IE86912B1 - Liquid agrochemical - Google Patents
Liquid agrochemical Download PDFInfo
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- IE86912B1 IE86912B1 IE2017/0047A IE20170047A IE86912B1 IE 86912 B1 IE86912 B1 IE 86912B1 IE 2017/0047 A IE2017/0047 A IE 2017/0047A IE 20170047 A IE20170047 A IE 20170047A IE 86912 B1 IE86912 B1 IE 86912B1
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- benzyl alcohol
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- 239000003905 agrochemical Substances 0.000 title claims abstract description 68
- 239000007788 liquid Substances 0.000 title claims abstract description 44
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims abstract description 153
- -1 pyridazine compound Chemical class 0.000 claims abstract description 106
- 235000019445 benzyl alcohol Nutrition 0.000 claims abstract description 51
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 45
- 239000004094 surface-active agent Substances 0.000 claims abstract description 11
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims abstract description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
- 125000001246 bromo group Chemical group Br* 0.000 claims abstract description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims description 21
- 150000005215 alkyl ethers Chemical class 0.000 claims description 19
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 claims description 8
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 claims description 8
- KWKXNDCHNDYVRT-UHFFFAOYSA-N Dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 claims description 7
- 239000002736 nonionic surfactant Substances 0.000 claims description 6
- 239000003945 anionic surfactant Substances 0.000 claims description 5
- 239000004495 emulsifiable concentrate Substances 0.000 claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 238000002360 preparation method Methods 0.000 description 37
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 24
- 239000000126 substance Substances 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 18
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 11
- HCWYXKWQOMTBKY-UHFFFAOYSA-N calcium;dodecyl benzenesulfonate Chemical compound [Ca].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 HCWYXKWQOMTBKY-UHFFFAOYSA-N 0.000 description 11
- 239000012456 homogeneous solution Substances 0.000 description 10
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 10
- 239000011780 sodium chloride Substances 0.000 description 10
- PBMFSQRYOILNGV-UHFFFAOYSA-N Pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 9
- 229920000090 poly(aryl ether) Polymers 0.000 description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 239000010452 phosphate Substances 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- 229920001214 Polysorbate 60 Polymers 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 3
- 239000004359 castor oil Substances 0.000 description 3
- 235000019438 castor oil Nutrition 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HNXNKTMIVROLTK-UHFFFAOYSA-N N,N-dimethyldecanamide Chemical compound CCCCCCCCCC(=O)N(C)C HNXNKTMIVROLTK-UHFFFAOYSA-N 0.000 description 2
- 229950006451 Sorbitan laurate Drugs 0.000 description 2
- NWGKJDSIEKMTRX-MDZDMXLPSA-N Sorbitan oleate Chemical compound CCCCCCCC\C=C\CCCCCCCC(=O)OCC(O)C1OCC(O)C1O NWGKJDSIEKMTRX-MDZDMXLPSA-N 0.000 description 2
- 229950004959 Sorbitan oleate Drugs 0.000 description 2
- 229950011392 Sorbitan stearate Drugs 0.000 description 2
- 229960000391 Sorbitan trioleate Drugs 0.000 description 2
- 239000004147 Sorbitan trioleate Substances 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N Trimethylglycine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- LWZFANDGMFTDAV-WYDSMHRWSA-N [2-[(2R,3R,4S)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCC(O)[C@H]1OC[C@H](O)[C@H]1O LWZFANDGMFTDAV-WYDSMHRWSA-N 0.000 description 2
- HVUMOYIDDBPOLL-IIZJTUPISA-N [2-[(2R,3S,4R)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)[C@H]1OC[C@@H](O)[C@@H]1O HVUMOYIDDBPOLL-IIZJTUPISA-N 0.000 description 2
- PRXRUNOAOLTIEF-XDTJCZEISA-N [2-[(2R,3S,4R)-4-hydroxy-3-[(Z)-octadec-9-enoyl]oxyoxolan-2-yl]-2-[(Z)-octadec-9-enoyl]oxyethyl] (Z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@@H](O)[C@@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-XDTJCZEISA-N 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000002280 amphoteric surfactant Substances 0.000 description 2
- 239000003093 cationic surfactant Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 235000011067 sorbitan monolaureate Nutrition 0.000 description 2
- 235000019337 sorbitan trioleate Nutrition 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- WJYAJBDKANFOID-AWEZNQCLSA-N (2S)-2-(dodecylamino)propanoic acid Chemical compound CCCCCCCCCCCCN[C@@H](C)C(O)=O WJYAJBDKANFOID-AWEZNQCLSA-N 0.000 description 1
