JPH0153843B2 - - Google Patents
Info
- Publication number
- JPH0153843B2 JPH0153843B2 JP60287757A JP28775785A JPH0153843B2 JP H0153843 B2 JPH0153843 B2 JP H0153843B2 JP 60287757 A JP60287757 A JP 60287757A JP 28775785 A JP28775785 A JP 28775785A JP H0153843 B2 JPH0153843 B2 JP H0153843B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- acid blue
- general formula
- formula
- anion
- 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
- 239000000203 mixture Substances 0.000 claims description 35
- 230000002363 herbicidal effect Effects 0.000 claims description 19
- 150000003839 salts Chemical group 0.000 claims description 17
- 150000001450 anions Chemical class 0.000 claims description 11
- 239000004480 active ingredient Substances 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- HMEKVHWROSNWPD-UHFFFAOYSA-N Erioglaucine A Chemical compound [NH4+].[NH4+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C(=CC=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 HMEKVHWROSNWPD-UHFFFAOYSA-N 0.000 claims description 4
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 4
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical group N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 235000012745 brilliant blue FCF Nutrition 0.000 claims description 3
- 239000004161 brilliant blue FCF Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 239000006103 coloring component Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- JMXROTHPANUTOJ-UHFFFAOYSA-H naphthol green b Chemical compound [Na+].[Na+].[Na+].[Fe+3].C1=C(S([O-])(=O)=O)C=CC2=C(N=O)C([O-])=CC=C21.C1=C(S([O-])(=O)=O)C=CC2=C(N=O)C([O-])=CC=C21.C1=C(S([O-])(=O)=O)C=CC2=C(N=O)C([O-])=CC=C21 JMXROTHPANUTOJ-UHFFFAOYSA-H 0.000 claims description 3
- 125000004001 thioalkyl group Chemical group 0.000 claims description 3
- RTMBGDBBDQKNNZ-UHFFFAOYSA-L C.I. Acid Blue 3 Chemical compound [Ca+2].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=C(O)C=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1.C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=C(O)C=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 RTMBGDBBDQKNNZ-UHFFFAOYSA-L 0.000 claims description 2
- 235000012736 patent blue V Nutrition 0.000 claims description 2
- -1 salt sodium salt Chemical class 0.000 description 13
- 239000000975 dye Substances 0.000 description 9
- 239000003086 colorant Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 239000003205 fragrance Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000002895 emetic Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 208000032484 Accidental exposure to product Diseases 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 239000003905 agrochemical Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 239000005630 Diquat Substances 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- MXZACTZQSGYANA-UHFFFAOYSA-N chembl545463 Chemical compound Cl.C1=CC(OC)=CC=C1C(N=C1)=CN2C1=NC(C)=C2O MXZACTZQSGYANA-UHFFFAOYSA-N 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-O ethylaminium Chemical compound CC[NH3+] QUSNBJAOOMFDIB-UHFFFAOYSA-O 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 2
- 229950004354 phosphorylcholine Drugs 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- QBZIEGUIYWGBMY-FUZXWUMZSA-N (5Z)-5-hydroxyimino-6-oxonaphthalene-2-sulfonic acid iron Chemical compound [Fe].O\N=C1/C(=O)C=Cc2cc(ccc12)S(O)(=O)=O.O\N=C1/C(=O)C=Cc2cc(ccc12)S(O)(=O)=O.O\N=C1/C(=O)C=Cc2cc(ccc12)S(O)(=O)=O QBZIEGUIYWGBMY-FUZXWUMZSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZMESHQOXZMOOQQ-UHFFFAOYSA-N 1-(naphthalen-1-ylmethyl)naphthalene Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 ZMESHQOXZMOOQQ-UHFFFAOYSA-N 0.000 description 1
- TUHCFMAYHPGQTO-UHFFFAOYSA-M 1-ethylidene-6-pyridin-1-ium-2-yl-2H-pyridin-1-ium dibromide Chemical compound [Br-].[Br-].C(C)=[N+]1C(=CC=CC1)C1=[NH+]C=CC=C1 TUHCFMAYHPGQTO-UHFFFAOYSA-M 0.000 description 1
- IEFIPYCPABTBPE-UHFFFAOYSA-N 2-[4-(1-methylpyridin-1-ium-4-yl)pyridin-1-ium-1-yl]ethanol Chemical compound C1=C[N+](C)=CC=C1C1=CC=[N+](CCO)C=C1 IEFIPYCPABTBPE-UHFFFAOYSA-N 0.000 description 1
- DJTVSGXZSBTTIP-UHFFFAOYSA-P 2-[4-[1-(2-amino-2-oxoethyl)pyridin-1-ium-4-yl]pyridin-1-ium-1-yl]acetamide Chemical compound C1=C[N+](CC(=O)N)=CC=C1C1=CC=[N+](CC(N)=O)C=C1 DJTVSGXZSBTTIP-UHFFFAOYSA-P 0.000 description 1
- ODPOAESBSUKMHD-UHFFFAOYSA-L 6,7-dihydrodipyrido[1,2-b:1',2'-e]pyrazine-5,8-diium;dibromide Chemical compound [Br-].[Br-].C1=CC=[N+]2CC[N+]3=CC=CC=C3C2=C1 ODPOAESBSUKMHD-UHFFFAOYSA-L 0.000 description 1
- QRDZSRWEULKVNW-UHFFFAOYSA-N 6-hydroxy-2-oxo-1h-quinoline-4-carboxylic acid Chemical class C1=C(O)C=C2C(C(=O)O)=CC(=O)NC2=C1 QRDZSRWEULKVNW-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Natural products OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- CFXGQSQPCHEAAB-UHFFFAOYSA-M [Cl-].[Cl-].C(C)=[N+]1C(=CC=CC1)C1=[NH+]C=CC=C1 Chemical compound [Cl-].[Cl-].C(C)=[N+]1C(=CC=CC1)C1=[NH+]C=CC=C1 CFXGQSQPCHEAAB-UHFFFAOYSA-M 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000012872 agrochemical composition Substances 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Inorganic materials [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 description 1
- 229940006460 bromide ion Drugs 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229940005991 chloric acid Drugs 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000001046 green dye Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- 229940006461 iodide ion Drugs 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
- 239000007788 liquid Substances 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 238000012031 short term test Methods 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-I triphosphate(5-) Chemical compound [O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O UNXRWKVEANCORM-UHFFFAOYSA-I 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
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
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a Field of Industrial Application The present invention relates to a herbicidal composition containing a bipyridinium quaternary salt as a main component, and more specifically to a herbicidal composition containing a coloring component such as blue or green, whose pH is maintained under specific acidic conditions. The present invention relates to a herbicidal composition with improved stability. b. Prior Art Herbicides containing bipyridium quaternary salts as their main ingredient have a long history, and have continued to be used for more than 30 years since their invention in 1955 due to their broad herbicidal spectrum, strong effects, and stability. It's coming. That is, as with general agricultural chemicals, if sprayed according to the handling specifications, the agricultural chemical composition will not cause any harm. However, the pesticide composition is also safe for agricultural use.
Misuse, especially accidental ingestion, can in some cases have serious effects on the human body, and various measures have been taken to prevent such misuse. That is, lower aliphatic carboxylic acids as disclosed in JP-A-52-90631, or JP-A-52-90631.
One such method is to use odorants such as tetrahydrothiophene disclosed in Japanese Patent Publication No. 114021 and alkylpyridine disclosed in JP-A-49-7433 to prevent accidental ingestion and misuse due to their odor. It is one. Furthermore, various methods have been proposed for causing the swallowed substance to be vomited in the event of accidental ingestion. That is, S disclosed in Japanese Patent Application Laid-Open No. 56-35641
-Triazolopyricidine derivatives or JP-A-1986
This corresponds to the tripolyphosphate and pyrophosphate disclosed in Publication No.-61301. These preventive measures can be effective.
However, it is important as another measure to color these agricultural chemical compositions to distinguish them from other substances and to issue some kind of warning. This means that
Publication No. 35641 discloses the use of a coloring agent as a means for distinguishing or distinguishing.
