DE2311897A1 - N-substituierte n-phenylamine und herbicide mittel - Google Patents
N-substituierte n-phenylamine und herbicide mittelInfo
- Publication number
- DE2311897A1 DE2311897A1 DE2311897A DE2311897A DE2311897A1 DE 2311897 A1 DE2311897 A1 DE 2311897A1 DE 2311897 A DE2311897 A DE 2311897A DE 2311897 A DE2311897 A DE 2311897A DE 2311897 A1 DE2311897 A1 DE 2311897A1
- Authority
- DE
- Germany
- Prior art keywords
- ethyl ester
- chloroacetyl
- glycine ethyl
- glycine
- ester
- 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.)
- Ceased
Links
- 239000004009 herbicide Substances 0.000 title claims abstract description 33
- 150000001448 anilines Chemical class 0.000 title description 2
- -1 carboxy ester Chemical class 0.000 claims abstract description 77
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 4
- 150000002148 esters Chemical class 0.000 claims description 41
- 230000000885 phytotoxic effect Effects 0.000 claims description 37
- 231100000208 phytotoxic Toxicity 0.000 claims description 36
- 239000000463 material Substances 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 150000005840 aryl radicals Chemical class 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 2
- XEVRDFDBXJMZFG-UHFFFAOYSA-N carbonyl dihydrazine Chemical compound NNC(=O)NN XEVRDFDBXJMZFG-UHFFFAOYSA-N 0.000 claims 1
- 239000004576 sand Substances 0.000 claims 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract description 24
- 239000002253 acid Substances 0.000 abstract description 5
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 abstract description 4
- FOYHNROGBXVLLX-UHFFFAOYSA-N 2,6-diethylaniline Chemical compound CCC1=CC=CC(CC)=C1N FOYHNROGBXVLLX-UHFFFAOYSA-N 0.000 abstract description 2
- 125000001118 alkylidene group Chemical group 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- SDZXZKJIYVWFBZ-UHFFFAOYSA-N 2-(2,6-diethylanilino)acetic acid Chemical compound CCC1=CC=CC(CC)=C1NCC(O)=O SDZXZKJIYVWFBZ-UHFFFAOYSA-N 0.000 abstract 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 abstract 1
- SOWBFZRMHSNYGE-UHFFFAOYSA-N Monoamide-Oxalic acid Natural products NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 47
- 239000000203 mixture Substances 0.000 description 41
- 230000006378 damage Effects 0.000 description 26
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 description 24
- 239000005573 Linuron Substances 0.000 description 22
- 241000219198 Brassica Species 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 20
- YGLMVCVJLXREAK-UHFFFAOYSA-N Noruron Chemical compound C12CCCC2C2CC(NC(=O)N(C)C)C1C2 YGLMVCVJLXREAK-UHFFFAOYSA-N 0.000 description 19
- 235000010469 Glycine max Nutrition 0.000 description 18
- 230000002363 herbicidal effect Effects 0.000 description 18
- 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 15
- 244000062793 Sorghum vulgare Species 0.000 description 15
- 239000003795 chemical substances by application Substances 0.000 description 15
- 239000002689 soil Substances 0.000 description 15
- 235000003351 Brassica cretica Nutrition 0.000 description 14
- 235000003343 Brassica rupestris Nutrition 0.000 description 14
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 14
- NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 14
- 235000019713 millet Nutrition 0.000 description 14
- 235000010460 mustard Nutrition 0.000 description 14
- 239000005510 Diuron Substances 0.000 description 13
- RZILCCPWPBTYDO-UHFFFAOYSA-N fluometuron Chemical compound CN(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 RZILCCPWPBTYDO-UHFFFAOYSA-N 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- 210000002268 wool Anatomy 0.000 description 12
- WFKSADNZWSKCRZ-UHFFFAOYSA-N Diethatyl-ethyl Chemical compound CCOC(=O)CN(C(=O)CCl)C1=C(CC)C=CC=C1CC WFKSADNZWSKCRZ-UHFFFAOYSA-N 0.000 description 11
- 239000005533 Fluometuron Substances 0.000 description 11
- 239000004480 active ingredient Substances 0.000 description 11
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 11
- WYKYKTKDBLFHCY-UHFFFAOYSA-N chloridazon Chemical compound O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1 WYKYKTKDBLFHCY-UHFFFAOYSA-N 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 230000002195 synergetic effect Effects 0.000 description 11
- 239000005493 Chloridazon (aka pyrazone) Substances 0.000 description 10
- 235000017896 Digitaria Nutrition 0.000 description 10
- 241001303487 Digitaria <clam> Species 0.000 description 10
- 241000209219 Hordeum Species 0.000 description 10
- 235000005775 Setaria Nutrition 0.000 description 10
- 241000232088 Setaria <nematode> Species 0.000 description 10
- UHJMECPUUCQFRL-UHFFFAOYSA-N ethyl 2-(2,6-diethylanilino)acetate Chemical compound CCOC(=O)CNC1=C(CC)C=CC=C1CC UHJMECPUUCQFRL-UHFFFAOYSA-N 0.000 description 10
- 230000012010 growth Effects 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 241000743985 Alopecurus Species 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 244000068988 Glycine max Species 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- 229910052708 sodium Inorganic materials 0.000 description 9
- 241000219318 Amaranthus Species 0.000 description 8
- 244000058871 Echinochloa crus-galli Species 0.000 description 8
- 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 8
- 235000013399 edible fruits Nutrition 0.000 description 8
- XXOYNJXVWVNOOJ-UHFFFAOYSA-N fenuron Chemical compound CN(C)C(=O)NC1=CC=CC=C1 XXOYNJXVWVNOOJ-UHFFFAOYSA-N 0.000 description 8
- 230000035784 germination Effects 0.000 description 8
- 235000011331 Brassica Nutrition 0.000 description 7
- 241000219146 Gossypium Species 0.000 description 7
- 150000003863 ammonium salts Chemical class 0.000 description 7
- 239000012876 carrier material Substances 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 235000011999 Panicum crusgalli Nutrition 0.000 description 6
- 240000004713 Pisum sativum Species 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 125000004494 ethyl ester group Chemical group 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 244000075850 Avena orientalis Species 0.000 description 5
- 241001148727 Bromus tectorum Species 0.000 description 5
- 244000037364 Cinnamomum aromaticum Species 0.000 description 5
- 235000014489 Cinnamomum aromaticum Nutrition 0.000 description 5
- 241001547427 Cissampelos pareira Species 0.000 description 5
- 235000021506 Ipomoea Nutrition 0.000 description 5
- 241000207783 Ipomoea Species 0.000 description 5
- 241000209082 Lolium Species 0.000 description 5
- 235000010582 Pisum sativum Nutrition 0.000 description 5
- 241000209140 Triticum Species 0.000 description 5
- 230000017066 negative regulation of growth Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 240000001592 Amaranthus caudatus Species 0.000 description 4
- 235000005781 Avena Nutrition 0.000 description 4
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 4
- 240000006122 Chenopodium album Species 0.000 description 4
- 235000009344 Chenopodium album Nutrition 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 4
- 244000046052 Phaseolus vulgaris Species 0.000 description 4
- 241000209504 Poaceae Species 0.000 description 4
- 240000005498 Setaria italica Species 0.000 description 4
- 240000006410 Sida spinosa Species 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 235000021536 Sugar beet Nutrition 0.000 description 4
- 235000021307 Triticum Nutrition 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- 230000002147 killing effect Effects 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- ISERORSDFSDMDV-UHFFFAOYSA-N 2-(n-(2-chloroacetyl)-2,6-diethylanilino)acetic acid Chemical compound CCC1=CC=CC(CC)=C1N(CC(O)=O)C(=O)CCl ISERORSDFSDMDV-UHFFFAOYSA-N 0.000 description 3
- UGIUIFDIFSBIBH-UHFFFAOYSA-N 2-(n-(2-chloroacetyl)-2,6-dimethylanilino)acetic acid Chemical compound CC1=CC=CC(C)=C1N(CC(O)=O)C(=O)CCl UGIUIFDIFSBIBH-UHFFFAOYSA-N 0.000 description 3
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 3
- 244000105624 Arachis hypogaea Species 0.000 description 3
