TWI410405B - 酯化合物與其用途 - Google Patents
酯化合物與其用途 Download PDFInfo
- Publication number
- TWI410405B TWI410405B TW097105304A TW97105304A TWI410405B TW I410405 B TWI410405 B TW I410405B TW 097105304 A TW097105304 A TW 097105304A TW 97105304 A TW97105304 A TW 97105304A TW I410405 B TWI410405 B TW I410405B
- Authority
- TW
- Taiwan
- Prior art keywords
- configuration
- cyclopropane ring
- substituent
- compound
- formula
- Prior art date
Links
- -1 Ester compound Chemical class 0.000 title claims abstract description 38
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 44
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 29
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 29
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 29
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 18
- 239000004480 active ingredient Substances 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims description 21
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 193
- 150000001875 compounds Chemical class 0.000 description 163
- 125000001424 substituent group Chemical group 0.000 description 141
- 239000000203 mixture Substances 0.000 description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 23
- 239000000243 solution Substances 0.000 description 21
- 238000009472 formulation Methods 0.000 description 18
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 239000000843 powder Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 239000002917 insecticide Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000004927 clay Substances 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 239000003350 kerosene Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000443 aerosol Substances 0.000 description 6
- 239000002316 fumigant Substances 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical group CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 5
- 229910000420 cerium oxide Inorganic materials 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 241001609607 Delia platura Species 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000000440 bentonite Substances 0.000 description 4
- 229910000278 bentonite Inorganic materials 0.000 description 4
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 235000013312 flour Nutrition 0.000 description 4
- 239000003915 liquefied petroleum gas Substances 0.000 description 4
- 239000002562 thickening agent Substances 0.000 description 4
- GNPWYHFXSMINJQ-UHFFFAOYSA-N 1,2-dimethyl-3-(1-phenylethyl)benzene Chemical compound C=1C=CC(C)=C(C)C=1C(C)C1=CC=CC=C1 GNPWYHFXSMINJQ-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000238662 Blatta orientalis Species 0.000 description 3
- 240000007124 Brassica oleracea Species 0.000 description 3
- 241000254173 Coleoptera Species 0.000 description 3
- 241000254171 Curculionidae Species 0.000 description 3
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 241000255925 Diptera Species 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 241000238631 Hexapoda Species 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000257159 Musca domestica Species 0.000 description 3
- 241000358422 Nephotettix cincticeps Species 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 241000488583 Panonychus ulmi Species 0.000 description 3
- 241001510001 Periplaneta brunnea Species 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 241000254113 Tribolium castaneum Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000000919 ceramic Substances 0.000 description 3
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000000796 flavoring agent Substances 0.000 description 3
- 235000019634 flavors Nutrition 0.000 description 3
- 230000009969 flowable effect Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000003094 microcapsule Substances 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 239000002023 wood Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- 241000254032 Acrididae Species 0.000 description 2
- 241001553884 Aleuroglyphus ovatus Species 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 241000519879 Anomala cuprea Species 0.000 description 2
- 241001124076 Aphididae Species 0.000 description 2
- 241000238657 Blattella germanica Species 0.000 description 2
- 241001674044 Blattodea Species 0.000 description 2
- 241000318995 Bostrichidae Species 0.000 description 2
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 2
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 2
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241001124134 Chrysomelidae Species 0.000 description 2
- 241001498622 Cixius wagneri Species 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 241000489976 Diabrotica undecimpunctata howardi Species 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 241000953886 Fannia canicularis Species 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- 241000258937 Hemiptera Species 0.000 description 2
- 241000257303 Hymenoptera Species 0.000 description 2
- 241001470017 Laodelphax striatella Species 0.000 description 2
- 241000966204 Lissorhoptrus oryzophilus Species 0.000 description 2
- 241000406668 Loxodonta cyclotis Species 0.000 description 2
- 241000257226 Muscidae Species 0.000 description 2
- 241000581981 Muscina stabulans Species 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- 241001556089 Nilaparvata lugens Species 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 241001622642 Parnara bada Species 0.000 description 2
- 241000517306 Pediculus humanus corporis Species 0.000 description 2
- 241000238675 Periplaneta americana Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000437063 Phyllotreta striolata Species 0.000 description 2
- 241000500437 Plutella xylostella Species 0.000 description 2
- 241000254154 Sitophilus zeamais Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 241000176086 Sogatella furcifera Species 0.000 description 2
- 240000004460 Tanacetum coccineum Species 0.000 description 2
- 241000254109 Tenebrio molitor Species 0.000 description 2
- 241000254107 Tenebrionidae Species 0.000 description 2
- 241000255588 Tephritidae Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 241001454295 Tetranychidae Species 0.000 description 2
- 241000488589 Tetranychus kanzawai Species 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- ROVGZAWFACYCSP-MQBLHHJJSA-N [2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-MQBLHHJJSA-N 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 235000010980 cellulose Nutrition 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 235000012343 cottonseed oil Nutrition 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 239000000077 insect repellent Substances 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- HCZKYJDFEPMADG-TXEJJXNPSA-N masoprocol Chemical compound C([C@H](C)[C@H](C)CC=1C=C(O)C(O)=CC=1)C1=CC=C(O)C(O)=C1 HCZKYJDFEPMADG-TXEJJXNPSA-N 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- 229940015367 pyrethrum Drugs 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- 239000000230 xanthan gum Substances 0.000 description 2
- 229920001285 xanthan gum Polymers 0.000 description 2
- 235000010493 xanthan gum Nutrition 0.000 description 2
- 229940082509 xanthan gum Drugs 0.000 description 2
- ZCVAOQKBXKSDMS-AQYZNVCMSA-N (+)-trans-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-AQYZNVCMSA-N 0.000 description 1
- XLOPRKKSAJMMEW-SFYZADRCSA-N (+)-trans-chrysanthemic acid Chemical compound CC(C)=C[C@@H]1[C@@H](C(O)=O)C1(C)C XLOPRKKSAJMMEW-SFYZADRCSA-N 0.000 description 1
- CXBMCYHAMVGWJQ-CABCVRRESA-N (1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)methyl (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCN1C(=O)C(CCCC2)=C2C1=O CXBMCYHAMVGWJQ-CABCVRRESA-N 0.000 description 1
- CAHDYBILHOVOSN-JGVFFNPUSA-N (1S,3S)-3-(2-cyanoprop-1-enyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC(=C[C@H]1[C@H](C(O)=O)C1(C)C)C#N CAHDYBILHOVOSN-JGVFFNPUSA-N 0.000 description 1
- CAHDYBILHOVOSN-SFYZADRCSA-N (1r,3r)-3-(2-cyanoprop-1-enyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound N#CC(C)=C[C@@H]1[C@@H](C(O)=O)C1(C)C CAHDYBILHOVOSN-SFYZADRCSA-N 0.000 description 1
