GB2433030A - Emulsifiable concentrate - Google Patents
Emulsifiable concentrate Download PDFInfo
- Publication number
- GB2433030A GB2433030A GB0704016A GB0704016A GB2433030A GB 2433030 A GB2433030 A GB 2433030A GB 0704016 A GB0704016 A GB 0704016A GB 0704016 A GB0704016 A GB 0704016A GB 2433030 A GB2433030 A GB 2433030A
- Authority
- GB
- United Kingdom
- Prior art keywords
- weight
- emulsifiable concentrate
- octanoate
- diflufenican
- aromatic hydrocarbon
- 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
- 239000004495 emulsifiable concentrate Substances 0.000 title claims abstract description 243
- -1 sorbitan fatty acid ester Chemical class 0.000 claims abstract description 177
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 130
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 102
- 229930195729 fatty acid Natural products 0.000 claims abstract description 102
- 239000000194 fatty acid Substances 0.000 claims abstract description 102
- 239000004094 surface-active agent Substances 0.000 claims abstract description 72
- 239000002736 nonionic surfactant Substances 0.000 claims abstract description 50
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims abstract description 47
- 150000003839 salts Chemical class 0.000 claims abstract description 45
- 239000002253 acid Substances 0.000 claims abstract description 44
- 239000003945 anionic surfactant Substances 0.000 claims abstract description 30
- QBEXFUOWUYCXNI-UHFFFAOYSA-N Ioxynil octanoate Chemical compound CCCCCCCC(=O)OC1=C(I)C=C(C#N)C=C1I QBEXFUOWUYCXNI-UHFFFAOYSA-N 0.000 claims abstract description 8
- DQKWXTIYGWPGOO-UHFFFAOYSA-N (2,6-dibromo-4-cyanophenyl) octanoate Chemical compound CCCCCCCC(=O)OC1=C(Br)C=C(C#N)C=C1Br DQKWXTIYGWPGOO-UHFFFAOYSA-N 0.000 claims abstract description 6
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 claims description 185
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 56
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims description 45
- 238000002360 preparation method Methods 0.000 claims description 35
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 239000004359 castor oil Substances 0.000 claims description 13
- 235000019438 castor oil Nutrition 0.000 claims description 13
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 13
- 238000007865 diluting Methods 0.000 claims description 6
- 239000012141 concentrate Substances 0.000 abstract description 3
- NYQXIOZBHWFCBU-UHFFFAOYSA-N n-phenylpyridine-3-carboxamide Chemical compound C=1C=CN=CC=1C(=O)NC1=CC=CC=C1 NYQXIOZBHWFCBU-UHFFFAOYSA-N 0.000 abstract description 3
- 125000000129 anionic group Chemical group 0.000 abstract 1
- 239000005507 Diflufenican Substances 0.000 description 141
- WYEHFWKAOXOVJD-UHFFFAOYSA-N diflufenican Chemical group FC1=CC(F)=CC=C1NC(=O)C1=CC=CN=C1OC1=CC=CC(C(F)(F)F)=C1 WYEHFWKAOXOVJD-UHFFFAOYSA-N 0.000 description 141
- 239000004480 active ingredient Substances 0.000 description 89
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 86
- NRXQIUSYPAHGNM-UHFFFAOYSA-N ioxynil Chemical compound OC1=C(I)C=C(C#N)C=C1I NRXQIUSYPAHGNM-UHFFFAOYSA-N 0.000 description 84
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 description 74
- 239000005489 Bromoxynil Substances 0.000 description 74
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 60
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 57
- 150000001875 compounds Chemical class 0.000 description 54
- 239000000126 substance Substances 0.000 description 42
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 39
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 33
- 229920001451 polypropylene glycol Polymers 0.000 description 23
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 21
- 229940035044 sorbitan monolaurate Drugs 0.000 description 21
- 229920001400 block copolymer Polymers 0.000 description 19
- 239000000839 emulsion Substances 0.000 description 17
- 239000002904 solvent Substances 0.000 description 14
- 150000004996 alkyl benzenes Chemical class 0.000 description 12
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 8
- 241000219357 Cactaceae Species 0.000 description 8
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 description 6
- 229940077388 benzenesulfonate Drugs 0.000 description 6
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- 229910019142 PO4 Inorganic materials 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- 239000010452 phosphate Substances 0.000 description 5
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 4
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 4
- 150000005215 alkyl ethers Chemical class 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 230000002363 herbicidal effect Effects 0.000 description 4
- 239000001593 sorbitan monooleate Substances 0.000 description 4
- 235000011069 sorbitan monooleate Nutrition 0.000 description 4
- 229940035049 sorbitan monooleate Drugs 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000001587 sorbitan monostearate Substances 0.000 description 3
- 235000011076 sorbitan monostearate Nutrition 0.000 description 3
- 229940035048 sorbitan monostearate Drugs 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- 239000001149 (9Z,12Z)-octadeca-9,12-dienoate Substances 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 2
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 2
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 2
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical class CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 2
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 2
- UBLAMKHIFZBBSS-UHFFFAOYSA-N 3-Methylbutyl pentanoate Chemical compound CCCCC(=O)OCCC(C)C UBLAMKHIFZBBSS-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 2
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- XUPYJHCZDLZNFP-UHFFFAOYSA-N butyl butanoate Chemical compound CCCCOC(=O)CCC XUPYJHCZDLZNFP-UHFFFAOYSA-N 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- PQLMXFQTAMDXIZ-UHFFFAOYSA-N isoamyl butyrate Chemical compound CCCC(=O)OCCC(C)C PQLMXFQTAMDXIZ-UHFFFAOYSA-N 0.000 description 2
- XAOGXQMKWQFZEM-UHFFFAOYSA-N isoamyl propanoate Chemical compound CCC(=O)OCCC(C)C XAOGXQMKWQFZEM-UHFFFAOYSA-N 0.000 description 2
- YRHYCMZPEVDGFQ-UHFFFAOYSA-N methyl decanoate Chemical compound CCCCCCCCCC(=O)OC YRHYCMZPEVDGFQ-UHFFFAOYSA-N 0.000 description 2
- UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- 230000000361 pesticidal effect Effects 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- RCMHUQGSSVZPDG-UHFFFAOYSA-N phenoxybenzene;phosphoric acid Chemical compound OP(O)(O)=O.C=1C=CC=CC=1OC1=CC=CC=C1 RCMHUQGSSVZPDG-UHFFFAOYSA-N 0.000 description 2
- UOHMMEJUHBCKEE-UHFFFAOYSA-N prehnitene Chemical compound CC1=CC=C(C)C(C)=C1C UOHMMEJUHBCKEE-UHFFFAOYSA-N 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- CUNWUEBNSZSNRX-RKGWDQTMSA-N (2r,3r,4r,5s)-hexane-1,2,3,4,5,6-hexol;(z)-octadec-9-enoic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O CUNWUEBNSZSNRX-RKGWDQTMSA-N 0.000 description 1
- FIWSRSRCWYARAJ-SQOFCNSWSA-N (2r,3r,4r,5s)-hexane-1,2,3,4,5,6-hexol;(z)-octadec-9-enoic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CCCCCCCC\C=C/CCCCCCCC(O)=O FIWSRSRCWYARAJ-SQOFCNSWSA-N 0.000 description 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- WTTJVINHCBCLGX-UHFFFAOYSA-N (9trans,12cis)-methyl linoleate Natural products CCCCCC=CCC=CCCCCCCCC(=O)OC WTTJVINHCBCLGX-UHFFFAOYSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 229940084778 1,4-sorbitan Drugs 0.000 description 1
- MPCAJMNYNOGXPB-UHFFFAOYSA-N 1,5-Anhydro-mannit Natural products OCC1OCC(O)C(O)C1O MPCAJMNYNOGXPB-UHFFFAOYSA-N 0.000 description 1
- MPCAJMNYNOGXPB-SLPGGIOYSA-N 1,5-anhydro-D-glucitol Chemical compound OC[C@H]1OC[C@H](O)[C@@H](O)[C@@H]1O MPCAJMNYNOGXPB-SLPGGIOYSA-N 0.000 description 1
- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
- QFMDFTQOJHFVNR-UHFFFAOYSA-N 1-[2,2-dichloro-1-(4-ethylphenyl)ethyl]-4-ethylbenzene Chemical compound C1=CC(CC)=CC=C1C(C(Cl)Cl)C1=CC=C(CC)C=C1 QFMDFTQOJHFVNR-UHFFFAOYSA-N 0.000 description 1
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 1
- BSZXAFXFTLXUFV-UHFFFAOYSA-N 1-phenylethylbenzene Chemical compound C=1C=CC=CC=1C(C)C1=CC=CC=C1 BSZXAFXFTLXUFV-UHFFFAOYSA-N 0.000 description 1
- HFZLSTDPRQSZCQ-UHFFFAOYSA-N 1-pyrrolidin-3-ylpyrrolidine Chemical compound C1CCCN1C1CNCC1 HFZLSTDPRQSZCQ-UHFFFAOYSA-N 0.000 description 1
- DVWSXZIHSUZZKJ-UHFFFAOYSA-N 18:3n-3 Natural products CCC=CCC=CCC=CCCCCCCCC(=O)OC DVWSXZIHSUZZKJ-UHFFFAOYSA-N 0.000 description 1
- IHCCLXNEEPMSIO-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 IHCCLXNEEPMSIO-UHFFFAOYSA-N 0.000 description 1
- GXJLQJFVFMCVHG-QXMHVHEDSA-N 2-methylpropyl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(C)C GXJLQJFVFMCVHG-QXMHVHEDSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- LNJCGNRKWOHFFV-UHFFFAOYSA-N 3-(2-hydroxyethylsulfanyl)propanenitrile Chemical compound OCCSCCC#N LNJCGNRKWOHFFV-UHFFFAOYSA-N 0.000 description 1
- TVZRAEYQIKYCPH-UHFFFAOYSA-N 3-(trimethylsilyl)propane-1-sulfonic acid Chemical compound C[Si](C)(C)CCCS(O)(=O)=O TVZRAEYQIKYCPH-UHFFFAOYSA-N 0.000 description 1
- DQYSALLXMHVJAV-UHFFFAOYSA-M 3-heptyl-2-[(3-heptyl-4-methyl-1,3-thiazol-3-ium-2-yl)methylidene]-4-methyl-1,3-thiazole;iodide Chemical compound [I-].CCCCCCCN1C(C)=CS\C1=C\C1=[N+](CCCCCCC)C(C)=CS1 DQYSALLXMHVJAV-UHFFFAOYSA-M 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- PLLCCSYEGQDAIW-UHFFFAOYSA-N 5-ethyl-1,6-dimethyl-5-phenylcyclohexa-1,3-diene Chemical compound C=1C=CC=CC=1C1(CC)C=CC=C(C)C1C PLLCCSYEGQDAIW-UHFFFAOYSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- MROJXXOCABQVEF-UHFFFAOYSA-N Actarit Chemical compound CC(=O)NC1=CC=C(CC(O)=O)C=C1 MROJXXOCABQVEF-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 1
- MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- ZQISRDCJNBUVMM-YFKPBYRVSA-N L-histidinol Chemical compound OC[C@@H](N)CC1=CNC=N1 ZQISRDCJNBUVMM-YFKPBYRVSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- PKIXXJPMNDDDOS-UHFFFAOYSA-N Methyl linoleate Natural products CCCCC=CCCC=CCCCCCCCC(=O)OC PKIXXJPMNDDDOS-UHFFFAOYSA-N 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- IYFATESGLOUGBX-YVNJGZBMSA-N Sorbitan monopalmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O IYFATESGLOUGBX-YVNJGZBMSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- NCHJGQKLPRTMAO-XWVZOOPGSA-N [(2R)-2-[(2R,3R,4S)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NCHJGQKLPRTMAO-XWVZOOPGSA-N 0.000 description 1
- LWZFANDGMFTDAV-BURFUSLBSA-N [(2r)-2-[(2r,3r,4s)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O LWZFANDGMFTDAV-BURFUSLBSA-N 0.000 description 1
- FHKPLLOSJHHKNU-INIZCTEOSA-N [(3S)-3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(oxan-4-yl)methanone Chemical compound C(C)N1N=CC(=C1C)C=1N(C2=NC=NC(=C2N=1)O[C@@H]1CN(CC1)C(=O)C1CCOCC1)C FHKPLLOSJHHKNU-INIZCTEOSA-N 0.000 description 1
- 229950003218 actarit Drugs 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000005418 aryl aryl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 1
- HZHMMLIMOUNKCK-UHFFFAOYSA-N dipropyl oxalate Chemical compound CCCOC(=O)C(=O)OCCC HZHMMLIMOUNKCK-UHFFFAOYSA-N 0.000 description 1
- LWIWFCDNJNZEKB-UHFFFAOYSA-N dipropyl propanedioate Chemical compound CCCOC(=O)CC(=O)OCCC LWIWFCDNJNZEKB-UHFFFAOYSA-N 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000008233 hard water Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- YAQXGBBDJYBXKL-UHFFFAOYSA-N iron(2+);1,10-phenanthroline;dicyanide Chemical compound [Fe+2].N#[C-].N#[C-].C1=CN=C2C3=NC=CC=C3C=CC2=C1.C1=CN=C2C3=NC=CC=C3C=CC2=C1 YAQXGBBDJYBXKL-UHFFFAOYSA-N 0.000 description 1
- 229940094941 isoamyl butyrate Drugs 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- DVWSXZIHSUZZKJ-YSTUJMKBSA-N methyl linolenate Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(=O)OC DVWSXZIHSUZZKJ-YSTUJMKBSA-N 0.000 description 1
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 1
- 229940073769 methyl oleate Drugs 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 239000003090 pesticide formulation Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920000090 poly(aryl ether) Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000008234 soft water Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 235000011067 sorbitan monolaureate Nutrition 0.000 description 1
- 235000011071 sorbitan monopalmitate Nutrition 0.000 description 1
- 239000001570 sorbitan monopalmitate Substances 0.000 description 1
- 229940031953 sorbitan monopalmitate Drugs 0.000 description 1
- 229960005078 sorbitan sesquioleate Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
- A01N37/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
An emulsifiable concentrate comprising: 2',4'-difluoro-2-(a,a,a-trifluoro-m-tolyloxy)nicotinanilide; 1,3-dimethy1-2-imidazolidinone; an aromatic hydrocarbon: and a surfactant. The surfactant comprises an anionic and a nonionic surfactant. The anionic surfactant is an alkylbenzenesulfonic acid salt. The nonionic surfactant may have a polyethylene oxide structure in the molecule. The nonionic surfactant may be sorbitan fatty acid ester. The concentrate may further contain 4-cyano-2,6-dibromophenyl octanoate and 4-cyano-2,6-diiodophenyl octanoate.
