GB2571647A - An agrochemical composition, a method of preparing the same and the use thereof - Google Patents
An agrochemical composition, a method of preparing the same and the use thereof Download PDFInfo
- Publication number
- GB2571647A GB2571647A GB1906116.7A GB201906116A GB2571647A GB 2571647 A GB2571647 A GB 2571647A GB 201906116 A GB201906116 A GB 201906116A GB 2571647 A GB2571647 A GB 2571647A
- Authority
- GB
- United Kingdom
- Prior art keywords
- glycol dibenzoate
- emulsifier
- dipropylene
- diethylene glycol
- composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 47
- 239000012872 agrochemical composition Substances 0.000 title claims abstract description 12
- NXQMCAOPTPLPRL-UHFFFAOYSA-N 2-(2-benzoyloxyethoxy)ethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCOCCOC(=O)C1=CC=CC=C1 NXQMCAOPTPLPRL-UHFFFAOYSA-N 0.000 claims abstract description 180
- 239000000203 mixture Substances 0.000 claims abstract description 164
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 113
- PZTAGFCBNDBBFZ-UHFFFAOYSA-N tert-butyl 2-(hydroxymethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1CO PZTAGFCBNDBBFZ-UHFFFAOYSA-N 0.000 claims abstract description 111
- 239000004480 active ingredient Substances 0.000 claims abstract description 69
- 206010015946 Eye irritation Diseases 0.000 claims abstract description 46
- 231100000013 eye irritation Toxicity 0.000 claims abstract description 46
- 238000009472 formulation Methods 0.000 claims abstract description 37
- NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000005874 Bifenthrin Substances 0.000 claims abstract description 24
- 239000005927 Pyriproxyfen Substances 0.000 claims abstract description 24
- OMFRMAHOUUJSGP-IRHGGOMRSA-N bifenthrin Chemical compound C1=CC=C(C=2C=CC=CC=2)C(C)=C1COC(=O)[C@@H]1[C@H](\C=C(/Cl)C(F)(F)F)C1(C)C OMFRMAHOUUJSGP-IRHGGOMRSA-N 0.000 claims abstract description 24
- KIEDNEWSYUYDSN-UHFFFAOYSA-N clomazone Chemical compound O=C1C(C)(C)CON1CC1=CC=CC=C1Cl KIEDNEWSYUYDSN-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000005660 Abamectin Substances 0.000 claims abstract description 17
- 239000005499 Clomazone Substances 0.000 claims abstract description 17
- 235000014666 liquid concentrate Nutrition 0.000 claims abstract description 15
- 239000005497 Clethodim Substances 0.000 claims abstract description 13
- IBSREHMXUMOFBB-JFUDTMANSA-N 5u8924t11h Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C(C)C)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 IBSREHMXUMOFBB-JFUDTMANSA-N 0.000 claims abstract description 11
- 229950008167 abamectin Drugs 0.000 claims abstract description 11
- 239000007788 liquid Substances 0.000 claims abstract description 3
- 239000004495 emulsifiable concentrate Substances 0.000 claims description 34
- -1 sorbitan fatty acid ester Chemical class 0.000 claims description 28
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 19
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 14
- 239000011575 calcium Substances 0.000 claims description 14
- 229910052791 calcium Inorganic materials 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 13
- 125000002091 cationic group Chemical group 0.000 claims description 13
- 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 13
- 239000005912 Lufenuron Substances 0.000 claims description 12
- SILSDTWXNBZOGF-KUZBFYBWSA-N chembl111058 Chemical compound CCSC(C)CC1CC(O)=C(\C(CC)=N\OC\C=C\Cl)C(=O)C1 SILSDTWXNBZOGF-KUZBFYBWSA-N 0.000 claims description 12
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 12
- 239000000194 fatty acid Substances 0.000 claims description 12
- 229930195729 fatty acid Natural products 0.000 claims description 12
- 229960000521 lufenuron Drugs 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000012875 nonionic emulsifier Substances 0.000 claims description 10
- 239000004359 castor oil Substances 0.000 claims description 7
- 235000019438 castor oil Nutrition 0.000 claims description 7
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 7
- 239000002728 pyrethroid Substances 0.000 claims description 7
- ZPFAVCIQZKRBGF-UHFFFAOYSA-N 1,3,2-dioxathiolane 2,2-dioxide Chemical compound O=S1(=O)OCCO1 ZPFAVCIQZKRBGF-UHFFFAOYSA-N 0.000 claims description 6
- 229920002101 Chitin Polymers 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 claims description 6
- RRZXIRBKKLTSOM-XPNPUAGNSA-N avermectin B1a Chemical compound C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 RRZXIRBKKLTSOM-XPNPUAGNSA-N 0.000 claims description 6
- PLUHAVSIMCXBEX-UHFFFAOYSA-N azane;dodecyl benzenesulfonate Chemical compound N.CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 PLUHAVSIMCXBEX-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 150000004665 fatty acids Chemical class 0.000 claims description 6
- 239000003112 inhibitor Substances 0.000 claims description 6
- 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 description 6
- 150000002923 oximes Chemical class 0.000 claims description 6
- 238000003786 synthesis reaction Methods 0.000 claims description 6
- 239000003760 tallow Substances 0.000 claims description 6
- 235000008504 concentrate Nutrition 0.000 abstract description 19
- 239000012141 concentrate Substances 0.000 abstract description 19
- 239000000839 emulsion Substances 0.000 abstract description 16
- SILSDTWXNBZOGF-JWGBMQLESA-N clethodim Chemical compound CCSC(C)CC1CC(O)=C(C(CC)=NOC\C=C\Cl)C(=O)C1 SILSDTWXNBZOGF-JWGBMQLESA-N 0.000 abstract 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 33
- 239000002904 solvent Substances 0.000 description 27
- HCWYXKWQOMTBKY-UHFFFAOYSA-N calcium;dodecyl benzenesulfonate Chemical compound [Ca].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 HCWYXKWQOMTBKY-UHFFFAOYSA-N 0.000 description 17
- 239000003638 chemical reducing agent Substances 0.000 description 13
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical group OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 11
- 239000002085 irritant Substances 0.000 description 11
- 231100000021 irritant Toxicity 0.000 description 11
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 9
- 229920000136 polysorbate Polymers 0.000 description 9
- 239000001593 sorbitan monooleate Substances 0.000 description 9
- 229940035049 sorbitan monooleate Drugs 0.000 description 9
- 235000011069 sorbitan monooleate Nutrition 0.000 description 9
- 231100000419 toxicity Toxicity 0.000 description 8
- 230000001988 toxicity Effects 0.000 description 8
- 238000002156 mixing Methods 0.000 description 6
- 125000000129 anionic group Chemical group 0.000 description 5
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 4
- LXODQLXKQIJVNK-UHFFFAOYSA-N 2-(2-benzoyloxypropoxy)propyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC(C)COC(C)COC(=O)C1=CC=CC=C1 LXODQLXKQIJVNK-UHFFFAOYSA-N 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- 235000019445 benzyl alcohol Nutrition 0.000 description 4
- 210000003711 chorioallantoic membrane Anatomy 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 241000607479 Yersinia pestis Species 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZXQYGBMAQZUVMI-RDDWSQKMSA-N (1S)-cis-(alphaR)-cyhalothrin Chemical compound CC1(C)[C@H](\C=C(/Cl)C(F)(F)F)[C@@H]1C(=O)O[C@@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-RDDWSQKMSA-N 0.000 description 2
- BTYQXKURSPAXLT-UHFFFAOYSA-N 2,6-dichloro-n-[(4-chlorophenyl)carbamoyl]benzamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC(=O)C1=C(Cl)C=CC=C1Cl BTYQXKURSPAXLT-UHFFFAOYSA-N 0.000 description 2
- YPSCQJTUAKNUNF-UHFFFAOYSA-N 2-chloro-n-[(4-chlorophenyl)carbamoyl]benzamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl YPSCQJTUAKNUNF-UHFFFAOYSA-N 0.000 description 2
- CJRJTCMSQLEPFQ-UHFFFAOYSA-N 6-cat Chemical compound ClC1=CC=C2CC(N)CCC2=C1 CJRJTCMSQLEPFQ-UHFFFAOYSA-N 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- PNCNFDRSHBFIDM-WOJGMQOQSA-N chembl111617 Chemical compound C=CCO\N=C(/CCC)C1=C(O)C(C(=O)OC)C(C)(C)CC1=O PNCNFDRSHBFIDM-WOJGMQOQSA-N 0.000 description 2
- 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 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 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 description 2
- 239000002917 insecticide Substances 0.000 description 2
