JPH08253401A - Production in toxicity of agricultural chemical formulation against fish - Google Patents
Production in toxicity of agricultural chemical formulation against fishInfo
- Publication number
- JPH08253401A JPH08253401A JP8025002A JP2500296A JPH08253401A JP H08253401 A JPH08253401 A JP H08253401A JP 8025002 A JP8025002 A JP 8025002A JP 2500296 A JP2500296 A JP 2500296A JP H08253401 A JPH08253401 A JP H08253401A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- parts
- branched
- linear
- alkyl group
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 50
- 238000009472 formulation Methods 0.000 title claims abstract description 26
- 231100000419 toxicity Toxicity 0.000 title claims abstract description 23
- 230000001988 toxicity Effects 0.000 title claims abstract description 23
- 239000003905 agrochemical Substances 0.000 title claims abstract description 8
- 241000251468 Actinopterygii Species 0.000 title abstract description 20
- 238000004519 manufacturing process Methods 0.000 title description 3
- -1 fatty acid ester Chemical class 0.000 claims abstract description 56
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 45
- 239000004480 active ingredient Substances 0.000 claims abstract description 34
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 34
- 150000005690 diesters Chemical class 0.000 claims abstract description 17
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 9
- 150000004996 alkyl benzenes Chemical class 0.000 claims abstract description 9
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 9
- 239000000194 fatty acid Substances 0.000 claims abstract description 9
- 229930195729 fatty acid Natural products 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims description 22
- GNPWYHFXSMINJQ-UHFFFAOYSA-N 1,2-dimethyl-3-(1-phenylethyl)benzene Chemical compound C=1C=CC(C)=C(C)C=1C(C)C1=CC=CC=C1 GNPWYHFXSMINJQ-UHFFFAOYSA-N 0.000 claims description 21
- 239000000575 pesticide Substances 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 15
- YAFOVCNAQTZDQB-UHFFFAOYSA-N octyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OCCCCCCCC)OC1=CC=CC=C1 YAFOVCNAQTZDQB-UHFFFAOYSA-N 0.000 claims description 15
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 12
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- 235000014102 seafood Nutrition 0.000 claims description 11
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 9
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 claims description 8
- 125000004965 chloroalkyl group Chemical group 0.000 claims description 7
- 125000006840 diphenylmethane group Chemical class 0.000 claims description 7
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 claims description 6
- UUGLJVMIFJNVFH-UHFFFAOYSA-N Hexyl benzoate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1 UUGLJVMIFJNVFH-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 claims description 6
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000005498 phthalate group Chemical class 0.000 claims description 6
- ZFMQKOWCDKKBIF-UHFFFAOYSA-N bis(3,5-difluorophenyl)phosphane Chemical compound FC1=CC(F)=CC(PC=2C=C(F)C=C(F)C=2)=C1 ZFMQKOWCDKKBIF-UHFFFAOYSA-N 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- YEVQZPWSVWZAOB-UHFFFAOYSA-N 2-(bromomethyl)-1-iodo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(I)C(CBr)=C1 YEVQZPWSVWZAOB-UHFFFAOYSA-N 0.000 claims description 4
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 claims description 4
- GLYJVQDYLFAUFC-UHFFFAOYSA-N butyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCCCC GLYJVQDYLFAUFC-UHFFFAOYSA-N 0.000 claims description 4
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 claims description 4
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 claims description 4
- 229960001826 dimethylphthalate Drugs 0.000 claims description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 4
- VUHMHACHBVTPMF-UHFFFAOYSA-N nonyl benzoate Chemical compound CCCCCCCCCOC(=O)C1=CC=CC=C1 VUHMHACHBVTPMF-UHFFFAOYSA-N 0.000 claims description 4
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 claims description 4
- QMMJWQMCMRUYTG-UHFFFAOYSA-N 1,2,4,5-tetrachloro-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl QMMJWQMCMRUYTG-UHFFFAOYSA-N 0.000 claims description 3
- QHTJSSMHBLGUHV-UHFFFAOYSA-N 2-methylbutan-2-ylbenzene Chemical compound CCC(C)(C)C1=CC=CC=C1 QHTJSSMHBLGUHV-UHFFFAOYSA-N 0.000 claims description 3
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 claims description 3
- XTJFFFGAUHQWII-UHFFFAOYSA-N Dibutyl adipate Chemical compound CCCCOC(=O)CCCCC(=O)OCCCC XTJFFFGAUHQWII-UHFFFAOYSA-N 0.000 claims description 3
- YUXIBTJKHLUKBD-UHFFFAOYSA-N Dibutyl succinate Chemical compound CCCCOC(=O)CCC(=O)OCCCC YUXIBTJKHLUKBD-UHFFFAOYSA-N 0.000 claims description 3
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 claims description 3
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 claims description 3
- 229940100539 dibutyl adipate Drugs 0.000 claims description 3
- 229960002097 dibutylsuccinate Drugs 0.000 claims description 3
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 claims description 3
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 claims description 3
- HQUQLFOMPYWACS-UHFFFAOYSA-N tris(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCCCl HQUQLFOMPYWACS-UHFFFAOYSA-N 0.000 claims description 3
- LGXAANYJEHLUEM-UHFFFAOYSA-N 1,2,3-tri(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1C(C)C LGXAANYJEHLUEM-UHFFFAOYSA-N 0.000 claims description 2
- IQKPRDMUYVQFBP-UHFFFAOYSA-N 1,2-bis(2-methylbutan-2-yl)benzene Chemical compound CCC(C)(C)C1=CC=CC=C1C(C)(C)CC IQKPRDMUYVQFBP-UHFFFAOYSA-N 0.000 claims description 2
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 claims description 2
- WJECKFZULSWXPN-UHFFFAOYSA-N 1,2-didodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1CCCCCCCCCCCC WJECKFZULSWXPN-UHFFFAOYSA-N 0.000 claims description 2
- RBVSYZMOTRAELI-UHFFFAOYSA-N 1,2-dimethyl-3-(1-phenylpropyl)benzene Chemical compound C=1C=CC(C)=C(C)C=1C(CC)C1=CC=CC=C1 RBVSYZMOTRAELI-UHFFFAOYSA-N 0.000 claims description 2
- FQYVVSNFPLKMNU-UHFFFAOYSA-N 1,2-dipentylbenzene Chemical compound CCCCCC1=CC=CC=C1CCCCC FQYVVSNFPLKMNU-UHFFFAOYSA-N 0.000 claims description 2
- SZURZHQMGVKJLV-UHFFFAOYSA-N 1,2-ditert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1C(C)(C)C SZURZHQMGVKJLV-UHFFFAOYSA-N 0.000 claims description 2
- FUZLRTGGPPIBJQ-UHFFFAOYSA-N 2-n,2-n,4-n,4-n-tetramethylpyrimidine-2,4-diamine Chemical compound CN(C)C1=CC=NC(N(C)C)=N1 FUZLRTGGPPIBJQ-UHFFFAOYSA-N 0.000 claims description 2
- SVGGKWILBMPIJV-UTJQPWESSA-N butyl (9z,12z)-octadeca-9,12-dienoate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCCCC SVGGKWILBMPIJV-UTJQPWESSA-N 0.000 claims description 2
- DIBUFQMCUZYQKN-UHFFFAOYSA-N butyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OCCCC)OC1=CC=CC=C1 DIBUFQMCUZYQKN-UHFFFAOYSA-N 0.000 claims description 2
- ISXDVFNOXYQPIA-UHFFFAOYSA-N dibutyl pentanedioate Chemical compound CCCCOC(=O)CCCC(=O)OCCCC ISXDVFNOXYQPIA-UHFFFAOYSA-N 0.000 claims description 2
- OUWSNHWQZPEFEX-UHFFFAOYSA-N diethyl glutarate Chemical compound CCOC(=O)CCCC(=O)OCC OUWSNHWQZPEFEX-UHFFFAOYSA-N 0.000 claims description 2
- KWABLUYIOFEZOY-UHFFFAOYSA-N dioctyl butanedioate Chemical compound CCCCCCCCOC(=O)CCC(=O)OCCCCCCCC KWABLUYIOFEZOY-UHFFFAOYSA-N 0.000 claims description 2
- RXJJVYBGRFLCOX-UHFFFAOYSA-N dioctyl pentanedioate Chemical compound CCCCCCCCOC(=O)CCCC(=O)OCCCCCCCC RXJJVYBGRFLCOX-UHFFFAOYSA-N 0.000 claims description 2
- JYCRKSLWSLBYLT-UHFFFAOYSA-N dipentyl butanedioate Chemical compound CCCCCOC(=O)CCC(=O)OCCCCC JYCRKSLWSLBYLT-UHFFFAOYSA-N 0.000 claims description 2
- UPPJFVSCGFPFHM-UHFFFAOYSA-N dipentyl hexanedioate Chemical compound CCCCCOC(=O)CCCCC(=O)OCCCCC UPPJFVSCGFPFHM-UHFFFAOYSA-N 0.000 claims description 2
- MSICJOVDFUZPDG-UHFFFAOYSA-N dipentyl pentanedioate Chemical compound CCCCCOC(=O)CCCC(=O)OCCCCC MSICJOVDFUZPDG-UHFFFAOYSA-N 0.000 claims description 2
- IOVYZELOJXWQKD-UHFFFAOYSA-N hexyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCCCCCC IOVYZELOJXWQKD-UHFFFAOYSA-N 0.000 claims description 2
- SMWDEDPRQFUXNH-UHFFFAOYSA-N hexyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCCCC SMWDEDPRQFUXNH-UHFFFAOYSA-N 0.000 claims description 2
- 229940095102 methyl benzoate Drugs 0.000 claims description 2
- WIBFFTLQMKKBLZ-SEYXRHQNSA-N n-butyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCCC WIBFFTLQMKKBLZ-SEYXRHQNSA-N 0.000 claims description 2
- VECVSKFWRQYTAL-UHFFFAOYSA-N octyl benzoate Chemical compound CCCCCCCCOC(=O)C1=CC=CC=C1 VECVSKFWRQYTAL-UHFFFAOYSA-N 0.000 claims description 2
- VXNSQGRKHCZUSU-UHFFFAOYSA-N octylbenzene Chemical compound [CH2]CCCCCCCC1=CC=CC=C1 VXNSQGRKHCZUSU-UHFFFAOYSA-N 0.000 claims description 2
- QKNZNUNCDJZTCH-UHFFFAOYSA-N pentyl benzoate Chemical compound CCCCCOC(=O)C1=CC=CC=C1 QKNZNUNCDJZTCH-UHFFFAOYSA-N 0.000 claims description 2
- PQWBDPUBNMEITD-UHFFFAOYSA-N pentyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCCCC PQWBDPUBNMEITD-UHFFFAOYSA-N 0.000 claims description 2
- YGDMPMKCHSXJJF-UHFFFAOYSA-N pentyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCCCCC YGDMPMKCHSXJJF-UHFFFAOYSA-N 0.000 claims description 2
- MOQRZWSWPNIGMP-UHFFFAOYSA-N pentyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCCC MOQRZWSWPNIGMP-UHFFFAOYSA-N 0.000 claims description 2
- QPXYWTUZRZEUAK-UHFFFAOYSA-N pentyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OCCCCC QPXYWTUZRZEUAK-UHFFFAOYSA-N 0.000 claims description 2
- QJAVUVZBMMXBRO-UHFFFAOYSA-N tripentyl phosphate Chemical compound CCCCCOP(=O)(OCCCCC)OCCCCC QJAVUVZBMMXBRO-UHFFFAOYSA-N 0.000 claims description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims 1
- 239000005642 Oleic acid Substances 0.000 claims 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical class C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 claims 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims 1
- 230000000749 insecticidal effect Effects 0.000 abstract description 9
- 235000015170 shellfish Nutrition 0.000 abstract description 8
- 229910019142 PO4 Inorganic materials 0.000 abstract description 2
- 239000010452 phosphate Substances 0.000 abstract description 2
- 230000000845 anti-microbial effect Effects 0.000 abstract 1
- 230000002363 herbicidal effect Effects 0.000 abstract 1
- 239000004615 ingredient Substances 0.000 abstract 1
- 239000008187 granular material Substances 0.000 description 79
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 229920013632 Ryton Polymers 0.000 description 23
- 239000004736 Ryton® Substances 0.000 description 23
- 239000004927 clay Substances 0.000 description 22
- 239000000126 substance Substances 0.000 description 21
- 239000002917 insecticide Substances 0.000 description 16
- 239000004372 Polyvinyl alcohol Substances 0.000 description 15
- 229920002451 polyvinyl alcohol Polymers 0.000 description 15
- 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 14
- 229910052622 kaolinite Inorganic materials 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 235000013339 cereals Nutrition 0.000 description 10
- 238000001035 drying Methods 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 description 10
- 238000005192 partition Methods 0.000 description 9
- 231100000820 toxicity test Toxicity 0.000 description 9
- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- YREQHYQNNWYQCJ-UHFFFAOYSA-N etofenprox Chemical compound C1=CC(OCC)=CC=C1C(C)(C)COCC1=CC=CC(OC=2C=CC=CC=2)=C1 YREQHYQNNWYQCJ-UHFFFAOYSA-N 0.000 description 8
- 239000000454 talc Substances 0.000 description 8
- 229910052623 talc Inorganic materials 0.000 description 8
- 239000005896 Etofenprox Substances 0.000 description 6
- VQXSOUPNOZTNAI-UHFFFAOYSA-N Pyrethrin I Natural products CC(=CC1CC1C(=O)OC2CC(=O)C(=C2C)CC=C/C=C)C VQXSOUPNOZTNAI-UHFFFAOYSA-N 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 238000009826 distribution Methods 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 229950005085 etofenprox Drugs 0.000 description 6
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- 229920000881 Modified starch Polymers 0.000 description 5
- 239000000417 fungicide Substances 0.000 description 5
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 230000000361 pesticidal effect Effects 0.000 description 5
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- IRUJZVNXZWPBMU-UHFFFAOYSA-N cartap Chemical compound NC(=O)SCC(N(C)C)CSC(N)=O IRUJZVNXZWPBMU-UHFFFAOYSA-N 0.000 description 4
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 4
- ZNOLGFHPUIJIMJ-UHFFFAOYSA-N fenitrothion Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C(C)=C1 ZNOLGFHPUIJIMJ-UHFFFAOYSA-N 0.000 description 4
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 3
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- 240000004429 Tephrosia purpurea Species 0.000 description 3
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- 241000607479 Yersinia pestis Species 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- 239000000073 carbamate insecticide Substances 0.000 description 3
