WO2011157101A1 - Pesticidal composition - Google Patents
Pesticidal composition Download PDFInfo
- Publication number
- WO2011157101A1 WO2011157101A1 PCT/CN2011/074622 CN2011074622W WO2011157101A1 WO 2011157101 A1 WO2011157101 A1 WO 2011157101A1 CN 2011074622 W CN2011074622 W CN 2011074622W WO 2011157101 A1 WO2011157101 A1 WO 2011157101A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- ether
- glycol
- mono
- formulation
- alkyl ether
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 184
- 230000000361 pesticidal effect Effects 0.000 title description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 299
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 150
- 150000005215 alkyl ethers Chemical class 0.000 claims abstract description 117
- XYFMGGWVGACNEC-UHFFFAOYSA-N n-carbamoyl-n-phenylbenzamide Chemical compound C=1C=CC=CC=1N(C(=O)N)C(=O)C1=CC=CC=C1 XYFMGGWVGACNEC-UHFFFAOYSA-N 0.000 claims abstract description 52
- 239000004480 active ingredient Substances 0.000 claims abstract description 51
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 33
- 238000000034 method Methods 0.000 claims abstract description 20
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 5
- 239000012872 agrochemical composition Substances 0.000 claims abstract description 5
- 238000009472 formulation Methods 0.000 claims description 111
- 239000012669 liquid formulation Substances 0.000 claims description 71
- 206010015946 Eye irritation Diseases 0.000 claims description 62
- 231100000013 eye irritation Toxicity 0.000 claims description 62
- 239000005912 Lufenuron Substances 0.000 claims description 21
- PWPJGUXAGUPAHP-UHFFFAOYSA-N lufenuron Chemical compound C1=C(Cl)C(OC(F)(F)C(C(F)(F)F)F)=CC(Cl)=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F PWPJGUXAGUPAHP-UHFFFAOYSA-N 0.000 claims description 21
- 229960000521 lufenuron Drugs 0.000 claims description 21
- 239000004094 surface-active agent Substances 0.000 claims description 18
- 239000005942 Triflumuron Substances 0.000 claims description 15
- RGNPBRKPHBKNKX-UHFFFAOYSA-N hexaflumuron Chemical compound C1=C(Cl)C(OC(F)(F)C(F)F)=C(Cl)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F RGNPBRKPHBKNKX-UHFFFAOYSA-N 0.000 claims description 15
- NJPPVKZQTLUDBO-UHFFFAOYSA-N novaluron Chemical compound C1=C(Cl)C(OC(F)(F)C(OC(F)(F)F)F)=CC=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F NJPPVKZQTLUDBO-UHFFFAOYSA-N 0.000 claims description 15
- YTYGAJLZOJPJGH-UHFFFAOYSA-N noviflumuron Chemical compound FC1=C(Cl)C(OC(F)(F)C(C(F)(F)F)F)=C(Cl)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F YTYGAJLZOJPJGH-UHFFFAOYSA-N 0.000 claims description 15
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 claims description 15
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 14
- 235000014666 liquid concentrate Nutrition 0.000 claims description 14
- 239000005893 Diflubenzuron Substances 0.000 claims description 11
- 239000005938 Teflubenzuron Substances 0.000 claims description 11
- UISUNVFOGSJSKD-UHFFFAOYSA-N chlorfluazuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC(C=C1Cl)=CC(Cl)=C1OC1=NC=C(C(F)(F)F)C=C1Cl UISUNVFOGSJSKD-UHFFFAOYSA-N 0.000 claims description 11
- QQQYTWIFVNKMRW-UHFFFAOYSA-N diflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(Cl)C=C1 QQQYTWIFVNKMRW-UHFFFAOYSA-N 0.000 claims description 11
- 229940019503 diflubenzuron Drugs 0.000 claims description 11
- RYLHNOVXKPXDIP-UHFFFAOYSA-N flufenoxuron Chemical compound C=1C=C(NC(=O)NC(=O)C=2C(=CC=CC=2F)F)C(F)=CC=1OC1=CC=C(C(F)(F)F)C=C1Cl RYLHNOVXKPXDIP-UHFFFAOYSA-N 0.000 claims description 11
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 claims description 11
- -1 alkyl pyrrolidone Chemical compound 0.000 claims description 9
- 239000003995 emulsifying agent Substances 0.000 claims description 9
- 239000002798 polar solvent Substances 0.000 claims description 9
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 claims description 7
- 235000008504 concentrate Nutrition 0.000 claims description 6
- 239000012141 concentrate Substances 0.000 claims description 6
- 239000000839 emulsion Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000003381 stabilizer Substances 0.000 claims description 4
- CUVLMZNMSPJDON-UHFFFAOYSA-N 1-(1-butoxypropan-2-yloxy)propan-2-ol Chemical compound CCCCOCC(C)OCC(C)O CUVLMZNMSPJDON-UHFFFAOYSA-N 0.000 claims description 3
- GDXHBFHOEYVPED-UHFFFAOYSA-N 1-(2-butoxyethoxy)butane Chemical compound CCCCOCCOCCCC GDXHBFHOEYVPED-UHFFFAOYSA-N 0.000 claims description 3
- UOWSVNMPHMJCBZ-UHFFFAOYSA-N 1-[2-(2-butoxypropoxy)propoxy]butane Chemical compound CCCCOCC(C)OCC(C)OCCCC UOWSVNMPHMJCBZ-UHFFFAOYSA-N 0.000 claims description 3
- BOGFHOWTVGAYFK-UHFFFAOYSA-N 1-[2-(2-propoxyethoxy)ethoxy]propane Chemical compound CCCOCCOCCOCCC BOGFHOWTVGAYFK-UHFFFAOYSA-N 0.000 claims description 3
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 claims description 3
- ZIKLJUUTSQYGQI-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxypropoxy)propane Chemical compound CCOCC(C)OCC(C)OCC ZIKLJUUTSQYGQI-UHFFFAOYSA-N 0.000 claims description 3
- JOERQAIRIDZWHX-UHFFFAOYSA-N 1-propoxy-2-(2-propoxypropoxy)propane Chemical compound CCCOCC(C)OCC(C)OCCC JOERQAIRIDZWHX-UHFFFAOYSA-N 0.000 claims description 3
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 claims description 3
- MTVLEKBQSDTQGO-UHFFFAOYSA-N 2-(2-ethoxypropoxy)propan-1-ol Chemical compound CCOC(C)COC(C)CO MTVLEKBQSDTQGO-UHFFFAOYSA-N 0.000 claims description 3
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 claims description 3
- CUDYYMUUJHLCGZ-UHFFFAOYSA-N 2-(2-methoxypropoxy)propan-1-ol Chemical compound COC(C)COC(C)CO CUDYYMUUJHLCGZ-UHFFFAOYSA-N 0.000 claims description 3
- DJCYDDALXPHSHR-UHFFFAOYSA-N 2-(2-propoxyethoxy)ethanol Chemical compound CCCOCCOCCO DJCYDDALXPHSHR-UHFFFAOYSA-N 0.000 claims description 3
- XYVAYAJYLWYJJN-UHFFFAOYSA-N 2-(2-propoxypropoxy)propan-1-ol Chemical compound CCCOC(C)COC(C)CO XYVAYAJYLWYJJN-UHFFFAOYSA-N 0.000 claims description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 3
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 3
- CRWNQZTZTZWPOF-UHFFFAOYSA-N 2-methyl-4-phenylpyridine Chemical compound C1=NC(C)=CC(C=2C=CC=CC=2)=C1 CRWNQZTZTZWPOF-UHFFFAOYSA-N 0.000 claims description 3
- VATRWWPJWVCZTA-UHFFFAOYSA-N 3-oxo-n-[2-(trifluoromethyl)phenyl]butanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C(F)(F)F VATRWWPJWVCZTA-UHFFFAOYSA-N 0.000 claims description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 3
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 claims description 3
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 claims description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 3
- WPPOGHDFAVQKLN-UHFFFAOYSA-N N-Octyl-2-pyrrolidone Chemical compound CCCCCCCCN1CCCC1=O WPPOGHDFAVQKLN-UHFFFAOYSA-N 0.000 claims description 2
- 150000002596 lactones Chemical class 0.000 claims description 2
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims description 2
- 230000000749 insecticidal effect Effects 0.000 claims 3
- 239000003638 chemical reducing agent Substances 0.000 description 29
- 239000002904 solvent Substances 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 13
- 239000002085 irritant Substances 0.000 description 9
- 231100000021 irritant Toxicity 0.000 description 9
- 230000007794 irritation Effects 0.000 description 8
- 239000004495 emulsifiable concentrate Substances 0.000 description 7
- 239000000575 pesticide Substances 0.000 description 7
- 210000003711 chorioallantoic membrane Anatomy 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 239000002917 insecticide Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 4
- 241000238631 Hexapoda Species 0.000 description 4
- 235000013877 carbamide Nutrition 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 4
- 229920000053 polysorbate 80 Polymers 0.000 description 4
- 239000001593 sorbitan monooleate Substances 0.000 description 4
- 235000011069 sorbitan monooleate Nutrition 0.000 description 4
- 229940035049 sorbitan monooleate Drugs 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 239000003093 cationic surfactant Substances 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 239000002736 nonionic surfactant Substances 0.000 description 3
- 230000002110 toxicologic effect Effects 0.000 description 3
- 239000012855 volatile organic compound Substances 0.000 description 3
- 241000532370 Atla Species 0.000 description 2
- 208000032843 Hemorrhage Diseases 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 229920001214 Polysorbate 60 Polymers 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- 230000015271 coagulation Effects 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000009089 cytolysis Effects 0.000 description 2
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 2
- 239000013020 final formulation Substances 0.000 description 2
- 238000002372 labelling Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000002602 strong irritant Substances 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 231100000027 toxicology Toxicity 0.000 description 2
- 230000002792 vascular Effects 0.000 description 2
- QQGRFMIMXPWKPM-UHFFFAOYSA-N 2,3,4-tributylphenol Chemical compound CCCCC1=CC=C(O)C(CCCC)=C1CCCC QQGRFMIMXPWKPM-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- CJRJTCMSQLEPFQ-UHFFFAOYSA-N 6-cat Chemical compound ClC1=CC=C2CC(N)CCC2=C1 CJRJTCMSQLEPFQ-UHFFFAOYSA-N 0.000 description 1
- MOXFIOUBWCCTGC-UHFFFAOYSA-N C(CCCCCCCCCCC)OS(=O)(=O)C1=CC=CC=C1.C(CCCCCCCCCCC)OS(=O)(=O)C1=CC=CC=C1 Chemical compound C(CCCCCCCCCCC)OS(=O)(=O)C1=CC=CC=C1.C(CCCCCCCCCCC)OS(=O)(=O)C1=CC=CC=C1 MOXFIOUBWCCTGC-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- HRYILSDLIGTCOP-UHFFFAOYSA-N N-benzoylurea Chemical compound NC(=O)NC(=O)C1=CC=CC=C1 HRYILSDLIGTCOP-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 1
- 239000004147 Sorbitan trioleate Substances 0.000 description 1
- VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- BCOZLGOHQFNXBI-UHFFFAOYSA-M benzyl-bis(2-chloroethyl)-ethylazanium;bromide Chemical compound [Br-].ClCC[N+](CC)(CCCl)CC1=CC=CC=C1 BCOZLGOHQFNXBI-UHFFFAOYSA-M 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 231100001032 irritation of the eye Toxicity 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000008389 polyethoxylated castor oil Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
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- 231100000759 toxicological effect Toxicity 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical class OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
Definitions
- the present invention relates to an agrochemical composition.
