MX2008007620A - Insecticidal compositions having improved effect - Google Patents
Insecticidal compositions having improved effectInfo
- Publication number
- MX2008007620A MX2008007620A MXMX/A/2008/007620A MX2008007620A MX2008007620A MX 2008007620 A MX2008007620 A MX 2008007620A MX 2008007620 A MX2008007620 A MX 2008007620A MX 2008007620 A MX2008007620 A MX 2008007620A
- Authority
- MX
- Mexico
- Prior art keywords
- alkyl
- optionally
- substituted
- hydrogen
- optionally substituted
- Prior art date
Links
- 230000000694 effects Effects 0.000 title claims abstract description 34
- 239000000203 mixture Substances 0.000 title claims description 71
- 230000000749 insecticidal Effects 0.000 title claims description 21
- 230000035515 penetration Effects 0.000 claims abstract description 51
- 125000004122 cyclic group Chemical class 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 228
- 229910052739 hydrogen Inorganic materials 0.000 claims description 142
- 239000001257 hydrogen Substances 0.000 claims description 142
- 150000002431 hydrogen Chemical group 0.000 claims description 107
- 125000003545 alkoxy group Chemical group 0.000 claims description 90
- 239000000460 chlorine Substances 0.000 claims description 84
- 229910052801 chlorine Inorganic materials 0.000 claims description 82
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 80
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 80
- 239000011737 fluorine Substances 0.000 claims description 70
- 229910052731 fluorine Inorganic materials 0.000 claims description 70
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 68
- 229910052736 halogen Inorganic materials 0.000 claims description 66
- 150000002367 halogens Chemical class 0.000 claims description 66
- 229910052760 oxygen Inorganic materials 0.000 claims description 66
- 239000001301 oxygen Substances 0.000 claims description 66
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 66
- 229910052799 carbon Inorganic materials 0.000 claims description 62
- 150000001875 compounds Chemical class 0.000 claims description 59
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 57
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 57
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 56
- 229910052717 sulfur Inorganic materials 0.000 claims description 56
- 239000011593 sulfur Substances 0.000 claims description 56
- 125000001188 haloalkyl group Chemical group 0.000 claims description 54
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 53
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 47
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 45
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 42
- -1 slkoxysyl Chemical group 0.000 claims description 40
- 125000003342 alkenyl group Chemical group 0.000 claims description 39
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 39
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 36
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
- 125000001424 substituent group Chemical group 0.000 claims description 30
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 28
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 27
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 23
- 239000011780 sodium chloride Substances 0.000 claims description 23
- 125000004414 alkyl thio group Chemical group 0.000 claims description 21
- 125000004429 atoms Chemical group 0.000 claims description 20
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 19
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 claims description 18
- 239000011630 iodine Chemical group 0.000 claims description 18
- 229910052740 iodine Inorganic materials 0.000 claims description 18
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 18
- NBIIXXVUZAFLBC-UHFFFAOYSA-L phosphate Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 claims description 18
- 239000007921 spray Substances 0.000 claims description 17
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 17
- 125000005842 heteroatoms Chemical group 0.000 claims description 16
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 15
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 15
- 239000004480 active ingredient Substances 0.000 claims description 14
- 125000000304 alkynyl group Chemical group 0.000 claims description 13
- 125000004076 pyridyl group Chemical group 0.000 claims description 13
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 11
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims description 11
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 125000004430 oxygen atoms Chemical group O* 0.000 claims description 9
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 150000002500 ions Chemical class 0.000 claims description 8
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-M methanoate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- MUBZPKHOEPUJKR-UHFFFAOYSA-L oxalate Chemical compound [O-]C(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-L 0.000 claims description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
- 125000000335 thiazolyl group Chemical group 0.000 claims description 8
- 239000002917 insecticide Substances 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
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 6
- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N oxane Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 6
- 238000010298 pulverizing process Methods 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000001425 triazolyl group Chemical group 0.000 claims description 6
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 6
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 5
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 5
- 125000004492 methyl ester group Chemical group 0.000 claims description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 239000008158 vegetable oil Substances 0.000 claims description 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
- 241001454295 Tetranychidae Species 0.000 claims description 4
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 239000002480 mineral oil Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000004434 sulfur atoms Chemical group 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 3
- 241000238631 Hexapoda Species 0.000 claims description 3
- 241001414987 Strepsiptera Species 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 claims description 2
- 239000005664 Spirodiclofen Substances 0.000 claims description 2
- 102100014526 TBC1D8 Human genes 0.000 claims description 2
- 101710035852 TBC1D8 Proteins 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 150000001449 anionic compounds Chemical class 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-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
- 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
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-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
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims description 2
- 150000002891 organic anions Chemical class 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- DTDSAWVUFPGDMX-UHFFFAOYSA-N spirodiclofen Chemical compound CCC(C)(C)C(=O)OC1=C(C=2C(=CC(Cl)=CC=2)Cl)C(=O)OC11CCCCC1 DTDSAWVUFPGDMX-UHFFFAOYSA-N 0.000 claims description 2
- 125000004354 sulfur functional group Chemical group 0.000 claims description 2
- 229940095064 tartrate Drugs 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- ODGCEQLVLXJUCC-UHFFFAOYSA-N tetrafluoroborate Chemical compound F[B-](F)(F)F ODGCEQLVLXJUCC-UHFFFAOYSA-N 0.000 claims description 2
- 150000003568 thioethers Chemical class 0.000 claims description 2
- 241001438449 Silo Species 0.000 claims 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 239000003961 penetration enhancing agent Substances 0.000 claims 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
- 102200018929 ACOT2 R16S Human genes 0.000 claims 2
- 102200031660 CHCHD10 R15S Human genes 0.000 claims 2
- 210000001161 Embryo, Mammalian Anatomy 0.000 claims 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 2
- 235000010446 mineral oil Nutrition 0.000 claims 2
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- 102220436388 DNAJC5B R17S Human genes 0.000 claims 1
- 102200159759 LILRB4 R18S Human genes 0.000 claims 1
- 102200029950 MERTK R20S Human genes 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 238000004806 packaging method and process Methods 0.000 claims 1
- 229920001281 polyalkylene Polymers 0.000 claims 1
- 102220264985 rs182760732 Human genes 0.000 claims 1
- 150000004072 triols Chemical group 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 abstract description 21
- 150000004714 phosphonium salts Chemical class 0.000 abstract description 19
- 230000000875 corresponding Effects 0.000 abstract description 6
- 108009000552 Fatty Acid Biosynthesis Proteins 0.000 abstract description 3
- 239000003112 inhibitor Substances 0.000 abstract description 3
- 230000002401 inhibitory effect Effects 0.000 abstract description 3
- 239000003623 enhancer Substances 0.000 abstract 1
- 230000002708 enhancing Effects 0.000 abstract 1
- 239000011814 protection agent Substances 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 47
- 239000003995 emulsifying agent Substances 0.000 description 21
- CBXCPBUEXACCNR-UHFFFAOYSA-N Tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 20
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 19
- 230000000895 acaricidal Effects 0.000 description 17
- 230000002363 herbicidal Effects 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 13
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M isothiocyanate Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 13
- VWSRWGFGAAKTQG-UHFFFAOYSA-N Ammonium benzoate Chemical compound [NH4+].[O-]C(=O)C1=CC=CC=C1 VWSRWGFGAAKTQG-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 229940090948 ammonium benzoate Drugs 0.000 description 11
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 11
- 238000004166 bioassay Methods 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 9
- 235000011130 ammonium sulphate Nutrition 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- KRKNYBCHXYNGOX-UHFFFAOYSA-K 2qpq Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 7
- VZTDIZULWFCMLS-UHFFFAOYSA-N Ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 7
- BFNBIHQBYMNNAN-UHFFFAOYSA-N Ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 239000012141 concentrate Substances 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 241001124076 Aphididae Species 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 6
- 229940001447 Lactate Drugs 0.000 description 6
- 241000721621 Myzus persicae Species 0.000 description 6
- BWKOZPVPARTQIV-UHFFFAOYSA-N azanium;hydron;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [NH4+].OC(=O)CC(O)(C(O)=O)CC([O-])=O BWKOZPVPARTQIV-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 238000000053 physical method Methods 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- PQUCIEFHOVEZAU-UHFFFAOYSA-N Ammonium sulfite Chemical compound [NH4+].[NH4+].[O-]S([O-])=O PQUCIEFHOVEZAU-UHFFFAOYSA-N 0.000 description 5
- 240000002791 Brassica napus Species 0.000 description 5
- 235000006008 Brassica napus var napus Nutrition 0.000 description 5
- 238000007792 addition Methods 0.000 description 5
- MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 description 5
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 4
- PRKQVKDSMLBJBJ-UHFFFAOYSA-N Ammonium carbonate Chemical compound N.N.OC(O)=O PRKQVKDSMLBJBJ-UHFFFAOYSA-N 0.000 description 4
- DVARTQFDIMZBAA-UHFFFAOYSA-O Ammonium nitrate Chemical compound [NH4+].[O-][N+]([O-])=O DVARTQFDIMZBAA-UHFFFAOYSA-O 0.000 description 4
- 241001600408 Aphis gossypii Species 0.000 description 4
- 235000002566 Capsicum Nutrition 0.000 description 4
- 240000004160 Capsicum annuum Species 0.000 description 4
- 235000002567 Capsicum annuum Nutrition 0.000 description 4
- 241000721623 Myzus Species 0.000 description 4
- 239000006002 Pepper Substances 0.000 description 4
- 235000016761 Piper aduncum Nutrition 0.000 description 4
- 235000017804 Piper guineense Nutrition 0.000 description 4
- 240000000129 Piper nigrum Species 0.000 description 4
- 235000008184 Piper nigrum Nutrition 0.000 description 4
- 235000019484 Rapeseed oil Nutrition 0.000 description 4
- 239000003905 agrochemical Substances 0.000 description 4
- 239000001099 ammonium carbonate Substances 0.000 description 4
- 235000012501 ammonium carbonate Nutrition 0.000 description 4
- 239000001511 capsicum annuum Substances 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
- 238000009792 diffusion process Methods 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- 239000005695 Ammonium acetate Substances 0.000 description 3
- RZOBLYBZQXQGFY-UHFFFAOYSA-N Ammonium lactate Chemical compound [NH4+].CC(O)C([O-])=O RZOBLYBZQXQGFY-UHFFFAOYSA-N 0.000 description 3
- 239000004251 Ammonium lactate Substances 0.000 description 3
- VBIXEXWLHSRNKB-UHFFFAOYSA-N Ammonium oxalate Chemical compound [NH4+].[NH4+].[O-]C(=O)C([O-])=O VBIXEXWLHSRNKB-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-L Sulphite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 3
- 239000000642 acaricide Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000005108 alkenylthio group Chemical group 0.000 description 3
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- USFZMSVCRYTOJT-UHFFFAOYSA-N ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 3
- 229940043376 ammonium acetate Drugs 0.000 description 3
- 235000019257 ammonium acetate Nutrition 0.000 description 3
- 229940059265 ammonium lactate Drugs 0.000 description 3
- 235000019286 ammonium lactate Nutrition 0.000 description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000004009 herbicide Substances 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QBDAFARLDLCWAT-UHFFFAOYSA-N 2,3-dihydropyran-6-one Chemical class O=C1OCCC=C1 QBDAFARLDLCWAT-UHFFFAOYSA-N 0.000 description 2
- YYCQUUTYXPMBLY-UHFFFAOYSA-N 3-phenylpyran-2-one Chemical class O=C1OC=CC=C1C1=CC=CC=C1 YYCQUUTYXPMBLY-UHFFFAOYSA-N 0.000 description 2
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- 239000001166 ammonium sulphate Substances 0.000 description 2
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- 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
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- 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
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- 229940042399 direct acting antivirals Protease inhibitors Drugs 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 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 1
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- VEWLDLAARDMXSB-UHFFFAOYSA-N ethenyl sulfate;hydron Chemical compound OS(=O)(=O)OC=C VEWLDLAARDMXSB-UHFFFAOYSA-N 0.000 description 1
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- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
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- 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
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- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical class O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 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
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- 239000007858 starting material Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Abstract
The invention relates to plant protection agents which contain inhibitors of fatty acid biosynthesis (for example phenyl-substituted cyclic ketoenols). The aim of the invention is to increase their effect by adding ammonium salts and/or phosphonium salts or by adding ammonium salts or phosphonium salts and penetration enhancers. The invention also relates to corresponding products, to methods for producing them and to their use in plant protection.
Description
INSECTICIDES COMPOSITIONS WITH IMPROVED EFFECT
DESCRIPTION OF THE INVENTION The present invention relates to the increase of the effect of phytosanitary products containing inhibitors of the fatty acid biosynthesis, especially cyclic ketoenols substituted with phenyl, by the addition of ammonium or phosphonium salts and optionally penetration facilitators, to the corresponding agents, to procedures for their preparation and their use in phytosanitary protection, especially as insecticides and / or acaricides. Pharmaceutical properties of 3-acyl-pyrrolidin-2,4-diones were previously described (S. Suzuki et al., Chem. Pharm. Bull., 1120 (1967)). In addition, N-phenylpyrrolidin-2,4-diones were synthesized by R. Schmierer and H. Mildenberger (Liebigs Ann. Chem. 1985, 1095). No biological activity of these compounds was described. EP-A-0 262 399 and GB-A-2 266 888 disclose compounds of similar structure (3-aryl-pyrrolidin-2,4-diones), of which, however, no effect has been known. any herbicide, insecticide or acaricide. Bicyclic 3-aryl-pyrrolidin-2,4-dione derivatives unsubstituted with herbicidal, insecticidal or acaricidal effect are known.
