WO1996022020A1 - Compositions pesticides - Google Patents
Compositions pesticides Download PDFInfo
- Publication number
- WO1996022020A1 WO1996022020A1 PCT/GB1996/000087 GB9600087W WO9622020A1 WO 1996022020 A1 WO1996022020 A1 WO 1996022020A1 GB 9600087 W GB9600087 W GB 9600087W WO 9622020 A1 WO9622020 A1 WO 9622020A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- ester
- composition
- pesticidal
- log
- value
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 30
- 230000000361 pesticidal effect Effects 0.000 title claims abstract description 26
- 150000002148 esters Chemical class 0.000 claims abstract description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 3
- 125000003158 alcohol group Chemical group 0.000 claims abstract description 3
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 3
- 150000005690 diesters Chemical class 0.000 claims abstract description 3
- 125000004185 ester group Chemical group 0.000 claims abstract description 3
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 3
- HGASFNYMVGEKTF-UHFFFAOYSA-N octan-1-ol;hydrate Chemical compound O.CCCCCCCCO HGASFNYMVGEKTF-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000005192 partition Methods 0.000 claims abstract description 3
- 150000005691 triesters Chemical class 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 23
- 230000000855 fungicidal effect Effects 0.000 claims description 14
- 239000005785 Fluquinconazole Substances 0.000 claims description 12
- IJJVMEJXYNJXOJ-UHFFFAOYSA-N fluquinconazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1N1C(=O)C2=CC(F)=CC=C2N=C1N1C=NC=N1 IJJVMEJXYNJXOJ-UHFFFAOYSA-N 0.000 claims description 12
- -1 succinate diester Chemical class 0.000 claims description 11
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 6
- QQQMUBLXDAFBRH-UHFFFAOYSA-N dodecyl 2-hydroxypropanoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)O QQQMUBLXDAFBRH-UHFFFAOYSA-N 0.000 claims description 6
- 229930195729 fatty acid Natural products 0.000 claims description 6
- 239000000194 fatty acid Substances 0.000 claims description 6
- 150000004665 fatty acids Chemical class 0.000 claims description 6
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- GLCFQKXOQDQJFZ-UHFFFAOYSA-N 2-ethylhexyl 12-hydroxyoctadecanoate Chemical compound CCCCCCC(O)CCCCCCCCCCC(=O)OCC(CC)CCCC GLCFQKXOQDQJFZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- SFAAOBGYWOUHLU-UHFFFAOYSA-N 2-ethylhexyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(CC)CCCC SFAAOBGYWOUHLU-UHFFFAOYSA-N 0.000 claims description 3
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 claims description 3
- 235000013162 Cocos nucifera Nutrition 0.000 claims description 3
- 244000060011 Cocos nucifera Species 0.000 claims description 3
- 241000607479 Yersinia pestis Species 0.000 claims description 3
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- KWABLUYIOFEZOY-UHFFFAOYSA-N dioctyl butanedioate Chemical compound CCCCCCCCOC(=O)CCC(=O)OCCCCCCCC KWABLUYIOFEZOY-UHFFFAOYSA-N 0.000 claims description 3
- BORJONZPSTVSFP-UHFFFAOYSA-N tetradecyl 2-hydroxypropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)C(C)O BORJONZPSTVSFP-UHFFFAOYSA-N 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
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- 230000003032 phytopathogenic effect Effects 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 150000003626 triacylglycerols Chemical class 0.000 claims description 2
- 239000000417 fungicide Substances 0.000 description 29
- 241000196324 Embryophyta Species 0.000 description 12
- 238000011282 treatment Methods 0.000 description 7
- 238000009472 formulation Methods 0.000 description 5
- 239000005654 Clofentezine Substances 0.000 description 4
