/331,947 US4076741A (en) | 1972-03-14 | 1973-02-12 | Herbicidal 4-trifluoromethyl-4-nitrodiphenyl ethers |
| US331719A US3928416A (en) | 1972-03-14 | 1973-02-12 | Herbicidal 4-trifluoromethyl-4{40 nitrodiphenyl ethers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL41766A0 IL41766A0 (en) | 1973-05-31 |
| IL41766A true IL41766A (en) | 1977-04-29 |
Family
ID=27499755
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL41766A IL41766A (en) | 1972-03-14 | 1973-03-13 | Diphenyl ethers and their use as herbicides |
Country Status (21)
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE32216E (en) * | 1969-04-25 | 1986-07-29 | Rhone-Poulenc Agrochimie | Salts of substituted phenoxybenzoic acids, compositions of the same and herbicidal use thereof |
| USRE32243E (en) * | 1969-04-25 | 1986-09-09 | Rhone-Poulenc Agrochimie | Esters of substituted phenoxybenzoic acids, compositions of the same and herbicidal use thereof |
| USRE32215E (en) * | 1971-02-11 | 1986-07-22 | Rhone-Poulenc Agrochimie | Substituted phenoxybenzoic acids compositions of the same and herbicidal use thereof |
| JPS5436209B2 (enrdf_load_stackoverflow) * | 1972-10-24 | 1979-11-08 | ||
| EG11593A (en) * | 1973-07-03 | 1980-07-31 | Bayer Ag | Halogenated 4-trifluiromethyl-4-cyano-diphenyl-ethers process for their preparation and their use as herbicides |
| JPS5724761B2 (enrdf_load_stackoverflow) * | 1973-12-19 | 1982-05-26 | ||
| JPS5068800U (enrdf_load_stackoverflow) * | 1973-10-22 | 1975-06-19 | ||
| JPS50123824A (enrdf_load_stackoverflow) * | 1974-03-15 | 1975-09-29 | ||
| JPS50132125A (enrdf_load_stackoverflow) * | 1974-04-12 | 1975-10-20 | ||
| JPS5173126A (ja) * | 1974-12-23 | 1976-06-24 | Mitsui Toatsu Chemicals | Satsusozai |
| JPS545033A (en) * | 1977-06-15 | 1979-01-16 | Mitsui Toatsu Chem Inc | Herbicides |
| DE2938595A1 (de) * | 1979-09-24 | 1981-04-23 | Celamerck Gmbh & Co Kg, 6507 Ingelheim | Verfahren zur herstellung von diphenylaethern |
| DE2942930A1 (de) * | 1979-10-24 | 1981-05-27 | Basf Ag, 6700 Ludwigshafen | Substituierte harnstoffe, deren herstellung und verwendung als herbizide |
| DE3045805A1 (de) | 1980-12-05 | 1982-07-08 | Basf Ag, 6700 Ludwigshafen | Diphenylether, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| GB2105715B (en) * | 1981-08-07 | 1985-09-04 | Ciba Geigy Ag | Herbicidal phenoxyphenylamino acid derivatives |
| JP2801181B2 (ja) * | 1983-01-10 | 1998-09-21 | キヤノン株式会社 | シート反転装置 |
| FR2549047B1 (fr) * | 1983-07-12 | 1986-03-21 | Rhone Poulenc Agrochimie | Nouveaux herbicides derives d'acides aryloxybenzenes carbonimides |
| CA1274843A (en) * | 1984-05-18 | 1990-10-02 | Yoshiharu Hayashi | 2-nitro-5-(2'-chloro-4'- trifluoromethylphenoxy)phenylacetic ester, thioester and amide, process for preparation thereof, herbicidal composition, and method for destruction of undesirable weeds |
