KR20050049512A - 안트라닐아미드 살충제 - Google Patents
안트라닐아미드 살충제 Download PDFInfo
- Publication number
- KR20050049512A KR20050049512A KR1020057005681A KR20057005681A KR20050049512A KR 20050049512 A KR20050049512 A KR 20050049512A KR 1020057005681 A KR1020057005681 A KR 1020057005681A KR 20057005681 A KR20057005681 A KR 20057005681A KR 20050049512 A KR20050049512 A KR 20050049512A
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- alkyl
- independently
- halogen
- alkoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
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- 239000002917 insecticide Substances 0.000 title description 6
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical compound NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 title 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 151
- 239000000203 mixture Substances 0.000 claims abstract description 92
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 69
- 238000000034 method Methods 0.000 claims abstract description 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 25
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 18
- 239000003085 diluting agent Substances 0.000 claims abstract description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 239000007787 solid Substances 0.000 claims abstract description 10
- 239000004094 surface-active agent Substances 0.000 claims abstract description 10
- 239000007788 liquid Substances 0.000 claims abstract description 8
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
- -1 C 1 -C 4 alkoxy Chemical group 0.000 claims description 62
- 125000001424 substituent group Chemical group 0.000 claims description 29
- 229910052799 carbon Inorganic materials 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 27
- 150000002367 halogens Chemical class 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 17
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 15
- 239000013543 active substance Substances 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 239000007921 spray Substances 0.000 claims description 14
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 12
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 11
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 10
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 10
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims description 10
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 7
- 235000013305 food Nutrition 0.000 claims description 7
- 241000239290 Araneae Species 0.000 claims description 6
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- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
- 239000005667 attractant Substances 0.000 claims description 6
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- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 4
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- 125000003545 alkoxy group Chemical group 0.000 claims description 4
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- 241001494115 Stomoxys calcitrans Species 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 230000031902 chemoattractant activity Effects 0.000 claims description 3
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 3
- 239000003906 humectant Substances 0.000 claims description 3
- 239000007924 injection Substances 0.000 claims description 3
- 238000002347 injection Methods 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 241000392928 Parachromis friedrichsthalii Species 0.000 claims 1
- 210000003056 antler Anatomy 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 25
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 23
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 19
- 238000003786 synthesis reaction Methods 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000002253 acid Substances 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- 238000012360 testing method Methods 0.000 description 17
- 230000015572 biosynthetic process Effects 0.000 description 16
- 241000196324 Embryophyta Species 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 241001124076 Aphididae Species 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000009472 formulation Methods 0.000 description 13