- the present invention is especially concerned with such a composition comprising one or more benzoylphenyl urea compounds active as an insecticide.
- the present invention further relates to a method of preparing the aforementioned composition and their use in crop protection.
- the present invention is particularly concerned with the reduction of eye irritation when using a liquid concentrate based on benzoylphenyl urea insecticide compounds and to compositions exhibiting reduced eye irritation.
- BPU compounds are known in the art for controlling insects.
- examples of such formulations include those with active ingredients selected from among novaluron, lufenuron, hexaflumuron, triflumuron, diflubenzuron, chlorfluazuron, flufenoxuron, noviflumuron and teflubenzuron.
- Benzoylphenyl urea compounds are generally commercialized in emulsifiable concentrate (EC) formulations.
- EC emulsifiable concentrate
- organic solvents such as aromatic hydrocarbons, chlorinated hydrocarbons, etc.
- organic solvents are known for their toxicological and ecotoxicological properties, creating toxicological and ecotoxicological problems.
- Aliphatic hydrocarbons suffer from their generally low solvent power with respect to solid pesticides, leading to difficulties with producing effective and stable formulations.
- the other solvents listed above, while suitable to solubilize the pesticide, are themselves soluble in water.
- Such a solubility in water is a problem when the EC formulation is diluted to prepare a spray for final application and use.
- the solubility in water causes the phenomenon of crystallization of the pesticidally acive ingredient.
- Such crystallization makes the formulation unsuitable for spraying, in particular a a result of blockages forming in the spray equipment, especially in the fine passageways and nozzles of the equipment.
- WO02/45507 describes a microemulsifiable concentrate formulation of a hydrophobic pesticide compound, wherein the active ingredient and at least one surfactant are dissolved in a solvent system comprising a hydrophobic water-insoluble alkylalkanolate as a first solvent and a polyhydric alcohol or a condensate thereof as a second solvent.
- the formulations are reported to exhibit reduced eye irritation.
- PCT/EP2005/07256 discloses liquid concentrate formulations of water-insoluble pesticide compounds having both improved storage and dilution stability.
- the formulations comprise at least one pesticide compound, at least one organic solvent having a water solubility of at least 10g/L and at least one non-ionic block copolymer comprising at least one polyethylene oxide moiety and at least one hydrophobic polyether moiety.
- the problem of eye irritation is not discussed in this document and does not appear to be addressed therein.
- Benzoylphenyl urea (BPU) compounds for example selected from among novaluron, lufenuron, hexaflumuron, triflumuron, diflubenzuron, chlorfluazuron, flufenoxuron, noviflumuron and teflubenzuron, are strong irritants to eyes.
- the commercial benzoylphenyl urea emulsion concentrate formulations exhibit strong irritancy to the eyes, which is caused not only by the solvents and surfactants present in the formulation, but also by the active ingredients present. So even if the solvents and surfactants used are not irritants to the eyes, the formulation nevertheless always exhibits strong irritancy, due to the properties of the active ingredient present.
- the present invention relates to a use of certain C 2 -C 4 dialkylene glycol di-/mono- Ci-C 4 alkyl ethers for reducing the irritancy to eyes of pesticidal formulations, especially reducing the eye irritancy caused by benzoylphenyl urea compounds as active ingredient in agrochemical formulations.
- the present invention provides an agrochemical composition
- a benzoylphenyl urea as active ingredient and a C 2 -C 4 dialkylene glycol di-/mono- C-
- the present invention provides an agrochemical composition
- the composition of the present invention further comprises at least one benzoylphenyl urea active ingredient.
- Suitable benzoylphenyl urea compounds are well known in the art and are commercially available.
- the composition comprises at least one member selected from the group consisting of novaluron, lufenuron, hexaflumuron, triflumuron, diflubenzuron, chlorfluazuron, flufenoxuron, noviflumuron and teflubenzuron.
- the composition may comprise further components, as known in the art.
- the composition optionally comprises at least one member selected from the group consisting of a surface-active agent, an organic polar solvent and a low temperature stabilizer. Suitable surface-active agents, organic polar solvents and stabilizers are known in the art and are commercially available.
- the present invention also provides, in a further aspect, a practical method for preparing an agriculturally acceptable, stable liquid concentrate formulation, the method comprising combining one or more benzoylphenyl urea active ingredients with a solvent is selected from one or more C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ethers.
- the present invention provides the use of a C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether to reduce the eye irritancy of a benzoylphenyl urea, in particular when used as active ingredient in a pesticidal formulation.
- the present invention provides the use of a composition as hereinbefore described in the control of pests, in particular insects.
- the present invention also provides a method of controlling pests, in particular insects, at a locus, the method comprising applying to the locus a composition as hereinbefore described.
- Benzoylphenyl ureas are water-insoluble compounds, and such compounds are strong irritants to eyes. These compounds are commercially formulated into liquid concentrates. Many organic solvents used in Emulsion Concentrate are irritants to eyes. A major problem associated with liquid concentrate formulations is that they may cause irritation to eyes.
- C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ethers are not only non-irritant to eyes, but also can reduce the irritancy of certain active ingredients, in particular of benzoylphenyl urea to eyes in the final formulation.
- -C 4 alkyl ether is present in the composition in an amount sufficient to reduce the eye irritation of benzoylphenyl urea active ingredient.
- the C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether is effective in reducing the eye irritation of the benzoylphenyl urea active ingredient compounds.
- the inclusion of one or more C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ethers in liquid concentrates reduces the eye irritancy of the formulation.
- the use of C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ethers in liquid concentrate pesticidal formulations is environmental friendly.
- the C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ethers are suitable for preparing water-dilutable, liquid concentrate formulations of sparingly water-soluble, or even water-insoluble, organic pesticide compounds such as benzoylphenyl ureas and, in particular, for reducing the risk of eye irritation caused by liquid insecticide formulations of such pesticide compounds.
- the one or more C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ethers are present in an amount sufficient to reduce eye irritation of the benzoylphenyl urea compounds.
- the amount of the C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether required to be present will depend upon such factors as the concentration of the benzoylphenyl urea active ingredient and the particular benzoylphenyl urea or ureas present in the formulation.
- the amount of the C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether required to reduce or eliminate the irritancy to eyes of the formulation may be determined without undue experimentation by the skilled person, for example by trial and error.
- the C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether is preferably present in an amount such as to give a weight ratio of the benzoylphenyl urea active ingredient to the C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether of at least 1 : 1 , more preferably at least 1 : 1 .5, still more preferably of at least 1 :2, especially of at least 1 :3.
- the C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether is preferably present in an amount such as to give a weight ratio of the benzoylphenyl urea active ingredient to the C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether of from 1 : 1 to 1 :30, more preferably from 1 :2 to 1 :20, still more preferably from 1 :3 to 1 : 15.
- the composition may comprise a single C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether or a combination of two or more C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ethers.
- the C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether is at least one member selected from the group consisting of diethylene glycol dimethyl ether, diethylene glycol methyl ether, dipropylene glycol dimethyl ether, dipropylene glycol methyl ether, dibutylene glycol dimethyl ether, dibutylene glycol methyl ether, diethylene glycol diethyl ether, diethylene glycol ethyl ether, dipropylene glycol diethyl ether, dipropylene glycol ethyl ether, dibutylene glycol diethyl ether, dibutylene glycol ethyl ether, diethylene glycol dipropyl ether, diethylene glycol propyl ether, dipropylene glycol dipropyl ether, dipropylene glycol propyl ether, dibutylene glycol dipropyl ether, dibutylene glycol propylene glycol propyl ether, di
- the composition of the present invention may be prepared in any suitable form.
- the composition of the present invention is preferably a liquid concentrate, in particular an emulsion concentrate (EC) formulation.
- EC emulsion concentrate
- the relative amount of C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether present in the composition will depend upon the amount, number and nature of the other components of the composition.
- the one or more C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ethers may be present in an amount of at least 10% by weight, preferably at least 20% by weight, more preferably at least 30% by weight, especially at least 35% by weight.
- the C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether may be present in the composition in an amount of from 2 to 90% by weight, preferably from 5 to 80% be weight, more preferably from 10 to 75% by weight.
- An amount of C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether in the range of from 35 to 75% by weight has been found to be particularly suitable in many embodiments.
- C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ethers are effective in reducing the irritancy to eyes of certain benzoylphenyl urea derivatives as active agrochemicals, in particular insecticides.
- the composition may comprise one or a combination or two or more benzoylphenyl urea derivatives as active ingredient.
- the formulation contains as active ingredient a benzoylphenyl urea selected from the group consisting of novaluron, lufenuron, hexaflumuron, triflumuron, diflubenzuron, chlorfluazuron, flufenoxuron, noviflumuron, teflubenzuron and mixtures thereof.
- a benzoylphenyl urea selected from the group consisting of novaluron, lufenuron, hexaflumuron, triflumuron, diflubenzuron, chlorfluazuron, flufenoxuron, noviflumuron, teflubenzuron and mixtures thereof.
- the benzoylphenyl urea active ingredient may be present in any suitable amount.
- the benzoylphenyl urea is present in an amount of at least 2% by weight, more preferably at least 3% by weight, still more preferably at least 5% by weight.
- the benzoylphenyl urea may be present in an amount in the range of from 2 to 50% by weight, preferably in the range of from 3 to 45% by weight, more preferably from 4 to 40%) by weight.
- An amount of benzoyl urea in the range of from 5 to 35% by weight has been found to be particularly suitable in many embodiments.
- compositions of the present invention may comprise other components as is known in the art.
- Such further components include, for example one or more organic polar solvents and emulsifiers. Suitable components are known in the art and are commercially available.
- Suitable organic polar solvents include one or more alcohols, such as benzyl alcohol, one or more alkyl pyrrolidones, such as N-methylprrolidone, N-octylpyrrolidone, or one or more lactones, such as ⁇ -butyrolactone.
- suitable solvents will be known to the person skilled in the art.
- the solvent may be present in any suitable amount. In particular, the solvent may be present in an amount in the range of from 10 to 90% by weight of the composition, preferably from 15 to 75% by weight, more preferably from 20 to 60% by weight.
