GB2424583A - Emulsifiable concentrate - Google Patents
Emulsifiable concentrate Download PDFInfo
- Publication number
- GB2424583A GB2424583A GB0606182A GB0606182A GB2424583A GB 2424583 A GB2424583 A GB 2424583A GB 0606182 A GB0606182 A GB 0606182A GB 0606182 A GB0606182 A GB 0606182A GB 2424583 A GB2424583 A GB 2424583A
- Authority
- GB
- United Kingdom
- Prior art keywords
- weight
- octanoate
- emulsifiable concentrate
- surfactant
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000004495 emulsifiable concentrate Substances 0.000 title claims abstract description 119
- 239000004094 surface-active agent Substances 0.000 claims abstract description 81
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- 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 13
- 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 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 11
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 11
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims abstract description 11
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims abstract description 10
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 claims description 135
- -1 Irimethylene group Chemical group 0.000 claims description 80
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 62
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical class CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 40
- 239000003945 anionic surfactant Substances 0.000 claims description 21
- 239000002736 nonionic surfactant Substances 0.000 claims description 21
- UYAAVKFHBMJOJZ-UHFFFAOYSA-N diimidazo[1,3-b:1',3'-e]pyrazine-5,10-dione Chemical compound O=C1C2=CN=CN2C(=O)C2=CN=CN12 UYAAVKFHBMJOJZ-UHFFFAOYSA-N 0.000 claims description 19
- 229940116423 propylene glycol diacetate Drugs 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 239000004359 castor oil Substances 0.000 claims description 9
- 235000019438 castor oil Nutrition 0.000 claims description 9
- 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 9
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 claims description 4
- DSVGICPKBRQDDX-UHFFFAOYSA-N 1,3-diacetoxypropane Chemical compound CC(=O)OCCCOC(C)=O DSVGICPKBRQDDX-UHFFFAOYSA-N 0.000 claims description 3
- KFNABOVSAPCOCY-UHFFFAOYSA-N 1-propanoyloxypropan-2-yl propanoate Chemical compound CCC(=O)OCC(C)OC(=O)CC KFNABOVSAPCOCY-UHFFFAOYSA-N 0.000 claims description 3
- SFTRWCBAYKQWCS-UHFFFAOYSA-N 2-butanoyloxyethyl butanoate Chemical compound CCCC(=O)OCCOC(=O)CCC SFTRWCBAYKQWCS-UHFFFAOYSA-N 0.000 claims description 3
- UMNVUZRZKPVECS-UHFFFAOYSA-N 2-propanoyloxyethyl propanoate Chemical compound CCC(=O)OCCOC(=O)CC UMNVUZRZKPVECS-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 238000007865 diluting Methods 0.000 claims description 2
- 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 10
- 239000012141 concentrate Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 description 128
- 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 60
- 239000005489 Bromoxynil Substances 0.000 description 60
- 239000005507 Diflufenican Substances 0.000 description 53
- WYEHFWKAOXOVJD-UHFFFAOYSA-N diflufenican Chemical compound FC1=CC(F)=CC=C1NC(=O)C1=CC=CN=C1OC1=CC=CC(C(F)(F)F)=C1 WYEHFWKAOXOVJD-UHFFFAOYSA-N 0.000 description 53
- NRXQIUSYPAHGNM-UHFFFAOYSA-N ioxynil Chemical compound OC1=C(I)C=C(C#N)C=C1I NRXQIUSYPAHGNM-UHFFFAOYSA-N 0.000 description 52
- 239000003921 oil Substances 0.000 description 36
- 235000019198 oils Nutrition 0.000 description 36
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 11
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 10
- 239000000126 substance Substances 0.000 description 9
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 description 8
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 8
- 241000219357 Cactaceae Species 0.000 description 8
- 150000004996 alkyl benzenes Chemical class 0.000 description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 7
- 229930195729 fatty acid Natural products 0.000 description 7
- 239000000194 fatty acid Substances 0.000 description 7
- 229910019142 PO4 Inorganic materials 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 239000010452 phosphate Substances 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 235000015112 vegetable and seed oil Nutrition 0.000 description 5
- 239000008158 vegetable oil Substances 0.000 description 5
- 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
- 150000001346 alkyl aryl ethers Chemical class 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
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000005215 alkyl ethers Chemical class 0.000 description 3
- 230000002363 herbicidal effect Effects 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
- 229920000642 polymer Polymers 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000001149 (9Z,12Z)-octadeca-9,12-dienoate Substances 0.000 description 2
- UBLAMKHIFZBBSS-UHFFFAOYSA-N 3-Methylbutyl pentanoate Chemical compound CCCCC(=O)OCCC(C)C UBLAMKHIFZBBSS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-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
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-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
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 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
- 229920000090 poly(aryl ether) Polymers 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
- 238000003756 stirring Methods 0.000 description 2
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 2
- IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical compound CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- WTTJVINHCBCLGX-UHFFFAOYSA-N (9trans,12cis)-methyl linoleate Natural products CCCCCC=CCC=CCCCCCCCC(=O)OC WTTJVINHCBCLGX-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
- 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
- VLODCNGYDDGPFG-UHFFFAOYSA-N 2,3-dimethyl-1-propan-2-ylnaphthalene Chemical compound C1=CC=C2C(C(C)C)=C(C)C(C)=CC2=C1 VLODCNGYDDGPFG-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
- 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
- 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
- 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
- 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
- PKIXXJPMNDDDOS-UHFFFAOYSA-N Methyl linoleate Natural products CCCCC=CCCC=CCCCCCCCC(=O)OC PKIXXJPMNDDDOS-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 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
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003086 colorant Substances 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
- 150000004665 fatty acids Chemical class 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
- 229940094941 isoamyl butyrate Drugs 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
- 239000007788 liquid Substances 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
- 229940038384 octadecane Drugs 0.000 description 1
- GXOHBWLPQHTYPF-UHFFFAOYSA-N pentyl 2-hydroxypropanoate Chemical compound CCCCCOC(=O)C(C)O GXOHBWLPQHTYPF-UHFFFAOYSA-N 0.000 description 1
- 230000000361 pesticidal effect Effects 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
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 239000008234 soft water Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives 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
- 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)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
An emulsifiable concentrate comprising: 2',4'-difluoro-2-(a,a,a-trifluoro-m-tolyloxy)nicotinanilide; a compound of formula (1): <EMI ID=1.1 HE=22 WI=61 LX=738 LY=921 TI=CF> <PC>wherein R<1> and R<2> independently represent alkyl groups, A represents ethylene group, trimethylene group, propylene group or tetramethylene group, and the sum of the number of carbon atoms contained by the groups R<1>, R<2> and A is from 4 to 10; an aromatic hydrocarbon; and a surfactant. The concentrate may also comprise 4-cyano-2,6-dibromophenyl octanoate and 4-cyano-2,6-diiodophenyl octanoate.