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-Trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-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
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 description 1
- YQZBFMJOASEONC-UHFFFAOYSA-N 1-Methyl-2-propylbenzene Chemical compound CCCC1=CC=CC=C1C YQZBFMJOASEONC-UHFFFAOYSA-N 0.000 description 1
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-Methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 1
- UVMGANPLBFFQIO-UHFFFAOYSA-N 1-dodecylnaphthalene Chemical compound C1=CC=C2C(CCCCCCCCCCCC)=CC=CC2=C1 UVMGANPLBFFQIO-UHFFFAOYSA-N 0.000 description 1
- WDRZVZVXHZNSFG-UHFFFAOYSA-N 1-ethenylpyridin-1-ium Chemical class C=C[N+]1=CC=CC=C1 WDRZVZVXHZNSFG-UHFFFAOYSA-N 0.000 description 1
- HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical compound CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 description 1
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 description 1
- WPPOGHDFAVQKLN-UHFFFAOYSA-N 1-octylpyrrolidin-2-one Chemical compound CCCCCCCCN1CCCC1=O WPPOGHDFAVQKLN-UHFFFAOYSA-N 0.000 description 1
- ZADDSDYVJJAKCI-UHFFFAOYSA-N 1-tridecylnaphthalene Chemical compound C1=CC=C2C(CCCCCCCCCCCCC)=CC=CC2=C1 ZADDSDYVJJAKCI-UHFFFAOYSA-N 0.000 description 1
- OGYMWUMPVDTUCW-UHFFFAOYSA-L 2,2-bis(2-ethylhexyl)-3-sulfobutanedioate Chemical compound CCCCC(CC)CC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CC(CC)CCCC OGYMWUMPVDTUCW-UHFFFAOYSA-L 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-L 2-sulfobutanedioate Chemical class OS(=O)(=O)C(C([O-])=O)CC([O-])=O ULUAUXLGCMPNKK-UHFFFAOYSA-L 0.000 description 1
- CSWYKLRZFCSAHI-UHFFFAOYSA-O 3-pyrimidin-1-ium-1-ylpropanoic acid Chemical compound OC(=O)CC[N+]1=CC=CN=C1 CSWYKLRZFCSAHI-UHFFFAOYSA-O 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
- 229960001950 Benzethonium Chloride Drugs 0.000 description 1
- UREZNYTWGJKWBI-UHFFFAOYSA-M Benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 description 1
- GUVUOGQBMYCBQP-UHFFFAOYSA-N DMPU Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 1
- 229940067606 Lecithin Drugs 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L Sulphite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- NHYCGSASNAIGLD-UHFFFAOYSA-N chlorine monoxide Inorganic materials Cl[O] NHYCGSASNAIGLD-UHFFFAOYSA-N 0.000 description 1
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
- TWFQJFPTTMIETC-UHFFFAOYSA-N dodecan-1-amine;hydron;chloride Chemical compound [Cl-].CCCCCCCCCCCC[NH3+] TWFQJFPTTMIETC-UHFFFAOYSA-N 0.000 description 1
- VICYBMUVWHJEFT-UHFFFAOYSA-N dodecyltrimethylammonium ion Chemical class CCCCCCCCCCCC[N+](C)(C)C VICYBMUVWHJEFT-UHFFFAOYSA-N 0.000 description 1
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000008172 hydrogenated vegetable oil Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- LPEKGGXMPWTOCB-VKHMYHEASA-N methyl (S)-lactate Chemical compound COC(=O)[C@H](C)O LPEKGGXMPWTOCB-VKHMYHEASA-N 0.000 description 1
- WSVDSBZMYJJMSB-UHFFFAOYSA-N octadecylbenzene Chemical compound CCCCCCCCCCCCCCCCCCC1=CC=CC=C1 WSVDSBZMYJJMSB-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Abstract
The present invention provides a liquid agrochemical comprising a pyridazine compound of the formula (1): wherein Rl is chloro atom, bromo atom, cyano group or methyl group; and R2 is hydrogen atom or fluoro atom, a surfactant(s), and benzyl alcohol and an aromatic hydrocarbon(s) at a given content and content ratio thereof, which has excellent properties.
Description
DESCRIPTION LIQUID AGROCHEMICAL TECHNICAL FIELD
[0001] This application. claims priority’ to and. benefit of Japanese Patent Application Serial No. 2016-041875 filed on March 4, 2016, the entire contents of which are incorporated by reference.
The present invention relates to a liquid agrochemical.
BACKGROUND ART
[0002] Heretofore, it has been known (see Patent Documents 1 and 2) as an active compound for controlling plant diseases, a pyridazine compound of the formula (I): wherein R1 is chloro atom, bromo atom, cyano group or methyl group; and R2 is hydrogen atom or fluoro atom.
CITATION LIST PATENT DOCUMENT
[0003] Patent Document 1: W0 2005/121104 Patent Document 2: WO 2006/001175 SUMMARY OF THE INVENTION (PROBLEMS TO BE SOLVED BY INVENTION)
[0004] The object of the present invention is to provide a liquid agrochemical comprising the above-mentioned pyridazine compound and having excellent properties.
(MEANS TO SOLVE PROBLEMS)
[0005] The inventors have performed intensive studies to find a liquid agrochemical comprising the [above-mentioned pyridazine compound and having excellent properties, and as a result, found that a liquid agrochemical comprising the above-mentioned pyridazine compound, a surfactant(s), benzyl alcohol and an aromatic hydrocarbon(s) has excellent properties.
