TR201816134T4 - Zararli kontrol ajani - Google Patents
Zararli kontrol ajani Download PDFInfo
- Publication number
- TR201816134T4 TR201816134T4 TR2018/16134T TR201816134T TR201816134T4 TR 201816134 T4 TR201816134 T4 TR 201816134T4 TR 2018/16134 T TR2018/16134 T TR 2018/16134T TR 201816134 T TR201816134 T TR 201816134T TR 201816134 T4 TR201816134 T4 TR 201816134T4
- Authority
- TR
- Turkey
- Prior art keywords
- compound
- compounds
- group
- reaction
- pest
- Prior art date
Links
- 241000607479 Yersinia pestis Species 0.000 title claims abstract description 76
- 150000001412 amines Chemical class 0.000 claims abstract description 21
- 239000003795 chemical substances by application Substances 0.000 claims description 58
- 238000000034 method Methods 0.000 claims description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
- 241000238631 Hexapoda Species 0.000 claims description 28
- 241000196324 Embryophyta Species 0.000 claims description 25
- 239000002689 soil Substances 0.000 claims description 20
- 235000007164 Oryza sativa Nutrition 0.000 claims description 18
- 235000009566 rice Nutrition 0.000 claims description 18
- 239000007787 solid Substances 0.000 claims description 14
- 241001465754 Metazoa Species 0.000 claims description 12
- 241001124076 Aphididae Species 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 206010007134 Candida infections Diseases 0.000 claims description 8
- 208000007027 Oral Candidiasis Diseases 0.000 claims description 8
- 241000287411 Turdidae Species 0.000 claims description 8
- 201000003984 candidiasis Diseases 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- 235000015097 nutrients Nutrition 0.000 claims description 6
- 241000437063 Phyllotreta striolata Species 0.000 claims description 5
- 235000006089 Phaseolus angularis Nutrition 0.000 claims description 4
- 240000007098 Vigna angularis Species 0.000 claims description 4
- 235000010711 Vigna angularis Nutrition 0.000 claims description 4
- 239000001963 growth medium Substances 0.000 claims description 3
- 238000009434 installation Methods 0.000 claims description 3
- DHQKLWKZSFCKTA-UHFFFAOYSA-N n-[1-[(6-chloropyridin-3-yl)methyl]pyridin-2-ylidene]-2,2,2-trifluoroacetamide Chemical compound FC(F)(F)C(=O)N=C1C=CC=CN1CC1=CC=C(Cl)N=C1 DHQKLWKZSFCKTA-UHFFFAOYSA-N 0.000 claims description 3
- 230000000149 penetrating effect Effects 0.000 claims description 2
- 241000209094 Oryza Species 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 description 94
- 239000000203 mixture Substances 0.000 description 60
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
- -1 2,6-dichloro-4-pyridyl group Chemical group 0.000 description 54
- 238000006243 chemical reaction Methods 0.000 description 53
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 53
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 51
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
- 125000005843 halogen group Chemical group 0.000 description 29
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 239000013078 crystal Substances 0.000 description 24
- 238000009472 formulation Methods 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- 239000002904 solvent Substances 0.000 description 22
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 239000002585 base Substances 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 230000000694 effects Effects 0.000 description 18
- 239000000126 substance Substances 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 15
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- 240000007594 Oryza sativa Species 0.000 description 14
- 125000000217 alkyl group Chemical group 0.000 description 14
- 239000000843 powder Substances 0.000 description 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 14
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 12
- 150000002170 ethers Chemical class 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
- 239000000575 pesticide Substances 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- 239000000969 carrier Substances 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 239000008187 granular material Substances 0.000 description 9
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- 150000001408 amides Chemical class 0.000 description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 7
- 238000007654 immersion Methods 0.000 description 7
- 230000000749 insecticidal effect Effects 0.000 description 7
- 239000002917 insecticide Substances 0.000 description 7
- 150000002576 ketones Chemical class 0.000 description 7
- 239000012669 liquid formulation Substances 0.000 description 7
- 238000000622 liquid--liquid extraction Methods 0.000 description 7
- 150000002825 nitriles Chemical class 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 238000000638 solvent extraction Methods 0.000 description 7
- 239000008096 xylene Substances 0.000 description 7
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 6
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 229940117389 dichlorobenzene Drugs 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 6
- 230000035515 penetration Effects 0.000 description 6
- 238000000634 powder X-ray diffraction Methods 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 150000003462 sulfoxides Chemical class 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 230000005945 translocation Effects 0.000 description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 241001674048 Phthiraptera Species 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 241001414989 Thysanoptera Species 0.000 description 5
- 239000002671 adjuvant Substances 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 238000000113 differential scanning calorimetry Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 238000005507 spraying Methods 0.000 description 5
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 4
- NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 description 4
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 4
- 150000008046 alkali metal hydrides Chemical class 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 235000006708 antioxidants Nutrition 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000004927 clay Substances 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 4
- 230000002262 irrigation Effects 0.000 description 4
- 238000003973 irrigation Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000008188 pellet Substances 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- KUGLJYVDCCITGB-UHFFFAOYSA-N 2,2,2-trifluoro-n-pyridin-2-ylacetamide Chemical compound FC(F)(F)C(=O)NC1=CC=CC=N1 KUGLJYVDCCITGB-UHFFFAOYSA-N 0.000 description 3
- 244000291564 Allium cepa Species 0.000 description 3
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- 241001414720 Cicadellidae Species 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 238000007707 calorimetry Methods 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 239000000428 dust Substances 0.000 description 3
- 238000004945 emulsification Methods 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 238000009501 film coating Methods 0.000 description 3
- 239000007888 film coating Substances 0.000 description 3
- 235000013312 flour Nutrition 0.000 description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000002574 poison Substances 0.000 description 3
- 231100000614 poison Toxicity 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 235000000346 sugar Nutrition 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
- ZOCSXAVNDGMNBV-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile Chemical compound NC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZOCSXAVNDGMNBV-UHFFFAOYSA-N 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 240000007124 Brassica oleracea Species 0.000 description 2
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 2
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 2
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 239000005899 Fipronil Substances 0.000 description 2
- 108010010803 Gelatin Chemical class 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- 241000257303 Hymenoptera Species 0.000 description 2
- 239000005906 Imidacloprid Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 230000000895 acaricidal effect Effects 0.000 description 2
- 239000000642 acaricide Substances 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
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 244000000054 animal parasite Species 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- 235000021329 brown rice Nutrition 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000005018 casein Substances 0.000 description 2
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical class NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 2
- 235000021240 caseins Nutrition 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000002050 diffraction method Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 239000003623 enhancer Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 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
- 239000000945 filler Substances 0.000 description 2
- 229940013764 fipronil Drugs 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 238000003958 fumigation Methods 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 239000008273 gelatin Chemical class 0.000 description 2
- 229920000159 gelatin Chemical class 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 238000005469 granulation Methods 0.000 description 2
- 230000003179 granulation Effects 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 229940056881 imidacloprid Drugs 0.000 description 2
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 150000004045 organic chlorine compounds Chemical class 0.000 description 2
- 244000045947 parasite Species 0.000 description 2
- 230000002688 persistence Effects 0.000 description 2
- 230000000361 pesticidal effect Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 230000008635 plant growth Effects 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000002453 shampoo Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- 239000000375 suspending 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
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 239000010455 vermiculite Substances 0.000 description 2
- 229910052902 vermiculite Inorganic materials 0.000 description 2
- 235000019354 vermiculite Nutrition 0.000 description 2
- 239000004562 water dispersible granule Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- 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 1
- RYAUSSKQMZRMAI-ALOPSCKCSA-N (2S,6R)-4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1C[C@H](C)O[C@H](C)C1 RYAUSSKQMZRMAI-ALOPSCKCSA-N 0.000 description 1
- ITOFPJRDSCGOSA-KZLRUDJFSA-N (2s)-2-[[(4r)-4-[(3r,5r,8r,9s,10s,13r,14s,17r)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H](CC[C@]13C)[C@@H]2[C@@H]3CC[C@@H]1[C@H](C)CCC(=O)N[C@H](C(O)=O)CC1=CNC2=CC=CC=C12 ITOFPJRDSCGOSA-KZLRUDJFSA-N 0.000 description 1
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
- XUNYDVLIZWUPAW-UHFFFAOYSA-N (4-chlorophenyl) n-(4-methylphenyl)sulfonylcarbamate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)OC1=CC=C(Cl)C=C1 XUNYDVLIZWUPAW-UHFFFAOYSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- 125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 description 1
- WCXDHFDTOYPNIE-RIYZIHGNSA-N (E)-acetamiprid Chemical compound N#C/N=C(\C)N(C)CC1=CC=C(Cl)N=C1 WCXDHFDTOYPNIE-RIYZIHGNSA-N 0.000 description 1
- CFRPSFYHXJZSBI-DHZHZOJOSA-N (E)-nitenpyram Chemical compound [O-][N+](=O)/C=C(\NC)N(CC)CC1=CC=C(Cl)N=C1 CFRPSFYHXJZSBI-DHZHZOJOSA-N 0.000 description 1
- QNBTYORWCCMPQP-JXAWBTAJSA-N (Z)-dimethomorph Chemical compound C1=C(OC)C(OC)=CC=C1C(\C=1C=CC(Cl)=CC=1)=C/C(=O)N1CCOCC1 QNBTYORWCCMPQP-JXAWBTAJSA-N 0.000 description 1
- CKPCAYZTYMHQEX-NBVRZTHBSA-N (e)-1-(2,4-dichlorophenyl)-n-methoxy-2-pyridin-3-ylethanimine Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=N/OC)/CC1=CC=CN=C1 CKPCAYZTYMHQEX-NBVRZTHBSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 description 1
- DSSGEOZAQMMSSU-UHFFFAOYSA-N 1-[(6-chloropyridin-3-yl)methyl]pyridin-2-imine Chemical compound C1=NC(Cl)=CC=C1CN1C(=N)C=CC=C1 DSSGEOZAQMMSSU-UHFFFAOYSA-N 0.000 description 1
- ISVPLFUDYVCXHM-UHFFFAOYSA-N 1-[(6-chloropyridin-3-yl)methyl]pyridin-2-imine;hydrochloride Chemical compound Cl.C1=NC(Cl)=CC=C1CN1C(=N)C=CC=C1 ISVPLFUDYVCXHM-UHFFFAOYSA-N 0.000 description 1
- WKBPZYKAUNRMKP-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)pentyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)CN1C=NC=N1 WKBPZYKAUNRMKP-UHFFFAOYSA-N 0.000 description 1
- MGNFYQILYYYUBS-UHFFFAOYSA-N 1-[3-(4-tert-butylphenyl)-2-methylpropyl]piperidine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1CCCCC1 MGNFYQILYYYUBS-UHFFFAOYSA-N 0.000 description 1
- PFFIDZXUXFLSSR-UHFFFAOYSA-N 1-methyl-N-[2-(4-methylpentan-2-yl)-3-thienyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound S1C=CC(NC(=O)C=2C(=NN(C)C=2)C(F)(F)F)=C1C(C)CC(C)C PFFIDZXUXFLSSR-UHFFFAOYSA-N 0.000 description 1
- NFGXHKASABOEEW-UHFFFAOYSA-N 1-methylethyl 11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate Chemical compound COC(C)(C)CCCC(C)CC=CC(C)=CC(=O)OC(C)C NFGXHKASABOEEW-UHFFFAOYSA-N 0.000 description 1
- STMIIPIFODONDC-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(O)(CCCC)CN1C=NC=N1 STMIIPIFODONDC-UHFFFAOYSA-N 0.000 description 1
- YABFPHSQTSFWQB-UHFFFAOYSA-N 2-(4-fluorophenyl)-1-(1,2,4-triazol-1-yl)-3-(trimethylsilyl)propan-2-ol Chemical compound C=1C=C(F)C=CC=1C(O)(C[Si](C)(C)C)CN1C=NC=N1 YABFPHSQTSFWQB-UHFFFAOYSA-N 0.000 description 1
- WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical compound NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 description 1
- JLZMZFJVTNYDOT-UHFFFAOYSA-N 2-aminoethenethiol Chemical compound NC=CS JLZMZFJVTNYDOT-UHFFFAOYSA-N 0.000 description 1
- SKCNYHLTRZIINA-UHFFFAOYSA-N 2-chloro-5-(chloromethyl)pyridine Chemical compound ClCC1=CC=C(Cl)N=C1 SKCNYHLTRZIINA-UHFFFAOYSA-N 0.000 description 1
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- XJFIKRXIJXAJGH-UHFFFAOYSA-N 5-chloro-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical group ClC1=CC=C2NC(=O)NC2=N1 XJFIKRXIJXAJGH-UHFFFAOYSA-N 0.000 description 1
- OEDUIFSDODUDRK-UHFFFAOYSA-N 5-phenyl-1h-pyrazole Chemical compound N1N=CC=C1C1=CC=CC=C1 OEDUIFSDODUDRK-UHFFFAOYSA-N 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- 125000005330 8 membered heterocyclic group Chemical group 0.000 description 1
- 239000005660 Abamectin Substances 0.000 description 1
- 239000005875 Acetamiprid Substances 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical class NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 239000005734 Benalaxyl Substances 0.000 description 1
- 241000255789 Bombyx mori Species 0.000 description 1
- 239000005885 Buprofezin Substances 0.000 description 1
- JFLRKDZMHNBDQS-UCQUSYKYSA-N CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C(=C[C@H]3[C@@H]2CC(=O)O1)C)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C.CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C=C[C@H]3C2CC(=O)O1)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C Chemical compound CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C(=C[C@H]3[C@@H]2CC(=O)O1)C)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C.CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C=C[C@H]3C2CC(=O)O1)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C JFLRKDZMHNBDQS-UCQUSYKYSA-N 0.000 description 1
- SERQHEHWRGDMJU-UHFFFAOYSA-N C[SH](C)C(S)=NC(C(Cl)(Cl)Cl)=O Chemical compound C[SH](C)C(S)=NC(C(Cl)(Cl)Cl)=O SERQHEHWRGDMJU-UHFFFAOYSA-N 0.000 description 1
- 239000005745 Captan Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241000887125 Chaptalia nutans Species 0.000 description 1
- 239000005886 Chlorantraniliprole Substances 0.000 description 1
- STUSTWKEFDQFFZ-UHFFFAOYSA-N Chlordimeform Chemical compound CN(C)C=NC1=CC=C(Cl)C=C1C STUSTWKEFDQFFZ-UHFFFAOYSA-N 0.000 description 1
- 239000005747 Chlorothalonil Substances 0.000 description 1
- 239000005945 Chlorpyrifos-methyl Substances 0.000 description 1
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 description 1
- 239000005750 Copper hydroxide Substances 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 239000005889 Cyantraniliprole Substances 0.000 description 1
- 239000005756 Cymoxanil Substances 0.000 description 1
- 239000005946 Cypermethrin Substances 0.000 description 1
- 239000005758 Cyprodinil Substances 0.000 description 1
- 239000005892 Deltamethrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 239000005893 Diflubenzuron Substances 0.000 description 1
- 239000005761 Dimethomorph Substances 0.000 description 1
- AIGRXSNSLVJMEA-UHFFFAOYSA-N EPN Chemical compound C=1C=CC=CC=1P(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 AIGRXSNSLVJMEA-UHFFFAOYSA-N 0.000 description 1
- 240000006890 Erythroxylum coca Species 0.000 description 1
- 239000005896 Etofenprox Substances 0.000 description 1
- 239000005778 Fenpropimorph Substances 0.000 description 1
- 239000005657 Fenpyroximate Substances 0.000 description 1
- 239000005780 Fluazinam Substances 0.000 description 1
- 239000005781 Fludioxonil Substances 0.000 description 1
- 239000005786 Flutolanil Substances 0.000 description 1
- 101100134922 Gallus gallus COR5 gene Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000005907 Indoxacarb Substances 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 239000005867 Iprodione Substances 0.000 description 1
- 239000005797 Iprovalicarb Substances 0.000 description 1
- NWUWYYSKZYIQAE-ZBFHGGJFSA-N L-(R)-iprovalicarb Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)N[C@H](C)C1=CC=C(C)C=C1 NWUWYYSKZYIQAE-ZBFHGGJFSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000218922 Magnoliophyta Species 0.000 description 1
- 235000019759 Maize starch Nutrition 0.000 description 1
- 244000070406 Malus silvestris Species 0.000 description 1
- 239000005805 Mepanipyrim Substances 0.000 description 1
- 239000005807 Metalaxyl Substances 0.000 description 1
- IUOKJNROJISWRO-UHFFFAOYSA-N N-(2-cyano-3-methylbutan-2-yl)-2-(2,4-dichlorophenoxy)propanamide Chemical compound CC(C)C(C)(C#N)NC(=O)C(C)OC1=CC=C(Cl)C=C1Cl IUOKJNROJISWRO-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- HRYILSDLIGTCOP-UHFFFAOYSA-N N-benzoylurea Chemical class NC(=O)NC(=O)C1=CC=CC=C1 HRYILSDLIGTCOP-UHFFFAOYSA-N 0.000 description 1
- 241000358422 Nephotettix cincticeps Species 0.000 description 1
- KYGZCKSPAKDVKC-UHFFFAOYSA-N Oxolinic acid Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC2=C1OCO2 KYGZCKSPAKDVKC-UHFFFAOYSA-N 0.000 description 1
- 239000005813 Penconazole Substances 0.000 description 1
- 239000005816 Penthiopyrad Substances 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 239000005822 Propiconazole Substances 0.000 description 1
- 239000005823 Propineb Substances 0.000 description 1
- 239000005663 Pyridaben Substances 0.000 description 1
- 239000005828 Pyrimethanil Substances 0.000 description 1
- 239000005927 Pyriproxyfen Substances 0.000 description 1
- ISRUGXGCCGIOQO-UHFFFAOYSA-N Rhoden Chemical compound CNC(=O)OC1=CC=CC=C1OC(C)C ISRUGXGCCGIOQO-UHFFFAOYSA-N 0.000 description 1
- 239000005929 Spinetoram Substances 0.000 description 1
- GOENIMGKWNZVDA-OAMCMWGQSA-N Spinetoram Chemical compound CO[C@@H]1[C@H](OCC)[C@@H](OC)[C@H](C)O[C@H]1OC1C[C@H]2[C@@H]3C=C4C(=O)[C@H](C)[C@@H](O[C@@H]5O[C@H](C)[C@H](CC5)N(C)C)CCC[C@H](CC)OC(=O)CC4[C@@H]3CC[C@@H]2C1 GOENIMGKWNZVDA-OAMCMWGQSA-N 0.000 description 1
- 239000005930 Spinosad Substances 0.000 description 1
- 239000005664 Spirodiclofen Substances 0.000 description 1
- 239000005665 Spiromesifen Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229930182692 Strobilurin Natural products 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000005839 Tebuconazole Substances 0.000 description 1
- 239000005658 Tebufenpyrad Substances 0.000 description 1
- 239000005938 Teflubenzuron Substances 0.000 description 1
- 239000005941 Thiamethoxam Substances 0.000 description 1
- 239000005842 Thiophanate-methyl Substances 0.000 description 1
- 239000005857 Trifloxystrobin Substances 0.000 description 1
- 239000005858 Triflumizole Substances 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 229930195482 Validamycin Natural products 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- YASYVMFAVPKPKE-UHFFFAOYSA-N acephate Chemical compound COP(=O)(SC)NC(C)=O YASYVMFAVPKPKE-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- QGLZXHRNAYXIBU-WEVVVXLNSA-N aldicarb Chemical compound CNC(=O)O\N=C\C(C)(C)SC QGLZXHRNAYXIBU-WEVVVXLNSA-N 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000004419 alkynylene group Chemical group 0.000 description 1
- 239000011717 all-trans-retinol Substances 0.000 description 1
- 235000019169 all-trans-retinol Nutrition 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229960002587 amitraz Drugs 0.000 description 1
- QXAITBQSYVNQDR-ZIOPAAQOSA-N amitraz Chemical compound C=1C=C(C)C=C(C)C=1/N=C/N(C)\C=N\C1=CC=C(C)C=C1C QXAITBQSYVNQDR-ZIOPAAQOSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000008059 anilinopyrimidines Chemical class 0.000 description 1
- 229940053200 antiepileptics fatty acid derivative Drugs 0.000 description 1
- 229940058344 antitrematodals organophosphorous compound Drugs 0.000 description 1
- 235000021016 apples Nutrition 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000005667 attractant Substances 0.000 description 1
- RRZXIRBKKLTSOM-XPNPUAGNSA-N avermectin B1a Chemical compound C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 RRZXIRBKKLTSOM-XPNPUAGNSA-N 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- FYZBOYWSHKHDMT-UHFFFAOYSA-N benfuracarb Chemical compound CCOC(=O)CCN(C(C)C)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 FYZBOYWSHKHDMT-UHFFFAOYSA-N 0.000 description 1
- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 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
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- MITFXPHMIHQXPI-UHFFFAOYSA-N benzoxaprofen Natural products N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 229960002903 benzyl benzoate Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- JBLXWRJUHRXORX-UHFFFAOYSA-N bis(methylsulfanyl)methanimine;methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O.CSC(=N)SC JBLXWRJUHRXORX-UHFFFAOYSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- PRLVTUNWOQKEAI-VKAVYKQESA-N buprofezin Chemical compound O=C1N(C(C)C)\C(=N\C(C)(C)C)SCN1C1=CC=CC=C1 PRLVTUNWOQKEAI-VKAVYKQESA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- JHRWWRDRBPCWTF-OLQVQODUSA-N captafol Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)[C@H]21 JHRWWRDRBPCWTF-OLQVQODUSA-N 0.000 description 1