- JLQUFIHWVLZVTJ-UHFFFAOYSA-N carbosulfan Chemical compound CCCCN(CCCC)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 JLQUFIHWVLZVTJ-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- XAMUDJHXFNRLCY-UHFFFAOYSA-N phenthoate Chemical compound CCOC(=O)C(SP(=S)(OC)OC)C1=CC=CC=C1 XAMUDJHXFNRLCY-UHFFFAOYSA-N 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- QHGVXILFMXYDRS-UHFFFAOYSA-N pyraclofos Chemical compound C1=C(OP(=O)(OCC)SCCC)C=NN1C1=CC=C(Cl)C=C1 QHGVXILFMXYDRS-UHFFFAOYSA-N 0.000 description 3
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- 241000287531 Psittacidae Species 0.000 description 2
- 239000003899 bactericide agent Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- JHRWWRDRBPCWTF-OLQVQODUSA-N captafol Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)[C@H]21 JHRWWRDRBPCWTF-OLQVQODUSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- DIRFUJHNVNOBMY-UHFFFAOYSA-N fenobucarb Chemical compound CCC(C)C1=CC=CC=C1OC(=O)NC DIRFUJHNVNOBMY-UHFFFAOYSA-N 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- YEUKJHYLBPPSQJ-SEYXRHQNSA-N pentyl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCCCC YEUKJHYLBPPSQJ-SEYXRHQNSA-N 0.000 description 2
- 229910052573 porcelain Inorganic materials 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- 238000009333 weeding 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
- YOSCIBHNIINXGQ-UHFFFAOYSA-N (2,2-dimethyl-3H-1-benzofuran-7-yl) N-methylcarbamate Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2.CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 YOSCIBHNIINXGQ-UHFFFAOYSA-N 0.000 description 1
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 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
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- OWZPCEFYPSAJFR-UHFFFAOYSA-N 2-(butan-2-yl)-4,6-dinitrophenol Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O OWZPCEFYPSAJFR-UHFFFAOYSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 239000005745 Captan Substances 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- 241000252185 Cobitidae Species 0.000 description 1
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- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
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- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- XVEFAFPICKTHBB-UHFFFAOYSA-N N[SH3] Chemical compound N[SH3] XVEFAFPICKTHBB-UHFFFAOYSA-N 0.000 description 1
- LVKTWOXHRYGDMM-UHFFFAOYSA-N Naproanilide Chemical compound C=1C=C2C=CC=CC2=CC=1OC(C)C(=O)NC1=CC=CC=C1 LVKTWOXHRYGDMM-UHFFFAOYSA-N 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- UNLYSVIDNRIVFJ-UHFFFAOYSA-N Piperophos Chemical compound CCCOP(=S)(OCCC)SCC(=O)N1CCCCC1C UNLYSVIDNRIVFJ-UHFFFAOYSA-N 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- VMORCWYWLVLMDG-YZGWKJHDSA-N Pyrethrin-II Natural products CC(=O)OC(=C[C@@H]1[C@H](C(=O)O[C@H]2CC(=O)C(=C2C)CC=CC=C)C1(C)C)C VMORCWYWLVLMDG-YZGWKJHDSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 240000004460 Tanacetum coccineum Species 0.000 description 1
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- ROVGZAWFACYCSP-MQBLHHJJSA-N [2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-MQBLHHJJSA-N 0.000 description 1
- 229940024113 allethrin Drugs 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- IMHBYKMAHXWHRP-UHFFFAOYSA-N anilazine Chemical compound ClC1=CC=CC=C1NC1=NC(Cl)=NC(Cl)=N1 IMHBYKMAHXWHRP-UHFFFAOYSA-N 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- FYZBOYWSHKHDMT-UHFFFAOYSA-N benfuracarb Chemical compound CCOC(=O)CCN(C(C)C)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 FYZBOYWSHKHDMT-UHFFFAOYSA-N 0.000 description 1
- YFXPPSKYMBTNAV-UHFFFAOYSA-N bensultap Chemical compound C=1C=CC=CC=1S(=O)(=O)SCC(N(C)C)CSS(=O)(=O)C1=CC=CC=C1 YFXPPSKYMBTNAV-UHFFFAOYSA-N 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- 235000012216 bentonite Nutrition 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- LDVVMCZRFWMZSG-UHFFFAOYSA-N captan Chemical compound C1C=CCC2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C21 LDVVMCZRFWMZSG-UHFFFAOYSA-N 0.000 description 1
- 229940117949 captan Drugs 0.000 description 1
- 229960005286 carbaryl Drugs 0.000 description 1
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- XQUXKZZNEFRCAW-UHFFFAOYSA-N fenpropathrin Chemical compound CC1(C)C(C)(C)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 XQUXKZZNEFRCAW-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- HAWJXYBZNNRMNO-UHFFFAOYSA-N furathiocarb Chemical compound CCCCOC(=O)N(C)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 HAWJXYBZNNRMNO-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- QBSJMKIUCUGGNG-UHFFFAOYSA-N isoprocarb Chemical compound CNC(=O)OC1=CC=CC=C1C(C)C QBSJMKIUCUGGNG-UHFFFAOYSA-N 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 125000005645 linoleyl group Chemical group 0.000 description 1
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical compound CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 description 1
- VOEYXMAFNDNNED-UHFFFAOYSA-N metolcarb Chemical compound CNC(=O)OC1=CC=CC(C)=C1 VOEYXMAFNDNNED-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229940093429 polyethylene glycol 6000 Drugs 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- ROVGZAWFACYCSP-VUMXUWRFSA-N pyrethrin I Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-VUMXUWRFSA-N 0.000 description 1
- 229940015367 pyrethrum Drugs 0.000 description 1
- XRJLAOUDSILTFT-UHFFFAOYSA-N pyroquilon Chemical compound O=C1CCC2=CC=CC3=C2N1CC3 XRJLAOUDSILTFT-UHFFFAOYSA-N 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229940108410 resmethrin Drugs 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000006000 trichloroethyl group Chemical group 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、親油性農薬活性成
分を含有する農薬製剤の魚介類に対する毒性を軽減する
方法に関する。TECHNICAL FIELD The present invention relates to a method for reducing the toxicity of a pesticide formulation containing a lipophilic pesticide active ingredient to fish and shellfish.
【０００２】[0002]
【従来の技術】近年、殺虫・殺菌・除草などの農薬活性
を有する化合物が多数開発され、優れた効果を発揮して
いるものが少なくない。しかしながら、これらの多くは
魚介類に対する毒性が強いため水田で使用することがで
きず、果樹・そ菜などに適用するにとどまっている。そ
こで、これらの農薬を水田で使用できないという欠点を
克服する努力が続けられてきた。魚介類に対する毒性を
軽減する方法としては、従来から農薬活性成分の水中
への溶出をコントロールする方法および毒性を軽減す
る薬剤を添加する方法が考えられてきた。について
は、たとえば、チオールカルバメート系除草剤の魚毒性
を軽減する方法（特開昭５９−１６７５０７号）が知ら
れているにすぎず、農薬全般にわたって適用しうる魚毒
性軽減剤はいまだに見いだされていない。一方、につ
いては効果の持続も期待されることから、多くの研究が
行われている。たとえば、活性成分に活性炭と植物性油
とを配合したもの（特開昭５６−１６９６０１号），活
性成分に石油系樹脂と界面活性剤とを混合したもの（特
開昭５０−６７２５号），凹部を有する粒状物に活性成
分を吸着させたもの（特開昭５８−２３３６１号）など
が知られているが、いずれも効果が一定しないかまたは
効果が充分でない。2. Description of the Related Art In recent years, a large number of compounds having agrochemical activity such as insecticidal, bactericidal and weeding have been developed, and many of them exhibit excellent effects. However, many of them cannot be used in paddy fields because they are highly toxic to seafood, and are only applied to fruit trees and vegetables. Therefore, efforts have been continued to overcome the drawback that these pesticides cannot be used in paddy fields. As methods for reducing toxicity to fish and shellfish, methods for controlling elution of pesticide active ingredients into water and methods for adding a drug for reducing toxicity have been conventionally considered. For example, only a method for reducing the fish toxicity of thiol carbamate herbicides (Japanese Patent Laid-Open No. 59-167507) is known, and a fish toxicity reducing agent applicable to all pesticides is still found. Absent. On the other hand, since it is expected that the effect will be sustained, many studies have been conducted. For example, a mixture of an active ingredient with activated carbon and vegetable oil (JP-A-56-169601), a mixture of an active ingredient with a petroleum resin and a surfactant (JP-A-50-6725), There are known granules having concave portions to which an active ingredient is adsorbed (Japanese Patent Laid-Open No. 58-23361), but the effects are not constant or the effects are not sufficient.
【０００３】[0003]
【発明が解決しようとする課題】本発明者らは、広く親
油性農薬活性成分一般に適用しうる魚介類に対する毒性
を軽減する方法について鋭意研究を行った結果、親油性
農薬活性成分にある種の有機化合物を加えることにより
当該農薬の魚介類に対する毒性を顕著に抑制することが
できることを知見し、さらに研究を進めて本発明を完成
した。DISCLOSURE OF INVENTION Problems to be Solved by the Invention The inventors of the present invention have conducted diligent research on a method of reducing toxicity to seafood which can be widely applied to lipophilic pesticide active ingredients in general. It was found that the toxicity of the pesticide to fish and shellfish can be remarkably suppressed by adding an organic compound, and further research was conducted to complete the present invention.
【０００４】[0004]
【課題を解決するための手段】本発明は、（１）親油性
農薬活性成分〔Ｉ〕と、 式Ｒ1ＣＯＯＲ2 〔式中、Ｒ1は直鎖状または分枝状のＣ8-24アルキル基
またはＣ8-24アルケニル基を、Ｒ2は直鎖状または分枝
状のＣ2-12アルキル基を示す〕で表される脂肪酸エステ
ル類〔III〕、 式The present invention comprises (1) a lipophilic pesticide active ingredient [I] and a formula R 1 COOR 2 [wherein R 1 is a linear or branched C 8-24 An alkyl group or a C 8-24 alkenyl group, and R 2 represents a linear or branched C 2-12 alkyl group], a fatty acid ester [III] represented by the formula:
【化１３】 〔式中、Ｒ3は直鎖状または分枝状のＣ2-12アルキル基
を、ｍは２〜４の整数を示す〕で表されるジエステル類
〔IV〕、 式[Chemical 13] [Wherein R 3 represents a linear or branched C 2-12 alkyl group, and m represents an integer of 2 to 4], and a diester [IV] represented by the formula:
【化１４】 〔式中、Ｒ4，Ｒ5，Ｒ6は同一または異なって直鎖状ま
たは分枝状のＣ3-12アルキル基，Ｃ1-4塩化アルキル基
またはフェニル基を示す〕で表されるリン酸エステル類
〔Ｖ〕、Embedded image [Wherein R 4 , R 5 and R 6 are the same or different and each represents a linear or branched C 3-12 alkyl group, C 1-4 chloroalkyl group or phenyl group] Acid esters [V],
【０００５】式Expression
【化１５】 〔式中、Ｒ7は直鎖状または分枝状のＣ2-16アルキル
基，ｎはＲ7基が１〜４個置換していることを示す〕で
表されるアルキルベンゼン類〔VI〕、 式[Chemical 15] [Wherein, R 7 represents a linear or branched C 2-16 alkyl group, and n represents that 1 to 4 R 7 groups are substituted], an alkylbenzene compound [VI], formula
【化１６】 〔式中、Ｒ8，Ｒ9，Ｒ10は水素原子または直鎖状もしく
は分枝状のＣ1-3アルキル基を、ｐ，ｑはＲ8，Ｒ9基が
１〜３個置換していることを示す〕で表されるジフェニ
ルメタン類〔VII〕、Embedded image [In the formula, R 8 , R 9 and R 10 are hydrogen atoms or linear or branched C 1-3 alkyl groups, and p and q are substituted by 1 to 3 R 8 and R 9 groups. The diphenylmethanes [VII],
【０００６】式Expression
【化１７】 〔式中、Ｒ11は直鎖状または分枝状のＣ1-12アルキル基
を示す〕で表される安息香酸エステル類〔VIII〕および 式[Chemical 17] [In the formula, R 11 represents a linear or branched C 1-12 alkyl group], and a benzoic acid ester [VIII] and a formula
【化１８】 〔式中、Ｒ12，Ｒ13はそれぞれ直鎖状または分枝状のＣ
1-12アルキル基を示す〕で表されるフタル酸エステル類
〔IX〕から成る群から選ばれる一種または二種以上の有
機化合物〔II〕とを含有せしめることを特徴とする該農
薬活性成分を含有する農薬製剤の魚介類に対する毒性を
軽減する方法、およびEmbedded image [In the formula, R 12 and R 13 are each linear or branched C
1-12 represents an alkyl group], and one or more kinds of organic compounds [II] selected from the group consisting of phthalates [IX] represented by Method for reducing toxicity of contained pesticide formulation to seafood, and
【０００７】（９）親油性農薬活性成分〔Ｉ〕と、 式Ｒ1ＣＯＯＲ2 〔式中、Ｒ1は直鎖状または分枝状のＣ8-24アルキル基
またはＣ8-24アルケニル基を、Ｒ2は直鎖状または分枝
状のＣ2-12アルキル基を示す〕で表される脂肪酸エステ
ル類〔III〕、 式(9) A lipophilic pesticide active ingredient [I] and a compound of the formula R 1 COOR 2 [wherein R 1 represents a linear or branched C 8-24 alkyl group or a C 8-24 alkenyl group] , R 2 represents a linear or branched C 2-12 alkyl group], a fatty acid ester [III] represented by the formula:
【化１９】 〔式中、Ｒ3は直鎖状または分枝状のＣ2-12アルキル基
を、ｍは２〜４の整数を示す〕で表されるジエステル類
〔IV〕、 式[Chemical 19] [Wherein R 3 represents a linear or branched C 2-12 alkyl group, and m represents an integer of 2 to 4], and a diester [IV] represented by the formula:
【化２０】 〔式中、Ｒ4，Ｒ5，Ｒ6は同一または異なって直鎖状ま
たは分枝状のＣ3-12アルキル基，Ｃ1-4塩化アルキル基
またはフェニル基を示す〕で表されるリン酸エステル類
〔Ｖ〕、Embedded image [Wherein R 4 , R 5 and R 6 are the same or different and each represents a linear or branched C 3-12 alkyl group, C 1-4 chloroalkyl group or phenyl group] Acid esters [V],
【０００８】式Expression
【化２１】 〔式中、Ｒ7は直鎖状または分枝状のＣ2-16アルキル
基，ｎはＲ7基が１〜４個置換していることを示す〕で
表されるアルキルベンゼン類〔VI〕、 式[Chemical 21] [Wherein, R 7 represents a linear or branched C 2-16 alkyl group, and n represents that 1 to 4 R 7 groups are substituted], an alkylbenzene compound [VI], formula
【化２２】 〔式中、Ｒ8，Ｒ9，Ｒ10は水素原子または直鎖状もしく
は分枝状のＣ1-3アルキル基を、ｐ，ｑはＲ8，Ｒ9基が
１〜３個置換していることを示す〕で表されるジフェニ
ルメタン類〔VII〕、[Chemical formula 22] [In the formula, R 8 , R 9 and R 10 are hydrogen atoms or linear or branched C 1-3 alkyl groups, and p and q are substituted by 1 to 3 R 8 and R 9 groups. The diphenylmethanes [VII],
【０００９】式Expression
【化２３】 〔式中、Ｒ11は直鎖状または分枝状のＣ1-12アルキル基
を示す〕で表される安息香酸エステル類〔VIII〕および 式[Chemical formula 23] [In the formula, R 11 represents a linear or branched C 1-12 alkyl group], and a benzoic acid ester [VIII] and a formula
【化２４】 〔式中、Ｒ12，Ｒ13はそれぞれ直鎖状または分枝状のＣ
1-12アルキル基を示す〕で表されるフタル酸エステル類
〔IX〕から成る群から選ばれる一種または二種以上の有
機化合物〔II〕とを用いることを特徴とする該農薬活性
成分〔Ｉ〕の魚介類に対する毒性を軽減する方法に関す
るものである。[Chemical formula 24] [In the formula, R 12 and R 13 are each linear or branched C
1-12 alkyl group] and one or more organic compounds [II] selected from the group consisting of phthalates [IX]. ] To reduce the toxicity to seafood.
