BG64417B1 - Пестицидни съединения, състави и метод за получаването им - Google Patents
Пестицидни съединения, състави и метод за получаването им Download PDFInfo
- Publication number
- BG64417B1 BG64417B1 BG102488A BG10248898A BG64417B1 BG 64417 B1 BG64417 B1 BG 64417B1 BG 102488 A BG102488 A BG 102488A BG 10248898 A BG10248898 A BG 10248898A BG 64417 B1 BG64417 B1 BG 64417B1
- Authority
- BG
- Bulgaria
- Prior art keywords
- compounds
- general formula
- alkyl
- same meanings
- methyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 136
- 239000000203 mixture Substances 0.000 title claims description 55
- 238000002360 preparation method Methods 0.000 title claims description 29
- 238000000034 method Methods 0.000 title claims description 17
- 230000000361 pesticidal effect Effects 0.000 title claims description 6
- -1 methylenedioxy Chemical group 0.000 claims abstract description 47
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 36
- 239000004480 active ingredient Substances 0.000 claims abstract description 35
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 31
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 15
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 12
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 10
- 150000002367 halogens Chemical class 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 5
- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 claims description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- 241000238421 Arthropoda Species 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 239000005906 Imidacloprid Substances 0.000 claims description 7
- 229940056881 imidacloprid Drugs 0.000 claims description 7
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 claims description 7
- 238000009472 formulation Methods 0.000 claims description 6
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 claims description 6
- 239000005658 Tebufenpyrad Substances 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- AMAGNAXREAGWSV-UHFFFAOYSA-N 3-(but-2-ynoxymethyl)-2,3-dihydro-1,4-benzodioxine Chemical compound C1=CC=C2OC(COCC#CC)COC2=C1 AMAGNAXREAGWSV-UHFFFAOYSA-N 0.000 claims description 4
- JGRBQLMBYFIVEZ-UHFFFAOYSA-N 5-(but-2-ynoxymethyl)-1,3-benzodioxole Chemical compound CC#CCOCC1=CC=C2OCOC2=C1 JGRBQLMBYFIVEZ-UHFFFAOYSA-N 0.000 claims description 4
- DRJWVLPDDQUFGP-UHFFFAOYSA-N 5-[but-2-ynoxy(phenyl)methyl]-1,3-benzodioxole Chemical compound C=1C=C2OCOC2=CC=1C(OCC#CC)C1=CC=CC=C1 DRJWVLPDDQUFGP-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- 239000005899 Fipronil Substances 0.000 claims description 4
- XEGGRYVFLWGFHI-UHFFFAOYSA-N bendiocarb Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)O2 XEGGRYVFLWGFHI-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- 229940013764 fipronil Drugs 0.000 claims description 4
- JYQUHIFYBATCCY-UHFFFAOYSA-N quinalphos Chemical compound C1=CC=CC2=NC(OP(=S)(OCC)OCC)=CN=C21 JYQUHIFYBATCCY-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- HMDKNQJXXKUELV-UHFFFAOYSA-N 2,2-dimethyl-7-pent-3-ynoxy-3h-1-benzofuran Chemical compound CC#CCCOC1=CC=CC2=C1OC(C)(C)C2 HMDKNQJXXKUELV-UHFFFAOYSA-N 0.000 claims description 3
- YHFTXIPQNBRRSS-CYBMUJFWSA-N 2-[(1r)-1-but-2-ynoxyethyl]naphthalene Chemical compound C1=CC=CC2=CC([C@@H](C)OCC#CC)=CC=C21 YHFTXIPQNBRRSS-CYBMUJFWSA-N 0.000 claims description 3