- the surfactant is one in which the lipophillic moiety is derived from a safe natural product.
- Such surfactants are usually found in use in food and cosmetic industries.
- the preferred surfactants for use in the compositions of the present invention are those with an H.L.B range of from 7 to 17.
- suitable surface-active compounds are nonionic, cationic and/or anionic surfactants or a mixture of such surfactants, the surfactant or surfactant mixture having good emulsifying, dispersing and wetting capabilities.
- Preferred nonionic surfactants are polyethoxylated castor oil, polyadducts of polypropylene and polyethylene oxide, tributylphenol polyethoxylate, polyethylene glycol and octylphenol polyethoxylate.
- Fatty acid esters of polyoxyethylene sorbitan, e.g. polyoxyethylene sorbitan trioleate, are also suitable nonionic surfactants.
- Preferred cationic surfactants for inclusion in the composition of the present invention include quaternary ammonium salts carrying, as N-substituent, at least one C 8 -C 2 2 alkyi radical and, as a further substituent, unsubstituted or halogenated lower alkyi, benzyl or hydroxyl- lower alkyi radicals.
- the salts are preferably in the form of halide, methyl sulfate or ethyl sulfate.
- Examples of such cationic surfactants are stearyltrimethylammonium chloride and benzyl bis(2-chloroethyl)ethylammonium bromide.
- Suitable anionic surfactants for use in the compositions include water-soluble soaps as well as water-soluble synthetic surface-active compounds, alkylarylsulfonates.
- alkylarylsulfonates are sodium, calcium or triethanolammonium salt of dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid or a condensate of naphthalenesulfonic acid and formaldehyde.
- Corresponding phosphates for example salts of phosphoric acid ester of an adduct of p-nonylphenol with 4 to 14 mol of ethylene oxide, or phospholipids, are also suitable.
- the surfactant or surfactant mixture may be present in the composition in any suitable amount.
- the surfactant is present in an amount in the range of from 5 to 40% by weight, more preferably from 5 to 35% by weight, still more preferably from 10 to 30% by weight.
- a surfactant concentration of from 20 to 30% by weight has been found to be particularly suitable in many embodiments.
- compositions for inclusion in the composition are well known in the art and include, for example a stabilizer and a thickener. Such components are commercially available and their use will be recognized and understood by the person skilled in the art.
- the present invention provides a liquid concentrate comprising a benzoylphenyl urea and a C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether.
- the present invention provides the use of a C 2 -C 4 dialkylene glycol di-/mono- C-
- compositions of the present invention may be prepared using techniques known in the art.
- a particularly preferred method of preparing the composition is as follows:
- Each component is added according to the weight fraction required in the final composition.
- the solvent as required, and one or more C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ethers are charged to a suitable mixing vessel, for example a blending tank.
- the resulting mixture is agitated.
- the one or more benzoylphenyl urea derivatives are added to the mixture and the agitation continues until the benzoylphenyl urea derivatives are dissolved completely in the solvent.
- An agitation time of about 30 minutes is typical.
- further components such as an emulsifier, if present, are added and the mixture is further agitated to ensure homogeneity.
- a further agitation time of about 1 hour is typical.
- the present invention provides a method of reducing the eye irritation of insecticide liquid formulations comprising benzoylphenyl urea derivative, comprising adding a C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether, preferably those C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ethers hereinbefore recited, to the formulation in an amount sufficient to reduce the eye irritancy of the benzoylphenyl urea derivative.
- test samples were categorized as follows:
- compositions according to the present invention prepared and tested as described above, are described in the following examples, in conjunction with comparative test results given in respective tables.
- Example 1 The liquid formulation described in Table 1 was prepared containing the indicated
- Example 1 contained C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether in an amount of 65%wt.
- Table 1 describes the liquid formulation of Example 1 and the comparison formulation, Comparison A.
- the liquid formulation described in Table 2 was prepared containing the indicated C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether and novaluron as active ingredient, wherein the ratio of novaluron and C 2 -C 4 dialkylene glycol di-/mono- C1-C4 alkyl ether was approximately 1 :6. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without a C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether as eye irritation reducer.
- Example 2 contained the indicated C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether in an amount of 60%wt. Table 2 describes the liquid formulation of Example 2 and the comparison formulation, Comparison B.
- the liquid formulation described in Table 3 was prepared containing the indicated C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether and hexaflumuron as active ingredient, wherein the ratio of hexaflumuron and C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether was approximately 1 :7.25. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C 2 -C 4 dialkylene glycol di-/mono- Ci-C 4 alkyl ether as eye irritancy reducer.
- Example 3 contained C 2 -C 4 dialkylene glycol di-/mono- Ci-C 4 alkyl ether in an amount of 58%wt. Table 3 describes the liquid formulation of Example 3 and the comparison formulation, Comparison C.
- the liquid formulation described in Table 4 was prepared containing the indicated C2-C4 dialkylene glycol di-/mono- C1-C4 alkyl ether and triflumuron as active ingredient, wherein the ratio of triflumuron and C 2 -C 4 dialkylene glycol di-/mono- C1-C4 alkyl ether was approximately 1 : 12. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C 2 -C 4 dialkylene glycol di-/mono- C1-C4 alkyl ether as eye irritation reducer.
- Example 4 contained C 2 -C 4 dialkylene glycol di-/mono- C1-C4 alkyl ether in an amount of 60%wt. Table 4 describes the liquid formulation of Example 4 and the comparison formulation, Comparison D. Table 4
- the liquid formulation described in Table 5 was prepared containing the indicated C2-C4 dialkylene glycol di-/mono- C1-C4 alkyl ether and diflubenzuron as active ingredient, wherein the ratio of diflubenzuron and C 2 -C 4 dialkylene glycol di-/mono- C1-C4 alkyl ether was approximately 1 :6. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C 2 -C 4 dialkylene glycol di-/mono- C -C 4 alkyl ether eye irritation reducer.
- Example 5 contained the C 2 -C 4 dialkylene glycol di-/mono- ( C 4 alkyl ether in an amount of 60%wt. Table 5 describes the liquid formulation of Example 5 and the comparison formulation, Comparison E.
- the liquid formulation described in Table 6 was prepared containing the indicated C 2 -C 4 dialkylene glycol di-/mono- C1-C4 alkyl ether and chlorfluazuron as active ingredient, wherein the ratio of chlorfluazuron and C 2 -C 4 dialkylene glycol di-/mono- C1-C4 alkyl ether was approximately 1 :2. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C 2 -C 4 dialkylene glycol di-/mono- ( C 4 alkyl ether as eye irritation reducer.
- Example 6 contained the C 2 -C 4 dialkylene glycol di-/mono- C1-C4 alkyl ether in an amount of 40%wt. Table 6 describes the liquid formulation of Example 6 and the comparison formulation, Comparison F.
- the liquid formulation described in Table 7 was prepared containing the indicated C 2 -C 4 dialkylene glycol di-/mono- C1-C4 alkyl ether and flufenoxuron as the active ingreduent, wherein the ratio of flufenoxuron and the C 2 -C 4 dialkylene glycol di-/mono- C1-C4 alkyl ether was approximately 1 : 1 .6. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C 2 -C 4 dialkylene glycol di-/mono- ( C 4 alkyl ether as eye irritation reducer.
- Example 7 contained the C 2 -C 4 dialkylene glycol di-/mono- C1-C4 alkyl ether in an amount of 40%wt. Table 7 describes the liquid formulation of Example 7 and the comparison formulation, Comparison G.
- the liquid formulation described in Table 8 was prepared containing the indicated C 2 -C 4 dialkylene glycol di-/mono- C1-C4 alkyl ether and noviflumuron as the active ingredient, wherein the ratio of noviflumuron and C 2 -C 4 dialkylene glycol di-/mono- C1-C4 alkyl ether was approximately 1 : 12. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C 2 -C 4 dialkylene glycol di-/mono- ( C 4 alkyl ether as eye irritation reducer.
- Example 8 contained the C 2 -C 4 dialkylene glycol di-/mono- C1-C4 alkyl ether in an amount of 60%wt. Table 8 describes the liquid formulation of Example 8 and the comparison formulation, Comparison H.
- the liquid formulation described in Table 9 was prepared containing the indicated C 2 -C 4 dialkylene glycol di-/mono- C1-C4 alkyl ether and teflubenuron as the active ingredient, wherein the ratio of teflubenuron and the C 2 -C 4 dialkylene glycol di-/mono- C1-C4 alkyl ether was approximately 1 : 15. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C 2 -C 4 dialkylene glycol di-/mono- ( C 4 alkyl ether as eye irritation reducer.
- Example 9 contained the C 2 -C 4 dialkylene glycol di-/mono- C1-C4 alkyl ether in an amount of 60%wt. Table 9 describes the liquid formulation of Example 9 and the comparison formulation, Comparison I.
- EXAMPLE 9 teflubenuron EC (with : COMPARISON I: teflubenuron EC Remark eye irritation reducer) (without irritation reducer)
- teflubenuron tech 40kg ( as ; teflubenuron tech 40kg ( as Active pure) pure) ingredient
- the liquid formulation described in Table 10 was prepared containing the indicated C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether and a combination of novaluron and lufenuron as active ingredients, wherein the ratio of novaluron plus lufenuron and the C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether was approximately 1 :6. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether as eye irritation reducer.
- Example 10 contained the C 2 -C 4 dialkylene glycol di-/mono-
- Ci-C 4 alkyl ether in an amount of 60%wt.
- Table 10 describes the liquid formulation of Example 10 and the comparison formulation, Comparison J.
- the liquid formulation described in Table 11 was prepared containing the indicated C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether and a combination of triflumuron and hexaflumuron as active ingredients, wherein the ratio of triflumuron plus hexaflumuron and the C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether was approximately 1 :2.5. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether as eye irritation reducer.
- Example 11 contained the C 2 -C 4 dialkylene glycol di-/mono-
- Ci-C 4 alkyl ether in an amount of 50%wt.
- Table 11 describes the liquid formulation of Example 11 and the comparison formulation, Comparison K.
- the liquid formulation described in Table 12 was prepared containing the indicated C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether and a combination of diflubenzuron and chlorfluazuron as active ingredients, wherein the ratio of diflubenzuron plus chlorfluazuron and the C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether was approximately 1 :2.75. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether as eye irritation reducer.
- Example 12 contained the C 2 -C 4 dialkylene glycol di-/mono-
- Ci-C 4 alkyl ether in an amount of 55%wt.
- Table 1 describes the liquid formulation of Example 12 and the comparison formulation, Comparison L.
- the liquid formulation described in Table 13 was prepared containing the indicated C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether and a combination of flufenoxuron and noviflumuron as active ingredients, wherein the ratio of flufenoxuron plus noviflumuron and the C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether was approximately 1 : 1 .4. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether as eye irritation reducer.