- 235000016068 Berberis vulgaris Nutrition 0.000 description 3
- 241000335053 Beta vulgaris Species 0.000 description 3
- 241000367098 Brassica juncea var. crispifolia Species 0.000 description 3
- 244000025254 Cannabis sativa Species 0.000 description 3
- 241001111317 Chondrodendron tomentosum Species 0.000 description 3
- 240000008853 Datura stramonium Species 0.000 description 3
- 241000221079 Euphorbia <genus> Species 0.000 description 3
- 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 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 235000007226 Setaria italica Nutrition 0.000 description 3
- 235000002248 Setaria viridis Nutrition 0.000 description 3
- 240000003461 Setaria viridis Species 0.000 description 3
- 235000010086 Setaria viridis var. viridis Nutrition 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000295 complement effect Effects 0.000 description 3
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- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- WOKGGLSYQGJYTP-UHFFFAOYSA-N 2-(n-(2-chloroacetyl)-2-ethyl-6-methylanilino)acetic acid Chemical compound CCC1=CC=CC(C)=C1N(CC(O)=O)C(=O)CCl WOKGGLSYQGJYTP-UHFFFAOYSA-N 0.000 description 2
- XOJVHLIYNSOZOO-SWOBOCGESA-N Arctiin Chemical compound C1=C(OC)C(OC)=CC=C1C[C@@H]1[C@@H](CC=2C=C(OC)C(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)=CC=2)C(=O)OC1 XOJVHLIYNSOZOO-SWOBOCGESA-N 0.000 description 2
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- 235000008078 Arctium minus Nutrition 0.000 description 2
- 235000021537 Beetroot Nutrition 0.000 description 2
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
- 241000208296 Datura Species 0.000 description 2
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- 239000004471 Glycine Substances 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 241000736851 Tagetes Species 0.000 description 2
- 241001506766 Xanthium Species 0.000 description 2
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- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- JVVXZOOGOGPDRZ-SLFFLAALSA-N [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 JVVXZOOGOGPDRZ-SLFFLAALSA-N 0.000 description 2
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- 239000011575 calcium Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
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- 239000012141 concentrate Substances 0.000 description 2
- 235000008504 concentrate Nutrition 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
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- 230000000694 effects Effects 0.000 description 2
- BJMLEASNPFLBCM-UHFFFAOYSA-N ethyl 2-(2-chloro-N-(2-chloroacetyl)anilino)acetate Chemical compound CCOC(=O)CN(C(=O)CCl)C1=CC=CC=C1Cl BJMLEASNPFLBCM-UHFFFAOYSA-N 0.000 description 2
- MQEANDXMEBSQFW-UHFFFAOYSA-N ethyl 2-(3-chloro-n-(2-chloroacetyl)anilino)acetate Chemical compound CCOC(=O)CN(C(=O)CCl)C1=CC=CC(Cl)=C1 MQEANDXMEBSQFW-UHFFFAOYSA-N 0.000 description 2
- IKDFOURAARBLTD-UHFFFAOYSA-N ethyl 2-(4-chloro-n-(2-chloroacetyl)anilino)acetate Chemical compound CCOC(=O)CN(C(=O)CCl)C1=CC=C(Cl)C=C1 IKDFOURAARBLTD-UHFFFAOYSA-N 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
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- 125000006353 oxyethylene group Chemical group 0.000 description 2
- 229910052625 palygorskite Inorganic materials 0.000 description 2
- 235000020232 peanut Nutrition 0.000 description 2
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- 239000011591 potassium Substances 0.000 description 2
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
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- GQTSZOJDWDRDFP-UHFFFAOYSA-N 2-[[4-(trifluoromethyl)phenyl]azaniumyl]acetate Chemical compound OC(=O)CNC1=CC=C(C(F)(F)F)C=C1 GQTSZOJDWDRDFP-UHFFFAOYSA-N 0.000 description 1
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 1
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- 239000005995 Aluminium silicate Substances 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/10—Formation of amino groups in compounds containing carboxyl groups with simultaneously increasing the number of carbon atoms in the carbon skeleton