- 239000005944 Chlorpyrifos Substances 0.000 claims description 3
- SDKQRNRRDYRQKY-UHFFFAOYSA-N Dioxacarb Chemical compound CNC(=O)OC1=CC=CC=C1C1OCCO1 SDKQRNRRDYRQKY-UHFFFAOYSA-N 0.000 claims description 3
- QGLZXHRNAYXIBU-WEVVVXLNSA-N aldicarb Chemical compound CNC(=O)O\N=C\C(C)(C)SC QGLZXHRNAYXIBU-WEVVVXLNSA-N 0.000 claims description 3
- CJJOSEISRRTUQB-UHFFFAOYSA-N azinphos-methyl Chemical group C1=CC=C2C(=O)N(CSP(=S)(OC)OC)N=NC2=C1 CJJOSEISRRTUQB-UHFFFAOYSA-N 0.000 claims description 3
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 3
- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 claims description 3
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 claims description 3
- JLYXXMFPNIAWKQ-GNIYUCBRSA-N gamma-hexachlorocyclohexane Chemical compound Cl[C@H]1[C@H](Cl)[C@@H](Cl)[C@@H](Cl)[C@H](Cl)[C@H]1Cl JLYXXMFPNIAWKQ-GNIYUCBRSA-N 0.000 claims description 3
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N gamma-hexachlorocyclohexane Natural products ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 claims description 3
- 229960002809 lindane Drugs 0.000 claims description 3
- 229960000490 permethrin Drugs 0.000 claims description 3
- 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 claims description 3
- 229940108410 resmethrin Drugs 0.000 claims description 3
- VEMKTZHHVJILDY-FIWHBWSRSA-N resmethrin Chemical compound CC1(C)[C@H](C=C(C)C)C1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-FIWHBWSRSA-N 0.000 claims description 3
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 claims description 3
- XGWIJUOSCAQSSV-XHDPSFHLSA-N (S,S)-hexythiazox Chemical compound S([C@H]([C@@H]1C)C=2C=CC(Cl)=CC=2)C(=O)N1C(=O)NC1CCCCC1 XGWIJUOSCAQSSV-XHDPSFHLSA-N 0.000 claims description 2
- PCKNFPQPGUWFHO-SXBRIOAWSA-N (Z)-flucycloxuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC(C=C1)=CC=C1CO\N=C(C=1C=CC(Cl)=CC=1)\C1CC1 PCKNFPQPGUWFHO-SXBRIOAWSA-N 0.000 claims description 2
- IAKOZHOLGAGEJT-UHFFFAOYSA-N 1,1,1-trichloro-2,2-bis(p-methoxyphenyl)-Ethane Chemical compound C1=CC(OC)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(OC)C=C1 IAKOZHOLGAGEJT-UHFFFAOYSA-N 0.000 claims description 2
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 2
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims description 2
- RURQAJURNPMSSK-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3-{[2-(4-ethoxyphenyl)-3,3,3-trifluoropropoxy]methyl}benzene Chemical compound C1=CC(OCC)=CC=C1C(C(F)(F)F)COCC1=CC=CC(OC=2C=CC(Cl)=CC=2)=C1 RURQAJURNPMSSK-UHFFFAOYSA-N 0.000 claims description 2
- KAJRUHJCBCZULP-UHFFFAOYSA-N 1-cyclohepta-1,3-dien-1-ylcyclohepta-1,3-diene Chemical class C1CCC=CC=C1C1=CC=CCCC1 KAJRUHJCBCZULP-UHFFFAOYSA-N 0.000 claims description 2
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 claims description 2
- BOTNFCTYKJBUMU-UHFFFAOYSA-N 2-[4-(2-methylpropyl)piperazin-4-ium-1-yl]-2-oxoacetate Chemical compound CC(C)C[NH+]1CCN(C(=O)C([O-])=O)CC1 BOTNFCTYKJBUMU-UHFFFAOYSA-N 0.000 claims description 2
- SWBHWUYHHJCADA-UHFFFAOYSA-N 3-(2-chlorophenyl)-6-(2,6-difluorophenyl)-1,2,4,5-tetrazine Chemical compound FC1=CC=CC(F)=C1C1=NN=C(C=2C(=CC=CC=2)Cl)N=N1 SWBHWUYHHJCADA-UHFFFAOYSA-N 0.000 claims description 2
- MJGMFKLLOFXJII-UHFFFAOYSA-N 4-[4-(4-ethoxyphenyl)-4-methylpentyl]-1-fluoro-2-phenoxybenzene Chemical compound C1=CC(OCC)=CC=C1C(C)(C)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 MJGMFKLLOFXJII-UHFFFAOYSA-N 0.000 claims description 2
- CUPJCYZBIVNNRI-UHFFFAOYSA-N 5-(1-but-2-ynoxy-2-methylpropyl)-1,3-benzodioxole Chemical compound CC#CCOC(C(C)C)C1=CC=C2OCOC2=C1 CUPJCYZBIVNNRI-UHFFFAOYSA-N 0.000 claims description 2
- YRRKLBAKDXSTNC-UHFFFAOYSA-N Aldicarb sulfonyl Natural products CNC(=O)ON=CC(C)(C)S(C)(=O)=O YRRKLBAKDXSTNC-UHFFFAOYSA-N 0.000 claims description 2
- YRRKLBAKDXSTNC-WEVVVXLNSA-N Aldoxycarb Chemical compound CNC(=O)O\N=C\C(C)(C)S(C)(=O)=O YRRKLBAKDXSTNC-WEVVVXLNSA-N 0.000 claims description 2
- 239000005885 Buprofezin Substances 0.000 claims description 2
- 239000005490 Carbetamide Substances 0.000 claims description 2
- 239000005946 Cypermethrin Substances 0.000 claims description 2
- 239000005657 Fenpyroximate Substances 0.000 claims description 2
- 239000005661 Hexythiazox Substances 0.000 claims description 2
- VSNHCAURESNICA-UHFFFAOYSA-N Hydroxyurea Chemical class NC(=O)NO VSNHCAURESNICA-UHFFFAOYSA-N 0.000 claims description 2
- NISLLQUWIJASOV-UHFFFAOYSA-N N'-benzoyl-N-(tert-butyl)benzohydrazide Chemical compound C=1C=CC=CC=1C(=O)N(C(C)(C)C)NC(=O)C1=CC=CC=C1 NISLLQUWIJASOV-UHFFFAOYSA-N 0.000 claims description 2
- HRYILSDLIGTCOP-UHFFFAOYSA-N N-benzoylurea Chemical class NC(=O)NC(=O)C1=CC=CC=C1 HRYILSDLIGTCOP-UHFFFAOYSA-N 0.000 claims description 2
- 239000005950 Oxamyl Substances 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- 239000005663 Pyridaben Substances 0.000 claims description 2
- 239000005938 Teflubenzuron Substances 0.000 claims description 2
- 239000005942 Triflumuron Substances 0.000 claims description 2
- AMRQXHFXNZFDCH-SECBINFHSA-N [(2r)-1-(ethylamino)-1-oxopropan-2-yl] n-phenylcarbamate Chemical compound CCNC(=O)[C@@H](C)OC(=O)NC1=CC=CC=C1 AMRQXHFXNZFDCH-SECBINFHSA-N 0.000 claims description 2
- FZSVSABTBYGOQH-XFFZJAGNSA-N [(e)-(3,3-dimethyl-1-methylsulfanylbutan-2-ylidene)amino] n-methylcarbamate Chemical compound CNC(=O)O\N=C(C(C)(C)C)\CSC FZSVSABTBYGOQH-XFFZJAGNSA-N 0.000 claims description 2
- 150000003869 acetamides Chemical class 0.000 claims description 2
- IMIDOCRTMDIQIJ-UHFFFAOYSA-N aminocarb Chemical compound CNC(=O)OC1=CC=C(N(C)C)C(C)=C1 IMIDOCRTMDIQIJ-UHFFFAOYSA-N 0.000 claims description 2
- ONHBDDJJTDTLIR-UHFFFAOYSA-N azocyclotin Chemical compound C1CCCCC1[Sn](N1N=CN=C1)(C1CCCCC1)C1CCCCC1 ONHBDDJJTDTLIR-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- YFXPPSKYMBTNAV-UHFFFAOYSA-N bensultap Chemical compound C=1C=CC=CC=1S(=O)(=O)SCC(N(C)C)CSS(=O)(=O)C1=CC=CC=C1 YFXPPSKYMBTNAV-UHFFFAOYSA-N 0.000 claims description 2
- 150000008047 benzoylureas Chemical class 0.000 claims description 2
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- FOANIXZHAMJWOI-UHFFFAOYSA-N bromopropylate Chemical compound C=1C=C(Br)C=CC=1C(O)(C(=O)OC(C)C)C1=CC=C(Br)C=C1 FOANIXZHAMJWOI-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 229960005286 carbaryl Drugs 0.000 claims description 2
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 claims description 2
- JLQUFIHWVLZVTJ-UHFFFAOYSA-N carbosulfan Chemical compound CCCCN(CCCC)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 JLQUFIHWVLZVTJ-UHFFFAOYSA-N 0.000 claims description 2