That is, the present invention provides the following aspects [1] to [8]. [1] A liquid agrochemical comprising 1 to 11% by weight of a pyridazine compound of formula (I): wherein R1 is chloro atom, bromo atom, cyano group or methyl group; and R2 is hydrogen atom or fluoro atom, 1 to 30% by weight of a surfactant(s), benzyl alcohol and an aromatic hydrocarbon(s), wherein the total content of benzyl alcohol and the aromatic hydrocarbon(s) is within the range of 50 to 98% by weight and the weight ratio of benzyl alcohol to the aromatic hydrocarbon(s) (benzyl alcohol: aromatic hydrocarbon(s)) is within the range of 30:70 to 85:15. [2] The liquid agrochemical as described in [1] wherein the weight ratio of benzyl alcohol to the aromatic hydrocarbon(s) (benzyl alcohol: aromatic hydrocarbon(s)) is within the range of 30:70 to 80:20. [3] The liquid agrochemical as described in [1] or [2] wherein the aromatic hydrocarbon(s) is at least one alkylbenzene or at least one alkylnaphthalene. [4] The liquid agrochemical as described in any one of [1] to [3] wherein the content of pyridazine compound is within the range of 4 to 10% by weight. [5] The liquid agrochemical as described in any one of [1] to [3] wherein the content of pyridazine compound is within the range of 4 to 8% by weight. [6] The liquid agrochemical as described in any one of [1] to [5] wherein the surfactant comprises a combination of a nonionic surfactant(s) and an anionic surfactant(s). [7] The liquid agrochemical as described in any one of [1] to [5] wherein the surfactant(s) comprises dodecylbenzene sulfonate in combination with polyoxyalkylene polyaryl ether or polyoxyalkylene alkyl ether. [8] The liquid agrochemical as described in any one of [1] to [7] which is an emulsifiable concentrate.
[0006] The present invention can provide a liquid agrochemical comprising the above—mentioned pyridazine compound and also having excellent properties in terms of emulsion stability and storage stability at low temperature.
MODE FOR CARRYING OUT THE INVENTION [ooo7] The liquid agrochemical of the present invention (herein after referred to as the "present agrochemicalfl comprises a pyridazine compound of formula (I): wherein R1 is chloro atom, bromo atom, cyano group or methyl group; and R2 is hydrogen atom or fluoro atom (hereinafter referred to as the "present pyridazine compound").
[0008] The present pyridazine compound of formula (I) wherein R1 is chloro atom or bromo atom may be prepared according to a disclosed in WO method known in the art, as 2005/121104, which hereby is incorporated by reference.
The present pyridazine compound of formula (I) wherein R1 is methyl group may be prepared according to a method known j11 the arts as disclosed iJ1 WO 2006/001175, which hereby is incorporated by reference.
The present pyridazine compound of formula (I) wherein R1 is cyano group may be prepared according to a method known in the art, as disclosed in WO 2014/013841, which hereby is incorporated by reference.
[0009] Examples of the present pyridazine compound include: The compound of formula (I) wherein R1 is chloro atom and R2 is hydrogen atom; The compound of formula (I) wherein R1 is bromo atom and R2 is hydrogen atom; The compound of formula (I) wherein R1 is cyano group and R2 is hydrogen atom; The compound of formula (I) wherein R1 is methyl group and R2 is hydrogen atom; The compound of formula (I) wherein R1 is chloro atom and R2 is fluoro atom; The compound of formula (I) wherein R1 is bromo atom and R2 is fluoro atom; The compound of formula (I) wherein R2 is cyano group and R2 is fluoro atom; and The compound of formula (I) wherein R1 is methyl group and R2 is fluoro atom.
[0010] The present agrochemical comprises 1 to 11% by weight, preferably 4 to 10% by weight, or more preferably 4 to 8% by weight of the present pyridazine compound.
[0011] The present agrochemical comprises benzyl alcohol.
Any commercially available benzyl alcohol may be used.
[0012] The present agrochemical comprises an aromatic hydrocarbon(s). Examples emf the aromatic hydrocarbon(s) include alkylbenzenes such as monoalkylbenzenes, dialkylbenzenes and trialkylbenzenes; alkylnaphthalenes such as monoalkylnaphthalene, dialkylnaphthalene, trialkylnaphthalene; phenylxylylethane; and 1-phenyl-1- ethylphenylethane; and mixtures thereof.
Examples of alkylbenzene include toluene, xylene, trimethylbenzene, ethylbenzene, methylethylbenzene, methylpropylbenzene, dimethylethylbenzene, and octadecylbenzene. Specific examples of alkylnaphthalene include methylnaphthalene, dimethylnaphthalene, dodecylnaphthalene, and tridecylnaphthalene.