- 229940117949 captan Drugs 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 1
- 229960005286 carbaryl Drugs 0.000 description 1
- 239000006013 carbendazim Substances 0.000 description 1
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- RXDMAYSSBPYBFW-PKFCDNJMSA-N carpropamide Chemical compound N([C@@H](C)C=1C=CC(Cl)=CC=1)C(=O)[C@@]1(CC)[C@H](C)C1(Cl)Cl RXDMAYSSBPYBFW-PKFCDNJMSA-N 0.000 description 1
- IRUJZVNXZWPBMU-UHFFFAOYSA-N cartap Chemical compound NC(=O)SCC(N(C)C)CSC(N)=O IRUJZVNXZWPBMU-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- PSOVNZZNOMJUBI-UHFFFAOYSA-N chlorantraniliprole Chemical compound CNC(=O)C1=CC(Cl)=CC(C)=C1NC(=O)C1=CC(Br)=NN1C1=NC=CC=C1Cl PSOVNZZNOMJUBI-UHFFFAOYSA-N 0.000 description 1
- CWFOCCVIPCEQCK-UHFFFAOYSA-N chlorfenapyr Chemical compound BrC1=C(C(F)(F)F)N(COCC)C(C=2C=CC(Cl)=CC=2)=C1C#N CWFOCCVIPCEQCK-UHFFFAOYSA-N 0.000 description 1
- UISUNVFOGSJSKD-UHFFFAOYSA-N chlorfluazuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC(C=C1Cl)=CC(Cl)=C1OC1=NC=C(C(F)(F)F)C=C1Cl UISUNVFOGSJSKD-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 235000008957 cocaer Nutrition 0.000 description 1
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910001956 copper hydroxide Inorganic materials 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 150000005245 cyanopyrroles Chemical class 0.000 description 1
- DVBUIBGJRQBEDP-UHFFFAOYSA-N cyantraniliprole Chemical compound CNC(=O)C1=CC(C#N)=CC(C)=C1NC(=O)C1=CC(Br)=NN1C1=NC=CC=C1Cl DVBUIBGJRQBEDP-UHFFFAOYSA-N 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- ACMXQHFNODYQAT-UHFFFAOYSA-N cyflufenamid Chemical compound FC1=CC=C(C(F)(F)F)C(C(NOCC2CC2)=NC(=O)CC=2C=CC=CC=2)=C1F ACMXQHFNODYQAT-UHFFFAOYSA-N 0.000 description 1
- 229960005424 cypermethrin Drugs 0.000 description 1
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 description 1
- HAORKNGNJCEJBX-UHFFFAOYSA-N cyprodinil Chemical compound N=1C(C)=CC(C2CC2)=NC=1NC1=CC=CC=C1 HAORKNGNJCEJBX-UHFFFAOYSA-N 0.000 description 1
- 229960002483 decamethrin Drugs 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- OWZREIFADZCYQD-NSHGMRRFSA-N deltamethrin Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OWZREIFADZCYQD-NSHGMRRFSA-N 0.000 description 1
- 230000002951 depilatory effect Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 1
- 150000008056 dicarboxyimides Chemical class 0.000 description 1
- OEBRKCOSUFCWJD-UHFFFAOYSA-N dichlorvos Chemical compound COP(=O)(OC)OC=C(Cl)Cl OEBRKCOSUFCWJD-UHFFFAOYSA-N 0.000 description 1
- 229950001327 dichlorvos Drugs 0.000 description 1
- UOAMTSKGCBMZTC-UHFFFAOYSA-N dicofol Chemical compound C=1C=C(Cl)C=CC=1C(C(Cl)(Cl)Cl)(O)C1=CC=C(Cl)C=C1 UOAMTSKGCBMZTC-UHFFFAOYSA-N 0.000 description 1
- 229940019503 diflubenzuron Drugs 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- YKBZOVFACRVRJN-UHFFFAOYSA-N dinotefuran Chemical compound [O-][N+](=O)\N=C(/NC)NCC1CCOC1 YKBZOVFACRVRJN-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000000967 entomopathogenic effect Effects 0.000 description 1
- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 1
- YREQHYQNNWYQCJ-UHFFFAOYSA-N etofenprox Chemical compound C1=CC(OCC)=CC=C1C(C)(C)COCC1=CC=CC(OC=2C=CC=CC=2)=C1 YREQHYQNNWYQCJ-UHFFFAOYSA-N 0.000 description 1
- 229950005085 etofenprox Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- DIRFUJHNVNOBMY-UHFFFAOYSA-N fenobucarb Chemical compound CCC(C)C1=CC=CC=C1OC(=O)NC DIRFUJHNVNOBMY-UHFFFAOYSA-N 0.000 description 1
- FKLFBQCQQYDUAM-UHFFFAOYSA-N fenpiclonil Chemical compound ClC1=CC=CC(C=2C(=CNC=2)C#N)=C1Cl FKLFBQCQQYDUAM-UHFFFAOYSA-N 0.000 description 1
- YYJNOYZRYGDPNH-MFKUBSTISA-N fenpyroximate Chemical compound C=1C=C(C(=O)OC(C)(C)C)C=CC=1CO/N=C/C=1C(C)=NN(C)C=1OC1=CC=CC=C1 YYJNOYZRYGDPNH-MFKUBSTISA-N 0.000 description 1
- WDQNIWFZKXZFAY-UHFFFAOYSA-M fentin acetate Chemical compound CC([O-])=O.C1=CC=CC=C1[Sn+](C=1C=CC=CC=1)C1=CC=CC=C1 WDQNIWFZKXZFAY-UHFFFAOYSA-M 0.000 description 1
- BFWMWWXRWVJXSE-UHFFFAOYSA-M fentin hydroxide Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(O)C1=CC=CC=C1 BFWMWWXRWVJXSE-UHFFFAOYSA-M 0.000 description 1
- GOWLARCWZRESHU-AQTBWJFISA-N ferimzone Chemical compound C=1C=CC=C(C)C=1C(/C)=N\NC1=NC(C)=CC(C)=N1 GOWLARCWZRESHU-AQTBWJFISA-N 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- UZCGKGPEKUCDTF-UHFFFAOYSA-N fluazinam Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=NC=C(C(F)(F)F)C=C1Cl UZCGKGPEKUCDTF-UHFFFAOYSA-N 0.000 description 1
- MUJOIMFVNIBMKC-UHFFFAOYSA-N fludioxonil Chemical compound C=12OC(F)(F)OC2=CC=CC=1C1=CNC=C1C#N MUJOIMFVNIBMKC-UHFFFAOYSA-N 0.000 description 1
- RYLHNOVXKPXDIP-UHFFFAOYSA-N flufenoxuron Chemical compound C=1C=C(NC(=O)NC(=O)C=2C(=CC=CC=2F)F)C(F)=CC=1OC1=CC=C(C(F)(F)F)C=C1Cl RYLHNOVXKPXDIP-UHFFFAOYSA-N 0.000 description 1
- QOIYTRGFOFZNKF-UHFFFAOYSA-N flupyradifurone Chemical compound C=1C(=O)OCC=1N(CC(F)F)CC1=CC=C(Cl)N=C1 QOIYTRGFOFZNKF-UHFFFAOYSA-N 0.000 description 1
- FQKUGOMFVDPBIZ-UHFFFAOYSA-N flusilazole Chemical compound C=1C=C(F)C=CC=1[Si](C=1C=CC(F)=CC=1)(C)CN1C=NC=N1 FQKUGOMFVDPBIZ-UHFFFAOYSA-N 0.000 description 1
- PTCGDEVVHUXTMP-UHFFFAOYSA-N flutolanil Chemical compound CC(C)OC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1 PTCGDEVVHUXTMP-UHFFFAOYSA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 229940074076 glycerol formal Drugs 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N hexanedioic acid Natural products OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 239000003501 hydroponics Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- KGVPNLBXJKTABS-UHFFFAOYSA-N hymexazol Chemical compound CC1=CC(O)=NO1 KGVPNLBXJKTABS-UHFFFAOYSA-N 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- VBCVPMMZEGZULK-NRFANRHFSA-N indoxacarb Chemical compound C([C@@]1(OC2)C(=O)OC)C3=CC(Cl)=CC=C3C1=NN2C(=O)N(C(=O)OC)C1=CC=C(OC(F)(F)F)C=C1 VBCVPMMZEGZULK-NRFANRHFSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 230000009545 invasion Effects 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- ONUFESLQCSAYKA-UHFFFAOYSA-N iprodione Chemical compound O=C1N(C(=O)NC(C)C)CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 ONUFESLQCSAYKA-UHFFFAOYSA-N 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002545 isoxazoles Chemical class 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 230000000366 juvenile effect Effects 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- PVTHJAPFENJVNC-MHRBZPPQSA-N kasugamycin Chemical compound N[C@H]1C[C@H](NC(=N)C(O)=O)[C@@H](C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O PVTHJAPFENJVNC-MHRBZPPQSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 229920005610 lignin Chemical class 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 1
- 229920000940 maneb Polymers 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- CIFWZNRJIBNXRE-UHFFFAOYSA-N mepanipyrim Chemical compound CC#CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 CIFWZNRJIBNXRE-UHFFFAOYSA-N 0.000 description 1
- BCTQJXQXJVLSIG-UHFFFAOYSA-N mepronil Chemical compound CC(C)OC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C)=C1 BCTQJXQXJVLSIG-UHFFFAOYSA-N 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 229950003442 methoprene Drugs 0.000 description 1
- 229930002897 methoprene Natural products 0.000 description 1
- ZQEIXNIJLIKNTD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-UHFFFAOYSA-N 0.000 description 1
- CJPQIRJHIZUAQP-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(phenylacetyl)alaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)CC1=CC=CC=C1 CJPQIRJHIZUAQP-UHFFFAOYSA-N 0.000 description 1
- CIEXPHRYOLIQQD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-2-furoylalaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)C1=CC=CO1 CIEXPHRYOLIQQD-UHFFFAOYSA-N 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- HIIRDDUVRXCDBN-OBGWFSINSA-N metominostrobin Chemical compound CNC(=O)C(=N\OC)\C1=CC=CC=C1OC1=CC=CC=C1 HIIRDDUVRXCDBN-OBGWFSINSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- FXWHFKOXMBTCMP-WMEDONTMSA-N milbemycin Natural products COC1C2OCC3=C/C=C/C(C)CC(=CCC4CC(CC5(O4)OC(C)C(C)C(OC(=O)C(C)CC(C)C)C5O)OC(=O)C(C=C1C)C23O)C FXWHFKOXMBTCMP-WMEDONTMSA-N 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- HKSZSGAPTPXYTI-UHFFFAOYSA-N n'-[(6-chloropyridin-3-yl)methyl]ethane-1,2-diamine Chemical compound NCCNCC1=CC=C(Cl)N=C1 HKSZSGAPTPXYTI-UHFFFAOYSA-N 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- DSOOGBGKEWZRIH-UHFFFAOYSA-N nereistoxin Chemical class CN(C)C1CSSC1 DSOOGBGKEWZRIH-UHFFFAOYSA-N 0.000 description 1
- 229940079888 nitenpyram Drugs 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- UWVQIROCRJWDKL-UHFFFAOYSA-N oxadixyl Chemical compound CC=1C=CC=C(C)C=1N(C(=O)COC)N1CCOC1=O UWVQIROCRJWDKL-UHFFFAOYSA-N 0.000 description 1
- KZAUOCCYDRDERY-UHFFFAOYSA-N oxamyl Chemical compound CNC(=O)ON=C(SC)C(=O)N(C)C KZAUOCCYDRDERY-UHFFFAOYSA-N 0.000 description 1
- 229960000321 oxolinic acid Drugs 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- LKPLKUMXSAEKID-UHFFFAOYSA-N pentachloronitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LKPLKUMXSAEKID-UHFFFAOYSA-N 0.000 description 1
- 229960000490 permethrin Drugs 0.000 description 1
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical class OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000003016 pheromone Substances 0.000 description 1
- 230000000886 photobiology Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229920001282 polysaccharide Chemical class 0.000 description 1
- 239000005017 polysaccharide Chemical class 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- WHHIPMZEDGBUCC-UHFFFAOYSA-N probenazole Chemical compound C1=CC=C2C(OCC=C)=NS(=O)(=O)C2=C1 WHHIPMZEDGBUCC-UHFFFAOYSA-N 0.000 description 1
- QYMMJNLHFKGANY-UHFFFAOYSA-N profenofos Chemical compound CCCSP(=O)(OCC)OC1=CC=C(Br)C=C1Cl QYMMJNLHFKGANY-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
- KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FITIWKDOCAUBQD-UHFFFAOYSA-N prothiofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(Cl)C=C1Cl FITIWKDOCAUBQD-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- QHGVXILFMXYDRS-UHFFFAOYSA-N pyraclofos Chemical compound C1=C(OP(=O)(OCC)SCCC)C=NN1C1=CC=C(Cl)C=C1 QHGVXILFMXYDRS-UHFFFAOYSA-N 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 description 1
- MIOBBYRMXGNORL-UHFFFAOYSA-N pyrifluquinazon Chemical compound C1C2=CC(C(F)(C(F)(F)F)C(F)(F)F)=CC=C2N(C(=O)C)C(=O)N1NCC1=CC=CN=C1 MIOBBYRMXGNORL-UHFFFAOYSA-N 0.000 description 1
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 1
- ITKAIUGKVKDENI-UHFFFAOYSA-N pyrimidifen Chemical compound CC1=C(C)C(CCOCC)=CC=C1OCCNC1=NC=NC(CC)=C1Cl ITKAIUGKVKDENI-UHFFFAOYSA-N 0.000 description 1
- NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 description 1
- XRJLAOUDSILTFT-UHFFFAOYSA-N pyroquilon Chemical compound O=C1CCC2=CC=CC3=C2N1CC3 XRJLAOUDSILTFT-UHFFFAOYSA-N 0.000 description 1
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000000646 scanning calorimetry Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- HPYNBECUCCGGPA-UHFFFAOYSA-N silafluofen Chemical compound C1=CC(OCC)=CC=C1[Si](C)(C)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 HPYNBECUCCGGPA-UHFFFAOYSA-N 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 229940014213 spinosad Drugs 0.000 description 1
- DTDSAWVUFPGDMX-UHFFFAOYSA-N spirodiclofen Chemical compound CCC(C)(C)C(=O)OC1=C(C=2C(=CC(Cl)=CC=2)Cl)C(=O)OC11CCCCC1 DTDSAWVUFPGDMX-UHFFFAOYSA-N 0.000 description 1
- GOLXNESZZPUPJE-UHFFFAOYSA-N spiromesifen Chemical compound CC1=CC(C)=CC(C)=C1C(C(O1)=O)=C(OC(=O)CC(C)(C)C)C11CCCC1 GOLXNESZZPUPJE-UHFFFAOYSA-N 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 150000003450 sulfenic acids Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- WOSNCVAPUOFXEH-UHFFFAOYSA-N thifluzamide Chemical compound S1C(C)=NC(C(F)(F)F)=C1C(=O)NC1=C(Br)C=C(OC(F)(F)F)C=C1Br WOSNCVAPUOFXEH-UHFFFAOYSA-N 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- VJQYLJSMBWXGDV-UHFFFAOYSA-N tiadinil Chemical compound N1=NSC(C(=O)NC=2C=C(Cl)C(C)=CC=2)=C1C VJQYLJSMBWXGDV-UHFFFAOYSA-N 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical group COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- WPALTCMYPARVNV-UHFFFAOYSA-N tolfenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(OC=3C=CC(C)=CC=3)=CC=2)=C1Cl WPALTCMYPARVNV-UHFFFAOYSA-N 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- A01N47/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing >N—S—C≡(Hal)3 groups
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds
- A01N57/32—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds containing heterocyclic radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C233/05—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C261/00—Derivatives of cyanic acid
- C07C261/04—Cyanamides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/12—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/09—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton the carbon skeleton being further substituted by at least two halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/98—Nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/42—Radicals substituted by singly-bound nitrogen atoms having hetero atoms attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/61—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/08—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/58—Pyridine rings
Abstract
Mevcut buluş, amin türevleriyle ve bunun aynısını kullanan zararlı kontrol ajanları ile ilgilidir.
Description
TEKNIK ALAN
Mevcut bulus, amin türevleriyle ve bunun aynisini kullanan zararli kontrol ajanlari
ile ilgilidir.
TEKNIGIN BILINEN DURUMU
Bugüne kadar birçok zararli kontrol ajani bulunmustur. Bununla birlikte, örnegin
pestisitlere direnç sorunu ve pestisit etkilerinin persistansi ve kullanim aninda
güvenlik gibi endiselerden dolayi bugün halen yeni pestisitlere ihtiyaç
duyulmaktadir.
Patent Disi Doküman 1'de gösterildigi gibi, Dogu Asya ve Özellikle de Güneydogu
Asyaida çeltik kültivasyonunda, imidakloprid gibi neonikotinoidler ve fipronil gibi
fenilpirazol pestisitler dahil olmak üzere baslica insektisitlere kimyasal direnç
gelistirmis olan bitki zararlilarinin verdigi hasar ortaya çikmistir. Sonuç olarak,
direnç gelistirmis olan bitki zararlilari için spesifik ajanlar beklenmektedir.
HeterosikI-içeren amin türevleri ile ilgili olarak, Patent Dokümani 1, nitrojen atomu
üzerinde bir siyano grubuna sahip olan monoalkilamin bilesiklerini ve bu bilesiklerin
yaprak bitleri üzerindeki insektisidal aktivitesini tarif etmektedir. Bununla birlikte, ne
dialkilamin bilesikleri ile ilgili herhangi bir spesifik açiklama yapilmakta, ne de
yaprak bitleri disindaki zararlilar üzerinde kontrol aktivitesinden bahsedilmektedir.
Patent Dokümani 2, bir 2,6-diklor0-4-piridil grubu içeren ve nitrojen atomu üzerinde
bir karboksil grubuna sahip olan amin türevlerinden ve bunlarin fungisidal
aktiviteleri ve insektisidal aktivitelerinden bahsetmekte, fakat baska heterosikliler
ifsa etmemektedir.
Patent Dokümanlari 2 ve 3'te, bir 6-kloro-3-piridil grubu içeren ve nitrojen atomu
üzerinde bir asetil grubuna sahip olan amin türevleri, metabolitler ya da reaksiyon
ara ürünleri olarak ifsa edilmektedir fakat bunlarin zararli kontrol aktivitelerinden
bahsedilmemektedir. Patent Disi Doküman 4, bir 6-kl0ro-3-piridil grubu içeren ve
nitrojen atomu üzerinde bir N-metilkarbamoil grubuna ya da bir N-formilkarbamoil
grubuna sahip olan amin türevlerini ifsa etmektedir, fakat bunlarin zararli kontrol
aktivitelerinden bahsedilmemektedir.
Patent Dokümani 3, formül (Ie)'nin bilesiklerininkine benzer halka yapilarina sahip
olan birden fazla sayida bilesigi ifsa etmektedir, fakat bunlar herbisitler olarak
kullanim için tasarlanmistir; zararli kontrolünden bahsedilmemektedir.
Patent Dokümani 4i N-[1-((6-kloropiridin-3-il)metil)piridin-2(1H)-iliden]- 2,2,2-
trifloroasetamid yapisal formülünü ifsa etmektedir (Patent Dokümani 4'te Tablo 1,
Bilesik No. 3), fakat hazirlama metodu ile ilgili bir seyden bahsedilmemektedir. Bu
bilesik, zararli kontrol aktivitelerinin gözlendigi bilesik listelerinde de
bulunmamaktadir (Patent Dokümani 4'te Tablo 2 ve 3).
trifloroasetamid yapisal formülünü ifsa etmektedir (Patent Dokümani 5'te Tablo 7,
Bilesik No. 12), fakat hazirlama metodu ile ilgili bir seyden bahsedilmemektedir. Bu
bilesikten, çalisma örneklerinde tarif edilen zararli kontrol aktivitelerine sahip olan
bilesiklerin örneklerinde de bahsedilmemektedir.
Patent Disi Doküman 5, sonradan sözü edilen formül (le) bilesiklerine benzer halka
yapilarina sahip olan birden fazla sayida bilesigi ifsa etmektedir, fakat bunlar
yalnizca sentez ara ürünleri olarak ifsa edilmektedir.
Patent Dokümani 6, formül (le)'ye sahip olan bilesiklere benzer halka yapilarina
sahip olan birden fazla sayida bilesigi ifsa etmektedir, fakat bir trifloroasetik asit
imino yapisina sahip olan ilgili bilesiklerden bahsedilmemekte veya
önerilmemektedir.
Alinti Listesi
Patent Literatürleri
26661 A)
Patent Disi Literatürler
BULUSUN KISA AÇIKLAMASI
Bu nedenle mevcut bulusun bir amaci, yeni zararli kontrol ajanlari saglamak ve bu
suretle zararli kontrol alaninda, pestisitlere karsi direnç, pestisit etkilerinin
persistansi ve kullanim aninda güvenlik gibi mevcut pestisitlerdeki sorunlari
çözmektir.
Bulusun baslica bir amaci, kahverengi pirinç zararlisi, beyaz sirtli pirinç zararlisi ve
küçük kahverengi zararliya, çeltik kültivasyonu alaninda günümüzde baslica tüm
böcek zararlilarina karsi kusursuz kontrol etkilerine sahip olan, pestisit dirençli
zararlilara karsi bile yüksek aktiviteye sahip olan ve örnegin topraga uygulama,
tohuma uygulama ve fideye uygulamada kullanim sirasinda isçilerin pestisite maruz
kalma riskini azaltan ve bu nedenle güvenli sekilde kullanilabilen pestisitler
saglamaktir.
Bulus sahipleri, yukaridaki sorunlari çözmek için kapsamli arastirmalar
gerçeklestirmis ve bunun sonucunda, kimyasal formül (l)'e sahip olan amin
türevlerinin zararli kontrol ajanlari olarak kusursuz aktivitelere sahip oldugunu
kesfetmislerdir.
Buna göre mevcut bulus sunlari saglamaktadir:
(1) Bir hayvan disi denekte, bir zararli kontrol ajaninin kullanilmasi adimini
içeren, zararlilarin kontrol edilmesi için bir yöntem, burada söz konusu zararli
kontrol ajani asagidaki formül (l)'in en az bir amin türevini veya bunun bir tuzunu
içermektedir
burada Ar, sübstitüe edilebilen bir fenil grubu ya da sübstitüe edilebilen 5- ya da 6-
üyeli bir heterosikl'dir;
R1 degiskeni bir hidrojen atomu ya da bir CMS alkil grubudur;
R2 degiskeni bir C1-e alkilkarbonil grubu olup, içerisindeki alkil kismi bir halojen
atomu ile sübstitüe edilebilir, bir C1-e alkiloksikarbonil grubu olup, içerisindeki alkil
kismi bir halojen atomu ile sübstitüe edilebilir, bir C1-e alkilsülfonil grubu olup,
içerisindeki alkil kismi bir halojen atomu ile sübstitüe edilebilir, CONR5R7, bir C16
0,0'-alkilfosf0ril grubu olup, içerisindeki alkil kismi bir halojen atomu ile sübstitüe
edilebilir, bir siyano grubu, bir formil grubu ya da bir nitro grubudur;
R3 degiskeni bir halojen atomu ile sübstitüe edilebilen bir C1-8 alkilen grubu, bir
halojen atomu ile sübstitüe edilebilen bir C2-s alkenilen grubu, bir halojen atomu ile
sübstitüe edilebilen bir C2-a alkinilen grubu, sübstitüe edilebilen birfenilen grubu ya
da sübstitüe edilebilen 5- ya da 6- üyeli bir heterosiklik iki degerlikli gruptur; ve
R4 degiskeni bir hidrojen atomu, bir siyano grubu, sübstitüe edilebilen bir fenil
grubu, sübstitüe edilebilen 3- ila 8- üyeli bir siklik alkil grubu, sübstitüe edilebilen 3-
ila 8- üyeli bir heterosiklik, bir halojen atomu, ORs, OCORs, OCOORs, COR5,
CO-NR9R10 ya da S-CS-NRgRio'dur;
burada R5 degiskeni bir halojen atomu ile sübstitüe edilebilen bir 01-5 alkil grubu
atom, bir halojen atomu ile sübstitüe edilebilen bir aril grubu ya da bir halojen atomu
ile sübstitüe edilebilen bir aralkil grubudur;
R6 ve R7 degiskenlerinin her biri bagimsiz olarak bir hidrojen atomu ya da bir halojen
atomu ile sübstitüe edilebilen bir C1-6 alkil grubudur;
Rs degiskeni sübstitüe edilebilen bir C1-6 alkil grubudur, söz konusu sübstitüent bir
halojen atomu, bir 01-4 alkiloksikarbonil grubu, bir C1-4 alkilkarbonil grubu, bir
halojen atomu ile sübstitüe edilebilen bir benzoil grubu ya da bir halojen atomu ile
sübstitüe edilebilen bir Ci-4 alkil grubu, bir 01-4 alkiloksi grubu ya da bir C1-4 alkiltiyo
R9 ve R10 degiskenlerinin her biri bagimsiz olarak bir hidrojen atomu, bir formil
grubu, bir halojen atomu ile sübstitüe edilebilen bir C1.s alkil grubu, içerisinde alkil
kisminin bir halojen atomu ile sübstitüe edilebildigi bir C1-e alkilkarbonil grubu,
içerisinde alkil kisminin bir halojen atomu ile sübstitüe edilebildigi bir C1-6
alkilkarboniloksi grubu, sübstitüe edilebilen bir fenil grubu (söz konusu sübstitüent
bir halojen atomu, bir halojen atomu ile sübstitüe edilebilen bir 01-4 alkil grubu ya
da bir halojen atomu ile sübstitüe edilebilen bir 01-4 alkiloksi grubudur), ya da
sübstitüe edilebilen bir benzil grubudur (söz konusu sübstitüent bir halojen, bir
halojen ile sübstitüe edilebilen bir 01-4 alkil grubu ya da bir halojen ile sübstitüe
edilebilen bir C1-4 alkiloksi grubudur), R9 ve R10 birlikte bir halka olusturur ve en az
bir nitrojen atomu içeren 3- ila 10- üyeli bir heterosikloalkil grubunu gösterir, ya da
N, R9 ve Rio birlikte bir halka olusturur ve en az bir nitrojen atomu içeren 5- ya da
6- üyeli bir aromatik heterosikl grubunu gösterir ve N, R2, R3 ve R4 birlikte formül
(E)”ye sahip olan bir grup olusturabilir:
*15”th
N R4.:
burada Y degiskeni bir hidrojen atomu, bir halojen atomu, bir hidroksil grubu, bir
halojen atomu ile sübstitüe edilebilen bir C1-6 alkil grubu, bir halojen atomu ile
sübstitüe edilebilen bir 0143 alkoksi grubu, bir siyano grubu, bir formil grubu ya da
bir nitro grubudur ve R4e degiskeni bir halojen atomu ile sübstitüe edilmis bir Ci-s
alkil grubu veya bir halojen atomu ile sübstitüe edilebilen bir C1-6 alkoksi grubudur;
yukaridaki durumlar Ar'nin bir 2,6-dikl0r0-4-piridil grubu olmasi durumunda Rzinin
bir C1-6 alkiloksikarbonil grubu olmamasi sartiyla geçerlidir, burada söz konusu alkil
kismi bir halojen atomu ile sübstitüe edilebilir, burada söz konusu amin türevi N-[1-
söz konusu zararli kahverengi kanatli yesil yarimkanatli, pirinç su ekin biti, adzuki
fasulyesi ekin biti, çizgili pire böcegi ve pirinç yaprak bitinden olusan gruptan seçilen
en az bir zararli türüdür.