Description
EMULSIFIABLE CONCENTRATE
FIELD OF THE INVENTION
The present invention relates to a pesticidal emulsifiable concentrate which contains 2' ,4' -difluoro-2--(a,a,a-trifluoro-m-tolyloxy)nicotinanilide as a herbicidal active ingredient.
BACKGROUND ART
It is known that 2' ,4' -difluoro-2-(a,a,a-trifluoro-m-tolyloxy)nicotinanilide shown by the below formula is an active ingredient of herbicide in USP-4618366. CF3
O
DISCLOSURE OF THE INVENTION
The present invention provides an emulsifiable concentrate containing 2' ,4' -difluoro-2-(a,a,a-trifluoro-.m-tolyloxy)nicotinanilide as aherbicidal active ingredient which has an excellent stability of the emulsion even after diluted with water.
According to the present invention, an emulsifiable concentrate containing the compound shown by the formula (1): R1OOR2 (1) wherein, in the formula, R1 and R2 represent alkyl groups, A represents ethylene group, trimethylene group, propylene group or tetramethylene group, and the sum of the number of carbon atoms which consist of the groups of R1, R2 and A is 4 to 10; and an aromatic hydrocarbon as solvent and a surfactant and 2' ,4' -difluoro-2-(a,a,a-trifluoro-m-tolyloxy)nicotinanilide has an excellent stability of the emulsion even after diluted with water.
Namely, the present invention is as follows: [1] An emulsifiable concentrate comprising 2' ,4' -difluoro-2-(a,a,a-trifluoro--m--tolyloxy)nicotinanilide the compound shown by the below formula (1): R1OOR2 (1) wherein, in the formula, R1 and R2 represent alkyl groups, A represents ethylene group, trimethylene group, propylene group or tetramethylene group, and the sum of the number of carbon atoms which consist of the groups of R1, R2 and A is 4 to 10; an aromatic hydrocarbon and a surfactant.
[2] An emulsifiable concentrate comprising 2' ,4' -difluoro-2-(a,a,a--trifluoro-m-tolyloxy)nicotinanilide 4-cyano-2, 6-dibromophenyl octanoate; 4-cyano-2, 6-diiodophenyl octanoate; the compound shown by the below formula (1): o 0 II II (1)
A
R1 OO R2 wherein, in the formula, R1 and R2 represent alkyl groups, A represents ethylene group, trimethylene group, propylene group or tetramethylene group, and the sum of the number of carbon atoms which consist of the groups of R', R2 and A is 4 to 10; an aromatic hydrocarbon and a surfactant.
[3] An emulsifiable concentrate comprising 1 to 5 % by weight of 2' ,4'-difluoro-2-(a,a,a-trifluoro-m-tolyloxy)nicotinanjlide 1 to 30 % by weight of 4-cyano-2,6-dibromophenyl octanoate; 1 to 30 % by weight of 4-cyano-2,6-diiodophenyl octanoate; to 80 % by weight of the compound shown by the below formula (1): 0 0 1 II (1)
A
R1 OO R wherein, in the formula, R1 and R2 represent alkyl groups, A represents ethylene group, trimethylene group, propylene group or tetramethylene group, and the sum of the number of carbon atoms which consist of the groups of R1, R2 and A is 4 to 10; an aromatic hydrocarbon and 4 to 20 % by weight of a surfactant; and the total content of 4-cyano-2,6- dibromophenyl octanoate, 4-cyano-2, 6-dilodophenyl octanoate and the aromatic hydrocarbon in the emulsifiable concentrate is 15 to 80 % by weight.
[4] The emulsifiable concentrate according to [3], wherein the emulsifiable concentrate is essentially consisting of 1 to 5 % by weight of 2' ,4'-difluoro-2-(a,a,a-trifluoro-m-tolyloxy)nicotinanilide 1 to 30 % by weight of 4-cyano-2,6-dibromophenyl octanoate; 1 to 30 % by weight of 4-cyano-2,6-diiodophenyl octanoate; to 80 % by weight of the compound shown by the below formula (1): 0 0 1 II (1) R1OO'R2 wherein, in the formula, R' and R2 represent alkyl groups, A represents ethylene group, trimethylene group, propylene group or tetramethylene group, and the sum of the number of carbon atoms which consist of the groups of R', R2 and A is 4 to 10; an aromatic hydrocarbon and 4 to 20 % by weight of a surfactant; and the total content of 4-cyano-2,6- dibromophenyl octanoate, 4-cyano-2, 6-diiodophenyl octanoate and the aromatic hydrocarbon in the emulsifiable concentrate is 15 to 80 % by weight.
[5] The emulsifiable concentrate according to any one of [1] to [4], wherein the amount of the compound shown by the formula (1) is in the range between 5 and 80 by weight per 1 part by weight of 2' ,4'-difluoro-2-(a,a,a-trifluoro-m-tolyloxy)nicotinanilide [6] The emulsifiable concentrate according to any one of [1] to [5] , wherein the surfactant is amixture of 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.
[7] The emulsifiable concentrate according to any one of [1] to [5], wherein the surfactant is a mixture of dodecyl benzene sulfonic acid salt and polyoxyethylene castor oil; and the ratio by weight of the dodecyl benzene sulfonic acid salt and the polyoxyethylene castor oil is 1:0.1 to 1:10.
[8] The emulsifiable concentrate according to any one of [1] to [7], wherein the compound shown by the formula (1) is the compound selected from the group consisting of ethylene glycol diacetate, ethylene glycol dipropionate, ethylene glycol dibutyrate, propylene glycol diacetate, propylene glycol dipropionate and 1,3-propanediol diacetate.