Description
<p>EMULSIFIABLE CONCENTIDrnt'</p>
<p>FIELD OF THE INVENTION</p>
<p>The present invention relates to a pest icidal emulsifiable concentrate which contains 2' ,4'-difluoro-2-(a,a,a-trifluorO-m-tOlylOXy)niCOtinaflilide as a herbicidal active ingredient.</p>
<p>BACKGROUND ART</p>
<p>It is known that 2' ,4'_difluoro-2-(a,a,a-trifluoro-m-tolylOXY)flicotiflaflilide shown by the below formula is an active ingredient of herbicide in USP-4618366. ((CF3 LrJ</p>
<p>DISCLOSURE OF THE INVENTION</p>
<p>The present invention provides an emulsifiable concentrate containing 2' ,4'-difluoro-2-(a,a,a-trifluoro-Tfl-tOlylOXy)niCOtiflaflilide as aherbicidal active ingredient which has an excellent stability of the emulsion even after diluted with water.</p>
<p>According to the present invention, an emulsifiable concentrate containing 2' ,4'-difluoro-2--(a,a,a-triflUOrO-m-tOlylOXY)fliCOtiflaflilide, the compound shown by the formula (1): R1((R2 (1) wherein, in the formula, R1 and R2 represent alkyl groups, A represents a single bond or an alkylene group, and the sum of the number of carbon atoms which consist of the groups of R', R2 and A is 2 to 8; and a surf actarit has an excellent stability of the emulsion even after diluted with water.</p>
<p>Namely, the present invention is as follows: [1] An emulsifiable concentrate, which is characterized by comprising 2' the compound shown by the below formula (1): R1'('jf'R2 (1) wherein, in the formula, R1 and R2 represent alkyl groups, A represents a single bond or an alkylene group, and the sum of the number of carbon atoms which consist of the groups of R', R2 and A is 2 to 8; and a surfactant.</p>
<p>[2] An emulsifiable concentrate, which is characterized by comprising 0.5 to 5 % by weight of 2' to 80 % by weight of the compound shown by the below formula (1): ) 3 R((R2 (1) wherein, in the formula, R1 and R2 represent alkyl groups, A represents a single bond or an alkylene group, and the sum of the number of carbon atoms which consist of the groups of R', R2 and A is 2 to 8; and 4 to 20 % by weight of a surfactant.</p>
<p>[3] The emulsifiable concentrate according to [1] or [2], wherein the compound shown by the formula (1) is diethyl oxalate.</p>
<p>[41 The emulsifiable concentrate according to any one of [1] to [3], wherein the ratio of the compound shown by the formula (1) is 5 to 80 by weight for one weight of 2' ,4'-difluoro-2-(a,a,a-trifluoro-rn-tOlylOXY)fliCotiflaflilide.</p>
<p>[5] The emulsifiable concentrate according to any one of [1] to [4], wherein the emulsifiable concentrate comprises an aromatic hydrocarbon.</p>
<p>[6] The emulsifiable concentrate according to any one of [1] to [4], wherein the emulsifiable concentrate comprises 1 to 40 % by weight of an aromatic hydrocarbon.</p>
<p>[7] The emulsifiable concentrate according to any one of [1] to [6], wherein the emulsifiable concentrate comprises 1, 3-dimethyl-2-imidazolidiflOne.</p>
<p>[8] The emulsifiable concentrate according to any one of [1] to [6], wherein the emulsifiable concentrate comprises 5 to 60 by weight of 1,3-dimethyl-2-imidaZolidiflOfle.</p>
<p>[9) The emulsifiable concentrate according to any one of [1] to (8], wherein the surfactant is an anionic surfactant -4 and a nonionic surfactant; and the ratio by weight of the anionic surfactant and the nonionic surfactant is 1:0.1 to 1:10.</p>
<p>[10] The emulsifiable concentrate according to [9], wherein the anionic surfactant is an alkylbenzenesulfoniC acid salt.</p>
<p>[11] The emulsifiable concentrate according to [9] or [10], wherein the nonionic surfactant is the nonionic surfactant which has polyalkylene oxide structure in the molecule.</p>
<p>[12] The emulsifiable concentrate according to [11], wherein the nonionic surfactant which has polyalkylene oxide structure in the molecule is the surfactant selected from the group consisting of polyoxyethylene-polyoxyproPYlefle tristyryl phenyl ether, polyoxyethylene tristyryl phenyl ether and polyoxyethylene castor oil.</p>
<p>[13] The emulsifiable concentrate according to [9] or [10], wherein the nonionic surfactant is a sorbitan fatty acid ester.</p>
<p>[14] The emulsifiable concentrate according to [1], wherein the emulsifiable concentrate comprises 4-cyano-2, 6-dibromophenyl octanoate and 4-cyano-2, 6-diiodophenyl octanoate.</p>
<p>[15] The emulsifiable concentrate according to [2], wherein the emulsifiable concentrate comprises 1 to 30 % by weight of 4-cyano-2,6-dibrOrflOPheflYl octanoate and 1 to 30 % by weight of 4-cyano-2,6-diiodophenyl octanoate.</p>
<p>[16] The emulsifiable concentrate according to (14] or [15], wherein the ratio of the compound shown by the formula (1) is 5 to 80 by weight for the weight of 2' ,4'_dif1uoro2-(a,a,a-trifluOrO-m-tOlYlOXY)niCOtinaflh1ide.</p>
<p>[17] The emulsifiable concentrate according to any one of [14] to [16], wherein the surfactant is an anionic surfactant and a nonionic surfactant; and the ratio by weight of the anionic surfactant and the nonionic surfactant is 1:0.1 to 1:10.</p>
<p>[18] The emulsifiable concentrate according to any one of [11] to [14], wherein the compound shown by the formula (1) is diethyl oxalate.</p>
<p>[19] The emulsifiable concentrate according to any one of [14] to [18], wherein the emulsifiable concentrate comprises an aromatic hydrocarbon.</p>
<p>[20] The emulsifiable concentrate, which is characterized by comprising 2' ,4'-difluoro-2-(a,a,a-trifluoro--m-tolylOXy)fliCOtiflaflhlide; 1,3-dirnethyl-2-imidazolidinofle; an aromatic hydrocarbon; and a surfactant.</p>
<p>[21] The emulsifiable concentrate, which is characterized by comprising 1 to 5 % by weight of 2' ,4'_dif1uoro_2(a,a,a-trifluOrO-m--tO1ylOXy)fliCOtiflafli1ide; to 60 % by weight of 1,3-dimethyl-2-imidazolidinone; to 50 % by weight of an aromatic hydrocarbon; and 4 to 20 % by weight of a surfactant.</p>
<p>[22] The emulsifiable concentrate, which is characterized by comprising 2t,4'_difluoro_2-(a,a,a-trifluorO-rfl-tOlyloXy)flicOtiflanilide; a sorbitan fatty acid ester; an anionic surfactant; and an aromatic hydrocarbon.</p>
<p>[23] The emulsifiable concentrate, which is characterized by comprising 0.5 to 5 % by weight of 2' ,4' -difluoro-2-(a,a,a-trifluoro-m-tolyloxy)nicotinanilide; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 10 % by weight of an anionic surfactant; and to 90 % by weight of an aromatic hydrocarbon.</p>
<p>[24] An aqueous composition which is obtainable by diluting the emulsifiable concentrate according to any one of [1] to [23] with water.</p>
<p>The emulsifiable concentrate of the present invention contains 2' , 4' -difluoro-2-(a,a,a-trifluoro-m-tolylOXy)fliCotinaflilide as a herbicidal active ingredient. The common name of 2' ,4' -difluoro-2-(a,a,a-trifluoro-m-tolyloxy)nicotinanilide is diflufenican(ref erred as diflufenican, hereinafter).</p>
<p>The emulsifiable concentrate of the present invention may further contain another herbicidal active compound such as 4-cyano-2, 6-dibromophenyl octanoate and 4 -cyano-2,6 -diiodophenyl octanoate.</p>
<p>4-cyano-2,6-dibromophenyl octanoate is the compound named bromoxynil octanoate as common nazne(referred as bromoxynil=octanoate, hereinafter). 4-cyano-2. 6-diiodophenyl octanoate is the compound named ioxynil octanoate as common name(referred as ioxynil=octanoate, hereinafter).</p>
<p>Diflufenican is the compound disclosed in "The Pesticide ) 7 Manual" (by British Crop Protection Council, Thirteenth Edition) as reference number 251. It is a solid compound and its melting point is about 159 to 161 C. It can be produced by the method disclosed 1nUSP-4618366. Brornoxynil=octanoate is the compound disclosed in "The PesticideManual" (mentioned above) as reference number 95. It is a solid compound and its melting point is about to 46 CC. It can be produced by the method disclosed in USP-3397054. Ioxynil=octanoate is the compound disclosed in "The Pesticide Manual" (mentioned above) as reference number 467.</p>
<p>It is a solid compound and its melting point is about 56 to 57 C. It can be produced by the method disclosed in USP-3397054.</p>
<p>In the emulsifiable concentrate of the present invention, the amount of diflufenican is usually 0.5 to 5 % by weight, preferably 1 to 5 % by weight, more preferably 1 to 4 % by weight and far more preferably 1.5 to 4 % by weight based on the total weight of the emulsifiable concentrate of the present invention.</p>
<p>In case of the emulsifiable concentrate of the present invention contains bromoxynhl=octanoate and/or ioxynhl=octanoate, the amount of bromoxynil=octanoate is usually ito 30 %byweight, preferably6 to2O %byweight andmorepreferably 8 to 18 % by weight; and the amount of ioxynil=octanoate is usually 1 to3O %byweight,preferably 4 to 12 %byweight andmore preferably 4 to 10 % by weight based on the total weight of the emulsifiable concentrate of the present invention. In this case, the total weight of diflufenican, bromoxynil=octanoate and ioxynil=octanoate is usually 1 to 60 % by weight, preferably 3 to 40 % by weight based on the total weight of the emulsifiable concentrate of the present invention.</p>
<p>The emulsifiable concentrate of the present invention contains the compound shown by the formula (1) as a solvent. The compound shown by the formula (1) can solve diflufenican.</p>
<p>Furthermore, the compound shown by the formula (1)(referred as the present solvent, hereinafter) is miscible with an organic solvent which is usually used for pesticidal formulation.</p>
<p>In the formula (1) , A represents a single bond or an alkylene group, and examples of alkylene group include methylene group, ethylene group, propylene group and trimethylene group. In the formula (1), each of R' and R2 independently represents alkyl group, and examples of alkyl group include methyl group, ethyl group, isopropyl group, butyl group. The sum of the number of carbon atoms which consist of the group of R', R2 and A in the formula (1) is 2 to 8, preferably 2 to 5.</p>
<p>Examples of the present solvent include diethyl oxalate, dipropyl oxalate, dimethylmalonate, dipropylmalonate, dimethyl succinate, diethyl succinate. The present solvent can be used for the emulsifiable concentrate of the present invention by itself or mixture of above mentioned compound. For the emulsifiable concentrate of the present invention, diethyl oxalate is preferably used.</p>
<p>The amount of the present solvent to be used for the emulsifiable concentrate of the present invention is usually 5 to 80 %byweight, preferably 20 to 80 %byweight andmore preferably to 70 % by weight based on the total weight of the emulsifiable concentrate of the present invention. And the amount of the present solvent to be used for the emulsifiable concentrate of the present invention) is usually 5 to 80 by weight, preferably ) 9 8 to 80 by weight and more preferably 8 to 30 by weight based on the weight of diflufenican.</p>
<p>The emulsifiable concentrate of the present invention may contain another organic solvent.</p>
<p>Examples of another organic solvent includes aromatic hydrocarbons such as alkylbenzene(for example, xylene, tetramethylbenzene and the like), alkylnaphthalene(for example, methylnaphthalene), diphenylethane, dixylylethane, phenyixylylethane and the like; fatty acid monoesters such as methyl laurate, isopropyl myristate, isopropyl palmitate, methyl caprate, methyl oleate, isobutyl oleate, butyl propionate, isoamyl propionate, ethyl butyrate, butyl butyrate, isoamyl butyrate, isoamyl valerate, arnyl lactate, methyl linoleate, methyl linolenate, palm fatty acid methyl and the like; aliphatic hydrocarbons such as cyclohexane; N,N-dimethyl acetamide; N-methyl-2-pyrrolidone and 1, 3-dimethyl-2-imidazolidinone.</p>
<p>Commercially available products such as Hisol SAS-296 (commercial name of Nippon Oil Corp., a mixture of 1-phenyl-1-xylylethane and 1-phenyl-1-ethyiphenylethane), Cactus Solvent HP-MN (commercial name of Nikko Petrochemical Company, containing 80% of methylnaphthalene), Cactus Solvent HP-DMN (commercial name of Nikko Petrochemical Company, containing 80% of diniethylnaphthalene), Cactus Solvent P-100 (commercial name of Nikko Petrochemical Company, alkylbenzene having 9 to 10 carbon atoms), Cactus Solvent P-iSO (commercial name of Nikko Petrochemical Company, alkylbenzene), Cactus Solvent P-laO (commercial name of Nikko Petrochemical Company, a mixture of methylnaphthalene and dimethylnaphthalene), Cactus Solvent P-200 (commercial name of Nikko Petrochemical Company, a mixture of methylnaphthalene and dimethylnaphthalene), Cactus Solvent P-220 (commercial name of Nikko Petrochemical Company, a mixture of methylnaphthalene and dimethylnaphthalene), Cactus Solvent PAD-i (commercial name of Nikko Petrochemical Company, dimethylmonoisopropylflaPhthalefle), Solves so 100 (commercial nameofExxonMobilChemical Company, aromatichydrocarbon, mainly C9 to ClO dialkyl and trialkyl benzene), Solvesso 150 (commercial name of Exxon Mobil Chemical Company, aromatic hydrocarbon. mainly ClO to Cli alkylbenzene), Solvesso 150 ND (commercial name of Exxon Mobil Chemical Company, aromatic hydrocarbon, mainly ClO to Cii alkylbenzene), Solvesso 200 (commercial name of Exxon Mobil Chemical Company, aromatic hydrocarbon, mainly ClO to C14 alkylnaphthalene), ULTRA LOW NAPHTHALENE AROMATIC 150 (commercial name of Exxon Mobil Chemical Company, aromatic hydrocarbon, mainly ClO to Cli alkylbenzene), ULTRA LOW NAPHTHALENE AROMATIC 200 (commercial name of Exxon Mobil Chemical Company, aromatic hydrocarbon, mainly Cli to C14 alkylnaphthalene), Solvesso 200 ND (commercial name of Exxon Mobil Chemical Company, aromatic hydrocarbon, mainly Cii to C14 alkylnaphthalefl), Suwasol 100 (commercial name of Maruzen Petrochemical Company, toluene) and Suwasol 200 (commercial name of Maruzen Petrochemical Company, xylene) can be used as the aromatic hydrocarbons.</p>