【００１０】本発明において親油性農薬活性成分とは、
殺虫，殺菌，除草などの農薬活性を有しかつ親油性であ
る化合物をいう。ここで親油性とは水に難溶もしくは不
溶であることを示す。このような化合物が魚介類に対し
て毒性を示し、かかる毒性を軽減させる必要のある場合
はすべて本発明の技術を適用することができる。このよ
うな化合物〔Ｉ〕としては、次のようなものが挙げられ
る。すなわち、親油性の殺虫剤としては、たとえばカル
ボフラン系殺虫剤，ピレスロイド系殺虫剤，カルバメー
ト系殺虫剤，親油性の有機リン系殺虫剤などが挙げられ
る。親油性の殺菌剤としては、たとえばキャプタン〔Ｎ
−（トリクロロメチルチオ）−４−シクロヘキセン−
１,２−ジカルボキシイミド，シェブロン社（Chevron C
hemical Co.）〕，カプタホル〔Ｎ−（１,１,２,２−テ
トラクロロエチルチオ）−４−シクロヘキセン−１,２
−ジカルボキシイミド、シェブロン社〕，アニラジン
〔２,４−ジクロロ−６−（ｏ−クロロアニリノ）−１,
３,５−トリアジン，ケマグロ社（Chemagro Agricultur
al Chemicals Div.）〕，ＴＰＮ〔ダコニール，テトラ
クロロイソフタロニトリル，ダイヤモンドアルカリ社
（Diamond Alkali Co.）〕などが挙げられる。親油性の
除草剤としては、たとえばアイオキシニルール〔４−シ
アノ−２,６−ジヨードフェニル オクタノエート，メ
イ・アンド・ベイカー社（May ＆ Baker, Ltd.）〕，Ｄ
ＮＢＰ〔２−sec−ブチル−４,６−ジニトロフェノー
ル，ヘキスト社（Farbwerke Hoechst AG）〕，ナプロア
ニリド〔２−（β−ナフチルオキシ）プロピオンアミ
ド，三井東圧〕，ピペロホス〔Ｓ−（２−メチルピペリ
ジノカルボニルメチル）ジプロピル ホスホロチオロチ
オネート，チバ・ガイギー社（Ciba-Geigy）〕などが挙
げられる。これらのうちカルボフラン系殺虫剤，ピレス
ロイド系殺虫剤などが本発明において特に繁用されるも
のである。In the present invention, the lipophilic pesticide active ingredient is
Compounds that have pesticidal activity such as insecticidal, bactericidal and weeding and are lipophilic. Here, lipophilic means that it is sparingly soluble or insoluble in water. When such a compound is toxic to fish and shellfish and it is necessary to reduce such toxicity, the technique of the present invention can be applied. Examples of the compound [I] include the following. That is, examples of the lipophilic insecticide include carbofuran insecticides, pyrethroid insecticides, carbamate insecticides, lipophilic organophosphorus insecticides and the like. Examples of lipophilic fungicides include captan [N
-(Trichloromethylthio) -4-cyclohexene-
1,2-Dicarboximide, Chevron C
hemical Co.)], captafol [N- (1,1,2,2-tetrachloroethylthio) -4-cyclohexene-1,2
-Dicarboximide, Chevron Co., anilazine [2,4-dichloro-6- (o-chloroanilino) -1,
3,5-triazine, Chemagro Agricultur
Al Chemicals Div.)], TPN [Daconyl, tetrachloroisophthalonitrile, Diamond Alkali Co.] and the like. As lipophilic herbicides, for example, ioxynirule [4-cyano-2,6-diiodophenyl octanoate, May & Baker, Ltd.], D
NBP [2-sec-butyl-4,6-dinitrophenol, Hoechst AG], naproanilide [2- (β-naphthyloxy) propionamide, Mitsui Toatsu], piperophos [S- (2-methyl Piperidinocarbonylmethyl) dipropyl phosphorothiolothionate, Ciba-Geigy] and the like. Of these, carbofuran insecticides, pyrethroid insecticides and the like are particularly frequently used in the present invention.
【００１１】カルボフラン系殺虫剤としては、たとえ
ば、フラチオカルブ〔ブチル ２,３−ジヒドロ−２,２
−ジメチルベンゾフラン−７−イル Ｎ,Ｎ'−ジメチル
−Ｎ,Ｎ'−チオジカルバメート，チバ・ガイギー社〕，
カルボフラン〔２,３−ジヒドロ−２,２−ジメチルベン
ゾフラン−７−イル Ｎ−メチルカルバメート，エフ・
エム・シー社（FMC Corp.），バイエル社（Bayer A
G）〕，カルボスルファン〔アドバンテージ，２,３−ジ
ヒドロ−２,２−ジメチルベンゾフラン−７−イルＮ−
（ジブチルアミノチオ）−Ｎ−メチルカルバメート，エ
フ・エム・シー社〕，アミノスルフラン〔オンコル，ア
ミノフラカルブ，エチル Ｎ−〔Ｎ'−（２,３−ジヒド
ロ−２,２−ジメチルベンゾフラン−７−イルオキシカ
ルボニル）−Ｎ'−メチルアミノチオ〕−Ｎ−イソプロ
ピル β−アラニネート，大塚製薬〕などが例示され
る。ピレスロイド系殺虫剤としては、たとえば、アレス
リン〔（±）−３−アリル−２−メチル−４−オキソ−
２−シクロペンテニル（±）−シス，トランス−クリサ
ンサメート，住友化学〕，メオスリン〔フェンプロパト
リン，（ＲＳ）−α−シアノ−３−フェノキシベンジル
２,２,３,３−テトラメチルシクロプロパンカルボキ
シレート，住友化学〕，フルシトリネート〔ペイ・オ
フ，（ＲＳ）−α−シアノ−３−フェノキシベンジル
（Ｓ）−２−（４−ジフルオロメトキシフェニル）−３
−メチルブチレート，エー・シー・シー社（American C
yanamid Co.）〕，エトフェンプロックス〔トレボン，
２−（４−エトキシフェニル）−２−メチルプロピル
３−フェノキシベンジル エーテル，三井東圧〕，クリ
スロンホルテ〔ｄ−レスメトリン，５−ベンジル−３−
フリルメチル（1RS,3RS,1RS,3SR）−２,２−ジメチル−
３−（２−メチルプロペン−１−イル）シクロプロパン
カルボキシレート，住友化学〕，天然ピレトリン〔ピレ
トリンＩ＋ピレトリンII〕などが例示される。Carbofuran insecticides include, for example, flathiocarb [butyl 2,3-dihydro-2,2
-Dimethylbenzofuran-7-yl N, N'-dimethyl-N, N'-thiodicarbamate, Ciba-Geigy Company],
Carbofuran [2,3-dihydro-2,2-dimethylbenzofuran-7-yl N-methylcarbamate, F.
FMC Corp., Bayer A
G)], carbosulfan [Advantage, 2,3-dihydro-2,2-dimethylbenzofuran-7-yl N-
(Dibutylaminothio) -N-methylcarbamate, FMC Co.], aminosulfuran [oncol, aminofuracarb, ethyl N- [N '-(2,3-dihydro-2,2-dimethylbenzofuran- 7-yloxycarbonyl) -N′-methylaminothio] -N-isopropyl β-alaninate, Otsuka Pharmaceutical Co., Ltd., and the like. Examples of the pyrethroid insecticide include allethrin [(±) -3-allyl-2-methyl-4-oxo-).
2-Cyclopentenyl (±) -cis, trans-chrysansamate, Sumitomo Chemical], meosulin [phenpropatrine, (RS) -α-cyano-3-phenoxybenzyl 2,2,3,3-tetramethylcyclopropane Carboxylate, Sumitomo Chemical], flucitrinate [Pay-off, (RS) -α-cyano-3-phenoxybenzyl (S) -2- (4-difluoromethoxyphenyl) -3]
-Methyl butyrate, ACC
yanamid Co.)], etofenprox [trebon,
2- (4-ethoxyphenyl) -2-methylpropyl
3-phenoxybenzyl ether, Mitsui Toatsu], chryslonforte [d-resmethrin, 5-benzyl-3-
Furylmethyl (1RS, 3RS, 1RS, 3SR) -2,2-dimethyl-
Examples include 3- (2-methylpropen-1-yl) cyclopropanecarboxylate, Sumitomo Chemical], natural pyrethrin [pyretrin I + pyretrin II], and the like.
【００１２】カルバメート系殺虫剤としては、たとえ
ば、ＢＰＭＣ〔ｏ−sec−ブチルフェニル Ｎ−メチル
カルバメート，クミアイ化学〕，ＭＩＰＣ〔ｏ−クメニ
ル Ｎ−メチルカルバメート，三菱化成〕，ＮＡＣ〔カ
ルバリル，１−ナフチル Ｎ−メチルカルバメート，ユ
ニオン・カーバイド社（Union Carbide Corp.）〕，カ
ルタップ〔Ｓ,Ｓ'−〔２−（ジメチルアミノ）トリメチ
レン〕ビス（チオカルバメート），武田薬品〕，ルーバ
ン〔Ｓ,Ｓ'−〔２−（ジメチルアミノ）トリメチレン〕
ビス（ベンゼンチオスルホネート），武田薬品〕などが
例示される。親油性の有機リン系殺虫剤としてはたとえ
ば、スミチオン〔ＭＥＰ，ジメチル４−ニトロ−ｍ−ト
リル ホスホロチオロチオネート，住友化学〕，マラソ
ン〔Ｓ−１,２−ビス（エトキシカルボニル）エチル
ジメチル ホスホロチオロチオネート，エー・シー・シ
ー社〕，エルサン〔ＰＡＰ，Ｓ−〔α−（エトキシカル
ボニル）ベンジル〕ジメチル ホスホロチオロチオネー
ト，モンテカチーニ・エジソン社（Montecatini Ediso
n）〕，ピラクロホス〔Ｏ−〔１−（４−クロロフェニ
ル）−４−ピラゾリル〕Ｏ−エチル Ｓ−プロピル ホ
スホロチオネート，武田薬品〕，ダイアジノン〔ジエチ
ル ２−イソプロピル−４−メチル−６−ピリミジニル
ホスホロチオネート，チバ・ガイギー社〕などが例示
される。Examples of carbamate insecticides include BPMC [o-sec-butylphenyl N-methylcarbamate, Kumiai chemistry], MIPC [o-cumenyl N-methylcarbamate, Mitsubishi Kasei], NAC [carbaryl, 1-naphthyl]. N-Methylcarbamate, Union Carbide Corp.], Cartap [S, S '-[2- (dimethylamino) trimethylene] bis (thiocarbamate), Takeda Yakuhin], Louban [S, S'- [2- (dimethylamino) trimethylene]
Bis (benzenethiosulfonate), Takeda Pharmaceutical Co., Ltd., and the like. Examples of lipophilic organophosphorus insecticides include Sumithion [MEP, dimethyl 4-nitro-m-tolyl phosphorothiolothioneate, Sumitomo Chemical], Marathon [S-1,2-bis (ethoxycarbonyl) ethyl.
Dimethyl phosphorothiolothionate, ACC Inc.], Elsan [PAP, S- [α- (ethoxycarbonyl) benzyl] dimethyl phosphorothiorothionate, Montecatini Ediso Inc.
n)], pyraclophos [O- [1- (4-chlorophenyl) -4-pyrazolyl] O-ethyl S-propyl phosphorothionate, Takeda Yakuhin], diazinone [diethyl 2-isopropyl-4-methyl-6-pyrimidinyl] Phosphorothionate, Ciba-Geigy Co., Ltd., etc.