- Example 13 contained the C 2 -C 4 dialkylene glycol di-/mono-
- Ci-C 4 alkyl ether in an amount of 35%wt.
- Table 13 describes the liquid formulation of Example 1 and the comparison formulation, Comparison M.
- the liquid formulation described in Table 1 was prepared containing the indicated C 2 -C 4 dialkylene glycol di-/mono- C 1 -C4 alkyl ether and a combination of noviflumuron and teflubenzuron as active ingredients, wherein the ratio of noviflumuron plus teflubenzuron and the C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether was approximately 1 : 1 .3. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether as eye irritation reducer.
- Example 14 contained the C 2 -C 4 dialkylene glycol di-/mono-
- Ci-C 4 alkyl ether in an amount of 40%wt.
- Table 14 describes the liquid formulation of Example 14 and the comparison formulation, Comparison N.
- the liquid formulation described in Table 15 was prepared containing the indicated C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether and a combination of novaluron and hexaflumuron as active ingredients, wherein the ratio of novaluron plus hexaflumuron and C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether was approximately 1 :6. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether as eye irritation reducer.
- Example 15 contained the C 2 -C 4 dialkylene glycol di-/mono-
- Ci-C 4 alkyl ether in an amount of 65%wt.
- Table 15 describes the liquid formulation of Example 15 and the comparison formulation, Comparison O.
- EXAMPLE 15 COMPARISON O: Remark novaluron+hexaflumuron EC (with eye I novaluron+hexaflumuron EC (without
- Component Composition I Component Composition
- TWEEN 80 100kg TWEEN 80 100kg Emulsifier
- the liquid formulation described in Table 16 was prepared containing the indicated C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether and a combination of lufenuron and triflumuron as active ingredients, wherein the ratio of lufenuron plus triflumuron and C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether was approximately 1 :2.9. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether as eye irritation reducer.
- Example 16 contained the C 2 -C 4 dialkylene glycol di-/mono- Ci-C 4 alkyl ether in an amount of 52%wt. Table 16 describes the liquid formulation of Example 16 and the comparison formulation, Comparison P.
- the liquid formulation described in Table 17 was prepared containing the indicated C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether and a combination of lufenuron and diflubenzuron as active ingredients, wherein the ratio of lufenuron plus diflubenzuron and C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether was approximately 1 : 1 .8. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether as eye irritation reducer.
- Example 17 contained the C 2 -C 4 dialkylene glycol di-/mono-
- Ci-C 4 alkyl ether in an amount of 45%wt.
- Table 17 describes the liquid formulation of Example 17 and the comparison formulation, Comparison Q.
- the liquid formulation described in Table 18 was prepared containing the indicated C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether and a combination of lufenuron and chlorfluazuron as active ingredients, wherein the ratio of lufenuron plus chlorfluazuron and C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether was approximately 1 : 1 .4. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether as eye irritation reducer.
- Example 18 contained the C 2 -C 4 dialkylene glycol di-/mono-
- Ci-C 4 alkyl ether in an amount of 65%wt.
- Table 18 describes the liquid formulation of Example 18 and the comparison formulation, Comparison R.
- the liquid formulation described in Table 19 was prepared containing the indicated C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether and a combination of lufenuron and flufenoxuron as active ingredients, wherein the ratio of lufenuron plus flufenoxuron and C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether was approximately 1 :7. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether as eye irritation reducer.
- Example 19 contained the C 2 -C 4 dialkylene glycol di-/mono-
- Ci-C 4 alkyl ether in an amount of 70%wt.
- Table 19 describes the liquid formulation of Example 19 and the comparison formulation, Comparison S.
- the liquid formulation described in Table 20 was prepared containing the indicated C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether and a combination of lufenuron and noviflumuron as active ingredients, wherein the ratio of lufenuron plus noviflumuron and C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether was approximately 1 : 1. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether as eye irritation reducer.
- Example 20 contained the C 2 -C 4 dialkylene glycol di-/mono-
- Ci-C 4 alkyl ether in an amount of 35%wt.
- Table 20 describes the liquid formulation of Example 20 and the comparison formulation, Comparison T.
- the liquid formulation described in Table 21 was prepared containing the indicated C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether and a combination of lufenuron and teflubenzuron as active ingredients, wherein the ratio of lufenuron plus teflubenzuron and C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether was approximately 1 :6. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether as eye irritation reducer.
- Example 1 contained the C 2 -C 4 dialkylene glycol di-/mono-
- Ci-C 4 alkyl ether in an amount of 60%wt.
- Table 21 describes the liquid formulation of Example 21 and the comparison formulation, Comparison U.
- the liquid formulation described in Table 22 was prepared containing the indicated C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether and a combination of triflumuron and teflubenzuron as active ingredient, wherein the ratio of triflumuron plus teflubenzuron and the C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether was approximately 1 :2. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether as eye irritation reducer.
- Example 22 contained the C 2 -C 4 dialkylene glycol di-/mono-
- Ci-C 4 alkyl ether in an amount of 40%wt.
- Table 22 describes the liquid formulation of Example 22 and the comparison formulation, Comparison V.
- the liquid formulation described in Table 23 was prepared containing the indicated C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether and a combination of triflumuron and noviflumuron as active ingredients, wherein the ratio of triflumuron plus noviflumuron and C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether was approximately 1 :3.3. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C 2 -C 4 dialkylene glycol di-/mono- C C 4 alkyl ether as eye irritation reducer.
- Example 23 contained the C 2 -C 4 dialkylene glycol di-/mono-
- Ci-C 4 alkyl ether in an amount of 50%wt.
- Table 23 describes the liquid formulation of Example 23 and the comparison formulation, Comparison 23.
- test samples are categorized as follows:
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Abstract
An agrochemical composition comprising a C2-C4 dialkylene glycol di-/mono- C1-C4 alkyl ether is provided. A method of controlling pests at a locus using the composition and a use of the C2-C4 dialkylene glycol di-/mono- C1-C4 alkyl ether in reducing the eye irritancy of benzoylphenyl urea active ingredients are also provided.
Description
PESTICIDAL COMPOSITION
FIELD OF THE INVENTION The present invention relates to an agrochemical composition. The present invention is especially concerned with such a composition comprising one or more benzoylphenyl urea compounds active as an insecticide. The present invention further relates to a method of preparing the aforementioned composition and their use in crop protection. The present invention is particularly concerned with the reduction of eye irritation when using a liquid concentrate based on benzoylphenyl urea insecticide compounds and to compositions exhibiting reduced eye irritation.
BACKGROUND OF THE INVENTION Insect growth regulator formulations comprising one or more benzoylphenyl urea
(BPU) compounds are known in the art for controlling insects. Examples of such formulations include those with active ingredients selected from among novaluron, lufenuron, hexaflumuron, triflumuron, diflubenzuron, chlorfluazuron, flufenoxuron, noviflumuron and teflubenzuron.
Benzoylphenyl urea compounds are generally commercialized in emulsifiable concentrate (EC) formulations. However, such formulations require substantial quantities of organic solvents such as aromatic hydrocarbons, chlorinated hydrocarbons, etc. for effective formulation of the active ingredient. However, such organic solvents are known for their toxicological and ecotoxicological properties, creating toxicological and ecotoxicological problems.
As a result, the United States Enviromental Protection Agency has a review of ingredients in pesticidal formulations in addition to the active ingredients present. In Europe, the E.E.C. Council is at an advanced stage of introducing legislation for
regulating the use of volatile organic compounds (VOC) and will shortly require an eco-labelling of formulations which contain such VOCs. Further, Canada and Germany already have a system of ecotoxic labelling.
To overcome the need to use such aromatic or chlorinated hydrocarbons, alternative solvents have been tried for use in commercial formulations, with a view to reducing the toxicological effects of the solvent components of the formulations. Examples of such alternative solvents are aliphatic hydrocarbons, alcohols, glycols, polyglycols, glycol ethers, and ketones, as well as polar solvents with a high solvent power, such as gamma-butyrolactone, N-methyl pyrrolidone and the like.
Aliphatic hydrocarbons suffer from their generally low solvent power with respect to solid pesticides, leading to difficulties with producing effective and stable formulations. The other solvents listed above, while suitable to solubilize the pesticide, are themselves soluble in water. Such a solubility in water is a problem when the EC formulation is diluted to prepare a spray for final application and use. The solubility in water causes the phenomenon of crystallization of the pesticidally acive ingredient. Such crystallization makes the formulation unsuitable for spraying, in particular a a result of blockages forming in the spray equipment, especially in the fine passageways and nozzles of the equipment.
Attempts to solve the aforementioned problems are known in the art.
For example, WO02/45507 describes a microemulsifiable concentrate formulation of a hydrophobic pesticide compound, wherein the active ingredient and at least one surfactant are dissolved in a solvent system comprising a hydrophobic water-insoluble alkylalkanolate as a first solvent and a polyhydric alcohol or a condensate thereof as a second solvent. The formulations are reported to exhibit reduced eye irritation.
PCT/EP2005/07256 discloses liquid concentrate formulations of water-insoluble pesticide compounds having both improved storage and dilution stability. The formulations comprise at least one pesticide compound, at least one organic solvent
having a water solubility of at least 10g/L and at least one non-ionic block copolymer comprising at least one polyethylene oxide moiety and at least one hydrophobic polyether moiety. The problem of eye irritation is not discussed in this document and does not appear to be addressed therein.
The solvent mixtures and surfactants disclosed in the prior publications do not offer a solution for all needs. Benzoylphenyl urea (BPU) compounds, for example selected from among novaluron, lufenuron, hexaflumuron, triflumuron, diflubenzuron, chlorfluazuron, flufenoxuron, noviflumuron and teflubenzuron, are strong irritants to eyes. The commercial benzoylphenyl urea emulsion concentrate formulations exhibit strong irritancy to the eyes, which is caused not only by the solvents and surfactants present in the formulation, but also by the active ingredients present. So even if the solvents and surfactants used are not irritants to the eyes, the formulation nevertheless always exhibits strong irritancy, due to the properties of the active ingredient present.
There is an ongoing need to find safe, preferably substantially inert, components for use in liquid concentrate formulations, which are not only themselves non-irritant to eyes, but preferably also can act to reduce the irritancy to eyes of the active ingredients present, in particular benzoylphenyl urea (BPU) compounds.
It has now been surprisingly found that certain C2-C4 dialkylene glycol di-/mono- C C4 alkyl ethers are not only non-irritants to the eyes, but also it can reduce the irritation of the eyes arising from benzoylphenyl urea compounds in the final formulation.
SUMMARY OF THE INVENTION
The present invention relates to a use of certain C2-C4 dialkylene glycol di-/mono- Ci-C4 alkyl ethers for reducing the irritancy to eyes of pesticidal formulations, especially reducing the eye irritancy caused by benzoylphenyl urea compounds as
active ingredient in agrochemical formulations.
