PL113231B1 - Insecticide - Google Patents
Insecticide Download PDFInfo
- Publication number
- PL113231B1 PL113231B1 PL1977220785A PL22078577A PL113231B1 PL 113231 B1 PL113231 B1 PL 113231B1 PL 1977220785 A PL1977220785 A PL 1977220785A PL 22078577 A PL22078577 A PL 22078577A PL 113231 B1 PL113231 B1 PL 113231B1
- Authority
- PL
- Poland
- Prior art keywords
- hydrogen
- chlorine
- bromine
- methoxy
- group
- Prior art date
Links
- 239000002917 insecticide Substances 0.000 title claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 87
- 239000001257 hydrogen Substances 0.000 claims description 86
- 229910052801 chlorine Inorganic materials 0.000 claims description 82
- 239000000460 chlorine Substances 0.000 claims description 81
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 70
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 65
- 229910052794 bromium Inorganic materials 0.000 claims description 62
- 150000001875 compounds Chemical class 0.000 claims description 61
- 229910052731 fluorine Chemical group 0.000 claims description 55
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 52
- 239000011737 fluorine Chemical group 0.000 claims description 52
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 51
- 150000002431 hydrogen Chemical class 0.000 claims description 49
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
- -1 hydroxy, phenyl Chemical group 0.000 claims description 33
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 29
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 20
- 239000004480 active ingredient Substances 0.000 claims description 19
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical group CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 16
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 16
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 16
- 125000002541 furyl group Chemical group 0.000 claims description 16
- 125000001544 thienyl group Chemical group 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 125000004076 pyridyl group Chemical group 0.000 claims description 13
- 125000001624 naphthyl group Chemical group 0.000 claims description 12
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 11
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 11
- 125000005493 quinolyl group Chemical group 0.000 claims description 11
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 10
- 125000000335 thiazolyl group Chemical group 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 9
- 229910052717 sulfur Chemical group 0.000 claims description 7
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims description 2
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical group NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 32
- 241000238631 Hexapoda Species 0.000 description 29
- 238000012360 testing method Methods 0.000 description 29
- 239000013543 active substance Substances 0.000 description 13
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- 241000196324 Embryophyta Species 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 241000894007 species Species 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 239000000843 powder Substances 0.000 description 7
- 230000000749 insecticidal effect Effects 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 235000011299 Brassica oleracea var botrytis Nutrition 0.000 description 5
- 235000017647 Brassica oleracea var italica Nutrition 0.000 description 5
- 240000003259 Brassica oleracea var. botrytis Species 0.000 description 5
- 241001301805 Epilachna Species 0.000 description 5
- 235000013601 eggs Nutrition 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 230000009466 transformation Effects 0.000 description 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
- 241000462639 Epilachna varivestis Species 0.000 description 4
- 241000382353 Pupa Species 0.000 description 4
