ZA200101399B - Thiazolylcinnamonitriles and pest controlling agents. - Google Patents
Thiazolylcinnamonitriles and pest controlling agents. Download PDFInfo
- Publication number
- ZA200101399B ZA200101399B ZA200101399A ZA200101399A ZA200101399B ZA 200101399 B ZA200101399 B ZA 200101399B ZA 200101399 A ZA200101399 A ZA 200101399A ZA 200101399 A ZA200101399 A ZA 200101399A ZA 200101399 B ZA200101399 B ZA 200101399B
- Authority
- ZA
- South Africa
- Prior art keywords
- optionally substituted
- alkyl
- ome
- compounds
- alkoxy
- Prior art date
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- 241000607479 Yersinia pestis Species 0.000 title claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 57
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 13
- 239000004480 active ingredient Substances 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 125000001188 haloalkyl group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 1
- -1 dibromomethyl Chemical group 0.000 description 59
- 239000000460 chlorine Substances 0.000 description 26
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 24
- 241000238631 Hexapoda Species 0.000 description 17
- 125000001424 substituent group Chemical group 0.000 description 16
- 230000000895 acaricidal effect Effects 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000000642 acaricide Substances 0.000 description 12
- 239000002917 insecticide Substances 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 230000001276 controlling effect Effects 0.000 description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 239000004495 emulsifiable concentrate Substances 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 241000238876 Acari Species 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 4
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 4
- 230000009969 flowable effect Effects 0.000 description 4
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 4
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- 239000004563 wettable powder Substances 0.000 description 4
- ZWKNLRXFUTWSOY-QPJJXVBHSA-N (e)-3-phenylprop-2-enenitrile Chemical class N#C\C=C\C1=CC=CC=C1 ZWKNLRXFUTWSOY-QPJJXVBHSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 241001600408 Aphis gossypii Species 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000003905 agrochemical Substances 0.000 description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 125000005997 bromomethyl group Chemical group 0.000 description 3
- 239000000073 carbamate insecticide Substances 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000417 fungicide Substances 0.000 description 3
- IXORZMNAPKEEDV-OBDJNFEBSA-N gibberellin A3 Chemical class C([C@@]1(O)C(=C)C[C@@]2(C1)[C@H]1C(O)=O)C[C@H]2[C@]2(C=C[C@@H]3O)[C@H]1[C@]3(C)C(=O)O2 IXORZMNAPKEEDV-OBDJNFEBSA-N 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- 125000006000 trichloroethyl group Chemical group 0.000 description 3
- XERJKGMBORTKEO-VZUCSPMQSA-N (1e)-2-(ethylcarbamoylamino)-n-methoxy-2-oxoethanimidoyl cyanide Chemical compound CCNC(=O)NC(=O)C(\C#N)=N\OC XERJKGMBORTKEO-VZUCSPMQSA-N 0.000 description 2
- NFTOEHBFQROATQ-UHFFFAOYSA-N 2,3-dihydrofuran-5-carboxylic acid Chemical compound OC(=O)C1=CCCO1 NFTOEHBFQROATQ-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 241000251468 Actinopterygii Species 0.000 description 2
- 241001124076 Aphididae Species 0.000 description 2
- 241001184747 Caloptilia theivora Species 0.000 description 2
- 240000008067 Cucumis sativus Species 0.000 description 2
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 2
- 239000005756 Cymoxanil Substances 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000409991 Mythimna separata Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 241000255588 Tephritidae Species 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 239000002519 antifouling agent Substances 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
- 238000009835 boiling Methods 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 230000003292 diminished effect Effects 0.000 description 2
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- 239000003480 eluent Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- SEEGHKWOBVVBTQ-NFMPGMCNSA-N gibberellin A7 Chemical compound C([C@@H]1C[C@]2(CC1=C)[C@H]1C(O)=O)C[C@H]2[C@]2(C=C[C@@H]3O)[C@H]1[C@]3(C)C(=O)O2 SEEGHKWOBVVBTQ-NFMPGMCNSA-N 0.000 description 2
- RONFGUROBZGJKP-UHFFFAOYSA-N iminoctadine Chemical compound NC(N)=NCCCCCCCCNCCCCCCCCN=C(N)N RONFGUROBZGJKP-UHFFFAOYSA-N 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- IXJOSTZEBSTPAG-UHFFFAOYSA-N methasulfocarb Chemical compound CNC(=O)SC1=CC=C(OS(C)(=O)=O)C=C1 IXJOSTZEBSTPAG-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 229960000321 oxolinic acid Drugs 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 239000005648 plant growth regulator Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002728 pyrethroid Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229960001866 silicon dioxide Drugs 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000004546 suspension concentrate Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- ZCVAOQKBXKSDMS-AQYZNVCMSA-N (+)-trans-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-AQYZNVCMSA-N 0.000 description 1
- CXBMCYHAMVGWJQ-CABCVRRESA-N (1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)methyl (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCN1C(=O)C(CCCC2)=C2C1=O CXBMCYHAMVGWJQ-CABCVRRESA-N 0.000 description 1
- SBNFWQZLDJGRLK-RTWAWAEBSA-N (1R)-trans-phenothrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 SBNFWQZLDJGRLK-RTWAWAEBSA-N 0.000 description 1
- FHNKBSDJERHDHZ-UHFFFAOYSA-N (2,4-dimethylphenyl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OCC1=CC=C(C)C=C1C FHNKBSDJERHDHZ-UHFFFAOYSA-N 0.000 description 1
- WXBHKHTWAPLUSQ-UHFFFAOYSA-N (2-methyl-5-prop-2-ynylfuran-3-yl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OCC1=C(C)OC(CC#C)=C1 WXBHKHTWAPLUSQ-UHFFFAOYSA-N 0.000 description 1
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- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Lone $7
SPECIFICATION
THIAZOLYLCINNAMONITRILES AND PEST CONTROLLING AGENTS
The present invention relates to novel thiazolylcinnamonitriles and pest controlling agents containing the said compounds as active ingredients.
A large number of pest controlling agents, such as insecticides and acaricides, have been used so far. However, many of them are hardly satisfactory as controlling agents because of insufficient efficacy, restrictions on their use due to drug resistance problems, phytotoxicity or pollution on plants, or strong toxicity on humans, domestic animals and fish. Therefore, there bas been a desire for the development of agents applicable safely and having less of the drawbacks mentioned above.
As for cinnamonitrile derivatives similar to the compounds of the present invention, for example, 3-hydroxy-2-(4-phenyl-2-thiazolyl)-cinnamonitriles are disclosed in Japanese Patent Laid- open No. Sho 53-92769, Japanese Patent Laid-open No. Sho 55-154963 and EP 189960, and their alkali metal and ammonium salts in Japanese Patent Laid-open No. Sho 55-154962. However, none of them has been put to practical use as insecticides because of insufficient efficacy and other problems.
Further, WO 95/29591 and Japanese Patent Laid-open No. Hei 10-158254 have disclosed cinnamonitrile derivatives, similar to the compounds of the present invention, that are useful as anti- fouling agents for aquatic adhesive organisms. There are, however, no descriptions on their insecticidal activities.
It is an object of the present invention to provide pest controlling agents containing thiazolylcinnamonitriles as active ingredients, that have sure efficacy and can be used safely.
The present invention is directed to compounds represented by Formula (1) \ ot / ~
N \_/ (1) [wherein A is halogen, C, alkyl, C,¢ haloalkyl, C, 4 alkoxy, optionally substituted C; 5 cycloalkyl, optionally substituted pyridyl, optionally substituted thienyl, substituted phenyl or optionally substituted phenoxy;
B is hydrogen, halogen, C, 4 alkoxycarbonyl, optionally substituted phenyl, C alkyl, Cy haloalkyl or C; 4 cycloalkyl; .
Ris C,4alkyl, a group of Formula COR! (wherein R! is C,_, alkyl, C, 4 haloalkyl, optionally substituted C; 4 cycloalkyl, C, ¢ alkoxy, C4 alkoxy C, 4 alkyl, C, alkylthio C, alkyl, mono-C, 4 alkylamino, di-C, ¢ alkylamino, optionally substituted phenyl C, 4 alkyl, optionally substituted phenoxy C, alkyl, optionally substituted phenylthio C, alkyl or optionally substituted phenyl), or a group of Formula SO,R? (wherein R? is C, 4 alkyl or optionally substituted phenyl);
X is cyano, nitro, halogen, C, 4 alkyl, C, 4 haloalkyl, C4 alkoxy, C, haloalkoxy, optionally substituted phenyl or optionally substituted phenoxy; and n is an integer between 1 and 5], and pest controlling agents containing one or more of the said compounds as active ingredients.