- 241000238631 Hexapoda Species 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 239000008187 granular material Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- 125000001188 haloalkyl group Chemical group 0.000 description 9
- HQQTZCPKNZVLFF-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one Chemical compound C1=CC=C2ONC(=O)CC2=C1 HQQTZCPKNZVLFF-UHFFFAOYSA-N 0.000 description 8
- 241000244206 Nematoda Species 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 240000008042 Zea mays Species 0.000 description 8
- 229940125904 compound 1 Drugs 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 7
- 241000721621 Myzus persicae Species 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 7
- 230000006378 damage Effects 0.000 description 7
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 7
- 230000003647 oxidation Effects 0.000 description 7
- 238000007254 oxidation reaction Methods 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 239000002002 slurry Substances 0.000 description 7
- 239000002689 soil Substances 0.000 description 7
- 238000005507 spraying Methods 0.000 description 7
- 241000238876 Acari Species 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 241000258937 Hemiptera Species 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 6
- 235000005822 corn Nutrition 0.000 description 6
- 235000013399 edible fruits Nutrition 0.000 description 6
- VYFOAVADNIHPTR-UHFFFAOYSA-N isatoic anhydride Chemical compound NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 5
- 239000005660 Abamectin Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
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- 229920000742 Cotton Polymers 0.000 description 5
- 241000257303 Hymenoptera Species 0.000 description 5
- 241000500437 Plutella xylostella Species 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 239000008188 pellet Substances 0.000 description 5
- 239000000575 pesticide Substances 0.000 description 5
- 150000003217 pyrazoles Chemical group 0.000 description 5
- 150000003512 tertiary amines Chemical class 0.000 description 5
- 241000962514 Alosa chrysochloris Species 0.000 description 4
- 241000273311 Aphis spiraecola Species 0.000 description 4
- 241000193388 Bacillus thuringiensis Species 0.000 description 4
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- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 4
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
- 241000721451 Pectinophora gossypiella Species 0.000 description 4
- 241001516577 Phylloxera Species 0.000 description 4
- 240000003768 Solanum lycopersicum Species 0.000 description 4
- 235000002595 Solanum tuberosum Nutrition 0.000 description 4
- 244000061456 Solanum tuberosum Species 0.000 description 4
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- 241000255993 Trichoplusia ni Species 0.000 description 4
- 229940097012 bacillus thuringiensis Drugs 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 239000004495 emulsifiable concentrate Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000000417 fungicide Substances 0.000 description 4
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- 125000004356 hydroxy functional group Chemical group O* 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
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- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
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- 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 3
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- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229940080817 rotenone Drugs 0.000 description 1
- JUVIOZPCNVVQFO-UHFFFAOYSA-N rotenone Natural products O1C2=C3CC(C(C)=C)OC3=CC=C2C(=O)C2C1COC1=C2C=C(OC)C(OC)=C1 JUVIOZPCNVVQFO-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000003195 sodium channel blocking agent Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- JNYAEWCLZODPBN-CTQIIAAMSA-N sorbitan Polymers OCC(O)C1OCC(O)[C@@H]1O JNYAEWCLZODPBN-CTQIIAAMSA-N 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- PUYXTUJWRLOUCW-UHFFFAOYSA-N spiroxamine Chemical compound O1C(CN(CC)CCC)COC11CCC(C(C)(C)C)CC1 PUYXTUJWRLOUCW-UHFFFAOYSA-N 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000004548 suspo-emulsion Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 239000005936 tau-Fluvalinate Substances 0.000 description 1
- INISTDXBRIBGOC-XMMISQBUSA-N tau-fluvalinate Chemical compound N([C@H](C(C)C)C(=O)OC(C#N)C=1C=C(OC=2C=CC=CC=2)C=CC=1)C1=CC=C(C(F)(F)F)C=C1Cl INISTDXBRIBGOC-XMMISQBUSA-N 0.000 description 1
- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 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
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- LITQZINTSYBKIU-UHFFFAOYSA-F tetracopper;hexahydroxide;sulfate Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Cu+2].[Cu+2].[Cu+2].[Cu+2].[O-]S([O-])(=O)=O LITQZINTSYBKIU-UHFFFAOYSA-F 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- 229960004546 thiabendazole Drugs 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
- 239000002562 thickening agent Substances 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
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- 239000002383 tung oil Substances 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
Classifications
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
-
- 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41636402P | 2002-10-04 | 2002-10-04 | |
| US60/416,364 | 2002-10-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20050049512A true KR20050049512A (ko) | 2005-05-25 |
Family
ID=32093852
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020057005681A Withdrawn KR20050049512A (ko) | 2002-10-04 | 2003-10-01 | 안트라닐아미드 살충제 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7211270B2 (https=) |
| EP (1) | EP1546160A1 (https=) |
| JP (1) | JP2006502226A (https=) |
| KR (1) | KR20050049512A (https=) |
| CN (1) | CN100349901C (https=) |
| AU (1) | AU2003282711A1 (https=) |
| BR (1) | BR0314497A (https=) |
| MX (1) | MXPA05003337A (https=) |
| WO (1) | WO2004033468A1 (https=) |
Families Citing this family (66)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR036872A1 (es) | 2001-08-13 | 2004-10-13 | Du Pont | Compuesto de antranilamida, composicion que lo comprende y metodo para controlar una plaga de invertebrados |
| EP1423379B1 (en) | 2001-08-15 | 2008-05-28 | E.I. du Pont de Nemours and Company | Ortho-substituted aryl amides for controlling invertebrate pests |
| ES2319743T3 (es) | 2001-08-16 | 2009-05-12 | E.I. Du Pont De Nemours And Company | Antranilamidas sustituidas para controlar plagas de invertebrados. |
| WO2004046129A2 (en) * | 2002-11-15 | 2004-06-03 | E.I. Du Pont De Nemours And Company | Novel anthranilamide insecticides |
| SI1599463T1 (sl) * | 2003-01-28 | 2013-10-30 | E.I. Du Pont De Nemours And Company | Ciano antranilamidni insekticidi |
| KR20060008336A (ko) | 2003-06-12 | 2006-01-26 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 융합된 옥사지논 제조 방법 |
| RU2006139953A (ru) * | 2004-04-13 | 2008-05-20 | Е.И. Дюпон Де Немур Энд Компани (Us) | Антраниламидные инсектициды |
| ES2413442T3 (es) * | 2004-11-18 | 2013-07-16 | E. I. Du Pont De Nemours And Company | Insecticidas de antranilamida |
| TWI363756B (en) * | 2004-12-07 | 2012-05-11 | Du Pont | Method for preparing n-phenylpyrazole-1-carboxamides |
| GB0427008D0 (en) * | 2004-12-09 | 2005-01-12 | Syngenta Participations Ag | Novel insecticides |
| US8143292B2 (en) | 2005-07-07 | 2012-03-27 | Basf Se | N-Thio-anthranilamid compounds and their use as pesticides |
| GB0516703D0 (en) * | 2005-08-15 | 2005-09-21 | Syngenta Participations Ag | Novel insecticides |
| AU2006283181A1 (en) * | 2005-08-24 | 2007-03-01 | E. I. Du Pont De Nemours And Company | Anthranilamides for controlling invertebrate pests |
| DE102005044108A1 (de) | 2005-09-15 | 2007-03-29 | Bayer Cropscience Ag | Dioxazin- und Oxdiazin-substituierte Arylamide |
| AR059035A1 (es) | 2006-01-16 | 2008-03-12 | Syngenta Participations Ag | Insecticidas derivados de antranilamida |
| CN101466702B (zh) * | 2006-06-13 | 2014-04-02 | 拜尔农作物科学股份公司 | 具有杂芳族和杂环族取代基的邻氨基苯甲酰二胺衍生物 |
| DE102006032168A1 (de) | 2006-06-13 | 2007-12-20 | Bayer Cropscience Ag | Anthranilsäurediamid-Derivate mit heteroaromatischen Substituenten |
| JP5424874B2 (ja) | 2006-06-22 | 2014-02-26 | ビーエーエスエフ ソシエタス・ヨーロピア | マロノニトリル化合物 |
