DE2229211A1 - N-Acetonitrilo-alpha-phenoxyalkylamide und ihre Verwendung als Herbizide - Google Patents
N-Acetonitrilo-alpha-phenoxyalkylamide und ihre Verwendung als HerbizideInfo
- Publication number
- DE2229211A1 DE2229211A1 DE19722229211 DE2229211A DE2229211A1 DE 2229211 A1 DE2229211 A1 DE 2229211A1 DE 19722229211 DE19722229211 DE 19722229211 DE 2229211 A DE2229211 A DE 2229211A DE 2229211 A1 DE2229211 A1 DE 2229211A1
- Authority
- DE
- Germany
- Prior art keywords
- radical
- carbon atoms
- formula
- ethyl
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000004009 herbicide Substances 0.000 title description 22
- 150000001875 compounds Chemical class 0.000 claims description 25
- -1 Alkyl radical Chemical group 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 26
- 230000006378 damage Effects 0.000 description 16
- 238000002360 preparation method Methods 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000007788 liquid Substances 0.000 description 11
- 239000004480 active ingredient Substances 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000007921 spray Substances 0.000 description 9
- 230000002363 herbicidal effect Effects 0.000 description 8
- 239000002270 dispersing agent Substances 0.000 description 7
- 239000002689 soil Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 244000046052 Phaseolus vulgaris Species 0.000 description 4
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000000428 dust Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 231100000208 phytotoxic Toxicity 0.000 description 3
- 230000000885 phytotoxic effect Effects 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 231100000167 toxic agent Toxicity 0.000 description 3
- 239000003440 toxic substance Substances 0.000 description 3
- 238000009736 wetting Methods 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- 244000075850 Avena orientalis Species 0.000 description 2
- 235000007319 Avena orientalis Nutrition 0.000 description 2
- 244000178993 Brassica juncea Species 0.000 description 2
- 235000011332 Brassica juncea Nutrition 0.000 description 2
- 235000014700 Brassica juncea var napiformis Nutrition 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 244000152970 Digitaria sanguinalis Species 0.000 description 2
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- 206010053759 Growth retardation Diseases 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 244000088461 Panicum crus-galli Species 0.000 description 2
- 235000011999 Panicum crusgalli Nutrition 0.000 description 2
- 235000021501 Rumex crispus Nutrition 0.000 description 2
- 244000207667 Rumex vesicarius Species 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 231100000001 growth retardation Toxicity 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
- 230000000051 modifying effect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 230000008635 plant growth Effects 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- SMYMJHWAQXWPDB-UHFFFAOYSA-N (2,4,5-trichlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC(Cl)=C(Cl)C=C1Cl SMYMJHWAQXWPDB-UHFFFAOYSA-N 0.000 description 1
- 239000003559 2,4,5-trichlorophenoxyacetic acid Substances 0.000 description 1
- UFWSTLURZCKNHB-UHFFFAOYSA-N 2-(3,5-dichlorophenoxy)butanoyl chloride Chemical compound CCC(C(Cl)=O)OC1=CC(Cl)=CC(Cl)=C1 UFWSTLURZCKNHB-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- 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 1
- WBEKRMVYCWRRDJ-UHFFFAOYSA-N 2-n-propan-2-yl-1,3,5-triazine-2,4-diamine Chemical compound CC(C)NC1=NC=NC(N)=N1 WBEKRMVYCWRRDJ-UHFFFAOYSA-N 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- VPOMSPZBQMDLTM-UHFFFAOYSA-N 3,5-dichlorophenol Chemical compound OC1=CC(Cl)=CC(Cl)=C1 VPOMSPZBQMDLTM-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 244000237956 Amaranthus retroflexus Species 0.000 description 1