[9] An aqueous composition which is obtainable by diluting the emulsifiable concentrate according to any one of [1] to [8] with water.
The emulsifiable concentrate of the present invention comprises 2' ,4' -difluoro-2-(a,a,a-trifluoro-m-tolyloxy)nicotinaniljde the compound shown by the below formula (1): R1OOR2 (1); an aromatic hydrocarbon and a surfactant.
2' ,4' -difluoro-2-(a,a,a-trifluoro-m-tolyloxy)nicotina nilide is the compound named diflufenican as common name (referred as diflufenicari hereinafter).
The emulsifiable concentrate of the present invention usually contains 4cyano-2,6-dibromopheny3. octanoate and 4-cyano-2,6-diiodophenyl octanoate as herbicidal active ingredients. 4- cyano-2,6-dibromophenyl octanoate is the compound named bromoxynil octanoate as common name(referred as bromoxynil=octanoate, hereinafter).
4-cyano--2, 6-diiodophenyloctanoate is the compound named ioxynil octanoate as common name(ref erred as ioxynil=octanoate, hereinafter).
Diflufenican is the compound disclosed in "The Pesticide 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 inUSP-4618366. Bromoxynil=octanoate is the compound disclosed in "The PesticideManual" (mentionedabove) as reference number 95. It is a solid compound and its melting point is about to 46 C. 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.
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.
In the emulsifiable concentrate of the present invention, the total amount 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. The amount of diflufenican is usually 1 to 5 % by weight based on the total weight of the emulsifiable concentrate of the present invention, the amount of bromoxynil=octanoate is usually 1 to 30 % by weight based on the total weight of emulsifiable concentrate of the present invention; and the amount of ioxynil=octanoate is usually 1 to 30 % by weight based on the total weight of the emulsifiable concentrate of the present invention. Preferably, the amount of diflufenican is 1 to 4 % by weight, bromoxynyl=octanoate is 6 to 20 % by weight, ioxynyl=octanoate is 4 to 12 % by weight based on the total weight of the emulsifiable concentrate of the present invention. More preferably, the amount of diflufenican is 1.5 to 4 % by weight, bromoxynyl=octanoate is 8 to 18 % by weight, ioxynyl=octanoate is 4 to 10 % by weight based on the total weight of the emulsifiable concentrate of the present invention.
The emulsifiable concentrate of the present invention contains the compound shown by the formula (1)(referred as the present solvent 1, hereinafter) as a solvent.
In the formula (1), A represents ethylene group, trimethylene group, propylene group or tetramethylene group.
In the formula (1), each of R1 and R2 independently represents alkyl group such as Cl to C4 alkyl group include methyl group, ethyl group, isopropyl group and 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 4 to 10, preferably 4 to 8.
Examples of the present solvent 1 include ethylene glycol diacetate, ethylene glycol dipropionate, ethylene glycol dibutyrate, propylene glycol diacetate, propylene glycol dipropionate and 1,3-propanediol diacetate. The present solventcanbeusedbyitselformixtureofabovementionedcompound.
For the emulsifiable concentrate of the present invention, ethylene glycol diacetate or propylene glycol diacetete is preferably used.
The amount of the present solvent 1 is usually 5 to 80 % by weight, preferably 20 to 70 % by weight based on the total weight of the emulsifiable concentrate of the present invention.
And the amount of the present solvent 1 is preferably 5 to 80 by weight, more preferably 8 to 80 by weight, far more preferably to 50 % by weight based on the weight of diflufenican.
The emulsifiable concentrate of the present invention further includes an aromatic hydrocarbon. In the present invention, aromatic hydrocarbon means an aromatic hydrocarbon compound which is a liquid at room temperature(25 C). The aromatic hydrocarbon(ref erred as the present solvent 2, hereinafter) includes alkylbenzene(for example, xylene, tetramethylbenzene and the like), alkylnaphthalene(f or example, methylnaphthalene), diphenylethane, dixylylethane, phenyixylylethane and the mixture thereof.
Concretely, the 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-ethylphenylethane), 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 dimethylnaphthalene), Cactus Solvent P-100 (commercial name of Nikko Petrochemical Company, alkylbenzene having 9 to 10 carbon atoms), Cactus Solvent P-150 (commercial name of Nikko Petrochemical Company, alkylbenzene), Cactus Solvent P-180 (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, dimethylmonoisopropylnaphthalene), Solvesso 100 (commercial name of Exxon Chemical Corp., aromatic hydrocarbon, mainly C9 to ClO dialkyl and trialkyl benzene), Solvesso 150 (commercial name of Exxon Chemical Corp., aromatic hydrocarbon, mainly ClO to Cii alkylbenzene), Solvesso 150 ND (commercial name of Exxon Mobil Chemical Company, aromatic hydrocarbon, mainly ClO to Cii alkylbenzene), Solvesso 200 (commercial name of Exxon Chemical Corp. , 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 alkylnaphthalene), Suwasol 100 (commercial name of Maruzen Petrochemical Company, toluene) and Suwasol 200 (commercial name of Maruzen Petrochemical Company, xylene) can be used as the present solvent 2.
In the emulsifiable concentrate of the present invention, the total amount of bromoxynil=octanoate, ioxynil=octanoate and the present solvent 2 is usually 15 to 80 % by weight based on the total weight of the emulsifiable concentrate of the present invention.
The emulsifiable concentrate of the present invention contains a surf actant. The surf act ant used for the emulsifiable concentrate of the present invention is preferably a mixture of an anionic surfactant and a nonionic surfactant.
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 polyoxyethylene 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 polyoxyethylenealkyl phosphate ester.
Generally, sodium salt, calcium salt and ammonium salt are exemplified as sulfonic acid salt, sulfate salt or phosphate salt.
Preferably alkyl aryl sulfonic acid salt, especially dodecyl benzene sulfonic acid salt such as sodium salt and calcium salt is used for the emulsifiable concentrate of the present invention.
Commercially available surfactant such as Rhodacal 70, Rhodacal7o/B and Rhodacal6o/BE(each produced by Rhodia Nicca) 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 surfactant such as Rhodafac MB(produced by Rhodia Nicca) can be used as polyoxyethylenealkyl phosphate ester.