| CN101534650B (zh) | 2006-09-14 | 2014-06-11 | 巴斯夫欧洲公司 | 杀虫剂组合物 |
| WO2008034787A2 (en) | 2006-09-18 | 2008-03-27 | Basf Se | Pesticidal mixtures comprising an anthranilamide insecticide and a fungicide |
| WO2008055208A1 (en) * | 2006-11-01 | 2008-05-08 | New Jersey Institute Of Technology | Aerogel-based filtration of gas phase systems |
| UA110598C2 (uk) | 2006-11-10 | 2016-01-25 | Басф Се | Спосіб одержання кристалічної модифікації фіпронілу |
| US8791046B2 (en) | 2006-11-10 | 2014-07-29 | Basf Se | Crystalline modification of fipronil |
| BRPI0718717A2 (pt) | 2006-11-10 | 2013-11-26 | Basf Se | Modificação cristalina ii de fipronil, fipronil sólido, processo para preparar a modificação cristalina ii, mistura pesticida ou parasiticida sinergística, composição pesticida ou parasiticida, uso da modificação cristalina ii, ou do fipronil sólido, ou da mistura, ou da composição, métodos para controlar pragas, para proteger uma planta da infestação e ataque por pragas, para proteger semente, e para tratar, controlar, prevenir ou proteger animais contra infestação ou infecção por parasitas, semente, uso da modificação cristalina ii, ou do fipronil sólido, ou da mistura, ou da composição, e, processo para a preparação de uma composição para trtar, controlar, prevenir ou proteger animais contra infestação ou infecção por parasitas |
| JP5931322B2 (ja) | 2006-11-10 | 2016-06-08 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | フィプロニルの結晶変態 |
| EA200900654A1 (ru) | 2006-11-30 | 2009-12-30 | Басф Се | Агрохимические композиции, содержащие сополимеры 1-винил-2-пирролидинона |
| CA2668564A1 (en) | 2006-11-30 | 2008-06-05 | Basf Se | Agrochemical formulations comprising n-vinylamid co-polymers |
| DE602007008754D1 (de) | 2006-11-30 | 2010-10-07 | Basf Se | Landwirtschaftliche formulierungen mit copolymeren auf basis von diisocyanaten |
| EP2164323A1 (en) | 2006-12-15 | 2010-03-24 | Rohm and Haas Company | Mixtures comprising 1-methylcyclopropene |
| CN104206402B (zh) | 2007-04-12 | 2018-04-24 | 巴斯夫欧洲公司 | 包含氰基亚磺酰亚胺基化合物的农药混合物 |
| CA2682294A1 (en) | 2007-04-23 | 2008-10-30 | Basf Se | Plant productivity enhancement by combining chemical agents with transgenic modifications |
| WO2008134970A1 (fr) * | 2007-04-30 | 2008-11-13 | Sinochem Corporation | Composés anthranilamides et leur utilisation |
| MX2010001666A (es) | 2007-08-16 | 2010-03-10 | Basf Se | Composiciones y metodos para el tratamiento de semillas. |
| EP2500340A1 (en) | 2008-01-25 | 2012-09-19 | Syngenta Participations AG. | 2-Cyanophenyl Sulfonamide Derivatives Useful as Pesticides |
| CN101550130B (zh) * | 2008-04-01 | 2012-11-07 | 中国中化股份有限公司 | 一种制备3-卤代-1-(3-氯-2-吡啶基)-1h-吡唑-5-甲酰卤的方法 |
| US20090318393A1 (en) * | 2008-06-23 | 2009-12-24 | Shalaby Shalaby W | Film-forming liquid formulations for controlled release of pesticides |
| CA2747035C (en) | 2008-12-18 | 2017-01-24 | Bayer Cropscience Ag | Tetrazole substituted anthranilic acid amides as pesticides |
| EP2533641B1 (de) | 2010-02-09 | 2016-07-13 | Bayer CropScience AG | Hydrazin-substituierte anthranilsäurederivate |
| BR112012026523B1 (pt) | 2010-04-16 | 2018-11-27 | Bayer Intellectual Property Gmbh | antranilamidas substituídas com triazol, composições agroquímicas para controlar insetos prejudiciais e composições para controlar insetos prejudiciais as compreendendo, seu processo para preparar composições agroquímicas e uso, bem como método para controlar pragas animais ou fungos fitopatogênicos |
| KR20130089232A (ko) | 2010-06-15 | 2013-08-09 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | 안트라닐산 디아미드 유도체 |
| ES2554903T3 (es) | 2010-06-15 | 2015-12-28 | Bayer Intellectual Property Gmbh | Derivados de diamida de ácido antranílico con cadenas laterales cíclicas |
| KR20130087495A (ko) | 2010-06-15 | 2013-08-06 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | 안트라닐산 유도체 |
| JP6025717B2 (ja) | 2010-06-15 | 2016-11-16 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 新規なオルト置換されたアリールアミド誘導体 |
| ES2555264T3 (es) | 2010-07-09 | 2015-12-30 | Bayer Intellectual Property Gmbh | Derivados de antranilamida como pesticidas |
| KR20140006007A (ko) * | 2011-01-28 | 2014-01-15 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 2-아미노벤즈아미드 유도체의 제조 방법 |