<p>In the emulsifiable concentrate of the present invention, it is preferable that an aromatic hydrocarbon and/or N-methyl-2-pyrrolidone and/or 1, 3-dimethyl-2-imidazolidinone are contained.</p>
<p>In case of the emulsifiable concentrate of the present invention includes an aromatic hydrocarbon, the amount of the aromatic hydrocarbon is usually 1 to 40 % by weight based on the total weight of the emulsifiable concentrate of the present invention.</p>
<p>In case of the emulsifiable concentrate of the present invention includes N-methyl-2-pyrrolidone, the amount of N-methyl-2-pyrrolidone is usually 3 to 30 % by weight based on the total weight of the emulsifiable concentrate of the present invention.</p>
<p>In case of the emulsifiable concentrate of the present invention includes 1, 3-dimethyl-2-imidazolidinone, the amount of 1,3-dimethyl-2-imidazolidinone is usually 5 to 80 % by weight, preferably 5 to 60 % by weight, more preferably 5 to 50 % by weight, far more preferably 10 to 50 % by weight based on the total weight of the emulsifiable concentrate of the present invention.</p>
<p>The emulsifiable concentrate of the present invention contains a surf actant. The surf actant used for the emulsifiable concentrate of the present invention is preferably a mixture of an anionic surfactant and a nonionic surfactant.</p>
<p>Examples of anionic surfactant include alkyl aryl sulfonic acid salt such as dodecyl benzene sulfonic acid salt and the like, polyoxyethylene(poly)arylarYl ether sulfates such as polyoxyethyJ-ene distyryl phenyl ether sulfate and the like, polyoxyethylene(poly)arylaryl ether phosphate such as polyoxyethylene tristyryl phenyl ether phosphate and the like, polyoxyethylenealkylaryl phosphate ester, and polyoxyethyleriealkyl phosphate ester.</p>
<p>Preferably alkyl aryl sulfonic acid salt such as alkyl benzene sulfonic acid salt, especially dodecy]. benzene sulfonic acid salt such as sodium salt and calcium salt is used.</p>
<p>Generally, sodium salt, calcium salt and ammonium salt are exemplified as sulfonic acid salt, sulfate salt or phosphate salt.</p>
<p>Commercially available surfactant such as Rhodacal 70, Rhodacal7o/B, Rhodacal6OfBE(each produced by Rhodia Nicca), Witconate P-1220EH(produced by Akzo Nobel) and NANSA EVM62/H(produced by Huntsman) can be used as dodecyl benzene sulfonic acid salt. Commercially available surfactant such as Soprophor DSS/11(produced by Rhodia Nicca) can be used as polyoxyethylene distyryl phenyl ether sulfate. Commercially available surfactant such as Soprophor FLK(produced by Rhodia Nicca) can be used as polyoxyethylene tristiryl phenyl ether phosphoric acid. Commercially available surfactant such as Rhodafac PS/17(produced by Rhodia Nicca) can be used as polyoxyethylenealkylaryl phosphate ester. Commercially available surf actant such as RhodafacMB(producedbyRhodiaNicca) can be used as polyoxyethylenealkyl phosphate ester.</p>
<p>Examples of nonionic surfactant include polyoxyethylene-polyoxypropylene block polymer; fatty acid ester of polyoxyethylene-polyoxypropylene block polymer; polyoxyethylene-polyoxypropylene alkyl ether; polyoxyethylene-polyoxypropylene polyary]. ether such as polyoxyethylene-polyoxypropylene tristyryl phenyl ether, polyoxyethylene-polyoxypropylene distyry]. phenyl ether and the like; polyoxyethylene-polyoxypropylene alkyl aryl ether; polyoxyethylene alkyl aryl ether; polyoxyethylene polyaryl ether such as polyoxyethylene tristyryl phenyl ether, polyoxyethylen distyryl phenyl ether and the like; polyoxyethylene vegetable oil such as polyoxyethylene castor oil and the like; polyoxyethylene hardened vegetable oil such as polyoxyethylene hardened castor oil and the like; polyoxyethylene-polyoxypropylene vegetable oil such as polyoxyethylene-polyoxypropylene castor oil and the like; polyoxyethylene fatty acid esters; polyoxyethylene alkyl ether; polyoxyethylene tristyryl phenyl phosphate diester; polyoxyethylene-polyoxypropylene tristyryl phenyl phosphate diester; polyalkyleneoxide block copolymer; butyl polyalkyleneoxide block copolymer; fatty acid alcohol polyglycol ether; fatty acid ester of glycerin; and sorbitan fatty acid ester.</p>
<p>Preferable examples of the nonionic surf actants to be used for the emulsifiable concentrate of the present invention are the nonionic surfactant which has polyalkylene oxide structure in the molecule and sorbitan fatty acid ester.</p>
<p>Examples of the nonionic surf actant which has polyalkylene oxide structure in the molecule are as polyoxyethylene-polyoxypropylene tristyryl phenyl ether, polyoxysthylene tristyryl phenyl ether, polyoxyethylene castor oil, polyoxyethylene hardened castor oil, polyoxyethylene alkyl aryl ether, polyoxyethylene tristyryl phenyl phosphate diester or polyoxyethylene-polyoxypropylene tristyryl phenyl phosphate diester.</p>
<p>In the nonionic surfactant which has polyalkylene oxide structure in the molecule, especially polyoxyethylene -polyoxypropylene tristyryl phenyl ether, polyoxypropylene tristyryl phenyl ether, polyalkyleneoxide block copolymer, butyl polyalkyleneoxide block copolymer or polyoxyethylene castor oil is preferably used for the emulsifiable concentrate of the present invention.</p>
<p>The HLB value of the nonionic surfactant which has polyalkylene oxide in the molecule is usually 10 to 17, preferably to 14, more preferably 11 to 12.</p>
<p>Commercially available surfactant such as Teric PE 64(produced by Huntsman) can be used as polyoxyethylene-polyoxypropylene block polymer. Commercially available surfactant such as Antarox BO/327, 340 Antarox BO series(each produced by Rhodia Nicca) can be used as polyoxyethylene-polyoxypropylene alkyl ether. Commercially available surfactant such as SolpolT26(producedbyToho Chemical Industry) can be used as polyoxyethylene alkyl aryl ether.</p>
<p>Commercially available surfactant such as Soprophor 796/P(HLB 13.7. produced by Rhodia Nicca) can be used as polyoxyethylene -polyoxypropylene tristyryl phenyl ether.</p>
<p>Commercially available surfactant such as SoprophorBSU(HLB 12.6, produced by RhodiaNicca) can be used as polyoxyethylene tristyryl phenyl ether. Commercially available surfactant such as Alkamuls 0R40, Alkaxnuls BR(each produced by Rhodia Nicca) can be used as polyoxyethylene castor oil. Commercially available surfactant such as HCO-20(produced by Nikko Chemicals) can be used as polyoxyethylene hardened castor oil. Commercially available surfactant such as CR series such as Antarox CR/255, CR1405 and the like(each produced by Rhodia Nicca) can be used as polyoxyethylene-polyoxypropylene castor oil. Commercially available surfactant such as Newcol 150(procluced by Nippon Nyukazai) can be used as polyoxyethylene fatty acid ester.</p>
<p>Conunercially available surfactant such as Newcol 1100, Newcol 1105(each produced by Nippon Nyukazai) can be used as polyoxyethylene alkyl aryl ester. Commercially available surfactant such as PIONIN D-900 series(produced by TAKEMOTO Oil &Fat) can be used as fatty acid ester of glycerin. Commercially available surfactant such as Toximul 8320(produced by Stepan) can be used as butyl polyalkyleneoxide block copolymer.</p>
<p>Commercially available surfactant such as Toximul 8323(produced by Stepan), Step-Flow 26(produced by Stepan) and Ethylan NS 500 LQ(produced by Akzo Nobel) can be used as polyalkyleneoxide block copolymer.</p>
<p>Sorbitan fatty acid esters are an ester compound which is condensed by sorbitan and fatty acid. Sorbitan is an intramolecular dehydration product of sorbitol. There are several kinds of sorbitan fatty acid ester such as sorbitan mono fatty acid ester, sorbitan tn fatty acid ester and the like depending on the number of condensed fatty acid. There are several kinds of sorbitans such as 1,4-sorbitan, 1,5-sorbitan and the like, depending on the dehydrating position of intramolecular dehydration of sorbitol. As fatty acids condensed with sorbitan, fatty acids which the number of carbon atoms Is 10 to 22 are usually used. Concretely, saturated fatty acids such as capric acid, lauric acid, myristic acid, pentadecanoic acid, palmitic acid, stearic acid and the like, and unsaturated fatty acids such as oleic acid, linoleic acid, linolenic acid and the like are exemplified.</p>
<p>Sorbitan fatty acid esters concretely include, for example, sórbitan mono laurate, sorbitan mono palmitate, sorbitan mono stearate, sorbitan mono oleate and the like.</p>
<p>Commercially available surfactant such as Alkamuls S20(sorbitan mono laurate, HLB 8.6, produced by Rhodia Nicca), Alkamuls S80(sorbitan mono oleate, HLB 4.3, produced by Rhodia Nicca), Glycomul S(sorbitan mono stearate, HLB 5, produced by Lonza Japan), Glycomul TS(sorbitan tn stearate, HLB 2, produced by Lonza Japan), NIKKOL SL-10(sorbitan mono laurate, HLB 8.6, produced by Nikko Chemicals), NIKKOL SP-1OV(sorbitari mono palmitate, HLB 6.7, produced by Nikko Chemicals), NIKKOL SS-1OV(sorbitan mono stearate, HLB 4.7, produced by Nikko Chemicals), NIKKOL SS-30V(sorbitan tn stearate, HLB 2.1, produced by Nikko Chemicals), NIKKOL SI-1ORV(sorbitan mono isostearate, HLB 5.0, produced by Nikko Chemicals), NIKKOL SO-15R(sorbitan sesquioleate and HLB 4.5, produced by Nikko Chemicals) can be used for the emulsifiable concentrate of the present invention.</p>
<p>In case of the emulsifiable concentrate of the present invention includes sorbitan fatty acid ester, the amount of the sorbitan fatty acid ester is usually 0.5 to 10 % by weight, preferably 1 to 8 % by weight based on the total of the emulsifiable concentrateofthepresent invention. Andinthis case, theamount of the sorbitan fatty acid ester is preferably 0.2 to 2.5 times by weight based on the weight of diflufenican. In the view point of stability while keeping in low temperature, it is preferable that the emulsifiable concentrate of the present invention includes sorbitan fatty acid ester as a nonionic surfactant. The stability while keeping in low temperature means having a character of producing little oil like separation or solid while keeping in law temperature such as below 5 DC.</p>
<p>The nonionic surfactant used for the emulsifiable concentrate of the present invention may be consisted of one kind of nonionic surfactant or may be consisted of at least two kinds of nonionic surf actants. In case of the nonionic surfactant used for the emulsifiable concentrate of the present invention is consisted of at least two kinds of nonionic surfactants, the combination of the nonionic surfactants includes, for example, the combination of the nonionic surfactant which has polyalkylene oxide structure in the molecule and sorbitan fatty acid ester, more concretely the combination of polyoxyethylene tristyryl phenyl ether and sorbitan fatty acid ester.</p>
<p>In the emulsifiable concentrate of the present invention, the amount of surfactant is usually 4 to 20 % by weight, preferably 4 to 15 % by weight based on the total weight of the emulsifiable concentrate of the present invention. In case of the surfactant used for the emulsifiable concentrate of the preset invention is a mixture of an anionic surfactant and a nonionic surf actant, the weight ratio of the anionic surfactant and the nonionic surfactant is usually 1:0.1 to 1:10, preferably 1:0.4 to 1:2.5. S 18</p>
<p>The emulsifiable concentrate of the present invention may further include an additive.</p>
<p>Examples of the additive include antioxidant such as 3-/2-t-butyl-4-hydroxyanisOle, butyl hydroxy toluene and the like; coloring agent and the like.</p>
<p>The mode of the emulsifiable concentrate of the present invention includes as following: An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 10 % by weight of an alkylbenzenesulfoniC acid salt; to 20 % by weight of an aromatic hydrocarbon; and to 70 % by weight of the compound shown by the formula (1).</p>
<p>An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 15% byweight of anonionic surf actant which has polyalkylene oxide structure in the molecule; 0.5 to 10 % by weight of an alkylbenzenesulfoniC acid salt; to 20 % by weight of an aromatic hydrocarbon; and to 70 % by weight of the compound shown by the formula (1).</p>
<p>An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of N-methyl-2-pyrrolidone; to 20 % by weight of an aromatic hydrocarbon; and to 70 % by weight of diethyl oxalate.</p>
<p>An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 0.5 to 10.% by weight of a sorbitan fatty acid ester; 0. 5 to 15% byweight of anonionic surf actant which has polyalkylene oxide structure in the molecule; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of N-methyl-2-pyrrolidone; to 20 % by weight of an aromatic hydrocarbon; and to 70 % by weight of diethyl oxalate.</p>
<p>An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of N,N-dimethylacetamide; to 20 % by weight of an aromatic hydrocarbon; and 5 to 70 % by weight of diethyl oxalate.</p>
<p>An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 15 %byweightofanonionicsurfactantwhichhaspolyalkylene oxide structure in the molecule; 0.5 to 10 % by weight of an alkylbenzeriesulfonic acid salt; 3 to 30 % by weight of N,N-dimethylacetamide; to 20 % by weight of an aromatic hydrocarbon; and to 70 % by weight of diethyl oxalate.</p>
<p>An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weightof 1,3-dimethyl-2-irnidazolidinone; to 20 % by weight of an aromatic hydrocarbon; and to 70 % by weight of diethyl oxalate.</p>
<p>An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 15% byweight of anonionic surf actant which has polyalkylene oxide structure in the molecule; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of 1,3-dimethyl-2-imidazolidinone; to 20 % by weight of an aromatic hydrocarbon; and to 70 % by weight of diethyl oxalate.</p>
<p>An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of N-methyl-2-pyrrolidone; to 20 % by weight of an aromatic hydrocarbon; and to 70 % by weight of diethyl oxalate; and the ratio by weight of diflufenican and the sorbitan fatty acid ester is 1 0.2 to 1: 1.5; and and the ratio by weight of N-methyl-2-pyrrolidone and diethyl oxalate is 1 0.1 to 1 1.</p>
<p>An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of N,N-dimethylacetalTlide; to 20 % by weight of an aromatic hydrocarbon; and 5 to 70 % by weight of diethyl oxalate; and the ratio by weight of diflufenican and the sorbitan fatty acid ester is 1: 0.2 to 1: 1.5; and and the ratio by weight of N,N-dimethylacetamide and diethyl oxalate is 1: 0.1 to 1: 1.</p>
<p>An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 15% byweight of anonionic surf actant which has polyalkylene oxide structure in the molecule; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of N,N-dimethylacetarnide; to 20 % by weight of an aromatic hydrocarbon; and to 70 % by weight of diethyl oxalate; and the ratio by weight of diflufenican and the sorbitan fatty acid ester is 1: 0.2 to 1: 1.5; and and the ratio by weight of N,N-dimethylacetamide and diethyl oxalate is 1: 0.1 to 1 1.</p>
<p>An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 10 by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of 1,3-dimethyl-2-irnidazolidinone; to 20 % by weight of an aromatic hydrocarbon; and to 70 % by weight of diethyl oxalate; and the ratio by weight of diflufenican and the sorbitan fatty acid ester is 1: 0.2 to 1: 1.5; and and the ratio by weight of 1,3-dimethyl-2-imidazolidinone and sum of an aromatic hydrocarbon and diethyl oxalate is 1 0.1 to 1 1.</p>
<p>An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0. 5 to 15 % byweight of anonionic surf actant whichhas polyalkylene oxide structure in the molecule; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of 1,3-dimethyl-2-imidazolidinone; to 20 % by weight of an aromatic hydrocarbon; and to 70 % by weight of diethyl oxalate; and the ratio by weight of diflufenican and the sorbitan fatty acid ester is 1: 0.2 to 1 1.5; and and the ratio by weight of the 1,3-dimethyl-2-imidazolidjnone and sum of an aromatic hydrocarbon and diethyl oxalate is 1 0.1 to 1: 1.</p>
<p>An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; to 20 % by weight of an aromatic hydrocarbon; and to 70 % by weight of the compound shown by the formula (1).</p>
<p>An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 15% byweightofanonionicsurfactafltWhichhaSpOlyalkylefle oxide structure in the molecule; 0.5 to 10 % by weight of an alkylbenzenesulfoniC acid salt; to 20 % by weight of an aromatic hydrocarbon; and to 70 % by weight of the compound shown by the formula (1).</p>
<p>An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of brornoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of N-methyl-2-pyrrolidone; to 20 % by weight of an aromatic hydrocarbon; and to 70 % by weight of diethyl oxalate. * 24</p>
<p>An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynhl=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 15% byweight of anonionic surfactantwhichhas polyalkylene oxide structure in the molecule; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of N-methyl-2-pyrrolidone; 5 to 20 % by weight of an aromatic hydrocarbon; and to 70 % by weight of diethyl oxalate.</p>
<p>An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of N,N-dirnethylacetamide; 5 to 20 % by weight of an aromatic hydrocarbon; and to 70 % by weight of diethyl oxalate.</p>
<p>An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 15 % byweight of a nonionic surf actant which has polyalkylene oxide structure in the molecule; 1 25 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of N,N-dimethylacetarnide; to 20 % by weight of an aromatic hydrocarbon; and to 70 % by weight of diethyl oxalate.</p>
<p>An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of brornoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of 1,3-dimethyl-2-imidazolidinone; to 20 % by weight of an aromatic hydrocarbon; and to 70 % by weight of diethyl oxalate.</p>
<p>An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 15 %byweight of anonionic surf actant which has polyalkylene oxide structure in the molecule; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of l,3-dimethyl-2-imidazolidinone; 5 to 20 % by weight of an aromatic hydrocarbon; and to 70 % by weight of diethyl oxalate.</p>
<p>An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 1 26 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of N-rnethyl-2-pyrrolidone; to 20 % by weight of an aromatic hydrocarbon; and to 70 % by weight of diethyl oxalate; and the ratio by weight of diflufenican and the sorbitan fatty acid ester is 1: 0.2 to 1: 1.5; and and the ratio by weight of N-rnethyl-2-pyrrolidone and diethyl oxalate is 1 0.1 to 1 1.</p>
<p>An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynhl=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of N,N-dimethylacetamide; 5 to 20 % by weight of an aromatic hydrocarbon; and to 70 % by weight of diethyl oxalate; and the ratio by weight of diflufenican and the sorbitan fatty acid ester is 1: 0.2 to 1 1.5; and and the ratio by weight of N.N-dimethylacetamide and diethyl oxalate is 1: 0.1 to 1 1.</p>
<p>An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 10 % by weight of an a.lkylbenzenesulfonic acid salt; 3 to 30 % by weight of 1,3-diinethyl-2-imidazolidinone; 5 to 20 % by weight of an aromatic hydrocarbon; and to 70 % by weight of diethyl oxalate; and the ratio by weight of diflufenican and the sorbitan fatty acid ester is 1 0.2 to 1: 1.5; and and the ratio by weight of 1,3-dimethyl-2-imidazolidinone and sum of an aromatic hydrocarbon and diethyl oxalate is 1 0.1 to 1 1.</p>
<p>An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; and to 90 % by weight of diethyl oxalate.</p>
<p>An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 15 % byweight of a nonionic surfactant which has polyalkylene oxide structure in the molecule; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; and 10 to 90 % by weight of diethyl oxalate.</p>
<p>An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of 1,3-dimethyl-.2-imiclazolidinone; and to 90 % by weight of diethyl oxalate.</p>
<p>An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 15 %byweightofanonionicsurfactantwhichhaspolyalkylene oxide structure in the molecule; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of 1,3-d.imethyl-2-imidazolidinone; and to 90 % by weight of diethyl oxalate.</p>
<p>An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of 1,3-dimethyl-2-imidazolidinone; to 20 % by weight of an aromatic hydrocarbon; and 5 to 70 % by weight of diethyl oxalate.</p>
<p>An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to].5 %byweightofanonionicsurfactantwhichhaspolyalkylene oxide structure in the molecule; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of 1,3-dirnethyl-2-imidazolidinone; to 20 % by weight of an aromatic hydrocarbon; and to 70 % by weight of diethyl oxalate.</p>
<p>An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; and to 90 % by weight of diethyl oxalate and the ratio by weight of diflufenican and the sorbitan fatty acid ester is 1: 0.2 to 1: 1.5.</p>
<p>An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 15 % by weight of anonionic surfactant whichhas polyalkylene oxide structure in the molecule; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; and to 90 % by weight of diethyl oxalate and the ratio by weight of diflufenican and the sorbitan fatty acid ester is 1: 0.2 to 1: 1.5.</p>
<p>An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of 1,3-dimethyl-2-imidazolidinone; and to 90 % by weight of diethyl oxalate; and the ratio by weight of diflufenican and the sorbitan fatty acid ester is 1 0.2 to 1 1.5.</p>
<p>An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0. 5 to 15 % byweight of anonionic surf actant which has polyalkylene oxide structure in the molecule; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of 1,3-dimethyl-2-imidazolidinone; and to 90 % by weight of diethyl oxalate; and the ratio by weight of diflufenican and the sorbitan fatty acid ester is 1: 0.2 to 1: 1.5.</p>
<p>An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 10 % by weight of an.alkylbenzenesulfonic acid salt; 3 to 30 % by weight of 1,3-dimethyl-2-imidazolidinone; to 20 % by weight of an aromatic hydrocarbon; and to 70 % by weight of diethyl oxalate; and the ratio by weight of diflufenican and the sorbitan fatty acid ester is 1: 0.2 to 1: 1. 5, and the ratio by weight of diflufenican and the sorbitan fatty acid ester is 1: 0.2 to 1: 1.5.</p>
<p>An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 15% by weight of anonionic surf actant which has polyalkylene oxide structure in the molecule; 0.5 to 10 % by weight of an alkylberxzenesulfonic acid salt; 3 to 30 % by weight of 1,3-dimethyl-2-imidazolidinone; to 20 % by weight of an aromatic hydrocarbon; and to 70 % by weight of diethyl oxalate; and the ratio by weight of diflufenican and the sorbitan fatty acid ester is 1 0.2 to 1: 1. 5, and the ratio by weight of diflufenican and the sorbitan fatty acid ester is 1: 0.2 to 1: 1.5.</p>
<p>An emulsifiable concentrate comprising 0.5 to 5 % by weight of diflufenican; 1. to 30 % by weight of bromoxynil=octanoa.te; 1 to 30 % by weight of ioxynhl=octanoate; 0.5 to 10 % by weight of an anionic surfactant; 0.5 to 10 % by weight of a nonionic surfactant; 1 to 40 % by weight of an aromatic hydrocarbon; 3 to 30 % by weight of N-methyl-2-pyrrolidone; 5 to 80 % by weight of 1,3-dimethyl-2-imidazolidinone; and to 80 % by weight of the compound shown by the formula (1).</p>
<p>An emulsifiable concentrate comprising 2 to 5 % by weight of diflufenican; 15 to 20 % by weight of bromoxynhl=octanoate; 12 to 18 % by weight of ioxynil=octanoate; 1 to 5 % by weight of an anionic surfactant; 1 to 5 % by weight of a nonionic surfactant; 1 to 10 % by weight of an aromatic hydrocarbon; 2 to B % by weight of N-methyl-2-pyrrolidone; to 20 % by weight of 1,3-dimethyl-2-imidazolidinone; and to 80 % by weight of the compound shown by the formula (1).</p>
<p>An emulsifiable concentrate essentially consisting of * 32 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of an anionic surfactant; 0.5 to 10 % by weight of a nonionic surfactant; 1 to 40 % by weight of an aromatic hydrocarbon; 3 to 30 % by weight of N-methyl-2-pyrrolidOfle; to 80 % by weight of 1,3-dimethyl-2-imidazolidiflofle; and to 80 % by weight of the compound shown by the formula (1).</p>
<p>An emulsifiable concentrate essentially consisting of 2 to 5 % by weight of diflufenican; to 20 % by weight of bromoxynil=octanoate; 12 to 18 % by weight of ioxynil=octanoate; 1 to 5 % by weight of an anionic surfactant; 1 to 5 % by weight of a nonionic surfactant; 1 to 10 % by weight of an aromatic hydrocarbon; 2 to 8 % by weight of N-methyl-2-pyrrolidOfle; to 20 % by weight of 1,3-dimethyl-2-imidaO1idiflOfle; and 50 to 80 % by weight of the compound shown by the formula (1).</p>
<p>An emulsifiable concentrate essentially consisting of 2 to 5 % by weight of diflufenican; to 20 % by weight of bromoxynil=octanoate; 12 to 18 % by weight of ioxynil=octanoate; 1 to 5 % by weight of an anionic surfactant; 1 to 5 % by weight of a nonionic surfactant; 1 to 10 % by weight of an aromatic hydrocarbon; 2 to 8 % by weight of N-methyl-2-pyrrolidone; to 20 % by weight of 1,3-dimethyl-2-imidazolidinone; and rest of the compound shown by the formula (1).</p>
<p>An emulsifiable concentrate comprising 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 0.5 to 10 % byweight of a nonionic surfactant which has polyalkylene oxide structure in the molecule; 1 to 40 % by weight of an aromatic hydrocarbon; 3 to 30 % by weight of N-methyl-2-pyrrolidone; to 80 % by weight of 1,3-dimethyl-2-imidazolidinone; and to 80 % by weight of the compound shown by the formula (1).</p>
<p>An emulsifiable concentrate comprising 2 to 5 % by weight of diflufenican; to 20 % by weight of bromoxynil=octanoate; 12 to 18 % by weight of ioxynil=octanoate; 1 to 5 % by weight of an alkylbenzenesulfonic acid salt; 1 to 5 % by weight of a nonionic surfactant which has polyalkylene oxide structure in the molecule; 1 to 10 % by weight of an aromatic hydrocarbon; 2 to 8 % by weight of N-methyl-2-pyrrolidone; 10 to 20 % by weight of 1,3-dimethyl-2-imidazolidinone; and to 80 % by weight of the compound shown by the formula (1).</p>