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/46—N-acyl derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/40—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to carbon atoms of at least one six-membered aromatic ring and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23381772A | 1972-03-10 | 1972-03-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2311897A1 true DE2311897A1 (de) | 1973-10-04 |
Family
ID=22878810
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2311897A Ceased DE2311897A1 (de) | 1972-03-10 | 1973-03-09 | N-substituierte n-phenylamine und herbicide mittel |
Country Status (13)
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4126440A (en) | 1976-03-09 | 1978-11-21 | Ciba-Geigy Corporation | Hydroxamic acid derivatives for regulating plant growth |
| US4165381A (en) * | 1975-09-30 | 1979-08-21 | Ciba-Geigy Corporation | Microbicidal compositions |
| DE2943019A1 (de) * | 1978-10-27 | 1980-05-08 | Ciba Geigy Ag | Mikrobizides mittel |
| US4349550A (en) * | 1975-09-30 | 1982-09-14 | Ciba-Geigy Corporation | Fungicidal N-(pyridazinoacetyl)-anilines |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4096167A (en) * | 1974-10-17 | 1978-06-20 | Chevron Research Company | Fungicidal and herbicidal alpha-haloacetanilides |
| JPS5240797U (enrdf_load_stackoverflow) * | 1975-09-16 | 1977-03-23 | ||
| JPS62105574U (enrdf_load_stackoverflow) * | 1985-12-24 | 1987-07-06 | ||
| DE3723071A1 (de) * | 1987-07-11 | 1989-01-19 | Bayer Ag | Verfahren zur isolierung von polyarylensulfiden |
| RU2260948C2 (ru) | 1999-11-17 | 2005-09-27 | Байер Акциенгезельшафт | Гербицидное средство |
-
1973
- 1973-01-02 CA CA000160332A patent/CA1257608A/en not_active Expired
- 1973-01-16 ZA ZA730316A patent/ZA73316B/xx unknown
- 1973-01-31 TR TR18384A patent/TR18384A/xx unknown
- 1973-02-05 AU AU51831/73A patent/AU476514B2/en not_active Expired
- 1973-02-21 JP JP48020314A patent/JPS49232A/ja active Pending
- 1973-03-02 AR AR246904A patent/AR203081A1/es active
- 1973-03-05 BE BE128358A patent/BE796263A/xx not_active IP Right Cessation
- 1973-03-09 AT AT208873A patent/AT339284B/de not_active IP Right Cessation
- 1973-03-09 IT IT21429/73A patent/IT981287B/it active
- 1973-03-09 DE DE2311897A patent/DE2311897A1/de not_active Ceased
- 1973-03-09 BR BR731703A patent/BR7301703D0/pt unknown
-
1975
- 1975-02-12 SE SE7501572A patent/SE411206B/xx unknown
- 1975-09-23 SE SE7510667A patent/SE7510667L/xx not_active Application Discontinuation
-
1978
- 1978-01-04 KR KR7800001A patent/KR800001698B1/ko not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4165381A (en) * | 1975-09-30 | 1979-08-21 | Ciba-Geigy Corporation | Microbicidal compositions |
| US4349550A (en) * | 1975-09-30 | 1982-09-14 | Ciba-Geigy Corporation | Fungicidal N-(pyridazinoacetyl)-anilines |
| US4126440A (en) | 1976-03-09 | 1978-11-21 | Ciba-Geigy Corporation | Hydroxamic acid derivatives for regulating plant growth |
| DE2943019A1 (de) * | 1978-10-27 | 1980-05-08 | Ciba Geigy Ag | Mikrobizides mittel |
| US4330556A (en) | 1978-10-27 | 1982-05-18 | Ciba-Geigy Corporation | Microbicidal N-1'-hydrocarbyloxycarbonylethyl)-N-alkoxyacetylanilines |
Also Published As
| Publication number | Publication date |
|---|---|
| AR203081A1 (es) | 1975-08-14 |
| IT981287B (it) | 1974-10-10 |
| SE7510667L (sv) | 1975-09-23 |
| AT339284B (de) | 1977-10-10 |
| ZA73316B (en) | 1973-10-31 |
| SE7501572L (enrdf_load_stackoverflow) | 1975-02-12 |
| AU476514B2 (en) | 1976-09-23 |
| CA1257608A (en) | 1989-07-18 |
| ATA208873A (de) | 1977-02-15 |
| JPS49232A (enrdf_load_stackoverflow) | 1974-01-05 |
| SE411206B (sv) | 1979-12-10 |
| AU5183173A (en) | 1974-08-08 |
| TR18384A (tr) | 1977-05-01 |
| BE796263A (fr) | 1973-07-02 |
| BR7301703D0 (pt) | 1974-07-11 |
| KR800001698B1 (ko) | 1980-12-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8131 | Rejection |