- AHVKNBRJVKCGKJ-IBCQBUCCSA-N (1r,3r,4r,6s)-4,7,7-trimethylbicyclo[4.1.0]heptane-3,4-diol Chemical compound C1[C@@H](O)[C@](C)(O)C[C@@H]2C(C)(C)[C@@H]21 AHVKNBRJVKCGKJ-IBCQBUCCSA-N 0.000 description 1
- GJEGXOUIWJIPTB-UHFFFAOYSA-N (2,3,5,6-tetrafluoro-4-methoxyphenyl)methanol Chemical compound COC1=C(F)C(F)=C(CO)C(F)=C1F GJEGXOUIWJIPTB-UHFFFAOYSA-N 0.000 description 1
- PJCSTULKVNHEGW-UHFFFAOYSA-N (2,3,5,6-tetrafluoro-4-methylphenyl)methanol Chemical compound CC1=C(F)C(F)=C(CO)C(F)=C1F PJCSTULKVNHEGW-UHFFFAOYSA-N 0.000 description 1
- WCXDHFDTOYPNIE-RIYZIHGNSA-N (E)-acetamiprid Chemical compound N#C/N=C(\C)N(C)CC1=CC=C(Cl)N=C1 WCXDHFDTOYPNIE-RIYZIHGNSA-N 0.000 description 1
- ZFHGXWPMULPQSE-SZGBIDFHSA-N (Z)-(1S)-cis-tefluthrin Chemical compound FC1=C(F)C(C)=C(F)C(F)=C1COC(=O)[C@@H]1C(C)(C)[C@@H]1\C=C(/Cl)C(F)(F)F ZFHGXWPMULPQSE-SZGBIDFHSA-N 0.000 description 1
- LNJXZKBHJZAIKQ-UHFFFAOYSA-N 1,1,1,2-tetrachloro-3-(2,3,3,3-tetrachloropropoxy)propane Chemical compound ClC(Cl)(Cl)C(Cl)COCC(Cl)C(Cl)(Cl)Cl LNJXZKBHJZAIKQ-UHFFFAOYSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GJUABKCEXOMRPQ-UHFFFAOYSA-N 1-[(2,5-dimethoxyphenyl)diazenyl]naphthalen-2-ol Chemical compound COC1=CC=C(OC)C(N=NC=2C3=CC=CC=C3C=CC=2O)=C1 GJUABKCEXOMRPQ-UHFFFAOYSA-N 0.000 description 1
- XCOKKVWDJYSCRZ-UHFFFAOYSA-N 1-phenoxy-3-[(3-phenoxyphenyl)methoxymethyl]benzene Chemical compound C=1C=CC(OC=2C=CC=CC=2)=CC=1COCC(C=1)=CC=CC=1OC1=CC=CC=C1 XCOKKVWDJYSCRZ-UHFFFAOYSA-N 0.000 description 1
- FMTFEIJHMMQUJI-NJAFHUGGSA-N 102130-98-3 Natural products CC=CCC1=C(C)[C@H](CC1=O)OC(=O)[C@@H]1[C@@H](C=C(C)C)C1(C)C FMTFEIJHMMQUJI-NJAFHUGGSA-N 0.000 description 1
- ZWBANJRSWNLUEP-UHFFFAOYSA-N 2,2,2-trichloro-1,1-bis(2-chlorophenyl)ethanol Chemical compound C=1C=CC=C(Cl)C=1C(C(Cl)(Cl)Cl)(O)C1=CC=CC=C1Cl ZWBANJRSWNLUEP-UHFFFAOYSA-N 0.000 description 1
- SFHVXKNMCGSLAR-UHFFFAOYSA-N 2,2,3,3-tetramethylcyclopropanecarboxylic acid Chemical compound CC1(C)C(C(O)=O)C1(C)C SFHVXKNMCGSLAR-UHFFFAOYSA-N 0.000 description 1
- SPSPIUSUWPLVKD-UHFFFAOYSA-N 2,3-dibutyl-6-methylphenol Chemical compound CCCCC1=CC=C(C)C(O)=C1CCCC SPSPIUSUWPLVKD-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- IMOYOUMVYICGCA-UHFFFAOYSA-N 2-tert-butyl-4-hydroxyanisole Chemical compound COC1=CC=C(O)C=C1C(C)(C)C IMOYOUMVYICGCA-UHFFFAOYSA-N 0.000 description 1
- AZSNMRSAGSSBNP-UHFFFAOYSA-N 22,23-dihydroavermectin B1a Natural products C1CC(C)C(C(C)CC)OC21OC(CC=C(C)C(OC1OC(C)C(OC3OC(C)C(O)C(OC)C3)C(OC)C1)C(C)C=CC=C1C3(C(C(=O)O4)C=C(C)C(O)C3OC1)O)CC4C2 AZSNMRSAGSSBNP-UHFFFAOYSA-N 0.000 description 1
- UOYIYWCAYFTQLH-UHFFFAOYSA-N 3,7-dinitro-1,3,5,7-tetrazabicyclo[3.3.1]nonane Chemical compound C1N2CN([N+](=O)[O-])CN1CN([N+]([O-])=O)C2 UOYIYWCAYFTQLH-UHFFFAOYSA-N 0.000 description 1
- CSXOGACWYJFTLV-UHFFFAOYSA-N 4-methyl-5-propyl-1,3-benzodioxole Chemical compound CCCC1=CC=C2OCOC2=C1C CSXOGACWYJFTLV-UHFFFAOYSA-N 0.000 description 1
- IBSREHMXUMOFBB-JFUDTMANSA-N 5u8924t11h Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C(C)C)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 IBSREHMXUMOFBB-JFUDTMANSA-N 0.000 description 1
- SPBDXSGPUHCETR-JFUDTMANSA-N 8883yp2r6d Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O[C@@H]([C@@H](C)CC4)C(C)C)O3)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1C[C@H](C)[C@@H]([C@@H](C)CC)O[C@@]21O[C@H](C\C=C(C)\[C@@H](O[C@@H]1O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C1)[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 SPBDXSGPUHCETR-JFUDTMANSA-N 0.000 description 1
- 239000005660 Abamectin Substances 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- 241000132121 Acaridae Species 0.000 description 1
- 239000005875 Acetamiprid Substances 0.000 description 1
- 239000005652 Acrinathrin Substances 0.000 description 1
- 241000175828 Adoxophyes orana Species 0.000 description 1
- 241000256111 Aedes <genus> Species 0.000 description 1
- 241000256118 Aedes aegypti Species 0.000 description 1
- 241000256173 Aedes albopictus Species 0.000 description 1
- 241000218473 Agrotis Species 0.000 description 1
- 241000566547 Agrotis ipsilon Species 0.000 description 1
- 241000218475 Agrotis segetum Species 0.000 description 1
- 241000254124 Aleyrodidae Species 0.000 description 1
- 244000291564 Allium cepa Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- 241001105153 Anobiidae Species 0.000 description 1
- 241000519878 Anomala rufocuprea Species 0.000 description 1
- 241000256186 Anopheles <genus> Species 0.000 description 1
- 241001279740 Anopheles sinensis Species 0.000 description 1
- 241001427556 Anoplura Species 0.000 description 1
- 241000254177 Anthonomus Species 0.000 description 1
- 241000254175 Anthonomus grandis Species 0.000 description 1
- 241001177135 Anthrenus verbasci Species 0.000 description 1
- 241000002026 Apamea apamiformis Species 0.000 description 1
- 241001600408 Aphis gossypii Species 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 241000238421 Arthropoda Species 0.000 description 1
- 241000447770 Athalia japonica Species 0.000 description 1
- 241000131286 Attagenus Species 0.000 description 1
- 241000902805 Aulacophora Species 0.000 description 1
- 239000005878 Azadirachtin Substances 0.000 description 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
- 241001124657 Bethylidae Species 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- 235000011303 Brassica alboglabra Nutrition 0.000 description 1
- 235000011302 Brassica oleracea Nutrition 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
- 240000004160 Capsicum annuum Species 0.000 description 1
- 235000008534 Capsicum annuum var annuum Nutrition 0.000 description 1
- 241001347514 Carposinidae Species 0.000 description 1
- 241001481710 Cerambycidae Species 0.000 description 1
- 241000134426 Ceratopogonidae Species 0.000 description 1
- 150000000703 Cerium Chemical class 0.000 description 1
- 241001177891 Cheyletidae Species 0.000 description 1
- 241001279148 Cheyletus Species 0.000 description 1
- 241001279151 Cheyletus malaccensis Species 0.000 description 1
- 241000426497 Chilo suppressalis Species 0.000 description 1
- 241000255930 Chironomidae Species 0.000 description 1
- 239000005944 Chlorpyrifos Substances 0.000 description 1
- 241000934018 Chortoglyphidae Species 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 241000098289 Cnaphalocrocis medinalis Species 0.000 description 1
- 241001415288 Coccidae Species 0.000 description 1
- 241000255749 Coccinellidae Species 0.000 description 1
- 241001509962 Coptotermes formosanus Species 0.000 description 1
- 241000490513 Ctenocephalides canis Species 0.000 description 1
- 241000258924 Ctenocephalides felis Species 0.000 description 1
- 241000256054 Culex <genus> Species 0.000 description 1
- 241000256059 Culex pipiens Species 0.000 description 1
- 241000144210 Culex pipiens pallens Species 0.000 description 1
- 241000256060 Culex tritaeniorhynchus Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000005946 Cypermethrin Substances 0.000 description 1
- 239000004287 Dehydroacetic acid Substances 0.000 description 1
- 241001466044 Delphacidae Species 0.000 description 1
- 239000005892 Deltamethrin Substances 0.000 description 1
- 241001481702 Dermanyssidae Species 0.000 description 1
- 241000238710 Dermatophagoides Species 0.000 description 1
- 241000238713 Dermatophagoides farinae Species 0.000 description 1
- 241000489975 Diabrotica Species 0.000 description 1
- 241000489977 Diabrotica virgifera Species 0.000 description 1
- 241000489947 Diabrotica virgifera virgifera Species 0.000 description 1
- 241000709823 Dictyoptera <beetle genus> Species 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- CTZNINKRTKCWGU-UHFFFAOYSA-N Dinactin Natural products CC1C(=O)OC(C)CC(O2)CCC2C(C)C(=O)OC(CC)CC(O2)CCC2C(C)C(=O)OC(CC)CC(O2)CCC2C(C)C(=O)OC(C)CC2CCC1O2 CTZNINKRTKCWGU-UHFFFAOYSA-N 0.000 description 1
- 241000255581 Drosophila <fruit fly, genus> Species 0.000 description 1
- 241000255582 Drosophilidae Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- YUGWDVYLFSETPE-JLHYYAGUSA-N Empenthrin Chemical compound CC\C=C(/C)C(C#C)OC(=O)C1C(C=C(C)C)C1(C)C YUGWDVYLFSETPE-JLHYYAGUSA-N 0.000 description 1