(EP-A-355 599, EP-A-415 211 and JP-A-12-053 670) as well as monocyclic 3-aryl-pyrrolidin-2,4-dione derivatives REF. : 193778
substituted (EP-A-377 893 and EP-A-442 077). Furthermore, derivatives of polycyclic 3-arylpyrrolidin-2,4-dione (EP-A-442 073) as well as lH-arylpyrrolidinedione derivatives are known (EP-A-456 063, EP-A-521 334, EP -A-596 298, EP-A-613 884, EP-A-613 885, WO 95/01 997, WO 95/26 954, WO 95/20 572, EP-A-0 668 267, WO 96/25 395, WO 96/35 664, WO 97/01 535, WO 97/02 243, WO 97/36 868, WO 97/43275, WO 98/05638, WO 98/06721, WO 98/25928, WO 99/16748. , WO 99/24437, WO 99/43649, WO 99/48869 and WO 99/55673, WO 01/17972, WO 01/23354, WO 01/74770, WO 03/013249, WO 04/007448, WO 04/024688. , WO 04/065366, WO 04/080962, WO 04/111042, WO 05/044791, WO 05/044796, WO 05/048710, WO 05/049569, WO 05/066125, WO 05/092897, WO 06/000355 , WO 06/029799, WO 06/056281, WO 06/056282, WO 06/089633). It is known that certain substituted γ-dihydrofuran-2-one derivatives possess herbicidal properties (see DE-A-4 014 420). The syntheses of the tetronic acid derivatives used as starting compounds (such as, for example, 3- (2-methyl-phenyl) -4-hydroxy-5- (4-fluorophenyl) -? - ^ - dihydrofuranone- ( 2)) is also described in DE-A-4 014 420. Compounds of similar structure without indication of an insecticidal and / or acaricidal activity are known from the publication of Campbell et al., J. Chem. Soc., Perkin Trans.
1, 1985, (8) 1567-76. In addition, 3-aryl derivatives are known
? ^ - dihydrofuranone with herbicidal, acaricidal and insecticidal properties of EP-A-528 156, EP-A-0 647 637, WO 95/26 345, WO 96/20 196, WO 96/25 395, WO 96 / 35 664, WO 97/01 535, WO 97/02 243, WO 97/36 868, WO 98/05638, WO 98/25928, WO 99/16748, WO 99/43649, WO 99/48869, WO 99/55673 , WO 01/17972, WO 01/23354, WO 01/74770, WO 03/013 249, WO 04/024 688, WO 04/080 962, WO 04/111 042, WO 05/092897, WO 06/000355, WO 06/029799 and WO 06/089633. Derivatives of 3-aryl-3-dihydrothiophenone are also known (WO 95/26 345, 96/25 395, WO 97/01 535, WO 97/02 243, WO 97/36 868, WO 98/05638 , WO 98/25928, WO 99/16748, WO 99/43649, WO 99/48869, WO 99/55673, WO 01/17772, WO 01/23354, WO 01/74770, WO 03/013249, WO 04/080. 962, WO 04/111 042, WO 05/092897, WO 06/029799). Certain unsubstituted phenyl-pyrone derivatives in the phenyl ring have already been described (see AM Chirazi, T. Kappe and E. Ziegler, Arch. Pharm. 309, 558 (1976) and K.-H. Boltze and K. Heidenbluth, Chem. Ber. 9JL, 2849), where a potential utility as pesticides is not indicated for these compounds. As for substituted phenyl pyrone derivatives on the phenyl ring with herbicidal, acaricidal and insecticidal properties are described in EP-A-588 137, WO 96/25 395, WO 96/35 664, WO 97/01 535 , WO 97/02 243, WO 97/16 436, WO 97/19 941, WO 97/36 868, WO 98/05638, WO
-
99/43649, WO 99/48869, WO 99/55673, WO 01/17972, WO 01/74770, WO 03/013249, WO 04/080 962, WO 04/111 042, WO 05/092897, WO 06/029799. . Certain unsubstituted 5-phenyl-1, 3-thiazine derivatives in the phenyl ring have already been described (see E. Ziegler and E. Steiner, Monatsh 95, 147 (1964), R. Ketcham, T. Kappe and E. Ziegler, J. Heterocycl, Chem. 1_0, 223 (1973)), where a possible utility as parasite-fighting agents is not indicated for these compounds. As for 5-phenyl-1, 3-thiazine derivatives substituted on the phenyl ring with herbicidal, acaricidal and insecticidal effect are described in WO 94/14 785, WO 96/02 539, WO 96/35 664, WO 97/01 535, WO 97/02 243, WO 97/02 243, WO 97/36 868, WO 99/05638, WO 99/43649, WO 99/48869, WO 99/55673, WO 01/17972, WO 01/74770, WO 03/013249, WO 04/080 962, WO 04/111 042, WO 05/092897 and WO 06/029799. It is known that certain substituted 2-arylcyclopentandiones have herbicidal, insecticidal and acaricidal properties (see, for example, US-4 283 348, 4 338 122, 4 436 666, 4 526 723, 4 551 547, 4 632 698; 96/01 798, WO 96/03 366, WO 97/14 667 as well as WO 98/39281, WO 99/43649, WO 99/48869, WO 99/55673, WO 01/17972, WO 01/74770, WO 03 / 013249, WO 04/080 962, WO 04/111 042, WO 05/092897 and WO 06/029799). In addition, similarly substituted compounds are known; 3-hydroxy-5, 5-dimethyl-2-phenylcyclopent-2-en-l-one of
- the publication by Micklefield et al., Tetrahedron, (1992), 7519-26 as well as the natural substance invitutin (-) - cis-5- (3,4-dihydroxyphenyl) -3,4-dihydroxy-2- (4 -hydroxyphenyl) -cyclo-pent-2-en-one from the publication of Edwards et al., J. Chem. Soc. S, (1967), 405-9. No insecticidal or acaricidal effect is described. Furthermore, 2- (2,, 6-trimethylphenyl) -1,3-indandione of the publication J. Economic Entomology, 66, (1973), 584 and of the publication for patent application information DE-A 2 361 084 are known. , with indications of herbicidal and acaricidal effects. It is known that certain substituted 2-arylcyclohexanediones have herbicidal, insecticidal and acaricidal properties (US Pat. Nos. 4 175 135, 4 209 432, 4 256 657, 4 256 658, 4 256 659, 4 257 858, 4 283 348, 4 303 669 , 4 351 666, 4 409 153, 4 436 666, 4 526 723, 4 613 617, 4 659 372, DE-A 2 813 341, as well as Wheeler, TN, J. Org. Chem. 4_4, 4906 (1979) ), WO 99/43649, WO 99/48869, WO 99/55673, WO 01/17972, WO 01/74770, WO 03/013249, WO 04/080 962, WO 04/111 042, WO 05/092897 and WO 06/029799). It is known that certain substituted 4-aryl-pyrazolidin-3, 5-diones possess acaricidal, insecticidal and herbicidal properties (see, for example, WO 92/16 510, EP-A-508 126, WO 96/11 574, WO 96/21 652, WO 99/47525, WO 01/17 351, WO 01/17 352, WO 01/17 353, WO 01/17 972, WO 01/17 973, WO 03/028 466, WO 03 / 062 244, WO 04/080 962, WO 04/111
-
042, WO 05/005428, WO 05/016873, WO 05/092897 and WO 06/029799). It is known that certain tetrahydropyridones possess herbicidal properties (JP 0832530). In addition, special 4-hydroxytetrahydropyridones with acaricidal, insecticidal and herbicidal properties are known (JP 11152273). 4-hydroxy-tetrahydropyridones were also known as parasite and herbicide control agents of WO 01/79204. It is known that certain derivatives of 5,6-dihydropyrone have antiviral properties as protease inhibitors
(WO 95/14012). In addition, 4-phenyl-6- (2-phenethyl) -5,6-dihydropyrone is known from the synthesis of cavalactone derivatives (Kappe et al., Arch. Pharm. 309, 558-564 (1976)).
In addition, 5,6-dihydropyrone derivatives are known as intermediates (White, J.D., Brenner, J.B., Deinsdale, M.J., J. Amer. Chem. Soc. 93, 281-282 (1971)). Derivatives of 3-phenyl-5,6-dihydropyrone are described with applications in phytosanitary protection in WO 01/98288. All the active principles contained in the agents according to the invention are already known and can be prepared according to procedures described in the state of the art
(see references cited above). Its effect is good, however especially in small amounts of use and concentrations it is not always completely satisfactory. Furthermore, the compatibility with plants of these compounds does not
It is always enough. There is therefore a need for an increase in the effect of the compounds contained in plant protection products. In the literature it was already described that the effect of different active principles can be increased by the addition of ammonium salts. In this respect, however, it is a matter of salts acting as detergents (for example, WO 95/017817) or salts with long alkyl and / or aryl substituents, which act to permeate or increase the solubility of the active principle (for example, EP-A 0 453 086, EP-A 0 664 081, FR-A 2 600 494, US 4 844 734, US 5 462 912, US 5 538 937, US-A 03/02 24939, US-A 05 / 0009880, US-A 05/0096386). Furthermore, the state of the art describes the effect only for certain active principles and / or certain applications of the corresponding agents. In many other cases it is salts of sulphonic acids, in which the acids act properly by paralyzing the insects
(US 2 842 476). An increase in the effect, for example, by means of ammonium sulphate is described, for example, for glyphosate and phosphinothricin herbicides (US 6 645 914, EP-A2 0 036 106). A corresponding effect on insecticides in this state of the art has not yet been disclosed in detail. The use of ammonium sulfate as an adjuvant for formulation for certain principles is also described
active ingredients and applications (WO 92/16108), but this serves for the stabilization of the formulation not for the increase of the effect. It has now been found quite surprisingly that the effect of insecticides and / or acaricides of the class of cyclic ketoenols substituted with phenyl can be clearly increased by the addition of ammonium or phosphonium salts to the application solution or by the incorporation of these salts to a formulation containing cyclic ketoenols substituted with phenyl. Therefore, the object of the present invention is the use of ammonium or phosphonium salts for the increase of the effect of phytosanitary products, containing cyclic ketoenols substituted with phenyl insecticidal and / or acaricidal effect as active principle. The invention also relates to agents containing cyclic ketoenols substituted with phenyl having an insecticidal and / or acaricidal effect and the ammonium or phosphonium salts which increase the effect, in particular both active ingredients formulated and ready-to-use agents (spray liquors). ). Finally, the use of these agents for the control of parasitic insects and / or spider mites is also object of the invention. Active principles according to the invention of the class of cyclic ketoenols, substituted with phenyl, the effect of which can be increased by the addition of ammonium salts or
of phosphonium to the active compound preparations formulated or ready for use are defined by formula (I),
wherein W is hydrogen, alkyl, alkenyl, alkynyl, halogen, alkoxy, haloalkyl, haloalkoxy or cyano, X is halogen, alkyl, alkenyl, alkynyl, alkoxy, alkoxy-alkoxy, haloalkyl, haloalkoxy or cyano, and is hydrogen, halogen , alkyl, alkenyl, alkynyl, alkoxy, cyano, haloalkyl, haloalkoxy or is phenyl or hetaryl each optionally substituted, Z is hydrogen, halogen, alkyl, haloalkyl, cyano, alkoxy or haloalkoxy, CKE represents one of the groups
,
-
wherein A is hydrogen, alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl each optionally substituted with halogen, saturated or unsaturated cycloalkyl, optionally substituted, wherein optionally at least one ring atom is replaced by a heteroatom, or is aryl , arylalkyl or hetaryl each optionally substituted with halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, cyano or nitro, B is hydrogen, alkyl or alkoxyalkyl, or A and B together with the carbon atom to which they are attached is a ring unsubstituted or substituted, saturated or unsaturated,
optionally containing at least one heteroatom, D is hydrogen or an optionally substituted radical of the group of alkyl, alkenyl, alkynyl, alkoxyalkyl, saturated or unsaturated cycloalkyl, wherein one or more ring members are optionally replaced by heteroatoms, arylalkyl, aryl , hetarylalkyl or hetaryl or A and D together with the atoms to which they are attached is a ring unsubstituted or substituted in part A, D, saturated or unsaturated and optionally containing at least one heteroatom (in the case of CKE = 8 one more), or
A and 0.1 together are alkenediyl or alkanediyl optionally substituted with hydroxy or each optionally substituted with alkyl, alkoxy, alkylthio, cycloalkyl, benzyloxy or aryl, or D and 00 together with the atoms to which they are attached are an unsubstituted ring or substituted in part A, Q1, saturated or unsaturated, and optionally containing at least one heteroatom, 00 is hydrogen, alkyl, alkoxyalkyl, optionally substituted cycloalkyl, (wherein optionally a methylene group is replaced by oxygen or sulfur) or optionally substituted phenyl, X, X, X and X are independently from each other hydrogen
