ES2416083T3 - Pesticidas mesoiónicos - Google Patents
Pesticidas mesoiónicos Download PDFInfo
- Publication number
- ES2416083T3 ES2416083T3 ES09709044T ES09709044T ES2416083T3 ES 2416083 T3 ES2416083 T3 ES 2416083T3 ES 09709044 T ES09709044 T ES 09709044T ES 09709044 T ES09709044 T ES 09709044T ES 2416083 T3 ES2416083 T3 ES 2416083T3
- Authority
- ES
- Spain
- Prior art keywords
- hydroxy
- alkyl
- methyl
- oxo
- chloro
- 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.)
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- 239000000575 pesticide Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 347
- -1 C2- alkynyl C4 Chemical group 0.000 claims abstract description 198
- 125000001424 substituent group Chemical group 0.000 claims abstract description 143
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 136
- 150000002367 halogens Chemical class 0.000 claims abstract description 131
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 116
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 100
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 99
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract description 77
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 70
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims abstract description 68
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 66
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 60
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 60
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 59
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 59
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims abstract description 57
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims abstract description 57
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims abstract description 56
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 56
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 51
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 36
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 30
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 30
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract description 28
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 27
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 25
- 125000000232 haloalkynyl group Chemical group 0.000 claims abstract description 25
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 25
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims abstract description 19
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 19
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 19
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 19
- 125000000262 haloalkenyl group Chemical group 0.000 claims abstract description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 14
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 11
- 239000000203 mixture Substances 0.000 claims description 140
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 82
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 64
- 241000607479 Yersinia pestis Species 0.000 claims description 64
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 58
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 58
- 150000003839 salts Chemical class 0.000 claims description 57
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 47
- 239000007787 solid Substances 0.000 claims description 46
- 229910052757 nitrogen Inorganic materials 0.000 claims description 39
- HCMJWOGOISXSDL-UHFFFAOYSA-N (2-isothiocyanato-1-phenylethyl)benzene Chemical compound C=1C=CC=CC=1C(CN=C=S)C1=CC=CC=C1 HCMJWOGOISXSDL-UHFFFAOYSA-N 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 33
- 241001465754 Metazoa Species 0.000 claims description 30
- 229910052731 fluorine Inorganic materials 0.000 claims description 30
- 239000003085 diluting agent Substances 0.000 claims description 28
- CZPWVGJYEJSRLH-UHFFFAOYSA-O hydron;pyrimidine Chemical compound C1=CN=C[NH+]=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-O 0.000 claims description 27
- 239000007788 liquid Substances 0.000 claims description 27
- 125000001188 haloalkyl group Chemical group 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 229910052801 chlorine Inorganic materials 0.000 claims description 21
- 239000004094 surface-active agent Substances 0.000 claims description 21
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
- 125000004076 pyridyl group Chemical group 0.000 claims description 19
- 125000005647 linker group Chemical group 0.000 claims description 18
- 125000001624 naphthyl group Chemical group 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 230000002633 protecting effect Effects 0.000 claims description 10
- 238000011282 treatment Methods 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 150000001721 carbon Chemical group 0.000 claims description 8
- 230000003071 parasitic effect Effects 0.000 claims description 8
- 238000002560 therapeutic procedure Methods 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
- 125000006809 haloalkylaminocarbonyl group Chemical group 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- ZUVGXYUYJMZUDL-UHFFFAOYSA-O (3e)-1-[(2-chloro-1,3-thiazol-5-yl)methyl]-3-[ethoxy(hydroxy)methylidene]pyrido[1,2-a]pyrimidin-5-ium-2,4-dione Chemical class C=12C=CC=CN2C(=O)C(C(=O)OCC)=C(O)[N+]=1CC1=CN=C(Cl)S1 ZUVGXYUYJMZUDL-UHFFFAOYSA-O 0.000 claims description 2
- BSTBFVSCILKZRP-UHFFFAOYSA-O (3e)-3-(2-chloro-1h-pyridin-4-ylidene)-1-[(2-chloro-1,3-thiazol-5-yl)methyl]pyrido[1,2-a]pyrimidin-5-ium-2,4-dione Chemical class O=C1N2C=CC=CC2=[N+](CC=2SC(Cl)=NC=2)C(O)=C1C1=CC=NC(Cl)=C1 BSTBFVSCILKZRP-UHFFFAOYSA-O 0.000 claims description 2
- RTEYXBFCIGPUOL-UHFFFAOYSA-O (3z)-1-[(2-chloro-1,3-thiazol-5-yl)methyl]-3-[hydroxy(phenyl)methylidene]pyrido[1,2-a]pyrimidin-5-ium-2,4-dione Chemical class O=C1N2C=CC=CC2=[N+](CC=2SC(Cl)=NC=2)C(O)=C1C(=O)C1=CC=CC=C1 RTEYXBFCIGPUOL-UHFFFAOYSA-O 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
- RUKLMINUCFGVDM-UHFFFAOYSA-O 1-[(2-chloro-1,3-thiazol-5-yl)methyl]-2-hydroxy-3-(2,4,5-trifluorophenyl)pyrido[1,2-a]pyrimidin-5-ium-4-one Chemical class O=C1N2C=CC=CC2=[N+](CC=2SC(Cl)=NC=2)C(O)=C1C1=CC(F)=C(F)C=C1F RUKLMINUCFGVDM-UHFFFAOYSA-O 0.000 claims description 2
- PQYIZELLTRXCRL-UHFFFAOYSA-O 1-[(2-chloro-1,3-thiazol-5-yl)methyl]-2-hydroxy-3-(2-methoxyphenyl)pyrido[1,2-a]pyrimidin-5-ium-4-one Chemical class COC1=CC=CC=C1C(C1=O)=C(O)[N+](CC=2SC(Cl)=NC=2)=C2N1C=CC=C2 PQYIZELLTRXCRL-UHFFFAOYSA-O 0.000 claims description 2
- MQXBSJRMPODSMJ-UHFFFAOYSA-O 1-[(2-chloro-1,3-thiazol-5-yl)methyl]-2-hydroxy-3-(3-methoxyphenyl)pyrido[1,2-a]pyrimidin-5-ium-4-one Chemical class COC1=CC=CC(C=2C(N3C=CC=CC3=[N+](CC=3SC(Cl)=NC=3)C=2O)=O)=C1 MQXBSJRMPODSMJ-UHFFFAOYSA-O 0.000 claims description 2
- VQWYQXLNQBMZKD-UHFFFAOYSA-O 1-[(2-chloro-1,3-thiazol-5-yl)methyl]-2-hydroxy-3-(4-methoxyphenyl)pyrido[1,2-a]pyrimidin-5-ium-4-one Chemical class C1=CC(OC)=CC=C1C(C1=O)=C(O)[N+](CC=2SC(Cl)=NC=2)=C2N1C=CC=C2 VQWYQXLNQBMZKD-UHFFFAOYSA-O 0.000 claims description 2
- KAHQXJFLKXEGRC-UHFFFAOYSA-O 1-[(2-chloro-1,3-thiazol-5-yl)methyl]-2-hydroxy-3-[3-(trifluoromethoxy)phenyl]pyrido[1,2-a]pyrimidin-5-ium-4-one Chemical class O=C1N2C=CC=CC2=[N+](CC=2SC(Cl)=NC=2)C(O)=C1C1=CC=CC(OC(F)(F)F)=C1 KAHQXJFLKXEGRC-UHFFFAOYSA-O 0.000 claims description 2
- ZHBZAGWZRBEMIH-UHFFFAOYSA-O 1-[(2-chloro-1,3-thiazol-5-yl)methyl]-2-hydroxy-3-[3-(trifluoromethyl)phenyl]pyrido[1,2-a]pyrimidin-5-ium-4-one Chemical class O=C1N2C=CC=CC2=[N+](CC=2SC(Cl)=NC=2)C(O)=C1C1=CC=CC(C(F)(F)F)=C1 ZHBZAGWZRBEMIH-UHFFFAOYSA-O 0.000 claims description 2
- ZOVGKCUMXKZAQJ-UHFFFAOYSA-O 1-[(2-chloro-1,3-thiazol-5-yl)methyl]-2-hydroxy-3-phenylpyrido[1,2-a]pyrimidin-5-ium-4-one Chemical class O=C1N2C=CC=CC2=[N+](CC=2SC(Cl)=NC=2)C(O)=C1C1=CC=CC=C1 ZOVGKCUMXKZAQJ-UHFFFAOYSA-O 0.000 claims description 2
- DMSJXEUGUYHPCJ-UHFFFAOYSA-O 1-[(2-chloro-1,3-thiazol-5-yl)methyl]-3-(2,4-difluorophenyl)-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical class O=C1N2C=CC=CC2=[N+](CC=2SC(Cl)=NC=2)C(O)=C1C1=CC=C(F)C=C1F DMSJXEUGUYHPCJ-UHFFFAOYSA-O 0.000 claims description 2
- QULKCWKSYBCPJR-UHFFFAOYSA-O 1-[(2-chloro-1,3-thiazol-5-yl)methyl]-3-(2-fluorophenyl)-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical class O=C1N2C=CC=CC2=[N+](CC=2SC(Cl)=NC=2)C(O)=C1C1=CC=CC=C1F QULKCWKSYBCPJR-UHFFFAOYSA-O 0.000 claims description 2
- TZLYXTCAGBXJPW-UHFFFAOYSA-O 1-[(2-chloro-1,3-thiazol-5-yl)methyl]-3-(4-fluorophenyl)-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical class O=C1N2C=CC=CC2=[N+](CC=2SC(Cl)=NC=2)C(O)=C1C1=CC=C(F)C=C1 TZLYXTCAGBXJPW-UHFFFAOYSA-O 0.000 claims description 2
- YJHGWBOIKDYSFY-UHFFFAOYSA-O 1-[(6-chloropyridin-3-yl)methyl]-2-hydroxy-3-(3-methoxyphenyl)pyrido[1,2-a]pyrimidin-5-ium-4-one Chemical class COC1=CC=CC(C=2C(N3C=CC=CC3=[N+](CC=3C=NC(Cl)=CC=3)C=2O)=O)=C1 YJHGWBOIKDYSFY-UHFFFAOYSA-O 0.000 claims description 2
- VWUUKYCKDVZQAW-UHFFFAOYSA-O 1-[(6-chloropyridin-3-yl)methyl]-2-hydroxy-3-[3-(trifluoromethoxy)phenyl]pyrido[1,2-a]pyrimidin-5-ium-4-one Chemical class O=C1N2C=CC=CC2=[N+](CC=2C=NC(Cl)=CC=2)C(O)=C1C1=CC=CC(OC(F)(F)F)=C1 VWUUKYCKDVZQAW-UHFFFAOYSA-O 0.000 claims description 2
- BZAUXNJBLQGKNN-UHFFFAOYSA-O 1-[(6-chloropyridin-3-yl)methyl]-3-(2,3-difluorophenyl)-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical class O=C1N2C=CC=CC2=[N+](CC=2C=NC(Cl)=CC=2)C(O)=C1C1=CC=CC(F)=C1F BZAUXNJBLQGKNN-UHFFFAOYSA-O 0.000 claims description 2
- BZCAZTGDNMZJOI-UHFFFAOYSA-O 1-[(6-chloropyridin-3-yl)methyl]-3-(2,4-difluorophenyl)-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical class O=C1N2C=CC=CC2=[N+](CC=2C=NC(Cl)=CC=2)C(O)=C1C1=CC=C(F)C=C1F BZCAZTGDNMZJOI-UHFFFAOYSA-O 0.000 claims description 2
- RNWSCKVLHVIXJF-UHFFFAOYSA-O 1-[(6-chloropyridin-3-yl)methyl]-3-(2-fluoro-3-methoxyphenyl)-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical class COC1=CC=CC(C=2C(N3C=CC=CC3=[N+](CC=3C=NC(Cl)=CC=3)C=2O)=O)=C1F RNWSCKVLHVIXJF-UHFFFAOYSA-O 0.000 claims description 2
- XYHPZXYCDLMYKE-UHFFFAOYSA-O 1-[(6-chloropyridin-3-yl)methyl]-3-(4-fluorophenyl)-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical class O=C1N2C=CC=CC2=[N+](CC=2C=NC(Cl)=CC=2)C(O)=C1C1=CC=C(F)C=C1 XYHPZXYCDLMYKE-UHFFFAOYSA-O 0.000 claims description 2
- JVOHDMQLZSPJCZ-UHFFFAOYSA-O 1-[(6-fluoropyridin-3-yl)methyl]-2-hydroxy-3-[3-(trifluoromethoxy)phenyl]pyrido[1,2-a]pyrimidin-5-ium-4-one Chemical class O=C1N2C=CC=CC2=[N+](CC=2C=NC(F)=CC=2)C(O)=C1C1=CC=CC(OC(F)(F)F)=C1 JVOHDMQLZSPJCZ-UHFFFAOYSA-O 0.000 claims description 2
- WSQKZWLUHIELGZ-UHFFFAOYSA-O 1-[(6-fluoropyridin-3-yl)methyl]-2-hydroxy-3-[3-(trifluoromethyl)phenyl]pyrido[1,2-a]pyrimidin-5-ium-4-one Chemical class O=C1N2C=CC=CC2=[N+](CC=2C=NC(F)=CC=2)C(O)=C1C1=CC=CC(C(F)(F)F)=C1 WSQKZWLUHIELGZ-UHFFFAOYSA-O 0.000 claims description 2
- GYMYCGXHDYFWIQ-UHFFFAOYSA-O 1-[1-(6-chloropyridin-3-yl)ethyl]-3-(4-fluorophenyl)-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical class OC1=C(C=2C=CC(F)=CC=2)C(=O)N2C=CC=CC2=[N+]1C(C)C1=CC=C(Cl)N=C1 GYMYCGXHDYFWIQ-UHFFFAOYSA-O 0.000 claims description 2
- CTKOGEHIKCYTAS-UHFFFAOYSA-O 2-[1-[(2-chloro-1,3-thiazol-5-yl)methyl]-2-hydroxy-4-oxopyrido[1,2-a]pyrimidin-5-ium-3-yl]benzonitrile Chemical class O=C1N2C=CC=CC2=[N+](CC=2SC(Cl)=NC=2)C(O)=C1C1=CC=CC=C1C#N CTKOGEHIKCYTAS-UHFFFAOYSA-O 0.000 claims description 2
- LFZNBOSTDJTUBR-UHFFFAOYSA-O 2-hydroxy-1-[(1-methylpyrazol-4-yl)methyl]-3-phenylpyrido[1,2-a]pyrimidin-5-ium-4-one Chemical class C1=NN(C)C=C1C[N+]1=C2C=CC=CN2C(=O)C(C=2C=CC=CC=2)=C1O LFZNBOSTDJTUBR-UHFFFAOYSA-O 0.000 claims description 2
- GCBAYZNVUBXELQ-UHFFFAOYSA-O 2-hydroxy-3-phenyl-1-(1,3-thiazol-5-ylmethyl)pyrido[1,2-a]pyrimidin-5-ium-4-one Chemical class O=C1N2C=CC=CC2=[N+](CC=2SC=NC=2)C(O)=C1C1=CC=CC=C1 GCBAYZNVUBXELQ-UHFFFAOYSA-O 0.000 claims description 2
- SPFJNWLEGQABKT-UHFFFAOYSA-O 3-(2,4-difluorophenyl)-1-[(6-fluoropyridin-3-yl)methyl]-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical class O=C1N2C=CC=CC2=[N+](CC=2C=NC(F)=CC=2)C(O)=C1C1=CC=C(F)C=C1F SPFJNWLEGQABKT-UHFFFAOYSA-O 0.000 claims description 2
- IYMPSZUYLDGPPE-UHFFFAOYSA-O 3-(2-fluorophenyl)-1-[(6-fluoropyridin-3-yl)methyl]-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical class O=C1N2C=CC=CC2=[N+](CC=2C=NC(F)=CC=2)C(O)=C1C1=CC=CC=C1F IYMPSZUYLDGPPE-UHFFFAOYSA-O 0.000 claims description 2
- CZGUWQYEUWLNIK-UHFFFAOYSA-O 3-(3,5-dimethoxyphenyl)-1-[(6-fluoropyridin-3-yl)methyl]-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical class COC1=CC(OC)=CC(C=2C(N3C=CC=CC3=[N+](CC=3C=NC(F)=CC=3)C=2O)=O)=C1 CZGUWQYEUWLNIK-UHFFFAOYSA-O 0.000 claims description 2
- JBARDNLYURXCNK-UHFFFAOYSA-O 3-(3-bromophenyl)-1-[(2-chloro-1,3-thiazol-5-yl)methyl]-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical class O=C1N2C=CC=CC2=[N+](CC=2SC(Cl)=NC=2)C(O)=C1C1=CC=CC(Br)=C1 JBARDNLYURXCNK-UHFFFAOYSA-O 0.000 claims description 2
- FXFBCLLJLOGYOA-UHFFFAOYSA-O 3-(3-bromophenyl)-1-[(6-chloropyridin-3-yl)methyl]-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound O=C1N2C=CC=CC2=[N+](CC=2C=NC(Cl)=CC=2)C(O)=C1C1=CC=CC(Br)=C1 FXFBCLLJLOGYOA-UHFFFAOYSA-O 0.000 claims description 2
- ULQAUZNZENQDGX-UHFFFAOYSA-O 3-(3-chlorophenyl)-1-[(2-chloro-1,3-thiazol-5-yl)methyl]-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical class O=C1N2C=CC=CC2=[N+](CC=2SC(Cl)=NC=2)C(O)=C1C1=CC=CC(Cl)=C1 ULQAUZNZENQDGX-UHFFFAOYSA-O 0.000 claims description 2
- PXLXAWRVAPTDFO-UHFFFAOYSA-O 3-(4-fluorophenyl)-2-hydroxy-1-(1,3-thiazol-5-ylmethyl)pyrido[1,2-a]pyrimidin-5-ium-4-one Chemical class O=C1N2C=CC=CC2=[N+](CC=2SC=NC=2)C(O)=C1C1=CC=C(F)C=C1 PXLXAWRVAPTDFO-UHFFFAOYSA-O 0.000 claims description 2
- SDRXGMVTMGLVCQ-UHFFFAOYSA-O 3-(4-fluorophenyl)-2-hydroxy-1-[(1-methylpyrazol-4-yl)methyl]pyrido[1,2-a]pyrimidin-5-ium-4-one Chemical class C1=NN(C)C=C1C[N+]1=C2C=CC=CN2C(=O)C(C=2C=CC(F)=CC=2)=C1O SDRXGMVTMGLVCQ-UHFFFAOYSA-O 0.000 claims description 2
- NPBQKDOXFICOPN-UHFFFAOYSA-O 3-(4-fluorophenyl)-2-hydroxy-1-[(2-methyl-1,3-thiazol-5-yl)methyl]pyrido[1,2-a]pyrimidin-5-ium-4-one Chemical class S1C(C)=NC=C1C[N+]1=C2C=CC=CN2C(=O)C(C=2C=CC(F)=CC=2)=C1O NPBQKDOXFICOPN-UHFFFAOYSA-O 0.000 claims description 2
- LWTQAFOMJHWZJG-UHFFFAOYSA-O 3-(5-chloro-2-fluorophenyl)-1-[(2-chloro-1,3-thiazol-5-yl)methyl]-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical class O=C1N2C=CC=CC2=[N+](CC=2SC(Cl)=NC=2)C(O)=C1C1=CC(Cl)=CC=C1F LWTQAFOMJHWZJG-UHFFFAOYSA-O 0.000 claims description 2
- VLBLSCYXSVQECH-UHFFFAOYSA-O 3-[(6-chloropyridin-3-yl)methyl]-5-(4-fluorophenyl)-6-hydroxy-1,2-dimethylpyrimidin-1-ium-4-one Chemical class OC1=C(C=2C=CC(F)=CC=2)C(=O)[N+](C)=C(C)N1CC1=CC=C(Cl)N=C1 VLBLSCYXSVQECH-UHFFFAOYSA-O 0.000 claims description 2
- PEXALFOPMHIWPM-UHFFFAOYSA-O 3-[3-(6-chloropyridin-3-yl)phenyl]-1-[(2-chloro-1,3-thiazol-5-yl)methyl]-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound O=C1N2C=CC=CC2=[N+](CC=2SC(Cl)=NC=2)C(O)=C1C(C=1)=CC=CC=1C1=CC=C(Cl)N=C1 PEXALFOPMHIWPM-UHFFFAOYSA-O 0.000 claims description 2
- WWDLSCBXVBTTDD-UHFFFAOYSA-O 3-fluoro-4-[1-[(6-fluoropyridin-3-yl)methyl]-2-hydroxy-4-oxopyrido[1,2-a]pyrimidin-5-ium-3-yl]benzonitrile Chemical class O=C1N2C=CC=CC2=[N+](CC=2C=NC(F)=CC=2)C(O)=C1C1=CC=C(C#N)C=C1F WWDLSCBXVBTTDD-UHFFFAOYSA-O 0.000 claims description 2
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- 239000004548 suspo-emulsion Substances 0.000 description 1
- 239000000271 synthetic detergent Substances 0.000 description 1
- ORUGTGTZBRUQIT-UHFFFAOYSA-N tert-butyl n-pyridin-2-ylcarbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=CC=N1 ORUGTGTZBRUQIT-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
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- 239000002562 thickening agent Substances 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
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- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
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- 108700012359 toxins Proteins 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000005945 translocation Effects 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 description 1
- ZDRNMODJXFOYMN-UHFFFAOYSA-N tridecyl acetate Chemical compound CCCCCCCCCCCCCOC(C)=O ZDRNMODJXFOYMN-UHFFFAOYSA-N 0.000 description 1
- MCVUKOYZUCWLQQ-UHFFFAOYSA-N tridecylbenzene Chemical class CCCCCCCCCCCCCC1=CC=CC=C1 MCVUKOYZUCWLQQ-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 238000004235 valence bond calculation Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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- 239000000080 wetting agent Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/14—Ectoparasiticides, e.g. scabicides
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Tropical Medicine & Parasitology (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
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| US4342808P | 2008-04-09 | 2008-04-09 | |
| US43428P | 2008-04-09 | ||
| PCT/US2009/032584 WO2009099929A1 (en) | 2008-02-06 | 2009-01-30 | Mesoionic pesticides |
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| ES2416083T3 true ES2416083T3 (es) | 2013-07-30 |
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| AU2014201144B2 (en) * | 2008-02-06 | 2015-07-16 | Fmc Corporation | Mesoionic pesticides |
| TWI468407B (zh) * | 2008-02-06 | 2015-01-11 | Du Pont | 中離子農藥 |
| MX2011004133A (es) | 2008-10-30 | 2011-05-24 | Hoffmann La Roche | Derivados de arilpiridona antiviral heterociclica. |
| SG172778A1 (en) * | 2008-12-22 | 2011-08-29 | Hoffmann La Roche | Heterocyclic antiviral compounds |
| UA107804C2 (en) | 2009-08-05 | 2015-02-25 | Du Pont | Mixtures of pesticides mezoionnyh |
| IN2012DN00838A (enExample) * | 2009-08-05 | 2015-06-26 | Du Pont | |
| AU2010279574A1 (en) * | 2009-08-05 | 2012-02-09 | E. I. Du Pont De Nemours And Company | Mesoionic pesticides |
| UA110924C2 (uk) | 2009-08-05 | 2016-03-10 | Е. І. Дю Пон Де Немур Енд Компані | Мезоіонні пестициди |
| BR112012005200A2 (pt) * | 2009-09-09 | 2021-02-02 | E.I. Du Pont De Nemours And Company | compostos, mistura herbicida, composições herbicidas e método para controlar o crescimento de vegetação indesejada |
| BR112012027283A2 (pt) * | 2010-04-27 | 2015-09-15 | Syngenta Participations Ag | método de controle de afídeos resistentes a neonicotinoides |
| JP2012149043A (ja) * | 2010-12-27 | 2012-08-09 | Sumitomo Chemical Co Ltd | 有害節足動物防除組成物及び有害節足動物の防除方法 |
| WO2012090516A1 (en) * | 2010-12-27 | 2012-07-05 | Sumitomo Chemical Company, Limited | Arthropod pest control composition and method for controlling arthropod pests |
| WO2012090515A1 (en) * | 2010-12-27 | 2012-07-05 | Sumitomo Chemical Company, Limited | Arthropod pest control composition and method for controlling arthropod pests |
| EP2658380A4 (en) * | 2010-12-27 | 2014-05-28 | Sumitomo Chemical Co | ARTHROPODENIC COMBUSTION COMPOSITION AND ARTHROPODENE COMBUSTION PROCESS |
| TWI528899B (zh) * | 2010-12-29 | 2016-04-11 | 杜邦股份有限公司 | 中離子性殺蟲劑 |
| WO2012106495A1 (en) | 2011-02-03 | 2012-08-09 | E. I. Du Pont De Nemours And Company | Mesoionic pesticides |
| WO2012136724A1 (en) | 2011-04-06 | 2012-10-11 | Basf Se | Substituted pyrimidinium compounds for combating animal pests |
| WO2012154533A2 (en) * | 2011-05-06 | 2012-11-15 | Dow Agrosciences Llc | Controlling planthoppers |
| AR086286A1 (es) * | 2011-05-06 | 2013-12-04 | Dow Agrosciences Llc | Control de los insectos saltadores de plantas |
| CN102246774B (zh) * | 2011-05-17 | 2013-05-15 | 德强生物股份有限公司 | 一种包含杀虫环的杀虫增效组合物 |
| TWI572587B (zh) | 2011-12-15 | 2017-03-01 | 杜邦股份有限公司 | 丙二酸二鹽及用以製備丙二醯基二鹵化物之方法 |
| WO2013144228A1 (en) | 2012-03-29 | 2013-10-03 | Basf Se | Pesticidal methods using heterocyclic compounds and derivatives for combating animal pests |
| AU2013277462B2 (en) * | 2012-06-21 | 2017-06-29 | Fmc Corporation | Solid forms of a pyrido-pyrimidinium inner salt |
| JP6119362B2 (ja) * | 2012-06-21 | 2017-04-26 | 住友化学株式会社 | 有害節足動物防除組成物及び有害節足動物の防除方法 |
| JP2017141250A (ja) * | 2012-06-21 | 2017-08-17 | 住友化学株式会社 | 有害節足動物防除組成物及び有害節足動物の防除方法 |
| JP2014024830A (ja) * | 2012-06-21 | 2014-02-06 | Sumitomo Chemical Co Ltd | ウンカ類の防除方法 |
| RU2503666C1 (ru) * | 2012-06-25 | 2014-01-10 | Открытое акционерное общество "Государственный научно-исследовательский институт "Кристалл" (ОАО "ГосНИИ "Кристалл") | Способ получения 2-метилпиримидин-4,6-(3н, 5н)-диона |
| WO2014005982A1 (de) | 2012-07-05 | 2014-01-09 | Bayer Cropscience Ag | Insektizide und fungizide wirkstoffkombinationen |
| EP2684879A1 (en) | 2012-07-09 | 2014-01-15 | Basf Se | Substituted mesoionic compounds for combating animal pests |
| PL2931716T3 (pl) | 2012-12-13 | 2017-04-28 | Novartis Ag | Pochodne pirydonu i ich zastosowanie w leczeniu gruźlicy |
| AR096022A1 (es) * | 2013-04-11 | 2015-12-02 | Basf Se | Compuestos de pirimidinio sustituido, útiles para combatir plagas de animales |
| WO2014202582A1 (en) * | 2013-06-17 | 2014-12-24 | Basf Se | Substituted pyrimidinium compounds and derivatives for combating animal pests |
| WO2015055554A1 (de) | 2013-10-14 | 2015-04-23 | Bayer Cropscience Ag | Wirkstoff für die saatgut- und bodenbehandlung |
| UY35772A (es) | 2013-10-14 | 2015-05-29 | Bayer Cropscience Ag | Nuevos compuestos plaguicidas |
| WO2015059088A1 (de) | 2013-10-23 | 2015-04-30 | Bayer Cropscience Ag | Substituierte chinoxalin-derivate als schädlingsbekämpfungsmittel |
| US10273226B2 (en) | 2014-01-03 | 2019-04-30 | Bayer Animal Health Gmbh | Pyrazolyl-heteroarylamides as pesticides |
| AR099120A1 (es) | 2014-01-20 | 2016-06-29 | Bayer Cropscience Ag | Derivados de quinolina como insecticidas y acaricidas |
| ES2819505T3 (es) | 2014-04-02 | 2021-04-16 | Bayer Cropscience Ag | Derivados de N-(1-(hetero)aril-1H-pirazol-4-il)-(hetero)arilamida y su uso como pesticidas |
| EP3139743B1 (en) | 2014-05-08 | 2018-03-14 | Bayer CropScience Aktiengesellschaft | Pyrazolopyridine sulfonamides as nematicides |
| CN106715424B (zh) | 2014-06-05 | 2020-07-14 | 拜耳作物科学股份公司 | 作为农药的双环化合物 |
| WO2016001119A1 (de) | 2014-07-01 | 2016-01-07 | Bayer Cropscience Aktiengesellschaft | Insektizide und fungizide wirkstoffkombinationen |
| CN104082333A (zh) * | 2014-07-03 | 2014-10-08 | 广西农喜作物科学有限公司 | 含噻虫胺的杀虫组合物 |
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| US10149477B2 (en) | 2014-10-06 | 2018-12-11 | Basf Se | Substituted pyrimidinium compounds for combating animal pests |
| WO2016055096A1 (en) | 2014-10-07 | 2016-04-14 | Bayer Cropscience Ag | Method for treating rice seed |
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| EP3081085A1 (en) | 2015-04-14 | 2016-10-19 | Bayer CropScience AG | Method for improving earliness in cotton |
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| IN2012DN00838A (enExample) | 2009-08-05 | 2015-06-26 | Du Pont | |
| UA110924C2 (uk) | 2009-08-05 | 2016-03-10 | Е. І. Дю Пон Де Немур Енд Компані | Мезоіонні пестициди |
| UA107804C2 (en) | 2009-08-05 | 2015-02-25 | Du Pont | Mixtures of pesticides mezoionnyh |
| AU2010279574A1 (en) | 2009-08-05 | 2012-02-09 | E. I. Du Pont De Nemours And Company | Mesoionic pesticides |
| TWI528899B (zh) | 2010-12-29 | 2016-04-11 | 杜邦股份有限公司 | 中離子性殺蟲劑 |
| WO2012106495A1 (en) | 2011-02-03 | 2012-08-09 | E. I. Du Pont De Nemours And Company | Mesoionic pesticides |
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