Examples of nonionic surfactant include polyoxyethylene -polyoxypropylene block polymer; fatty acid ester of polyoxyethylene-polyoxypropylene block polymer; polyoxyethylene-polyoxypropylene alkyl ether; polyoxyethylenepolyoxypropylene polyaryl ether polyoxyethylene-polyoxypropylene alkyl aryl ether; polyoxyethylene alkyl aryl ether; polyoxyethylene polyaryl ether; polyoxyethylene vegetable oil such as polyoxyethylene castor oil and the like; polyoxyethylene hardened vegetable oil such as polyoxyethylene hardened castor oil and the like; polyoxyethylenepolyoxypropylene vegetable oil such as polyoxyethylene-polyoxypropylene castor oil and the like; polyoxyethylene fatty acid esters; polyoxyethylene alkyl ether; polyoxyethylene tristyryl pheny.l phosphate diester; polyoxyethylene-polyoxypropylene tristyryl phenyl phosphate diester; fatty acid alcohol polyglycol ether; and fatty acid ester of glycerin.
Preferable examples include polyoxyethylene vegetable oil, polyoxyethylene hardened vegetable oil, polyoxyethylene alkyl aryl ether, polyoxyethylene tristyryl phenyl phosphate diester and polyoxyethylene- polyoxypropylene tristyryl phenyl phosphate diester, especially include polyoxyethylene castor oil.
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 surf actant such as Solpol T26 (produced by Toho Chemical Industry) can be used as polyoxyethylene alkyl aryl ether.
Commerciallyavailablesurfactant suchasAlkamulsOR4o, Alkamuls BR(each produced by Rhodia Nicca) can be used as polyoxyethylene castor oil. Commercially available surfactant such as Newcol 150(produced by Nippon Nyukazai) can be used as polyoxyethylene fatty acid ester. Commercially 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 PIOMIN D-900 series(produced by TAKEMOTO Oil & Fat) can be used as fatty acid ester of glycerin.
In the emulsifiable concentrate of the present invention, the amount of surf actant 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 is a mixture of an anionic surfact ant and a nonionic surfact ant, the weight ratio of the anionic surfactant and the nonionic surfactant is 1:0. 1 to 1: 10 and the amount of anionic surfactant and nonionic surfactant is preferably 2 to 5 % each by weight based on the total weight of the emulsifiable concentrate of the present invention.
In the emulsifiable concentrate of the present invention, when a mixture of an anionic surfactant and a nonionic surf act ant is used as a surfactant, the mixture of dodecyl benzene sulfonic acid salt and polyoxyethylene caster oil is preferably used.
Besides (a) diflufenican, (b) bromoxynil=octanoate, (c)ioxynil=octanoate, (d)the present solvent 1, (e)the present solvent 2 and (f)a surfactant; the emulsifiable concentrate of the present invention may contain another organic solvent, an additive and the like if necessary.
Another organic solvent includes monoester solvents such as methyl laurate, isopropyl myristate, isopropyl palmitate, methylcaprate, methyloleate, isobutyloleate, butylpropionate, isoamyl propionate, ethyl butyrate, butyl butyrate, isoamyl butyrate, isoamyl valerate, amyl lactate, methyl linoleate, methyl linolenate, palm fatty acid methyl and the like; aliphatic hydrocarbon solvents such as decane, tridecane, tetradecane, hexadecane, octadecane and the like.
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.
The embodiments of the present invention will be explained below.
An emulsifiable concentrate comprising 1 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 5 to 80 % by weight of the present solvent 1; the present solvent 2 and 4 to 20 % by weight of a surfactant; and the total content of bromoxynil=octanoate, ioxynil=octanoate and the present solvent 2 in the emulsifiable concentrate is to 80 % by weight.
An emulsifiable concentrate essentially consisting of 1 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; to 80 % by weight of the present solvent 1; the present solvent 2 and 4 to 20 % by weight of a surfactant; and the total content of bromoxynil=octanoate, ioxynhl=octanoate and the present solvent 2 in the emulsifiable concentrate is 15 to 80 % by weight.
An emulsifiable concentrate comprising 1 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynhl=octanoate; 5 to 80 % by weight of the present solvent 1; the present solvent 2 and 4 to 20 % by weight of a surfactant; and the total content of bromoxynil=octanoate, ioxynil=octanoate and the present solvent 2 in the emulsifiable concentrate is to 80 % by weight; and the amount of the present solvent 1 is in the range between and 80 by weight per 1 pert by weight of diflufenican.
An emulsifiable concentrate essentially consisting of 1 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynhl=octanoate; to 80 % by weight of the present solvent 1; the present solvent 2 and 4 to 20 % by weight of a surfactant; and the total content of bromoxynil=octanoate, ioxynil=octanoate and the present solvent 2 in the emulsifiable concentrate is to 80 % by weight; and the amount of the present solvent 1 is in the range between and 80 by weight per 1 pert by weight of diflufenican.
An emulsifiable concentrate comprising 1 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 5 to 80 % by weight of the present solvent 1; the present solvent 2 and 4 to 20 % by weight of a surfactant; and the total content of bromoxynil=octanoate, ioxynil=octanoate and the present solvent 2 in the emulsifiable concentrate is to 80 % by weight; and the surfactant is a mixture of 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.
An emulsifiable concentrate essentially consisting of 1 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynhl=octanoate; to 80 % by weight of the present solvent 1; the present solvent 2 and 4 to 20 % by weight of a surfactant; and the total content of bromoxynil=octanoate, ioxynil=octanoate and the present solvent 2 in the emulsifiable concentrate is to 80 % by weight; and the surfactant is a mixture of an anionic surfactant and a nonionic surfactant; and the ratio by weight of the anionic surf act ant and the nonionic surfactant is 1:0. 1 to 1:10.
An emulsifiable concentrate comprising 1 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 5 to 80 % by weight of the present solvent 1; the present solvent 2 and 4 to 20 % by weight of a surfactant; and the total content of bromoxynil=octanoate, ioxynil=octanoate and the present solvent 2 in the emulsifiable concentrate is to 80 % by weight; and the amount of the present solvent 1 is in the range between and 80 by weight per 1 pert by weight of diflufenican; the surf act ant is a mixture of an anionic surf actant and a nonionic surfactant; and the ratio by weight of the anionic surfact ant and the nonionic surfactant is 1:0.1 to 1:10.