However, when a coloring agent is added to an agrochemical composition, its stability becomes very important. In other words, if the color changes during storage and is misunderstood as something else, the coloring becomes meaningless, and even when added with any other substance, its excellent coloring properties and no discoloration are
This is even more important. This kind of thing is not mentioned at all in the above-mentioned Japanese Patent Application Laid-Open No. 56-35641,
Not disclosed. As a result of intensive research on the dye stability in this bipyridium salt agricultural chemical composition, the present inventors discovered the importance of the relationship between the colorant and its PH and arrived at the present invention. c. Structure of the invention That is, the present invention has the following general formula [] (However, in the formula, l represents an integer of 1 or 2, [X] l represents an anion.) and/or the following general formula [] [However, in the formula, m represents an integer of 1 or 2, [Y] n represents an anion. The two R's are the same or different alkyl groups having 1 to 5 carbon atoms, and the alkyl groups include a hydroxy group, a lower alkoxy group, a lower thioalkyl group, a lower alkylcarbonyl group, a lower alkoxycarbonyl group, a carboxy group, and a carbonylamide group. , may be substituted with a halogen group. ] A herbicidal composition containing as an active ingredient at least one dipyridinium quaternary salt represented by Acid Blue 1, Acid Blue 3,
Contains at least one coloring component selected from the group consisting of Acid Blue No. 9 and Green No. 401, and has a pH
This is a herbicidal composition maintained under acidic conditions with a pH of 5.7 or less. The dyes used in the present invention are the blue and green dyes mentioned above. This is because such pigments are not only easy to distinguish from others, but also have a warning meaning. The dye used in the present invention may be produced by any method as long as it has these colors. Specific examples of these dyes include the following. [Blue] (1) Acid Blue One (1) (CI42045.RN29â17â
9) Ethanaminium, N-(4-((4-
diethylamino)phenyl)-(2,4-
disulfophehyl)methylene)-2,5-
cyclohexadien-1-ylidene-N-ethyl-,
hydroxide inner salt sodium salt (9Cl). (2) Acid Blue Three (3) (CI42051.RN3536â
49-0) Ethanaminium, N-(4-((4-
diethylamino)phenyl)-(5-hydroxy-2,
4-disulfophenyl)methylene)-2,5-
cyclohexadien-1-ylidene)-N-ethyl-,
hydroxide inner salt calcium salt (2:1)
(9Cl). (3) Acid Blue Nine (9) (CI42090.RN2560â
18-2) Ammonium, ethyl-(4-(p-ethyl(m-
sulfob-enzyl) amino-α (o-sulfophenyl)
benzyldine)-2,5-cyclohexadien-1-
ylidene) (m-sulfob-enzyl-, hydroxide),
inner salt dimmonium salt (9Cl). (16) Green No. 401 (Naphthol Green B) Ferricâ1ânitrosoâSchaefferâ²s βâacid
salt These pigments are generally used in herbicidal compositions (aqueous solution or solid) containing bipyridium quaternary salt as an active ingredient.
10 ppm to 2% by weight, particularly preferably
A range of 100ppm to 1.0% is used. If the concentration is too low, it may be affected by various constituents and is not preferred. On the other hand, the upper limit can be used up to the solubility of the dye in the composition, and in the case of solids, it can be used at any level, but even in this case, for economic reasons, it is recommended to use up to the upper limit of solubility when it is made into a water-soluble composition. The above ranges are preferably used. The color used may be either the blue or green mentioned above. However, as colors that are naturally rare, blue is particularly preferred. However, when using dyes such as these, pH is particularly important for their stability. That is, the pH at which this product is used is preferably 5.7 or less, particularly 5.5 or less. If the pH is 6 or higher and the product is brought to neutral or substantially alkaline conditions, not only will a subtle color change occur in the colored product, but also the stability, especially long-term stability, will deteriorate, and the effect as a colored product will fade.
Color confusion is likely to occur. In other words, long-term stability is not recognized in short-term tests.