| HU193466B (en) * | 1984-11-12 | 1987-10-28 | Budapesti Vegyimuevek | Fungicidal composition comprising 2-nitrobenzoic acid derivative as active substance |
| JPS63157065U (enrdf_load_stackoverflow) * | 1987-04-02 | 1988-10-14 | ||
| DE69902987T2 (de) * | 1998-12-23 | 2003-01-23 | Dow Agrosciences Llc, Indianapolis | Herstellung von Diphenylethern |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1602719A (en) * | 1968-11-22 | 1971-01-18 | Herbicidal diphenylether/pheny urea compos - ition |
-
1973
- 1973-02-27 SE SE7302765A patent/SE416544B/xx unknown
- 1973-03-13 PH PH14420A patent/PH18682A/en unknown
- 1973-03-13 OA OA54853A patent/OA04348A/xx unknown
- 1973-03-13 CH CH363173A patent/CH567359A5/xx not_active IP Right Cessation
- 1973-03-13 IL IL41766A patent/IL41766A/en unknown
- 1973-03-13 DK DK136973A patent/DK144561C/da not_active IP Right Cessation
- 1973-03-13 SU SU731898369A patent/SU713520A3/ru active
- 1973-03-13 GB GB1195473A patent/GB1423376A/en not_active Expired
- 1973-03-13 FR FR7308925A patent/FR2175997B1/fr not_active Expired
- 1973-03-13 HU HU73RO00000709A patent/HU172709B/hu unknown
- 1973-03-13 LU LU67204A patent/LU67204A1/xx unknown
- 1973-03-13 AR AR247014A patent/AR208495A1/es active
- 1973-03-14 AU AU53289/73A patent/AU467605B2/en not_active Expired
- 1973-03-14 NL NLAANVRAGE7303590,A patent/NL174825C/xx not_active IP Right Cessation
- 1973-03-14 RO RO7374159A patent/RO77037A/ro unknown
- 1973-03-14 JP JP48029896A patent/JPS5825641B2/ja not_active Expired
- 1973-03-14 TR TR18291A patent/TR18291A/xx unknown
- 1973-03-14 IT IT21605/73A patent/IT983545B/it active
- 1973-03-14 IE IE415/73A patent/IE37575B1/xx unknown
- 1973-03-16 IN IN598/CAL/73A patent/IN138701B/en unknown
-
1977
- 1977-05-11 KE KE2734A patent/KE2734A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE37575B1 (en) | 1977-08-31 |
| IT983545B (it) | 1974-11-11 |
| HU172709B (hu) | 1978-11-28 |
| NL7303590A (enrdf_load_stackoverflow) | 1973-09-18 |
| FR2175997A1 (enrdf_load_stackoverflow) | 1973-10-26 |
| PH18682A (en) | 1985-08-29 |
| SU713520A3 (ru) | 1980-01-30 |
| JPS49236A (enrdf_load_stackoverflow) | 1974-01-05 |
| IN138701B (enrdf_load_stackoverflow) | 1976-03-20 |
| OA04348A (fr) | 1980-01-31 |
| IL41766A0 (en) | 1973-05-31 |
| NL174825B (nl) | 1984-03-16 |
| CH567359A5 (enrdf_load_stackoverflow) | 1975-10-15 |
| DK144561B (da) | 1982-03-29 |
| LU67204A1 (enrdf_load_stackoverflow) | 1973-09-14 |
| DK144561C (da) | 1982-09-20 |
| AR208495A1 (es) | 1977-02-15 |
| AU467605B2 (en) | 1975-12-04 |
| AU5328973A (en) | 1974-09-19 |
| JPS5825641B2 (ja) | 1983-05-28 |
| RO77037A (ro) | 1981-08-30 |
| NL174825C (nl) | 1984-08-16 |
| KE2734A (en) | 1977-05-27 |
| FR2175997B1 (enrdf_load_stackoverflow) | 1977-02-04 |
| IE37575L (en) | 1973-09-14 |
| TR18291A (tr) | 1976-12-28 |
| GB1423376A (en) | 1976-02-04 |
| SE416544B (sv) | 1981-01-19 |
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