【００１３】本発明におけるもうひとつの必須成分であ
る有機化合物〔II〕は、水に対する上記活性成分〔Ｉ〕
の分配係数が１０2以上のものをいう。化合物〔II〕は
農薬活性がなく、かつ高い沸点を有するものが用いら
れ、常温（以下、特にことわりのない場合、常温は１５
℃を意味する）で液体である化合物がより好ましい。こ
こで分配係数とは、脂溶性の尺度として通常使用される
分配係数のことであり、化学大辞典〔化学大辞典編集委
員会編，共立出版，第８巻，209頁，昭和37年〕に記載
の「分配律」における定数をいう。すなわち、化学大辞
典では分配律は「実際上混ざり合わない２種の液体に第
三物質（溶質）が溶け、これらが共存している場合、一
定温度ではその濃度に関係なく、これらの二つの溶液中
の濃度の比が一定になる」と定義されていて、この分配
律における定数を分配係数という。本発明における「分
配係数」もこのように定義された分配係数である。本発
明においては２種の液体が水田の水と有機化合物〔I
I〕，溶質が活性成分〔Ｉ〕に相当し、常温における有
機化合物〔II〕に対する活性成分〔Ｉ〕の濃度をＣｏ，
水に対する活性成分〔Ｉ〕の濃度をＣｗとすると、分配
係数はＣｏ／Ｃｗで表すことができる。すなわち本発明
における有機化合物〔II〕とはＣｏ／Ｃｗ≧１０2であ
るような有機化合物をいう。本発明における化合物〔I
I〕の分配係数Ｃｏ／Ｃｗの値の上限が特にないが、１
０7以下であることが好ましい。換言すると好ましい有
機化合物〔II〕の条件は１０2≦Ｃｏ／Ｃｗ≦１０7（常
温）である。また、さらに好ましい範囲は１０3≦Ｃｏ
／Ｃｗ≦１０6（常温）である。ここでも常温は１５℃
を意味する。活性成分〔Ｉ〕に対する分配係数が１０2
以上，好ましくは１０7以下である有機化合物〔II〕の
うち、以下の条件を具えた常温で液体の化合物が特に好
ましい。 ｉ）常温における水に対する溶解度が５％（重量％）以
下。 ii）沸点１６０℃以上。 iii）常温において活性成分〔Ｉ〕を１％（重量％）以
上溶解させる。The organic compound [II], which is another essential component in the present invention, is the active component [I] for water.
Has a distribution coefficient of 10 2 or more. As the compound [II], one having no pesticidal activity and a high boiling point is used, and it is at room temperature (hereinafter, room temperature is 15% unless otherwise specified).
Compounds that are liquid at (meaning ° C) are more preferred. Here, the partition coefficient is a partition coefficient that is usually used as a measure of fat solubility, and is described in the Chemistry Dictionary (edited by the Chemistry Dictionary Editing Committee, Kyoritsu Shuppan, Vol. 8, 209, Showa 37). Refers to the constant in the "Distribution Law" described. In other words, in the dictionary of chemistry, the partition law is that "when a third substance (solute) is dissolved in two types of liquids that are practically immiscible and they coexist, at a constant temperature these two It is defined that the ratio of the concentrations in the solution becomes constant. ”The constant in this partition law is called the partition coefficient. The “distribution coefficient” in the present invention is also the distribution coefficient defined in this way. In the present invention, two kinds of liquids are water of paddy field and organic compound [I
I], the solute corresponds to the active ingredient [I], and the concentration of the active ingredient [I] to the organic compound [II] at room temperature is Co,
When the concentration of the active ingredient [I] with respect to water is Cw, the partition coefficient can be expressed by Co / Cw. That is, the organic compound [II] in the present invention means an organic compound such that Co / Cw ≧ 10 2 . The compound [I
There is no upper limit on the value of the distribution coefficient Co / Cw of [I], but 1
It is preferably 0 7 or less. In other words, the preferable condition of the organic compound [II] is 10 2 ≦ Co / Cw ≦ 10 7 (normal temperature). A more preferable range is 10 3 ≦ Co
/ Cw ≦ 10 6 (normal temperature). Again, room temperature is 15 ° C
Means Partition coefficient for active ingredient [I] is 10 2
Among the above-mentioned organic compounds [II], which are preferably 10 7 or less, compounds which are liquid at room temperature under the following conditions are particularly preferable. i) The solubility in water at room temperature is 5% (% by weight) or less. ii) Boiling point of 160 ° C or higher. iii) Dissolve 1% (wt%) or more of the active ingredient [I] at room temperature.
【００１４】このような条件を具えた有機化合物〔II〕
としては、たとえば式 Ｒ1ＣＯＯＲ2〔式中、Ｒ1は
直鎖状または分枝状のＣ8-24アルキル基またはＣ8-24ア
ルケニル基を、Ｒ2は直鎖状または分枝状のＣ2-12アル
キル基を示す〕で表される脂肪酸エステル類〔III〕、 式Organic compound having such conditions [II]
Is, for example, a compound of the formula R 1 COOR 2 [wherein R 1 is a linear or branched C 8-24 alkyl group or a C 8-24 alkenyl group, and R 2 is a linear or branched C 8-24 alkyl group or a C 8-24 alkenyl group. C 2-12 alkyl group], a fatty acid ester [III] represented by the formula:
【化２５】 〔式中、Ｒ3は直鎖状または分枝状のＣ2-12アルキル基
を、ｍは２〜４の整数を示す〕で表されるジエステル類
〔IV〕、 式[Chemical 25] [Wherein R 3 represents a linear or branched C 2-12 alkyl group, and m represents an integer of 2 to 4], and a diester [IV] represented by the formula:
【化２６】 〔式中、Ｒ4，Ｒ5，Ｒ6は同一または異なって直鎖状ま
たは分枝状のＣ3-12アルキル基，Ｃ1-4塩化アルキル基
またはフェニル基を示す〕で表されるリン酸エステル類
〔Ｖ〕、[Chemical formula 26] [Wherein R 4 , R 5 and R 6 are the same or different and each represents a linear or branched C 3-12 alkyl group, C 1-4 chloroalkyl group or phenyl group] Acid esters [V],
【００１５】式Expression
【化２７】 〔式中、Ｒ7は直鎖状または分枝状のＣ2-16アルキル
基，ｎはＲ7基が１〜４個置換していることを示す〕で
表されるアルキルベンゼン類〔VI〕、 式[Chemical 27] [Wherein, R 7 represents a linear or branched C 2-16 alkyl group, and n represents that 1 to 4 R 7 groups are substituted], an alkylbenzene compound [VI], formula
【化２８】 〔式中、Ｒ8，Ｒ9，Ｒ10は水素原子または直鎖状もしく
は分枝状のＣ1-3アルキル基を、ｐ，ｑはＲ8，Ｒ9基が
１〜３個置換していることを示す〕で表されるジフェニ
ルメタン類〔VII〕、[Chemical 28] [In the formula, R 8 , R 9 and R 10 are hydrogen atoms or linear or branched C 1-3 alkyl groups, and p and q are substituted by 1 to 3 R 8 and R 9 groups. The diphenylmethanes [VII],
【００１６】式Expression
【化２９】 〔式中、Ｒ11は直鎖状または分枝状のＣ1-12アルキル基
を示す〕で表される安息香酸エステル類〔VIII〕、 式[Chemical 29] [In the formula, R 11 represents a linear or branched C 1-12 alkyl group], benzoic acid esters [VIII],
【化３０】 〔式中、Ｒ12，Ｒ13はそれぞれ直鎖状または分枝状のＣ
1-12アルキル基を示す〕で表されるフタル酸エステル類
〔IX〕などが挙げられる。Embedded image [In the formula, R 12 and R 13 are each linear or branched C
1-12 alkyl group] and phthalates [IX] and the like.
【００１７】式 Ｒ1ＣＯＯＲ2で表される脂肪酸エステ
ル類〔III〕におけるＣ8-24アルキル基（Ｒ1）として
は、Ｃ9-19アルキル基がより好ましく、たとえばノニ
ル，ウンデシル，トリデシル，ペンタデシル，ヘプタデ
シルなどがあげられる。同じくＣ8-24アルケニル基（Ｒ
1）としては、Ｃ15-19アルケニル基がより好ましく、た
とえばオレイル〔Ｃ8Ｈ17ＣＨ＝ＣＨ（ＣＨ2）7−〕，
リノレイル〔Ｃ5Ｈ11ＣＨ＝ＣＨＣＨ2ＣＨ＝ＣＨ（ＣＨ
2）7−〕などがあげられる。同じくＣ2-12アルキル基
（Ｒ2）としては、Ｃ3-8アルキル基がより好ましく、た
とえばブチル，アミル，ヘキシル，ヘプチルなどがあげ
られる。したがって、脂肪酸エステル類〔III〕として
はたとえば、ラウリン酸アミル，ミリスチン酸アミル，
パルミチン酸ブチル，パルミチン酸アミル，パルミチン
酸ヘキシル，ステアリン酸ブチル，ステアリン酸アミ
ル，ステアリン酸ヘキシル，オレイン酸ブチル，オレイ
ン酸アミル，リノール酸ブチルなどが例示される。The C 8-24 alkyl group (R 1 ) in the fatty acid ester [III] represented by the formula R 1 COOR 2 is more preferably a C 9-19 alkyl group, for example, nonyl, undecyl, tridecyl, pentadecyl. , Heptadecyl, etc. Similarly C 8-24 alkenyl group (R
The 1), more preferably C 15-19 alkenyl group, for example, oleyl [C 8 H 17 CH = CH ( CH 2) 7 - ],
Linoleyl [C 5 H 11 CH = CHCH 2 CH = CH (CH
2) 7 -], and the like. Similarly, the C 2-12 alkyl group (R 2 ) is more preferably a C 3-8 alkyl group, and examples thereof include butyl, amyl, hexyl and heptyl. Therefore, examples of the fatty acid esters [III] include amyl laurate, amyl myristate,
Examples include butyl palmitate, amyl palmitate, hexyl palmitate, butyl stearate, amyl stearate, hexyl stearate, butyl oleate, amyl oleate, butyl linoleate and the like.
【００１８】式Expression
【化３１】 で表されるジエステル類〔IV〕におけるＣ2-12アルキル
基（Ｒ3）としては、Ｃ2-10アルキル基がより好まし
く、たとえばエチル，プロピル，ブチル，アミル，ヘキ
シル，ヘプチル，オクチルなどがあげられる。したがっ
て、ジエステル類〔IV〕としてはたとえば、コハク酸ジ
エチル，コハク酸ジプロピル，コハク酸ジブチル，コハ
ク酸ジアミル，コハク酸ジオクチル，グルタル酸ジエチ
ル，グルタル酸ジブチル，グルタル酸ジアミル，グルタ
ル酸ジオクチル，アジピン酸ジブチル，アジピン酸ジア
ミル，アジピン酸ジオクチルなどが例示される。[Chemical 31] The C 2-12 alkyl group (R 3 ) in the diester [IV] represented by is more preferably a C 2-10 alkyl group, and examples thereof include ethyl, propyl, butyl, amyl, hexyl, heptyl and octyl. To be Therefore, examples of the diesters [IV] include diethyl succinate, dipropyl succinate, dibutyl succinate, diamyl succinate, dioctyl succinate, diethyl glutarate, dibutyl glutarate, diamyl glutarate, dioctyl glutarate, dibutyl adipate. , Diamyl adipate, dioctyl adipate and the like.
【００１９】式Expression
【化３２】 で表されるリン酸エステル類〔Ｖ〕におけるＣ3-12アル
キル基（Ｒ4，Ｒ5，Ｒ6）としては、Ｃ4-9アルキル基が
より好ましく、たとえばブチル，アミル，ヘキシル、オ
クチルなどがあげられる。同じくＣ1-4塩化アルキル基
（Ｒ4，Ｒ5，Ｒ6）としてはＣ2-3塩化アルキル基がより
好ましく、たとえばトリクロロエチル，トリクロロプロ
ピルなどがあげられる。したがって、リン酸エステル類
〔Ｖ〕としてはたとえば、トリブチルホスフェート，ト
リアミルホスフェート，トリオクチルホスフェート，ブ
チルジフェニルホスフェート，オクチルジフェニルホス
フェート，トリ（クロロエチル）ホスフェートなどが例
示される。Embedded image The C 3-12 alkyl group (R 4 , R 5 , R 6 ) in the phosphoric acid ester [V] represented by is more preferably a C 4-9 alkyl group such as butyl, amyl, hexyl and octyl. Can be given. Similarly, as the C 1-4 chloroalkyl group (R 4 , R 5 , R 6 ), a C 2-3 chloroalkyl group is more preferable, and examples thereof include trichloroethyl and trichloropropyl. Therefore, examples of the phosphoric acid ester [V] include tributyl phosphate, triamyl phosphate, trioctyl phosphate, butyl diphenyl phosphate, octyl diphenyl phosphate, tri (chloroethyl) phosphate and the like.
【００２０】式Expression
【化３３】 で表されるアルキルベンゼン類〔VI〕におけるＣ2-16ア
ルキル基（Ｒ7）としてはＣ2-10アルキル基がより好ま
しく、たとえばエチル，プロピル，イソプロピル，ブチ
ル，イソブチル，sec−ブチル，tert−ブチル，アミ
ル，イソアミル，tert−アミル，オクチル，デシルなど
があげられる。化合物〔VI〕はこれらの基が同一または
異なって１〜４個置換したベンゼンである。したがっ
て、アルキルベンゼン類〔VI〕としては、たとえば、ジ
エチルベンゼン，ジイソプロピルベンゼン，トリイソプ
ロピルベンゼン，tert−ブチルベンゼン，ジ（tert−ブ
チル）ベンゼン，ジアミルベンゼン，トリアミルベンゼ
ン，テトラアミルベンゼン，tert−アミルベンゼン，ジ
（tert−アミル）ベンゼン，オクチルベンゼン，ドデシ
ルベンゼン，ジドデシルベンゼンなどが例示される。[Chemical 33] The C 2-16 alkyl group (R 7 ) in the alkylbenzenes [VI] represented by is more preferably a C 2-10 alkyl group, for example, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl. , Amyl, isoamyl, tert-amyl, octyl, decyl and the like. The compound [VI] is benzene in which 1 to 4 of these groups are the same or different and are substituted. Therefore, examples of the alkylbenzenes [VI] include diethylbenzene, diisopropylbenzene, triisopropylbenzene, tert-butylbenzene, di (tert-butyl) benzene, diamylbenzene, triamylbenzene, tetraamylbenzene, tert-amylbenzene. , Di (tert-amyl) benzene, octylbenzene, dodecylbenzene, didodecylbenzene and the like.
