OA16303A - Formulations. - Google Patents
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- OA16303A OA16303A OA1201300025 OA16303A OA 16303 A OA16303 A OA 16303A OA 1201300025 OA1201300025 OA 1201300025 OA 16303 A OA16303 A OA 16303A
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- OA
- OAPI
- Prior art keywords
- optionally substituted
- formulation
- formula
- compound
- alkyl
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- 239000000203 mixture Substances 0.000 title claims abstract description 28
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- 238000009472 formulation Methods 0.000 claims abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims abstract description 16
- 125000004432 carbon atoms Chemical group C* 0.000 claims abstract description 12
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 13
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 12
- -1 hexafluoroisopropyl Chemical group 0.000 claims description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000003944 tolyl group Chemical group 0.000 claims description 4
- 238000003972 agrochemical formulation Methods 0.000 claims description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- BPZSYCZIITTYBL-YJYMSZOUSA-N Formoterol Chemical compound C1=CC(OC)=CC=C1C[C@@H](C)NC[C@H](O)C1=CC=C(O)C(NC=O)=C1 BPZSYCZIITTYBL-YJYMSZOUSA-N 0.000 claims description 2
- VDHAWDNDOKGFTD-MRXNPFEDSA-N cinacalcet Chemical compound N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCCC1=CC=CC(C(F)(F)F)=C1 VDHAWDNDOKGFTD-MRXNPFEDSA-N 0.000 claims description 2
- 229960003315 cinacalcet Drugs 0.000 claims description 2
- 229960002848 formoterol Drugs 0.000 claims description 2
- 239000004495 emulsifiable concentrate Substances 0.000 claims 1
- OEUAEFQARUZYLW-UHFFFAOYSA-N prop-1-en-2-olate Chemical group [CH2+]C([O-])=C OEUAEFQARUZYLW-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 45
- 239000002671 adjuvant Substances 0.000 abstract description 9
- 230000000240 adjuvant Effects 0.000 abstract description 9
- 238000004519 manufacturing process Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- JBSLOWBPDRZSMB-BQYQJAHWSA-N dibutyl (E)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C\C(=O)OCCCC JBSLOWBPDRZSMB-BQYQJAHWSA-N 0.000 description 14
- 241000196324 Embryophyta Species 0.000 description 12
- 239000000575 pesticide Substances 0.000 description 11
- 125000005843 halogen group Chemical group 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Substances C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 6
- XTDZGXBTXBEZDN-UHFFFAOYSA-N 3-(difluoromethyl)-N-(9-isopropyl-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl)-1-methylpyrazole-4-carboxamide Chemical compound CC(C)C1C2CCC1C1=C2C=CC=C1NC(=O)C1=CN(C)N=C1C(F)F XTDZGXBTXBEZDN-UHFFFAOYSA-N 0.000 description 5
- 239000005799 Isopyrazam Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000003905 agrochemical Substances 0.000 description 5
- 230000002363 herbicidal Effects 0.000 description 5
- 239000004009 herbicide Substances 0.000 description 5
- KWOLFJPFCHCOCG-UHFFFAOYSA-N methylphenylketone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- NNBZCPXTIHJBJL-UHFFFAOYSA-N Decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 235000007320 Avena fatua Nutrition 0.000 description 3
- 241000209764 Avena fatua Species 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- 235000005773 Setaria viridis Nutrition 0.000 description 3
- 240000003461 Setaria viridis Species 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 230000002708 enhancing Effects 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N fumaric acid Chemical class OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 235000002248 green bristle grass Nutrition 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- AIAYSXFWIUNXRC-PHIMTYICSA-N (1R,5S)-3-[hydroxy-[2-(2-methoxyethoxymethyl)-6-(trifluoromethyl)pyridin-3-yl]methylidene]bicyclo[3.2.1]octane-2,4-dione Chemical compound COCCOCC1=NC(C(F)(F)F)=CC=C1C(O)=C1C(=O)[C@@H](C2)CC[C@@H]2C1=O AIAYSXFWIUNXRC-PHIMTYICSA-N 0.000 description 2
- UFNOUKDBUJZYDE-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC(Cl)=CC=1)C(C)C1CC1 UFNOUKDBUJZYDE-UHFFFAOYSA-N 0.000 description 2
- 239000005757 Cyproconazole Substances 0.000 description 2
- 239000005760 Difenoconazole Substances 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- KWKXNDCHNDYVRT-UHFFFAOYSA-N Dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 2
- 239000005578 Mesotrione Substances 0.000 description 2
- KPUREKXXPHOJQT-UHFFFAOYSA-N Mesotrione Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O KPUREKXXPHOJQT-UHFFFAOYSA-N 0.000 description 2
- 239000005597 Pinoxaden Substances 0.000 description 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N Triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
- 229960002622 Triacetin Drugs 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- BQYJATMQXGBDHF-UHFFFAOYSA-N difenoconazole Chemical compound O1C(C)COC1(C=1C(=CC(OC=2C=CC(Cl)=CC=2)=CC=1)Cl)CN1N=CN=C1 BQYJATMQXGBDHF-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 229940093499 ethyl acetate Drugs 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 235000013773 glyceryl triacetate Nutrition 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- MGOHCFMYLBAPRN-UHFFFAOYSA-N pinoxaden Chemical compound CCC1=CC(C)=CC(CC)=C1C(C1=O)=C(OC(=O)C(C)(C)C)N2N1CCOCC2 MGOHCFMYLBAPRN-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N (+-)-(RS)-limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 1