(2) (1)'e göre yöntem, bitki tohumlari, kökleri, yumrulari, soganlari, rizomlari,
topragi, nütrikültür içerisindeki bir besleyici solüsyonu, nütrikültür içerisindeki bir
kati kültür ortami ya da bitkileri gelistirmek için bir tasiyicinin, böcek kontrol ajani
ile isleme tabi tutulmasini, bu suretle de amin türevinin bitkiler içerisine penetre
edilmesi ve yerlestirilmesi adimini içerir.
(3) Insan veya hayvan vücudunun tedavisi hariç olmak üzere zararlilari kontrol
etmede N-[1-((6-kloropiridin-3-il)metil)piridin-2(1H)-iliden]-2,2,2-trifloroasetamid ve
bunun bir tuzundan seçilen bir amin türevinin kullanimi, burada söz konusu zararli
kahverengi kanatli yesil yarimkanatli, pirinç su ekin biti, adzuki fasulyesi ekin biti,
çizgili pire böcegi ve pirinç yaprak bitinden olusan gruptan seçilen en az bir zararli
Bulusun Avantajli Etkileri
Bulusun amin türevleri kullanilarak, lahana yaprak güvesi, genel tarla kurtlari,
yaprak bitleri, yaprak pireleri, kirpikkanatlilar ve diger birçok zararlinin kontrolünü
etkili bir biçimde gerçeklestirmek mümkündür.
Çizimlerin Kisa Açiklamasi
3-il)metil)piridin-2(1 H)-iliden]-2,2,2-trifloroasetamid kristalleri üzerinde toz x-isini
kirinim analizlerinin sonuçlarini gösteren bir grafiktir.
3-il)metil)piridin-2(1H)-iIiden]-2,2,2-trifloroasetamid kristalleri üzerinde diferansiyel
tarama kalorimetrisi sonuçlarini gösteren bir grafiktir.
piridin-3-il)metil)piridin-2(1 H)-iliden]-2,2,2-trifloroasetamid kristalleri üzerinde toz x-
isini kirinim analizlerinin sonuçlarini gösteren bir grafiktir. [Sek. 4] Sekil 4, ikinci
hazirlama yöntemi vasitasiyla hazirlanan N-[1-((6-kloro- piridin-3-il)metil)piridin-
2(1H)-iliden]-2,2,2-trifl0roasetamid kristalleri üzerinde diferansiyel tarama
kalorimetrisi sonuçlarini gösteren bir grafiktir. [Sek. 5] Sekil 5, üçüncü hazirlama
yöntemi vasitasiyla hazirlanan N-[1-((6-kl0r0- piridin-3-Il)metil)piridin-2(1H)-Iliden]-
2,2,2-trifloroasetamid kristalleri üzerinde diferansiyel tarama kalorimetrisi
sonuçlarini gösteren bir grafiktir.
kloro- piridin-3-il)metil)piridin-2(1 H)-iIiden]-2,2,2-trifl0roasetamid kristalleri
üzerinde toz x-isini kirinim analizlerinin sonuçlarini gösteren bir grafiktir.
piridin-3-il)metil)piridin-2(1H)-iIiden]-2,2,2-trifloroasetamid kristalleri üzerinde
diferansiyel tarama kalorimetrisi sonuçlarini gösteren bir grafiktir. [Sek. 8] Sekil 8,
besinci hazirlama yöntemi vasitasiyla hazirlanan N-[1-((6-kl0r0- piridin-3-
il)metil)piridin-2(1H)-iIiden]-2,2,2-trifloroasetamid kristalleri üzerinde diferansiyel
tarama kalorimetrisi sonuçlarini gösteren bir grafiktir.
BULUSUN DETAYLI AÇIKLAMASI
Yapilandirmalarin Açiklamasi
Bulus tarafindan saglanan zararli kontrol ajanlarinin aktif bilesenleri olarak islev
gören kimyasal formül (l)'in amin türevleri N-[1-((6-kloropiridin-3-il)metil)piridin-
2(1H)-iliden]-2,2,2-trifloroasetamiddir.
Bulusun zararli kontrol ajaninin aktif bileseni olarak islev gören kimyasal formül (l),e
sahip olan bilesik, yaprak uygulamasinda 500 ppm düzeyinde, toprak sulama
uygulamasinda 0.1 mg/fide düzeyinde ve lokal uygulamada 2 mg/böcek düzeyinde
bir kontrol aktivitesine sahip olan (örnegin en az % 30, en az % 50, en az % 80 ya
da % 100 böcek mortalitesi ya da öldürme orani) bir bilesiktir (bulus için test
örneklerine bakin). Alternatif olarak, söz konusu bilesik, böcek motilitesinin
degerlendirilmesi yoluyla belirlenen sekliyle, kök batirma uygulamasi altinda Test
Örnegi 15”te tarif edilen 20 mg/fide düzeyinde ya da kültivasyon kosullari altinda
Test Örnegi 21"e tarif edilen yaklasik 3 ppm düzeyinde bir kontrol aktivitesine
(insektisidal etki) sahip olan bir bilesiktir.
Yapraga uygulamada, söz konusu bilesik daha tercih edilen sekliyle 500 ppm'nin
kontrol aktivitesine sahip olan bir bilesiktir.
Toprak sulama uygulamasinda, söz konusu bilesik daha tercih edilen sekliyle 0.1
mg/fide) bir konsantrasyonda kontrol aktivitesine sahip olan bir bilesiktir.
Lokal uygulamada, söz konusu bilesik daha tercih edilen sekliyle 2 mg/böcek
altinda (örnegin 1 mg/böcek, 0.5 mg/böcek ya da 0.2 mg/böcek) bir
konsantrasyonda bir kontrol aktivitesine sahip olan bir bilesiktir.
Kuru film uygulamasinda, söz konusu bilesik daha tercih edilen sekliyle 200
ppm'nin altinda (örnegin 100 ppm, 50 ppm, 30 ppm, ya da 10 ppm) bir
konsantrasyonda bir kontrol aktivitesine sahip olan bir bilesiktir.
Kök daldirma uygulamasinda, söz konusu bilesik daha tercih edilen sekliyle 20
mg/fide altinda (örnegin 10 mg/fide, 5 mg/fide, 2 mg/fide, 1 mg/fide, 0.5 mg/fide, 0.1
mg/fide, 0.05 mg/fide, 0.03 mg/fide, ya da 0.01 mg/fide) bir konsantrasyonda kontrol
aktivitesine sahip olan bir bilesiktir.
trifloroasetamid, asagidaki fiziksel özelliklere sahiptir. Bu özelliklerden önceki teknik
dokümanlarinin herhangi birinde söz edilmistir.
(a) Toz x-isini kirinim analizinde, söz konusu bilesik en azindan asagidaki kirinim
(b) Diferansiyel tarama kalorimetrisinde (DSC), söz konusu bilesik 155 ila 158°C'lik
bir erime noktasi sergiler.
Kimyasal formül (I)”e sahip olan bulus bilesiklerinden en az birini içeren zararli
kontrol ajanlarinin kontrol etkileri sergiledigi zararli türü kahverengi kanatli yesil
yarimkanatli, pirinç su ekin biti, adzuki fasulyesi ekin biti, çizgili pire böcegi ve pirinç
yaprak bitinden olusan gruptan seçilen en az bir zararli türüdür.
Mevcut bulus tarafindan saglanan zararli kontrol ajanlari tarimsal ve bahçecilikte
kullanim için insektisitler, hayvan içi parazitler için kontrol ajanlari, hayvan disi
parazitler Için kontrol ajanlari, sihhi zararlilar için kontrol ajanlari, rahatsiz edici
zararlilar için kontrol ajanlari, saklanan tahil/saklanan gida zararlilar için kontrol
ajanlari ve hanelerdeki zararlilar için kontrol ajanlari olarak örneklendirilmektedir.
Tarimsal ve bahçecilikte kullanim Için insektisitler, hayvan için parazitler için kontrol
ajanlari ve hayvan disi parazitler için kontrol ajanlari tercih edilmektedir.
Bulusun zararli kontrol ajanlari, kimyasal formül (l)'e sahip olan bir bilesik disinda,
planlanan kullanim yöntemine uygun bir tasiyici kullanarak hazirlanabilir.
Bulusun zararli kontrol ajani tarimsal bir zararli kontrol ajani oldugu zaman, aktif
bilesen genel olarak uygun bir kati tasiyici, sivi tasiyici, gaz halinde tasiyici, yüzey
aktif madde, dispersan ve baska adjuvanlar ile karistirilir ve söz konusu ajan
emülsiyon haline getirilebilen bir konsantre, sivi formülasyon, süspansiyon
konsantresi, sulandirilabilir toz, akici konsantre, toz, granüller, tabletler, yag
solüsyonu, aerosol ya da dumanlama ajani gibi istenen herhangi bir formda
Kati tasiyicilarin örnekleri talk, bentonit, kil, kaolin, kizelgur, vermikulit, beyaz
karbon ve kalsiyum karbonati kapsamaktadir.
Sivi tasiyicilarin örnekleri metanol, n-heksanol ve etilen glikol gibi alkolleri, aseton,
metil etil keton ve sikloheksanon gibi ketonlari, n-heksan ve ketosen gibi alifatik
hidrokarbonlari, tolüen, ksilen ve metil naftalen gibi aromatik hidrokarbonlari, dietil
eter, dioksan ve Ietrahidrofuran gibi eterleri, etil asetat gibi esterleri, asetonitril ve
izobütironitril gibi nitrilleri, dimetilformamid ve dimetilasetamid gibi asit amidleri,
soya yagi ve pamuk tohumu yagi gibi nebati yaglari, dimetil sülfoksit ve suyu
kapsamaktadir.
Gaz halinde tasiyicilarin örnekleri sivi propan gazi, hava, nitrojen, karbon dioksit
ve dimetil eteri kapsamaktadir.
Emülsifikasyon, dispersiyon, yayma, yapistirma ve benzeri amaçla kullanilabilen
yüzey aktif maddeler ve dispersanlar alkilsülfürik asit esterleri, alkil(aril)sülf0nikasit
tuzlarini, polioksialkilen alkil(aril) eterleri, poliol esterleri ve Iigninsülfonik asit
tuzlarini kapsamaktadir.
Formülasyonun özelliklerini gelistirmek için kullanilabilen adjuvanlar
karboksimetilselüloz, arap sakizi, polietilen glikol ve kalsiyum stearati
kapsamaktadir.
Yukaridaki tasiyicilar, yüzey aktif maddeler, dispersanlar ve adjuvanlarin her biri
gerektigi sekilde tek basina ya da kombinasyon halinde kullanilabilir.
Yukaridaki formülasyon içerisinde aktif bilesen içerigi, belirli bir biçimde
kisitlanmamakla birlikte, emülsiyon haline getirilebilir konsantreler içerisinde
agirlikça % 1 ila 75 arasinda, tozlar içerisinde agirlikça % 0.3 ila 25 arasinda,
sulandirilabilir tozlar içerisinde agirlikça % 1 ila 90 arasinda ve granüller içerisinde
Kimyasal formül (l)”e sahip olan bilesikler, bu bilesikleri içeren formülasyonlar ve
bunlarin diger zararli kontrol ajanlari ile karisimlari uygun bir biçimde örnegin böcek
zararlilarina, bitkilere, bitki çogaltma materyallerine (örnegin tohumlar, bitki
yapraklari, kökler, çimlenmis bitkiler ve fideler), toprak, topraksiz bitki yetistirmede
kullanilan besleyici solüsyonlar, topraksiz bitki yetistirmede kullanilan kati ortamlar
ya da zararlilar tarafindan istilayi önlemek için ihtiyaç duyulan mekanlara
uygulanabilir. Bu uygulamaya tabi tutulan bitkiler genetik olarak modifiye edilmis
ürünleri kapsamaktadir.
Bu uygulama zararli Istilasindan önce ve sonra gerçeklestirilebilir.
Özellikle, tohumlar, kökler, yumrular, soganlar, rizomlar, çimlenmis bitkiler, fideler,
topraklar, topraksiz bitki yetistirmede kullanilan besleyici solüsyonlar ve topraksiz
bitki yetistirmede kullanilan kati ortamlardan olusan gruptan seçilen bir hedefe etkili
bir dozda uygulanan ve böylelikle bitki içerisinde penetre olmasi ve yerlesmesi
saglanan amin türevleri, bunlari içeren formülasyonlar ve bunlarin baska zararli
kontrol ajanlari ile kombinasyonlari zararlilari kontrol edebilir.
Yukaridaki uygulama hedeflerinin bitki tohumlari, kökleri, yumrulari, soganlari ya da
rizomlari oldugu durumlarda, tercih edilen uygulama yöntemi örnekleri,
penetrasyon ve translokasyon engellenmedigi sürece belirli bir sekilde
kisitlanmamaktadir ve örnegin sulama yöntemleri, toz kaplama yöntemleri, sivama
yöntemleri, püskürtme yöntemleri, pellet yöntemleri ve film kaplama yöntemlerini
kapsamaktadir.
Tohumlar olmasi durumunda, uygulama yönteminin örnekleri daldirma, toz
kaplama, sivama, püskürtme, pellet uygulama, film kaplama ve fumigasyonu
kapsamaktadir. Daldirma, tohumlari zararli kontrol ajaninin bir sivi solüsyonu
içerisine batirma yöntemidir. Toz kaplama yöntemleri, toz haline getirilmis formda
zararli kontrol ajaninin kuru tohumlar üzerine kaplanmasini kapsayan kuru toz
kaplama ve toz haline getirilmis formda zararli kontrol ajaninin hafif sulu-nemli
tohumlar üzerine kaplanmasini kapsayan sulu toz kaplamayi kapsamaktadir. Diger
yöntemler, süspansiyon haline getirilmis bir formda zararli kontrol ajaninin bir
mikser içerisinde tohumlarin yüzeyine uygulanmasi için bir sivama yöntemi ve
bunun tohumlarin yüzeyi üzerine püskürtülmesi için bir püskürtme yöntemidir. Diger
uygulama yöntemleri, tohumlar belirli bir büyüklük ve sekle sahip olan pelletler
içerisinde bir dolgu maddesi ile birlikte olusturuldugu zaman uygulamanin dolgu
maddesi ile zararli kontrol ajaninin karistirilmasi yoluyla gerçeklestirildigi bir pellet
yöntemini; tohumlarin zararli kontrol ajanini içeren bir filmle kaplanmasini
gerektiren bir film kaplama yöntemini; ve kapali bir kap içerisinde gaz haline
getirilen zararli kontrol ajaniyla tohumlarin dezenfeksiyonunu gerektiren bir
fumigasyon yöntemini kapsamaktadir.
Çimlenmis bitkilere ve fidelere uygulama durumunda, bu bitkiler, çimlenmeyi
takiben ve topraktan çikisini takiben, fakat transplantasyondan önce, daldirma
yoluyla sistemik veya kismi uygulama vasitasiyla uygulama yoluyla korunabilir.
Tohumlara, köklere, yumrulara, soganlara ya da rizomlara uygulama durumunda,
baska bir etmen tohumlarin, köklerin, yumrularin, soganlarin ya da rizomlarin
zararli kontrol ajaninin penetrasyonuna ve translokasyonuna olanak veren yeterli
bir süre boyunca daldirilmasidir. Böyle bir durumda, daldirmanin gerçeklestirildigi
süre ve sicaklik, uygulamanin hedefi ve kimyasalin türü ve dozuna uygun olarak
teknikte uzman olan bir kimsece uygun sekilde belirlenebilir. Ek olarak, penetrasyon
ve translokasyon süresi belirli herhangi bir kisitlamaya tabi degildir ve örnegin 1
saat ya da daha fazla olabilir. Penetrasyon ve translokasyon sirasinda sicaklik
örnegin 5 ila 45°C'dir.
Topraga uygulama yöntemlerinin örnekleri bulus bilesiginin, bunlari içeren
formülasyonlarin ya da bunlarin baska zararli kontrol ajanlari ile karisimlarinin
granüllerinin toprak içerisine ya da toprak üzerine uygulanmasidir. Tercih edilen
toprak uygulama yöntemleri püskürtme, bant uygulama, karik uygulama ve dikim
deligi uygulamasidir. Burada, püskürtme uygulamasi, tedavi edilecek olan tüm
yüzey alani üzerinden yüzey uygulamasidir ve sonradan toprak içerisine mekanik
uygulamayi kapsamaktadir.
Toprak tedavisinin diger bir kullanisli yöntemi, su içerisinde emülsiyon haline
getirilmis ya da çözündürülmüs bulus bilesiklerinin, bunlari içeren bir formülasyonun
ya da bunlarin baska bir zararli kontrol ajani ile bir karisiminin bir solüsyonu ile
topragin islatilmasi yoluyla uygulamayi kapsamaktadir.
Kati ortam kültivasyonu, örnegin topraksiz bitki yetistirme, kum kültürü, besleyici
film teknigi (NFT) ve tas yünü teknigi gibi sebzeler ve çiçekli bitkilerin üretimi için
nutrikültürel sistemler içerisinde besleyici solüsyonlara uygulama durumunda,
bulus bilesikleri ya da bunlari içeren formülasyonlar ya da bunlarin baska zararli
kontrol ajanlari ile karisimlarinin, vermikülit içeren suni bir bitki gelisme ortamina ya
da fideleri yetistirmek için suni bir mat içeren bir kati ortama dogrudan
uygulanabildigi açiktir.
Yukaridaki uygulama adiminda, amin türevlerinin etkili dozu tercih edilen sekliyle
formül (1) ya da formül (1e)'ye sahip olan bilesik için sonraki penetrasyon ve
translokasyon adiminda penetre olmak ve yerlestirmek için yeterli bir miktardir.
Bu etkili doza, bilesigin özellikleri, uygulama hedefinin türü ve miktari, sonraki
penetrasyon ve translokasyon adiminin uzunlugu ve sicaklik gibi etmenler dikkate
alinarak uygun sekilde karar verilebilir. Örnegin, tohumlara uygulama durumunda,
amin türevlerinin dozu tercih edilen sekliyle her 10 kg tohum basina 1 9 ila 10 kg ve
daha tercih edilen sekliyle 10 9 ila 1 kg arasindadir. Topraga uygulama durumunda,
amin türevlerinin dozu tercih edilen sekliyle kültive edilen topragin her 10 ari basina
0.1 9 ila 10 kg ve daha tercih edilen sekliyle 1 9 ila 10 kg arasindadir. Bitkilere
yaprak uygulamasi durumunda, amin türevlerinin dozu tercih edilen sekliyle kültive
edilen topragin her 10 ari basina 0.1 g ila 10 kg ve daha tercih edilen sekliyle 1 9
ila 1 kg arasindadir.
Bulusun zararli kontrol ajaninin hayvan parazitik zararlilarini kontrol etmek için bir
ajan oldugu durumlarda, örnegin bir sivi formülasyon, bir emülsiyon haline
getirilebilir konsantre, sivilastirilmis damla formülasyonu, bir sprey, bir köpük
formülasyonu, tabletler, granüller, ince granüller, bir toz, kapsüller, tabletler,
çignenebilir bir preparasyon, bir enjeksiyon, bir supozituvar, bir krem, bir sampuan,
bir durulama, bir reçine formülasyonu, bir dumanlama ajani ya da zehirli yem olarak
sunulabilir. Sivi birformülasyon ya da damla için sivi birformülasyon olarak sunum
Sivi formülasyonlarda genel emülsiyon haline getirici ajanlar, dispersanlar,
serpiciler, sulandirma ajanlari, süspansiyon haline getirici ajanlar, koruyucular ve
iticiler gibi adjuvanlar da dahil edilebilir ve bunlara ek olarak alisildik film Olusturucu
ajanlar da dahil edilebilir. Emülsifikasyon, dispersiyon, serpme, yapistirma ve
benzeri için kullanilabilen yüzey aktif maddeler sabunlari, polioksialkilen alkil(aril)
eterleri, polioksietilen alkilallil eterleri, polioksietilen yag asidi esterleri, yüksek
alkolleri ve alkil aril sülfonatlari kapsamaktadir. Dispersanlarin örnekleri kazein,
jelatin, polisakkaritler, lignin türevleri, sekerler ve sentetik suda çözünebilir
polimerleri kapsamaktadir. Serpme ve sulandirma ajanlarinin örnekleri gliserol ve
polietilen glikolü kapsamaktadir. Süspansiyon haline getirici ajanlarin örnekleri
kazein, jelatin, hidroksipropil selüloz ve arap sakizini kapsamaktadir. Stabilizörlerin
örnekleri fenol bazli antioksidanlari (örnegin BHT, BHA), amin bazli antioksidanlari
(örnegin difenilamin) ve ogranosülfür bazli antioksidanlari kapsamaktadir.
Koruyucularin örnekleri metil p-oksibenzoat, etil p-oksibenzoat, propil p-
oksibenzoat ve bütil p-oksibenzoati kapsamaktadir. Yukaridaki tasiyicilar, yüzey
aktif maddeler, dispersanlar ve adjuvanlarin her biri gerektigi sekilde tek basina ya
da kombinasyon halinde kullanilabilir. Ek olarak, kokular ve sinerjistler de dahil
edilebilir. Sivi bir formülasyonda, bulusun zararli kontrol ajanlarinda aktif bilesenin
içeriginin genel olarak agirlikça % 1 ila 75 olmasi uygundur.
Bir krem formülasyonu hazirlamak için kullanilan tasiyicilarin örnekleri uçucu
olmayan hidrokarbonlar (örnegin sivi parafin), su ve yag eklenen lanolin yaglari,
yüksek yag asitleri, yag asit esterleri, nebati yaglar, silikon yaglari ve sudur. Ek
olarak, emülsiyon haline getirici ajanlar, nemlendiriciler, antioksidanlar, kokular,
boraks ve ultraviyole emicilerin her biri gerektigi sekilde tek basina ya da
kombinasyon halinde kullanilabilir. Emülsiyon haline getirici ajanlarin örnekleri yag
asit sorbitanlari, polioksietilen alkil eterler ve yag asit polioksietilenleri
kapsamaktadir. Bulusun zararli kontrol ajani içerisindeki aktif bilesen içeriginin
krem formülasyonlarinda agirlikça % 0.5 ila 70 olmasi uygundur.
Kapsüller, haplar ya da tabletler olmasi durumunda, bulus kompozisyonu
içerisindeki aktif bilesen uygun bir biçimde bölünür ve nisasta, Iaktoz ya da talk gibi
bir tasiyici ya da bir seyreltme sivisi ile karistirilir, buna ilave olarak magnezyum
stearat gibi bir dezentegran ve/veya bir baglayici eklenir. Gerekli olmasi halinde,
formülasyon kullanimdan önce tablet haline getirilebilir.
Enjeksiyon olmasi durumunda, preparasyon steril bir solüsyon olarak
gerçeklestirilebilir. Enjeksiyon, solüsyonu kanla izotonik hale getirmek için yeterli
tuz ya da glikoz içerebilir. Enjeksiyonu hazirlamak için kullanilabilen tasiyicilarin
örnekleri gliseritler, benzil benzoat, izopropil miristat, propilen glikolün ve diger
esterlerin yag asidi türevleri ve N-metilpirrolidon ve gliserol formal gibi organik
solventleri kapsamaktadir. Bulusun zararli kontrol ajani içerisindeki aktif bilesen
içeriginin enjeksiyonlarda agirlikça % 0.01 ila 10 olmasi uygundur.
Bir reçine formülasyonu hazirlamak için tasiyicilarin örnekleri vinil klorür bazli
polimerleri ve poliüretani kapsamaktadir. Gerekli olmasi halinde, bu formülasyonlar
için baz olarak fitalik asit ester, adipik asit ester ya da stearik asit gibi bir
plastiklestirici eklenebilir. Aktif bilesen bu baz içerisinde yogrulduktan sonra, reçine
formülasyonu enjeksiyon kaliplama, ekstrüzyon ya da basinç altinda kaliplama
yoluyla sekillendirilir. Ek olarak, kaliplama ve kesme gibi adimlardan geçirilerek,
formülasyon hayvanlar için kulak künyeleri ve hayvanlar için zararli kontrol
tasmalari haline getirilebilir.