【００２１】式Expression
【化３４】 で表されるジフェニルメタン類〔VII〕におけるＣ1-3ア
ルキル基（Ｒ8，Ｒ9，Ｒ10）としては、メチル，エチ
ル，プロピル，イソプロピルがあげられる。Ｒ8がＣ1-3
アルキル基で、２〜３個置換されている場合はこれらの
Ｃ1-3アルキル基は同一でも、また異なっていてもよ
い。Ｒ9がＣ1-3アルキル基で、２〜３個置換されている
場合も同様にこれらのＣ1-3アルキル基は同一でも、ま
た異なっていてもよい。したがって、ジフェニルメタン
類〔VII〕としては、たとえば、フェニルキシリルエタ
ン，フェニルキシリルプロパン，トリルキシリルエタ
ン，ジキシリルメタン，ジイソキシリルエタンなどが例
示される。Embedded image Examples of the C 1-3 alkyl group (R 8 , R 9 , R 10 ) in the diphenylmethanes [VII] represented by are methyl, ethyl, propyl and isopropyl. R 8 is C 1-3
When 2 to 3 alkyl groups are substituted, these C 1-3 alkyl groups may be the same or different. Similarly, when R 9 is a C 1-3 alkyl group and a few of them are substituted, these C 1-3 alkyl groups may be the same or different. Therefore, examples of the diphenylmethanes [VII] include phenylxylylethane, phenylxylylpropane, tolylxylylethane, dixylylmethane, diisoxylylethane and the like.
【００２２】式Expression
【化３５】 で表される安息香酸エステル類〔VIII〕のＣ1-12アルキ
ル基（Ｒ11）としては、Ｃ1-8アルキル基がより好まし
く、たとえばメチル，エチル，ブチル，アミル，ヘキシ
ル，オクチル，ノニルなどがあげられる。したがって、
安息香酸エステル類〔VIII〕としては、たとえば、安息
香酸メチル，安息香酸エチル，安息香酸ブチル，安息香
酸アミル，安息香酸ヘキシル，安息香酸オクチル，安息
香酸ノニルなどが例示される。Embedded image The C 1-12 alkyl group (R 11 ) of benzoic acid ester [VIII] represented by is more preferably a C 1-8 alkyl group, for example, methyl, ethyl, butyl, amyl, hexyl, octyl, nonyl, etc. Can be given. Therefore,
Examples of benzoic acid esters [VIII] include methyl benzoate, ethyl benzoate, butyl benzoate, amyl benzoate, hexyl benzoate, octyl benzoate, nonyl benzoate and the like.
【００２３】式Expression
【化３６】 で表されるフタル酸エステル類〔IX〕のＣ1-12アルキル
基（Ｒ12，Ｒ13）としてはＣ1-8アルキル基がより好ま
しく、たとえばメチル，エチル，ブチル，アミル，ヘキ
シル，オクチルなどがあげられる。したがって、フタル
酸エステル類〔IX〕としては、たとえばフタル酸ジメチ
ル，フタル酸ジエチル，フタル酸ジブチル，フタル酸ジ
オクチルなどが例示される。上記した有機化合物〔II〕
は一種だけ用いてもよいし、また二種以上を混合して用
いてもよい。Embedded image The C 1-12 alkyl group (R 12 , R 13 ) of the phthalate ester [IX] represented by is more preferably a C 1-8 alkyl group, for example, methyl, ethyl, butyl, amyl, hexyl, octyl, etc. Can be given. Therefore, examples of the phthalates [IX] include dimethyl phthalate, diethyl phthalate, dibutyl phthalate, dioctyl phthalate and the like. Organic compounds mentioned above [II]
May be used alone or in combination of two or more.
【００２４】[0024]
【発明の実施の形態】本発明の農薬製剤は、前記した農
薬活性成分〔Ｉ〕と有機化合物〔II〕のほか必要ならば
後記するような担体を公知の方法もしくはそれに準ずる
方法にて混合することにより製造することができる。こ
の製剤に含まれる有機化合物〔II〕の量が少なすぎる場
合は魚介類に対する毒性を軽減する効果が充分でなく、
また多すぎる場合は使用時に不都合があり、またコスト
高になる。したがって、農薬活性成分１部（以下、部は
すべて重量部を示す）に対して通常、有機化合物〔II〕
を０.１〜５部，好ましくは０.２〜３部用いる。また、
得られる製剤は通常、固形製剤、すなわち、粉剤，粉粒
剤，粒剤などであり、粉粒剤，粒剤がより好ましい。本
製剤全体に対する農薬活性成分〔Ｉ〕の配合割合は水と
有機化合物〔II〕に対する活性成分〔Ｉ〕の分配係数と
使用量および水田における活性成分〔Ｉ〕の許容濃度に
より適宜きめられるが、通常、全量を１００部として活
性成分〔Ｉ〕は０.０１〜１０部である。BEST MODE FOR CARRYING OUT THE INVENTION In the pesticidal preparation of the present invention, the pesticidal active ingredient [I] and the organic compound [II] described above and, if necessary, the following carriers are mixed by a known method or a method analogous thereto. It can be manufactured. If the amount of the organic compound [II] contained in this formulation is too small, the effect of reducing toxicity to seafood is not sufficient,
On the other hand, if the amount is too large, there will be inconvenience in use and the cost will increase. Therefore, the organic compound [II] is usually added to 1 part of the pesticide active ingredient (hereinafter, all parts indicate parts by weight).
Is used in an amount of 0.1 to 5 parts, preferably 0.2 to 3 parts. Also,
The obtained preparations are usually solid preparations, that is, powders, powders, granules and the like, and powders and granules are more preferable. The ratio of the pesticide active ingredient [I] to the whole preparation is appropriately determined depending on the distribution coefficient and the amount of the active ingredient [I] used with respect to water and the organic compound [II] and the allowable concentration of the active ingredient [I] in the paddy field. Usually, the active ingredient [I] is 0.01 to 10 parts based on the total amount of 100 parts.
【００２５】本発明の製剤が水田で使用された場合、ど
のようにして農薬活性成分の魚介類に対する毒性を軽減
するかについては明らかではないが、カルボフラン系殺
虫剤やピレスロイド系殺虫剤などの殺虫成分を例にとる
と、たとえばつぎのように考えることができる。すなわ
ち、本発明の農薬製剤をたとえば水田に散布すると前記
した分配係数に従って上記の殺虫成分〔Ｉ〕は水田の水
および有機化合物〔II〕とに分配され、水中での殺虫成
分〔Ｉ〕の濃度は魚介類に対する毒性が問題にならない
程度に保たれる。しかるに、殺虫成分〔Ｉ〕は作物の根
より徐々に吸収され根茎部に蓄積され、このような根茎
を害虫が摂取することにより殺虫成分が害虫の体内にと
りこまれて十分な殺虫作用を示すことになる。一方、水
中の殺虫成分〔Ｉ〕は作物の根に吸収されても有機化合
物〔II〕に分配されている部分から分配係数にみあう量
だけ水中に常に溶出しつづけ、水中での毒性が問題にな
らなくてしかも害虫に対しては有効であるという濃度を
長時間保つことになる。Although it is not clear how the formulation of the present invention reduces the toxicity of pesticidal active ingredients to seafood when used in paddy fields, insecticides such as carbofuran insecticides and pyrethroid insecticides. Taking the components as an example, the following can be considered. That is, when the pesticide formulation of the present invention is applied to a paddy field, for example, the insecticidal component [I] is distributed between the paddy field water and the organic compound [II] according to the above-mentioned partition coefficient, and the concentration of the insecticidal component [I] in the water is increased. Is maintained to such an extent that toxicity to seafood is not an issue. However, the insecticidal component [I] is gradually absorbed from the roots of crops and accumulated in the rhizome, and when the insect pest ingests such rhizome, the insecticidal component is taken into the body of the insect pest and exhibits a sufficient insecticidal action. become. On the other hand, the insecticidal component [I] in water continues to be eluted in water in an amount matching the partition coefficient from the part distributed to the organic compound [II] even if it is absorbed by the roots of crops, which causes toxicity in water. However, the concentration that is effective against pests is maintained for a long time.
【００２６】本発明の製剤を製造する場合に用いられる
担体としては、たとえば、希釈剤，増量剤などの固体担
体があげられる。このような担体としては、たとえば、
植物性粉末（たとえば、米糠，大豆粉，タバコ粉，小麦
粉，澱粉，木粉など），鉱物性粉末（たとえば、カオリ
ン，ベントナイト，リン酸カルシウム，酸性白土などの
クレイ類，滑石粉，ロウ石粉などのタルク類，硅藻土，
雲母粉などのシリカ類など），さらにアルミナ，硫黄粉
末，活性炭なども用いられ、これらは一種または二種以
上を（製剤中に５〜９０％、好ましくは１０〜８０％）
混合して使用しうる。また、各種界面活性剤，溶剤など
を適宜加えてもよい。また必要に応じて非親油性農薬活
性成分を加えてもよい。このような非親油性活性成分と
しては、たとえば、非親油性の天然殺虫剤，非親油性の
有機リン系殺虫剤，トリシクラゾール系殺菌剤，ベンズ
イミダゾール系殺菌剤，銅系殺菌剤，抗生物質，非親油
性の有機リン系殺菌剤などがあげられる。本発明の農薬
製剤は、以上述べたように魚介類に対する毒性を軽減し
た製剤であるが、簡易かつ安価に製造することができ、
さらには長期間の保存後においても適確に、しかもすぐ
れた作用と魚介類に対する毒性軽減の効果を奏しうるか
ら、当業界における有用性はきわめて大きいといえる。Examples of the carrier used for producing the preparation of the present invention include solid carriers such as diluents and fillers. As such a carrier, for example,
Vegetable powder (for example, rice bran, soybean powder, tobacco powder, wheat flour, starch, wood flour, etc.), mineral powder (for example, kaolin, bentonite, calcium phosphate, clay such as acid clay, talc powder, talc such as wax stone powder) , Diatomaceous earth,
Silicas such as mica powder, etc.), alumina, sulfur powder, activated carbon, etc. are also used, and one or more of these may be used (5 to 90% in the formulation, preferably 10 to 80%).
It can be used as a mixture. Further, various surfactants, solvents, etc. may be added as appropriate. Moreover, you may add a non-lipophilic pesticide active ingredient as needed. Examples of such non-lipophilic active ingredients include non-lipophilic natural insecticides, non-lipophilic organophosphorus insecticides, tricyclazole-based fungicides, benzimidazole-based fungicides, copper-based fungicides, antibiotics, Examples include non-lipophilic organic phosphorus bactericides. The pesticide formulation of the present invention is a formulation with reduced toxicity to seafood as described above, but can be produced easily and inexpensively,
Further, it can be said to be extremely useful in the art, since it can exhibit an excellent action and an effect of reducing toxicity to fish and shellfish even after storage for a long period of time.
【００２７】[0027]
【実施例】本発明は、さらに下記の実施例，試験例で詳
しく説明されるが、これらの例は単なる実例であって本
発明を限定するものではなく、また本発明の範囲を逸脱
しない範囲で変化させてもよい。なお、部は重量部を表
す。EXAMPLES The present invention will be further described in detail with reference to the following examples and test examples, but these examples are merely illustrative and do not limit the present invention, and do not depart from the scope of the present invention. You may change with. In addition, a part represents a weight part.
【００２８】[0028]
【実施例１】フラチオカルブ５部にオレイン酸アミル３
部，カオリナイトクレイ８７部，ポリビニルアルコール
（以下、ＰＶＡと略す）５部を加えて均一混合し、水１
４部を注加して練合したのち造粒し、ついで８０℃の熱
風で乾燥することにより粒剤を得る。Example 1 Amyl oleate 3 in 5 parts of flathiocarb
Parts, 87 parts of kaolinite clay, 5 parts of polyvinyl alcohol (hereinafter abbreviated as PVA), and uniformly mixed to prepare water 1
Granules are obtained by pouring and kneading 4 parts, granulating, and then drying with hot air at 80 ° C.
【実施例２】混合機にシリカ粒９０部を入れてかきまぜ
ながら、あらかじめフラチオカルブ５部にtert−アミル
ベンゼン５部を加えて均一混合したものを吸着させて粉
粒剤を得る。Example 2 90 parts of silica particles were placed in a mixer and stirred, and 5 parts of tert-amylbenzene was added in advance to 5 parts of flathiocarb and the mixture was uniformly adsorbed to obtain a powdery or granular material.
【実施例３】混合機にライトン粒（ライトストンK.K.
製）９０部を入れてかきまぜながら、あらかじめフラチ
オカルブ５部にオクチルジフェニルホスフェート５部を
加えて均一混合したものを吸着させて粒剤を得る。[Embodiment 3] Ryton grains (Rightstone KK
Granules are obtained by admixing with 90 parts of a mixture of 5 parts of flathiocarb and 5 parts of octyldiphenyl phosphate in advance and stirring them uniformly.
【実施例４】混合機にライトン粒９３.５部を入れてか
きまぜながら、あらかじめフラチオカルブ５部にオクチ
ルジフェニルホスフェート１部，コハク酸ジエチル０.
５部を加えて均一混合したものを吸着させて粉粒剤を得
る。Example 4 93.5 parts of Ryton granules were put in a mixer and stirred, while 5 parts of fratiocarb were preliminarily mixed with 1 part of octyldiphenyl phosphate and 0.1 part of diethyl succinate.
5 parts were added and the mixture was uniformly adsorbed to obtain a powdery granule.
【実施例５】混合機にライトン粒９３部を入れてかきま
ぜながら、あらかじめフラチオカルブ２部にフェニルキ
シリルエタン５部を加えて均一混合したものを吸着させ
て粉粒剤を得る。Example 5 93 parts of Ryton grains are put into a mixer and stirred, and 2 parts of flathiocarb and 5 parts of phenylxylylethane are added in advance and uniformly mixed to obtain a powder or granule.
【００２９】[0029]
【実施例６】混合機にライトン粒９０部を入れてかきま
ぜながら、あらかじめフラチオカルブ５部にフェニルキ
シリルエタン５部を加えて均一混合したものを吸着させ
て粒剤を得る。Example 6 90 parts of Ryton granules were put into a mixer and stirred, and 5 parts of phenylxylylethane was previously added to 5 parts of flathiocarb and the resulting mixture was adsorbed to obtain granules.
【実施例７】フラチオカルブ５部に滑石クレイ８５部お
よびアルファー化澱粉５部を加え、水１４部を注加した
のち造粒機で造粒し、ついで８０℃の熱風で乾燥して粒
剤を製造する。この粒剤に安息香酸エチル５部を吸着さ
せて粒剤を得る。Example 7 85 parts of talc clay and 5 parts of pregelatinized starch were added to 5 parts of fratiocarb, 14 parts of water was added, and the mixture was granulated with a granulator and then dried with hot air at 80 ° C. to give granules. To manufacture. 5 parts of ethyl benzoate is adsorbed on this granule to obtain a granule.
【実施例８】混合機にカガライト粒（丹後建設K.K.製）
９３部を入れてかきまぜながら、あらかじめフラチオカ
ルブ２部にアジピン酸ジオクチル５部を加えて均一混合
したものを吸着させて粒剤を得る。[Embodiment 8] Kagalite grains (manufactured by Tango Construction KK) in a mixer
While stirring and adding 93 parts, 5 parts of dioctyl adipate and 5 parts of dioctyl adipate were mixed in advance and adsorbed to obtain a granule.
