US20010046994A1 - Hexahydrotriazine compounds and insecticides - Google Patents
Hexahydrotriazine compounds and insecticides Download PDFInfo
- Publication number
- US20010046994A1 US20010046994A1 US09/729,865 US72986500A US2001046994A1 US 20010046994 A1 US20010046994 A1 US 20010046994A1 US 72986500 A US72986500 A US 72986500A US 2001046994 A1 US2001046994 A1 US 2001046994A1
- Authority
- US
- United States
- Prior art keywords
- chloro
- nitroiminohexahydro
- triazine
- compound
- pyridylmethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000002917 insecticide Substances 0.000 title claims description 27
- OYWRDHBGMCXGFY-UHFFFAOYSA-N 1,2,3-triazinane Chemical class C1CNNNC1 OYWRDHBGMCXGFY-UHFFFAOYSA-N 0.000 title abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 66
- -1 amine compound Chemical class 0.000 claims abstract description 23
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229930040373 Paraformaldehyde Natural products 0.000 claims abstract description 3
- 229920002866 paraformaldehyde Polymers 0.000 claims abstract description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- NRPCZWUIOZTKHN-UHFFFAOYSA-N n-[1-[(2-chloro-1,3-thiazol-5-yl)methyl]-3,5-dimethyl-1,3,5-triazinan-2-ylidene]nitramide Chemical compound C1N(C)CN(C)C(=N[N+]([O-])=O)N1CC1=CN=C(Cl)S1 NRPCZWUIOZTKHN-UHFFFAOYSA-N 0.000 claims description 3
- JSQALCOPVQFHFG-UHFFFAOYSA-N n-[1-[(6-chloropyridin-3-yl)methyl]-3,5-dimethyl-1,3,5-triazinan-2-ylidene]nitramide Chemical compound C1N(C)CN(C)C(=N[N+]([O-])=O)N1CC1=CC=C(Cl)N=C1 JSQALCOPVQFHFG-UHFFFAOYSA-N 0.000 claims description 3
- NOJNNNIXCNEEPT-UHFFFAOYSA-N n-[1-[(6-chloropyridin-3-yl)methyl]-3-ethyl-2,4-dihydro-1,3,5-triazin-6-yl]nitramide Chemical compound C1N(CC)CNC(=N[N+]([O-])=O)N1CC1=CC=C(Cl)N=C1 NOJNNNIXCNEEPT-UHFFFAOYSA-N 0.000 claims description 3
- YMAYNUXAPXZOQS-UHFFFAOYSA-N n-[1-[(6-chloropyridin-3-yl)methyl]-3-methyl-2,4-dihydro-1,3,5-triazin-6-yl]nitramide Chemical compound C1N(C)CNC(=N[N+]([O-])=O)N1CC1=CC=C(Cl)N=C1 YMAYNUXAPXZOQS-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- XSXHWVKGUXMUQE-UHFFFAOYSA-N osmium dioxide Inorganic materials O=[Os]=O XSXHWVKGUXMUQE-UHFFFAOYSA-N 0.000 claims description 2
- BOVITRBKHRZMIL-UHFFFAOYSA-N n-[1,3-bis[(6-chloropyridin-3-yl)methyl]-1,3,5-triazinan-2-ylidene]nitramide Chemical compound C1NCN(CC=2C=NC(Cl)=CC=2)C(=N[N+](=O)[O-])N1CC1=CC=C(Cl)N=C1 BOVITRBKHRZMIL-UHFFFAOYSA-N 0.000 claims 2
- LMYUREBWNXOTBY-UHFFFAOYSA-N n-[1-[(2-chloro-1,3-thiazol-5-yl)methyl]-5-methyl-3-propyl-1,3,5-triazinan-2-ylidene]nitramide Chemical compound [O-][N+](=O)N=C1N(CCC)CN(C)CN1CC1=CN=C(Cl)S1 LMYUREBWNXOTBY-UHFFFAOYSA-N 0.000 claims 2
- UKMXUOCNWDRAPK-UHFFFAOYSA-N n-[1-[(6-chloropyridin-3-yl)methyl]-3-ethyl-5-methyl-1,3,5-triazinan-2-ylidene]nitramide Chemical compound [O-][N+](=O)N=C1N(CC)CN(C)CN1CC1=CC=C(Cl)N=C1 UKMXUOCNWDRAPK-UHFFFAOYSA-N 0.000 claims 2
- MLTJSOKVOGKDOW-UHFFFAOYSA-N n-[1-[(6-chloropyridin-3-yl)methyl]-3-propan-2-yl-2,4-dihydro-1,3,5-triazin-6-yl]nitramide Chemical compound C1N(C(C)C)CNC(=N[N+]([O-])=O)N1CC1=CC=C(Cl)N=C1 MLTJSOKVOGKDOW-UHFFFAOYSA-N 0.000 claims 2
- ZHXIZSSJURBKED-UHFFFAOYSA-N n-[1-[(6-chloropyridin-3-yl)methyl]-5-methyl-3-prop-2-ynyl-1,3,5-triazinan-2-ylidene]nitramide Chemical compound C1N(C)CN(CC#C)C(=N[N+]([O-])=O)N1CC1=CC=C(Cl)N=C1 ZHXIZSSJURBKED-UHFFFAOYSA-N 0.000 claims 2
- DBMKGDMBMHNJPG-UHFFFAOYSA-N n-[1-[(6-chloropyridin-3-yl)methyl]-5-methyl-3-propyl-1,3,5-triazinan-2-ylidene]nitramide Chemical compound [O-][N+](=O)N=C1N(CCC)CN(C)CN1CC1=CC=C(Cl)N=C1 DBMKGDMBMHNJPG-UHFFFAOYSA-N 0.000 claims 2
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 20
- 0 *N1CN(C)C(=N[N+](=O)[O-])N(C)C1.C Chemical compound *N1CN(C)C(=N[N+](=O)[O-])N(C)C1.C 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 241000238631 Hexapoda Species 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 8
- RTEUDRWHKUPKJB-UHFFFAOYSA-N CC1=CN=C(Cl)S1 Chemical compound CC1=CN=C(Cl)S1 RTEUDRWHKUPKJB-UHFFFAOYSA-N 0.000 description 7
- HJQDSJJSRDWZIA-UHFFFAOYSA-N CCc1ccc(Cl)nc1 Chemical compound CCc1ccc(Cl)nc1 HJQDSJJSRDWZIA-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XVAZLPCERHSKCI-UHFFFAOYSA-N CC1=CN=C(Cl)S1.Cc1ccc(Cl)nc1 Chemical compound CC1=CN=C(Cl)S1.Cc1ccc(Cl)nc1 XVAZLPCERHSKCI-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 241000251468 Actinopterygii Species 0.000 description 5
- 241000238424 Crustacea Species 0.000 description 5
- 231100000674 Phytotoxicity Toxicity 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 231100000419 toxicity Toxicity 0.000 description 5
- 230000001988 toxicity Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VXLYOURCUVQYLN-UHFFFAOYSA-N Cc1ccc(Cl)nc1 Chemical compound Cc1ccc(Cl)nc1 VXLYOURCUVQYLN-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 241000209094 Oryza Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- 239000004563 wettable powder Substances 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 230000000749 insecticidal effect Effects 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- YUSXGLYXEBLNTO-UHFFFAOYSA-N 1-chloro-n-(chloromethyl)-n-methylmethanamine Chemical compound ClCN(C)CCl YUSXGLYXEBLNTO-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- GHBBFPGYBPOUCF-UHFFFAOYSA-N 2-[(6-chloropyridin-3-yl)methyl]-1-nitroguanidine Chemical compound [O-][N+](=O)NC(=N)NCC1=CC=C(Cl)N=C1 GHBBFPGYBPOUCF-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- SVJZPKNAZAWOIK-UHFFFAOYSA-N C.CCc1ccc(Cl)nc1 Chemical compound C.CCc1ccc(Cl)nc1 SVJZPKNAZAWOIK-UHFFFAOYSA-N 0.000 description 2
- 241000254173 Coleoptera Species 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 241000255925 Diptera Species 0.000 description 2
- 241000258937 Hemiptera Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- ORMNPCYEYRVQIF-UHFFFAOYSA-N II.[H]N(C)/C(=N\[N+](=O)[O-])N([H])CC Chemical compound II.[H]N(C)/C(=N\[N+](=O)[O-])N([H])CC ORMNPCYEYRVQIF-UHFFFAOYSA-N 0.000 description 2
- 241000256602 Isoptera Species 0.000 description 2
- 241000255777 Lepidoptera Species 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 241000358422 Nephotettix cincticeps Species 0.000 description 2
- 241000238814 Orthoptera Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000007605 air drying Methods 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- LRCFXGAMWKDGLA-UHFFFAOYSA-N dioxosilane;hydrate Chemical compound O.O=[Si]=O LRCFXGAMWKDGLA-UHFFFAOYSA-N 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- SCAWPDJOSHEKLT-UHFFFAOYSA-N n-(1,3-dimethyl-2,4-dihydro-1,3,5-triazin-6-yl)nitramide Chemical compound CN1CN=C(N[N+]([O-])=O)N(C)C1 SCAWPDJOSHEKLT-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- VRMUIVKEHJSADG-UHFFFAOYSA-N 2-chloro-5-(chloromethyl)-1,3-thiazole Chemical compound ClCC1=CN=C(Cl)S1 VRMUIVKEHJSADG-UHFFFAOYSA-N 0.000 description 1
- SKCNYHLTRZIINA-UHFFFAOYSA-N 2-chloro-5-(chloromethyl)pyridine Chemical compound ClCC1=CC=C(Cl)N=C1 SKCNYHLTRZIINA-UHFFFAOYSA-N 0.000 description 1
- 241000175828 Adoxophyes orana Species 0.000 description 1
- 241000218475 Agrotis segetum Species 0.000 description 1
- 241000519878 Anomala rufocuprea Species 0.000 description 1
- 241001600408 Aphis gossypii Species 0.000 description 1
- 241000902805 Aulacophora Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 241000238657 Blattella germanica Species 0.000 description 1
- OIHBXLZSYJNYJD-UHFFFAOYSA-N C.CC1=CN=C(Cl)S1.Cc1ccc(Cl)nc1 Chemical compound C.CC1=CN=C(Cl)S1.Cc1ccc(Cl)nc1 OIHBXLZSYJNYJD-UHFFFAOYSA-N 0.000 description 1
- FLIMMSMIDLDGKQ-UHFFFAOYSA-N CC(CC1)C=NC1Cl Chemical compound CC(CC1)C=NC1Cl FLIMMSMIDLDGKQ-UHFFFAOYSA-N 0.000 description 1
- YWJDNZHLVSPUEZ-UHFFFAOYSA-N CCCC(CC)(CC(CC)CN1)C1Cl Chemical compound CCCC(CC)(CC(CC)CN1)C1Cl YWJDNZHLVSPUEZ-UHFFFAOYSA-N 0.000 description 1
- DENJWAZBLGVDOB-UHFFFAOYSA-N CCN/C(=N/[N+](=O)[O-])NC Chemical compound CCN/C(=N/[N+](=O)[O-])NC DENJWAZBLGVDOB-UHFFFAOYSA-N 0.000 description 1
- SBACTGQSQURQPI-UHFFFAOYSA-N COS(=O)Oc1ccc(C)cc1 Chemical compound COS(=O)Oc1ccc(C)cc1 SBACTGQSQURQPI-UHFFFAOYSA-N 0.000 description 1
- MHRYQUKHWOXDFI-UHFFFAOYSA-N Cc1cc(OP(C)(C)=S)ccc1[N+](=O)[O-].O.O Chemical compound Cc1cc(OP(C)(C)=S)ccc1[N+](=O)[O-].O.O MHRYQUKHWOXDFI-UHFFFAOYSA-N 0.000 description 1
- DZBLBGNHEHPISC-UHFFFAOYSA-N Cc1ccc(O[SH](=O)=O)cc1 Chemical compound Cc1ccc(O[SH](=O)=O)cc1 DZBLBGNHEHPISC-UHFFFAOYSA-N 0.000 description 1
- 241000426497 Chilo suppressalis Species 0.000 description 1
- 241001498622 Cixius wagneri Species 0.000 description 1
- 241000098289 Cnaphalocrocis medinalis Species 0.000 description 1
- 241001509962 Coptotermes formosanus Species 0.000 description 1
- 241000256059 Culex pipiens Species 0.000 description 1
- 241000785585 Gryllotalpa africana Species 0.000 description 1
- 241001299253 Henosepilachna vigintioctopunctata Species 0.000 description 1
- 241000282414 Homo sapiens Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241001470017 Laodelphax striatella Species 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 241000272317 Lipaphis erysimi Species 0.000 description 1
- 241000966204 Lissorhoptrus oryzophilus Species 0.000 description 1
- 241000254022 Locusta migratoria Species 0.000 description 1
- 241000555303 Mamestra brassicae Species 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- 241000721621 Myzus persicae Species 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- LIWAQLJGPBVORC-UHFFFAOYSA-N N-ethyl-N-methylamine Natural products CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 1
- 241001556089 Nilaparvata lugens Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000346285 Ostrinia furnacalis Species 0.000 description 1
- 241000437063 Phyllotreta striolata Species 0.000 description 1
- 241000907661 Pieris rapae Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 241000596535 Pseudococcus comstocki Species 0.000 description 1
- 241000866500 Reticulitermes speratus Species 0.000 description 1
- 241000073849 Scotinophara lurida Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000254154 Sitophilus zeamais Species 0.000 description 1
- 241000985245 Spodoptera litura Species 0.000 description 1
- 241000283614 Stephanitis nashi Species 0.000 description 1
- 241000018135 Trialeurodes Species 0.000 description 1
- 241001630065 Unaspis yanonensis Species 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000021329 brown rice Nutrition 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- XKMYKQWJJZRCJV-UHFFFAOYSA-N n,n-bis(chloromethyl)ethanamine Chemical compound CCN(CCl)CCl XKMYKQWJJZRCJV-UHFFFAOYSA-N 0.000 description 1
- JAFGEVXWYLPKGG-UHFFFAOYSA-N n,n-bis(chloromethyl)propan-1-amine Chemical compound CCCN(CCl)CCl JAFGEVXWYLPKGG-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Definitions
- the present invention relates to hexahydrotriazine compounds, a process for preparing the same and insecticides containing the same as active ingredients.
- the hexahydrotriazine compounds provided by this invention are represented by the following general formula (I):
- R stands for lower alkyl or lower alkenyl
- R 1 stands for hydrogen, lower alkyl, lower alkenyl, lower alkynyl or a group indicated by
- R 2 stands for a group indicated by
- a variety of chemicals have been developed and used as insecticides for controlling harmful insects.
- Representative examples of such chemicals are organic phosphorous compounds, carbamate compounds and synthetic pyrethroids.
- many harmful insects have acquired resistance to these chemicals, thus making it difficult to control such insects.
- some conventional insecticides have high insecticidal activity, they might cause environmental pollution problems either due to their high toxicity to warm-blooded animals or fishes and Crustacea or due to their remaining in the environment in large amounts for a long time after use, thus putting the ecological system out of order.
- An object of this invention is to provide novel compounds which (1) more effectively control harmful insects that have acquired resistance to conventional chemicals, (2) are low in toxicity not only to warm-blooded animals but also fishes and Crustacea and (3) remain in decreased amounts in plants and soils after their use. Lastly, such novel compounds do not produce phytotoxicity in various plants.
- Another object of this invention is to provide a process for preparing such compounds.
- a further object of this invention is to provide improved insecticides which (1) more effectively control harmful insects having resistance to conventional insecticides, (2) are low in toxicity not only to warm-blooded animals but also fishes and Crustacea, and (3) remain in decreased amounts in plants and soils after their use. Lastly, such improved insecticides do not produce phytotoxicity in various plants.
- R stands for lower alkyl or lower alkenyl
- R 1 stands for hydrogen, lower alkyl, lower alkenyl, lower alkynyl or a group indicated by
- R 2 stands for a group indicated by
- [0013] can be used as extremely powerful insecticides which exhibit rapid effects.
- the present invention has been developed on the basis of this finding.
- the compounds of this invention represented by the general formula (I) are novel compounds which have not been described in any prior publication and were synthesized by us for the first time. These compounds may be prepared by the processes described below.
- R stands for lower alkyl or lower alkenyl
- R 1 stands for hydrogen, lower alkyl, lower alkenyl, lower-alkynyl or a group indicated by
- R 2 stands for a group indicated by
- the compounds of this invention may be readily prepared by reacting, in a solvent, a compound represented by the general formula (II); with a compound represented by the general formula (III), such as bis(chloromethyl)methylamine, bis(chloromethyl)ethylamine and bis(chloromethyl)propylamine, in the presence of a basic material.
- a compound represented by the general formula (II) such as bis(chloromethyl)methylamine, bis(chloromethyl)ethylamine and bis(chloromethyl)propylamine
- Suitable solvents which may be used in this reaction are; ethers such as diethyl ether and tetrahydrofuran; acetonitrile; aromatic hydrocarbons; chlorinated hydrocarbons; DMF; and DMSO. These solvents may be used alone or in combination.
- Compounds which may be used as the basic materials are, for example, inorganic bases such as sodium hydroxide and potassium carbonate, and organic bases such as pyridine and triethylamine. These bases may be used in excess and particularly, 2.1 to 4 mols per 1 mol of the compound (II) are preferable.
- the reaction temperature may be freely set within a range of from ⁇ 20° C. to 100° C., preferably from ⁇ 5° C. to 10° C.
- R, R 1 and R 2 have the same meanings defined above.
- the compounds of this invention may be readily prepared by reacting a compound represented by the general formula (II) with a primary amine, represented by the general formula R—NH 2 (IV) wherein R has the same meaning defined above, such as methyl amine, ethyl amine and allyl amine and a 37% formalin solution or paraformaldehyde, in a solvent.
- a primary amine represented by the general formula R—NH 2 (IV) wherein R has the same meaning defined above, such as methyl amine, ethyl amine and allyl amine and a 37% formalin solution or paraformaldehyde
- Examples of the suitable solvents which may be used in this reaction are: alcohols such as methanol and ethanol; ethers such as dioxane and tetrahydrofuran; and water. These solvents may be used alone or in combination.
- the reaction temperature may be freely set within a range from a room temperature to a boiling temperature of a solvent used, preferably from 50° C. to 100° C.
- R, R 1 and R 2 have the same meanings defined above and Y stands for halogen or a group indicated by —OSO 2 CH 3 or
- the compounds of this invention may be readily prepared by reacting a compound represented by the general formula (V) with a compound represented by the general formula (VI) in the presence of a basic material in an inert solvent.
- Examples of the suitable solvents which may be used in this reaction are: DMF; DMSO; acetonitrile; and ethers, such as tetrahydrofuran and dioxane. These solvents may be used alone or in combination.
- Compounds which may be used as the basic materials are for example, sodium hydride, potassium carbonate, sodium hydroxide etc. 1.1 to 2.5 mols of these bases per 1 mol of the compound (V) are preferably used.
- the reaction temperature may be freely set within a range from a room temperature to 150° C., preferably from 40° C. to 100° C.
- Hexahydrotriazine compounds of this invention are novel compounds. Typical compounds of this invention are set forth in the following Table 1. TABLE 1 Compound No. R 2 R 1 R Melting Point 1 H CH 3 150 ⁇ 154° C. 2 ′′ ′′ C 2 H 5 124 ⁇ 125° C. 3 ′′ ′′ iC 3 H 2 121 ⁇ 122° C. 4 ′′ ′′ —CH 2 CH ⁇ CH 2 108 ⁇ 109° C. 5 ′′ CH 3 CH 3 116 ⁇ 117° C. 6 ′′ ′′ 125 ⁇ 126° C. 7 C 2 H 5 ′′ 163 ⁇ 164° C. 8 ′′ nC 3 H 2 ′′ 102 ⁇ 104° C.
- An effective amount of any of the compounds of this invention may be applied directly as an insecticide or may be formulated by conventional technology in the form of an emulsion, a wettable powder, a dust, a granule or in a flowable form, and then applied as a formulated product.
- a liquid or solid carrier may be used for preparing a formulated product containing one or more of the compounds of this invention.
- Liquid carriers which may be used for this purpose include, for example, organic solvents, and conveniently used are xylene, chlorobenzene, methylnaphthalene, cyclohexanone, isophorone, alcohols, dimethylformamide and N-methylpyrrolidone.
- solid carriers examples include kaoline, talc, bentonite, diatomaceous earth and clay, and synthetic compounds such as alumina, zeolite and silicates may also be used.
- various adjuvants such as emulsifiers, dispersants, spreaders, wetting agents and penetrating agents, may be used for providing the products with the desired properties of emulsification, dispersion, suspension and penetration.
- the compounds of this invention which are represented by the general formula (I) set forth above, have strong insecticidal activity against various harmful insects, including Hemiptera, Lepidoptera, Coleoptera, Diptera, Orthoptera and Isoptera, and yet are low in toxicity to human beings and animals and do not produce phytotoxicity in various plants, and thus can be practically used as superior insecticides.
- Hemiptera such as Nilaparvata lugens, Laodelphax striatellus, Nephotettix cincticeps, Pseudococcus comstocki, Unaspis yanonensis, Myzus persicae, Aphis gossypii, Lipaphis erysimi, Stephanitis nashi, Scotinophara lurida and Trialeurodes vaporariorus; Lepidoptera such as Pieris rapae, Spodoptera litura, Mamestra brassicae, Chilo suppressalis, Plutera xylostella, Adoxophyes orana, Agrotis segetum, Cnaphalocrocis medinalis and Ostrinia furnacalis ; Coleoptera such as Henosepilachna vigintioctopunctata, Aulacophora femoralis, Phyllotreta striolat
- the compounds of this invention are extremely active for controlling various harmful insects and yet are low in toxicity to warm-blooded animals, fishes and Crustacea, the remaining quantity thereof after their use is small, and they do not produce phytotoxicity in various plants.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
with a di(monohalomethyl)amine compound or a primary amine compound in combination with formalin or paraformaldehyde, or by reacting a hexahydrotriazine derivative with a compound of the formula: R2CH2—Y—.
Description
- 1. Field of the Invention
-
-
-
- 2. Prior Art
- A variety of chemicals have been developed and used as insecticides for controlling harmful insects. Representative examples of such chemicals are organic phosphorous compounds, carbamate compounds and synthetic pyrethroids. However, by the repeated use of these insecticides, many harmful insects have acquired resistance to these chemicals, thus making it difficult to control such insects. On the other hand, although some conventional insecticides have high insecticidal activity, they might cause environmental pollution problems either due to their high toxicity to warm-blooded animals or fishes and Crustacea or due to their remaining in the environment in large amounts for a long time after use, thus putting the ecological system out of order. Accordingly, there is a demand for the development of novel insecticides which more effectively control harmful insects, which have acquired resistance to conventional chemicals, and yet are low in toxicity not only to warm-blooded animals but also fishes and Crustacea. There is also a demand for novel insecticides which remain in plants and soils in decreased amounts after their use, and do not produce phytotoxicity in various plants.
- An object of this invention is to provide novel compounds which (1) more effectively control harmful insects that have acquired resistance to conventional chemicals, (2) are low in toxicity not only to warm-blooded animals but also fishes and Crustacea and (3) remain in decreased amounts in plants and soils after their use. Lastly, such novel compounds do not produce phytotoxicity in various plants.
- Another object of this invention is to provide a process for preparing such compounds.
- A further object of this invention is to provide improved insecticides which (1) more effectively control harmful insects having resistance to conventional insecticides, (2) are low in toxicity not only to warm-blooded animals but also fishes and Crustacea, and (3) remain in decreased amounts in plants and soils after their use. Lastly, such improved insecticides do not produce phytotoxicity in various plants.
-
-
-
- can be used as extremely powerful insecticides which exhibit rapid effects. The present invention has been developed on the basis of this finding.
- Further objects, features and advantages of the present invention will become aparent from the Detailed Description of the Preferred Embodiments which follows, when considered together with the illustrative examples.
-
-
-
- and X stands for halogen.
- In the preparation process (a), as indicated by the reaction formula set forth above, the compounds of this invention may be readily prepared by reacting, in a solvent, a compound represented by the general formula (II); with a compound represented by the general formula (III), such as bis(chloromethyl)methylamine, bis(chloromethyl)ethylamine and bis(chloromethyl)propylamine, in the presence of a basic material.
- Examples of the suitable solvents which may be used in this reaction are; ethers such as diethyl ether and tetrahydrofuran; acetonitrile; aromatic hydrocarbons; chlorinated hydrocarbons; DMF; and DMSO. These solvents may be used alone or in combination. Compounds which may be used as the basic materials are, for example, inorganic bases such as sodium hydroxide and potassium carbonate, and organic bases such as pyridine and triethylamine. These bases may be used in excess and particularly, 2.1 to 4 mols per 1 mol of the compound (II) are preferable.
-
- wherein R, R1 and R2 have the same meanings defined above.
- In the preparation process (b) as indicated by the reaction formula set forth above, the compounds of this invention may be readily prepared by reacting a compound represented by the general formula (II) with a primary amine, represented by the general formula R—NH2 (IV) wherein R has the same meaning defined above, such as methyl amine, ethyl amine and allyl amine and a 37% formalin solution or paraformaldehyde, in a solvent.
- Examples of the suitable solvents which may be used in this reaction are: alcohols such as methanol and ethanol; ethers such as dioxane and tetrahydrofuran; and water. These solvents may be used alone or in combination. The reaction temperature may be freely set within a range from a room temperature to a boiling temperature of a solvent used, preferably from 50° C. to 100° C.
-
- In the preparation process (c), as indicated by the reaction formula set forth above, the compounds of this invention may be readily prepared by reacting a compound represented by the general formula (V) with a compound represented by the general formula (VI) in the presence of a basic material in an inert solvent.
- Examples of the suitable solvents which may be used in this reaction are: DMF; DMSO; acetonitrile; and ethers, such as tetrahydrofuran and dioxane. These solvents may be used alone or in combination. Compounds which may be used as the basic materials are for example, sodium hydride, potassium carbonate, sodium hydroxide etc. 1.1 to 2.5 mols of these bases per 1 mol of the compound (V) are preferably used. The reaction temperature may be freely set within a range from a room temperature to 150° C., preferably from 40° C. to 100° C.
- Hexahydrotriazine compounds of this invention are novel compounds. Typical compounds of this invention are set forth in the following Table 1.
TABLE 1 Compound No. R2 R1 R Melting Point 1 H CH3 150˜154° C. 2 ″ ″ C2H5 124˜125° C. 3 ″ ″ iC3H2 121˜122° C. 4 ″ ″ —CH2CH═CH2 108˜109° C. 5 ″ CH3 CH3 116˜117° C. 6 ″ ″ 125˜126° C. 7 C2H5 ″ 163˜164° C. 8 ″ nC3H2 ″ 102˜104° C. 9 nC3H7 CH3 139˜143° C. 10 —CH2CH═CH2 ″ 112˜114° C. 11 ″ —CH2C≡CH ″ 124˜125° C. 12 ″ ″ 188˜189° C. (decomp.) - An effective amount of any of the compounds of this invention may be applied directly as an insecticide or may be formulated by conventional technology in the form of an emulsion, a wettable powder, a dust, a granule or in a flowable form, and then applied as a formulated product. A liquid or solid carrier may be used for preparing a formulated product containing one or more of the compounds of this invention. Liquid carriers which may be used for this purpose include, for example, organic solvents, and conveniently used are xylene, chlorobenzene, methylnaphthalene, cyclohexanone, isophorone, alcohols, dimethylformamide and N-methylpyrrolidone. Examples of solid carriers include kaoline, talc, bentonite, diatomaceous earth and clay, and synthetic compounds such as alumina, zeolite and silicates may also be used. In preparation of the formulated products, various adjuvants, such as emulsifiers, dispersants, spreaders, wetting agents and penetrating agents, may be used for providing the products with the desired properties of emulsification, dispersion, suspension and penetration.
- The compounds of this invention, which are represented by the general formula (I) set forth above, have strong insecticidal activity against various harmful insects, including Hemiptera, Lepidoptera, Coleoptera, Diptera, Orthoptera and Isoptera, and yet are low in toxicity to human beings and animals and do not produce phytotoxicity in various plants, and thus can be practically used as superior insecticides.
- Examples of harmful insects which may be effectively controlled by the compounds of this invention are as follows:
- Hemiptera such asNilaparvata lugens, Laodelphax striatellus, Nephotettix cincticeps, Pseudococcus comstocki, Unaspis yanonensis, Myzus persicae, Aphis gossypii, Lipaphis erysimi, Stephanitis nashi, Scotinophara lurida and Trialeurodes vaporariorus; Lepidoptera such as Pieris rapae, Spodoptera litura, Mamestra brassicae, Chilo suppressalis, Plutera xylostella, Adoxophyes orana, Agrotis segetum, Cnaphalocrocis medinalis and Ostrinia furnacalis; Coleoptera such as Henosepilachna vigintioctopunctata, Aulacophora femoralis, Phyllotreta striolata, Lissorhoptrus oryzophilus, Sitophilus zeamais and Anomala rufocuprea; Diptera such as Musca domestica, Hylemia platura, Culex pipiens; Orthoptera such as Gryllotalpa africana, Blatella germanica and Locusta migratoria; and Isoptera such as Coptotermes formosanus and Reticulitermes speratus.
- The present invention will now further be explained by way of the following non-limiting examples.
- The processes for the preparation of the compounds of this invention are described in detail in the following Synthesis Examples.
- 0.6 g of 1-(2-chloro-5-pyridylmethyl)-3-nitroguanidine and 0.4 g of bis(chloromethyl)methylamine were suspended in dried THF. To the suspension, a solution of 0.52 g of triethylamine in THF was added dropwise with cooling. The reaction mixture was stirred for 1 hour, and then poured into ice water. The mixture was extracted with dichloromethane. After the extract was dried over anhydrous magnesium sulfate, dichloromethane was distilled off. The residue was recrystallized from methanol to obtain 0.78 g of the title compound. This compound is No. 1 in Table 1. m.p.: 150-154° C.
- To a stirring mixture of 1 g of 1-(2-chloro-5-pyridylmethyl)-3-nitroguanidine, 0.28 g of 70% ethylamine in water and 20 ml of ethanol, 0.71 g of 37% formalin solution was added dropwise with heating. The reaction mixture was heated under reflux for two hours. After being allowed to cool to room temperature, the crystals formed, which were filtrated off and recrystallized from methanol to obtain 1.15 g of the title compound. This compound is No. 2 in Table 1. m.p.: 124-125° C.
- 1 g of 1,5-dimethyl-2-nitroiminohexahydro-1,3,5-triazine was dissolved in 20 ml of dried DMF. To the solution, 0.27 g of 60% sodium hydride was added with cooling. The mixture was stirred for 1 hour at room temperature until evolution of hydrogen was ceased and then the mixture was heated with stirring further for 1 hour at 50° C. To the mixture, a solution of 0.9 g of 2-chloro-5-pyridylmethylchloride in 8 ml of dried DMF was added dropwise at 40-50° C. After this addition, the reaction mixture was heated with stirring it for two hours at 70-80° C. The mixture was poured into ice-water and extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate, and dichloromethane was distilled off. The residue was purified by a column chromatography to obtain 1.3 g of the title compound. This compound is No.5 in Table 1. m.p.: 116-117° C.
- 1.7 g of 1,5-dimethyl-2-nitroiminohexahydro-1,3,5-triazine was dissolved in 20 ml of dried DMF. To the solution, 0.28 g of 60% sodium hydride was added portionwise with cooling. The mixture was stirred for 1 hour at room temperature until evolution of hydrogen was ceased and then the mixture was heated with stirring further for 1 hour at 50° C. To the mixture, a solution of 1.7 g of 2-chloro-5-thiazolylmethylchloride in 8 ml of dried DMF was added dropwise at 40-50° C. After this addition, the reaction mixture was heated with stirring for two hours at 70-80° C. The mixture was poured into ice-water and extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate, and dichloromethane was distilled off. The residue was purified by a column chromatography to obtain 0.82 g of the title compound. This compound is No.6 in Table 1. m.p.: 125-126° C.
- Some specific Formulation Examples are shown below. However, it is noted that the carriers, surfactants and other additives which may be used in formulation of the insecticides according to this invention are not limited by the following Formulation Examples. In the following Formulation Examples, “part” stands for “part by weight”.
- 32.5 Parts of the Compound No.1 in Table 1, 3 parts of lignin sulfonic acid, 4 parts of polyoxyethylene alkylphenyl ether, 2 parts of silicon dioxide hydrate and 58.5 parts of clay are well mixed while being powdered to obtain a wettable powder.
- 5.4 Parts of the Compound No. 2 in Table 1, 2 parts of silicon dioxide hydrate and 92.6 parts of talc are well mixed while being powdered to obtain a dust.
- 5.4 Parts of the Compound No. 3 in Table 1, 3 parts of lignin sulfonate, 1 part of sodium dodecylbenzenesulfonate, 30 parts of bentonite and 60.6 parts of clay are well mixed while being powdered. The mixture is then kneaded with water, granulated and dried to obtain granules.
- The insecticidal effects of the compounds of this invention are shown by referring to some Test Examples.
- Five rice seedlings having a height of about 7 cm were dipped, for 10 seconds, into aqueous dilutions of wettable powder each containing a predetermined concentration of each sample compound, prepared in accordance with the procedure as described in Formulation Example 1. After air drying, the roots of the five rice seedlings were wrapped with sanitary cotton dampened with water, and placed in a glass cylinder having a diameter of 3 cm and a height of 20 cm. Ten second instar larvae of a green rice leafhopper which had acquired resistance to chemicals were released into each glass cylinder. The cylinder was allowed to stand in a room maintained at 26° C. The mortality of the larvae was examined 48 hours after treatment. The results are shown in Table 2.
TABLE 2 Compound No. Mortality (%), 500 ppm 1 100 2 100 3 100 4 100 5 100 6 100 7 100 8 100 9 100 10 100 11 100 12 100 Comparative 70 Compound -
- Five rice seedlings having a height of about 7 cm were dipped, for 10 seconds, into aqueous dilutions of wettable powder each containing a predetermined concentration of each sample compound, prepared in accordance with the procedure as described in Formulation Example 1. After air drying, the roots of the five rice seedlings were wrapped with sanitary cotton dampened with water, and placed in a glass cylinder having a diameter of 3 cm and a height of 20 cm. Ten second instar larvae of a brown rice planthopper which had acquired resistance to chemicals were released into each glass cylinder. The cylinder was allowed to stand in a room maintained at 26° C. The mortality of the larvae was examined 48 hours after treatment. The results are shown in Table 3.
TABLE 3 Compound No. Mortality (%), 500 ppm 1 100 2 100 3 100 4 100 5 100 6 100 7 100 8 100 9 100 10 100 11 100 12 100 Comparative 65 Compound - Note: The comparative compound set forth in Table 3 is the same as that in Table 2.
- As will be apparent from the foregoing, the compounds of this invention are extremely active for controlling various harmful insects and yet are low in toxicity to warm-blooded animals, fishes and Crustacea, the remaining quantity thereof after their use is small, and they do not produce phytotoxicity in various plants.
Claims (29)
2. The hexahydrotriazine compound according to which is 1-(2-chloro-5-pyridylmethyl)-5-methyl-2-nitroiminohexahydro-1,3,5-triazine.
claim 1
3. The hexahydrotriazine compound according to which is 1-(2-chloro-5-pyridylmethyl)-5-ethyl-2-nitroiminohexahydro-1,3,5-triazine.
claim 1
4. The hexahydrotriazine compound according to which is 1-(2-chloro-5-pyridylmethyl)-5-isopropyl-2-nitroiminohexahydro-1,3,5-triazine.
claim 1
5. The hexahydrotriazine compound according to which is 1-( 2-chloro-5-pyridylmethyl )-5-allyl-2-nitroiminohexahydro-1,3,5-triazine.
claim 1
6. The hexahydrotriazine compound according to which is 1-(2-chloro-5-pyridylmethyl )-3,5-dimethyl-2-nitroiminohexahydro-1,3,5-triazine.
claim 1
7. The hexahydrotriazine compound according to which is 1-(2-chloro-5-thiazolylmethyl)-3,5-dimethyl-2-nitroiminohexahydro-1,3,5-triazine.
claim 1
8. The hexahydrotriazine compound according to which is 1-(2-chloro-5-pyridylmethyl)-3-ethyl-5-methyl-2-nitroiminohexahydro-1,3,5-triazine.
claim 1
9. The hexahydrotriazine compound according to which is 1-(2-chloro-5-pyridylmethyl)-3-propyl-5-methyl-2-nitroiminohexahydro-1,3,5-triazine.
claim 1
10. The hexahydrotriazine compound according to which is 1-(2-chloro-5-thiazolylmethyl)-3-propyl-5-methyl-2-nitroiminohexahydro-1,3,5-triazine.
claim 1
11. The hexahydrotriazine compound according to which is 1-(2-chloro-5-pyridylmethyl)-3-allyl-5-methyl-2-nitroiminohexahydro-1,3,5-triazine.
claim 1
12. The hexahydrotriazine compound according to which is 1-(2-chloro-5-pyridylmethyl)-3-propargyl-5-methyl-2-nitroiminohexahydro-1,3,5-triazine.
claim 1
13. The hexahydrotriazine compound according to which is 1,3-bis(2-chloro-5-pyridylmethyl)-2-nitroiminohexahydro-1,3,5-triazine.
claim 1
14. A process for preparing a hexahydrotriazine compound represented by the following general formula (I):
wherein R stands for lower alkyl or lower alkenyl; R1 stands for hydrogen, lower alkyl, lower alkenyl, lower alkynyl or a group indicated by
and R2 Stands for a group indicated by
or
comprising the step of reacting a compound represented by the general formula (II):
wherein R1 and R2 have the same meanings defined above, with a compound represented by the general formula (III)
R—N(CH2X)2 (III)
wherein R has the same meaning defined above and X stands for halogen.
15. A process for preparing a hexahydrotriazine compound represented by the following general formula (I):
wherein R stands for lower alkyl or lower alkenyl; R1 stands for hydrogen, lower alkyl, lower alkenyl, lower alkynyl or a group indicated by
and R2 stands for a group indicated by
or
comprising the step of reacting a compound represented by the general formula (II):
wherein R1 and R2 have the same meanings defined above, with a primary amine represented by the general formula (IV):
R—NH2
wherein R has the same meaning defined above, and formalin or paraformaldehyde.
16. A process for preparing a hexahydrotriazine compound represented by the following general formula (I):
wherein R stands for lower alkyl or lower alkenyl; R1 stands for hydrogen, lower alkyl, lower alkenyl, lower alkynyl or a group indicated by
and R2 stands for a group indicated by
or
comprising the step of reacting a compound represented by the general formula (V):
wherein R and R1 have the same meanings defined above, with a compound represented by the general formula (VI):
R2CH2—Y (VI)
wherein R2 has the same meaning defined above and Y stands for halogen or a group indicated by —OSO2CH3 or
17. An insecticide containing a suitable carrier, and, as an active ingredient, a hexahydrotriazine compound represented by the following general formula (I):
wherein R stands for lower alkyl or lower alkenyl; R1 stands for hydrogen, lower alkyl, lower alkenyl, lower alkynyl or a group indicated by
and R2 stands for a group indicated by
18. The insecticide according to wherein the compound is 1-(2-chloro-5-pyridylmethyl)-5-methyl-2-nitroiminohexahydro-1,3,5-triazine.
claim 17
19. The insecticide according to wherein the compound is 1-(2-chloro-5-pyridylmethyl)-5-ethyl-2-nitroiminohexahydro-1,3,5-triazine.
claim 17
20. The insecticide according to wherein the compound is 1-(2-chloro-5-pyridylmethyl)-5-isopropyl-2-nitroiminohexahydro-1,3,5-triazine.
claim 17
21. The insecticide according to wherein the compound is 1-(2-chloro-5-pyridylmethyl)-5-allyl-2-nitroiminohexahydro-1,3,5-triazine.
claim 17
22. The insecticide according to wherein the compound is 1-(2-chloro-5-pyridylmethyl)-3,5-dimethyl-2-nitroiminohexahydro-1,3,5-triazine.
claim 17
23. The insecticide according to wherein the compound is 1-(2-chloro-5-thiazolylmethyl)-3,5-dimethyl-2-nitroiminohexahydro-1,3,5-triazine.
claim 17
24. The insecticide according to wherein the compound is 1-(2-chloro-5-pyridylmethyl)-3-ethyl-5-methyl-2-nitroiminohexahydro-1,3,5-triazine.
claim 17
25. The insecticide according to wherein the compound is 1-(2-chloro-5-pyridylmethyl )-3-propyl-5-methyl-2-nitroiminohexahydro-1,3,5-triazine.
claim 17
26. The insecticide according to wherein the compound is 1-(2-chloro-5-thiazolylmethyl)-3-propyl-5-methyl-2-nitroiminohexahydro-1,3,5-triazine.
claim 17
27. The insecticide according to wherein the compound is 1-(2-chloro-5-pyridylmethyl)-3-allyl-5-methyl-2-nitroiminohexahydro-1,3,5-triazine.
claim 17
28. The insecticide according to wherein the compound is 1-(2-chloro-5-pyridylmethyl)-3-propargyl-5-methyl-2-nitroiminohexahydro-1,3,5-triazine.
claim 17
29. The insecticide according to wherein the compound is 1,3-bis(2-chloro-5-pyridylmethyl)-2-nitroiminohexahydro-1,3,5-triazine.
claim 17
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/729,865 US20010046994A1 (en) | 1989-11-10 | 2000-12-06 | Hexahydrotriazine compounds and insecticides |
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP292675/1989 | 1989-11-10 | ||
JP29267589 | 1989-11-10 | ||
JP2024199A JPH06776B2 (en) | 1989-11-10 | 1990-02-02 | Hexahydrotriazine compound, its production method and insecticide |
US07/606,848 US6187773B1 (en) | 1989-11-10 | 1990-10-31 | Hexahydrotriazine compounds and insecticides |
US09/729,865 US20010046994A1 (en) | 1989-11-10 | 2000-12-06 | Hexahydrotriazine compounds and insecticides |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US07/606,848 Division US6187773B1 (en) | 1989-11-10 | 1990-10-31 | Hexahydrotriazine compounds and insecticides |
Publications (1)
Publication Number | Publication Date |
---|---|
US20010046994A1 true US20010046994A1 (en) | 2001-11-29 |
Family
ID=26361680
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US07/606,848 Expired - Fee Related US6187773B1 (en) | 1989-11-10 | 1990-10-31 | Hexahydrotriazine compounds and insecticides |
US09/729,865 Abandoned US20010046994A1 (en) | 1989-11-10 | 2000-12-06 | Hexahydrotriazine compounds and insecticides |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US07/606,848 Expired - Fee Related US6187773B1 (en) | 1989-11-10 | 1990-10-31 | Hexahydrotriazine compounds and insecticides |
Country Status (5)
Country | Link |
---|---|
US (2) | US6187773B1 (en) |
EP (1) | EP0428941B1 (en) |
CN (2) | CN1026648C (en) |
AU (1) | AU628229B2 (en) |
DE (1) | DE69019107T2 (en) |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6528651B1 (en) | 1999-12-21 | 2003-03-04 | Bayer Aktiengesellschaft | Method for production of 1,3-disubtituted 2-nitroguanidines |
US6716874B1 (en) | 1999-03-24 | 2004-04-06 | Bayer Aktiengesellschaft | Synergistic insecticide mixtures |
US20040167177A1 (en) * | 2001-05-03 | 2004-08-26 | Jorn Stolting | Method for producing 1,3-disubstituted 2-nitroguanidines |
US20050014646A1 (en) * | 2003-07-18 | 2005-01-20 | Schwarz Michael R. | Method of minimizing herbicidal injury |
US6893651B1 (en) | 1999-10-07 | 2005-05-17 | Bayer Aktiengesellschaft | Active ingredient combinations having insecticidal and acaricidal properties |
US20070157507A1 (en) * | 2004-08-25 | 2007-07-12 | Reid Byron L | Method of controlling termites |
US20100311580A1 (en) * | 2007-12-11 | 2010-12-09 | Bayer Cropscience Ag | Active Compound Combinations |
WO2015195378A1 (en) * | 2014-06-16 | 2015-12-23 | International Business Machines Corporation | Methods and apparatus for controlling metals in liquids |
US9599560B2 (en) | 2014-06-06 | 2017-03-21 | International Business Machines Corporation | Methods and apparatus for detecting metals in liquids |
US9919979B2 (en) | 2005-01-21 | 2018-03-20 | Bayer Cropscience Lp | Fertilizer-compatible composition |
Families Citing this family (392)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2610988B2 (en) | 1989-03-09 | 1997-05-14 | 日本バイエルアグロケム 株式会社 | New heterocyclic compounds and insecticides |
US6232309B1 (en) | 1989-03-09 | 2001-05-15 | Nihon Bayer Agrochem K.K. | Insecticidal heterocyclic compounds |
IL99576A0 (en) * | 1990-10-05 | 1992-08-18 | Ciba Geigy Ag | Triazacyclohexane derivatives |
TW198724B (en) * | 1990-10-24 | 1993-01-21 | Ciba Geigy Ag | |
DE4232561A1 (en) * | 1992-09-29 | 1994-03-31 | Bayer Ag | Fighting fish parasites |
DE69412546T2 (en) * | 1993-06-04 | 1998-12-24 | Bayer Agrochem Kk | Means for preserving technical materials against insects |
DE4414569A1 (en) * | 1994-04-27 | 1995-11-02 | Bayer Ag | Use of substituted amines for the treatment of brain disorders |
DE4417742A1 (en) | 1994-05-20 | 1995-11-23 | Bayer Ag | Non-systemic control of parasites |
DE4426753A1 (en) | 1994-07-28 | 1996-02-01 | Bayer Ag | Means for controlling plant pests |
JP3493476B2 (en) * | 1994-09-30 | 2004-02-03 | バイエルクロップサイエンス株式会社 | Termite control composition |
DE19548872A1 (en) | 1995-12-27 | 1997-07-03 | Bayer Ag | Synergistic insecticidal mixtures |
US6828275B2 (en) | 1998-06-23 | 2004-12-07 | Bayer Aktiengesellschaft | Synergistic insecticide mixtures |
DE19622355A1 (en) | 1996-06-04 | 1997-12-11 | Bayer Ag | Molded bodies that release agrochemicals |
DE19712411A1 (en) | 1997-03-25 | 1998-10-01 | Bayer Ag | Process for the preparation of 1,3-disubstituted 2-nitroguanidines |
DE19712885A1 (en) * | 1997-03-27 | 1998-10-01 | Bayer Ag | Process for the preparation of N-alkyl-N'-nitroguanidines |
US6118007A (en) * | 1997-03-31 | 2000-09-12 | Mitsui Chemicals, Inc. | Preparation process of nitroguanidine derivatives |
JP2001515066A (en) * | 1997-08-20 | 2001-09-18 | ノバルティス アクチエンゲゼルシャフト | Method for producing substituted 2-nitroguanidine derivative |
ZA9711701B (en) * | 1997-12-30 | 1998-09-30 | Bayer Ag | Termite control |
ZA9711700B (en) * | 1997-12-30 | 1998-08-26 | Bayer Ag | Locust control. |
DE19807630A1 (en) | 1998-02-23 | 1999-08-26 | Bayer Ag | Water-based composition useful for controlling parasitic insects and mites, especially lice, on humans |
DE19807633A1 (en) * | 1998-02-23 | 1999-08-26 | Bayer Ag | Storage-stable water-based composition for controlling parasitic insects, especially fleas, on animals, e.g. livestock and pets |
JP4196427B2 (en) | 1998-04-09 | 2008-12-17 | 住友化学株式会社 | Harmful arthropod control composition |
DE19823396A1 (en) * | 1998-05-26 | 1999-12-02 | Bayer Ag | Synergistic insecticidal mixtures |
JP4538863B2 (en) * | 1998-06-08 | 2010-09-08 | 住友化学株式会社 | How to get rid of parasites |
US6140350A (en) * | 1998-06-08 | 2000-10-31 | Sumitomo Chemical Company, Limited | Method for controlling ectoparasites |
US6201017B1 (en) | 1998-07-27 | 2001-03-13 | Sumitomo Chemical Co., Ltd. | Ectoparasite controlling agent for animals |
AU750504B2 (en) * | 1998-07-30 | 2002-07-18 | Sumitomo Chemical Company, Limited | Tick controlling agent |
JP4214594B2 (en) | 1998-09-28 | 2009-01-28 | 住友化学株式会社 | Termite control aerosol |
US6149913A (en) * | 1998-11-16 | 2000-11-21 | Rhone-Poulenc Ag Company, Inc. | Compositions and methods for controlling insects |
DE19900519A1 (en) | 1999-01-08 | 2000-07-13 | Bayer Ag | Substituted guanidine derivatives |
US6156703A (en) * | 1999-05-21 | 2000-12-05 | Ijo Products, Llc | Method of inhibiting fruit set on fruit producing plants using an aqueous emulsion of eicosenyl eicosenoate and docosenyl eicosenoate |
DE10024934A1 (en) * | 2000-05-19 | 2001-11-22 | Bayer Ag | Pesticidal agent contains synergistic mixture of 3-aryl-4-hydroxy-2-oxo-pyrroline derivative and nicotinergic acetylcholine receptor agonist or antagonist |
US20020103233A1 (en) | 2000-11-30 | 2002-08-01 | Arther Robert G. | Compositions for enhanced acaricidal activity |
DE10117676A1 (en) | 2001-04-09 | 2002-10-10 | Bayer Ag | Pesticidal composition, useful for controlling fleas and ticks on animals, contains permethrin and imidacloprid, in N-methylpyrrolidone |
DE102004006075A1 (en) | 2003-11-14 | 2005-06-16 | Bayer Cropscience Ag | Composition for controlling animal pests comprises a synergistic combination of a nicotinergic acetylcholine receptor agonist or antagonist and an anthranilamide derivative |
DE102007045922A1 (en) | 2007-09-26 | 2009-04-02 | Bayer Cropscience Ag | Drug combinations with insecticidal and acaricidal properties |
DE102007045956A1 (en) | 2007-09-26 | 2009-04-09 | Bayer Cropscience Ag | Combination of active ingredients with insecticidal and acaricidal properties |
EP2070416A1 (en) | 2007-12-11 | 2009-06-17 | Bayer CropScience AG | Use of substance combinations for combating animal pests |
EP2070411A1 (en) | 2007-12-11 | 2009-06-17 | Bayer CropScience AG | Active compound combinations |
EP2070415A1 (en) | 2007-12-11 | 2009-06-17 | Bayer CropScience AG | Active compound combinations |
EP2070413A1 (en) | 2007-12-11 | 2009-06-17 | Bayer CropScience AG | Active compound combinations |
EP2227951A1 (en) | 2009-01-23 | 2010-09-15 | Bayer CropScience AG | Application of enaminocarbonyl compounds for combating viruses transmitted by insects |
WO2010103065A1 (en) | 2009-03-11 | 2010-09-16 | Basf Se | Fungicidal compositions and their use |
EP2413691A2 (en) | 2009-04-02 | 2012-02-08 | Basf Se | Method for reducing sunburn damage in plants |
EP2440535A1 (en) | 2009-06-12 | 2012-04-18 | Basf Se | Antifungal 1,2,4-triazolyl derivatives having a 5- sulfur substituent |
WO2010146032A2 (en) | 2009-06-16 | 2010-12-23 | Basf Se | Fungicidal mixtures |
EP2443097A1 (en) | 2009-06-18 | 2012-04-25 | Basf Se | Antifungal 1, 2, 4-triazolyl derivatives |
MX2011012903A (en) | 2009-06-18 | 2012-02-01 | Basf Se | Fungicidal mixtures. |
WO2010146116A1 (en) | 2009-06-18 | 2010-12-23 | Basf Se | Triazole compounds carrying a sulfur substituent |
US20120088663A1 (en) | 2009-06-18 | 2012-04-12 | Basf Se | Triazole Compounds Carrying a Sulfur Substituent |
WO2010146115A1 (en) | 2009-06-18 | 2010-12-23 | Basf Se | Triazole compounds carrying a sulfur substituent |
WO2010146113A1 (en) | 2009-06-18 | 2010-12-23 | Basf Se | Antifungal 1, 2, 4-triazolyl derivatives having a 5- sulfur substituent |
US20120088660A1 (en) | 2009-06-18 | 2012-04-12 | Basf Se | Antifungal 1,2,4-triazolyl Derivatives |
WO2010149758A1 (en) | 2009-06-25 | 2010-12-29 | Basf Se | Antifungal 1, 2, 4-triazolyl derivatives |
BR112012001001A2 (en) | 2009-07-14 | 2016-11-16 | Basf Se | azole compounds of formulas i and ii, compounds of formulas i and i, compounds of formula ix, agricultural composition, use of a pharmaceutical compound, method for treating cancer or virus infections to combat zoopathogenic or humanopathogenic fungi |
BR112012001595B1 (en) | 2009-07-28 | 2018-06-05 | Basf Se | PESTICIDE SUSPOEMULSION COMPOSITION, METHOD FOR PREPARING PESTICIDE SUSPOEMULSION COMPOSITION, USE OF A SUSPOEMULSION COMPOSITION, METHODS FOR COMBATING PHYTOPATHOGENIC FUNGI AND METHOD FOR TREATING SEEDS |
WO2011026796A1 (en) | 2009-09-01 | 2011-03-10 | Basf Se | Synergistic fungicidal mixtures comprising lactylates and method for combating phytopathogenic fungi |
KR101845794B1 (en) | 2009-10-15 | 2018-04-05 | 바이엘 크롭사이언스 악티엔게젤샤프트 | Active compound combinations |
WO2011069912A1 (en) | 2009-12-07 | 2011-06-16 | Basf Se | Triazole compounds, use thereof and agents containing said compounds |
WO2011069916A1 (en) | 2009-12-08 | 2011-06-16 | Basf Se | Triazole compounds, use thereof as a fungicide, and agents comprising same |
WO2011069894A1 (en) | 2009-12-08 | 2011-06-16 | Basf Se | Triazole compounds, use thereof, and agents containing same |
WO2011110583A2 (en) | 2010-03-10 | 2011-09-15 | Basf Se | Fungicidal mixtures comprising triazole derivatives |
EP2366289A1 (en) | 2010-03-18 | 2011-09-21 | Basf Se | Synergistic fungicidal mixtures |
EA022448B1 (en) | 2010-03-18 | 2016-01-29 | Басф Се | Fungicidal compositions comprising a phosphate solubilizing microorganism and a fungicidally active compound |
DE102011017670A1 (en) | 2010-04-29 | 2011-11-03 | Basf Se | Composition, useful e.g. for combating phytopathogenic harmful fungi, e.g. soil-borne pathogens, from classes of Plasmodiophoromycetes, comprises 2',4'-dimethoxy-4-cyclopropyl-1,2,3-thiadiazol-5-carboxanilide and fluxapyroxad |
DE102011017716A1 (en) | 2010-04-29 | 2011-11-03 | Basf Se | Composition, useful e.g. for combating phytopathogenic harmful fungi, e.g. soil-borne pathogens, from classes of Plasmodiophoromycetes, comprises 2',4'-dimethoxy-4-cyclopropyl-1,2,3-thiadiazol-5-carboxanilide and triticonazole |
DE102011017715A1 (en) | 2010-04-29 | 2012-03-08 | Basf Se | Composition useful for controlling phytopathogenic harmful fungi, and protecting plant propagation materials, comprises 2',4'-dimethoxy-4-cyclopropyl-1,2,3-thiadiazol-5-carboxanilide and pyrimethanil as active ingredients |
DE102011017541A1 (en) | 2010-04-29 | 2011-11-10 | Basf Se | Composition useful for controlling phytopathogenic harmful fungi, and protecting a plant propagation material, comprises2',4'-dimethoxy-4-cyclopropyl-1,2,3-thiadiazole-5-carboxanilide and silthiofam |
DE102011017669A1 (en) | 2010-04-29 | 2011-11-03 | Basf Se | Composition, useful e.g. for combating phytopathogenic harmful fungi, e.g. soil-borne pathogens, from classes of Plasmodiophoromycetes, comprises 2',4'-dimethoxy-4-cyclopropyl-1,2,3-thiadiazol-5-carboxanilide and fludioxonil |
EP2402340A1 (en) | 2010-06-29 | 2012-01-04 | Basf Se | Pyrazolopyridine compounds |
EP2402343A1 (en) | 2010-06-29 | 2012-01-04 | Basf Se | Pyrazole-fused bicyclic compounds |
EP2402345A1 (en) | 2010-06-29 | 2012-01-04 | Basf Se | Pyrazole fused bicyclic compounds |
EP2402339A1 (en) | 2010-06-29 | 2012-01-04 | Basf Se | Pyrazolopyridine compounds |
EP2402335A1 (en) | 2010-06-29 | 2012-01-04 | Basf Se | Pyrazolopyridine compounds |
EP2401915A1 (en) | 2010-06-29 | 2012-01-04 | Basf Se | Pyrazolopyridine compounds |
EP2402337A1 (en) | 2010-06-29 | 2012-01-04 | Basf Se | Pyrazolopyridine compounds |
EP2402344A1 (en) | 2010-06-29 | 2012-01-04 | Basf Se | Pyrazole fused bicyclic compounds |
EP2402336A1 (en) | 2010-06-29 | 2012-01-04 | Basf Se | Pyrazolopyridine compounds |
EP2402338A1 (en) | 2010-06-29 | 2012-01-04 | Basf Se | Pyrazolopyridine compounds |
KR20130101003A (en) | 2010-08-03 | 2013-09-12 | 바스프 에스이 | Fungicidal compositions |
EP2447261A1 (en) | 2010-10-29 | 2012-05-02 | Basf Se | Pyrrole, furane and thiophene derivatives and their use as fungicides |
EP2447262A1 (en) | 2010-10-29 | 2012-05-02 | Basf Se | Pyrrole, furane and thiophene derivatives and their use as fungicides |
EP2465350A1 (en) | 2010-12-15 | 2012-06-20 | Basf Se | Pesticidal mixtures |
CN102070629A (en) * | 2010-12-28 | 2011-05-25 | 上海师范大学 | Novel nicotine and clothianidin analogue pesticide and preparation method thereof |
EP2481284A3 (en) | 2011-01-27 | 2012-10-17 | Basf Se | Pesticidal mixtures |
PL2688405T3 (en) | 2011-03-23 | 2018-05-30 | Basf Se | Compositions containing polymeric, ionic compounds comprising imidazolium groups |
WO2012140001A1 (en) | 2011-04-15 | 2012-10-18 | Basf Se | Use of substituted dithiine-dicarboximides for combating phytopathogenic fungi |
CN103476259A (en) | 2011-04-15 | 2013-12-25 | 巴斯夫欧洲公司 | Use of substituted dithiine-tetracarboximides for combating phytopathogenic fungi |
CN103491775A (en) | 2011-04-21 | 2014-01-01 | 巴斯夫欧洲公司 | 3, 4-disubstituted pyrrole 2,5-diones and their use as fungicides |
US20140121103A1 (en) | 2011-06-17 | 2014-05-01 | Basf Se | Compositions comprising fungicidal substituted dithiines and further actives |
CN102432561A (en) * | 2011-07-06 | 2012-05-02 | 山东京蓬生物药业股份有限公司 | Method for preparing neonicotine pesticide clothianidin |
EA026736B1 (en) | 2011-07-13 | 2017-05-31 | Басф Агро Б.В. | Fungicidal substituted 2-[2-halogenalkyl-4-(phenoxy)phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds |
CN103649058A (en) | 2011-07-15 | 2014-03-19 | 巴斯夫欧洲公司 | Fungicidal alkyl- and aryl-substituted 2-[2-chloro-4-(dihalo-phenoxy)-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds |
BR112014000319B1 (en) | 2011-07-15 | 2019-05-14 | Basf Se | USES OF FORMULA I COMPOUNDS, COMPOUNDS, PHYTOPATHOGENIC FUNGI METHODS, FORMULA I COMPOUND PREPARATION PROCESSES AND AGROCHEMICAL COMPOSITION |
WO2013010894A1 (en) | 2011-07-15 | 2013-01-24 | Basf Se | Fungicidal phenylalkyl-substituted 2-[2-chloro-4-(4-chloro-phenoxy)-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds |
JP2014529594A (en) | 2011-08-15 | 2014-11-13 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | Bactericidal substituted 1- {2-cyclyloxy-2- [2-halo-4- (4-halogen-phenoxy) -phenyl] -ethyl} -1H- [1,2,4] triazole compounds |
EP2744790B1 (en) | 2011-08-15 | 2016-04-27 | Basf Se | Fungicidal substituted 1-{2-[2-halo-4-(4-halogen-phenoxy)-phenyl]-2-alkoxy-2-alkynyl/alkenyl-ethyl}-1h-[1,2,4]triazole compounds |
AR087537A1 (en) | 2011-08-15 | 2014-04-03 | Basf Se | FUNGICIDE COMPOUNDS OF 1- {2- [2-HALO-4- (4-HALOGEN-Phenoxy) -Phenyl] -2-ALCOXI-2-CICLIL-ETIL} -1H- [1,2,4] SUBSTITUTED TRIAZOL |
EP2744789A1 (en) | 2011-08-15 | 2014-06-25 | Basf Se | Fungicidal substituted 1-{2-[2-halo-4-(4-halogen-phenoxy)-phenyl]-2-alkoxy-hexyl}-1h [1,2,4]triazole compounds |
BR112014003331A8 (en) | 2011-08-15 | 2019-03-19 | Basf Se | compounds, processes for preparing compounds of formula I, agrochemical compositions and uses of compounds of formula I or viii |
CA2842262A1 (en) | 2011-08-15 | 2013-02-21 | Basf Se | Fungicidal substituted 1-{2-[2-halo-4-(4-halogen-phenoxy)-phenyl]-2-alkoxy-3-methyl-butyl}-1h-[1,2,4]triazole compounds |
KR20140054237A (en) | 2011-08-15 | 2014-05-08 | 바스프 에스이 | Fungicidal substituted 1-{2-[2-halo-4-(4-halogen-phenoxy)-phenyl]-2-alkynyloxy-ethyl}-1h-[1,2,4]triazole compounds |
EP2559688A1 (en) | 2011-08-15 | 2013-02-20 | Basf Se | Fungicidal substituted 1-{2-[2-halo-4-(4-halogen-phenoxy)-phenyl]-2-butoxy-ethyl}-1h [1,2,4]triazole compounds |
SI2776038T1 (en) | 2011-11-11 | 2018-06-29 | Gilead Apollo, Llc | Acc inhibitors and uses thereof |
CN104010502B (en) | 2011-12-21 | 2016-08-24 | 巴斯夫欧洲公司 | Strobilurin-types compound purposes in the plant pathogenic fungi of preventing and treating tolerance Qo inhibitor |
WO2013113781A1 (en) | 2012-02-03 | 2013-08-08 | Basf Se | Fungicidal pyrimidine compounds i |
AR089884A1 (en) | 2012-02-03 | 2014-09-24 | Basf Se | PIRIMIDINE FUNGICIDE COMPOUNDS |
WO2013113782A1 (en) | 2012-02-03 | 2013-08-08 | Basf Se | Fungicidal pyrimidine compounds |
WO2013113716A1 (en) | 2012-02-03 | 2013-08-08 | Basf Se | Fungicidal pyrimidine compounds |
WO2013113773A1 (en) | 2012-02-03 | 2013-08-08 | Basf Se | Fungicidal pyrimidine compounds |
WO2013113720A1 (en) | 2012-02-03 | 2013-08-08 | Basf Se | Fungicidal pyrimidine compounds |
WO2013113776A1 (en) | 2012-02-03 | 2013-08-08 | Basf Se | Fungicidal pyrimidine compounds |
WO2013113719A1 (en) | 2012-02-03 | 2013-08-08 | Basf Se | Fungicidal pyrimidine compounds ii |
IN2014DN07224A (en) | 2012-02-03 | 2015-04-24 | Basf Se | |
WO2013113787A1 (en) | 2012-02-03 | 2013-08-08 | Basf Se | Fungicidal pyrimidine compounds |
WO2013113778A1 (en) | 2012-02-03 | 2013-08-08 | Basf Se | Fungicidal pyrimidine compounds |
WO2013124250A2 (en) | 2012-02-20 | 2013-08-29 | Basf Se | Fungicidal substituted thiophenes |
WO2013135672A1 (en) | 2012-03-13 | 2013-09-19 | Basf Se | Fungicidal pyrimidine compounds |
CN104220435A (en) | 2012-03-13 | 2014-12-17 | 巴斯夫欧洲公司 | Fungicidal pyrimidine compounds |
WO2013144223A1 (en) | 2012-03-30 | 2013-10-03 | Basf Se | N-substituted pyrimidinylidene compounds and derivatives for combating animal pests |
EP2830421B1 (en) | 2012-03-30 | 2017-03-01 | Basf Se | N-substituted pyridinylidene thiocarbonyl compounds and their use for combating animal pests |
US20150065343A1 (en) | 2012-04-02 | 2015-03-05 | Basf Se | Acrylamide compounds for combating invertebrate pests |
EP2834228A1 (en) | 2012-04-03 | 2015-02-11 | Basf Se | N- substituted hetero - bicyclic furanone derivatives for combating animal |
WO2013150115A1 (en) | 2012-04-05 | 2013-10-10 | Basf Se | N- substituted hetero - bicyclic compounds and derivatives for combating animal pests |
MX2014013430A (en) | 2012-05-04 | 2015-04-14 | Basf Se | Substituted pyrazole-containing compounds and their use as pesticides. |
EP2855474B1 (en) | 2012-05-24 | 2017-10-18 | Basf Se | N-thio-anthranilamide compounds and their use as pesticides |
JP2015525223A (en) | 2012-06-14 | 2015-09-03 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | Pest control method using substituted 3-pyridylthiazole compounds and derivatives for controlling animal pests |
WO2014009293A1 (en) | 2012-07-13 | 2014-01-16 | Basf Se | New substituted thiadiazoles and their use as fungicides |
US20150208656A1 (en) | 2012-07-13 | 2015-07-30 | Basf Se | Substituted thiadiazoles and their use as fungicides |
WO2014053407A1 (en) | 2012-10-01 | 2014-04-10 | Basf Se | N-thio-anthranilamide compounds and their use as pesticides |
JP2015535838A (en) | 2012-10-01 | 2015-12-17 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | Pesticidal mixture containing anthranilamide compound |
WO2014053401A2 (en) | 2012-10-01 | 2014-04-10 | Basf Se | Method of improving plant health |
AU2013326645A1 (en) | 2012-10-01 | 2015-04-23 | Basf Se | Pesticidally active mixtures comprising anthranilamide compounds |
AR093771A1 (en) | 2012-10-01 | 2015-06-24 | Basf Se | METHOD TO CONTROL INSECTICIDE RESISTANT INSECTS |
AR093243A1 (en) | 2012-10-01 | 2015-05-27 | Basf Se | USE OF N-TIO-ANTRANILAMIDE COMPOUNDS IN CULTIVATED PLANTS |
CN104768379A (en) | 2012-10-01 | 2015-07-08 | 巴斯夫欧洲公司 | Method of controlling ryanodine-modulator insecticide resistant insects |
WO2014056780A1 (en) | 2012-10-12 | 2014-04-17 | Basf Se | A method for combating phytopathogenic harmful microbes on cultivated plants or plant propagation material |
WO2014079820A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Use of anthranilamide compounds for reducing insect-vectored viral infections |
EP2925730A1 (en) | 2012-11-27 | 2015-10-07 | Basf Se | Substituted 2-[phenoxy-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds and their use as fungicides |
EP2925732A1 (en) | 2012-11-27 | 2015-10-07 | Basf Se | Substituted [1,2,4]triazole compounds |
WO2014082879A1 (en) | 2012-11-27 | 2014-06-05 | Basf Se | Substituted [1,2,4]triazole compounds |
WO2014082881A1 (en) | 2012-11-27 | 2014-06-05 | Basf Se | Substituted 2-[phenoxy-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds and their use as fungicides |
AU2013354353A1 (en) | 2012-12-04 | 2015-07-02 | Basf Se | New substituted 1,4-dithiine derivatives and their use as fungicides |
WO2014086856A1 (en) | 2012-12-04 | 2014-06-12 | Basf Agro B.V., Arnhem (Nl) | Compositions comprising a quillay extract and a biopesticide |
WO2014086850A1 (en) | 2012-12-04 | 2014-06-12 | Basf Agro B.V., Arnhem (Nl) | Compositions comprising a quillay extract and a fungicidal inhibitor of respiratory complex ii |
WO2014086854A1 (en) | 2012-12-04 | 2014-06-12 | Basf Agro B.V., Arnhem (Nl) | Compositions comprising a quillay extract and a plant growth regulator |
WO2014095548A1 (en) | 2012-12-19 | 2014-06-26 | Basf Se | Substituted [1,2,4]triazole compounds and their use as fungicides |
WO2014095381A1 (en) | 2012-12-19 | 2014-06-26 | Basf Se | Fungicidal imidazolyl and triazolyl compounds |
EP2745691A1 (en) | 2012-12-19 | 2014-06-25 | Basf Se | Substituted imidazole compounds and their use as fungicides |
EP2746279A1 (en) | 2012-12-19 | 2014-06-25 | Basf Se | Fungicidal imidazolyl and triazolyl compounds |
WO2014095534A1 (en) | 2012-12-19 | 2014-06-26 | Basf Se | New substituted triazoles and imidazoles and their use as fungicides |
EP2746276A1 (en) | 2012-12-19 | 2014-06-25 | Basf Se | New substituted triazoles and imidazoles and their use as fungicides |
EP2935224A1 (en) | 2012-12-19 | 2015-10-28 | Basf Se | New substituted triazoles and imidazoles and their use as fungicides |
EP2746275A1 (en) | 2012-12-19 | 2014-06-25 | Basf Se | New substituted triazoles and imidazoles and their use as fungicides |
EP2746263A1 (en) | 2012-12-19 | 2014-06-25 | Basf Se | Alpha-substituted triazoles and imidazoles |
EP2746278A1 (en) | 2012-12-19 | 2014-06-25 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
WO2014095555A1 (en) | 2012-12-19 | 2014-06-26 | Basf Se | New substituted triazoles and imidazoles and their use as fungicides |
EP2746266A1 (en) | 2012-12-19 | 2014-06-25 | Basf Se | New substituted triazoles and imidazoles and their use as fungicides |
EP2746277A1 (en) | 2012-12-19 | 2014-06-25 | Basf Se | Fungicidal imidazolyl and triazolyl compounds |
EP2746264A1 (en) | 2012-12-19 | 2014-06-25 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
EP2746255A1 (en) | 2012-12-19 | 2014-06-25 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
EP2746262A1 (en) | 2012-12-19 | 2014-06-25 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds for combating phytopathogenic fungi |
EP2746274A1 (en) | 2012-12-19 | 2014-06-25 | Basf Se | Substituted [1,2,4]triazole compounds |
EP2935237A1 (en) | 2012-12-19 | 2015-10-28 | Basf Se | Substituted [1,2,4]triazole compounds and their use as fungicides |
EP2746256A1 (en) | 2012-12-19 | 2014-06-25 | Basf Se | Fungicidal imidazolyl and triazolyl compounds |
MX2015008100A (en) | 2012-12-20 | 2016-05-31 | Basf Agro Bv | Compositions comprising a triazole compound. |
EP2746258A1 (en) | 2012-12-21 | 2014-06-25 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
EP2746260A1 (en) | 2012-12-21 | 2014-06-25 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
EP2746257A1 (en) | 2012-12-21 | 2014-06-25 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
EP2746259A1 (en) | 2012-12-21 | 2014-06-25 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
US20150368236A1 (en) | 2012-12-27 | 2015-12-24 | Basf Se | 2-(pyridin-3-yl)-5-hetaryl-thiazole compounds carrying an imine or imine-derived substituent for combating invertebrate pests |
WO2014118099A1 (en) | 2013-01-30 | 2014-08-07 | Basf Se | Fungicidal naphthoquinones and derivatives |
WO2014124850A1 (en) | 2013-02-14 | 2014-08-21 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
CN105072915B (en) | 2013-03-20 | 2018-05-01 | 巴斯夫公司 | Synergistic composition comprising bacillus subtilis strain and biological pesticide |
BR112015019289B1 (en) | 2013-03-20 | 2021-05-18 | Basf Corporation | mixture to treat seeds, agrochemical composition and methods for the control of phytopathogenic fungi and for the protection of vegetable seeds |
EP2783569A1 (en) | 2013-03-28 | 2014-10-01 | Basf Se | Compositions comprising a triazole compound |
BR112015026357A2 (en) | 2013-04-19 | 2017-07-25 | Basf Se | compost, agricultural or veterinary composition, methods for the control or control of pests, the protection of plants, the protection of propagating material and the treatment of animals and the use of a compost |
CN105358143B (en) | 2013-05-10 | 2019-01-22 | 吉利德阿波罗公司 | ACC inhibitor and its purposes |
EP2813499A1 (en) | 2013-06-12 | 2014-12-17 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
EP2815649A1 (en) | 2013-06-18 | 2014-12-24 | Basf Se | Fungicidal mixtures II comprising strobilurin-type fungicides |
EP2815647A1 (en) | 2013-06-18 | 2014-12-24 | Basf Se | Novel strobilurin-type compounds for combating phytopathogenic fungi |
WO2014202751A1 (en) | 2013-06-21 | 2014-12-24 | Basf Se | Methods for controlling pests in soybean |
AU2014292164C1 (en) | 2013-07-15 | 2018-09-27 | Basf Se | Pesticide compounds |
WO2015011615A1 (en) | 2013-07-22 | 2015-01-29 | Basf Corporation | Mixtures comprising a trichoderma strain and a pesticide |
EP2835052A1 (en) | 2013-08-07 | 2015-02-11 | Basf Se | Fungicidal mixtures comprising pyrimidine fungicides |
EP2839745A1 (en) | 2013-08-21 | 2015-02-25 | Basf Se | Agrochemical formulations comprising a 2-ethyl-hexanol alkoxylate |
WO2015036059A1 (en) | 2013-09-16 | 2015-03-19 | Basf Se | Fungicidal pyrimidine compounds |
EP3046915A1 (en) | 2013-09-16 | 2016-07-27 | Basf Se | Fungicidal pyrimidine compounds |
JP6404357B2 (en) | 2013-09-19 | 2018-10-10 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | N-Acylimino Heterocyclic Compound |
CA2927784C (en) | 2013-10-18 | 2023-11-14 | Basf Agrochemical Products B.V. | Use of pesticidal active carboxamide derivative in soil and seed application and treatment methods |
WO2015086462A1 (en) | 2013-12-12 | 2015-06-18 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
US20160318897A1 (en) | 2013-12-18 | 2016-11-03 | Basf Se | Azole compounds carrying an imine-derived substituent |
WO2015091649A1 (en) | 2013-12-18 | 2015-06-25 | Basf Se | N-substituted imino heterocyclic compounds |
WO2015104422A1 (en) | 2014-01-13 | 2015-07-16 | Basf Se | Dihydrothiophene compounds for controlling invertebrate pests |
JP2017515794A (en) | 2014-03-26 | 2017-06-15 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | Substituted [1,2,4] triazole and imidazole compounds as fungicides |
EP2924027A1 (en) | 2014-03-28 | 2015-09-30 | Basf Se | Substituted [1,2,4]triazole and imidazole fungicidal compounds |
EP2949649A1 (en) | 2014-05-30 | 2015-12-02 | Basf Se | Fungicide substituted [1,2,4]triazole and imidazole compounds |
EP2949216A1 (en) | 2014-05-30 | 2015-12-02 | Basf Se | Fungicidal substituted alkynyl [1,2,4]triazole and imidazole compounds |
EP2952507A1 (en) | 2014-06-06 | 2015-12-09 | Basf Se | Substituted [1,2,4]triazole compounds |
EP2952512A1 (en) | 2014-06-06 | 2015-12-09 | Basf Se | Substituted [1,2,4]triazole compounds |
AR100743A1 (en) | 2014-06-06 | 2016-10-26 | Basf Se | COMPOUNDS OF [1,2,4] SUBSTITUTED TRIAZOL |
BR112016027983B1 (en) | 2014-06-06 | 2021-11-03 | Basf Se | USE OF COMPOUNDS, AGROCHEMICAL COMPOSITION AND METHOD TO COMBAT PHYTOPATHOGENIC FUNGI |
EP2952506A1 (en) | 2014-06-06 | 2015-12-09 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
EP2979549A1 (en) | 2014-07-31 | 2016-02-03 | Basf Se | Method for improving the health of a plant |
CN106795178B (en) | 2014-10-06 | 2020-05-26 | 巴斯夫欧洲公司 | Substituted pyrimidinium compounds for controlling animal pests |
CN107075712A (en) | 2014-10-24 | 2017-08-18 | 巴斯夫欧洲公司 | Change solid particle surface charge non-both sexes, can quaternary and water-soluble polymer |
WO2016071499A1 (en) | 2014-11-06 | 2016-05-12 | Basf Se | 3-pyridyl heterobicyclic compound for controlling invertebrate pests |
EP3028573A1 (en) | 2014-12-05 | 2016-06-08 | Basf Se | Use of a triazole fungicide on transgenic plants |
JP6743032B2 (en) | 2015-02-06 | 2020-08-19 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | Pyrazole compounds as nitrification inhibitors |
WO2016128240A1 (en) | 2015-02-11 | 2016-08-18 | Basf Se | Pesticidal mixture comprising a pyrazole compound and two fungicides |
WO2016128261A2 (en) | 2015-02-11 | 2016-08-18 | Basf Se | Pesticidal mixture comprising a pyrazole compound, an insecticide and a fungicide |
BR112017021450B1 (en) | 2015-04-07 | 2021-12-28 | Basf Agrochemical Products B.V. | PEST CONTROL METHODS, PLANT HEALTH IMPROVEMENT METHOD AND COATED SEED |
RU2017143177A (en) | 2015-05-12 | 2019-06-13 | Басф Се | Thioether compounds as inhibitors of nitrification |
WO2016198613A1 (en) | 2015-06-11 | 2016-12-15 | Basf Se | N-(thio)acylimino compounds |
WO2016198611A1 (en) | 2015-06-11 | 2016-12-15 | Basf Se | N-(thio)acylimino heterocyclic compounds |
WO2017016883A1 (en) | 2015-07-24 | 2017-02-02 | Basf Se | Process for preparation of cyclopentene compounds |
CA2999378A1 (en) | 2015-10-02 | 2017-04-06 | Basf Se | Imino compounds with a 2-chloropyrimidin-5-yl substituent as pest-control agents |
WO2017060148A1 (en) | 2015-10-05 | 2017-04-13 | Basf Se | Pyridine derivatives for combating phytopathogenic fungi |
WO2017076757A1 (en) | 2015-11-02 | 2017-05-11 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
EP3165094A1 (en) | 2015-11-03 | 2017-05-10 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
EP3370525A1 (en) | 2015-11-04 | 2018-09-12 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
EP3165093A1 (en) | 2015-11-05 | 2017-05-10 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
EP3167716A1 (en) | 2015-11-10 | 2017-05-17 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
US20180354921A1 (en) | 2015-11-13 | 2018-12-13 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
US20180354920A1 (en) | 2015-11-13 | 2018-12-13 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
BR112018008449B1 (en) | 2015-11-19 | 2021-07-06 | Basf Se | COMPOUNDS OF FORMULA I, MIXTURE, AGROCHEMICAL COMPOSITION AND METHOD TO COMBAT HARMFUL PHYTOPATHOGENIC FUNDS |
KR20180083417A (en) | 2015-11-19 | 2018-07-20 | 바스프 에스이 | Substituted oxadiazoles for combating phytopathogenic fungi |
MX2018006286A (en) | 2015-11-25 | 2018-09-07 | Gilead Apollo Llc | Pyrazole acc inhibitors and uses thereof. |
EA201890949A1 (en) | 2015-11-25 | 2018-12-28 | Джилид Аполло, Ллс | ESSENTIAL ETHERIC ACETYL-COA-CARBOXYLASE INHIBITORS AND THEIR OPTIONS |
KR20180082557A (en) | 2015-11-25 | 2018-07-18 | 길리어드 아폴로, 엘엘씨 | Triazole ACC inhibitors and uses thereof |
EP3383183B1 (en) | 2015-11-30 | 2020-05-27 | Basf Se | Compositions containing cis-jasmone and bacillus amyloliquefaciens |
WO2017093120A1 (en) | 2015-12-01 | 2017-06-08 | Basf Se | Pyridine compounds as fungicides |
CN108290840A (en) | 2015-12-01 | 2018-07-17 | 巴斯夫欧洲公司 | Pyridine compounds as fungicide |
EP3205208A1 (en) | 2016-02-09 | 2017-08-16 | Basf Se | Mixtures and compositions comprising paenibacillus strains or fusaricidins and chemical pesticides |
CN108699075A (en) | 2016-03-09 | 2018-10-23 | 巴斯夫欧洲公司 | Spirocyclic derivatives |
WO2017153200A1 (en) | 2016-03-10 | 2017-09-14 | Basf Se | Fungicidal mixtures iii comprising strobilurin-type fungicides |
CN108697089A (en) | 2016-03-11 | 2018-10-23 | 巴斯夫欧洲公司 | The method for preventing and kill off plant insect |
KR102411744B1 (en) | 2016-04-01 | 2022-06-21 | 바스프 에스이 | bicyclic compounds |
AU2017250397A1 (en) | 2016-04-11 | 2018-10-11 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
RU2018143590A (en) | 2016-05-18 | 2020-06-18 | Басф Се | CAPSULES CONTAINING SIMPLE BENZYL PROPARGYL ETHERS INTENDED FOR USE AS NITRIFICATION INHIBITORS |
US20190200612A1 (en) | 2016-09-13 | 2019-07-04 | Basf Se | Fungicidal mixtures i comprising quinoline fungicides |
WO2018054711A1 (en) | 2016-09-26 | 2018-03-29 | Basf Se | Pyridine compounds for controlling phytopathogenic harmful fungi |
WO2018054723A1 (en) | 2016-09-26 | 2018-03-29 | Basf Se | Pyridine compounds for controlling phytopathogenic harmful fungi |
WO2018054721A1 (en) | 2016-09-26 | 2018-03-29 | Basf Se | Pyridine compounds for controlling phytopathogenic harmful fungi |
WO2018065182A1 (en) | 2016-10-04 | 2018-04-12 | Basf Se | Reduced quinoline compounds as antifuni agents |
WO2018073110A1 (en) | 2016-10-20 | 2018-04-26 | Basf Se | Quinoline compounds as fungicides |
WO2018108671A1 (en) | 2016-12-16 | 2018-06-21 | Basf Se | Pesticidal compounds |
WO2018114393A1 (en) | 2016-12-19 | 2018-06-28 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
EP3339297A1 (en) | 2016-12-20 | 2018-06-27 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
EP3338552A1 (en) | 2016-12-21 | 2018-06-27 | Basf Se | Use of a tetrazolinone fungicide on transgenic plants |
CN110191881A (en) | 2017-01-23 | 2019-08-30 | 巴斯夫欧洲公司 | Antifungal pyridine compounds |
WO2018149754A1 (en) | 2017-02-16 | 2018-08-23 | Basf Se | Pyridine compounds |
WO2018153730A1 (en) | 2017-02-21 | 2018-08-30 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
WO2018162312A1 (en) | 2017-03-10 | 2018-09-13 | Basf Se | Spirocyclic derivatives |
WO2018166855A1 (en) | 2017-03-16 | 2018-09-20 | Basf Se | Heterobicyclic substituted dihydroisoxazoles |
CN110506038B (en) | 2017-03-28 | 2023-11-24 | 巴斯夫欧洲公司 | Pesticidal compounds |
MX2019011785A (en) | 2017-03-31 | 2019-11-18 | Basf Se | Process for preparing chiral 2,3-dihydrothiazolo[3,2-a]pyrimidin- 4-ium compounds. |
EP3606914A1 (en) | 2017-04-06 | 2020-02-12 | Basf Se | Pyridine compounds |
MX2019012468A (en) | 2017-04-20 | 2019-12-11 | Pi Industries Ltd | Novel phenylamine compounds. |
WO2018192793A1 (en) | 2017-04-20 | 2018-10-25 | Basf Se | Substituted rhodanine derivatives |
EA201992550A1 (en) | 2017-05-02 | 2020-04-14 | Басф Се | FUNGICIDIC MIXTURES CONTAINING SUBSTITUTED 3-PHENYL-5- (TRIFFORMETHYL) -1,2,4-OXADIAZOZOLES |
WO2018202737A1 (en) | 2017-05-05 | 2018-11-08 | Basf Se | Fungicidal mixtures comprising triazole compounds |
EP3625215B1 (en) | 2017-05-18 | 2023-09-13 | PI Industries Ltd | Formimidamidine compounds useful against phytopathogenic microorganisms |
WO2018219797A1 (en) | 2017-06-02 | 2018-12-06 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
US20210179620A1 (en) | 2017-06-16 | 2021-06-17 | Basf Se | Mesoionic imidazolium compounds and derivatives for combating animal pests |
EP3642187A1 (en) | 2017-06-19 | 2020-04-29 | Basf Se | 2-[[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]aryloxy](thio)acetamides for combating phytopathogenic fungi |
CN110678469B (en) | 2017-06-19 | 2023-03-03 | 巴斯夫欧洲公司 | Substituted pyrimidinium compounds and derivatives for combating animal pests |
WO2018234488A1 (en) | 2017-06-23 | 2018-12-27 | Basf Se | Substituted cyclopropyl derivatives |
WO2019002158A1 (en) | 2017-06-30 | 2019-01-03 | Basf Se | Substituted trifluoromethyloxadiazoles for combating phytopathogenic fungi |
WO2019025250A1 (en) | 2017-08-04 | 2019-02-07 | Basf Se | Substituted trifluoromethyloxadiazoles for combating phytopathogenic fungi |
WO2019038042A1 (en) | 2017-08-21 | 2019-02-28 | Basf Se | Substituted trifluoromethyloxadiazoles for combating phytopathogenic fungi |
EP3915379A1 (en) | 2017-08-29 | 2021-12-01 | Basf Se | Pesticidal mixtures |
WO2019042932A1 (en) | 2017-08-31 | 2019-03-07 | Basf Se | Method of controlling rice pests in rice |
EP3453706A1 (en) | 2017-09-08 | 2019-03-13 | Basf Se | Pesticidal imidazole compounds |
WO2019052932A1 (en) | 2017-09-18 | 2019-03-21 | Basf Se | Substituted trifluoromethyloxadiazoles for combating phytopathogenic fungi |
WO2019057660A1 (en) | 2017-09-25 | 2019-03-28 | Basf Se | Indole and azaindole compounds with substituted 6-membered aryl and heteroaryl rings as agrochemical fungicides |
EP3694852A1 (en) | 2017-10-13 | 2020-08-19 | Basf Se | Imidazolidine pyrimidinium compounds for combating animal pests |
US11147275B2 (en) | 2017-11-23 | 2021-10-19 | Basf Se | Substituted trifluoromethyloxadiazoles for combating phytopathogenic fungi |
WO2019115511A1 (en) | 2017-12-14 | 2019-06-20 | Basf Se | Fungicidal mixture comprising substituted 3-phenyl-5-(trifluoromethyl)-1,2,4-oxadiazoles |
EP3723485A1 (en) | 2017-12-15 | 2020-10-21 | Basf Se | Fungicidal mixture comprising substituted pyridines |
WO2019121143A1 (en) | 2017-12-20 | 2019-06-27 | Basf Se | Substituted cyclopropyl derivatives |
BR112020012614A2 (en) | 2017-12-20 | 2020-11-24 | Pi Industries Ltd | fluoralkenyl compounds, preparation process and use |
EP3728199A1 (en) | 2017-12-21 | 2020-10-28 | Basf Se | Pesticidal compounds |
CN111526719B (en) | 2018-01-09 | 2022-08-16 | 巴斯夫欧洲公司 | Silylethynyl heteroaryl compounds as nitrification inhibitors |
WO2019137995A1 (en) | 2018-01-11 | 2019-07-18 | Basf Se | Novel pyridazine compounds for controlling invertebrate pests |
US11286242B2 (en) | 2018-01-30 | 2022-03-29 | Pi Industries Ltd. | Oxadiazoles for use in controlling phytopathogenic fungi |
WO2019150311A1 (en) | 2018-02-02 | 2019-08-08 | Pi Industries Ltd. | 1-3 dithiol compounds and their use for the protection of crops from phytopathogenic microorganisms |
WO2019154665A1 (en) | 2018-02-07 | 2019-08-15 | Basf Se | New pyridine carboxamides |
US20200354321A1 (en) | 2018-02-07 | 2020-11-12 | Basf Se | New pyridine carboxamides |
EP3530118A1 (en) | 2018-02-26 | 2019-08-28 | Basf Se | Fungicidal mixtures |
EP3530116A1 (en) | 2018-02-27 | 2019-08-28 | Basf Se | Fungicidal mixtures comprising xemium |
BR112020015467A2 (en) | 2018-02-28 | 2020-12-08 | Basf Se | FUNGICIDAL MIXTURES, FUNGICIDAL COMPOSITION, METHODS TO CONTROL PHYTOPATOGENIC FUNGI, TO IMPROVE PLANT HEALTH AND TO PROTECT PLANT PROPAGATION MATERIAL AGAINST PHYTOPHOGENIC FUNGI AND PLANT PROPAGATION MATERIAL |
AU2019226359B2 (en) | 2018-02-28 | 2023-08-17 | Basf Se | Use of N-functionalized alkoxy pyrazole compounds as nitrification inhibitors |
CA3089381A1 (en) | 2018-02-28 | 2019-09-06 | Basf Se | Use of pyrazole propargyl ethers as nitrification inhibitors |
KR20200128052A (en) | 2018-02-28 | 2020-11-11 | 바스프 에스이 | Use of alkoxypyrazoles as nitrification inhibitors |
CN111801014B (en) | 2018-03-01 | 2022-05-27 | 巴斯夫农业公司 | Fungicidal compositions of cloroxen |
EP3533333A1 (en) | 2018-03-02 | 2019-09-04 | Basf Se | Fungicidal mixtures comprising pydiflumetofen |
EP3533331A1 (en) | 2018-03-02 | 2019-09-04 | Basf Se | Fungicidal mixtures comprising pydiflumetofen |
EP3536150A1 (en) | 2018-03-06 | 2019-09-11 | Basf Se | Fungicidal mixtures comprising fluxapyroxad |
EP3762367A1 (en) | 2018-03-09 | 2021-01-13 | PI Industries Ltd. | Heterocyclic compounds as fungicides |
WO2019175712A1 (en) | 2018-03-14 | 2019-09-19 | Basf Corporation | New uses for catechol molecules as inhibitors to glutathione s-transferase metabolic pathways |
WO2019175713A1 (en) | 2018-03-14 | 2019-09-19 | Basf Corporation | New catechol molecules and their use as inhibitors to p450 related metabolic pathways |
WO2019185413A1 (en) | 2018-03-27 | 2019-10-03 | Basf Se | Pesticidal substituted cyclopropyl derivatives |
WO2019202459A1 (en) | 2018-04-16 | 2019-10-24 | Pi Industries Ltd. | Use of 4-substituted phenylamidine compounds for controlling disease rust diseases in plants |
JP7433244B2 (en) | 2018-05-15 | 2024-02-19 | ビーエーエスエフ ソシエタス・ヨーロピア | Mixtures containing benzpyrimoxane and oxazosulfil and methods of use and application thereof |
WO2019219464A1 (en) | 2018-05-15 | 2019-11-21 | Basf Se | Substituted trifluoromethyloxadiazoles for combating phytopathogenic fungi |
WO2019224092A1 (en) | 2018-05-22 | 2019-11-28 | Basf Se | Pesticidally active c15-derivatives of ginkgolides |
WO2020002472A1 (en) | 2018-06-28 | 2020-01-02 | Basf Se | Use of alkynylthiophenes as nitrification inhibitors |
WO2020020777A1 (en) | 2018-07-23 | 2020-01-30 | Basf Se | Use of substituted 2-thiazolines as nitrification inhibitors |
EP3826982B1 (en) | 2018-07-23 | 2023-11-01 | Basf Se | Use of a substituted thiazolidine compound as nitrification inhibitor |
AR115984A1 (en) | 2018-08-17 | 2021-03-17 | Pi Industries Ltd | 1,2-DITIOLONE COMPOUNDS AND THEIR USES |
EP3613736A1 (en) | 2018-08-22 | 2020-02-26 | Basf Se | Substituted glutarimide derivatives |
EP3628158A1 (en) | 2018-09-28 | 2020-04-01 | Basf Se | Pesticidal mixture comprising a mesoionic compound and a biopesticide |
EP3628156A1 (en) | 2018-09-28 | 2020-04-01 | Basf Se | Method for controlling pests of sugarcane, citrus, rapeseed, and potato plants |
WO2020064492A1 (en) | 2018-09-28 | 2020-04-02 | Basf Se | Method of controlling pests by seed treatment application of a mesoionic compound or mixture thereof |
EP3628157A1 (en) | 2018-09-28 | 2020-04-01 | Basf Se | Method of controlling insecticide resistant insects and virus transmission to plants |
CA3112924A1 (en) | 2018-10-01 | 2020-04-09 | Pi Industries Ltd | Oxadiazoles as fungicides |
JP2022501410A (en) | 2018-10-01 | 2022-01-06 | ピーアイ インダストリーズ リミテッドPi Industries Ltd | New oxadiazole |
EP3643705A1 (en) | 2018-10-24 | 2020-04-29 | Basf Se | Pesticidal compounds |
WO2020095161A1 (en) | 2018-11-05 | 2020-05-14 | Pi Industries Ltd. | Nitrone compounds and use thereof |
WO2020109039A1 (en) | 2018-11-28 | 2020-06-04 | Basf Se | Pesticidal compounds |
EP3670501A1 (en) | 2018-12-17 | 2020-06-24 | Basf Se | Substituted [1,2,4]triazole compounds as fungicides |
EP3898623A1 (en) | 2018-12-18 | 2021-10-27 | Basf Se | Substituted pyrimidinium compounds for combating animal pests |
EP3696177A1 (en) | 2019-02-12 | 2020-08-19 | Basf Se | Heterocyclic compounds for the control of invertebrate pests |
US20220151234A1 (en) | 2019-04-08 | 2022-05-19 | Pi Industries Ltd. | Novel oxadiazole compounds for controlling or preventing phytopathogenic fungi |
BR112021020230A2 (en) | 2019-04-08 | 2021-12-07 | Pi Industries Ltd | Innovative Oxadiazole Compounds to Control or Prevent Phytopathogenic Fungi |
US20220151236A1 (en) | 2019-04-08 | 2022-05-19 | Pi Industries Ltd. | Novel oxadiazole compounds for controlling or preventing phytopathogenic fungi |
EP3730489A1 (en) | 2019-04-25 | 2020-10-28 | Basf Se | Heteroaryl compounds as agrochemical fungicides |
BR112021019416A2 (en) | 2019-05-29 | 2021-12-07 | Basf Se | Compounds, composition, methods of protecting crops and combating, controlling, preventing or protecting against infestations, non-therapeutic method of treating infested animals, seed and use |
EP3769623A1 (en) | 2019-07-22 | 2021-01-27 | Basf Se | Mesoionic imidazolium compounds and derivatives for combating animal pests |
WO2020244969A1 (en) | 2019-06-06 | 2020-12-10 | Basf Se | Pyridine derivatives and their use as fungicides |
WO2020244970A1 (en) | 2019-06-06 | 2020-12-10 | Basf Se | New carbocyclic pyridine carboxamides |
CA3140002A1 (en) | 2019-06-06 | 2020-12-10 | Basf Se | Fungicidal n-(pyrid-3-yl)carboxamides |
EP3766879A1 (en) | 2019-07-19 | 2021-01-20 | Basf Se | Pesticidal pyrazole derivatives |
AR119774A1 (en) | 2019-08-19 | 2022-01-12 | Pi Industries Ltd | OXADIAZOLE COMPOUNDS CONTAINING A 5-MEMBER HETEROAROMATIC RING TO CONTROL OR PREVENT PHYTOPATHOGENIC FUNGI |
WO2021063736A1 (en) | 2019-10-02 | 2021-04-08 | Basf Se | Bicyclic pyridine derivatives |
WO2021063735A1 (en) | 2019-10-02 | 2021-04-08 | Basf Se | New bicyclic pyridine derivatives |
AR120374A1 (en) | 2019-11-08 | 2022-02-09 | Pi Industries Ltd | OXADIAZOLE COMPOUNDS CONTAINING FUSED HETEROCYCYL RINGS TO CONTROL OR PREVENT PHYTOPATHOGENIC FUNGI |
CA3162521A1 (en) | 2019-12-23 | 2021-07-01 | Basf Se | Enzyme enhanced root uptake of agrochemical active compound |
US20230106291A1 (en) | 2020-02-28 | 2023-04-06 | BASF Agro B.V. | Methods and uses of a mixture comprising alpha-cypermethrin and dinotefuran for controlling invertebrate pests in t |
WO2021175669A1 (en) | 2020-03-04 | 2021-09-10 | Basf Se | Use of substituted 1,2,4-oxadiazoles for combating phytopathogenic fungi |
BR112022020612A2 (en) | 2020-04-14 | 2022-11-29 | Basf Se | FUNGICIDAL MIXTURE, AGROCHEMICAL COMPOSITION, NON-THERAPEUTIC USE OF THE MIXTURE AND METHOD TO CONTROL HARMFUL PHYTOPATHOGENIC FUNGI |
EP3903583A1 (en) | 2020-04-28 | 2021-11-03 | Basf Se | Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors iii |
EP3903584A1 (en) | 2020-04-28 | 2021-11-03 | Basf Se | Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors iv |
EP3903582A1 (en) | 2020-04-28 | 2021-11-03 | Basf Se | Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors ii |
EP3903581A1 (en) | 2020-04-28 | 2021-11-03 | Basf Se | Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors i |
WO2021219513A1 (en) | 2020-04-28 | 2021-11-04 | Basf Se | Pesticidal compounds |
EP3909950A1 (en) | 2020-05-13 | 2021-11-17 | Basf Se | Heterocyclic compounds for the control of invertebrate pests |
WO2021249800A1 (en) | 2020-06-10 | 2021-12-16 | Basf Se | Substituted [1,2,4]triazole compounds as fungicides |
EP3945089A1 (en) | 2020-07-31 | 2022-02-02 | Basf Se | Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors v |
EP3939961A1 (en) | 2020-07-16 | 2022-01-19 | Basf Se | Strobilurin type compounds and their use for combating phytopathogenic fungi |
WO2022017836A1 (en) | 2020-07-20 | 2022-01-27 | BASF Agro B.V. | Fungicidal compositions comprising (r)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1- (1,2,4-triazol-1-yl)propan-2-ol |
EP3970494A1 (en) | 2020-09-21 | 2022-03-23 | Basf Se | Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors viii |
AR123264A1 (en) | 2020-08-18 | 2022-11-16 | Pi Industries Ltd | NEW HETEROCYCLIC COMPOUNDS TO COMBAT PHYTOPATHOGENIC FUNGI |
WO2022058878A1 (en) | 2020-09-15 | 2022-03-24 | Pi Industries Limited | Novel picolinamide compounds for combating phytopathogenic fungi |
UY39423A (en) | 2020-09-15 | 2022-03-31 | Pi Industries Ltd | NEW PICOLINAMIDE COMPOUNDS TO COMBAT PHYTOPATHOGENIC FUNGI |
AR123594A1 (en) | 2020-09-26 | 2022-12-21 | Pi Industries Ltd | NEMATICIDAL COMPOUNDS AND THEIR USE |
US20230397607A1 (en) | 2020-10-27 | 2023-12-14 | BASF Agro B.V. | Compositions comprising mefentrifluconazole |
WO2022090069A1 (en) | 2020-11-02 | 2022-05-05 | Basf Se | Compositions comprising mefenpyr-diethyl |
WO2022090071A1 (en) | 2020-11-02 | 2022-05-05 | Basf Se | Use of mefenpyr-diethyl for controlling phytopathogenic fungi |
WO2022106304A1 (en) | 2020-11-23 | 2022-05-27 | BASF Agro B.V. | Compositions comprising mefentrifluconazole |
EP4018830A1 (en) | 2020-12-23 | 2022-06-29 | Basf Se | Pesticidal mixtures |
WO2022167488A1 (en) | 2021-02-02 | 2022-08-11 | Basf Se | Synergistic action of dcd and alkoxypyrazoles as nitrification inhibitors |
EP4043444A1 (en) | 2021-02-11 | 2022-08-17 | Basf Se | Substituted isoxazoline derivatives |
WO2022234470A1 (en) | 2021-05-05 | 2022-11-10 | Pi Industries Ltd. | Novel fused heterocyclic compounds for combating phytopathogenic fungi |
BR112023023592A2 (en) | 2021-05-11 | 2024-03-12 | Basf Se | FUNGICIDAL MIXTURE, AGROCHEMICAL COMPOSITION, USE OF THE MIXTURE AND METHOD TO CONTROL HARMFUL PHYTOPATHOGENIC FUNGI |
CN117355519A (en) | 2021-05-18 | 2024-01-05 | 巴斯夫欧洲公司 | Novel substituted pyridines as fungicides |
WO2022243107A1 (en) | 2021-05-18 | 2022-11-24 | Basf Se | New substituted pyridines as fungicides |
BR112023023989A2 (en) | 2021-05-18 | 2024-01-30 | Basf Se | COMPOUNDS, COMPOSITION, METHOD TO COMBAT PHYTOPATHOGENIC AND SEED FUNGI |
AR125954A1 (en) | 2021-05-21 | 2023-08-30 | Basf Se | USE OF ETHYNYLPYRIDINE COMPOUNDS AS NITRIFICATION INHIBITORS |
WO2022243523A1 (en) | 2021-05-21 | 2022-11-24 | Basf Se | Use of an n-functionalized alkoxy pyrazole compound as nitrification inhibitor |
AR125925A1 (en) | 2021-05-26 | 2023-08-23 | Pi Industries Ltd | FUNGICIDAL COMPOSITION CONTAINING OXADIAZOLE COMPOUNDS |
EP4094579A1 (en) | 2021-05-28 | 2022-11-30 | Basf Se | Pesticidal mixtures comprising metyltetraprole |
EP4358725A1 (en) | 2021-06-21 | 2024-05-01 | Basf Se | Metal-organic frameworks with pyrazole-based building blocks |
EP4119547A1 (en) | 2021-07-12 | 2023-01-18 | Basf Se | Triazole compounds for the control of invertebrate pests |
WO2023011958A1 (en) | 2021-08-02 | 2023-02-09 | Basf Se | (3-pirydyl)-quinazoline |
WO2023011957A1 (en) | 2021-08-02 | 2023-02-09 | Basf Se | (3-quinolyl)-quinazoline |
EP4140986A1 (en) | 2021-08-23 | 2023-03-01 | Basf Se | Pyrazine compounds for the control of invertebrate pests |
EP4140995A1 (en) | 2021-08-27 | 2023-03-01 | Basf Se | Pyrazine compounds for the control of invertebrate pests |
EP4151631A1 (en) | 2021-09-20 | 2023-03-22 | Basf Se | Heterocyclic compounds for the control of invertebrate pests |
WO2023072670A1 (en) | 2021-10-28 | 2023-05-04 | Basf Se | Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors x |
WO2023072671A1 (en) | 2021-10-28 | 2023-05-04 | Basf Se | Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors ix |
EP4194453A1 (en) | 2021-12-08 | 2023-06-14 | Basf Se | Pyrazine compounds for the control of invertebrate pests |
EP4198033A1 (en) | 2021-12-14 | 2023-06-21 | Basf Se | Heterocyclic compounds for the control of invertebrate pests |
EP4198023A1 (en) | 2021-12-16 | 2023-06-21 | Basf Se | Pesticidally active thiosemicarbazone compounds |
AR127972A1 (en) | 2021-12-17 | 2024-03-13 | Pi Industries Ltd | NOVEL FUSED SUBSTITUTED BICYCLIC CARBOXAMIDE PYRIDINE COMPOUNDS TO COMBAT PHYTOPATHOGENIC FUNGI |
EP4238971A1 (en) | 2022-03-02 | 2023-09-06 | Basf Se | Substituted isoxazoline derivatives |
WO2023203066A1 (en) | 2022-04-21 | 2023-10-26 | Basf Se | Synergistic action as nitrification inhibitors of dcd oligomers with alkoxypyrazole and its oligomers |
WO2023208447A1 (en) | 2022-04-25 | 2023-11-02 | Basf Se | An emulsifiable concentrate having a (substituted) benzaldehyde-based solvent system |
WO2024028243A1 (en) | 2022-08-02 | 2024-02-08 | Basf Se | Pyrazolo pesticidal compounds |
EP4342885A1 (en) | 2022-09-20 | 2024-03-27 | Basf Se | N-(3-(aminomethyl)-phenyl)-5-(4-phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-amine derivatives and similar compounds as pesticides |
EP4361126A1 (en) | 2022-10-24 | 2024-05-01 | Basf Se | Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors xv |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DD155030A1 (en) * | 1980-12-05 | 1982-05-12 | Reingard Beyer | BIOZIDE MEDIUM |
AU600170B2 (en) * | 1987-09-25 | 1990-08-02 | Mitsui Toatsu Chemicals Inc. | 2-(2,2,2-trifluoroethyl imino)-tetrahydro-1,3,5, thiadiazin- 4-ones and their preparation and use |
JP2610988B2 (en) * | 1989-03-09 | 1997-05-14 | 日本バイエルアグロケム 株式会社 | New heterocyclic compounds and insecticides |
WO1991001978A1 (en) * | 1989-07-28 | 1991-02-21 | Nippon Soda Co., Ltd. | Triazine derivatives |
-
1990
- 1990-10-31 US US07/606,848 patent/US6187773B1/en not_active Expired - Fee Related
- 1990-10-31 AU AU65623/90A patent/AU628229B2/en not_active Expired
- 1990-11-08 EP EP90121383A patent/EP0428941B1/en not_active Expired - Lifetime
- 1990-11-08 DE DE69019107T patent/DE69019107T2/en not_active Expired - Lifetime
- 1990-11-10 CN CN90109039A patent/CN1026648C/en not_active Expired - Lifetime
-
1994
- 1994-03-25 CN CN94103331A patent/CN1050600C/en not_active Expired - Lifetime
-
2000
- 2000-12-06 US US09/729,865 patent/US20010046994A1/en not_active Abandoned
Cited By (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6716874B1 (en) | 1999-03-24 | 2004-04-06 | Bayer Aktiengesellschaft | Synergistic insecticide mixtures |
US6894074B2 (en) | 1999-03-24 | 2005-05-17 | Bayer Aktiengesellschaft | Synergistic insecticidal mixtures |
US8841294B2 (en) | 1999-10-07 | 2014-09-23 | Bayer Cropscience Ag | Active ingredient combinations having insecticidal and acaricidal properties |
US6893651B1 (en) | 1999-10-07 | 2005-05-17 | Bayer Aktiengesellschaft | Active ingredient combinations having insecticidal and acaricidal properties |
US20050187215A1 (en) * | 1999-10-07 | 2005-08-25 | Reiner Fischer | Active ingredient combinations having insecticidal and acaricidal properties |
US6528651B1 (en) | 1999-12-21 | 2003-03-04 | Bayer Aktiengesellschaft | Method for production of 1,3-disubtituted 2-nitroguanidines |
US20040167177A1 (en) * | 2001-05-03 | 2004-08-26 | Jorn Stolting | Method for producing 1,3-disubstituted 2-nitroguanidines |
US7026307B2 (en) | 2001-05-03 | 2006-04-11 | Bayer Cropscience Ag | Method for producing 1,3-disubstituted 2-nitroguanidines |
US8232261B2 (en) | 2003-07-18 | 2012-07-31 | Bayer Cropscience Lp | Method of minimizing herbicidal injury |
US8426339B2 (en) | 2003-07-18 | 2013-04-23 | Bayer Cropscience Lp | Method of minimizing herbicidal injury |
US20050014646A1 (en) * | 2003-07-18 | 2005-01-20 | Schwarz Michael R. | Method of minimizing herbicidal injury |
US20070157507A1 (en) * | 2004-08-25 | 2007-07-12 | Reid Byron L | Method of controlling termites |
US9919979B2 (en) | 2005-01-21 | 2018-03-20 | Bayer Cropscience Lp | Fertilizer-compatible composition |
US20100311580A1 (en) * | 2007-12-11 | 2010-12-09 | Bayer Cropscience Ag | Active Compound Combinations |
US9599560B2 (en) | 2014-06-06 | 2017-03-21 | International Business Machines Corporation | Methods and apparatus for detecting metals in liquids |
GB2542063A (en) * | 2014-06-16 | 2017-03-08 | Ibm | Methods and apparatus for controlling metals in liquids |
CN106458660A (en) * | 2014-06-16 | 2017-02-22 | 国际商业机器公司 | Methods and apparatus for controlling metals in liquids |
US9656239B2 (en) | 2014-06-16 | 2017-05-23 | International Business Machines Corporation | Apparatus for controlling metals in liquids |
US9770702B2 (en) | 2014-06-16 | 2017-09-26 | International Business Machines Corporation | Methods and apparatus for controlling metals in liquids |
WO2015195378A1 (en) * | 2014-06-16 | 2015-12-23 | International Business Machines Corporation | Methods and apparatus for controlling metals in liquids |
US10328415B2 (en) | 2014-06-16 | 2019-06-25 | International Business Machines Corporation | Methods and apparatus for controlling metals in liquids |
GB2542063B (en) * | 2014-06-16 | 2019-09-11 | Ibm | Methods for controlling metals in liquids |
US10525442B2 (en) | 2014-06-16 | 2020-01-07 | International Business Machines Corporation | Methods and apparatus for controlling metals in liquids |
Also Published As
Publication number | Publication date |
---|---|
CN1060656A (en) | 1992-04-29 |
DE69019107D1 (en) | 1995-06-08 |
AU628229B2 (en) | 1992-09-10 |
DE69019107T2 (en) | 1995-08-31 |
EP0428941A1 (en) | 1991-05-29 |
CN1026648C (en) | 1994-11-23 |
EP0428941B1 (en) | 1995-05-03 |
AU6562390A (en) | 1991-05-16 |
CN1050600C (en) | 2000-03-22 |
US6187773B1 (en) | 2001-02-13 |
CN1098719A (en) | 1995-02-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US6187773B1 (en) | Hexahydrotriazine compounds and insecticides | |
US5166164A (en) | Nitroguanidine compounds useful as insecticides | |
EP0376279B1 (en) | Guanidine derivatives, their production and insecticides | |
JP2610988B2 (en) | New heterocyclic compounds and insecticides | |
US4647570A (en) | Pesticidal novel nitromethylene derivatives | |
US4812454A (en) | Nitromethylene derivatives and their use as insecticides | |
JP2867345B2 (en) | Insecticidal trifluoroacetyl derivative | |
EP0455000B1 (en) | Dialkoxymethylimidazolidine derivatives, preparation thereof, insecticides containing same as an effective ingredient and intermediates therefor | |
KR0135974B1 (en) | Tetrahydropyrimidines, their production and use | |
WO2010001922A1 (en) | Novel imino derivative, process for production of the same, and pesticide comprising the same | |
JP3059559B2 (en) | Insecticidal guanidine derivatives | |
US5264584A (en) | Dialkoxymethylimidazolidine derivatives | |
KR0147056B1 (en) | Hexa hydro triazine compounds and insecticides | |
JPH0514716B2 (en) | ||
KR0157056B1 (en) | 5-nitro-tetrahydropyrimidines and insecticides containing them for agricultural uses | |
CA2032710A1 (en) | Imidazolidine derivatives, process for producing the same and pesticides containing the same | |
JP2961516B2 (en) | New heterocyclic compounds and insecticides | |
JP2707239B2 (en) | Cyanoalkyl-heterocyclic compounds and insecticides | |
JP3437462B2 (en) | Insecticide | |
HU197495B (en) | Insecticide compositions containing /nitro-methylene/-tetrahydropyrimidine derivatives as active components and process for producing the active components | |
JP3352082B2 (en) | New heterocyclic compounds | |
EP0471092B1 (en) | Triazole compound and insecticide | |
JPH06316572A (en) | New heterocyclic compound and insecticide | |
JPH03264580A (en) | Tetrahydropyrimidine compound, production thereof and insecticide | |
JPH0547540B2 (en) |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION |