JPH02504273A - 殺虫剤ピラゾリン - Google Patents

殺虫剤ピラゾリン

Info

Publication number: JPH02504273A
Authority: JP; Japan
Prior art keywords: alkyl; cfs; melting point; compound according; dihydro
Prior art date: 1987-07-17
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.): Pending

Application number

JP63506321A

Other languages

English (en)

Japanese (ja)

Inventor

ラム，ジヨージ・フイリツプ

Original Assignee

イー・アイ・デユポン・デ・ニモアス・アンド・カンパニー

Priority date (The priority date 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 date listed.)

1987-07-17

Filing date

1988-07-15

Publication date

1990-12-06

1988-07-15 Application filed by イー・アイ・デユポン・デ・ニモアス・アンド・カンパニー filed Critical イー・アイ・デユポン・デ・ニモアス・アンド・カンパニー

1990-12-06 Publication of JPH02504273A publication Critical patent/JPH02504273A/ja

Status Pending legal-status Critical Current

Links

239000002917 insecticide Substances 0.000 title description 11
DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims description 88
-1 C(O)OCH2CH3 Chemical group 0.000 claims description 29
125000000217 alkyl group Chemical group 0.000 claims description 27
229910052736 halogen Inorganic materials 0.000 claims description 24
QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 22
238000000034 method Methods 0.000 claims description 19
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
239000000203 mixture Substances 0.000 claims description 16
229910052799 carbon Inorganic materials 0.000 claims description 14
150000002367 halogens Chemical class 0.000 claims description 14
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
125000001188 haloalkyl group Chemical group 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 12
241000238631 Hexapoda Species 0.000 claims description 11
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
229940095102 methyl benzoate Drugs 0.000 claims description 11
229910052717 sulfur Inorganic materials 0.000 claims description 10
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000004414 alkyl thio group Chemical group 0.000 claims description 6
125000000304 alkynyl group Chemical group 0.000 claims description 6
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 claims description 6
125000000262 haloalkenyl group Chemical group 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
239000000126 substance Substances 0.000 claims description 6
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
125000004438 haloalkoxy group Chemical group 0.000 claims description 5
101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
230000000749 insecticidal effect Effects 0.000 claims description 4
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
125000004995 haloalkylthio group Chemical group 0.000 claims description 3
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 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
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 6
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 3
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
101100516572 Caenorhabditis elegans nhr-8 gene Proteins 0.000 claims 2
125000006237 oxymethylenoxy group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims 1
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims 1
125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
238000002844 melting Methods 0.000 description 96
230000008018 melting Effects 0.000 description 96
229920000728 polyester Polymers 0.000 description 41
229910052739 hydrogen Inorganic materials 0.000 description 17
230000000704 physical effect Effects 0.000 description 14
238000012360 testing method Methods 0.000 description 14
239000001257 hydrogen Substances 0.000 description 13
238000002360 preparation method Methods 0.000 description 13
238000006243 chemical reaction Methods 0.000 description 12
239000003795 chemical substances by application Substances 0.000 description 11
239000000843 powder Substances 0.000 description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
239000007787 solid Substances 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
241000607479 Yersinia pestis Species 0.000 description 7
239000003085 diluting agent Substances 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000004480 active ingredient Substances 0.000 description 6
239000008187 granular material Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
241000256251 Spodoptera frugiperda Species 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
239000004615 ingredient Substances 0.000 description 5
239000000463 material Substances 0.000 description 5
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 5
239000002245 particle Substances 0.000 description 5