【実施例９】カルボスルファン１.５部にオクチルジフ
ェニルホスフェート５部，滑石クレイ８８.５部および
アルファー化澱粉５部を加えて均一混合し、水１４部を
注加して練合したのち造粒機で造粒し、ついで８０℃の
熱風で乾燥することにより粒剤を得る。Example 9 To 1.5 parts of carbosulfan, 5 parts of octyldiphenyl phosphate, 88.5 parts of talc clay and 5 parts of pregelatinized starch were added and uniformly mixed, and 14 parts of water was added and kneaded. Granules are obtained by granulating with a granulator and then drying with hot air at 80 ° C.
【実施例１０】混合機にカガライト粒９２部を入れてか
きまぜながら、あらかじめカルボフラン２部にトリオク
チルホスフェート６部を加えて均一混合したものを吸着
させて粒剤を得る。Example 10 92 parts of cagarite grains were put in a mixer and stirred, and 2 parts of carbofuran and 6 parts of trioctyl phosphate were added in advance and uniformly mixed to obtain a granule.
【００３０】[0030]
【実施例１１】フラチオカルブ５部にフェニルキシリル
エタン５部を加え均一混合する（混合物Ａ）。ポリエチ
レングリコール6000 ５部にトリシクラゾール５部を加
えて７０℃に加熱しながら均一混合する（混合物Ｂ）。
混合機中で混合物Ａをライトン粒８０部に吸着させたの
ち混合物Ｂをさらにかきまぜながら加えて粒剤を得る。Example 11 5 parts of phenylxylylethane is added to 5 parts of flathiocarb and uniformly mixed (mixture A). To 5 parts of polyethylene glycol 6000, 5 parts of tricyclazole are added and mixed uniformly while heating to 70 ° C. (mixture B).
The mixture A is adsorbed on 80 parts of Ryton grains in a mixer, and then the mixture B is added with further stirring to obtain granules.
【実施例１２】フラチオカルブ０.５部，安息香酸ヘキ
シル０.５部を滑石クレイ９９部に加えて粉粒剤を得
る。Example 12 0.5 part of fratiocarb and 0.5 part of hexyl benzoate are added to 99 parts of talc clay to obtain a powdery granule.
【実施例１３】フラチオカルブ５部にトリシクラゾール
５部，フェニルキシリルエタン５部，アルファー化澱粉
５部，滑石クレイ８０部を加えて均一混合し、水１４部
を注加して練合したのち造粒機で造粒し、ついで８０℃
の熱風で乾燥することにより粒剤を得る。Example 13 To 5 parts of fratiocarb, 5 parts of tricyclazole, 5 parts of phenylxylylethane, 5 parts of pregelatinized starch and 80 parts of talc clay were added and uniformly mixed, and 14 parts of water was added and kneaded, followed by production. Granulate with granulator, then 80 ℃
Granules are obtained by drying with hot air.
【実施例１４】フラチオカルブ５部に１,２,５,６−テ
トラヒドロピロロ〔３,２,１−ｉｊ〕キノリン−４−オ
ン（チバ・ガイギー社製殺菌剤，ＣＧ 114）５部，オク
チルジフェニルホスフェート５部，アルファー化澱粉５
部，滑石クレイ８０部を加えて均一混合し、水１４部を
注加して練合したのち造粒機で造粒し、ついで８０℃の
熱風で乾燥することにより粒剤を得る。Example 14 5 parts of flathiocarb and 1,2,5,6-tetrahydropyrrolo [3,2,1-ij] quinolin-4-one (Ciba Geigy bactericide, CG 114) 5 parts, octyldiphenyl 5 parts phosphate, 5 pregelatinized starch
And 80 parts of talc clay are added and mixed uniformly, 14 parts of water is added and kneaded, then granulated by a granulator, and then dried with hot air at 80 ° C. to obtain a granule.
【００３１】カルボフラン系殺虫剤についての対照製剤
は以下に示す。Control formulations for carbofuran insecticides are shown below.
【対照製剤１】混合機中でフラチオカルブ５部をアプル
ス（イソライトK.K.製）９５部に吸着させ粒剤を得る。[Control formulation 1] Granules are obtained by adsorbing 5 parts of furatiocarb to 95 parts of Aplus (made by Isolite KK) in a mixer.
【対照製剤２】フラチオカルブ５部に滑石クレイ９０
部，ＰＶＡ５部を加えて均一混合し、水１４部を注加し
て練合したのち造粒機で造粒し、ついで８０℃の熱風で
乾燥することにより粒剤を得る。[Control formulation 2] 5 parts of flathiocarb and 90 talc clay
Parts and 5 parts of PVA are added and uniformly mixed, 14 parts of water is added and kneaded, then granulated by a granulator, and then dried with hot air at 80 ° C. to obtain granules.
【対照製剤３】カルボフラン２部にアルファー化澱粉５
部，滑石クレイ９３部を加えて均一混合し、水１４部を
注加して練合したのち造粒機で造粒し、ついで８０℃の
熱風で乾燥することにより粒剤を得る。[Control formulation 3] Carbofuran 2 parts and pregelatinized starch 5
And 93 parts of talc clay are added and uniformly mixed, 14 parts of water is added and kneaded, then granulated with a granulator, and then dried with hot air at 80 ° C. to obtain granules.
【００３２】[0032]
【魚毒性試験】くみ置きした上水（２３−２６℃）を磁
器製ポット（内径２６cm，深さ３０cm）に入れる。水１
０リットル中に含まれる親油性農薬活性成分がそれぞれ
５mg，１０mg，２５mgになるように上記の製剤をはかり
とってポットに加える。３つのポットにマゴイ（体長
４.８−５.１cm，体重２.８−３.０ｇ）各５尾を放し２
４および４８時間後の魚の死亡数を数えて死魚率および
ＴＬｍ（半数致死濃度，median Tolerance Limit ５０
％死亡する濃度）を算出した。結果を〔表１〕に示す。
成績は上記の試験を２回行なった成績，すなわち計１０
尾についての結果である。なお、ＴＬｍ値は江上伸雄編
「実験動物としての魚類」，第387-392頁，ソフトサイ
エンス，1981年，に記載の算出方法により算出した。[Fish toxicity test] Put the tap water (23-26 ° C) placed in a pool into a porcelain pot (inner diameter 26 cm, depth 30 cm). Water 1
The above formulation is weighed and added to the pot so that the lipophilic pesticide active ingredient contained in 0 liter is 5 mg, 10 mg and 25 mg, respectively. Release 5 macaws (length 4.8-5.1 cm, weight 2.8-3.0 g) in 3 pots each 2
Mortality and TLm (half-lethal concentration, median Tolerance Limit 50) were calculated by counting the number of dead fish after 4 and 48 hours.
% Concentration at which death occurred) was calculated. The results are shown in [Table 1].
The result is the result of performing the above test twice, that is, a total of 10
This is the result for the tail. The TLm value was calculated by the calculation method described in Nobuo Egami, "Fish as Experimental Animals," pp. 387-392, Soft Science, 1981.
【００３３】[0033]
【表１】 [Table 1]
【００３４】[0034]
【実施例１５】混合機にシリカ粒９４部を入れてかきま
ぜながら、あらかじめフルシトリネート３部にフェニル
キシリルエタン３部を加えて均一混合したものを吸着さ
せて粒剤を得る。Example 15 94 parts of silica particles were put in a mixer and stirred, and 3 parts of phenylxylylethane was added to 3 parts of flucitrinate in advance and the mixture was uniformly adsorbed to obtain granules.
【実施例１６】フルシトリネート１.５部にオクチルジ
フェニルホスフェート２部，カオリナイトクレイ９１.
５部，ＰＶＡ５部を加えて均一混合し、水１４部を注加
して練合したのち造粒機で造粒し、ついで８０℃の熱風
で乾燥することにより粒剤を得る。Example 16: 1.5 parts of flucitrinate, 2 parts of octyldiphenyl phosphate, 91. kaolinite clay.
5 parts and 5 parts of PVA are added and uniformly mixed, 14 parts of water is added and kneaded, then granulated by a granulator, and then dried by hot air at 80 ° C. to obtain a granule.
【実施例１７】混合機にライトン粒９０部を入れてかき
まぜながら、あらかじめエトフェンプロックス５部にオ
クチルジフェニルホスフェート５部を加えて均一混合し
たものを吸着させて粒剤を得る。Example 17 90 parts of Ryton granules were put in a mixer and stirred, and 5 parts of octyldiphenyl phosphate was previously added to 5 parts of etofenprox and the mixture was uniformly adsorbed to obtain granules.
【実施例１８】混合機にシリカ粒９５.５部を入れてか
きまぜながら、あらかじめエトフェンプロックス２.５
部にフェニルキシリルエタン２部を加えて均一混合した
ものを吸着させて粒剤を得る。Example 18 95.5 parts of silica particles were put in a mixer and stirred, and etofenprox 2.5 was previously prepared.
2 parts of phenylxylylethane was added to the above parts and a homogeneous mixture was adsorbed to obtain granules.
【実施例１９】カオリナイトクレイ８８.５部にＰＶＡ
５部，水１３部を加えて、造粒機で造粒し、ついで９０
℃の熱風で乾燥することにより粒剤を製造する。あらか
じめフタル酸ジエチル２.５部にエトフェンプロックス
４部を加えて混合したものを上記の粒剤に吸着させて粒
剤を得る。Example 19 PVA was added to 88.5 parts of kaolinite clay.
Add 5 parts and 13 parts water and granulate with a granulator, then 90
Granules are manufactured by drying with hot air at ℃. Granules are obtained by previously admixing 2.5 parts of diethyl phthalate with 4 parts of etofenprox and mixing them to the above granules.
【００３５】[0035]
【実施例２０】エトフェンプロックス０.５部にオクチ
ルジフェニルホスフェート１部，カオリナイトクレイ９
５.５部，ＰＶＡ３部を加えて均一混合し、水１５部を
注加して練合したのち造粒機で造粒し、ついで８５℃の
熱風で乾燥することにより粒剤を得る。Example 20 Etofenprox 0.5 part, octyldiphenyl phosphate 1 part, kaolinite clay 9
5.5 parts and 3 parts of PVA are added and mixed uniformly, 15 parts of water is added and kneaded, then granulated by a granulator, and then dried by hot air at 85 ° C. to obtain granules.
【実施例２１】混合機にシリカ粒９１部を入れてかきま
ぜながら、あらかじめクリスロンホルテ３部にフェニル
キシリルエタン６部を加えて均一混合したものを吸着さ
せて粒剤を得る。Example 21 91 parts of silica particles are put into a mixer and stirred, and 3 parts of kryslonforte and 6 parts of phenylxylylethane are added in advance and uniformly mixed to obtain a granule.
【実施例２２】混合機にシリカ粒９４部を入れてかきま
ぜながら、あらかじめクリスロンホルテ３部にオクチル
ジフェニルホスフェート３部を加えて均一混合したもの
を吸着させて粒剤を得る。Example 22 94 parts of silica particles were put in a mixer and stirred, and 3 parts of octyldiphenyl phosphate was added in advance to 3 parts of kryslonforte and the mixture was uniformly adsorbed to obtain granules.
【実施例２３】混合機にライトン粒７５部を入れてかき
まぜながら、あらかじめ天然ピレトリン（活性成分とし
てピレトリンＩおよびピレトリンIIを計１８重量％含
む。大日本除虫菊製）２０部にオクチルジフェニルホス
フェート５部を加えて均一混合したものを吸着させて粒
剤を得る。Example 23 75 parts of Ryton granules were put in a mixer and stirred, and 20 parts of natural pyrethrin (containing 18% by weight of pyrethrin I and pyrethrin II as active ingredients in total, manufactured by Dainippon Pyrethrum) was previously added to 5 parts of octyldiphenyl phosphate. Granules are obtained by adsorbing the mixture obtained by adding and adsorbing.
【実施例２４】混合機中にライトン粒８５部を入れてか
きまぜながら、あらかじめ天然ピレトリン（実施例２３
で用いたもの）１０部にフェニルキシリルエタン５部を
加えて均一混合したものを吸着させて粒剤を得る。Example 24 85 parts of Ryton granules were put in a mixer and stirred, and the natural pyrethrin (Example 23) was mixed in advance.
5 parts of phenylxylylethane was added to 10 parts of that used in Example 1) and the mixture was uniformly mixed to obtain a granule.
【００３６】ピレトリン系殺虫剤についての対照製剤は
以下に示す。A control formulation for the pyrethrin insecticide is shown below.
【対照製剤４】混合機中でフルシトリネート３部をシリ
カ粒９７部に吸着させて粒剤を得る。[Control preparation 4] 3 parts of flucitrinate are adsorbed on 97 parts of silica particles in a mixer to obtain granules.
【対照製剤５】混合機中でエトフェンプロックス５部を
ライトン粒９５部に吸着させて粒剤を得る。[Control formulation 5] Granules are obtained by adsorbing 5 parts of etofenprox to 95 parts of Ryton granules in a mixer.
【対照製剤６】混合機中でクリスロンホルテ３部をシリ
カ粒９７部に吸着させて粒剤を得る。[Control formulation 6] 3 parts of kryslonforte is adsorbed on 97 parts of silica particles in a mixer to obtain granules.
【対照製剤７】混合機中で天然ピレトリン（実施例２３
で用いたもの）１０部をシリカ粒９０部に吸着させて粒
剤を得る。[Control formulation 7] Natural pyrethrin (Example 23
Granules are obtained by adsorbing 10 parts of those used in (1) to 90 parts of silica particles.
【００３７】[0037]
【魚毒性試験】前記した試験法で魚毒性試験を行なっ
た。２４，４８，７２および９６時間後の魚の死亡数か
らＴＬｍ値を算出した。結果を〔表２〕に示す。ここで
も５尾のマゴイを用い、２反復行なった。[Fish Toxicity Test] A fish toxicity test was conducted by the above-mentioned test method. The TLm value was calculated from the number of dead fish after 24, 48, 72 and 96 hours. The results are shown in [Table 2]. Again, 5 magois were used and repeated 2 times.