- 241001301805 Epilachna Species 0.000 description 1
- 239000005895 Esfenvalerate Substances 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 239000005896 Etofenprox Substances 0.000 description 1
- HMIBKHHNXANVHR-UHFFFAOYSA-N Fenothiocarb Chemical compound CN(C)C(=O)SCCCCOC1=CC=CC=C1 HMIBKHHNXANVHR-UHFFFAOYSA-N 0.000 description 1
- 239000005657 Fenpyroximate Substances 0.000 description 1
- PNVJTZOFSHSLTO-UHFFFAOYSA-N Fenthion Chemical compound COP(=S)(OC)OC1=CC=C(SC)C(C)=C1 PNVJTZOFSHSLTO-UHFFFAOYSA-N 0.000 description 1
- 241001507629 Formicidae Species 0.000 description 1
- 241001256156 Frankliniella minuta Species 0.000 description 1
- 241000927584 Frankliniella occidentalis Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 108010068370 Glutens Proteins 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 241001645378 Glycyphagidae Species 0.000 description 1
- 241001510533 Glycyphagus Species 0.000 description 1
- 241001510515 Glycyphagus domesticus Species 0.000 description 1
- 241001568505 Gryllotalpa orientalis Species 0.000 description 1
- 241000179420 Haemaphysalis longicornis Species 0.000 description 1
- 241001108896 Haplochthoniidae Species 0.000 description 1
- 241000255990 Helicoverpa Species 0.000 description 1
- 241000256257 Heliothis Species 0.000 description 1
- 241001299253 Henosepilachna vigintioctopunctata Species 0.000 description 1
- 235000005206 Hibiscus Nutrition 0.000 description 1
- 235000007185 Hibiscus lunariifolius Nutrition 0.000 description 1
- 244000284380 Hibiscus rosa sinensis Species 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical class C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- 241000256602 Isoptera Species 0.000 description 1
- 241000238889 Ixodidae Species 0.000 description 1
- 241001510164 Lepidoglyphus destructor Species 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- 241001177141 Lyctinae Species 0.000 description 1
- 241001124557 Lymantriidae Species 0.000 description 1
- 241001190778 Lyonetiidae Species 0.000 description 1
- 239000005949 Malathion Substances 0.000 description 1
- 241000555303 Mamestra brassicae Species 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 241000254043 Melolonthinae Species 0.000 description 1
- LMXFTMYMHGYJEI-UHFFFAOYSA-N Menthoglycol Natural products CC1CCC(C(C)(C)O)C(O)C1 LMXFTMYMHGYJEI-UHFFFAOYSA-N 0.000 description 1
- 239000005916 Methomyl Substances 0.000 description 1
- 239000005918 Milbemectin Substances 0.000 description 1
- 241001477928 Mythimna Species 0.000 description 1
- 241001477931 Mythimna unipuncta Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 241000961933 Nephotettix virescens Species 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 241000256259 Noctuidae Species 0.000 description 1
- ZOKFGVMLEMGULX-UHFFFAOYSA-N OCCC1N(CCCC1)C1=C(C(=NC=C1)C(=O)O)C(CC)C Chemical compound OCCC1N(CCCC1)C1=C(C(=NC=C1)C(=O)O)C(CC)C ZOKFGVMLEMGULX-UHFFFAOYSA-N 0.000 description 1
- 241000238633 Odonata Species 0.000 description 1
- 241000238814 Orthoptera Species 0.000 description 1
- 241001570894 Oulema oryzae Species 0.000 description 1
- 239000005950 Oxamyl Substances 0.000 description 1
- 241000751898 Paederus fuscipes Species 0.000 description 1
- 241000488581 Panonychus citri Species 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 241000517307 Pediculus humanus Species 0.000 description 1
- 241000320508 Pentatomidae Species 0.000 description 1
- 241000238661 Periplaneta Species 0.000 description 1
- 244000220503 Persea thunbergii Species 0.000 description 1
- 235000004267 Persea thunbergii Nutrition 0.000 description 1
- 241000286209 Phasianidae Species 0.000 description 1
- 241001489682 Phoridae Species 0.000 description 1
- 241000255969 Pieris brassicae Species 0.000 description 1
- 241000907661 Pieris rapae Species 0.000 description 1
- 241000595629 Plodia interpunctella Species 0.000 description 1
- 241000368737 Plusiinae Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 241000255131 Psychodidae Species 0.000 description 1
- 241000517304 Pthirus pubis Species 0.000 description 1
- 241000718000 Pulex irritans Species 0.000 description 1
- 241000255893 Pyralidae Species 0.000 description 1
- 241000219492 Quercus Species 0.000 description 1
- 241000866500 Reticulitermes speratus Species 0.000 description 1
- ISRUGXGCCGIOQO-UHFFFAOYSA-N Rhoden Chemical compound CNC(=O)OC1=CC=CC=C1OC(C)C ISRUGXGCCGIOQO-UHFFFAOYSA-N 0.000 description 1
- OUNSASXJZHBGAI-UHFFFAOYSA-N Salithion Chemical compound C1=CC=C2OP(OC)(=S)OCC2=C1 OUNSASXJZHBGAI-UHFFFAOYSA-N 0.000 description 1
- 241000257185 Sarcophagidae Species 0.000 description 1
- 241000256103 Simuliidae Species 0.000 description 1
- 241000239391 Sinoxylon anale Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 240000006394 Sorghum bicolor Species 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- 241000985245 Spodoptera litura Species 0.000 description 1
- 241001157802 Staphylinidae Species 0.000 description 1
- 241001177161 Stegobium paniceum Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 241000255628 Tabanidae Species 0.000 description 1
- 241000916145 Tarsonemidae Species 0.000 description 1
- 239000005658 Tebufenpyrad Substances 0.000 description 1
- 239000005938 Teflubenzuron Substances 0.000 description 1
- 239000005939 Tefluthrin Substances 0.000 description 1
- 241001124685 Tenthredinidae Species 0.000 description 1
- NKNPHSJWQZXWIX-DCVDGXQQSA-N Tetranactin Chemical compound C[C@H]([C@H]1CC[C@H](O1)C[C@@H](OC(=O)[C@@H](C)[C@@H]1CC[C@@H](O1)C[C@@H](CC)OC(=O)[C@H](C)[C@H]1CC[C@H](O1)C[C@H](CC)OC(=O)[C@H]1C)CC)C(=O)O[C@H](CC)C[C@H]2CC[C@@H]1O2 NKNPHSJWQZXWIX-DCVDGXQQSA-N 0.000 description 1
- NKNPHSJWQZXWIX-UHFFFAOYSA-N Tetranactin Natural products CC1C(=O)OC(CC)CC(O2)CCC2C(C)C(=O)OC(CC)CC(O2)CCC2C(C)C(=O)OC(CC)CC(O2)CCC2C(C)C(=O)OC(CC)CC2CCC1O2 NKNPHSJWQZXWIX-UHFFFAOYSA-N 0.000 description 1
- 241001454293 Tetranychus urticae Species 0.000 description 1
- 241000365765 Thrips hawaiiensis Species 0.000 description 1
- 241000339373 Thrips palmi Species 0.000 description 1
- 241001414989 Thysanoptera Species 0.000 description 1
- 241000130771 Tinea pellionella Species 0.000 description 1
- 241000333689 Tineola Species 0.000 description 1
- 241000333690 Tineola bisselliella Species 0.000 description 1
- 241000663810 Tingidae Species 0.000 description 1
- 241000255901 Tortricidae Species 0.000 description 1
- 241000611866 Tyrophagus putrescentiae Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 241000256856 Vespidae Species 0.000 description 1
- 240000004922 Vigna radiata Species 0.000 description 1
- 235000010721 Vigna radiata var radiata Nutrition 0.000 description 1
- 235000011469 Vigna radiata var sublobata Nutrition 0.000 description 1
- 240000001417 Vigna umbellata Species 0.000 description 1
- 235000011453 Vigna umbellata Nutrition 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 1
- DPJITPZADZSLBP-OLZOCXBDSA-N [2,3,5,6-tetrafluoro-4-(methoxymethyl)phenyl]methyl (1r,3r)-3-(2-cyanoprop-1-enyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound FC1=C(F)C(COC)=C(F)C(F)=C1COC(=O)[C@H]1C(C)(C)[C@@H]1C=C(C)C#N DPJITPZADZSLBP-OLZOCXBDSA-N 0.000 description 1
- 229950008167 abamectin Drugs 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- YASYVMFAVPKPKE-UHFFFAOYSA-N acephate Chemical compound COP(=O)(SC)NC(C)=O YASYVMFAVPKPKE-UHFFFAOYSA-N 0.000 description 1
- YLFSVIMMRPNPFK-WEQBUNFVSA-N acrinathrin Chemical compound CC1(C)[C@@H](\C=C/C(=O)OC(C(F)(F)F)C(F)(F)F)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YLFSVIMMRPNPFK-WEQBUNFVSA-N 0.000 description 1
- QGLZXHRNAYXIBU-WEVVVXLNSA-N aldicarb Chemical compound CNC(=O)O\N=C\C(C)(C)SC QGLZXHRNAYXIBU-WEVVVXLNSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052977 alkali metal sulfide Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000002009 alkene group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 229940024113 allethrin Drugs 0.000 description 1
- 125000000746 allylic group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229940009868 aluminum magnesium silicate Drugs 0.000 description 1