An emulsifiable concentrate essentially consisting of 1 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; to 80 % by weight of the present solvent 1; the present solvent 2 and 4 to 20 % by weight of a surfactant; and the total content of bromoxynil=octanoate, ioxynil=octanoate and the present solvent 2 in the emulsifiable concentrate is to 80 % by weight; and the amount of the present solvent 1 is in the range between 5 and 80 by weight per 1 pert by weight of diflufenican; the surfactant is a mixture of an anionic surfactant and a nonionic surf actant; and the ratio by weight of the anionic surfactant and the nonionic surfactant is 1:0.1 to 1:10.
An emulsifiable concentrate comprising 1 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 5 to 80 % by weight of the present solvent 1; the present solvent 2 and 4 to 20 % by weight of a surfactant; and the total content of brornoxynil=octanoate, ioxynil=octanoate and the present solvent 2 in the emulsifiable concentrate is to 80 % by weight; and the surfactant is a mixture of dodecyl benzene sulfonic acid salt and polyoxyethylene caster oil; and the ratio by weight of dodecyl benzene sulfonic acid salt and polyoxyethylene caster oil is 1:0.1 to 1:10.
An emulsifiable concentrate essentially consisting of 1 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; to 80 % by weight of the present solvent 1; the present solvent 2 and 4 to 20 % by weight of a surfactant; and the total content of bromoxynil=octanoate, ioxynil=octanoate and the present solvent 2 in the emulsifiable concentrate is to 80 % by weight; and the surfactant is a mixture of dodecyl benzene sulfonic acid salt and polyoxyethylene caster oil; and the ratio by weight of dodecyl benzene sulfonic acid salt and polyoxyethylene caster oil is 1:0.1 to 1:10.
An emulsifiable concentrate comprising 1 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynhl=octanoate; 1 to 30 % by weight of ioxynhl=octanoate; 5 to 80 % by weight of the present solvent 1; the present solvent 2 and 4 to 20 % by weight of a surfactant; and the total content of bromoxynil=octanoate, ioxynhl=octanoate and the present solvent 2 in the emulsifiable concentrate is to 80 % by weight; and the amount of the present solvent 1 is in the range between and 80 by weight per 1 pert by weight of diflufenican; the surfactant is a mixture of dodecyl benzene sulfonic acid salt and polyoxyethylene caster oil; and the ratio by weight of dodecyl benzene sulfonic acid salt and polyoxyethylene caster oil is 1:0. 1 to 1:10.
An emulsifiable concentrate essentially consisting of 1 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; to 80 % by weight of the present solvent 1; the present solvent 2 and 4 to 20 % by weight of a surfactant; and the total content of bromoxynil=octanoate, ioxynil=octanoate and the present solvent 2 in the emulsifiable concentrate is to 80 % by weight; and the amount of the present solvent 1 is in the range between 5 and 80 by weight per 1 pert by weight of diflufenican; the surfactant is a mixture of dodecyl benzene sulfonic acid salt and polyoxyethylene caster oil; and the ratio by weight of dodecyl benzene sulfonic acid salt and polyoxyethylene caster oil is 1:0.1 to 1:10.
An emulsifiable concentrate comprising 1 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 5 to 80 % by weight of the present solvent 1; the present solvent 2 and 4 to 20 % by weight of a surfactant; and the total content of bromoxynil=octanoate, ioxynil=octanoate and the present solvent 2 in the emulsifiable concentrate is to 80 % by weight; and the surfact ant is a mixture of dodecyl benzene sulfonic acid salt and polyoxyethylene caster oil; and the ratio by weight of dodecyl benzene sulfonic acid salt and polyoxyethylene caster oil is 1:0.1 to 1:10; and the solvent 1 is propylene glycol diacetate.
An emulsifiable concentrate essentially consisting of 1 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynhl=octanoate; 5 to 80 % by weight of the present solvent 1; the present solvent 2 and 4 to 20 % by weight of a surfactant; and the total content of bromoxynil=octanoate, ioxynil=octanoate and the present solvent 2 in the emulsifiable concentrate is to 80 % by weight; and the surfactant is a mixture of dodecyl benzene sulfonic acid salt and polyoxyethylene caster oil; and the ratio by weight of dodecyl benzene sulfonic acid salt and polyoxyethylene caster oil is 1:0.1 to 1:10; and the solvent 1 is propylene glycol diacetate.
An emulsifiable concentrate comprising 1 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 5 to 80 % by weight of the present solvent 1; the present solvent 2 and 4 to 20 % by weight of a surfactant; and the total content of bromoxynil=octanoate, ioxynil=octanoate and the present solvent 2 in the emulsifiable concentrate is to 80 % by weight; and the amount of the present solvent 1 is in the range between and 80 by weight per 1 pert by weight of diflufenican; the surfactant is a mixture of dodecyl benzene sulfonic acid salt and polyoxyethylene caster oil; and the ratio by weight of dodecyl benzene sulfonic acid salt and polyoxyethylene caster oil is 1:0. 1 to 1:10; and the solvent 1 is propylene glycol diacetate.
An emulsifiable concentrate essentially consisting of 1 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxyniloctanoate; 1 to 30 % by weight of ioxynil=octanoate; to 80 % by weight of the present solvent 1; the present solvent 2 and 4 to 20 % by weight of a surfactant; and the total content of bromoxynil=octanoate, ioxynhl=octanoate and the present solvent 2 in the emulsifiable concentrate is to 80 % by weight; and the amount of the present solvent 1 is in the range between and 80 by weightper 1 pert by weight of diflufenican; the surfactant is a mixture of dodecyl benzene sulfonic acid salt and polyoxyethylene caster oil; and the ratio by weight of dodecyl benzene sulfonic acid salt and polyoxyethylene caster oil is 1:0.1 to 1:10; and the solvent 1 is propylene glycol diacetate.