<p>An emulsifiable concentrate essentially consisting of 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynhl=octanoate; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 0.5 to 10 % by weight of a nonionic surf actant which has polyalkylene oxide structure in the molecule; 1 to 40 % by weight of an aromatic hydrocarbon; 3 to 30 % by weight of N-methyl-2-pyrrolidone; to 80 % by weight of 1,3-dimethyl-2-imidazolidinone; and to 80 % by weight of the compound shown by the formula (1).</p>
<p>An emulsifiable concentrate essentially consisting of 2 to 5 % by weight of diflufenican; to 20 % by weight of bromoxynil=octanoate; 12 to 18 % by weight of ioxynil=octanoate; 1 to 5 % by weight of an alkylbenzenesulfonic acid salt; 1 to 5 % by weight of a nonionic surfactant which has polyalkylene oxide structure in the molecule; 1 to 10 % by weight of an aromatic hydrocarbon; 2 to 8 % by weight of N-methyl-2-pyrrolidone; 10 to 20 % by weight of 1,3-dimethyl-2-imidazolidinone; and to 80 % by weight of the compound shown by the formula (1).</p>
<p>An emulsifiable concentrate essentially consisting of 2 to 5 % by weight of diflufenican; 15 to 20 % by weight of bromoxynil=octanoate; 12 to 18 % by weight of ioxynil=octanoate; 1 to 5 % by weight of an alkylbenzenesulfonic acid salt; 1 to 5 % by weight of a nonionic surf actant which has polyalkylene oxide structure in the molecule; 1 to 10 % by weight of an aromatic hydrocarbon; 2 to 8 % by weight of N-methyl-2-pyrrolidone; to 20 % by weight of 1,3-dimethyl-2-imidazolidinone; and rest of the compound shown by the formula (1).</p>
<p>An emulsifiable concentrate comprising 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of calcium dodecyl benzene sulfonate; 0.5 to 10 % by weight of polyalkyleneoxide block copolymer; 1 to 40 % by weight of an aromatic hydrocarbon; 3 to 30 % by weight of N-methyl-2-pyrro].idone; to 80 % by weight of 1,3-dimethyl-2-imidazolidinone; arid 5 to 80 % by weight of diethyl oxalate.</p>
<p>An emulsifiable concentrate comprising 2 to 5 % by weight of diflufenican; to 20 % by weight of bromoxynil=octanoate; 12 to 18 % by weight of ioxynil=octanoate; 1 to 5 % by weight of calcium dodecyl benzene sulfonate; 1 to 5 % by weight of polyalkyleneoxide block copolymer; 1 to 10 % by weight of an aromatic hydrocarbon; 2 to 8 % by weight of N-methyl-2-pyrrolidone; 10 to 20 % by weight of 1,3-dimethyl-2-imidazolidinone; and to 80 % by weight of diethyl oxalate.</p>
<p>An emulsifiable concentrate essentially consisting of 0.5 to 5 % by weight of diflufenican; * 36 1. to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of calcium dodecyl benzene sulfonate; 0.5 to 10 % by weight of polyalkyleneoxide block copolymer; 1 to 40 % by weight of an aromatic hydrocarbon; 3 to 30 % by weight of N-methyl-2-pyrrolidone; to 80 % by weight of 1,3-dimethyl-2-imidazolidinone; and to 80 % by weight of diethyl oxalate.</p>
<p>An emulsifiable concentrate essentially consisting of 2 to 5 % by weight of diflufenican; to 20 % by weight of bromoxynil=octanoate; 12 to 18 % by weight of ioxynil=octanoate; 1 to 5 % by weight of calcium dodecyl benzene sulfonate; 1 to S % by weight of polyalkyleneoxide block copolymer; 1 to 10 % by weight of an aromatic hydrocarbon; 2 to 8 % by weight of N-methyl-2-pyrrolidone; to 20 % by weight of 1.3-dimethyl-2-.imidazolidinone; and to 80 % by weight of diethyl oxalate.</p>
<p>An emulsifiable concentrate essentially consisting of 2 to 5 % by weight of diflufenican; to 20 by weight of bromoxynil=octanoate; 12 to 18 % by weight of ioxynil=octanoate; 1 to 5 % by weight of calcium dodecyl benzene sulfonate; 1 to 5 % by weight of polyalkyleneoxide block copolymer; 1 to 10 % by weight of an aromatic hydrocarbon; 2 to 8 % by weight of N-methyl-2-pyrrolidone; to 20 % by weight of 1,3-dimethyl-2--imidazolidinone; and rest of diethyl oxalate.</p>
<p>An emulsifiable concentrate comprising 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynhl=octanoate; 0.5 to 10 % by weight of calcium doclecyl benzene sulfonate; 0.5 to 10 % by weight of butylpolyalkyleneoxide block copolynier; 1 to 40 % by weight of an aromatic hydrocarbon; 3 to 30 % by weight of N-methyl-2-pyrrolidone; to 80 % by weight of 1,3-dimethyl-2-imidazolidinone; and to 80 % by weight of diethyl oxalate.</p>
<p>An emulsifiable concentrate comprising 2 to 5 % by weight of diflufenican; to 20 % by weight of bromoxynil=octanoate; 12 to 18 % by weight of ioxynil=octanoate; 1 to 5 % by weight of calcium dodecyl benzene sulfonate; 1 to 5 % by weight of butylpolyalkyleneoxide block copolymer; 1 to 10 % by weight of an aromatic hydrocarbon; 2 to 8 % by weight of N-methyl-2-pyrrolidone; to 20 % by weight of 1,3-dimethyl-2-imidazolidinone; and to 80 % by weight of diethyl oxalate.</p>
<p>An emulsifiable concentrate essentially consisting of 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of brornoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of calcium dodecyl benzene sulfonate; 0.5 to 10 % by weight of butylpolyalkYlefleoxide block copolymer; 1 to 40 % by weight of an aromatic hydrocarbon; 3 to 30 % by weight of N-methyl-2-pyrrOlidone; to 80 % by weight of and 5 to 80 % by weight of diethyl oxalate.</p>
<p>An emulsifiable concentrate essentially consisting of 2 to 5 % by weight of diflufenicafl; to 20 % by weight of bromoxynil=octaflOate; 12 to 18 % by weight of ioxynil=octanoate; 1 to 5 % by weight of calcium dodecyl benzene sulfonate; 1 to 5 % by weight of butylpolyalkylefleOxide block copolymer; 1 to 10 % by weight of an aromatic hydrocarbon; 2 to 8 % by weight of Nmethyl-2-PYrrOlid0fle 10 to 20 % by weight of l,3_dimethyl_2irflidaZO1idifl0r and to 80 % by weight of diethyl oxalate.</p>
<p>An emulsifiable concentrate essentially consisting of 3 to 5 % by weight of diflufenican; 15 to 20 % by weight of bromoxynilOCtafloate 12 to 18 % by weight of ioxyniloctaflOate 1 to 5 % by weight of calcium dodecyl benzene sulfonate; 1 to 5 % by weight of butylpolyalkylefleOXide block copolymer; 1 to 10 % by weight of an aromatic hydrocarbon; 2 to 8 % by weight of N_methyl_2-PYrrOlidOfle to 20 % by weight of 1,3_diethyl_2_imidaZ0lidir0 and rest of diethyl oxalate.</p>
<p>An emulsifiable concentrate comprising 1 39 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of an anionic surfactant; 0.5 to 10%byweight ofanonionicsurfactantwhichhaspolyalkylene oxide structure in the molecule; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 1 to 40 % by weight of an aromatic hydrocarbon; and to 80 % by weight of the compound shown by the formula (1).</p>
<p>An emulsifiable concentrate comprising 2 to 5 % by weight of diflufenican; to 20 % by weight of bromoxynil=octanoate; to 15 % by weight of ioxynil=octanoate; 1 to 5 % by weight of an anionic surfactant; 3 to 8 % by weight of a nonionic surfactant which has polyalkylene oxide structure in the molecule; 0.5 to 3 % by weight of a sorbitan fatty acid ester; 1 to 10 % by weight of an aromatic hydrocarbon; and 50 to 80 % by weight of the compound shown by the formula (1).</p>
<p>An emulsifiable concentrate essentially consisting of 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynhl=octanoate; 1 to 30 % by weight of ioxynhl=octanoate; 0.5 to 10 % by weight of an anionic surfactant; 0.5 to 10 % by weight of anonionic surf actant which has polyalkylene oxide structure in the molecule; 0.5 to 10 % by weight of a sorbitan fatty acid ester; S 40 1 to 40 % by weight of an aromatic hydrocarbon; and to 80 % by weight of the compound shown by the formula (1).</p>
<p>An emulsifiable concentrate essentially consisting of 2 to 5 % by weight of diflufenica.n; to 20 % by weight of bromoxynhl=octanoate; to 15 % by weight of ioxynil=octanoate; 1 to 5 % by weight of an anionic surfactant; 3 to 8 % by weight of a nonionic surf actant which has polyalkylene oxide structure in the molecule; 0.5 to 3 % by weight of a sorbitan fatty acid ester; 1 to 10 % by weight of an aromatic hydrocarbon; and to 80 % by weight of the compound shown by the formula (1).</p>
<p>An emulsifiable concentrate essentially consisting of 2 to 5 % by weight of diflufenican; to 20 % by weight of bromoxynil=octanoate; to 15 % by weight of ioxynil=octanoate; 1 to 5 % by weight of an anionic surfactant; 3 to 8 % by weight of a nonionic surf actant which has polyalkylene oxide structure in the molecule; 0.5 to 3 % by weight of a sorbitan fatty acid ester; 1 to 10 % by weight of an aromatic hydrocarbon; and rest of the compound shown by the formula (1).</p>
<p>An emulsifiable concentrate comprising 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 1 41 0.5 to 10 % by weight of calcium dodecyl benzene sulfonate; 0.5 to 10 % by weight of polyoxypropylene tristyryl phenyl ether; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 1 to 40 % by weight of an aromatic hydrocarbon; and 5 to 80 % by weight of the compound shown by the formula (1).</p>
<p>An emulsifiable concentrate comprising 2 to 5 % by weight of diflufenican; to 20 by weight of bromoxynil=octanoate; 5 to 15 % by weight of ioxynil=octanoate; 1 to 5 % by weight of calcium dodecyl benzene sulfonate; 3 to 8 % by weight of polyoxypropylene tristyryl phenyl ether; 0.5 to 3 % by weight of a sorbitan fatty acid ester; 1 to 10 % by weight of an aromatic hydrocarbon; and 50 to 80 % by weight of the compound shown by the formula (1).</p>
<p>An emulsifiable concentrate essentially consisting of 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxyniloctanoate; 0.5 to 10 % by weight of calcium dodecyl benzene sulfonate; 0.5 to 10 % by weight of polyoxypropylene tristyryl phenyl ether; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 1 to 40 % by weight of an aromatic hydrocarbon; and 5 to 80 % by weight of the compound shown by the formula (1).</p>
<p>An emulsifiable concentrate essentially consisting of 2 to 5 % by weight of diflufenican; to 20 % by weight of bromoxynil=octanoate; * 42 to 15 % by weight of ioxynil=octanoate; 1 to 5 % by weight of calcium dodecyl benzene sulfonate; 3 to 8 % by weight of polyoxypropylene tristyryl phenylether; 0.5 to 3 % by weight of a sorbitan fatty acid ester; 1 to 10 % by weight of an aromatic hydrocarbon; and to 80 % by weight of the compound shown by the formula (1).</p>
<p>An emulsifiable concentrate essentially consisting of 2 to 5 % by weight of diflufenican; 10 to 20 % by weight of bromoxynil=octanoate; to 15 % by weight of ioxynil=octanoate; 1 to 5 % by weight of calcium dodecyl benzene sulfonate; 3 to 8 % by weight of polyoxypropylene tristyry]. phenyl ether; 0.5 to 3 % by weight of a sorbitan fatty acid ester; 1 to 10 % by weight of an aromatic hydrocarbon; and rest of the compound shown by the formula (1).</p>
<p>An emulsifiable concentrate comprising 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of calcium dodecyl benzene sulfonate; 0.5 to 10 % by weight of polyoxypropylene tristyryl phenyl ether; 0.5 to 10 % by weight of sorbitan mono laurate; 1 to 40 % by weight of an aromatic hydrocarbon; and to 80 % by weight of diethyl oxalate.</p>
<p>An emulsifiable concentrate comprising 2 to 5 % by weight of diflufenican; to 20 % by weight of bromoxynil=octanoate; to 15 % by weight of ioxynhl=octanoate; 1 to 5 % by weight of calcium dodecyl benzene sulfonate; 3 to 8 % by weight of polyoxypropylene tristyryl phenyl ether; 0.5 to 3 % by weight of sorbitan mono laurate; 1 to 10 % by weight of an aromatic hydrocarbon; and to 80 % by weight of diethyl oxalate.</p>
<p>An emulsifiable concentrate essentially consisting of 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynhl=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of calcium dodecyl benzene sulfonate; 0.5 to 10 % by weight of polyoxypropylene tristyryl phenyl ether; 0.5 to 10 % by weight of sorbitan mono laurate; 1 to 40 % by weight of an aromatic hydrocarbon; and to 80 % by weight of diethyl oxalate.</p>
<p>An emulsifiable concentrate essentially consisting of 2 to 5 % by weight of diflufenican; to 20 % by weight of bromoxynil=octanoate; to 15 % by weight of ioxynil=octanoate; 1 to 5 % by weight of calcium dodecyl benzene sulfonate; 3 to 8 % by weight of polyoxypropylene tristyryl phenyl ether; 0.5 to 3 % by weight of sorbitan mono laurate; 1 to 10 % by weight of an aromatic hydrocarbon; and to 80 % by weight of diethyl oxalate.</p>
<p>An emulsifiable concentrate essentially consisting of 2 to 5 % by weight of diflufenican; to 20 % by weight of bromoxynil=octanoate; to 15 % by weight of ioxynil=octanoate; 1 to 5 % by weight of calcium dodecyl benzene sulfonate; 3 to 8 % by weight of polyoxypropylene tristyryl phenyl ether; 0.5 to 3 % by weight of sorbitan mono laurate; 1 to 10 % by weight of an aromatic hydrocarbon; and rest of diethyl oxalate.</p>
<p>An emulsifiable concentrate comprising 0.5 to 5 % by weight of diflufenican; 1 to 30 by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of an anionic surfactant; 0.5 tolO % byweightofanonionicsurfactantwhichhaspolyalkylene oxide structure in the molecule; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 1 to 40 % by weight of an aromatic hydrocarbon; to 80 % by weight of 1,3-dimethyl-2-imidazoridione; and 5 to 80 % by weight of the compound shown by the formula (1).</p>
<p>An emulsifiable concentrate comprising 2 to 5 % by weight of diflufenican; to 20 % by weight of bromoxynil=octanoate; 5 to 15 % by weight of ioxynil=octanoate; 1 to 5 % by weight of an anionic surfactant; 3 to 8 % by weight of a nonionic surfactant which has polyalkylene oxide structure in the molecule; 0.5 to 3 % by weight of a sorbitan fatty acid ester; 1, 45 1 to 15 % by weight of an aromatic hydrocarbon; to 50 % by weight of 1,3-dimethyl-2-imidazoridione; and to 50 % by weight of the compound shown by the formula (1).</p>