- BIWJNBZANLAXMG-YQELWRJZSA-N chloordaan Chemical compound ClC1=C(Cl)[C@@]2(Cl)C3CC(Cl)C(Cl)C3[C@]1(Cl)C2(Cl)Cl BIWJNBZANLAXMG-YQELWRJZSA-N 0.000 claims description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 2
- WCMMILVIRZAPLE-UHFFFAOYSA-M cyhexatin Chemical compound C1CCCCC1[Sn](C1CCCCC1)(O)C1CCCCC1 WCMMILVIRZAPLE-UHFFFAOYSA-M 0.000 claims description 2
- 229960005424 cypermethrin Drugs 0.000 claims description 2
- 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 claims description 2
- 230000006378 damage Effects 0.000 claims description 2
- RDYMFSUJUZBWLH-SVWSLYAFSA-N endosulfan Chemical compound C([C@@H]12)OS(=O)OC[C@@H]1[C@]1(Cl)C(Cl)=C(Cl)[C@@]2(Cl)C1(Cl)Cl RDYMFSUJUZBWLH-SVWSLYAFSA-N 0.000 claims description 2
- 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 claims description 2
- HJUFTIJOISQSKQ-UHFFFAOYSA-N fenoxycarb Chemical compound C1=CC(OCCNC(=O)OCC)=CC=C1OC1=CC=CC=C1 HJUFTIJOISQSKQ-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- FRCCEHPWNOQAEU-UHFFFAOYSA-N heptachlor Chemical compound ClC1=C(Cl)C2(Cl)C3C=CC(Cl)C3C1(Cl)C2(Cl)Cl FRCCEHPWNOQAEU-UHFFFAOYSA-N 0.000 claims description 2
- RGNPBRKPHBKNKX-UHFFFAOYSA-N hexaflumuron Chemical compound C1=C(Cl)C(OC(F)(F)C(F)F)=C(Cl)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F RGNPBRKPHBKNKX-UHFFFAOYSA-N 0.000 claims description 2
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 claims description 2
- 150000002903 organophosphorus compounds Chemical class 0.000 claims description 2
- KZAUOCCYDRDERY-UHFFFAOYSA-N oxamyl Chemical compound CNC(=O)ON=C(SC)C(=O)N(C)C KZAUOCCYDRDERY-UHFFFAOYSA-N 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 2
- IOUNQDKNJZEDEP-UHFFFAOYSA-N phosalone Chemical compound C1=C(Cl)C=C2OC(=O)N(CSP(=S)(OCC)OCC)C2=C1 IOUNQDKNJZEDEP-UHFFFAOYSA-N 0.000 claims description 2
- QHOQHJPRIBSPCY-UHFFFAOYSA-N pirimiphos-methyl Chemical group CCN(CC)C1=NC(C)=CC(OP(=S)(OC)OC)=N1 QHOQHJPRIBSPCY-UHFFFAOYSA-N 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 150000003217 pyrazoles Chemical class 0.000 claims description 2
- 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 claims description 2
- 150000003222 pyridines Chemical class 0.000 claims description 2
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 claims description 2
- 150000003230 pyrimidines Chemical class 0.000 claims description 2
- 150000003233 pyrroles Chemical class 0.000 claims description 2
- 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 claims description 2
- WWJZWCUNLNYYAU-UHFFFAOYSA-N temephos Chemical compound C1=CC(OP(=S)(OC)OC)=CC=C1SC1=CC=C(OP(=S)(OC)OC)C=C1 WWJZWCUNLNYYAU-UHFFFAOYSA-N 0.000 claims description 2
- 150000003505 terpenes Chemical class 0.000 claims description 2
- 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 claims description 2
- 150000004905 tetrazines Chemical class 0.000 claims description 2
- 150000008334 thiadiazines Chemical class 0.000 claims description 2
- 150000003852 triazoles Chemical class 0.000 claims description 2
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 claims description 2
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 claims description 2
- VBNMRCZKYNKLSD-UHFFFAOYSA-N 1-(1-but-2-ynoxypropyl)naphthalene Chemical compound C1=CC=C2C(C(OCC#CC)CC)=CC=CC2=C1 VBNMRCZKYNKLSD-UHFFFAOYSA-N 0.000 claims 2