- 241001521235 Spodoptera eridania Species 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 150000002367 halogens Chemical group 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- MNOULQLXILYKNV-UHFFFAOYSA-N 5-[4-(trifluoromethyl)phenyl]-1h-pyrazole Chemical group C1=CC(C(F)(F)F)=CC=C1C1=CC=NN1 MNOULQLXILYKNV-UHFFFAOYSA-N 0.000 description 3
- 241000255925 Diptera Species 0.000 description 3
- 241000907661 Pieris rapae Species 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 239000007900 aqueous suspension Substances 0.000 description 3
- 235000021186 dishes Nutrition 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- QUKGLNCXGVWCJX-UHFFFAOYSA-N 1,3,4-thiadiazol-2-amine Chemical compound NC1=NN=CS1 QUKGLNCXGVWCJX-UHFFFAOYSA-N 0.000 description 2
- NXDXMSTXCYCUGG-UHFFFAOYSA-N 2,6-dimethylbenzamide Chemical compound CC1=CC=CC(C)=C1C(N)=O NXDXMSTXCYCUGG-UHFFFAOYSA-N 0.000 description 2
- MALIONKMKPITBV-UHFFFAOYSA-N 2-(3-chloro-4-hydroxyphenyl)-n-[2-(4-sulfamoylphenyl)ethyl]acetamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CCNC(=O)CC1=CC=C(O)C(Cl)=C1 MALIONKMKPITBV-UHFFFAOYSA-N 0.000 description 2
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 2
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 241000254173 Coleoptera Species 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 241000238814 Orthoptera Species 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- QPFYXYFORQJZEC-FOCLMDBBSA-N Phenazopyridine Chemical group NC1=NC(N)=CC=C1\N=N\C1=CC=CC=C1 QPFYXYFORQJZEC-FOCLMDBBSA-N 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000000974 larvacidal effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910052901 montmorillonite Inorganic materials 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- 229940070891 pyridium Drugs 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- RHKPJTFLRQNNGJ-UHFFFAOYSA-N 1,3-benzothiazole-2-carbaldehyde Chemical group C1=CC=C2SC(C=O)=NC2=C1 RHKPJTFLRQNNGJ-UHFFFAOYSA-N 0.000 description 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- 125000006305 3-iodophenyl group Chemical group [H]C1=C([H])C(I)=C([H])C(*)=C1[H] 0.000 description 1
- WGRPQCFFBRDZFV-UHFFFAOYSA-N 3-methylbenzamide Chemical compound CC1=CC=CC(C(N)=O)=C1 WGRPQCFFBRDZFV-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- 241001136265 Agriotes Species 0.000 description 1
- 241000254177 Anthonomus Species 0.000 description 1
- 241000396431 Anthrenus scrophulariae Species 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- 241000238657 Blattella germanica Species 0.000 description 1
- 241001674044 Blattodea Species 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 241001340508 Crambus Species 0.000 description 1
- 244000000626 Daucus carota Species 0.000 description 1
- 235000002767 Daucus carota Nutrition 0.000 description 1
- 241000195955 Equisetum hyemale Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 241000257232 Haematobia irritans Species 0.000 description 1
- 241000255967 Helicoverpa zea Species 0.000 description 1
- 241001351188 Hylemya Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 241001177141 Lyctinae Species 0.000 description 1
- 241000255682 Malacosoma americanum Species 0.000 description 1
- 241000699729 Muridae Species 0.000 description 1
- 241000257229 Musca <genus> Species 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- QADBBZGQNGPIBT-UHFFFAOYSA-N N-methoxynitramide Chemical compound CON[N+](=O)[O-] QADBBZGQNGPIBT-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241001147398 Ostrinia nubilalis Species 0.000 description 1
- 241000237503 Pectinidae Species 0.000 description 1
- 241000238675 Periplaneta americana Species 0.000 description 1
- 241000257186 Phormia regina Species 0.000 description 1
- 241000595626 Plodia Species 0.000 description 1
- 235000005805 Prunus cerasus Nutrition 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000254152 Sitophilus oryzae Species 0.000 description 1