[0013] In the present agrochemical, any commercially available aromatic hydrocarbon solvent may be used as the aromatic hydrocarbon(s). Examples of such commercially available aromatic hydrocarbon solvent include Nisseki Hisol SAS-296 (a mixture of 1-phenyl-l—xylylethane and 1- phenyl-1—ethylphenylethane, manufactured by JX Nippon Oil & Energy Corporation), Solvesso 100 (mainly composed of, as aromatic hydrocarbons, C9-C10 dialkyl and trialkylbenzene, Chemical manufactured by ExxonMobil Company, Inc.), Solvesso 150 (mainly composed of, as aromatic hydrocarbons, C10—C11 alkylbenzene, manufactured by ExxonMobil Chemical Company, Solvesso 15OND Inc.), (mainly composed of, as aromatic hydrocarbons, C10—C11 alkylbenzene, manufactured by ExxonMobil Chemical Company, Inc.), Solvesso 200 (mainly composed of, as aromatic hydrocarbons, C10-C13 alkylnaphthalene, manufactured by ExxonMobil Chemical Company, Inc.) and Solvesso 200ND (mainly composed of, as aromatic hydrocarbons, ClO~Cl3 alkylnaphthalene, manufactured by ExxonMobil Chemical Company, Inc.), Ipsol 100 (mainly composed of C9 aromatic hydrocarbons, manufactured by Idemitsu Kosan Co., Ltd.), Ipsol 150 (mainly composed of C10 aromatic hydrocarbons, manufactured by Idemitsu Kosan Co., Ltd.), T—SOL 150 FLUID (manufactured by TonenGeneral SELLSOL A 100 Sekiyu K.K.), (mainly composed of C9-C10 aromatic hydrocarbons, manufactured by Shell Chemicals), SELLSOL A150 (mainly composed of C9-C11 aromatic hydrocarbons, manufactured by Shell Chemicals) and the others.
[0014] The weight ratio of benzyl alcohol and the aromatic hydrocarbon(s) (benzyl alcohol: aromatic hydrocarbon(s)) in the present agrochemical is within the range of 30:70 to 85:15, preferably 30:70 to 80:20, and more preferably 30:70 to 70:30.
[0015] The total content of benzyl alcohol and the aromatic hydrocarbon(s) in the present agrochemical is 50 to 98% by weight, and preferably 70 to 98% by weight, and more preferably 70 to 95% by weight.
[0016] The present agrochemical comprises a surfactant(s).
Examples of the surfactant include nonionic surfactants, anionic surfactants, cationic surfactants and amphoteric surfactants.
[0017] Examples of the nonionic surfactant include polyoxyethylene-polyoxypropylene block copolymers; polyoxyalkylene fatty acid esters such as polyoxyethylene fatty acid esters and polyoxyethylene polyoxypropylene fatty acid esters; polyoxyalkylene polyaryl ethers such as polyoxyethylene tristyrylphenyl ethers, polyoxyethylene polyaryl ethers, and polyoxyethylene polyoxypropylene polyaryl ethers; polyoxyalkylene alkylaryl ethers such as polyoxyethylene alkylaryl ethers, and polyoxyethylene polyoxypropylene alkylaryl ethers; polyoxyalkylene alkyl ethers such as polyoxyethylene alkyl ethers, and polyoxyethylene polyoxypropylene alkyl ethers; polyoxyalkylene vegetable oils such as polyoxyethylene castor oil and polyoxyethylene polyoxypropylene castor oil; polyoxyalkylene hydrogenated vegetable oils such as polyoxyethylene hydrogenated castor oil; glycerin fatty acid esters; sorbitan fatty acid esters such as sorbitan laurate, sorbitan stearate, sorbitan oleate, and sorbitan trioleate; and polyoxyalkylene sorbitan fatty acid esters such as polyoxyethylene sorbitan laurate, polyoxyethylene sorbitan stearate, polyoxyethylene sorbitan oleate, and polyoxyethylene sorbitan trioleate. Among the above- mentioned nonionic surfactants, one or more nonionic surfactant selected from the group consisting of polyoxyalkylene polyaryl ethers and polyoxyalkylene alkyl ethers is preferably used.
[0018] Examples of the anionic surfactant include alkylarylsulfonates such. as dodecylbenzene sulfonate; dialkyl sulfosuccinates such as di-(2- ethylhexyl)sulfosuccinate; polyoxyalkylene polyaryl ether sulfate ester salts such as polyoxyethylene distyrylphenyl ether sulfate ester salts; polyoxyalkylene polyaryl ether phosphate ester salts such as polyoxyethylene tristyryl phenyl ether phosphate ester salts; polyoxyalkylene alkylaryl ether phosphate ester salts such as polyoxyethylene alkylaryl ether phosphate ester salts; polyoxyalkylene alkyl ether phosphate ester salts such as polyoxyethylene alkyl ether phosphate ester salts.
Examples of such sulfonate, sulfate ester salts and phosphate ester salts include sodium salt, potassium salt, calcium salt and ammonium salt. Among the above—mentioned anionic surfactants, dodecylbenzene sulfonate is preferably used. ’active ingredient(s)
[0019] Examples of the cationic surfactant include alkylamine hydrochlorides such as dodecylamine hydrochloride; alkyl quaternary ammonium salts such as dodecyltrimethyl ammonium salt, alkyldimethylbenzyl ammonium salt, alkylpyridinium salt, alkylisoquinolinium salt, and dialkylmorpholinium salt; benzethonium chloride; and polyalkyl vinyl pyridinium salt.
