JPS5817722B2 - Method for producing water-soluble pesticides - Google Patents
Method for producing water-soluble pesticidesInfo
- Publication number
- JPS5817722B2 JPS5817722B2 JP14719879A JP14719879A JPS5817722B2 JP S5817722 B2 JPS5817722 B2 JP S5817722B2 JP 14719879 A JP14719879 A JP 14719879A JP 14719879 A JP14719879 A JP 14719879A JP S5817722 B2 JPS5817722 B2 JP S5817722B2
- Authority
- JP
- Japan
- Prior art keywords
- water
- soluble
- ether
- agricultural chemical
- present
- 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
- 239000000575 pesticide Substances 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 239000000203 mixture Substances 0.000 claims description 17
- 239000004480 active ingredient Substances 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 239000003905 agrochemical Substances 0.000 claims description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 8
- 239000013078 crystal Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims description 4
- 235000019341 magnesium sulphate Nutrition 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- 239000007832 Na2SO4 Substances 0.000 claims description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 2
- 229910017053 inorganic salt Inorganic materials 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 235000017550 sodium carbonate Nutrition 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 2
- 235000011152 sodium sulphate Nutrition 0.000 claims description 2
- -1 flamethrin Chemical compound 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 238000009472 formulation Methods 0.000 description 11
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 9
- 238000004806 packaging method and process Methods 0.000 description 8
- 239000003814 drug Substances 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 239000000839 emulsion Substances 0.000 description 7
- 239000004009 herbicide Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 239000012868 active agrochemical ingredient Substances 0.000 description 4
- 239000000645 desinfectant Substances 0.000 description 4
- 239000002917 insecticide Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 230000000749 insecticidal effect Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000238657 Blattella germanica Species 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000875 corresponding effect Effects 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- ZNOLGFHPUIJIMJ-UHFFFAOYSA-N fenitrothion Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C(C)=C1 ZNOLGFHPUIJIMJ-UHFFFAOYSA-N 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 125000005702 oxyalkylene group Chemical group 0.000 description 2
- 239000005648 plant growth regulator Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- ZCVAOQKBXKSDMS-AQYZNVCMSA-N (+)-trans-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-AQYZNVCMSA-N 0.000 description 1
- SBNFWQZLDJGRLK-RTWAWAEBSA-N (1R)-trans-phenothrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 SBNFWQZLDJGRLK-RTWAWAEBSA-N 0.000 description 1
- PRPINYUDVPFIRX-UHFFFAOYSA-N 1-naphthaleneacetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-N 0.000 description 1
- CSHOPPGMNYULAD-UHFFFAOYSA-N 1-tridecoxytridecane Chemical compound CCCCCCCCCCCCCOCCCCCCCCCCCCC CSHOPPGMNYULAD-UHFFFAOYSA-N 0.000 description 1
- FMTFEIJHMMQUJI-NJAFHUGGSA-N 102130-98-3 Natural products CC=CCC1=C(C)[C@H](CC1=O)OC(=O)[C@@H]1[C@@H](C=C(C)C)C1(C)C FMTFEIJHMMQUJI-NJAFHUGGSA-N 0.000 description 1
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
- 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 1
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 1