<p>An emulsifiable concentrate essentially consisting of 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of an anionic surf actant; 0.5 to 10 %byweight ofanonionicsurfactantwhichhaspolyalkylene oxide structure in the molecule; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 1 to 40 % by weight of an aromatic hydrocarbon; to 80 % by weight of 1,3-dimethyl-2-iinidazoridiOne; and 5 to 80 % by weight of the compound shown by the formula (1).</p>
<p>An emulsifiable concentrate essentially consisting of 2 to 5 % by weight of diflufenican; to 20 % by weight of bromoxynil=octanoate; 5 to 15 % by weight of ioxynil=octanoate; 1 to 5 % by weight of an anionic surfactant; 3 to 8 % by weight of a norxionic surfactant which has polyalkylene oxide structure in the molecule; 0.5 to 3 % by weight of a sorbitan fatty acid ester; 1 to 15 % by weight of an aromatic hydrocarbon; to 50 % by weight of 1,3-dimethyl-2-imidazoridione; and to 50 % by weight of the compound shown by the formula (1).</p>
<p>An emulsifiable concentrate essentially consisting of 46 2 to 5 % by weight of diflufenican; to 20 % by weight of bromoxynil=octanoate; to 15 % by weight of ioxynil=octanoate; 1 to 5 % by weight of an anionic surfactant; 3 to 8 % by weight of a nonionic surfactant which has polyalkylene oxide structure in the molecule; 0.5 to 3 % by weight of a sorbitan fatty acid ester; 1 to 15 by weight of an aromatic hydrocarbon; to 50 % by weight of 1,3-dimethyl-2-imidazoridiofle; and rest of the compound shown by the formula (1).</p>
<p>An emulsifiable concentrate comprising 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of calcium dodecyl benzene sulfonate; 0.5 to 10 % by weight of polyoxypropylene tristyryl phenyl ether; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 1 to 40 % by weight of an aromatic hydrocarbon; 5 to 80 % by weight of 1,3-dimethyl-2-imidazoridione; and to 80 % by weight of the compound shown by the formula (1).</p>
<p>An emulsifiable concentrate comprising 2 to 5 % by weight of diflufenican; 10 to 20 % by weight of bromoxynil=octanoate; to 15 % by weight of ioxynil=octanoate; 1 to 5 % by weight of calcium dodecyl benzene sulfonate; 3 to 8 % by weight of polyoxypropylene tristyryl phenyl ether; 0.5 to 3 % by weight of a sorbitan fatty acid ester; 1 to 15 % by weight of an aromatic hydrocarbon; to 50 % by weight of 1,3-dimethyl-2--imidazoridione; and to 50 % by weight of the compound shown by the formula (1).</p>
<p>An emulsifiable concentrate essentially consisting of 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of brornoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of calcium dodecyl benzene sulfonate; 0.5 to 10 by weight of polyoxypropylene tristyryl phenyl ether; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 1 to 40 % by weight of an aromatic hydrocarbon; to 80 % by weight of l,3-dimethyl--2-imidazoridione; and to 80 % by weight of the compound shown by the formula (1).</p>
<p>An emulsifiable concentrate essentially consisting of 2 to 5 % by weight of diflufenican; to 20 % by weight of brornoxynil=octanoate; to 15 % by weight of ioxynil=octanoate; 1 to 5 % by weight of calcium dodecyl benzene sulfonate; 3 to 8 % by weight of polyoxypropylene tristyryl phenyl ether; 0.5 to 3 % by weight of a sorbitan fatty acid ester; 1 to 15 % by weight of an aromatic hydrocarbon; to 50 % by weight of 1,3-dimethyl-2-imidazoridione; and 10 to 50 % by weight of the compound shown by the formula (1).</p>
<p>An emulsifiable concentrate essentially consisting of 2 to 5 % by weight of diflufenican; to 20 % by weight of bromoxynil=octanoate; to 15 % by weight of ioxynhl=octanoate; 1 to 5 % by weight of calcium dodecyl benzene sulfonate; 3 to 8 % by weight of polyoxypropylene tristyryl phenyl ether; 0.5 to 3 % by weight of a sorbitan fatty acid ester; 1 to 15 % by weight of an aromatic hydrocarbon; to 50 % by weight of 1,3-dimethyl-2-imidazoridione; and rest of the compound shown by the formula (1) An emulsifiable concentrate comprising 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of calcium dodecyl benzene sulfonate; 0.5 to 10 % by weight of polyoxypropylene tristyryl phenyl ether; 0.5 to 10 % by weight of sorbitan mono laurate; 1 to 40 % by weight of an aromatic hydrocarbon; to 80 % by weight of 1,3-dimethyl-2-imidazoridione; and to 80 % by weight of diethyl oxalate.</p>
<p>An emulsifiable concentrate comprising 2 to 5 % by weight of diflufenican; to 20 % by weight of bromoxynil=octanoate; to 15 % by weight of ioxynil=octanoate; 1 to 5 % by weight of calcium dodecyl benzene sulfonate; 3 to 8 % by weight of polyoxypropylene tristyryl phenyl ether; 0.5 to 3 % by weight of sorbitan mono laurate; 1 to 15 % by weight of an aromatic hydrocarbon; to 50 % by weight of 1,3-dimethyl-2-imidazoridione; and to 50 % by weight of diethyl oxalate.</p>
<p>An emulsifiable concentrate essentially consisting of 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of calcium dodecy]. benzene sulfonate; 0.5 to 10 % by weight of polyoxypropylene tristyryl phenyl ether; 0.5 to 10 % by weight of sorbitan mono laurate; 1 to 40 % by weight of an aromatic hydrocarbon; 5 to 80 % by weight of 1,3-dimethyl-2-imidazoridione; and to 80 % by weight of diethyl oxalate.</p>
<p>An emulsifiable concentrate essentially consisting of 2 to 5 % by weight of diflufenican; 10 to 20 % by weight of bromoxynil=octanoate; to 15 % by weight of ioxynhl=octarioate; 1 to 5 % by weight of calcium dodecyl benzene sulfonate; 3 to B % by weight of polyoxypropylene tristyryl phenyl ether; 0.5 to 3 % by weight of sorbitan mono laurate; 1 to 15 % by weight of an aromatic hydrocarbon; to 50 % by weight of 1,3-dimethyl-2-imidazoridione; and to 50 % by weight of diethy]. oxalate.</p>
<p>An emulsifiable concentrate essentially consisting of 2 to 5 % by weight of diflufenican; to 20 % by weight of bromoxynil=octanoate; to 15 % by weight of ioxynil=octanoate; 1 to 5 % by weight of calcium dodecyl benzene sulfonate; 3 to B % by weight of polyoxypropylene tristyryl phenyl ether; 0.5 to 3 % by weight of sorbitan mono laurate; 1 to 15 % by weight of an aromatic hydrocarbon; to 50 % by weight of 1,3-dimethyl-2-imidazoridione; and rest of diethyl oxalate.</p>
<p>The emulsifiable concentrate of the present invention can be produced by mixing the component of the emulsifiable concentrate of the present invention, then stirring until the mixture becomes uniform. The temperature while stirring is usually in the range between room temperature and 85 C. The mixing order of the component of the emulsifiable concentrate of the present invention may be properly decided.</p>
<p>The emulsifiable concentrate of the present invention is usually applied after diluted with water to a weed or soil surface where weed is predicted to grow. An aqueous composition which is obtained by diluted the emulsifiable concentrate of the present invention with water is a diluted composition of the emulsifiable concentrate of the present invention with water of the amount of usually 10 to 5000 times, preferably 20 to 2500 times based on the amount of the emulsifiable concentrate of the present invention. Generally, the water used to dilution may be soft water or hard water. Auxiliaries such as spreader may be added to the water used to dilution, if necessary.</p>
<p>Though the application amount of the aqueous composition which is obtained by diluted the emulsifiable concentrate of the present invention with water may vary depending on the ratio of diflufenican, bromoxynil=octanoate and ioxynil=octanoate; weather conditions; the treatment timing; the treatment place; the kind of a weed which is controlled, it is usually 40 to 2000g. preferably 80 to l000g per hectare as total weight of diflufenican, bromoxynil=octanoate and ioxynil=octanoate.</p>
<p>EXAMPLES</p>
<p>Hereinafter, the present invention will be further explained in detail by way of Preparation Examples and Test Examples, but the present invention is not limited to these</p>
<p>examples.</p>
<p>Preparation Example 1-1 Diflufenican(purity 91 %, 3.6 g as active ingredient), bromoxynil=octanoate(purity95. 4%, 17.33 gas activeingredient) and ioxynil=octanoate(purity 96 %, 9.65 g as active ingredient) were added to diethyl oxalate(40.54 g) under heating and were dissolved. Then calcium dodecyl benzene sulfonate (Rhodacal60/BE, surfactant produced by Rhodia Nicca; 3.83 g) and polyoxypropylene castor oil(Alkaniuls 0R40, surfactant produced by Rhodia Nicca; 3.83 g) were added to it. Furthermore, aromatic hydrocarbon(mainly dO to Cli alkylbenzene, Solvesso 150 ND, CAS No. 64742-94-5, Exxon Mobil Chemical Company) was added until total amount being 100 ml, and stirred until uniform solution to give the emulsifiable concentrate of the present invention(referredas the emulsifiable concentrate of the present invention 1-1, hereinafter).</p>
<p>Test Example 1-1</p>
<p>The emulsifiable concentrate of the present invention 1-1 was diluted by CIPAC standard water D (342ppm) for 100 times in a 100 ml -graduated cylinder with stopper. It was left at 30 C for 2 hours, andwas observed the stability of the emulsion. After that, the aqueous composition which was obtained by diluted the emulsifiable concentrate of the present invention 1-1 with water kept stable emulsion.</p>
<p>Preparation Example 1-2 Diflufenican(4.0 gas active ingredient), calcium dodecyl benzene sulfonate (Rhodacal 70, surfactant produced by Rhodia Nicca; 4.75 g) and polyoxyethylene-polyoxypropylene tristyryl phenyl ether(Soprophor 796/P. surfactant produced by Rhodia Nicca; 2.25 g) were measured in a 100 ml graduated flask at 20 C. Then diethyl oxalate was added until the total amount being 100 ml. It was stirreduntil uniform solution to give the emulsifiable concentrate of the present invention( referred as the emulsifiable concentrate of the present invention 1-2, hereinafter).</p>
<p>Preparation Example 1-3 Diflufenican(4.0 gas active ingredient), calciuindodecyl benzene sulfonate (Rhodacal 70, surfactant produced by Rhodia Nicca; 5.50 g) and polyoxyethylene-polyoxypropylene tristyryl phenyl ether(Soprophor 796/P. surfactant produced by Rhodia Nicca; 1.50 g) were measured in a 100 ml graduated flask at 20 0 Then diethyl oxalate was added until the total amount being 100 ml. It was stirreduntiluniformsolutionto give the emulsifiable concentrate of the present invention(referredas the emulsifiable concentrate of the present invention 1-3 hereinafter).</p>
<p>Test Example 1-2</p>
<p>Each of the emulsifiable concentrate of the present invention 1 and 2 was diluted by CIPAC standard water D (342pprn) for 100 times in a 100 ml -graduated cylinder with stopper. They were left at 30 C for 2 hours, and were observed the stability of the emulsion. After that, the aqueous composition which were obtained by diluting the emulsifiable concentrate of the present invention 1-2 and 1-3 with water kept stable emulsion.</p>
<p>Preparation Example 1-4 Diflufenican(3.71 g as active ingredient), brornoxynil=octanoate(18.22 g as active ingredient), ioxynil=octanoate( 9.63g as active ingredient), calcium dodecyl benzene sulfonate (Rhodacal 70, surfactant produced by Rhodia Nicca; 3.17 g) and polyoxyethylene-polyoxypropylene tristyryl phenyl ether(Soprophor 796/P. surfactant produced by Rhodia Nicca; 4.52 g) were measured in a 100 ml graduated flask at 20 C.</p>
<p>Then diethyl oxalate was added until the total amount being 100 ml. Itwas stirreduntiluniformsolutionto givetheemulsifiable concentrate of the present invent ion( referred as the emulsifiable concentrate of the present invention 1-4 hereinafter).</p>
<p>Preparation Example 1-5 Diflufenican(3.71 g as active ingredient), bromoxynil=octanoate(18.22 g as active ingredient), ioxynil=octanoate(9. 63g as active ingredient), calcium dodecy].</p>
<p>benzene sulfonate (Rhodacal 70, surfactant produced by Rhodia Nicca; 3.17 g) and polyoxyethylene-polyoxypropylene tristyryl phenyl ether(Soprophor 796/P, surfactarit produced by Rhodia Nicca; 4.52 g) were measured in a 100 ml graduated flask at 20 C. Then diethyl oxalate(40. 39 g) and Solvesso 200 ND(mainly Cli to Cl4alkylnaphthalene, aromatichydrocarbon, ExxonMobilChemical Company; 20.16 g) were added. It was stirred until uniform solution to give the emulsifiable concentrate of the present invention(ref erred as the emulsifiable concentrate of the present invention 1-5 hereinafter).</p>
<p>Test Example 1-3</p>
<p>Each of the emulsifiable concentrate of the present jnventionl-4andl-5wasdilutedbyClPACstandardwaterD(342ppm) for 100 times in a 100 ml -graduated cylinder with stopper. They were left at 30 C for 2 hours, and were observed the stability of the emulsion. After that, the aqueous composition which were obtained by diluting the emulsifiable concentrate of the present invention 1-4 and 1-5 with water kept stable emulsion.</p>
<p>Preparation Example 2-1 Diflufenican(purity 93.2 %, 4.0 g as active ingredient), calcium dodecyl benzene sulfonate (Rhodacal 70, surf actant produced by Rhodia Nicca; 4.00 g), polyoxyethylene -polyoxypropylene tristyryl phenyl ether(Soprophor 796/P, produced by Rhodia Nicca; 3.00 g) and 1,3-dimethyl-2-imidazolidinone(45.00 g) were measured to a 100 ml -graduated flask, and filled to 100 ml with diethyl oxalate.</p>