- YNKFZRGTXAPYFD-UHFFFAOYSA-N n-[[2-chloro-3,5-bis(trifluoromethyl)phenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1Cl YNKFZRGTXAPYFD-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 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 description 2
- 239000003495 polar organic solvent Substances 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 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 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 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 description 2
- SPVZAYWHHVLPBN-WREUKLMHSA-N (1r,3r)-3-[(z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)[C@@H](\C=C(/Cl)C(F)(F)F)[C@H]1C(O)=O SPVZAYWHHVLPBN-WREUKLMHSA-N 0.000 description 1
- PCKNFPQPGUWFHO-SXBRIOAWSA-N (Z)-flucycloxuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC(C=C1)=CC=C1CO\N=C(C=1C=CC(Cl)=CC=1)\C1CC1 PCKNFPQPGUWFHO-SXBRIOAWSA-N 0.000 description 1
- JTHMHWAHAKLCKT-UHFFFAOYSA-N 2,6-difluoro-n-[[4-(trifluoromethyl)phenyl]carbamoyl]benzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(C(F)(F)F)C=C1 JTHMHWAHAKLCKT-UHFFFAOYSA-N 0.000 description 1
- YXBDMGSFNUJTBR-NFSGWXFISA-N 2-[(E)-N-[(E)-3-chloroprop-2-enoxy]-C-propylcarbonimidoyl]-5-(2-ethylsulfanylpropyl)-3-hydroxycyclohex-2-en-1-one Chemical compound Cl/C=C/CO\N=C(/CCC)C1=C(O)CC(CC(C)SCC)CC1=O YXBDMGSFNUJTBR-NFSGWXFISA-N 0.000 description 1
- KRQUFUKTQHISJB-YYADALCUSA-N 2-[(E)-N-[2-(4-chlorophenoxy)propoxy]-C-propylcarbonimidoyl]-3-hydroxy-5-(thian-3-yl)cyclohex-2-en-1-one Chemical compound CCC\C(=N/OCC(C)OC1=CC=C(Cl)C=C1)C1=C(O)CC(CC1=O)C1CCCSC1 KRQUFUKTQHISJB-YYADALCUSA-N 0.000 description 1
- AZSNMRSAGSSBNP-UHFFFAOYSA-N 22,23-dihydroavermectin B1a Natural products C1CC(C)C(C(C)CC)OC21OC(CC=C(C)C(OC1OC(C)C(OC3OC(C)C(O)C(OC)C3)C(OC)C1)C(C)C=CC=C1C3(C(C(=O)O4)C=C(C)C(O)C3OC1)O)CC4C2 AZSNMRSAGSSBNP-UHFFFAOYSA-N 0.000 description 1
- SPVZAYWHHVLPBN-HYXAFXHYSA-N 3-[(z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)C(\C=C(/Cl)C(F)(F)F)C1C(O)=O SPVZAYWHHVLPBN-HYXAFXHYSA-N 0.000 description 1
- ZOGDSYNXUXQGHF-UHFFFAOYSA-N 5-(3-butanoyl-2,4,6-trimethylphenyl)-2-(N-ethoxy-C-ethylcarbonimidoyl)-3-hydroxycyclohex-2-en-1-one Chemical compound CCCC(=O)C1=C(C)C=C(C)C(C2CC(=O)C(C(CC)=NOCC)=C(O)C2)=C1C ZOGDSYNXUXQGHF-UHFFFAOYSA-N 0.000 description 1
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 1
- SPBDXSGPUHCETR-JFUDTMANSA-N 8883yp2r6d Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O[C@@H]([C@@H](C)CC4)C(C)C)O3)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1C[C@H](C)[C@@H]([C@@H](C)CC)O[C@@]21O[C@H](C\C=C(C)\[C@@H](O[C@@H]1O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C1)[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 SPBDXSGPUHCETR-JFUDTMANSA-N 0.000 description 1
- 241000532370 Atla Species 0.000 description 1
- ZOGDSYNXUXQGHF-XIEYBQDHSA-N Butroxydim Chemical compound CCCC(=O)C1=C(C)C=C(C)C(C2CC(=O)C(\C(CC)=N\OCC)=C(O)C2)=C1C ZOGDSYNXUXQGHF-XIEYBQDHSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000005501 Cycloxydim Substances 0.000 description 1
- 239000005946 Cypermethrin Substances 0.000 description 1
- 239000005892 Deltamethrin Substances 0.000 description 1
- 239000005893 Diflubenzuron Substances 0.000 description 1
- 239000005894 Emamectin Substances 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
- 208000032843 Hemorrhage Diseases 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- WPPOGHDFAVQKLN-UHFFFAOYSA-N N-Octyl-2-pyrrolidone Chemical compound CCCCCCCCN1CCCC1=O WPPOGHDFAVQKLN-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000005599 Profoxydim Substances 0.000 description 1
- CSPPKDPQLUUTND-NBVRZTHBSA-N Sethoxydim Chemical compound CCO\N=C(/CCC)C1=C(O)CC(CC(C)SCC)CC1=O CSPPKDPQLUUTND-NBVRZTHBSA-N 0.000 description 1
- 239000005938 Teflubenzuron Substances 0.000 description 1
- IOYNQIMAUDJVEI-BMVIKAAMSA-N Tepraloxydim Chemical compound C1C(=O)C(C(=N/OC\C=C\Cl)/CC)=C(O)CC1C1CCOCC1 IOYNQIMAUDJVEI-BMVIKAAMSA-N 0.000 description 1
- 239000005624 Tralkoxydim Substances 0.000 description 1
- 239000005942 Triflumuron Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 239000012874 anionic emulsifier Substances 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- GGWHBJGBERXSLL-NBVRZTHBSA-N chembl113137 Chemical compound C1C(=O)C(C(=N/OCC)/CCC)=C(O)CC1C1CSCCC1 GGWHBJGBERXSLL-NBVRZTHBSA-N 0.000 description 1
- DQFPEYARZIQXRM-UHFFFAOYSA-N chembl2355904 Chemical compound C1C(=O)C(C(CC)=NOCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-UHFFFAOYSA-N 0.000 description 1
- CSPPKDPQLUUTND-UHFFFAOYSA-N chembl3186232 Chemical compound CCON=C(CCC)C1=C(O)CC(CC(C)SCC)CC1=O CSPPKDPQLUUTND-UHFFFAOYSA-N 0.000 description 1
- MDIQXIJPQWLFSD-NJGYIYPDSA-N cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(O)=O MDIQXIJPQWLFSD-NJGYIYPDSA-N 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- GGWHBJGBERXSLL-UHFFFAOYSA-N cycloxydim Chemical compound C1C(=O)C(C(=NOCC)CCC)=C(O)CC1C1CSCCC1 GGWHBJGBERXSLL-UHFFFAOYSA-N 0.000 description 1
- ZXQYGBMAQZUVMI-UNOMPAQXSA-N cyhalothrin Chemical compound CC1(C)C(\C=C(/Cl)C(F)(F)F)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-UNOMPAQXSA-N 0.000 description 1
- 229960005424 cypermethrin Drugs 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 229960002483 decamethrin Drugs 0.000 description 1
- OWZREIFADZCYQD-NSHGMRRFSA-N deltamethrin Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OWZREIFADZCYQD-NSHGMRRFSA-N 0.000 description 1
- 229940019503 diflubenzuron Drugs 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- QLFZZSKTJWDQOS-YDBLARSUSA-N doramectin Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C3CCCCC3)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C QLFZZSKTJWDQOS-YDBLARSUSA-N 0.000 description 1
- 229960003997 doramectin Drugs 0.000 description 1
- CXEGAUYXQAKHKJ-NSBHKLITSA-N emamectin B1a Chemical compound C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](NC)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 CXEGAUYXQAKHKJ-NSBHKLITSA-N 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000004820 halides Chemical group 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 229960002418 ivermectin Drugs 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000005910 lambda-Cyhalothrin Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- KRQUFUKTQHISJB-UHFFFAOYSA-N profoxydim Chemical compound OC=1CC(C2CSCCC2)CC(=O)C=1C(CCC)=NOCC(C)OC1=CC=C(Cl)C=C1 KRQUFUKTQHISJB-UHFFFAOYSA-N 0.000 description 1
- RYVMUASDIZQXAA-UHFFFAOYSA-N pyranoside Natural products O1C2(OCC(C)C(OC3C(C(O)C(O)C(CO)O3)O)C2)C(C)C(C2(CCC3C4(C)CC5O)C)C1CC2C3CC=C4CC5OC(C(C1O)O)OC(CO)C1OC(C1OC2C(C(OC3C(C(O)C(O)C(CO)O3)O)C(O)C(CO)O2)O)OC(CO)C(O)C1OC1OCC(O)C(O)C1O RYVMUASDIZQXAA-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- AFJYYKSVHJGXSN-KAJWKRCWSA-N selamectin Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1C(/C)=C/C[C@@H](O[C@]2(O[C@@H]([C@@H](C)CC2)C2CCCCC2)C2)C[C@@H]2OC(=O)[C@@H]([C@]23O)C=C(C)C(=N\O)/[C@H]3OC\C2=C/C=C/[C@@H]1C AFJYYKSVHJGXSN-KAJWKRCWSA-N 0.000 description 1
- 229960002245 selamectin Drugs 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229920001909 styrene-acrylic polymer Polymers 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 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
- A01N25/32—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
- 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
- A01N25/30—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 characterised by the surfactants
-
- 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
- A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
Landscapes
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The use of at least one dipropylene glycol dibenzoate and/or diethylene glycol dibenzoate to reduce the eye irritation of an agrochemical composition caused by at least one active ingrediend and/or at least one emulsifier in the composition. Also claimed is a method of reducing eye irritation of a liquid composition comprising at least one active ingredient and at least one emulsifier, the method comprising including at least one dipropylene/diethylene glycol dibenzoate in the composition. The composition is preferably a liquid concentrate, in particular an emulsion concentrate (EC) formulation. Preferably the active ingredient is one or more of bifenthrin, clethodim, clomazone, pyriproxyfen, lufenron and/or abamectin.