Zehirli yem için tasiyici örnekleri besin maddeleri ve atraktanlari (örnegin tahil
unlari, örnegin bugday unu ve misir unu, nisastalar, örnegin misir nisastasi ve
patates nisastasi, sekerler, örnegin granüler seker, arpa malti ve bal, tatlandiricilar,
örnegin gliserol, sogan çesnisi ve süt çesnisi, hayvan esasli tozlar, örnegin
ipekböcegi tozu ve balik tozu ve çesitli feromonlari) kapsamaktadir. Bulusun zararli
kontrol ajani içerisindeki aktif bilesen içeriginin zehirli yem içerisinde agirlikça genel
olarak % 0.001 ila 90 olmasi uygundur.
Zararli kontrolü, hedef hayvanin vücudu içerisinde bulusun zararli kontrol ajaninin
oral olarak ya da enjeksiyon yoluyla uygulanmasi veya bulusun zararli kontrol
ajaninin hedef hayvanin vücut yüzeyinin tamami veya bir kismina uygulanmasi
yoluyla gerçeklestirilebilir. Alternatif olarak, zararli kontrolü ayni zamanda
zararlilarin istila etmesi, yayilmasi veya hareket etmesi beklenen yerlerin bulusun
zararli kontrol ajani ile kaplanmasi yoluyla da gerçeklestirilebilir.
Bulusun zararli kontrol ajani dogrudan oldugu gibi kullanilabilir veya, belirli duruma
bagli olarak su, sivi bir tasiyici ile seyrelttikten sonra ya da ticari bir sampuan,
durulama, besin veya hayvan tarhi ile uygulanabilir.
Ayni zamanda, bu ulusa göre zararli kontrol ajanlari fungisitler, insektisitler,
akarisitler, herbisitler, bitki büyüme düzenleyicileri ve gübreler gibi baska
kimyasallarla karisim halinde kullanilabilir. Karisimda kullanilabilen kimyasallar
Pestisit Kilavuzunda (The British Crop Protection Council yayini, 13. basim) ve
Shibuya Indeksinde (Shibuya Index Research Group yayini, 13. Basim, 2008)
sayilan bilesikleri kapsamaktadir. Insektisitler, akarisitler ve nematisitlerin spesifik
örnekleri organofosfat bilesikleri, örnegin asefat, diklorvos, EPN, fenitiyon,
fenamifos, protiyofos, profenofos, piraklofos, klorpirifos-metil, diazinon, fostiyazat
ve imisiyafos; karbamat bilesikleri, örnegin metomil, tiyodikarb, aldikarb, oksamil,
propoksur, karbaril, fenobukarb, etiyofenkarb, fenotiyokarb, pirimikarb, karbofuran
ve benfurakarb; nereistoksin türevleri, örnegin kartap ve tiyosikla; organo-klor
bilesikleri örnegin dikofol ve tetradifon; piretroid bilesikleri örnegin permetrin,
terflutrin, sipermetrin, deltametrin, siyalotrin, fenvalerat, fluvilanat, etofenproks ve
silafluofen; benzoil üre bilesikleri, örnegin diflubenzuron, teflubenzuron,
flufenoksuron ve klorfluazuron; jüvenil hormon benzeri bilesikler, örnegin metopren;
ve tüy dökücü homon benzer bilesikler, örnegin kromafenozidi kapsamaktadir.
Diger bilesiklerin örnekleri buprofezin, heksitiazoks, amitraz, klordimeform,
piridaben, fenpiroksimat, pirimidifen, tebufenpirad, tolfenpirad, fluakripirim,
asekuinosil, siflumetofen, flubendizmid, etiprol, fipronil, etoksazle, imidakloprid,
klotianidin, tiametoksam, asetamiprid, nitenpiram, tiazkloprid, dinotefuran,
pimetrozin, bifenazat, spirodiklofen, spiromesifen, flonisamid, klorfenapir,
piriproksifen, indoksakarb, piridalil, spinosad, avermektin, milbemisin, sineopirafen,
spinetoram, piriflukuinazon, klorantraniliprol, siyantraniliprol, spirotetramat,
sulfoksaflor, flupiradifuron, flometokuin, organometalik bilesikler, dinitro bilesikleri,
organosülfür bilesikleri, üre bilesikleri, triazin bilesikleri ve hidrazin bilesiklerini
kapsamaktadir.
Bulusun zararli kontrol ajanlari ayni zamanda BT formülasyonlari ve
entomopatojenik virüs formülasyonlari gibi mikrobiyal pestisitlerle karisim halinde
Karisim halinde veya bir arada kullanilabilen fungisitlerin örnekleri strobilurin
bilesiklerini, örnegin asazoksistrobin, kresoksim-metil, trifloksistrobin,
metominostrobin ve orisastrobin; anilinopirimidin bilesiklerini, örnegin mepanipirim,
pirimetanil ve siprodinil; azol bilesiklerini, örnegin triadimefon, bitertanol, triflumizol,
metokonazol, propikonazol, penkonazol, flusilazol, miklobütanil, siprokonazol,
tebukonazol, heksakonazol, prokloraz ve simekonazol; kuinoksalin bilesiklerini,
örnegin kuinometiyonat; ditiyokarbamat bilesiklerini, örnegin maneb, zineb,
mankozeb, polikarbamat ve propineb; fenilkarbamat bilesiklerini, örnegin
dietofenkarb; organoklorin bilesiklerini, örnegin klorothalonil ve kuintozen;
benzimidazol bilesiklerini, örnegin benomil, tiyofanat-metil ve karbendazol;
fenilamid bilesiklerini, örnegin metalaksil, oksadiksil, ofuraz, benalaksil, furalaksil
ve siprofuram; sulfenik asit bilesiklerini, örnegin asdiklofluanid; bakir bilesiklerini,
örnegin bakir hidroksit ve oksin-bakir; izoksazol bilesiklerini, örnegin
hidroksiizoksazol; organofosforöz bilesikleri, örnegin fosetiI-alüminyum ve tolklofos-
metil; N-halojenotiyoalkil bilesiklerini, örnegin kaptan, kaptafol ve folfet;
dikarboksimid bilesiklerini, örnegin prosimidon, iprodion ve vinklozin; karboksianilid
bilesiklerini, örnegin flutolanil, mepronil, furamepir, tifluzamid, boskalid ve
pentiopirad; morfolin bilesiklerini, örnegin fenpropimorf ve dimetomorf; organotin
bilesiklerini, örnegin fentin hidroksit ve fentin asetat; siyanopirrol bilesiklerini,
örnegin fludioksonil ve fenpiklonil; ve ayni zamanda trisiklazol, pirokuilon,
karpropamid, diklosimet, fenoksanil, fthalojenür, fluazinam, simoksanil, triforin,
pirifenoks, fenarimol, fenpropidin, pensikuron, ferimzon, siyazofamid, iprovalikarb,
bentiavalikarb-izopropil, iminoktadin-albesilat, siflufenamid, kasugamisin,
validamisin, streptomsin, oksolinik asit, tebuflokuin, probenazol, tiadinil ve isotiyanili
kapsamaktadir.
Bulus Bilesiklerini Sentezlemek için Yöntemler Kimyasal formül (Ie)'ye sahip olan
bir bilesik olup:
burada Ar, R1, Y ve R4e yukarida tanimlandigi gibidir ve bilesik asagidaki formül
(lX)'a sahip olan bir bilesigin, bir bazin varliginda ya da yoklugunda, formül
ArCH(R1)X'e (burada Ar ve R1 yukarida tanimlandigi gibidir ve X degiskeni bir
halojen, OTs ya da OMsidir) sahip olan bir bilesikle reaksiyona sokulmasi yoluyla
elde edilebilir.
(Reaksiyonda, Y ve R4e yukarida tanimlandigi gibidir.
Reaksiyon bir bazin varliginda gerçeklestirildigi zaman, söz konusu baz örnegin
sodyum hidrit gibi bir alkali metal hidrit, potasyum karbonat ya da sodyum karbonat
gibi bir karbonat, potasyum hidroksit ya da sodyum hidroksit gibi bir alkali metal
hidroksit, trietilamin gibi bir tersiyer amin ya da piridin veya 4-dimetilaminopiridin
gibi sübstitüe edilmis ya da edilmemis bir piridin bilesigi olabilir.
Reaksiyon bir solventin yoklugunda ya da reaksiyonu etkilemeyen bir solvent
kullanarak gerçeklestirilebilir. Bir solventin kullanildigi durumlarda, amidler (örnegin
dimetilformamid, dimetilasetamid), nitriller (örnegin asetonitril), sülfoksitler (örnegin
dimetilsülfoksit), eterler (örnegin dietil eter. tetrahidrofuran), esterler (örnegin etil
asetat, bütil asetat), aromatik hidrokarbonlar (örnegin benzen, ksilen, tolüen),
alkoller (örnegin metanol, etanol, propanol), ketonlar (örnegin aseton, metil etil
keton), alifatik hidrokarbonlar (örnegin heksan, heptan, oktan), ya da halojenlenmis
hidrokarbonlar (örnegin diklorometan, kloroform, klorobenzen, diklorobenzen) gibi
solventler tek basina ya da iki veya daha fazlasinin kombinasyonlari olarak
kullanilabilir. Asetonitril kullanilmasi tercih edilmektedir.
Reaksiyon, genel olarak 0 ila 200°C arasinda gerçeklestirilebilir, bununla birlikte
ayiracin 20 ila 40°C'de eklenmesi ve reaksiyonun 60 ila 80°C'de gerçeklestirilmesi
tercih edilmektedir.
Yukaridaki kimyasal formül (IX)'a sahip olan bilesikler, R4e-C (=O)X, R4e-
C(=O)OC(=O)R4, ya da R4eC(=O)OR' (burada X degiskeni bir halojen atomu. OTs
ya da Oms'dir; R' degiskeni bir C1-6 alkil grubudur; ve R4e degiskeni yukarida
tanimlandigi gibidir) formülüne sahip olan bir bilesigin, bir bazin varliginda ya da
yoklugunda asagidaki formül (IXa)”ya sahip olan bir bilesikle reaksiyon sokulmasi
yoluyla elde edilebilir.
Formülde, Y degiskeni yukarida tanimlandigi gibidir.
Reaksiyon bir bazin varliginda gerçeklestirildigi zaman, söz konusu baz örnegin
sodyum hidrit gibi bir alkali metal hidrit, potasyum karbonat ya da sodyum karbonat
gibi bir karbonat, potasyum hidroksit ya da sodyum hidroksit gibi bir alkali metal
hidroksit, trietilamin gibi bir tersiyer amin ya da piridin veya 4-dimetilaminopiridin
gibi sübstitüe edilmis ya da edilmemis bir piridin bilesigi olabilir.
Reaksiyon bir solventin yoklugunda ya da reaksiyonu etkilemeyen bir solvent
kullanarak gerçeklestirilebilir. Bir solventin kullanildigi durumlarda, amidler (örnegin
dimetilformamid, dimetilasetamid), nitriller (örnegin asetonitril), sülfoksitler (örnegin
dimetilsülfoksit), eterler (örnegin dietil eter, tetrahidrofuran), esterler (örnegin etil
asetat, bütil asetat), aromatik hidrokarbonlar (örnegin benzen, ksilen, tolüen),
alkoller (örnegin metanol, etanol, propanol), ketonlar (örnegin aseton, metil etil
keton), alifatik hidrokarbonlar (örnegin heksan, heptan, oktan), ya da halojenlenmis
hidrokarbonlar (örnegin diklorometan, kloroform, klorobenzen, diklorobenzen) gibi
solventler ya da su tek basina ya da iki veya daha fazlasinin kombinasyonlari olarak
kullanilabilir. Dimetilformamid, asetonitril, eterler, diklorometan ya da kloroform
kullanilmasi tercih edilmektedir.
Reaksiyon, genel olarak -80 ila 100°C arasinda gerçeklestirilebilir, bununla birlikte
reaksiyonun 20 ila 50°C araliginda gerçeklestirilmesi tercih edilmektedir.
Yukaridaki formül (lX)'a sahip bilesik ayni zamanda yukaridaki formül (IXa)*ya sahip
olan bir bilesigin, bir bazin varliginda ya da yoklugunda bir dehidrasyon-
kondansasyon ajani kullanarak R4e-COOH formülüne (burada R4e degiskeni
yukarida tanimlandigi gibidir) sahip olan bir karboksilik asitle reaksiyona sokulmasi
yoluyla elde edilebilir.
Disikloheksilkarbodiimid ya da 1-etiI-3-(3-dimetilaminopropil)karb0diimid
hidroklorür gibi bir karbodiimid bilesigi, dehidrasyon-kondansasyon ajani olarak
kullanilabilir.
Reaksiyon bir bazin varliginda gerçeklestirildigi zaman, söz konusu baz örnegin
potasyum karbonat ya da sodyum karbonat gibi bir karbonat, trietilamin gibi bir
tersiyer amin ya da piridin veya 4-dimetilamin0piridin gibi sübstitüe edilmis ya da
edilmemis bir piridin bilesigi olabilir.
Söz konusu reaksiyon tercih edilen sekliyle bir solvent kullanarak gerçeklestirilir.
Örnegin amidler (örnegin dimetilformamid, dimetilasetamid), nitriller (örnegin
asetonitril), sülfoksitler (örnegin dimetilsülfoksit), eterler (örnegin dietil eter,
tetrahidrofuran), esterler (örnegin etil asetat, bütil asetat), aromatik hidrokarbonlar
(örnegin benzen, ksilen, tolüen), ketonlar (örnegin aseton, metil etil keton), alifatik
hidrokarbonlar (örnegin heksan, heptan, oktan), ya da halojenlenmis hidrokarbonlar
(örnegin diklorometan, kloroform, klorobenzen, diklorobenzen) tek basina ya da iki
veya daha fazlasinin kombinasyonlari olarak kullanilabilir. Diklorometan ya da
kloroform kullanilmasi tercih edilmektedir.
Reaksiyon, genel olarak -80 ila 100°C arasinda gerçeklestirilebilir, bununla birlikte
reaksiyonun 20 ila 50°C araliginda gerçeklestirilmesi tercih edilmektedir.
Yukaridaki formül (Ie)'ye sahip olan bilesikler, bir bazin varliginda ya da
yoklugunda, formül R4e-C(=O)X, R4e-C(=O)OC(=O)R4e ya da R4e-C(=O)OR
formülüne (burada X degiskeni bir halojen atomudur, R' degiskeni bir C1-6 alkil
grubudur ve R4e degiskeni yukarida tanimlandigi gibidir) sahip olan bir bilesigin
asagidaki formül (IXb)'ye sahip olan bir bilesik ya da bunun bir tuzuyla reaksiyona
sokulmasi yoluyla elde edilebilir.
(Formülde, Ar, R1 ve Y degiskenleri yukarida tanimlandigi gibidir.
Reaksiyon bir bazin varliginda gerçeklestirildigi zaman, söz konusu baz örnegin
sodyum hidrit gibi bir alkali metal hidrit, potasyum karbonat ya da sodyum karbonat
gibi bir karbonat, potasyum hidroksit ya da sodyum hidroksit gibi bir alkali metal
hidroksit, trietilamin gibi bir tersiyer amin ya da piridin veya 4-dimetilaminopiridin
gibi sübstitüe edilmis ya da edilmemis bir piridin bilesigi olabilir.
Reaksiyon bir solventin yoklugunda ya da reaksiyonu etkilemeyen bir solvent
kullanarak gerçeklestirilebilir. Bir solventin kullanildigi durumlarda, amidler (örnegin
dimetilformamid, dimetilasetamid), nitriller (örnegin asetonitril), sülfoksitler (örnegin
dimetilsülfoksit), eterler (örnegin dietil eter, tetrahidrofuran), esterler (örnegin etil
asetat, bütil asetat), aromatik hidrokarbonlar (örnegin benzen, ksilen, tolüen),
alkoller (örnegin metanoli etanol, propanol), ketonlar (örnegin aseton, metil etil
keton), alifatik hidrokarbonlar (örnegin heksan, heptan, oktan), ya da halojenlenmis
hidrokarbonlar (örnegin diklorometan, kloroform, klorobenzen, diklorobenzen) gibi
solventler ya da su tek basina ya da iki veya daha fazlasinin kombinasyonlari olarak
kullanilabilir. Dimetilformamid, asetonitril, eterler, diklorometan ya da kloroform
kullanilmasi tercih edilmektedir.
Reaksiyon, genel olarak -80 ila 100°C arasinda gerçeklestirilebilir, bununla birlikte
reaksiyonun 20 ila 50°C araliginda gerçeklestirilmesi tercih edilmektedir.
Yukaridaki formül (Ie)'ye sahip olan bilesikler, yukaridaki formül (IXb)'ye sahip olan
bir bilesigin, bir bazin varliginda ya da yoklugunda bir dehidrasyon-kondansasyon
ajani kullanarak R4e-COOH formülüne (burada R4e degiskeni yukarida tanimlandigi
gibidir) sahip olan bir karboksilik asitle reaksiyona sokulmasi yoluyla elde edilebilir.
Disikloheksilkarbodiimid ya da 1-etiI-3-(3-dimetilaminopropil)karbodiimid
hidroklorür gibi bir karbodiimid bilesigi, dehidrasyon-kondansasyon ajani olarak
kullanilabilir.
Reaksiyon bir bazin varliginda gerçeklestirildigi zaman, söz konusu baz örnegin
potasyum karbonat ya da sodyum karbonat gibi bir karbonat, trietilamin gibi bir
tersiyer amin ya da piridin veya 4-dimetilaminopiridin gibi sübstitüe edilmis ya da
edilmemis bir piridin bilesigi olabilir.
Söz konusu reaksiyon tercih edilen sekliyle bir solvent kullanarak gerçeklestirilir.
Örnegin amidler (örnegin dimetilformamid, dimetilasetamid), nitriller (örnegin
asetonitril), sülfoksitler (örnegin dimetilsülfoksit), eterler (örnegin dietil eter,
tetrahidrofuran), esterler (örnegin etil asetat, bütil asetat), aromatik hidrokarbonlar
(örnegin benzen, ksilen, tolüen), ketonlar (örnegin aseton, metil etil keton), alifatik
hidrokarbonlar (örnegin heksan, heptan, oktan), ya da halojenlenmis hidrokarbonlar
(örnegin diklorometan, kloroform, klorobenzen, diklorobenzen) tek basina ya da iki
veya daha fazlasinin kombinasyonlari olarak kullanilabilir. Diklorometan ya da
kloroform kullanilmasi tercih edilmektedir.
Reaksiyon, genel olarak -80 ila 100°C arasinda gerçeklestirilebilir, bununla birlikte
reaksiyonun 20 ila 50°C araliginda gerçeklestirilmesi tercih edilmektedir.
Yukaridaki formül (le)'ye sahip olan bilesikler, yukaridaki formül (IXa)'ya sahip
olan bir bilesigin, bir bazin varliginda ya da yoklugunda ArCH(R1)X formülüne
(burada Ar, R1 ve X degiskenleri yukarida tanimlandigi gibidir) sahip olan bir
bilesikle reaksiyon sokulmasi yoluyla elde edilebilir.
Reaksiyon bir bazin varliginda gerçeklestirildigi zaman, söz konusu baz örnegin
sodyum hidrit gibi bir alkali metal hidrit, potasyum karbonat ya da sodyum karbonat
gibi bir karbonat, potasyum hidroksit ya da sodyum hidroksit gibi bir alkali metal
hidroksit, trietilamin gibi bir tersiyer amin ya da piridin veya 4-dimetilaminopiridin
gibi sübstitüe edilmis ya da edilmemis bir piridin bilesigi olabilir.
Reaksiyon bir solventin yoklugunda ya da reaksiyonu etkilemeyen bir solvent
kullanarak gerçeklestirilebilir. Bir solventin kullanildigi durumlarda, amidler (örnegin
dimetilformamid, dimetilasetamid), nitriller (örnegin asetonitril), sülfoksitler (örnegin
dimetilsülfoksit), eterler (örnegin dietil eter, tetrahidrofuran), esterler (örnegin etil
asetat, bütil asetat), aromatik hidrokarbonlar (örnegin benzen, ksilen, tolüen),
alkoller (örnegin metanol, etanol, propanol), ketonlar (örnegin aseton, metil etil
keton), alifatik hidrokarbonlar (örnegin heksan, heptan, oktan), ya da halojenlenmis
hidrokarbonlar (örnegin diklorometan, kloroform, klorobenzen, diklorobenzen) gibi
solventler ya da su tek basina ya da iki veya daha fazlasinin kombinasyonlari olarak
kullanilabilir. Dimetilformamid, asetonitril, eterler, diklorometan ya da kloroform
kullanilmasi tercih edilmektedir.
Reaksiyon, genel olarak -80 ila 100°C arasinda gerçeklestirilebilir, bununla birlikte
reaksiyonun 20 ila 50°C araliginda gerçeklestirilmesi tercih edilmektedir.
(le)'nin kimyasal formül (lXa)'ya sahip olan bir bilesikten (IX) vasitasiyla
sentezlendigi durumlarda ya da (Ie)'nin kimyasal formül (IXa)'ya sahip olan bir
bilesikten (IXb) vasitasiyla sentezlendigi durumlarda, reaksiyonlar (IX) ya da (IXb)
uzaklastirilmadan sirali olarak gerçeklestirilebilir ya da (IXa) ila (le) reaksiyonlari,
ayni reaksiyon kabi içerisinde es zamanli olarak ilerleyebilir.
(Örnekler)
Simdi, bulus, bulus çalisma örnekleri ile kisitli olmamasina karsin, çalisma örnekleri
vasitasiyla asagida daha detayli açiklanmaktadir.
içerisinde çözündürüldü, 41 mL (30 g, 300 mmol) trietilamin eklendi ve bu karisim
trifloroasetik anhidrit eklendi ve bu karisim oda sicakliginda 2 saat boyunca
karistirildi. Reaksiyon tamamlandiktan sonra, reaksiyon karisimi yaklasik 100 mL
buzlu su içerisine aktarildi ve 10 dakika boyunca karistirildi. Bu karisim daha sonra
bir ayirma hunisine transfer edildi ve sivi-sivi ekstraksiyonu gerçeklestirildi. (2)
Organik faz iki kez 150 mL su ile yikandi, iki kez 150 mL % 1 sulu HCI solüsyonu
ile yikandi, daha sonra susuz magnezyum sülfat üzerinde kurutuldu ve düsük
basinç altinda kurutuldu, 36 g 2,2,2-trifl0ro-N-(piridin-2(1H)-iliden)asetamid (verim
149.5, 155.3 (q)
içerisinde çözündürüldü, daha sonra yukaridaki yöntem vasitasiyla elde edilen 24
potasyum karbonat eklendi ve 6 saat boyunca isitma altinda geri akis islemi, bunu
takiben oda sicakliginda 10 saat karistirma gerçeklestirildi. Reaksiyonun
tamamlanmasindan sonra, reaksiyon karisimi filtrelendi ve filtrat düsük basinç
altinda konsantre edildi. (3) Kristalizasyon gerçeklestirmek için konsantreye dietil
eter eklendi ve sonuçta olusan kristaller filtrasyon yoluyla toplandi, daha sonra dietil
eter ve su ile iyice yikandi. (3) Bu sekilde elde edilen kristaller 60°C*de ve 1 saat
boyunca düsük basinç altinda kurutuldu ve 26 gram hedef bilesigi (verim % 66)
(3) Kristallerin Toz X-lsini Kirinim Analizi
Toz x-isini kirinim analizinde, ölçüm, asagidaki kosullar altinda gerçeklestirildi.
Aparat: RINT-
X-isinlari: Cu-Kci (40 W, 20 mA)
Tarama araligi: 4 ila 40°
Örnekleme genisligi: 0.02°
Tarama hizi: 1°/dak
(4) Diferansiyel Taramali Kalorimetri (DSC)
Diferansiyel taramali kalorimetride, ölçüm, asagidaki kosullar altinda
gerçeklestirildi.
Aparat: DSG-60 Örnek hücre: alüminyum
Sicaklik araligi: 50 ila 250°C (sicaklik artis hizi, 10°C/dak)
Sonuçlar Sekil 2'de gösterilmektedir.
(5) Ek olarak, rekristalizasyonu gerçeklestirmek için asagida (i) ila (iv)
adimlarinda (ikinci ila besinci hazirlama yöntemleri) tarif edilen yöntemler
kullanarak benzer kristaller elde edildi. Sonuçta olusan kristaller, yukarida
gösterilenle ayni ölçüm kosullari altinda toz x-isini kirinim analizine ve diferansiyel
taramali kalorimetriye tabi tutuldu.
(i) Ikinci Hazirlama Yöntemi
ve bu karisim bir sicak su banyosu üzerinde 65°Ciye isitildi ve tam çözünme
gerçeklesti. Solüsyon, yavas bir biçimde oda sicakliginda geldi ve gece boyunca
beklemeye birakildi. Çökelen kristallerfiltrasyon yoluyla toplandi ve 95:5 heksan ve
etil asetat solüsyonundan az miktarla yikandi. Yikanan kristaller bir kurutma
cihazina yerlestirildi ve 2 saat boyunca düsük basinç altinda kurutuldu ve 349 mg
beyaz kristaller verdi.
Toz x-isini kirinim analizinin sonuçlari asagidaki gibi oldu (SEKIL 3). Kirinim açisi
Diferansiyel tarama analizinin sonuçlari SEKIL 4'te gösterilmektedir.
(ii) Üçüncü Hazirlama Yöntemi
28 mL 2-propanol Bilesik 212iye (1.0 9) eklendi ve bu karisim bir sicak su banyosu
Üzerinde 65°C'ye isitildi ve tam çözünme gerçeklesti. Solüsyon, yavas bir biçimde
oda sicakliginda geldi ve gece boyunca beklemeye birakildi. Çökelen kristaller
filtrasyon yoluyla toplandi ve az miktarda 2-pr0pna0l ile yikandi. Yikanan kristaller
daha sonra bir kurutma cihazina yerlestirildi ve 2 saat boyunca düsük basinç altinda
kurutuldu ve 695 mg beyaz kristaller verdi.
Diferansiyel tarama analizinin sonuçlari SEKIL 5'te gösterilmektedir.
(iii) Dördüncü Hazirlama Yöntemi
Yaklasik 30 mL tolüen Bilesik 212'ye (700 mg) eklendi ve bu karisim bir sicak su
banyosu üzerinde 65°Clye isitildi ve tam çözünme gerçeklesti. Solüsyon, yavas bir
biçimde oda sicakliginda geldi ve gece boyunca beklemeye birakildi. Çökelen
kristaller filtrasyon yoluyla toplandi ve az miktarda tolüen ile yikandi. Yikanan
kristaller daha sonra bir kurutma cihazina yerlestirildi ve 2 saat boyunca düsük
basinç altinda kurutuldu ve 440 mg beyaz kristaller verdi.
Toz x-isini kirinim analizinin sonuçlari asagidaki gibi oldu (SEKIL 6). 6). Kirinim
Diferansiyel tarama analizinin sonuçlari SEKIL 7'de gösterilmektedir.
Yaklasik 2 mL metanol ve yaklasik 2 mL su Bilesik 212'ye (50 mg) eklendi ve bu
karisim bir sicak su banyosu üzerinde 65°C'ye isitildi ve tam çözünme gerçeklesti.
Solüsyon oda sicakliginda geldi ve gece boyunca beklemeye birakildi. Çökelen
kristaller filtrasyon yoluyla toplandi ve 16 mg beyaz kristaller verdi.
Diferansiyel tarama analizinin sonuçlari SEKIL 8'de gösterilmektedir.
Sentez Örnegi 14, Adim (1) için Alternatif Yöntem
çözündürüldü, bunu takiben trietilamin eklendi, daha sonra buzlu
sogutma altinda trifloroasetik anhidrit eklendi. Karistirma islemi
sonrasinda 2 saat boyunca oda sicakliginda devam etti, daha sonra 10 mL etil
asetat ve 10 mL su eklendi, bundan sonra karisim tekrar karistirildi ve sivi-sivi
ekstraksiyonu gerçeklestirildi. Etil asetat fazi iki kez 10 mL su ile yikandi, daha
sonra susuz magnezyum sülfat üzerinde kurutuldu ve düsük basinç altinda
konsantre edildi ve 1.56 9 2,2,2-trifloro-N-(piridin-2(1H)-iliden)asetamid (verim %
77.2) verdi.
Sentez Örnegi 14, Adim (1) için Alternatif Yöntem 2
mL tetrahidrofuran (THF) içerisinde 0.94 9 (10 mmol) miktarinda 2-aminopiridin
dimetilaminopiridin eklendi ve 22 saat boyunca geri akis islemi gerçeklestirildi. THF
distilasyon yoluyla uzaklastirildi, bunu takiben bir silika jel kolon ile saflastirma
gerçeklestirildi (gelisen solvent: 4:1 heksan ve etil asetat solüsyonu) ve 0.26 9
2,2,2-trifloro-N-(piridin-2 (1 H)-iliden)asetamid (verim % 13,7) verdi.
Sentez Örnegi 14, Alternatif Yöntem
dimetilformamit (DMF) içerisinde çözündürüldü, 1.75 9 (18.6 mmol) 2-aminopiridin
eklendi ve karisim 8 saat boyunca 80°C'de ve 5 saat boyunca oda sicakliginda
karistirildi. Reaksiyonun tamamlanmasindan sonra, DMF düsük basinç altinda
damitildi ve asetonitril eklendi, bundan sonra bir kati ayristirildi. Kati, filtrasyon
yoluyla toplandi, asetonitril ile iyice yikandi, daha sonra kurutuldu ve 2.07 9 1-[(6-
kloropiridin-3-Il)metil]piridin-2(1 H)-imine hidroklorür (verim °/o 44) verdi.
il)metil]piridin-2(1H)-imine hidroklorür 5 mL susuz diklorometan içerisinde
çözündürüldü, buzlu sogutma altinda sirasiyla 122 mg (1.00 mmol) DMAP ve 50
mg (0.24 mmol) trifloroasetik anhidrit eklendi ve bu karisim oda sicakliginda 1 saat
boyunca karistirildi. Reaksiyon tamamlandiktan sonra, reaksiyon karisimi
diklorometan ile seyreltildi, % 1 hidroklorik asitle yikandi, daha sonra susuz
magnezyum sülfat üzerinde kurutuldu. Düsük basinç altinda distilasyon yoluyla
diklorometan uzaklastirildi ve 42 mg'lik bir miktarda hedef bilesigi (verim % 67)
verdi. NMR spektrumu, yukarida tarif edilen yöntemle elde edilen ürününki ile
Bilesik 1)
mL susuz kloroform içerisinde siyanojen bromür (220 mg, 2.09 mmol)
çözündürüldü ve solüsyon O°C'ye sogutuldu. Buna damlatarak 10 mL susuz
kloroform içerisinde çözündürülmüs 500 mg (3.49 mmol) 2-kloro-5-
aminometilpiridin solüsyonu eklendi ve sonuçta olusan karisim 1 saat boyunca
0°C'de karistirildi. Reaksiyon karisimi filtrelendi, daha sonra su eklendi ve sivi-sivi
ekstraksiyonu gerçeklestirildi, bunu takiben kloroform fazi susuz magnezyum sülfat
üzerinde kurutuldu ve düsük basinç altinda konsantre edildi. Konsantre, silika jel
kolon kromatografisi (heksan/etil asetat = 121) ile saflastirildi ve 122 mg (verim %
Karsilastirma Örnegi 2: N-l1-((6-kloropiridin-3-il)metil)piridin-2(1H)-
ilidenlsivanamid (Patent Dokümani 6, Bilesik 20)
Sentez Örnegi 14'te tarif edilen alternatif yöntemle elde edilen 128 mg (0.58 mmol)
1-[(6-kloropiridin-3-iI)metil]piridine-2(1H)-imine 5 mL susuz dimetilformamit
içerisinde çözündürüldü, 40 mg NaH (yag içerisinde % 60 dispersiyon olarak)
eklendi (net agirlik, 24 mg; 1.04 mmol) ve bu karisim 30 dakika boyunca oda
sicakliginda karistirildi. Sonra, 60 mg (0.57 mmol) siyanojen bromür eklendi ve
sonuçta olusan karisim gece boyunca karistirildi. Reaksiyonun tamamlanmasini
takiben reaksiyon karisimina su ve etil asetat eklendi ve sivi-sivi ekstraksiyonu
gerçeklestirildi. Organik faz, susuz magnezyum sülfat üzerinde kurutuldu, daha
sonra düsük basinç altinda konsantre edildi. Konsantre, bir TLC plaka üzerinde
saflastirildi (% 100 etil asetat ile gelistirilen bir 0.5 mm plaka) ve 14 mg hedef bilesigi
verdi (verim % 10).
7.75 (1 H, dd), 8.40 (1 H, d)
Karsilastirma Örnegi 3: N-l1-((6-kloropiridin-3-il)metil)piridin-2(2H)-ilidenlasetamid
Sentez Örnegi 14'te tarif edilen alternatif yöntemle elde edilen 118 mg (0.46 mmol)
1-[(6-kl0ropiridin-3-il)metil] piridine-2(1H)-imine hidroklorüre susuz diklorometan
(20 mL) eklendi, bunu takiben trietilamin ve 33 mL
asetil klorür eklendi ve bu karisim 15 dakika boyunca oda sicakliginda karistirildi.
Reaksiyon, reaksiyon karisimina su eklenerek durduruldu ve kloroform ve su ile
sivi-sivi ekstraksiyonu gerçeklestirildi. Organik faz, doygun sulu amonyum klorür
solüsyonu ile yikandi, daha sonra konsantre edildi. Buna heksan eklenerek bir kati
çökeltildi. Kati, filtrasyon yoluyla toplandi, daha sonra iyice kurutuldu ve 21 mg
hedef bilesigi verdi (verim % 17).
1H-NiviR (CDCls, ö, ppm): , 7.48
triroropropan-Z-on (Patent Dokümani 5, Örnek 4)
CIA N `coca,
dimetilformamit (15 mL) eklendi ve bu karisim 0°C'ye sogutuldu. Buna damlatarak
1,1,1-trifloro-acet0ne eklendi ve karistirma islemi 10
dakika boyunca 0°C'de gerçeklestirildi. Buna karbon
disülfit eklendi ve karistirma islemi 1 saat boyunca 50°Clde gerçeklestirildi. Sonra,
reaksiyon karisimi 0°C`ye sogutuldu, metil iyodür
eklendi ve bu karisim gece boyunca oda sicakliginda karistirildi. Reaksiyon
tamamlandiktan sonra, reaksiyon karisimi buzlu su içerisine aktarildi ve buz
tamamen eriyene kadar karistirma gerçeklestirildi. Reaksiyon karisimi bir ayrima
hunisine transfer edildi ve etil asetatla ekstrakte edildi. Organik katman doygun
tuzlu su ile yikandi, daha sonra susuz magnezyum sülfat üzerinde kurutuldu ve
düsük basinç altinda konsantre edildi. Konsantre, silika jel kromatografisi
(heksan/etil asetat = 95:5) ile saflastirildi ve hedef bilesigi içeren fraksiyonlar
toplandi ve düsük basinç altinda konsantre edildi. Buna heksan eklendi, bundan
sonra bir kati çökeldi. Kati, filtrasyon yoluyla toplandi ve heksanla yikandi, daha
ve bu karisim gece boyunca karistirildi. Reaksiyon tamamlandiktan sonra,
reaksiyon karisimi düsük basinç altinda konsantre edildi, bundan sonra asetonitril
eklendi ve çözünmeyen madde filtrasyon yoluyla uzaklastirildi. Filtrat düsük basinç
1,2-diamine verdi.
8 mL susuz asetonitril içerisinde yukaridaki yöntemle elde edilen 77 mg (0.42 mmol)
N-((6-kloropiridin-3-il)metil)etan-1,2-diamine solüsyonu, yukaridaki yöntemle elde
ve bu karisim 40 dakika boyunca isitma altinda geri akis tabi tutuldu. Reaksiyonun
tamamlanmasini takiben reaksiyon karisimi oda sicakligina getirildi ve düsük
basinç altinda konsantre edildi, bundan sonra su ve etil asetat eklendi ve sivi-sivi
ekstraksiyonu gerçeklestirildi. Organik faz susuz magnezyum sülfat ile yikandi,
daha sonra düsük basinç altinda konsantre edildi ve konsantre, 59 mg hedef
bilesigi (verim % 69) verecek sekilde silika jel kolon kromatografisi (heksan/etil
trifloropropan-Z-on (Patent Dokümani 5. Örnek 3)
mL etanol içerisinde çözündürülen 36 mg (0.46 mmol) 2-aminoetantiy0l
solüsyonu, Karsilastirma Örnegi 4`te tarif edilen yöntemle elde edilen 100 mg (0.46
boyunca isitma altinda geri akisa tabi tutuldu, daha sonra 13 saat boyunca oda
sicakliginda karistirildi. Reaksiyon tamamlandiktan sonra, düsük basinç altinda
etanol damitildi, bundan sonra kondensat etil asetat içerisinde çözündürüldü ve
suyla bir kez yikandi. Yikanan ürün susuz magnezyum sülfat üzerinde kurutuldu,
daha sonra düsük basinç altinda konsantre edildi ve 73 mg (verim % 81) 1,1,1-
trifloro-3-(thiazolidin-2-iliden)propan-: 3.35
8 mL susuz asetonitril içerisinde çözündürülen 2-klor0-5-kl0rometilpiridine (80 mg,
(thiaolidin-2-iliden)propane-2-0nea eklendi ve bu karisim 2 saat boyunca isitma
altinda geri akisa tabi tutuldu. Reaksiyon tamamlandiktan sonra, reaksiyon karisimi
oda sicakliginda getirildi, çözünmeyen madde filtrasyon yoluyla uzaklastirildi ve
filtrat düsük basinç altinda konsantre edildi. Konsantre, silika jel kolon
kromatografisi (heksan/etil asetat = 1:1 -› 13) ile saflastirildi ve 53 mg (verim %
50) hedef bilesigi verdi.
Karsilastirma Örnegi 6: 3-[1-((6-kl0ropiridin-3-il)metil)imidazolidin-2-ilidenl-
Karsilastirma Örnegi 4'te tarif edilen yöntemle elde edilen 31 mg (0.10 mmol) 3-[1-
susuz diklorometan içerisinde çözündürüldü, daha sonra sirasiyla 20 mL (0.25
mmol, 20 mg) piridine ve 28 mL (0.20 mmol, 42 mg) trifloroasetik anhidrit eklendi
ve bu karisim 30 dakika boyunca oda sicakliginda karistirildi. Reaksiyonun
ilerlemesi ince tabaka kromatografisi ile denetlendi, bundan sonra sistemde kalan
bir miktar baslangiç materyali oldugu saptandi. Sonuç olarak, 84 mL (0.60 mmol,
62 mg) daha trifloroasetik anhidrit eklendi ve oda sicakliginda 1 saat boyunca
karistirma gerçeklestirildi. Reaksiyon tamamlandiktan sonra, reaksiyon karisimi
düsük basinç altinda konsantre edildi, daha sonra bir PLC plakasi (heksan/etil =
28 ile gelistirilen bir 0.5 mm plaka) üzerinde saflastirildi ve 30 mg hedef bilesigi
(verim % 75) verdi.
8.35 (1H, d)
Karsilastirma Örnegi 7: N-[1-((6-kl0ropiridin-3-il)metil)imidazolidin-2-ilidenl-2,2,2-
trifloroasetamid (Patent Dokümani 5. Örnek 7)
mL piridin içerisinde dimetilkarbonimidoditiyoat metansülfonik asit klorür (4.25 9,
18.2 mmol) çözündürüldü, damlatarak trifloroasetik
anhidrit eklendi ve bu karisim oda sicakliginda gece boyunca karistirildi. Reaksiyon
karisimi düsük basinç altinda konsantre edildi ve diklorometan ve su kullanarak
sivi-sivi ekstraksiyonuna tabi tutuldu. Sonuçta olusan organik faz susuz
magnezyum sülfat üzerinde kurutuldu, daha sonra konsantre edildi ve 5.36 9
dimetil(2,2,2-trifloroacetyl)karbonimid0ditiyoat (verim % 100) verdi.
Örnegi 4'te tarif edilen yöntemle sentezlendi. Bu, 40 mL susuz asetonitril içerisinde
çözündürüldü, yukaridaki yöntemle elde edilen 4.60 9 (21.3 mmol) of the
dimetil(2,2,2-trikloroacetyl)karbonimidoditiyoat eklendi ve sonuçta olusan karisim
90 dakika boyunca isitma altinda geri akisa tabi tutuldu. Reaksiyon tamamlandiktan
sonra, reaksiyon karisimi oda sicakligina getirildi, bundan sonra solvent düsük
basinç altinda damitildi. Çökelen kati filtrasyon yoluyla toplandi ve az miktarda
asetonitril ile yikandi, 2.17 9 hedef bilesigi (verim % 33) verdi.
Karsilastirma Örnegi 8: N-[3-((6-kloropiridin-3-il)metil)thiazolidin-2-ilIden]-2,2,2-
trifloroasetamid (Patent Dokümani 5. Örnek 6)
77 mg (1.0 mmol) 2-aminoetantiyola etanol (20 mL) eklendi, Karsilastirma Örnegi
7'de'tarif edilen yöntemle sentezlenen 216 mmol (1.0 mmol) dimetil (2,2,2-
trifloroacetyl)karbonimidoditiyoat eklendi ve bu karisim oda sicakliginda gece
boyunca karistirildi. Reaksiyon tamamlandiktan sonra, solvent düsük basinç
altinda damitildi ve saflastirma islemi silika jel kolon kromatografisi (heksan/etil
iliden)asetamid (verim % 51) verdi. Bu reaksiyon ayni sentez yöntemiyle bir kez
daha gerçeklestirildi ve kombine miktarda 350 mg 2,2,2-triflor0-N-(thiazolidin-2-
iliden) asetamid verdi.
(thiazolidin-2-iliden)asetamid dimetilformamit (2 mL) ve tetrahidrofuran (18 mL)
potasyum karbonat eklendi ve bu karisim 20 saat boyunca isitma altinda geri akisa
tabi tutuldu. Reaksiyon tamamlandiktan sonra, reaksiyon karisimi oda sicakligina
getirildi, çözünmeyen madde filtrasyon yoluyla uzaklastirildi ve filtrat düsük basinç
altinda konsantre edildi. Konsantre, bir TLC plaka üzerinde saflastirildi (% 100 etil
asetat ile gelistirilen iki 0.5 mm plaka) ve 230 mg hedef bilesigi verdi (verim % 87).
7.72 (1H, dd), 8.36 (1H, d)
Erime noktasi: 96°C
ÖRNEK FORMÜLASYONLAR
Formülasvon Örnegi 2: Granüller
Bilesik 212 Agirlikça % 2
Sanx P-252 Agirlikça % 1
Baglayici Agirlikça % 1.5
Granülasyon arttirici Agirlikça % 0.5
Kil Agirlikça % 91
Yukaridaki bilesenler tek biçimli olarak ögütüldü ve karistirildi, bunu takiben su
eklendi ve karisim iyice yogruldu. Yogrulan materyal granüle edildi ve kurutuldu ve
granüller verdi.
Yukaridaki bilesenler tek biçimli olarak karistirildi ve ögütüldü ve sulandirilabilir bir
toz verdi.
Formülasvon Örnegi 4: Suda Dagitilabilir Granüller
Bilesik 212 Agirlikça % 30
Kil Agirlikça % 60
Dekstrin Agirlikça % 5
AIkiI-maleik asit kopolimeri Agirlikça % 4
Sodyum laurii sülfat Agirlikça % 1
Yukaridaki bilesenler tek biçimli olarak ögütüldü ve karistirildi, bunu takiben su
eklendi ve karisim iyice yogruldu. Yogrulan materyal granüle edildi ve kurutuldu ve
suda disperslenebilir granüller verdi.
Formülasvon Örnegi 11: Damla icin sivi formülasvon
Bilesik 212 Agirlikça % 48
Etanol Agirlikça % 52
Yukaridaki bilesenler tek biçimli olarak karistirildi ve sivilastirilmis bir damla
formülasyonu verdi.
Ek olarak, hem mevcut bulusun bir bilesigini hem de aska bir zararli kontrol ajanini
içeren karma bir formülasyon örnegi asagida saglanmaktadir.
Formülasvon Örnegi 12: Granüller
Bilesik 212 Agirlikça % 2
Propenazol Agirlikça % 24
Baglayici Agirlikça % 3.0
Granülasyon arttirici Agirlikça % 0.5
Kil Agirlikça % 70.5
Yukaridaki bilesenler tek biçimli olarak ögütüldü ve karistirildi, bunu takiben su
eklendi ve karisim iyice yogruldu. Yogrulan materyal granüle edildi ve kurutuldu ve
granüller verdi.
TEST ÖRNEKLERI
Yapraga Uygulama Testleri
Test Örnegi 12: Kahverenqi Kanatli Yesil Yarimkanatli Kontrol Testi
Tarlada toplanmis olan genç elmalara, % 50 aseton/su (agirlikça % 0.05 Tween 20
içeren) olacak sekilde hazirlanan önceden belirlenmis bir konsantrasyonda bulus
bilesiklerinin solüsyonlari püskürtüldü. Isleme tabi tutulan meyveler havayla
kurutuldu, plastik kapiara yerlestirildi ve her kap içerisine iki yetiskin kahverengi
kanatli yesil yarimkanatli birakildi. Böceklerin birakilmasini takiben, meyveler ve
böcekler 25°C'de bir inkübasyon haznesinde tutuldu (16 saat isik, 8 saat karanlik
periyodu). Birakildiktan alti gün sonra, canli ve ölü böceklerin sayimi yapildi ve
mortalite asagidaki formülden hesaplandi.
Mortalite (%) = [ölü böceklerin sayisi/[canli böceklerin sayisi + ölü böceklerin
Bu sonuçlardan, 500 ppm yapraga uygulamayla, Bilesik 212 en az % 80 mortaliteye
sahip olan yüksek bir insektisidal aktivite sergiledi.
Test Örnegi 13: Pirinç Yaprak Biti Kontrol Testi
Aseton içerisinde önceden belirlenen bir konsantrasyonda hazirlanan bulus
bilesikler, tarladan toplanan yetiskin bitlerin sirtlarina bir mikrosiringa kullanarak 1
mL'Iik (böcek basina) bir miktarda lokal olarak uygulandi. Kimyasal tedaviyi takiben,
her bitki üzerine bes bit olacak sekilde bitler pirin fidelerine transfer edildi ve fideler
ve bitler 25°C'de bir inkübasyon haznesinde tutuldu (16 saat isik, 8 saat karanlik
periyodu). Tedaviden kirk sekiz saat sonra, canli ve ölü böceklerin sayimi yapildi
ve mortalite asagidaki formülden hesaplandi.
Mortalite (%) = [ölü böceklerin sayisi/[canli böceklerin sayisi + ölü böceklerin
Bu sonuçlardan, 0.5 mg/böcek dozajinda, Bilesik 1, 8 ve 212, en az % 80
mortaliteye sahip olan yüksek insektisidal aktiviteler sergiledi.
Test Örnegi 18: Pirinç Su Ekin Biti Kontrol Testi
Kaplarda yetistirilen pirinç fideleri, % 10 aseton/su olacak sekilde hazirlanan
önceden belirlenmis bir konsantrasyonda bulus bilesiklerinin solüsyonlari ile toprak
sulama islemine tabi tutuldu. Tedaviden iki gün sonra, her fide üzerine bes yetiskin
pirinç su ekin biti birakildi. Fideler ve böcekler daha sonra 25°C'de bir inkübasyon
haznesinde tutuldu (16 saat isik, 8 saat karanlik periyodu). Birakildiktan üç gün
sonra, canli ve ölü böceklerin sayimi yapildi ve mortalite asagidaki formülden
hesaplandi. Test iki tekrar olarak gerçeklestirildi.
Mortalite (%) = [ölü böceklerin sayisi/[canli böceklerin sayisi + ölü böceklerin
Bu sonuçlardan, 0.1 mg/fide dozajinda, Bilesik 212 en az % 80 mortaliteye sahip
olan yüksek bir insektisidal aktivite sergiledi.
Endüstriyel Ölçekte Uygulanabilirligi
Mevcut bulusun amin türevleri, lahana yaprak güvesi, genel tarla kurtlari, pamuk
biti, küçük kahverengi yaprak pireleri, kahverengi pirinç pireleri, yesil pirin yaprak
pireleri, sert gövdeli kene Haemaphysa/is Iongicorni's, ve baska birçok zararliya
karsi kusursuz insektisidal etkilere sahiptir. Ayrica, düsük insektisit duyarliligina
sahip olan özellikle yaprak pireleri gibi böceklere karsi da güçlü etkiler sergileyebilir.
Bunun yani sira, bunlar ayni zamanda toprak ve bitki kültivasyon ortamlarinda
etkilidir ve isçinin kimyasallara maruz kalma risklerini azaltabildiklerinden zararlilari
kontrol etmek için güvenle kullanilabilir. Bu nedenle, mevcut bulus, zararli kontrolü
alaninda son derece faydali olabilir.
TANIMLAMADA BELIRTILEN REFERANSLAR
Basvuran tarafindan belirtilen bu referanslar listesi yalnizca okuyucu için bir kolaylik
saglamasi içindir. Avrupa patent dokümaninin bir parçasini teskil etmez.
Referanslarin derlenmesinde büyük bir özen gösterilmis olmakla birlikte hatalar
veya eksiklikler olabilir ve EPO bu anlamda hiçbir sorumluluk üstlenmemektedir.
Tarifnamede Atifta Bulunulan Patent Belgeleri
JP 259738 A
Patent Literatüründe Yer Almayan Açiklamalar
Journal of Photochemistry and Photobiology B: BioI-ogy, 201 O, vol. 98 (1
2009 '
- *5330
1 5533313
Claims (3)
1. Bir hayvan disi denekte, bir zararli kontrol ajaninin kullanilmasi adimini içeren bir yöntem olup, özelligi; burada söz konusu zararli kontrol ajaninin N-[1-((6- kloropiridin-S-il)metil)piridin-2(1H)-iliden]-2,2,2-trifloroasetamidden seçilen en az bir amin türevini veya bunun bir tuzunu içermesi, ve söz konusu zararlinin kahverengi kanatli yesil yarimkanatli, pirinç su ekin biti, adzuki fasulyesi ekin biti, çizgili pire böcegi ve pirinç yaprak bitinden olusan gruptan seçilen en az bir zararli türü olmasidir.
2. Istem 1'e göre yöntem olup, özelligi; bitki tohumlari, kökleri, yumrulari, soganlari, rizomlari, topragi, nutrikültür içerisindeki bir besleyici solüsyonu, nutrikültür içerisindeki bir kati kültür ortami ya da bitkileri gelistirmek için bir tasiyicinin, böcek kontrol ajani ile isleme tabi tutulmasi, bu suretle de amin türevinin bitkiler içerisine penetre edilmesi ve yerlestirilmesi adimini içermesidir.
3. Insan veya hayvan vücudunun tedavisi hariç olmak üzere zararlilari kontrol etmede N-[1-((6-klor0piridin-3-il)metil)piridin-2(1H)-iliden]-2,2,2-trifloroasetamid ve bunun bir tuzundan seçilen bir amin türevinin kullanimi olup, özelligi; burada söz konusu zararlinin kahverengi kanatli yesil yarimkanatli, pirinç su ekin biti, adzuki fasulyesi ekin biti, çizgili pire böcegi ve pirinç yaprak bitinden olusan gruptan seçilen en az bir zararli türü olmasidir.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2010194584 | 2010-08-31 |
Publications (1)
Publication Number | Publication Date |
---|---|
TR201816134T4 true TR201816134T4 (tr) | 2018-11-21 |
Family
ID=45772762
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
TR2018/16134T TR201816134T4 (tr) | 2010-08-31 | 2011-08-26 | Zararli kontrol ajani |
Country Status (34)
Country | Link |
---|---|
US (5) | US8957214B2 (tr) |
EP (5) | EP2984930B1 (tr) |
JP (2) | JPWO2012029672A1 (tr) |
KR (2) | KR20130132775A (tr) |
CN (3) | CN103254125B (tr) |
AP (1) | AP3539A (tr) |
AU (1) | AU2011297160B2 (tr) |
BR (1) | BR112013004818B8 (tr) |
CA (1) | CA2808144C (tr) |
CL (2) | CL2013000570A1 (tr) |
CO (1) | CO6680699A2 (tr) |
CR (2) | CR20200540A (tr) |
CU (1) | CU24170B1 (tr) |
DO (1) | DOP2013000046A (tr) |
EA (1) | EA022848B1 (tr) |
EC (1) | ECSP13012527A (tr) |
ES (2) | ES2693089T3 (tr) |
GE (1) | GEP201706728B (tr) |
HK (1) | HK1188595A1 (tr) |
HU (2) | HUE026428T2 (tr) |
IL (2) | IL224592A (tr) |
MA (1) | MA34551B1 (tr) |
MX (1) | MX363956B (tr) |
MY (1) | MY163072A (tr) |
NI (1) | NI201300025A (tr) |
NZ (4) | NZ722021A (tr) |
PE (1) | PE20131380A1 (tr) |
PL (2) | PL2631235T3 (tr) |
SG (1) | SG187883A1 (tr) |
TR (1) | TR201816134T4 (tr) |
TW (2) | TWI554210B (tr) |
UA (1) | UA109149C2 (tr) |
WO (1) | WO2012029672A1 (tr) |
ZA (1) | ZA201301156B (tr) |
Families Citing this family (331)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20130132775A (ko) * | 2010-08-31 | 2013-12-05 | 메이지 세이카 파루마 가부시키가이샤 | 유해 생물 방제제 |
CN103781764B (zh) * | 2011-08-26 | 2016-07-20 | 明治制果药业株式会社 | 有害生物防除剂的制造法 |
TWI601716B (zh) * | 2012-02-29 | 2017-10-11 | Meiji Seika Pharma Co Ltd | Nitrogen-containing heterocyclic derivatives having 2-imino group and pest control agent containing the same |
CN112244015B (zh) * | 2012-02-29 | 2022-05-17 | 株式会社Mmag | 包括新型亚氨基吡啶衍生物的有害物防治组合物 |
JP2015512905A (ja) | 2012-03-29 | 2015-04-30 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 有害動物を駆除するためのn−置換複素二環式化合物および誘導体ii |
WO2013144213A1 (en) | 2012-03-30 | 2013-10-03 | Basf Se | N-substituted pyridinylidene compounds and derivatives for combating animal pests |
WO2013144223A1 (en) | 2012-03-30 | 2013-10-03 | Basf Se | N-substituted pyrimidinylidene compounds and derivatives for combating animal pests |
MX2014014341A (es) | 2012-05-24 | 2015-07-06 | Basf Se | Compuestos de n-tio-antranilamida y sus usos como plaguicidas. |
WO2013186089A2 (en) | 2012-06-14 | 2013-12-19 | Basf Se | Pesticidal methods using substituted 3-pyridyl thiazole compounds and derivatives for combating animal pests |
WO2014005982A1 (de) | 2012-07-05 | 2014-01-09 | Bayer Cropscience Ag | Insektizide und fungizide wirkstoffkombinationen |
CN104768378A (zh) | 2012-10-01 | 2015-07-08 | 巴斯夫欧洲公司 | N-硫代-邻氨基苯甲酰胺化合物在栽培植物上的用途 |
EP2903439A1 (en) | 2012-10-01 | 2015-08-12 | Basf Se | Method of controlling ryanodine-modulator insecticide resistant insects |
WO2014053407A1 (en) | 2012-10-01 | 2014-04-10 | Basf Se | N-thio-anthranilamide compounds and their use as pesticides |
WO2014053401A2 (en) | 2012-10-01 | 2014-04-10 | Basf Se | Method of improving plant health |
EP2903438A1 (en) | 2012-10-01 | 2015-08-12 | Basf Se | Pesticidally active mixtures comprising anthranilamide compounds |
WO2014053403A1 (en) | 2012-10-01 | 2014-04-10 | Basf Se | Method of controlling insecticide resistant insects |
WO2014053405A1 (en) | 2012-10-01 | 2014-04-10 | Basf Se | Pesticidally active mixtures comprising anthranilamide compounds |
BR112015011777B1 (pt) | 2012-11-22 | 2019-09-24 | Basf Corporation | Mistura sinérgica, kit para preparar uma composição pesticida útil, composição pesticida e método para proteger material de propagação vegetal |
PL2922399T3 (pl) | 2012-11-22 | 2020-11-02 | Basf Corporation | Mieszaniny szkodnikobójcze |
WO2014079804A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079764A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079770A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079774A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079841A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079772A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079820A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Use of anthranilamide compounds for reducing insect-vectored viral infections |
WO2014079766A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079813A1 (en) | 2012-11-23 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079752A1 (en) | 2012-11-23 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014090700A1 (en) | 2012-12-14 | 2014-06-19 | Basf Se | Malononitrile compounds for controlling animal pests |
EP2938611A1 (en) | 2012-12-27 | 2015-11-04 | Basf Se | 2-(pyridin-3-yl)-5-hetaryl-thiazole compounds carrying an imine or imine-derived substituent for combating invertebrate pests |
WO2014128136A1 (en) | 2013-02-20 | 2014-08-28 | Basf Se | Anthranilamide compounds and their use as pesticides |
BR112015026357A2 (pt) * | 2013-04-19 | 2017-07-25 | Basf Se | compostos, composição agrícola ou veterinária, métodos para o combate ou controle das pragas, para a proteção de vegetais, para a proteção do material de propagação e para o tratamento de animais e utilização de um composto |
PL2907390T3 (pl) * | 2013-05-27 | 2017-09-29 | Meiji Seika Pharma Co., Ltd. | Środki zwalczające pasożyty pszczół miodnych i sposób zwalczania pasożytów pszczół miodnych z ich użyciem |
BR112015031439A2 (pt) | 2013-06-21 | 2017-07-25 | Basf Se | métodos para o combate ou controle das pragas, para o tratamento, prevenção e proteção de culturas de soja, para o controle e proteção do material de propagação dos vegetais de soja, para o combate ou controle das pragas e utilização de um composto de fórmula i |
KR20160030565A (ko) | 2013-07-15 | 2016-03-18 | 바스프 에스이 | 살충제 화합물 |
WO2015028630A1 (en) * | 2013-08-30 | 2015-03-05 | Basf Se | N-substituted pyridylidene compounds and derivatives for combating animal pests |
JP2016531930A (ja) * | 2013-09-19 | 2016-10-13 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | N−アクリルイミノ複素環式化合物 |
AU2014323072B2 (en) | 2013-09-19 | 2018-01-18 | Basf Se | N-acylimino heterocyclic compounds |
UY35772A (es) | 2013-10-14 | 2015-05-29 | Bayer Cropscience Ag | Nuevos compuestos plaguicidas |
WO2015055554A1 (de) | 2013-10-14 | 2015-04-23 | Bayer Cropscience Ag | Wirkstoff für die saatgut- und bodenbehandlung |
WO2015055505A1 (de) * | 2013-10-14 | 2015-04-23 | Bayer Cropscience Ag | Wirkstoff zur bekämpfung von stinkwanzen |
WO2015055497A1 (en) | 2013-10-16 | 2015-04-23 | Basf Se | Substituted pesticidal pyrazole compounds |
JP6644681B2 (ja) | 2013-10-18 | 2020-02-12 | ビーエーエスエフ アグロケミカル プロダクツ ビー.ブイ. | 土壌及び種子施用における殺有害生物活性カルボキサミド誘導体の使用、並びに処理方法 |
WO2015059088A1 (de) | 2013-10-23 | 2015-04-30 | Bayer Cropscience Ag | Substituierte chinoxalin-derivate als schädlingsbekämpfungsmittel |
CA2929062A1 (en) | 2013-11-22 | 2015-05-28 | Basf Se | N-acylimino heterocyclic compounds |
JP2017502022A (ja) | 2013-12-18 | 2017-01-19 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | N−置換イミノ複素環式化合物 |
CN105829296A (zh) | 2013-12-18 | 2016-08-03 | 巴斯夫欧洲公司 | 带有亚胺衍生的取代基的唑类化合物 |
TW201540705A (zh) | 2014-01-03 | 2015-11-01 | 拜耳作物科學股份有限公司 | 做為殺蟲劑之新穎吡唑基雜芳基醯胺類 |
WO2015104422A1 (en) | 2014-01-13 | 2015-07-16 | Basf Se | Dihydrothiophene compounds for controlling invertebrate pests |
WO2015107133A1 (de) | 2014-01-20 | 2015-07-23 | Bayer Cropscience Ag | Chinolinderivate als insektizide und akarizide |
JP6398124B2 (ja) * | 2014-03-10 | 2018-10-03 | Meiji Seikaファルマ株式会社 | 2−アシルイミノピリジン誘導体の製造法 |
JP2017510588A (ja) * | 2014-03-27 | 2017-04-13 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 無脊椎有害生物を防除するためのn−アシルイミノ複素環式化合物 |
US9815792B2 (en) | 2014-04-02 | 2017-11-14 | Bayer Cropscience Aktiengesellschaft | Method for producing carboxamides |
JP6510559B2 (ja) | 2014-05-08 | 2019-05-08 | 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 | 殺線虫剤としてのピラゾロピリジンスルホンアミド類 |
ES2747810T3 (es) | 2014-06-05 | 2020-03-11 | Bayer Cropscience Ag | Compuestos bicíclicos como agentes para combatir parásitos |
WO2016001119A1 (de) * | 2014-07-01 | 2016-01-07 | Bayer Cropscience Aktiengesellschaft | Insektizide und fungizide wirkstoffkombinationen |
WO2016001122A1 (de) * | 2014-07-01 | 2016-01-07 | Bayer Cropscience Aktiengesellschaft | Methoden zur verbesserung des pflanzenwachstums |
WO2016001121A1 (en) * | 2014-07-01 | 2016-01-07 | Bayer Cropscience Aktiengesellschaft | Method for improved utilization of the production potential of transgenic plants |
WO2016001129A1 (de) | 2014-07-01 | 2016-01-07 | Bayer Cropscience Aktiengesellschaft | Verbesserte insektizide zusammensetzungen |
WO2016001120A1 (de) * | 2014-07-01 | 2016-01-07 | Bayer Cropscience Aktiengesellschaft | Insektizide wirkstoffkombinationen |
WO2016001125A1 (en) * | 2014-07-01 | 2016-01-07 | Bayer Cropscience Aktiengesellschaft | Active compound combinations and methods to protect the propagation material of plants |
TW201613866A (en) * | 2014-07-07 | 2016-04-16 | Bayer Cropscience Ag | Process for preparing fluorinated iminopyridine compounds |
JP2017521441A (ja) | 2014-07-15 | 2017-08-03 | バイエル・アニマル・ヘルス・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングBayer Animal Health Gmbh | 有害生物防除剤としてのアリール−トリアゾリルピリジン類 |
BR112017005140A2 (pt) | 2014-10-06 | 2018-01-23 | Basf Se | compostos, mistura, composição, métodos para a proteção de culturas e para o combate ou controle de praga de invertebrados, método não terapêutico para o tratamento de animais infestados ou infectados por parasitas e semente |
WO2016055096A1 (en) | 2014-10-07 | 2016-04-14 | Bayer Cropscience Ag | Method for treating rice seed |
BR112017009513A2 (pt) | 2014-11-06 | 2018-02-06 | Basf Se | utilização de um composto heterobicíclico, utilização dos compostos i, compostos, composição agrícola ou veterinária, método para o combate ou controle de pragas, método para a proteção de culturas e sementes |
AR102942A1 (es) | 2014-12-11 | 2017-04-05 | Bayer Cropscience Ag | Derivados de arilsulfuro y arilsulfóxido de cinco miembros c-n-conectados, como plaguicidas |
EP3081085A1 (en) | 2015-04-14 | 2016-10-19 | Bayer CropScience AG | Method for improving earliness in cotton |
UY36548A (es) | 2015-02-05 | 2016-06-01 | Bayer Cropscience Ag | Derivados heterocíclicos condensados bicíclicos sustituidos por 2-(het)arilo como pesticidas |
UY36547A (es) | 2015-02-05 | 2016-06-01 | Bayer Cropscience Ag | Derivados heterocíclicos condensados bicíclicos sustituidos por 2-(het)arilo como pesticidas |
WO2016124769A1 (en) | 2015-02-06 | 2016-08-11 | Basf Se | Pyrazole compounds as nitrification inhibitors |
TWI702212B (zh) | 2015-02-09 | 2020-08-21 | 德商拜耳作物科學股份有限公司 | 作為除害劑之經取代的2-硫基咪唑基羧醯胺類 |
BR112017015061B1 (pt) | 2015-02-11 | 2022-09-27 | Basf Se | Mistura pesticida compreendendo um composto ativo de fórmula ia e broflanilida |
AU2016231174B2 (en) | 2015-03-10 | 2020-09-10 | Bayer Animal Health Gmbh | Pyrazolyl-derivatives as pest control agents |
US11064696B2 (en) | 2015-04-07 | 2021-07-20 | Basf Agrochemical Products B.V. | Use of an insecticidal carboxamide compound against pests on cultivated plants |
EP3280716B1 (de) | 2015-04-08 | 2020-02-12 | Bayer CropScience AG | Imidazo[1,2-a]pyridin-2-yl-derivate als schädlingsbekämpfungsmittel und deren zwischenprodukte |
WO2016174049A1 (en) | 2015-04-30 | 2016-11-03 | Bayer Animal Health Gmbh | Anti-parasitic combinations including halogen-substituted compounds |
CA2983964A1 (en) | 2015-05-12 | 2016-11-17 | Basf Se | Thioether compounds as nitrification inhibitors |
CN107835803A (zh) | 2015-05-13 | 2018-03-23 | 拜耳作物科学股份公司 | 杀昆虫的芳基吡咯烷、其制备方法及其作为试剂用于防治动物害虫的用途 |
WO2016198613A1 (en) | 2015-06-11 | 2016-12-15 | Basf Se | N-(thio)acylimino compounds |
WO2016198611A1 (en) | 2015-06-11 | 2016-12-15 | Basf Se | N-(thio)acylimino heterocyclic compounds |
MX2018000292A (es) | 2015-07-06 | 2018-04-20 | Bayer Cropscience Ag | Compuestos heterociclicos como pesticidas. |
WO2017016883A1 (en) | 2015-07-24 | 2017-02-02 | Basf Se | Process for preparation of cyclopentene compounds |
WO2017025419A2 (de) | 2015-08-07 | 2017-02-16 | Bayer Cropscience Aktiengesellschaft | 2-(het)aryl-substituierte kondensierte heterocyclen-derivate als schädlingsbekämpfungsmittel |
AU2016333498A1 (en) | 2015-10-02 | 2018-04-05 | Basf Se | Imino compounds with a 2-chloropyrimidin-5-yl substituent as pest-control agents |
PE20181198A1 (es) | 2015-10-26 | 2018-07-23 | Bayer Cropscience Ag | Derivados de heterociclos biciclicos condensados como agentes de control de plagas |
WO2017093163A1 (en) | 2015-11-30 | 2017-06-08 | Basf Se | Mixtures of cis-jasmone and bacillus amyloliquefaciens |
WO2017093180A1 (de) | 2015-12-01 | 2017-06-08 | Bayer Cropscience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
RU2018123928A (ru) | 2015-12-03 | 2020-01-13 | Байер Кропсайенс Акциенгезельшафт | Мезоионные галогенированные 3-(ацетил)-1-[(1,3-тиазол-5-ил)метил]-1н-имидазо[1,2-а]пиридин-4-иум-2-олатные производные и родственные соединения в качестве инсектицидов |
WO2017104692A1 (ja) * | 2015-12-15 | 2017-06-22 | Meiji Seikaファルマ株式会社 | シロアリ防除剤 |
KR20180098631A (ko) | 2015-12-29 | 2018-09-04 | 메이지 세이카 파루마 가부시키가이샤 | 이미노피리딘 유도체를 함유하는 유해 생물 방제용 조성물 |
KR20180107142A (ko) | 2016-02-11 | 2018-10-01 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 해충 방제제로서의 치환된 2-옥시이미다졸릴-카르복스아미드 |
CN109071506B (zh) | 2016-02-11 | 2021-03-02 | 拜耳作物科学股份公司 | 作为有害生物防治剂的取代的2-(杂)芳基咪唑基羧酰胺 |
WO2017144341A1 (de) | 2016-02-23 | 2017-08-31 | Bayer Cropscience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
EP3210468A1 (de) | 2016-02-26 | 2017-08-30 | Bayer CropScience Aktiengesellschaft | Lösungsmittelfreie formulierungen von niedrig schmelzenden wirkstoffen |
EP3426660A1 (en) | 2016-03-09 | 2019-01-16 | Basf Se | Spirocyclic derivatives |
BR112018068042A2 (pt) | 2016-03-11 | 2019-01-08 | Basf Se | métodos para controlar pragas de plantas, material de propagação de planta e uso de um ou mais compostos de fórmula i |
EP3429355B1 (de) | 2016-03-15 | 2020-02-05 | Bayer CropScience AG | Substituierte sulfonylamide zur bekämpfung tierischer schädlinge |
EP3429997A1 (de) | 2016-03-16 | 2019-01-23 | Bayer CropScience Aktiengesellschaft | N-(cyanbenzyl)-6-(cyclopropylcarbonylamino)-4-(phenyl)-pyridin-2-carboxamid-derivate und verwandte verbindungen als pestizide pflanzenschutzmittel |
KR102411744B1 (ko) | 2016-04-01 | 2022-06-21 | 바스프 에스이 | 바이시클릭 화합물 |
WO2017174414A1 (de) | 2016-04-05 | 2017-10-12 | Bayer Cropscience Aktiengesellschaft | Naphthalin-derivate als schädlingsbekämpfungsmittel |
MX2018012544A (es) | 2016-04-15 | 2019-01-31 | Bayer Animal Health Gmbh | Nuevos derivados de pirazolopirimidina. |
AU2017256505B2 (en) | 2016-04-25 | 2021-02-18 | Bayer Cropscience Aktiengesellschaft | Substituted 2-alkylimidazolyl-carboxamides as pest control agents |
EP3241830A1 (de) | 2016-05-04 | 2017-11-08 | Bayer CropScience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2017198449A1 (en) | 2016-05-15 | 2017-11-23 | Bayer Cropscience Nv | Method for increasing yield in brassicaceae |
EP3245865A1 (en) | 2016-05-17 | 2017-11-22 | Bayer CropScience Aktiengesellschaft | Method for increasing yield in brassicaceae |
WO2017198450A1 (en) | 2016-05-15 | 2017-11-23 | Bayer Cropscience Nv | Method for increasing yield in maize |
WO2017198453A1 (en) | 2016-05-16 | 2017-11-23 | Bayer Cropscience Nv | Method for increasing yield in potato, tomato or alfalfa |
WO2017198452A1 (en) | 2016-05-16 | 2017-11-23 | Bayer Cropscience Nv | Method for increasing yield in soybean |
WO2017198454A1 (en) | 2016-05-17 | 2017-11-23 | Bayer Cropscience Nv | Method for increasing yield in cotton |
WO2017198455A2 (en) | 2016-05-17 | 2017-11-23 | Bayer Cropscience Nv | Method for increasing yield in beta spp. plants |
WO2017198451A1 (en) | 2016-05-17 | 2017-11-23 | Bayer Cropscience Nv | Method for increasing yield in small grain cereals such as wheat and rice |
WO2017198588A1 (en) | 2016-05-18 | 2017-11-23 | Basf Se | Capsules comprising benzylpropargylethers for use as nitrification inhibitors |
US10653135B2 (en) | 2016-07-11 | 2020-05-19 | Covestro Llc | Methods for treating seeds with an aqueous composition and seeds treated therewith |
US10750750B2 (en) | 2016-07-11 | 2020-08-25 | Covestro Llc | Aqueous compositions for treating seeds, seeds treated therewith, and methods for treating seeds |
US10653136B2 (en) | 2016-07-11 | 2020-05-19 | Covestro Llc | Aqueous compositions for treating seeds, seeds treated therewith, and methods for treating seeds |
JP2019522671A (ja) | 2016-07-12 | 2019-08-15 | 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 | 殺虫剤としての二環式化合物 |
CA3031139A1 (en) | 2016-07-19 | 2018-01-25 | Bayer Cropscience Aktiengesellschaft | Condensed bicyclic heterocycle derivatives as pest control agents |
EA039895B1 (ru) | 2016-07-29 | 2022-03-24 | Байер Кропсайенс Акциенгезельшафт | Способ обработки семян до посева, препарат для обработки семян, состоящий из спор p.bilaii и порошка талька, семена, обработанные указанным препаратом, способ получения указанного препарата и его применение для обработки семян |
AR109107A1 (es) | 2016-07-29 | 2018-10-31 | Bayer Cropscience Ag | Compuestos halógeno(tio)acilo sustituidos |
PE20190629A1 (es) | 2016-08-10 | 2019-04-26 | Bayer Cropscience Ag | 2-heterociclilimidazolilcarboxamidas sustituidas como pesticidas |
PE20190800A1 (es) | 2016-08-15 | 2019-06-10 | Bayer Cropscience Ag | Derivados del heterociclo biciclico condensado como agentes de control de plagas |
WO2018052115A1 (ja) * | 2016-09-16 | 2018-03-22 | Meiji Seikaファルマ株式会社 | 有害生物防除剤の最適化製造法 |
US10611779B2 (en) | 2016-09-19 | 2020-04-07 | Bayer Cropscience Aktiengesellschaft | Fused bicyclic heterocycle derivatives as pesticides |
KR102477315B1 (ko) | 2016-10-06 | 2022-12-13 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 해충 방제제로서의 2-(헤트)아릴-치환된 융합 비사이클릭 헤테로사이클 유도체 |
WO2018065288A1 (de) | 2016-10-07 | 2018-04-12 | Bayer Cropscience Aktiengesellschaft | 2-[2-phenyl-1-(sulfonylmethyl)vinyl]-imidazo[4,5-b]pyridin-derivate und verwandte verbindungen als schädlingsbekämpfungsmittel im pflanzenschutz |
JP2019532106A (ja) | 2016-10-14 | 2019-11-07 | ピーアイ インダストリーズ リミテッドPi Industries Ltd | 望ましくない植物病原性微生物と戦うことで作物を保護するための4−置換フェニルアミン誘導体およびその使用 |
US20190367445A1 (en) | 2016-10-14 | 2019-12-05 | Pi Industries Ltd. | 4-amino substituted phenylamidine derivatives and their use to protect crops by fighting undesired phytopathogenic micoorganisms |
TW201822637A (zh) | 2016-11-07 | 2018-07-01 | 德商拜耳廠股份有限公司 | 用於控制動物害蟲的經取代磺醯胺類 |
SI3538512T1 (sl) | 2016-11-11 | 2021-09-30 | Bayer Animal Health Gmbh | Novi antihelmintični kinolin-3-karboksamidni derivati |
EP3544978B1 (de) | 2016-11-23 | 2020-11-04 | Bayer CropScience Aktiengesellschaft | 2-[3-(alkylsulfonyl)-2h-indazol-2-yl]-3h-imidazo[4,5-b]pyridin-derivate und ähnliche verbindungen als schädlingsbekämpfungsmittel |
EP3400801A1 (en) | 2017-05-10 | 2018-11-14 | Bayer CropScience Aktiengesellschaft | Plant health effect of purpureocillium lilacinum |
JP2020502110A (ja) | 2016-12-16 | 2020-01-23 | バイエル・アクチエンゲゼルシヤフト | 殺虫剤として使用するためのメソイオン性イミダゾピリジン類 |
US20190382358A1 (en) | 2016-12-16 | 2019-12-19 | Bayer Cropscience Aktiengesellschaft | Heterocyclic compounds as pesticides |
WO2018108671A1 (en) | 2016-12-16 | 2018-06-21 | Basf Se | Pesticidal compounds |
WO2018116072A1 (en) | 2016-12-20 | 2018-06-28 | Pi Industries Ltd. | Heterocyclic compounds |
WO2018116073A1 (en) | 2016-12-21 | 2018-06-28 | Pi Industries Ltd. | 1, 2, 3-thiadiazole compounds and their use as crop protecting agent |
UY37557A (es) | 2017-01-10 | 2018-07-31 | Bayer Ag | Derivados heterocíclicos como pesticidas |
KR102515694B1 (ko) | 2017-01-10 | 2023-03-29 | 바이엘 악티엔게젤샤프트 | 해충 방제제로서의 헤테로사이클 유도체 |
CA3050864A1 (en) | 2017-01-26 | 2018-08-02 | Mitsui Chemicals Agro, Inc. | Pyridone compounds and agricultural and horticultural fungicides containing the same as active ingredients |
WO2018138050A1 (de) | 2017-01-26 | 2018-08-02 | Bayer Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
TW201833107A (zh) | 2017-02-06 | 2018-09-16 | 德商拜耳廠股份有限公司 | 作為殺蟲劑之經2-(雜)芳基取代的稠合雜環衍生物 |
EP3369320A1 (de) | 2017-03-02 | 2018-09-05 | Bayer CropScience Aktiengesellschaft | Wirkstoff zur bekämpfung von wanzen |
WO2018162312A1 (en) | 2017-03-10 | 2018-09-13 | Basf Se | Spirocyclic derivatives |
WO2018166855A1 (en) | 2017-03-16 | 2018-09-20 | Basf Se | Heterobicyclic substituted dihydroisoxazoles |
AU2018234204B2 (en) | 2017-03-17 | 2023-07-27 | Meiji Seika Pharma Co., Ltd. | Mesostigmata mite control agent |
MX2019011626A (es) | 2017-03-28 | 2019-12-05 | Basf Se | Compuestos plaguicidas. |
CN110461854A (zh) | 2017-03-31 | 2019-11-15 | 巴斯夫欧洲公司 | 制备手性2,3-二氢噻唑并[3,2-a]嘧啶-4-鎓化合物的方法 |
WO2018177993A1 (de) | 2017-03-31 | 2018-10-04 | Bayer Cropscience Aktiengesellschaft | Pyrazole zur bekämpfung von arthropoden |
EP4298908A3 (de) | 2017-03-31 | 2024-03-20 | Bayer Animal Health GmbH | Trizyklische carboxamide zur bekämpfung von arthropoden |
CA3059702A1 (en) | 2017-04-10 | 2018-10-18 | Mitsui Chemicals Agro, Inc. | Pyridone compounds and agricultural and horticultural fungicides containing the same as active ingredients |
CA3059675A1 (en) | 2017-04-10 | 2018-10-18 | Mitsui Chemicals Agro, Inc. | Pyridone compounds and agricultural and horticultural fungicides comprising the same as active ingredients |
CN110234627B (zh) | 2017-04-11 | 2023-09-01 | 三井化学植保株式会社 | 吡啶酮化合物及以吡啶酮化合物作为有效成分的农园艺用杀菌剂 |
BR112019021356A2 (pt) | 2017-04-12 | 2020-05-05 | Bayer Ag | imidazopiridinas mesoiônicas para uso como inseticidas |
WO2018192793A1 (en) | 2017-04-20 | 2018-10-25 | Basf Se | Substituted rhodanine derivatives |
RU2019136993A (ru) | 2017-04-20 | 2021-05-20 | Пи Индастриз Лтд. | Новые соединения фениламина |
US10993439B2 (en) | 2017-04-21 | 2021-05-04 | Bayer Aktiengesellschaft | Mesoionic imidazopyridines as insecticides |
EP3615540B1 (de) | 2017-04-24 | 2022-04-27 | Bayer Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
CN110582492A (zh) | 2017-04-26 | 2019-12-17 | 巴斯夫欧洲公司 | 作为农药的取代的琥珀酰亚胺衍生物 |
TWI782983B (zh) | 2017-04-27 | 2022-11-11 | 德商拜耳廠股份有限公司 | 雜芳基苯基胺基喹啉及類似物 |
CN110536892B (zh) | 2017-04-27 | 2023-05-12 | 拜耳动物保健有限责任公司 | 新的二环吡唑衍生物 |
JP7119003B2 (ja) | 2017-05-02 | 2022-08-16 | バイエル・アクチエンゲゼルシヤフト | 有害生物防除剤としての2-(ヘタ)アリール置換縮合二環式ヘテロ環式誘導体 |
WO2018202501A1 (de) | 2017-05-02 | 2018-11-08 | Bayer Aktiengesellschaft | 2-(het)aryl-substituierte kondensierte heterocyclen-derivate als schädlingsbekämpfungsmittel |
JP2020518589A (ja) | 2017-05-03 | 2020-06-25 | バイエル・アクチエンゲゼルシヤフト | トリ置換シリルベンジルベンゾイミダゾール類及び類縁体 |
WO2018202706A1 (en) | 2017-05-03 | 2018-11-08 | Bayer Aktiengesellschaft | Trisubstitutedsilylheteroaryloxyquinolines and analogues |
EP3619197A1 (en) | 2017-05-03 | 2020-03-11 | Bayer Aktiengesellschaft | Trisubstitutedsilylmethylphenoxyquinolines and analogues |
WO2018202525A1 (en) | 2017-05-04 | 2018-11-08 | Bayer Cropscience Aktiengesellschaft | Phenoxyethanamine derivatives for controlling pests |
SI3619196T1 (sl) | 2017-05-04 | 2022-10-28 | Bayer Cropscience Aktiengesellschaft | 2-((2-(feniloksimetil)piridin-5-il)oksi)-etanaminski derivati in sorodne spojine kot sredstva za zatiranje škodljivcev, npr. za zaščito rastlin |
AU2018266990B2 (en) | 2017-05-10 | 2022-01-27 | Basf Se | Bicyclic pesticidal compounds |
WO2018224455A1 (en) | 2017-06-07 | 2018-12-13 | Basf Se | Substituted cyclopropyl derivatives |
WO2018225829A1 (ja) | 2017-06-08 | 2018-12-13 | 三井化学アグロ株式会社 | ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤 |
CN110770235A (zh) | 2017-06-16 | 2020-02-07 | 巴斯夫欧洲公司 | 用于防除动物害虫的介离子咪唑鎓化合物和衍生物 |
US11542280B2 (en) | 2017-06-19 | 2023-01-03 | Basf Se | Substituted pyrimidinium compounds and derivatives for combating animal pests |
WO2018234488A1 (en) | 2017-06-23 | 2018-12-27 | Basf Se | SUBSTITUTED CYCLOPROPYL DERIVATIVES |
EP3615527B1 (en) | 2017-06-30 | 2024-03-06 | Elanco Animal Health GmbH | New azaquinoline derivatives |
WO2019007891A1 (de) | 2017-07-06 | 2019-01-10 | Bayer Aktiengesellschaft | Insektizide wirkstoffkombinationen |
WO2019007887A1 (de) | 2017-07-06 | 2019-01-10 | Bayer Aktiengesellschaft | Insektizide und fungizide wirkstoffkombinationen |
WO2019007888A1 (de) | 2017-07-06 | 2019-01-10 | Bayer Aktiengesellschaft | Insektizide wirkstoffkombinationen |
EP3284739A1 (de) | 2017-07-19 | 2018-02-21 | Bayer CropScience Aktiengesellschaft | Substituierte (het)arylverbindungen als schädlingsbekämpfungsmittel |
EP3634959A1 (en) | 2017-08-04 | 2020-04-15 | Bayer Animal Health GmbH | Quinoline derivatives for treating infections with helminths |
BR112020003109A2 (pt) | 2017-08-17 | 2020-08-04 | Bayer Cropscience Lp | composições dispersíveis em fertilizantes líquidos e métodos para as mesmas |
KR102600330B1 (ko) | 2017-08-22 | 2023-11-10 | 바이엘 악티엔게젤샤프트 | 해충 방제제로서의 헤테로시클렌 유도체 |
WO2019042932A1 (en) | 2017-08-31 | 2019-03-07 | Basf Se | METHOD FOR CONTROLLING RICE PARASITES IN RICE |
EP3453706A1 (en) | 2017-09-08 | 2019-03-13 | Basf Se | Pesticidal imidazole compounds |
AU2018335796A1 (en) | 2017-09-20 | 2020-05-07 | Mitsui Chemicals Agro, Inc. | Prolonged ectoparasite-controlling agent for animal |
CN117430622A (zh) | 2017-10-04 | 2024-01-23 | 拜耳公司 | 用作害虫防治剂的杂环化合物的衍生物 |
WO2019072906A1 (en) | 2017-10-13 | 2019-04-18 | Basf Se | IMIDAZOLIDINE PYRIMIDINIUM COMPOUNDS FOR CONTROL OF HARMFUL ANIMALS |
EP3473103A1 (de) | 2017-10-17 | 2019-04-24 | Bayer AG | Wässrige suspensionskonzentrate auf basis von 2-[(2,4-dichlorphenyl)-methyl]-4,4'-dimethyl-3-isoxazolidinon |
PT3697217T (pt) | 2017-10-18 | 2021-10-14 | Bayer Ag | Combinações de composto ativo que têm propriedades inseticidas/acaricidas |
CN111246742B (zh) | 2017-10-18 | 2022-09-23 | 拜耳公司 | 具有杀虫/杀螨特性的活性化合物结合物 |
WO2019076749A1 (en) | 2017-10-18 | 2019-04-25 | Bayer Aktiengesellschaft | COMBINATIONS OF ACTIVE COMPOUNDS HAVING INSECTICIDAL / ACARICIDE PROPERTIES |
AR113444A1 (es) | 2017-10-18 | 2020-05-06 | Bayer Ag | Combinaciones de compuestos activos con propiedades insecticidas / acaricidas |
MX2020003958A (es) | 2017-10-18 | 2020-08-03 | Bayer Ag | Combinaciones de compuestos activos con propiedades insecticidas/acaricidas. |
EP3473100A1 (en) | 2017-10-18 | 2019-04-24 | Bayer Aktiengesellschaft | Active compound combinations having insecticidal/acaricidal properties |
WO2019086009A1 (zh) | 2017-11-03 | 2019-05-09 | 华南农业大学 | 含氮稠合三环化合物及其作为农林业杀虫剂的应用 |
JP2021502402A (ja) | 2017-11-13 | 2021-01-28 | バイエル アクチェンゲゼルシャフトBayer Aktiengesellschaft | テトラゾリルプロピル誘導体および殺真菌剤としてのそれらの使用 |
CN111601802A (zh) | 2017-11-28 | 2020-08-28 | 拜耳股份有限公司 | 作为杀虫剂的杂环化合物 |
KR20200112816A (ko) | 2017-12-20 | 2020-10-05 | 피아이 인더스트리스 엘티디. | 불소알킬 화합물의 제조와 사용방법 |
WO2019121143A1 (en) | 2017-12-20 | 2019-06-27 | Basf Se | Substituted cyclopropyl derivatives |
TW201927768A (zh) | 2017-12-21 | 2019-07-16 | 德商拜耳廠股份有限公司 | 三取代矽基甲基雜芳氧基喹啉及類似物 |
JP7285844B2 (ja) | 2017-12-21 | 2023-06-02 | ビーエーエスエフ ソシエタス・ヨーロピア | 殺生物剤化合物 |
WO2019145140A1 (en) | 2018-01-09 | 2019-08-01 | Basf Se | Silylethynyl hetaryl compounds as nitrification inhibitors |
WO2019137995A1 (en) | 2018-01-11 | 2019-07-18 | Basf Se | Novel pyridazine compounds for controlling invertebrate pests |
EP3305786A3 (de) | 2018-01-22 | 2018-07-25 | Bayer CropScience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2019150311A1 (en) | 2018-02-02 | 2019-08-08 | Pi Industries Ltd. | 1-3 dithiol compounds and their use for the protection of crops from phytopathogenic microorganisms |
US20210009541A1 (en) | 2018-02-12 | 2021-01-14 | Bayer Aktiengesellschaft | Fungicidal oxadiazoles |
KR20200122353A (ko) | 2018-02-21 | 2020-10-27 | 바이엘 악티엔게젤샤프트 | 해충 방제제로서의 축합 바이시클릭 헤테로시클릭 유도체 |
WO2019162228A1 (en) | 2018-02-21 | 2019-08-29 | Bayer Aktiengesellschaft | 1-(5-substituted imidazol-1-yl)but-3-en derivatives and their use as fungicides |
WO2019166560A1 (en) | 2018-02-28 | 2019-09-06 | Basf Se | Use of n-functionalized alkoxy pyrazole compounds as nitrification inhibitors |
EP3758491A1 (en) | 2018-02-28 | 2021-01-06 | Basf Se | Use of pyrazole propargyl ethers as nitrification inhibitors |
IL297413B1 (en) | 2018-02-28 | 2024-03-01 | Basf Se | Use of Alkoxypyrazoles as nitrification inhibitors |
KR20200131269A (ko) | 2018-03-12 | 2020-11-23 | 바이엘 악티엔게젤샤프트 | 해충 방제제로서의 융합된 비시클릭 헤테로시클릭 유도체 |
WO2019175713A1 (en) | 2018-03-14 | 2019-09-19 | Basf Corporation | New catechol molecules and their use as inhibitors to p450 related metabolic pathways |
WO2019175712A1 (en) | 2018-03-14 | 2019-09-19 | Basf Corporation | New uses for catechol molecules as inhibitors to glutathione s-transferase metabolic pathways |
WO2019185413A1 (en) | 2018-03-27 | 2019-10-03 | Basf Se | Pesticidal substituted cyclopropyl derivatives |
WO2019197371A1 (en) | 2018-04-10 | 2019-10-17 | Bayer Aktiengesellschaft | Oxadiazoline derivatives |
WO2019197615A1 (de) | 2018-04-13 | 2019-10-17 | Bayer Aktiengesellschaft | Wirkstoffkombinationen mit fungiziden, insektiziden und akariziden eigenschaften |
WO2019197623A1 (de) | 2018-04-13 | 2019-10-17 | Bayer Aktiengesellschaft | Wirkstoffkombinationen mit insektiziden, nematiziden und akariziden eigenschaften |
UY38184A (es) | 2018-04-17 | 2019-10-31 | Bayer Ag | Compuestos heteroarilo-triazol y heteroarilo-tetrazol novedosos como plaguicidas |
AU2019254616A1 (en) | 2018-04-20 | 2020-10-08 | Bayer Aktiengesellschaft | Heteroaryl-triazole and heteroaryl-tetrazole compounds as pesticides |
MX2020011061A (es) | 2018-04-20 | 2020-11-06 | Bayer Ag | Derivados de heterocicleno como agentes para el control de plagas. |
CN108503559B (zh) * | 2018-04-23 | 2021-10-01 | 上海诗丹德生物技术有限公司 | 辣椒碱卤代衍生物的合成及其应用 |
MX2020011873A (es) | 2018-05-09 | 2021-01-20 | Bayer Animal Health Gmbh | Nuevos derivados de quinolina. |
JP7433244B2 (ja) | 2018-05-15 | 2024-02-19 | ビーエーエスエフ ソシエタス・ヨーロピア | ベンズピリモキサン及びオキサゾスルフィルを含む混合物並びにその使用及び施用方法 |
WO2019224092A1 (en) | 2018-05-22 | 2019-11-28 | Basf Se | Pesticidally active c15-derivatives of ginkgolides |
WO2019224143A1 (de) | 2018-05-24 | 2019-11-28 | Bayer Aktiengesellschaft | Wirkstoffkombinationen mit insektiziden, nematiziden und akariziden eigenschaften |
US20210267194A1 (en) | 2018-06-25 | 2021-09-02 | Bayer Cropscience Lp | Seed treatment method |
WO2020002189A1 (de) | 2018-06-27 | 2020-01-02 | Bayer Aktiengesellschaft | Wirkstoffkombinationen |
WO2020002472A1 (en) | 2018-06-28 | 2020-01-02 | Basf Se | Use of alkynylthiophenes as nitrification inhibitors |
PL3818051T3 (pl) | 2018-07-05 | 2022-11-28 | Bayer Aktiengesellschaft | Podstawione tiofenokarboksyamidy i analogi jako środki przeciwbakteryjne |
DK3826982T3 (da) | 2018-07-23 | 2024-01-22 | Basf Se | Anvendelse af en substitueret thiazolidinforbindelse som nitrificeringshæmmer |
WO2020020777A1 (en) | 2018-07-23 | 2020-01-30 | Basf Se | Use of substituted 2-thiazolines as nitrification inhibitors |
JP7291143B2 (ja) | 2018-07-25 | 2023-06-14 | 三井化学クロップ&ライフソリューション株式会社 | ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤 |
WO2020020813A1 (en) | 2018-07-25 | 2020-01-30 | Bayer Aktiengesellschaft | Fungicidal active compound combinations |
WO2020020816A1 (en) | 2018-07-26 | 2020-01-30 | Bayer Aktiengesellschaft | Novel triazole derivatives |
US20210321610A1 (en) | 2018-07-27 | 2021-10-21 | Bayer Aktiengesellschaft | Controlled release formulations for agrochemicals |
BR112021001633A2 (pt) | 2018-07-31 | 2021-05-04 | Bayer Aktiengesellschaft | formulações de liberação controlada com lignina para agroquímicos |
WO2020035826A1 (en) | 2018-08-17 | 2020-02-20 | Pi Industries Ltd. | 1,2-dithiolone compounds and use thereof |
EP3613736A1 (en) | 2018-08-22 | 2020-02-26 | Basf Se | Substituted glutarimide derivatives |
AR116314A1 (es) | 2018-09-13 | 2021-04-21 | Bayer Ag | Derivados heterocíclicos como plaguicidas |
JP2022500459A (ja) | 2018-09-17 | 2022-01-04 | バイエル・アクチエンゲゼルシヤフト | 穀物中の麦角病菌の制御と菌核の低減のための殺菌剤イソフクシプラムの使用 |
JP7301062B2 (ja) * | 2018-09-27 | 2023-06-30 | 三井化学クロップ&ライフソリューション株式会社 | 水性懸濁状農薬組成物 |
CA3112042A1 (en) | 2018-09-28 | 2020-04-02 | Basf Se | Method of controlling pests by seed treatment application of a mesoionic compound or mixture thereof |
EP3628156A1 (en) | 2018-09-28 | 2020-04-01 | Basf Se | Method for controlling pests of sugarcane, citrus, rapeseed, and potato plants |
EP3628157A1 (en) | 2018-09-28 | 2020-04-01 | Basf Se | Method of controlling insecticide resistant insects and virus transmission to plants |
EP3628158A1 (en) | 2018-09-28 | 2020-04-01 | Basf Se | Pesticidal mixture comprising a mesoionic compound and a biopesticide |
WO2020070050A1 (en) | 2018-10-01 | 2020-04-09 | Bayer Aktiengesellschaft | Fungicidal 5-substituted imidazol-1-yl carbinol derivatives |
AR116746A1 (es) | 2018-10-18 | 2021-06-09 | Bayer Ag | Heteroarilaminoquinolinas y análogos de las mismas |
AR116747A1 (es) | 2018-10-18 | 2021-06-09 | Bayer Ag | Piridilfenilaminoquinolinas y análogos de las mismas |
TW202028193A (zh) | 2018-10-20 | 2020-08-01 | 德商拜耳廠股份有限公司 | 氧雜環丁基苯氧基喹啉及類似物 |
EP3643705A1 (en) | 2018-10-24 | 2020-04-29 | Basf Se | Pesticidal compounds |
EP3643711A1 (en) | 2018-10-24 | 2020-04-29 | Bayer Animal Health GmbH | New anthelmintic compounds |
BR112021008491A2 (pt) | 2018-11-28 | 2021-08-03 | Basf Se | composto da fórmula i, composição, método de combate ou controle de pragas invertebradas, método de proteção de plantas em crescimento, semente, uso de composto da fórmula i e método de tratamento ou proteção de animais |
AR117169A1 (es) | 2018-11-28 | 2021-07-14 | Bayer Ag | (tio)amidas de piridazina como compuestos fungicidas |
EP3620052A1 (en) | 2018-12-12 | 2020-03-11 | Bayer Aktiengesellschaft | Use of phenoxypyridinyl-substituted (1h-1,2,4-triazol-1-yl)alcohols for controlling fungicidal diseases in maize |
AR117291A1 (es) | 2018-12-14 | 2021-07-28 | Syngenta Crop Protection Ag | Compuestos heterocíclicos de cianamida con actividad pesticida |
