CA1164879A - 5-amino-1-phenylpyrazole-4-carboxylic acid esters, their preparation, herbicides containing these compounds and the use of these compounds as herbicides - Google Patents
5-amino-1-phenylpyrazole-4-carboxylic acid esters, their preparation, herbicides containing these compounds and the use of these compounds as herbicidesInfo
- Publication number
- CA1164879A CA1164879A CA000390754A CA390754A CA1164879A CA 1164879 A CA1164879 A CA 1164879A CA 000390754 A CA000390754 A CA 000390754A CA 390754 A CA390754 A CA 390754A CA 1164879 A CA1164879 A CA 1164879A
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- chlorine
- amino
- bromine
- acid
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 21
- BFMGSMOYBHOHGI-UHFFFAOYSA-N 5-amino-1-phenylpyrazole-4-carboxylic acid Chemical class NC1=C(C(O)=O)C=NN1C1=CC=CC=C1 BFMGSMOYBHOHGI-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 239000004009 herbicide Substances 0.000 title abstract description 10
- 238000002360 preparation method Methods 0.000 title description 6
- 239000000460 chlorine Chemical group 0.000 claims abstract description 70
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 41
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 31
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 19
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 18
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 18
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910052794 bromium Chemical group 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000011630 iodine Chemical group 0.000 claims abstract description 6
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims description 54
- -1 2-cyanoacrylic acid ester Chemical class 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 7
- 239000011707 mineral Substances 0.000 claims description 7
- 150000004031 phenylhydrazines Chemical class 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229940067157 phenylhydrazine Drugs 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- JANSGFWBVHIHKV-UHFFFAOYSA-N methyl 5-amino-1-(2,4,6-trichlorophenyl)pyrazole-4-carboxylate Chemical compound NC1=C(C(=O)OC)C=NN1C1=C(Cl)C=C(Cl)C=C1Cl JANSGFWBVHIHKV-UHFFFAOYSA-N 0.000 claims description 3
- 239000002689 soil Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000008635 plant growth Effects 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- VFIOOJVSVZPCLD-UHFFFAOYSA-N methyl 5-amino-1-(2,4,6-tribromophenyl)pyrazole-4-carboxylate Chemical compound NC1=C(C(=O)OC)C=NN1C1=C(Br)C=C(Br)C=C1Br VFIOOJVSVZPCLD-UHFFFAOYSA-N 0.000 claims 1
- SHRQTRLNCRQMCI-UHFFFAOYSA-N methyl 5-amino-1-(4-chloro-2-methylphenyl)pyrazole-4-carboxylate Chemical compound NC1=C(C(=O)OC)C=NN1C1=CC=C(Cl)C=C1C SHRQTRLNCRQMCI-UHFFFAOYSA-N 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 description 27
- 150000001408 amides Chemical class 0.000 description 18
- 241000196324 Embryophyta Species 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000004480 active ingredient Substances 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 10
- 230000002363 herbicidal effect Effects 0.000 description 10
- 238000011282 treatment Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 229940125904 compound 1 Drugs 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000006185 dispersion Substances 0.000 description 8