Description
AN AGROCHEMCIAL COMPOSITION, A METHOD OF PREPARING THE SAME AND THE USE THEREOF
The present invention relates to an agrochemical composition. The present invention further relates to a method of preparing the aforementioned composition and its use in crop protection. The present invention is also related to the reduction of eye irritation caused by the agrochemical composition, in particular a liquid concentrate formulation of the composition.
Emulsifiable concentrate (EC) formulations are a very popular formulation type for the preparation and use of compositions comprising agrochemically active components. However, such formulations require substantial quantities of organic solvents, such as aromatic hydrocarbons, chlorinated hydrocarbons, and the like, together with anionic and non-ionic emulsifiers to stabilize the active ingredients in the formulations. With this combination of components, the formulated products are of a good quality and generally perform well in field applications. However, most of the products formulated in this manner cause severe eye irritation to users. As a result, such formulations are often classed as being hazardous. For example, emulsifiable concentrates are classified as Toxicity Category I (Cat I) in Brazil. Knowing that formulations labeled with “Toxicity Category I” may cause eye irritation, farmers and other end users are reluctant to purchase and use such products.
The prior art does not offer a solution for the problems of using solvents and emulsifiers in emulsion concentrate (EC) formulations. At present, commercial emulsion concentrate formulations cause severe eye irritation. As a result, attempts have been made to avoid the use organic solvents such as aromatic or chlorinated hydrocarbons, and instead use alternative solvents having reduced toxic effects. Examples of such alternative solvents are aliphatic hydrocarbons, alcohols, glycols, polyglycols, glycol ethers, ketones, as well as polar solvents with a high solvent power, such as gamma-butyrolactone, N-methyl pyrrolidone, and the like.
However, eye irritation is caused not only by the solvents, but can also be caused by active ingredients and emulsifiers present in the formulation. The emulsifiers, for example anionic emulsifiers, are important to increase spontaneous dispersibility of the formulation in water and stability of the diluted formulation. Calcium alkylbenzene sulfonate is one type of anionic emulsifier frequently used in emulsion concentrate formulations. However, these kind of anionic emulsifiers cause severe eye irritation. Consequently, even if the composition is formulated with solvents that are non-irritant to the eyes, the formulation may still cause severe eye irritation because of the presence of active ingredients and emulsifiers.
WO 02/045507 describes a microemulsifiable concentrate comprising a hydrophobic active ingredient and at least one surfactant dissolved in a solvent system comprising a hydrophobic water-insoluble alkyl alkanolate, as a first solvent, and a polyhydric alcohol or a condensate of polyhydric alcohols and mixtures thereof, as a second solvent. The formulations are reported to exhibit reduced eye irritation.
WO 2006/002984 discloses a liquid concentrate composition comprising a water-insoluble active ingredient, at least one organic solvent having a water solubility of at least 10 g/L, and at least one non-ionic block copolymer comprising at least one polyethylene oxide moiety and at least one hydrophobic polyether moiety. The organic solvent is capable of dissolving the active ingredient. The problem of eye irritation is not discussed or otherwise addressed in WO 2006/002984.
There is an ongoing need to find safe, preferably substantially inert, components for formulating liquid concentrates, with a view to providing a formulation which will not irritate the eyes. It would be advantageous if the formulation components could also reduce the irritancy of the active ingredients and emulsifiers to the eyes of users.
It has now been surprisingly found that certain dipropylene/diethylene glycol dibenzoates are not only non-irritant to the eyes, but also reduce the eye irritation caused by the active ingredients and emulsifiers present in the formulation.
Accordingly, in a first aspect, the present invention provides an agrochemical composition comprising at least one dipropylene/diethylene glycol dibenzoate, at least one active ingredient and at least one emulsifier.
Dipropylene/diethylene glycol dibenzoates are themselves not irritants. It has been found that the presence of the dipropylene/diethylene glycol dibenzoate in the agrochemical composition significantly reduces the toxicity of the formulation, in particular reducing the irritancy of the formulation to the eyes. In particular, it appears that the dipropylene/diethylene glycol dibenzoate reduces or substantially negates the irritancy of the active ingredients and emulsifiers to the eyes.
As described in more detail below, it has been found that dipropylene/diethylene glycol dibenzoate is effective in reducing the irritancy of liquid concentrate formuilations. Thus, the inclusion of dipropylene/diethylene glycol dibenzoate in liquid concentrates reduces the eye irritancy of the formulation. In addition, it has been found that the use of dipropylene/diethylene glycol dibenzoate in liquid concentrate pesticidal formulations is environmentally friendly.
The dipropylene/diethylene glycol dibenzoate is present in the composition of the present invention in an amount sufficient to reduce the irritancy of the other components in the composition, in particular the eye irritation of the active ingredients and emulsifiers present. The amount of dipropylene/diethylene glycol dibenzoate required will be determined by the particular active ingredients and emulsifiers employed in the composition and their amounts. The amount of the dipropylene/diethylene glycol dibenzoate required to reduce or eliminate the irritancy to the eyes of the formulation may be determined without undue experimentation by the skilled person, for example by trial and error.
The dipropylene/diethylene glycol dibenzoate is effective to reduce the eye irritancy of the active ingredient when present in a wide range of weight ratios to the active ingredient. The dipropylene/diethylene glycol dibenzoate is preferably present in an amount at least equal to or, more preferably in excess of the amount of the active ingredient. The weight ratio of the dipropylene/diethylene glycol dibenzoate to the active ingredient is preferably at least 1:1, in some preferred embodiments at least 1:2, in other preferred embodiments at least 1:3. In particular, the dipropylene/diethylene glycol dibenzoate is preferably present in an amount to provide a weight ratio of the active ingredient to the dipropylene/diethylene glycol dibenzoate from 1:1 to 1:100, preferably from 1:1 to 1:90, more preferably from 1:2 to 1:20, still more preferably from 1:3 to 1:15.
The dipropylene/diethylene glycol dibenzoate is effective in reducing the eye irritancy of emulsifiers in a wide range of weight ratios. In many embodiments, the dipropylene/diethylene glycol dibenzoate is present in the composition in an amount at least equal to, more preferably in excess, of the total amount of the emulsifier present. The weight ratio of the dipropylene/diethylene glycol dibenzoate to the total emulsifier content of the composition is preferably at least 0.1, more preferably at least 0.2. The weight ratio of the dipropylene/diethylene glycol dibenzoate to the total emulsifier content of the composition may be from 0.1 to 60, preferably from 0.2 to 60. In a number of embodiments, a weight ratio of from 0.3 to 10, more particularly from 0.4 to 8 has been found to be effective. Higher amounts of the dipropylene/diethylene glycol dibenzoate may be employed, for example in weight ratios to the emulsifier content of from 10 to 50. In many embodiments, a weight ratio of dipropylene/diethylene glycol dibenzoate to the emulsifier content of less than 15, more preferably less than 10 is effective.
The dipropylene/diethylene glycol dibenzoate may be present in the composition in an amount of at least 2% by weight, preferably from 10% by weight, more preferably from 20% by weight. In preferred embodiments, the dipropylene/diethylene glycol dibenzoate is present in the composition in an amount of from 2 to 90% by weight, preferably from 10 to 80% be weight, more preferably from 20 to 70% by weight of the composition.
The composition may comprise dipropylene glycol dibenzoate, diethylene glycol dibenzoate or a combination of dipropylene glycol dibenzoate and diethylene glycol dibenzoate.
As mentioned above, the present invention provides an agrochemical composition comprising at least one agrochemically active ingredient. It has been found that the presence of one or more dipropylene/diethylene glycol dibenzoates is effective in reducing the irritancy of a range of active ingredients. Suitable active ingredients for use in the composition of the present invention are well known in the art and are commercially available.
As noted above, the dipropylene/diethylene glycol dibenzoates have been found to be effective in reducing the toxicity, in particular the irritancy to eyes, of a range of active ingredients. In one embodiment, the composition of the present invention comprises, as an active ingredient clomazone (2-(2-chlorobenzyl)4,4-dimethyl-1,2-oxazolidin-3-one).
It has also been found that the dipropylene/diethylene glycol dibenzoates are effective in reducing the toxicity, in particular the irritancy to eyes, of pyrethroid ester acaricides and insecticides. Such pyrethroids are known in the art and include, for example, cyhalothrin ((RS)-a-cyano-3-phenoxybenzyl (Z)-(1RS,3RS)-3-(2-chloro3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate), cypermethrin ((RS)a-cyano-3-phenoxybenzyl (1/?S,3/?S;1RS,3SR)-3-(2,2-dichlorovinyl)-2,2-dimethyl cyclopropanecarboxylate), deltamethrin ((S)-a-cyano-3-phenoxybenzyl (1R,3R)-3(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate), lambda-cyhalothrin ((S)-acyano-3-phenoxybenzyl (Z)-(1R,3R)-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2dimethylcyclopropanecarboxylate and (R)-cyano-3-phenoxybenzyl (Z)-(1S,3S)-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropane carboxylate). A particularly suitable pyrethroid is bifenthrin.
In one embodiment, the composition of the present invention comprises, as an active ingredient pyriproxyfen (4-phenoxyphenyl (RS)-2-(2-pyridyloxy)propyl ether).
It has also been found that the dipropylene/diethylene glycol dibenzoates are effective in reducing the toxicity, in particular the irritancy to eyes, of cyclohexime oxime herbicides, including alloxydim (methyl (1RS)-3-[(E)-1 -(allyloxyimino)butyl]-4-hydroxy-6,6-dimethyl-2-oxocyclohex-3-enecarboxylate), butroxydim ((5RS)-5-(3-butyryl-2,4,6-trimethylphenyl)-2-[(EZ)-1-(ethoxyimino)propyl]3-hydroxycyclohex-2-en-1-one), clethodim ((5RS)-2-{(1EZ)-1-[(2E)-3-chloroallyloxy imino]propyl}-5-[(2RS)-2-(ethylthio)propyl]-3-hydroxycyclohex-2-en-1-one), cloproxydim ((5RS)-2-{(EZ)-1-[(2EZ)-3-chloroallyloxyimino]butyl}-5-[(2RS)-2-(ethyl thio)propyl]-3-hydroxycyclohex-2-en-1-one), cycloxydim ((5RS)-2-[(EZ)-1-(ethoxy imino)butyl]-3-hydroxy-5-[(3RS)-thian-3-yl]cyclohex-2-en-1-one), profoxydim ((5RS)-2 -{(EZ)-1-[(2RS)-2-(4-chlorophenoxy)propoxyimino]butyl}-3-hydroxy-5-[(3RS)-thian-3yl]cyclohex-2-en-1-one), sethoxydim ((5RS)-2-[(EZ)-1-(ethoxyimino)butyl]-5-[(2RS)2-(ethylthio)propyl]-3-hydroxycyclohex-2-en-1-one), tepraloxydim ((5RS)-2-{(EZ)-1[(2E)-3-chloroallyloxyimino]propyl}-3-hydroxy-5-perhydropyran-4-ylcyclohex-2 -en-1-one), and tralkoxydim ((RS)-2-[(EZ)-1-(ethoxyimino)propyl]-3hydroxy-5-mesitylcyclohex-2-en-1-one). The dipropylene/diethylene glycol dibenzoates are particularly effective in reducing the irritancy of clethodim.
It has further been found that the dipropylene/diethylene glycol dibenzoates are effective in reducing the toxicity, in particular the irritancy to eyes, of benzoylphenylurea chitin synthesis inhibitors , including bistrifluron (1-[2-chloro-3,5-bis(trifluoromethyl)phenyl]-3-(2,6-difluorobenzoyl)urea), chlorbenzuron (1-(2-chlorobenzoyl)-3-(4-chlorophenyl)urea), chlorfluazuron (1-[3,5 -dichloro-4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenyl]-3-(2,6-difluorobenzoyl) urea), dichlorbenzuron (1-(4-chlorophenyl)-3-(2,6-dichlorobenzoyl)urea), diflubenzuron (1-(4-chlorophenyl)-3-(2,6-difluorobenzoyl)urea), flucycloxuron (1-{a-[(EZ)-4-chloro-a-cyclopropylbenzylideneaminooxy]-p-tolyl}-3-(2,6-difluoro benzoyl)urea (ratio 50-80% (E)- and 50-20% (Z)-isomers), flufenoxuron (1-[4-(2-chloro-a,a,a-trifluoro-p-tolyloxy)-2-fluorophenyl]-3-(2,6-difluoro benzoyl)urea), hexaflumuron (1-[3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)phenyl] -3-(2,6-difluorobenzoyl)urea), lufenuron ((RS)-1-[2,5-dichloro-4-(1,1,2,3,3,3-hexa fluoropropoxy)phenyl]-3-(2,6-difluorobenzoyl)urea), novaluron ((RS)-1-[3-chloro-4(1,1,2-trifluoro-2-trifluoromethoxyethoxy)phenyl]-3-(2,6-difluorobenzoyl)urea), noviflumuron (1-{3,5-dichloro-2-fluoro-4-[(RS)-1,1,2,3,3,3-hexafluoropropoxy]phenyl}3-(2,6-difluorobenzoyl)urea), penfluron (1-(2,6-difluorobenzoyl)-3-(a,a,a-trifluorop-tolyl)urea), teflubenzuron (1-(3,5-dichloro-2,4-difluorophenyl)-3-(2,6-difluorobenzoyl) urea), and triflumuron (1-(2-chlorobenzoyl)-3-(4-trifluoromethoxyphenyl)urea). The dipropylene/diethylene glycol dibenzoates are particularly effective in reducing the irritancy of lufenuron.
It has further been found that the dipropylene/diethylene glycol dibenzoates are effective in reducing the toxicity, in particular the irritancy to eyes, of avermectin insecticides, acaracides and nematacides, including abamectin (mixture of > 80% (10E,14E,16E)-(1R,4S,5'S,6S,67?,8R,12S,13S,20R,21R,24S)-6'-[(S)-sec-butyl]-21,24 -dihydroxy-5', 11,13,22-tetramethyl-2-oxo-(3,7,19-trioxatetracyclo[15.6.1.148,o20'24] pentacosa-10,14,16,22-tetraene)-6-spiro-2'-(5',6'-dihydro-277-pyran)-12-yl 2,6-dideoxy-4-O-(2,6-dideoxy-3-O-methyl-a-L-arab/T7o-hexopyranosyl) -3-O-methyl-a-L-arab/T7o-hexopyranoside and < 20% (10E,14E,16E)(1R,4S,5'S,6S,67?,8R,12S,13S,20R,21R,24S)-21,24-dihydroxy-6'-isopropyl-5',11,13, 22-tetramethyl-2-oxo-(3,7,19-trioxatetracyclo[15.6.1.14’8.020’24]pentacosa-10,14,16,22tetraene)-6-spiro-2'-(5',6'-dihydro-277-pyran)-12-yl 2,6-dideoxy-4-O-(2,6-dideoxy3-O-methyl-a-L-arab/77o-hexopyranosyl)-3-O-methyl-a-L-arab/77o-hexopyranoside), doramectin ((10E, 14E, 16E)-(1 R,4S,5'S,6S,6'R,8R, 12S, 13S,20R,21 R,24S)-6'cyclohexyl-21,24-dihydroxy-5', 11,13,22-tetramethyl-2-oxo-(3,7,19-trioxatetracyclo[15. 6.1.14’8.020’24]pentacosa-10,14,16,22-tetraene)-6-spiro-2'-(5',6'-dihydro-2'H-pyran)12-yl 2,6-dideoxy-4-O-(2,6-dideoxy-3-O-methyl-a-L-arab/77O-hexopyranosyl)-3-Omethyl-a-L-arab/no-hexopyranoside), emamectin (mixture of > 90% (10E, 14E, 16E)-(1 R,4S,5'S,6S,6'R,8R, 12S, 13S,20R,21 R,24S)-6'-[(S)-sec-butyl]-21,24 -dihydroxy-5', 11,13,22-tetramethyl-2-oxo-(3,7,19-trioxatetracyclo[15.6.1.14’8.020’24]pen tacosa-10,14,16,22-tetraene)-6-spiro-2'-(5',6'-dihydro-277-pyran)-12-yl 2,6-dideoxy3-O-methyl-4-O-(2,4,6-trideoxy-3-O-methyl-4-methylamino-a-L-/yxo-hexapyranosyl)-a
-L-arab/no-hexapyranoside and < 10% (10E,14E,16E)(1R,4S,5'S,6S,67?,8R,12S,13S,20/?,21/?,24S)-21,24-dihydroxy-6'-isopropyl-5',11,13, 22-tetramethyl-2-oxo-(3,7,19-trioxatetracyclo[15.6.1.14’8.020’24]pentacosa-10,14,16,22tetraene)-6-spiro-2'-(5',6'-dihydro-277-pyran)-12-yl 2,6-dideoxy-3-O-methyl-4-O(2,4,6-trideoxy-3-O-methyl-4-methylamino-a-L-/yxo-hexapyranosyl)-a-L-arab/77o-hexa pyranoside), eprinomection (mixture of (10E,14E,16E)-(1/?,4S,5'S,6S,67?,8R, 12S,13S,20R,21R,24S)-6'-[(S)-sec-butyl]-21,24-dihydroxy-5',11,13,22-tetramethyl-2-o xo-(3,7,19-trioxatetracyclo[15.6.1.14’8.020’24]pentacosa-10,14,16,22-tetraene)-6-spiro2'-(5',6'-dihydro-277-pyran)-12-yl 4-O-(4-acetamido-2,4,6-trideoxy-3-O-methyla-L-/yxo-hexopyranosyl)-2,6-dideoxy-3-O-methyl-a-L-arab/T7o-hexopyranoside (major component) and (10E,14E,16E)-(1R,4S,5'S,6S,67?,8/?,12S,13S,20R, 21/?,24S)-21,24-dihydroxy-6'-isopropyl-5',11,13,22-tetramethyl-2-oxo-(3,7,19-trioxatet racyclo[15.6.1.14’8.020’24]pentacosa-10,14,16,22-tetraene)-6-spiro-2'-(5',6'-dihydro-277 -pyran)-12-yl 4-O-(4-acetamido-2,4,6-trideoxy-3-O-methyl-a-L-/yxohexopyranosyl)-2,6-dideoxy-3-O-methyl-a-L-arab/no-hexopyranoside (minor component)), ivermectin (mixture of (10E,14E,16E)-(1/?,4S,5'S,6/?,67?,8R,12S, 13S.20K.21 R,24S)-6'-[(S)-sec-butyl]-21,24-dihydroxy-5', 11,13,22-tetramethyl-2-oxo-( 3,7,19-trioxatetracyclo[15.6.1.14’8.020’24]pentacosa-10,14,16,22-tetraene)-6-spiro-2'-(t etrahydropyran)-12-yl 2,6-dideoxy-4-O-(2,6-dideoxy-3-O-methyl-a-L-arab/nohexopyranosyl)-3-O-methyl-a-L-arab/no-hexopyranoside and (10E, 14E, 16E)-(1 R,4S, 5'S,6R,6'R,8R, 12S, 13S,20R,21 R,24S)-21,24-dihydroxy-6'-isopropyl-5', 11,13,22-tetra methyl-2-oxo-(3,7,19-trioxatetracyclo[15.6.1.14’8.020’24]pentacosa-10,14,16,22-tetraen e)-6-spiro-2'-(tetrahydropyran)-12-yl 2,6-dideoxy-4-O-(2,6-dideoxy-3-O-methyl-a-Larab/no-hexopyranosylj-S-O-methyl-a-L-arab/no-hexopyranoside), and selamectin ((10E,14E,16E,21Z)-(1 R,4S, 5' S,6R,6'S, 8R,12S,13S,20R,21 R,24S)-6'-cyclohexyl-24hydroxy-21 -hydroxyimino-5', 11,13,22-tetramethyl-2-oxo-(3,7,19-trioxatetracyclo[15.6.
1.14’8.020’24]pentacosa-10,14,16,22-tetraene)-6-spiro-2'-(tetrahydropyran)-12-yl 2,6-dideoxy-3-O-methyl-a-L-arab/T7o-hexopyranoside). The dipropylene/diethylene glycol dibenzoates are particularly effective in reducing the irritancy of abamectin.
It has been found that the composition of the present invention is particularly effective when the active ingredient is selected from clomazone, bifenthrin, pyriproxyfen, clethodim, lufenuron, abamectin and mixtures thereof.
The present invention provides an agrochemical composition further comprising at least one emulsifier. Suitable emulsifiers for use in the composition are well known in the art and are commercially available. The emulsifier or emulsifier mixture is selected to have good emulsifying, dispersing and wetting abilities in the formulation employed. The emulsifier may be selected from non-ionic emulsifiers, ionic emulsifiers, cationic emulsifiers and mixtures thereof.
Preferred non-ionic emulsifiers are those selected from alcohol alkoxylates, alkylphenol ethoxylates, alkylpolysaccharides, amine ethoxylates, castor oil ethoxylates, sorbitan fatty acid ester ethoxylates, and polyoxyethylene fatty acids.
Preferred anionic emulsifiers are water-soluble soaps as well as water-soluble synthetic emulsifiers. Typical examples of anionic emulsifiers are selected from amine alkylbenzenesulfonate, ammonium dodecylbenzene sulfonate, calcium alkylsulphonate, and calcium alkylbenzenesulfonate.
Preferred cationic emulsifiers in the composition of the present invention may be quaternary ammonium salts having the following general formula:
in which Ri, R2, R3 or R4each represents at least one Cs to C22 alkyl radical, or R1, R2, R3 or R4each represents an unsubstituted or halogenated lower alkyl, benzyl, or hydroxyl- lower alkyl radicals; and X represents a halide, for example a chlorine ion, methyl sulfate or ethyl sulfate. Examples of preferred cationic emulsifiers are polyoxyethylene quaternary and polyoxyethylene tallow ethylmonium ethosulfate, stearyltrimethylammonium chloride, benzyl bis(2-chloroethyl)ethylammonium bromide.
The emulsifier or emulsifier mixture may be present in the composition in any suitable amount. Preferably, the emulsifier is present in the composition in an amount of at least 5% by weight, more preferably at least 10% by weight, still more preferably at least 15% by weight. Preferably, the one or more emulsifiers are 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 of the composition. An amount of one or more emulsifiers of from 20 to 30% by weight of the composition has been found to be particularly suitable in many embodiments.
In addition to dipropylene/diethylene glycol dibenzoate, at least one active ingredient and at least one emulsifier, the compositions of the present invention may also comprise other components as is known in the art, depending upon the type of formulation being employed.
For example, the composition may comprise one or more solvents, in particular one or more polar or non-polar organic solvents. Suitable solvents are known in the art and are commercially available. Suitable polar or non-polar organic solvents include alcohols, such as benzyl alcohol, alkyl pyrrolidones, such as
N-methylprrolidone, N-octylpyrrolidone, or one or more lactones, such as γ-butyrolactone; aromatic hydrocarbons and mixtures thereof, such as the commercially available solvent compositions SOLVESSO™100 and SOLVESSO™200, and dimethyl sulfoxide.
Further components that may be included in the composition are well known in the art and include one or more stabilizers, one or more thickeners, and the like. Such components are commercially available and their uses in formulating the agrochemical compositions are recognized and understood by the person skilled in the art.
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 emulsifiable concentrate (EC) formulation. The liquid concentrate formulations may comprise active ingredients that are sparingly water-soluble or water-insoluble. The liquid concentrate formulations are preferably those for dispersion in water, prior to use.
In a further aspect, the present invention provides a liquid concentrate composition comprising at least one dipropylene/diethylene glycol dibenzoate, at least one active ingredient and at least one emulsifier.
The present invention also provides, in a further aspect, a method for preparing an agrochemical composition, the method comprising combining at least one dipropylene/diethylene glycol dibenzoate with at least one active ingredient and at least one emulsifier.
The compositions of the present invention may be prepared using techniques known in the art. A particularly preferred method for preparing the liquid concentrate composition is as follows:
Each component is provided according to the weight fraction required in the final composition. First, a solvent and dipropylene/diethylene glycol dibenzoate are added to a suitable mixing vessel, for example a blending tank, and mixed to form a mixture. The active ingredient is then added to the mixture and mixed continuously (typically for about 30 minutes) until the active ingredient dissolves completely in the solvent. Thereafter, the one or more emulsifiers and the further components, if present, are added to the mixture and mixed (typically for about an hour) to ensure homogeneity.
In a further aspect, the present invention provides the use of at least one dipropylene/diethylene glycol dibenzoate to reduce the eye irritancy of an active ingredient and an emulsifier in an agrochemical formulation.
In a further aspect, the present invention provides a method for reducing the eye irritation of liquid formulations caused by the active ingredients and emulsifiers, the method comprising adding at least one dipropylene/diethylene glycol dibenzoate to the formulation in an amount sufficient to reduce the eye irritancy of the formulation.
In a still further aspect, the present invention provides a method for treating pests at a locus comprising applying to the locus a composition as hereinbefore described.
Embodiments of the present invention will now be described, for illustration purposes only, by way of the following examples.
EXAMPLES
In each of the following examples, a composition was prepared according to the following general methodology:
In general, each component was added to a vessel in an amount based upon the particular composition recipe indicate. More particularly, first, the solvent and dipropylene/diethylene glycol dibenzoate were added to a blending tank in the specified amounts and mixed to form a mixture. At least one active ingredient was added to the mixture and mixed continuously for about 30 minutes until the active ingredient was dissolved completely. Thereafter, the emulsifier was added to the blending tank and the resulting mixture mixed continuously for about an hour until the mixture was uniform, after which mixing was stopped. Finally, the mixture was discharged from the blending tank.
The eye irritation potential of each formulation 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 etal. ATLA 24 (1996), pp. 741-858).
In the HET-CAM Test, a chorioallantoic membrane (CAM) was treated with samples of each composition. The chorioallantoic membrane was then observed for 5 minutes. The severity of haemorrhage, lysis and coagulation were examined. The samples were categorized as follows:
Category 0 (Cat 0):
Category I (Cat I):
Category II (Cat II):
Category III (Cat III):
strongly irritant irritant moderate irritant non-irritant
Samples and controls were prepared for each formulation. The eye irritation potential of the samples and controls were examined as mentioned above. In each example, the control composition is identical to the sample composition, with the exception that dipropylene/diethylene glycol dibenzoate was omitted.
Example 1
Emulsion concentrate compositions Sample 1 and Control 1 were prepared according to the recipe specified in Table 1 below. The ratio of bifenthrin and dipropylene glycol dibenzoate of Sample 1 was approximately 1:13. The eye irritancy of Sample 1 was compared with that of Control 1 (that is the composition of Sample 1 without the addition of dipropylene glycol dibenzoate).
Table 1
| Content | Sample 1: Bifenthrin EC with dipropylene glycol dibenzoate | Control 1: Bifenthrin EC without dipropylene glycol dibenzoate |
| Active ingredient: Bifenthrin tech (Obtained from Jiangsu Yangnong) | 50 kg (as pure) | 50 kg (as pure) |
| Emulsifier: Calcium dodecylphenylsulfonate (70B) (Obtained from Rhodia) | 100 kg | 100 kg |
| Emulsifier: TWEEN®80 (Sorbitan monooleate ethoxylate) | 100 kg | 100 kg |
| Solvent: SOLVESSO™100 | 100 kg | 750 kg |
| Eye irritation reducer: Dipropylene glycol dibenzoate | 650 kg | 0 kg |
| Total | 1000 kg | 1000 kg |
Example 2
Emulsion concentrate compositions Sample 2 and Control 2 were prepared according to the recipe set out in Table 2 below. The ratio of bifenthrin and diethylene glycol dibenzoate of Sample 2 was approximately 1:1. The eye irritation of Sample 2 was compared with that of Control 2 (without the addition of diethylene glycol dibenzoate).
Table 2
| Content | Sample 2: Bifenthrin EC with diethylene glycol dibenzoate | Control 2: Bifenthrin EC without diethylene glycol dibenzoate |
| Active ingredient: Bifenthrin tech | 100 kg (as pure) | 100 kg (as pure) |
| Emulsifier: ATLOX™3300B (amine alkylbenzenesulfonate) (Obtained from Croda) | 100 kg | 100 kg |
| Emulsifier: SPAN®20 (Sorbitan monolaurate) (Obtained from Croda) | 100 kg | 100 kg |
| Solvent: SOLVESSO™100 | 600 kg | 700 kg |
| Eye irritation reducer: Diethylene glycol dibenzoate | 100 kg | 0 kg |
| Total | 1000 kg | 1000 kg |
Example 3
Emulsion concentrate compositions Sample 3 and Control 3 were prepared with components according to Table 3 below. The ratio of bifenthrin and dipropylene glycol dibenzoate of Sample 3 was approximately 1:2. The eye irritation of Sample 3 5 was compared with that Control 3 (without the addition of dipropylene glycol dibenzoate).
Table 3
| Content | Sample 3: Bifenthrin EC with dipropylene glycol dibenzoate | Control 3: Bifenthrin EC without dipropylene glycol dibenzoate |
| Active ingredient: Bifenthrin tech | 80 kg (as pure) | 80 kg (as pure) |
| Emulsifier: ATLOX™4838B (Calcium alkyl sulphonate) (Obtained from Croda) | 100 kg | 100 kg |
| Emulsifier: TWEEN®80 Sorbitan monooleate ethoxylate (Obtained from Croda) | 100 kg | 100 kg |
| Solvent: SOLVESSO™200 (Obtained from Exxon) | 560 kg | 720 kg |
| Eye irritation reducer: dipropylene glycol dibenzoate | 160 kg | 0 kg |
| Total | 1000 kg | 1000 kg |
Example 4
Emulsion concentrate compositions Sample 4 and Control 4 were prepared with components as set out in Table 4 below. The ratio of clethodim and diethylene glycol dibenzoate of Sample 4 was approximately 1:3. The eye irritation of Sample 4 was compared with that of Control 4 (without the addition of diethylene glycol dibenzoate).
Table 4
| Content | Sample 4: Clethodim EC (with diethylene glycol dibenzoate) | Control 4: Clethodim EC (without diethylene glycol dibenzoate) |
| Active ingredient: | 50 kg (as pure) | 50 kg (as pure) |
| Clethodim tech | ||
| (Obtained from Shandong Xianda) | ||
| Emulsifier: Calcium dodecylphenylsulfonate (70B) (Obtained from Rhodia) | 100 kg | 100 kg |
| Emulsifier: EL360 Castor oil ethoxylate (Obtained from Clariant) | 100 kg | 100 kg |
| Solvent: Benzyl alcohol | 600 kg | 750 kg |
| Eye irritation reducer: Diethylene glycol dibenzoate | 150 kg | 0 kg |
| Total | 1000 kg | 1000 kg |
Example 5
Emulsion concentrate compositions Sample 5 and Control 5 were prepared with components according to Table 5. The ratio of clomazone and dipropylene glycol dibenzoate of Sample 5 was approximately 1:6. The eye irritation of Sample 5 was compared with that of Control 5 (without the addition of dipropylene glycol dibenzoate).
Table 5
| Content | Sample 5: Clomazone EC (with dipropylene glycol dibenzoate) | Control 5: Clomazone EC (without dipropylene glycol dibenzoate) |
| Active ingredient: Clomazone tech (Obtained from Shandong Xianda) | 100 kg (as pure) | 100 kg (as pure) |
| Emulsifier: Calcium dodecylphenylsulfonate (70B) (Obtained from Rhodia) | 100 kg | 100 kg |
| Emulsifier: TWEEN®80 Sorbitan monooleate ethoxylate (Obtained from Croda) | 100 kg | 100 kg |
| Solvent: Dimethyl sulfoxide | 100 kg | 700 kg |
| Eye irritation reducer: dipropylene glycol dibenzoate | 600 kg | 0 kg |
| Total | 1000 kg | 1000 kg |
Example 6
Emulsion concentrate compositions Sample 6 and Control 6 were prepared with components according to Table 6 below. The ratio of pyriproxyfen and dipropylene glycol dibenzoate of Sample 6 was approximately 1:5. The eye irritation of Sample 6 5 was compared with that of Control 6 (without the addition of dipropylene glycol dibenzoate).
Table 6
| Content | Sample 6: pyriproxyfen EC (with dipropylene glycol dibenzoate) | Control 6: pyriproxyfen EC (without dipropylene glycol di benzoate) |
| Active ingredient: pyriproxyfen tech (Obtained from Nantong shizhuang) | 100 kg (as pure) | 100 kg (as pure) |
| Emulsifier: Calcium dodecylphenylsulfonate (70B) (Obtained from Rhodia) | 100 kg | 100 kg |
| Emulsifier: EL360 Ethoxylated soybean oil (Obtained from Clariant) | 100 kg | 100 kg |
| Solvent: Dimethyl sulfoxide | 100 kg | 700 kg |
| Eye irritation reducer: Dipropylene glycol dibenzoate | 600 kg | |
| Total | 1000 kg | 1000 kg |
Example 7
Emulsion concentrate compositions Sample 7 and Control 7 were prepared with components as set out in Table 7 below. The ratio of pyriproxyfen and diethylene glycol dibenzoate of Sample 7 was approximately 1:10. The eye irritation of Sample 7 was compared with that of Control 7 (without the addition of diethylene glycol dibenzoate).
Table 7
| Content | Sample 7: pyriproxyfen EC (with diethylene glycol dibenzoate) | Control 7: pyriproxyfen EC (without diethylene glycol dibenzoate) |
| Active ingredient: Pyriproxyfen tech (Obtained from Nantong shizhuang) | 50 kg (as pure) | 50 kg (as pure) |
| Emulsifier: ATLOX METASPERSE™100L (styrene acrylic polymer) (Obtained from Croda) | 100 kg | 100 kg |
| Emulsifier: TWEEN®80 Sorbitan monooleate ethoxylate (Obtained from Croda) | 100 kg | 100 kg |
| Solvent: SOLVESSO™200 (Obtained from Exxon) | 250 kg | 750 kg |
| Eye irritation reducer: diethylene glycol dibenzoate | 500 kg | 0 kg |
| Total | 1000 kg | 1000 kg |
Example 8
Emulsion concentrate compositions Sample 8 and Control 8 were prepared with components according to Table 8 below. The ratio of pyriproxyfen and dipropylene glycol dibenzoate of Sample 7 was approximately 1:16. The eye irritation of Sample 8 was compared with that of Control 8 (without the addition of dipropylene glycol dibenzoate).
Table 8
| Content | Sample 8: pyriproxyfen EC (with dipropylene glycol dibenzoate) | Control 8: pyriproxyfen EC (without dipropylene glycol dibenzoate) |
| Active ingredient: pyriproxyfen tech | 50 kg (as pure) | 50 kg (as pure) |
| Emulsifier: Calcium dodecylphenylsulfonate (70B) | 50 kg | 50 kg |
| Emulsifier: TWEEN®80 (Sorbitan monooleate ethoxylate) | 50 kg | 50 kg |
| Solvent: Benzyl alcohol | 50 kg | 850 kg |
| Eye irritation reducer: dipropylene glycol dibenzoate | 800 kg | 0 kg |
| Total | 1000 kg | 1000 kg |
Example 9
Emulsion concentrate compositions Sample 9 and Control 9 were prepared according to the recipe of Table 9. The ratio of pyriproxyfen and dipropylene glycol dibenzoate of Sample 9 was approximately 1:20. Eye irritation of Sample 9 was compared with that of Control 9 (without the addition of dipropylene glycol dibenzoate).
Table 9
| Content | Sample 8: pyriproxyfen EC (with dipropylene glycol dibenzoate) | Control 8: pyriproxyfen EC (without dipropylene glycol dibenzoate) |
| Active ingredient: pyriproxyfen tech | 20 kg (as pure) | 20 kg (as pure) |
| Emulsifier: Calcium dodecylphenylsulfonate | 10 kg | 10 kg |
| Emulsifier: TWEEN®80 (Sorbitan monooleate ethoxylate) | 20 kg | 20 kg |
| Solvent: Dimethyl sulfoxide | 550 kg | 950 kg |
| Eye irritation reducer: dipropylene glycol dibenzoate | 400 kg | 0 kg |
| Total | 1000 kg | 1000 kg |
Example 10
Emulsion concentrate compositions Sample 10 and Control 10 were prepared according to the recipe of Table 10 below. The ratio of lufenuron and dipropylene glycol dibenzoate of Sample 10 was approximately 1:30. The eye irritation of
Sample 10 was compared with that of Control 10 (without the addition of dipropylene glycol dibenzoate).