<p>Then it was stirred until uniform solution to give the emulsifiable concentrate of the present invention(referred as the emulsifiable concentrate of the present invention 2-1, hereinafter).</p>
<p>Preparation Example 2-2 Diflufenican(4.0 gas active ingredient), calcium dodecyl benzene sulfonate (Rhodacal 70, surfactant produced by Rhodia Nicca; 4.75 g), polyoxyethylene-polyoxypropylefle tristyryl phenyl ether(Soprophor 796/P. produced by Rhodia Nicca; 2.25 g) and 1,3-dirnethyl-2-imidazolidinone(45.00 g) were measured to a ml -graduated flask, andfilledto loomlwithdiethyloxalate.</p>
<p>Then it was stirreduntil uniform solution to give the emulsifiable concentrate of the present invention (referred as the emulsifiable concentrate of the present invention 2-2, hereinafter).</p>
<p>Preparation Example 2-3 Diflufenican(4.0 gas active ingredient), calcium dodecyl benzene sulfonate (Rhodacal 70, surfactant produced by Rhodia Nicca; 5.50 g), polyoxyethylene-polyoxypropylene tristyryl phenyl ether(Soprophor 796/P, produced by Rhodia Nicca; 1.50 g) and 1,3-dimethyl-2-imidazolidinone(45.00 g) were measured to a lOOmi -graduatedflask, andfilledto 100 mlwithdiethyl oxalate.</p>
<p>Then it was stirred until uniform solution to give the emulsifiable concentrateof thepresent invention(referredas theemulsifiable concentrate of the present invention 2-3, hereinafter).</p>
<p>Test Example 2-1</p>
<p>Each of the emulsifiable concentrate of the present invention 2-1 to 2-3 was dilutedbyClPACstandardwaterD (342ppm) for 100 times in a 100 ml -graduated cylinder with stopper. It was left at 30 C for 2 hours, and was observed the stability of the emulsion. After that, the aqueous composition which was obtained by diluting the emulsifiable concentrate of the present invention 2-1 to 2-3 with water kept stable emulsion.</p>
<p>Preparation Example 2-4 Diflufenican(4.,0 g as active ingredient), brornoxynil=octanoate(purity94.8%, 18.00 gas active ingredient), ioxynil=octanoate(purity 96 %, 10.5 g as active ingredient), calcium dodecyl benzene sulfonate (NANSA EVM62/H, surfactant produced by Huntsman; 3.00 g) and polyoxypropylene castor oil(Alkarnuls 0R40, surfactant produced by Rhodia Nicca; 6.00 g) and 1,3-dimethyl-2-imidazolidinone(45.00 g) were measured to a ml -graduated flask, and filled to 100 ml with aromatic hydrocarbon(include Cli to C14 alkylnaphthalene, Solvesso 200</p>
<p>I</p>
<p>ND, producedbyExxonMobil Chemical Company). Then it was stirred until uniform solution to give the emulsifiable concentrate of the present invention(referred as the emulsifiable concentrate of the present invention 2-4, hereinafter).</p>
<p>Preparation Example 2-5 Diflufenican(4.0 g as active ingredient), brornoxynil=octanoate(18.00 g as active ingredient), ioxynil=octanoate(10. 05 gas active ingredient), calcium dodecyl benzene sulfonate (NANSA EVM62/H, surfactant produced by Huntsman; 4.50 g) and polyoxyethylene tristyryl phenyl ether(Soprophor BSU, produced by Rhodia Nicca; 4.5 g) and 1,3-dirnethyl--2-imidazolidinone(45.00 g) were measured to a 100 ml -graduated flask, and filled to 100 ml with aromatic hydrocarbon(include Cli to C14 alkylnaphthalene, Solvesso 200 ND, producedbyExxonMobil ChemicalCompany). Then itwas stirred until uniform solution to give the emulsifiable concentrate of the present invention(referred as the emulsifiable concentrate of the present invention 2-5, hereinafter).</p>
<p>Preparation Example 2-6 Diflufenican(4.0 g as active ingredient), bromoxynil=octanoate(18.00 g as active ingredient), ioxynil=octanoate(iO.05 gas active ingredient) calcium dodecyl benzene sulfonate (NANSA EVM62/I-I, surfactant produced by Huntsman; 4.00 g) and polyoxyethylene tristyryl phenyl ether(Soprophor BSU, produced by Rhodia Nicca; 5.0 g) and i,3-dimethyl-2-imidazolidinone(45.O0 g) were measured to a 100 ml -graduated flask, and filled to 100 ml with aromatic hydrocarbon(include Cli to C14 alkylnaphthalene. Solvesso 200 ND, produced by ExxonMobil Chemical Company). Then it was stirred 4, 57 until uniform solution to give the emulsifiable concentrate of the present invention(referred as the emulsifiable concentrate of the present invention 2-6, hereinafter).</p>
<p>Test Example 2-2</p>
<p>Each of the emulsifiable concentrate of the present invention 2-4 to 2-6 was diluted byCIPAC standardwaterD (342ppm) for 100 times in a 100 ml -graduated cylinder with stopper. It was left at 30 0 C for 0.5 hours, and was observed the stability of the emulsion. After that, the aqueous composition which was obtained by diluting the emulsifiable concentrate of the present invention 2-4 to 2-6 with water kept stable emulsion.</p>
<p>Preparation Example 2-7 Diflufenican(2.0 gas active ingredient), calcium dodecyl benzene sulfonate (NANSA EVM62/H, surfactant produced by Huntsman; 3.00 g), polyoxyethylene-polyoxypropylene tristyryl phenyl ether(Soprophor 796/P, produced by Rhodia Nicca; 3.00 g) and 1,3-dimethyl-2-imidazolidinone(10.00 g) are measured to a ml -graduated flask, and fill to 100 ml with aromatic hydrocarbon(include dO to Cl]. alkylbenzene, Solvesso 150 ND, produced by Exxon Mobil Chemical Company). Then it is stirred until uniform solution to give the emulsifiable concentrate of the present invention.</p>
<p>Preparation Example 2-8 Diflufenican(4.0 g as active ingredient), bromoxynhl=octanoate(18.00 g as active ingredient), ioxynil=octanoate(1O.05 gas active ingredient), calcium dodecyl benzene sulfonate (Rodacal 70, surfactant produced by Rhodia Nicca; 3.00 g) and polyoxyethylene alkyl ether(Tensiofix 96DB10, produced by Omni Chemical; 6.0 g) and 1,3-dimethyl-2-imidazolidinone(30.00 g) are measured to a 100 ml -graduated flask, and fill to 100 ml with aromatic hydrocarbon(include Cli to C14 alkylnaphthalene, Solvesso 200 ND, produced by Exxon Mobil Chemical Company). Then it is stirred until uniform solution to give the emulsifiable concentrate of the present invention.</p>
<p>Preparation Example 2-9 Diflufenican(4.0 g as active ingredient), bromoxynil=octanoate(18.00 g as active ingredient), ioxynil=octanoate(i0.05 gas active ingredient), calcium dodecyl benzene sulfonate (NANSA EVM62/H. surfactant produced by Huntsman; 5.00 g), polyoxyethylene tristyryl phenyl ether(Soprophor BSU. produced by Rhodia Nicca; 4.00 g), 1, 3-dimethyl-2-imidazolidiflOfle (15.00 g) and aromatic hydroca.rbon(include Cli to C14 alkylnaphthalene, Solvesso 200 ND, producedbyExxonMobil Chemical Company; 10.00 g) are measured to a 100 ml -graduated flask, and fill to 100 ml with diethyl oxalate. Then it is stirred until uniform solution to give the emulsifiable concentrate of the present invention.</p>
<p>Preparation Example 2-10 Diflufenican(4.0 g as active ingredient), bromoxynil=octanoate(18.00 g as active ingredient), ioxynil=octanoate( 10.05 gas active ingredient), calcium dodecyl benzene sulfonate (NANSA EVM62/H, surfactant produced by Huntsman; 5.00 g), polyoxyethylene tristyryl phenyl ether(Soprophor BSU, produced by Rhodia Nicca; 4.00 g), 1, 3-dimethyl-2-imidaZolidiflOfle (20.00 g) and aromatic hydrocarbon(include Cli to C14 alkylnaphthalene, Solvesso 200 ND, producedbyExxonMobilChemiCalCompany; 10.00 g) aremeasured 4, 59 to a 100 ml -graduated flask, and fill to 100 ml with diethyl oxalate. Then it is stirred until uniform solution to give the emulsifiable concentrate of the present invention.</p>
<p>Preparation Example 2-11 Diflufenican(4.0 g as active ingredient), bromoxynil=octanoate(18.00 g as active ingredient), ioxynil=octanoate(10. 05 gas active ingredient), calcium dodecyl benzene sulfonate (NANSA EVM62/H, surfactant produced by Huntsman; 4.50 g), polyoxyethylene-polyoxypropylene tristyryl phenyl ether(Soprophor 796/P. surfactant produced by Rhodia Hicca; 4.50 g) and 1,3-dimethyl-2-imidazolidinone (30.00 g) are measured to a 100 ml -graduated flask, and fill to 100 ml with aromatic hydrocarbon(include dO to Cli alkylbenzene, Solvesso ND, produced by Exxon Mobil Chemical Company). Then it is stirred until uniform solution to give the emulsifiable concentrate of the present invention.</p>
<p>Preparation Example 2-12 Diflufenicari(3.72 g as active ingredient), bromoxynil=octanoate(16.74 g as active ingredient), ioxynil=octanoate(9. 35 gas active ingredient), calcium dodecyl benzene sulfonate (NANSA EVM62/H, surfactant produced by Huntsman; 4.50 g), polyoxyethylene-polyoxypropylene tristyryl phenyl ether(Soprophor 796/P. surfactant produced by Rhodia Nicca; 4.50 g) and 1,3-dimethyl-2-imidazolidinone (20.00 g) are measured to a 100 ml -graduated flask, and fill to 100 ml with aromatic hydrocarbon(include dO to Cli alkylbenzene, Solvesso ND, produced by Exxon Mobil Chemical Company). Then it is stirred until uniform solution to give the emulsifiable concentrate of the present invention.</p>
<p>Preparation Example 2-13 Diflufenican(2.68 g as active ingredient), bromoxynil=octanOate(12.06 g as active ingredient), ioxynil=octanoate(6.73 gas active ingredient), calcium dodecyl benzene sulfonate (NANSA EVM62/H, surfactant produced by Huntsman; 4.50 g), polyoxyethylene-polyoxypropylene tristyryl phenyl ether(Soprophor 796/P. surfactant produced by Rhodia Nicca; 4.50 g) and 1,3-dimethyl-2-imidazolidinone (15.00 g) are measured to a 100 ml -graduated flask, and fill to 100 ml with aromatic hydrocarbon(include dO to Cli alkylbenzene, Solvesso ND, produced by Exxon Mobil Chemical Company). Then it is stirred until uniform solution to give the emulsifiable concentrate of the present invention.</p>
<p>Preparation Example 3-1 Diflufenican(purity 93.2 %, 3.72 gas active ingredient), bromoxynil=octanOate(pUritY94. 8%, 16.74 gas active ingredient), ioxynil=octanoate(purity 96 %, 9.35 g as active ingredient), calcium dodecyl benzene sulfonate (3.67 g), polyoxyethylene tristyryl phenyl ether(HLB 12.6; 6.33 g), sorbitan mono laurate(HLB 8.6; 3.00 g), aromatic hydrocarbon(include Cii to C14 alkylnaphthalene, Solvesso 200 ND, produced by Exxon Mobil ChemicalCornpaflY; 5.00 g) andN-methyl-2-pyrrolidOfle( 5.70 g) were measured in a 100 ml graduated flask. Then diethyl oxalate was added until the total amount being 100 ml. It was stirred until uniform solution to give the emulsifiable concentrate of the present invention(referred as the emulsifiable concentrate of the present invention 3-1, hereinafter).</p>
<p>Preparation Example 3-2 At 20 *C, diflufenican(purity 93.2 %, 3.72 g as active ingredient), bromoxynil=octanoate(purity 94.8 %, 16.74 g as active ingredient), ioxynil=octanoate(purity 96 %, 9.35 g as active ingredient), calcium dodecyl benzene sulfonate (3.95 g), polyoxyethylene tristyrylphenyl ether(HLB 12.6; 7.55 g), sorbitan mono laurate(HLB 8.6; 1.50 g), aromatic hydrocarbon(include Cli to C14 alkylnaphthalene, Solvesso 200 ND, produced by Exxon Mobil Chemical Company; 10.00 g) and 1,3-dimethyl-2-imidazolidinone( 15.00 g) were measured in a 100 ml graduated flask. Then diethyl oxalate was added until the total amount being 100 ml. It was stirred until uniform solution to give the emulsifiable concentrate of the present invention ( referred as the emulsifiable concentrate of the present invention 3-2, hereinafter).</p>
<p>Preparation Example 3-3 At 20 C, diflufenican(purity 93.2 %, 2.68 g as active ingredient), brornoxynil=octanoate(purity 94.8 %, 12.06 g as active ingredient). ioxynil=octanoate(purity 96 %, 6.37 g as active ingredient), calcium dodecyl benzene sulfonate (2.70 g), polyoxyethylene tristyryl phenyl ether(HLB 12.6; 6.30 g), sorbitan mono laurate(HLB 8.6; 1.00 g) and aromatic hydrocarbon(include Cli to C14 alkylnaphthalene, Solvesso 200 ND, produced by Exxon Mobil Chemical Company; 5.00 g) were measured in a 100 ml graduated flask. Then diethyl oxalate was added until the total amount being 100 ml. It was stirred until uniform solution to give the emulsifiable concentrate of the present invention (referred as the emulsifiable concentrate of the present invention 3-3, hereinafter).</p>
<p>Test Example 3-].</p>
<p>Each of the emulsifiable concentrate of the present invention 3-1 to 3-3 was filled in the bottle. They were kept in refrigerator for 7 days at 0 C. Then each bottle was taken out from the refrigerator, and kept for about 30 minutes at room temperature. After that, it was observed whether solid substance existed or not in the bottom of the bottle. There were no solid substance in each of them, and each of them was clear and uniform solution.</p>
<p>Test Example 3-2</p>
<p>IntoalOOmi-graduated cylinderwith stopper, 99m1ofCIPAC standard water D (342ppm) were charged. The graduated cylinder was put in a thermostat andwas kept at 30 C for awhile. Further, 1 ml each of the emulsifiable concentrate of the present invention 3-1 to 3-3 were added into the graduated cylinder, and the cylinder was turned upside down 10 times at a rate of once per two seconds.</p>
<p>Then, it was put in a thermostat again and left at 30 C for 2 hours. After that, each of the state of the emulsion in the graduated cylinder was observed. Each was provided uniform emulsion state.</p>
<p>Preparation Example 3-4 At 20 C, diflufenican(purity 93.2 %, 2.68 g as active ingredient), bromoxynil=octanoate(purity 94.8 %, 12.06 g as active ingredient), ioxynil=octanoate(purity 96 %, 6.37 g as active ingredient), calcium dodecy]. benzene sulfonate (2.90 g), polyoxyethylene tristyryl phenyl ether(HLB 12.6; 12.20 g), sorbitan mono oleate(HLB 4.3; 1.00 g) and aromatic hydrocarbon(include Cli to C14 alkylnaphthalene, Solvesso 200 ND, produced by Exxon Mobil Chemical Company; 10.00 g) were measured in a 100 ml graduated flask. Then diethyl oxalate was added until the total amount being 100 ml. It was stirred until uniform solution to give the emulsifiable concentrate of the present invention(ref erred as the emulsifiable concentrate of the present invention 3-4, hereinafter).</p>
<p>Preparation Example 3-5 At 20 C, diflufenican(purity 93.2 %, 2.68 g as active ingredient), bromoxynil=octanoate(purity 94.8 %, 12.06 g as active ingredient). ioxynil=octanoate(purity 96 %, 6.37 g as active ingredient), calcium dodecyl benzene sulfonate (2.90 g), polyoxyethylene tristyryl phenyl ether(HLB 12.6; 12.20 g), sorbitan mono laurate(HLB 8.6; 1.00 g) and aromatic hydrocarbon(include Cli to C].4 alkylnaphthalene, Solvesso 200 ND, produced by Exxon Mobil Chemical Company; 10.00 g) were measured in a 100 ml graduated flask. Then diethyl oxalate was added until the total amount being 100 ml. It was stirred until uniform solution to give the emulsifiable concentrate of the present invention(ref erred as the emulsifiable concentrate of the present invention 3-5, hereinafter).</p>
<p>Test Example 3-3</p>
<p>Each of the emulsifiable concentrate of the present invention 3-4 to 3-5 was filled in the bottle. They were kept in refrigerator for 7 days at -5 C. Then each bottle was taken out from the refrigerator, and kept for about 30 minutes at room temperature. After that, it was observedwhether solid substance existed or not in the bottom of the bottle. There were no solid substance in each of them, and each of them was clear and uniform solution.</p>
<p>Preparation Example 3-6 Diflufenican(purity 93.2 %, 3.72 g as active ingredient), bromoxynhl=octanOate(pUrity94.8%, 16.74 gas active ingredient), ioxynil=octanoate(purity 96 %, 9.35 g as active ingredient), calcium dodecyl benzene sulfonate (5.00 g), polyoxyethylene tristyrylphenylether(HLB 12. 6; 4. OOg), sorbitanmonooleate(HLB 4.3; 1.00 g), aromatic hydrocarbon(include Cli to C14 alkylnaphthalene, Solvesso 200 ND, produced by Exxon Mobil Chemical Company; 10.00 g) and N-methyl-2-pyrrolidone(5.70 g) are measured in a 100 ml graduated flask. Then diethyl oxalate is added until the total amount being 100 ml. It is stirred until uniform solution to give the emulsifiable concentrate of the present invention.</p>
<p>Preparation Example 3-7 Diflufenican(purity 93.2 %, 3.72 gas active ingredient), bromoxynil=octanoate(purity94.8%, 16.74 gas active ingredient), ioxynil=octanoate(purity 96 %, 9.35 g as active ingredient), calcium dodecyl benzene sulfonate (5.00 g), polyoxyethylene tristyryl phenyl ether(HLB 12.6; 4.00 g), sorbitan mono laurate(HLB 8.6; 1.00 g), aromatic hydrocarbon(include Cli to C14 alkylnaphtha]ene, Solvesso 200 ND, produced by Exxon Mobil Chemical Company; 10.00 g) and N-methyl-2-pyrrolidone(5.70 g) are measured in a 100 ritl graduated flask. Then diethyl oxalate is added until the total amount being 100 ml. It is stirred until uniform solution to give the emulsifiable concentrate of the present invention.</p>
<p>Preparation Example 3-8 Diflufenican(purity 93.2 %, 3.72 gas active ingredient), bromoxynil=octanoate(purity 94.8%, 16.74 gas active ingredient), ioxynil=octanoate(purity 96 %, 9.35 g as active ingredient), calcium dodecyl benzene sulfonate (5.00 g), polyoxyethylene tristyryl phenyl ether(HLB 12.6; 4.00 g), sorbitan mono laurate(HLB 8.6; 1.00 g), aromatic hydrocarbon(include Cli to C14 alkylnaphthalene, Solvesso 200 ND, produced by Exxon Mobil Chemical Company; 12.00 g) and N,N-dimethylacetamide(5.70 g) are measured in a 100 ml graduated flask. Then diethyl oxalate is added until the total amount being 100 ml. It is stirred until uniform solution to give the emulsifiable concentrate of the present invention.</p>
<p>Preparation Example 3-9 Diflufenican(purity 93.2 %, 3.72 g as active ingredient), bromoxynil=octanoate(purity94.8%, 16.74 gas activeingredient), ioxynil=octanoate(purity 96 %, 9.35 g as active ingredient), calcium dodecyl benzene sulfonate (5.00 g), polyoxyethylene casteroil(HLB13.5; 4.OOg), sorbitanmonolaurate(HLB8.6; 1.00 g), aromatic hydrocarbon(include Cli to Cl4 alkylnaphthalene, Solvesso 200 ND, produced by Exxon Mobil Chemical Company; 12.00 g) and N-methyl-2-pyrrolidone(5.70 g) are measured in a 100 ml graduated flask. Then diethyl oxalate is added until the total amount being 100 ml. It is stirred until uniform solution to give the emulsifiable concentrate of the present invention.</p>
<p>Preparation Example 3-10 Diflufenican(purity 93.2 %, 3.72 gas active ingredient), bromoxynil=octanoate(purity94. 8%, 16.74 gas active ingredient).</p>
<p>ioxynil=octanoate(purity 96 %, 9.35 g as active ingredient), calcium dodecyl benzene sulfonate (5.00 g), sorbitan mono laurate(HLB 8.6; 5.00 g), aromatic hydrocarbon(include Cii to C14 alkylnaphthalene, SoJ.vesso 200 ND, produced by Exxon Mobil Chemical Company; 12.00 g) and 1,3-dimethyl-2-imidazolidinone(5.7 g) are measured in a 100 ml graduated flask. Then diethyl oxalate is added until the total amount being 100 ml. It is stirred until uniform solution to give the emulsifiable concentrate of the present invention.</p>
<p>Preparation Example 3-11 Diflufenican(purity 93.2 %, 3.72 gas active ingredient), calcium dodecyl benzene sulfonate (5.00 g), polyoxyethylene tristyryl phenyl ether(HLB 12.6; 4.00 g), sorbitan mono laurate(HLB 8.6; 1.00 g), aromatic hydrocarbon(include Cli to C14 alkylnaphthalene, Solvesso 200 ND, produced by Exxon Mobil Chemical Company; 12.00 g) and N-methyl-2-pyrrolidOfle(5. 70 g) are measured in a 100 ml graduated flask. Then diethyl oxalate is added until the total amount being ml. It is stirred until uniform solution to give the emulsifiable concentrate of the present invention.</p>
<p>Preparation Example 4-1 Diflufenicafl(4.O0 g as active ingredient), bromoxynil=octanoate(18.OO g as active ingredient), ioxynil=octanoate(l0.05 gas active ingredient), calciurndodecyl benzene sulfonate (3.20 g), butylpolyalkyleneoxide block copolymer(Toximul 8320, produced by Stepan; 4.80 g), aromatic hydrocarbon(include Cli to C14 alkylnaphthalene, Solvesso 200 ND, produced by Exxon Mobil Chemical Company; 5.00 g) 1, 3-dimethyl-2-imidaZoliZinOfle( 15.00 g) and N-methyl-2-pyrrolidOne(5. 50g)weremeasuredifla loomlgraduated flask. Then diethyl oxalate was added until the total amount being 100 ml. It was stirred until uniform solution to give the emulsifiable concentrate of the present invention(referred as the emulsifiable concentrate of the present invention 4-1, hereinafter).</p>
<p>Preparation Example 4-2 Diflufenican(4.00 g as active ingredient), bromoxynil=octanoate(18.00 g as active ingredient), ioxynil=octanoate(10.05 gas active ingredient), calcium dodecyl benzene sulfonate (3.20 g), polyalkyleneoxide block copolymer(Toximul 6323, produced by Stepan; 4.80 g), aromatic hydrocarbon(include Cli to C14 alkylnaphthalene, Solvesso 200 ND, produced by Exxon Mobil Chemical Company; 5.00 g) 1, 3-dirnethyl-2-imidazolizinOfle(15.00 g) and N-methyl-2-pyrrolidone( 5.50 g) weremeasuredin a 100 ml graduated flask. Then diethyl oxalate was added until the total amount being 100 ml. It was stirred until uniform solution to give the emulsifiable concentrate of the present invention(referred as the emulsifiable concentrate of the present invention 4-2, hereinafter).</p>
<p>Preparation Example 4-3 Diflufenican(4.00 g as active ingredient), bromoxynil=octanoate(18.00 g as active ingredient), ioxynil=octanoate(i0.05 gas active ingredient), calcium dodecyl benzene sulfonate (3.20 g), polya.lkyleneoxide block copolymer(Step-Flow 26, produced by Stepan; 4.80 g), aromatic hydrocarbon(include Cii to C14 alkylnaphthalene, Solvesso 200 ND, produced by Exxon Mobil Chemical Company; 5.00 g) i,3-dimethyl-2-imidaZoliZinOfle(15.00 g) and N-methyl-2-pyrrolidOfle( 5.50 g) weremeasuredina iOOml graduated flask. Then diethyl oxalate was added until the total amount being 100 ml. It was stirred until uniform solution to give the emulsifiable concentrate of the present invention(referred as the emulsifiable concentrate of the present invention 4-3, hereinafter).</p>
<p>Preparation Example 4-4 Diflufenican(4.0O g as active ingredient), bromoxynil=octanoate(18.00 g as active ingredient), ioxynil=octanoate(10.05 gas active ingredient), calcium dodecyl benzene sulfonate (3.20 g), polyalkyleneoxide block copolymer(Ethyla.n NS 500 LQ, produced by Akzo Nobel; 4.80 g)., aromatic hydrocarbon(include Cli to C14 alkylnaphthalene, Solvesso 200 ND, produced by Exxon Mobil Chemical Company; 5.00 g) i,3-dimethyl-2-imidazoliziflOfle(15.00 g) and N-mathyl-2-pyrrolidone(5.50 g) weremeasuredinalOOmigraduated flask. Then diethyl oxalate was added until the total amount being 100 ml. It was stirred until uniform solution to give the emulsifiable concentrate of the present invention(referred as the emulsifiable concentrate of the present invention 4-4, hereinafter).</p>
<p>Test Example 4-1</p>
<p>Into a iOOml-graduatedcylinderwith stopper. 98m1 of CIPAC standard water D (342ppm) were charged. The graduated cylinder was put in a thermostat and was kept at 30 C for awhile. Further, 2 ml each of the emulsifiable concentrate of the present invention 4-1 to 4-4 were added into the graduated cylinder, and the cylinder was turned upside down 10 times at a rate of once per two seconds.</p>
<p>Then, it was put in a thermostat again and left at 30 C for 2 hours. After that, each of the state of the emulsion in the graduated cylinder was observed. Each was provided uniform emulsion state. 1 69</p>
<p>INDUSTRIAL APPLICABILITY</p>
<p>The emulsifiable concentrate of the present invention is useful as pesticide formulation because it has an excellent stability of the emulsion even after diluted with water. o</p>
Claims (1)
- <p>CLAIMS</p><p>1. An emulsifiable concentrate comprising 2',4'difluoro2(a,a,a-trifluoro-m-tOlYlOXY)rnCOti.flaflhlide, 1,3-dimethyl-2-imidazolidiflOfle, an aromatic hydrocarbon; and a surfactant.</p><p>2. An emulsifiable concentrate according to claim 1, which comprises from I to 40% by weight of the aromatic hydrocarbon.</p><p>3. An emulsifiable concentrate according to claim I or 2, which comprises from 5 to 60% by weight of l,3-dimethyl-2-itnidazolidinone.</p><p>4. An emulsifiable concentrate according to any one of claims 1 to 3, wherein the surfactant comprises an anionic surfactant and a nonionic surfactant and the ratio by weight of the anionic surfactant to the nonionic surfactant is from 1:0.1 to 1:10.</p><p>5. An emulsifiable concentrate according to claim 4, wherein the anionic surfactant is an alkylbenzenesulfomc acid salt.</p><p>6. An emulsifiable concentrate according to claim 4 or 5, wherein the nonionic surfactant has polyalkylene oxide structure in the molecule.</p><p>7. An emulsifiable concentrate according to claim 6, wherein the nonionic surfactant is selected from polyoxyethylene-polyoxypropylene tristyiyl phenyl ether, polyoxyethylene Iristyryl phenyl ether and polyoxyethylene castor oil.</p><p>8. An emulsifiable concentrate according to claim 4 or 5, wherein the nonionic surfactant is a sorbitan fatty acid ester.</p><p>9. An emulsifiable concentrate according to any one of claims I to 8, comprising: 1 to 5 % by weight of to 60 % by weight of I,3-dimethyl-2-imidazolidinone; to 50 % by weight of an aromatic hydrocarbon; and 4 to 20 % by weight of a surfactant.</p><p>10. An emulsifiable concentrate according to any one of claims ito 9, which further comprises 4-cyano-2,6-dibromophenyl octanoate and 4-cyano-2,6-diiodophenyl octanoate.</p><p>11. An emulsifiable concentrate according to claim 10, which comprises from 1 to 30% by weight of 4-cyano-2,6-dibromophenyi octanoate and from 1 to 30% by weight of 4-cyano-2,6-diiodophenyl octanoate.</p><p>12. An aqueous composition which is obtainable by diluting an emulsifiable concentrate according to any one of claims 1 to 11 with water.</p><p>13. An emulsifiable concentrate according to claim 1 substantially as hereinbefore described in any one of the Preparation Examples.</p><p>14. An aqueous composition according to claim 12 substantially as herembefore described in any one of the Test Examples.</p>
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| GB0704016A GB2433030B (en) | 2005-03-31 | 2006-03-28 | Emulsifiable concentrate |
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| Application Number | Priority Date | Filing Date | Title |
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| JP2005101694 | 2005-03-31 | ||
| JP2005275323A JP2006306830A (en) | 2005-03-31 | 2005-09-22 | Agricultural chemical composition |
| JP2005281349A JP2007091619A (en) | 2005-09-28 | 2005-09-28 | Emulsifiable concentrate of herbicidally active compound |
| JP2005286832A JP2007091691A (en) | 2005-09-30 | 2005-09-30 | Agrochemical emulsifiable concentrate |
| GB0704016A GB2433030B (en) | 2005-03-31 | 2006-03-28 | Emulsifiable concentrate |
| GB0606184A GB2425955B (en) | 2005-03-31 | 2006-03-28 | Emulsifiable concentrate |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US20020086808A1 (en) * | 2000-10-02 | 2002-07-04 | Peter-Roger Nyssen | Active compound-containing emulsions |
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| US20020086808A1 (en) * | 2000-10-02 | 2002-07-04 | Peter-Roger Nyssen | Active compound-containing emulsions |
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