| JP2014529587A (ja) * | 2011-08-12 | 2014-11-13 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | Ｎ−チオ−アントラニルアミド化合物、及び殺有害生物剤としてのそれらの使用 |
| ES2558166T3 (es) | 2011-08-12 | 2016-02-02 | Basf Se | Compuestos de N-tio-antranilamida y su uso como pesticidas |
| EP2606732A1 (en) | 2011-12-19 | 2013-06-26 | Bayer CropScience AG | Use of an anthranilic diamide derivatives with heteroaromatic and heterocyclic substituents in combination with a biological control agent |
| US9414595B2 (en) | 2011-12-19 | 2016-08-16 | Bayer Cropscience Ag | Use of anthranilic acid diamide derivatives for pest control in transgenic crops |
| CA2873266A1 (en) | 2012-05-24 | 2013-11-28 | Basf Se | N-thio-anthranilamide compounds and their use as pesticides |
| EP2964629A1 (de) | 2013-03-06 | 2016-01-13 | Bayer CropScience Aktiengesellschaft | Alkoximino substituierte anthranilsäurediamide als pestizide |
| CA2925953C (en) | 2013-10-17 | 2021-11-02 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
| CN103880749B (zh) * | 2014-02-26 | 2019-01-01 | 南通大学 | 一种3-甲基-5-吡唑甲酸甲酯的化学合成方法 |
| JP2017525703A (ja) * | 2014-08-19 | 2017-09-07 | ダウ アグロサイエンシィズ エルエルシー | ３−（３−クロロ−１ｈ−ピラゾール−１−イル）ピリジンの調製方法 |
| PL3377486T3 (pl) | 2015-11-18 | 2025-02-24 | Monsanto Technology Llc | Sposób zwalczania szkodników owadzich |
| CN106928183B (zh) * | 2015-12-29 | 2019-09-24 | 沈阳中化农药化工研发有限公司 | 吡啶基吡唑烷酮羧酸类化合物的制备方法 |
| CN110325036B (zh) | 2016-12-29 | 2021-10-26 | 美国陶氏益农公司 | 用于制备杀虫化合物的方法 |
| EP3728256B1 (en) | 2017-12-20 | 2024-10-02 | PI Industries Ltd. | Pyrazolopyridine-diamides, their use as insecticide and processes for preparing the same |
| WO2019123194A1 (en) | 2017-12-20 | 2019-06-27 | Pi Industries Ltd. | Anthranilamides, their use as insecticide and processes for preparing the same. |
| WO2019150220A1 (en) | 2018-01-30 | 2019-08-08 | Pi Industries Ltd. | Novel anthranilamides, their use as insecticide and processes for preparing the same. |
| EA202191554A1 (ru) | 2018-12-03 | 2021-09-02 | Фмк Корпорейшн | Способ получения n-фенилпиразол-1-карбоксамидов |
| CN111072630A (zh) * | 2019-12-13 | 2020-04-28 | 东南大学 | 一种溴代吡唑类化合物中间体的制备方法与应用 |
| US20240308988A1 (en) | 2021-08-05 | 2024-09-19 | Syngenta Crop Protection Ag | Method For Controlling Diamide Resistant Pests and Compounds Therefor |
| WO2023110710A1 (en) | 2021-12-13 | 2023-06-22 | Syngenta Crop Protection Ag | Method for controlling diamide resistant pests & compounds therefor |
| WO2024133426A1 (en) | 2022-12-21 | 2024-06-27 | Syngenta Crop Protection Ag | Method for controlling diamide resistant pests and compounds therefor |
| WO2025242701A1 (en) | 2024-05-22 | 2025-11-27 | Basf Se | Seed treatment compositions |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY138097A (en) * | 2000-03-22 | 2009-04-30 | Du Pont | Insecticidal anthranilamides |
| IL157046A0 (en) * | 2001-02-06 | 2004-02-08 | Bayer Cropscience Ag | Phthalic acid diamide, method for the production thereof and the use of the same as a pesticide |
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2003
- 2003-10-01 CN CNB2003801008458A patent/CN100349901C/zh not_active Expired - Fee Related
- 2003-10-01 KR KR1020057005681A patent/KR20050049512A/ko not_active Withdrawn
- 2003-10-01 BR BR0314497-6A patent/BR0314497A/pt not_active IP Right Cessation
- 2003-10-01 EP EP03774596A patent/EP1546160A1/en not_active Withdrawn
- 2003-10-01 AU AU2003282711A patent/AU2003282711A1/en not_active Abandoned
- 2003-10-01 WO PCT/US2003/031677 patent/WO2004033468A1/en not_active Ceased
- 2003-10-01 MX MXPA05003337A patent/MXPA05003337A/es not_active Application Discontinuation
- 2003-10-01 US US10/527,863 patent/US7211270B2/en not_active Expired - Fee Related
- 2003-10-01 JP JP2004543434A patent/JP2006502226A/ja not_active Withdrawn
Also Published As
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|---|---|
| JP2006502226A (ja) | 2006-01-19 |
| AU2003282711A1 (en) | 2004-05-04 |
| CN1703417A (zh) | 2005-11-30 |
| EP1546160A1 (en) | 2005-06-29 |
| CN100349901C (zh) | 2007-11-21 |
| BR0314497A (pt) | 2005-08-02 |
| US7211270B2 (en) | 2007-05-01 |
| MXPA05003337A (es) | 2005-07-05 |
| US20060052343A1 (en) | 2006-03-09 |
| WO2004033468A1 (en) | 2004-04-22 |
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