Table 10
| Content | Sample 10: lufenuron EC (with dipropylene glycol dibenzoate) | Control 10: lufenuron EC (without dipropylene glycol di benzoate) |
| Active ingredient: Lufenuron tech (Obtained from Shanghai shitou) | 20 kg (as pure) | 20 kg (as pure) |
| Emulsifier: Calcium dodecylphenylsulfonate (70B) | 100 kg | 100 kg |
| Emulsifier: TWEEN®80 (Sorbitan monooleate ethoxylate) | 100 kg | 100 kg |
| Solvent: Benzyl alcohol | 100 kg | 780 kg |
| Eye irritation reducer: dipropylene glycol dibenzoate | 680 kg | 0 kg |
| Total | 1000 kg | 1000 kg |
Example 11
Emulsion concentrate compositions Sample 11 and Control 11 were prepared according to the recipe of Table 11. The ratio of abmectin and dipropylene glycol dibenzoate of Sample 11 was approximately 1:90. The eye irritation of Sample 11 5 was compared with that of Control 11 (without the addition of dipropylene glycol dibenzoate).
Table 11
| Content | Sample 11: Abamectin EC (with dipropylene glycol di benzoate) | Control 11: Abamectin EC (without dipropylene glycol di benzoate) |
| Active ingredient: Abmectin tech (Obtained from Hebei weiyuan) | 10 kg (as pure) | 10 kg (as pure) |
| Emulsifier: Calcium dodecylphenylsulfonate (70B) | 10 kg | 10 kg |
| Emulsifier: TWEEN®80 (Sorbitan monooleate ethoxylate) | 10 kg | 10 kg |
| Solvent: Dimethyl sulfoxide | 70 kg | 970 kg |
| Eye irritation reducer: dipropylene glycol dibenzoate | 900 kg | 0 kg |
| Total | 1000 kg | 1000 kg |
Example 12
Emulsion concentrate compositions Sample 12 and Control 12 were prepared according to the recipe of Table 12. The ratio between bifenthrin and the combined dipropylene glycol dibenzoate and diethylene glycol dibenzoate of Sample 12 was 5 approximately 1:5. The eye irritation of Sample 12 was compared with that of
Control 12 (without the addition of dipropylene glycol dibenzoate and diethylene glycol dibenzoate).
Table 12
| Content | Sample 12: Bifenthrin EC (with dipropylene glycol dibenzoate and diethylene glycol dibenzoate) | Control 12: Bifenthrin EC (without dipropylene glycol dibenzoate and diethylene glycol dibenzoate) |
| Active ingredient: Bifenthrin tech (Obtained from Jiangsu Yangnong) | 100 kg (as pure) | 100 kg (as pure) |
| Emulsifier: Calcium dodecylphenylsulfonate (70B) | 100 kg | 100 kg |
| Emulsifier: TWEEN®80 (Sorbitan monooleate ethoxylate) | 100 kg | 100 kg |
| Solvent: SOLVESSO™200 | 200 kg | 700 kg |
| Eye irritation reducer: Dipropylene glycol dibenzoate | 200 kg | 0 kg |
| Eye irritation reducer: Diethylene glycol dibenzoate | 300 kg | 0 kg |
| Total | 1000 kg | 1000 kg |
Example 13
The eye irritation potential of the compositions of the Samples and Controls of Examples 1 to 12 was determined as described above. The performance of the compositions of the Samples and Controls was categorized as follows:
Category 0 (Cat 0):
Category I (Cat I):
Category II (Cat II):
Category III (Cat III):
strongly irritant irritant moderate irritant non-irritant
The results are listed in Table 13 below.
Table 13
| Samples and Controls | Results |
| Sample 1 | Cat III |
| Control 1 | Cat 0 |
| Sample 2 | Cat III |
| Control 2 | Cat 0 |
| Sample 3 | Cat III |
| Control 3 | Cat 0 |
| Sample 4 | Cat III |
| Control 4 | Cat 0 |
| Sample 5 | Cat III |
| Control 5 | Cat 0 |
| Sample 6 | Cat III |
| Control 6 | Cat 0 |
| Sample 7 | Cat III |
| Control 7 | Cat 0 |
| Sample 8 | Cat III |
| Control 8 | Cat 0 |
| Sample 9 | Cat III |
| Control 9 | Cat 0 |
| Sample 10 | Cat III |
| Control 10 | Cat 0 |
| Sample 11 | Cat III |
| Control 11 | Cat 0 |
| Sample 12 | Cat III |
| Control 12 | Cat 0 |
| SOLVESSO™100 | Cat III |
| SOLVESSO™200 | Cat II |
| Dimethyl sulfoxide | Cat III |
| Benzyl alcohol | Cat II |
From the results set out in Table 13, it can be seen that dipropylene glycol dibenzoate and diethylene glycol dibenzoate, whether used alone or in combination, were very effective in significantly reducing the eye irritation potential of the compositions.
Aspects and embodiments of the present invention are summarized by way of the following numbered clauses:
1. An agrochemical composition comprising at least one dipropylene/diethylene glycol dibenzoate, at least one active ingredient and at least one emulsifier.
2. The composition according to clause 1, wherein the dipropylene/diethylene glycol dibenzoate is present in an amount of from 2% to 90% by weight of the composition.
3. The composition according to clause 2, wherein the dipropylene/diethylene glycol dibenzoate is present in an amount of from 10% to 80% by weight of the composition.
4. The composition according to clause 3, wherein the dipropylene/diethylene glycol dibenzoate is present in an amount of from 20% to 70% by weight of the composition.
5. The composition according to any preceding clause, wherein the weight ratio of the active ingredient and dipropylene/diethylene glycol dibenzoate is from 1:1 to 1:90.
6. The composition according to clause 5, wherein the weight ratio of the active ingredient and dipropylene/diethylene glycol dibenzoate is from 1:1 to 1:50.
7. The composition according to clause 6, wherein the weight ratio of the active ingredient and dipropylene/diethylene glycol dibenzoate is from 1:2 to 1:20.
8. The composition according to clause 7, wherein the weight ratio of the active ingredient and dipropylene/diethylene glycol dibenzoate is from 1:3 to 1:15.
9. The composition according to any preceding clause, wherein the active ingredient comprises a compound selected from clomazone, a pyrethroid ester, a cyclohexime oxime, a benzoylphenylurea chitin synthesis inhibitor, and an avermectin.
10. The composition according to clause 9, wherein the active ingredient comprises a compound selected from bifenthrin, pyriproxyfen, clethodim, clomazone, abamectin and lufenuron.
11. The composition according to any preceding clause, wherein the emulsifier comprises a non-ionic emulsifier.
12. The composition according to clause 11, wherein the non-ionic emulsifier is selected from an alcohol alkoxylate, an alkylphenol ethoxylate, an alkylpolysaccharide, an amine ethoxylate, a castor oil ethoxylate, a sorbitan fatty acid ester ethoxylate and a polyoxyethylene fatty acid.
13. The composition according to any preceding clause, wherein the emulsifier comprises an ionic emulsifier.
14. The composition according to clause 13, wherein the ionic emulsifier is selected from an amine alkylbenzenesulfonate, an ammonium dodecylbenzene sulfonate, a calcium alkylsulphonate and a calcium alkylbenzenesulfonate.
15. The composition according to any preceding clause, wherein the emulsifier comprises a cationic emulsifier.
16. The composition according to clause 15, wherein the cationic emulsifier is selected from polyoxyethylene quaternary and polyoxyethylene tallow ethylmonium ethosulfate, stearyltrimethylammonium chloride and benzyl bis(2-chloroethyl)ethylammonium bromide.
17. The composition according to any preceding clause, wherein the at least one dipropylene/diethylene glycol dibenzoate is diethylene glycol dibenzoate or dipropylene glycol dibenzoate.
18. The composition according to any of clauses 1 to 16, wherein the at least one dipropylene/diethylene glycol dibenzoate comprises a mixture of diethylene glycol dibenzoate and dipropylene glycol dibenzoate.
19. The composition according to any preceding clause, wherein the composition is a liquid concentrate.
20. The composition according to clause 19, wherein the composition is an emulsificable concentrate (EC) formulation.
21. The use of at least one dipropylene/diethylene glycol dibenzoate to reduce the eye irritation of an agrochemical composition caused by at least one active ingredient and/or at least one emulsifier in the composition.
22. The use according to clause 21, wherein the dipropylene/diethylene glycol dibenzoate is combined with the active ingredient and emulsifier in the composition.
23. The use according to either of clauses 21 or 22, wherein the active ingredient comprises a compound selected from clomazone, a pyrethroid ester, a cyclohexime oxime, a benzoylphenylurea chitin synthesis inhibitor, and an avermectin.
24. The use according to clause 23, wherein the active ingredient comprises a compound selected from bifenthrin, pyriproxyfen, clethodim, clomazone, abamectin and lufenuron.
25. The use according to any of clauses 21 to 24, wherein the emulsifier comprises a non-ionic emulsifier.
26. The use according to clause 25, wherein the non-ionic emulsifier is selected from an alcohol alkoxylate, an alkylphenol ethoxylate, an alkylpolysaccharide, an amine ethoxylate, a castor oil ethoxylate, a sorbitan fatty acid ester ethoxylate and a polyoxyethylene fatty acid.
27. The use according to any of clauses 21 to 26, wherein the emulsifier comprises an ionic emulsifier.
28. The use according to clause 27, wherein the ionic emulsifier is selected from an amine alkylbenzenesulfonate, an ammonium dodecylbenzene sulfonate, a calcium alkylsulphonate and a calcium alkylbenzenesulfonate.
29. The use according to any of clauses 21 to 26, wherein the emulsifier comprises a cationic emulsifier.
30. The use according to clause 29, wherein the cationic emulsifier is selected from polyoxyethylene quaternary and polyoxyethylene tallow ethylmonium ethosulfate, stearyltrimethylammonium chloride and benzyl bis(2-chloroethyl)ethylammonium bromide.
31. The use according to any of clauses 21 to 30, wherein the at least one dipropylene/diethylene glycol dibenzoate is diethylene glycol dibenzoate or dipropylene glycol dibenzoate.
32. The use according to any of clauses 21 to 30, wherein the at least one dipropylene/diethylene glycol dibenzoate comprises a mixture of diethylene glycol dibenzoate and dipropylene glycol dibenzoate.
33. A method of reducing eye irritation of a liquid composition comprising at least one active ingredient and at least one emulsifier, the method comprising including in the composition at least one dipropylene/diethylene glycol dibenzoate in the composition.
34. The method according to clause 33, wherein the active ingredient comprises a compound selected from clomazone, a pyrethroid ester, a cyclohexime oxime, a benzoylphenylurea chitin synthesis inhibitor, and an avermectin.
35. The method according to clause 34, wherein the active ingredient comprises a compound selected from bifenthrin, pyriproxyfen, clethodim, clomazone, abamectin and lufenuron.
36. The method according to any of clauses 33 to 35, wherein the emulsifier comprises a non-ionic emulsifier.
37. The method according to clause 36, wherein the non-ionic emulsifier is selected from an alcohol alkoxylate, an alkylphenol ethoxylate, an alkylpolysaccharide, an amine ethoxylate, a castor oil ethoxylate, a sorbitan fatty acid ester ethoxylate and a polyoxyethylene fatty acid.
38. The method according to any of clauses 33 to 37, wherein the emulsifier comprises an ionic emulsifier.
39. The method according to clause 38, wherein the ionic emulsifier is selected from an amine alkylbenzenesulfonate, an ammonium dodecylbenzene sulfonate, a calcium alkylsulphonate and a calcium alkylbenzenesulfonate.
40. The method according to any of clauses 33 to 39, wherein the emulsifier comprises a cationic emulsifier.
41. The method according to clause 40, wherein the cationic emulsifier is selected from polyoxyethylene quaternary and polyoxyethylene tallow ethylmonium ethosulfate, stearyltrimethylammonium chloride and benzyl bis(2-chloroethyl)ethylammonium bromide.
42. The method according to any of clauses 33 to 41, wherein the at least one dipropylene/diethylene glycol dibenzoate is diethylene glycol dibenzoate or dipropylene glycol dibenzoate.
43. The method according to any of clauses 33 to 42, wherein the at least one dipropylene/diethylene glycol dibenzoate comprises a mixture of diethylene glycol dibenzoate and dipropylene glycol dibenzoate.
44. The method according to any of clauses 33 to 43, wherein the composition is a liquid concentrate.
45. The method according to clause 44, wherein the composition is an emulsificable concentrate (EC) formulation.
46. A method of treating pests at a locus comprising applying to the locus a composition according to any of clauses 1 to 20.
47. A composition substantially as hereinbefore described.
48. The use of at least one dipropylene/diethylene glycol dibenzoate substantially as hereinbefore described.
49. A method of reducing eye irritancy of a composition substantially as hereinbefore 5 described.
50. A method of treating pests at a locus substantially as hereinbefore described.
Claims (25)
1. The use of at least one dipropylene/diethylene glycol dibenzoate to reduce the eye irritation of an agrochemical composition caused by at least one active ingredient and/or at least one emulsifier in the composition.
2. The use according to claim 1, wherein the dipropylene/diethylene glycol dibenzoate is combined with the active ingredient and emulsifier in the composition.
3. The use according to either of claims 1 or 2, wherein the active ingredient comprises a compound selected from clomazone, a pyrethroid ester, a cyclohexime oxime, a benzoylphenylurea chitin synthesis inhibitor, and an avermectin.
4. The use according to claim 3, wherein the active ingredient comprises a compound selected from bifenthrin, pyriproxyfen, clethodim, clomazone, abamectin and lufenuron.
5. The use according to any of claims 1 to 4, wherein the emulsifier comprises a non-ionic emulsifier.
6. The use according to claim 5, wherein the non-ionic emulsifier is selected from an alcohol alkoxylate, an alkylphenol ethoxylate, an alkylpolysaccharide, an amine ethoxylate, a castor oil ethoxylate, a sorbitan fatty acid ester ethoxylate and a polyoxyethylene fatty acid.
7. The use according to any of claims 1 to 6, wherein the emulsifier comprises an ionic emulsifier.
8. The use according to claim 7, wherein the ionic emulsifier is selected from an amine alkylbenzenesulfonate, an ammonium dodecylbenzene sulfonate, a calcium alkylsulphonate and a calcium alkylbenzenesulfonate.
9. The use according to any of claims 1 to 6, wherein the emulsifier comprises a cationic emulsifier.
10. The use according to claim 9, wherein the cationic emulsifier is selected from polyoxyethylene quaternary and polyoxyethylene tallow ethylmonium ethosulfate, stearyltrimethylammonium chloride and benzyl bis(2-chloroethyl)ethylammonium bromide.
11. The use according to any of claims 1 to 10, wherein the at least one dipropylene/diethylene glycol dibenzoate is diethylene glycol dibenzoate or dipropylene glycol dibenzoate.
12. The use according to any of claims 1 to 11, wherein the at least one dipropylene/diethylene glycol dibenzoate comprises a mixture of diethylene glycol dibenzoate and dipropylene glycol dibenzoate.
13. A method of reducing eye irritation of a liquid composition comprising at least one active ingredient and at least one emulsifier, the method comprising including in the composition at least one dipropylene/diethylene glycol dibenzoate in the composition.
14. The method according to claim 13, wherein the active ingredient comprises a compound selected from clomazone, a pyrethroid ester, a cyclohexime oxime, a benzoylphenylurea chitin synthesis inhibitor, and an avermectin.
15. The method according to claim 14, wherein the active ingredient comprises a compound selected from bifenthrin, pyriproxyfen, clethodim, clomazone, abamectin and lufenuron.
16. The method according to any of claims 13 to 15, wherein the emulsifier comprises a non-ionic emulsifier.
17. The method according to claim 16, wherein the non-ionic emulsifier is selected from an alcohol alkoxylate, an alkylphenol ethoxylate, an alkylpolysaccharide, an amine ethoxylate, a castor oil ethoxylate, a sorbitan fatty acid ester ethoxylate and a polyoxyethylene fatty acid.
18. The method according to any of claims 13 to 17, wherein the emulsifier comprises an ionic emulsifier.
19. The method according to claim 18, wherein the ionic emulsifier is selected from an amine alkylbenzenesulfonate, an ammonium dodecylbenzene sulfonate, a calcium alkylsulphonate and a calcium alkylbenzenesulfonate.
20. The method according to any of claims 13 to 19, wherein the emulsifier comprises a cationic emulsifier.
21. The method according to claim 20, wherein the cationic emulsifier is selected from polyoxyethylene quaternary and polyoxyethylene tallow ethylmonium ethosulfate, stearyltrimethylammonium chloride and benzyl bis(2-chloroethyl)ethylammonium bromide.
22. The method according to any of claims 13 to 21, wherein the at least one dipropylene/diethylene glycol dibenzoate is diethylene glycol dibenzoate or dipropylene glycol dibenzoate.
23. The method according to any of claims 13 to 22, wherein the at least one dipropylene/diethylene glycol dibenzoate comprises a mixture of diethylene glycol dibenzoate and dipropylene glycol dibenzoate.
24. The method according to any of claims 13 to 23, wherein the composition is a liquid concentrate.
25. The method according to claim 24, wherein the composition is an emulsifiable concentrate (EC) formulation.
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| GB1906116.7A GB2571647B (en) | 2014-12-02 | 2014-12-02 | The use of dipropylene/diethylene glycol dibenzoate to reduce eye irritation |
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| WO2010064266A1 (en) * | 2008-12-03 | 2010-06-10 | Lamberti S.P.A. | Liquid composition for pesticide concentrates |
| WO2012022253A1 (en) * | 2010-08-17 | 2012-02-23 | Rotam Agrochem International Co., Ltd | Herbicidal compositions |
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| WO2010064266A1 (en) * | 2008-12-03 | 2010-06-10 | Lamberti S.P.A. | Liquid composition for pesticide concentrates |
| WO2012022253A1 (en) * | 2010-08-17 | 2012-02-23 | Rotam Agrochem International Co., Ltd | Herbicidal compositions |
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