It is maintained by adjusting the pH to the above conditions. That is, in the herbicidal composition containing the above-mentioned dye containing dipyridium quaternary salt as an active ingredient, by maintaining the PH in the above range, that is, by controlling the PH to 5.7 or less, particularly 5.5 or less, the dye It is possible to obtain a herbicidal composition containing a dipyridium quaternary salt as an active ingredient, which is stable over a long period of time and is safer. There is no particular lower limit to the acidic conditions, but if the conditions are too strong, the soil quality may change during use. Therefore, the lower limit of such pH is preferably 1 or more, particularly 1.5 or more. The dipyridinium quaternary salt in the present invention will be explained below. 1 of the pyridinium quaternary salts of the present invention
One is represented by the following general formula []. (However, in the formula, l represents an integer of 1 or 2, [X] l
indicates an anion. ) Here, the anion is appropriately selected based on, for example, price. The anion is preferably one that yields a salt with appropriate water solubility. 1
Examples of anions that can be valent or multivalent include:
Acetic acid radical, benzenesulfonic acid radical, benzoic acid radical, bromate radical, bromide ion, butyric acid radical, chloric acid radical, chloride ion, citric acid radical, formic acid radical, fluorosilicic acid radical,
fumaric acid radical, fluoroboric acid radical, iodide ion,
Mention may be made of lactate, malate, maleate, methylsulfate, nitrate, propionate, phosphate, salicylate, sulfamate, succinate, sulfate, thiocyanate, tartrate and p-toluenesulfonate. . Preferred are bromide, chloride, iodide or methyl sulfate. Examples of the above general formula [] are: (a) 1,1-ethylene-2,2'-bipyridylium dibromide (diquat dibromide)
(diquat dibromide) (b) 1,1-ethylene-2,2'-bipyridinium dichloride (c) 1,1-ethylene-2,2'-bipyridinium diiodide. The method for producing such a compound is not particularly limited. For example, when diquat dibromide is used as this compound, the present invention is suitable for compounds produced by quaternizing pyridine as a raw material using 22 bipyridyl and ethylene bromide, which are double-produced using a Raney-nickel catalyst. is applicable. On the other hand, other dipyridinium salts have the following general formula []
It is expressed as [However, in the formula, m represents an integer of 1 or 2, [Y] n
indicates an anion. The two R's are the same or different alkyl groups having 1 to 5 carbon atoms, and the alkyl groups include a hydroxy group, a lower alkoxy group, a lower thioalkyl group, a lower alkylcarbonyl group,
It may be substituted with a lower alkoxycarbonyl group, a carboxy group, a carbonylamide group, or a halogen group. ] As the anion in the dipyridinium quaternary salt of the general formula [], the same anions as those explained for the general formula [] can be used. Examples of compounds of the general formula [] include (d) 1,1'-dimethyl-4,4'-bipyridinium dichloride (paraquat dichloride) (e) 1,1'-di-2-hydroxyethyl-4 ïŒ
4'-Bipyridinium dichloride (he) 1-(2-hydroxyethyl)-1'-methyl-
4,4'-bipyridinium dichloride(t) 1,1'-di-(carbamoylmethyl)-4,
4'-Bipyridinium dichloride(thi) 1,1'-bis-N,N-dimethylcarbamoylmethyl-4,4'-bipyridinium dichloride(li) 1,1'-bis-N,N'-diethylcarbamoylmethyl -4,4'-bipyridinium dichloride (l) 1,1'-diacetol-4,4'-bipyridinium dichloride (l) 1,1'-diethoxycarbonylmethyl-4,
Examples include 4'-bipyridinium dichloride (w), 1,1'-diallyl-4,4'-bipyridinium dibromide (w), and 1,1'-dimethylthio-4,4'-bipyridinium dibromide. The compound of the general formula [] can be produced, for example, by the method shown in the reaction formula below, that is, by reacting dipyridine with an alkyl halide. The active ingredient in the herbicidal composition of the present invention may contain the general formula [] or [], or a mixture of [] and [], but considering the long-term stability of the pigment, It is recommended that the active ingredient be a dipyridinium quaternary salt. That is, the effect of the present invention is significantly superior to herbicidal compositions containing [] alone or a mixture of [] and [] as active ingredients. Especially when using a mixture of [ ] and [ ],
For example, (a)-
(d), (b) - (d), (a) - (ch), (a) - (g) or (b)
â(g) is mentioned. When the herbicidal composition of the present invention is an aqueous solution, the amount of cations in the bipyridium quaternary salt ranges from 20 to
400g/, and in the case of a solid material, it is preferable that the amount is adjusted to be included when it is made into an aqueous solution with water or the like. In the present invention, in addition to the above-mentioned active ingredients and coloring compounds, additives such as emetics, odorants, and bittering agents are added to prevent accidents such as misuse, especially accidental ingestion, to make the product safer. It is also possible, and generally preferred, to formulate herbicidal compositions. In the present invention, emetics, odorants, bittering agents, and the like are not particularly limited as long as they satisfy the conditions for the method of the present invention. However, when the emetics, odorants, bittering agents, etc. are organic, alkyl-based or heterocyclic compounds, this may be a preferred mode of use. In addition to these warning substances, additives commonly used in herbicidal compositions can also be added.