Accordingly, in a first aspect, the present invention provides an agrochemical composition comprising a benzoylphenyl urea as active ingredient and a C2-C4 dialkylene glycol di-/mono- C-|-C4 alkyl ether.
It has been found that the presence of one or more C2-C4 dialkylene glycol di-/mono- C-|-C4 alkyl ethers in a formulation comprising one or more benzoylphenyl ureas as active ingredient significantly reduces the toxicity of the formulation, in particular reducing the irritancy of the formulation to the eyes. It is believed that the C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether reduces or substantially negates the irritancy of the benzoylphenyl urea to the eyes.
More preferably, in the first aspect, the present invention provides an agrochemical composition comprising a C2-C4 dialkylene glycol di-/mono- C-|-C4 alkyl ether selected from the group consisting of diethylene glycol dimethyl ether, diethylene glycol methyl ether, dipropylene glycol dimethyl ether, dipropylene glycol methyl ether, dibutylene glycol dimethyl ether, dibutylene glycol methyl ether, diethylene glycol diethyl ether, diethylene glycol ethyl ether, dipropylene glycol diethyl ether, dipropylene glycol ethyl ether, dibutylene glycol diethyl ether, dibutylene glycol ethyl ether, diethylene glycol dipropyl ether, diethylene glycol propyl ether, dipropylene glycol dipropyl ether, dipropylene glycol propyl ether, dibutylene glycol dipropyl ether, dibutylene glycol propyl ether, diethylene glycol dibutyl ether, diethylene glycol butyl ether, dipropylene glycol dibutyl ether, dipropylene glycol butyl ether, dibutylene glycol dibutyl ether, dibutylene glycol butyl ether and mixtures thereof.
As noted above, the composition of the present invention further comprises at least one benzoylphenyl urea active ingredient. Suitable benzoylphenyl urea compounds are well known in the art and are commercially available. Preferably, the composition comprises at least one member selected from the group consisting of novaluron, lufenuron, hexaflumuron, triflumuron, diflubenzuron, chlorfluazuron, flufenoxuron, noviflumuron and teflubenzuron.
The composition may comprise further components, as known in the art. Preferably, the composition optionally comprises at least one member selected from the group consisting of a surface-active agent, an organic polar solvent and a low temperature stabilizer. Suitable surface-active agents, organic polar solvents and stabilizers are known in the art and are commercially available.
The present invention also provides, in a further aspect, a practical method for preparing an agriculturally acceptable, stable liquid concentrate formulation, the method comprising combining one or more benzoylphenyl urea active ingredients with a solvent is selected from one or more C2-C4 dialkylene glycol di-/mono- C C4 alkyl ethers.
Further, the present invention provides the use of a C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether to reduce the eye irritancy of a benzoylphenyl urea, in particular when used as active ingredient in a pesticidal formulation.
In a further aspect, the present invention provides the use of a composition as hereinbefore described in the control of pests, in particular insects.
In still a further aspect, the present invention also provides a method of controlling pests, in particular insects, at a locus, the method comprising applying to the locus a composition as hereinbefore described. DETAILED DESCRIPTION OF THE INVENTION
Benzoylphenyl ureas are water-insoluble compounds, and such compounds are strong irritants to eyes. These compounds are commercially formulated into liquid concentrates. Many organic solvents used in Emulsion Concentrate are irritants to eyes. A major problem associated with liquid concentrate formulations is that they may cause irritation to eyes.
In the present invention it has been surprisingly found that certain C2-C4 dialkylene glycol di-/mono- C C4 alkyl ethers are not only non-irritant to eyes, but also
can reduce the irritancy of certain active ingredients, in particular of benzoylphenyl urea to eyes in the final formulation. The C2-C4 dialkylene glycol di-/mono- C-|-C4 alkyl ether is present in the composition in an amount sufficient to reduce the eye irritation of benzoylphenyl urea active ingredient.
It has been found that the C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether is effective in reducing the eye irritation of the benzoylphenyl urea active ingredient compounds. Thus, the inclusion of one or more C2-C4 dialkylene glycol di-/mono- C C4 alkyl ethers in liquid concentrates reduces the eye irritancy of the formulation. In addition, it has been found that the use of C2-C4 dialkylene glycol di-/mono- C C4 alkyl ethers in liquid concentrate pesticidal formulations is environmental friendly.
The C2-C4 dialkylene glycol di-/mono- C C4 alkyl ethers are suitable for preparing water-dilutable, liquid concentrate formulations of sparingly water-soluble, or even water-insoluble, organic pesticide compounds such as benzoylphenyl ureas and, in particular, for reducing the risk of eye irritation caused by liquid insecticide formulations of such pesticide compounds. The one or more C2-C4 dialkylene glycol di-/mono- C C4 alkyl ethers are present in an amount sufficient to reduce eye irritation of the benzoylphenyl urea compounds. The amount of the C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether required to be present will depend upon such factors as the concentration of the benzoylphenyl urea active ingredient and the particular benzoylphenyl urea or ureas present in the formulation. The amount of the C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether required to reduce or eliminate the irritancy to eyes of the formulation may be determined without undue experimentation by the skilled person, for example by trial and error.
The C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether is preferably present in an amount such as to give a weight ratio of the benzoylphenyl urea active ingredient to the C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether of at least 1 : 1 , more preferably at least 1 : 1 .5, still more preferably of at least 1 :2, especially of at least 1 :3. In particular, the C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether is preferably present
in an amount such as to give a weight ratio of the benzoylphenyl urea active ingredient to the C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether of from 1 : 1 to 1 :30, more preferably from 1 :2 to 1 :20, still more preferably from 1 :3 to 1 : 15.
The composition may comprise a single C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether or a combination of two or more C2-C4 dialkylene glycol di-/mono- C C4 alkyl ethers.
According to a preferred embodiment of the present invention, the C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether is at least one member selected from the group consisting of diethylene glycol dimethyl ether, diethylene glycol methyl ether, dipropylene glycol dimethyl ether, dipropylene glycol methyl ether, dibutylene glycol dimethyl ether, dibutylene glycol methyl ether, diethylene glycol diethyl ether, diethylene glycol ethyl ether, dipropylene glycol diethyl ether, dipropylene glycol ethyl ether, dibutylene glycol diethyl ether, dibutylene glycol ethyl ether, diethylene glycol dipropyl ether, diethylene glycol propyl ether, dipropylene glycol dipropyl ether, dipropylene glycol propyl ether, dibutylene glycol dipropyl ether, dibutylene glycol propyl ether, diethylene glycol dibutyl ether, diethylene glycol butyl ether, dipropylene glycol dibutyl ether, dipropylene glycol butyl ether, dibutylene glycol dibutyl ether, dibutylene glycol butyl ether and mixtures thereof.
The composition of the present invention may be prepared in any suitable form. The composition of the present invention is preferably a liquid concentrate, in particular an emulsion concentrate (EC) formulation. The relative amount of C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether present in the composition will depend upon the amount, number and nature of the other components of the composition. In particular, the one or more C2-C4 dialkylene glycol di-/mono- C C4 alkyl ethers may be present in an amount of at least 10% by weight, preferably at least 20% by weight, more preferably at least 30% by weight, especially at least 35% by weight. The C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether may be present in the composition in an amount of from 2 to 90% by weight, preferably from 5 to 80% be weight, more
preferably from 10 to 75% by weight. An amount of C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether in the range of from 35 to 75% by weight has been found to be particularly suitable in many embodiments.
As noted above, it has been found that C2-C4 dialkylene glycol di-/mono- C C4 alkyl ethers are effective in reducing the irritancy to eyes of certain benzoylphenyl urea derivatives as active agrochemicals, in particular insecticides. The composition may comprise one or a combination or two or more benzoylphenyl urea derivatives as active ingredient.
In one embodiment, the formulation contains as active ingredient a benzoylphenyl urea selected from the group consisting of novaluron, lufenuron, hexaflumuron, triflumuron, diflubenzuron, chlorfluazuron, flufenoxuron, noviflumuron, teflubenzuron and mixtures thereof.
The benzoylphenyl urea active ingredient may be present in any suitable amount. Preferably, the benzoylphenyl urea is present in an amount of at least 2% by weight, more preferably at least 3% by weight, still more preferably at least 5% by weight. The benzoylphenyl urea may be present in an amount in the range of from 2 to 50% by weight, preferably in the range of from 3 to 45% by weight, more preferably from 4 to 40%) by weight. An amount of benzoyl urea in the range of from 5 to 35% by weight has been found to be particularly suitable in many embodiments.
In addition to one or more C2-C4 dialkylene glycol di-/mono- C C4 alkyl ethers and one or more benzoylphenyl urea derivative active ingredients, the compositions of the present invention may comprise other components as is known in the art. Such further components include, for example one or more organic polar solvents and emulsifiers. Suitable components are known in the art and are commercially available.
Suitable organic polar solvents include one or more alcohols, such as benzyl alcohol, one or more alkyl pyrrolidones, such as N-methylprrolidone, N-octylpyrrolidone, or one or more lactones, such as γ-butyrolactone. Other suitable solvents will be known to the person skilled in the art.
The solvent may be present in any suitable amount. In particular, the solvent may be present in an amount in the range of from 10 to 90% by weight of the composition, preferably from 15 to 75% by weight, more preferably from 20 to 60% by weight.
In order that the formulations of the present invention retain their ecological acceptability, it is preferable to include one or more surfactants in the composition. Preferably, the surfactant is one in which the lipophillic moiety is derived from a safe natural product. Such surfactants are usually found in use in food and cosmetic industries. The preferred surfactants for use in the compositions of the present invention are those with an H.L.B range of from 7 to 17.
Depending on the nature of the compound to be formulated, suitable surface-active compounds are nonionic, cationic and/or anionic surfactants or a mixture of such surfactants, the surfactant or surfactant mixture having good emulsifying, dispersing and wetting capabilities. Preferred nonionic surfactants are polyethoxylated castor oil, polyadducts of polypropylene and polyethylene oxide, tributylphenol polyethoxylate, polyethylene glycol and octylphenol polyethoxylate. Fatty acid esters of polyoxyethylene sorbitan, e.g. polyoxyethylene sorbitan trioleate, are also suitable nonionic surfactants.
Preferred cationic surfactants for inclusion in the composition of the present invention include quaternary ammonium salts carrying, as N-substituent, at least one C8-C22 alkyi radical and, as a further substituent, unsubstituted or halogenated lower alkyi, benzyl or hydroxyl- lower alkyi radicals. The salts are preferably in the form of halide, methyl sulfate or ethyl sulfate. Examples of such cationic surfactants are stearyltrimethylammonium chloride and benzyl bis(2-chloroethyl)ethylammonium bromide.
Suitable anionic surfactants for use in the compositions include water-soluble soaps as well as water-soluble synthetic surface-active compounds, alkylarylsulfonates. Typical examples of alkylarylsulfonates are sodium, calcium or
triethanolammonium salt of dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid or a condensate of naphthalenesulfonic acid and formaldehyde. Corresponding phosphates, for example salts of phosphoric acid ester of an adduct of p-nonylphenol with 4 to 14 mol of ethylene oxide, or phospholipids, are also suitable.
The surfactant or surfactant mixture may be present in the composition in any suitable amount. Preferably, the surfactant is present in an amount in the range of from 5 to 40% by weight, more preferably from 5 to 35% by weight, still more preferably from 10 to 30% by weight. A surfactant concentration of from 20 to 30% by weight has been found to be particularly suitable in many embodiments.
Further components for inclusion in the composition are well known in the art and include, for example a stabilizer and a thickener. Such components are commercially available and their use will be recognized and understood by the person skilled in the art.
In a further aspect, the present invention provides a liquid concentrate comprising a benzoylphenyl urea and a C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether.
Other components that may be included in the liquid concentrate are as hereinbefore described. Details of the components of the liquid concentrate are as given hereinbefore.
In a further aspect, the present invention provides the use of a C2-C4 dialkylene glycol di-/mono- C-|-C4 alkyl ether, preferably the C2-C4 dialkylene glycol di-/mono- Ci-C4 alkyl ethers as hereinbefore recited, to reduce the eye irritation of insecticidally-active benzoylphenyl urea derivatives.
The compositions of the present invention may be prepared using techniques known in the art. A particularly preferred method of preparing the composition is as follows:
Each component is added according to the weight fraction required in the final composition. First, the solvent as required, and one or more C2-C4 dialkylene glycol di-/mono- C C4 alkyl ethers are charged to a suitable mixing vessel, for example a
blending tank. The resulting mixture is agitated. The one or more benzoylphenyl urea derivatives are added to the mixture and the agitation continues until the benzoylphenyl urea derivatives are dissolved completely in the solvent. An agitation time of about 30 minutes is typical. Thereafter, further components, such as an emulsifier, if present, are added and the mixture is further agitated to ensure homogeneity. A further agitation time of about 1 hour is typical.
In a further aspect, the present invention provides a method of reducing the eye irritation of insecticide liquid formulations comprising benzoylphenyl urea derivative, comprising adding a C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether, preferably those C2-C4 dialkylene glycol di-/mono- C C4 alkyl ethers hereinbefore recited, to the formulation in an amount sufficient to reduce the eye irritancy of the benzoylphenyl urea derivative.
Embodiments of the present invention will now be described, by way of example only.
EXAMPLES
In each of the following examples, a composition was prepared according to the following general methodology:
Charge every component based on the recipe of the composition into a vessel in the following manner. First, add the solvent and C2-C4 dialkylene glycol di-/mono-
C C4 alkyl ether to a blending tank; agitate the mixture; add one or more benzoylphenyl urea active ingredients to the resulting mixture in the blending tank; continue agitating for 30 minutes until all benzoylphenyl urea active ingredients are dissolved completely; add the emulsifier to the resulting mixture in the tank; continue agitating for one hour until the mixture is uniform; stop agitating; and discharge the resulting composition from the blending tank.
The potential of the formulation to cause eye irritation was determined according to the method described by N. P. Luepke: 'Hen's Egg Chorio Allantoic Membrane Test for Irritation Potential', Fd. Chem. Toxic. 23 (1985), pp 287-291 , (hereafter the ΉΕΤ-CAM Test'), which was modified according to the method of H. Spielmann (H. Spielmann: Methods in Molecular Biology 43 (1995) pp. 199-204, and H. Spielmann et al. ATLA 24 (1996), pp. 741 -858).
In the HET-CAM test the chorio allantoic membrane is treated with test sample. The chorio allantoic membrane is then observed for 5 minutes with regard to haemorrhage, coagulation and vascular lysis. In terms of the time of occurrence and the severity of the symptoms, the test samples were categorized as follows:
Cat 0: strongly irritant
Cat I: irritant
Cat II: moderately irritant Cat III: non-irritant The composition and the eye irritation behavior of compositions according to the present invention, prepared and tested as described above, are described in the following examples, in conjunction with comparative test results given in respective tables.
Example 1 The liquid formulation described in Table 1 was prepared containing the indicated
C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether and lufenuron as active ingredient, wherein the ratio of lufenuron and C2-C4 dialkylene glycol di-/mono- C1-C4 alkyl ether was approximately 1 : 13. Eye irritancy of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical
manner, but without any C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether as eye irritation reducer.
The formulation of Example 1 contained C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether in an amount of 65%wt. Table 1 describes the liquid formulation of Example 1 and the comparison formulation, Comparison A.
Table 1
Example 2
The liquid formulation described in Table 2 was prepared containing the indicated C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether and novaluron as active ingredient, wherein the ratio of novaluron and C2-C4 dialkylene glycol di-/mono- C1-C4 alkyl ether
was approximately 1 :6. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without a C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether as eye irritation reducer.
The formulation of Example 2 contained the indicated C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether in an amount of 60%wt. Table 2 describes the liquid formulation of Example 2 and the comparison formulation, Comparison B.
Table 2
Example 3
The liquid formulation described in Table 3 was prepared containing the indicated C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether and hexaflumuron as active
ingredient, wherein the ratio of hexaflumuron and C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether was approximately 1 :7.25. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C2-C4 dialkylene glycol di-/mono- Ci-C4 alkyl ether as eye irritancy reducer.
The formulation of Example 3 contained C2-C4 dialkylene glycol di-/mono- Ci-C4 alkyl ether in an amount of 58%wt. Table 3 describes the liquid formulation of Example 3 and the comparison formulation, Comparison C.
Table 3
Example 4
The liquid formulation described in Table 4 was prepared containing the indicated
C2-C4 dialkylene glycol di-/mono- C1-C4 alkyl ether and triflumuron as active ingredient, wherein the ratio of triflumuron and C2-C4 dialkylene glycol di-/mono- C1-C4 alkyl ether was approximately 1 : 12. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C2-C4 dialkylene glycol di-/mono- C1-C4 alkyl ether as eye irritation reducer.
The formulation of Example 4 contained C2-C4 dialkylene glycol di-/mono- C1-C4 alkyl ether in an amount of 60%wt. Table 4 describes the liquid formulation of Example 4 and the comparison formulation, Comparison D. Table 4
Example 5
The liquid formulation described in Table 5 was prepared containing the indicated
C2-C4 dialkylene glycol di-/mono- C1-C4 alkyl ether and diflubenzuron as active ingredient, wherein the ratio of diflubenzuron and C2-C4 dialkylene glycol di-/mono- C1-C4 alkyl ether was approximately 1 :6. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C2-C4 dialkylene glycol di-/mono- C -C4 alkyl ether eye irritation reducer.
The formulation of Example 5 contained the C2-C4 dialkylene glycol di-/mono- ( C4 alkyl ether in an amount of 60%wt. Table 5 describes the liquid formulation of Example 5 and the comparison formulation, Comparison E.
Table 5
The liquid formulation described in Table 6 was prepared containing the indicated C2-C4 dialkylene glycol di-/mono- C1-C4 alkyl ether and chlorfluazuron as active ingredient, wherein the ratio of chlorfluazuron and C2-C4 dialkylene glycol di-/mono- C1-C4 alkyl ether was approximately 1 :2. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C2-C4 dialkylene glycol di-/mono- ( C4 alkyl ether as eye irritation reducer.
The formulation of Example 6 contained the C2-C4 dialkylene glycol di-/mono- C1-C4 alkyl ether in an amount of 40%wt. Table 6 describes the liquid formulation of Example 6 and the comparison formulation, Comparison F.
Table 6
The liquid formulation described in Table 7 was prepared containing the indicated C2-C4 dialkylene glycol di-/mono- C1-C4 alkyl ether and flufenoxuron as the active ingreduent, wherein the ratio of flufenoxuron and the C2-C4 dialkylene glycol di-/mono- C1-C4 alkyl ether was approximately 1 : 1 .6. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C2-C4 dialkylene glycol di-/mono- ( C4 alkyl ether as eye irritation reducer.
The formulation of Example 7 contained the C2-C4 dialkylene glycol di-/mono- C1-C4 alkyl ether in an amount of 40%wt. Table 7 describes the liquid formulation of Example 7 and the comparison formulation, Comparison G.
Table 7
The liquid formulation described in Table 8 was prepared containing the indicated C2-C4 dialkylene glycol di-/mono- C1-C4 alkyl ether and noviflumuron as the active ingredient, wherein the ratio of noviflumuron and C2-C4 dialkylene glycol di-/mono- C1-C4 alkyl ether was approximately 1 : 12. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C2-C4 dialkylene glycol di-/mono- ( C4 alkyl ether as eye irritation reducer.
The formulation of Example 8 contained the C2-C4 dialkylene glycol di-/mono- C1-C4 alkyl ether in an amount of 60%wt. Table 8 describes the liquid formulation of Example 8 and the comparison formulation, Comparison H.
Table 8
The liquid formulation described in Table 9 was prepared containing the indicated C2-C4 dialkylene glycol di-/mono- C1-C4 alkyl ether and teflubenuron as the active ingredient, wherein the ratio of teflubenuron and the C2-C4 dialkylene glycol di-/mono- C1-C4 alkyl ether was approximately 1 : 15. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C2-C4 dialkylene glycol di-/mono- ( C4 alkyl ether as eye irritation reducer.
The formulation of Example 9 contained the C2-C4 dialkylene glycol di-/mono- C1-C4 alkyl ether in an amount of 60%wt. Table 9 describes the liquid formulation of Example 9 and the comparison formulation, Comparison I.
Table 9
EXAMPLE 9: teflubenuron EC (with : COMPARISON I: teflubenuron EC Remark eye irritation reducer) (without irritation reducer)
Component Composition Component Composition
teflubenuron tech 40kg( as ; teflubenuron tech 40kg ( as Active pure) pure) ingredient
Sodium 100kg Sodium 100kg Emulsifier dodecylphenylsulfonate dodecylphenylsulfonate
TWEEN 80 160kg TWEEN 80 160kg Emulsifier Sorbitan monooleate Sorbitan monooleate
ethoxylate ethoxylate
Gamma-butyrolactone 100kg Gamma-butyrolactone 700kg Solvent dipropylene glycol ethyl 600kg Eye ether irritation reducer
Total 1000kg Total 1000kg
Example 10
The liquid formulation described in Table 10 was prepared containing the indicated C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether and a combination of novaluron and lufenuron as active ingredients, wherein the ratio of novaluron plus lufenuron and the C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether was approximately 1 :6. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether as eye irritation reducer.
The formulation of Example 10 contained the C2-C4 dialkylene glycol di-/mono-
Ci-C4 alkyl ether in an amount of 60%wt. Table 10 describes the liquid formulation of Example 10 and the comparison formulation, Comparison J.
Table 10
The liquid formulation described in Table 11 was prepared containing the indicated C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether and a combination of triflumuron and hexaflumuron as active ingredients, wherein the ratio of triflumuron plus hexaflumuron and the C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether was approximately 1 :2.5. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether as eye irritation reducer.
The formulation of Example 11 contained the C2-C4 dialkylene glycol di-/mono-
Ci-C4 alkyl ether in an amount of 50%wt. Table 11 describes the liquid formulation of Example 11 and the comparison formulation, Comparison K.
Table 11
The liquid formulation described in Table 12 was prepared containing the indicated C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether and a combination of diflubenzuron and chlorfluazuron as active ingredients, wherein the ratio of diflubenzuron plus chlorfluazuron and the C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether was approximately 1 :2.75. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether as eye irritation reducer.
The formulation of Example 12 contained the C2-C4 dialkylene glycol di-/mono-
Ci-C4 alkyl ether in an amount of 55%wt. Table 1 describes the liquid formulation of Example 12 and the comparison formulation, Comparison L.
Table 12
The liquid formulation described in Table 13 was prepared containing the indicated C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether and a combination of flufenoxuron and noviflumuron as active ingredients, wherein the ratio of flufenoxuron plus noviflumuron and the C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether was approximately 1 : 1 .4. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether as eye irritation reducer.
The formulation of Example 13 contained the C2-C4 dialkylene glycol di-/mono-
Ci-C4 alkyl ether in an amount of 35%wt. Table 13 describes the liquid formulation of Example 1 and the comparison formulation, Comparison M.
Table 13
The liquid formulation described in Table 1 was prepared containing the indicated C2-C4 dialkylene glycol di-/mono- C1-C4 alkyl ether and a combination of noviflumuron and teflubenzuron as active ingredients, wherein the ratio of noviflumuron plus teflubenzuron and the C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether was approximately 1 : 1 .3. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether as eye irritation reducer.
The formulation of Example 14 contained the C2-C4 dialkylene glycol di-/mono-
Ci-C4 alkyl ether in an amount of 40%wt. Table 14 describes the liquid formulation of Example 14 and the comparison formulation, Comparison N.
Table 14
The liquid formulation described in Table 15 was prepared containing the indicated C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether and a combination of novaluron and hexaflumuron as active ingredients, wherein the ratio of novaluron plus hexaflumuron and C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether was approximately 1 :6. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether as eye irritation reducer.
The formulation of Example 15 contained the C2-C4 dialkylene glycol di-/mono-
Ci-C4 alkyl ether in an amount of 65%wt. Table 15 describes the liquid formulation of Example 15 and the comparison formulation, Comparison O.
Table 15
EXAMPLE 15: COMPARISON O: Remark novaluron+hexaflumuron EC (with eye I novaluron+hexaflumuron EC (without
irritation reducer) I irritation reducer)
Component Composition I Component Composition
novaluron tech 50kg( as 1 novaluron tech 50kg ( as Active pure) pure) ingredient
Hexaflumuron tech 50kg(as 1 Hexaflumuron tech 50kg(as Active pure) pure) ingredient
Sodium 100kg f Sodium 100kg Emulsifier dodecylphenylsulfonate f dodecylphenylsulfonate
TWEEN 80 100kg TWEEN 80 100kg Emulsifier
Sorbitan monooleate 1 Sorbitan monooleate
ethoxylate I ethoxylate
Gamma-butyrolactone 100kg I Gamma-butyrolactone 700kg Solvent dipropylene glycol 600kg Eye propyl ether irritation reducer
Total 1000kg I Total 1000kg
Example 16
The liquid formulation described in Table 16 was prepared containing the indicated C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether and a combination of lufenuron and triflumuron as active ingredients, wherein the ratio of lufenuron plus triflumuron and C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether was approximately 1 :2.9. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether as eye irritation reducer.
The formulation of Example 16 contained the C2-C4 dialkylene glycol di-/mono- Ci-C4 alkyl ether in an amount of 52%wt. Table 16 describes the liquid formulation of Example 16 and the comparison formulation, Comparison P.
Table 16
The liquid formulation described in Table 17 was prepared containing the indicated C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether and a combination of lufenuron and diflubenzuron as active ingredients, wherein the ratio of lufenuron plus diflubenzuron and C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether was approximately 1 : 1 .8. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether as eye irritation reducer.
The formulation of Example 17 contained the C2-C4 dialkylene glycol di-/mono-
Ci-C4 alkyl ether in an amount of 45%wt. Table 17 describes the liquid formulation of Example 17 and the comparison formulation, Comparison Q.
Table 17
The liquid formulation described in Table 18 was prepared containing the indicated C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether and a combination of lufenuron and chlorfluazuron as active ingredients, wherein the ratio of lufenuron plus chlorfluazuron and C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether was approximately 1 : 1 .4. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether as eye irritation reducer.
The formulation of Example 18 contained the C2-C4 dialkylene glycol di-/mono-
Ci-C4 alkyl ether in an amount of 65%wt. Table 18 describes the liquid formulation of Example 18 and the comparison formulation, Comparison R.
Table 18
The liquid formulation described in Table 19 was prepared containing the indicated C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether and a combination of lufenuron and flufenoxuron as active ingredients, wherein the ratio of lufenuron plus flufenoxuron and C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether was approximately 1 :7. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether as eye irritation reducer.
The formulation of Example 19 contained the C2-C4 dialkylene glycol di-/mono-
Ci-C4 alkyl ether in an amount of 70%wt. Table 19 describes the liquid formulation of Example 19 and the comparison formulation, Comparison S.
Table 19
The liquid formulation described in Table 20 was prepared containing the indicated C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether and a combination of lufenuron and noviflumuron as active ingredients, wherein the ratio of lufenuron plus noviflumuron and C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether was approximately 1 : 1. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether as eye irritation reducer.
The formulation of Example 20 contained the C2-C4 dialkylene glycol di-/mono-
Ci-C4 alkyl ether in an amount of 35%wt. Table 20 describes the liquid formulation of Example 20 and the comparison formulation, Comparison T.
Table 20
The liquid formulation described in Table 21 was prepared containing the indicated C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether and a combination of lufenuron and teflubenzuron as active ingredients, wherein the ratio of lufenuron plus teflubenzuron and C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether was approximately 1 :6. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether as eye irritation reducer.
The formulation of Example 1 contained the C2-C4 dialkylene glycol di-/mono-
Ci-C4 alkyl ether in an amount of 60%wt. Table 21 describes the liquid formulation of Example 21 and the comparison formulation, Comparison U.
Table 21
The liquid formulation described in Table 22 was prepared containing the indicated C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether and a combination of triflumuron and teflubenzuron as active ingredient, wherein the ratio of triflumuron plus teflubenzuron and the C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether was approximately 1 :2. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether as eye irritation reducer.
The formulation of Example 22 contained the C2-C4 dialkylene glycol di-/mono-
Ci-C4 alkyl ether in an amount of 40%wt. Table 22 describes the liquid formulation of Example 22 and the comparison formulation, Comparison V.
Table 22
The liquid formulation described in Table 23 was prepared containing the indicated C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether and a combination of triflumuron and noviflumuron as active ingredients, wherein the ratio of triflumuron plus noviflumuron and C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether was approximately 1 :3.3. Eye irritation of this formulation was compared with a second liquid formulation, which was prepared from identical components in an identical manner, but without any C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether as eye irritation reducer.
The formulation of Example 23 contained the C2-C4 dialkylene glycol di-/mono-
Ci-C4 alkyl ether in an amount of 50%wt. Table 23 describes the liquid formulation of Example 23 and the comparison formulation, Comparison 23.
Table 23
The potential of the formulation to cause eye irritation was determined according to the method described by N. P. Luepke: Hen's Egg Chorio Allantoic Membrane Test for Irritation Potential, Fd. Chem. Toxic. 23 (1985), pp 287-291 , (HET-CAM Test) which was modified according to the method of H. Spielmann (H. Spielmann: Methods in Molecular Biology 43 (1995) pp. 199-204, and H. Spielmann et al. ATLA 24 (1996), pp. 741-858).
In the HET-CAM test the chorio allantoic membrane is treated with test sample. The chorio allantoic membrane is then observed for 5 minutes with regard to haemorrhage, coagulation and vascular lysis. In terms of the time of occurrence and the severity of the symptoms, the test samples are categorized as follows:
Cat 0: strongly irritant
Cat I: irritant
Cat II: moderately irritant
Cat III: non-irritant
Examples Results
Example 1 Cat III
Comparison A Cat O
Example 2 Cat III
Comparison B Cat O
Example 3 Cat III
Comparison C Cat O
Example 4 Cat II
Comparison D Cat O
Example 5 Cat III
Comparison E Cat O
Example 6 Cat II
Comparison F Cat O
Example 7 Cat II
Comparison G Cat O
Example 8 Cat III
Comparison H Cat O
Example 9 Cat III
Comparison I Cat O
Example 10 Cat III
Comparison J Cat O
Example 1 1 Cat III
Comparison K Cat O
Example 12 Cat III
Comparison L Cat O
Example 13 Cat II
Comparison M Cat O
Example 14 Cat II
Comparison N Cat O
Example 15 Cat III
Comparison 0 Cat O
Example 16 Cat III
Comparison P Cat O
Example 17 Cat II
Comparison Q Cat O
Example 18 Cat II
Comparison R Cat O
Example 19 Cat III
Comparison S Cat O
Example 20 Cat II
Comparison T Cat O
Example 21 Cat III
Comparison U Cat O
Example 22 Cat II
Comparison V Cat O
Example 23 Cat III
Comparison W Cat O
From the experimental data set out above, it can be seen that C2-C4 dialkylene glycol di-/mono- C1-C4 alkyl ethers above exhibit significant performance in reducing the eye irritation of the insecticidally active benzoylphenyl urea derivatives.
Claims
1 . An agrochemical composition comprising a C2-C4 dialkylene glycol di-/mono- Ci-C4 alkyl ether, at least one benzoylphenyl urea active ingredient and optionally at least one member selected from the group consisting of a surface-active agent, an organic polar solvent and a low temperature stabilizer.
2. The composition according to claim 1 , wherein the ratio of benzoylphenyl urea active ingredient and C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether is from 1 :1 to 1 :30, preferably from 1 :3 to 1 : 15.
3. The composition according to any preceding claim, wherein two or more C2-C4 dialkylene glycol di-/mono- C C4 alkyl ethers are present.
4. The composition according to any preceding claim, wherein two or more benzoylphenyl urea active ingredients are present.
5. The composition according to any preceding claim, wherein the C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether is one or more selected from the group consisting of diethylene glycol dimethyl ether, diethylene glycol methyl ether, dipropylene glycol dimethyl ether, dipropylene glycol methyl ether, dibutylene glycol dimethyl ether, dibutylene glycol methyl ether, diethylene glycol diethyl ether, diethylene glycol ethyl ether, dipropylene glycol diethyl ether, dipropylene glycol ethyl ether, dibutylene glycol diethyl ether, dibutylene glycol ethyl ether, diethylene glycol dipropyl ether, diethylene glycol propyl ether, dipropylene glycol dipropyl ether, dipropylene glycol propyl ether, dibutylene glycol dipropyl ether, dibutylene glycol propyl ether, diethylene glycol dibutyl ether, diethylene glycol butyl ether, dipropylene glycol dibutyl ether, dipropylene glycol butyl ether, dibutylene glycol dibutyl ether, dibutylene glycol butyl ether and mixtures thereof.
6. The composition according to any preceding claim, wherein the C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether is present in an amount of from 5% to 80% by weight.
7. The composition according to any preceding claim, wherein the benzoylphenyl urea derivative is one or more selected from the group consisting of novaluron, lufenuron, hexaflumuron .triflumuron, diflubenzuron, chlorfluazuron, flufenoxuron, noviflumuron and teflubenzuron and mixtures thereof.
8. The composition according to any preceding claim, wherein the benzoylphenyl urea is present in an amount of from 2 to 50% by weight.
9. The composition according to any preceding claim, further comprising a polar solvent.
10. The composition according to claim 9, wherein the polar solvent is one or more selected from the group consisting of benzyl alcohol, an alkyl pyrrolidone such as N-metylprrolidone, N-octylpyrrolidone, or a lactone such as γ-butyrolactone.
1 1. The composition according to either of claims 9 or 10, wherein the polar solvent is present in an amount of from 10 to 90% by weight.
12. The composition according to any preceding claim, further comprising an emulsifier.
13. The composition according to claim 12, wherein the emulsifier is present in an amount of from 5 to 40% by weight.
14. The composition according to any preceding, being a liquid concentrate, in particular an emulsion concentrate (EC) formulation.
15. A use of a C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether to reduce eye irritation of an insecticidal benzoylphenyl urea derivative.
16. The use according to claim 15, wherein the C2-C4 dialkylene glycol di-/mono- Ci-C4 alkyl ether is combined with the benzoylphenyl urea derivative in an insecticidal composition.
17. A method of reducing eye irritation of insecticidal liquid formulations comprising a benzoylphenyl urea derivative, the method comprising including a C2-C4 dialkylene glycol di-/mono- C C4 alkyl ether in the formulation in an amount sufficient to reduce eye irritation of the benzoylphenyl urea derivative.
18. A method of treating pest at a locus, comprising applying to the locus a composition as claimed in any of claims 1 to 14.
19. The method according to claim 18, wherein the composition is an emulsion concentrate, the composition being dispersed in water before application to the locus.
20. The use of a composition according to any of claims 1 to 14 in the control of pests.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CR20180464A CR20180464A (en) | 2010-06-17 | 2011-05-25 | PESTICIDE COMPOSITION (Divisional 2012-0639) |
| CN201180029519.7A CN103037689B (en) | 2010-06-17 | 2011-05-25 | Pesticidal Composition |
| AP2013006676A AP3460A (en) | 2010-06-17 | 2011-05-25 | Pesticidal composition |
| MYPI2012005441A MY165577A (en) | 2010-06-17 | 2011-05-25 | Pesticidal composition |
| GB1300623.4A GB2495659B (en) | 2010-06-17 | 2011-05-25 | Pesticidal composition |
| UAA201300490A UA106668C2 (en) | 2010-06-17 | 2011-05-25 | PESTICIDE COMPOSITION |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BRPI1002174-4 | 2010-06-17 | ||
| BRPI1002174-4A BRPI1002174A2 (en) | 2010-06-17 | 2010-06-17 | AGROCHEMICAL COMPOSITION, USE OF A C2-C4 DIALKYLENE GLYCOL DI- / MONO-C1-C4 Ether AQUIL, METHOD TO REDUCE EYE IRRITATION OF INSETICID FORMULATIONS, LOCAL PEST TREATMENT METHOD AND |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2011157101A1 true WO2011157101A1 (en) | 2011-12-22 |
Family
ID=45347659
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/CN2011/074622 WO2011157101A1 (en) | 2010-06-17 | 2011-05-25 | Pesticidal composition |
Country Status (13)
| Country | Link |
|---|---|
| CN (1) | CN103037689B (en) |
| AP (1) | AP3460A (en) |
| AR (1) | AR081951A1 (en) |
| BR (1) | BRPI1002174A2 (en) |
| CL (1) | CL2012003563A1 (en) |
| CO (1) | CO6650418A2 (en) |
| CR (2) | CR20180464A (en) |
| GB (1) | GB2495659B (en) |
| MY (1) | MY165577A (en) |
| PE (1) | PE20131029A1 (en) |
| TW (1) | TWI409032B (en) |
| UA (1) | UA106668C2 (en) |
| WO (1) | WO2011157101A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016124610A1 (en) * | 2015-02-03 | 2016-08-11 | Bimeda Finance S.A.R.L. | A formulation for treatment of blowfly strike |
| US11629105B2 (en) | 2016-06-02 | 2023-04-18 | Croda International Plc | Plant treatment composition |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000030449A1 (en) * | 1998-11-19 | 2000-06-02 | Pfizer Limited | Antiparasitic formulations |
| US6121199A (en) * | 1990-08-09 | 2000-09-19 | Monsanto Company | Herbicidal compositions of polyoxyalkylene alkylamine surfactants having reduced eye irritation |
| WO2011044475A1 (en) * | 2009-10-08 | 2011-04-14 | Sergeant's Pet Care Products, Inc. | Liquid pest control formulation |
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|---|---|---|---|---|
| NZ505779A (en) * | 2000-07-14 | 2003-06-30 | Akzo Nobel Nv | Pesticidal composition containing insect growth regulating (IGR) insecticide in an aromatic hydrocarbon and/or pyrrolidone and/or propylene glycol monoalkyl ether solvent system |
| WO2005053746A1 (en) * | 2003-12-04 | 2005-06-16 | Jurox Pty Ltd | Improved parasiticide composition |
| JP2006056810A (en) * | 2004-08-19 | 2006-03-02 | Shinto Fine Co Ltd | Harmful insect-controlling composition and harmful insect-controlling method |
| AU2005100403B4 (en) * | 2005-05-13 | 2005-09-01 | Jurox Pty Ltd | Parasiticide Composition |
| AR058921A1 (en) * | 2006-01-05 | 2008-03-05 | Basf Ag | MIXTURE OF SOLVENTS TO PREPARE A FORMULATION OF HYDROSOLUBLE LIQUID CONCENTRATE OF ORGANIC PESTICIDE COMPOUNDS |
| KR101424829B1 (en) * | 2006-03-24 | 2014-08-01 | 바스프 에스이 | Agrochemical formulations |
| CN101697733B (en) * | 2009-09-30 | 2014-08-13 | 深圳诺普信农化股份有限公司 | Lufenuron-containing aqueous emulsion and preparation method thereof |
-
2010
- 2010-06-17 BR BRPI1002174-4A patent/BRPI1002174A2/en not_active Application Discontinuation
-
2011
- 2011-05-25 PE PE2012002440A patent/PE20131029A1/en not_active Application Discontinuation
- 2011-05-25 MY MYPI2012005441A patent/MY165577A/en unknown
- 2011-05-25 WO PCT/CN2011/074622 patent/WO2011157101A1/en active Application Filing
- 2011-05-25 GB GB1300623.4A patent/GB2495659B/en not_active Expired - Fee Related
- 2011-05-25 CN CN201180029519.7A patent/CN103037689B/en not_active Expired - Fee Related
- 2011-05-25 UA UAA201300490A patent/UA106668C2/en unknown
- 2011-05-25 AP AP2013006676A patent/AP3460A/en active
- 2011-05-25 CR CR20180464A patent/CR20180464A/en unknown
- 2011-06-16 AR ARP110102096A patent/AR081951A1/en not_active Application Discontinuation
- 2011-06-16 TW TW100121067A patent/TWI409032B/en active
-
2012
- 2012-12-17 CO CO12228123A patent/CO6650418A2/en not_active Application Discontinuation
- 2012-12-17 CL CL2012003563A patent/CL2012003563A1/en unknown
- 2012-12-17 CR CR20120639A patent/CR20120639A/en unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6121199A (en) * | 1990-08-09 | 2000-09-19 | Monsanto Company | Herbicidal compositions of polyoxyalkylene alkylamine surfactants having reduced eye irritation |
| WO2000030449A1 (en) * | 1998-11-19 | 2000-06-02 | Pfizer Limited | Antiparasitic formulations |
| WO2011044475A1 (en) * | 2009-10-08 | 2011-04-14 | Sergeant's Pet Care Products, Inc. | Liquid pest control formulation |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016124610A1 (en) * | 2015-02-03 | 2016-08-11 | Bimeda Finance S.A.R.L. | A formulation for treatment of blowfly strike |
| GB2551451A (en) * | 2015-02-03 | 2017-12-20 | Bimeda Finance S A R L | A formulation for treatment of blowfly strike |
| GB2551451B (en) * | 2015-02-03 | 2020-05-27 | Bimeda Finance S A R L | A formulation for treatment of blowfly strike |
| GB2580572A (en) * | 2015-02-03 | 2020-07-22 | Bimeda Finance S A R L | A formulation for treatment of blowfly strike |
| AU2019283896B2 (en) * | 2015-02-03 | 2021-04-01 | Bimeda Finance S.A.R.L. | A formulation for treatment of blowfly strike |
| US11629105B2 (en) | 2016-06-02 | 2023-04-18 | Croda International Plc | Plant treatment composition |
Also Published As
| Publication number | Publication date |
|---|---|
| CR20180464A (en) | 2019-01-14 |
| CN103037689B (en) | 2014-10-08 |
| TW201200022A (en) | 2012-01-01 |
| UA106668C2 (en) | 2014-09-25 |
| PE20131029A1 (en) | 2013-09-18 |
| AP2013006676A0 (en) | 2013-01-31 |
| MY165577A (en) | 2018-04-05 |
| TWI409032B (en) | 2013-09-21 |
| GB2495659A (en) | 2013-04-17 |
| CR20120639A (en) | 2013-04-08 |
| GB2495659B (en) | 2017-10-04 |
| CN103037689A (en) | 2013-04-10 |
| BRPI1002174A2 (en) | 2012-03-13 |
| AP3460A (en) | 2015-11-30 |
| GB201300623D0 (en) | 2013-02-27 |
| CO6650418A2 (en) | 2013-04-15 |
| CL2012003563A1 (en) | 2013-12-06 |
| AR081951A1 (en) | 2012-10-31 |
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