- LEWCAQWVBYTPMP-UHFFFAOYSA-K aluminum;magnesium;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [Mg+2].[Al+3].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O LEWCAQWVBYTPMP-UHFFFAOYSA-K 0.000 description 1
- WMGSQTMJHBYJMQ-UHFFFAOYSA-N aluminum;magnesium;silicate Chemical compound [Mg+2].[Al+3].[O-][Si]([O-])([O-])[O-] WMGSQTMJHBYJMQ-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000002269 analeptic agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- VEHPJKVTJQSSKL-UHFFFAOYSA-N azadirachtin Natural products O1C2(C)C(C3(C=COC3O3)O)CC3C21C1(C)C(O)C(OCC2(OC(C)=O)C(CC3OC(=O)C(C)=CC)OC(C)=O)C2C32COC(C(=O)OC)(O)C12 VEHPJKVTJQSSKL-UHFFFAOYSA-N 0.000 description 1
- FTNJWQUOZFUQQJ-IRYYUVNJSA-N azadirachtin A Natural products C([C@@H]([C@]1(C=CO[C@H]1O1)O)[C@]2(C)O3)[C@H]1[C@]23[C@]1(C)[C@H](O)[C@H](OC[C@@]2([C@@H](C[C@@H]3OC(=O)C(\C)=C/C)OC(C)=O)C(=O)OC)[C@@H]2[C@]32CO[C@@](C(=O)OC)(O)[C@@H]12 FTNJWQUOZFUQQJ-IRYYUVNJSA-N 0.000 description 1
- FTNJWQUOZFUQQJ-NDAWSKJSSA-N azadirachtin A Chemical compound C([C@@H]([C@]1(C=CO[C@H]1O1)O)[C@]2(C)O3)[C@H]1[C@]23[C@]1(C)[C@H](O)[C@H](OC[C@@]2([C@@H](C[C@@H]3OC(=O)C(\C)=C\C)OC(C)=O)C(=O)OC)[C@@H]2[C@]32CO[C@@](C(=O)OC)(O)[C@@H]12 FTNJWQUOZFUQQJ-NDAWSKJSSA-N 0.000 description 1
- CJJOSEISRRTUQB-UHFFFAOYSA-N azinphos-methyl Chemical group C1=CC=C2C(=O)N(CSP(=S)(OC)OC)N=NC2=C1 CJJOSEISRRTUQB-UHFFFAOYSA-N 0.000 description 1
- FYZBOYWSHKHDMT-UHFFFAOYSA-N benfuracarb Chemical compound CCOC(=O)CCN(C(C)C)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 FYZBOYWSHKHDMT-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 235000021329 brown rice Nutrition 0.000 description 1
- 239000004067 bulking agent Substances 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- BVFSYZFXJYAPQJ-UHFFFAOYSA-N butyl(oxo)tin Chemical compound CCCC[Sn]=O BVFSYZFXJYAPQJ-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 239000001511 capsicum annuum Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229960005286 carbaryl Drugs 0.000 description 1
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- JLQUFIHWVLZVTJ-UHFFFAOYSA-N carbosulfan Chemical compound CCCCN(CCCC)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 JLQUFIHWVLZVTJ-UHFFFAOYSA-N 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910001567 cementite Inorganic materials 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- 238000006757 chemical reactions by type Methods 0.000 description 1
- UISUNVFOGSJSKD-UHFFFAOYSA-N chlorfluazuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC(C=C1Cl)=CC(Cl)=C1OC1=NC=C(C(F)(F)F)C=C1Cl UISUNVFOGSJSKD-UHFFFAOYSA-N 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical class [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- SCKHCCSZFPSHGR-UHFFFAOYSA-N cyanophos Chemical compound COP(=S)(OC)OC1=CC=C(C#N)C=C1 SCKHCCSZFPSHGR-UHFFFAOYSA-N 0.000 description 1
- 150000001942 cyclopropanes Chemical class 0.000 description 1
- LSFUGNKKPMBOMG-UHFFFAOYSA-N cycloprothrin Chemical compound ClC1(Cl)CC1(C=1C=CC=CC=1)C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 LSFUGNKKPMBOMG-UHFFFAOYSA-N 0.000 description 1
- 229960001591 cyfluthrin Drugs 0.000 description 1
- QQODLKZGRKWIFG-QSFXBCCZSA-N cyfluthrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@@H](C#N)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 QQODLKZGRKWIFG-QSFXBCCZSA-N 0.000 description 1
- ZXQYGBMAQZUVMI-UNOMPAQXSA-N cyhalothrin Chemical compound CC1(C)C(\C=C(/Cl)C(F)(F)F)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-UNOMPAQXSA-N 0.000 description 1
- 229960005424 cypermethrin Drugs 0.000 description 1
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 description 1
- 229960002483 decamethrin Drugs 0.000 description 1
- JEQRBTDTEKWZBW-UHFFFAOYSA-N dehydroacetic acid Chemical compound CC(=O)C1=C(O)OC(C)=CC1=O JEQRBTDTEKWZBW-UHFFFAOYSA-N 0.000 description 1
- 235000019258 dehydroacetic acid Nutrition 0.000 description 1
- 229940061632 dehydroacetic acid Drugs 0.000 description 1
- PGRHXDWITVMQBC-UHFFFAOYSA-N dehydroacetic acid Natural products CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 description 1
- OWZREIFADZCYQD-NSHGMRRFSA-N deltamethrin Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OWZREIFADZCYQD-NSHGMRRFSA-N 0.000 description 1
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 1
- OEBRKCOSUFCWJD-UHFFFAOYSA-N dichlorvos Chemical compound COP(=O)(OC)OC=C(Cl)Cl OEBRKCOSUFCWJD-UHFFFAOYSA-N 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical class NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- JXSJBGJIGXNWCI-UHFFFAOYSA-N diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 0.000 description 1
- 235000001916 dieting Nutrition 0.000 description 1
- 230000037228 dieting effect Effects 0.000 description 1
- WZPMZMCZAGFKOC-UHFFFAOYSA-N diisopropyl hydrogen phosphate Chemical compound CC(C)OP(O)(=O)OC(C)C WZPMZMCZAGFKOC-UHFFFAOYSA-N 0.000 description 1
- ZBDGIMZKOJALMU-MVWQHRGOSA-N dinactin Chemical compound C[C@@H]([C@@H]1CC[C@@H](O1)C[C@@H](OC(=O)[C@@H](C)[C@H]1CC[C@H](O1)C[C@@H](C)OC(=O)[C@@H](C)[C@@H]1CC[C@@H](O1)C[C@H](CC)OC(=O)[C@H]1C)CC)C(=O)O[C@H](C)C[C@@H]2CC[C@H]1O2 ZBDGIMZKOJALMU-MVWQHRGOSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- DOFZAZXDOSGAJZ-UHFFFAOYSA-N disulfoton Chemical compound CCOP(=S)(OCC)SCCSCC DOFZAZXDOSGAJZ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 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 description 1
- HCZKYJDFEPMADG-UHFFFAOYSA-N erythro-nordihydroguaiaretic acid Natural products C=1C=C(O)C(O)=CC=1CC(C)C(C)CC1=CC=C(O)C(O)=C1 HCZKYJDFEPMADG-UHFFFAOYSA-N 0.000 description 1
- NYPJDWWKZLNGGM-RPWUZVMVSA-N esfenvalerate Chemical compound C=1C([C@@H](C#N)OC(=O)[C@@H](C(C)C)C=2C=CC(Cl)=CC=2)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-RPWUZVMVSA-N 0.000 description 1
- HEZNVIYQEUHLNI-UHFFFAOYSA-N ethiofencarb Chemical compound CCSCC1=CC=CC=C1OC(=O)NC HEZNVIYQEUHLNI-UHFFFAOYSA-N 0.000 description 1
- RIZMRRKBZQXFOY-UHFFFAOYSA-N ethion Chemical compound CCOP(=S)(OCC)SCSP(=S)(OCC)OCC RIZMRRKBZQXFOY-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- YREQHYQNNWYQCJ-UHFFFAOYSA-N etofenprox Chemical compound C1=CC(OCC)=CC=C1C(C)(C)COCC1=CC=CC(OC=2C=CC=CC=2)=C1 YREQHYQNNWYQCJ-UHFFFAOYSA-N 0.000 description 1
- 229950005085 etofenprox Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- ZNOLGFHPUIJIMJ-UHFFFAOYSA-N fenitrothion Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C(C)=C1 ZNOLGFHPUIJIMJ-UHFFFAOYSA-N 0.000 description 1
- DIRFUJHNVNOBMY-UHFFFAOYSA-N fenobucarb Chemical compound CCC(C)C1=CC=CC=C1OC(=O)NC DIRFUJHNVNOBMY-UHFFFAOYSA-N 0.000 description 1
- XQUXKZZNEFRCAW-UHFFFAOYSA-N fenpropathrin Chemical compound CC1(C)C(C)(C)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 XQUXKZZNEFRCAW-UHFFFAOYSA-N 0.000 description 1
- YYJNOYZRYGDPNH-MFKUBSTISA-N fenpyroximate Chemical compound C=1C=C(C(=O)OC(C)(C)C)C=CC=1CO/N=C/C=1C(C)=NN(C)C=1OC1=CC=CC=C1 YYJNOYZRYGDPNH-MFKUBSTISA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- RYLHNOVXKPXDIP-UHFFFAOYSA-N flufenoxuron Chemical compound C=1C=C(NC(=O)NC(=O)C=2C(=CC=CC=2F)F)C(F)=CC=1OC1=CC=C(C(F)(F)F)C=C1Cl RYLHNOVXKPXDIP-UHFFFAOYSA-N 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 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 description 1
- 239000000499 gel Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 235000021312 gluten Nutrition 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-M hydrosulfide Chemical compound [SH-] RWSOTUBLDIXVET-UHFFFAOYSA-M 0.000 description 1
- 239000001735 hyssopus officinalis l. herb oil Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- 229960002418 ivermectin Drugs 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 229960000453 malathion Drugs 0.000 description 1
- 229960003951 masoprocol Drugs 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- MEBQXILRKZHVCX-UHFFFAOYSA-N methidathion Chemical compound COC1=NN(CSP(=S)(OC)OC)C(=O)S1 MEBQXILRKZHVCX-UHFFFAOYSA-N 0.000 description 1
- UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 description 1