239000000575 pesticide Substances 0.000 description 5
239000002689 soil Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
241000209140 Triticum Species 0.000 description 4
235000021307 Triticum Nutrition 0.000 description 4
230000029936 alkylation Effects 0.000 description 4
238000005804 alkylation reaction Methods 0.000 description 4
125000004093 cyano group Chemical group *C#N 0.000 description 4
125000000753 cycloalkyl group Chemical group 0.000 description 4
238000001035 drying Methods 0.000 description 4
239000007788 liquid Substances 0.000 description 4
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 4
239000004033 plastic Substances 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
239000007921 spray Substances 0.000 description 4
238000005507 spraying Methods 0.000 description 4
238000003756 stirring Methods 0.000 description 4
HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 4
OTKCEEWUXHVZQI-UHFFFAOYSA-N 1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=O)CC1=CC=CC=C1 OTKCEEWUXHVZQI-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
241001414662 Macrosteles fascifrons Species 0.000 description 3
241001147398 Ostrinia nubilalis Species 0.000 description 3
229910052770 Uranium Inorganic materials 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
230000000844 anti-bacterial effect Effects 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
239000000417 fungicide Substances 0.000 description 3
238000000227 grinding Methods 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
230000002262 irrigation Effects 0.000 description 3
238000003973 irrigation Methods 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
238000012015 optical character recognition Methods 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
239000000725 suspension Substances 0.000 description 3
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 2
239000005745 Captan Substances 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
229940126062 Compound A Drugs 0.000 description 2
241000489976 Diabrotica undecimpunctata howardi Species 0.000 description 2
241000256244 Heliothis virescens Species 0.000 description 2
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
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 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
241000220317 Rosa Species 0.000 description 2
125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
241000256248 Spodoptera Species 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
230000000895 acaricidal effect Effects 0.000 description 2
239000000642 acaricide Substances 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000000654 additive Substances 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
229960000892 attapulgite Drugs 0.000 description 2
239000003899 bactericide agent Substances 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
229940117949 captan Drugs 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
PFIADAMVCJPXSF-UHFFFAOYSA-N chloroneb Chemical compound COC1=CC(Cl)=C(OC)C=C1Cl PFIADAMVCJPXSF-UHFFFAOYSA-N 0.000 description 2
239000003245 coal Substances 0.000 description 2
WCMMILVIRZAPLE-UHFFFAOYSA-M cyhexatin Chemical compound C1CCCCC1[Sn](C1CCCCC1)(O)C1CCCCC1 WCMMILVIRZAPLE-UHFFFAOYSA-M 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
230000000887 hydrating effect Effects 0.000 description 2
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
210000003127 knee Anatomy 0.000 description 2
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000005645 nematicide Substances 0.000 description 2
229910052625 palygorskite Inorganic materials 0.000 description 2
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
QYMMJNLHFKGANY-UHFFFAOYSA-N profenofos Chemical compound CCCSP(=O)(OCC)OC1=CC=C(Br)C=C1Cl QYMMJNLHFKGANY-UHFFFAOYSA-N 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
229920005552 sodium lignosulfonate Polymers 0.000 description 2
241000894007 species Species 0.000 description 2
125000003107 substituted aryl group Chemical group 0.000 description 2
239000011593 sulfur Chemical group 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
229960002447 thiram Drugs 0.000 description 2
KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 2
238000013519 translation Methods 0.000 description 2
LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 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
CEYWPVCZMDVGLZ-BEPFRFAYSA-N (2r,3r,5z)-5-ethylidene-2-hydroxy-2,3-dimethylhexanedioic acid Chemical compound C\C=C(C(O)=O)\C[C@@H](C)[C@@](C)(O)C(O)=O CEYWPVCZMDVGLZ-BEPFRFAYSA-N 0.000 description 1
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-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
125000006727 (C1-C6) alkenyl group Chemical group 0.000 description 1
AQKJHZKWTDKLJH-UHFFFAOYSA-N (propan-2-ylamino)phosphonic acid Chemical compound CC(C)NP(O)(O)=O AQKJHZKWTDKLJH-UHFFFAOYSA-N 0.000 description 1
CDASTHKGLSHGJZ-ARJAWSKDSA-N (z)-3-hydroxy-n-methylbut-2-enamide Chemical compound CNC(=O)\C=C(\C)O CDASTHKGLSHGJZ-ARJAWSKDSA-N 0.000 description 1
YIKWKLYQRFRGPM-UHFFFAOYSA-N 1-dodecylguanidine acetate Chemical compound CC(O)=O.CCCCCCCCCCCCN=C(N)N YIKWKLYQRFRGPM-UHFFFAOYSA-N 0.000 description 1
QZTWVDCKDWZCLV-UHFFFAOYSA-N 1-isocyanato-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(N=C=O)C=C1 QZTWVDCKDWZCLV-UHFFFAOYSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
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 description 1
WOOHLGIEZWGDAV-UHFFFAOYSA-N 2-hydroxy-1-[4-(hydroxymethyl)phenyl]-2-phenylethanone Chemical compound C1=CC(CO)=CC=C1C(=O)C(O)C1=CC=CC=C1 WOOHLGIEZWGDAV-UHFFFAOYSA-N 0.000 description 1
ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
PPJDSJPSCDUDQR-UHFFFAOYSA-N 3,3,5-triphenyl-1,2-dihydropyrazole Chemical class C1(=CC=CC=C1)C1(C=C(NN1)C1=CC=CC=C1)C1=CC=CC=C1 PPJDSJPSCDUDQR-UHFFFAOYSA-N 0.000 description 1
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 1
FKQBSKWHFPMVNS-UHFFFAOYSA-N 4-chloro-2-(chloromethylidene)-3,3-bis(trichloromethyl)bicyclo[2.2.1]heptane;diethoxy-(6-methyl-2-propan-2-ylpyrimidin-4-yl)oxy-sulfanylidene-$l^{5}-phosphane Chemical compound C1CC2(Cl)C(C(Cl)(Cl)Cl)(C(Cl)(Cl)Cl)C(=CCl)C1C2.CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FKQBSKWHFPMVNS-UHFFFAOYSA-N 0.000 description 1
AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
ZLZQFBHACGTOJG-UHFFFAOYSA-N 4ah-quinoxalin-2-one Chemical compound C1=CC=CC2=NC(=O)C=NC21 ZLZQFBHACGTOJG-UHFFFAOYSA-N 0.000 description 1
DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
PVFOHMXILQEIHX-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-bromophenyl)ethyl]purin-6-amine Chemical compound C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Br PVFOHMXILQEIHX-UHFFFAOYSA-N 0.000 description 1
239000005660 Abamectin Substances 0.000 description 1
241000251468 Actinopterygii Species 0.000 description 1
241000254175 Anthonomus grandis Species 0.000 description 1
241000132092 Aster Species 0.000 description 1
235000005781 Avena Nutrition 0.000 description 1
244000075850 Avena orientalis Species 0.000 description 1
241000193388 Bacillus thuringiensis Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
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RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 description 1
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XAMUDJHXFNRLCY-UHFFFAOYSA-N phenthoate Chemical compound CCOC(=O)C(SP(=S)(OC)OC)C1=CC=CC=C1 XAMUDJHXFNRLCY-UHFFFAOYSA-N 0.000 description 1
LMNZTLDVJIUSHT-UHFFFAOYSA-N phosmet Chemical compound C1=CC=C2C(=O)N(CSP(=S)(OC)OC)C(=O)C2=C1 LMNZTLDVJIUSHT-UHFFFAOYSA-N 0.000 description 1
235000003270 potassium fluoride Nutrition 0.000 description 1
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OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
229910052939 potassium sulfate Inorganic materials 0.000 description 1
235000011151 potassium sulphates Nutrition 0.000 description 1
239000011814 protection agent Substances 0.000 description 1
150000003219 pyrazolines Chemical class 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
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239000008247 solid mixture Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
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239000004575 stone Substances 0.000 description 1
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239000003826 tablet Substances 0.000 description 1
238000010998 test method Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-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
OEJNXTAZZBRGDN-UHFFFAOYSA-N toxaphene Chemical compound ClC1C(Cl)C2(Cl)C(CCl)(CCl)C(=C)C1(Cl)C2(Cl)Cl OEJNXTAZZBRGDN-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
229940035339 tri-chlor Drugs 0.000 description 1
KMBOMSSFAQSGQY-UHFFFAOYSA-N trimethyl(2-phenylmethoxyethyl)azanium Chemical compound C[N+](C)(C)CCOCC1=CC=CC=C1 KMBOMSSFAQSGQY-UHFFFAOYSA-N 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
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1
238000010792 warming Methods 0.000 description 1
239000002023 wood Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- 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
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (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)

JP63506321A 1987-07-17 1988-07-15 殺虫剤ピラゾリン Pending JPH02504273A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US7479587A	1987-07-17	1987-07-17
US074,795		1987-07-17

Publications (1)

Publication Number	Publication Date
JPH02504273A true JPH02504273A (ja)	1990-12-06

Family

ID=22121740

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP63506321A Pending JPH02504273A (ja)	1987-07-17	1988-07-15	殺虫剤ピラゾリン

Country Status (4)

Country	Link
EP (1)	EP0367796A1 (fr)
JP (1)	JPH02504273A (fr)
AU (1)	AU1993988A (fr)
WO (1)	WO1989000562A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2008110971A (ja) *	2006-10-06	2008-05-15	Nippon Soda Co Ltd	含窒素複素環化合物および有害生物防除剤
JP2008133273A (ja) *	2006-11-01	2008-06-12	Nippon Soda Co Ltd	含窒素へテロ環化合物および有害生物防除剤

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU7884691A (en) *	1990-05-15	1991-12-10	E.I. Du Pont De Nemours And Company	Arthropodicidal tetrahydropyridazines
WO2010093595A1 (fr)	2009-02-10	2010-08-19	E. I. Du Pont De Nemours And Company	2‑pyridones fongicides

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL158178B (nl) *	1974-07-12	1978-10-16	Philips Nv	Werkwijze ter bereiding van insekticide preparaten die een pyrazolinederivaat bevatten, aldus verkregen gevormde preparaten, en werkwijze ter bereiding van pyrazolinederivaten met insekticide werking.
DE3064749D1 (en) *	1979-07-03	1983-10-13	Duphar Int Res	New pyrazoline derivatives, method of preparing the new compounds, as well as insecticidal composition on the basis of these new compounds
US4663341A (en) *	1984-02-16	1987-05-05	Rohm And Haas Company	Insecticidal n-aryl-3-aryl-4,5-dihydro-1h-pyrazole-1-carboxamides
AU556949B2 (en) *	1984-10-25	1986-11-27	Fmc Corporation	Pyrozoline insecticides

1988
- 1988-07-15 EP EP19880906671 patent/EP0367796A1/fr active Pending
- 1988-07-15 JP JP63506321A patent/JPH02504273A/ja active Pending
- 1988-07-15 WO PCT/US1988/002335 patent/WO1989000562A1/fr not_active Ceased
- 1988-07-15 AU AU19939/88A patent/AU1993988A/en not_active Abandoned

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2008110971A (ja) *	2006-10-06	2008-05-15	Nippon Soda Co Ltd	含窒素複素環化合物および有害生物防除剤
JP2008133273A (ja) *	2006-11-01	2008-06-12	Nippon Soda Co Ltd	含窒素へテロ環化合物および有害生物防除剤

Also Published As

Publication number	Publication date
WO1989000562A1 (fr)	1989-01-26
EP0367796A1 (fr)	1990-05-16
AU1993988A (en)	1989-02-13

Publication	Publication Date	Title
JPH0581591B2 (fr)	1993-11-15
DE69524925T2 (de)	2002-08-22	Pyrazinone und ihre Verwendung als Fungizide
TW362952B (en)	1999-07-01	Arylpyrazole insecticides
JPH06504777A (ja)	1994-06-02	殺節足動物性カルボキシアニリド類
JP3728324B2 (ja)	2005-12-21	１−置換−４−カルバモイル−１，２，４−トリアゾール−５−オン誘導体及び除草剤
JPH06502414A (ja)	1994-03-17	セミカルバゾン殺節足動物剤
JPH08157312A (ja)	1996-06-18	水稲用除草剤
JPH02502906A (ja)	1990-09-13	殺虫性置換インダゾール類
JPH01275572A (ja)	1989-11-06	置換されたトリアゾール
US5164396A (en)	1992-11-17	Barbituric acid derivatives having insecticidal activity
JPS63190880A (ja)	1988-08-08	新規ｎ−ベンゾチアゾリル−アミド類及び殺虫剤
JPH0291062A (ja)	1990-03-30	トリアゾール誘導体及び殺虫剤
JPH05507087A (ja)	1993-10-14	殺節足動物性テトラヒドロピリダジン類
JP2905982B2 (ja)	1999-06-14	複素環含有フェニルピラゾール誘導体又はその塩類及びその製造方法並びに除草剤
JPH07285962A (ja)	1995-10-31	ピリジンカルボン酸アミド誘導体
CS205149B2 (en)	1981-04-30	Herbicide,insecticide,fungicide or nematocide means and method of making the active substance
EP0300692A1 (fr)	1989-01-25	Pyrazolines insecticides
JP2002520384A (ja)	2002-07-09	アリールビニルエーテル誘導体およびそれらの除草剤としての使用
JPS6326757B2 (fr)	1988-05-31
CS252497B2 (en)	1987-09-17	Insecticide and method of efficient substances production
JPS6365069B2 (fr)	1988-12-14
JPH04500810A (ja)	1992-02-13	Ｎ―スルフエニル化、及びｎ―アシル化ピラゾリン
JPH04235975A (ja)	1992-08-25	ピリダジノン誘導体および害虫防除剤
JPS6314711B2 (fr)	1988-04-01
US5006524A (en)	1991-04-09	Triphenyl pyrazoline compounds which are useful as insecticides

JPH02504273A - 殺虫剤ピラゾリン - Google Patents

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