[0020] Examples of the amphoteric surfactant include N- laurylalanine, N,N,N~trimethylaminopropionic acid, N,N,N- trihydroxyethylaminopropionic acid, N—hexyl—N,N- dimethylamino acetic acid, 1-(2—carboxyethyl) pyrimidinium betaine, and lecithin.
[0021] In the present agrochemical, one or more of these surfactants are used, and the total content thereof is within the range of 1 to 30% by weight, preferably 1 to 20% by weight, more preferably 1 to 15% by weight, and still more preferably 1 to 10% by weight.
[0022] The present agrochemical may further comprise another for controlling plant diseases, in combination with the present pyridazine compound.
[0023] The present agrochemical may further comprise an auxiliary agent(s) for formulation, such as a defoaming agent. When the present agrochemical comprises the auxiliary agent(s) for formulation, the total content of such auxiliary agent(s) is within the range of 0.0001 to 30% by weight.
[0024] A method of applying the present agrochemical is not limited to specific ones. Although the present agrochemical as itself can be applied as a plant disease control agent, it also can be applied as an emulsifiable concentrate method in according to a commonly used agrochemical art, for example, applying it as a liquid diluted with water for controlling plant diseases.
The present agrochemical exists in the liquid state at 25°C.
EXAMPLES
[0025] The present invention is described in more detail below by way of Examples including Preparation Examples and Test Examples and the like, but the present invention is not limited only to these Examples.
In the above—mentioned following Examples, the pyridazine compound of formula (I) wherein. R1 is chloro atom and R2 is hydrogen atom is referred to as the "present pyridazine compound (l)".
[0026] First, Preparation Examples for the present agrochemical are described.
[0027] Preparation Examples 1 to 4 The present pyridazine compound (1), Phenylsulfonat Cal (calciunl dodecylbenzenesulfonate, manufactured by Clariant), Emulsogen TS 290 (polyoxyethylene tristyrylphenyl ether, manufactured by Clariant), benzyl alcohol and Solvesso 200ND (mainly composed of, as aromatic hydrocarbons, C10-C13 alkylnaphthalene, manufactured by ExxonMobil Chemical Company, were mixed at each Inc.) weight ratio shown in Table 1, and the mixture was stirred until a homogeneous solution was formed to obtain each of the present agrochemicals.
[0028] Table 1 Preparation Example No. 1 2 3 4 Present pyridazine 10 10 10 10 compound (1) Phenylsulfonat Cal 00 (.0 Lu) 0») Emulsogen T8290 7 7 7 7 Benzyl alcohol 24 40 56 64 Solvesso 20OND 56 40 24 16 Benzyl alcohol: Solvesso 30:70 50:50 70:30 80:20 20OND (weight ratio)
[0029] Preparation Examples 5 to 8 The present pyridazine compound (1), Agnique AMD 810 (a mixture of N,N-dimethyloctane amide and N,N- dimethyldecanamide, manufactured Inf BASF), Phenylsulfonat Cal (calcium dodecylbenzenesulfonate, manufactured by Clariant), Emulsogen TS 290 (polyoxyethylene tristyrylphenyl ether, manufactured by Clariant), benzyl alcohol and Solvesso 200ND (mainly composed of, as aromatic hydrocarbons, C10~C13 alkylnaphthalene, manufactured by ExxonMobil Chemical Company, Inc.) were mixed at each weight ratio shown in Table 2, and the mixture was stirred until a homogeneous solution was formed to obtain each of the present agrochemicals.
[0030] Table 2 Preparation Example No. 5 6 7 8 Present pyridazine 8 8 8 8 compound (1) Agnique AMD8lO 10 10 10 10 Phenylsulfonat Cal 3 3 3 3 Emulsogen TS290 7 7 7 7 Benzyl alcohol 21.6 36 50.4 57.6 Solvesso 200ND 50.4 36 21.6 14.4 Benzyl alcohol: Solvesso 30:70 50:50 70:30 80:20 ZOOND (weight ratio)
[0031] Preparation Examples 9 to 12 The present pyridazine compound (1), Rhodasurf 860/P (polyoxyethylene alkyl ether, manufactured by Solvay Nicca, Ltd.), Phenylsulfonat Cal (calcium dodecylbenzenesulfonate, manufactured by Clariant), Emulsogen TS 290 (polyoxyethylene tristyrylphenyl ether, manufactured by Clariant), benzyl alcohol and Solvesso ZOOND (mainly composed of, as aromatic hydrocarbons, C10-C13 alkylnaphthalene, manufactured by‘ ExxonMobil Chemical Company, Inc.) were mixed at each weight ratio shown in Table 3, and the mixture was stirred until a homogeneous solution was formed to obtain each of the present agrochemicals.
[0032] Table 3 Preparation Example No. 9 10 11 12 Present pyridazine 8 8 8 8 compound (1) Rhodasurf 860/P 10 10 10 10 Phenylsulfonat Cal 3 3 3 3 Emulsogen TS290 7 7 7 7 Benzyl alcohol 21.6 36 50.4 57.6 Solvesso 200ND 50.4 36 21.6 14.4 Benzyl alcohol: Solvesso 30:70 50:50 70:30 80:20 2OOND (weight ratio)
[0033] Preparation Examples 13 to 16 The present pyridazine compound (1), Phenylsulfonat Cal (calcium dodecylbenzenesulfonate, manufactured by Clariant), Emulsogen TS 290 (polyoxyethylene tristyrylphenyl ether, manufactured by Clariant), benzyl alcohol and Solvesso 150ND (mainly composed of, as aromatic hydrocarbons, ClO—C11 alkylbenzene, manufactured by ExxonMobil Chemical Company, were mixed at each Inc.) weight ratio shown in Table 4, and the mixture was stirred until a homogeneous solution was formed to obtain each of the present agrochemicals.
[0034] Table 4 Preparation Example No. l3 14 15 16 Present pyridazine 8 8 8 8 compound (1) Phenylsulfonat Cal 3 3 3 3 Emulsogen TS29O 7 7 7 7 Benzyl alcohol 24.6 41 57.4 65.4 Solvesso 15OND 57.4 41 24.6 16.4 Benzyl alcohol: Solvesso 30:70 50:50 70:30 80:20 150ND (weight ratio)
[0035] Preparation Examples 17 to 20 The present pyridazine compound (1), Phenylsulfonat Cal (calciunl dodecylbenzenesulfonate, manufactured by Clariant), Emulsogen TS 290 (polyoxyethylene tristyrylphenyl ether, manufactured by Clariant), and benzyl alcohol and xylene were mixed at each weight ratio shown in Table 5, and the mixture was stirred until a homogeneous solution was formed to obtain each of the present agrochemicals.
[0036] Table 5 Preparation Example No. 17 18 19 20 Present pyridazine 8 8 8 8 compound (1) Phenylsulfonat Cal 3 3 3 3 Emulsogen TS290 7 7 7 7 Benzyl alcohol 24.6 41 57.4 65.6 Xylene 57.4 41 24.6 16.4 Benzyl alcohol: Xylene 30:70 50:50 70:30 80:20 (weight ratio)
[0037] Preparation Example 21 Eight (8) parts by weight of the present pyridazine compound (1), 3 parts by weight of Phenylsulfonat Cal (calcium dodecylbenzenesulfonate, manufactured by Clariant), 7 parts by weight of Emulsogen TS290 (polyoxyethylene tristyrylphenyl ether, manufactured by Clariant), 69.7 parts by weight of benzyl alcohol and 12.3 parts by weight of Solvesso 200ND (mainly composed of, as aromatic hydrocarbons, C10—C13 alkylnaphthalene, manufactured by ExxonMobil Chemical Company, Inc.) were mixed to obtain the present agrochemical.
[0038] Preparation Example 22 Eight (8) parts by weight of the present pyridazine compound (1), 10 parts by weight of ATPLUS 245 (polyoxyethylene polyoxypropylene alkyl ether, manufactured by Croda), 3 parts by weight of Phenylsulfonat Cal (calcium dodecylbenzenesulfonate, manufactured by Clariant), 7 parts by weight of TS290 Emulsogen (polyoxyethylene tristyrylphenyl ether, manufactured by Clariant), 20 parts by weight of PURASOLV ML (methyl L-lactate, manufactured by Corbion purac), 27 parts by weight of benzyl alcohol and 25 parts by weight of Solvesso 200ND (mainly composed of, as aromatic hydrocarbons, C10-C13 alkylnaphthalene, manufactured by ExxonMobil Chemical Company, Inc.) were mixed to obtain the present agrochemical.
[0039] Preparation Example 23 Eight (8) parts by weight of the present pyridazine compound (1), 10 parts by weight of ATPLUS 245 (polyoxyethylene polyoxypropylene alkyl ether, manufactured by Croda), 3 parts by weight of Phenylsulfonat Cal (calcium dodecylbenzenesulfonate, manufactured by Clariant), 7 parts by weight of Emulsogen TS29O (polyoxyethylene tristyrylphenyl ether, manufactured by Clariant), 20 parts of Sulfadone LP 100 by weight (N—octyl-2—pyrrolidone, manufactured by .ASHLAND), 27 parts by weight of benzyl alcohol and 25 parts by weight of Solvesso 20OND (mainly composed of, as aromatic hydrocarbons, ClO—Cl3 alkylnaphthalene, manufactured by ExxonMobil Chemical Company, Inc.) were mixed to obtain the present agrochemical.
[0040] Preparation Example 24 Eight (8) parts by weight of the present pyridazine compound (1), 10 parts by weight of ATPLUS 245 (polyoxyethylene polyoxypropylene alkyl ether, manufactured by Croda), 3 parts by weight of Phenylsulfonat Cal (calcium dodecylbenzenesulfonate, manufactured by Clariant), 7 parts by weight of Emulsogen TS29O (polyoxyethylene tristyrylphenyl ether, manufactured by Clariant), 20 parts by weight of diethyl oxalate, 27 parts by weight of benzyl alcohol and 25 parts by weight of Solvesso 200ND (mainly composed of, as aromatic hydrocarbons, C10—Cl3 alkylnaphthalene, manufactured by ExxonMobi1 Chemical Company, Inc.) were mixed to obtain the present agrochemical.
[0041] Preparation Example 25 Ten (10) parts by weight of the present pyridazine compound (1), 10 parts by weight of ATPLUS 245 (polyoxyethylene polyoxypropylene alkyl ether, manufactured by Croda), 3 parts by weight of Phenylsulfonat Cal (calcium dodecylbenzenesulfonate, manufactured by Clariant), 7 parts by weight of Emulsogen T8290 (polyoxyethylene tristyrylphenyl ether, manufactured by Clariant), 10 parts by weight of N,N'-dimethylpropyleneurea, 30 parts by weight of benzyl alcohol and 30 parts by weight of Solvesso 2OOND (mainly composed of, as aromatic hydrocarbons, C10—Cl3 alkylnaphthalene, manufactured by ExxonMobil Chemical Company, Inc.) were mixed to obtain the present agrochemical.
[0042] Next, Reference Preparation Examples are described.
[0043] Reference Preparation Examples 1 to 3 The present pyridazine compound (1), Phenylsulfonat Cal (calciunl dodecylbenzenesulfonate, manufactured by Clariant), Emulsogen TS290 (polyoxyethylene tristyrylphenyl ether, manufactured by Clariant), benzyl alcohol and Solvesso 200ND (mainly composed of, as aromatic hydrocarbons, C10-C13 alkylnaphthalene, manufactured by ExxonMobi1 Chemical Company, were mixed at each Inc.) weight ratio shown in Table 6, and the mixture was stirred until a homogeneous solution was formed to obtain each of liquid agrochemicals.
[0044] Table 6 Reference Preparation 1 2 3 Example No.
Present pyridazine 10 10 10 compound (1) Phenylsulfonat Cal 3 3 3 Emulsogen T8290 7 7 7 Benzyl alcohol 0 16 80 Solvesso 200ND 80 64 0 Benzyl alcohol: Solvesso 0:100 20:80 100:0 20OND (weight ratio)
[0045] Reference Preparation Examples 4 to 6 The present pyridazine compound (1), Agnique AMD 810 (a mixture of N,N—dimethyloctane amide and N,N- dimethyldecanamide, manufactured knr BASF), Phenylsulfonat Cal (calcium: dodecylbenzenesulfonate, manufactured by Clariant), Emulsogen TS290 (polyoxyethylene tristyrylphenyl ether, manufactured by Clariant), benzyl alcohol and Solvesso 200ND (mainly composed of, as aromatic hydrocarbons, C10—Cl3 alkylnaphthalene, manufactured by ExxonMobil Chemical Company, Inc.) were mixed at each weight ratio shown in Table 7, and the mixture was stirred until a homogeneous solution was formed to obtain each of liquid agrochemicals.
[0046] Table 7 Reference Preparation 4 5 6 Example No.
Present pyridazine 8 P 8 8 compound (1) Agnique AMD 810 10 10 10 Phenylsulfonat Cal 3 3 3 Emulsogen TS29O 7 7 7 Benzyl alcohol 0 14.4 72 Solvesso 20OND 72 57.6 0 Benzyl alcohol: Solvesso 0:100 20:80 100:0 200ND (weight ratio)
[0047] Reference Preparation Examples 7 and 8 The present pyridazine compound (1), Rhodasurf 860/P (polyoxyethylene alkyl ether, manufactured by Solvay Nicca, Ltd.), Phenylsulfonat Cal (calcium dodecylbenzenesulfonate, manufactured by Clariant), Emulsogen TS290 (polyoxyethylene tristyrylphenyl ether, manufactured by Clariant), benzyl alcohol and Solvesso 200ND (mainly composed of, as aromatic hydrocarbons, Cl0—Cl3 alkylnaphthalene, manufactured by ExxonMobil Chemical Company, Inc.) were mixed at each weight ratio shown in Table 8, and the mixture was stirred until a homogeneous solution was formed to obtain each of liquid agrochemicals.
[0048] Table 8 Reference Preparation 7 8 Example No.
Present pyridazine 8 8 compound (1) Rhodasurf 860/P 10 10 Phenylsulfonat Cal 3 3 Emulsogen TS290 7 7 Benzyl alcohol 0 72 Solvesso 2OOND 72 O Benzyl alcohol: Solvesso 0:100 100:0 20OND (weight ratio)
[0049] Reference Preparation Examples 9 and 10 The present pyridazine compound (1), Phenylsulfonat Cal (calcium dodecylbenzenesulfonate, manufactured by Clariant), Emulsogen TS290 (polyoxyethylene tristyrylphenyl ether, manufactured by Clariant), benzyl alcohol and Solvesso l50ND (mainly composed of, as aromatic hydrocarbons, C10-C11 alkylbenzene, manufactured by ExxonMobil Chemical Company, Inc.) were mixed at each weight ratio shown in Table 9, and the mixture was stirred until a homogeneous solution was formed to obtain each of liquid agrochemicals.
[0050] Table 9 Reference Preparation 9 10 Example No.
Present pyridazine 8 8 compound (1) Phenylsulfonat Cal 3 3 Emulsogen TS 290 7 7 Benzyl alcohol 0 16.4 Solvesso 150ND 82 65.6 Benzyl alcohol: Solvesso 0:100 20:80 150ND (weight ratio)
[0051] Reference Preparation Example 11 Eight (8) parts by weight of the present pyridazine compound (1), 3 parts by weight of Phenylsulfonat Cal (calcium dodecylbenzenesulfonate, manufactured by Clariant), 7 parts by weight of Emulsogen TS290 (polyoxyethylene tristyrylphenyl ether, manufactured by Clariant), 82 parts by weight of xylene were mixed, and the mixture was stirred until a homogeneous solution was formed to obtain a liquid agrochemical.
[0052] Further, Test Example is described.
[0053] Test Example 1 Twenty (20) ml of each of the liquid agrochemicals obtained in the Preparation Examples 1 to 25 and the Reference Preparation Examples 1 to 11 was put into a glass tube, and kept at 0°C. Each of the liquid agrochemicals was kept for 7 days, followed by checking whether there is any crystal precipitation in each of the liquid agrochemicals.
Results showed that no crystal precipitation was found in the present agrochemicals obtained in Preparation Examples 1 to 25 and the liquid agrochemicals obtained in Reference Preparation Examples 3, 6 and 8. On the other hand, the crystal precipitation was found in the liquid agrochemicals obtained in Reference Preparation Examples 1, 2, 4, 5, 7, 9, 10 and 11.
[0054] Test Example 2 The following test was conducted using the present agrochemicals obtained in Preparation Examples 1 to 25 and the liquid agrochemicals obtained in Reference Preparation Examples 1 to 11.
Ninety nine (99) ml of CIPAC standard water D (hardness: 342 ppm) at 30°C was put in a 100 ml measuring cylinder with a stopper.
One (1) ml of the testing liquid agrochemical was dropped slowly from a height of approximately 8 cm above the surface of the water, and the measuring cylinder was then stoppered. The measuring cylinder was inverted by 180 degrees in 1 second and then returned into its original position in 1 second. After repeating this operation 10 times, the measuring cylinder was allowed to stand in a thermostat chamber at 30°C for 2 hours. Thereafter, state of the liquid in the neasuring cylinder was visually‘ observed to evaluate the emulsion stability.
Results showed that the liquid containing each of the present agrochemicals obtained in Preparation Examples 1 to 25 and the liquid agrochemicals obtained in Reference Preparation Examples 1, 2, 4, 5, 7, 9, 10 and 11 were kept in a homogeneous emulsified state. On the other hand, the crystal precipitation was found on the bottom face of the cylinder in the liquid containing each of the liquid agrochemicals obtained in Reference Preparation Examples 3, 6 and 8.
Claims (8)
1. A liquid agrochemical comprising 1 to 11% by weight of a pyridazine compound of formula (I): R2 PO 0 /| CH3 U) 5 F R1 \N’N wherein R1 is chloro atom, bromo atom, cyano group or methyl group; and R2 is hydrogen atom or fluoro atom, 10 1 to 30% by weight of a surfactant(s), benzyl alcohol and an aromatic hydrocarbon(s), wherein the total content of benzyl alcohol and the aromatic hydrocarbon(s) is within the range of 50 to 98% by weight 15 and the weight ratio of benzyl alcohol to the aromatic hydrocarbon(s) (benzyl alcohol: aromatic hydrocarbon(s)) is within the range of 30:70 to 85:15.
2. The liquid agrochemical according to claim 1 wherein 20 the weight ratio of benzyl alcohol to the aromatic f. hydrocarbon(s) (benzyl alcohol: aromatic hydrocarbon(s)) is ‘Jwithin the range of 30:70 to 80:20.
3. ; The liquid. agrochemical according' to tclaim 21 or‘ 2 27 wherein the aromatic hydrocarbon(s) is at least one alkylbenzene or at least one alkylnaphthalene.
4. The liquid agrochemical according to any one of claims 1 to 3 wherein the content of pyridazine compound is within 5 the range of 4 to 10% by weight.
5. The liquid agrochemical according to any one of claims 1 to 3 wherein the content of pyridazine compound is within the range of 4 to 8% by weight.
6. The liquid agrochemical according to any one of claims 10 1 to 5 wherein the surfactant comprises a combination of a nonionic surfactant(s) and an anionic surfactant(s).
7. The liquid agrochemical according to any one of claims 1 tx> 5 wherein the surfactant(s) comprises dodecylbenzene sulfonate in combination with polyoxyalkylene polyaryl 15 ether or polyoxyalkylene alkyl ether.
8. The liquid agrochemical according to any one of claims 1 to 7 which is an emulsifiable concentrate.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2016-041875 | 2016-03-04 | ||
| JP2016041875A JP6589697B2 (en) | 2016-03-04 | 2016-03-04 | Liquid pesticide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE20170047A1 IE20170047A1 (en) | 2017-12-13 |
| IE86912B1 true IE86912B1 (en) | 2018-08-08 |
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