- YPAPSZNSDFPGNQ-UHFFFAOYSA-N 1-(but-2-ynoxymethyl)naphthalene Chemical compound C1=CC=C2C(COCC#CC)=CC=CC2=C1 YPAPSZNSDFPGNQ-UHFFFAOYSA-N 0.000 claims 2
- BNMTYJGGCUGZIH-UHFFFAOYSA-N 2-(but-2-ynoxymethyl)-1,3-dichlorobenzene Chemical compound CC#CCOCC1=C(Cl)C=CC=C1Cl BNMTYJGGCUGZIH-UHFFFAOYSA-N 0.000 claims 2
- 241000607479 Yersinia pestis Species 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 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 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/164—Unsaturated ethers containing six-membered aromatic rings
- C07C43/166—Unsaturated ethers containing six-membered aromatic rings having unsaturation outside the aromatic rings
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- A—HUMAN NECESSITIES
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- 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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/04—Oxygen or sulfur attached to an aliphatic side-chain of a carbocyclic ring system
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- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
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- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
- A01N31/16—Oxygen or sulfur directly attached to an aromatic ring system with two or more oxygen or sulfur atoms directly attached to the same aromatic ring system
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- A—HUMAN NECESSITIES
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- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
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- A—HUMAN NECESSITIES
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- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
- A01N33/18—Nitro compounds
- A01N33/20—Nitro compounds containing oxygen or sulfur attached to the carbon skeleton containing the nitro group
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- A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
- A01N35/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond
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- 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
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- 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
- A01N37/32—Cyclic imides of polybasic carboxylic acids or thio analogues thereof
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- A—HUMAN NECESSITIES
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/12—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings condensed with a carbocyclic ring
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- A—HUMAN NECESSITIES
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- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
- A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
- A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
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- A—HUMAN NECESSITIES
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- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/32—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/30—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the six-membered aromatic ring being part of a condensed ring system formed by two rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/65—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/17—Unsaturated ethers containing halogen
- C07C43/174—Unsaturated ethers containing halogen containing six-membered aromatic rings
- C07C43/176—Unsaturated ethers containing halogen containing six-membered aromatic rings having unsaturation outside the aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/18—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C43/188—Unsaturated ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/215—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring having unsaturation outside the six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
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- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Furan Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HU9503318A HU220697B1 (hu) | 1995-11-21 | 1995-11-21 | Arthropodicid hatóanyagok, eljárás előállításukra és ezeket a hatóanyagokat tartalmazó készítmények |
Publications (2)
Publication Number | Publication Date |
---|---|
BG102488A BG102488A (en) | 1999-04-30 |
BG64417B1 true BG64417B1 (bg) | 2005-01-31 |
Family
ID=10987379
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
BG102488A BG64417B1 (bg) | 1995-11-21 | 1998-05-26 | Пестицидни съединения, състави и метод за получаването им |
Country Status (33)
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US (1) | US6277867B1 (de) |
EP (1) | EP0862545B1 (de) |
JP (1) | JP3487863B2 (de) |
KR (1) | KR100439078B1 (de) |
CN (1) | CN1117055C (de) |
AR (1) | AR004969A1 (de) |
AT (1) | ATE242193T1 (de) |
AU (1) | AU710995C (de) |
BG (1) | BG64417B1 (de) |
BR (1) | BR9611643A (de) |
CA (1) | CA2238186A1 (de) |
CZ (1) | CZ154598A3 (de) |
DE (1) | DE69628580T2 (de) |
DK (1) | DK0862545T3 (de) |
EA (1) | EA002064B1 (de) |
EE (1) | EE9800140A (de) |
ES (1) | ES2202488T3 (de) |
HK (1) | HK1017667A1 (de) |
HR (1) | HRP960545B1 (de) |
HU (1) | HU220697B1 (de) |
IL (1) | IL124490A0 (de) |
MX (1) | MX9804017A (de) |
NO (1) | NO311426B1 (de) |
NZ (1) | NZ323003A (de) |
PL (1) | PL185691B1 (de) |
PT (1) | PT862545E (de) |
SI (1) | SI0862545T1 (de) |
SK (1) | SK66698A3 (de) |
TR (1) | TR199800901T2 (de) |
UA (1) | UA49864C2 (de) |
WO (1) | WO1997019040A2 (de) |
YU (1) | YU61896A (de) |
ZA (1) | ZA969733B (de) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
HU223972B1 (hu) * | 1997-05-14 | 2005-03-29 | AGRO-CHEMIE Növényvédőszer Gyártó, Értékesítő és Forgalmazó Kft. | Arthropodicid hatású (+/-)-1-(1-/but-2-inil-oxi/-etil)-3,4-dimetoxi-benzol (+) optikai izomerje, előállítása, hatóanyagként a vegyületet tartalmazó készítmény és alkalmazása |
FR2798928B1 (fr) * | 1999-09-29 | 2003-04-11 | Rhodia Chimie Sa | Procede de preparation d'ethers mixtes alcyniques substitues |
JP4474745B2 (ja) * | 1999-12-10 | 2010-06-09 | 住友化学株式会社 | エステル化合物、その用途およびその製造中間体 |
EP2289889A1 (de) | 2009-08-18 | 2011-03-02 | Endura S.p.a. | Substituierte Alkynylphenoxy-Verbindungen und ihre Verwendungen |
GB201104156D0 (en) | 2011-03-11 | 2011-04-27 | Rothamstead Res Ltd | Compositions and methods for controlling pesticide resistant pests |
GB2512112B (en) * | 2013-03-21 | 2016-03-30 | Rothamsted Res Ltd | Compositions and methods for controlling herbicide resistant weeds |
CN103222473A (zh) * | 2013-05-06 | 2013-07-31 | 南通金陵农化有限公司 | 一种吡虫啉与噻嗪酮复配杀虫剂 |
CN106305732B (zh) * | 2015-06-18 | 2019-03-19 | 沈阳中化农药化工研发有限公司 | 一种含有氟螨嗪的杀虫杀螨组合物 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1239695B (de) * | 1964-12-24 | 1967-05-03 | Bayer Ag | Verfahren zur Herstellung von Phosphor-, Phosphon-, Thionophosphor- oder Thiono-phosphonsaeureestern |
US3402179A (en) * | 1965-01-25 | 1968-09-17 | Sumitomo Chemical Co | Phthalimidomethyl alkynyl ethers |
CH526258A (de) * | 1970-03-25 | 1972-08-15 | Hoffmann La Roche | Schädlingsbekämpfungsmittel |
US3954793A (en) * | 1971-07-20 | 1976-05-04 | Hennessy Douglas J | 1-(2-Propynyl)-1 H-indazole compounds |
US3880999A (en) * | 1971-07-20 | 1975-04-29 | Douglas J Hennessy | Synergistic insecticidal compositions containing benzyl 2-propynyl ethers |
JPS6118744A (ja) * | 1984-07-06 | 1986-01-27 | Kureha Chem Ind Co Ltd | 置換フエニル酢酸エステル誘導体 |
-
1995
- 1995-11-21 HU HU9503318A patent/HU220697B1/hu not_active IP Right Cessation
-
1996
- 1996-11-18 HR HR960545A patent/HRP960545B1/xx not_active IP Right Cessation
- 1996-11-19 EE EE9800140A patent/EE9800140A/xx unknown
- 1996-11-19 DK DK96940053T patent/DK0862545T3/da active
- 1996-11-19 BR BR9611643-9A patent/BR9611643A/pt not_active Application Discontinuation
- 1996-11-19 WO PCT/HU1996/000069 patent/WO1997019040A2/en not_active Application Discontinuation
- 1996-11-19 EA EA199800454A patent/EA002064B1/ru not_active IP Right Cessation
- 1996-11-19 DE DE69628580T patent/DE69628580T2/de not_active Expired - Fee Related
- 1996-11-19 CA CA002238186A patent/CA2238186A1/en not_active Abandoned
- 1996-11-19 CN CN96199336A patent/CN1117055C/zh not_active Expired - Fee Related
- 1996-11-19 AU AU77051/96A patent/AU710995C/en not_active Ceased
- 1996-11-19 KR KR10-1998-0703796A patent/KR100439078B1/ko not_active IP Right Cessation
- 1996-11-19 US US09/068,933 patent/US6277867B1/en not_active Expired - Fee Related
- 1996-11-19 EP EP96940053A patent/EP0862545B1/de not_active Expired - Lifetime
- 1996-11-19 ES ES96940053T patent/ES2202488T3/es not_active Expired - Lifetime
- 1996-11-19 SK SK666-98A patent/SK66698A3/sk unknown
- 1996-11-19 SI SI9630627T patent/SI0862545T1/xx unknown
- 1996-11-19 TR TR1998/00901T patent/TR199800901T2/xx unknown
- 1996-11-19 AT AT96940053T patent/ATE242193T1/de not_active IP Right Cessation
- 1996-11-19 IL IL12449096A patent/IL124490A0/xx unknown
- 1996-11-19 PL PL96327011A patent/PL185691B1/pl not_active IP Right Cessation
- 1996-11-19 NZ NZ323003A patent/NZ323003A/xx unknown
- 1996-11-19 UA UA98063225A patent/UA49864C2/uk unknown
- 1996-11-19 PT PT96940053T patent/PT862545E/pt unknown
- 1996-11-19 CZ CZ981545A patent/CZ154598A3/cs unknown
- 1996-11-19 JP JP51952897A patent/JP3487863B2/ja not_active Expired - Fee Related
- 1996-11-20 YU YU61896A patent/YU61896A/sh unknown
- 1996-11-20 ZA ZA969733A patent/ZA969733B/xx unknown
- 1996-11-21 AR ARP960105273A patent/AR004969A1/es active IP Right Grant
-
1998
- 1998-05-15 NO NO19982234A patent/NO311426B1/no unknown
- 1998-05-21 MX MX9804017A patent/MX9804017A/es unknown
- 1998-05-26 BG BG102488A patent/BG64417B1/bg unknown
-
1999
- 1999-06-30 HK HK99102781A patent/HK1017667A1/xx not_active IP Right Cessation
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