FI120340B - Fenyylihydratsiinijohdannaiset, pestisidiset koostumukset ja menetelmä tuholaisten kontrolloimiseksi - Google Patents
Fenyylihydratsiinijohdannaiset, pestisidiset koostumukset ja menetelmä tuholaisten kontrolloimiseksi Download PDFInfo
- Publication number
- FI120340B FI120340B FI942355A FI942355A FI120340B FI 120340 B FI120340 B FI 120340B FI 942355 A FI942355 A FI 942355A FI 942355 A FI942355 A FI 942355A FI 120340 B FI120340 B FI 120340B
- Authority
- FI
- Finland
- Prior art keywords
- alkoxy
- alkyl
- phenyl
- compound
- alkylthio
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 17
- 239000000203 mixture Substances 0.000 title claims description 40
- 230000000361 pesticidal effect Effects 0.000 title claims description 16
- 241000607479 Yersinia pestis Species 0.000 title claims description 13
- 150000004031 phenylhydrazines Chemical class 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 72
- 125000003545 alkoxy group Chemical group 0.000 claims description 67
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 125000001424 substituent group Chemical group 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 18
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 17
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 14
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- -1 substituents halogen Chemical group 0.000 claims description 12
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 10
- 125000002541 furyl group Chemical group 0.000 claims description 10
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 9
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 9
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000001544 thienyl group Chemical group 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 6
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 5
- 239000000575 pesticide Substances 0.000 claims description 5
- 125000001589 carboacyl group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 239000000571 coke Substances 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 241000244206 Nematoda Species 0.000 abstract description 15
- 241000238876 Acari Species 0.000 abstract description 13
- 241000256244 Heliothis virescens Species 0.000 abstract description 6
- 240000007594 Oryza sativa Species 0.000 abstract description 6
- 235000007164 Oryza sativa Nutrition 0.000 abstract description 5
- 235000009566 rice Nutrition 0.000 abstract description 5
- 241001498622 Cixius wagneri Species 0.000 abstract description 2
- 241000489976 Diabrotica undecimpunctata howardi Species 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- 239000000243 solution Substances 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- 238000012360 testing method Methods 0.000 description 15
- 241000196324 Embryophyta Species 0.000 description 12
- 230000000895 acaricidal effect Effects 0.000 description 11
- 238000009472 formulation Methods 0.000 description 11
- 235000013601 eggs Nutrition 0.000 description 10
- 238000007792 addition Methods 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000000642 acaricide Substances 0.000 description 8
- 241000238631 Hexapoda Species 0.000 description 7
- 239000007921 spray Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 239000011550 stock solution Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- 241000488583 Panonychus ulmi Species 0.000 description 4