- 125000006592 (C2-C3) alkenyl group Chemical group 0.000 description 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
- SASYHUDIOGGZCN-ONEGZZNKSA-L (E)-2-ethylbut-2-enedioate Chemical compound CC\C(C([O-])=O)=C/C([O-])=O SASYHUDIOGGZCN-ONEGZZNKSA-L 0.000 description 1
- XLYMOEINVGRTEX-ONEGZZNKSA-M (E)-4-ethoxy-4-oxobut-2-enoate Chemical class CCOC(=O)\C=C\C([O-])=O XLYMOEINVGRTEX-ONEGZZNKSA-M 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N (E)-but-2-enedioate;hydron Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 102100017923 ACOT12 Human genes 0.000 description 1
- 101710008266 ACOT12 Proteins 0.000 description 1
- 241000743985 Alopecurus Species 0.000 description 1
- 241000482638 Amaranthus tuberculatus Species 0.000 description 1
- 239000005730 Azoxystrobin Substances 0.000 description 1
- WFDXOXNFNRHQEC-GHRIWEEISA-N Azoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1OC1=CC(OC=2C(=CC=CC=2)C#N)=NC=N1 WFDXOXNFNRHQEC-GHRIWEEISA-N 0.000 description 1
- TXUOQDYWEDWXGO-UHFFFAOYSA-N CCCCCCCCCCCCC1=CC=CC=C1.CCCCCCCCCCCCC1=CC=CC=C1 Chemical compound CCCCCCCCCCCCC1=CC=CC=C1.CCCCCCCCCCCCC1=CC=CC=C1 TXUOQDYWEDWXGO-UHFFFAOYSA-N 0.000 description 1
- 101700046984 CDK20 Proteins 0.000 description 1
- 239000005747 Chlorothalonil Substances 0.000 description 1
- CRQQGFGUEAVUIL-UHFFFAOYSA-N Chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 1
- 241000238578 Daphnia Species 0.000 description 1
- 235000017896 Digitaria Nutrition 0.000 description 1
- 241001303487 Digitaria <clam> Species 0.000 description 1
- 241001289540 Fallopia convolvulus Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 206010062080 Pigmentation disease Diseases 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- 241000972221 Urochloa decumbens Species 0.000 description 1
- 230000000895 acaricidal Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- WAROTACXSPDFIV-MDZDMXLPSA-N bis(2-methylpentyl) (E)-but-2-enedioate Chemical compound CCCC(C)COC(=O)\C=C\C(=O)OCC(C)CCC WAROTACXSPDFIV-MDZDMXLPSA-N 0.000 description 1
- PUMKVEQREANDNI-BQYQJAHWSA-N bis(3-methylpentyl) (E)-but-2-enedioate Chemical compound CCC(C)CCOC(=O)\C=C\C(=O)OCCC(C)CC PUMKVEQREANDNI-BQYQJAHWSA-N 0.000 description 1
- AUUKMDXZUNSGGI-MDZDMXLPSA-N bis(4-methylpentyl) (E)-but-2-enedioate Chemical compound CC(C)CCCOC(=O)\C=C\C(=O)OCCCC(C)C AUUKMDXZUNSGGI-MDZDMXLPSA-N 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- DJOLQBLYDDQTSY-MDZDMXLPSA-N dipentan-2-yl (E)-but-2-enedioate Chemical compound CCCC(C)OC(=O)\C=C\C(=O)OC(C)CCC DJOLQBLYDDQTSY-MDZDMXLPSA-N 0.000 description 1
- FNMTVMWFISHPEV-AATRIKPKSA-N dipropan-2-yl (E)-but-2-enedioate Chemical compound CC(C)OC(=O)\C=C\C(=O)OC(C)C FNMTVMWFISHPEV-AATRIKPKSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- YYLWXDIGYFPUSK-ONEGZZNKSA-N ethyl (E)-4-chloro-4-oxobut-2-enoate Chemical compound CCOC(=O)\C=C\C(Cl)=O YYLWXDIGYFPUSK-ONEGZZNKSA-N 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000001087 glyceryl triacetate Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 239000008079 hexane Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 230000000749 insecticidal Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229930007650 limonene Natural products 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000019612 pigmentation Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Abstract
This invention relates to a formulation comprising a compound of formula (I) where R1 and R2 are each independently hydrogen, optionally substituted C1-18 alkyl, optionally substituted C1-18 alkenyl, optionally substituted C38cycloalkyl, optionally substituted C3-8cycloalkenyl or optionally substituted aryl; provided that the total number of carbon atoms in R1 and R2 is an integer from 5 to 40 inclusive; the use of a compound of formula (I) (i) as an adjuvant provided that the total number of carbon atoms in R1 and R2 is an integer from 5 to 40 inclusive; and (ii) as a solvent provided that the total number of carbon atoms in R1 and R2 is an integer from 5 to 20 inclusive; to certain novel compounds of formula (I) and to a process for preparing those novel compounds.
Description
This invention relates to the use of certain ftimarate compounds as solvents, especially in formulations, particularly in agrochemicai formulations and in environmentally frîendly formulations; and to certain novel compounds. The solvents of the présent invention are found to be particularly effective at forming stable émulsions in water.
Nowadays, the Formulation Chemist is required to address a number of environmental criteria when developing new formulations. Ideally, a suitable solvent will display many or ali of the following properties: a low water solubility; an excellent dissolving power for pesticides or other organic molécules; made from plant or animal rcncwable rcsources; low skin irritation; low ccotoxicity, for example to daphnia; low volatile organic content; and a high flash point. The compounds of the présent invention each display ail or many of these properties, in particular they form stable émulsions in water; the compounds may be used effectively as solvents.
Accordingly, the présent invention provides the use of a cornpound of formula (I) as a solvent
O where R1 and R2 are each independently hydrogen, optionally substituted [i.e. substituted or unsubstîtuted] Cj.]g alkyl, optionally substituted [i.e. substituted or unsubstîtuted] Cms alkenyl, optionally substituted [i.e. substituted or unsubstîtuted] C3_8 cycloalkyl, optionally substituted [i.e. substituted or unsubstîtuted] Ci.g cycloalkenyl or optionally substituted [i.e. substituted or unsubstîtuted] aryl; provided that the total number of carbon atoms in R1 and R2 is an integer from 5 to 40 inclusive, suitably from 5 to 20 inclusive. The expression “the total number of carbon atoms in R1 and R2 is an integer from 5 to 20 inclusive” means, for example, that if R1 contains 2 carbon atoms, then R2 may contain from 3 to 18 carbon atoms.
The présent invention also relates to fumarates which can act as an adjuvant to enhance signifîcantly the biological performance of a pesticide.
-2Accordingly, the présent invention provides the use as an adjuvant of a compound of formula (I) as defined above; suitably it provides the use as an adjuvant of a compound of formula (I)
O (I) where R1 and R2 are each independently hydrogen, optionally substituted Cms alkyl, optionally substituted Cms alkenyl, optionally substituted C3.s cycloalkyl or optionally substituted C3_s cycloalkenyl; provided that the total number of carbon atoms in R1 and R2 is an integer from 5 to 40 inclusive [suitably from 5 to 20 inclusive].
Alkyl groups and moieties are straight or branched chains. Examples are methyl, ethyl, iso-propyl, n-propyl, n-butyl, sec-butyl, te/7-butyl, rt-amyl, iso-amyl [3-mcthylbutyl], n-pentyl and n-nexyl.
Alkenyl groups and moieties may be in the form of straight or branched chains and, where appropriate, may be of either the (E)- or (//-configuration. Examples are vinyl and allyl.
Cycloalkyl includes cyclyopropyl, cyclobutyl and cyclopentyl.
Cycloalkenyl includes cyclobutenyl and cyclopentenyl.
Aryl includes phenyl. Suitably aryl is phenyl.
Optional substituents on alkyl are selected from hydroxy, =0, halo, -NH2, -C(=O)NH2, -C(=O)OH, -O(Ci-3)alkyl and C1-3 cycloalkyl; suitably they arc selected from hydroxyl and halo.
Optional substituents on alkenyl are selected from hydroxy, =O, halo, -NH2, -C(=0)NH2, -C(=O)OH, -O(Ci.3)alkyl and C1-3 cycloalkyl; suitably they are selected from hydroxyl and halo.
Optional substituents on cycloalkyl are selected from hydroxy, =0, halo and
Ci-3 alkyl; suitably they are selected from hydroxyl and halo.
Optional substituents on cycloalkenyl are selected from hydroxy, =0, halo and
C1.3 alkyl; suitably they are selected from hydroxyl and halo.
-3Optional substituents on aryl arc independently selected from Ci.3 alkyL, halo, cyano, Cj.3 haloalkyl, Cj.3 alkoxy, Ci-3 haloalkoxy, C2-3 alkenyl, Cj-3 alkoxyCi.3 alkylene, C(.j alkoxyC(=O)~ and C].3 alkylsulphonyl; suitably Cj.2 alkyl; more suitably methyl.
Suitably optionally substituted aryl is suitably optionally substituted [i.e. substituted or unsubstituted] phenyl or optionally substituted [i.e. substituted or unsubstituted] tolyl; more suitably phenyl or tolyl; preferably phenyl. In one aspect it is optionally substituted phenyl.
Suitably halo îs chloro, fluro or bromo; more suitably chloro or fluoro.
Suitably R1 is hydrogen or Cms alkyl optionally substituted by one, two or three hydroxyl groups.
Suitably R2 is C3.18 alkyl optionally substituted by one, two or three hydroxyl groups.
Suitably R1 is hydrogen, methyl, ethyl, linear or branched propyl, or linear or branched butyl ; more suitably R1 is either propyl or butyl where R2 is either propyl or butyl
Suitably R2 is propyl or butyl when R1 is butyl.
Suitably R1 is butyl when R2 is also butyl; more suitably, both are n-butyl.
In one aspect of the présent invention, suitably R1 is hydrogen or Ci_2 alkyl and R2 is substituted or unsubstituted phenyl; suitably R1 is ethyl; suitably R2 is substituted phenyl.
The présent invention encompasses ali isomers, or mixtures of isomers, of compounds of formula (I) and also encompasses mixtures of two or more different compounds of formula (I).
The sélection of solvents for an (agricultural) émulsion concentrate or water-dispersed émulsion formulation is complicated. Often there is a requirement for two different solvents. A solvent which has an aqueous solubility of at least 0.1 % w/w [at the relevant température] may dissolve apprecîably in an agrochemical spray tank full of water, under normal dilution or dispersion conditions [for example, at températures of from just above freezing to 35°C], Such a solvent will not form stable émulsions in water when formulated with surfactants however it may be an effective solvent for dissolving pesticides. Such a solvent is normally also formulated with an oil of much lower water solubility. Solvents which hâve aqueous solubility values below 0.1 %w/w [at the relevant température] are used along with a solvent with the above higher aqueous solubility in order to be able to préparé stable émulsions. The solvent with the low water solubility is normally a poor solvent for dissolving pesticides. The surprising finding about the fumarate solvents ofthe
-4présent invention is that they hâve a low water solubility yet they arc also good solvents for pesticides. This fact is amply displayed în the data given in the Examples.
Table ï provides structures of suitable compounds of formula (I).
Table 1
| Compound Number | RJ | R2 |
| 1.1 | CH3CH2CH2 | ch3ch2ch2 |
| 1.2 | (CH3)2CH | (CH3)2CH |
| 1.3 | CH3CH2CH2CH2 | ch3ch2ch2ch2 |
| 1.4 | (CH3)2CHCH2 | (CH3)2CHCH2 |
| 1.5 | CH3CH2CH2CH2CH2 | CH3CH2CH2CH2CH2 |
| 1.6 | CH3CH2CH2CH(OH)CH2 | CH3CH2CH2CH(OH)CH2 |
| 1.7 | CH3CH(CH3)CH2CH; | CH3CH(CH3)CH2CH2 |
| 1.8 | ch3ch2ch2ch2ch2 ch2 | CH3CH2CH2CH2CH2 ch2 |
| 1.9 | CH3CH2CH2CH(CH3)C(OH) | CH3CH2CH2CH(CH3)C(OH) |
| 1.10 | CH3CH2CH(CH3)CH2C(OH) | CH3CH2CH(CH3)CH2C(OH) |
| 1.11 | CH3CH(CH3)CH2CH2C(OH) | CH3CH(CH3) CH2CH2C(OH) |
| 1.12 | hoch2ch2ch2 | ch3ch2ch2 |
| 1.13 | cich2ch2ch2 | ch3ch2ch2 |
| 1.14 | ch2=chch2 | ch3ch2ch2 |
| 1.15 | ch3ch2ch2 | ch3ch2 |
| 1.16 | ch2=chch2 | CHjCH2 |
| 1.17 | (ch3)2ch | ch3ch2 |
| 1.18 | CIEC-CIb | (CH3)2CH |
| 1.19 | CH3CHCH2C1 | (CH3)2CH |
| 1.2 | ch3ch2ch2ch2 | ch3 |
| 1.21 | ch3ch2ch2ch2 | ch3ch2 |
| 1.22 | ch2=chch2ch2 | ch3ch2ch2ch2 |
| 1.23 | cich2ch2ch2ch2 | ch3ch2ch2ch2 |
| 1.24 | (CH3)2CHCH2 | ch3 |
| 1.25 | (CH3)2CHCH2 | ch3ch2 |
| 1.26 | CH3CH(=CH2)CH2 | (CH3)2CHCH2 |
| 1.27 | CH3C(=CH2)CH2 | (CH3)2CHCH2 |
| 1.28 | C1CH2CH(CH3)CH2 | (CH3)2CHCH2 |
| 1.29 | CH3CH2CH2CH2CH2 | H |
| 1.30 | ch3ch2ch2ch2ch2 | ch3 |
| 1.31 | CH3CH2CH2CH2CH2 | ch3ch2 |
| 1.32 | ch3ch2ch2ch2ch2 | ch3ch2ch2 |
| 1.33 | ch3ch2ch2ch2ch2 | ch3ch2ch2ch2 |
| 1.34 | ch2=chch2ch2ch2 | ch3 |
| 1.35 | CH3CH2CH2CH2CH2CH2 | H |
| 1.36 | CH3CH2CH2CH2CH2CH2 | ch3ch2 |
| 1.37 | CH2=CHCH2CH2CH2CH2 | ch3ch2ch2 |
| 1.38 | ch3ch=chch2ch2ch2 | ch3 |
| 1.39 | cich2ch2ch2ch2ch2ch2 | ch3ch2 |
| 1.40 | CH3(CH2)7CH=CH(CH2)s | ch3 |
| 1.41 | CH3(CH2)7CH=CH(CH2)8 | ch3ch2ch2ch2 |
| 1.42 | CH3(CH2)7CH=CH(CH2)s | CH3(CH2)7CH=CH(CH2)8 |
| 1.43 | Phenyl | H |
| 1.44 | Phenyl | ch3 |
| 1.45 | Phenyl | Phenyl |
Suîtably the invention provides the use of a compound of formula (I) in an agrochemical formulation.
Many, but not ail, of the compounds used by the présent invention are novel.
Therefore in a further aspect, the présent invention provides a compound of formula (I) as defined above provided that when R1 is CH3CH2CH2, (CH3)3C, (CHfhCH, CH3CH2CH2CH2, (CH3)2CHCH2, CH3CH2CH2CH2CH2, CH3CH2CH2CH(OH)CH2, CH3CH(CH3)CH2CH2, CH3CH2CH2CH2CH2 CH2j CH3CH2CH2CH(CH3)C(OH), CH3CH2CH(CH3)CH2C(OH),CH3CH2CH2CH2CH2(CH2CH3)CH2,hexafluoroisopropyl, hydroxyîsopropyl, cyclohexyl, cinacalcet, formoterol, HOCH2CH2CH2SO3, CH3CHOHCH2SO3, CH3CH(C(CH3)3)CH2CH(CH3)CH2 or CH3CH(CH3)CH2CH2C(OH), then R2 is not the same as R1; when R1 is CH3CH(CH3) then R2 is not perfluorohexylethyl, perfluorooctylethyl, (CH3)3C, CH3CH(CH3)CH2 or cyclohexyl; when R1 is cyclohexyl then R2 is not CH3CH(CH3)CH2 or (CH3)3C; and when R1 is hydrogen then R2 is not stearyl.
The compounds of the invention may be used in a variety of applications (including agrochemical formulations), particularly as solvents. These solvents may be used with a wide variety of materials, including herbicides, fongicides, acaricides, nematicides, insecticides and plant growth regulators.
t .
-7The compounds of the invention may be used to formulate solutions of a varicty of materials, including agrochemicals, which may be formulated as émulsion or dispersion concentrâtes, émulsions in water or oil, microencapsulated formulations, aérosol sprays or fogging formulations; and these may be further formulated into granular materials or powders, for example for dry application or as water-dispersible formulations. Any solutions so formed may also be used directly on soil or plants or in other non-agrochemical applications.
Examples of suitable applications include paper making, water treatment, forestry applications, public health treatments, use în municipal pools and other water courses, in applications ncar rivers, lakcs, réservoirs or scas and in applications where release to the atmosphère has to bc minîmised or controlled and where damage to the atmosphère is not désirable. Examples include use in exterior and interior paints, coatings, vamishes, waxes or other protectant layers or opacificrs, colourants or screens; in dyeing, pigmentation or the use of inks; in cleaning products designed for the home, garden or industrial applications; and in soap or detergent applications for industrial, home or environmental usage. The compounds of the présent invention may also be used in shampoos, household detergency and in household cleaners [for example oven cleaners and surface cleaners].
The compounds of the présent invention hâve exceptional dissolving power for a wide varicty of agrochemicals, pharmaceuticals and other commcrcially valuable compounds, plus the dissolving power also extends to dissolution of dirt, grease or waxes.
The invention is illustrated by the following Examples in which: g = grammes °C = degrees centigrade
N/A = not available
Unless otherwise stated, each concentration is expressed as percentage by weight.
«
EXAMPLE 1
This Example demonstrates the low water solubility of (E)-but-2-enedioic acid di n-butyl ester. Typîcally, solvents which havc aqueous solubilitics of about (or at least) 0.1 % w/w [at the relevant température] can dissolve appreciably in agrochemîcal spray tanks under normal dilution conditions [for example, températures of from just above freezing to 35°C). These solvents do not form stable émulsions in water when used by themselves. Solvents such as acetophenone are normally formulated with an oil of much lower water solubility. For example, solvents which hâve aqueous solubility values typîcally below
-80. l%w/w [at the relevant température] arc suitable for preparing émulsions. Table 2 provides water solubilities for a number of solvents at 25°C. Saturated solutions of each solvent in deionised water were prepared by leaving excess solvent in contact with water for a period of at least two weeks. After this time a sample of the water was analysed chromatographically to détermine the concentration of solvent présent.
Table 2
| Solvent | % water solubility [by weight at 25°C] |
| Dodecylbenzene ( 1 -phenyldodecane) | 0.000026 |
| Dicaprylyl carbonate (CetiolIM CC) | 0.000039 |
| Exxsol1M D-80 (Dodecane) | 0.00089 |
| (E)-But-2-enedioic acid dibutyl ester | 0.04 |
| Jeffsoi151 AG-1723 | 0.04 |
| Dipentene (limoncne) | 0.098 |
| Tetralin1M (tetrahydronap hthalene) | 0.18 |
| ‘Norpar1''1 15 | 0.4 |
| Decalin (decahydronaphthalene) | 0.7 |
| Genagen1M 4166 (dimethyl heptamide) | 0.7 |
| Dicthyl fumaratc | 0.8 |
| Acetophenone (methyl phenyl ketone) | 0.9 |
| Benzyl alcohol, benzene méthanol | 4.4 |
| Triacetin (glycerol triacetate) | 7.7 |
EXAMPLE 2
In this Example several solvents of the présent invention were used to dissolve lû isopyrazam. The results show that these are effective solvents for this agrochemical. A glass vial was approximately one eighth filled with an active ingrédient and then solvent was added until the vial was approximately one third full. The résultant sample was mixed with a Whirlimixer™ and was then stored at 25°C. The sample was checked every few days; if there was no solid active ingrédient présent then additional active ingrédient was added; if there was no liquid remaining then additional solvent was added. This procedure was repeated until the sample had equilibrated for 4 weeks following the final addition of either active ingrédient or solvent. The supematant liquid layer was then analysed by gas θ'
-9chromotography for active ingrédient concentration; the solubilitics of isopyrazam în several solvents are given in Table 3:
Table 3
| Solvent | Isopyrazam % w/w |
| (E)-But-2-enedioic acid dibutyl ester | 5.0 |
| (E)-But-2-enedioîc acid diisopropyl ester | 6.0 |
| (E)-But-2-enedioic acid dîisobutyl ester | 4.8 |
| (E)-But-2-cncdioic acid dipentyl ester | 4.6 |
| (E)-But-2-enedioic acid bis(l-methyl-butyl) ester | 3.5 |
| (E)-But-2-cncdioic acid bîs(3-methyl-butyl) ester | 3.7 |
| (E)-But-2-enedîoic acid dîhexyl ester | 3.7 |
| (E)-But-2-enedioic acid bis(2-methyl-pentyl) ester | 3.0 |
| (E)-But-2-enedioic acid bis(3-methyl-pentyl) ester | 3.1 |
| (E)-But-2-enedioic acid bis(4-methyl-pentyl) ester | 2.3 |
EXAMPLE 3
This Example shows that the solvents of the présent invention are particularly effective at solubilising pesticides. Tables 4a and 4b show the solubility of the pesticides azoxystrobin, difenoconazole, isopyrazam, cyproconazole, chlorothalonîl and bicyclopyrone in the solvent (E)-but-2-enedioic acid dibutyl ester. For comparison the solubilities in a sériés of commonly used, low water solubility solvents are also tabulated. The data show that in most cases the (E)-but-2-enedioic acid dibutyl ester was a more effective solvent. Solubilities are quoted as pcrcentage w/w at 20°C.