- XJFIKRXIJXAJGH-UHFFFAOYSA-N 5-chloro-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical group ClC1=CC=C2NC(=O)NC2=N1 XJFIKRXIJXAJGH-UHFFFAOYSA-N 0.000 description 1
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- NYQDCVLCJXRDSK-UHFFFAOYSA-N Bromofos Chemical compound COP(=S)(OC)OC1=CC(Cl)=C(Br)C=C1Cl NYQDCVLCJXRDSK-UHFFFAOYSA-N 0.000 description 1
- GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 description 1
- 239000005945 Chlorpyrifos-methyl Substances 0.000 description 1
- ULSLJYXHZDTLQK-UHFFFAOYSA-N Coumatetralyl Chemical compound C1=CC=CC2=C1OC(=O)C(C1C3=CC=CC=C3CCC1)=C2O ULSLJYXHZDTLQK-UHFFFAOYSA-N 0.000 description 1
- 239000005630 Diquat Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000001293 FEMA 3089 Substances 0.000 description 1
- JHJOOSLFWRRSGU-UHFFFAOYSA-N Fenchlorphos Chemical compound COP(=S)(OC)OC1=CC(Cl)=C(Cl)C=C1Cl JHJOOSLFWRRSGU-UHFFFAOYSA-N 0.000 description 1
- PNVJTZOFSHSLTO-UHFFFAOYSA-N Fenthion Chemical compound COP(=S)(OC)OC1=CC=C(SC)C(C)=C1 PNVJTZOFSHSLTO-UHFFFAOYSA-N 0.000 description 1
- 229930191978 Gibberellin Natural products 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 239000005573 Linuron Substances 0.000 description 1
- 239000005949 Malathion Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- ISRUGXGCCGIOQO-UHFFFAOYSA-N Rhoden Chemical compound CNC(=O)OC1=CC=CC=C1OC(C)C ISRUGXGCCGIOQO-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000006011 Zinc phosphide Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 239000011717 all-trans-retinol Substances 0.000 description 1
- 235000019169 all-trans-retinol Nutrition 0.000 description 1
- 229940024113 allethrin Drugs 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000000073 carbamate insecticide Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- BIWJNBZANLAXMG-YQELWRJZSA-N chloordaan Chemical compound ClC1=C(Cl)[C@@]2(Cl)C3CC(Cl)C(Cl)C3[C@]1(Cl)C2(Cl)Cl BIWJNBZANLAXMG-YQELWRJZSA-N 0.000 description 1
- 229960003260 chlorhexidine Drugs 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007682 dermal toxicity Effects 0.000 description 1
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 1
- OEBRKCOSUFCWJD-UHFFFAOYSA-N dichlorvos Chemical compound COP(=O)(OC)OC=C(Cl)Cl OEBRKCOSUFCWJD-UHFFFAOYSA-N 0.000 description 1
- 229950001327 dichlorvos Drugs 0.000 description 1
- JXSJBGJIGXNWCI-UHFFFAOYSA-N diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- SYJFEGQWDCRVNX-UHFFFAOYSA-N diquat Chemical compound C1=CC=[N+]2CC[N+]3=CC=CC=C3C2=C1 SYJFEGQWDCRVNX-UHFFFAOYSA-N 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 150000002084 enol ethers Chemical class 0.000 description 1
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical group C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
- GRKSQRAVWODMGW-UHFFFAOYSA-N ethylphosphonic acid Chemical compound [CH2]CP(O)(O)=O GRKSQRAVWODMGW-UHFFFAOYSA-N 0.000 description 1
- 229950009006 fenclofos Drugs 0.000 description 1
- DIRFUJHNVNOBMY-UHFFFAOYSA-N fenobucarb Chemical compound CCC(C)C1=CC=CC=C1OC(=O)NC DIRFUJHNVNOBMY-UHFFFAOYSA-N 0.000 description 1
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 1
- IXORZMNAPKEEDV-UHFFFAOYSA-N gibberellic acid GA3 Natural products OC(=O)C1C2(C3)CC(=C)C3(O)CCC2C2(C=CC3O)C1C3(C)C(=O)O2 IXORZMNAPKEEDV-UHFFFAOYSA-N 0.000 description 1
- 239000003448 gibberellin Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 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 1
- 239000008233 hard water Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- RNNBHZYEKNHLKT-UHFFFAOYSA-N isopropylmethylpyrazolyl dimethylcarbamate Chemical compound CC(C)N1N=C(C)C=C1OC(=O)N(C)C RNNBHZYEKNHLKT-UHFFFAOYSA-N 0.000 description 1
- PVTHJAPFENJVNC-MHRBZPPQSA-N kasugamycin Chemical compound N[C@H]1C[C@H](NC(=N)C(O)=O)[C@@H](C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O PVTHJAPFENJVNC-MHRBZPPQSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229960000453 malathion Drugs 0.000 description 1
- AFCCDDWKHLHPDF-UHFFFAOYSA-M metam-sodium Chemical compound [Na+].CNC([S-])=S AFCCDDWKHLHPDF-UHFFFAOYSA-M 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-N methyl undecanoic acid Natural products CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 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 1
- 229960000490 permethrin Drugs 0.000 description 1
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229960003536 phenothrin Drugs 0.000 description 1
- 239000013459 phenoxy herbicide Substances 0.000 description 1
- BOTNYLSAWDQNEX-UHFFFAOYSA-N phenoxymethylbenzene Chemical compound C=1C=CC=CC=1COC1=CC=CC=C1 BOTNYLSAWDQNEX-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- IOUNQDKNJZEDEP-UHFFFAOYSA-N phosalone Chemical compound C1=C(Cl)C=C2OC(=O)N(CSP(=S)(OCC)OCC)C2=C1 IOUNQDKNJZEDEP-UHFFFAOYSA-N 0.000 description 1
- HOKBIQDJCNTWST-UHFFFAOYSA-N phosphanylidenezinc;zinc Chemical compound [Zn].[Zn]=P.[Zn]=P HOKBIQDJCNTWST-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 229940108410 resmethrin Drugs 0.000 description 1
- VEMKTZHHVJILDY-FIWHBWSRSA-N resmethrin Chemical compound CC1(C)[C@H](C=C(C)C)C1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-FIWHBWSRSA-N 0.000 description 1
- 231100000438 skin toxicity Toxicity 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- WWJZWCUNLNYYAU-UHFFFAOYSA-N temephos Chemical compound C1=CC(OP(=S)(OC)OC)=CC=C1SC1=CC=C(OP(=S)(OC)OC)C=C1 WWJZWCUNLNYYAU-UHFFFAOYSA-N 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- CXBMCYHAMVGWJQ-UHFFFAOYSA-N tetramethrin Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OCN1C(=O)C(CCCC2)=C2C1=O CXBMCYHAMVGWJQ-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229960005080 warfarin Drugs 0.000 description 1
- PJVWKTKQMONHTI-UHFFFAOYSA-N warfarin Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 PJVWKTKQMONHTI-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229940048462 zinc phosphide Drugs 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
【発明の詳細な説明】
本発明における担体は、Na2SO4・10H2010
H2O・7H20または、Na2CO3・10H20か
ら選ばれた結晶水を保有する水溶性無機塩で、その保有
する結晶水の5〜95%を熱処理等により除去した水溶
性無機塩、或いは、
Na2SO4・10H20、MgSO4・7 H20ま
たはNa2 CO3・10H20と、各々その該当する
各無水塩とを混合し、Na2SO4・10H20、Mg
SO4−7H20または、Na2CO3・10H20に
対して混合物全体の結晶水含有量を5〜95%になるよ
うに調整したものを担体として用いることを要件とする
ものである。Detailed Description of the Invention The carrier in the present invention is Na2SO4.10H2010
A water-soluble inorganic salt that has crystal water selected from H2O.7H20 or Na2CO3.10H20, from which 5 to 95% of the crystal water it possesses has been removed by heat treatment, or Na2SO4.10H20. Mix MgSO4・7H20 or Na2CO3・10H20 with their corresponding anhydrous salts to form Na2SO4・10H20, Mg
The requirement is to use SO4-7H20 or Na2CO3.10H20 in which the crystal water content of the entire mixture is adjusted to 5 to 95% as a carrier.
以後の実施例にいう結晶水の乾燥除去率は、上記担体か
らの値を示す。The dry removal rate of water of crystallization referred to in the following examples indicates the value from the above carrier.
本発明により、実施例(■〜XI)に示す如く、農薬有
効成分及び界面活性剤の性質及び添加量により担体中の
結晶水の除去率を調整する事により溶解性及び流動性に
優れた水溶性農薬が得られた。According to the present invention, as shown in Examples (■ to A sex pesticide was obtained.
加水分解を受けやすい農薬有効成分を用いる場合、本発
明により得られた製剤は、未乾燥の担体を用いた製剤に
比較して、経時安定性が優れていた(表1に示す)。When using agrochemical active ingredients that are susceptible to hydrolysis, the formulations obtained according to the present invention had superior stability over time compared to formulations using undried carriers (shown in Table 1).