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- HSSBORCLYSCBJR-UHFFFAOYSA-N Chloramben Chemical compound NC1=CC(Cl)=CC(C(O)=O)=C1Cl HSSBORCLYSCBJR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- DFCAFRGABIXSDS-UHFFFAOYSA-N Cycloate Chemical compound CCSC(=O)N(CC)C1CCCCC1 DFCAFRGABIXSDS-UHFFFAOYSA-N 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- GUVLYNGULCJVDO-UHFFFAOYSA-N EPTC Chemical compound CCCN(CCC)C(=O)SCC GUVLYNGULCJVDO-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 244000115721 Pennisetum typhoides Species 0.000 description 1
- 235000007195 Pennisetum typhoides Nutrition 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- OKUGPJPKMAEJOE-UHFFFAOYSA-N S-propyl dipropylcarbamothioate Chemical compound CCCSC(=O)N(CCC)CCC OKUGPJPKMAEJOE-UHFFFAOYSA-N 0.000 description 1
- 235000008515 Setaria glauca Nutrition 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000003869 acetamides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- 235000012216 bentonite Nutrition 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
- 230000033228 biological regulation Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- YYRMJZQKEFZXMX-UHFFFAOYSA-N calcium;phosphoric acid Chemical compound [Ca+2].OP(O)(O)=O.OP(O)(O)=O YYRMJZQKEFZXMX-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000011362 coarse particle Substances 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000002837 defoliant Substances 0.000 description 1
- 230000035613 defoliation Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 210000004262 dental pulp cavity Anatomy 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 208000037824 growth disorder Diseases 0.000 description 1
- 239000003864 humus Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 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 1
- 239000003350 kerosene Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000009526 moderate injury Effects 0.000 description 1
- OWSQEQYVIVEPSL-UHFFFAOYSA-N n-(3-methoxypropyl)-4-methylsulfanyl-1,3,5-triazin-2-amine Chemical compound COCCCNC1=NC=NC(SC)=N1 OWSQEQYVIVEPSL-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000010451 perlite Substances 0.000 description 1
- 235000019362 perlite Nutrition 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000002426 superphosphate Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 150000003918 triazines Chemical class 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
- 150000003672 ureas Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15705971A | 1971-06-25 | 1971-06-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2229211A1 true DE2229211A1 (de) | 1972-12-28 |
Family
ID=22562194
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722229211 Pending DE2229211A1 (de) | 1971-06-25 | 1972-06-15 | N-Acetonitrilo-alpha-phenoxyalkylamide und ihre Verwendung als Herbizide |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS4839631A (forum.php) |
| BE (1) | BE785325A (forum.php) |
| BR (1) | BR7204128D0 (forum.php) |
| CA (1) | CA992988A (forum.php) |
| CH (1) | CH562004A5 (forum.php) |
| DE (1) | DE2229211A1 (forum.php) |
| FR (1) | FR2143314B1 (forum.php) |
| GB (1) | GB1339244A (forum.php) |
| IL (1) | IL39746A (forum.php) |
| IT (1) | IT956775B (forum.php) |
| NL (1) | NL7208663A (forum.php) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3702964A1 (de) * | 1987-01-30 | 1988-08-11 | Shell Agrar Gmbh & Co Kg | Aryloxycarbonsaeurederivate, ihre herstellung und verwendung |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2446812A1 (fr) * | 1979-01-16 | 1980-08-14 | Produits Ind Cie Fse | Phenoxy- et thiophenoxynitriles et leurs applications en tant qu'herbicides |
| US5942640A (en) * | 1998-04-20 | 1999-08-24 | American Cyanamid Company | Process for the manufacture of N-(1-cyanoalkyl)-2-phenoxypropionamide derivatives |
-
1972
- 1972-04-27 CA CA140,736A patent/CA992988A/en not_active Expired
- 1972-05-04 GB GB2074672A patent/GB1339244A/en not_active Expired
- 1972-06-01 JP JP47053863A patent/JPS4839631A/ja active Pending
- 1972-06-15 DE DE19722229211 patent/DE2229211A1/de active Pending
- 1972-06-22 FR FR727222618A patent/FR2143314B1/fr not_active Expired