An emulsifiable concentrate comprising 1 to 4 % by weight of diflufenican; 6 to 20 % by weight of bromoxynil=octanoate; 4 to 12 % by weight of ioxynil=octanoate; 5 to 80 % by weight of the present solvent 1; the present solvent 2 and 4 to 20 % by weight of a surfactant; and the total content of bromoxynil=octanoate, ioxynil=octanoate and the present solvent 2 in the emulsifiable concentrate is to 80 % by weight; and the surfactant is a mixture of dodecyl benzene sulfonic acid salt and polyoxyethylene caster oil; and the ratio by weight of dodecyl benzene sulfonic acid salt and polyoxyethylene caster oil is 1:0.1 to 1:10; and the solvent 1 is propylene glycol diacetate.
An emulsifiable concentrate essentially consisting of 1 to 4 % by weight of diflufenican; 6 to 20 % by weight of bromoxynil=octanoate; 4 to 12 % by weight of ioxynil=octanoate; to 80 % by weight of the present solvent 1; the present solvent 2 and 4 to 20 % by weight of a surfactant; and the total content of bromoxynil=octanoate, ioxynil=octanoate and the present solvent 2 in the emulsifiable concentrate is to 80 % by weight; and the surfactant is a mixture of dodecyl benzene sulfonic acid salt and polyoxyethylene caster oil; and the ratio by weight of dodecyl benzene sulfonic acid salt and polyoxyethylene caster oil is 1:0.1 to 1:10; and the solvent 1 is propylene glycol diacetate.
An emulsifiable concentrate comprising 1 to 4 % by weight of diflufenican; 6 to 20 % by weight of bromoxynil=octanoate; 4 to 12 % by weight of ioxynil=octanoate; 5 to 80 % by weight of the present solvent 1; the present solvent 2 and 4 to 20 % by weight of a surfactant; and the total content of bromoxynil=octanoate, ioxynil=octanoate and the present solvent 2 in the emulsifiable concentrate is to 80 % by weight; and the amount of the present solvent 1 is in the range between and 80 by weight per 1 pert by weight of diflufenican; the surfactant is a mixture of dodecyl benzene sulfonic acid salt and polyoxyethylene caster oil; and the ratio by weight of dodecyl benzene sulfonic acid salt and polyoxyethylene caster oil is 1:0.1 to 1:10; and the solvent 1 is propylene glycol diacetate.
An emulsifiable concentrate essentially consisting of 1 to 4 % by weight of diflufenican; 6 to 20 % by weight of bromoxynil=octanoate; 4 to 12 % by weight of ioxynil=octanoate; to 80 % by weight of the present solvent 1; the present solvent 2 and 4 to 20 % by weight of a surfactant; and the total content of bromoxynil=octanoate, ioxynil=octanoate and the present solvent 2 in the emulsifiable concentrate is 15 to 80 % by weight; and the amount of the present solvent 1 is in the range between and 80 by weight per 1 pert by weight of diflufenican; the surfactant is a mixture of dodecyl benzene sulfonic acid salt and polyoxyethylene caster oil; and the ratio by weight of dodecyl benzene sulfonic acid salt and polyoxyethylene caster oil is 1:0.1 to 1:10; and the solvent 1 is propylene glycol diacetate.
An emulsifiable concentrate comprising 1.5 to 4 % by weight of diflufenican; 8 to 18 % by weight of bromoxynil=octanoate; 4 to 10 % by weight of ioxynhl=octanoate; 5 to 80 % by weight of the present solvent 1; the present solvent 2 and 4 to 20 % by weight of a surfactant; and the total content of bromoxynil=octanoate ioxynil=octanoate and the present solvent 2 in the emulsifiable concentrate is to 80 % by weight; and the surfactant is a mixture of dodecyl benzene sulfonic acid salt and polyoxyethylene caster oil; and the ratio by weight of dodecyl benzene sulfonic acid salt and polyoxyethylene caster oil is 1:0.1 to 1:10; and the solvent 1 is propylene glycol diacetate.
An emulsifiable concentrate essentially consisting of 1.5 to 4 % by weight of diflufenican; 8 to 18 % by weight of bromoxynil=octanoate; 4 to 10 % by weight of iOxynil=octanoate; to 80 % by weight of the present solvent 1; the present solvent 2 and 4 to 20 % by weight of a surfactant; and the total content of bromoxynil=octanoate, ioxynil=octanoate and the present solvent 2 in the emulsifiable concentrate is to 80 % by weight; and the surfactant is a mixture of dodecyl benzene sulfonic acid salt and polyoxyethylene caster oil; and the ratio by weight of dodecyl benzene sulfonic acid salt and polyoxyethylene caster oil is 1:0.1 to 1:10; and the solvent 1 is propylene glycol diacetate.
An emulsifiable concentrate comprising 1. 5 to 4 % by weight of diflufenican; 8 to 18 % by weight of bromoxynil=octanoate; 4 to 10 % by weight of ioxyniloctanoate; 5 to 80 % by weight of the present solvent 1; the present solvent 2 and 4 to 20 % by weight of a surfactant; and the total content of bromoxynhl=octanoate ioxynil=octanoate and the present solvent 2 in the emulsifiable concentrate is to 80 % by weight; and the amount of the present solvent 1 is in the range between 5 and 80 by weight per 1 pert by weight of diflufenican; the surfactant is a mixture of dodecyl benzene sulfonic acid salt and polyoxyethylene caster oil; and the ratio by weight of dodecyl benzene sulfonic acid salt and polyoxyethylene caster oil is 1:0.1 to 1:10; and the solvent 1 is propylene glycol diacetate.
An emulsifiable concentrate essentially consisting of 1.5 to 4 % by weight of diflufenican; 8 to 18 % by weight of bromoxynil=octanoate; 4 to 10 % by weight of ioxynil=octanoate; 5 to 80 % by weight of the present solvent 1; the present solvent 2 and 4 to 20 % by weight of a surfactant; and the total content of bromoxynil=octanoate, ioxynil=octanoate and the present solvent 2 in the emulsifiable concentrate is to 80 % by weight; and the amount of the present solvent 1 is in the range between and 80 by weight per 1 pert by weight of diflufenican; the surfactant is a mixture of dodecyl benzene sulfonic acid salt and polyoxyethylene caster oil; and the ratio by weight of dodecyl benzene sulfonic acid salt and polyoxyethylene caster oil is 1:0.1 to 1:10; and the solvent 1 is propylene glycol diacetate.
An emulsifiable concentrate essentially consisting of 1.5 to 4 % by weight of diflufenican; 8 to 18 % by weight of bromoxynil=octanoate; 4 to 10 % by weight of ioxynil=octanoate; to 50 % by weight of the present solvent 1; 4 to 20 % by weight of a surfactant and rest of the present solvent 2.
An emulsifiable concentrate essentially consisting of 1.5 to 4 % by weight of diflufenican; 8 to 18 % by weight of bromoxynil=octanoate; 4 to 10 % by weight of ioxynhl=octanoate; to 50 % by weight of the present solvent 1; 2 to 5 % by weight of an anionic surfactant; 2 to 5 % by weight of a nonionic surfactant and rest of the present solvent 2.
An emulsifiable concentrate essentially consisting of 1.5 to 4 % by weight of diflufenican; 8 to 18 % by weight of bromoxynil=octanoate; 4 to 10 % by weight of ioxynil=octanoate; to 50 % by weight of propylene glycol diacetate; 4 to 20 % by weight of a surfactant and rest of the present solvent 2.
An emulsifiable concentrate essentially consisting of 1.5 to 4 % by weight of diflufenican; 8 to 18 % by weight of bromoxynil=octanoate; 4 to 10 % by weight of ioxynil=octanoate; to 50 % by weight of propylene glycol diacetate; 2 to 5 % by weight of an anionic surfactant; 2 to 5 % by weight of a nonionic surfactant and rest of the present solvent 2.
An emulsifiable concentrate essentially consisting of 1.5 to 4 % by weight of diflufenican; 8 to 18 % by weight of bromoxynil=octanoate; 4 to 10 % by weight of ioxynil=octanoate; 30 to 50 % by weight of the present solvent 1; 2 to 5 % by weight of an anionic surfactant; 2 to 5 % by weight of a nonionic surfactant and rest of the present solvent 2.
An emulsifiable concentrate essentially consisting of 1.5 to 4 % by weight of diflufenican; 8 to 18 % by weight of bromoxynil=octanoate; 4 to 10 % by weight of ioxynil=octanoate; to 50 % by weight of propylene glycol diacetate; 2 to 5 % by weight of dodecyl benzene sulfonic acid salt; 2 to 5 % by weight of polyoxyethylene caster oil and rest of the present solvent 2.
The emulsifiable concentrate of the present invention can be produced by mixing the present solvent 1, the present solvent 2, a surfactant and diflufenica.n, furthermore bromoxynil=octanoate and ioxynil=octanoate, if necessary, 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.
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.
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.
EXAMPLES
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
examples.
Preparation Example 1 Diflufenican(purity 91 %, 3.6 g as active ingredient), bromoxynil=octanoate(purity95.4%, 17.33gasactiveingredjent) and iOXynhl=octanoate(purity 96 %, 9.65 g as active ingredient) were added to propylene glycol diacetate(40.54 g) under heating and were dissolved. Then Rhodacal6o/BE(surfactant produced by Rhodia Nicca; 3.83 g) and Alkarnuls 0R40(surfactant produced by RhodiaNicca; 3.83 g) and were added to it. Furthermore, Solvesso 150 ND(aromatic hydrocarbon, mainly dO to Cli alkylbenzene, 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(referred as the emulsifiable concentrate of the present invention 1, hereinafter).
Test Example 1
Into a 100 ml - graduated cylinder with stopper, 99 ml of CIPAC standard water D (342ppm) was charged. Then 1 ml of the emulsifiable concentrate of the present invention 1 was added into the graduated cylinder and mixed. The graduated cylinder was left at 30 C for 2 hours. Then the stability of the emulsion was observed. The aqueous composition which was obtained by diluted the emulsifiable concentrate of the present invention 3. with water kept stable emulsion.
INDUSTRIAL APPLICABILITy
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.
Claims (11)
1. An emulsifiable concentrate comprising: 2',4t-difluoro-2(a,a,atrif1uoromto1y1oxy)njcotinani lide; a compound of formula (1): R1OoR2 wherein R' and R2 independently represent alkyl groups, A represents ethylene group, Irimethylene group, propylene group or tetramethylene group, and the sum of the number of carbon atoms contained by the groups R', R2 and A is from 4 to 10; an aromatic hydrocarbon; and a surfactant.
2. An emulsifiable concentrate according to claim 1, comprising: 2',41-difluoro-2-(a,a,a-trjfluoromtolyjoxy)nicotinanjljde; 4-cyano-2,6-dibromophenyl octanoate; 4-cyano-2,6-diiodophenyl octanoate; a compound of formula (1): R1OOR2 (1) wherein R' and R2 independently represent alkyl groups, A represents ethylene group, trimethylene group, propylene group or tetramethylene group, and the sum of the number of carbon atoms contained by the groups R', R2 and A is from 4 to 10; an aromatic hydrocarbon; and a surfactant.
3. An emulsifiable concentrate according to claim 1 or 2, comprising: 1 to 5% by weight of 2',4'-di fluoro-2-(a,a,a-tri fluoro-m-tolyloxy) nicotjnanjljde; 1 to 30% by weight of 4-cyano-2,6dibromopheny1 octanoate; 1 to 30% by weight of 4-cyano-2,6-djiodophenyl octanoate; to 80% by weight of a compound of formula (1): R1OOR2 wherein R' and R2 independently represent alkyl groups, A represents ethylene group, trimethylene group, propylene group or tetramethylene group, and the sum of the number of carbon atoms contained by the groups R', R2 and A is from 4 to 10; an aromatic hydrocarbon; and 4 to 20% by weight of a surfactant; wherein the total content of 4-cyano-2,6-dibromophenyl octanoate, 4-cyano- 2,6diiodophenyl octanoate and the aromatic hydrocarbon in the emulsifiable concentrate is from 15 to 80% by weight.