- 10Table 4a
| Solvent | Azoxystrobîn | Cyproconazole | Difenoconazole |
| Dîpentene | 0.14 | 1 | 5.9 |
| Norpar1 M 15 | 0.16 | 0.1 | 0.4 |
| Decalin | 0.03 | 0.4 | 1.8 |
| Exxsol1M D-80 | 0.13 | 0.5 | 0.9 |
| JeffsoljM AG-1723 | 0 | 0.9 | N/A |
| Dodecylbenzene | 0 | 0.9 | N/A |
| (E)-But-2-enedio ic acid dibutyl ester | 1.4 | 6.5 | 18 |
| Dicaprylyl carbonate | 0 | 2.6 | N/A |
| Tetralin | 1.85 | 5.2 | N/A |
Table 4b
| Solvent | Chlorothalonil | Bicyclopyrone | Isopyrazam |
| Dîpentene | 0.18 | 7.4 | 0.8 |
| Norpar1 M 15 | N/A | 0.3 | 0.3 |
| Decalin | N/A | 1.8 | 0.3 |
| Exxsol1M D-80 | N/A | 0.97 | 0.3 |
| Jeffsollk AG-1723 | N/A | N/A | 0.39 |
| Dodecylbenzene | N/A | N/A | 0.6 |
| (E)-But-2-enedioic acid dibutyl ester | 0.6 | 16 | 5.0 |
| Dicaprylyl carbonate | N/A | N/A | 1.9 |
| Tetralin | N/A | N/A | 2.6 |
EXAMPLE 4
This Example shows that (E)-but-2-enedioic acid dibutyl ester may act as an adjuvant to enhance significantly the biological performance of a pesticide. The weed species Setaria Viridis (SETVI), Lolîum Perenne (LOLPE), Avena Fatua (AVEFA) and Alopecurus
Myosuroides (ALOMY) were grown under glass house conditions and sprayed with the
- u herbicide pinoxaden at a rate of 7.5 grams of pesticide per hectare. Weeds were treated with pinoxaden in the absence of (E)-but-2-enedioic acid dibutyl ester (as a control) and also with (E)-but-2-enedioîc acid dibutyl ester added to the spray-tank at a concentration of 0.2% by volume. After both 14 and 21 days the efficacy of the herbicide was assessed based on the percentage of the weeds that had been killed. Three replaçâtes were used in ail cases. The average percentage of weeds killed is quoted in Table 5 for each weed species either with the adjuvant or without (control). Results hâve been averaged across three replicates. The standard déviation for each resuit is shown in brackets after the resuit. The results in Table 5 show that at a confidence level of 95% the solvent-containing System was found to be more cfficacious than the adjuvant-free formulation.
Table 5
| Adjuvant | Days after application | ALOMY | AVEFA | LOLPE | SETVI |
| (E)-But-2-cnedioic acid dibutyl ester | 14 | 20(17.3) | 20(10) | 13.3(5.8) | 20(0) |
| None | 14 | 1.7(2.9) | 0(0) | 6.7(5.8) | 0(0) |
| (E)-But-2-enedioic acid dibutyl ester | 21 | 33.3(15.3) | 16.7(5.8) | 6.7(5.8) | 20(10) |
| None | 21 | 0(0) | 0(0) | 0(0) | 0(0) |
EXAMPLE 5
This Example shows that (E)-but-2-enedioic acid dibutyl ester can act as an adjuvant to enhance significantly the biological performance of a pesticide. The weed species Polygonum Convolvulus, Digitaria Sanguînalis, Brachiaria Decumbens and Amaranthus Tuberculatus were grown under glass house conditions and sprayed with the herbicide mesotrione at rate of 45 grams of pesticide per hectare. Weeds were treated with the mesotrione in the absence of (E)-but-2-enedioic acid dibutyl ester (as a control) and also with (E)-but-2-cncdioic acid dibutyl ester added to the spray-tank at a concentration of 0.2%v/v. After 14 and 21 days the efficacy of the herbicide was assessed based on the percentage of the weeds that had been killed. Three replicates were used in ail cases. The performance of the solvent was assessed by averaging the three replicates at each time period and for each weed. The standard déviation for each resuit is shown in brackets after the average percentage weed kill. The results in Table 6 show' that at a confidence level of 95% the
-12solvcnt-containing System was found to be more cfficacious than the adjuvant-free formulation.
Table 6
| Adjuvant | Days after application | AMATU | BRADE | DIGSA | POLCO |
| (E)-But-2-enedioic acid dibutyl ester | 21 | 94(3.6) | 40(0) | 41.7(7.6) | 80(10) |
| Noue | 21 | 85(5) | 16.7(11.5) | W(0) | 76.7(5.8) |
| (E)-But-2-enedioic acid dibutyl ester | 14 | 76.7(5.8) | 43.3(5.8) | 36.7(2.9) | 80(10) |
| None | 14 | 63.3(5.8) | 20(10) | 13.3(5.8) | 66.7(15.3) |
EXAMPLE 6
This Example describes how certain ethyl fumarates according to the présent invention were 5 prepared; for each of these fiimarates, R1 is ethyl; and R2 is a substituted phenyl [derived from the corresponding phcnol]. To a solution of the relevant phénol (3.3 mmol) in dichloromethane (2.0ml) at 0°C was added a solution of triethylamîne (0.47ml) in dichloromethane (2.0ml) followed by a solution of ethyl fumaryl chloride (500mg) in dichloromethane (2.0ml). The réaction mixture was stirred at 0°C until completion of the réaction and then the solvent was evaporated. The residue was partitioned between 2M K2CO3 and ethylacetate, the organics were evaporated to dryness and the crude product was purified by flash chromatography on 10g silica cartridges using ethylacetate/hexane as eulent. Confirmation that the required ethyl fumarate had been prepared was made by NMR spectroscopy (*H NMR (400 MHz, CDCh )}. The compounds tabulated, with their NMR data, in Table 7 were cach prepared in this manner. In the Table, conventional tcrminology is used; for example, m=multiplet; s=singlet; d=doublet; dd=double doublet; t=triplet; q= quartet. Each compound of Table 7 is a compound of formula (I) where R1 is ethyl and R2 is as defined in Table 7.