- 1972-06-22 CH CH938772A patent/CH562004A5/xx not_active IP Right Cessation
- 1972-06-22 IT IT26042/72A patent/IT956775B/it active
- 1972-06-23 BR BR4128/72A patent/BR7204128D0/pt unknown
- 1972-06-23 BE BE785325A patent/BE785325A/xx unknown
- 1972-06-23 NL NL7208663A patent/NL7208663A/xx unknown
- 1972-06-23 IL IL39746A patent/IL39746A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3702964A1 (de) * | 1987-01-30 | 1988-08-11 | Shell Agrar Gmbh & Co Kg | Aryloxycarbonsaeurederivate, ihre herstellung und verwendung |
Also Published As
| Publication number | Publication date |
|---|---|
| CA992988A (en) | 1976-07-13 |
| JPS4839631A (forum.php) | 1973-06-11 |
| IL39746A (en) | 1976-09-30 |
| NL7208663A (forum.php) | 1972-12-28 |
| BR7204128D0 (pt) | 1973-05-03 |
| IT956775B (it) | 1973-10-10 |
| BE785325A (fr) | 1972-12-27 |
| GB1339244A (en) | 1973-11-28 |
| FR2143314A1 (forum.php) | 1973-02-02 |
| CH562004A5 (forum.php) | 1975-05-30 |
| IL39746A0 (en) | 1972-08-30 |
| FR2143314B1 (forum.php) | 1973-07-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0048436A1 (de) | Herbizide Mittel | |
| DE2406475C2 (de) | 5-Acetamido-2,4-dimethyltrifluormethansulfonanilid und dessen landwirtschaftlich geeignete Salze, Verfahren zur Herstellung dieser Verbindungen und diese Verbindungen enthaltende Mittel | |
| CH644371A5 (de) | In 2- und 4-stellung disubstituierte 5-thiazolcarbonsaeuren und deren funktionelle derivate. | |
| DE2640484A1 (de) | Amidoxim-derivate, ihre herstellung und verwendung | |
| DE2804664A1 (de) | N- eckige klammer auf (phosphinyl) amino eckige klammer zu thio-methylcarbamate bzw. n- eckige klammer auf (phosphinothioyl) amino eckige klammer zu thio-methylcarbamate, deren verwendung in einem verfahren zur schaedlingsbekaempfung, pestizide mittel welche diese verbindungen enthalten, sowie verfahren zur herstellung dieser verbindungen und dafuer benoetigte ausgangsmaterialien | |
| DE2731960A1 (de) | Neue, im benzolring substituierte n-alkinyl-alpha-phenoxy-alkylamide und deren verwendung als herbicide | |
| DE2101938C2 (de) | 3-[2-Chlor-4-(3,3-dimethylureido)-phenyl]-5-tert.-butyl-1,3,4-oxadiazolon-(2), seine Herstellung und herbicide Zusammensetzungen, die es enthalten | |
| DE2628384A1 (de) | Herbizide und fungizide mittel | |
| DE2229211A1 (de) | N-Acetonitrilo-alpha-phenoxyalkylamide und ihre Verwendung als Herbizide | |
| DE2001770C3 (de) | Amidothionophosphorsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide | |
| DE2229062A1 (de) | N-alkyl-alpha-phenoxyalkylamide und ihre verwendung als herbizide | |
| DD262992A5 (de) | Nematizide und insektizide zusammensetzung | |
| DE2021822A1 (de) | Acylierte Triflourmethylharnstoffcarbamate und deren Verwendung als Herbizide | |
| DE1301819B (de) | Substituierte 2, 4-Diamino-6-chlor-s-triazine | |
| DE2017481A1 (de) | S-Alkyl-N-alkylbenzy!thiocarbamate und deren Verwendung als Herbizide | |
| DE2633159C2 (de) | Phosphorhaltige Verbindungen, Verfahren zu ihrer Herstellung, sowie diese Verbindungen enthaltende herbizide Mittel | |
| DE2415203A1 (de) | Alkyloxalylaminosubstituierte s-triazine sowie herbicide mittel | |
| DE3110452C2 (de) | 2-Chloracetanilide und sie enthaltende Herbizide | |
| DE2440868B2 (de) | Substituierte 3-Chloräthoxy-4-nitrodiphenyläther, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende herbizide Mittel | |
| DE3309141A1 (de) | Herbizide zusammensetzung | |
| DE2701108A1 (de) | N-(1,1-subst.-propinyl)-alpha(3,5-subst.-phenoxy)-alkylamide und ihre verwendung als herbizide | |
| DE3502629A1 (de) | Phenoxybenzoesaeurederivate, verfahren zu ihrer herstellung sowie ihre verwendung im pflanzenschutz | |
| DE2008601A1 (de) | Anilinoalkylthiocarboxamidverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als herbicide Mittel | |
| DE2014848A1 (de) | Isopropylidenaminoäthanolsalz von p-Nitrobenzolsulfonylharnstoff, seine Herstellung und Verwendung | |
| DE1542950C3 (de) | Substituierte Acetanilide, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende herbizide Mittel |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |