EP1962595A1 - Insecticidal compositions having improved effect - Google Patents
Insecticidal compositions having improved effectInfo
- Publication number
- EP1962595A1 EP1962595A1 EP06829188A EP06829188A EP1962595A1 EP 1962595 A1 EP1962595 A1 EP 1962595A1 EP 06829188 A EP06829188 A EP 06829188A EP 06829188 A EP06829188 A EP 06829188A EP 1962595 A1 EP1962595 A1 EP 1962595A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- optionally substituted
- formula
- hydrogen
- phenyl
- 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.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims description 36
- 230000000749 insecticidal effect Effects 0.000 title claims description 5
- 230000001976 improved effect Effects 0.000 title description 2
- 230000035515 penetration Effects 0.000 claims abstract description 29
- 230000000694 effects Effects 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 11
- NAYYNDKKHOIIOD-UHFFFAOYSA-N phthalamide Chemical class NC(=O)C1=CC=CC=C1C(N)=O NAYYNDKKHOIIOD-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000011814 protection agent Substances 0.000 claims abstract description 10
- 239000013543 active substance Substances 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 34
- -1 pentaborate Chemical compound 0.000 claims description 33
- 150000002431 hydrogen Chemical class 0.000 claims description 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 25
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical group 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 239000004480 active ingredient Substances 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000007921 spray Substances 0.000 claims description 8
- 241000238631 Hexapoda Species 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 6
- 239000008158 vegetable oil Substances 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 241000196324 Embryophyta Species 0.000 claims description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000002480 mineral oil Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 239000004476 plant protection product Substances 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 3
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 3
- 229910002651 NO3 Inorganic materials 0.000 claims description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 claims description 3
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 3
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 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 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 claims description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-L 2-(carboxymethyl)-2-hydroxysuccinate Chemical compound [O-]C(=O)CC(O)(C(=O)O)CC([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-L 0.000 claims description 2
- GDTSJMKGXGJFGQ-UHFFFAOYSA-N 3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound O1B([O-])OB2OB([O-])OB1O2 GDTSJMKGXGJFGQ-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 2
- 241000607479 Yersinia pestis Species 0.000 claims description 2
- 150000001449 anionic compounds Chemical class 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 2
- 150000002891 organic anions Chemical class 0.000 claims description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 229940095064 tartrate Drugs 0.000 claims description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 2
- 235000010446 mineral oil Nutrition 0.000 claims 2
- 125000000373 fatty alcohol group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- 150000004714 phosphonium salts Chemical class 0.000 abstract description 14
- 239000003623 enhancer Substances 0.000 abstract description 2
- 150000003863 ammonium salts Chemical class 0.000 abstract 2
- 229910052731 fluorine Inorganic materials 0.000 description 25
- 239000011737 fluorine Substances 0.000 description 25
- 239000000460 chlorine Chemical group 0.000 description 23
- 229910052801 chlorine Inorganic materials 0.000 description 23
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 22
- 125000001153 fluoro group Chemical group F* 0.000 description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 14
- 229910052794 bromium Inorganic materials 0.000 description 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 238000009472 formulation Methods 0.000 description 8
- 125000005913 (C3-C6) cycloalkyl group Chemical class 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 125000004076 pyridyl group Chemical group 0.000 description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
- 239000003905 agrochemical Substances 0.000 description 4
- 239000000575 pesticide Substances 0.000 description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 3
- 230000001276 controlling effect Effects 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 125000000335 thiazolyl group Chemical group 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 235000019486 Sunflower oil Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 230000000875 corresponding effect Effects 0.000 description 2
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 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 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- 125000006413 ring segment Chemical group 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 239000002600 sunflower oil Substances 0.000 description 2
- 125000001425 triazolyl group Chemical group 0.000 description 2
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 description 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 1
- FOGYNLXERPKEGN-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfopropyl)phenoxy]propane-1-sulfonic acid Chemical class COC1=CC=CC(CC(CS(O)(=O)=O)OC=2C(=CC(CCCS(O)(=O)=O)=CC=2)OC)=C1O FOGYNLXERPKEGN-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 239000005562 Glyphosate Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- IAJOBQBIJHVGMQ-UHFFFAOYSA-N Phosphinothricin Natural products CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000001204 arachidyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl group Chemical group [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])* 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical class O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
- IAJOBQBIJHVGMQ-BYPYZUCNSA-N glufosinate-P Chemical compound CP(O)(=O)CC[C@H](N)C(O)=O IAJOBQBIJHVGMQ-BYPYZUCNSA-N 0.000 description 1
- 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 description 1
- 229940097068 glyphosate Drugs 0.000 description 1
- XDDAORKBJWWYJS-UHFFFAOYSA-M glyphosate(1-) Chemical compound OP(O)(=O)CNCC([O-])=O XDDAORKBJWWYJS-UHFFFAOYSA-M 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001421 myristyl 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])[H] 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000000913 palmityl 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])[H] 0.000 description 1
- 239000003961 penetration enhancing agent Substances 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000010499 rapseed oil Substances 0.000 description 1
- 102000042094 ryanodine receptor (TC 1.A.3.1) family Human genes 0.000 description 1
- 108091052345 ryanodine receptor (TC 1.A.3.1) family Proteins 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 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
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000004094 surface-active agent 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
- A01N37/36—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
- A01N37/38—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 having at least one oxygen or sulfur atom attached to an aromatic ring system
- A01N37/40—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 having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/12—Quaternary ammonium compounds
-
- 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
- A01N37/18—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 —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/22—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 —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
-
- 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
- A01N37/18—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 —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/30—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 —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the groups —CO—N< and, both being directly attached by their carbon atoms to the same carbon skeleton, e.g. H2N—NH—CO—C6H4—COOCH3; 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/10—Sulfones; Sulfoxides
-
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom not containing sulfur-to-oxygen bonds, e.g. polysulfides
Definitions
- the present invention relates to the enhancement of the action of crop protection agents containing certain phthalic diamides by the addition of ammonium or phosphonium salts and optionally penetration promoters, the corresponding agents, processes for their preparation and their use in crop protection.
- Phthalic diamides are known as compounds having insecticidal properties (cf., EP-A-0 919 542, EP-A-006 107, WO 01/00575, WO 01/00599, WO 01/46 124, JP-A 2001-33 555 9 , WO 01/02354, WO 01/21 576, WO 02/08 8074, WO 02/08 8075, WO 02/09 4765, WO 02/09 4766, WO 02/06 2807).
- Such phthalic diamides are described by the formula (I):
- X B is halogen, cyano, Ci-C 8 alkyl, C, -C r haloalkyl, C, -C 8 alkoxy or C 1 -C 8 - haloalkoxy,
- R IB , R 2B and R 3B are independently hydrogen, cyano, optionally substituted by
- M 1B is optionally substituted achiral C r Ci 2 alkylene, achiral C 3 -C 2 alkenylene or achiral C 3 -C
- Q B is hydrogen, halogen, cyano, nitro, Ci-C8 haloalkyl, each optionally substituted C 3 -C 8 -Cy loalky I, Cj-Cs-alkyl-carbonyl or Ci-C 8 -alkoxy-carbonyl, JE T? _R 4B because optionally substituted phenyl, hetaryl or represents the group,
- T B is oxygen, -S (O) n , - or -N (R 5B ) -, R 4B R is hydrogen, optionally substituted Ci C 2 alkyl, C 3 -C 2 -AIkenyl, C 3 - C, 2 alkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 -CycloalkyI-C, -C 6 alkyl, C, -C 6 alkoxy-C
- R 5B is hydrogen, in each case optionally substituted C 1 -C 8 -alkyl-carbonyl, C r C 8 -
- k 1, 2, 3, or 4
- n 0, 1 or 2
- R IB and R 2B together form an optionally substituted 4- to 7-membered ring which may optionally be interrupted by heteroatoms,
- L 1B and L 3B are each independently hydrogen, halogen, cyano or optionally substituted C, -C 8 alkyl, C r C 8 alkoxy, Ci-C 6 alkyl-S (O) m -, phenyl, phenoxy or Hetaryloxy stand,
- L 2B represents hydrogen, halogen, cyano, respectively optionally substituted Ci-C) 2 alkyl, C 2 - C, 2 alkenyl, C2-Ci2 alkynyl, C r C 2 haloalkyl, C 3 -C 8 - Cycloalkyl, phenyl, hetaryl M 2B R 6B or represents the group,
- M 2B is oxygen or -S (O) m -
- R 6B is in each case optionally substituted C 1 -C 8 -alkyl, C 2 -C 8 -alkenyl, C 3 -C 6 -alkynyl C 3 -C 8 -cycloalkyl, phenyl or hetaryl,
- L 1B and L 3B or L 1B and L 2B each together form an optionally substituted 5- to 6-membered ring which may optionally be interrupted by heteroatoms,
- the insecticidal phthalic diamides are generally defined by the formula (I). Preferred substituents or ranges of the radicals listed in the formulas mentioned above and below are explained below:
- X B is preferably fluorine, chlorine, bromine, iodine, cyano, C r C 6 alkyl, C r C 6 haloalkyl, C 1 - C ⁇ -alkoxy or Ci-C -haloalkoxy ö.
- R IB , R 2B and R 3B independently of one another preferably represent hydrogen, cyano, for
- M 1B preferably represents achiral C r C 8 -alkylene, achiral C 3 -C 6 -alkenylene or achiral C 3 - C ⁇ -alkynylene.
- Q B preferably represents hydrogen, halogen, cyano, nitro, C
- Haloalkoxy, cyano or nitro substituted phenyl or hetaryl having 5 to 6 ring atoms for example, furanyl, pyridyl, imidazolyl, triazolyl, pyrazolyl, pyrimidyl, thiazole or thienyl
- group for example, furanyl, pyridyl, imidazolyl, triazolyl, pyrazolyl, pyrimidyl, thiazole or thienyl
- T B is preferably oxygen, -S (O) n , - or -N (R 58 ) -.
- R 4B preferably represents hydrogen, in each case optionally fluorine- and / or chlorine-substituted C 1 -C 6 -alkyl, C 3 -C 8 -alkenyl, C 3 -C 8 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 - C 8 - cycloalkyl-C 1 -C 2 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, in each case optionally monosubstituted to tetravalent by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy , Ci-C 4 - haloalkyl, Ci-C4 haloalkoxy, nitro or cyano-substituted phenyl, phenyl-Cr Q-alkyl, phenyl-C, -C 4 alkoxy,
- Ring atoms has (for example, furanyl, pyridyl, imidazolyl, triazolyl, pyrazolyl, pyrimidyl, thiazolyl or thienyl).
- R 5B preferably represents hydrogen, in each case optionally substituted by fluorine and / or chlorine, C 1 -C 6 -alkyl-carbonyl, C 1 -C 6 -alkoxycarbonyl, in each case optionally monosubstituted to trisubstituted by halogen, C 1 -C 6 -alkyl, C r C 6 alkoxy, C 1 -C 4 haloalkyl, C r
- k is preferably 1, 2 or 3.
- n is preferably 0, 1 or 2.
- R 1B and R 2B together preferably form a 5- to 6-membered ring which may optionally be interrupted by an oxygen or sulfur atom.
- L 1B and L 3B are each independently preferably represents hydrogen, cyano, fluorine, chlorine, bromine, iodine, C, -C 6 alkyl, C r C 4 haloalkyl, C, -C6 alkoxy, C, -C 4 -haloalkoxy, C 1 -C 4 - alkyl-S (O) m -, C 4 haloalkyl-S (O) m -, in each case optionally mono- to trisubstituted by fluorine, chlorine, bromine, C r C 6 - Alkyl, C, -C 6 alkoxy, C, -C 4 -haloalkyl, C 1 -C 4 - haloalkoxy, cyano or nitro-substituted phenyl, phenoxy, pyrdinyloxy, thiazoloxoxy or pyrimidinyloxy.
- L 2B is preferably hydrogen, fluorine, chlorine, bromine, iodine, cyano, represents in each case, where appropriate, by fluorine and / or chlorine-substituted C r C 10 alkyl, C 2 -C 0 alkenyl, C 2 -C 6 -
- Alkynyl in each case optionally substituted by fluorine, chlorine-substituted C 3 -C 6 -cycloalkyl, in each case optionally monosubstituted to trisubstituted by fluorine, chlorine, bromine, C) -C 6 -alkyl, CpC 6 -
- M 2B is preferably oxygen or -S (O) 1n -.
- R 6B preferably represents in each case optionally fluorine- and / or chlorine-substituted C 1 -
- L 1B and L 3B or L 1B and L 2B together preferably each form an optionally substituted by fluorine and / or C r C 2 alkyl substituted 5- to 6-membered ring, which may optionally be interrupted by one or two oxygen atoms.
- X B particularly preferably represents chlorine, bromine and iodine.
- R 1B , R 2B and R 3B independently of one another particularly preferably represent hydrogen or
- M IB particularly preferably represents achiral C 1 -C 6 -alkylene, achiral C 3 -C 6 -alkenylene or achiral C 3 -C 6 -alkynylene.
- Q B particularly preferably represents hydrogen, fluorine, chlorine, cyano, trifluoromethyl, C 3 -C 6 -cycloalkyl or the group ' ⁇ .
- T B particularly preferably represents oxygen or -S (O) O 1 -.
- R 4B particularly preferably represents hydrogen, in each case optionally monosubstituted to trisubstituted by fluorine and / or chlorine, dQ-alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl or
- k is more preferably 1, 2 or 3.
- n is more preferably 0, 1 or 2.
- L 1B and L 3B independently of one another particularly preferably represent hydrogen, fluorine, chlorine, bromine, iodine, cyano, C 1 -C 4 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 4 -alkoxy, C 1 - C 2 haloalkoxy, in each case optionally mono- to disubstituted by fluorine, chlorine, bromine, C 1 -C 4 -alkyl,
- L 2B particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, in each case optionally monosubstituted to trisubstituted by fluorine and / or chlorine, C 1 -C 0 -. .2B 6B
- Alkyl C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl or for the group M ⁇ .
- M 2B is particularly preferably oxygen or -S (O) n , -.
- R 6B particularly preferably represents in each case optionally monosubstituted to thirteen times by fluorine and / or chlorine-substituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C 3 -C 6 -cycloalkyl, in each case optionally once to twice by fluorine, chlorine, bromine, C r
- X B is most preferably iodine.
- R 1B and R 2B are very particularly preferably hydrogen.
- RRR 3B most preferably represents the group ⁇ .
- M IB is very particularly preferably -C (CH 3 ) 2 CH 2 - or -C (C 2 Hj) 2 CH 2 -.
- Q B is very particularly preferably hydrogen, fluorine, chlorine, cyano, trifluoromethyl, C 3 - T 5_ R 4B
- T B is very particularly preferably -S-, -SO- or -SOR-.
- R 4B very particularly preferably represents in each case optionally monosubstituted to trisubstituted by fluorine and / or chlorine methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-
- L 1B and L 3B are very particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, methoxy, ethoxy, trifluoromethyl, difluoromethoxy or trifluoromethoxy.
- L 2B is very particularly preferably hydrogen. Fluorine. Chlorine. Bromine. Iodine. Cvano. for methyl, ethyl, n-propyl, iso-propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, allyl, butenyl M ?, which is optionally monosubstituted to monosubstituted by fluorine and / or chlorine.
- M 2B is most preferably oxygen or sulfur.
- R 6B very particularly preferably represents in each case optionally mono- to trisubstituted by fluorine and / or chlorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, allyl, butenyl or isoprenyl, optionally mono- to disubstituted by fluorine, chlorine, bromine, methyl, ethyl, methoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, cyano or nitro-substituted phenyl.
- All compounds according to the invention are already known as agents for controlling animal pests, in particular insects, and can be prepared by methods described in the prior art.
- the effectiveness of these compounds is good, but not always fully satisfactory especially at low rates and concentrations. There is therefore a need for an increase in the effectiveness of the compounds containing plant protection products.
- the active compounds can be used in the compositions according to the invention in a wide concentration range.
- concentration of the active ingredients in the formulation is usually 0.1-50 wt .-%.
- ammonium sulfate as a formulation aid is described for certain active ingredients and applications (WO 92/16108), but it is there to stabilize the formulation, not to increase the effect.
- the present invention thus relates to the use of ammonium and / or phosphonium salts to increase the efficacy of plant protection products containing insecticidally active agonists of the ryanodine receptor as an active ingredient.
- the invention also relates to compositions containing such insecticides and the activity-enhancing ammonium and / or phosphonium salts, both formulated active ingredients and ready-to-use agents (spray liquors).
- the subject matter of the invention is the use of these agents for controlling harmful insects.
- Ammonium and phosphonium salts which, according to the invention, increase the action of pesticides containing phthalic diamides are defined by formula (II)
- D is nitrogen or phosphorus
- D is preferably nitrogen
- R 4 , R 5 , R 6 and R 7 independently of one another represent hydrogen or in each case optionally substituted CpCg-alkyl or mono- or polyunsaturated, optionally substituted C 1 -C 4 -alkyl or Cg-alkylene, wherein the substituents can be selected from halogen, nitro and cyano,
- R 4 , R 5 , R 6 and R 7 are preferably each independently hydrogen or in each case optionally substituted Ci-Q-alkyl, wherein the substituents may be selected from halogen, nitro and cyano,
- R 4 , R 5 , R 6 and R 7 more preferably independently of one another are hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl or t-butyl,
- R 4 , R 5 , R 6 and R 7 most preferably represent hydrogen
- R 4 , R 5 , R 6 and R 7 furthermore very particularly preferably simultaneously represent methyl or simultaneously ethyl
- n 1, 2, 3 or 4
- n is preferably 1 or 2
- R 8 represents an inorganic or organic anion
- R 8 is preferred for hydrogencarbonate, tetraborate, fluoride, bromide, iodide, chloride, monohydrogenphosphate, dihydrogenphosphate, hydrogensulphate, tartrate, sulphate, nitrate, thiosulphate, thiocyanate, formate, lactate, acetate, propionate, butyrate, pentanoate, citrate or Oxalate stands,
- R 8 furthermore preferably represents carbonate, pentaborate, sulfite, benzoate, hydrogen oxalate, hydrogen citrate, methyl sulfate or tetrafluoroborate,
- R 8 particularly preferably represents lactate, sulfate, nitrate, thiosulfate, thiocyanate, citrate, oxalate or formate,
- R 8 is also particularly preferred for monohydrogen phosphate or dihydrogen phosphate
- R 8 very particularly preferably represents sulfate.
- the ammonium and phosphonium salts of the formula (II) can be used in a wide concentration range for increasing the effect of crop protection agents containing ketoenols.
- the ammonium and / or phosphonium salt concentration in the formulation is selected to be in the specified general, preferred or most preferred ranges after dilution of the formulation to the desired drug concentration.
- the concentration of the salt in the formulation is usually 1-50% by weight.
- a penetration promoter is added to the crop protection agents to increase the effect. It can be described as completely surprising that even in these cases an even greater increase in activity can be observed.
- the subject matter of the present invention is therefore likewise the use of a combination of penetration promoters and ammonium and / or phosphonium salts for increasing the efficacy of pesticides which contain insecticidally active phthalic diamides as active ingredient.
- the invention also relates to compositions containing insecticidally active phthalic diamides, penetration promoters and ammonium and / or phosphonium salts, both formulated active ingredients and ready-to-use agents (spray liquors).
- the subject matter of the invention is the use of these agents for controlling harmful insects.
- Suitable penetration promoters in the present context are all those substances which are usually used to improve the penetration of agrochemical active substances into plants.
- Penetration promoters are in this context defined by the fact that they can penetrate from the aqueous spray mixture and / or from the spray coating in the cuticle of the plant and thereby increase the material mobility (mobility) of active ingredients in the cuticle.
- the method described in the literature can be used to determine this property.
- Suitable penetration promoters are, for example, alkanol alkoxylates.
- Penetration promoters according to the invention are alkanol alkoxylates of the formula
- R is straight-chain or branched alkyl having 4 to 20 carbon atoms
- R ' is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl or n-hexyl
- AO stands for an ethylene oxide radical, a propylene oxide radical, a butylene oxide radical or mixtures of ethylene oxide and propylene oxide radicals or butylene oxide radicals and
- v stands for numbers from 2 to 30.
- a preferred group of penetration promoters are alkanol alkoxylates of the formula
- n stands for numbers from 2 to 20.
- Another preferred group of penetration promoters are alkanol alkoxylates of the formula
- EO is -CH 2 -CH 2 -O-
- q stands for numbers from 1 to 10.
- Another preferred group of penetration promoters are alkanol alkoxylates of the formula
- EO stands for -CH 2 -CH 2 -O-
- PO is CH-CH-O ;
- s stands for numbers from 1 to 10.
- Another preferred group of penetration enhancers are alkanol alkoxylates of the formula
- EO is CH 2 -CH 2 -O-
- q stands for numbers from 1 to 10.
- Another preferred group of penetration promoters are alkanol alkoxylates of the formula
- EO is CH 2 -CH 2 -O-
- s stands for numbers from 1 to 10.
- Another preferred group of penetration promoters are alkanol alkoxylates of the formula
- u stands for numbers from 6 to 17.
- R is preferably butyl, isobutyl, n-pentyl, i-pentyl, neopentyl, n-hexyl, i-hexyl, n-octyl, i-octyl, 2-ethylhexyl, nonyl, i-nonyl, decyl, n Dodecyl, i-dodecyl, lauryl, myristyl, i-tridecyl, trimethyl-nonyl, palmityl, stearyl or eicosyl.
- alkanol alkoxylate of the formula (III-c) is 2-ethyl-hexyl alkoxylate of the formula
- EO stands for -CH 2 -CH 2 -O-
- the numbers 8 and 6 represent average values called.
- EO is CH 2 -CH 2 -O-
- the numbers 10, 6 and 2 represent average values called.
- Particularly preferred alkanol alkoxylates of the formula (III-f) are compounds of this formula in which
- alkanol alkoxylate of the formula (III-f-1) very particular preference is given to alkanol alkoxylate of the formula (III-f-1)
- u stands for the average 8.4.
- alkanol alkoxylates are generally defined by the above formulas. These substances are mixtures of substances of the specified type with different chain lengths. For the indices, therefore, average values are calculated, which can also differ from whole numbers.
- alkanol alkoxylates of the formulas given are known and are partly available commercially or can be prepared by known methods (compare WO 98/35 553, WO 00/35 278 and EP-A 0 681 865).
- Suitable penetration promoters include, for example, substances which promote the solubility of the compounds of the formula (I) in the spray coating. These include, for example, mineral or vegetable oils. Suitable oils are all mineral or vegetable oils which may be used in agrochemical compositions, optionally modified oils. exemplary may be mentioned sunflower oil, rapeseed oil, olive oil, castor oil, rapeseed oil, corn oil, cottonseed oil and soybean oil or the esters of said oils. Rape oil, sunflower oil and their methyl or ethyl esters are preferred.
- the concentration of penetration promoter can be varied in the agents according to the invention in a wide range. In the case of a formulated crop protection agent, it is generally from 1 to 95% by weight, preferably from 1 to 55% by weight, more preferably from 15 to 40% by weight. In the ready-to-use agents (spray liquors), the concentration is generally between 0.1 and 10 g / l, preferably between 0.5 and 5 g / l.
- Plant protection agents according to the invention may also contain further components, for example surfactants or dispersants or emulsifiers.
- Suitable nonionic surfactants or dispersing agents are all substances of this type which can usually be used in agrochemical compositions.
- Suitable anionic surfactants are all substances of this type conventionally usable in agrochemical compositions. Preference is given to alkali metal and alkaline earth metal salts of alkyl sulfonic acids or alkylaryl sulfonic acids.
- anionic surfactants or dispersing agents are salts of polystyrenesulfonic acids which are sparingly soluble in vegetable oil, salts of polyvinylsulfonic acids, salts of naphthalenesulfonic acid-formaldehyde condensation products, salts of condensation products of naphthalenesulfonic acid, phenolsulfonic acid and formaldehyde and salts of lignosulfonic acid.
- Suitable additives which may be present in the formulations according to the invention are emulsifiers, foam-inhibiting agents, preservatives, antioxidants, dyes and inert fillers.
- Preferred emulsifiers are ethoxylated nonylphenols, reaction products of alkylphenols with ethylene oxide and / or propylene oxide, ethoxylated arylalkylphenols, furthermore ethoxylated and propoxylated arylalkylphenols, and sulfated or phosphated arylalkyl ethoxylates or ethoxy-propoxylates, sorbitan derivatives such as polyethylene oxide sorbitan fatty acid esters and sorbitan Fatty acid esters, may be mentioned as examples.
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- 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
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102005059466A DE102005059466A1 (en) | 2005-12-13 | 2005-12-13 | Insecticidal compositions having improved activity |
PCT/EP2006/011473 WO2007068357A1 (en) | 2005-12-13 | 2006-11-30 | Insecticidal compositions having improved effect |
Publications (1)
Publication Number | Publication Date |
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EP1962595A1 true EP1962595A1 (en) | 2008-09-03 |
Family
ID=37882302
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP06829188A Withdrawn EP1962595A1 (en) | 2005-12-13 | 2006-11-30 | Insecticidal compositions having improved effect |
Country Status (9)
Country | Link |
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US (1) | US20080319081A1 (en) |
EP (1) | EP1962595A1 (en) |
JP (1) | JP2009519260A (en) |
KR (1) | KR20080076983A (en) |
CN (1) | CN101325873A (en) |
AU (1) | AU2006326730A1 (en) |
BR (1) | BRPI0619814A2 (en) |
DE (1) | DE102005059466A1 (en) |
WO (1) | WO2007068357A1 (en) |
Families Citing this family (8)
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---|---|---|---|---|
DE10330724A1 (en) * | 2003-07-08 | 2005-01-27 | Bayer Cropscience Ag | Drug combinations with insecticidal and acaricidal properties |
DE102004035134A1 (en) * | 2004-07-20 | 2006-02-16 | Bayer Cropscience Ag | Selective insecticides based on Halogenalkylnicotinsäurederivaten, Anthranilsäureamiden or phthalic diamides and safeners |
KR20070054700A (en) * | 2004-08-31 | 2007-05-29 | 바이엘 크롭사이언스 아게 | Optically active phthalamides |
BRPI0717153A2 (en) * | 2006-09-30 | 2013-10-15 | Bayer Cropscience Ag | IMPROVEMENT OF THE BIOLOGICAL ACTION OF AGROCHEMICAL COMPOSITIONS ON THE APPLICATION TO THE SUBSTRATE OF CROPS, PROPER FORMULATIONS AND THEIR APPLICATION |
EP2123159A1 (en) | 2008-05-21 | 2009-11-25 | Bayer CropScience AG | (1,2-Benzisothiazol-3-yl)(thio)carbamates and (1,2-Benzisothiazol-3-yl)(thio)oxamates and their oxidation forms as pesticides |
EP2196461A1 (en) | 2008-12-15 | 2010-06-16 | Bayer CropScience AG | 4-Amino-1,2,3-benzoxathiazine-derivatives as pesticides |
KR20160148046A (en) | 2008-12-18 | 2016-12-23 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | Tetrazole substituted anthranilic amides as pesticides |
GB0907003D0 (en) * | 2009-04-23 | 2009-06-03 | Syngenta Ltd | Formulation |
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- 2005-12-13 DE DE102005059466A patent/DE102005059466A1/en not_active Withdrawn
-
2006
- 2006-11-30 KR KR1020087015890A patent/KR20080076983A/en not_active Application Discontinuation
- 2006-11-30 BR BRPI0619814-7A patent/BRPI0619814A2/en not_active IP Right Cessation
- 2006-11-30 CN CNA2006800467224A patent/CN101325873A/en active Pending
- 2006-11-30 AU AU2006326730A patent/AU2006326730A1/en not_active Abandoned
- 2006-11-30 EP EP06829188A patent/EP1962595A1/en not_active Withdrawn
- 2006-11-30 JP JP2008544799A patent/JP2009519260A/en not_active Withdrawn
- 2006-11-30 US US12/096,179 patent/US20080319081A1/en not_active Abandoned
- 2006-11-30 WO PCT/EP2006/011473 patent/WO2007068357A1/en active Application Filing
Non-Patent Citations (1)
Title |
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See references of WO2007068357A1 * |
Also Published As
Publication number | Publication date |
---|---|
US20080319081A1 (en) | 2008-12-25 |
CN101325873A (en) | 2008-12-17 |
BRPI0619814A2 (en) | 2011-10-18 |
AU2006326730A1 (en) | 2007-06-21 |
DE102005059466A1 (en) | 2007-06-14 |
KR20080076983A (en) | 2008-08-20 |
WO2007068357A1 (en) | 2007-06-21 |
JP2009519260A (en) | 2009-05-14 |
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