- 241000194622 Tagosodes orizicolus Species 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000002917 insecticide Substances 0.000 description 4
- 239000002574 poison Substances 0.000 description 4
- 231100000614 poison Toxicity 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000489973 Diabrotica undecimpunctata Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 230000001418 larval effect Effects 0.000 description 3
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- IVRIRQXJSNCSPQ-UHFFFAOYSA-N propan-2-yl carbonochloridate Chemical compound CC(C)OC(Cl)=O IVRIRQXJSNCSPQ-UHFFFAOYSA-N 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 235000011150 stannous chloride Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 3
- DWPDEAOKTWVQEY-UHFFFAOYSA-N (2-methoxydibenzofuran-3-yl)hydrazine Chemical compound O1C2=CC=CC=C2C2=C1C=C(NN)C(OC)=C2 DWPDEAOKTWVQEY-UHFFFAOYSA-N 0.000 description 2
- 244000070406 Malus silvestris Species 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
- 231100000167 toxic agent Toxicity 0.000 description 2
- 239000003440 toxic substance Substances 0.000 description 2
- FUMHZKAOWBEEIU-UHFFFAOYSA-N (2-bromo-5-phenylphenyl)hydrazine Chemical compound C1=C(Br)C(NN)=CC(C=2C=CC=CC=2)=C1 FUMHZKAOWBEEIU-UHFFFAOYSA-N 0.000 description 1
- OXSNTNBZBCGKIB-UHFFFAOYSA-N (2-bromo-5-phenylphenyl)hydrazine;hydrochloride Chemical compound Cl.C1=C(Br)C(NN)=CC(C=2C=CC=CC=2)=C1 OXSNTNBZBCGKIB-UHFFFAOYSA-N 0.000 description 1
- JKOWBWSGMMKFJG-UHFFFAOYSA-N (2-methoxy-5-phenylphenyl)hydrazine;hydrochloride Chemical compound Cl.C1=C(NN)C(OC)=CC=C1C1=CC=CC=C1 JKOWBWSGMMKFJG-UHFFFAOYSA-N 0.000 description 1
- OIIOPWHTJZYKIL-PMACEKPBSA-N (5S)-5-[[[5-[2-chloro-3-[2-chloro-3-[6-methoxy-5-[[[(2S)-5-oxopyrrolidin-2-yl]methylamino]methyl]pyrazin-2-yl]phenyl]phenyl]-3-methoxypyrazin-2-yl]methylamino]methyl]pyrrolidin-2-one Chemical compound C1(=C(N=C(C2=C(C(C3=CC=CC(=C3Cl)C3=NC(OC)=C(N=C3)CNC[C@H]3NC(=O)CC3)=CC=C2)Cl)C=N1)OC)CNC[C@H]1NC(=O)CC1 OIIOPWHTJZYKIL-PMACEKPBSA-N 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical compound C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 1
- RHDYQUZYHZWTCI-UHFFFAOYSA-N 1-methoxy-4-phenylbenzene Chemical compound C1=CC(OC)=CC=C1C1=CC=CC=C1 RHDYQUZYHZWTCI-UHFFFAOYSA-N 0.000 description 1
- JDTMUJBWSGNMGR-UHFFFAOYSA-N 1-nitro-4-phenoxybenzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=CC=C1 JDTMUJBWSGNMGR-UHFFFAOYSA-N 0.000 description 1
- XXMFJKNOJSDQBM-UHFFFAOYSA-N 2,2,2-trifluoroacetic acid;hydrate Chemical compound [OH3+].[O-]C(=O)C(F)(F)F XXMFJKNOJSDQBM-UHFFFAOYSA-N 0.000 description 1
- OGYBXNHWTBBAKW-UHFFFAOYSA-N 2-bromo-5-phenylaniline Chemical compound C1=C(Br)C(N)=CC(C=2C=CC=CC=2)=C1 OGYBXNHWTBBAKW-UHFFFAOYSA-N 0.000 description 1
- DTYBRSLINXBXMP-UHFFFAOYSA-N 2-methoxy-5-phenylaniline Chemical compound C1=C(N)C(OC)=CC=C1C1=CC=CC=C1 DTYBRSLINXBXMP-UHFFFAOYSA-N 0.000 description 1
- SGQVWNYSHWQNOS-UHFFFAOYSA-N 2-methoxydibenzofuran-3-amine Chemical compound O1C2=CC=CC=C2C2=C1C=C(N)C(OC)=C2 SGQVWNYSHWQNOS-UHFFFAOYSA-N 0.000 description 1
- PZVOYRGZHNJDAY-UHFFFAOYSA-N 5-phenyloxadiazol-4-one Chemical class O=C1N=NOC1C1=CC=CC=C1 PZVOYRGZHNJDAY-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical class CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 1
- 244000144725 Amygdalus communis Species 0.000 description 1
- 244000144730 Amygdalus persica Species 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- YYTBOAALEHZZKV-UHFFFAOYSA-N C1=C(OC)C(NNC(=O)CC)=CC(C=2C=CC=CC=2)=C1 Chemical compound C1=C(OC)C(NNC(=O)CC)=CC(C=2C=CC=CC=2)=C1 YYTBOAALEHZZKV-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- JLVQMBSACVQFHU-UHFFFAOYSA-N Cl.NN.BrC1=CC=C(C=C1)C1=CC=CC=C1 Chemical compound Cl.NN.BrC1=CC=C(C=C1)C1=CC=CC=C1 JLVQMBSACVQFHU-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 244000000626 Daucus carota Species 0.000 description 1
- 235000002767 Daucus carota Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 101150056422 Krt1 gene Proteins 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 235000011430 Malus pumila Nutrition 0.000 description 1
- 235000015103 Malus silvestris Nutrition 0.000 description 1
- 240000004658 Medicago sativa Species 0.000 description 1
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 1
- 241000243786 Meloidogyne incognita Species 0.000 description 1
- 241000243785 Meloidogyne javanica Species 0.000 description 1
- 101100457407 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) mmm-1 gene Proteins 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- JLNTWVDSQRNWFU-UHFFFAOYSA-N OOOOOOO Chemical compound OOOOOOO JLNTWVDSQRNWFU-UHFFFAOYSA-N 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 244000042314 Vigna unguiculata Species 0.000 description 1
- 241000219094 Vitaceae Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 235000020224 almond Nutrition 0.000 description 1
- BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 235000021016 apples Nutrition 0.000 description 1
- 239000012223 aqueous fraction Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- BJXYHBKEQFQVES-NWDGAFQWSA-N enpatoran Chemical compound N[C@H]1CN(C[C@H](C1)C(F)(F)F)C1=C2C=CC=NC2=C(C=C1)C#N BJXYHBKEQFQVES-NWDGAFQWSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- OWIUPIRUAQMTTK-UHFFFAOYSA-M n-aminocarbamate Chemical compound NNC([O-])=O OWIUPIRUAQMTTK-UHFFFAOYSA-M 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 101150093727 sspO gene Proteins 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000012876 topography Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/28—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group; Thio analogues thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/30—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the groups —CO—N< and, both being directly attached by their carbon atoms to the same carbon skeleton, e.g. H2N—NH—CO—C6H4—COOCH3; Thio-analogues thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds
- A01N57/30—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds containing aromatic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
- C07C243/26—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C243/28—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of a saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/02—Compounds containing any of the groups, e.g. carbazates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/06—Compounds containing any of the groups, e.g. semicarbazides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/48—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups having nitrogen atoms of sulfonamide groups further bound to another hetero atom
- C07C311/49—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups having nitrogen atoms of sulfonamide groups further bound to another hetero atom to nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C337/00—Derivatives of thiocarbonic acids containing functional groups covered by groups C07C333/00 or C07C335/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C337/02—Compounds containing any of the groups, e.g. thiocarbazates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2479—Compounds containing the structure P(=X)n-N-acyl, P(=X)n-N-heteroatom, P(=X)n-N-CN (X = O, S, Se; n = 0, 1)
- C07F9/2491—Compounds containing the structure P(=X)n-N-acyl, P(=X)n-N-heteroatom, P(=X)n-N-CN (X = O, S, Se; n = 0, 1) containing the structure P(=X)n-N-N (X = O, S, Se; n = 0, 1)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US79650691A | 1991-11-22 | 1991-11-22 | |
US79650691 | 1991-11-22 | ||
PCT/US1992/009855 WO1993010083A1 (en) | 1991-11-22 | 1992-11-17 | Insecticidal phenylhydrazine derivatives |
US9209855 | 1992-11-17 |
Publications (3)
Publication Number | Publication Date |
---|---|
FI942355A0 FI942355A0 (fi) | 1994-05-20 |
FI942355A FI942355A (fi) | 1994-07-20 |
FI120340B true FI120340B (fi) | 2009-09-30 |
Family
ID=25168348
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FI942355A FI120340B (fi) | 1991-11-22 | 1994-05-20 | Fenyylihydratsiinijohdannaiset, pestisidiset koostumukset ja menetelmä tuholaisten kontrolloimiseksi |
Country Status (22)
Country | Link |
---|---|
US (1) | US5367093A (pt) |
EP (1) | EP0641316B1 (pt) |
JP (1) | JP2552811B2 (pt) |
KR (1) | KR100235246B1 (pt) |
CN (1) | CN1033699C (pt) |
AT (1) | ATE148104T1 (pt) |
AU (1) | AU670927B2 (pt) |
BR (1) | BR9206803A (pt) |
CA (1) | CA2123885C (pt) |
DE (1) | DE69217085T2 (pt) |
DK (1) | DK0641316T3 (pt) |
ES (1) | ES2097372T3 (pt) |
FI (1) | FI120340B (pt) |
GR (1) | GR3023097T3 (pt) |
HU (1) | HU219189B (pt) |
IL (1) | IL103828A (pt) |
PL (1) | PL171968B1 (pt) |
RO (1) | RO112860B1 (pt) |
TW (1) | TW234075B (pt) |
UA (1) | UA41298C2 (pt) |
WO (1) | WO1993010083A1 (pt) |
ZA (1) | ZA928915B (pt) |
Families Citing this family (62)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5543404A (en) * | 1995-07-05 | 1996-08-06 | Uniroyal Chemical Company, Inc | Pesticidal phenylhydrazinephosphates |
US5567723A (en) * | 1995-07-05 | 1996-10-22 | Uniroyal Chemical Company, Inc. | Miticidal hydrazine compounds and their intermediates |
FR2754254B1 (fr) * | 1996-10-09 | 1998-10-30 | Rhone Poulenc Agrochimie | Fongicides a groupes hydroximiques et hydrazoniques |
US5874465A (en) * | 1996-10-24 | 1999-02-23 | Uniroyal Chemical Company, Inc. | Hydrazinecarboxylate miticides and insecticides |
IL132868A0 (en) * | 1998-11-24 | 2001-03-19 | Rohm & Haas | Phosphoryl hydrazine insecticides |
US6242647B1 (en) | 1998-12-03 | 2001-06-05 | American Cyanamid Company | Insecticidal biphenylthiohydrazides |
US6297275B1 (en) | 1999-09-07 | 2001-10-02 | Uniroyal Chemical Company, Inc. | Method for controlling fungi using phenylhydrazine derivatives |
US6093843A (en) * | 1999-10-06 | 2000-07-25 | Uniroyal Chemical Company, Inc. | 4-hydroxybiphenyl hydrazide derivatives |
US6278022B1 (en) * | 1999-11-01 | 2001-08-21 | Ck Witco Corporation | Process for the preparation of insecticidal phenylhydrazine derivatives |
US6166243A (en) * | 1999-11-01 | 2000-12-26 | Ck Witco Corporation | Process for the preparation of insecticidal phenylhydrazine derivatives |
DE19953775A1 (de) | 1999-11-09 | 2001-05-10 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
DE10007411A1 (de) * | 2000-02-18 | 2001-08-23 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
DE10013914A1 (de) | 2000-03-21 | 2001-09-27 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
DE10015310A1 (de) * | 2000-03-28 | 2001-10-04 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
DE10017881A1 (de) * | 2000-04-11 | 2001-10-25 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
DE10018370A1 (de) * | 2000-04-14 | 2001-10-18 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
DE10024934A1 (de) | 2000-05-19 | 2001-11-22 | Bayer Ag | Wirkstoffkombinationen mit insektiziden akariziden Eigenschaften |
DE10042736A1 (de) | 2000-08-31 | 2002-03-14 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
DE10043610A1 (de) * | 2000-09-05 | 2002-03-14 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
DE10055941A1 (de) * | 2000-11-10 | 2002-05-23 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
DE10059606A1 (de) | 2000-12-01 | 2002-06-06 | Bayer Ag | Wirkstoffkombinationen |
DE10248257A1 (de) * | 2002-10-16 | 2004-04-29 | Bayer Cropscience Ag | Wirkstoffkombinationen im insektiziden und akariziden Eigenschaften |
US6706895B1 (en) | 2002-11-14 | 2004-03-16 | Uniroyal Chemical Company, Inc. | 4-methoxybiphenyl hydrazone derivatives |
DE10319591A1 (de) | 2003-05-02 | 2004-11-18 | Bayer Cropscience Ag | Wirkstoffkombinationen mit nematiziden, insektiziden und fungiziden Eigenschaften basierend auf Trifluorbutenyl-Verbindungen |
DE10319590A1 (de) | 2003-05-02 | 2004-11-18 | Bayer Cropscience Ag | Wirkstoffkombinationen mit nematiziden und insektiziden Eigenschaften basierend auf Trifluorbutenyl-Verbindungen |
US7343196B2 (en) * | 2003-05-09 | 2008-03-11 | Ge Medical Systems Global Technology Company Llc | Cardiac CT system and method for planning and treatment of biventricular pacing using epicardial lead |
EP2385037A1 (en) * | 2003-06-24 | 2011-11-09 | Chemtura Corporation | Fungicidal phenoxyphenylhydrazine derivatives |
DE10330724A1 (de) | 2003-07-08 | 2005-01-27 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
DE10330723A1 (de) * | 2003-07-08 | 2005-02-03 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
DE10353281A1 (de) | 2003-11-14 | 2005-06-16 | Bayer Cropscience Ag | Wirkstoffkombination mit insektiziden und akariziden Eigenschaften |
DE102004021564A1 (de) | 2003-11-14 | 2005-07-07 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden Eigenschaften |
AU2004294259C1 (en) | 2003-12-04 | 2014-07-10 | Bayer Cropscience Aktiengesellschaft | Active substance combination having insecticidal and acaricidal properties |
CA2547989C (en) | 2003-12-04 | 2012-10-09 | Bayer Cropscience Ag | Active substance combinations having insecticidal properties |
DE10356550A1 (de) | 2003-12-04 | 2005-07-07 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden Eigenschaften |
DE102004001271A1 (de) | 2004-01-08 | 2005-08-04 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden Eigenschaften |
JP2006076990A (ja) | 2004-03-12 | 2006-03-23 | Bayer Cropscience Ag | 殺虫性ベンゼンジカルボキサミド類 |
US7592374B2 (en) * | 2005-03-03 | 2009-09-22 | Crompton Corporation | Insecticidal nitromethylene compounds |
US7446119B2 (en) * | 2005-03-28 | 2008-11-04 | Crompton Corporation | Miticidal triazolidine derivatives |
DE102005022147A1 (de) | 2005-04-28 | 2006-11-02 | Bayer Cropscience Ag | Wirkstoffkombinationen |
DE102006056544A1 (de) | 2006-11-29 | 2008-06-05 | Bayer Cropscience Ag | Insektizide Wirkstoffkombinationen (Formononetin+Insektizide) |
US7511029B2 (en) * | 2007-05-16 | 2009-03-31 | Chemtura Corporation | Pesticidal diazene oxide carboxylates |
BRPI0811140B1 (pt) * | 2007-05-22 | 2022-08-16 | Wyeth Llc | Processos melhorados para produção de hidrazidas |
EP2008517A1 (de) | 2007-06-29 | 2008-12-31 | Bayer CropScience AG | Akarizide Wirkstoffkombinationen |
DE102007045922A1 (de) | 2007-09-26 | 2009-04-02 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
US8404260B2 (en) | 2008-04-02 | 2013-03-26 | Bayer Cropscience Lp | Synergistic pesticide compositions |
EP2127522A1 (de) | 2008-05-29 | 2009-12-02 | Bayer CropScience AG | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
PE20121693A1 (es) | 2010-01-22 | 2012-12-01 | Bayer Ip Gmbh | Combinacion de espiromesifeno y abamectina como insecticidas |
EP2382865A1 (de) | 2010-04-28 | 2011-11-02 | Bayer CropScience AG | Synergistische Wirkstoffkombinationen |
CN102344395A (zh) * | 2011-07-28 | 2012-02-08 | 同济大学 | 一种联苯肼酯的合成方法 |
JP5790533B2 (ja) * | 2012-02-14 | 2015-10-07 | 住友化学株式会社 | フェニルヒドラジン−β−カルボキシレート化合物の精製方法 |
CN105638671B (zh) * | 2012-05-05 | 2018-05-18 | 陕西美邦农药有限公司 | 一种高效农药组合物 |
CN103380783B (zh) * | 2012-05-05 | 2016-04-27 | 陕西美邦农药有限公司 | 一种高效农药组合物 |
CN102885074B (zh) * | 2012-11-06 | 2013-12-11 | 江苏辉丰农化股份有限公司 | 具有增效作用的杀螨剂组合物 |
CN102986696A (zh) * | 2012-12-24 | 2013-03-27 | 海利尔药业集团股份有限公司 | 一种含有嘧螨酯与联苯肼酯的杀螨组合物 |
CN103039511B (zh) * | 2012-12-25 | 2014-01-08 | 北京市农林科学院 | 一种含联苯肼酯与毒死蜱的增效杀螨组合物 |
CN103004864B (zh) * | 2013-01-10 | 2014-02-19 | 北京市农林科学院 | 一种含有联苯肼酯与辛硫磷的农药组合物 |
CN104082322B (zh) * | 2014-06-19 | 2017-01-04 | 广东中迅农科股份有限公司 | 一种含有吡丙醚和联苯肼酯的杀虫杀螨组合物 |
CN110818596A (zh) * | 2019-11-18 | 2020-02-21 | 合肥锦绣田园化工科技有限公司 | 一种氨基脲类化合物及其制备与应用 |
CR20230186A (es) | 2020-09-30 | 2023-08-24 | Control Solutions Inc | Composiciones en polvo para el control de plagas y métodos de uso |
US20220272980A1 (en) | 2021-03-01 | 2022-09-01 | Control Solutions, Inc. | Solid particulate pest control compositions and methods |
CN115677540B (zh) * | 2021-07-23 | 2023-11-10 | 帕潘纳(北京)科技有限公司 | 一种联苯肼酯的制备方法 |
CN115197103A (zh) * | 2022-06-01 | 2022-10-18 | 浙江农林大学 | 偶氮类化合物或氧化偶氮类化合物、其农林业上适用的盐、它们的组合物,及其制备和应用 |
Family Cites Families (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2272047A (en) * | 1940-07-02 | 1942-02-03 | Henry A Wallace | Insecticide |
US2403495A (en) * | 1942-02-10 | 1946-07-09 | Nasa | Insecticide |
US2572867A (en) * | 1949-02-25 | 1951-10-30 | Karel Leonard | Rodenticide comprising fluoroacetphenylhydrazide |
DE1567157C3 (de) * | 1965-09-14 | 1974-10-03 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Carbonsäurehydrazide, Verfahren zu deren Herstellung, sowie deren Verwendung als Saatgutbehandlungsmittel |
DE1767924A1 (de) * | 1968-07-02 | 1971-10-07 | Bayer Ag | 1-Phenyl-4,4-dialkyl-thiosemicarbazide |
US3919247A (en) * | 1970-09-14 | 1975-11-11 | Lodzkie Zaklady Farma | Method of manufacturing of indolyl acetic acids |
BE789780A (fr) * | 1971-10-08 | 1973-02-01 | Minnesota Mining & Mfg | Emulsions photographiques a base d'halogenure d'argent et leur preparation |
JPS54136821A (en) * | 1978-04-17 | 1979-10-24 | Konishiroku Photo Ind Co Ltd | Sliver halide photosensitive material |
JPS5564557A (en) * | 1978-11-08 | 1980-05-15 | Mitsui Toatsu Chem Inc | Diphenyl ether compound and herbicide containing the same |
IT1149844B (it) * | 1980-10-03 | 1986-12-10 | Montedison Spa | Carbazati fungicidi |
DE3267258D1 (en) * | 1981-06-15 | 1985-12-12 | Shell Int Research | 7-substituted 2,3-dihydrobenzofurans, their preparation and their use as pesticides or as chemical intermediates |
US4514419A (en) * | 1982-05-06 | 1985-04-30 | Fmc Corporation | Nematicidal use of hydrazinecarboxamides and carbothioamides |
US4638088A (en) * | 1984-11-15 | 1987-01-20 | Union Carbide Corporation | Pesticidal biphenylyloxy and biphenylylalkoxy aryl acyl urea compounds |
US4725302A (en) * | 1984-11-27 | 1988-02-16 | Ciba-Geigy Corporation | Substituted phenylhydrazines and phenyloxadiazolinones and pesticidal usage thereof |
US5237099A (en) * | 1985-12-09 | 1993-08-17 | American Cyanamid Company | Insecticidal substituted and unsubstituted benzoic acid 1-alkyl, 2-alkyl and 2-cycloalkylhydrazides |
US5225443A (en) * | 1986-05-01 | 1993-07-06 | Rohm And Haas Company | Insecticidal N'-substituted-N'-substituted N,N'-diacylhydrazines |
CA2012004A1 (en) * | 1989-03-15 | 1990-09-15 | Frank Ellis | Chemical compounds |
DE4015834A1 (de) * | 1990-05-17 | 1991-11-21 | Bayer Ag | Phenoxyphenylsulfonylverbindungen |
-
1992
- 1992-11-17 AU AU31374/93A patent/AU670927B2/en not_active Expired
- 1992-11-17 DK DK92925247.6T patent/DK0641316T3/da active
- 1992-11-17 PL PL92303793A patent/PL171968B1/pl unknown
- 1992-11-17 WO PCT/US1992/009855 patent/WO1993010083A1/en active IP Right Grant
- 1992-11-17 ES ES92925247T patent/ES2097372T3/es not_active Expired - Lifetime
- 1992-11-17 AT AT92925247T patent/ATE148104T1/de active
- 1992-11-17 KR KR1019940701712A patent/KR100235246B1/ko not_active IP Right Cessation
- 1992-11-17 JP JP5509447A patent/JP2552811B2/ja not_active Expired - Lifetime
- 1992-11-17 DE DE69217085T patent/DE69217085T2/de not_active Expired - Lifetime
- 1992-11-17 HU HU9401552A patent/HU219189B/hu unknown
- 1992-11-17 EP EP92925247A patent/EP0641316B1/en not_active Expired - Lifetime
- 1992-11-17 RO RO94-00851A patent/RO112860B1/ro unknown
- 1992-11-17 BR BR9206803A patent/BR9206803A/pt not_active IP Right Cessation
- 1992-11-17 TW TW081109184A patent/TW234075B/zh active
- 1992-11-17 CA CA002123885A patent/CA2123885C/en not_active Expired - Lifetime
- 1992-11-17 UA UA94005513A patent/UA41298C2/uk unknown
- 1992-11-18 ZA ZA928915A patent/ZA928915B/xx unknown
- 1992-11-20 IL IL10382892A patent/IL103828A/xx not_active IP Right Cessation
- 1992-11-20 US US07/979,095 patent/US5367093A/en not_active Expired - Lifetime
- 1992-11-21 CN CN92114622A patent/CN1033699C/zh not_active Expired - Lifetime
-
1994
- 1994-05-20 FI FI942355A patent/FI120340B/fi not_active IP Right Cessation
-
1997
- 1997-04-10 GR GR970400759T patent/GR3023097T3/el unknown
Also Published As
Publication number | Publication date |
---|---|
US5367093A (en) | 1994-11-22 |
HU9401552D0 (en) | 1994-09-28 |
KR100235246B1 (ko) | 1999-12-15 |
JP2552811B2 (ja) | 1996-11-13 |
BR9206803A (pt) | 1995-05-02 |
EP0641316B1 (en) | 1997-01-22 |
HU219189B (hu) | 2001-02-28 |
DE69217085D1 (de) | 1997-03-06 |
CA2123885A1 (en) | 1993-05-27 |
GR3023097T3 (en) | 1997-07-30 |
CN1033699C (zh) | 1997-01-01 |
ES2097372T3 (es) | 1997-04-01 |
DK0641316T3 (da) | 1997-08-11 |
ZA928915B (en) | 1993-08-06 |
DE69217085T2 (de) | 1997-05-28 |
FI942355A0 (fi) | 1994-05-20 |
JPH07502267A (ja) | 1995-03-09 |
AU670927B2 (en) | 1996-08-08 |
TW234075B (pt) | 1994-11-11 |
CN1075952A (zh) | 1993-09-08 |
IL103828A0 (en) | 1993-04-04 |
EP0641316A1 (en) | 1995-03-08 |
UA41298C2 (uk) | 2001-09-17 |
HUT68639A (en) | 1995-07-28 |
FI942355A (fi) | 1994-07-20 |
ATE148104T1 (de) | 1997-02-15 |
AU3137493A (en) | 1993-06-15 |
RO112860B1 (ro) | 1998-01-30 |
CA2123885C (en) | 2004-03-30 |
WO1993010083A1 (en) | 1993-05-27 |
PL171968B1 (pl) | 1997-07-31 |
IL103828A (en) | 1997-01-10 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
FI120340B (fi) | Fenyylihydratsiinijohdannaiset, pestisidiset koostumukset ja menetelmä tuholaisten kontrolloimiseksi | |
RU2109730C1 (ru) | Фенилгидразиновые производные, способ борьбы с вредителями и инсектоакарицидонематоцидная композиция | |
PL156233B1 (en) | Agent for fighting against harmflul insects or microorganisms or preventing an injurious attack by them | |
FI98912C (fi) | Mikrobisidiset 2-anilino-pyrimidiinijohdannaiset | |
PL112140B1 (en) | Insecticide | |
PL78373B1 (en) | 3-(3{40 ,5{40 -dihalogenophenyl)imidazolidine-2,4-dione derivatives [us3668217a] | |
CS272770B2 (en) | Fungicide and method of active substances production | |
PL167500B1 (pl) | Srodek grzybobójczy PL PL | |
HU187389B (en) | Herbicide compositions and process for preparing tiazoline derivatives | |
CS241078B2 (en) | Microbicide for plants' diseases suppression and method of active substances production | |
PT818144E (pt) | Microbicida | |
PL132245B1 (en) | Agent for controlling and/or protection against paralysis by harmfuk microorganisms and method of manufacture of novel derivatives of arylamines | |
US4687861A (en) | Microbicidal compositions | |
AU2015238574B2 (en) | Phenylpiperidinecarboxamide derivatives as fungicides | |
JPH0421672B2 (pt) | ||
US2835625A (en) | Isopropoxycarbonyl dimethyldithio-carbamate | |
AU735932B2 (en) | Agricultural and horticultural fungicidal compositions | |
CS411386A2 (en) | Fungicide and method of its active substances production | |
PL154973B1 (en) | Fungicide | |
JP2002363164A (ja) | ピラゾールカルボキサミド類、その中間体およびこれを有効成分とする有害生物防除剤 | |
US4100281A (en) | Mono-5-substituted-thio-3-chloro-4H-1,2,6-thiadiazin-4-one antifungal agents | |
KR100417794B1 (ko) | 농약용옥사디아진 | |
CA1256869A (en) | 2-cyano-3-phenyl-4-nitrobutenamines | |
UA125364C2 (uk) | Похідна тіофенкарбоксаміду й засіб для контролю захворювання рослин, що містить її | |
KR800001547B1 (ko) | 티아졸일 신나민산 니트릴류의 제조방법 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
GB | Transfer or assigment of application |
Owner name: UNIROYAL CHEMICAL COMPANY, INC. |
|
FG | Patent granted |
Ref document number: 120340 Country of ref document: FI |
|
MA | Patent expired |