4. An emulsifiable concentrate according to claim 3, essentially consisting of: 1 to 5% by weight of 2',4t-difluoro2(a,a,atrifluoromto1yloxy) thcotjnanj1jd; 1 to 30% by weight of 4-cyano-2,6-dibrornophenyl octanoate; 1 to 30% by weight of 4-cyano-2,6-diiodophenyl octanoate; to 80% by weight of a compound of formula (1): 0 0 A (1) R''O O'R2 wherein R' and R2 independently represent alkyl groups, A represents ethylene group, trimethylene group, propylene group or tetramethylene group, and the sum of the number of carbon atoms contained in the groups R1, R2 and A is from 4 to 10; an aromatic hydrocarbon; and 4 to 20% by weight of a surfactant; wherein the total content of 4-cyano-2,6dibromophenyl octanoate, 4-cyano- 2,6- diiodophenyl octanoate and the aromatic hydrocarbon in the emulsifiable concentrate is from 15 to 80% by weight.
5. An emulsifiable concentrate according to any one of claims 1 to 4, wherein the weight ratio of the amount of the compound of formula (1) to the amount of is from 5:1 to 80:1.
6. An emulsifiable concentrate according to any one of claims 1 to 5, wherein the surfactant is a mixture of 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.
7. An emulsifiable concentrate according to any one of claims 1 to 5, wherein the surfactant is a mixture of dodecyl benzene sulfonic acid salt and polyoxyethylene castor oil; and the ratio by weight of the dodecyl benzene sulfonic acid salt to the polyoxyethylene castor oil is from 1:0. 1 to 1:10.
8. An emulsifiable concentrate according to any one of claims 1 to 7, wherein the compound of formula (1) is selected from ethylene glycol diacetate, ethylene glycol dipropionate, ethylene glycol dibutyrate, propylene glycol diacetate, propylene glycol dipropionate and 1,3propanediol diacetate.
9. An aqueous composition which is obtainable by diluting an emulsifiable concentrate according to any one of claims 1 to 8 with water.
10. An emulsifiable concentrate according to claim 1 substantially as hereinbefore described in Preparation Example 1.
11. An aqueous composition according to claim 9 substantially as hereinbefore described in Test Example 1.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2005101695A JP2006282528A (en) | 2005-03-31 | 2005-03-31 | Agrochemical composition |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB0606182D0 GB0606182D0 (en) | 2006-05-10 |
| GB2424583A true GB2424583A (en) | 2006-10-04 |
| GB2424583B GB2424583B (en) | 2007-04-04 |
Family
ID=36424717
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB0606182A Expired - Fee Related GB2424583B (en) | 2005-03-31 | 2006-03-28 | Emulsifiable concentrate |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JP2006282528A (en) |
| AU (1) | AU2006200730B2 (en) |
| BE (1) | BE1017083A3 (en) |
| DE (1) | DE102006013998B4 (en) |
| FR (1) | FR2883702B1 (en) |
| GB (1) | GB2424583B (en) |
| LU (1) | LU91231B1 (en) |
| NL (1) | NL1031387C2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104365603A (en) * | 2014-09-25 | 2015-02-25 | 南京华洲药业有限公司 | Mixed herbicide containing diflufenican and bromoxynil octanoate, and preparation method thereof |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5066881B2 (en) * | 2006-09-27 | 2012-11-07 | 住友化学株式会社 | Emulsion composition |
| JP5092428B2 (en) * | 2007-01-31 | 2012-12-05 | 住友化学株式会社 | Pesticide solution containing hydrophobic agrochemical active compound |
| CN107912428B (en) * | 2017-11-24 | 2021-01-05 | 山东农业大学 | Pesticide synergistic additive and preparation method thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5834400A (en) * | 1997-04-29 | 1998-11-10 | Isp Investments Inc. | Emulsifiable concentrate for a low dosage fluorinated agricultural chemical |
| WO2006029736A1 (en) * | 2004-09-18 | 2006-03-23 | Bayer Cropscience Gmbh | Liquid plant protection formulation comprising diflufenican |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK170870B1 (en) * | 1985-07-23 | 1996-02-26 | May & Baker Ltd | A method of controlling weeds using bromoxynil or ioxynil and diflufenican as well as product and herbicide preparation comprising bromoxynil or ioxynil and diflufenican |
| GB8630698D0 (en) * | 1986-12-23 | 1987-02-04 | May & Baker Ltd | Compositions of matter |
| GB8630806D0 (en) * | 1986-12-23 | 1987-02-04 | May & Baker Ltd | Compositions of matter |
| DE10343390A1 (en) * | 2003-09-19 | 2005-04-14 | Bayer Cropscience Gmbh | Surfactant / solvent mixtures |
-
2005
- 2005-03-31 JP JP2005101695A patent/JP2006282528A/en active Pending
-
2006
- 2006-02-22 AU AU2006200730A patent/AU2006200730B2/en not_active Ceased
- 2006-03-16 NL NL1031387A patent/NL1031387C2/en not_active IP Right Cessation
- 2006-03-27 DE DE102006013998.4A patent/DE102006013998B4/en not_active Expired - Fee Related
- 2006-03-27 FR FR0651050A patent/FR2883702B1/en not_active Expired - Fee Related
- 2006-03-28 GB GB0606182A patent/GB2424583B/en not_active Expired - Fee Related
- 2006-03-28 LU LU91231A patent/LU91231B1/en active
- 2006-03-28 BE BE2006/0196A patent/BE1017083A3/en active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5834400A (en) * | 1997-04-29 | 1998-11-10 | Isp Investments Inc. | Emulsifiable concentrate for a low dosage fluorinated agricultural chemical |
| WO2006029736A1 (en) * | 2004-09-18 | 2006-03-23 | Bayer Cropscience Gmbh | Liquid plant protection formulation comprising diflufenican |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104365603A (en) * | 2014-09-25 | 2015-02-25 | 南京华洲药业有限公司 | Mixed herbicide containing diflufenican and bromoxynil octanoate, and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| DE102006013998B4 (en) | 2017-02-16 |
| NL1031387C2 (en) | 2006-10-03 |
| DE102006013998A1 (en) | 2006-10-05 |
| AU2006200730A1 (en) | 2006-10-19 |
| FR2883702B1 (en) | 2009-12-18 |
| AU2006200730B2 (en) | 2011-05-12 |
| JP2006282528A (en) | 2006-10-19 |
| FR2883702A1 (en) | 2006-10-06 |
| LU91231B1 (en) | 2006-10-02 |
| BE1017083A3 (en) | 2008-02-05 |
| GB2424583B (en) | 2007-04-04 |
| GB0606182D0 (en) | 2006-05-10 |
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