- UXADOQPNKNTIHB-UHFFFAOYSA-N clofentezine Chemical compound ClC1=CC=CC=C1C1=NN=C(C=2C(=CC=CC=2)Cl)N=N1 UXADOQPNKNTIHB-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- AXISYYRBXTVTFY-UHFFFAOYSA-N Isopropyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OC(C)C AXISYYRBXTVTFY-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 230000035515 penetration Effects 0.000 description 3
- 239000000575 pesticide Substances 0.000 description 3
- 230000028070 sporulation Effects 0.000 description 3
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- ZMYFCFLJBGAQRS-IRXDYDNUSA-N (2R,3S)-epoxiconazole Chemical compound C1=CC(F)=CC=C1[C@@]1(CN2N=CN=C2)[C@H](C=2C(=CC=CC=2)Cl)O1 ZMYFCFLJBGAQRS-IRXDYDNUSA-N 0.000 description 2
- RYAUSSKQMZRMAI-ALOPSCKCSA-N (2S,6R)-4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1C[C@H](C)O[C@H](C)C1 RYAUSSKQMZRMAI-ALOPSCKCSA-N 0.000 description 2
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000005828 Pyrimethanil Substances 0.000 description 2
- 239000005839 Tebuconazole Substances 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 230000000895 acaricidal effect Effects 0.000 description 2
- 239000000642 acaricide Substances 0.000 description 2
- 229960002587 amitraz Drugs 0.000 description 2
- QXAITBQSYVNQDR-ZIOPAAQOSA-N amitraz Chemical compound C=1C=C(C)C=C(C)C=1/N=C/N(C)\C=N\C1=CC=C(C)C=C1C QXAITBQSYVNQDR-ZIOPAAQOSA-N 0.000 description 2
- HJJVPARKXDDIQD-UHFFFAOYSA-N bromuconazole Chemical compound ClC1=CC(Cl)=CC=C1C1(CN2N=CN=C2)OCC(Br)C1 HJJVPARKXDDIQD-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- HAORKNGNJCEJBX-UHFFFAOYSA-N cyprodinil Chemical compound N=1C(C)=CC(C2CC2)=NC=1NC1=CC=CC=C1 HAORKNGNJCEJBX-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- RMFNNCGOSPBBAD-MDWZMJQESA-N formetanate Chemical compound CNC(=O)OC1=CC=CC(\N=C\N(C)C)=C1 RMFNNCGOSPBBAD-MDWZMJQESA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 238000003359 percent control normalization Methods 0.000 description 2
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 2
- 150000003431 steroids Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 2
- WRGKWWRFSUGDPX-HUUCEWRRSA-N (1R,2R)-1-(4-chlorophenyl)-2-(1,2,4-triazol-1-yl)cycloheptan-1-ol Chemical compound N1([C@@H]2CCCCC[C@@]2(O)C=2C=CC(Cl)=CC=2)C=NC=N1 WRGKWWRFSUGDPX-HUUCEWRRSA-N 0.000 description 1
- SAPGTCDSBGMXCD-UHFFFAOYSA-N (2-chlorophenyl)-(4-fluorophenyl)-pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(F)C=C1 SAPGTCDSBGMXCD-UHFFFAOYSA-N 0.000 description 1
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- PZBPKYOVPCNPJY-UHFFFAOYSA-N 1-[2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=C)CN1C=NC=C1 PZBPKYOVPCNPJY-UHFFFAOYSA-N 0.000 description 1
- MGNFYQILYYYUBS-UHFFFAOYSA-N 1-[3-(4-tert-butylphenyl)-2-methylpropyl]piperidine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1CCCCC1 MGNFYQILYYYUBS-UHFFFAOYSA-N 0.000 description 1
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- HZJKXKUJVSEEFU-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)hexanenitrile Chemical compound C=1C=C(Cl)C=CC=1C(CCCC)(C#N)CN1C=NC=N1 HZJKXKUJVSEEFU-UHFFFAOYSA-N 0.000 description 1
- 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 1
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- WURGXGVFSMYFCG-UHFFFAOYSA-N dichlofluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=CC=C1 WURGXGVFSMYFCG-UHFFFAOYSA-N 0.000 description 1
- LNJNFVJKDJYTEU-UHFFFAOYSA-N diethofencarb Chemical compound CCOC1=CC=C(NC(=O)OC(C)C)C=C1OCC LNJNFVJKDJYTEU-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000007865 diluting Methods 0.000 description 1
- FBOUIAKEJMZPQG-BLXFFLACSA-N diniconazole-M Chemical compound C1=NC=NN1/C([C@H](O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1Cl FBOUIAKEJMZPQG-BLXFFLACSA-N 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 229960002125 enilconazole Drugs 0.000 description 1
- FKLFBQCQQYDUAM-UHFFFAOYSA-N fenpiclonil Chemical compound ClC1=CC=CC(C=2C(=CNC=2)C#N)=C1Cl FKLFBQCQQYDUAM-UHFFFAOYSA-N 0.000 description 1
- UZCGKGPEKUCDTF-UHFFFAOYSA-N fluazinam Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=NC=C(C(F)(F)F)C=C1Cl UZCGKGPEKUCDTF-UHFFFAOYSA-N 0.000 description 1
- MUJOIMFVNIBMKC-UHFFFAOYSA-N fludioxonil Chemical compound C=12OC(F)(F)OC2=CC=CC=1C1=CNC=C1C#N MUJOIMFVNIBMKC-UHFFFAOYSA-N 0.000 description 1
- FQKUGOMFVDPBIZ-UHFFFAOYSA-N flusilazole Chemical compound C=1C=C(F)C=CC=1[Si](C=1C=CC(F)=CC=1)(C)CN1C=NC=N1 FQKUGOMFVDPBIZ-UHFFFAOYSA-N 0.000 description 1
- PTCGDEVVHUXTMP-UHFFFAOYSA-N flutolanil Chemical compound CC(C)OC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1 PTCGDEVVHUXTMP-UHFFFAOYSA-N 0.000 description 1
- HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- KGVPNLBXJKTABS-UHFFFAOYSA-N hymexazol Chemical compound CC1=CC(O)=NO1 KGVPNLBXJKTABS-UHFFFAOYSA-N 0.000 description 1
- AGKSTYPVMZODRV-UHFFFAOYSA-N imibenconazole Chemical compound C1=CC(Cl)=CC=C1CSC(CN1N=CN=C1)=NC1=CC=C(Cl)C=C1Cl AGKSTYPVMZODRV-UHFFFAOYSA-N 0.000 description 1
- ONUFESLQCSAYKA-UHFFFAOYSA-N iprodione Chemical compound O=C1N(C(=O)NC(C)C)CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 ONUFESLQCSAYKA-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- CIFWZNRJIBNXRE-UHFFFAOYSA-N mepanipyrim Chemical compound CC#CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 CIFWZNRJIBNXRE-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- XWPZUHJBOLQNMN-UHFFFAOYSA-N metconazole Chemical compound C1=NC=NN1CC1(O)C(C)(C)CCC1CC1=CC=C(Cl)C=C1 XWPZUHJBOLQNMN-UHFFFAOYSA-N 0.000 description 1
- ZQEIXNIJLIKNTD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- BEGLCMHJXHIJLR-UHFFFAOYSA-N methylisothiazolinone Chemical compound CN1SC=CC1=O BEGLCMHJXHIJLR-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- XGXNTJHZPBRBHJ-UHFFFAOYSA-N n-phenylpyrimidin-2-amine Chemical compound N=1C=CC=NC=1NC1=CC=CC=C1 XGXNTJHZPBRBHJ-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003151 ovacidal effect Effects 0.000 description 1
- OGYFATSSENRIKG-UHFFFAOYSA-N pencycuron Chemical compound C1=CC(Cl)=CC=C1CN(C(=O)NC=1C=CC=CC=1)C1CCCC1 OGYFATSSENRIKG-UHFFFAOYSA-N 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 125000005543 phthalimide group Chemical group 0.000 description 1
- WHHIPMZEDGBUCC-UHFFFAOYSA-N probenazole Chemical compound C1=CC=C2C(OCC=C)=NS(=O)(=O)C2=C1 WHHIPMZEDGBUCC-UHFFFAOYSA-N 0.000 description 1
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 1
- QXJKBPAVAHBARF-BETUJISGSA-N procymidone Chemical compound O=C([C@]1(C)C[C@@]1(C1=O)C)N1C1=CC(Cl)=CC(Cl)=C1 QXJKBPAVAHBARF-BETUJISGSA-N 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- WZZLDXDUQPOXNW-UHFFFAOYSA-N propamocarb Chemical compound CCCOC(=O)NCCCN(C)C WZZLDXDUQPOXNW-UHFFFAOYSA-N 0.000 description 1
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
- XRJLAOUDSILTFT-UHFFFAOYSA-N pyroquilon Chemical compound O=C1CCC2=CC=CC3=C2N1CC3 XRJLAOUDSILTFT-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- WOSNCVAPUOFXEH-UHFFFAOYSA-N thifluzamide Chemical compound S1C(C)=NC(C(F)(F)F)=C1C(=O)NC1=C(Br)C=C(OC(F)(F)F)C=C1Br WOSNCVAPUOFXEH-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- 239000004562 water dispersible granule Substances 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
- A01N37/04—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof polybasic
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group, wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
Definitions
- This invention concerns pesticidal compositions. Background to the invention
- Pesticidal compounds particularly those used for crop protection, are commonly used in the form of compositions containing one or more co-formulants, for example surfactants. We have found that a new group of compounds, not previously used in association with pesticidal compounds, can also be used with advantage in association with pesticidal compounds.