In the above Formula (1),
A is halogen such as fluorine, chlorine, bromine and iodine;
Cs alkyl such as methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, t-butyl, pentyl and its isomers, and hexyl and its isomers;
C,. haloalkyl such as chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tribromomethyl, trichloroethyl, trifluoroethyl and pentafluoroethyl,
C,. alkoxy such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy and t-butoxy; optionally substituted C, ¢ cycloalkyl such as cyclopropyl, cyclopentyl, 1-methylcyclopentyl, cyclohexyl and 1-methylcyclohexyl; optionally substituted pyridyl, such as 2-pyridyl, 3-pyridyl and 4-pyridyl that may have substituents at arbitrary positions of the pyridine ring; thienyl, such as 2- thienyl and 3- thienyl I that may have substituents at arbitrary positions of the thiophene ring; phenyl having substituents at arbitrary positions of the benzene ring; or phenoxy having optional substituents at arbitrary positions of the benzene ring.
Examples of substituents of the aforementioned pyridyl, thienyl, phenyl and phenoxy groups include halogens such as fluorine and chlorine; C, 4 alkyl such as methyl and ethyl; C, 4 alkoxy such as methoxy, ethoxy and isopropoxy; and nitro. These pyridyl, thienyl, phenyl and phenoxy groups may have two or more, same or different, substituents.
B is hydrogen; halogen such as fluorine, chlorine, bromine and iodine;
Cs alkoxycarbonyl such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl and t-butoxycarbonyl;
Cs alkyl such as methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, t-butyl, pentyl and hexyl;
Cs haloalkyl such as chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tribromomethyl, trichloroethyl, triflucroethyl and pentafluoroethyl; or
C,¢ cycloalkyl such as cyclopropyl, cyclopentyl and cyclohexyl.
R is C, 4 alkyl such as methyl, ethyl, propyl, isopropyl, butyl! and t-butyl; or a group represented by Formula COR! or SO,R?, wherein R' is C,.;, alkyl such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl, t-
butyl, pentyl and its isomers, hexyl and its isomers, heptyl and its isomers, nonyl and its isomers and dodecyl, and branched alkyl groups are particularly preferred;
C, haloalkyl such as chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tribromomethyl, trichloroethyl, trifluoroethyl and pentafluoroethyl; optionally substituted C, 4 cycloalkyl such as cyclopropyl, 1-methylcyclopropyl, cyclopentyl, 1-methylcyclopentyl, cyclohexyl and 1-methylcyclohexyl;
Cs alkoxy C, alkyl such as methoxymethyl, methoxyethyl, ethoxymethyl, propoxymethyl and butoxymethyl;
C5 alkylthio C, alkyl such as methylthiomethyl, methylthioethyl, ethylthioethy], ethylthiomethyl, propylthiomethyl and butylthiomethyl, mono- or di-C, 4 alkylamino such as methylamino, ethylamino, propylamino, dimethylamino, diethylamino, dipropylamino, dibutylamino and ethylisopropylamino; optionally substituted phenyl C,¢ alkyl, such as benzyl, phenethyl and phenylpropyl that may have substituents at arbitrary positions of the benzene ring; optionally substituted phenoxy C, alkyl, such as phenoxymethyl and phenoxyethyl that may have substituents at arbitrary positions of the benzene ring; optionally substituted phenylthio C, alkyl, such as phenylthiomethyl, phenylthioethyl, phenylthiopropyl and phenylthiobutyl that may have substituents at arbitrary positions of the benzene ring; or phenyl having optional substituents at arbitrary positions of the benzene ring.
R? is C, 4 alkyl such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl, t-butyl, pentyl and its isomers, and hexyl and its isomers, or phenyl having optional substituents at arbitrary positions of the benzene ring.
In these R! and R?, examples of benzene-ring substituents of the phenyl C4 alkyl, phenylthio
C,, alkyl, phenoxy C, alkyl and phenyl groups include halogen such as fluorine and chlorine, C4 alkyl such as methyl and ethyl, C, 4 alkoxy such as methoxy, ethoxy and isopropoxy, and nitro.
These benzene rings may have two or more, same or different, substituents.
X is cyano, nitro, halogen such as chlorine, bromine and fluorine;
C,. alkyl such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl, t-butyl, pentyl and its isomers, and hexyl and its isomers;
C. haloalky! such as chloromethyl, fluoromethyl, dichloromethyl, trichloromethyl, trifluoromethyl, 1-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl and pentafluoroethyl,
C, alkoxy such as methoxy, ethoxy, propoxy, isopropoxy and butoxy;
C, haloalkoxy such as chloromethoxy, dichloromethoxy, trichloromethoxy, trifluoromethoxy, 1-fluoroethoxy and 1,1-difluoroethoxy; optionally substituted phenyl, or optionally substituted phenoxy.
Examples of substituents of these phenyl and phenoxy groups include halogen such as fluorine and chlorine; C, alkyl such as methyl and ethyl; C, alkoxy such as methoxy, ethoxy and isopropoxy; and nitro. The said phenyl group may have two or more, same or different, substituents. ~ When nis 2 or larger, X’s may be the same or different groups.
Compounds having particularly excellent pest controlling effects among the compounds of the present invention, compared to similar, known cinnamonitrile compounds, are those where, in the above Formula (1), A is C, 4 alkyl, optionally substituted C, ; cycloalkyl, optionally substituted pyridyl, optionally substituted thienyl or substituted phenyl; B is hydrogen; R is COR! or SO,R? and
X is halogen, C, alkyl, C,¢ haloalkyl or C,¢ alkoxy, and at least one of the substituents is at position 2,
Forms to Implement the Invention:
The compounds of the present invention are prepared, for example, according to the following:
B 7 H B R
Ds UO NRE a Sr (
N ( —Xn (RCO)0 Sats
CN N \
N
(2) %)) (wherein A, B, R, X and n are as defined above, and L! is a leaving group such as halogen, C, alkoxy, phenoxy, 1-imidazolyl, 1-pyrazolyl, p-toluenesulfonyloxy, methanesulfonyloxy or trifluoromethanesulfonyloxy).
That is, 1 mole of a compound of Formula (2) is reacted with 0.5 to 2 moles of a compound of
Formula (3) in an inert solvent in the presence of a base, to give a compound of Formula (1).
Examples of bases used for this reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; carbonates such as sodium carbonate and potassium carbonate; organic metals such as n-butyl lithium and lithium diisopropylamide (LDA); and organic bases such as triethylamine, diisopropylethylamine and pyridine.
Solvents able to be used include N,N-dimethylformamide (DMF), dimethylsulfoxide (DMSO), tetrahydrofuran (THF), acetonitrile, hexamethylphosphoramide (HMPT), benzene, toluene, dichloromethane, chloroform and carbon tetrachloride. Preferred reaction temperatures are from - 78°C to the boiling point of solvents used.
The compounds of Formula (1) of the present invention have 2 stereoisomers. One of the isomers or a mixture of the isomers may be produced, depending on reaction conditions and purification methods. These isomers are all covered by the present invention.
A compound of Formula (2) of a starting material can be prepared as follows:
B H
De , i coL? ANE 4 x PCH XY / ~(
N
(4) 6 2) (wherein A, B, X and n are as defined above, and 1.2 is a leaving group such as halogen, C, 4 alkoxy, phenoxy, 1-imidazolyl or 1-pyrazolyl).
That is, 1 mole of a compound of Formula (4) is reacted with 0.5 to 2 moles of a compound of
Formula (5) in an inert solvent in the presence of a base, to give a compound of Formula (2).
Examples of bases used for this reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; carbonates such as sodium carbonate and potassium carbonate; organic metals such as n-butyl lithium and LDA; and organic bases such as triethylamine, diisopropylethylamine and pyridine.
Solvents able to be used include DMF, DMSO, THF, acetonitrile, hexamethylphosphoramide (HMPT), benzene, toluene, dichloromethane, chloroform and carbon tetrachloride. Preferred reaction temperatures are from -78°C to the boiling point of solvents used.
A target compound is obtained with usual post-treatments after the completion of the reaction.
The structures of the compounds of the present invention were determined by IR, MNR, MS and other means.