又、効果の点でも本発明で得られた製剤と農薬有効成分
の本質及び分量が同一の乳剤タイプのものとを比較した
結果、速効性では同等であるが、残効性においては優れ
た結果が得られ、双安全性の而では優れていることが判
った。In addition, in terms of efficacy, a comparison between the formulation obtained by the present invention and an emulsion-type formulation with the same essence and amount of agricultural chemical active ingredients revealed that the formulation was equivalent in immediate effect, but superior in residual effect. was obtained, and it was found to be excellent in terms of dual safety.
これに対して、未乾燥のままの前記水溶性無機塩や尿素
、糖類等に代表される水溶性担体は潮解性に豊むため流
動性が悪くなりやすい。On the other hand, undried water-soluble carriers such as the water-soluble inorganic salts, urea, sugars, etc. are highly deliquescent and tend to have poor fluidity.
このため混入時に不均一が生じやす(、又、自動計量包
装する際も包装室内を特別に除湿する処置などが必要で
ある。For this reason, non-uniformity is likely to occur during mixing (also, special measures such as dehumidifying the inside of the packaging chamber are required when automatically weighing and packaging.
又、上述の塩で、該当する無水塩だけを担体とする製剤
は、自動計量包装時の流動性は良好であるが、使用に際
して水で希釈溶解するとき、凝集物を生じ、均一溶液を
得るために必要以上の時間を要し、又、噴霧機等の目づ
まりの原因ともなりやす℃・。In addition, preparations using only the corresponding anhydrous salt as a carrier have good fluidity when automatically measured and packaged, but when used by diluting and dissolving with water, they form aggregates, making it difficult to obtain a homogeneous solution. It takes more time than necessary to do this, and it also tends to cause clogging of sprayers, etc.
次に本発明における農薬有効成分は、使用時の希釈水中
で安定なエマルジョンが得えられる様な界面活性剤を混
合して用いることを要件とするも・のであるから、その
農薬有効成分は水に不溶性或は可溶性に関係なく適用で
きる。Next, the agricultural chemical active ingredient in the present invention is required to be used in combination with a surfactant that allows a stable emulsion to be obtained in dilution water when used. It can be applied regardless of whether it is insoluble or soluble.
又、農薬有効成分の配合限界量は、その製剤の流動性に
相関関係があるが、水不溶性の農薬有効成分を用℃・る
場合でも本発明による水溶性農薬は従来のものに比べ有
効成分含有量を、より高くすることが可能である。In addition, although the limit amount of agrochemical active ingredients is correlated with the fluidity of the formulation, even when water-insoluble agrochemical active ingredients are used, the water-soluble agrochemicals according to the present invention have less active ingredients than conventional ones. Higher contents are possible.
これに対して、例えば水溶性農薬有効成分の水溶液と水
溶性担体とからなる水溶性農薬の場合は農薬有効成分の
水に対する最大溶解限度量以下でしか適用できない。On the other hand, for example, in the case of a water-soluble agricultural chemical consisting of an aqueous solution of a water-soluble agricultural chemical active ingredient and a water-soluble carrier, it can only be applied at a level below the maximum solubility limit of the agricultural chemical active ingredient in water.
(例えば特開昭5l−54931)
又、既に水不溶性の農薬を有効成分とする水溶剤も市販
されてはいるが、担体が尿素及び糖類等潮解性物質であ
るため、吸湿により流動性が悪くなりやす(、そのため
農薬有効成分の含有濃度は10%(W/W)程度が限度
である。(For example, JP-A-51-54931) Also, water-based solutions containing water-insoluble pesticides as active ingredients are already commercially available, but because the carrier is deliquescent substances such as urea and sugars, they have poor fluidity due to moisture absorption. Therefore, the concentration of agricultural chemical active ingredients is limited to about 10% (W/W).
本発明による水溶性農薬&叡従来の乳剤及び水和剤等に
比べても製剤の安定性に何ら問題はな(、又、農薬有効
成分の効果も従来の製剤と同等或は同等以上の効果を示
した。There are no problems with the stability of the formulation of the water-soluble pesticides and additives of the present invention compared to conventional emulsions and wettable powders. showed that.
本発明方法による製品は、好流動性のため包装が簡便に
なり、少量(例えば3〜1007のパック形態)から多
量(例えば20〜・25kyの製形態の製形の自動包装
が可能であり、従来の液剤に使用されている容器(例え
ば、缶、瓶等)に比べて包装に要するコストは安価にな
る。The product produced by the method of the present invention can be easily packaged due to its good flowability, and can be automatically packaged in small quantities (e.g., 3-1007 packs) to large quantities (e.g., 20-25 ky). Packaging costs are lower than containers (eg, cans, bottles, etc.) used for conventional liquid medicines.
又、°本製品は有機溶剤を使用しないので環境を汚染せ
ず、しかも安全性に優れ、省資源的で、かつ石油事情に
よるコストの影響を受けにくい等の優れた大きな特長が
ある。In addition, this product does not use organic solvents, so it does not pollute the environment, and has other great features such as being highly safe, resource-saving, and not easily affected by costs due to the petroleum situation.
本発明実施に際し薬事法又は薬事法の規定に基いて厚生
大臣より医薬品又は医薬部外品としての使用を認められ
た農薬有効成分を使用した場合は医薬品又は医薬部外品
として使用し得るものである。When implementing the present invention, if an active ingredient of agrochemicals that has been approved for use as a drug or quasi-drug by the Minister of Health and Welfare based on the provisions of the Pharmaceutical Affairs Law or the Pharmaceutical Affairs Law is used, it may be used as a drug or quasi-drug. be.
本発明で単独あるいは混合で使用される農薬有効成分に
は例えば以下の様なものがあるが、必ずしもこれらに限
定されるものではない。Examples of agrochemical active ingredients that can be used alone or in combination in the present invention include, but are not necessarily limited to, the following.
殺虫剤
アレスリン・フェノトリン・フタルスリン・ペルメトリ
ン・フラメトリン・スミサイジン・レスメスリン等のピ
レスロイド系殺虫剤、カルクロホス・クロルピリホスメ
チル・シアホス・ジクロルボス・ダイアジノン・テメホ
ス・トリクロルホンナレド・ヒリダフエンチオン・フェ
ニトロチオンフェンクロホス・フェンチオン・ブロモホ
ス・マラチオン等の有機リン系殺虫剤、イソラン・カー
バム・プロポクスル・ブナポン・バッサ等のカーバメイ
ト系殺虫剤、及び、クロルデン・テトラジホン・ホサロ
ン等の殺虫剤。Insecticides Pyrethroid insecticides such as allethrin, phenothrin, phthalthrin, permethrin, flamethrin, sumicidin, resmethrin, calclophos, chlorpyrifos methyl, siafos, dichlorvos, diazinon, temephos, trichlorhonnared, hyridafention, fenitrothion, fenclofos, fenthion, Organophosphorus insecticides such as bromophos and malathion, carbamate insecticides such as isolane, carbam, propoxur, bunapon, and bassa, and insecticides such as chlordane, tetradifone, and phosalon.
殺菌剤
サーラム・ジネブ等のイオウ系殺菌剤、CPA・PCB
A−PCP等の有機塩素系殺菌剤、ダイジン・フェナジ
ン・第4アンモニウム塩・クロルヘキシジン等の窒素系
殺菌剤、キャブタン・ダイホルタン等のフタール酸系殺
菌剤、EBP等の有機リン系殺菌剤、オルトフェニルフ
ェノール等のジフェニル系殺菌剤、及び、カスガマイシ
ン・ストレプトマイシン・プラストサイジンS等の抗生
物質。Sulfur-based fungicides such as sarum and zineb, CPA and PCB
Organochlorine disinfectants such as A-PCP, nitrogen disinfectants such as daidzine, phenazine, quaternary ammonium salts, and chlorhexidine, phthalate disinfectants such as cabtane and difortan, organophosphorus disinfectants such as EBP, orthophenyl Diphenyl fungicides such as phenol, and antibiotics such as kasugamycin, streptomycin, and plasticidin S.
除草剤
DPA−TCA等の有機系除草剤、NIP・2.4−p
A−MCp等のジフェニルエーテル系及びフェノキシ系
除草剤、CAT等のトリアジン系除草剤、DCMU・リ
ニュロン等の尿素系除草剤、ペンチオカーブ等のカーバ
メート系除草剤、及び、パラコート・ジクワット等の有
機系除草剤。Organic herbicides such as herbicide DPA-TCA, NIP/2.4-p
Diphenyl ether and phenoxy herbicides such as A-MCp, triazine herbicides such as CAT, urea herbicides such as DCMU and linuron, carbamate herbicides such as penthiocarb, and organic herbicides such as paraquat and diquat. .
殺ソ剤
リン化亜鉛・ワルファリン・ツマリン・シリロシド・ア
ンツー・エンドックス・ノルポルマイト等の殺ソ剤。Sorbicidal agents such as zinc phosphide, warfarin, thumarin, silyloside, antu, endox, norpolmite.
植物生長調節剤
パラピン・ポリオキシエチレンドコサール・ポリオキシ
エチレンへキジタン脂肪酸・2−りo /L/エチルホ
スホン酸・ジベレリン・3・4−キシリル−N−メチル
カーバメイト・α−ナフタリン酢酸・N−(ジメチルア
ミノ)エフシンアミド酸・オキソエチレンナタネ油アル
コール等の植物生長調節剤。Plant growth regulator parapine, polyoxyethylene docosal, polyoxyethylene hekiditane fatty acid, 2-riO/L/ethylphosphonic acid, gibberellin, 3,4-xylyl-N-methylcarbamate, α-naphthalene acetic acid, N- Plant growth regulators such as (dimethylamino)efcinamidic acid and oxoethylene rapeseed oil alcohol.
展着剤
POEアルキルエーテル・POEアルキルアリルエーテ
ル・POEアルキルZエノールエーテル・POEへキシ
タン脂肪酸・パラフィン・POEアルキルフェニルエー
テル・POEトリデシルエーテル・アルキルアリルポリ
クリコールエーテル・アルキルフェノールポリエチルグ
リコールエーテル・テレピン油・POEアリルエーテル
スルホン酸等。Spreading agent POE alkyl ether, POE alkyl allyl ether, POE alkyl Z enol ether, POE hexitane fatty acid, paraffin, POE alkylphenyl ether, POE tridecyl ether, alkylaryl polycricol ether, alkylphenol polyethyl glycol ether, turpentine oil, POE allyl ether sulfonic acid, etc.
本発明において使用する界面活性剤を例示すれば次の通
りである。Examples of surfactants used in the present invention are as follows.
ラウリル酸アルコール硫酸エステル・アルキル(C6〜
16)ベンゼンスルホン酸塩(NaSK。Lauric acid alcohol sulfate ester/alkyl (C6~
16) Benzene sulfonate (NaSK.
Ca、Mg、Zn、、Ba等)・ポリオキシアルキレン
(C2〜4.8)モノアルキル(又はアルケニル](C
1〜24)エーテル(n=1〜150)・ポリオキシア
ルキレンモノ(又はビス、トリス、テトラキス、ペンタ
キス)ベンジルフェニルエーテル(n’= 1〜200
)・ポリオキシアルキレン(モノ−ペンタ)スチリルフ
ェニルエーテル(n=1〜200)・ポリオキシアルキ
レン(02〜4.8)モノ〔アルキル又はアルケニル(
C1〜18)フェニル〕エーテル(n−1〜150)・
ポリ(1〜200)オキシアルキレン〔モノ、ジ、トリ
アリール(ベンジル、α−メチルベンジル、クミル、フ
ェニル)フェニル〕エーテル・ホルムアルデヒド重縮合
物・ポ’J (1〜100)オキシアルキレン(02〜
4)(モノ(又はジノアルキル(アルケニル、C1〜2
4)フェニル〕エーテル・アルムアルデヒド重縮合物・
ヒマシ油脂肪酸(Na、に、Li、Ca等)塩・トール
油カリウム塩・硫酸化動植物油脂等。Ca, Mg, Zn, Ba, etc.), polyoxyalkylene (C2-4.8) monoalkyl (or alkenyl) (C
1-24) Ether (n = 1-150) / polyoxyalkylene mono (or bis, tris, tetrakis, pentakis) benzyl phenyl ether (n' = 1-200
)・Polyoxyalkylene (mono-penta)styrylphenyl ether (n=1-200)・Polyoxyalkylene (02-4.8) mono[alkyl or alkenyl (
C1-18) phenyl]ether (n-1-150)
Poly(1-200) oxyalkylene [mono, di, triaryl (benzyl, α-methylbenzyl, cumyl, phenyl) phenyl] ether/formaldehyde polycondensate/Po'J (1-100) oxyalkylene (02-
4) (mono(or dinoalkyl(alkenyl, C1-2
4) Phenyl]ether/almaldehyde polycondensate/
Castor oil fatty acid (Na, Ni, Li, Ca, etc.) salts, tall oil potassium salts, sulfated animal and vegetable oils, etc.
実施例 実施例中の分量は100′?中の重量(めを示す。Example The amount in the example is 100'? Indicates the weight of the inside.
また、実施例中の溶解性及び計量包装時の流動性につい
ては、次の様な方法で判定した。In addition, solubility in Examples and flowability during weighing and packaging were determined by the following methods.
■ 溶解性
試料5?を200mAの共せんメスシリンダーに入れ、
20°で標準5°硬水を加えて100m1lとし、2秒
間に1回の割合でメスシリンダーを30回倒立するとき
試料は完全に溶解し乳化する。■ Soluble sample 5? into a 200mA graduated cylinder,
At 20°, add standard 5° hard water to make 100 ml, and invert the graduated cylinder 30 times at a rate of once every 2 seconds until the sample is completely dissolved and emulsified.
■ 計量包装時の流動性
自動包装機で自動パック包装が容易にできるか、困難か
を容量3グ、51.10グ及び20グについて検討した
。■ Fluidity during measuring and packaging We examined whether automatic packaging was easy or difficult to perform using an automatic packaging machine for capacities of 3g, 51.10g, and 20g.
〔本例使用機種:「バイ・パッカー」型式SAM−P
101−B三元機械■社製〕
実施例 ■
◎実施例中の界面活性剤の成分は下記の通りで あ
る。[Model used in this example: “Bi-Packer” model SAM-P
101-B manufactured by Sangen Kikai ■ Co., Ltd.] Example ■ ◎ The components of the surfactant in the examples are as follows.
表1に示す通り農薬有効成分(フェニトロチオン)の経
時安定性について、本発明により得られた製剤と、未乾
燥の担体のみを用いて得られた製剤を比較した結果、本
発明により得られた製剤の安定性が優れていることが判
った。As shown in Table 1, the stability of the active agricultural ingredient (fenitrothion) over time was compared between the formulation obtained according to the present invention and the formulation obtained using only an undried carrier. It was found that the stability was excellent.
効果の比較
■、供試試料
■ 水溶性タイプ(iooy中下記成分を有する)
■ 対照薬剤(有効成分及び分量が試料■と同じもので
乳剤タイプ)
(100グ中下記成分を有する)
〔1〕 効力
(1)1紙接触法によるイエバエ成虫に対する殺虫効果
限定時間接触(1時間) 10倍希釈
液(50ml/ m″)
(2)ガラス板継続接触法によるチャバネゴキブリに対
する殺虫効果
10倍希釈度(50ml/m) ※同−面継続接朗
水溶剤の殺虫効果は、速効性(処理直後)の面では、従
来の乳剤と同等の効果を示し、残効性の面では、チャバ
ネゴキブリの継続接触で判るように、明らかに水溶剤の
方が優れていた。Comparison of effects ■, test sample ■ Water-soluble type (iooy has the following ingredients) ■ Control drug (active ingredient and amount is the same as sample ■, emulsion type) (100 grams has the following ingredients) [1] Efficacy (1) Insecticidal effect on adult house flies using the 1 paper contact method Limited time contact (1 hour) 10 times diluted solution (50ml/m'') (2) Insecticidal effect on German cockroaches using the glass plate continuous contact method 10 times diluted (50ml) /m) *Continuous contact with the same surface The insecticidal effect of the aqueous solvent is equivalent to that of conventional emulsion in terms of immediate effect (immediately after treatment), and the residual effect is ascertained by continuous contact with German cockroaches. As such, the aqueous solvent was clearly superior.
毒性の比較
■、供試試料
■ 水溶剤タイプ(100P中下記成分を有する)
■ 対照薬剤(有効成分及び分量が試料■と同じもので
乳剤タイプ)
(100グ中下記成分を有する)
急性経口及び経皮毒性試験結果
表に示す通り、水溶剤タイプの方が従来の乳剤タイプに
比較して安全性が高いことが判った。Comparison of toxicity ■, test sample ■ Water-solvent type (contains the following ingredients in 100g) ■ Control drug (emulsion type with the same active ingredient and amount as sample ■) (contains the following ingredients in 100g) Acute oral and As shown in the dermal toxicity test results table, the water-based type was found to be safer than the conventional emulsion type.
この差は、水溶剤タイプの賦形剤に使用されている硫酸
マグネシウムと、乳剤タイプの溶剤に使用されているキ
シレン及び灯油の差に起因するものと思われる。This difference is thought to be due to the difference between the magnesium sulfate used in the water-solvent type excipient and the xylene and kerosene used in the emulsion type solvent.
水溶性農薬有効成分を用〜・た場合の本発明と特開昭5
1−54931との例。The present invention and JP-A No. 5 when water-soluble pesticide active ingredients are used
Example with 1-54931.
※ 以下「分量」は全て100グ中の重量(めを示す。*All amounts below refer to weight per 100g.
また「部」は「重量部」を意味するものとする。In addition, "parts" shall mean "parts by weight."
以上に示した通り、溶解性及び計量自動包装時の流動性
を検討した結果、本発明による製剤と、特開昭51−5
4931を比較した場合本発明による方が農薬有効成分
の水に対する溶解度による限界がないためより高濃度の
製剤を得ることができた。As shown above, as a result of studying the solubility and fluidity during automatic measuring packaging, we found that the formulation according to the present invention and JP-A-51-5
4931, it was possible to obtain a formulation with higher concentration in the present invention because there is no limit due to the solubility of the agricultural chemical active ingredient in water.
Claims (1)
0または、Na2CO3・10H20から選ばれた結晶
水を保有する水溶性無機塩を熱処理等により、その保有
する結晶水の5〜95%を乾燥除去させたもの、或はN
a2SO4・10H20、MgSO4・7H20または
Na 2 COs・10H20と各々その該当する各無
水塩とを混合し、Na25o4−10H20、MgSO
4・7H20またはNa2CO3・10H20に対して
混合物全体の結晶水含有量を5〜95%になるように調
整したものを担体とし、これに農薬有効成分と適当な界
面活性剤との混合物を加え均一に混合することを特徴と
する水溶性農薬の製造方法。1 Na2SO4・10H20, MgSO4・7H2
0 or a water-soluble inorganic salt containing crystal water selected from Na2CO3.
Mix a2SO4・10H20, MgSO4・7H20 or Na 2 COs・10H20 with their corresponding anhydrous salts, and mix Na2SO4-10H20, MgSO
4.7H20 or Na2CO3.10H20, the crystal water content of the entire mixture was adjusted to 5 to 95% as a carrier, and a mixture of agricultural chemical active ingredients and a suitable surfactant was added to this and homogeneously mixed. 1. A method for producing a water-soluble agricultural chemical, which comprises mixing with a water-soluble pesticide.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP14719879A JPS5817722B2 (en) | 1979-11-13 | 1979-11-13 | Method for producing water-soluble pesticides |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP14719879A JPS5817722B2 (en) | 1979-11-13 | 1979-11-13 | Method for producing water-soluble pesticides |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5671002A JPS5671002A (en) | 1981-06-13 |
JPS5817722B2 true JPS5817722B2 (en) | 1983-04-09 |
Family
ID=15424767
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP14719879A Expired JPS5817722B2 (en) | 1979-11-13 | 1979-11-13 | Method for producing water-soluble pesticides |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS5817722B2 (en) |
-
1979
- 1979-11-13 JP JP14719879A patent/JPS5817722B2/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
JPS5671002A (en) | 1981-06-13 |
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