or alkyl, Q3 is optionally substituted hydrogen, alkyl, alkoxyalkyl, alkylthioalkyl, optionally substituted cycloalkyl (in which a methylene group is optionally replaced by oxygen or sulfur) or optionally substituted phenyl, or Q_l and Q2 together with the carbon atom to which they are attached are an unsubstituted or substituted ring optionally containing a heteroatom, or Q3 and Q4 together with the carbon atom to which they are attached is an unsubstituted or substituted, saturated or unsaturated ring, optionally containing a heteroatom, G is hydrogen (a) or is one of the groups
wherein E is an equivalent of metal ion or an ammonium ion, L is oxygen or sulfur, M is oxygen or sulfur, R1 is alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl substituted each
one of them optionally with halogen, or cycloalkyl optionally substituted with halogen, alkyl or alkoxy, which may be interrupted with at least one heteroatom, or is phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl each optionally substituted, R 2 is alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl each optionally substituted with halogen or is cycloalkyl, phenyl or benzyl each optionally substituted, R ^, R4 and R5 are independently from each other alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio, cycloalkylthio substituted each of them optionally with halogen or are phenyl, benzyl, phenoxy or phenylthio each optionally substituted, R and X are independently of each other hydrogen, alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl each optionally substituted with halogen, optionally substituted phenyl, optionally substituted benzyl, or together with the N atom to which they are attached are a ring optionally interrupted with oxygen or
sulfur. The compounds of formula (I) can also be present, depending on the type of substituents, as geometrical and / or optical isomers or isomeric mixtures, in different compositions, which can optionally be separated in the usual manner and manner. Both the pure isomers and also the isomeric mixtures are agents according to the invention that can be used and their effect can be increased by ammonium or phosphonium salts according to the invention. In the following, for simplicity, compounds of formula (i) are always referred to, although, optionally, both pure compounds and mixtures with different proportions of isomeric compounds are referred to. Including the meanings (1) to (10) of the CKE group result in the following main structures (1-1) to (1-10):
),
-
where A, B, D, G, Q1, Q2, Q3, Q4, Q5, Q6, W, X, Y and Z have the meaning given above. Including the different meanings (a), (b), (c), (d), (e), (f) and (g) of group G result in the following main structures (Ila) a (Ilg), if CKE is the group (1),
(i-i-g):
where A, B, D, E, L, M, W, X, Y, Z, R1, R2, R3, R4, R5, R6 and R7 have the meanings given above. Including the different meanings (a), (b),
(c), (d), (e), (f) and (g) of group G result in the following main structures (I-2-a) to (I-2-g), if CKE is the group
(2),
(I-2-a): (I-2-b)
(I-2-c): (I-2-d):
(I-2-g):
R °
wherein A, B, E, L, M, W, X, Y, Z, R1, R2, R3, R4, R5, R6 and R7 have the meaning given above. Including the different meanings (a), (b),
(c), (d), (e), (f) and (g) of group G result in the following main structures (I-3-a) to (I-3-g), if the CKE is the group ( 3), (I-3-a): (I-3-b):
(I-3-c): (I-3-d):
(I-3-g)
wherein A, B, E, L, M, W, X, Y, Z, R1, R2, R3, R4, R5, R6 and R7 have the meaning given above. The compounds of formula (1-4) can be presented as a function of the position of substituent G in the two forms
- isomeric of formulas (I-4-A) and (I-4-I)
(I-4-A) (I-4-B) that must be indicated by the dashed line in the formula (1-4). The compounds of formulas (I-4-A) and (I-4-B) can be present both as mixtures and also in the form of their pure isomers. Mixtures of the compounds of formulas (I-4-A) and (I-4-B) can optionally be separated in a known manner by physical methods, for example, by chromatographic methods. For reasons of greater clarity, only one of the possible isomers is indicated below. This does not exclude that the compounds can be presented optionally in the form of isomeric mixtures or in the respective other isomeric form. Including the different meanings (a), (b), (c), (d), (e), (f) and (g) of group G result in the following main structures (I-4-a) a ( I-4-g), if CKE is group (4),
- -
(I-4-g):
where A, D, E, L, M, W, X, Y, Z, R1, R2, R3, R4, R5, R6 and R7 have the meanings given above. Including the different meanings (a), (b),
(c), (d), (e), (f) and (g) of group G result in the following main structures (I-5-a) to (I-5-g), if CKE is the group
(5), (I-5-a): (I-5-b):
(I-5-c): (I-5-d)
(I-5-e): (I-5-f)
(I-5-g):
where A, E, L, M, W, X, Y, Z, R1, R2, R3, R4, R5, R6 and R7 have the meanings given above. The compounds of formula (1-6) can be presented as a function of the position of the substituent G in the two isomeric forms of formulas (I-6-A) and (I-6-B),
(I-6-A) (I-6-B)
what should be indicated by the dashed line in formula (I). The compounds of formulas (I-6-A) and (I-6-B) can be present both as mixtures as well as in the form of their pure isomers. Mixtures of the compounds of formulas (I-6-A) and (I-6-B) can optionally be separated by physical methods, for example, by chromatographic methods. For reasons of greater clarity, only one of the possible isomers is indicated below. This does not exclude that the compounds can be presented optionally in the form of isomeric mixtures or in the respective other isomeric form. Including the different meanings (a), (b), (c), (d), (e), (f) and (g) of group G result in the following main structures (I-6-a) a ( I-6-g):
(I-6-c) (I-6-d):
(I-6-e) (I-6-f):
(I-6-g)
where A, B, Q1, Q2, E, L, M, W, X, Y, Z, R1, R2, R3, R4, R5, R and R7 have the meanings given above. The compounds of formula (1-7) can be presented as a function of the position of the substituent G in the two isomeric forms of formulas (I-7-A) or (I-7-B), which should be indicated by the dashed line in the formula (1-7):
(I-7-A) (I-7-B)
The compounds of formulas (I-7-A) or (I-7-B) can be present both as mixtures as well as in the form of their pure isomers. Mixtures of the compounds of formulas (I-7-A) and (I-7-B) can optionally be separated by physical methods, for example, by chromatographic methods. For reasons of greater clarity, only one of the possible isomers is indicated below. This does not exclude that the compounds can be presented optionally as an isomeric mixture or in the other respective isomeric form.
Including the different meanings (a), (b),
- -
(c), (d), (e), (f) and (g) of group G result in the following main structures (I-7-a) to (I-7-g): (I-7-a) : (I-7-b):
(I-7-c): (I-7-d)
(I-7-e) (I-7-f)
(I-7-g):
where A, B, E, L, M, Q3, Q4, Q5, Q6, W, X, Y, Z, R1, R2, R3, R, R5,
R6 and R7 have the meanings given above. The compounds of formula (1-8) can be presented as a function of the position of the substituent G in the two isomeric forms (I-8-A) and (I-8-B),
what should be indicated by the dashed line in the formula (1-8). The compounds of formulas (I-8-A) and (I-8-B) can be present both as mixtures and also in the form of their pure isomers. Mixtures of the compounds of formulas (I-8-A) and (I-8-B) can optionally be separated in known manner by physical methods, for example, by
- chromatographic procedures. For reasons of greater clarity, only one of the possible isomers is indicated below. This does not exclude that the compounds can be presented optionally in the form of isomeric mixtures or in the respective other isomeric form. Including the different meanings (a), (b), (c), (d), (e), (f) and (g) of group G result in the following main structures (I-8-a) a ( I-8-g), if Het is the group
-
(l-8-g):
where A, D, E, L, M, W, X, Y, Z, R1, R2, R3, R4, R5, R6 and R7 have the meanings given above. The compounds of formula (1-9) can be presented as a function of the position of substituent G in the two isomeric forms of formulas (I-9-A) and (I-9-B), which should be indicated by the dashed line in the formula (1-9).
(I-9-A) (I-9-B)
The compounds of formulas (I-9-A) and (I-9-B) can be present both as mixtures and in the form of their pure isomers. Mixtures of the compounds of formulas (I-9-A) and (I-9-B) can optionally be separated in known manner by physical methods, for example, by chromatographic methods. For reasons of greater clarity, only one of the possible isomers is indicated below. This does not exclude that the compounds can be presented optionally in the form of isomeric mixtures or in the respective other isomeric form. Including the different meanings (a), (b), (c), (d), (e), (f) and (g) of group G result in the following main structures (I-9-a) a ( I-9-g), if CKE is group (9), (I-9-a): (I-9-b):
(I-9-c): (I-9-d):
(I-9-e): (I-9-f):
(I-9-g)
where A, B, D, E, L, M, Q1, Q2, W, X, Y, Z, R1, R2, R3, R, R5, R6 and
R7 have the meanings given above. The compounds of formula (1-10) can be presented in
- function of the position of the substituent G in the two isomeric forms of formulas (I-10-A) and (I-10-B),
(I-10-A) (I-10-B)
what should be indicated by the dashed line in the formula (1-10). The compounds of formulas (I-10-A) and (I-10-B) can be present both as mixtures as well as in the form of their pure isomers. Mixtures of the compounds of formulas (I-10-A) and (I-10-B) can optionally be separated in known manner by physical methods, for example, by chromatographic methods. For reasons of greater clarity, only one of the possible isomers is indicated below. This does not exclude that the compounds can be presented optionally in the form of isomeric mixtures or in the respective other isomeric form. Including the different meanings (a), (b), (c), (d), (e), (f) and (g) of group G result in the following main structures (I-10-a) a ( I-10-g), if CKE is the
.
group (10), (I-10-a): (I-10-b)
(I-10-c) (I-10-d)
(I-10-e): (I-10-f)
(I-10-g)
where A, B, D, E, L, M, Q1, Q2, W, X, Y, Z, R1, R2, R3, R, R5, R and
R7 have the meanings given above. The compounds according to the invention are generally defined by the formula (I). Preferred substituents and / or regions of the radicals indicated in the formulas cited above and hereinafter are exemplified: W is preferably hydrogen, C? -Cg alkyl, alkenyl
C2 ~ Cg, C2-C5 alkynyl, halogen, C? -Cg alkoxy, C-C4 haloalkyl, C-C4 haloalkoxy or cyano, X is preferably halogen, C? -Cg alkyl, C2-Cg alkenyl, C2-Cg alkynyl, C?-Cg alkoxy, C?-Cg-C alco-alkoxy, C-C 4 -haloalkyl, C-C 4 haloalkoxy or cyano, Y is preferably hydrogen, halogen, C-Cg alkyl, C 2 -C 2 alkenyl, C 2 -Cg alkynyl , C?-Cg alkoxy, cyano, C-C4 haloalkyl, haloalkoxy, or is phenyl or pyridyl
- - substituted with V ^ - and V2, vi is preferably halogen, C-C2 alkyl? C alco-Cg alkoxy, C -Chaloalkyl, C -C 4 haloalkoxy, cyano or nitro.
V2 is preferably hydrogen, halogen, C? -Cg alkyl, C-Cg alkoxy or C-C4 haloalkyl, VI and V2 are together preferably C3-C4-alkylene, which may be optionally substituted with halogen and / or C-C2 alkyl and which it may be optionally interrupted with one or two oxygen atoms. Z is preferably hydrogen, halogen, C-Cg alkyl, C-C4 haloalkyl, cyano, C-Cg alkoxy or C-C4 haloalkoxy. CKE is preferably one of the groups
(4),
is preferably hydrogen or C -C 2 alkyl? C al-Cg alkenyl, C alco-C alco-alkoxy, C !!-C alco, Cilt-C alqu alkyl-C-alkyl, optionally substituted each with halogen, C-Cg cycloalkyl optionally substituted with halogen , C-Cg alkyl or alkoxy, in which one or two ring members are optionally replaced not directly adjacent by oxygen and / or sulfur, or is phenyl, naphthyl, hetaryl with 5 to 6 ring atoms (for example furanyl, pyridyl , imidazolyl, triazolyl, pyrazolyl, pyrimidyl, thiazolyl or thienyl), phenyl-C? -Cg alkyl or naphthyl C? -Cg alkyl optionally substituted each with halogen, C? alkyl?
Cg, C?-Cg haloalkyl, C?-Cg alkoxy, C?-Cg haloalkoxy, cyano or nitro, B is preferably hydrogen, C -C 2 alkyl, C alco-Cg alkoxy C alquilo-Cg alkyl or A, B and the carbon atom to which they are attached are the saturated C 3 -C 0 cycloalkyl or unsaturated C 5 -C 0 cycloalkyl, in which a ring member is optionally replaced by oxygen or sulfur and which are optionally substituted once or twice with alkyl C? ~
Cg, C alco-Cg alkoxy C C-Cg alkyl, C3-Cg cycloalkyl C-2 alkoxy, C3-C ciclo cycloalkyl C halo-Cg haloalkyl, C-Cg alkoxy, C alco-Cg alkoxy C -C4 alkoxy , alkylthio C? -Cg, halogen or phenyl or A, B and the carbon atom to which they are attached are C3? C cycloalkyl, which is substituted with an alkylene group optionally substituted with C-C4 alkyl and optionally containing one or two oxygen or sulfur atoms not directly adjacent, or with an alkylenedioxyl group or with an alkylenedithioyl group, which with the carbon atom to which it is attached forms an additional ring of five to eight members or A, B and the carbon atom to which they are joined are C3-C8 cycloalkyl or C5-Cg cycloalkenyl, in which two
- substituents together with the carbon atoms to which they are attached are C2-Cg-alkyndiyl, C2_Cg alkenediyl or C4-Cg-alkanedi-ethiyl each optionally substituted with C? -Cg alkyl, C-Cg alkoxy or halogen, in which optionally substituted a methylene group by oxygen or sulfur, D is preferably hydrogen, C -C 2 alkyl, C 3 -C alkenyl, C 3 -C 8 alkynyl, C 1 -C 6 alkoxy or c 2 -C 8 alkyl optionally each substituted with halogen, C3-C-cycloalkyl optionally substituted with halogen, C-C-alkyl, C-C4-alkoxy or C-C4-haloalkyl, in which a ring member is optionally replaced by oxygen or sulfur or is phenyl, hetaryl with 5 to 6 ring atoms (for example furanyl, imidazolyl, pyridyl, thiazolyl, pyrazolyl, pyrimidyl, pyrrolyl or triazolyl), phenyl-C? -Cg alkyl or hetaryl-C? -Cg alkyl with 5 or 6 ring atoms (for example, furanyl, imidazolyl, pyridyl, thiazolyl, pyrazolyl, pyrimidyl, pyrrolyl, thienyl or triazolyl) each optionally substituted with halogen, C? -Cg alkyl, C-Cg haloalkyl, C? -Cg alkoxy, C? -Cg haloalkoxy, cyano or nitro, or A and D together represent C3-Cg-alkylenei or alquendiil C3 ~ C
each optionally substituted, in which a methylene group is optionally replaced by a carbonyl, oxygen or sulfur group and wherein as substituents are respectively considered: halogen, hydroxy, mercapto or C? -C n alkyl, C?
Cg, alkylthioC? -Cg, C3-C7 cycloalkyl, phenyl or benzyloxy, each optionally substituted with halogen, or a C3-C alkanediyl residue, C3-Cg alkenediyl residue or an additional butadienyl residue, which is optionally substituted with C? -Cg alkyl or wherein optionally two adjacent substituents with the carbon atoms to which they are attached, form an additional saturated or unsaturated ring with 5 or 6 ring atoms (in the case of the compound of formula (1-1 ) A and D are then together with the atoms to which they are attached, for example, the AD-1 to AD-10 groups mentioned below), which may contain oxygen or sulfur, or in which optionally one of the following groups
O R 13 I I X 13: c = N-R N - N \ 14a R
.1 are together C4-C6 alkenidiyl or C3-C6 alkanediyl which are each optionally substituted once or twice with the same or different substituents selected from halogen, hydroxy, C3-C7 cycloalkyl, C1-C6 alkylthio, C1-C6 ay or C1-C10 alkyl, each optionally substituted one to three times with the same or different substituents with halogen, and phenyl or benzyloxy each optionally substituted one to three times with the same or different halogen substituents, C- alkyl Cg or ay C? -Cg y, optionally also containing one of the following
groups
or is crossed by a bridge with a C-C2 alkylene group or with an oxygen atom or
D and X are together preferably C3-Cg-alkynyl optionally substituted one or two times each with the same or different substituents selected from C -C4 alkyl, C-C4 ay
< X is preferably hydrogen, C-Cg alkyl, C-ay
Cg-C -C2 alkyl, C3-Cg cycloalkyl optionally substituted with fluorine, chlorine, C-C4 alkyl, C-C2 haloalkyl or C-C4 ay, in which a methylene group is optionally replaced by oxygen or sulfur, or is phenyl optionally substituted with halogen, C -C alkyl, C -C ay, C -C2 haloalkyl,
- - haloay C -C2, cyano or nitro or
Q2, Q4? Q ^ and Q ^ are independently of each other hydrogen or C -C alkyl,
Q3 is preferably hydrogen, C? -Cg alkyl, C? -Cg ay C -C2 alkyl, alkylthio C? -Cg C -C2 alkyl, C3? C cycloalkyl optionally substituted with alkyl
C-C4 or C-C4-ay, wherein optionally a methylene group is replaced by oxygen or sulfur, or is phenyl optionally substituted with halogen, alkyl C?
C4, C-C4 ay, C-C2 haloalkyl, C-C2 haloay, cyano or nitro. Q1 and Q2 are preferably with the carbon atom to which a C3-C7 ring is optionally substituted with C-Cg alkyl, C-Cg ay or C-C2 haloalkyl, in which a ring member is optionally replaced by oxygen or sulfur, Q3 and Q4 are preferably together with the carbon atom to which a C3-C7 ring is optionally substituted with C1-C alkyl, C-C4 ay or C-C2 haloalkyl, wherein one ring member is optionally replaced by oxygen or sulfur, G is preferably hydrogen (a) or one of the groups
-
OR
R1 (b), A ^ M • # (c), ^ (d). / ^ (e), R6 E (f) or ^ - N ^ Dt (g), especially (a), (b). (c) or (g) L
where E is an equivalent of a metal ion or an ammonium ion,
L is oxygen or sulfur and M is oxygen or sulfur, Rl is preferably C -C20 alkyl, C2-C20 alkenyl C-Cg ay C-Cg alkyl, C-Cg alkyl alkylthio
C? -Cg, poly-ay C -Cg-C? -Cg alkyl each optionally substituted with halogen, or C3-C8 cycloalkyl optionally substituted with halogen, C? -Cg alkyl or C? -Cg ay, in the that optionally one or more (preferably not more than two) not directly adjacent ring members are replaced by oxygen and / or sulfur, phenyl optionally substituted with halogen, cyano, nitro, C? -Cg alkyl, C-Cg ay, haloalkyl C ? ~
Cg, haloalkoxy C? -Cg, alkylthio C? -Cg or alkyl C?
Cg-sulfonyl, phenyl-C? -Cg alkyl optionally substituted with
- halogen, nitro, cyano, C? -Cg alkyl, C? -Cg alkoxy, C-Cg haloalkyl or C? -Cg haloalkoxy, 5- or 6-membered heteroaryl (for example pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl) ) optionally substituted with halogen or C?-Cg alkyl, phenoxy-C-Cg alkyl optionally substituted with halogen or C-Cg alkyl or hetaryloxy-C?-Cg alkyl of 5 or 6 members (eg, pyridyloxy-C alquilo-alkyl) Cg, pyrimidyloxy-C? -Cg alkyl or thiazolyloxy-C? -Cg alkyl optionally substituted with halogen, amino or C? -Cg alkyl,
R 2 is preferably C 2 -C 20 alkenyl C 2 -C 20 alkyl alkyl > alkoxy C? -Cg-alkyl? -Cg, poly-alkoxy C? -Cg-C2-Cg alkyl each optionally substituted with halogen, C3-Cg cycloalkyl optionally substituted with halogen, C? -Cg alkyl or C-alkoxy? -Cg or phenyl or benzyl each optionally substituted with halogen, cyano, nitro, C-Cg alkyl, C? -Cg alkoxy, C? -Cg haloalkyl or C? -Cg haloalkoxy,
R3 is preferably C? -Cg alkyl optionally substituted with halogen or phenyl or benzyl each optionally substituted with halogen, C? -Cg alkyl, C? -Cg alkoxy, haloalkyl
C -C4, haloalkoxy C -C, cyano or nitro,
R4 and R is preferably independently from each other C? -Cg alkyl, C? -Cg alkoxy, C? -Cg-amino alkyl, di- (C? -Cg alkyl) amino, C-Cg alkylthio, alkenylthio ^ 2-Cg , C3-C7 cycloalkylthio each optionally substituted with halogen, or are phenyl, phenoxy or phenylthio each optionally substituted with halogen, nitro, cyano, C-alkoxy
C4, C1-C4 haloalkoxy, C-C4 alkylthio, C-C4 haloalkyl, C-C4 alkyl or C1-C4 haloalkyl,
R ^ and R ^ are independently from each other preferably hydrogen, C-Cg alkyl, C3-Cg cycloalkyl, C-Cg alkoxy, C3-Cg alkenyl, C-Cg alkoxy-C-Cg alkyl each optionally substituted with halogen, phenyl optionally substituted with halogen, haloalkyl C? -Cg, C? -Cg alkyl or C-Cg alkoxy, substituted benzyl
- - optionally with halogen, C? -Cg alkyl, C? -Cg haloalkyl or C? -Cg alkoxy or together are a C3-Cg alkylene radical optionally substituted with C-C4 alkyl, in which a carbon atom is optionally replaced by oxygen or sulfur, R <3> is preferably hydrogen, C [alpha] -Cg alkyl or C-Cg alkoxy each optionally substituted with halogen, C3-Ccycloalkyl optionally substituted with halogen, C-C4 alkyl or C-C-alkoxy, that a methylene group is optionally replaced by oxygen or sulfur, or phenyl, phenyl-C-C4 alkyl or phenyl-C-alkoxy each optionally substituted with halogen, C? -Cg alkyl, C? -Cg alkoxy, haloalkyl C1-C4, haloalkoxy C-C4, nitro or cyano,
R ^ 4a is preferably hydrogen or C? -Cg alkyl or
R ^ 3 and R ^ a are preferably C.sub.2 C-alkynyl,
Rl5a and Rl6a are the same or different and are preferably C -Cg alkyl or Rl5a and Rl6a are preferably a C2-C4 alkanediyl radical, which is optionally substituted
- - with C? -Cg alkyl, C? -Cg haloalkyl or optionally with halogen-substituted phenyl, C? -Cg alkyl, C-C4 haloalkyl, C? -Cg alkoxy, C-C4 haloalkoxy, nitro or cyano, RX ay R ^ a are independently from each other preferably hydrogen, C? -Cg alkyl optionally substituted with halogen or phenyl optionally substituted with halogen, C? -Cg alkyl, alkoxy
C? -Cg, C-C haloalkyl, C-C4 haloalkoxy, nitro or cyano or Rl7a and Rl8a are together with the carbon atom to which they are attached, preferably a C5-C7 carbonyl or cycloalkyl group optionally substituted with halogen, C-alkyl -C4 or C4-C4alkoxy, in which a methylene group is optionally replaced by oxygen or sulfur, R1a and R20a are independently of each other preferably C2-C-C2alkenyl alkyl? C 1 -C 4 alkoxy C 1 -C 4 alkyl or aroino, C 3 -C 0 alkenyl, di- (C 1 -C 4 alkyl) am a no di- (C 3 -C 8 alkenyl) amino. In the definitions of radicals quoted as halogen is fluorine, chlorine, bromine and iodine, especially fluorine,
- - chlorine and bromine. W is particularly preferably hydrogen, fluorine, chlorine, bromine, C -C alkyl, C2-C4 alkenyl, C2-C alkynyl, C-C4 alkoxy, C-C2 haloalkyl or C-C2 haloalkoxy, X is particularly preferably chlorine, bromine, iodine, C-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C-alkoxy, C? -C4 alkoxy-C-C3 alkoxy, C-C2 haloalkyl, C-C2 haloalkoxy or cyano, and is Particular preference in the 4-position is hydrogen, C2-C alkenyl, C2-C4 alkynyl, fluorine, chlorine, bromine, iodine, methoxy, ethoxy, cyano, trifluoromethyl, difluoromethoxy or trifluoromethoxy, Z is particularly preferably hydrogen. W is also particularly preferably hydrogen, fluorine, chlorine, bromine or C-C4 alkyl, X is also particularly preferably chlorine, bromine, C-C4 alkyl, C-C4 alkoxy, C-C2 haloalkyl, C-C2 haloalkoxy or cyano , And it is also with special preference in position 4 the radical
it is also with special preference hydrogen,
- -
V ^ - is also particularly preferably fluorine, chlorine, C-C4 alkyl, C-alkoxy, C-C2 haloalkyl or haloalkoxy C?
C2, cyano or nitro,
V2 is also particularly preferably hydrogen, fluorine, chlorine, C-C4 alkyl, C-C4 alkoxy or C-C2 haloalkyl,
vi and V2 are also particularly preferably together -O-CH2-O- and -O-CF2-O-; W is also particularly preferably hydrogen, fluorine, chlorine, bromine or C-C4 alkyl, X is also particularly preferably chlorine, bromine, C-C4 alkyl, C-C4 alkoxy, C-C2 haloalkyl, C-C2 haloalkoxy or cyano Y is also particularly preferably in the 5-C2-C alkenyl, C2-C4 alkynyl or radical position
Z is also particularly preferably in the 4-position hydrogen, C-C 4 -alkyl chloro, v 1 is also particularly preferably fluorine, chlorine, C-C 4 -alkyl, C-4-alkoxy, C-C 2 haloalkyl or C-2 haloalkoxy , cyano or nitro
V2 is also with particular preference hydrogen, fluorine,
chlorine, C -C alkyl, C-C4 alkoxy or C-C2 haloalkyl,
V ^ - and V2 are also particularly preferably 0-CH-0- and -0-CF -0-; W is also more preferably hydrogen, alkyl C?
C4, C2-C4 alkenyl, C2-C4 alkynyl, C-C4 alkoxy, fluorine, chlorine, bromine or trifluoromethyl, X is especially preferably fluorine, chlorine, bromine, iodine, C-C4 alkyl, C2-C4 alkenyl, alkynyl C2-C4, C -C-alkoxy, C-C4-alkoxy C-C3 alkoxy, haloalkyl C ~
C2, haloalkoxy C -C2 or cyano, Y is also particularly preferably at the 4-C-C4 alkyl position, Z is also particularly preferably hydrogen. w is furthermore particularly preferably hydrogen, fluorine, chlorine, bromine, C-C4-alkyl or C-C4-alkoxy, X is more particularly preferably chlorine, bromine, iodine, C-C-alkyl, C-C4-alkoxy, C-C2 haloalkyl. , haloalkoxy C -C2 or cyano, Y is furthermore particularly preferably in the 4-position hydrogen, chlorine, bromine, iodine, C-C4 alkyl, haloalkyl
C -C2 or haloalkoxy C -C2, Z is also particularly preferably in the 3 or 5 position fluorine, chlorine, bromine, iodine, C -C alkyl, haloalkyl C?
-
C2, C-C4 alkoxy or haloalkoxy C-C2-CKE is particularly preferably one of the groups
A is particularly preferably hydrogen, C? -Cg alkyl, C? -C4 alkoxy C -C2 alkyl each optionally substituted one to three times with fluorine or chlorine,
C 3 -C 6 cycloalkyl optionally substituted one to two times with C -C 2 alkyl or C 2 -C 2 alkoxy (but not in the case of the compounds of formulas (1-3), (1-4),
(1-6) and (1-7)) phenyl or benzyl each optionally substituted once or twice with fluorine, chlorine, bromine, C-C4 alkyl, C-C2 haloalkyl, C-C4 alkoxy, haloalkoxy C -C2, cyano or nitro, B is particularly preferably hydrogen, C-C4-alkyl or C-C2-alkoxy-C-C2-alkyl or A, B and the carbon atom to which they are attached are particularly preferably C3-cycloalkyl. C7 saturated or unsaturated, wherein optionally a ring member is replaced by oxygen or sulfur and which is optionally substituted one to two times with alkyl
C? -Cg, C? -C4 alkoxyC? C2 alkyl, trifluoromethyl, C? -Cg alkoxy, C? -C3 alkoxy C? -C0-cycloalkylmethoxy C3? Alkoxy with the proviso that then
Q3 is especially preferably hydrogen or methyl or
A, B and the carbon atom to which they are attached are especially preferably C5-C-cycloalkyl, which is substituted with an alkylene-diol group optionally substituted with methyl or ethyl optionally containing one or two oxygen or sulfur atoms not
directly adjacent or with an alkylenedioxyl group or with an alkylenedithiol group, which with the carbon atom to which it is attached forms an additional ring of five or six members with the proviso that then Q3 is particularly preferably hydrogen or methyl, or A, B and the carbon atom to which they are attached are particularly preferably C3-Cg cycloalkyl or cycloalkenyl
C5 ~ Cg, in which two substituents together with the carbon atoms to which they are attached are C2-C4-alkyndiyl, C2-C alkenediyl or butadien-diyl each optionally substituted with C-C2alkyl or C-C2alkoxy? with
the condition that then Q3 is particularly preferably hydrogen or methyl, D is particularly preferably hydrogen, C? -Cg alkyl, C3-Cg alkenyl, C4-C4-alkoxy-C2-C3 alkyl, each optionally substituted from a three times with fluorine, it is C3 ~ C cycloalkyl optionally substituted one to two times with C-C4 alkyl, C-C4 alkoxy or C 1 -C 2 haloalkyl in which a methylene group is optionally replaced by oxygen or ( however, not in the case of compounds of formulas (1-1)) is phenyl or pyridyl each optionally substituted one to two times with fluorine, chlorine, bromine,
C -C alkyl, C -C4 haloalkyl, C-C4 alkoxy or C-C4 haloalkoxy, or A and D are especially preferably C3-C5-alkyndiyl optionally substituted one to two times, in which it may be replaced by a group methylene with a carbonyl group (however, not in the case of compounds of formula (1-1)), oxygen or sulfur, suitable substituents being C-C2 alkyl or C-C2-alkoxy or
A and D are (in the case of compounds of formula (1-1)), together with the atoms to which they are attached, one of the groups AD-1 to AD-10:
AD-1 AD-2 AD-3
AD-4 AD-5 AD-6
AD-7 AD-8 AD-9
AD-10
A and p are especially preferably C3-C4-alkynyl optionally substituted one or two times, the same or different with C-C2alkyl or C-C2alkoxy or
D and Q1 are especially preferably C3-C4 alkanediyl, or
X is particularly preferably hydrogen, C -C 4 alkyl, C 1 -C 4 alkoxy C C 2 alkyl, or C 3 C cycloalkyl optionally substituted with methyl or methoxy, wherein a methylene group is optionally replaced by oxygen, Q 2 is preferably hydrogen, methyl or ethyl, Q4, Q5 and Q6 is particularly preferably independently of one another hydrogen or C -C3 alkyl,
Q3 is particularly preferably hydrogen, C-C4 alkyl, or C3-Cg cycloalkyl optionally substituted one to two times with methyl or methoxy, or Q_1 and Q2 are particularly preferably hydrogen, C-C4 alkyl,
C 1 -C 4 alkoxy C -C 2 alkyl, or C 3 -C 6 cycloalkyl optionally substituted with methyl or methoxy, wherein a methylene group is optionally replaced by oxygen, or Q 3 and Q 4 are particularly preferably together with the carbon to which a C5 ~ Cg saturated ring optionally substituted with C-C2 alkyl or C-alkoxy is attached
C2, wherein a ring member is optionally replaced by oxygen or sulfur, with the proviso that then A is particularly preferably hydrogen or methyl, G is particularly preferably hydrogen (a) or one of the groups
where E is an equivalent of a metal ion or an ammonium ion,
L is oxygen or sulfur and M is oxygen or sulfur, R 1 is especially preferably C 1 -Cg alkyl, C 2 -g alkenyl, C 1 -C 4 alkoxy C 2 alkyl, C 1 -C 4 alkyl alkyloxy; the
C -C2 each optionally substituted one to three times with fluorine or chlorine, or C3-C-cycloalkyl optionally substituted one to two times with fluorine, chlorine, C -C2 alkyl or C? -C2 alkoxy, in which optionally one or two ring members not directly adjacent are replaced by oxygen, phenyl optionally substituted one to two times with fluorine, chlorine, bromine, cyano, nitro, C -C4 alkyl, alkoxy
C -C4, haloalkyl C -C2 or haloalkoxy C -C2,
R 2 is particularly preferably C 1 -Cg alkyl, C 2 alkenyl
Cg or C?-C4 alkoxy-C2-C4 alkyl each optionally substituted one to three times with fluorine, C3-Cg cycloalkyl optionally substituted once with C -C2 alkyl or C?-C2 alkoxy or substituted phenyl or benzyl each of them optionally from one to two times with fluorine, chlorine, bromine, cyano, nitro, C-C4 alkyl, C-C3 alkoxy, trifluoromethyl or trifluoromethoxy, R3 is especially preferably C? -Cg alkyl optionally substituted from a three times with fluorine, or phenyl optionally substituted once with fluorine, chlorine, bromine, C -C alkyl, C -C4 alkoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro,
R4 is particularly preferably C? -Cg alkyl, C? -Cg alkoxy,
alkyl C? -Cg-amino, di- (C? -Cg alkyl) amino, alkylthio C?
Cg, C3-C4 alkenylthio, C3 ~ Ccycloalkylthio or is phenyl,
phenoxy or phenylthio substituted optionally once with fluorine, chlorine, bromine, nitro, cyano, C1-C3 alkoxy,
C -C3 haloalkoxy, C-C3 alkylthio, haloalkylthio C?
C3, C -C3 alkyl or trifluoromethyl,
R5 is particularly preferably C alco-Cg alkoxy or Cilt-alkylthio?
Cg,
R ^ is most preferably hydrogen, C-Cg alkyl,
C3-C-cycloalkyl, C-Cg alkoxy, C3-Cg alkenyl, alkoxy
C? -Cg-C -C4 alkyl, phenyl optionally substituted
once with fluorine, chlorine, bromine, fluoromethyl, C-C4 alkyl
or C-C4 alkoxy, or is optionally substituted benzyl
once with fluorine, chlorine, bromine, C-C4 alkyl,
trifluoromethyl or C-C4 alkoxy,
R ^ is particularly preferably C-Cg alkyl, C3-20 Cg alkenyl or C-Cg alkoxy C -C alkyl,
R6 and R 'are especially preferably together a C4-C5 alkylene radical optionally substituted with methyl or
ethyl, in which optionally a group r. methylene by oxygen or sulfur.
In the definitions of radicals mentioned with particular preference halogen is fluorine, chlorine and bromine, especially fluorine and chlorine. W is very particularly preferably hydrogen, methyl, chloro, bromo, ethyl, methoxy, ethoxy or trifluoromethyl, X is very particularly preferably chlorine, bromine, iodine, methyl, ethyl, propyl, methoxy, ethoxy, propoxy, methoxyethoxy, ethoxy- ethoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy or cyano, Y is very particularly preferably in the 4-position hydrogen, chlorine, bromine, iodine, trifluoromethyl or trifluoromethoxy, Z is very particularly preferably hydrogen. W is also very particularly preferably hydrogen, chlorine, bromine, methyl or ethyl, X is also very particularly preferably chlorine, bromine, methyl, ethyl, propyl, methoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy or cyano, and is also very special preference in position 4 the rest
Z is also with very special preference hydrogen, X is also with very special preference fluorine, chlorine,
methyl, methoxy, trifluoromethyl, trifluoromethoxy or cyano,
V2 is also very particularly preferably hydrogen, fluorine, chlorine, methoxy or trilofluoromethyl W is also very particularly preferably hydrogen, chlorine or methyl, X is also very particularly preferably chlorine, methyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy or cyano, And it is also with very special preference in position 5 the rest
Z is also very particularly preferably in the 4-position hydrogen or methyl, vi is also very particularly preferably fluorine, chlorine, methyl, methoxy, trilofluoromethyl, trifluoromethoxy or cyano,
V2 is also very particularly preferably hydrogen, fluorine, chlorine, methyl, methoxy or trifluoromethyl, W is also very particularly preferably hydrogen, methyl, ethyl, methoxy, ethoxy, chlorine or bromine, X is also very particularly preferably chlorine, bromine , iodine, methyl, ethyl, propyl, methoxy, ethoxy, propoxy, methoxy-ethoxy, ethoxy-ethoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy or cyano,
-
And it is also very particularly preferred at the 4-methyl or ethyl position, Z is also very particularly preferably hydrogen, W is also very particularly preferably hydrogen, chlorine, bromine, methyl or ethyl, X is also very particularly preferably chlorine, bromine, iodine, methyl, ethyl, methoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, Y is also very particularly preferably in the 4-position hydrogen, chlorine, bromine, methyl or ethyl, Z is also very particularly preferably in the 3-position or
fluorine, chlorine, bromine, iodine, methyl, ethyl, trifluoromethyl or trifluoromethoxy. CKE is with very special preference one of the groups
A is very particularly preferably hydrogen, C-C4-alkyl or C-C2-alkoxy-C-C2-alkyl substituted each of them optionally from one to three times with fluorine, is cyclopropyl, cyclopentyl or cyclohexyl and only in the case of compounds of formula (1-5) is phenyl optionally substituted one to two times with fluorine, chlorine, bromine, methyl, ethyl, n-propyl, iso-propyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro, it is with very special preference hydrogen, methyl or ethyl
A, and the carbon atom to which they are attached, are very particularly preferably C5-Cg saturated cycloalkyl, wherein optionally one ring member is replaced by oxygen or sulfur and which is optionally substituted once with methyl, ethyl, propyl , isopropyl, methoxymethyl, ethoxymethyl, propoxymethyl, methoxyethyl,
ethoxyethyl, trifluoromethyl, methoxy, ethoxy, propoxy, methoxyethoxy, butoxy, ethoxyethoxy or cyclopropylmethoxy, with the proviso that then Q3 is very particularly preferably hydrogen or A, B and the carbon atom to which they are attached are very particularly preferably cycloalkyl. Cg, which is optionally substituted with alkylenedioxyl group containing two oxygen atoms not directly adjacent, with the proviso that then Q3 is very particularly preferably hydrogen or A, B and the carbon atom to which they are attached are with very special preference C5 ~ Cg cycloalkyl or cycloalkenyl
C5-Cg, in which two substituents together with the carbon atoms to which they are attached are C2-C4-alkyndiyl or C2-C4 alkenediyl or butanediendiyl, with the proviso that
then Q3 is very particularly hydrogen, D is very particularly preferably hydrogen, C-C4 alkyl, C3-C4 alkenyl, C4-C4 alkoxy-C2-C3 alkyl each optionally substituted once or three times with fluorine, cyclopropyl, cyclopentyl or cyclohexyl or (however not in the case of compounds of formula (I-1)) phenyl or pyridyl optionally substituted each
of them once with fluorine, chlorine, methyl, ethyl, n-propyl, iso-propyl, methoxy, ethoxy or trifluoromethyl, or A and D are together very particularly preferably C3-C5-alkyndiyl optionally substituted once with methyl or methoxy, wherein one carbon atom is optionally replaced by oxygen or sulfur or is the group AD-1, or A and Ql are very particularly preferably C3-C4-alkyndiyl optionally substituted once or twice with methyl or methoxy or D and Ql they are very particularly preferably C3-C alkaneyl or
Q1 is very particularly preferably hydrogen, methyl, ethyl, propyl, iso-propyl, cyclopropyl, cyclopentyl or cyclohexyl, Q2 is very particularly preferably hydrogen, methyl or ethyl, Q4, Q-1 and Q ° are with very special preference independently one of another hydrogen or methyl, Q3 is very particularly preferably hydrogen, methyl, ethyl or propyl, or Q3 and Q4 are very particularly preferably together with the carbon to which a saturated C5 ~ Cg ring substituted is attached
optionally once with methyl or methoxy, with the proviso that then A is very particularly preferably hydrogen, G is very particularly preferably hydrogen (a) or one of the groups
-S02-R3 (d) or E (f), in which L is oxygen or sulfur, M is oxygen or sulfur and E is an ammonium ion, R1 is very particularly preferably C? -Cg alkyl, alkenyl
C 2 -C 7, C 1 -C 2 alkoxy C 1 alkyl, C 1 -C 2 alkylthio alkyl
Or each substituted optionally once with chlorine, or cyclopropyl or cyclohexyl each optionally substituted each once with fluorine, chlorine, methyl or methoxy, phenyl optionally substituted once with fluorine, chlorine, bromine, cyano, nitro, methyl , methoxy, trifluoromethyl or trifluoromethoxy, R < it is very particularly preferably C? -Cg alkyl, alkenyl
C2 ~ Cg or C4-C4 alkoxy-C2-C3 alkyl, phenyl or benzyl
each of them optionally substituted once with fluorine, R3 is very particularly preferably C? -Cg alkyl. In particular, the following compounds are to be mentioned in addition to the compounds mentioned in the examples:
Table 1
-
As active ingredients according to the invention, compounds with the radical combinations mentioned in Table 1 for W, X, and Z with the radical combinations mentioned in tables 2a and 2b for A, B and D are particularly preferred. .
Table 2a
-
-
-
Table 2b
As active ingredients according to the invention, compounds with the radical combinations mentioned in Table 1 for W, X, Y and Z with the radical combinations mentioned in Table 3 for A and B are particularly preferred.
Table 3
- -
- -
B
- (CH2) - C- (CH2) 2- CH.OCH,
H - (CH 2,) / 2 X (CH 2) 2- (CH 2) 2 OCH 3
H -CH; X- "(CH,) 3- CH2OCH2CH3
-CH- C- (CH2) 3- (CH2) 2OCH2CH3
- (CH2) - C- (CH2) 2- (CH2) 2OCH2CH3
As active ingredients according to the invention, compounds with the radical combinations mentioned in Table 1 for W, X, Y and Z with the radical combinations mentioned in Table 4 for A and D are particularly preferred.
Table 4
The following compounds are especially highlighted
-
-
- -
spirotetramate I-1-C-2:
I-2-b-l) Spirodiclofen
- -
-2-b-2) Espiromesifeno
-l
-
- -
-
The compounds of formula (I) have a broad insecticidal and / or acaricidal effect, but individually leave something to be desired in terms of effect and / or compatibility with the plants.
The active ingredients can be used in the compositions according to the invention in a wide range of concentration. In this regard, the concentration of the active ingredients in the formulation is usually from 0.1 to 50% by weight. The ammonium and phosphonium salts which, according to the invention, increase the effect of phytosanitary products containing inhibitors of fatty acid biosynthesis, are defined by formula (II)
wherein D is nitrogen or phosphorus, D is preferably nitrogen, R26, R27, R28 and R29 are independently each other hydrogen or Ci-Cg alkyl substituted each of them
optionally or Ci-Cβ alkylene one or more times unsaturated, optionally substituted, wherein the substituents can be selected from halogen, nitro and cyano, R26, R27, R28 and R29 are preferably independently of each other hydrogen or C? -C alkyl each optionally substituted, wherein the substituents may be selected from halogen, nitro and cyano, R26, R27, R28 and R29 are particularly preferably independently of one another hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl or tere-butyl, R26, R27, R28 and R29 are very particularly preferably hydrogen,
R26, R27, R28 and R29 are also very preferably simultaneously methyl or simultaneously ethyl, n is 1, 2, 3 or 4, n is preferably 1 or 2, R30 is an inorganic or organic anion, R30 is preferably hydrogen carbonate, tetraborate , fluoride, bromide, iodide, chloride, monohydrogen phosphate, dihydrogen phosphate, hydrogen sulfate, tartrate, sulfate, nitrate, thiosulfate, thiocyanate, formate, lactate, acetate, propionate, butyrate, pentanoate, citrate or oxalate, R30 is also preferably carbonate, pentoborate,
sulfite, benzoate, hydrogen oxalate, hydrogen citrate, methylsulfate or tetrafluoroborate, R 30 is especially preferably lactate, sulfate, nitrate, thiosulfate, thiocyanate, citrate, oxalate acetate or formate, R 30 is also particularly preferably monohydrogen phosphate or dihydrogen phosphate and R 30 is very particularly preferred thiocyanate, dihydrogen phosphate, monihydrogen phosphate or sulfate. The ammonium and phosphonium salts of formula (II) can be used over a wide range of concentration for the increase of the effect of phytosanitary products containing ketoenols. In general, the ammonium or phosphonium salts are used in phytosanitary products ready for use in a concentration of 0.5 to 80 mmol / l, preferably of 0.75 to 37.5 mmol / l, especially preferably 1.5 at 25 mmol / l. In the case of the formulated product, the concentration of ammonium and / or phosphonium salt in the formulation is selected so that it is found after dilution of the formulation in the concentration of active principle desired in these given, preferred or especially preferred general ranges. The concentration of the salt in the formulation is usually 1 to 50% by weight in this respect. In a preferred embodiment of the invention is added to plant protection products for the increase of the
- effect not only an ammonium and / or phosphonium salt, but also a penetration facilitator. It is pointed out as completely surprising that an even more profound increase in effect is observed in these cases. The present invention therefore also provides the use of a combination of penetration facilitators and salts of ammonium and / or phosphonium for the increase of the effect of phytosanitary products, containing cyclic ketoenols substituted with phenyl insecticide effect as active ingredient. The invention also provides agents containing phenyl substituted cyclic ketoenols of insecticidal effect, penetration facilitators and salts of ammonium and / or phosphonium, specifically including both active ingredients formulated as well as ready-to-use products (spray liquors). Finally, the invention further provides the use of these agents for the control of parasitic insects. As penetration facilitators are considered in relation to the present all those substances that are normally used to improve the penetration of agrochemical active ingredients in plants. In this regard, penetration facilitators are defined because they penetrate from the aqueous spray liquors and / or from the spray layer into the cuticle of the plants and thereby increase the mobility of the active ingredients in the cuticle. It can
- - use the procedure described in the literature (Baur et al., 1997, Pes ti cide Science 51, 131 to 152) for the determination of this property. As penetration facilitators, for example, alkanol alkoxylates are taken into account. According to the invention, penetration facilitators are alkanoyl alkoxylates of the formula RO- (-OA) VR '(III) in which R is straight or branched chain alkyl with 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, OA is a residue of ethylene oxide, a residue of propylene oxide, a remainder of butylene oxide, or mixtures of ethylene oxide and propylene oxide moieties or butylene oxide moieties and v is a number from 2 to 30. A preferred group of penetration facilitators are alkanol alkoxylates of the formula RO- (-OE-) ) nR '(Ill-a) in which R has the meaning given above, R' has the meaning given above,
OE is -CH2-CH2-0- and n is a number from 2 to 20. A further preferred group of penetration facilitators are alkanol alkoxylates of the formula RO- (-EO-) p- (-PO-) gR '(III -b)
where R has the meaning given above, R 'has the meaning given above, OE is -CH2-CH2-0-, CH-CH-0 CH, PO is 3, p is a number from 1 to 10 and q is a number from 1 to 10. A further preferred group of penetration facilitators are alkanol alkoxylates of the formula RO- (-OP-) r- (OE-) SR '(III-c)
wherein R has the meaning given above, R 'has the meaning given above, OE is -CH2-CH2-0-, -CH-CH-0 CH, OP is' 3
r is a number from 1 to 10 and s is a number from 1 to 10.
-
A further preferred group of penetration facilitators are alkanol alkoxylates of the formula RO- (-EO-) p- (-BO-) qR '(Ill-d) in which R and R' have the meanings given above, OE is CH2-CH2-0-, -CH-CH2-CH-0 CH, OB is 3, p is a number from 1 to 10 and q is a number from 1 to 10. A further preferred group of penetration facilitators are alkanol alkoxylates of formula RO- (-OB-) r- (-OE-) SR '(Ill-e) in which R and R' have the meanings given above,
OE is CH2-CH2-0-, r is a number from 1 to 10 and s is a number from 1 to 10. A further preferred group of penetration facilitators are alkanol alkoxylates of the formula CH3- (CH2) t-CH2-0 - (-CH -CH2-0-) uR '(Ill-f) in which
R 'has the meaning given above, t is a number from 8 to 13 or is a number from 6 to 17. In the formulas given previously are R is preferably butyl, i-butyl, n-pentyl, i-pentyl, neopentyl, n-hexyl, i-hexyl, n-octyl, i-octyl, 2-ethyl-hexyl, nonyl, nonyl, decyl, n-dodecyl, i-dodecyl, lauryl, myristyl, i-tridecyl, trimethyl-nonyl, palmityl, stearyl or eicosyl. As an example for an alkanol alkoxylate of formula (III-c) there is mentioned 2-ethylhexyl alkoxylate of formula CH: -CH; -CH; -CH; -CH- -CH; - (PO) - (EO) 6-H III-c- C2H5
where OE is -CH2-CH2-0-, CH-CH-O-CH, OP is and the numbers 8 and 6 are average values. As an example of an alkanol alkoxylate of formula (III-d), the formula CH3- (CH2) IQ-O- (-OE-) 6- (-OB-) 2-CH3 (Ill-d-) is mentioned.
-
where OE is CH2-CH2-0-, -CH2-CH CH-0 CH, OB is and the numbers 10, 6 and 2 are average values. Especially preferred alkanol alkoxylates of formula (Ill-f) are compounds of this formula, wherein t is a number from 9 to 2 and u is a number from 7 to 9. Alkaloy alkoxylate of formula is to be mentioned with particular preference (III-f-1) CH3- (CH2) t-CH2-0- (-CH2-CH2-0-) uH (III-f-1) where t is the average value 10.5 yu is the value average 8.4. The alkanol alkoxylates are generally defined by the above formulas. These substances are mixtures of substances of the given type with different chain lengths. For the Indexes, mean values are calculated which can also fluctuate in whole numbers. The alkanyl alkoxylates of given formulas are known and can be obtained commercially in part or
they can be prepared according to known processes (see WO 98-35 553, WO 00-35 278 and EP-A 0 681 865). Penetration facilitators also take into account, for example, substances which promote the solubility of the compounds of formula (I) in the spray layer. To these belong, for example, mineral or vegetable oils. As oils are considered all the optionally modified mineral or vegetable oils that can be normally used in agrochemicals. Mention may be made, by way of example, of sunflower oil, rapeseed oil, olive oil, castor oil, rapeseed oil, corn seed oil, cottonseed oil and soy bean oil or the esters of the oils. mentioned. Rapeseed oil, sunflower oil and its methyl or ethyl esters are preferred. The concentration in penetration facilitator can be varied in the agents according to the invention over a wide range. In a formulated phytosanitary product, it is generally from 1 to 95% by weight, preferably from 1 to 55% by weight, particularly preferably from 15 to 40% by weight. In the ready-to-use products (spray liquors) the concentration is generally between 0.1 and 10 g / 1, preferably between 0.5 and 5 g / 1. Indicable combinations according to the invention of active principle are indicated in the following table,
salt and penetration facilitator. In this respect "according to assay" means that each compound is suitable when in the cuticle penetration test (Baur et al., 1997, Pes ti cide Science 51, 131 to 152) acts as a penetration facilitator.
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No. Principle Salt Active penetration facilitator 75 (Ila-3) Ammonium sulfate According to test 76 (Ila-3) Ammonium lactate According to test 77 (Ila-3) Ammonium nitrate According to test 78 (Ila-3) Thiosulfate According to Ammonium test 79 (Ila-3) Thiocyanate from According to test ammonium 80 (Ila-3) Ammonium citrate According to test 81 (Ila-3) Ammonium oxalate According to test 82 (Ila-3) Ammonium formate According to test 83 (Ila-3) 3) Hydrogen phosphate According to test ammonium 84 (Ila-3) Dihydrogen phosphate According to test of ammonium 85 (Ila-3) Ammonium carbonate According to test 86 (Ila-3) Ammonium benzoate According to test 87 (Ila-3) Ammonium sulphite test 88 (Ila-3) Ammonium benzoate According to test 89 (Ila-3) Hydrogenoxalate of According to test ammonium 90 (Ila-3) Hydrogenocitrate of According to ammonium test
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No. Principle Salt Active penetration facilitator 330 (I-l-a-9) Oxalate of According to tetraethylammonium assay 331 (I-l-a-9) Formate of According to test tetraethylammonium 332 (Ila-9) Hydrogen phosphate of According to test tetraethylammonium 333 (Ila-9) Dihydrogen phosphate According to test of tetraethylammonium 334 (Ila-10) Ammonium sulfate According to test 335 (Ila-10) Ammonium lactate According to test 336 ( Ila-10) Ammonium nitrate According to test 337 (Ila-10) Thiosulfate of According to test ammonium 338 (Ila-10) Thiocyanate of According to ammonium test 339 (Ila-10) Ammonium citrate According to test 340 (Ila-10) Oxalate of ammonium According to test 341 (Ila-10) Ammonium formate According to test 342 (Ila-10) Hydrogen phosphate According to ammonium test 343 (Ila-10) Dihydrogen phosphate According to ammonium test
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No. Principle Salt Active penetration facilitator 357 (Ila-10) Oxalate of According to tetramethyl ammonium test 358 (Ila-10) Formate of According to tetramethylammonium test 359 (Ila-10) Hydrogen phosphate of According to tetramethylammonium test 360 (Ila-10) Dihydrogen phosphate According to test of tetramethylammonium 361 (Ila-10) Sulphate of According to tetraethylammonium test 362 (Ila-10) Lactate of According to tetraethylammonium test 363 (Ila-10) Nitrate of According to tetraethylammonium test 364 (Ila-10) Thiosulfate of According to tetraethylammonium test 365 (Ila-10) 10) Thiocyanate of According to tetraethylammonium test 366 (Ila-10) Citrate of According to tetraethylammonium test 367 (Ila-10) Oxalate of According to tetraethylammonium test
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No. Principle Salt Active penetration facilitator 597 (Ila-17) Thiocyanate of According to ammonium test 598 (Ila-17) Ammonium citrate According to test 599 (Ila-17) Ammonium oxalate According to test 600 (Ila-17) Ammonium formate According to test 601 (Ila-17) Hydrogen phosphate of According to test ammonium 602 (Ila-17) Dihydrogen phosphate According to ammonium test 603 (Ila-17) Ammonium carbonate According to test 604 (Ila-17) Ammonium benzoate According to test 605 (Ila-17) 17) Ammonium sulphite According to test 606 (Ila-17) Ammonium benzoate According to test 607 (Ila-17) Hydrogenoxalate of According to ammonium test 608 (Ila-17) Hydrogenocitrate of According to ammonium test 609 (Ila-17) Ammonium acetate According to Test 610 (Ila-17) Sulphate of According to tetramethylammonium test 611 (Ila-17) Lactate of According to tetramethylammonium test
No. Principle Salt Active penetration facilitator 612 (Ila-17) Nitrate of According to tetramethylammonium test 613 (Ila-17) Thiosulfide of According to tetramethylammonium test 614 (Ila-17) Thiocyanate of According to tetramethylammonium test 615 (Ila-17) Citrate of According to tetramethylammonium test 616 (Ila-17) Oxalate of According to tetramethylammonium test 617 (Ila-17) Formate of According to tetramethylammonium test 618 (Ila-17) Hydrogen phosphate of According to tetramethylammonium test 619 (Ila-17) Dihydrogenphosphate According to tetramethylammonium 620 test (Ila -17) Sulphate of According to tetraethylammonium test 621 (Ila-17) Lactate of According to tetraethylammonium test 622 (Ila-17) Nitrate of According to tetraethylammonium test
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No. Principle Salt Acting developer of penetration 802 (1-2-3-2) Formate of According to tetrsmethylsmonium test 803 (1-2-3-2) Hydrogenphosphate of According to tetrsmethylsmonium test 804 (1-2-3-2) Dihydrogenphosphine According to Tetramethylsmonium test 805 (1-2-3-2) Sulphate of According to tetraethylammonium test 806 (1-2-3-2) Lactate of According to tetraethylammonium test 807 (1-2-3-2) Nitrate of According to test tetrsetilsmonio 808 ( 1-2-3-2) Thiosulfate of According to tetraethylsmonium test 809 (1-2-3-2) Thiocyst of According to test tetrsetilsmonio 810 (1-2-3-2) Citrsto of According to tetrsetilsmonio 811 test (1-2-3 -2) Oxslsto of According to tetrsetilsmonium test 812 (1-2-3-2) Formisto de Enssyo tetrsetilsmonio
No. Principle Salt Active penetration facilitator 813 (I-2-a-2) Hydrogen phosphate According to tetraethylammonium test 814 (I-2-a-2) Dihydrogenphosphate According to tetrsetilamonium test 815 (1-2-3-3) Sulphate of Ammonium According to Test 816 (1-2-3-3) Ammonium Lactate According to Test 817 (1-2-3-3) Ammonium Nitrate According to Test 818 (1-2-3-3) Thiosulfate According to Ammonium Test 819 ( 1-2-3-3) Thiocyanate Based on Ammonium test 820 (1-2-3-3) Ammonium citrate According to Test 821 (1-2-3-3) Ammonium Oxallate According to Test 822 (1-2-3 -3) Ammonium formate According to test 823 (1-2-3-3) Hydrogen phosphate According to test ammonium 824 (1-2-3-3) Dihydrogen phosphate According to ammonium test 825 (1-2-3-3) Carbonsto ammonium According to test 826 (1-2-3-3) Ammonium benzoate According to test 827 (1-2-3-3) Ammonium sulphite According to test 828 (1-2-3-3) Ammonium benzoate According to test
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N ° Principle Salt Active absorbing dispersant 840 (1-2-3-3) Hydrogen phosphate based on tetramethylammonium assay 841 (1-2-3-3) Dihydrogen phosphate According to tetramethyl ammonium test 842 (1-2-3-3) Sulphate According to tetraethylammonium test 843 (I-2-a-3) Lactsto of According to tetrsetilsmonio test 844 (1-2-3-3) Nitrate of According to test tetrsetilsmonio 845 (1-2-3-3) Thiosulfate of According to test tetraetilsmonio 846 ( 1-2-3-3) Thiocycline of According to tetraethylammonium test 847 (1-2-3-3) Citrate of According to tetraethylammonium test 848 (1-2-3-3) Oxallate of According to tetrsetilsmonium test 849 (1-2-3 -3) Formisto de According to tetrsetilsmonio 850 assay (1-2-3-3) Hydrogenofosfsto of According to tetrsetilsmonio test
N ° Principle Ssl Penetrator penetration facility 851 (1-2-3-3) Dihydrogenphosphate According to tetrsetilsmonium test 852 (1-2-3-4) Ammonium sulfate According to test 853 (1-2-3-4) ammonium According to test 854 (1-2-3-4) Ammonium nitrate According to test 855 (1-2-3-4) Thiosulfate of According to ammonium test 856 (1-2-3-4) Thiocyanide of According to ammonium test 857 ( 1-2-3-4) Ammonium Citrate According to Test 858 (1-2-3-4) Ammonium Oxallate According to Test 859 (1-2-3-4) Ammonium Formate According to Test 860 (1-2-3) -4) Hydrogen phosphate According to the ammonium test 861 (1-2-3-4) Dihydrogen phosphate According to the ammonium test 862 (1-2-3-4) Ammonium carbonate According to test 863 (1-2-3-4) Benzoate ammonium According to test 864 (1-2-3-4) Ammonium sulphite According to test 865 (1-2-3-4) Ammonium benzoate According to test 866 (I-2-a-4) Hydrogenoxalate of According to ammonium test
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N ° Principle Ssl Active penetration fixator 867 (1-2-3-4) Hydrogen according to 3month test 868 (1-2-3-4) Ammonium acetate According to test 869 (1-2-3-4) Sulphate of According to tetrsmethylsmonium test 870 (1-2-3-4) Lsctsto of According to tetramethyl ammonium test 871 (1-2-3-4) Nitrate of According to tetrsmethylammonium test 872 (1-2-3-4) Thiosulfate of According to tetramethyl ammonium test 873 ( 1-2-3-4) Thiocyanide of According to tetrsmethylsmonium assay 874 (1-2-3-4) Citrate of According to tetramethyl ammonium assay 875 (1-2-3-4) Oxslsto of According to tetrsmethylsmonium assay 876 (1-2-3 -4) Formisto de According to Tetrsmethylsmonium assay 877 (1-2-3-4) Hydrogenofosfsto of According to Tetrsmethylsmonium assay
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N ° Principle Ssl Fscilitator of active penetration 966 (1-4-3-1) Thiosulphate of According to enssyo ammonium 967 (1-4-sl) Thiocyanate of According to enssyo ammonium 968 (1-4-3-1) Ammonium citrate According to enssyo 969 (1-4-3-1) Ammonium oxallate According to enssyo 970 (1-4-3-1) Ammonium formate According to enssyo 971 (1-4-3-1) Hydrogen phosphate according to enssyo ammonium 972 (1- 4-3-1) Dihydrogen phosphate According to ammonium test 973 (1-4-3-1) Ammonium carbonate According to test 974 (1-4-3-1) Ammonium benzoate According to test 975 (1-4-3-1) ) Ammonium sulphite According to test 976 (1-4-3-1) Ammonium benzoate According to enssyo 977 (1-4-3-1) Hydrogenoxalate of According to enssyo ammonium 978 (1-4-3-1) Hydrogenocitrate of According to enssyo ammonium 979 (I-4-sl) Ammonium acetate According to enssyo 980 (I-4-sl) Sulphate of According to enssyo tetramethilmonium
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N ° Principle Ssl Penetration active facilitator 1220 (I-8-sl) Hydrogenphosphate According to tetrsetilsmonium test 1221 (I-8-sl) Dihydrogenphosphate According to tetryphthalammonium 1222 (I-8-S-2) Smonium sulphate According to enssyo 1223 (1-8-3-2) Smonium Lysis According to Ensyyo 1224 (1-8-3-2) Nummary of Smonium According to Enssy 1225 (1-8-3-2) Thiosulfase of According to Enssyo Smonius 1226 (1-8- 3-2) Thiocyanate of According to enssyo smonium 1227 (1-8-3-2) Citrate of smonium According to enssyo 1228 (1-8-3-2) Ammonium oxalate According to enssyo 1229 (1-8-3-2) Formate ammonium According to test 1230 (1-8-3-2) Hydrogen phosphate According to test smonium 1231 (1-8-3-2) Dihidrogenofosfsto According to ammonium test 1232 (1-8-3-2) Csrbonsto de smonio According to enssyo 1233 (1-8-3-2) Ammonium benzoate According to enssyo 1234 (1-8-3-2) Smonium sulphite According to enssyo 1235 (1-8-3-2) Ammonium benzoate According to enssyo
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The phytosanitary products according to the invention can also contain other components, for example, surfactants and / or dispersion aids or emulsifiers.
As non-ionic surfactants or dispersion aids all substances of this type are taken into account
type that can be used normally in agrochemical agents. Preference is given to block copolymers of poly (ethylene oxide) -poly (propylene oxide), polyethylene glycol ethers of linear alcohols, reaction products of fatty acids with ethylene oxide and / or propylene oxide, in addition to poly (vinyl alcohol). ), polyvinylpyrrolidone, or poly (vinyl alcohol) and polyvinylpyrrolidone polymers, such as (meth) scrilic acid copolymectives and (meth) -silic acid esters, as well as slical ethoxylates and slurry ethoxylates, which can optionally be phosphinated and optionally neutralized with bases, where mention is made, by way of example, of ethoxylates of sorbitol, ssi as polyoxyalkyleneamine derivatives. As ammonium surfactants, all substances of this type that can normally be used in agrochemical compositions are normally considered. Alkali metal and alkaline earth metal ssles of sulkylsulfuric acids or slical sulfur acids are preferred. Another preferred group of ammonium surfactants or dispersing aids are poorly soluble in vegetable solids of poly (styrene-sulphonic acids), poly (vinylsulfuric acid) ssels, condensation products of naphthalenesulfonic acid-formsldehyde, salts of acid condensation products naphthalenesulfonic, acid
phenolsulfonic and formsldehyde ssi as ssles of lignin sulphonic acid. They are specific substances, which may be contained in the formulations according to the invention, emulsifiers, antiperspirants, preservatives, antioxidants, dyes and materisols of inert csrg3. Preferred emulsifiers are ethoxylated nonylphenols, reaction products of alkylphenols with ethylene oxide and / or propylene oxide, arylalkylphenols ethoxylated, in addition to ethoxylated and propoxylated arylalkyphenols, such as srylethylethoxylates or silyl-letoxypropoxysulfonates and phosphines, where they are mentioned by way of example sorbitan derivatives, such as poly (ethylene oxide) - sorbitan esters and fatty acid and sorbitan esters and fatty acid. The following examples serve to clarify the invention and should not be interpreted in any way as limiting. Example Al: Increased penetration into the plant by ammonium or phosphonium salts and synergistic increase of penetration into the plant by ammonium / phosphonium salts in combination with penetration facilitators In this test the penetration of active principles was measured 3 days of cuticul sislsdss enzymatically from apple tree hojss. Leaves that were cut in the full development stage of the Golden Delicious apple tree were used. The isolation
of the cuticles was performed so that in the first lugsr discs of leaflets marked by the lower part with dye and covered by stamping were filled in with a vacuum infiltration with a pectin solution (0.2 to 2%). pH between 3 and 4, then sodium azide was added and the leaf discs treated were left to rest until the destruction of the original foliar structure and until the detachment of the non-cellular cuticulss. Then only the open cuticles and filaments of the upper parts of the leaves were used. These were repeatedly washed several times with water and a pH7 solution of pH value 7. The clean cuticles obtained were spread finely on Teflon plscss and smoothed and dried with a gentle sire current. In the next etsps, the cuticle membranes 3 were inserted if obtained by membrane transport studies in diffusion cells (= charsers of trsnsporte) of stainless steel. To do this, the cuticles were placed with a pinz centered on the edges coated with silicone grease from the diffusion cells and closed with an equally greased ring. The disposition was selected so that the outer morphological part of the cuticles were directed by hscis fuers, by tsnto hscis el sire, mientrss that part
interior originsl dsbs hscis the interior of the diffusion cell. The diffusion cells were filled with a solution of ethylene glycol / agus si 30%. In order to determine the penetration, 10 μl of the pulverization rate of the following composition was applied respectively to the outer part of the cuticles. The addition of the spray broth was carried out with local hardness agar medium. After the spraying of the sprays, the water was allowed to evaporate, the chambers were placed in thermoset piles, where the temperature and humidity could be adjusted in the cuticle by a gentle air current on the cuticle with the spray layer (20 ° C, 60% relative humidity). At regular intervals they were collected with an automatic sampler aliquots and the content was determined in principle active with HPLC. The results of the test are shown in the following table. In terms of the easy data, the average values are from 8 to 10 measurements. It is clearly seen that ammonium sulfate alone clearly improves penetration and together with RME ds an oversimilar effect (synergistic).
Table A-1
RME = methyl ester of colza sceite (use as formulated as 500 EW, concentration deficit in g of active principle /
1) AS = ammonium sulfate EC = concentrated emulsionsble
Example A-2 It took 3 csbo the example A-2 of forms snálogs if example A-l.
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Table A-2
RME = Rapeseed oil methyl ester (use formulated as 500 EW, concentration data in g of active ingredient /
1) AT = Ammonium thiocyanide EC = Emulsifiable concentrate Emulsifier W = Emulsifier
Example A-3 We took 3 csbo the example A-3 of forms snálogs if example A-l.
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Table A-3
RME = methyl ester of colza oil (use formulated as 500 EW, concentrate concentration in g of active principle /
1) EC = emulsifiable emulsifier concentrate W = emulsifier Example B: increase of the effect by ammonium / phosphonium salts The following tests confirm that the ammonium or phosphonium salts can further strengthen the effect of phytosanitary products containing ketoenol.
Test with Myzus persicae Solvent: 7 pst by weight of dimethylformsmids Emulsifier: 1 pst by weight of slickrils polypollycol ether Psrs the preparation of an appropriate active principle preparation is mixed 1 pst in weight of active principle with the amounts dsdss of solvent and emulsifier and diluted the concentrate with water hssts the concentration desesds. Where necessary additions of smonium ssels, phosphonium ssles or penetration facilitators, the corresponding quantity is pipetted after the respective dilution of the prepared ready solution. They are trstsn plsntss of pepper unifolisdss (Capsi cum annuum), which are infestsdss strongly with the green aphid of the peach tree (Myzus persi caei), medisnte pulverizsción of the upper part of the leaves (volume of spray 600 l / ha) with the preparation of working principle s concentration desesds. After the desesdo time you determine the extermination in%. In this respect 100% significs that all animsles were exterminated; 0% significs that snimsl slguno was not exterminated.
Table B
AS = Smonium sulphite
Example C: increase of the effect by ammonium / phosphonium salts in combination with penetration facilitators The following data confirm that 13S smonium or phosphonium ssols can further strengthen the effect, also in the 3plication of compositions fitossnitsriss listss psrs use, containing the penetration testers psrs the increase of the effect. Test with Myzus persicae Solvent: 7 psrtes by weight of dimethylformamide Emulsifier: 1 part by weight of alkylsrilpolyglycol ether Psrs ls prepsession of an active ingredient preparation
Spropisds mix 1 psu in weight of active principle with the solvent and emulsifier amounts and dilute the concentration with sgus hasts ls concentration desesds. Where do you need adicionsr ssles smonium, phosphonium ssles or penetration fscilitsdores pipettes ls csntidsd corresponding trss ls dilution respective of the solution of preparsdo list. They are treated plsntss of pepper unifolisdss (Capsicum annuum), which are infestsdss strongly with the green aphid of the peach tree (Myzus persicaei), medisnte pulverizsción of ls psrte superior of the leaves (volume of pulverización 600 l / has) with the prepsrsción of principle sctivo 3 ls concentration desesds. After the desesdo time you determine the extermination in%. In this respect 100% significs that all the snimales were exterminated; 0% significs that snimsl slguno was not exterminated. Table C
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RME = Colic sceite methyl ester (use formulated as 500 EW, concentrate concentration in g of active principle / 1) AS = Ammonium sulfate Example D: increase in effect by ammonium / phosphonium salts Assay with Myzus persicae Solvent: 7 parts by weight of dimethylformamide
Emulsifier: 2 psches by weight of slquilsrilpolyglycolether Psrs ls prepsession of a preparation of active principle. Approx. 1 psu in weight of active principle is mixed with the amounts of solvent and emulsifier and the concentrate is diluted with agus hssts ls concentration desesds. Psr3 the use with smonium or phosphonium ssels are incorporated at a concentration of 1000 ppm of the spray liquor. There are several pepper plsntss (Capsi cum annuum), which are strongly infested with the green peach aphid (Myzus persi caei), which is pulverized with empspsed at the desesds concentration. After the desesdo time you determine the extermination in%. In this respect 100% significs that all animsles were exterminated; 0% significs that snimsl slguno was not exterminated.
Table D
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AS = Ammonium sulphate Example E Test with Aphis gossypii Solvent: 7 pbs by weight of dimethylformamide Emulsifier: 2 parts by weight of alkylaryl polyglycol ether Psrs ls prepsession of a prepsession of active principle 3propi3d3 is mixed 1 psu by weight of active principle with the given quantities of solvent and emulsifier and dilute the concentrate with sgus containing emulsifier to the desired concentration. For use with ammonium or phosphonium ssels, these are incorporated at a concentration of 1000 ppm of the spray mixture. They are treated with cottonseed (Gossypi um hirsutum), which are heavily infested with cotton aphid (Aphis gossypn), by spraying with empspsdo with preliminary active principle prepsession 3 ls concentration desesds. After the desesdo time the extermination in% is determined. In this respect 100% means that all the aphids were exterminated; 0% means that no aphid was killed.
- Table E
Smonium sulphite
Example F: Increase of the effect by ammonium / phosphonium salts in combination with penetration facilitators Test with Myzus persicae Solvent: 7 pbs by weight of dimethylformsmids Emulsifier: 2 pbs by weight of slickyl polyglycol ether PSrs preparation of a prepsession of active principle apropisds shall be mixed 1 psu in weight of active principle with the given amounts of solvent and emulsifier and the concentrate is diluted with agus hssts ls concentration desesds. For the use with smonium or phosphonium ssles and penetration promoter (methyl ester of colza oil 500 EW) these are incorporated respectively at a concentration of 1000 ppm of the pulverization rate. There are many pepper plsntss (Capsi cum annuum), which are strongly infested with the green peach aphid (Myzus persicaei), with pulverization with empspsdo with prepsurance of active principle at the desesds concentration. After the desired time the extermination is determined in%. In this respect 100% means that all the animies were exterminated; 0% means that animsl slguno was not exterminated.
- Table F
500 EW, concentration point in g of active principle / 1)
AS = Smonium sulphide Example G Test with Aphis gossypii Solvent: 7 parts by weight of dimethylformamide
Emulsifier: 2 parts by weight of alkylsrilpolyglycol ether Psrs ls prepsurance of a prepsession of active principle is mixed 1 psu in weight of active principle with the solvent and emulsifier dsdsss concentrations and the concentration is diluted with sgus containing emulsifier hssts the desesds concentration. Psrs use with ssl or ssl
Phosphonium and penetration promoter (methyl ester of colza oil 500 EW) are incorporated respectively at a concentration of 1000 ppm of the pulverization rate. There are many plsntss of cotton (Gossypi um hirsutum), which are heavily infested with cotton slime. { Aphis gossypii), medium spray with empspsdo with ls prepsrsion of active principle at the desired concentration. After the desired time the extermination is determined in%. In this respect 100% means that all the aphids were exterminated, 0% means that no aphids were exterminated. Table G
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RME = methyl ester of colza oil (formulated as 500 EW, concentration deficit in g of active principle / 1)
AS = Smonium Sulfide It should be noted that with reference to this date, the best method known by the applicant to carry out the invention cited, is the results of the present description of the invention.
Claims (3)
- I-2-b-l) Spirodiclofen I-
- 2-b-2) Espiromesif eno
- 3-2; - 6. Composition in accordance with cuslquiers of lss claims 1 s 5, characterized in that the content of active principle is between 0.5 and 50% by weight. - 7. Composition of conforids with co-drivers of claims 1 to 6, characteres because the ssl content of smonium or phosphonium is between 0.5 and 80 mmol / l. 8. Composition of compliant with cuslquiers of claims 1 to 7, charac- terized because D is nitrogen. 9. Composition according to claim 8, characterized in that R30 is hydrogen carbonate, tetraborate, fluoride, bromide, iodide, chloride, monohydrogen phosphate, dihydrogenphosphate, hydrogen sulfate, tartrate, sulfate, nitrate, thiosulfide, thiocyst, formate, lactate, acetose, propionate, butyrate, pentsnoste, citrsto or oxalate. 10. Composition according to claim 8, csrscterizsds because R30 is carbonate, pentaborate, sulfite, benzoate, hydrogen peroxide, hydrogencarbonate, methylsulfate or tetrafluoroborate. 11. Composition of conformity with claim 8, characterized in that R30 is lactate, sulfate, nitrate, thiosulfsto, thiocisnsto, citrsto, oxalate or formate. 12. Composition according to claim 8, characterized in that R30 is thiocisst, dihydrogenphosphate, monohydrogenphosphate or sulfide. 13. Composition of conformity with cuslquiers of claims 1 3 12, characterized in that it contains at least one penetration facilitator. - - 14. Composition of confordsd with ls reivindicsción 13, csrscterizsds because the penetration fscilitsdor is a slcoxilsto of slcohol fatty of formula (III) RO - (- OA) VR '(III) in ls that R is slquilo of straight chain or ramificsds with 4 3 20 carbon atoms, R 'is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl or n-hexyl, OA is a rsdicsl of ethylene oxide, a rsdicsl of propylene oxide, a rsdicsl of butylene oxide or mixtures of rsdicsles of ethylene oxide and propylene oxide or rsdicsles of butylene oxide and v is a number from 2 to 30, or is a mineral or vegetable oil or ester of a mineral or vegetable oil. 15. Composition according to claim 13, characterized in that the penetration enhancer is the vegetable oil ester. 16. Composition according to claim 13, csrscterizsds because the penetration promoter is methyl ester of sceite de colzs. 17. Composition of compliant with co-excipients of claims 13 3 16, characterized in that the content of the penetration enhancer is 1 s 95% by weight. 18. Procedure psrs ls luchs against parasitic insects and / or spider mites, because they are splics uns composition of conformity with cuslquiers of claims 1 to 17 undiluted or diluted on insects and / or spider mites or their habitat in a number of tsl that a csntidsd Effectives of the active principles contained in the insects and / or spider mites or their habitat. 19. Procedure for increasing the effect of phytosanitary products containing a working principle of the class of cyclic ketoenols substituted with phenyl of formula (I) in accordance with claim 2, characterized in that the ready-to-use product (spray liquor) is pre-pressed using a formula (II) in accordance with claim 1. 20. Procedure of conformity with claim 18, characterized in that the spray mixture is pre-spun. with the use of a penetration simulator. 21. Process according to claim 19 or 20, characterized in that the salt of formula (II) is present in a final concentration of 0.5 to 80 mmol / l. 22. Method according to claim 20, characterized in that the penetration enhancer is present in a final concentration of 0.1 to 10 g / 1. 23. Method according to claim 20, characterized in that the penetration facilitator is - present in a final concentration of 0.1 to 10 g / 1 and the salt of formula (II) in a final concentration of 0.5 to 80 mmol / l. 24. Use of a salt of formula (II) of conformity with ls reivindsción 1 psrs the increase of the effect of a phytosanitary product containing a working principle of ls clsse of cyclic ketoenols substituted with phenyl, where ls ssl are used in the prepsession of a Phytosanitary product ready to use psrs (pulverization spray). 25. Use of conformityd with claim 24, wherein the salt of formula (II) is present in the ready-to-use phytosanitary product at a concentration of 0.5 to 80 mmol / l. 26. Use according to claim 24 or 25, wherein the salt is used in prepsession of a ready-to-use phytosubstance product (pulverization spray), which also contains a penetration facilitator.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102005059469.7 | 2005-12-13 |
Publications (1)
Publication Number | Publication Date |
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MX2008007620A true MX2008007620A (en) | 2008-09-26 |
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