- the invention provides the use in a pesticidal composition of at least one aliphatic mono-, di- or triester, optionally substituted by one or more hydroxy groups, said ester(s) having: i) a log octanol-water partition coefficient (log P) of from 5 to 13.1, ii) an equivalent hydrocarbon (EH) value of from 20 to 42; the EH value being calculated as the number of carbon atoms plus five for any hydroxy group present plus 3 for each ester group, and iii) an alcohol moiety comprising at least 2 carbon atoms.
- log P log octanol-water partition coefficient
- EH equivalent hydrocarbon
- ester of the invention' is used herein to indicate an ester having the above properties.
- the invention provides a pesticidal composition which comprises a pesticidal compound and at least one ester of the invention.
- the invention provides a method of combating pests at a locus infested or liable to be infested therewith which comprises applying to said locus an effective amount of a pesticidal composition which comprises a pesticidal compound and at least one ester of the invention.
- the log P value of an ester as that term is used herein is that calculated from the structure of the compound using the clog P Program, Pomona College Med Chem release 3.54, January 1988, provided by Daylight Chemical Information Systems Inc, Claremont, California.
- the values generated by this program correlate well in general with those determined experimentally by methods well known to those skilled in the art, but such methods are difficult to apply accurately to compounds having log P values within the scope of this invention, and we therefore use the calculated values.
- the EH value can be simply calculated from the structure of each compound. Sometimes, however, the esters of the invention occur or are presented as mixtures of individual compounds, and the mixture will therefore include compounds of different EH values.
- the ratio of EH value to log P value is preferably in the range 2.4:1 to 4.15:1.
- esters of the invention are succinate diesters, lactic acid carboxylic esters, and esters resulting from esterification of a saturated acid of at least 12 carbon atoms with a branched chain alcohol.
- esters of the invention which have little or no pesticidal activity in their own right, surprisingly aid the penetration of the pesticidal compound into plant or pest tissue, thereby promoting enhanced activity, particularly of pesticidal compounds whose activity depends on such penetration.
- the pesticidal compound is especially one disclosed in The Pesticide Manual, 10th edition, published by Crop Protection Publications, and may for example be a herbicide, fungicide, insecticide or acaricide.
- phytopathogenic fungicide selected from:
- a conazole steroid demethylation inhibitor (i) a conazole steroid demethylation inhibitor; (ii) a steroid reduction inhibitor based on a l-[3-(4- tert-butylphenyl)-2-methylpropyl] group which is attached via the N-atom to piperidine or 2,6- dimethylmorpholine (iii) a dithiocarbamate fungicide (iv) a phthali ide fungicide in which a chloroalkylthio group is attached via the N-atom to the optionally hydrogenated phthalimide group, (v) an anilide fungicide (vi) an mbc fungicide. (vii) a carbamate fungicide
- a copper compound fungicide (ix) a tin compound fungicide (x) a strobilurin type fungicide, (xi) a 2-anilinopyrimidine fungicide or (x ⁇ ) a fungicide selected from the group consisting of chlorothalonil, dimethomorph, fenpiclonil, fluazinam, hymexazol, nuarimol, pencycuron, pyrifenox, thicyofen, probenazole, pyroquilon, tricyclazole, quaternary ammonium compounds.
- Conazoles are as defined in ISO standard 257, ie compounds based on imidazole or 1,2,4-triazole and containing a halogenated phenyl group.
- Examples include prochloraz (and its metal complexes, especially the manganese or copper complex) , propiconazole, flusilazole, hexaconazole, tebuconazole, difenoconazole, bromuconazole, cyproconazole, diniconazole, fenbuconazole, imibenconazole, furconazole, tetraconazole, myclobutanil, penconazole, fluquinconazole, azaconazole, imazalil, triflumizole, epoxiconazole, triticonazole, metconazole and the fungicide having the code No SSF 109.