Representative examples of the compounds of the present invention, that can be prepared according to the above processes, are shown in Tables 1 to 4. The symbols used in the tables have the following meanings:
Me: methyl, Et: ethyl, Pr: propyl, Bu: butyl, Pen: pentyl, Hex: hexyl, Ph: phenyl, n: normal, i: iso, t: tertiary, neo: neo, and c: cyclo
0 o 0 0 . . nPr B
Ri: SE! Re: Ra; oc TS ii
Me Me Me Me Me Me Me” “Me ey A i A nHex CH,FPh CH,CF
RS: Ré: R7: CH,CHPh oo. H,CFy
Me Me Me Me “Ct Me Me 0
CH,CH,F CH,CH,CI H
Ro: Ae 2 1 LA HCH, CH,CH,OMe A ve Me R10: Xe Ar Cr R12: “nCHH,, x le) 0 10]
R13: CH.OMe R14: A criopn R15: A crisme R16: Arsen
Q 1 0 0
R17: “CH, ph R18: CH,CH,Ph ATg: Me a
Me Me 0 0 Me Me 0) (o}
Et Me 21.9 . AN i Et R22. Me R23: HAE R24: Nv 0 0 0
Me Me
R2s: “x R26: R27: “A R28: 20
E 0 Me
Rog: Me R30: R31: oO CC mY
F a NY R34: Ras: R36: —5~ Me cl Me Me 0)
Tablel1
Wa OR X, CFs oR X CS OR X,
F Nx; F NC x; # Ne NC x;
Crs X a oR X, "ors OR X
C0 ORS a ci Nx; a MC x; F NC x. rs OR X, Cs OR X, Fors OR X,
Sure ciisars clilsarss
Tone Mx Fo¥x a Mx
OMe _s oR x, PMe _s om x, Me _c Or X
Fo Nox a Noy, ome NC.
Crs Pr Cre f° 8 RX
NC NC
F Xi F x; NC x;
FL TS OR X, a OR X, Crs X,
SRL SN SOR
Ss OR X, S OR X, we 7S OR X, a0 TS RSS "x "x x rs RX rs X, rs x,
OA Oxy 0 a x; "x; Nx; $ Xs § OR X, S OR X :
Me | N J N "x; F NC x (o] NC x; [ YN me Nox,
[7S Rx gs or Xs OR x,
SOS BRS dy gp NC NC SR
X X KE x ¢ rs OR X, rs oR X, rs oR X, (o] x C1 NC E NC x Xx, x rs OR X, Fo rs x, & rs OR X, me NC F NC a
X, x, X, 0 7s OR X os oR X, oe rs OR X,
Cy Obey hy
Fo a ome NC xX x x ve or x, g — . Yo os oR x,
NG NC NC
F X, F X, x
F CFs OR X, 7s oR X, CFs OR X,
Yr Ay Ay = NC { JF NC [2 NC x x %
S OR X, Me S OR X Me Ss OR X, ree Tr TYro
NC = NC nPr NC x, X x § OR X s x s OR X,
Oy Orley Ay
NC Me NG % X, x
OP \ WV BPP N BOP
Me™ { N [ N
NC E NC - NC x x %
S X, {0} ’
Saree
Me NC 2 x
Br 5s om x cr . res: (AAR 0 > y 0
Cr oe race
F X X, om ox s
Me OR
CE Saree
PP } \
NC cl
X, X,
Of —s om Xx
CFs
OAS ERA Salsae
PP } \
Me NC f 7 s : r | OMe _s om x i» y SP ' [ILE NON
NC 7 OMe
Fo Ne cl { if
X,
Me —s or X { F
NN N hn
F 5
F x,
LG s X, a s OR X Cri x >
TAS oA Nats
NC Fl NC f / " Ss OR X
OR Me s X, myo 3 x, well 3.
Ay Sas Pr ne
YO ; : . xX FS OR X,
OR es [39% [3 ~ 0 “0 ; X,
X, X, i. s
OR
Ody ro N hy 3
Me =, "ud ; * X, s OR X,
I Yr °N 0
X,
F J
3. X, cl rs OR X, Br s x
OQ "d Salsas AANA
F X, [3 NC ¥
X, Fo Ne X, 8 rs x Me [3 rs RX Me 5 OR x cl NC xX, a x, F NC X,
Me rs OR X, CF, S CF.
Ay [3 x rs HX
NC N NY
Me x, F NC %, [o2] NC x,
OMe —s OR x OMe
Fi LI rs 5 PMe —s om x
N OL AAA
F N pi
X, a MN x, ome © %
Me
S$ OR X, a
SEAL GEE las ) NC x, NC TOL
F %2 Ne X cl
F 5 OR Me
POO EE FS RX f —s om x
N oS NN Xn PP
NC Ay NC Ly F OL s = ) 2 % is OR X, S OR * x, Fn AE 5)
X, ne X rs OR X, s X, $
NC Me N % X i X s OR
ALIEN BE CO
- Cert Cee x § X, ve NC X,
F FS oR X, Ci S OR X, Cs OR X,
F NC X, E NC X, F NC X, cl FS OR X, rs oR X, Me 7S x, a x a NC x FN x rs OR X, VE OR X, a OR X,
Me NC xX, F NC X, Cl NC X, os OR X, os oR X, hes x,
CN Cr ey £ NC X, a NC x, : ome NC X,
Yrs ox 2 rs RX ce Ms on x ) NC x) NC x n ‘
For mS OR Xo rs OR X, ct SR OX
Uy x Oy AAA g RAT ne x NC Ny 8 RX S OR X, Me /~S OR X%
NC X, & NC X, nPr NC x, 78 ®F $ OR % FS RX
Ne X, NC ’ X, NC X,
I» IN N 3 B® % = EL ne X, Fo X, a X, s OR we NC Ah
( 75 In C Fs RX LP § OR X
F NC 3 NC E NC {rs $x rs Rx Yo rs om x
Sara Serass Oe ey
Ci NC Cl NC E NC rs OR X, Crs OR X, a OR X, a NC F NC a NC 7s oR Xx ors OR X, rs X,
Fo a © ome 1
Me s OR X, [~ s X, Me { / F § OR X
NC NC "
F F . rl 8 OR X, ers or x, os oR x,
A 7 Are Ady x, Ay x, = NC 2 F NC F NC 3 FF Me /~S OR X Me SOR X, sd A x wll A NX wed A X,
NC a NC > nPr NC 7s X, FS OR X, FS X,
OA ye xl Orley X, NAA X,
NC _ Me NC NC § OR X § OR X, s X,
Ae 2 Oley X, Clery X,
Me™ lL _ = "x =, § OR X,
Cor Gs
CO Me NC Z
F
$ oR X cl Ss OR Br = » J Xe s OR X, .
F g NC FNC 5 a -
Sy, Urs gx Ye rs ox, : (o} a NM E NC ER
Me —s om x, CF, cE 2 /] bP x J Ss OR X, 3 / S X, 5
Me FNC a =
J hb _ xX OMe fj Ss OR X, OMe f $ OR X, &
Foe a ome NC 5
Ss OR :
Bs L050, rte pe
N 2] N = X, & PP X,
NC NC YOY :
F [3 } NC
Cl « Me 3 [3 S OR X, S OR ct : 7 : x Ss R :
NC 2 F\= NC F N NC A
S OR X, Me s oR X, s R =
NC E NC nPr NC 3 3
Me N x a
NC NG we = » IN NOS RX $s OR X g.
FNC Ny NC : sS OR X .
Ce >. X, 3
Xx J% ir Os E x, x [E a a cl a
SE ll cl a LC ch Lc
Kc 0 CY cc Cc
Rc Cc Lc
Re cc a a i cc
Le 8 a on
CF, | Hd | COnBu CF TH | R30 Me TH [8 Me TH | SO.nPr
SE Fc a a
Si Fl GO ci
Ki Gc i cm i cc a a ca
Ko A GC OO cE cl a cai
Ra cl cl ci
Ra i cc cl lL cc [CF 1H | R8 CF IH {Somer [Ne PH Tris al E | COCF,
CF. | H | R9 JCF iH ! SOuiPx Me 1H | B19 IE {Hj COMe
CFs H R10 [CF HRT Me | H | R20 E H | COnBu
Ko ES cL LO cic
Ra A EG cc a al ca
Ee ec lO LC
Jc cc ch IN
Ba cc LCI LS
CFs H | R18 [Me iH COCE {Me IH | R28 {a 1H | BS
BC CO cc cL Rc al La LA
Table 1 (continued) }
ENN
SC 0 i
SY cc Lc ic
SY ec ec el ial 0 cc cil cl
CN Ll Ll Ln eo Ln Le LL a cc ic a
Sc a ic a
Tw
GG cc Lc LS il
GR oc A GO cl
Se 0 cd Le OO ca
Sal a a ca A
ELL Cl Li EE a A cal
NL ORL Eo Le
LL
CG |H [Rm Br PHO[RT TE |H SOE [OMe [H |COMs a 0 cL cc ec il
FC cc cc LO ch
Fa CR i I 8
Fl LL cL cl I ic
FM A a Li A cal
Fc LA I Lc
Fl A CL co acc A a
Fc a A ca co a
Cl ro. e u
Fc a CO ca cl cl
Table 1 (continued) }
TT i LC CO A Lc a eC cc oc a
A cc) AN LN La
LA YA Lc a i La
A A OY a cc il Mc ec LL Ld
LCL = Lf on
A cc cL co
EE A ec A el Cc
SS ca cL ch cai
A ac cL cal cy i cH A Lai tec cA BB
A LL a cA al Kc
Cc GL lO
SE a a cc LA a cc
Lc cL a
SE Yc A a Bcc
EE A Ml ic
TT
EE ec i cL al cc
A Lc a cc A all
CD cc A a ac cc cc a
A A cL al A a I Lc cS LA GL
A cL cL LA aL
SE A a a ca A a
A a cB LA
Table 1 (continued) ] i EY LO LN LI cr ct Cara a
Rl A cl cl cl cal al lL Cc al Cl
Ec ec a cll
Re cl a Cl
Lc LO Ly La ll cl a cll al cia
Nl A a il cll cc le col Sc cl a le cc Fl Kl ca al Cc ca
Bec i i re fear fr — lc cB ci ll LL al lc cl Ll lL i cc al a a ec cl
A le a i le lc Kc LL lc a cl La ll cl Oc a La ; EC I Cc refer
A el Fc cl Ll
ML oc LN a a LO ce cll LO
Cl ca Kl Lc
Table 2 [| ~s or x / ' Y S OR (3; b ® B X, FS OR X ng n oy Na
X; Ne ; X;
Y FS RX Y Y
A BO 7S OR xX, hg AEA Sang
X; J x;
Y SR Xx Y Ss OR X
SP J 1 Y
NC Y
X Ne Y " y ) 5 ~ v SOR X y pe y FS. 9% N FS OR X, » N ZZ PN
J X; y MN Y "a x Y x; ) rs. FR % Y FS OR X y
NC Y ng
Y X; J NC x; Y TO v x; y y Ss OR X y
J : Y 3
A YS 1 \ AS Tras
Y NC ng x. ME NC. Y PSS vy 7 x:
YY] X R or i | CO:CH.Ph - H 3 - - H | CONMe. : Me 7X. R au FORE [Rm FT | [Me [F | Comvier 7 = E [Coda eT ; Me H
Foe Ga
TH COnPr i lk : i CF, i i H COnBu il : : (Fo [Me] EN |Re i COPh | : : y
CF, | i : : coccql, ¥ H ee : |i Jcock, | FE Re] : :
CF, |H : : — CF | [F[coMe | | CoM ee
C EK] rer Sas Saas
F; |H i C : ll | : oo, I CO.CH,Ph CF, [H | Me | - - ] : ! CF, | H i = : = i i H R1 =
F CF, i
LmCaim A a a Li
A a LA EE : 2 = 2 Tr = : — : H CH,Ph El EH R17
CONLIN Lo Ln i
RS
CF, | H : = = i i R19 a - S0.n Pr i i
F : H CF, |H = i : . = iw d i | SOPs TF 3 Me
F IH R8 i | - : i CF,
F ] H R9 "CF, H : =
I CF, i : stn: ANIL om Lo : I EEN [Me EN | R24
A
[RE [E eon ==
CF, | i : = ; : - | Me | |B | comp] OnPr = min | : RIS . 1 | ComBu | ] — - kak he Me i : = : COP | EB
F | : RIS | | : :
Me a i | [H] COCcCl, -
F | Th : :
Me : i R17
F - | R18 bi =
Ea | - CO,nBu — R19 :
CF, |H - i _ R20
CF, 'H
Fen iE [Re fF [Me TF (Cem [F [We [Fm
Table 2 (continued) oo
I A ON SC A EN ER
I EE Cl CE LR LR ER EE
I Ec EE CI
GL LO EA ER EE
Rc a CL a LO EC LN CE
I a Ll EC a
RI EE B [oor
EA a A Li a a
Cc a CC El a
Tc co
RE a SC CG EE
Ra i Li LL LL
Fue [HO JRs 2]
I cc EE a El
FF [eos] El LN EE
Fo |¥ [oom TFG TE [ms | ®
EL a Ln Lo mt
I ec A LO cL a a
EG I CO
LL Le am
I ec EC LE a
RI Ec LL EO
OR aC EO EI
LO A Cm A aL
ES GEN LN
Ca A a Lc
Ec CC Cl Ea LC nm cc A 0 a
Ia Kl EE EL EA
LO Le A LE a 8 i
Table 2 (continued) . 4 :
EE LL LN Lo EC EI 1
Ea EO a EO ea :
CC A a Ea cc LO LA eo ;
CT a cc LL EA : a ec EE Ca 7 ec a a ca : a A a a a : a ccc ll A ea :
FE Le mn LA LA ccm : a 4
LA Ea En a LO AL cc i a I ea A Le :
I CL co a a A :
I EC Cc ccc La A CL cs Ea LL
CC a cl LL LO LI :
I Oc cc a A LS : a CL A a a a a :
A I LL LI La LL 1 a i a ct a LC
I ccc a LL 3 a a cE cc Ea LL Lc 3
Cc Fo cc a LA 2 cc Lo LL 1
LO La LL a a A LA A 2
CO cc a ca Sa A cy cc EA z
Cc cc A LE :
SG cL Rc Ll a LI 1
Table 2 (continued) a
A CR A EL EE EN
EG EY EE EC I
Ro a a i cL A
I CL EO I ER a
IS CE cL A
IG ec LL A
EG Cc GS LC I I CR a
I A FE LL LL cl EC LN CA a
FG LN CR I
EN CL LI LA
I Yc A cL LE EC
EC a EE LO I CR Ea
LE A EL LA Cm Lg a a
Fol GC EL a CL
EE LC LL a i La tL a
IG a CL GE
I CO LO
CE LA ec LA LO CE I LE
IG cc EL a El
LL LC
I a GE a a cca
A a cc Eo CL A ac LA ec A LA
I lc a EE LI EE ey
LO LE La A A LA i cic
IG a Ec a Le
Sl LE EC CA
EC Lo i oe nn
Rc
RE LL
I El Rc Ca a
H
Table 2 (continued) . i
CREF TEE EE] :
EC Co cc 0 a :
RE EE EC GG EN ER El eo :
Iu CL LL a a 2 EO
RN a ES LE a 2S EI : a EL Gd a EE aa :
Ta a a a :
RL LU Ln A :
CN a :
I Ea LL a
EE UN CRE RL
EE ES Ea Eh
EE Ne raat I
A EG LN LO Ee LR SE
RE cove
LE LO ERE Lom A :
FTE Fo [owen] :
Eo fe feof fr :
EG NY Gc cc hc a a lL :
EE a a EN EO :
ES Eo El EO :
I cE EN EO a Lo LN ec LN EN La
EE ER EE :
Table 2 (continued) oo
IN ON TG A EN EC
I
RE i cc Ec cl a a ec 3
Bl Ec Ec a a a
EY oc cl i a
Tl Cl i EL a LN
Rl cc Ec ec Ke ec
Ean 3 > [oF [7 [sor] Ral EN
Bl Gc cE a CE Le
Ri cc Ec cl a EO
EE
[C05 | Ea fre fe fff —
Bl tc cc Rc Ec LO
He Eee a NN EL a
El Cc cE cn Ee EO
Bl cl cL cl LA
CLR LL nL a EA oe [we I
Rl lO cl ES CE LC
Rl CO i CO Ee cl
Rel YF Ec Lc EO EX ol Ec Rc cc ec KE
Tl Fc Rc cc
Cc cc a a La
Rl a ec a
Table 2 (continued) . !
MEE A EE CE LN A EN ES
EE EE EN EO EE al a a CO I LE ER EO ES
Rl a ET Lh a el La EE
Tl ON KL i I lL Le a LL am La a LE EC ER Ee EN OE a a CE a a EN
EE LL Ca Le Ca a el A a EO lL EE ll SE EE a ER EE el i a a a La I al I El La a a ER EE
Kl I EE a EO a a a ey
Cm LA A al ON a a LN I A al a A a a I A al EL I) a a LA El
I Fc a a A CI al i EE a EN I
I I Ec a i a LL a
Tl Ec a Ea a Lc a EL EC a EN a La I a ci Cr a A
Tl Fl a : a a GC EN CO EN EG ER al cE EO a La I I al a a a ER I A i
Ra EO a a EN EI :
El ic Cc I Kc Ee a ; a a a a a El a Ea I A
EL CL OL ol La
Rl Ec a El a EC LL : § x
Table 2 (continued)
SD EL LA EE LI
A iL A La
CY cd
A A 0 cL a
Sc ec oc 0 cc Co
So cc ec
Sl a cE cl CN Cc a
FY 0 cl Lo oc Kc
ELA a LL a Le at CR a
A LL Co a
Sc 0 Yc A och cc
Se Yc cc cl Ly
Sc cc al ca a LA = a 0 Cm
So cc a ci ha
Ec Lc a cc
Sc Ce cc
En Lo eC
Sc cc Cc al can eee
EE Ec a Lc
Rec Cc LL a
Ra ec cc
CL LA a La
LE LC LC i a
Table 2 (continued) oo
A A
EC a eh a ca
Fa lc a on oc Lc cca ch a a a Rc a cL
Fl Cc cf
A lc lc a fa cc ec cl i i a cc ch a cc CO i cc ec a ee CO cl ec
Fe el cl ch cc cc lc a cc ac lc cl a i ca a ca lc cy
A cc cl
Ke ca a ca a ccc cc a
Ke cc cc lc i Gy lc cc
OS cdc i a a cdc cc cc a ca
Fc ec ce i a a
Ec cc Bc a cc a
KG el ec a cc a fc coc cl ch A a cc ec a i i ec lc ec el ch A ci ec ch i ac cl a Lc
Table 2 (continued) -
A a aC A a i
Rc EE La
LE Cn Lon a I
Kl cc a ca ec cc ca cl a CO a a cc ce et i ili al ec cc a a cn a cc a a ci cc lc a a cc cc ce i a cc ee a cc a Ye cK al a cc AO ec el ad
KE i Cc a ic
Se ca LG a ec
FC
Cc cB ca a cc a cl cl
RO cc a
Re Cc a GL a cc i a
I ec a ct
Cc cD cL
Re cc a Lc
Rc a cS cc 0 0c lc lc i
Ka Cc
Rac Fc Cc a
Kc cc a ec cc a i
Table 2 (continued) .
YON BEE [v | <0 [x R [v I~ BE E g
Cl i Cl H | R19 J Cl 11 | B COPh | Cl | OPh | H | COMe a :
Ee ec CB ctl A . al | Ct H | R30 cl TE H COMe i a ci BN LA A La i LO cl a LA LA i cl A LA : of} ic | H | SOMe j Cl | OMe H | COtBu Cl F | F | RG 5
CrCl JH SOE [Cl OMe [H [CoMe {a [F HL :
Cl | & |H | SO:n Pr E | OMe |H cork {C1 |F |F RS :
Cc Fc A A 4
Table 2 (continued) :
FET
SE Ec Le Ec Ea
BEE cc cc A
RE cL cc al A a
RE cc GL cy
RE Sc CO ec Ce a Lc
REEL Gc GL Ec a an La
Ce a el ac Ly
BE cc a a ce
REE ca Ce A cl
RN GE a OF a SE a
RE CO Ca Lh ca
RE fc a mG
SEN GD Cc oc Ca CN
Ri CG CO oc
BE a ec a a i
RG CF Ce a a cc
BC cl Ca A Co Ku
Bl ce Cc
BERENS LA ico
BEE LC cK a a a cl |F F | SOsPr [&) Fe JR Cl {F CQ | COMe
Rl Lc ce el
BE YE uC ce a Bical
BE cc Gc a icc
GR cL A cl a
SET Sc Lc a
BE a cl
BEE Cc A Ec a
Bil Cc Re
BNE Ec Cc al a
Tabk 2 (continued) )
A LS A LI
A el ccm cm cy acc AO
SF Lc J GA BL ea a a ec) Kc LA A ic 0 cd Kc A cl al
A A cc Com A cat
KA Lc cc i a i
A LA ec cl ic
EC Kc a A LH ca eC LA a cal 0 ec Kc ec eH cl
A cc ec cl al
Kc cc EC A A ica
Cl | OMe | OMe COtBu tBu F ] Cl | COtBu a [F(a [Ez CI” | OMe | OMe | CoMe cc A a ca
FT cL Ac EG A ca
Bi Ec cl a cl
FA LA a cc cl BL ca oF ja [we [ob TMe TH [Coma (dex |F [FCO
Cl |F [CT [CGAP whe [OI |B COB [dex | F Me | COBa [CTF |O |SoMe [ube |F EENES iT Ta | Cos
Tablk 2 (continued) }
IS A LN LA A EN
Ph I CFy |H | COtBu [© [HB [cose NO. TF TT] Me | COtBu
Si ct cc a all ic
SA cc cc i A
KE a A ca ca
GL
SEE A cl a cca
SE EE cal a il al
RE Ne a ca a
Ki i cc
A cc a ce A id
Ra a a ic al Le
Ke A cc a ll LA cl
Sc ec i a a cl
SL
Bc cc ei a A cl
Be A a a cl a a
Ra ce A ca a
Bi a ct cel a ical a
Di ec a a LA Lc a
Tabk 3
F S OR ct Br 4 FS OR {FS OR
Nig rs A N? yr f N Pp = x
NC Xn Xn = N | Xn
F Zz FN e NC Za cl Me
PON rs. 5 ve rs on
N Xn NZ 7 x NZ =
NC NC | Xn Xn
Cl ct F F NC
Me rs on CF, 7s CF, Fs oR
FC a > “ oe >
Me NC g NC a Xa
OMe _s om OMe _ o OMe oon 4 NF N 4 ZN 3
N xa {WN | Fx NY xn
E NC PL cl NC > OMe NC re SF St js OR ge Meo on
N? ZZ Ni oo 7 >
NC Xn NC Xa Ce
F F NC
CAN P
A pe SEE
X N
Ss OR S OR if me Me J Me 7S OR «La yn A? 2 velo J P
NC 7 NC xn I. xn
Oe Py Old T rs. 3
N IN ANF
Xn N Xn N ne Cpe OF Ce
Ss OR X, S X : { Z RS fj AN Z N, '& x iy o MeN JT Sx [WN o - Sal "
X; F X; a Noy
Ss OR X,
Ne XC x x
EC
J I EC cE KN LL
ESC NN CO Lo
EE Ce Lc LN i i ic LI
SS YF i ec
CE EY CO ec Cc co
SE CO EY Cc cm
SSCS KC cL cL co a LA - a Co i
RZ {2 16Fy Ri :
COtBu 2,46-F, R2 ; 2-Me-3.4-F, { Rl i 703, COtBu .
Me R2 2C34F, [RI =]
OI Ca = a EE a
Table 4 4
B ,
B
S B . a OR CF 7S R Me S OR Ci
A NF Z qj 3,
N ATW ASN ANF :
NC N
NC NC
B : 8 B ie
S B &
BAL pen oe
NC N . 8 :
B SS
YS OR F B # a FS Rd § OR Br z
A ANF PP / ;
NC NC N :
F NC 5
B 5
B 5 s OR B ; ba 7 ys A Ss OR CF
A Pp Pr PP 4 3 .
NC N
NC NC cl 8 B
Ss OR B
TS Pp Me o> OR Me be A Me B
NC Iw, : N i a NC, :
B 5 . :
S OR OMe =
TS P be OR OMe ys OR OMe E
ATTN A NSS aL
NC NC 22
F cl NGteo :
E hb % :
EN CL FN £2 LI CO CNT
SC a Lc Cc
SE i Cc 0 i cc CS a
RC a cc TN a
CC i CO a La La ec a cc A LO Kc
SE a el a cc LA LA LC 2-Br-3-F-Ph H COtBu | 2-OMe-4,5-F.Ph H Cod [F Ta [coda
SS CO ch Ml a Kal
EE La ci LB a La
EE a ON LI La
SE Lc ca
ECS cL ca EN Cl Lica
EN cc
BE I i EY i cy Ll cl
RS a FY I i] Kc a call a i i Li cal
SEN hc LL LN cl 2.CF¢3.6-F»-Ph E | COtBu iPr | H COtBu a eT LC i Yo cl EL call
Ec LB cc ccc co
EE a cl ES a cL
EE ON a SE a EL La a CE Lc BB ca
AEN el TL LI EL LI
Table 4 (continued)
TN I LN EE EN EI EN ET a i El al i i Gia a
Re a ic ec al cial al
GE ce a i cl a ical ca } 2-F-6-Me-Ph | B+ | COtBu tBu cHex | COtBu i 2-CH6-F-Ph [Et | COtBu § 2-Me.Ph F COtBu
SC a A ca a ia LA ca 2-Cl-6F-Ph [iPr | COtBu 2.F-6-CF-Ph | Ph i COtBu {2.CL6-F-Ph EB | COtBu 2-F6Me-Ph [Ph [COtBu | tBu cl | CotBu oo
Ee ce cl am a ih il cl el ial
ZF-6-MePh | CF, [coms F<Bu COMe | COB 2-CL6F-Ph | CF, | COBu_{ 2MeFh COEt | COtBu aa i (Insecticides and Acaricides) Co
Compositions containing the compounds of the present invention obtained in such ways as those mentioned above are useful, for example, as agricultural and horticultural insecticides, acaricides, sanitary insect pest controlling agents and anti- fouling agents for aqueous adhesive organisms. It is particularly preferable to apply compositions containing the compounds of the present invention as agricultural and horticultural insecticides and acaricides.
The compounds of the present invention can be used in the pure form without adding other ingredients, when they are actually applied as agricultural and horticultural insecticides or acaricides. When applied as agrochemicals, they may be used in forms that general agrochemicals can take, such as wettable powders, granules, dusts, emulsifiable concentrates, water soluble powders, flowable concentrates and flowables.
In order to make solid formulations, vegetable powders such as soybean flour and wheat flour; fine mineral powders such as diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophylite and clay; and organic and inorganic compounds such as sodium benzoate, urea and Glauber’s salt can be used as additives and carriers. When the purpose is to prepare liquid formulations, as additives and carriers, petroleum fractions such as kerosene, xylene and solvent naphtha, cyclohexane, cyclohexanone, DMF,
DMSO, alcohol, acetone, trichloroethylene, methyl isobutyl ketone, mineral oils, vegetable oils, water and the like can be used as solvents.
It is possible to further add surfactant, if required, to make these formulations homogeneous and stable forms. There are no particular restrictions on surfactant used.
Their examples include nonionic surfactant such as polyoxyethylene-added alkylphenyl ethers, polyoxyethylene-added alkyl ethers, polyoxyethylene-added higher fatty acid esters, polyoxyethylene-added sorbitan higher fatty acid esters and polyoxyethylene- added tristylylphenyl ethers; polyoxyethylene-added alkylphenyl ether sulfates, alkylbenzenesulfonates, higher alcohol sulfates, alkylnaphthalene sulfonates, polycarboxylic acid salts, lignin sulfonates, condensation products of alkylnaphthalene sulfonates with formaldehyde, and copolymers of isobutylene and maleic anhydride.
An amount of the active ingredient (a compound of the present invention) in a formulation is preferably 0.01 to 90% by weight, more preferably about 0.05 to 85% by weight. The obtained wettable powders, emulsifiable concentrates, flowable concentrates and flowables are diluted with water to specified concentrations to use as suspensions or emulsions. The dusts and granules are used as they are to directly spray on plants or soil.
It goes without saying that the compounds of the present invention are sufficiently effective by themselves. They can be used, however, by mixing with one or more of various fungicides, insecticides, acaricides or synergists.
Representative examples of fungicides, insecticides, acaricides and plant growth regulators that can be used to mix with the compounds of the present invention are shown in the following:
Fungicides:
Captan, Forpet, Thiuram, Ziram, Zineb, Maneb, Mancozeb, Propineb,
Polycarbamate, Chlorotalonyl, Quintozene, Captafol, Iprodione, Prothimidon,
Vinclosolin, Fluorimide, Cymoxanil, Mepronyl, Flutoranyl, Penthichlon, Oxycarboxin,
Phosethyl-aluminum, Propamocarb, Triazimefon, Triazimenol, Propiconazole,
Dichloptrazole, Bitertanol, Hexaconazole, Microbutanil, Flusilazole, Ethaconazole,
Fluotrimazole, Flutriafen, Penconazole, Diniconazole, Cyproconazole, Phenalimol,
Triflumizole, Prochloraz, Imazaryl, Pefurazoate, Tridemorph, Fenpropymorph, Triforin,
Buthiobate, Pryfenox, Anilazine, Polyoxin, Metharaxyl, Oxadixyl, Flaraxyl,
Isoprothiorane, Probenazole, Pyrolnitrin, Blasticidin S, Kasugamycin, Validamycin,
Sulfric acid dihydrostreptomycin, Benomil, Carbendazim, Thiophanate-methyl,
Hymexazole, Basic copper chloride, Basic copper sulfate, Triphenyl tin acetate,
Triphenyl tin hydroxide, Diethofencarb, Methasulfocarb, Quinomethionate, Binapacryl,
Lecithin, Sodium carbonate, Dithianon, Dinocap, Phenaminosulf, Dichlomezine,
Guazatine, Dozin, IBP, Edifenphos, Mepanipyrim, Ferimzone, Trichlamide,
Methasulfocarb, Fluazinam, Etokinorakku (oxolinic acid), Dimethomorph, Pyroquiron,
Tecrofutaram, Futharide, Phenazinoxyde, Thiabendazole, Tricyclazole, Vinclozolin,
Cymoxanil, Cyclobutanyl, Guazatine, Propamocarb-hydrochloride, Oxolinic acid and the like.
Insecticides and Acaricides:
Organophosphorus and Carbamate Insecticides:
Fenthion, Fenitrothion, Diazinon, Chlorpyrifos, ESP, Vamidothion, Fenthoate,
Dimethoate, Formothion, Malathon, Trichlorfon, Thiomethon, Phosmet, Dichlorvos,
Acephate, EPBP, Methylparathion, Oxydimethonmethyl, Ethion, Salithion, Cyanophos,
Isoxathion, Pyridafenthion, Phosalon, Methidathion, Sulprofos, Chlorfenvinphos,
Tetrachlorvinphos, Dimethylvinphos, Propaphos, isofenphos, Ethylthiomethon,
Profenofos, Pyrachlofos, Monoclotophos, Adinphosmethyl, Aldicarb, Methomyl,
Thiodicarb, Carbofuran, Carbosulfan, Benfuracarb, Furathiocarb, Propoxur, BPMC,
MTMC, MIPC, Carbaryl, Pyrimicarb, Ethiofencarb, Fenoxycarb and the like.
Pyrethroid Type Insecticides:
Permethrin, Cypermethrin, Deltamethrin, Fenvalerate, Fenpropathrin, Pyrethrin,
Allethrin, Tetramethrin, Resmethrin, Dimethrin, Propathrin, Phenothrin, Prothrin,
Fulvalinate, Cyfluthrin, Cyhalothrin, Flucythrinate, Ethofenprox, Cycloprothrin,
Tralomethrin, Silafluofen, Profenprox, Acrynathrin and the like.
Benzoyl urea and other insecticides:
Diflubenzuron, Chlorfluazuron, Hexaflumron, Triflumron, Tetrabenzuron,
Flufenoxuron, Flucycloxuron, Buprofezin, Pyriproxyfen, Methoprene, Benzoepin (endosulfan), Diafenthiuron, Acetamiprid, Imidacloprid, Nitenpyram, Fipronyl, Caltop,
Thiocyclam, Bensultap, Chlorphenapyr, Emanectin-benzoate, Tebufenozide, Nicotine sulfate, Rotenone, Metaldehyde, machine oils, BT, agrochemicals for microbial organisms such as insect disease viruses, and the like,
Nematicides:
Phenamiphos, Fosthiazate and the like.
Acaricides;
Chlorbenzylate, Phenisobromolate, Dicofol, Amitraz, BPPS, Benzomate,
Hexythiazox, Fenbutatin oxide, Polynactins, Quinomethionate, CPCBS, Tetradifon,
Abermectin, Milbemectin, Clofentezin, Cyhexatin, Pyridaben, Fenpyroximate,
Tebufenpyrad, Pyrimidifen, Phenothiocarb, Dienochlor, Etoxazole, Halfenprox and the like.
Plant growth regulators:
Gibberellins (for example, gibberellin A3, gibberellin A4 and gibberellin A7), IAA,
NAA and the like.
The compound of the present invention can be used to control agricultural pests, sanitary insect pests, stored grain insect pests, cloth insect pests, house insect pests and the like, and have activities of killing adults, nymphs, larvae and eggs. Their representative examples are shown in the following:
Examples of Lepidopterous pest insects include cotton leafworm, cabbage armyworm, black cutworm, common cabbegeworm, cabbage looper, diamond-back, smaller tea tortrix, tea leaf roller, peach fruit moth, oriental fruit moth, citrus leaf miner, tea leaf roller, apple leaf miner, gypsy moth, tea tussock moth, rice stem borer, grass leaf roller, European corn borer, fall webworm, almond moth, Heliothis sp.,
Helicoverpa sp., Agrotis sp., casemaking clothes moth, codling moth and cotton bollworm.
Examples of Hemipterous pest insects include green peach aphid, cotton aphid, turnip aphid, grain aphid, bean bug, common green stink bug, arrowhead scale, mulberry mealy scale, greenhouse whitefly, tabacco whitefly, pear psylla, Japanese pear lace bug, brown planthopper, small brown planthopper, white-backed planthopper and green rice leafhopper.
Examples of Coleopterous pest insects include striped flea beetle, cucurbit leaf beetle, Colorado potato beetle, rice water weevil, rice weevil, adzuki bean weevil,
Japanese beetle, soybean beetle, Diabrotica sp., cigarette beetle, powder post beetle, pine sawyer, white-spotted longicorn beetle, Agriotis sp., 28-spotted ladybeetle, rust-red flour beetle and cotton boll weevil.
Examples of Dipterous pest insects include housefly, Calliphora lata,
Boettcherisca peregrina, cucurbit fruit fly, citrus fruit fly, seed maggot, rice leaf miner, yellow drosophila, Stomoxys calcitrans, Culex tritaeniarhynchus, Aedes aegypti and
Anopheles hyrcanus.
Examples of Thysanopterous pest insects include Thrips palmi and tea thrips.
Examples of Hymenopterous pest insects include Monomorium pharaonis, yellow harnet and cabbage sawfly. :
Examples of Orthopterous pest insects include grasshopper.
Examples of Dictyopterous pest insects include German cockroach, American cockroach and Japanese cockroach. }
Examples of Isopterous pest insects include Formosan subterranean termite and
Reticulitermes speratus Kolbe.
Examples of Aphanipterous pest insects include human flea.
Examples of Anoplurous pest insects include human louse.
Examples of mites include two-spotted spider mite, Kanzawa spider mite, citrus red mite, European red mite, citrus rust mite, apple rust mite, Tarsonemus sp.,
Brevipalpus sp., Fotetranychus sp., Robin bulb mite, common grain mite,
Desmatophagoides farinae, Boophilus microplus and Haemaphysallis bispinosa.
Examples of plant-parasitic nematodes include southern root-knot nematode, root lesion nematode, soybean cyst nematode, rice white-tip nematode and pine wood nematode.
Many pests such as diamond-back, planthoppers, leafhoppers and aphids, and phytophagous mites have developed resistance against organophosphorus pesticides, carbamate insecticides and acaricides. Therefore, the chemicals have had the problem of lack of efficacy. There has been a desire for chemicals effective on pests and mites of resistant strains. The compounds of the present invention are chemicals having excellent insecticidal and acaricidal effects on pests resistant to organophosphorus pesticides, carbamate insecticides or pyrethroid type agents and mites resistant to acaricides, as well as those of sensitive strains.
The compounds of the present invention induce very slight chemical injuries, have low toxicity on fish and warm-blood animals, and are highly safe.
Best Forms to Implement the Invention:
The present invention is further described in detail in reference to a Reference
Example and Examples.
Reference Example 1
Preparation of 2-[4-(2,6-difluorophenyl)-2-thiazolyl]-3-hydroxy-2-trifluoromethy- cinnamonitrile
CF; H
YA + OM — EF s OU Ch [ NZ CH CN oh ~~ = F
F N
F CN
To a solution of 0.8g (4.2 mmol) of 2-trifluoromethylbenzoic acid in 10 ml of THF was added 0.69g (4.2 mmol) of carbonylbisimidazole, followed by stirring at room temperature for an hour. To the mixture was added 1.0g(4.2 mmol) of 2-cyanomethyl-4- (2,6-difluorophenyl)thiazole, and then, 0.17g (4.2 mmol) of sodium hydride (60% in oil) in an ice-bath. After stirring at room temperature for an hour, another equivalent of sodium hydride (0.17g, 4.2 mmol : 60% in oil) was added, followed by stirring at room temperature overnight. The reaction mixture was poured into ice-water, acidified with dilute hydrochloric acid, and then, extracted with ethyl acetate. The organic layer was concentrated under diminished pressure, followed by chromatography on silica-gel column (ethyl acetate/n-hexane = 1/1, as an eluent) to give 1.1g(64%) of the title compound. Melting point : 170-172C.
Example 1
Preparation of 2-[4-(2,6-difluorophenyl)-2-thiazolyl]-3-pivaloyloxy-2’- trifluormethyl-cinnamonitrile (Compound No. 3-1) ro tm
Foy : o cr
NL ~~ F S 3 { 7 ON \ —_— [
Ny N N
F CN
To a solution of 0.6g (1.5 mmol) of 2-[4-(2,6-difluorophenyl)-2-thiazolyl]-3- hydroxy-2'-trifluoromethylcinnamonitrile in 5 ml of THF were added 0.16g (1.6 mmol) of triethylamine and 0.2g (1.6 mmol) of pivaloyl chloride in an ice-bath, respectively, and then, the mixture was stirred at room temperature for 2 hours. After the precipitate was filtered, the filtrate was concentrated under diminished pressure, followed by chromatography on silica-gel column (ethyl acetate/n-hexane = 1/4, as an eluent) to give 0.28¢g (39%). Melting point : 163-165C.
Representative examples of the compounds of the present invention that were prepared in such ways as described above are shown in Table 5. The NMR data of oily substances and others are in Table 6.
The symbols used in the tables have the same meanings as those for Tables 1 to 4.
Table 5 bs OR
A ar a .
CN . a ET cl 1 Jo emrioen [i Jeorss Jeter, Jmeiienis f= [oorion fu Jone rer nseienis ss Jo ecroen w Jooms fren, Tunica ss [petri Jeorsy Jour Turan]
CE EA I CE ER CR ITT YTTI
CE ET CTO EO ES FT Tere FA
EN ENP TI CTT TR Sr ACT ZT
CON EC I CTT Er (IY TTTR TY sis focien n Jeowss fren, vicows oir sro [ov Jeorss [ror mri sies
Foi [ew cose Joetr Jvireows oii soy [ores Jn Tn ewe Tuseies ar] * [ ]: Melting point °C, and np: refractive index. These are the same for the following tables. a: One of isomers. Others are a mixture of isomers. b: Isomer of Compound No. 5-85.
Table 5 (continued) . 5-27 |2. 6-F,~Ph [H CO.nPr 2—Me Viscous oii
SC GA A CN VS LN a A a CN CL a CG cS LE LLL
SE LL il LSA
EC Ci RLS a ec LE SL 0 CO Gc ANAL
EN LoL
EE i MALL
EE CC CO Gi LAL
A EL I A CE A
EE GC 2 ON LLL LL
EE A A LS Ch 5-58 |3-F-FPh JH |COPh |2 Me {148~149]
Table 5 (continued)
A B 'R Xn Physical constant*
SE i GC UL
SE i GC CO LA SLE
EE CE LALA
Si I CL Lela
SE GC GO GCA CC LI
SE G0 Lh i VAR
EA EY CL CS SLL
SE Ge Ch CCR AA
EE GA CALE CC ELE
A CE CLE GN CLE RO LEE
WA ELE GI CLE CC EL
SA ch LO LEA
SSA OE CN CCRT CC LL
SN A cH ELSA 5-79 |[2-Cl-6-F=-Ph |H [coTER PCF. lEO=TEAT
I GA CELE CC LEU
SE a NL LEAL ch CC
SE eo GN LE AL
SIS Ee CE CR Le
Table 5 (continued) al EY I ET ol nn a On
Ph . 5-91 2—-OMe - 3, §—~F,LH COtBu [2-Me ”
I ON el CN ARC I eC dc Ca a
Ed a Gi ch [oT fete fren trea —
EE CE Gc A
Nc CLL SALA By
EC fc CASALL
SA CE GN CN CC LL
EC CA GI i CC LSS
SC CI i CC LLL
SERA EC CI i dl LAR LLL
EC I cl AS
SL lc ci
SE I dc CO dS
El Go
ER ch a LS
EE EC Li a A I CO LL a
SR ER GN i Ch oC a
Table 6 NMR Data : [+] 5-7 1. 68andl. 70 (total 6H, 2s), 2. 06and2. 30 (total 3H, 25), 6. 90—7. 05 (2H. m). 7. 10-7. 49 (m) and? 59 (s) (total 10H) i" 5-11 1. 27andl. 33 (total 9H, 2s), 6. 8§3~7. 08 (2H, m), 7. 20-7. 70 (m) and7. 76 (s) (total 5H) 5~15 1. 29andl. 32 (total 9H, 2s), 6. 95-7. 12 (1H. m),
RE HE A SL OY LOE
1. 2%and1l. 32 (total SH, 25), 7. 03-7. 40 (3H. m). a UE a a a 5-17 1. 28andl. 30 (total 9H. 2s). 7. 00-7. 19 (2H, m),
I ER Hr AA Lr POR CE LL 1. 29andl. 30 (total 9H, 28), 7. 25-7. 51 (4H, m),
RR ER A PA SA
5-19 1. 28andl. 31 (total 9H, 25), 7. 30-7. 41 (2H, m), 5-21 1. 10. 1. 32. 1. 33and1. 36 (total 18H, 4s). 6. 89- 5-27 l. 92andl. 96 (total 3H. 2s), 1. 61-1. 79 (2H, m). 2. 34and2. 53 (total 3H. 2s), 4. 17and4. 18 (total
BER FR en 2. 48and2. 49 (total 3H, 2s), 5. 19and5. 21 (total 572%] 2H, 2s). 6. 92-7. 70 (13H. m) 5-31 1. 96 (3H, t). 1. B1~1. 98 (2H, m), 2. 53 (3H, 5), 2. 99
TE er 7. 76 (1H. bs) 5-34 1. 23andl. 29 (total SH, 25), 6. 90and 7. 01 (total totat 2H. 2t). 7. 20-17. 40 (1H. m), 7. 51-7. 98 (4H. m). 8. 20-8. 28 (1H, m) 2. 19. 2. 28, 2.33, 2. 35, 2. 44and2. 50 (total 9H, ae ST i mr re aR Ge 5-47 1. 30andl. 34 (total 9H, 2s), 7. 15—~7. 46andr. 59-
I ES
5-60 1. 29andl. 32 (total 9H, 2s), 2. 32and2. 50 (total 5-69 i. 30andl. 33 (total 9H, 2s). 2.37and2. 42 (total { 3H. 2s). 7. 18-7. 38 (2H, ml. 7. 63-7. 90 (7H, m) 1. 32andl1. 33 (total 9H, 25s). 2. 31. 2.739, 2. 12and
A A SL I Ey LE LIL 5-92 l. 30and1l. 33 (9H, 2s), 7. 14-7. 30. 7. 66-7. 90and
EN bs). 7. 23-7. 48 (4H, m) 5-110 1. 20-1. 37 (5H, m), 1. 335 (SH. 5s), 1. 73-1. 91 (3H. m)., 2. 11-2. 20 (2H, m), 2. 59 (3H, s). 2. 82-2.95
A few examples of compositions of the present invention are described below. Additives and addition ratios are not limited to those in the examples, and can be changed in a wide range. The ‘parts” used in the formulation examples are parts by weight.