EP3898623A1 (en) | 2018-12-18 | 2021-10-27 | Basf Se | Substituted pyrimidinium compounds for combating animal pests |
US20220061323A1 (en) | 2018-12-18 | 2022-03-03 | Bayer Aktiengesellschaft | Active compound combinations having insecticidal/acaricidal properties |
AR117461A1 (es) | 2018-12-20 | 2021-08-04 | Bayer Ag | Compuestos de heterociclil piridazina como fungicidas |
CN113473860A (zh) | 2018-12-21 | 2021-10-01 | 拜耳公司 | 作为新的抗真菌剂的1,3,4-噁二唑及其衍生物 |
EP3669652A1 (en) | 2018-12-21 | 2020-06-24 | Bayer AG | Active compound combination |
EP3679791A1 (en) | 2019-01-08 | 2020-07-15 | Bayer AG | Active compound combinations |
EP3679789A1 (en) | 2019-01-08 | 2020-07-15 | Bayer AG | Active compound combinations |
EP3679792A1 (en) | 2019-01-08 | 2020-07-15 | Bayer AG | Active compound combinations |
EP3679790A1 (en) | 2019-01-08 | 2020-07-15 | Bayer AG | Active compound combinations |
EP3679793A1 (en) | 2019-01-08 | 2020-07-15 | Bayer AG | Active compound combinations |
EP3696177A1 (en) | 2019-02-12 | 2020-08-19 | Basf Se | Heterocyclic compounds for the control of invertebrate pests |
WO2020169526A1 (en) | 2019-02-18 | 2020-08-27 | Syngenta Crop Protection Ag | Pesticidally-active cyanamide heterocyclic compounds |
US20220132851A1 (en) | 2019-03-01 | 2022-05-05 | Bayer Aktiengesellschaft | Active compound combinations having insecticidal/acaricidal properties |
WO2020178307A1 (en) | 2019-03-05 | 2020-09-10 | Bayer Aktiengesellschaft | Active compound combination |
WO2020182929A1 (en) | 2019-03-13 | 2020-09-17 | Bayer Aktiengesellschaft | Substituted ureas and derivatives as new antifungal agents |
WO2020187656A1 (en) | 2019-03-15 | 2020-09-24 | Bayer Aktiengesellschaft | Active compound combinations having insecticidal/acaricidal properties |
EP3965575A1 (en) | 2019-05-10 | 2022-03-16 | Bayer CropScience LP | Active compound combinations |
EP3975718A1 (en) | 2019-05-29 | 2022-04-06 | Basf Se | Mesoionic imidazolium compounds and derivatives for combating animal pests |
EP3769623A1 (en) | 2019-07-22 | 2021-01-27 | Basf Se | Mesoionic imidazolium compounds and derivatives for combating animal pests |
WO2020256091A1 (ja) | 2019-06-21 | 2020-12-24 | Meiji Seikaファルマ株式会社 | フルピリミンを含有するイネ害虫防除用固形製剤 |
WO2020254494A1 (en) | 2019-06-21 | 2020-12-24 | Bayer Aktiengesellschaft | Fungicidal oxadiazoles |
WO2020254493A1 (en) | 2019-06-21 | 2020-12-24 | Bayer Aktiengesellschaft | Thienylhydroxyisoxazolines and derivatives thereof |
EP3986891A1 (en) | 2019-06-21 | 2022-04-27 | Bayer Aktiengesellschaft | Hydroxyisoxazolines and derivatives thereof |
EP3986874A1 (en) | 2019-06-21 | 2022-04-27 | Bayer Aktiengesellschaft | Benzylphenyl hydroxyisoxazolines and analogues as new antifungal agents |
BR112021025865A2 (pt) | 2019-06-21 | 2022-03-03 | Bayer Ag | Hidróxi-isoxazolinas e derivados das mesmas |
EP3986892A1 (en) | 2019-06-21 | 2022-04-27 | Bayer Aktiengesellschaft | Hydroxyisoxazolines and use thereof as fungicides |
EP3986877A1 (en) | 2019-06-21 | 2022-04-27 | Bayer Aktiengesellschaft | Hydroxyisoxazolines and derivatives thereof |
EP3986875A1 (en) | 2019-06-21 | 2022-04-27 | Bayer Aktiengesellschaft | Phenoxyphenyl hydroxyisoxazolines and analogues as new antifungal agents |
MA56441A (fr) | 2019-07-03 | 2022-05-11 | Bayer Ag | Thiophène carboxamides substitués et leurs dérivés comme microbicides |
EP3766879A1 (en) | 2019-07-19 | 2021-01-20 | Basf Se | Pesticidal pyrazole derivatives |
TW202120490A (zh) | 2019-07-30 | 2021-06-01 | 德商拜耳動物保健有限公司 | 新穎異喹啉衍生物 |
CN114615891A (zh) | 2019-09-11 | 2022-06-10 | 拜耳公司 | 基于2-[(2,4-二氯苯基)甲基]-4,4’-二甲基-3-异噁唑烷酮和苗前除草剂的高效制剂 |
EP4077317A1 (en) | 2019-12-20 | 2022-10-26 | Bayer Aktiengesellschaft | Thienyloxazolones and analogues |
CN115103840A (zh) | 2019-12-20 | 2022-09-23 | 拜耳公司 | 取代的噻吩甲酰胺、噻吩甲酸及其衍生物 |
EP3708565A1 (en) | 2020-03-04 | 2020-09-16 | Bayer AG | Pyrimidinyloxyphenylamidines and the use thereof as fungicides |
BR112022020315A2 (pt) | 2020-04-09 | 2022-12-13 | Bayer Animal Health Gmbh | Novos compostos anti-helmínticos |
WO2021209490A1 (en) | 2020-04-16 | 2021-10-21 | Bayer Aktiengesellschaft | Cyclaminephenylaminoquinolines as fungicides |
AR121829A1 (es) | 2020-04-16 | 2022-07-13 | Bayer Ag | Combinaciones de compuestos activos y composiciones fungicidas que los comprenden |
EP4135523A1 (en) | 2020-04-16 | 2023-02-22 | Bayer Aktiengesellschaft | Active compound combinations and fungicide compositions comprising those |
AR121830A1 (es) | 2020-04-16 | 2022-07-13 | Bayer Ag | Combinaciones de compuestos activos y composiciones fungicidas que los comprenden |
AU2021257573A1 (en) | 2020-04-16 | 2022-11-10 | Bayer Aktiengesellschaft | Active compound combinations and fungicide compositions comprising those |
WO2021209365A1 (en) | 2020-04-16 | 2021-10-21 | Bayer Aktiengesellschaft | Active compound combinations and fungicide compositions comprising those |
BR112022022595A2 (pt) | 2020-05-06 | 2022-12-20 | Bayer Ag | Piridina (tio)amidas como compostos fungicidas |
JP2023525349A (ja) | 2020-05-12 | 2023-06-15 | バイエル、アクチエンゲゼルシャフト | 殺真菌性化合物としてのトリアジンおよびピリミジン(チオ)アミド化合物 |
US20230192617A1 (en) | 2020-05-19 | 2023-06-22 | Bayer Cropscience Aktiengesellschaft | Azabicyclic(thio)amides as fungicidal compounds |
US20230278994A1 (en) | 2020-06-04 | 2023-09-07 | Bayer Aktiengesellschaft | Heterocyclyl pyrimidines and triazines as novel fungicides |
US20230234945A1 (en) | 2020-06-10 | 2023-07-27 | Bayer Aktiengesellschaft | Azabicyclyl-substituted heterocycles as fungicides |
CA3187296A1 (en) | 2020-06-18 | 2021-12-23 | Bayer Aktiengesellschaft | 3-(pyridazin-4-yl)-5,6-dihydro-4h-1,2,4-oxadiazine derivatives as fungicides for crop protection |
WO2021255091A1 (en) | 2020-06-19 | 2021-12-23 | Bayer Aktiengesellschaft | 1,3,4-oxadiazoles and their derivatives as fungicides |
BR112022025710A2 (pt) | 2020-06-19 | 2023-03-07 | Bayer Ag | 1,3,4-oxadiazol pirimidinas e 1,3,4-oxadiazol piridinas como fungicidas |
UY39275A (es) | 2020-06-19 | 2022-01-31 | Bayer Ag | 1,3,4-oxadiazol pirimidinas como fungicidas, procesos e intermediarios para su preparación, métodos de uso y usos de los mismos |
UY39276A (es) | 2020-06-19 | 2022-01-31 | Bayer Ag | Uso de compuestos de 1,3,4–oxadiazol–2–ilpirimidina para controlar microorganismos fitopatógenos, métodos de uso y composiciones. |
WO2022058327A1 (en) | 2020-09-15 | 2022-03-24 | Bayer Aktiengesellschaft | Substituted ureas and derivatives as new antifungal agents |
EP3915371A1 (en) | 2020-11-04 | 2021-12-01 | Bayer AG | Active compound combinations and fungicide compositions comprising those |
EP3915971A1 (en) | 2020-12-16 | 2021-12-01 | Bayer Aktiengesellschaft | Phenyl-s(o)n-phenylamidines and the use thereof as fungicides |
WO2022129190A1 (en) | 2020-12-18 | 2022-06-23 | Bayer Aktiengesellschaft | (hetero)aryl substituted 1,2,4-oxadiazoles as fungicides |
WO2022129196A1 (en) | 2020-12-18 | 2022-06-23 | Bayer Aktiengesellschaft | Heterobicycle substituted 1,2,4-oxadiazoles as fungicides |
WO2022129188A1 (en) | 2020-12-18 | 2022-06-23 | Bayer Aktiengesellschaft | 1,2,4-oxadiazol-3-yl pyrimidines as fungicides |
WO2022162129A1 (en) | 2021-01-28 | 2022-08-04 | Rhodia Operations | Method for treating rice seed with improved retention of agrochemical, micronutrient and colorant |
AR124796A1 (es) | 2021-02-02 | 2023-05-03 | Basf Se | Acción sinérgica de dcd y alcoxipirazoles como inhibidores de la nitrificación |
WO2022200364A1 (en) | 2021-03-25 | 2022-09-29 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
WO2022243521A1 (en) | 2021-05-21 | 2022-11-24 | Basf Se | Use of ethynylpyridine compounds as nitrification inhibitors |
CA3219128A1 (en) | 2021-05-21 | 2022-11-24 | Barbara Nave | Use of an n-functionalized alkoxy pyrazole compound as nitrification inhibitor |
WO2022268810A1 (en) | 2021-06-21 | 2022-12-29 | Basf Se | Metal-organic frameworks with pyrazole-based building blocks |
WO2022268813A1 (en) | 2021-06-24 | 2022-12-29 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
WO2022268815A1 (en) | 2021-06-24 | 2022-12-29 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
EP4148052A1 (en) | 2021-09-09 | 2023-03-15 | Bayer Animal Health GmbH | New quinoline derivatives |
WO2023078915A1 (en) | 2021-11-03 | 2023-05-11 | Bayer Aktiengesellschaft | Bis(hetero)aryl thioether (thio)amides as fungicidal compounds |
WO2023092050A1 (en) | 2021-11-20 | 2023-05-25 | Bayer Cropscience Lp | Beneficial combinations with recombinant bacillus cells expressing a serine protease |
WO2023099445A1 (en) | 2021-11-30 | 2023-06-08 | Bayer Aktiengesellschaft | Bis(hetero)aryl thioether oxadiazines as fungicidal compounds |
WO2023110656A1 (en) | 2021-12-15 | 2023-06-22 | Bayer Aktiengesellschaft | Spectroscopic solution for non-destructive quantification of one or more chemical substances in a matrix comprising coating and bulk material in a sample, such as coated seeds, using multivariate data analysis |
WO2023205602A1 (en) | 2022-04-18 | 2023-10-26 | Basf Corporation | High-load agricultural formulations and methods of making same |
WO2023203066A1 (en) | 2022-04-21 | 2023-10-26 | Basf Se | Synergistic action as nitrification inhibitors of dcd oligomers with alkoxypyrazole and its oligomers |
WO2024028243A1 (en) | 2022-08-02 | 2024-02-08 | Basf Se | Pyrazolo pesticidal compounds |
Family Cites Families (38)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2081393B1 (tr) * | 1969-12-23 | 1974-08-23 | Pharmacia Ab | |
US3867447A (en) * | 1972-08-25 | 1975-02-18 | Du Pont | Hydroxyguanidine O-carbamates |
AU5950573A (en) | 1972-08-25 | 1975-02-27 | Du Pont | Mono- and disubstituted hydroxyguanidines |
US4203988A (en) * | 1975-11-12 | 1980-05-20 | Merck & Co., Inc. | Pyridinyl ureas and pharmaceutical use |
US4206141A (en) * | 1978-12-15 | 1980-06-03 | Stauffer Chemical Company | Process for preparation of di-substituted cyanamides using quaternary salt catalysis |
JPH07121909B2 (ja) | 1986-09-10 | 1995-12-25 | 日本バイエルアグロケム株式会社 | 新規複素環式化合物及び殺虫剤 |
DE3639877A1 (de) | 1986-11-21 | 1988-05-26 | Bayer Ag | Hetarylalkyl substituierte 5- und 6-ringheterocyclen |
JPS63227552A (ja) * | 1987-03-13 | 1988-09-21 | Shionogi & Co Ltd | 2−フルオロエチル誘導体、その製造法およびそれを有効成分とする有害生物防除剤 |
JP2859301B2 (ja) * | 1989-07-08 | 1999-02-17 | 武田薬品工業株式会社 | 農園芸用殺虫組成物 |
HU207047B (en) * | 1989-11-07 | 1993-03-01 | Richter Gedeon Vegyeszet | Process for producing new pyridine derivatives and pharmaceutical copositions comprising same |
DE4021439A1 (de) * | 1989-12-14 | 1991-06-20 | Bayer Ag | 2-iminopyridin-derivate |
JPH0578323A (ja) | 1991-03-11 | 1993-03-30 | Nippon Soda Co Ltd | 新規なヘテロ環化合物、その製造方法及び殺虫剤 |
US5559108A (en) * | 1994-09-02 | 1996-09-24 | Bristol-Myers Squibb Company | Cephalosporin derivatives |
US5804686A (en) | 1996-01-19 | 1998-09-08 | Neurogen Corporation | fused pyrrolecarboxamides; a new class of GABA brain receptor ligands |
PT976737E (pt) | 1997-04-07 | 2009-07-31 | Nihon Nohyaku Co Ltd | Derivados de pirazole, processo para a sua preparação, produtos intermédios e agente de controlo de pragas que contém como ingrediente activo um desses derivados |
JP3190859B2 (ja) | 1997-07-29 | 2001-07-23 | 松下電器産業株式会社 | Cdma無線送信装置及びcdma無線受信装置 |
WO2000003975A2 (en) | 1998-07-16 | 2000-01-27 | Aventis Agriculture Ltd. | Aryl vinyl ether derivatives and their use as herbicides |
DE10063486A1 (de) | 2000-12-20 | 2002-07-04 | Bayer Ag | Dichlorpyridylmethylamide |
JP2003026661A (ja) | 2001-06-27 | 2003-01-29 | Sinon Corp | 複素環化合物 |
JP2005225860A (ja) | 2003-11-11 | 2005-08-25 | Ishihara Sangyo Kaisha Ltd | ビフェニル誘導体又はその塩、それらを有効成分として含有する有害生物防除剤 |
AR046698A1 (es) * | 2003-11-11 | 2005-12-21 | Ishihara Sangyo Kaisha | Derivado bifenilo o su sal, y pesticida que lo contienen como un ingrediente activo |
DE102004018953A1 (de) | 2004-04-20 | 2005-11-17 | Bayer Cropscience Gmbh | 4-Halogenalkylpyridin-3-sulfonsäureamide, Verfahren zu ihrer Herstellung, sie enthaltende Mittel und ihre Verwendung als Schädlingsbekämpfungsmittel |
DE102004041529A1 (de) * | 2004-08-27 | 2006-03-02 | Bayer Cropscience Gmbh | Herbizid-Kombinationen mit speziellen Ketoenolen |
US8604055B2 (en) * | 2004-12-31 | 2013-12-10 | Dr. Reddy's Laboratories Ltd. | Substituted benzylamino quinolines as cholesterol ester-transfer protein inhibitors |
WO2006138147A1 (en) * | 2005-06-13 | 2006-12-28 | Bayer Cropscience Ag | Pesticidal 5-di-(substituted)aminopyrazole derivatives |
BRPI0707091B8 (pt) * | 2006-03-10 | 2018-02-14 | Nissan Chemical Ind Ltd | composto de isoxalina e benzaldoxima substituído ou um sal do mesmo; pesticida, agroquímico, endo- ou ecto-parasiticidapara mamíferos ou pássaros, inseticida e acaricida contendo como um ou mais ingredientes ativos selecionados a partir do composto de isoxalina substituído e o sal do mesmo |
EP2030971B1 (en) | 2006-06-20 | 2011-10-12 | Ishihara Sangyo Kaisha, Ltd. | Pest control agent containing novel pyridyl-methanamine derivative or salt thereof |
JP5078323B2 (ja) | 2006-11-20 | 2012-11-21 | 株式会社カプコン | ゲーム装置、そのゲーム装置を実現するためのプログラム及び記録媒体 |
JP4985025B2 (ja) | 2007-03-28 | 2012-07-25 | 凸版印刷株式会社 | マイクロニードルチップ集合体、マイクロニードルチップ、医療器具、マイクロニードルチップ集合体製造方法およびマイクロニードルチップ製造方法 |
JP2008260691A (ja) * | 2007-04-10 | 2008-10-30 | Bayer Cropscience Ag | 殺虫性アリールイソオキサゾリン誘導体 |
JP2008266230A (ja) * | 2007-04-23 | 2008-11-06 | Bayer Cropscience Ag | 殺虫性アリールピロリジン類 |
US20100234363A1 (en) * | 2007-09-19 | 2010-09-16 | Institute Of Medicinal Molecular Design, Inc. | Heterocyclic derivative having inhibitory activity on type-i 11 data-hydroxysteroid dehydrogenase |
US7683064B2 (en) | 2008-02-05 | 2010-03-23 | Roche Palo Alto Llc | Inhibitors of Bruton's tyrosine kinase |
JP2011514315A (ja) * | 2008-02-07 | 2011-05-06 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | 殺虫性アリールピロリン類 |
JP2010138082A (ja) * | 2008-12-09 | 2010-06-24 | Nippon Soda Co Ltd | 環状アミン化合物またはその塩、並びに有害生物防除剤 |
KR20130132775A (ko) * | 2010-08-31 | 2013-12-05 | 메이지 세이카 파루마 가부시키가이샤 | 유해 생물 방제제 |
CN103781764B (zh) * | 2011-08-26 | 2016-07-20 | 明治制果药业株式会社 | 有害生物防除剂的制造法 |
CN112244015B (zh) * | 2012-02-29 | 2022-05-17 | 株式会社Mmag | 包括新型亚氨基吡啶衍生物的有害物防治组合物 |
-
2011
- 2011-08-26 KR KR1020137008197A patent/KR20130132775A/ko not_active Application Discontinuation
- 2011-08-26 MX MX2013002233A patent/MX363956B/es active IP Right Grant
- 2011-08-26 EP EP15175471.0A patent/EP2984930B1/en active Active
- 2011-08-26 UA UAA201303921A patent/UA109149C2/uk unknown
- 2011-08-26 AP AP2013006782A patent/AP3539A/xx active
- 2011-08-26 EP EP20140168966 patent/EP2789237A1/en not_active Withdrawn
- 2011-08-26 PE PE2013000357A patent/PE20131380A1/es active IP Right Grant
- 2011-08-26 NZ NZ722021A patent/NZ722021A/en unknown
- 2011-08-26 TR TR2018/16134T patent/TR201816134T4/tr unknown
- 2011-08-26 SG SG2013011887A patent/SG187883A1/en unknown
- 2011-08-26 PL PL13157997T patent/PL2631235T3/pl unknown
- 2011-08-26 MY MYPI2013700309A patent/MY163072A/en unknown
- 2011-08-26 HU HUE13157997A patent/HUE026428T2/en unknown
- 2011-08-26 MA MA35778A patent/MA34551B1/fr unknown
- 2011-08-26 EA EA201390320A patent/EA022848B1/ru unknown
- 2011-08-26 PL PL15175471T patent/PL2984930T3/pl unknown
- 2011-08-26 NZ NZ703964A patent/NZ703964A/en unknown
- 2011-08-26 CN CN201310150071.5A patent/CN103254125B/zh active Active
- 2011-08-26 KR KR1020137012387A patent/KR101442445B1/ko active IP Right Grant
- 2011-08-26 ES ES15175471.0T patent/ES2693089T3/es active Active
- 2011-08-26 EP EP11821689.4A patent/EP2628389A4/en not_active Withdrawn
- 2011-08-26 US US13/814,753 patent/US8957214B2/en active Active
- 2011-08-26 GE GEAP201113043A patent/GEP201706728B/en unknown
- 2011-08-26 NZ NZ607939A patent/NZ607939A/en unknown
- 2011-08-26 CR CR20200540A patent/CR20200540A/es unknown
- 2011-08-26 CR CR20190244A patent/CR20190244A/es unknown
- 2011-08-26 AU AU2011297160A patent/AU2011297160B2/en active Active
- 2011-08-26 BR BR112013004818A patent/BR112013004818B8/pt active IP Right Grant
- 2011-08-26 HU HUE15175471A patent/HUE040676T2/hu unknown
- 2011-08-26 CN CN201180023561.8A patent/CN102892290B/zh not_active Expired - Fee Related
- 2011-08-26 CN CN201410153185.XA patent/CN103960242B/zh active Active
- 2011-08-26 NZ NZ703862A patent/NZ703862A/en unknown
- 2011-08-26 EP EP13157997.1A patent/EP2631235B1/en active Active
- 2011-08-26 CU CU20130026A patent/CU24170B1/es active IP Right Grant
- 2011-08-26 CA CA2808144A patent/CA2808144C/en active Active
- 2011-08-26 EP EP15175467.8A patent/EP2959775A1/en not_active Withdrawn
- 2011-08-26 JP JP2012501048A patent/JPWO2012029672A1/ja not_active Ceased
- 2011-08-26 ES ES13157997.1T patent/ES2563461T3/es active Active
- 2011-08-26 WO PCT/JP2011/069352 patent/WO2012029672A1/ja active Application Filing
- 2011-08-30 TW TW104142934A patent/TWI554210B/zh active
- 2011-08-30 TW TW100131116A patent/TWI538620B/zh active
-
2012
- 2012-02-29 JP JP2012042723A patent/JP4993641B2/ja active Active
-
2013
- 2013-02-06 IL IL224592A patent/IL224592A/en active IP Right Grant
- 2013-02-07 US US13/761,306 patent/US9073866B2/en not_active Expired - Fee Related
- 2013-02-13 ZA ZA2013/01156A patent/ZA201301156B/en unknown
- 2013-02-22 DO DO2013000046A patent/DOP2013000046A/es unknown
- 2013-02-26 NI NI201300025A patent/NI201300025A/es unknown
- 2013-02-27 CL CL2013000570A patent/CL2013000570A1/es unknown
- 2013-03-06 CO CO13045134A patent/CO6680699A2/es unknown
- 2013-03-27 EC ECSP13012527 patent/ECSP13012527A/es unknown
- 2013-11-08 HK HK14101510.3A patent/HK1188595A1/zh unknown
-
2014
- 2014-05-13 IL IL232581A patent/IL232581A0/en unknown
- 2014-12-17 US US14/573,344 patent/US9328068B2/en active Active
-
2016
- 2016-03-25 US US15/080,971 patent/US9717242B2/en active Active
- 2016-10-12 CL CL2016002590A patent/CL2016002590A1/es unknown
-
2017
- 2017-06-27 US US15/634,284 patent/US10085449B2/en active Active
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
TR201816134T4 (tr) | Zararli kontrol ajani | |
JP5745704B2 (ja) | 新規イミノピリジン誘導体を含む有害生物防除用組成物 | |
JP6236396B2 (ja) | 2−イミノ基を有する含窒素ヘテロ環誘導体及びそれを含んでなる有害生物防除剤 | |
JP5649824B2 (ja) | 新規浸透移行性殺虫剤 | |
JPWO2010071218A1 (ja) | 16−ケトアスペルギルイミドを含む有害生物防除用組成物 | |
WO2010071219A1 (ja) | 16-ケトアスペルギルイミド類およびそれを有効成分として含有する有害生物防除剤 | |
AU2014250649A1 (en) | Noxious organism control agent | |
OA16334A (en) | Noxious organism control agent |