- 229960001952 metrifonate Drugs 0.000 description 1
- ZLBGSRMUSVULIE-GSMJGMFJSA-N milbemycin A3 Chemical compound O1[C@H](C)[C@@H](C)CC[C@@]11O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 ZLBGSRMUSVULIE-GSMJGMFJSA-N 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- WLLGXSLBOPFWQV-OTHKPKEBSA-N molport-035-783-878 Chemical compound C([C@H]1C=C2)[C@H]2C2C1C(=O)N(CC(CC)CCCC)C2=O WLLGXSLBOPFWQV-OTHKPKEBSA-N 0.000 description 1
- KRTSDMXIXPKRQR-AATRIKPKSA-N monocrotophos Chemical compound CNC(=O)\C=C(/C)OP(=O)(OC)OC KRTSDMXIXPKRQR-AATRIKPKSA-N 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- YFKNCTBAPAZLON-UHFFFAOYSA-N n,n-dimethyl-1h-indol-2-amine Chemical compound C1=CC=C2NC(N(C)C)=CC2=C1 YFKNCTBAPAZLON-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 230000000422 nocturnal effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- KZAUOCCYDRDERY-UHFFFAOYSA-N oxamyl Chemical compound CNC(=O)ON=C(SC)C(=O)N(C)C KZAUOCCYDRDERY-UHFFFAOYSA-N 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 229960000490 permethrin Drugs 0.000 description 1
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
- 150000008048 phenylpyrazoles Chemical class 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- VKJKEPKFPUWCAS-UHFFFAOYSA-M potassium chlorate Chemical compound [K+].[O-]Cl(=O)=O VKJKEPKFPUWCAS-UHFFFAOYSA-M 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- SMKRKQBMYOFFMU-UHFFFAOYSA-N prallethrin Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OC1C(C)=C(CC#C)C(=O)C1 SMKRKQBMYOFFMU-UHFFFAOYSA-N 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- ITKAIUGKVKDENI-UHFFFAOYSA-N pyrimidifen Chemical compound CC1=C(C)C(CCOCC)=CC=C1OCCNC1=NC=NC(CC)=C1Cl ITKAIUGKVKDENI-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 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
- 230000035484 reaction time Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229940108410 resmethrin Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- HPYNBECUCCGGPA-UHFFFAOYSA-N silafluofen Chemical compound C1=CC(OCC)=CC=C1[Si](C)(C)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 HPYNBECUCCGGPA-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- DDVNRFNDOPPVQJ-HQJQHLMTSA-N transfluthrin Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=C(F)C(F)=CC(F)=C1F DDVNRFNDOPPVQJ-HQJQHLMTSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- DFQMKYUSAALDDY-MQEBUAKTSA-N trinactin Chemical compound C[C@@H]([C@@H]1CC[C@@H](O1)C[C@H](OC(=O)[C@H](C)[C@H]1CC[C@H](O1)C[C@H](CC)OC(=O)[C@@H](C)[C@@H]1CC[C@@H](O1)C[C@@H](CC)OC(=O)[C@@H]1C)CC)C(=O)O[C@@H](C)C[C@@H]2CC[C@H]1O2 DFQMKYUSAALDDY-MQEBUAKTSA-N 0.000 description 1
- DFQMKYUSAALDDY-UHFFFAOYSA-N trinactin Natural products CC1C(=O)OC(CC)CC(O2)CCC2C(C)C(=O)OC(CC)CC(O2)CCC2C(C)C(=O)OC(CC)CC(O2)CCC2C(C)C(=O)OC(C)CC2CCC1O2 DFQMKYUSAALDDY-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/31—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本發明係關於酯化合物與其用途。
EP 0926129 A1述及某種類別的四氟苯甲基酯化合物。
本發明的一項目的為提供具有優良害蟲防治效力的化合物。
本案發明人業經精深研究以找出具有優良害蟲防治效力的化合物,結果,發現後文中式(1)所示之化合物具有優良害蟲防治效力,而完成本發明。
亦即,本發明提供:1.一種式(1)所示之酯化合物(後文中稱為本發明化合物):
其中,R表示C1-C4烷基或C3-C4烯基,且A表示單鍵或氧原子;2.根據上述第1項之酯化合物,其中,A為單鍵;3.根據上述第1項之酯化合物,其中,A為氧原子;4.一種害蟲防治劑,其包含式(1)所示之酯化合物作為活性成分;5.一種防治害蟲的方法,其包括施加有效量的式(1)所示
之酯化合物於害蟲或害蟲棲息之場所;及6.一種式(1)所示之酯化合物於防治害蟲上之用途。
由於本發明化合物具有優良害蟲防治效力,因此其可用為害蟲防治劑的活性成分。
於本發明化合物中,存在有因為在環丙烷環所含兩個不對稱碳原子所導致的異構物以及因雙鍵所導致的異構物,且彼等的每一者與具有隨意比例的此等異構物之混合物都包括在本發明中。
於本發明中,C1-C4烷基的例子包括甲基、乙基、丙基和類似者,且C3-C4烯基的例子包括烯丙基。
本發明化合物的例子包括下列化合物:
一種式(1)所示之化合物,其中,環丙烷環的1-位置所具絕對組態(configuration)為R組態;一種式(1)所示之化合物,其中,在環丙烷環的1-位置之取代基和在環丙烷環的3-位置之取代基所具相對組態為反式組態(trans configuration);一種式(1)所示之化合物,其中,在環丙烷環的1-位置之取代基和在環丙烷環的3-位置之取代基所具相對組態為順式組態(cis configuration);
一種式(1)所示之化合物,其中,在環丙烷環3-位置的取代基所含雙鍵所具相對組態為Z組態;一種式(1)所示之化合物,其中,環丙烷環的1-位置所具絕對組態為R組態,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態;一種式(1)所示之化合物,其中,環丙烷環的1-位置所具絕對組態為R組態,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為順式組態;一種式(1)所示之化合物,其中,環丙烷環的1-位置所具絕對組態為R組態,在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態,且在環丙烷環3-位置的取代基所含雙鍵所具相對組態為Z組態;一種式(1)所示之化合物,其中,環丙烷環的1-位置所具絕對組態為R組態,在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為順式組態,且在環丙烷環3-位置的取代基所含雙鍵所具相對組態為Z組態;一種式(1)所示之化合物,其富含下述化合物;其中,環丙烷環的1-位置所具絕對組態為R組態,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態;一種式(1)所示之化合物,其含有不少於80%的下述化合物,其中,環丙烷環的1-位置所具絕對組態為R組態,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態;
一種式(1)所示之化合物,其含有不少於90%的下述化合物,其中,環丙烷環的1-位置所具絕對組態為R組態,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態;一種式(1)所示之化合物,其中,R為C1-C4烷基;一種式(1)所示之化合物,其中,R為C3-C4烯基;一種式(1)所示之化合物,其中,R為甲基或烯丙基;一種式(1)所示之化合物,其中,A為單鍵;一種式(1)所示之化合物,其中,A為氧原子;一種式(1)所示之化合物,其中,R為C1-C4烷基,且A為單鍵;一種式(1)所示之化合物,其中,R為C1-C4烷基,A為單鍵且環丙烷環的1-位置所具絕對組態為R組態;一種式(1)所示之化合物,其中,R為C1-C4烷基,A為單鍵且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態;一種式(1)所示之化合物,其中,R為C1-C4烷基,A為單鍵,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為順式組態;一種式(1)所示之化合物,其中,R為C1-C4烷基,A為單鍵,且在環丙烷環3-位置的取代基所含雙鍵所具相對組態為Z組態;一種式(1)所示之化合物,其中,R為C1-C4烷基,A為單鍵,環丙烷環的1-位置所具絕對組態為R組態,且在環丙
烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態;一種化合物,其中,R為C1-C4烷基,A為單鍵,環丙烷環的1-位置所具絕對組態為R組態,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為順式組態;一種式(1)所示之化合物,其中,R為C1-C4烷基,A為單鍵,環丙烷環的1-位置所具絕對組態為R組態,在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態,且在環丙烷環3-位置的取代基所含雙鍵所具相對組態為Z組態;一種式(1)所示之化合物,其中,R為C1-C4烷基,A為單鍵,環丙烷環的1-位置所具絕對組態為R組態,在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為順式組態,且在環丙烷環3-位置的取代基所含雙鍵所具相對組態為Z組態;一種式(1)所示之化合物,其富含下述化合物;其中,R為C1-C4烷基,A為單鍵,環丙烷環的1-位置所具絕對組態為R組態,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態;一種式(1)所示之化合物,其含有不少於80%之下述化合物;其中,R為C1-C4烷基,A為單鍵,環丙烷環的1-位置所具絕對組態為R組態,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態;
一種式(1)所示之化合物,其含有不少於90%之下述化合物;其中,R為C1-C4烷基,A為單鍵,環丙烷環的1-位置所具絕對組態為R組態,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態;一種式(1)所示之化合物,其中,R為C3-C4烯基,且A為單鍵;一種式(1)所示之化合物,其中,R為C3-C4烯基,A為單鍵,且環丙烷環的1-位置所具絕對組態為R組態;一種式(1)所示之化合物,其中,R為C3-C4烯基,A為單鍵,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態;一種式(1)所示之化合物,其中,R為C3-C4烯基,A為單鍵,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為順式組態;一種式(1)所示之化合物,其中,R為C3-C4烯基,A為單鍵,且在環丙烷環3-位置的取代基所含雙鍵所具相對組態為Z組態;一種式(1)所示之化合物,其中,R為C3-C4烯基,A為單鍵,環丙烷環的1-位置所具絕對組態為R組態,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態;一種式(1)所示之化合物,其中,R為C3-C4烯基,A為單鍵,環丙烷環的1-位置所具絕對組態為R組態,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相
對組態為順式組態;一種式(1)所示之化合物,其中,R為C3-C4烯基,A為單鍵,環丙烷環的1-位置所具絕對組態為R組態,在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態,且在環丙烷環3-位置的取代基所含雙鍵所具相對組態為Z組態;一種式(1)所示之化合物,其中,R為C3-C4烯基,A為單鍵,環丙烷環的1-位置所具絕對組態為R組態,在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為順式組態,且在環丙烷環3-位置的取代基所含雙鍵所具相對組態為Z組態;一種式(1)所示之化合物,其富含下述化合物;其中,R為C3-C4烯基,A為單鍵,環丙烷環的1-位置所具絕對組態為R組態,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態;一種式(1)所示之化合物,其含有不少於80%之下述化合物;其中,R為C3-C4烯基,A為單鍵,環丙烷環的1-位置所具絕對組態為R組態,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態;一種式(1)所示之化合物,其含有不少於90%之下述化合物;其中,R為C3-C4烯基,A為單鍵,環丙烷環的1-位置所具絕對組態為R組態,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態;一種式(1)所示之化合物,其中,R為C1-C4烷基,且A為
氧原子;一種式(1)所示之化合物,其中,R為C1-C4烷基,A為氧原子,且環丙烷環的1-位置所具絕對組態為R組態;一種式(1)所示之化合物,其中,R為C1-C4烷基,A為氧原子,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態;一種式(1)所示之化合物,其中,R為C1-C4烷基,A為氧原子,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為順式組態;一種式(1)所示之化合物,其中,R為C1-C4烷基,A為氧原子,且在環丙烷環3-位置的取代基所含雙鍵所具相對組態為Z組態;一種式(1)所示之化合物,其中,R為C1-C4烷基,A為氧原子,環丙烷環的1-位置所具絕對組態為R組態,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態;一種式(1)所示之化合物,其中,R為C1-C4烷基,A為氧原子,環丙烷環的1-位置所具絕對組態為R組態,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為順式組態;一種式(1)所示之化合物,其中,R為C1-C4烷基,A為氧原子,環丙烷環的1-位置所具絕對組態為R組態,在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態且在環丙烷環3-位置的取代基所含雙鍵
所具相對組態為Z組態;一種式(1)所示之化合物,其中,R為C1-C4烷基,A為氧原子,環丙烷環的1-位置所具絕對組態為R組態,在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為順式組態且在環丙烷環3-位置的取代基所含雙鍵所具相對組態為Z組態;一種式(1)所示之化合物,其富含下述化合物:其中,R為C1-C4烷基,A為氧原子,環丙烷環的1-位置所具絕對組態為R組態,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態;一種式(1)所示之化合物,其含有不少於80%之下述化合物:其中,R為C1-C4烷基,A為氧原子,環丙烷環的1-位置所具絕對組態為R組態,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態;一種式(1)所示之化合物,其含有不少於90%之下述化合物:其中,R為C1-C4烷基,A為氧原子,環丙烷環的1-位置所具絕對組態為R組態,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態;一種式(1)所示之化合物,其中,R為甲基,且A為單鍵;一種式(1)所示之化合物,其中,R為甲基,A為單鍵,且環丙烷環的1-位置所具絕對組態為R組態;一種式(1)所示之化合物,其中,R為甲基,A為單鍵,且
在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態;一種式(1)所示之化合物,其中,R為甲基,A為單鍵,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為順式組態;一種式(1)所示之化合物,其中,R為甲基,A為單鍵,且在環丙烷環3-位置上的取代基所含雙鍵所具相對組態為Z組態;一種式(1)所示之化合物,其中,R為甲基,A為單鍵,環丙烷環的1-位置所具絕對組態為R組態,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態;一種式(1)所示之化合物,其中,R為甲基,A為單鍵,環丙烷環的1-位置所具絕對組態為R組態,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為順式組態;一種式(1)所示之化合物,其中,R為甲基,A為單鍵,環丙烷環的1-位置所具絕對組態為R組態,在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態且在環丙烷環3-位置的取代基所含雙鍵所具相對組態為Z組態;一種式(1)所示之化合物,其中,R為甲基,A為單鍵,環丙烷環的1-位置所具絕對組態為R組態,在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態
為順式組態且在環丙烷環3-位置的取代基所含雙鍵所具相對組態為Z組態;一種式(1)所示之化合物,其富含下述化合物:其中,R為甲基,A為單鍵,環丙烷環的1-位置所具絕對組態為R組態,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態;一種式(1)所示之化合物,其含有不少於80%之下述化合物:其中,R為甲基,A為單鍵,環丙烷環的1-位置所具絕對組態為R組態,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態;一種式(1)所示之化合物,其含有不少於90%之下述化合物:其中,R為甲基,A為單鍵,環丙烷環的1-位置所具絕對組態為R組態,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態;一種式(1)所示之化合物,其中,R為烯丙基,且A為單鍵;一種式(1)所示之化合物,其中,R為烯丙基,A為單鍵,且環丙烷環的1-位置所具絕對組態為R組態;一種式(1)所示之化合物,其中,R為烯丙基,A為單鍵,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態;一種式(1)所示之化合物,其中,R為烯丙基,A為單鍵,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為順式組態;一種式(1)所示之化合物,其中,R為烯丙基,A為單鍵,
且在環丙烷環3-位置的取代基所含雙鍵所具相對組態為Z組態;一種式(1)所示之化合物,其中,R為烯丙基,A為單鍵,環丙烷環的1-位置所具絕對組態為R組態,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態;一種式(1)所示之化合物,其中,R為烯丙基,A為單鍵,環丙烷環的1-位置所具絕對組態為R組態,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為順式組態;一種式(1)所示之化合物,其中,R為烯丙基,A為單鍵,環丙烷環的1-位置所具絕對組態為R組態,在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態且在環丙烷環3-位置的取代基所含雙鍵所具相對組態為Z組態;一種式(1)所示之化合物,其中,R為烯丙基,A為單鍵,環丙烷環的1-位置所具絕對組態為R組態,在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為順式組態且在環丙烷環3-位置的取代基所含雙鍵所具相對組態為Z組態;一種式(1)所示之化合物,其富含下述化合物:其中,R為烯丙基,A為單鍵,環丙烷環的1-位置所具絕對組態為R組態,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態;
一種式(1)所示之化合物,其含有不少於80%之下述化合物:其中,R為烯丙基,A為單鍵,環丙烷環的1-位置所具絕對組態為R組態,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態;一種式(1)所示之化合物,其含有不少於90%之下述化合物:其中,R為烯丙基,A為單鍵,環丙烷環的1-位置所具絕對組態為R組態,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態;一種式(1)所示之化合物,其中,R為甲基,且A為氧原子;一種式(1)所示之化合物,其中,R為甲基,A為氧原子,且環丙烷環的1-位置所具絕對組態為R組態;一種式(1)所示之化合物,其中,R為甲基,A為氧原子,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態;一種式(1)所示之化合物,其中,R為甲基,A為氧原子,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為順式組態;一種式(1)所示之化合物,其中,R為甲基,A為氧原子,且在環丙烷環3-位置的取代基所含雙鍵所具相對組態為Z組態;一種式(1)所示之化合物,其中,R為甲基,A為氧原子,環丙烷環的1-位置所具絕對組態為R組態,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態;
一種式(1)所示之化合物,其中,R為甲基,A為氧原子,環丙烷環的1-位置所具絕對組態為R組態,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為順式組態;一種式(1)所示之化合物,其中,R為甲基,A為氧原子,環丙烷環的1-位置所具絕對組態為R組態,在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態且在環丙烷環3-位置的取代基所含雙鍵所具相對組態為Z組態;一種式(1)所示之化合物,其中,R為甲基,A為氧原子,環丙烷環的1-位置所具絕對組態為R組態,在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為順式組態且在環丙烷環3-位置的取代基所含雙鍵所具相對組態為Z組態;一種式(1)所示之化合物,其富含下述化合物:其中,R為甲基,A為氧原子,環丙烷環的1-位置所具絕對組態為R組態,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態;一種式(1)所示之化合物,其含有不少於80%之下述化合物:其中,R為甲基,A為氧原子,環丙烷環的1-位置所具絕對組態為R組態,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態;及一種式(1)所示之化合物,其含有不少於90%之下述化合物:其中,R為甲基,A為氧原子,環丙烷環的1-位置所
具絕對組態為R組態,且在環丙烷環1-位置之取代基和在環丙烷環3-位置之取代基所具相對組態為反式組態。
本發明化合物可經由,例如,下述的方法製造。
一種方法,其包括令式(2)所示之醇化合物:
其中,R表C1-C4烷基或C3-C4烯基,且A表單鍵或氧原子;與式(3)所示之羧酸化合物或其衍生物(如酸鹵化物、酸酐等)反應:
通常,此反應係在溶劑內於縮合劑或鹼的存在中進行。
縮合劑的例子包括二環己基碳化二亞胺和1-(3-二甲胺基丙基)-3-乙基碳化二亞胺鹽酸鹽。
鹼的例子包括諸如三乙胺、吡啶、N,N-二乙基苯胺、4-二甲胺基吡啶、和二異丙基乙胺等有機鹼。
溶劑的例子包括烴類,諸如苯、甲苯和己烷;醚類,諸如乙醚和四氫呋喃;和鹵化烴類,諸如二氯甲烷、1,2-二氯乙烷和氯苯。
反應時間通常在5分鐘到72小時的範圍之內。
反應溫度通常在-20℃到100℃的範圍之內(但其限制條件為,當所用溶劑的沸點低於100℃時,則為-20℃至溶劑沸點),較佳者在-5℃到100℃的範圍之內(但其限制條件為,當所用溶劑的沸點低於100℃時,則為-5℃至溶劑沸點)。
於反應中,所使用的式(2)所示之醇化合物,與式(3)所示之羧酸化合物或其反應性衍生物之莫耳比例可經恰當地選擇,不過該反應較佳係在等莫耳比例或接近等莫耳之比例下進行。
通常,相對於1莫耳式(2)所示之醇化合物,縮合劑或鹼可用1莫耳到過量,較佳為1莫耳到5莫耳的恰當比例使用。該縮合劑或鹼係根據特別的式(3)所示之羧酸化合物或其反應性衍生物(例如式(3)所示之羧酸化合物的相應酸氯化物化合物、酸溴化物化合物、酸酐等)之類別而恰當地選擇。
在反應完成之後,對反應混合物施以習用的後-處理程序,例如,過濾反應混合物,接著濃縮所得濾液,或者將反應混合物傾倒在水中,接著用有機溶劑萃取且將萃取液濃縮而得本發明化合物。所得本發明化合物可用習用程序(諸如層析術和蒸餾)予以純化。
式(2)所示之醇化合物為市售產品,或為在EP 0926129 A1和美國專利第4405640號中所述化合物,且可以市售產品之形式購得,或可用此等刊物中所述方法製造。
式(3)所表羧酸化合物為在,例如,Agr. Biol. Chem., 34,
1119(1970)中所述化合物,且可用其中所述方法製造。
本發明化合物對其具有效力的害蟲之例子包括節肢動物,諸如昆蟲和蟎(acarine),特定言之,例如,下列害蟲。
螟蛾科(Pyralidae)諸如二化螟蛾(Chilo suppressalis)(鑽心蟲)、稻縱捲葉野螟蛾(Cnaphalocrocis medinalis)(稻大卷葉螟)、印度穀粉螟蛾(Plodia interpunctella)(印度粉螟)、和類似者;夜蛾科(Noctuidae)諸如斜紋夜蛾(Spodoptera litura)(普通夜盜蟲)、東方黏蟲(Pseudaletia separate)(稻行軍蟲)、甘藍夜蛾(Mamestra brassicae)(甘藍行軍蟲)、和類似者;粉蝶科(Pieridae)諸如紋白蝶(Pieris rapae)(普通菜粉蝶)和類似者;捲蛾科(Tortricidae)諸如茶小捲葉蛾(Adoxophyes orana)和類似者;果蛀蛾科(Carposinidae);潛蛾科(Lyonetiidae);毒蛾科(Lymantriidae);金翅夜蛾亞科(Plusiinae);地老虎屬(Agrotis ssp.)諸如黃地老虎(Agrotis segetum)(行軍蟲)、小地老虎(Agrotis ipsilon)(黑行軍蟲)和類似者;葉蛾屬(Helicoverpa spp.);棉鈴蟲屬(Heliothis spp.);小菜蛾(Plutella xylostella)(鑽石背蛾(diamondback moth));直紋稻弄蝶(Parnara guttata)(rice skipper);負袋衣蛾(Tinea pellionella)(製袋衣蛾(casemaking clothes moth));Tineola bisselliell(織網衣蛾(webbing clothes moth));和類似者;雙翅目(Diptera):蚊科(Calicidae)諸如淡色庫蚊(Culex pipiens pallens)
(普通蚊子)、三斑家蚊(Culex tritaeniorhynchus)和類似者;斑蚊屬(Aedes spp.)諸如埃及斑蚊(Aedes aegypti)、白線斑蚊(Aedes albopictus)和類似者;按蚊屬(Anopheles spp.)諸如中華瘧蚊(Anopheles sinensis)和類似者;搖蚊科(Chironomidae)(搖蚊);家蠅科(Muscidae)諸如普通家蠅(Musca domestica)(家蠅)、廄腐蠅(Muscina stabulans)(false stablefly)、黃腹廄蠅(Fannia canicularis)(小家蠅(lesser housefly))和類似者;麗蠅科(Calliphordiae);麻蠅科(Sarcophagidae);花蠅科(Anthomyiidae)諸如種蠅(Hylemya platura)(seedcorn maggot)、蔥蠅(Delia antique)(onion maggot)和類似者;果實蠅科(Tephritidae)(果蠅);果蠅科(Drosophilidae)(小果蠅);蛾蚋科(Psychodidae)(蛾蚋);蚤蠅科(Phoridae);蚋科(Simuliidae)(蚋);虻科(Tabanidae);螫蠅科(Stomoxyidae)(螫蠅);蠓科(Ceratopogonidae);和類似者;網翅目(Dictyoptera):德國蜚蠊(Blattella germanica)(德國蟑螂)、黑胸大蠊(Periplaneta fuliginosa)(煙褐蟑螂)、美洲蜚蠊(Periplaneta Americana)(美洲蟑螂)、棕色蜚蠊(Periplaneta brunnea)(棕色蟑螂)、東方蜚蠊(Blatta orientalis)(東方蟑螂)和類似者;膜翅目(Hymenoptera):蟻科(Formicidae)(蟻);胡蜂科(Vespidae)(黃蜂);腫腿蜂科(Bethylidae);葉蜂科(Tenthredinidae)諸如黃翅菜葉蜂(Athalia rosae japonensis)(甘藍葉蜂)和類似者;
隠翅目(Aphaniptera):犬蚤(Ctenocephalides canis)、貓蚤(Ctenocephalides felis)、人蚤(Pulex irritans)和類似者;蝨目(Anoplura):頭蝨(Pediculus humanus)、陰蝨(Phthirus pubis)、體蝨(Pediculus humanus humanus)、人體蝨(Pediculus humanus corporis)和類似者;等翅目(Isoptera):黃肢散白蟻(Reticulitermes speratus)、臺灣家白蟻(Coptotermes formosanus)和類似者;半翅目(Hemiptera):飛蝨科(Delphacidae)(飛蝨)諸如斑飛蝨(Laodelphax striatellus)(small brown planthopper)、褐飛虱(Nilaparvata lugens)(褐稻飛虱)、白背飛蝨(Sogatella furcifera)(白背稻飛蝨)和類似者;浮塵子科(Deltocephalidae)(leafaopper)諸如黑尾葉蟬(Nephotettix cincticeps)(青稻葉蟬)、二點黑尾葉蟬(Nephotettix virescens)(青稻葉蟬)和類似者;蚜科(Aphididae)(蚜蟲);椿科(Pentatomidae)(臭蟲);粉蝨科(Aleyrodidae)(粉蝨);軟介殼蟲科(Coccidae)(介殼蟲);軍配蟲科(Tingidae)(軍配蟲);木蝨科(Psyliidae)(木蝨)和類似者;鞘翅目(Coleoptera):姬鰹節蟲(Attagenus japonicus);姬圓鰹節蟲(Anthrenus verbasci);葉甲屬(Diabrotica spp.)(玉米食根蟲
(corn rootworms))諸如玉米根葉甲(Diabrotica virgifera)(西部玉米食根蟲)、十一星瓜葉甲(Diabrotica undecimpunctata howardi)(南方玉米食根蟲(southern corn rootworm))和類似者;金龜子科(Scarabaeidae)諸如金銅金龜(Anomala cuprea)(綠金龜(cupreous chafer))、棒姬金龜(Anomala rufocuprea)(大豆甲蟲(soybeans beetle))和類似者;象鼻蟲科(Curculionidae)諸如玉米象(Sitophilus zeamais)(maize weevil)、稻水象甲(Lissorhoptrus oryzophilus)(rice water weevil)、棉鈴象甲(Anthonomus gradis grandis)(棉花象皮蟲(cottonseed weevil))、綠豆象(Callosobruchuys chienensis)(赤豆象甲(adzuki been weevil))和類似者;擬步甲科(Tenebrionidae)(擬步甲(darkling beetles))諸如黃粉蟲(Tenebrio molitor)(yellow mealworm)、赤擬穀盜(Tribolium castaneum)(red flour beetle)和類似者;金花蟲科(Chrysomelidae)(金花蟲)諸如稻負泥蟲(Oulema oryzae)(稻泥蟲)、黃條葉蚤(Phyllotreta striolata)(striped flea beetle)、黃守瓜(Aulacophora femoralis)(cucurbit leaf beetle)和類似者;竊蠹科(Anobiidae)(藥材甲(drugstore beetles));瓢蟲屬(Epilachna spp.)諸如茄二十八星瓢蟲(Epilachna vigintioctopunctata)(twenty-eight-spotted ladybird)和類似者;粉蠹科(Lyctidae)(粉蠹蟲(powder post beetles));長蠹蟲科(Bostrychidae)(偽粉蠹(false powder post beetles));天牛科(Cerambycidae)(天牛(longhorn beetles));蟻型隱翅蟲(Paederus fuscipes)(隱翅蟲(rove beetles))和類似者;
纓翅目(Thysanoptera):南黃薊馬(Thrips palmi)、西方花薊馬(Frankliniella occidentalis)、花薊馬(Thrips hawaiiensis)(flower thrips)和類似者;直翅目(Orthoptera):螻蛄(Gryllotalpa fossor Scudder)、蝗科(Acrididae)(蝗蟲(grasshopper))和類似者;蜱蟎目(Acarina):皮刺蟎科(Dermanyssidae)諸如美洲塵蟎(Dermatophagoides farinae)、歐洲塵蟎(Dermatophagoides ptrenyssnus)、和類似者;粉蟎科(Acaridae)諸如腐食酪蟎(Tyrophagus putrescentiae)(霉蟎(mold mite))、橢圓嗜粉蟎(Aleuroglyphus ovatus)(brown legged grain mite)和類似者;嗜甜蟎科(Glycyphagidae)諸如嗜甜蟎(Glycyphagus privates)、嗜甜家蟎(Glycyphagus domesticus)、嗜食蟎(Glycyphagus destructor)(groceries mite)和類似者;肉食蟎科(Cheyletidae)諸如馬六甲肉食蟎(Cheyletus malaccensis)、肉食蟎(Cheyletus malaccesis)和類似者;細蟎科(Tarsonemidae);嗜渣蟎科(Chortoglyphidae);禽刺蟎科(Haplochthoniidae);葉蟎科(Tetranychidae)諸如二斑葉蟎(Tetranychus urticae)(二點葉蟎)、神澤葉蟎(Tetranychus kanzawai)(Kanzawa spider mite)、柑桔全爪蟎(Panonychus citri)(柑桔紅蜘蛛)、榆全爪蟎(Panonychus ulmi)(歐洲紅蟎(European red mite))和類似者;硬蜱科(Ixodidae)諸如長角
血蜱(Haemaphysalis longicornis)和類似者。
本發明害蟲防治劑可為本發明化合物本身,或者,通常為包含本發明化合物和惰性載劑的調配物。
調配物的例子包括油溶液、可乳化的濃縮物、可濕粉、可流動的調配物(如水性懸浮液、水性乳液)、灑粉、顆粒、氣霧劑、可加熱揮發的調配物(如殺蟲劑線圈、電加熱的殺蟲劑片、具有加熱用的吸收性蕊的揮發性調配物)、加熱性薰劑(如,自燃型薰劑、化學反應型薰劑、多孔型陶瓷板薰劑等)、非加熱用揮發性調配物(如,樹脂揮發性調配物、浸漬紙揮發性謂配物)、發煙調配物(如,煙霧劑)、ULV調配物和毒餌。
調配方法的例子包括下列方法。
[1]一種方法,其係將本發明化合物與固體載劑、液體載劑、氣體載劑、餌等混合,於需要時加入界面活性劑和其他調配用輔助劑者。
[2]一種方法,其係使本發明化合物滲入不含活性成分的成形固體載劑者。
[3]一種方法,其係將本發明化合物與粉末狀固體載劑混合,且視需要地添加界面活性劑和其他調配用輔助劑,接著將所得混合物成形。
取決於調配物的類型,此等調配物通常含有0.001至95%重量比例的本發明化合物。
調配用的載劑之例子包括固體載劑{黏土(例如高嶺黏土、矽藻土、合成含水二氧化矽、膨潤土、文挾黏土
(Fubasami clay)、和酸性黏土),滑石,陶瓷,其他無機礦物質(如,絹雲母(sericite)、石英、硫磺、活性碳、碳酸鈣、水合氧化矽和蒙脫土),化學肥料(如硫酸銨、磷酸銨、硝酸銨、尿素和氯化銨)等};液體載劑{水、醇(如甲醇和乙醇),酮類(如丙酮和丁酮),芳族烴類(如苯、甲苯、二甲苯、乙苯、甲基萘和苯基二甲苯基乙烷),脂族烴類(如,己烷、環己烷、煤油和氣體油),酯類(如,醋酸乙酯和醋酸丁酯),腈類(如,乙腈和異丁腈),醚類(如,二異丙醚和二氧雜環己烷),酸醯胺類(如,N,N-二甲基甲醯胺和N,N-二甲基乙醯胺),鹵化烴類(如,二氯甲烷、三氯乙烷和四氯化碳),二甲亞碸,植物油(如大豆油和棉籽油)等};及氣體載劑{Flon(氟龍)氣體、丁烷氣體、LPG(液化石油氣)、甲醚、二氧化碳氣體等}。
界面活性劑的例子包括烷基硫酸酯,烷基磺酸鹽,烷基芳基磺酸鹽,烷基芳基醚類,聚氧伸乙基化烷基芳基醚類,聚乙二醇醚類,多元醇酯類和糖醇衍生物。
其他調配用輔助劑的例子包括黏合劑、分散劑和安定劑,例如,酪蛋白、明膠、多醣類(如,澱粉、阿拉伯膠、纖維素衍生物和精胺酸)、木質素衍生物、膨潤土、合成水溶性聚合物(如,聚乙烯醇和聚乙烯吡咯烷酮)、聚丙烯酸、BHT(2,6-二第三丁基-4-甲基酚),和BHA(2-第三丁基-4-甲氧基酚與3-第三丁基-4-甲氧基酚的混合物)。
用於殺蟲劑線圈的固體載劑之例子包括植物粉(諸如木粉、除蟲菊渣(Pyrethrum marc)和類似者),與黏合劑(諸
如塔布(Tabu)粉(豬腳楠(Machilus thunbergii)的粉末)、澱粉、麩質(gluten)和類似者)之混合物。
電加熱型殺昆蟲片所用成形固體載劑之例子包括調製成板狀的棉絨,和調製成板狀的棉絨和紙漿之混合物的細纖維。
自燃型薰劑所用固體載劑之例子包括燃燒熱產生劑,諸如硝酸鹽、亞硝酸鹽、胍鹽、氯酸鉀、硝基纖維素、乙基纖維素、木粉、和類似者;熱分解刺激劑,諸如鹼金屬鹽、鹼土金屬鹽、重鉻酸鹽、鉻酸鹽、和類似者;氧供給劑,諸如硝酸鉀,和類似者;燃燒輔助劑,諸如蜜胺、小麥澱粉、和類似者;膨大劑(bulking agent),諸如矽藻土;和黏合劑,諸如合成糊和類似者。
化學反應型薰劑所用固體載劑之例子包括熱產生劑,諸如鹼金屬硫化物、多硫化物、硫氫化物、氧化鈣和類似者;催化劑,諸如含碳物質、碳化鐵、活性黏土和類似者;有機發泡劑,諸如偶氮二甲醯胺、苯磺醯肼、二硝基五亞甲基四胺、聚苯乙烯、聚胺基甲酸酯和類似者;及填充料,諸如天然纖維片、合成纖維片和類似者。
非加熱型揮發性調配物所用固體載劑之例子包括熱塑性樹脂,和紙(濾紙、日本紙、等)。
毒餌的基本材料之例子包括餌成分,諸如穀粉、植物油、糖、結晶纖維素、和類似者;抗氧化劑,諸如二丁基羥基甲苯、降二氫癒創木酸(nordihydroguaiaretic acid)和類似者;防腐劑,諸如去氫乙酸和類似者;防兒童或寵物誤
食劑,諸如紅辣椒粉;和誘引害蟲香料,諸如乳酪香料、洋蔥香料、花生油、和類似者。
本發明防治害蟲的方法通常係經由將有效量的呈本發明害蟲防治劑形式的本發明化合物施加到害蟲或害蟲棲息場所而實施。
施加本發明害蟲防治劑的方法包括下列方法,且可以依照本發明害蟲防治劑之特定形式、特定使用場所、和類似者而恰當選擇該方法:[1]一種使用本發明害蟲防治劑本身處理害蟲或害蟲棲息場所之方法。
[2]一種將本發明害蟲防治劑用溶劑(諸如水和類似者)予以稀釋,且於其後,將此稀釋溶液噴布到害蟲或害蟲棲息場所之方法。於此情況中,係將通常調配成可乳化濃縮物、可濕粉、可流動劑、微膠囊和類似者之本發明害蟲防治劑稀釋到0.1至10000ppm之濃度。
[3]一種在害蟲棲息場所加熱本發明害蟲防治劑以使活性成分揮發出之方法。
於此情況中,本發明化合物的施用量和施用濃度全部都可依照本發明害蟲防治劑的形式、施用時間、施用場所、施用方法、害蟲類別、損害情勢、和類似者而恰當地決定。
本發明害蟲防治劑可與下列藥劑混合或與下列藥劑一起使用:其他殺昆蟲劑、殺線蟲劑、土壤害蟲防治劑、殺真菌劑、殺草劑、植物生長謂節劑、驅蟲劑(repellent)、增
效劑、肥料、或土壤改質劑。
此等殺昆蟲劑和殺蟎劑的活性成分之例子包括有機磷化合物諸如撲滅松(fenitrothion)、芬殺松(fenthion)、大利松(diazinon)、陶斯松(chlorpyrifos)、毆殺松(acephate)、滅大松(methidathion)、二硫松(disulfoton)、DDVP、硫丙磷(sulprofos)、氰乃松(cyanophos)、蔬果磷(dioxabenzofos)、大滅松(dimethoato)、賽達松(phenthoato)、馬拉松(malathion)、三氯松(trichlorfon)、谷速松(azinphos-methyl)、亞素靈(monocrotophos)、愛殺松(ethion)、和類似者;胺基甲酸酯類化合物諸如BPMC、免扶克(benfuracarb)、安丹(propoxur)、丁基加保扶(carbosulfan)、加保利(carbaryl)、納乃得(methomyl)、乙硫苯威(ethiofencarb)、得滅克(aldicarb)、毆殺滅(oxamyl)、芬硫克(fenothiocarb)、和類似者;合成除蟲菊精類(pyrethroid)化合物諸如醚菊酯(etofenprox)、芬化利(fenvalerate)、益化利(esfenvalerate)、芬普寧(fenpropathrin)、賽滅寧(cypermethrin)、百滅寧(permethrin)、賽洛寧(cyhalothrin)、第滅寧(deltamethrin)、乙氰菊酯(cycloprothrin)、fulvalinate、畢芬寧(biphenthrine)、2-甲基-2-(4-溴二氟甲氧基苯基)丙基(3-苯氧基苯甲基)醚、泰滅寧(tralomethrin)、矽護芬(silafluofen)、苯醚菊酯((d-phenothrin)、賽酚寧(cyphenothrine)、異列滅寧(d-resmethrin)、阿納寧
(acrinathrin)、賽扶寧(cyfluthrin)、七氟菊酯(tefluthrin)、拜富寧(transfluthrin)、治滅寧(tetramethrin)、亞烈寧(allethrin)、右旋炔呋菊酯(d-furamethrin)、普亞列寧(prallethrin)、益避寧(empenthrin)、2,2,3,3-四甲基環丙烷羧酸5-(2-丙炔基)呋喃甲基酯、和類似者;硝基咪唑啶衍生物;N-氰基脒衍生物諸如亞滅培(acetamiprid)、和類似者;氯化烴化合物諸如安殺番(endosulfan)、γ-BHC、1,1-雙(氯苯基)-2,2,2-三氯乙醇、和類似者;苯甲醯基苯基脲化合物諸如克福隆(chlorfluazuron)、得福隆(teflubenzuron)、氟芬隆(flufenoxuron)、和類似者;苯基吡唑化合物;美多代佐(methoxadiazon);新殺蟎(bromopropylate);得脫蟎(tetradifon);靈蟎猛(chinomethionate);畢達本(pyridaben);芬普蟎(fenpyroximate);汰芬隆(diafenthiuron);得芬瑞(tebufenpyrad);瀏陽霉素複劑(polynactin complex)[四活菌素(tetranactin)、二活菌素(dinactin)、三活菌素(trinactin)];畢汰芬(pyrimidifen);密滅汀(milbemectin);阿巴汀(abamectin);愛滅蟲(ivermectin);和印楝素(azadirachtin)。
驅蟲劑的例子包括3,4-蒈烷二醇(3,4-caranediol)、N,N-二乙基-間-甲苯甲醯胺、2-(2-羥基乙基)-1-哌啶羧酸1-甲基丙基酯、對-薄荷烷-3,8-二醇、植物精油諸如海索草油(hyssop oil)、和類似者。
增效劑的例子包括雙-(2,3,3,3-四氯丙基)醚(S-421)、
N-(2-乙基己基)雙環[2.2.1]庚-5-烯-2,3-二甲醯亞胺(MGK-264)、和A-[2-(2-丁氧基乙氧基)乙氧基]-4,5-亞甲二氧基-2-丙基甲苯(丁氧化胡椒基)。
於後文中,要藉由製造例、調配例和試驗例進一步詳細解說本發明,不過本發明不受此等實施例所限制。
首先,顯示本發明製造例。
在氮氣環境下,將0.59克的N,N-二環己基碳化二亞胺加到含0.55克4-甲基-2,3,5,6-四氟苯甲醇、0.51克的(1R)-反-3-(2-氰基-1-丙烯基)-2,2-二甲基環丙烷羧酸、0.10克的4-二甲胺基吡啶和7毫升無水二氯甲烷的混合物內,且在室溫下攪拌該混合物3小時。其後,過濾反應混合物,且在減壓下濃縮濾液。對所得剩餘物施以矽膠管柱層析術而得0.72克的下式(A)所表(1R)-反-3-(2-氰基-1-丙烯基)-2,2-二甲基環丙烷羧酸4-甲基-2,3,5,6-四氟苯甲基酯:
(有關雙鍵的異構物之比例:Z/E=約2/1)(後文中,稱為本發明化合物(1))。
1
H-NMR (CDCl3
, TMS)δ (ppm): 1.21(s, 3H, Z+E異構物),1.32(s, 3H, Z+E異構物),1.71(七,1H, Z+E異構物),1.95(s, 3H, Z+E異構物),2.19(m, 1/3H, E異構物),2.29(s, 3H, Z+E異構物),2.45(m, 2/3H, Z異構物),5.24(s, 2H, Z+E異構物),5.78(d, 2/3H, Z異構物),6.00(d, 1/3H, E異構物)
在氮氣環境下,將0.49克的N,N-二環己基碳化二亞胺加到含0.50克4-甲氧基-2,3,5,6-四氟苯甲醇、0.43克的(1R)-反-3-(2-氰基-1-丙烯基)-2,2-二甲基環丙烷羧酸、0.087克的4-二甲胺基吡啶和7毫升無水二氯甲烷的混合物內,且在室溫下攪拌該混合物3小時。其後,過濾反應混合物,且在減壓下濃縮濾液。對所得剩餘物施以矽膠管柱層析術而得0.62克的下式所表(1R)-反-3-(2-氰基-1-丙烯基)-2,2-二甲基環丙烷羧酸4-甲氧基-2,3,5,6-四氟苯甲基酯:
(有關雙鍵的異構物之比例:Z/E=約2/1)(後文中,稱為本發明化合物(2))。
1
H-NMR (CECl3
, TMS)δ (ppm): 1.21(s, 3H, Z+E異構物),1.31(s, 3H, Z+E異構物),1.72(t, 1H, Z+E異構物),1.96(s, 3H, Z+E異構物),2.19(m, 1/3H, E異構物),2.46(m, 2/3H, Z異構物),4.11(s, 3H, Z+E異構物),5.20(s, 2H, Z+E異構物),5.77(d, 2/3H, Z異構物),6.00(d, 1/3H, E異構物)
在氮氣環境下,將0.23克的1-(3-二甲胺基丙基)-3-乙基碳化二亞胺鹽酸鹽加到含0.20克4-烯丙基-2,3,5,6-四氟苯甲醇、0.16克的(1R)-反-3-(2-氰基-1-丙烯基)-2,2-二甲基環丙烷羧酸、0.05克的4-二甲胺基吡啶和4毫升無水氯仿的混合物內,且在室溫下攪拌該混合物3小時。其後,將反應混合物倒在冰水中,接著用醋酸乙酯萃取兩次。將醋酸乙酯層合併,用飽和氯化鈉水溶液洗滌,以無水硫酸鈉脫水且在減壓下濃縮。對所得剩餘物施以矽膠管柱層析術而得0.32克的下式所表(1R)-反-3-(2-氰基-1-丙烯基)-2,2-二甲基環丙烷羧酸4-烯丙基-2,3,5,6-四氟苯甲基酯:
(有關雙鍵的異構物之比例:Z/E=約2/1)(後文中,稱為本發明化合物(3))。
1
H-NMR (CDCl3
, TMS)δ (ppm): 1.23(s, 3H, Z+E異構物),1.35(s, 3H, Z+E異構物),1.71(t, 1H, Z+E異構物),1.97(s, 3H, Z+E異構物),2.20(m, 1/3H, E異構物),2.46(m, 2/3H, Z異構物),3.49(m, 2H, Z+E異構物),5.10(m, 2H, Z+E異構物),5.23(s, 2H, Z+E異構物),5.79(d, 2/3H, Z異構物),5.88(m, 1H, Z+E異構物),6.00(d, 1/3H, E異構物)
然後,顯示調配例。所有“份數”都是以重量計。
將各20份的本發明化合物(1)至(3)分別溶解到65份二甲苯中,於其中加入15份的Sorpol 3005X(Tobo Chemical Industry Co., LTD.的註冊商標),且攪拌及徹底混合所得混合物而得可乳化的濃縮物。
於各40份的本發明化合物(1)至(3)分別加入5份的Sorpol 3005X,且徹底混合所得混合物。於該混合物中加入32份的CARPLEX #80(合成含水氧化矽,Shionogi & Co., Ltd.的註冊商標)和23份的300網目矽藻土。將所得混合物用果汁混合器攪拌和混合而得可濕粉。
將各1.5份的本發明化合物(1)至(3),1份的TOKUSIL GUN(合成含水氧化矽,為Tokuyama Corp.所製),2份的REAX 85A(木質素磺酸鈉,為Westvaco Chemicals所製),30份的Bentonite FUJI(膨潤土,HOJUN Co., Ltd所製)和
65.5份的SHOKOZAN A Clay(高嶺土,為Shokozan Kogyosho Co.所製)一起研磨且徹底地混合。於其中加入水,且將混合物徹底地捏合,用擠壓造粒機造粒,且乾燥而得到1.5%顆粒。
將各10份的本發明化合物(1)至(3),10份的苯基二甲苯基乙烷和0.5份的SUMIDUR L-75(甲苯二異氰酸酯,為Sumika Bayer Urethane Co., Ltd所製)混合。將所得混合物加到20份的10%阿拉伯膠水溶液,接著用高速攪拌機(homomixer)攪拌而得平均粒徑20微米的乳液。於此乳液中,加入2份的乙二醇,且在60℃的熱浴中進一步攪拌該混合物24小時而得微膠囊漿液。分開地,將0.2份的黃原膠(xanthan gum)和1.0份的VEEGUM R(矽酸鋁鎂,為Sanyo Chemical Industries, Ltd所製)分散在56.3份的離子交換水中而得增稠劑溶液。然後,將42.5份的微膠囊漿液和57.5份的增稠劑溶液混合而得微膠囊化調配物。
將各10份的本發明化合物(1)至(3),和10份的苯基二甲苯基乙烷混合,將所得混合物加到20份的10%聚乙二醇水溶液,接著用高速攪拌機(homomixer)攪拌而得平均粒徑3微米的乳液。分開地,將0.2份的黃原膠和1.0份的VEEGUM R(矽酸鋁鎂,為Sanyo Chemical Industries, Ltd所製)分散在58.8份的離子交換水中而得增稠劑溶液。然後,將10份的乳液和60份的增稠劑溶液混合而得可流動
的調配物。
於各5份的本發明化合物(1)至(3)分別加入3份的CARPLEX #80(合成含水氧化矽細粉,Shionogi & Co., Ltd.的註冊商標),0.3份的PAP(磷酸一異丙基酯和磷酸二異丙基酯的混合物)和91.7份的滑石(300網目),且將所得混合物用果汁混合器攪拌和混合而得灑粉。
將各0.1份的本發明化合物(1)至(3)分別溶解在10份的二氯甲烷中,且將該溶液與89.9份的除臭煤油混合而得油溶液。
將各1份的本發明化合物(1)至(3),5份的二氯甲烷和34份的除臭煤油混合且溶解,並填充到氣霧劑容器內。於接上閥部份之後,在壓力下透過閥部份填充60份的推進劑(液化石油氣體)而得油性氣霧劑。
將經由將各0.6份的本發明化合物(1)至(3),5份的二甲苯,3.4份的除臭煤油和1份的ATMOS 300(乳化劑,為Atlas Chemical Co.的註冊商標),和50份的水混合且溶解所得溶液填充到氣霧劑容器內,且在壓力下透過閥部份填充40份的推進劑(液化石油氣體)而得水性氣霧劑。
將各0.3克的本發明化合物(1)至(3)分別溶解在20毫
升的丙酮中,將該溶液和99.7克的線圈基本材料(經由將塔布粉(Tabu powder),除蟲菊渣和木粉以4:3:3的比例混合所得者)均勻地攪拌和混合,於其中加入100毫升的水,且將該混合物徹底地捏合、模塑、和乾燥而得殺蟲劑線圈。
於各0.8克的本發明化合物(1)至(3)和0.4克丁氧化胡椒基中加入丙酮以溶解彼等且將總體積調整到10毫升。將電熱型殺蟲劑片所用基本材料(將綿絨和紙漿的混合物之細纖維硬化成板狀),2.5公分×1.5公分且厚度為0.3公分,使用0.5毫升該溶液均勻地浸漬而得電熱型殺蟲劑片。
將各3份的本發明化合物(1)至(3)溶解在97份的除臭煤油中而得一溶液,將其放置在聚氯乙烯所製造成的容器之內,且將具有可以用加熱器加熱的上部份之吸收蕊(經由將無機粉末用黏合劑固化,且煅燒而得者)插置於其中而得在吸收蕊型電熱蒸薰裝置內所用的部件。
將各100毫克的本發明化合物(1)至(3)分別溶解於適當量的丙酮中,且使該溶液滲入具有1.2公分厚度的4.0公分×4.0公分多孔型陶瓷板而得加熱性薰劑。
將各100微克(μg)的本發明化合物(1)至(3)分別溶解於適當量的丙酮中,且將該溶液均勻地施加在具有0.3毫米厚度的2公分×2公分濾片上,且將丙酮風乾而得在室溫
下使用的揮發劑。
然後,試驗例證明本發明化合物為害蟲防治劑的有效活性成分。
將各0.025份在上述製造例中製造的本發明化合物(1)至(3)分別溶解在10份的二氯甲烷內,且將該溶液與89.975份的除臭煤油混合而製備0.025%的油性溶液。
將成年家蠅(5雄和5雌,總共10隻)放到每邊各70公分的立方室內,且將0.7毫升的0.025%上述所製本發明化合物油溶液使用噴槍在8.8×104
Pa的壓力透過該室一邊的小窗噴到該室內。在噴布兩分鐘後,計算擊倒的家蠅數目(2重複)。
此外,使用下式所示之(1R)-反-3-(2-甲基-1-丙烯基)-2,2-二甲基環丙烷羧酸4-甲基-2,3,5,6-四氟苯甲基酯:
(在EP0926129A1中所述化合物;後文中稱為比較化合物(1)),下式所示之(1R)-反-3-(2-甲基-1-丙烯基)-2,2-二甲基環丙烷羧酸4-甲氧基-2,3,5,6-四氟苯甲基酯:
(在US4405640中所述化合物;後文中稱為比較化合物
(2)),下式所示之(1R)-反-3-(2-甲基-1-丙烯基)-2,2-二甲基環丙烷羧酸4-烯丙基-2,3,5,6-四氟苯甲基酯:
(在US4405640中所述化合物;後文中稱為比較化合物(3)),取代本發明化合物(1)至(3)作為對照組實施與上述相同的試驗。
其結果顯示於表1中。
將各0.00625份在上述製造例中製造的本發明化合物(1)至(3)分別溶解在10份的二氯甲烷內,且將該溶液與89.99375份的除臭煤油混合而製備0.00625%的油性溶液。
將10隻雌性普通家蚊(Culex pipens pallens)放到每邊各70公分之立方室內,且將0.7毫升的0.00625%上述所製本發明化合物油溶液使用噴槍在8.8×104
Pa的壓力透過該室一邊的小窗噴到該室內。在噴布10分鐘後,將該等雌
性普通家蚊回收於一乾淨杯子(底部直徑8.2公分)內,杯子內裝有含0.5%糖水溶液的脫脂棉,且靜置到隔天。24小時之後,計數死亡的蚊子數目,且計算死亡率(2重複)。
此外,使用(1R)-反-3-(2-氰基-1-丙烯基)-2,2-二甲基環丙烷羧酸4-甲氧基甲基-2,3,5,6-四氟苯甲基酯(關於雙鍵的異構物之比例:Z/E=約2/1)(在US6908945B2中所述化合物;後文中稱為比較化合物(4))作為對照組取代本發明化合物(1)至(3)實施與上述相同的試驗。
其結果顯示於表2中。
由於本發明化合物具有優良的害蟲防治效力,因此其可用為害蟲防治劑的活性成分。
Claims (6)
- 一種式(1)所示之酯化合物:
- 如申請專利範圍第1項之酯化合物,其中,A為單鍵者。
- 如申請專利範圍第1項之酯化合物,其中,A為氧原子者。
- 一種害蟲防治劑,其包含式(1)所示之酯化合物作為活性成分。
- 一種防治害蟲的方法,其包括施加0.1至10000 ppm之濃度之申請專利範圍第4項之害蟲防治劑於害蟲或害蟲棲息之場所。
- 一種式(1)所示之酯化合物之用途,其係用於防治害蟲。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2007048936 | 2007-02-28 | ||
JP2007259566A JP5526472B2 (ja) | 2007-02-28 | 2007-10-03 | エステル化合物及びその用途 |
Publications (2)
Publication Number | Publication Date |
---|---|
TW200848404A TW200848404A (en) | 2008-12-16 |
TWI410405B true TWI410405B (zh) | 2013-10-01 |
Family
ID=39473325
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
TW097105304A TWI410405B (zh) | 2007-02-28 | 2008-02-15 | 酯化合物與其用途 |
Country Status (14)
Country | Link |
---|---|
US (2) | US7968598B2 (zh) |
EP (1) | EP2125708B1 (zh) |
JP (1) | JP5526472B2 (zh) |
KR (1) | KR101442872B1 (zh) |
CN (1) | CN101668733B (zh) |
AR (1) | AR068966A1 (zh) |
AU (1) | AU2008221904B2 (zh) |
BR (1) | BRPI0807989B1 (zh) |
ES (1) | ES2540563T3 (zh) |
MX (1) | MX2009009041A (zh) |
MY (1) | MY148668A (zh) |
RU (1) | RU2449986C2 (zh) |
TW (1) | TWI410405B (zh) |
WO (1) | WO2008108376A1 (zh) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5526472B2 (ja) * | 2007-02-28 | 2014-06-18 | 住友化学株式会社 | エステル化合物及びその用途 |
DE102008038070A1 (de) * | 2008-08-16 | 2010-02-18 | Clariant International Ltd. | Trockene Pigmentpräparationen mit nichtionischen Additiven |
CN102361851B (zh) * | 2009-03-23 | 2014-03-19 | 住友化学株式会社 | 环丙烷甲酸酯的制造方法 |
EP2418197B1 (en) * | 2009-04-06 | 2014-05-07 | Sumitomo Chemical Company, Limited | Process for producing 3-(2-cyano-1-propenyl)-2,2- dimethylcyclopropanecarboxylic acid or salt thereof |
JP5655527B2 (ja) | 2009-12-02 | 2015-01-21 | 住友化学株式会社 | (z)−シアノアルケニルシクロプロパンカルボン酸化合物の製造方法 |
JP5760473B2 (ja) | 2010-02-12 | 2015-08-12 | 住友化学株式会社 | シアノアルケニルシクロプロパンカルボン酸の製造方法 |
WO2011122509A1 (en) * | 2010-03-31 | 2011-10-06 | Sumitomo Chemical Company, Limited | Ester compound and use thereof |
CN102822143B (zh) * | 2010-03-31 | 2015-04-22 | 住友化学株式会社 | 作为杀虫剂的拟除虫菊酯型酯 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4405640A (en) * | 1979-12-21 | 1983-09-20 | Imperial Chemical Industries Plc | Substituted fluorobenzyl cyclopropane carboxylates useful as insecticides |
EP0448427A1 (fr) * | 1990-02-27 | 1991-09-25 | Roussel-Uclaf | Nouveaux esters dérivés d'acide 3-[2-cyano 2-halogéno éthényl], 2,2-diméthyl cyclopropanecarboxylique,leur procédé de préparation et leur application comme pesticides |
EP0926129A1 (en) * | 1997-12-03 | 1999-06-30 | Sumitomo Chemical Company, Limited | Ester compound and pesticide containing it |
US20030195119A1 (en) * | 2002-04-12 | 2003-10-16 | Tatsuya Mori | Ester compound and its use |
EP1462441A1 (en) * | 2001-12-11 | 2004-09-29 | Sumitomo Chemical Company, Limited | Cyclopropanecarboxylic acid esters and pest controllers containing the same |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4370346A (en) * | 1979-12-21 | 1983-01-25 | Imperial Chemical Industries Plc | Halogenated esters |
JP4285045B2 (ja) * | 2002-04-12 | 2009-06-24 | 住友化学株式会社 | エステル化合物およびその用途 |
TWI370812B (en) | 2006-01-23 | 2012-08-21 | Sumitomo Chemical Co | Ester compound and its use |
JP5526472B2 (ja) * | 2007-02-28 | 2014-06-18 | 住友化学株式会社 | エステル化合物及びその用途 |
-
2007
- 2007-10-03 JP JP2007259566A patent/JP5526472B2/ja active Active
-
2008
- 2008-02-15 TW TW097105304A patent/TWI410405B/zh not_active IP Right Cessation
- 2008-02-27 ES ES08721304.7T patent/ES2540563T3/es active Active
- 2008-02-27 BR BRPI0807989-7A patent/BRPI0807989B1/pt not_active IP Right Cessation
- 2008-02-27 EP EP08721304.7A patent/EP2125708B1/en not_active Not-in-force
- 2008-02-27 WO PCT/JP2008/053884 patent/WO2008108376A1/en active Application Filing
- 2008-02-27 KR KR1020097020026A patent/KR101442872B1/ko not_active IP Right Cessation
- 2008-02-27 AR ARP080100798A patent/AR068966A1/es unknown
- 2008-02-27 US US12/528,528 patent/US7968598B2/en not_active Expired - Fee Related
- 2008-02-27 CN CN2008800136930A patent/CN101668733B/zh active Active
- 2008-02-27 AU AU2008221904A patent/AU2008221904B2/en not_active Ceased
- 2008-02-27 MX MX2009009041A patent/MX2009009041A/es active IP Right Grant
- 2008-02-27 RU RU2009135804/04A patent/RU2449986C2/ru not_active IP Right Cessation
- 2008-02-27 MY MYPI20093539A patent/MY148668A/en unknown
-
2010
- 2010-11-17 US US12/947,852 patent/US8367724B2/en active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4405640A (en) * | 1979-12-21 | 1983-09-20 | Imperial Chemical Industries Plc | Substituted fluorobenzyl cyclopropane carboxylates useful as insecticides |
EP0448427A1 (fr) * | 1990-02-27 | 1991-09-25 | Roussel-Uclaf | Nouveaux esters dérivés d'acide 3-[2-cyano 2-halogéno éthényl], 2,2-diméthyl cyclopropanecarboxylique,leur procédé de préparation et leur application comme pesticides |
EP0926129A1 (en) * | 1997-12-03 | 1999-06-30 | Sumitomo Chemical Company, Limited | Ester compound and pesticide containing it |
EP1462441A1 (en) * | 2001-12-11 | 2004-09-29 | Sumitomo Chemical Company, Limited | Cyclopropanecarboxylic acid esters and pest controllers containing the same |
US20030195119A1 (en) * | 2002-04-12 | 2003-10-16 | Tatsuya Mori | Ester compound and its use |
Also Published As
Publication number | Publication date |
---|---|
JP2008239597A (ja) | 2008-10-09 |
MX2009009041A (es) | 2009-08-31 |
RU2009135804A (ru) | 2011-04-10 |
JP5526472B2 (ja) | 2014-06-18 |
MY148668A (en) | 2013-05-31 |
AU2008221904B2 (en) | 2012-04-19 |
KR101442872B1 (ko) | 2014-09-19 |
CN101668733B (zh) | 2013-12-11 |
TW200848404A (en) | 2008-12-16 |
ES2540563T3 (es) | 2015-07-10 |
KR20100014578A (ko) | 2010-02-10 |
US20100035985A1 (en) | 2010-02-11 |
US8367724B2 (en) | 2013-02-05 |
BRPI0807989A2 (pt) | 2014-06-17 |
BRPI0807989B1 (pt) | 2018-07-31 |
AU2008221904A1 (en) | 2008-09-12 |
US20110065789A1 (en) | 2011-03-17 |
CN101668733A (zh) | 2010-03-10 |
US7968598B2 (en) | 2011-06-28 |
EP2125708A1 (en) | 2009-12-02 |
EP2125708B1 (en) | 2015-06-17 |
WO2008108376A1 (en) | 2008-09-12 |
RU2449986C2 (ru) | 2012-05-10 |
AR068966A1 (es) | 2009-12-23 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US6908945B2 (en) | Ester compound and its use | |
US7217682B2 (en) | Cyclopropanecarboxylic acid esters and pest controllers containing the same | |
US7700648B2 (en) | Ester compound and its use | |
TWI410405B (zh) | 酯化合物與其用途 | |
US20090253763A1 (en) | Ester compound and its use | |
TWI403268B (zh) | 酯化合物及其用途 | |
EP1976386B1 (en) | Ester compound and its use | |
US7569603B2 (en) | Ester compound and its use in pest control | |
AU2007250934B2 (en) | Ester compound and its use in pest control |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
MM4A | Annulment or lapse of patent due to non-payment of fees |