Example 2 Wettable Powder
A compound of the present invention 40 parts
Diatomaceous earth 53 parts
Higher alcohol sulfate 4 parts
Alkylnaphthalene sulfonate 3 parts
The above compounds were mixed uniformly and pulverized finely to give a wettable powder containing 40% of the active ingredient.
Example 3 Emulsifiable concentrate
A compound of the present invention 30 parts
Xylene 33 parts
Dimethylformamide 30 parts
Polyoxyethylene alkylallyl ether 7 parts
The above compounds were mixed and solved to give an emulsifiable concentrate containing 30% of the active ingredient.
Example4 Dust
A compound of the present invention 10 parts
Talc 89 parts
Polyoxyethylene alkylallyl ether 1 part
The above compounds were mixed uniformly and pulverized finely to give a dust containing 10% of the active ingredient.
Example 5 Granules
A compound of the present invention 5 parts
Clay 73 parts
Bentonite 20 parts
Sodium dioctylsulfosuccinate 1 part
Sodium phosphate 1 part
The above compounds were sufficiently pulverized and mixed. Water was added to it to knead well, followed by granulation and drying to give granules containing 5% of the active ingredient.
Example 6 Flowable concentrate
A compound of the present invention 10 parts
Sodium lignin sulfonate 4 parts
Sodium dodecylbenzenesulfonate 1 part
Xanthane gum 0.2 parts
Water 84.8 parts
The above compounds were mixed and wet pulverized until the granule size became smaller than 1 u, to give a flowable concentrate containing 10% of the active ingredient.
Availability in Industry:
Examples are shown below that formulations containing compounds of the present invention, which were prepared according to such ways as described above, were applied as agricultural and horticultural insecticides and acaricides.
Test Example 1 Effects on Pseudaletia separata Walker
According to the instructions of the wettable powder described in the above Example 2, a wettable powder was diluted with water to make the compound concentration 125 ppm. Corn leaves were immersed in the solution for 30 seconds, air-dried and placed in a Petri dish containing 5 third instar larvae of Pseudaletia separata Walker. The dish was covered with a glass lid and placed in a thermostatic chamber of temperature of 25°C and relative humidity of 65%. Mortality was assessed 6 days after treatment. Each test was replicated twice.
The results show that the following compounds had mortality of 100 %. 5-1, 5-2, 5-3, 5-4, 5-5, 5-6, 5-7, 5-8, 5-9, 5-10, 5-11, 5-12, 5-13, 5-15, 5-16, 5-17, 5-18, 5-20, 5-21, 5-22, 5-23, 5-24, 5-25, 5-26, 5-27, 5-28, 5-30, 5-31, 5-33, 5-34, 5-38, 5-39, 5-40, 5-41, 5-48, 5- 49, 5-50, 5-51, 5-54, 5-56, 5-57, 5-58, 5-59, 5-60, 5-61, 5-62, 5-63, 5-64, 5-65, 5-66, 5-67, 5-68, 5- 69, 5-74, 5-78, 5-80, 5-83, 5-84, 5-85, 5-86, 5-87, 5-88, 5-96, 5-97, 5-99, 5-100, 5-101, 5-102, 5-103, 5-104, 5-105, 5-106, 5-107, 5-108, 5-109 and 5-110.
Chlordimeform used as a control killed 40% of the larvae.
Test Example 2 Effects on Aphis gossypii Glover
Adults of Aphis gossypii Glover were inoculated on cucumber seedlings planted in a 10-cm (diameter) pot and 10 days old after the germination. On the following day the adult aphids were removed. According to the instructions of the emulsifiable concentrate described in the above
Example 3, an emulsifiable concentrate was diluted with water to make a compound concentration 8 ppm. The diluted formulation was sprayed over the cucumber seedlings infested with hatched nymphs. The seedlings were placed in a thermostatic chamber of temperature of 25°C and relative humidity of 65%. Mortality was assessed 6 days after treatment. Each test was replicated twice.
The results show that the following compounds had mortality of 100 %. 5-1, 5-3, 5-4, 5-5, 5-6, 5-7, 5-8, 5-10, 5-12, 5-13, 5-15, 5-16, 5-20, 5-24, 5-25, 5-26, 5-27, 5- 28, 5-30, 5-31, 5-33, 5-38, 5-39, 5-40, 5-41, 5-44, 5-45, 5-49, 5-51, 5-52, 5-54, 5-55, 5-56, 5-57, 5- 58, 5-60, 5-61, 5-62, 5-63, 5-64, 5-65, 5-68, 5-69, 5-71, 5-74, 5-76, 5-77, 5-78, 5-79, 5-80, 5-83, 5- 84, 5-85, 5-86, 5-87, 5-88, 5-89, 5-90, 5-91, 5-96, 5-99, 5-100, 5-101, 5-102, 5-103, 5-104, 5-105, 5- 106, 5-107, 5-108, 5-109 and 5-110.
The known compounds shown in the following and used as controls killed none of the nymphs.
Control Compound A
A compound disclosed in Japanese Patent Laid-open No. Sho 53-92769
AS
Control Compound B
A compound disclosed in Japanese Patent Laid-open No. Sho 55-154963
JH tBn N NO
Control Compound C
A compound disclosed in EP 189960 ay ane
Control Compound D :
A compound disclosed in Japanese Patent Laid-open No. Sho 55-154962 +
NH2nBuz
Control Compound E
A compound disclosed in Japanese Patent Laid-open No. Hei 10-298169 and WO 95/29591
Claims (2)
1. A compound represented by Formula (1) / =~ A # —Kn " (1) [wherein A is halogen, C, 4 alkyl, C,4 haloalkyl, C, alkoxy, optionally substituted C, 4 cycloalkyl, optionally substituted pyridyl, optionally substituted thienyl, substituted phenyl or optionally substituted phenoxy; B is hydrogen, halogen, C, 4 alkoxycarbonyl, optionally substituted phenyl, C, alkyl, C, haloalky! or C, 4 cycloalkyl; Ris Cig alkyl, a group of Formula COR! (wherein Ris C,, alkyl, C, ¢ haloalkyl, optionally substituted C; 4 cycloalkyl, C, 4 alkoxy, C, alkoxy C4 alkyl, C, alkylthio C, 4 alkyl, mono-C, alkylamino, di-C, 4 alkylamino, optionally substituted phenyl C, 4 alkyl, optionally substituted phenoxy C,; alkyl, optionally substituted phenylthio C, alkyl or optionally substituted phenyl), or a group of Formula SO,R? (wherein R? is C, 4 alkyl or optionally substituted phenyl); X is cyano, nitro, halogen, C, 4 alkyl, C, 4 haloalkyl, C,¢ alkoxy, C, haloalkoxy, optionally substituted phenyl! or optionally substituted phenoxy; and n is an integer between 1 and 5].
2. A pest controlling agent containing one or more compounds of Formula (1) / =~ A YZ —Xn " (1) {wherein A, B, R, X and n are as defined above) as active ingredients.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP26332398 | 1998-09-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200101399B true ZA200101399B (en) | 2001-11-29 |
Family
ID=27677716
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200101399A ZA200101399B (en) | 1998-09-17 | 2001-02-20 | Thiazolylcinnamonitriles and pest controlling agents. |
Country Status (1)
Country | Link |
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ZA (1) | ZA200101399B (en) |
-
2001
- 2001-02-20 ZA ZA200101399A patent/ZA200101399B/en unknown
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