Table 7
| Compound Number | R2 | 'H NMR (400 MHz, CDC13 ) |
| 7.1 | 7.20-7.15 (4H, m), 7.05 (2H, s), 4.30 (2H, q), 2.50 (2H, t), 1.651.55 (2H, m), 1.35 (3H, t), 0.95 (3H,t) | |
| 7.2 | A | 7.65 (IH, d), 7.35 (IH, dd), 7.20- 7.10 (2H, m), 7.10 (2H, s), 4.30 (2H, q), 1.35 (3H, t) |
| 7.3 | F | 7.70 (IH, dd), 7.20-7.10 (2H, m), 7.05 (2H, 2 x s), 4.30 (2H, q), 1.35 (3H,t) |
| 7.4 | AC F | 7.60 (IH, d), 7.50 (IH, d), 7.50 (IH, s), 7.10 (2H, s), 4.30 (2H, q), 1.35 (3H, t) |
| 7.5 | —O « | 7.35 (IH, d), 7.05 (2H, s), 6.80 (IH, d), 6.75 (IH, s), 4.30 (2H, q), 3.80 (3H, s), 1.35 (3H, t) |
| 7.6 | LL | 7.05 (2H, s), 6.80-6.70 (3H, m), 4.30 (2H, q), 1.35 (3H, t) |
| 7.7 | AV | 7.05 (2H, s), 7.05-7.00 (IH, m), 6.75-6.60 (2H, m), 4.30 (2H, q), 3.80 (3H, s), 1.35 (3H, t) |
| 7.8 | Cl c. | 7.35 (IH, dd), 7.25 (IH, d), 7.20 (IH, s), 7.05 (IH, d), 7.05 (2H, s), 4.30 (2H, q), 1.35 (3H, t) |
| 7.9 | ο \ | 7.10 (2H,d), 7.05 (2Η, s), 6.90 (2Η, d), 4.30 (2Η, q), 3.80 (3H, s), 1.35 (3H, t) |
| 7.10 | Ά | 7.00 (2H, s), 6.80 (2H, d), 6.60 (IH, S),4.3O(2H, q), 3.80 (3H, s), 1.35 (3H, t) |
| 7.11 | V. CI | 7.75 (IH, s), 7.60 (IH, d), 7.25 (IH, d), 7.10 (2H, s). 4.35 (2H, q), 1.35 (3H, t) |
| 7.12 | κ | 7.50 (IH, s), 7.30 (IH, m), 7.15 (IH, d), 7.05 (2H, s), 4.30 (2H, q), 1.35 (3H, t) |
| 7.13 | F | 7.55 (2H,d), 7.45 (IH, s), 7.40- 7.30 (IH, m), 7.05 (2H, s), 4.30 (2H, q), 1.35 (3H, t) |
| 7.14 | Λ Ο | 8.00 (2H, d), 7.40 (2H, d), 7.05 (2H, s), 4.30 (2H, q), 3.10 (3H, s), 1.35 (3H, t) |
| 7.15 | 7.30-7.20 (3H, m), 7.10 (IH, d), 7.05 (X s), 5.95-5.85 (IH, m), 5.10-5.00 (2H, m), 4.30 (2H, q), 3.30 (2H, d), 1.35 (3H, t) | |
| 7.16 | “IX | 7.25 (IH, s), 7.20 (IH, d), 7.05 (2H, s), 7.00 (IH, d), 4.30 (2H, q), 2.15 (3H, s), 1.35 (3H, t) |
| 7.17 | C F— F | Æ — F | 7.45 (IH, dd), 7.15-7.10 (2H, m), 7.10 (IH, s), 7.05 (2H, s), 4.30 (2H, q), 1.35 (3H, t) |
| 7.18 | |||
| CI | Cl | 7,40 (IH, d), 7.25 (IH, dd), 7.15 (IH, d), 7.10 (2H, s), 4.30 (2H, q), 1.35 (3H, t) | |
| 7.19 | A | Cl X | 7.30-7.25 (IH, m), 7.20 (IH, dd), 7.10-7.05 (IH, m), 7.05 (2H, s), 4.30 (2H, q), 1.35 (3H, t) |
| 7.20 | A | oc | 7.20-7.15 (IH, m), 7.05 (2H, s), 7.00-6.85 (2H, m), 4.30 (2H, q), 1.35 (3H, t) |
| 7.21 | V' | 7.40-7.35 (IH, m), 7.05 (2H, s), 7.00-6.90 (3H, m), 4.30 (2H, q), 1.35 (3H, t) | |
| 7.22 | X | 7.30 (IH, dd), 7.05 (2H, s), 6.80 (IH, d), 6.75 (IH, d), 6.80 (IH, s), 4.30 (2H,q), 3.80 (3H, s), 1.35 (3H, t) | |
| 7.23 | o; | 7.05 (2H, s), 7.00-6.90 (3H, m), 4.30 (2H, q), 2.35 {3H, s), 2.10 (3H, s), 1.35 (3H, t) | |
| 7.24 | î | X | 7.75-7.65 (2H, m), 7.40-7.35 (2H, m), 7.10 (2H, d), 4.30 (2H,q), 1.35 (3H, t) |
| 7.25 | X | 7.30 (IH, dd), 7.10 (IH, d), 7.05 (2H, s), 7.00 (IH, s), 6.95 (IH, d) |
| 7.26 | “X | 7.25-7.10 (3Η, m), 7.05 (2Η, s), 4.30 (2H, q), 1.35 (3H, t) |
| 7.27 | Γ | 7.95 (lH,d), 7.80 (IH, s), 7.50 (IH, dd), 7.35 (IH, d), 7.05 (2H, s), 4.40 (2H, q), 4.30 (2H, q), 1.40 (3H, t), 1.35 (3H, t) |
| 7.28 | 7.10 (IH, d), 7.05 (2H, s), 7.00 (IH, s), 6.85 (2H, d), 4.30 (2H, q), 3.80 (3H, s), 1.35 (3H, t) | |
| 7.29 | 7.25 (2H,d), 7.05 (2H, d), 7.00 (2H, s), 4.30 (2H, q), 3.60 (2H, t), 3.35 (3H, s), 2.90 (2H,t), 1.35 (3H,t) |
Claims (10)
- A formulation comprising a compound of formula (I)O (i) where R1 and R2 are each independently hydrogen, optionally substituted Cm g alkyl, optionally substituted Cm alkenyl, optionally substituted Ci.g cycloalkyl, optionally substituted C3_8 cycloalkenyl or optionally substituted aryl; provided that the total number of carbon atoms in R and R2 is an integer from 5 to 40 inclusive.