That is, surfactants such as alkyl sulfates, alkyl sulfonates, lignin sulfonates, polyoxyethylene glycol ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene sorbitan monoalkylate, dinaphthylmethane disulfonate, Emulsifier or dispersant or urea agent; one or two of various auxiliary agents such as carboxymethyl cellulose, gum arabic, etc.
Prepared using more than one species. The composition of the present invention can be used as a preparation in a conventional form such as a solution, emulsion, suspension, powder, paste or granule. Such formulations include, for example, talc, bentonite,
Clay, kaolin, diatomaceous earth, white carbon,
Solid carriers such as vermiculite, slaked lime, ammonium sulfate, urea; water, alcohol, dioxane, acetone,
xylene, cyclohexane, methylnaphthalene,
Liquid carriers include dimethylformamide. Among these forms, an aqueous solution form using water is particularly preferably used. However, for certain special uses, such as gelling agents, solid substances,
Furthermore, solid forms are used in methods such as adding this to water or drinking water to gel it and prevent misuse. The present invention will be described in detail below with reference to Examples. Example 1 (Preparation of a composition containing Acid Blue 1) 355.1 g of a concentrated aqueous solution of 35.0% by weight of 1,1'-dimethyl-4,4'-bipyridylium dichloride (hereinafter abbreviated as PQã»C12) and 565.0 g of a concentrated aqueous solution of 30.0% by weight of 1,1'-ethylene-2,2'-bipyridylium dibromide (hereinafter abbreviated as DQã»Br2), and a nonionic surfactant (alkylphenyl ether ) 20.0g and polyoxyethylene alkylamine surfactant 40.0g
About 100 ml of water was added, and the pH was adjusted to 1.5 with concentrated hydrochloric acid. To this, 0.30 g of a heterocyclic emetic and 6.50 g of a 20% aqueous solution of a coloring agent (Acid Blue 1) were added, and then an odorant (amine type) was added to 8.0 g, and water was added to bring the total volume to 1.0 liters. did. The main composition of this herbicidal composition was as follows. PQã»C12 11.0% by weight DQã»Br2 15.0ã Surfactant 6.0W/V% Emetic 0.03ã Odorant 0.8ã Colorant 0.15ã PH 5.5 Example 2 (Preparation of composition containing Acid Blue-9 ) A composition with a pH of 4.0 was prepared in the same manner as in Example 1, except that Acid Blue-9 was used as the colorant. Examples 1 to 4 and Comparative Examples 1 to 4 In Example 1, herbicidal compositions with pH adjusted to various values were prepared using the pigments shown in Table 1 below.
ãè¡šããtableã
ãè¡šã
å®æœäŸ ïŒ
ïŒå®å®æ§è©ŠéšïŒ
äžèšå®æœäŸïŒãïŒããã³æ¯èŒäŸïŒãïŒã§åŸãã
ãããããã®é€èæ§çµæç©ãäžèšè¡šïŒã«ç€ºããæž©
床ããã³é°å²æ°äžã§åè¡šã«ç€ºããæéä¿æããã
ãã®çµæãæ³¢é·åžå
床ã®å€åçïŒïŒ
ïŒã§ç€ºããã
ããªãã¡çµæç©ã®250åæ°Žåžé液ã®åžå
床ãïŒcm
ç³è±ã»ã«ã§æ³¢é·750ã400nïœåã§ããããã®è²çŽ
ã®åæã®æ³¢é·ã«ãããŠæž¬å®ããŠãçµæç©ã®èª¿è£œæ
ã100ãšãããšãã®ä¿ååŸã®å¢æžçãçžå¯Ÿå€ïŒïŒ
ïŒ
ã§è¡šãããŠç€ºããã[Table] Example 5 (Stability Test) The herbicidal compositions obtained in Examples 1 to 4 and Comparative Examples 1 to 4 were tested at the temperatures and atmospheres shown in Table 2 below. Holds time.
The results were expressed as a rate of change (%) in wavelength absorbance.
In other words, the absorbance of a 250-fold diluted solution of the composition in water is 1 cm.
Relative value (%) of increase/decrease rate after storage when measured in a quartz cell in the wavelength range of 750 to 400 nm at the unique wavelength of each dye, with the time of preparation of the composition set as 100
It is expressed as
ãè¡šã
èä¹
æ§ã調ã¹ãã
[Table] Durability was investigated.
Claims (1)
ãããã¯ç°ãªãççŽ æ°ïŒãïŒã®ã¢ã«ãã«åºã§ã
ãããã®ã¢ã«ãã«åºã¯ãããããã·åºãäœçŽã¢ã«
ã³ãã·åºãäœçŽããªã¢ã«ãã«åºãäœçŽã¢ã«ãã«ã«
ã«ããã«åºãäœçŽã¢ã«ã³ãã·ã«ã«ããã«åºãã«ã«
ããã·åºãã«ã«ããã«ã¢ããåºãããã²ã³åºã§çœ®
æãããŠããããã ã§è¡šãããããžããªãžããŠã ïŒçŽå¡©ã®å°ããšãäž
çš®ãæå¹æåãšããé€èæ§çµæç©ã§ãã€ãŠã該çµ
æç©ã¯ãã¢ã·ãããã«ãŒïŒãã¢ã·ãããã«ãŒïŒã
ã¢ã·ãããã«ãŒïŒãåã³ç·è²401å·ãããªã矀ã
ãéžã°ããå°ããšãäžçš®ã®çè²æåãå«æãäžã€
PHã5.7以äžã®é žæ§æ¡ä»¶ã«ç¶æãããé€èæ§çµæ
ç©ã[Claims] 1. The following general formula [] (However, in the formula, l represents an integer of 1 or 2, [X] l represents an anion.) and/or the following general formula [] [However, in the formula, m represents an integer of 1 or 2, and [Y] n represents an anion. The two R's are the same or different alkyl groups having 1 to 5 carbon atoms, and the alkyl groups include a hydroxy group, a lower alkoxy group, a lower thioalkyl group, a lower alkylcarbonyl group, a lower alkoxycarbonyl group, a carboxy group, and a carbonylamide group. , may be substituted with a halogen group. ] A herbicidal composition containing as an active ingredient at least one dipyridinium quaternary salt represented by Acid Blue 1, Acid Blue 3,
Contains at least one coloring component selected from the group consisting of Acid Blue 9 and Green No. 401, and
A herbicidal composition maintained under acidic conditions with a pH of 5.7 or less.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP28775785A JPS62148405A (en) | 1985-12-23 | 1985-12-23 | Herbicidal composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP28775785A JPS62148405A (en) | 1985-12-23 | 1985-12-23 | Herbicidal composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62148405A JPS62148405A (en) | 1987-07-02 |
| JPH0153843B2 true JPH0153843B2 (en) | 1989-11-15 |
Family
ID=17721361
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP28775785A Granted JPS62148405A (en) | 1985-12-23 | 1985-12-23 | Herbicidal composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62148405A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2639409B2 (en) * | 1987-12-15 | 1997-08-13 | ã¢ã°ãã«ãã·ã§ãŠæ ªåŒäŒç€Ÿ | How to control grass disease |
| JP2869935B2 (en) * | 1988-03-11 | 1999-03-10 | ã«ã·ãªèšç®æ©æ ªåŒäŒç€Ÿ | Crosslinked polymer |
| AU2003902064A0 (en) * | 2003-04-30 | 2003-05-15 | Australian Agricultural Chemicals | Colouring agent for turf |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5933202A (en) * | 1982-08-20 | 1984-02-23 | Asahi Chem Ind Co Ltd | Colored composition of agricultural chemical |
-
1985
- 1985-12-23 JP JP28775785A patent/JPS62148405A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5933202A (en) * | 1982-08-20 | 1984-02-23 | Asahi Chem Ind Co Ltd | Colored composition of agricultural chemical |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62148405A (en) | 1987-07-02 |
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