- type (ii) fungicides include fenpropimorph and fenpropidin.
- type (iii) fungicides include mancozeb and thiram.
- type (iv) fungicides include folpet, captafol and captan.
- type (v) fungicides include a) 3' ,5'-dichloroanilide fungicides in which the anilino nitrogen comprises a ring carrying two oxo substituents, in positions adjacent the nitrogen, eg iprodione, vinclozolin or procymidone, or b) acetanilide fungicides, eg metalaxyl or ofurace, c) sulfanilide fungicides, eg dichlofluanid, d) benzanilide fungicides, eg flutolanil, and e) heteroarylanilide fungicides, eg thifluzamide.
- type (vi) fungicides include carbendazim, benomyl and thiophanate-methyl.
- type (vii) fungicides include diethofencarb and propamocarb.
- type (viii) fungicides include Bordeaux mixture, oxine-copper, copper oxychloride and copper naphthenate.
- type (ix) fungicides include tributyltin oxide and tributyltin naphthenate.
- Strobilurine type fungicides are methyl esters of arylacetic acid in which the acetic acid also carries a methoxymethylene or methoxyi ino substituent.
- the aryl group is usually a 2-substituted phenyl group.
- Examples of such compounds are those disclosed in a wide number of patent applications, including EPS 178826, 203606, 203608, 206523, 229974, 226917, 242070, 242081, 243012, 243014, 251082, 256667, 260794, 260832, 267734, 270252, 273572, 274825, 278595, 291196, 299694, 307101, 307103, 310954, 312221, 312243, 329011 and 336211.
- Specific compounds are those having the code Nos BAS 490F and ICIA 5504.
- type (xi) fungicides include pyrimethanil, mepanipyrim and cyprodinil.
- insecticides examples include amitraz, triazophos and formetanate.
- acaricides which may be used include clofentezine.
- the names quoted for these compounds are the non- proprietary common names and the chemical structures can be found for example by reference to The Pesticide Manual.
- the invention is particularly useful for pesticidal compounds of high melting point and/or low solubility in organic solvents. It is particularly applicable to fluquinconazole.
- esters of the invention may be incorporated in conventional concentrate formulations of the pesticidal compound (eg suspension concentrates, suspoemulsions or solid formulation types such as water dispersible granules) , which are diluted with water prior to application, or they may be added to the pesticidal composition just prior to use.
- conventional concentrate formulations of the pesticidal compound eg suspension concentrates, suspoemulsions or solid formulation types such as water dispersible granules
- the pesticidal composition may include small quantities of solvent and/or surfactant, especially a non-ionic surfactant, and other additives such as fatty acids, to improve the emulsifiability of the esters of the invention.
- solvent and/or surfactant especially a non-ionic surfactant, and other additives such as fatty acids
- the esters of the invention preferably comprise from 2 to 90% by weight of a concentrate formulation.
- the esters of the invention are preferably applied in a diluted formulation at a concentration of 20g to 2000g, preferably 50g to 500g, per 100 litres.
- the mixtures can be used for those applications where the pesticide would normally be used.
- fluquinconazole for example, it is preferably used in the direct treatment of growing crops, such as cereals and fruit, or in seed treatments.
- Clarkamol OHS is a trade name for 2-ethylhexyl 12- hydroxystearate
- Rodamol PC M is a trade name for propylene glycol diester of coconut fatty acids
- Crodamol IPP is a trade name for isopropyl palmitate
- Clarkamol IPM is a trade name for isopropyl myristate
- Crodamol OHS is a trade name for 2-ethylhexyl 12- hydroxystearate
- Electrodeamol OSU is a trade name for dioctyl succinate
- Rodamol OP is a trade name for 2-ethylhexyl palmitate
- Electromol ML is a trade name for myristyl lactate
- Clarkamol LL is a trade name for lauryl lactate.
- EC is epoxiconazole
- BC is bromuconazole
- TC is tebuconazole
- CP is cyprodinil
- TP is triazophos
- FM is formetanate.