- 2. A formulation as claimed in claim 1 where the formulation is an emulsifiable concentrate or émulsion.
- 3. A formulation as claimed in claim 1 or 2 where the formulation is an agrochemical formulation.
- 4. A formulation as claimed in claim 1, 2 or 3 provided that the total number of carbon atoms in R1 and R2 is an integer from 5 to 20 inclusive.
- 5 hydrogen, methyl, ethyl, linear or branched propyl, or linear or branched butyl.17. A compound of formula (I) as claimed in claim 11 where R2 is propyl or butyl and R1 is butyl.5. A formulation as claimed in claim 1,2, 3 or 4 where optionally substituted aryl Ls substituted or unsubstituted phenyl or substituted or unsubstituted tolyl.
- 6. A formulation as claimed in claim 1, 2, 3, 4 or 5 where R1 is hydrogen or Ci-u alkyl optionally substituted by one, two or three hydroxyl groups.
- 7. A formulation as claimed in claim 1, 2, 3, 4, 5, or 6 where R2 is C3-is alkyl optionally substituted by one, two or three hydroxyl groups.
- 8. A formulation as claimed in claim 1,2,3, 4, 5, 6 or 7 where R1 is hydrogen, methyl, ethyl, linear or branched propyl, or linear or branched butyl.
- 9. A formulation as claimed in claim 1,2 or 3 where R2 is propyl or butyl and R1 is butyl.10. A formulation as claimed in claim 1,2 or 3 where R1 is hydrogen or Ci_2 alkyl and R2 is substituted or unsubstituted phenyl.11. A compound of formula (I)O where R’ and R2 are each independently hydrogen, optionally substituted Ci.;g alkyl, optionally substituted Cm® alkenyl, optionally substituted C3_g cycloalkyl or optionally substituted C3_8 cycloalkenyl; provided that the total number of carbon atoms in R1 and R2 is an integer from 5 to 40 inclusive; and provided that when R1 is CH3CH2CH2, (CH3)jC, (CH3)2CH, CH3CH2CH2CH2, (CH3)2CHCH2, CH3CH2CH2CH2CH2, CH3CH2CH2CH(OH)CH2, CH3CH(CH3)CH2CH2, ch3ch2ch2ch2ch2 ch2, CH3CH2CH2CH(CH3)C(OH), CH3CH2CH(CH3)CH2C(OH), CH3CH2CH2CH2CH2(CH2CH3)CH2, hexafluoroisopropyl, hydroxyisopropyl, cyclohexyl, cinacalcet, formoterol, HOCH2CH2CH2S03, CH3CHOHCH2SO3, CH3CH(C(CH3)3)CH2CH(CH3)CH2 or CH3CH(CH3)CH2CH2C(OH), then R2 is not the same as R1 ; when R1 is CH3CH(CH3) then R2 is not perfluorohexylethyl, perfluorooctylethyl, (CH3)3C, CH3CII(CH3)CH2 or cyclohexyl; when R3 is cyclohexyl then R2 is not CH3CH(CH3)CH2 or (CH3)3C; and when R1 is hydrogen then R2 is not stcaryl.12. A compound of formula (I) as claimed in claim 11 provided that the total number of carbon atoms in R1 and R2 is an integer from 5 to 20 inclusive.13. A compound of formula (I) as claimed in claim 11 or 12 where optionally substituted aryl is substituted or unsubstituted phenyl or substituted or unsubstituted tolyl,14. A compound of formula (I) as claimed in claim 11, 12 or 13 where R1 is hydrogen or Ci-is alkyl optionally substituted by one, two or three hydroxyl groups.15. A compound of formula (I) as claimcd in claim 11, 12, 13 or 14 where R2 is C3_j8 alkyl optionally substituted by one, two or three hydroxyl groups.16. A compound of formula (I) as claimed in claim 11, 12, 13, 14 or 15 where R1 îs
- 10 18. A compound of formula (I) as claimcd in claim 11, 12 or 13 where R1 is hydrogen orCi-2alkyl and R2 is substituted or unsubstituted phenyl.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1012587.0 | 2010-07-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| OA16303A true OA16303A (en) | 2015-04-24 |
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