【００３８】[0038]
【表２】 [Table 2]
【００３９】[0039]
【実施例２５】混合機中にライトン粒９１部を入れてか
きまぜながら、あらかじめダイアジノン３部にオクチル
ジフェニルホスフェート６部を加えて均一混合したもの
を吸着させて粒剤を得る。Example 25 91 parts of Ryton granules were put in a mixer and stirred, and 3 parts of diazinon and 6 parts of octyldiphenyl phosphate were added in advance and uniformly mixed to obtain a granule.
【実施例２６】混合機中にライトン粒９１部を入れてか
きまぜながら、あらかじめダイアジノン３部にフェニル
キシリルエタン６部を加えて均一混合したものを吸着さ
せて粒剤を得る。Example 26 91 parts of Ryton particles were put in a mixer and stirred, and 3 parts of diazinon and 6 parts of phenylxylylethane were added in advance and uniformly mixed to obtain a granule.
【実施例２７】混合機中にライトン粒９１部を入れてか
きまぜながら、あらかじめマラソン３部にフェニルキシ
リルエタン６部を加えて均一混合したものを吸着させて
粒剤を得る。Example 27 91 parts of Ryton granules were put in a mixer and stirred, and 3 parts of marathon was admixed with 6 parts of phenylxylylethane in advance and admixed to obtain granules.
【実施例２８】混合機中にライトン粒９１部を入れてか
きまぜながら、あらかじめマラソン３部にオクチルジフ
ェニルホスフェート６部を加えて均一混合したものを吸
着させて粒剤を得る。Example 28 91 parts of Ryton grains are put in a mixer and stirred, and 3 parts of marathon and 6 parts of octyldiphenyl phosphate are added in advance and the mixture is uniformly adsorbed to obtain granules.
【実施例２９】混合機中にシリカ粒９６部を入れてかき
まぜながら、あらかじめマラソン２部にフタル酸ジメチ
ル２部を加えて均一混合したものを吸着させて粒剤を得
る。Example 29 96 parts of silica particles are put into a mixer and stirred, and 2 parts of dimethyl phthalate is added in advance to 2 parts of marathon and the mixture is adsorbed to obtain granules.
【実施例３０】混合機中にライトン粒９１部を入れてか
きまぜながら、あらかじめエルサン３部にフェニルキシ
リルエタン６部を加えて均一混合したものを吸着させて
粒剤を得る。Example 30 91 parts of Ryton granules were put in a mixer and stirred, and 3 parts of ersan was previously added with 6 parts of phenylxylylethane and the mixture was uniformly adsorbed to obtain granules.
【００４０】[0040]
【実施例３１】混合機中にライトン粒９７部を入れてか
きまぜながら、あらかじめエルサン１.５部にフェニル
キシリルエタン１.５部を加えて均一混合したものを吸
着させて粒剤を得る。Example 31 97 parts of Ryton granules were put into a mixer and stirred, and 1.5 parts of phenylxylylethane was added to 1.5 parts of Elsan in advance and the mixture was uniformly adsorbed to obtain granules.
【実施例３２】混合機中にライトン粒９１部を入れてか
きまぜながら、あらかじめスミチオン３部にフェニルキ
シリルエタン６部を加えて均一混合したものを吸着させ
て粒剤を得る。Example 32 91 parts of Ryton granules were put into a mixer and stirred, and 3 parts of sumithione and 6 parts of phenylxylylethane were added in advance and the mixture was uniformly adsorbed to obtain granules.
【実施例３３】混合機中にライトン粒９０部を入れてか
きまぜながら、あらかじめスミチオン５部にオクチルジ
フェニルホスフェート５部を加えて均一混合したものを
吸着させて粒剤を得る。Example 33 90 parts of Ryton grains are put in a mixer and stirred, and 5 parts of octyldiphenyl phosphate is added to 5 parts of sumithion in advance and the mixture is uniformly adsorbed to obtain granules.
【実施例３４】混合機中にライトン粒９４部を入れてか
きまぜながら、あらかじめピラクロホス３部にフタル酸
ジメチル３部を加えて均一混合したものを吸着させて粒
剤を得る。Example 34 94 parts of Ryton granules were placed in a mixer and stirred, and 3 parts of dimethyl phthalate was added in advance to 3 parts of pyraclofos and the mixture was uniformly adsorbed to obtain granules.
【実施例３５】混合機中にライトン粒９４部を入れてか
きまぜながら、あらかじめピラクロホス３部にトリ（ク
ロロエチル）ホスフェート３部を加えて均一混合したも
のを吸着させて粒剤を得る。Example 35 94 parts of Ryton granules were placed in a mixer and agitated while stirring 3 parts of tri (chloroethyl) phosphate to 3 parts of pyraclofos in advance to obtain granules.
【００４１】親油性有機リン系殺虫剤についての対照製
剤は以下に示す。Control formulations for lipophilic organophosphorus pesticides are shown below.
【対照製剤８】混合機中でダイアジノン３部をライトン
粒９７部に吸着させて粒剤を得る。[Control formulation 8] 3 parts of diazinon are adsorbed on 97 parts of Ryton grains in a mixer to obtain granules.
【対照製剤９】混合機中でマラソン３部をライトン粒９
７部に吸着させて粒剤を得る。[Control formulation 9] 3 parts of marathon in a mixer
Granules are obtained by adsorbing on 7 parts.
【対照製剤１０】混合機中でエルサン３部をライトン粒
９７部に吸着させて粒剤を得る。[Control formulation 10] 3 parts of Elsan are adsorbed on 97 parts of Ryton grains in a mixer to obtain granules.
【対照製剤１１】混合機中でスミチオン３部をライトン
粒９７部に吸着させて粒剤を得る。[Control formulation 11] 3 parts of Sumithion are adsorbed on 97 parts of Ryton grains in a mixer to obtain granules.
【対照製剤１２】混合機中でピラクロホス３部をライト
ン粒９７部に吸着させて粒剤を得る。[Control preparation 12] 3 parts of pyraclofos are adsorbed on 97 parts of Ryton granules in a mixer to obtain granules.
【００４２】[0042]
【魚毒性試験】前記した試験法で魚毒性試験を行なっ
た。２４および４８時間後の魚の死亡数からＴＬｍ値を
算出した。結果を〔表３〕に示す。なお、実施例３４，
３５の製剤および対照製剤１２に関する試験はマゴイの
かわりに５尾のドジョウ（体長９.４cm，体重５.９ｇ）
を、磁器製ポットのかわりにガラス製ビーカー（内径１
３cm，深さ１９cm）を使用し、２反復行なった。[Fish Toxicity Test] A fish toxicity test was conducted by the above-mentioned test method. The TLm value was calculated from the number of dead fish after 24 and 48 hours. The results are shown in [Table 3]. In addition, in Example 34,
The test of 35 preparations and control preparation 12 was conducted with 5 loaches (length: 9.4 cm, weight: 5.9 g) instead of macaw.
Instead of a porcelain pot, a glass beaker (inner diameter 1
3 cm, depth 19 cm) and repeated 2 times.
【００４３】[0043]
【表３】 [Table 3]
【００４４】[0044]
【実施例３６】カルタップ３部にフェニルキシリルエタ
ン６部，カオリナイトクレイ８７部，ＰＶＡ４部を加え
て均一混合し、水１６部を注加して練合したのち造粒機
で造粒し、ついで８５℃の熱風で乾燥することにより粒
剤を得る。Example 36 6 parts of phenylxylylethane, 87 parts of kaolinite clay and 4 parts of PVA were added to 3 parts of Cartap and uniformly mixed, and 16 parts of water was added and kneaded, followed by granulation with a granulator. Then, the granules are obtained by drying with hot air at 85 ° C.
【実施例３７】カルタップ３部にフェニルキシリルエタ
ン９部，カオリナイトクレイ８４部，ＰＶＡ４部を加え
て均一混合し、水１５部を注加して練合したのち造粒機
で造粒し、ついで８５℃の熱風で乾燥することにより粒
剤を得る。Example 37 9 parts of phenylxylylethane, 84 parts of kaolinite clay and 4 parts of PVA were added to 3 parts of Cartap and uniformly mixed, and 15 parts of water was added thereto and kneaded, followed by granulation with a granulator. Then, the granules are obtained by drying with hot air at 85 ° C.
【実施例３８】ルーバン３部にフェニルキシリルエタン
６部，カオリナイトクレイ８７部，ＰＶＡ４部を加えて
均一混合し、水１５部を注加して練合したのち造粒機で
造粒し、ついで７０℃の熱風で乾燥することにより粒剤
を得る。Example 38 To 3 parts of Louvain, 6 parts of phenylxylylethane, 87 parts of kaolinite clay and 4 parts of PVA were added and uniformly mixed, and 15 parts of water was added and kneaded, followed by granulation with a granulator. Then, granules are obtained by drying with hot air at 70 ° C.
【実施例３９】ルーバン３部にオクチルジフェニルホス
フェート６部，カオリナイトクレイ８７部，ＰＶＡ４部
を加えて均一混合し、水１５部を注加して練合したのち
造粒機で造粒し、ついで７０℃の熱風で乾燥することに
より粒剤を得る。[Example 39] 6 parts of octyldiphenyl phosphate, 87 parts of kaolinite clay and 4 parts of PVA were added to 3 parts of Louvain and uniformly mixed, and 15 parts of water was added thereto and kneaded, followed by granulation with a granulator, Then, the granules are obtained by drying with hot air at 70 ° C.
【００４５】カルバメート系殺虫剤についての対照製剤
は以下に示す。A control formulation for the carbamate insecticide is shown below.
【対照製剤１３】カルタップ３部にカオリナイトクレイ
９３部，ＰＶＡ４部を加えて均一混合し、水１５部を注
加して練合したのち造粒機で造粒し、ついで８５℃の熱
風で乾燥することにより粒剤を得る。[Control formulation 13] To 3 parts of cartap, 93 parts of kaolinite clay and 4 parts of PVA were added and mixed homogeneously, 15 parts of water was added and kneaded, and then granulated with a granulator, and then with hot air at 85 ° C. Granules are obtained by drying.
【対照製剤１４】ルーバン３部にカオリナイトクレイ９
３部，ＰＶＡ４部を加えて均一混合し、水１５部を注加
して練合したのち造粒機で造粒し、ついで７０℃の熱風
で乾燥することにより粒剤を得る。[Control formulation 14] Kaolinite clay 9 in 3 parts of louban
3 parts and 4 parts of PVA are added and uniformly mixed, 15 parts of water is added and kneaded, then granulated by a granulator, and then dried by hot air at 70 ° C. to obtain a granule.
【００４６】[0046]
【魚毒性試験】前記した試験法で魚毒性試験を行なっ
た。２４および４８時間後の魚の死亡数からＴＬｍ値を
算出した。結果を〔表４〕に示す。ここでも５尾のマゴ
イを用い、２反復行なった。[Fish Toxicity Test] A fish toxicity test was conducted by the above-mentioned test method. The TLm value was calculated from the number of dead fish after 24 and 48 hours. The results are shown in [Table 4]. Again, 5 magois were used and repeated 2 times.
【００４７】[0047]
【表４】 [Table 4]
【００４８】[0048]
【実施例４０】ＴＰＮ３部にフェニルキシリルエタン６
部，カオリナイトクレイ８８部，ＰＶＡ３部を加えて均
一混合し、水１３部を注加して練合したのち造粒機で造
粒し、ついで８７℃の熱風で乾燥することにより粒剤を
得る。Example 40: Phenylxylylethane 6 in 3 parts of TPN
Part, 88 parts of kaolinite clay and 3 parts of PVA are added and uniformly mixed, 13 parts of water is added and kneaded, then granulated with a granulator, and then dried with hot air at 87 ° C. to prepare granules. obtain.
【実施例４１】ＴＰＮ３部にオクチルジフェニルホスフ
ェート６部，カオリナイトクレイ８８部，ＰＶＡ３部を
加えて均一混合し、水１４部を注加して練合したのち造
粒機で造粒し、ついで９０℃の熱風で乾燥することによ
り粒剤を得る。Example 41 To 3 parts of TPN, 6 parts of octyldiphenyl phosphate, 88 parts of kaolinite clay and 3 parts of PVA were added and uniformly mixed, 14 parts of water was added and kneaded, and then granulated with a granulator, Granules are obtained by drying with hot air at 90 ° C.
【００４９】親油性殺菌剤についての対照製剤は以下に
示す。The control formulation for the lipophilic fungicide is shown below.
【対照製剤１５】ＴＰＮ３部にカオリナイトクレイ９３
部，ＰＶＡ４部を加えて均一混合し、水１４部を注加し
て練合したのち造粒機で造粒し、ついで８５℃の熱風で
乾燥することにより粒剤を得る。[Control formulation 15] Kaolinite clay 93 in 3 parts of TPN
Parts and 4 parts of PVA are added and uniformly mixed, 14 parts of water is added and kneaded, then granulated by a granulator, and then dried with hot air at 85 ° C. to obtain granules.
【魚毒性試験】前記した試験法で魚毒性試験を行なっ
た。２４および４８時間後の魚の死亡数からＴＬｍ値を
算出した。結果を〔表５〕に示す。ここでも５尾のマゴ
イを用い、２反復行なった。[Fish Toxicity Test] A fish toxicity test was conducted by the above-mentioned test method. The TLm value was calculated from the number of dead fish after 24 and 48 hours. The results are shown in [Table 5]. Again, 5 magois were used and repeated 2 times.
【００５０】[0050]
【表５】 [Table 5]
【００５１】[0051]
【発明の効果】本発明の魚毒軽減方法は、親油性農薬活
性成分を含有する農薬製剤における該農薬活性成分の魚
介類に対する毒性を軽減することができる。本発明の魚
毒軽減方法に用いる農薬製剤は、簡易かつ安価に製造す
ることができ、さらには長期間の保存後においても適確
に、しかもすぐれた作用と魚介類に対する毒性軽減の効
果を奏しうるから、本発明の魚毒軽減方法の当業界にお
ける有用性はきわめて大きいといえる。INDUSTRIAL APPLICABILITY The method for reducing fish poison of the present invention can reduce the toxicity of a pesticide active ingredient in a pesticide formulation containing a lipophilic pesticide active ingredient to fish and shellfish. The pesticide formulation used in the method for reducing fish poison of the present invention can be produced easily and inexpensively, and further, even after being stored for a long time, it exhibits an appropriate action and an effect of reducing toxicity to seafood. Therefore, it can be said that the fish poison reduction method of the present invention is extremely useful in the art.
Claims (9)
またはＣ8-24アルケニル基を、Ｒ2は直鎖状または分枝
状のＣ2-12アルキル基を示す〕で表される脂肪酸エステ
ル類〔III〕、 式 【化１】 〔式中、Ｒ3は直鎖状または分枝状のＣ2-12アルキル基
を、ｍは２〜４の整数を示す〕で表されるジエステル類
〔IV〕、 式 【化２】 〔式中、Ｒ4，Ｒ5，Ｒ6は同一または異なって直鎖状ま
たは分枝状のＣ3-12アルキル基，Ｃ1-4塩化アルキル基
またはフェニル基を示す〕で表されるリン酸エステル類
〔Ｖ〕、 式 【化３】 〔式中、Ｒ7は直鎖状または分枝状のＣ2-16アルキル
基，ｎはＲ7基が１〜４個置換していることを示す〕で
表されるアルキルベンゼン類〔VI〕、 式 【化４】 〔式中、Ｒ8，Ｒ9，Ｒ10は水素原子または直鎖状もしく
は分枝状のＣ1-3アルキル基を、ｐ，ｑはＲ8，Ｒ9基が
１〜３個置換していることを示す〕で表されるジフェニ
ルメタン類〔VII〕、 式 【化５】 〔式中、Ｒ11は直鎖状または分枝状のＣ1-12アルキル基
を示す〕で表される安息香酸エステル類〔VIII〕および 式 【化６】 〔式中、Ｒ12，Ｒ13はそれぞれ直鎖状または分枝状のＣ
1-12アルキル基を示す〕で表されるフタル酸エステル類
〔IX〕から成る群から選ばれる一種または二種以上の有
機化合物〔II〕とを含有せしめることを特徴とする該農
薬活性成分〔Ｉ〕を含有する農薬製剤の魚介類に対する
毒性を軽減する方法。1. A lipophilic pesticide active ingredient [I] and a compound represented by the formula R 1 COOR 2 [wherein R 1 represents a linear or branched C 8-24 alkyl group or a C 8-24 alkenyl group, R 2 represents a linear or branched C 2-12 alkyl group], a fatty acid ester [III] represented by the formula: [Wherein R 3 represents a linear or branched C 2-12 alkyl group, and m represents an integer of 2 to 4], and a diester [IV] represented by the formula: [Wherein R 4 , R 5 and R 6 are the same or different and each represents a linear or branched C 3-12 alkyl group, C 1-4 chloroalkyl group or phenyl group] Acid esters [V], formula: [Wherein, R 7 represents a linear or branched C 2-16 alkyl group, and n represents that 1 to 4 R 7 groups are substituted], an alkylbenzene compound [VI], Formula [In the formula, R 8 , R 9 and R 10 are hydrogen atoms or linear or branched C 1-3 alkyl groups, and p and q are substituted by 1 to 3 R 8 and R 9 groups. The diphenylmethanes [VII] represented by the formula: [In the formula, R 11 represents a linear or branched C 1-12 alkyl group] and benzoic acid esters [VIII] and a compound of the formula: [In the formula, R 12 and R 13 are each linear or branched C
1-12 alkyl group], and one or more organic compounds [II] selected from the group consisting of phthalates [IX]. A method for reducing the toxicity of an agricultural chemical formulation containing I] to seafood.
アミル，ミリスチン酸アミル，パルミチン酸ブチル，パ
ルミチン酸アミル，パルミチン酸ヘキシル，ステアリン
酸ブチル，ステアリン酸アミル，ステアリン酸ヘキシ
ル，オレイン酸ブチル，オレイン酸アミルまたはリノー
ル酸ブチルであり、 ジエステル類〔IV〕がコハク酸ジエチル，コハク酸ジ
プロピル，コハク酸ジブチル，コハク酸ジアミル，コハ
ク酸ジオクチル，グルタル酸ジエチル，グルタル酸ジブ
チル，グルタル酸ジアミル，グルタル酸ジオクチル，ア
ジピン酸ジブチル，アジピン酸ジアミルまたはアジピン
酸ジオクチルであり、 リン酸エステル類〔Ｖ〕がトリブチルホスフェート，
トリアミルホスフェート，トリオクチルホスフェート，
ブチルジフェニルホスフェート，オクチルジフェニルホ
スフェートまたはトリ（クロロエチル）ホスフェートで
あり、 アルキルベンゼン類〔VI〕がジエチルベンゼン，ジイ
ソプロピルベンゼン，トリイソプロピルベンゼン，tert
−ブチルベンゼン，ジ（tert−ブチル）ベンゼン，ジア
ミルベンゼン，トリアミルベンゼン，テトラアミルベン
ゼン，tert−アミルベンゼン，ジ（tert−アミル）ベン
ゼン，オクチルベンゼン，ドデシルベンゼンまたはジド
デシルベンゼンであり、 ジフェニルメタン類〔VII〕がフェニルキシリルエタ
ン，フェニルキシリルプロパン，トリキシリルエタン，
ジキシリルメタンまたはジイソキシリルエタンであり、 安息香酸エステル類〔VIII〕が安息香酸メチル，安息
香酸エチル，安息香酸ブチル，安息香酸アミル，安息香
酸ヘキシル，安息香酸オクチルまたは安息香酸ノニルで
あり、 フタル酸エステル類〔IX〕がフタル酸ジメチル，フタ
ル酸ジエチル，フタル酸ジブチルまたはフタル酸ジオク
チルである請求項１記載の方法。2. A fatty acid ester [III] is amyl laurate, amyl myristate, butyl palmitate, amyl palmitate, hexyl palmitate, butyl stearate, amyl stearate, hexyl stearate, butyl oleate, oleic acid. Amyl or butyl linoleate, and the diesters [IV] are diethyl succinate, dipropyl succinate, dibutyl succinate, diamyl succinate, dioctyl succinate, diethyl glutarate, dibutyl glutarate, diamyl glutarate, dioctyl glutarate, Dibutyl adipate, diamyl adipate or dioctyl adipate, wherein the phosphoric acid ester [V] is tributyl phosphate,
Triamyl phosphate, trioctyl phosphate,
Butyldiphenylphosphate, octyldiphenylphosphate or tri (chloroethyl) phosphate, alkylbenzenes [VI] being diethylbenzene, diisopropylbenzene, triisopropylbenzene, tert.
-Butylbenzene, di (tert-butyl) benzene, diamylbenzene, triamylbenzene, tetraamylbenzene, tert-amylbenzene, di (tert-amyl) benzene, octylbenzene, dodecylbenzene or didodecylbenzene, diphenylmethane Class [VII] is phenylxylylethane, phenylxylylpropane, trixylylethane,
Dixylylmethane or diisoxylylethane, benzoic acid esters [VIII] being methyl benzoate, ethyl benzoate, butyl benzoate, amyl benzoate, hexyl benzoate, octyl benzoate or nonyl benzoate, phthalate ester The method according to claim 1, wherein the class [IX] is dimethyl phthalate, diethyl phthalate, dibutyl phthalate or dioctyl phthalate.
〔VI〕である請求項１記載の方法。3. The method according to claim 1, wherein the organic compound [II] is an alkylbenzene [VI].
コハク酸ジブチル，アジピン酸ジブチル，アジピン酸ジ
オクチル，トリブチルホスフェート，トリオクチルホス
フェート，ジエチルベンゼン，tert−ブチルベンゼン，
ドデシルベンゼン，フェニルキシリルエタンまたはフタ
ル酸ジオクチルである請求項１記載の方法。4. The organic compound [II] is butyl stearate,
Dibutyl succinate, dibutyl adipate, dioctyl adipate, tributyl phosphate, trioctyl phosphate, diethylbenzene, tert-butylbenzene,
The method according to claim 1, which is dodecylbenzene, phenylxylylethane or dioctyl phthalate.
ンである請求項１記載の方法。5. The method according to claim 1, wherein the organic compound [II] is phenylxylylethane.
る請求項１〜５のいずれかに記載の方法。6. The method according to claim 1, which further comprises a carrier.
有機化合物〔II〕を０.１〜５部含有せしめることを特
徴とする請求項１記載の方法。7. A lipophilic pesticide active ingredient [I] (1 part),
The method according to claim 1, wherein 0.1 to 5 parts of the organic compound [II] is contained.
れかに記載の方法。8. The method according to claim 1, wherein the preparation is a solid preparation.
またはＣ8-24アルケニル基を、Ｒ2は直鎖状または分枝
状のＣ2-12アルキル基を示す〕で表される脂肪酸エステ
ル類〔III〕、 式 【化７】 〔式中、Ｒ3は直鎖状または分枝状のＣ2-12アルキル基
を、ｍは２〜４の整数を示す〕で表されるジエステル類
〔IV〕、 式 【化８】 〔式中、Ｒ4，Ｒ5，Ｒ6は同一または異なって直鎖状ま
たは分枝状のＣ3-12アルキル基，Ｃ1-4塩化アルキル基
またはフェニル基を示す〕で表されるリン酸エステル類
〔Ｖ〕、 式 【化９】 〔式中、Ｒ7は直鎖状または分枝状のＣ2-16アルキル
基，ｎはＲ7基が１〜４個置換していることを示す〕で
表されるアルキルベンゼン類〔VI〕、 式 【化１０】 〔式中、Ｒ8，Ｒ9，Ｒ10は水素原子または直鎖状もしく
は分枝状のＣ1-3アルキル基を、ｐ，ｑはＲ8，Ｒ9基が
１〜３個置換していることを示す〕で表されるジフェニ
ルメタン類〔VII〕、 式 【化１１】 〔式中、Ｒ11は直鎖状または分枝状のＣ1-12アルキル基
を示す〕で表される安息香酸エステル類〔VIII〕および 式 【化１２】 〔式中、Ｒ12，Ｒ13はそれぞれ直鎖状または分枝状のＣ
1-12アルキル基を示す〕で表されるフタル酸エステル類
〔IX〕から成る群から選ばれる一種または二種以上の有
機化合物〔II〕とを用いることを特徴とする該農薬活性
成分〔Ｉ〕の魚介類に対する毒性を軽減する方法。9. A lipophilic pesticide active ingredient [I] and a compound represented by the formula R 1 COOR 2 [wherein R 1 is a linear or branched C 8-24 alkyl group or a C 8-24 alkenyl group, R 2 represents a linear or branched C 2-12 alkyl group], fatty acid esters [III] represented by the formula: [Wherein R 3 represents a linear or branched C 2-12 alkyl group, and m represents an integer of 2 to 4], and a diester [IV] represented by the formula: [Wherein R 4 , R 5 and R 6 are the same or different and each represents a linear or branched C 3-12 alkyl group, C 1-4 chloroalkyl group or phenyl group] Acid esters [V], formula: [Wherein, R 7 represents a linear or branched C 2-16 alkyl group, and n represents that 1 to 4 R 7 groups are substituted], an alkylbenzene compound [VI], Formula [In the formula, R 8 , R 9 and R 10 are hydrogen atoms or linear or branched C 1-3 alkyl groups, and p and q are substituted by 1 to 3 R 8 and R 9 groups. The diphenylmethanes [VII] represented by the formula: [In the formula, R 11 represents a linear or branched C 1-12 alkyl group] and benzoic acid esters [VIII] and a compound of the formula: [In the formula, R 12 and R 13 are each linear or branched C
1-12 alkyl group] and one or more organic compounds [II] selected from the group consisting of phthalates [IX]. ] The method of reducing the toxicity to seafood.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8025002A JP2824567B2 (en) | 1985-01-24 | 1996-02-13 | How to reduce fish poison in pesticide formulations |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MC85/00027 | 1985-01-24 | ||
| PCT/JP1985/000027 WO1986004214A1 (en) | 1985-01-24 | 1985-01-24 | Agricultural chemical preparation having alleviated toxicity against fish |
| JP8025002A JP2824567B2 (en) | 1985-01-24 | 1996-02-13 | How to reduce fish poison in pesticide formulations |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61009810A Division JPH0710761B2 (en) | 1985-01-24 | 1986-01-20 | Pesticide formulation to reduce fish poison |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH08253401A true JPH08253401A (en) | 1996-10-01 |
| JP2824567B2 JP2824567B2 (en) | 1998-11-11 |
Family
ID=26362608
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8025002A Expired - Fee Related JP2824567B2 (en) | 1985-01-24 | 1996-02-13 | How to reduce fish poison in pesticide formulations |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2824567B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002525293A (en) * | 1998-09-28 | 2002-08-13 | ディクシー ケミカル カンパニー | Aliphatic carboxylic esters as non-selective herbicides |
| WO2011101966A1 (en) * | 2010-02-18 | 2011-08-25 | 全国農業協同組合連合会 | Herbicidal composition |
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| JPS5659701A (en) * | 1980-01-30 | 1981-05-23 | Nippon Nohyaku Co Ltd | Powdery agricultural chemical composition containing little dust and its preparation |
| JPS58124704A (en) * | 1982-01-16 | 1983-07-25 | Mikasa Kagaku Kogyo Kk | Granular chemical for agricultural and disinfection use |
| JPS61171402A (en) * | 1985-01-24 | 1986-08-02 | Takeda Chem Ind Ltd | Agricultural chemical preparation having reduced fish toxicity |
-
1996
- 1996-02-13 JP JP8025002A patent/JP2824567B2/en not_active Expired - Fee Related
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4934815A (en) * | 1972-07-28 | 1974-03-30 | ||
| JPS5399327A (en) * | 1977-02-04 | 1978-08-30 | Nissan Chem Ind Ltd | Pesticide preparations for water surface spreading use |
| JPS5555103A (en) * | 1978-10-20 | 1980-04-22 | Sumitomo Chem Co Ltd | Stabilizing process |
| JPS5547602A (en) * | 1978-10-25 | 1980-04-04 | Sankyo Co Ltd | Herbicide |
| JPS5659701A (en) * | 1980-01-30 | 1981-05-23 | Nippon Nohyaku Co Ltd | Powdery agricultural chemical composition containing little dust and its preparation |
| JPS58124704A (en) * | 1982-01-16 | 1983-07-25 | Mikasa Kagaku Kogyo Kk | Granular chemical for agricultural and disinfection use |
| JPS61171402A (en) * | 1985-01-24 | 1986-08-02 | Takeda Chem Ind Ltd | Agricultural chemical preparation having reduced fish toxicity |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002525293A (en) * | 1998-09-28 | 2002-08-13 | ディクシー ケミカル カンパニー | Aliphatic carboxylic esters as non-selective herbicides |
| WO2011101966A1 (en) * | 2010-02-18 | 2011-08-25 | 全国農業協同組合連合会 | Herbicidal composition |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2824567B2 (en) | 1998-11-11 |
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