- Results are given in the following table: gster ⁇ Mortality % Mort ity with CZ without cz Crodamol IPP 99 0
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Utilisation, dans une composition pesticide, d'au moins un mono-, di- ou triester aliphatique, éventuellement substitué par un ou plusieurs groupes hydroxy, ledit ou lesdits esters ayant: i) un log de coefficient de partage octanol-eau (log P) compris entre 5 et 13,1, ii) une valeur d'équivalent hydrocarbure (EH)comprise entre 20 et 42; la valeur EH étant calculée comme étant le nombre d'atomes de carbone plus cinq pour chaque groupe hydroxy présent, plus 3 pour chaque groupe ester, et iii) une fraction alcool comprenant au moins 2 atomes de carbone.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU43965/96A AU4396596A (en) | 1995-01-19 | 1996-01-17 | Pesticidal compositions |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9500983.3 | 1995-01-19 | ||
GBGB9500983.3A GB9500983D0 (en) | 1995-01-19 | 1995-01-19 | Pesticidal compositions |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1996022020A1 true WO1996022020A1 (fr) | 1996-07-25 |
Family
ID=10768208
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/GB1996/000087 WO1996022020A1 (fr) | 1995-01-19 | 1996-01-17 | Compositions pesticides |
Country Status (3)
Country | Link |
---|---|
AU (1) | AU4396596A (fr) |
GB (1) | GB9500983D0 (fr) |
WO (1) | WO1996022020A1 (fr) |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2744332A1 (fr) * | 1996-02-06 | 1997-08-08 | Basf Ag | Melange, produits phytosanitaires contenant ce melange et leur utilisation |
FR2756464A1 (fr) * | 1996-12-02 | 1998-06-05 | Rhone Poulenc Agrochimie | Association fongicide a effet synergique a base d'huile d'origine vegetale transformee |
WO2000024253A1 (fr) * | 1998-10-22 | 2000-05-04 | Aventis Cropscience S.A. | Utilisation de derives d'acide citrique comme adjuvants pesticides |
US6184182B1 (en) | 1996-10-25 | 2001-02-06 | Monsanto Company | Composition and method for treating plants with exogenous chemicals |
EP1604570A3 (fr) * | 2004-06-11 | 2006-01-18 | Luxan B.V. | Inhibiteur de germination pour pommes de terre |
WO2007028538A2 (fr) | 2005-09-09 | 2007-03-15 | Bayer Cropscience Aktiengesellschaft | Utilisation d'esters de lactate pour ameliorer l'action de produits phytosanitaires |
US7407979B2 (en) | 2001-04-12 | 2008-08-05 | Basf Aktiengesellschaft | Bioregulatory active ingredient combination |
WO2008128666A3 (fr) * | 2007-04-21 | 2009-09-24 | Cognis Ip Management Gmbh | Compositions agrochimiques |
US8349769B2 (en) | 2004-07-09 | 2013-01-08 | The New Zealand Institute For Plant And Food Research Limited | Fungicidal compositions |
WO2013014126A1 (fr) | 2011-07-26 | 2013-01-31 | Bayer Intellectual Property Gmbh | Esters de lactate ethérés, procédé de préparation et leur utilisation pour améliorer l'effet d'agents phytoprotecteurs |
WO2015145057A1 (fr) * | 2014-03-26 | 2015-10-01 | Oleon | Utilisation d'ester(s) d'acide(s) gras comme insecticide et /ou arachnicide |
US9414593B2 (en) | 2006-10-27 | 2016-08-16 | Syngenta Crop Protection, Llc | Herbicidal compositions |
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DE4239181A1 (de) * | 1992-11-03 | 1994-05-05 | Hoechst Ag | Wirkungsverstärkung von Neophanen, Azaneophanen und anderen Wirkstoffen durch Penetrationsmittel |
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1995
- 1995-01-19 GB GBGB9500983.3A patent/GB9500983D0/en active Pending
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1996
- 1996-01-17 WO PCT/GB1996/000087 patent/WO1996022020A1/fr active Application Filing
- 1996-01-17 AU AU43965/96A patent/AU4396596A/en not_active Abandoned
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FR2744332A1 (fr) * | 1996-02-06 | 1997-08-08 | Basf Ag | Melange, produits phytosanitaires contenant ce melange et leur utilisation |
US6479434B1 (en) | 1996-10-25 | 2002-11-12 | Monsanto Technology Llc | Composition and method for treating plants with exogenous chemicals |
US6184182B1 (en) | 1996-10-25 | 2001-02-06 | Monsanto Company | Composition and method for treating plants with exogenous chemicals |
FR2756464A1 (fr) * | 1996-12-02 | 1998-06-05 | Rhone Poulenc Agrochimie | Association fongicide a effet synergique a base d'huile d'origine vegetale transformee |
US6551964B1 (en) | 1998-10-22 | 2003-04-22 | Bayer Cropscience S.A. | Use of citric acid derivatives as pesticidal adjuvants |
JP2002528395A (ja) * | 1998-10-22 | 2002-09-03 | アベンティス・クロップサイエンス・エス・アー | 農薬補助剤としてのクエン酸誘導体の使用 |
EP1586238A3 (fr) * | 1998-10-22 | 2010-03-03 | Bayer CropScience S.A. | Utilisation de derivés d'acide citrique comme adjuvants pour des herbicides |
EP1586238A2 (fr) | 1998-10-22 | 2005-10-19 | Bayer CropScience S.A. | Utilisation de derivés d'acide citrique comme adjuvants pour des herbicides |
WO2000024253A1 (fr) * | 1998-10-22 | 2000-05-04 | Aventis Cropscience S.A. | Utilisation de derives d'acide citrique comme adjuvants pesticides |
US7407979B2 (en) | 2001-04-12 | 2008-08-05 | Basf Aktiengesellschaft | Bioregulatory active ingredient combination |
EP1604570A3 (fr) * | 2004-06-11 | 2006-01-18 | Luxan B.V. | Inhibiteur de germination pour pommes de terre |
US9510600B2 (en) | 2004-07-09 | 2016-12-06 | The New Zealand Institute For Plant And Food Research Limited | Fungicidal compositions |
US8349769B2 (en) | 2004-07-09 | 2013-01-08 | The New Zealand Institute For Plant And Food Research Limited | Fungicidal compositions |
EP1926369B1 (fr) | 2005-09-09 | 2015-06-17 | Bayer Intellectual Property GmbH | Utilisation d'esters de lactate pour ameliorer l'action de produits phytosanitaires |
EA014782B1 (ru) * | 2005-09-09 | 2011-02-28 | Байер Кропсайенс Аг | Сложные эфиры молочной кислоты в качестве агента для улучшения воздействия пестицидов на растения, способ улучшения воздействия пестицидов |
AU2006289348B2 (en) * | 2005-09-09 | 2011-04-21 | Bayer Intellectual Property Gmbh | Use of lactate esters for improving the action of agricultural pesticides |
WO2007028538A3 (fr) * | 2005-09-09 | 2007-05-31 | Bayer Cropscience Ag | Utilisation d'esters de lactate pour ameliorer l'action de produits phytosanitaires |
WO2007028538A2 (fr) | 2005-09-09 | 2007-03-15 | Bayer Cropscience Aktiengesellschaft | Utilisation d'esters de lactate pour ameliorer l'action de produits phytosanitaires |
US9414593B2 (en) | 2006-10-27 | 2016-08-16 | Syngenta Crop Protection, Llc | Herbicidal compositions |
WO2008128666A3 (fr) * | 2007-04-21 | 2009-09-24 | Cognis Ip Management Gmbh | Compositions agrochimiques |
WO2013014126A1 (fr) | 2011-07-26 | 2013-01-31 | Bayer Intellectual Property Gmbh | Esters de lactate ethérés, procédé de préparation et leur utilisation pour améliorer l'effet d'agents phytoprotecteurs |
US9826734B2 (en) | 2011-07-26 | 2017-11-28 | Clariant International Ltd. | Etherified lactate esters, method for the production thereof and use thereof for enhancing the effect of plant protecting agents |
WO2015145057A1 (fr) * | 2014-03-26 | 2015-10-01 | Oleon | Utilisation d'ester(s) d'acide(s) gras comme insecticide et /ou arachnicide |
FR3019002A1 (fr) * | 2014-03-26 | 2015-10-02 | Novance | Utilisation d'ester(s) d'acide(s) gras comme insecticide. |
US10045531B2 (en) | 2014-03-26 | 2018-08-14 | Oleon Nv | Use of one or more fatty acid esters as insecticide and/or arachnicide |
Also Published As
Publication number | Publication date |
---|---|
AU4396596A (en) | 1996-08-07 |
GB9500983D0 (en) | 1995-03-08 |
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