- 241000256251 Spodoptera frugiperda Species 0.000 description 1
- 241001494139 Stomoxys Species 0.000 description 1
- 241000333694 Thyridopteryx Species 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 229940054066 benzamide antipsychotics Drugs 0.000 description 1
- 150000003936 benzamides Chemical class 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- CRPOUZQWHJYTMS-UHFFFAOYSA-N dialuminum;magnesium;disilicate Chemical compound [Mg+2].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] CRPOUZQWHJYTMS-UHFFFAOYSA-N 0.000 description 1
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- ZXQYGBMAQZUVMI-GCMPRSNUSA-N gamma-cyhalothrin Chemical compound CC1(C)[C@@H](\C=C(/Cl)C(F)(F)F)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-GCMPRSNUSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 235000020637 scallop Nutrition 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 235000019195 vitamin supplement Nutrition 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65655276A | 1976-02-09 | 1976-02-09 | |
| US74016676A | 1976-11-10 | 1976-11-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL113231B1 true PL113231B1 (en) | 1980-11-29 |
Family
ID=27097215
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1977220785A PL113231B1 (en) | 1976-02-09 | 1977-02-09 | Insecticide |
| PL1977195892A PL112645B1 (en) | 1976-02-09 | 1977-02-09 | Process for preparing novel n-(1,3,4-thiadiazolylo-2)-benzamides |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1977195892A PL112645B1 (en) | 1976-02-09 | 1977-02-09 | Process for preparing novel n-(1,3,4-thiadiazolylo-2)-benzamides |
Country Status (30)
| Country | Link |
|---|---|
| JP (1) | JPS52105173A (OSRAM) |
| AR (1) | AR221204A1 (OSRAM) |
| AT (1) | AT362192B (OSRAM) |
| AU (1) | AU505649B2 (OSRAM) |
| BG (3) | BG28236A3 (OSRAM) |
| BR (1) | BR7700471A (OSRAM) |
| CA (1) | CA1077041A (OSRAM) |
| CH (1) | CH631603A5 (OSRAM) |
| CS (1) | CS198217B2 (OSRAM) |
| DD (2) | DD135032A5 (OSRAM) |
| DE (1) | DE2704288A1 (OSRAM) |
| DK (1) | DK50677A (OSRAM) |
| ES (2) | ES455409A1 (OSRAM) |
| FR (1) | FR2340312A1 (OSRAM) |
| GB (1) | GB1571422A (OSRAM) |
| GR (1) | GR65893B (OSRAM) |
| HK (1) | HK27081A (OSRAM) |
| HU (1) | HU179458B (OSRAM) |
| IE (1) | IE44573B1 (OSRAM) |
| IL (1) | IL51149A (OSRAM) |
| IT (1) | IT1078058B (OSRAM) |
| KE (1) | KE3131A (OSRAM) |
| MY (1) | MY8200038A (OSRAM) |
| NL (1) | NL7701059A (OSRAM) |
| NZ (1) | NZ182937A (OSRAM) |
| PL (2) | PL113231B1 (OSRAM) |
| PT (1) | PT66158A (OSRAM) |
| RO (2) | RO76588A (OSRAM) |
| SE (1) | SE412063B (OSRAM) |
| SU (1) | SU706023A3 (OSRAM) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1983980A4 (en) * | 2006-01-25 | 2010-05-05 | Synta Pharmaceuticals Corp | THIAZOL AND THIADIAZOL COMPOUNDS FOR USES IN RELATION TO INFLAMMATION AND IMMUNITY |
| EP2107054A1 (en) * | 2008-04-01 | 2009-10-07 | Università Degli Studi Di Milano - Bicocca | Antiproliferative compounds and therapeutic uses thereof |
| MX2012011784A (es) | 2010-04-16 | 2013-03-21 | Bayer Ip Gmbh | Nuevos compuestos heterociclicos como pesticidas. |
| CN103188936B (zh) * | 2010-08-31 | 2016-04-20 | 陶氏益农公司 | 杀虫组合物 |
| WO2012121168A1 (ja) * | 2011-03-04 | 2012-09-13 | 国立大学法人京都大学 | キナーゼ阻害剤 |
| WO2014060381A1 (de) | 2012-10-18 | 2014-04-24 | Bayer Cropscience Ag | Heterocyclische verbindungen als schädlingsbekämpfungsmittel |
| WO2015132313A1 (de) * | 2014-03-06 | 2015-09-11 | Bayer Cropscience Ag | Heterocyclische verbindungen als schädlingsbekämpfungsmittel |
| CN110382493A (zh) * | 2016-12-16 | 2019-10-25 | 拜耳农作物科学股份公司 | 作为农药的噻二唑衍生物 |
| JP2020502217A (ja) * | 2016-12-22 | 2020-01-23 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 置換ヘテロアリールピロロンおよびその塩ならびに除草活性物質としてのその使用 |
| CN109456283B (zh) * | 2018-12-13 | 2023-03-28 | 贵州大学 | 含1,3,4-噻二唑硫醚(砜)的2-(三氟甲基)苯甲酰胺类衍生物、其制备及应用 |
-
1976
- 1976-12-18 GR GR52438A patent/GR65893B/el unknown
- 1976-12-20 IE IE2783/76A patent/IE44573B1/en unknown
- 1976-12-21 NZ NZ182937A patent/NZ182937A/xx unknown
- 1976-12-22 CA CA268,463A patent/CA1077041A/en not_active Expired
- 1976-12-23 IL IL51149A patent/IL51149A/xx unknown
-
1977
- 1977-01-11 AR AR266147A patent/AR221204A1/es active
- 1977-01-25 SE SE7700778A patent/SE412063B/xx unknown
- 1977-01-26 BR BR7700471A patent/BR7700471A/pt unknown
- 1977-01-27 ES ES455409A patent/ES455409A1/es not_active Expired
- 1977-02-01 SU SU772446348A patent/SU706023A3/ru active
- 1977-02-02 NL NL7701059A patent/NL7701059A/xx not_active Application Discontinuation
- 1977-02-02 DE DE19772704288 patent/DE2704288A1/de not_active Ceased
- 1977-02-03 BG BG035326A patent/BG28236A3/xx unknown
- 1977-02-03 BG BG037894A patent/BG28987A4/xx unknown
- 1977-02-03 BG BG037893A patent/BG28986A4/xx unknown
- 1977-02-03 GB GB4389/77A patent/GB1571422A/en not_active Expired
- 1977-02-04 PT PT66158A patent/PT66158A/pt unknown
- 1977-02-07 AU AU22026/77A patent/AU505649B2/en not_active Expired
- 1977-02-07 CH CH146977A patent/CH631603A5/de not_active IP Right Cessation
- 1977-02-07 HU HU77EI725A patent/HU179458B/hu unknown
- 1977-02-07 DK DK50677A patent/DK50677A/da not_active Application Discontinuation
- 1977-02-08 IT IT20057/77A patent/IT1078058B/it active
- 1977-02-08 CS CS77822A patent/CS198217B2/cs unknown
- 1977-02-08 AT AT81877A patent/AT362192B/de not_active IP Right Cessation
- 1977-02-09 PL PL1977220785A patent/PL113231B1/pl unknown
- 1977-02-09 JP JP1404977A patent/JPS52105173A/ja active Pending
- 1977-02-09 PL PL1977195892A patent/PL112645B1/pl unknown
- 1977-02-09 DD DD77204378A patent/DD135032A5/xx unknown
- 1977-02-09 DD DD7700197305A patent/DD130038A5/xx unknown
- 1977-02-09 FR FR7703603A patent/FR2340312A1/fr active Granted
- 1977-02-13 RO RO7796600A patent/RO76588A/ro unknown
-
1978
- 1978-02-16 ES ES467061A patent/ES467061A1/es not_active Expired
-
1979
- 1979-02-17 RO RO7996599A patent/RO76587A/ro unknown
-
1981
- 1981-06-02 KE KE3131A patent/KE3131A/xx unknown
- 1981-06-18 HK HK270/81A patent/HK27081A/xx unknown
-
1982
- 1982-12-30 MY MY38/82A patent/MY8200038A/xx unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI537264B (zh) | 殺蟲組成物及與其相關之方法 | |
| JPS63233903A (ja) | Ｎ−シアノイソチオ尿素の昆虫及び植物損傷性線虫防除のための使用法 | |
| PL113231B1 (en) | Insecticide | |
| US4141984A (en) | N-(1,3,4-thiadiazol-2-yl)benzamides | |
| PL102954B1 (pl) | Srodek owadobojczy | |
| US5391561A (en) | Halopropargyl compounds, compositions, uses and processes of preparation | |
| US5292762A (en) | Halopropargyl compounds, compositions, uses and processes of preparation | |
| JPS63267752A (ja) | 殺虫性のｎ−（場合により置換された）−ｎ′−置換−ｎ，ｎ′−ジ置換ヒドラジン | |
| US4271166A (en) | N-(1,3,4-Thiadiazol-2-yl)benzamides | |
| EP0285565A2 (de) | 2-Mercapto-5-pyridyl-1,3,4-oxadiazole und -1,3,4-thiadiazole, Verfahren zu ihrer Herstellung und ihre Verwendung als nematizide Mittel | |
| JPS6326757B2 (OSRAM) | ||
| JPH02138279A (ja) | 有害生物の防除のための ２，５‐ビス（ピリジル）‐１，３，４‐チアジアゾールの用途 | |
| JPS63126804A (ja) | 農園芸用殺虫組成物 | |
| CS207649B2 (en) | Insecticide means and method of making the active substances | |
| KR810000057B1 (ko) | N-(1,3,4-티아디아졸-2-일) 벤즈아마이드 유도체의 제조방법 | |
| US4812464A (en) | Pesticidal 2-pyridyl-4,5-dihydro-1,3,4-thiadiazoles | |
| JPH0368566A (ja) | ５‐置換３‐アリールインオキサゾール‐誘導体、その製法及びこれを含有する有害生物防除剤 | |
| EP0263066A2 (de) | 2-Mercapto-oxadiazol- und -thiadiazol-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende nematizide Mittel | |
| KR102035091B1 (ko) | 오가노설퍼기를 포함하는 피라졸 카복사마이드 화합물 및 이를 함유하는 살충제 조성물 | |
| JP3489624B2 (ja) | 有害生物を殺す作用のあるテトラゾール誘導体 | |
| HU189221B (en) | Herbicide compositions and process for producing heterocyclic compounds utilizable as active agents too | |
| KR810000603B1 (ko) | N-(1, 3, 4-티아디아졸-2-일)벤즈아미드의 제조방법 | |
| CN108752330A (zh) | 一种含1,2,4-噁二唑环的吡啶连吡唑-4-甲酰胺类化合物及其制备方法与应用 | |
| CS198218B2 (cs) | Zp&sob přípravy thiadiazolylbenzamidů | |
| CS207650B2 (cs) | Způsob výroby nových N-(l,3,4-thiadiazol-2-yl)benzamidů |