- 229920001651 Cyanoacrylate Polymers 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 159000000000 sodium salts Chemical class 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 244000038559 crop plants Species 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 235000010755 mineral Nutrition 0.000 description 5
- 241000894007 species Species 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 239000004359 castor oil Substances 0.000 description 4
- 229960001777 castor oil Drugs 0.000 description 4
- 235000019438 castor oil Nutrition 0.000 description 4
- 235000013339 cereals Nutrition 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 244000299507 Gossypium hirsutum Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
- 235000010582 Pisum sativum Nutrition 0.000 description 3
- 240000004713 Pisum sativum Species 0.000 description 3
- 241001506137 Rapa Species 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 150000003931 anilides Chemical class 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 235000008504 concentrate Nutrition 0.000 description 3
- 229960004756 ethanol Drugs 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 235000012054 meals Nutrition 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 150000002790 naphthalenes Chemical class 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- MULHANRBCQBHII-UHFFFAOYSA-N (2,4,6-trichlorophenyl)hydrazine Chemical compound NNC1=C(Cl)C=C(Cl)C=C1Cl MULHANRBCQBHII-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 244000105624 Arachis hypogaea Species 0.000 description 2
- 235000005340 Asparagus officinalis Nutrition 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- 235000021537 Beetroot Nutrition 0.000 description 2
- 241000335053 Beta vulgaris Species 0.000 description 2
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
- 240000002791 Brassica napus Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 240000007154 Coffea arabica Species 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 240000004658 Medicago sativa Species 0.000 description 2
- 235000004357 Mentha x piperita Nutrition 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 235000010617 Phaseolus lunatus Nutrition 0.000 description 2
- 235000002594 Solanum nigrum Nutrition 0.000 description 2
- 240000006394 Sorghum bicolor Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 235000015724 Trifolium pratense Nutrition 0.000 description 2
- 244000098338 Triticum aestivum Species 0.000 description 2
- 230000001464 adherent effect Effects 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 2
- 244000013123 dwarf bean Species 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 230000035784 germination Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- FYXVHJJZGRTONS-UHFFFAOYSA-N methyl 2-cyano-3-ethoxyprop-2-enoate Chemical compound CCOC=C(C#N)C(=O)OC FYXVHJJZGRTONS-UHFFFAOYSA-N 0.000 description 2
- IYFIUVAYAFAKRF-UHFFFAOYSA-N methyl 5-amino-1-(2,4-dichlorophenyl)pyrazole-4-carboxylate Chemical compound NC1=C(C(=O)OC)C=NN1C1=CC=C(Cl)C=C1Cl IYFIUVAYAFAKRF-UHFFFAOYSA-N 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 235000013526 red clover Nutrition 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- KAUORVXNCWRLGN-UHFFFAOYSA-N (2-ethoxy-3,3-dimethyl-2H-1-benzofuran-5-yl)methanesulfonic acid (2-ethoxy-3,3-dimethyl-2H-1-benzofuran-5-yl)methyl-methylsulfamic acid Chemical compound C(C)OC1OC2=C(C1(C)C)C=C(C=C2)CN(C)S(=O)(=O)O.C(C)OC2OC1=C(C2(C)C)C=C(C=C1)CS(=O)(=O)O KAUORVXNCWRLGN-UHFFFAOYSA-N 0.000 description 1
- DSVOTYIOPGIVPP-UHFFFAOYSA-N (3,4-dichlorophenyl)methyl n-methylcarbamate Chemical compound CNC(=O)OCC1=CC=C(Cl)C(Cl)=C1 DSVOTYIOPGIVPP-UHFFFAOYSA-N 0.000 description 1
- SODPIMGUZLOIPE-UHFFFAOYSA-N (4-chlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1 SODPIMGUZLOIPE-UHFFFAOYSA-N 0.000 description 1
- KKFBZUNYJMVNFV-UHFFFAOYSA-N 1,2-bis(2-methylpropyl)naphthalene Chemical compound C1=CC=CC2=C(CC(C)C)C(CC(C)C)=CC=C21 KKFBZUNYJMVNFV-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BKWVWXCIYKENIY-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(triazol-1-yl)butan-2-one Chemical compound C1=CN=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BKWVWXCIYKENIY-UHFFFAOYSA-N 0.000 description 1
- ALMRVRBXLAQTLI-UHFFFAOYSA-N 1-[1,1-dimethyl-4,6-di(propan-2-yl)-2,3-dihydroinden-5-yl]propan-1-one Chemical compound CCC(=O)C1=C(C(C)C)C=C2C(C)(C)CCC2=C1C(C)C ALMRVRBXLAQTLI-UHFFFAOYSA-N 0.000 description 1
- FKKAGFLIPSSCHT-UHFFFAOYSA-N 1-dodecoxydodecane;sulfuric acid Chemical compound OS(O)(=O)=O.CCCCCCCCCCCCOCCCCCCCCCCCC FKKAGFLIPSSCHT-UHFFFAOYSA-N 0.000 description 1
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
- UYGUFXUBSNDUFA-UHFFFAOYSA-N 2,3,5,6-tetrachlorobenzoic acid Chemical compound OC(=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl UYGUFXUBSNDUFA-UHFFFAOYSA-N 0.000 description 1
- XZIDTOHMJBOSOX-UHFFFAOYSA-N 2,3,6-TBA Chemical compound OC(=O)C1=C(Cl)C=CC(Cl)=C1Cl XZIDTOHMJBOSOX-UHFFFAOYSA-N 0.000 description 1
- YIVXMZJTEQBPQO-UHFFFAOYSA-N 2,4-DB Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1Cl YIVXMZJTEQBPQO-UHFFFAOYSA-N 0.000 description 1
- 239000002794 2,4-DB Substances 0.000 description 1
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
- HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 description 1
- QFUSCYRJMXLNRB-UHFFFAOYSA-N 2,6-dinitroaniline Chemical class NC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O QFUSCYRJMXLNRB-UHFFFAOYSA-N 0.000 description 1
- MZHCENGPTKEIGP-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1Cl MZHCENGPTKEIGP-UHFFFAOYSA-N 0.000 description 1
- OPQYFNRLWBWCST-UHFFFAOYSA-N 2-(2-chlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=CC=C1Cl OPQYFNRLWBWCST-UHFFFAOYSA-N 0.000 description 1
- YIGXGYDKDDWZLS-UHFFFAOYSA-N 2-(2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=CC=C1C YIGXGYDKDDWZLS-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
- WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 description 1
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 1
- ZFHPZZAFKVMMKO-UHFFFAOYSA-N 2-N,4-N-diethyl-6-methylsulfanyl-1,3,5-triazine-2,4-diamine 4-N-ethyl-6-methoxy-2-N-propan-2-yl-1,3,5-triazine-2,4-diamine 6-methylsulfanyl-2-N,4-N-di(propan-2-yl)-1,3,5-triazine-2,4-diamine Chemical compound CSC1=NC(=NC(=N1)NCC)NCC.COC1=NC(=NC(=N1)NCC)NC(C)C.CSC1=NC(=NC(=N1)NC(C)C)NC(C)C ZFHPZZAFKVMMKO-UHFFFAOYSA-N 0.000 description 1
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- REEXLQXWNOSJKO-UHFFFAOYSA-N 2h-1$l^{4},2,3-benzothiadiazine 1-oxide Chemical class C1=CC=C2S(=O)NN=CC2=C1 REEXLQXWNOSJKO-UHFFFAOYSA-N 0.000 description 1
- KRGRFGVRNPTIDU-UHFFFAOYSA-N 3,4-dimethyl-2,6-dinitro-n-pentan-3-ylaniline;n-ethyl-2,6-dinitro-n-propan-2-yl-4-(trifluoromethyl)aniline Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O.CCN(C(C)C)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O KRGRFGVRNPTIDU-UHFFFAOYSA-N 0.000 description 1
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 description 1
- LHDWHWWSGUHMTB-UHFFFAOYSA-N 3-(3-chloro-4-ethoxyphenyl)-1,1-dimethylurea O-ethyl 2-(4-chloro-2-methylphenoxy)ethanethioate Chemical compound CC1=C(OCC(=S)OCC)C=CC(=C1)Cl.ClC=1C=C(C=CC1OCC)NC(=O)N(C)C LHDWHWWSGUHMTB-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
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)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803045903 DE3045903A1 (de) | 1980-12-05 | 1980-12-05 | 5-amino-1-phenylpyrazol-4-carbonsaeureester, verfahren zu ihrer herstellung, diese enthaltende herbizide und ihre anwendung als herbizide |
| DEP3045903.1 | 1980-12-05 | ||
| DEP3126479.4 | 1981-07-04 | ||
| DE19813126479 DE3126479A1 (de) | 1981-07-04 | 1981-07-04 | 2'-phenylhydrazino-2-cyanacrylsaeureester, verfahren zu ihrer herstellung, diese enthaltende herbizide und ihre anwendung als herbizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1164879A true CA1164879A (en) | 1984-04-03 |
Family
ID=25789539
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000390754A Expired CA1164879A (en) | 1980-12-05 | 1981-11-24 | 5-amino-1-phenylpyrazole-4-carboxylic acid esters, their preparation, herbicides containing these compounds and the use of these compounds as herbicides |
| CA000390773A Expired CA1176271A (en) | 1980-12-05 | 1981-11-24 | 2'-phenylhydrazino-2-cyanoacrylic acid esters and herbicides containing these compounds |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000390773A Expired CA1176271A (en) | 1980-12-05 | 1981-11-24 | 2'-phenylhydrazino-2-cyanoacrylic acid esters and herbicides containing these compounds |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US4420324A (enEXAMPLES) |
| EP (2) | EP0053698B1 (enEXAMPLES) |
| AR (1) | AR229598A1 (enEXAMPLES) |
| AU (1) | AU7827681A (enEXAMPLES) |
| BR (2) | BR8107887A (enEXAMPLES) |
| CA (2) | CA1164879A (enEXAMPLES) |
| DD (2) | DD201091A5 (enEXAMPLES) |
| DE (2) | DE3168194D1 (enEXAMPLES) |
| DK (2) | DK537281A (enEXAMPLES) |
| GR (2) | GR75122B (enEXAMPLES) |
| IE (1) | IE51728B1 (enEXAMPLES) |
| IL (2) | IL64309A0 (enEXAMPLES) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MA19539A1 (fr) * | 1981-07-17 | 1983-04-01 | May & Baker Ltd | N Acylaminophenylpyrazoles |
| DE3420985A1 (de) * | 1983-10-15 | 1985-04-25 | Bayer Ag, 5090 Leverkusen | Substituierte 5-acylamino-1-phenylpyrazole |
| US4820335A (en) * | 1983-11-02 | 1989-04-11 | Hoechst Ag | 1-substituted imidazole-5-carboxylic acid derivatives, their preparation and their use as biocides |
| DE3402308A1 (de) * | 1984-01-24 | 1985-08-01 | Bayer Ag, 5090 Leverkusen | Herbizide mittel auf basis von pyrazolderivaten |
| DE3423582A1 (de) * | 1984-06-27 | 1986-01-09 | Bayer Ag, 5090 Leverkusen | Substituierte 5-acylamino-1-phenylpyrazole |
| DE3808896A1 (de) * | 1988-03-17 | 1989-09-28 | Hoechst Ag | Pflanzenschuetzende mittel auf basis von pyrazolcarbonsaeurederivaten |
| AU679735B2 (en) | 1993-04-07 | 1997-07-10 | Nissan Chemical Industries Ltd. | Pyrazole derivative |
| DE4429014A1 (de) | 1994-08-16 | 1996-02-22 | Basf Ag | Verfahren zur Herstellung von cyclischen Aminen |
| MX2022007686A (es) * | 2019-12-19 | 2022-07-19 | Bayer Ag | Acidos 1,5-difenilpirazolil-3-oxialquilicos y acidos 1-fenil-5-tienilpirazolil-3-oxialquilicos y su uso para el combate del crecimiento de plantas no deseado. |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2792296A (en) * | 1954-01-25 | 1957-05-14 | Monsanto Chemicals | Phenylhydrazinopropionitriles, herbicidal method and composition embodying same |
| GB854632A (en) * | 1956-02-10 | 1960-11-23 | Ciba Ltd | Manufacture of pyrazoles |
| US3187006A (en) * | 1956-04-17 | 1965-06-01 | Ciba Geigy Corp | N-substituted pyrazoles and method of preparing same |
| US3062635A (en) * | 1958-07-18 | 1962-11-06 | Du Pont | Method for inhibiting plant and fungal growth |
| US3515715A (en) * | 1967-01-23 | 1970-06-02 | Eastman Kodak Co | Quaternized pyrazolylazo dyes |
| US3567735A (en) * | 1967-10-03 | 1971-03-02 | Ciba Geigy Corp | Beta - (substituted-hydrazino) - alpha - cyano acrylic acids and derivatives,and process for preparing n-substituted pyrazoles |
| US3726662A (en) * | 1970-01-14 | 1973-04-10 | Monsanto Co | Herbicidal anilinomethylene-malononitriles |
| DE2747531A1 (de) * | 1977-10-22 | 1979-04-26 | Basf Ag | Substituierte 3-aminopyrazole |
| PT72563B (en) * | 1980-02-26 | 1982-02-11 | May & Baker Ltd | N-phenylpyrazole derivatives |
-
1981
- 1981-10-23 EP EP81108815A patent/EP0053698B1/de not_active Expired
- 1981-10-23 DE DE8181108815T patent/DE3168194D1/de not_active Expired
- 1981-10-23 GR GR66329A patent/GR75122B/el unknown
- 1981-10-23 EP EP81108816A patent/EP0053699B1/de not_active Expired
- 1981-10-23 GR GR66332A patent/GR74695B/el unknown
- 1981-10-23 DE DE8181108816T patent/DE3160972D1/de not_active Expired
- 1981-11-18 IL IL64309A patent/IL64309A0/xx unknown
- 1981-11-18 IL IL64308A patent/IL64308A/xx unknown
- 1981-11-18 US US06/322,673 patent/US4420324A/en not_active Expired - Fee Related
- 1981-11-18 US US06/322,674 patent/US4376645A/en not_active Expired - Fee Related
- 1981-11-24 CA CA000390754A patent/CA1164879A/en not_active Expired
- 1981-11-24 CA CA000390773A patent/CA1176271A/en not_active Expired
- 1981-11-26 DD DD81235151A patent/DD201091A5/de unknown
- 1981-11-26 DD DD81235152A patent/DD201750A5/de unknown
- 1981-12-03 AR AR287696A patent/AR229598A1/es active
- 1981-12-04 DK DK537281A patent/DK537281A/da not_active Application Discontinuation
- 1981-12-04 DK DK537181A patent/DK537181A/da not_active Application Discontinuation
- 1981-12-04 BR BR8107887A patent/BR8107887A/pt unknown
- 1981-12-04 AU AU78276/81A patent/AU7827681A/en not_active Abandoned
- 1981-12-04 BR BR8107888A patent/BR8107888A/pt unknown
- 1981-12-04 IE IE2850/81A patent/IE51728B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL64308A (en) | 1985-02-28 |
| AR229598A1 (es) | 1983-09-30 |
| EP0053698B1 (de) | 1985-01-09 |
| AU7827681A (en) | 1982-06-10 |
| IE51728B1 (en) | 1987-03-04 |
| DE3168194D1 (en) | 1985-02-21 |
| IL64308A0 (en) | 1982-02-28 |
| DD201091A5 (de) | 1983-07-06 |
| EP0053698A1 (de) | 1982-06-16 |
| DD201750A5 (de) | 1983-08-10 |
| DK537281A (da) | 1982-06-06 |
| CA1176271A (en) | 1984-10-16 |
| BR8107888A (pt) | 1982-09-08 |
| IE812850L (en) | 1982-06-05 |
| IL64309A0 (en) | 1982-02-28 |
| DK537181A (da) | 1982-06-06 |
| GR75122B (enEXAMPLES) | 1984-07-13 |
| US4420324A (en) | 1983-12-13 |
| DE3160972D1 (en) | 1983-10-27 |
| EP0053699B1 (de) | 1983-09-21 |
| EP0053699A1 (de) | 1982-06-16 |
| BR8107887A (pt) | 1982-09-08 |
| US4376645A (en) | 1983-03-15 |
| GR74695B (enEXAMPLES) | 1984-07-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |